(E)-N'-(2-Meth-oxy-benzyl-idene)-3-nitro-benzohydrazide.

In the title compound, C(15)H(13)N(3)O(4), the two substituted benzene rings form a dihedral angle of 10.9 (3)°. In the crystal, inter-molecular C-H⋯O and N-H⋯O hydrogen bonds link mol-ecules 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 = 299.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.160

S = 1.02

3140 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025542/rz2618sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811025542/rz2618Isup3.cml

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

C15H13N3O4	F(000) = 624
Mr = 299.28	Dx = 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

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

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(Fo2) + (0.0565P)2 + 0.2817P] where P = (Fo2 + 2Fc2)/3
3140 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .