Acta Cryst. (2008). E64, o1938 [ doi:10.1107/S160053680802905X ]
The molecule of the title compound, C14H10BrClN2O3, is planar [dihedral angle between the aromatic rings = 3.0 (2)°] and shows a trans configuration with respect to the C=N double bond. The crystal structure is stabilized by intermolecular N-H
O hydrogen bonds and an intramolecular O-HN interaction also occurs.
3-Bromo-5-chlorosalicylaldehyde and 4-hydroxybenzohydrazide of AR grade were purchased from Aldrich and were used as was obtained. 3-Bromo-5-chlorosalicylaldehyde (235.3 mg, 1.0 mmol) and 4-hydroxybenzohydrazide (152.2 mg, 1.0 mmol) were dissolved in a methanol solution (80 ml). The mixture was stirred for two hours at room temperature. The resulting solution was left in air for a few days, yielding colourless block-like crystals.
H2 was located in a difference Fourier map and refined isotropically, with N—H distance restrained to 0.90 (3)Å, and with Uiso(H) fixed at 0.08Å2. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms with C—H distances of 0.93Å, O—H distance of 0.82Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(O).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./bx2178fig1thm.gif)
| Fig. 1. The structure of (I) with 30% probability displacement ellipsoids. dashed lines indicate intramolecular hydrogen bonds. |
![[Figure 2]](./bx2178fig2thm.gif)
| Fig. 2. The molecular packing of (I). Intermolecular hydrogen bonds are shown as dashed lines. H atoms unrelated to the hydrogen bonding have been omitted for clarity. |
| C14H10BrClN2O3 | F(000) = 736 |
| Mr = 369.60 | Dx = 1.749 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.279 (2) Å | Cell parameters from 2405 reflections |
| b = 11.446 (3) Å | θ = 2.3–24.6° |
| c = 14.998 (4) Å | µ = 3.13 mm−1 |
| β = 99.002 (4)° | T = 298 K |
| V = 1403.7 (6) Å3 | Block, colourless |
| Z = 4 | 0.17 × 0.15 × 0.15 mm |
| Bruker SMART CCD area-detector diffractometer | 3006 independent reflections |
| Radiation source: fine-focus sealed tube | 2102 reflections with I > 2σ(I) |
| graphite | Rint = 0.049 |
| ω scans | θmax = 27.0°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
| Tmin = 0.618, Tmax = 0.651 | k = −14→14 |
| 10685 measured reflections | l = −19→19 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.1022P] where P = (Fo2 + 2Fc2)/3 |
| 3006 reflections | (Δ/σ)max = 0.001 |
| 195 parameters | Δρmax = 0.50 e Å−3 |
| 1 restraint | Δρmin = −0.36 e Å−3 |
| C14H10BrClN2O3 | V = 1403.7 (6) Å3 |
| Mr = 369.60 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 8.279 (2) Å | µ = 3.13 mm−1 |
| b = 11.446 (3) Å | T = 298 K |
| c = 14.998 (4) Å | 0.17 × 0.15 × 0.15 mm |
| β = 99.002 (4)° |
| Bruker SMART CCD area-detector diffractometer | 3006 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2102 reflections with I > 2σ(I) |
| Tmin = 0.618, Tmax = 0.651 | Rint = 0.049 |
| 10685 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.100 | Δρmax = 0.50 e Å−3 |
| S = 1.03 | Δρmin = −0.36 e Å−3 |
| 3006 reflections | Absolute structure: ? |
| 195 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
| x | y | z | Uiso*/Ueq | ||
| Br1 | 1.16504 (5) | 0.88843 (3) | 1.28591 (2) | 0.05440 (17) | |
| Cl1 | 1.19663 (10) | 0.56024 (7) | 1.02050 (6) | 0.0436 (2) | |
| N1 | 0.7282 (3) | 0.9996 (2) | 0.98662 (16) | 0.0299 (6) | |
| N2 | 0.6142 (3) | 1.0530 (2) | 0.92314 (15) | 0.0303 (6) | |
| O1 | 0.9168 (3) | 0.98960 (19) | 1.14418 (14) | 0.0409 (5) | |
| H1 | 0.8479 | 1.0183 | 1.1051 | 0.061* | |
| O2 | 0.5803 (3) | 1.20014 (17) | 1.01833 (13) | 0.0387 (5) | |
| O3 | 0.0964 (3) | 1.38132 (18) | 0.68220 (14) | 0.0426 (6) | |
| H3 | 0.0978 | 1.3553 | 0.6314 | 0.064* | |
| C1 | 0.9178 (3) | 0.8455 (2) | 1.02657 (18) | 0.0275 (6) | |
| C2 | 0.9719 (3) | 0.8893 (2) | 1.11358 (19) | 0.0278 (6) | |
| C3 | 1.0902 (4) | 0.8268 (3) | 1.17019 (18) | 0.0314 (7) | |
| C4 | 1.1560 (4) | 0.7256 (3) | 1.1431 (2) | 0.0351 (7) | |
| H4 | 1.2341 | 0.6847 | 1.1824 | 0.042* | |
| C5 | 1.1051 (4) | 0.6856 (3) | 1.0573 (2) | 0.0323 (7) | |
| C6 | 0.9868 (4) | 0.7438 (3) | 0.9991 (2) | 0.0324 (7) | |
| H6 | 0.9532 | 0.7149 | 0.9412 | 0.039* | |
| C7 | 0.7930 (4) | 0.9061 (3) | 0.9632 (2) | 0.0327 (7) | |
| H7 | 0.7610 | 0.8760 | 0.9056 | 0.039* | |
| C8 | 0.5482 (4) | 1.1559 (3) | 0.94328 (19) | 0.0283 (7) | |
| C9 | 0.4350 (3) | 1.2130 (2) | 0.87016 (17) | 0.0258 (6) | |
| C10 | 0.3617 (4) | 1.3161 (3) | 0.89023 (19) | 0.0344 (7) | |
| H10 | 0.3888 | 1.3482 | 0.9476 | 0.041* | |
| C11 | 0.2498 (4) | 1.3723 (3) | 0.8275 (2) | 0.0375 (8) | |
| H11 | 0.2009 | 1.4412 | 0.8426 | 0.045* | |
| C12 | 0.2103 (4) | 1.3258 (3) | 0.74178 (18) | 0.0287 (7) | |
| C13 | 0.2856 (4) | 1.2251 (3) | 0.71958 (18) | 0.0349 (7) | |
| H13 | 0.2615 | 1.1948 | 0.6615 | 0.042* | |
| C14 | 0.3965 (4) | 1.1692 (3) | 0.78333 (19) | 0.0339 (7) | |
| H14 | 0.4465 | 1.1009 | 0.7679 | 0.041* | |
| H2 | 0.577 (5) | 1.016 (3) | 0.8710 (15) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.0585 (3) | 0.0637 (3) | 0.0345 (2) | 0.00635 (19) | −0.01299 (16) | −0.01098 (17) |
| Cl1 | 0.0499 (5) | 0.0294 (4) | 0.0502 (5) | 0.0096 (4) | 0.0043 (4) | −0.0043 (4) |
| N1 | 0.0290 (13) | 0.0281 (14) | 0.0296 (13) | −0.0019 (11) | −0.0045 (10) | 0.0072 (11) |
| N2 | 0.0334 (14) | 0.0286 (14) | 0.0251 (13) | 0.0009 (11) | −0.0071 (10) | 0.0026 (11) |
| O1 | 0.0468 (14) | 0.0366 (13) | 0.0358 (13) | 0.0113 (11) | −0.0046 (10) | −0.0055 (10) |
| O2 | 0.0562 (14) | 0.0317 (12) | 0.0229 (11) | −0.0037 (10) | −0.0105 (9) | 0.0004 (9) |
| O3 | 0.0609 (15) | 0.0360 (13) | 0.0264 (11) | 0.0180 (11) | −0.0070 (11) | 0.0015 (9) |
| C1 | 0.0285 (16) | 0.0244 (16) | 0.0278 (15) | −0.0028 (13) | −0.0009 (12) | 0.0029 (12) |
| C2 | 0.0281 (16) | 0.0255 (16) | 0.0288 (15) | −0.0008 (13) | 0.0006 (12) | −0.0007 (12) |
| C3 | 0.0298 (16) | 0.0368 (18) | 0.0251 (15) | −0.0048 (14) | −0.0040 (12) | −0.0032 (13) |
| C4 | 0.0330 (17) | 0.0341 (18) | 0.0368 (18) | 0.0013 (14) | 0.0011 (13) | 0.0044 (14) |
| C5 | 0.0335 (17) | 0.0258 (17) | 0.0376 (17) | −0.0019 (13) | 0.0056 (13) | −0.0002 (13) |
| C6 | 0.0358 (17) | 0.0311 (18) | 0.0283 (16) | −0.0039 (14) | −0.0009 (13) | 0.0006 (13) |
| C7 | 0.0356 (18) | 0.0313 (18) | 0.0288 (16) | −0.0059 (14) | −0.0023 (13) | 0.0023 (13) |
| C8 | 0.0301 (16) | 0.0251 (16) | 0.0274 (16) | −0.0075 (13) | −0.0023 (12) | 0.0043 (12) |
| C9 | 0.0300 (16) | 0.0243 (16) | 0.0214 (14) | −0.0063 (13) | −0.0009 (11) | 0.0043 (12) |
| C10 | 0.052 (2) | 0.0295 (18) | 0.0191 (14) | 0.0013 (15) | −0.0020 (13) | −0.0031 (12) |
| C11 | 0.056 (2) | 0.0253 (17) | 0.0296 (17) | 0.0130 (15) | −0.0001 (15) | −0.0038 (13) |
| C12 | 0.0373 (17) | 0.0239 (16) | 0.0227 (15) | 0.0020 (13) | −0.0023 (12) | 0.0057 (12) |
| C13 | 0.051 (2) | 0.0319 (18) | 0.0185 (15) | 0.0053 (15) | −0.0046 (13) | −0.0041 (12) |
| C14 | 0.0457 (19) | 0.0232 (16) | 0.0299 (16) | 0.0090 (14) | −0.0031 (13) | −0.0029 (13) |
| Br1—C3 | 1.886 (3) | C4—C5 | 1.369 (4) |
| Cl1—C5 | 1.751 (3) | C4—H4 | 0.9300 |
| N1—C7 | 1.271 (4) | C5—C6 | 1.378 (4) |
| N1—N2 | 1.375 (3) | C6—H6 | 0.9300 |
| N2—C8 | 1.353 (4) | C7—H7 | 0.9300 |
| N2—H2 | 0.90 (3) | C8—C9 | 1.478 (4) |
| O1—C2 | 1.343 (3) | C9—C10 | 1.381 (4) |
| O1—H1 | 0.8200 | C9—C14 | 1.385 (4) |
| O2—C8 | 1.225 (3) | C10—C11 | 1.372 (4) |
| O3—C12 | 1.353 (3) | C10—H10 | 0.9300 |
| O3—H3 | 0.8200 | C11—C12 | 1.383 (4) |
| C1—C6 | 1.387 (4) | C11—H11 | 0.9300 |
| C1—C2 | 1.404 (4) | C12—C13 | 1.376 (4) |
| C1—C7 | 1.464 (4) | C13—C14 | 1.376 (4) |
| C2—C3 | 1.390 (4) | C13—H13 | 0.9300 |
| C3—C4 | 1.368 (4) | C14—H14 | 0.9300 |
| C7—N1—N2 | 117.2 (2) | N1—C7—C1 | 120.4 (3) |
| C8—N2—N1 | 119.4 (2) | N1—C7—H7 | 119.8 |
| C8—N2—H2 | 120 (3) | C1—C7—H7 | 119.8 |
| N1—N2—H2 | 120 (3) | O2—C8—N2 | 121.8 (3) |
| C2—O1—H1 | 109.5 | O2—C8—C9 | 121.4 (3) |
| C12—O3—H3 | 109.5 | N2—C8—C9 | 116.8 (2) |
| C6—C1—C2 | 119.3 (3) | C10—C9—C14 | 118.0 (3) |
| C6—C1—C7 | 119.1 (3) | C10—C9—C8 | 117.7 (2) |
| C2—C1—C7 | 121.6 (3) | C14—C9—C8 | 124.3 (3) |
| O1—C2—C3 | 118.4 (3) | C11—C10—C9 | 121.6 (3) |
| O1—C2—C1 | 123.2 (3) | C11—C10—H10 | 119.2 |
| C3—C2—C1 | 118.4 (3) | C9—C10—H10 | 119.2 |
| C4—C3—C2 | 122.0 (3) | C10—C11—C12 | 119.5 (3) |
| C4—C3—Br1 | 120.1 (2) | C10—C11—H11 | 120.2 |
| C2—C3—Br1 | 117.9 (2) | C12—C11—H11 | 120.2 |
| C3—C4—C5 | 119.0 (3) | O3—C12—C13 | 122.0 (3) |
| C3—C4—H4 | 120.5 | O3—C12—C11 | 118.2 (3) |
| C5—C4—H4 | 120.5 | C13—C12—C11 | 119.8 (3) |
| C4—C5—C6 | 121.2 (3) | C14—C13—C12 | 120.0 (3) |
| C4—C5—Cl1 | 119.1 (2) | C14—C13—H13 | 120.0 |
| C6—C5—Cl1 | 119.7 (2) | C12—C13—H13 | 120.0 |
| C5—C6—C1 | 120.2 (3) | C13—C14—C9 | 121.0 (3) |
| C5—C6—H6 | 119.9 | C13—C14—H14 | 119.5 |
| C1—C6—H6 | 119.9 | C9—C14—H14 | 119.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O3i | 0.90 (3) | 2.17 (3) | 2.922 (3) | 140 (3) |
| O1—H1···N1 | 0.82 | 1.91 | 2.623 (3) | 146. |
| Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O3i | 0.90 (3) | 2.17 (3) | 2.922 (3) | 140 (3) |
| O1—H1···N1 | 0.82 | 1.91 | 2.623 (3) | 146. |
| Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2. |
We thank the Top-Class Foundation and the Applied Chemistry Key Laboratory Foundation of Pingdingshan University.
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Schiff bases are a kind of versatile compounds, which possess excellent biological properties (Bhandari et al., 2008; Sinha et al., 2008; Sondhi et al., 2006; Singh et al., 2006). Recently, a large number of Schiff bases derived from the reaction of aldehydes with benzohydrazides have been reported (He & Liu, 2005; Zhen & Han, 2005; Diao & Yu, 2006; Shan et al., 2008; Fun et al., 2008). In this paper, a new Schiff base, (I), Fig. 1, derived from the reaction of 3-bromo-5-chlorosalicylaldehyde with 4-hydroxybenzohydrazide is reported. The title Schiff base is a planar-shaped compound, with mean deviation from the least-squares plane of 0.064 (3)Å, and with the dihedral angle between the C1-C6 and C9-C14 phenyl rings of 3.0 (2)°. All the bond lengths are comparable to the values in the similar Schiff bases (Jing et al., 2005; Lu et al., 2008; Salhin et al., 2007). There is a intramolecular O—H···N hydrogen bond (Fig. 1). In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds , to form a 3-D network (Table 1) (Fig. 2).