N'-(2-Meth-oxy-benzyl-idene)-4-nitro-benzohydrazide.

The mol-ecule of the title compound, C(15)H(13)N(3)O(4), 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, mol-ecules are linked through inter-molecular 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 = 299.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.154

S = 0.99

3129 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 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: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

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

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

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

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

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

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(Fo2) + (0.0427P)2] where P = (Fo2 + 2Fc2)/3
3129 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.16 e Å−3
1 restraint	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	0.30611 (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*

	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)

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

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)

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) .