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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o981–o982.
Published online 2009 April 8. doi:  10.1107/S160053680901232X
PMCID: PMC2977677

Ethyl 4-(2,4-difluoro­phen­yl)-6-methyl-1-phenyl-2-thioxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Abstract

The asymmetric unit of the title compound, C20H18F2N2O2S, contains four independent mol­ecules, two of which are paired into a dimer by way of two N—H(...)S hydrogen bonds. The other two independent mol­ecules are paired into two centrosymmetric dimers via pairs of inter­molecular N—H(...)S hydrogen bonds. In one mol­ecule, the carboxyl­ate O atoms, methyl­ene and methyl groups attached to the benzene ring are disordered between two positions in a 0.908 (3):0.092 (3) ratio. In two of the independent mol­ecules, the F and H atoms of the diflourophenyl ring are flip-flop disordered (i.e. by 180° about the C—C bond axis linking the ring to the rest of the molecule) in a 3:2 ratio. The crystal packing is stabilized by weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For details of the synthesis, see: Kalluraya & Rai (2003 [triangle]); Kappe (1993 [triangle]); Steele et al. (1998 [triangle]). For the pharmaceutical applications of pyrimidine derivatives, see: Atwal (1990 [triangle]); Manjula et al. (2004 [triangle]); Sadanandam et al. (1992 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For ring puckering analysis, see: Cremer & Pople (1975 [triangle]). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

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Object name is e-65-0o981-scheme1.jpg

Experimental

Crystal data

  • C20H18F2N2O2S
  • M r = 388.42
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o981-efi1.jpg
  • a = 11.3019 (2) Å
  • b = 13.9550 (2) Å
  • c = 24.3463 (4) Å
  • α = 98.807 (1)°
  • β = 93.776 (1)°
  • γ = 102.506 (1)°
  • V = 3684.98 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 100 K
  • 0.57 × 0.36 × 0.14 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.888, T max = 0.971
  • 76910 measured reflections
  • 21361 independent reflections
  • 14585 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.133
  • S = 1.02
  • 21361 reflections
  • 1034 parameters
  • 105 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.33 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/S160053680901232X/cv2538sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901232X/cv2538Isup2.hkl

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

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

The subject of organic solid-state reactivity is a fascinating frontier area of research in the context of green chemistry. Michael addition followed by aldol condensation known as the Robinson's annulation is synthetically a very useful reaction for the construction of six membered cyclic compounds. (Kalluraya & Rai, 2003). 3,4-Dihydro-pyrimidinones are the compounds that have been drawn wide-spread attention, due to their pharmaceutical applications. (Atwal, 1990; Sadanandam et al., 1992). The common synthetic routes to these compounds generally involve multi-step transformation that are essentially based on the Biginelli condensation methodology (Steele et al., 1998). These pyrimidinones are also associated with activities like calcium channel blocking (Manjula et al., 2004). In 1893, Biginelli reported the first synthesis of dihydropyrimidines by a simple one-pot condensation reaction of ethyl acetoacetate, benzaldehyde and urea. In the following decades the original cyclo-condensation reaction has been extended widely to include variations in all three components, allowing access to a large number of muti functionalized dihydropyrimidinone derivatives (Kappe, 1993). Due to the above interests, we report the synthesis of title compound (I) by means of Robinson's annulation employing microwave technique and its crystal structure.

The asymmetric unit of the title compound (Fig 1) contains four crystallographically independent molecules (A, B, C & D) with two molecules (C and D) exhibiting similar geometries and the other two molecules (A and B) displaying disorder. The bond lengths (Allen et al., 1987) and angles are found to have normal values. Molecules A and B are linked together via intramolecular N—H···S hydrogen bonds into pseudo-centrosymmetric dimers whereas individual molecules C (and also D) are each linked via interamolecular N—H···S hydrogen bonds into centrosymmetric dimers. The pyrimidine ring exhibits non planarity with the maximum deviation of -0.1570 (19)Å for atom C9A, 0.1531 (19)Å for atom C9B, 0.1285 (16)Å for atom N2C and 0.1275 (16)Å for atom N2D. The pyrimidine rings of molecule A adopt the boat conformation with puckering parameters Q = 0.2403 (17) Å, θ = 75.0 (4)°, [var phi] = 191.0 (4)°; molecule B and D adopting the twisted boat conformation with the puckering parameters Q = 0.2328 (17) Å, θ=107.7 (4)°, [var phi]=14.1 (5)°; Q=0.2027 (17) Å, θ=111.1 (5) Å, [var phi]=33.5 (5)° respectively; whereas molecule C adopting the screw boat conformation with the puckering parameters Q =0.1999 (17) Å, θ = 69.6 (5)°, [var phi] = 217.6 (5)° (Cremer & Pople, 1975). The pyrimidine rings are almost orthogonal to the attached benzene rings in molecules A, B & D forming dihedral angles of 82.90 (8)° (N1A–N2A/C7A–C10A; C1A–C6A) and 87.22 (7)° (N1A–N2A/C7A–C10A; C11A–C16A); 88.76 (8)° (N1B–N2B/C7B–C10B; C1B–C6B) and 88.05 (7)° (N1B–N2B/C7B–C10B; C11B–C16B); and 83.53 (7)° N1D–N2D/C7D–C10D; C1D–C6D) and 81.68 (6)° (N1D–N2D/C7D–C10D; C11D–C16D) respectively. In molecule C, the pyrimidine ring forms dihedral angles of 68.65 (8)° (N1C–N2C/C7C–C10C; C1C–C6C) and 82.81 (8)° (N1C–N2C/C7C–C10C; C11C–C16C) with the attached benzene rings. In molecule A, the carboxylate oxygen, methylene and methyl groups (O1A/C18A/C19A) are disordered with occupancies of 0.908 (3):0.092 (3). The atoms F1A:H16C and H12A:F3A are flip-flop disordered with occupancies of 0.618 (3):0.382 (3). In molecule B, the atoms F1B:H16D and H12B:F3B are flip-flop disordered with occupancies of 0.382 (3):0.618 (3).

The crystal packing is stabilized by intermolecular C—H···O and N—H···S hydrogen bonding (Table 1).

Experimental

A mixture of 2,4-difluoro benzaldehyde (0.01 mol), ethyl acetoacetate (0.015 mol), phenyl thiourea (0.01 mol) and conc. H2SO4 (2 drops) in absolute alcohol (10 ml) taken in a beaker (100 ml) was zapped inside a MW oven for a duration of three minutes (at 160 Watt). The reaction mixture was then allowed to stand at room temperature and the product formed was filtered, washed with ethanol followed by water and dried. Further purification was done by recrystallization from ethanol (yield 77%). Crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.

Refinement

H atoms were positioned geometrically [C–H = 0.93–0.98Å (aromatic, methylene) or 0.96Å (methyl)] and refined using a riding model, with Uiso(H) = 1.2Ueq(aromatic C, methylene) and 1.5Ueq(methyl C). A rotating–group model was used for the methyl groups. The N bound hydrogen atoms were located from the Fourier map and isotropically refined with the bond restraint N—H = 0.88 (2) Å. In molecule A the carboxylate oxygen, methylene and methyl groups (O1A/C18A/C19A) are disordered with occupancies of 0.902 (3):0.098 (3). The atoms F1A:H16C and H12A:F3A are flip-flop disordered with occupancies of 0.618 (3):0.382 (3). In molecule B, the atoms F1B:H16D and H12B:F3B are flip-flop disordered with the occupancies of 0.382 (3):0.618 (3). During the data collection, the temperature was controlled according to the literature procedure (Cosier & Glazer, 1986).

Figures

Fig. 1.
The content of asymmetric unit of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 20% probability level.

Crystal data

C20H18F2N2O2SZ = 8
Mr = 388.42F(000) = 1616
Triclinic, P1Dx = 1.400 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.3019 (2) ÅCell parameters from 9848 reflections
b = 13.9550 (2) Åθ = 2.1–32.6°
c = 24.3463 (4) ŵ = 0.21 mm1
α = 98.807 (1)°T = 100 K
β = 93.776 (1)°Block, colourless
γ = 102.506 (1)°0.57 × 0.36 × 0.14 mm
V = 3684.98 (10) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer21361 independent reflections
Radiation source: fine-focus sealed tube14585 reflections with I > 2σ(I)
graphiteRint = 0.038
[var phi] and ω scansθmax = 30.0°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −15→15
Tmin = 0.888, Tmax = 0.971k = −19→19
76910 measured reflectionsl = −34→34

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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0548P)2 + 1.336P] where P = (Fo2 + 2Fc2)/3
21361 reflections(Δ/σ)max < 0.002
1034 parametersΔρmax = 0.47 e Å3
105 restraintsΔρmin = −0.33 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)
S1A0.75838 (4)0.19688 (3)0.160405 (18)0.02552 (10)
O2A0.88227 (12)0.68085 (9)0.25523 (5)0.0299 (3)
F2A1.32384 (11)0.55763 (8)0.35317 (5)0.0408 (3)
N1A0.82419 (13)0.37625 (10)0.12983 (5)0.0210 (3)
N2A0.79954 (14)0.37477 (10)0.22300 (6)0.0228 (3)
C1A0.73542 (17)0.28783 (13)0.03654 (7)0.0297 (4)
H1AA0.65800.28800.04730.036*
C2A0.74994 (19)0.25026 (15)−0.01824 (8)0.0372 (5)
H2AA0.68200.2259−0.04440.045*
C3A0.8645 (2)0.24892 (14)−0.03401 (7)0.0355 (5)
H3AA0.87380.2235−0.07070.043*
C4A0.96586 (19)0.28542 (15)0.00479 (7)0.0333 (4)
H4AA1.04320.2845−0.00590.040*
C5A0.95199 (16)0.32340 (13)0.05967 (7)0.0256 (4)
H5AA1.01970.34750.08590.031*
C6A0.83664 (15)0.32491 (11)0.07489 (6)0.0199 (3)
C7A0.83666 (15)0.48118 (11)0.13756 (7)0.0205 (3)
C8A0.84716 (15)0.53280 (11)0.18996 (6)0.0203 (3)
C9A0.85118 (16)0.48197 (12)0.24026 (6)0.0217 (3)
H9AA0.79900.50810.26650.026*
C10A0.79674 (15)0.32235 (12)0.17234 (7)0.0209 (3)
C11A0.97837 (16)0.50213 (11)0.27052 (6)0.0224 (3)
C12A1.07877 (17)0.48994 (14)0.24264 (7)0.0293 (4)
H12A1.06700.46820.20420.035*0.618 (3)
F1A1.0585 (2)0.4410 (2)0.19055 (10)0.0277 (8)0.382 (3)
C13A1.19565 (18)0.50857 (14)0.26922 (8)0.0325 (4)
H13A1.26140.50030.24940.039*
C14A1.21032 (17)0.53975 (12)0.32601 (8)0.0297 (4)
C15A1.11583 (19)0.55307 (13)0.35638 (7)0.0312 (4)
H15A1.12840.57410.39490.037*
C16A1.00078 (18)0.53433 (12)0.32796 (7)0.0275 (4)
H16C0.93590.54360.34810.033*0.382 (3)
F3A0.90942 (17)0.54105 (14)0.35765 (7)0.0382 (6)0.618 (3)
C17A0.86280 (16)0.64179 (12)0.20659 (7)0.0245 (3)
O1A0.86007 (18)0.69379 (10)0.16543 (5)0.0275 (4)0.908 (3)
C18A0.8829 (2)0.80187 (14)0.18231 (8)0.0290 (5)0.908 (3)
H18A0.96470.82810.20090.035*0.908 (3)
H18B0.82520.81900.20770.035*0.908 (3)
C19A0.8681 (2)0.84402 (16)0.12969 (9)0.0333 (5)0.908 (3)
H19A0.88200.91520.13880.050*0.908 (3)
H19B0.78700.81710.11170.050*0.908 (3)
H19C0.92590.82660.10500.050*0.908 (3)
O1E0.7873 (18)0.6727 (9)0.1611 (6)0.0275 (4)0.092 (3)
C18E0.797 (2)0.7800 (11)0.1680 (9)0.030 (4)0.092 (3)
H18I0.72420.79320.15020.036*0.092 (3)
H18J0.80450.80810.20750.036*0.092 (3)
C19E0.905 (2)0.8257 (16)0.1425 (10)0.0333 (5)0.092 (3)
H19M0.90650.89480.14240.050*0.092 (3)
H19N0.90150.79200.10470.050*0.092 (3)
H19O0.97730.82020.16350.050*0.092 (3)
C20A0.83525 (18)0.52424 (13)0.08446 (7)0.0277 (4)
H20A0.83480.59360.09320.041*
H20B0.76360.48960.06010.041*
H20C0.90640.51700.06630.041*
S1B0.75338 (4)0.28831 (3)0.347157 (17)0.02507 (10)
O1B0.65299 (12)−0.20878 (8)0.34331 (5)0.0276 (3)
O2B0.62896 (12)−0.19589 (9)0.25299 (5)0.0313 (3)
F2B0.21354 (12)−0.05966 (9)0.14024 (5)0.0551 (4)
N1B0.68304 (13)0.10938 (10)0.37749 (5)0.0201 (3)
N2B0.72065 (14)0.11022 (10)0.28549 (6)0.0234 (3)
C1B0.55091 (15)0.17504 (12)0.44143 (7)0.0231 (3)
H1BA0.48690.15420.41310.028*
C2B0.53163 (17)0.21904 (13)0.49421 (7)0.0278 (4)
H2BA0.45450.22790.50130.033*
C3B0.62774 (19)0.24983 (13)0.53636 (7)0.0308 (4)
H3BA0.61500.27930.57170.037*
C4B0.74210 (18)0.23656 (13)0.52558 (7)0.0304 (4)
H4BA0.80620.25690.55390.037*
C5B0.76198 (16)0.19320 (12)0.47299 (7)0.0252 (4)
H5BA0.83920.18480.46580.030*
C6B0.66595 (15)0.16241 (11)0.43125 (6)0.0189 (3)
C7B0.66750 (14)0.00404 (11)0.37000 (7)0.0200 (3)
C8B0.66290 (15)−0.04792 (11)0.31810 (6)0.0204 (3)
C9B0.66849 (16)0.00325 (12)0.26761 (7)0.0224 (3)
H9BA0.7238−0.02360.24340.027*
C10B0.71625 (15)0.16289 (12)0.33534 (7)0.0205 (3)
C11B0.54581 (16)−0.01458 (12)0.23358 (7)0.0243 (4)
C12B0.44191 (18)−0.00158 (14)0.25786 (8)0.0331 (4)
H12B0.44810.01860.29640.040*0.618 (3)
F1B0.4577 (2)0.0489 (2)0.30888 (10)0.0306 (8)0.382 (3)
C13B0.32909 (19)−0.01707 (15)0.22775 (9)0.0391 (5)
H13B0.2606−0.00850.24530.047*
C14B0.3225 (2)−0.04555 (13)0.17092 (8)0.0383 (5)
C15B0.4209 (2)−0.05954 (14)0.14403 (8)0.0410 (5)
H15B0.4140−0.07880.10540.049*
C16B0.53175 (19)−0.04414 (13)0.17595 (7)0.0321 (4)
H16D0.5994−0.05400.15800.039*0.382 (3)
F3B0.62696 (19)−0.05051 (14)0.14996 (7)0.0416 (6)0.618 (3)
C17B0.64673 (15)−0.15711 (12)0.30179 (7)0.0229 (3)
C18B0.63071 (18)−0.31692 (12)0.32629 (7)0.0300 (4)
H18C0.6890−0.33350.30100.036*
H18D0.5493−0.34310.30730.036*
C19B0.64424 (19)−0.36055 (14)0.37831 (8)0.0358 (4)
H19D0.6324−0.43150.36850.054*
H19E0.5846−0.34530.40250.054*
H19F0.7244−0.33280.39720.054*
C20B0.65746 (17)−0.03903 (12)0.42309 (7)0.0254 (4)
H20D0.6340−0.11040.41400.038*
H20E0.5972−0.01480.44370.038*
H20F0.7348−0.01930.44540.038*
S1C0.92583 (4)0.83676 (3)0.468491 (17)0.02691 (10)
O1C0.92847 (12)0.84445 (10)0.74524 (5)0.0323 (3)
O2C1.04966 (12)0.99326 (9)0.74164 (5)0.0315 (3)
F1C0.74070 (9)0.91926 (7)0.58298 (4)0.0306 (2)
F2C0.65175 (11)1.21670 (9)0.66815 (5)0.0391 (3)
N1C0.91419 (13)0.77793 (10)0.56803 (6)0.0214 (3)
N2C0.99707 (13)0.94456 (10)0.56861 (6)0.0211 (3)
C1C0.9145 (2)0.62030 (13)0.50690 (8)0.0337 (4)
H1CA0.99700.64300.50380.040*
C2C0.8524 (3)0.52555 (15)0.48020 (9)0.0495 (6)
H2CA0.89340.48570.45810.059*
C3C0.7326 (3)0.49036 (17)0.48598 (11)0.0642 (8)
H3CA0.69240.42660.46840.077*
C4C0.6715 (3)0.5496 (2)0.51788 (13)0.0709 (9)
H4CA0.59000.52520.52240.085*
C5C0.73056 (19)0.64611 (17)0.54357 (10)0.0471 (6)
H5CA0.68830.68690.56410.057*
C6C0.85196 (16)0.68006 (12)0.53807 (7)0.0257 (4)
C7C0.93441 (15)0.79305 (12)0.62721 (7)0.0212 (3)
C8C0.96774 (15)0.88628 (12)0.65661 (7)0.0214 (3)
C9C0.99104 (15)0.97668 (12)0.62817 (6)0.0199 (3)
H9CA1.07151.01770.64370.024*
C10C0.94492 (15)0.85531 (12)0.53858 (7)0.0207 (3)
C11C0.89957 (15)1.04126 (12)0.63833 (6)0.0202 (3)
C12C0.77895 (15)1.01087 (12)0.61542 (7)0.0226 (3)
C13C0.69455 (16)1.06869 (13)0.62349 (7)0.0271 (4)
H13C0.61501.04720.60650.033*
C14C0.73425 (17)1.16003 (13)0.65805 (7)0.0276 (4)
C15C0.85183 (17)1.19531 (13)0.68213 (7)0.0274 (4)
H15C0.87591.25750.70490.033*
C17C0.98855 (16)0.91343 (13)0.71814 (7)0.0244 (3)
C18C0.9448 (2)0.86862 (15)0.80605 (7)0.0372 (5)
H18E0.90320.92040.81910.045*
H18F1.03060.89170.81940.045*
C19C0.8910 (2)0.77396 (18)0.82669 (9)0.0488 (6)
H19G0.89570.78680.86670.073*
H19H0.93580.72460.81500.073*
H19I0.80740.75010.81150.073*
C20C0.92231 (17)0.69861 (12)0.65126 (7)0.0276 (4)
H20G0.96660.71320.68770.041*
H20H0.95470.65150.62730.041*
H20I0.83790.67100.65410.041*
S1D0.56431 (4)0.66307 (3)1.034717 (17)0.02846 (10)
O1D0.56232 (13)0.66675 (10)0.75837 (5)0.0343 (3)
O2D0.43475 (12)0.52084 (10)0.76128 (5)0.0335 (3)
F2D0.83022 (11)0.28243 (9)0.83084 (5)0.0396 (3)
F1D0.75066 (9)0.58129 (8)0.91963 (4)0.0316 (2)
N1D0.58169 (13)0.72586 (10)0.93662 (5)0.0212 (3)
N2D0.49398 (13)0.55931 (10)0.93340 (6)0.0215 (3)
C1D0.59595 (18)0.88982 (13)0.99457 (7)0.0305 (4)
H1DA0.51140.87810.99200.037*
C2D0.6675 (2)0.97884 (14)1.02477 (8)0.0374 (5)
H2DA0.63051.02691.04230.045*
C3D0.7924 (2)0.99603 (15)1.02882 (9)0.0437 (5)
H3DA0.83961.05621.04820.052*
C4D0.8475 (2)0.92390 (16)1.00414 (9)0.0436 (5)
H4DA0.93190.93441.00810.052*
C5D0.77699 (17)0.83532 (14)0.97322 (8)0.0327 (4)
H5DA0.81410.78720.95580.039*
C6D0.65208 (15)0.81957 (12)0.96858 (7)0.0223 (3)
C7D0.56196 (15)0.71469 (12)0.87761 (7)0.0215 (3)
C8D0.52512 (15)0.62249 (12)0.84687 (7)0.0219 (3)
C9D0.50040 (15)0.53038 (11)0.87357 (6)0.0204 (3)
H9DA0.41960.49070.85750.024*
C10D0.54763 (15)0.64690 (12)0.96469 (7)0.0211 (3)
C11D0.59026 (15)0.46450 (11)0.86199 (6)0.0203 (3)
C12D0.71052 (15)0.49119 (12)0.88551 (7)0.0235 (3)
C13D0.79177 (17)0.43117 (13)0.87703 (7)0.0282 (4)
H13D0.87090.45020.89460.034*
C14D0.75037 (17)0.34137 (13)0.84127 (7)0.0287 (4)
C15D0.63312 (17)0.30988 (13)0.81591 (7)0.0274 (4)
H15D0.60780.24890.79210.033*
C16C0.93428 (16)1.13519 (12)0.67144 (7)0.0232 (3)
H16A1.01481.15860.68690.028*
C17D0.50025 (16)0.59825 (13)0.78517 (7)0.0257 (4)
C18D0.5410 (2)0.64679 (16)0.69772 (7)0.0406 (5)
H18G0.45440.62720.68570.049*
H18H0.57870.59380.68240.049*
C19D0.5972 (3)0.7420 (2)0.67881 (9)0.0572 (7)
H19J0.58750.73250.63870.086*
H19K0.68240.76130.69190.086*
H19L0.55780.79330.69370.086*
C20D0.57818 (18)0.81196 (12)0.85654 (7)0.0281 (4)
H20J0.54950.79960.81750.042*
H20K0.66290.84510.86170.042*
H20L0.53250.85330.87700.042*
C16D0.55333 (16)0.37216 (12)0.82703 (7)0.0235 (3)
H16B0.47330.35160.81070.028*
H1NA0.777 (2)0.3407 (16)0.2484 (9)0.042 (6)*
H1NB0.7418 (18)0.1428 (15)0.2587 (8)0.031 (5)*
H1NC1.0197 (19)0.9954 (16)0.5500 (8)0.037 (6)*
H1ND0.4711 (18)0.5074 (15)0.9495 (8)0.031 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1A0.0325 (2)0.01602 (19)0.0260 (2)0.00129 (17)0.00659 (17)0.00182 (15)
O2A0.0411 (8)0.0207 (6)0.0250 (6)0.0053 (5)0.0032 (5)−0.0019 (5)
F2A0.0426 (7)0.0315 (6)0.0428 (7)0.0079 (5)−0.0182 (5)0.0001 (5)
N1A0.0281 (8)0.0162 (6)0.0171 (6)0.0028 (6)0.0038 (5)0.0005 (5)
N2A0.0293 (8)0.0172 (7)0.0208 (7)0.0013 (6)0.0070 (6)0.0033 (5)
C1A0.0258 (9)0.0293 (9)0.0291 (9)0.0025 (7)−0.0010 (7)−0.0037 (7)
C2A0.0433 (12)0.0343 (10)0.0258 (9)0.0030 (9)−0.0084 (8)−0.0064 (8)
C3A0.0594 (14)0.0290 (10)0.0195 (8)0.0155 (9)0.0059 (8)0.0003 (7)
C4A0.0418 (11)0.0415 (11)0.0245 (9)0.0209 (9)0.0122 (8)0.0100 (8)
C5A0.0262 (9)0.0303 (9)0.0213 (8)0.0079 (7)0.0011 (7)0.0061 (7)
C6A0.0261 (9)0.0153 (7)0.0166 (7)0.0032 (6)0.0007 (6)−0.0001 (6)
C7A0.0226 (8)0.0154 (7)0.0226 (8)0.0032 (6)0.0024 (6)0.0022 (6)
C8A0.0229 (8)0.0172 (7)0.0198 (7)0.0028 (6)0.0030 (6)0.0021 (6)
C9A0.0286 (9)0.0169 (7)0.0186 (7)0.0034 (7)0.0071 (6)0.0007 (6)
C10A0.0202 (8)0.0186 (8)0.0228 (8)0.0021 (6)0.0038 (6)0.0022 (6)
C11A0.0316 (9)0.0146 (7)0.0194 (8)0.0018 (7)0.0025 (7)0.0029 (6)
C12A0.0321 (10)0.0310 (9)0.0218 (8)0.0058 (8)0.0018 (7)−0.0023 (7)
F1A0.0273 (15)0.0395 (17)0.0143 (12)0.0068 (12)0.0003 (10)0.0008 (11)
C13A0.0298 (10)0.0342 (10)0.0322 (10)0.0091 (8)−0.0004 (8)0.0012 (8)
C14A0.0361 (11)0.0184 (8)0.0311 (9)0.0024 (7)−0.0100 (8)0.0045 (7)
C15A0.0496 (12)0.0199 (8)0.0199 (8)0.0018 (8)−0.0051 (8)0.0030 (6)
C16A0.0405 (11)0.0196 (8)0.0197 (8)0.0017 (7)0.0049 (7)0.0023 (6)
F3A0.0459 (12)0.0459 (12)0.0211 (9)0.0097 (9)0.0133 (8)−0.0025 (7)
C17A0.0297 (9)0.0196 (8)0.0244 (8)0.0059 (7)0.0070 (7)0.0023 (6)
O1A0.0434 (11)0.0168 (6)0.0220 (6)0.0071 (7)0.0036 (7)0.0018 (5)
C18A0.0447 (14)0.0155 (9)0.0261 (10)0.0073 (9)0.0068 (9)−0.0008 (7)
C19A0.0486 (15)0.0220 (10)0.0293 (11)0.0073 (9)0.0021 (10)0.0059 (8)
O1E0.0434 (11)0.0168 (6)0.0220 (6)0.0071 (7)0.0036 (7)0.0018 (5)
C18E0.048 (10)0.015 (7)0.032 (9)0.018 (7)0.011 (8)0.004 (7)
C19E0.0486 (15)0.0220 (10)0.0293 (11)0.0073 (9)0.0021 (10)0.0059 (8)
C20A0.0416 (11)0.0218 (8)0.0192 (8)0.0079 (8)0.0005 (7)0.0026 (6)
S1B0.0324 (2)0.01644 (19)0.0247 (2)0.00171 (17)0.00731 (17)0.00205 (15)
O1B0.0398 (7)0.0176 (6)0.0249 (6)0.0085 (5)0.0001 (5)0.0003 (5)
O2B0.0456 (8)0.0214 (6)0.0236 (6)0.0054 (6)0.0024 (5)−0.0029 (5)
F2B0.0644 (9)0.0343 (7)0.0563 (8)0.0086 (6)−0.0389 (7)−0.0011 (6)
N1B0.0250 (7)0.0156 (6)0.0179 (6)0.0026 (5)0.0032 (5)0.0003 (5)
N2B0.0291 (8)0.0182 (7)0.0211 (7)0.0007 (6)0.0075 (6)0.0023 (5)
C1B0.0255 (9)0.0233 (8)0.0210 (8)0.0061 (7)0.0012 (6)0.0054 (6)
C2B0.0327 (10)0.0291 (9)0.0267 (9)0.0134 (8)0.0103 (7)0.0081 (7)
C3B0.0513 (12)0.0234 (9)0.0179 (8)0.0098 (8)0.0063 (8)0.0016 (6)
C4B0.0392 (11)0.0248 (9)0.0222 (8)0.0026 (8)−0.0066 (7)−0.0011 (7)
C5B0.0237 (9)0.0235 (8)0.0259 (8)0.0040 (7)−0.0013 (7)0.0004 (7)
C6B0.0243 (8)0.0147 (7)0.0168 (7)0.0034 (6)0.0026 (6)0.0013 (6)
C7B0.0198 (8)0.0176 (7)0.0217 (8)0.0031 (6)0.0013 (6)0.0024 (6)
C8B0.0205 (8)0.0179 (7)0.0212 (8)0.0025 (6)0.0022 (6)0.0014 (6)
C9B0.0271 (9)0.0170 (7)0.0209 (8)0.0015 (7)0.0061 (7)−0.0003 (6)
C10B0.0206 (8)0.0175 (7)0.0218 (8)0.0020 (6)0.0035 (6)0.0015 (6)
C11B0.0353 (10)0.0166 (8)0.0186 (8)0.0013 (7)0.0013 (7)0.0027 (6)
C12B0.0360 (11)0.0347 (10)0.0252 (9)0.0101 (8)−0.0047 (8)−0.0045 (7)
F1B0.0294 (16)0.0420 (17)0.0199 (14)0.0105 (13)0.0006 (11)0.0006 (11)
C13B0.0363 (11)0.0363 (11)0.0413 (11)0.0104 (9)−0.0094 (9)−0.0010 (9)
C14B0.0507 (13)0.0195 (9)0.0377 (11)0.0027 (8)−0.0219 (10)0.0025 (8)
C15B0.0713 (16)0.0230 (9)0.0209 (9)0.0001 (10)−0.0124 (9)0.0017 (7)
C16B0.0499 (12)0.0222 (9)0.0199 (8)−0.0006 (8)0.0039 (8)0.0028 (7)
F3B0.0603 (14)0.0411 (11)0.0218 (9)0.0099 (10)0.0153 (8)−0.0017 (8)
C17B0.0231 (9)0.0196 (8)0.0251 (8)0.0047 (7)0.0035 (7)0.0009 (6)
C18B0.0422 (11)0.0164 (8)0.0301 (9)0.0060 (8)0.0069 (8)−0.0003 (7)
C19B0.0468 (12)0.0237 (9)0.0353 (10)0.0075 (8)−0.0025 (9)0.0042 (8)
C20B0.0360 (10)0.0209 (8)0.0203 (8)0.0079 (7)0.0023 (7)0.0045 (6)
S1C0.0386 (3)0.0189 (2)0.0221 (2)0.00405 (18)−0.00055 (18)0.00549 (16)
O1C0.0438 (8)0.0327 (7)0.0214 (6)0.0080 (6)0.0025 (5)0.0092 (5)
O2C0.0387 (8)0.0268 (7)0.0277 (6)0.0094 (6)−0.0021 (6)0.0008 (5)
F1C0.0208 (5)0.0248 (5)0.0417 (6)0.0013 (4)−0.0012 (4)−0.0007 (4)
F2C0.0432 (7)0.0407 (7)0.0440 (7)0.0280 (6)0.0102 (5)0.0113 (5)
N1C0.0242 (7)0.0172 (6)0.0225 (7)0.0031 (6)0.0006 (6)0.0050 (5)
N2C0.0233 (7)0.0183 (7)0.0222 (7)0.0035 (6)0.0047 (6)0.0061 (5)
C1C0.0488 (12)0.0181 (8)0.0327 (10)0.0033 (8)0.0033 (9)0.0059 (7)
C2C0.090 (2)0.0185 (9)0.0338 (11)0.0032 (11)−0.0091 (11)0.0056 (8)
C3C0.091 (2)0.0265 (11)0.0571 (15)−0.0170 (13)−0.0361 (15)0.0122 (11)
C4C0.0472 (16)0.0550 (17)0.092 (2)−0.0252 (13)−0.0304 (15)0.0246 (16)
C5C0.0293 (11)0.0454 (13)0.0604 (14)−0.0040 (9)−0.0074 (10)0.0130 (11)
C6C0.0297 (10)0.0177 (8)0.0268 (8)−0.0016 (7)−0.0043 (7)0.0082 (6)
C7C0.0200 (8)0.0219 (8)0.0231 (8)0.0049 (6)0.0016 (6)0.0089 (6)
C8C0.0211 (8)0.0209 (8)0.0238 (8)0.0062 (6)0.0013 (6)0.0069 (6)
C9C0.0192 (8)0.0184 (7)0.0217 (8)0.0033 (6)0.0012 (6)0.0040 (6)
C10C0.0188 (8)0.0198 (8)0.0246 (8)0.0056 (6)0.0025 (6)0.0059 (6)
C11C0.0219 (8)0.0190 (7)0.0212 (8)0.0054 (6)0.0035 (6)0.0070 (6)
C12C0.0231 (9)0.0202 (8)0.0245 (8)0.0034 (7)0.0029 (7)0.0062 (6)
C13C0.0237 (9)0.0308 (9)0.0306 (9)0.0093 (7)0.0048 (7)0.0119 (7)
C14C0.0332 (10)0.0292 (9)0.0292 (9)0.0181 (8)0.0110 (7)0.0135 (7)
C15C0.0373 (10)0.0230 (8)0.0253 (8)0.0117 (8)0.0054 (7)0.0069 (7)
C17C0.0261 (9)0.0243 (8)0.0256 (8)0.0114 (7)−0.0008 (7)0.0067 (7)
C18C0.0513 (13)0.0451 (12)0.0225 (9)0.0248 (10)0.0035 (8)0.0084 (8)
C19C0.0567 (15)0.0683 (16)0.0344 (11)0.0258 (13)0.0153 (10)0.0282 (11)
C20C0.0339 (10)0.0208 (8)0.0305 (9)0.0072 (7)0.0018 (7)0.0114 (7)
S1D0.0427 (3)0.0190 (2)0.0208 (2)0.00048 (18)0.00164 (18)0.00446 (15)
O1D0.0487 (9)0.0343 (7)0.0211 (6)0.0100 (6)0.0015 (6)0.0081 (5)
O2D0.0386 (8)0.0307 (7)0.0279 (7)0.0092 (6)−0.0067 (6)−0.0021 (5)
F2D0.0449 (7)0.0402 (7)0.0433 (7)0.0274 (6)0.0087 (5)0.0094 (5)
F1D0.0228 (5)0.0261 (5)0.0397 (6)0.0011 (4)−0.0038 (4)−0.0036 (4)
N1D0.0254 (8)0.0168 (6)0.0198 (6)0.0014 (6)0.0009 (5)0.0038 (5)
N2D0.0241 (8)0.0167 (7)0.0222 (7)0.0007 (6)0.0033 (6)0.0039 (5)
C1D0.0350 (10)0.0241 (9)0.0319 (9)0.0067 (8)0.0026 (8)0.0033 (7)
C2D0.0558 (14)0.0211 (9)0.0338 (10)0.0081 (9)0.0018 (9)0.0020 (7)
C3D0.0560 (14)0.0212 (9)0.0426 (12)−0.0113 (9)−0.0039 (10)0.0032 (8)
C4D0.0360 (12)0.0374 (12)0.0497 (13)−0.0098 (9)0.0012 (10)0.0107 (10)
C5D0.0312 (10)0.0271 (9)0.0371 (10)−0.0005 (8)0.0064 (8)0.0064 (8)
C6D0.0265 (9)0.0165 (7)0.0217 (8)−0.0001 (6)0.0009 (7)0.0050 (6)
C7D0.0219 (8)0.0218 (8)0.0218 (8)0.0053 (7)0.0022 (6)0.0066 (6)
C8D0.0225 (8)0.0216 (8)0.0223 (8)0.0066 (7)0.0001 (6)0.0048 (6)
C9D0.0197 (8)0.0176 (7)0.0223 (8)0.0017 (6)0.0005 (6)0.0029 (6)
C10D0.0208 (8)0.0177 (8)0.0240 (8)0.0025 (6)0.0019 (6)0.0048 (6)
C11D0.0220 (8)0.0178 (7)0.0215 (8)0.0038 (6)0.0024 (6)0.0058 (6)
C12D0.0232 (9)0.0221 (8)0.0239 (8)0.0025 (7)0.0011 (7)0.0047 (6)
C13D0.0256 (9)0.0314 (9)0.0304 (9)0.0090 (8)0.0030 (7)0.0105 (7)
C14D0.0347 (10)0.0290 (9)0.0296 (9)0.0165 (8)0.0091 (8)0.0115 (7)
C15D0.0385 (11)0.0201 (8)0.0248 (8)0.0085 (7)0.0040 (7)0.0048 (6)
C16C0.0261 (9)0.0203 (8)0.0238 (8)0.0051 (7)0.0025 (7)0.0059 (6)
C17D0.0285 (9)0.0268 (9)0.0242 (8)0.0130 (7)−0.0023 (7)0.0042 (7)
C18D0.0617 (14)0.0494 (12)0.0197 (9)0.0326 (11)0.0018 (9)0.0065 (8)
C19D0.0778 (18)0.0764 (18)0.0364 (12)0.0400 (15)0.0188 (12)0.0311 (12)
C20D0.0376 (10)0.0209 (8)0.0279 (9)0.0083 (7)0.0021 (7)0.0086 (7)
C16D0.0272 (9)0.0196 (8)0.0224 (8)0.0029 (7)0.0003 (7)0.0042 (6)

Geometric parameters (Å, °)

S1A—C10A1.6844 (16)C19B—H19D0.9600
O2A—C17A1.210 (2)C19B—H19E0.9600
F2A—C14A1.358 (2)C19B—H19F0.9600
N1A—C10A1.383 (2)C20B—H20D0.9600
N1A—C7A1.4219 (19)C20B—H20E0.9600
N1A—C6A1.4483 (19)C20B—H20F0.9600
N2A—C10A1.329 (2)S1C—C10C1.6786 (16)
N2A—C9A1.467 (2)O1C—C17C1.339 (2)
N2A—H1NA0.86 (2)O1C—C18C1.458 (2)
C1A—C6A1.380 (2)O2C—C17C1.210 (2)
C1A—C2A1.390 (3)F1C—C12C1.3607 (19)
C1A—H1AA0.9300F2C—C14C1.3585 (19)
C2A—C3A1.377 (3)N1C—C10C1.381 (2)
C2A—H2AA0.9300N1C—C7C1.419 (2)
C3A—C4A1.386 (3)N1C—C6C1.450 (2)
C3A—H3AA0.9300N2C—C10C1.334 (2)
C4A—C5A1.392 (2)N2C—C9C1.462 (2)
C4A—H4AA0.9300N2C—H1NC0.90 (2)
C5A—C6A1.382 (2)C1C—C6C1.380 (3)
C5A—H5AA0.9300C1C—C2C1.392 (3)
C7A—C8A1.350 (2)C1C—H1CA0.9300
C7A—C20A1.507 (2)C2C—C3C1.361 (4)
C8A—C17A1.481 (2)C2C—H2CA0.9300
C8A—C9A1.509 (2)C3C—C4C1.373 (4)
C9A—C11A1.520 (2)C3C—H3CA0.9300
C9A—H9AA0.9800C4C—C5C1.396 (3)
C11A—C12A1.388 (2)C4C—H4CA0.9300
C11A—C16A1.390 (2)C5C—C6C1.374 (3)
C12A—F1A1.325 (3)C5C—H5CA0.9300
C12A—C13A1.385 (3)C7C—C8C1.347 (2)
C12A—H12A0.9300C7C—C20C1.506 (2)
C13A—C14A1.372 (3)C8C—C17C1.478 (2)
C13A—H13A0.9300C8C—C9C1.513 (2)
C14A—C15A1.367 (3)C9C—C11C1.520 (2)
C15A—C16A1.385 (3)C9C—H9CA0.9800
C15A—H15A0.9300C11C—C12C1.388 (2)
C16A—F3A1.310 (2)C11C—C16C1.391 (2)
C16A—H16C0.9300C12C—C13C1.382 (2)
C17A—O1A1.327 (2)C13C—C14C1.381 (3)
C17A—O1E1.523 (15)C13C—H13C0.9300
O1A—C18A1.462 (2)C14C—C15C1.370 (3)
C18A—C19A1.503 (3)C15C—C16C1.394 (2)
C18A—H18A0.9700C15C—H15C0.9300
C18A—H18B0.9700C18C—C19C1.504 (3)
C19A—H19A0.9600C18C—H18E0.9700
C19A—H19B0.9600C18C—H18F0.9700
C19A—H19C0.9600C19C—H19G0.9600
O1E—C18E1.460 (15)C19C—H19H0.9600
C18E—C19E1.474 (17)C19C—H19I0.9600
C18E—H18I0.9700C20C—H20G0.9600
C18E—H18J0.9700C20C—H20H0.9600
C19E—H19M0.9600C20C—H20I0.9600
C19E—H19N0.9600S1D—C10D1.6777 (16)
C19E—H19O0.9600O1D—C17D1.339 (2)
C20A—H20A0.9600O1D—C18D1.454 (2)
C20A—H20B0.9600O2D—C17D1.207 (2)
C20A—H20C0.9600F2D—C14D1.3575 (19)
S1B—C10B1.6834 (16)F1D—C12D1.3639 (19)
O1B—C17B1.3350 (19)N1D—C10D1.3824 (19)
O1B—C18B1.4639 (19)N1D—C7D1.419 (2)
O2B—C17B1.2123 (19)N1D—C6D1.451 (2)
F2B—C14B1.357 (2)N2D—C10D1.332 (2)
N1B—C10B1.384 (2)N2D—C9D1.462 (2)
N1B—C7B1.4237 (19)N2D—H1ND0.87 (2)
N1B—C6B1.4481 (19)C1D—C6D1.377 (2)
N2B—C10B1.329 (2)C1D—C2D1.395 (3)
N2B—C9B1.467 (2)C1D—H1DA0.9300
N2B—H1NB0.87 (2)C2D—C3D1.373 (3)
C1B—C6B1.382 (2)C2D—H2DA0.9300
C1B—C2B1.389 (2)C3D—C4D1.377 (3)
C1B—H1BA0.9300C3D—H3DA0.9300
C2B—C3B1.391 (3)C4D—C5D1.392 (3)
C2B—H2BA0.9300C4D—H4DA0.9300
C3B—C4B1.381 (3)C5D—C6D1.375 (3)
C3B—H3BA0.9300C5D—H5DA0.9300
C4B—C5B1.384 (2)C7D—C8D1.349 (2)
C4B—H4BA0.9300C7D—C20D1.502 (2)
C5B—C6B1.384 (2)C8D—C17D1.482 (2)
C5B—H5BA0.9300C8D—C9D1.509 (2)
C7B—C8B1.349 (2)C9D—C11D1.523 (2)
C7B—C20B1.508 (2)C9D—H9DA0.9800
C8B—C17B1.482 (2)C11D—C12D1.388 (2)
C8B—C9B1.511 (2)C11D—C16D1.394 (2)
C9B—C11B1.519 (2)C12D—C13D1.376 (2)
C9B—H9BA0.9800C13D—C14D1.380 (3)
C11B—C12B1.383 (3)C13D—H13D0.9300
C11B—C16B1.389 (2)C14D—C15D1.374 (3)
C12B—F1B1.311 (3)C15D—C16D1.393 (2)
C12B—C13B1.385 (3)C15D—H15D0.9300
C12B—H12B0.9300C16C—H16A0.9300
C13B—C14B1.372 (3)C18D—C19D1.497 (3)
C13B—H13B0.9300C18D—H18G0.9700
C14B—C15B1.362 (3)C18D—H18H0.9700
C15B—C16B1.387 (3)C19D—H19J0.9600
C15B—H15B0.9300C19D—H19K0.9600
C16B—F3B1.296 (3)C19D—H19L0.9600
C16B—H16D0.9300C20D—H20J0.9600
C18B—C19B1.500 (2)C20D—H20K0.9600
C18B—H18C0.9700C20D—H20L0.9600
C18B—H18D0.9700C16D—H16B0.9300
C10A—N1A—C7A122.11 (13)H19D—C19B—H19F109.5
C10A—N1A—C6A119.68 (13)H19E—C19B—H19F109.5
C7A—N1A—C6A118.18 (12)C7B—C20B—H20D109.5
C10A—N2A—C9A126.17 (14)C7B—C20B—H20E109.5
C10A—N2A—H1NA115.5 (15)H20D—C20B—H20E109.5
C9A—N2A—H1NA117.8 (15)C7B—C20B—H20F109.5
C6A—C1A—C2A119.57 (18)H20D—C20B—H20F109.5
C6A—C1A—H1AA120.2H20E—C20B—H20F109.5
C2A—C1A—H1AA120.2C17C—O1C—C18C116.06 (15)
C3A—C2A—C1A120.26 (17)C10C—N1C—C7C121.77 (13)
C3A—C2A—H2AA119.9C10C—N1C—C6C119.11 (13)
C1A—C2A—H2AA119.9C7C—N1C—C6C118.98 (13)
C2A—C3A—C4A119.99 (17)C10C—N2C—C9C126.50 (14)
C2A—C3A—H3AA120.0C10C—N2C—H1NC117.6 (13)
C4A—C3A—H3AA120.0C9C—N2C—H1NC113.5 (13)
C3A—C4A—C5A120.04 (18)C6C—C1C—C2C119.1 (2)
C3A—C4A—H4AA120.0C6C—C1C—H1CA120.4
C5A—C4A—H4AA120.0C2C—C1C—H1CA120.4
C6A—C5A—C4A119.42 (16)C3C—C2C—C1C120.9 (2)
C6A—C5A—H5AA120.3C3C—C2C—H2CA119.5
C4A—C5A—H5AA120.3C1C—C2C—H2CA119.5
C1A—C6A—C5A120.71 (15)C2C—C3C—C4C119.6 (2)
C1A—C6A—N1A119.92 (15)C2C—C3C—H3CA120.2
C5A—C6A—N1A119.00 (14)C4C—C3C—H3CA120.2
C8A—C7A—N1A119.05 (14)C3C—C4C—C5C120.6 (3)
C8A—C7A—C20A125.95 (14)C3C—C4C—H4CA119.7
N1A—C7A—C20A115.00 (13)C5C—C4C—H4CA119.7
C7A—C8A—C17A127.13 (14)C6C—C5C—C4C119.1 (2)
C7A—C8A—C9A121.28 (14)C6C—C5C—H5CA120.4
C17A—C8A—C9A111.50 (13)C4C—C5C—H5CA120.4
N2A—C9A—C8A109.21 (13)C5C—C6C—C1C120.58 (18)
N2A—C9A—C11A111.38 (13)C5C—C6C—N1C118.54 (18)
C8A—C9A—C11A112.98 (14)C1C—C6C—N1C120.80 (16)
N2A—C9A—H9AA107.7C8C—C7C—N1C119.93 (14)
C8A—C9A—H9AA107.7C8C—C7C—C20C125.62 (15)
C11A—C9A—H9AA107.7N1C—C7C—C20C114.36 (14)
N2A—C10A—N1A116.49 (14)C7C—C8C—C17C125.96 (14)
N2A—C10A—S1A121.62 (12)C7C—C8C—C9C121.75 (14)
N1A—C10A—S1A121.87 (12)C17C—C8C—C9C112.28 (14)
C12A—C11A—C16A116.12 (16)N2C—C9C—C8C109.13 (13)
C12A—C11A—C9A122.20 (14)N2C—C9C—C11C111.92 (12)
C16A—C11A—C9A121.68 (16)C8C—C9C—C11C113.61 (13)
F1A—C12A—C13A117.73 (19)N2C—C9C—H9CA107.3
F1A—C12A—C11A117.79 (19)C8C—C9C—H9CA107.3
C13A—C12A—C11A123.27 (16)C11C—C9C—H9CA107.3
C13A—C12A—H12A118.4N2C—C10C—N1C116.46 (14)
C11A—C12A—H12A118.4N2C—C10C—S1C121.64 (12)
C14A—C13A—C12A117.16 (18)N1C—C10C—S1C121.79 (12)
C14A—C13A—H13A121.4C12C—C11C—C16C116.66 (15)
C12A—C13A—H13A121.4C12C—C11C—C9C122.63 (14)
F2A—C14A—C15A118.70 (16)C16C—C11C—C9C120.71 (15)
F2A—C14A—C13A118.34 (18)F1C—C12C—C13C117.59 (15)
C15A—C14A—C13A122.95 (17)F1C—C12C—C11C118.72 (14)
C14A—C15A—C16A117.85 (16)C13C—C12C—C11C123.68 (16)
C14A—C15A—H15A121.1C14C—C13C—C12C116.63 (16)
C16A—C15A—H15A121.1C14C—C13C—H13C121.7
F3A—C16A—C15A117.58 (17)C12C—C13C—H13C121.7
F3A—C16A—C11A119.60 (18)F2C—C14C—C15C119.22 (16)
C15A—C16A—C11A122.65 (18)F2C—C14C—C13C117.68 (16)
C15A—C16A—H16C118.7C15C—C14C—C13C123.10 (16)
C11A—C16A—H16C118.7C14C—C15C—C16C117.98 (16)
O2A—C17A—O1A122.39 (15)C14C—C15C—H15C121.0
O2A—C17A—C8A121.07 (15)C16C—C15C—H15C121.0
O1A—C17A—C8A116.46 (14)O2C—C17C—O1C123.25 (16)
O2A—C17A—O1E126.1 (5)O2C—C17C—C8C122.56 (16)
C8A—C17A—O1E105.1 (5)O1C—C17C—C8C114.09 (15)
C17A—O1A—C18A115.92 (14)O1C—C18C—C19C106.16 (17)
O1A—C18A—C19A106.50 (15)O1C—C18C—H18E110.5
O1A—C18A—H18A110.4C19C—C18C—H18E110.5
C19A—C18A—H18A110.4O1C—C18C—H18F110.5
O1A—C18A—H18B110.4C19C—C18C—H18F110.5
C19A—C18A—H18B110.4H18E—C18C—H18F108.7
H18A—C18A—H18B108.6C18C—C19C—H19G109.5
C18E—O1E—C17A113.7 (13)C18C—C19C—H19H109.5
C19E—C18E—O1E108.7 (14)H19G—C19C—H19H109.5
C19E—C18E—H18I110.0C18C—C19C—H19I109.5
O1E—C18E—H18I110.0H19G—C19C—H19I109.5
C19E—C18E—H18J110.0H19H—C19C—H19I109.5
O1E—C18E—H18J110.0C7C—C20C—H20G109.5
H18I—C18E—H18J108.3C7C—C20C—H20H109.5
C18E—C19E—H19M109.5H20G—C20C—H20H109.5
C18E—C19E—H19N109.5C7C—C20C—H20I109.5
H19M—C19E—H19N109.5H20G—C20C—H20I109.5
C18E—C19E—H19O109.5H20H—C20C—H20I109.5
H19M—C19E—H19O109.5C17D—O1D—C18D116.44 (15)
H19N—C19E—H19O109.5C10D—N1D—C7D122.12 (13)
C7A—C20A—H20A109.5C10D—N1D—C6D117.90 (13)
C7A—C20A—H20B109.5C7D—N1D—C6D119.59 (13)
H20A—C20A—H20B109.5C10D—N2D—C9D126.23 (14)
C7A—C20A—H20C109.5C10D—N2D—H1ND119.4 (13)
H20A—C20A—H20C109.5C9D—N2D—H1ND111.7 (13)
H20B—C20A—H20C109.5C6D—C1D—C2D119.13 (19)
C17B—O1B—C18B115.51 (13)C6D—C1D—H1DA120.4
C10B—N1B—C7B122.06 (13)C2D—C1D—H1DA120.4
C10B—N1B—C6B118.97 (13)C3D—C2D—C1D120.47 (19)
C7B—N1B—C6B118.95 (13)C3D—C2D—H2DA119.8
C10B—N2B—C9B126.02 (14)C1D—C2D—H2DA119.8
C10B—N2B—H1NB117.6 (13)C2D—C3D—C4D119.87 (19)
C9B—N2B—H1NB115.0 (13)C2D—C3D—H3DA120.1
C6B—C1B—C2B119.55 (15)C4D—C3D—H3DA120.1
C6B—C1B—H1BA120.2C3D—C4D—C5D120.2 (2)
C2B—C1B—H1BA120.2C3D—C4D—H4DA119.9
C1B—C2B—C3B119.92 (17)C5D—C4D—H4DA119.9
C1B—C2B—H2BA120.0C6D—C5D—C4D119.50 (19)
C3B—C2B—H2BA120.0C6D—C5D—H5DA120.3
C4B—C3B—C2B119.86 (16)C4D—C5D—H5DA120.3
C4B—C3B—H3BA120.1C5D—C6D—C1D120.83 (17)
C2B—C3B—H3BA120.1C5D—C6D—N1D117.91 (15)
C3B—C4B—C5B120.47 (16)C1D—C6D—N1D121.24 (16)
C3B—C4B—H4BA119.8C8D—C7D—N1D119.46 (14)
C5B—C4B—H4BA119.8C8D—C7D—C20D126.84 (15)
C6B—C5B—C4B119.44 (16)N1D—C7D—C20D113.58 (14)
C6B—C5B—H5BA120.3C7D—C8D—C17D126.09 (15)
C4B—C5B—H5BA120.3C7D—C8D—C9D121.85 (14)
C1B—C6B—C5B120.76 (15)C17D—C8D—C9D112.04 (14)
C1B—C6B—N1B119.10 (14)N2D—C9D—C8D109.30 (13)
C5B—C6B—N1B119.97 (15)N2D—C9D—C11D112.04 (12)
C8B—C7B—N1B119.36 (14)C8D—C9D—C11D113.85 (13)
C8B—C7B—C20B125.95 (14)N2D—C9D—H9DA107.1
N1B—C7B—C20B114.69 (13)C8D—C9D—H9DA107.1
C7B—C8B—C17B127.42 (15)C11D—C9D—H9DA107.1
C7B—C8B—C9B121.09 (14)N2D—C10D—N1D116.46 (14)
C17B—C8B—C9B111.44 (13)N2D—C10D—S1D122.06 (12)
N2B—C9B—C8B109.39 (13)N1D—C10D—S1D121.34 (12)
N2B—C9B—C11B110.81 (13)C12D—C11D—C16D116.66 (15)
C8B—C9B—C11B113.25 (14)C12D—C11D—C9D122.91 (14)
N2B—C9B—H9BA107.7C16D—C11D—C9D120.42 (14)
C8B—C9B—H9BA107.7F1D—C12D—C13D117.75 (15)
C11B—C9B—H9BA107.7F1D—C12D—C11D118.55 (14)
N2B—C10B—N1B116.59 (14)C13D—C12D—C11D123.69 (16)
N2B—C10B—S1B121.74 (12)C12D—C13D—C14D116.90 (17)
N1B—C10B—S1B121.64 (12)C12D—C13D—H13D121.6
C12B—C11B—C16B116.02 (17)C14D—C13D—H13D121.6
C12B—C11B—C9B122.21 (15)F2D—C14D—C15D119.14 (16)
C16B—C11B—C9B121.76 (16)F2D—C14D—C13D117.89 (17)
F1B—C12B—C11B116.75 (19)C15D—C14D—C13D122.97 (16)
F1B—C12B—C13B118.0 (2)C14D—C15D—C16D117.94 (16)
C11B—C12B—C13B123.32 (18)C14D—C15D—H15D121.0
C11B—C12B—H12B118.3C16D—C15D—H15D121.0
C13B—C12B—H12B118.3C11C—C16C—C15C121.89 (16)
C14B—C13B—C12B117.3 (2)C11C—C16C—H16A119.1
C14B—C13B—H13B121.3C15C—C16C—H16A119.1
C12B—C13B—H13B121.3O2D—C17D—O1D123.09 (16)
F2B—C14B—C15B118.68 (18)O2D—C17D—C8D122.62 (16)
F2B—C14B—C13B118.6 (2)O1D—C17D—C8D114.16 (15)
C15B—C14B—C13B122.72 (18)O1D—C18D—C19D105.99 (18)
C14B—C15B—C16B117.95 (18)O1D—C18D—H18G110.5
C14B—C15B—H15B121.0C19D—C18D—H18G110.5
C16B—C15B—H15B121.0O1D—C18D—H18H110.5
F3B—C16B—C15B117.85 (18)C19D—C18D—H18H110.5
F3B—C16B—C11B119.27 (19)H18G—C18D—H18H108.7
C15B—C16B—C11B122.7 (2)C18D—C19D—H19J109.5
C15B—C16B—H16D118.7C18D—C19D—H19K109.5
C11B—C16B—H16D118.7H19J—C19D—H19K109.5
O2B—C17B—O1B122.80 (15)C18D—C19D—H19L109.5
O2B—C17B—C8B120.63 (15)H19J—C19D—H19L109.5
O1B—C17B—C8B116.57 (14)H19K—C19D—H19L109.5
O1B—C18B—C19B107.26 (14)C7D—C20D—H20J109.5
O1B—C18B—H18C110.3C7D—C20D—H20K109.5
C19B—C18B—H18C110.3H20J—C20D—H20K109.5
O1B—C18B—H18D110.3C7D—C20D—H20L109.5
C19B—C18B—H18D110.3H20J—C20D—H20L109.5
H18C—C18B—H18D108.5H20K—C20D—H20L109.5
C18B—C19B—H19D109.5C15D—C16D—C11D121.80 (16)
C18B—C19B—H19E109.5C15D—C16D—H16B119.1
H19D—C19B—H19E109.5C11D—C16D—H16B119.1
C18B—C19B—H19F109.5
C6A—C1A—C2A—C3A0.8 (3)C18B—O1B—C17B—C8B177.07 (14)
C1A—C2A—C3A—C4A−0.2 (3)C7B—C8B—C17B—O2B170.72 (17)
C2A—C3A—C4A—C5A0.0 (3)C9B—C8B—C17B—O2B−6.5 (2)
C3A—C4A—C5A—C6A−0.4 (3)C7B—C8B—C17B—O1B−9.4 (3)
C2A—C1A—C6A—C5A−1.2 (3)C9B—C8B—C17B—O1B173.40 (14)
C2A—C1A—C6A—N1A171.70 (16)C17B—O1B—C18B—C19B178.89 (15)
C4A—C5A—C6A—C1A1.0 (2)C6C—C1C—C2C—C3C−2.2 (3)
C4A—C5A—C6A—N1A−171.93 (15)C1C—C2C—C3C—C4C1.0 (3)
C10A—N1A—C6A—C1A87.56 (19)C2C—C3C—C4C—C5C1.2 (4)
C7A—N1A—C6A—C1A−90.26 (19)C3C—C4C—C5C—C6C−2.2 (4)
C10A—N1A—C6A—C5A−99.42 (18)C4C—C5C—C6C—C1C1.0 (3)
C7A—N1A—C6A—C5A82.75 (19)C4C—C5C—C6C—N1C−175.91 (19)
C10A—N1A—C7A—C8A14.0 (2)C2C—C1C—C6C—C5C1.1 (3)
C6A—N1A—C7A—C8A−168.28 (15)C2C—C1C—C6C—N1C177.95 (15)
C10A—N1A—C7A—C20A−165.36 (15)C10C—N1C—C6C—C5C−107.12 (19)
C6A—N1A—C7A—C20A12.4 (2)C7C—N1C—C6C—C5C68.7 (2)
N1A—C7A—C8A—C17A178.96 (15)C10C—N1C—C6C—C1C76.0 (2)
C20A—C7A—C8A—C17A−1.8 (3)C7C—N1C—C6C—C1C−108.22 (18)
N1A—C7A—C8A—C9A2.6 (2)C10C—N1C—C7C—C8C9.8 (2)
C20A—C7A—C8A—C9A−178.18 (16)C6C—N1C—C7C—C8C−165.86 (15)
C10A—N2A—C9A—C8A26.3 (2)C10C—N1C—C7C—C20C−166.89 (15)
C10A—N2A—C9A—C11A−99.17 (18)C6C—N1C—C7C—C20C17.4 (2)
C7A—C8A—C9A—N2A−20.1 (2)N1C—C7C—C8C—C17C178.20 (15)
C17A—C8A—C9A—N2A163.02 (14)C20C—C7C—C8C—C17C−5.5 (3)
C7A—C8A—C9A—C11A104.46 (18)N1C—C7C—C8C—C9C−3.3 (2)
C17A—C8A—C9A—C11A−72.43 (17)C20C—C7C—C8C—C9C173.04 (15)
C9A—N2A—C10A—N1A−12.7 (2)C10C—N2C—C9C—C8C25.2 (2)
C9A—N2A—C10A—S1A168.72 (13)C10C—N2C—C9C—C11C−101.43 (17)
C7A—N1A—C10A—N2A−9.3 (2)C7C—C8C—C9C—N2C−12.0 (2)
C6A—N1A—C10A—N2A172.99 (14)C17C—C8C—C9C—N2C166.75 (13)
C7A—N1A—C10A—S1A169.28 (12)C7C—C8C—C9C—C11C113.68 (17)
C6A—N1A—C10A—S1A−8.5 (2)C17C—C8C—C9C—C11C−67.59 (18)
N2A—C9A—C11A—C12A73.41 (19)C9C—N2C—C10C—N1C−20.7 (2)
C8A—C9A—C11A—C12A−49.9 (2)C9C—N2C—C10C—S1C163.05 (12)
N2A—C9A—C11A—C16A−106.84 (17)C7C—N1C—C10C—N2C1.4 (2)
C8A—C9A—C11A—C16A129.81 (16)C6C—N1C—C10C—N2C177.09 (14)
C16A—C11A—C12A—F1A166.80 (19)C7C—N1C—C10C—S1C177.69 (12)
C9A—C11A—C12A—F1A−13.4 (3)C6C—N1C—C10C—S1C−6.6 (2)
C16A—C11A—C12A—C13A−0.3 (3)N2C—C9C—C11C—C12C54.2 (2)
C9A—C11A—C12A—C13A179.47 (16)C8C—C9C—C11C—C12C−70.00 (19)
F1A—C12A—C13A—C14A−166.5 (2)N2C—C9C—C11C—C16C−125.58 (16)
C11A—C12A—C13A—C14A0.6 (3)C8C—C9C—C11C—C16C110.26 (17)
C12A—C13A—C14A—F2A179.39 (16)C16C—C11C—C12C—F1C−179.65 (14)
C12A—C13A—C14A—C15A−0.3 (3)C9C—C11C—C12C—F1C0.6 (2)
F2A—C14A—C15A—C16A−179.91 (15)C16C—C11C—C12C—C13C0.6 (2)
C13A—C14A—C15A—C16A−0.2 (3)C9C—C11C—C12C—C13C−179.18 (15)
C14A—C15A—C16A—F3A175.75 (17)F1C—C12C—C13C—C14C177.93 (14)
C14A—C15A—C16A—C11A0.5 (3)C11C—C12C—C13C—C14C−2.3 (3)
C12A—C11A—C16A—F3A−175.39 (17)C12C—C13C—C14C—F2C−177.77 (14)
C9A—C11A—C16A—F3A4.8 (2)C12C—C13C—C14C—C15C2.3 (3)
C12A—C11A—C16A—C15A−0.3 (2)F2C—C14C—C15C—C16C179.43 (14)
C9A—C11A—C16A—C15A179.97 (15)C13C—C14C—C15C—C16C−0.7 (3)
C7A—C8A—C17A—O2A−173.23 (17)C18C—O1C—C17C—O2C−2.7 (2)
C9A—C8A—C17A—O2A3.4 (2)C18C—O1C—C17C—C8C−179.13 (14)
C7A—C8A—C17A—O1A3.7 (3)C7C—C8C—C17C—O2C158.63 (17)
C9A—C8A—C17A—O1A−179.66 (16)C9C—C8C—C17C—O2C−20.0 (2)
C7A—C8A—C17A—O1E35.7 (7)C7C—C8C—C17C—O1C−24.9 (2)
C9A—C8A—C17A—O1E−147.7 (7)C9C—C8C—C17C—O1C156.40 (14)
O2A—C17A—O1A—C18A0.4 (3)C17C—O1C—C18C—C19C−168.78 (15)
C8A—C17A—O1A—C18A−176.45 (16)C6D—C1D—C2D—C3D−0.4 (3)
O1E—C17A—O1A—C18A108.0 (9)C1D—C2D—C3D—C4D−1.7 (3)
C17A—O1A—C18A—C19A−176.8 (2)C2D—C3D—C4D—C5D2.6 (3)
O2A—C17A—O1E—C18E34.5 (16)C3D—C4D—C5D—C6D−1.4 (3)
O1A—C17A—O1E—C18E−60.2 (12)C4D—C5D—C6D—C1D−0.7 (3)
C8A—C17A—O1E—C18E−176.3 (11)C4D—C5D—C6D—N1D−179.23 (16)
C17A—O1E—C18E—C19E85 (2)C2D—C1D—C6D—C5D1.5 (3)
C6B—C1B—C2B—C3B−0.1 (2)C2D—C1D—C6D—N1D−179.93 (15)
C1B—C2B—C3B—C4B0.0 (3)C10D—N1D—C6D—C5D90.06 (19)
C2B—C3B—C4B—C5B0.3 (3)C7D—N1D—C6D—C5D−82.95 (19)
C3B—C4B—C5B—C6B−0.5 (3)C10D—N1D—C6D—C1D−88.51 (19)
C2B—C1B—C6B—C5B−0.1 (2)C7D—N1D—C6D—C1D98.48 (19)
C2B—C1B—C6B—N1B175.12 (14)C10D—N1D—C7D—C8D−9.7 (2)
C4B—C5B—C6B—C1B0.4 (2)C6D—N1D—C7D—C8D162.99 (15)
C4B—C5B—C6B—N1B−174.76 (15)C10D—N1D—C7D—C20D166.60 (15)
C10B—N1B—C6B—C1B92.31 (18)C6D—N1D—C7D—C20D−20.7 (2)
C7B—N1B—C6B—C1B−88.92 (18)N1D—C7D—C8D—C17D179.80 (15)
C10B—N1B—C6B—C5B−92.45 (18)C20D—C7D—C8D—C17D4.0 (3)
C7B—N1B—C6B—C5B86.31 (19)N1D—C7D—C8D—C9D1.9 (2)
C10B—N1B—C7B—C8B−12.3 (2)C20D—C7D—C8D—C9D−173.87 (16)
C6B—N1B—C7B—C8B168.95 (15)C10D—N2D—C9D—C8D−25.7 (2)
C10B—N1B—C7B—C20B167.73 (15)C10D—N2D—C9D—C11D101.43 (18)
C6B—N1B—C7B—C20B−11.0 (2)C7D—C8D—C9D—N2D13.5 (2)
N1B—C7B—C8B—C17B−179.67 (15)C17D—C8D—C9D—N2D−164.67 (13)
C20B—C7B—C8B—C17B0.3 (3)C7D—C8D—C9D—C11D−112.62 (18)
N1B—C7B—C8B—C9B−2.7 (2)C17D—C8D—C9D—C11D69.20 (18)
C20B—C7B—C8B—C9B177.27 (15)C9D—N2D—C10D—N1D20.1 (2)
C10B—N2B—C9B—C8B−26.8 (2)C9D—N2D—C10D—S1D−164.18 (12)
C10B—N2B—C9B—C11B98.75 (19)C7D—N1D—C10D—N2D−0.6 (2)
C7B—C8B—C9B—N2B19.7 (2)C6D—N1D—C10D—N2D−173.40 (14)
C17B—C8B—C9B—N2B−162.91 (13)C7D—N1D—C10D—S1D−176.36 (12)
C7B—C8B—C9B—C11B−104.48 (18)C6D—N1D—C10D—S1D10.8 (2)
C17B—C8B—C9B—C11B72.96 (17)N2D—C9D—C11D—C12D−53.4 (2)
C9B—N2B—C10B—N1B14.6 (2)C8D—C9D—C11D—C12D71.2 (2)
C9B—N2B—C10B—S1B−167.28 (13)N2D—C9D—C11D—C16D125.69 (15)
C7B—N1B—C10B—N2B6.8 (2)C8D—C9D—C11D—C16D−109.64 (17)
C6B—N1B—C10B—N2B−174.44 (14)C16D—C11D—C12D—F1D179.49 (14)
C7B—N1B—C10B—S1B−171.33 (12)C9D—C11D—C12D—F1D−1.4 (2)
C6B—N1B—C10B—S1B7.4 (2)C16D—C11D—C12D—C13D−1.5 (2)
N2B—C9B—C11B—C12B−74.1 (2)C9D—C11D—C12D—C13D177.69 (15)
C8B—C9B—C11B—C12B49.3 (2)F1D—C12D—C13D—C14D−178.42 (15)
N2B—C9B—C11B—C16B105.33 (17)C11D—C12D—C13D—C14D2.5 (3)
C8B—C9B—C11B—C16B−131.32 (16)C12D—C13D—C14D—F2D177.85 (15)
C16B—C11B—C12B—F1B−163.7 (2)C12D—C13D—C14D—C15D−1.8 (3)
C9B—C11B—C12B—F1B15.8 (3)F2D—C14D—C15D—C16D−179.53 (15)
C16B—C11B—C12B—C13B0.4 (3)C13D—C14D—C15D—C16D0.1 (3)
C9B—C11B—C12B—C13B179.81 (17)C12C—C11C—C16C—C15C1.2 (2)
F1B—C12B—C13B—C14B163.0 (2)C9C—C11C—C16C—C15C−179.01 (14)
C11B—C12B—C13B—C14B−0.8 (3)C14C—C15C—C16C—C11C−1.2 (2)
C12B—C13B—C14B—F2B−178.93 (17)C18D—O1D—C17D—O2D4.0 (2)
C12B—C13B—C14B—C15B0.6 (3)C18D—O1D—C17D—C8D−179.82 (14)
F2B—C14B—C15B—C16B179.56 (16)C7D—C8D—C17D—O2D−157.11 (18)
C13B—C14B—C15B—C16B0.0 (3)C9D—C8D—C17D—O2D21.0 (2)
C14B—C15B—C16B—F3B−175.16 (18)C7D—C8D—C17D—O1D26.7 (2)
C14B—C15B—C16B—C11B−0.5 (3)C9D—C8D—C17D—O1D−155.20 (14)
C12B—C11B—C16B—F3B174.88 (18)C17D—O1D—C18D—C19D167.69 (16)
C9B—C11B—C16B—F3B−4.6 (3)C14D—C15D—C16D—C11D1.0 (2)
C12B—C11B—C16B—C15B0.3 (3)C12D—C11D—C16D—C15D−0.4 (2)
C9B—C11B—C16B—C15B−179.13 (16)C9D—C11D—C16D—C15D−179.55 (15)
C18B—O1B—C17B—O2B−3.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2A—H1NA···S1B0.86 (2)2.63 (2)3.4521 (15)161.1 (19)
N2B—H1NB···S1A0.87 (2)2.624 (19)3.4632 (15)163.1 (18)
N2C—H1NC···S1Ci0.90 (2)2.41 (2)3.2686 (15)160.0 (17)
N2D—H1ND···S1Dii0.87 (2)2.42 (2)3.2537 (15)159.7 (17)
C9B—H9BA···O2Ciii0.982.503.199 (2)128
C16C—H16A···O2Ai0.932.463.143 (2)130
C16D—H16B···O2Biv0.932.473.146 (2)130
C18A—H18B···O2Bv0.972.523.446 (3)159
C18B—H18C···O2Avi0.972.503.427 (2)160

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2538).

References

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