(E)-4-Hy-droxy-N'-(3-hy-droxy-4-meth-oxy-benzyl-idene)benzohydrazide.

The mol-ecule of the title benzohydrazide derivative, C(15)H(14)N(2)O(4), exists in a trans conformation with respect to the C=N double bond and is twisted, the dihedral angle between the two benzene rings being 24.17 (6)°. The meth-oxy group is almost co-planar with respect to the attached benzene ring [C(m)-O-C-C (m = meth-yl) = -1.45 (17)°]. In the crystal, the mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds into sheets parallel to the bc plane. These sheets are further connected into a three-dimensional network by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Li & Ban (2009 ▶); Zhang (2011 ▶). For background to and applications of benzohydrazide derivatives, see: Bedia et al. (2006 ▶); Bhole & Bhusari (2009 ▶); Loncle et al. (2004 ▶); Raj et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Monoclinic,

a = 10.7484 (5) Å

b = 9.4669 (4) Å

c = 15.7198 (5) Å

β = 122.166 (2)°

V = 1354.04 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.42 × 0.29 × 0.19 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.958, T max = 0.981

16525 measured reflections

3910 independent reflections

3438 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.125

S = 1.03

3910 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.49 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) global, I. DOI: 10.1107/S1600536811036579/hb6400sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036579/hb6400Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036579/hb6400Isup3.cml

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

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.404 Mg m−3
Monoclinic, P21/c	Melting point = 516 (decompose)–516 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.7484 (5) Å	Cell parameters from 3910 reflections
b = 9.4669 (4) Å	θ = 2.2–30.0°
c = 15.7198 (5) Å	µ = 0.10 mm−1
β = 122.166 (2)°	T = 100 K
V = 1354.04 (10) Å3	Block, colorless
Z = 4	0.42 × 0.29 × 0.19 mm

Bruker APEX DUO CCD diffractometer	3910 independent reflections
Radiation source: sealed tube	3438 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→15
Tmin = 0.958, Tmax = 0.981	k = −13→13
16525 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0719P)2 + 0.4766P] where P = (Fo2 + 2Fc2)/3
3910 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.49 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.43925 (8)	1.18018 (8)	0.58385 (5)	0.01852 (17)
O2	0.49471 (9)	1.47445 (8)	0.24675 (6)	0.01967 (17)
H2A	0.4792	1.4316	0.1952	0.030*
O3	0.26685 (8)	0.66939 (8)	0.80751 (6)	0.01987 (17)
H3A	0.3556	0.6774	0.8260	0.030*
O4	0.01675 (9)	0.54612 (9)	0.72204 (6)	0.02306 (18)
N1	0.28428 (10)	1.03431 (9)	0.45801 (6)	0.01717 (18)
H1A	0.2380	1.0104	0.3942	0.021*
N2	0.26221 (9)	0.96119 (9)	0.52515 (6)	0.01676 (18)
C1	0.40755 (10)	1.22076 (10)	0.42422 (7)	0.01464 (18)
C2	0.50952 (12)	1.33110 (12)	0.46469 (8)	0.0208 (2)
H2B	0.5603	1.3494	0.5348	0.025*
C3	0.53774 (12)	1.41401 (12)	0.40453 (8)	0.0229 (2)
H3B	0.6071	1.4888	0.4334	0.027*
C4	0.46467 (10)	1.38813 (10)	0.30166 (7)	0.01553 (19)
C5	0.36654 (12)	1.27532 (12)	0.26061 (8)	0.0210 (2)
H5A	0.3193	1.2547	0.1910	0.025*
C6	0.33780 (12)	1.19320 (12)	0.32125 (8)	0.0208 (2)
H6A	0.2699	1.1173	0.2925	0.025*
C7	0.37956 (10)	1.14385 (10)	0.49418 (7)	0.01477 (18)
C8	0.15580 (12)	0.87261 (12)	0.48512 (8)	0.0204 (2)
H8A	0.0982	0.8631	0.4141	0.024*
C9	0.12146 (11)	0.78585 (11)	0.54692 (8)	0.0189 (2)
C10	0.21899 (10)	0.77112 (10)	0.65114 (7)	0.01542 (19)
H10A	0.3115	0.8176	0.6838	0.019*
C11	0.18034 (10)	0.68906 (10)	0.70614 (7)	0.01506 (19)
C12	0.04194 (11)	0.62256 (11)	0.65889 (8)	0.0189 (2)
C13	−0.05414 (13)	0.63664 (15)	0.55581 (9)	0.0306 (3)
H13A	−0.1475	0.5918	0.5232	0.037*
C14	−0.01309 (13)	0.71667 (15)	0.50042 (9)	0.0312 (3)
H14A	−0.0781	0.7241	0.4297	0.037*
C15	−0.12259 (13)	0.47708 (14)	0.67802 (10)	0.0297 (3)
H15D	−0.1294	0.4289	0.7306	0.045*
H15A	−0.1325	0.4077	0.6285	0.045*
H15B	−0.2014	0.5473	0.6448	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (3)	0.0232 (4)	0.0119 (3)	−0.0039 (3)	0.0090 (3)	−0.0025 (3)
O2	0.0247 (4)	0.0215 (4)	0.0148 (3)	−0.0043 (3)	0.0119 (3)	0.0004 (3)
O3	0.0180 (3)	0.0263 (4)	0.0132 (3)	−0.0006 (3)	0.0069 (3)	0.0032 (3)
O4	0.0221 (4)	0.0259 (4)	0.0225 (4)	−0.0044 (3)	0.0128 (3)	0.0058 (3)
N1	0.0221 (4)	0.0188 (4)	0.0119 (4)	−0.0044 (3)	0.0100 (3)	−0.0008 (3)
N2	0.0198 (4)	0.0186 (4)	0.0146 (4)	0.0001 (3)	0.0110 (3)	0.0020 (3)
C1	0.0162 (4)	0.0159 (4)	0.0129 (4)	−0.0002 (3)	0.0085 (3)	−0.0002 (3)
C2	0.0222 (5)	0.0248 (5)	0.0121 (4)	−0.0074 (4)	0.0069 (4)	−0.0013 (4)
C3	0.0244 (5)	0.0265 (5)	0.0142 (5)	−0.0107 (4)	0.0079 (4)	−0.0018 (4)
C4	0.0170 (4)	0.0172 (4)	0.0142 (4)	0.0007 (3)	0.0096 (3)	0.0014 (3)
C5	0.0263 (5)	0.0244 (5)	0.0131 (4)	−0.0077 (4)	0.0111 (4)	−0.0040 (4)
C6	0.0265 (5)	0.0221 (5)	0.0155 (5)	−0.0097 (4)	0.0124 (4)	−0.0055 (4)
C7	0.0158 (4)	0.0163 (4)	0.0130 (4)	0.0009 (3)	0.0081 (3)	0.0004 (3)
C8	0.0211 (5)	0.0246 (5)	0.0141 (4)	−0.0031 (4)	0.0084 (4)	0.0021 (4)
C9	0.0184 (4)	0.0219 (5)	0.0153 (4)	−0.0030 (3)	0.0083 (4)	0.0023 (3)
C10	0.0146 (4)	0.0165 (4)	0.0154 (4)	−0.0009 (3)	0.0081 (3)	−0.0003 (3)
C11	0.0155 (4)	0.0156 (4)	0.0137 (4)	0.0017 (3)	0.0076 (3)	0.0006 (3)
C12	0.0189 (4)	0.0199 (5)	0.0189 (5)	−0.0023 (3)	0.0106 (4)	0.0030 (4)
C13	0.0200 (5)	0.0428 (7)	0.0205 (5)	−0.0137 (5)	0.0050 (4)	0.0054 (5)
C14	0.0225 (5)	0.0452 (7)	0.0158 (5)	−0.0128 (5)	0.0032 (4)	0.0066 (5)
C15	0.0267 (5)	0.0295 (6)	0.0348 (6)	−0.0092 (4)	0.0177 (5)	0.0038 (5)

O1—C7	1.2465 (12)	C4—C5	1.3946 (14)
O2—C4	1.3468 (12)	C5—C6	1.3864 (14)
O2—H2A	0.8400	C5—H5A	0.9500
O3—C11	1.3642 (12)	C6—H6A	0.9500
O3—H3A	0.8400	C8—C9	1.4616 (14)
O4—C12	1.3671 (12)	C8—H8A	0.9500
O4—C15	1.4302 (13)	C9—C14	1.3889 (15)
N1—C7	1.3518 (13)	C9—C10	1.4049 (13)
N1—N2	1.3841 (11)	C10—C11	1.3804 (13)
N1—H1A	0.8800	C10—H10A	0.9500
N2—C8	1.2811 (13)	C11—C12	1.4087 (14)
C1—C2	1.3981 (13)	C12—C13	1.3886 (15)
C1—C6	1.3992 (13)	C13—C14	1.3913 (16)
C1—C7	1.4774 (13)	C13—H13A	0.9500
C2—C3	1.3813 (14)	C14—H14A	0.9500
C2—H2B	0.9500	C15—H15D	0.9800
C3—C4	1.3927 (14)	C15—H15A	0.9800
C3—H3B	0.9500	C15—H15B	0.9800
C4—O2—H2A	109.5	N2—C8—C9	121.12 (9)
C11—O3—H3A	109.5	N2—C8—H8A	119.4
C12—O4—C15	116.86 (9)	C9—C8—H8A	119.4
C7—N1—N2	117.51 (8)	C14—C9—C10	119.23 (10)
C7—N1—H1A	121.2	C14—C9—C8	118.41 (9)
N2—N1—H1A	121.2	C10—C9—C8	122.36 (9)
C8—N2—N1	115.06 (8)	C11—C10—C9	119.98 (9)
C2—C1—C6	118.24 (9)	C11—C10—H10A	120.0
C2—C1—C7	116.77 (9)	C9—C10—H10A	120.0
C6—C1—C7	124.97 (9)	O3—C11—C10	124.27 (9)
C3—C2—C1	121.18 (9)	O3—C11—C12	115.25 (9)
C3—C2—H2B	119.4	C10—C11—C12	120.44 (9)
C1—C2—H2B	119.4	O4—C12—C13	125.91 (9)
C2—C3—C4	120.09 (9)	O4—C12—C11	114.55 (9)
C2—C3—H3B	120.0	C13—C12—C11	119.53 (9)
C4—C3—H3B	120.0	C12—C13—C14	119.73 (10)
O2—C4—C3	117.26 (9)	C12—C13—H13A	120.1
O2—C4—C5	123.26 (9)	C14—C13—H13A	120.1
C3—C4—C5	119.48 (9)	C9—C14—C13	121.04 (10)
C6—C5—C4	120.11 (9)	C9—C14—H14A	119.5
C6—C5—H5A	119.9	C13—C14—H14A	119.5
C4—C5—H5A	119.9	O4—C15—H15D	109.5
C5—C6—C1	120.83 (9)	O4—C15—H15A	109.5
C5—C6—H6A	119.6	H15D—C15—H15A	109.5
C1—C6—H6A	119.6	O4—C15—H15B	109.5
O1—C7—N1	120.39 (9)	H15D—C15—H15B	109.5
O1—C7—C1	121.31 (9)	H15A—C15—H15B	109.5
N1—C7—C1	118.28 (8)
C7—N1—N2—C8	170.09 (9)	N2—C8—C9—C14	165.34 (12)
C6—C1—C2—C3	2.04 (16)	N2—C8—C9—C10	−14.19 (17)
C7—C1—C2—C3	−176.66 (10)	C14—C9—C10—C11	−0.25 (16)
C1—C2—C3—C4	−0.29 (18)	C8—C9—C10—C11	179.28 (10)
C2—C3—C4—O2	178.66 (10)	C9—C10—C11—O3	−179.40 (9)
C2—C3—C4—C5	−2.01 (17)	C9—C10—C11—C12	−1.60 (15)
O2—C4—C5—C6	−178.17 (10)	C15—O4—C12—C13	−1.45 (17)
C3—C4—C5—C6	2.53 (16)	C15—O4—C12—C11	179.62 (10)
C4—C5—C6—C1	−0.77 (17)	O3—C11—C12—O4	−1.13 (13)
C2—C1—C6—C5	−1.50 (16)	C10—C11—C12—O4	−179.13 (9)
C7—C1—C6—C5	177.08 (10)	O3—C11—C12—C13	179.87 (11)
N2—N1—C7—O1	−3.15 (14)	C10—C11—C12—C13	1.87 (16)
N2—N1—C7—C1	178.39 (8)	O4—C12—C13—C14	−179.17 (12)
C2—C1—C7—O1	3.16 (14)	C11—C12—C13—C14	−0.3 (2)
C6—C1—C7—O1	−175.44 (10)	C10—C9—C14—C13	1.8 (2)
C2—C1—C7—N1	−178.39 (9)	C8—C9—C14—C13	−177.71 (13)
C6—C1—C7—N1	3.01 (15)	C12—C13—C14—C9	−1.6 (2)
N1—N2—C8—C9	178.77 (9)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.88	2.30	2.9798 (12)	134
N1—H1A···O4i	0.88	2.53	3.3542 (12)	156
O2—H2A···O1ii	0.84	1.89	2.7259 (11)	174
O3—H3A···O1iii	0.84	1.88	2.6762 (13)	157
C10—H10A···O2iv	0.95	2.58	3.4786 (14)	158
C15—H15B···Cg1v	0.98	2.85	3.7211 (16)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.88	2.30	2.9798 (12)	134
N1—H1A⋯O4i	0.88	2.53	3.3542 (12)	156
O2—H2A⋯O1ii	0.84	1.89	2.7259 (11)	174
O3—H3A⋯O1iii	0.84	1.88	2.6762 (13)	157
C10—H10A⋯O2iv	0.95	2.58	3.4786 (14)	158
C15—H15B⋯Cg1v	0.98	2.85	3.7211 (16)	149

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