(E)-N'-(4-Hydroxy-benzyl-idene)-2-methoxy-benzohydrazide.

The title compound, C(15)H(14)N(2)O(3), exists in the E configuration with respect to the central methyl-idene unit. The dihedral angle between the two substituted benzene rings is 22.0 (2)°. Within the mol-ecule there is an intra-molecular N-H⋯O hydrogen bond involving the hydro-zide H atom and the O atom of the meth-oxy substituent on the adjacent phenyl ring. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds, forming zigzag chains along the b direction.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background on the biological properties of hydrazones, see: El-Tabl et al. (2008 ▶); Chen et al. (2008 ▶); Alvarez et al. (2008 ▶); Ventura & Martins (2008 ▶); Kalinowski et al. (2008 ▶). For related structures, see: Diao & Yu (2006 ▶); Shan et al. (2008 ▶); Fun et al. (2008 ▶); Yehye et al. (2008 ▶); Ejsmont et al. (2008 ▶); Han et al. (2006 ▶); Lu et al. (2008 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Orthorhombic,

a = 13.113 (3) Å

b = 9.189 (2) Å

c = 22.110 (4) Å

V = 2664.2 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.991, T max = 0.992

20705 measured reflections

2899 independent reflections

1656 reflections with I > 2σ(I)

R int = 0.084

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.136

S = 1.02

2899 reflections

186 parameters

1 restraint

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: 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/S1600536808029334/su2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029334/su2061Isup2.hkl

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

C15H14N2O3	F(000) = 1136
Mr = 270.28	Dx = 1.348 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1422 reflections
a = 13.113 (3) Å	θ = 2.4–24.5°
b = 9.189 (2) Å	µ = 0.10 mm−1
c = 22.110 (4) Å	T = 298 K
V = 2664.2 (10) Å3	Block, colourless
Z = 8	0.10 × 0.10 × 0.08 mm

Bruker SMART 1000 CCD area-detector diffractometer	2899 independent reflections
Radiation source: fine-focus sealed tube	1656 reflections with I > 2σ(I)
graphite	Rint = 0.084
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.991, Tmax = 0.992	k = −11→11
20705 measured reflections	l = −28→28

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.6248P] where P = (Fo2 + 2Fc2)/3
2899 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.15 e Å−3
1 restraint	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
O1	0.05041 (12)	0.41453 (19)	0.87757 (7)	0.0566 (5)
H1	−0.0077	0.4422	0.8850	0.085*
O2	0.12254 (12)	1.04261 (19)	0.58301 (7)	0.0603 (5)
O3	0.43319 (11)	1.01975 (19)	0.60152 (7)	0.0565 (5)
N1	0.18804 (13)	0.8432 (2)	0.66327 (8)	0.0445 (5)
N2	0.25132 (14)	0.9141 (2)	0.62338 (8)	0.0460 (5)
C1	0.18233 (16)	0.6684 (2)	0.74406 (10)	0.0423 (6)
C2	0.23796 (17)	0.5671 (3)	0.77706 (10)	0.0488 (6)
H2	0.3071	0.5555	0.7690	0.059*
C3	0.19308 (17)	0.4837 (3)	0.82142 (10)	0.0493 (6)
H3	0.2319	0.4168	0.8430	0.059*
C4	0.09138 (16)	0.4992 (2)	0.83370 (9)	0.0413 (6)
C5	0.03475 (17)	0.5996 (3)	0.80141 (11)	0.0537 (7)
H5	−0.0343	0.6112	0.8097	0.064*
C6	0.07971 (17)	0.6823 (3)	0.75726 (10)	0.0527 (7)
H6	0.0405	0.7489	0.7358	0.063*
C7	0.23330 (17)	0.7529 (3)	0.69767 (10)	0.0467 (6)
H7	0.3032	0.7404	0.6928	0.056*
C8	0.21358 (17)	1.0145 (2)	0.58522 (9)	0.0415 (5)
C9	0.28755 (16)	1.0927 (2)	0.54622 (9)	0.0409 (5)
C10	0.39297 (17)	1.1018 (3)	0.55572 (10)	0.0440 (6)
C11	0.4525 (2)	1.1908 (3)	0.51948 (11)	0.0585 (7)
H11	0.5224	1.1971	0.5263	0.070*
C12	0.4087 (2)	1.2695 (3)	0.47368 (12)	0.0667 (8)
H12	0.4489	1.3305	0.4501	0.080*
C13	0.3060 (2)	1.2592 (3)	0.46224 (12)	0.0642 (7)
H13	0.2769	1.3110	0.4305	0.077*
C14	0.24661 (19)	1.1715 (3)	0.49838 (10)	0.0532 (6)
H14	0.1771	1.1647	0.4905	0.064*
C15	0.53806 (18)	1.0379 (3)	0.61787 (12)	0.0671 (8)
H15A	0.5805	1.0137	0.5840	0.101*
H15B	0.5540	0.9750	0.6512	0.101*
H15C	0.5499	1.1372	0.6294	0.101*
H2A	0.3188 (8)	0.900 (3)	0.6214 (12)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0478 (10)	0.0620 (11)	0.0600 (10)	0.0031 (9)	0.0133 (8)	0.0151 (9)
O2	0.0392 (10)	0.0760 (13)	0.0656 (11)	0.0092 (9)	0.0079 (8)	0.0192 (10)
O3	0.0400 (9)	0.0684 (12)	0.0611 (10)	−0.0044 (8)	−0.0049 (8)	0.0097 (9)
N1	0.0417 (11)	0.0500 (12)	0.0419 (10)	−0.0011 (9)	0.0048 (9)	0.0008 (10)
N2	0.0366 (10)	0.0537 (13)	0.0477 (11)	0.0013 (10)	0.0096 (9)	0.0093 (10)
C1	0.0372 (12)	0.0498 (14)	0.0400 (12)	0.0021 (11)	0.0026 (10)	−0.0010 (11)
C2	0.0329 (12)	0.0626 (17)	0.0509 (14)	0.0050 (11)	0.0069 (10)	0.0057 (13)
C3	0.0444 (14)	0.0528 (16)	0.0508 (14)	0.0087 (12)	0.0029 (11)	0.0081 (12)
C4	0.0412 (13)	0.0441 (14)	0.0386 (12)	−0.0025 (11)	0.0044 (10)	−0.0017 (11)
C5	0.0340 (12)	0.0695 (18)	0.0575 (15)	0.0055 (12)	0.0067 (11)	0.0122 (13)
C6	0.0430 (14)	0.0646 (18)	0.0506 (14)	0.0104 (12)	0.0004 (11)	0.0132 (13)
C7	0.0394 (13)	0.0546 (16)	0.0460 (13)	0.0040 (12)	0.0080 (10)	0.0026 (12)
C8	0.0407 (13)	0.0460 (14)	0.0377 (12)	0.0023 (11)	0.0025 (10)	−0.0014 (11)
C9	0.0436 (13)	0.0385 (13)	0.0407 (12)	0.0015 (11)	0.0049 (10)	−0.0015 (11)
C10	0.0482 (14)	0.0440 (14)	0.0399 (12)	−0.0019 (11)	0.0030 (10)	−0.0025 (11)
C11	0.0566 (16)	0.0604 (18)	0.0584 (16)	−0.0162 (13)	0.0065 (13)	−0.0018 (14)
C12	0.083 (2)	0.0601 (18)	0.0573 (16)	−0.0179 (16)	0.0138 (15)	0.0089 (15)
C13	0.082 (2)	0.0573 (18)	0.0537 (15)	0.0071 (16)	0.0087 (14)	0.0144 (14)
C14	0.0518 (14)	0.0564 (17)	0.0514 (14)	0.0062 (13)	0.0036 (12)	0.0038 (13)
C15	0.0461 (15)	0.076 (2)	0.0793 (19)	−0.0062 (14)	−0.0128 (14)	−0.0078 (16)

O1—C4	1.355 (2)	C5—H5	0.9300
O1—H1	0.8200	C6—H6	0.9300
O2—C8	1.222 (3)	C7—H7	0.9300
O3—C10	1.368 (3)	C8—C9	1.484 (3)
O3—C15	1.432 (3)	C9—C14	1.389 (3)
N1—C7	1.272 (3)	C9—C10	1.401 (3)
N1—N2	1.375 (2)	C10—C11	1.386 (3)
N2—C8	1.344 (3)	C11—C12	1.371 (4)
N2—H2A	0.895 (10)	C11—H11	0.9300
C1—C6	1.383 (3)	C12—C13	1.373 (4)
C1—C2	1.389 (3)	C12—H12	0.9300
C1—C7	1.450 (3)	C13—C14	1.377 (3)
C2—C3	1.377 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.368 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.383 (3)	C15—H15C	0.9600
C5—C6	1.370 (3)
C4—O1—H1	109.5	O2—C8—N2	122.0 (2)
C10—O3—C15	119.53 (19)	O2—C8—C9	120.8 (2)
C7—N1—N2	114.27 (18)	N2—C8—C9	117.2 (2)
C8—N2—N1	120.36 (19)	C14—C9—C10	117.7 (2)
C8—N2—H2A	115.6 (18)	C14—C9—C8	116.2 (2)
N1—N2—H2A	124.1 (18)	C10—C9—C8	125.9 (2)
C6—C1—C2	117.5 (2)	O3—C10—C11	122.4 (2)
C6—C1—C7	123.3 (2)	O3—C10—C9	117.3 (2)
C2—C1—C7	119.2 (2)	C11—C10—C9	120.3 (2)
C3—C2—C1	121.5 (2)	C12—C11—C10	120.1 (3)
C3—C2—H2	119.2	C12—C11—H11	119.9
C1—C2—H2	119.2	C10—C11—H11	119.9
C4—C3—C2	120.0 (2)	C11—C12—C13	120.8 (3)
C4—C3—H3	120.0	C11—C12—H12	119.6
C2—C3—H3	120.0	C13—C12—H12	119.6
O1—C4—C3	118.0 (2)	C12—C13—C14	119.2 (3)
O1—C4—C5	122.7 (2)	C12—C13—H13	120.4
C3—C4—C5	119.4 (2)	C14—C13—H13	120.4
C6—C5—C4	120.4 (2)	C13—C14—C9	121.9 (2)
C6—C5—H5	119.8	C13—C14—H14	119.0
C4—C5—H5	119.8	C9—C14—H14	119.0
C5—C6—C1	121.2 (2)	O3—C15—H15A	109.5
C5—C6—H6	119.4	O3—C15—H15B	109.5
C1—C6—H6	119.4	H15A—C15—H15B	109.5
N1—C7—C1	123.9 (2)	O3—C15—H15C	109.5
N1—C7—H7	118.1	H15A—C15—H15C	109.5
C1—C7—H7	118.1	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.90 (1)	1.91 (2)	2.620 (2)	135 (2)
O1—H1···O2i	0.82	1.90	2.700 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.895 (10)	1.91 (2)	2.620 (2)	135 (2)
O1—H1⋯O2i	0.82	1.90	2.700 (2)	164

Symmetry code: (i) .