N-[(3-Bromo-1-phenyl­sulfonyl-1H-indol-2-yl)meth­yl]-4-fluoro­aniline

Yadav, C.S.; Viswanathan, V.; Kannadasan, S.; Velmurugan, D.

doi:10.1107/S241431461700147X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170147

https://doi.org/10.1107/S241431461700147X

Open

access

N-[(3-Bromo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-4-fluoroaniline

C. Suresh Yadav,^a Vijayan Viswanathan,^b Sathananthan Kannadasan ^a and Devadasan Velmurugan ^b ^*

^aDepartment of Chemistry, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: shirai2011@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 10 December 2016; accepted 28 January 2017; online 3 February 2017)

In the title compound, C₂₁H₁₆BrFN₂O₂S, the indole ring system makes dihedral angles of 87.23 (10) and 77.58 (9)° with the fluorobenzene and phenyl rings, respectively. The molecular structure is stabilized by a C—H⋯O and a C—H⋯Br intramolecular hydrogen bond, which generate S(6) and S(8) ring motifs, respectively. In the crystal, molecules are linked by C—H⋯π interactions, forming ribbons propagating along the a-axis direction. Within the ribbons, there are offset π–π interactions present involving inversion-related molecules [intercentroid distance = 3.650 (1) Å].

Keywords: crystal structure; indole; C—H⋯π interactions; offset π–π interactions; hydrogen bonding.

CCDC reference: 1530001

Structure description

Indole is an important heterocyclic system because it is built into proteins in the form of the amino acid tryptophan as well as being the basis of drugs such as indomethacin and providing the skeleton of indole alkaloids, the biologically active compounds from plants (Sharma et al., 2010 ). As part of our investigations of indole derivatives, we have undertaken the synthesis and crystal structure analysis of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The molecular structure is stabilized by a C—H⋯O and a C—H⋯Br intramolecular hydrogen bond, which generate S(6) and S(8) ring motifs, respectively (Fig. 1 and Table 1). The indole ring system (N2/C8–C15) adopts a planar conformation with a maximum deviation of 0.0340 (1) Å for atom C11. Atom F1 deviates by 0.0107 (1) Å from the plane of the benzene ring (C1–C6) to which it is attached. The mean plane of the indole ring system makes dihedral angles of 87.23 (10) and 77.58 (9)° with the fluorobenzene and phenyl (C16–C21) rings, respectively. The fluorobenzene and phenyl rings are inclined to one another by 81.44 (11)°. The indole and fluorobenzene rings are connected through the atoms N1 and C7 with torsion angle C8—C7—N1—C4 = 66.9 (3)°. Atom S1 has a distorted tetrahedral configuration. The widening of angle O1—S1—O2 = 119.87 (10) ° and narrowing of angle N2—S1—C16 = 105.53 (8)° from the ideal tetrahedral value are attributed to the Thorpe–Ingold effect (Bassindale, 1984 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of rings C1-C6 and C16–C21, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Br1	0.93	2.92	3.765 (2)	151
C12—H12⋯O1	0.93	2.38	2.957 (3)	120
C13—H13⋯Cg2ⁱ	0.93	2.90	3.8382 (3)	151
C15—H15⋯Cg4ⁱⁱ	0.93	2.72	3.6522 (2)	154
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+2, -z+1.

Figure 1
The molecular structure of the title compound, showing the atom labelling and with displacement ellipsoids drawn at 30% probability level. Hydrogen bonds are shown as dashed lines

In the crystal, molecules are linked by C—H⋯π interactions, forming ribbons propagating along the a-axis direction (Table 1 and Fig. 2). Within the ribbons there are offset π–π interactions involving inversion-related molecules [Cg3⋯Cg3ⁱⁱⁱ = 3.650 (1) Å; Cg3 is the centroid of the C10-C15 ring; interplanar distance = 3.440 (1) Å; slippage 1.22 Å; symmetry code: (iii) −x + 2, −y + 2, −z + 1].

Figure 2
A partial view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines, C—H⋯π interactions as blue dashed arrows and π–π interactions as orange dashed double arrows. H atoms not involved in these interactions have been excluded for clarity.

Synthesis and crystallization

A solution of 1-phenylsulfonyl-2-bromomethyl-3-bromoindole (1.07 g, 2.5 mmol, 1.0 equiv) and 4-fluoroaniline (0.27 g, 2.5 mmol, 1.0 equiv) in dry DMF (10 ml) containing finely powdered K₂CO₃ (0.69 g, 5.0 mmol, 2.0 equiv) was stirred at room temperature for 12 h. The reaction mixture was then poured onto ice (200 g) and the solid formed was filtered immediately and washed with an excess of water. The crude product was dried over CaCl₂ and recrystallized from ethyl acetate–hexane (1: 9) to give a half-white coloured solid in 72% yield. Block-like colourless crystals were obtained by slow evaporation of a solution in CH₃OH.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₁₆BrFN₂O₂S
M_r	459.33
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	8.1732 (5), 10.5828 (7), 12.1781 (8)
α, β, γ (°)	113.699 (1), 94.617 (1), 99.203 (1)
V (Å³)	939.81 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.33
Crystal size (mm)	0.24 × 0.19 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.753, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	11107, 4427, 3778
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.096, 1.05
No. of reflections	4427
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and SHELXL2016 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1530001

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S241431461700147X/su4110sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700147X/su4110Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461700147X/su4110Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); 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 SHELXL2016 (Sheldrick, 2015).

N-[(3-Bromo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-4-fluoroaniline top

Crystal data top

C₂₁H₁₆BrFN₂O₂S	Z = 2
M_r = 459.33	F(000) = 464
Triclinic, P1	D_x = 1.623 Mg m⁻³
a = 8.1732 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5828 (7) Å	Cell parameters from 4427 reflections
c = 12.1781 (8) Å	θ = 2.2–28.3°
α = 113.699 (1)°	µ = 2.33 mm⁻¹
β = 94.617 (1)°	T = 293 K
γ = 99.203 (1)°	Block, colourless
V = 939.81 (11) Å³	0.24 × 0.19 × 0.12 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	3778 reflections with I > 2σ(I)
ω and φ scans	R_int = 0.018
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 28.3°, θ_min = 2.2°
T_min = 0.753, T_max = 0.856	h = −10→10
11107 measured reflections	k = −13→13
4427 independent reflections	l = −15→15

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0594P)² + 0.1305P] where P = (F_o² + 2F_c²)/3
4427 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	1.0439 (3)	0.3846 (2)	0.3063 (2)	0.0524 (5)
C2	0.8963 (3)	0.4075 (2)	0.3480 (2)	0.0510 (5)
H2	0.870710	0.391539	0.415005	0.061*
C3	0.7849 (3)	0.4548 (2)	0.2890 (2)	0.0466 (4)
H3	0.684493	0.471193	0.317208	0.056*
C4	0.8213 (3)	0.47778 (19)	0.18896 (17)	0.0433 (4)
C5	0.9754 (3)	0.4538 (3)	0.1506 (2)	0.0599 (6)
H5	1.003760	0.470852	0.084643	0.072*
C6	1.0853 (3)	0.4057 (3)	0.2082 (2)	0.0613 (6)
H6	1.185730	0.387984	0.180567	0.074*
C7	0.5735 (3)	0.5820 (2)	0.17222 (19)	0.0491 (5)
H7A	0.507416	0.521160	0.201672	0.059*
H7B	0.500965	0.587821	0.108060	0.059*
C8	0.6282 (2)	0.7267 (2)	0.27416 (17)	0.0395 (4)
C9	0.6028 (2)	0.7717 (2)	0.39091 (18)	0.0401 (4)
C10	0.6911 (2)	0.9145 (2)	0.46065 (17)	0.0396 (4)
C11	0.7743 (2)	0.9561 (2)	0.38144 (16)	0.0378 (4)
C12	0.8800 (3)	1.0883 (2)	0.4218 (2)	0.0476 (5)
H12	0.936670	1.115759	0.369150	0.057*
C13	0.8966 (3)	1.1766 (2)	0.5435 (2)	0.0562 (5)
H13	0.966282	1.265694	0.572957	0.067*
C14	0.8138 (3)	1.1379 (2)	0.6233 (2)	0.0559 (5)
H14	0.827849	1.201048	0.704601	0.067*
C15	0.7107 (3)	1.0068 (2)	0.58341 (18)	0.0488 (5)
H15	0.655233	0.980097	0.636937	0.059*
C16	0.5460 (2)	0.9385 (2)	0.13481 (16)	0.0372 (4)
C17	0.5621 (3)	1.0827 (2)	0.1861 (2)	0.0470 (4)
H17	0.667034	1.142071	0.220819	0.056*
C18	0.4198 (3)	1.1384 (2)	0.1854 (2)	0.0524 (5)
H18	0.428905	1.235653	0.220589	0.063*
C19	0.2653 (3)	1.0502 (2)	0.1329 (2)	0.0493 (5)
H19	0.170302	1.088132	0.132396	0.059*
C20	0.2503 (3)	0.9069 (3)	0.0815 (2)	0.0528 (5)
H20	0.145091	0.848001	0.046733	0.063*
C21	0.3913 (3)	0.8489 (2)	0.08082 (19)	0.0476 (4)
H21	0.381825	0.751566	0.044744	0.057*
N1	0.7090 (2)	0.51720 (19)	0.12096 (15)	0.0522 (4)
H1	0.721138	0.502532	0.047600	0.063*
N2	0.73770 (19)	0.83989 (17)	0.26447 (13)	0.0383 (3)
O1	0.87084 (18)	0.9732 (2)	0.15578 (15)	0.0572 (4)
O2	0.6999 (2)	0.73241 (18)	0.03837 (13)	0.0560 (4)
F1	1.1535 (2)	0.33908 (19)	0.36508 (16)	0.0767 (4)
S1	0.72622 (6)	0.86853 (6)	0.13829 (4)	0.04184 (12)
BR1	0.47945 (3)	0.66201 (3)	0.45649 (2)	0.05848 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0500 (12)	0.0487 (11)	0.0578 (12)	0.0118 (9)	−0.0011 (10)	0.0229 (10)
C2	0.0572 (12)	0.0466 (11)	0.0526 (11)	0.0107 (9)	0.0073 (10)	0.0245 (9)
C3	0.0459 (10)	0.0389 (10)	0.0538 (11)	0.0094 (8)	0.0074 (9)	0.0183 (9)
C4	0.0498 (11)	0.0313 (9)	0.0393 (9)	0.0072 (8)	−0.0008 (8)	0.0073 (7)
C5	0.0660 (14)	0.0713 (15)	0.0523 (12)	0.0263 (12)	0.0186 (11)	0.0300 (11)
C6	0.0515 (12)	0.0690 (15)	0.0673 (15)	0.0207 (11)	0.0156 (11)	0.0285 (12)
C7	0.0475 (11)	0.0483 (11)	0.0452 (10)	0.0112 (9)	−0.0048 (9)	0.0152 (9)
C8	0.0366 (9)	0.0442 (10)	0.0396 (9)	0.0127 (7)	0.0033 (7)	0.0184 (8)
C9	0.0362 (9)	0.0464 (10)	0.0452 (10)	0.0126 (8)	0.0098 (7)	0.0246 (8)
C10	0.0378 (9)	0.0467 (10)	0.0391 (9)	0.0161 (8)	0.0069 (7)	0.0203 (8)
C11	0.0354 (8)	0.0440 (10)	0.0375 (9)	0.0138 (7)	0.0038 (7)	0.0189 (8)
C12	0.0465 (11)	0.0475 (11)	0.0542 (11)	0.0104 (8)	0.0033 (9)	0.0277 (9)
C13	0.0564 (13)	0.0419 (11)	0.0628 (13)	0.0090 (9)	−0.0057 (11)	0.0178 (10)
C14	0.0652 (14)	0.0527 (12)	0.0440 (11)	0.0217 (11)	0.0033 (10)	0.0122 (10)
C15	0.0551 (12)	0.0562 (12)	0.0380 (9)	0.0203 (10)	0.0105 (9)	0.0191 (9)
C16	0.0364 (9)	0.0482 (10)	0.0335 (8)	0.0139 (7)	0.0097 (7)	0.0212 (8)
C17	0.0415 (10)	0.0477 (11)	0.0555 (11)	0.0071 (8)	0.0031 (9)	0.0274 (9)
C18	0.0535 (12)	0.0469 (11)	0.0648 (13)	0.0168 (9)	0.0096 (10)	0.0294 (10)
C19	0.0435 (10)	0.0625 (13)	0.0545 (12)	0.0224 (9)	0.0130 (9)	0.0322 (10)
C20	0.0374 (10)	0.0606 (13)	0.0563 (12)	0.0095 (9)	0.0012 (9)	0.0219 (10)
C21	0.0459 (11)	0.0453 (11)	0.0459 (10)	0.0112 (8)	0.0022 (8)	0.0139 (9)
N1	0.0645 (11)	0.0503 (10)	0.0374 (8)	0.0234 (8)	0.0025 (8)	0.0109 (7)
N2	0.0389 (8)	0.0460 (8)	0.0344 (7)	0.0131 (6)	0.0060 (6)	0.0199 (7)
O1	0.0391 (7)	0.0892 (11)	0.0636 (9)	0.0172 (7)	0.0186 (7)	0.0494 (9)
O2	0.0713 (10)	0.0687 (10)	0.0383 (7)	0.0377 (8)	0.0178 (7)	0.0227 (7)
F1	0.0660 (9)	0.0927 (11)	0.0872 (11)	0.0341 (8)	0.0043 (8)	0.0487 (9)
S1	0.0396 (2)	0.0592 (3)	0.0377 (2)	0.0207 (2)	0.01327 (18)	0.0264 (2)
BR1	0.05446 (15)	0.06742 (17)	0.06666 (17)	0.01190 (11)	0.02033 (11)	0.03985 (13)

Geometric parameters (Å, º) top

C1—C6	1.360 (4)	C12—C13	1.379 (3)
C1—F1	1.363 (3)	C12—H12	0.9300
C1—C2	1.366 (3)	C13—C14	1.381 (4)
C2—C3	1.387 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.375 (3)
C3—C4	1.380 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.403 (3)	C16—C17	1.376 (3)
C4—N1	1.407 (3)	C16—C21	1.383 (3)
C5—C6	1.374 (3)	C16—S1	1.7562 (18)
C5—H5	0.9300	C17—C18	1.386 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—N1	1.449 (3)	C18—C19	1.374 (3)
C7—C8	1.500 (3)	C18—H18	0.9300
C7—H7A	0.9700	C19—C20	1.368 (3)
C7—H7B	0.9700	C19—H19	0.9300
C8—C9	1.351 (3)	C20—C21	1.389 (3)
C8—N2	1.427 (3)	C20—H20	0.9300
C9—C10	1.431 (3)	C21—H21	0.9300
C9—BR1	1.8712 (19)	N1—H1	0.8600
C10—C11	1.392 (3)	N2—S1	1.6799 (15)
C10—C15	1.397 (3)	O1—S1	1.4215 (17)
C11—C12	1.392 (3)	O2—S1	1.4324 (17)
C11—N2	1.427 (2)

C6—C1—F1	118.9 (2)	C14—C13—C12	122.5 (2)
C6—C1—C2	122.2 (2)	C14—C13—H13	118.7
F1—C1—C2	118.9 (2)	C12—C13—H13	118.7
C1—C2—C3	119.1 (2)	C15—C14—C13	120.5 (2)
C1—C2—H2	120.4	C15—C14—H14	119.8
C3—C2—H2	120.4	C13—C14—H14	119.8
C4—C3—C2	120.8 (2)	C14—C15—C10	118.5 (2)
C4—C3—H3	119.6	C14—C15—H15	120.7
C2—C3—H3	119.6	C10—C15—H15	120.7
C3—C4—C5	117.71 (19)	C17—C16—C21	121.15 (18)
C3—C4—N1	123.4 (2)	C17—C16—S1	118.91 (15)
C5—C4—N1	118.8 (2)	C21—C16—S1	119.94 (15)
C6—C5—C4	121.6 (2)	C16—C17—C18	119.11 (19)
C6—C5—H5	119.2	C16—C17—H17	120.4
C4—C5—H5	119.2	C18—C17—H17	120.4
C1—C6—C5	118.5 (2)	C19—C18—C17	120.2 (2)
C1—C6—H6	120.7	C19—C18—H18	119.9
C5—C6—H6	120.7	C17—C18—H18	119.9
N1—C7—C8	114.88 (17)	C20—C19—C18	120.40 (19)
N1—C7—H7A	108.5	C20—C19—H19	119.8
C8—C7—H7A	108.5	C18—C19—H19	119.8
N1—C7—H7B	108.5	C19—C20—C21	120.4 (2)
C8—C7—H7B	108.5	C19—C20—H20	119.8
H7A—C7—H7B	107.5	C21—C20—H20	119.8
C9—C8—N2	107.46 (17)	C16—C21—C20	118.8 (2)
C9—C8—C7	128.96 (19)	C16—C21—H21	120.6
N2—C8—C7	123.22 (18)	C20—C21—H21	120.6
C8—C9—C10	110.49 (17)	C4—N1—C7	121.22 (18)
C8—C9—BR1	125.55 (16)	C4—N1—H1	119.4
C10—C9—BR1	123.88 (14)	C7—N1—H1	119.4
C11—C10—C15	120.12 (19)	C11—N2—C8	107.49 (15)
C11—C10—C9	106.54 (16)	C11—N2—S1	120.22 (13)
C15—C10—C9	133.28 (19)	C8—N2—S1	122.79 (13)
C12—C11—C10	121.47 (18)	O1—S1—O2	119.87 (10)
C12—C11—N2	130.41 (18)	O1—S1—N2	106.12 (9)
C10—C11—N2	108.01 (16)	O2—S1—N2	106.04 (9)
C13—C12—C11	116.9 (2)	O1—S1—C16	109.28 (10)
C13—C12—H12	121.6	O2—S1—C16	109.01 (9)
C11—C12—H12	121.6	N2—S1—C16	105.53 (8)

C6—C1—C2—C3	−0.5 (3)	C21—C16—C17—C18	1.2 (3)
F1—C1—C2—C3	179.51 (19)	S1—C16—C17—C18	−178.91 (17)
C1—C2—C3—C4	0.4 (3)	C16—C17—C18—C19	−0.7 (3)
C2—C3—C4—C5	−1.0 (3)	C17—C18—C19—C20	0.3 (3)
C2—C3—C4—N1	175.91 (18)	C18—C19—C20—C21	−0.5 (4)
C3—C4—C5—C6	1.6 (3)	C17—C16—C21—C20	−1.4 (3)
N1—C4—C5—C6	−175.4 (2)	S1—C16—C21—C20	178.72 (17)
F1—C1—C6—C5	−178.9 (2)	C19—C20—C21—C16	1.1 (3)
C2—C1—C6—C5	1.0 (4)	C3—C4—N1—C7	21.2 (3)
C4—C5—C6—C1	−1.6 (4)	C5—C4—N1—C7	−162.0 (2)
N1—C7—C8—C9	−118.5 (2)	C8—C7—N1—C4	66.9 (3)
N1—C7—C8—N2	53.7 (3)	C12—C11—N2—C8	176.79 (19)
N2—C8—C9—C10	0.9 (2)	C10—C11—N2—C8	0.68 (19)
C7—C8—C9—C10	174.02 (18)	C12—C11—N2—S1	−36.0 (3)
N2—C8—C9—BR1	−176.08 (12)	C10—C11—N2—S1	147.90 (13)
C7—C8—C9—BR1	−3.0 (3)	C9—C8—N2—C11	−0.97 (19)
C8—C9—C10—C11	−0.5 (2)	C7—C8—N2—C11	−174.58 (16)
BR1—C9—C10—C11	176.56 (13)	C9—C8—N2—S1	−147.16 (14)
C8—C9—C10—C15	−177.6 (2)	C7—C8—N2—S1	39.2 (2)
BR1—C9—C10—C15	−0.6 (3)	C11—N2—S1—O1	47.52 (16)
C15—C10—C11—C12	0.9 (3)	C8—N2—S1—O1	−170.39 (15)
C9—C10—C11—C12	−176.67 (17)	C11—N2—S1—O2	176.02 (14)
C15—C10—C11—N2	177.44 (16)	C8—N2—S1—O2	−41.89 (17)
C9—C10—C11—N2	−0.15 (19)	C11—N2—S1—C16	−68.41 (15)
C10—C11—C12—C13	−0.8 (3)	C8—N2—S1—C16	73.69 (16)
N2—C11—C12—C13	−176.45 (18)	C17—C16—S1—O1	−20.95 (18)
C11—C12—C13—C14	0.1 (3)	C21—C16—S1—O1	158.89 (16)
C12—C13—C14—C15	0.5 (3)	C17—C16—S1—O2	−153.69 (16)
C13—C14—C15—C10	−0.4 (3)	C21—C16—S1—O2	26.15 (18)
C11—C10—C15—C14	−0.3 (3)	C17—C16—S1—N2	92.79 (16)
C9—C10—C15—C14	176.5 (2)	C21—C16—S1—N2	−87.37 (17)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of rings C1-C6 and C16–C21, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Br1	0.93	2.92	3.765 (2)	151
C12—H12···O1	0.93	2.38	2.957 (3)	120
C13—H13···Cg2ⁱ	0.93	2.90	3.8382 (3)	151
C15—H15···Cg4ⁱⁱ	0.93	2.72	3.6522 (2)	154

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

Acknowledgements

CSY thanks VIT University for support. The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection.

References

Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons. Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sharma, V., Kumar, P. & Pathak, D. (2010). J. Heterocycl. Chem. 47, 491–502. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170147

https://doi.org/10.1107/S241431461700147X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

N-[(3-Bromo-1-phenyl­sulfonyl-1H-indol-2-yl)meth­yl]-4-fluoro­aniline

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

N-[(3-Bromo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-4-fluoroaniline