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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2045.
Published online 2010 July 17. doi:  10.1107/S1600536810027856
PMCID: PMC3007438

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

Abstract

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.

Related literature

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

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Object name is e-66-o2045-scheme1.jpg

Experimental

Crystal data

  • C14H11BrN2O4·H2O
  • M r = 369.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2045-efi1.jpg
  • a = 13.5685 (3) Å
  • b = 8.0532 (2) Å
  • c = 13.2447 (2) Å
  • β = 100.186 (1)°
  • V = 1424.44 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.91 mm−1
  • T = 296 K
  • 0.58 × 0.33 × 0.06 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.283, T max = 0.845
  • 9148 measured reflections
  • 2579 independent reflections
  • 2183 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.077
  • S = 1.04
  • 2579 reflections
  • 217 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.56 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: SHELXL97 and publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810027856/bh2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027856/bh2299Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.
Thermal ellipsoid plot of the title compound at 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Packing view looking down the crystallographic b unit cell edge.

Crystal data

C14H11BrN2O4·H2OF(000) = 744
Mr = 369.17Dx = 1.721 Mg m3
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 mm1
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

Bruker APEXII CCD diffractometer2579 independent reflections
Radiation source: fine-focus sealed tube2183 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] 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

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 = 1.04w = 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 Å3
6 restraintsΔρmin = −0.56 e Å3
0 constraints

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2299).

References

  • 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. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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