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

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(E)-4-Chloro-N′-(2-chloro­benzyl­­idene)benzohydrazide

aDepartment of Chemistry, Ankang University, Ankang Shanxi 725000, People's Republic of China
*Correspondence e-mail: guobiao_cao@126.com

(Received 24 August 2009; accepted 4 September 2009; online 9 September 2009)

The title compound, C14H10Cl2N2O, was synthesized by the reaction of 2-chloro­benzaldehyde with an equimolar quantity of 4-chloro­benzohydrazide in methanol. The mol­ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 8.6 (2)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009[Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189.]); Fun et al. (2008[Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.]); Li & Ban (2009[Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o1466.]); Zhu et al. (2009[Zhu, C.-G., Wei, Y.-J. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o85.]); Yang (2007[Yang, D.-S. (2007). J. Chem. Crystallogr. 37, 343-348.]); You et al. (2008[You, Z.-L., Dai, W.-M., Xu, X.-Q. & Hu, Y.-Q. (2008). Pol. J. Chem. 82, 2215-2219.]). For the hydrazone compounds previously reported by our group, see: Qu et al. (2008[Qu, L.-Z., Yang, T., Cao, G.-B. & Wang, X.-Y. (2008). Acta Cryst. E64, o2061.]); Yang et al. (2008[Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186.]), Cao & Lu (2009a[Cao, G.-B. & Lu, X.-H. (2009a). Acta Cryst. E65, o1587.],b[Cao, G.-B. & Lu, X.-H. (2009b). Acta Cryst. E65, o1600.]), Cao (2009a[Cao, G.-B. (2009a). Acta Cryst. E65, o2085.],b[Cao, G.-B. (2009b). Acta Cryst. E65, o2086.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10Cl2N2O

  • Mr = 293.14

  • Monoclinic, P 21 /c

  • a = 10.9140 (4) Å

  • b = 13.3253 (4) Å

  • c = 9.1283 (3) Å

  • β = 96.165 (2)°

  • V = 1319.87 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.48 mm−1

  • T = 298 K

  • 0.20 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART 1K diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.910, Tmax = 0.918

  • 7970 measured reflections

  • 2863 independent reflections

  • 2099 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.103

  • S = 1.05

  • 2863 reflections

  • 176 parameters

  • 1 restraint

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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O1i 0.889 (9) 2.065 (11) 2.9157 (18) 159.8 (18)
Symmetry code: (i) [x, -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


Comment top

In the last few years, the crystal structures of a large number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008; Cao & Lu, 2009a,b; Cao, 2009a,b), the title new hydrazone compound, derived from the reaction of 2-chlorobenzaldehyde with an equimolar quantity of 4-chlorobenzohydrazide, is reported.

In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 8.6 (2)°. The molecule displays an E configuration about the CN bond. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds, Table 1, to form chains running along the c axis, Fig. 2.

Related literature top

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009); Fun et al. (2008); Li & Ban (2009); Zhu et al. (2009); Yang (2007); You et al. (2008). For the hydrazone compounds previously reported by our group, see: Qu et al. (2008); Yang et al. (2008), Cao & Lu (2009a,b), Cao (2009a,b).

Experimental top

The compound was prepared by refluxing equimolar quantities of 2-chlorobenzaldehyde with 4-chlorobenzohydrazide in methanol. Colorless block-like crystals were formed by slow evaporation of the solution in air.

Refinement top

H2 was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. The other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93 Å, and with Uiso(H) set at 1.2Ueq(C).

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 ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of the title compound, viewed along the b axis. Hydrogen bonds are drawn as dashed lines.
(E)-4-Chloro-N'-(2-chlorobenzylidene)benzohydrazide top
Crystal data top
C14H10Cl2N2OF(000) = 600
Mr = 293.14Dx = 1.475 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2259 reflections
a = 10.9140 (4) Åθ = 2.4–26.5°
b = 13.3253 (4) ŵ = 0.48 mm1
c = 9.1283 (3) ÅT = 298 K
β = 96.165 (2)°Block, colorless
V = 1319.87 (8) Å30.20 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART 1K
diffractometer
2863 independent reflections
Radiation source: fine-focus sealed tube2099 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1013
Tmin = 0.910, Tmax = 0.918k = 1716
7970 measured reflectionsl = 1111
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.3326P]
where P = (Fo2 + 2Fc2)/3
2863 reflections(Δ/σ)max = 0.001
176 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = 0.23 e Å3
Crystal data top
C14H10Cl2N2OV = 1319.87 (8) Å3
Mr = 293.14Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.9140 (4) ŵ = 0.48 mm1
b = 13.3253 (4) ÅT = 298 K
c = 9.1283 (3) Å0.20 × 0.20 × 0.18 mm
β = 96.165 (2)°
Data collection top
Bruker SMART 1K
diffractometer
2863 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2099 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 0.918Rint = 0.023
7970 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.18 e Å3
2863 reflectionsΔρmin = 0.23 e Å3
176 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
Cl10.23751 (6)0.62666 (4)1.13145 (6)0.0669 (2)
Cl20.45481 (6)0.17289 (4)1.34138 (7)0.0725 (2)
N10.19376 (14)0.33512 (10)0.93524 (16)0.0400 (4)
N20.23897 (15)0.25647 (11)1.02386 (16)0.0394 (4)
O10.27146 (14)0.16448 (10)0.82336 (13)0.0503 (4)
C10.13324 (16)0.50527 (13)0.9130 (2)0.0404 (4)
C20.15065 (18)0.60340 (14)0.9639 (2)0.0442 (4)
C30.1036 (2)0.68464 (15)0.8830 (2)0.0543 (5)
H30.11660.74940.91930.065*
C40.0371 (2)0.66901 (17)0.7480 (3)0.0600 (6)
H40.00480.72340.69290.072*
C50.0185 (2)0.57327 (17)0.6945 (2)0.0586 (6)
H50.02630.56300.60320.070*
C60.06591 (18)0.49246 (15)0.7758 (2)0.0487 (5)
H60.05270.42800.73830.058*
C70.18227 (18)0.41876 (13)0.9994 (2)0.0423 (4)
H70.20480.42501.10020.051*
C80.27714 (17)0.17307 (13)0.95759 (19)0.0376 (4)
C90.32468 (17)0.08966 (12)1.05677 (18)0.0359 (4)
C100.37559 (18)0.10432 (13)1.20078 (19)0.0411 (4)
H100.38120.16881.23990.049*
C110.41803 (19)0.02376 (14)1.2864 (2)0.0477 (5)
H110.45370.03401.38240.057*
C120.40759 (18)0.07139 (14)1.2298 (2)0.0456 (5)
C130.3595 (2)0.08810 (14)1.0865 (2)0.0570 (6)
H130.35410.15291.04840.068*
C140.3195 (2)0.00707 (14)1.0001 (2)0.0521 (5)
H140.28850.01740.90230.063*
H20.2458 (17)0.2649 (15)1.1210 (11)0.048 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0997 (5)0.0446 (3)0.0528 (3)0.0018 (3)0.0077 (3)0.0010 (2)
Cl20.0851 (5)0.0532 (3)0.0794 (4)0.0270 (3)0.0106 (3)0.0243 (3)
N10.0515 (9)0.0326 (8)0.0350 (8)0.0001 (6)0.0009 (7)0.0062 (6)
N20.0597 (10)0.0302 (7)0.0272 (7)0.0026 (7)0.0002 (7)0.0020 (6)
O10.0832 (10)0.0410 (7)0.0264 (6)0.0001 (6)0.0039 (6)0.0008 (5)
C10.0451 (11)0.0377 (9)0.0397 (10)0.0033 (8)0.0101 (8)0.0068 (8)
C20.0504 (11)0.0396 (10)0.0434 (10)0.0023 (8)0.0084 (8)0.0055 (8)
C30.0655 (14)0.0364 (10)0.0616 (13)0.0059 (9)0.0098 (11)0.0081 (9)
C40.0627 (14)0.0519 (13)0.0652 (14)0.0149 (10)0.0053 (11)0.0224 (11)
C50.0607 (14)0.0623 (14)0.0506 (12)0.0105 (11)0.0043 (10)0.0106 (10)
C60.0542 (12)0.0436 (11)0.0478 (11)0.0055 (9)0.0029 (9)0.0033 (9)
C70.0573 (12)0.0348 (9)0.0347 (9)0.0020 (8)0.0049 (8)0.0045 (7)
C80.0491 (11)0.0331 (9)0.0301 (9)0.0065 (7)0.0014 (8)0.0004 (7)
C90.0449 (10)0.0305 (8)0.0328 (9)0.0012 (7)0.0057 (7)0.0004 (7)
C100.0544 (12)0.0331 (9)0.0354 (10)0.0001 (8)0.0023 (8)0.0028 (7)
C110.0595 (13)0.0460 (11)0.0363 (10)0.0074 (9)0.0007 (9)0.0030 (8)
C120.0494 (11)0.0381 (10)0.0500 (11)0.0111 (8)0.0088 (9)0.0102 (8)
C130.0808 (16)0.0299 (9)0.0596 (13)0.0065 (10)0.0046 (11)0.0057 (9)
C140.0780 (15)0.0385 (10)0.0379 (11)0.0037 (10)0.0026 (9)0.0079 (8)
Geometric parameters (Å, º) top
Cl1—C21.739 (2)C5—C61.377 (3)
Cl2—C121.7379 (19)C5—H50.9300
N1—C71.272 (2)C6—H60.9300
N1—N21.3822 (19)C7—H70.9300
N2—C81.352 (2)C8—C91.491 (2)
N2—H20.889 (9)C9—C101.385 (2)
O1—C81.225 (2)C9—C141.388 (2)
C1—C61.393 (3)C10—C111.378 (2)
C1—C21.394 (3)C10—H100.9300
C1—C71.465 (2)C11—C121.369 (3)
C2—C31.378 (3)C11—H110.9300
C3—C41.377 (3)C12—C131.374 (3)
C3—H30.9300C13—C141.380 (3)
C4—C51.373 (3)C13—H130.9300
C4—H40.9300C14—H140.9300
C7—N1—N2116.21 (14)N1—C7—H7120.3
C8—N2—N1117.98 (14)C1—C7—H7120.3
C8—N2—H2123.6 (13)O1—C8—N2122.62 (16)
N1—N2—H2118.3 (13)O1—C8—C9120.95 (16)
C6—C1—C2117.03 (17)N2—C8—C9116.41 (14)
C6—C1—C7120.97 (17)C10—C9—C14118.77 (16)
C2—C1—C7122.00 (17)C10—C9—C8123.30 (15)
C3—C2—C1121.92 (19)C14—C9—C8117.92 (15)
C3—C2—Cl1117.90 (16)C11—C10—C9120.28 (17)
C1—C2—Cl1120.15 (14)C11—C10—H10119.9
C4—C3—C2119.4 (2)C9—C10—H10119.9
C4—C3—H3120.3C12—C11—C10119.86 (17)
C2—C3—H3120.3C12—C11—H11120.1
C5—C4—C3120.14 (19)C10—C11—H11120.1
C5—C4—H4119.9C11—C12—C13121.14 (17)
C3—C4—H4119.9C11—C12—Cl2119.47 (15)
C4—C5—C6120.2 (2)C13—C12—Cl2119.39 (15)
C4—C5—H5119.9C12—C13—C14118.83 (18)
C6—C5—H5119.9C12—C13—H13120.6
C5—C6—C1121.34 (19)C14—C13—H13120.6
C5—C6—H6119.3C13—C14—C9121.04 (18)
C1—C6—H6119.3C13—C14—H14119.5
N1—C7—C1119.33 (16)C9—C14—H14119.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.89 (1)2.07 (1)2.9157 (18)160 (2)
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H10Cl2N2O
Mr293.14
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)10.9140 (4), 13.3253 (4), 9.1283 (3)
β (°) 96.165 (2)
V3)1319.87 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.48
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART 1K
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.910, 0.918
No. of measured, independent and
observed [I > 2σ(I)] reflections
7970, 2863, 2099
Rint0.023
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.103, 1.05
No. of reflections2863
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.23

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—H2···O1i0.889 (9)2.065 (11)2.9157 (18)159.8 (18)
Symmetry code: (i) x, y+1/2, z+1/2.
 

Acknowledgements

The Vital Foundation of Ankang University (project No. 2008AKXY012), and the Special Scientific Research Found­ation of the Education Office of Shanxi Province (Project No. 02 J K202) are gratefully acknowledged.

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCao, G.-B. (2009a). Acta Cryst. E65, o2085.  Web of Science CSD CrossRef IUCr Journals
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First citationYang, D.-S. (2007). J. Chem. Crystallogr. 37, 343–348.  Web of Science CSD CrossRef CAS
First citationYang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186.  Web of Science CSD CrossRef IUCr Journals
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