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Acta Crystallogr Sect E Struct Rep Online. Aug 1, 2010; 66(Pt 8): o2014.
Published online Jul 14, 2010. doi:  10.1107/S160053681002698X
PMCID: PMC3007216
4-Bromo-2-({4-[(hy­droxy­imino)­meth­yl]phen­yl}imino­meth­yl)phenol
Yu-Hua Yang,a* Jian-Chao Wu,a Shang-Sheng Gong,a and Jiu-Si Wanga
aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People’s Republic of China
Correspondence e-mail: yangyh70/at/163.com
Received June 11, 2010; Accepted July 8, 2010.
Abstract
In the title compound, C14H11BrN2O2, the mean planes of the two benzene rings are almost parallel to each other, making a dihedral angle of 4.09 (1)°. An intra­molecular O—H(...)N hydrogen bond occurs. In the crystal, inter­molecular O—H(...)N and C—H(...)O hydrogen bonds link the mol­ecules into a chain-like supra­molecular structure.
Related literature
For background to the use of Schiff bases as ligands in coord­ination chemistry, see: Biswas et al. (2008 [triangle]); Dong et al. (2010 [triangle]). For the synthesis of the title compound and related structures, see: Dong et al. (2007 [triangle], 2009 [triangle]); Zhao et al. (2009 [triangle]).
An external file that holds a picture, illustration, etc.
Object name is e-66-o2014-scheme1.jpg Object name is e-66-o2014-scheme1.jpg
Crystal data
  • C14H11BrN2O2
  • M r = 319.16
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2014-efi1.jpg
  • a = 4.4279 (5) Å
  • b = 12.1790 (16) Å
  • c = 23.196 (2) Å
  • V = 1250.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.29 mm−1
  • T = 113 K
  • 0.26 × 0.24 × 0.22 mm
Data collection
  • Rigaku Saturn724 CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009 [triangle]) T min = 0.482, T max = 0.532
  • 15336 measured reflections
  • 4346 independent reflections
  • 2818 reflections with I > 2σ(I)
  • R int = 0.048
Refinement
  • R[F 2 > 2σ(F 2)] = 0.027
  • wR(F 2) = 0.054
  • S = 0.85
  • 4346 reflections
  • 180 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.88 e Å−3
  • Δρmin = −0.44 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1615 Friedel pairs
  • Flack parameter: −0.022 (7)
Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009 [triangle]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: CrystalStructure (Rigaku/MSC, 2009 [triangle]); software used to prepare material for publication: CrystalStructure.
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002698X/pv2295sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S160053681002698X/pv2295Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
This work was supported by the Foundation of the Education Department of Gansu Province (No. 0904–11) and the ‘JingLan’ Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.
supplementary crystallographic information
Comment
Schiff bases have been used widely as versatile ligands in coordination chemistry (Biswas et al., 2008; Dong et al., 2010). Recently, the structures of a few Schiff base compounds have been reported (Dong et al., 2007; Dong et al., 2009). In this paper, we report the synthesis and crystal structure of the title compound, (I).
In the title compound (Fig. 1) the bond lengths and angles are in normal ranges and agree very well with the corresponding bond lengths and angles reported in similar structures (Dong et al., 2007; Dong et al., 2009; Zhao et al., 2009). The mean planes of the two benzene rings are almost parallel to each other making a dihedral angle of 4.09 (1) ° with respect to each other. There is an intramolecular hydrogen bond, O1—H1···N1 (Tab. 1). Besides, intermolecular hydrogen bonds, O2—H2···N2 and C5—H5···O2 link molecules into infinite catenarian supramolecular shape (Tab. 1 & Fig. 2).
Experimental
The title compound was synthesized according to methods reported earlier (Zhao et al., 2009; Dong et al., 2009). A solution of 1-(4-aminophenyl)-methanal (1.21 g, 10 mmol) in methanol (15 ml) was added to a mixture of hydroxylamine sulfate (1.31 g, 10 mmol) and sodium acetate (2.0 g, 25 mmol). After refluxing for 4–5 h, the reaction was completed. The solvent was evaporated under vacuo. Demineralized water (40 ml) was added, cooled to 268–265 K and filtered, resulting in 4-aminobenzaldehyde oxime as a crystalline solid (yield; 1.18 g, 86.7%; m.p. 395–397 K). To an ethalnol solution (5 ml) of 4-aminobenzaldehyde oxime (0.1362 g, 1 mmol) was added dropwise an ethanol solution (5 ml) of 5-bromo-2-hydroxybenzaldehyde (0.19995 g, 1 mmol). The mixture solution was stirred at 328–333 K for 5 h. After cooling to room temperature, the precipitate was filtered off, and washed successively three times with ethanol. The product was dried in vacuo and purified by recrystallization from ethanol to yield 267.5 mg (Yield, 83.8%) of solid; m.p. 490–491 K. Pale-yellow needle-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of methanol at room temperature in about one month.
Refinement
An absolute structure was determined by Flack (1983) method employing 1615 Friedel pairs. H atoms were treated as riding atoms with distances C—H = 0.95 Å and Uiso(H) = 1.2 Ueq(C). The hydroxyl H-atoms were located from a difference Fourier map and were allowed to refine freely.
Figures
Fig. 1.
Fig. 1.
The molecule structure of the title complex with atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Fig. 2.
Unit cell packing of the title compound. Intramolecular and intermolecular hydrogen bonds are shown as dashed lines.
Crystal data
C14H11BrN2O2Dx = 1.695 Mg m3
Mr = 319.16Melting point = 490–491 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2abCell parameters from 4929 reflections
a = 4.4279 (5) Åθ = 1.9–32.9°
b = 12.1790 (16) ŵ = 3.29 mm1
c = 23.196 (2) ÅT = 113 K
V = 1250.9 (3) Å3Needle, pale-yellow
Z = 40.26 × 0.24 × 0.22 mm
F(000) = 640
Data collection
Rigaku Saturn724 CCD diffractometer4346 independent reflections
Radiation source: Rotating Anode2818 reflections with I > 2σ(I)
multilayerRint = 0.048
Detector resolution: 14.222 pixels mm-1θmax = 32.9°, θmin = 1.8°
ω scansh = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)k = −18→17
Tmin = 0.482, Tmax = 0.532l = −34→33
15336 measured reflections
Refinement
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.054w = 1/[σ2(Fo2) + (0.0171P)2] where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max = 0.001
4346 reflectionsΔρmax = 0.88 e Å3
180 parametersΔρmin = −0.44 e Å3
0 restraintsAbsolute structure: Flack (1983), 1615 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.022 (7)
Special details
Experimental. Anal. Calc. for C14H11BrN2O2: C, 52.69; H, 3.47; N, 8.78. Found: C, 52.67; H, 3.44; N, 8.81.
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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
xyzUiso*/Ueq
Br10.93894 (6)0.310770 (17)0.055477 (9)0.02449 (6)
O10.5216 (4)0.65997 (11)0.22190 (6)0.0219 (4)
O2−0.9560 (4)0.35901 (13)0.51519 (6)0.0228 (4)
N10.1808 (4)0.51372 (14)0.27053 (7)0.0158 (4)
N2−0.7439 (4)0.34661 (14)0.47039 (7)0.0165 (4)
C10.6150 (5)0.57912 (16)0.18617 (8)0.0156 (5)
C20.5081 (5)0.46983 (15)0.19213 (8)0.0150 (5)
C30.6111 (5)0.38957 (16)0.15310 (8)0.0174 (5)
H30.54290.31590.15650.021*
C40.8098 (5)0.41758 (17)0.11007 (9)0.0181 (5)
C50.9174 (5)0.52501 (16)0.10466 (8)0.0174 (4)
H51.05710.54310.07510.021*
C60.8195 (5)0.60434 (17)0.14244 (9)0.0189 (5)
H60.89220.67740.13870.023*
C70.2943 (5)0.44092 (17)0.23670 (9)0.0172 (5)
H70.23620.36630.24110.021*
C8−0.0289 (5)0.48808 (15)0.31419 (8)0.0142 (4)
C9−0.1308 (5)0.57570 (17)0.34784 (9)0.0181 (5)
H9−0.05800.64770.34050.022*
C10−0.3373 (5)0.55866 (17)0.39193 (9)0.0185 (5)
H10−0.40720.61950.41380.022*
C11−0.4435 (5)0.45385 (15)0.40458 (8)0.0154 (4)
C12−0.3426 (5)0.36586 (16)0.37064 (9)0.0175 (5)
H12−0.41390.29380.37830.021*
C13−0.1407 (5)0.38292 (16)0.32620 (8)0.0170 (5)
H13−0.07660.32250.30340.020*
C14−0.6628 (5)0.44081 (17)0.45110 (9)0.0171 (5)
H14−0.74890.50480.46780.021*
H10.384 (5)0.6368 (17)0.2459 (9)0.022 (7)*
H2−1.018 (7)0.302 (2)0.5186 (12)0.070 (12)*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
Br10.03228 (13)0.02054 (9)0.02065 (10)0.00167 (11)0.00598 (11)−0.00300 (9)
O10.0290 (11)0.0162 (7)0.0204 (8)−0.0007 (7)0.0061 (8)−0.0010 (6)
O20.0245 (10)0.0219 (8)0.0220 (8)−0.0066 (8)0.0081 (8)−0.0010 (6)
N10.0149 (10)0.0174 (9)0.0150 (9)0.0026 (8)−0.0014 (8)0.0015 (7)
N20.0123 (10)0.0234 (10)0.0138 (8)−0.0013 (7)0.0002 (8)−0.0013 (7)
C10.0158 (13)0.0163 (10)0.0146 (10)0.0027 (9)−0.0017 (9)−0.0003 (8)
C20.0134 (14)0.0171 (9)0.0146 (9)0.0017 (8)−0.0016 (9)0.0026 (7)
C30.0174 (14)0.0151 (10)0.0196 (11)−0.0007 (9)−0.0048 (10)0.0005 (8)
C40.0184 (13)0.0202 (11)0.0157 (10)0.0042 (9)−0.0025 (10)−0.0015 (9)
C50.0149 (12)0.0215 (10)0.0157 (10)0.0002 (10)0.0016 (11)0.0023 (8)
C60.0217 (13)0.0148 (10)0.0201 (11)−0.0032 (9)−0.0022 (10)0.0014 (8)
C70.0159 (12)0.0164 (10)0.0194 (11)−0.0005 (9)−0.0019 (10)0.0015 (9)
C80.0112 (12)0.0177 (9)0.0136 (9)−0.0004 (9)−0.0016 (9)0.0009 (7)
C90.0186 (14)0.0149 (10)0.0209 (11)0.0001 (9)0.0010 (10)0.0005 (8)
C100.0210 (13)0.0168 (10)0.0178 (11)0.0031 (9)−0.0005 (10)−0.0037 (8)
C110.0129 (11)0.0199 (10)0.0134 (9)−0.0015 (10)−0.0030 (10)−0.0001 (7)
C120.0195 (13)0.0140 (10)0.0190 (10)0.0003 (9)−0.0009 (10)0.0027 (8)
C130.0189 (14)0.0151 (10)0.0170 (10)0.0028 (9)−0.0033 (9)−0.0012 (8)
C140.0161 (11)0.0184 (10)0.0169 (11)0.0001 (8)−0.0019 (10)−0.0024 (9)
Geometric parameters (Å, °)
Br1—C41.903 (2)C5—H50.9500
O1—C11.352 (2)C6—H60.9500
O1—H10.87 (2)C7—H70.9500
O2—N21.409 (2)C8—C91.397 (3)
O2—H20.75 (3)C8—C131.401 (3)
N1—C71.286 (2)C9—C101.387 (3)
N1—C81.409 (3)C9—H90.9500
N2—C141.283 (2)C10—C111.392 (3)
C1—C61.394 (3)C10—H100.9500
C1—C21.419 (3)C11—C121.403 (3)
C2—C31.408 (3)C11—C141.460 (3)
C2—C71.445 (3)C12—C131.380 (3)
C3—C41.374 (3)C12—H120.9500
C3—H30.9500C13—H130.9500
C4—C51.398 (3)C14—H140.9500
C5—C61.375 (3)
C1—O1—H1111.7 (14)N1—C7—H7119.2
N2—O2—H2103 (2)C2—C7—H7119.2
C7—N1—C8122.91 (18)C9—C8—C13118.23 (19)
C14—N2—O2110.38 (17)C9—C8—N1116.44 (18)
O1—C1—C6118.97 (18)C13—C8—N1125.33 (18)
O1—C1—C2121.43 (19)C10—C9—C8120.70 (19)
C6—C1—C2119.60 (18)C10—C9—H9119.6
C3—C2—C1118.72 (19)C8—C9—H9119.6
C3—C2—C7120.18 (18)C9—C10—C11121.0 (2)
C1—C2—C7121.09 (18)C9—C10—H10119.5
C4—C3—C2120.14 (19)C11—C10—H10119.5
C4—C3—H3119.9C10—C11—C12118.3 (2)
C2—C3—H3119.9C10—C11—C14118.71 (18)
C3—C4—C5121.05 (19)C12—C11—C14122.92 (18)
C3—C4—Br1120.41 (16)C13—C12—C11120.70 (19)
C5—C4—Br1118.53 (16)C13—C12—H12119.7
C6—C5—C4119.5 (2)C11—C12—H12119.7
C6—C5—H5120.2C12—C13—C8120.99 (19)
C4—C5—H5120.2C12—C13—H13119.5
C5—C6—C1120.93 (19)C8—C13—H13119.5
C5—C6—H6119.5N2—C14—C11122.78 (18)
C1—C6—H6119.5N2—C14—H14118.6
N1—C7—C2121.63 (19)C11—C14—H14118.6
O1—C1—C2—C3179.22 (19)C7—N1—C8—C9179.5 (2)
C6—C1—C2—C3−0.5 (3)C7—N1—C8—C13−0.4 (3)
O1—C1—C2—C70.1 (3)C13—C8—C9—C100.0 (3)
C6—C1—C2—C7−179.5 (2)N1—C8—C9—C10−179.95 (19)
C1—C2—C3—C4−0.3 (3)C8—C9—C10—C111.3 (3)
C7—C2—C3—C4178.75 (19)C9—C10—C11—C12−1.6 (3)
C2—C3—C4—C51.0 (3)C9—C10—C11—C14−179.44 (19)
C2—C3—C4—Br1−177.75 (16)C10—C11—C12—C130.6 (3)
C3—C4—C5—C6−1.0 (3)C14—C11—C12—C13178.34 (19)
Br1—C4—C5—C6177.87 (17)C11—C12—C13—C80.7 (3)
C4—C5—C6—C10.1 (3)C9—C8—C13—C12−1.0 (3)
O1—C1—C6—C5−179.1 (2)N1—C8—C13—C12178.95 (19)
C2—C1—C6—C50.5 (3)O2—N2—C14—C11179.74 (18)
C8—N1—C7—C2179.75 (19)C10—C11—C14—N2−171.1 (2)
C3—C2—C7—N1−175.3 (2)C12—C11—C14—N211.2 (3)
C1—C2—C7—N13.8 (3)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.87 (2)1.84 (2)2.593 (2)143 (2)
O2—H2···N2i0.75 (3)2.08 (3)2.830 (2)173 (2)
C5—H5···O2ii0.952.543.463 (3)163
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1/2, −y+1, z−1/2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2295).
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