4-[(E)-Phenyl-imino-meth-yl]benzonitrile.

In the mol-ecule of the title compound, C(14)H(10)N(2), the two aromatic rings are oriented at a dihedral angle of 32.22 (6)°. In the crystal structure, inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into centrosymmetric R(2) (2)(10) dimers. A weak π-π inter-action between the cyanobenzene rings, with a centroid-centroid distance of 3.8447 (3) Å, further stabilizes the crystal structure. There is also a C-H⋯π inter-action between the aniline ring and a CH group of the cyanobenzene ring.

Related literature

For related structures, see: Ojala et al. (2002 ▶). For ring motif details, see: Bernstein et al. (1995 ▶); Etter (1990 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10N2

M = 206.24

Monoclinic,

a = 7.2673 (4) Å

b = 10.0287 (7) Å

c = 15.4306 (12) Å

β = 96.177 (2)°

V = 1118.08 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 (2) K

0.20 × 0.15 × 0.12 mm

Data collection

Bruker Kappa-APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.983, T max = 0.994

13128 measured reflections

2883 independent reflections

1423 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.118

S = 1.03

2883 reflections

176 parameters

All H-atom parameters refined

Δρmax = 0.13 e Å−3

Δρmin = −0.10 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008672/hk2445sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008672/hk2445Isup2.hkl

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

C14H10N2	F000 = 432
Mr = 206.24	Dx = 1.226 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2883 reflections
a = 7.2673 (4) Å	θ = 2.4–28.7º
b = 10.0287 (7) Å	µ = 0.07 mm−1
c = 15.4306 (12) Å	T = 296 (2) K
β = 96.177 (2)º	Prismatic, yellow
V = 1118.08 (13) Å3	0.20 × 0.15 × 0.12 mm
Z = 4

Bruker Kappa-APEXII CCD diffractometer	2883 independent reflections
Radiation source: fine-focus sealed tube	1423 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
Detector resolution: 7.30 pixels mm-1	θmax = 28.7º
T = 296(2) K	θmin = 2.4º
ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.983, Tmax = 0.994	l = −20→20
13128 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	All H-atom parameters refined
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0364P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2883 reflections	Δρmax = 0.13 e Å−3
176 parameters	Δρmin = −0.10 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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	0.70615 (14)	0.08086 (11)	0.10666 (8)	0.0518 (3)
N2	0.05182 (19)	0.57458 (14)	−0.13327 (10)	0.0855 (5)
C1	0.57569 (17)	0.23345 (13)	−0.00193 (9)	0.0462 (4)
C2	0.40486 (19)	0.23930 (15)	0.03050 (10)	0.0559 (4)
H2	0.3870 (17)	0.1816 (14)	0.0777 (9)	0.067*
C3	0.27073 (19)	0.32560 (16)	−0.00409 (10)	0.0593 (4)
H3	0.1494 (18)	0.3263 (13)	0.0181 (9)	0.071*
C4	0.30456 (17)	0.40866 (13)	−0.07259 (9)	0.0493 (4)
C5	0.4727 (2)	0.40351 (15)	−0.10663 (10)	0.0538 (4)
H5	0.4929 (16)	0.4628 (13)	−0.1547 (9)	0.065*
C6	0.60682 (19)	0.31589 (15)	−0.07083 (10)	0.0528 (4)
H6	0.7273 (17)	0.3117 (13)	−0.0919 (9)	0.063*
C7	0.72303 (19)	0.14630 (14)	0.03760 (10)	0.0519 (4)
H7	0.8385 (17)	0.1419 (12)	0.0080 (8)	0.062*
C8	0.1639 (2)	0.50057 (16)	−0.10713 (10)	0.0610 (4)
C9	0.85826 (18)	0.00574 (13)	0.14575 (9)	0.0476 (4)
C10	0.8196 (2)	−0.11183 (15)	0.18708 (10)	0.0569 (4)
H10	0.6901 (18)	−0.1361 (13)	0.1860 (9)	0.068*
C11	0.9612 (2)	−0.18768 (16)	0.22793 (10)	0.0657 (5)
H11	0.9274 (18)	−0.2675 (15)	0.2552 (10)	0.079*
C12	1.1415 (2)	−0.14576 (17)	0.22995 (11)	0.0668 (5)
H12	1.2406 (18)	−0.1973 (15)	0.2609 (10)	0.080*
C13	1.1803 (2)	−0.02736 (18)	0.19159 (11)	0.0684 (5)
H13	1.305 (2)	0.0051 (15)	0.1918 (9)	0.082*
C14	1.03990 (19)	0.04859 (16)	0.14922 (11)	0.0605 (4)
H14	1.0655 (18)	0.1354 (14)	0.1248 (9)	0.073*

	U11	U22	U33	U12	U13	U23
N1	0.0550 (7)	0.0462 (7)	0.0531 (8)	0.0004 (5)	0.0010 (6)	0.0009 (6)
N2	0.0759 (9)	0.0934 (11)	0.0861 (11)	0.0287 (9)	0.0031 (8)	0.0113 (9)
C1	0.0490 (8)	0.0449 (8)	0.0445 (9)	0.0007 (6)	0.0040 (7)	−0.0042 (7)
C2	0.0552 (8)	0.0586 (10)	0.0550 (11)	−0.0002 (8)	0.0104 (8)	0.0092 (8)
C3	0.0482 (8)	0.0703 (11)	0.0606 (11)	0.0040 (8)	0.0109 (8)	0.0044 (9)
C4	0.0509 (8)	0.0485 (9)	0.0473 (9)	0.0033 (7)	−0.0005 (7)	−0.0045 (7)
C5	0.0621 (9)	0.0525 (9)	0.0470 (10)	0.0015 (7)	0.0070 (8)	0.0037 (7)
C6	0.0511 (8)	0.0595 (10)	0.0490 (10)	0.0035 (8)	0.0102 (7)	0.0008 (8)
C7	0.0531 (8)	0.0507 (9)	0.0518 (10)	0.0023 (7)	0.0060 (7)	−0.0034 (8)
C8	0.0597 (9)	0.0658 (11)	0.0571 (11)	0.0072 (9)	0.0036 (8)	−0.0016 (9)
C9	0.0559 (8)	0.0414 (8)	0.0447 (9)	0.0025 (7)	0.0024 (7)	−0.0017 (7)
C10	0.0656 (9)	0.0498 (9)	0.0535 (10)	−0.0058 (8)	−0.0024 (8)	0.0003 (8)
C11	0.0921 (12)	0.0461 (10)	0.0556 (11)	−0.0021 (9)	−0.0072 (9)	0.0045 (8)
C12	0.0790 (12)	0.0624 (11)	0.0565 (11)	0.0186 (9)	−0.0047 (9)	0.0014 (9)
C13	0.0580 (9)	0.0749 (12)	0.0718 (12)	0.0052 (9)	0.0051 (9)	0.0107 (10)
C14	0.0570 (9)	0.0559 (9)	0.0682 (12)	0.0006 (8)	0.0046 (8)	0.0136 (9)

N1—C7	1.2686 (17)	C6—H6	0.967 (12)
N1—C9	1.4177 (16)	C7—H7	0.999 (12)
N2—C8	1.1429 (17)	C9—C10	1.3835 (18)
C1—C6	1.3845 (19)	C9—C14	1.3838 (18)
C1—C2	1.3888 (17)	C10—C11	1.376 (2)
C1—C7	1.4635 (18)	C10—H10	0.971 (12)
C2—C3	1.3683 (19)	C11—C12	1.373 (2)
C2—H2	0.950 (14)	C11—H11	0.949 (15)
C3—C4	1.3883 (19)	C12—C13	1.370 (2)
C3—H3	0.979 (13)	C12—H12	0.970 (14)
C4—C5	1.3823 (19)	C13—C14	1.3801 (19)
C4—C8	1.436 (2)	C13—H13	0.965 (14)
C5—C6	1.3823 (19)	C14—H14	0.975 (14)
C5—H5	0.975 (13)
C7—N1—C9	119.40 (12)	C1—C7—H7	116.7 (8)
C6—C1—C2	118.54 (13)	N2—C8—C4	178.87 (17)
C6—C1—C7	120.26 (12)	C10—C9—C14	119.13 (13)
C2—C1—C7	121.16 (13)	C10—C9—N1	117.48 (12)
C3—C2—C1	120.87 (14)	C14—C9—N1	123.25 (13)
C3—C2—H2	122.3 (8)	C11—C10—C9	120.22 (14)
C1—C2—H2	116.8 (8)	C11—C10—H10	123.0 (8)
C2—C3—C4	119.97 (14)	C9—C10—H10	116.8 (8)
C2—C3—H3	119.9 (8)	C12—C11—C10	120.37 (16)
C4—C3—H3	120.1 (8)	C12—C11—H11	122.7 (9)
C5—C4—C3	120.20 (13)	C10—C11—H11	116.9 (9)
C5—C4—C8	120.42 (13)	C13—C12—C11	119.72 (16)
C3—C4—C8	119.37 (13)	C13—C12—H12	119.9 (8)
C6—C5—C4	119.08 (14)	C11—C12—H12	120.3 (8)
C6—C5—H5	122.3 (7)	C12—C13—C14	120.48 (16)
C4—C5—H5	118.6 (7)	C12—C13—H13	121.9 (9)
C5—C6—C1	121.34 (14)	C14—C13—H13	117.6 (9)
C5—C6—H6	121.2 (8)	C13—C14—C9	120.02 (14)
C1—C6—H6	117.5 (8)	C13—C14—H14	121.0 (8)
N1—C7—C1	121.76 (13)	C9—C14—H14	118.9 (8)
N1—C7—H7	121.6 (7)
C6—C1—C2—C3	−0.7 (2)	C2—C1—C7—N1	−5.6 (2)
C7—C1—C2—C3	176.87 (14)	C7—N1—C9—C10	−146.46 (13)
C1—C2—C3—C4	0.1 (2)	C7—N1—C9—C14	37.8 (2)
C2—C3—C4—C5	0.7 (2)	C14—C9—C10—C11	−2.7 (2)
C2—C3—C4—C8	−178.79 (13)	N1—C9—C10—C11	−178.56 (14)
C3—C4—C5—C6	−0.8 (2)	C9—C10—C11—C12	1.6 (2)
C8—C4—C5—C6	178.69 (13)	C10—C11—C12—C13	0.5 (3)
C4—C5—C6—C1	0.1 (2)	C11—C12—C13—C14	−1.5 (3)
C2—C1—C6—C5	0.6 (2)	C12—C13—C14—C9	0.4 (3)
C7—C1—C6—C5	−176.99 (12)	C10—C9—C14—C13	1.6 (2)
C9—N1—C7—C1	−175.33 (11)	N1—C9—C14—C13	177.28 (14)
C6—C1—C7—N1	172.00 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2i	0.980 (13)	2.616 (14)	3.473 (2)	146.1 (10)
C5—H5···Cgii	0.975 (13)	2.650 (14)	3.5970 (17)	163.9 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N2i	0.980 (13)	2.616 (14)	3.473 (2)	146.1 (10)
C5—H5⋯Cgii	0.975 (13)	2.650 (14)	3.5970 (17)	163.9 (11)

Symmetry codes: (i) ; (ii) . Cg is the centroid of atoms C9–C14.