3-(2-Hydroxy-benzyl-ideneamino)benzonitrile.

In the title mol-ecule, C(14)H(10)N(2)O, an intra-molecular O-H⋯N hydrogen bond contributes to the essential coplanarity of the two benzene rings, which form a dihedral angle of 6.04 (18)°.

Related literature

For related crystal structures, see: Kosar et al. (2005 ▶); Cheng et al. (2005 ▶, 2006 ▶).

Experimental

Crystal data

C14H10N2O

M = 222.24

Orthorhombic,

a = 26.397 (5) Å

b = 3.9211 (8) Å

c = 10.773 (2) Å

V = 1115.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.22 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.812, T max = 1.000 (expected range = 0.809–0.996)

9995 measured reflections

1339 independent reflections

901 reflections with I > 2σ(I)

R int = 0.116

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.121

S = 1.05

1339 reflections

160 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 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/S1600536808005242/cv2384sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005242/cv2384Isup2.hkl

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

C14H10N2O	F000 = 464
Mr = 222.24	Dx = 1.324 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 8294 reflections
a = 26.397 (5) Å	θ = 3.0–27.6º
b = 3.9211 (8) Å	µ = 0.09 mm−1
c = 10.773 (2) Å	T = 293 (2) K
V = 1115.1 (4) Å3	Stick, yellow
Z = 4	0.22 × 0.05 × 0.05 mm

Rigaku Mercury2 diffractometer	1339 independent reflections
Radiation source: fine-focus sealed tube	901 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.116
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
ω scans	h = −34→34
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −5→5
Tmin = 0.812, Tmax = 1.00	l = −13→13
9995 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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0413P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1339 reflections	Δρmax = 0.15 e Å−3
160 parameters	Δρmin = −0.16 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.45687 (11)	0.2218 (7)	0.2697 (3)	0.0473 (8)
C1	0.54425 (12)	0.2407 (8)	0.3273 (3)	0.0427 (8)
C9	0.37076 (12)	0.2616 (9)	0.2071 (3)	0.0457 (9)
H9A	0.3823	0.3718	0.1360	0.055*
C6	0.57995 (14)	0.1614 (9)	0.4188 (3)	0.0559 (10)
H6A	0.5694	0.0602	0.4924	0.067*
C8	0.40534 (12)	0.1480 (8)	0.2952 (3)	0.0451 (8)
C7	0.49124 (12)	0.1608 (8)	0.3501 (3)	0.0460 (9)
H7A	0.4821	0.0624	0.4254	0.055*
C3	0.61133 (14)	0.4649 (10)	0.2017 (3)	0.0570 (11)
H3A	0.6223	0.5715	0.1294	0.068*
C2	0.56072 (13)	0.3894 (9)	0.2167 (3)	0.0468 (9)
C12	0.33597 (14)	−0.0682 (10)	0.4162 (4)	0.0601 (10)
H12A	0.3245	−0.1800	0.4869	0.072*
C10	0.31905 (13)	0.2118 (9)	0.2243 (3)	0.0510 (10)
C11	0.30193 (13)	0.0476 (9)	0.3297 (3)	0.0572 (11)
H11A	0.2674	0.0157	0.3421	0.069*
C14	0.28378 (13)	0.3427 (10)	0.1343 (4)	0.0585 (10)
O1	0.52789 (11)	0.4688 (8)	0.1250 (3)	0.0683 (8)
C5	0.63050 (14)	0.2312 (10)	0.4013 (4)	0.0629 (11)
H5A	0.6540	0.1756	0.4622	0.076*
C4	0.64585 (14)	0.3839 (10)	0.2928 (4)	0.0632 (11)
H4A	0.6800	0.4331	0.2808	0.076*
C13	0.38733 (13)	−0.0193 (10)	0.3986 (3)	0.0542 (10)
H13A	0.4101	−0.1006	0.4575	0.065*
N2	0.25591 (14)	0.4542 (10)	0.0648 (4)	0.0896 (13)
H1B	0.4999 (10)	0.396 (12)	0.145 (7)	0.13 (2)*

	U11	U22	U33	U12	U13	U23
N1	0.0426 (18)	0.0517 (18)	0.0474 (16)	0.0006 (13)	−0.0038 (14)	−0.0007 (13)
C1	0.038 (2)	0.0449 (17)	0.045 (2)	0.0021 (14)	0.0015 (17)	−0.0035 (16)
C9	0.042 (2)	0.048 (2)	0.046 (2)	0.0029 (16)	0.0022 (17)	−0.0027 (17)
C6	0.053 (2)	0.058 (2)	0.057 (2)	0.0006 (18)	−0.005 (2)	0.0031 (19)
C8	0.0392 (19)	0.0456 (19)	0.051 (2)	−0.0018 (15)	0.0032 (17)	−0.0088 (17)
C7	0.052 (2)	0.0445 (19)	0.042 (2)	0.0000 (16)	0.0045 (17)	0.0015 (17)
C3	0.054 (3)	0.061 (3)	0.056 (2)	−0.0065 (18)	0.0091 (19)	−0.0002 (19)
C2	0.047 (2)	0.051 (2)	0.042 (2)	−0.0009 (16)	0.0012 (16)	−0.0012 (18)
C12	0.056 (2)	0.065 (3)	0.060 (2)	−0.0083 (19)	0.006 (2)	0.006 (2)
C10	0.042 (2)	0.054 (2)	0.057 (2)	0.0035 (17)	0.0024 (19)	−0.0148 (19)
C11	0.0399 (19)	0.061 (2)	0.071 (3)	−0.0074 (17)	0.0068 (19)	−0.013 (2)
C14	0.044 (2)	0.065 (3)	0.067 (2)	0.0038 (18)	−0.006 (2)	−0.011 (2)
O1	0.0590 (17)	0.092 (2)	0.0540 (15)	−0.0015 (16)	−0.0059 (17)	0.0190 (16)
C5	0.049 (2)	0.070 (3)	0.070 (3)	0.007 (2)	−0.011 (2)	0.002 (2)
C4	0.047 (2)	0.064 (2)	0.079 (3)	−0.0066 (19)	0.004 (2)	−0.008 (2)
C13	0.047 (2)	0.060 (2)	0.056 (2)	−0.0005 (17)	0.0015 (18)	0.007 (2)
N2	0.066 (2)	0.097 (3)	0.105 (3)	0.012 (2)	−0.032 (2)	−0.004 (2)

N1—C7	1.277 (4)	C3—H3A	0.9300
N1—C8	1.418 (4)	C2—O1	1.351 (4)
C1—C2	1.396 (4)	C12—C11	1.372 (5)
C1—C6	1.398 (5)	C12—C13	1.382 (5)
C1—C7	1.455 (4)	C12—H12A	0.9300
C9—C8	1.390 (4)	C10—C11	1.381 (5)
C9—C10	1.391 (4)	C10—C14	1.439 (5)
C9—H9A	0.9300	C11—H11A	0.9300
C6—C5	1.375 (5)	C14—N2	1.137 (5)
C6—H6A	0.9300	O1—H1B	0.82 (2)
C8—C13	1.377 (5)	C5—C4	1.374 (5)
C7—H7A	0.9300	C5—H5A	0.9300
C3—C4	1.376 (5)	C4—H4A	0.9300
C3—C2	1.378 (4)	C13—H13A	0.9300
C7—N1—C8	120.8 (3)	C3—C2—C1	119.5 (3)
C2—C1—C6	119.0 (3)	C11—C12—C13	120.2 (3)
C2—C1—C7	122.2 (3)	C11—C12—H12A	119.9
C6—C1—C7	118.8 (3)	C13—C12—H12A	119.9
C8—C9—C10	120.5 (3)	C11—C10—C9	119.8 (3)
C8—C9—H9A	119.7	C11—C10—C14	120.6 (3)
C10—C9—H9A	119.7	C9—C10—C14	119.6 (4)
C5—C6—C1	120.9 (4)	C12—C11—C10	119.9 (3)
C5—C6—H6A	119.6	C12—C11—H11A	120.1
C1—C6—H6A	119.6	C10—C11—H11A	120.1
C13—C8—C9	118.6 (3)	N2—C14—C10	178.2 (5)
C13—C8—N1	125.8 (3)	C2—O1—H1B	108 (5)
C9—C8—N1	115.6 (3)	C4—C5—C6	119.3 (4)
N1—C7—C1	121.9 (3)	C4—C5—H5A	120.4
N1—C7—H7A	119.0	C6—C5—H5A	120.4
C1—C7—H7A	119.0	C3—C4—C5	120.8 (3)
C4—C3—C2	120.5 (4)	C3—C4—H4A	119.6
C4—C3—H3A	119.7	C5—C4—H4A	119.6
C2—C3—H3A	119.7	C12—C13—C8	121.0 (3)
O1—C2—C3	119.1 (3)	C12—C13—H13A	119.5
O1—C2—C1	121.4 (3)	C8—C13—H13A	119.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1	0.82 (2)	1.89 (4)	2.623 (4)	149 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N1	0.82 (2)	1.89 (4)	2.623 (4)	149 (7)