4-[(2E)-2-(2-Hy-droxy-benzyl-idene)hydrazin-1-yl]benzonitrile.

The asymmetric unit of the title Schiff base, C(14)H(11)N(3)O, contains two independent mol-ecules which have similar conformations. The dihedral angles between the benzene rings are 4.19 (9) and 14.18 (9)° in the two mol-ecules. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation of each mol-ecules. The crystal packing is dominated by pairs of equivalent N-H⋯N and C-H⋯O hydrogen bonds which arrange the mol-ecules into layers parallel to (-111).

Related literature

For azomethines, see: Archibald et al. (1994 ▶); Harada et al. (1999 ▶); Ogawa et al. (1998 ▶). For the biological properties of Schiff bases, see: Lozier et al. (1975 ▶); Dao et al. (2000 ▶). For their coordination chemistry, see: Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For the structure of related Schiff bases reported by our group, see: Mohamed, Abdelhamid et al. (2012 ▶); Mohamed, Akkurt et al. (2012 ▶).

Experimental

Crystal data

C14H11N3O

M = 237.26

Triclinic,

a = 8.1917 (7) Å

b = 11.6406 (7) Å

c = 13.4445 (8) Å

α = 103.006 (5)°

β = 104.387 (6)°

γ = 96.426 (6)°

V = 1190.67 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.70 mm−1

T = 293 K

0.26 × 0.15 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.827, T max = 1.000

7913 measured reflections

4592 independent reflections

3696 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.05

4592 reflections

341 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶)’; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037841/rz2800sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037841/rz2800Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037841/rz2800Isup3.cml

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

C14H11N3O	Z = 4
Mr = 237.26	F(000) = 496
Triclinic, P1	Dx = 1.324 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 8.1917 (7) Å	Cell parameters from 3110 reflections
b = 11.6406 (7) Å	θ = 3.5–72.5°
c = 13.4445 (8) Å	µ = 0.70 mm−1
α = 103.006 (5)°	T = 293 K
β = 104.387 (6)°	Prismatic, colorless
γ = 96.426 (6)°	0.26 × 0.15 × 0.14 mm
V = 1190.67 (14) Å3

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer	4592 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3696 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 16.3280 pixels mm-1	θmax = 72.6°, θmin = 3.5°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→13
Tmin = 0.827, Tmax = 1.000	l = −16→14
7913 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.1257P] where P = (Fo2 + 2Fc2)/3
4592 reflections	(Δ/σ)max < 0.001
341 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Experimental. Absorption correction: Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 'CrysAlisPro (Oxford Diffraction, 2009)'

	x	y	z	Uiso*/Ueq
O1A	0.48536 (17)	0.59328 (11)	0.66183 (10)	0.0784 (4)
O1B	0.91964 (17)	−0.08146 (11)	0.25880 (10)	0.0774 (4)
N1A	0.22126 (15)	0.44483 (11)	0.51588 (9)	0.0526 (3)
N1B	0.93383 (15)	0.06285 (11)	0.13286 (9)	0.0522 (3)
N2A	0.09712 (17)	0.40478 (12)	0.42146 (10)	0.0596 (3)
N2B	0.87286 (17)	0.10497 (12)	0.04621 (10)	0.0602 (3)
N3A	−0.0385 (2)	0.69952 (14)	0.03913 (11)	0.0808 (5)
N3B	0.20536 (19)	−0.19989 (13)	−0.37048 (11)	0.0718 (4)
C1A	0.22866 (18)	0.37735 (12)	0.58006 (11)	0.0515 (3)
H1A	0.1506	0.3060	0.5593	0.062*
C1B	1.06978 (18)	0.12410 (12)	0.20323 (11)	0.0497 (3)
H1B	1.1242	0.1924	0.1917	0.060*
C2A	0.35367 (18)	0.40831 (12)	0.68322 (11)	0.0480 (3)
C2B	1.14175 (17)	0.09042 (12)	0.30040 (11)	0.0475 (3)
C3A	0.47572 (19)	0.51421 (13)	0.72128 (12)	0.0536 (3)
C3B	1.0654 (2)	−0.00961 (13)	0.32475 (12)	0.0549 (3)
C4A	0.5895 (2)	0.54087 (15)	0.82180 (13)	0.0662 (4)
H4A	0.6707	0.6109	0.8464	0.079*
C4B	1.1394 (2)	−0.03657 (15)	0.41970 (13)	0.0676 (4)
H4B	1.0883	−0.1025	0.4362	0.081*
C5A	0.5828 (2)	0.46422 (17)	0.88535 (13)	0.0706 (5)
H5A	0.6591	0.4832	0.9531	0.085*
C5B	1.2868 (2)	0.03347 (17)	0.48887 (13)	0.0735 (5)
H5B	1.3355	0.0142	0.5519	0.088*
C6A	0.4644 (2)	0.35943 (17)	0.84996 (13)	0.0703 (4)
H6A	0.4605	0.3079	0.8934	0.084*
C6B	1.3643 (2)	0.13218 (16)	0.46669 (13)	0.0695 (4)
H6B	1.4646	0.1793	0.5142	0.083*
C7A	0.3520 (2)	0.33197 (14)	0.74959 (12)	0.0600 (4)
H7A	0.2730	0.2608	0.7254	0.072*
C7B	1.29124 (19)	0.16031 (14)	0.37294 (12)	0.0574 (4)
H7B	1.3429	0.2272	0.3580	0.069*
C8A	0.07493 (18)	0.46900 (12)	0.34649 (11)	0.0511 (3)
C8B	0.73501 (18)	0.04005 (13)	−0.03593 (11)	0.0507 (3)
C9A	0.1698 (2)	0.58289 (14)	0.36363 (12)	0.0589 (4)
H9A	0.2530	0.6184	0.4279	0.071*
C9B	0.66057 (19)	−0.07671 (13)	−0.04234 (12)	0.0549 (3)
H9B	0.7039	−0.1134	0.0108	0.066*
C10A	0.1391 (2)	0.64216 (14)	0.28470 (12)	0.0622 (4)
H10A	0.2015	0.7182	0.2965	0.075*
C10B	0.5233 (2)	−0.13687 (13)	−0.12740 (12)	0.0571 (4)
H10B	0.4750	−0.2146	−0.1314	0.068*
C11A	0.0169 (2)	0.59024 (13)	0.18796 (12)	0.0558 (4)
C11B	0.45513 (19)	−0.08366 (13)	−0.20774 (11)	0.0539 (3)
C12A	−0.0775 (2)	0.47666 (14)	0.17121 (12)	0.0587 (4)
H12A	−0.1604	0.4412	0.1068	0.070*
C12B	0.5284 (2)	0.03318 (14)	−0.20013 (12)	0.0595 (4)
H12B	0.4834	0.0704	−0.2526	0.071*
C13A	−0.0485 (2)	0.41730 (13)	0.24934 (11)	0.0575 (4)
H13A	−0.1118	0.3416	0.2374	0.069*
C13B	0.6654 (2)	0.09324 (13)	−0.11637 (12)	0.0582 (4)
H13B	0.7134	0.1709	−0.1127	0.070*
C14A	−0.0144 (2)	0.65174 (15)	0.10526 (13)	0.0638 (4)
C14B	0.3157 (2)	−0.14810 (14)	−0.29808 (13)	0.0587 (4)
H1NA	0.021 (2)	0.3362 (16)	0.4094 (14)	0.077 (5)*
H1NB	0.934 (2)	0.1706 (16)	0.0406 (13)	0.072 (5)*
H1OA	0.397 (3)	0.559 (2)	0.5941 (17)	0.103 (7)*
H1OB	0.886 (3)	−0.0526 (18)	0.2020 (16)	0.090 (7)*

	U11	U22	U33	U12	U13	U23
O1A	0.0813 (8)	0.0629 (7)	0.0783 (8)	−0.0142 (6)	−0.0038 (7)	0.0360 (6)
O1B	0.0827 (8)	0.0657 (7)	0.0713 (7)	−0.0186 (6)	0.0021 (6)	0.0304 (6)
N1A	0.0542 (7)	0.0505 (6)	0.0489 (6)	0.0056 (5)	0.0068 (5)	0.0149 (5)
N1B	0.0551 (7)	0.0543 (7)	0.0490 (6)	0.0068 (5)	0.0130 (5)	0.0201 (5)
N2A	0.0620 (8)	0.0531 (7)	0.0537 (7)	−0.0011 (6)	−0.0009 (6)	0.0186 (6)
N2B	0.0639 (8)	0.0588 (7)	0.0542 (7)	−0.0017 (6)	0.0061 (6)	0.0255 (6)
N3A	0.0952 (11)	0.0772 (10)	0.0642 (8)	−0.0075 (8)	0.0078 (8)	0.0344 (8)
N3B	0.0674 (9)	0.0678 (9)	0.0666 (8)	−0.0049 (7)	0.0042 (7)	0.0149 (7)
C1A	0.0532 (8)	0.0452 (7)	0.0546 (8)	0.0044 (6)	0.0127 (6)	0.0150 (6)
C1B	0.0511 (7)	0.0469 (7)	0.0535 (7)	0.0052 (6)	0.0171 (6)	0.0170 (6)
C2A	0.0508 (7)	0.0456 (7)	0.0499 (7)	0.0109 (6)	0.0147 (6)	0.0154 (6)
C2B	0.0489 (7)	0.0467 (7)	0.0487 (7)	0.0097 (6)	0.0160 (6)	0.0131 (6)
C3A	0.0546 (8)	0.0493 (7)	0.0563 (8)	0.0079 (6)	0.0107 (6)	0.0190 (6)
C3B	0.0598 (8)	0.0494 (8)	0.0547 (8)	0.0055 (6)	0.0142 (7)	0.0165 (6)
C4A	0.0608 (9)	0.0606 (9)	0.0655 (10)	0.0049 (7)	0.0017 (7)	0.0142 (8)
C4B	0.0817 (11)	0.0636 (10)	0.0624 (9)	0.0119 (8)	0.0186 (8)	0.0291 (8)
C5A	0.0726 (11)	0.0796 (11)	0.0534 (9)	0.0201 (9)	0.0019 (8)	0.0198 (8)
C5B	0.0836 (12)	0.0823 (12)	0.0557 (9)	0.0239 (10)	0.0102 (8)	0.0265 (9)
C6A	0.0845 (12)	0.0761 (11)	0.0603 (9)	0.0232 (9)	0.0188 (8)	0.0351 (8)
C6B	0.0619 (9)	0.0756 (11)	0.0581 (9)	0.0098 (8)	0.0015 (7)	0.0103 (8)
C7A	0.0683 (9)	0.0538 (8)	0.0617 (9)	0.0086 (7)	0.0180 (7)	0.0242 (7)
C7B	0.0532 (8)	0.0548 (8)	0.0602 (8)	0.0051 (6)	0.0139 (7)	0.0116 (7)
C8A	0.0539 (8)	0.0500 (7)	0.0495 (7)	0.0119 (6)	0.0120 (6)	0.0150 (6)
C8B	0.0521 (8)	0.0523 (8)	0.0488 (7)	0.0081 (6)	0.0152 (6)	0.0151 (6)
C9A	0.0634 (9)	0.0555 (8)	0.0499 (8)	0.0006 (7)	0.0058 (7)	0.0140 (6)
C9B	0.0594 (8)	0.0542 (8)	0.0547 (8)	0.0100 (6)	0.0156 (7)	0.0226 (6)
C10A	0.0691 (10)	0.0536 (8)	0.0599 (9)	−0.0006 (7)	0.0134 (7)	0.0180 (7)
C10B	0.0604 (9)	0.0495 (8)	0.0625 (9)	0.0053 (6)	0.0192 (7)	0.0173 (7)
C11A	0.0605 (9)	0.0572 (8)	0.0527 (8)	0.0104 (7)	0.0152 (7)	0.0211 (7)
C11B	0.0520 (8)	0.0563 (8)	0.0518 (8)	0.0065 (6)	0.0147 (6)	0.0128 (6)
C12A	0.0597 (9)	0.0593 (9)	0.0510 (8)	0.0072 (7)	0.0049 (7)	0.0160 (7)
C12B	0.0637 (9)	0.0586 (9)	0.0551 (8)	0.0080 (7)	0.0093 (7)	0.0226 (7)
C13A	0.0608 (9)	0.0486 (8)	0.0558 (8)	0.0032 (6)	0.0058 (7)	0.0140 (6)
C13B	0.0629 (9)	0.0515 (8)	0.0578 (8)	0.0025 (7)	0.0094 (7)	0.0218 (7)
C14A	0.0679 (10)	0.0624 (9)	0.0581 (9)	0.0013 (7)	0.0112 (7)	0.0219 (7)
C14B	0.0591 (9)	0.0559 (8)	0.0608 (9)	0.0058 (7)	0.0169 (7)	0.0171 (7)

O1A—C3A	1.3559 (17)	C5B—C6B	1.377 (3)
O1A—H1OA	0.98 (2)	C5B—H5B	0.9300
O1B—C3B	1.3520 (18)	C6A—C7A	1.376 (2)
O1B—H1OB	0.90 (2)	C6A—H6A	0.9300
N1A—C1A	1.2865 (17)	C6B—C7B	1.382 (2)
N1A—N2A	1.3597 (16)	C6B—H6B	0.9300
N1B—C1B	1.2801 (18)	C7A—H7A	0.9300
N1B—N2B	1.3674 (16)	C7B—H7B	0.9300
N2A—C8A	1.3734 (18)	C8A—C13A	1.3943 (19)
N2A—H1NA	0.914 (18)	C8A—C9A	1.399 (2)
N2B—C8B	1.3709 (18)	C8B—C13B	1.397 (2)
N2B—H1NB	0.894 (18)	C8B—C9B	1.4008 (19)
N3A—C14A	1.140 (2)	C9A—C10A	1.379 (2)
N3B—C14B	1.142 (2)	C9A—H9A	0.9300
C1A—C2A	1.4453 (19)	C9B—C10B	1.374 (2)
C1A—H1A	0.9300	C9B—H9B	0.9300
C1B—C2B	1.4517 (19)	C10A—C11A	1.387 (2)
C1B—H1B	0.9300	C10A—H10A	0.9300
C2A—C7A	1.3951 (19)	C10B—C11B	1.393 (2)
C2A—C3A	1.402 (2)	C10B—H10B	0.9300
C2B—C7B	1.3925 (19)	C11A—C12A	1.395 (2)
C2B—C3B	1.4017 (19)	C11A—C14A	1.439 (2)
C3A—C4A	1.383 (2)	C11B—C12B	1.394 (2)
C3B—C4B	1.391 (2)	C11B—C14B	1.432 (2)
C4A—C5A	1.373 (2)	C12A—C13A	1.370 (2)
C4A—H4A	0.9300	C12A—H12A	0.9300
C4B—C5B	1.367 (3)	C12B—C13B	1.363 (2)
C4B—H4B	0.9300	C12B—H12B	0.9300
C5A—C6A	1.378 (3)	C13A—H13A	0.9300
C5A—H5A	0.9300	C13B—H13B	0.9300
C3A—O1A—H1OA	106.5 (13)	C7B—C6B—H6B	120.4
C3B—O1B—H1OB	108.4 (13)	C6A—C7A—C2A	121.60 (15)
C1A—N1A—N2A	116.26 (12)	C6A—C7A—H7A	119.2
C1B—N1B—N2B	117.48 (12)	C2A—C7A—H7A	119.2
N1A—N2A—C8A	121.92 (12)	C6B—C7B—C2B	121.27 (15)
N1A—N2A—H1NA	119.3 (11)	C6B—C7B—H7B	119.4
C8A—N2A—H1NA	118.6 (11)	C2B—C7B—H7B	119.4
N1B—N2B—C8B	120.79 (12)	N2A—C8A—C13A	117.82 (13)
N1B—N2B—H1NB	117.9 (11)	N2A—C8A—C9A	123.00 (13)
C8B—N2B—H1NB	120.8 (11)	C13A—C8A—C9A	119.18 (13)
N1A—C1A—C2A	122.47 (13)	N2B—C8B—C13B	118.37 (13)
N1A—C1A—H1A	118.8	N2B—C8B—C9B	122.92 (13)
C2A—C1A—H1A	118.8	C13B—C8B—C9B	118.71 (13)
N1B—C1B—C2B	122.14 (12)	C10A—C9A—C8A	119.59 (14)
N1B—C1B—H1B	118.9	C10A—C9A—H9A	120.2
C2B—C1B—H1B	118.9	C8A—C9A—H9A	120.2
C7A—C2A—C3A	117.93 (13)	C10B—C9B—C8B	119.81 (13)
C7A—C2A—C1A	119.35 (13)	C10B—C9B—H9B	120.1
C3A—C2A—C1A	122.70 (13)	C8B—C9B—H9B	120.1
C7B—C2B—C3B	118.45 (13)	C9A—C10A—C11A	121.09 (14)
C7B—C2B—C1B	119.12 (13)	C9A—C10A—H10A	119.5
C3B—C2B—C1B	122.43 (13)	C11A—C10A—H10A	119.5
O1A—C3A—C4A	118.18 (14)	C9B—C10B—C11B	121.24 (13)
O1A—C3A—C2A	121.55 (13)	C9B—C10B—H10B	119.4
C4A—C3A—C2A	120.27 (14)	C11B—C10B—H10B	119.4
O1B—C3B—C4B	118.20 (14)	C10A—C11A—C12A	119.13 (13)
O1B—C3B—C2B	122.02 (13)	C10A—C11A—C14A	121.12 (14)
C4B—C3B—C2B	119.78 (15)	C12A—C11A—C14A	119.75 (14)
C5A—C4A—C3A	120.18 (16)	C10B—C11B—C12B	118.66 (14)
C5A—C4A—H4A	119.9	C10B—C11B—C14B	121.05 (14)
C3A—C4A—H4A	119.9	C12B—C11B—C14B	120.26 (14)
C5B—C4B—C3B	120.29 (16)	C13A—C12A—C11A	120.19 (14)
C5B—C4B—H4B	119.9	C13A—C12A—H12A	119.9
C3B—C4B—H4B	119.9	C11A—C12A—H12A	119.9
C4A—C5A—C6A	120.81 (15)	C13B—C12B—C11B	120.49 (14)
C4A—C5A—H5A	119.6	C13B—C12B—H12B	119.8
C6A—C5A—H5A	119.6	C11B—C12B—H12B	119.8
C4B—C5B—C6B	121.02 (15)	C12A—C13A—C8A	120.82 (14)
C4B—C5B—H5B	119.5	C12A—C13A—H13A	119.6
C6B—C5B—H5B	119.5	C8A—C13A—H13A	119.6
C7A—C6A—C5A	119.21 (15)	C12B—C13B—C8B	121.09 (14)
C7A—C6A—H6A	120.4	C12B—C13B—H13B	119.5
C5A—C6A—H6A	120.4	C8B—C13B—H13B	119.5
C5B—C6B—C7B	119.19 (16)	N3A—C14A—C11A	179.3 (2)
C5B—C6B—H6B	120.4	N3B—C14B—C11B	179.48 (19)
C13A—C8A—N2A—N1A	175.98 (13)	C13B—C8B—N2B—N1B	172.55 (13)
C8A—N2A—N1A—C1A	179.44 (14)	C8B—N2B—N1B—C1B	175.41 (13)
N2A—N1A—C1A—C2A	−179.93 (13)	N2B—N1B—C1B—C2B	177.44 (12)
N1A—C1A—C2A—C3A	0.2 (2)	N1B—C1B—C2B—C3B	−1.4 (2)
C1A—C2A—C3A—O1A	−1.3 (2)	C1B—C2B—C3B—O1B	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N1A	0.98 (2)	1.77 (2)	2.654 (2)	149 (2)
O1B—H1OB···N1B	0.90 (2)	1.86 (2)	2.653 (2)	147 (2)
N2A—H1NA···N3Bi	0.91 (2)	2.17 (2)	3.065 (2)	166 (2)
N2B—H1NB···N3Aii	0.89 (2)	2.25 (2)	3.098 (2)	158 (2)
C7A—H7A···O1Biii	0.93	2.55	3.427 (2)	156
C7B—H7B···O1Aiv	0.93	2.49	3.413 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯N1A	0.98 (2)	1.77 (2)	2.654 (2)	149 (2)
O1B—H1OB⋯N1B	0.90 (2)	1.86 (2)	2.653 (2)	147 (2)
N2A—H1NA⋯N3B i	0.91 (2)	2.17 (2)	3.065 (2)	166 (2)
N2B—H1NB⋯N3A ii	0.89 (2)	2.25 (2)	3.098 (2)	158 (2)
C7A—H7A⋯O1B iii	0.93	2.55	3.427 (2)	156
C7B—H7B⋯O1A iv	0.93	2.49	3.413 (2)	172

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .