Crystal structure of N-{[3-bromo-1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}benzene­sulfonamide

Umadevi, M.; Raju, P.; Yamuna, R.; Mohanakrishnan, A.K.; Chakkaravarthi, G.

doi:10.1107/S2056989015016874

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o756-o757

doi:10.1107/S2056989015016874

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Crystal structure of N-{[3-bromo-1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide

M. Umadevi,^a,^b P. Raju,^c R. Yamuna,^d ^* A. K. Mohanakrishnan ^c and G. Chakkaravarthi ^e ^*

^aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, India, ^bDepartment of Chemistry, Pallavan College of Engineering, Kanchipuram 631 502, India, ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^dDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and ^eDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 7 September 2015; accepted 9 September 2015; online 17 September 2015)

In the title compound, C₂₁H₁₇BrN₂O₄S₂, the indole ring system subtends dihedral angles of 85.96 (13) and 9.62 (16)° with the planes of the N- and C-bonded benzene rings, respectively. The dihedral angles between the benzene rings is 88.05 (17)°. The molecular conformation is stabilized by intramolecular N—H⋯O and C—H⋯O hydrogen bonds and an aromatic π–π stacking [centroid-to-centroid distance = 3.503 (2) Å] interaction. In the crystal, short Br⋯O [2.9888 (18) Å] contacts link the molecules into [010] chains. The chains are cross-linked by weak C—H⋯π interactions, forming a three-dimensional network.

Keywords: crystal structure; benzenesulfonamide; phenylsulfonyl; biological activity; derivatives; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1423139

1. Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ); Andreev et al. (2015 ); Kolocouris et al. (1994 ). For related structures, see: Chakkaravarthi et al. (2007 , 2008 ).

2. Experimental

2.1. Crystal data

C₂₁H₁₇BrN₂O₄S₂
M_r = 505.40
Monoclinic, P 2₁ /c
a = 7.5129 (6) Å
b = 17.4245 (14) Å
c = 16.0988 (14) Å
β = 98.087 (3)°
V = 2086.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.20 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.22 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.578, T_max = 0.643
23680 measured reflections
3808 independent reflections
2942 reflections with I > 2σ(I)
R_int = 0.042

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.02
3808 reflections
275 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.87 (1)	2.17 (3)	2.795 (3)	128 (3)
C13—H13⋯O2	0.93	2.38	2.954 (4)	120
C21—H21⋯Cg2ⁱ	0.93	2.81	3.667 (3)	155
Symmetry code: (i) 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 and PLATON.

Supporting information

CCDC reference: 1423139

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015016874/hb7501sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016874/hb7501Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015016874/hb7501Isup3.cml

checkCIF report

Comment top

Indole derivatives are known to exhibit activities such as antitumour (Andreani et al., 2001); anti-hepatitis C virus (Andreev et al., 2015) and antiviral (Kolocouris et al., 1994). We herein report the crystal structure of (I). The ORTEP diagram of the title compound (I) is shown in Fig. 1. The geometric parameters of (I) are comparable with the reported similar structures (Chakkaravarthi et al. 2007, 2008). The phenyl rings (C1—C6) and (C16—C21) form the dihedral angles of 85.96 (13)° and 9.62 (16)°, respectively with the indole ring system. The phenyl rings (C1—C6) and (C16—C21) are orthogonal to each other, with the dihedral angle of 88.05 (17)°.

The molecular structure (Fig. 1) is stabilized by weak intramolecular N—H···O, C—H···O and C—H···Br hydrogen bonds (Table 1) and π–π [centroid-to-centroid distance = 3.503 (2) Å] interaction. In the crystal structure, the intermolecular weak Br···O [Br1···O2ⁱ and O2··· Br1ⁱⁱ contacts at 2.99 Å; (i) (1 - x,-1/2 + y,1/2 - z); (ii) 1 - x,1/2 + y,1/2 - z)] contacts form the molecules into infinite one-dimensional chain along [0 1 0] and these chains are further influenced by weak C—H···π interactions (Table 1) to form a three dimensional network.

Related literature top

For the biological activity of indole derivatives, see: Andreani et al. (2001); Andreev et al. (2015); Kolocouris et al. (1994). For related structures, see: Chakkaravarthi et al. (2007, 2008).

Experimental top

To a solution of 3-bromo-2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole (0.5 g, 1.16 mmol) in acetonitrile (10 ml) was added K₂CO₃ (0.32 g, 2.33 mmol) and benzenesulphonamide (0.23 g, 1.51 mmol). The reaction mixture was then stirred at reflux for 12 h. After completion of the reaction (monitored by TLC), it was cooled to room temperature and reaction mass was poured over crushed ice (30 g). The solid obtained was filtered and dried. The crude product was recrystallized from methanol to afford the title compound as colourless blocks.

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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

N-{[3-Bromo-1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide top

Crystal data top

C₂₁H₁₇BrN₂O₄S₂	F(000) = 1024
M_r = 505.40	D_x = 1.609 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7461 reflections
a = 7.5129 (6) Å	θ = 2.3–24.4°
b = 17.4245 (14) Å	µ = 2.20 mm⁻¹
c = 16.0988 (14) Å	T = 295 K
β = 98.087 (3)°	Block, colourless
V = 2086.5 (3) Å³	0.28 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3808 independent reflections
Radiation source: fine-focus sealed tube	2942 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω and φ scan	θ_max = 25.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.578, T_max = 0.643	k = −20→20
23680 measured reflections	l = −19→19

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) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.055P)² + 0.8751P] where P = (F_o² + 2F_c²)/3
3808 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.60 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₁H₁₇BrN₂O₄S₂	V = 2086.5 (3) Å³
M_r = 505.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5129 (6) Å	µ = 2.20 mm⁻¹
b = 17.4245 (14) Å	T = 295 K
c = 16.0988 (14) Å	0.28 × 0.24 × 0.22 mm
β = 98.087 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3808 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2942 reflections with I > 2σ(I)
T_min = 0.578, T_max = 0.643	R_int = 0.042
23680 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.60 e Å⁻³
3808 reflections	Δρ_min = −0.40 e Å⁻³
275 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
C1	0.2432 (4)	0.19281 (14)	0.09825 (16)	0.0381 (6)
C2	0.1728 (4)	0.25496 (16)	0.13721 (19)	0.0481 (7)
H2	0.2437	0.2827	0.1788	0.058*
C3	−0.0038 (4)	0.27433 (19)	0.1127 (2)	0.0594 (8)
H3	−0.0543	0.3151	0.1384	0.071*
C4	−0.1065 (4)	0.2335 (2)	0.0501 (2)	0.0611 (9)
H4	−0.2255	0.2476	0.0332	0.073*
C5	−0.0355 (4)	0.1724 (2)	0.0126 (2)	0.0601 (8)
H5	−0.1065	0.1450	−0.0293	0.072*
C6	0.1410 (4)	0.15136 (17)	0.03663 (18)	0.0498 (7)
H6	0.1900	0.1098	0.0115	0.060*
C7	0.4610 (4)	0.02955 (14)	0.20280 (17)	0.0396 (6)
C8	0.4202 (4)	0.00661 (15)	0.27698 (19)	0.0460 (7)
C9	0.4154 (4)	0.07015 (17)	0.33242 (18)	0.0453 (7)
C10	0.3906 (5)	0.0770 (2)	0.4160 (2)	0.0625 (9)
H10	0.3682	0.0340	0.4471	0.075*
C11	0.4000 (5)	0.1484 (3)	0.4513 (2)	0.0736 (11)
H11	0.3829	0.1540	0.5071	0.088*
C12	0.4344 (5)	0.2125 (2)	0.4059 (2)	0.0692 (10)
H12	0.4376	0.2605	0.4314	0.083*
C13	0.4638 (4)	0.20715 (18)	0.32402 (18)	0.0544 (8)
H13	0.4891	0.2503	0.2938	0.065*
C14	0.4545 (4)	0.13474 (16)	0.28803 (16)	0.0408 (6)
C15	0.5031 (4)	−0.01861 (16)	0.13068 (18)	0.0494 (7)
H15A	0.4799	−0.0719	0.1430	0.059*
H15B	0.4206	−0.0045	0.0812	0.059*
N2	0.6852 (4)	−0.01280 (14)	0.11069 (15)	0.0499 (6)
C16	0.8919 (4)	0.02153 (17)	0.26010 (18)	0.0480 (7)
C17	0.8597 (5)	−0.0015 (2)	0.3376 (2)	0.0676 (9)
H17	0.8240	−0.0515	0.3468	0.081*
C18	0.8818 (6)	0.0519 (4)	0.4024 (2)	0.0907 (15)
H18	0.8611	0.0378	0.4559	0.109*
C19	0.9337 (6)	0.1249 (3)	0.3874 (3)	0.0932 (15)
H19	0.9473	0.1604	0.4310	0.112*
C20	0.9656 (6)	0.1467 (2)	0.3107 (3)	0.0802 (11)
H20	1.0023	0.1966	0.3017	0.096*
C21	0.9440 (5)	0.09537 (18)	0.2461 (2)	0.0615 (9)
H21	0.9645	0.1103	0.1928	0.074*
N1	0.4842 (3)	0.11047 (11)	0.20700 (13)	0.0390 (5)
O1	0.5276 (3)	0.12773 (11)	0.05899 (11)	0.0453 (5)
O2	0.5650 (3)	0.23686 (10)	0.15614 (13)	0.0495 (5)
O3	1.0073 (3)	−0.03343 (15)	0.12907 (15)	0.0726 (7)
O4	0.8142 (4)	−0.11538 (13)	0.20432 (18)	0.0801 (8)
S1	0.47029 (9)	0.16993 (3)	0.12591 (4)	0.03756 (17)
S2	0.85938 (11)	−0.04228 (4)	0.17424 (5)	0.0547 (2)
Br1	0.39126 (5)	−0.095232 (19)	0.30887 (3)	0.07287 (16)
H2A	0.709 (4)	0.0315 (11)	0.0891 (19)	0.063 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0491 (15)	0.0309 (13)	0.0358 (14)	0.0022 (11)	0.0105 (12)	0.0067 (11)
C2	0.0550 (18)	0.0405 (15)	0.0503 (17)	0.0039 (13)	0.0131 (14)	−0.0015 (13)
C3	0.060 (2)	0.0540 (19)	0.068 (2)	0.0136 (15)	0.0194 (17)	0.0043 (16)
C4	0.0473 (18)	0.074 (2)	0.063 (2)	0.0076 (16)	0.0136 (16)	0.0215 (18)
C5	0.057 (2)	0.070 (2)	0.0511 (19)	−0.0028 (16)	−0.0004 (15)	0.0005 (16)
C6	0.0585 (18)	0.0481 (16)	0.0429 (16)	0.0051 (14)	0.0071 (14)	−0.0033 (13)
C7	0.0458 (15)	0.0278 (13)	0.0426 (16)	0.0014 (11)	−0.0027 (12)	−0.0019 (11)
C8	0.0471 (16)	0.0343 (14)	0.0553 (18)	0.0013 (12)	0.0029 (13)	0.0114 (13)
C9	0.0449 (16)	0.0508 (16)	0.0395 (16)	0.0082 (13)	0.0032 (12)	0.0066 (13)
C10	0.060 (2)	0.083 (2)	0.0459 (19)	0.0155 (18)	0.0124 (15)	0.0165 (17)
C11	0.082 (3)	0.103 (3)	0.0357 (18)	0.020 (2)	0.0081 (17)	−0.011 (2)
C12	0.084 (2)	0.075 (2)	0.047 (2)	0.0125 (19)	0.0021 (17)	−0.0225 (18)
C13	0.071 (2)	0.0479 (17)	0.0427 (17)	0.0051 (15)	0.0013 (14)	−0.0102 (14)
C14	0.0477 (15)	0.0429 (15)	0.0305 (14)	0.0059 (12)	0.0016 (12)	−0.0033 (12)
C15	0.066 (2)	0.0318 (14)	0.0467 (17)	−0.0015 (13)	−0.0036 (14)	−0.0077 (12)
N2	0.0670 (17)	0.0384 (13)	0.0434 (14)	0.0101 (12)	0.0046 (12)	−0.0085 (11)
C16	0.0510 (17)	0.0538 (17)	0.0376 (16)	0.0071 (14)	0.0004 (13)	−0.0008 (13)
C17	0.064 (2)	0.087 (3)	0.050 (2)	0.0044 (19)	0.0009 (16)	0.0105 (19)
C18	0.070 (3)	0.165 (5)	0.036 (2)	0.011 (3)	0.0040 (17)	−0.011 (3)
C19	0.069 (3)	0.130 (4)	0.076 (3)	0.009 (3)	−0.004 (2)	−0.053 (3)
C20	0.082 (3)	0.079 (3)	0.077 (3)	−0.003 (2)	−0.002 (2)	−0.030 (2)
C21	0.073 (2)	0.057 (2)	0.054 (2)	0.0000 (16)	0.0075 (17)	−0.0085 (16)
N1	0.0539 (14)	0.0284 (11)	0.0333 (12)	0.0019 (9)	0.0017 (10)	−0.0019 (9)
O1	0.0563 (12)	0.0433 (10)	0.0378 (11)	0.0081 (9)	0.0116 (9)	0.0007 (8)
O2	0.0572 (12)	0.0313 (9)	0.0611 (13)	−0.0067 (8)	0.0115 (10)	−0.0007 (9)
O3	0.0705 (15)	0.0824 (17)	0.0664 (15)	0.0217 (13)	0.0144 (12)	−0.0178 (13)
O4	0.103 (2)	0.0382 (12)	0.0928 (19)	0.0131 (12)	−0.0088 (15)	0.0084 (12)
S1	0.0483 (4)	0.0282 (3)	0.0369 (4)	0.0012 (3)	0.0085 (3)	0.0019 (3)
S2	0.0689 (5)	0.0416 (4)	0.0516 (5)	0.0154 (4)	0.0018 (4)	−0.0060 (3)
Br1	0.0843 (3)	0.0436 (2)	0.0925 (3)	−0.00243 (16)	0.0188 (2)	0.02590 (17)

Geometric parameters (Å, º) top

C1—C6	1.371 (4)	C13—C14	1.386 (4)
C1—C2	1.393 (4)	C13—H13	0.9300
C1—S1	1.748 (3)	C14—N1	1.418 (3)
C2—C3	1.372 (4)	C15—N2	1.453 (4)
C2—H2	0.9300	C15—H15A	0.9700
C3—C4	1.377 (5)	C15—H15B	0.9700
C3—H3	0.9300	N2—S2	1.627 (3)
C4—C5	1.369 (5)	N2—H2A	0.874 (10)
C4—H4	0.9300	C16—C17	1.364 (5)
C5—C6	1.378 (4)	C16—C21	1.373 (4)
C5—H5	0.9300	C16—S2	1.764 (3)
C6—H6	0.9300	C17—C18	1.391 (6)
C7—C8	1.336 (4)	C17—H17	0.9300
C7—N1	1.421 (3)	C18—C19	1.361 (7)
C7—C15	1.502 (4)	C18—H18	0.9300
C8—C9	1.426 (4)	C19—C20	1.346 (7)
C8—Br1	1.868 (3)	C19—H19	0.9300
C9—C14	1.387 (4)	C20—C21	1.363 (5)
C9—C10	1.388 (4)	C20—H20	0.9300
C10—C11	1.367 (5)	C21—H21	0.9300
C10—H10	0.9300	N1—S1	1.659 (2)
C11—C12	1.380 (5)	O1—S1	1.4203 (19)
C11—H11	0.9300	O2—S1	1.416 (2)
C12—C13	1.370 (4)	O3—S2	1.419 (3)
C12—H12	0.9300	O4—S2	1.421 (3)

C6—C1—C2	121.7 (3)	N2—C15—C7	116.1 (2)
C6—C1—S1	119.4 (2)	N2—C15—H15A	108.3
C2—C1—S1	118.8 (2)	C7—C15—H15A	108.3
C3—C2—C1	118.4 (3)	N2—C15—H15B	108.3
C3—C2—H2	120.8	C7—C15—H15B	108.3
C1—C2—H2	120.8	H15A—C15—H15B	107.4
C2—C3—C4	120.2 (3)	C15—N2—S2	122.6 (2)
C2—C3—H3	119.9	C15—N2—H2A	113 (2)
C4—C3—H3	119.9	S2—N2—H2A	110 (2)
C5—C4—C3	120.7 (3)	C17—C16—C21	121.1 (3)
C5—C4—H4	119.6	C17—C16—S2	120.6 (3)
C3—C4—H4	119.6	C21—C16—S2	118.3 (2)
C4—C5—C6	120.2 (3)	C16—C17—C18	118.1 (4)
C4—C5—H5	119.9	C16—C17—H17	121.0
C6—C5—H5	119.9	C18—C17—H17	121.0
C1—C6—C5	118.8 (3)	C19—C18—C17	120.0 (4)
C1—C6—H6	120.6	C19—C18—H18	120.0
C5—C6—H6	120.6	C17—C18—H18	120.0
C8—C7—N1	107.2 (2)	C20—C19—C18	121.2 (4)
C8—C7—C15	128.6 (2)	C20—C19—H19	119.4
N1—C7—C15	123.6 (2)	C18—C19—H19	119.4
C7—C8—C9	110.9 (2)	C19—C20—C21	119.9 (4)
C7—C8—Br1	125.5 (2)	C19—C20—H20	120.1
C9—C8—Br1	123.5 (2)	C21—C20—H20	120.1
C14—C9—C10	119.8 (3)	C20—C21—C16	119.7 (4)
C14—C9—C8	106.4 (2)	C20—C21—H21	120.1
C10—C9—C8	133.7 (3)	C16—C21—H21	120.1
C11—C10—C9	118.4 (3)	C14—N1—C7	107.8 (2)
C11—C10—H10	120.8	C14—N1—S1	122.48 (17)
C9—C10—H10	120.8	C7—N1—S1	126.06 (17)
C10—C11—C12	121.3 (3)	O2—S1—O1	119.71 (12)
C10—C11—H11	119.4	O2—S1—N1	105.73 (12)
C12—C11—H11	119.4	O1—S1—N1	106.35 (11)
C13—C12—C11	121.5 (3)	O2—S1—C1	108.96 (12)
C13—C12—H12	119.3	O1—S1—C1	108.32 (12)
C11—C12—H12	119.3	N1—S1—C1	107.10 (12)
C12—C13—C14	117.3 (3)	O3—S2—O4	120.92 (16)
C12—C13—H13	121.3	O3—S2—N2	105.18 (15)
C14—C13—H13	121.3	O4—S2—N2	106.73 (15)
C13—C14—C9	121.7 (3)	O3—S2—C16	107.51 (15)
C13—C14—N1	130.6 (3)	O4—S2—C16	108.14 (16)
C9—C14—N1	107.7 (2)	N2—S2—C16	107.71 (13)

C6—C1—C2—C3	0.2 (4)	C18—C19—C20—C21	0.8 (7)
S1—C1—C2—C3	177.5 (2)	C19—C20—C21—C16	−0.8 (6)
C1—C2—C3—C4	−1.0 (5)	C17—C16—C21—C20	0.5 (5)
C2—C3—C4—C5	1.2 (5)	S2—C16—C21—C20	178.2 (3)
C3—C4—C5—C6	−0.5 (5)	C13—C14—N1—C7	178.7 (3)
C2—C1—C6—C5	0.4 (4)	C9—C14—N1—C7	0.4 (3)
S1—C1—C6—C5	−176.9 (2)	C13—C14—N1—S1	−21.7 (4)
C4—C5—C6—C1	−0.3 (5)	C9—C14—N1—S1	159.99 (19)
N1—C7—C8—C9	−0.2 (3)	C8—C7—N1—C14	−0.1 (3)
C15—C7—C8—C9	171.5 (3)	C15—C7—N1—C14	−172.3 (2)
N1—C7—C8—Br1	−175.46 (19)	C8—C7—N1—S1	−158.8 (2)
C15—C7—C8—Br1	−3.8 (4)	C15—C7—N1—S1	29.0 (4)
C7—C8—C9—C14	0.5 (3)	C14—N1—S1—O2	45.3 (2)
Br1—C8—C9—C14	175.8 (2)	C7—N1—S1—O2	−158.9 (2)
C7—C8—C9—C10	−175.7 (3)	C14—N1—S1—O1	173.6 (2)
Br1—C8—C9—C10	−0.3 (5)	C7—N1—S1—O1	−30.7 (3)
C14—C9—C10—C11	2.1 (5)	C14—N1—S1—C1	−70.8 (2)
C8—C9—C10—C11	177.8 (3)	C7—N1—S1—C1	85.0 (2)
C9—C10—C11—C12	−0.4 (5)	C6—C1—S1—O2	151.8 (2)
C10—C11—C12—C13	−1.2 (6)	C2—C1—S1—O2	−25.6 (2)
C11—C12—C13—C14	1.2 (5)	C6—C1—S1—O1	20.0 (3)
C12—C13—C14—C9	0.6 (4)	C2—C1—S1—O1	−157.4 (2)
C12—C13—C14—N1	−177.5 (3)	C6—C1—S1—N1	−94.3 (2)
C10—C9—C14—C13	−2.2 (4)	C2—C1—S1—N1	88.3 (2)
C8—C9—C14—C13	−179.0 (3)	C15—N2—S2—O3	174.6 (2)
C10—C9—C14—N1	176.3 (3)	C15—N2—S2—O4	45.0 (3)
C8—C9—C14—N1	−0.5 (3)	C15—N2—S2—C16	−70.9 (2)
C8—C7—C15—N2	−114.1 (3)	C17—C16—S2—O3	−136.9 (3)
N1—C7—C15—N2	56.3 (4)	C21—C16—S2—O3	45.3 (3)
C7—C15—N2—S2	66.0 (3)	C17—C16—S2—O4	−4.8 (3)
C21—C16—C17—C18	−0.2 (5)	C21—C16—S2—O4	177.4 (3)
S2—C16—C17—C18	−177.9 (3)	C17—C16—S2—N2	110.2 (3)
C16—C17—C18—C19	0.2 (6)	C21—C16—S2—N2	−67.5 (3)
C17—C18—C19—C20	−0.5 (7)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.87 (1)	2.17 (3)	2.795 (3)	128 (3)
C13—H13···O2	0.93	2.38	2.954 (4)	120
C21—H21···Cg2ⁱ	0.93	2.81	3.667 (3)	155

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.874 (10)	2.17 (3)	2.795 (3)	128 (3)
C13—H13···O2	0.93	2.38	2.954 (4)	120
C21—H21···Cg2ⁱ	0.93	2.81	3.667 (3)	155

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

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Volume 71| Part 10| October 2015| Pages o756-o757

doi:10.1107/S2056989015016874

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of N-{[3-bromo-1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}benzene­sulfonamide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of N-{[3-bromo-1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide