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

In the title compound, C(15)H(14)N(2)O(4), the dihedral angle between the benzene rings is 40.59 (4)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, N-H⋯O, O-H⋯O and C-H⋯O inter-actions link the mol-ecules into a three-dimensional network.

Related literature

For a related sturucture and background to the properties and uses of hydrazones, see: Tameem et al. (2008 ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Monoclinic,

a = 15.1982 (2) Å

b = 8.2416 (1) Å

c = 10.7900 (1) Å

β = 101.173 (1)°

V = 1325.91 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.43 × 0.28 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.956, T max = 0.982

21103 measured reflections

5357 independent reflections

4446 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.122

S = 1.05

5357 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.26 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/S1600536812027201/hb6854sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027201/hb6854Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027201/hb6854Isup3.cml

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

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.434 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9753 reflections
a = 15.1982 (2) Å	θ = 2.7–35.0°
b = 8.2416 (1) Å	µ = 0.11 mm−1
c = 10.7900 (1) Å	T = 100 K
β = 101.173 (1)°	Block, yellow
V = 1325.91 (3) Å3	0.43 × 0.28 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	5357 independent reflections
Radiation source: fine-focus sealed tube	4446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 34.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→22
Tmin = 0.956, Tmax = 0.982	k = −10→12
21103 measured reflections	l = −16→16

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) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.4059P] where P = (Fo2 + 2Fc2)/3
5357 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.26 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	0.31723 (4)	0.31882 (9)	0.55171 (6)	0.01663 (14)
O2	0.51966 (4)	0.76437 (9)	0.99737 (6)	0.01740 (14)
O3	0.09841 (4)	0.09665 (9)	0.36222 (6)	0.01737 (14)
O4	−0.20519 (4)	−0.02273 (9)	0.21628 (6)	0.01959 (14)
N1	0.19965 (5)	0.38654 (10)	0.64137 (7)	0.01474 (14)
N2	0.14157 (5)	0.29962 (10)	0.55201 (7)	0.01408 (14)
C1	0.32956 (6)	0.51526 (12)	0.85518 (8)	0.01642 (16)
H1A	0.2780	0.4682	0.8784	0.020*
C2	0.38846 (6)	0.60648 (12)	0.94252 (8)	0.01661 (17)
H2A	0.3774	0.6206	1.0255	0.020*
C3	0.46390 (6)	0.67757 (11)	0.90881 (8)	0.01411 (15)
C4	0.47939 (6)	0.65803 (11)	0.78597 (8)	0.01494 (16)
H4A	0.5297	0.7085	0.7618	0.018*
C5	0.42107 (6)	0.56481 (11)	0.69974 (8)	0.01445 (15)
H5A	0.4324	0.5500	0.6170	0.017*
C6	0.34575 (5)	0.49233 (11)	0.73292 (8)	0.01322 (15)
C7	0.28800 (5)	0.39174 (11)	0.63549 (8)	0.01329 (15)
C8	0.05729 (6)	0.31976 (11)	0.55158 (8)	0.01372 (15)
H8A	0.0393	0.3916	0.6109	0.016*
C9	−0.01035 (5)	0.23455 (10)	0.46203 (8)	0.01278 (15)
C10	0.01179 (6)	0.12335 (11)	0.37274 (8)	0.01310 (15)
C11	−0.05540 (6)	0.03854 (11)	0.29367 (8)	0.01457 (15)
H11A	−0.0402	−0.0385	0.2357	0.017*
C12	−0.14544 (6)	0.06598 (11)	0.29894 (8)	0.01454 (15)
C13	−0.16902 (6)	0.17757 (11)	0.38464 (8)	0.01555 (16)
H13A	−0.2302	0.1976	0.3872	0.019*
C14	−0.10109 (6)	0.25820 (11)	0.46569 (8)	0.01491 (16)
H14A	−0.1166	0.3319	0.5257	0.018*
C15	−0.29779 (6)	−0.01043 (14)	0.22528 (9)	0.02144 (19)
H15A	−0.3334	−0.0854	0.1651	0.032*
H15B	−0.3187	0.1008	0.2058	0.032*
H15C	−0.3046	−0.0383	0.3112	0.032*
H1N1	0.1785 (10)	0.4363 (19)	0.6991 (14)	0.029 (4)*
H1O3	0.1324 (12)	0.155 (2)	0.4189 (18)	0.047 (5)*
H1O2	0.5723 (12)	0.788 (2)	0.9722 (16)	0.039 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0124 (3)	0.0221 (3)	0.0158 (3)	0.0004 (2)	0.0038 (2)	−0.0021 (2)
O2	0.0132 (3)	0.0228 (3)	0.0166 (3)	−0.0040 (2)	0.0039 (2)	−0.0049 (2)
O3	0.0116 (3)	0.0226 (3)	0.0186 (3)	0.0009 (2)	0.0045 (2)	−0.0035 (2)
O4	0.0142 (3)	0.0253 (4)	0.0187 (3)	−0.0046 (2)	0.0017 (2)	−0.0060 (3)
N1	0.0103 (3)	0.0188 (4)	0.0152 (3)	−0.0015 (2)	0.0027 (2)	−0.0035 (3)
N2	0.0116 (3)	0.0161 (3)	0.0141 (3)	−0.0019 (2)	0.0016 (2)	−0.0008 (2)
C1	0.0126 (3)	0.0224 (4)	0.0149 (3)	−0.0037 (3)	0.0043 (3)	0.0006 (3)
C2	0.0143 (4)	0.0223 (4)	0.0139 (3)	−0.0030 (3)	0.0044 (3)	−0.0002 (3)
C3	0.0113 (3)	0.0161 (4)	0.0149 (3)	−0.0001 (3)	0.0025 (3)	−0.0004 (3)
C4	0.0121 (3)	0.0178 (4)	0.0157 (3)	−0.0022 (3)	0.0046 (3)	−0.0008 (3)
C5	0.0125 (3)	0.0176 (4)	0.0140 (3)	−0.0012 (3)	0.0043 (3)	−0.0002 (3)
C6	0.0105 (3)	0.0155 (4)	0.0135 (3)	−0.0010 (3)	0.0018 (2)	0.0008 (3)
C7	0.0115 (3)	0.0150 (4)	0.0132 (3)	−0.0004 (3)	0.0022 (2)	0.0022 (3)
C8	0.0119 (3)	0.0153 (4)	0.0139 (3)	−0.0003 (3)	0.0025 (2)	−0.0010 (3)
C9	0.0112 (3)	0.0136 (4)	0.0134 (3)	−0.0002 (3)	0.0022 (2)	0.0001 (3)
C10	0.0117 (3)	0.0151 (4)	0.0130 (3)	0.0009 (3)	0.0036 (2)	0.0011 (3)
C11	0.0151 (4)	0.0152 (4)	0.0138 (3)	−0.0010 (3)	0.0035 (3)	−0.0010 (3)
C12	0.0136 (3)	0.0160 (4)	0.0135 (3)	−0.0025 (3)	0.0015 (3)	0.0005 (3)
C13	0.0112 (3)	0.0179 (4)	0.0176 (4)	−0.0004 (3)	0.0028 (3)	−0.0017 (3)
C14	0.0122 (3)	0.0158 (4)	0.0168 (4)	0.0002 (3)	0.0030 (3)	−0.0026 (3)
C15	0.0145 (4)	0.0278 (5)	0.0210 (4)	−0.0049 (3)	0.0008 (3)	−0.0033 (4)

O1—C7	1.2375 (11)	C4—H4A	0.9500
O2—C3	1.3525 (10)	C5—C6	1.3979 (12)
O2—H1O2	0.915 (18)	C5—H5A	0.9500
O3—C10	1.3610 (10)	C6—C7	1.4849 (12)
O3—H1O3	0.866 (19)	C8—C9	1.4487 (11)
O4—C12	1.3568 (10)	C8—H8A	0.9500
O4—C15	1.4329 (12)	C9—C14	1.4009 (12)
N1—C7	1.3571 (11)	C9—C10	1.4166 (12)
N1—N2	1.3756 (10)	C10—C11	1.3862 (12)
N1—H1N1	0.858 (16)	C11—C12	1.3990 (12)
N2—C8	1.2907 (11)	C11—H11A	0.9500
C1—C2	1.3885 (12)	C12—C13	1.3992 (13)
C1—C6	1.4008 (12)	C13—C14	1.3865 (12)
C1—H1A	0.9500	C13—H13A	0.9500
C2—C3	1.3971 (12)	C14—H14A	0.9500
C2—H2A	0.9500	C15—H15A	0.9800
C3—C4	1.3997 (12)	C15—H15B	0.9800
C4—C5	1.3864 (12)	C15—H15C	0.9800
C3—O2—H1O2	111.6 (11)	N2—C8—C9	121.03 (8)
C10—O3—H1O3	107.8 (12)	N2—C8—H8A	119.5
C12—O4—C15	117.28 (7)	C9—C8—H8A	119.5
C7—N1—N2	119.35 (7)	C14—C9—C10	118.30 (8)
C7—N1—H1N1	122.1 (10)	C14—C9—C8	119.27 (8)
N2—N1—H1N1	118.5 (10)	C10—C9—C8	122.40 (8)
C8—N2—N1	115.92 (7)	O3—C10—C11	118.44 (8)
C2—C1—C6	120.29 (8)	O3—C10—C9	121.49 (8)
C2—C1—H1A	119.9	C11—C10—C9	120.07 (8)
C6—C1—H1A	119.9	C10—C11—C12	120.21 (8)
C1—C2—C3	120.27 (8)	C10—C11—H11A	119.9
C1—C2—H2A	119.9	C12—C11—H11A	119.9
C3—C2—H2A	119.9	O4—C12—C11	114.94 (8)
O2—C3—C2	118.12 (8)	O4—C12—C13	124.33 (8)
O2—C3—C4	122.18 (8)	C11—C12—C13	120.73 (8)
C2—C3—C4	119.70 (8)	C14—C13—C12	118.49 (8)
C5—C4—C3	119.76 (8)	C14—C13—H13A	120.8
C5—C4—H4A	120.1	C12—C13—H13A	120.8
C3—C4—H4A	120.1	C13—C14—C9	122.16 (8)
C4—C5—C6	120.91 (8)	C13—C14—H14A	118.9
C4—C5—H5A	119.5	C9—C14—H14A	118.9
C6—C5—H5A	119.5	O4—C15—H15A	109.5
C5—C6—C1	119.05 (8)	O4—C15—H15B	109.5
C5—C6—C7	117.28 (7)	H15A—C15—H15B	109.5
C1—C6—C7	123.67 (8)	O4—C15—H15C	109.5
O1—C7—N1	121.15 (8)	H15A—C15—H15C	109.5
O1—C7—C6	122.80 (8)	H15B—C15—H15C	109.5
N1—C7—C6	116.04 (7)
C7—N1—N2—C8	−169.85 (8)	N2—C8—C9—C14	179.21 (8)
C6—C1—C2—C3	0.66 (14)	N2—C8—C9—C10	1.28 (13)
C1—C2—C3—O2	−179.55 (8)	C14—C9—C10—O3	178.72 (8)
C1—C2—C3—C4	0.73 (14)	C8—C9—C10—O3	−3.34 (13)
O2—C3—C4—C5	178.60 (8)	C14—C9—C10—C11	−1.39 (13)
C2—C3—C4—C5	−1.68 (14)	C8—C9—C10—C11	176.55 (8)
C3—C4—C5—C6	1.27 (13)	O3—C10—C11—C12	−178.13 (8)
C4—C5—C6—C1	0.11 (13)	C9—C10—C11—C12	1.98 (13)
C4—C5—C6—C7	−178.74 (8)	C15—O4—C12—C11	174.52 (8)
C2—C1—C6—C5	−1.08 (14)	C15—O4—C12—C13	−5.41 (13)
C2—C1—C6—C7	177.70 (9)	C10—C11—C12—O4	179.35 (8)
N2—N1—C7—O1	−0.48 (13)	C10—C11—C12—C13	−0.72 (13)
N2—N1—C7—C6	178.13 (7)	O4—C12—C13—C14	178.82 (8)
C5—C6—C7—O1	28.68 (13)	C11—C12—C13—C14	−1.10 (13)
C1—C6—C7—O1	−150.12 (9)	C12—C13—C14—C9	1.70 (14)
C5—C6—C7—N1	−149.91 (8)	C10—C9—C14—C13	−0.47 (13)
C1—C6—C7—N1	31.29 (12)	C8—C9—C14—C13	−178.48 (8)
N1—N2—C8—C9	−179.89 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.859 (15)	2.342 (15)	3.0800 (10)	144.3 (14)
O3—H1O3···N2	0.866 (18)	1.851 (18)	2.6271 (10)	148.3 (17)
O2—H1O2···O1ii	0.914 (18)	1.766 (18)	2.6713 (9)	170.3 (16)
C5—H5A···O2iii	0.95	2.54	3.2036 (11)	128
C15—H15A···O1iv	0.98	2.53	3.2646 (12)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.859 (15)	2.342 (15)	3.0800 (10)	144.3 (14)
O3—H1O3⋯N2	0.866 (18)	1.851 (18)	2.6271 (10)	148.3 (17)
O2—H1O2⋯O1ii	0.914 (18)	1.766 (18)	2.6713 (9)	170.3 (16)
C5—H5A⋯O2iii	0.95	2.54	3.2036 (11)	128
C15—H15A⋯O1iv	0.98	2.53	3.2646 (12)	132

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