1-(2-Bromo­meth­yl-1-phenyl­sulfonyl-1H-indol-3-yl)propan-1-one

Umadevi, M.; Saravanan, V.; Yamuna, R.; Mohanakrishnan, A.K.; Chakkaravarthi, G.

doi:10.1107/S1600536813031413

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1802-o1803

doi:10.1107/S1600536813031413

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1-(2-Bromomethyl-1-phenylsulfonyl-1H-indol-3-yl)propan-1-one

M. Umadevi,^a V. Saravanan,^b R. Yamuna,^c ^* A. K. Mohanakrishnan ^b and G. Chakkaravarthi ^d ^*

^aResearch Scholar (Chemistry), Bharathiyar University, Coimbatore 641 046, Tamilnadu, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com

(Received 13 November 2013; accepted 16 November 2013; online 23 November 2013)

In the title compound, C₁₈H₁₆BrNO₃S, the dihedral angle between the phenyl ring and the indole ring system is 89.91 (11)°. The molecular structure features weak C—H⋯O and C—H⋯Br hydrogen bonds. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming chains along the a-axis direction. The chains are further linked by C—H⋯π interactions, forming a layer parallel to the ab plane.

CCDC reference: 972314

Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006 ); Nieto et al. (2005 ). For related structures, see: Chakkaravarthi et al. (2008 , 2010 ). 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

C₁₈H₁₆BrNO₃S
M_r = 406.29
Monoclinic, P 2₁ /c
a = 10.2772 (7) Å
b = 8.6610 (6) Å
c = 18.8980 (14) Å
β = 90.676 (2)°
V = 1682.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.58 mm⁻¹
T = 295 K
0.38 × 0.34 × 0.30 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.397, T_max = 0.461
25944 measured reflections
7303 independent reflections
3726 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.133
S = 1.00
7303 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 1.11 e Å⁻³
Δρ_min = −0.90 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Br1	0.93	2.89	3.815 (2)	171
C13—H13⋯O2	0.93	2.39	2.978 (3)	121
C15—H15B⋯O1	0.97	2.15	2.833 (3)	126
C2—H2⋯O3ⁱ	0.93	2.59	3.191 (3)	123
C15—H15A⋯Cg3ⁱⁱ	0.97	2.74	3.486 (3)	134
C18—H18B⋯Cg2ⁱⁱⁱ	0.96	2.66	3.616 (3)	174
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z+2; (iii) -x, -y, -z+2.

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

CCDC reference: 972314

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813031413/is5323sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031413/is5323Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031413/is5323Isup3.cml

checkCIF report

Comment top

Indole derivatives exhibit antihepatitis B virus (Chai et al., 2006) and antibacterial (Nieto et al., 2005) activities. We herein report the crystal structure of the title compound (I) (Fig. 1). The bond distances of (I) are comparable with the reported similar structures (Chakkaravarthi et al., 2008, 2010). The bond angles around atom S1 show significant deviation from ideal tetrahedral value [O1—S1—O2 = 120.16 (13)° and N1—S1—C1 = 105.11 (10)°] due to Thorpe-Ignold effect (Bassindale, 1984). The sum of the bond angles around N1 (358.05°) indicates the sp² hybridization of N1 atom (Beddoes et al., 1986).

The indole ring system is planar, with the dihedral angle between the two rings (N1/C7/C8/C9/C14) and (C9–C14) is 2.00 (12)°. The phenyl ring (C1–C6) makes the dihedral angle of 89.91 (11)° with the indole ring system. The molecular structure is stabilized by weak intramolecular C—H···O and C—H···Br hydrogen bonds (Table 1). The crystal structure exhibit weak intermolecular C—H···O and C—H···π (Table 1 & Fig. 2) interactions.

Related literature top

For the biological activity of indole derivatives, see: Chai et al. (2006); Nieto et al. (2005). For related structures, see: Chakkaravarthi et al. (2008, 2010). 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

A mixture of 1-[2-methyl-1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one (15 g, 45.87 mmol) and N-bromosuccinimide (9.8 g, 55 mmol) in dry CCl₄ (250 ml) containing a catalytic amount of 2,2'-azobis(isobutyronitrile) (50 mg) was refluxed for 3 h. Then, the reaction mixture was cooled to room temperature, filtered off the floated succinimide through Na₂SO₄ pad and washed with CCl₄ (20 ml). Removal of the solvent followed by trituration of the crude product with MeOH (50 ml) gave the title compound, suitable for X-ray diffraction quality.

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 the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram of the title compound viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involving hydrogen bonding have been omitted.

1-(2-Bromomethyl-1-phenylsulfonyl-1H-indol-3-yl)propan-1-one top

Crystal data top

C₁₈H₁₆BrNO₃S	F(000) = 824
M_r = 406.29	D_x = 1.604 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5675 reflections
a = 10.2772 (7) Å	θ = 2.6–28.2°
b = 8.6610 (6) Å	µ = 2.58 mm⁻¹
c = 18.8980 (14) Å	T = 295 K
β = 90.676 (2)°	Block, colourless
V = 1682.0 (2) Å³	0.38 × 0.34 × 0.30 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	7303 independent reflections
Radiation source: fine-focus sealed tube	3726 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and ϕ scan	θ_max = 35.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
T_min = 0.397, T_max = 0.461	k = −13→13
25944 measured reflections	l = −30→30

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0528P)² + 0.8633P] where P = (F_o² + 2F_c²)/3
7303 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

C₁₈H₁₆BrNO₃S	V = 1682.0 (2) Å³
M_r = 406.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2772 (7) Å	µ = 2.58 mm⁻¹
b = 8.6610 (6) Å	T = 295 K
c = 18.8980 (14) Å	0.38 × 0.34 × 0.30 mm
β = 90.676 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	7303 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3726 reflections with I > 2σ(I)
T_min = 0.397, T_max = 0.461	R_int = 0.036
25944 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	Δρ_max = 1.11 e Å⁻³
7303 reflections	Δρ_min = −0.90 e Å⁻³
218 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.

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

	x	y	z	U_iso*/U_eq
C1	0.3590 (2)	0.2855 (3)	1.15387 (11)	0.0316 (4)
C2	0.4906 (2)	0.2669 (3)	1.14030 (14)	0.0388 (5)
H2	0.5349	0.3387	1.1130	0.047*
C3	0.5545 (2)	0.1404 (3)	1.16792 (14)	0.0478 (6)
H3	0.6429	0.1276	1.1599	0.057*
C4	0.4891 (3)	0.0341 (4)	1.20682 (14)	0.0527 (7)
H4	0.5334	−0.0508	1.2251	0.063*
C5	0.3573 (3)	0.0506 (4)	1.21952 (16)	0.0594 (8)
H5	0.3134	−0.0236	1.2456	0.071*
C6	0.2917 (2)	0.1775 (3)	1.19338 (14)	0.0468 (6)
H6	0.2035	0.1906	1.2021	0.056*
C7	0.03158 (18)	0.3688 (2)	1.08099 (11)	0.0276 (4)
C8	−0.0180 (2)	0.2867 (2)	1.02518 (11)	0.0290 (4)
C9	0.0851 (2)	0.2600 (2)	0.97521 (11)	0.0304 (4)
C10	0.0935 (2)	0.1861 (3)	0.90938 (12)	0.0407 (5)
H10	0.0217	0.1359	0.8898	0.049*
C11	0.2110 (3)	0.1894 (3)	0.87400 (14)	0.0492 (7)
H11	0.2173	0.1407	0.8303	0.059*
C12	0.3188 (3)	0.2635 (3)	0.90221 (14)	0.0491 (7)
H12	0.3957	0.2646	0.8768	0.059*
C13	0.3152 (2)	0.3356 (3)	0.96705 (13)	0.0411 (6)
H13	0.3880	0.3847	0.9861	0.049*
C14	0.19702 (19)	0.3317 (3)	1.00296 (11)	0.0306 (4)
C15	−0.0399 (2)	0.4324 (3)	1.14247 (12)	0.0358 (5)
H15A	−0.1235	0.4717	1.1264	0.043*
H15B	0.0090	0.5179	1.1625	0.043*
C16	−0.1576 (2)	0.2394 (3)	1.02006 (13)	0.0355 (5)
C17	−0.2006 (2)	0.1315 (3)	0.96217 (14)	0.0419 (6)
H17A	−0.1440	0.0418	0.9621	0.050*
H17B	−0.1922	0.1829	0.9169	0.050*
C18	−0.3408 (3)	0.0787 (4)	0.97091 (16)	0.0561 (7)
H18A	−0.3494	0.0268	1.0155	0.084*
H18B	−0.3639	0.0093	0.9332	0.084*
H18C	−0.3975	0.1668	0.9696	0.084*
N1	0.16494 (16)	0.3982 (2)	1.06867 (9)	0.0299 (4)
O1	0.21453 (16)	0.5195 (2)	1.18571 (10)	0.0523 (5)
O2	0.36972 (17)	0.5470 (2)	1.08811 (11)	0.0523 (5)
O3	−0.23528 (17)	0.2863 (3)	1.06323 (11)	0.0571 (5)
S1	0.28085 (5)	0.45547 (7)	1.12687 (3)	0.03548 (14)
Br1	−0.06733 (3)	0.27582 (4)	1.215850 (15)	0.06069 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0272 (9)	0.0409 (12)	0.0268 (10)	0.0035 (9)	−0.0028 (8)	−0.0044 (9)
C2	0.0273 (10)	0.0475 (14)	0.0417 (13)	−0.0015 (9)	0.0007 (9)	−0.0020 (11)
C3	0.0305 (11)	0.0644 (18)	0.0484 (15)	0.0119 (11)	−0.0046 (10)	−0.0013 (13)
C4	0.0490 (14)	0.0675 (19)	0.0415 (14)	0.0214 (14)	−0.0025 (12)	0.0139 (13)
C5	0.0545 (16)	0.072 (2)	0.0515 (16)	0.0105 (15)	0.0129 (13)	0.0290 (15)
C6	0.0332 (11)	0.0619 (17)	0.0456 (15)	0.0068 (11)	0.0090 (10)	0.0126 (13)
C7	0.0253 (8)	0.0293 (11)	0.0281 (10)	0.0034 (8)	0.0001 (8)	0.0040 (8)
C8	0.0285 (9)	0.0303 (11)	0.0281 (10)	0.0006 (8)	−0.0007 (8)	0.0036 (8)
C9	0.0324 (10)	0.0318 (11)	0.0270 (10)	0.0045 (8)	0.0001 (8)	0.0047 (8)
C10	0.0456 (13)	0.0457 (14)	0.0307 (12)	0.0055 (11)	−0.0012 (10)	−0.0033 (10)
C11	0.0534 (15)	0.0605 (17)	0.0339 (13)	0.0191 (13)	0.0064 (11)	−0.0038 (12)
C12	0.0409 (12)	0.0657 (18)	0.0411 (14)	0.0144 (12)	0.0138 (11)	0.0046 (13)
C13	0.0302 (10)	0.0525 (15)	0.0409 (13)	0.0053 (10)	0.0052 (10)	0.0047 (11)
C14	0.0283 (9)	0.0341 (11)	0.0294 (10)	0.0056 (8)	0.0008 (8)	0.0040 (9)
C15	0.0331 (10)	0.0424 (13)	0.0321 (11)	0.0050 (9)	0.0036 (9)	−0.0016 (10)
C16	0.0308 (10)	0.0373 (13)	0.0383 (12)	−0.0023 (9)	−0.0034 (9)	0.0044 (10)
C17	0.0404 (12)	0.0399 (14)	0.0452 (14)	−0.0030 (10)	−0.0091 (11)	0.0015 (11)
C18	0.0482 (15)	0.0594 (18)	0.0606 (18)	−0.0179 (13)	−0.0115 (13)	−0.0020 (15)
N1	0.0244 (7)	0.0356 (10)	0.0296 (9)	0.0016 (7)	−0.0013 (7)	−0.0002 (8)
O1	0.0429 (9)	0.0590 (12)	0.0548 (11)	0.0097 (8)	−0.0095 (8)	−0.0286 (9)
O2	0.0412 (9)	0.0383 (10)	0.0774 (14)	−0.0094 (8)	−0.0049 (9)	0.0062 (10)
O3	0.0341 (9)	0.0783 (14)	0.0593 (13)	−0.0117 (9)	0.0086 (8)	−0.0156 (11)
S1	0.0297 (2)	0.0333 (3)	0.0434 (3)	0.0002 (2)	−0.0058 (2)	−0.0068 (2)
Br1	0.04826 (16)	0.0928 (3)	0.04125 (16)	0.01267 (15)	0.01231 (12)	0.02479 (15)

Geometric parameters (Å, º) top

C1—C6	1.386 (3)	C11—C12	1.382 (4)
C1—C2	1.389 (3)	C11—H11	0.9300
C1—S1	1.750 (2)	C12—C13	1.376 (4)
C2—C3	1.376 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.399 (3)
C3—C4	1.361 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—N1	1.411 (3)
C4—C5	1.385 (4)	C15—Br1	1.963 (2)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.378 (4)	C15—H15B	0.9700
C5—H5	0.9300	C16—O3	1.218 (3)
C6—H6	0.9300	C16—C17	1.502 (3)
C7—C8	1.366 (3)	C17—C18	1.522 (3)
C7—N1	1.416 (2)	C17—H17A	0.9700
C7—C15	1.488 (3)	C17—H17B	0.9700
C8—C9	1.446 (3)	C18—H18A	0.9600
C8—C16	1.494 (3)	C18—H18B	0.9600
C9—C10	1.403 (3)	C18—H18C	0.9600
C9—C14	1.403 (3)	N1—S1	1.6864 (18)
C10—C11	1.387 (4)	O1—S1	1.4236 (18)
C10—H10	0.9300	O2—S1	1.4193 (19)

C6—C1—C2	121.0 (2)	C12—C13—C14	117.0 (2)
C6—C1—S1	119.62 (17)	C12—C13—H13	121.5
C2—C1—S1	119.21 (19)	C14—C13—H13	121.5
C3—C2—C1	118.9 (2)	C13—C14—C9	122.8 (2)
C3—C2—H2	120.6	C13—C14—N1	129.1 (2)
C1—C2—H2	120.6	C9—C14—N1	108.08 (17)
C4—C3—C2	120.5 (2)	C7—C15—Br1	111.86 (16)
C4—C3—H3	119.8	C7—C15—H15A	109.2
C2—C3—H3	119.8	Br1—C15—H15A	109.2
C3—C4—C5	120.9 (2)	C7—C15—H15B	109.2
C3—C4—H4	119.5	Br1—C15—H15B	109.2
C5—C4—H4	119.5	H15A—C15—H15B	107.9
C6—C5—C4	119.7 (3)	O3—C16—C8	120.1 (2)
C6—C5—H5	120.2	O3—C16—C17	120.4 (2)
C4—C5—H5	120.2	C8—C16—C17	119.5 (2)
C5—C6—C1	119.1 (2)	C16—C17—C18	112.2 (2)
C5—C6—H6	120.5	C16—C17—H17A	109.2
C1—C6—H6	120.5	C18—C17—H17A	109.2
C8—C7—N1	108.64 (18)	C16—C17—H17B	109.2
C8—C7—C15	127.79 (19)	C18—C17—H17B	109.2
N1—C7—C15	123.36 (19)	H17A—C17—H17B	107.9
C7—C8—C9	108.54 (18)	C17—C18—H18A	109.5
C7—C8—C16	122.81 (19)	C17—C18—H18B	109.5
C9—C8—C16	128.6 (2)	H18A—C18—H18B	109.5
C10—C9—C14	118.3 (2)	C17—C18—H18C	109.5
C10—C9—C8	134.9 (2)	H18A—C18—H18C	109.5
C14—C9—C8	106.79 (19)	H18B—C18—H18C	109.5
C11—C10—C9	118.8 (2)	C14—N1—C7	107.94 (17)
C11—C10—H10	120.6	C14—N1—S1	121.55 (14)
C9—C10—H10	120.6	C7—N1—S1	128.56 (14)
C12—C11—C10	121.5 (2)	O2—S1—O1	120.16 (13)
C12—C11—H11	119.3	O2—S1—N1	106.36 (11)
C10—C11—H11	119.3	O1—S1—N1	106.44 (9)
C13—C12—C11	121.6 (2)	O2—S1—C1	108.93 (11)
C13—C12—H12	119.2	O1—S1—C1	108.79 (11)
C11—C12—H12	119.2	N1—S1—C1	105.11 (10)

C6—C1—C2—C3	−1.2 (4)	N1—C7—C15—Br1	−103.6 (2)
S1—C1—C2—C3	173.4 (2)	C7—C8—C16—O3	7.0 (4)
C1—C2—C3—C4	1.2 (4)	C9—C8—C16—O3	−171.7 (2)
C2—C3—C4—C5	−0.1 (5)	C7—C8—C16—C17	−171.8 (2)
C3—C4—C5—C6	−1.0 (5)	C9—C8—C16—C17	9.5 (3)
C4—C5—C6—C1	0.9 (5)	O3—C16—C17—C18	−6.7 (4)
C2—C1—C6—C5	0.2 (4)	C8—C16—C17—C18	172.2 (2)
S1—C1—C6—C5	−174.4 (2)	C13—C14—N1—C7	177.2 (2)
N1—C7—C8—C9	0.5 (2)	C9—C14—N1—C7	−0.8 (2)
C15—C7—C8—C9	175.3 (2)	C13—C14—N1—S1	−17.4 (3)
N1—C7—C8—C16	−178.40 (19)	C9—C14—N1—S1	164.61 (15)
C15—C7—C8—C16	−3.7 (3)	C8—C7—N1—C14	0.2 (2)
C7—C8—C9—C10	−179.2 (2)	C15—C7—N1—C14	−174.9 (2)
C16—C8—C9—C10	−0.4 (4)	C8—C7—N1—S1	−163.90 (16)
C7—C8—C9—C14	−1.0 (2)	C15—C7—N1—S1	21.1 (3)
C16—C8—C9—C14	177.8 (2)	C14—N1—S1—O2	49.4 (2)
C14—C9—C10—C11	−1.1 (3)	C7—N1—S1—O2	−148.47 (19)
C8—C9—C10—C11	176.9 (2)	C14—N1—S1—O1	178.65 (18)
C9—C10—C11—C12	0.0 (4)	C7—N1—S1—O1	−19.2 (2)
C10—C11—C12—C13	0.8 (4)	C14—N1—S1—C1	−66.04 (19)
C11—C12—C13—C14	−0.5 (4)	C7—N1—S1—C1	96.1 (2)
C12—C13—C14—C9	−0.7 (4)	C6—C1—S1—O2	179.4 (2)
C12—C13—C14—N1	−178.4 (2)	C2—C1—S1—O2	4.7 (2)
C10—C9—C14—C13	1.5 (3)	C6—C1—S1—O1	46.8 (2)
C8—C9—C14—C13	−177.0 (2)	C2—C1—S1—O1	−127.98 (19)
C10—C9—C14—N1	179.7 (2)	C6—C1—S1—N1	−66.9 (2)
C8—C9—C14—N1	1.1 (2)	C2—C1—S1—N1	118.35 (19)
C8—C7—C15—Br1	82.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Br1	0.93	2.89	3.815 (2)	171
C13—H13···O2	0.93	2.39	2.978 (3)	121
C15—H15B···O1	0.97	2.15	2.833 (3)	126
C2—H2···O3ⁱ	0.93	2.59	3.191 (3)	123
C15—H15A···Cg3ⁱⁱ	0.97	2.74	3.486 (3)	134
C18—H18B···Cg2ⁱⁱⁱ	0.96	2.66	3.616 (3)	174

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Br1	0.93	2.89	3.815 (2)	171
C13—H13···O2	0.93	2.39	2.978 (3)	121
C15—H15B···O1	0.97	2.15	2.833 (3)	126
C2—H2···O3ⁱ	0.93	2.59	3.191 (3)	123
C15—H15A···Cg3ⁱⁱ	0.97	2.74	3.486 (3)	134
C18—H18B···Cg2ⁱⁱⁱ	0.96	2.66	3.616 (3)	174

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

Acknowledgements

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

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Volume 69| Part 12| December 2013| Pages o1802-o1803

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