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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 66| Part 2| February 2010| Page o290
https://doi.org/10.1107/S1600536809055330

2-Chloro-N′-(4-nitro­benzyl­­idene)benzo­hydrazide

Cong-Shan Zhoua and Tao Yanga*

aCollege of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan 414006, People's Republic of China
*Correspondence e-mail: zhoucongsh@gmail.com

(Received 23 December 2009; accepted 24 December 2009; online 9 January 2010)

The title Schiff base compound, C14H10ClN3O3, exists in a trans configuration with respect to the C=N bond. The dihedral angle between the two benzene rings is 15.9 (2)°. In the crystal, the mol­ecules are linked into chains along [101] by inter­molecular N—H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff bases, see: Mohamed et al. (2009[Mohamed, G. G., Omar, M. M. & Ibrahim, A. A. (2009). Eur. J. Med. Chem. 44, 4801-4812.]); Ritter et al. (2009[Ritter, E., Przybylski, P., Brzezinski, B. & Bartl, F. (2009). Curr. Org. Chem. 13, 241-249.]); Bagihalli et al. (2008[Bagihalli, G. B., Avaji, P. G., Patil, S. A. & Badami, P. S. (2008). Eur. J. Med. Chem. 43, 2639-2649.]). For the crystal structures of Schiff base compounds, see: Fun et al. (2008[Fun, H.-K., Chantrapromma, S., Jana, S., Hazra, A. & Goswami, S. (2008). Acta Cryst. E64, o175-o176.]); Shafiq et al. (2009[Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2501.]); Goh et al. (2010[Goh, J. H., Fun, H.-K., Vinayaka, A. C. & Kalluraya, B. (2010). Acta Cryst. E66, o24.]). For other related structures, see: Zhou et al. (2009[Zhou, C.-S., Hou, H.-Y. & Yang, T. (2009). Z. Kristallogr. New Cryst. Struct. 224, 37-38.]); Zhou & Yang (2009[Zhou, C.-S. & Yang, T. (2009). Z. Kristallogr. New Cryst. Struct. 224, 39-40.]).

[Scheme 1]

Experimental

Crystal data

  • C14H10ClN3O3

  • Mr = 303.70

  • Monoclinic, P 21 /n

  • a = 7.2752 (3) Å

  • b = 26.4081 (9) Å

  • c = 7.7284 (3) Å

  • β = 113.000 (2)°

  • V = 1366.78 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 298 K

  • 0.23 × 0.20 × 0.20 mm
Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.936, Tmax = 0.944

  • 7876 measured reflections

  • 2763 independent reflections

  • 1934 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.113

  • S = 1.03

  • 2763 reflections

  • 193 parameters

  • 1 restraint

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

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2A⋯O3i 0.90 (1) 1.97 (1) 2.855 (2) 169 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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: https://doi.org/10.1107/S1600536809055330/ci5003sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055330/ci5003Isup2.hkl

checkCIF report


Comment top

Schiff bases are a kind of interesting compounds, which possess excellent biological properties, such as antibacterial, antimicrobial, and antitumor (Mohamed et al., 2009; Ritter et al., 2009; Bagihalli et al., 2008). Recently, a large number of Schiff bases derived from the reaction of aldehydes with benzohydrazides have been reported (Fun et al., 2008; Shafiq et al., 2009; Goh et al., 2010). In this paper, the crystal structure of the title new Schiff base compound is reported.

In the title compound (Fig. 1), bond lengths are comparable with those observed in related structures (Zhou et al., 2009; Zhou & Yang, 2009). The molecule exists in a trans configuration with respect to the acyclic C═N bond. The molecule is distorted from planarity, with a dihedral angle between the two benzene rings of 15.9 (2)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds link adjacent molecules into chains along the [101] (Table 1 and Fig. 2).

Related literature top

For the biological properties of Schiff bases, see: Mohamed et al. (2009); Ritter et al. (2009); Bagihalli et al. (2008). For the crystal structures of Schiff base compounds, see: Fun et al. (2008); Shafiq et al. (2009); Goh et al. (2010). For related structures, see: Zhou et al. (2009); Zhou & Yang (2009).

Experimental top

4-Nitrobenzaldehyde (1.0 mmol, 151.0 mg) and 2-chlorobenzohydrazide (1.0 mmol, 170.0 mg) were dissolved in methanol (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was left in air for a few days, yielding colourless block-shaped crystals.

Refinement top

Atom H2A was located in a difference map and refined with a N–H distance restraint of 0.90 (1) Å and Uiso(H) = 0.08 Å2. The remaining H atoms were positioned geometrically (C–H = 0.93 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Structure description top

Schiff bases are a kind of interesting compounds, which possess excellent biological properties, such as antibacterial, antimicrobial, and antitumor (Mohamed et al., 2009; Ritter et al., 2009; Bagihalli et al., 2008). Recently, a large number of Schiff bases derived from the reaction of aldehydes with benzohydrazides have been reported (Fun et al., 2008; Shafiq et al., 2009; Goh et al., 2010). In this paper, the crystal structure of the title new Schiff base compound is reported.

In the title compound (Fig. 1), bond lengths are comparable with those observed in related structures (Zhou et al., 2009; Zhou & Yang, 2009). The molecule exists in a trans configuration with respect to the acyclic C═N bond. The molecule is distorted from planarity, with a dihedral angle between the two benzene rings of 15.9 (2)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds link adjacent molecules into chains along the [101] (Table 1 and Fig. 2).

For the biological properties of Schiff bases, see: Mohamed et al. (2009); Ritter et al. (2009); Bagihalli et al. (2008). For the crystal structures of Schiff base compounds, see: Fun et al. (2008); Shafiq et al. (2009); Goh et al. (2010). For related structures, see: Zhou et al. (2009); Zhou & Yang (2009).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.
2-Chloro-N'-(4-nitrobenzylidene)benzohydrazide top
Crystal data top
C14H10ClN3O3F(000) = 624
Mr = 303.70Dx = 1.476 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1518 reflections
a = 7.2752 (3) Åθ = 2.4–24.5°
b = 26.4081 (9) ŵ = 0.29 mm−1
c = 7.7284 (3) ÅT = 298 K
β = 113.000 (2)°Block, colourless
V = 1366.78 (9) Å30.23 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2763 independent reflections
Radiation source: fine-focus sealed tube1934 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 26.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.936, Tmax = 0.944k = −29→32
7876 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.233P]
where P = (Fo2 + 2Fc2)/3
2763 reflections(Δ/σ)max = 0.003
193 parametersΔρmax = 0.19 e Å−3
1 restraintΔρmin = −0.27 e Å−3
Crystal data top
C14H10ClN3O3V = 1366.78 (9) Å3
Mr = 303.70Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.2752 (3) ŵ = 0.29 mm−1
b = 26.4081 (9) ÅT = 298 K
c = 7.7284 (3) Å0.23 × 0.20 × 0.20 mm
β = 113.000 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2763 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1934 reflections with I > 2σ(I)
Tmin = 0.936, Tmax = 0.944Rint = 0.036
7876 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.19 e Å−3
2763 reflectionsΔρmin = −0.27 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
xyzUiso*/Ueq
Cl10.25382 (9)0.09582 (2)0.73742 (9)0.0617 (2)
N10.2283 (2)0.28721 (7)0.5887 (2)0.0434 (4)
N20.2675 (2)0.25629 (7)0.7434 (2)0.0437 (4)
N30.2493 (3)0.47567 (8)0.0679 (3)0.0637 (6)
O10.2747 (4)0.52006 (8)0.1124 (3)0.1069 (8)
O20.2156 (4)0.46052 (8)−0.0899 (3)0.0983 (7)
O30.0453 (2)0.19654 (5)0.57474 (19)0.0498 (4)
C10.2747 (3)0.36895 (8)0.4821 (3)0.0388 (5)
C20.3001 (3)0.42028 (8)0.5248 (3)0.0505 (6)
H20.32470.43110.64640.061*
C30.2892 (3)0.45526 (8)0.3895 (3)0.0525 (6)
H30.30320.48960.41760.063*
C40.2573 (3)0.43846 (8)0.2119 (3)0.0447 (5)
C50.2344 (3)0.38808 (8)0.1647 (3)0.0469 (5)
H50.21430.37760.04380.056*
C60.2420 (3)0.35350 (8)0.3006 (3)0.0443 (5)
H60.22490.31930.27040.053*
C70.2910 (3)0.33266 (8)0.6288 (3)0.0435 (5)
H70.34800.34270.75410.052*
C80.1706 (3)0.21195 (8)0.7239 (3)0.0396 (5)
C90.2232 (3)0.18436 (8)0.9059 (3)0.0392 (5)
C100.2608 (3)0.13269 (8)0.9245 (3)0.0452 (5)
C110.3086 (3)0.10918 (10)1.0973 (4)0.0612 (7)
H110.33990.07491.11080.073*
C120.3095 (4)0.13687 (12)1.2487 (4)0.0680 (8)
H120.33720.12071.36310.082*
C130.2705 (4)0.18759 (11)1.2333 (3)0.0623 (7)
H130.27220.20581.33690.075*
C140.2289 (3)0.21163 (9)1.0648 (3)0.0496 (6)
H140.20420.24631.05530.060*
H2A0.359 (3)0.2671 (9)0.853 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0603 (4)0.0542 (4)0.0718 (4)0.0013 (3)0.0270 (3)−0.0108 (3)
N10.0437 (10)0.0494 (11)0.0319 (9)−0.0017 (8)0.0091 (7)0.0068 (8)
N20.0462 (10)0.0469 (10)0.0281 (9)−0.0076 (8)0.0039 (7)0.0049 (8)
N30.0825 (15)0.0591 (14)0.0531 (13)0.0030 (11)0.0302 (11)0.0129 (11)
O10.197 (3)0.0488 (12)0.0902 (16)−0.0089 (14)0.0720 (17)0.0117 (11)
O20.160 (2)0.0860 (15)0.0546 (12)−0.0099 (14)0.0489 (13)0.0119 (11)
O30.0535 (9)0.0502 (9)0.0318 (8)−0.0070 (7)0.0017 (7)0.0008 (7)
C10.0362 (10)0.0422 (12)0.0357 (11)0.0003 (9)0.0117 (9)0.0005 (9)
C20.0632 (14)0.0485 (13)0.0383 (12)−0.0032 (11)0.0182 (10)−0.0059 (10)
C30.0667 (15)0.0382 (12)0.0521 (14)−0.0037 (10)0.0228 (11)−0.0026 (10)
C40.0457 (12)0.0454 (12)0.0444 (12)0.0019 (10)0.0190 (10)0.0082 (10)
C50.0524 (13)0.0518 (13)0.0360 (11)0.0026 (11)0.0167 (10)−0.0014 (10)
C60.0502 (12)0.0402 (11)0.0407 (12)0.0004 (9)0.0156 (10)−0.0030 (10)
C70.0436 (12)0.0493 (13)0.0337 (11)−0.0019 (10)0.0108 (9)−0.0021 (9)
C80.0395 (11)0.0454 (12)0.0303 (10)0.0019 (9)0.0096 (9)0.0013 (9)
C90.0333 (10)0.0472 (13)0.0329 (10)−0.0032 (9)0.0084 (8)0.0005 (9)
C100.0351 (11)0.0488 (13)0.0479 (13)−0.0033 (9)0.0120 (9)0.0057 (10)
C110.0505 (14)0.0609 (16)0.0635 (16)−0.0018 (11)0.0129 (12)0.0220 (13)
C120.0601 (15)0.090 (2)0.0450 (15)−0.0131 (14)0.0106 (12)0.0225 (15)
C130.0604 (15)0.089 (2)0.0369 (13)−0.0178 (14)0.0182 (11)−0.0050 (13)
C140.0478 (12)0.0586 (14)0.0399 (12)−0.0076 (11)0.0145 (10)0.0018 (11)
Geometric parameters (Å, º) top
Cl1—C101.727 (2)C4—C51.372 (3)
N1—C71.278 (3)C5—C61.377 (3)
N1—N21.382 (2)C5—H50.93
N2—C81.344 (3)C6—H60.93
N2—H2A0.895 (10)C7—H70.93
N3—O21.214 (3)C8—C91.495 (3)
N3—O11.215 (3)C9—C101.388 (3)
N3—C41.468 (3)C9—C141.410 (3)
O3—C81.226 (2)C10—C111.388 (3)
C1—C61.389 (3)C11—C121.378 (4)
C1—C21.390 (3)C11—H110.93
C1—C71.454 (3)C12—C131.365 (4)
C2—C31.374 (3)C12—H120.93
C2—H20.93C13—C141.372 (3)
C3—C41.373 (3)C13—H130.93
C3—H30.93C14—H140.93
C7—N1—N2114.29 (16)N1—C7—C1121.13 (18)
C8—N2—N1119.69 (15)N1—C7—H7119.4
C8—N2—H2A123.1 (17)C1—C7—H7119.4
N1—N2—H2A117.2 (17)O3—C8—N2124.00 (18)
O2—N3—O1123.4 (2)O3—C8—C9123.06 (18)
O2—N3—C4118.2 (2)N2—C8—C9112.86 (16)
O1—N3—C4118.3 (2)C10—C9—C14118.30 (18)
C6—C1—C2118.74 (19)C10—C9—C8122.97 (18)
C6—C1—C7121.58 (19)C14—C9—C8118.69 (18)
C2—C1—C7119.64 (19)C11—C10—C9120.3 (2)
C3—C2—C1120.8 (2)C11—C10—Cl1117.86 (19)
C3—C2—H2119.6C9—C10—Cl1121.83 (16)
C1—C2—H2119.6C12—C11—C10119.7 (2)
C4—C3—C2118.7 (2)C12—C11—H11120.1
C4—C3—H3120.6C10—C11—H11120.1
C2—C3—H3120.6C13—C12—C11121.0 (2)
C5—C4—C3122.3 (2)C13—C12—H12119.5
C5—C4—N3118.8 (2)C11—C12—H12119.5
C3—C4—N3118.8 (2)C12—C13—C14119.9 (2)
C4—C5—C6118.4 (2)C12—C13—H13120.1
C4—C5—H5120.8C14—C13—H13120.1
C6—C5—H5120.8C13—C14—C9120.7 (2)
C5—C6—C1121.0 (2)C13—C14—H14119.6
C5—C6—H6119.5C9—C14—H14119.6
C1—C6—H6119.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.90 (1)1.97 (1)2.855 (2)169 (2)
Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H10ClN3O3
Mr303.70
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.2752 (3), 26.4081 (9), 7.7284 (3)
β (°) 113.000 (2)
V (Å3)1366.78 (9)
Z4
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.23 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.936, 0.944
No. of measured, independent and
observed [I > 2σ(I)] reflections		7876, 2763, 1934
Rint0.036
(sin θ/λ)max (Å−1)0.624
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.113, 1.03
No. of reflections2763
No. of parameters193
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.19, −0.27

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.895 (10)1.971 (11)2.855 (2)169 (2)
Symmetry code: (i) x+1/2, −y+1/2, z+1/2.
 

Acknowledgements

This work was supported by the Hunan Provincial Natural Science Foundation of China (grant No. 09 J J6022) and the Scientific Research Fund of Hunan Provincial Education Department, China (grant No. 08B031).

References

First citationBagihalli, G. B., Avaji, P. G., Patil, S. A. & Badami, P. S. (2008). Eur. J. Med. Chem. 43, 2639–2649.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFun, H.-K., Chantrapromma, S., Jana, S., Hazra, A. & Goswami, S. (2008). Acta Cryst. E64, o175–o176.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGoh, J. H., Fun, H.-K., Vinayaka, A. C. & Kalluraya, B. (2010). Acta Cryst. E66, o24.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationMohamed, G. G., Omar, M. M. & Ibrahim, A. A. (2009). Eur. J. Med. Chem. 44, 4801–4812.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRitter, E., Przybylski, P., Brzezinski, B. & Bartl, F. (2009). Curr. Org. Chem. 13, 241–249.  Web of Science CrossRef CAS Google Scholar
 First citationShafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2501.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZhou, C.-S., Hou, H.-Y. & Yang, T. (2009). Z. Kristallogr. New Cryst. Struct. 224, 37–38.  CAS Google Scholar
 First citationZhou, C.-S. & Yang, T. (2009). Z. Kristallogr. New Cryst. Struct. 224, 39–40.  CAS Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Page o290
https://doi.org/10.1107/S1600536809055330
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