(2E)-3-(2-Bromo­phen­yl)-1-(5-bromo­thio­phen-2-yl)prop-2-en-1-one

Vepuri, S.B.; Devarajegowda, H.C.; Jeyaseelan, S.; Anbazhagan, S.; Prasad, Y.R.

doi:10.1107/S1600536812047939

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3456

doi:10.1107/S1600536812047939

Open

access

(2E)-3-(2-Bromophenyl)-1-(5-bromothiophen-2-yl)prop-2-en-1-one

Suresh B. Vepuri,^a H. C. Devarajegowda,^b ^* S. Jeyaseelan,^b S. Anbazhagan ^c and Y. Rajendra Prasad ^d

^aInstitute of Pharmacy, GITAM University, Visakhapatnam-45, Andhrapradesh, India, ^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^cKaruna College of Pharmacy, Thirumittacode, Palakad 679 533, Kerala, India, and ^dCollege of Pharmacy, Andhra University, Visakhapatnam, Andhrapradesh, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 9 November 2012; accepted 21 November 2012; online 28 November 2012)

The asymmetric unit of the title compound, C₁₃H₈Br₂OS, contains two molecules, in which the dihedral angles between the thiophene and benzene rings are 10.5 (3) and 33.2 (4)°. There are no significant directional interactions in the crystal.

Related literature

For further details of conformational modelling, see: Pascard (1995 ); Thomas et al. (2004 ). For related structures, see: Liang et al. (2011 ); Alex et al. (1993 ); Li & Su (1993 ).

Experimental

Crystal data

C₁₃H₈Br₂OS
M_r = 372.07
Monoclinic, C c
a = 34.524 (8) Å
b = 3.9994 (9) Å
c = 23.428 (5) Å
β = 126.804 (3)°
V = 2590.1 (10) Å³
Z = 8
Mo Kα radiation
μ = 6.40 mm⁻¹
T = 293 K
0.22 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.228, T_max = 1.000
13574 measured reflections
5988 independent reflections
4266 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.109
S = 0.97
5988 reflections
308 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.44 e Å⁻³
Absolute structure: Flack (1983 ), 2846 Friedel pairs
Flack parameter: 0.000 (13)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812047939/hb6986sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047939/hb6986Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812047939/hb6986Isup3.cml

checkCIF report

Comment top

Apart from numerous applications in basic research, crystal structure conformation of small molecules has always been the choice for binding energy calculations in molecular modeling during drug discovery process (Pascard, 1995). The reason is it provides coordinates for the most favorable stereo positions of the atoms in solid state.Use of the low energy conformation obtained in this bound state may provide good rationality in drug design study. As a part of our effort in designing lead compound for human aldose reductase inhibiton we are interested in studying the crystal structure conformation of (2E)-1-(5-bromothiophen-2-yl)-3-[4-(dimethylamino) phenyl]prop-2-en-1-one. In our docking studies the title chalcone has shown good binding affinity with dock score -9.490027 calculated by using GLIDE scoring (Thomas et al., 2004) function from Schrodinger 9.2v molecular modeling suite.

The asymmetric unit of (2E)-1-(5-bromothiophen-2-yl)-3- (2-bromophenyl)prop-2-en-1-one, C₁₃H₈Br₂OS, contain two molecules (Fig. 1). The five-membered thiophene rings (S3a\C5a\···C8a) & (S3b\C5b\···C8b) are not coplanar with the phenyl rings (C12a\C13a\···C17a) & (C12b\C13b\···C17b) system; the dihedral angle between the two planes are 10.5 (3)° and 33.2 (4)° of A and B molecules respectivelly. Bond distances and bond angles are in good agreement with those observed in related crystal structures (Liang et al., 2011; Alex et al., 1993; Li et al., 1993). The packing of molecules in the crystal structure is depicted in Fig. 2.

Related literature top

For further details of conformational modelling, see: Pascard (1995); Thomas et al. (2004). For related structures, see: Liang et al. (2011); Alex et al. (1993); Li et al. (1993).

Experimental top

A mixture of 2-acetyl-5-bromothiophene (0.01 mole) and 2-bromobenzaldehyde (0.01 mole) were stirred in ethanol (30 ml) and then an aqueous solution of potassium hydroxide (40%, 15 ml)was added to it. The mixture was kept over night at room temperature and then it was poured into crushed ice and acidified with dilute hydrochloric acid. The precipiteted chalcone was filtered and crystallized from ethanol as colourless prisms.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of the molecules.

(2E)-3-(2-Bromophenyl)-1-(5-bromothiophen-2-yl)prop-2-en-1-one top

Crystal data top

C₁₃H₈Br₂OS	F(000) = 1440
M_r = 372.07	D_x = 1.908 Mg m⁻³
Monoclinic, Cc	Melting point: 403 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 34.524 (8) Å	Cell parameters from 5988 reflections
b = 3.9994 (9) Å	θ = 1.8–28.0°
c = 23.428 (5) Å	µ = 6.40 mm⁻¹
β = 126.804 (3)°	T = 293 K
V = 2590.1 (10) Å³	Prism, colourless
Z = 8	0.22 × 0.15 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	5988 independent reflections
Radiation source: Mova (Mo) X-ray Source	4266 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.051
Detector resolution: 16.0839 pixels mm^-1	θ_max = 28.0°, θ_min = 1.8°
ω scans	h = −44→44
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −5→5
T_min = 0.228, T_max = 1.000	l = −30→30
13574 measured reflections

Refinement top

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0425P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
5988 reflections	Δρ_max = 0.58 e Å⁻³
308 parameters	Δρ_min = −0.44 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2846 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (13)

Crystal data top

C₁₃H₈Br₂OS	V = 2590.1 (10) Å³
M_r = 372.07	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 34.524 (8) Å	µ = 6.40 mm⁻¹
b = 3.9994 (9) Å	T = 293 K
c = 23.428 (5) Å	0.22 × 0.15 × 0.12 mm
β = 126.804 (3)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	5988 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	4266 reflections with I > 2σ(I)
T_min = 0.228, T_max = 1.000	R_int = 0.051
13574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.109	Δρ_max = 0.58 e Å⁻³
S = 0.97	Δρ_min = −0.44 e Å⁻³
5988 reflections	Absolute structure: Flack (1983), 2846 Friedel pairs
308 parameters	Absolute structure parameter: 0.000 (13)
2 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1A	0.49316 (2)	0.58296 (18)	0.54216 (3)	0.05287 (19)
Br2A	0.83387 (2)	−0.64813 (18)	0.74346 (3)	0.0554 (2)
S3A	0.58670 (6)	0.2854 (4)	0.57198 (9)	0.0491 (4)
O4A	0.6766 (2)	−0.0276 (16)	0.6126 (3)	0.0756 (17)
C5A	0.5553 (2)	0.3956 (14)	0.6035 (4)	0.0416 (14)
C6A	0.5789 (2)	0.3287 (16)	0.6733 (3)	0.0468 (16)
H6A	0.5664	0.3709	0.6983	0.056*
C7A	0.6247 (3)	0.1873 (16)	0.7037 (4)	0.0498 (17)
H7A	0.6463	0.1295	0.7516	0.060*
C8A	0.6338 (2)	0.1449 (14)	0.6553 (3)	0.0391 (14)
C9A	0.6763 (3)	0.0017 (17)	0.6631 (4)	0.0466 (15)
C10A	0.7161 (3)	−0.1089 (17)	0.7347 (4)	0.0531 (18)
H10A	0.7143	−0.0709	0.7722	0.064*
C11A	0.7544 (2)	−0.2607 (15)	0.7476 (4)	0.0445 (15)
H11A	0.7537	−0.3056	0.7081	0.053*
C12A	0.7978 (2)	−0.3670 (14)	0.8162 (4)	0.0404 (14)
C13A	0.8033 (3)	−0.3032 (18)	0.8802 (4)	0.0549 (18)
H13A	0.7785	−0.1964	0.8779	0.066*
C14A	0.8448 (3)	−0.3956 (19)	0.9463 (4)	0.0544 (18)
H14A	0.8472	−0.3529	0.9873	0.065*
C15A	0.8820 (3)	−0.5488 (17)	0.9512 (4)	0.0535 (17)
H15A	0.9097	−0.6088	0.9957	0.064*
C16A	0.8787 (3)	−0.6158 (15)	0.8903 (4)	0.0495 (16)
H16A	0.9043	−0.7155	0.8934	0.059*
C17A	0.8364 (2)	−0.5300 (14)	0.8248 (3)	0.0405 (14)
Br1B	0.84144 (3)	−1.0016 (2)	1.09708 (4)	0.0628 (2)
Br2B	0.47871 (3)	−0.1788 (2)	0.68156 (4)	0.0673 (2)
S3B	0.75065 (6)	−0.6749 (4)	0.96145 (9)	0.0487 (4)
O4B	0.6618 (2)	−0.3491 (14)	0.8424 (3)	0.0657 (14)
C5B	0.7785 (2)	−0.8334 (15)	1.0463 (3)	0.0461 (16)
C6B	0.7510 (3)	−0.8115 (17)	1.0687 (4)	0.0541 (17)
H6B	0.7601	−0.8887	1.1126	0.065*
C7B	0.7066 (2)	−0.6571 (17)	1.0175 (3)	0.0492 (16)
H7B	0.6832	−0.6189	1.0248	0.059*
C8B	0.7003 (2)	−0.5683 (15)	0.9569 (3)	0.0418 (15)
C9B	0.6608 (3)	−0.4037 (18)	0.8926 (4)	0.0468 (14)
C10B	0.6193 (2)	−0.2910 (17)	0.8921 (3)	0.0478 (16)
H10B	0.6217	−0.3147	0.9336	0.057*
C11B	0.5802 (3)	−0.1621 (17)	0.8367 (4)	0.0484 (16)
H11B	0.5789	−0.1439	0.7959	0.058*
C12B	0.5375 (2)	−0.0406 (16)	0.8307 (3)	0.0421 (15)
C13B	0.5440 (3)	0.0730 (18)	0.8926 (4)	0.0573 (18)
H13B	0.5748	0.0715	0.9357	0.069*
C14B	0.5053 (3)	0.187 (2)	0.8903 (4)	0.066 (2)
H14B	0.5102	0.2568	0.9320	0.080*
C15B	0.4599 (3)	0.198 (2)	0.8271 (5)	0.064 (2)
H15B	0.4339	0.2748	0.8258	0.077*
C16B	0.4530 (3)	0.0956 (18)	0.7660 (4)	0.0573 (19)
H16B	0.4223	0.1065	0.7227	0.069*
C17B	0.4913 (3)	−0.0237 (16)	0.7683 (4)	0.0484 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.0393 (4)	0.0547 (3)	0.0606 (5)	0.0062 (3)	0.0277 (4)	0.0033 (4)
Br2A	0.0560 (5)	0.0566 (4)	0.0650 (5)	0.0045 (3)	0.0424 (4)	−0.0061 (4)
S3A	0.0474 (10)	0.0591 (10)	0.0469 (9)	0.0091 (8)	0.0315 (9)	0.0035 (8)
O4A	0.060 (4)	0.114 (5)	0.066 (4)	0.028 (3)	0.045 (3)	0.009 (3)
C5A	0.035 (3)	0.034 (3)	0.055 (4)	−0.004 (3)	0.026 (3)	−0.005 (3)
C6A	0.047 (4)	0.057 (4)	0.043 (4)	0.009 (3)	0.031 (3)	0.004 (3)
C7A	0.049 (4)	0.052 (4)	0.048 (4)	0.010 (3)	0.029 (4)	0.004 (3)
C8A	0.042 (4)	0.034 (3)	0.048 (4)	0.003 (3)	0.030 (3)	0.002 (3)
C9A	0.046 (4)	0.052 (4)	0.051 (4)	0.002 (3)	0.034 (4)	0.000 (3)
C10A	0.054 (5)	0.053 (4)	0.069 (5)	0.006 (3)	0.045 (4)	0.003 (4)
C11A	0.037 (4)	0.049 (3)	0.054 (4)	0.001 (3)	0.030 (3)	0.004 (3)
C12A	0.035 (3)	0.037 (3)	0.051 (4)	0.000 (3)	0.027 (3)	0.004 (3)
C13A	0.054 (5)	0.058 (4)	0.074 (5)	0.004 (4)	0.050 (4)	0.000 (4)
C14A	0.053 (5)	0.062 (4)	0.045 (4)	−0.007 (4)	0.028 (4)	−0.003 (3)
C15A	0.046 (4)	0.055 (4)	0.056 (4)	−0.001 (3)	0.029 (4)	0.000 (3)
C16A	0.040 (4)	0.044 (4)	0.061 (4)	0.000 (3)	0.028 (4)	−0.001 (3)
C17A	0.048 (4)	0.031 (3)	0.050 (4)	−0.002 (3)	0.033 (4)	0.000 (3)
Br1B	0.0518 (5)	0.0594 (4)	0.0590 (5)	0.0080 (4)	0.0235 (4)	−0.0050 (4)
Br2B	0.0649 (6)	0.0759 (5)	0.0509 (4)	0.0063 (4)	0.0293 (4)	−0.0050 (4)
S3B	0.0485 (10)	0.0561 (10)	0.0487 (9)	−0.0001 (8)	0.0330 (9)	0.0004 (8)
O4B	0.064 (4)	0.090 (4)	0.050 (3)	0.016 (3)	0.037 (3)	0.014 (3)
C5B	0.049 (4)	0.034 (3)	0.048 (4)	−0.005 (3)	0.025 (4)	−0.004 (3)
C6B	0.057 (5)	0.058 (4)	0.049 (4)	0.004 (4)	0.033 (4)	0.008 (3)
C7B	0.042 (4)	0.064 (4)	0.048 (4)	−0.003 (3)	0.030 (4)	−0.002 (3)
C8B	0.050 (4)	0.039 (3)	0.043 (4)	−0.003 (3)	0.032 (3)	−0.003 (3)
C9B	0.045 (4)	0.049 (3)	0.042 (3)	−0.001 (3)	0.024 (3)	0.000 (3)
C10B	0.040 (4)	0.060 (4)	0.037 (3)	0.000 (3)	0.019 (3)	0.005 (3)
C11B	0.050 (4)	0.056 (4)	0.045 (4)	−0.002 (3)	0.032 (4)	0.000 (3)
C12B	0.035 (4)	0.044 (4)	0.040 (3)	−0.001 (3)	0.019 (3)	0.006 (3)
C13B	0.058 (5)	0.061 (4)	0.062 (5)	−0.010 (4)	0.041 (4)	−0.003 (4)
C14B	0.072 (6)	0.077 (6)	0.056 (5)	0.008 (5)	0.042 (5)	−0.009 (4)
C15B	0.059 (5)	0.068 (5)	0.076 (6)	0.003 (4)	0.046 (5)	−0.004 (4)
C16B	0.046 (5)	0.061 (5)	0.056 (4)	0.008 (3)	0.026 (4)	0.011 (4)
C17B	0.059 (5)	0.043 (4)	0.055 (4)	0.005 (3)	0.040 (4)	0.007 (3)

Geometric parameters (Å, º) top

Br1A—C5A	1.880 (6)	Br1B—C5B	1.870 (7)
Br2A—C17A	1.913 (6)	Br2B—C17B	1.909 (7)
S3A—C5A	1.694 (6)	S3B—C5B	1.729 (7)
S3A—C8A	1.723 (7)	S3B—C8B	1.731 (7)
O4A—C9A	1.197 (8)	O4B—C9B	1.217 (9)
C5A—C6A	1.346 (9)	C5B—C6B	1.333 (10)
C6A—C7A	1.407 (9)	C6B—C7B	1.403 (10)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.354 (9)	C7B—C8B	1.350 (9)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.481 (9)	C8B—C9B	1.449 (10)
C9A—C10A	1.461 (10)	C9B—C10B	1.496 (11)
C10A—C11A	1.316 (9)	C10B—C11B	1.293 (9)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.458 (9)	C11B—C12B	1.478 (10)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C17A	1.385 (9)	C12B—C17B	1.376 (9)
C12A—C13A	1.416 (10)	C12B—C13B	1.402 (10)
C13A—C14A	1.388 (11)	C13B—C14B	1.382 (11)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.364 (10)	C14B—C15B	1.368 (11)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.388 (10)	C15B—C16B	1.367 (10)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.387 (9)	C16B—C17B	1.376 (10)
C16A—H16A	0.9300	C16B—H16B	0.9300

C5A—S3A—C8A	90.4 (3)	C5B—S3B—C8B	90.4 (3)
C6A—C5A—S3A	113.4 (5)	C6B—C5B—S3B	113.1 (5)
C6A—C5A—Br1A	126.2 (5)	C6B—C5B—Br1B	127.1 (5)
S3A—C5A—Br1A	120.4 (4)	S3B—C5B—Br1B	119.8 (4)
C5A—C6A—C7A	112.0 (6)	C5B—C6B—C7B	111.4 (6)
C5A—C6A—H6A	124.0	C5B—C6B—H6B	124.3
C7A—C6A—H6A	124.0	C7B—C6B—H6B	124.3
C8A—C7A—C6A	112.2 (6)	C8B—C7B—C6B	114.8 (6)
C8A—C7A—H7A	123.9	C8B—C7B—H7B	122.6
C6A—C7A—H7A	123.9	C6B—C7B—H7B	122.6
C7A—C8A—C9A	130.8 (6)	C7B—C8B—C9B	132.2 (7)
C7A—C8A—S3A	112.0 (5)	C7B—C8B—S3B	110.4 (5)
C9A—C8A—S3A	117.3 (5)	C9B—C8B—S3B	117.4 (5)
O4A—C9A—C10A	123.1 (7)	O4B—C9B—C8B	122.2 (7)
O4A—C9A—C8A	120.8 (7)	O4B—C9B—C10B	121.4 (7)
C10A—C9A—C8A	116.1 (6)	C8B—C9B—C10B	116.4 (6)
C11A—C10A—C9A	121.9 (7)	C11B—C10B—C9B	123.1 (6)
C11A—C10A—H10A	119.0	C11B—C10B—H10B	118.5
C9A—C10A—H10A	119.0	C9B—C10B—H10B	118.5
C10A—C11A—C12A	128.0 (7)	C10B—C11B—C12B	127.4 (6)
C10A—C11A—H11A	116.0	C10B—C11B—H11B	116.3
C12A—C11A—H11A	116.0	C12B—C11B—H11B	116.3
C17A—C12A—C13A	115.1 (6)	C17B—C12B—C13B	116.6 (6)
C17A—C12A—C11A	124.1 (6)	C17B—C12B—C11B	124.9 (6)
C13A—C12A—C11A	120.8 (6)	C13B—C12B—C11B	118.4 (6)
C14A—C13A—C12A	121.8 (7)	C14B—C13B—C12B	120.9 (7)
C14A—C13A—H13A	119.1	C14B—C13B—H13B	119.5
C12A—C13A—H13A	119.1	C12B—C13B—H13B	119.5
C15A—C14A—C13A	120.3 (7)	C15B—C14B—C13B	120.6 (7)
C15A—C14A—H14A	119.9	C15B—C14B—H14B	119.7
C13A—C14A—H14A	119.9	C13B—C14B—H14B	119.7
C14A—C15A—C16A	120.5 (7)	C16B—C15B—C14B	119.4 (7)
C14A—C15A—H15A	119.8	C16B—C15B—H15B	120.3
C16A—C15A—H15A	119.8	C14B—C15B—H15B	120.3
C17A—C16A—C15A	118.2 (7)	C15B—C16B—C17B	120.2 (7)
C17A—C16A—H16A	120.9	C15B—C16B—H16B	119.9
C15A—C16A—H16A	120.9	C17B—C16B—H16B	119.9
C12A—C17A—C16A	124.1 (6)	C12B—C17B—C16B	122.3 (6)
C12A—C17A—Br2A	120.4 (5)	C12B—C17B—Br2B	119.7 (5)
C16A—C17A—Br2A	115.5 (5)	C16B—C17B—Br2B	118.0 (6)

C8A—S3A—C5A—C6A	−0.3 (5)	C8B—S3B—C5B—C6B	1.0 (5)
C8A—S3A—C5A—Br1A	−179.1 (4)	C8B—S3B—C5B—Br1B	−177.5 (4)
S3A—C5A—C6A—C7A	1.0 (8)	S3B—C5B—C6B—C7B	−1.3 (8)
Br1A—C5A—C6A—C7A	179.7 (5)	Br1B—C5B—C6B—C7B	177.1 (5)
C5A—C6A—C7A—C8A	−1.4 (9)	C5B—C6B—C7B—C8B	1.0 (9)
C6A—C7A—C8A—C9A	−178.8 (6)	C6B—C7B—C8B—C9B	−179.3 (7)
C6A—C7A—C8A—S3A	1.2 (8)	C6B—C7B—C8B—S3B	−0.2 (8)
C5A—S3A—C8A—C7A	−0.5 (5)	C5B—S3B—C8B—C7B	−0.4 (5)
C5A—S3A—C8A—C9A	179.4 (5)	C5B—S3B—C8B—C9B	178.8 (5)
C7A—C8A—C9A—O4A	176.7 (8)	C7B—C8B—C9B—O4B	−178.9 (8)
S3A—C8A—C9A—O4A	−3.2 (9)	S3B—C8B—C9B—O4B	2.1 (10)
C7A—C8A—C9A—C10A	−1.3 (11)	C7B—C8B—C9B—C10B	3.5 (11)
S3A—C8A—C9A—C10A	178.7 (5)	S3B—C8B—C9B—C10B	−175.5 (5)
O4A—C9A—C10A—C11A	−2.6 (11)	O4B—C9B—C10B—C11B	7.4 (12)
C8A—C9A—C10A—C11A	175.4 (6)	C8B—C9B—C10B—C11B	−175.0 (7)
C9A—C10A—C11A—C12A	176.2 (6)	C9B—C10B—C11B—C12B	−179.4 (7)
C10A—C11A—C12A—C17A	179.1 (7)	C10B—C11B—C12B—C17B	−154.3 (7)
C10A—C11A—C12A—C13A	−1.7 (10)	C10B—C11B—C12B—C13B	27.0 (11)
C17A—C12A—C13A—C14A	0.6 (10)	C17B—C12B—C13B—C14B	1.6 (10)
C11A—C12A—C13A—C14A	−178.6 (6)	C11B—C12B—C13B—C14B	−179.5 (7)
C12A—C13A—C14A—C15A	0.8 (11)	C12B—C13B—C14B—C15B	−1.4 (12)
C13A—C14A—C15A—C16A	−0.4 (11)	C13B—C14B—C15B—C16B	−0.1 (13)
C14A—C15A—C16A—C17A	−1.5 (10)	C14B—C15B—C16B—C17B	1.3 (12)
C13A—C12A—C17A—C16A	−2.6 (9)	C13B—C12B—C17B—C16B	−0.5 (10)
C11A—C12A—C17A—C16A	176.5 (6)	C11B—C12B—C17B—C16B	−179.2 (7)
C13A—C12A—C17A—Br2A	178.0 (5)	C13B—C12B—C17B—Br2B	−179.1 (5)
C11A—C12A—C17A—Br2A	−2.9 (8)	C11B—C12B—C17B—Br2B	2.2 (9)
C15A—C16A—C17A—C12A	3.1 (9)	C15B—C16B—C17B—C12B	−1.0 (11)
C15A—C16A—C17A—Br2A	−177.4 (5)	C15B—C16B—C17B—Br2B	177.6 (6)

Experimental details

Crystal data
Chemical formula	C₁₃H₈Br₂OS
M_r	372.07
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	34.524 (8), 3.9994 (9), 23.428 (5)
β (°)	126.804 (3)
V (Å³)	2590.1 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	6.40
Crystal size (mm)	0.22 × 0.15 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.228, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13574, 5988, 4266
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.109, 0.97
No. of reflections	5988
No. of parameters	308
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.44
Absolute structure	Flack (1983), 2846 Friedel pairs
Absolute structure parameter	0.000 (13)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), WinGX (Farrugia, 2012).

Acknowledgements

The authors thank Professor T. N. Guru Row, SSCU, IISc, Bangalore, for the data collection. SBV thanks the Acharya Nagarjuna University, Guntur, Andhrapradesh, India, for the support of a part-time PhD in Pharmacy.

References

Alex, G., Srinivasan, S., Krishnasamy, V., Suresh, R. V., Iyer, R. & Iyer, P. R. (1993). Acta Cryst. C49, 70–72. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, Z. & Su, G. (1993). Acta Cryst. C49, 1075–1077. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Liang, Y.-S., Mu, S., Wang, J.-Y. & Liu, D.-K. (2011). Acta Cryst. E67, o830. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Pascard, C. (1995). Acta Cryst. D51, 407–417. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, A. H., Robert, B. M., Richard, A. F., Hege, S. B., Leah, L. F., Thomas, W. P. & Jay, L. B. (2004). J. Med. Chem. 47, 1750–1759. Web of Science CrossRef PubMed Google Scholar