4,4'-Bis(benzimidazol-1-yl)biphen-yl.

The mol-ecule of the title compound, C(26)H(18)N(4), resides on a crystallographic inversion centre with a dihedral angle of 44.94 (5)° between the benzimidazole ring system and the benzene ring. The primary hydrogen bond is C-H⋯N and inversion-related pairs of these generate a chain of rings along the c-axis direction; π⋯π stacking involving the benzimidazole groups with inter-planar separations of ca 3.4 Å complete the inter-actions.

Related literature

For related literature, see: Bu et al. (2007 ▶); Buchwald et al. (2001 ▶); Cristau et al. (2004 ▶); Su et al. (2003 ▶).

Experimental

Crystal data

C26H18N4

M = 386.44

Monoclinic,

a = 19.628 (4) Å

b = 6.8964 (14) Å

c = 13.760 (3) Å

β = 90.74 (3)°

V = 1862.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.26 × 0.22 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.904, T max = 1.000 (expected range = 0.897–0.992)

9091 measured reflections

1644 independent reflections

1415 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.10

1644 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063350/gg2046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063350/gg2046Isup2.hkl

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

C26H18N4	F000 = 808
Mr = 386.44	Dx = 1.378 Mg m−3
Monoclinic, C2/c	Melting point: 566 K
Hall symbol: -c 2yc	Mo Kα radiation λ = 0.71073 Å
a = 19.628 (4) Å	Cell parameters from 2932 reflections
b = 6.8964 (14) Å	θ = 2.6–28.7º
c = 13.760 (3) Å	µ = 0.08 mm−1
β = 90.74 (3)º	T = 293 (2) K
V = 1862.4 (7) Å3	Block, colorless
Z = 4	0.26 × 0.22 × 0.10 mm

Bruker SMART 1000 CCD diffractometer	1644 independent reflections
Radiation source: fine-focus sealed tube	1415 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
Detector resolution: 9 pixels mm-1	θmax = 25.0º
T = 293(2) K	θmin = 3.0º
ω scans	h = −23→23
Absorption correction: multi-scan(SADABS; Bruker, 1998)	k = −8→8
Tmin = 0.904, Tmax = 1.000	l = −16→16
9091 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0718P)2 + 0.0391P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103	(Δ/σ)max = 0.001
S = 1.10	Δρmax = 0.18 e Å−3
1644 reflections	Δρmin = −0.17 e Å−3
137 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (4)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
N1	0.22326 (5)	0.98108 (14)	0.82891 (7)	0.0259 (3)
N2	0.28767 (5)	0.99037 (13)	0.69471 (7)	0.0196 (3)
C1	0.28458 (6)	0.99959 (16)	0.79430 (8)	0.0233 (3)
H1	0.3229	1.0175	0.8337	0.028*
C2	0.18197 (6)	0.95587 (16)	0.74690 (8)	0.0217 (3)
C3	0.11196 (6)	0.91962 (17)	0.74020 (9)	0.0271 (3)
H3	0.0854	0.9134	0.7956	0.033*
C4	0.08336 (6)	0.89337 (17)	0.64895 (9)	0.0289 (4)
H4	0.0369	0.8694	0.6429	0.035*
C5	0.12330 (6)	0.90221 (16)	0.56532 (9)	0.0269 (3)
H5	0.1025	0.8845	0.5049	0.032*
C6	0.19250 (6)	0.93632 (16)	0.56982 (8)	0.0221 (3)
H6	0.2189	0.9410	0.5142	0.027*
C7	0.22077 (6)	0.96335 (15)	0.66211 (9)	0.0197 (3)
C8	0.34804 (6)	0.99569 (15)	0.63884 (8)	0.0191 (3)
C9	0.35123 (6)	1.10302 (16)	0.55419 (8)	0.0239 (3)
H9	0.3136	1.1741	0.5331	0.029*
C10	0.41052 (6)	1.10460 (16)	0.50080 (9)	0.0234 (3)
H10	0.4118	1.1770	0.4438	0.028*
C11	0.46851 (6)	1.00092 (15)	0.52969 (8)	0.0195 (3)
C12	0.46409 (6)	0.89818 (18)	0.61685 (8)	0.0268 (3)
H12	0.5021	0.8305	0.6396	0.032*
C13	0.40515 (6)	0.89417 (18)	0.67017 (8)	0.0256 (3)
H13	0.4037	0.8229	0.7275	0.031*

	U11	U22	U33	U12	U13	U23
N1	0.0289 (6)	0.0284 (6)	0.0204 (6)	−0.0051 (4)	0.0060 (5)	−0.0016 (4)
N2	0.0212 (6)	0.0207 (5)	0.0170 (6)	−0.0025 (4)	0.0038 (4)	−0.0006 (4)
C1	0.0271 (7)	0.0255 (6)	0.0172 (7)	−0.0033 (5)	0.0019 (5)	−0.0006 (5)
C2	0.0255 (6)	0.0185 (6)	0.0211 (7)	−0.0009 (5)	0.0058 (5)	−0.0011 (5)
C3	0.0249 (7)	0.0249 (7)	0.0318 (8)	−0.0006 (5)	0.0103 (5)	−0.0007 (5)
C4	0.0213 (6)	0.0244 (7)	0.0409 (8)	−0.0001 (5)	0.0012 (6)	0.0000 (5)
C5	0.0279 (7)	0.0235 (7)	0.0292 (7)	0.0013 (5)	−0.0044 (5)	−0.0002 (5)
C6	0.0267 (6)	0.0191 (6)	0.0206 (7)	0.0014 (5)	0.0015 (5)	0.0008 (5)
C7	0.0212 (6)	0.0155 (6)	0.0226 (7)	−0.0004 (4)	0.0025 (5)	0.0011 (4)
C8	0.0203 (6)	0.0191 (6)	0.0178 (6)	−0.0045 (4)	0.0034 (5)	−0.0033 (4)
C9	0.0256 (6)	0.0217 (7)	0.0245 (7)	0.0049 (5)	0.0046 (5)	0.0031 (5)
C10	0.0298 (7)	0.0203 (6)	0.0203 (6)	0.0009 (5)	0.0059 (5)	0.0037 (5)
C11	0.0196 (7)	0.0204 (6)	0.0185 (7)	−0.0070 (4)	0.0003 (5)	−0.0025 (4)
C12	0.0166 (6)	0.0412 (8)	0.0227 (7)	−0.0021 (5)	−0.0016 (5)	0.0071 (5)
C13	0.0218 (6)	0.0369 (7)	0.0181 (7)	−0.0055 (5)	−0.0012 (5)	0.0078 (5)

C9—C8	1.3822 (16)	C5—C6	1.3790 (17)
C9—C10	1.3842 (16)	C5—C4	1.4021 (18)
C9—H9	0.9300	C5—H5	0.9300
N2—C1	1.3740 (15)	C4—C3	1.3806 (18)
N2—C7	1.3945 (15)	C4—H4	0.9300
N2—C8	1.4212 (15)	C13—C12	1.3781 (16)
C10—C11	1.3974 (17)	C13—C8	1.3856 (17)
C10—H10	0.9300	C13—H13	0.9300
N1—C1	1.3063 (16)	C12—H12	0.9300
N1—C2	1.3916 (16)	C2—C3	1.3986 (17)
C11—C12	1.3967 (17)	C3—H3	0.9300
C11—C11i	1.491 (2)	C6—H6	0.9300
C7—C6	1.3918 (17)	C1—H1	0.9300
C7—C2	1.4024 (17)
C8—C9—C10	119.93 (11)	C12—C13—C8	120.37 (11)
C8—C9—H9	120.0	C12—C13—H13	119.8
C10—C9—H9	120.0	C8—C13—H13	119.8
C1—N2—C7	105.87 (10)	C13—C12—C11	121.94 (11)
C1—N2—C8	125.89 (11)	C13—C12—H12	119.0
C7—N2—C8	128.14 (10)	C11—C12—H12	119.0
C9—C10—C11	122.16 (11)	N1—C2—C3	129.57 (11)
C9—C10—H10	118.9	N1—C2—C7	110.69 (10)
C11—C10—H10	118.9	C3—C2—C7	119.70 (11)
C1—N1—C2	104.25 (10)	C4—C3—C2	118.10 (12)
C12—C11—C10	116.39 (11)	C4—C3—H3	120.9
C12—C11—C11i	121.83 (13)	C2—C3—H3	120.9
C10—C11—C11i	121.78 (13)	C9—C8—C13	119.18 (11)
C6—C7—N2	132.38 (11)	C9—C8—N2	121.11 (10)
C6—C7—C2	122.66 (11)	C13—C8—N2	119.70 (11)
N2—C7—C2	104.86 (10)	C5—C6—C7	116.40 (11)
C6—C5—C4	122.10 (12)	C5—C6—H6	121.8
C6—C5—H5	118.9	C7—C6—H6	121.8
C4—C5—H5	118.9	N1—C1—N2	114.33 (12)
C3—C4—C5	121.03 (11)	N1—C1—H1	122.8
C3—C4—H4	119.5	N2—C1—H1	122.8
C5—C4—H4	119.5
C8—C9—C10—C11	−0.30 (18)	C5—C4—C3—C2	0.17 (17)
C9—C10—C11—C12	−1.33 (17)	N1—C2—C3—C4	−177.73 (11)
C9—C10—C11—C11i	178.27 (12)	C7—C2—C3—C4	−0.38 (16)
C1—N2—C7—C6	−177.15 (12)	C10—C9—C8—C13	1.41 (16)
C8—N2—C7—C6	−0.74 (18)	C10—C9—C8—N2	−179.55 (10)
C1—N2—C7—C2	−0.74 (11)	C12—C13—C8—C9	−0.85 (17)
C8—N2—C7—C2	175.68 (10)	C12—C13—C8—N2	−179.90 (10)
C6—C5—C4—C3	0.30 (18)	C1—N2—C8—C9	−138.05 (12)
C8—C13—C12—C11	−0.85 (18)	C7—N2—C8—C9	46.20 (15)
C10—C11—C12—C13	1.90 (17)	C1—N2—C8—C13	40.98 (16)
C11i—C11—C12—C13	−177.70 (12)	C7—N2—C8—C13	−134.76 (12)
C1—N1—C2—C3	176.54 (12)	C4—C5—C6—C7	−0.53 (17)
C1—N1—C2—C7	−1.00 (12)	N2—C7—C6—C5	176.21 (11)
C6—C7—C2—N1	177.95 (10)	C2—C7—C6—C5	0.32 (16)
N2—C7—C2—N1	1.09 (12)	C2—N1—C1—N2	0.52 (13)
C6—C7—C2—C3	0.13 (17)	C7—N2—C1—N1	0.14 (13)
N2—C7—C2—C3	−176.73 (10)	C8—N2—C1—N1	−176.38 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1ii	0.93	2.61	3.425 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N1i	0.93	2.61	3.425 (2)	147

Symmetry code: (i) .