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

Ramathilagam, C.; Umarani, P.R.; Saravanan, V.; Mohanakrishnan, A.K.; Gunasekaran, B.; Manivannan, V.

doi:10.1107/S1600536814002864

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o295-o296

doi:10.1107/S1600536814002864

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

C. Ramathilagam,^a P. R. Umarani,^b V. Saravanan,^c A. K. Mohanakrishnan,^c B. Gunasekaran ^d and V. Manivannan ^e ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, ^bDepartment of Physics, Kundavai Nachiyar Govt College for Women, Thanjavur 613 007, India, ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

(Received 19 January 2014; accepted 7 February 2014; online 15 February 2014)

In the title compound, C₁₇H₁₄BrNO₃S, the phenyl ring makes a dihedral angle of 89.78 (16)° with the plane of the indole ring system. The terminal Br atom and the methyl group are disordered over two sets of sites, with site occupancies of 0.860 (2) and 0.140 (2). In the crystal, molecules are linked into a chain along the b-axis direction by weak C—H⋯O hydrogen bonds. The chains are further linked by C—H⋯π interactions, forming layers parallel to the bc plane.

CCDC reference: 985849

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ); Singh et al. (2000 ); Pomarnacka & Kozlarska-Kedra (2003 ); Srivastava & Pandeya (2011 ). For related structures, see: Umadevi et al. (2013 ); Kanchanadevi et al. (2014 ).

Experimental

Crystal data

C₁₇H₁₄BrNO₃S
M_r = 392.26
Monoclinic, P 2₁ /c
a = 8.7539 (3) Å
b = 10.9968 (4) Å
c = 17.5801 (7) Å
β = 99.231 (2)°
V = 1670.43 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.60 mm⁻¹
T = 295 K
0.35 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.416, T_max = 0.522
15009 measured reflections
4141 independent reflections
2334 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.149
S = 1.03
4141 reflections
222 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.51 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
C8—H8⋯O1ⁱ	0.93	2.57	3.312 (4)	137
C10—H10⋯O1ⁱ	0.93	2.44	3.280 (4)	150
C12—H12⋯Cg2ⁱⁱ	0.93	2.72	3.528 (2)	146
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Supporting information

CCDC reference: 985849

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814002864/is5339sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002864/is5339Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814002864/is5339Isup3.cml

checkCIF report

Comment top

Indole derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). These derivatives also exhibit antimicrobial, antibiotic, analgesic, anticancer and anti-HIV (Pomarnacka & Kozlarska-Kedra, 2003; Srivastava & Pandeya, 2011) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Umadevi et al., 2013; Kanchanadevi et al., 2014). The phenyl ring makes a dihedral angle of 89.78 (16)° with the indole ring system. The terminal bromine atom and the methyl group are disordered over two positions with site occupancies of 0.860 (2) and 0.140 (2). The sum of bond angles around the atom N1 [356.7 (3) °] indicates sp² hybridized state of atom N1 in the molecule. The crystal packing is controlled by weak C—H···O and C—H···π interactions (Table 1).

Related literature top

For the biological activity of indole derivatives, see: Andreani et al. (2001); Singh et al. (2000); Pomarnacka & Kozlarska-Kedra (2003); Srivastava & Pandeya (2011). For related structures, see: Umadevi et al. (2013); Kanchanadevi et al. (2014).

Experimental top

A solution of 1-[1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one (1 g, 3.194 mmol) and PTT (phenyltrimethylammonium tribromide) (1.32 g, 3.514 mmol) in dry THF (20 ml) was stirred at room temperature for 3 h. After completion of the reaction (monitored by TLC), it was poured into crushed ice (100 g). The solid obtained was filtered and washed with MeOH (5 ml) to afford 2-bromo-1-[1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one (1.14 g, yield 91%; melting point 130–132 °C).

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: 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. The packing diagram of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₇H₁₄BrNO₃S	F(000) = 792
M_r = 392.26	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4350 reflections
a = 8.7539 (3) Å	θ = 2.2–28.4°
b = 10.9968 (4) Å	µ = 2.60 mm⁻¹
c = 17.5801 (7) Å	T = 295 K
β = 99.231 (2)°	Block, yellow
V = 1670.43 (11) Å³	0.35 × 0.25 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4141 independent reflections
Radiation source: fine-focus sealed tube	2334 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 0 pixels mm^-1	θ_max = 28.5°, θ_min = 2.2°
ω and φ scans	h = −11→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→14
T_min = 0.416, T_max = 0.522	l = −21→23
15009 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0673P)² + 0.7073P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4141 reflections	Δρ_max = 0.41 e Å⁻³
222 parameters	Δρ_min = −0.51 e Å⁻³
5 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (9)

Crystal data top

C₁₇H₁₄BrNO₃S	V = 1670.43 (11) Å³
M_r = 392.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7539 (3) Å	µ = 2.60 mm⁻¹
b = 10.9968 (4) Å	T = 295 K
c = 17.5801 (7) Å	0.35 × 0.25 × 0.25 mm
β = 99.231 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4141 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2334 reflections with I > 2σ(I)
T_min = 0.416, T_max = 0.522	R_int = 0.034
15009 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	5 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
4141 reflections	Δρ_min = −0.51 e Å⁻³
222 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.7170 (3)	0.2542 (3)	0.30787 (16)	0.0382 (7)
C2	0.6804 (4)	0.1348 (3)	0.28691 (18)	0.0480 (8)
H2	0.7480	0.0850	0.2655	0.058*
C3	0.5365 (4)	0.0944 (3)	0.2998 (2)	0.0558 (9)
H3	0.5071	0.0148	0.2870	0.067*
C4	0.4359 (4)	0.1688 (3)	0.3310 (2)	0.0627 (10)
H4	0.3398	0.1387	0.3380	0.075*
C5	0.4753 (4)	0.2878 (3)	0.3522 (2)	0.0552 (9)
H5	0.4072	0.3373	0.3735	0.066*
C6	0.6184 (3)	0.3308 (3)	0.34090 (16)	0.0392 (7)
C7	0.6963 (3)	0.4468 (2)	0.35599 (16)	0.0391 (7)
C8	0.8349 (3)	0.4370 (2)	0.33195 (16)	0.0375 (7)
H8	0.9074	0.4992	0.3341	0.045*
C9	0.8963 (3)	0.3192 (3)	0.15480 (17)	0.0427 (7)
C10	0.9085 (4)	0.4343 (3)	0.12403 (19)	0.0587 (9)
H10	0.9658	0.4947	0.1527	0.070*
C11	0.8349 (5)	0.4573 (4)	0.0508 (2)	0.0803 (12)
H11	0.8417	0.5339	0.0292	0.096*
C12	0.7501 (5)	0.3665 (4)	0.0088 (2)	0.0820 (13)
H12	0.6992	0.3830	−0.0407	0.098*
C13	0.7405 (5)	0.2530 (4)	0.0393 (2)	0.0804 (13)
H13	0.6845	0.1926	0.0101	0.096*
C14	0.8121 (4)	0.2279 (3)	0.1120 (2)	0.0614 (9)
H14	0.8050	0.1508	0.1329	0.074*
C15	0.6362 (4)	0.5538 (3)	0.39046 (19)	0.0511 (8)
C16	0.7409 (4)	0.6635 (2)	0.40341 (9)	0.0651 (10)
H16A	0.8186	0.6547	0.3694	0.078*	0.860 (2)
H16B	0.7916	0.6656	0.3576	0.078*	0.140 (2)
Br1	0.84813 (7)	0.65595 (6)	0.50680 (4)	0.0973 (3)	0.860 (2)
C17	0.6681 (10)	0.7883 (4)	0.3880 (5)	0.0539 (15)	0.860 (2)
H17A	0.7036	0.8411	0.4307	0.081*	0.860 (2)
H17B	0.5575	0.7812	0.3817	0.081*	0.860 (2)
H17C	0.6973	0.8215	0.3419	0.081*	0.860 (2)
Br1A	0.6298 (11)	0.8071 (6)	0.3977 (7)	0.132 (4)	0.140 (2)
C17A	0.875 (2)	0.6591 (18)	0.4701 (12)	0.0539 (15)	0.140 (2)
H17D	0.9557	0.7124	0.4596	0.081*	0.140 (2)
H17E	0.9138	0.5775	0.4763	0.081*	0.140 (2)
H17F	0.8396	0.6846	0.5166	0.081*	0.140 (2)
N1	0.8539 (3)	0.3213 (2)	0.30363 (13)	0.0384 (6)
O1	1.0168 (3)	0.16368 (19)	0.25653 (14)	0.0591 (6)
O2	1.1079 (2)	0.3760 (2)	0.27067 (13)	0.0526 (6)
O3	0.5058 (3)	0.5548 (2)	0.40600 (18)	0.0778 (8)
S1	0.98775 (9)	0.29060 (7)	0.24862 (4)	0.0422 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0438 (16)	0.0389 (15)	0.0298 (16)	0.0014 (13)	−0.0003 (12)	0.0057 (12)
C2	0.059 (2)	0.0392 (17)	0.0421 (19)	−0.0028 (14)	−0.0019 (15)	0.0011 (13)
C3	0.060 (2)	0.0464 (18)	0.056 (2)	−0.0136 (17)	−0.0088 (16)	0.0034 (16)
C4	0.0454 (19)	0.065 (2)	0.074 (3)	−0.0139 (18)	−0.0001 (17)	0.0101 (19)
C5	0.0441 (18)	0.058 (2)	0.063 (2)	0.0016 (16)	0.0069 (15)	0.0098 (17)
C6	0.0413 (16)	0.0405 (15)	0.0340 (16)	0.0009 (13)	0.0004 (12)	0.0080 (12)
C7	0.0454 (16)	0.0353 (15)	0.0355 (16)	0.0031 (13)	0.0034 (12)	0.0027 (12)
C8	0.0464 (17)	0.0298 (14)	0.0357 (16)	−0.0021 (12)	0.0047 (12)	−0.0002 (11)
C9	0.0470 (17)	0.0435 (17)	0.0393 (17)	0.0018 (13)	0.0115 (13)	−0.0037 (13)
C10	0.083 (2)	0.0438 (19)	0.047 (2)	−0.0007 (17)	0.0053 (18)	−0.0021 (15)
C11	0.118 (4)	0.063 (2)	0.056 (3)	0.003 (2)	0.004 (2)	0.010 (2)
C12	0.097 (3)	0.107 (4)	0.037 (2)	−0.008 (3)	−0.004 (2)	−0.001 (2)
C13	0.099 (3)	0.098 (3)	0.042 (2)	−0.033 (3)	0.008 (2)	−0.012 (2)
C14	0.078 (2)	0.061 (2)	0.047 (2)	−0.0192 (19)	0.0146 (18)	−0.0042 (17)
C15	0.057 (2)	0.051 (2)	0.047 (2)	0.0062 (16)	0.0141 (16)	0.0018 (14)
C16	0.080 (3)	0.051 (2)	0.070 (3)	−0.0090 (18)	0.029 (2)	−0.0180 (17)
Br1	0.0956 (5)	0.0997 (5)	0.0870 (5)	−0.0029 (3)	−0.0142 (3)	−0.0100 (3)
C17	0.067 (4)	0.023 (2)	0.071 (4)	0.016 (2)	0.008 (3)	0.009 (2)
Br1A	0.118 (6)	0.078 (3)	0.192 (7)	0.027 (3)	0.004 (4)	−0.038 (4)
C17A	0.067 (4)	0.023 (2)	0.071 (4)	0.016 (2)	0.008 (3)	0.009 (2)
N1	0.0432 (14)	0.0363 (13)	0.0356 (14)	−0.0015 (10)	0.0062 (10)	−0.0010 (10)
O1	0.0659 (15)	0.0400 (12)	0.0727 (17)	0.0185 (10)	0.0151 (12)	0.0072 (10)
O2	0.0369 (11)	0.0555 (13)	0.0640 (15)	−0.0048 (10)	0.0040 (10)	−0.0037 (11)
O3	0.0651 (17)	0.0646 (16)	0.111 (2)	0.0071 (13)	0.0367 (16)	−0.0143 (15)
S1	0.0431 (4)	0.0378 (4)	0.0458 (5)	0.0067 (3)	0.0078 (3)	0.0012 (3)

Geometric parameters (Å, º) top

C1—C2	1.387 (4)	C12—C13	1.366 (6)
C1—C6	1.398 (4)	C12—H12	0.9300
C1—N1	1.420 (4)	C13—C14	1.359 (5)
C2—C3	1.388 (5)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.379 (5)	C15—O3	1.216 (4)
C3—H3	0.9300	C15—C16	1.511 (4)
C4—C5	1.389 (5)	C16—C17	1.5190 (10)
C4—H4	0.9300	C16—C17A	1.520 (5)
C5—C6	1.382 (4)	C16—Br1A	1.849 (4)
C5—H5	0.9300	C16—Br1	1.9092 (10)
C6—C7	1.450 (4)	C16—H16A	0.9800
C7—C8	1.352 (4)	C16—H16B	0.9800
C7—C15	1.460 (4)	C17—H17A	0.9600
C8—N1	1.386 (3)	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600
C9—C10	1.388 (4)	C17A—H17D	0.9600
C9—C14	1.392 (5)	C17A—H17E	0.9600
C9—S1	1.743 (3)	C17A—H17F	0.9600
C10—C11	1.368 (5)	N1—S1	1.669 (2)
C10—H10	0.9300	O1—S1	1.422 (2)
C11—C12	1.384 (6)	O2—S1	1.417 (2)
C11—H11	0.9300

C2—C1—C6	123.3 (3)	C13—C14—C9	119.1 (3)
C2—C1—N1	129.7 (3)	C13—C14—H14	120.5
C6—C1—N1	107.0 (2)	C9—C14—H14	120.5
C1—C2—C3	115.9 (3)	O3—C15—C7	121.0 (3)
C1—C2—H2	122.0	O3—C15—C16	121.8 (3)
C3—C2—H2	122.0	C7—C15—C16	117.1 (3)
C4—C3—C2	121.9 (3)	C15—C16—C17	117.9 (4)
C4—C3—H3	119.0	C15—C16—C17A	117.7 (10)
C2—C3—H3	119.0	C15—C16—Br1A	111.9 (4)
C3—C4—C5	121.3 (3)	C17A—C16—Br1A	113.8 (6)
C3—C4—H4	119.4	C15—C16—Br1	107.61 (19)
C5—C4—H4	119.4	C17—C16—Br1	109.7 (4)
C6—C5—C4	118.4 (3)	C15—C16—H16A	107.0
C6—C5—H5	120.8	C17—C16—H16A	107.0
C4—C5—H5	120.8	Br1—C16—H16A	107.0
C5—C6—C1	119.2 (3)	C15—C16—H16B	103.8
C5—C6—C7	133.2 (3)	C17A—C16—H16B	103.8
C1—C6—C7	107.6 (2)	Br1A—C16—H16B	103.8
C8—C7—C6	107.0 (2)	C16—C17—H17A	109.5
C8—C7—C15	126.5 (3)	C16—C17—H17B	109.5
C6—C7—C15	126.5 (3)	H17A—C17—H17B	109.5
C7—C8—N1	110.6 (2)	C16—C17—H17C	109.5
C7—C8—H8	124.7	H17A—C17—H17C	109.5
N1—C8—H8	124.7	H17B—C17—H17C	109.5
C10—C9—C14	121.0 (3)	C16—C17A—H17D	109.5
C10—C9—S1	118.7 (2)	C16—C17A—H17E	109.5
C14—C9—S1	120.3 (2)	H17D—C17A—H17E	109.5
C11—C10—C9	118.8 (3)	C16—C17A—H17F	109.5
C11—C10—H10	120.6	H17D—C17A—H17F	109.5
C9—C10—H10	120.6	H17E—C17A—H17F	109.5
C10—C11—C12	120.0 (4)	C8—N1—C1	107.9 (2)
C10—C11—H11	120.0	C8—N1—S1	122.02 (19)
C12—C11—H11	120.0	C1—N1—S1	127.03 (19)
C13—C12—C11	120.7 (4)	O2—S1—O1	120.71 (14)
C13—C12—H12	119.6	O2—S1—N1	105.46 (12)
C11—C12—H12	119.6	O1—S1—N1	105.86 (13)
C14—C13—C12	120.4 (4)	O2—S1—C9	110.36 (14)
C14—C13—H13	119.8	O1—S1—C9	108.50 (14)
C12—C13—H13	119.8	N1—S1—C9	104.67 (13)

C6—C1—C2—C3	0.7 (4)	C6—C7—C15—C16	177.8 (2)
N1—C1—C2—C3	178.7 (3)	O3—C15—C16—C17	−37.3 (5)
C1—C2—C3—C4	0.5 (5)	C7—C15—C16—C17	140.8 (4)
C2—C3—C4—C5	−1.1 (5)	O3—C15—C16—C17A	106.8 (12)
C3—C4—C5—C6	0.4 (5)	C7—C15—C16—C17A	−75.1 (12)
C4—C5—C6—C1	0.8 (4)	O3—C15—C16—Br1A	−27.8 (5)
C4—C5—C6—C7	−179.8 (3)	C7—C15—C16—Br1A	150.3 (4)
C2—C1—C6—C5	−1.4 (4)	O3—C15—C16—Br1	87.4 (3)
N1—C1—C6—C5	−179.7 (2)	C7—C15—C16—Br1	−94.5 (3)
C2—C1—C6—C7	179.1 (3)	C7—C8—N1—C1	1.7 (3)
N1—C1—C6—C7	0.7 (3)	C7—C8—N1—S1	163.2 (2)
C5—C6—C7—C8	−179.2 (3)	C2—C1—N1—C8	−179.7 (3)
C1—C6—C7—C8	0.3 (3)	C6—C1—N1—C8	−1.5 (3)
C5—C6—C7—C15	0.7 (5)	C2—C1—N1—S1	20.1 (4)
C1—C6—C7—C15	−179.8 (3)	C6—C1—N1—S1	−161.7 (2)
C6—C7—C8—N1	−1.3 (3)	C8—N1—S1—O2	28.1 (2)
C15—C7—C8—N1	178.9 (3)	C1—N1—S1—O2	−174.2 (2)
C14—C9—C10—C11	0.7 (5)	C8—N1—S1—O1	157.1 (2)
S1—C9—C10—C11	−179.1 (3)	C1—N1—S1—O1	−45.2 (3)
C9—C10—C11—C12	0.0 (6)	C8—N1—S1—C9	−88.4 (2)
C10—C11—C12—C13	−0.8 (7)	C1—N1—S1—C9	69.3 (2)
C11—C12—C13—C14	1.1 (7)	C10—C9—S1—O2	−21.3 (3)
C12—C13—C14—C9	−0.4 (6)	C14—C9—S1—O2	158.9 (3)
C10—C9—C14—C13	−0.4 (5)	C10—C9—S1—O1	−155.7 (3)
S1—C9—C14—C13	179.3 (3)	C14—C9—S1—O1	24.6 (3)
C8—C7—C15—O3	175.7 (3)	C10—C9—S1—N1	91.7 (3)
C6—C7—C15—O3	−4.1 (5)	C14—C9—S1—N1	−88.0 (3)
C8—C7—C15—C16	−2.4 (4)

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
C8—H8···O1ⁱ	0.93	2.57	3.312 (4)	137
C10—H10···O1ⁱ	0.93	2.44	3.280 (4)	150
C12—H12···Cg2ⁱⁱ	0.93	2.72	3.528 (2)	146

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

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
C8—H8···O1ⁱ	0.93	2.57	3.312 (4)	137
C10—H10···O1ⁱ	0.93	2.44	3.280 (4)	150
C12—H12···Cg2ⁱⁱ	0.93	2.72	3.528 (2)	146

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

Acknowledgements

CR acknowledges AMET University management, India, for their kind support.

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Volume 70| Part 3| March 2014| Pages o295-o296

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