4-Meth-oxy-N'-(4-meth-oxy-benzyl-idene)benzohydrazide.

The title compound, C(16)H(16)N(2)O(3), was prepared by the reaction of 4-meth-oxy-benzaldehyde with 4-meth-oxy-benzohydrazide in methanol. The dihedral angle between the two benzene rings is 3.1 (3)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains along the b axis.

Related literature

For the biological activity of hydrazone compounds, see: Peng (2011 ▶); Angelusiu et al. (2010 ▶); Ajani et al. (2010 ▶); Horiuchi et al. (2009 ▶). For related structures, see: Zhang (2011 ▶); Lei & Fu (2011 ▶); Tang (2011 ▶).

Experimental

Crystal data

C16H16N2O3

M = 284.31

Monoclinic,

a = 10.617 (3) Å

b = 4.877 (2) Å

c = 13.632 (3) Å

β = 92.409 (2)°

V = 705.2 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.982, T max = 0.984

3893 measured reflections

1396 independent reflections

1026 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.138

S = 1.30

1396 reflections

195 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536811014012/cv5072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014012/cv5072Isup2.hkl

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

C16H16N2O3	F(000) = 300
Mr = 284.31	Dx = 1.339 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 10.617 (3) Å	Cell parameters from 1579 reflections
b = 4.877 (2) Å	θ = 2.9–28.3°
c = 13.632 (3) Å	µ = 0.09 mm−1
β = 92.409 (2)°	T = 298 K
V = 705.2 (4) Å3	Block, colourless
Z = 2	0.20 × 0.18 × 0.17 mm

Bruker SMART 1000 CCD area-detector diffractometer	1396 independent reflections
Radiation source: fine-focus sealed tube	1026 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 26.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.982, Tmax = 0.984	k = −6→6
3893 measured reflections	l = −16→17

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	w = 1/[σ2(Fo2) + (0.0182P)2 + 0.6212P] where P = (Fo2 + 2Fc2)/3
1396 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.24 e Å−3
3 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.4613 (6)	0.2010 (11)	0.6226 (5)	0.0425 (15)
N2	0.5326 (7)	0.2629 (11)	0.5429 (5)	0.0450 (16)
O1	0.1067 (5)	0.2188 (12)	0.9836 (4)	0.0622 (17)
O2	0.5985 (5)	−0.1728 (8)	0.5324 (4)	0.0565 (13)
O3	0.8991 (5)	0.3171 (14)	0.1869 (4)	0.0609 (16)
C1	0.3252 (7)	0.3481 (14)	0.7438 (6)	0.0426 (19)
C2	0.3588 (7)	0.1499 (17)	0.8117 (6)	0.051 (2)
H2	0.4308	0.0462	0.8022	0.061*
C3	0.2908 (7)	0.0991 (17)	0.8929 (6)	0.056 (2)
H3	0.3165	−0.0343	0.9381	0.067*
C4	0.1832 (8)	0.2503 (16)	0.9059 (6)	0.048 (2)
C5	0.1462 (9)	0.4446 (17)	0.8393 (6)	0.063 (3)
H5	0.0728	0.5442	0.8479	0.076*
C6	0.2175 (9)	0.4938 (16)	0.7594 (7)	0.063 (3)
H6	0.1920	0.6292	0.7148	0.075*
C7	0.3991 (8)	0.3890 (13)	0.6570 (6)	0.046 (2)
H7	0.3992	0.5602	0.6269	0.056*
C8	0.1325 (10)	0.0017 (19)	1.0495 (7)	0.073 (3)
H8A	0.1294	−0.1691	1.0144	0.110*
H8B	0.0708	0.0002	1.0990	0.110*
H8C	0.2150	0.0258	1.0799	0.110*
C9	0.6006 (7)	0.0565 (13)	0.5037 (5)	0.0379 (17)
C10	0.6766 (6)	0.1469 (14)	0.4199 (5)	0.0358 (16)
C11	0.7875 (7)	0.0084 (14)	0.4050 (6)	0.046 (2)
H11	0.8132	−0.1311	0.4478	0.055*
C12	0.8599 (8)	0.0742 (16)	0.3281 (6)	0.051 (2)
H12	0.9361	−0.0157	0.3203	0.061*
C13	0.8211 (8)	0.2711 (15)	0.2624 (6)	0.0434 (18)
C14	0.7112 (7)	0.4090 (14)	0.2749 (5)	0.046 (2)
H14	0.6848	0.5440	0.2305	0.055*
C15	0.6390 (7)	0.3463 (15)	0.3546 (5)	0.0427 (18)
H15	0.5644	0.4409	0.3635	0.051*
C16	0.8644 (10)	0.5240 (18)	0.1176 (6)	0.062 (3)
H16A	0.7837	0.4805	0.0870	0.093*
H16B	0.9263	0.5338	0.0684	0.093*
H16C	0.8596	0.6976	0.1504	0.093*
H2A	0.539 (8)	0.440 (5)	0.525 (6)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.047 (4)	0.024 (3)	0.058 (4)	−0.002 (3)	0.015 (3)	−0.002 (3)
N2	0.045 (4)	0.040 (3)	0.052 (4)	−0.006 (3)	0.017 (3)	0.010 (3)
O1	0.055 (4)	0.071 (4)	0.062 (4)	0.008 (3)	0.025 (3)	0.005 (3)
O2	0.077 (3)	0.018 (2)	0.077 (3)	−0.002 (2)	0.027 (3)	0.007 (2)
O3	0.049 (4)	0.081 (4)	0.054 (3)	−0.001 (3)	0.016 (3)	0.008 (3)
C1	0.049 (5)	0.019 (3)	0.060 (5)	0.006 (3)	0.006 (4)	−0.002 (3)
C2	0.040 (5)	0.053 (5)	0.061 (5)	0.009 (4)	0.014 (4)	0.008 (4)
C3	0.043 (5)	0.066 (5)	0.060 (6)	0.012 (5)	0.005 (5)	0.013 (4)
C4	0.037 (4)	0.061 (5)	0.047 (5)	−0.004 (4)	0.006 (4)	−0.004 (4)
C5	0.056 (6)	0.063 (6)	0.071 (7)	0.026 (5)	0.017 (5)	0.009 (5)
C6	0.080 (7)	0.047 (5)	0.063 (6)	0.017 (5)	0.019 (6)	0.017 (4)
C7	0.061 (5)	0.016 (3)	0.063 (5)	−0.003 (3)	0.014 (4)	0.012 (3)
C8	0.085 (8)	0.072 (6)	0.066 (7)	−0.002 (5)	0.030 (6)	0.004 (5)
C9	0.031 (4)	0.038 (4)	0.045 (4)	−0.004 (3)	0.004 (3)	−0.007 (3)
C10	0.031 (4)	0.034 (3)	0.043 (4)	−0.010 (3)	0.006 (3)	0.000 (3)
C11	0.040 (5)	0.039 (4)	0.060 (6)	0.004 (3)	0.006 (4)	0.007 (4)
C12	0.038 (5)	0.058 (5)	0.057 (6)	0.010 (4)	0.009 (4)	−0.002 (4)
C13	0.039 (4)	0.042 (4)	0.050 (5)	−0.007 (3)	0.007 (4)	−0.007 (3)
C14	0.054 (5)	0.042 (4)	0.043 (5)	0.001 (4)	0.012 (4)	0.007 (3)
C15	0.037 (4)	0.038 (4)	0.054 (5)	0.007 (4)	0.005 (4)	0.001 (4)
C16	0.072 (7)	0.067 (5)	0.049 (5)	−0.011 (5)	0.017 (5)	0.003 (4)

N1—C7	1.234 (9)	C6—H6	0.9300
N1—N2	1.383 (6)	C7—H7	0.9300
N2—C9	1.361 (9)	C8—H8A	0.9600
N2—H2A	0.900 (11)	C8—H8B	0.9600
O1—C4	1.371 (10)	C8—H8C	0.9600
O1—C8	1.408 (10)	C9—C10	1.492 (9)
O2—C9	1.186 (7)	C10—C15	1.367 (9)
O3—C13	1.366 (10)	C10—C11	1.380 (10)
O3—C16	1.421 (10)	C11—C12	1.364 (10)
C1—C6	1.370 (11)	C11—H11	0.9300
C1—C2	1.375 (10)	C12—C13	1.365 (11)
C1—C7	1.462 (10)	C12—H12	0.9300
C2—C3	1.369 (11)	C13—C14	1.364 (11)
C2—H2	0.9300	C14—C15	1.390 (10)
C3—C4	1.377 (11)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.359 (11)	C16—H16A	0.9600
C5—C6	1.373 (11)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C7—N1—N2	117.1 (6)	O1—C8—H8C	109.5
C9—N2—N1	117.6 (5)	H8A—C8—H8C	109.5
C9—N2—H2A	124 (5)	H8B—C8—H8C	109.5
N1—N2—H2A	118 (5)	O2—C9—N2	123.4 (7)
C4—O1—C8	118.1 (7)	O2—C9—C10	123.4 (7)
C13—O3—C16	118.0 (7)	N2—C9—C10	113.2 (6)
C6—C1—C2	117.1 (8)	C15—C10—C11	118.6 (7)
C6—C1—C7	122.3 (7)	C15—C10—C9	123.9 (6)
C2—C1—C7	120.5 (7)	C11—C10—C9	117.4 (7)
C3—C2—C1	122.7 (7)	C12—C11—C10	120.6 (7)
C3—C2—H2	118.7	C12—C11—H11	119.7
C1—C2—H2	118.7	C10—C11—H11	119.7
C2—C3—C4	118.4 (8)	C11—C12—C13	120.4 (8)
C2—C3—H3	120.8	C11—C12—H12	119.8
C4—C3—H3	120.8	C13—C12—H12	119.8
C5—C4—O1	115.5 (8)	C14—C13—C12	120.0 (8)
C5—C4—C3	120.4 (9)	C14—C13—O3	124.2 (7)
O1—C4—C3	124.1 (8)	C12—C13—O3	115.7 (8)
C4—C5—C6	119.9 (8)	C13—C14—C15	119.5 (7)
C4—C5—H5	120.1	C13—C14—H14	120.3
C6—C5—H5	120.1	C15—C14—H14	120.3
C1—C6—C5	121.6 (8)	C10—C15—C14	120.7 (7)
C1—C6—H6	119.2	C10—C15—H15	119.6
C5—C6—H6	119.2	C14—C15—H15	119.6
N1—C7—C1	121.4 (6)	O3—C16—H16A	109.5
N1—C7—H7	119.3	O3—C16—H16B	109.5
C1—C7—H7	119.3	H16A—C16—H16B	109.5
O1—C8—H8A	109.5	O3—C16—H16C	109.5
O1—C8—H8B	109.5	H16A—C16—H16C	109.5
H8A—C8—H8B	109.5	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.90 (1)	1.99 (3)	2.844 (7)	157 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.90 (1)	1.99 (3)	2.844 (7)	157 (7)

Symmetry code: (i) .