2-(2-Hydroxy-benzyl-ideneamino)benzonitrile.

The mol-ecule of the title compound, C(14)H(10)N(2)O, displays a trans configuration with respect to the C=N double bond. The mol-ecule is roughly planar; the two aromatic rings make a dihedral angle of 9.3 (3)°. Such a planar conformation is induced by the strong intra-molecular O-H⋯N hydrogen bond between the imine and hydroxyl groups.

Related literature

For the structures of similar Schiff base compounds, see: Cheng et al. (2005 ▶, 2006 ▶). For related literature, see: Chen et al. (2008 ▶); Elmah et al. (1999 ▶); May et al. (2004 ▶); Weber et al. (2007 ▶); Xu et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10N2O

M = 222.24

Monoclinic,

a = 4.7667 (10) Å

b = 16.190 (3) Å

c = 7.6714 (15) Å

β = 93.30 (3)°

V = 591.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.20 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.981, T max = 1.00 (expected range = 0.977–0.996)

5470 measured reflections

1201 independent reflections

633 reflections with I > 2σ(I)

R int = 0.105

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.136

S = 1.03

1201 reflections

155 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801163X/dn2331sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801163X/dn2331Isup2.hkl

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

C14H10N2O	F000 = 232
Mr = 222.24	Dx = 1.249 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4123 reflections
a = 4.7667 (10) Å	θ = 3.7–28.7º
b = 16.190 (3) Å	µ = 0.08 mm−1
c = 7.6714 (15) Å	T = 293 (2) K
β = 93.30 (3)º	Block, colorless
V = 591.0 (2) Å3	0.20 × 0.05 × 0.05 mm
Z = 2

Rigaku Mercury2 diffractometer	1201 independent reflections
Radiation source: fine-focus sealed tube	633 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.105
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 3.7º
ω scans	h = −5→5
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −19→19
Tmin = 0.981, Tmax = 1.00	l = −9→9
5470 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)] = 0.061	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1201 reflections	Δρmax = 0.15 e Å−3
155 parameters	Δρmin = −0.18 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	−0.0060 (10)	0.5064 (3)	0.8304 (7)	0.0474 (15)
C2	−0.0982 (11)	0.5462 (4)	0.6745 (9)	0.0580 (16)
C3	−0.2999 (13)	0.6076 (4)	0.6777 (10)	0.076 (2)
H3	−0.3594	0.6343	0.5747	0.091*
C4	−0.4118 (14)	0.6293 (4)	0.8306 (12)	0.0747 (19)
H4	−0.5453	0.6712	0.8303	0.090*
C5	−0.3320 (12)	0.5906 (4)	0.9860 (10)	0.073 (2)
H5	−0.4150	0.6047	1.0887	0.087*
C6	−0.1256 (11)	0.5303 (4)	0.9858 (8)	0.0639 (16)
H6	−0.0652	0.5052	1.0904	0.077*
C7	0.2044 (10)	0.4416 (3)	0.8361 (7)	0.0480 (14)
H7	0.2592	0.4179	0.9431	0.058*
C8	0.5180 (10)	0.3518 (3)	0.7054 (6)	0.0431 (14)
C9	0.6040 (10)	0.3216 (3)	0.5473 (7)	0.0526 (15)
C10	0.7977 (11)	0.2575 (4)	0.5400 (8)	0.0657 (17)
H10	0.8484	0.2375	0.4326	0.079*
C11	0.9127 (13)	0.2241 (4)	0.6912 (9)	0.0685 (18)
H11	1.0417	0.1812	0.6877	0.082*
C12	0.8365 (11)	0.2546 (4)	0.8477 (9)	0.0623 (17)
H12	0.9182	0.2324	0.9503	0.075*
C13	0.6393 (11)	0.3180 (3)	0.8582 (7)	0.0565 (15)
H13	0.5899	0.3373	0.9664	0.068*
C14	0.4758 (15)	0.3547 (5)	0.3888 (9)	0.093 (2)
N1	0.3182 (9)	0.4157 (2)	0.6972 (5)	0.0459 (11)
N2	0.3736 (15)	0.3796 (5)	0.2608 (8)	0.147 (3)
O1	0.0028 (9)	0.5256 (3)	0.5203 (5)	0.0815 (14)
H1	0.1174	0.4881	0.5348	0.122*

	U11	U22	U33	U12	U13	U23
C1	0.040 (3)	0.047 (4)	0.055 (4)	−0.003 (3)	0.005 (3)	−0.002 (3)
C2	0.052 (3)	0.044 (4)	0.079 (5)	0.005 (3)	0.013 (3)	0.011 (3)
C3	0.067 (5)	0.068 (5)	0.094 (6)	0.010 (4)	0.014 (4)	0.020 (4)
C4	0.063 (4)	0.043 (4)	0.119 (6)	0.012 (4)	0.013 (4)	−0.001 (4)
C5	0.051 (4)	0.079 (5)	0.089 (5)	0.002 (3)	0.014 (4)	−0.029 (4)
C6	0.054 (4)	0.075 (5)	0.062 (4)	−0.004 (4)	−0.002 (3)	−0.020 (3)
C7	0.043 (3)	0.053 (4)	0.047 (4)	0.002 (3)	−0.003 (2)	−0.005 (3)
C8	0.046 (3)	0.042 (4)	0.042 (3)	−0.002 (3)	0.004 (2)	−0.006 (2)
C9	0.050 (3)	0.060 (4)	0.048 (4)	0.004 (3)	0.001 (3)	0.003 (3)
C10	0.065 (4)	0.068 (5)	0.065 (4)	0.009 (3)	0.005 (3)	−0.017 (3)
C11	0.060 (4)	0.072 (5)	0.073 (5)	0.007 (4)	0.004 (3)	−0.005 (4)
C12	0.056 (4)	0.052 (4)	0.080 (5)	0.010 (3)	0.006 (3)	0.017 (3)
C13	0.059 (4)	0.061 (4)	0.050 (4)	0.006 (3)	0.010 (3)	0.007 (3)
C14	0.093 (5)	0.135 (7)	0.052 (4)	0.042 (5)	0.005 (4)	−0.012 (4)
N1	0.049 (3)	0.041 (3)	0.048 (3)	−0.003 (2)	0.0079 (19)	0.000 (2)
N2	0.162 (7)	0.225 (9)	0.053 (4)	0.106 (6)	−0.002 (4)	0.010 (5)
O1	0.085 (3)	0.092 (4)	0.069 (3)	0.028 (2)	0.020 (2)	0.030 (2)

C1—C6	1.405 (7)	C8—C13	1.389 (7)
C1—C2	1.406 (7)	C8—C9	1.391 (6)
C1—C7	1.450 (6)	C8—N1	1.406 (6)
C2—O1	1.345 (7)	C9—C10	1.393 (7)
C2—C3	1.385 (8)	C9—C14	1.433 (9)
C3—C4	1.363 (9)	C10—C11	1.365 (8)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.381 (9)	C11—C12	1.366 (8)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.387 (8)	C12—C13	1.397 (7)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.293 (5)	C14—N2	1.144 (7)
C7—H7	0.9300	O1—H1	0.8200
C6—C1—C2	118.3 (5)	C13—C8—C9	117.9 (5)
C6—C1—C7	119.1 (5)	C13—C8—N1	125.2 (5)
C2—C1—C7	122.6 (5)	C9—C8—N1	116.9 (4)
O1—C2—C3	118.5 (6)	C8—C9—C10	121.8 (5)
O1—C2—C1	121.7 (5)	C8—C9—C14	118.4 (5)
C3—C2—C1	119.8 (6)	C10—C9—C14	119.7 (5)
C4—C3—C2	120.5 (6)	C11—C10—C9	119.7 (6)
C4—C3—H3	119.8	C11—C10—H10	120.2
C2—C3—H3	119.8	C9—C10—H10	120.2
C3—C4—C5	121.6 (6)	C10—C11—C12	119.3 (6)
C3—C4—H4	119.2	C10—C11—H11	120.3
C5—C4—H4	119.2	C12—C11—H11	120.3
C4—C5—C6	118.6 (6)	C11—C12—C13	122.0 (6)
C4—C5—H5	120.7	C11—C12—H12	119.0
C6—C5—H5	120.7	C13—C12—H12	119.0
C5—C6—C1	121.2 (6)	C8—C13—C12	119.3 (5)
C5—C6—H6	119.4	C8—C13—H13	120.3
C1—C6—H6	119.4	C12—C13—H13	120.3
N1—C7—C1	122.1 (4)	N2—C14—C9	178.6 (8)
N1—C7—H7	118.9	C7—N1—C8	121.1 (4)
C1—C7—H7	118.9	C2—O1—H1	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.651 (6)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.651 (6)	147