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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2438.
Published online 2008 November 26. doi:  10.1107/S1600536808038634
PMCID: PMC2959983

N′-(3-Bromo-5-chloro-2-hydroxy­benzyl­idine)-2-hydroxy­benzohydrazide

Abstract

In the approximately planar title mol­ecule, C14H10BrClN3O2, the dihedral angle between the aromatic ring planes is 5.79 (12)°. The conformation is stabilized by intra­molecular O—H(...)N and N—H(...)O hydrogen bonds and an inter­molecular O—H(...)O link leads to chains in the crystal propagating in [001].

Related literature

For similar Schiff bases, see: Hu et al. (2005 [triangle]); Wu et al. (2006 [triangle]); Yehye et al. (2008a [triangle],b [triangle]).

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Object name is e-64-o2438-scheme1.jpg

Experimental

Crystal data

  • C14H10BrClN2O3
  • M r = 369.60
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2438-efi1.jpg
  • a = 15.8387 (3) Å
  • b = 6.9319 (1) Å
  • c = 12.9951 (3) Å
  • β = 106.461 (1)°
  • V = 1368.28 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.21 mm−1
  • T = 100 (2) K
  • 0.30 × 0.20 × 0.05 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.446, T max = 0.856
  • 12350 measured reflections
  • 3136 independent reflections
  • 2545 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.077
  • S = 1.02
  • 3136 reflections
  • 202 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038634/hb2857sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038634/hb2857Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

In the approximately planar title molecule, (I), (Fig. 1) the dihedral angle between the aromatic ring planes is 5.79 (12)°. The conformation is stabilised by intramolecular O—H···N and N—H···O hydrogen bonds and an intermolecular O—H···O link leads to chains in the crystal (Table 1).

Experimental

2-Hydroxybenzohydrazide(0.60 g, 4 mmol) and 3-bromo-5-chloro-2-ydroxybenzaldehyde (0.94 g, 4 mmol) were heated in ethanol (30 ml) for 2 h. The solvent was removed by evaporation and the resulting solid was recrystallized from ethanol to yield yellow plates of (I).

Refinement

The carbon-bound H-atoms were placed in calculated positions (C–H = 0.95 Å) and refined as riding with U(H) = 1.2U(C). The oxygen- and nitrogen-bound H-atoms were located in a difference map, and were refined with distance restraints of O–H 0.84±0.01 and N–H 0.88±0.01 Å. Their Uiso values were freely refined.

Figures

Fig. 1.
The molecular structure of (I) with atoms shown at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.

Crystal data

C14H10BrClN2O3F000 = 736
Mr = 369.60Dx = 1.794 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3691 reflections
a = 15.8387 (3) Åθ = 3.2–28.2º
b = 6.9319 (1) ŵ = 3.21 mm1
c = 12.9951 (3) ÅT = 100 (2) K
β = 106.461 (1)ºPlate, yellow
V = 1368.28 (5) Å30.30 × 0.20 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer3136 independent reflections
Radiation source: fine-focus sealed tube2545 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.3º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −20→20
Tmin = 0.446, Tmax = 0.856k = −9→8
12350 measured reflectionsl = −16→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difmap and geom
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077  w = 1/[σ2(Fo2) + (0.0353P)2 + 1.3959P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3136 reflectionsΔρmax = 0.43 e Å3
202 parametersΔρmin = −0.41 e Å3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.145097 (18)0.43521 (4)0.04463 (2)0.02196 (9)
Cl1−0.04591 (4)0.45367 (9)0.33930 (5)0.01932 (14)
O10.48671 (11)0.8436 (3)0.72174 (14)0.0186 (4)
H1O0.495 (2)0.837 (5)0.7879 (9)0.033 (9)*
O20.52114 (12)0.6952 (3)0.42779 (14)0.0224 (4)
O30.28679 (12)0.5844 (3)0.23371 (14)0.0184 (4)
H3O0.3254 (15)0.616 (4)0.2897 (15)0.027 (9)*
N10.42237 (13)0.7471 (3)0.52022 (16)0.0142 (4)
H1N0.4157 (17)0.778 (4)0.5825 (12)0.015 (7)*
N20.35545 (13)0.6804 (3)0.43620 (16)0.0154 (4)
C10.56768 (15)0.8577 (4)0.70555 (19)0.0140 (5)
C20.64075 (16)0.9151 (4)0.7881 (2)0.0163 (5)
H20.63430.94450.85690.020*
C30.72242 (16)0.9295 (4)0.7702 (2)0.0171 (5)
H30.77200.96700.82710.021*
C40.73279 (16)0.8897 (4)0.6701 (2)0.0174 (5)
H40.78900.90100.65810.021*
C50.66035 (16)0.8333 (4)0.5875 (2)0.0158 (5)
H50.66740.80610.51870.019*
C60.57684 (15)0.8157 (3)0.60395 (19)0.0131 (5)
C70.50521 (16)0.7480 (3)0.51062 (19)0.0149 (5)
C80.27901 (16)0.6691 (4)0.4507 (2)0.0154 (5)
H80.27060.70700.51740.018*
C90.20470 (16)0.5978 (3)0.3648 (2)0.0155 (5)
C100.21190 (16)0.5580 (3)0.2611 (2)0.0153 (5)
C110.13777 (17)0.4882 (4)0.1845 (2)0.0162 (5)
C120.05895 (16)0.4549 (3)0.2073 (2)0.0169 (5)
H120.00950.40620.15380.020*
C130.05363 (16)0.4941 (4)0.3096 (2)0.0163 (5)
C140.12487 (17)0.5652 (3)0.3880 (2)0.0171 (5)
H140.11970.59210.45770.020*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.02322 (15)0.02735 (15)0.01301 (13)−0.00167 (11)0.00141 (10)−0.00143 (11)
Cl10.0119 (3)0.0207 (3)0.0259 (3)−0.0026 (2)0.0063 (2)−0.0016 (3)
O10.0127 (9)0.0334 (10)0.0096 (8)−0.0027 (8)0.0032 (7)−0.0009 (8)
O20.0184 (9)0.0369 (11)0.0111 (9)0.0009 (8)0.0027 (7)−0.0044 (8)
O30.0149 (9)0.0247 (10)0.0149 (9)−0.0035 (7)0.0029 (7)−0.0025 (8)
N10.0129 (10)0.0201 (11)0.0079 (10)−0.0002 (8)0.0000 (8)−0.0028 (8)
N20.0148 (10)0.0162 (10)0.0113 (10)0.0002 (8)−0.0027 (8)−0.0009 (8)
C10.0124 (12)0.0151 (12)0.0136 (12)0.0003 (9)0.0020 (9)0.0018 (10)
C20.0162 (12)0.0192 (12)0.0122 (12)−0.0016 (10)0.0018 (10)−0.0003 (10)
C30.0131 (12)0.0181 (12)0.0176 (12)−0.0002 (10)0.0000 (10)0.0005 (11)
C40.0127 (12)0.0188 (13)0.0209 (13)0.0007 (10)0.0052 (10)0.0017 (10)
C50.0167 (12)0.0163 (12)0.0150 (12)0.0017 (10)0.0054 (10)0.0012 (10)
C60.0137 (11)0.0127 (11)0.0113 (11)0.0010 (9)0.0008 (9)0.0021 (9)
C70.0168 (12)0.0151 (11)0.0116 (12)0.0017 (10)0.0018 (10)0.0028 (10)
C80.0170 (12)0.0144 (12)0.0124 (11)0.0013 (10)0.0005 (10)−0.0014 (10)
C90.0140 (12)0.0147 (12)0.0157 (12)0.0005 (9)0.0009 (10)−0.0004 (10)
C100.0144 (12)0.0133 (12)0.0177 (12)0.0022 (9)0.0038 (10)0.0040 (10)
C110.0185 (13)0.0147 (11)0.0132 (12)0.0014 (10)0.0011 (10)0.0004 (10)
C120.0140 (12)0.0152 (12)0.0175 (13)−0.0008 (10)−0.0021 (10)−0.0002 (10)
C130.0126 (12)0.0132 (11)0.0224 (13)0.0007 (9)0.0038 (10)0.0010 (10)
C140.0188 (12)0.0150 (12)0.0166 (12)0.0020 (10)0.0037 (10)0.0003 (10)

Geometric parameters (Å, °)

Br1—C111.890 (3)C3—H30.9500
Cl1—C131.749 (3)C4—C51.387 (4)
O1—C11.361 (3)C4—H40.9500
O1—H1O0.833 (10)C5—C61.404 (3)
O2—C71.229 (3)C5—H50.9500
O3—C101.344 (3)C6—C71.483 (3)
O3—H3O0.836 (10)C8—C91.459 (3)
N1—C71.353 (3)C8—H80.9500
N1—N21.369 (3)C9—C141.399 (4)
N1—H1N0.872 (10)C9—C101.412 (4)
N2—C81.279 (3)C10—C111.393 (3)
C1—C21.395 (3)C11—C121.382 (4)
C1—C61.399 (3)C12—C131.383 (4)
C2—C31.382 (4)C12—H120.9500
C2—H20.9500C13—C141.379 (4)
C3—C41.384 (4)C14—H140.9500
C1—O1—H1O106 (2)O2—C7—N1121.6 (2)
C10—O3—H3O107 (2)O2—C7—C6120.8 (2)
C7—N1—N2118.7 (2)N1—C7—C6117.6 (2)
C7—N1—H1N117.4 (18)N2—C8—C9120.0 (2)
N2—N1—H1N123.5 (18)N2—C8—H8120.0
C8—N2—N1117.0 (2)C9—C8—H8120.0
O1—C1—C2121.0 (2)C14—C9—C10119.8 (2)
O1—C1—C6119.0 (2)C14—C9—C8118.2 (2)
C2—C1—C6120.0 (2)C10—C9—C8122.0 (2)
C3—C2—C1120.2 (2)O3—C10—C11119.1 (2)
C3—C2—H2119.9O3—C10—C9122.8 (2)
C1—C2—H2119.9C11—C10—C9118.0 (2)
C2—C3—C4120.7 (2)C12—C11—C10122.3 (2)
C2—C3—H3119.6C12—C11—Br1118.63 (19)
C4—C3—H3119.6C10—C11—Br1119.05 (19)
C3—C4—C5119.4 (2)C11—C12—C13118.6 (2)
C3—C4—H4120.3C11—C12—H12120.7
C5—C4—H4120.3C13—C12—H12120.7
C4—C5—C6121.0 (2)C14—C13—C12121.3 (2)
C4—C5—H5119.5C14—C13—Cl1119.6 (2)
C6—C5—H5119.5C12—C13—Cl1119.01 (19)
C1—C6—C5118.7 (2)C13—C14—C9119.9 (2)
C1—C6—C7125.3 (2)C13—C14—H14120.0
C5—C6—C7116.0 (2)C9—C14—H14120.0
C7—N1—N2—C8175.3 (2)N2—C8—C9—C14172.3 (2)
O1—C1—C2—C3−179.7 (2)N2—C8—C9—C10−6.4 (4)
C6—C1—C2—C3−0.5 (4)C14—C9—C10—O3−179.4 (2)
C1—C2—C3—C40.8 (4)C8—C9—C10—O3−0.7 (4)
C2—C3—C4—C5−0.6 (4)C14—C9—C10—C110.5 (4)
C3—C4—C5—C6−0.1 (4)C8—C9—C10—C11179.2 (2)
O1—C1—C6—C5179.1 (2)O3—C10—C11—C12179.1 (2)
C2—C1—C6—C5−0.2 (4)C9—C10—C11—C12−0.9 (4)
O1—C1—C6—C7−2.6 (4)O3—C10—C11—Br1−0.5 (3)
C2—C1—C6—C7178.1 (2)C9—C10—C11—Br1179.55 (18)
C4—C5—C6—C10.4 (4)C10—C11—C12—C130.6 (4)
C4—C5—C6—C7−178.0 (2)Br1—C11—C12—C13−179.88 (18)
N2—N1—C7—O21.8 (4)C11—C12—C13—C140.1 (4)
N2—N1—C7—C6−178.3 (2)C11—C12—C13—Cl1179.70 (19)
C1—C6—C7—O2−172.2 (2)C12—C13—C14—C9−0.5 (4)
C5—C6—C7—O26.1 (3)Cl1—C13—C14—C9179.98 (18)
C1—C6—C7—N17.9 (4)C10—C9—C14—C130.1 (4)
C5—C6—C7—N1−173.8 (2)C8—C9—C14—C13−178.6 (2)
N1—N2—C8—C9−179.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.83 (1)1.76 (1)2.591 (2)175 (3)
O3—H3o···N20.84 (1)1.88 (2)2.632 (3)149 (3)
N1—H1n···O10.87 (1)1.90 (2)2.614 (3)139 (2)

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: HB2857).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hu, Z.-Q., Wu, Y., Jia, B., Shi, S.-M., Zhu, X.-D. & Song, F.-H. (2005). Wuji Huaxue Xuebao, 21, 1715–1718.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.
  • Wu, Y., Cheng, C.-X., Shi, S.-M., Jia, B. & Hu, Z.-Q. (2006). Huazhong Shifan Daxue Xuebao, Ziran Kexueban, 40, 55–57.
  • Yehye, W. A., Ariffin, A. & Ng, S. W. (2008a). Acta Cryst. E64, o1452. [PMC free article] [PubMed]
  • Yehye, W. A., Ariffin, A. & Ng, S. W. (2008b). Acta Cryst. E64, o961. [PMC free article] [PubMed]

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