N-(4-Bromo-phen-yl)-2-(2-thien-yl)acetamide.

The thienyl ring in the title compound, C(12)H(10)BrNOS, is disordered over two diagonally opposite positions, the major component having a site-occupancy factor of 0.660 (5). The mol-ecule is twisted as evidenced by the dihedral angles of 70.0 (4) and 70.5 (6)° formed between the benzene ring and the two orientations of the disordered thio-phene ring. Linear supra-molecular chains along the a axis are found in the crystal structure through the agency of N-H⋯O hydrogen bonding.

Related literature

For background to the various applications of 2-substituted thio­phenes, see: Campaigne (1984 ▶); Kleemann et al. (2006 ▶). For recent biological studies on 2-substituted thio­phenes, see: Lourenço et al. (2007 ▶). For the structure of the N-(2,6-dimethyl­phen­yl) derivative, see: Ferreira et al. (2009 ▶).

Experimental

Crystal data

C12H10BrNOS

M = 296.18

Triclinic,

a = 4.7517 (2) Å

b = 10.7283 (3) Å

c = 11.7964 (3) Å

α = 76.419 (2)°

β = 88.437 (2)°

γ = 84.479 (2)°

V = 581.82 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.69 mm−1

T = 120 K

0.09 × 0.06 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.845, T max = 1.000

9757 measured reflections

2045 independent reflections

1847 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.115

S = 0.98

2045 reflections

161 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053355/hg2617sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053355/hg2617Isup2.hkl

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

C12H10BrNOS	Z = 2
Mr = 296.18	F(000) = 296
Triclinic, P1	Dx = 1.691 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7517 (2) Å	Cell parameters from 2592 reflections
b = 10.7283 (3) Å	θ = 2.9–27.5°
c = 11.7964 (3) Å	µ = 3.69 mm−1
α = 76.419 (2)°	T = 120 K
β = 88.437 (2)°	Block, pale-brown
γ = 84.479 (2)°	0.09 × 0.06 × 0.02 mm
V = 581.82 (3) Å3

Enraf–Nonius KappaCCD area-detector diffractometer	2045 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1847 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.042
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 2.9°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −12→12
Tmin = 0.845, Tmax = 1.000	l = −14→14
9757 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2045 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 0.40 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
Br	0.27885 (7)	−0.23040 (3)	0.97460 (3)	0.03386 (19)
O1	0.0821 (5)	0.2338 (2)	0.4702 (2)	0.0338 (6)
N1	0.5204 (5)	0.1924 (3)	0.5506 (2)	0.0237 (6)
H1N	0.696 (3)	0.211 (3)	0.540 (3)	0.028*
S1	0.0537 (8)	0.5801 (3)	0.3373 (3)	0.0278 (6)	0.660 (5)
C1	0.2232 (6)	0.4487 (3)	0.3020 (3)	0.0249 (7)	0.660 (5)
C2	−0.1461 (8)	0.6162 (4)	0.2202 (3)	0.0361 (8)	0.660 (5)
H2	−0.2806	0.6894	0.2040	0.043*	0.660 (5)
C3	−0.1056 (7)	0.5346 (4)	0.1488 (3)	0.0318 (8)	0.660 (5)
H3	−0.2006	0.5420	0.0774	0.038*	0.660 (5)
C4	0.108 (4)	0.4342 (19)	0.2003 (15)	0.035 (4)	0.660 (5)
H4	0.1644	0.3633	0.1668	0.042*	0.660 (5)
S1'	0.1360 (17)	0.4123 (9)	0.1850 (6)	0.0245 (14)	0.340 (5)
C1'	0.2232 (6)	0.4487 (3)	0.3020 (3)	0.0249 (7)	0.340 (5)
C2'	−0.1461 (8)	0.6162 (4)	0.2202 (3)	0.0361 (8)	0.340 (5)
H2'	−0.2772	0.6904	0.2108	0.043*	0.340 (5)
C3'	−0.1056 (7)	0.5346 (4)	0.1488 (3)	0.0318 (8)	0.340 (5)
H3'	−0.2134	0.5474	0.0797	0.038*	0.340 (5)
C4'	0.072 (7)	0.561 (3)	0.323 (3)	0.035 (4)	0.340 (5)
H4'	0.0977	0.5980	0.3879	0.042*	0.340 (5)
C5	0.4454 (7)	0.3645 (4)	0.3784 (3)	0.0351 (8)
H5A	0.5485	0.4183	0.4176	0.042*
H5B	0.5828	0.3256	0.3290	0.042*
C6	0.3296 (6)	0.2578 (3)	0.4702 (3)	0.0251 (7)
C7	0.4675 (6)	0.0909 (3)	0.6462 (3)	0.0227 (7)
C8	0.2767 (7)	0.0013 (3)	0.6398 (3)	0.0251 (7)
H8	0.1806	0.0071	0.5689	0.030*
C9	0.2278 (7)	−0.0953 (3)	0.7360 (3)	0.0266 (7)
H9	0.0995	−0.1566	0.7315	0.032*
C10	0.3667 (7)	−0.1026 (3)	0.8397 (3)	0.0252 (7)
C11	0.5612 (7)	−0.0172 (3)	0.8476 (3)	0.0279 (7)
H11	0.6607	−0.0254	0.9181	0.033*
C12	0.6090 (7)	0.0808 (3)	0.7505 (3)	0.0255 (7)
H12	0.7389	0.1414	0.7553	0.031*

	U11	U22	U33	U12	U13	U23
Br	0.0441 (3)	0.0281 (3)	0.0269 (3)	−0.00963 (17)	0.00026 (16)	0.00104 (16)
O1	0.0170 (11)	0.0346 (14)	0.0425 (15)	−0.0075 (10)	−0.0019 (10)	0.0076 (11)
N1	0.0165 (12)	0.0273 (15)	0.0256 (13)	−0.0067 (11)	0.0018 (11)	−0.0008 (11)
S1	0.0324 (10)	0.0221 (11)	0.0298 (12)	−0.0051 (8)	0.0006 (8)	−0.0068 (9)
C1	0.0191 (15)	0.0207 (17)	0.0320 (18)	−0.0039 (12)	0.0043 (13)	−0.0002 (13)
C2	0.0328 (18)	0.0267 (19)	0.042 (2)	−0.0012 (15)	0.0071 (15)	0.0040 (15)
C3	0.0289 (17)	0.039 (2)	0.0236 (17)	−0.0084 (15)	−0.0003 (13)	0.0034 (15)
C4	0.037 (5)	0.038 (7)	0.036 (6)	−0.007 (4)	0.015 (3)	−0.022 (4)
S1'	0.027 (2)	0.029 (3)	0.019 (2)	−0.0057 (17)	0.0037 (17)	−0.007 (2)
C1'	0.0191 (15)	0.0207 (17)	0.0320 (18)	−0.0039 (12)	0.0043 (13)	−0.0002 (13)
C2'	0.0328 (18)	0.0267 (19)	0.042 (2)	−0.0012 (15)	0.0071 (15)	0.0040 (15)
C3'	0.0289 (17)	0.039 (2)	0.0236 (17)	−0.0084 (15)	−0.0003 (13)	0.0034 (15)
C4'	0.037 (5)	0.038 (7)	0.036 (6)	−0.007 (4)	0.015 (3)	−0.022 (4)
C5	0.0228 (16)	0.034 (2)	0.041 (2)	−0.0067 (14)	0.0030 (14)	0.0078 (16)
C6	0.0191 (15)	0.0229 (18)	0.0329 (19)	−0.0039 (13)	0.0040 (13)	−0.0053 (15)
C7	0.0141 (13)	0.0267 (17)	0.0264 (16)	−0.0020 (12)	0.0051 (12)	−0.0050 (13)
C8	0.0278 (16)	0.0224 (17)	0.0257 (16)	−0.0059 (13)	−0.0032 (13)	−0.0048 (13)
C9	0.0254 (16)	0.0235 (17)	0.0317 (17)	−0.0058 (13)	0.0017 (13)	−0.0070 (14)
C10	0.0265 (16)	0.0225 (17)	0.0245 (16)	−0.0022 (13)	0.0025 (13)	−0.0017 (13)
C11	0.0263 (16)	0.0309 (19)	0.0274 (17)	−0.0025 (14)	−0.0008 (13)	−0.0086 (14)
C12	0.0185 (14)	0.0278 (18)	0.0318 (17)	−0.0061 (12)	0.0001 (12)	−0.0087 (14)

Br—C10	1.907 (3)	C2'—C3'	1.348 (5)
O1—C6	1.228 (4)	C2'—C4'	1.59 (3)
N1—C6	1.352 (4)	C2'—H2'	0.9500
N1—C7	1.407 (4)	C3'—H3'	0.9500
N1—H1N	0.875 (10)	C4'—H4'	0.9500
S1—C2	1.647 (5)	C5—C6	1.514 (5)
S1—C1	1.687 (4)	C5—H5A	0.9900
C1—C4	1.381 (17)	C5—H5B	0.9900
C1—C5	1.493 (5)	C7—C12	1.396 (4)
C2—C3	1.348 (5)	C7—C8	1.399 (4)
C2—H2	0.9500	C8—C9	1.377 (5)
C3—C4	1.439 (19)	C8—H8	0.9500
C3—H3	0.9500	C9—C10	1.388 (5)
C4—H4	0.9500	C9—H9	0.9500
S1'—C1'	1.594 (8)	C10—C11	1.382 (5)
S1'—C3'	1.641 (9)	C11—C12	1.391 (5)
C1'—C4'	1.42 (3)	C11—H11	0.9500
C1'—C5	1.493 (5)	C12—H12	0.9500
C6—N1—C7	126.1 (3)	C1—C5—C6	113.6 (3)
C6—N1—H1n	117 (2)	C1'—C5—H5A	108.8
C7—N1—H1n	117 (2)	C1—C5—H5A	108.8
C2—S1—C1	93.6 (2)	C6—C5—H5A	108.8
C4—C1—C5	129.6 (8)	C1'—C5—H5B	108.8
C4—C1—S1	108.3 (8)	C1—C5—H5B	108.8
C5—C1—S1	122.0 (3)	C6—C5—H5B	108.8
C3—C2—S1	115.4 (3)	H5A—C5—H5B	107.7
C3—C2—H2	122.3	O1—C6—N1	123.6 (3)
S1—C2—H2	122.3	O1—C6—C5	122.0 (3)
C2—C3—C4	107.7 (7)	N1—C6—C5	114.5 (3)
C2—C3—H3	126.2	C12—C7—C8	119.5 (3)
C4—C3—H3	126.2	C12—C7—N1	118.5 (3)
C1—C4—C3	114.9 (11)	C8—C7—N1	122.1 (3)
C1—C4—H4	122.6	C9—C8—C7	120.1 (3)
C3—C4—H4	122.6	C9—C8—H8	119.9
C1'—S1'—C3'	94.5 (5)	C7—C8—H8	119.9
C4'—C1'—C5	126.1 (14)	C10—C9—C8	119.7 (3)
C4'—C1'—S1'	114.4 (14)	C10—C9—H9	120.2
C5—C1'—S1'	119.4 (4)	C8—C9—H9	120.2
C3'—C2'—C4'	105.2 (11)	C11—C10—C9	121.3 (3)
C3'—C2'—H2'	127.4	C11—C10—Br	119.6 (2)
C4'—C2'—H2'	127.4	C9—C10—Br	119.1 (2)
C2'—C3'—S1'	117.9 (4)	C10—C11—C12	118.9 (3)
C2'—C3'—H3'	121.1	C10—C11—H11	120.5
S1'—C3'—H3'	121.1	C12—C11—H11	120.5
C1'—C4'—C2'	108.0 (19)	C7—C12—C11	120.4 (3)
C1'—C4'—H4'	126.0	C7—C12—H12	119.8
C2'—C4'—H4'	126.0	C11—C12—H12	119.8
C1'—C5—C6	113.6 (3)
C2—S1—C1—C4	−2.5 (10)	C7—N1—C6—O1	−1.5 (5)
C2—S1—C1—C5	−179.0 (3)	C7—N1—C6—C5	178.7 (3)
C1—S1—C2—C3	0.8 (4)	C1'—C5—C6—O1	9.4 (5)
S1—C2—C3—C4	1.0 (9)	C1—C5—C6—O1	9.4 (5)
C5—C1—C4—C3	179.8 (7)	C1'—C5—C6—N1	−170.8 (3)
S1—C1—C4—C3	3.6 (17)	C1—C5—C6—N1	−170.8 (3)
C2—C3—C4—C1	−3.0 (16)	C6—N1—C7—C12	−144.4 (3)
C3'—S1'—C1'—C4'	−0.6 (19)	C6—N1—C7—C8	35.0 (5)
C3'—S1'—C1'—C5	178.7 (3)	C12—C7—C8—C9	0.5 (5)
C4'—C2'—C3'—S1'	0.1 (13)	N1—C7—C8—C9	−178.9 (3)
C1'—S1'—C3'—C2'	0.3 (6)	C7—C8—C9—C10	0.6 (5)
C5—C1'—C4'—C2'	−178.6 (8)	C8—C9—C10—C11	−2.2 (5)
S1'—C1'—C4'—C2'	1(3)	C8—C9—C10—Br	176.1 (2)
C3'—C2'—C4'—C1'	0(2)	C9—C10—C11—C12	2.6 (5)
C4'—C1'—C5—C6	89.3 (18)	Br—C10—C11—C12	−175.7 (2)
S1'—C1'—C5—C6	−89.9 (5)	C8—C7—C12—C11	0.0 (5)
C4—C1—C5—C6	−87.3 (12)	N1—C7—C12—C11	179.4 (3)
S1—C1—C5—C6	88.4 (4)	C10—C11—C12—C7	−1.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1i	0.875 (17)	2.00 (2)	2.848 (3)	162 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1i	0.88 (2)	2.00 (2)	2.848 (3)	162 (3)

Symmetry code: (i) .