(E)-2-(2,4-Dihydroxy-benzyl-ideneamino)benzonitrile.

The mol-ecule of the title compound, C(14)H(10)N(2)O(2), adopts the phenol-imine tautomeric form. The dihedral angle between the planes of the two benzene rings is 13.84 (13)°. A strong intra-molecular O-H⋯N hydrogen-bonding inter-action stabilizes the mol-ecular conformation. In the crystal structure, centrosymmetrically related mol-ecules are linked into dimers by inter-molecular C-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Cheng et al. (2006 ▶); Xia et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10N2O2

M = 238.24

Monoclinic,

a = 13.322 (3) Å

b = 5.7505 (12) Å

c = 16.132 (3) Å

β = 108.97 (3)°

V = 1168.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.973, T max = 0.979

11536 measured reflections

2683 independent reflections

1394 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.153

S = 1.01

2683 reflections

167 parameters

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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020182/rz2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020182/rz2327Isup2.hkl

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

C14H10N2O2	F(000) = 496
Mr = 238.24	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8059 reflections
a = 13.322 (3) Å	θ = 3.1–27.8°
b = 5.7505 (12) Å	µ = 0.09 mm−1
c = 16.132 (3) Å	T = 293 K
β = 108.97 (3)°	Prism, yellow
V = 1168.7 (5) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2683 independent reflections
Radiation source: fine-focus sealed tube	1394 reflections with I > 2σ(I)
graphite	Rint = 0.073
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→7
Tmin = 0.973, Tmax = 0.979	l = −20→20
11536 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0648P)2] where P = (Fo2 + 2Fc2)/3
2683 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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
O2	0.79346 (11)	0.8933 (3)	0.08149 (11)	0.0566 (5)
H2A	0.7911	0.7663	0.0578	0.085*
N2	0.33856 (14)	0.9483 (3)	0.12987 (11)	0.0458 (5)
O1	0.45029 (14)	0.6553 (3)	0.07575 (12)	0.0620 (5)
C8	0.41862 (18)	1.0886 (4)	0.14982 (14)	0.0467 (6)
H8A	0.4127	1.2327	0.1740	0.056*
C9	0.51588 (16)	1.0290 (4)	0.13590 (13)	0.0413 (5)
C12	0.70129 (17)	0.9304 (4)	0.09842 (14)	0.0430 (6)
C5	0.1263 (2)	1.2217 (5)	0.20046 (18)	0.0709 (8)
H5A	0.1164	1.3435	0.2349	0.085*
C3	0.05604 (19)	0.8978 (5)	0.10712 (18)	0.0643 (7)
H3A	−0.0004	0.8009	0.0784	0.077*
C1	0.24136 (18)	1.0047 (4)	0.14176 (14)	0.0466 (6)
C10	0.52810 (17)	0.8164 (4)	0.09675 (14)	0.0434 (6)
C14	0.60082 (18)	1.1854 (4)	0.15679 (15)	0.0506 (6)
H14A	0.5947	1.3258	0.1834	0.061*
C11	0.61972 (16)	0.7695 (4)	0.07767 (14)	0.0447 (6)
H11A	0.6266	0.6300	0.0509	0.054*
C13	0.69260 (18)	1.1384 (4)	0.13929 (15)	0.0514 (6)
H13A	0.7484	1.2443	0.1545	0.062*
C2	0.15547 (18)	0.8609 (4)	0.09949 (15)	0.0500 (6)
C7	0.17047 (19)	0.6737 (5)	0.04576 (18)	0.0575 (7)
N1	0.18114 (18)	0.5237 (4)	0.00325 (17)	0.0777 (8)
C6	0.22459 (19)	1.1855 (5)	0.19264 (16)	0.0598 (7)
H6A	0.2806	1.2832	0.2218	0.072*
C4	0.0418 (2)	1.0796 (5)	0.15775 (18)	0.0707 (8)
H4A	−0.0247	1.1065	0.1632	0.085*
H1A	0.392 (2)	0.729 (5)	0.0876 (17)	0.090 (10)*

	U11	U22	U33	U12	U13	U23
O2	0.0453 (10)	0.0602 (11)	0.0695 (12)	−0.0039 (8)	0.0261 (8)	−0.0088 (8)
N2	0.0384 (10)	0.0558 (12)	0.0429 (11)	0.0041 (10)	0.0130 (8)	−0.0002 (9)
O1	0.0445 (10)	0.0547 (11)	0.0895 (14)	−0.0107 (9)	0.0256 (9)	−0.0253 (9)
C8	0.0512 (14)	0.0476 (14)	0.0432 (14)	0.0018 (12)	0.0179 (11)	−0.0039 (10)
C9	0.0415 (13)	0.0418 (13)	0.0405 (13)	−0.0001 (11)	0.0133 (10)	−0.0021 (10)
C12	0.0384 (12)	0.0508 (14)	0.0401 (13)	−0.0001 (11)	0.0131 (10)	0.0016 (10)
C5	0.0568 (16)	0.096 (2)	0.0643 (18)	0.0081 (17)	0.0256 (14)	−0.0210 (16)
C3	0.0468 (15)	0.0802 (19)	0.0698 (18)	−0.0065 (14)	0.0241 (13)	−0.0108 (15)
C1	0.0435 (13)	0.0595 (15)	0.0386 (13)	0.0060 (12)	0.0155 (10)	0.0039 (11)
C10	0.0397 (13)	0.0443 (13)	0.0429 (13)	−0.0042 (11)	0.0092 (10)	−0.0004 (10)
C14	0.0545 (15)	0.0418 (14)	0.0574 (15)	−0.0033 (12)	0.0209 (12)	−0.0087 (11)
C11	0.0422 (13)	0.0449 (13)	0.0468 (13)	0.0001 (11)	0.0142 (10)	−0.0082 (10)
C13	0.0472 (14)	0.0504 (15)	0.0598 (16)	−0.0117 (12)	0.0218 (12)	−0.0073 (12)
C2	0.0448 (14)	0.0572 (15)	0.0507 (15)	0.0011 (12)	0.0192 (11)	−0.0018 (12)
C7	0.0501 (15)	0.0586 (17)	0.0681 (18)	−0.0079 (13)	0.0252 (13)	−0.0053 (14)
N1	0.0735 (17)	0.0691 (16)	0.0994 (19)	−0.0109 (14)	0.0406 (14)	−0.0236 (15)
C6	0.0499 (15)	0.0781 (19)	0.0521 (15)	−0.0044 (14)	0.0176 (12)	−0.0176 (14)
C4	0.0499 (16)	0.099 (2)	0.0692 (19)	0.0031 (16)	0.0278 (14)	−0.0109 (16)

O2—C12	1.359 (2)	C3—C4	1.377 (3)
O2—H2A	0.8200	C3—C2	1.386 (3)
N2—C8	1.292 (3)	C3—H3A	0.9300
N2—C1	1.407 (3)	C1—C6	1.387 (3)
O1—C10	1.349 (3)	C1—C2	1.397 (3)
O1—H1A	0.95 (3)	C10—C11	1.379 (3)
C8—C9	1.427 (3)	C14—C13	1.368 (3)
C8—H8A	0.9300	C14—H14A	0.9300
C9—C14	1.398 (3)	C11—H11A	0.9300
C9—C10	1.409 (3)	C13—H13A	0.9300
C12—C11	1.383 (3)	C2—C7	1.436 (3)
C12—C13	1.389 (3)	C7—N1	1.139 (3)
C5—C6	1.372 (3)	C6—H6A	0.9300
C5—C4	1.380 (4)	C4—H4A	0.9300
C5—H5A	0.9300
C12—O2—H2A	109.5	O1—C10—C9	121.1 (2)
C8—N2—C1	123.0 (2)	C11—C10—C9	120.6 (2)
C10—O1—H1A	104.5 (17)	C13—C14—C9	122.0 (2)
N2—C8—C9	122.0 (2)	C13—C14—H14A	119.0
N2—C8—H8A	119.0	C9—C14—H14A	119.0
C9—C8—H8A	119.0	C12—C11—C10	119.9 (2)
C14—C9—C10	117.6 (2)	C12—C11—H11A	120.1
C14—C9—C8	120.9 (2)	C10—C11—H11A	120.1
C10—C9—C8	121.5 (2)	C14—C13—C12	119.1 (2)
O2—C12—C11	122.5 (2)	C14—C13—H13A	120.5
O2—C12—C13	116.8 (2)	C12—C13—H13A	120.5
C11—C12—C13	120.7 (2)	C3—C2—C1	121.4 (2)
C6—C5—C4	120.8 (3)	C3—C2—C7	119.5 (2)
C6—C5—H5A	119.6	C1—C2—C7	119.1 (2)
C4—C5—H5A	119.6	N1—C7—C2	179.0 (3)
C4—C3—C2	119.3 (2)	C5—C6—C1	120.7 (2)
C4—C3—H3A	120.4	C5—C6—H6A	119.7
C2—C3—H3A	120.4	C1—C6—H6A	119.7
C6—C1—C2	117.9 (2)	C3—C4—C5	119.9 (2)
C6—C1—N2	125.9 (2)	C3—C4—H4A	120.1
C2—C1—N2	116.2 (2)	C5—C4—H4A	120.1
O1—C10—C11	118.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.95 (3)	1.70 (3)	2.581 (2)	152 (3)
O2—H2A···N1i	0.82	2.03	2.835 (3)	166
C11—H11A···O1i	0.93	2.56	3.386 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2	0.95 (3)	1.70 (3)	2.581 (2)	152 (3)
O2—H2A⋯N1i	0.82	2.03	2.835 (3)	166
C11—H11A⋯O1i	0.93	2.56	3.386 (3)	148

Symmetry code: (i) .