N'-[(E)-2-Hy-droxy-5-meth-oxy-benzyl-idene]-2-meth-oxy-benzohydrazide.

The mol-ecule of the title compound, C16H16N2O4, adopts an E conformation about the azomethine C=N double bond. The dihedral angle formed by the benzene rings is 18.88 (9)°. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, which forms an S(6) ring. In the crystal, the mol-ecules are linked into chains parallel to [001] by N-H⋯O hydrogen bonds. The chains are further connected into a three-dimensional network by π-π stacking inter-actions with centroid-centroid distances of 3.6538 (10) and 3.8995 (11) Å.

Related literature

For the applications and biological activity of Schiff bases, see: Panneerselvam et al. (2009 ▶); Khan et al. (2009 ▶); Jarahpour et al. (2007 ▶); Pandeya et al. (1999 ▶). For related structures, see: Taha et al. (2012a ▶,b ▶); Lu et al. (2008 ▶).

Experimental

Crystal data

C16H16N2O4

M = 300.31

Monoclinic,

a = 14.5775 (13) Å

b = 11.0798 (11) Å

c = 9.5893 (9) Å

β = 99.872 (2)°

V = 1525.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.59 × 0.45 × 0.39 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.946, T max = 0.964

8886 measured reflections

2767 independent reflections

2210 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.04

2767 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042389/rz5014sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042389/rz5014Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042389/rz5014Isup3.cml

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

C16H16N2O4	F(000) = 632
Mr = 300.31	Dx = 1.307 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3190 reflections
a = 14.5775 (13) Å	θ = 2.3–25.0°
b = 11.0798 (11) Å	µ = 0.10 mm−1
c = 9.5893 (9) Å	T = 273 K
β = 99.872 (2)°	Block, colourless
V = 1525.9 (2) Å3	0.59 × 0.45 × 0.39 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2767 independent reflections
Radiation source: fine-focus sealed tube	2210 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scan	θmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→16
Tmin = 0.946, Tmax = 0.964	k = −13→13
8886 measured reflections	l = −9→11

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) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.1784P] where P = (Fo2 + 2Fc2)/3
2767 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.15 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
O1	0.41411 (11)	0.06306 (13)	0.11043 (13)	0.0918 (4)
O2	0.68838 (9)	0.10138 (14)	0.58074 (17)	0.1009 (4)
O3	0.17476 (9)	0.24072 (14)	0.01591 (12)	0.0957 (5)
O4	0.16599 (8)	0.47356 (10)	0.32496 (12)	0.0767 (3)
N1	0.31001 (9)	0.20202 (11)	0.23724 (13)	0.0618 (3)
N2	0.22889 (9)	0.26092 (12)	0.24670 (14)	0.0634 (4)
C1	0.47885 (12)	0.07530 (15)	0.22962 (18)	0.0714 (5)
C2	0.56411 (15)	0.01986 (17)	0.2354 (2)	0.0881 (6)
H2B	0.5758	−0.0250	0.1584	0.106*
C3	0.63154 (14)	0.03008 (17)	0.3527 (2)	0.0884 (6)
H3A	0.6885	−0.0083	0.3548	0.106*
C4	0.61614 (11)	0.09696 (16)	0.4685 (2)	0.0752 (5)
C5	0.53108 (11)	0.15170 (14)	0.46503 (19)	0.0692 (4)
H5A	0.5198	0.1959	0.5428	0.083*
C6	0.46152 (10)	0.14167 (13)	0.34613 (16)	0.0612 (4)
C7	0.37267 (11)	0.19998 (13)	0.34759 (17)	0.0629 (4)
H7A	0.3612	0.2364	0.4303	0.076*
C8	0.16545 (10)	0.28010 (13)	0.13077 (15)	0.0585 (4)
C9	0.08121 (10)	0.34987 (13)	0.15057 (14)	0.0578 (4)
C10	0.08163 (11)	0.44261 (14)	0.24890 (16)	0.0631 (4)
C11	−0.00098 (14)	0.50192 (17)	0.2600 (2)	0.0822 (5)
H11A	−0.0012	0.5626	0.3270	0.099*
C12	−0.08169 (14)	0.47113 (19)	0.1728 (3)	0.0922 (6)
H12A	−0.1367	0.5106	0.1818	0.111*
C13	−0.08304 (12)	0.3835 (2)	0.0728 (2)	0.0883 (6)
H13A	−0.1383	0.3641	0.0131	0.106*
C14	−0.00128 (12)	0.32362 (16)	0.06098 (18)	0.0743 (5)
H14A	−0.0019	0.2648	−0.0083	0.089*
C15	0.17013 (18)	0.5590 (2)	0.4353 (3)	0.1167 (8)
H15A	0.2339	0.5716	0.4783	0.175*
H15B	0.1357	0.5295	0.5050	0.175*
H15C	0.1437	0.6339	0.3974	0.175*
C16	0.67844 (15)	0.1759 (2)	0.6962 (3)	0.1081 (7)
H16A	0.7359	0.1775	0.7622	0.162*
H16B	0.6299	0.1448	0.7421	0.162*
H16C	0.6628	0.2563	0.6629	0.162*
H2A	0.2202 (11)	0.2826 (14)	0.3268 (18)	0.066 (5)*
H1A	0.3662 (16)	0.101 (2)	0.120 (2)	0.106 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.1031 (10)	0.1066 (10)	0.0695 (8)	0.0320 (8)	0.0257 (7)	−0.0085 (7)
O2	0.0627 (8)	0.1096 (10)	0.1274 (11)	0.0180 (7)	0.0077 (8)	−0.0032 (9)
O3	0.1036 (10)	0.1328 (11)	0.0532 (7)	0.0220 (8)	0.0202 (6)	−0.0145 (7)
O4	0.0744 (8)	0.0750 (7)	0.0801 (7)	0.0077 (6)	0.0118 (6)	−0.0138 (6)
N1	0.0644 (8)	0.0624 (7)	0.0623 (8)	0.0105 (6)	0.0214 (7)	0.0013 (6)
N2	0.0642 (8)	0.0780 (8)	0.0509 (7)	0.0163 (6)	0.0180 (6)	−0.0018 (6)
C1	0.0783 (11)	0.0701 (10)	0.0719 (10)	0.0150 (8)	0.0298 (9)	0.0068 (8)
C2	0.0933 (14)	0.0870 (12)	0.0924 (13)	0.0288 (11)	0.0400 (12)	−0.0002 (10)
C3	0.0740 (12)	0.0836 (12)	0.1166 (16)	0.0274 (10)	0.0418 (12)	0.0122 (11)
C4	0.0571 (10)	0.0719 (10)	0.0989 (12)	0.0093 (8)	0.0204 (9)	0.0092 (9)
C5	0.0634 (10)	0.0658 (9)	0.0826 (11)	0.0059 (7)	0.0241 (9)	−0.0007 (8)
C6	0.0608 (9)	0.0569 (8)	0.0708 (9)	0.0071 (7)	0.0247 (8)	0.0039 (7)
C7	0.0648 (10)	0.0622 (8)	0.0654 (9)	0.0073 (7)	0.0211 (8)	−0.0030 (7)
C8	0.0666 (9)	0.0629 (8)	0.0488 (8)	−0.0017 (7)	0.0180 (7)	0.0036 (6)
C9	0.0581 (9)	0.0632 (8)	0.0539 (8)	0.0000 (7)	0.0142 (7)	0.0152 (6)
C10	0.0643 (10)	0.0622 (8)	0.0654 (9)	0.0052 (7)	0.0183 (8)	0.0104 (7)
C11	0.0774 (12)	0.0749 (11)	0.0991 (13)	0.0142 (9)	0.0293 (10)	0.0068 (9)
C12	0.0663 (12)	0.0863 (13)	0.1271 (17)	0.0149 (10)	0.0258 (12)	0.0237 (12)
C13	0.0587 (11)	0.0930 (13)	0.1090 (15)	−0.0021 (9)	0.0026 (10)	0.0306 (12)
C14	0.0737 (11)	0.0744 (10)	0.0733 (10)	−0.0056 (8)	0.0082 (9)	0.0145 (8)
C15	0.1156 (18)	0.1105 (17)	0.1212 (18)	0.0065 (13)	0.0127 (14)	−0.0508 (14)
C16	0.0801 (14)	0.1211 (18)	0.1162 (17)	0.0058 (12)	−0.0030 (12)	−0.0012 (15)

O1—C1	1.359 (2)	C6—C7	1.450 (2)
O1—H1A	0.84 (2)	C7—H7A	0.9300
O2—C4	1.372 (2)	C8—C9	1.491 (2)
O2—C16	1.408 (3)	C9—C14	1.384 (2)
O3—C8	1.2138 (17)	C9—C10	1.394 (2)
O4—C10	1.362 (2)	C10—C11	1.392 (2)
O4—C15	1.413 (2)	C11—C12	1.365 (3)
N1—C7	1.2740 (18)	C11—H11A	0.9300
N1—N2	1.3671 (17)	C12—C13	1.362 (3)
N2—C8	1.3356 (19)	C12—H12A	0.9300
N2—H2A	0.835 (17)	C13—C14	1.386 (3)
C1—C2	1.379 (2)	C13—H13A	0.9300
C1—C6	1.396 (2)	C14—H14A	0.9300
C2—C3	1.366 (3)	C15—H15A	0.9600
C2—H2B	0.9300	C15—H15B	0.9600
C3—C4	1.385 (3)	C15—H15C	0.9600
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.376 (2)	C16—H16B	0.9600
C5—C6	1.394 (2)	C16—H16C	0.9600
C5—H5A	0.9300
C1—O1—H1A	109.1 (15)	C14—C9—C10	118.52 (15)
C4—O2—C16	117.98 (14)	C14—C9—C8	117.34 (14)
C10—O4—C15	119.23 (15)	C10—C9—C8	124.08 (14)
C7—N1—N2	117.29 (12)	O4—C10—C11	123.63 (16)
C8—N2—N1	120.27 (12)	O4—C10—C9	116.54 (13)
C8—N2—H2A	121.8 (11)	C11—C10—C9	119.75 (16)
N1—N2—H2A	117.9 (11)	C12—C11—C10	120.09 (19)
O1—C1—C2	118.72 (16)	C12—C11—H11A	120.0
O1—C1—C6	122.06 (14)	C10—C11—H11A	120.0
C2—C1—C6	119.22 (17)	C13—C12—C11	121.09 (18)
C3—C2—C1	120.82 (17)	C13—C12—H12A	119.5
C3—C2—H2B	119.6	C11—C12—H12A	119.5
C1—C2—H2B	119.6	C12—C13—C14	119.35 (18)
C2—C3—C4	120.80 (16)	C12—C13—H13A	120.3
C2—C3—H3A	119.6	C14—C13—H13A	120.3
C4—C3—H3A	119.6	C9—C14—C13	121.11 (18)
O2—C4—C5	124.81 (17)	C9—C14—H14A	119.4
O2—C4—C3	116.11 (16)	C13—C14—H14A	119.4
C5—C4—C3	119.07 (18)	O4—C15—H15A	109.5
C4—C5—C6	120.71 (16)	O4—C15—H15B	109.5
C4—C5—H5A	119.6	H15A—C15—H15B	109.5
C6—C5—H5A	119.6	O4—C15—H15C	109.5
C5—C6—C1	119.36 (14)	H15A—C15—H15C	109.5
C5—C6—C7	118.83 (14)	H15B—C15—H15C	109.5
C1—C6—C7	121.80 (15)	O2—C16—H16A	109.5
N1—C7—C6	120.96 (14)	O2—C16—H16B	109.5
N1—C7—H7A	119.5	H16A—C16—H16B	109.5
C6—C7—H7A	119.5	O2—C16—H16C	109.5
O3—C8—N2	121.93 (14)	H16A—C16—H16C	109.5
O3—C8—C9	121.66 (14)	H16B—C16—H16C	109.5
N2—C8—C9	116.39 (12)
C7—N1—N2—C8	171.24 (14)	N1—N2—C8—O3	4.2 (2)
O1—C1—C2—C3	179.69 (17)	N1—N2—C8—C9	−177.33 (12)
C6—C1—C2—C3	−0.6 (3)	O3—C8—C9—C14	29.3 (2)
C1—C2—C3—C4	−0.4 (3)	N2—C8—C9—C14	−149.17 (14)
C16—O2—C4—C5	−6.0 (3)	O3—C8—C9—C10	−147.80 (16)
C16—O2—C4—C3	175.16 (18)	N2—C8—C9—C10	33.75 (19)
C2—C3—C4—O2	180.00 (17)	C15—O4—C10—C11	9.0 (2)
C2—C3—C4—C5	1.1 (3)	C15—O4—C10—C9	−174.19 (17)
O2—C4—C5—C6	−179.68 (15)	C14—C9—C10—O4	−173.55 (13)
C3—C4—C5—C6	−0.9 (3)	C8—C9—C10—O4	3.5 (2)
C4—C5—C6—C1	0.0 (2)	C14—C9—C10—C11	3.4 (2)
C4—C5—C6—C7	179.48 (14)	C8—C9—C10—C11	−179.56 (14)
O1—C1—C6—C5	−179.50 (15)	O4—C10—C11—C12	175.27 (16)
C2—C1—C6—C5	0.8 (2)	C9—C10—C11—C12	−1.4 (3)
O1—C1—C6—C7	1.0 (2)	C10—C11—C12—C13	−0.8 (3)
C2—C1—C6—C7	−178.75 (15)	C11—C12—C13—C14	0.9 (3)
N2—N1—C7—C6	−178.73 (13)	C10—C9—C14—C13	−3.3 (2)
C5—C6—C7—N1	173.93 (14)	C8—C9—C14—C13	179.48 (14)
C1—C6—C7—N1	−6.6 (2)	C12—C13—C14—C9	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.83 (2)	1.87 (2)	2.605 (2)	146.0 (19)
N2—H2A···O3i	0.835 (17)	2.051 (17)	2.8258 (17)	154.2 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.83 (2)	1.87 (2)	2.605 (2)	146.0 (19)
N2—H2A⋯O3i	0.835 (17)	2.051 (17)	2.8258 (17)	154.2 (15)

Symmetry code: (i) .