2-{[2-(2-Hy-droxy-3-meth-oxy-benzyl-idene)hydrazin-1-yl-idene]meth-yl}-6-meth-oxy-phenol.

The title compound, C(16)H(16)N(2)O(4), was obtained from the reaction of hydrazine hydrate and o-vanilin in absolute ethanol. The mol-ecule is almost planar (except for the methyl H atoms), with a mean deviation from the plane of 0.0259 Å. The mol-ecular structure also exhibits an approximate non-crystallographic twofold axis. Intra-molecular O-H⋯N hydrogen bonds occur. In the crystal, inter-molecular C-H⋯O hydrogen bonds generate mol-ecular zigzag sheets. The sheets stack through C-H⋯π inter-actions, leading to a three-dimensional-network.

Related literature

For the properties and applications of the title compound or similar structural compounds and their metal complexes, see: Lin et al. (2009 ▶); Davidson et al. (2006 ▶); Lin & Zeng (2006 ▶).

Experimental

Crystal data

C16H16N2O4

M = 300.31

Monoclinic,

a = 6.3095 (14) Å

b = 17.405 (4) Å

c = 13.606 (3) Å

β = 95.590 (4)°

V = 1487.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.858, T max = 1.000

7393 measured reflections

2648 independent reflections

1133 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.186

S = 1.07

2648 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536811036816/fl2353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036816/fl2353Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036816/fl2353Isup3.cml

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

C16H16N2O4	F(000) = 632
Mr = 300.31	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.3095 (14) Å	Cell parameters from 8451 reflections
b = 17.405 (4) Å	θ = 1.9–26.6°
c = 13.606 (3) Å	µ = 0.10 mm−1
β = 95.590 (4)°	T = 296 K
V = 1487.0 (6) Å3	Block, yellow
Z = 4	0.25 × 0.20 × 0.18 mm

Bruker SMART 1K CCD area-detector diffractometer	2648 independent reflections
Radiation source: fine-focus sealed tube	1133 reflections with I > 2σ(I)
graphite	Rint = 0.052
thin–slice ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→7
Tmin = 0.858, Tmax = 1.000	k = −18→20
7393 measured reflections	l = −15→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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3
2648 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 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
O2	1.1229 (5)	0.30718 (16)	0.11097 (19)	0.0657 (8)
O3	0.3751 (4)	0.44682 (15)	0.36771 (19)	0.0659 (8)
N2	0.6605 (5)	0.39741 (18)	0.2529 (2)	0.0603 (9)
N1	0.8399 (5)	0.35841 (17)	0.2254 (2)	0.0593 (9)
C4	1.1395 (6)	0.28216 (19)	0.2861 (3)	0.0529 (10)
O1	1.4697 (4)	0.23030 (15)	0.09342 (18)	0.0708 (8)
C2	1.4056 (6)	0.2325 (2)	0.1861 (3)	0.0533 (10)
O4	0.0317 (4)	0.52385 (14)	0.38754 (18)	0.0696 (8)
C14	0.0966 (6)	0.5236 (2)	0.2954 (3)	0.0555 (10)
C3	1.2189 (6)	0.27497 (19)	0.1943 (3)	0.0513 (9)
C15	0.2831 (6)	0.4809 (2)	0.2850 (3)	0.0532 (10)
C13	−0.0034 (6)	0.5612 (2)	0.2144 (3)	0.0628 (11)
H13A	−0.1247	0.5904	0.2210	0.075*
C10	0.3625 (6)	0.4756 (2)	0.1936 (3)	0.0570 (10)
C8	0.9494 (6)	0.3256 (2)	0.2985 (3)	0.0585 (11)
H8A	0.9043	0.3300	0.3613	0.070*
C11	0.2542 (7)	0.5129 (2)	0.1132 (3)	0.0702 (12)
H11A	0.3043	0.5086	0.0514	0.084*
C5	1.2488 (6)	0.2463 (2)	0.3685 (3)	0.0638 (11)
H5A	1.1981	0.2512	0.4301	0.077*
C7	1.5070 (6)	0.1973 (2)	0.2683 (3)	0.0624 (11)
H7A	1.6292	0.1684	0.2627	0.075*
C9	0.5516 (6)	0.4314 (2)	0.1809 (3)	0.0633 (11)
H9A	0.5963	0.4273	0.1179	0.076*
C6	1.4279 (7)	0.2047 (2)	0.3592 (3)	0.0674 (11)
H6A	1.4980	0.1810	0.4144	0.081*
C16	−0.1522 (6)	0.5682 (2)	0.4042 (3)	0.0783 (14)
H16A	−0.1799	0.5635	0.4721	0.117*
H16B	−0.2728	0.5497	0.3624	0.117*
H16C	−0.1274	0.6211	0.3893	0.117*
C12	0.0759 (7)	0.5556 (2)	0.1232 (3)	0.0731 (12)
H12A	0.0079	0.5810	0.0688	0.088*
C1	1.6443 (6)	0.1816 (2)	0.0767 (3)	0.0817 (14)
H1B	1.6730	0.1854	0.0089	0.123*
H1C	1.6095	0.1294	0.0914	0.123*
H1D	1.7680	0.1972	0.1186	0.123*
H3A	0.490 (8)	0.421 (3)	0.349 (4)	0.128 (19)*
H2A	1.007 (7)	0.328 (2)	0.131 (3)	0.096 (16)*

	U11	U22	U33	U12	U13	U23
O2	0.0594 (19)	0.080 (2)	0.0581 (18)	0.0130 (15)	0.0097 (15)	0.0022 (14)
O3	0.0600 (19)	0.0752 (19)	0.0638 (19)	0.0177 (15)	0.0130 (15)	0.0115 (14)
N2	0.052 (2)	0.060 (2)	0.071 (2)	0.0020 (16)	0.0164 (17)	−0.0059 (17)
N1	0.049 (2)	0.060 (2)	0.071 (2)	0.0004 (16)	0.0146 (18)	−0.0089 (17)
C4	0.055 (2)	0.051 (2)	0.053 (2)	−0.0052 (18)	0.0082 (19)	−0.0062 (18)
O1	0.0661 (18)	0.0868 (19)	0.0619 (18)	0.0217 (15)	0.0187 (14)	0.0032 (14)
C2	0.050 (2)	0.055 (2)	0.055 (2)	0.0014 (19)	0.0069 (19)	−0.0041 (18)
O4	0.0630 (18)	0.0796 (19)	0.0691 (18)	0.0180 (15)	0.0214 (14)	0.0114 (14)
C14	0.049 (2)	0.055 (2)	0.063 (3)	−0.0023 (19)	0.008 (2)	0.0028 (19)
C3	0.050 (2)	0.052 (2)	0.052 (2)	−0.0001 (19)	0.0042 (18)	−0.0021 (18)
C15	0.052 (2)	0.051 (2)	0.056 (2)	−0.0026 (19)	0.0052 (19)	0.0064 (18)
C13	0.056 (3)	0.059 (3)	0.073 (3)	0.0026 (19)	0.003 (2)	0.007 (2)
C10	0.054 (2)	0.054 (2)	0.064 (3)	−0.0039 (19)	0.009 (2)	−0.0012 (19)
C8	0.056 (3)	0.059 (2)	0.062 (3)	−0.006 (2)	0.015 (2)	−0.011 (2)
C11	0.071 (3)	0.081 (3)	0.059 (3)	−0.003 (2)	0.010 (2)	0.002 (2)
C5	0.071 (3)	0.068 (3)	0.053 (3)	−0.007 (2)	0.008 (2)	−0.007 (2)
C7	0.058 (3)	0.059 (3)	0.070 (3)	0.008 (2)	0.005 (2)	0.000 (2)
C9	0.065 (3)	0.060 (3)	0.067 (3)	−0.005 (2)	0.020 (2)	−0.008 (2)
C6	0.074 (3)	0.068 (3)	0.059 (3)	0.010 (2)	0.001 (2)	0.0008 (19)
C16	0.054 (3)	0.093 (3)	0.091 (3)	0.018 (2)	0.021 (2)	0.006 (2)
C12	0.067 (3)	0.079 (3)	0.071 (3)	0.005 (2)	−0.005 (2)	0.009 (2)
C1	0.065 (3)	0.098 (3)	0.085 (3)	0.019 (3)	0.023 (2)	−0.004 (2)

O2—C3	1.354 (4)	C13—H13A	0.9300
O2—H2A	0.88 (4)	C10—C11	1.392 (5)
O3—C15	1.352 (4)	C10—C9	1.445 (5)
O3—H3A	0.91 (5)	C8—H8A	0.9300
N2—C9	1.285 (4)	C11—C12	1.366 (5)
N2—N1	1.402 (4)	C11—H11A	0.9300
N1—C8	1.288 (4)	C5—C6	1.359 (5)
C4—C3	1.396 (4)	C5—H5A	0.9300
C4—C5	1.404 (5)	C7—C6	1.384 (5)
C4—C8	1.441 (5)	C7—H7A	0.9300
O1—C2	1.361 (4)	C9—H9A	0.9300
O1—C1	1.426 (4)	C6—H6A	0.9300
C2—C7	1.377 (5)	C16—H16A	0.9600
C2—C3	1.404 (5)	C16—H16B	0.9600
O4—C14	1.357 (4)	C16—H16C	0.9600
O4—C16	1.430 (4)	C12—H12A	0.9300
C14—C13	1.380 (5)	C1—H1B	0.9600
C14—C15	1.411 (5)	C1—H1C	0.9600
C15—C10	1.388 (5)	C1—H1D	0.9600
C13—C12	1.385 (5)
C3—O2—H2A	103 (3)	C12—C11—C10	121.4 (4)
C15—O3—H3A	106 (3)	C12—C11—H11A	119.3
C9—N2—N1	113.9 (3)	C10—C11—H11A	119.3
C8—N1—N2	113.3 (3)	C6—C5—C4	120.7 (3)
C3—C4—C5	118.9 (3)	C6—C5—H5A	119.6
C3—C4—C8	121.8 (4)	C4—C5—H5A	119.6
C5—C4—C8	119.3 (3)	C2—C7—C6	120.3 (4)
C2—O1—C1	117.9 (3)	C2—C7—H7A	119.8
O1—C2—C7	125.7 (3)	C6—C7—H7A	119.8
O1—C2—C3	114.6 (3)	N2—C9—C10	122.7 (3)
C7—C2—C3	119.8 (3)	N2—C9—H9A	118.6
C14—O4—C16	118.1 (3)	C10—C9—H9A	118.6
O4—C14—C13	125.5 (3)	C5—C6—C7	120.6 (4)
O4—C14—C15	115.1 (3)	C5—C6—H6A	119.7
C13—C14—C15	119.4 (3)	C7—C6—H6A	119.7
O2—C3—C4	122.8 (3)	O4—C16—H16A	109.5
O2—C3—C2	117.5 (3)	O4—C16—H16B	109.5
C4—C3—C2	119.7 (4)	H16A—C16—H16B	109.5
O3—C15—C10	123.6 (3)	O4—C16—H16C	109.5
O3—C15—C14	116.3 (3)	H16A—C16—H16C	109.5
C10—C15—C14	120.1 (4)	H16B—C16—H16C	109.5
C14—C13—C12	120.3 (4)	C11—C12—C13	120.0 (4)
C14—C13—H13A	119.8	C11—C12—H12A	120.0
C12—C13—H13A	119.8	C13—C12—H12A	120.0
C15—C10—C11	118.7 (4)	O1—C1—H1B	109.5
C15—C10—C9	121.1 (4)	O1—C1—H1C	109.5
C11—C10—C9	120.1 (3)	H1B—C1—H1C	109.5
N1—C8—C4	122.2 (3)	O1—C1—H1D	109.5
N1—C8—H8A	118.9	H1B—C1—H1D	109.5
C4—C8—H8A	118.9	H1C—C1—H1D	109.5

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.91 (5)	1.82 (5)	2.640 (4)	149 (4)
O2—H2A···N1	0.88 (4)	1.82 (4)	2.636 (4)	153 (4)
C16—H16A···O4i	0.96	2.55	3.279 (5)	133
C7—H7A···Cg2ii	0.93	2.90	3.694 (4)	144
C13—H13A···Cg1iii	0.93	2.89	3.717 (4)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2	0.91 (5)	1.82 (5)	2.640 (4)	149 (4)
O2—H2A⋯N1	0.88 (4)	1.82 (4)	2.636 (4)	153 (4)
C16—H16A⋯O4i	0.96	2.55	3.279 (5)	133
C7—H7A⋯Cg2ii	0.93	2.90	3.694 (4)	144
C13—H13A⋯Cg1iii	0.93	2.89	3.717 (4)	149

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