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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o751.
Published online 2010 March 6. doi:  10.1107/S160053681000752X
PMCID: PMC2983862

N′-(5-Bromo-2-hydroxy­benzyl­idene)-4-chloro­benzohydrazide

Abstract

The title Schiff base, C14H10BrClN2O2, exists in a trans configuration with respect to the C=N bond and the dihedral angle between the two benzene rings is 0.8 (2)°. There is an intra­molecular O—H(...)N hydrogen bond in the mol­ecule, which generates an S(6) loop. In the crystal, inter­molecular N—H(...)O hydrogen bonds link adjacent mol­ecules into extended chains propagating along the c-axis direction.

Related literature

For background to the biological properties of Schiff bases, see: Ritter et al. (2009 [triangle]); Bagihalli et al. (2008 [triangle]). For related structures, see: Fun et al. (2008 [triangle]); Shafiq et al. (2009 [triangle]); Goh et al. (2010 [triangle]). Zhou et al. (2009 [triangle]); Zhou & Yang (2009 [triangle], 2010a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o751-scheme1.jpg

Experimental

Crystal data

  • C14H10BrClN2O2
  • M r = 353.60
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o751-efi1.jpg
  • a = 5.893 (2) Å
  • b = 31.708 (11) Å
  • c = 7.437 (3) Å
  • β = 92.017 (8)°
  • V = 1388.8 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.15 mm−1
  • T = 298 K
  • 0.17 × 0.15 × 0.15 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.616, T max = 0.649
  • 7670 measured reflections
  • 2661 independent reflections
  • 1555 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.119
  • S = 1.02
  • 2661 reflections
  • 185 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.51 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/S160053681000752X/hb5343sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000752X/hb5343Isup2.hkl

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

Acknowledgments

The authors acknowledge support of this project by Hunan Provincial Natural Science Foundation of China Scientific Research (09JJ6022) and the Fund of Hunan Provincial Education Department (08B031), People’s Republic of China.

supplementary crystallographic information

Comment

Some Schiff bases possess biological properties, such as antibacterial, antimicrobial, and antitumor activities (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). As a continuation of these studies, in this paper, the crystal structure of the title Schiff base, (I), derived from the condensing of 5-bromo-2-hydroxybenzaldehyde with 4-chlorobenzohydrazide in methanol is reported.

In the title compound, Fig. 1, all the bond lengths are comparable with those observed in other similar compounds (Zhou et al., 2009; Zhou & Yang, 2009; Zhou & Yang, 2010a,b). The molecule exists in a trans configuration with respect to the acyclic C═N bond. There is an intramolecular O—H···N hydrogen bond in the molecule (Table 1). The dihedral angle between the two benzene rings is 0.8 (2)°.

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

Experimental

5-Bromo-2-hydroxybenzaldehyde (1.0 mmol, 201 mg) and 4-chlorobenzohydrazide (1.0 mmol, 170 mg) were dissolved in a methanol solution (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 blocks of (I).

Refinement

H2 attached to N2 was located in a difference map and refined with N—H distance restrained to 0.90 (1)Å. The remaining H atoms were positioned geometrically, with C—H distances of 0.93 Å, O—H distance of 0.82 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I), with ellipsoids drawn at the 30% probability level.
Fig. 2.
The packing of (I), viewed along the a axis. Hydrogen bonds are drawn as dashed lines.

Crystal data

C14H10BrClN2O2F(000) = 704
Mr = 353.60Dx = 1.691 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1461 reflections
a = 5.893 (2) Åθ = 2.5–24.5°
b = 31.708 (11) ŵ = 3.15 mm1
c = 7.437 (3) ÅT = 298 K
β = 92.017 (8)°Block, colourless
V = 1388.8 (9) Å30.17 × 0.15 × 0.15 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer2661 independent reflections
Radiation source: fine-focus sealed tube1555 reflections with I > 2σ(I)
graphiteRint = 0.043
ω scansθmax = 25.9°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.616, Tmax = 0.649k = −38→36
7670 measured reflectionsl = −9→5

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
2661 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.58 e Å3
1 restraintΔρmin = −0.51 e Å3

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
Br10.22343 (9)0.007519 (14)0.69748 (8)0.0934 (3)
Cl1−0.31634 (18)0.42871 (3)0.73651 (14)0.0726 (4)
N10.3457 (5)0.20659 (9)0.8247 (3)0.0456 (7)
N20.2126 (5)0.24185 (9)0.7948 (4)0.0508 (8)
O10.7208 (4)0.16526 (8)0.9180 (4)0.0621 (7)
H10.64220.18630.89990.093*
O20.4098 (4)0.27888 (7)1.0046 (3)0.0604 (7)
C10.3853 (6)0.13282 (10)0.7884 (4)0.0418 (8)
C20.6036 (6)0.13063 (12)0.8651 (4)0.0479 (9)
C30.7070 (6)0.09163 (14)0.8872 (5)0.0617 (11)
H30.85390.09020.93690.074*
C40.5988 (7)0.05541 (13)0.8381 (5)0.0665 (11)
H40.67020.02950.85530.080*
C50.3815 (7)0.05740 (11)0.7622 (5)0.0561 (10)
C60.2773 (6)0.09556 (11)0.7367 (4)0.0485 (9)
H60.13200.09660.68400.058*
C70.2645 (6)0.17218 (11)0.7635 (4)0.0446 (9)
H70.12470.17230.70150.054*
C80.2553 (6)0.27691 (10)0.8913 (5)0.0430 (8)
C90.1038 (5)0.31345 (10)0.8524 (4)0.0385 (8)
C10−0.1114 (6)0.30975 (11)0.7758 (4)0.0470 (9)
H10−0.17000.28320.74910.056*
C11−0.2404 (6)0.34505 (12)0.7387 (5)0.0506 (9)
H11−0.38500.34250.68560.061*
C12−0.1537 (6)0.38413 (11)0.7806 (4)0.0471 (9)
C130.0603 (6)0.38863 (11)0.8575 (4)0.0511 (9)
H130.11840.41530.88380.061*
C140.1861 (6)0.35333 (11)0.8947 (4)0.0465 (9)
H140.32970.35610.94950.056*
H20.107 (5)0.2405 (12)0.705 (4)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1054 (5)0.0446 (3)0.1297 (5)−0.0038 (2)−0.0018 (3)0.0039 (3)
Cl10.0765 (8)0.0562 (7)0.0844 (8)0.0210 (5)−0.0079 (6)−0.0056 (5)
N10.0462 (18)0.0458 (18)0.0441 (17)0.0073 (14)−0.0094 (13)−0.0009 (13)
N20.055 (2)0.0462 (19)0.050 (2)0.0044 (15)−0.0177 (14)−0.0068 (15)
O10.0459 (15)0.0723 (18)0.0670 (18)0.0040 (13)−0.0124 (13)−0.0054 (15)
O20.0676 (17)0.0470 (15)0.0639 (17)−0.0021 (13)−0.0335 (14)0.0001 (12)
C10.043 (2)0.046 (2)0.037 (2)0.0041 (16)0.0006 (15)0.0014 (15)
C20.046 (2)0.057 (2)0.040 (2)0.0024 (18)0.0003 (17)−0.0009 (17)
C30.044 (2)0.079 (3)0.062 (3)0.019 (2)−0.0053 (18)0.008 (2)
C40.068 (3)0.060 (3)0.071 (3)0.024 (2)0.003 (2)0.008 (2)
C50.065 (3)0.047 (2)0.057 (2)0.0047 (19)0.006 (2)0.0083 (17)
C60.048 (2)0.045 (2)0.052 (2)0.0037 (16)−0.0027 (17)0.0042 (16)
C70.043 (2)0.048 (2)0.042 (2)0.0044 (17)−0.0053 (16)0.0019 (16)
C80.041 (2)0.043 (2)0.045 (2)−0.0061 (15)−0.0073 (17)0.0019 (16)
C90.042 (2)0.0411 (19)0.0325 (18)−0.0023 (15)−0.0044 (15)−0.0008 (15)
C100.051 (2)0.042 (2)0.048 (2)−0.0024 (16)−0.0004 (17)−0.0065 (16)
C110.048 (2)0.053 (3)0.051 (2)0.0031 (18)−0.0027 (17)−0.0043 (17)
C120.056 (2)0.045 (2)0.041 (2)0.0075 (17)0.0085 (17)−0.0042 (16)
C130.060 (3)0.041 (2)0.052 (2)−0.0033 (18)0.0023 (18)−0.0062 (17)
C140.045 (2)0.050 (2)0.045 (2)−0.0046 (17)−0.0068 (16)−0.0041 (16)

Geometric parameters (Å, °)

Br1—C51.889 (4)C4—H40.9300
Cl1—C121.733 (4)C5—C61.367 (5)
N1—C71.269 (4)C6—H60.9300
N1—N21.379 (4)C7—H70.9300
N2—C81.342 (4)C8—C91.485 (4)
N2—H20.898 (10)C9—C101.377 (4)
O1—C21.349 (4)C9—C141.387 (4)
O1—H10.8200C10—C111.376 (5)
O2—C81.220 (4)C10—H100.9300
C1—C61.390 (5)C11—C121.372 (5)
C1—C21.391 (5)C11—H110.9300
C1—C71.445 (5)C12—C131.373 (5)
C2—C31.386 (5)C13—C141.366 (5)
C3—C41.358 (5)C13—H130.9300
C3—H30.9300C14—H140.9300
C4—C51.383 (5)
C7—N1—N2115.7 (3)N1—C7—H7119.4
C8—N2—N1119.4 (3)C1—C7—H7119.4
C8—N2—H2123 (3)O2—C8—N2122.2 (3)
N1—N2—H2117 (3)O2—C8—C9121.6 (3)
C2—O1—H1109.5N2—C8—C9116.2 (3)
C6—C1—C2118.6 (3)C10—C9—C14118.8 (3)
C6—C1—C7118.7 (3)C10—C9—C8123.6 (3)
C2—C1—C7122.7 (3)C14—C9—C8117.7 (3)
O1—C2—C3118.3 (3)C11—C10—C9120.6 (3)
O1—C2—C1122.4 (3)C11—C10—H10119.7
C3—C2—C1119.3 (3)C9—C10—H10119.7
C4—C3—C2121.5 (4)C12—C11—C10119.3 (3)
C4—C3—H3119.2C12—C11—H11120.3
C2—C3—H3119.2C10—C11—H11120.3
C3—C4—C5119.4 (4)C11—C12—C13121.2 (3)
C3—C4—H4120.3C11—C12—Cl1119.6 (3)
C5—C4—H4120.3C13—C12—Cl1119.2 (3)
C6—C5—C4120.1 (4)C14—C13—C12118.9 (3)
C6—C5—Br1119.4 (3)C14—C13—H13120.5
C4—C5—Br1120.5 (3)C12—C13—H13120.5
C5—C6—C1121.0 (3)C13—C14—C9121.2 (3)
C5—C6—H6119.5C13—C14—H14119.4
C1—C6—H6119.5C9—C14—H14119.4
N1—C7—C1121.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.932.642 (4)145
N2—H2···O2i0.90 (1)1.96 (2)2.829 (3)163 (4)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5343).

References

  • Bagihalli, G. B., Avaji, P. G., Patil, S. A. & Badami, P. S. (2008). Eur. J. Med. Chem.43, 2639–2649. [PubMed]
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fun, H.-K., Chantrapromma, S., Jana, S., Hazra, A. & Goswami, S. (2008). Acta Cryst. E64, o175–o176. [PMC free article] [PubMed]
  • Goh, J. H., Fun, H.-K., Vinayaka, A. C. & Kalluraya, B. (2010). Acta Cryst. E66, o24. [PMC free article] [PubMed]
  • Ritter, E., Przybylski, P., Brzezinski, B. & Bartl, F. (2009). Curr. Org. Chem.13, 241–249.
  • Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2501. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhou, C.-S., Hou, H.-Y. & Yang, T. (2009). Z. Kristallogr. New Cryst. Struct.224, 37–38.
  • Zhou, C.-S. & Yang, T. (2009). Z. Kristallogr. New Cryst. Struct.224, 39–40.
  • Zhou, C.-S. & Yang, T. (2010a). Acta Cryst. E66, o290. [PMC free article] [PubMed]
  • Zhou, C.-S. & Yang, T. (2010b). Acta Cryst. E66, o365. [PMC free article] [PubMed]

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