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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o2022.
Published online 2008 September 27. doi:  10.1107/S1600536808030304
PMCID: PMC2959471

(E)-N′-(3,5-Dibromo-2-hydroxy­benzyl­idene)-4-hydroxy­benzohydrazide monohydrate

Abstract

The title compound, C14H10Br2N2O3·H2O, was synthesized by the reaction of 3,5-dibromo-2-hydroxy­benzaldehyde with an equimolar amount of 4-hydroxy­benzohydrazide in methanol. The structure comprises a Schiff base unit and a water mol­ecule of crystallization. The dihedral angle between the benzene rings in the Schiff base is 1.3 (3)°. In the crystal structure, mol­ecules are linked through inter­molecular O—H(...)O and N—H(...)O hydrogen bonds, with the water mol­ecule serving as both donor and acceptor. As a result, layers are formed, which are approximately parallel to the bc plane.

Related literature

For related structures, see: Cao (2007a [triangle],b [triangle]); Yang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2022-scheme1.jpg

Experimental

Crystal data

  • C14H10Br2N2O3·H2O
  • M r = 432.08
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2022-efi1.jpg
  • a = 6.9840 (16) Å
  • b = 12.678 (3) Å
  • c = 17.722 (4) Å
  • β = 96.999 (4)°
  • V = 1557.4 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 5.22 mm−1
  • T = 298 (2) K
  • 0.23 × 0.23 × 0.22 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.307, T max = 0.318
  • 12695 measured reflections
  • 3366 independent reflections
  • 2045 reflections with I > 2σ(I)
  • R int = 0.075

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.106
  • S = 0.99
  • 3366 reflections
  • 210 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.42 e Å−3
  • Δρmin = −0.42 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/S1600536808030304/bh2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030304/bh2193Isup2.hkl

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

Acknowledgments

The Natural Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 07JK177) is acknowledged.

supplementary crystallographic information

Comment

We have recently reported some transition metal complexes with Schiff base ligands (Cao, 2007a; Cao, 2007b). We report herein the crystal structure of the title compound, (I), derived from the reaction of 3,5-dibromo-2-hydroxybenzaldehyde with an equimolar quantity of 4-hydroxybenzohydrazide in methanol.

The compound (I), Fig. 1, comprises a Schiff base unit and a water molecule of crystallization. The dihedral angle between the two benzene rings in the Schiff base unit is 1.3 (3)°. All bond lengths are comparable to the similar compound, 3-bromo-N'-[(E)-4-hydroxybenzylidene]benzohydrazide, which we reported previously (Yang et al., 2008). In the crystal structure, molecules are linked through intermolecular hydrogen bonds of types O—H···O and N—H···O (Table 1), forming 2D layers approximately parallel to the bc plane, as shown in Fig. 2.

Experimental

The compound was prepared by refluxing equimolar quantities of 3,5-dibromo-2-hydroxybenzaldehyde with 4-hydroxybenzohydrazide in methanol. Colorless block crystals were formed when the solution was evaporated in air over five days.

Refinement

Water H atoms and H2 were located in a difference map and refined isotropically, with O—H, N—H, and H···H distances restrained to 0.85 (1), 0.90 (1), and 1.37 (2) Å, respectively. The other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93 Å and O—H distance of 0.82 Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I) with ellipsoids drawn at the 30% probability level. Water and main molecule are placed in two different asymmetric units.
Fig. 2.
The molecular packing of (I), viewed along the c axis. Hydrogen bonds are drawn as dashed lines.

Crystal data

C14H10Br2N2O3·H2OF(000) = 848
Mr = 432.08Dx = 1.843 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1545 reflections
a = 6.9840 (16) Åθ = 2.3–24.9°
b = 12.678 (3) ŵ = 5.22 mm1
c = 17.722 (4) ÅT = 298 K
β = 96.999 (4)°Block, colourless
V = 1557.4 (6) Å30.23 × 0.23 × 0.22 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3366 independent reflections
Radiation source: fine-focus sealed tube2045 reflections with I > 2σ(I)
graphiteRint = 0.075
ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −8→8
Tmin = 0.308, Tmax = 0.318k = −16→15
12695 measured reflectionsl = −22→22

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0361P)2] where P = (Fo2 + 2Fc2)/3
3366 reflections(Δ/σ)max = 0.001
210 parametersΔρmax = 0.42 e Å3
4 restraintsΔρmin = −0.42 e Å3
0 constraints

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

xyzUiso*/Ueq
Br10.07183 (8)0.86697 (4)−0.00493 (3)0.0601 (2)
Br20.05286 (8)0.71867 (5)−0.30593 (3)0.0664 (2)
O10.1871 (5)0.6446 (2)0.03203 (16)0.0405 (7)
H10.21900.58340.04200.061*
O20.3386 (4)0.4075 (2)0.14777 (16)0.0426 (8)
O30.5946 (6)−0.0702 (2)0.20309 (16)0.0594 (10)
H30.6086−0.07330.24970.089*
O40.4571 (5)0.2539 (3)0.39995 (18)0.0494 (8)
N10.2698 (5)0.4520 (3)0.00247 (19)0.0323 (8)
N20.3257 (5)0.3529 (3)0.02714 (19)0.0336 (8)
C10.1784 (6)0.5746 (3)−0.0955 (2)0.0301 (10)
C20.1564 (6)0.6572 (3)−0.0440 (2)0.0336 (10)
C30.1013 (6)0.7560 (3)−0.0737 (3)0.0388 (11)
C40.0691 (6)0.7749 (4)−0.1503 (3)0.0422 (11)
H40.03230.8414−0.16870.051*
C50.0927 (6)0.6928 (4)−0.1997 (2)0.0385 (11)
C60.1470 (6)0.5942 (4)−0.1731 (2)0.0398 (11)
H60.16280.5401−0.20730.048*
C70.2368 (6)0.4704 (3)−0.0687 (2)0.0358 (10)
H70.25040.4166−0.10330.043*
C80.3580 (6)0.3355 (3)0.1033 (2)0.0311 (10)
C90.4152 (6)0.2264 (3)0.1270 (2)0.0292 (9)
C100.4475 (7)0.2041 (3)0.2037 (2)0.0430 (12)
H100.42940.25730.23830.052*
C110.5056 (7)0.1059 (3)0.2311 (2)0.0438 (12)
H110.52620.09330.28320.053*
C120.5325 (7)0.0275 (3)0.1807 (2)0.0385 (11)
C130.4980 (7)0.0477 (3)0.1040 (2)0.0528 (14)
H130.5146−0.00590.06960.063*
C140.4397 (7)0.1452 (3)0.0773 (2)0.0462 (12)
H140.41630.15690.02520.055*
H20.356 (7)0.307 (3)−0.008 (2)0.080*
H4A0.436 (6)0.309 (3)0.373 (3)0.080*
H4B0.5787 (19)0.245 (4)0.408 (3)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0799 (4)0.0359 (3)0.0643 (4)0.0158 (3)0.0076 (3)−0.0051 (3)
Br20.0707 (4)0.0883 (5)0.0380 (3)0.0029 (3)−0.0022 (2)0.0233 (3)
O10.061 (2)0.0292 (17)0.0304 (16)0.0048 (16)0.0005 (15)0.0034 (13)
O20.066 (2)0.0267 (16)0.0348 (17)0.0075 (15)0.0035 (15)−0.0053 (14)
O30.122 (3)0.0215 (17)0.0333 (18)0.0134 (19)0.003 (2)0.0046 (14)
O40.070 (2)0.041 (2)0.0359 (18)−0.0058 (18)0.0031 (17)0.0069 (15)
N10.035 (2)0.026 (2)0.034 (2)0.0008 (16)0.0007 (16)0.0021 (16)
N20.046 (2)0.023 (2)0.031 (2)0.0049 (17)0.0024 (17)0.0037 (15)
C10.032 (2)0.032 (2)0.026 (2)0.0011 (19)0.0028 (18)0.0022 (19)
C20.032 (2)0.035 (3)0.033 (2)0.001 (2)0.0032 (19)0.004 (2)
C30.039 (3)0.030 (2)0.047 (3)0.004 (2)0.004 (2)0.001 (2)
C40.041 (3)0.035 (3)0.050 (3)0.006 (2)0.001 (2)0.016 (2)
C50.035 (2)0.049 (3)0.030 (2)0.000 (2)0.0011 (19)0.015 (2)
C60.042 (3)0.045 (3)0.032 (2)0.004 (2)0.001 (2)0.000 (2)
C70.043 (3)0.032 (3)0.032 (2)0.003 (2)0.002 (2)−0.0007 (19)
C80.029 (2)0.029 (2)0.034 (2)−0.0019 (19)0.0004 (19)0.000 (2)
C90.034 (2)0.023 (2)0.030 (2)−0.0003 (19)0.0010 (18)0.0003 (18)
C100.067 (3)0.033 (3)0.030 (2)0.007 (2)0.006 (2)−0.010 (2)
C110.073 (3)0.032 (3)0.026 (2)0.009 (2)0.006 (2)0.001 (2)
C120.064 (3)0.019 (2)0.033 (3)0.003 (2)0.009 (2)0.0036 (19)
C130.104 (4)0.025 (3)0.029 (3)0.014 (3)0.006 (3)−0.008 (2)
C140.081 (4)0.030 (3)0.026 (2)0.009 (3)0.001 (2)−0.001 (2)

Geometric parameters (Å, °)

Br1—C31.888 (4)C3—C41.371 (6)
Br2—C51.897 (4)C4—C51.382 (6)
O1—C21.348 (5)C4—H40.9300
O1—H10.8200C5—C61.374 (6)
O2—C81.225 (5)C6—H60.9300
O3—C121.355 (5)C7—H70.9300
O3—H30.8200C8—C91.486 (5)
O4—H4A0.847 (10)C9—C141.379 (5)
O4—H4B0.851 (10)C9—C101.379 (6)
N1—C71.275 (5)C10—C111.380 (6)
N1—N21.371 (4)C10—H100.9300
N2—C81.359 (5)C11—C121.365 (6)
N2—H20.898 (10)C11—H110.9300
C1—C61.387 (5)C12—C131.375 (6)
C1—C21.411 (6)C13—C141.368 (6)
C1—C71.446 (6)C13—H130.9300
C2—C31.395 (6)C14—H140.9300
C2—O1—H1109.5N1—C7—C1120.2 (4)
C12—O3—H3109.5N1—C7—H7119.9
H4A—O4—H4B108 (2)C1—C7—H7119.9
C7—N1—N2119.5 (4)O2—C8—N2120.0 (4)
C8—N2—N1118.2 (3)O2—C8—C9123.9 (4)
C8—N2—H2124 (4)N2—C8—C9116.1 (4)
N1—N2—H2117 (4)C14—C9—C10117.3 (4)
C6—C1—C2119.4 (4)C14—C9—C8124.3 (4)
C6—C1—C7119.6 (4)C10—C9—C8118.4 (4)
C2—C1—C7120.9 (4)C9—C10—C11122.5 (4)
O1—C2—C3119.1 (4)C9—C10—H10118.7
O1—C2—C1122.8 (4)C11—C10—H10118.7
C3—C2—C1118.1 (4)C12—C11—C10119.0 (4)
C4—C3—C2122.3 (4)C12—C11—H11120.5
C4—C3—Br1119.5 (3)C10—C11—H11120.5
C2—C3—Br1118.2 (3)O3—C12—C11122.6 (4)
C3—C4—C5118.6 (4)O3—C12—C13118.1 (4)
C3—C4—H4120.7C11—C12—C13119.3 (4)
C5—C4—H4120.7C14—C13—C12121.3 (4)
C6—C5—C4121.1 (4)C14—C13—H13119.4
C6—C5—Br2120.0 (4)C12—C13—H13119.4
C4—C5—Br2118.9 (3)C13—C14—C9120.6 (4)
C5—C6—C1120.5 (4)C13—C14—H14119.7
C5—C6—H6119.7C9—C14—H14119.7
C1—C6—H6119.7

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.578 (4)146.
O3—H3···O2i0.821.832.642 (4)173.
O4—H4A···O3ii0.85 (1)2.04 (1)2.878 (4)171 (5)
O4—H4B···O1i0.85 (1)2.24 (3)2.969 (5)144 (4)
N2—H2···O4iii0.90 (1)2.01 (2)2.874 (5)162 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2193).

References

  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cao, G.-B. (2007a). Synth. React. Inorg. Met. Org. Nano-Met. Chem.37, 639–642.
  • Cao, G.-B. (2007b). Acta Cryst. E63, m1149–m1150.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. [PMC free article] [PubMed]

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