N-(4,4′-Dibromo-[1,1′-biphen­yl]-2-yl)benzamide

Novina, J.J.; Vasuki, G.; Baheti, A.; Thomas, K.R.J.

doi:10.1107/S1600536813000597

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o222

doi:10.1107/S1600536813000597

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N-(4,4′-Dibromo-[1,1′-biphenyl]-2-yl)benzamide

J. Josephine Novina,^a G. Vasuki,^b ^* Abhishek Baheti ^c and K. R. Justin Thomas ^c

^aDepartment of Physics, Idhaya College for Women, Kumbakonam-1, India, ^bDepartment of Physics, Kunthavai Naachiar Govt. Arts College (W) (Autonomous), Thanjavur-7, India, and ^cOrganic Materials Lab, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India
^*Correspondence e-mail: vasuki.arasi@yahoo.com

(Received 6 January 2013; accepted 7 January 2013; online 12 January 2013)

In the title compound, C₁₉H₁₃Br₂NO, the dihedral angle between the rings of the biphenyl group is 53.59 (14)°. The ring of the benzamide group is inclined to the phenyl rings of the biphenyl group by 23.87 (15) and 75.89 (15)°. There are no significant intermolecular interactions in the crystal structure.

Related literature

For applications of the title compound, see: Libman & Slack (1951 ); Mandadapu et al. (2009 ); Youn & Bihn (2009 ); Yulan et al. (2010 ). For pharmacological properties of biphenyl aniline, see: Zhu et al. (2008 ). For related structures, see: Li & Cui (2011 ); Kuś et al. (2009 ); Hammond et al. (2009 ); Gowda et al. (2010 ); Novina et al. (2012 ).

Experimental

Crystal data

C₁₉H₁₃Br₂NO
M_r = 431.12
Monoclinic, P 2₁ /c
a = 9.0188 (5) Å
b = 11.6415 (9) Å
c = 16.0068 (12) Å
β = 100.737 (2)°
V = 1651.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 4.91 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.238, T_max = 0.374
16420 measured reflections
3453 independent reflections
2302 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.075
S = 1.01
3453 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000597/su2551sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000597/su2551Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813000597/su2551Isup3.cml

checkCIF report

Comment top

Biphenyl aniline, a subclass of biaryl compounds, has been recognized as a privileged structure in drug discovery. Its derivatives have been pursued as anti–phlogistic, analgesic, anti–obesity, and anti–tumor agents (Zhu et al., 2008). Amide substituted biphenyl derivatives are commonly used to develop antiparasitic agents for the treatment of African sleeping sickness disease (Libman & Slack, 1951; Mandadapu et al., 2009; Youn & Bihn, 2009; Yulan et al., 2010). Benzamides are recognized as one of the important bioactive skeletons and exhibit various potent pharmaceutical activities. As part of our studies on the substituent effects on the structures and other aspects of dibromo biphenyl derivatives, 4,4'-Dibromo-2-nitrobiphenyl (Novina et al., 2012), in the present work we report herein on the synthesis and crystal structure of the title compound.

In the molecular structure of the title compound (Fig. 1), the two benzene rings of the biphenyl group are twisted with respect to each other by 53.59 (14)°, which is similar to to the arrangement [53.52 (14)°] found in 2,5-Bis(bromomethyl)biphenyl (Kuś et al., 2009), but is somewhat larger than the angle of 45.5 (2)° found in 3,3',5,5'-Tetranitrobiphenyl (Hammond et al., 2009). The amide unit C1—N1—C13(O1)—C14 is planar [r.m.s deviation = 0.013 Å], and subtends dihedral angles of 12.38 (12)° and 32.34 (11)° respectively to the C1-C6 and C14-C19 phenyl rings. These two aromatic rings are inclined to one another by 23.87 (15)°, while rings C7-C12 and C14-C19 are inclined to one another by 75.89 (15)°. The C13═O1 and C13—N1 bond distances are 1.221 (3) and 1.360 (3) Å, respectively, showing the electron delocalization in the amide fragment. The N—H and C═O bonds in the amide group are anti to each other, similar to that observed in 2-Chloro-N-(2,3-dimethylphenyl)-benzamide (Gowda et al., 2010), and N-(3,5-Dimethoxyphenyl)benzamide (Li & Cui, 2011). The length of the bond connecting the phenyl rings, 1.489 (4) Å, is close to the standard value of 1.48 Å for a Csp²—Csp² single bond.

In the crystal, there are no significant interactions and the structure is stabilized by Van der Waals interactions (Fig. 2).

Related literature top

For applications of the title compound, see: Libman & Slack (1951); Mandadapu et al. (2009); Youn & Bihn (2009); Yulan et al. (2010). For pharmacological properties of biphenyl aniline, see: Zhu et al. (2008). For related structures, see: Li & Cui (2011); Kuś et al. (2009); Hammond et al. (2009); Gowda et al. (2010). For our studies on the substituent effects on the structures and other aspects of dibromobiphenyl derivatives, see: Novina et al. (2012).

Experimental top

To a dry THF solution of 4,4'-dibromo-[1,1'-biphenyl]-2-amine (3.27 g, 10 mmol) and triethylamine (3 ml) was added drop wise a dry THF solution (40 ml) of benzoyl chloride at 273 K. After stirring at room temperature for 20 h, the solution was poured into water (80 ml) and extracted with dichloromethane (2 × 50 ml). The combined organic extracts were dried over anhydrous Na₂SO₄ and evaporated to dryness. This gave white solid which was further recrystallized with dichloromethane-hexanes [Yield 3.0 g (70%); M.p. 443–445 K]. HRMS calcd. for C₁₉H₁₃Br₂NO [M]⁺ m/z 428.9364 found 428.9363. Spectroscopic data for the title compound is available in the archived CIF.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (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, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound viewed along the b axis.

N-(4,4'-Dibromo-[1,1'-biphenyl]-2-yl)benzamide top

Crystal data top

C₁₉H₁₃Br₂NO	F(000) = 848
M_r = 431.12	D_x = 1.734 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3453 reflections
a = 9.0188 (5) Å	θ = 2.2–26.6°
b = 11.6415 (9) Å	µ = 4.91 mm⁻¹
c = 16.0068 (12) Å	T = 293 K
β = 100.737 (2)°	Block, colourless
V = 1651.2 (2) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3453 independent reflections
Radiation source: fine-focus sealed tube	2302 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and ϕ scan	θ_max = 26.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.238, T_max = 0.374	k = −14→14
16420 measured reflections	l = −19→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0267P)² + 1.1775P] where P = (F_o² + 2F_c²)/3
3453 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₉H₁₃Br₂NO	V = 1651.2 (2) Å³
M_r = 431.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0188 (5) Å	µ = 4.91 mm⁻¹
b = 11.6415 (9) Å	T = 293 K
c = 16.0068 (12) Å	0.30 × 0.25 × 0.20 mm
β = 100.737 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3453 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2302 reflections with I > 2σ(I)
T_min = 0.238, T_max = 0.374	R_int = 0.032
16420 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.01	Δρ_max = 0.46 e Å⁻³
3453 reflections	Δρ_min = −0.49 e Å⁻³
208 parameters

Special details top

Experimental. Spectroscopic data for the title compound: IR (ν_N—H) 3399 cm^-1, 1567 cm^-1, (ν_C_═_O) 1666 cm^-1, ¹H NMR (CDCl₃, 500 MHz) δ: 8.74 (d, J = 1.5 Hz, 1 H), 7.85 (s, 1H), 7.60 (dd, J = 6.5, 2.0 Hz, 2 H), 7.59–7.61 (m, 2 H), 7.52–7.55 (m, 1 H), 7.42–7.45 (m, 2 H), 7.35 (d, J = 1.5 Hz, 1 H), 7.30 (dd, J = 6.5, 2.0 Hz, 2 H), 7.11 (d, J = 8.0 Hz, 1 H); ¹³C NMR (CDCl₃, 125 MHz) δ 165.1, 136.0, 135.8, 134.1, 133.7, 32.6, 131.1, 130.8, 130.2, 130.1, 129.0, 128.5, 127.7, 126.8, 124.6, 122.9, 122.7.

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
Br1	0.63621 (4)	0.21302 (3)	0.15668 (2)	0.06302 (13)
Br2	0.22124 (4)	1.08134 (3)	0.04697 (3)	0.07108 (15)
O1	0.1733 (2)	0.33800 (17)	−0.05842 (14)	0.0542 (6)
C1	0.3653 (3)	0.4886 (2)	0.06373 (17)	0.0342 (6)
C8	0.4769 (3)	0.7869 (2)	0.09646 (18)	0.0414 (7)
H8	0.5785	0.7681	0.1022	0.050*
C19	0.0269 (3)	0.4448 (3)	−0.2115 (2)	0.0496 (8)
H19	0.0688	0.3731	−0.2180	0.060*
N1	0.2512 (2)	0.51464 (19)	−0.00712 (14)	0.0380 (6)
H1	0.2333	0.5866	−0.0160	0.046*
C11	0.1763 (3)	0.8444 (3)	0.07935 (19)	0.0480 (8)
H11	0.0750	0.8640	0.0737	0.058*
C2	0.4251 (3)	0.3787 (2)	0.07720 (18)	0.0397 (7)
H2	0.3859	0.3185	0.0417	0.048*
C4	0.6025 (3)	0.4467 (3)	0.19891 (18)	0.0455 (8)
H4	0.6806	0.4320	0.2444	0.055*
C3	0.5430 (3)	0.3604 (3)	0.14369 (18)	0.0410 (7)
C7	0.3728 (3)	0.7005 (2)	0.10278 (17)	0.0361 (6)
C12	0.2218 (3)	0.7322 (3)	0.09524 (19)	0.0440 (7)
H12	0.1504	0.6766	0.1010	0.053*
C14	0.0602 (3)	0.5010 (2)	−0.13340 (18)	0.0372 (7)
C9	0.4329 (3)	0.8994 (2)	0.08194 (19)	0.0439 (7)
H9	0.5043	0.9562	0.0789	0.053*
C10	0.2825 (3)	0.9271 (2)	0.07198 (19)	0.0437 (7)
C5	0.5431 (3)	0.5548 (3)	0.18479 (19)	0.0455 (7)
H5	0.5831	0.6139	0.2213	0.055*
C6	0.4249 (3)	0.5796 (2)	0.11777 (17)	0.0367 (6)
C13	0.1656 (3)	0.4425 (2)	−0.06326 (18)	0.0373 (7)
C18	−0.0677 (4)	0.4950 (3)	−0.2791 (2)	0.0626 (10)
H18	−0.0875	0.4581	−0.3315	0.075*
C17	−0.1326 (4)	0.5993 (4)	−0.2690 (3)	0.0746 (11)
H17	−0.1956	0.6334	−0.3149	0.089*
C15	−0.0075 (3)	0.6061 (3)	−0.1242 (2)	0.0493 (8)
H15	0.0130	0.6446	−0.0725	0.059*
C16	−0.1055 (4)	0.6535 (3)	−0.1922 (3)	0.0664 (10)
H16	−0.1532	0.7228	−0.1855	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0675 (2)	0.0512 (2)	0.0659 (2)	0.01286 (17)	0.00079 (18)	0.01402 (17)
Br2	0.0641 (2)	0.0444 (2)	0.0985 (3)	0.00851 (17)	−0.0009 (2)	0.0004 (2)
O1	0.0578 (13)	0.0335 (12)	0.0629 (14)	−0.0026 (10)	−0.0104 (11)	−0.0010 (10)
C1	0.0326 (15)	0.0391 (16)	0.0314 (15)	−0.0046 (12)	0.0071 (12)	0.0051 (13)
C8	0.0324 (15)	0.0438 (18)	0.0471 (18)	−0.0032 (13)	0.0048 (13)	−0.0074 (15)
C19	0.0484 (18)	0.0491 (19)	0.0467 (19)	−0.0067 (15)	−0.0033 (15)	−0.0017 (16)
N1	0.0417 (13)	0.0296 (13)	0.0390 (14)	−0.0036 (10)	−0.0018 (11)	0.0029 (11)
C11	0.0359 (16)	0.054 (2)	0.052 (2)	0.0038 (15)	0.0044 (14)	−0.0088 (16)
C2	0.0421 (16)	0.0373 (16)	0.0389 (17)	−0.0044 (13)	0.0055 (14)	0.0031 (13)
C4	0.0430 (17)	0.060 (2)	0.0311 (16)	0.0009 (15)	0.0000 (14)	0.0086 (15)
C3	0.0417 (16)	0.0442 (17)	0.0382 (17)	0.0009 (14)	0.0104 (14)	0.0127 (14)
C7	0.0369 (15)	0.0385 (16)	0.0316 (15)	−0.0024 (13)	0.0035 (12)	−0.0055 (13)
C12	0.0369 (16)	0.0481 (19)	0.0473 (18)	−0.0097 (14)	0.0082 (14)	−0.0066 (15)
C14	0.0324 (14)	0.0391 (16)	0.0394 (17)	−0.0069 (12)	0.0050 (13)	0.0024 (13)
C9	0.0408 (17)	0.0397 (17)	0.0498 (19)	−0.0085 (13)	0.0052 (14)	−0.0060 (14)
C10	0.0478 (18)	0.0375 (17)	0.0428 (18)	0.0015 (14)	0.0003 (14)	−0.0059 (14)
C5	0.0442 (17)	0.0528 (19)	0.0368 (17)	−0.0030 (15)	0.0004 (14)	−0.0036 (15)
C6	0.0349 (15)	0.0421 (17)	0.0337 (16)	−0.0037 (13)	0.0083 (13)	0.0013 (13)
C13	0.0348 (15)	0.0381 (17)	0.0393 (17)	−0.0065 (12)	0.0072 (13)	0.0005 (13)
C18	0.063 (2)	0.073 (3)	0.045 (2)	−0.019 (2)	−0.0081 (18)	0.0018 (18)
C17	0.060 (2)	0.086 (3)	0.068 (3)	0.001 (2)	−0.015 (2)	0.026 (2)
C15	0.0505 (18)	0.0472 (19)	0.0496 (19)	0.0029 (15)	0.0079 (16)	0.0050 (15)
C16	0.062 (2)	0.060 (2)	0.074 (3)	0.0151 (18)	0.005 (2)	0.016 (2)

Geometric parameters (Å, º) top

Br1—C3	1.904 (3)	C4—C5	1.370 (4)
Br2—C10	1.899 (3)	C4—C3	1.379 (4)
O1—C13	1.221 (3)	C4—H4	0.9300
C1—C2	1.390 (4)	C7—C12	1.394 (4)
C1—C6	1.409 (4)	C7—C6	1.489 (4)
C1—N1	1.415 (3)	C12—H12	0.9300
C8—C9	1.376 (4)	C14—C15	1.388 (4)
C8—C7	1.393 (4)	C14—C13	1.493 (4)
C8—H8	0.9300	C9—C10	1.374 (4)
C19—C18	1.377 (4)	C9—H9	0.9300
C19—C14	1.393 (4)	C5—C6	1.395 (4)
C19—H19	0.9300	C5—H5	0.9300
N1—C13	1.360 (3)	C18—C17	1.371 (5)
N1—H1	0.8600	C18—H18	0.9300
C11—C12	1.378 (4)	C17—C16	1.362 (5)
C11—C10	1.379 (4)	C17—H17	0.9300
C11—H11	0.9300	C15—C16	1.382 (4)
C2—C3	1.374 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—H16	0.9300

C2—C1—C6	120.3 (2)	C15—C14—C19	118.9 (3)
C2—C1—N1	121.7 (2)	C15—C14—C13	123.6 (3)
C6—C1—N1	117.9 (2)	C19—C14—C13	117.5 (3)
C9—C8—C7	121.5 (3)	C10—C9—C8	119.4 (3)
C9—C8—H8	119.2	C10—C9—H9	120.3
C7—C8—H8	119.2	C8—C9—H9	120.3
C18—C19—C14	120.3 (3)	C9—C10—C11	120.8 (3)
C18—C19—H19	119.8	C9—C10—Br2	119.2 (2)
C14—C19—H19	119.8	C11—C10—Br2	119.9 (2)
C13—N1—C1	129.5 (2)	C4—C5—C6	122.4 (3)
C13—N1—H1	115.3	C4—C5—H5	118.8
C1—N1—H1	115.3	C6—C5—H5	118.8
C12—C11—C10	119.3 (3)	C5—C6—C1	117.8 (3)
C12—C11—H11	120.3	C5—C6—C7	119.5 (3)
C10—C11—H11	120.3	C1—C6—C7	122.6 (2)
C3—C2—C1	119.0 (3)	O1—C13—N1	123.7 (3)
C3—C2—H2	120.5	O1—C13—C14	121.5 (3)
C1—C2—H2	120.5	N1—C13—C14	114.8 (2)
C5—C4—C3	118.1 (3)	C17—C18—C19	119.9 (3)
C5—C4—H4	121.0	C17—C18—H18	120.1
C3—C4—H4	121.0	C19—C18—H18	120.1
C2—C3—C4	122.4 (3)	C16—C17—C18	120.5 (3)
C2—C3—Br1	119.1 (2)	C16—C17—H17	119.7
C4—C3—Br1	118.4 (2)	C18—C17—H17	119.7
C8—C7—C12	117.6 (3)	C16—C15—C14	119.9 (3)
C8—C7—C6	119.9 (2)	C16—C15—H15	120.1
C12—C7—C6	122.5 (2)	C14—C15—H15	120.1
C11—C12—C7	121.3 (3)	C17—C16—C15	120.4 (3)
C11—C12—H12	119.4	C17—C16—H16	119.8
C7—C12—H12	119.4	C15—C16—H16	119.8

C2—C1—N1—C13	11.6 (4)	C4—C5—C6—C7	−175.9 (3)
C6—C1—N1—C13	−172.7 (3)	C2—C1—C6—C5	−0.8 (4)
C6—C1—C2—C3	−0.1 (4)	N1—C1—C6—C5	−176.5 (2)
N1—C1—C2—C3	175.5 (2)	C2—C1—C6—C7	175.5 (2)
C1—C2—C3—C4	1.4 (4)	N1—C1—C6—C7	−0.2 (4)
C1—C2—C3—Br1	−174.8 (2)	C8—C7—C6—C5	51.6 (4)
C5—C4—C3—C2	−1.7 (4)	C12—C7—C6—C5	−127.9 (3)
C5—C4—C3—Br1	174.6 (2)	C8—C7—C6—C1	−124.6 (3)
C9—C8—C7—C12	−1.0 (4)	C12—C7—C6—C1	55.9 (4)
C9—C8—C7—C6	179.5 (3)	C1—N1—C13—O1	2.2 (5)
C10—C11—C12—C7	−0.9 (5)	C1—N1—C13—C14	−177.1 (2)
C8—C7—C12—C11	2.1 (4)	C15—C14—C13—O1	148.3 (3)
C6—C7—C12—C11	−178.4 (3)	C19—C14—C13—O1	−30.4 (4)
C18—C19—C14—C15	2.2 (4)	C15—C14—C13—N1	−32.3 (4)
C18—C19—C14—C13	−179.0 (3)	C19—C14—C13—N1	149.0 (3)
C7—C8—C9—C10	−1.1 (5)	C14—C19—C18—C17	−1.7 (5)
C8—C9—C10—C11	2.3 (5)	C19—C18—C17—C16	−0.7 (6)
C8—C9—C10—Br2	−177.2 (2)	C19—C14—C15—C16	−0.4 (4)
C12—C11—C10—C9	−1.3 (5)	C13—C14—C15—C16	−179.1 (3)
C12—C11—C10—Br2	178.3 (2)	C18—C17—C16—C15	2.5 (6)
C3—C4—C5—C6	0.7 (4)	C14—C15—C16—C17	−2.0 (5)
C4—C5—C6—C1	0.5 (4)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃Br₂NO
M_r	431.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.0188 (5), 11.6415 (9), 16.0068 (12)
β (°)	100.737 (2)
V (Å³)	1651.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.91
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.238, 0.374
No. of measured, independent and observed [I > 2σ(I)] reflections	16420, 3453, 2302
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.075, 1.01
No. of reflections	3453
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.49

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), PLATON (Spek, 2009).

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, IIT Madras, Chennai, for the data collection.

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