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

In the title compound, C(15)H(14)N(2)O(4), the N=C double bond has an E configuration. The two benzene rings make a dihedral angle of 28.59 (6)°. In the crystal, mol-ecules are linked into a three-dimensional network by inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds and stabilized by weak C-H⋯π inter-actions.

Related literature

For the pharmacological activity of Schiff bases derivatives, see: Zia-ur-Rehman et al. (2009 ▶); Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶). For the biological activity of n class="Chemical">hydrazide derivatives, see: Waisser et al. (1990 ▶); Hall et al. (1993 ▶); Salhin et al. (2007 ▶, 2009 ▶); Tameem et al. (2006 ▶, 2007 ▶, 2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Orthorhombic,

a = 10.9034 (3) Å

b = 8.5533 (2) Å

c = 14.7437 (4) Å

V = 1375.00 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.43 × 0.34 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.958, T max = 0.984

8269 measured reflections

2098 independent reflections

2033 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 1.03

2098 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.33 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 datablocks global, I. DOI: 10.1107/S1600536810045162/fj2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045162/fj2361Isup2.hkl

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

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.383 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5243 reflections
a = 10.9034 (3) Å	θ = 2.8–30.1°
b = 8.5533 (2) Å	µ = 0.10 mm−1
c = 14.7437 (4) Å	T = 100 K
V = 1375.00 (6) Å3	Plate, yellow
Z = 4	0.43 × 0.34 × 0.16 mm

Bruker SMART APEXII CCD area-detector diffractometer	2098 independent reflections
Radiation source: fine-focus sealed tube	2033 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→15
Tmin = 0.958, Tmax = 0.984	k = −12→8
8269 measured reflections	l = −18→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0687P)2 + 0.0626P] where P = (Fo2 + 2Fc2)/3
2098 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.35 e Å−3
1 restraint	Δρmin = −0.32 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	0.50848 (11)	−0.29559 (13)	−0.39327 (7)	0.0176 (2)
O2	0.47208 (11)	0.16057 (13)	−0.05335 (7)	0.0185 (2)
O3	0.72455 (10)	0.71644 (12)	0.21457 (7)	0.0135 (2)
O4	0.84067 (11)	0.96468 (12)	0.16052 (7)	0.0172 (2)
N1	0.59306 (12)	0.30690 (14)	−0.14694 (8)	0.0134 (2)
N2	0.61084 (12)	0.41786 (14)	−0.07972 (8)	0.0130 (2)
C1	0.51462 (13)	0.09777 (17)	−0.29247 (9)	0.0122 (3)
H1A	0.5163	0.2022	−0.3099	0.015*
C2	0.51039 (13)	−0.01823 (17)	−0.35842 (9)	0.0131 (3)
H2A	0.5080	0.0083	−0.4196	0.016*
C3	0.50984 (13)	−0.17538 (18)	−0.33189 (10)	0.0133 (3)
C4	0.51091 (14)	−0.21469 (17)	−0.23966 (9)	0.0149 (3)
H4A	0.5106	−0.3191	−0.2221	0.018*
C5	0.51242 (13)	−0.09687 (17)	−0.17432 (9)	0.0138 (3)
H5A	0.5107	−0.1230	−0.1131	0.017*
C6	0.51643 (13)	0.05963 (16)	−0.20017 (9)	0.0115 (3)
C7	0.52375 (13)	0.17934 (17)	−0.12730 (9)	0.0127 (3)
C8	0.68511 (14)	0.52860 (17)	−0.10081 (9)	0.0133 (3)
H8A	0.7178	0.5333	−0.1590	0.016*
C9	0.71871 (13)	0.64765 (17)	−0.03369 (9)	0.0127 (3)
C10	0.78103 (14)	0.78203 (17)	−0.06151 (10)	0.0148 (3)
H10A	0.7962	0.7984	−0.1228	0.018*
C11	0.82067 (14)	0.89195 (17)	0.00196 (10)	0.0153 (3)
H11A	0.8615	0.9815	−0.0172	0.018*
C12	0.79915 (14)	0.86768 (16)	0.09385 (9)	0.0130 (3)
C13	0.73610 (12)	0.73180 (16)	0.12227 (9)	0.0114 (3)
C14	0.69530 (14)	0.62378 (17)	0.05952 (10)	0.0127 (3)
H14A	0.6526	0.5356	0.0786	0.015*
C15	0.67731 (14)	0.57037 (17)	0.24666 (10)	0.0159 (3)
H15A	0.6747	0.5713	0.3117	0.024*
H15B	0.7295	0.4869	0.2265	0.024*
H15C	0.5961	0.5549	0.2232	0.024*
H1N1	0.638 (2)	0.311 (2)	−0.1935 (17)	0.018 (5)*
H1O1	0.501 (2)	−0.252 (3)	−0.442 (2)	0.043 (8)*
H1O4	0.890 (2)	1.034 (3)	0.138 (2)	0.033 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0328 (6)	0.0102 (5)	0.0099 (4)	0.0016 (4)	−0.0035 (4)	−0.0002 (4)
O2	0.0279 (6)	0.0167 (5)	0.0109 (4)	−0.0050 (4)	0.0046 (4)	−0.0017 (4)
O3	0.0187 (5)	0.0131 (5)	0.0088 (4)	−0.0029 (4)	0.0002 (4)	0.0007 (3)
O4	0.0272 (6)	0.0118 (5)	0.0125 (4)	−0.0068 (4)	−0.0022 (4)	−0.0013 (4)
N1	0.0181 (5)	0.0127 (5)	0.0093 (5)	−0.0021 (4)	0.0027 (4)	−0.0035 (4)
N2	0.0181 (6)	0.0111 (5)	0.0099 (5)	−0.0010 (4)	−0.0003 (4)	−0.0031 (4)
C1	0.0153 (6)	0.0109 (6)	0.0104 (5)	−0.0005 (5)	−0.0001 (5)	0.0011 (5)
C2	0.0182 (7)	0.0101 (6)	0.0109 (6)	−0.0001 (5)	−0.0016 (5)	0.0000 (4)
C3	0.0178 (6)	0.0114 (6)	0.0109 (6)	0.0002 (5)	−0.0012 (5)	−0.0009 (5)
C4	0.0228 (7)	0.0106 (6)	0.0111 (6)	−0.0009 (5)	−0.0013 (5)	0.0014 (5)
C5	0.0190 (7)	0.0127 (7)	0.0096 (5)	−0.0011 (5)	−0.0010 (5)	0.0005 (5)
C6	0.0142 (6)	0.0109 (6)	0.0095 (5)	−0.0012 (5)	0.0001 (5)	−0.0019 (5)
C7	0.0159 (6)	0.0120 (6)	0.0104 (6)	0.0003 (5)	−0.0003 (5)	−0.0014 (5)
C8	0.0165 (7)	0.0137 (6)	0.0099 (5)	0.0002 (5)	0.0003 (5)	−0.0017 (4)
C9	0.0152 (6)	0.0127 (6)	0.0101 (5)	−0.0003 (5)	−0.0007 (4)	−0.0015 (4)
C10	0.0192 (7)	0.0141 (6)	0.0112 (5)	−0.0019 (5)	0.0010 (5)	−0.0003 (5)
C11	0.0212 (7)	0.0122 (6)	0.0125 (6)	−0.0026 (5)	0.0003 (5)	0.0006 (5)
C12	0.0174 (6)	0.0104 (6)	0.0111 (5)	−0.0001 (5)	−0.0008 (5)	−0.0008 (5)
C13	0.0135 (6)	0.0110 (6)	0.0099 (6)	0.0003 (5)	−0.0003 (5)	0.0008 (4)
C14	0.0142 (6)	0.0117 (6)	0.0122 (5)	−0.0015 (5)	0.0000 (5)	0.0004 (5)
C15	0.0211 (7)	0.0145 (6)	0.0119 (6)	−0.0026 (5)	0.0010 (5)	0.0030 (5)

O1—C3	1.3698 (17)	C4—H4A	0.9300
O1—H1O1	0.82 (3)	C5—C6	1.393 (2)
O2—C7	1.2377 (18)	C5—H5A	0.9300
O3—C13	1.3729 (16)	C6—C7	1.4862 (18)
O3—C15	1.4318 (17)	C8—C9	1.4664 (18)
O4—C12	1.3637 (17)	C8—H8A	0.9300
O4—H1O4	0.86 (3)	C9—C10	1.397 (2)
N1—C7	1.3584 (19)	C9—C14	1.4127 (18)
N1—N2	1.3859 (15)	C10—C11	1.395 (2)
N1—H1N1	0.84 (2)	C10—H10A	0.9300
N2—C8	1.2844 (19)	C11—C12	1.3905 (19)
C1—C2	1.3900 (19)	C11—H11A	0.9300
C1—C6	1.3995 (19)	C12—C13	1.4139 (19)
C1—H1A	0.9300	C13—C14	1.3811 (19)
C2—C3	1.400 (2)	C14—H14A	0.9300
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.4008 (19)	C15—H15B	0.9600
C4—C5	1.3943 (19)	C15—H15C	0.9600
C3—O1—H1O1	104 (2)	N2—C8—C9	120.42 (12)
C13—O3—C15	116.36 (11)	N2—C8—H8A	119.8
C12—O4—H1O4	110.3 (18)	C9—C8—H8A	119.8
C7—N1—N2	118.39 (11)	C10—C9—C14	119.50 (12)
C7—N1—H1N1	122.1 (14)	C10—C9—C8	119.66 (12)
N2—N1—H1N1	118.1 (14)	C14—C9—C8	120.73 (12)
C8—N2—N1	114.84 (11)	C11—C10—C9	120.55 (13)
C2—C1—C6	120.95 (13)	C11—C10—H10A	119.7
C2—C1—H1A	119.5	C9—C10—H10A	119.7
C6—C1—H1A	119.5	C12—C11—C10	120.04 (14)
C1—C2—C3	119.35 (13)	C12—C11—H11A	120.0
C1—C2—H2A	120.3	C10—C11—H11A	120.0
C3—C2—H2A	120.3	O4—C12—C11	123.74 (13)
O1—C3—C2	122.42 (13)	O4—C12—C13	116.61 (12)
O1—C3—C4	117.47 (13)	C11—C12—C13	119.57 (13)
C2—C3—C4	120.11 (13)	O3—C13—C14	124.78 (12)
C5—C4—C3	119.82 (14)	O3—C13—C12	114.65 (12)
C5—C4—H4A	120.1	C14—C13—C12	120.53 (12)
C3—C4—H4A	120.1	C13—C14—C9	119.79 (13)
C6—C5—C4	120.40 (13)	C13—C14—H14A	120.1
C6—C5—H5A	119.8	C9—C14—H14A	120.1
C4—C5—H5A	119.8	O3—C15—H15A	109.5
C5—C6—C1	119.33 (13)	O3—C15—H15B	109.5
C5—C6—C7	117.78 (12)	H15A—C15—H15B	109.5
C1—C6—C7	122.89 (13)	O3—C15—H15C	109.5
O2—C7—N1	123.04 (13)	H15A—C15—H15C	109.5
O2—C7—C6	121.53 (13)	H15B—C15—H15C	109.5
N1—C7—C6	115.41 (12)
C7—N1—N2—C8	174.70 (13)	N2—C8—C9—C10	−168.42 (14)
C6—C1—C2—C3	−1.0 (2)	N2—C8—C9—C14	15.4 (2)
C1—C2—C3—O1	−178.53 (13)	C14—C9—C10—C11	0.3 (2)
C1—C2—C3—C4	1.3 (2)	C8—C9—C10—C11	−175.92 (14)
O1—C3—C4—C5	179.95 (13)	C9—C10—C11—C12	0.5 (2)
C2—C3—C4—C5	0.1 (2)	C10—C11—C12—O4	176.23 (14)
C3—C4—C5—C6	−1.9 (2)	C10—C11—C12—C13	−0.5 (2)
C4—C5—C6—C1	2.2 (2)	C15—O3—C13—C14	6.3 (2)
C4—C5—C6—C7	−177.19 (13)	C15—O3—C13—C12	−171.28 (12)
C2—C1—C6—C5	−0.8 (2)	O4—C12—C13—O3	0.37 (18)
C2—C1—C6—C7	178.59 (13)	C11—C12—C13—O3	177.34 (14)
N2—N1—C7—O2	2.8 (2)	O4—C12—C13—C14	−177.32 (13)
N2—N1—C7—C6	−175.54 (12)	C11—C12—C13—C14	−0.3 (2)
C5—C6—C7—O2	−34.2 (2)	O3—C13—C14—C9	−176.25 (13)
C1—C6—C7—O2	146.44 (15)	C12—C13—C14—C9	1.2 (2)
C5—C6—C7—N1	144.17 (13)	C10—C9—C14—C13	−1.2 (2)
C1—C6—C7—N1	−35.2 (2)	C8—C9—C14—C13	175.02 (13)
N1—N2—C8—C9	−175.73 (12)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.84 (2)	2.18 (2)	2.9534 (16)	153.0 (17)
N1—H1N1···O4i	0.84 (2)	2.53 (2)	3.2252 (16)	140.0 (17)
O1—H1O1···O2ii	0.81 (3)	1.84 (3)	2.6361 (15)	165 (2)
O4—H1O4···O1iii	0.87 (2)	1.89 (2)	2.7457 (16)	170 (3)
C2—H2A···O2ii	0.93	2.45	3.1271 (17)	129
C15—H15B···Cg1iv	0.96	2.81	3.5620 (14)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.84 (2)	2.18 (2)	2.9534 (16)	153.0 (17)
N1—H1N1⋯O4i	0.84 (2)	2.53 (2)	3.2252 (16)	140.0 (17)
O1—H1O1⋯O2ii	0.81 (3)	1.84 (3)	2.6361 (15)	165 (2)
O4—H1O4⋯O1iii	0.87 (2)	1.89 (2)	2.7457 (16)	170 (3)
C2—H2A⋯O2ii	0.93	2.45	3.1271 (17)	129
C15—H15B⋯Cg1iv	0.96	2.81	3.5620 (14)	132

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