(E)-4-Methyl-N′-(3-nitro­benzyl­idene)benzohydrazide

Abstract

In the title compound, C₁₅H₁₃N₃O₃, 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, mol­ecules 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 _r = 283.28

• Orthorhombic,

• a = 32.657 (3) Å

• b = 4.7861 (15) Å

• c = 8.7596 (12) Å

• V = 1369.1 (5) ų

• 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

• Δρ_max = 0.13 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

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

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) .

supplementary crystallographic information

Comment

As a continuation of our work on similar compounds (Liu & You, 2010; Liu & Wang, 2010), we report herein the crystal structure of the title compound a new hydrazone.

The molecular structure of the title compound is shown in Fig. 1. The two benzene ring system are inclined at a dihedral angle of 0.6 (3)°. All the bond lengths are comparable to those observed in related structures (Xu et al., 2009; Shafiq et al., 2009) and those we reported previously.

In the crystal structure, molecules are linked through N–H···O hydrogen bonds, to form one-dimensional chains running along the b axis (Fig. 2 and Table 1).

Experimental

The title compound was prepared by the condensation reaction of 3-nitrobenzaldehyde (0.05 mol, 7.6 g) and 4-methylbenzohydrazide (0.05 mol, 7.5 g) in anhydrous methanol (100 ml) at ambient temperature. Yellow block-shaped single crystals were obtained by slow evaporation of the solution for several days.

Refinement

Anomalous dispersion was negligible and the absolute structure could not be determined in the present experiment. H3 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. The remaining H atoms were positioned geometrically and constrained to ride on their parent atoms, with C–H distances of 0.93–0.96 Å, and with U_iso(H) = 1.2U_eq(C) and 1.5U_eq(C15).

Figures

Fig. 1.

The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Fig. 2.

The molecular packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

Crystal data

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

Data collection

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

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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, º)

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

Hydrogen-bond geometry (Å, º)

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) x, y−1, z.