PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o508.
Published online 2009 February 11. doi:  10.1107/S1600536809002165
PMCID: PMC2968684

(E)-4-Bromo-N′-(2-nitro­benzyl­idene)benzohydrazide

Abstract

The title compound, C14H10BrN3O3, was obtained by a condensation reaction between 2-nitro­benzaldehyde and 4-bromo­benzohydrazide. The dihedral angle between the two benzene rings is 4.1 (2)°. The mol­ecule displays an E configuration about the C=N bond. In the crystal, mol­ecules are linked into a chain along [100] by inter­molecular N—H(...)O hydrogen bonds.

Related literature

For the biological properties of Schiff base and hydrazone compounds, see: Kucukguzel et al. (2006 [triangle]); Khattab et al. (2005 [triangle]); Karthikeyan et al. (2006 [triangle]); Okabe et al. (1993 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For related structures, see: Shan et al. (2008 [triangle]); Fun et al. (2008 [triangle]); Ma et al. (2008 [triangle]); Diao et al. (2008a [triangle],b [triangle]); Ejsmont et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o508-scheme1.jpg

Experimental

Crystal data

  • C14H10BrN3O3
  • M r = 348.16
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o508-efi1.jpg
  • a = 4.8718 (17) Å
  • b = 6.842 (2) Å
  • c = 10.709 (4) Å
  • α = 98.014 (5)°
  • β = 93.258 (6)°
  • γ = 97.413 (5)°
  • V = 349.5 (2) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 2.95 mm−1
  • T = 298 (2) K
  • 0.20 × 0.18 × 0.17 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.590, T max = 0.634
  • 2347 measured reflections
  • 1998 independent reflections
  • 1584 reflections with I > 2σ(I)
  • R int = 0.013

Refinement

  • R[F 2 > 2σ(F 2)] = 0.027
  • wR(F 2) = 0.064
  • S = 0.95
  • 1998 reflections
  • 193 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.23 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 235 Friedel pairs
  • Flack parameter: 0.021 (8)

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/S1600536809002165/ci2760sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002165/ci2760Isup2.hkl

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

Acknowledgments

This project was supported by Jilin University.

supplementary crystallographic information

Comment

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab et al., 2005; Karthikeyan et al., 2006; Okabe et al., 1993). Recently, a large number of hydrazone derivatives have been prepared and structurally characterized (Shan et al., 2008; Fun et al., 2008; Ma et al., 2008; Diao et al., 2008a,b; Ejsmont et al., 2008). As part of the ongoing study, we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the two benzene rings is 4.1 (2)°. The molecule of the compound displays an E configuration about the C═N bond. The bond values are typical (Allen et al., 1987). The molecules are linked into a chain along the [100] by intermolecular N—H···O hydrogen bonds.

Experimental

2-Nitrobenzaldehyde (1.0 mmol, 151.1 mg) was dissolved in methanol (50 ml) and then 4-bromobenzohydrazide (1.0 mmol, 215.0 mg) was added slowly into the solution, and the mixture was kept at reflux with continuous stirring for 1 h. After the solution had cooled to room temperature colourless crystals appeared. The crystals were filtered and washed with methanol for three times. Recrystallization from an absolute methanol yielded block-shaped single crystals of the title compound.

Refinement

The amide H atom was located in a difference map and its positional parameters were refined. All other H atoms were placed in calculated positions (C-H = 0.93 Å) and refined using a riding model. The Uiso(H) values were set at 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title compound with 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C14H10BrN3O3Z = 1
Mr = 348.16F(000) = 174
Triclinic, P1Dx = 1.654 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8718 (17) ÅCell parameters from 1163 reflections
b = 6.842 (2) Åθ = 2.8–26.3°
c = 10.709 (4) ŵ = 2.95 mm1
α = 98.014 (5)°T = 298 K
β = 93.258 (6)°Block, colourless
γ = 97.413 (5)°0.20 × 0.18 × 0.17 mm
V = 349.5 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer1998 independent reflections
Radiation source: fine-focus sealed tube1584 reflections with I > 2σ(I)
graphiteRint = 0.013
ω scansθmax = 30.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −6→6
Tmin = 0.590, Tmax = 0.634k = −8→8
2347 measured reflectionsl = −11→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064w = 1/[σ2(Fo2) + (0.0058P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
1998 reflectionsΔρmax = 0.22 e Å3
193 parametersΔρmin = −0.23 e Å3
3 restraintsAbsolute structure: Flack (1983), 235 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.021 (8)

Special details

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)

xyzUiso*/Ueq
Br10.28524 (6)−0.18204 (5)−0.03061 (4)0.08281 (18)
O10.9938 (4)0.7003 (4)0.2644 (2)0.0599 (6)
O20.1064 (8)1.2188 (6)0.7780 (3)0.0860 (11)
O30.2286 (10)0.9674 (5)0.6631 (3)0.1064 (15)
N10.5685 (5)0.7559 (4)0.3185 (2)0.0399 (5)
H10.394 (9)0.725 (7)0.293 (4)0.048*
N20.6709 (5)0.9301 (4)0.3980 (2)0.0405 (5)
N30.2485 (7)1.1447 (5)0.6997 (3)0.0584 (8)
C10.6174 (7)0.4513 (5)0.1848 (3)0.0385 (7)
C20.7401 (7)0.3754 (5)0.0775 (3)0.0506 (8)
H20.89100.45050.04950.061*
C30.6386 (8)0.1890 (6)0.0126 (3)0.0564 (9)
H30.71800.1400−0.06020.068*
C40.4217 (8)0.0767 (5)0.0555 (3)0.0504 (8)
C50.2932 (7)0.1486 (5)0.1614 (3)0.0447 (7)
H50.14290.07220.18890.054*
C60.3932 (6)0.3357 (5)0.2250 (3)0.0420 (7)
H60.30900.38550.29620.050*
C70.7440 (6)0.6473 (4)0.2577 (3)0.0404 (6)
C80.4917 (6)1.0171 (4)0.4562 (3)0.0384 (6)
H80.30610.96090.44790.046*
C90.5831 (6)1.2100 (4)0.5376 (3)0.0393 (6)
C100.4633 (7)1.2766 (5)0.6481 (3)0.0433 (7)
C110.5462 (8)1.4635 (6)0.7158 (3)0.0607 (9)
H110.46341.50290.78960.073*
C120.7486 (9)1.5906 (6)0.6752 (4)0.0660 (10)
H120.80151.71780.71990.079*
C130.8755 (8)1.5290 (5)0.5668 (3)0.0550 (9)
H131.01721.61390.53970.066*
C140.7919 (8)1.3419 (6)0.4990 (3)0.0489 (9)
H140.87721.30310.42580.059*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1255 (4)0.04369 (19)0.0679 (2)−0.00267 (18)0.00284 (18)−0.01585 (13)
O10.0231 (11)0.0608 (15)0.0872 (15)−0.0003 (10)0.0026 (10)−0.0128 (12)
O20.082 (2)0.113 (3)0.074 (2)0.030 (2)0.0420 (17)0.0233 (19)
O30.149 (4)0.068 (3)0.087 (2)−0.047 (2)0.049 (2)−0.0006 (17)
N10.0237 (12)0.0358 (13)0.0545 (13)−0.0004 (10)−0.0015 (10)−0.0072 (11)
N20.0343 (13)0.0331 (12)0.0494 (12)−0.0022 (10)−0.0040 (10)−0.0015 (10)
N30.057 (2)0.068 (2)0.0476 (14)−0.0014 (16)0.0036 (14)0.0092 (14)
C10.0303 (16)0.0361 (15)0.0469 (15)0.0039 (13)−0.0061 (13)0.0027 (12)
C20.0450 (19)0.050 (2)0.0551 (17)0.0058 (15)0.0104 (14)0.0015 (15)
C30.067 (2)0.057 (2)0.0417 (15)0.0094 (18)0.0084 (15)−0.0075 (14)
C40.062 (2)0.0360 (16)0.0488 (16)0.0072 (15)−0.0087 (15)−0.0032 (13)
C50.0430 (18)0.0365 (16)0.0515 (16)−0.0015 (13)0.0030 (14)0.0024 (13)
C60.0379 (17)0.0418 (17)0.0438 (15)0.0048 (13)0.0031 (13)−0.0008 (13)
C70.0318 (16)0.0389 (16)0.0484 (14)0.0018 (12)−0.0009 (12)0.0038 (12)
C80.0322 (15)0.0356 (15)0.0435 (14)−0.0016 (13)0.0004 (12)−0.0006 (12)
C90.0385 (16)0.0325 (15)0.0444 (14)−0.0001 (12)−0.0029 (12)0.0039 (12)
C100.0401 (17)0.0418 (16)0.0464 (14)0.0022 (13)0.0033 (13)0.0042 (12)
C110.070 (2)0.053 (2)0.0542 (17)0.0114 (19)0.0013 (17)−0.0095 (15)
C120.079 (3)0.0351 (17)0.075 (2)−0.0046 (18)−0.004 (2)−0.0064 (16)
C130.058 (2)0.0404 (19)0.0614 (19)−0.0124 (15)0.0002 (17)0.0091 (15)
C140.0495 (18)0.041 (2)0.051 (2)−0.0091 (15)0.0001 (17)0.0075 (18)

Geometric parameters (Å, °)

Br1—C41.897 (3)C4—C51.387 (5)
O1—C71.219 (4)C5—C61.377 (4)
O2—N31.216 (5)C5—H50.93
O3—N31.211 (5)C6—H60.93
N1—C71.341 (4)C8—C91.478 (4)
N1—N21.382 (3)C8—H80.93
N1—H10.87 (4)C9—C141.391 (5)
N2—C81.264 (4)C9—C101.395 (4)
N3—C101.474 (5)C10—C111.378 (4)
C1—C61.389 (5)C11—C121.360 (6)
C1—C21.393 (5)C11—H110.93
C1—C71.493 (4)C12—C131.386 (6)
C2—C31.380 (5)C12—H120.93
C2—H20.93C13—C141.380 (5)
C3—C41.364 (5)C13—H130.93
C3—H30.93C14—H140.93
C7—N1—N2119.9 (2)O1—C7—N1122.7 (3)
C7—N1—H1116 (3)O1—C7—C1121.2 (3)
N2—N1—H1123 (3)N1—C7—C1116.0 (2)
C8—N2—N1115.5 (2)N2—C8—C9118.6 (3)
O3—N3—O2123.8 (4)N2—C8—H8120.7
O3—N3—C10117.7 (3)C9—C8—H8120.7
O2—N3—C10118.5 (4)C14—C9—C10116.6 (3)
C6—C1—C2118.7 (3)C14—C9—C8118.6 (3)
C6—C1—C7122.3 (3)C10—C9—C8124.7 (3)
C2—C1—C7118.8 (3)C11—C10—C9121.9 (3)
C3—C2—C1120.2 (3)C11—C10—N3117.4 (3)
C3—C2—H2119.9C9—C10—N3120.7 (3)
C1—C2—H2119.9C12—C11—C10120.3 (3)
C4—C3—C2119.9 (3)C12—C11—H11119.8
C4—C3—H3120.1C10—C11—H11119.8
C2—C3—H3120.1C11—C12—C13119.5 (3)
C3—C4—C5121.3 (3)C11—C12—H12120.3
C3—C4—Br1120.4 (3)C13—C12—H12120.3
C5—C4—Br1118.3 (3)C14—C13—C12120.1 (3)
C6—C5—C4118.6 (3)C14—C13—H13119.9
C6—C5—H5120.7C12—C13—H13119.9
C4—C5—H5120.7C13—C14—C9121.5 (3)
C5—C6—C1121.3 (3)C13—C14—H14119.2
C5—C6—H6119.4C9—C14—H14119.2
C1—C6—H6119.4
C7—N1—N2—C8−176.5 (3)N2—C8—C9—C1436.5 (4)
C6—C1—C2—C30.3 (5)N2—C8—C9—C10−147.7 (3)
C7—C1—C2—C3175.9 (3)C14—C9—C10—C110.1 (4)
C1—C2—C3—C4−1.6 (5)C8—C9—C10—C11−175.8 (3)
C2—C3—C4—C52.2 (5)C14—C9—C10—N3−177.4 (3)
C2—C3—C4—Br1−178.6 (3)C8—C9—C10—N36.6 (4)
C3—C4—C5—C6−1.4 (5)O3—N3—C10—C11−160.0 (4)
Br1—C4—C5—C6179.4 (2)O2—N3—C10—C1118.4 (5)
C4—C5—C6—C10.1 (4)O3—N3—C10—C917.7 (5)
C2—C1—C6—C50.4 (4)O2—N3—C10—C9−163.9 (3)
C7—C1—C6—C5−175.0 (3)C9—C10—C11—C120.6 (5)
N2—N1—C7—O1−3.6 (4)N3—C10—C11—C12178.3 (4)
N2—N1—C7—C1173.8 (2)C10—C11—C12—C13−1.5 (6)
C6—C1—C7—O1143.2 (3)C11—C12—C13—C141.6 (6)
C2—C1—C7—O1−32.3 (4)C12—C13—C14—C9−0.8 (6)
C6—C1—C7—N1−34.3 (4)C10—C9—C14—C130.0 (5)
C2—C1—C7—N1150.3 (3)C8—C9—C14—C13176.1 (3)
N1—N2—C8—C9−176.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.900 (11)1.909 (19)2.791 (3)166 (6)

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2760).

References

  • 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.
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Diao, Y.-P., Huang, S.-S., Zhang, J.-K. & Kang, T.-G. (2008a). Acta Cryst. E64, o470. [PMC free article] [PubMed]
  • Diao, Y.-P., Zhen, Y.-H., Han, X. & Deng, S. (2008b). Acta Cryst. E64, o101. [PMC free article] [PubMed]
  • Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128. [PMC free article] [PubMed]
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Fun, H.-K., Sujith, K. V., Patil, P. S., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1961–o1962. [PMC free article] [PubMed]
  • Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem.14, 7482–7489. [PubMed]
  • Khattab, S. N. (2005). Molecules, 10, 1218–1228. [PubMed]
  • Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahi, F. & Gulluce, M. (2006). Eur. J. Med. Chem.41, 353–359. [PubMed]
  • Ma, H.-B., Huang, S.-S. & Diao, Y.-P. (2008). Acta Cryst. E64, o210. [PMC free article] [PubMed]
  • Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680.
  • Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008). Acta Cryst. E64, o1363. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography