Acta Cryst. (2009). E65, o2415 [ doi:10.1107/S1600536809035740 ]
The title compound, C14H10ClN3O4, was synthesized by the reaction of 5-hydroxy-2-nitrobenzaldehyde with an equimolar quantity of 4-chlorobenzohydrazide in methanol. The molecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 3.9 (2)°. In the crystal structure, molecules are linked through intermolecular N-H
O and O-HO hydrogen bonds, forming chains running along the b axis.
The compound was prepared by refluxing equimolar quantities of 5-hydroxy-2-nitrobenzaldehyde with 4-chlorobenzohydrazide in methanol. Colorless block-like crystals were formed by slow evaporation of the solution in air.
H2 was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) 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, 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]](./om2273fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with ellipsoids drawn at the 30% probability level. |
![[Figure 2]](./om2273fig2thm.gif)
| Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are drawn as dashed lines. |
| C14H10ClN3O4 | Z = 2 |
| Mr = 319.70 | F(000) = 328 |
| Triclinic, P1 | Dx = 1.548 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.5386 (2) Å | Cell parameters from 2079 reflections |
| b = 8.1677 (2) Å | θ = 2.6–30.1° |
| c = 12.3435 (4) Å | µ = 0.30 mm−1 |
| α = 90.820 (3)° | T = 298 K |
| β = 106.056 (2)° | Block, colorless |
| γ = 109.014 (2)° | 0.23 × 0.20 × 0.20 mm |
| V = 685.95 (4) Å3 |
| Bruker SMART 1K diffractometer | 2933 independent reflections |
| Radiation source: fine-focus sealed tube | 2444 reflections with I > 2σ(I) |
| graphite | Rint = 0.013 |
| ω scans | θmax = 27.0°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→9 |
| Tmin = 0.934, Tmax = 0.942 | k = −10→10 |
| 4267 measured reflections | l = −15→15 |
| 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.2581P] where P = (Fo2 + 2Fc2)/3 |
| 2933 reflections | (Δ/σ)max = 0.001 |
| 203 parameters | Δρmax = 0.31 e Å−3 |
| 1 restraint | Δρmin = −0.37 e Å−3 |
| C14H10ClN3O4 | γ = 109.014 (2)° |
| Mr = 319.70 | V = 685.95 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.5386 (2) Å | Mo Kα radiation |
| b = 8.1677 (2) Å | µ = 0.30 mm−1 |
| c = 12.3435 (4) Å | T = 298 K |
| α = 90.820 (3)° | 0.23 × 0.20 × 0.20 mm |
| β = 106.056 (2)° |
| Bruker SMART 1K diffractometer | 2933 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2444 reflections with I > 2σ(I) |
| Tmin = 0.934, Tmax = 0.942 | Rint = 0.013 |
| 4267 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.112 | Δρmax = 0.31 e Å−3 |
| S = 1.04 | Δρmin = −0.37 e Å−3 |
| 2933 reflections | Absolute structure: ? |
| 203 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 | ||
| Cl1 | 1.99310 (8) | 1.22131 (10) | 1.02766 (6) | 0.0873 (3) | |
| N1 | 0.89654 (18) | 0.85347 (17) | 0.58743 (11) | 0.0363 (3) | |
| N2 | 1.08279 (18) | 0.88906 (18) | 0.65933 (12) | 0.0365 (3) | |
| N3 | 0.6482 (2) | 0.46355 (18) | 0.30087 (13) | 0.0424 (3) | |
| O1 | 0.7870 (2) | 0.43682 (18) | 0.36768 (12) | 0.0570 (4) | |
| O2 | 0.5932 (3) | 0.4105 (2) | 0.20048 (13) | 0.0756 (5) | |
| O3 | 0.22232 (17) | 0.82467 (17) | 0.43739 (11) | 0.0489 (3) | |
| H3 | 0.1313 | 0.8286 | 0.3839 | 0.073* | |
| O4 | 1.08646 (17) | 1.14913 (16) | 0.72801 (11) | 0.0458 (3) | |
| C1 | 0.6246 (2) | 0.67228 (19) | 0.44254 (13) | 0.0299 (3) | |
| C2 | 0.5411 (2) | 0.55749 (19) | 0.34209 (13) | 0.0332 (3) | |
| C3 | 0.3510 (2) | 0.5302 (2) | 0.27424 (14) | 0.0407 (4) | |
| H3A | 0.2995 | 0.4535 | 0.2079 | 0.049* | |
| C4 | 0.2379 (2) | 0.6149 (2) | 0.30395 (15) | 0.0407 (4) | |
| H4 | 0.1098 | 0.5944 | 0.2590 | 0.049* | |
| C5 | 0.3180 (2) | 0.7317 (2) | 0.40214 (14) | 0.0352 (3) | |
| C6 | 0.5077 (2) | 0.75750 (19) | 0.46992 (13) | 0.0322 (3) | |
| H6 | 0.5584 | 0.8346 | 0.5361 | 0.039* | |
| C7 | 0.8272 (2) | 0.7162 (2) | 0.51835 (13) | 0.0326 (3) | |
| H7 | 0.9012 | 0.6456 | 0.5154 | 0.039* | |
| C8 | 1.1687 (2) | 1.0418 (2) | 0.72753 (13) | 0.0337 (3) | |
| C9 | 1.3720 (2) | 1.0754 (2) | 0.80277 (13) | 0.0335 (3) | |
| C10 | 1.4371 (3) | 1.1911 (2) | 0.90032 (14) | 0.0438 (4) | |
| H10 | 1.3523 | 1.2403 | 0.9185 | 0.053* | |
| C11 | 1.6278 (3) | 1.2339 (3) | 0.97075 (15) | 0.0511 (5) | |
| H11 | 1.6716 | 1.3107 | 1.0366 | 0.061* | |
| C12 | 1.7510 (3) | 1.1612 (3) | 0.94169 (15) | 0.0474 (4) | |
| C13 | 1.6913 (2) | 1.0459 (2) | 0.84568 (15) | 0.0437 (4) | |
| H13 | 1.7774 | 0.9981 | 0.8278 | 0.052* | |
| C14 | 1.5000 (2) | 1.0026 (2) | 0.77637 (14) | 0.0362 (3) | |
| H14 | 1.4565 | 0.9239 | 0.7115 | 0.043* | |
| H2 | 1.141 (3) | 0.809 (2) | 0.660 (2) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0458 (3) | 0.1068 (5) | 0.0802 (4) | 0.0259 (3) | −0.0248 (3) | −0.0205 (4) |
| N1 | 0.0269 (6) | 0.0390 (7) | 0.0413 (7) | 0.0161 (5) | 0.0021 (5) | −0.0002 (6) |
| N2 | 0.0270 (6) | 0.0385 (7) | 0.0425 (7) | 0.0179 (5) | 0.0005 (5) | −0.0022 (6) |
| N3 | 0.0471 (8) | 0.0356 (7) | 0.0476 (8) | 0.0178 (6) | 0.0149 (7) | −0.0033 (6) |
| O1 | 0.0527 (8) | 0.0596 (8) | 0.0656 (9) | 0.0360 (7) | 0.0091 (7) | −0.0089 (7) |
| O2 | 0.0986 (13) | 0.0879 (11) | 0.0505 (9) | 0.0534 (10) | 0.0138 (8) | −0.0181 (8) |
| O3 | 0.0364 (6) | 0.0568 (8) | 0.0598 (8) | 0.0295 (6) | 0.0082 (6) | 0.0016 (6) |
| O4 | 0.0368 (6) | 0.0450 (7) | 0.0554 (7) | 0.0237 (5) | 0.0024 (5) | −0.0080 (5) |
| C1 | 0.0283 (7) | 0.0294 (7) | 0.0337 (7) | 0.0125 (6) | 0.0087 (6) | 0.0057 (6) |
| C2 | 0.0349 (8) | 0.0296 (7) | 0.0366 (8) | 0.0133 (6) | 0.0100 (6) | 0.0028 (6) |
| C3 | 0.0387 (9) | 0.0365 (8) | 0.0385 (9) | 0.0094 (7) | 0.0029 (7) | −0.0023 (7) |
| C4 | 0.0280 (7) | 0.0411 (9) | 0.0454 (9) | 0.0100 (7) | 0.0014 (7) | 0.0048 (7) |
| C5 | 0.0293 (7) | 0.0343 (8) | 0.0452 (9) | 0.0151 (6) | 0.0110 (6) | 0.0093 (7) |
| C6 | 0.0297 (7) | 0.0334 (7) | 0.0345 (8) | 0.0140 (6) | 0.0074 (6) | 0.0015 (6) |
| C7 | 0.0290 (7) | 0.0356 (8) | 0.0371 (8) | 0.0178 (6) | 0.0081 (6) | 0.0030 (6) |
| C8 | 0.0296 (7) | 0.0394 (8) | 0.0344 (8) | 0.0159 (6) | 0.0080 (6) | 0.0024 (6) |
| C9 | 0.0294 (7) | 0.0370 (8) | 0.0330 (8) | 0.0126 (6) | 0.0060 (6) | 0.0035 (6) |
| C10 | 0.0402 (9) | 0.0535 (10) | 0.0380 (9) | 0.0191 (8) | 0.0088 (7) | −0.0043 (7) |
| C11 | 0.0483 (10) | 0.0603 (11) | 0.0339 (9) | 0.0147 (9) | 0.0008 (8) | −0.0090 (8) |
| C12 | 0.0338 (8) | 0.0557 (11) | 0.0412 (9) | 0.0133 (8) | −0.0040 (7) | 0.0026 (8) |
| C13 | 0.0320 (8) | 0.0511 (10) | 0.0471 (10) | 0.0187 (7) | 0.0053 (7) | 0.0038 (8) |
| C14 | 0.0320 (8) | 0.0390 (8) | 0.0360 (8) | 0.0145 (6) | 0.0050 (6) | −0.0011 (6) |
| Cl1—C12 | 1.7399 (17) | C4—C5 | 1.389 (2) |
| N1—C7 | 1.266 (2) | C4—H4 | 0.9300 |
| N1—N2 | 1.3714 (17) | C5—C6 | 1.388 (2) |
| N2—C8 | 1.351 (2) | C6—H6 | 0.9300 |
| N2—H2 | 0.896 (10) | C7—H7 | 0.9300 |
| N3—O2 | 1.2160 (19) | C8—C9 | 1.489 (2) |
| N3—O1 | 1.2245 (19) | C9—C10 | 1.387 (2) |
| N3—C2 | 1.456 (2) | C9—C14 | 1.390 (2) |
| O3—C5 | 1.3447 (19) | C10—C11 | 1.385 (2) |
| O3—H3 | 0.8200 | C10—H10 | 0.9300 |
| O4—C8 | 1.2285 (18) | C11—C12 | 1.372 (3) |
| C1—C6 | 1.391 (2) | C11—H11 | 0.9300 |
| C1—C2 | 1.401 (2) | C12—C13 | 1.375 (3) |
| C1—C7 | 1.476 (2) | C13—C14 | 1.383 (2) |
| C2—C3 | 1.388 (2) | C13—H13 | 0.9300 |
| C3—C4 | 1.375 (2) | C14—H14 | 0.9300 |
| C3—H3A | 0.9300 | ||
| C7—N1—N2 | 116.59 (12) | C1—C6—H6 | 118.8 |
| C8—N2—N1 | 118.41 (12) | N1—C7—C1 | 117.56 (13) |
| C8—N2—H2 | 122.9 (16) | N1—C7—H7 | 121.2 |
| N1—N2—H2 | 118.7 (16) | C1—C7—H7 | 121.2 |
| O2—N3—O1 | 121.99 (15) | O4—C8—N2 | 122.68 (14) |
| O2—N3—C2 | 118.32 (15) | O4—C8—C9 | 120.98 (14) |
| O1—N3—C2 | 119.67 (14) | N2—C8—C9 | 116.33 (13) |
| C5—O3—H3 | 109.5 | C10—C9—C14 | 119.36 (14) |
| C6—C1—C2 | 116.51 (13) | C10—C9—C8 | 117.71 (14) |
| C6—C1—C7 | 117.54 (13) | C14—C9—C8 | 122.85 (14) |
| C2—C1—C7 | 125.89 (13) | C11—C10—C9 | 120.34 (16) |
| C3—C2—C1 | 121.43 (14) | C11—C10—H10 | 119.8 |
| C3—C2—N3 | 115.96 (14) | C9—C10—H10 | 119.8 |
| C1—C2—N3 | 122.59 (14) | C12—C11—C10 | 118.85 (16) |
| C4—C3—C2 | 120.83 (15) | C12—C11—H11 | 120.6 |
| C4—C3—H3A | 119.6 | C10—C11—H11 | 120.6 |
| C2—C3—H3A | 119.6 | C11—C12—C13 | 122.33 (16) |
| C3—C4—C5 | 119.00 (14) | C11—C12—Cl1 | 118.73 (14) |
| C3—C4—H4 | 120.5 | C13—C12—Cl1 | 118.92 (15) |
| C5—C4—H4 | 120.5 | C12—C13—C14 | 118.43 (16) |
| O3—C5—C6 | 116.31 (14) | C12—C13—H13 | 120.8 |
| O3—C5—C4 | 123.86 (14) | C14—C13—H13 | 120.8 |
| C6—C5—C4 | 119.83 (14) | C13—C14—C9 | 120.67 (15) |
| C5—C6—C1 | 122.38 (14) | C13—C14—H14 | 119.7 |
| C5—C6—H6 | 118.8 | C9—C14—H14 | 119.7 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O4i | 0.82 | 1.89 | 2.7093 (17) | 174 |
| N2—H2···O1ii | 0.90 (1) | 2.29 (1) | 3.1649 (18) | 165 (2) |
| Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O4i | 0.82 | 1.89 | 2.7093 (17) | 174 |
| N2—H2···O1ii | 0.90 (1) | 2.29 (1) | 3.1649 (18) | 165 (2) |
| Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1. |
The Vital Foundation of Ankang University (project No. 2008AKXY012) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02 J K202) are gratefully acknowledged.
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In the last few years, the crystal structures of a large number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008; Cao & Lu, 2009a,b), the title new hydrazone compound, derived from the reaction of 5-hydroxy-2-nitrobenzaldehyde with an equimolar quantity of 4-chlorobenzohydrazide, is reported.
In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 3.9 (2)°. The molecule displays an E configuration about the C═N bond. In the crystal structure, molecules are linked through intermolecular N—H···O and O—H···O hydrogen bonds, Table 1, to form chains running along the b axis, Fig. 2.