Acta Cryst. (2008). E64, o2061 [ doi:10.1107/S1600536808030675 ]
The title compound, C14H10Br2N2O2, was synthesized by the reaction of 5-bromosalicylaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The dihedral angle between the two benzene rings is 10.5 (4)°. In the crystal structure, molecules are linked through intermolecular N-H
O hydrogen bonds to form chains parallel to the c axis, and an intramolecular O-HN interaction also occurs.
The compound was prepared by refluxing equimolar quantities of 5-bromosalicylaldehyde with 3-bromobenzohydrazide in methanol. Colorless block-like crystals were formed when the solution was evaporated in air for about a week.
H2 was located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (4) Å. 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, the O–H distance of 0.82 Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(O).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./bx2182fig1thm.gif)
| Fig. 1. The molecular structure of (I) with ellipsoids drawn at the 30% probability level. Dashed lines indicate intramolecular hydrogen bond. |
![[Figure 2]](./bx2182fig2thm.gif)
| Fig. 2. The molecular packing of (I), viewed along the a axis. Hydrogen bonds are drawn as dashed lines. |
| C14H10Br2N2O2 | F(000) = 776 |
| Mr = 398.06 | Dx = 1.858 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 5.657 (5) Å | Cell parameters from 1979 reflections |
| b = 32.08 (3) Å | θ = 2.5–25.3° |
| c = 7.856 (7) Å | µ = 5.70 mm−1 |
| β = 93.217 (13)° | T = 298 K |
| V = 1423 (2) Å3 | Block, colorless |
| Z = 4 | 0.13 × 0.08 × 0.07 mm |
| Bruker SMART CCD area-detector diffractometer | 3227 independent reflections |
| Radiation source: fine-focus sealed tube | 1830 reflections with I > 2σ(I) |
| graphite | Rint = 0.044 |
| ω scans | θmax = 27.5°, θmin = 2.5° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −7→5 |
| Tmin = 0.525, Tmax = 0.691 | k = −40→40 |
| 8526 measured reflections | l = −10→8 |
| 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0261P)2 + 2.1967P] where P = (Fo2 + 2Fc2)/3 |
| 3227 reflections | (Δ/σ)max = 0.001 |
| 185 parameters | Δρmax = 0.36 e Å−3 |
| 1 restraint | Δρmin = −0.62 e Å−3 |
| C14H10Br2N2O2 | V = 1423 (2) Å3 |
| Mr = 398.06 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 5.657 (5) Å | µ = 5.70 mm−1 |
| b = 32.08 (3) Å | T = 298 K |
| c = 7.856 (7) Å | 0.13 × 0.08 × 0.07 mm |
| β = 93.217 (13)° |
| Bruker SMART CCD area-detector diffractometer | 3227 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1830 reflections with I > 2σ(I) |
| Tmin = 0.525, Tmax = 0.691 | Rint = 0.044 |
| 8526 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.108 | Δρmax = 0.36 e Å−3 |
| S = 1.06 | Δρmin = −0.62 e Å−3 |
| 3227 reflections | Absolute structure: ? |
| 185 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 | 0.52024 (14) | 0.488709 (18) | 0.25097 (9) | 0.0871 (3) | |
| Br2 | 0.48529 (11) | 0.059801 (15) | 0.43970 (8) | 0.0683 (2) | |
| O1 | 0.9846 (6) | 0.33095 (11) | 0.5203 (5) | 0.0569 (9) | |
| H1 | 0.8927 | 0.3112 | 0.5117 | 0.085* | |
| O2 | 0.6434 (6) | 0.22201 (10) | 0.6015 (4) | 0.0607 (10) | |
| N1 | 0.5896 (7) | 0.29247 (11) | 0.4185 (5) | 0.0451 (9) | |
| N2 | 0.4480 (7) | 0.25766 (12) | 0.3888 (5) | 0.0482 (10) | |
| C1 | 0.6522 (8) | 0.36456 (14) | 0.3700 (5) | 0.0398 (10) | |
| C2 | 0.8762 (8) | 0.36571 (15) | 0.4560 (6) | 0.0455 (11) | |
| C3 | 0.9919 (10) | 0.40362 (17) | 0.4777 (7) | 0.0596 (14) | |
| H3 | 1.1409 | 0.4045 | 0.5339 | 0.072* | |
| C4 | 0.8888 (11) | 0.43984 (17) | 0.4170 (7) | 0.0655 (15) | |
| H4 | 0.9687 | 0.4650 | 0.4317 | 0.079* | |
| C5 | 0.6659 (10) | 0.43900 (15) | 0.3338 (6) | 0.0572 (13) | |
| C6 | 0.5510 (9) | 0.40199 (14) | 0.3089 (6) | 0.0485 (12) | |
| H6 | 0.4034 | 0.4015 | 0.2505 | 0.058* | |
| C7 | 0.5168 (8) | 0.32626 (14) | 0.3474 (6) | 0.0437 (11) | |
| H7 | 0.3758 | 0.3264 | 0.2806 | 0.052* | |
| C8 | 0.4901 (8) | 0.22345 (14) | 0.4857 (6) | 0.0431 (11) | |
| C9 | 0.3421 (8) | 0.18595 (14) | 0.4356 (5) | 0.0398 (10) | |
| C10 | 0.4437 (8) | 0.14749 (13) | 0.4676 (5) | 0.0419 (11) | |
| H10 | 0.5908 | 0.1456 | 0.5261 | 0.050* | |
| C11 | 0.3267 (9) | 0.11187 (14) | 0.4127 (6) | 0.0472 (12) | |
| C12 | 0.1049 (9) | 0.11408 (17) | 0.3310 (6) | 0.0568 (14) | |
| H12 | 0.0270 | 0.0899 | 0.2939 | 0.068* | |
| C13 | 0.0001 (9) | 0.15246 (17) | 0.3051 (6) | 0.0547 (13) | |
| H13 | −0.1513 | 0.1542 | 0.2530 | 0.066* | |
| C14 | 0.1181 (8) | 0.18839 (15) | 0.3557 (6) | 0.0471 (12) | |
| H14 | 0.0472 | 0.2142 | 0.3362 | 0.057* | |
| H2 | 0.339 (7) | 0.2580 (16) | 0.301 (5) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.1139 (6) | 0.0458 (3) | 0.1014 (5) | 0.0013 (3) | 0.0025 (4) | 0.0130 (3) |
| Br2 | 0.0836 (4) | 0.0420 (3) | 0.0786 (4) | −0.0039 (3) | −0.0013 (3) | 0.0049 (3) |
| O1 | 0.038 (2) | 0.064 (2) | 0.067 (2) | −0.0044 (17) | −0.0141 (17) | 0.0082 (19) |
| O2 | 0.068 (2) | 0.0479 (19) | 0.062 (2) | 0.0009 (17) | −0.0422 (19) | 0.0007 (16) |
| N1 | 0.049 (2) | 0.039 (2) | 0.045 (2) | −0.0038 (18) | −0.0151 (18) | −0.0009 (17) |
| N2 | 0.051 (3) | 0.040 (2) | 0.051 (2) | −0.0048 (19) | −0.027 (2) | 0.0026 (18) |
| C1 | 0.034 (3) | 0.050 (3) | 0.035 (2) | −0.002 (2) | 0.002 (2) | −0.006 (2) |
| C2 | 0.040 (3) | 0.052 (3) | 0.044 (3) | −0.007 (2) | 0.001 (2) | −0.001 (2) |
| C3 | 0.050 (3) | 0.069 (4) | 0.058 (3) | −0.013 (3) | −0.007 (3) | −0.010 (3) |
| C4 | 0.073 (4) | 0.057 (3) | 0.065 (4) | −0.027 (3) | 0.001 (3) | −0.006 (3) |
| C5 | 0.070 (4) | 0.047 (3) | 0.055 (3) | −0.007 (3) | 0.006 (3) | 0.002 (2) |
| C6 | 0.060 (3) | 0.046 (3) | 0.039 (3) | −0.002 (2) | −0.002 (2) | −0.001 (2) |
| C7 | 0.039 (3) | 0.052 (3) | 0.039 (3) | −0.003 (2) | −0.009 (2) | −0.002 (2) |
| C8 | 0.043 (3) | 0.043 (3) | 0.042 (3) | 0.004 (2) | −0.011 (2) | −0.001 (2) |
| C9 | 0.042 (3) | 0.049 (3) | 0.027 (2) | −0.002 (2) | −0.009 (2) | 0.0001 (19) |
| C10 | 0.039 (3) | 0.049 (3) | 0.037 (3) | 0.000 (2) | −0.007 (2) | 0.001 (2) |
| C11 | 0.057 (3) | 0.046 (3) | 0.039 (3) | −0.005 (2) | 0.003 (2) | −0.001 (2) |
| C12 | 0.053 (3) | 0.061 (3) | 0.056 (3) | −0.022 (3) | −0.002 (3) | −0.002 (3) |
| C13 | 0.039 (3) | 0.072 (4) | 0.052 (3) | −0.011 (3) | −0.008 (2) | −0.004 (3) |
| C14 | 0.038 (3) | 0.059 (3) | 0.043 (3) | 0.000 (2) | −0.001 (2) | 0.001 (2) |
| Br1—C5 | 1.893 (5) | C4—H4 | 0.9300 |
| Br2—C11 | 1.902 (5) | C5—C6 | 1.362 (6) |
| O1—C2 | 1.356 (5) | C6—H6 | 0.9300 |
| O1—H1 | 0.8200 | C7—H7 | 0.9300 |
| O2—C8 | 1.222 (5) | C8—C9 | 1.505 (6) |
| N1—C7 | 1.277 (5) | C9—C10 | 1.378 (6) |
| N1—N2 | 1.386 (5) | C9—C14 | 1.385 (6) |
| N2—C8 | 1.349 (6) | C10—C11 | 1.377 (6) |
| N2—H2 | 0.90 (4) | C10—H10 | 0.9300 |
| C1—C2 | 1.402 (6) | C11—C12 | 1.379 (7) |
| C1—C6 | 1.403 (6) | C12—C13 | 1.376 (7) |
| C1—C7 | 1.453 (6) | C12—H12 | 0.9300 |
| C2—C3 | 1.387 (6) | C13—C14 | 1.379 (6) |
| C3—C4 | 1.373 (7) | C13—H13 | 0.9300 |
| C3—H3 | 0.9300 | C14—H14 | 0.9300 |
| C4—C5 | 1.387 (7) | ||
| C2—O1—H1 | 109.5 | N1—C7—H7 | 119.7 |
| C7—N1—N2 | 116.2 (4) | C1—C7—H7 | 119.7 |
| C8—N2—N1 | 118.6 (3) | O2—C8—N2 | 123.1 (4) |
| C8—N2—H2 | 122 (4) | O2—C8—C9 | 121.7 (4) |
| N1—N2—H2 | 119 (4) | N2—C8—C9 | 115.1 (4) |
| C2—C1—C6 | 118.9 (4) | C10—C9—C14 | 119.7 (4) |
| C2—C1—C7 | 122.5 (4) | C10—C9—C8 | 116.6 (4) |
| C6—C1—C7 | 118.6 (4) | C14—C9—C8 | 123.7 (4) |
| O1—C2—C3 | 118.3 (4) | C11—C10—C9 | 119.8 (4) |
| O1—C2—C1 | 122.3 (4) | C11—C10—H10 | 120.1 |
| C3—C2—C1 | 119.3 (5) | C9—C10—H10 | 120.1 |
| C4—C3—C2 | 120.7 (5) | C10—C11—C12 | 120.8 (5) |
| C4—C3—H3 | 119.6 | C10—C11—Br2 | 118.6 (4) |
| C2—C3—H3 | 119.6 | C12—C11—Br2 | 120.6 (4) |
| C3—C4—C5 | 120.3 (5) | C13—C12—C11 | 119.2 (5) |
| C3—C4—H4 | 119.9 | C13—C12—H12 | 120.4 |
| C5—C4—H4 | 119.9 | C11—C12—H12 | 120.4 |
| C6—C5—C4 | 119.9 (5) | C12—C13—C14 | 120.5 (5) |
| C6—C5—Br1 | 119.3 (4) | C12—C13—H13 | 119.8 |
| C4—C5—Br1 | 120.8 (4) | C14—C13—H13 | 119.8 |
| C5—C6—C1 | 120.9 (5) | C13—C14—C9 | 119.9 (5) |
| C5—C6—H6 | 119.5 | C13—C14—H14 | 120.0 |
| C1—C6—H6 | 119.5 | C9—C14—H14 | 120.0 |
| N1—C7—C1 | 120.6 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 1.92 | 2.638 (5) | 145 |
| N2—H2···O2i | 0.90 (4) | 1.98 (2) | 2.838 (5) | 160 (5) |
| Symmetry codes: (i) x−1/2, −y+1/2, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 1.92 | 2.638 (5) | 145 |
| N2—H2···O2i | 0.90 (4) | 1.98 (2) | 2.838 (5) | 160 (5) |
| Symmetry codes: (i) x−1/2, −y+1/2, z−1/2. |
The Natural Scientific Research Foundation of the Education Office of Shanxi Province (project No. 07 J K177) is acknowledged.
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We have recently reported some transition metal complexes with Schiff base ligands (Cao, 2007a,b) and a hydrazone compound (Yang et al., 2008). We report herein the crystal structure of the title compound, (I), derived from the reaction of 5-bromosalicylaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol.
In compound (I), Fig. 1, the dihedral angle between the two benzene rings is 10.5 (4)°. All the bond values are comparable to those in other similar hydrazones (Zhen & Han, 2005; Peng & Hou, 2008; Tang, 2008; Salhin et al., 2007; Yathirajan et al., 2007). In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds, Table 1, to form chains parallel to the c axis, Fig. 2.