(4-Bromo­phen­yl)(1-phenyl­sulfonyl-1H-indol-2-yl)methanone

Chakkaravarthi, G.; Panchatcharam, R.; Dhayalan, V.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S160053681004198X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2957

https://doi.org/10.1107/S160053681004198X

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(4-Bromophenyl)(1-phenylsulfonyl-1H-indol-2-yl)methanone

G. Chakkaravarthi,^a ^* R. Panchatcharam,^b V. Dhayalan,^c A. K. Mohanakrishnan ^c and V. Manivannan ^b

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 14 October 2010; accepted 16 October 2010; online 30 October 2010)

In the title compound, C₂₁H₁₄BrNO₃S, the indole ring system forms dihedral angles of 65.64 (8) and 59.30 (8)°, respectively, with the phenyl and bromophenyl rings. In the crystal, molecules are connected by a C—H⋯O hydrogen bond, forming a chain along [101]. The chains are further connected by weak intermolecular C—H⋯π interactions, forming a layer parallel to the ac plane.

Related literature

For the biological activity of indole derivatives, see: Joshi & Chand (1982 ); Pomarnacka & Kozlarska-Kedra (2003 ); Poter et al. (1977 ). For related structures, see: Chakkaravarthi et al. (2007 , 2008 ). For details of the configuration at the S atom, see: Bassindale (1984 ). For details of N-atom hybridization, see: Beddoes et al. (1986 ).

Experimental

Crystal data

C₂₁H₁₄BrNO₃S
M_r = 440.30
Monoclinic, P 2₁ /n
a = 8.482 (3) Å
b = 25.780 (4) Å
c = 8.690 (3) Å
β = 93.388 (3)°
V = 1896.9 (10) Å³
Z = 4
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 295 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.609, T_max = 0.656
18123 measured reflections
4736 independent reflections
2944 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.111
S = 1.03
4736 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C7/C8/C9/C14 and C9–C14 rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O3ⁱ	0.93	2.50	3.383 (3)	158
C4—H4⋯Cg1ⁱⁱ	0.93	2.67	3.635 (4)	127
C4—H4⋯Cg2ⁱⁱ	0.93	2.76	3.681 (4)	169
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, 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 I, global. DOI: https://doi.org/10.1107/S160053681004198X/is2617sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004198X/is2617Isup2.hkl

checkCIF report

Comment top

Indole derivatives are found abundantly in a variety of natural plants (Poter et al., 1977). Compounds containing the indole moiety exhibit antibacterial and fungicidal activities (Joshi & Chand, 1982). Indole derivatives are also known to exhibit anticancer and anti - HIV (Pomarnacka & Kozlarska-Kedra, 2003) activities.

In continuation of our studies of indole derivatives, we determined the crystal structure of the title compound,(I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported values for similar structures (Chakkaravarthi et al., 2007, 2008). Due to Thorpe–Ignold effect (Bassindale, 1984), bond angles around atom S1 show significant deviation from ideal tetrahedral value, with significant deviations in angles O2—S1—O1 [120.86 (13)°] and N1—S1—C1 [103.79 (11)°].

The phenyl ring forms the dihedral angle of 65.64 (8)° with the indole ring system and the bromophenyl ring makes the dihedral angle of 59.30 (8)° with the indole ring system. The N1—S1—C1 plane is almost orthogonal to both [dihedral angle 72.30 (9)°] indole ring and [dihedral angle 71.68 (12)°] phenyl ring.

The sum of the bond angles around N1 [341.7 (2)°] indicates that N1 atom is sp³ hybridized (Beddoes et al., 1986). The crystal packing is stabilized by weak intermolecular C—H···O and C—H···π [C4—H4···Cg1 (-1 + x, y, z) distance of 3.635 (4)Å and C4—H4···Cg2 (-1 + x, y, z) distance of 3.681 (4)Å (Cg1 and Cg2 are the centroids of the rings defined by the atoms N1/C7/C8/C9/C14 and C9—C14, respectively] interactions.

Related literature top

For the biological activity of indole derivatives, see: Joshi & Chand (1982); Pomarnacka & Kozlarska-Kedra (2003); Poter et al. (1977). For related structures, see: Chakkaravarthi et al. (2007, 2008). For details of the configuration at the S atom, see: Bassindale (1984). For details of N-atom hybridization, see: Beddoes et al. (1986).

Experimental top

To a solution of N-(2-Formylphenyl)benzenesulfonamide (0.5 g, 1.91 mmol) in dry CH₃CN (20 ml), K₂CO₃ (0.8 g, 5.79 mmol), 2-bromo-1-(4-bromophenyl)ethanone (0.63 g, 2.26 mmol) were added. The reaction mixture was stirred at room temperature for 6 h under N₂ atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml), extracted with chloroform (3 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by the residue was dissolved in CH₃CN (20 ml), Conc. HCl (3 ml) was added. The reaction mixture was then refluxed for 2 h. It was then poured over ice-water (50 ml), extracted with CHCl₃ (3 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by crystallization from methanol afforded the compound as a colourless crystal.

Structure description top

For the biological activity of indole derivatives, see: Joshi & Chand (1982); Pomarnacka & Kozlarska-Kedra (2003); Poter et al. (1977). For related structures, see: Chakkaravarthi et al. (2007, 2008). For details of the configuration at the S atom, see: Bassindale (1984). For details of N-atom hybridization, see: Beddoes et al. (1986).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (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 (I), with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. The packing of (I), viewed down the a axis. H-bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

(4-Bromophenyl)(1-phenylsulfonyl-1H-indol-2-yl)methanone top

Crystal data top

C₂₁H₁₄BrNO₃S	F(000) = 888
M_r = 440.30	D_x = 1.542 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4249 reflections
a = 8.482 (3) Å	θ = 2.5–24.4°
b = 25.780 (4) Å	µ = 2.30 mm⁻¹
c = 8.690 (3) Å	T = 295 K
β = 93.388 (3)°	Block, colourless
V = 1896.9 (10) Å³	0.24 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4736 independent reflections
Radiation source: fine-focus sealed tube	2944 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and φ scans	θ_max = 28.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.609, T_max = 0.656	k = −29→34
18123 measured reflections	l = −9→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0445P)² + 0.6759P] where P = (F_o² + 2F_c²)/3
4736 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₁H₁₄BrNO₃S	V = 1896.9 (10) Å³
M_r = 440.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.482 (3) Å	µ = 2.30 mm⁻¹
b = 25.780 (4) Å	T = 295 K
c = 8.690 (3) Å	0.24 × 0.22 × 0.20 mm
β = 93.388 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	4736 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2944 reflections with I > 2σ(I)
T_min = 0.609, T_max = 0.656	R_int = 0.035
18123 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.62 e Å⁻³
4736 reflections	Δρ_min = −0.46 e Å⁻³
244 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.24312 (5)	0.018422 (12)	0.53534 (5)	0.09126 (18)
S1	0.26404 (8)	0.34303 (3)	0.83609 (7)	0.04855 (18)
O1	0.3198 (2)	0.38893 (8)	0.9118 (2)	0.0648 (5)
O2	0.2576 (3)	0.29550 (8)	0.9169 (2)	0.0737 (6)
O3	0.5440 (2)	0.24395 (7)	0.8349 (2)	0.0671 (6)
N1	0.3837 (2)	0.33357 (7)	0.6910 (2)	0.0421 (5)
C1	0.0793 (3)	0.35548 (11)	0.7418 (3)	0.0494 (6)
C2	0.0204 (4)	0.40492 (12)	0.7428 (4)	0.0703 (9)
H2	0.0751	0.4312	0.7965	0.084*
C3	−0.1230 (4)	0.41519 (17)	0.6619 (5)	0.0963 (12)
H3	−0.1637	0.4487	0.6586	0.116*
C4	−0.2035 (4)	0.3756 (2)	0.5872 (5)	0.1035 (14)
H4	−0.3000	0.3824	0.5347	0.124*
C5	−0.1456 (4)	0.32696 (18)	0.5883 (4)	0.0901 (12)
H5	−0.2021	0.3006	0.5369	0.108*
C6	−0.0021 (4)	0.31602 (12)	0.6658 (3)	0.0650 (8)
H6	0.0386	0.2825	0.6665	0.078*
C7	0.4047 (3)	0.28357 (9)	0.6256 (3)	0.0410 (5)
C8	0.4166 (3)	0.28833 (10)	0.4728 (3)	0.0488 (6)
H8	0.4315	0.2612	0.4045	0.059*
C9	0.4027 (3)	0.34192 (10)	0.4327 (3)	0.0477 (6)
C10	0.4108 (4)	0.36829 (14)	0.2933 (4)	0.0706 (9)
H10	0.4263	0.3505	0.2024	0.085*
C11	0.3955 (4)	0.42089 (15)	0.2939 (4)	0.0827 (11)
H11	0.4003	0.4391	0.2019	0.099*
C12	0.3731 (4)	0.44741 (12)	0.4272 (5)	0.0769 (10)
H12	0.3629	0.4833	0.4230	0.092*
C13	0.3650 (3)	0.42278 (11)	0.5686 (4)	0.0613 (7)
H13	0.3494	0.4410	0.6587	0.074*
C14	0.3816 (3)	0.36928 (9)	0.5669 (3)	0.0438 (6)
C15	0.4561 (3)	0.23788 (10)	0.7209 (3)	0.0471 (6)
C16	0.4037 (3)	0.18560 (9)	0.6675 (3)	0.0430 (6)
C17	0.2741 (3)	0.17786 (10)	0.5660 (3)	0.0486 (6)
H17	0.2187	0.2062	0.5244	0.058*
C18	0.2266 (3)	0.12794 (11)	0.5260 (3)	0.0566 (7)
H18	0.1389	0.1226	0.4584	0.068*
C19	0.3100 (3)	0.08671 (10)	0.5870 (3)	0.0566 (7)
C20	0.4411 (4)	0.09344 (11)	0.6858 (4)	0.0656 (8)
H20	0.4980	0.0650	0.7246	0.079*
C21	0.4865 (3)	0.14285 (10)	0.7260 (3)	0.0586 (7)
H21	0.5744	0.1478	0.7936	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1039 (3)	0.04279 (18)	0.1244 (4)	−0.01215 (17)	−0.0165 (2)	−0.00695 (18)
S1	0.0576 (4)	0.0482 (4)	0.0396 (3)	0.0031 (3)	0.0004 (3)	−0.0035 (3)
O1	0.0676 (13)	0.0651 (12)	0.0596 (11)	0.0067 (10)	−0.0144 (10)	−0.0246 (10)
O2	0.0985 (17)	0.0670 (13)	0.0573 (12)	0.0100 (11)	0.0197 (11)	0.0186 (10)
O3	0.0788 (14)	0.0531 (11)	0.0650 (12)	0.0036 (10)	−0.0339 (11)	−0.0042 (9)
N1	0.0464 (12)	0.0357 (10)	0.0439 (11)	0.0020 (9)	−0.0010 (9)	0.0010 (8)
C1	0.0446 (15)	0.0566 (15)	0.0475 (14)	−0.0042 (12)	0.0073 (12)	−0.0093 (12)
C2	0.0522 (18)	0.066 (2)	0.092 (2)	0.0062 (15)	−0.0045 (16)	−0.0181 (17)
C3	0.059 (2)	0.103 (3)	0.125 (3)	0.022 (2)	−0.008 (2)	−0.009 (3)
C4	0.045 (2)	0.163 (5)	0.102 (3)	−0.002 (3)	−0.0044 (19)	−0.031 (3)
C5	0.054 (2)	0.129 (4)	0.088 (3)	−0.031 (2)	0.0063 (18)	−0.041 (2)
C6	0.0609 (19)	0.0685 (19)	0.0671 (19)	−0.0180 (15)	0.0171 (16)	−0.0198 (15)
C7	0.0391 (13)	0.0378 (12)	0.0452 (14)	0.0000 (10)	−0.0038 (10)	−0.0029 (10)
C8	0.0482 (15)	0.0539 (15)	0.0439 (15)	−0.0019 (12)	−0.0018 (12)	−0.0090 (12)
C9	0.0382 (14)	0.0604 (16)	0.0438 (14)	−0.0065 (12)	−0.0029 (11)	0.0067 (12)
C10	0.071 (2)	0.086 (2)	0.0539 (18)	−0.0102 (17)	−0.0008 (15)	0.0200 (16)
C11	0.079 (2)	0.095 (3)	0.073 (2)	−0.014 (2)	−0.0080 (18)	0.041 (2)
C12	0.067 (2)	0.0518 (17)	0.110 (3)	−0.0056 (15)	−0.0073 (19)	0.0329 (19)
C13	0.0565 (18)	0.0475 (15)	0.079 (2)	−0.0009 (13)	−0.0005 (15)	0.0073 (14)
C14	0.0349 (13)	0.0428 (13)	0.0533 (15)	−0.0032 (10)	−0.0025 (11)	0.0084 (11)
C15	0.0449 (14)	0.0445 (13)	0.0508 (15)	0.0057 (11)	−0.0058 (12)	−0.0023 (11)
C16	0.0421 (14)	0.0387 (12)	0.0475 (14)	0.0047 (10)	−0.0035 (11)	0.0000 (10)
C17	0.0422 (14)	0.0431 (13)	0.0590 (16)	0.0047 (11)	−0.0100 (12)	−0.0004 (11)
C18	0.0470 (16)	0.0503 (16)	0.0707 (18)	−0.0045 (12)	−0.0114 (14)	−0.0017 (13)
C19	0.0585 (17)	0.0387 (13)	0.0719 (19)	−0.0029 (12)	−0.0005 (14)	−0.0020 (12)
C20	0.071 (2)	0.0425 (15)	0.080 (2)	0.0129 (14)	−0.0178 (16)	0.0013 (14)
C21	0.0556 (17)	0.0489 (15)	0.0685 (18)	0.0082 (13)	−0.0212 (14)	0.0000 (13)

Geometric parameters (Å, º) top

Br1—C19	1.895 (3)	C8—H8	0.9300
S1—O2	1.415 (2)	C9—C14	1.384 (4)
S1—O1	1.4211 (19)	C9—C10	1.394 (4)
S1—N1	1.682 (2)	C10—C11	1.362 (5)
S1—C1	1.754 (3)	C10—H10	0.9300
O3—C15	1.215 (3)	C11—C12	1.368 (5)
N1—C14	1.417 (3)	C11—H11	0.9300
N1—C7	1.424 (3)	C12—C13	1.388 (4)
C1—C2	1.369 (4)	C12—H12	0.9300
C1—C6	1.376 (4)	C13—C14	1.386 (3)
C2—C3	1.394 (5)	C13—H13	0.9300
C2—H2	0.9300	C15—C16	1.485 (3)
C3—C4	1.370 (5)	C16—C17	1.382 (3)
C3—H3	0.9300	C16—C21	1.387 (3)
C4—C5	1.346 (6)	C17—C18	1.387 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.385 (5)	C18—C19	1.367 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.375 (4)
C7—C8	1.343 (3)	C20—C21	1.370 (4)
C7—C15	1.490 (3)	C20—H20	0.9300
C8—C9	1.428 (4)	C21—H21	0.9300

O2—S1—O1	120.86 (13)	C11—C10—C9	118.2 (3)
O2—S1—N1	106.80 (11)	C11—C10—H10	120.9
O1—S1—N1	105.58 (12)	C9—C10—H10	120.9
O2—S1—C1	109.31 (14)	C10—C11—C12	121.2 (3)
O1—S1—C1	109.10 (12)	C10—C11—H11	119.4
N1—S1—C1	103.79 (11)	C12—C11—H11	119.4
C14—N1—C7	106.31 (19)	C11—C12—C13	122.5 (3)
C14—N1—S1	119.67 (16)	C11—C12—H12	118.7
C7—N1—S1	121.71 (16)	C13—C12—H12	118.7
C2—C1—C6	121.2 (3)	C14—C13—C12	115.8 (3)
C2—C1—S1	118.9 (2)	C14—C13—H13	122.1
C6—C1—S1	119.9 (2)	C12—C13—H13	122.1
C1—C2—C3	118.8 (3)	C9—C14—C13	122.3 (2)
C1—C2—H2	120.6	C9—C14—N1	108.3 (2)
C3—C2—H2	120.6	C13—C14—N1	129.4 (2)
C4—C3—C2	119.6 (4)	O3—C15—C16	122.0 (2)
C4—C3—H3	120.2	O3—C15—C7	119.8 (2)
C2—C3—H3	120.2	C16—C15—C7	118.1 (2)
C5—C4—C3	121.3 (4)	C17—C16—C21	119.0 (2)
C5—C4—H4	119.4	C17—C16—C15	122.8 (2)
C3—C4—H4	119.4	C21—C16—C15	118.1 (2)
C4—C5—C6	120.2 (3)	C16—C17—C18	120.2 (2)
C4—C5—H5	119.9	C16—C17—H17	119.9
C6—C5—H5	119.9	C18—C17—H17	119.9
C1—C6—C5	119.0 (3)	C19—C18—C17	119.2 (2)
C1—C6—H6	120.5	C19—C18—H18	120.4
C5—C6—H6	120.5	C17—C18—H18	120.4
C8—C7—N1	109.3 (2)	C18—C19—C20	121.7 (3)
C8—C7—C15	125.8 (2)	C18—C19—Br1	119.3 (2)
N1—C7—C15	122.2 (2)	C20—C19—Br1	119.0 (2)
C7—C8—C9	108.6 (2)	C21—C20—C19	118.8 (3)
C7—C8—H8	125.7	C21—C20—H20	120.6
C9—C8—H8	125.7	C19—C20—H20	120.6
C14—C9—C10	120.0 (3)	C20—C21—C16	121.1 (2)
C14—C9—C8	107.5 (2)	C20—C21—H21	119.4
C10—C9—C8	132.5 (3)	C16—C21—H21	119.4

O2—S1—N1—C14	163.63 (18)	C10—C11—C12—C13	0.1 (5)
O1—S1—N1—C14	−66.5 (2)	C11—C12—C13—C14	0.2 (5)
C1—S1—N1—C14	48.2 (2)	C10—C9—C14—C13	1.2 (4)
O2—S1—N1—C7	26.6 (2)	C8—C9—C14—C13	179.6 (2)
O1—S1—N1—C7	156.43 (18)	C10—C9—C14—N1	−177.8 (2)
C1—S1—N1—C7	−88.8 (2)	C8—C9—C14—N1	0.6 (3)
O2—S1—C1—C2	138.5 (2)	C12—C13—C14—C9	−0.9 (4)
O1—S1—C1—C2	4.3 (3)	C12—C13—C14—N1	177.9 (3)
N1—S1—C1—C2	−107.9 (2)	C7—N1—C14—C9	−0.8 (3)
O2—S1—C1—C6	−42.9 (3)	S1—N1—C14—C9	−143.64 (18)
O1—S1—C1—C6	−177.1 (2)	C7—N1—C14—C13	−179.7 (2)
N1—S1—C1—C6	70.7 (2)	S1—N1—C14—C13	37.5 (3)
C6—C1—C2—C3	−1.5 (5)	C8—C7—C15—O3	127.2 (3)
S1—C1—C2—C3	177.1 (3)	N1—C7—C15—O3	−32.1 (4)
C1—C2—C3—C4	1.8 (6)	C8—C7—C15—C16	−49.7 (4)
C2—C3—C4—C5	−1.1 (7)	N1—C7—C15—C16	151.0 (2)
C3—C4—C5—C6	0.0 (6)	O3—C15—C16—C17	162.2 (3)
C2—C1—C6—C5	0.5 (4)	C7—C15—C16—C17	−20.9 (4)
S1—C1—C6—C5	−178.1 (2)	O3—C15—C16—C21	−16.0 (4)
C4—C5—C6—C1	0.3 (5)	C7—C15—C16—C21	160.8 (2)
C14—N1—C7—C8	0.7 (3)	C21—C16—C17—C18	1.2 (4)
S1—N1—C7—C8	142.63 (19)	C15—C16—C17—C18	−177.0 (2)
C14—N1—C7—C15	163.0 (2)	C16—C17—C18—C19	−0.5 (4)
S1—N1—C7—C15	−55.1 (3)	C17—C18—C19—C20	−0.8 (5)
N1—C7—C8—C9	−0.4 (3)	C17—C18—C19—Br1	178.9 (2)
C15—C7—C8—C9	−161.9 (2)	C18—C19—C20—C21	1.4 (5)
C7—C8—C9—C14	−0.1 (3)	Br1—C19—C20—C21	−178.3 (2)
C7—C8—C9—C10	178.0 (3)	C19—C20—C21—C16	−0.7 (5)
C14—C9—C10—C11	−0.8 (4)	C17—C16—C21—C20	−0.6 (4)
C8—C9—C10—C11	−178.7 (3)	C15—C16—C21—C20	177.7 (3)
C9—C10—C11—C12	0.2 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/C7/C8/C9/C14 and C9—C14 rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O3ⁱ	0.93	2.50	3.383 (3)	158
C4—H4···Cg1ⁱⁱ	0.93	2.67	3.635 (4)	127
C4—H4···Cg2ⁱⁱ	0.93	2.76	3.681 (4)	169

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄BrNO₃S
M_r	440.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	8.482 (3), 25.780 (4), 8.690 (3)
β (°)	93.388 (3)
V (Å³)	1896.9 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.609, 0.656
No. of measured, independent and observed [I > 2σ(I)] reflections	18123, 4736, 2944
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.111, 1.03
No. of reflections	4736
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.46

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/C7/C8/C9/C14 and C9—C14 rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O3ⁱ	0.93	2.50	3.383 (3)	158
C4—H4···Cg1ⁱⁱ	0.93	2.67	3.635 (4)	127
C4—H4···Cg2ⁱⁱ	0.93	2.76	3.681 (4)	169

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

Acknowledgements

The authors wish to acknowledge DV University of Madras for the data collection.

References

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