N'-(3,4-Dihy-droxy-benzyl-idene)-2-meth-oxy-benzohydrazide.

The title compound, C(15)H(14)N(2)O(4), was prepared from 3,4-dihy-droxy-benzaldehyde and 2-meth-oxy-benzhydrazide in absolute methanol. An intra-molecular N-H⋯O hydrogen bond makes an S(6) ring motif and the dihedral angle between the aromatic rings is 3.2 (3)°. The meta-O atom is disordered over two positions in a 0.809 (6):0.191 (6) ratio. The crystal structure features O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For the structures and biological aspects of benzohydrazone derivatives, see: Horkaew et al. (2012 ▶); Rassem et al. (2012 ▶); Zhang et al. (2012 ▶); Fun et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶);.

Experimental

Crystal data

C15H14N2O4

M = 286.28

Orthorhombic,

a = 13.796 (2) Å

b = 8.412 (2) Å

c = 24.004 (3) Å

V = 2785.7 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.13 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.987, T max = 0.990

12495 measured reflections

2570 independent reflections

1231 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.159

S = 1.03

2570 reflections

205 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812025688/hb6829sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025688/hb6829Isup2.hkl

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

C15H14N2O4	Dx = 1.365 Mg m−3
Mr = 286.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1590 reflections
a = 13.796 (2) Å	θ = 2.9–26.4°
b = 8.412 (2) Å	µ = 0.10 mm−1
c = 24.004 (3) Å	T = 298 K
V = 2785.7 (9) Å3	Block, colorless
Z = 8	0.13 × 0.10 × 0.10 mm
F(000) = 1200

Bruker SMART 1K CCD area-detector diffractometer	2570 independent reflections
Radiation source: fine-focus sealed tube	1231 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
ω scan	θmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→16
Tmin = 0.987, Tmax = 0.990	k = −10→10
12495 measured reflections	l = −29→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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0613P)2] where P = (Fo2 + 2Fc2)/3
2570 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.24 e Å−3
3 restraints	Δρmin = −0.18 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	Occ. (<1)
N1	0.2622 (2)	0.4522 (3)	0.14012 (12)	0.0466 (8)
N2	0.19869 (19)	0.3787 (3)	0.17652 (11)	0.0447 (7)
O1	0.43832 (18)	0.5280 (3)	0.10901 (11)	0.0693 (8)
O2	0.14022 (18)	0.5770 (3)	0.09575 (10)	0.0661 (8)
O4	0.02926 (17)	−0.0612 (3)	0.37116 (11)	0.0641 (8)
H4	−0.0227	−0.0192	0.3788	0.096*
C1	0.4002 (3)	0.6162 (5)	0.06652 (15)	0.0550 (10)
C2	0.2990 (3)	0.6235 (4)	0.06167 (14)	0.0475 (9)
C3	0.2609 (3)	0.7113 (5)	0.01798 (16)	0.0683 (12)
H3A	0.1939	0.7164	0.0137	0.082*
C4	0.3189 (4)	0.7910 (6)	−0.01924 (18)	0.0890 (15)
H4A	0.2915	0.8488	−0.0482	0.107*
C5	0.4165 (4)	0.7845 (6)	−0.0133 (2)	0.0914 (16)
H5	0.4558	0.8392	−0.0383	0.110*
C6	0.4583 (3)	0.6986 (5)	0.02896 (18)	0.0740 (13)
H6	0.5255	0.6955	0.0325	0.089*
C7	0.5400 (3)	0.5248 (5)	0.11890 (18)	0.0830 (14)
H7A	0.5725	0.4839	0.0866	0.124*
H7B	0.5535	0.4577	0.1503	0.124*
H7C	0.5625	0.6306	0.1265	0.124*
C8	0.2274 (3)	0.5489 (4)	0.10027 (14)	0.0454 (9)
C9	0.2381 (3)	0.2932 (4)	0.21392 (14)	0.0467 (9)
H9	0.3054	0.2881	0.2154	0.056*
C10	0.1824 (2)	0.2036 (4)	0.25412 (14)	0.0417 (8)
C11	0.0823 (2)	0.1919 (4)	0.25076 (14)	0.0468 (9)
H11	0.0500	0.2444	0.2221	0.056*
C13	0.0768 (3)	0.0289 (4)	0.33218 (14)	0.0446 (9)
C15	0.2287 (2)	0.1215 (4)	0.29653 (14)	0.0513 (10)
H15	0.2959	0.1245	0.2991	0.062*
H1	0.3270 (8)	0.446 (4)	0.1439 (15)	0.080*
O3	−0.06579 (19)	0.0949 (4)	0.27963 (12)	0.0658 (13)	0.809 (6)
H3B	−0.0941	0.0894	0.3096	0.099*	0.809 (6)
C12	0.0295 (2)	0.1053 (4)	0.28842 (15)	0.0473 (9)	0.809 (6)
C14	0.1761 (3)	0.0351 (4)	0.33496 (15)	0.0515 (10)	0.809 (6)
H14A	0.2083	−0.0195	0.3631	0.062*	0.809 (6)
O3'	0.2166 (10)	−0.0452 (18)	0.3729 (5)	0.085 (6)	0.191 (6)
H3'A	0.1752	−0.0887	0.3921	0.128*	0.191 (6)
C12'	0.1761 (3)	0.0351 (4)	0.33496 (15)	0.0515 (10)	0.191 (6)
C14'	0.0295 (2)	0.1053 (4)	0.28842 (15)	0.0473 (9)	0.191 (6)
H14B	−0.0375	0.0976	0.2848	0.057*	0.191 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0481 (17)	0.0459 (19)	0.0458 (18)	0.0011 (16)	0.0106 (16)	0.0062 (16)
N2	0.0495 (17)	0.0410 (18)	0.0435 (17)	0.0027 (14)	0.0091 (15)	0.0033 (15)
O1	0.0498 (17)	0.086 (2)	0.0719 (19)	−0.0096 (14)	0.0032 (14)	0.0102 (16)
O2	0.0530 (17)	0.0765 (19)	0.0689 (18)	0.0119 (14)	0.0049 (13)	0.0195 (15)
O4	0.0639 (18)	0.0618 (18)	0.0665 (18)	0.0026 (13)	0.0144 (14)	0.0224 (15)
C1	0.070 (3)	0.051 (2)	0.044 (2)	−0.012 (2)	0.011 (2)	−0.009 (2)
C2	0.063 (2)	0.042 (2)	0.038 (2)	−0.0035 (19)	0.0095 (19)	−0.0021 (18)
C3	0.089 (3)	0.066 (3)	0.051 (3)	0.004 (2)	0.004 (2)	0.009 (2)
C4	0.128 (4)	0.079 (3)	0.060 (3)	−0.003 (3)	0.014 (3)	0.023 (3)
C5	0.135 (5)	0.081 (4)	0.058 (3)	−0.030 (4)	0.033 (3)	0.005 (3)
C6	0.082 (3)	0.078 (3)	0.062 (3)	−0.025 (2)	0.025 (2)	−0.012 (3)
C7	0.059 (3)	0.089 (4)	0.101 (4)	−0.008 (2)	−0.002 (2)	−0.012 (3)
C8	0.060 (3)	0.039 (2)	0.037 (2)	0.0035 (18)	0.0050 (19)	−0.0050 (18)
C9	0.045 (2)	0.046 (2)	0.048 (2)	0.0032 (18)	0.0069 (18)	−0.0037 (19)
C10	0.042 (2)	0.039 (2)	0.044 (2)	0.0030 (17)	0.0043 (18)	−0.0017 (18)
C11	0.054 (2)	0.038 (2)	0.048 (2)	0.0012 (18)	−0.0066 (18)	0.0098 (18)
C13	0.053 (2)	0.035 (2)	0.046 (2)	0.0016 (17)	0.0073 (19)	0.0017 (18)
C15	0.044 (2)	0.062 (3)	0.049 (2)	0.0040 (19)	−0.0021 (18)	0.006 (2)
O3	0.035 (2)	0.078 (3)	0.084 (2)	−0.0011 (16)	0.0014 (15)	0.0331 (18)
C12	0.044 (2)	0.041 (2)	0.058 (2)	0.0004 (17)	−0.0027 (18)	0.0087 (19)
C14	0.055 (2)	0.060 (3)	0.039 (2)	0.011 (2)	−0.005 (2)	0.010 (2)
O3'	0.077 (11)	0.120 (15)	0.059 (11)	−0.005 (9)	0.004 (8)	0.014 (9)
C12'	0.055 (2)	0.060 (3)	0.039 (2)	0.011 (2)	−0.005 (2)	0.010 (2)
C14'	0.044 (2)	0.041 (2)	0.058 (2)	0.0004 (17)	−0.0027 (18)	0.0087 (19)

N1—C8	1.345 (4)	C6—H6	0.9300
N1—N2	1.383 (4)	C7—H7A	0.9600
N1—H1	0.899 (10)	C7—H7B	0.9600
N2—C9	1.273 (4)	C7—H7C	0.9600
O1—C1	1.367 (4)	C9—C10	1.446 (4)
O1—C7	1.423 (4)	C9—H9	0.9300
O2—C8	1.230 (4)	C10—C15	1.386 (4)
O4—C13	1.372 (4)	C10—C11	1.387 (4)
O4—H4	0.8200	C11—C12	1.371 (4)
C1—C6	1.391 (5)	C11—H11	0.9300
C1—C2	1.403 (5)	C13—C14	1.371 (4)
C2—C3	1.386 (5)	C13—C12	1.394 (5)
C2—C8	1.493 (5)	C15—C14	1.381 (4)
C3—C4	1.374 (5)	C15—H15	0.9300
C3—H3A	0.9300	O3—C12	1.334 (4)
C4—C5	1.356 (6)	O3—H3B	0.8200
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.372 (6)	O3'—H3'A	0.8200
C5—H5	0.9300
C8—N1—N2	119.5 (3)	H7A—C7—H7C	109.5
C8—N1—H1	117 (2)	H7B—C7—H7C	109.5
N2—N1—H1	123 (2)	O2—C8—N1	121.9 (3)
C9—N2—N1	115.3 (3)	O2—C8—C2	120.8 (3)
C1—O1—C7	120.9 (3)	N1—C8—C2	117.3 (3)
C13—O4—H4	109.5	N2—C9—C10	122.6 (3)
O1—C1—C6	122.2 (4)	N2—C9—H9	118.7
O1—C1—C2	117.9 (3)	C10—C9—H9	118.7
C6—C1—C2	119.9 (4)	C15—C10—C11	117.8 (3)
C3—C2—C1	117.7 (4)	C15—C10—C9	120.3 (3)
C3—C2—C8	116.2 (3)	C11—C10—C9	121.8 (3)
C1—C2—C8	126.1 (3)	C12—C11—C10	121.9 (3)
C4—C3—C2	122.0 (4)	C12—C11—H11	119.0
C4—C3—H3A	119.0	C10—C11—H11	119.0
C2—C3—H3A	119.0	C14—C13—O4	117.8 (3)
C5—C4—C3	119.4 (5)	C14—C13—C12	119.1 (3)
C5—C4—H4A	120.3	O4—C13—C12	123.0 (3)
C3—C4—H4A	120.3	C14—C15—C10	120.7 (3)
C4—C5—C6	121.1 (5)	C14—C15—H15	119.7
C4—C5—H5	119.4	C10—C15—H15	119.7
C6—C5—H5	119.4	C12—O3—H3B	109.5
C5—C6—C1	119.9 (4)	O3—C12—C11	117.0 (3)
C5—C6—H6	120.0	O3—C12—C13	123.4 (3)
C1—C6—H6	120.0	C11—C12—C13	119.5 (3)
O1—C7—H7A	109.5	C13—C14—C15	120.9 (3)
O1—C7—H7B	109.5	C13—C14—H14A	119.6
H7A—C7—H7B	109.5	C15—C14—H14A	119.6
O1—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2i	0.82	1.91	2.730 (3)	174
O3—H3B···N2i	0.82	2.31	2.789 (4)	118
O3—H3B···O2i	0.82	2.36	3.166 (4)	167
N1—H1···O1	0.90 (1)	1.88 (3)	2.620 (4)	138 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2i	0.82	1.91	2.730 (3)	174
O3—H3B⋯N2i	0.82	2.31	2.789 (4)	118
O3—H3B⋯O2i	0.82	2.36	3.166 (4)	167
N1—H1⋯O1	0.90 (1)	1.88 (3)	2.620 (4)	138 (3)

Symmetry code: (i) .