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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2065–o2066.
Published online 2009 August 8. doi:  10.1107/S1600536809029833
PMCID: PMC2969866

2-((E)-{2-[(E)-2,3-Dihydroxy­benzyl­ideneamino]-5-methyl­phen­yl}iminiometh­yl)-6-hydroxy­phenolate

Abstract

The asymmetric unit of the title Schiff base compound, C21H18N2O4, consists of four independent zwitterions (A, B, C and D) with similar conformations. In each independent mol­ecule, the methyl group is disordered over two positions; the occupancies of the two positions are 0.819 (5) and 0.181 (5) in mol­ecule A, 0.912 (5) and 0.088 (5) in B, 0.734 (5) and 0.266 (5) in C, and 0.940 (6) and 0.060 (6) in D. The dihydroxy­phenyl and the hydroxy­phenolate rings in mol­ecule A form dihedral angles of 17.36 (12) and 13.30 (12)°, respectively, with the central benzene ring, whereas the respective angles for mol­ecules B, C and D are 30.22 (11)/7.46 (11), 35.26 (12)/11.01 (12) and 39.89 (12)/4.29 (12)°. In all independent mol­ecules, intra­molecular N—H(...)O and O—H(...)N hydrogen bonds generate S(6) ring motifs. The four independent mol­ecules are linked into two pairs, viz. AB and CD, by inter­molecular O—H(...)O hydrogen bonds. These pairs are linked into a two-dimensional network parallel to the ab plane by C—H(...)O hydrogen bonds. In addition, C—H(...)π and π–π [centroid–centroid distance = 3.5153 (14)–3.7810 (15) Å] inter­actions stabilize the crystal structure.

Related literature

For the biological applications of Schiff base derivatives, see: Dao et al. (2000 [triangle]); Eltayeb & Ahmed (2005a [triangle],b [triangle]); Karthikeyan et al. (2006 [triangle]); Sriram et al. (2006 [triangle]). For related structures, see: Eltayeb et al. (2007a [triangle],b [triangle], 2008 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2065-scheme1.jpg

Experimental

Crystal data

  • C21H18N2O4
  • M r = 362.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2065-efi1.jpg
  • a = 17.0634 (2) Å
  • b = 21.3455 (2) Å
  • c = 20.0291 (2) Å
  • β = 99.982 (1)°
  • V = 7184.70 (13) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.29 × 0.19 × 0.17 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.920, T max = 0.984
  • 67041 measured reflections
  • 12647 independent reflections
  • 8172 reflections with I > 2σ(I)
  • R int = 0.069

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.115
  • S = 1.03
  • 12647 reflections
  • 1075 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029833/ci2856sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029833/ci2856Isup2.hkl

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

Acknowledgments

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia (USM) for the E-Science Fund and RU research grants (Nos. PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120). The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. HKF and CSY thank USM for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). CSY thanks the Malaysian Government and USM for the award of the post of Research Officer under the Science Fund (grant No. 305/PFIZIK/613312).

supplementary crystallographic information

Comment

Schiff bases have received much attention because of their potential applications with some of these compounds exhibiting various pharmacological activities, as noted by their anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). Previously, we have reported the crystal structures of 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]bis(5-methylphenol) (Eltayeb et al., 2007a) and 6,6'-dimethyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol (Eltayeb et al., 2007b). In this paper, we report the crystal structure of the title compound, obtained by the reaction of 4-methyl-1,2-phenylenediamine and 2,3-dihydroxybenzaldehyde.

The asymmetric unit of title compound consists of four crystallographically independent zwitterions A, B, C and D with almost similar conformations (Fig. 1 and Fig. 2). Each zwitterion is formed by the transfer one of the ortho-hydroxyl proton onto the adjacent imine unit resulting in the formation of iminium and hydroxyphenolate groups, with corresponding changes in the C20—O3, C14—N2 and C14—C15 bond lengths. These bonds are comparable to those in the related structure (Eltayeb et al., 2008). The dihydroxyphenyl ring [C1–C6] and the hydroxyphenolate ring [C15–C20] in molecule A form dihedral angles of 17.36 (12) and 13.30 (12)°, respectively, with the benzene ring (C8–C13) whereas these angles for molecules B, C and D are 30.22 (11)/7.46 (11)°, 35.26 (12)/11.01 (12)° and 39.89 (12)/4.29 (12)°, respectively.

In each independent molecule, each intramolecular N—H···O and O—H···N hydrogen bonds (Table 1) generate an S(6) ring motif (Bernstein et al., 1995). The four independent molecules are linked into two pairs, A/B and C/D via intermolecular O—H···O hydrogen bonds (Fig. 2 and Table 1). Intermolecular C—H···O interactions link these pairs of molecules into two-dimensional networks parallel to ab plane (Fig. 3). In addition, C—H···π (Table 1) and π–π interactions [Cg6···Cg8 = 3.5534 (14) Å, Cg3···Cg11iv = 3.5153 (14) Å, Cg7···Cg9iv = 3.7810 (15) Å, Cg1···Cg5iv = 3.7581 (15) Å and Cg4···Cg10iv = 3.7518 (15) Å, where Cg1, Cg3, Cg4, Cg5, Cg6, Cg7, Cg8, Cg9, Cg10 and Cg11 are centroids of C15A–C20A, C8B–C13B, C15B–C20B, C8C–C13C, C1D–C6D, C8A–C13A, C1C–C6C, C15C–C20C, C8D–C13D, C15D–C20D benzene rings, respectively] stabilize the crystal structure.

Experimental

A solution of 4-methyl-1,2-phenylenediamine (0.244 g, 2 mmol) in ethanol (20 ml) was added into 2,3-dihydroxybenzaldehyde (0.552 g, 4 mmol). The mixture was refluxed with stirring for 30 min. The resultant red solution was filtered. Red crystals suitable for X-ray analysis were formed after a few days of slow evaporation of the solvent at room temperature.

Refinement

All O and N bound H atoms were located in a difference Fourier map and refined freely. The rest of the H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 or 0.96 Å and Uiso(H) = 1.2-1.5(methyl)Ueq(C). The rotating group model was applied for the methyl groups. The methyl group in each independent molecule is disordered over two positions, with refined site-occupancies of 0.819 (5) and 0.181 (5) for molecule A, 0.912 (5) and 0.088 (5) for B, 0.734 (5) and 0.266 (5) for C, and 0.940 (6) and 0.060 (6) for D. Atoms C21F and C21H were refined isotropically.

Figures

Fig. 1.
Molecule A of the title compound, with atom labels and 50% probability ellipsoids for non-H atoms. The other three independent molecules are labelled similarly. Intramolecular hydrogen bonds are shown as dashed lines. Both disorder components are shown. ...
Fig. 2.
The asymmetric unit of the title compound, showing four independent molecules. Displacement ellipsoids are drawn at the 20% probability level. For clarity, only O and N atoms are labelled. Intermolecular hydrogen bonds are shown as dashed lines.
Fig. 3.
The crystal packing of the title compound, viewed down the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

C21H18N2O4F(000) = 3040
Mr = 362.37Dx = 1.340 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9276 reflections
a = 17.0634 (2) Åθ = 2.2–29.6°
b = 21.3455 (2) ŵ = 0.09 mm1
c = 20.0291 (2) ÅT = 100 K
β = 99.982 (1)°Block, red
V = 7184.70 (13) Å30.29 × 0.19 × 0.17 mm
Z = 16

Data collection

Bruker SMART APEXII CCD area-detector diffractometer12647 independent reflections
Radiation source: fine-focus sealed tube8172 reflections with I > 2σ(I)
graphiteRint = 0.069
[var phi] and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −20→20
Tmin = 0.920, Tmax = 0.984k = −25→25
67041 measured reflectionsl = −23→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0429P)2 + 2.6321P] where P = (Fo2 + 2Fc2)/3
12647 reflections(Δ/σ)max = 0.001
1075 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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*/UeqOcc. (<1)
O1A1.19315 (10)0.46141 (9)0.86061 (9)0.0364 (5)
O2A1.03690 (10)0.47712 (8)0.86453 (9)0.0331 (4)
O3A0.91941 (9)0.51191 (9)0.75558 (9)0.0397 (5)
O4A0.97187 (13)0.53499 (12)0.63763 (11)0.0620 (7)
N1A0.91419 (11)0.45158 (9)0.92792 (10)0.0303 (5)
N2A0.80118 (13)0.48196 (10)0.81813 (12)0.0327 (5)
C1A1.08033 (13)0.44352 (11)0.91497 (12)0.0259 (5)
C2A1.16102 (13)0.43568 (12)0.91227 (12)0.0286 (6)
C3A1.20934 (14)0.40307 (12)0.96296 (12)0.0348 (6)
H3AA1.26300.39800.96100.042*
C4A1.17861 (15)0.37790 (14)1.01666 (13)0.0420 (7)
H4AA1.21160.35611.05060.050*
C5A1.09910 (14)0.38517 (13)1.01976 (13)0.0391 (7)
H5AA1.07870.36851.05610.047*
C6A1.04886 (13)0.41752 (11)0.96865 (12)0.0292 (6)
C7A0.96505 (14)0.42262 (12)0.97218 (13)0.0325 (6)
H7AA0.94690.40391.00860.039*
C8A0.83324 (14)0.45305 (11)0.93647 (14)0.0319 (6)
C9A0.80711 (15)0.44014 (12)0.99758 (14)0.0368 (6)
H9AA0.84430.43121.03610.044*
C10A0.72750 (15)0.44047 (12)1.00179 (15)0.0375 (7)
H10A0.71170.43101.04280.045*0.819 (5)
C11A0.67088 (15)0.45459 (11)0.94612 (15)0.0374 (7)
H11A0.61710.45450.94920.045*0.181 (5)
C12A0.69529 (14)0.46899 (11)0.88544 (15)0.0373 (7)
H12A0.65760.47950.84780.045*
C13A0.77596 (14)0.46789 (11)0.88016 (14)0.0330 (6)
C14A0.75666 (14)0.48370 (11)0.75795 (14)0.0338 (6)
H14A0.70290.47420.75450.041*
C15A0.78507 (14)0.49897 (11)0.69828 (13)0.0323 (6)
C16A0.73153 (16)0.50164 (12)0.63598 (15)0.0416 (7)
H16A0.67780.49340.63510.050*
C17A0.75728 (16)0.51593 (13)0.57788 (15)0.0457 (7)
H17A0.72110.51820.53750.055*
C18A0.83918 (17)0.52746 (13)0.57792 (14)0.0458 (7)
H18A0.85660.53690.53760.055*
C19A0.89239 (16)0.52477 (13)0.63700 (14)0.0418 (7)
C20A0.86793 (15)0.51179 (12)0.70029 (13)0.0351 (6)
C21A0.58355 (16)0.45353 (14)0.95249 (15)0.0316 (9)0.819 (5)
H21A0.57880.45500.99950.047*0.819 (5)
H21B0.55940.41580.93250.047*0.819 (5)
H21C0.55720.48920.92950.047*0.819 (5)
C21E0.6917 (9)0.4348 (8)1.0509 (7)0.045 (5)0.181 (5)
H21M0.72000.45711.08920.067*0.181 (5)
H21N0.68860.39131.06220.067*0.181 (5)
H21O0.63890.45161.03900.067*0.181 (5)
O1B−0.02790 (9)0.62281 (9)0.82457 (9)0.0343 (4)
O2B0.08476 (9)0.58736 (8)0.75073 (8)0.0323 (4)
O3B0.11961 (9)0.45970 (8)0.72811 (8)0.0287 (4)
O4B0.00762 (10)0.37802 (10)0.75534 (9)0.0380 (5)
N1B0.23622 (11)0.59434 (9)0.73336 (9)0.0262 (5)
N2B0.24301 (11)0.48183 (9)0.67198 (10)0.0253 (5)
C1B0.10696 (13)0.62649 (11)0.80378 (11)0.0255 (5)
C2B0.04828 (13)0.64443 (11)0.84062 (12)0.0269 (6)
C3B0.06718 (14)0.68648 (11)0.89352 (12)0.0285 (6)
H3BA0.02780.69960.91720.034*
C4B0.14418 (14)0.70940 (11)0.91184 (12)0.0287 (6)
H4BA0.15600.73760.94760.034*
C5B0.20283 (14)0.69050 (11)0.87721 (11)0.0278 (6)
H5BA0.25450.70540.89010.033*
C6B0.18514 (13)0.64872 (11)0.82217 (11)0.0251 (5)
C7B0.24725 (13)0.63130 (11)0.78509 (12)0.0272 (6)
H7BA0.29790.64760.79930.033*
C8B0.30034 (13)0.58367 (11)0.69796 (11)0.0254 (5)
C9B0.35955 (13)0.62756 (12)0.69341 (11)0.0294 (6)
H9BA0.35820.66640.71420.035*
C10B0.42014 (14)0.61392 (13)0.65826 (12)0.0322 (6)
H10B0.46000.64340.65680.039*0.912 (5)
C11B0.42286 (13)0.55688 (13)0.62487 (12)0.0326 (6)
H11B0.46360.54830.60090.039*0.088 (5)
C12B0.36306 (13)0.51301 (12)0.62826 (12)0.0298 (6)
H12B0.36360.47480.60590.036*
C13B0.30267 (13)0.52601 (12)0.66482 (11)0.0265 (6)
C14B0.23733 (13)0.42342 (12)0.65070 (12)0.0278 (6)
H14B0.27450.40850.62570.033*
C15B0.17722 (13)0.38248 (11)0.66421 (12)0.0266 (6)
C16B0.17535 (14)0.31955 (12)0.64055 (13)0.0355 (6)
H16B0.21260.30620.61480.043*
C17B0.11951 (15)0.27888 (13)0.65529 (13)0.0392 (7)
H17B0.11880.23770.63990.047*
C18B0.06269 (14)0.29908 (13)0.69389 (13)0.0361 (6)
H18B0.02440.27110.70350.043*
C19B0.06291 (13)0.35899 (12)0.71741 (12)0.0298 (6)
C20B0.12030 (13)0.40368 (12)0.70386 (12)0.0270 (6)
C21B0.48833 (16)0.54276 (13)0.58557 (15)0.0375 (9)0.912 (5)
H21D0.53020.57300.59670.056*0.912 (5)
H21E0.46760.54470.53790.056*0.912 (5)
H21F0.50900.50160.59700.056*0.912 (5)
C21F0.5082 (15)0.6287 (13)0.6610 (14)0.033 (8)*0.088 (5)
H21S0.51610.67320.66430.049*0.088 (5)
H21T0.52480.61360.62050.049*0.088 (5)
H21U0.53890.60870.69980.049*0.088 (5)
O1C0.61613 (10)0.65594 (9)0.39257 (10)0.0369 (5)
O2C0.46109 (10)0.63085 (8)0.39791 (8)0.0291 (4)
O3C0.34742 (9)0.67350 (8)0.28067 (8)0.0296 (4)
O4C0.40206 (10)0.69348 (9)0.16221 (10)0.0411 (5)
N1C0.33732 (11)0.65233 (9)0.45702 (9)0.0263 (5)
N2C0.22571 (12)0.65583 (9)0.34223 (10)0.0251 (5)
C1C0.50298 (13)0.66524 (11)0.44890 (11)0.0255 (5)
C2C0.58275 (14)0.67692 (11)0.44600 (12)0.0288 (6)
C3C0.62882 (14)0.70965 (13)0.49781 (13)0.0369 (6)
H3CA0.68250.71630.49670.044*
C4C0.59594 (15)0.73281 (13)0.55160 (13)0.0397 (7)
H4CA0.62780.75440.58650.048*
C5C0.51658 (14)0.72393 (12)0.55351 (12)0.0323 (6)
H5CA0.49460.74060.58900.039*
C6C0.46872 (13)0.68982 (11)0.50200 (11)0.0263 (5)
C7C0.38493 (14)0.68150 (11)0.50396 (12)0.0269 (6)
H7CA0.36460.69780.54050.032*
C8C0.25654 (13)0.64372 (11)0.46340 (12)0.0265 (6)
C9C0.23143 (15)0.63346 (12)0.52487 (13)0.0348 (6)
H9CA0.26860.63420.56480.042*
C10C0.15256 (16)0.62218 (13)0.52787 (14)0.0414 (7)
H10C0.13700.61630.56970.050*0.734 (5)
C11C0.09631 (15)0.61948 (13)0.46909 (14)0.0391 (7)
H11C0.04330.61100.47110.047*0.266 (5)
C12C0.12025 (14)0.62955 (12)0.40712 (13)0.0335 (6)
H12C0.08300.62780.36740.040*
C13C0.19956 (14)0.64221 (11)0.40397 (12)0.0265 (6)
C14C0.18110 (14)0.66724 (11)0.28360 (12)0.0280 (6)
H14C0.12610.66640.28090.034*
C15C0.21183 (13)0.68077 (11)0.22438 (12)0.0266 (6)
C16C0.15820 (15)0.69103 (12)0.16293 (13)0.0372 (7)
H16C0.10360.69050.16260.045*
C17C0.18628 (16)0.70164 (13)0.10459 (13)0.0399 (7)
H17C0.15090.70860.06440.048*
C18C0.26869 (15)0.70220 (12)0.10455 (13)0.0346 (6)
H18C0.28710.70880.06410.041*
C19C0.32201 (14)0.69329 (11)0.16285 (12)0.0297 (6)
C20C0.29569 (14)0.68228 (11)0.22574 (12)0.0262 (5)
C21C0.01231 (19)0.6010 (2)0.47405 (18)0.0451 (12)0.734 (5)
H21G0.00800.59500.52080.068*0.734 (5)
H21H−0.00100.56270.44950.068*0.734 (5)
H21I−0.02360.63350.45500.068*0.734 (5)
C21G0.1144 (6)0.6217 (6)0.5868 (5)0.047 (3)0.266 (5)
H21P0.14330.64830.62120.070*0.266 (5)
H21Q0.11370.57980.60390.070*0.266 (5)
H21R0.06080.63680.57460.070*0.266 (5)
O1D0.39194 (9)0.77129 (8)0.36623 (10)0.0343 (4)
O2D0.49820 (10)0.76787 (8)0.28054 (9)0.0335 (4)
O3D0.54298 (9)0.64355 (8)0.26057 (8)0.0321 (4)
O4D0.43246 (10)0.55434 (9)0.27391 (9)0.0377 (5)
N1D0.64614 (11)0.79038 (9)0.26308 (10)0.0306 (5)
N2D0.66987 (11)0.67631 (9)0.21144 (10)0.0253 (5)
C1D0.51759 (14)0.80222 (11)0.33813 (12)0.0284 (6)
C2D0.46195 (14)0.80328 (11)0.38153 (13)0.0304 (6)
C3D0.47734 (15)0.83798 (12)0.44060 (13)0.0355 (6)
H3DA0.44060.83850.46990.043*
C4D0.54770 (15)0.87227 (12)0.45641 (13)0.0379 (6)
H4DA0.55700.89660.49550.045*
C5D0.60308 (15)0.87034 (12)0.41466 (13)0.0357 (6)
H5DA0.65000.89310.42580.043*
C6D0.58983 (14)0.83434 (11)0.35500 (13)0.0307 (6)
C7D0.65207 (14)0.82724 (12)0.31460 (13)0.0320 (6)
H7DA0.69850.85040.32650.038*
C8D0.71118 (14)0.78384 (12)0.22887 (12)0.0304 (6)
C9D0.76177 (15)0.83227 (13)0.21815 (13)0.0400 (7)
H9DA0.75330.87220.23420.048*
C10D0.82403 (17)0.82238 (14)0.18438 (14)0.0463 (7)
H10D0.85720.85570.17820.056*0.940 (6)
C11D0.83857 (15)0.76391 (14)0.15938 (13)0.0398 (7)
H11D0.88120.75760.13690.048*0.060 (6)
C12D0.78779 (14)0.71468 (13)0.16874 (12)0.0341 (6)
H12D0.79640.67500.15230.041*
C13D0.72434 (13)0.72481 (12)0.20252 (12)0.0273 (6)
C14D0.66857 (13)0.61896 (12)0.18750 (12)0.0283 (6)
H14D0.70820.60740.16330.034*
C15D0.61139 (13)0.57423 (11)0.19609 (12)0.0268 (6)
C16D0.61550 (14)0.51327 (12)0.16815 (13)0.0354 (6)
H16D0.65580.50370.14390.042*
C17D0.56089 (14)0.46882 (12)0.17668 (13)0.0360 (6)
H17D0.56420.42900.15860.043*
C18D0.49948 (14)0.48311 (12)0.21279 (12)0.0303 (6)
H18D0.46260.45240.21840.036*
C19D0.49304 (13)0.54098 (11)0.23962 (11)0.0260 (6)
C20D0.54951 (13)0.58924 (11)0.23323 (11)0.0259 (6)
C21D0.90795 (16)0.75283 (15)0.12341 (16)0.0490 (10)0.940 (6)
H21J0.94320.78820.13020.074*0.940 (6)
H21K0.88880.74740.07580.074*0.940 (6)
H21L0.93600.71580.14130.074*0.940 (6)
C21H0.900 (4)0.848 (3)0.164 (3)0.08 (2)*0.060 (6)
H21V0.91730.88420.19130.127*0.060 (6)
H21W0.88950.85960.11720.127*0.060 (6)
H21X0.94050.81650.17140.127*0.060 (6)
H1OA1.161 (2)0.4665 (16)0.8211 (17)0.085 (12)*
H1OB−0.0314 (16)0.5904 (14)0.7999 (14)0.050 (10)*
H1OC0.581 (2)0.6478 (17)0.3561 (18)0.094 (14)*
H1OD0.396 (2)0.7436 (16)0.3327 (17)0.085 (12)*
H2OA0.9859 (19)0.4770 (15)0.8730 (16)0.081 (11)*
H2OB0.1312 (17)0.5778 (13)0.7319 (14)0.061 (9)*
H2OC0.4060 (18)0.6322 (14)0.4069 (15)0.072 (10)*
H2OD0.5446 (18)0.7653 (14)0.2607 (15)0.065 (10)*
H4OA0.997 (3)0.533 (2)0.676 (2)0.130 (19)*
H4OB0.014 (2)0.4197 (17)0.7643 (17)0.088 (13)*
H4OC0.426 (2)0.6875 (19)0.2045 (19)0.110 (15)*
H4OD0.436 (2)0.5922 (16)0.2872 (17)0.082 (13)*
H2NA0.8542 (18)0.4897 (14)0.8169 (14)0.062 (9)*
H2NB0.1992 (18)0.4912 (14)0.6998 (14)0.072 (10)*
H2NC0.2810 (15)0.6585 (11)0.3414 (12)0.040 (7)*
H2ND0.6257 (16)0.6842 (12)0.2352 (13)0.051 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0209 (9)0.0591 (13)0.0297 (11)−0.0017 (9)0.0056 (9)0.0028 (9)
O2A0.0201 (9)0.0424 (11)0.0371 (10)0.0054 (8)0.0054 (8)0.0064 (9)
O3A0.0271 (9)0.0517 (12)0.0368 (11)−0.0115 (9)−0.0041 (9)0.0051 (9)
O4A0.0430 (13)0.104 (2)0.0374 (13)−0.0274 (12)0.0013 (11)0.0070 (13)
N1A0.0220 (11)0.0296 (12)0.0395 (13)−0.0022 (9)0.0060 (10)−0.0041 (10)
N2A0.0201 (11)0.0263 (12)0.0493 (15)−0.0004 (9)−0.0012 (11)0.0061 (10)
C1A0.0212 (12)0.0264 (14)0.0287 (14)0.0022 (10)0.0000 (11)−0.0029 (11)
C2A0.0210 (12)0.0400 (16)0.0247 (13)0.0009 (11)0.0033 (11)−0.0030 (12)
C3A0.0195 (12)0.0508 (18)0.0330 (15)0.0020 (12)0.0015 (12)−0.0022 (13)
C4A0.0285 (14)0.060 (2)0.0360 (16)0.0028 (13)0.0011 (12)0.0113 (14)
C5A0.0296 (14)0.0522 (19)0.0358 (16)−0.0038 (13)0.0067 (13)0.0089 (14)
C6A0.0211 (12)0.0323 (15)0.0339 (15)0.0004 (11)0.0034 (11)−0.0005 (12)
C7A0.0240 (13)0.0358 (16)0.0393 (16)0.0007 (12)0.0101 (12)0.0021 (13)
C8A0.0213 (13)0.0260 (15)0.0487 (17)0.0010 (11)0.0068 (13)−0.0011 (12)
C9A0.0314 (14)0.0347 (16)0.0466 (17)0.0006 (12)0.0132 (13)−0.0049 (13)
C10A0.0285 (14)0.0337 (16)0.0525 (18)−0.0009 (12)0.0128 (14)−0.0038 (14)
C11A0.0291 (14)0.0231 (15)0.064 (2)−0.0011 (11)0.0198 (15)0.0003 (13)
C12A0.0239 (13)0.0250 (15)0.0611 (19)0.0034 (11)0.0021 (13)0.0035 (13)
C13A0.0278 (14)0.0209 (14)0.0528 (17)−0.0013 (11)0.0140 (13)0.0039 (12)
C14A0.0216 (13)0.0214 (14)0.0567 (19)−0.0001 (11)0.0022 (14)0.0020 (13)
C15A0.0264 (13)0.0189 (14)0.0465 (17)−0.0007 (11)−0.0081 (13)−0.0033 (12)
C16A0.0341 (15)0.0325 (17)0.0541 (19)−0.0015 (12)−0.0038 (14)−0.0025 (14)
C17A0.0420 (17)0.0375 (17)0.0480 (19)0.0023 (14)−0.0187 (15)−0.0061 (14)
C18A0.0564 (19)0.0385 (18)0.0376 (17)−0.0058 (14)−0.0060 (15)−0.0007 (13)
C19A0.0370 (16)0.0421 (18)0.0427 (17)−0.0107 (13)−0.0032 (14)−0.0004 (14)
C20A0.0355 (15)0.0308 (16)0.0364 (16)−0.0059 (12)−0.0007 (13)0.0021 (12)
C21A0.0231 (16)0.035 (2)0.0370 (19)0.0034 (14)0.0049 (14)0.0114 (15)
C21E0.055 (10)0.054 (11)0.034 (9)−0.007 (8)0.032 (8)−0.009 (8)
O1B0.0224 (9)0.0408 (12)0.0392 (11)−0.0016 (8)0.0038 (8)−0.0051 (10)
O2B0.0224 (9)0.0391 (11)0.0353 (10)−0.0022 (8)0.0045 (8)−0.0096 (9)
O3B0.0265 (9)0.0287 (10)0.0308 (9)−0.0024 (7)0.0046 (8)−0.0038 (8)
O4B0.0315 (10)0.0412 (12)0.0421 (11)−0.0112 (9)0.0092 (9)−0.0074 (10)
N1B0.0233 (10)0.0295 (12)0.0257 (11)−0.0024 (9)0.0040 (9)0.0008 (10)
N2B0.0213 (10)0.0284 (13)0.0249 (11)−0.0006 (9)0.0005 (9)−0.0005 (9)
C1B0.0281 (13)0.0237 (14)0.0234 (13)0.0000 (11)0.0005 (11)0.0010 (11)
C2B0.0226 (13)0.0274 (14)0.0296 (14)0.0017 (11)0.0014 (11)0.0069 (11)
C3B0.0295 (13)0.0294 (15)0.0272 (14)0.0050 (11)0.0064 (11)0.0059 (12)
C4B0.0366 (14)0.0235 (14)0.0253 (13)−0.0002 (11)0.0040 (12)0.0020 (11)
C5B0.0266 (13)0.0289 (15)0.0264 (13)−0.0038 (11)0.0001 (11)0.0028 (11)
C6B0.0264 (13)0.0235 (14)0.0255 (13)−0.0002 (10)0.0047 (11)0.0043 (11)
C7B0.0224 (12)0.0306 (15)0.0270 (14)−0.0054 (11)0.0001 (11)0.0039 (12)
C8B0.0194 (12)0.0324 (15)0.0231 (13)−0.0010 (11)0.0006 (10)0.0022 (11)
C9B0.0299 (13)0.0344 (15)0.0228 (13)−0.0064 (11)0.0018 (11)0.0021 (11)
C10B0.0255 (13)0.0451 (17)0.0251 (13)−0.0058 (12)0.0022 (11)0.0060 (13)
C11B0.0219 (13)0.0464 (17)0.0298 (14)0.0047 (12)0.0056 (11)0.0133 (13)
C12B0.0266 (13)0.0358 (16)0.0261 (14)0.0054 (11)0.0022 (11)0.0048 (11)
C13B0.0198 (12)0.0369 (16)0.0218 (13)−0.0023 (11)0.0011 (10)0.0070 (11)
C14B0.0211 (12)0.0366 (16)0.0238 (13)0.0049 (11)−0.0011 (11)−0.0008 (12)
C15B0.0198 (12)0.0281 (15)0.0287 (14)0.0012 (10)−0.0045 (11)−0.0007 (11)
C16B0.0259 (13)0.0373 (17)0.0408 (16)0.0034 (12)−0.0010 (12)−0.0083 (13)
C17B0.0347 (15)0.0315 (16)0.0462 (17)−0.0004 (12)−0.0077 (13)−0.0083 (13)
C18B0.0281 (14)0.0375 (17)0.0395 (16)−0.0079 (12)−0.0028 (12)−0.0031 (13)
C19B0.0219 (13)0.0362 (16)0.0285 (14)−0.0037 (11)−0.0033 (11)0.0007 (12)
C20B0.0223 (12)0.0302 (15)0.0256 (13)−0.0011 (11)−0.0037 (11)−0.0008 (11)
C21B0.0323 (16)0.0345 (18)0.0495 (19)0.0055 (13)0.0175 (15)0.0062 (14)
O1C0.0245 (10)0.0464 (12)0.0390 (11)0.0054 (8)0.0035 (9)−0.0122 (9)
O2C0.0237 (9)0.0327 (10)0.0288 (10)0.0025 (8)−0.0011 (8)−0.0074 (8)
O3C0.0229 (9)0.0368 (10)0.0267 (9)−0.0018 (7)−0.0021 (8)0.0042 (8)
O4C0.0310 (10)0.0567 (13)0.0360 (12)−0.0101 (9)0.0069 (9)0.0044 (10)
N1C0.0255 (11)0.0289 (12)0.0237 (11)0.0034 (9)0.0020 (9)0.0028 (9)
N2C0.0236 (11)0.0236 (12)0.0271 (12)0.0001 (9)0.0014 (10)0.0010 (9)
C1C0.0266 (13)0.0252 (14)0.0219 (13)0.0038 (11)−0.0038 (11)−0.0002 (11)
C2C0.0263 (13)0.0310 (15)0.0272 (14)0.0065 (11)−0.0003 (11)−0.0008 (12)
C3C0.0225 (13)0.0478 (18)0.0374 (16)0.0005 (12)−0.0035 (12)−0.0044 (14)
C4C0.0346 (15)0.0492 (18)0.0309 (15)−0.0034 (13)−0.0068 (13)−0.0050 (13)
C5C0.0346 (15)0.0368 (16)0.0238 (14)0.0034 (12)0.0006 (12)−0.0023 (12)
C6C0.0280 (13)0.0260 (14)0.0233 (13)0.0052 (11)−0.0001 (11)0.0025 (11)
C7C0.0318 (14)0.0259 (14)0.0227 (13)0.0040 (11)0.0036 (11)0.0034 (11)
C8C0.0256 (13)0.0244 (14)0.0294 (14)0.0017 (10)0.0049 (11)0.0013 (11)
C9C0.0386 (15)0.0385 (16)0.0271 (14)−0.0011 (12)0.0047 (12)0.0030 (12)
C10C0.0397 (16)0.0514 (19)0.0362 (16)−0.0084 (14)0.0152 (14)0.0001 (14)
C11C0.0289 (14)0.0431 (17)0.0467 (17)−0.0053 (12)0.0106 (13)−0.0028 (14)
C12C0.0244 (13)0.0367 (16)0.0377 (15)−0.0036 (11)0.0009 (12)0.0002 (13)
C13C0.0280 (13)0.0220 (14)0.0302 (14)0.0027 (10)0.0068 (11)0.0019 (11)
C14C0.0253 (13)0.0261 (14)0.0304 (14)0.0000 (11)−0.0014 (11)−0.0016 (11)
C15C0.0260 (13)0.0246 (14)0.0278 (14)−0.0014 (10)0.0007 (11)0.0011 (11)
C16C0.0274 (14)0.0459 (18)0.0347 (16)0.0000 (12)−0.0046 (12)0.0028 (13)
C17C0.0402 (16)0.0441 (18)0.0313 (15)−0.0036 (13)−0.0055 (13)0.0060 (13)
C18C0.0446 (16)0.0317 (16)0.0268 (14)−0.0077 (12)0.0044 (13)0.0042 (12)
C19C0.0316 (14)0.0268 (15)0.0299 (14)−0.0058 (11)0.0037 (12)0.0002 (11)
C20C0.0297 (13)0.0181 (13)0.0288 (14)−0.0019 (10)−0.0002 (11)0.0006 (11)
C21C0.027 (2)0.069 (3)0.038 (2)−0.0055 (19)0.0046 (17)0.009 (2)
C21G0.036 (6)0.076 (9)0.027 (6)−0.005 (6)0.004 (5)0.019 (6)
O1D0.0259 (9)0.0301 (11)0.0460 (12)0.0031 (8)0.0037 (9)0.0005 (9)
O2D0.0280 (10)0.0285 (10)0.0428 (11)−0.0005 (8)0.0026 (9)−0.0054 (8)
O3D0.0330 (9)0.0264 (10)0.0377 (10)−0.0069 (8)0.0088 (8)−0.0068 (8)
O4D0.0372 (11)0.0342 (12)0.0443 (12)−0.0134 (9)0.0142 (9)−0.0092 (9)
N1D0.0303 (11)0.0249 (12)0.0353 (12)−0.0005 (9)0.0023 (10)0.0026 (10)
N2D0.0194 (10)0.0268 (12)0.0281 (11)−0.0023 (9)−0.0001 (9)0.0025 (10)
C1D0.0295 (14)0.0194 (14)0.0334 (15)0.0044 (11)−0.0026 (12)0.0021 (11)
C2D0.0280 (14)0.0214 (14)0.0402 (16)0.0075 (11)0.0012 (12)0.0050 (12)
C3D0.0332 (15)0.0326 (16)0.0401 (16)0.0090 (12)0.0045 (13)0.0037 (13)
C4D0.0379 (15)0.0357 (16)0.0376 (16)0.0047 (13)0.0000 (13)−0.0030 (13)
C5D0.0297 (14)0.0316 (16)0.0422 (16)0.0020 (12)−0.0041 (13)−0.0013 (13)
C6D0.0291 (14)0.0248 (14)0.0359 (15)0.0052 (11)−0.0009 (12)0.0028 (12)
C7D0.0254 (13)0.0279 (15)0.0390 (16)−0.0023 (11)−0.0046 (12)0.0068 (13)
C8D0.0268 (13)0.0299 (15)0.0325 (14)−0.0041 (11)−0.0002 (12)0.0051 (12)
C9D0.0459 (16)0.0308 (16)0.0434 (17)−0.0101 (13)0.0081 (14)0.0021 (13)
C10D0.0480 (17)0.0411 (19)0.0511 (18)−0.0148 (14)0.0119 (15)0.0058 (15)
C11D0.0280 (14)0.0517 (19)0.0397 (16)−0.0071 (13)0.0061 (13)0.0080 (14)
C12D0.0263 (13)0.0379 (16)0.0361 (15)−0.0034 (12)−0.0001 (12)0.0007 (12)
C13D0.0177 (12)0.0352 (16)0.0258 (13)−0.0049 (11)−0.0047 (10)0.0057 (11)
C14D0.0198 (12)0.0322 (16)0.0313 (14)0.0038 (11)0.0004 (11)−0.0012 (12)
C15D0.0186 (12)0.0279 (15)0.0314 (14)0.0004 (10)−0.0024 (11)0.0006 (11)
C16D0.0247 (13)0.0331 (16)0.0475 (17)0.0048 (12)0.0040 (12)−0.0042 (13)
C17D0.0321 (14)0.0210 (14)0.0506 (17)0.0035 (12)−0.0049 (13)−0.0070 (13)
C18D0.0249 (13)0.0267 (15)0.0352 (15)−0.0033 (11)−0.0062 (11)0.0011 (12)
C19D0.0229 (12)0.0288 (15)0.0247 (13)−0.0034 (11)−0.0006 (11)0.0020 (11)
C20D0.0240 (13)0.0251 (15)0.0255 (13)0.0002 (11)−0.0039 (11)0.0016 (11)
C21D0.0363 (17)0.056 (2)0.059 (2)−0.0139 (15)0.0185 (16)−0.0038 (17)

Geometric parameters (Å, °)

O1A—C2A1.367 (3)O1C—C2C1.372 (3)
O1A—H1OA0.89 (3)O1C—H1OC0.87 (4)
O2A—C1A1.351 (3)O2C—C1C1.356 (3)
O2A—H2OA0.91 (3)O2C—H2OC0.99 (3)
O3A—C20A1.289 (3)O3C—C20C1.299 (3)
O4A—C19A1.372 (3)O4C—C19C1.368 (3)
O4A—H4OA0.81 (4)O4C—H4OC0.89 (4)
N1A—C7A1.286 (3)N1C—C7C1.291 (3)
N1A—C8A1.421 (3)N1C—C8C1.418 (3)
N2A—C14A1.309 (3)N2C—C14C1.307 (3)
N2A—C13A1.416 (3)N2C—C13C1.416 (3)
N2A—H2NA0.92 (3)N2C—H2NC0.95 (2)
C1A—C2A1.397 (3)C1C—C2C1.395 (3)
C1A—C6A1.397 (3)C1C—C6C1.401 (3)
C2A—C3A1.380 (3)C2C—C3C1.378 (3)
C3A—C4A1.384 (3)C3C—C4C1.389 (3)
C3A—H3AA0.93C3C—H3CA0.93
C4A—C5A1.378 (3)C4C—C5C1.375 (3)
C4A—H4AA0.93C4C—H4CA0.93
C5A—C6A1.398 (3)C5C—C6C1.403 (3)
C5A—H5AA0.93C5C—H5CA0.93
C6A—C7A1.448 (3)C6C—C7C1.448 (3)
C7A—H7AA0.93C7C—H7CA0.93
C8A—C13A1.395 (3)C8C—C9C1.389 (3)
C8A—C9A1.401 (3)C8C—C13C1.401 (3)
C9A—C10A1.376 (3)C9C—C10C1.379 (3)
C9A—H9AA0.93C9C—H9CA0.93
C10A—C21E1.251 (12)C10C—C11C1.385 (4)
C10A—C11A1.376 (4)C10C—C21G1.445 (9)
C10A—H10A0.93C10C—H10C0.93
C11A—C12A1.386 (3)C11C—C12C1.389 (3)
C11A—C21A1.518 (3)C11C—C21C1.506 (4)
C11A—H11A0.93C11C—H11C0.93
C12A—C13A1.399 (3)C12C—C13C1.392 (3)
C12A—H12A0.93C12C—H12C0.93
C14A—C15A1.404 (3)C14C—C15C1.407 (3)
C14A—H14A0.93C14C—H14C0.93
C15A—C16A1.414 (4)C15C—C16C1.418 (3)
C15A—C20A1.434 (3)C15C—C20C1.427 (3)
C16A—C17A1.348 (4)C16C—C17C1.357 (3)
C16A—H16A0.93C16C—H16C0.93
C17A—C18A1.419 (4)C17C—C18C1.406 (3)
C17A—H17A0.93C17C—H17C0.93
C18A—C19A1.362 (4)C18C—C19C1.364 (3)
C18A—H18A0.93C18C—H18C0.93
C19A—C20A1.429 (3)C19C—C20C1.428 (3)
C21A—H21A0.96C21C—H21G0.96
C21A—H21B0.96C21C—H21H0.96
C21A—H21C0.96C21C—H21I0.96
C21E—H21M0.96C21G—H21P0.96
C21E—H21N0.96C21G—H21Q0.96
C21E—H21O0.96C21G—H21R0.96
O1B—C2B1.364 (3)O1D—C2D1.364 (3)
O1B—H1OB0.85 (3)O1D—H1OD0.91 (3)
O2B—C1B1.353 (3)O2D—C1D1.358 (3)
O2B—H2OB0.96 (3)O2D—H2OD0.95 (3)
O3B—C20B1.292 (3)O3D—C20D1.295 (3)
O4B—C19B1.371 (3)O4D—C19D1.367 (3)
O4B—H4OB0.91 (4)O4D—H4OD0.85 (3)
N1B—C7B1.290 (3)N1D—C7D1.288 (3)
N1B—C8B1.422 (3)N1D—C8D1.409 (3)
N2B—C14B1.316 (3)N2D—C14D1.313 (3)
N2B—C13B1.413 (3)N2D—C13D1.423 (3)
N2B—H2NB1.03 (3)N2D—H2ND0.97 (3)
C1B—C2B1.396 (3)C1D—C2D1.394 (3)
C1B—C6B1.404 (3)C1D—C6D1.400 (3)
C2B—C3B1.383 (3)C2D—C3D1.382 (3)
C3B—C4B1.390 (3)C3D—C4D1.395 (3)
C3B—H3BA0.93C3D—H3DA0.93
C4B—C5B1.373 (3)C4D—C5D1.367 (3)
C4B—H4BA0.93C4D—H4DA0.93
C5B—C6B1.409 (3)C5D—C6D1.406 (3)
C5B—H5BA0.93C5D—H5DA0.93
C6B—C7B1.444 (3)C6D—C7D1.450 (3)
C7B—H7BA0.93C7D—H7DA0.93
C8B—C9B1.392 (3)C8D—C9D1.387 (3)
C8B—C13B1.402 (3)C8D—C13D1.399 (3)
C9B—C10B1.379 (3)C9D—C10D1.371 (4)
C9B—H9BA0.93C9D—H9DA0.93
C10B—C11B1.394 (4)C10D—C11D1.383 (4)
C10B—C21F1.53 (3)C10D—C21H1.52 (6)
C10B—H10B0.93C10D—H10D0.93
C11B—C12B1.395 (3)C11D—C12D1.395 (3)
C11B—C21B1.504 (3)C11D—C21D1.507 (3)
C11B—H11B0.93C11D—H11D0.93
C12B—C13B1.392 (3)C12D—C13D1.390 (3)
C12B—H12B0.93C12D—H12D0.93
C14B—C15B1.409 (3)C14D—C15D1.397 (3)
C14B—H14B0.93C14D—H14D0.93
C15B—C16B1.423 (3)C15D—C16D1.423 (3)
C15B—C20B1.430 (3)C15D—C20D1.429 (3)
C16B—C17B1.359 (3)C16D—C17D1.361 (3)
C16B—H16B0.93C16D—H16D0.93
C17B—C18B1.408 (3)C17D—C18D1.406 (3)
C17B—H17B0.93C17D—H17D0.93
C18B—C19B1.363 (3)C18D—C19D1.359 (3)
C18B—H18B0.93C18D—H18D0.93
C19B—C20B1.426 (3)C19D—C20D1.431 (3)
C21B—H21D0.96C21D—H21J0.96
C21B—H21E0.96C21D—H21K0.96
C21B—H21F0.96C21D—H21L0.96
C21F—H21S0.96C21H—H21V0.96
C21F—H21T0.96C21H—H21W0.96
C21F—H21U0.96C21H—H21X0.96
C2A—O1A—H1OA117 (2)C2C—O1C—H1OC114 (2)
C1A—O2A—H2OA106 (2)C1C—O2C—H2OC104.0 (18)
C19A—O4A—H4OA111 (3)C19C—O4C—H4OC107 (2)
C7A—N1A—C8A118.8 (2)C7C—N1C—C8C119.7 (2)
C14A—N2A—C13A126.7 (2)C14C—N2C—C13C126.9 (2)
C14A—N2A—H2NA112.6 (18)C14C—N2C—H2NC113.5 (15)
C13A—N2A—H2NA120.6 (18)C13C—N2C—H2NC119.6 (15)
O2A—C1A—C2A116.8 (2)O2C—C1C—C2C117.1 (2)
O2A—C1A—C6A123.5 (2)O2C—C1C—C6C122.6 (2)
C2A—C1A—C6A119.7 (2)C2C—C1C—C6C120.2 (2)
O1A—C2A—C3A119.5 (2)O1C—C2C—C3C119.5 (2)
O1A—C2A—C1A120.5 (2)O1C—C2C—C1C120.9 (2)
C3A—C2A—C1A119.9 (2)C3C—C2C—C1C119.5 (2)
C2A—C3A—C4A120.6 (2)C2C—C3C—C4C120.7 (2)
C2A—C3A—H3AA119.7C2C—C3C—H3CA119.7
C4A—C3A—H3AA119.7C4C—C3C—H3CA119.7
C5A—C4A—C3A120.0 (2)C5C—C4C—C3C120.3 (2)
C5A—C4A—H4AA120.0C5C—C4C—H4CA119.8
C3A—C4A—H4AA120.0C3C—C4C—H4CA119.8
C4A—C5A—C6A120.4 (2)C4C—C5C—C6C120.1 (2)
C4A—C5A—H5AA119.8C4C—C5C—H5CA119.9
C6A—C5A—H5AA119.8C6C—C5C—H5CA119.9
C1A—C6A—C5A119.4 (2)C1C—C6C—C5C119.1 (2)
C1A—C6A—C7A121.5 (2)C1C—C6C—C7C121.2 (2)
C5A—C6A—C7A119.1 (2)C5C—C6C—C7C119.7 (2)
N1A—C7A—C6A123.8 (2)N1C—C7C—C6C122.6 (2)
N1A—C7A—H7AA118.1N1C—C7C—H7CA118.7
C6A—C7A—H7AA118.1C6C—C7C—H7CA118.7
C13A—C8A—C9A117.8 (2)C9C—C8C—C13C118.3 (2)
C13A—C8A—N1A117.8 (2)C9C—C8C—N1C123.6 (2)
C9A—C8A—N1A124.3 (2)C13C—C8C—N1C118.0 (2)
C10A—C9A—C8A121.3 (3)C10C—C9C—C8C121.3 (2)
C10A—C9A—H9AA119.3C10C—C9C—H9CA119.4
C8A—C9A—H9AA119.3C8C—C9C—H9CA119.4
C21E—C10A—C9A132.1 (8)C9C—C10C—C11C120.5 (2)
C21E—C10A—C11A106.8 (8)C9C—C10C—C21G128.2 (5)
C9A—C10A—C11A120.9 (3)C11C—C10C—C21G110.5 (5)
C9A—C10A—H10A119.6C9C—C10C—H10C119.7
C11A—C10A—H10A119.6C11C—C10C—H10C119.7
C10A—C11A—C12A118.9 (2)C10C—C11C—C12C119.0 (2)
C10A—C11A—C21A119.4 (2)C10C—C11C—C21C118.8 (3)
C12A—C11A—C21A121.7 (3)C12C—C11C—C21C122.0 (3)
C10A—C11A—H11A120.5C10C—C11C—H11C120.5
C12A—C11A—H11A120.5C12C—C11C—H11C120.5
C11A—C12A—C13A120.8 (3)C11C—C12C—C13C120.6 (2)
C11A—C12A—H12A119.6C11C—C12C—H12C119.7
C13A—C12A—H12A119.6C13C—C12C—H12C119.7
C8A—C13A—C12A120.2 (2)C12C—C13C—C8C120.2 (2)
C8A—C13A—N2A118.7 (2)C12C—C13C—N2C122.4 (2)
C12A—C13A—N2A121.0 (2)C8C—C13C—N2C117.4 (2)
N2A—C14A—C15A124.0 (2)N2C—C14C—C15C123.5 (2)
N2A—C14A—H14A118.0N2C—C14C—H14C118.3
C15A—C14A—H14A118.0C15C—C14C—H14C118.3
C14A—C15A—C16A119.7 (2)C14C—C15C—C16C119.0 (2)
C14A—C15A—C20A120.3 (2)C14C—C15C—C20C120.5 (2)
C16A—C15A—C20A120.0 (2)C16C—C15C—C20C120.5 (2)
C17A—C16A—C15A120.9 (3)C17C—C16C—C15C120.2 (2)
C17A—C16A—H16A119.6C17C—C16C—H16C119.9
C15A—C16A—H16A119.6C15C—C16C—H16C119.9
C16A—C17A—C18A120.5 (3)C16C—C17C—C18C120.3 (2)
C16A—C17A—H17A119.8C16C—C17C—H17C119.9
C18A—C17A—H17A119.8C18C—C17C—H17C119.9
C19A—C18A—C17A120.1 (3)C19C—C18C—C17C121.1 (2)
C19A—C18A—H18A120.0C19C—C18C—H18C119.4
C17A—C18A—H18A120.0C17C—C18C—H18C119.4
C18A—C19A—O4A120.7 (3)C18C—C19C—O4C120.7 (2)
C18A—C19A—C20A121.7 (3)C18C—C19C—C20C120.9 (2)
O4A—C19A—C20A117.6 (2)O4C—C19C—C20C118.4 (2)
O3A—C20A—C19A120.1 (2)O3C—C20C—C15C123.0 (2)
O3A—C20A—C15A123.1 (2)O3C—C20C—C19C120.0 (2)
C19A—C20A—C15A116.8 (2)C15C—C20C—C19C117.0 (2)
C11A—C21A—H21A109.5C11C—C21C—H21G109.5
C11A—C21A—H21B109.5C11C—C21C—H21H109.5
C11A—C21A—H21C109.5C11C—C21C—H21I109.5
C10A—C21E—H21M109.5C10C—C21G—H21P109.5
C10A—C21E—H21N109.5C10C—C21G—H21Q109.5
H21M—C21E—H21N109.5H21P—C21G—H21Q109.5
C10A—C21E—H21O109.5C10C—C21G—H21R109.5
H21M—C21E—H21O109.5H21P—C21G—H21R109.5
H21N—C21E—H21O109.5H21Q—C21G—H21R109.5
C2B—O1B—H1OB112.4 (19)C2D—O1D—H1OD108 (2)
C1B—O2B—H2OB107.6 (17)C1D—O2D—H2OD106.8 (18)
C19B—O4B—H4OB109 (2)C19D—O4D—H4OD110 (2)
C7B—N1B—C8B118.75 (19)C7D—N1D—C8D119.4 (2)
C14B—N2B—C13B127.8 (2)C14D—N2D—C13D127.0 (2)
C14B—N2B—H2NB109.9 (17)C14D—N2D—H2ND111.9 (16)
C13B—N2B—H2NB122.0 (17)C13D—N2D—H2ND120.9 (16)
O2B—C1B—C2B117.1 (2)O2D—C1D—C2D116.5 (2)
O2B—C1B—C6B122.6 (2)O2D—C1D—C6D123.0 (2)
C2B—C1B—C6B120.3 (2)C2D—C1D—C6D120.5 (2)
O1B—C2B—C3B119.1 (2)O1D—C2D—C3D119.3 (2)
O1B—C2B—C1B121.6 (2)O1D—C2D—C1D121.1 (2)
C3B—C2B—C1B119.3 (2)C3D—C2D—C1D119.6 (2)
C2B—C3B—C4B121.0 (2)C2D—C3D—C4D120.3 (2)
C2B—C3B—H3BA119.5C2D—C3D—H3DA119.9
C4B—C3B—H3BA119.5C4D—C3D—H3DA119.9
C5B—C4B—C3B120.1 (2)C5D—C4D—C3D120.3 (3)
C5B—C4B—H4BA120.0C5D—C4D—H4DA119.8
C3B—C4B—H4BA120.0C3D—C4D—H4DA119.8
C4B—C5B—C6B120.3 (2)C4D—C5D—C6D120.7 (2)
C4B—C5B—H5BA119.8C4D—C5D—H5DA119.7
C6B—C5B—H5BA119.8C6D—C5D—H5DA119.7
C1B—C6B—C5B119.0 (2)C1D—C6D—C5D118.6 (2)
C1B—C6B—C7B121.8 (2)C1D—C6D—C7D120.9 (2)
C5B—C6B—C7B119.2 (2)C5D—C6D—C7D120.4 (2)
N1B—C7B—C6B123.5 (2)N1D—C7D—C6D123.2 (2)
N1B—C7B—H7BA118.2N1D—C7D—H7DA118.4
C6B—C7B—H7BA118.2C6D—C7D—H7DA118.4
C9B—C8B—C13B118.6 (2)C9D—C8D—C13D117.9 (2)
C9B—C8B—N1B123.7 (2)C9D—C8D—N1D124.4 (2)
C13B—C8B—N1B117.6 (2)C13D—C8D—N1D117.7 (2)
C10B—C9B—C8B120.5 (2)C10D—C9D—C8D121.2 (3)
C10B—C9B—H9BA119.7C10D—C9D—H9DA119.4
C8B—C9B—H9BA119.7C8D—C9D—H9DA119.4
C9B—C10B—C11B121.3 (2)C9D—C10D—C11D121.4 (3)
C9B—C10B—C21F139.3 (11)C9D—C10D—C21H147 (3)
C11B—C10B—C21F94.8 (11)C11D—C10D—C21H91 (3)
C9B—C10B—H10B119.3C9D—C10D—H10D119.3
C11B—C10B—H10B119.3C11D—C10D—H10D119.3
C10B—C11B—C12B118.5 (2)C10D—C11D—C12D118.5 (2)
C10B—C11B—C21B121.0 (2)C10D—C11D—C21D121.3 (2)
C12B—C11B—C21B120.4 (2)C12D—C11D—C21D120.2 (3)
C10B—C11B—H11B120.7C10D—C11D—H11D120.8
C12B—C11B—H11B120.7C12D—C11D—H11D120.8
C13B—C12B—C11B120.4 (2)C13D—C12D—C11D120.2 (2)
C13B—C12B—H12B119.8C13D—C12D—H12D119.9
C11B—C12B—H12B119.8C11D—C12D—H12D119.9
C12B—C13B—C8B120.5 (2)C12D—C13D—C8D120.9 (2)
C12B—C13B—N2B122.2 (2)C12D—C13D—N2D121.9 (2)
C8B—C13B—N2B117.25 (19)C8D—C13D—N2D117.2 (2)
N2B—C14B—C15B122.7 (2)N2D—C14D—C15D124.1 (2)
N2B—C14B—H14B118.6N2D—C14D—H14D118.0
C15B—C14B—H14B118.6C15D—C14D—H14D118.0
C14B—C15B—C16B119.8 (2)C14D—C15D—C16D119.6 (2)
C14B—C15B—C20B119.8 (2)C14D—C15D—C20D120.4 (2)
C16B—C15B—C20B120.4 (2)C16D—C15D—C20D120.1 (2)
C17B—C16B—C15B120.5 (2)C17D—C16D—C15D120.4 (2)
C17B—C16B—H16B119.8C17D—C16D—H16D119.8
C15B—C16B—H16B119.8C15D—C16D—H16D119.8
C16B—C17B—C18B119.9 (2)C16D—C17D—C18D120.1 (2)
C16B—C17B—H17B120.0C16D—C17D—H17D120.0
C18B—C17B—H17B120.0C18D—C17D—H17D120.0
C19B—C18B—C17B121.1 (2)C19D—C18D—C17D121.3 (2)
C19B—C18B—H18B119.5C19D—C18D—H18D119.4
C17B—C18B—H18B119.5C17D—C18D—H18D119.4
C18B—C19B—O4B120.6 (2)C18D—C19D—O4D120.6 (2)
C18B—C19B—C20B121.5 (2)C18D—C19D—C20D121.1 (2)
O4B—C19B—C20B117.9 (2)O4D—C19D—C20D118.3 (2)
O3B—C20B—C19B119.8 (2)O3D—C20D—C15D123.1 (2)
O3B—C20B—C15B123.6 (2)O3D—C20D—C19D119.9 (2)
C19B—C20B—C15B116.7 (2)C15D—C20D—C19D117.0 (2)
C11B—C21B—H21D109.5C11D—C21D—H21J109.5
C11B—C21B—H21E109.5C11D—C21D—H21K109.5
C11B—C21B—H21F109.5C11D—C21D—H21L109.5
C10B—C21F—H21S109.5C10D—C21H—H21V109.5
C10B—C21F—H21T109.5C10D—C21H—H21W109.5
H21S—C21F—H21T109.5H21V—C21H—H21W109.5
C10B—C21F—H21U109.5C10D—C21H—H21X109.5
H21S—C21F—H21U109.5H21V—C21H—H21X109.5
H21T—C21F—H21U109.5H21W—C21H—H21X109.5
O2A—C1A—C2A—O1A0.2 (3)O2C—C1C—C2C—O1C1.9 (3)
C6A—C1A—C2A—O1A−179.2 (2)C6C—C1C—C2C—O1C−176.6 (2)
O2A—C1A—C2A—C3A178.5 (2)O2C—C1C—C2C—C3C−177.6 (2)
C6A—C1A—C2A—C3A−0.8 (4)C6C—C1C—C2C—C3C3.8 (4)
O1A—C2A—C3A—C4A178.4 (2)O1C—C2C—C3C—C4C178.3 (2)
C1A—C2A—C3A—C4A0.1 (4)C1C—C2C—C3C—C4C−2.1 (4)
C2A—C3A—C4A—C5A0.1 (4)C2C—C3C—C4C—C5C−0.7 (4)
C3A—C4A—C5A—C6A0.5 (4)C3C—C4C—C5C—C6C1.8 (4)
O2A—C1A—C6A—C5A−177.9 (2)O2C—C1C—C6C—C5C178.8 (2)
C2A—C1A—C6A—C5A1.4 (4)C2C—C1C—C6C—C5C−2.7 (3)
O2A—C1A—C6A—C7A2.9 (4)O2C—C1C—C6C—C7C−2.2 (4)
C2A—C1A—C6A—C7A−177.8 (2)C2C—C1C—C6C—C7C176.3 (2)
C4A—C5A—C6A—C1A−1.2 (4)C4C—C5C—C6C—C1C−0.1 (4)
C4A—C5A—C6A—C7A178.0 (3)C4C—C5C—C6C—C7C−179.1 (2)
C8A—N1A—C7A—C6A179.5 (2)C8C—N1C—C7C—C6C177.5 (2)
C1A—C6A—C7A—N1A−1.1 (4)C1C—C6C—C7C—N1C−1.2 (4)
C5A—C6A—C7A—N1A179.7 (2)C5C—C6C—C7C—N1C177.8 (2)
C7A—N1A—C8A—C13A−161.8 (2)C7C—N1C—C8C—C9C−35.0 (3)
C7A—N1A—C8A—C9A17.8 (4)C7C—N1C—C8C—C13C148.5 (2)
C13A—C8A—C9A—C10A1.6 (4)C13C—C8C—C9C—C10C−0.2 (4)
N1A—C8A—C9A—C10A−177.9 (2)N1C—C8C—C9C—C10C−176.6 (2)
C8A—C9A—C10A—C21E−174.3 (10)C8C—C9C—C10C—C11C1.4 (4)
C8A—C9A—C10A—C11A−1.1 (4)C8C—C9C—C10C—C21G−167.9 (6)
C21E—C10A—C11A—C12A174.3 (8)C9C—C10C—C11C—C12C−1.3 (4)
C9A—C10A—C11A—C12A−0.4 (4)C21G—C10C—C11C—C12C169.7 (6)
C21E—C10A—C11A—C21A−6.2 (8)C9C—C10C—C11C—C21C174.2 (3)
C9A—C10A—C11A—C21A179.1 (2)C21G—C10C—C11C—C21C−14.7 (6)
C10A—C11A—C12A—C13A1.4 (4)C10C—C11C—C12C—C13C0.0 (4)
C21A—C11A—C12A—C13A−178.1 (2)C21C—C11C—C12C—C13C−175.4 (3)
C9A—C8A—C13A—C12A−0.6 (4)C11C—C12C—C13C—C8C1.2 (4)
N1A—C8A—C13A—C12A178.9 (2)C11C—C12C—C13C—N2C−176.8 (2)
C9A—C8A—C13A—N2A179.1 (2)C9C—C8C—C13C—C12C−1.1 (3)
N1A—C8A—C13A—N2A−1.3 (3)N1C—C8C—C13C—C12C175.5 (2)
C11A—C12A—C13A—C8A−0.9 (4)C9C—C8C—C13C—N2C177.0 (2)
C11A—C12A—C13A—N2A179.4 (2)N1C—C8C—C13C—N2C−6.4 (3)
C14A—N2A—C13A—C8A164.4 (2)C14C—N2C—C13C—C12C10.5 (4)
C14A—N2A—C13A—C12A−15.9 (4)C14C—N2C—C13C—C8C−167.6 (2)
C13A—N2A—C14A—C15A179.0 (2)C13C—N2C—C14C—C15C179.7 (2)
N2A—C14A—C15A—C16A−177.8 (2)N2C—C14C—C15C—C16C178.5 (2)
N2A—C14A—C15A—C20A2.2 (4)N2C—C14C—C15C—C20C0.4 (4)
C14A—C15A—C16A—C17A−179.7 (2)C14C—C15C—C16C—C17C−177.3 (2)
C20A—C15A—C16A—C17A0.2 (4)C20C—C15C—C16C—C17C0.8 (4)
C15A—C16A—C17A—C18A1.2 (4)C15C—C16C—C17C—C18C0.4 (4)
C16A—C17A—C18A—C19A−0.7 (4)C16C—C17C—C18C—C19C−1.2 (4)
C17A—C18A—C19A—O4A179.1 (3)C17C—C18C—C19C—O4C179.5 (2)
C17A—C18A—C19A—C20A−1.3 (4)C17C—C18C—C19C—C20C0.8 (4)
C18A—C19A—C20A—O3A−177.4 (3)C14C—C15C—C20C—O3C−2.2 (4)
O4A—C19A—C20A—O3A2.2 (4)C16C—C15C—C20C—O3C179.6 (2)
C18A—C19A—C20A—C15A2.7 (4)C14C—C15C—C20C—C19C177.0 (2)
O4A—C19A—C20A—C15A−177.8 (2)C16C—C15C—C20C—C19C−1.1 (3)
C14A—C15A—C20A—O3A−2.1 (4)C18C—C19C—C20C—O3C179.6 (2)
C16A—C15A—C20A—O3A178.0 (2)O4C—C19C—C20C—O3C0.8 (3)
C14A—C15A—C20A—C19A177.9 (2)C18C—C19C—C20C—C15C0.3 (3)
C16A—C15A—C20A—C19A−2.1 (4)O4C—C19C—C20C—C15C−178.4 (2)
O2B—C1B—C2B—O1B0.9 (3)O2D—C1D—C2D—O1D0.0 (3)
C6B—C1B—C2B—O1B−179.0 (2)C6D—C1D—C2D—O1D−178.9 (2)
O2B—C1B—C2B—C3B−177.3 (2)O2D—C1D—C2D—C3D−179.1 (2)
C6B—C1B—C2B—C3B2.8 (3)C6D—C1D—C2D—C3D2.0 (3)
O1B—C2B—C3B—C4B179.6 (2)O1D—C2D—C3D—C4D−178.4 (2)
C1B—C2B—C3B—C4B−2.2 (4)C1D—C2D—C3D—C4D0.7 (4)
C2B—C3B—C4B—C5B0.2 (4)C2D—C3D—C4D—C5D−2.0 (4)
C3B—C4B—C5B—C6B1.2 (4)C3D—C4D—C5D—C6D0.6 (4)
O2B—C1B—C6B—C5B178.6 (2)O2D—C1D—C6D—C5D177.8 (2)
C2B—C1B—C6B—C5B−1.5 (3)C2D—C1D—C6D—C5D−3.4 (3)
O2B—C1B—C6B—C7B0.3 (4)O2D—C1D—C6D—C7D−6.5 (4)
C2B—C1B—C6B—C7B−179.8 (2)C2D—C1D—C6D—C7D172.2 (2)
C4B—C5B—C6B—C1B−0.5 (3)C4D—C5D—C6D—C1D2.1 (4)
C4B—C5B—C6B—C7B177.8 (2)C4D—C5D—C6D—C7D−173.6 (2)
C8B—N1B—C7B—C6B175.9 (2)C8D—N1D—C7D—C6D−176.6 (2)
C1B—C6B—C7B—N1B−0.4 (4)C1D—C6D—C7D—N1D−2.2 (4)
C5B—C6B—C7B—N1B−178.7 (2)C5D—C6D—C7D—N1D173.4 (2)
C7B—N1B—C8B—C9B−29.9 (3)C7D—N1D—C8D—C9D−37.0 (4)
C7B—N1B—C8B—C13B151.4 (2)C7D—N1D—C8D—C13D144.6 (2)
C13B—C8B—C9B—C10B−1.4 (3)C13D—C8D—C9D—C10D−1.7 (4)
N1B—C8B—C9B—C10B179.9 (2)N1D—C8D—C9D—C10D180.0 (2)
C8B—C9B—C10B—C11B1.8 (4)C8D—C9D—C10D—C11D0.4 (4)
C8B—C9B—C10B—C21F−147.3 (17)C8D—C9D—C10D—C21H−169 (5)
C9B—C10B—C11B—C12B−0.7 (4)C9D—C10D—C11D—C12D0.5 (4)
C21F—C10B—C11B—C12B159.6 (11)C21H—C10D—C11D—C12D175 (2)
C9B—C10B—C11B—C21B178.9 (2)C9D—C10D—C11D—C21D−178.8 (3)
C21F—C10B—C11B—C21B−20.8 (11)C21H—C10D—C11D—C21D−4(2)
C10B—C11B—C12B—C13B−0.6 (3)C10D—C11D—C12D—C13D0.0 (4)
C21B—C11B—C12B—C13B179.8 (2)C21D—C11D—C12D—C13D179.3 (2)
C11B—C12B—C13B—C8B0.9 (3)C11D—C12D—C13D—C8D−1.3 (4)
C11B—C12B—C13B—N2B−177.2 (2)C11D—C12D—C13D—N2D178.2 (2)
C9B—C8B—C13B—C12B0.1 (3)C9D—C8D—C13D—C12D2.2 (4)
N1B—C8B—C13B—C12B178.9 (2)N1D—C8D—C13D—C12D−179.4 (2)
C9B—C8B—C13B—N2B178.3 (2)C9D—C8D—C13D—N2D−177.4 (2)
N1B—C8B—C13B—N2B−2.9 (3)N1D—C8D—C13D—N2D1.1 (3)
C14B—N2B—C13B—C12B4.6 (4)C14D—N2D—C13D—C12D−3.8 (4)
C14B—N2B—C13B—C8B−173.6 (2)C14D—N2D—C13D—C8D175.8 (2)
C13B—N2B—C14B—C15B176.3 (2)C13D—N2D—C14D—C15D−177.5 (2)
N2B—C14B—C15B—C16B−179.0 (2)N2D—C14D—C15D—C16D−179.9 (2)
N2B—C14B—C15B—C20B−1.4 (3)N2D—C14D—C15D—C20D−0.5 (4)
C14B—C15B—C16B—C17B177.6 (2)C14D—C15D—C16D—C17D179.2 (2)
C20B—C15B—C16B—C17B0.0 (4)C20D—C15D—C16D—C17D−0.2 (4)
C15B—C16B—C17B—C18B0.4 (4)C15D—C16D—C17D—C18D0.5 (4)
C16B—C17B—C18B—C19B−0.5 (4)C16D—C17D—C18D—C19D0.2 (4)
C17B—C18B—C19B—O4B−179.6 (2)C17D—C18D—C19D—O4D179.2 (2)
C17B—C18B—C19B—C20B0.2 (4)C17D—C18D—C19D—C20D−1.2 (4)
C18B—C19B—C20B—O3B−178.7 (2)C14D—C15D—C20D—O3D−0.2 (4)
O4B—C19B—C20B—O3B1.1 (3)C16D—C15D—C20D—O3D179.2 (2)
C18B—C19B—C20B—C15B0.2 (3)C14D—C15D—C20D—C19D179.8 (2)
O4B—C19B—C20B—C15B180.0 (2)C16D—C15D—C20D—C19D−0.8 (3)
C14B—C15B—C20B—O3B0.9 (3)C18D—C19D—C20D—O3D−178.5 (2)
C16B—C15B—C20B—O3B178.5 (2)O4D—C19D—C20D—O3D1.1 (3)
C14B—C15B—C20B—C19B−177.9 (2)C18D—C19D—C20D—C15D1.5 (3)
C16B—C15B—C20B—C19B−0.3 (3)O4D—C19D—C20D—C15D−178.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2A—H2OA···N1A0.92 (3)1.86 (3)2.686 (3)149 (3)
O2B—H2OB···N1B0.96 (3)1.82 (3)2.671 (2)146 (2)
O2C—H2OC···N1C0.99 (3)1.72 (3)2.634 (3)151 (3)
O2D—H2OD···N1D0.95 (3)1.81 (3)2.652 (3)147 (3)
N2A—H2NA···O3A0.92 (3)1.86 (3)2.631 (3)140 (2)
N2B—H2NB···O3B1.03 (3)1.70 (3)2.596 (2)144 (3)
N2C—H2NC···O3C0.95 (3)1.83 (2)2.620 (3)139 (2)
N2D—H2ND···O3D0.97 (3)1.80 (3)2.624 (2)140 (2)
O1C—H1OC···O3D0.88 (3)1.91 (4)2.734 (3)155 (3)
O1D—H1OD···O3C0.91 (3)1.93 (3)2.724 (2)146 (3)
O4C—H4OC···O2D0.88 (4)2.48 (4)3.079 (3)126 (3)
O4C—H4OC···O3D0.88 (4)2.31 (4)3.026 (2)138 (3)
O4D—H4OD···O2C0.85 (3)2.34 (3)2.942 (2)129 (3)
O4D—H4OD···O3C0.85 (3)2.29 (3)2.943 (3)134 (3)
O1A—H1OA···O3Bi0.89 (3)1.88 (3)2.732 (2)160 (3)
O1B—H1OB···O3Aii0.85 (3)2.01 (3)2.809 (3)157 (3)
O4A—H4OA···O2Bi0.81 (4)2.25 (4)2.929 (3)142 (4)
O4B—H4OB···O2Aii0.91 (4)2.33 (3)3.021 (3)133 (3)
O4B—H4OB···O3Aii0.91 (4)2.53 (4)3.231 (3)134 (3)
C5B—H5BA···O1Diii0.932.523.372 (3)152
C7B—H7BA···O1Diii0.932.573.416 (3)151
C14A—H14A···O4Div0.932.363.281 (3)170
C14B—H14B···O1Civ0.932.403.260 (3)154
C14C—H14C···O4Bv0.932.463.323 (3)154
C10D—H10D···Cg1vi0.932.973.623 (3)128
C9A—H9AA···Cg2vii0.932.973.716 (3)138
C9C—H9CA···Cg30.932.653.480 (3)148
C21C—H21I···Cg4v0.962.953.696 (4)136
C4B—H4BA···Cg5viii0.932.833.573 (3)138
C17D—H17D···Cg6ix0.932.693.450 (3)139

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2856).

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