Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031650/hb2465sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031650/hb2465Isup2.hkl |
CCDC reference: 657667
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.056
- wR factor = 0.174
- Data-to-parameter ratio = 23.9
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Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
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For related literature, see: Allen et al. (1987); Andres et al. (2000); Ateş et al. (1997); Çapan et al. (1999); Cremer & Pople (1975); Güzel et al. (2006); Karalı, Terzioğlu & Gürsoy (1998); Srivastava et al. (2005); Ulusoy (2002); Ulusoy et al. (1997).
A mixture of 2-hydroxy-2,2-diphenylacetohydrazide (0.005 mol), cyclohexanone (0.005 mol) and mercaptoacetic acid or α-mercaptopropionic acid (0.02 mol) was refluxed in 20 ml dry benzene for 5–6 h using a Dean-Stark water separator. Excess benzene was evaporated in vacuo. The resulting residue was titrated with saturated NaHCO3 solution until CO2 evolution ceased and was allowed to stand overnight or in some cases refrigerated until solidification. The solid thus obtained was recrystallized from ethanol.
Yield 47%; mp 493–495 K; IR(KBr) (ν, cm-1): 3354 (O—H/N—H), 1685, 1726 (C═O). 1H-NMR (DMSO-d6, 500 MHz) δ (p.p.m.): 0.80–1.07 (m, 1H, spirodecane), 1.34–1.38 (m, 2H, spirodecane), 1.49–1.63 (m, 5H, spirodecane), 1.73, 1.76 (2 s, 2H, spirodecane), 3.54 (s, 2H, C2—H2), 6.81 (s, 1H, COH), 7.28–7.35 (m, 6H, Ar—H), 7.46 (s, 2H, Ar—H), 7.47–7.48 (m, 2H, Ar—H), 10.21 (s, 1H, CONH). 13C-NMR (APT) (DMSO-d6 / 125 MHz) δ (p.p.m.): 23.56 (C7,9 spd.), 24.83 (C8 spd.), 28.64 (C2 spd.), 37.61 (C6,10 spd.), 73.30 (C5 spd.), 81.61 (C—OH), 128.05,128.25,128.30 (ar. CH), 144.40 (ar. C), 167.98 (amide C═O), 173.40 (lactam C═O). Analysis calculated for C22H24N2O3S (396.494): C 66.64, H 6.10, N 7.07%. Found: C 66.21, H 6.22, N 6.69%.
The NH H atom were found from a difference Fourier map and refined freely. The other H atoms were positioned geometrically, with C—H = 0.93–0.97Å and O—H = 0.82 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
4-Thiazolidinones and their spiroheterocyclic analogs have been shown to possess antibacterial (Ateş et al., 1997; Andres et al., 2000), antifungal (Ulusoy et al., 1997; Çapan et al., 1999) and antituberculosis (Ulusoy, 2002; Karalı et al., 1998; Srivastava et al., 2005) activities. In our previous report (Güzel et al., 2006), we have synthesized and evaluated sixteen new 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-αzaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide derivatives, incorporating the thiazolidinone substructure, as potential antimycobacterials. We now report the crystal structure of the title compound, (I), (Fig. 1), which has a non-planar conformation.
All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The dihedral angle between the two phenyl rings is 70.28 (11)°. The five-membered ring (S1/N2/C15—C17) is not planar, with puckering parameters (Cremer & Pople, 1975) Q2 = 0.2791 (18) Å and φ2 = 171.1 (4) °. The C17—C22 cyclohexane ring has a normal chair conformation [puckering parameters: Q = 0.559 (2) Å, θ = 180.00 (2)° and φ = 341 (9) °].
The molecular conformation and crystal packing (Fig. 2) is stabilized by intramolecular N—H···O and intermolecular C—H···O and O—H···O hydrogen bonds (Table 1). The packing of (I) also features a C–H···π interaction, viz: C10—H10···Cg2(1 - x, -y, 1 - z), where Cg denotes the centre of the C1—C6 phenyl ring [C···Cg = 3.721 (3) Å, H···Cg = 2.82 Å and C–H···Cg = 162 °].
For related literature, see: Allen et al. (1987); Andres et al. (2000); Ateş et al. (1997); Çapan et al. (1999); Cremer & Pople (1975); Güzel et al. (2006); Karalı, Terzioğlu & Gürsoy (1998); Srivastava et al. (2005); Ulusoy (2002); Ulusoy et al. (1997).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C22H24N2O3S | F(000) = 840 |
Mr = 396.50 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 9135 reflections |
a = 12.1676 (2) Å | θ = 2.1–30.5° |
b = 9.3050 (2) Å | µ = 0.19 mm−1 |
c = 17.9081 (3) Å | T = 294 K |
β = 95.4236 (11)° | Prism, pale yellow |
V = 2018.47 (6) Å3 | 0.20 × 0.20 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID-S diffractometer | 6181 independent reflections |
Radiation source: Sealed Tube | 3693 reflections with I > 2σ(I) |
Graphite Monochromator monochromator | Rint = 0.067 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 30.7°, θmin = 2.3° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −13→11 |
Tmin = 0.963, Tmax = 0.963 | l = −25→25 |
56688 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.174 | w = 1/[σ2(Fo2) + (0.0679P)2 + 0.3246P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
6181 reflections | Δρmax = 0.28 e Å−3 |
259 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/sin(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0127 (15) |
C22H24N2O3S | V = 2018.47 (6) Å3 |
Mr = 396.50 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1676 (2) Å | µ = 0.19 mm−1 |
b = 9.3050 (2) Å | T = 294 K |
c = 17.9081 (3) Å | 0.20 × 0.20 × 0.20 mm |
β = 95.4236 (11)° |
Rigaku R-AXIS RAPID-S diffractometer | 6181 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 3693 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.963 | Rint = 0.067 |
56688 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.174 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.28 e Å−3 |
6181 reflections | Δρmin = −0.32 e Å−3 |
259 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 | 0.80752 (5) | 0.06874 (7) | 0.00974 (3) | 0.0757 (2) | |
O1 | 0.60444 (10) | 0.26567 (12) | 0.31383 (7) | 0.0493 (4) | |
O2 | 0.57202 (11) | −0.04849 (13) | 0.19848 (7) | 0.0564 (4) | |
O3 | 0.52028 (12) | 0.17812 (18) | 0.06223 (9) | 0.0772 (6) | |
N1 | 0.66222 (13) | 0.16220 (17) | 0.18918 (8) | 0.0494 (5) | |
N2 | 0.69225 (12) | 0.13232 (16) | 0.11812 (8) | 0.0484 (4) | |
C1 | 0.77259 (16) | 0.1061 (2) | 0.37823 (12) | 0.0636 (7) | |
C2 | 0.85941 (19) | 0.0326 (3) | 0.41713 (15) | 0.0809 (9) | |
C3 | 0.85038 (19) | −0.1121 (3) | 0.43089 (13) | 0.0778 (9) | |
C4 | 0.7553 (2) | −0.1830 (2) | 0.40626 (13) | 0.0738 (8) | |
C5 | 0.66836 (16) | −0.1106 (2) | 0.36760 (11) | 0.0592 (7) | |
C6 | 0.67673 (14) | 0.03552 (18) | 0.35312 (9) | 0.0470 (5) | |
C7 | 0.58364 (13) | 0.11450 (17) | 0.30554 (9) | 0.0440 (5) | |
C8 | 0.46878 (13) | 0.07835 (18) | 0.32601 (10) | 0.0459 (5) | |
C9 | 0.44939 (17) | 0.0643 (3) | 0.40028 (12) | 0.0698 (8) | |
C10 | 0.3446 (2) | 0.0374 (3) | 0.42036 (15) | 0.0837 (10) | |
C11 | 0.25785 (18) | 0.0262 (2) | 0.36688 (17) | 0.0777 (9) | |
C12 | 0.27456 (17) | 0.0434 (2) | 0.29364 (16) | 0.0754 (9) | |
C13 | 0.38002 (16) | 0.0703 (2) | 0.27252 (12) | 0.0582 (6) | |
C14 | 0.60133 (14) | 0.06778 (18) | 0.22493 (9) | 0.0457 (5) | |
C15 | 0.61414 (16) | 0.1364 (2) | 0.05903 (11) | 0.0568 (6) | |
C16 | 0.6604 (2) | 0.0817 (3) | −0.01015 (12) | 0.0760 (9) | |
C17 | 0.80025 (14) | 0.06507 (18) | 0.11158 (10) | 0.0490 (5) | |
C18 | 0.89297 (16) | 0.1561 (2) | 0.15033 (12) | 0.0604 (7) | |
C19 | 1.00600 (17) | 0.0872 (2) | 0.14582 (15) | 0.0733 (8) | |
C20 | 1.00933 (19) | −0.0637 (3) | 0.17748 (17) | 0.0821 (9) | |
C21 | 0.91890 (18) | −0.1551 (2) | 0.13800 (16) | 0.0771 (9) | |
C22 | 0.80573 (16) | −0.0880 (2) | 0.14201 (13) | 0.0617 (7) | |
H1 | 0.77930 | 0.20390 | 0.36900 | 0.0760* | |
H1N | 0.6718 (17) | 0.247 (2) | 0.2053 (11) | 0.063 (6)* | |
H1O | 0.54590 | 0.30960 | 0.30790 | 0.0740* | |
H2 | 0.92380 | 0.08140 | 0.43390 | 0.0970* | |
H3 | 0.90850 | −0.16150 | 0.45680 | 0.0930* | |
H4 | 0.74910 | −0.28090 | 0.41560 | 0.0890* | |
H5 | 0.60410 | −0.15990 | 0.35130 | 0.0710* | |
H9 | 0.50780 | 0.07310 | 0.43740 | 0.0840* | |
H10 | 0.33320 | 0.02680 | 0.47070 | 0.1000* | |
H11 | 0.18750 | 0.00690 | 0.38050 | 0.0930* | |
H12 | 0.21510 | 0.03720 | 0.25710 | 0.0910* | |
H13 | 0.39040 | 0.08290 | 0.22210 | 0.0700* | |
H16A | 0.64230 | 0.14710 | −0.05170 | 0.0910* | |
H16B | 0.62950 | −0.01190 | −0.02370 | 0.0910* | |
H18A | 0.88030 | 0.16900 | 0.20260 | 0.0730* | |
H18B | 0.89220 | 0.25030 | 0.12700 | 0.0730* | |
H19A | 1.02250 | 0.08430 | 0.09390 | 0.0880* | |
H19B | 1.06200 | 0.14530 | 0.17360 | 0.0880* | |
H20A | 1.08050 | −0.10680 | 0.17140 | 0.0990* | |
H20B | 1.00030 | −0.06010 | 0.23070 | 0.0990* | |
H21A | 0.92010 | −0.24960 | 0.16090 | 0.0930* | |
H21B | 0.93260 | −0.16690 | 0.08590 | 0.0930* | |
H22A | 0.78830 | −0.08730 | 0.19380 | 0.0740* | |
H22B | 0.75070 | −0.14630 | 0.11340 | 0.0740* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0720 (4) | 0.1023 (5) | 0.0557 (3) | 0.0087 (3) | 0.0218 (3) | −0.0021 (3) |
O1 | 0.0509 (6) | 0.0392 (6) | 0.0576 (7) | 0.0011 (5) | 0.0048 (5) | −0.0026 (5) |
O2 | 0.0601 (8) | 0.0494 (7) | 0.0618 (8) | −0.0122 (6) | 0.0166 (6) | −0.0119 (6) |
O3 | 0.0611 (9) | 0.0903 (12) | 0.0788 (10) | 0.0182 (8) | −0.0009 (7) | −0.0057 (8) |
N1 | 0.0578 (9) | 0.0441 (8) | 0.0484 (8) | −0.0049 (7) | 0.0164 (6) | −0.0024 (6) |
N2 | 0.0485 (8) | 0.0522 (8) | 0.0454 (7) | 0.0019 (6) | 0.0099 (6) | 0.0003 (6) |
C1 | 0.0505 (10) | 0.0599 (12) | 0.0784 (13) | −0.0005 (9) | −0.0039 (9) | 0.0031 (10) |
C2 | 0.0538 (12) | 0.0871 (17) | 0.0981 (18) | 0.0035 (11) | −0.0126 (11) | 0.0015 (13) |
C3 | 0.0653 (13) | 0.0869 (17) | 0.0797 (15) | 0.0255 (12) | −0.0016 (11) | 0.0112 (12) |
C4 | 0.0791 (15) | 0.0571 (12) | 0.0859 (16) | 0.0150 (11) | 0.0111 (12) | 0.0159 (11) |
C5 | 0.0567 (11) | 0.0512 (11) | 0.0701 (12) | 0.0022 (8) | 0.0076 (9) | 0.0082 (9) |
C6 | 0.0466 (9) | 0.0471 (9) | 0.0480 (9) | 0.0035 (7) | 0.0081 (7) | 0.0020 (7) |
C7 | 0.0457 (8) | 0.0403 (8) | 0.0465 (8) | −0.0020 (6) | 0.0070 (6) | −0.0018 (6) |
C8 | 0.0431 (8) | 0.0429 (9) | 0.0522 (9) | 0.0027 (7) | 0.0076 (7) | 0.0016 (7) |
C9 | 0.0540 (11) | 0.1019 (18) | 0.0553 (11) | 0.0109 (11) | 0.0147 (9) | 0.0111 (11) |
C10 | 0.0673 (14) | 0.1045 (19) | 0.0845 (16) | 0.0194 (13) | 0.0347 (12) | 0.0258 (14) |
C11 | 0.0544 (12) | 0.0595 (13) | 0.124 (2) | 0.0012 (10) | 0.0337 (13) | 0.0064 (13) |
C12 | 0.0468 (11) | 0.0693 (14) | 0.1084 (19) | 0.0029 (10) | −0.0022 (11) | −0.0189 (12) |
C13 | 0.0497 (10) | 0.0600 (12) | 0.0642 (11) | 0.0046 (8) | 0.0024 (8) | −0.0040 (9) |
C14 | 0.0440 (8) | 0.0449 (9) | 0.0487 (9) | −0.0017 (7) | 0.0076 (7) | 0.0002 (7) |
C15 | 0.0560 (11) | 0.0582 (11) | 0.0559 (10) | 0.0037 (9) | 0.0038 (8) | 0.0014 (8) |
C16 | 0.0789 (15) | 0.0989 (18) | 0.0498 (11) | 0.0072 (13) | 0.0047 (10) | −0.0041 (11) |
C17 | 0.0477 (9) | 0.0481 (9) | 0.0524 (9) | 0.0001 (7) | 0.0111 (7) | 0.0000 (7) |
C18 | 0.0551 (10) | 0.0511 (11) | 0.0753 (13) | −0.0055 (8) | 0.0079 (9) | −0.0041 (9) |
C19 | 0.0494 (11) | 0.0657 (13) | 0.1045 (18) | −0.0076 (9) | 0.0056 (11) | −0.0074 (12) |
C20 | 0.0539 (12) | 0.0706 (15) | 0.120 (2) | 0.0088 (10) | −0.0015 (12) | 0.0030 (13) |
C21 | 0.0608 (12) | 0.0522 (12) | 0.118 (2) | 0.0049 (10) | 0.0065 (12) | 0.0013 (12) |
C22 | 0.0532 (10) | 0.0471 (10) | 0.0852 (14) | −0.0025 (8) | 0.0086 (9) | 0.0042 (9) |
S1—C16 | 1.796 (3) | C17—C18 | 1.524 (3) |
S1—C17 | 1.8346 (19) | C18—C19 | 1.526 (3) |
O1—C7 | 1.4344 (19) | C19—C20 | 1.513 (3) |
O2—C14 | 1.221 (2) | C20—C21 | 1.512 (3) |
O3—C15 | 1.213 (2) | C21—C22 | 1.520 (3) |
O1—H1O | 0.8200 | C1—H1 | 0.9300 |
N1—N2 | 1.385 (2) | C2—H2 | 0.9300 |
N1—C14 | 1.349 (2) | C3—H3 | 0.9300 |
N2—C15 | 1.354 (2) | C4—H4 | 0.9300 |
N2—C17 | 1.470 (2) | C5—H5 | 0.9300 |
N1—H1N | 0.845 (19) | C9—H9 | 0.9300 |
C1—C6 | 1.377 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.389 (3) | C11—H11 | 0.9300 |
C2—C3 | 1.375 (4) | C12—H12 | 0.9300 |
C3—C4 | 1.368 (3) | C13—H13 | 0.9300 |
C4—C5 | 1.383 (3) | C16—H16A | 0.9700 |
C5—C6 | 1.390 (3) | C16—H16B | 0.9700 |
C6—C7 | 1.538 (2) | C18—H18A | 0.9700 |
C7—C14 | 1.542 (2) | C18—H18B | 0.9700 |
C7—C8 | 1.516 (2) | C19—H19A | 0.9700 |
C8—C13 | 1.376 (3) | C19—H19B | 0.9700 |
C8—C9 | 1.379 (3) | C20—H20A | 0.9700 |
C9—C10 | 1.380 (3) | C20—H20B | 0.9700 |
C10—C11 | 1.361 (4) | C21—H21A | 0.9700 |
C11—C12 | 1.356 (4) | C21—H21B | 0.9700 |
C12—C13 | 1.394 (3) | C22—H22A | 0.9700 |
C15—C16 | 1.498 (3) | C22—H22B | 0.9700 |
C17—C22 | 1.524 (3) | ||
C16—S1—C17 | 93.30 (9) | C6—C1—H1 | 120.00 |
C7—O1—H1O | 109.00 | C1—C2—H2 | 120.00 |
N2—N1—C14 | 120.64 (15) | C3—C2—H2 | 120.00 |
N1—N2—C15 | 119.06 (15) | C2—C3—H3 | 120.00 |
N1—N2—C17 | 118.30 (14) | C4—C3—H3 | 120.00 |
C15—N2—C17 | 121.08 (15) | C3—C4—H4 | 120.00 |
N2—N1—H1N | 117.5 (13) | C5—C4—H4 | 120.00 |
C14—N1—H1N | 120.7 (14) | C4—C5—H5 | 120.00 |
C2—C1—C6 | 120.64 (19) | C6—C5—H5 | 120.00 |
C1—C2—C3 | 120.1 (2) | C8—C9—H9 | 119.00 |
C2—C3—C4 | 119.6 (2) | C10—C9—H9 | 119.00 |
C3—C4—C5 | 120.65 (19) | C9—C10—H10 | 120.00 |
C4—C5—C6 | 120.25 (18) | C11—C10—H10 | 120.00 |
C1—C6—C5 | 118.73 (16) | C10—C11—H11 | 120.00 |
C1—C6—C7 | 120.65 (15) | C12—C11—H11 | 120.00 |
C5—C6—C7 | 120.51 (15) | C11—C12—H12 | 120.00 |
O1—C7—C6 | 107.32 (13) | C13—C12—H12 | 120.00 |
C6—C7—C14 | 102.90 (13) | C8—C13—H13 | 120.00 |
C8—C7—C14 | 112.17 (14) | C12—C13—H13 | 120.00 |
C6—C7—C8 | 114.05 (13) | S1—C16—H16A | 110.00 |
O1—C7—C8 | 110.50 (13) | S1—C16—H16B | 110.00 |
O1—C7—C14 | 109.54 (13) | C15—C16—H16A | 110.00 |
C7—C8—C9 | 120.01 (16) | C15—C16—H16B | 110.00 |
C7—C8—C13 | 121.64 (16) | H16A—C16—H16B | 108.00 |
C9—C8—C13 | 118.14 (17) | C17—C18—H18A | 109.00 |
C8—C9—C10 | 121.0 (2) | C17—C18—H18B | 109.00 |
C9—C10—C11 | 120.3 (2) | C19—C18—H18A | 109.00 |
C10—C11—C12 | 119.7 (2) | C19—C18—H18B | 109.00 |
C11—C12—C13 | 120.6 (2) | H18A—C18—H18B | 108.00 |
C8—C13—C12 | 120.2 (2) | C18—C19—H19A | 109.00 |
O2—C14—N1 | 123.12 (15) | C18—C19—H19B | 109.00 |
O2—C14—C7 | 123.48 (15) | C20—C19—H19A | 109.00 |
N1—C14—C7 | 113.09 (14) | C20—C19—H19B | 109.00 |
N2—C15—C16 | 110.24 (17) | H19A—C19—H19B | 108.00 |
O3—C15—N2 | 124.51 (18) | C19—C20—H20A | 110.00 |
O3—C15—C16 | 125.25 (19) | C19—C20—H20B | 110.00 |
S1—C16—C15 | 107.72 (15) | C21—C20—H20A | 109.00 |
S1—C17—N2 | 101.46 (11) | C21—C20—H20B | 109.00 |
S1—C17—C18 | 109.82 (13) | H20A—C20—H20B | 108.00 |
S1—C17—C22 | 111.61 (13) | C20—C21—H21A | 109.00 |
N2—C17—C18 | 110.85 (14) | C20—C21—H21B | 109.00 |
N2—C17—C22 | 112.24 (14) | C22—C21—H21A | 109.00 |
C18—C17—C22 | 110.55 (15) | C22—C21—H21B | 109.00 |
C17—C18—C19 | 111.98 (16) | H21A—C21—H21B | 108.00 |
C18—C19—C20 | 111.24 (18) | C17—C22—H22A | 109.00 |
C19—C20—C21 | 110.7 (2) | C17—C22—H22B | 109.00 |
C20—C21—C22 | 111.67 (18) | C21—C22—H22A | 109.00 |
C17—C22—C21 | 112.10 (16) | C21—C22—H22B | 109.00 |
C2—C1—H1 | 120.00 | H22A—C22—H22B | 108.00 |
C17—S1—C16—C15 | 20.49 (17) | O1—C7—C8—C9 | −80.3 (2) |
C16—S1—C17—N2 | −22.19 (14) | O1—C7—C8—C13 | 94.38 (19) |
C16—S1—C17—C18 | −139.52 (15) | C6—C7—C8—C9 | 40.7 (2) |
C16—S1—C17—C22 | 97.53 (15) | C6—C7—C8—C13 | −144.64 (16) |
C14—N1—N2—C15 | 71.8 (2) | C14—C7—C8—C9 | 157.21 (18) |
C14—N1—N2—C17 | −94.09 (19) | C14—C7—C8—C13 | −28.2 (2) |
N2—N1—C14—O2 | 1.9 (3) | O1—C7—C14—O2 | −167.35 (15) |
N2—N1—C14—C7 | 175.65 (14) | O1—C7—C14—N1 | 18.93 (19) |
N1—N2—C15—O3 | 7.5 (3) | C6—C7—C14—O2 | 78.74 (19) |
N1—N2—C15—C16 | −172.32 (17) | C6—C7—C14—N1 | −94.98 (16) |
C17—N2—C15—O3 | 172.97 (18) | C8—C7—C14—O2 | −44.3 (2) |
C17—N2—C15—C16 | −6.8 (2) | C8—C7—C14—N1 | 142.02 (15) |
N1—N2—C17—S1 | −173.39 (12) | C7—C8—C9—C10 | 177.3 (2) |
N1—N2—C17—C18 | −56.8 (2) | C13—C8—C9—C10 | 2.5 (3) |
N1—N2—C17—C22 | 67.3 (2) | C7—C8—C13—C12 | −177.01 (16) |
C15—N2—C17—S1 | 21.00 (18) | C9—C8—C13—C12 | −2.3 (3) |
C15—N2—C17—C18 | 137.58 (17) | C8—C9—C10—C11 | −0.9 (4) |
C15—N2—C17—C22 | −98.3 (2) | C9—C10—C11—C12 | −0.8 (4) |
C6—C1—C2—C3 | 0.1 (4) | C10—C11—C12—C13 | 1.0 (3) |
C2—C1—C6—C5 | 0.2 (3) | C11—C12—C13—C8 | 0.6 (3) |
C2—C1—C6—C7 | −175.90 (19) | O3—C15—C16—S1 | 168.39 (18) |
C1—C2—C3—C4 | −0.2 (4) | N2—C15—C16—S1 | −11.8 (2) |
C2—C3—C4—C5 | 0.1 (4) | S1—C17—C18—C19 | −69.89 (19) |
C3—C4—C5—C6 | 0.2 (3) | N2—C17—C18—C19 | 178.81 (16) |
C4—C5—C6—C1 | −0.3 (3) | C22—C17—C18—C19 | 53.7 (2) |
C4—C5—C6—C7 | 175.79 (18) | S1—C17—C22—C21 | 69.1 (2) |
C1—C6—C7—O1 | −16.1 (2) | N2—C17—C22—C21 | −177.74 (17) |
C1—C6—C7—C8 | −138.82 (17) | C18—C17—C22—C21 | −53.4 (2) |
C1—C6—C7—C14 | 99.44 (18) | C17—C18—C19—C20 | −55.6 (3) |
C5—C6—C7—O1 | 167.93 (15) | C18—C19—C20—C21 | 56.1 (3) |
C5—C6—C7—C8 | 45.2 (2) | C19—C20—C21—C22 | −56.0 (3) |
C5—C6—C7—C14 | −76.56 (19) | C20—C21—C22—C17 | 55.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.845 (19) | 2.19 (2) | 2.5886 (19) | 109.1 (16) |
O1—H1O···O2i | 0.82 | 1.95 | 2.7494 (18) | 167 |
C1—H1···O1 | 0.93 | 2.33 | 2.697 (2) | 103 |
C13—H13···O2 | 0.93 | 2.59 | 3.004 (2) | 107 |
C16—H16A···O1ii | 0.97 | 2.54 | 3.466 (3) | 159 |
C16—H16B···O3iii | 0.97 | 2.44 | 3.341 (3) | 154 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H24N2O3S |
Mr | 396.50 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 12.1676 (2), 9.3050 (2), 17.9081 (3) |
β (°) | 95.4236 (11) |
V (Å3) | 2018.47 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.20 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID-S |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.963, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 56688, 6181, 3693 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.717 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.174, 1.04 |
No. of reflections | 6181 |
No. of parameters | 259 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.32 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.845 (19) | 2.19 (2) | 2.5886 (19) | 109.1 (16) |
O1—H1O···O2i | 0.82 | 1.95 | 2.7494 (18) | 167 |
C1—H1···O1 | 0.93 | 2.33 | 2.697 (2) | 103 |
C13—H13···O2 | 0.93 | 2.59 | 3.004 (2) | 107 |
C16—H16A···O1ii | 0.97 | 2.54 | 3.466 (3) | 159 |
C16—H16B···O3iii | 0.97 | 2.44 | 3.341 (3) | 154 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y, −z. |
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4-Thiazolidinones and their spiroheterocyclic analogs have been shown to possess antibacterial (Ateş et al., 1997; Andres et al., 2000), antifungal (Ulusoy et al., 1997; Çapan et al., 1999) and antituberculosis (Ulusoy, 2002; Karalı et al., 1998; Srivastava et al., 2005) activities. In our previous report (Güzel et al., 2006), we have synthesized and evaluated sixteen new 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-αzaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide derivatives, incorporating the thiazolidinone substructure, as potential antimycobacterials. We now report the crystal structure of the title compound, (I), (Fig. 1), which has a non-planar conformation.
All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The dihedral angle between the two phenyl rings is 70.28 (11)°. The five-membered ring (S1/N2/C15—C17) is not planar, with puckering parameters (Cremer & Pople, 1975) Q2 = 0.2791 (18) Å and φ2 = 171.1 (4) °. The C17—C22 cyclohexane ring has a normal chair conformation [puckering parameters: Q = 0.559 (2) Å, θ = 180.00 (2)° and φ = 341 (9) °].
The molecular conformation and crystal packing (Fig. 2) is stabilized by intramolecular N—H···O and intermolecular C—H···O and O—H···O hydrogen bonds (Table 1). The packing of (I) also features a C–H···π interaction, viz: C10—H10···Cg2(1 - x, -y, 1 - z), where Cg denotes the centre of the C1—C6 phenyl ring [C···Cg = 3.721 (3) Å, H···Cg = 2.82 Å and C–H···Cg = 162 °].