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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1705.
Published online 2009 June 27. doi:  10.1107/S160053680902412X
PMCID: PMC2969211

(E)-3-Bromo-N′-(2-chloro­benzyl­idene)benzohydrazide

Abstract

The title compound, C14H10BrClN2O, was synthesized by the reaction of 2-chloro­benzaldehyde with an equimolar quantity of 3-bromo­benzohydrazide in methanol. The mol­ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.0 (2)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds, forming chains propagating along the c axis.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o1705-scheme1.jpg

Experimental

Crystal data

  • C14H10BrClN2O
  • M r = 337.60
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1705-efi1.jpg
  • a = 13.140 (1) Å
  • b = 12.632 (1) Å
  • c = 8.377 (1) Å
  • β = 98.174 (2)°
  • V = 1376.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.17 mm−1
  • T = 298 K
  • 0.27 × 0.25 × 0.22 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.481, T max = 0.542 (expected range = 0.442–0.498)
  • 8319 measured reflections
  • 2998 independent reflections
  • 2235 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.076
  • S = 1.03
  • 2998 reflections
  • 176 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.52 e Å−3
  • Δρmin = −0.65 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902412X/ci2833sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902412X/ci2833Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

Study on the crystal structures of hydrazone derivatives is a hot topic in structural chemistry. 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), the title new hydrazone compound derived from the reaction of 2-chlorobenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide is reported.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 13.0 (2)°. The molecule displays an E configuration about the C═N 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).

Experimental

The title compound was prepared by refluxing equimolar quantities of 2-chlorobenzaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed by slow evaporation of the solution in air.

Refinement

Atom 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).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The crystal packing of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Crystal data

C14H10BrClN2OF(000) = 672
Mr = 337.60Dx = 1.629 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2981 reflections
a = 13.140 (1) Åθ = 2.2–27.5°
b = 12.632 (1) ŵ = 3.17 mm1
c = 8.377 (1) ÅT = 298 K
β = 98.174 (2)°Block, colourless
V = 1376.3 (2) Å30.27 × 0.25 × 0.22 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2998 independent reflections
Radiation source: fine-focus sealed tube2235 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −16→15
Tmin = 0.481, Tmax = 0.542k = −16→13
8319 measured reflectionsl = −10→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076w = 1/[σ2(Fo2) + (0.0266P)2 + 0.7889P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2998 reflectionsΔρmax = 0.52 e Å3
176 parametersΔρmin = −0.65 e Å3
1 restraintExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0155 (8)

Special details

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)

xyzUiso*/Ueq
Br11.03493 (2)0.63367 (3)0.15480 (4)0.06855 (15)
Cl10.71461 (6)1.15851 (6)0.46918 (11)0.0757 (3)
N10.69113 (14)0.83453 (15)0.6106 (2)0.0358 (4)
N20.74414 (15)0.76627 (15)0.5225 (2)0.0378 (4)
O10.75662 (14)0.64019 (12)0.71573 (18)0.0477 (4)
C10.62315 (16)1.00731 (17)0.6291 (3)0.0342 (5)
C20.62851 (18)1.11440 (19)0.5940 (3)0.0433 (6)
C30.5678 (2)1.1884 (2)0.6563 (3)0.0542 (7)
H30.57321.25960.63100.065*
C40.4996 (2)1.1563 (2)0.7553 (3)0.0572 (7)
H40.45811.20570.79700.069*
C50.4924 (2)1.0510 (2)0.7933 (3)0.0523 (7)
H50.44591.02930.86070.063*
C60.55369 (18)0.9775 (2)0.7319 (3)0.0429 (6)
H60.54870.90660.75960.052*
C70.68317 (17)0.92838 (18)0.5560 (3)0.0367 (5)
H70.71590.94690.46860.044*
C80.77228 (16)0.67075 (17)0.5825 (2)0.0336 (5)
C90.82605 (15)0.60205 (17)0.4763 (2)0.0319 (5)
C100.89265 (16)0.64395 (18)0.3775 (3)0.0359 (5)
H100.90360.71660.37420.043*
C110.94190 (17)0.5767 (2)0.2851 (3)0.0395 (5)
C120.9267 (2)0.4693 (2)0.2864 (3)0.0487 (6)
H120.96030.42490.22250.058*
C130.8606 (2)0.4287 (2)0.3844 (3)0.0498 (6)
H130.84900.35610.38590.060*
C140.81123 (18)0.49435 (18)0.4804 (3)0.0411 (5)
H140.76790.46580.54790.049*
H20.749 (2)0.784 (2)0.4206 (17)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0647 (2)0.0867 (3)0.0630 (2)0.00759 (16)0.03940 (15)0.00891 (15)
Cl10.0682 (5)0.0610 (5)0.1056 (6)0.0046 (4)0.0393 (4)0.0307 (4)
N10.0373 (10)0.0395 (11)0.0326 (9)0.0065 (8)0.0121 (8)−0.0033 (8)
N20.0477 (11)0.0400 (11)0.0292 (9)0.0105 (9)0.0168 (8)0.0004 (8)
O10.0696 (12)0.0445 (10)0.0339 (8)0.0059 (8)0.0236 (8)0.0038 (7)
C10.0307 (11)0.0393 (12)0.0322 (11)0.0033 (9)0.0031 (9)−0.0017 (9)
C20.0375 (12)0.0439 (14)0.0487 (14)0.0022 (10)0.0063 (10)0.0019 (10)
C30.0551 (15)0.0383 (14)0.0686 (18)0.0081 (12)0.0063 (14)−0.0028 (12)
C40.0551 (16)0.0562 (17)0.0609 (17)0.0170 (13)0.0102 (14)−0.0140 (13)
C50.0474 (14)0.0642 (18)0.0484 (15)0.0073 (13)0.0175 (12)−0.0042 (13)
C60.0429 (13)0.0435 (14)0.0443 (13)0.0035 (11)0.0127 (11)−0.0016 (11)
C70.0383 (12)0.0423 (14)0.0314 (11)0.0033 (10)0.0114 (9)0.0015 (10)
C80.0352 (11)0.0369 (12)0.0300 (11)0.0002 (9)0.0096 (9)−0.0022 (9)
C90.0297 (11)0.0382 (12)0.0280 (10)0.0051 (9)0.0049 (8)0.0002 (9)
C100.0369 (12)0.0392 (12)0.0329 (11)0.0027 (10)0.0088 (9)−0.0006 (9)
C110.0341 (11)0.0526 (15)0.0336 (11)0.0064 (10)0.0112 (9)0.0018 (10)
C120.0508 (14)0.0518 (16)0.0450 (14)0.0149 (12)0.0119 (11)−0.0089 (12)
C130.0573 (15)0.0353 (13)0.0576 (15)0.0054 (12)0.0114 (12)−0.0040 (11)
C140.0410 (13)0.0413 (14)0.0427 (13)0.0021 (10)0.0120 (10)0.0025 (10)

Geometric parameters (Å, °)

Br1—C111.892 (2)C5—C61.376 (3)
Cl1—C21.738 (2)C5—H50.93
N1—C71.270 (3)C6—H60.93
N1—N21.386 (2)C7—H70.93
N2—C81.339 (3)C8—C91.491 (3)
N2—H20.893 (10)C9—C141.376 (3)
O1—C81.226 (2)C9—C101.392 (3)
C1—C21.388 (3)C10—C111.372 (3)
C1—C61.393 (3)C10—H100.93
C1—C71.459 (3)C11—C121.372 (4)
C2—C31.378 (3)C12—C131.376 (4)
C3—C41.366 (4)C12—H120.93
C3—H30.93C13—C141.379 (3)
C4—C51.374 (4)C13—H130.93
C4—H40.93C14—H140.93
C7—N1—N2114.24 (17)N1—C7—H7119.7
C8—N2—N1119.58 (17)C1—C7—H7119.7
C8—N2—H2122 (2)O1—C8—N2123.53 (19)
N1—N2—H2118 (2)O1—C8—C9121.02 (19)
C2—C1—C6116.9 (2)N2—C8—C9115.44 (18)
C2—C1—C7122.0 (2)C14—C9—C10119.6 (2)
C6—C1—C7121.1 (2)C14—C9—C8118.69 (19)
C3—C2—C1122.1 (2)C10—C9—C8121.7 (2)
C3—C2—Cl1118.1 (2)C11—C10—C9119.2 (2)
C1—C2—Cl1119.79 (18)C11—C10—H10120.4
C4—C3—C2119.6 (2)C9—C10—H10120.4
C4—C3—H3120.2C10—C11—C12121.8 (2)
C2—C3—H3120.2C10—C11—Br1119.05 (18)
C3—C4—C5120.1 (2)C12—C11—Br1119.17 (17)
C3—C4—H4120.0C11—C12—C13118.6 (2)
C5—C4—H4120.0C11—C12—H12120.7
C4—C5—C6120.2 (2)C13—C12—H12120.7
C4—C5—H5119.9C12—C13—C14120.8 (2)
C6—C5—H5119.9C12—C13—H13119.6
C5—C6—C1121.3 (2)C14—C13—H13119.6
C5—C6—H6119.4C9—C14—C13120.0 (2)
C1—C6—H6119.4C9—C14—H14120.0
N1—C7—C1120.54 (19)C13—C14—H14120.0

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.89 (1)1.98 (1)2.854 (2)165 (3)

Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2833).

References

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