1,2-Diphenyl-1H-benzimidazole.

In the title mol-ecule, 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 inter-actions 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 = 270.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.137

S = 1.06

7296 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.25 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044960/hg5265sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044960/hg5265Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044960/hg5265Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H14N2	F(000) = 1136
Mr = 270.32	Dx = 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

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

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(Fo2) + (0.063P)2 + 1.1529P] where P = (Fo2 + 2Fc2)/3
7296 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .