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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o810–o811.
Published online 2008 April 10. doi:  10.1107/S1600536808009306
PMCID: PMC2961240

N-(3-Oxo-1-thia-4-aza­spiro­[4.5]dec-4-yl)-6-phenyl­imidazo[2,1-b][1,3]thia­zole-3-acetamide hemihydrate

Abstract

The title compound, C21H22N4O2S2·0.5H2O, crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the phenyl and imidazothiazole ring systems are 19.16 (9) and 21.37 (9)°. In the imidazothiazole ring systems, the cyclohexane rings adopt chair conformations, while the thiazole rings have distorted envelope conformations. The two mol­ecules are stabilized by intra­molecular N—H(...)O, O—H(...)O and C—H(...)S inter­actions and the crystal structure is stabilized by inter­molecular N—H(...)O, O—H(...)O, C—H(...)O and C—H(...)N inter­actions.

Related literature

For related literature, see: Akkurt et al. (2005 [triangle], 2007 [triangle]); Allen et al. (1987 [triangle]); Amarouch et al. (1988 [triangle]); Andreani et al. (1998 [triangle]); Cremer & Pople (1975 [triangle]); Devlin & Hargrave (1989 [triangle]); Gürsoy & Ulusoy Güzeldemirci (2007 [triangle]); Srimanth et al. (2002 [triangle]); Ulusoy (2002 [triangle]); Ur et al. (2004 [triangle]); Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Büyükgüngör (2005 [triangle]); Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Heinemann (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o810-scheme1.jpg

Experimental

Crystal data

  • C21H22N4O2S2·0.5H2O
  • M r = 435.58
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o810-efi1.jpg
  • a = 11.0175 (3) Å
  • b = 11.8817 (3) Å
  • c = 17.6162 (5) Å
  • α = 75.123 (2)°
  • β = 73.502 (2)°
  • γ = 81.012 (2)°
  • V = 2128.36 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 296 K
  • 0.52 × 0.39 × 0.25 mm

Data collection

  • Stoe IPDSII diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.869, T max = 0.934
  • 38012 measured reflections
  • 8351 independent reflections
  • 6705 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.098
  • S = 1.02
  • 8351 reflections
  • 538 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009306/hg2390sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009306/hg2390Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

Imidazo[2,1-b]thiazolederivatives have demonstrated a broad range of biological activities, including immunoregulatory (Devlin & Hargrave, 1989), anticancer (Srimanth et al., 2002), antihelmintic (Amarouch et al., 1988), cardiotonic (Andreani et al., 1998) and antimycobacterial (Ur et al., 2004). In connection with our previous papers on the synthesis of imidazo[2,1-b]thiazoles (Gürsoy & Ulusoy Güzeldemirci, 2007) and their crystal structures (Akkurt et al., 2007), we report here the crystal structure of the title spiro derivative, 6-phenyl-N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-imidazo[2,1-\ b]thiazole-3-acetamide hemihydrate (III) (Scheme 1 and 2).

In the two molecules A (Fig. 1) and B (Fig. 2) of the title compound, the bond lengths in two molecules are normal (Allen et al., 1987). The mean C—S bond length [1.778 (2) Å] in two molecules may be compared with the corresponding values in similar molecules [1.737 (5) Å (Akkurt et al., 2007), 1.7588 (2) Å (Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Büyükgüngör, 2005), 1.783 (2) Å (Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Heinemann, 2005) and 1.729 (2) Å (Akkurt et al., 2005)].

The thiazole and imidazole rings in the two molecules A [with S1] and B [with S3] of the title compound are essentially coplanar, with a dihedral angle of 2.29 (10) and 1.33 (10)°, respectively. The dihedral angles of the benzene rings and the mean plane of the thiazole and imidazole rings systems are19.16 (9) and 21.37 (9)° for molecules A and B, respectively. The other thiazole rings have distorted envelope conformations [puckering parameters (Cremer & Pople, 1975): Q(2) = 0.1773 (2) Å, [var phi](2) = 342.0 (6) ° for molecule A, and Q(2) = 0.193 (2) Å, [var phi](2) = 170.2 (5) ° for molecule B], while the cyclohexane rings to connected to them have chair conformation for two molecules in the asymmetric unit [puckering parameters: QT = 0.567 (3) Å, θ =178.1 (3) °, [var phi] = 179 (7) ° for molecule A, and QT = 0.570 (2) Å, θ =179.6 (2) °, [var phi] = 109 (6) ° for molecule B].

The two molecules are stabilized by intramolecular N—H···O, O—H···O and C—H···S interactions and the crystal packing is stabilized by intermolecular N—H···O, O—H···O, C—H···O and C—H..N hydrogen bonding interactions (Table 1, Fig. 3).

Experimental

A mixture of 6-phenyl-N-(cyclohexylidene)imidazo[2,1-b]thiazole-3-\ acetohydrazide (0.005 mol) and HSCH2COOH (0.01 mol) was refluxed in dry benzene (30 ml) using a Dean-Stark trap for 48 h. Excess benzene was evaporated in vacuo.The residue was triturated with saturated NaHCO3 until CO2 evolution ceased and then allowed to stand overnight. The solid thus obtained was filtered, washed with H2O and recrystallized from C2H5OH to yield colourless prisms of (III) (Ulusoy, 2002).

IR [ν, cm-1,KBr]: 3390, 3272 (O—H, N—H), 1718,1670 (C=O). 1H-NMR [δ, p.p.m.,DMSO-d6]: 0.92–1.78 (10H, m, cyclohex.), 3.60 (2H, s, thiazolidinone SCH2),3.93 (2H, s, CH2CO), 7.10(1H, s, imidazothiazole C2—H),7.21–7.43 (3H, m, ph.), 7.81 (2H, d, J= 7.6 Hz, ph.), 8.23 (1H, s, imidazothiazole C5—H),10.45 (1H, s, CONH). 13C-NMR(APT) [δ, p.p.m., DMSO-d6]: 22.64 (cyclohex. C4), 23.70 (cyclohex. C3 and C5),27.62 (thiazolidinone C5), 32.48 (s, CH2CO), 36.69 (cyclohex. C2 and C6),71.91 (thiazolidinone C2), 108.15 (imidazothiazole C5),110.12 (imidazothiazole C2), 124.36 (ph. C4), 126.77 (ph.C3 and C5), 128.40 (ph. C2 and C6),125.68, 134.08, 145.90, 148.42 (imidazothiazole C3, C6, C7aand ph. C1), 166.54 (CONH), 167.64 (thiazolidinone C=O). EI—MS (70 eV), m/z (%): 426 (M+, 70), 353 (72), 257 (9), 241 (69), 214 (100). Analysis calculated for C21H22N4O2S2.0.5H2O: C 57.90, H 5.32, N 12.86%. Found: C 57.87, H 5.77, N 12.94%.

Refinement

The H atoms of the water molecule were found from a difference Fourier map and refined freely. DFIX restraints were applied to the O—H distances [0.83 (2) Å] and H—O—H angles [by restraining the H···H distances to 1.40 (2) Å]. The other H atoms were positioned geometrically, with N—H = 0.86 Å, C—H = 0.93 and 0.97 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
An ORTEP-3 plot of the molecule A in the asymmetric unit, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
Fig. 2.
An ORTEP-3 plot of the molecule Bs in the asymmetric unit, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
Fig. 3.
View of the packing and hydrogen bonding interactions for the title compound in the unitcell.
Fig. 4.
The formation of the title compound.

Crystal data

C21H22N4O2S2·0.5H2OZ = 4
Mr = 435.58F000 = 916
Triclinic, P1Dx = 1.359 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 11.0175 (3) ÅCell parameters from 51089 reflections
b = 11.8817 (3) Åθ = 1.8–28.0º
c = 17.6162 (5) ŵ = 0.28 mm1
α = 75.123 (2)ºT = 296 K
β = 73.502 (2)ºBlock, colourless
γ = 81.012 (2)º0.52 × 0.39 × 0.25 mm
V = 2128.36 (10) Å3

Data collection

Stoe IPDS2 diffractometer8351 independent reflections
Monochromator: plane graphite6705 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.054
T = 296 Kθmax = 26.0º
ω scansθmin = 1.8º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)h = −13→13
Tmin = 0.869, Tmax = 0.934k = −14→14
38012 measured reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098  w = 1/[σ2(Fo2) + (0.0455P)2 + 0.3604P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
8351 reflectionsΔρmax = 0.29 e Å3
538 parametersΔρmin = −0.34 e Å3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.05906 (5)−0.07649 (4)0.91226 (4)0.0650 (2)
S20.82255 (5)0.06276 (5)0.64335 (3)0.0633 (2)
O10.51521 (13)−0.09814 (10)0.86877 (9)0.0613 (4)
O20.77147 (14)−0.03089 (17)0.87525 (9)0.0824 (6)
N10.21182 (12)0.08291 (11)0.86246 (8)0.0406 (4)
N20.07989 (15)0.12137 (13)0.78125 (9)0.0525 (5)
N30.55426 (12)0.08920 (12)0.84165 (8)0.0423 (4)
N40.66458 (12)0.07339 (12)0.78224 (8)0.0438 (4)
C10.16656 (17)0.29982 (16)0.68388 (11)0.0506 (5)
C20.1063 (2)0.2917 (2)0.62638 (12)0.0639 (7)
C30.1088 (2)0.3821 (3)0.55737 (14)0.0811 (9)
C40.1708 (3)0.4788 (2)0.54542 (14)0.0822 (9)
C50.2302 (2)0.4874 (2)0.60160 (15)0.0767 (8)
C60.2283 (2)0.39910 (17)0.67062 (13)0.0632 (7)
C70.16624 (16)0.20488 (15)0.75640 (10)0.0457 (5)
C80.24710 (16)0.18353 (14)0.80548 (10)0.0437 (5)
C90.25238 (15)0.00677 (14)0.92704 (10)0.0418 (5)
C100.17980 (17)−0.08177 (16)0.95955 (12)0.0526 (6)
C110.11095 (17)0.05086 (15)0.84477 (11)0.0476 (5)
C120.36795 (15)0.02720 (16)0.94737 (10)0.0443 (5)
C130.48551 (15)−0.00160 (14)0.88323 (10)0.0410 (5)
C140.76563 (16)0.00525 (18)0.80555 (11)0.0526 (6)
C150.86737 (18)−0.0181 (2)0.73343 (12)0.0615 (7)
C160.65776 (15)0.10149 (14)0.69704 (10)0.0415 (5)
C170.56447 (17)0.03156 (16)0.68369 (11)0.0494 (6)
C180.5583 (2)0.0620 (2)0.59546 (13)0.0697 (8)
C190.5257 (3)0.1911 (3)0.56671 (16)0.0926 (10)
C200.6163 (3)0.2626 (2)0.58065 (15)0.0890 (9)
C210.6218 (2)0.23148 (16)0.66925 (13)0.0635 (7)
S30.00085 (5)0.34118 (5)0.95204 (3)0.0644 (2)
S40.80682 (4)0.45925 (4)0.68876 (3)0.0499 (1)
O30.45903 (13)0.30931 (11)0.88067 (9)0.0627 (5)
O40.72609 (13)0.31913 (13)0.91780 (8)0.0676 (5)
N50.16872 (13)0.48752 (12)0.89897 (9)0.0461 (5)
N60.02651 (14)0.54441 (14)0.82469 (10)0.0563 (5)
N70.52947 (12)0.47506 (11)0.88527 (8)0.0395 (4)
N80.64254 (12)0.45960 (11)0.82786 (8)0.0415 (4)
C220.12270 (18)0.72081 (17)0.72858 (12)0.0572 (6)
C230.0572 (2)0.7221 (2)0.67113 (13)0.0662 (7)
C240.0637 (2)0.8126 (2)0.60334 (15)0.0811 (9)
C250.1349 (3)0.9027 (3)0.59114 (15)0.0872 (9)
C260.2000 (2)0.9046 (2)0.64714 (17)0.0863 (9)
C270.1938 (2)0.81328 (19)0.71592 (15)0.0714 (8)
C280.11981 (17)0.62186 (16)0.79871 (12)0.0518 (6)
C290.20755 (16)0.58894 (15)0.84390 (11)0.0494 (6)
C300.20970 (16)0.40507 (15)0.96034 (11)0.0459 (5)
C310.12971 (18)0.32183 (17)0.99445 (12)0.0559 (6)
C320.05979 (16)0.46679 (16)0.88438 (12)0.0508 (6)
C330.33060 (15)0.41641 (16)0.97807 (11)0.0464 (5)
C340.44507 (15)0.39476 (14)0.90929 (10)0.0416 (5)
C350.73393 (15)0.37844 (15)0.84930 (11)0.0456 (5)
C360.84643 (17)0.37065 (17)0.77895 (11)0.0537 (6)
C370.66435 (15)0.53459 (13)0.74539 (10)0.0400 (5)
C380.55215 (17)0.54151 (16)0.70950 (11)0.0498 (6)
C390.5738 (2)0.6200 (2)0.62431 (13)0.0687 (8)
C400.6054 (2)0.74073 (19)0.62337 (15)0.0780 (9)
C410.7171 (2)0.73238 (17)0.65896 (13)0.0642 (7)
C420.69282 (18)0.65648 (15)0.74490 (11)0.0500 (6)
O50.43460 (15)−0.31518 (11)0.92938 (9)0.0647 (5)
H20.064200.226200.633800.0770*
H30.067900.376400.519200.0970*
H3A0.529600.157200.852000.0510*
H40.172500.538500.499200.0990*
H50.272300.553100.593500.0920*
H60.268800.406400.708600.0760*
H80.312300.227600.801300.0520*
H100.19230−0.141101.003500.0630*
H12A0.37230−0.021501.000100.0530*
H12B0.363800.108300.950000.0530*
H15A0.87850−0.101000.734400.0740*
H15B0.947200.005400.734400.0740*
H17A0.480600.047300.718100.0590*
H17B0.59000−0.051200.699300.0590*
H18A0.639700.038500.561700.0840*
H18B0.494700.018900.589900.0840*
H19A0.439500.212500.595600.1110*
H19B0.529400.208500.509200.1110*
H20A0.588900.345100.565500.1070*
H20B0.700600.248700.546300.1070*
H21A0.683800.275700.675600.0760*
H21B0.539500.252900.703100.0760*
H70.513400.536000.905500.0470*
H230.008400.661100.678700.0790*
H240.019200.812100.565800.0970*
H250.139700.963000.545000.1050*
H260.247800.966500.639100.1040*
H270.237800.814700.753500.0860*
H290.278200.626900.838500.0590*
H310.141600.259401.036800.0670*
H33A0.338100.360701.027900.0560*
H33B0.329300.494300.986200.0560*
H36A0.868100.290100.773900.0640*
H36B0.919100.398300.787100.0640*
H38A0.475800.571800.744500.0600*
H38B0.539300.463600.707300.0600*
H39A0.643100.584200.587600.0830*
H39B0.498000.627800.605200.0830*
H40A0.625200.786500.567900.0940*
H40B0.532000.780600.654500.0940*
H41A0.732500.810200.659900.0770*
H41B0.792600.699400.624800.0770*
H42A0.621400.692400.780200.0600*
H42B0.766900.650500.765500.0600*
H5A0.459 (2)−0.2488 (15)0.9077 (12)0.0750*
H5B0.384 (2)−0.3144 (19)0.9756 (10)0.0750*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0629 (3)0.0560 (3)0.0770 (4)−0.0232 (2)−0.0327 (3)0.0105 (2)
S20.0430 (2)0.0949 (4)0.0429 (3)−0.0046 (2)0.0006 (2)−0.0132 (2)
O10.0593 (8)0.0384 (6)0.0690 (9)−0.0023 (6)0.0044 (7)−0.0063 (6)
O20.0527 (8)0.1431 (15)0.0474 (8)0.0145 (9)−0.0170 (7)−0.0237 (9)
N10.0368 (7)0.0405 (7)0.0420 (7)−0.0023 (5)−0.0119 (6)−0.0036 (6)
N20.0518 (9)0.0530 (8)0.0545 (9)−0.0033 (7)−0.0239 (7)−0.0044 (7)
N30.0376 (7)0.0424 (7)0.0424 (7)−0.0032 (6)−0.0002 (6)−0.0128 (6)
N40.0356 (7)0.0531 (8)0.0401 (7)−0.0056 (6)−0.0024 (6)−0.0130 (6)
C10.0442 (9)0.0545 (10)0.0407 (9)0.0109 (8)−0.0059 (7)−0.0035 (8)
C20.0599 (12)0.0743 (13)0.0494 (11)0.0076 (10)−0.0155 (9)−0.0060 (10)
C30.0772 (15)0.1069 (19)0.0469 (12)0.0196 (14)−0.0211 (11)−0.0067 (12)
C40.0858 (17)0.0768 (15)0.0532 (13)0.0167 (13)−0.0061 (12)0.0121 (11)
C50.0836 (16)0.0564 (12)0.0642 (14)0.0056 (11)−0.0017 (12)0.0056 (10)
C60.0681 (13)0.0525 (11)0.0566 (12)0.0034 (9)−0.0112 (10)−0.0011 (9)
C70.0420 (9)0.0455 (9)0.0447 (9)0.0026 (7)−0.0103 (7)−0.0063 (7)
C80.0401 (8)0.0418 (8)0.0443 (9)−0.0037 (7)−0.0098 (7)−0.0023 (7)
C90.0362 (8)0.0467 (9)0.0363 (8)0.0013 (7)−0.0081 (6)−0.0030 (7)
C100.0452 (9)0.0513 (10)0.0549 (11)−0.0054 (8)−0.0166 (8)0.0043 (8)
C110.0452 (9)0.0448 (9)0.0539 (10)−0.0060 (7)−0.0192 (8)−0.0048 (8)
C120.0349 (8)0.0588 (10)0.0346 (8)−0.0031 (7)−0.0070 (6)−0.0053 (7)
C130.0359 (8)0.0446 (9)0.0378 (8)−0.0011 (7)−0.0094 (6)−0.0028 (7)
C140.0363 (9)0.0787 (12)0.0448 (10)−0.0029 (8)−0.0096 (7)−0.0198 (9)
C150.0402 (9)0.0950 (15)0.0507 (11)0.0047 (9)−0.0099 (8)−0.0272 (10)
C160.0402 (8)0.0405 (8)0.0401 (9)−0.0058 (7)−0.0038 (7)−0.0087 (7)
C170.0485 (10)0.0514 (10)0.0506 (10)−0.0054 (8)−0.0127 (8)−0.0148 (8)
C180.0665 (13)0.0924 (16)0.0579 (13)−0.0055 (12)−0.0232 (10)−0.0230 (11)
C190.0980 (19)0.112 (2)0.0586 (14)0.0179 (17)−0.0357 (14)−0.0017 (14)
C200.113 (2)0.0595 (13)0.0659 (15)0.0046 (13)−0.0101 (14)0.0143 (11)
C210.0802 (14)0.0389 (9)0.0608 (12)−0.0082 (9)−0.0071 (10)−0.0029 (8)
S30.0473 (3)0.0729 (3)0.0725 (3)−0.0255 (2)−0.0150 (2)−0.0040 (3)
S40.0475 (2)0.0523 (2)0.0451 (2)0.0038 (2)−0.0066 (2)−0.0133 (2)
O30.0584 (8)0.0493 (7)0.0831 (10)−0.0109 (6)−0.0039 (7)−0.0319 (7)
O40.0530 (8)0.0756 (9)0.0524 (8)0.0118 (7)−0.0103 (6)0.0098 (7)
N50.0353 (7)0.0495 (8)0.0531 (9)−0.0066 (6)−0.0074 (6)−0.0136 (7)
N60.0440 (8)0.0646 (10)0.0600 (10)−0.0044 (7)−0.0123 (7)−0.0148 (8)
N70.0353 (7)0.0365 (7)0.0453 (8)−0.0025 (5)−0.0061 (6)−0.0120 (6)
N80.0345 (7)0.0412 (7)0.0433 (7)0.0005 (5)−0.0063 (6)−0.0060 (6)
C220.0445 (10)0.0602 (11)0.0560 (11)0.0065 (8)−0.0009 (8)−0.0137 (9)
C230.0595 (12)0.0724 (13)0.0585 (13)0.0107 (10)−0.0097 (10)−0.0160 (10)
C240.0741 (15)0.0959 (18)0.0574 (14)0.0163 (14)−0.0077 (11)−0.0139 (13)
C250.0711 (15)0.0965 (19)0.0581 (14)0.0143 (14)0.0064 (12)0.0069 (13)
C260.0650 (14)0.0745 (15)0.0913 (19)−0.0087 (12)0.0080 (14)0.0007 (13)
C270.0578 (12)0.0701 (13)0.0724 (14)−0.0005 (10)−0.0078 (10)−0.0044 (11)
C280.0431 (9)0.0535 (10)0.0553 (11)0.0015 (8)−0.0060 (8)−0.0168 (8)
C290.0397 (9)0.0477 (9)0.0575 (11)−0.0054 (7)−0.0065 (8)−0.0116 (8)
C300.0387 (8)0.0503 (9)0.0476 (10)−0.0081 (7)−0.0056 (7)−0.0128 (8)
C310.0472 (10)0.0613 (11)0.0568 (11)−0.0165 (8)−0.0096 (8)−0.0063 (9)
C320.0371 (8)0.0595 (10)0.0560 (11)−0.0091 (8)−0.0080 (8)−0.0148 (9)
C330.0414 (9)0.0513 (9)0.0466 (9)−0.0100 (7)−0.0075 (7)−0.0121 (8)
C340.0374 (8)0.0401 (8)0.0484 (9)−0.0041 (6)−0.0123 (7)−0.0102 (7)
C350.0385 (8)0.0449 (9)0.0500 (10)−0.0003 (7)−0.0125 (7)−0.0053 (8)
C360.0400 (9)0.0583 (11)0.0553 (11)0.0053 (8)−0.0097 (8)−0.0084 (9)
C370.0388 (8)0.0373 (8)0.0414 (9)−0.0016 (6)−0.0085 (7)−0.0076 (7)
C380.0456 (9)0.0488 (9)0.0565 (11)−0.0025 (7)−0.0192 (8)−0.0088 (8)
C390.0721 (14)0.0776 (14)0.0593 (13)−0.0055 (11)−0.0335 (11)−0.0023 (10)
C400.0891 (17)0.0597 (12)0.0755 (15)−0.0061 (12)−0.0310 (13)0.0124 (11)
C410.0710 (13)0.0423 (10)0.0718 (14)−0.0097 (9)−0.0142 (11)−0.0013 (9)
C420.0513 (10)0.0418 (9)0.0566 (11)−0.0050 (7)−0.0109 (8)−0.0133 (8)
O50.0816 (10)0.0369 (6)0.0617 (9)−0.0066 (6)0.0052 (7)−0.0120 (6)

Geometric parameters (Å, °)

S1—C101.745 (2)C6—H60.9300
S1—C111.7293 (19)C8—H80.9300
S2—C151.789 (2)C10—H100.9300
S2—C161.8411 (18)C12—H12B0.9700
S3—C321.738 (2)C12—H12A0.9700
S3—C311.743 (2)C15—H15B0.9700
S4—C371.8413 (17)C15—H15A0.9700
S4—C361.7929 (19)C17—H17B0.9700
O1—C131.214 (2)C17—H17A0.9700
O2—C141.209 (2)C18—H18B0.9700
O3—C341.216 (2)C18—H18A0.9700
O4—C351.218 (2)C19—H19A0.9700
O5—H5B0.848 (18)C19—H19B0.9700
O5—H5A0.833 (19)C20—H20A0.9700
N1—C111.366 (2)C20—H20B0.9700
N1—C81.377 (2)C21—H21A0.9700
N1—C91.395 (2)C21—H21B0.9700
N2—C111.311 (2)C22—C231.396 (3)
N2—C71.384 (2)C22—C271.384 (3)
N3—N41.3839 (19)C22—C281.467 (3)
N3—C131.345 (2)C23—C241.380 (3)
N4—C161.473 (2)C24—C251.362 (4)
N4—C141.368 (2)C25—C261.381 (4)
N3—H3A0.8600C26—C271.397 (4)
N5—C321.366 (2)C28—C291.371 (3)
N5—C291.379 (2)C30—C311.335 (3)
N5—C301.388 (2)C30—C331.485 (3)
N6—C321.306 (3)C33—C341.522 (2)
N6—C281.388 (3)C35—C361.494 (3)
N7—C341.342 (2)C37—C421.526 (2)
N7—N81.3845 (19)C37—C381.523 (3)
N8—C371.472 (2)C38—C391.525 (3)
N8—C351.346 (2)C39—C401.523 (3)
N7—H70.8600C40—C411.512 (3)
C1—C21.389 (3)C41—C421.524 (3)
C1—C71.471 (3)C23—H230.9300
C1—C61.388 (3)C24—H240.9300
C2—C31.397 (3)C25—H250.9300
C3—C41.368 (4)C26—H260.9300
C4—C51.363 (4)C27—H270.9300
C5—C61.385 (3)C29—H290.9300
C7—C81.364 (3)C31—H310.9300
C9—C101.330 (3)C33—H33A0.9700
C9—C121.486 (2)C33—H33B0.9700
C12—C131.517 (2)C36—H36B0.9700
C14—C151.491 (3)C36—H36A0.9700
C16—C171.519 (3)C38—H38A0.9700
C16—C211.521 (3)C38—H38B0.9700
C17—C181.522 (3)C39—H39A0.9700
C18—C191.507 (4)C39—H39B0.9700
C19—C201.513 (5)C40—H40B0.9700
C20—C211.525 (3)C40—H40A0.9700
C2—H20.9300C41—H41A0.9700
C3—H30.9300C41—H41B0.9700
C4—H40.9300C42—H42B0.9700
C5—H50.9300C42—H42A0.9700
S1···O2i3.3487 (17)C6···H82.9200
S1···N12.5482 (15)C8···H12B3.0400
S1···S1ii3.7967 (8)C8···H17A3.0600
S1···S3ii3.4544 (8)C8···H62.7600
S1···C10ii3.581 (2)C13···H12Av3.0000
S1···C31ii3.608 (2)C13···H5A2.906 (19)
S2···N42.5890 (14)C13···H17A2.8300
S2···C25iii3.655 (3)C17···H41Avi3.0200
S3···C10ii3.685 (2)C21···H3A3.0200
S3···O4i3.3109 (16)C21···H38B2.9500
S3···N52.5507 (16)C23···H15Aviii2.8600
S3···S1ii3.4544 (8)C23···H53.1000
S4···C3iv3.610 (3)C24···H15Aviii2.9000
S4···N82.6008 (14)C26···H15Bviii3.0000
S4···C2iv3.615 (2)C27···H292.9100
S1···H31ii3.1300C29···H272.7600
S2···H18A2.8700C29···H38A2.9800
S2···H20B2.8400C29···H33B3.0600
S3···H36Bi3.1600C32···H36Bi2.9400
S4···H41B2.7800C34···H38A3.0800
S4···H39A2.8700C34···H5Bv3.03 (2)
S4···H21A2.8300C35···H5Bv2.934 (17)
O1···N42.686 (2)C39···H19Bix3.0500
O1···O23.092 (2)C40···H19Bix3.0000
O1···C142.996 (2)C40···H17Bvii3.0600
O1···C173.159 (2)C41···H17Bvii2.8900
O1···O52.7097 (19)C42···H73.1000
O2···N32.724 (2)H2···N22.6200
O2···S1iv3.3487 (17)H3A···C213.0200
O2···O13.092 (2)H3A···O31.9800
O2···C133.082 (2)H3A···H12B2.1600
O2···C12v3.074 (2)H3A···H21B2.5600
O3···C353.122 (2)H5···C233.1000
O3···N32.841 (2)H5A···O11.880 (19)
O3···N82.711 (2)H5A···C132.906 (19)
O3···O43.215 (2)H5A···H7vi2.5400
O4···C10v3.306 (2)H5B···C34v3.03 (2)
O4···O5v2.764 (2)H5B···C35v2.934 (17)
O4···N72.713 (2)H5B···H7vi2.4600
O4···C343.121 (2)H5B···H33Bvi2.3900
O4···S3iv3.3109 (16)H5B···O4v1.917 (18)
O4···O33.215 (2)H6···C82.7600
O5···C34v3.331 (2)H6···H82.4000
O5···C33vi3.376 (2)H7···H5Bvii2.4600
O5···N7vi2.7617 (19)H7···H5Avii2.5400
O5···C33v3.349 (2)H7···C423.1000
O5···O12.7097 (19)H7···O5vii1.9400
O5···O4v2.764 (2)H7···H33B2.1700
O1···H17A2.8600H8···H62.4000
O1···H5A1.880 (19)H8···O32.8300
O1···H17B2.7900H8···C62.9200
O2···H12Av2.4800H10···O4v2.4100
O3···H82.8300H10···H12A2.5900
O3···H3A1.9800H12A···H102.5900
O3···H12B2.6200H12A···C13v3.0000
O4···H10v2.4100H12A···O2v2.4800
O4···H5Bv1.917 (18)H12B···O32.6200
O5···H33Bvi2.5400H12B···C83.0400
O5···H42Avi2.8300H12B···H3A2.1600
O5···H29vi2.9200H15A···C24iii2.9000
O5···H33Av2.7500H15A···C23iii2.8600
O5···H7vi1.9400H15B···C26iii3.0000
N1···S12.5482 (15)H15B···N2iv2.5700
N1···N22.237 (2)H17A···H21B2.5500
N2···N12.237 (2)H17A···C132.8300
N3···O22.724 (2)H17A···O12.8600
N3···O32.841 (2)H17A···N32.7100
N4···S22.5890 (14)H17A···C83.0600
N4···O12.686 (2)H17B···C40vi3.0600
N5···N62.237 (2)H17B···C41vi2.8900
N5···S32.5507 (16)H17B···H40Bvi2.5500
N6···C36i3.448 (3)H17B···O12.7900
N6···N52.237 (2)H17B···H41Avi2.2000
N7···O42.713 (2)H18A···S22.8700
N7···O5vii2.7617 (19)H19B···C39ix3.0500
N8···S42.6008 (14)H19B···H39Bix2.4700
N8···O32.711 (2)H19B···H40Aix2.4500
N2···H36Ai2.8400H19B···C40ix3.0000
N2···H15Bi2.5700H20B···S22.8400
N2···H22.6200H21A···S42.8300
N3···H17A2.7100H21B···N32.7300
N3···H21B2.7300H21B···H17A2.5500
N6···H36Bi2.5600H21B···H38B2.5200
N6···H232.6400H21B···H3A2.5600
N7···H42A2.9000H23···N62.6400
N7···H38A2.6400H27···C292.7600
C1···C36i3.521 (3)H27···H292.4000
C2···S4i3.615 (2)H29···C272.9100
C2···C36i3.519 (3)H29···H272.4000
C3···S4i3.610 (3)H29···H38A2.4400
C5···C233.417 (3)H29···O5vii2.9200
C8···C133.508 (2)H31···S1ii3.1300
C10···S1ii3.581 (2)H31···H33A2.5900
C10···O4v3.306 (2)H33A···H312.5900
C10···S3ii3.685 (2)H33A···O5v2.7500
C12···O2v3.074 (2)H33B···O5vii2.5400
C13···C83.508 (2)H33B···C293.0600
C13···C173.306 (2)H33B···H5Bvii2.3900
C13···O23.082 (2)H33B···H72.1700
C14···O12.996 (2)H36A···N2iv2.8400
C15···C24iii3.488 (3)H36B···C1iv3.0600
C15···C25iii3.465 (4)H36B···S3iv3.1600
C17···C133.306 (2)H36B···N6iv2.5600
C17···O13.159 (2)H36B···C32iv2.9400
C23···C53.417 (3)H38A···N72.6400
C24···C15viii3.488 (3)H38A···C292.9800
C25···C15viii3.465 (4)H38A···H292.4400
C25···S2viii3.655 (3)H38A···C343.0800
C29···C343.458 (3)H38B···C212.9500
C31···S1ii3.608 (2)H38B···H21B2.5200
C33···O5vii3.376 (2)H39A···C4ix2.8200
C33···O5v3.349 (2)H39A···S42.8700
C34···C383.457 (2)H39B···H19Bix2.4700
C34···O5v3.331 (2)H40A···H19Bix2.4500
C34···O43.121 (2)H40B···H17Bvii2.5500
C34···C293.458 (3)H40B···H42A2.5900
C35···O33.122 (2)H41A···C17vii3.0200
C36···C1iv3.521 (3)H41A···H17Bvii2.2000
C36···C2iv3.519 (3)H41B···S42.7800
C36···N6iv3.448 (3)H42A···N72.9000
C38···C343.457 (2)H42A···H40B2.5900
C1···H36Bi3.0600H42A···O5vii2.8300
C4···H39Aix2.8200
C10—S1—C1189.76 (9)C18—C19—H19B109.00
C15—S2—C1694.55 (9)C18—C19—H19A109.00
C31—S3—C3289.81 (10)H20A—C20—H20B108.00
C36—S4—C3793.69 (8)C19—C20—H20A109.00
H5A—O5—H5B110 (2)C21—C20—H20B109.00
C9—N1—C11115.26 (14)C21—C20—H20A109.00
C8—N1—C11106.06 (14)C19—C20—H20B109.00
C8—N1—C9138.60 (15)H21A—C21—H21B108.00
C7—N2—C11103.65 (16)C16—C21—H21A109.00
N4—N3—C13120.15 (14)C16—C21—H21B109.00
C14—N4—C16121.05 (14)C20—C21—H21B109.00
N3—N4—C16118.40 (13)C20—C21—H21A109.00
N3—N4—C14118.31 (13)C27—C22—C28121.11 (19)
C13—N3—H3A120.00C23—C22—C28120.73 (19)
N4—N3—H3A120.00C23—C22—C27118.1 (2)
C29—N5—C30138.38 (16)C22—C23—C24121.0 (2)
C30—N5—C32115.52 (15)C23—C24—C25120.4 (2)
C29—N5—C32106.09 (15)C24—C25—C26120.1 (3)
C28—N6—C32103.80 (16)C25—C26—C27119.9 (2)
N8—N7—C34119.88 (13)C22—C27—C26120.6 (2)
N7—N8—C37120.22 (13)C22—C28—C29126.78 (18)
N7—N8—C35119.23 (13)N6—C28—C29111.15 (17)
C35—N8—C37120.50 (14)N6—C28—C22121.99 (18)
N8—N7—H7120.00N5—C29—C28105.34 (16)
C34—N7—H7120.00N5—C30—C33119.68 (16)
C2—C1—C7120.74 (18)C31—C30—C33129.22 (18)
C6—C1—C7120.96 (18)N5—C30—C31111.08 (17)
C2—C1—C6118.30 (18)S3—C31—C30113.62 (15)
C1—C2—C3120.0 (2)N5—C32—N6113.62 (17)
C2—C3—C4120.7 (2)S3—C32—N5109.94 (14)
C3—C4—C5119.7 (2)S3—C32—N6136.44 (15)
C4—C5—C6120.6 (2)C30—C33—C34111.58 (15)
C1—C6—C5120.8 (2)N7—C34—C33114.61 (15)
N2—C7—C1121.12 (16)O3—C34—C33121.81 (16)
C1—C7—C8127.44 (17)O3—C34—N7123.55 (16)
N2—C7—C8111.42 (15)N8—C35—C36111.73 (15)
N1—C8—C7105.50 (15)O4—C35—N8124.10 (17)
C10—C9—C12129.00 (17)O4—C35—C36124.17 (17)
N1—C9—C12120.05 (15)S4—C36—C35108.23 (13)
N1—C9—C10110.83 (16)N8—C37—C38111.38 (14)
S1—C10—C9113.87 (15)S4—C37—C38110.84 (12)
S1—C11—N2136.35 (16)S4—C37—C42109.67 (12)
S1—C11—N1110.25 (13)S4—C37—N8102.87 (11)
N1—C11—N2113.38 (16)N8—C37—C42110.98 (13)
C9—C12—C13109.81 (14)C38—C37—C42110.85 (14)
O1—C13—N3121.85 (16)C37—C38—C39111.58 (16)
N3—C13—C12114.82 (15)C38—C39—C40111.30 (18)
O1—C13—C12123.31 (16)C39—C40—C41111.23 (19)
O2—C14—N4124.47 (18)C40—C41—C42111.33 (18)
N4—C14—C15110.82 (16)C37—C42—C41110.31 (15)
O2—C14—C15124.72 (19)C24—C23—H23120.00
S2—C15—C14108.78 (15)C22—C23—H23119.00
C17—C16—C21109.66 (15)C23—C24—H24120.00
N4—C16—C17112.39 (14)C25—C24—H24120.00
N4—C16—C21110.48 (14)C26—C25—H25120.00
S2—C16—C17111.81 (12)C24—C25—H25120.00
S2—C16—N4102.18 (11)C25—C26—H26120.00
S2—C16—C21110.13 (13)C27—C26—H26120.00
C16—C17—C18111.68 (16)C26—C27—H27120.00
C17—C18—C19111.47 (19)C22—C27—H27120.00
C18—C19—C20111.3 (2)N5—C29—H29127.00
C19—C20—C21111.4 (2)C28—C29—H29127.00
C16—C21—C20111.24 (17)C30—C31—H31123.00
C1—C2—H2120.00S3—C31—H31123.00
C3—C2—H2120.00C30—C33—H33A109.00
C4—C3—H3120.00C34—C33—H33A109.00
C2—C3—H3120.00C34—C33—H33B109.00
C3—C4—H4120.00C30—C33—H33B109.00
C5—C4—H4120.00H33A—C33—H33B108.00
C6—C5—H5120.00S4—C36—H36B110.00
C4—C5—H5120.00C35—C36—H36A110.00
C5—C6—H6120.00C35—C36—H36B110.00
C1—C6—H6120.00H36A—C36—H36B108.00
N1—C8—H8127.00S4—C36—H36A110.00
C7—C8—H8127.00C37—C38—H38B109.00
C9—C10—H10123.00C39—C38—H38A109.00
S1—C10—H10123.00C37—C38—H38A109.00
C13—C12—H12B110.00H38A—C38—H38B108.00
C9—C12—H12B110.00C39—C38—H38B109.00
H12A—C12—H12B108.00C38—C39—H39A109.00
C13—C12—H12A110.00C38—C39—H39B109.00
C9—C12—H12A110.00C40—C39—H39B109.00
S2—C15—H15B110.00H39A—C39—H39B108.00
C14—C15—H15A110.00C40—C39—H39A109.00
C14—C15—H15B110.00C39—C40—H40B109.00
H15A—C15—H15B108.00C41—C40—H40A109.00
S2—C15—H15A110.00C41—C40—H40B109.00
C18—C17—H17B109.00H40A—C40—H40B108.00
C16—C17—H17B109.00C39—C40—H40A109.00
H17A—C17—H17B108.00C40—C41—H41B109.00
C18—C17—H17A109.00C42—C41—H41A109.00
C16—C17—H17A109.00C40—C41—H41A109.00
C19—C18—H18A109.00H41A—C41—H41B108.00
C17—C18—H18B109.00C42—C41—H41B109.00
C17—C18—H18A109.00C37—C42—H42A110.00
C19—C18—H18B109.00C37—C42—H42B110.00
H18A—C18—H18B108.00C41—C42—H42B110.00
C20—C19—H19A109.00H42A—C42—H42B108.00
C20—C19—H19B109.00C41—C42—H42A110.00
H19A—C19—H19B108.00
C10—S1—C11—N2176.9 (2)C37—N8—C35—O4174.60 (17)
C10—S1—C11—N1−1.42 (14)C37—N8—C35—C36−5.0 (2)
C11—S1—C10—C90.62 (16)N7—N8—C37—S4−167.85 (11)
C15—S2—C16—N414.50 (13)C6—C1—C7—N2163.05 (18)
C16—S2—C15—C14−11.71 (16)C2—C1—C7—C8160.2 (2)
C15—S2—C16—C17−105.91 (14)C2—C1—C7—N2−17.7 (3)
C15—S2—C16—C21131.92 (14)C7—C1—C6—C5178.9 (2)
C31—S3—C32—N6178.7 (2)C6—C1—C2—C30.0 (3)
C32—S3—C31—C300.70 (16)C7—C1—C2—C3−179.3 (2)
C31—S3—C32—N5−1.50 (15)C2—C1—C6—C5−0.3 (3)
C37—S4—C36—C3514.05 (14)C6—C1—C7—C8−19.0 (3)
C36—S4—C37—C42102.61 (13)C1—C2—C3—C40.4 (4)
C36—S4—C37—N8−15.53 (12)C2—C3—C4—C5−0.4 (4)
C36—S4—C37—C38−134.68 (13)C3—C4—C5—C60.0 (4)
C9—N1—C11—N2−176.73 (15)C4—C5—C6—C10.3 (4)
C8—N1—C11—S1179.35 (12)N2—C7—C8—N10.7 (2)
C11—N1—C9—C12174.83 (15)C1—C7—C8—N1−177.46 (17)
C11—N1—C8—C7−0.77 (18)C10—C9—C12—C13103.4 (2)
C8—N1—C9—C10−177.71 (19)C12—C9—C10—S1−175.59 (15)
C9—N1—C11—S11.97 (19)N1—C9—C12—C13−72.2 (2)
C8—N1—C9—C12−1.4 (3)N1—C9—C10—S10.4 (2)
C8—N1—C11—N20.7 (2)C9—C12—C13—N3117.53 (17)
C11—N1—C9—C10−1.5 (2)C9—C12—C13—O1−61.1 (2)
C9—N1—C8—C7175.65 (18)N4—C14—C15—S24.7 (2)
C11—N2—C7—C1177.98 (17)O2—C14—C15—S2−175.19 (19)
C11—N2—C7—C8−0.3 (2)N4—C16—C21—C20179.11 (19)
C7—N2—C11—N1−0.2 (2)N4—C16—C17—C18179.80 (15)
C7—N2—C11—S1−178.47 (17)C17—C16—C21—C20−56.5 (2)
N4—N3—C13—O1−2.2 (2)S2—C16—C21—C2067.0 (2)
N4—N3—C13—C12179.16 (14)S2—C16—C17—C18−65.96 (18)
C13—N3—N4—C1696.51 (18)C21—C16—C17—C1856.5 (2)
C13—N3—N4—C14−66.7 (2)C16—C17—C18—C19−56.0 (3)
C16—N4—C14—O2−172.19 (19)C17—C18—C19—C2054.4 (3)
N3—N4—C14—C15170.62 (16)C18—C19—C20—C21−54.6 (3)
N3—N4—C16—C17−58.36 (19)C19—C20—C21—C1656.1 (3)
C14—N4—C16—C21−132.82 (18)C23—C22—C28—C29157.0 (2)
C14—N4—C16—C17104.34 (19)C27—C22—C28—C29−20.6 (3)
C14—N4—C16—S2−15.66 (19)C27—C22—C28—N6163.0 (2)
N3—N4—C14—O2−9.5 (3)C27—C22—C23—C240.4 (3)
N3—N4—C16—C2164.5 (2)C23—C22—C28—N6−19.3 (3)
N3—N4—C16—S2−178.36 (12)C23—C22—C27—C26−0.4 (3)
C16—N4—C14—C157.9 (2)C28—C22—C27—C26177.3 (2)
C32—N5—C30—C33176.91 (16)C28—C22—C23—C24−177.4 (2)
C30—N5—C32—N6−178.10 (16)C22—C23—C24—C250.2 (4)
C29—N5—C32—S3−179.06 (12)C23—C24—C25—C26−0.7 (4)
C30—N5—C32—S32.0 (2)C24—C25—C26—C270.7 (4)
C29—N5—C32—N60.8 (2)C25—C26—C27—C22−0.1 (4)
C29—N5—C30—C33−1.5 (3)N6—C28—C29—N50.7 (2)
C32—N5—C30—C31−1.5 (2)C22—C28—C29—N5−176.02 (18)
C32—N5—C29—C28−0.9 (2)C31—C30—C33—C34109.4 (2)
C30—N5—C29—C28177.7 (2)N5—C30—C31—S30.3 (2)
C29—N5—C30—C31−180.0 (2)N5—C30—C33—C34−68.7 (2)
C28—N6—C32—N5−0.4 (2)C33—C30—C31—S3−177.96 (16)
C32—N6—C28—C22176.68 (18)C30—C33—C34—N7132.25 (16)
C28—N6—C32—S3179.43 (18)C30—C33—C34—O3−49.7 (2)
C32—N6—C28—C29−0.2 (2)O4—C35—C36—S4172.38 (16)
N8—N7—C34—O3−3.4 (3)N8—C35—C36—S4−8.03 (19)
C34—N7—N8—C37109.47 (17)S4—C37—C38—C39−66.61 (18)
N8—N7—C34—C33174.63 (14)N8—C37—C38—C39179.50 (15)
C34—N7—N8—C35−73.1 (2)C42—C37—C38—C3955.4 (2)
N7—N8—C35—C36177.60 (14)S4—C37—C42—C4166.18 (18)
N7—N8—C35—O4−2.8 (3)N8—C37—C42—C41179.15 (15)
C35—N8—C37—S414.76 (18)C38—C37—C42—C41−56.5 (2)
C35—N8—C37—C38133.53 (16)C37—C38—C39—C40−54.3 (2)
N7—N8—C37—C38−49.08 (19)C38—C39—C40—C4154.6 (2)
C35—N8—C37—C42−102.45 (18)C39—C40—C41—C42−56.4 (2)
N7—N8—C37—C4274.93 (19)C40—C41—C42—C3757.3 (2)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O30.861.982.841 (2)175
O5—H5A···O10.833 (19)1.880 (19)2.7097 (19)174.4 (18)
O5—H5B···O4v0.848 (18)1.917 (18)2.764 (2)177 (2)
N7—H7···O5vii0.861.942.7617 (19)160
C10—H10···O4v0.932.413.306 (2)161
C12—H12A···O2v0.972.483.074 (2)120
C15—H15B···N2iv0.972.573.462 (3)153
C18—H18A···S20.972.873.255 (2)105
C20—H20B···S20.972.843.227 (3)105
C21—H21A···S40.972.833.768 (2)163
C33—H33B···O5vii0.972.543.376 (2)144
C36—H36B···N6iv0.972.563.448 (3)153
C39—H39A···S40.972.873.246 (2)104
C41—H41B···S40.972.783.194 (2)106

Symmetry codes: (v) −x+1, −y, −z+2; (vii) x, y+1, z; (iv) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2390).

References

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