4-Meth­oxy-N′-(4-meth­oxy­benzyl­idene)benzohydrazide

Bi, Y.

doi:10.1107/S1600536811014012

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1182

doi:10.1107/S1600536811014012

Open

access

4-Methoxy-N′-(4-methoxybenzylidene)benzohydrazide

Ye Bi ^a ^*

^aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
^*Correspondence e-mail: biyeqqhar@yahoo.com.cn

(Received 6 April 2011; accepted 13 April 2011; online 22 April 2011)

The title compound, C₁₆H₁₆N₂O₃, was prepared by the reaction of 4-methoxybenzaldehyde with 4-methoxybenzohydrazide in methanol. The dihedral angle between the two benzene rings is 3.1 (3)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules 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_r = 284.31
Monoclinic, P c
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[F² > 2σ(F²)] = 0.059
wR(F²) = 0.138
S = 1.30
1396 reflections
195 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) x, y+1, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014012/cv5072sup1.cif

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

checkCIF report

Comment top

Hydrazone compounds have attracted much attention due to their biological activities (Peng, 2011; Angelusiu et al., 2010; Ajani et al., 2010; Horiuchi et al., 2009). In this paper, we present the title compound (I), which is a new hydrazone derivative.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds (Zhang, 2011; Lei & Fu, 2011; Tang, 2011). The dihedral angle between the two benzene rings is 3.1 (3)°. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along axis b into chains (Fig. 2).

Related literature top

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 top

Equimolar quantities (1.0 mmol each) of 4-methoxybenzaldehyde and 4-methoxybenzohydrazide were mixed in methanol. The mixture was stirred at room temperature for half an hour to give a colorless solution. After keeping the solution in air for a few days, colorless block-shaped crystals were formed.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A portion of the crystal packing viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines.

4-Methoxy-N'-(4-methoxybenzylidene)benzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₃	F(000) = 300
M_r = 284.31	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0182P)² + 0.6212P] where P = (F_o² + 2F_c²)/3
1396 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.24 e Å⁻³
3 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₃	V = 705.2 (4) Å³
M_r = 284.31	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 10.617 (3) Å	µ = 0.09 mm⁻¹
b = 4.877 (2) Å	T = 298 K
c = 13.632 (3) Å	0.20 × 0.18 × 0.17 mm
β = 92.409 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1396 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1026 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.984	R_int = 0.029
3893 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	3 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	Δρ_max = 0.24 e Å⁻³
1396 reflections	Δρ_min = −0.22 e Å⁻³
195 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₃
M_r	284.31
Crystal system, space group	Monoclinic, Pc
Temperature (K)	298
a, b, c (Å)	10.617 (3), 4.877 (2), 13.632 (3)
β (°)	92.409 (2)
V (Å³)	705.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.982, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	3893, 1396, 1026
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.138, 1.30
No. of reflections	1396
No. of parameters	195
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.900 (11)	1.99 (3)	2.844 (7)	157 (7)

Symmetry code: (i) x, y+1, z.

References

Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214–221. Web of Science CrossRef PubMed CAS Google Scholar
Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055–2062. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Horiuchi, T., Nagata, M., KitagawaB, M., Akahane, K. & Uoto, K. (2009). Bioorg. Med. Chem. 17, 7850–7860. Web of Science CrossRef PubMed CAS Google Scholar
Lei, Y. & Fu, C. (2011). Acta Cryst. E67, o410. Web of Science CSD CrossRef IUCr Journals Google Scholar
Peng, S.-J. (2011). J. Chem. Crystallogr. 41, 280-285. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, C.-B. (2011). Acta Cryst. E67, o271. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, Z. (2011). Acta Cryst. E67, o300. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1182

doi:10.1107/S1600536811014012

Open

access