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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Page o2177
doi:10.1107/S1600536808034107

(E)-N′-(2-Chloro-5-nitro­benzyl­­idene)-4-meth­oxy­benzohydrazide

Hong-Yan Bana* and Cong-Ming Lib

aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China, and bCollege of Sciences, Shenyang University, Shenyang 110044, People's Republic of China
*Correspondence e-mail: hongyan_ban@163.com

(Received 9 October 2008; accepted 18 October 2008; online 25 October 2008)

In the title compound, C15H12ClN3O4, the benzohydrazide group is not planar and the mol­ecule exists in a trans configuration with respect to the methyl­idene unit. The dihedral angle between the two substituted benzene rings is 0.4 (3)°. In the crystal structure, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds, forming chains parallel to the c axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007[Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett. 17, 3774-3777.]); Raj et al. (2007[Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425-429.]); Jimenez-Pulido et al. (2008[Jimenez-Pulido, S. B., Linares-Ordonez, F. M., Martinez-Martos, J. M., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Ramirez-Exposito, M. J. (2008). J. Inorg. Biochem. 102, 1677-1683.]). For related structures, see: Yehye et al. (2008[Yehye, W. A., Rahman, N. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1824.]); Fun, Patil, Jebas et al. (2008[Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594-o1595.]); Yang et al. (2008[Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186.]); Ejsmont et al. (2008[Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128.]); Fun, Patil, Rao et al. (2008[Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.]). For reference bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data

  • C15H12ClN3O4

  • Mr = 333.73

  • Monoclinic, C c

  • a = 11.724 (2) Å

  • b = 13.482 (3) Å

  • c = 9.4259 (19) Å

  • β = 97.199 (3)°

  • V = 1478.1 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 298 (2) K

  • 0.20 × 0.20 × 0.17 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.946, Tmax = 0.953

  • 4284 measured reflections

  • 2735 independent reflections

  • 2320 reflections with I > 2σ(I)

  • Rint = 0.015
Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.089

  • S = 1.04

  • 2735 reflections

  • 212 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.19 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1079 Friedel pairs

  • Flack parameter: −0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O1i 0.897 (10) 2.150 (15) 2.994 (3) 156 (3)
Symmetry code: (i) [x, -y+1, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034107/rz2255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034107/rz2255Isup2.hkl

checkCIF report


Comment top

Hydrazones derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of hydrazones have been synthesized and structurally characterized (Yehye et al., 2008; Fun, Patil, Jebas et al., 2008; Yang et al., 2008; Ejsmont et al., 2008). We report herein the crytal structure of the title new hydrazone compound.

In the structure of the title compound (Fig. 1), the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 0.4 (3)°. In the 2-chloro-5-nitrophenyl unit, the nitro group is slightly twisted from the mean plane of the C1–C6 ring with a dihedral angle of 7.4 (3)°. The same pattern can ben observed in a similar hydrazone compound (Fun, Patil, Rao et al., 2008). In the 4-methoxyphenyl unit, the methoxy group is nearly coplanar with the mean plane of the C9–C14 ring, with atom C15 deviating from the C9–C14 ring by 0.098 (2) Å. The C7-N1-N2-C8 torsion angle is 7.3 (3)°. The bond distances and angles are in normal ranges (Allen et al., 1987).

In the crystal structure, molecules are linked by intermolecular N—H···O hydrogen bonds (Table 1), to form chains parallel to the c axis (Fig. 2).

Related literature top

For the biological activities of hydrazones, see: Zhong et al. (2007); Raj et al. (2007); Jimenez-Pulido et al. (2008). For related structures, see: Yehye et al. (2008); Fun, Patil, Jebas et al. (2008); Yang et al. (2008); Ejsmont et al. (2008); Fun, Patil, Rao et al. (2008). For reference bond values, see: Allen et al. (1987).

Experimental top

The compound was prepared by refluxing 2-chloro-5-nitrobenzaldehyde (1.0 mol) with 4-methoxybenzohydrazide (1.0 mol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colourless solid product was filtered, and washed three times with methanol. Colourless block crystals of the title compound were obtained from a methanol solution by slow evaporation in air.

Refinement top

Atom H2 was located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions (C—H = 0.93-0.96 Å) and refined as riding with Uiso(H) = 1.2 Ueq(C) or 1.5Ueq(C) for methyl H atoms. A rotating group model was used for the methyl group.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity.
(E)-N'-(2-Chloro-5-nitrobenzylidene)-4-methoxybenzohydrazide top
Crystal data top
C15H12ClN3O4F(000) = 688
Mr = 333.73Dx = 1.500 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1899 reflections
a = 11.724 (2) Åθ = 2.7–26.0°
b = 13.482 (3) ŵ = 0.28 mm−1
c = 9.4259 (19) ÅT = 298 K
β = 97.199 (3)°Block, colourless
V = 1478.1 (5) Å30.20 × 0.20 × 0.17 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2735 independent reflections
Radiation source: fine-focus sealed tube2320 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→15
Tmin = 0.946, Tmax = 0.953k = −17→14
4284 measured reflectionsl = −12→11
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0432P)2 + 0.2836P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2735 reflectionsΔρmax = 0.14 e Å−3
212 parametersΔρmin = −0.19 e Å−3
3 restraintsAbsolute structure: Flack (1983), 1079 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.01 (7)
Crystal data top
C15H12ClN3O4V = 1478.1 (5) Å3
Mr = 333.73Z = 4
Monoclinic, CcMo Kα radiation
a = 11.724 (2) ŵ = 0.28 mm−1
b = 13.482 (3) ÅT = 298 K
c = 9.4259 (19) Å0.20 × 0.20 × 0.17 mm
β = 97.199 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2735 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2320 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.953Rint = 0.015
4284 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090Δρmax = 0.14 e Å−3
S = 1.04Δρmin = −0.19 e Å−3
2735 reflectionsAbsolute structure: Flack (1983), 1079 Friedel pairs
212 parametersAbsolute structure parameter: −0.01 (7)
3 restraints
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
xyzUiso*/Ueq
Cl10.12621 (9)0.12406 (5)0.37773 (10)0.0861 (3)
N10.13488 (17)0.41377 (14)0.18463 (19)0.0474 (5)
N20.09570 (18)0.49328 (13)0.2558 (2)0.0477 (4)
N30.3330 (2)0.2029 (2)−0.1503 (3)0.0806 (8)
O10.07475 (18)0.58146 (13)0.05053 (18)0.0603 (5)
O2−0.0721 (2)0.92744 (16)0.4294 (3)0.0838 (7)
O30.3489 (3)0.2876 (2)−0.1823 (3)0.1312 (12)
O40.3571 (2)0.1320 (2)−0.2230 (3)0.1006 (8)
C10.1933 (2)0.24746 (17)0.1773 (2)0.0466 (5)
C20.1870 (2)0.15042 (18)0.2246 (3)0.0521 (6)
C30.2269 (2)0.07102 (18)0.1509 (3)0.0625 (7)
H30.22110.00670.18480.075*
C40.2750 (2)0.0880 (2)0.0280 (3)0.0626 (7)
H40.30190.0356−0.02270.075*
C50.2829 (2)0.1836 (2)−0.0190 (3)0.0574 (7)
C60.2439 (2)0.26332 (17)0.0522 (3)0.0506 (6)
H60.25110.32730.01760.061*
C70.1489 (2)0.33260 (16)0.2508 (2)0.0478 (5)
H70.13150.32670.34400.057*
C80.06846 (19)0.57703 (16)0.1789 (2)0.0437 (5)
C90.0312 (2)0.66442 (16)0.2574 (2)0.0432 (5)
C10−0.0184 (2)0.66089 (17)0.3825 (2)0.0466 (5)
H10−0.02770.60010.42620.056*
C11−0.0548 (2)0.7478 (2)0.4443 (3)0.0536 (6)
H11−0.08900.74490.52800.064*
C12−0.0394 (2)0.83779 (18)0.3803 (3)0.0594 (7)
C130.0120 (3)0.8419 (2)0.2577 (3)0.0664 (7)
H130.02430.90310.21660.080*
C140.0454 (2)0.75687 (18)0.1949 (3)0.0576 (7)
H140.07780.76070.10990.069*
C15−0.1293 (3)0.9299 (3)0.5519 (5)0.0924 (11)
H15A−0.19780.89040.53590.139*
H15B−0.14930.99720.57140.139*
H15C−0.07960.90390.63200.139*
H20.085 (2)0.490 (2)0.3482 (13)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1402 (7)0.0565 (4)0.0680 (4)0.0130 (5)0.0377 (4)0.0108 (4)
N10.0625 (12)0.0416 (10)0.0391 (10)0.0010 (8)0.0102 (9)−0.0058 (8)
N20.0704 (12)0.0389 (9)0.0353 (9)0.0033 (8)0.0128 (9)−0.0020 (7)
N30.0738 (16)0.094 (2)0.0798 (18)−0.0181 (14)0.0314 (13)−0.0263 (16)
O10.0928 (13)0.0558 (9)0.0343 (9)0.0018 (9)0.0157 (8)0.0020 (7)
O20.0947 (15)0.0526 (12)0.1063 (18)0.0148 (10)0.0216 (13)−0.0121 (11)
O30.187 (3)0.098 (2)0.131 (2)−0.042 (2)0.109 (2)−0.0274 (17)
O40.1071 (17)0.1107 (19)0.0928 (16)−0.0112 (14)0.0478 (14)−0.0467 (14)
C10.0483 (12)0.0468 (12)0.0440 (13)−0.0013 (10)0.0028 (10)−0.0074 (10)
C20.0607 (15)0.0487 (12)0.0455 (13)0.0046 (11)0.0015 (11)−0.0052 (10)
C30.0749 (17)0.0441 (13)0.0663 (18)0.0083 (12)0.0008 (14)−0.0078 (12)
C40.0590 (15)0.0581 (15)0.0696 (18)0.0076 (12)0.0029 (13)−0.0235 (13)
C50.0464 (14)0.0688 (17)0.0574 (15)−0.0061 (11)0.0080 (12)−0.0217 (13)
C60.0500 (13)0.0504 (13)0.0517 (14)−0.0037 (12)0.0071 (11)−0.0082 (11)
C70.0631 (14)0.0425 (12)0.0379 (12)−0.0009 (11)0.0067 (10)−0.0031 (9)
C80.0553 (13)0.0426 (11)0.0339 (11)−0.0066 (10)0.0085 (9)0.0000 (9)
C90.0510 (13)0.0428 (11)0.0352 (11)0.0004 (10)0.0028 (10)−0.0001 (9)
C100.0563 (14)0.0431 (12)0.0399 (12)−0.0016 (10)0.0046 (11)0.0018 (10)
C110.0512 (13)0.0615 (16)0.0481 (15)0.0030 (12)0.0064 (12)−0.0111 (11)
C120.0589 (15)0.0406 (13)0.0752 (19)0.0073 (11)−0.0051 (14)−0.0043 (12)
C130.0841 (19)0.0430 (13)0.0721 (18)0.0036 (13)0.0099 (15)0.0094 (13)
C140.0753 (17)0.0485 (14)0.0507 (14)−0.0021 (12)0.0144 (13)0.0100 (11)
C150.077 (2)0.081 (2)0.121 (3)0.0114 (16)0.017 (2)−0.038 (2)
Geometric parameters (Å, º) top
Cl1—C21.725 (3)C4—H40.9300
N1—C71.260 (3)C5—C61.376 (3)
N1—N21.374 (2)C6—H60.9300
N2—C81.358 (3)C7—H70.9300
N2—H20.897 (10)C8—C91.485 (3)
N3—O31.202 (4)C9—C101.379 (3)
N3—O41.229 (3)C9—C141.397 (3)
N3—C51.458 (4)C10—C111.399 (3)
O1—C81.223 (3)C10—H100.9300
O2—C121.366 (3)C11—C121.376 (4)
O2—C151.406 (4)C11—H110.9300
C1—C21.387 (3)C12—C131.370 (4)
C1—C61.402 (3)C13—C141.370 (4)
C1—C71.469 (3)C13—H130.9300
C2—C31.389 (3)C14—H140.9300
C3—C41.370 (4)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.369 (4)C15—H15C0.9600
C7—N1—N2117.83 (18)C1—C7—H7120.8
C8—N2—N1117.34 (17)O1—C8—N2121.9 (2)
C8—N2—H2120.9 (19)O1—C8—C9120.8 (2)
N1—N2—H2121.7 (19)N2—C8—C9117.29 (18)
O3—N3—O4123.0 (3)C10—C9—C14118.4 (2)
O3—N3—C5118.3 (3)C10—C9—C8125.4 (2)
O4—N3—C5118.7 (3)C14—C9—C8116.1 (2)
C12—O2—C15118.8 (3)C9—C10—C11120.7 (2)
C2—C1—C6117.3 (2)C9—C10—H10119.7
C2—C1—C7123.4 (2)C11—C10—H10119.7
C6—C1—C7119.3 (2)C12—C11—C10119.5 (2)
C1—C2—C3122.1 (3)C12—C11—H11120.3
C1—C2—Cl1120.45 (19)C10—C11—H11120.3
C3—C2—Cl1117.4 (2)O2—C12—C13114.9 (3)
C4—C3—C2119.6 (3)O2—C12—C11125.0 (3)
C4—C3—H3120.2C13—C12—C11120.1 (2)
C2—C3—H3120.2C14—C13—C12120.7 (2)
C5—C4—C3118.9 (2)C14—C13—H13119.7
C5—C4—H4120.6C12—C13—H13119.7
C3—C4—H4120.6C13—C14—C9120.6 (2)
C4—C5—C6122.5 (3)C13—C14—H14119.7
C4—C5—N3119.5 (2)C9—C14—H14119.7
C6—C5—N3118.0 (3)O2—C15—H15A109.5
C5—C6—C1119.6 (2)O2—C15—H15B109.5
C5—C6—H6120.2H15A—C15—H15B109.5
C1—C6—H6120.2O2—C15—H15C109.5
N1—C7—C1118.5 (2)H15A—C15—H15C109.5
N1—C7—H7120.8H15B—C15—H15C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.90 (1)2.15 (2)2.994 (3)156 (3)
Symmetry code: (i) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H12ClN3O4
Mr333.73
Crystal system, space groupMonoclinic, Cc
Temperature (K)298
a, b, c (Å)11.724 (2), 13.482 (3), 9.4259 (19)
β (°) 97.199 (3)
V (Å3)1478.1 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.28
Crystal size (mm)0.20 × 0.20 × 0.17
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.946, 0.953
No. of measured, independent and
observed [I > 2σ(I)] reflections		4284, 2735, 2320
Rint0.015
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.090, 1.04
No. of reflections2735
No. of parameters212
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.14, −0.19
Absolute structureFlack (1983), 1079 Friedel pairs
Absolute structure parameter−0.01 (7)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.897 (10)2.150 (15)2.994 (3)156 (3)
Symmetry code: (i) x, −y+1, z+1/2.
 

Acknowledgements

Financial support of this work was provided by the Research Foundation of Liaoning Province (project No. 2008470).

References

First citationAllen, 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
 First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationEjsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 64| Part 11| November 2008| Page o2177
doi:10.1107/S1600536808034107
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