(E)-N′-(2-Meth­oxy­benzyl­idene)-3-nitro­benzohydrazide

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

doi:10.1107/S1600536811025542

organic compounds

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Volume 67| Part 8| August 2011| Page o1895

doi:10.1107/S1600536811025542

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(E)-N′-(2-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 10.9 (3)°. In the crystal, intermolecular C—H⋯O and N—H⋯O hydrogen bonds link molecules into chains running parallel to [101].

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 /n
a = 6.9886 (13) Å
b = 29.543 (3) Å
c = 7.4163 (14) Å
β = 109.229 (2)°
V = 1445.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.17 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.980, T_max = 0.987
11773 measured reflections
3140 independent reflections
1547 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.160
S = 1.02
3140 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.27 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	0.86	2.03	2.856 (3)	162
C8—H8⋯O2ⁱ	0.93	2.47	3.231 (3)	139
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: 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/S1600536811025542/rz2618sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025542/rz2618Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025542/rz2618Isup3.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 comound, (E)-N'-(2-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 10.9 (3)°. In the crystal, intermolecular C–H···O and N–H···O hydrogen bonds link molecules into one-dimensional chains parallel to the [101] direction (Fig. 2, Table 1).

Related literature top

For background to the binding properties and biological activity of the 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

2-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 magnetic stirred at ambient temperature for 10 min until it turns 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'-(2-Methoxybenzylidene)-3-nitrobenzohydrazide top

Crystal data top

C₁₅H₁₃N₃O₄	F(000) = 624
M_r = 299.28	D_x = 1.375 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1029 reflections
a = 6.9886 (13) Å	θ = 2.7–24.6°
b = 29.543 (3) Å	µ = 0.10 mm⁻¹
c = 7.4163 (14) Å	T = 298 K
β = 109.229 (2)°	Needle fragment, pale yellow
V = 1445.8 (4) Å³	0.20 × 0.17 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3140 independent reflections
Radiation source: fine-focus sealed tube	1547 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scans	θ_max = 27.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→8
T_min = 0.980, T_max = 0.987	k = −37→37
11773 measured reflections	l = −9→9

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0565P)² + 0.2817P] where P = (F_o² + 2F_c²)/3
3140 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₄	V = 1445.8 (4) Å³
M_r = 299.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9886 (13) Å	µ = 0.10 mm⁻¹
b = 29.543 (3) Å	T = 298 K
c = 7.4163 (14) Å	0.20 × 0.17 × 0.13 mm
β = 109.229 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3140 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1547 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.987	R_int = 0.066
11773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
3140 reflections	Δρ_min = −0.20 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	0.1106 (3)	0.28532 (7)	0.7046 (3)	0.0472 (6)
N2	0.1501 (3)	0.25598 (7)	0.8592 (3)	0.0484 (6)
H2	0.2305	0.2639	0.9698	0.058*
N3	0.1869 (5)	0.06220 (10)	1.1044 (6)	0.0779 (10)
O1	0.2305 (4)	0.41464 (7)	0.8421 (3)	0.0717 (7)
O2	−0.0564 (3)	0.20220 (6)	0.6790 (3)	0.0594 (6)
O3	0.1521 (5)	0.04907 (9)	0.9404 (5)	0.1073 (11)
O4	0.2330 (5)	0.03803 (9)	1.2447 (5)	0.1236 (12)
C1	0.1507 (4)	0.35973 (8)	0.6012 (4)	0.0422 (7)
C2	0.1822 (4)	0.40543 (9)	0.6509 (5)	0.0521 (8)
C3	0.1630 (5)	0.43806 (11)	0.5128 (6)	0.0696 (10)
H3	0.1813	0.4685	0.5463	0.084*
C4	0.1166 (5)	0.42509 (13)	0.3260 (6)	0.0775 (11)
H4	0.1030	0.4471	0.2329	0.093*
C5	0.0895 (5)	0.38036 (13)	0.2730 (5)	0.0694 (10)
H5	0.0613	0.3720	0.1460	0.083*
C6	0.1050 (4)	0.34806 (10)	0.4110 (4)	0.0534 (8)
H6	0.0843	0.3178	0.3756	0.064*
C7	0.2868 (6)	0.45963 (11)	0.9068 (6)	0.0987 (14)
H7A	0.3885	0.4703	0.8561	0.148*
H7B	0.3399	0.4600	1.0438	0.148*
H7C	0.1701	0.4790	0.8641	0.148*
C8	0.1739 (4)	0.32553 (9)	0.7488 (4)	0.0438 (7)
H8	0.2356	0.3332	0.8765	0.053*
C9	0.0617 (4)	0.21543 (9)	0.8337 (4)	0.0424 (7)
C10	0.1119 (4)	0.18579 (9)	1.0065 (4)	0.0408 (7)
C11	0.1229 (4)	0.13972 (9)	0.9798 (4)	0.0471 (7)
H11	0.1008	0.1281	0.8580	0.057*
C12	0.1664 (4)	0.11134 (10)	1.1332 (5)	0.0555 (8)
C13	0.1935 (5)	0.12710 (13)	1.3129 (5)	0.0705 (10)
H13	0.2224	0.1071	1.4152	0.085*
C14	0.1779 (5)	0.17262 (13)	1.3418 (4)	0.0679 (10)
H14	0.1927	0.1836	1.4632	0.082*
C15	0.1397 (4)	0.20246 (10)	1.1875 (4)	0.0519 (8)
H15	0.1331	0.2335	1.2066	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0486 (15)	0.0407 (13)	0.0443 (14)	−0.0023 (11)	0.0043 (11)	0.0050 (11)
N2	0.0522 (15)	0.0401 (13)	0.0404 (13)	−0.0071 (11)	−0.0018 (11)	0.0035 (11)
N3	0.058 (2)	0.053 (2)	0.120 (3)	0.0095 (15)	0.026 (2)	0.032 (2)
O1	0.0983 (19)	0.0453 (13)	0.0778 (16)	−0.0138 (12)	0.0374 (14)	−0.0101 (11)
O2	0.0711 (15)	0.0427 (11)	0.0449 (12)	−0.0095 (10)	−0.0074 (10)	0.0009 (9)
O3	0.120 (3)	0.0580 (17)	0.148 (3)	0.0149 (16)	0.051 (2)	0.0044 (18)
O4	0.118 (3)	0.0780 (19)	0.170 (3)	0.0217 (17)	0.040 (2)	0.071 (2)
C1	0.0329 (16)	0.0424 (16)	0.0473 (17)	−0.0009 (12)	0.0080 (13)	0.0055 (13)
C2	0.0479 (19)	0.0468 (18)	0.063 (2)	−0.0025 (14)	0.0205 (16)	0.0043 (15)
C3	0.069 (2)	0.051 (2)	0.092 (3)	0.0039 (17)	0.030 (2)	0.0190 (19)
C4	0.074 (3)	0.078 (3)	0.082 (3)	0.012 (2)	0.026 (2)	0.037 (2)
C5	0.064 (2)	0.089 (3)	0.052 (2)	0.010 (2)	0.0146 (17)	0.0144 (19)
C6	0.0457 (19)	0.0603 (19)	0.0484 (18)	0.0025 (15)	0.0076 (14)	0.0078 (15)
C7	0.132 (4)	0.062 (2)	0.120 (3)	−0.031 (2)	0.065 (3)	−0.037 (2)
C8	0.0397 (17)	0.0452 (17)	0.0424 (16)	0.0018 (13)	0.0081 (13)	0.0014 (13)
C9	0.0427 (18)	0.0387 (15)	0.0400 (16)	0.0026 (13)	0.0056 (14)	−0.0001 (12)
C10	0.0312 (16)	0.0437 (16)	0.0414 (16)	−0.0002 (12)	0.0037 (12)	0.0041 (13)
C11	0.0372 (17)	0.0478 (18)	0.0529 (18)	0.0002 (13)	0.0102 (14)	0.0055 (14)
C12	0.0377 (18)	0.0513 (19)	0.074 (2)	0.0027 (14)	0.0143 (16)	0.0158 (17)
C13	0.053 (2)	0.078 (3)	0.071 (3)	−0.0061 (18)	0.0075 (18)	0.034 (2)
C14	0.059 (2)	0.099 (3)	0.0434 (18)	−0.014 (2)	0.0130 (16)	0.0054 (18)
C15	0.0441 (19)	0.0610 (19)	0.0466 (17)	−0.0066 (14)	0.0096 (14)	−0.0014 (15)

Geometric parameters (Å, º) top

N1—C8	1.272 (3)	C5—C6	1.377 (4)
N1—N2	1.390 (3)	C5—H5	0.9300
N2—C9	1.332 (3)	C6—H6	0.9300
N2—H2	0.8600	C7—H7A	0.9600
N3—O4	1.215 (4)	C7—H7B	0.9600
N3—O3	1.223 (4)	C7—H7C	0.9600
N3—C12	1.481 (4)	C8—H8	0.9300
O1—C2	1.373 (3)	C9—C10	1.496 (3)
O1—C7	1.424 (3)	C10—C11	1.381 (4)
O2—C9	1.235 (3)	C10—C15	1.382 (4)
C1—C6	1.384 (4)	C11—C12	1.364 (4)
C1—C2	1.397 (4)	C11—H11	0.9300
C1—C8	1.459 (3)	C12—C13	1.365 (4)
C2—C3	1.380 (4)	C13—C14	1.372 (4)
C3—C4	1.369 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.399 (4)
C4—C5	1.374 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300

C8—N1—N2	114.3 (2)	H7A—C7—H7B	109.5
C9—N2—N1	119.1 (2)	O1—C7—H7C	109.5
C9—N2—H2	120.4	H7A—C7—H7C	109.5
N1—N2—H2	120.4	H7B—C7—H7C	109.5
O4—N3—O3	125.1 (4)	N1—C8—C1	120.7 (2)
O4—N3—C12	117.6 (4)	N1—C8—H8	119.7
O3—N3—C12	117.2 (3)	C1—C8—H8	119.7
C2—O1—C7	118.7 (3)	O2—C9—N2	123.6 (2)
C6—C1—C2	118.2 (3)	O2—C9—C10	120.4 (2)
C6—C1—C8	121.6 (2)	N2—C9—C10	116.0 (2)
C2—C1—C8	120.2 (3)	C11—C10—C15	119.6 (3)
O1—C2—C3	124.0 (3)	C11—C10—C9	117.6 (2)
O1—C2—C1	115.3 (2)	C15—C10—C9	122.8 (2)
C3—C2—C1	120.7 (3)	C12—C11—C10	119.6 (3)
C4—C3—C2	119.2 (3)	C12—C11—H11	120.2
C4—C3—H3	120.4	C10—C11—H11	120.2
C2—C3—H3	120.4	C11—C12—C13	121.7 (3)
C3—C4—C5	121.5 (3)	C11—C12—N3	119.2 (3)
C3—C4—H4	119.2	C13—C12—N3	119.1 (3)
C5—C4—H4	119.2	C12—C13—C14	119.6 (3)
C4—C5—C6	119.0 (3)	C12—C13—H13	120.2
C4—C5—H5	120.5	C14—C13—H13	120.2
C6—C5—H5	120.5	C13—C14—C15	119.6 (3)
C5—C6—C1	121.3 (3)	C13—C14—H14	120.2
C5—C6—H6	119.3	C15—C14—H14	120.2
C1—C6—H6	119.3	C10—C15—C14	119.9 (3)
O1—C7—H7A	109.5	C10—C15—H15	120.1
O1—C7—H7B	109.5	C14—C15—H15	120.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.03	2.856 (3)	162
C8—H8···O2ⁱ	0.93	2.47	3.231 (3)	139

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₄
M_r	299.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.9886 (13), 29.543 (3), 7.4163 (14)
β (°)	109.229 (2)
V (Å³)	1445.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.17 × 0.13

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.980, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	11773, 3140, 1547
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.160, 1.02
No. of reflections	3140
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.20

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—H2···O2ⁱ	0.86	2.03	2.856 (3)	162
C8—H8···O2ⁱ	0.93	2.47	3.231 (3)	139

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

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

References

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