2-(4-Meth­oxy­phen­yl)-1-phenyl-1H-benzimidazole

Mohandas, T.; Jayamoorthy, K.; Jayabharathi, J.; Sakthivel, P.

doi:10.1107/S1600536813001566

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o269-o270

doi:10.1107/S1600536813001566

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2-(4-Methoxyphenyl)-1-phenyl-1H-benzimidazole

T. Mohandas,^a K. Jayamoorthy,^b J. Jayabharathi ^b and P. Sakthivel ^c ^*

^aShri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli 621 105, India, ^bDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Tamilnadu, India, and ^cDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India
^*Correspondence e-mail: sakthi2udc@gmail.com

(Received 20 November 2012; accepted 16 January 2013; online 23 January 2013)

In the title compound, C₂₀H₁₆N₂O, the 1H-benzimidazole ring forms dihedral angles of 48.00 (6) and 64.48 (6)°, respectively with the benzene and phenyl rings, which are inclined to one another by 58.51 (7)°. In the crystal, weak C—H⋯π interactions are the only intermolecular interactions present.

Related literature

For background to benzimidazole derivatives, see: Mason et al. (1999 ). For their biological activities such as antimicrobial & anticancer, antidiabetic, antifungal, anti HIV and antiviral, see: Demirayak et al. (2002 ); Minoura et al. (2004 ); Pawar et al. (2004 ); Rao et al. (2003 ); Tomei et al. (2003 ). For their action as polymerase and transcriptase inhibitors, see: Beaulieu et al. (2004 ; Morningstar et al. (2007 ); Roth et al. (1997 ); For other related studies, see: Jayabharathi et al. (2012 )

Experimental

Crystal data

C₂₀H₁₆N₂O
M_r = 300.35
Monoclinic, P 2₁ /c
a = 12.3220 (3) Å
b = 7.3030 (2) Å
c = 18.2450 (3) Å
β = 108.909 (1)°
V = 1553.22 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.956, T_max = 0.999
13787 measured reflections
2728 independent reflections
2283 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.092
S = 1.03
2728 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C2–C7 and C9–C14 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg2ⁱ	0.93	2.86	3.5361 (15)	130
C13—H13⋯Cg3ⁱⁱ	0.93	2.83	3.4594 (16)	126
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536813001566/go2077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001566/go2077Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001566/go2077Isup3.cml

checkCIF report

Comment top

The benzimidazole core is classified by medicinal chemists as one of the 'privileged substructures' for drug design,in light of the affinity they display towards a variety of enzymes and protein receptors (Mason et al.,1999).

The synthesis of benzimidazoles has received much attention owing to the varied biological activity such as antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), antiHIV (Rao et al., 2003), antidiabetic (Minoura et al., 2004), antimicrobial and anticancer (Demirayak et al., 2002), properties exhibited by a number of derivatives of these compounds.

Benzimidazole derivatives possess antioxidant activities (Jayabharathi et al.,2012).

They have emerged as potent non nucleoside inhibitors of HIV-1 reverse transcriptase (Roth et al.,1997, Morningstar et al.,2007)

It also acts as a specific inhibitors of the NS5B polymerase of the hepatitis C virus (HCV) (Beaulieu, et al., 2004).

The molecular structure of (I), is shown in Fig.1. The (N1/N2/C8—C14) 1H-benzimidazole ring is planar. It forms dihedral angles of 48.00 (6)° and 64.48 (6)° with the mean planes of the C2—C7 and C15—C20 phenyl rings respectively.

The C1—O1—C2—C7 and C3—C2—O1—C1 torsion angles are 2.8 (2)° and -176.42 (14)° respectively.

A C6—H6···π interaction involving the phenyl ring of methoxybenzene at the symmetry code [1 - x,1/2 + y,1/2 - z] and C13—H13···π interaction involving the benzene ring of benzimidazole at the symmetry code [2 - x,1/2 + y,1/2 - z] are also found.

Related literature top

For background to benzimidazole derivatives, see: Mason et al. (1999). For their biological activities such as antimicrobial & anticancer, antidiabetic, antifungal, anti HIV and antiviral, see: Demirayak et al. (2002); Minoura et al. (2004); Pawar et al. (2004); Rao et al. (2003); Tomei et al. (2003). For their action as polymerase and transcriptase inhibitors, see: Beaulieu et al. (2004;Morningstar et al. (2007); Roth et al. (1997); For other related studies, see:Jayabharathi et al. (2012)

Experimental top

To pure N-phenyl-0-phenylenediamine(17 mmol,3.128 g) in ethanol(10 ml), 4-methoxy benzaldehyde(17 mmol,2.1 ml) and ammonium acetate(3 g) was added for about 1 h while maintaining the temperature at 80°C. The reaction mixture was refluxed and the completion of reaction was monitored by TLC, finally the reactants extracted with dichloromethane. The solid separated was purified by column chromatography using petroleum ether as the eluent.Yield:2.65 g(50%) from which it was crystallized.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and 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: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure and labelling scheme for (I) with displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I) is shown. Intermolecular hydrogen bonds are shown as dashed lines.

2-(4-Methoxyphenyl)-1-phenyl-1H-benzimidazole top

Crystal data top

C₂₀H₁₆N₂O	F(000) = 632
M_r = 300.35	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6267 reflections
a = 12.3220 (3) Å	θ = 2.8–31.8°
b = 7.3030 (2) Å	µ = 0.08 mm⁻¹
c = 18.2450 (3) Å	T = 293 K
β = 108.909 (1)°	Block, colourless
V = 1553.22 (6) Å³	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2728 independent reflections
Radiation source: fine-focus sealed tube	2283 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scan	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
T_min = 0.956, T_max = 0.999	k = −8→8
13787 measured reflections	l = −21→21

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0421P)² + 0.3566P] where P = (F_o² + 2F_c²)/3
2728 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₁₆N₂O	V = 1553.22 (6) Å³
M_r = 300.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3220 (3) Å	µ = 0.08 mm⁻¹
b = 7.3030 (2) Å	T = 293 K
c = 18.2450 (3) Å	0.30 × 0.30 × 0.20 mm
β = 108.909 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2728 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2283 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.999	R_int = 0.024
13787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	Δρ_max = 0.11 e Å⁻³
2728 reflections	Δρ_min = −0.21 e Å⁻³
209 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.15098 (14)	0.1529 (3)	0.11631 (12)	0.0752 (5)
H1A	0.1582	0.0917	0.1642	0.113*
H1B	0.0756	0.1323	0.0803	0.113*
H1C	0.1629	0.2819	0.1256	0.113*
C2	0.34701 (11)	0.10389 (19)	0.12724 (8)	0.0448 (3)
C3	0.42477 (12)	0.0429 (2)	0.09213 (8)	0.0486 (4)
H3	0.3983	−0.0131	0.0438	0.058*
C4	0.54039 (12)	0.0648 (2)	0.12827 (7)	0.0450 (3)
H4	0.5916	0.0255	0.1037	0.054*
C5	0.58222 (11)	0.14511 (18)	0.20131 (7)	0.0385 (3)
C6	0.50382 (12)	0.20005 (19)	0.23664 (8)	0.0443 (3)
H6	0.5302	0.2506	0.2860	0.053*
C7	0.38733 (12)	0.1813 (2)	0.20007 (8)	0.0477 (3)
H7	0.3360	0.2209	0.2245	0.057*
C8	0.70531 (11)	0.17362 (18)	0.24035 (7)	0.0375 (3)
C9	0.87357 (11)	0.18293 (18)	0.32458 (7)	0.0404 (3)
C10	0.96985 (13)	0.1720 (2)	0.39081 (8)	0.0513 (4)
H10	0.9646	0.1228	0.4366	0.062*
C11	1.07235 (13)	0.2354 (2)	0.38684 (9)	0.0557 (4)
H11	1.1373	0.2294	0.4306	0.067*
C12	1.08135 (13)	0.3089 (2)	0.31854 (9)	0.0546 (4)
H12	1.1523	0.3504	0.3178	0.066*
C13	0.98813 (12)	0.3218 (2)	0.25235 (8)	0.0468 (3)
H13	0.9940	0.3716	0.2069	0.056*
C14	0.88502 (11)	0.25677 (18)	0.25688 (7)	0.0377 (3)
C15	0.74297 (10)	0.32860 (18)	0.12689 (7)	0.0365 (3)
C16	0.78572 (13)	0.2560 (2)	0.07224 (7)	0.0478 (4)
H16	0.8363	0.1576	0.0845	0.057*
C17	0.75247 (15)	0.3317 (2)	−0.00127 (8)	0.0589 (4)
H17	0.7807	0.2833	−0.0387	0.071*
C18	0.67873 (15)	0.4765 (3)	−0.01939 (8)	0.0626 (5)
H18	0.6565	0.5259	−0.0690	0.075*
C19	0.63744 (13)	0.5492 (2)	0.03560 (9)	0.0601 (4)
H19	0.5877	0.6488	0.0233	0.072*
C20	0.66926 (11)	0.4754 (2)	0.10932 (8)	0.0479 (4)
H20	0.6411	0.5245	0.1466	0.057*
O1	0.23425 (8)	0.08312 (16)	0.08496 (6)	0.0636 (3)
N1	0.77587 (9)	0.24986 (15)	0.20301 (5)	0.0375 (3)
N2	0.76084 (9)	0.13147 (17)	0.31277 (6)	0.0438 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0447 (6)	0.0665 (8)	0.0712 (7)	−0.0034 (5)	0.0074 (5)	−0.0040 (6)
N1	0.0387 (6)	0.0421 (6)	0.0310 (5)	−0.0019 (5)	0.0105 (4)	0.0038 (4)
N2	0.0489 (7)	0.0512 (7)	0.0316 (5)	0.0002 (5)	0.0134 (5)	0.0035 (5)
C1	0.0459 (9)	0.0666 (12)	0.1100 (15)	0.0005 (8)	0.0207 (9)	−0.0018 (11)
C2	0.0426 (7)	0.0394 (8)	0.0483 (8)	−0.0036 (6)	0.0091 (6)	0.0057 (6)
C3	0.0548 (8)	0.0520 (9)	0.0370 (7)	−0.0121 (7)	0.0121 (6)	−0.0045 (6)
C4	0.0504 (8)	0.0507 (9)	0.0382 (7)	−0.0071 (7)	0.0203 (6)	−0.0039 (6)
C5	0.0442 (7)	0.0388 (7)	0.0336 (6)	−0.0036 (6)	0.0142 (5)	0.0030 (5)
C6	0.0505 (8)	0.0461 (8)	0.0377 (7)	−0.0018 (6)	0.0164 (6)	−0.0038 (6)
C7	0.0478 (8)	0.0461 (8)	0.0532 (8)	0.0027 (7)	0.0220 (7)	−0.0007 (7)
C8	0.0443 (7)	0.0389 (7)	0.0320 (6)	−0.0010 (6)	0.0160 (5)	0.0002 (5)
C9	0.0468 (8)	0.0394 (8)	0.0333 (6)	0.0038 (6)	0.0105 (6)	−0.0006 (5)
C10	0.0566 (9)	0.0547 (9)	0.0376 (7)	0.0092 (7)	0.0080 (6)	0.0033 (6)
C11	0.0471 (8)	0.0577 (10)	0.0498 (8)	0.0081 (7)	−0.0015 (7)	−0.0036 (7)
C12	0.0417 (8)	0.0514 (9)	0.0656 (10)	−0.0010 (7)	0.0103 (7)	−0.0015 (8)
C13	0.0460 (8)	0.0442 (8)	0.0496 (8)	−0.0006 (6)	0.0147 (6)	0.0032 (6)
C14	0.0405 (7)	0.0351 (7)	0.0360 (6)	0.0029 (6)	0.0103 (5)	0.0005 (5)
C15	0.0380 (7)	0.0403 (7)	0.0301 (6)	−0.0067 (6)	0.0095 (5)	0.0032 (5)
C16	0.0587 (9)	0.0471 (9)	0.0419 (7)	−0.0050 (7)	0.0225 (7)	0.0000 (6)
C17	0.0781 (11)	0.0663 (11)	0.0376 (8)	−0.0233 (9)	0.0260 (7)	−0.0047 (7)
C18	0.0695 (10)	0.0707 (12)	0.0367 (8)	−0.0261 (9)	0.0024 (7)	0.0136 (8)
C19	0.0506 (9)	0.0592 (10)	0.0594 (9)	−0.0021 (8)	0.0024 (7)	0.0211 (8)
C20	0.0455 (8)	0.0510 (9)	0.0461 (7)	0.0003 (7)	0.0136 (6)	0.0050 (7)

Geometric parameters (Å, º) top

O1—C1	1.421 (2)	C15—C20	1.374 (2)
O1—C2	1.3616 (18)	C16—C17	1.3842 (19)
N1—C8	1.3835 (17)	C17—C18	1.363 (3)
N1—C14	1.3859 (17)	C18—C19	1.371 (2)
N1—C15	1.4349 (15)	C19—C20	1.383 (2)
N2—C8	1.3126 (16)	C1—H1A	0.9599
N2—C9	1.3868 (18)	C1—H1B	0.9599
C2—C3	1.387 (2)	C1—H1C	0.9600
C2—C7	1.380 (2)	C3—H3	0.9301
C3—C4	1.371 (2)	C4—H4	0.9299
C4—C5	1.3930 (18)	C6—H6	0.9300
C5—C6	1.383 (2)	C7—H7	0.9301
C5—C8	1.4666 (19)	C10—H10	0.9301
C6—C7	1.380 (2)	C11—H11	0.9299
C9—C10	1.395 (2)	C12—H12	0.9302
C9—C14	1.3962 (18)	C13—H13	0.9301
C10—C11	1.369 (2)	C16—H16	0.9298
C11—C12	1.394 (2)	C17—H17	0.9299
C12—C13	1.374 (2)	C18—H18	0.9301
C13—C14	1.384 (2)	C19—H19	0.9297
C15—C16	1.3759 (19)	C20—H20	0.9301

C1—O1—C2	117.99 (13)	C18—C19—C20	120.33 (15)
C8—N1—C14	106.60 (10)	C15—C20—C19	119.28 (13)
C8—N1—C15	127.76 (11)	O1—C1—H1A	109.47
C14—N1—C15	125.22 (11)	O1—C1—H1B	109.47
C8—N2—C9	105.19 (11)	O1—C1—H1C	109.47
O1—C2—C3	115.69 (12)	H1A—C1—H1B	109.48
O1—C2—C7	125.03 (13)	H1A—C1—H1C	109.47
C3—C2—C7	119.28 (13)	H1B—C1—H1C	109.47
C2—C3—C4	120.41 (13)	C2—C3—H3	119.80
C3—C4—C5	120.90 (13)	C4—C3—H3	119.80
C4—C5—C6	118.05 (13)	C3—C4—H4	119.56
C4—C5—C8	121.88 (13)	C5—C4—H4	119.55
C6—C5—C8	120.07 (12)	C5—C6—H6	119.33
C5—C6—C7	121.34 (13)	C7—C6—H6	119.33
C2—C7—C6	119.99 (14)	C2—C7—H7	120.01
N1—C8—N2	112.60 (12)	C6—C7—H7	120.00
N1—C8—C5	122.28 (11)	C9—C10—H10	120.82
N2—C8—C5	125.12 (12)	C11—C10—H10	120.81
N2—C9—C10	130.33 (12)	C10—C11—H11	119.36
N2—C9—C14	110.52 (11)	C12—C11—H11	119.33
C10—C9—C14	119.16 (13)	C11—C12—H12	119.14
C9—C10—C11	118.37 (13)	C13—C12—H12	119.12
C10—C11—C12	121.31 (15)	C12—C13—H13	121.75
C11—C12—C13	121.75 (15)	C14—C13—H13	121.74
C12—C13—C14	116.50 (13)	C15—C16—H16	120.49
N1—C14—C9	105.09 (12)	C17—C16—H16	120.46
N1—C14—C13	131.99 (12)	C16—C17—H17	119.69
C9—C14—C13	122.91 (12)	C18—C17—H17	119.68
N1—C15—C16	119.51 (12)	C17—C18—H18	120.02
N1—C15—C20	119.77 (11)	C19—C18—H18	120.00
C16—C15—C20	120.72 (12)	C18—C19—H19	119.83
C15—C16—C17	119.05 (14)	C20—C19—H19	119.83
C16—C17—C18	120.63 (15)	C15—C20—H20	120.35
C17—C18—C19	119.98 (14)	C19—C20—H20	120.37

C1—O1—C2—C3	−176.41 (14)	C8—C5—C6—C7	177.52 (13)
C1—O1—C2—C7	2.8 (2)	C4—C5—C8—N1	47.29 (19)
C15—N1—C8—N2	−173.11 (12)	C4—C5—C8—N2	−132.70 (15)
C14—N1—C8—C5	179.73 (12)	C4—C5—C6—C7	−1.9 (2)
C8—N1—C14—C9	0.04 (14)	C6—C5—C8—N2	47.9 (2)
C8—N1—C15—C16	−120.52 (15)	C5—C6—C7—C2	1.0 (2)
C14—N1—C15—C16	67.90 (18)	C14—C9—C10—C11	0.3 (2)
C8—N1—C15—C20	59.48 (18)	C10—C9—C14—C13	−0.6 (2)
C14—N1—C15—C20	−112.11 (15)	N2—C9—C14—N1	0.19 (15)
C15—N1—C8—C5	6.9 (2)	C10—C9—C14—N1	−179.49 (12)
C15—N1—C14—C9	173.11 (12)	N2—C9—C10—C11	−179.29 (14)
C8—N1—C14—C13	−178.74 (15)	N2—C9—C14—C13	179.12 (13)
C15—N1—C14—C13	−5.7 (2)	C9—C10—C11—C12	−0.2 (2)
C14—N1—C8—N2	−0.28 (15)	C10—C11—C12—C13	0.3 (2)
C8—N2—C9—C10	179.28 (14)	C11—C12—C13—C14	−0.5 (2)
C9—N2—C8—C5	−179.62 (13)	C12—C13—C14—N1	179.23 (14)
C9—N2—C8—N1	0.39 (15)	C12—C13—C14—C9	0.6 (2)
C8—N2—C9—C14	−0.35 (15)	N1—C15—C16—C17	179.30 (13)
C7—C2—C3—C4	−2.1 (2)	C16—C15—C20—C19	0.5 (2)
C3—C2—C7—C6	1.0 (2)	C20—C15—C16—C17	−0.7 (2)
O1—C2—C7—C6	−178.14 (13)	N1—C15—C20—C19	−179.51 (13)
O1—C2—C3—C4	177.13 (13)	C15—C16—C17—C18	0.2 (2)
C2—C3—C4—C5	1.2 (2)	C16—C17—C18—C19	0.5 (3)
C3—C4—C5—C8	−178.60 (13)	C17—C18—C19—C20	−0.7 (3)
C3—C4—C5—C6	0.8 (2)	C18—C19—C20—C15	0.2 (2)
C6—C5—C8—N1	−132.09 (14)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C9–C14 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg2ⁱ	0.93	2.86	3.5361 (15)	130
C13—H13···Cg3ⁱⁱ	0.93	2.83	3.4594 (16)	126

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₂O
M_r	300.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.3220 (3), 7.3030 (2), 18.2450 (3)
β (°)	108.909 (1)
V (Å³)	1553.22 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.956, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	13787, 2728, 2283
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.092, 1.03
No. of reflections	2728
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.21

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C2–C7 and C9–C14 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg2ⁱ	0.9300	2.8604	3.5361 (15)	130
C13—H13···Cg3ⁱⁱ	0.9300	2.8268	3.4594 (16)	126

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

References

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o269-o270

doi:10.1107/S1600536813001566

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