2-(Benzo[d]thia-zol-2-ylsulfon-yl)-1-(4-bromo-phen-yl)ethanone.

In the title mol-ecule, C(15)H(10)BrNO(3)S(2), the dihedral angle between the benzothia-zole ring system and the benzene ring is 67.57 (12)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O inter-actions. In addition, there is an inter-molecular Br⋯C [3.379 (3) Å] contact which is shorter than the sum of the van der Waals radii of these atoms.

Related literature

For bond-length data, see Allen et al. (1987 ▶). For the applications of related compounds in organic synthesis, see: Marco et al. (1995 ▶); Fuju et al. (1988 ▶); Ni et al. (2006 ▶); Grossert et al. (1984 ▶); Oishi et al. (1988) ▶; Antane et al. (2004 ▶). For the biological activity of related compounds see, Padmavathi et al. (2008 ▶). For related structures see: Loghmani-Khouzani et al. (2008 ▶, 2009a ▶,b ▶); Munoz et al. (2005 ▶); Suryakiran et al. (2007 ▶).

Experimental

Crystal data

C15H10BrNO3S2

M = 396.27

Monoclinic,

a = 5.6695 (10) Å

b = 24.489 (4) Å

c = 10.7042 (19) Å

β = 94.178 (3)°

V = 1482.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.07 mm−1

T = 296 K

0.42 × 0.30 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.363, T max = 0.864

6602 measured reflections

2564 independent reflections

2140 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.089

S = 1.03

2564 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809053112/lh2971sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053112/lh2971Isup2.hkl

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

C15H10BrNO3S2	F(000) = 792
Mr = 396.27	Dx = 1.776 Mg m−3
Monoclinic, P21/n	Melting point: 470 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.6695 (10) Å	Cell parameters from 3475 reflections
b = 24.489 (4) Å	θ = 2.5–30.3°
c = 10.7042 (19) Å	µ = 3.07 mm−1
β = 94.178 (3)°	T = 296 K
V = 1482.2 (5) Å3	Plate, colourless
Z = 4	0.42 × 0.30 × 0.05 mm

Bruker SMART APEXII CCD area-detector diffractometer	2564 independent reflections
Radiation source: fine-focus sealed tube	2140 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.363, Tmax = 0.864	k = −29→23
6602 measured reflections	l = −12→12

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) = 0.089	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3
2564 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.83 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
Br1	0.73768 (6)	0.334681 (12)	0.50902 (3)	0.02981 (14)
C6	0.1307 (5)	0.72648 (11)	0.1923 (3)	0.0176 (6)
C5	0.2796 (6)	0.77145 (12)	0.2066 (3)	0.0254 (7)
H5A	0.4151	0.7739	0.1630	0.031*
C4	0.2209 (6)	0.81234 (12)	0.2872 (3)	0.0285 (8)
H4A	0.3187	0.8427	0.2984	0.034*
C3	0.0172 (6)	0.80883 (13)	0.3521 (3)	0.0278 (8)
H3A	−0.0167	0.8368	0.4069	0.033*
C2	−0.1355 (6)	0.76516 (12)	0.3374 (3)	0.0234 (7)
H2A	−0.2719	0.7633	0.3805	0.028*
C1	−0.0776 (5)	0.72389 (11)	0.2555 (3)	0.0180 (6)
C7	0.0046 (5)	0.64645 (11)	0.1287 (3)	0.0152 (6)
C8	0.2422 (5)	0.54542 (11)	0.1342 (3)	0.0161 (6)
H8A	0.2775	0.5135	0.0852	0.019*
H8B	0.3830	0.5680	0.1414	0.019*
C9	0.1874 (5)	0.52687 (11)	0.2645 (3)	0.0187 (7)
C10	0.3307 (5)	0.48088 (11)	0.3204 (3)	0.0165 (6)
C15	0.5345 (5)	0.46196 (11)	0.2724 (3)	0.0194 (7)
H15A	0.5888	0.4782	0.2013	0.023*
C14	0.6590 (5)	0.41889 (11)	0.3296 (3)	0.0208 (7)
H14A	0.7975	0.4063	0.2979	0.025*
C13	0.5753 (5)	0.39509 (11)	0.4333 (3)	0.0202 (7)
C12	0.3738 (6)	0.41345 (11)	0.4839 (3)	0.0225 (7)
H12A	0.3209	0.3971	0.5551	0.027*
C11	0.2519 (6)	0.45649 (12)	0.4270 (3)	0.0226 (7)
H11A	0.1154	0.4694	0.4603	0.027*
N1	0.1732 (4)	0.68070 (9)	0.1198 (2)	0.0176 (6)
O2	0.0855 (4)	0.59122 (8)	−0.07094 (18)	0.0240 (5)
O1	−0.2124 (4)	0.55675 (8)	0.0658 (2)	0.0225 (5)
O3	0.0318 (4)	0.54839 (9)	0.3174 (2)	0.0296 (6)
S2	0.01146 (13)	0.58258 (3)	0.05223 (7)	0.01619 (19)
S1	−0.22406 (13)	0.66352 (3)	0.21941 (7)	0.0196 (2)

	U11	U22	U33	U12	U13	U23
Br1	0.0356 (2)	0.0266 (2)	0.0268 (2)	0.01244 (13)	−0.00100 (16)	0.00696 (13)
C6	0.0204 (16)	0.0135 (14)	0.0185 (15)	0.0026 (12)	−0.0011 (13)	0.0023 (11)
C5	0.0218 (17)	0.0234 (16)	0.0309 (18)	−0.0031 (13)	0.0000 (14)	0.0022 (14)
C4	0.034 (2)	0.0193 (16)	0.0311 (19)	−0.0034 (14)	−0.0076 (16)	−0.0036 (14)
C3	0.035 (2)	0.0209 (16)	0.0269 (18)	0.0068 (14)	−0.0024 (16)	−0.0078 (13)
C2	0.0246 (17)	0.0228 (16)	0.0227 (17)	0.0080 (13)	0.0014 (14)	−0.0007 (12)
C1	0.0195 (16)	0.0144 (13)	0.0199 (16)	0.0022 (12)	−0.0008 (13)	0.0027 (12)
C7	0.0165 (15)	0.0131 (14)	0.0159 (16)	0.0031 (11)	0.0013 (13)	0.0010 (11)
C8	0.0169 (15)	0.0120 (13)	0.0196 (16)	0.0020 (11)	0.0029 (13)	0.0013 (11)
C9	0.0219 (16)	0.0167 (14)	0.0180 (16)	−0.0032 (13)	0.0045 (14)	−0.0015 (12)
C10	0.0199 (16)	0.0140 (13)	0.0161 (15)	−0.0011 (12)	0.0052 (13)	−0.0004 (11)
C15	0.0198 (16)	0.0226 (15)	0.0168 (16)	−0.0014 (12)	0.0085 (13)	0.0031 (12)
C14	0.0176 (15)	0.0248 (16)	0.0210 (16)	0.0048 (12)	0.0078 (13)	−0.0007 (13)
C13	0.0275 (17)	0.0164 (14)	0.0161 (16)	0.0040 (13)	−0.0015 (14)	0.0013 (12)
C12	0.0281 (18)	0.0223 (15)	0.0181 (16)	0.0040 (14)	0.0100 (14)	0.0070 (12)
C11	0.0234 (17)	0.0271 (16)	0.0184 (16)	0.0059 (13)	0.0080 (14)	0.0003 (13)
N1	0.0183 (14)	0.0164 (12)	0.0184 (13)	0.0011 (10)	0.0044 (11)	0.0023 (10)
O2	0.0311 (12)	0.0264 (11)	0.0148 (11)	0.0048 (9)	0.0039 (10)	0.0014 (8)
O1	0.0169 (11)	0.0198 (10)	0.0310 (13)	−0.0034 (9)	0.0028 (10)	−0.0038 (9)
O3	0.0376 (14)	0.0288 (12)	0.0244 (12)	0.0144 (10)	0.0170 (11)	0.0054 (10)
S2	0.0176 (4)	0.0148 (4)	0.0163 (4)	0.0011 (3)	0.0025 (3)	−0.0004 (3)
S1	0.0183 (4)	0.0182 (4)	0.0230 (4)	−0.0002 (3)	0.0072 (3)	0.0000 (3)

Br1—C13	1.893 (3)	C8—S2	1.773 (3)
C6—C5	1.389 (4)	C8—H8A	0.9700
C6—N1	1.395 (4)	C8—H8B	0.9700
C6—C1	1.404 (4)	C9—O3	1.204 (4)
C5—C4	1.378 (5)	C9—C10	1.489 (4)
C5—H5A	0.9300	C10—C15	1.378 (4)
C4—C3	1.393 (5)	C10—C11	1.391 (4)
C4—H4A	0.9300	C15—C14	1.386 (4)
C3—C2	1.378 (4)	C15—H15A	0.9300
C3—H3A	0.9300	C14—C13	1.369 (4)
C2—C1	1.393 (4)	C14—H14A	0.9300
C2—H2A	0.9300	C13—C12	1.375 (4)
C1—S1	1.726 (3)	C12—C11	1.378 (4)
C7—N1	1.281 (4)	C12—H12A	0.9300
C7—S1	1.726 (3)	C11—H11A	0.9300
C7—S2	1.767 (3)	O2—S2	1.428 (2)
C8—C9	1.520 (4)	O1—S2	1.435 (2)
C5—C6—N1	124.8 (3)	O3—C9—C8	120.5 (3)
C5—C6—C1	120.5 (3)	C10—C9—C8	116.9 (3)
N1—C6—C1	114.6 (2)	C15—C10—C11	119.3 (3)
C4—C5—C6	118.2 (3)	C15—C10—C9	123.5 (3)
C4—C5—H5A	120.9	C11—C10—C9	117.1 (3)
C6—C5—H5A	120.9	C10—C15—C14	120.3 (3)
C5—C4—C3	120.9 (3)	C10—C15—H15A	119.8
C5—C4—H4A	119.5	C14—C15—H15A	119.8
C3—C4—H4A	119.5	C13—C14—C15	119.1 (3)
C2—C3—C4	121.8 (3)	C13—C14—H14A	120.5
C2—C3—H3A	119.1	C15—C14—H14A	120.5
C4—C3—H3A	119.1	C14—C13—C12	121.8 (3)
C3—C2—C1	117.4 (3)	C14—C13—Br1	119.6 (2)
C3—C2—H2A	121.3	C12—C13—Br1	118.6 (2)
C1—C2—H2A	121.3	C13—C12—C11	118.7 (3)
C2—C1—C6	121.0 (3)	C13—C12—H12A	120.6
C2—C1—S1	129.1 (2)	C11—C12—H12A	120.6
C6—C1—S1	109.8 (2)	C12—C11—C10	120.7 (3)
N1—C7—S1	118.6 (2)	C12—C11—H11A	119.7
N1—C7—S2	120.2 (2)	C10—C11—H11A	119.7
S1—C7—S2	121.18 (17)	C7—N1—C6	109.0 (3)
C9—C8—S2	114.5 (2)	O2—S2—O1	118.72 (13)
C9—C8—H8A	108.6	O2—S2—C7	108.34 (13)
S2—C8—H8A	108.6	O1—S2—C7	107.07 (13)
C9—C8—H8B	108.6	O2—S2—C8	106.09 (13)
S2—C8—H8B	108.6	O1—S2—C8	110.47 (13)
H8A—C8—H8B	107.6	C7—S2—C8	105.39 (13)
O3—C9—C10	122.6 (3)	C1—S1—C7	87.97 (14)
N1—C6—C5—C4	−176.3 (3)	C14—C13—C12—C11	1.0 (5)
C1—C6—C5—C4	2.1 (4)	Br1—C13—C12—C11	−178.3 (2)
C6—C5—C4—C3	−0.4 (4)	C13—C12—C11—C10	0.1 (5)
C5—C4—C3—C2	−1.0 (5)	C15—C10—C11—C12	−0.7 (4)
C4—C3—C2—C1	0.6 (4)	C9—C10—C11—C12	179.6 (3)
C3—C2—C1—C6	1.1 (4)	S1—C7—N1—C6	1.1 (3)
C3—C2—C1—S1	178.0 (2)	S2—C7—N1—C6	−177.54 (19)
C5—C6—C1—C2	−2.5 (4)	C5—C6—N1—C7	178.7 (3)
N1—C6—C1—C2	176.0 (3)	C1—C6—N1—C7	0.3 (3)
C5—C6—C1—S1	−180.0 (2)	N1—C7—S2—O2	−43.5 (3)
N1—C6—C1—S1	−1.4 (3)	S1—C7—S2—O2	137.99 (16)
S2—C8—C9—O3	−19.1 (4)	N1—C7—S2—O1	−172.6 (2)
S2—C8—C9—C10	159.8 (2)	S1—C7—S2—O1	8.8 (2)
O3—C9—C10—C15	−168.3 (3)	N1—C7—S2—C8	69.7 (3)
C8—C9—C10—C15	12.9 (4)	S1—C7—S2—C8	−108.81 (18)
O3—C9—C10—C11	11.5 (4)	C9—C8—S2—O2	−174.09 (19)
C8—C9—C10—C11	−167.4 (3)	C9—C8—S2—O1	−44.2 (2)
C11—C10—C15—C14	0.3 (4)	C9—C8—S2—C7	71.1 (2)
C9—C10—C15—C14	180.0 (3)	C2—C1—S1—C7	−175.6 (3)
C10—C15—C14—C13	0.7 (4)	C6—C1—S1—C7	1.6 (2)
C15—C14—C13—C12	−1.4 (5)	N1—C7—S1—C1	−1.6 (2)
C15—C14—C13—Br1	177.9 (2)	S2—C7—S1—C1	176.96 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2i	0.93	2.56	3.420 (4)	154
C8—H8A···O1ii	0.97	2.37	3.289 (3)	158
C8—H8B···O1iii	0.97	2.50	3.241 (4)	133
C14—H14A···O2iv	0.93	2.56	3.226 (4)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2i	0.93	2.56	3.420 (4)	154
C8—H8A⋯O1ii	0.97	2.37	3.289 (3)	158
C8—H8B⋯O1iii	0.97	2.50	3.241 (4)	133
C14—H14A⋯O2iv	0.93	2.56	3.226 (4)	128

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .