N-[(Z)-3-(4-Chloro­benzo­yl)-1,3-thia­zolidin-2-yl­idene]cyanamide

The title compound, C₁₁H₈ClN₃OS, was prepared by the reaction of N-cyano­imino­thia­zolidine, 2-amino­ethanethiol and triethyl­amine at 350 K. The dihedral angle between the two rings is 62.5 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.026
• wR factor = 0.066
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   293.000
            Value of melting point given =     0.000
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     --  C11     ..       6.62 su

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Thiazolidine is an important group in organic chemistry. Many compounds containing thiazolidine groups possess a broad spectrum of biological activities (Iwata et al., 1988; Huang & Shi, 1990).

In the crystal structure (Fig. 1), the torsion angle formed by atoms N1, C8, C9 and S1 was 34.5 (9)°. The dihedral angle formed by the the ring (N1, C8, C9, C10 and S1) and the phenyl ring (C1-C6) was 62.5 (8)°. The C=N bond length (1.299 (2) Å) is in agreement with that observed before (Jian et al., 2006). The C—S bond length (1.734 (7) and 1.808 (2) Å) are in agreement with those observed before (Schroth et al., 1997). Intermolecular C–H···N interactions help to stabilize the crystal structure.

Related literature

For the biological activities of thiazolidine compounds, see: Iwata et al. (1988); Huang & Shi (1990). For related structures, see Jian et al. (2006); Schroth et al. (1997).

S2. Experimental

A mixture of N-cyanoiminothiazolidine 10 mmol (1.27 g), 2-amino-ethanethiol (1.75 g, 10 mmol) and (1.01 g, 10 mmol) triethylamine was refluxed in absolute acetone (25 ml) for 4 h. On cooling, the product crystallized, was filtered, and recrystallized from absolute EtOH (yield 2.42 g (91%)). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

S3. Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, respectively, and U_iso(H) = 1.2 U_eq of the parent atoms.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level.

N-[(Z)-3-(4-Chlorobenzoyl)-1,3-thiazolidin-2-ylidene]cyanamide

Crystal data

C11H8ClN3OS	F(000) = 544
Mr = 265.72	Dx = 1.539 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1021 reflections
a = 16.442 (3) Å	θ = 2.9–26.4°
b = 5.6798 (11) Å	µ = 0.50 mm^−1
c = 13.313 (3) Å	T = 293 K
β = 112.76 (3)°	Block, colorless
V = 1146.5 (5) Å^3	0.34 × 0.21 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1915 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 3.1°
ϕ and ω scans	h = −19→19
8343 measured reflections	k = −6→6
2016 independent reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.017P)^2 + 0.7287P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
2016 reflections	Δρmax = 0.21 e Å^−3
155 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.07965 (3)	0.52934 (7)	0.33331 (3)	0.02469 (14)
Cl1	0.46689 (3)	0.71315 (8)	0.06338 (3)	0.03512 (15)
O1	0.27367 (8)	1.17756 (19)	0.37317 (10)	0.0302 (3)
N2	0.16368 (9)	0.5912 (2)	0.19639 (11)	0.0244 (3)
C3	0.40564 (10)	0.7898 (3)	0.13961 (12)	0.0229 (3)
N1	0.20390 (8)	0.8283 (2)	0.35254 (10)	0.0216 (3)
C10	0.15500 (10)	0.6503 (3)	0.28595 (12)	0.0201 (3)
C4	0.40148 (10)	0.6326 (3)	0.21690 (12)	0.0232 (3)
H4A	0.4315	0.4901	0.2281	0.028*
N3	0.08333 (10)	0.2509 (3)	0.08619 (14)	0.0426 (4)
C7	0.26182 (10)	0.9843 (3)	0.33103 (12)	0.0220 (3)
C6	0.30963 (9)	0.9060 (3)	0.26219 (12)	0.0197 (3)
C8	0.16984 (11)	0.9017 (3)	0.43566 (13)	0.0263 (4)
H8A	0.1270	1.0272	0.4077	0.032*
H8B	0.2176	0.9574	0.5007	0.032*
C1	0.31667 (10)	1.0641 (3)	0.18625 (13)	0.0227 (3)
H1A	0.2896	1.2106	0.1779	0.027*
C9	0.12728 (11)	0.6865 (3)	0.46101 (13)	0.0268 (4)
H9A	0.0820	0.7312	0.4872	0.032*
H9B	0.1708	0.5901	0.5158	0.032*
C11	0.11795 (11)	0.4075 (3)	0.14112 (14)	0.0275 (4)
C5	0.35225 (10)	0.6895 (3)	0.27740 (12)	0.0222 (3)
H5A	0.3477	0.5833	0.3281	0.027*
C2	0.36370 (10)	1.0057 (3)	0.12284 (13)	0.0244 (3)
H2B	0.3669	1.1093	0.0704	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0224 (2)	0.0236 (2)	0.0314 (2)	−0.00304 (16)	0.01415 (17)	0.00002 (16)
Cl1	0.0368 (3)	0.0412 (3)	0.0340 (2)	0.00200 (19)	0.02096 (19)	−0.00607 (19)
O1	0.0369 (7)	0.0210 (6)	0.0374 (7)	−0.0065 (5)	0.0194 (5)	−0.0072 (5)
N2	0.0252 (7)	0.0244 (7)	0.0252 (7)	−0.0060 (6)	0.0115 (6)	−0.0039 (6)
C3	0.0187 (7)	0.0266 (8)	0.0226 (8)	−0.0038 (6)	0.0071 (6)	−0.0060 (6)
N1	0.0246 (7)	0.0207 (7)	0.0217 (6)	−0.0036 (5)	0.0114 (5)	−0.0012 (5)
C10	0.0185 (7)	0.0167 (7)	0.0243 (8)	0.0018 (6)	0.0075 (6)	0.0039 (6)
C4	0.0194 (8)	0.0190 (7)	0.0273 (8)	0.0006 (6)	0.0047 (6)	−0.0016 (6)
N3	0.0337 (8)	0.0427 (10)	0.0586 (11)	−0.0120 (8)	0.0257 (8)	−0.0256 (9)
C7	0.0218 (8)	0.0201 (8)	0.0229 (8)	−0.0012 (6)	0.0072 (6)	0.0024 (6)
C6	0.0171 (7)	0.0187 (7)	0.0219 (7)	−0.0047 (6)	0.0062 (6)	−0.0019 (6)
C8	0.0293 (8)	0.0284 (8)	0.0244 (8)	−0.0013 (7)	0.0140 (7)	−0.0026 (7)
C1	0.0209 (8)	0.0171 (7)	0.0289 (8)	−0.0013 (6)	0.0082 (6)	0.0017 (6)
C9	0.0248 (8)	0.0326 (9)	0.0236 (8)	−0.0002 (7)	0.0101 (7)	0.0028 (7)
C11	0.0230 (8)	0.0303 (9)	0.0348 (9)	−0.0025 (7)	0.0172 (7)	−0.0056 (8)
C5	0.0226 (8)	0.0192 (8)	0.0227 (8)	−0.0029 (6)	0.0064 (6)	0.0022 (6)
C2	0.0242 (8)	0.0248 (8)	0.0245 (8)	−0.0030 (7)	0.0099 (6)	0.0040 (7)

Geometric parameters (Å, º)

S1—C10	1.7347 (15)	N3—C11	1.152 (2)
S1—C9	1.8082 (17)	C7—C6	1.488 (2)
Cl1—C3	1.7390 (16)	C6—C1	1.390 (2)
O1—C7	1.2136 (19)	C6—C5	1.391 (2)
N2—C10	1.299 (2)	C8—C9	1.510 (2)
N2—C11	1.329 (2)	C8—H8A	0.9700
C3—C2	1.382 (2)	C8—H8B	0.9700
C3—C4	1.384 (2)	C1—C2	1.388 (2)
N1—C10	1.379 (2)	C1—H1A	0.9300
N1—C7	1.409 (2)	C9—H9A	0.9700
N1—C8	1.4804 (19)	C9—H9B	0.9700
C4—C5	1.383 (2)	C5—H5A	0.9300
C4—H4A	0.9300	C2—H2B	0.9300
C10—S1—C9	92.05 (8)	N1—C8—H8A	110.5
C10—N2—C11	118.14 (14)	C9—C8—H8A	110.5
C2—C3—C4	121.83 (14)	N1—C8—H8B	110.5
C2—C3—Cl1	119.55 (12)	C9—C8—H8B	110.5
C4—C3—Cl1	118.61 (12)	H8A—C8—H8B	108.7
C10—N1—C7	127.01 (13)	C2—C1—C6	120.72 (14)
C10—N1—C8	113.06 (12)	C2—C1—H1A	119.6
C7—N1—C8	117.11 (13)	C6—C1—H1A	119.6
N2—C10—N1	122.40 (14)	C8—C9—S1	105.01 (11)
N2—C10—S1	125.37 (12)	C8—C9—H9A	110.7
N1—C10—S1	112.17 (11)	S1—C9—H9A	110.7
C5—C4—C3	119.40 (14)	C8—C9—H9B	110.7
C5—C4—H4A	120.3	S1—C9—H9B	110.7
C3—C4—H4A	120.3	H9A—C9—H9B	108.8
O1—C7—N1	118.36 (14)	N3—C11—N2	172.67 (18)
O1—C7—C6	121.78 (14)	C4—C5—C6	119.80 (14)
N1—C7—C6	119.80 (13)	C4—C5—H5A	120.1
C1—C6—C5	119.87 (14)	C6—C5—H5A	120.1
C1—C6—C7	117.87 (14)	C3—C2—C1	118.32 (14)
C5—C6—C7	122.08 (14)	C3—C2—H2B	120.8
N1—C8—C9	106.32 (13)	C1—C2—H2B	120.8
C11—N2—C10—N1	175.68 (14)	N1—C7—C6—C1	138.53 (15)
C11—N2—C10—S1	−7.2 (2)	O1—C7—C6—C5	130.83 (17)
C7—N1—C10—N2	6.7 (2)	N1—C7—C6—C5	−46.3 (2)
C8—N1—C10—N2	167.01 (14)	C10—N1—C8—C9	29.96 (17)
C7—N1—C10—S1	−170.72 (12)	C7—N1—C8—C9	−167.65 (13)
C8—N1—C10—S1	−10.44 (16)	C5—C6—C1—C2	1.9 (2)
C9—S1—C10—N2	172.92 (14)	C7—C6—C1—C2	177.18 (14)
C9—S1—C10—N1	−9.73 (12)	N1—C8—C9—S1	−34.60 (15)
C2—C3—C4—C5	1.7 (2)	C10—S1—C9—C8	25.81 (12)
Cl1—C3—C4—C5	−179.26 (11)	C3—C4—C5—C6	−1.8 (2)
C10—N1—C7—O1	152.51 (15)	C1—C6—C5—C4	0.0 (2)
C8—N1—C7—O1	−7.1 (2)	C7—C6—C5—C4	−175.00 (14)
C10—N1—C7—C6	−30.2 (2)	C4—C3—C2—C1	0.2 (2)
C8—N1—C7—C6	170.18 (13)	Cl1—C3—C2—C1	−178.80 (12)
O1—C7—C6—C1	−44.3 (2)	C6—C1—C2—C3	−2.1 (2)