N-(5-Bromo-2-chloro­benz­yl)-N-cyclo­propyl­naphthalene-2-sulfonamide

Babu, C.S.M.; Kavitha, H.P.; Arulmozhi, R.; Vennila, J.P.; Manivannan, V.

doi:10.1107/S1600536809014457

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1098

doi:10.1107/S1600536809014457

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N-(5-Bromo-2-chlorobenzyl)-N-cyclopropylnaphthalene-2-sulfonamide

C. Suneel Manohar Babu,^a Helen P. Kavitha,^b R. Arulmozhi,^c Jasmine P. Vennila ^d and V. Manivannan ^e ^*

^aNicholas Piramal Research Centre, Nicholas Piramal India Limited, Mumbai 400 063, India, ^bDepartment of Chemistry, SRM University, Ramapuram, Chennai 600 089, India, ^cDepartment of Chemistry, SRM University, Kattankulathur Campus, Kanchipuram, India, ^dDepartment of Physics, Panimalar Institute of Technology, Chennai 600 095, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 13 April 2009; accepted 17 April 2009; online 22 April 2009)

In the title compound, C₂₀H₁₇BrClNO₂S, the dihedral angle between the benzene ring and the naphthalene plane is 8.95 (8)°. The crystal packing is stabilized by weak intermolecular C—H⋯O, C—H⋯Cl and π–π [centroid–centroid distance = 3.8782 (16) Å] interactions.

Related literature

For biological activity, see: Li et al. (1995 ); Maren (1976 ); Misra et al. (1982 ); Yoshino et al. (1992 ). For related structures, see: Ramachandran et al. (2008 ); Vennila et al. (2009 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₇BrClNO₂S
M_r = 450.77
Monoclinic, P 2₁ /c
a = 12.1759 (5) Å
b = 7.5881 (3) Å
c = 20.5752 (8) Å
β = 95.393 (1)°
V = 1892.57 (13) Å³
Z = 4
Mo Kα radiation
μ = 2.44 mm⁻¹
T = 295 K
0.22 × 0.18 × 0.14 mm

Data collection

Bruker KappaAPEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.616, T_max = 0.727
23845 measured reflections
5240 independent reflections
3528 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.103
S = 1.01
5240 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.81 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cl1ⁱ	0.98	2.79	3.612 (3)	142
C12—H12⋯O2ⁱⁱ	0.93	2.36	3.231 (3)	156
Symmetry codes: (i) -x-1, -y+1, -z; (ii) -x-1, -y+2, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014457/gk2206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014457/gk2206Isup2.hkl

checkCIF report

Comment top

Sulfonamides exhibit antibacterial (Misra et al., 1982), insulin-releasing (Maren, 1976), anti-inflammatory (Li et al., 1995) and antitumor (Yoshino et al., 1992) activities. The geometric parameters in the title compound agree with the reported values of similar structure (Ramachandran et al., 2008; Vennila et al., 2009).

The dihedral angle between the phenyl ring and naphthalene ring is 8.95 (8)°. The geometry around S1 atom is distorted from a regular tetrahedron [O1—S1—N1 = 107.09 (10) °; O2—S1—N1 = 105.66 (11)°; O1—S1—C11 = 108.25 (10)°]. The molecular structure is stabilized by weak intramolecular C—H···O and C—H···N interactions and the crystal packing is stabilized by a weak intermolecular C—H···O, C—H···Cl (Fig. 2) and π–π [Cg2···Cg4(-1 - x, 1 - y, -z) = 3.8782 (16) Å; Cg2-centroid of ring C1–C6; Cg4-centroid of C13–C18 ring] interactions.

The intermolecular C8—H8···Cl1 interaction generates 14-membered ring, with graph-set motif R₂²(14) and C16—H16···O2 interaction generates ten-membered ring, with graph-set motif R₂²(10).

Related literature top

For biological activity, see: Li et al. (1995); Maren (1976); Misra et al. (1982); Yoshino et al. (1992). For similar molecules, see: Ramachandran et al. (2008); Vennila et al. (2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

1 g (3.6 mmol) of 5-bromo-2-chloro-benzyl-cyclopropyl-amine is dissolved in 20 ml of ethyl acetate. To the above mixture, 0.57 g (7.2 mmol) of pyridine is added with stirring and then 0.7 g (3 mmol) of naphthalene-2-sulfonyl chloride is added and heated to 50 °C for 6 h. The reaction mass is cooled to room temperature and 20 ml of water is added. The aqueous layer is separated. The ethyl acetate layer is washed twice with 10% sodium chloride solution and dried over 2 g of anhydrous sodium sulfate. The solvent is removed under vacuum and the crude product obtained is recrystallized from hexane–ethyl acetate mixture to get diffraction quality white crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, viewed down the a axis. H-bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

N-(5-Bromo-2-chlorobenzyl)-N-cyclopropylnaphthalene-2-sulfonamide top

Crystal data top

C₂₀H₁₇BrClNO₂S	F(000) = 912
M_r = 450.77	D_x = 1.582 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6275 reflections
a = 12.1759 (5) Å	θ = 2.5–29.7°
b = 7.5881 (3) Å	µ = 2.44 mm⁻¹
c = 20.5752 (8) Å	T = 295 K
β = 95.393 (1)°	Block, colourless
V = 1892.57 (13) Å³	0.22 × 0.18 × 0.14 mm
Z = 4

Data collection top

Bruker KappaAPEXII diffractometer	5240 independent reflections
Radiation source: fine-focus sealed tube	3528 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scans	θ_max = 29.7°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.616, T_max = 0.727	k = −9→10
23845 measured reflections	l = −28→26

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0433P)² + 1.1018P] where P = (F_o² + 2F_c²)/3
5240 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

C₂₀H₁₇BrClNO₂S	V = 1892.57 (13) Å³
M_r = 450.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1759 (5) Å	µ = 2.44 mm⁻¹
b = 7.5881 (3) Å	T = 295 K
c = 20.5752 (8) Å	0.22 × 0.18 × 0.14 mm
β = 95.393 (1)°

Data collection top

Bruker KappaAPEXII diffractometer	5240 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3528 reflections with I > 2σ(I)
T_min = 0.616, T_max = 0.727	R_int = 0.029
23845 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.01	Δρ_max = 0.71 e Å⁻³
5240 reflections	Δρ_min = −0.81 e Å⁻³
235 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.04003 (2)	0.91779 (4)	0.097687 (17)	0.06646 (13)
Cl1	−0.44538 (6)	0.63579 (10)	0.11975 (3)	0.05481 (18)
S1	−0.36612 (5)	0.92504 (8)	−0.10261 (2)	0.03567 (13)
N1	−0.31258 (15)	0.7424 (3)	−0.07080 (8)	0.0388 (4)
O1	−0.30118 (14)	0.9756 (3)	−0.15345 (8)	0.0490 (4)
O2	−0.37562 (15)	1.0407 (3)	−0.04900 (8)	0.0528 (5)
C1	−0.27720 (18)	0.7338 (3)	0.05050 (10)	0.0360 (5)
C2	−0.17142 (18)	0.7960 (3)	0.04688 (11)	0.0411 (5)
H2	−0.1449	0.8125	0.0064	0.049*
C3	−0.1051 (2)	0.8337 (4)	0.10303 (13)	0.0465 (6)
C4	−0.1415 (2)	0.8122 (4)	0.16319 (13)	0.0607 (8)
H4	−0.0957	0.8388	0.2006	0.073*
C5	−0.2464 (2)	0.7508 (4)	0.16785 (12)	0.0583 (7)
H5	−0.2722	0.7350	0.2086	0.070*
C6	−0.31283 (19)	0.7129 (3)	0.11212 (11)	0.0405 (5)
C7	−0.3536 (2)	0.6863 (4)	−0.00886 (11)	0.0484 (6)
H7A	−0.3642	0.5596	−0.0098	0.058*
H7B	−0.4249	0.7406	−0.0052	0.058*
C8	−0.2972 (2)	0.6020 (3)	−0.11672 (13)	0.0488 (6)
H8	−0.3642	0.5537	−0.1402	0.059*
C9	−0.1969 (3)	0.6016 (5)	−0.15207 (18)	0.0736 (10)
H9A	−0.2033	0.5561	−0.1963	0.088*
H9B	−0.1454	0.6984	−0.1441	0.088*
C10	−0.2075 (3)	0.4754 (5)	−0.0985 (2)	0.0897 (12)
H10A	−0.1625	0.4949	−0.0577	0.108*
H10B	−0.2203	0.3526	−0.1099	0.108*
C11	−0.49910 (18)	0.8701 (3)	−0.13796 (10)	0.0345 (5)
C20	−0.5150 (2)	0.8332 (4)	−0.20527 (10)	0.0441 (6)
H20	−0.4573	0.8467	−0.2314	0.053*
C19	−0.6153 (2)	0.7776 (4)	−0.23142 (11)	0.0472 (6)
H19	−0.6263	0.7558	−0.2760	0.057*
C18	−0.70337 (19)	0.7521 (3)	−0.19266 (11)	0.0421 (5)
C13	−0.68651 (18)	0.7903 (3)	−0.12488 (11)	0.0365 (5)
C12	−0.58277 (18)	0.8532 (3)	−0.09876 (10)	0.0352 (5)
H12	−0.5714	0.8832	−0.0548	0.042*
C17	−0.8073 (2)	0.6872 (4)	−0.21798 (14)	0.0573 (7)
H17	−0.8205	0.6641	−0.2624	0.069*
C16	−0.8879 (2)	0.6582 (4)	−0.17825 (16)	0.0655 (8)
H16	−0.9558	0.6147	−0.1957	0.079*
C15	−0.8704 (2)	0.6928 (4)	−0.11131 (15)	0.0590 (7)
H15	−0.9263	0.6700	−0.0846	0.071*
C14	−0.7729 (2)	0.7593 (4)	−0.08508 (13)	0.0476 (6)
H14	−0.7628	0.7846	−0.0407	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03377 (15)	0.0702 (2)	0.0924 (2)	−0.00308 (13)	−0.00958 (14)	0.00913 (17)
Cl1	0.0471 (4)	0.0642 (4)	0.0555 (3)	−0.0071 (3)	0.0171 (3)	0.0071 (3)
S1	0.0333 (3)	0.0404 (3)	0.0328 (2)	−0.0043 (2)	0.0008 (2)	0.0009 (2)
N1	0.0352 (10)	0.0467 (12)	0.0339 (8)	−0.0017 (9)	0.0002 (7)	0.0075 (8)
O1	0.0417 (9)	0.0582 (12)	0.0474 (9)	−0.0087 (8)	0.0056 (7)	0.0160 (8)
O2	0.0506 (11)	0.0555 (12)	0.0511 (9)	−0.0067 (9)	−0.0021 (8)	−0.0184 (8)
C1	0.0338 (11)	0.0356 (13)	0.0379 (10)	0.0029 (9)	0.0001 (8)	0.0086 (9)
C2	0.0325 (11)	0.0468 (15)	0.0434 (11)	0.0000 (10)	0.0009 (9)	0.0110 (10)
C3	0.0341 (12)	0.0456 (15)	0.0578 (14)	0.0034 (11)	−0.0066 (10)	0.0072 (12)
C4	0.0596 (17)	0.074 (2)	0.0452 (13)	−0.0058 (15)	−0.0117 (12)	0.0014 (14)
C5	0.0649 (18)	0.073 (2)	0.0376 (12)	−0.0087 (16)	0.0059 (12)	0.0004 (13)
C6	0.0394 (12)	0.0396 (14)	0.0432 (11)	0.0007 (10)	0.0065 (9)	0.0068 (10)
C7	0.0396 (13)	0.0652 (18)	0.0394 (11)	−0.0108 (12)	−0.0004 (10)	0.0158 (12)
C8	0.0416 (14)	0.0456 (16)	0.0587 (14)	0.0003 (11)	0.0016 (11)	0.0001 (12)
C9	0.0554 (19)	0.076 (2)	0.093 (2)	0.0054 (16)	0.0246 (17)	−0.0170 (19)
C10	0.090 (3)	0.073 (3)	0.103 (3)	0.033 (2)	−0.004 (2)	−0.003 (2)
C11	0.0329 (11)	0.0381 (13)	0.0317 (9)	0.0020 (9)	−0.0007 (8)	−0.0017 (9)
C20	0.0456 (13)	0.0547 (16)	0.0322 (10)	−0.0004 (12)	0.0045 (9)	−0.0022 (10)
C19	0.0485 (14)	0.0599 (17)	0.0317 (10)	0.0022 (12)	−0.0042 (10)	−0.0084 (11)
C18	0.0380 (12)	0.0424 (14)	0.0439 (12)	0.0037 (10)	−0.0070 (10)	−0.0073 (10)
C13	0.0316 (11)	0.0343 (13)	0.0432 (11)	0.0044 (9)	0.0018 (9)	−0.0033 (10)
C12	0.0339 (11)	0.0393 (13)	0.0320 (9)	0.0051 (10)	0.0008 (8)	−0.0054 (9)
C17	0.0422 (14)	0.0650 (19)	0.0612 (15)	0.0001 (13)	−0.0141 (12)	−0.0118 (14)
C16	0.0355 (14)	0.070 (2)	0.087 (2)	−0.0029 (14)	−0.0123 (14)	−0.0122 (17)
C15	0.0324 (13)	0.063 (2)	0.082 (2)	0.0015 (13)	0.0083 (13)	0.0011 (15)
C14	0.0373 (13)	0.0525 (16)	0.0534 (13)	0.0046 (12)	0.0059 (10)	−0.0023 (12)

Geometric parameters (Å, º) top

Br1—C3	1.891 (3)	C9—C10	1.475 (5)
Cl1—C6	1.738 (2)	C9—H9A	0.9700
S1—O1	1.4220 (16)	C9—H9B	0.9700
S1—O2	1.4229 (17)	C10—H10A	0.9700
S1—N1	1.641 (2)	C10—H10B	0.9700
S1—C11	1.761 (2)	C11—C12	1.363 (3)
N1—C8	1.448 (3)	C11—C20	1.409 (3)
N1—C7	1.475 (3)	C20—C19	1.356 (3)
C1—C2	1.380 (3)	C20—H20	0.9300
C1—C6	1.387 (3)	C19—C18	1.408 (3)
C1—C7	1.508 (3)	C19—H19	0.9300
C2—C3	1.376 (3)	C18—C17	1.411 (3)
C2—H2	0.9300	C18—C13	1.420 (3)
C3—C4	1.363 (4)	C13—C12	1.409 (3)
C4—C5	1.371 (4)	C13—C14	1.412 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.370 (4)	C17—C16	1.353 (4)
C5—H5	0.9300	C17—H17	0.9300
C7—H7A	0.9700	C16—C15	1.399 (4)
C7—H7B	0.9700	C16—H16	0.9300
C8—C10	1.475 (4)	C15—C14	1.355 (4)
C8—C9	1.478 (4)	C15—H15	0.9300
C8—H8	0.9800	C14—H14	0.9300

O1—S1—O2	119.67 (12)	C8—C9—H9A	117.8
O1—S1—N1	107.09 (10)	C10—C9—H9B	117.8
O2—S1—N1	105.66 (11)	C8—C9—H9B	117.8
O1—S1—C11	108.25 (10)	H9A—C9—H9B	114.9
O2—S1—C11	109.11 (11)	C9—C10—C8	60.1 (2)
N1—S1—C11	106.27 (11)	C9—C10—H10A	117.8
C8—N1—C7	115.3 (2)	C8—C10—H10A	117.8
C8—N1—S1	115.61 (15)	C9—C10—H10B	117.8
C7—N1—S1	115.72 (17)	C8—C10—H10B	117.8
C2—C1—C6	117.5 (2)	H10A—C10—H10B	114.9
C2—C1—C7	123.1 (2)	C12—C11—C20	121.5 (2)
C6—C1—C7	119.4 (2)	C12—C11—S1	119.14 (15)
C3—C2—C1	120.2 (2)	C20—C11—S1	119.26 (17)
C3—C2—H2	119.9	C19—C20—C11	119.2 (2)
C1—C2—H2	119.9	C19—C20—H20	120.4
C4—C3—C2	121.5 (2)	C11—C20—H20	120.4
C4—C3—Br1	118.6 (2)	C20—C19—C18	121.6 (2)
C2—C3—Br1	119.94 (19)	C20—C19—H19	119.2
C3—C4—C5	119.3 (2)	C18—C19—H19	119.2
C3—C4—H4	120.4	C19—C18—C17	122.9 (2)
C5—C4—H4	120.4	C19—C18—C13	118.7 (2)
C6—C5—C4	119.6 (2)	C17—C18—C13	118.4 (2)
C6—C5—H5	120.2	C12—C13—C14	121.7 (2)
C4—C5—H5	120.2	C12—C13—C18	119.0 (2)
C5—C6—C1	122.0 (2)	C14—C13—C18	119.3 (2)
C5—C6—Cl1	118.39 (19)	C11—C12—C13	119.95 (19)
C1—C6—Cl1	119.60 (18)	C11—C12—H12	120.0
N1—C7—C1	113.43 (19)	C13—C12—H12	120.0
N1—C7—H7A	108.9	C16—C17—C18	120.7 (3)
C1—C7—H7A	108.9	C16—C17—H17	119.7
N1—C7—H7B	108.9	C18—C17—H17	119.7
C1—C7—H7B	108.9	C17—C16—C15	120.9 (3)
H7A—C7—H7B	107.7	C17—C16—H16	119.6
N1—C8—C10	116.8 (3)	C15—C16—H16	119.6
N1—C8—C9	119.1 (2)	C14—C15—C16	120.6 (3)
C10—C8—C9	59.9 (2)	C14—C15—H15	119.7
N1—C8—H8	116.4	C16—C15—H15	119.7
C10—C8—H8	116.4	C15—C14—C13	120.2 (2)
C9—C8—H8	116.4	C15—C14—H14	119.9
C10—C9—C8	59.9 (2)	C13—C14—H14	119.9
C10—C9—H9A	117.8

O1—S1—N1—C8	−52.60 (19)	N1—C8—C10—C9	−109.7 (3)
O2—S1—N1—C8	178.78 (17)	O1—S1—C11—C12	−166.32 (19)
C11—S1—N1—C8	62.93 (19)	O2—S1—C11—C12	−34.6 (2)
O1—S1—N1—C7	168.24 (16)	N1—S1—C11—C12	78.9 (2)
O2—S1—N1—C7	39.62 (19)	O1—S1—C11—C20	17.9 (2)
C11—S1—N1—C7	−76.22 (18)	O2—S1—C11—C20	149.7 (2)
C6—C1—C2—C3	0.4 (4)	N1—S1—C11—C20	−96.8 (2)
C7—C1—C2—C3	−178.7 (2)	C12—C11—C20—C19	−0.8 (4)
C1—C2—C3—C4	−0.4 (4)	S1—C11—C20—C19	174.9 (2)
C1—C2—C3—Br1	179.70 (19)	C11—C20—C19—C18	−1.5 (4)
C2—C3—C4—C5	0.3 (5)	C20—C19—C18—C17	−177.2 (3)
Br1—C3—C4—C5	−179.8 (2)	C20—C19—C18—C13	1.6 (4)
C3—C4—C5—C6	−0.3 (5)	C19—C18—C13—C12	0.4 (4)
C4—C5—C6—C1	0.3 (5)	C17—C18—C13—C12	179.3 (2)
C4—C5—C6—Cl1	−179.9 (2)	C19—C18—C13—C14	−177.7 (2)
C2—C1—C6—C5	−0.4 (4)	C17—C18—C13—C14	1.1 (4)
C7—C1—C6—C5	178.8 (3)	C20—C11—C12—C13	2.8 (4)
C2—C1—C6—Cl1	179.79 (19)	S1—C11—C12—C13	−172.87 (18)
C7—C1—C6—Cl1	−1.0 (3)	C14—C13—C12—C11	175.5 (2)
C8—N1—C7—C1	120.9 (2)	C18—C13—C12—C11	−2.6 (3)
S1—N1—C7—C1	−99.8 (2)	C19—C18—C17—C16	177.3 (3)
C2—C1—C7—N1	−10.4 (4)	C13—C18—C17—C16	−1.5 (4)
C6—C1—C7—N1	170.4 (2)	C18—C17—C16—C15	0.4 (5)
C7—N1—C8—C10	−68.4 (3)	C17—C16—C15—C14	1.2 (5)
S1—N1—C8—C10	152.3 (2)	C16—C15—C14—C13	−1.6 (4)
C7—N1—C8—C9	−137.2 (3)	C12—C13—C14—C15	−177.7 (3)
S1—N1—C8—C9	83.5 (3)	C18—C13—C14—C15	0.4 (4)
N1—C8—C9—C10	105.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1	0.93	2.52	2.864 (3)	102
C20—H20···O1	0.93	2.56	2.926 (3)	104
C8—H8···Cl1ⁱ	0.98	2.79	3.612 (3)	142
C12—H12···O2ⁱⁱ	0.93	2.36	3.231 (3)	156

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇BrClNO₂S
M_r	450.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.1759 (5), 7.5881 (3), 20.5752 (8)
β (°)	95.393 (1)
V (Å³)	1892.57 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.44
Crystal size (mm)	0.22 × 0.18 × 0.14

Data collection
Diffractometer	Bruker KappaAPEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.616, 0.727
No. of measured, independent and observed [I > 2σ(I)] reflections	23845, 5240, 3528
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.697

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.103, 1.01
No. of reflections	5240
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.81

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1	0.93	2.52	2.864 (3)	102
C20—H20···O1	0.93	2.56	2.926 (3)	104
C8—H8···Cl1ⁱ	0.98	2.79	3.612 (3)	142
C12—H12···O2ⁱⁱ	0.93	2.36	3.231 (3)	156

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

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

References

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