1-(5-Bromo-4-phenyl-1,3-thia­zol-2-yl)pyrrolidin-2-one

Ghabbour, H.A.; Kadi, A.A.; El-Subbagh, H.I.; Chia, T.S.; Fun, H.-K.

doi:10.1107/S160053681201954X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1738-o1739

doi:10.1107/S160053681201954X

Open

access

1-(5-Bromo-4-phenyl-1,3-thiazol-2-yl)pyrrolidin-2-one

Hazem A. Ghabbour,^a Adnan A. Kadi,^a Hussein I. El-Subbagh,^b Tze Shyang Chia ^c and Hoong-Kun Fun ^c ^*‡

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences and Pharmaceutical Industries, Future University, Cairo 12311, Egypt, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 28 April 2012; accepted 1 May 2012; online 16 May 2012)

The asymmetric unit of the title compound, C₁₃H₁₁BrN₂OS, consists of two crystallographically independent molecules (A and B). In each molecule, the pyrrolidine ring adopts an envelope conformation with a methylene C atom as the flap atom. In molecule A, the central thiazole ring makes a dihedral angle of 36.69 (11)° with the adjacent phenyl ring, whereas the corresponding angle is 36.85 (12)° in molecule B. The pyrrolidine ring is slightly twisted from the thiazole ring, with C—N—C—N torsion angles of 4.8 (3) and 3.0 (4)° in molecules A and B, respectively. In the crystal, C—H⋯π and π–π [centroid-to-centroid distance = 3.7539 (14) Å] interactions are observed. The crystal studied was a pseudo-merohedral twin with twin law (-100 0-10 101) and a refined component ratio of 0.7188 (5):0.2812 (5).

Related literature

For background to thiazoles, see: Bishayee et al. (1997 ); Chitamber & Wereley (1997 ); Bhaskar et al. (2008 ); Sharma et al. (2009 ); Bhattacharya et al. (2005 ); Spector et al. (1998 ). For ring-puckering parameters, see: Cremer & Pople (1975 ). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₁BrN₂OS
M_r = 323.21
Monoclinic, P 2₁
a = 7.5243 (3) Å
b = 14.1861 (6) Å
c = 12.4488 (6) Å
β = 107.508 (1)°
V = 1267.23 (10) Å³
Z = 4
Mo Kα radiation
μ = 3.40 mm⁻¹
T = 100 K
0.26 × 0.14 × 0.14 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.466, T_max = 0.646
30838 measured reflections
9338 independent reflections
8701 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.051
S = 0.99
9338 reflections
326 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.46 e Å⁻³
Absolute structure: Flack (1983 ), with 4219 Friedel pairs
Flack parameter: 0.017 (4)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1B–C6B ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12A—H12B⋯Cg1ⁱ	0.97	2.89	3.767 (3)	151
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201954X/is5131sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201954X/is5131Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201954X/is5131Isup3.cml

checkCIF report

Comment top

Thiazole is a five-membered ring system with two hetero atoms (S, N) placed at the 1 and 3 positions of the heterocycle. The nucleus is a building block in the structure of various natural products and biologically active compounds, like thiamine (vitamin-B), also in some antibiotics drugs like penicillin, micrococcin and many metabolic products of fungi and primitive marine animals (Bhaskar et al., 2008). Thiazole-containing drugs have widespread use in a variety of medical conditions such as fungal and bacterial infections, gastric ulcers, cancer, etc (Bishayee et al., 1997). Thiazole derivatives are involved frequently as the subject of drug design and synthesis efforts and they are reported to possess several activities like antibacterial, antifungal, anti-inflammatory (Sharma et al., 2009), analgesic, antitubercular, central nervous system (CNS) stimmulant activity as well as anti-HIV activity (Bhattacharya et al., 2005). Aminothiazole derivatives are well explored as agents of potential biological activities and some of the derivatives of thiazoles have shown inhibition towards herpes simplex virus (Spector et al., 1998).

The asymmetric unit of the title compound (Fig. 1) consists of two crystallographically independent molecules (A and B). In both molecules, the pyrrolidine ring (N2/C10–C13) adopts an envelope conformation with atom C11 as the flap atom [puckering parameters (Cremer & Pople, 1975), Q = 0.272 (3) Å and ϕ = 254.4 (5)° in molecule A; Q = 0.282 (3) Å and ϕ = 74.7 (5)° in molecule B]. In molecule A, the central thiazole ring (S1/N1/C7–C9) makes a dihedral angle of 36.69 (11)° with the adjacent benzene ring (C1–C6), whereas the corresponding angle is 36.85 (12)° in molecule B. The pyrrolidine ring is slightly twisted from the thiazole ring with C10—N2—C9—N1 torsion angles of 4.8 (3) and 3.0 (4)° in molecules A and B, respectively.

In the crystal packing, no significant intermoelcular hydrogen bondings are observed. The crystal packing is stabilized by C—H···Cg1 and π—π [Cg2—Cg3 = 3.7539 (14) Å; symmetry code = 1-X,1/2+Y,1-Z] interactions, where Cg1, Cg2 and Cg3 are the centroids of C1B–C6B, S1A/N1A/C7A–C9A and S1B/N1B/C7B–C9B rings, respectively.

Related literature top

For background literature, see: Bishayee et al. (1997); Chitamber & Wereley (1997); Bhaskar et al. (2008); Sharma et al. (2009); Bhattacharya et al. (2005); Spector et al. (1998). For ring-puckering parameters, see: Cremer & Pople (1975). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

4-Chlorobutanoyl chloride (423 mg, 3 mmol) was added dropwise to a solution of 5-bromo-4-phenylthiazol-2-amine (255 mg, 1 mmol) and K₂CO₃ (414 mg, 3 mmol) in CHCl₃. The mixture was stirred for 48 h at room temperature and then ammonia and water were added to remove excess 4-chlorobutanoyl chloride and K₂CO₃. The organic solvent was removed in vacuum. The residue was taken up in dry toluene and the solution was refluxed for 10 h after addition of excess amount of piperidine. The mixture was cooled and the solvent was removed in vacuum to give solid which was then purified by chromatotron and crystallized from ethanol to give the single crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The asymmetric unit of the title compound with atom labels and 50% probability displacement ellipsoids.

1-(5-Bromo-4-phenyl-1,3-thiazol-2-yl)pyrrolidin-2-one top

Crystal data top

C₁₃H₁₁BrN₂OS	F(000) = 648
M_r = 323.21	D_x = 1.694 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9880 reflections
a = 7.5243 (3) Å	θ = 2.2–32.0°
b = 14.1861 (6) Å	µ = 3.40 mm⁻¹
c = 12.4488 (6) Å	T = 100 K
β = 107.508 (1)°	Block, colourless
V = 1267.23 (10) Å³	0.26 × 0.14 × 0.14 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	9338 independent reflections
Radiation source: fine-focus sealed tube	8701 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 33.6°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.466, T_max = 0.646	k = −21→21
30838 measured reflections	l = −19→19

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)] = 0.027	H-atom parameters constrained
wR(F²) = 0.051	w = 1/[σ²(F_o²) + (0.0136P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
9338 reflections	Δρ_max = 0.58 e Å⁻³
326 parameters	Δρ_min = −0.46 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 4219 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.017 (4)

Crystal data top

C₁₃H₁₁BrN₂OS	V = 1267.23 (10) Å³
M_r = 323.21	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 7.5243 (3) Å	µ = 3.40 mm⁻¹
b = 14.1861 (6) Å	T = 100 K
c = 12.4488 (6) Å	0.26 × 0.14 × 0.14 mm
β = 107.508 (1)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	9338 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	8701 reflections with I > 2σ(I)
T_min = 0.466, T_max = 0.646	R_int = 0.032
30838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.051	Δρ_max = 0.58 e Å⁻³
S = 0.99	Δρ_min = −0.46 e Å⁻³
9338 reflections	Absolute structure: Flack (1983), with 4219 Friedel pairs
326 parameters	Absolute structure parameter: 0.017 (4)
1 restraint

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1A	1.01261 (3)	0.351681 (14)	0.70723 (2)	0.02637 (6)
S1A	0.68748 (7)	0.33990 (4)	0.48703 (5)	0.01897 (10)
O1A	0.4724 (3)	0.32508 (11)	0.26929 (13)	0.0249 (3)
N1A	0.4385 (2)	0.34234 (16)	0.59269 (14)	0.0167 (3)
N2A	0.3089 (3)	0.33380 (14)	0.39687 (16)	0.0189 (4)
C1A	0.7366 (3)	0.39986 (15)	0.87748 (19)	0.0214 (4)
H1AA	0.8276	0.4358	0.8601	0.026*
C2A	0.7282 (3)	0.39718 (17)	0.98699 (19)	0.0243 (5)
H2AA	0.8110	0.4331	1.0423	0.029*
C3A	0.5979 (3)	0.34160 (19)	1.01478 (19)	0.0246 (5)
H3AA	0.5954	0.3389	1.0890	0.030*
C4A	0.4701 (3)	0.28953 (17)	0.93178 (19)	0.0225 (4)
H4AA	0.3815	0.2524	0.9501	0.027*
C5A	0.4761 (3)	0.29351 (16)	0.82224 (18)	0.0179 (4)
H5AA	0.3905	0.2590	0.7667	0.022*
C6A	0.6091 (3)	0.34881 (16)	0.79332 (17)	0.0162 (4)
C7A	0.6099 (3)	0.34893 (16)	0.67534 (17)	0.0167 (4)
C8A	0.7554 (3)	0.34945 (18)	0.63183 (17)	0.0176 (4)
C9A	0.4600 (3)	0.33758 (15)	0.49273 (18)	0.0166 (4)
C10A	0.1169 (3)	0.34222 (19)	0.40144 (19)	0.0225 (4)
H10A	0.0897	0.4061	0.4195	0.027*
H10B	0.0937	0.2992	0.4563	0.027*
C11A	0.0021 (4)	0.31523 (16)	0.2810 (2)	0.0244 (5)
H11A	−0.1123	0.3515	0.2568	0.029*
H11B	−0.0288	0.2487	0.2762	0.029*
C12A	0.1303 (3)	0.33887 (18)	0.20894 (19)	0.0267 (5)
H12A	0.1118	0.2946	0.1471	0.032*
H12B	0.1068	0.4022	0.1786	0.032*
C13A	0.3242 (3)	0.33079 (14)	0.28908 (19)	0.0212 (4)
Br1B	0.15444 (3)	0.079853 (14)	0.69491 (2)	0.02544 (5)
S1B	0.24659 (7)	0.09024 (4)	0.46979 (4)	0.01913 (10)
O1B	0.2343 (3)	0.11605 (13)	0.25040 (14)	0.0269 (4)
N1B	0.6031 (2)	0.08191 (17)	0.56770 (14)	0.0179 (3)
N2B	0.5265 (3)	0.09060 (15)	0.37119 (14)	0.0191 (3)
C1B	0.5995 (3)	0.02734 (16)	0.85721 (18)	0.0220 (4)
H1BA	0.4904	−0.0079	0.8416	0.026*
C2B	0.7207 (4)	0.03050 (17)	0.96597 (19)	0.0253 (5)
H2BA	0.6929	−0.0037	1.0226	0.030*
C3B	0.8816 (3)	0.0835 (2)	0.99154 (18)	0.0260 (5)
H3BA	0.9604	0.0860	1.0651	0.031*
C4B	0.9255 (3)	0.13339 (18)	0.9064 (2)	0.0234 (5)
H4BA	1.0339	0.1692	0.9229	0.028*
C5B	0.8065 (3)	0.12933 (17)	0.79710 (18)	0.0188 (4)
H5BA	0.8372	0.1619	0.7403	0.023*
C6B	0.6420 (3)	0.07735 (17)	0.77091 (17)	0.0167 (4)
C7B	0.5198 (3)	0.07758 (17)	0.65372 (15)	0.0160 (3)
C8B	0.3295 (3)	0.0800 (2)	0.61500 (18)	0.0194 (4)
C9B	0.4773 (3)	0.08761 (18)	0.47029 (16)	0.0170 (4)
C10B	0.7195 (3)	0.0830 (2)	0.37033 (17)	0.0212 (4)
H10C	0.7822	0.0302	0.4157	0.025*
H10D	0.7884	0.1404	0.3975	0.025*
C11B	0.6969 (4)	0.06701 (18)	0.2457 (2)	0.0272 (5)
H11C	0.7981	0.0963	0.2246	0.033*
H11D	0.6946	0.0002	0.2287	0.033*
C12B	0.5114 (4)	0.11300 (18)	0.18401 (19)	0.0242 (5)
H12C	0.5289	0.1781	0.1657	0.029*
H12D	0.4496	0.0793	0.1151	0.029*
C13B	0.4007 (3)	0.10679 (15)	0.2667 (2)	0.0219 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.01407 (9)	0.02869 (12)	0.03443 (13)	−0.00219 (9)	0.00438 (9)	0.00372 (11)
S1A	0.0193 (2)	0.0182 (2)	0.0212 (2)	0.0000 (2)	0.00885 (19)	0.0019 (2)
O1A	0.0317 (9)	0.0245 (8)	0.0207 (7)	−0.0017 (7)	0.0111 (7)	0.0014 (6)
N1A	0.0130 (8)	0.0190 (9)	0.0170 (8)	0.0014 (7)	0.0028 (6)	0.0004 (7)
N2A	0.0210 (9)	0.0174 (9)	0.0172 (8)	0.0011 (7)	0.0040 (7)	−0.0007 (7)
C1A	0.0223 (11)	0.0151 (9)	0.0232 (10)	−0.0031 (8)	0.0016 (9)	0.0011 (8)
C2A	0.0289 (12)	0.0215 (10)	0.0162 (10)	0.0000 (9)	−0.0029 (9)	−0.0020 (8)
C3A	0.0295 (11)	0.0239 (11)	0.0185 (10)	0.0055 (10)	0.0042 (9)	0.0003 (10)
C4A	0.0231 (11)	0.0249 (10)	0.0208 (11)	0.0014 (9)	0.0084 (9)	−0.0008 (9)
C5A	0.0158 (9)	0.0199 (10)	0.0170 (10)	−0.0001 (7)	0.0032 (8)	−0.0018 (7)
C6A	0.0134 (8)	0.0172 (9)	0.0162 (8)	0.0039 (8)	0.0015 (7)	0.0023 (8)
C7A	0.0154 (8)	0.0143 (8)	0.0186 (9)	−0.0006 (8)	0.0023 (7)	0.0007 (8)
C8A	0.0133 (8)	0.0187 (9)	0.0193 (9)	−0.0007 (9)	0.0024 (7)	0.0020 (9)
C9A	0.0151 (9)	0.0164 (8)	0.0171 (9)	0.0017 (8)	0.0031 (8)	0.0013 (7)
C10A	0.0180 (10)	0.0251 (11)	0.0212 (10)	0.0043 (9)	0.0013 (8)	−0.0024 (9)
C11A	0.0264 (12)	0.0250 (9)	0.0191 (10)	0.0000 (9)	0.0031 (9)	−0.0020 (9)
C12A	0.0322 (13)	0.0242 (11)	0.0193 (10)	−0.0004 (10)	0.0008 (9)	0.0020 (9)
C13A	0.0292 (11)	0.0148 (9)	0.0180 (9)	0.0006 (8)	0.0047 (10)	0.0016 (7)
Br1B	0.02277 (10)	0.02499 (10)	0.03492 (12)	−0.00498 (9)	0.01830 (9)	−0.00685 (11)
S1B	0.0166 (2)	0.0177 (2)	0.0224 (2)	0.0005 (2)	0.00493 (19)	−0.0016 (2)
O1B	0.0266 (9)	0.0261 (8)	0.0232 (8)	0.0029 (7)	0.0002 (7)	−0.0029 (7)
N1B	0.0194 (8)	0.0191 (7)	0.0175 (7)	0.0016 (9)	0.0092 (6)	0.0007 (8)
N2B	0.0216 (9)	0.0206 (8)	0.0159 (7)	0.0007 (8)	0.0068 (7)	0.0003 (7)
C1B	0.0279 (11)	0.0214 (10)	0.0198 (10)	−0.0028 (9)	0.0117 (9)	−0.0028 (8)
C2B	0.0368 (13)	0.0242 (11)	0.0183 (11)	0.0021 (9)	0.0134 (10)	−0.0002 (8)
C3B	0.0294 (12)	0.0310 (11)	0.0174 (9)	0.0074 (12)	0.0067 (8)	−0.0033 (11)
C4B	0.0180 (10)	0.0266 (11)	0.0262 (12)	0.0014 (9)	0.0075 (9)	−0.0016 (9)
C5B	0.0176 (10)	0.0220 (11)	0.0191 (10)	0.0051 (8)	0.0089 (9)	0.0024 (8)
C6B	0.0214 (9)	0.0134 (8)	0.0182 (9)	0.0021 (9)	0.0104 (7)	−0.0008 (9)
C7B	0.0190 (8)	0.0132 (7)	0.0189 (8)	0.0000 (8)	0.0105 (7)	0.0000 (8)
C8B	0.0200 (9)	0.0165 (8)	0.0246 (10)	−0.0014 (9)	0.0113 (8)	−0.0022 (10)
C9B	0.0171 (9)	0.0168 (8)	0.0178 (9)	0.0027 (8)	0.0061 (7)	0.0037 (9)
C10B	0.0200 (10)	0.0269 (10)	0.0168 (9)	−0.0025 (11)	0.0058 (7)	−0.0016 (11)
C11B	0.0349 (13)	0.0291 (13)	0.0215 (10)	−0.0019 (10)	0.0146 (10)	−0.0015 (9)
C12B	0.0358 (13)	0.0206 (10)	0.0168 (10)	0.0016 (10)	0.0086 (9)	−0.0012 (8)
C13B	0.0285 (12)	0.0156 (10)	0.0195 (10)	0.0018 (8)	0.0042 (9)	−0.0019 (7)

Geometric parameters (Å, º) top

Br1A—C8A	1.880 (2)	Br1B—C8B	1.874 (2)
S1A—C8A	1.725 (2)	S1B—C8B	1.732 (2)
S1A—C9A	1.7349 (19)	S1B—C9B	1.734 (2)
O1A—C13A	1.214 (3)	O1B—C13B	1.214 (3)
N1A—C9A	1.304 (3)	N1B—C9B	1.297 (3)
N1A—C7A	1.390 (3)	N1B—C7B	1.395 (2)
N2A—C9A	1.379 (3)	N2B—C13B	1.379 (3)
N2A—C13A	1.381 (3)	N2B—C9B	1.391 (3)
N2A—C10A	1.468 (3)	N2B—C10B	1.460 (3)
C1A—C2A	1.384 (3)	C1B—C2B	1.387 (3)
C1A—C6A	1.392 (3)	C1B—C6B	1.402 (3)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.381 (4)	C2B—C3B	1.379 (4)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.393 (3)	C3B—C4B	1.393 (4)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.379 (3)	C4B—C5B	1.387 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.401 (3)	C5B—C6B	1.393 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.471 (3)	C6B—C7B	1.472 (3)
C7A—C8A	1.360 (3)	C7B—C8B	1.367 (3)
C10A—C11A	1.536 (3)	C10B—C11B	1.526 (3)
C10A—H10A	0.9700	C10B—H10C	0.9700
C10A—H10B	0.9700	C10B—H10D	0.9700
C11A—C12A	1.539 (4)	C11B—C12B	1.522 (4)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—C13A	1.504 (3)	C12B—C13B	1.509 (4)
C12A—H12A	0.9700	C12B—H12C	0.9700
C12A—H12B	0.9700	C12B—H12D	0.9700

C8A—S1A—C9A	86.83 (10)	C8B—S1B—C9B	87.07 (10)
C9A—N1A—C7A	110.89 (17)	C9B—N1B—C7B	110.50 (17)
C9A—N2A—C13A	123.6 (2)	C13B—N2B—C9B	123.5 (2)
C9A—N2A—C10A	121.85 (18)	C13B—N2B—C10B	114.04 (18)
C13A—N2A—C10A	114.25 (19)	C9B—N2B—C10B	122.35 (17)
C2A—C1A—C6A	120.1 (2)	C2B—C1B—C6B	119.8 (2)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	120.1
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	120.1
C3A—C2A—C1A	120.6 (2)	C3B—C2B—C1B	121.1 (2)
C3A—C2A—H2AA	119.7	C3B—C2B—H2BA	119.4
C1A—C2A—H2AA	119.7	C1B—C2B—H2BA	119.4
C2A—C3A—C4A	120.1 (2)	C2B—C3B—C4B	119.6 (2)
C2A—C3A—H3AA	120.0	C2B—C3B—H3BA	120.2
C4A—C3A—H3AA	120.0	C4B—C3B—H3BA	120.2
C5A—C4A—C3A	119.4 (2)	C5B—C4B—C3B	119.6 (2)
C5A—C4A—H4AA	120.3	C5B—C4B—H4BA	120.2
C3A—C4A—H4AA	120.3	C3B—C4B—H4BA	120.2
C4A—C5A—C6A	121.0 (2)	C4B—C5B—C6B	121.2 (2)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.4
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.4
C1A—C6A—C5A	118.8 (2)	C5B—C6B—C1B	118.7 (2)
C1A—C6A—C7A	122.8 (2)	C5B—C6B—C7B	118.49 (19)
C5A—C6A—C7A	118.37 (19)	C1B—C6B—C7B	122.8 (2)
C8A—C7A—N1A	112.61 (18)	C8B—C7B—N1B	113.14 (17)
C8A—C7A—C6A	130.06 (18)	C8B—C7B—C6B	128.69 (17)
N1A—C7A—C6A	117.22 (18)	N1B—C7B—C6B	118.04 (17)
C7A—C8A—S1A	113.25 (15)	C7B—C8B—S1B	112.33 (15)
C7A—C8A—Br1A	129.24 (16)	C7B—C8B—Br1B	129.92 (16)
S1A—C8A—Br1A	117.40 (11)	S1B—C8B—Br1B	117.67 (11)
N1A—C9A—N2A	121.45 (18)	N1B—C9B—N2B	121.12 (18)
N1A—C9A—S1A	116.41 (15)	N1B—C9B—S1B	116.93 (15)
N2A—C9A—S1A	122.11 (16)	N2B—C9B—S1B	121.95 (15)
N2A—C10A—C11A	102.29 (19)	N2B—C10B—C11B	102.22 (17)
N2A—C10A—H10A	111.3	N2B—C10B—H10C	111.3
C11A—C10A—H10A	111.3	C11B—C10B—H10C	111.3
N2A—C10A—H10B	111.3	N2B—C10B—H10D	111.3
C11A—C10A—H10B	111.3	C11B—C10B—H10D	111.3
H10A—C10A—H10B	109.2	H10C—C10B—H10D	109.2
C10A—C11A—C12A	104.3 (2)	C12B—C11B—C10B	104.71 (19)
C10A—C11A—H11A	110.9	C12B—C11B—H11C	110.8
C12A—C11A—H11A	110.9	C10B—C11B—H11C	110.8
C10A—C11A—H11B	110.9	C12B—C11B—H11D	110.8
C12A—C11A—H11B	110.9	C10B—C11B—H11D	110.8
H11A—C11A—H11B	108.9	H11C—C11B—H11D	108.9
C13A—C12A—C11A	104.47 (19)	C13B—C12B—C11B	103.98 (18)
C13A—C12A—H12A	110.9	C13B—C12B—H12C	111.0
C11A—C12A—H12A	110.9	C11B—C12B—H12C	111.0
C13A—C12A—H12B	110.9	C13B—C12B—H12D	111.0
C11A—C12A—H12B	110.9	C11B—C12B—H12D	111.0
H12A—C12A—H12B	108.9	H12C—C12B—H12D	109.0
O1A—C13A—N2A	123.3 (2)	O1B—C13B—N2B	123.8 (2)
O1A—C13A—C12A	129.6 (2)	O1B—C13B—C12B	129.3 (2)
N2A—C13A—C12A	107.1 (2)	N2B—C13B—C12B	106.9 (2)

C6A—C1A—C2A—C3A	2.2 (3)	C6B—C1B—C2B—C3B	1.2 (4)
C1A—C2A—C3A—C4A	−1.7 (4)	C1B—C2B—C3B—C4B	−1.3 (4)
C2A—C3A—C4A—C5A	0.5 (4)	C2B—C3B—C4B—C5B	0.2 (4)
C3A—C4A—C5A—C6A	0.2 (3)	C3B—C4B—C5B—C6B	1.0 (3)
C2A—C1A—C6A—C5A	−1.4 (3)	C4B—C5B—C6B—C1B	−1.1 (3)
C2A—C1A—C6A—C7A	179.7 (2)	C4B—C5B—C6B—C7B	178.7 (2)
C4A—C5A—C6A—C1A	0.2 (3)	C2B—C1B—C6B—C5B	0.0 (3)
C4A—C5A—C6A—C7A	179.1 (2)	C2B—C1B—C6B—C7B	−179.8 (2)
C9A—N1A—C7A—C8A	0.4 (3)	C9B—N1B—C7B—C8B	0.3 (3)
C9A—N1A—C7A—C6A	−176.2 (2)	C9B—N1B—C7B—C6B	−175.9 (2)
C1A—C6A—C7A—C8A	38.0 (4)	C5B—C6B—C7B—C8B	−141.2 (3)
C5A—C6A—C7A—C8A	−140.9 (3)	C1B—C6B—C7B—C8B	38.6 (4)
C1A—C6A—C7A—N1A	−146.1 (2)	C5B—C6B—C7B—N1B	34.3 (3)
C5A—C6A—C7A—N1A	35.1 (3)	C1B—C6B—C7B—N1B	−145.9 (2)
N1A—C7A—C8A—S1A	−1.0 (3)	N1B—C7B—C8B—S1B	−1.3 (3)
C6A—C7A—C8A—S1A	175.1 (2)	C6B—C7B—C8B—S1B	174.4 (2)
N1A—C7A—C8A—Br1A	−176.95 (19)	N1B—C7B—C8B—Br1B	−177.9 (2)
C6A—C7A—C8A—Br1A	−0.8 (4)	C6B—C7B—C8B—Br1B	−2.2 (4)
C9A—S1A—C8A—C7A	0.9 (2)	C9B—S1B—C8B—C7B	1.4 (2)
C9A—S1A—C8A—Br1A	177.41 (16)	C9B—S1B—C8B—Br1B	178.51 (17)
C7A—N1A—C9A—N2A	−177.8 (2)	C7B—N1B—C9B—N2B	−178.5 (2)
C7A—N1A—C9A—S1A	0.3 (3)	C7B—N1B—C9B—S1B	0.9 (3)
C13A—N2A—C9A—N1A	178.5 (2)	C13B—N2B—C9B—N1B	−172.8 (2)
C10A—N2A—C9A—N1A	4.8 (3)	C10B—N2B—C9B—N1B	3.0 (4)
C13A—N2A—C9A—S1A	0.5 (3)	C13B—N2B—C9B—S1B	7.8 (3)
C10A—N2A—C9A—S1A	−173.23 (18)	C10B—N2B—C9B—S1B	−176.4 (2)
C8A—S1A—C9A—N1A	−0.7 (2)	C8B—S1B—C9B—N1B	−1.4 (2)
C8A—S1A—C9A—N2A	177.4 (2)	C8B—S1B—C9B—N2B	178.1 (2)
C9A—N2A—C10A—C11A	−169.7 (2)	C13B—N2B—C10B—C11B	−16.4 (3)
C13A—N2A—C10A—C11A	16.0 (3)	C9B—N2B—C10B—C11B	167.4 (2)
N2A—C10A—C11A—C12A	−25.5 (2)	N2B—C10B—C11B—C12B	26.6 (3)
C10A—C11A—C12A—C13A	26.6 (2)	C10B—C11B—C12B—C13B	−27.8 (3)
C9A—N2A—C13A—O1A	4.9 (3)	C9B—N2B—C13B—O1B	−3.2 (4)
C10A—N2A—C13A—O1A	179.1 (2)	C10B—N2B—C13B—O1B	−179.3 (2)
C9A—N2A—C13A—C12A	−173.4 (2)	C9B—N2B—C13B—C12B	175.1 (2)
C10A—N2A—C13A—C12A	0.8 (3)	C10B—N2B—C13B—C12B	−1.0 (3)
C11A—C12A—C13A—O1A	164.4 (2)	C11B—C12B—C13B—O1B	−163.6 (2)
C11A—C12A—C13A—N2A	−17.4 (2)	C11B—C12B—C13B—N2B	18.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1B–C6B ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12A—H12B···Cg1ⁱ	0.97	2.89	3.767 (3)	151

Symmetry code: (i) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁BrN₂OS
M_r	323.21
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	7.5243 (3), 14.1861 (6), 12.4488 (6)
β (°)	107.508 (1)
V (Å³)	1267.23 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.40
Crystal size (mm)	0.26 × 0.14 × 0.14

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.466, 0.646
No. of measured, independent and observed [I > 2σ(I)] reflections	30838, 9338, 8701
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.778

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.051, 0.99
No. of reflections	9338
No. of parameters	326
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.46
Absolute structure	Flack (1983), with 4219 Friedel pairs
Absolute structure parameter	0.017 (4)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1B–C6B ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12A—H12B···Cg1ⁱ	0.97	2.89	3.767 (3)	151

Symmetry code: (i) −x+1, y+1/2, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HAG and AAK thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and TSC thank Universiti Sains Malaysia (USM) for a Research University grant (No. 1001/PFIZIK/811160). TSC thanks the Malaysian government and USM for the award of a Research Fellowship.

References

Bhaskar, V. H., Kumar, M., Sangameswaran, B. & Balakrishnan, B. R. (2008). Rasayan J. Chem. 1, 218–223. CAS Google Scholar
Bhattacharya, P., Leonard, J. T. & Roy, K. (2005). Bioorg. Med. Chem. 13, 1159–1165. Web of Science CrossRef PubMed CAS Google Scholar
Bishayee, A., Karmaker, R., Mandal, A., Kundu, S. N. & Chaterjee, M. (1997). Eur. J. Cancer Prev. 6, 58–70. CrossRef CAS PubMed Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chitamber, C. R. & Wereley, J. P. (1997). J. Biol. Chem. 272, 12151–12157. PubMed Web of Science Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sharma, R. N., Xavier, F. P., Vasu, K. K., Chaturvedi, S. C. & Pancholi, S. S. (2009). J. Enzyme Inhib. Med. Chem. 24, 890–897. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spector, F. C., Liang, L., Giordano, H., Sivaraja, M. & Peterson, M. G. (1998). J. Virol. 72, 6979–6987. Web of Science CAS PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1738-o1739

doi:10.1107/S160053681201954X

Open

access