2-(4-Chloro-phen-yl)-N-(1,3-thia-zol-2-yl)acetamide.

In the title compound, C(11)H(9)ClN(2)OS, the thia-zole ring is nearly planar (r.m.s. deviation = 0.003 Å) and forms a dihedral angle of 64.18 (7)° with the bezene ring. In the crystal, inversion dimers linked by pairs of N-H⋯N(t) (t = thia-zole) hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ▶,b ▶, 2012a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H9ClN2OS

M = 252.71

Monoclinic,

a = 13.9169 (13) Å

b = 5.5188 (5) Å

c = 15.1836 (14) Å

β = 100.311 (2)°

V = 1147.34 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 296 K

0.35 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.847, T max = 0.918

11463 measured reflections

3421 independent reflections

2769 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.116

S = 1.02

3421 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 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/S1600536812034629/hb6927sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034629/hb6927Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034629/hb6927Isup3.cml

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

C11H9ClN2OS	F(000) = 520
Mr = 252.71	Dx = 1.463 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4547 reflections
a = 13.9169 (13) Å	θ = 2.7–30.3°
b = 5.5188 (5) Å	µ = 0.49 mm−1
c = 15.1836 (14) Å	T = 296 K
β = 100.311 (2)°	Block, orange
V = 1147.34 (18) Å3	0.35 × 0.29 × 0.18 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	3421 independent reflections
Radiation source: fine-focus sealed tube	2769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 30.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.847, Tmax = 0.918	k = −7→7
11463 measured reflections	l = −21→21

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.2113P] where P = (Fo2 + 2Fc2)/3
3421 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.20822 (3)	0.54220 (12)	0.82496 (4)	0.08193 (19)
S1	0.39710 (3)	1.03306 (7)	1.11917 (3)	0.04855 (13)
O1	0.23806 (7)	0.8565 (2)	1.00294 (8)	0.0547 (3)
N1	0.53067 (8)	0.7454 (2)	1.08411 (8)	0.0444 (3)
N2	0.37558 (8)	0.6335 (2)	1.00962 (8)	0.0410 (2)
C1	0.51611 (12)	1.0855 (3)	1.16882 (11)	0.0530 (4)
H1A	0.5365	1.2115	1.2085	0.064*
C2	0.57568 (11)	0.9199 (3)	1.14263 (11)	0.0503 (3)
H2A	0.6429	0.9223	1.1626	0.060*
C3	0.43688 (9)	0.7846 (2)	1.06618 (8)	0.0370 (3)
C4	0.27847 (9)	0.6768 (2)	0.98005 (9)	0.0409 (3)
C5	0.22953 (11)	0.4817 (3)	0.91743 (12)	0.0508 (4)
H5A	0.2547	0.4902	0.8619	0.061*
H5B	0.2473	0.3248	0.9442	0.061*
C6	0.11993 (10)	0.4988 (2)	0.89603 (9)	0.0396 (3)
C7	0.06207 (10)	0.3160 (2)	0.92138 (9)	0.0425 (3)
H7A	0.0916	0.1835	0.9531	0.051*
C8	−0.03890 (11)	0.3270 (3)	0.90033 (10)	0.0458 (3)
H8A	−0.0773	0.2037	0.9174	0.055*
C9	−0.08118 (10)	0.5259 (3)	0.85331 (9)	0.0457 (3)
C10	−0.02621 (11)	0.7100 (3)	0.82739 (9)	0.0501 (3)
H10A	−0.0562	0.8422	0.7958	0.060*
C11	0.07454 (11)	0.6961 (3)	0.84901 (9)	0.0465 (3)
H11A	0.1124	0.8204	0.8319	0.056*
H1N2	0.4009 (14)	0.518 (3)	0.9827 (12)	0.052 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0398 (2)	0.1231 (5)	0.0797 (3)	0.0207 (2)	0.0020 (2)	0.0027 (3)
S1	0.0515 (2)	0.03917 (19)	0.0564 (2)	0.00832 (14)	0.01343 (16)	−0.00790 (14)
O1	0.0402 (5)	0.0473 (6)	0.0736 (7)	0.0117 (4)	0.0022 (5)	−0.0138 (5)
N1	0.0366 (5)	0.0441 (6)	0.0521 (6)	0.0018 (5)	0.0068 (5)	−0.0104 (5)
N2	0.0334 (5)	0.0361 (5)	0.0530 (6)	0.0044 (4)	0.0067 (5)	−0.0074 (5)
C1	0.0612 (9)	0.0455 (8)	0.0523 (8)	−0.0065 (7)	0.0099 (7)	−0.0129 (6)
C2	0.0433 (7)	0.0531 (8)	0.0529 (8)	−0.0051 (6)	0.0044 (6)	−0.0103 (6)
C3	0.0374 (6)	0.0328 (6)	0.0418 (6)	0.0036 (5)	0.0098 (5)	−0.0006 (5)
C4	0.0347 (6)	0.0398 (6)	0.0480 (7)	0.0047 (5)	0.0069 (5)	−0.0009 (5)
C5	0.0387 (7)	0.0504 (8)	0.0615 (9)	0.0064 (6)	0.0041 (6)	−0.0147 (7)
C6	0.0377 (6)	0.0405 (6)	0.0388 (6)	0.0062 (5)	0.0016 (5)	−0.0073 (5)
C7	0.0460 (7)	0.0368 (6)	0.0422 (6)	0.0087 (5)	0.0012 (5)	−0.0007 (5)
C8	0.0445 (7)	0.0466 (7)	0.0465 (7)	0.0006 (6)	0.0085 (6)	−0.0025 (6)
C9	0.0369 (6)	0.0582 (8)	0.0395 (6)	0.0115 (6)	0.0003 (5)	−0.0069 (6)
C10	0.0560 (8)	0.0472 (8)	0.0421 (7)	0.0150 (6)	−0.0051 (6)	0.0032 (6)
C11	0.0524 (8)	0.0415 (7)	0.0437 (7)	−0.0003 (6)	0.0033 (6)	0.0019 (5)

Cl1—C9	1.7455 (15)	C5—C6	1.5045 (19)
S1—C1	1.7170 (17)	C5—H5A	0.9700
S1—C3	1.7300 (13)	C5—H5B	0.9700
O1—C4	1.2211 (16)	C6—C7	1.388 (2)
N1—C3	1.3029 (17)	C6—C11	1.3904 (19)
N1—C2	1.3820 (18)	C7—C8	1.386 (2)
N2—C4	1.3666 (16)	C7—H7A	0.9300
N2—C3	1.3778 (17)	C8—C9	1.382 (2)
N2—H1N2	0.868 (19)	C8—H8A	0.9300
C1—C2	1.341 (2)	C9—C10	1.371 (2)
C1—H1A	0.9300	C10—C11	1.384 (2)
C2—H2A	0.9300	C10—H10A	0.9300
C4—C5	1.515 (2)	C11—H11A	0.9300
C1—S1—C3	88.50 (7)	C4—C5—H5B	108.6
C3—N1—C2	109.91 (12)	H5A—C5—H5B	107.6
C4—N2—C3	124.38 (11)	C7—C6—C11	118.63 (13)
C4—N2—H1N2	115.8 (12)	C7—C6—C5	120.71 (13)
C3—N2—H1N2	118.8 (12)	C11—C6—C5	120.65 (14)
C2—C1—S1	110.73 (12)	C8—C7—C6	121.25 (13)
C2—C1—H1A	124.6	C8—C7—H7A	119.4
S1—C1—H1A	124.6	C6—C7—H7A	119.4
C1—C2—N1	115.61 (14)	C9—C8—C7	118.34 (14)
C1—C2—H2A	122.2	C9—C8—H8A	120.8
N1—C2—H2A	122.2	C7—C8—H8A	120.8
N1—C3—N2	121.01 (11)	C10—C9—C8	121.92 (13)
N1—C3—S1	115.24 (10)	C10—C9—Cl1	118.92 (11)
N2—C3—S1	123.75 (10)	C8—C9—Cl1	119.15 (13)
O1—C4—N2	121.81 (13)	C9—C10—C11	118.98 (13)
O1—C4—C5	125.28 (12)	C9—C10—H10A	120.5
N2—C4—C5	112.91 (11)	C11—C10—H10A	120.5
C6—C5—C4	114.56 (11)	C10—C11—C6	120.88 (14)
C6—C5—H5A	108.6	C10—C11—H11A	119.6
C4—C5—H5A	108.6	C6—C11—H11A	119.6
C6—C5—H5B	108.6
C3—S1—C1—C2	0.48 (13)	C4—C5—C6—C7	−116.45 (15)
S1—C1—C2—N1	−0.8 (2)	C4—C5—C6—C11	64.72 (19)
C3—N1—C2—C1	0.7 (2)	C11—C6—C7—C8	0.3 (2)
C2—N1—C3—N2	−179.52 (13)	C5—C6—C7—C8	−178.55 (13)
C2—N1—C3—S1	−0.32 (16)	C6—C7—C8—C9	−0.1 (2)
C4—N2—C3—N1	−172.65 (13)	C7—C8—C9—C10	0.0 (2)
C4—N2—C3—S1	8.23 (19)	C7—C8—C9—Cl1	179.30 (11)
C1—S1—C3—N1	−0.08 (12)	C8—C9—C10—C11	0.0 (2)
C1—S1—C3—N2	179.09 (12)	Cl1—C9—C10—C11	−179.33 (11)
C3—N2—C4—O1	−0.6 (2)	C9—C10—C11—C6	0.2 (2)
C3—N2—C4—C5	179.13 (13)	C7—C6—C11—C10	−0.3 (2)
O1—C4—C5—C6	−10.4 (2)	C5—C6—C11—C10	178.52 (13)
N2—C4—C5—C6	169.89 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1i	0.866 (18)	2.096 (18)	2.9606 (16)	176.2 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1i	0.866 (18)	2.096 (18)	2.9606 (16)	176.2 (17)

Symmetry code: (i) .