7-Bromo-3,3-dibutyl-8-meth­oxy-2,3-di­hydro-1,5-benzothia­zepin-4(5H)-one

Deepu, C.V.; Manjula, M.; Pampa, K.J.; Bhadregowda, D.G.; Lokanath, N.K.

doi:10.1107/S1600536813013238

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1129

https://doi.org/10.1107/S1600536813013238

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7-Bromo-3,3-dibutyl-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

C. V. Deepu,^a M. Manjula,^b K. J. Pampa,^c D. G. Bhadregowda ^a ^* and N. K. Lokanath ^b

^aDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 006, India, ^bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^cDepartment of Studies in Microbiology, Manasagangotri, University of Mysore, Mysore 570 006, India
^*Correspondence e-mail: bhadre_chem@rediffmail.com

(Received 7 May 2013; accepted 14 May 2013; online 19 June 2013)

In the title compound C₁₈H₂₆BrNO₂S, the thiazepine ring adopts a boat conformation. The dihedral angle between the mean planes through the benzene ring and the four C atoms making up the basal plane of the boat is 35.8 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops.

Related literature

For reference bond lengths, see: Allen et al. (1987 ). For background to the uses of this class of compounds, see: Fedi et al. (2008 ); Ganesh et al. (2011 ); Riedel et al. (2007 ).

Experimental

Crystal data

C₁₈H₂₆BrNO₂S
M_r = 400.30
Monoclinic, P 2₁ /n
a = 7.7844 (18) Å
b = 11.251 (2) Å
c = 22.039 (6) Å
β = 98.199 (8)°
V = 1910.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.27 mm⁻¹
T = 100 K
0.32 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
16056 measured reflections
4662 independent reflections
2750 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.141
S = 1.03
4662 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14⋯O15ⁱ	0.86	2.13	2.985 (3)	175
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: Mercury.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813013238/hb7081sup1.cif

Structure factors: contains datablock mm. DOI: https://doi.org/10.1107/S1600536813013238/hb7081Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813013238/hb7081Isup3.cml

checkCIF report

Comment top

The title compound C₁₈H₂₅Br_NO₂S, was synthesized from 3,3-dibutyl-2,3- dihydro-8-methoxybenzo[b][1,4]thiazepin-4(5H)-one. The molecule is a bicyclic structure with one aromatic ring fused to a seven membered ring, on which two heteroatoms are present. The derivatives of this molecule able to provide high affinity ligands for more than one type of the receptor (Fedi et al., 2008). The compound is mainly used to treat schizophrenia and also find applications as neuroleptics, antidepressants, antihistaminic (Ganesh et al., 2011; Riedel et al., 2007). The N14—C13 bond is shorter than an usual N—C single bond [1.356 Å compared to 1.416 Å (Allen et al. 1987)]. The atoms C5, C6, C11 and C12 present in the central thiazepine ring forms a basal plane and the S10 atom as the bow, representing the boat conformation of thiazepine ring.

Related literature top

For reference bond lengths, see: Allen et al. (1987). For background to the uses of this class of compounds, see: Fedi et al. (2008); Ganesh et al. (2011); Riedel et al. (2007).

Experimental top

3,3-dibutyl-2,3-dihydro-8-methoxybenzo[b][1,4]thiazepin-4(5H)-one in dichloromethane, acetonitrile, cooled to 5°C and added N-bromosuccinimide over a period of 15 min. Then reaction mixture was brought to room temperature, stirred for 2 h and again cooled to 5°C, then N-bromosuccinimide is added at 5°C, cooled to -5°C for 1 h, filtered, washed with cold acetonitrile and then dried in vacuum and product was recrystallized from acetonitrile solution to yield light brown blocks.

Structure description top

For reference bond lengths, see: Allen et al. (1987). For background to the uses of this class of compounds, see: Fedi et al. (2008); Ganesh et al. (2011); Riedel et al. (2007).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. View of the title molecule with 50% probability ellipsoids.
	Fig. 2. Packing diagram of molecule, viewed along the crystallographic b axis.

7-Bromo-3,3-dibutyl-8-methoxy-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one top

Crystal data top

C₁₈H₂₆BrNO₂S	F(000) = 832
M_r = 400.30	D_x = 1.392 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4662 reflections
a = 7.7844 (18) Å	θ = 2.0–28.3°
b = 11.251 (2) Å	µ = 2.27 mm⁻¹
c = 22.039 (6) Å	T = 100 K
β = 98.199 (8)°	Block, light brown
V = 1910.5 (8) Å³	0.32 × 0.20 × 0.20 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2750 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 28.3°, θ_min = 2.0°
Detector resolution: 16.0839 pixels mm^-1	h = −10→8
ω scans	k = −14→9
16056 measured reflections	l = −29→29
4662 independent reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1275P)² + 0.4493P] where P = (F_o² + 2F_c²)/3
4662 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₈H₂₆BrNO₂S	V = 1910.5 (8) Å³
M_r = 400.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7844 (18) Å	µ = 2.27 mm⁻¹
b = 11.251 (2) Å	T = 100 K
c = 22.039 (6) Å	0.32 × 0.20 × 0.20 mm
β = 98.199 (8)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2750 reflections with I > 2σ(I)
16056 measured reflections	R_int = 0.054
4662 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.03	Δρ_max = 0.63 e Å⁻³
4662 reflections	Δρ_min = −0.49 e Å⁻³
212 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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
Br9	0.72841 (5)	0.01588 (4)	0.86915 (2)	0.0731 (2)
S10	0.09376 (11)	0.21269 (7)	0.99530 (4)	0.0494 (3)
O2	0.4327 (3)	−0.12202 (18)	0.90398 (11)	0.0548 (8)
O15	0.2816 (3)	0.53731 (17)	0.97428 (10)	0.0420 (7)
N14	0.3916 (3)	0.35886 (16)	0.95950 (10)	0.0418 (8)
C1	0.3047 (3)	−0.20519 (16)	0.91627 (10)	0.0621 (15)
C3	0.4122 (4)	−0.0060 (2)	0.91890 (15)	0.0399 (10)
C4	0.2747 (4)	0.0385 (3)	0.94491 (15)	0.0412 (10)
C5	0.2640 (4)	0.1590 (2)	0.95831 (14)	0.0383 (10)
C6	0.3919 (3)	0.2370 (2)	0.94450 (14)	0.0377 (9)
C7	0.5283 (4)	0.1922 (3)	0.91780 (15)	0.0424 (10)
C8	0.5387 (4)	0.0733 (3)	0.90492 (15)	0.0435 (10)
C11	−0.0156 (4)	0.3122 (3)	0.93772 (15)	0.0460 (10)
C12	0.0909 (4)	0.4072 (3)	0.90861 (14)	0.0386 (9)
C13	0.2596 (3)	0.4382 (2)	0.95076 (14)	0.0353 (9)
C16	−0.0182 (4)	0.5206 (3)	0.89941 (17)	0.0481 (11)
C17	−0.1953 (5)	0.5099 (3)	0.8591 (2)	0.0743 (16)
C18	−0.2889 (6)	0.6281 (5)	0.8496 (2)	0.0915 (19)
C19	−0.2269 (11)	0.7005 (6)	0.8047 (4)	0.165 (4)
C20	0.1333 (4)	0.3605 (3)	0.84640 (14)	0.0467 (11)
C21	0.2456 (6)	0.4427 (4)	0.81384 (18)	0.0743 (16)
C22	0.2854 (7)	0.3940 (6)	0.7533 (2)	0.105 (2)
C23	0.3966 (11)	0.4756 (7)	0.7214 (3)	0.165 (4)
H1A	0.30480	−0.21090	0.95970	0.0940*
H1B	0.33020	−0.28160	0.90040	0.0940*
H1C	0.19260	−0.17920	0.89700	0.0940*
H4	0.18770	−0.01270	0.95360	0.0490*
H7	0.61460	0.24340	0.90840	0.0510*
H11A	−0.07390	0.26350	0.90470	0.0550*
H11B	−0.10520	0.35340	0.95590	0.076 (12)*
H14	0.48930	0.38680	0.97670	0.061 (10)*
H16A	0.04900	0.58050	0.88150	0.0580*
H16B	−0.03720	0.54940	0.93940	0.053 (10)*
H17A	−0.17880	0.47760	0.81960	0.0890*
H17B	−0.26710	0.45470	0.87810	0.0890*
H18A	−0.41170	0.61340	0.83740	0.1100*
H18B	−0.27580	0.67080	0.88820	0.1100*
H19A	−0.12380	0.74130	0.82270	0.2470*
H19B	−0.31420	0.75760	0.78950	0.2470*
H19C	−0.20070	0.65160	0.77150	0.2470*
H20A	0.19210	0.28460	0.85320	0.0560*
H20B	0.02520	0.34660	0.81960	0.0560*
H21A	0.18690	0.51850	0.80660	0.0890*
H21B	0.35400	0.45680	0.84050	0.0890*
H22A	0.34410	0.31820	0.76050	0.1260*
H22B	0.17710	0.38000	0.72660	0.1260*
H23A	0.32730	0.54030	0.70310	0.2480*
H23B	0.44400	0.43230	0.69000	0.2480*
H23C	0.48940	0.50610	0.75050	0.2480*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br9	0.0585 (3)	0.0543 (3)	0.1145 (4)	0.0039 (2)	0.0399 (2)	−0.0172 (2)
S10	0.0463 (5)	0.0452 (5)	0.0608 (6)	−0.0023 (3)	0.0220 (4)	−0.0027 (4)
O2	0.0634 (15)	0.0289 (11)	0.0748 (16)	−0.0011 (10)	0.0188 (12)	−0.0065 (11)
O15	0.0329 (11)	0.0317 (11)	0.0600 (14)	−0.0040 (8)	0.0020 (10)	−0.0114 (10)
N14	0.0289 (13)	0.0310 (13)	0.0642 (17)	−0.0052 (10)	0.0019 (12)	−0.0106 (12)
C1	0.077 (3)	0.0328 (18)	0.076 (3)	−0.0101 (17)	0.009 (2)	−0.0023 (17)
C3	0.0439 (17)	0.0286 (15)	0.0460 (19)	−0.0026 (12)	0.0022 (14)	−0.0037 (13)
C4	0.0390 (16)	0.0333 (16)	0.052 (2)	−0.0074 (12)	0.0092 (14)	−0.0011 (14)
C5	0.0352 (16)	0.0348 (16)	0.0456 (18)	−0.0019 (12)	0.0082 (13)	−0.0042 (13)
C6	0.0296 (14)	0.0308 (15)	0.0513 (19)	−0.0023 (11)	0.0010 (13)	−0.0054 (13)
C7	0.0292 (15)	0.0367 (16)	0.062 (2)	−0.0051 (12)	0.0090 (14)	−0.0041 (15)
C8	0.0360 (16)	0.0391 (17)	0.057 (2)	0.0014 (13)	0.0125 (14)	−0.0067 (15)
C11	0.0302 (15)	0.0442 (17)	0.064 (2)	−0.0063 (13)	0.0080 (15)	−0.0109 (16)
C12	0.0308 (15)	0.0375 (16)	0.0469 (18)	−0.0047 (12)	0.0033 (13)	−0.0078 (14)
C13	0.0297 (14)	0.0309 (15)	0.0464 (18)	−0.0038 (11)	0.0097 (13)	−0.0034 (13)
C16	0.0361 (17)	0.0452 (18)	0.061 (2)	−0.0002 (13)	−0.0003 (16)	−0.0098 (16)
C17	0.050 (2)	0.064 (3)	0.099 (3)	0.0067 (18)	−0.023 (2)	−0.008 (2)
C18	0.072 (3)	0.098 (4)	0.093 (3)	0.040 (3)	−0.028 (3)	−0.029 (3)
C19	0.200 (8)	0.089 (4)	0.193 (8)	0.039 (5)	−0.013 (7)	0.019 (5)
C20	0.0398 (17)	0.0490 (19)	0.050 (2)	−0.0056 (14)	0.0020 (14)	−0.0106 (15)
C21	0.083 (3)	0.088 (3)	0.055 (2)	−0.022 (2)	0.021 (2)	−0.006 (2)
C22	0.108 (4)	0.159 (5)	0.052 (3)	−0.046 (4)	0.026 (3)	−0.017 (3)
C23	0.151 (7)	0.270 (10)	0.081 (4)	−0.078 (6)	0.037 (4)	−0.028 (5)

Geometric parameters (Å, º) top

Br9—C8	1.885 (3)	C1—H1A	0.9600
S10—C5	1.759 (3)	C1—H1B	0.9600
S10—C11	1.811 (3)	C1—H1C	0.9600
O2—C1	1.421 (3)	C4—H4	0.9300
O2—C3	1.361 (3)	C7—H7	0.9300
O15—C13	1.231 (3)	C11—H11A	0.9700
N14—C6	1.410 (3)	C11—H11B	0.9700
N14—C13	1.354 (3)	C16—H16A	0.9700
N14—H14	0.8600	C16—H16B	0.9700
C3—C4	1.378 (4)	C17—H17A	0.9700
C3—C8	1.395 (4)	C17—H17B	0.9700
C4—C5	1.393 (4)	C18—H18A	0.9700
C5—C6	1.393 (4)	C18—H18B	0.9700
C6—C7	1.381 (4)	C19—H19A	0.9600
C7—C8	1.372 (5)	C19—H19B	0.9600
C11—C12	1.547 (5)	C19—H19C	0.9600
C12—C13	1.537 (4)	C20—H20A	0.9700
C12—C16	1.530 (5)	C20—H20B	0.9700
C12—C20	1.547 (4)	C21—H21A	0.9700
C16—C17	1.535 (5)	C21—H21B	0.9700
C17—C18	1.517 (6)	C22—H22A	0.9700
C18—C19	1.418 (9)	C22—H22B	0.9700
C20—C21	1.521 (6)	C23—H23A	0.9600
C21—C22	1.515 (6)	C23—H23B	0.9600
C22—C23	1.503 (10)	C23—H23C	0.9600

C5—S10—C11	101.39 (14)	S10—C11—H11B	107.00
C1—O2—C3	118.4 (2)	C12—C11—H11A	107.00
C6—N14—C13	129.4 (2)	C12—C11—H11B	107.00
C13—N14—H14	115.00	H11A—C11—H11B	107.00
C6—N14—H14	115.00	C12—C16—H16A	108.00
C4—C3—C8	118.3 (3)	C12—C16—H16B	108.00
O2—C3—C4	125.0 (3)	C17—C16—H16A	108.00
O2—C3—C8	116.7 (3)	C17—C16—H16B	108.00
C3—C4—C5	121.0 (3)	H16A—C16—H16B	107.00
S10—C5—C4	120.3 (2)	C16—C17—H17A	109.00
S10—C5—C6	119.61 (18)	C16—C17—H17B	109.00
C4—C5—C6	120.1 (3)	C18—C17—H17A	109.00
N14—C6—C5	122.4 (2)	C18—C17—H17B	109.00
C5—C6—C7	118.7 (2)	H17A—C17—H17B	108.00
N14—C6—C7	118.8 (2)	C17—C18—H18A	109.00
C6—C7—C8	121.1 (3)	C17—C18—H18B	109.00
Br9—C8—C3	119.5 (2)	C19—C18—H18A	109.00
Br9—C8—C7	119.6 (2)	C19—C18—H18B	109.00
C3—C8—C7	120.9 (3)	H18A—C18—H18B	108.00
S10—C11—C12	119.4 (2)	C18—C19—H19A	110.00
C11—C12—C20	109.1 (3)	C18—C19—H19B	109.00
C13—C12—C16	107.5 (3)	C18—C19—H19C	109.00
C13—C12—C20	109.9 (2)	H19A—C19—H19B	109.00
C16—C12—C20	110.5 (3)	H19A—C19—H19C	109.00
C11—C12—C16	108.1 (3)	H19B—C19—H19C	110.00
C11—C12—C13	111.6 (2)	C12—C20—H20A	109.00
O15—C13—C12	121.0 (2)	C12—C20—H20B	109.00
O15—C13—N14	118.7 (2)	C21—C20—H20A	109.00
N14—C13—C12	120.1 (2)	C21—C20—H20B	109.00
C12—C16—C17	116.6 (3)	H20A—C20—H20B	108.00
C16—C17—C18	112.7 (3)	C20—C21—H21A	109.00
C17—C18—C19	113.3 (5)	C20—C21—H21B	109.00
C12—C20—C21	114.9 (3)	C22—C21—H21A	109.00
C20—C21—C22	113.5 (4)	C22—C21—H21B	109.00
C21—C22—C23	113.3 (5)	H21A—C21—H21B	108.00
O2—C1—H1A	109.00	C21—C22—H22A	109.00
O2—C1—H1B	109.00	C21—C22—H22B	109.00
O2—C1—H1C	109.00	C23—C22—H22A	109.00
H1A—C1—H1B	109.00	C23—C22—H22B	109.00
H1A—C1—H1C	109.00	H22A—C22—H22B	108.00
H1B—C1—H1C	110.00	C22—C23—H23A	109.00
C3—C4—H4	119.00	C22—C23—H23B	109.00
C5—C4—H4	119.00	C22—C23—H23C	110.00
C6—C7—H7	120.00	H23A—C23—H23B	109.00
C8—C7—H7	119.00	H23A—C23—H23C	110.00
S10—C11—H11A	107.00	H23B—C23—H23C	109.00

C11—S10—C5—C4	−117.4 (3)	C5—C6—C7—C8	0.0 (5)
C11—S10—C5—C6	65.0 (3)	C6—C7—C8—Br9	−179.4 (2)
C5—S10—C11—C12	−51.1 (3)	C6—C7—C8—C3	−0.5 (5)
C1—O2—C3—C4	−0.6 (5)	S10—C11—C12—C13	−23.9 (4)
C1—O2—C3—C8	−178.7 (3)	S10—C11—C12—C16	−142.0 (2)
C13—N14—C6—C5	−47.0 (4)	S10—C11—C12—C20	97.8 (3)
C13—N14—C6—C7	136.2 (3)	C11—C12—C13—O15	−113.0 (3)
C6—N14—C13—O15	170.9 (3)	C11—C12—C13—N14	71.2 (3)
C6—N14—C13—C12	−13.2 (4)	C16—C12—C13—O15	5.4 (4)
O2—C3—C4—C5	−179.6 (3)	C16—C12—C13—N14	−170.4 (3)
C8—C3—C4—C5	−1.5 (5)	C20—C12—C13—O15	125.7 (3)
O2—C3—C8—Br9	−1.6 (4)	C20—C12—C13—N14	−50.0 (4)
O2—C3—C8—C7	179.5 (3)	C11—C12—C16—C17	−58.6 (4)
C4—C3—C8—Br9	−179.9 (2)	C13—C12—C16—C17	−179.2 (3)
C4—C3—C8—C7	1.2 (5)	C20—C12—C16—C17	60.8 (4)
C3—C4—C5—S10	−176.5 (3)	C11—C12—C20—C21	−177.2 (3)
C3—C4—C5—C6	1.1 (5)	C13—C12—C20—C21	−54.5 (4)
S10—C5—C6—N14	0.5 (4)	C16—C12—C20—C21	64.1 (4)
S10—C5—C6—C7	177.3 (2)	C12—C16—C17—C18	−176.6 (3)
C4—C5—C6—N14	−177.2 (3)	C16—C17—C18—C19	79.1 (6)
C4—C5—C6—C7	−0.3 (5)	C12—C20—C21—C22	179.7 (3)
N14—C6—C7—C8	177.0 (3)	C20—C21—C22—C23	−179.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O15ⁱ	0.86	2.13	2.985 (3)	175
C11—H11B···O15ⁱⁱ	0.97	2.52	3.473 (4)	166

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₆BrNO₂S
M_r	400.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.7844 (18), 11.251 (2), 22.039 (6)
β (°)	98.199 (8)
V (Å³)	1910.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.32 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16056, 4662, 2750
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.141, 1.03
No. of reflections	4662
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.49

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Selected geometric parameters (Å, º) top

Br9—C8	1.885 (3)	O2—C3	1.361 (3)
S10—C5	1.759 (3)	O15—C13	1.231 (3)
S10—C11	1.811 (3)	N14—C6	1.410 (3)
O2—C1	1.421 (3)	N14—C13	1.354 (3)

C5—S10—C11	101.39 (14)	N14—C6—C7	118.8 (2)
C1—O2—C3	118.4 (2)	Br9—C8—C3	119.5 (2)
C6—N14—C13	129.4 (2)	Br9—C8—C7	119.6 (2)
O2—C3—C4	125.0 (3)	S10—C11—C12	119.4 (2)
O2—C3—C8	116.7 (3)	O15—C13—C12	121.0 (2)
S10—C5—C4	120.3 (2)	O15—C13—N14	118.7 (2)
S10—C5—C6	119.61 (18)	N14—C13—C12	120.1 (2)
N14—C6—C5	122.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O15ⁱ	0.8600	2.1300	2.985 (3)	175.00
C11—H11B···O15ⁱⁱ	0.9700	2.5200	3.473 (4)	166.00

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

Acknowledgements

MM thanks the IOE and the University of Mysore for the award of a fellowship and research grants. The data collection was performed at the Solid Sate and Structural Chemistry Unit, IISC.

References

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