3-Hydr-oxy-N'-(2-hydroxy-benzyl-idene)benzohydrazide.

The title compound, C(14)H(12)N(2)O(3), was synthesized by the condensation of salicylaldehyde with 3-hydroxy-benzo-hydrazide. The dihedral angle between the two benzene rings is 12.4 (2)°. The 2-hydr-oxy group forms an intra-molecular O-H⋯N hydrogen bond with the imide N atom. Mol-ecules are linked through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds into a two-dimensional polymeric structure parallel to the ab plane.

Related literature

For related literature, see: Ali et al. (2005 ▶); Eltayeb et al. (2008 ▶); Habibi et al. (2007 ▶); Jing et al. (2006 ▶); Ling et al. (2008 ▶); Peng & You (2007 ▶); Peng & Zhou (2007 ▶); Peng, Ping & Song (2007 ▶); Peng, Yang & Zhou (2006 ▶); Peng, Zhou & Yang (2006 ▶); Yehye et al. (2008 ▶).

Experimental

Crystal data

C14H12N2O3

M = 256.26

Orthorhombic,

a = 14.405 (2) Å

b = 9.661 (1) Å

c = 17.905 (2) Å

V = 2491.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.978, T max = 0.981

13415 measured reflections

2720 independent reflections

1869 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.03

2720 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027426/gk2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027426/gk2164Isup2.hkl

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

C14H12N2O3	F(000) = 1072
Mr = 256.26	Dx = 1.366 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3092 reflections
a = 14.405 (2) Å	θ = 2.7–26.0°
b = 9.661 (1) Å	µ = 0.10 mm−1
c = 17.905 (2) Å	T = 298 K
V = 2491.8 (5) Å3	Block, colorless
Z = 8	0.23 × 0.20 × 0.20 mm

Bruker SMART 1000 CCD area-detector diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→18
Tmin = 0.978, Tmax = 0.981	k = −11→12
13415 measured reflections	l = −22→22

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3997P] where P = (Fo2 + 2Fc2)/3
2720 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.18 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
O1	0.16163 (8)	1.20579 (14)	0.04590 (8)	0.0677 (4)
H1	0.1829	1.1427	0.0713	0.102*
O2	0.33625 (7)	0.98665 (12)	0.15618 (6)	0.0524 (3)
O3	0.56381 (7)	0.66767 (12)	0.27314 (7)	0.0548 (3)
H3	0.5826	0.6036	0.2991	0.082*
N1	0.15527 (8)	0.98711 (13)	0.13048 (7)	0.0419 (3)
N2	0.19669 (8)	0.88568 (13)	0.17276 (8)	0.0436 (3)
C1	0.01929 (10)	1.09152 (16)	0.08195 (8)	0.0409 (4)
C2	0.06764 (12)	1.19810 (18)	0.04586 (9)	0.0493 (4)
C3	0.01833 (15)	1.3000 (2)	0.00834 (11)	0.0668 (5)
H3A	0.0501	1.3716	−0.0152	0.080*
C4	−0.07686 (16)	1.2964 (2)	0.00557 (11)	0.0709 (6)
H4	−0.1089	1.3653	−0.0200	0.085*
C5	−0.12534 (13)	1.1922 (2)	0.04022 (11)	0.0663 (6)
H5	−0.1898	1.1900	0.0380	0.080*
C6	−0.07735 (11)	1.0909 (2)	0.07839 (9)	0.0533 (4)
H6	−0.1102	1.0207	0.1022	0.064*
C7	0.06694 (10)	0.98419 (16)	0.12381 (9)	0.0423 (4)
H7	0.0331	0.9131	0.1458	0.051*
C8	0.28882 (10)	0.89504 (16)	0.18561 (8)	0.0411 (4)
C9	0.32990 (9)	0.78911 (16)	0.23665 (9)	0.0396 (4)
C10	0.42602 (10)	0.77388 (16)	0.23447 (9)	0.0402 (4)
H10	0.4612	0.8302	0.2033	0.048*
C11	0.46926 (9)	0.67575 (16)	0.27832 (9)	0.0407 (4)
C12	0.41777 (11)	0.59119 (18)	0.32492 (9)	0.0474 (4)
H12	0.4468	0.5240	0.3538	0.057*
C13	0.32267 (11)	0.6079 (2)	0.32798 (10)	0.0561 (5)
H13	0.2878	0.5519	0.3596	0.067*
C14	0.27860 (11)	0.70631 (19)	0.28484 (9)	0.0517 (4)
H14	0.2146	0.7172	0.2880	0.062*
H2	0.1622 (12)	0.8175 (16)	0.1921 (11)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0516 (7)	0.0702 (10)	0.0815 (10)	−0.0133 (6)	0.0067 (6)	0.0162 (7)
O2	0.0375 (6)	0.0518 (7)	0.0680 (8)	−0.0079 (5)	−0.0066 (5)	0.0050 (6)
O3	0.0286 (5)	0.0524 (7)	0.0835 (9)	0.0054 (5)	−0.0026 (5)	0.0072 (6)
N1	0.0331 (6)	0.0436 (8)	0.0488 (7)	0.0030 (5)	−0.0044 (5)	−0.0028 (6)
N2	0.0297 (6)	0.0423 (8)	0.0586 (8)	0.0007 (5)	−0.0060 (6)	0.0025 (6)
C1	0.0378 (8)	0.0462 (9)	0.0387 (8)	0.0039 (7)	−0.0007 (6)	−0.0018 (7)
C2	0.0507 (10)	0.0523 (10)	0.0448 (9)	−0.0009 (8)	0.0011 (7)	−0.0004 (8)
C3	0.0846 (15)	0.0592 (12)	0.0566 (11)	0.0036 (10)	0.0013 (10)	0.0144 (9)
C4	0.0794 (14)	0.0749 (14)	0.0583 (12)	0.0259 (11)	−0.0111 (11)	0.0105 (10)
C5	0.0491 (10)	0.0885 (15)	0.0614 (12)	0.0206 (10)	−0.0073 (9)	0.0031 (11)
C6	0.0401 (9)	0.0672 (12)	0.0525 (10)	0.0064 (8)	−0.0014 (7)	0.0054 (9)
C7	0.0359 (8)	0.0434 (9)	0.0476 (9)	−0.0005 (6)	0.0000 (7)	0.0001 (7)
C8	0.0312 (7)	0.0424 (9)	0.0497 (9)	−0.0003 (7)	−0.0027 (6)	−0.0081 (7)
C9	0.0286 (7)	0.0440 (9)	0.0461 (8)	−0.0005 (6)	−0.0040 (6)	−0.0075 (7)
C10	0.0296 (7)	0.0395 (8)	0.0516 (9)	−0.0022 (6)	0.0002 (6)	−0.0050 (7)
C11	0.0275 (7)	0.0417 (8)	0.0529 (9)	0.0026 (6)	−0.0050 (7)	−0.0113 (7)
C12	0.0414 (8)	0.0540 (10)	0.0467 (9)	0.0054 (7)	−0.0046 (7)	0.0004 (8)
C13	0.0394 (9)	0.0740 (13)	0.0548 (10)	−0.0012 (8)	0.0048 (7)	0.0130 (9)
C14	0.0282 (7)	0.0729 (12)	0.0541 (10)	0.0016 (7)	0.0006 (7)	0.0026 (9)

O1—C2	1.356 (2)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.380 (3)
O2—C8	1.2360 (18)	C5—H5	0.9300
O3—C11	1.3673 (17)	C6—H6	0.9300
O3—H3	0.8200	C7—H7	0.9300
N1—C7	1.2784 (18)	C8—C9	1.494 (2)
N1—N2	1.3745 (18)	C9—C14	1.389 (2)
N2—C8	1.3499 (18)	C9—C10	1.3928 (19)
N2—H2	0.895 (9)	C10—C11	1.379 (2)
C1—C6	1.394 (2)	C10—H10	0.9300
C1—C2	1.401 (2)	C11—C12	1.383 (2)
C1—C7	1.452 (2)	C12—C13	1.380 (2)
C2—C3	1.388 (2)	C12—H12	0.9300
C3—C4	1.373 (3)	C13—C14	1.380 (2)
C3—H3A	0.9300	C13—H13	0.9300
C4—C5	1.373 (3)	C14—H14	0.9300
C2—O1—H1	109.5	N1—C7—C1	120.20 (14)
C11—O3—H3	109.5	N1—C7—H7	119.9
C7—N1—N2	117.88 (13)	C1—C7—H7	119.9
C8—N2—N1	118.21 (13)	O2—C8—N2	121.25 (14)
C8—N2—H2	122.0 (13)	O2—C8—C9	122.15 (13)
N1—N2—H2	119.8 (13)	N2—C8—C9	116.60 (13)
C6—C1—C2	118.60 (15)	C14—C9—C10	119.03 (14)
C6—C1—C7	119.53 (15)	C14—C9—C8	124.29 (13)
C2—C1—C7	121.86 (14)	C10—C9—C8	116.68 (13)
O1—C2—C3	118.19 (16)	C11—C10—C9	120.37 (14)
O1—C2—C1	122.45 (15)	C11—C10—H10	119.8
C3—C2—C1	119.36 (17)	C9—C10—H10	119.8
C4—C3—C2	120.71 (19)	O3—C11—C10	116.77 (14)
C4—C3—H3A	119.6	O3—C11—C12	122.77 (14)
C2—C3—H3A	119.6	C10—C11—C12	120.46 (13)
C3—C4—C5	120.68 (18)	C13—C12—C11	119.15 (15)
C3—C4—H4	119.7	C13—C12—H12	120.4
C5—C4—H4	119.7	C11—C12—H12	120.4
C4—C5—C6	119.29 (18)	C14—C13—C12	120.98 (16)
C4—C5—H5	120.4	C14—C13—H13	119.5
C6—C5—H5	120.4	C12—C13—H13	119.5
C5—C6—C1	121.34 (18)	C13—C14—C9	119.98 (14)
C5—C6—H6	119.3	C13—C14—H14	120.0
C1—C6—H6	119.3	C9—C14—H14	120.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.6010 (19)	146.
O3—H3···O2i	0.82	1.81	2.5946 (16)	159.
N2—H2···O3ii	0.90 (1)	2.12 (1)	3.0062 (18)	171.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.6010 (19)	146
O3—H3⋯O2i	0.82	1.81	2.5946 (16)	159
N2—H2⋯O3ii	0.895 (9)	2.119 (10)	3.0062 (18)	171.0 (18)

Symmetry codes: (i) ; (ii) .