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

Hu, H.-N.; Liu, S.-Y.

doi:10.1107/S1600536812019198

organic compounds

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Volume 68| Part 6| June 2012| Page o1613

doi:10.1107/S1600536812019198

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

Hua-Nan Hu ^a and Shi-Yong Liu ^a ^*

^aCollege of Chemistry & Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China
^*Correspondence e-mail: liushiyong2012@yahoo.cn

(Received 28 April 2012; accepted 29 April 2012; online 5 May 2012)

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, P c a 2₁
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[F² > 2σ(F²)] = 0.049
wR(F²) = 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

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) x, y-1, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019198/hb6769sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812019198/hb6769Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	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.

(E)-4-Methyl-N'-(3-nitrobenzylidene)benzohydrazide top

Crystal data top

C₁₅H₁₃N₃O₃	D_x = 1.374 Mg m⁻³
M_r = 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 top

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

Refinement top

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(F_o²) + (0.0473P)² + 0.1113P] where P = (F_o² + 2F_c²)/3
2539 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.13 e Å⁻³
2 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₃	V = 1369.1 (5) Å³
M_r = 283.28	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 32.657 (3) Å	µ = 0.10 mm⁻¹
b = 4.7861 (15) Å	T = 298 K
c = 8.7596 (12) Å	0.20 × 0.20 × 0.17 mm

Data collection top

Bruker SMART CCD diffractometer	2539 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2036 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.045
9086 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	2 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.13 e Å⁻³
2539 reflections	Δρ_min = −0.17 e Å⁻³
195 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₃O₃
M_r	283.28
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	32.657 (3), 4.7861 (15), 8.7596 (12)
V (Å³)	1369.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9086, 2539, 2036
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.103, 1.04
No. of reflections	2539
No. of parameters	195
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.17

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3ⁱ	0.891 (10)	2.128 (18)	2.909 (3)	146 (2)

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors acknowledge the Zhejiang Provincial Natural Science Foundation of China (project No. Y12B020017).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, S.-Y. & Wang, X. (2010). Acta Cryst. E66, o1775. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & You, Z. (2010). Acta Cryst. E66, o1652. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2898. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, L., Huang, S.-S., Zhang, B.-J., Wang, S.-Y. & Zhang, H.-L. (2009). Acta Cryst. E65, o2412. Web of Science CSD CrossRef IUCr Journals Google Scholar