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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 67| Part 7| July 2011| Page o1639
doi:10.1107/S160053681102157X

3-Chloro-N′-(2-chloro-5-nitro­benzyl­­idene)­benzohydrazide

Zhen Zhanga*

aExperimental Center, Linyi University, Linyi Shandong 276005, People's Republic of China
*Correspondence e-mail: zhangzhen_lynu@126.com

(Received 30 May 2011; accepted 4 June 2011; online 11 June 2011)

The title mol­ecule, C14H9Cl2N3O3, has an E configuration with respect to the methyl­idene unit. The dihedral angle between the mean planes of the two benzene rings is 12.3 (3)°. In the crystal, mol­ecules are linked via bifurcated N—H⋯(O, N) hydrogen bonds into chains along [001].

Related literature

For the biological applications of hydrazone compounds, see: Ajani et al. (2010[Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.]); Avaji et al. (2009[Avaji, P. G., Kumar, C. H. V., Patil, S. A., Shivananda, K. N. & Nagaraju, C. (2009). Eur. J. Med. Chem. 44, 3552-3559.]); Fan et al. (2010[Fan, C. D., Su, H., Zhao, J., Zhao, B. X., Zhang, S. L. & Miao, J. Y. (2010). Eur. J. Med. Chem. 45, 1438-1446.]); Rasras et al. (2010[Rasras, A. J. M., Al-Tel, T. H., Amal, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307-2313.]). For related hydrazone structures, see: Zhang (2011a[Zhang, Z. (2011a). Acta Cryst. E67, o300.],b[Zhang, Z. (2011b). Acta Cryst. E67, o301.]); Ahmad et al. (2010[Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976.]); Ban (2010[Ban, H.-Y. (2010). Acta Cryst. E66, o3240.]); Ji & Lu (2010[Ji, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, o1514.]); Shalash et al. (2010[Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126-o3127.]).

[Scheme 1]

Experimental

Crystal data

  • C14H9Cl2N3O3

  • Mr = 338.14

  • Monoclinic, P 21 /c

  • a = 7.770 (2) Å

  • b = 24.254 (6) Å

  • c = 7.889 (2) Å

  • β = 95.383 (3)°

  • V = 1480.1 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.45 mm−1

  • T = 298 K

  • 0.32 × 0.30 × 0.30 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.868, Tmax = 0.876

  • 7538 measured reflections

  • 3016 independent reflections

  • 1607 reflections with I > 2σ(I)

  • Rint = 0.055
Refinement

  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.152

  • S = 1.04

  • 3016 reflections

  • 202 parameters

  • 1 restraint

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

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯N1i 0.89 (1) 2.43 (2) 3.139 (4) 137 (3)
N2—H2⋯O3i 0.89 (1) 2.27 (2) 3.095 (4) 154 (3)
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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/S160053681102157X/lh5264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102157X/lh5264Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681102157X/lh5264Isup3.cml

checkCIF report


Comment top

Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Ajani et al., 2010; Avaji et al., 2009; Fan et al., 2010; Rasras et al., 2010). As a continuation of our work related to hydrazone compounds, the crystal structure of the title compound is reported herein.

The molecule is in a E configuration with respect to the methylidene unit (Fig. 1). The bond lengths are comparable to those observed in similar hydrazone compounds (Zhang, 2011a,b; Ahmad et al., 2010; Ban, 2010; Ji & Lu, 2010; Shalash et al., 2010). The dihedral angle between the mean planes of the two benzene rings is 12.3 (3)°. In the crystal, molecules are linked via bifurcated N—H···(O, N) hydrogen bonds to from chains along [001] (Table 1, Fig. 2).

Related literature top

For the biological applications of hydrazone compounds, see: Ajani et al. (2010); Avaji et al. (2009); Fan et al. (2010); Rasras et al. (2010). For related hydrazone structures, see: Zhang (2011a,b); Ahmad et al. (2010); Ban (2010); Ji & Lu (2010); Shalash et al. (2010).

Experimental top

A methanol solution (50 ml) of 3-chlorobenzohydrazide (0.01 mol) and 2-chloro-5-nitrobenzaldehyde (0.01 mol) was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals suitable for X-ray diffraction were formed by slow evaporation of the solution in air.

Refinement top

The amino atom, H2, was located in 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 refined using the riding-model approximation, with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. The packing of the title compound. Hydrogen bonds are shown as dashed lines. Only H atoms involved in hydrogen bonds are shown.
3-Chloro-N'-(2-chloro-5-nitrobenzylidene)benzohydrazide top
Crystal data top
C14H9Cl2N3O3F(000) = 688
Mr = 338.14Dx = 1.517 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 814 reflections
a = 7.770 (2) Åθ = 2.6–24.5°
b = 24.254 (6) ŵ = 0.45 mm−1
c = 7.889 (2) ÅT = 298 K
β = 95.383 (3)°Block, yellow
V = 1480.1 (7) Å30.32 × 0.30 × 0.30 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		3016 independent reflections
Radiation source: fine-focus sealed tube1607 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω scansθmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −5→9
Tmin = 0.868, Tmax = 0.876k = −30→30
7538 measured reflectionsl = −9→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.2711P]
where P = (Fo2 + 2Fc2)/3
3016 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.23 e Å−3
1 restraintΔρmin = −0.24 e Å−3
Crystal data top
C14H9Cl2N3O3V = 1480.1 (7) Å3
Mr = 338.14Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.770 (2) ŵ = 0.45 mm−1
b = 24.254 (6) ÅT = 298 K
c = 7.889 (2) Å0.32 × 0.30 × 0.30 mm
β = 95.383 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer		3016 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		1607 reflections with I > 2σ(I)
Tmin = 0.868, Tmax = 0.876Rint = 0.055
7538 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0601 restraint
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.23 e Å−3
3016 reflectionsΔρmin = −0.24 e Å−3
202 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cl10.33815 (15)0.55819 (4)0.48098 (13)0.0786 (4)
Cl20.02262 (16)0.99758 (4)0.26818 (14)0.0827 (4)
N10.2837 (3)0.72544 (12)0.6153 (3)0.0429 (7)
N20.1950 (4)0.75727 (12)0.4918 (3)0.0459 (7)
N30.6550 (5)0.65111 (19)1.1284 (4)0.0771 (11)
O10.7009 (5)0.61872 (16)1.2395 (4)0.1306 (15)
O20.6670 (5)0.70061 (16)1.1441 (4)0.1060 (12)
O30.1450 (4)0.82247 (10)0.6847 (3)0.0701 (8)
C10.4302 (4)0.64304 (14)0.6916 (4)0.0425 (8)
C20.4361 (4)0.58649 (14)0.6668 (4)0.0493 (9)
C30.5135 (5)0.55147 (15)0.7884 (5)0.0591 (10)
H30.51660.51370.76810.071*
C40.5859 (5)0.57270 (16)0.9396 (5)0.0602 (10)
H40.63750.54951.02350.072*
C50.5812 (4)0.62850 (16)0.9653 (4)0.0513 (9)
C60.5069 (4)0.66400 (14)0.8457 (4)0.0464 (9)
H60.50730.70170.86650.056*
C70.3405 (4)0.67978 (15)0.5662 (4)0.0469 (9)
H70.32520.66980.45190.056*
C80.1301 (5)0.80617 (14)0.5386 (4)0.0467 (9)
C90.0426 (4)0.83855 (13)0.3958 (4)0.0427 (8)
C100.0624 (4)0.89538 (14)0.4003 (4)0.0475 (9)
H100.12240.91230.49380.057*
C11−0.0076 (5)0.92655 (15)0.2651 (4)0.0520 (9)
C12−0.1003 (5)0.90243 (17)0.1273 (5)0.0587 (10)
H12−0.14590.92390.03620.070*
C13−0.1246 (5)0.84646 (16)0.1259 (4)0.0574 (10)
H13−0.18910.83000.03420.069*
C14−0.0544 (4)0.81411 (15)0.2593 (4)0.0472 (9)
H14−0.07200.77620.25760.057*
H20.193 (4)0.7439 (12)0.386 (2)0.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0933 (9)0.0746 (7)0.0636 (7)0.0081 (6)−0.0147 (6)−0.0264 (6)
Cl20.1195 (10)0.0564 (7)0.0692 (7)0.0114 (6)−0.0070 (7)0.0126 (5)
N10.0476 (17)0.0491 (17)0.0306 (15)0.0043 (14)−0.0040 (13)0.0048 (13)
N20.0595 (19)0.0541 (19)0.0229 (14)0.0092 (15)−0.0032 (13)0.0008 (13)
N30.084 (3)0.092 (3)0.050 (2)0.005 (2)−0.0218 (19)0.002 (2)
O10.195 (4)0.126 (3)0.058 (2)0.012 (3)−0.058 (2)0.018 (2)
O20.134 (3)0.094 (3)0.080 (2)0.007 (2)−0.044 (2)−0.024 (2)
O30.114 (2)0.0647 (17)0.0285 (13)0.0229 (16)−0.0129 (14)−0.0066 (12)
C10.041 (2)0.051 (2)0.0342 (18)0.0037 (16)−0.0001 (15)−0.0010 (15)
C20.051 (2)0.054 (2)0.041 (2)0.0050 (18)−0.0016 (17)−0.0074 (17)
C30.070 (3)0.047 (2)0.060 (3)0.0069 (19)0.001 (2)0.0013 (18)
C40.066 (3)0.061 (3)0.052 (2)0.008 (2)−0.003 (2)0.013 (2)
C50.048 (2)0.064 (3)0.039 (2)0.0007 (18)−0.0092 (17)0.0020 (18)
C60.046 (2)0.052 (2)0.040 (2)0.0069 (17)−0.0018 (17)−0.0033 (16)
C70.054 (2)0.056 (2)0.0293 (18)0.0050 (19)−0.0023 (16)−0.0036 (16)
C80.056 (2)0.049 (2)0.034 (2)0.0029 (18)−0.0014 (17)0.0023 (16)
C90.047 (2)0.052 (2)0.0289 (18)0.0104 (17)−0.0008 (15)0.0027 (15)
C100.058 (2)0.054 (2)0.0304 (19)0.0052 (18)−0.0012 (16)−0.0006 (16)
C110.060 (2)0.055 (2)0.040 (2)0.0103 (19)0.0020 (18)0.0079 (17)
C120.060 (3)0.074 (3)0.040 (2)0.018 (2)−0.0058 (19)0.0102 (19)
C130.061 (2)0.074 (3)0.034 (2)0.010 (2)−0.0105 (18)−0.0010 (19)
C140.049 (2)0.055 (2)0.0365 (19)0.0067 (17)0.0002 (17)−0.0011 (16)
Geometric parameters (Å, º) top
Cl1—C21.729 (3)C4—C51.370 (5)
Cl2—C111.738 (4)C4—H40.9300
N1—C71.266 (4)C5—C61.365 (4)
N1—N21.376 (3)C6—H60.9300
N2—C81.354 (4)C7—H70.9300
N2—H20.893 (10)C8—C91.485 (4)
N3—O11.206 (4)C9—C101.387 (4)
N3—O21.210 (4)C9—C141.388 (4)
N3—C51.465 (5)C10—C111.377 (4)
O3—C81.214 (4)C10—H100.9300
C1—C21.387 (5)C11—C121.377 (5)
C1—C61.398 (4)C12—C131.371 (5)
C1—C71.460 (4)C12—H120.9300
C2—C31.377 (5)C13—C141.383 (4)
C3—C41.371 (5)C13—H130.9300
C3—H30.9300C14—H140.9300
C7—N1—N2116.1 (3)N1—C7—C1119.0 (3)
C8—N2—N1118.2 (3)N1—C7—H7120.5
C8—N2—H2127 (2)C1—C7—H7120.5
N1—N2—H2115 (2)O3—C8—N2122.7 (3)
O1—N3—O2123.9 (4)O3—C8—C9123.0 (3)
O1—N3—C5117.3 (4)N2—C8—C9114.3 (3)
O2—N3—C5118.8 (3)C10—C9—C14119.7 (3)
C2—C1—C6117.7 (3)C10—C9—C8117.7 (3)
C2—C1—C7121.9 (3)C14—C9—C8122.6 (3)
C6—C1—C7120.3 (3)C11—C10—C9119.4 (3)
C3—C2—C1122.0 (3)C11—C10—H10120.3
C3—C2—Cl1118.3 (3)C9—C10—H10120.3
C1—C2—Cl1119.7 (3)C12—C11—C10121.2 (4)
C4—C3—C2119.4 (3)C12—C11—Cl2119.5 (3)
C4—C3—H3120.3C10—C11—Cl2119.4 (3)
C2—C3—H3120.3C13—C12—C11119.3 (3)
C5—C4—C3119.1 (3)C13—C12—H12120.4
C5—C4—H4120.5C11—C12—H12120.4
C3—C4—H4120.5C12—C13—C14120.8 (3)
C6—C5—C4122.4 (3)C12—C13—H13119.6
C6—C5—N3118.5 (4)C14—C13—H13119.6
C4—C5—N3119.1 (3)C13—C14—C9119.7 (3)
C5—C6—C1119.3 (3)C13—C14—H14120.2
C5—C6—H6120.3C9—C14—H14120.2
C1—C6—H6120.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.89 (1)2.43 (2)3.139 (4)137 (3)
N2—H2···O3i0.89 (1)2.27 (2)3.095 (4)154 (3)
Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC14H9Cl2N3O3
Mr338.14
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)7.770 (2), 24.254 (6), 7.889 (2)
β (°) 95.383 (3)
V (Å3)1480.1 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.45
Crystal size (mm)0.32 × 0.30 × 0.30
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.868, 0.876
No. of measured, independent and
observed [I > 2σ(I)] reflections		7538, 3016, 1607
Rint0.055
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.152, 1.04
No. of reflections3016
No. of parameters202
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.23, −0.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.893 (10)2.43 (2)3.139 (4)137 (3)
N2—H2···O3i0.893 (10)2.267 (17)3.095 (4)154 (3)
Symmetry code: (i) x, −y+3/2, z−1/2.
 

Acknowledgements

The author acknowledges the Experimental Center of Linyi University for supporting this work.

References

First citationAhmad, 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
 First citationAjani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214–221.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationAvaji, P. G., Kumar, C. H. V., Patil, S. A., Shivananda, K. N. & Nagaraju, C. (2009). Eur. J. Med. Chem. 44, 3552–3559.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBan, H.-Y. (2010). Acta Cryst. E66, o3240.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationJi, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, o1514.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRasras, A. J. M., Al-Tel, T. H., Amal, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307–2313.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationShalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126–o3127.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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 First citationZhang, Z. (2011b). Acta Cryst. E67, o301.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 7| July 2011| Page o1639
doi:10.1107/S160053681102157X
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