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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 18 November 2008; accepted 19 November 2008; online 26 November 2008)

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[Hu, Z.-Q., Wu, Y., Jia, B., Shi, S.-M., Zhu, X.-D. & Song, F.-H. (2005). Wuji Huaxue Xuebao, 21, 1715-1718.]); Wu et al. (2006[Wu, Y., Cheng, C.-X., Shi, S.-M., Jia, B. & Hu, Z.-Q. (2006). Huazhong Shifan Daxue Xuebao, Ziran Kexueban, 40, 55-57.]); Yehye et al. (2008a[Yehye, W. A., Ariffin, A. & Ng, S. W. (2008a). Acta Cryst. E64, o1452.],b[Yehye, W. A., Ariffin, A. & Ng, S. W. (2008b). Acta Cryst. E64, o961.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10BrClN2O3

  • Mr = 369.60

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.446, Tmax = 0.856

  • 12350 measured reflections

  • 3136 independent reflections

  • 2545 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯O2i 0.83 (1) 1.76 (1) 2.591 (2) 175 (3)
O3—H3o⋯N2 0.84 (1) 1.88 (2) 2.632 (3) 149 (3)
N1—H1n⋯O1 0.87 (1) 1.90 (2) 2.614 (3) 139 (2)
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with atoms shown at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.
N'-(3-Bromo-5-chloro-2-hydroxybenzylidine)-2-hydroxybenzohydrazide top
Crystal data top
C14H10BrClN2O3F(000) = 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 = 3.2–28.2°
b = 6.9319 (1) ŵ = 3.21 mm1
c = 12.9951 (3) ÅT = 100 K
β = 106.461 (1)°Plate, yellow
V = 1368.28 (5) Å30.30 × 0.20 × 0.05 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
3136 independent reflections
Radiation source: fine-focus sealed tube2545 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2020
Tmin = 0.446, Tmax = 0.856k = 98
12350 measured reflectionsl = 1616
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)] = 0.029Hydrogen site location: difmap and geom
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0353P)2 + 1.3959P]
where P = (Fo2 + 2Fc2)/3
3136 reflections(Δ/σ)max = 0.001
202 parametersΔρmax = 0.43 e Å3
3 restraintsΔρmin = 0.41 e Å3
Crystal data top
C14H10BrClN2O3V = 1368.28 (5) Å3
Mr = 369.60Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.8387 (3) ŵ = 3.21 mm1
b = 6.9319 (1) ÅT = 100 K
c = 12.9951 (3) Å0.30 × 0.20 × 0.05 mm
β = 106.461 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer
3136 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2545 reflections with I > 2σ(I)
Tmin = 0.446, Tmax = 0.856Rint = 0.038
12350 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0293 restraints
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.43 e Å3
3136 reflectionsΔρmin = 0.41 e Å3
202 parameters
Special details top

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) top
xyzUiso*/Ueq
Br10.145097 (18)0.43521 (4)0.04463 (2)0.02196 (9)
Cl10.04591 (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) top
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, º) top
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—C3179.7 (2)N2—C8—C9—C106.4 (4)
C6—C1—C2—C30.5 (4)C14—C9—C10—O3179.4 (2)
C1—C2—C3—C40.8 (4)C8—C9—C10—O30.7 (4)
C2—C3—C4—C50.6 (4)C14—C9—C10—C110.5 (4)
C3—C4—C5—C60.1 (4)C8—C9—C10—C11179.2 (2)
O1—C1—C6—C5179.1 (2)O3—C10—C11—C12179.1 (2)
C2—C1—C6—C50.2 (4)C9—C10—C11—C120.9 (4)
O1—C1—C6—C72.6 (4)O3—C10—C11—Br10.5 (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—C7178.0 (2)Br1—C11—C12—C13179.88 (18)
N2—N1—C7—O21.8 (4)C11—C12—C13—C140.1 (4)
N2—N1—C7—C6178.3 (2)C11—C12—C13—Cl1179.70 (19)
C1—C6—C7—O2172.2 (2)C12—C13—C14—C90.5 (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—N1173.8 (2)C8—C9—C14—C13178.6 (2)
N1—N2—C8—C9179.6 (2)
Hydrogen-bond geometry (Å, º) top
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 code: (i) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H10BrClN2O3
Mr369.60
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)15.8387 (3), 6.9319 (1), 12.9951 (3)
β (°) 106.461 (1)
V3)1368.28 (5)
Z4
Radiation typeMo Kα
µ (mm1)3.21
Crystal size (mm)0.30 × 0.20 × 0.05
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.446, 0.856
No. of measured, independent and
observed [I > 2σ(I)] reflections
12350, 3136, 2545
Rint0.038
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.077, 1.02
No. of reflections3136
No. of parameters202
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.41

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
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 code: (i) x, y+3/2, z+1/2.
 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHu, Z.-Q., Wu, Y., Jia, B., Shi, S.-M., Zhu, X.-D. & Song, F.-H. (2005). Wuji Huaxue Xuebao, 21, 1715–1718.  CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar
First citationWu, Y., Cheng, C.-X., Shi, S.-M., Jia, B. & Hu, Z.-Q. (2006). Huazhong Shifan Daxue Xuebao, Ziran Kexueban, 40, 55–57.  Google Scholar
First citationYehye, W. A., Ariffin, A. & Ng, S. W. (2008a). Acta Cryst. E64, o1452.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYehye, W. A., Ariffin, A. & Ng, S. W. (2008b). Acta Cryst. E64, o961.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds