organic compounds
N-(3-Oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-6-phenylimidazo[2,1-b][1,3]thiazole-3-acetamide hemihydrate
aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Istanbul, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
The title compound, C21H22N4O2S2·0.5H2O, crystallizes with two molecules in the 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 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, 2007); Allen et al. (1987); Amarouch et al. (1988); Andreani et al. (1998); Cremer & Pople (1975); Devlin & Hargrave (1989); Gürsoy & Ulusoy Güzeldemirci (2007); Srimanth et al. (2002); Ulusoy (2002); Ur et al. (2004); Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Büyükgüngör (2005); Öztürk Yıldırım, Akkurt, Ur, Cesur, Cesur & Heinemann (2005).
Experimental
Crystal data
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536808009306/hg2390sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009306/hg2390Isup2.hkl
A mixture of 6-phenyl-N-(cyclohexylidene)imidazo[2,1-b]thiazole-3-αcetohydrazide (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%.
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).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).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. |
C21H22N4O2S2·0.5H2O | Z = 4 |
Mr = 435.58 | F(000) = 916 |
Triclinic, P1 | Dx = 1.359 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0175 (3) Å | Cell parameters from 51089 reflections |
b = 11.8817 (3) Å | θ = 1.8–28.0° |
c = 17.6162 (5) Å | µ = 0.28 mm−1 |
α = 75.123 (2)° | T = 296 K |
β = 73.502 (2)° | Block, colourless |
γ = 81.012 (2)° | 0.52 × 0.39 × 0.25 mm |
V = 2128.36 (10) Å3 |
Stoe IPDS2 diffractometer | 8351 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 6705 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.054 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −13→13 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.869, Tmax = 0.934 | l = −21→21 |
38012 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.3604P] where P = (Fo2 + 2Fc2)/3 |
8351 reflections | (Δ/σ)max = 0.001 |
538 parameters | Δρmax = 0.29 e Å−3 |
3 restraints | Δρmin = −0.34 e Å−3 |
C21H22N4O2S2·0.5H2O | γ = 81.012 (2)° |
Mr = 435.58 | V = 2128.36 (10) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.0175 (3) Å | Mo Kα radiation |
b = 11.8817 (3) Å | µ = 0.28 mm−1 |
c = 17.6162 (5) Å | T = 296 K |
α = 75.123 (2)° | 0.52 × 0.39 × 0.25 mm |
β = 73.502 (2)° |
Stoe IPDS2 diffractometer | 8351 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 6705 reflections with I > 2σ(I) |
Tmin = 0.869, Tmax = 0.934 | Rint = 0.054 |
38012 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 3 restraints |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.29 e Å−3 |
8351 reflections | Δρmin = −0.34 e Å−3 |
538 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.05906 (5) | −0.07649 (4) | 0.91226 (4) | 0.0650 (2) | |
S2 | 0.82255 (5) | 0.06276 (5) | 0.64335 (3) | 0.0633 (2) | |
O1 | 0.51521 (13) | −0.09814 (10) | 0.86877 (9) | 0.0613 (4) | |
O2 | 0.77147 (14) | −0.03089 (17) | 0.87525 (9) | 0.0824 (6) | |
N1 | 0.21182 (12) | 0.08291 (11) | 0.86246 (8) | 0.0406 (4) | |
N2 | 0.07989 (15) | 0.12137 (13) | 0.78125 (9) | 0.0525 (5) | |
N3 | 0.55426 (12) | 0.08920 (12) | 0.84165 (8) | 0.0423 (4) | |
N4 | 0.66458 (12) | 0.07339 (12) | 0.78224 (8) | 0.0438 (4) | |
C1 | 0.16656 (17) | 0.29982 (16) | 0.68388 (11) | 0.0506 (5) | |
C2 | 0.1063 (2) | 0.2917 (2) | 0.62638 (12) | 0.0639 (7) | |
C3 | 0.1088 (2) | 0.3821 (3) | 0.55737 (14) | 0.0811 (9) | |
C4 | 0.1708 (3) | 0.4788 (2) | 0.54542 (14) | 0.0822 (9) | |
C5 | 0.2302 (2) | 0.4874 (2) | 0.60160 (15) | 0.0767 (8) | |
C6 | 0.2283 (2) | 0.39910 (17) | 0.67062 (13) | 0.0632 (7) | |
C7 | 0.16624 (16) | 0.20488 (15) | 0.75640 (10) | 0.0457 (5) | |
C8 | 0.24710 (16) | 0.18353 (14) | 0.80548 (10) | 0.0437 (5) | |
C9 | 0.25238 (15) | 0.00677 (14) | 0.92704 (10) | 0.0418 (5) | |
C10 | 0.17980 (17) | −0.08177 (16) | 0.95955 (12) | 0.0526 (6) | |
C11 | 0.11095 (17) | 0.05086 (15) | 0.84477 (11) | 0.0476 (5) | |
C12 | 0.36795 (15) | 0.02720 (16) | 0.94737 (10) | 0.0443 (5) | |
C13 | 0.48551 (15) | −0.00160 (14) | 0.88323 (10) | 0.0410 (5) | |
C14 | 0.76563 (16) | 0.00525 (18) | 0.80555 (11) | 0.0526 (6) | |
C15 | 0.86737 (18) | −0.0181 (2) | 0.73343 (12) | 0.0615 (7) | |
C16 | 0.65776 (15) | 0.10149 (14) | 0.69704 (10) | 0.0415 (5) | |
C17 | 0.56447 (17) | 0.03156 (16) | 0.68369 (11) | 0.0494 (6) | |
C18 | 0.5583 (2) | 0.0620 (2) | 0.59546 (13) | 0.0697 (8) | |
C19 | 0.5257 (3) | 0.1911 (3) | 0.56671 (16) | 0.0926 (10) | |
C20 | 0.6163 (3) | 0.2626 (2) | 0.58065 (15) | 0.0890 (9) | |
C21 | 0.6218 (2) | 0.23148 (16) | 0.66925 (13) | 0.0635 (7) | |
S3 | 0.00085 (5) | 0.34118 (5) | 0.95204 (3) | 0.0644 (2) | |
S4 | 0.80682 (4) | 0.45925 (4) | 0.68876 (3) | 0.0499 (1) | |
O3 | 0.45903 (13) | 0.30931 (11) | 0.88067 (9) | 0.0627 (5) | |
O4 | 0.72609 (13) | 0.31913 (13) | 0.91780 (8) | 0.0676 (5) | |
N5 | 0.16872 (13) | 0.48752 (12) | 0.89897 (9) | 0.0461 (5) | |
N6 | 0.02651 (14) | 0.54441 (14) | 0.82469 (10) | 0.0563 (5) | |
N7 | 0.52947 (12) | 0.47506 (11) | 0.88527 (8) | 0.0395 (4) | |
N8 | 0.64254 (12) | 0.45960 (11) | 0.82786 (8) | 0.0415 (4) | |
C22 | 0.12270 (18) | 0.72081 (17) | 0.72858 (12) | 0.0572 (6) | |
C23 | 0.0572 (2) | 0.7221 (2) | 0.67113 (13) | 0.0662 (7) | |
C24 | 0.0637 (2) | 0.8126 (2) | 0.60334 (15) | 0.0811 (9) | |
C25 | 0.1349 (3) | 0.9027 (3) | 0.59114 (15) | 0.0872 (9) | |
C26 | 0.2000 (2) | 0.9046 (2) | 0.64714 (17) | 0.0863 (9) | |
C27 | 0.1938 (2) | 0.81328 (19) | 0.71592 (15) | 0.0714 (8) | |
C28 | 0.11981 (17) | 0.62186 (16) | 0.79871 (12) | 0.0518 (6) | |
C29 | 0.20755 (16) | 0.58894 (15) | 0.84390 (11) | 0.0494 (6) | |
C30 | 0.20970 (16) | 0.40507 (15) | 0.96034 (11) | 0.0459 (5) | |
C31 | 0.12971 (18) | 0.32183 (17) | 0.99445 (12) | 0.0559 (6) | |
C32 | 0.05979 (16) | 0.46679 (16) | 0.88438 (12) | 0.0508 (6) | |
C33 | 0.33060 (15) | 0.41641 (16) | 0.97807 (11) | 0.0464 (5) | |
C34 | 0.44507 (15) | 0.39476 (14) | 0.90929 (10) | 0.0416 (5) | |
C35 | 0.73393 (15) | 0.37844 (15) | 0.84930 (11) | 0.0456 (5) | |
C36 | 0.84643 (17) | 0.37065 (17) | 0.77895 (11) | 0.0537 (6) | |
C37 | 0.66435 (15) | 0.53459 (13) | 0.74539 (10) | 0.0400 (5) | |
C38 | 0.55215 (17) | 0.54151 (16) | 0.70950 (11) | 0.0498 (6) | |
C39 | 0.5738 (2) | 0.6200 (2) | 0.62431 (13) | 0.0687 (8) | |
C40 | 0.6054 (2) | 0.74073 (19) | 0.62337 (15) | 0.0780 (9) | |
C41 | 0.7171 (2) | 0.73238 (17) | 0.65896 (13) | 0.0642 (7) | |
C42 | 0.69282 (18) | 0.65648 (15) | 0.74490 (11) | 0.0500 (6) | |
O5 | 0.43460 (15) | −0.31518 (11) | 0.92938 (9) | 0.0647 (5) | |
H2 | 0.06420 | 0.22620 | 0.63380 | 0.0770* | |
H3 | 0.06790 | 0.37640 | 0.51920 | 0.0970* | |
H3A | 0.52960 | 0.15720 | 0.85200 | 0.0510* | |
H4 | 0.17250 | 0.53850 | 0.49920 | 0.0990* | |
H5 | 0.27230 | 0.55310 | 0.59350 | 0.0920* | |
H6 | 0.26880 | 0.40640 | 0.70860 | 0.0760* | |
H8 | 0.31230 | 0.22760 | 0.80130 | 0.0520* | |
H10 | 0.19230 | −0.14110 | 1.00350 | 0.0630* | |
H12A | 0.37230 | −0.02150 | 1.00010 | 0.0530* | |
H12B | 0.36380 | 0.10830 | 0.95000 | 0.0530* | |
H15A | 0.87850 | −0.10100 | 0.73440 | 0.0740* | |
H15B | 0.94720 | 0.00540 | 0.73440 | 0.0740* | |
H17A | 0.48060 | 0.04730 | 0.71810 | 0.0590* | |
H17B | 0.59000 | −0.05120 | 0.69930 | 0.0590* | |
H18A | 0.63970 | 0.03850 | 0.56170 | 0.0840* | |
H18B | 0.49470 | 0.01890 | 0.58990 | 0.0840* | |
H19A | 0.43950 | 0.21250 | 0.59560 | 0.1110* | |
H19B | 0.52940 | 0.20850 | 0.50920 | 0.1110* | |
H20A | 0.58890 | 0.34510 | 0.56550 | 0.1070* | |
H20B | 0.70060 | 0.24870 | 0.54630 | 0.1070* | |
H21A | 0.68380 | 0.27570 | 0.67560 | 0.0760* | |
H21B | 0.53950 | 0.25290 | 0.70310 | 0.0760* | |
H7 | 0.51340 | 0.53600 | 0.90550 | 0.0470* | |
H23 | 0.00840 | 0.66110 | 0.67870 | 0.0790* | |
H24 | 0.01920 | 0.81210 | 0.56580 | 0.0970* | |
H25 | 0.13970 | 0.96300 | 0.54500 | 0.1050* | |
H26 | 0.24780 | 0.96650 | 0.63910 | 0.1040* | |
H27 | 0.23780 | 0.81470 | 0.75350 | 0.0860* | |
H29 | 0.27820 | 0.62690 | 0.83850 | 0.0590* | |
H31 | 0.14160 | 0.25940 | 1.03680 | 0.0670* | |
H33A | 0.33810 | 0.36070 | 1.02790 | 0.0560* | |
H33B | 0.32930 | 0.49430 | 0.98620 | 0.0560* | |
H36A | 0.86810 | 0.29010 | 0.77390 | 0.0640* | |
H36B | 0.91910 | 0.39830 | 0.78710 | 0.0640* | |
H38A | 0.47580 | 0.57180 | 0.74450 | 0.0600* | |
H38B | 0.53930 | 0.46360 | 0.70730 | 0.0600* | |
H39A | 0.64310 | 0.58420 | 0.58760 | 0.0830* | |
H39B | 0.49800 | 0.62780 | 0.60520 | 0.0830* | |
H40A | 0.62520 | 0.78650 | 0.56790 | 0.0940* | |
H40B | 0.53200 | 0.78060 | 0.65450 | 0.0940* | |
H41A | 0.73250 | 0.81020 | 0.65990 | 0.0770* | |
H41B | 0.79260 | 0.69940 | 0.62480 | 0.0770* | |
H42A | 0.62140 | 0.69240 | 0.78020 | 0.0600* | |
H42B | 0.76690 | 0.65050 | 0.76550 | 0.0600* | |
H5A | 0.459 (2) | −0.2488 (15) | 0.9077 (12) | 0.0750* | |
H5B | 0.384 (2) | −0.3144 (19) | 0.9756 (10) | 0.0750* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0629 (3) | 0.0560 (3) | 0.0770 (4) | −0.0232 (2) | −0.0327 (3) | 0.0105 (2) |
S2 | 0.0430 (2) | 0.0949 (4) | 0.0429 (3) | −0.0046 (2) | 0.0006 (2) | −0.0132 (2) |
O1 | 0.0593 (8) | 0.0384 (6) | 0.0690 (9) | −0.0023 (6) | 0.0044 (7) | −0.0063 (6) |
O2 | 0.0527 (8) | 0.1431 (15) | 0.0474 (8) | 0.0145 (9) | −0.0170 (7) | −0.0237 (9) |
N1 | 0.0368 (7) | 0.0405 (7) | 0.0420 (7) | −0.0023 (5) | −0.0119 (6) | −0.0036 (6) |
N2 | 0.0518 (9) | 0.0530 (8) | 0.0545 (9) | −0.0033 (7) | −0.0239 (7) | −0.0044 (7) |
N3 | 0.0376 (7) | 0.0424 (7) | 0.0424 (7) | −0.0032 (6) | −0.0002 (6) | −0.0128 (6) |
N4 | 0.0356 (7) | 0.0531 (8) | 0.0401 (7) | −0.0056 (6) | −0.0024 (6) | −0.0130 (6) |
C1 | 0.0442 (9) | 0.0545 (10) | 0.0407 (9) | 0.0109 (8) | −0.0059 (7) | −0.0035 (8) |
C2 | 0.0599 (12) | 0.0743 (13) | 0.0494 (11) | 0.0076 (10) | −0.0155 (9) | −0.0060 (10) |
C3 | 0.0772 (15) | 0.1069 (19) | 0.0469 (12) | 0.0196 (14) | −0.0211 (11) | −0.0067 (12) |
C4 | 0.0858 (17) | 0.0768 (15) | 0.0532 (13) | 0.0167 (13) | −0.0061 (12) | 0.0121 (11) |
C5 | 0.0836 (16) | 0.0564 (12) | 0.0642 (14) | 0.0056 (11) | −0.0017 (12) | 0.0056 (10) |
C6 | 0.0681 (13) | 0.0525 (11) | 0.0566 (12) | 0.0034 (9) | −0.0112 (10) | −0.0011 (9) |
C7 | 0.0420 (9) | 0.0455 (9) | 0.0447 (9) | 0.0026 (7) | −0.0103 (7) | −0.0063 (7) |
C8 | 0.0401 (8) | 0.0418 (8) | 0.0443 (9) | −0.0037 (7) | −0.0098 (7) | −0.0023 (7) |
C9 | 0.0362 (8) | 0.0467 (9) | 0.0363 (8) | 0.0013 (7) | −0.0081 (6) | −0.0030 (7) |
C10 | 0.0452 (9) | 0.0513 (10) | 0.0549 (11) | −0.0054 (8) | −0.0166 (8) | 0.0043 (8) |
C11 | 0.0452 (9) | 0.0448 (9) | 0.0539 (10) | −0.0060 (7) | −0.0192 (8) | −0.0048 (8) |
C12 | 0.0349 (8) | 0.0588 (10) | 0.0346 (8) | −0.0031 (7) | −0.0070 (6) | −0.0053 (7) |
C13 | 0.0359 (8) | 0.0446 (9) | 0.0378 (8) | −0.0011 (7) | −0.0094 (6) | −0.0028 (7) |
C14 | 0.0363 (9) | 0.0787 (12) | 0.0448 (10) | −0.0029 (8) | −0.0096 (7) | −0.0198 (9) |
C15 | 0.0402 (9) | 0.0950 (15) | 0.0507 (11) | 0.0047 (9) | −0.0099 (8) | −0.0272 (10) |
C16 | 0.0402 (8) | 0.0405 (8) | 0.0401 (9) | −0.0058 (7) | −0.0038 (7) | −0.0087 (7) |
C17 | 0.0485 (10) | 0.0514 (10) | 0.0506 (10) | −0.0054 (8) | −0.0127 (8) | −0.0148 (8) |
C18 | 0.0665 (13) | 0.0924 (16) | 0.0579 (13) | −0.0055 (12) | −0.0232 (10) | −0.0230 (11) |
C19 | 0.0980 (19) | 0.112 (2) | 0.0586 (14) | 0.0179 (17) | −0.0357 (14) | −0.0017 (14) |
C20 | 0.113 (2) | 0.0595 (13) | 0.0659 (15) | 0.0046 (13) | −0.0101 (14) | 0.0143 (11) |
C21 | 0.0802 (14) | 0.0389 (9) | 0.0608 (12) | −0.0082 (9) | −0.0071 (10) | −0.0029 (8) |
S3 | 0.0473 (3) | 0.0729 (3) | 0.0725 (3) | −0.0255 (2) | −0.0150 (2) | −0.0040 (3) |
S4 | 0.0475 (2) | 0.0523 (2) | 0.0451 (2) | 0.0038 (2) | −0.0066 (2) | −0.0133 (2) |
O3 | 0.0584 (8) | 0.0493 (7) | 0.0831 (10) | −0.0109 (6) | −0.0039 (7) | −0.0319 (7) |
O4 | 0.0530 (8) | 0.0756 (9) | 0.0524 (8) | 0.0118 (7) | −0.0103 (6) | 0.0098 (7) |
N5 | 0.0353 (7) | 0.0495 (8) | 0.0531 (9) | −0.0066 (6) | −0.0074 (6) | −0.0136 (7) |
N6 | 0.0440 (8) | 0.0646 (10) | 0.0600 (10) | −0.0044 (7) | −0.0123 (7) | −0.0148 (8) |
N7 | 0.0353 (7) | 0.0365 (7) | 0.0453 (8) | −0.0025 (5) | −0.0061 (6) | −0.0120 (6) |
N8 | 0.0345 (7) | 0.0412 (7) | 0.0433 (7) | 0.0005 (5) | −0.0063 (6) | −0.0060 (6) |
C22 | 0.0445 (10) | 0.0602 (11) | 0.0560 (11) | 0.0065 (8) | −0.0009 (8) | −0.0137 (9) |
C23 | 0.0595 (12) | 0.0724 (13) | 0.0585 (13) | 0.0107 (10) | −0.0097 (10) | −0.0160 (10) |
C24 | 0.0741 (15) | 0.0959 (18) | 0.0574 (14) | 0.0163 (14) | −0.0077 (11) | −0.0139 (13) |
C25 | 0.0711 (15) | 0.0965 (19) | 0.0581 (14) | 0.0143 (14) | 0.0064 (12) | 0.0069 (13) |
C26 | 0.0650 (14) | 0.0745 (15) | 0.0913 (19) | −0.0087 (12) | 0.0080 (14) | 0.0007 (13) |
C27 | 0.0578 (12) | 0.0701 (13) | 0.0724 (14) | −0.0005 (10) | −0.0078 (10) | −0.0044 (11) |
C28 | 0.0431 (9) | 0.0535 (10) | 0.0553 (11) | 0.0015 (8) | −0.0060 (8) | −0.0168 (8) |
C29 | 0.0397 (9) | 0.0477 (9) | 0.0575 (11) | −0.0054 (7) | −0.0065 (8) | −0.0116 (8) |
C30 | 0.0387 (8) | 0.0503 (9) | 0.0476 (10) | −0.0081 (7) | −0.0056 (7) | −0.0128 (8) |
C31 | 0.0472 (10) | 0.0613 (11) | 0.0568 (11) | −0.0165 (8) | −0.0096 (8) | −0.0063 (9) |
C32 | 0.0371 (8) | 0.0595 (10) | 0.0560 (11) | −0.0091 (8) | −0.0080 (8) | −0.0148 (9) |
C33 | 0.0414 (9) | 0.0513 (9) | 0.0466 (9) | −0.0100 (7) | −0.0075 (7) | −0.0121 (8) |
C34 | 0.0374 (8) | 0.0401 (8) | 0.0484 (9) | −0.0041 (6) | −0.0123 (7) | −0.0102 (7) |
C35 | 0.0385 (8) | 0.0449 (9) | 0.0500 (10) | −0.0003 (7) | −0.0125 (7) | −0.0053 (8) |
C36 | 0.0400 (9) | 0.0583 (11) | 0.0553 (11) | 0.0053 (8) | −0.0097 (8) | −0.0084 (9) |
C37 | 0.0388 (8) | 0.0373 (8) | 0.0414 (9) | −0.0016 (6) | −0.0085 (7) | −0.0076 (7) |
C38 | 0.0456 (9) | 0.0488 (9) | 0.0565 (11) | −0.0025 (7) | −0.0192 (8) | −0.0088 (8) |
C39 | 0.0721 (14) | 0.0776 (14) | 0.0593 (13) | −0.0055 (11) | −0.0335 (11) | −0.0023 (10) |
C40 | 0.0891 (17) | 0.0597 (12) | 0.0755 (15) | −0.0061 (12) | −0.0310 (13) | 0.0124 (11) |
C41 | 0.0710 (13) | 0.0423 (10) | 0.0718 (14) | −0.0097 (9) | −0.0142 (11) | −0.0013 (9) |
C42 | 0.0513 (10) | 0.0418 (9) | 0.0566 (11) | −0.0050 (7) | −0.0109 (8) | −0.0133 (8) |
O5 | 0.0816 (10) | 0.0369 (6) | 0.0617 (9) | −0.0066 (6) | 0.0052 (7) | −0.0120 (6) |
S1—C10 | 1.745 (2) | C6—H6 | 0.9300 |
S1—C11 | 1.7293 (19) | C8—H8 | 0.9300 |
S2—C15 | 1.789 (2) | C10—H10 | 0.9300 |
S2—C16 | 1.8411 (18) | C12—H12B | 0.9700 |
S3—C32 | 1.738 (2) | C12—H12A | 0.9700 |
S3—C31 | 1.743 (2) | C15—H15B | 0.9700 |
S4—C37 | 1.8413 (17) | C15—H15A | 0.9700 |
S4—C36 | 1.7929 (19) | C17—H17B | 0.9700 |
O1—C13 | 1.214 (2) | C17—H17A | 0.9700 |
O2—C14 | 1.209 (2) | C18—H18B | 0.9700 |
O3—C34 | 1.216 (2) | C18—H18A | 0.9700 |
O4—C35 | 1.218 (2) | C19—H19A | 0.9700 |
O5—H5B | 0.848 (18) | C19—H19B | 0.9700 |
O5—H5A | 0.833 (19) | C20—H20A | 0.9700 |
N1—C11 | 1.366 (2) | C20—H20B | 0.9700 |
N1—C8 | 1.377 (2) | C21—H21A | 0.9700 |
N1—C9 | 1.395 (2) | C21—H21B | 0.9700 |
N2—C11 | 1.311 (2) | C22—C23 | 1.396 (3) |
N2—C7 | 1.384 (2) | C22—C27 | 1.384 (3) |
N3—N4 | 1.3839 (19) | C22—C28 | 1.467 (3) |
N3—C13 | 1.345 (2) | C23—C24 | 1.380 (3) |
N4—C16 | 1.473 (2) | C24—C25 | 1.362 (4) |
N4—C14 | 1.368 (2) | C25—C26 | 1.381 (4) |
N3—H3A | 0.8600 | C26—C27 | 1.397 (4) |
N5—C32 | 1.366 (2) | C28—C29 | 1.371 (3) |
N5—C29 | 1.379 (2) | C30—C31 | 1.335 (3) |
N5—C30 | 1.388 (2) | C30—C33 | 1.485 (3) |
N6—C32 | 1.306 (3) | C33—C34 | 1.522 (2) |
N6—C28 | 1.388 (3) | C35—C36 | 1.494 (3) |
N7—C34 | 1.342 (2) | C37—C42 | 1.526 (2) |
N7—N8 | 1.3845 (19) | C37—C38 | 1.523 (3) |
N8—C37 | 1.472 (2) | C38—C39 | 1.525 (3) |
N8—C35 | 1.346 (2) | C39—C40 | 1.523 (3) |
N7—H7 | 0.8600 | C40—C41 | 1.512 (3) |
C1—C2 | 1.389 (3) | C41—C42 | 1.524 (3) |
C1—C7 | 1.471 (3) | C23—H23 | 0.9300 |
C1—C6 | 1.388 (3) | C24—H24 | 0.9300 |
C2—C3 | 1.397 (3) | C25—H25 | 0.9300 |
C3—C4 | 1.368 (4) | C26—H26 | 0.9300 |
C4—C5 | 1.363 (4) | C27—H27 | 0.9300 |
C5—C6 | 1.385 (3) | C29—H29 | 0.9300 |
C7—C8 | 1.364 (3) | C31—H31 | 0.9300 |
C9—C10 | 1.330 (3) | C33—H33A | 0.9700 |
C9—C12 | 1.486 (2) | C33—H33B | 0.9700 |
C12—C13 | 1.517 (2) | C36—H36B | 0.9700 |
C14—C15 | 1.491 (3) | C36—H36A | 0.9700 |
C16—C17 | 1.519 (3) | C38—H38A | 0.9700 |
C16—C21 | 1.521 (3) | C38—H38B | 0.9700 |
C17—C18 | 1.522 (3) | C39—H39A | 0.9700 |
C18—C19 | 1.507 (4) | C39—H39B | 0.9700 |
C19—C20 | 1.513 (5) | C40—H40B | 0.9700 |
C20—C21 | 1.525 (3) | C40—H40A | 0.9700 |
C2—H2 | 0.9300 | C41—H41A | 0.9700 |
C3—H3 | 0.9300 | C41—H41B | 0.9700 |
C4—H4 | 0.9300 | C42—H42B | 0.9700 |
C5—H5 | 0.9300 | C42—H42A | 0.9700 |
S1···O2i | 3.3487 (17) | C6···H8 | 2.9200 |
S1···N1 | 2.5482 (15) | C8···H12B | 3.0400 |
S1···S1ii | 3.7967 (8) | C8···H17A | 3.0600 |
S1···S3ii | 3.4544 (8) | C8···H6 | 2.7600 |
S1···C10ii | 3.581 (2) | C13···H12Av | 3.0000 |
S1···C31ii | 3.608 (2) | C13···H5A | 2.906 (19) |
S2···N4 | 2.5890 (14) | C13···H17A | 2.8300 |
S2···C25iii | 3.655 (3) | C17···H41Avi | 3.0200 |
S3···C10ii | 3.685 (2) | C21···H3A | 3.0200 |
S3···O4i | 3.3109 (16) | C21···H38B | 2.9500 |
S3···N5 | 2.5507 (16) | C23···H15Aviii | 2.8600 |
S3···S1ii | 3.4544 (8) | C23···H5 | 3.1000 |
S4···C3iv | 3.610 (3) | C24···H15Aviii | 2.9000 |
S4···N8 | 2.6008 (14) | C26···H15Bviii | 3.0000 |
S4···C2iv | 3.615 (2) | C27···H29 | 2.9100 |
S1···H31ii | 3.1300 | C29···H27 | 2.7600 |
S2···H18A | 2.8700 | C29···H38A | 2.9800 |
S2···H20B | 2.8400 | C29···H33B | 3.0600 |
S3···H36Bi | 3.1600 | C32···H36Bi | 2.9400 |
S4···H41B | 2.7800 | C34···H38A | 3.0800 |
S4···H39A | 2.8700 | C34···H5Bv | 3.03 (2) |
S4···H21A | 2.8300 | C35···H5Bv | 2.934 (17) |
O1···N4 | 2.686 (2) | C39···H19Bix | 3.0500 |
O1···O2 | 3.092 (2) | C40···H19Bix | 3.0000 |
O1···C14 | 2.996 (2) | C40···H17Bvii | 3.0600 |
O1···C17 | 3.159 (2) | C41···H17Bvii | 2.8900 |
O1···O5 | 2.7097 (19) | C42···H7 | 3.1000 |
O2···N3 | 2.724 (2) | H2···N2 | 2.6200 |
O2···S1iv | 3.3487 (17) | H3A···C21 | 3.0200 |
O2···O1 | 3.092 (2) | H3A···O3 | 1.9800 |
O2···C13 | 3.082 (2) | H3A···H12B | 2.1600 |
O2···C12v | 3.074 (2) | H3A···H21B | 2.5600 |
O3···C35 | 3.122 (2) | H5···C23 | 3.1000 |
O3···N3 | 2.841 (2) | H5A···O1 | 1.880 (19) |
O3···N8 | 2.711 (2) | H5A···C13 | 2.906 (19) |
O3···O4 | 3.215 (2) | H5A···H7vi | 2.5400 |
O4···C10v | 3.306 (2) | H5B···C34v | 3.03 (2) |
O4···O5v | 2.764 (2) | H5B···C35v | 2.934 (17) |
O4···N7 | 2.713 (2) | H5B···H7vi | 2.4600 |
O4···C34 | 3.121 (2) | H5B···H33Bvi | 2.3900 |
O4···S3iv | 3.3109 (16) | H5B···O4v | 1.917 (18) |
O4···O3 | 3.215 (2) | H6···C8 | 2.7600 |
O5···C34v | 3.331 (2) | H6···H8 | 2.4000 |
O5···C33vi | 3.376 (2) | H7···H5Bvii | 2.4600 |
O5···N7vi | 2.7617 (19) | H7···H5Avii | 2.5400 |
O5···C33v | 3.349 (2) | H7···C42 | 3.1000 |
O5···O1 | 2.7097 (19) | H7···O5vii | 1.9400 |
O5···O4v | 2.764 (2) | H7···H33B | 2.1700 |
O1···H17A | 2.8600 | H8···H6 | 2.4000 |
O1···H5A | 1.880 (19) | H8···O3 | 2.8300 |
O1···H17B | 2.7900 | H8···C6 | 2.9200 |
O2···H12Av | 2.4800 | H10···O4v | 2.4100 |
O3···H8 | 2.8300 | H10···H12A | 2.5900 |
O3···H3A | 1.9800 | H12A···H10 | 2.5900 |
O3···H12B | 2.6200 | H12A···C13v | 3.0000 |
O4···H10v | 2.4100 | H12A···O2v | 2.4800 |
O4···H5Bv | 1.917 (18) | H12B···O3 | 2.6200 |
O5···H33Bvi | 2.5400 | H12B···C8 | 3.0400 |
O5···H42Avi | 2.8300 | H12B···H3A | 2.1600 |
O5···H29vi | 2.9200 | H15A···C24iii | 2.9000 |
O5···H33Av | 2.7500 | H15A···C23iii | 2.8600 |
O5···H7vi | 1.9400 | H15B···C26iii | 3.0000 |
N1···S1 | 2.5482 (15) | H15B···N2iv | 2.5700 |
N1···N2 | 2.237 (2) | H17A···H21B | 2.5500 |
N2···N1 | 2.237 (2) | H17A···C13 | 2.8300 |
N3···O2 | 2.724 (2) | H17A···O1 | 2.8600 |
N3···O3 | 2.841 (2) | H17A···N3 | 2.7100 |
N4···S2 | 2.5890 (14) | H17A···C8 | 3.0600 |
N4···O1 | 2.686 (2) | H17B···C40vi | 3.0600 |
N5···N6 | 2.237 (2) | H17B···C41vi | 2.8900 |
N5···S3 | 2.5507 (16) | H17B···H40Bvi | 2.5500 |
N6···C36i | 3.448 (3) | H17B···O1 | 2.7900 |
N6···N5 | 2.237 (2) | H17B···H41Avi | 2.2000 |
N7···O4 | 2.713 (2) | H18A···S2 | 2.8700 |
N7···O5vii | 2.7617 (19) | H19B···C39ix | 3.0500 |
N8···S4 | 2.6008 (14) | H19B···H39Bix | 2.4700 |
N8···O3 | 2.711 (2) | H19B···H40Aix | 2.4500 |
N2···H36Ai | 2.8400 | H19B···C40ix | 3.0000 |
N2···H15Bi | 2.5700 | H20B···S2 | 2.8400 |
N2···H2 | 2.6200 | H21A···S4 | 2.8300 |
N3···H17A | 2.7100 | H21B···N3 | 2.7300 |
N3···H21B | 2.7300 | H21B···H17A | 2.5500 |
N6···H36Bi | 2.5600 | H21B···H38B | 2.5200 |
N6···H23 | 2.6400 | H21B···H3A | 2.5600 |
N7···H42A | 2.9000 | H23···N6 | 2.6400 |
N7···H38A | 2.6400 | H27···C29 | 2.7600 |
C1···C36i | 3.521 (3) | H27···H29 | 2.4000 |
C2···S4i | 3.615 (2) | H29···C27 | 2.9100 |
C2···C36i | 3.519 (3) | H29···H27 | 2.4000 |
C3···S4i | 3.610 (3) | H29···H38A | 2.4400 |
C5···C23 | 3.417 (3) | H29···O5vii | 2.9200 |
C8···C13 | 3.508 (2) | H31···S1ii | 3.1300 |
C10···S1ii | 3.581 (2) | H31···H33A | 2.5900 |
C10···O4v | 3.306 (2) | H33A···H31 | 2.5900 |
C10···S3ii | 3.685 (2) | H33A···O5v | 2.7500 |
C12···O2v | 3.074 (2) | H33B···O5vii | 2.5400 |
C13···C8 | 3.508 (2) | H33B···C29 | 3.0600 |
C13···C17 | 3.306 (2) | H33B···H5Bvii | 2.3900 |
C13···O2 | 3.082 (2) | H33B···H7 | 2.1700 |
C14···O1 | 2.996 (2) | H36A···N2iv | 2.8400 |
C15···C24iii | 3.488 (3) | H36B···C1iv | 3.0600 |
C15···C25iii | 3.465 (4) | H36B···S3iv | 3.1600 |
C17···C13 | 3.306 (2) | H36B···N6iv | 2.5600 |
C17···O1 | 3.159 (2) | H36B···C32iv | 2.9400 |
C23···C5 | 3.417 (3) | H38A···N7 | 2.6400 |
C24···C15viii | 3.488 (3) | H38A···C29 | 2.9800 |
C25···C15viii | 3.465 (4) | H38A···H29 | 2.4400 |
C25···S2viii | 3.655 (3) | H38A···C34 | 3.0800 |
C29···C34 | 3.458 (3) | H38B···C21 | 2.9500 |
C31···S1ii | 3.608 (2) | H38B···H21B | 2.5200 |
C33···O5vii | 3.376 (2) | H39A···C4ix | 2.8200 |
C33···O5v | 3.349 (2) | H39A···S4 | 2.8700 |
C34···C38 | 3.457 (2) | H39B···H19Bix | 2.4700 |
C34···O5v | 3.331 (2) | H40A···H19Bix | 2.4500 |
C34···O4 | 3.121 (2) | H40B···H17Bvii | 2.5500 |
C34···C29 | 3.458 (3) | H40B···H42A | 2.5900 |
C35···O3 | 3.122 (2) | H41A···C17vii | 3.0200 |
C36···C1iv | 3.521 (3) | H41A···H17Bvii | 2.2000 |
C36···C2iv | 3.519 (3) | H41B···S4 | 2.7800 |
C36···N6iv | 3.448 (3) | H42A···N7 | 2.9000 |
C38···C34 | 3.457 (2) | H42A···H40B | 2.5900 |
C1···H36Bi | 3.0600 | H42A···O5vii | 2.8300 |
C4···H39Aix | 2.8200 | ||
C10—S1—C11 | 89.76 (9) | C18—C19—H19B | 109.00 |
C15—S2—C16 | 94.55 (9) | C18—C19—H19A | 109.00 |
C31—S3—C32 | 89.81 (10) | H20A—C20—H20B | 108.00 |
C36—S4—C37 | 93.69 (8) | C19—C20—H20A | 109.00 |
H5A—O5—H5B | 110 (2) | C21—C20—H20B | 109.00 |
C9—N1—C11 | 115.26 (14) | C21—C20—H20A | 109.00 |
C8—N1—C11 | 106.06 (14) | C19—C20—H20B | 109.00 |
C8—N1—C9 | 138.60 (15) | H21A—C21—H21B | 108.00 |
C7—N2—C11 | 103.65 (16) | C16—C21—H21A | 109.00 |
N4—N3—C13 | 120.15 (14) | C16—C21—H21B | 109.00 |
C14—N4—C16 | 121.05 (14) | C20—C21—H21B | 109.00 |
N3—N4—C16 | 118.40 (13) | C20—C21—H21A | 109.00 |
N3—N4—C14 | 118.31 (13) | C27—C22—C28 | 121.11 (19) |
C13—N3—H3A | 120.00 | C23—C22—C28 | 120.73 (19) |
N4—N3—H3A | 120.00 | C23—C22—C27 | 118.1 (2) |
C29—N5—C30 | 138.38 (16) | C22—C23—C24 | 121.0 (2) |
C30—N5—C32 | 115.52 (15) | C23—C24—C25 | 120.4 (2) |
C29—N5—C32 | 106.09 (15) | C24—C25—C26 | 120.1 (3) |
C28—N6—C32 | 103.80 (16) | C25—C26—C27 | 119.9 (2) |
N8—N7—C34 | 119.88 (13) | C22—C27—C26 | 120.6 (2) |
N7—N8—C37 | 120.22 (13) | C22—C28—C29 | 126.78 (18) |
N7—N8—C35 | 119.23 (13) | N6—C28—C29 | 111.15 (17) |
C35—N8—C37 | 120.50 (14) | N6—C28—C22 | 121.99 (18) |
N8—N7—H7 | 120.00 | N5—C29—C28 | 105.34 (16) |
C34—N7—H7 | 120.00 | N5—C30—C33 | 119.68 (16) |
C2—C1—C7 | 120.74 (18) | C31—C30—C33 | 129.22 (18) |
C6—C1—C7 | 120.96 (18) | N5—C30—C31 | 111.08 (17) |
C2—C1—C6 | 118.30 (18) | S3—C31—C30 | 113.62 (15) |
C1—C2—C3 | 120.0 (2) | N5—C32—N6 | 113.62 (17) |
C2—C3—C4 | 120.7 (2) | S3—C32—N5 | 109.94 (14) |
C3—C4—C5 | 119.7 (2) | S3—C32—N6 | 136.44 (15) |
C4—C5—C6 | 120.6 (2) | C30—C33—C34 | 111.58 (15) |
C1—C6—C5 | 120.8 (2) | N7—C34—C33 | 114.61 (15) |
N2—C7—C1 | 121.12 (16) | O3—C34—C33 | 121.81 (16) |
C1—C7—C8 | 127.44 (17) | O3—C34—N7 | 123.55 (16) |
N2—C7—C8 | 111.42 (15) | N8—C35—C36 | 111.73 (15) |
N1—C8—C7 | 105.50 (15) | O4—C35—N8 | 124.10 (17) |
C10—C9—C12 | 129.00 (17) | O4—C35—C36 | 124.17 (17) |
N1—C9—C12 | 120.05 (15) | S4—C36—C35 | 108.23 (13) |
N1—C9—C10 | 110.83 (16) | N8—C37—C38 | 111.38 (14) |
S1—C10—C9 | 113.87 (15) | S4—C37—C38 | 110.84 (12) |
S1—C11—N2 | 136.35 (16) | S4—C37—C42 | 109.67 (12) |
S1—C11—N1 | 110.25 (13) | S4—C37—N8 | 102.87 (11) |
N1—C11—N2 | 113.38 (16) | N8—C37—C42 | 110.98 (13) |
C9—C12—C13 | 109.81 (14) | C38—C37—C42 | 110.85 (14) |
O1—C13—N3 | 121.85 (16) | C37—C38—C39 | 111.58 (16) |
N3—C13—C12 | 114.82 (15) | C38—C39—C40 | 111.30 (18) |
O1—C13—C12 | 123.31 (16) | C39—C40—C41 | 111.23 (19) |
O2—C14—N4 | 124.47 (18) | C40—C41—C42 | 111.33 (18) |
N4—C14—C15 | 110.82 (16) | C37—C42—C41 | 110.31 (15) |
O2—C14—C15 | 124.72 (19) | C24—C23—H23 | 120.00 |
S2—C15—C14 | 108.78 (15) | C22—C23—H23 | 119.00 |
C17—C16—C21 | 109.66 (15) | C23—C24—H24 | 120.00 |
N4—C16—C17 | 112.39 (14) | C25—C24—H24 | 120.00 |
N4—C16—C21 | 110.48 (14) | C26—C25—H25 | 120.00 |
S2—C16—C17 | 111.81 (12) | C24—C25—H25 | 120.00 |
S2—C16—N4 | 102.18 (11) | C25—C26—H26 | 120.00 |
S2—C16—C21 | 110.13 (13) | C27—C26—H26 | 120.00 |
C16—C17—C18 | 111.68 (16) | C26—C27—H27 | 120.00 |
C17—C18—C19 | 111.47 (19) | C22—C27—H27 | 120.00 |
C18—C19—C20 | 111.3 (2) | N5—C29—H29 | 127.00 |
C19—C20—C21 | 111.4 (2) | C28—C29—H29 | 127.00 |
C16—C21—C20 | 111.24 (17) | C30—C31—H31 | 123.00 |
C1—C2—H2 | 120.00 | S3—C31—H31 | 123.00 |
C3—C2—H2 | 120.00 | C30—C33—H33A | 109.00 |
C4—C3—H3 | 120.00 | C34—C33—H33A | 109.00 |
C2—C3—H3 | 120.00 | C34—C33—H33B | 109.00 |
C3—C4—H4 | 120.00 | C30—C33—H33B | 109.00 |
C5—C4—H4 | 120.00 | H33A—C33—H33B | 108.00 |
C6—C5—H5 | 120.00 | S4—C36—H36B | 110.00 |
C4—C5—H5 | 120.00 | C35—C36—H36A | 110.00 |
C5—C6—H6 | 120.00 | C35—C36—H36B | 110.00 |
C1—C6—H6 | 120.00 | H36A—C36—H36B | 108.00 |
N1—C8—H8 | 127.00 | S4—C36—H36A | 110.00 |
C7—C8—H8 | 127.00 | C37—C38—H38B | 109.00 |
C9—C10—H10 | 123.00 | C39—C38—H38A | 109.00 |
S1—C10—H10 | 123.00 | C37—C38—H38A | 109.00 |
C13—C12—H12B | 110.00 | H38A—C38—H38B | 108.00 |
C9—C12—H12B | 110.00 | C39—C38—H38B | 109.00 |
H12A—C12—H12B | 108.00 | C38—C39—H39A | 109.00 |
C13—C12—H12A | 110.00 | C38—C39—H39B | 109.00 |
C9—C12—H12A | 110.00 | C40—C39—H39B | 109.00 |
S2—C15—H15B | 110.00 | H39A—C39—H39B | 108.00 |
C14—C15—H15A | 110.00 | C40—C39—H39A | 109.00 |
C14—C15—H15B | 110.00 | C39—C40—H40B | 109.00 |
H15A—C15—H15B | 108.00 | C41—C40—H40A | 109.00 |
S2—C15—H15A | 110.00 | C41—C40—H40B | 109.00 |
C18—C17—H17B | 109.00 | H40A—C40—H40B | 108.00 |
C16—C17—H17B | 109.00 | C39—C40—H40A | 109.00 |
H17A—C17—H17B | 108.00 | C40—C41—H41B | 109.00 |
C18—C17—H17A | 109.00 | C42—C41—H41A | 109.00 |
C16—C17—H17A | 109.00 | C40—C41—H41A | 109.00 |
C19—C18—H18A | 109.00 | H41A—C41—H41B | 108.00 |
C17—C18—H18B | 109.00 | C42—C41—H41B | 109.00 |
C17—C18—H18A | 109.00 | C37—C42—H42A | 110.00 |
C19—C18—H18B | 109.00 | C37—C42—H42B | 110.00 |
H18A—C18—H18B | 108.00 | C41—C42—H42B | 110.00 |
C20—C19—H19A | 109.00 | H42A—C42—H42B | 108.00 |
C20—C19—H19B | 109.00 | C41—C42—H42A | 110.00 |
H19A—C19—H19B | 108.00 | ||
C10—S1—C11—N2 | 176.9 (2) | C37—N8—C35—O4 | 174.60 (17) |
C10—S1—C11—N1 | −1.42 (14) | C37—N8—C35—C36 | −5.0 (2) |
C11—S1—C10—C9 | 0.62 (16) | N7—N8—C37—S4 | −167.85 (11) |
C15—S2—C16—N4 | 14.50 (13) | C6—C1—C7—N2 | 163.05 (18) |
C16—S2—C15—C14 | −11.71 (16) | C2—C1—C7—C8 | 160.2 (2) |
C15—S2—C16—C17 | −105.91 (14) | C2—C1—C7—N2 | −17.7 (3) |
C15—S2—C16—C21 | 131.92 (14) | C7—C1—C6—C5 | 178.9 (2) |
C31—S3—C32—N6 | 178.7 (2) | C6—C1—C2—C3 | 0.0 (3) |
C32—S3—C31—C30 | 0.70 (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—C35 | 14.05 (14) | C6—C1—C7—C8 | −19.0 (3) |
C36—S4—C37—C42 | 102.61 (13) | C1—C2—C3—C4 | 0.4 (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—C6 | 0.0 (4) |
C9—N1—C11—N2 | −176.73 (15) | C4—C5—C6—C1 | 0.3 (4) |
C8—N1—C11—S1 | 179.35 (12) | N2—C7—C8—N1 | 0.7 (2) |
C11—N1—C9—C12 | 174.83 (15) | C1—C7—C8—N1 | −177.46 (17) |
C11—N1—C8—C7 | −0.77 (18) | C10—C9—C12—C13 | 103.4 (2) |
C8—N1—C9—C10 | −177.71 (19) | C12—C9—C10—S1 | −175.59 (15) |
C9—N1—C11—S1 | 1.97 (19) | N1—C9—C12—C13 | −72.2 (2) |
C8—N1—C9—C12 | −1.4 (3) | N1—C9—C10—S1 | 0.4 (2) |
C8—N1—C11—N2 | 0.7 (2) | C9—C12—C13—N3 | 117.53 (17) |
C11—N1—C9—C10 | −1.5 (2) | C9—C12—C13—O1 | −61.1 (2) |
C9—N1—C8—C7 | 175.65 (18) | N4—C14—C15—S2 | 4.7 (2) |
C11—N2—C7—C1 | 177.98 (17) | O2—C14—C15—S2 | −175.19 (19) |
C11—N2—C7—C8 | −0.3 (2) | N4—C16—C21—C20 | 179.11 (19) |
C7—N2—C11—N1 | −0.2 (2) | N4—C16—C17—C18 | 179.80 (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—C20 | 67.0 (2) |
N4—N3—C13—C12 | 179.16 (14) | S2—C16—C17—C18 | −65.96 (18) |
C13—N3—N4—C16 | 96.51 (18) | C21—C16—C17—C18 | 56.5 (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—C20 | 54.4 (3) |
N3—N4—C14—C15 | 170.62 (16) | C18—C19—C20—C21 | −54.6 (3) |
N3—N4—C16—C17 | −58.36 (19) | C19—C20—C21—C16 | 56.1 (3) |
C14—N4—C16—C21 | −132.82 (18) | C23—C22—C28—C29 | 157.0 (2) |
C14—N4—C16—C17 | 104.34 (19) | C27—C22—C28—C29 | −20.6 (3) |
C14—N4—C16—S2 | −15.66 (19) | C27—C22—C28—N6 | 163.0 (2) |
N3—N4—C14—O2 | −9.5 (3) | C27—C22—C23—C24 | 0.4 (3) |
N3—N4—C16—C21 | 64.5 (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—C15 | 7.9 (2) | C28—C22—C27—C26 | 177.3 (2) |
C32—N5—C30—C33 | 176.91 (16) | C28—C22—C23—C24 | −177.4 (2) |
C30—N5—C32—N6 | −178.10 (16) | C22—C23—C24—C25 | 0.2 (4) |
C29—N5—C32—S3 | −179.06 (12) | C23—C24—C25—C26 | −0.7 (4) |
C30—N5—C32—S3 | 2.0 (2) | C24—C25—C26—C27 | 0.7 (4) |
C29—N5—C32—N6 | 0.8 (2) | C25—C26—C27—C22 | −0.1 (4) |
C29—N5—C30—C33 | −1.5 (3) | N6—C28—C29—N5 | 0.7 (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—C34 | 109.4 (2) |
C30—N5—C29—C28 | 177.7 (2) | N5—C30—C31—S3 | 0.3 (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—C22 | 176.68 (18) | C30—C33—C34—N7 | 132.25 (16) |
C28—N6—C32—S3 | 179.43 (18) | C30—C33—C34—O3 | −49.7 (2) |
C32—N6—C28—C29 | −0.2 (2) | O4—C35—C36—S4 | 172.38 (16) |
N8—N7—C34—O3 | −3.4 (3) | N8—C35—C36—S4 | −8.03 (19) |
C34—N7—N8—C37 | 109.47 (17) | S4—C37—C38—C39 | −66.61 (18) |
N8—N7—C34—C33 | 174.63 (14) | N8—C37—C38—C39 | 179.50 (15) |
C34—N7—N8—C35 | −73.1 (2) | C42—C37—C38—C39 | 55.4 (2) |
N7—N8—C35—C36 | 177.60 (14) | S4—C37—C42—C41 | 66.18 (18) |
N7—N8—C35—O4 | −2.8 (3) | N8—C37—C42—C41 | 179.15 (15) |
C35—N8—C37—S4 | 14.76 (18) | C38—C37—C42—C41 | −56.5 (2) |
C35—N8—C37—C38 | 133.53 (16) | C37—C38—C39—C40 | −54.3 (2) |
N7—N8—C37—C38 | −49.08 (19) | C38—C39—C40—C41 | 54.6 (2) |
C35—N8—C37—C42 | −102.45 (18) | C39—C40—C41—C42 | −56.4 (2) |
N7—N8—C37—C42 | 74.93 (19) | C40—C41—C42—C37 | 57.3 (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3 | 0.86 | 1.98 | 2.841 (2) | 175 |
O5—H5A···O1 | 0.833 (19) | 1.880 (19) | 2.7097 (19) | 174.4 (18) |
O5—H5B···O4v | 0.848 (18) | 1.917 (18) | 2.764 (2) | 177 (2) |
N7—H7···O5vii | 0.86 | 1.94 | 2.7617 (19) | 160 |
C10—H10···O4v | 0.93 | 2.41 | 3.306 (2) | 161 |
C12—H12A···O2v | 0.97 | 2.48 | 3.074 (2) | 120 |
C15—H15B···N2iv | 0.97 | 2.57 | 3.462 (3) | 153 |
C18—H18A···S2 | 0.97 | 2.87 | 3.255 (2) | 105 |
C20—H20B···S2 | 0.97 | 2.84 | 3.227 (3) | 105 |
C21—H21A···S4 | 0.97 | 2.83 | 3.768 (2) | 163 |
C33—H33B···O5vii | 0.97 | 2.54 | 3.376 (2) | 144 |
C36—H36B···N6iv | 0.97 | 2.56 | 3.448 (3) | 153 |
C39—H39A···S4 | 0.97 | 2.87 | 3.246 (2) | 104 |
C41—H41B···S4 | 0.97 | 2.78 | 3.194 (2) | 106 |
Symmetry codes: (iv) x+1, y, z; (v) −x+1, −y, −z+2; (vii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C21H22N4O2S2·0.5H2O |
Mr | 435.58 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 11.0175 (3), 11.8817 (3), 17.6162 (5) |
α, β, γ (°) | 75.123 (2), 73.502 (2), 81.012 (2) |
V (Å3) | 2128.36 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.52 × 0.39 × 0.25 |
Data collection | |
Diffractometer | Stoe IPDS2 diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.869, 0.934 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38012, 8351, 6705 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.098, 1.02 |
No. of reflections | 8351 |
No. of parameters | 538 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.34 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3 | 0.86 | 1.98 | 2.841 (2) | 175 |
O5—H5A···O1 | 0.833 (19) | 1.880 (19) | 2.7097 (19) | 174.4 (18) |
O5—H5B···O4i | 0.848 (18) | 1.917 (18) | 2.764 (2) | 177 (2) |
N7—H7···O5ii | 0.86 | 1.94 | 2.7617 (19) | 160 |
C10—H10···O4i | 0.93 | 2.41 | 3.306 (2) | 161 |
C12—H12A···O2i | 0.97 | 2.48 | 3.074 (2) | 120 |
C15—H15B···N2iii | 0.97 | 2.57 | 3.462 (3) | 153 |
C18—H18A···S2 | 0.97 | 2.87 | 3.255 (2) | 105 |
C20—H20B···S2 | 0.97 | 2.84 | 3.227 (3) | 105 |
C21—H21A···S4 | 0.97 | 2.83 | 3.768 (2) | 163 |
C33—H33B···O5ii | 0.97 | 2.54 | 3.376 (2) | 144 |
C36—H36B···N6iii | 0.97 | 2.56 | 3.448 (3) | 153 |
C39—H39A···S4 | 0.97 | 2.87 | 3.246 (2) | 104 |
C41—H41B···S4 | 0.97 | 2.78 | 3.194 (2) | 106 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x, y+1, z; (iii) x+1, y, z. |
Acknowledgements
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).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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-\<i>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, ϕ(2) = 342.0 (6) ° for molecule A, and Q(2) = 0.193 (2) Å, ϕ(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) °, ϕ = 179 (7) ° for molecule A, and QT = 0.570 (2) Å, θ =179.6 (2) °, ϕ = 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).