PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o366–o367.
Published online 2010 January 16. doi:  10.1107/S1600536810000280
PMCID: PMC2979907

Trimipraminium maleate

Abstract

The title compound [systematic name: 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N,2-trimethyl­propan-1-aminium hydrogen maleate], C20H27N2 +·C4H3O4 , a maleate salt of trimipramine, crystallizes with four independent cation–anion pairs in the asymmetric unit. The trimipramine cation contains a seven-membered azepine ring with two fused benzene rings whose mean planes are separated by 51.7 (1)°. Inter­molecular N—H(...)O and intra­molecular O—H(...)O hydrogen bonds pack the ions into chains along [101]. Additional weak inter­molecular C—H(...)O inter­actions help to influence the twist angles of the mean planes of the benzene rings fused to the azepine ring in the cation. A geometry-optimized MOPAC AM1 theoretical calculation supports these observations.

Related literature

For refractory depression treatment, see: Broquet, (1999 [triangle]). For tricyclic anti­depressant treatment, see: Biederman et al. (1989 [triangle]). For treatment of depression, see: Al-Badr, (1983 [triangle]); Al-Badr & Ibrahim (1979 [triangle]); Lapierre, (1989 [triangle]). For protonation of trimipramine salts of maleate, mesylate and hydro­chloride observed by 1H, 13C and 15N NMR, see: Somashekar et al. (2004 [triangle]). For the PMR spectrometric analysis of trimipramine maleate in pharmaceutical preparations, see: Al-Badr & Ibrahim (1979 [triangle]). For related structures, see: Bindya et al. (2007 [triangle]); Harrison, Bindya et al. (2007 [triangle]); Harrison, Swamy et al. (2007 [triangle]); Jones et al. (1978 [triangle]); Kamel et al. (2001 [triangle]); Portalone et al. (2007 [triangle]); Post et al. (1975 [triangle]); Swamy et al. (2007 [triangle]). For MOPAC AM1 calculations, see: Schmidt & Polik (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o366-scheme1.jpg

Experimental

Crystal data

  • C20H27N2 +·C4H3O4
  • M r = 410.50
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o366-efi1.jpg
  • a = 19.4356 (4) Å
  • b = 11.0542 (4) Å
  • c = 40.4107 (13) Å
  • V = 8682.0 (5) Å3
  • Z = 16
  • Cu Kα radiation
  • μ = 0.69 mm−1
  • T = 110 K
  • 0.51 × 0.42 × 0.12 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.576, T max = 1.000
  • 27150 measured reflections
  • 13174 (8810) independent reflections
  • 10894 (7507) reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.095
  • S = 0.96
  • 13174 reflections
  • 1099 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.20 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 8810 Friedel pairs
  • Flack parameter: −0.14 (13)

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000280/ng2715sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000280/ng2715Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

QNMHA thanks the University of Mysore for use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

The title compound is a derivative of trimipramine, chemically, 5-(3-dimethylamino-2-methylpropyl)-10,11-dihydro-5H-dibenz(b,f)azepine maleate, a tricyclic antidepressant with sedative and anxiolytic properties and available as stangyl, surmontil, rhotrimine and generic forms. Tricyclic antidepressants are sometimes still used to treat refractory depression that has failed to respond to standard SSRI therapy (Broquet, 1999). Tricyclic antidepressants have been shown to be effective in treating attention-deficit hyperactivity disorder(ADHD) (Biederman et al., 1989). ADHD is thought to be caused by dopamine and norepinephrine shortages in the brain's prefrontal cortex.

Trimipramine is a tricyclic antidepressant of the dibenzazepine class with sedative properties. It also has anticholinergic properties and potentiates the sympathetic response, presumably by blocking the reuptake of norepinephrine which has been released by the presynaptic neurons. It has a quinidine like effect on the heart and an EEG activity similar to that of other tricyclic antidepressants. Trimipramine is a serotonin transport blocker that also blocks norepinephrine uptake. The mechanism of action of trimipramine differs from other tricyclic antidepressants. It is only a moderate reuptake inhibitor of norepinephrine, and a weak reuptake inhibitor of serotonin and dopamine. The spectrum of effects (strong antidepressant activity, sedation and anxiolysis) and side-effects (strong anticholinergic and antiadrenergic side-effects) is the same as with Doxepin. It is also a more effective sedative than amitriptyline. Trimipramine is the only effective drug against insomnia known so far that does not alter the normal sleep architecture.

Trimipramine maleate salt is used in the treatment of depression as well as peptic ulcer and severe chronic pain. A comprehensive description of the title compound is described (Al-Badr, 1983; Lapierre, 1989). The protonation of trimipramine salts of maleate, mesylate and hydrochloride observed by 1H, 13C and 15N NMR spectroscopy is reported (Somashekar et al., 2004). Also, the PMR spectrometric analysis of trimipramine maleate in pharmaceutical preparation is described (Al-Badr & Ibrahim, 1979). The related crystal structures viz., imipramine hydrochloride (Post et al., 1975), 5-(3-dimethylammonioprop-1-enylidene)-5H-dibenzo[a,d]cycloheptene maleate (Jones et al., 1978), desipraminium picrate (Swamy et al., 2007), desipraminium picrate monohydrate (Harrison, Swamy et al., 2007), imipraminium picrate (Harrison, Bindya et al., 2007), amitriptylinium picrate (Bindya et al., 2007), 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[a,d][7]annulen-5-ol (Portalone et al., 2007) have been reported. In view of the importance of the title compound, a crystal structure is reported.

The title compound, C20H27N2+. C4H3O4-, a maleate salt of trimipramine, crystallizes with four independent cation-anion pairs (E—A, Fig.1; F—B, Fig. 2; G—C, Fig. 3; H—D, Fig. 4) in the asymmetric unit. Bond lengths and bond angles are all within expected ranges (Allen et al. 1987). The Trimipramine cation, C20H27N2+, contains a seven-membered azepine ring with two fused benzene rings whose mean planes are separated by 51.3 (8)° [E], 51.7 (6)° [F], 49.9 (0)° [G], and 53.9 (0)° [H], respectively. These angles are all less than 57;1(1)° reported for bis((3-(10,11-Dihydro-dibenzo(b,f)azepin-5-yl)-2-methyl-propyl) dimethylammonium) tetrachlorocuprate(ii) (Kamel et al. 2001), which contains an identical cation. Intermolecular N—H···O and intramolecular O—H···O hydrogen bonds (Table 1, Fig. 5) pack the ions into chains along the [101]. Additional weak C—H···O intermolecular interactions (Table 1) help to significantly influence the twist angles of the mean planes of the benzene rings fused to the azepine ring in the cation. After a geometry optimimized MOPAC AM1 calculation with WebMO Pro (Schmidt & Polik 2007) on the cation fragment, in vacuo, the dihedral angle between the mean planes of the two benzene rings of the azepine group becomes 51.3 (8)°, which is slightly less than the average of the four indepentent cations (51.7 (1)° but nearly 6° less than that observed in the tetrachlorocuprate (ii) analogue compound. These observations support the suggestion that these intra and intermolecular interactions influence crystal packing in the title compound.

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore, India. The compound was used without further purification. X-ray quality crystals (m.p. 410–412 K) were obtained by slow evaporation from methanol solution.

Refinement

All of the H atoms were placed in their calculated positions and then refined using the riding model with O–H = 0.84 Å, N–H = 0.93 Å, C–H = 0.95–1.00 Å, and with Uiso(H) = 1.19–2.23Ueq(O), Uiso(H) = 1.18–1.21eq(N), Uiso(H) = 1.18–1.51Ueq(C).

Figures

Fig. 1.
ORTEP drawings of cation E (C20H27N2+) and anion A (C4H3O4-) in the asymmetric unit of (I) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-H atoms. Dashed lines indicate N2E—H2EB···O2A ...
Fig. 2.
ORTEP drawings of cation F (C20H27N2+) and anion B (C4H3O4-) in the asymmetric unit of (I) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-H atoms. Dashed lines indicate N2F—H2FB···O2B ...
Fig. 3.
ORTEP drawings of cation G (C20H27N2+) and anion C (C4H3O4-) in the asymmetric unit of (I) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-H atoms. Dashed lines indicate N2G—H2GB···O2C ...
Fig. 4.
ORTEP drawings of cation H (C20H27N2+) and anion D (C4H3O4-) in the asymmetric unit of (I) showing the atom numbering scheme and 50% probability displacement ellipsoids of non-H atoms. Dashed lines indicate N2H—H2HB···O4C ...
Fig. 5.
The molecular packing for (I) viewed down the b axis. Dashed lines indicate cation C20H27N2+ and anion C4H3O4- inter and intramolecular hydrogen bond interactions linking the ions into chains along the [101].

Crystal data

C20H27N2+·C4H3O4F(000) = 3520
Mr = 410.50Dx = 1.256 Mg m3
Orthorhombic, Pna21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2nCell parameters from 11412 reflections
a = 19.4356 (4) Åθ = 4.0–74.2°
b = 11.0542 (4) ŵ = 0.69 mm1
c = 40.4107 (13) ÅT = 110 K
V = 8682.0 (5) Å3Plate, colorless
Z = 160.51 × 0.42 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector13174 (8810) independent reflections
Radiation source: Enhance (Cu) X-ray Source10894 (7507) reflections with I > 2σ(I)
graphiteRint = 0.030
Detector resolution: 10.5081 pixels mm-1θmax = 74.3°, θmin = 4.2°
ω scansh = −24→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)k = −13→10
Tmin = 0.576, Tmax = 1.000l = −49→33
27150 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.095w = 1/[σ2(Fo2) + (0.0612P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
13174 reflectionsΔρmax = 0.25 e Å3
1099 parametersΔρmin = −0.20 e Å3
1 restraintAbsolute structure: Flack (1983), 8810 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.14 (13)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1A0.58175 (9)0.66955 (15)0.87821 (5)0.0343 (4)
O2A0.50638 (8)0.54786 (16)0.90212 (5)0.0357 (4)
O3A0.70323 (9)0.66032 (16)0.86344 (5)0.0351 (4)
H3A0.66000.66190.86400.042*
O4A0.78569 (8)0.52450 (18)0.86994 (4)0.0362 (4)
C1A0.56195 (11)0.5666 (2)0.88763 (6)0.0271 (5)
C2A0.60653 (12)0.4573 (2)0.88168 (6)0.0267 (5)
H2AA0.58380.38160.88370.032*
C3A0.67296 (12)0.4509 (2)0.87401 (6)0.0268 (5)
H3AA0.69040.37120.87130.032*
C4A0.72470 (12)0.5500 (2)0.86899 (6)0.0282 (5)
O1B0.66282 (9)0.16974 (15)0.81349 (5)0.0348 (4)
O2B0.73716 (8)0.04584 (16)0.78925 (5)0.0350 (4)
O3B0.54116 (9)0.16247 (16)0.82794 (5)0.0341 (4)
H3B0.58110.16990.82030.041*
O4B0.45786 (8)0.02889 (18)0.82187 (4)0.0356 (4)
C1B0.68199 (11)0.0647 (2)0.80384 (6)0.0254 (5)
C2B0.63673 (12)−0.0427 (2)0.80977 (6)0.0281 (5)
H2BA0.6588−0.11900.80790.034*
C3B0.57009 (12)−0.0470 (2)0.81730 (6)0.0279 (5)
H3BA0.5518−0.12630.81970.033*
C4B0.51926 (12)0.0532 (2)0.82266 (6)0.0265 (5)
O1C1.00950 (9)−0.19360 (17)0.77304 (6)0.0425 (5)
O2C0.93067 (8)−0.10531 (15)0.80408 (5)0.0326 (4)
O3C1.12417 (9)−0.15162 (18)0.75295 (6)0.0455 (5)
H3C1.0849−0.16820.76030.058 (10)*
O4C1.20222 (9)−0.00892 (17)0.75951 (5)0.0406 (5)
C1C0.98947 (12)−0.1100 (2)0.79234 (6)0.0273 (5)
C2C1.03816 (12)−0.0089 (2)0.80136 (6)0.0294 (5)
H2CA1.02110.04670.81730.035*
C3C1.10112 (12)0.0141 (2)0.79044 (6)0.0310 (5)
H3CA1.12150.08460.79960.037*
C4C1.14567 (12)−0.0517 (2)0.76614 (7)0.0310 (5)
O1D0.12050 (9)0.34429 (18)0.93976 (6)0.0446 (5)
O2D0.04202 (9)0.48725 (17)0.93376 (6)0.0442 (5)
O3D0.23541 (9)0.30437 (18)0.91934 (6)0.0430 (5)
H3D0.19510.31770.92590.096 (15)*
O4D0.31337 (8)0.39596 (16)0.88852 (5)0.0351 (4)
C1D0.09837 (12)0.4447 (2)0.92666 (7)0.0341 (6)
C2D0.14201 (12)0.5106 (2)0.90230 (7)0.0321 (5)
H2DA0.12110.58080.89320.039*
C3D0.20512 (12)0.4883 (2)0.89104 (6)0.0314 (5)
H3DA0.22140.54330.87480.038*
C4D0.25439 (12)0.3894 (2)0.90020 (6)0.0297 (5)
N1E0.31557 (10)0.86746 (19)0.99160 (5)0.0269 (4)
N2E0.41974 (12)0.74274 (17)0.90465 (6)0.0244 (5)
H2EB0.45480.68760.90890.029*
C1E0.27203 (14)0.7645 (2)0.99710 (7)0.0281 (6)
C2E0.28481 (13)0.6814 (2)1.02218 (7)0.0331 (5)
H2EA0.32290.69221.03660.040*
C3E0.24138 (15)0.5821 (3)1.02605 (8)0.0440 (7)
H3EA0.25040.52421.04280.053*
C4E0.18535 (15)0.5679 (3)1.00553 (9)0.0506 (8)
H4EA0.15540.50091.00840.061*
C5E0.17267 (14)0.6509 (3)0.98078 (8)0.0455 (7)
H5EA0.13390.64010.96680.055*
C6E0.21557 (15)0.7504 (3)0.97584 (8)0.0357 (7)
C7E0.20514 (14)0.8394 (3)0.94861 (7)0.0459 (8)
H7EA0.16960.80790.93330.055*
H7EB0.24860.84750.93600.055*
C8E0.18330 (15)0.9626 (3)0.96072 (7)0.0478 (8)
H8EA0.13720.95400.97090.057*
H8EB0.17791.01540.94110.057*
C9E0.22917 (13)1.0293 (3)0.98546 (6)0.0351 (6)
C10E0.20910 (14)1.1469 (3)0.99337 (8)0.0430 (7)
H10A0.16911.17940.98310.052*
C11E0.24513 (15)1.2180 (3)1.01551 (10)0.0504 (8)
H11A0.23051.29831.02010.060*
C12E0.30230 (15)1.1711 (3)1.03075 (9)0.0474 (7)
H12A0.32711.21861.04630.057*
C13E0.32394 (13)1.0545 (3)1.02359 (7)0.0366 (6)
H13A0.36321.02271.03460.044*
C14E0.28892 (12)0.9827 (2)1.00042 (6)0.0291 (5)
C15E0.38988 (12)0.8465 (2)0.99454 (6)0.0275 (5)
H15A0.40010.81211.01660.033*
H15B0.41450.92460.99260.033*
C16E0.41544 (15)0.7607 (2)0.96804 (7)0.0281 (6)
H16A0.38500.68780.96750.034*
C17E0.48914 (13)0.7210 (3)0.97591 (8)0.0363 (6)
H17A0.48980.67760.99700.054*
H17B0.51880.79250.97740.054*
H17C0.50600.66770.95830.054*
C18E0.41246 (12)0.8238 (2)0.93451 (6)0.0268 (5)
H18A0.36800.86720.93290.032*
H18B0.44940.88540.93370.032*
C19E0.35584 (13)0.6736 (2)0.89740 (7)0.0358 (6)
H19A0.36540.61240.88040.054*
H19B0.32020.72900.88930.054*
H19C0.33980.63360.91760.054*
C20E0.44040 (13)0.8170 (2)0.87571 (6)0.0320 (5)
H20A0.40470.87740.87110.048*
H20B0.44620.76460.85630.048*
H20C0.48390.85810.88050.048*
N1F0.93298 (9)0.36019 (18)0.70040 (5)0.0253 (4)
N2F0.82441 (11)0.23990 (17)0.78662 (6)0.0240 (5)
H2FB0.78930.18500.78230.029*
C1F0.96070 (11)0.4777 (2)0.69341 (6)0.0254 (5)
C2F0.92522 (13)0.5557 (2)0.67222 (6)0.0316 (5)
H2FA0.88550.52710.66100.038*
C3F0.94676 (14)0.6740 (3)0.66720 (7)0.0392 (6)
H3FA0.92180.72570.65280.047*
C4F1.00465 (14)0.7161 (3)0.68330 (8)0.0431 (7)
H4FA1.01920.79760.68070.052*
C5F1.04099 (13)0.6379 (2)0.70325 (7)0.0365 (6)
H5FA1.08120.66720.71390.044*
C6F1.02187 (12)0.5185 (2)0.70856 (6)0.0302 (5)
C7F1.06982 (14)0.4437 (3)0.72995 (7)0.0405 (6)
H7FA1.11280.43060.71730.049*
H7FB1.08190.49280.74960.049*
C8F1.04523 (13)0.3215 (3)0.74211 (6)0.0395 (6)
H8FA1.08050.28600.75690.047*
H8FB1.00250.33220.75510.047*
C9F1.03169 (14)0.2364 (3)0.71393 (7)0.0314 (6)
C10F1.07402 (13)0.1371 (3)0.70710 (7)0.0400 (6)
H10B1.11340.12320.72050.048*
C11F1.05974 (14)0.0586 (2)0.68125 (8)0.0433 (7)
H11B1.0891−0.00830.67700.052*
C12F1.00240 (14)0.0786 (3)0.66168 (8)0.0394 (6)
H12B0.99160.02440.64420.047*
C13F0.96095 (13)0.1777 (2)0.66772 (6)0.0312 (5)
H13B0.92200.19160.65400.037*
C14F0.97509 (15)0.2575 (2)0.69345 (7)0.0257 (6)
C15F0.85855 (11)0.3432 (2)0.69700 (6)0.0267 (5)
H15C0.84820.31030.67480.032*
H15D0.83500.42220.69920.032*
C16F0.83121 (14)0.2554 (2)0.72370 (7)0.0248 (6)
H16B0.86200.18300.72480.030*
C17F0.75860 (12)0.2147 (3)0.71426 (7)0.0339 (6)
H17D0.72830.28540.71290.051*
H17E0.74110.15880.73110.051*
H17F0.75990.17370.69280.051*
C18F0.83306 (11)0.3199 (2)0.75661 (6)0.0253 (5)
H18C0.79620.38170.75680.030*
H18D0.87750.36300.75850.030*
C19F0.80369 (13)0.3156 (2)0.81538 (6)0.0318 (5)
H19D0.75930.35420.81070.048*
H19E0.83860.37800.81930.048*
H19F0.79950.26450.83510.048*
C20F0.88810 (12)0.1709 (2)0.79412 (7)0.0341 (6)
H20D0.92440.22700.80110.051*
H20E0.90300.12710.77430.051*
H20F0.87890.11300.81200.051*
N1G0.75577 (11)−0.1416 (2)0.66359 (5)0.0264 (4)
N2G0.84294 (11)−0.26844 (19)0.77420 (6)0.0255 (5)
H2GB0.8733−0.20570.77890.031*
C1G0.73378 (13)−0.0364 (2)0.64615 (6)0.0261 (5)
C2G0.66948 (12)0.0151 (2)0.65213 (6)0.0291 (5)
H2GA0.6382−0.02410.66670.035*
C3G0.65072 (13)0.1227 (3)0.63715 (6)0.0353 (6)
H3GA0.60760.15910.64210.042*
C4G0.69555 (14)0.1771 (3)0.61487 (7)0.0420 (6)
H4GA0.68280.25000.60410.050*
C5G0.75887 (14)0.1248 (3)0.60840 (7)0.0380 (6)
H5GA0.78920.16240.59310.046*
C6G0.77886 (12)0.0179 (2)0.62392 (6)0.0290 (5)
C7G0.84630 (12)−0.0437 (2)0.61698 (6)0.0304 (5)
H7GA0.8702−0.06010.63810.037*
H7GB0.87580.01070.60370.037*
C8G0.83590 (14)−0.1622 (2)0.59839 (6)0.0352 (6)
H8GA0.8104−0.14410.57780.042*
H8GB0.8818−0.19290.59180.042*
C9G0.79819 (15)−0.2637 (2)0.61629 (8)0.0304 (6)
C10G0.80278 (14)−0.3780 (3)0.60162 (7)0.0375 (6)
H10C0.8269−0.38550.58130.045*
C11G0.77363 (14)−0.4813 (2)0.61541 (7)0.0377 (6)
H11C0.7772−0.55730.60460.045*
C12G0.73934 (14)−0.4708 (3)0.64528 (7)0.0343 (6)
H12C0.7194−0.54030.65520.041*
C13G0.73412 (13)−0.3593 (2)0.66065 (7)0.0302 (5)
H13C0.7108−0.35370.68120.036*
C14G0.76249 (14)−0.2538 (2)0.64662 (8)0.0286 (6)
C15G0.74368 (12)−0.1426 (2)0.69948 (6)0.0263 (5)
H15E0.7049−0.19760.70460.032*
H15F0.7309−0.06030.70690.032*
C16G0.80829 (11)−0.1847 (2)0.71815 (6)0.0235 (4)
H16C0.8269−0.25850.70700.028*
C17G0.86398 (12)−0.0872 (2)0.71826 (6)0.0284 (5)
H17G0.9069−0.12130.72690.043*
H17H0.8494−0.01970.73230.043*
H17I0.8714−0.05810.69560.043*
C18G0.78581 (11)−0.2186 (2)0.75302 (6)0.0244 (5)
H18E0.7665−0.14600.76400.029*
H18F0.7487−0.27970.75160.029*
C19G0.88225 (13)−0.3668 (2)0.75776 (7)0.0337 (6)
H19G0.9099−0.33270.73970.051*
H19H0.8502−0.42670.74880.051*
H19I0.9127−0.40570.77390.051*
C20G0.81334 (14)−0.3117 (3)0.80586 (6)0.0408 (7)
H20G0.8502−0.34310.82000.061*
H20H0.7800−0.37610.80140.061*
H20I0.7903−0.24440.81710.061*
N1H0.49061 (10)0.37169 (19)1.02777 (5)0.0269 (4)
N2H0.40102 (11)0.23369 (18)0.91833 (5)0.0243 (4)
H2HB0.37010.29560.91370.029*
C1H0.51240 (12)0.4799 (2)1.04358 (6)0.0247 (5)
C2H0.57518 (11)0.5346 (2)1.03544 (6)0.0263 (5)
H2HA0.60630.49361.02120.032*
C3H0.59269 (13)0.6468 (2)1.04776 (6)0.0307 (5)
H3HA0.63480.68381.04150.037*
C4H0.54832 (14)0.7055 (2)1.06947 (6)0.0332 (5)
H4HA0.55960.78331.07790.040*
C5H0.48754 (13)0.6495 (2)1.07870 (6)0.0329 (5)
H5HA0.45810.68871.09410.039*
C6H0.46838 (12)0.5377 (2)1.06605 (6)0.0289 (5)
C7H0.40374 (13)0.4722 (2)1.07605 (7)0.0338 (6)
H7HA0.37690.45211.05600.041*
H7HB0.37530.52641.09000.041*
C8H0.41876 (14)0.3567 (2)1.09509 (7)0.0356 (6)
H8HA0.37440.32481.10340.043*
H8HB0.44670.37861.11470.043*
C9H0.45548 (15)0.2541 (2)1.07722 (8)0.0304 (6)
C10H0.45524 (15)0.1421 (3)1.09310 (7)0.0381 (6)
H10D0.43460.13651.11430.046*
C11H0.48362 (15)0.0387 (3)1.07943 (7)0.0408 (6)
H11D0.4825−0.03591.09110.049*
C12H0.51347 (14)0.0462 (3)1.04862 (8)0.0360 (6)
H12D0.5327−0.02391.03870.043*
C13H0.51540 (13)0.1555 (2)1.03216 (7)0.0304 (6)
H13D0.53620.15941.01090.036*
C14H0.48756 (14)0.2608 (2)1.04588 (7)0.0253 (6)
C15H0.50098 (12)0.3667 (2)0.99175 (6)0.0259 (5)
H15G0.54040.31320.98670.031*
H15H0.51200.44870.98340.031*
C16H0.43646 (11)0.3190 (2)0.97420 (5)0.0230 (4)
H16D0.41990.24490.98590.028*
C17H0.37928 (13)0.4145 (2)0.97456 (6)0.0311 (5)
H17J0.33680.37910.96580.047*
H17K0.39300.48350.96080.047*
H17L0.37150.44180.99730.047*
C18H0.45769 (11)0.2851 (2)0.93916 (6)0.0249 (5)
H18G0.47600.35810.92800.030*
H18H0.49540.22510.94040.030*
C19H0.36263 (13)0.1349 (2)0.93551 (7)0.0328 (5)
H19J0.39540.07640.94470.049*
H19K0.33230.09400.91970.049*
H19L0.33500.16940.95350.049*
C20H0.43019 (14)0.1898 (3)0.88633 (6)0.0410 (7)
H20J0.39300.15800.87240.062*
H20K0.46380.12550.89070.062*
H20L0.45290.25700.87490.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0264 (8)0.0255 (9)0.0511 (11)0.0021 (7)0.0053 (8)0.0026 (8)
O2A0.0243 (8)0.0330 (10)0.0499 (11)0.0059 (7)0.0081 (8)0.0059 (9)
O3A0.0276 (8)0.0313 (10)0.0465 (10)−0.0024 (7)0.0093 (8)0.0039 (8)
O4A0.0220 (8)0.0487 (12)0.0379 (10)0.0008 (8)0.0032 (7)0.0018 (8)
C1A0.0234 (11)0.0286 (12)0.0292 (12)0.0029 (9)−0.0016 (9)0.0002 (10)
C2A0.0260 (11)0.0226 (11)0.0315 (12)−0.0015 (9)−0.0006 (9)−0.0007 (10)
C3A0.0287 (11)0.0250 (12)0.0269 (11)0.0041 (9)0.0009 (9)0.0000 (10)
C4A0.0250 (11)0.0359 (14)0.0237 (11)−0.0005 (10)0.0049 (9)−0.0016 (10)
O1B0.0273 (8)0.0257 (9)0.0515 (11)−0.0049 (7)0.0031 (8)−0.0010 (8)
O2B0.0241 (8)0.0333 (10)0.0474 (10)−0.0062 (7)0.0085 (8)−0.0049 (8)
O3B0.0274 (8)0.0306 (9)0.0444 (10)0.0003 (7)0.0090 (8)−0.0037 (8)
O4B0.0223 (8)0.0465 (11)0.0380 (9)−0.0021 (8)0.0020 (7)−0.0029 (8)
C1B0.0199 (10)0.0263 (12)0.0299 (11)−0.0015 (9)−0.0030 (9)0.0005 (10)
C2B0.0254 (11)0.0239 (12)0.0349 (12)0.0003 (9)0.0003 (10)−0.0006 (10)
C3B0.0285 (11)0.0237 (12)0.0314 (12)−0.0056 (9)0.0043 (10)−0.0003 (10)
C4B0.0244 (11)0.0321 (13)0.0232 (11)0.0022 (9)0.0025 (9)−0.0017 (10)
O1C0.0267 (9)0.0285 (10)0.0724 (14)−0.0056 (7)0.0036 (9)−0.0166 (10)
O2C0.0245 (8)0.0290 (9)0.0444 (10)−0.0031 (7)−0.0001 (7)−0.0015 (8)
O3C0.0236 (9)0.0405 (11)0.0723 (14)−0.0030 (8)0.0073 (9)−0.0183 (10)
O4C0.0245 (8)0.0332 (10)0.0641 (13)−0.0037 (7)−0.0001 (8)0.0035 (9)
C1C0.0242 (11)0.0219 (11)0.0359 (12)0.0001 (9)−0.0075 (9)0.0030 (10)
C2C0.0293 (11)0.0239 (12)0.0350 (13)−0.0026 (10)−0.0073 (10)−0.0005 (10)
C3C0.0308 (12)0.0253 (12)0.0370 (13)−0.0035 (10)−0.0091 (10)−0.0026 (10)
C4C0.0208 (11)0.0259 (12)0.0462 (15)0.0011 (9)−0.0085 (10)0.0028 (11)
O1D0.0253 (8)0.0376 (11)0.0709 (14)0.0037 (8)0.0037 (9)0.0152 (10)
O2D0.0228 (8)0.0337 (10)0.0760 (14)0.0026 (7)−0.0012 (9)−0.0054 (10)
O3D0.0252 (9)0.0327 (11)0.0710 (14)0.0042 (8)0.0023 (9)0.0125 (10)
O4D0.0242 (8)0.0327 (10)0.0484 (11)0.0015 (7)−0.0024 (8)0.0007 (8)
C1D0.0219 (11)0.0301 (13)0.0502 (15)−0.0006 (10)−0.0084 (11)−0.0060 (12)
C2D0.0264 (11)0.0276 (13)0.0424 (14)0.0068 (10)−0.0098 (10)−0.0009 (11)
C3D0.0307 (12)0.0289 (13)0.0346 (13)−0.0013 (10)−0.0061 (10)0.0006 (11)
C4D0.0263 (12)0.0247 (12)0.0382 (13)0.0002 (9)−0.0055 (10)−0.0046 (11)
N1E0.0204 (9)0.0335 (11)0.0268 (9)−0.0042 (8)−0.0018 (8)0.0008 (8)
N2E0.0196 (10)0.0216 (11)0.0322 (12)0.0011 (7)0.0000 (9)0.0015 (8)
C1E0.0226 (12)0.0321 (14)0.0296 (14)−0.0005 (9)0.0041 (11)−0.0071 (10)
C2E0.0282 (12)0.0327 (14)0.0384 (13)−0.0020 (10)0.0061 (10)−0.0022 (11)
C3E0.0414 (15)0.0305 (14)0.0600 (18)−0.0016 (12)0.0175 (14)−0.0001 (13)
C4E0.0321 (14)0.0368 (15)0.083 (2)−0.0147 (12)0.0217 (15)−0.0220 (16)
C5E0.0238 (12)0.0530 (18)0.0596 (18)−0.0012 (12)0.0018 (12)−0.0288 (15)
C6E0.0195 (13)0.0514 (19)0.0363 (16)0.0011 (10)0.0028 (12)−0.0146 (12)
C7E0.0246 (12)0.083 (2)0.0296 (13)0.0070 (13)−0.0057 (10)−0.0100 (14)
C8E0.0366 (14)0.078 (2)0.0284 (13)0.0195 (14)−0.0051 (11)0.0016 (14)
C9E0.0290 (12)0.0480 (16)0.0282 (12)−0.0004 (11)0.0073 (10)0.0130 (11)
C10E0.0319 (13)0.0404 (15)0.0568 (17)0.0069 (12)0.0155 (13)0.0199 (14)
C11E0.0326 (14)0.0306 (14)0.088 (2)−0.0045 (12)0.0231 (15)−0.0005 (16)
C12E0.0338 (13)0.0391 (16)0.069 (2)−0.0121 (12)0.0109 (14)−0.0151 (14)
C13E0.0255 (12)0.0413 (15)0.0431 (14)−0.0072 (10)0.0027 (10)−0.0027 (12)
C14E0.0257 (11)0.0324 (13)0.0291 (12)−0.0035 (10)0.0065 (9)0.0062 (10)
C15E0.0220 (11)0.0317 (13)0.0287 (11)−0.0034 (9)−0.0039 (9)0.0039 (10)
C16E0.0228 (13)0.0286 (14)0.0329 (15)0.0006 (9)−0.0056 (11)−0.0008 (10)
C17E0.0258 (13)0.0383 (14)0.0447 (16)0.0067 (11)−0.0094 (11)0.0011 (13)
C18E0.0228 (10)0.0242 (11)0.0334 (12)−0.0002 (9)−0.0001 (10)0.0019 (10)
C19E0.0301 (12)0.0309 (14)0.0462 (15)−0.0039 (11)−0.0099 (11)−0.0027 (12)
C20E0.0286 (12)0.0362 (14)0.0313 (12)0.0050 (10)0.0002 (10)0.0054 (11)
N1F0.0175 (8)0.0324 (11)0.0261 (9)0.0002 (8)−0.0006 (7)−0.0015 (8)
N2F0.0185 (10)0.0221 (11)0.0314 (12)−0.0036 (7)−0.0014 (9)−0.0020 (8)
C1F0.0214 (10)0.0295 (12)0.0253 (11)0.0016 (9)0.0057 (9)−0.0057 (9)
C2F0.0257 (11)0.0364 (14)0.0329 (12)0.0013 (10)0.0035 (10)0.0006 (11)
C3F0.0336 (13)0.0338 (14)0.0503 (15)0.0059 (11)0.0109 (12)0.0055 (12)
C4F0.0322 (14)0.0311 (14)0.0660 (19)−0.0030 (12)0.0179 (13)−0.0052 (14)
C5F0.0234 (11)0.0376 (14)0.0486 (15)−0.0035 (10)0.0107 (11)−0.0170 (12)
C6F0.0226 (10)0.0391 (14)0.0289 (11)−0.0005 (10)0.0057 (9)−0.0074 (11)
C7F0.0297 (12)0.0585 (18)0.0333 (13)−0.0083 (12)−0.0058 (10)−0.0035 (12)
C8F0.0274 (12)0.0620 (18)0.0292 (12)−0.0051 (12)−0.0050 (10)0.0106 (12)
C9F0.0223 (13)0.0397 (15)0.0323 (15)−0.0026 (10)0.0002 (11)0.0115 (11)
C10F0.0224 (11)0.0425 (15)0.0549 (16)−0.0018 (11)−0.0008 (11)0.0195 (13)
C11F0.0302 (13)0.0257 (13)0.074 (2)0.0031 (10)0.0089 (13)0.0070 (13)
C12F0.0316 (13)0.0329 (14)0.0539 (17)−0.0013 (11)0.0083 (12)−0.0014 (13)
C13F0.0263 (11)0.0306 (13)0.0368 (13)−0.0019 (10)0.0015 (10)0.0011 (11)
C14F0.0214 (12)0.0316 (14)0.0241 (13)−0.0044 (9)0.0027 (10)0.0059 (9)
C15F0.0205 (10)0.0303 (12)0.0293 (11)0.0019 (9)−0.0006 (9)−0.0008 (10)
C16F0.0205 (12)0.0222 (13)0.0317 (15)−0.0012 (8)0.0004 (11)0.0001 (9)
C17F0.0249 (12)0.0359 (14)0.0408 (15)−0.0072 (11)−0.0031 (10)−0.0003 (13)
C18F0.0228 (10)0.0184 (11)0.0347 (12)−0.0014 (8)0.0013 (9)0.0016 (10)
C19F0.0285 (12)0.0348 (14)0.0322 (12)−0.0042 (10)0.0030 (10)−0.0069 (11)
C20F0.0274 (11)0.0316 (14)0.0433 (14)0.0022 (10)−0.0058 (11)0.0011 (11)
N1G0.0293 (10)0.0263 (11)0.0237 (10)0.0004 (8)0.0006 (8)0.0018 (8)
N2G0.0233 (10)0.0254 (10)0.0279 (11)−0.0062 (8)−0.0036 (9)0.0036 (9)
C1G0.0293 (12)0.0257 (13)0.0234 (11)−0.0037 (10)−0.0045 (10)−0.0001 (10)
C2G0.0257 (11)0.0343 (13)0.0272 (11)−0.0063 (10)−0.0020 (9)0.0016 (10)
C3G0.0286 (11)0.0430 (15)0.0345 (13)0.0049 (11)−0.0045 (10)0.0035 (11)
C4G0.0444 (14)0.0381 (15)0.0435 (14)0.0039 (12)−0.0038 (12)0.0150 (12)
C5G0.0371 (13)0.0410 (15)0.0358 (13)−0.0041 (11)0.0052 (11)0.0111 (11)
C6G0.0293 (11)0.0305 (13)0.0272 (11)−0.0065 (10)−0.0011 (9)−0.0013 (10)
C7G0.0291 (11)0.0332 (13)0.0289 (12)−0.0067 (10)0.0031 (10)0.0050 (10)
C8G0.0386 (13)0.0355 (14)0.0315 (12)−0.0062 (11)0.0088 (11)−0.0019 (11)
C9G0.0287 (13)0.0304 (14)0.0321 (14)−0.0014 (10)−0.0019 (12)0.0010 (10)
C10G0.0365 (13)0.0394 (15)0.0365 (13)0.0008 (11)−0.0003 (11)−0.0068 (12)
C11G0.0368 (13)0.0311 (14)0.0451 (15)0.0014 (11)−0.0083 (12)−0.0098 (12)
C12G0.0304 (13)0.0283 (14)0.0441 (15)−0.0061 (10)−0.0101 (12)0.0066 (12)
C13G0.0241 (11)0.0326 (13)0.0339 (13)−0.0035 (10)−0.0020 (10)0.0046 (11)
C14G0.0232 (14)0.0323 (15)0.0303 (15)−0.0031 (9)−0.0047 (11)0.0040 (10)
C15G0.0263 (11)0.0278 (12)0.0249 (11)0.0016 (9)−0.0002 (9)0.0028 (9)
C16G0.0222 (10)0.0221 (11)0.0262 (11)−0.0009 (9)0.0015 (9)0.0001 (9)
C17G0.0285 (11)0.0251 (12)0.0314 (12)−0.0041 (9)−0.0008 (10)0.0060 (10)
C18G0.0197 (10)0.0285 (12)0.0251 (11)0.0007 (10)−0.0007 (9)0.0014 (10)
C19G0.0357 (13)0.0215 (12)0.0439 (14)0.0018 (10)−0.0109 (11)0.0007 (11)
C20G0.0375 (14)0.0577 (19)0.0271 (12)−0.0180 (13)−0.0049 (11)0.0136 (13)
N1H0.0280 (10)0.0287 (11)0.0240 (10)−0.0024 (8)0.0014 (8)0.0000 (8)
N2H0.0245 (10)0.0238 (10)0.0245 (11)0.0056 (8)−0.0010 (8)−0.0026 (8)
C1H0.0251 (12)0.0262 (13)0.0230 (11)0.0027 (9)−0.0028 (9)0.0044 (10)
C2H0.0221 (10)0.0341 (13)0.0226 (10)0.0008 (9)−0.0041 (9)0.0041 (9)
C3H0.0321 (11)0.0316 (13)0.0283 (11)−0.0064 (10)−0.0078 (9)0.0083 (10)
C4H0.0434 (13)0.0216 (11)0.0346 (12)−0.0019 (10)−0.0086 (11)0.0052 (10)
C5H0.0370 (13)0.0299 (13)0.0318 (12)0.0081 (10)−0.0019 (10)−0.0027 (10)
C6H0.0259 (11)0.0312 (13)0.0295 (12)0.0037 (10)−0.0022 (9)0.0033 (10)
C7H0.0289 (12)0.0372 (14)0.0354 (13)0.0024 (10)0.0061 (10)−0.0061 (11)
C8H0.0382 (13)0.0358 (14)0.0329 (13)−0.0092 (11)0.0097 (11)−0.0022 (11)
C9H0.0294 (13)0.0331 (15)0.0286 (14)−0.0081 (10)0.0017 (11)−0.0025 (10)
C10H0.0427 (14)0.0404 (15)0.0313 (13)−0.0078 (12)0.0050 (12)0.0025 (11)
C11H0.0484 (16)0.0316 (14)0.0424 (15)−0.0027 (12)−0.0026 (12)0.0095 (12)
C12H0.0329 (14)0.0315 (14)0.0435 (16)0.0053 (11)0.0016 (12)−0.0005 (12)
C13H0.0287 (12)0.0329 (13)0.0296 (12)−0.0006 (10)−0.0005 (10)0.0003 (11)
C14H0.0234 (13)0.0251 (13)0.0274 (14)−0.0032 (9)−0.0017 (11)−0.0019 (9)
C15H0.0254 (10)0.0258 (12)0.0265 (11)−0.0034 (9)0.0009 (9)0.0011 (10)
C16H0.0230 (10)0.0211 (11)0.0249 (11)−0.0005 (8)0.0012 (9)−0.0008 (9)
C17H0.0287 (12)0.0298 (13)0.0349 (13)0.0062 (10)−0.0017 (10)−0.0074 (11)
C18H0.0164 (10)0.0292 (12)0.0292 (12)0.0007 (9)0.0018 (9)−0.0011 (11)
C19H0.0365 (12)0.0188 (11)0.0432 (14)−0.0034 (10)−0.0092 (11)0.0002 (11)
C20H0.0351 (13)0.061 (2)0.0275 (12)0.0180 (13)−0.0043 (11)−0.0120 (13)

Geometric parameters (Å, °)

O1A—C1A1.260 (3)C12F—H12B0.9500
O2A—C1A1.246 (3)C13F—C14F1.391 (4)
O3A—C4A1.308 (3)C13F—H13B0.9500
O3A—H3A0.8400C15F—C16F1.545 (4)
O4A—C4A1.219 (3)C15F—H15C0.9900
C1A—C2A1.506 (3)C15F—H15D0.9900
C2A—C3A1.330 (3)C16F—C18F1.509 (4)
C2A—H2AA0.9500C16F—C17F1.530 (3)
C3A—C4A1.501 (3)C16F—H16B1.0000
C3A—H3AA0.9500C17F—H17D0.9800
O1B—C1B1.280 (3)C17F—H17E0.9800
O2B—C1B1.241 (3)C17F—H17F0.9800
O3B—C4B1.299 (3)C18F—H18C0.9900
O3B—H3B0.8400C18F—H18D0.9900
O4B—C4B1.224 (3)C19F—H19D0.9800
C1B—C2B1.497 (3)C19F—H19E0.9800
C2B—C3B1.331 (3)C19F—H19F0.9800
C2B—H2BA0.9500C20F—H20D0.9800
C3B—C4B1.500 (3)C20F—H20E0.9800
C3B—H3BA0.9500C20F—H20F0.9800
O1C—C1C1.270 (3)N1G—C14G1.423 (3)
O2C—C1C1.238 (3)N1G—C1G1.426 (3)
O3C—C4C1.296 (3)N1G—C15G1.469 (3)
O3C—H3C0.8400N2G—C20G1.482 (3)
O4C—C4C1.226 (3)N2G—C19G1.485 (3)
C1C—C2C1.509 (3)N2G—C18G1.506 (3)
C2C—C3C1.325 (3)N2G—H2GB0.9300
C2C—H2CA0.9500C1G—C6G1.391 (4)
C3C—C4C1.498 (4)C1G—C2G1.394 (4)
C3C—H3CA0.9500C2G—C3G1.384 (4)
O1D—C1D1.302 (3)C2G—H2GA0.9500
O2D—C1D1.226 (3)C3G—C4G1.390 (4)
O3D—C4D1.272 (3)C3G—H3GA0.9500
O3D—H3D0.8400C4G—C5G1.385 (4)
O4D—C4D1.242 (3)C4G—H4GA0.9500
C1D—C2D1.490 (4)C5G—C6G1.393 (4)
C2D—C3D1.331 (3)C5G—H5GA0.9500
C2D—H2DA0.9500C6G—C7G1.503 (3)
C3D—C4D1.499 (3)C7G—C8G1.524 (4)
C3D—H3DA0.9500C7G—H7GA0.9900
N1E—C14E1.421 (3)C7G—H7GB0.9900
N1E—C1E1.436 (3)C8G—C9G1.523 (4)
N1E—C15E1.468 (3)C8G—H8GA0.9900
N2E—C20E1.484 (3)C8G—H8GB0.9900
N2E—C19E1.488 (3)C9G—C10G1.399 (4)
N2E—C18E1.510 (3)C9G—C14G1.413 (4)
N2E—H2EB0.9300C10G—C11G1.391 (4)
C1E—C2E1.390 (4)C10G—H10C0.9500
C1E—C6E1.402 (4)C11G—C12G1.383 (4)
C2E—C3E1.393 (4)C11G—H11C0.9500
C2E—H2EA0.9500C12G—C13G1.384 (4)
C3E—C4E1.377 (5)C12G—H12C0.9500
C3E—H3EA0.9500C13G—C14G1.409 (4)
C4E—C5E1.380 (5)C13G—H13C0.9500
C4E—H4EA0.9500C15G—C16G1.537 (3)
C5E—C6E1.394 (4)C15G—H15E0.9900
C5E—H5EA0.9500C15G—H15F0.9900
C6E—C7E1.490 (5)C16G—C18G1.522 (3)
C7E—C8E1.509 (5)C16G—C17G1.527 (3)
C7E—H7EA0.9900C16G—H16C1.0000
C7E—H7EB0.9900C17G—H17G0.9800
C8E—C9E1.529 (4)C17G—H17H0.9800
C8E—H8EA0.9900C17G—H17I0.9800
C8E—H8EB0.9900C18G—H18E0.9900
C9E—C10E1.395 (4)C18G—H18F0.9900
C9E—C14E1.406 (4)C19G—H19G0.9800
C10E—C11E1.382 (5)C19G—H19H0.9800
C10E—H10A0.9500C19G—H19I0.9800
C11E—C12E1.372 (5)C20G—H20G0.9800
C11E—H11A0.9500C20G—H20H0.9800
C12E—C13E1.386 (4)C20G—H20I0.9800
C12E—H12A0.9500N1H—C1H1.421 (3)
C13E—C14E1.404 (4)N1H—C14H1.429 (3)
C13E—H13A0.9500N1H—C15H1.470 (3)
C15E—C16E1.514 (4)N2H—C20H1.493 (3)
C15E—H15A0.9900N2H—C19H1.494 (3)
C15E—H15B0.9900N2H—C18H1.498 (3)
C16E—C18E1.525 (4)N2H—H2HB0.9300
C16E—C17E1.531 (4)C1H—C2H1.401 (3)
C16E—H16A1.0000C1H—C6H1.402 (4)
C17E—H17A0.9800C2H—C3H1.379 (4)
C17E—H17B0.9800C2H—H2HA0.9500
C17E—H17C0.9800C3H—C4H1.391 (4)
C18E—H18A0.9900C3H—H3HA0.9500
C18E—H18B0.9900C4H—C5H1.385 (4)
C19E—H19A0.9800C4H—H4HA0.9500
C19E—H19B0.9800C5H—C6H1.388 (4)
C19E—H19C0.9800C5H—H5HA0.9500
C20E—H20A0.9800C6H—C7H1.505 (3)
C20E—H20B0.9800C7H—C8H1.520 (4)
C20E—H20C0.9800C7H—H7HA0.9900
N1F—C14F1.427 (3)C7H—H7HB0.9900
N1F—C1F1.435 (3)C8H—C9H1.522 (4)
N1F—C15F1.465 (3)C8H—H8HA0.9900
N2F—C20F1.485 (3)C8H—H8HB0.9900
N2F—C19F1.488 (3)C9H—C10H1.395 (4)
N2F—C18F1.511 (3)C9H—C14H1.413 (4)
N2F—H2FB0.9300C10H—C11H1.384 (4)
C1F—C2F1.397 (4)C10H—H10D0.9500
C1F—C6F1.411 (3)C11H—C12H1.376 (4)
C2F—C3F1.388 (4)C11H—H11D0.9500
C2F—H2FA0.9500C12H—C13H1.380 (4)
C3F—C4F1.381 (4)C12H—H12D0.9500
C3F—H3FA0.9500C13H—C14H1.398 (4)
C4F—C5F1.377 (4)C13H—H13D0.9500
C4F—H4FA0.9500C15H—C16H1.534 (3)
C5F—C6F1.388 (4)C15H—H15G0.9900
C5F—H5FA0.9500C15H—H15H0.9900
C6F—C7F1.517 (4)C16H—C18H1.521 (3)
C7F—C8F1.515 (4)C16H—C17H1.532 (3)
C7F—H7FA0.9900C16H—H16D1.0000
C7F—H7FB0.9900C17H—H17J0.9800
C8F—C9F1.500 (4)C17H—H17K0.9800
C8F—H8FA0.9900C17H—H17L0.9800
C8F—H8FB0.9900C18H—H18G0.9900
C9F—C14F1.396 (4)C18H—H18H0.9900
C9F—C10F1.399 (4)C19H—H19J0.9800
C10F—C11F1.386 (4)C19H—H19K0.9800
C10F—H10B0.9500C19H—H19L0.9800
C11F—C12F1.384 (4)C20H—H20J0.9800
C11F—H11B0.9500C20H—H20K0.9800
C12F—C13F1.382 (4)C20H—H20L0.9800
C4A—O3A—H3A109.5C17F—C16F—H16B109.1
O2A—C1A—O1A123.8 (2)C15F—C16F—H16B109.1
O2A—C1A—C2A116.1 (2)C16F—C17F—H17D109.5
O1A—C1A—C2A120.0 (2)C16F—C17F—H17E109.5
C3A—C2A—C1A129.7 (2)H17D—C17F—H17E109.5
C3A—C2A—H2AA115.2C16F—C17F—H17F109.5
C1A—C2A—H2AA115.2H17D—C17F—H17F109.5
C2A—C3A—C4A130.0 (2)H17E—C17F—H17F109.5
C2A—C3A—H3AA115.0C16F—C18F—N2F115.35 (19)
C4A—C3A—H3AA115.0C16F—C18F—H18C108.4
O4A—C4A—O3A122.1 (2)N2F—C18F—H18C108.4
O4A—C4A—C3A118.6 (2)C16F—C18F—H18D108.4
O3A—C4A—C3A119.3 (2)N2F—C18F—H18D108.4
C4B—O3B—H3B109.5H18C—C18F—H18D107.5
O2B—C1B—O1B123.3 (2)N2F—C19F—H19D109.5
O2B—C1B—C2B116.8 (2)N2F—C19F—H19E109.5
O1B—C1B—C2B120.0 (2)H19D—C19F—H19E109.5
C3B—C2B—C1B129.6 (2)N2F—C19F—H19F109.5
C3B—C2B—H2BA115.2H19D—C19F—H19F109.5
C1B—C2B—H2BA115.2H19E—C19F—H19F109.5
C2B—C3B—C4B130.3 (2)N2F—C20F—H20D109.5
C2B—C3B—H3BA114.8N2F—C20F—H20E109.5
C4B—C3B—H3BA114.8H20D—C20F—H20E109.5
O4B—C4B—O3B121.9 (2)N2F—C20F—H20F109.5
O4B—C4B—C3B118.5 (2)H20D—C20F—H20F109.5
O3B—C4B—C3B119.7 (2)H20E—C20F—H20F109.5
C4C—O3C—H3C109.5C14G—N1G—C1G120.0 (2)
O2C—C1C—O1C123.3 (2)C14G—N1G—C15G118.9 (2)
O2C—C1C—C2C117.1 (2)C1G—N1G—C15G116.5 (2)
O1C—C1C—C2C119.7 (2)C20G—N2G—C19G110.5 (2)
C3C—C2C—C1C129.9 (2)C20G—N2G—C18G108.8 (2)
C3C—C2C—H2CA115.1C19G—N2G—C18G113.1 (2)
C1C—C2C—H2CA115.1C20G—N2G—H2GB108.1
C2C—C3C—C4C131.2 (2)C19G—N2G—H2GB108.1
C2C—C3C—H3CA114.4C18G—N2G—H2GB108.1
C4C—C3C—H3CA114.4C6G—C1G—C2G120.0 (2)
O4C—C4C—O3C121.9 (2)C6G—C1G—N1G118.8 (2)
O4C—C4C—C3C118.3 (2)C2G—C1G—N1G121.1 (2)
O3C—C4C—C3C119.8 (2)C3G—C2G—C1G120.8 (2)
C4D—O3D—H3D109.5C3G—C2G—H2GA119.6
O2D—C1D—O1D121.8 (3)C1G—C2G—H2GA119.6
O2D—C1D—C2D118.4 (2)C2G—C3G—C4G119.3 (2)
O1D—C1D—C2D119.8 (2)C2G—C3G—H3GA120.3
C3D—C2D—C1D131.3 (2)C4G—C3G—H3GA120.3
C3D—C2D—H2DA114.4C5G—C4G—C3G120.0 (3)
C1D—C2D—H2DA114.4C5G—C4G—H4GA120.0
C2D—C3D—C4D129.7 (2)C3G—C4G—H4GA120.0
C2D—C3D—H3DA115.1C4G—C5G—C6G121.1 (2)
C4D—C3D—H3DA115.1C4G—C5G—H5GA119.4
O4D—C4D—O3D122.8 (2)C6G—C5G—H5GA119.4
O4D—C4D—C3D117.0 (2)C1G—C6G—C5G118.8 (2)
O3D—C4D—C3D120.2 (2)C1G—C6G—C7G118.3 (2)
C14E—N1E—C1E117.2 (2)C5G—C6G—C7G122.9 (2)
C14E—N1E—C15E118.7 (2)C6G—C7G—C8G111.4 (2)
C1E—N1E—C15E116.2 (2)C6G—C7G—H7GA109.3
C20E—N2E—C19E110.8 (2)C8G—C7G—H7GA109.3
C20E—N2E—C18E109.06 (18)C6G—C7G—H7GB109.3
C19E—N2E—C18E112.6 (2)C8G—C7G—H7GB109.3
C20E—N2E—H2EB108.1H7GA—C7G—H7GB108.0
C19E—N2E—H2EB108.1C9G—C8G—C7G117.6 (2)
C18E—N2E—H2EB108.1C9G—C8G—H8GA107.9
C2E—C1E—C6E120.9 (3)C7G—C8G—H8GA107.9
C2E—C1E—N1E122.1 (2)C9G—C8G—H8GB107.9
C6E—C1E—N1E117.0 (3)C7G—C8G—H8GB107.9
C1E—C2E—C3E119.6 (3)H8GA—C8G—H8GB107.2
C1E—C2E—H2EA120.2C10G—C9G—C14G118.0 (3)
C3E—C2E—H2EA120.2C10G—C9G—C8G115.7 (3)
C4E—C3E—C2E120.1 (3)C14G—C9G—C8G126.3 (2)
C4E—C3E—H3EA120.0C11G—C10G—C9G123.1 (3)
C2E—C3E—H3EA120.0C11G—C10G—H10C118.5
C3E—C4E—C5E120.1 (3)C9G—C10G—H10C118.5
C3E—C4E—H4EA119.9C12G—C11G—C10G118.5 (3)
C5E—C4E—H4EA119.9C12G—C11G—H11C120.7
C4E—C5E—C6E121.4 (3)C10G—C11G—H11C120.7
C4E—C5E—H5EA119.3C11G—C12G—C13G120.1 (3)
C6E—C5E—H5EA119.3C11G—C12G—H12C120.0
C5E—C6E—C1E117.9 (3)C13G—C12G—H12C120.0
C5E—C6E—C7E123.0 (3)C12G—C13G—C14G121.9 (3)
C1E—C6E—C7E119.1 (3)C12G—C13G—H13C119.1
C6E—C7E—C8E113.3 (2)C14G—C13G—H13C119.1
C6E—C7E—H7EA108.9C13G—C14G—C9G118.5 (2)
C8E—C7E—H7EA108.9C13G—C14G—N1G119.4 (3)
C6E—C7E—H7EB108.9C9G—C14G—N1G122.0 (2)
C8E—C7E—H7EB108.9N1G—C15G—C16G110.87 (19)
H7EA—C7E—H7EB107.7N1G—C15G—H15E109.5
C7E—C8E—C9E118.9 (2)C16G—C15G—H15E109.5
C7E—C8E—H8EA107.6N1G—C15G—H15F109.5
C9E—C8E—H8EA107.6C16G—C15G—H15F109.5
C7E—C8E—H8EB107.6H15E—C15G—H15F108.1
C9E—C8E—H8EB107.6C18G—C16G—C17G112.0 (2)
H8EA—C8E—H8EB107.0C18G—C16G—C15G107.13 (18)
C10E—C9E—C14E118.3 (3)C17G—C16G—C15G111.55 (19)
C10E—C9E—C8E115.8 (3)C18G—C16G—H16C108.7
C14E—C9E—C8E125.9 (3)C17G—C16G—H16C108.7
C11E—C10E—C9E122.5 (3)C15G—C16G—H16C108.7
C11E—C10E—H10A118.8C16G—C17G—H17G109.5
C9E—C10E—H10A118.8C16G—C17G—H17H109.5
C12E—C11E—C10E119.1 (3)H17G—C17G—H17H109.5
C12E—C11E—H11A120.5C16G—C17G—H17I109.5
C10E—C11E—H11A120.5H17G—C17G—H17I109.5
C11E—C12E—C13E120.2 (3)H17H—C17G—H17I109.5
C11E—C12E—H12A119.9N2G—C18G—C16G113.87 (19)
C13E—C12E—H12A119.9N2G—C18G—H18E108.8
C12E—C13E—C14E121.2 (3)C16G—C18G—H18E108.8
C12E—C13E—H13A119.4N2G—C18G—H18F108.8
C14E—C13E—H13A119.4C16G—C18G—H18F108.8
C13E—C14E—C9E118.7 (3)H18E—C18G—H18F107.7
C13E—C14E—N1E119.8 (2)N2G—C19G—H19G109.5
C9E—C14E—N1E121.4 (2)N2G—C19G—H19H109.5
N1E—C15E—C16E111.4 (2)H19G—C19G—H19H109.5
N1E—C15E—H15A109.4N2G—C19G—H19I109.5
C16E—C15E—H15A109.4H19G—C19G—H19I109.5
N1E—C15E—H15B109.4H19H—C19G—H19I109.5
C16E—C15E—H15B109.4N2G—C20G—H20G109.5
H15A—C15E—H15B108.0N2G—C20G—H20H109.5
C15E—C16E—C18E109.2 (2)H20G—C20G—H20H109.5
C15E—C16E—C17E109.8 (2)N2G—C20G—H20I109.5
C18E—C16E—C17E110.6 (2)H20G—C20G—H20I109.5
C15E—C16E—H16A109.1H20H—C20G—H20I109.5
C18E—C16E—H16A109.1C1H—N1H—C14H120.3 (2)
C17E—C16E—H16A109.1C1H—N1H—C15H115.8 (2)
C16E—C17E—H17A109.5C14H—N1H—C15H118.7 (2)
C16E—C17E—H17B109.5C20H—N2H—C19H110.8 (2)
H17A—C17E—H17B109.5C20H—N2H—C18H109.3 (2)
C16E—C17E—H17C109.5C19H—N2H—C18H112.5 (2)
H17A—C17E—H17C109.5C20H—N2H—H2HB108.0
H17B—C17E—H17C109.5C19H—N2H—H2HB108.0
N2E—C18E—C16E115.77 (19)C18H—N2H—H2HB108.0
N2E—C18E—H18A108.3C2H—C1H—C6H119.1 (2)
C16E—C18E—H18A108.3C2H—C1H—N1H121.2 (2)
N2E—C18E—H18B108.3C6H—C1H—N1H119.6 (2)
C16E—C18E—H18B108.3C3H—C2H—C1H121.2 (2)
H18A—C18E—H18B107.4C3H—C2H—H2HA119.4
N2E—C19E—H19A109.5C1H—C2H—H2HA119.4
N2E—C19E—H19B109.5C2H—C3H—C4H119.6 (2)
H19A—C19E—H19B109.5C2H—C3H—H3HA120.2
N2E—C19E—H19C109.5C4H—C3H—H3HA120.2
H19A—C19E—H19C109.5C5H—C4H—C3H119.4 (2)
H19B—C19E—H19C109.5C5H—C4H—H4HA120.3
N2E—C20E—H20A109.5C3H—C4H—H4HA120.3
N2E—C20E—H20B109.5C4H—C5H—C6H121.8 (2)
H20A—C20E—H20B109.5C4H—C5H—H5HA119.1
N2E—C20E—H20C109.5C6H—C5H—H5HA119.1
H20A—C20E—H20C109.5C5H—C6H—C1H118.7 (2)
H20B—C20E—H20C109.5C5H—C6H—C7H123.6 (2)
C14F—N1F—C1F117.79 (19)C1H—C6H—C7H117.6 (2)
C14F—N1F—C15F116.4 (2)C6H—C7H—C8H112.3 (2)
C1F—N1F—C15F117.94 (19)C6H—C7H—H7HA109.1
C20F—N2F—C19F110.8 (2)C8H—C7H—H7HA109.1
C20F—N2F—C18F111.8 (2)C6H—C7H—H7HB109.1
C19F—N2F—C18F109.14 (18)C8H—C7H—H7HB109.1
C20F—N2F—H2FB108.3H7HA—C7H—H7HB107.9
C19F—N2F—H2FB108.3C7H—C8H—C9H118.4 (2)
C18F—N2F—H2FB108.3C7H—C8H—H8HA107.7
C2F—C1F—C6F119.0 (2)C9H—C8H—H8HA107.7
C2F—C1F—N1F119.6 (2)C7H—C8H—H8HB107.7
C6F—C1F—N1F121.3 (2)C9H—C8H—H8HB107.7
C3F—C2F—C1F121.5 (2)H8HA—C8H—H8HB107.1
C3F—C2F—H2FA119.3C10H—C9H—C14H117.4 (3)
C1F—C2F—H2FA119.3C10H—C9H—C8H116.2 (3)
C4F—C3F—C2F119.7 (3)C14H—C9H—C8H126.4 (2)
C4F—C3F—H3FA120.2C11H—C10H—C9H123.2 (3)
C2F—C3F—H3FA120.2C11H—C10H—H10D118.4
C5F—C4F—C3F118.8 (3)C9H—C10H—H10D118.4
C5F—C4F—H4FA120.6C12H—C11H—C10H118.7 (3)
C3F—C4F—H4FA120.6C12H—C11H—H11D120.7
C4F—C5F—C6F123.4 (3)C10H—C11H—H11D120.7
C4F—C5F—H5FA118.3C11H—C12H—C13H120.0 (3)
C6F—C5F—H5FA118.3C11H—C12H—H12D120.0
C5F—C6F—C1F117.5 (2)C13H—C12H—H12D120.0
C5F—C6F—C7F116.2 (2)C12H—C13H—C14H121.8 (3)
C1F—C6F—C7F126.2 (2)C12H—C13H—H13D119.1
C8F—C7F—C6F118.5 (2)C14H—C13H—H13D119.1
C8F—C7F—H7FA107.7C13H—C14H—C9H118.8 (2)
C6F—C7F—H7FA107.7C13H—C14H—N1H119.6 (3)
C8F—C7F—H7FB107.7C9H—C14H—N1H121.5 (2)
C6F—C7F—H7FB107.7N1H—C15H—C16H111.01 (18)
H7FA—C7F—H7FB107.1N1H—C15H—H15G109.4
C9F—C8F—C7F111.6 (2)C16H—C15H—H15G109.4
C9F—C8F—H8FA109.3N1H—C15H—H15H109.4
C7F—C8F—H8FA109.3C16H—C15H—H15H109.4
C9F—C8F—H8FB109.3H15G—C15H—H15H108.0
C7F—C8F—H8FB109.3C18H—C16H—C17H112.0 (2)
H8FA—C8F—H8FB108.0C18H—C16H—C15H107.05 (18)
C14F—C9F—C10F118.5 (3)C17H—C16H—C15H110.61 (19)
C14F—C9F—C8F118.9 (2)C18H—C16H—H16D109.0
C10F—C9F—C8F122.6 (3)C17H—C16H—H16D109.0
C11F—C10F—C9F121.5 (3)C15H—C16H—H16D109.0
C11F—C10F—H10B119.3C16H—C17H—H17J109.5
C9F—C10F—H10B119.3C16H—C17H—H17K109.5
C12F—C11F—C10F119.5 (3)H17J—C17H—H17K109.5
C12F—C11F—H11B120.3C16H—C17H—H17L109.5
C10F—C11F—H11B120.3H17J—C17H—H17L109.5
C13F—C12F—C11F119.7 (3)H17K—C17H—H17L109.5
C13F—C12F—H12B120.2N2H—C18H—C16H114.64 (18)
C11F—C12F—H12B120.2N2H—C18H—H18G108.6
C12F—C13F—C14F121.3 (3)C16H—C18H—H18G108.6
C12F—C13F—H13B119.3N2H—C18H—H18H108.6
C14F—C13F—H13B119.3C16H—C18H—H18H108.6
C13F—C14F—C9F119.5 (3)H18G—C18H—H18H107.6
C13F—C14F—N1F122.6 (2)N2H—C19H—H19J109.5
C9F—C14F—N1F117.9 (2)N2H—C19H—H19K109.5
N1F—C15F—C16F110.8 (2)H19J—C19H—H19K109.5
N1F—C15F—H15C109.5N2H—C19H—H19L109.5
C16F—C15F—H15C109.5H19J—C19H—H19L109.5
N1F—C15F—H15D109.5H19K—C19H—H19L109.5
C16F—C15F—H15D109.5N2H—C20H—H20J109.5
H15C—C15F—H15D108.1N2H—C20H—H20K109.5
C18F—C16F—C17F112.4 (2)H20J—C20H—H20K109.5
C18F—C16F—C15F108.10 (19)N2H—C20H—H20L109.5
C17F—C16F—C15F109.1 (2)H20J—C20H—H20L109.5
C18F—C16F—H16B109.1H20K—C20H—H20L109.5
O2A—C1A—C2A—C3A−163.1 (3)C1F—N1F—C14F—C9F71.6 (3)
O1A—C1A—C2A—C3A16.6 (4)C15F—N1F—C14F—C9F−139.7 (2)
C1A—C2A—C3A—C4A0.3 (4)C14F—N1F—C15F—C16F67.3 (3)
C2A—C3A—C4A—O4A162.5 (3)C1F—N1F—C15F—C16F−144.1 (2)
C2A—C3A—C4A—O3A−18.1 (4)N1F—C15F—C16F—C18F71.8 (3)
O2B—C1B—C2B—C3B−162.4 (3)N1F—C15F—C16F—C17F−165.6 (2)
O1B—C1B—C2B—C3B17.1 (4)C17F—C16F—C18F—N2F73.5 (3)
C1B—C2B—C3B—C4B−0.8 (5)C15F—C16F—C18F—N2F−166.03 (19)
C2B—C3B—C4B—O4B163.4 (3)C20F—N2F—C18F—C16F76.0 (3)
C2B—C3B—C4B—O3B−16.5 (4)C19F—N2F—C18F—C16F−161.0 (2)
O2C—C1C—C2C—C3C−173.9 (3)C14G—N1G—C1G—C6G−72.0 (3)
O1C—C1C—C2C—C3C5.0 (4)C15G—N1G—C1G—C6G132.2 (2)
C1C—C2C—C3C—C4C−1.0 (5)C14G—N1G—C1G—C2G110.8 (3)
C2C—C3C—C4C—O4C177.9 (3)C15G—N1G—C1G—C2G−45.0 (3)
C2C—C3C—C4C—O3C−2.6 (4)C6G—C1G—C2G—C3G−2.5 (4)
O2D—C1D—C2D—C3D177.3 (3)N1G—C1G—C2G—C3G174.6 (2)
O1D—C1D—C2D—C3D−2.7 (4)C1G—C2G—C3G—C4G2.7 (4)
C1D—C2D—C3D—C4D−2.0 (5)C2G—C3G—C4G—C5G−1.4 (4)
C2D—C3D—C4D—O4D−172.6 (3)C3G—C4G—C5G—C6G−0.1 (4)
C2D—C3D—C4D—O3D6.8 (4)C2G—C1G—C6G—C5G1.0 (4)
C14E—N1E—C1E—C2E−107.9 (3)N1G—C1G—C6G—C5G−176.2 (2)
C15E—N1E—C1E—C2E40.9 (3)C2G—C1G—C6G—C7G−177.2 (2)
C14E—N1E—C1E—C6E72.4 (3)N1G—C1G—C6G—C7G5.6 (3)
C15E—N1E—C1E—C6E−138.8 (2)C4G—C5G—C6G—C1G0.2 (4)
C6E—C1E—C2E—C3E0.7 (4)C4G—C5G—C6G—C7G178.4 (3)
N1E—C1E—C2E—C3E−179.0 (2)C1G—C6G—C7G—C8G67.8 (3)
C1E—C2E—C3E—C4E−1.3 (4)C5G—C6G—C7G—C8G−110.3 (3)
C2E—C3E—C4E—C5E1.0 (4)C6G—C7G—C8G—C9G−65.4 (3)
C3E—C4E—C5E—C6E0.0 (4)C7G—C8G—C9G—C10G−166.5 (3)
C4E—C5E—C6E—C1E−0.6 (4)C7G—C8G—C9G—C14G10.3 (4)
C4E—C5E—C6E—C7E177.6 (3)C14G—C9G—C10G—C11G0.4 (4)
C2E—C1E—C6E—C5E0.3 (4)C8G—C9G—C10G—C11G177.5 (3)
N1E—C1E—C6E—C5E180.0 (2)C9G—C10G—C11G—C12G−1.0 (4)
C2E—C1E—C6E—C7E−178.0 (2)C10G—C11G—C12G—C13G0.5 (4)
N1E—C1E—C6E—C7E1.7 (4)C11G—C12G—C13G—C14G0.5 (4)
C5E—C6E—C7E—C8E111.5 (3)C12G—C13G—C14G—C9G−1.1 (4)
C1E—C6E—C7E—C8E−70.3 (3)C12G—C13G—C14G—N1G−179.8 (2)
C6E—C7E—C8E—C9E57.2 (4)C10G—C9G—C14G—C13G0.7 (4)
C7E—C8E—C9E—C10E174.6 (2)C8G—C9G—C14G—C13G−176.1 (3)
C7E—C8E—C9E—C14E−5.0 (4)C10G—C9G—C14G—N1G179.3 (2)
C14E—C9E—C10E—C11E−0.8 (4)C8G—C9G—C14G—N1G2.5 (4)
C8E—C9E—C10E—C11E179.5 (3)C1G—N1G—C14G—C13G−132.7 (3)
C9E—C10E—C11E—C12E−1.0 (4)C15G—N1G—C14G—C13G22.6 (4)
C10E—C11E—C12E—C13E0.9 (5)C1G—N1G—C14G—C9G48.7 (4)
C11E—C12E—C13E—C14E1.0 (4)C15G—N1G—C14G—C9G−156.0 (2)
C12E—C13E—C14E—C9E−2.8 (4)C14G—N1G—C15G—C16G70.4 (3)
C12E—C13E—C14E—N1E174.9 (2)C1G—N1G—C15G—C16G−133.5 (2)
C10E—C9E—C14E—C13E2.6 (3)N1G—C15G—C16G—C18G−163.6 (2)
C8E—C9E—C14E—C13E−177.8 (2)N1G—C15G—C16G—C17G73.5 (3)
C10E—C9E—C14E—N1E−174.9 (2)C20G—N2G—C18G—C16G−173.2 (2)
C8E—C9E—C14E—N1E4.6 (4)C19G—N2G—C18G—C16G−50.1 (3)
C1E—N1E—C14E—C13E121.5 (3)C17G—C16G—C18G—N2G−60.5 (3)
C15E—N1E—C14E—C13E−26.5 (3)C15G—C16G—C18G—N2G176.9 (2)
C1E—N1E—C14E—C9E−60.9 (3)C14H—N1H—C1H—C2H111.1 (3)
C15E—N1E—C14E—C9E151.0 (2)C15H—N1H—C1H—C2H−43.2 (3)
C14E—N1E—C15E—C16E−146.8 (2)C14H—N1H—C1H—C6H−73.4 (3)
C1E—N1E—C15E—C16E64.9 (3)C15H—N1H—C1H—C6H132.3 (2)
N1E—C15E—C16E—C18E69.9 (3)C6H—C1H—C2H—C3H−3.4 (3)
N1E—C15E—C16E—C17E−168.7 (2)N1H—C1H—C2H—C3H172.1 (2)
C20E—N2E—C18E—C16E−160.2 (2)C1H—C2H—C3H—C4H2.0 (3)
C19E—N2E—C18E—C16E76.4 (3)C2H—C3H—C4H—C5H0.8 (3)
C15E—C16E—C18E—N2E−165.9 (2)C3H—C4H—C5H—C6H−2.2 (4)
C17E—C16E—C18E—N2E73.2 (3)C4H—C5H—C6H—C1H0.7 (4)
C14F—N1F—C1F—C2F123.3 (2)C4H—C5H—C6H—C7H178.4 (2)
C15F—N1F—C1F—C2F−24.8 (3)C2H—C1H—C6H—C5H2.1 (4)
C14F—N1F—C1F—C6F−59.2 (3)N1H—C1H—C6H—C5H−173.6 (2)
C15F—N1F—C1F—C6F152.6 (2)C2H—C1H—C6H—C7H−175.8 (2)
C6F—C1F—C2F—C3F−3.5 (4)N1H—C1H—C6H—C7H8.6 (3)
N1F—C1F—C2F—C3F173.9 (2)C5H—C6H—C7H—C8H−112.9 (3)
C1F—C2F—C3F—C4F0.2 (4)C1H—C6H—C7H—C8H64.8 (3)
C2F—C3F—C4F—C5F2.1 (4)C6H—C7H—C8H—C9H−65.2 (3)
C3F—C4F—C5F—C6F−1.1 (4)C7H—C8H—C9H—C10H−166.9 (3)
C4F—C5F—C6F—C1F−2.1 (4)C7H—C8H—C9H—C14H11.0 (4)
C4F—C5F—C6F—C7F177.2 (2)C14H—C9H—C10H—C11H−1.1 (4)
C2F—C1F—C6F—C5F4.4 (3)C8H—C9H—C10H—C11H177.0 (3)
N1F—C1F—C6F—C5F−173.1 (2)C9H—C10H—C11H—C12H−0.2 (5)
C2F—C1F—C6F—C7F−174.9 (2)C10H—C11H—C12H—C13H0.8 (4)
N1F—C1F—C6F—C7F7.7 (4)C11H—C12H—C13H—C14H−0.1 (4)
C5F—C6F—C7F—C8F168.2 (2)C12H—C13H—C14H—C9H−1.2 (4)
C1F—C6F—C7F—C8F−12.5 (4)C12H—C13H—C14H—N1H−179.7 (3)
C6F—C7F—C8F—C9F62.7 (3)C10H—C9H—C14H—C13H1.7 (4)
C7F—C8F—C9F—C14F−70.6 (3)C8H—C9H—C14H—C13H−176.1 (3)
C7F—C8F—C9F—C10F108.7 (3)C10H—C9H—C14H—N1H−179.8 (2)
C14F—C9F—C10F—C11F−1.8 (4)C8H—C9H—C14H—N1H2.4 (4)
C8F—C9F—C10F—C11F178.9 (2)C1H—N1H—C14H—C13H−133.3 (3)
C9F—C10F—C11F—C12F0.0 (4)C15H—N1H—C14H—C13H20.3 (3)
C10F—C11F—C12F—C13F1.3 (4)C1H—N1H—C14H—C9H48.2 (3)
C11F—C12F—C13F—C14F−0.9 (4)C15H—N1H—C14H—C9H−158.2 (2)
C12F—C13F—C14F—C9F−0.9 (4)C1H—N1H—C15H—C16H−134.1 (2)
C12F—C13F—C14F—N1F−179.6 (2)C14H—N1H—C15H—C16H71.2 (3)
C10F—C9F—C14F—C13F2.2 (4)N1H—C15H—C16H—C18H−165.0 (2)
C8F—C9F—C14F—C13F−178.4 (2)N1H—C15H—C16H—C17H72.6 (2)
C10F—C9F—C14F—N1F−179.0 (2)C20H—N2H—C18H—C16H−172.8 (2)
C8F—C9F—C14F—N1F0.3 (4)C19H—N2H—C18H—C16H−49.3 (3)
C1F—N1F—C14F—C13F−109.6 (3)C17H—C16H—C18H—N2H−59.8 (3)
C15F—N1F—C14F—C13F39.0 (3)C15H—C16H—C18H—N2H178.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3A—H3A···O1A0.841.632.437 (2)161
O3B—H3B···O1B0.841.612.437 (2)167
O3C—H3C···O1C0.841.582.417 (3)177
O3D—H3D···O1D0.841.582.422 (3)178
N2E—H2EB···O2A0.931.862.736 (3)156
N2F—H2FB···O2B0.931.862.737 (3)156
N2G—H2GB···O2C0.931.872.760 (3)158
N2H—H2HB···O4D0.931.872.751 (3)158
N2H—H2HB···O3D0.932.633.312 (3)131
C17E—H17C···O2A0.982.633.560 (4)159
C18E—H18B···O2Di0.992.283.271 (3)174
C18F—H18C···O4Cii0.992.313.293 (3)174
C18G—H18E···O2B0.992.423.404 (3)171
C18G—H18F···O3Ciii0.992.543.453 (3)154
C18G—H18F···O4Ciii0.992.533.432 (3)152
C18H—H18G···O2A0.992.423.402 (3)173
C18H—H18H···O1Div0.992.553.473 (3)155
C18H—H18H···O2Div0.992.533.435 (3)152
C19E—H19A···O4D0.982.623.198 (3)118
C19F—H19E···O4Biv0.982.543.464 (3)158
C19G—H19I···O4Bv0.982.533.476 (3)163
C19H—H19K···O4Aii0.982.563.516 (3)164
C20E—H20A···O4Avi0.982.563.488 (3)159
C20G—H20H···O4Ciii0.982.603.479 (3)149
C20H—H20K···O2Div0.982.633.497 (3)148

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x−1/2, −y+1/2, z; (iii) x−1/2, −y−1/2, z; (iv) x+1/2, −y+1/2, z; (v) x+1/2, −y−1/2, z; (vi) x−1/2, −y+3/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2715).

References

  • Al-Badr, A. A. (1983). Anal. Prof. Drug Subs.12, 683–712.
  • Al-Badr, A. A. & Ibrahim, S. E. (1979). Spectrosc. Lett.12, 419–426
  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Biederman, J., Baldessarini, R., Wright, V., Knee, D. & Harmatz, J. (1989). J. Am. Acad. Child Adolesc. Psychiatry, 28, 777–784. [PubMed]
  • Bindya, S., Wong, W.-T., Ashok, M. A., Yathirajan, H. S. & Rathore, R. S. (2007). Acta Cryst. C63, o546–o548. [PubMed]
  • Broquet, K. (1999). South Med. J.92, 846–856. [PubMed]
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Harrison, W. T. A., Bindya, S., Ashok, M. A., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3143.
  • Harrison, W. T. A., Swamy, M. T., Nagaraja, P., Yathirajan, H. S. & Narayana, B. (2007). Acta Cryst. E63, o3892.
  • Jones, P. G., Kennard, O. & Horn, A. S. (1978). Acta Cryst. B34, 2027–2030.
  • Kamel, L. T., El Essawi, M., Wartchow, R. & Berthold, H. J. (2001). Z. Kristallogr. New Cryst. Struct.216, 359–360.
  • Lapierre, Y. D. (1989). Drugs, 38, 17–24. [PubMed]
  • Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED). Oxford Diffraction Ltd, Abingdon, England.
  • Portalone, G., Colapietro, M., Bindya, S., Ashok, M. A. & Yathirajan, H. S. (2007). Acta Cryst. E63, o746–o747.
  • Post, M. L., Kennard, O. & Horn, A. S. (1975). Acta Cryst. B31, 1008–1013.
  • Schmidt, J. R. & Polik, W. F. (2007). WebMO Pro. WebMO, LLC, Holland, MI, USA, available from http://www.webmo.net.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Somashekar, B. S., Nagana Gowda, G. A., Ramesha, A. R. & Khetrapal, C. L. (2004). Magn. Res. Chem.43, 166–170. [PubMed]
  • Swamy, M. T., Ashok, M. A., Yathirajan, H. S., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o4919.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography