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Acta Cryst. (2010). E66, o2045    [ doi:10.1107/S1600536810027856 ]

(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate

S. M. Saharin, H. Khaledi and H. Mohd Ali

Abstract top

The Schiff base molecule in the title compound, C14H11BrN2O4·H2O, is almost planar with an r.m.s. deviation for the non-H atoms of 0.16 Å. In the crystal structure, the Schiff base molecules and the water molecules are linked together by intermolecular N-H...O and O-H...O hydrogen bonds, leading to layers parallel to the bc plane. An intramolecular O-H...N hydrogen bond involving the imine N atom and a hydroxy substituent is also observed.

Comment top

The molecular structure of the title compound is shown in Fig. 1, and the crystal structure in Fig. 2. The present study shows that Br and Cl analogues (Deng et al., 2009) are isotypic crystals.

Related literature top

For the isotypic Cl analogue C14H11ClN2O4.H2O, see: Deng et al. (2009).

Experimental top

An ethanolic solution (15 ml) of 3,5-dihydroxybenzohydrazide (0.67 g, 4 mmol) and 5-bromosalicylaldehyde (0.8 g, 4 mmol) was refluxed for 2 h. The solution was then cooled and the solid product formed was filtered off, washed with cold ethanol, and dried over silica gel. Crystals of the title compound were obtained by slow evaporation of a DMSO solution at room temperature.

Refinement top

The carbon-bound H atoms were placed in calculated positions (C—H fixed to 0.93 Å) and treated as riding on their parent carbon atoms with Uiso(H) set to 1.2 Ueq(carrier C). The nitrogen- and oxygen-bound H atoms were located in a difference map and refined as free atoms, with N—H and O—H distances restrained to 0.86 (2) and 0.82 (2) Å, respectively.

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: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the title compound at 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Packing view looking down the crystallographic b unit cell edge.
(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate top
Crystal data top
C14H11BrN2O4·H2OF(000) = 744
Mr = 369.17Dx = 1.721 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3109 reflections
a = 13.5685 (3) Åθ = 3.0–26.1°
b = 8.0532 (2) ŵ = 2.91 mm−1
c = 13.2447 (2) ÅT = 296 K
β = 100.186 (1)°Plate, yellow
V = 1424.44 (5) Å30.58 × 0.33 × 0.06 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		2579 independent reflections
Radiation source: fine-focus sealed tube2183 reflections with I > 2σ(I)
graphiteRint = 0.034
φ and ω scansθmax = 25.3°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→16
Tmin = 0.283, Tmax = 0.845k = −9→9
9148 measured reflectionsl = −15→15
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0328P)2 + 0.7124P]
where P = (Fo2 + 2Fc2)/3
2579 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.45 e Å−3
6 restraintsΔρmin = −0.56 e Å−3
0 constraints
Crystal data top
C14H11BrN2O4·H2OV = 1424.44 (5) Å3
Mr = 369.17Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.5685 (3) ŵ = 2.91 mm−1
b = 8.0532 (2) ÅT = 296 K
c = 13.2447 (2) Å0.58 × 0.33 × 0.06 mm
β = 100.186 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		2579 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2183 reflections with I > 2σ(I)
Tmin = 0.283, Tmax = 0.845Rint = 0.034
9148 measured reflectionsθmax = 25.3°
Refinement top
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077Δρmax = 0.45 e Å−3
S = 1.04Δρmin = −0.56 e Å−3
2579 reflectionsAbsolute structure: ?
217 parametersFlack parameter: ?
6 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.54976 (2)0.19522 (4)0.67677 (2)0.05405 (13)
O10.25489 (15)0.4914 (3)0.33122 (13)0.0448 (5)
H10.210 (2)0.542 (4)0.351 (2)0.067*
O8−0.01522 (14)0.6853 (2)0.34596 (12)0.0375 (4)
O11−0.18429 (14)0.9113 (2)0.71231 (12)0.0378 (4)
H11−0.1355 (18)0.868 (4)0.749 (2)0.057*
O13−0.29944 (14)1.0800 (2)0.37286 (13)0.0440 (5)
H13−0.285 (3)1.075 (4)0.3181 (17)0.066*
N10.15274 (14)0.5993 (2)0.47190 (14)0.0279 (4)
N20.07629 (15)0.6835 (2)0.50575 (14)0.0277 (4)
H2N0.088 (2)0.712 (3)0.5686 (14)0.033*
C10.31939 (19)0.4270 (3)0.41219 (17)0.0312 (5)
C20.3994 (2)0.3354 (3)0.39071 (19)0.0402 (6)
H20.40720.32080.32290.048*
C30.4676 (2)0.2657 (3)0.4683 (2)0.0391 (6)
H30.52110.20370.45340.047*
C40.45524 (18)0.2895 (3)0.56914 (18)0.0330 (6)
C50.37678 (18)0.3807 (3)0.59223 (17)0.0319 (5)
H50.37010.39510.66030.038*
C60.30662 (17)0.4524 (3)0.51387 (16)0.0278 (5)
C70.22369 (18)0.5450 (3)0.54062 (17)0.0300 (5)
H70.22190.56560.60940.036*
C8−0.00598 (18)0.7237 (3)0.43815 (16)0.0266 (5)
C9−0.08615 (17)0.8158 (3)0.47789 (16)0.0248 (5)
C10−0.09485 (18)0.8153 (3)0.58150 (16)0.0274 (5)
H10−0.04990.75590.62930.033*
C11−0.17126 (17)0.9044 (3)0.61131 (16)0.0276 (5)
C12−0.23974 (18)0.9932 (3)0.54147 (17)0.0303 (5)
H12−0.29081.05300.56320.036*
C13−0.23079 (18)0.9912 (3)0.43882 (16)0.0291 (5)
C14−0.15405 (17)0.9038 (3)0.40695 (16)0.0283 (5)
H14−0.14790.90400.33810.034*
O20.12746 (16)0.7432 (3)0.72574 (13)0.0428 (5)
H2A0.091 (2)0.772 (4)0.764 (2)0.064*
H2B0.153 (3)0.656 (3)0.750 (2)0.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03931 (19)0.0753 (2)0.04679 (19)0.02026 (15)0.00548 (13)0.01280 (14)
O10.0449 (12)0.0626 (13)0.0261 (9)0.0149 (10)0.0044 (8)−0.0005 (8)
O80.0353 (10)0.0545 (11)0.0224 (8)0.0033 (9)0.0047 (7)−0.0065 (7)
O110.0417 (11)0.0525 (11)0.0209 (8)0.0101 (9)0.0098 (7)0.0018 (7)
O130.0447 (11)0.0571 (12)0.0291 (9)0.0212 (10)0.0033 (8)0.0079 (8)
N10.0269 (11)0.0292 (10)0.0281 (10)0.0012 (9)0.0061 (8)−0.0039 (8)
N20.0273 (11)0.0341 (11)0.0221 (9)0.0035 (9)0.0048 (8)−0.0063 (8)
C10.0308 (13)0.0351 (13)0.0275 (12)0.0001 (11)0.0047 (10)0.0000 (10)
C20.0397 (16)0.0533 (17)0.0302 (13)0.0037 (13)0.0133 (11)−0.0057 (11)
C30.0316 (15)0.0451 (15)0.0431 (15)0.0054 (12)0.0135 (11)−0.0041 (11)
C40.0266 (14)0.0382 (14)0.0338 (13)0.0010 (11)0.0039 (10)0.0021 (10)
C50.0316 (14)0.0382 (13)0.0271 (12)0.0016 (11)0.0082 (10)−0.0020 (10)
C60.0268 (13)0.0294 (12)0.0276 (11)−0.0035 (10)0.0058 (9)−0.0041 (9)
C70.0306 (13)0.0348 (13)0.0251 (11)0.0009 (11)0.0066 (10)−0.0049 (9)
C80.0278 (13)0.0289 (12)0.0233 (12)−0.0034 (10)0.0053 (9)−0.0001 (9)
C90.0243 (12)0.0269 (11)0.0233 (11)−0.0032 (9)0.0041 (9)−0.0015 (9)
C100.0290 (13)0.0307 (12)0.0216 (11)0.0007 (10)0.0015 (9)0.0012 (9)
C110.0301 (13)0.0315 (12)0.0222 (11)−0.0034 (10)0.0072 (9)−0.0009 (9)
C120.0290 (13)0.0327 (13)0.0304 (12)0.0029 (10)0.0080 (10)−0.0006 (9)
C130.0289 (13)0.0299 (12)0.0271 (11)0.0012 (10)0.0008 (10)0.0032 (9)
C140.0322 (14)0.0340 (13)0.0182 (10)−0.0018 (11)0.0034 (9)−0.0002 (9)
O20.0497 (13)0.0487 (11)0.0308 (10)0.0051 (10)0.0093 (8)0.0000 (8)
Geometric parameters (Å, °) top
Br1—C41.899 (2)C4—C51.372 (3)
O1—C11.361 (3)C5—C61.402 (3)
O1—H10.812 (18)C5—H50.9300
O8—C81.244 (3)C6—C71.445 (3)
O11—C111.381 (3)C7—H70.9300
O11—H110.827 (18)C8—C91.487 (3)
O13—C131.361 (3)C9—C141.389 (3)
O13—H130.785 (18)C9—C101.398 (3)
N1—C71.279 (3)C10—C111.375 (3)
N1—N21.379 (3)C10—H100.9300
N2—C81.341 (3)C11—C121.388 (3)
N2—H2N0.851 (17)C12—C131.386 (3)
C1—C21.383 (4)C12—H120.9300
C1—C61.403 (3)C13—C141.383 (3)
C2—C31.375 (4)C14—H140.9300
C2—H20.9300O2—H2A0.807 (18)
C3—C41.389 (3)O2—H2B0.825 (18)
C3—H30.9300
C1—O1—H1110 (2)N1—C7—C6121.5 (2)
C11—O11—H11109 (2)N1—C7—H7119.2
C13—O13—H13108 (3)C6—C7—H7119.2
C7—N1—N2116.85 (18)O8—C8—N2121.5 (2)
C8—N2—N1119.13 (18)O8—C8—C9121.2 (2)
C8—N2—H2N125.0 (18)N2—C8—C9117.29 (18)
N1—N2—H2N115.7 (18)C14—C9—C10120.3 (2)
O1—C1—C2117.4 (2)C14—C9—C8117.02 (19)
O1—C1—C6122.0 (2)C10—C9—C8122.7 (2)
C2—C1—C6120.6 (2)C11—C10—C9118.6 (2)
C3—C2—C1120.9 (2)C11—C10—H10120.7
C3—C2—H2119.6C9—C10—H10120.7
C1—C2—H2119.6C10—C11—O11122.1 (2)
C2—C3—C4118.8 (2)C10—C11—C12121.8 (2)
C2—C3—H3120.6O11—C11—C12116.1 (2)
C4—C3—H3120.6C13—C12—C11118.9 (2)
C5—C4—C3121.3 (2)C13—C12—H12120.5
C5—C4—Br1119.64 (18)C11—C12—H12120.5
C3—C4—Br1119.10 (19)O13—C13—C14122.5 (2)
C4—C5—C6120.5 (2)O13—C13—C12117.0 (2)
C4—C5—H5119.8C14—C13—C12120.4 (2)
C6—C5—H5119.8C13—C14—C9119.91 (19)
C5—C6—C1117.9 (2)C13—C14—H14120.0
C5—C6—C7119.1 (2)C9—C14—H14120.0
C1—C6—C7123.0 (2)H2A—O2—H2B105 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.81 (2)1.95 (2)2.657 (2)145 (3)
N2—H2N···O20.85 (2)2.07 (2)2.913 (3)170 (2)
O1—H1···O2i0.81 (2)2.52 (3)2.942 (3)114 (3)
O11—H11···O8ii0.83 (2)1.94 (2)2.750 (2)168 (3)
O13—H13···O1iii0.79 (2)2.19 (2)2.959 (2)165 (3)
O2—H2A···O8ii0.81 (2)1.98 (2)2.776 (3)171 (4)
O2—H2B···O11iv0.83 (2)2.06 (2)2.861 (3)165 (3)
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, y−1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.81 (2)1.95 (2)2.657 (2)145 (3)
N2—H2N···O20.85 (2)2.07 (2)2.913 (3)170 (2)
O11—H11···O8i0.83 (2)1.94 (2)2.750 (2)168 (3)
O13—H13···O1ii0.79 (2)2.19 (2)2.959 (2)165 (3)
O2—H2A···O8i0.81 (2)1.98 (2)2.776 (3)171 (4)
O2—H2B···O11iii0.83 (2)2.06 (2)2.861 (3)165 (3)
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+3/2.
Acknowledgements top

The authors thank the University of Malaya for funding this study (FRGS grant No. FP009/2008 C)

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Deng, S., Han, L., Huang, S., Zhang, H., Diao, Y. & Liu, K. (2009). Acta Cryst. E65, o721.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.