(E)-4-Hy-droxy-N'-(2-meth-oxy-benzyl-idene)benzohydrazide.

In the title compound, C(15)H(14)N(2)O(3), the dihedral angle between the benzene rings is 66.56 (5)°. In the crystal, N-H⋯O, O-H⋯O and C-H⋯O inter-actions link the mol-ecules into a three-dimensional network. A π-π inter-action, with a centroid-centroid distance of 3.628 (6) Å, helps to establish the packing.

Related literature

For the properties of hydrazone derivatives, see: Lever (1972 ▶); Pelizzi & Pelizzi (1980 ▶). For related structures, see: Shan et al. (2003 ▶); Fun et al. (1996 ▶); Ferguson et al. (2005 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Orthorhombic,

a = 14.3951 (3) Å

b = 8.7449 (2) Å

c = 21.1047 (4) Å

V = 2656.74 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.49 × 0.28 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.991

32112 measured reflections

4442 independent reflections

3512 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.114

S = 1.03

4442 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021952/hb6791sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021952/hb6791Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021952/hb6791Isup3.cml

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

C15H14N2O3	F(000) = 1136
Mr = 270.28	Dx = 1.351 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8771 reflections
a = 14.3951 (3) Å	θ = 2.4–31.5°
b = 8.7449 (2) Å	µ = 0.10 mm−1
c = 21.1047 (4) Å	T = 100 K
V = 2656.74 (10) Å3	Plate, yellow
Z = 8	0.49 × 0.28 × 0.09 mm

Bruker SMART APEXII CCD diffractometer	4442 independent reflections
Radiation source: fine-focus sealed tube	3512 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 31.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
Tmin = 0.954, Tmax = 0.991	k = −12→12
32112 measured reflections	l = −30→31

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.959P] where P = (Fo2 + 2Fc2)/3
4442 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.48726 (6)	0.48027 (10)	0.36875 (4)	0.02079 (17)
O2	0.16105 (5)	0.45718 (9)	0.17195 (4)	0.01884 (16)
O3	0.13520 (6)	−0.20688 (9)	0.02729 (4)	0.02154 (18)
N1	0.22355 (7)	0.22544 (11)	0.14758 (4)	0.01752 (18)
N2	0.17102 (6)	0.21485 (11)	0.09246 (4)	0.01848 (19)
C1	0.38142 (7)	0.31733 (13)	0.22565 (5)	0.0181 (2)
H1A	0.3970	0.2544	0.1905	0.022*
C2	0.44845 (7)	0.35161 (13)	0.27091 (5)	0.0184 (2)
H2A	0.5098	0.3130	0.2665	0.022*
C3	0.42528 (7)	0.44303 (13)	0.32286 (5)	0.0170 (2)
C4	0.33481 (8)	0.49850 (14)	0.32950 (5)	0.0204 (2)
H4A	0.3185	0.5583	0.3654	0.024*
C5	0.26913 (7)	0.46623 (13)	0.28374 (5)	0.0187 (2)
H5A	0.2082	0.5066	0.2878	0.022*
C6	0.29126 (7)	0.37485 (12)	0.23154 (5)	0.01578 (19)
C7	0.21981 (7)	0.35457 (12)	0.18194 (5)	0.01583 (19)
C8	0.17442 (7)	0.08270 (13)	0.06597 (5)	0.0185 (2)
H8A	0.2048	0.0008	0.0871	0.022*
C9	0.13238 (7)	0.05622 (13)	0.00393 (5)	0.0176 (2)
C10	0.11156 (8)	0.17623 (13)	−0.03728 (5)	0.0210 (2)
H10A	0.1240	0.2785	−0.0246	0.025*
C11	0.07298 (8)	0.14849 (14)	−0.09648 (5)	0.0229 (2)
H11A	0.0582	0.2310	−0.1240	0.027*
C12	0.05632 (8)	−0.00132 (15)	−0.11500 (5)	0.0227 (2)
H12A	0.0301	−0.0208	−0.1555	0.027*
C13	0.07724 (8)	−0.12288 (14)	−0.07539 (5)	0.0209 (2)
H13A	0.0659	−0.2248	−0.0889	0.025*
C14	0.11498 (7)	−0.09490 (13)	−0.01561 (5)	0.0176 (2)
C15	0.11450 (9)	−0.36068 (13)	0.00934 (6)	0.0237 (2)
H15A	0.1294	−0.4297	0.0445	0.036*
H15B	0.1516	−0.3886	−0.0278	0.036*
H15C	0.0483	−0.3692	−0.0009	0.036*
H1N1	0.2628 (11)	0.1465 (19)	0.1575 (7)	0.027 (4)*
H1O1	0.5437 (14)	0.455 (2)	0.3577 (9)	0.050 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0171 (4)	0.0257 (4)	0.0195 (3)	−0.0008 (3)	−0.0020 (3)	−0.0037 (3)
O2	0.0166 (3)	0.0165 (4)	0.0233 (4)	0.0005 (3)	−0.0012 (3)	−0.0014 (3)
O3	0.0272 (4)	0.0151 (4)	0.0223 (4)	−0.0010 (3)	−0.0063 (3)	0.0006 (3)
N1	0.0184 (4)	0.0148 (4)	0.0194 (4)	−0.0003 (4)	−0.0037 (3)	−0.0015 (3)
N2	0.0178 (4)	0.0190 (4)	0.0187 (4)	−0.0013 (4)	−0.0023 (3)	−0.0012 (3)
C1	0.0176 (5)	0.0176 (5)	0.0192 (4)	−0.0007 (4)	0.0017 (3)	−0.0031 (4)
C2	0.0152 (4)	0.0187 (5)	0.0213 (4)	0.0012 (4)	0.0011 (3)	−0.0024 (4)
C3	0.0169 (4)	0.0167 (5)	0.0174 (4)	−0.0022 (4)	−0.0004 (3)	0.0007 (4)
C4	0.0199 (5)	0.0234 (5)	0.0178 (4)	0.0015 (5)	0.0011 (4)	−0.0039 (4)
C5	0.0169 (4)	0.0201 (5)	0.0191 (4)	0.0021 (4)	0.0010 (4)	−0.0018 (4)
C6	0.0158 (4)	0.0140 (4)	0.0175 (4)	−0.0009 (4)	0.0002 (3)	−0.0005 (4)
C7	0.0153 (4)	0.0146 (5)	0.0175 (4)	−0.0023 (4)	0.0021 (3)	−0.0003 (4)
C8	0.0185 (5)	0.0175 (5)	0.0196 (4)	−0.0014 (4)	−0.0022 (3)	0.0001 (4)
C9	0.0168 (4)	0.0180 (5)	0.0180 (4)	−0.0020 (4)	−0.0007 (3)	−0.0014 (4)
C10	0.0233 (5)	0.0169 (5)	0.0229 (5)	−0.0019 (4)	−0.0017 (4)	0.0007 (4)
C11	0.0258 (5)	0.0215 (5)	0.0213 (5)	−0.0004 (5)	−0.0023 (4)	0.0043 (4)
C12	0.0233 (5)	0.0261 (6)	0.0186 (4)	−0.0013 (5)	−0.0031 (4)	−0.0002 (4)
C13	0.0230 (5)	0.0195 (5)	0.0201 (4)	−0.0016 (5)	−0.0027 (4)	−0.0026 (4)
C14	0.0173 (4)	0.0172 (5)	0.0183 (4)	0.0000 (4)	−0.0008 (3)	−0.0001 (4)
C15	0.0288 (6)	0.0146 (5)	0.0278 (5)	−0.0019 (5)	−0.0038 (4)	−0.0006 (4)

O1—C3	1.3565 (12)	C5—H5A	0.9500
O1—H1O1	0.87 (2)	C6—C7	1.4782 (14)
O2—C7	1.2510 (13)	C8—C9	1.4609 (14)
O3—C14	1.3650 (13)	C8—H8A	0.9500
O3—C15	1.4287 (14)	C9—C10	1.3956 (15)
N1—C7	1.3432 (14)	C9—C14	1.4068 (16)
N1—N2	1.3905 (12)	C10—C11	1.3885 (15)
N1—H1N1	0.917 (16)	C10—H10A	0.9500
N2—C8	1.2848 (14)	C11—C12	1.3880 (17)
C1—C2	1.3904 (14)	C11—H11A	0.9500
C1—C6	1.3974 (15)	C12—C13	1.3856 (16)
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.3973 (15)	C13—C14	1.3953 (14)
C2—H2A	0.9500	C13—H13A	0.9500
C3—C4	1.3969 (15)	C15—H15A	0.9800
C4—C5	1.3806 (15)	C15—H15B	0.9800
C4—H4A	0.9500	C15—H15C	0.9800
C5—C6	1.3978 (14)
C3—O1—H1O1	111.1 (12)	N2—C8—C9	121.12 (10)
C14—O3—C15	117.06 (8)	N2—C8—H8A	119.4
C7—N1—N2	119.07 (9)	C9—C8—H8A	119.4
C7—N1—H1N1	122.3 (9)	C10—C9—C14	119.05 (10)
N2—N1—H1N1	118.5 (9)	C10—C9—C8	121.89 (10)
C8—N2—N1	113.78 (9)	C14—C9—C8	119.03 (10)
C2—C1—C6	120.38 (10)	C11—C10—C9	121.01 (11)
C2—C1—H1A	119.8	C11—C10—H10A	119.5
C6—C1—H1A	119.8	C9—C10—H10A	119.5
C1—C2—C3	119.79 (10)	C12—C11—C10	119.17 (10)
C1—C2—H2A	120.1	C12—C11—H11A	120.4
C3—C2—H2A	120.1	C10—C11—H11A	120.4
O1—C3—C4	117.28 (9)	C13—C12—C11	121.11 (10)
O1—C3—C2	122.73 (10)	C13—C12—H12A	119.4
C4—C3—C2	119.99 (10)	C11—C12—H12A	119.4
C5—C4—C3	119.82 (10)	C12—C13—C14	119.72 (11)
C5—C4—H4A	120.1	C12—C13—H13A	120.1
C3—C4—H4A	120.1	C14—C13—H13A	120.1
C4—C5—C6	120.81 (10)	O3—C14—C13	123.85 (10)
C4—C5—H5A	119.6	O3—C14—C9	116.20 (9)
C6—C5—H5A	119.6	C13—C14—C9	119.93 (10)
C1—C6—C5	119.18 (9)	O3—C15—H15A	109.5
C1—C6—C7	122.68 (9)	O3—C15—H15B	109.5
C5—C6—C7	117.92 (9)	H15A—C15—H15B	109.5
O2—C7—N1	122.63 (9)	O3—C15—H15C	109.5
O2—C7—C6	120.24 (9)	H15A—C15—H15C	109.5
N1—C7—C6	117.09 (9)	H15B—C15—H15C	109.5
C7—N1—N2—C8	−175.07 (10)	N1—N2—C8—C9	−172.79 (9)
C6—C1—C2—C3	0.55 (17)	N2—C8—C9—C10	19.20 (16)
C1—C2—C3—O1	179.77 (10)	N2—C8—C9—C14	−162.77 (10)
C1—C2—C3—C4	0.59 (17)	C14—C9—C10—C11	0.93 (17)
O1—C3—C4—C5	179.00 (10)	C8—C9—C10—C11	178.95 (10)
C2—C3—C4—C5	−1.77 (17)	C9—C10—C11—C12	−0.96 (18)
C3—C4—C5—C6	1.84 (17)	C10—C11—C12—C13	0.22 (18)
C2—C1—C6—C5	−0.50 (16)	C11—C12—C13—C14	0.54 (18)
C2—C1—C6—C7	173.99 (10)	C15—O3—C14—C13	−1.07 (16)
C4—C5—C6—C1	−0.70 (16)	C15—O3—C14—C9	177.53 (10)
C4—C5—C6—C7	−175.45 (10)	C12—C13—C14—O3	177.98 (10)
N2—N1—C7—O2	10.90 (15)	C12—C13—C14—C9	−0.57 (16)
N2—N1—C7—C6	−166.78 (9)	C10—C9—C14—O3	−178.81 (10)
C1—C6—C7—O2	−145.49 (11)	C8—C9—C14—O3	3.10 (14)
C5—C6—C7—O2	29.07 (15)	C10—C9—C14—C13	−0.15 (16)
C1—C6—C7—N1	32.25 (15)	C8—C9—C14—C13	−178.24 (10)
C5—C6—C7—N1	−153.19 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.916 (16)	2.009 (16)	2.9202 (12)	172.8 (15)
O1—H1O1···O2ii	0.87 (2)	1.80 (2)	2.6528 (11)	164.2 (17)
C13—H13A···O1iii	0.95	2.52	3.4669 (15)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.916 (16)	2.009 (16)	2.9202 (12)	172.8 (15)
O1—H1O1⋯O2ii	0.87 (2)	1.80 (2)	2.6528 (11)	164.2 (17)
C13—H13A⋯O1iii	0.95	2.52	3.4669 (15)	171

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