(E)-N′-(4-Meth­oxy­benzyl­idene)-3-nitro­benzohydrazide

Guo, J.-W.; Ma, J.-Y.; Sun, C.-W.

doi:10.1107/S1600536811025554

organic compounds

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Volume 67| Part 8| August 2011| Page o1886

doi:10.1107/S1600536811025554

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(E)-N′-(4-Methoxybenzylidene)-3-nitrobenzohydrazide

Jin-Wu Guo,^a Jun-Ying Ma ^a ^* and Chao-Wei Sun ^a

^aChemical Engineering & Pharmaceutics College, Henan University of Science and Technology, Luoyang Henan 471003, People's Republic of China
^*Correspondence e-mail: junying_ma@163.com

(Received 22 June 2011; accepted 28 June 2011; online 2 July 2011)

In the title compound, C₁₅H₁₃N₃O₄, the two substituted benzene rings form a dihedral angle of 5.0 (3)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link molecules into chains along the b axis.

Related literature

For background to the binding properties and biological activity of condensation products of aldehydes with benzohydrazides, see: Sanchez-Lozano et al. (2011 ); Wang (2011 ); Cui et al. (2011 ); Zhu (2011 ); Peng (2011 ). For related structures, see: Hashemian et al. (2011 ); Shalash et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M_r = 299.28
Monoclinic, P 2₁ /c
a = 13.667 (4) Å
b = 4.889 (3) Å
c = 22.522 (4) Å
β = 104.113 (3)°
V = 1459.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.970, T_max = 0.973
9043 measured reflections
2981 independent reflections
1493 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.173
S = 1.02
2981 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.13	2.895 (3)	148
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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/S1600536811025554/rz2619sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025554/rz2619Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025554/rz2619Isup3.cml

checkCIF report

Comment top

The compounds derived from the condensation reaction of aldehydes with benzohydrazides play a vital role in coordination chemistry due to their metal binding property (Sanchez-Lozano et al., 2011; Wang, 2011; Cui et al., 2011). Moreover, most of such compounds possess effective biological activity (Zhu, 2011; Peng, 2011). In recent years, a number of such compounds have been reported (Hashemian et al., 2011; Shalash et al., 2010). In this paper, the title new compound, (E)-N'-(4-Methoxybenzylidene)-3-nitrobenzohydrazide, (I), is reported.

The molecular structure of (I) is shown in Fig. 1. The bond lengths in (I) are normal and comparable with those observed in the reported structures cited above. The two substituted benzene rings form a dihedral angle of 5.0 (3)°. In the crystal, intermolecular N–H···O hydrogen bonds link molecules into one-dimensional chains along the b axis (Fig. 2; Table 1).

Related literature top

For background to the binding properties and biological activity of condensation products of aldehydes with benzohydrazides, see: Sanchez-Lozano et al. (2011); Wang (2011); Cui et al. (2011); Zhu (2011); Peng (2011). For related structures, see: Hashemian et al. (2011); Shalash et al. (2010).

Experimental top

4-Methoxybenzaldehyde (0.136 g, 1 mmol), 3-nitrobenzohydrazide (0.181 g, 1 mmol), and a few drops of acetic acid were mixed in methanol (30 ml). The solution was magnetically stirred at ambient temperature for 10 min until it turned to yellow. The solution was slowly evaporated in open air to give needle-shaped pale yellow single crystals.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 the title compound with displacement ellipsoids shown at 30% probability level.
	Fig. 2. Packing diagram of the title compound, viewed along the c axis. Hydrogen bonds are indicated by dashed lines.

(E)-N'-(4-Methoxybenzylidene)-3-nitrobenzohydrazide top

Crystal data top

C₁₅H₁₃N₃O₄	F(000) = 624
M_r = 299.28	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 762 reflections
a = 13.667 (4) Å	θ = 2.6–24.3°
b = 4.889 (3) Å	µ = 0.10 mm⁻¹
c = 22.522 (4) Å	T = 298 K
β = 104.113 (3)°	Needle fragment, pale yellow
V = 1459.5 (10) Å³	0.30 × 0.28 × 0.27 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2981 independent reflections
Radiation source: fine-focus sealed tube	1493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −16→16
T_min = 0.970, T_max = 0.973	k = −6→6
9043 measured reflections	l = −28→28

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
2981 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₄	V = 1459.5 (10) Å³
M_r = 299.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.667 (4) Å	µ = 0.10 mm⁻¹
b = 4.889 (3) Å	T = 298 K
c = 22.522 (4) Å	0.30 × 0.28 × 0.27 mm
β = 104.113 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2981 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1493 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.973	R_int = 0.073
9043 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
2981 reflections	Δρ_min = −0.26 e Å⁻³
200 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	0.26856 (19)	0.4077 (5)	0.12291 (10)	0.0478 (7)
N2	0.22236 (19)	0.4793 (4)	0.06262 (10)	0.0481 (7)
H2A	0.2022	0.6443	0.0537	0.058*
N3	−0.03766 (19)	0.8680 (5)	−0.13175 (12)	0.0519 (7)
O1	0.44934 (18)	0.4662 (5)	0.41484 (9)	0.0673 (7)
O2	0.23532 (17)	0.0453 (4)	0.02765 (9)	0.0572 (6)
O3	−0.05412 (17)	0.9975 (4)	−0.08818 (10)	0.0658 (7)
O4	−0.08122 (19)	0.9108 (5)	−0.18561 (10)	0.0813 (8)
C1	0.3188 (2)	0.5554 (6)	0.22758 (11)	0.0425 (7)
C2	0.3912 (2)	0.3558 (6)	0.24755 (12)	0.0486 (8)
H2	0.4092	0.2423	0.2188	0.058*
C3	0.4377 (2)	0.3199 (6)	0.30896 (12)	0.0501 (8)
H3A	0.4870	0.1862	0.3210	0.060*
C4	0.4100 (2)	0.4862 (6)	0.35258 (12)	0.0467 (8)
C5	0.3381 (3)	0.6875 (6)	0.33375 (13)	0.0543 (9)
H5	0.3197	0.7990	0.3627	0.065*
C6	0.2933 (2)	0.7246 (6)	0.27212 (12)	0.0510 (8)
H6	0.2459	0.8628	0.2600	0.061*
C7	0.2695 (2)	0.5983 (6)	0.16229 (12)	0.0470 (8)
H7	0.2388	0.7651	0.1495	0.056*
C8	0.2095 (2)	0.2863 (6)	0.01832 (12)	0.0417 (7)
C9	0.1590 (2)	0.3825 (5)	−0.04553 (11)	0.0399 (7)
C10	0.0857 (2)	0.5890 (5)	−0.05782 (12)	0.0410 (7)
H10	0.0681	0.6832	−0.0261	0.049*
C11	0.0400 (2)	0.6497 (6)	−0.11841 (12)	0.0421 (7)
C12	0.0651 (3)	0.5157 (6)	−0.16723 (13)	0.0523 (8)
H12	0.0331	0.5608	−0.2074	0.063*
C13	0.1384 (2)	0.3145 (6)	−0.15503 (12)	0.0541 (9)
H13	0.1569	0.2247	−0.1870	0.065*
C14	0.1841 (2)	0.2474 (6)	−0.09470 (12)	0.0492 (8)
H14	0.2324	0.1096	−0.0868	0.059*
C15	0.5296 (3)	0.2752 (9)	0.43634 (14)	0.0875 (12)
H15A	0.5063	0.0935	0.4243	0.131*
H15B	0.5512	0.2849	0.4802	0.131*
H15C	0.5852	0.3190	0.4189	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0634 (18)	0.0364 (15)	0.0395 (13)	0.0020 (13)	0.0045 (12)	0.0084 (11)
N2	0.0673 (19)	0.0320 (14)	0.0397 (14)	0.0072 (13)	0.0030 (12)	0.0094 (10)
N3	0.0450 (17)	0.0560 (18)	0.0523 (17)	−0.0011 (14)	0.0073 (13)	0.0085 (13)
O1	0.0695 (17)	0.0890 (18)	0.0390 (12)	0.0124 (14)	0.0046 (11)	−0.0008 (11)
O2	0.0809 (17)	0.0307 (12)	0.0582 (13)	0.0075 (11)	0.0133 (12)	0.0063 (9)
O3	0.0615 (16)	0.0655 (16)	0.0698 (15)	0.0145 (12)	0.0146 (13)	0.0037 (12)
O4	0.0762 (19)	0.105 (2)	0.0522 (14)	0.0205 (15)	−0.0048 (13)	0.0249 (13)
C1	0.050 (2)	0.0380 (18)	0.0387 (16)	−0.0020 (15)	0.0093 (14)	0.0047 (12)
C2	0.062 (2)	0.0399 (18)	0.0441 (17)	0.0041 (16)	0.0133 (15)	−0.0018 (13)
C3	0.055 (2)	0.052 (2)	0.0405 (16)	0.0077 (16)	0.0058 (14)	0.0046 (14)
C4	0.047 (2)	0.051 (2)	0.0394 (17)	−0.0044 (16)	0.0072 (14)	0.0016 (13)
C5	0.068 (2)	0.054 (2)	0.0424 (17)	0.0057 (18)	0.0169 (16)	−0.0048 (14)
C6	0.054 (2)	0.0454 (19)	0.0536 (18)	0.0073 (16)	0.0128 (15)	0.0032 (14)
C7	0.059 (2)	0.0365 (18)	0.0443 (17)	0.0038 (16)	0.0107 (15)	0.0060 (13)
C8	0.0498 (19)	0.0344 (18)	0.0416 (15)	0.0004 (15)	0.0123 (14)	0.0039 (13)
C9	0.0529 (19)	0.0271 (15)	0.0400 (15)	−0.0051 (14)	0.0118 (14)	0.0011 (12)
C10	0.0461 (19)	0.0353 (17)	0.0417 (16)	−0.0040 (14)	0.0109 (14)	0.0007 (12)
C11	0.0452 (19)	0.0382 (17)	0.0411 (16)	−0.0049 (15)	0.0070 (14)	0.0064 (12)
C12	0.060 (2)	0.057 (2)	0.0356 (16)	−0.0111 (18)	0.0034 (15)	0.0027 (14)
C13	0.070 (2)	0.053 (2)	0.0422 (17)	−0.0027 (18)	0.0203 (16)	−0.0022 (15)
C14	0.057 (2)	0.0402 (19)	0.0511 (18)	−0.0007 (16)	0.0152 (15)	0.0005 (14)
C15	0.093 (3)	0.105 (3)	0.049 (2)	0.024 (3)	−0.013 (2)	0.001 (2)

Geometric parameters (Å, º) top

N1—C7	1.284 (3)	C5—C6	1.386 (4)
N1—N2	1.395 (3)	C5—H5	0.9300
N2—C8	1.353 (3)	C6—H6	0.9300
N2—H2A	0.8600	C7—H7	0.9300
N3—O4	1.232 (3)	C8—C9	1.510 (4)
N3—O3	1.234 (3)	C9—C14	1.402 (3)
N3—C11	1.483 (4)	C9—C10	1.402 (4)
O1—C4	1.377 (3)	C10—C11	1.387 (3)
O1—C15	1.432 (4)	C10—H10	0.9300
O2—C8	1.233 (3)	C11—C12	1.393 (4)
C1—C2	1.385 (4)	C12—C13	1.383 (4)
C1—C6	1.408 (4)	C12—H12	0.9300
C1—C7	1.475 (4)	C13—C14	1.389 (4)
C2—C3	1.385 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.397 (4)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.382 (4)	C15—H15C	0.9600

C7—N1—N2	114.6 (2)	C1—C7—H7	119.7
C8—N2—N1	119.3 (2)	O2—C8—N2	124.1 (2)
C8—N2—H2A	120.4	O2—C8—C9	120.3 (2)
N1—N2—H2A	120.4	N2—C8—C9	115.6 (2)
O4—N3—O3	123.9 (3)	C14—C9—C10	118.9 (2)
O4—N3—C11	118.1 (3)	C14—C9—C8	117.6 (3)
O3—N3—C11	117.9 (2)	C10—C9—C8	123.4 (2)
C4—O1—C15	117.8 (2)	C11—C10—C9	118.5 (3)
C2—C1—C6	117.6 (2)	C11—C10—H10	120.8
C2—C1—C7	122.7 (3)	C9—C10—H10	120.8
C6—C1—C7	119.6 (3)	C10—C11—C12	122.5 (3)
C1—C2—C3	122.1 (3)	C10—C11—N3	118.8 (3)
C1—C2—H2	119.0	C12—C11—N3	118.7 (3)
C3—C2—H2	119.0	C13—C12—C11	118.9 (3)
C2—C3—C4	119.4 (3)	C13—C12—H12	120.5
C2—C3—H3A	120.3	C11—C12—H12	120.5
C4—C3—H3A	120.3	C12—C13—C14	119.6 (3)
O1—C4—C5	115.8 (3)	C12—C13—H13	120.2
O1—C4—C3	124.7 (3)	C14—C13—H13	120.2
C5—C4—C3	119.5 (3)	C13—C14—C9	121.5 (3)
C4—C5—C6	120.5 (3)	C13—C14—H14	119.2
C4—C5—H5	119.7	C9—C14—H14	119.2
C6—C5—H5	119.7	O1—C15—H15A	109.5
C5—C6—C1	120.7 (3)	O1—C15—H15B	109.5
C5—C6—H6	119.6	H15A—C15—H15B	109.5
C1—C6—H6	119.6	O1—C15—H15C	109.5
N1—C7—C1	120.7 (3)	H15A—C15—H15C	109.5
N1—C7—H7	119.7	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.13	2.895 (3)	148

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

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)	13.667 (4), 4.889 (3), 22.522 (4)
β (°)	104.113 (3)
V (Å³)	1459.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.28 × 0.27

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.970, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	9043, 2981, 1493
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.173, 1.02
No. of reflections	2981
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.26

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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	0.86	2.13	2.895 (3)	148

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

Acknowledgements

Financial support from Henan University of Science and Technology is gratefully acknowledged.

References

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