N′-(2-Meth­oxy­benzyl­idene)-4-nitro­benzohydrazide

Zhu, H.-Y.

doi:10.1107/S1600536811008014

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o812

doi:10.1107/S1600536811008014

Open

access

N′-(2-Methoxybenzylidene)-4-nitrobenzohydrazide

Hai-Yun Zhu ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, People's Republic of China
^*Correspondence e-mail: zhuzhuhaiyun@126.com

(Received 2 March 2011; accepted 3 March 2011; online 9 March 2011)

The molecule of the title compound, C₁₅H₁₃N₃O₄, adopts an E configuration with respect to the C=N bond. The dihedral angle between the two benzene rings is 6.0 (3)°. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds to form chains along the c axis.

Related literature

For background on hydrazone compounds, see: Rasras et al. (2010 ); Fan et al. (2010 ); Ajani et al. (2010 ); Avaji et al. (2009 ). For the crystal structures of typical hydrazone compounds, see: Khaledi et al. (2010 ); Han et al. (2010 ); Hussain et al. (2010 ); Ji & Lu (2010 ). For the hydrazone compound reported recently by the author, see: Zhu (2010 ). For the reference bond values, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M_r = 299.28
Monoclinic, P 2₁ /c
a = 10.737 (2) Å
b = 14.728 (2) Å
c = 9.132 (1) Å
β = 93.572 (2)°
V = 1441.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.977, T_max = 0.980
9434 measured reflections
3129 independent reflections
1426 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.154
S = 0.99
3129 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.90 (1)	2.04 (1)	2.913 (3)	165 (2)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008014/sj5112sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008014/sj5112Isup2.hkl

checkCIF report

Comment top

In recent years, considerable attention has been focused on the preparation and biological properties of hydrazone compounds (Rasras et al., 2010; Fan et al., 2010; Ajani et al., 2010; Avaji et al., 2009). The crystal structures of a number of hydrazone compounds have been reported (Khaledi et al., 2010; Han et al., 2010; Hussain et al., 2010; Ji & Lu, 2010). As a continuation of the work on the structures of hydrazone compounds (Zhu, 2010), the author reports in this paper the title new hydrazone compound, Fig. 1.

The molecule of the compound adopts an E configuration with respect to the C═N bond. The dihedral angle between the C1—C6 and C10—C15 benzene rings is 6.0 (3)°. All the bond lengths are within normal values (Allen et al., 1987), and are comparable with those in the similar hydrazone compounds as cited above. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form chains along the c axis (Fig. 2).

Related literature top

For background on hydrazone compounds, see: Rasras et al. (2010); Fan et al. (2010); Ajani et al. (2010); Avaji et al. (2009). For the crystal structures of typical hydrazone compounds, see: Khaledi et al. (2010); Han et al. (2010); Hussain et al. (2010); Ji & Lu (2010). For the hydrazone compound reported recently by the author, see: Zhu (2010). For the reference bond values, see: Allen et al. (1987).

Experimental top

2-Methoxybenzaldehyde (0.136 g, 1 mmol) and 4-nitrobenzohydrazide (0.181 g, 1 mmol) were dissolved in 30 ml absolute methanol. The mixture was stirred at reflux for 10 min, and cooled to room temperature. The clear yellow solution was left to slow evaporation in air for 3 d, yielding yellow needle crystals of the compound.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 the title compound with 30% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. The molecular packing of the title compound. Hydrogen bonds are drawn as dashed lines.

N'-(2-Methoxybenzylidene)-4-nitrobenzohydrazide top

Crystal data top

C₁₅H₁₃N₃O₄	F(000) = 624
M_r = 299.28	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.737 (2) Å	Cell parameters from 864 reflections
b = 14.728 (2) Å	θ = 2.3–24.5°
c = 9.132 (1) Å	µ = 0.10 mm⁻¹
β = 93.572 (2)°	T = 298 K
V = 1441.3 (4) Å³	Cut from needle, yellow
Z = 4	0.23 × 0.21 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3129 independent reflections
Radiation source: fine-focus sealed tube	1426 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
T_min = 0.977, T_max = 0.980	k = −15→18
9434 measured reflections	l = −11→11

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0427P)²] where P = (F_o² + 2F_c²)/3
3129 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₄	V = 1441.3 (4) Å³
M_r = 299.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.737 (2) Å	µ = 0.10 mm⁻¹
b = 14.728 (2) Å	T = 298 K
c = 9.132 (1) Å	0.23 × 0.21 × 0.20 mm
β = 93.572 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3129 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1426 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.980	R_int = 0.077
9434 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.16 e Å⁻³
3129 reflections	Δρ_min = −0.20 e Å⁻³
203 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.30611 (19)	0.83021 (15)	1.0924 (2)	0.0485 (6)
N2	0.2592 (2)	0.75864 (15)	1.0066 (2)	0.0494 (6)
N3	0.0510 (2)	0.38411 (19)	0.7154 (3)	0.0661 (7)
O1	0.27693 (19)	1.07382 (12)	0.9099 (2)	0.0761 (7)
O2	0.22796 (17)	0.67342 (11)	1.2070 (2)	0.0597 (6)
O3	0.0703 (2)	0.30882 (15)	0.7635 (3)	0.1087 (10)
O4	−0.0029 (2)	0.39878 (16)	0.5963 (3)	0.0971 (8)
C1	0.3456 (2)	1.07183 (19)	1.0414 (3)	0.0539 (7)
C2	0.3634 (2)	0.98652 (18)	1.1036 (3)	0.0469 (7)
C3	0.4307 (2)	0.9800 (2)	1.2379 (3)	0.0612 (8)
H3	0.4428	0.9234	1.2817	0.073*
C4	0.4799 (3)	1.0566 (2)	1.3077 (4)	0.0776 (10)
H4	0.5248	1.0516	1.3977	0.093*
C5	0.4618 (3)	1.1399 (2)	1.2431 (4)	0.0752 (10)
H5	0.4958	1.1912	1.2896	0.090*
C6	0.3947 (3)	1.1492 (2)	1.1112 (4)	0.0695 (9)
H6	0.3821	1.2062	1.0691	0.083*
C7	0.2470 (4)	1.1582 (2)	0.8462 (4)	0.1186 (16)
H7A	0.2078	1.1957	0.9160	0.178*
H7B	0.1908	1.1496	0.7614	0.178*
H7C	0.3218	1.1872	0.8176	0.178*
C8	0.3139 (2)	0.90618 (17)	1.0267 (3)	0.0476 (7)
H8	0.2874	0.9105	0.9280	0.057*
C9	0.2221 (2)	0.68303 (17)	1.0733 (3)	0.0439 (6)
C10	0.1746 (2)	0.60759 (16)	0.9749 (3)	0.0408 (6)
C11	0.1895 (2)	0.51927 (17)	1.0271 (3)	0.0498 (7)
H11	0.2268	0.5096	1.1204	0.060*
C12	0.1499 (2)	0.44613 (18)	0.9432 (3)	0.0524 (7)
H12	0.1615	0.3871	0.9775	0.063*
C13	0.0927 (2)	0.46272 (17)	0.8069 (3)	0.0467 (7)
C14	0.0734 (2)	0.54826 (19)	0.7530 (3)	0.0507 (7)
H14	0.0332	0.5573	0.6610	0.061*
C15	0.1148 (2)	0.62158 (18)	0.8380 (3)	0.0492 (7)
H15	0.1023	0.6804	0.8029	0.059*
H2	0.251 (2)	0.7686 (17)	0.9092 (12)	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0614 (13)	0.0449 (13)	0.0394 (13)	−0.0007 (11)	0.0049 (11)	−0.0043 (12)
N2	0.0729 (15)	0.0427 (14)	0.0324 (12)	−0.0021 (11)	0.0011 (12)	−0.0001 (12)
N3	0.0642 (16)	0.0621 (18)	0.071 (2)	−0.0084 (13)	0.0000 (14)	−0.0067 (16)
O1	0.1061 (16)	0.0448 (13)	0.0748 (15)	0.0013 (11)	−0.0154 (13)	−0.0005 (11)
O2	0.0974 (15)	0.0493 (11)	0.0326 (11)	0.0034 (10)	0.0066 (10)	0.0039 (9)
O3	0.120 (2)	0.0480 (14)	0.151 (3)	0.0031 (13)	−0.0509 (18)	−0.0146 (16)
O4	0.140 (2)	0.0878 (18)	0.0610 (16)	−0.0348 (15)	−0.0160 (15)	−0.0079 (14)
C1	0.0560 (17)	0.0469 (18)	0.0589 (19)	−0.0005 (13)	0.0028 (15)	−0.0070 (15)
C2	0.0471 (15)	0.0471 (17)	0.0473 (17)	−0.0030 (12)	0.0094 (13)	−0.0101 (14)
C3	0.0607 (18)	0.062 (2)	0.061 (2)	−0.0022 (15)	0.0040 (16)	−0.0078 (16)
C4	0.069 (2)	0.088 (3)	0.074 (2)	−0.0099 (19)	−0.0092 (18)	−0.015 (2)
C5	0.0661 (19)	0.069 (2)	0.089 (3)	−0.0102 (17)	−0.0021 (19)	−0.031 (2)
C6	0.0653 (19)	0.0504 (19)	0.093 (3)	−0.0031 (15)	0.0068 (19)	−0.0135 (18)
C7	0.178 (4)	0.057 (2)	0.114 (3)	0.000 (2)	−0.052 (3)	0.016 (2)
C8	0.0585 (16)	0.0463 (16)	0.0385 (16)	0.0028 (13)	0.0077 (13)	−0.0005 (14)
C9	0.0539 (15)	0.0426 (16)	0.0358 (16)	0.0080 (12)	0.0070 (12)	0.0043 (14)
C10	0.0444 (14)	0.0433 (16)	0.0357 (15)	0.0039 (12)	0.0101 (12)	0.0044 (13)
C11	0.0588 (16)	0.0453 (17)	0.0449 (16)	0.0023 (13)	−0.0001 (13)	0.0058 (14)
C12	0.0585 (17)	0.0434 (16)	0.0551 (18)	0.0034 (13)	0.0015 (15)	0.0081 (15)
C13	0.0481 (15)	0.0426 (16)	0.0502 (17)	−0.0058 (12)	0.0089 (13)	−0.0046 (14)
C14	0.0591 (17)	0.0574 (18)	0.0356 (15)	−0.0037 (14)	0.0029 (13)	0.0050 (15)
C15	0.0632 (17)	0.0441 (16)	0.0402 (17)	0.0008 (13)	0.0017 (14)	0.0065 (14)

Geometric parameters (Å, º) top

N1—C8	1.275 (3)	C5—C6	1.371 (4)
N1—N2	1.389 (3)	C5—H5	0.9300
N2—C9	1.342 (3)	C6—H6	0.9300
N2—H2	0.900 (10)	C7—H7A	0.9600
N3—O3	1.206 (3)	C7—H7B	0.9600
N3—O4	1.219 (3)	C7—H7C	0.9600
N3—C13	1.480 (3)	C8—H8	0.9300
O1—C1	1.370 (3)	C9—C10	1.499 (3)
O1—C7	1.402 (3)	C10—C15	1.385 (3)
O2—C9	1.227 (3)	C10—C11	1.391 (3)
C1—C2	1.387 (4)	C11—C12	1.374 (3)
C1—C6	1.393 (4)	C11—H11	0.9300
C2—C3	1.387 (4)	C12—C13	1.375 (4)
C2—C8	1.460 (3)	C12—H12	0.9300
C3—C4	1.384 (4)	C13—C14	1.364 (3)
C3—H3	0.9300	C14—C15	1.387 (3)
C4—C5	1.369 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300

C8—N1—N2	115.6 (2)	H7A—C7—H7B	109.5
C9—N2—N1	118.7 (2)	O1—C7—H7C	109.5
C9—N2—H2	124.7 (16)	H7A—C7—H7C	109.5
N1—N2—H2	116.4 (17)	H7B—C7—H7C	109.5
O3—N3—O4	123.3 (3)	N1—C8—C2	121.1 (2)
O3—N3—C13	118.3 (3)	N1—C8—H8	119.4
O4—N3—C13	118.3 (3)	C2—C8—H8	119.4
C1—O1—C7	118.7 (2)	O2—C9—N2	123.3 (2)
O1—C1—C2	115.5 (2)	O2—C9—C10	120.4 (2)
O1—C1—C6	123.4 (3)	N2—C9—C10	116.3 (2)
C2—C1—C6	121.0 (3)	C15—C10—C11	119.0 (2)
C1—C2—C3	118.4 (3)	C15—C10—C9	123.5 (2)
C1—C2—C8	120.0 (3)	C11—C10—C9	117.4 (2)
C3—C2—C8	121.6 (3)	C12—C11—C10	121.2 (3)
C4—C3—C2	120.9 (3)	C12—C11—H11	119.4
C4—C3—H3	119.6	C10—C11—H11	119.4
C2—C3—H3	119.6	C11—C12—C13	118.1 (3)
C5—C4—C3	119.5 (3)	C11—C12—H12	121.0
C5—C4—H4	120.3	C13—C12—H12	121.0
C3—C4—H4	120.3	C14—C13—C12	122.7 (2)
C4—C5—C6	121.4 (3)	C14—C13—N3	119.0 (3)
C4—C5—H5	119.3	C12—C13—N3	118.3 (3)
C6—C5—H5	119.3	C13—C14—C15	118.8 (2)
C5—C6—C1	118.9 (3)	C13—C14—H14	120.6
C5—C6—H6	120.6	C15—C14—H14	120.6
C1—C6—H6	120.6	C10—C15—C14	120.3 (2)
O1—C7—H7A	109.5	C10—C15—H15	119.9
O1—C7—H7B	109.5	C14—C15—H15	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	2.04 (1)	2.913 (3)	165 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₄
M_r	299.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.737 (2), 14.728 (2), 9.132 (1)
β (°)	93.572 (2)
V (Å³)	1441.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.977, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	9434, 3129, 1426
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.154, 0.99
No. of reflections	3129
No. of parameters	203
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.900 (10)	2.035 (12)	2.913 (3)	165 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

This work was supported by the Science Research Foundation of Baoji University of Arts and Sciences (grant No. ZK085).

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
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Avaji, P. G., Kumar, C. H. V., Patil, S. A., Shivananda, K. N. & Nagaraju, C. (2009). Eur. J. Med. Chem. 44, 3552–3559. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fan, C. D., Su, H., Zhao, J., Zhao, B. X., Zhang, S. L. & Miao, J. Y. (2010). Eur. J. Med. Chem. 45, 1438–1446. Web of Science CrossRef CAS PubMed Google Scholar
Han, Y.-Y., Li, Y.-H. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1085–o1086. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hussain, A., Shafiq, Z., Tahir, M. N. & Yaqub, M. (2010). Acta Cryst. E66, o1888. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ji, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, o1514. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khaledi, H., Alhadi, A. A., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o105–o106. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rasras, A. J. M., Al-Tel, T. H., Amal, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307–2313. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, H.-Y. (2010). Acta Cryst. E66, o2562. Web of Science CSD CrossRef IUCr Journals Google Scholar