2-(Benzo[d]thia­zol-2-ylsulfon­yl)-1-(4-bromo­phen­yl)ethanone

Loghmani-Khouzani, H.; Hajiheidari, D.; Robinson, W.T.; Kia, R.

doi:10.1107/S1600536809053112

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o209

doi:10.1107/S1600536809053112

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2-(Benzo[d]thiazol-2-ylsulfonyl)-1-(4-bromophenyl)ethanone

Hossein Loghmani-Khouzani,^a ^* Dariush Hajiheidari,^a Ward T. Robinson ^b and Reza Kia ^c ‡

^aChemistry Department, University of Isfahan, Isfahan, 81746-73441, Iran, ^bUniversity of Malaya, Department of Chemistry, 50603, Kuala Lumpur, Malaysia, and ^cDepartment of Chemistry, Science and Research Campus, Islamic Azad University, Poonak, Tehran, Iran
^*Correspondence e-mail: loghmani_h@yahoo.com

(Received 9 December 2009; accepted 10 December 2009; online 19 December 2009)

In the title molecule, C₁₅H₁₀BrNO₃S₂, the dihedral angle between the benzothiazole ring system and the benzene ring is 67.57 (12)°. The crystal structure is stabilized by weak intermolecular C—H⋯O interactions. In addition, there is an intermolecular 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_r = 396.27
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.089
S = 1.03
2564 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.84 e Å⁻³

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⋯O2^iv	0.93	2.56	3.226 (4)	128
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053112/lh2971sup1.cif

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

checkCIF report

Comment top

The existence of so many valence states of sulfur has generated selective and novel ways to affect oxidation, dehydration, and carbon-carbon bond formation (Loghmani-Khouzani et al., 2008). Recent methods that allow introduction of a sulfur constituent β to a carbonyl group have shown particular promise (Loghmani-Khouzani et al., 2009a,b; Suryakiran et al., 2007; Munoz et al., 2005). 2-(1,3-Benzothiazol-2-yl-sulfonyl)-1-(4-bromophenyl)ethanone as a new compound with sulfur atom β to the carbonyl group is of great importance in organic synthesis. β-Keto-sulfones are a very important group of intermediates as they are precursors for Michael and Knoevenagel reactions (Marco et al., 1995) and are used in the preparation of acetylenes, allenes, chalcones, vinyl sulfones, polyfunctionalized 4H-pyrans and ketones (Fuju et al., 1988). In addition, β-keto-sulfones can be converted into optically active β-hydroxy-sulfones, halomethyl sulfones and dihalomethyl sulfones (Ni et al., 2006). Halomethyl sulfones and dihalomethyl sulfones are very good α-carbanion stabilizing substituents and precursors for the preparation of alkenes, aziridines, epoxides, and β-hydroxy-sulfones (Grossert et al., 1984). Haloalkyl sulfones are useful in preventing aquatic organisms from attaching to fishing nets and ship hulls (Oishi et al., 1988). They also possess other biological properties such as herbicidal, bactericidal antifungal, algaecidal and insecticidal (Antane et al., 2004). Recently sulfone-linked heterocycles were prepared and have been showed antimicrobial activity (Padmavathi et al., 2008). We report here the crystal structure of the title compound as a precursor for synthesis of gem-difluoromethylene-containing heterocycle.

In the molecule of the title compound, (Fig. 1), a new thio-benzothiazole derivative, the bond lengths (Allen et al., 1987) and angles are within the normal values and are comparable to the related structures (Loghmani-Khouzani et al., 2008a,b). The dihedral angle between the benzothiazole ring system and the benzene ring is 67.57 (12)°. An interesting feature of the crystal structure is the short intermolecular Br···C^iv [3.379 (3) Å; (iv) -x, -y, 2 - z] contact which is shorter than the sum of the van der Waals radii of these atoms. The crystal structure is stabilized by weak intermolecular C—H···O interactions (Table 1, Fig. 2).

Related literature top

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 top

Sodium carbonate (4.5 mmol) was added to a stirred solution of 2-mercaptobenzothiazol (3 mmol) in ethanol (15 mL) and water (15 mL) and stirred at room temperature for 30 min. 2-bromo-1- (4-bromophenyl)ethanone (3 mmol) was added to the reaction mixture and stirring was continued for 1 h. The reaction was monitored by TLC and after 60 min. showed the complete disappearance of starting materials. The reaction mixture was poured into 100 mL of 1 M HCl containing 50 g of crushed ice. The product was filtered under vacuum and the filtrate was washed with 10 mL ice-cold ethanol and 10 mL water. Recrystallization from petroleum ether and filtration gave 2-(Benzo[d]thiazol-2-ylthio)-1-(4-bromophenyl)ethanone. The product yield was 96%. For oxidation of the resulting Product, m-CPBA (3 mmol) was added to a solution of 2-(1,3-Benzothiazol-2- yl-thio)-1-(4-bromophenyl)ethanone (1 mmol) in CH₂Cl₂ (20 mL) under stirring at 273K. The mixture was stirred at room temperature for 1 h to complete the reaction. Saturated aqueous sodium sulfite solution (50 mL) was added and the mixture was stirred for a further 1 h at room temperature. The CH₂Cl₂ layer was washed with water (50 mL), dried (MgSO₄), filtered, and concentrated under reduced pressure. Flash chromatography on silica gel using AcOEt/petroleum ether (30:70) afforded 2-(1,3-Benzothiazol-2-ylsulfonyl)-1-(4-bromophenyl) ethanone. The product yield of the resulted β-ketosulfone was 80 %. White solid; m.p.: 196-198 ^°C; ¹H-NMR (400 MHz; CDCl₃): δ 8.16-7.47 (m, 8H), 5.67 (s, 2H). ¹³C-NMR (126 MHz; CDCl₃): δ 188.1 (C=O), 154.1, 151.5, 134.8, 133.2, 129.7, 129.1, 126.2, 123.9, 123.1, 121.7, 121.2, 59.8. IR (KBr, cm^-1 ): 3010, 2800, 1684 (C=O), 1570, 1401, 1328, 1150, 1122, 970, 803, 752. Anal. Calcd for C₁₅H₁₀BrNO₃S₂: C, 45.46; H, 2.54; N, 3.53. Found: C, 45.49; H, 2.50; N, 3.43.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. Part of the crystal structure of the title compound, viewed approximately along the a-axis, showing molecules connected via weak intermolecular C—H···O interactions. Intermolecular interactions are drawn as dashed lines.

2-(Benzo[d]thiazol-2-ylsulfonyl)-1-(4-bromophenyl)ethanone top

Crystal data top

C₁₅H₁₀BrNO₃S₂	F(000) = 792
M_r = 396.27	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0547P)²] where P = (F_o² + 2F_c²)/3
2564 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

C₁₅H₁₀BrNO₃S₂	V = 1482.2 (5) Å³
M_r = 396.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.6695 (10) Å	µ = 3.07 mm⁻¹
b = 24.489 (4) Å	T = 296 K
c = 10.7042 (19) Å	0.42 × 0.30 × 0.05 mm
β = 94.178 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2564 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2140 reflections with I > 2σ(I)
T_min = 0.363, T_max = 0.864	R_int = 0.038
6602 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.03	Δρ_max = 0.65 e Å⁻³
2564 reflections	Δρ_min = −0.84 e Å⁻³
199 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.93	2.56	3.226 (4)	128

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x, −y+1, −z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrNO₃S₂
M_r	396.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.6695 (10), 24.489 (4), 10.7042 (19)
β (°)	94.178 (3)
V (Å³)	1482.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.07
Crystal size (mm)	0.42 × 0.30 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.363, 0.864
No. of measured, independent and observed [I > 2σ(I)] reflections	6602, 2564, 2140
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.089, 1.03
No. of reflections	2564
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.84

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O2ⁱ	0.93	2.56	3.420 (4)	154.0
C8—H8A···O1ⁱⁱ	0.97	2.37	3.289 (3)	157.7
C8—H8B···O1ⁱⁱⁱ	0.97	2.50	3.241 (4)	132.8
C14—H14A···O2^iv	0.93	2.56	3.226 (4)	128.4

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x, −y+1, −z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z.

Footnotes

‡Additional corresponding author: zsrkk@yahoo.com Thomson Reuters Researcher ID: A-5471-2009

Acknowledgements

We thank the University of Isfahan and the University of Malaya for supporting this work.

References

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