2-(Naphthalen-1-yl)-1-phenyl-1H-benzimid-azole benzene hemisolvate.

In the title compound, C23H16N2·0.5C6H6, the benzimidazole unit [maximum deviation = 0.0258 (6) Å] and the naphthalene ring system [maximum deviation = 0.0254 (6) Å] are both essentially planar and make a dihedral angle of 61.955 (17)°. The imidazole ring makes dihedral angle of 61.73 (4)° with the phenyl ring. An intra-molecular C-H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, seven weak C-H⋯π inter-actions involving the fused ring system, the benzene solvent mol-ecule, the imidazole phenyl rings are observed, leading to a three-dimensional architecture.

Related literature

For linear and non-linear optical properties and the thermal stability of benzimidazole-based chromophores, see: Cross et al. (1995 ▶). For imidazole as a component of vitamin B12, purine and caffeine, see: Brown (2005 ▶). For commercial and therapeutic applications of substituted benzimidazole derivatives, see: Spasov et al. (1999 ▶). For related crystal structures, see: Jayamoorthy et al. (2012 ▶, 2013 ▶); Rosepriya et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H16N2·0.5C6H6

M = 359.43

Triclinic,

a = 8.5529 (3) Å

b = 9.4517 (3) Å

c = 11.8936 (3) Å

α = 86.334 (2)°

β = 89.838 (2)°

γ = 75.051 (3)°

V = 926.94 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 123 K

0.72 × 0.59 × 0.42 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), using a multifaceted crystal model (Clark & Reid, 1995 ▶)] T min = 0.963, T max = 0.977

57784 measured reflections

12045 independent reflections

9086 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.160

S = 1.05

12045 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681303331X/jj2179sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681303331X/jj2179Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681303331X/jj2179Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681303331X/jj2179Isup4.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C23H16N2·0.5C6H6	Z = 2
Mr = 359.43	F(000) = 378
Triclinic, P1	Dx = 1.288 Mg m−3
Hall symbol: -P 1	Melting point: 392 K
a = 8.5529 (3) Å	Mo Kα radiation, λ = 0.71069 Å
b = 9.4517 (3) Å	Cell parameters from 15125 reflections
c = 11.8936 (3) Å	θ = 3.0–41.0°
α = 86.334 (2)°	µ = 0.08 mm−1
β = 89.838 (2)°	T = 123 K
γ = 75.051 (3)°	Prism, colourless
V = 926.94 (5) Å3	0.72 × 0.59 × 0.42 mm

Agilent Xcalibur Ruby Gemini diffractometer	12045 independent reflections
Radiation source: Enhance (Mo) X-ray Source	9086 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 10.5081 pixels mm-1	θmax = 41.1°, θmin = 3.0°
ω scans	h = −15→15
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), using a multifaceted crystal model (Clark & Reid, 1995)]	k = −17→17
Tmin = 0.963, Tmax = 0.977	l = −21→21
57784 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.076P)2 + 0.0921P] where P = (Fo2 + 2Fc2)/3
12045 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.42 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

	x	y	z	Uiso*/Ueq
N1	0.67234 (7)	0.54147 (6)	0.17737 (5)	0.0196 (1)
N3	0.58580 (7)	0.34162 (7)	0.23145 (5)	0.0218 (1)
C2	0.54214 (8)	0.48307 (7)	0.20135 (6)	0.0197 (1)
C4	0.86569 (9)	0.16857 (8)	0.25577 (6)	0.0230 (2)
C5	1.02936 (9)	0.16196 (8)	0.24850 (6)	0.0241 (2)
C6	1.08319 (9)	0.28681 (9)	0.21552 (6)	0.0237 (2)
C7	0.97488 (9)	0.42165 (8)	0.18733 (6)	0.0222 (2)
C8	0.81081 (8)	0.42675 (7)	0.19437 (6)	0.0194 (1)
C9	0.75441 (8)	0.30379 (7)	0.22843 (6)	0.0200 (2)
C11	0.66581 (8)	0.69261 (7)	0.15057 (5)	0.0190 (1)
C12	0.72504 (9)	0.73392 (8)	0.04813 (6)	0.0217 (2)
C13	0.71614 (9)	0.88153 (8)	0.02178 (6)	0.0247 (2)
C14	0.64697 (9)	0.98608 (8)	0.09676 (7)	0.0253 (2)
C15	0.58828 (9)	0.94403 (8)	0.19913 (7)	0.0259 (2)
C16	0.59863 (9)	0.79665 (8)	0.22698 (6)	0.0233 (2)
C21	0.37491 (8)	0.57825 (7)	0.19356 (6)	0.0194 (2)
C22	0.31678 (9)	0.65122 (8)	0.09166 (6)	0.0230 (2)
C23	0.16256 (9)	0.75196 (9)	0.08347 (6)	0.0252 (2)
C24	0.07012 (9)	0.78075 (8)	0.17773 (7)	0.0243 (2)
C25	0.02654 (9)	0.73198 (9)	0.38062 (7)	0.0270 (2)
C26	0.07884 (10)	0.65771 (10)	0.48214 (7)	0.0291 (2)
C27	0.23194 (10)	0.55553 (10)	0.49096 (6)	0.0271 (2)
C28	0.32981 (9)	0.52890 (8)	0.39875 (6)	0.0225 (2)
C29	0.27828 (8)	0.60281 (7)	0.29210 (5)	0.0187 (2)
C30	0.12426 (8)	0.70669 (8)	0.28362 (6)	0.0210 (2)
C1A	0.55334 (12)	0.12597 (10)	0.47928 (7)	0.0319 (2)
C2A	0.39180 (12)	0.13022 (10)	0.46027 (8)	0.0329 (2)
C3A	0.66115 (11)	−0.00416 (11)	0.51904 (7)	0.0315 (2)
H4	0.83010	0.08400	0.27860	0.0276*
H5	1.10668	0.07119	0.26616	0.0289*
H6	1.19612	0.27882	0.21245	0.0285*
H7	1.01084	0.50599	0.16443	0.0266*
H12	0.77109	0.66228	−0.00334	0.0261*
H13	0.75746	0.91078	−0.04763	0.0297*
H14	0.63978	1.08678	0.07795	0.0303*
H15	0.54107	1.01593	0.25013	0.0311*
H16	0.56028	0.76719	0.29741	0.0279*
H22	0.38129	0.63341	0.02635	0.0276*
H23	0.12295	0.79973	0.01263	0.0302*
H24	−0.03168	0.85133	0.17208	0.0292*
H25	−0.07625	0.80110	0.37523	0.0323*
H26	0.01210	0.67503	0.54642	0.0350*
H27	0.26770	0.50460	0.56147	0.0325*
H28	0.43288	0.46046	0.40632	0.0270*
H1A	0.58997	0.21206	0.46507	0.0383*
H2A	0.31790	0.21918	0.43320	0.0394*
H3A	0.77144	−0.00685	0.53211	0.0378*

	U11	U22	U33	U12	U13	U23
N1	0.0184 (2)	0.0182 (2)	0.0204 (2)	−0.0019 (2)	0.0024 (2)	0.0005 (2)
N3	0.0201 (2)	0.0205 (2)	0.0231 (3)	−0.0031 (2)	0.0015 (2)	0.0016 (2)
C2	0.0188 (2)	0.0205 (3)	0.0184 (2)	−0.0031 (2)	0.0016 (2)	0.0005 (2)
C4	0.0238 (3)	0.0194 (3)	0.0233 (3)	−0.0013 (2)	0.0001 (2)	0.0004 (2)
C5	0.0226 (3)	0.0222 (3)	0.0236 (3)	0.0011 (2)	−0.0003 (2)	−0.0009 (2)
C6	0.0192 (3)	0.0260 (3)	0.0234 (3)	−0.0009 (2)	0.0011 (2)	−0.0025 (2)
C7	0.0197 (3)	0.0226 (3)	0.0230 (3)	−0.0034 (2)	0.0023 (2)	−0.0016 (2)
C8	0.0183 (2)	0.0191 (3)	0.0186 (2)	−0.0013 (2)	0.0016 (2)	−0.0009 (2)
C9	0.0199 (3)	0.0192 (3)	0.0190 (3)	−0.0021 (2)	0.0011 (2)	−0.0003 (2)
C11	0.0184 (2)	0.0184 (2)	0.0186 (2)	−0.0021 (2)	0.0010 (2)	0.0001 (2)
C12	0.0222 (3)	0.0213 (3)	0.0198 (3)	−0.0026 (2)	0.0024 (2)	0.0003 (2)
C13	0.0248 (3)	0.0240 (3)	0.0238 (3)	−0.0050 (2)	−0.0014 (2)	0.0050 (2)
C14	0.0230 (3)	0.0195 (3)	0.0315 (3)	−0.0032 (2)	−0.0053 (3)	0.0023 (2)
C15	0.0245 (3)	0.0214 (3)	0.0303 (3)	−0.0021 (2)	0.0003 (3)	−0.0062 (2)
C16	0.0242 (3)	0.0235 (3)	0.0215 (3)	−0.0045 (2)	0.0034 (2)	−0.0040 (2)
C21	0.0175 (2)	0.0196 (3)	0.0198 (3)	−0.0028 (2)	0.0003 (2)	0.0004 (2)
C22	0.0221 (3)	0.0252 (3)	0.0199 (3)	−0.0036 (2)	−0.0003 (2)	0.0019 (2)
C23	0.0241 (3)	0.0251 (3)	0.0238 (3)	−0.0032 (2)	−0.0043 (2)	0.0041 (2)
C24	0.0201 (3)	0.0219 (3)	0.0282 (3)	−0.0008 (2)	−0.0039 (2)	0.0000 (2)
C25	0.0202 (3)	0.0296 (3)	0.0287 (3)	−0.0011 (3)	0.0032 (2)	−0.0065 (3)
C26	0.0264 (3)	0.0355 (4)	0.0246 (3)	−0.0055 (3)	0.0067 (3)	−0.0059 (3)
C27	0.0273 (3)	0.0326 (4)	0.0199 (3)	−0.0054 (3)	0.0027 (2)	0.0001 (3)
C28	0.0211 (3)	0.0245 (3)	0.0201 (3)	−0.0030 (2)	0.0004 (2)	0.0004 (2)
C29	0.0167 (2)	0.0191 (3)	0.0194 (3)	−0.0033 (2)	−0.0001 (2)	−0.0008 (2)
C30	0.0179 (2)	0.0206 (3)	0.0233 (3)	−0.0023 (2)	−0.0004 (2)	−0.0027 (2)
C1A	0.0385 (4)	0.0284 (4)	0.0274 (3)	−0.0071 (3)	0.0019 (3)	0.0013 (3)
C2A	0.0360 (4)	0.0282 (4)	0.0290 (4)	0.0004 (3)	0.0000 (3)	0.0030 (3)
C3A	0.0301 (4)	0.0350 (4)	0.0271 (3)	−0.0047 (3)	0.0005 (3)	−0.0001 (3)

N1—C2	1.3861 (9)	C27—C28	1.3741 (11)
N1—C8	1.3892 (9)	C28—C29	1.4221 (9)
N1—C11	1.4304 (8)	C29—C30	1.4249 (10)
N3—C2	1.3180 (9)	C4—H4	0.9500
N3—C9	1.3943 (9)	C5—H5	0.9500
C2—C21	1.4798 (10)	C6—H6	0.9500
C4—C5	1.3878 (11)	C7—H7	0.9500
C4—C9	1.4022 (10)	C12—H12	0.9500
C5—C6	1.4066 (11)	C13—H13	0.9500
C6—C7	1.3903 (11)	C14—H14	0.9500
C7—C8	1.3941 (11)	C15—H15	0.9500
C8—C9	1.4055 (9)	C16—H16	0.9500
C11—C12	1.3897 (10)	C22—H22	0.9500
C11—C16	1.3939 (10)	C23—H23	0.9500
C12—C13	1.3928 (10)	C24—H24	0.9500
C13—C14	1.3892 (11)	C25—H25	0.9500
C14—C15	1.3892 (12)	C26—H26	0.9500
C15—C16	1.3912 (10)	C27—H27	0.9500
C21—C22	1.3825 (10)	C28—H28	0.9500
C21—C29	1.4286 (9)	C1A—C2A	1.3906 (15)
C22—C23	1.4131 (11)	C1A—C3A	1.3891 (14)
C23—C24	1.3708 (11)	C2A—C3Ai	1.3876 (14)
C24—C30	1.4191 (11)	C1A—H1A	0.9500
C25—C26	1.3724 (12)	C2A—H2A	0.9500
C25—C30	1.4189 (11)	C3A—H3A	0.9500
C26—C27	1.4120 (13)
C2—N1—C8	106.49 (5)	C5—C4—H4	121.00
C2—N1—C11	126.57 (6)	C9—C4—H4	121.00
C8—N1—C11	126.72 (6)	C4—C5—H5	119.00
C2—N3—C9	104.76 (6)	C6—C5—H5	119.00
N1—C2—N3	113.12 (6)	C5—C6—H6	119.00
N1—C2—C21	120.27 (6)	C7—C6—H6	119.00
N3—C2—C21	126.61 (6)	C6—C7—H7	122.00
C5—C4—C9	118.02 (7)	C8—C7—H7	122.00
C4—C5—C6	121.39 (7)	C11—C12—H12	120.00
C5—C6—C7	121.50 (7)	C13—C12—H12	120.00
C6—C7—C8	116.58 (7)	C12—C13—H13	120.00
N1—C8—C7	131.99 (6)	C14—C13—H13	120.00
N1—C8—C9	105.10 (6)	C13—C14—H14	120.00
C7—C8—C9	122.85 (6)	C15—C14—H14	120.00
N3—C9—C4	129.80 (6)	C14—C15—H15	120.00
N3—C9—C8	110.53 (6)	C16—C15—H15	120.00
C4—C9—C8	119.65 (7)	C11—C16—H16	120.00
N1—C11—C12	119.52 (6)	C15—C16—H16	120.00
N1—C11—C16	119.59 (6)	C21—C22—H22	120.00
C12—C11—C16	120.89 (6)	C23—C22—H22	120.00
C11—C12—C13	119.26 (7)	C22—C23—H23	120.00
C12—C13—C14	120.16 (7)	C24—C23—H23	120.00
C13—C14—C15	120.30 (7)	C23—C24—H24	120.00
C14—C15—C16	120.01 (7)	C30—C24—H24	120.00
C11—C16—C15	119.37 (7)	C26—C25—H25	120.00
C2—C21—C22	119.43 (6)	C30—C25—H25	120.00
C2—C21—C29	120.29 (6)	C25—C26—H26	120.00
C22—C21—C29	120.13 (6)	C27—C26—H26	120.00
C21—C22—C23	120.80 (7)	C26—C27—H27	120.00
C22—C23—C24	120.00 (7)	C28—C27—H27	120.00
C23—C24—C30	120.97 (7)	C27—C28—H28	120.00
C26—C25—C30	120.75 (7)	C29—C28—H28	120.00
C25—C26—C27	119.94 (8)	C2A—C1A—C3A	120.00 (9)
C26—C27—C28	120.78 (7)	C1A—C2A—C3Ai	119.81 (9)
C27—C28—C29	120.63 (7)	C1A—C3A—C2Ai	120.19 (9)
C21—C29—C28	122.80 (6)	C2A—C1A—H1A	120.00
C21—C29—C30	118.72 (6)	C3A—C1A—H1A	120.00
C28—C29—C30	118.48 (6)	C1A—C2A—H2A	120.00
C24—C30—C25	121.24 (7)	C3Ai—C2A—H2A	120.00
C24—C30—C29	119.33 (6)	C1A—C3A—H3A	120.00
C25—C30—C29	119.42 (6)	C2Ai—C3A—H3A	120.00
C8—N1—C2—N3	−0.31 (8)	C16—C11—C12—C13	−0.28 (11)
C8—N1—C2—C21	178.80 (6)	N1—C11—C16—C15	−178.15 (7)
C11—N1—C2—N3	−175.10 (6)	C12—C11—C16—C15	1.18 (11)
C11—N1—C2—C21	4.01 (10)	C11—C12—C13—C14	−0.76 (11)
C2—N1—C8—C7	−177.27 (8)	C12—C13—C14—C15	0.90 (12)
C2—N1—C8—C9	−0.10 (7)	C13—C14—C15—C16	0.00 (12)
C11—N1—C8—C7	−2.50 (12)	C14—C15—C16—C11	−1.03 (12)
C11—N1—C8—C9	174.68 (6)	C2—C21—C22—C23	−174.88 (7)
C2—N1—C11—C12	−120.91 (8)	C29—C21—C22—C23	0.72 (11)
C2—N1—C11—C16	58.42 (10)	C2—C21—C29—C28	−5.79 (10)
C8—N1—C11—C12	65.33 (9)	C2—C21—C29—C30	173.63 (6)
C8—N1—C11—C16	−115.34 (8)	C22—C21—C29—C28	178.65 (7)
C9—N3—C2—N1	0.57 (8)	C22—C21—C29—C30	−1.92 (10)
C9—N3—C2—C21	−178.47 (7)	C21—C22—C23—C24	1.44 (12)
C2—N3—C9—C4	177.86 (7)	C22—C23—C24—C30	−2.34 (12)
C2—N3—C9—C8	−0.62 (8)	C23—C24—C30—C25	−177.62 (8)
N1—C2—C21—C22	60.23 (9)	C23—C24—C30—C29	1.09 (11)
N1—C2—C21—C29	−115.36 (7)	C30—C25—C26—C27	0.42 (13)
N3—C2—C21—C22	−120.80 (8)	C26—C25—C30—C24	178.77 (8)
N3—C2—C21—C29	63.62 (10)	C26—C25—C30—C29	0.05 (13)
C9—C4—C5—C6	0.43 (11)	C25—C26—C27—C28	−0.17 (13)
C5—C4—C9—N3	−178.03 (7)	C26—C27—C28—C29	−0.58 (13)
C5—C4—C9—C8	0.34 (10)	C27—C28—C29—C21	−179.54 (7)
C4—C5—C6—C7	−0.89 (11)	C27—C28—C29—C30	1.04 (11)
C5—C6—C7—C8	0.51 (11)	C21—C29—C30—C24	1.04 (10)
C6—C7—C8—N1	177.03 (7)	C21—C29—C30—C25	179.78 (7)
C6—C7—C8—C9	0.28 (11)	C28—C29—C30—C24	−179.51 (7)
N1—C8—C9—N3	0.45 (8)	C28—C29—C30—C25	−0.77 (10)
N1—C8—C9—C4	−178.22 (6)	C3A—C1A—C2A—C3Ai	−0.10 (13)
C7—C8—C9—N3	177.95 (7)	C2A—C1A—C3A—C2Ai	0.10 (14)
C7—C8—C9—C4	−0.71 (11)	C1A—C2A—C3Ai—C1Ai	0.10 (13)
N1—C11—C12—C13	179.04 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···N3	0.95	2.61	3.2113 (10)	121
C7—H7···Cg4ii	0.95	2.75	3.6019 (8)	150
C15—H15···Cg8iii	0.95	2.99	3.6981 (9)	132
C15—H15···Cg8iv	0.95	2.99	3.6981 (9)	132
C22—H22···Cg1v	0.95	2.91	3.6478 (8)	136
C24—H24···Cg3vi	0.95	2.76	3.4888 (9)	134
C26—H26···Cg2iv	0.95	2.87	3.5801 (9)	133
C27—H27···Cg1iv	0.95	2.97	3.7258 (8)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4 and Cg8 are the centroids of the N1/C2/N3/C9/C8 imidazole ring, the C4–C9 fused benzene ring, the C11–C16 phenyl ring, the C21–C24,C30/C29 fused benzene ring and the C1A,C2A,C3A′,C1A′,C2A′,C3A benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯N3	0.95	2.61	3.2113 (10)	121
C7—H7⋯Cg4i	0.95	2.75	3.6019 (8)	150
C15—H15⋯Cg8ii	0.95	2.99	3.6981 (9)	132
C15—H15⋯Cg8iii	0.95	2.99	3.6981 (9)	132
C22—H22⋯Cg1iv	0.95	2.91	3.6478 (8)	136
C24—H24⋯Cg3v	0.95	2.76	3.4888 (9)	134
C26—H26⋯Cg2iii	0.95	2.87	3.5801 (9)	133
C27—H27⋯Cg1iii	0.95	2.97	3.7258 (8)	137

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .