1,1′-[(2-Bromo­phen­yl)­methyl­ene]­dipyrrolidin-2-one

Li, H.-Q.; Ramachandran, G.; Satheesh, V.; Sathiyanarayanan, K.; Rathore, R.S.

doi:10.1107/S1600536812006277

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o768

doi:10.1107/S1600536812006277

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1,1′-[(2-Bromophenyl)methylene]dipyrrolidin-2-one

Hong-Qi Li,^a ^* G. Ramachandran,^b V. Satheesh,^b K. Sathiyanarayanan ^b and R. S. Rathore ^c

^aKey Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, ^bChemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, and ^cBioinformatics Infrastructure Facility, Department of Biotechnology, School of Life Sciences, University of Hyderabad, Hyderabad 500 046, India
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 12 February 2012; accepted 13 February 2012; online 17 February 2012)

In the title compound, C₁₅H₁₇BrN₂O₂, both pyrrolidinone rings adopt envelope conformations. The crystal packing is characterized by short C—Br⋯O=C interactions [Br⋯O = 3.1730 (13) Å], leading to supramolecular dimers. Intermolecular C—H⋯O and C—H⋯π interactions are also observed.

Related literature

For a related structure, see: Camus et al. (2001 ). For related references on Br⋯O interactions, see: Allen et al. (1997 ); Damodharan et al. (2004 ).

Experimental

Crystal data

C₁₅H₁₇BrN₂O₂
M_r = 337.22
Monoclinic, P 2₁ /n
a = 7.9734 (3) Å
b = 11.0788 (4) Å
c = 15.9456 (6) Å
β = 91.859 (1)°
V = 1407.82 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 123 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.593, T_max = 0.621
15532 measured reflections
4296 independent reflections
3661 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.057
S = 1.01
4296 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O2ⁱ	0.97	2.40	3.363 (2)	174
C6—H6B⋯O2ⁱ	0.97	2.59	3.528 (2)	163
C11—H11⋯O1ⁱ	0.93	2.56	3.328 (2)	140
C13—H13⋯O2ⁱⁱ	0.93	2.55	3.223 (2)	130
C8—H8B⋯Cgⁱⁱⁱ	0.97	2.75	3.6405 (19)	152
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006277/xu5471sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006277/xu5471Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006277/xu5471Isup3.cml

checkCIF report

Comment top

In the title compound, C₁₅H₁₇BrN₂O₂, both pyrrolidinone rings (N1/C2—C5; N2/C6—C9) adopt envelope conformation with C3 and C7 atoms at their flap, respectively (Fig. 1). Crystal packing is characterized by C15—Br1···O1—C5ⁱ interaction [symmetry code (i): 2 - x,1 - y,-z; Br···O = 3.1730 (13) Å, C—Br···O = 170.33 (5)°] leading to molecular dimers (Fig. 2). Intermolecular C—H···O and C—H···π interactions additionally stabilize the packing (Table 1).

Related literature top

For a related structure, see: Camus et al. (2001). For related references on Br···O interactions, see: Allen et al. (1997); Damodharan et al. (2004).

Experimental top

In a dry 100 ml Erlenmeyer flask 2-pyrrolidone (10 mmol), benzaldehyde (10 mmol), iodine (15 mol %) and dichloromethane (DCM; 15 ml) were taken. The reaction mixture was stirred at room temperature (25°C) for one hour. The reaction was monitored by TLC and after the completion of reaction iodine utilized was set free from the product by treating it with aqueous sodium thiosulfate solution and extracted into DCM (2 X 20 ml). The crude reaction mixture was purified by column chromatography on silica gel using ethyl acetate/hexane as the eluents. Final yields: 82%; m.p. 354 (1)°K. Suitable single crystals for data collection were grown from ethanol and tetrahydrofuran (THF) mixture (1:1).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of (I) with non-H atoms shown as probability ellipsoids at 30% levels (Farrugia, 1997). H atoms radii are on an arbitrary scale.
	Fig. 2. Molecular dimers via Br···O interaction.

1,1'-[(2-Bromophenyl)methylene]dipyrrolidin-2-one top

Crystal data top

C₁₅H₁₇BrN₂O₂	F(000) = 688
M_r = 337.22	D_x = 1.591 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 354(1) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.9734 (3) Å	Cell parameters from 840 reflections
b = 11.0788 (4) Å	θ = 2.1–24.0°
c = 15.9456 (6) Å	µ = 2.92 mm⁻¹
β = 91.859 (1)°	T = 123 K
V = 1407.82 (9) Å³	Block, colorless
Z = 4	0.20 × 0.18 × 0.18 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4296 independent reflections
Radiation source: fine-focus sealed tube	3661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 30.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.593, T_max = 0.621	k = −14→15
15532 measured reflections	l = −22→22

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0228P)² + 0.7592P] where P = (F_o² + 2F_c²)/3
4296 reflections	(Δ/σ)_max = 0.002
181 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₅H₁₇BrN₂O₂	V = 1407.82 (9) Å³
M_r = 337.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9734 (3) Å	µ = 2.92 mm⁻¹
b = 11.0788 (4) Å	T = 123 K
c = 15.9456 (6) Å	0.20 × 0.18 × 0.18 mm
β = 91.859 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4296 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3661 reflections with I > 2σ(I)
T_min = 0.593, T_max = 0.621	R_int = 0.027
15532 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.01	Δρ_max = 0.43 e Å⁻³
4296 reflections	Δρ_min = −0.38 e Å⁻³
181 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	0.86332 (17)	0.68852 (12)	0.18659 (8)	0.0138 (3)
H1	0.9215	0.6106	0.1871	0.017*
C2	0.75434 (19)	0.81209 (13)	0.05820 (9)	0.0182 (3)
H2A	0.8600	0.8379	0.0356	0.022*
H2B	0.7103	0.8762	0.0925	0.022*
C3	0.62857 (19)	0.77622 (15)	−0.01195 (9)	0.0218 (3)
H3A	0.5146	0.7938	0.0037	0.026*
H3B	0.6515	0.8186	−0.0636	0.026*
C4	0.6548 (2)	0.64047 (14)	−0.02201 (9)	0.0223 (3)
H4A	0.5493	0.6001	−0.0355	0.027*
H4B	0.7329	0.6238	−0.0659	0.027*
C5	0.72546 (18)	0.60005 (14)	0.06225 (9)	0.0178 (3)
C6	0.58936 (18)	0.75537 (13)	0.25328 (9)	0.0180 (3)
H6A	0.5089	0.7226	0.2124	0.022*
H6B	0.6087	0.8398	0.2406	0.022*
C7	0.5283 (2)	0.73979 (15)	0.34296 (10)	0.0231 (3)
H7A	0.5544	0.8108	0.3765	0.028*
H7B	0.4080	0.7264	0.3425	0.028*
C8	0.62238 (18)	0.62932 (14)	0.37781 (9)	0.0191 (3)
H8A	0.6604	0.6428	0.4355	0.023*
H8B	0.5511	0.5584	0.3756	0.023*
C9	0.76951 (17)	0.61425 (12)	0.32157 (8)	0.0151 (3)
C10	0.99547 (17)	0.78631 (13)	0.19871 (8)	0.0139 (2)
C11	0.98318 (18)	0.87298 (13)	0.26151 (9)	0.0169 (3)
H11	0.8926	0.8708	0.2968	0.020*
C12	1.10341 (19)	0.96235 (14)	0.27229 (9)	0.0201 (3)
H12	1.0935	1.0188	0.3150	0.024*
C13	1.23820 (19)	0.96825 (14)	0.21989 (10)	0.0220 (3)
H13	1.3175	1.0293	0.2267	0.026*
C14	1.25446 (18)	0.88301 (14)	0.15741 (10)	0.0200 (3)
H14	1.3442	0.8867	0.1217	0.024*
C15	1.13587 (18)	0.79196 (13)	0.14840 (9)	0.0161 (3)
N1	0.77437 (15)	0.69982 (10)	0.10618 (7)	0.0147 (2)
N2	0.74562 (15)	0.68714 (10)	0.25438 (7)	0.0146 (2)
O1	0.73991 (15)	0.49624 (10)	0.08795 (7)	0.0253 (2)
O2	0.89131 (13)	0.54791 (10)	0.33318 (7)	0.0210 (2)
Br1	1.171997 (18)	0.670483 (13)	0.066302 (9)	0.01925 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0145 (6)	0.0132 (6)	0.0136 (6)	0.0009 (5)	0.0010 (5)	0.0000 (5)
C2	0.0219 (7)	0.0148 (7)	0.0178 (6)	0.0008 (5)	−0.0014 (5)	0.0013 (5)
C3	0.0200 (7)	0.0269 (8)	0.0184 (7)	0.0013 (6)	−0.0022 (5)	0.0011 (6)
C4	0.0262 (8)	0.0241 (8)	0.0166 (7)	−0.0066 (6)	0.0000 (6)	−0.0032 (6)
C5	0.0182 (6)	0.0188 (7)	0.0166 (6)	−0.0046 (5)	0.0040 (5)	−0.0032 (5)
C6	0.0148 (6)	0.0160 (7)	0.0233 (7)	0.0036 (5)	0.0030 (5)	0.0013 (5)
C7	0.0227 (7)	0.0219 (8)	0.0252 (8)	0.0032 (6)	0.0089 (6)	−0.0016 (6)
C8	0.0208 (7)	0.0197 (7)	0.0171 (6)	−0.0026 (6)	0.0044 (5)	−0.0004 (5)
C9	0.0175 (6)	0.0125 (6)	0.0154 (6)	−0.0029 (5)	0.0006 (5)	−0.0011 (5)
C10	0.0146 (6)	0.0133 (6)	0.0136 (6)	0.0007 (5)	−0.0014 (5)	0.0015 (5)
C11	0.0179 (7)	0.0174 (7)	0.0155 (6)	0.0002 (5)	0.0000 (5)	0.0000 (5)
C12	0.0238 (7)	0.0169 (7)	0.0191 (7)	−0.0015 (6)	−0.0049 (5)	−0.0020 (5)
C13	0.0181 (7)	0.0195 (7)	0.0279 (8)	−0.0034 (6)	−0.0049 (6)	0.0025 (6)
C14	0.0135 (6)	0.0227 (8)	0.0238 (7)	0.0003 (6)	0.0011 (5)	0.0049 (6)
C15	0.0157 (6)	0.0167 (6)	0.0160 (6)	0.0033 (5)	0.0000 (5)	0.0013 (5)
N1	0.0178 (6)	0.0123 (5)	0.0140 (5)	−0.0013 (4)	−0.0008 (4)	−0.0006 (4)
N2	0.0142 (5)	0.0140 (6)	0.0158 (5)	0.0018 (4)	0.0029 (4)	0.0015 (4)
O1	0.0359 (6)	0.0154 (5)	0.0246 (6)	−0.0066 (5)	0.0020 (5)	−0.0017 (4)
O2	0.0206 (5)	0.0194 (5)	0.0229 (5)	0.0047 (4)	0.0015 (4)	0.0052 (4)
Br1	0.02074 (8)	0.01928 (8)	0.01803 (7)	0.00452 (6)	0.00520 (5)	−0.00019 (6)

Geometric parameters (Å, º) top

C1—N1	1.4504 (17)	C7—C8	1.531 (2)
C1—N2	1.4545 (17)	C7—H7A	0.9700
C1—C10	1.5192 (19)	C7—H7B	0.9700
C1—H1	0.9800	C8—C9	1.5088 (19)
C2—N1	1.4664 (18)	C8—H8A	0.9700
C2—C3	1.530 (2)	C8—H8B	0.9700
C2—H2A	0.9700	C9—O2	1.2272 (17)
C2—H2B	0.9700	C9—N2	1.3501 (18)
C3—C4	1.528 (2)	C10—C11	1.393 (2)
C3—H3A	0.9700	C10—C15	1.3997 (19)
C3—H3B	0.9700	C11—C12	1.385 (2)
C4—C5	1.508 (2)	C11—H11	0.9300
C4—H4A	0.9700	C12—C13	1.384 (2)
C4—H4B	0.9700	C12—H12	0.9300
C5—O1	1.2251 (19)	C13—C14	1.382 (2)
C5—N1	1.3589 (18)	C13—H13	0.9300
C6—N2	1.4569 (18)	C14—C15	1.387 (2)
C6—C7	1.535 (2)	C14—H14	0.9300
C6—H6A	0.9700	C15—Br1	1.9059 (14)
C6—H6B	0.9700

N1—C1—N2	110.43 (11)	C8—C7—H7B	110.7
N1—C1—C10	111.61 (11)	C6—C7—H7B	110.7
N2—C1—C10	111.99 (11)	H7A—C7—H7B	108.8
N1—C1—H1	107.5	C9—C8—C7	104.72 (12)
N2—C1—H1	107.5	C9—C8—H8A	110.8
C10—C1—H1	107.5	C7—C8—H8A	110.8
N1—C2—C3	102.63 (11)	C9—C8—H8B	110.8
N1—C2—H2A	111.2	C7—C8—H8B	110.8
C3—C2—H2A	111.2	H8A—C8—H8B	108.9
N1—C2—H2B	111.2	O2—C9—N2	124.65 (13)
C3—C2—H2B	111.2	O2—C9—C8	127.11 (13)
H2A—C2—H2B	109.2	N2—C9—C8	108.25 (12)
C4—C3—C2	104.12 (12)	C11—C10—C15	117.22 (13)
C4—C3—H3A	110.9	C11—C10—C1	121.22 (12)
C2—C3—H3A	110.9	C15—C10—C1	121.55 (12)
C4—C3—H3B	110.9	C12—C11—C10	121.16 (13)
C2—C3—H3B	110.9	C12—C11—H11	119.4
H3A—C3—H3B	109.0	C10—C11—H11	119.4
C5—C4—C3	104.31 (12)	C13—C12—C11	120.45 (14)
C5—C4—H4A	110.9	C13—C12—H12	119.8
C3—C4—H4A	110.9	C11—C12—H12	119.8
C5—C4—H4B	110.9	C14—C13—C12	119.72 (14)
C3—C4—H4B	110.9	C14—C13—H13	120.1
H4A—C4—H4B	108.9	C12—C13—H13	120.1
O1—C5—N1	124.68 (14)	C13—C14—C15	119.48 (14)
O1—C5—C4	127.23 (13)	C13—C14—H14	120.3
N1—C5—C4	108.08 (12)	C15—C14—H14	120.3
N2—C6—C7	103.15 (12)	C14—C15—C10	121.90 (13)
N2—C6—H6A	111.1	C14—C15—Br1	117.84 (11)
C7—C6—H6A	111.1	C10—C15—Br1	120.24 (11)
N2—C6—H6B	111.1	C5—N1—C1	120.62 (12)
C7—C6—H6B	111.1	C5—N1—C2	113.36 (12)
H6A—C6—H6B	109.1	C1—N1—C2	125.19 (11)
C8—C7—C6	105.16 (11)	C9—N2—C1	121.21 (11)
C8—C7—H7A	110.7	C9—N2—C6	114.74 (11)
C6—C7—H7A	110.7	C1—N2—C6	123.90 (11)

N1—C2—C3—C4	−26.53 (15)	C1—C10—C15—Br1	−3.48 (18)
C2—C3—C4—C5	25.03 (15)	O1—C5—N1—C1	5.5 (2)
C3—C4—C5—O1	166.88 (15)	C4—C5—N1—C1	−173.64 (12)
C3—C4—C5—N1	−14.00 (16)	O1—C5—N1—C2	175.60 (14)
N2—C6—C7—C8	−19.18 (15)	C4—C5—N1—C2	−3.55 (16)
C6—C7—C8—C9	18.77 (16)	N2—C1—N1—C5	−91.10 (15)
C7—C8—C9—O2	168.80 (14)	C10—C1—N1—C5	143.64 (12)
C7—C8—C9—N2	−11.29 (16)	N2—C1—N1—C2	100.04 (15)
N1—C1—C10—C11	115.42 (14)	C10—C1—N1—C2	−25.22 (18)
N2—C1—C10—C11	−8.97 (18)	C3—C2—N1—C5	19.40 (16)
N1—C1—C10—C15	−65.71 (16)	C3—C2—N1—C1	−171.04 (12)
N2—C1—C10—C15	169.89 (12)	O2—C9—N2—C1	2.8 (2)
C15—C10—C11—C12	1.3 (2)	C8—C9—N2—C1	−177.13 (12)
C1—C10—C11—C12	−179.76 (13)	O2—C9—N2—C6	178.53 (13)
C10—C11—C12—C13	0.8 (2)	C8—C9—N2—C6	−1.39 (16)
C11—C12—C13—C14	−1.2 (2)	N1—C1—N2—C9	141.19 (13)
C12—C13—C14—C15	−0.5 (2)	C10—C1—N2—C9	−93.76 (15)
C13—C14—C15—C10	2.7 (2)	N1—C1—N2—C6	−34.15 (17)
C13—C14—C15—Br1	−175.86 (11)	C10—C1—N2—C6	90.89 (15)
C11—C10—C15—C14	−3.0 (2)	C7—C6—N2—C9	13.31 (16)
C1—C10—C15—C14	178.04 (13)	C7—C6—N2—C1	−171.07 (12)
C11—C10—C15—Br1	175.43 (10)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2ⁱ	0.97	2.40	3.363 (2)	174
C6—H6B···O2ⁱ	0.97	2.59	3.528 (2)	163
C11—H11···O1ⁱ	0.93	2.56	3.328 (2)	140
C13—H13···O2ⁱⁱ	0.93	2.55	3.223 (2)	130
C8—H8B···Cgⁱⁱⁱ	0.97	2.75	3.6405 (19)	152

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇BrN₂O₂
M_r	337.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	7.9734 (3), 11.0788 (4), 15.9456 (6)
β (°)	91.859 (1)
V (Å³)	1407.82 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.593, 0.621
No. of measured, independent and observed [I > 2σ(I)] reflections	15532, 4296, 3661
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.057, 1.01
No. of reflections	4296
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.38

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2ⁱ	0.97	2.40	3.363 (2)	174
C6—H6B···O2ⁱ	0.97	2.59	3.528 (2)	163
C11—H11···O1ⁱ	0.93	2.56	3.328 (2)	140
C13—H13···O2ⁱⁱ	0.93	2.55	3.223 (2)	130
C8—H8B···Cgⁱⁱⁱ	0.97	2.75	3.6405 (19)	152

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

RSR thanks CSIR, New Delhi, for funding under the scientist's pool scheme and BIF, University of Hyderabad, for computational resources.

References

Allen, F. H., Lommerse, J. P. M., Hoy, V. J., Howard, J. A. K. & Desiraju, G. R. (1997). Acta Cryst. B53, 1006–1016. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Camus, F., Norberg, B., Bourry, A., Rigo, B. & Durant, F. (2001). Acta Cryst. E57, o439–o440. Web of Science CSD CrossRef IUCr Journals Google Scholar
Damodharan, L., Pattabhi, V., Behera, M. & Kotha, S. (2004). J. Mol. Struct. 705, 101–106. Web of Science CSD CrossRef CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Page o768

doi:10.1107/S1600536812006277

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