(Z)-3-(4-Chloro-phen-yl)-2-(2-phenyl-cyclo-hex-2-en-1-yl-imino)-thia-zolidin-4-one.

The title compound, C(21)H(19)ClN(2)OS, exists in a cis conformation with respect to the N=C bond [1.2608 (13) Å]. The cyclo-hexene ring adopts a distorted half-chair conformation. The thia-zolidine ring is close to being planar (r.m.s. deviation = 0.057 Å) and makes dihedral angles of 62.92 (6) and 56.32 (6)°, respectively, with the benzene ring and the chloro-substituted benzene ring. The dihedral angle between the benzene ring and the chloro-substituted benzene ring is 72.91 (6)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N hydrogen bonds into undulating sheets lying parallel to the bc plane. 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 et al. (2000 ▶); Kato et al. (1999a ▶,b ▶); Tanabe et al. (1991 ▶); Rawal et al. (2005 ▶); Voss et al. (2003 ▶). For related structures, see: Fun et al. (2011 ▶); Ooi et al. (2012 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H19ClN2OS

M = 382.89

Monoclinic,

a = 9.1139 (3) Å

b = 17.4562 (6) Å

c = 12.9246 (4) Å

β = 118.640 (2)°

V = 1804.64 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.37 × 0.25 × 0.18 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.886, T max = 0.942

23788 measured reflections

5231 independent reflections

4605 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.05

5231 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.42 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/S1600536812024294/hb6814sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024294/hb6814Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024294/hb6814Isup3.cml

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

C21H19ClN2OS	F(000) = 800
Mr = 382.89	Dx = 1.409 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9952 reflections
a = 9.1139 (3) Å	θ = 2.6–34.3°
b = 17.4562 (6) Å	µ = 0.34 mm−1
c = 12.9246 (4) Å	T = 100 K
β = 118.640 (2)°	Block, colourless
V = 1804.64 (10) Å3	0.37 × 0.25 × 0.18 mm
Z = 4

Bruker APEX DUO CCD diffractometer	5231 independent reflections
Radiation source: fine-focus sealed tube	4605 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.886, Tmax = 0.942	k = −24→24
23788 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0385P)2 + 0.767P] where P = (Fo2 + 2Fc2)/3
5231 reflections	(Δ/σ)max = 0.002
235 parameters	Δρmax = 0.42 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
Cl1	0.21570 (4)	−0.051642 (15)	1.02340 (2)	0.02160 (7)
S1	0.24459 (4)	0.363135 (15)	0.69867 (2)	0.01731 (7)
O1	0.04486 (10)	0.16687 (5)	0.56961 (7)	0.01895 (16)
N1	0.27625 (11)	0.31077 (5)	0.90882 (7)	0.01307 (16)
N2	0.18040 (11)	0.22633 (5)	0.74984 (7)	0.01253 (16)
C1	0.63915 (13)	0.29044 (6)	1.06753 (10)	0.0170 (2)
H1A	0.6105	0.3130	0.9933	0.020*
C2	0.75211 (14)	0.22981 (7)	1.10844 (11)	0.0220 (2)
H2A	0.7990	0.2111	1.0617	0.026*
C3	0.79679 (15)	0.19637 (7)	1.21700 (12)	0.0277 (3)
H3A	0.8734	0.1548	1.2444	0.033*
C4	0.72833 (16)	0.22428 (8)	1.28510 (12)	0.0282 (3)
H4A	0.7600	0.2024	1.3602	0.034*
C5	0.61355 (15)	0.28412 (7)	1.24385 (10)	0.0219 (2)
H5A	0.5658	0.3019	1.2906	0.026*
C6	0.56708 (13)	0.31871 (6)	1.13445 (9)	0.01562 (19)
C7	0.44377 (13)	0.38247 (6)	1.08949 (9)	0.01487 (19)
C8	0.43293 (14)	0.43351 (7)	1.16306 (10)	0.0214 (2)
H8A	0.5073	0.4276	1.2450	0.026*
C9	0.31193 (16)	0.49927 (7)	1.12570 (11)	0.0255 (2)
H9A	0.3714	0.5460	1.1689	0.031*
H9B	0.2233	0.4879	1.1470	0.031*
C10	0.23143 (15)	0.51445 (6)	0.99322 (11)	0.0214 (2)
H10A	0.1324	0.5478	0.9685	0.026*
H10B	0.3120	0.5411	0.9748	0.026*
C11	0.17912 (13)	0.43895 (6)	0.92644 (9)	0.01592 (19)
H11A	0.1197	0.4492	0.8406	0.019*
H11B	0.1013	0.4118	0.9470	0.019*
C12	0.33162 (13)	0.38816 (6)	0.95671 (9)	0.01352 (18)
H12A	0.3971	0.4107	0.9204	0.016*
C13	0.23863 (12)	0.29844 (6)	0.80285 (9)	0.01265 (18)
C14	0.15339 (14)	0.29402 (6)	0.58042 (9)	0.0176 (2)
H14A	0.0486	0.3146	0.5151	0.021*
H14B	0.2318	0.2828	0.5496	0.021*
C15	0.11748 (13)	0.22186 (6)	0.62889 (9)	0.01409 (18)
C16	0.18581 (12)	0.16066 (6)	0.81802 (8)	0.01233 (18)
C17	0.04100 (13)	0.11881 (6)	0.78834 (9)	0.01434 (18)
H17A	−0.0632	0.1350	0.7254	0.017*
C18	0.05075 (14)	0.05291 (6)	0.85211 (9)	0.01572 (19)
H18A	−0.0464	0.0232	0.8324	0.019*
C19	0.20399 (14)	0.03118 (6)	0.94472 (9)	0.01523 (19)
C20	0.34831 (13)	0.07366 (6)	0.97650 (9)	0.01584 (19)
H20A	0.4516	0.0586	1.0415	0.019*
C21	0.33872 (13)	0.13850 (6)	0.91151 (9)	0.01426 (18)
H21A	0.4364	0.1678	0.9308	0.017*

	U11	U22	U33	U12	U13	U23
Cl1	0.02893 (14)	0.01406 (12)	0.02091 (13)	0.00025 (10)	0.01122 (11)	0.00494 (9)
S1	0.02495 (14)	0.01306 (12)	0.01514 (12)	−0.00279 (9)	0.01059 (10)	0.00118 (9)
O1	0.0237 (4)	0.0184 (4)	0.0148 (3)	−0.0037 (3)	0.0093 (3)	−0.0040 (3)
N1	0.0136 (4)	0.0108 (4)	0.0129 (4)	−0.0009 (3)	0.0049 (3)	−0.0001 (3)
N2	0.0156 (4)	0.0107 (4)	0.0104 (4)	−0.0015 (3)	0.0054 (3)	0.0001 (3)
C1	0.0138 (4)	0.0152 (5)	0.0193 (5)	−0.0023 (4)	0.0058 (4)	−0.0026 (4)
C2	0.0135 (5)	0.0173 (5)	0.0327 (6)	−0.0014 (4)	0.0090 (4)	−0.0048 (4)
C3	0.0154 (5)	0.0196 (6)	0.0383 (7)	0.0030 (4)	0.0051 (5)	0.0053 (5)
C4	0.0227 (6)	0.0273 (6)	0.0253 (6)	0.0023 (5)	0.0041 (5)	0.0089 (5)
C5	0.0188 (5)	0.0248 (6)	0.0184 (5)	0.0007 (4)	0.0059 (4)	0.0025 (4)
C6	0.0122 (4)	0.0149 (5)	0.0157 (4)	−0.0018 (4)	0.0034 (4)	−0.0015 (4)
C7	0.0127 (4)	0.0149 (5)	0.0143 (4)	−0.0010 (4)	0.0043 (4)	−0.0012 (4)
C8	0.0194 (5)	0.0224 (5)	0.0171 (5)	0.0011 (4)	0.0045 (4)	−0.0055 (4)
C9	0.0251 (6)	0.0211 (6)	0.0260 (6)	0.0029 (5)	0.0088 (5)	−0.0091 (4)
C10	0.0212 (5)	0.0129 (5)	0.0277 (6)	0.0013 (4)	0.0096 (4)	−0.0018 (4)
C11	0.0156 (4)	0.0126 (4)	0.0164 (4)	0.0015 (4)	0.0050 (4)	0.0015 (4)
C12	0.0148 (4)	0.0107 (4)	0.0133 (4)	−0.0016 (3)	0.0053 (4)	−0.0008 (3)
C13	0.0126 (4)	0.0107 (4)	0.0139 (4)	−0.0001 (3)	0.0057 (3)	0.0013 (3)
C14	0.0244 (5)	0.0163 (5)	0.0137 (4)	−0.0018 (4)	0.0103 (4)	0.0002 (4)
C15	0.0150 (4)	0.0160 (5)	0.0124 (4)	0.0007 (4)	0.0075 (4)	−0.0002 (3)
C16	0.0154 (4)	0.0103 (4)	0.0113 (4)	0.0003 (3)	0.0064 (3)	−0.0002 (3)
C17	0.0145 (4)	0.0146 (4)	0.0122 (4)	−0.0008 (4)	0.0050 (3)	−0.0008 (3)
C18	0.0176 (5)	0.0144 (5)	0.0149 (4)	−0.0038 (4)	0.0076 (4)	−0.0019 (4)
C19	0.0222 (5)	0.0100 (4)	0.0143 (4)	0.0010 (4)	0.0093 (4)	0.0008 (3)
C20	0.0162 (4)	0.0142 (5)	0.0153 (4)	0.0034 (4)	0.0061 (4)	0.0008 (4)
C21	0.0133 (4)	0.0132 (4)	0.0156 (4)	−0.0001 (3)	0.0064 (4)	−0.0009 (3)

Cl1—C19	1.7411 (11)	C8—H8A	0.9500
S1—C13	1.7780 (10)	C9—C10	1.5284 (18)
S1—C14	1.8067 (11)	C9—H9A	0.9900
O1—C15	1.2084 (13)	C9—H9B	0.9900
N1—C13	1.2608 (13)	C10—C11	1.5215 (15)
N1—C12	1.4707 (13)	C10—H10A	0.9900
N2—C15	1.3854 (12)	C10—H10B	0.9900
N2—C13	1.4096 (13)	C11—C12	1.5329 (14)
N2—C16	1.4322 (13)	C11—H11A	0.9900
C1—C2	1.3921 (15)	C11—H11B	0.9900
C1—C6	1.4027 (15)	C12—H12A	1.0000
C1—H1A	0.9500	C14—C15	1.5110 (15)
C2—C3	1.3883 (19)	C14—H14A	0.9900
C2—H2A	0.9500	C14—H14B	0.9900
C3—C4	1.388 (2)	C16—C17	1.3920 (14)
C3—H3A	0.9500	C16—C21	1.3920 (14)
C4—C5	1.3911 (17)	C17—C18	1.3929 (14)
C4—H4A	0.9500	C17—H17A	0.9500
C5—C6	1.4032 (15)	C18—C19	1.3873 (15)
C5—H5A	0.9500	C18—H18A	0.9500
C6—C7	1.4878 (15)	C19—C20	1.3895 (15)
C7—C8	1.3408 (15)	C20—C21	1.3871 (14)
C7—C12	1.5226 (14)	C20—H20A	0.9500
C8—C9	1.5021 (17)	C21—H21A	0.9500
C13—S1—C14	92.74 (5)	C10—C11—H11A	109.5
C13—N1—C12	118.28 (9)	C12—C11—H11A	109.5
C15—N2—C13	117.03 (8)	C10—C11—H11B	109.5
C15—N2—C16	121.51 (8)	C12—C11—H11B	109.5
C13—N2—C16	121.45 (8)	H11A—C11—H11B	108.0
C2—C1—C6	120.85 (11)	N1—C12—C7	108.91 (8)
C2—C1—H1A	119.6	N1—C12—C11	109.73 (8)
C6—C1—H1A	119.6	C7—C12—C11	111.23 (8)
C3—C2—C1	120.59 (11)	N1—C12—H12A	109.0
C3—C2—H2A	119.7	C7—C12—H12A	109.0
C1—C2—H2A	119.7	C11—C12—H12A	109.0
C2—C3—C4	119.33 (11)	N1—C13—N2	121.56 (9)
C2—C3—H3A	120.3	N1—C13—S1	128.54 (8)
C4—C3—H3A	120.3	N2—C13—S1	109.89 (7)
C3—C4—C5	120.29 (12)	C15—C14—S1	108.01 (7)
C3—C4—H4A	119.9	C15—C14—H14A	110.1
C5—C4—H4A	119.9	S1—C14—H14A	110.1
C4—C5—C6	121.17 (12)	C15—C14—H14B	110.1
C4—C5—H5A	119.4	S1—C14—H14B	110.1
C6—C5—H5A	119.4	H14A—C14—H14B	108.4
C1—C6—C5	117.75 (10)	O1—C15—N2	124.39 (10)
C1—C6—C7	120.77 (10)	O1—C15—C14	124.13 (9)
C5—C6—C7	121.48 (10)	N2—C15—C14	111.47 (9)
C8—C7—C6	121.25 (10)	C17—C16—C21	121.06 (9)
C8—C7—C12	121.21 (10)	C17—C16—N2	120.14 (9)
C6—C7—C12	117.54 (9)	C21—C16—N2	118.78 (9)
C7—C8—C9	124.89 (10)	C16—C17—C18	119.16 (9)
C7—C8—H8A	117.6	C16—C17—H17A	120.4
C9—C8—H8A	117.6	C18—C17—H17A	120.4
C8—C9—C10	112.15 (10)	C19—C18—C17	119.25 (10)
C8—C9—H9A	109.2	C19—C18—H18A	120.4
C10—C9—H9A	109.2	C17—C18—H18A	120.4
C8—C9—H9B	109.2	C18—C19—C20	121.87 (10)
C10—C9—H9B	109.2	C18—C19—Cl1	119.04 (8)
H9A—C9—H9B	107.9	C20—C19—Cl1	119.09 (8)
C11—C10—C9	109.69 (10)	C21—C20—C19	118.72 (10)
C11—C10—H10A	109.7	C21—C20—H20A	120.6
C9—C10—H10A	109.7	C19—C20—H20A	120.6
C11—C10—H10B	109.7	C20—C21—C16	119.91 (10)
C9—C10—H10B	109.7	C20—C21—H21A	120.0
H10A—C10—H10B	108.2	C16—C21—H21A	120.0
C10—C11—C12	110.92 (9)
C6—C1—C2—C3	−0.49 (17)	C15—N2—C13—N1	170.00 (9)
C1—C2—C3—C4	−0.36 (18)	C16—N2—C13—N1	−9.89 (15)
C2—C3—C4—C5	1.30 (19)	C15—N2—C13—S1	−9.15 (11)
C3—C4—C5—C6	−1.42 (19)	C16—N2—C13—S1	170.96 (7)
C2—C1—C6—C5	0.38 (16)	C14—S1—C13—N1	−175.13 (10)
C2—C1—C6—C7	−178.76 (10)	C14—S1—C13—N2	3.95 (8)
C4—C5—C6—C1	0.56 (17)	C13—S1—C14—C15	1.41 (8)
C4—C5—C6—C7	179.69 (11)	C13—N2—C15—O1	−170.49 (10)
C1—C6—C7—C8	−147.73 (11)	C16—N2—C15—O1	9.40 (16)
C5—C6—C7—C8	33.17 (16)	C13—N2—C15—C14	10.39 (13)
C1—C6—C7—C12	31.62 (14)	C16—N2—C15—C14	−169.72 (9)
C5—C6—C7—C12	−147.49 (10)	S1—C14—C15—O1	174.28 (9)
C6—C7—C8—C9	−179.63 (11)	S1—C14—C15—N2	−6.60 (11)
C12—C7—C8—C9	1.05 (18)	C15—N2—C16—C17	−54.52 (13)
C7—C8—C9—C10	−14.39 (18)	C13—N2—C16—C17	125.37 (10)
C8—C9—C10—C11	44.28 (14)	C15—N2—C16—C21	123.55 (10)
C9—C10—C11—C12	−63.22 (12)	C13—N2—C16—C21	−56.56 (13)
C13—N1—C12—C7	−153.55 (9)	C21—C16—C17—C18	−1.28 (15)
C13—N1—C12—C11	84.48 (11)	N2—C16—C17—C18	176.74 (9)
C8—C7—C12—N1	−139.34 (11)	C16—C17—C18—C19	0.93 (15)
C6—C7—C12—N1	41.32 (12)	C17—C18—C19—C20	0.53 (16)
C8—C7—C12—C11	−18.28 (14)	C17—C18—C19—Cl1	−179.52 (8)
C6—C7—C12—C11	162.38 (9)	C18—C19—C20—C21	−1.63 (16)
C10—C11—C12—N1	169.61 (9)	Cl1—C19—C20—C21	178.41 (8)
C10—C11—C12—C7	49.04 (12)	C19—C20—C21—C16	1.27 (15)
C12—N1—C13—N2	−178.32 (9)	C17—C16—C21—C20	0.16 (15)
C12—N1—C13—S1	0.66 (14)	N2—C16—C21—C20	−177.89 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.99	2.53	3.4814 (17)	161
C11—H11B···O1ii	0.99	2.33	3.2411 (14)	152
C14—H14B···N1iii	0.99	2.62	3.4496 (14)	141
C17—H17A···Cg1iv	0.95	2.81	3.5913 (13)	140

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
C10—H10A⋯O1i	0.99	2.53	3.4814 (17)	161
C11—H11B⋯O1ii	0.99	2.33	3.2411 (14)	152
C14—H14B⋯N1iii	0.99	2.62	3.4496 (14)	141
C17—H17A⋯Cg1iv	0.95	2.81	3.5913 (13)	140

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