1,2-Diphenyl-1H-benzimidazole

Rosepriya, S.; Thiruvalluvar, A.; Jayamoorthy, K.; Jayabharathi, J.; Öztürk Yildirim, S.; Butcher, R.J.

doi:10.1107/S1600536812044960

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3283

doi:10.1107/S1600536812044960

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1,2-Diphenyl-1H-benzimidazole

S. Rosepriya,^a A. Thiruvalluvar,^a ^* K. Jayamoorthy,^b J. Jayabharathi,^b Sema Öztürk Yildirim ^c,^d and R. J. Butcher ^c

^aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 27 October 2012; accepted 30 October 2012; online 3 November 2012)

In the title molecule, C₁₉H₁₄N₂, the benzimidazole unit is close to being planar [maximum deviation = 0.0102 (6) Å] and forms dihedral angles of 55.80 (2) and 40.67 (3)° with the adjacent phenyl rings; the dihedral angle between the phenyl rings is 62.37 (3)°. In the crystal, one C—H⋯N hydrogen bond and three weak C—H⋯π interactions involving the fused benzene ring and the imidazole ring are observed, leading to a three-dimensional architecture.

Related literature

For the use of benzoimidazoles and phenanthroimidazoles as light-emitting devices and dye-sensitized solar cells, see: Fang et al. (2007 ); Ge et al. (2008 ); Lai et al. (2008 ); Shin et al. (2007 ); Tsai et al. (2007 ). For a closely related crystal structure, see: Jayamoorthy et al. (2012 ).

Experimental

Crystal data

C₁₉H₁₄N₂
M_r = 270.32
Monoclinic, C 2/c
a = 10.1878 (3) Å
b = 16.6399 (4) Å
c = 17.4959 (5) Å
β = 106.205 (3)°
V = 2848.13 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 123 K
0.60 × 0.40 × 0.35 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.957, T_max = 0.974
25253 measured reflections
7296 independent reflections
5803 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.137
S = 1.06
7296 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 fused benzene ring and Cg1 is the centroid of the N1/C2/N3/C9/C8 imidazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N3ⁱ	0.93	2.62	3.4829 (11)	154
C16—H16⋯Cg2ⁱⁱ	0.93	2.68	3.4843 (9)	146
C22—H22⋯Cg1ⁱⁱⁱ	0.93	2.91	3.3966 (9)	114
C23—H23⋯Cg2ⁱⁱⁱ	0.93	2.83	3.4609 (9)	126
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x, y, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812044960/hg5265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044960/hg5265Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812044960/hg5265Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812044960/hg5265Isup4.cml

checkCIF report

Comment top

Fused imidazole derivatives such as benzoimidazoles and phenanthroimidazoles [Fang et al., (2007), Ge et al., (2008), Lai et al., (2008)] have been used in the fabrication of light-emitting devices, employing them as electron-transporting layer and as sensitizers in dye-sensitized solar cells [Shin et al., (2007), Tsai et al., (2007)] due to their wide optical absorption, bright luminescence and bipolar transport characteristics. Since our research group is working in organic light emitting devices, we are interested to use the title compound as ligand for synthesizing Ir(III) complexes. Jayamoorthy et al., (2012) have reported a closely related crystal structure of 2-(4-Fluorophenyl)-1-phenyl-1H-benzimidazole.

In the title molecule, C₁₉H₁₄N₂ (Fig. 1), the benzimidazole unit is almost planar [maximum deviation = 0.0102 (6) Å for C2]. The dihedral angles between the planes of the benzimidazole and the phenyl ring at N1 and the phenyl at C2 are 55.80 (2) and 40.67 (3)°, respectively. The dihedral angle between the planes of the adjacent phenyl rings is 62.37 (3)°. Intermolecular C14—H14···N3 hydrogen bond and weak C16—H16···π interaction involving the fused benzene ring, C22—H22···π interaction involving the imidazole ring and C23—H23···π interaction involving the fused benzene ring are found in the crystal structure (Fig. 2, Table 1).

Related literature top

For the use of benzoimidazoles and phenanthroimidazoles as light-emitting devices and dye-sensitized solar cells, see: Fang et al. (2007); Ge et al. (2008); Lai et al. (2008); Shin et al. (2007); Tsai et al. (2007). For a closely related crystal structure, see: Jayamoorthy et al. (2012).

Experimental top

The pure N-phenyl-o-phenylenediamine (3.128 g, 17 mmol) in ethanol (10 ml), benzaldehyde (1.72 ml, 17 mmol) and ammonium acetate (3 g) was added about 1 h by maintaining the temperature at 353 K. The reaction mixture was refluxed for appropriate time and the completion of reaction was monitored by TLC, finally the reaction extracted with dichloromethane. The solid separated was purified by column chromatography using petroleum ether: ethyl acetate as the eluent. Yield: 2.49 g (50%). The title compound was dissolved in acetonitrile and allowed to slow evaporation for two days to obtain crystals suitable for X-ray diffraction studies.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

1,2-Diphenyl-1H-benzimidazole top

Crystal data top

C₁₉H₁₄N₂	F(000) = 1136
M_r = 270.32	D_x = 1.261 Mg m⁻³
Monoclinic, C2/c	Melting point: 380 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 10.1878 (3) Å	Cell parameters from 6755 reflections
b = 16.6399 (4) Å	θ = 3.4–37.7°
c = 17.4959 (5) Å	µ = 0.08 mm⁻¹
β = 106.205 (3)°	T = 123 K
V = 2848.13 (14) Å³	Block, colourless
Z = 8	0.60 × 0.40 × 0.35 mm

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	7296 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5803 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.5081 pixels mm^-1	θ_max = 37.8°, θ_min = 3.5°
ω scans	h = −17→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −27→27
T_min = 0.957, T_max = 0.974	l = −29→29
25253 measured reflections

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) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.063P)² + 1.1529P] where P = (F_o² + 2F_c²)/3
7296 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₁₄N₂	V = 2848.13 (14) Å³
M_r = 270.32	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 10.1878 (3) Å	µ = 0.08 mm⁻¹
b = 16.6399 (4) Å	T = 123 K
c = 17.4959 (5) Å	0.60 × 0.40 × 0.35 mm
β = 106.205 (3)°

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	7296 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	5803 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.974	R_int = 0.028
25253 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	Δρ_max = 0.52 e Å⁻³
7296 reflections	Δρ_min = −0.25 e Å⁻³
190 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 > 2σ(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
N1	−0.02193 (7)	0.41603 (4)	0.11513 (4)	0.0171 (2)
N3	−0.10490 (7)	0.53588 (4)	0.13995 (4)	0.0203 (2)
C2	0.00172 (8)	0.49743 (5)	0.12929 (4)	0.0175 (2)
C4	−0.33775 (9)	0.48436 (6)	0.13998 (5)	0.0236 (2)
C5	−0.41655 (9)	0.41533 (6)	0.13157 (6)	0.0246 (2)
C6	−0.36456 (9)	0.34053 (6)	0.11689 (5)	0.0230 (2)
C7	−0.23322 (9)	0.33246 (5)	0.10945 (5)	0.0204 (2)
C8	−0.15513 (8)	0.40216 (5)	0.11787 (4)	0.0175 (2)
C9	−0.20463 (8)	0.47749 (5)	0.13339 (5)	0.0189 (2)
C11	0.07472 (8)	0.35411 (5)	0.11440 (4)	0.0170 (2)
C12	0.04519 (9)	0.29794 (5)	0.05292 (5)	0.0219 (2)
C13	0.13562 (10)	0.23476 (5)	0.05505 (6)	0.0249 (2)
C14	0.25548 (10)	0.22842 (5)	0.11667 (6)	0.0249 (2)
C15	0.28460 (9)	0.28592 (6)	0.17671 (5)	0.0244 (2)
C16	0.19401 (9)	0.34852 (5)	0.17652 (5)	0.0207 (2)
C21	0.13044 (8)	0.53770 (5)	0.12998 (5)	0.0180 (2)
C22	0.20146 (9)	0.51883 (5)	0.07441 (5)	0.0206 (2)
C23	0.32060 (9)	0.56028 (6)	0.07548 (5)	0.0235 (2)
C24	0.36977 (9)	0.61969 (6)	0.13203 (6)	0.0253 (2)
C25	0.29922 (10)	0.63848 (5)	0.18729 (6)	0.0254 (2)
C26	0.17964 (9)	0.59817 (5)	0.18609 (5)	0.0217 (2)
H4	−0.37244	0.53382	0.14972	0.0283*
H5	−0.50543	0.41859	0.13571	0.0296*
H6	−0.41968	0.29520	0.11203	0.0275*
H7	−0.19908	0.28296	0.09934	0.0245*
H12	−0.03397	0.30262	0.01096	0.0262*
H13	0.11560	0.19638	0.01481	0.0299*
H14	0.31565	0.18613	0.11775	0.0299*
H15	0.36562	0.28249	0.21748	0.0293*
H16	0.21306	0.38614	0.21746	0.0248*
H22	0.16910	0.47870	0.03688	0.0248*
H23	0.36739	0.54820	0.03826	0.0281*
H24	0.44992	0.64692	0.13297	0.0303*
H25	0.33243	0.67821	0.22513	0.0305*
H26	0.13210	0.61136	0.22266	0.0260*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0164 (3)	0.0143 (3)	0.0209 (3)	0.0033 (2)	0.0056 (2)	−0.0001 (2)
N3	0.0191 (3)	0.0166 (3)	0.0259 (3)	0.0036 (2)	0.0075 (2)	−0.0006 (2)
C2	0.0188 (3)	0.0147 (3)	0.0193 (3)	0.0029 (2)	0.0057 (2)	0.0005 (2)
C4	0.0185 (3)	0.0227 (4)	0.0298 (4)	0.0047 (3)	0.0073 (3)	−0.0014 (3)
C5	0.0175 (3)	0.0274 (4)	0.0289 (4)	0.0022 (3)	0.0063 (3)	0.0002 (3)
C6	0.0199 (3)	0.0235 (4)	0.0242 (3)	−0.0013 (3)	0.0041 (3)	0.0005 (3)
C7	0.0207 (3)	0.0175 (3)	0.0224 (3)	0.0011 (3)	0.0049 (3)	−0.0001 (3)
C8	0.0168 (3)	0.0169 (3)	0.0185 (3)	0.0031 (2)	0.0043 (2)	0.0006 (2)
C9	0.0177 (3)	0.0171 (3)	0.0220 (3)	0.0035 (2)	0.0055 (2)	−0.0002 (2)
C11	0.0183 (3)	0.0143 (3)	0.0194 (3)	0.0039 (2)	0.0069 (2)	0.0012 (2)
C12	0.0214 (3)	0.0205 (3)	0.0236 (3)	0.0028 (3)	0.0062 (3)	−0.0045 (3)
C13	0.0275 (4)	0.0197 (4)	0.0304 (4)	0.0034 (3)	0.0130 (3)	−0.0051 (3)
C14	0.0271 (4)	0.0198 (3)	0.0319 (4)	0.0088 (3)	0.0148 (3)	0.0038 (3)
C15	0.0227 (4)	0.0248 (4)	0.0256 (4)	0.0095 (3)	0.0064 (3)	0.0054 (3)
C16	0.0222 (3)	0.0197 (3)	0.0196 (3)	0.0058 (3)	0.0049 (3)	0.0012 (3)
C21	0.0190 (3)	0.0157 (3)	0.0200 (3)	0.0033 (2)	0.0066 (2)	0.0029 (2)
C22	0.0212 (3)	0.0214 (3)	0.0199 (3)	0.0043 (3)	0.0068 (3)	0.0020 (3)
C23	0.0226 (4)	0.0250 (4)	0.0253 (4)	0.0058 (3)	0.0107 (3)	0.0063 (3)
C24	0.0225 (4)	0.0217 (4)	0.0335 (4)	0.0009 (3)	0.0109 (3)	0.0060 (3)
C25	0.0275 (4)	0.0181 (3)	0.0322 (4)	−0.0028 (3)	0.0109 (3)	−0.0008 (3)
C26	0.0253 (4)	0.0166 (3)	0.0255 (3)	−0.0001 (3)	0.0109 (3)	−0.0007 (3)

Geometric parameters (Å, º) top

N1—C2	1.3859 (11)	C21—C26	1.3974 (12)
N1—C8	1.3905 (11)	C22—C23	1.3916 (13)
N1—C11	1.4277 (11)	C23—C24	1.3894 (14)
N3—C2	1.3180 (11)	C24—C25	1.3918 (14)
N3—C9	1.3872 (11)	C25—C26	1.3857 (14)
C2—C21	1.4697 (12)	C4—H4	0.9300
C4—C5	1.3855 (14)	C5—H5	0.9300
C4—C9	1.3975 (13)	C6—H6	0.9300
C5—C6	1.4042 (14)	C7—H7	0.9300
C6—C7	1.3866 (13)	C12—H12	0.9300
C7—C8	1.3908 (12)	C13—H13	0.9300
C8—C9	1.4056 (12)	C14—H14	0.9300
C11—C12	1.3930 (11)	C15—H15	0.9300
C11—C16	1.3891 (12)	C16—H16	0.9300
C12—C13	1.3915 (13)	C22—H22	0.9300
C13—C14	1.3892 (15)	C23—H23	0.9300
C14—C15	1.3903 (13)	C24—H24	0.9300
C15—C16	1.3911 (13)	C25—H25	0.9300
C21—C22	1.4000 (12)	C26—H26	0.9300

C2—N1—C8	106.18 (7)	C24—C25—C26	120.20 (9)
C2—N1—C11	128.39 (7)	C21—C26—C25	120.04 (8)
C8—N1—C11	124.24 (7)	C5—C4—H4	121.00
C2—N3—C9	105.18 (7)	C9—C4—H4	121.00
N1—C2—N3	113.00 (7)	C4—C5—H5	119.00
N1—C2—C21	123.87 (7)	C6—C5—H5	119.00
N3—C2—C21	123.11 (7)	C5—C6—H6	119.00
C5—C4—C9	118.06 (9)	C7—C6—H6	119.00
C4—C5—C6	121.16 (9)	C6—C7—H7	122.00
C5—C6—C7	121.75 (9)	C8—C7—H7	122.00
C6—C7—C8	116.60 (8)	C11—C12—H12	120.00
N1—C8—C7	132.04 (8)	C13—C12—H12	120.00
N1—C8—C9	105.36 (7)	C12—C13—H13	120.00
C7—C8—C9	122.59 (8)	C14—C13—H13	120.00
N3—C9—C4	129.88 (8)	C13—C14—H14	120.00
N3—C9—C8	110.28 (7)	C15—C14—H14	120.00
C4—C9—C8	119.85 (8)	C14—C15—H15	120.00
N1—C11—C12	119.36 (7)	C16—C15—H15	120.00
N1—C11—C16	119.76 (7)	C11—C16—H16	120.00
C12—C11—C16	120.83 (8)	C15—C16—H16	120.00
C11—C12—C13	119.18 (8)	C21—C22—H22	120.00
C12—C13—C14	120.68 (8)	C23—C22—H22	120.00
C13—C14—C15	119.35 (9)	C22—C23—H23	120.00
C14—C15—C16	120.80 (8)	C24—C23—H23	120.00
C11—C16—C15	119.14 (8)	C23—C24—H24	120.00
C2—C21—C22	121.66 (7)	C25—C24—H24	120.00
C2—C21—C26	118.58 (8)	C24—C25—H25	120.00
C22—C21—C26	119.72 (8)	C26—C25—H25	120.00
C21—C22—C23	119.83 (8)	C21—C26—H26	120.00
C22—C23—C24	120.13 (8)	C25—C26—H26	120.00
C23—C24—C25	120.07 (9)

C8—N1—C2—N3	−0.56 (8)	C5—C6—C7—C8	0.47 (13)
C8—N1—C2—C21	−178.75 (7)	C6—C7—C8—N1	179.10 (8)
C11—N1—C2—N3	−168.36 (7)	C6—C7—C8—C9	0.20 (12)
C11—N1—C2—C21	13.45 (12)	N1—C8—C9—N3	0.02 (8)
C2—N1—C8—C7	−178.75 (8)	N1—C8—C9—C4	−179.91 (7)
C2—N1—C8—C9	0.30 (8)	C7—C8—C9—N3	179.18 (7)
C11—N1—C8—C7	−10.30 (13)	C7—C8—C9—C4	−0.76 (12)
C11—N1—C8—C9	168.74 (7)	N1—C11—C12—C13	−175.99 (8)
C2—N1—C11—C12	−134.48 (8)	C16—C11—C12—C13	1.25 (13)
C2—N1—C11—C16	48.25 (11)	N1—C11—C16—C15	177.36 (8)
C8—N1—C11—C12	59.73 (10)	C12—C11—C16—C15	0.14 (13)
C8—N1—C11—C16	−117.54 (9)	C11—C12—C13—C14	−1.38 (14)
C9—N3—C2—N1	0.56 (9)	C12—C13—C14—C15	0.13 (15)
C9—N3—C2—C21	178.77 (7)	C13—C14—C15—C16	1.29 (14)
C2—N3—C9—C4	179.58 (9)	C14—C15—C16—C11	−1.42 (14)
C2—N3—C9—C8	−0.35 (9)	C2—C21—C22—C23	177.85 (8)
N1—C2—C21—C22	40.41 (12)	C26—C21—C22—C23	0.10 (12)
N1—C2—C21—C26	−141.81 (8)	C2—C21—C26—C25	−178.67 (8)
N3—C2—C21—C22	−137.60 (8)	C22—C21—C26—C25	−0.85 (13)
N3—C2—C21—C26	40.18 (11)	C21—C22—C23—C24	0.64 (14)
C9—C4—C5—C6	0.03 (14)	C22—C23—C24—C25	−0.65 (14)
C5—C4—C9—N3	−179.31 (9)	C23—C24—C25—C26	−0.11 (14)
C5—C4—C9—C8	0.62 (12)	C24—C25—C26—C21	0.86 (14)
C4—C5—C6—C7	−0.60 (14)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4–C9 fused benzene ring and Cg1 is the centroid of the N1/C2/N3/C9/C8 imidazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N3ⁱ	0.93	2.62	3.4829 (11)	154
C16—H16···Cg2ⁱⁱ	0.93	2.68	3.4843 (9)	146
C22—H22···Cg1ⁱⁱⁱ	0.93	2.91	3.3966 (9)	114
C23—H23···Cg2ⁱⁱⁱ	0.93	2.83	3.4609 (9)	126

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄N₂
M_r	270.32
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	10.1878 (3), 16.6399 (4), 17.4959 (5)
β (°)	106.205 (3)
V (Å³)	2848.13 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.60 × 0.40 × 0.35

Data collection
Diffractometer	Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.957, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	25253, 7296, 5803
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.862

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.137, 1.06
No. of reflections	7296
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.25

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4–C9 fused benzene ring and Cg1 is the centroid of the N1/C2/N3/C9/C8 imidazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N3ⁱ	0.93	2.62	3.4829 (11)	154
C16—H16···Cg2ⁱⁱ	0.93	2.68	3.4843 (9)	146
C22—H22···Cg1ⁱⁱⁱ	0.93	2.91	3.3966 (9)	114
C23—H23···Cg2ⁱⁱⁱ	0.93	2.83	3.4609 (9)	126

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

Acknowledgements

KJ thanks the DST (No. SR/S1/IC-73/2010) for a fellowship. JJ thanks the DST (No. SR/S1/IC-73/2010), the UGC [F. No. 36–21/2008 (SR)] and the DRDO (NRB-213/MAT/10–11) for providing funds for this research study. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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Volume 68| Part 12| December 2012| Page o3283

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