(Z)-3-Benzyl-2-[(2-phenyl-cyclo-hex-2-en-yl)imino]-1,3-thia-zolidin-4-one.

The title compound, C(22)H(22)N(2)OS, exists in a Z configuration 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 0.030 (2) Å, and forms dihedral angles of 76.66 (6) and 74.55 (6)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 71.55 (7)°. In the crystal, a C-H⋯π inter-action is observed.

Related literature

For the bioactivity of thia­zolidin-4-one derivatives, see: Previtera et al. (1994 ▶); Sharma et al. (2000 ▶); Kato, Ozaki & Tamura (1999 ▶); Kato, Ozaki & Ohi (1999 ▶); Tanabe et al. (1991 ▶); Rawal et al. (2005 ▶); Voss et al. (2003 ▶). For related structures, see: Fun et al. (2011 ▶); Ooi et al. (2012a ▶,b ▶,c ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H22N2OS

M = 362.48

Monoclinic,

a = 12.8400 (2) Å

b = 8.9261 (1) Å

c = 17.9634 (3) Å

β = 118.476 (1)°

V = 1809.72 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.39 × 0.32 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.929, T max = 0.960

22263 measured reflections

6670 independent reflections

4979 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.115

S = 1.03

6670 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.29 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/S1600536812033211/is5168sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033211/is5168Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033211/is5168Isup3.cml

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

C22H22N2OS	F(000) = 768
Mr = 362.48	Dx = 1.330 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6720 reflections
a = 12.8400 (2) Å	θ = 2.6–32.7°
b = 8.9261 (1) Å	µ = 0.19 mm−1
c = 17.9634 (3) Å	T = 100 K
β = 118.476 (1)°	Block, colourless
V = 1809.72 (5) Å3	0.39 × 0.32 × 0.21 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6670 independent reflections
Radiation source: fine-focus sealed tube	4979 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 32.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.929, Tmax = 0.960	k = −11→13
22263 measured reflections	l = −25→27

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.6514P] where P = (Fo2 + 2Fc2)/3
6670 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.29 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	0.36793 (3)	0.30018 (4)	0.40002 (2)	0.02412 (8)
O1	0.40661 (8)	0.70672 (11)	0.34194 (6)	0.0271 (2)
N1	0.16966 (8)	0.40320 (11)	0.40509 (6)	0.01676 (19)
N2	0.28594 (8)	0.57353 (12)	0.37911 (6)	0.01740 (19)
C1	0.27121 (10)	0.31490 (14)	0.59927 (8)	0.0202 (2)
H1A	0.3136	0.2657	0.5767	0.024*
C2	0.33166 (11)	0.38392 (16)	0.67770 (8)	0.0246 (3)
H2A	0.4139	0.3781	0.7078	0.030*
C3	0.27033 (12)	0.46163 (16)	0.71150 (8)	0.0260 (3)
H3A	0.3110	0.5091	0.7637	0.031*
C4	0.14737 (12)	0.46752 (16)	0.66629 (8)	0.0251 (3)
H4A	0.1056	0.5201	0.6883	0.030*
C5	0.08622 (11)	0.39566 (15)	0.58865 (8)	0.0210 (2)
H5A	0.0039	0.3991	0.5597	0.025*
C6	0.14702 (10)	0.31810 (13)	0.55349 (7)	0.0171 (2)
C7	0.08369 (9)	0.24054 (14)	0.47038 (7)	0.0168 (2)
C8	−0.01735 (10)	0.16544 (14)	0.44784 (8)	0.0204 (2)
H8A	−0.0494	0.1678	0.4846	0.025*
C9	−0.08255 (10)	0.07754 (15)	0.36700 (8)	0.0238 (3)
H9A	−0.1500	0.1351	0.3266	0.029*
H9B	−0.1121	−0.0149	0.3784	0.029*
C10	−0.00165 (11)	0.04137 (15)	0.32905 (8)	0.0238 (3)
H10A	0.0564	−0.0330	0.3636	0.029*
H10B	−0.0479	0.0007	0.2725	0.029*
C11	0.06081 (11)	0.18384 (15)	0.32531 (8)	0.0215 (2)
H11A	0.0021	0.2586	0.2922	0.026*
H11B	0.1076	0.1627	0.2972	0.026*
C12	0.14166 (10)	0.24639 (14)	0.41394 (7)	0.0170 (2)
H12A	0.2152	0.1882	0.4402	0.020*
C13	0.25958 (9)	0.42884 (13)	0.39558 (7)	0.0165 (2)
C14	0.43819 (12)	0.44070 (16)	0.36673 (10)	0.0288 (3)
H14A	0.5217	0.4477	0.4074	0.035*
H14B	0.4309	0.4142	0.3121	0.035*
C15	0.37776 (10)	0.58888 (15)	0.36075 (8)	0.0212 (2)
C16	0.21796 (10)	0.70455 (14)	0.38096 (7)	0.0183 (2)
H16A	0.1399	0.6726	0.3705	0.022*
H16B	0.2079	0.7734	0.3362	0.022*
C17	0.27962 (9)	0.78435 (13)	0.46541 (7)	0.0172 (2)
C18	0.34360 (10)	0.91455 (14)	0.47333 (8)	0.0197 (2)
H18A	0.3475	0.9524	0.4265	0.024*
C19	0.40185 (10)	0.98879 (15)	0.55063 (8)	0.0226 (2)
H19A	0.4447	1.0756	0.5555	0.027*
C20	0.39554 (11)	0.93244 (16)	0.62022 (8)	0.0248 (3)
H20A	0.4332	0.9827	0.6717	0.030*
C21	0.33340 (11)	0.80141 (16)	0.61358 (8)	0.0249 (3)
H21A	0.3307	0.7632	0.6608	0.030*
C22	0.27519 (10)	0.72727 (15)	0.53625 (8)	0.0208 (2)
H22A	0.2333	0.6397	0.5317	0.025*

	U11	U22	U33	U12	U13	U23
S1	0.02555 (14)	0.01899 (15)	0.03463 (18)	0.00580 (11)	0.01988 (13)	0.00295 (13)
O1	0.0295 (4)	0.0247 (5)	0.0331 (5)	−0.0013 (4)	0.0198 (4)	0.0046 (4)
N1	0.0181 (4)	0.0166 (5)	0.0159 (4)	0.0006 (3)	0.0083 (3)	−0.0002 (4)
N2	0.0179 (4)	0.0166 (5)	0.0192 (5)	0.0021 (3)	0.0101 (3)	0.0010 (4)
C1	0.0202 (5)	0.0209 (6)	0.0193 (5)	0.0006 (4)	0.0093 (4)	−0.0007 (5)
C2	0.0244 (5)	0.0275 (7)	0.0197 (6)	−0.0027 (5)	0.0086 (4)	−0.0002 (5)
C3	0.0366 (7)	0.0245 (7)	0.0168 (6)	−0.0034 (5)	0.0127 (5)	−0.0021 (5)
C4	0.0372 (7)	0.0233 (6)	0.0209 (6)	0.0042 (5)	0.0188 (5)	0.0016 (5)
C5	0.0232 (5)	0.0214 (6)	0.0209 (6)	0.0035 (4)	0.0126 (4)	0.0038 (5)
C6	0.0191 (5)	0.0165 (5)	0.0166 (5)	0.0010 (4)	0.0093 (4)	0.0022 (4)
C7	0.0173 (4)	0.0163 (5)	0.0166 (5)	0.0020 (4)	0.0079 (4)	0.0014 (4)
C8	0.0196 (5)	0.0208 (6)	0.0205 (6)	0.0004 (4)	0.0091 (4)	0.0020 (5)
C9	0.0208 (5)	0.0223 (6)	0.0243 (6)	−0.0032 (4)	0.0075 (4)	0.0001 (5)
C10	0.0241 (5)	0.0188 (6)	0.0233 (6)	−0.0003 (4)	0.0070 (4)	−0.0040 (5)
C11	0.0241 (5)	0.0217 (6)	0.0191 (6)	−0.0011 (4)	0.0105 (4)	−0.0033 (5)
C12	0.0178 (4)	0.0157 (5)	0.0181 (5)	0.0009 (4)	0.0090 (4)	−0.0004 (4)
C13	0.0184 (4)	0.0161 (5)	0.0149 (5)	0.0025 (4)	0.0078 (4)	0.0001 (4)
C14	0.0308 (6)	0.0245 (7)	0.0426 (8)	0.0042 (5)	0.0269 (6)	0.0031 (6)
C15	0.0208 (5)	0.0246 (6)	0.0207 (6)	0.0012 (4)	0.0118 (4)	0.0007 (5)
C16	0.0168 (4)	0.0169 (5)	0.0190 (5)	0.0029 (4)	0.0069 (4)	0.0012 (4)
C17	0.0146 (4)	0.0164 (5)	0.0197 (5)	0.0034 (4)	0.0076 (4)	0.0007 (4)
C18	0.0198 (5)	0.0166 (6)	0.0226 (6)	0.0021 (4)	0.0101 (4)	0.0017 (4)
C19	0.0186 (5)	0.0181 (6)	0.0279 (6)	0.0007 (4)	0.0084 (4)	−0.0023 (5)
C20	0.0231 (5)	0.0249 (7)	0.0204 (6)	0.0067 (5)	0.0055 (4)	−0.0032 (5)
C21	0.0279 (6)	0.0257 (7)	0.0215 (6)	0.0073 (5)	0.0122 (5)	0.0034 (5)
C22	0.0208 (5)	0.0197 (6)	0.0234 (6)	0.0023 (4)	0.0118 (4)	0.0014 (5)

S1—C13	1.7762 (12)	C9—H9B	0.9700
S1—C14	1.8054 (14)	C10—C11	1.5220 (18)
O1—C15	1.2153 (16)	C10—H10A	0.9700
N1—C13	1.2660 (15)	C10—H10B	0.9700
N1—C12	1.4724 (16)	C11—C12	1.5323 (16)
N2—C15	1.3742 (15)	C11—H11A	0.9700
N2—C13	1.4020 (16)	C11—H11B	0.9700
N2—C16	1.4691 (15)	C12—H12A	0.9800
C1—C2	1.3872 (17)	C14—C15	1.5112 (18)
C1—C6	1.4033 (16)	C14—H14A	0.9700
C1—H1A	0.9300	C14—H14B	0.9700
C2—C3	1.388 (2)	C16—C17	1.5133 (17)
C2—H2A	0.9300	C16—H16A	0.9700
C3—C4	1.3900 (19)	C16—H16B	0.9700
C3—H3A	0.9300	C17—C18	1.3909 (17)
C4—C5	1.3888 (18)	C17—C22	1.3968 (18)
C4—H4A	0.9300	C18—C19	1.3915 (18)
C5—C6	1.3992 (17)	C18—H18A	0.9300
C5—H5A	0.9300	C19—C20	1.385 (2)
C6—C7	1.4873 (16)	C19—H19A	0.9300
C7—C8	1.3401 (16)	C20—C21	1.389 (2)
C7—C12	1.5178 (17)	C20—H20A	0.9300
C8—C9	1.5053 (18)	C21—C22	1.3915 (18)
C8—H8A	0.9300	C21—H21A	0.9300
C9—C10	1.5241 (19)	C22—H22A	0.9300
C9—H9A	0.9700
C13—S1—C14	92.31 (6)	C12—C11—H11B	109.3
C13—N1—C12	118.15 (10)	H11A—C11—H11B	108.0
C15—N2—C13	117.62 (10)	N1—C12—C7	109.12 (10)
C15—N2—C16	120.86 (10)	N1—C12—C11	108.27 (10)
C13—N2—C16	121.51 (9)	C7—C12—C11	112.11 (9)
C2—C1—C6	121.02 (12)	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
C1—C2—C3	120.45 (12)	N1—C13—N2	121.50 (10)
C1—C2—H2A	119.8	N1—C13—S1	128.48 (10)
C3—C2—H2A	119.8	N2—C13—S1	110.02 (8)
C2—C3—C4	119.12 (12)	C15—C14—S1	108.11 (9)
C2—C3—H3A	120.4	C15—C14—H14A	110.1
C4—C3—H3A	120.4	S1—C14—H14A	110.1
C5—C4—C3	120.67 (12)	C15—C14—H14B	110.1
C5—C4—H4A	119.7	S1—C14—H14B	110.1
C3—C4—H4A	119.7	H14A—C14—H14B	108.4
C4—C5—C6	120.79 (11)	O1—C15—N2	124.27 (12)
C4—C5—H5A	119.6	O1—C15—C14	124.27 (11)
C6—C5—H5A	119.6	N2—C15—C14	111.46 (11)
C5—C6—C1	117.92 (11)	N2—C16—C17	111.40 (9)
C5—C6—C7	121.86 (10)	N2—C16—H16A	109.3
C1—C6—C7	120.22 (11)	C17—C16—H16A	109.3
C8—C7—C6	121.55 (11)	N2—C16—H16B	109.3
C8—C7—C12	121.86 (11)	C17—C16—H16B	109.3
C6—C7—C12	116.55 (10)	H16A—C16—H16B	108.0
C7—C8—C9	124.42 (12)	C18—C17—C22	119.36 (11)
C7—C8—H8A	117.8	C18—C17—C16	119.80 (11)
C9—C8—H8A	117.8	C22—C17—C16	120.83 (11)
C8—C9—C10	110.96 (10)	C17—C18—C19	120.68 (12)
C8—C9—H9A	109.4	C17—C18—H18A	119.7
C10—C9—H9A	109.4	C19—C18—H18A	119.7
C8—C9—H9B	109.4	C20—C19—C18	119.52 (12)
C10—C9—H9B	109.4	C20—C19—H19A	120.2
H9A—C9—H9B	108.0	C18—C19—H19A	120.2
C11—C10—C9	109.18 (11)	C19—C20—C21	120.45 (12)
C11—C10—H10A	109.8	C19—C20—H20A	119.8
C9—C10—H10A	109.8	C21—C20—H20A	119.8
C11—C10—H10B	109.8	C20—C21—C22	119.96 (13)
C9—C10—H10B	109.8	C20—C21—H21A	120.0
H10A—C10—H10B	108.3	C22—C21—H21A	120.0
C10—C11—C12	111.64 (10)	C21—C22—C17	120.02 (12)
C10—C11—H11A	109.3	C21—C22—H22A	120.0
C12—C11—H11A	109.3	C17—C22—H22A	120.0
C10—C11—H11B	109.3
C6—C1—C2—C3	−1.9 (2)	C12—N1—C13—S1	−5.83 (16)
C1—C2—C3—C4	1.0 (2)	C15—N2—C13—N1	−173.23 (11)
C2—C3—C4—C5	0.6 (2)	C16—N2—C13—N1	6.54 (17)
C3—C4—C5—C6	−1.2 (2)	C15—N2—C13—S1	6.76 (13)
C4—C5—C6—C1	0.25 (19)	C16—N2—C13—S1	−173.47 (8)
C4—C5—C6—C7	−179.85 (12)	C14—S1—C13—N1	173.49 (12)
C2—C1—C6—C5	1.27 (19)	C14—S1—C13—N2	−6.49 (9)
C2—C1—C6—C7	−178.63 (12)	C13—S1—C14—C15	4.84 (10)
C5—C6—C7—C8	−39.26 (18)	C13—N2—C15—O1	176.88 (12)
C1—C6—C7—C8	140.65 (13)	C16—N2—C15—O1	−2.89 (18)
C5—C6—C7—C12	142.81 (12)	C13—N2—C15—C14	−3.02 (15)
C1—C6—C7—C12	−37.29 (16)	C16—N2—C15—C14	177.21 (11)
C6—C7—C8—C9	−176.52 (11)	S1—C14—C15—O1	178.04 (11)
C12—C7—C8—C9	1.30 (19)	S1—C14—C15—N2	−2.07 (14)
C7—C8—C9—C10	18.81 (18)	C15—N2—C16—C17	−83.38 (13)
C8—C9—C10—C11	−49.49 (14)	C13—N2—C16—C17	96.86 (12)
C9—C10—C11—C12	63.30 (13)	N2—C16—C17—C18	101.26 (12)
C13—N1—C12—C7	148.59 (10)	N2—C16—C17—C22	−77.43 (13)
C13—N1—C12—C11	−89.14 (12)	C22—C17—C18—C19	−0.68 (17)
C8—C7—C12—N1	130.49 (12)	C16—C17—C18—C19	−179.39 (10)
C6—C7—C12—N1	−51.58 (13)	C17—C18—C19—C20	−0.22 (18)
C8—C7—C12—C11	10.56 (16)	C18—C19—C20—C21	1.14 (18)
C6—C7—C12—C11	−171.51 (10)	C19—C20—C21—C22	−1.14 (18)
C10—C11—C12—N1	−163.06 (10)	C20—C21—C22—C17	0.22 (18)
C10—C11—C12—C7	−42.63 (14)	C18—C17—C22—C21	0.68 (17)
C12—N1—C13—N2	174.16 (10)	C16—C17—C22—C21	179.37 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Cg1	0.93	2.97	3.7662 (15)	143

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯Cg1	0.93	2.97	3.7662 (15)	143