(Z)-3-(4-Methyl-phen-yl)-2-[(2-phenyl-cyclo-hex-2-en-1-yl)imino]-1,3-thia-zol-idin-4-one.

The title compound, C(22)H(22)N(2)OS, exists in a cis conformation with respect to the N=C bond. The cyclo-hexene ring adopts a distorted sofa conformation. The thia-zolidine ring is essentially planar with a maximum deviation of 0.025 (2) Å and forms dihedral angles of 63.50 (7) and 57.52 (6)° with the benzene rings. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds, generating R(2) (2)(8) ring motifs, and forming infinite chains along the c axis. The crystal is further consolidated by C-H⋯π inter-actions.

Related literature

For details of thia­zolidin-4-one derivatives, see: Previtera et al. (1994 ▶); Sharma & Kumar (2000 ▶); Kato et al. (1999a ▶,b ▶); Tanabe et al. (1991 ▶); Rawal et al. (2005 ▶); Voss et al. (2003 ▶). For a related structure, see: Fun et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H22N2OS

M = 362.48

Monoclinic,

a = 9.2252 (4) Å

b = 17.6978 (8) Å

c = 12.8898 (4) Å

β = 119.289 (2)°

V = 1835.43 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.36 × 0.30 × 0.11 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.935, T max = 0.979

17337 measured reflections

5335 independent reflections

4496 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.100

S = 1.05

5335 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021691/bq2357sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021691/bq2357Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021691/bq2357Isup3.cml

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

C22H22N2OS	F(000) = 768
Mr = 362.48	Dx = 1.312 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7149 reflections
a = 9.2252 (4) Å	θ = 2.6–30.1°
b = 17.6978 (8) Å	µ = 0.19 mm−1
c = 12.8898 (4) Å	T = 100 K
β = 119.289 (2)°	Block, colorless
V = 1835.43 (13) Å3	0.36 × 0.30 × 0.11 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	5335 independent reflections
Radiation source: fine-focus sealed tube	4496 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→12
Tmin = 0.935, Tmax = 0.979	k = −24→24
17337 measured reflections	l = −18→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.5577P] where P = (Fo2 + 2Fc2)/3
5335 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100 (1) K.

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.25977 (4)	0.358936 (15)	0.31318 (2)	0.01799 (8)
O1	0.45923 (11)	0.16460 (5)	0.43965 (7)	0.01912 (17)
N1	0.22548 (12)	0.30934 (5)	0.10025 (8)	0.01374 (18)
N2	0.32300 (12)	0.22490 (5)	0.25893 (8)	0.01322 (17)
C1	−0.13978 (15)	0.28972 (6)	−0.05611 (10)	0.0187 (2)
H1A	−0.1117	0.3136	0.0155	0.022*
C2	−0.25218 (15)	0.22988 (7)	−0.09409 (12)	0.0234 (2)
H2A	−0.2979	0.2141	−0.0474	0.028*
C3	−0.29663 (17)	0.19352 (8)	−0.20098 (13)	0.0287 (3)
H3A	−0.3716	0.1536	−0.2260	0.034*
C4	−0.22788 (18)	0.21747 (8)	−0.27017 (12)	0.0304 (3)
H4A	−0.2581	0.1939	−0.3424	0.036*
C5	−0.11379 (16)	0.27669 (7)	−0.23182 (11)	0.0244 (3)
H5A	−0.0669	0.2915	−0.2781	0.029*
C6	−0.06845 (14)	0.31438 (6)	−0.12433 (10)	0.0174 (2)
C7	0.05345 (14)	0.37747 (6)	−0.08264 (10)	0.0163 (2)
C8	0.06412 (16)	0.42580 (7)	−0.15897 (11)	0.0227 (2)
H8A	−0.0077	0.4181	−0.2397	0.027*
C9	0.18230 (18)	0.49102 (7)	−0.12470 (12)	0.0264 (3)
H9A	0.1231	0.5352	−0.1704	0.032*
H9B	0.2688	0.4792	−0.1442	0.032*
C10	0.26201 (17)	0.50923 (6)	0.00802 (11)	0.0230 (2)
H10A	0.3574	0.5419	0.0312	0.028*
H10B	0.1827	0.5355	0.0239	0.028*
C11	0.31672 (15)	0.43625 (6)	0.07990 (10)	0.0169 (2)
H11A	0.3739	0.4482	0.1641	0.020*
H11B	0.3939	0.4096	0.0622	0.020*
C12	0.16769 (14)	0.38530 (6)	0.05117 (9)	0.0147 (2)
H12A	0.1046	0.4068	0.0870	0.018*
C13	0.26470 (13)	0.29626 (6)	0.20699 (9)	0.01284 (19)
C14	0.34921 (16)	0.28935 (6)	0.43065 (10)	0.0177 (2)
H14A	0.4507	0.3088	0.4968	0.021*
H14B	0.2719	0.2776	0.4590	0.021*
C15	0.38603 (14)	0.21927 (6)	0.38074 (9)	0.0145 (2)
C16	0.31678 (14)	0.16074 (6)	0.18854 (9)	0.01263 (19)
C17	0.45986 (14)	0.12024 (6)	0.21625 (9)	0.0150 (2)
H17A	0.5622	0.1356	0.2781	0.018*
C18	0.44769 (15)	0.05596 (6)	0.14971 (10)	0.0162 (2)
H18A	0.5429	0.0281	0.1686	0.019*
C19	0.29590 (15)	0.03267 (6)	0.05560 (10)	0.0158 (2)
C20	0.15440 (15)	0.07559 (6)	0.02786 (10)	0.0161 (2)
H20A	0.0526	0.0615	−0.0360	0.019*
C21	0.16391 (14)	0.13906 (6)	0.09446 (10)	0.0147 (2)
H21A	0.0688	0.1668	0.0762	0.018*
C22	0.28358 (17)	−0.03726 (6)	−0.01526 (11)	0.0216 (2)
H22A	0.3894	−0.0623	0.0201	0.032*
H22B	0.2519	−0.0232	−0.0955	0.032*
H22C	0.2016	−0.0707	−0.0154	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.02608 (16)	0.01403 (13)	0.01548 (13)	0.00194 (11)	0.01144 (12)	−0.00189 (9)
O1	0.0227 (4)	0.0196 (4)	0.0144 (4)	0.0029 (3)	0.0086 (3)	0.0039 (3)
N1	0.0142 (4)	0.0123 (4)	0.0127 (4)	0.0011 (3)	0.0050 (4)	0.0001 (3)
N2	0.0160 (4)	0.0119 (4)	0.0107 (4)	0.0013 (4)	0.0057 (4)	0.0000 (3)
C1	0.0143 (5)	0.0179 (5)	0.0201 (5)	0.0045 (4)	0.0055 (4)	0.0026 (4)
C2	0.0146 (5)	0.0204 (5)	0.0317 (6)	0.0025 (5)	0.0087 (5)	0.0046 (5)
C3	0.0160 (6)	0.0230 (6)	0.0357 (7)	−0.0027 (5)	0.0040 (5)	−0.0039 (5)
C4	0.0246 (6)	0.0316 (7)	0.0247 (6)	−0.0042 (6)	0.0042 (5)	−0.0092 (5)
C5	0.0214 (6)	0.0286 (6)	0.0185 (5)	−0.0005 (5)	0.0063 (5)	−0.0023 (5)
C6	0.0135 (5)	0.0178 (5)	0.0159 (5)	0.0028 (4)	0.0033 (4)	0.0020 (4)
C7	0.0141 (5)	0.0160 (5)	0.0151 (5)	0.0027 (4)	0.0044 (4)	0.0016 (4)
C8	0.0225 (6)	0.0236 (5)	0.0170 (5)	0.0011 (5)	0.0057 (5)	0.0050 (4)
C9	0.0285 (7)	0.0219 (6)	0.0255 (6)	−0.0005 (5)	0.0107 (5)	0.0092 (5)
C10	0.0254 (6)	0.0137 (5)	0.0284 (6)	−0.0002 (5)	0.0121 (5)	0.0021 (4)
C11	0.0178 (5)	0.0136 (4)	0.0171 (5)	−0.0007 (4)	0.0067 (4)	−0.0015 (4)
C12	0.0168 (5)	0.0119 (4)	0.0137 (5)	0.0019 (4)	0.0060 (4)	0.0007 (4)
C13	0.0126 (5)	0.0118 (4)	0.0133 (4)	−0.0013 (4)	0.0057 (4)	−0.0022 (4)
C14	0.0244 (6)	0.0168 (5)	0.0141 (5)	0.0000 (5)	0.0110 (5)	−0.0011 (4)
C15	0.0153 (5)	0.0164 (5)	0.0122 (5)	−0.0022 (4)	0.0072 (4)	−0.0009 (4)
C16	0.0161 (5)	0.0108 (4)	0.0115 (4)	0.0001 (4)	0.0070 (4)	0.0001 (3)
C17	0.0145 (5)	0.0164 (5)	0.0118 (4)	0.0007 (4)	0.0047 (4)	0.0008 (4)
C18	0.0181 (5)	0.0154 (5)	0.0157 (5)	0.0035 (4)	0.0089 (4)	0.0020 (4)
C19	0.0214 (6)	0.0122 (4)	0.0154 (5)	−0.0004 (4)	0.0103 (5)	−0.0001 (4)
C20	0.0160 (5)	0.0151 (5)	0.0153 (5)	−0.0026 (4)	0.0061 (4)	−0.0018 (4)
C21	0.0137 (5)	0.0136 (4)	0.0161 (5)	0.0010 (4)	0.0067 (4)	0.0007 (4)
C22	0.0280 (6)	0.0150 (5)	0.0241 (6)	−0.0016 (5)	0.0146 (5)	−0.0052 (4)

S1—C13	1.7796 (10)	C9—H9B	0.9700
S1—C14	1.8077 (11)	C10—C11	1.5244 (15)
O1—C15	1.2112 (13)	C10—H10A	0.9700
N1—C13	1.2611 (13)	C10—H10B	0.9700
N1—C12	1.4702 (13)	C11—C12	1.5305 (16)
N2—C15	1.3857 (13)	C11—H11A	0.9700
N2—C13	1.4072 (13)	C11—H11B	0.9700
N2—C16	1.4371 (12)	C12—H12A	0.9800
C1—C2	1.3928 (17)	C14—C15	1.5104 (14)
C1—C6	1.4010 (16)	C14—H14A	0.9700
C1—H1A	0.9300	C14—H14B	0.9700
C2—C3	1.3884 (19)	C16—C17	1.3865 (15)
C2—H2A	0.9300	C16—C21	1.3905 (15)
C3—C4	1.390 (2)	C17—C18	1.3957 (14)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.3935 (19)	C18—C19	1.3929 (16)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.4043 (16)	C19—C20	1.3971 (16)
C5—H5A	0.9300	C19—C22	1.5091 (15)
C6—C7	1.4863 (16)	C20—C21	1.3903 (14)
C7—C8	1.3431 (15)	C20—H20A	0.9300
C7—C12	1.5251 (15)	C21—H21A	0.9300
C8—C9	1.4983 (18)	C22—H22A	0.9600
C8—H8A	0.9300	C22—H22B	0.9600
C9—C10	1.5298 (18)	C22—H22C	0.9600
C9—H9A	0.9700
C13—S1—C14	92.68 (5)	C12—C11—H11B	109.4
C13—N1—C12	119.17 (9)	H11A—C11—H11B	108.0
C15—N2—C13	117.04 (8)	N1—C12—C7	107.95 (8)
C15—N2—C16	121.57 (9)	N1—C12—C11	109.93 (9)
C13—N2—C16	121.39 (8)	C7—C12—C11	111.66 (9)
C2—C1—C6	120.91 (11)	N1—C12—H12A	109.1
C2—C1—H1A	119.5	C7—C12—H12A	109.1
C6—C1—H1A	119.5	C11—C12—H12A	109.1
C3—C2—C1	120.59 (12)	N1—C13—N2	121.51 (9)
C3—C2—H2A	119.7	N1—C13—S1	128.54 (8)
C1—C2—H2A	119.7	N2—C13—S1	109.94 (7)
C2—C3—C4	119.32 (12)	C15—C14—S1	107.95 (7)
C2—C3—H3A	120.3	C15—C14—H14A	110.1
C4—C3—H3A	120.3	S1—C14—H14A	110.1
C3—C4—C5	120.29 (12)	C15—C14—H14B	110.1
C3—C4—H4A	119.9	S1—C14—H14B	110.1
C5—C4—H4A	119.9	H14A—C14—H14B	108.4
C4—C5—C6	121.06 (12)	O1—C15—N2	124.34 (10)
C4—C5—H5A	119.5	O1—C15—C14	124.16 (9)
C6—C5—H5A	119.5	N2—C15—C14	111.49 (9)
C1—C6—C5	117.82 (11)	C17—C16—C21	120.91 (10)
C1—C6—C7	120.77 (10)	C17—C16—N2	120.46 (10)
C5—C6—C7	121.40 (10)	C21—C16—N2	118.61 (10)
C8—C7—C6	121.81 (11)	C16—C17—C18	118.87 (10)
C8—C7—C12	120.86 (11)	C16—C17—H17A	120.6
C6—C7—C12	117.33 (9)	C18—C17—H17A	120.6
C7—C8—C9	125.32 (11)	C19—C18—C17	121.38 (10)
C7—C8—H8A	117.3	C19—C18—H18A	119.3
C9—C8—H8A	117.3	C17—C18—H18A	119.3
C8—C9—C10	111.99 (10)	C18—C19—C20	118.51 (10)
C8—C9—H9A	109.2	C18—C19—C22	121.05 (10)
C10—C9—H9A	109.2	C20—C19—C22	120.44 (11)
C8—C9—H9B	109.2	C21—C20—C19	120.82 (11)
C10—C9—H9B	109.2	C21—C20—H20A	119.6
H9A—C9—H9B	107.9	C19—C20—H20A	119.6
C11—C10—C9	109.65 (10)	C20—C21—C16	119.48 (10)
C11—C10—H10A	109.7	C20—C21—H21A	120.3
C9—C10—H10A	109.7	C16—C21—H21A	120.3
C11—C10—H10B	109.7	C19—C22—H22A	109.5
C9—C10—H10B	109.7	C19—C22—H22B	109.5
H10A—C10—H10B	108.2	H22A—C22—H22B	109.5
C10—C11—C12	111.17 (10)	C19—C22—H22C	109.5
C10—C11—H11A	109.4	H22A—C22—H22C	109.5
C12—C11—H11A	109.4	H22B—C22—H22C	109.5
C10—C11—H11B	109.4
C6—C1—C2—C3	−0.30 (18)	C15—N2—C13—N1	170.63 (10)
C1—C2—C3—C4	−0.06 (19)	C16—N2—C13—N1	−9.58 (16)
C2—C3—C4—C5	0.9 (2)	C15—N2—C13—S1	−8.88 (12)
C3—C4—C5—C6	−1.3 (2)	C16—N2—C13—S1	170.91 (8)
C2—C1—C6—C5	−0.13 (17)	C14—S1—C13—N1	−176.19 (11)
C2—C1—C6—C7	−179.04 (10)	C14—S1—C13—N2	3.28 (8)
C4—C5—C6—C1	0.94 (18)	C13—S1—C14—C15	2.27 (9)
C4—C5—C6—C7	179.84 (12)	C13—N2—C15—O1	−170.26 (10)
C1—C6—C7—C8	−147.19 (12)	C16—N2—C15—O1	9.95 (17)
C5—C6—C7—C8	33.94 (17)	C13—N2—C15—C14	10.80 (13)
C1—C6—C7—C12	33.08 (15)	C16—N2—C15—C14	−168.99 (10)
C5—C6—C7—C12	−145.79 (11)	S1—C14—C15—O1	173.60 (10)
C6—C7—C8—C9	179.62 (11)	S1—C14—C15—N2	−7.46 (12)
C12—C7—C8—C9	−0.66 (19)	C15—N2—C16—C17	−55.74 (14)
C7—C8—C9—C10	−14.03 (18)	C13—N2—C16—C17	124.48 (11)
C8—C9—C10—C11	44.52 (15)	C15—N2—C16—C21	122.51 (11)
C9—C10—C11—C12	−62.93 (13)	C13—N2—C16—C21	−57.26 (13)
C13—N1—C12—C7	−152.62 (10)	C21—C16—C17—C18	−1.47 (15)
C13—N1—C12—C11	85.36 (12)	N2—C16—C17—C18	176.74 (9)
C8—C7—C12—N1	−137.11 (11)	C16—C17—C18—C19	0.97 (15)
C6—C7—C12—N1	42.63 (12)	C17—C18—C19—C20	0.54 (15)
C8—C7—C12—C11	−16.16 (15)	C17—C18—C19—C22	−179.50 (10)
C6—C7—C12—C11	163.57 (9)	C18—C19—C20—C21	−1.59 (15)
C10—C11—C12—N1	167.43 (9)	C22—C19—C20—C21	178.45 (10)
C10—C11—C12—C7	47.65 (12)	C19—C20—C21—C16	1.12 (15)
C12—N1—C13—N2	−179.08 (10)	C17—C16—C21—C20	0.45 (15)
C12—N1—C13—S1	0.33 (16)	N2—C16—C21—C20	−177.80 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1i	0.97	2.35	3.2415 (14)	153
C14—H14B···N1ii	0.97	2.57	3.4020 (13)	143
C17—H17A···Cg1iii	0.93	2.86	3.6385 (14)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O1i	0.97	2.35	3.2415 (14)	153
C14—H14B⋯N1ii	0.97	2.57	3.4020 (13)	143
C17—H17A⋯Cg1iii	0.93	2.86	3.6385 (14)	142

Symmetry codes: (i) ; (ii) ; (iii) .