{2-[(1,3-Benzo­thia­zol-2-yl)meth­oxy]-5-bromo­phen­yl}(phen­yl)methanone

Venugopala, K.N.; Nayak, S.K.; Odhav, B.

doi:10.1107/S1600536813014086

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o984

doi:10.1107/S1600536813014086

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{2-[(1,3-Benzothiazol-2-yl)methoxy]-5-bromophenyl}(phenyl)methanone

K. N. Venugopala,^a ^* Susanta K. Nayak ^b ^* and B. Odhav ^a

^aDepartment of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa, and ^bEquipe Chimie du Solide et Matériaux, UMR 6226 Institut des Sciences, Université de Rennes 1, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes Cedex, France
^*Correspondence e-mail: katharigattav@dut.ac.za, nksusa@gmail.com

(Received 12 May 2013; accepted 21 May 2013; online 31 May 2013)

In the title compound, C₂₁H₁₄BrNO₂S, the dihedral angle between the planes of the benzothiazole and phenylmethanone groups is 63.4 (2)°. In the crystal, pairs of C—H⋯N hydrogen bonds link the molecules to form inversion dimers, which are further linked by C—H⋯O interactions into chains along the c axis. C—H⋯π and π–π interactions [centroid–centroid distance = 3.863 (1) Å] further stabilize the molecular assembly.

Related literature

For background to the applications of benzothiazole derivatives, see: Kelarev et al. (2003 ); Rana et al. (2007 ); Telvekar et al. (2012 ); Saeed et al. (2010 ).

Experimental

Crystal data

C₂₁H₁₄BrNO₂S
M_r = 424.30
Monoclinic, P 2₁ /n
a = 15.1475 (6) Å
b = 7.6501 (3) Å
c = 15.8339 (6) Å
β = 102.105 (3)°
V = 1794.03 (12) Å³
Z = 4
Mo Kα radiation
μ = 2.42 mm⁻¹
T = 292 K
0.23 × 0.21 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.606, T_max = 0.670
19116 measured reflections
3525 independent reflections
1971 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.120
S = 0.98
3525 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C1/C6/N1/C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯N1ⁱ	0.93	2.55	3.398 (6)	152
C5—H5⋯O2ⁱⁱ	0.93	2.61	3.505 (6)	161
C20—H20⋯Cg1ⁱⁱⁱ	0.93	2.68	3.459 (4)	142
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y+1, z.

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: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813014086/ff2107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813014086/ff2107Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813014086/ff2107Isup3.cml

checkCIF report

Comment top

Substituted benzothiazole derivatives have been reported to exhibit various pharmacological properties such as analgesic, antibacterial, antifungal, antidepressant, antitumor, antihypertensive, anthelmintic, and herbicidal activity (Kelarev et al., 2003). However, the variety of biological features of new benzothiazole derivatives is of great scientific interest (Telvekar et al., 2012; Saeed et al., 2010). Here, we report the single-crystal structure of the title compound.

The title compound prefers the conformation with the dihedral angle 63.4 (2)° between the planes of benzothiazole and phenylmethanone group (Fig. 1). The weak C—H···N hydrogen bonds lead to dimer formation, whereas C—H···O hydrogen bonds connect the molecules into infinite chains (Fig. 2a), which leads to formation of layers parallel to (-101). Further, the C—H···π interactions involving the five membered ring S1/C1/C6/N1/C7 and π–π [Cg2···Cg3 = 3.863 (1) Å, Cg2 is the centroid of the six membered ring C9—C14 and Cg3 is the centroid of the six membered ring C16—C21] stabilize the criss-cross molecular assembly (Fig 2 b).

Related literature top

For background to the applications of benzothiazole derivatives, see: Kelarev et al. (2003); Rana et al. (2007); Telvekar et al. (2012); Saeed et al. (2010).

Experimental top

To a mixture of (2-chloromethyl)benzo[d]thiazole (1 mmol) and (5-bromo-2-hydroxyphenyl)(phenyl)methanone (1 mmol) in dry THF, dry potassium carbonate (1 mmol) was added and the reaction mixture was stirred at room temperature for 14 h. The reaction mixture was concentrated to remove the solvent, diluted with ethyl acetate, washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated to yield a residue which was purified by column chromatography using ethyl acetate and n-hexane as eluent (7:3, Rf = 0.71) to afford the product in 77% as a white solid (m. p. 407 (2) K). Suitable crystals for single-crystal X-ray study were obtained from acetonitrile solvent using slow evaporation technique at room temperature.

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: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. Molecular structure shows the atom labelling scheme with displacement ellipsoids for non-H atoms at 30% probability level, hydrogen atoms are arbitrary circles.
	Fig. 2. (a) The dimer formation (C—H···N bonds) and their interaction by C—H···O hydrogen bonds. (b) additional C—H···π and π–π interactions stabilize the criss-cross molecular assembly; view along the c axis.

{2-[(1,3-Benzothiazol-2-yl)methoxy]-5-bromophenyl}(phenyl)methanone top

Crystal data top

C₂₁H₁₄BrNO₂S	F(000) = 856
M_r = 424.30	D_x = 1.571 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 407(2) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.7107 Å
a = 15.1475 (6) Å	Cell parameters from 350 reflections
b = 7.6501 (3) Å	θ = 1.0–28.0°
c = 15.8339 (6) Å	µ = 2.42 mm⁻¹
β = 102.105 (3)°	T = 292 K
V = 1794.03 (12) Å³	Block, colourless
Z = 4	0.23 × 0.21 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer	3525 independent reflections
Radiation source: Mova (Mo) X-ray Source	1971 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.088
Detector resolution: 16.0839 pixels mm^-1	θ_max = 26.0°, θ_min = 2.6°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
T_min = 0.606, T_max = 0.670	l = −19→19
19116 measured 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0408P)²] where P = (F_o² + 2F_c²)/3
3525 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₁H₁₄BrNO₂S	V = 1794.03 (12) Å³
M_r = 424.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.1475 (6) Å	µ = 2.42 mm⁻¹
b = 7.6501 (3) Å	T = 292 K
c = 15.8339 (6) Å	0.23 × 0.21 × 0.18 mm
β = 102.105 (3)°

Data collection top

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer	3525 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1971 reflections with I > 2σ(I)
T_min = 0.606, T_max = 0.670	R_int = 0.088
19116 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 0.98	Δρ_max = 0.34 e Å⁻³
3525 reflections	Δρ_min = −0.32 e Å⁻³
235 parameters

Special details top

Experimental. CrysAlisPro (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Br1	0.47887 (4)	0.70720 (7)	0.07925 (3)	0.0671 (2)
S1	−0.04002 (8)	0.33280 (15)	0.17148 (7)	0.0513 (3)
O1	0.1169 (2)	0.4165 (4)	0.11024 (17)	0.0499 (8)
N1	−0.0810 (2)	0.1671 (4)	0.0260 (2)	0.0410 (9)
O2	0.2746 (2)	0.5691 (4)	0.31997 (18)	0.0587 (9)
C6	−0.1521 (3)	0.1423 (5)	0.0671 (3)	0.0389 (10)
C15	0.2206 (3)	0.5983 (5)	0.2529 (3)	0.0395 (10)
C8	0.0664 (3)	0.3039 (5)	0.0468 (3)	0.0424 (11)
H8A	0.1004	0.1981	0.0423	0.051*
H8B	0.0539	0.3614	−0.0090	0.051*
C16	0.1297 (3)	0.6683 (5)	0.2544 (2)	0.0351 (10)
C21	0.0809 (3)	0.7618 (5)	0.1858 (3)	0.0396 (11)
H21	0.1031	0.7750	0.1357	0.048*
C9	0.1982 (3)	0.4790 (5)	0.0998 (3)	0.0397 (10)
C7	−0.0190 (3)	0.2608 (5)	0.0734 (2)	0.0379 (10)
C14	0.2497 (3)	0.5708 (5)	0.1688 (2)	0.0368 (10)
C12	0.3650 (3)	0.6114 (5)	0.0873 (3)	0.0443 (11)
C4	−0.2920 (3)	0.0222 (6)	0.0832 (4)	0.0662 (14)
H4	−0.3432	−0.0445	0.0621	0.079*
C5	−0.2287 (3)	0.0427 (6)	0.0339 (3)	0.0535 (12)
H5	−0.2364	−0.0086	−0.0204	0.064*
C18	0.0136 (3)	0.7221 (6)	0.3328 (3)	0.0554 (13)
H18	−0.0090	0.7088	0.3827	0.066*
C2	−0.2067 (3)	0.1994 (6)	0.1977 (3)	0.0600 (14)
H2	−0.1998	0.2520	0.2517	0.072*
C20	−0.0003 (3)	0.8356 (5)	0.1912 (3)	0.0507 (12)
H20	−0.0325	0.8996	0.1449	0.061*
C1	−0.1411 (3)	0.2200 (5)	0.1478 (3)	0.0438 (11)
C19	−0.0345 (3)	0.8158 (6)	0.2644 (3)	0.0560 (13)
H19	−0.0898	0.8653	0.2676	0.067*
C11	0.3151 (3)	0.5212 (6)	0.0191 (3)	0.0494 (12)
H11	0.3365	0.5058	−0.0313	0.059*
C17	0.0947 (3)	0.6485 (6)	0.3280 (3)	0.0472 (12)
H17	0.1266	0.5846	0.3745	0.057*
C10	0.2324 (3)	0.4533 (5)	0.0261 (3)	0.0470 (12)
H10	0.1990	0.3892	−0.0195	0.056*
C13	0.3333 (3)	0.6361 (5)	0.1623 (3)	0.0436 (11)
H13	0.3682	0.6967	0.2084	0.052*
C3	−0.2813 (4)	0.0995 (7)	0.1649 (4)	0.0688 (15)
H3	−0.3252	0.0830	0.1972	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0546 (4)	0.0762 (4)	0.0768 (4)	−0.0116 (3)	0.0282 (3)	−0.0030 (3)
S1	0.0522 (8)	0.0533 (8)	0.0482 (7)	−0.0063 (6)	0.0098 (6)	−0.0133 (6)
O1	0.045 (2)	0.055 (2)	0.0503 (19)	−0.0147 (16)	0.0117 (15)	−0.0175 (15)
N1	0.038 (2)	0.043 (2)	0.038 (2)	0.0021 (18)	0.0004 (18)	0.0006 (17)
O2	0.050 (2)	0.079 (2)	0.0432 (19)	0.0160 (18)	0.0014 (16)	−0.0005 (17)
C6	0.036 (3)	0.034 (2)	0.042 (3)	0.005 (2)	−0.001 (2)	0.000 (2)
C15	0.041 (3)	0.034 (2)	0.040 (3)	−0.006 (2)	0.001 (2)	0.001 (2)
C8	0.045 (3)	0.040 (3)	0.042 (3)	−0.003 (2)	0.007 (2)	−0.006 (2)
C16	0.033 (3)	0.034 (2)	0.036 (2)	−0.004 (2)	0.002 (2)	−0.0054 (19)
C21	0.044 (3)	0.030 (2)	0.044 (3)	−0.001 (2)	0.006 (2)	0.004 (2)
C9	0.035 (3)	0.039 (3)	0.045 (3)	0.002 (2)	0.009 (2)	−0.003 (2)
C7	0.037 (3)	0.037 (2)	0.038 (3)	0.007 (2)	0.004 (2)	0.004 (2)
C14	0.036 (3)	0.040 (3)	0.034 (2)	0.003 (2)	0.0060 (19)	−0.001 (2)
C12	0.042 (3)	0.038 (3)	0.055 (3)	0.005 (2)	0.014 (2)	0.002 (2)
C4	0.040 (3)	0.059 (3)	0.097 (4)	−0.002 (3)	0.010 (3)	0.008 (3)
C5	0.038 (3)	0.052 (3)	0.065 (3)	−0.003 (2)	−0.001 (2)	−0.004 (2)
C18	0.047 (3)	0.081 (4)	0.043 (3)	−0.002 (3)	0.019 (2)	−0.006 (3)
C2	0.058 (4)	0.062 (3)	0.064 (3)	0.006 (3)	0.020 (3)	−0.003 (3)
C20	0.053 (3)	0.036 (3)	0.059 (3)	0.005 (2)	0.002 (3)	0.001 (2)
C1	0.044 (3)	0.037 (3)	0.048 (3)	0.004 (2)	0.004 (2)	0.006 (2)
C19	0.039 (3)	0.057 (3)	0.072 (4)	0.000 (3)	0.011 (3)	−0.011 (3)
C11	0.053 (3)	0.053 (3)	0.044 (3)	0.006 (3)	0.016 (2)	−0.003 (2)
C17	0.051 (3)	0.053 (3)	0.037 (3)	0.001 (2)	0.007 (2)	0.003 (2)
C10	0.049 (3)	0.043 (3)	0.046 (3)	−0.003 (2)	0.006 (2)	−0.012 (2)
C13	0.041 (3)	0.041 (3)	0.047 (3)	−0.002 (2)	0.005 (2)	−0.002 (2)
C3	0.059 (4)	0.062 (4)	0.094 (4)	0.005 (3)	0.034 (3)	0.005 (3)

Geometric parameters (Å, º) top

Br1—C12	1.903 (4)	C12—C11	1.368 (6)
S1—C1	1.729 (5)	C12—C13	1.383 (5)
S1—C7	1.739 (4)	C4—C5	1.366 (6)
O1—C9	1.363 (4)	C4—C3	1.399 (6)
O1—C8	1.418 (4)	C4—H4	0.9300
N1—C7	1.289 (5)	C5—H5	0.9300
N1—C6	1.382 (5)	C18—C17	1.367 (6)
O2—C15	1.218 (4)	C18—C19	1.374 (6)
C6—C1	1.388 (6)	C18—H18	0.9300
C6—C5	1.395 (5)	C2—C3	1.373 (6)
C15—C16	1.482 (5)	C2—C1	1.401 (6)
C15—C14	1.502 (5)	C2—H2	0.9300
C8—C7	1.480 (5)	C20—C19	1.372 (6)
C8—H8A	0.9700	C20—H20	0.9300
C8—H8B	0.9700	C19—H19	0.9300
C16—C21	1.379 (5)	C11—C10	1.382 (5)
C16—C17	1.387 (5)	C11—H11	0.9300
C21—C20	1.373 (6)	C17—H17	0.9300
C21—H21	0.9300	C10—H10	0.9300
C9—C10	1.385 (5)	C13—H13	0.9300
C9—C14	1.393 (5)	C3—H3	0.9300
C14—C13	1.386 (5)

C1—S1—C7	88.2 (2)	C3—C4—H4	119.3
C9—O1—C8	119.5 (3)	C4—C5—C6	118.4 (5)
C7—N1—C6	110.3 (3)	C4—C5—H5	120.8
N1—C6—C1	114.8 (4)	C6—C5—H5	120.8
N1—C6—C5	124.5 (4)	C17—C18—C19	120.3 (4)
C1—C6—C5	120.6 (4)	C17—C18—H18	119.8
O2—C15—C16	120.6 (4)	C19—C18—H18	119.8
O2—C15—C14	118.6 (4)	C3—C2—C1	118.2 (5)
C16—C15—C14	120.8 (4)	C3—C2—H2	120.9
O1—C8—C7	107.9 (3)	C1—C2—H2	120.9
O1—C8—H8A	110.1	C19—C20—C21	120.6 (4)
C7—C8—H8A	110.1	C19—C20—H20	119.7
O1—C8—H8B	110.1	C21—C20—H20	119.7
C7—C8—H8B	110.1	C6—C1—C2	120.6 (4)
H8A—C8—H8B	108.4	C6—C1—S1	110.0 (3)
C21—C16—C17	118.8 (4)	C2—C1—S1	129.4 (4)
C21—C16—C15	121.4 (4)	C20—C19—C18	119.5 (5)
C17—C16—C15	119.7 (4)	C20—C19—H19	120.3
C20—C21—C16	120.3 (4)	C18—C19—H19	120.3
C20—C21—H21	119.9	C12—C11—C10	119.1 (4)
C16—C21—H21	119.9	C12—C11—H11	120.5
O1—C9—C10	124.0 (4)	C10—C11—H11	120.5
O1—C9—C14	116.9 (4)	C18—C17—C16	120.5 (4)
C10—C9—C14	119.0 (4)	C18—C17—H17	119.7
N1—C7—C8	122.1 (4)	C16—C17—H17	119.7
N1—C7—S1	116.6 (3)	C11—C10—C9	121.3 (4)
C8—C7—S1	121.2 (3)	C11—C10—H10	119.3
C13—C14—C9	119.6 (4)	C9—C10—H10	119.3
C13—C14—C15	117.3 (4)	C12—C13—C14	120.1 (4)
C9—C14—C15	123.1 (4)	C12—C13—H13	119.9
C11—C12—C13	120.8 (4)	C14—C13—H13	119.9
C11—C12—Br1	120.0 (3)	C2—C3—C4	120.8 (5)
C13—C12—Br1	119.2 (3)	C2—C3—H3	119.6
C5—C4—C3	121.3 (5)	C4—C3—H3	119.6
C5—C4—H4	119.3

C7—N1—C6—C1	−0.4 (5)	C1—C6—C5—C4	−0.6 (6)
C7—N1—C6—C5	−178.1 (4)	C16—C21—C20—C19	−0.7 (6)
C9—O1—C8—C7	−178.5 (3)	N1—C6—C1—C2	−177.6 (4)
O2—C15—C16—C21	155.4 (4)	C5—C6—C1—C2	0.2 (6)
C14—C15—C16—C21	−21.3 (6)	N1—C6—C1—S1	1.8 (4)
O2—C15—C16—C17	−20.9 (6)	C5—C6—C1—S1	179.5 (3)
C14—C15—C16—C17	162.4 (4)	C3—C2—C1—C6	0.5 (7)
C17—C16—C21—C20	0.9 (6)	C3—C2—C1—S1	−178.7 (4)
C15—C16—C21—C20	−175.5 (4)	C7—S1—C1—C6	−1.9 (3)
C8—O1—C9—C10	6.4 (6)	C7—S1—C1—C2	177.4 (4)
C8—O1—C9—C14	−172.2 (4)	C21—C20—C19—C18	0.5 (7)
C6—N1—C7—C8	178.2 (4)	C17—C18—C19—C20	−0.4 (7)
C6—N1—C7—S1	−1.2 (4)	C13—C12—C11—C10	−0.5 (6)
O1—C8—C7—N1	176.5 (4)	Br1—C12—C11—C10	−179.7 (3)
O1—C8—C7—S1	−4.2 (5)	C19—C18—C17—C16	0.5 (7)
C1—S1—C7—N1	1.8 (3)	C21—C16—C17—C18	−0.7 (6)
C1—S1—C7—C8	−177.5 (3)	C15—C16—C17—C18	175.7 (4)
O1—C9—C14—C13	179.4 (4)	C12—C11—C10—C9	1.8 (6)
C10—C9—C14—C13	0.7 (6)	O1—C9—C10—C11	179.5 (4)
O1—C9—C14—C15	1.6 (6)	C14—C9—C10—C11	−1.9 (6)
C10—C9—C14—C15	−177.1 (4)	C11—C12—C13—C14	−0.6 (6)
O2—C15—C14—C13	−45.6 (5)	Br1—C12—C13—C14	178.6 (3)
C16—C15—C14—C13	131.2 (4)	C9—C14—C13—C12	0.5 (6)
O2—C15—C14—C9	132.2 (4)	C15—C14—C13—C12	178.4 (4)
C16—C15—C14—C9	−50.9 (6)	C1—C2—C3—C4	−0.7 (7)
C3—C4—C5—C6	0.4 (7)	C5—C4—C3—C2	0.3 (8)
N1—C6—C5—C4	176.9 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the S1/C1/C6/N1/C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···N1ⁱ	0.93	2.55	3.398 (6)	152
C5—H5···O2ⁱⁱ	0.93	2.61	3.505 (6)	161
C20—H20···Cg1ⁱⁱⁱ	0.93	2.68	3.459 (4)	142

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄BrNO₂S
M_r	424.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	15.1475 (6), 7.6501 (3), 15.8339 (6)
β (°)	102.105 (3)
V (Å³)	1794.03 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.42
Crystal size (mm)	0.23 × 0.21 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Eos, Nova) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.606, 0.670
No. of measured, independent and observed [I > 2σ(I)] reflections	19116, 3525, 1971
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.120, 0.98
No. of reflections	3525
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.32

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the S1/C1/C6/N1/C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···N1ⁱ	0.93	2.55	3.398 (6)	152
C5—H5···O2ⁱⁱ	0.93	2.61	3.505 (6)	161
C20—H20···Cg1ⁱⁱⁱ	0.93	2.68	3.459 (4)	142

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

Acknowledgements

We are thankful to SSCU, IISc, India for the Oxford Diffraction facility funded under DST–FIST (Level II) and Durban University of Technology for facilities. KNV thanks the NRF South Africa for a DST/NRF Innovation Postdoctoral Fellowship.

References

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