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

In the title compound, C(15)H(13)N(3)O(4), the mol-ecule exists in a trans configuration with respect to the methyl-idene unit. The dihedral angle between the two benzene rings is 6.8 (2)°. The C-N-NH-C torsion angle is 3.4 (3)°. The mol-ecule possesses an intra-molecular N-H⋯O hydrogen bond. In the crystal structure, adjacent mol-ecules are linked through inter-molecular C-H⋯O hydrogen bonds, forming dimers.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban & Li (2008a ▶,b ▶); Li & Ban (2009a ▶,b ▶); Yehye et al. (2008 ▶); Fun, Patil, Jebas et al. (2008 ▶); Fun, Patil, Rao et al. (2008 ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C15H13N3O4

M = 299.28

Monoclinic,

a = 11.1843 (2) Å

b = 11.3718 (3) Å

c = 13.0519 (2) Å

β = 121.792 (2)°

V = 1410.96 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.15 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.985, T max = 0.988

8270 measured reflections

3048 independent reflections

1964 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.138

S = 1.02

3048 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablocks global, I. DOI: 10.1107/S160053680905079X/wn2369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905079X/wn2369Isup2.hkl

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

C15H13N3O4	F(000) = 624
Mr = 299.28	Dx = 1.409 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2137 reflections
a = 11.1843 (2) Å	θ = 2.6–27.7°
b = 11.3718 (3) Å	µ = 0.11 mm−1
c = 13.0519 (2) Å	T = 298 K
β = 121.792 (2)°	Block, colorless
V = 1410.96 (6) Å3	0.15 × 0.13 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3048 independent reflections
Radiation source: fine-focus sealed tube	1964 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.985, Tmax = 0.988	k = −14→9
8270 measured reflections	l = −16→15

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0691P)2 + 0.1341P] where P = (Fo2 + 2Fc2)/3
3048 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.02468 (14)	0.74628 (13)	0.11097 (11)	0.0533 (4)
N2	0.10276 (15)	0.75892 (13)	0.23349 (11)	0.0542 (4)
N3	−0.37828 (15)	0.80034 (14)	−0.46112 (12)	0.0584 (4)
O1	0.18128 (13)	0.87506 (11)	0.43486 (10)	0.0632 (4)
O2	0.16350 (19)	0.56837 (12)	0.25823 (12)	0.0989 (6)
O3	−0.36814 (16)	0.71210 (14)	−0.50895 (11)	0.0841 (5)
O4	−0.45977 (16)	0.87945 (13)	−0.51687 (11)	0.0874 (5)
C1	−0.12755 (16)	0.82699 (14)	−0.08248 (13)	0.0477 (4)
C2	−0.13227 (17)	0.72335 (14)	−0.14102 (14)	0.0513 (4)
H2	−0.0804	0.6587	−0.0958	0.062*
C3	−0.21222 (17)	0.71486 (15)	−0.26456 (14)	0.0518 (4)
H3	−0.2148	0.6454	−0.3032	0.062*
C4	−0.28832 (16)	0.81139 (14)	−0.32966 (13)	0.0477 (4)
C5	−0.28638 (18)	0.91571 (15)	−0.27587 (15)	0.0572 (4)
H5	−0.3389	0.9798	−0.3219	0.069*
C6	−0.20458 (18)	0.92326 (15)	−0.15175 (15)	0.0559 (4)
H6	−0.2009	0.9936	−0.1139	0.067*
C7	−0.04485 (17)	0.83471 (15)	0.04892 (14)	0.0523 (4)
H7	−0.0432	0.9044	0.0870	0.063*
C8	0.17233 (18)	0.66437 (16)	0.30264 (14)	0.0571 (4)
C9	0.26280 (16)	0.68339 (15)	0.43602 (13)	0.0507 (4)
C10	0.26528 (17)	0.78298 (15)	0.49941 (13)	0.0514 (4)
C11	0.35310 (19)	0.78490 (18)	0.62478 (15)	0.0643 (5)
H11	0.3528	0.8500	0.6678	0.077*
C12	0.4398 (2)	0.6917 (2)	0.68511 (16)	0.0730 (6)
H12	0.4982	0.6944	0.7686	0.088*
C13	0.4412 (2)	0.5949 (2)	0.62399 (16)	0.0720 (6)
H13	0.5015	0.5326	0.6653	0.086*
C14	0.35239 (19)	0.59045 (17)	0.50043 (15)	0.0621 (5)
H14	0.3523	0.5238	0.4591	0.075*
C15	0.1754 (2)	0.97515 (17)	0.49824 (18)	0.0720 (6)
H15A	0.1474	0.9507	0.5530	0.108*
H15B	0.1083	1.0306	0.4417	0.108*
H15C	0.2665	1.0114	0.5426	0.108*
H2A	0.102 (2)	0.8277 (12)	0.2684 (17)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0562 (8)	0.0618 (9)	0.0314 (7)	0.0037 (7)	0.0159 (6)	−0.0002 (6)
N2	0.0613 (9)	0.0581 (9)	0.0295 (7)	0.0065 (7)	0.0145 (6)	−0.0012 (6)
N3	0.0601 (9)	0.0703 (10)	0.0373 (7)	0.0068 (8)	0.0204 (7)	0.0109 (7)
O1	0.0706 (8)	0.0654 (8)	0.0440 (6)	0.0069 (6)	0.0237 (6)	−0.0082 (6)
O2	0.1488 (15)	0.0625 (9)	0.0423 (7)	0.0271 (9)	0.0207 (8)	−0.0018 (6)
O3	0.1009 (11)	0.0921 (11)	0.0426 (7)	0.0188 (8)	0.0264 (7)	−0.0010 (7)
O4	0.0927 (11)	0.0905 (10)	0.0455 (7)	0.0317 (8)	0.0135 (7)	0.0184 (7)
C1	0.0465 (9)	0.0548 (10)	0.0384 (8)	0.0013 (7)	0.0200 (7)	0.0037 (7)
C2	0.0539 (9)	0.0515 (10)	0.0405 (8)	0.0102 (7)	0.0195 (7)	0.0098 (7)
C3	0.0561 (10)	0.0537 (10)	0.0395 (8)	0.0074 (7)	0.0209 (7)	0.0023 (7)
C4	0.0454 (8)	0.0590 (10)	0.0342 (8)	0.0042 (7)	0.0178 (7)	0.0091 (7)
C5	0.0594 (10)	0.0542 (10)	0.0471 (9)	0.0126 (8)	0.0204 (8)	0.0150 (8)
C6	0.0601 (10)	0.0521 (10)	0.0456 (9)	0.0072 (8)	0.0210 (8)	0.0021 (7)
C7	0.0546 (10)	0.0542 (10)	0.0400 (8)	0.0029 (8)	0.0194 (7)	−0.0003 (7)
C8	0.0660 (11)	0.0585 (11)	0.0359 (8)	0.0066 (8)	0.0193 (8)	0.0009 (8)
C9	0.0494 (9)	0.0630 (11)	0.0341 (8)	−0.0003 (8)	0.0183 (7)	0.0033 (7)
C10	0.0471 (9)	0.0657 (11)	0.0367 (8)	−0.0049 (8)	0.0189 (7)	−0.0020 (7)
C11	0.0622 (11)	0.0859 (14)	0.0389 (9)	−0.0129 (10)	0.0225 (8)	−0.0119 (9)
C12	0.0604 (11)	0.1071 (17)	0.0325 (9)	−0.0109 (11)	0.0115 (8)	0.0056 (10)
C13	0.0623 (12)	0.0882 (15)	0.0474 (10)	0.0045 (10)	0.0165 (9)	0.0172 (10)
C14	0.0630 (11)	0.0681 (12)	0.0453 (9)	0.0049 (9)	0.0217 (8)	0.0073 (8)
C15	0.0915 (14)	0.0618 (12)	0.0640 (12)	−0.0047 (10)	0.0418 (11)	−0.0136 (9)

N1—C7	1.268 (2)	C5—C6	1.381 (2)
N1—N2	1.3672 (17)	C5—H5	0.9300
N2—C8	1.355 (2)	C6—H6	0.9300
N2—H2A	0.908 (9)	C7—H7	0.9300
N3—O4	1.2127 (18)	C8—C9	1.498 (2)
N3—O3	1.2183 (18)	C9—C14	1.393 (2)
N3—C4	1.467 (2)	C9—C10	1.394 (2)
O1—C10	1.3619 (19)	C10—C11	1.396 (2)
O1—C15	1.429 (2)	C11—C12	1.371 (3)
O2—C8	1.215 (2)	C11—H11	0.9300
C1—C2	1.390 (2)	C12—C13	1.364 (3)
C1—C6	1.392 (2)	C12—H12	0.9300
C1—C7	1.460 (2)	C13—C14	1.379 (2)
C2—C3	1.375 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.375 (2)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.373 (2)	C15—H15C	0.9600
C7—N1—N2	117.55 (14)	C1—C7—H7	120.1
C8—N2—N1	118.97 (14)	O2—C8—N2	121.41 (15)
C8—N2—H2A	120.2 (13)	O2—C8—C9	121.28 (15)
N1—N2—H2A	120.6 (13)	N2—C8—C9	117.30 (15)
O4—N3—O3	123.15 (15)	C14—C9—C10	118.37 (14)
O4—N3—C4	118.28 (15)	C14—C9—C8	114.99 (15)
O3—N3—C4	118.56 (14)	C10—C9—C8	126.64 (15)
C10—O1—C15	118.79 (13)	O1—C10—C9	117.77 (13)
C2—C1—C6	118.59 (14)	O1—C10—C11	122.89 (16)
C2—C1—C7	120.89 (14)	C9—C10—C11	119.34 (16)
C6—C1—C7	120.52 (15)	C12—C11—C10	120.60 (18)
C3—C2—C1	121.13 (14)	C12—C11—H11	119.7
C3—C2—H2	119.4	C10—C11—H11	119.7
C1—C2—H2	119.4	C13—C12—C11	120.70 (16)
C4—C3—C2	118.51 (15)	C13—C12—H12	119.7
C4—C3—H3	120.7	C11—C12—H12	119.7
C2—C3—H3	120.7	C12—C13—C14	119.37 (18)
C5—C4—C3	122.42 (14)	C12—C13—H13	120.3
C5—C4—N3	119.23 (14)	C14—C13—H13	120.3
C3—C4—N3	118.31 (15)	C13—C14—C9	121.58 (18)
C4—C5—C6	118.42 (15)	C13—C14—H14	119.2
C4—C5—H5	120.8	C9—C14—H14	119.2
C6—C5—H5	120.8	O1—C15—H15A	109.5
C5—C6—C1	120.92 (16)	O1—C15—H15B	109.5
C5—C6—H6	119.5	H15A—C15—H15B	109.5
C1—C6—H6	119.5	O1—C15—H15C	109.5
N1—C7—C1	119.88 (16)	H15A—C15—H15C	109.5
N1—C7—H7	120.1	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.91 (1)	1.94 (2)	2.644 (2)	133 (2)
C3—H3···O2i	0.93	2.50	3.260 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.91 (1)	1.94 (2)	2.644 (2)	133 (2)
C3—H3⋯O2i	0.93	2.50	3.260 (2)	140

Symmetry code: (i) .