4-(2-Hydroxy-benzyl-idene-amino)-benzonitrile.

The mol-ecule of the title compound, C(14)H(10)N(2)O, is nearly planar. There is a strong intra-molecular O-H⋯N hydrogen bond between the imine and hydr-oxy groups. The configuration with respect to the C=N double bond is anti (1E).

Related literature

For related literature, see: Allen et al. (1987 ▶); Chen et al. (2008 ▶); Cheng et al. (2005 ▶, 2006 ▶); Elmah et al. (1999 ▶); May et al. (2004 ▶); Weber et al. (2007 ▶); Xu et al. (2008 ▶).

Experimental

Crystal data

C14H10N2O

M = 222.24

Monoclinic,

a = 28.071 (6) Å

b = 5.8471 (12) Å

c = 14.687 (3) Å

β = 109.91 (3)°

V = 2266.6 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.12 × 0.11 × 0.03 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.915, T max = 1.00 (expected range = 0.913–0.997)

9782 measured reflections

2223 independent reflections

971 reflections with I > 2σ(I)

R int = 0.132

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.176

S = 0.97

2223 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.18 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801564X/dn2347sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801564X/dn2347Isup2.hkl

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

C14H10N2O	F000 = 928
Mr = 222.24	Dx = 1.303 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7031 reflections
a = 28.071 (6) Å	θ = 3.1–29.0º
b = 5.8471 (12) Å	µ = 0.08 mm−1
c = 14.687 (3) Å	T = 293 (2) K
β = 109.91 (3)º	Block, yellow
V = 2266.6 (9) Å3	0.12 × 0.11 × 0.03 mm
Z = 8

Rigaku Mercury2 (2x2 bin mode) diffractometer	2223 independent reflections
Radiation source: fine-focus sealed tube	971 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.132
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 3.5º
ω scans	h = −34→34
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −7→7
Tmin = 0.915, Tmax = 1.00	l = −18→18
9782 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)] = 0.077	H-atom parameters constrained
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2223 reflections	Δρmax = 0.18 e Å−3
154 parameters	Δρmin = −0.18 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 > 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
C13	0.34671 (13)	0.0317 (6)	0.9348 (3)	0.0487 (10)
H14A	0.3362	−0.0983	0.9592	0.058*
C7	0.22581 (13)	0.3041 (6)	0.8582 (2)	0.0466 (10)
H13A	0.2331	0.4471	0.8385	0.056*
N1	0.26153 (10)	0.1571 (4)	0.8889 (2)	0.0443 (8)
C3	0.11223 (12)	0.0032 (6)	0.8792 (3)	0.0504 (10)
H12A	0.1038	−0.1343	0.9017	0.061*
C10	0.37793 (13)	0.4177 (6)	0.8639 (3)	0.0527 (11)
H11A	0.3889	0.5492	0.8414	0.063*
C11	0.41195 (13)	0.2453 (7)	0.9055 (3)	0.0479 (10)
C8	0.31195 (12)	0.1997 (6)	0.8920 (2)	0.0396 (9)
C9	0.32765 (13)	0.3953 (6)	0.8557 (3)	0.0485 (10)
H8A	0.3045	0.5095	0.8262	0.058*
O1	0.19746 (9)	−0.1128 (4)	0.92932 (18)	0.0630 (8)
H1B	0.2253	−0.0677	0.9302	0.095*
C2	0.16187 (13)	0.0481 (6)	0.8873 (3)	0.0439 (9)
C1	0.17471 (12)	0.2547 (6)	0.8532 (2)	0.0384 (9)
C6	0.13639 (13)	0.4125 (6)	0.8116 (3)	0.0497 (10)
H5A	0.1444	0.5505	0.7888	0.060*
C14	0.46381 (14)	0.2676 (6)	0.9108 (3)	0.0591 (12)
C12	0.39627 (13)	0.0523 (6)	0.9420 (3)	0.0522 (10)
H3A	0.4193	−0.0625	0.9713	0.063*
C4	0.07550 (14)	0.1627 (7)	0.8377 (3)	0.0545 (11)
H2A	0.0422	0.1319	0.8323	0.065*
C5	0.08702 (14)	0.3697 (7)	0.8034 (3)	0.0602 (12)
H1A	0.0618	0.4769	0.7754	0.072*
N2	0.50503 (13)	0.2785 (6)	0.9144 (3)	0.0899 (13)

	U11	U22	U33	U12	U13	U23
C13	0.052 (2)	0.041 (2)	0.055 (3)	0.0006 (19)	0.020 (2)	0.0061 (19)
C7	0.058 (3)	0.045 (2)	0.038 (2)	−0.009 (2)	0.0190 (19)	0.0019 (18)
N1	0.0419 (17)	0.0436 (18)	0.048 (2)	−0.0016 (15)	0.0161 (15)	0.0017 (15)
C3	0.051 (2)	0.051 (2)	0.051 (3)	−0.007 (2)	0.019 (2)	0.003 (2)
C10	0.055 (2)	0.052 (2)	0.056 (3)	−0.011 (2)	0.026 (2)	0.001 (2)
C11	0.042 (2)	0.055 (2)	0.049 (2)	−0.005 (2)	0.0189 (19)	0.001 (2)
C8	0.038 (2)	0.046 (2)	0.036 (2)	−0.0043 (18)	0.0143 (17)	−0.0006 (18)
C9	0.049 (2)	0.046 (2)	0.051 (3)	0.0014 (19)	0.0181 (19)	0.0106 (19)
O1	0.0538 (17)	0.0503 (16)	0.087 (2)	0.0003 (13)	0.0273 (15)	0.0197 (14)
C2	0.042 (2)	0.045 (2)	0.044 (2)	0.0030 (19)	0.0135 (19)	0.0047 (18)
C1	0.038 (2)	0.042 (2)	0.035 (2)	−0.0046 (18)	0.0124 (17)	−0.0021 (17)
C6	0.049 (2)	0.050 (2)	0.053 (3)	−0.001 (2)	0.0212 (19)	0.009 (2)
C14	0.045 (3)	0.061 (3)	0.070 (3)	0.002 (2)	0.017 (2)	0.009 (2)
C12	0.044 (2)	0.050 (2)	0.062 (3)	0.0027 (19)	0.017 (2)	0.005 (2)
C4	0.042 (2)	0.069 (3)	0.056 (3)	−0.003 (2)	0.021 (2)	0.003 (2)
C5	0.054 (3)	0.065 (3)	0.063 (3)	0.014 (2)	0.021 (2)	0.010 (2)
N2	0.050 (2)	0.097 (3)	0.124 (4)	0.002 (2)	0.033 (2)	0.029 (3)

C13—C12	1.364 (4)	C11—C14	1.437 (5)
C13—C8	1.376 (4)	C8—C9	1.395 (4)
C13—H14A	0.9300	C9—H8A	0.9300
C7—N1	1.280 (4)	O1—C2	1.358 (4)
C7—C1	1.440 (4)	O1—H1B	0.8200
C7—H13A	0.9300	C2—C1	1.401 (4)
N1—C8	1.422 (4)	C1—C6	1.391 (4)
C3—C4	1.370 (4)	C6—C5	1.373 (4)
C3—C2	1.383 (4)	C6—H5A	0.9300
C3—H12A	0.9300	C14—N2	1.142 (4)
C10—C11	1.380 (5)	C12—H3A	0.9300
C10—C9	1.381 (4)	C4—C5	1.391 (5)
C10—H11A	0.9300	C4—H2A	0.9300
C11—C12	1.384 (4)	C5—H1A	0.9300
C12—C13—C8	121.2 (3)	C8—C9—H8A	120.3
C12—C13—H14A	119.4	C2—O1—H1B	109.5
C8—C13—H14A	119.4	O1—C2—C3	118.1 (3)
N1—C7—C1	122.0 (3)	O1—C2—C1	121.4 (3)
N1—C7—H13A	119.0	C3—C2—C1	120.5 (3)
C1—C7—H13A	119.0	C6—C1—C2	118.3 (3)
C7—N1—C8	123.0 (3)	C6—C1—C7	119.8 (3)
C4—C3—C2	119.5 (3)	C2—C1—C7	121.8 (3)
C4—C3—H12A	120.2	C5—C6—C1	121.6 (3)
C2—C3—H12A	120.2	C5—C6—H5A	119.2
C11—C10—C9	120.1 (3)	C1—C6—H5A	119.2
C11—C10—H11A	119.9	N2—C14—C11	178.0 (5)
C9—C10—H11A	119.9	C13—C12—C11	119.5 (3)
C10—C11—C12	120.2 (3)	C13—C12—H3A	120.3
C10—C11—C14	119.5 (3)	C11—C12—H3A	120.3
C12—C11—C14	120.2 (4)	C3—C4—C5	121.4 (3)
C13—C8—C9	119.5 (3)	C3—C4—H2A	119.3
C13—C8—N1	115.6 (3)	C5—C4—H2A	119.3
C9—C8—N1	124.9 (3)	C6—C5—C4	118.6 (3)
C10—C9—C8	119.4 (3)	C6—C5—H1A	120.7
C10—C9—H8A	120.3	C4—C5—H1A	120.7

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1	0.82	1.88	2.609 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N1	0.82	1.88	2.609 (4)	147