(Z)-N-{3-[1-(4-Chloro-phen-yl)eth-yl]thia-zolidin-2-yl-idene}cyanamide.

The title compound, C(12)H(12)ClN(3)S, features a thia-zolyl ring having an envelope conformation with the -CH(2)- group bonded to the S atom forming the flap. The C=N double bond has a Z configuration. The crystal structure shows inter-molecular C-H⋯S hydrogen bonds.

Related literature

For the biological activity of thia­zole componds, see: Hense et al. (2002 ▶). For a related structure, see: Cunico et al. (2007 ▶). For the synthesis, see: Jeschke et al. (2002 ▶).

Experimental

Crystal data

C12H12ClN3S

M = 265.76

Orthorhombic,

a = 5.8850 (12) Å

b = 7.5965 (15) Å

c = 28.273 (6) Å

V = 1264.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 113 K

0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.940, T max = 0.957

9219 measured reflections

3019 independent reflections

2640 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.113

S = 1.06

3019 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 6200 Friedel pairs

Flack parameter: −0.09 (9)

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810029879/ng5002sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029879/ng5002Isup2.hkl

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

C12H12ClN3S	F(000) = 552
Mr = 265.76	Dx = 1.397 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 193 reflections
a = 5.8850 (12) Å	θ = 1.4–27.9°
b = 7.5965 (15) Å	µ = 0.45 mm−1
c = 28.273 (6) Å	T = 113 K
V = 1264.0 (4) Å3	Block, white
Z = 4	0.14 × 0.12 × 0.10 mm

Rigaku Saturn diffractometer	3019 independent reflections
Radiation source: rotating anode	2640 reflections with I > 2σ(I)
confocal	Rint = 0.062
ω scans	θmax = 27.9°, θmin = 1.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −7→7
Tmin = 0.940, Tmax = 0.957	k = −9→8
9219 measured reflections	l = −29→37

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.0295P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3019 reflections	Δρmax = 0.38 e Å−3
155 parameters	Δρmin = −0.34 e Å−3
0 restraints	Absolute structure: Flack (1983), 6200 Friedel pairs
Primary atom site location: structure-invariant direct methods

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	0.31420 (16)	−0.62970 (7)	0.98241 (2)	0.0438 (2)
S1	0.18444 (12)	0.16944 (8)	0.77090 (2)	0.03081 (17)
N2	0.2773 (4)	0.3380 (3)	0.85392 (7)	0.0279 (4)
C9	0.3024 (4)	0.1982 (3)	0.82718 (8)	0.0238 (5)
C1	0.2990 (4)	−0.1331 (3)	0.93777 (8)	0.0267 (5)
H1	0.2024	−0.0368	0.9407	0.032*
N1	0.4250 (4)	0.0594 (2)	0.84129 (6)	0.0255 (5)
C6	0.4992 (4)	−0.1158 (3)	0.91192 (8)	0.0242 (5)
C7	0.5466 (4)	0.0572 (3)	0.88698 (8)	0.0257 (5)
H7	0.4806	0.1507	0.9065	0.031*
C8	0.7950 (5)	0.1029 (4)	0.87970 (9)	0.0369 (6)
H8A	0.8064	0.2125	0.8630	0.055*
H8B	0.8672	0.0117	0.8616	0.055*
H8C	0.8686	0.1135	0.9099	0.055*
C12	0.1462 (5)	0.4672 (3)	0.83801 (8)	0.0294 (6)
C2	0.2409 (4)	−0.2905 (3)	0.95914 (8)	0.0288 (5)
H2	0.1055	−0.3011	0.9759	0.035*
C4	0.5886 (5)	−0.4192 (3)	0.93042 (9)	0.0316 (6)
H4	0.6860	−0.5152	0.9284	0.038*
C3	0.3874 (5)	−0.4315 (3)	0.95515 (8)	0.0285 (5)
N3	0.0347 (5)	0.5868 (3)	0.82737 (8)	0.0414 (6)
C5	0.6432 (5)	−0.2610 (3)	0.90865 (8)	0.0292 (6)
H5	0.7778	−0.2518	0.8916	0.035*
C11	0.4588 (7)	−0.0759 (4)	0.80600 (9)	0.0479 (8)
H11A	0.6166	−0.0769	0.7961	0.058*
H11B	0.4235	−0.1901	0.8195	0.058*
C10	0.3144 (8)	−0.0437 (4)	0.76555 (12)	0.0648 (12)
H10A	0.1977	−0.1336	0.7638	0.078*
H10B	0.4039	−0.0488	0.7368	0.078*

	U11	U22	U33	U12	U13	U23
Cl1	0.0702 (5)	0.0288 (3)	0.0324 (4)	−0.0048 (3)	0.0066 (4)	0.0021 (3)
S1	0.0384 (4)	0.0355 (3)	0.0185 (3)	−0.0011 (3)	−0.0028 (3)	0.0002 (2)
N2	0.0319 (11)	0.0266 (9)	0.0252 (11)	−0.0013 (9)	−0.0015 (9)	−0.0014 (8)
C9	0.0227 (11)	0.0302 (11)	0.0186 (11)	−0.0047 (10)	0.0030 (10)	0.0020 (8)
C1	0.0253 (12)	0.0304 (11)	0.0246 (12)	0.0062 (11)	0.0008 (10)	0.0000 (9)
N1	0.0305 (11)	0.0255 (10)	0.0204 (11)	0.0005 (9)	−0.0029 (9)	−0.0032 (8)
C6	0.0232 (11)	0.0293 (11)	0.0201 (12)	−0.0007 (9)	−0.0038 (9)	−0.0022 (9)
C7	0.0267 (12)	0.0289 (12)	0.0215 (13)	−0.0010 (10)	−0.0029 (10)	−0.0016 (9)
C8	0.0319 (14)	0.0419 (14)	0.0368 (16)	−0.0080 (13)	−0.0029 (12)	0.0067 (12)
C12	0.0371 (15)	0.0332 (12)	0.0179 (12)	−0.0011 (11)	0.0008 (10)	−0.0010 (9)
C2	0.0284 (13)	0.0332 (12)	0.0249 (13)	−0.0021 (10)	0.0014 (10)	−0.0010 (10)
C4	0.0376 (14)	0.0252 (11)	0.0319 (14)	0.0079 (11)	−0.0017 (11)	−0.0064 (10)
C3	0.0386 (14)	0.0260 (11)	0.0210 (13)	−0.0031 (11)	−0.0019 (10)	−0.0016 (10)
N3	0.0575 (17)	0.0394 (12)	0.0273 (13)	0.0087 (12)	−0.0025 (11)	−0.0006 (10)
C5	0.0296 (14)	0.0329 (11)	0.0252 (14)	0.0034 (11)	0.0024 (10)	−0.0026 (10)
C11	0.069 (2)	0.0489 (16)	0.0254 (15)	0.0203 (17)	−0.0048 (14)	−0.0132 (13)
C10	0.097 (3)	0.0508 (18)	0.046 (2)	0.027 (2)	−0.038 (2)	−0.0243 (14)

Cl1—C3	1.746 (2)	C8—H8A	0.9600
S1—C9	1.750 (2)	C8—H8B	0.9600
S1—C10	1.797 (3)	C8—H8C	0.9600
N2—C9	1.311 (3)	C12—N3	1.161 (3)
N2—C12	1.327 (3)	C2—C3	1.380 (4)
C9—N1	1.338 (3)	C2—H2	0.9300
C1—C2	1.383 (3)	C4—C3	1.378 (4)
C1—C6	1.393 (3)	C4—C5	1.388 (3)
C1—H1	0.9300	C4—H4	0.9300
N1—C11	1.446 (3)	C5—H5	0.9300
N1—C7	1.477 (3)	C11—C10	1.446 (4)
C6—C5	1.394 (3)	C11—H11A	0.9700
C6—C7	1.517 (3)	C11—H11B	0.9700
C7—C8	1.516 (4)	C10—H10A	0.9700
C7—H7	0.9800	C10—H10B	0.9700
C9—S1—C10	91.16 (13)	N3—C12—N2	174.7 (3)
C9—N2—C12	118.0 (2)	C3—C2—C1	118.8 (2)
N2—C9—N1	121.8 (2)	C3—C2—H2	120.6
N2—C9—S1	125.49 (18)	C1—C2—H2	120.6
N1—C9—S1	112.73 (17)	C3—C4—C5	118.9 (2)
C2—C1—C6	121.3 (2)	C3—C4—H4	120.6
C2—C1—H1	119.3	C5—C4—H4	120.6
C6—C1—H1	119.3	C4—C3—C2	121.7 (2)
C9—N1—C11	115.4 (2)	C4—C3—Cl1	119.64 (19)
C9—N1—C7	122.06 (19)	C2—C3—Cl1	118.6 (2)
C11—N1—C7	121.9 (2)	C4—C5—C6	121.0 (2)
C1—C6—C5	118.3 (2)	C4—C5—H5	119.5
C1—C6—C7	118.8 (2)	C6—C5—H5	119.5
C5—C6—C7	122.9 (2)	C10—C11—N1	110.1 (2)
N1—C7—C8	110.2 (2)	C10—C11—H11A	109.6
N1—C7—C6	109.10 (19)	N1—C11—H11A	109.6
C8—C7—C6	116.0 (2)	C10—C11—H11B	109.6
N1—C7—H7	107.0	N1—C11—H11B	109.6
C8—C7—H7	107.0	H11A—C11—H11B	108.1
C6—C7—H7	107.0	C11—C10—S1	109.6 (2)
C7—C8—H8A	109.5	C11—C10—H10A	109.7
C7—C8—H8B	109.5	S1—C10—H10A	109.7
H8A—C8—H8B	109.5	C11—C10—H10B	109.7
C7—C8—H8C	109.5	S1—C10—H10B	109.7
H8A—C8—H8C	109.5	H10A—C10—H10B	108.2
H8B—C8—H8C	109.5
C12—N2—C9—N1	−177.6 (2)	C1—C6—C7—C8	152.3 (2)
C12—N2—C9—S1	2.1 (3)	C5—C6—C7—C8	−30.3 (3)
C10—S1—C9—N2	179.1 (3)	C9—N2—C12—N3	177 (100)
C10—S1—C9—N1	−1.1 (2)	C6—C1—C2—C3	1.1 (4)
N2—C9—N1—C11	−173.2 (2)	C5—C4—C3—C2	−0.6 (4)
S1—C9—N1—C11	7.0 (3)	C5—C4—C3—Cl1	179.5 (2)
N2—C9—N1—C7	−2.4 (4)	C1—C2—C3—C4	−0.2 (4)
S1—C9—N1—C7	177.89 (18)	C1—C2—C3—Cl1	179.7 (2)
C2—C1—C6—C5	−1.1 (4)	C3—C4—C5—C6	0.6 (4)
C2—C1—C6—C7	176.5 (2)	C1—C6—C5—C4	0.2 (4)
C9—N1—C7—C8	−98.3 (3)	C7—C6—C5—C4	−177.3 (2)
C11—N1—C7—C8	72.0 (3)	C9—N1—C11—C10	−10.7 (4)
C9—N1—C7—C6	133.2 (2)	C7—N1—C11—C10	178.5 (3)
C11—N1—C7—C6	−56.5 (3)	N1—C11—C10—S1	9.2 (4)
C1—C6—C7—N1	−82.5 (3)	C9—S1—C10—C11	−4.8 (3)
C5—C6—C7—N1	94.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···S1i	0.97	2.87	3.799 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯S1i	0.97	2.87	3.799 (4)	160

Symmetry code: (i) .