N′-(2-Chloro­benzyl­idene)-4-nitro­benzohydrazide

Tang, C.-B.

doi:10.1107/S1600536811055589

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o335

doi:10.1107/S1600536811055589

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N′-(2-Chlorobenzylidene)-4-nitrobenzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@yahoo.cn

(Received 24 December 2011; accepted 25 December 2011; online 11 January 2012)

In the title compound, C₁₄H₁₀ClN₃O₃, the dihedral angle between the benzene rings is 6.64 (13)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains running along the c axis direction.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ); Pyta et al. (2010 ); Angelusiu et al. (2010 ). For related structures, see: Fun et al. (2008 ); Singh & Singh (2010 ); Ahmad et al. (2010 ); Tang (2010 , 2011 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₀ClN₃O₃
M_r = 303.70
Monoclinic, P 2₁ /c
a = 11.2332 (18) Å
b = 13.3778 (18) Å
c = 8.9770 (16) Å
β = 90.408 (2)°
V = 1349.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.949, T_max = 0.957
10640 measured reflections
2931 independent reflections
1882 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.146
S = 1.03
2931 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.89 (1)	2.06 (1)	2.915 (3)	160 (3)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055589/su2353sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055589/su2353Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055589/su2353Isup3.cml

checkCIF report

Comment top

Hydrazone compounds have received much attention in biological and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work on the structural study on such compounds (Tang, 2010, 2011), we reports herein on the crystal structure of the title new hydrazone compound.

In the molecule of the title compound (Fig. 1), the dihedral angle between the two benzene rings is 6.64 (13)°. Bond lengths in the compound are normal (Allen et al., 1987) and comparable to those in the similar compounds (Tang, 2010; Tang, 2011).

In the crystal, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains running along the c axis direction (Fig. 2).

Related literature top

For general background to hydrazones, see: Rasras et al. (2010); Pyta et al. (2010); Angelusiu et al. (2010). For related structures, see: Fun et al. (2008); Singh & Singh (2010); Ahmad et al. (2010); Tang (2010, 2011). For reference bond-length data, see: Allen et al. (1987).

Experimental top

2-Chlorobenzaldehyde (0.1 mmol, 14.1 mg) and 4-nitrobenzohydrazide (0.1 mmol, 18.2 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear yellow solution. Yellow needle-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound, viewed along the b axis, with hydrogen bonds shown as dashed lines.

N'-(2-Chlorobenzylidene)-4-nitrobenzohydrazide top

Crystal data top

C₁₄H₁₀ClN₃O₃	F(000) = 624
M_r = 303.70	D_x = 1.495 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2332 (18) Å	Cell parameters from 2464 reflections
b = 13.3778 (18) Å	θ = 2.4–24.5°
c = 8.9770 (16) Å	µ = 0.30 mm⁻¹
β = 90.408 (2)°	T = 298 K
V = 1349.0 (4) Å³	Cut from needle, yellow
Z = 4	0.18 × 0.17 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2931 independent reflections
Radiation source: fine-focus sealed tube	1882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.949, T_max = 0.957	k = −14→17
10640 measured reflections	l = −11→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0569P)² + 0.5874P] where P = (F_o² + 2F_c²)/3
2931 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.36 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₄H₁₀ClN₃O₃	V = 1349.0 (4) Å³
M_r = 303.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2332 (18) Å	µ = 0.30 mm⁻¹
b = 13.3778 (18) Å	T = 298 K
c = 8.9770 (16) Å	0.18 × 0.17 × 0.15 mm
β = 90.408 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2931 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1882 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.957	R_int = 0.045
10640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.36 e Å⁻³
2931 reflections	Δρ_min = −0.29 e Å⁻³
193 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
Cl1	0.23505 (8)	0.62569 (6)	1.10065 (9)	0.0782 (3)
H2	0.246 (3)	0.265 (2)	1.1045 (13)	0.080*
N1	0.18950 (18)	0.33163 (14)	0.9198 (2)	0.0444 (5)
N2	0.23517 (19)	0.25548 (14)	1.0072 (2)	0.0446 (5)
N3	0.4488 (2)	−0.1478 (2)	1.3026 (3)	0.0667 (7)
O1	0.26845 (19)	0.15983 (13)	0.80373 (18)	0.0620 (5)
O2	0.4173 (3)	−0.23176 (19)	1.2688 (3)	0.1126 (10)
O3	0.5111 (2)	−0.12928 (18)	1.4092 (3)	0.0902 (8)
C1	0.1488 (2)	0.59971 (19)	0.9450 (3)	0.0513 (6)
C2	0.1308 (2)	0.50090 (18)	0.8991 (3)	0.0452 (6)
C3	0.0625 (2)	0.4872 (2)	0.7698 (3)	0.0553 (7)
H3	0.0493	0.4227	0.7348	0.066*
C4	0.0149 (3)	0.5657 (3)	0.6941 (3)	0.0679 (8)
H4	−0.0312	0.5541	0.6094	0.082*
C5	0.0344 (3)	0.6622 (2)	0.7416 (4)	0.0709 (9)
H5	0.0020	0.7154	0.6885	0.085*
C6	0.1015 (3)	0.6800 (2)	0.8673 (4)	0.0644 (8)
H6	0.1149	0.7450	0.8998	0.077*
C7	0.1807 (2)	0.41629 (18)	0.9816 (3)	0.0463 (6)
H7	0.2061	0.4247	1.0796	0.056*
C8	0.2731 (2)	0.17126 (17)	0.9389 (3)	0.0434 (6)
C9	0.3213 (2)	0.09038 (17)	1.0373 (2)	0.0392 (5)
C10	0.3769 (2)	0.10957 (18)	1.1718 (3)	0.0443 (6)
H10	0.3845	0.1751	1.2052	0.053*
C11	0.4216 (2)	0.03155 (19)	1.2576 (3)	0.0495 (6)
H11	0.4605	0.0441	1.3474	0.059*
C12	0.4069 (2)	−0.06443 (19)	1.2070 (3)	0.0479 (6)
C13	0.3536 (2)	−0.08568 (19)	1.0728 (3)	0.0558 (7)
H13	0.3456	−0.1514	1.0404	0.067*
C14	0.3122 (2)	−0.00768 (19)	0.9871 (3)	0.0539 (7)
H14	0.2777	−0.0207	0.8947	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1009 (6)	0.0532 (5)	0.0802 (6)	−0.0085 (4)	−0.0221 (5)	−0.0047 (4)
N1	0.0560 (12)	0.0374 (11)	0.0397 (11)	−0.0027 (9)	−0.0030 (9)	0.0046 (9)
N2	0.0662 (13)	0.0345 (11)	0.0329 (11)	−0.0010 (9)	−0.0045 (9)	−0.0007 (9)
N3	0.0637 (15)	0.0569 (16)	0.0792 (18)	0.0213 (12)	−0.0113 (13)	0.0006 (14)
O1	0.1089 (16)	0.0463 (10)	0.0308 (10)	−0.0018 (10)	−0.0020 (9)	−0.0018 (8)
O2	0.134 (2)	0.0514 (15)	0.152 (3)	0.0189 (14)	−0.0636 (19)	0.0076 (15)
O3	0.1053 (18)	0.0902 (18)	0.0747 (16)	0.0349 (14)	−0.0268 (14)	−0.0009 (13)
C1	0.0545 (14)	0.0475 (15)	0.0518 (15)	−0.0003 (12)	0.0045 (12)	0.0070 (12)
C2	0.0504 (13)	0.0428 (14)	0.0425 (14)	0.0001 (11)	0.0078 (11)	0.0052 (11)
C3	0.0590 (16)	0.0573 (17)	0.0496 (16)	0.0051 (13)	−0.0006 (12)	−0.0021 (13)
C4	0.0709 (19)	0.078 (2)	0.0548 (17)	0.0151 (16)	−0.0082 (14)	0.0057 (16)
C5	0.081 (2)	0.063 (2)	0.068 (2)	0.0191 (16)	0.0024 (17)	0.0202 (16)
C6	0.0742 (19)	0.0443 (16)	0.075 (2)	0.0044 (14)	0.0094 (16)	0.0094 (14)
C7	0.0579 (14)	0.0440 (14)	0.0369 (13)	−0.0017 (11)	−0.0019 (11)	0.0026 (11)
C8	0.0579 (14)	0.0369 (13)	0.0353 (13)	−0.0113 (11)	−0.0005 (10)	0.0003 (10)
C9	0.0476 (12)	0.0365 (12)	0.0337 (12)	−0.0051 (10)	0.0043 (10)	−0.0016 (10)
C10	0.0510 (13)	0.0369 (13)	0.0450 (14)	−0.0038 (10)	−0.0014 (11)	−0.0087 (11)
C11	0.0507 (14)	0.0530 (16)	0.0446 (14)	0.0034 (12)	−0.0080 (11)	−0.0057 (12)
C12	0.0468 (13)	0.0443 (14)	0.0526 (15)	0.0089 (11)	0.0004 (11)	0.0007 (12)
C13	0.0694 (17)	0.0355 (13)	0.0625 (18)	0.0044 (12)	−0.0095 (14)	−0.0119 (12)
C14	0.0749 (18)	0.0416 (14)	0.0450 (14)	−0.0001 (13)	−0.0130 (13)	−0.0117 (12)

Geometric parameters (Å, º) top

Cl1—C1	1.729 (3)	C4—H4	0.9300
N1—C7	1.265 (3)	C5—C6	1.373 (4)
N1—N2	1.382 (3)	C5—H5	0.9300
N2—C8	1.353 (3)	C6—H6	0.9300
N2—H2	0.891 (10)	C7—H7	0.9300
N3—O3	1.207 (3)	C8—C9	1.495 (3)
N3—O2	1.216 (3)	C9—C10	1.380 (3)
N3—C12	1.482 (3)	C9—C14	1.390 (3)
O1—C8	1.224 (3)	C10—C11	1.389 (3)
C1—C6	1.385 (4)	C10—H10	0.9300
C1—C2	1.399 (3)	C11—C12	1.372 (3)
C2—C3	1.399 (3)	C11—H11	0.9300
C2—C7	1.462 (3)	C12—C13	1.371 (3)
C3—C4	1.358 (4)	C13—C14	1.375 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.377 (5)	C14—H14	0.9300

C7—N1—N2	116.14 (19)	N1—C7—C2	120.1 (2)
C8—N2—N1	118.26 (19)	N1—C7—H7	119.9
C8—N2—H2	122 (2)	C2—C7—H7	119.9
N1—N2—H2	120 (2)	O1—C8—N2	122.8 (2)
O3—N3—O2	123.6 (3)	O1—C8—C9	120.5 (2)
O3—N3—C12	119.0 (3)	N2—C8—C9	116.7 (2)
O2—N3—C12	117.4 (3)	C10—C9—C14	119.4 (2)
C6—C1—C2	122.0 (3)	C10—C9—C8	122.8 (2)
C6—C1—Cl1	117.5 (2)	C14—C9—C8	117.8 (2)
C2—C1—Cl1	120.5 (2)	C9—C10—C11	120.3 (2)
C1—C2—C3	116.5 (2)	C9—C10—H10	119.8
C1—C2—C7	121.9 (2)	C11—C10—H10	119.8
C3—C2—C7	121.6 (2)	C12—C11—C10	118.5 (2)
C4—C3—C2	121.7 (3)	C12—C11—H11	120.7
C4—C3—H3	119.2	C10—C11—H11	120.7
C2—C3—H3	119.2	C13—C12—C11	122.4 (2)
C3—C4—C5	120.6 (3)	C13—C12—N3	119.2 (2)
C3—C4—H4	119.7	C11—C12—N3	118.4 (2)
C5—C4—H4	119.7	C12—C13—C14	118.5 (2)
C6—C5—C4	120.1 (3)	C12—C13—H13	120.7
C6—C5—H5	119.9	C14—C13—H13	120.7
C4—C5—H5	119.9	C13—C14—C9	120.7 (2)
C5—C6—C1	119.1 (3)	C13—C14—H14	119.6
C5—C6—H6	120.4	C9—C14—H14	119.6
C1—C6—H6	120.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.89 (1)	2.06 (1)	2.915 (3)	160 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀ClN₃O₃
M_r	303.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.2332 (18), 13.3778 (18), 8.9770 (16)
β (°)	90.408 (2)
V (Å³)	1349.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.18 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	10640, 2931, 1882
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.146, 1.03
No. of reflections	2931
No. of parameters	193
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.29

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.89 (1)	2.064 (14)	2.915 (3)	160 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976. Web of Science CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055–2062. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2002). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Sujith, K. V., Patil, P. S., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1961–o1962. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pyta, K., Przybylski, P., Huczynski, A., Hoser, A., Wozniak, K., Schilf, W., Kamienski, B., Grech, E. & Brzezinski, B. (2010). J. Mol. Struct. 970, 147–154. Web of Science CSD CrossRef CAS Google Scholar
Rasras, A. J. M., Al-Tel, T. H., Al-Aboudi, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307–2313. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tang, C.-B. (2010). Acta Cryst. E66, o2482. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tang, C.-B. (2011). Acta Cryst. E67, o271. Web of Science CSD CrossRef IUCr Journals Google Scholar