(E)-4-Methyl-N'-(3-nitro-benzyl-idene)benzohydrazide.

In the title compound, C(15)H(13)N(3)O(3), the dihedral angle between the benzene rings is 1.01 (3)° and that between the nitro group and its attached ring is 5.99 (15)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds generating C(4) chains along [010].

Related literature

For related structures, see: Liu & You (2010 ▶); Liu & Wang (2010 ▶); Xu et al. (2009 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C15H13N3O3

M = 283.28

Orthorhombic,

a = 32.657 (3) Å

b = 4.7861 (15) Å

c = 8.7596 (12) Å

V = 1369.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.981, T max = 0.984

9086 measured reflections

2539 independent reflections

2036 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.103

S = 1.04

2539 reflections

195 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.17 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 datablock(s) global, I. DOI: 10.1107/S1600536812019198/hb6769sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019198/hb6769Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019198/hb6769Isup3.cml

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

C15H13N3O3	Dx = 1.374 Mg m−3
Mr = 283.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 1981 reflections
a = 32.657 (3) Å	θ = 2.5–24.3°
b = 4.7861 (15) Å	µ = 0.10 mm−1
c = 8.7596 (12) Å	T = 298 K
V = 1369.1 (5) Å3	Block, yellow
Z = 4	0.20 × 0.20 × 0.17 mm
F(000) = 592

Bruker SMART CCD diffractometer	2539 independent reflections
Radiation source: fine-focus sealed tube	2036 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −39→37
Tmin = 0.981, Tmax = 0.984	k = −5→5
9086 measured reflections	l = −10→10

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.1113P] where P = (Fo2 + 2Fc2)/3
2539 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.13 e Å−3
2 restraints	Δρmin = −0.17 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	0.85121 (8)	0.5734 (5)	0.4452 (2)	0.0467 (6)
N2	0.70734 (7)	0.2646 (4)	0.2869 (3)	0.0444 (5)
N3	0.66666 (7)	0.2015 (4)	0.2812 (3)	0.0455 (5)
O1	0.88853 (7)	0.5929 (5)	0.4514 (3)	0.0749 (7)
O2	0.82822 (7)	0.7214 (4)	0.5169 (2)	0.0597 (6)
O3	0.64841 (6)	0.6273 (4)	0.3664 (2)	0.0553 (5)
C1	0.77578 (8)	0.1201 (5)	0.2510 (3)	0.0413 (6)
C2	0.79253 (8)	0.3213 (5)	0.3444 (3)	0.0377 (6)
H2	0.7758	0.4289	0.4072	0.045*
C3	0.83377 (8)	0.3605 (5)	0.3438 (3)	0.0382 (6)
C4	0.85976 (8)	0.2118 (6)	0.2508 (3)	0.0488 (7)
H4	0.8878	0.2448	0.2521	0.059*
C5	0.84325 (9)	0.0139 (6)	0.1563 (3)	0.0527 (7)
H5	0.8601	−0.0881	0.0914	0.063*
C6	0.80177 (8)	−0.0341 (5)	0.1572 (3)	0.0457 (7)
H6	0.7909	−0.1717	0.0942	0.055*
C7	0.73153 (8)	0.0702 (6)	0.2463 (3)	0.0479 (7)
H7	0.7213	−0.1012	0.2140	0.057*
C8	0.63869 (8)	0.3942 (5)	0.3216 (3)	0.0418 (6)
C9	0.59528 (8)	0.3070 (5)	0.3091 (3)	0.0405 (6)
C10	0.56597 (9)	0.4440 (6)	0.3943 (4)	0.0591 (8)
H10	0.5739	0.5841	0.4617	0.071*
C11	0.52522 (10)	0.3763 (7)	0.3809 (4)	0.0677 (9)
H11	0.5062	0.4680	0.4418	0.081*
C12	0.51204 (9)	0.1772 (7)	0.2801 (4)	0.0600 (8)
C13	0.54139 (9)	0.0401 (7)	0.1948 (3)	0.0622 (9)
H13	0.5333	−0.0988	0.1269	0.075*
C14	0.58242 (9)	0.1047 (6)	0.2083 (3)	0.0533 (8)
H14	0.6015	0.0107	0.1488	0.064*
C15	0.46734 (9)	0.0998 (9)	0.2613 (5)	0.0889 (12)
H15A	0.4505	0.2489	0.2990	0.133*
H15B	0.4617	−0.0678	0.3177	0.133*
H15C	0.4615	0.0692	0.1551	0.133*
H3	0.6588 (7)	0.025 (3)	0.266 (3)	0.050 (8)*

	U11	U22	U33	U12	U13	U23
N1	0.0515 (16)	0.0457 (13)	0.0428 (13)	−0.0090 (12)	−0.0092 (12)	0.0008 (11)
N2	0.0438 (14)	0.0381 (12)	0.0512 (12)	−0.0091 (10)	−0.0044 (11)	−0.0003 (11)
N3	0.0398 (13)	0.0312 (12)	0.0655 (15)	−0.0094 (10)	0.0000 (11)	−0.0075 (12)
O1	0.0505 (14)	0.0829 (16)	0.0915 (17)	−0.0158 (12)	−0.0164 (12)	−0.0160 (13)
O2	0.0715 (14)	0.0567 (13)	0.0507 (12)	−0.0013 (12)	0.0013 (10)	−0.0194 (11)
O3	0.0679 (13)	0.0328 (10)	0.0651 (12)	−0.0097 (9)	0.0031 (11)	−0.0116 (9)
C1	0.0447 (16)	0.0338 (14)	0.0456 (15)	0.0006 (12)	−0.0042 (13)	0.0025 (12)
C2	0.0428 (16)	0.0323 (12)	0.0379 (14)	0.0017 (11)	0.0006 (11)	−0.0043 (11)
C3	0.0446 (15)	0.0355 (13)	0.0343 (14)	−0.0024 (12)	−0.0025 (12)	−0.0003 (11)
C4	0.0428 (16)	0.0509 (17)	0.0526 (17)	0.0012 (13)	−0.0004 (14)	0.0031 (15)
C5	0.0582 (19)	0.0543 (18)	0.0456 (15)	0.0114 (14)	0.0079 (15)	−0.0043 (15)
C6	0.0583 (18)	0.0373 (15)	0.0415 (14)	0.0008 (13)	−0.0084 (14)	−0.0067 (13)
C7	0.0512 (18)	0.0368 (15)	0.0555 (17)	−0.0060 (13)	−0.0034 (14)	−0.0054 (13)
C8	0.0505 (16)	0.0337 (14)	0.0412 (15)	−0.0047 (12)	0.0005 (12)	−0.0008 (12)
C9	0.0473 (16)	0.0310 (13)	0.0433 (15)	0.0013 (11)	0.0024 (12)	0.0023 (11)
C10	0.062 (2)	0.0535 (17)	0.0621 (19)	−0.0044 (15)	0.0135 (16)	−0.0127 (16)
C11	0.059 (2)	0.065 (2)	0.078 (2)	0.0081 (17)	0.0222 (18)	−0.007 (2)
C12	0.0511 (19)	0.068 (2)	0.0614 (19)	0.0021 (15)	0.0041 (16)	0.0096 (18)
C13	0.055 (2)	0.071 (2)	0.0607 (19)	−0.0138 (16)	−0.0062 (15)	−0.0175 (16)
C14	0.0497 (19)	0.0525 (18)	0.0577 (18)	−0.0012 (14)	0.0035 (13)	−0.0163 (14)
C15	0.048 (2)	0.127 (3)	0.091 (3)	−0.002 (2)	0.000 (2)	0.008 (3)

N1—O2	1.208 (3)	C6—H6	0.9300
N1—O1	1.224 (3)	C7—H7	0.9300
N1—C3	1.467 (3)	C8—C9	1.482 (3)
N2—C7	1.272 (3)	C9—C14	1.376 (3)
N2—N3	1.364 (3)	C9—C10	1.379 (4)
N3—C8	1.345 (3)	C10—C11	1.375 (4)
N3—H3	0.891 (10)	C10—H10	0.9300
O3—C8	1.225 (3)	C11—C12	1.369 (5)
C1—C2	1.377 (3)	C11—H11	0.9300
C1—C6	1.393 (4)	C12—C13	1.381 (4)
C1—C7	1.465 (3)	C12—C15	1.515 (4)
C2—C3	1.360 (3)	C13—C14	1.380 (4)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.375 (4)	C14—H14	0.9300
C4—C5	1.369 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.374 (4)	C15—H15C	0.9600
C5—H5	0.9300
O2—N1—O1	123.4 (2)	O3—C8—N3	122.2 (2)
O2—N1—C3	118.7 (2)	O3—C8—C9	121.9 (2)
O1—N1—C3	117.8 (2)	N3—C8—C9	115.9 (2)
C7—N2—N3	115.6 (2)	C14—C9—C10	118.0 (3)
C8—N3—N2	120.0 (2)	C14—C9—C8	122.5 (2)
C8—N3—H3	119.5 (16)	C10—C9—C8	119.4 (2)
N2—N3—H3	119.7 (16)	C11—C10—C9	120.9 (3)
C2—C1—C6	118.6 (2)	C11—C10—H10	119.5
C2—C1—C7	121.5 (2)	C9—C10—H10	119.5
C6—C1—C7	119.9 (2)	C12—C11—C10	121.6 (3)
C3—C2—C1	119.2 (2)	C12—C11—H11	119.2
C3—C2—H2	120.4	C10—C11—H11	119.2
C1—C2—H2	120.4	C11—C12—C13	117.5 (3)
C2—C3—C4	122.8 (2)	C11—C12—C15	122.9 (3)
C2—C3—N1	118.6 (2)	C13—C12—C15	119.6 (3)
C4—C3—N1	118.6 (2)	C14—C13—C12	121.4 (3)
C5—C4—C3	118.3 (3)	C14—C13—H13	119.3
C5—C4—H4	120.9	C12—C13—H13	119.3
C3—C4—H4	120.9	C9—C14—C13	120.6 (3)
C4—C5—C6	120.0 (3)	C9—C14—H14	119.7
C4—C5—H5	120.0	C13—C14—H14	119.7
C6—C5—H5	120.0	C12—C15—H15A	109.5
C5—C6—C1	121.0 (2)	C12—C15—H15B	109.5
C5—C6—H6	119.5	H15A—C15—H15B	109.5
C1—C6—H6	119.5	C12—C15—H15C	109.5
N2—C7—C1	119.0 (2)	H15A—C15—H15C	109.5
N2—C7—H7	120.5	H15B—C15—H15C	109.5
C1—C7—H7	120.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3i	0.89 (1)	2.13 (2)	2.909 (3)	146 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3i	0.89 (1)	2.13 (2)	2.909 (3)	146 (2)

Symmetry code: (i) .