Crystal structure of (5Z)-5-(2-hy­droxy­benzyl­idene)-1,3-thia­zolidine-2,4-dione

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Younes, S.H.H.; Albayati, M.R.

doi:10.1107/S2056989015021908

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o965-o966

https://doi.org/10.1107/S2056989015021908

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Crystal structure of (5Z)-5-(2-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Sabry H. H. Younes ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Ishida, Okayama University, Japan (Received 30 October 2015; accepted 17 November 2015; online 21 November 2015)

The title compound, C₁₀H₇NO₃S, crystallizes with four independent molecules in the asymmetric unit with slightly different conformations; the dihedral angles between the six- and five-membered rings are 2.6 (1), 1.09 (9), 8.6 (1) and 6.2 (1)°. In the crystal, molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming sheets lying parallel to (101).

Keywords: crystal structure; thiazolidinones; hydrogen bonding.

CCDC reference: 1437385

1. Related literature

For synthesis and biological activities of thiazolidinones, see: Singh et al. (1981 ); Bondock et al. (2007 ); Vicini et al. (2008 ); Behbehani & Ibrahim (2012 ).

2. Experimental

2.1. Crystal data

C₁₀H₇NO₃S
M_r = 221.23
Triclinic, $[P \overline 1]$
a = 7.2040 (7) Å
b = 13.6544 (14) Å
c = 18.9346 (18) Å
α = 90.226 (2)°
β = 95.531 (2)°
γ = 91.330 (2)°
V = 1853.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 150 K
0.22 × 0.11 × 0.08 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009 ) T_min = 0.93, T_max = 0.97
64240 measured reflections
9869 independent reflections
5466 reflections with I > 2σ(I)
R_int = 0.074

2.3. Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.125
S = 0.93
9869 reflections
541 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5ⁱ	0.91	1.91	2.819 (2)	175
O1—H1O⋯O12ⁱⁱ	0.84	1.91	2.744 (2)	175
N2—H2N⋯O2ⁱⁱⁱ	0.91	1.96	2.859 (2)	169
O4—H2O⋯O9^iv	0.84	1.97	2.759 (2)	156
N3—H3N⋯O11^v	0.91	1.95	2.859 (2)	177
O7—H3O⋯O6ⁱ	0.84	1.94	2.757 (2)	166
N4—H4N⋯O8^vi	0.91	1.93	2.843 (2)	176
O10—H4O⋯O3^vii	0.84	1.89	2.722 (2)	169
Symmetry codes: (i) x, y+1, z; (ii) x, y, z-1; (iii) x, y-1, z; (iv) x-1, y-1, z+1; (v) x, y+1, z-1; (vi) x, y-1, z+1; (vii) x+1, y, z.

Data collection: APEX2 (Bruker, 2015 ); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1437385

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015021908/is5432sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015021908/is5432Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015021908/is5432Isup3.cml

checkCIF report

Comment top

Thiazolidinones are an important group of heterocyclic compounds. Diverse biological activities such as bactericidal, pesticidal, fungicidal, insecticidal, anticonvulsant, tuberculostatic, antiinflammatory, antithyroidal, potentiation of pentobarbital induced sleeping time, etc., have been found to be associated with thiazolidinone derivatives (Singh et al., 1981; Bondock et al., 2007; Vicini et al., 2008; Behbehani & Ibrahim, 2012). In this context we report here the synthesis and crystal structure determination of the title compound.

The title compound crystallizes with four independent molecules in the asymmetric unit with similar but significantly different conformations (Fig. 1). This is most distinctly shown by the dihedral angles between the 6- and 5-membererd rings. For molecules 1–4, respectively, these are: 2.6 (1), 1.09 (9), 8.6 (1) and 6.2 (1)°. Intermolecular N—H···O and O—H···O hydrogen bonds (Table 1 and Fig. 2) form sheets running approximately parallel to (101) (Fig. 3).

Related literature top

For synthesis and biological activities of thiazolidinones, see: Singh et al. (1981); Bondock et al. (2007); Vicini et al. (2008); Behbehani & Ibrahim (2012).

Experimental top

The title compound was obtained as a major product from a three component reaction of 2-hydroxy-benzaldehyde (1 mmol, 122 mg), thiazolidine-2,4-dione (1 mmol, 117 mg) and 1-aminopropan-2-ol (1 mmol, 75 mg) under reflux. The reaction was monitored by TLC till completion. On cooling the solid product was collected by filteration, dried under vacuum and recrystallized from ethanol to afford yellow crystals in a sufficient quality for X-ray diffraction. M.p. 558 K.

Structure description top

For synthesis and biological activities of thiazolidinones, see: Singh et al. (1981); Bondock et al. (2007); Vicini et al. (2008); Behbehani & Ibrahim (2012).

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

Figures top

	Fig. 1. The asymmetric unit showing labeling scheme and 50% probability ellipsoids.
	Fig. 2. A packing diagram viewed down the a axis with O—H···O and N—H···N hydrogen bonds shown, respectively, as red and blue dotted lines.
	Fig. 3. A packing diagram viewed down the b axis showing the sheet structure.

(5Z)-5-(2-Hydroxybenzylidene)-1,3-thiazolidine-2,4-dione top

Crystal data top

C₁₀H₇NO₃S	Z = 8
M_r = 221.23	F(000) = 912
Triclinic, P1	D_x = 1.586 Mg m⁻³
a = 7.2040 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.6544 (14) Å	Cell parameters from 6790 reflections
c = 18.9346 (18) Å	θ = 2.6–28.4°
α = 90.226 (2)°	µ = 0.33 mm⁻¹
β = 95.531 (2)°	T = 150 K
γ = 91.330 (2)°	Parallelepiped, yellow
V = 1853.3 (3) Å³	0.22 × 0.11 × 0.08 mm

Data collection top

Bruker SMART APEX CCD diffractometer	9869 independent reflections
Radiation source: fine-focus sealed tube	5466 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.4°, θ_min = 1.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −18→18
T_min = 0.93, T_max = 0.97	l = −26→26
64240 measured reflections

Refinement top

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)] = 0.051	Hydrogen site location: mixed
wR(F²) = 0.125	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0665P)²] where P = (F_o² + 2F_c²)/3
9869 reflections	(Δ/σ)_max < 0.001
541 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₀H₇NO₃S	γ = 91.330 (2)°
M_r = 221.23	V = 1853.3 (3) Å³
Triclinic, P1	Z = 8
a = 7.2040 (7) Å	Mo Kα radiation
b = 13.6544 (14) Å	µ = 0.33 mm⁻¹
c = 18.9346 (18) Å	T = 150 K
α = 90.226 (2)°	0.22 × 0.11 × 0.08 mm
β = 95.531 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	9869 independent reflections
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	5466 reflections with I > 2σ(I)
T_min = 0.93, T_max = 0.97	R_int = 0.074
64240 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 0.93	Δρ_max = 0.53 e Å⁻³
9869 reflections	Δρ_min = −0.38 e Å⁻³
541 parameters

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 20 sec/frame. Analysis of 852 reflections having I/σ(I) > 13 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the triclinic system and to consist of one major and two minor components. The second of the minor components was considered to be small enough compared to the others that it could be neglected in the integration. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while those attached to nitrogen and oxygen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91%A and O—H = 0.84%A. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. Trial refinements after all atoms were included indicated that the single component reflection file extracted from the twinned data set gave superior results.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.40644 (8)	0.38610 (4)	0.38644 (3)	0.02299 (14)
O1	0.6291 (2)	0.42858 (11)	0.12068 (9)	0.0370 (5)
H1O	0.6690	0.4266	0.0804	0.044*
O2	0.4643 (2)	0.63917 (11)	0.30031 (8)	0.0254 (4)
O3	0.2764 (2)	0.47843 (12)	0.49334 (8)	0.0294 (4)
N1	0.3645 (2)	0.57249 (13)	0.40148 (9)	0.0219 (4)
H1N	0.3543	0.6318	0.4226	0.026*
C1	0.5409 (3)	0.34462 (16)	0.22111 (12)	0.0208 (5)
C2	0.5130 (3)	0.25416 (16)	0.25447 (12)	0.0254 (5)
H2	0.4697	0.2536	0.3003	0.031*
C3	0.5467 (3)	0.16666 (17)	0.22248 (13)	0.0294 (6)
H3	0.5272	0.1066	0.2462	0.035*
C4	0.6098 (3)	0.16625 (17)	0.15511 (12)	0.0279 (5)
H4	0.6335	0.1059	0.1329	0.033*
C5	0.6375 (3)	0.25316 (17)	0.12096 (12)	0.0271 (5)
H5	0.6813	0.2527	0.0752	0.032*
C6	0.6020 (3)	0.34172 (16)	0.15285 (12)	0.0241 (5)
C7	0.5131 (3)	0.43940 (16)	0.25299 (11)	0.0217 (5)
H7	0.5366	0.4937	0.2237	0.026*
C8	0.4605 (3)	0.46345 (15)	0.31612 (11)	0.0184 (5)
C9	0.4339 (3)	0.56730 (16)	0.33623 (11)	0.0195 (5)
C10	0.3375 (3)	0.48608 (17)	0.43577 (12)	0.0225 (5)
S2	0.32807 (8)	0.01122 (4)	0.37273 (3)	0.02336 (14)
O4	0.1704 (2)	−0.04010 (11)	0.64706 (8)	0.0285 (4)
H2O	0.1434	−0.0225	0.6873	0.034*
O5	0.3142 (2)	−0.24179 (11)	0.46129 (8)	0.0268 (4)
O6	0.4279 (2)	−0.07906 (12)	0.25874 (8)	0.0293 (4)
N2	0.3748 (2)	−0.17408 (13)	0.35499 (9)	0.0218 (4)
H2N	0.3958	−0.2309	0.3322	0.026*
C11	0.2175 (3)	0.04760 (16)	0.54267 (11)	0.0192 (5)
C12	0.1743 (3)	0.04827 (16)	0.61370 (12)	0.0202 (5)
C13	0.1370 (3)	0.13555 (16)	0.64762 (12)	0.0242 (5)
H13	0.1067	0.1347	0.6953	0.029*
C14	0.1441 (3)	0.22250 (17)	0.61207 (13)	0.0267 (5)
H14	0.1205	0.2818	0.6356	0.032*
C15	0.1853 (3)	0.22489 (17)	0.54197 (13)	0.0292 (6)
H15	0.1884	0.2854	0.5174	0.035*
C16	0.2219 (3)	0.13864 (16)	0.50825 (12)	0.0243 (5)
H16	0.2509	0.1408	0.4604	0.029*
C17	0.2538 (3)	−0.04522 (16)	0.50986 (11)	0.0190 (5)
H17	0.2452	−0.1002	0.5400	0.023*
C18	0.2977 (3)	−0.06743 (15)	0.44423 (11)	0.0188 (5)
C19	0.3286 (3)	−0.16940 (16)	0.42378 (11)	0.0202 (5)
C20	0.3851 (3)	−0.08749 (16)	0.31868 (12)	0.0217 (5)
S3	0.90516 (8)	0.88184 (4)	−0.11410 (3)	0.02609 (15)
O7	0.6217 (2)	0.92781 (11)	0.14016 (8)	0.0326 (4)
H3O	0.5773	0.9192	0.1791	0.039*
O8	0.7715 (2)	1.13295 (11)	−0.04415 (8)	0.0266 (4)
O9	1.0061 (2)	0.97420 (12)	−0.22769 (8)	0.0329 (4)
N3	0.8938 (2)	1.06761 (13)	−0.14051 (9)	0.0222 (4)
H3N	0.9001	1.1261	−0.1631	0.027*
C21	0.7074 (3)	0.84107 (16)	0.04052 (11)	0.0199 (5)
C22	0.6480 (3)	0.83940 (16)	0.10950 (12)	0.0239 (5)
C23	0.6200 (3)	0.75171 (17)	0.14383 (12)	0.0262 (5)
H23	0.5818	0.7518	0.1905	0.031*
C24	0.6476 (3)	0.66414 (17)	0.11018 (13)	0.0292 (6)
H24	0.6277	0.6042	0.1339	0.035*
C25	0.7037 (3)	0.66242 (17)	0.04226 (13)	0.0302 (6)
H25	0.7211	0.6019	0.0191	0.036*
C26	0.7342 (3)	0.75025 (17)	0.00866 (12)	0.0268 (5)
H26	0.7748	0.7490	−0.0376	0.032*
C27	0.7336 (3)	0.93551 (16)	0.00744 (11)	0.0200 (5)
H27	0.6925	0.9899	0.0327	0.024*
C28	0.8069 (3)	0.95820 (16)	−0.05322 (11)	0.0202 (5)
C29	0.8192 (3)	1.06154 (16)	−0.07655 (11)	0.0196 (5)
C30	0.9443 (3)	0.98161 (17)	−0.17070 (12)	0.0238 (5)
S4	0.87243 (9)	0.50738 (4)	0.87921 (3)	0.02846 (16)
O10	1.1108 (2)	0.46387 (11)	0.61625 (8)	0.0274 (4)
H4O	1.1551	0.4753	0.5776	0.033*
O11	0.9134 (2)	0.25436 (11)	0.79255 (8)	0.0286 (4)
O12	0.7722 (3)	0.41381 (13)	0.99199 (9)	0.0386 (5)
N4	0.8343 (2)	0.32045 (13)	0.89658 (9)	0.0237 (4)
H4N	0.8161	0.2615	0.9174	0.028*
C31	1.0119 (3)	0.54867 (16)	0.71490 (11)	0.0197 (5)
C32	1.0756 (3)	0.55082 (15)	0.64669 (11)	0.0197 (5)
C33	1.0984 (3)	0.63921 (16)	0.61191 (12)	0.0233 (5)
H33	1.1400	0.6396	0.5658	0.028*
C34	1.0609 (3)	0.72617 (17)	0.64428 (12)	0.0269 (5)
H34	1.0772	0.7864	0.6205	0.032*
C35	0.9989 (3)	0.72613 (16)	0.71194 (12)	0.0249 (5)
H35	0.9735	0.7862	0.7342	0.030*
C36	0.9750 (3)	0.63891 (16)	0.74614 (12)	0.0220 (5)
H36	0.9323	0.6395	0.7921	0.026*
C37	0.9820 (3)	0.45351 (16)	0.74680 (11)	0.0203 (5)
H37	1.0082	0.3991	0.7182	0.024*
C38	0.9236 (3)	0.42983 (16)	0.80996 (11)	0.0204 (5)
C39	0.8931 (3)	0.32598 (17)	0.82932 (12)	0.0223 (5)
C40	0.8174 (3)	0.40666 (18)	0.93258 (12)	0.0259 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0304 (3)	0.0206 (3)	0.0193 (3)	0.0001 (2)	0.0096 (2)	0.0009 (2)
O1	0.0658 (13)	0.0232 (9)	0.0265 (10)	0.0031 (8)	0.0273 (9)	0.0037 (7)
O2	0.0356 (10)	0.0195 (8)	0.0230 (9)	0.0006 (7)	0.0114 (7)	0.0011 (7)
O3	0.0359 (10)	0.0323 (9)	0.0221 (9)	−0.0022 (8)	0.0137 (7)	−0.0027 (7)
N1	0.0288 (11)	0.0153 (10)	0.0228 (11)	0.0019 (8)	0.0095 (8)	−0.0044 (8)
C1	0.0215 (12)	0.0188 (12)	0.0230 (12)	0.0014 (9)	0.0065 (9)	−0.0009 (9)
C2	0.0302 (13)	0.0224 (12)	0.0251 (13)	0.0008 (10)	0.0094 (10)	0.0022 (10)
C3	0.0354 (14)	0.0212 (13)	0.0328 (14)	−0.0007 (10)	0.0090 (11)	0.0012 (11)
C4	0.0333 (14)	0.0229 (13)	0.0280 (14)	0.0030 (10)	0.0059 (10)	−0.0052 (10)
C5	0.0323 (14)	0.0264 (13)	0.0239 (13)	0.0019 (10)	0.0099 (10)	−0.0024 (10)
C6	0.0272 (13)	0.0214 (12)	0.0251 (13)	−0.0001 (10)	0.0097 (10)	−0.0003 (10)
C7	0.0251 (12)	0.0188 (12)	0.0221 (12)	−0.0001 (9)	0.0060 (9)	0.0048 (9)
C8	0.0172 (11)	0.0182 (11)	0.0204 (12)	0.0005 (9)	0.0040 (9)	0.0016 (9)
C9	0.0191 (12)	0.0205 (12)	0.0200 (12)	0.0013 (9)	0.0068 (9)	−0.0030 (9)
C10	0.0210 (12)	0.0275 (13)	0.0197 (12)	0.0017 (10)	0.0052 (9)	−0.0020 (10)
S2	0.0310 (3)	0.0213 (3)	0.0192 (3)	0.0022 (2)	0.0094 (2)	0.0018 (2)
O4	0.0447 (10)	0.0212 (9)	0.0225 (9)	0.0020 (7)	0.0180 (7)	−0.0001 (7)
O5	0.0372 (10)	0.0206 (9)	0.0246 (9)	0.0006 (7)	0.0133 (7)	−0.0011 (7)
O6	0.0388 (10)	0.0313 (10)	0.0198 (9)	0.0010 (8)	0.0126 (7)	−0.0017 (7)
N2	0.0296 (11)	0.0193 (10)	0.0174 (10)	0.0010 (8)	0.0071 (8)	−0.0032 (8)
C11	0.0186 (11)	0.0213 (12)	0.0186 (11)	0.0004 (9)	0.0056 (9)	−0.0012 (9)
C12	0.0207 (12)	0.0178 (11)	0.0227 (12)	0.0000 (9)	0.0050 (9)	0.0000 (9)
C13	0.0250 (13)	0.0269 (13)	0.0219 (12)	0.0009 (10)	0.0088 (9)	−0.0064 (10)
C14	0.0305 (14)	0.0181 (12)	0.0330 (14)	0.0026 (10)	0.0102 (10)	−0.0070 (11)
C15	0.0348 (14)	0.0221 (13)	0.0321 (14)	0.0038 (11)	0.0102 (11)	0.0020 (11)
C16	0.0291 (13)	0.0221 (12)	0.0231 (13)	0.0033 (10)	0.0092 (10)	0.0013 (10)
C17	0.0198 (11)	0.0191 (11)	0.0188 (11)	−0.0003 (9)	0.0051 (9)	0.0012 (9)
C18	0.0185 (11)	0.0189 (11)	0.0199 (12)	0.0003 (9)	0.0064 (9)	0.0011 (9)
C19	0.0184 (11)	0.0213 (12)	0.0217 (12)	−0.0002 (9)	0.0055 (9)	−0.0004 (10)
C20	0.0218 (12)	0.0227 (12)	0.0212 (12)	0.0007 (9)	0.0052 (9)	0.0004 (10)
S3	0.0365 (4)	0.0219 (3)	0.0220 (3)	0.0032 (3)	0.0137 (3)	−0.0002 (2)
O7	0.0552 (12)	0.0220 (9)	0.0238 (9)	−0.0029 (8)	0.0209 (8)	−0.0031 (7)
O8	0.0334 (9)	0.0227 (9)	0.0255 (9)	0.0038 (7)	0.0118 (7)	0.0005 (7)
O9	0.0461 (11)	0.0348 (10)	0.0206 (9)	0.0025 (8)	0.0174 (8)	0.0000 (8)
N3	0.0301 (11)	0.0182 (10)	0.0197 (10)	0.0015 (8)	0.0088 (8)	0.0029 (8)
C21	0.0199 (11)	0.0207 (12)	0.0200 (12)	−0.0004 (9)	0.0060 (9)	0.0015 (9)
C22	0.0271 (13)	0.0201 (12)	0.0252 (13)	−0.0013 (10)	0.0076 (10)	−0.0019 (10)
C23	0.0316 (14)	0.0275 (13)	0.0208 (12)	−0.0018 (10)	0.0095 (10)	0.0044 (10)
C24	0.0314 (14)	0.0213 (13)	0.0360 (15)	−0.0019 (10)	0.0093 (11)	0.0085 (11)
C25	0.0369 (15)	0.0181 (12)	0.0374 (15)	0.0009 (10)	0.0129 (11)	0.0002 (11)
C26	0.0317 (14)	0.0252 (13)	0.0249 (13)	0.0012 (10)	0.0100 (10)	0.0001 (10)
C27	0.0234 (12)	0.0175 (11)	0.0199 (12)	−0.0009 (9)	0.0063 (9)	−0.0010 (9)
C28	0.0193 (12)	0.0237 (12)	0.0181 (12)	0.0017 (9)	0.0045 (9)	−0.0001 (9)
C29	0.0177 (11)	0.0223 (12)	0.0195 (12)	0.0009 (9)	0.0044 (9)	0.0015 (10)
C30	0.0275 (13)	0.0257 (13)	0.0192 (12)	−0.0007 (10)	0.0069 (9)	0.0016 (10)
S4	0.0442 (4)	0.0226 (3)	0.0206 (3)	−0.0011 (3)	0.0146 (3)	−0.0020 (2)
O10	0.0387 (10)	0.0227 (9)	0.0236 (9)	0.0050 (7)	0.0162 (7)	0.0006 (7)
O11	0.0428 (10)	0.0209 (9)	0.0240 (9)	0.0017 (7)	0.0135 (7)	0.0009 (7)
O12	0.0602 (13)	0.0379 (11)	0.0212 (9)	−0.0016 (9)	0.0220 (8)	−0.0018 (8)
N4	0.0326 (11)	0.0188 (10)	0.0208 (10)	−0.0032 (8)	0.0087 (8)	0.0022 (8)
C31	0.0193 (11)	0.0188 (11)	0.0215 (12)	0.0001 (9)	0.0040 (9)	0.0011 (9)
C32	0.0219 (12)	0.0182 (11)	0.0199 (12)	0.0021 (9)	0.0066 (9)	−0.0004 (9)
C33	0.0233 (12)	0.0267 (13)	0.0209 (12)	−0.0009 (10)	0.0080 (9)	0.0017 (10)
C34	0.0277 (13)	0.0223 (12)	0.0311 (14)	−0.0022 (10)	0.0050 (10)	0.0068 (11)
C35	0.0286 (13)	0.0171 (12)	0.0295 (13)	−0.0005 (10)	0.0059 (10)	−0.0038 (10)
C36	0.0260 (13)	0.0199 (12)	0.0209 (12)	0.0007 (9)	0.0062 (9)	−0.0021 (9)
C37	0.0238 (12)	0.0179 (11)	0.0201 (12)	0.0023 (9)	0.0059 (9)	−0.0014 (9)
C38	0.0220 (12)	0.0209 (12)	0.0188 (12)	−0.0001 (9)	0.0055 (9)	−0.0001 (9)
C39	0.0235 (12)	0.0229 (12)	0.0211 (12)	−0.0007 (9)	0.0048 (9)	0.0022 (10)
C40	0.0304 (13)	0.0304 (14)	0.0178 (12)	−0.0023 (10)	0.0083 (10)	−0.0017 (10)

Geometric parameters (Å, º) top

S1—C10	1.759 (2)	S3—C28	1.760 (2)
S1—C8	1.770 (2)	S3—C30	1.771 (2)
O1—C6	1.354 (3)	O7—C22	1.362 (3)
O1—H1O	0.8404	O7—H3O	0.8400
O2—C9	1.224 (2)	O8—C29	1.223 (3)
O3—C10	1.218 (2)	O9—C30	1.211 (2)
N1—C10	1.368 (3)	N3—C29	1.373 (3)
N1—C9	1.379 (3)	N3—C30	1.376 (3)
N1—H1N	0.9104	N3—H3N	0.9104
C1—C6	1.406 (3)	C21—C26	1.402 (3)
C1—C2	1.409 (3)	C21—C22	1.413 (3)
C1—C7	1.452 (3)	C21—C27	1.452 (3)
C2—C3	1.375 (3)	C22—C23	1.385 (3)
C2—H2	0.9500	C23—C24	1.380 (3)
C3—C4	1.395 (3)	C23—H23	0.9500
C3—H3	0.9500	C24—C25	1.385 (3)
C4—C5	1.373 (3)	C24—H24	0.9500
C4—H4	0.9500	C25—C26	1.383 (3)
C5—C6	1.389 (3)	C25—H25	0.9500
C5—H5	0.9500	C26—H26	0.9500
C7—C8	1.331 (3)	C27—C28	1.344 (3)
C7—H7	0.9500	C27—H27	0.9500
C8—C9	1.488 (3)	C28—C29	1.483 (3)
S2—C18	1.758 (2)	S4—C38	1.754 (2)
S2—C20	1.769 (2)	S4—C40	1.770 (2)
O4—C12	1.365 (2)	O10—C32	1.357 (2)
O4—H2O	0.8403	O10—H4O	0.8399
O5—C19	1.228 (2)	O11—C39	1.218 (3)
O6—C20	1.210 (2)	O12—C40	1.205 (3)
N2—C20	1.374 (3)	N4—C40	1.372 (3)
N2—C19	1.377 (3)	N4—C39	1.382 (3)
N2—H2N	0.9093	N4—H4N	0.9104
C11—C16	1.407 (3)	C31—C36	1.407 (3)
C11—C12	1.409 (3)	C31—C32	1.412 (3)
C11—C17	1.450 (3)	C31—C37	1.455 (3)
C12—C13	1.395 (3)	C32—C33	1.391 (3)
C13—C14	1.369 (3)	C33—C34	1.378 (3)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.388 (3)	C34—C35	1.397 (3)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.380 (3)	C35—C36	1.373 (3)
C15—H15	0.9500	C35—H35	0.9500
C16—H16	0.9500	C36—H36	0.9500
C17—C18	1.346 (3)	C37—C38	1.344 (3)
C17—H17	0.9500	C37—H37	0.9500
C18—C19	1.471 (3)	C38—C39	1.483 (3)

C10—S1—C8	91.68 (10)	C28—S3—C30	91.93 (10)
C6—O1—H1O	116.9	C22—O7—H3O	109.6
C10—N1—C9	117.22 (19)	C29—N3—C30	117.45 (19)
C10—N1—H1N	122.4	C29—N3—H3N	120.3
C9—N1—H1N	119.8	C30—N3—H3N	122.1
C6—C1—C2	117.1 (2)	C26—C21—C22	116.9 (2)
C6—C1—C7	118.6 (2)	C26—C21—C27	124.8 (2)
C2—C1—C7	124.3 (2)	C22—C21—C27	118.3 (2)
C3—C2—C1	121.8 (2)	O7—C22—C23	122.3 (2)
C3—C2—H2	119.1	O7—C22—C21	116.7 (2)
C1—C2—H2	119.1	C23—C22—C21	121.0 (2)
C2—C3—C4	119.8 (2)	C24—C23—C22	119.9 (2)
C2—C3—H3	120.1	C24—C23—H23	120.1
C4—C3—H3	120.1	C22—C23—H23	120.1
C5—C4—C3	119.9 (2)	C23—C24—C25	120.9 (2)
C5—C4—H4	120.0	C23—C24—H24	119.5
C3—C4—H4	120.0	C25—C24—H24	119.5
C4—C5—C6	120.5 (2)	C26—C25—C24	118.9 (2)
C4—C5—H5	119.8	C26—C25—H25	120.5
C6—C5—H5	119.8	C24—C25—H25	120.5
O1—C6—C5	121.8 (2)	C25—C26—C21	122.3 (2)
O1—C6—C1	117.2 (2)	C25—C26—H26	118.9
C5—C6—C1	121.0 (2)	C21—C26—H26	118.9
C8—C7—C1	131.2 (2)	C28—C27—C21	130.3 (2)
C8—C7—H7	114.4	C28—C27—H27	114.9
C1—C7—H7	114.4	C21—C27—H27	114.9
C7—C8—C9	121.54 (19)	C27—C28—C29	120.5 (2)
C7—C8—S1	129.03 (17)	C27—C28—S3	129.85 (18)
C9—C8—S1	109.41 (15)	C29—C28—S3	109.61 (15)
O2—C9—N1	123.5 (2)	O8—C29—N3	123.4 (2)
O2—C9—C8	126.0 (2)	O8—C29—C28	125.8 (2)
N1—C9—C8	110.46 (18)	N3—C29—C28	110.74 (19)
O3—C10—N1	125.1 (2)	O9—C30—N3	125.5 (2)
O3—C10—S1	123.85 (18)	O9—C30—S3	124.39 (19)
N1—C10—S1	111.07 (16)	N3—C30—S3	110.10 (15)
C18—S2—C20	91.79 (10)	C38—S4—C40	91.88 (11)
C12—O4—H2O	100.4	C32—O10—H4O	108.3
C20—N2—C19	117.47 (19)	C40—N4—C39	117.62 (19)
C20—N2—H2N	118.7	C40—N4—H4N	121.3
C19—N2—H2N	123.8	C39—N4—H4N	121.0
C16—C11—C12	116.9 (2)	C36—C31—C32	117.46 (19)
C16—C11—C17	124.3 (2)	C36—C31—C37	124.5 (2)
C12—C11—C17	118.78 (19)	C32—C31—C37	118.0 (2)
O4—C12—C13	122.1 (2)	O10—C32—C33	121.60 (19)
O4—C12—C11	116.80 (19)	O10—C32—C31	117.65 (19)
C13—C12—C11	121.1 (2)	C33—C32—C31	120.7 (2)
C14—C13—C12	120.0 (2)	C34—C33—C32	120.1 (2)
C14—C13—H13	120.0	C34—C33—H33	120.0
C12—C13—H13	120.0	C32—C33—H33	120.0
C13—C14—C15	120.7 (2)	C33—C34—C35	120.3 (2)
C13—C14—H14	119.6	C33—C34—H34	119.8
C15—C14—H14	119.6	C35—C34—H34	119.8
C16—C15—C14	119.4 (2)	C36—C35—C34	119.7 (2)
C16—C15—H15	120.3	C36—C35—H35	120.1
C14—C15—H15	120.3	C34—C35—H35	120.1
C15—C16—C11	121.9 (2)	C35—C36—C31	121.7 (2)
C15—C16—H16	119.0	C35—C36—H36	119.2
C11—C16—H16	119.0	C31—C36—H36	119.2
C18—C17—C11	131.5 (2)	C38—C37—C31	130.7 (2)
C18—C17—H17	114.2	C38—C37—H37	114.7
C11—C17—H17	114.2	C31—C37—H37	114.7
C17—C18—C19	120.88 (19)	C37—C38—C39	120.8 (2)
C17—C18—S2	129.02 (17)	C37—C38—S4	128.92 (18)
C19—C18—S2	110.10 (15)	C39—C38—S4	110.26 (15)
O5—C19—N2	123.4 (2)	O11—C39—N4	123.4 (2)
O5—C19—C18	126.0 (2)	O11—C39—C38	126.6 (2)
N2—C19—C18	110.57 (19)	N4—C39—C38	110.0 (2)
O6—C20—N2	125.5 (2)	O12—C40—N4	125.5 (2)
O6—C20—S2	124.48 (18)	O12—C40—S4	124.3 (2)
N2—C20—S2	110.04 (16)	N4—C40—S4	110.20 (16)

C6—C1—C2—C3	1.1 (3)	C26—C21—C22—O7	−179.87 (19)
C7—C1—C2—C3	−178.1 (2)	C27—C21—C22—O7	−0.7 (3)
C1—C2—C3—C4	−0.2 (4)	C26—C21—C22—C23	0.7 (3)
C2—C3—C4—C5	−0.1 (4)	C27—C21—C22—C23	179.8 (2)
C3—C4—C5—C6	−0.4 (4)	O7—C22—C23—C24	179.6 (2)
C4—C5—C6—O1	179.6 (2)	C21—C22—C23—C24	−0.9 (4)
C4—C5—C6—C1	1.3 (4)	C22—C23—C24—C25	0.2 (4)
C2—C1—C6—O1	−179.96 (19)	C23—C24—C25—C26	0.8 (4)
C7—C1—C6—O1	−0.8 (3)	C24—C25—C26—C21	−1.0 (4)
C2—C1—C6—C5	−1.6 (3)	C22—C21—C26—C25	0.3 (3)
C7—C1—C6—C5	177.6 (2)	C27—C21—C26—C25	−178.8 (2)
C6—C1—C7—C8	−178.6 (2)	C26—C21—C27—C28	−8.9 (4)
C2—C1—C7—C8	0.5 (4)	C22—C21—C27—C28	172.0 (2)
C1—C7—C8—C9	−177.5 (2)	C21—C27—C28—C29	180.0 (2)
C1—C7—C8—S1	0.8 (4)	C21—C27—C28—S3	−2.1 (4)
C10—S1—C8—C7	−174.7 (2)	C30—S3—C28—C27	178.1 (2)
C10—S1—C8—C9	3.77 (16)	C30—S3—C28—C29	−3.85 (16)
C10—N1—C9—O2	−180.0 (2)	C30—N3—C29—O8	179.0 (2)
C10—N1—C9—C8	1.5 (3)	C30—N3—C29—C28	−0.6 (3)
C7—C8—C9—O2	−3.5 (3)	C27—C28—C29—O8	2.0 (3)
S1—C8—C9—O2	177.87 (19)	S3—C28—C29—O8	−176.31 (18)
C7—C8—C9—N1	175.0 (2)	C27—C28—C29—N3	−178.43 (19)
S1—C8—C9—N1	−3.7 (2)	S3—C28—C29—N3	3.3 (2)
C9—N1—C10—O3	−179.6 (2)	C29—N3—C30—O9	177.5 (2)
C9—N1—C10—S1	1.4 (3)	C29—N3—C30—S3	−2.3 (2)
C8—S1—C10—O3	177.9 (2)	C28—S3—C30—O9	−176.3 (2)
C8—S1—C10—N1	−3.04 (17)	C28—S3—C30—N3	3.57 (17)
C16—C11—C12—O4	−179.87 (18)	C36—C31—C32—O10	−179.76 (19)
C17—C11—C12—O4	0.2 (3)	C37—C31—C32—O10	−2.1 (3)
C16—C11—C12—C13	0.3 (3)	C36—C31—C32—C33	−0.7 (3)
C17—C11—C12—C13	−179.60 (19)	C37—C31—C32—C33	176.92 (19)
O4—C12—C13—C14	179.5 (2)	O10—C32—C33—C34	179.8 (2)
C11—C12—C13—C14	−0.7 (3)	C31—C32—C33—C34	0.8 (3)
C12—C13—C14—C15	1.0 (4)	C32—C33—C34—C35	−0.3 (3)
C13—C14—C15—C16	−0.9 (4)	C33—C34—C35—C36	−0.2 (3)
C14—C15—C16—C11	0.5 (4)	C34—C35—C36—C31	0.2 (3)
C12—C11—C16—C15	−0.2 (3)	C32—C31—C36—C35	0.2 (3)
C17—C11—C16—C15	179.7 (2)	C37—C31—C36—C35	−177.2 (2)
C16—C11—C17—C18	0.1 (4)	C36—C31—C37—C38	−2.8 (4)
C12—C11—C17—C18	−180.0 (2)	C32—C31—C37—C38	179.8 (2)
C11—C17—C18—C19	179.9 (2)	C31—C37—C38—C39	176.4 (2)
C11—C17—C18—S2	0.2 (4)	C31—C37—C38—S4	−3.4 (4)
C20—S2—C18—C17	178.4 (2)	C40—S4—C38—C37	−179.0 (2)
C20—S2—C18—C19	−1.28 (16)	C40—S4—C38—C39	1.07 (17)
C20—N2—C19—O5	179.6 (2)	C40—N4—C39—O11	179.9 (2)
C20—N2—C19—C18	0.3 (3)	C40—N4—C39—C38	−0.9 (3)
C17—C18—C19—O5	1.9 (3)	C37—C38—C39—O11	−1.0 (4)
S2—C18—C19—O5	−178.41 (18)	S4—C38—C39—O11	178.9 (2)
C17—C18—C19—N2	−178.90 (19)	C37—C38—C39—N4	179.8 (2)
S2—C18—C19—N2	0.8 (2)	S4—C38—C39—N4	−0.3 (2)
C19—N2—C20—O6	178.2 (2)	C39—N4—C40—O12	−178.2 (2)
C19—N2—C20—S2	−1.3 (2)	C39—N4—C40—S4	1.7 (3)
C18—S2—C20—O6	−178.1 (2)	C38—S4—C40—O12	178.3 (2)
C18—S2—C20—N2	1.45 (16)	C38—S4—C40—N4	−1.56 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5ⁱ	0.91	1.91	2.819 (2)	175
O1—H1O···O12ⁱⁱ	0.84	1.91	2.744 (2)	175
N2—H2N···O2ⁱⁱⁱ	0.91	1.96	2.859 (2)	169
O4—H2O···O9^iv	0.84	1.97	2.759 (2)	156
N3—H3N···O11^v	0.91	1.95	2.859 (2)	177
O7—H3O···O6ⁱ	0.84	1.94	2.757 (2)	166
N4—H4N···O8^vi	0.91	1.93	2.843 (2)	176
O10—H4O···O3^vii	0.84	1.89	2.722 (2)	169

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5ⁱ	0.91	1.91	2.819 (2)	175
O1—H1O···O12ⁱⁱ	0.84	1.91	2.744 (2)	175
N2—H2N···O2ⁱⁱⁱ	0.91	1.96	2.859 (2)	169
O4—H2O···O9^iv	0.84	1.97	2.759 (2)	156
N3—H3N···O11^v	0.91	1.95	2.859 (2)	177
O7—H3O···O6ⁱ	0.84	1.94	2.757 (2)	166
N4—H4N···O8^vi	0.91	1.93	2.843 (2)	176
O10—H4O···O3^vii	0.84	1.89	2.722 (2)	169

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

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

Behbehani, H. & Ibrahim, H. M. (2012). Molecules, 17, 6362–6385. Web of Science CSD CrossRef CAS PubMed Google Scholar
Bondock, S., Khalifa, W. & Fadda, A. A. (2007). Eur. J. Med. Chem. 42, 948–954. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2015). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Singh, S. P., Parmar, S. S., Raman, K. & Stenberg, V. I. (1981). Chem. Rev. 81, 175–203. CrossRef CAS Web of Science Google Scholar
Vicini, P., Geronikaki, A., Incerti, M., Zani, F., Dearden, J. & Hewitt, M. (2008). Bioorg. Med. Chem. 16, 3714–3724. Web of Science CrossRef PubMed CAS Google Scholar

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o965-o966

https://doi.org/10.1107/S2056989015021908

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (5Z)-5-(2-hy­dr­oxy­benzyl­­idene)-1,3-thia­zolidine-2,4-dione

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (5Z)-5-(2-hydroxybenzylidene)-1,3-thiazolidine-2,4-dione