Acta Cryst. (2008). E64, o1383 [ doi:10.1107/S1600536808019636 ]
In the title compound, C14H10ClN3O4·CH3OH, the dihedral angle between the two benzene rings is 33.9 (2)°. In the crystal structure, the methanol solvent molecules are linked to the Schiff base molecules through intermolecular N-H
O and O-HO hydrogen bonds. Molecules are further linked through intermolecular O-HO and O-HN hydrogen bonds, forming chains running along the b axis.
2-Chloro-5-nitrobenzaldehyde (1.0 mmol, 167.1 mg) and 3-hydroxybenzohydrazide (1.0 mmol, 152.1 mg) were dissolved in methanol (30 ml). The mixture was stirred at reflux for 30 min to give a colourless solution. After keeping the solution in air for a few days, colourless block-shaped crystals were formed.
H3B was located in a difference Fourier map and refined isotropically, with Uiso(H) fixed at 0.08 Å2. Other H atoms were positioned geometrically and refined using a riding model with O–H = 0.92 Å, C–H = 0.93-0.96 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C, 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]](./rz2226fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Hydrogen bond is shown as a dashed line. |
![[Figure 2]](./rz2226fig2thm.gif)
| Fig. 2. The crystal packing of the title copound, viewed along the a axis. Hydrogen bonds are shown as dashed lines. |
| C14H10ClN3O4·CH4O | F000 = 728 |
| Mr = 351.74 | Dx = 1.458 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2947 reflections |
| a = 7.716 (3) Å | θ = 2.3–24.5º |
| b = 11.945 (2) Å | µ = 0.27 mm−1 |
| c = 17.650 (3) Å | T = 298 (2) K |
| β = 99.886 (2)º | Block, colourless |
| V = 1602.6 (7) Å3 | 0.27 × 0.23 × 0.22 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 3316 independent reflections |
| Radiation source: fine-focus sealed tube | 2396 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.034 |
| T = 298(2) K | θmax = 26.5º |
| ω scans | θmin = 2.1º |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→9 |
| Tmin = 0.931, Tmax = 0.943 | k = −14→14 |
| 12656 measured reflections | l = −21→22 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0596P)2 + 0.2859P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max < 0.001 |
| 3316 reflections | Δρmax = 0.18 e Å−3 |
| 223 parameters | Δρmin = −0.22 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C14H10ClN3O4·CH4O | V = 1602.6 (7) Å3 |
| Mr = 351.74 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 7.716 (3) Å | µ = 0.27 mm−1 |
| b = 11.945 (2) Å | T = 298 (2) K |
| c = 17.650 (3) Å | 0.27 × 0.23 × 0.22 mm |
| β = 99.886 (2)º |
| Bruker SMART CCD area-detector diffractometer | 3316 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2396 reflections with I > 2σ(I) |
| Tmin = 0.931, Tmax = 0.943 | Rint = 0.034 |
| 12656 measured reflections |
| R[F2 > 2σ(F2)] = 0.045 | 223 parameters |
| wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.01 | Δρmax = 0.18 e Å−3 |
| 3316 reflections | Δρmin = −0.22 e Å−3 |
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. |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.27705 (9) | 0.68944 (5) | 0.42450 (4) | 0.0774 (2) | |
| O1 | −0.1188 (3) | 1.16001 (18) | 0.30340 (10) | 0.0978 (7) | |
| O2 | 0.0033 (3) | 1.21390 (16) | 0.41618 (12) | 0.0859 (6) | |
| O3 | 0.4707 (2) | 1.09327 (11) | 0.70885 (8) | 0.0623 (4) | |
| O4 | 0.6995 (2) | 0.71117 (11) | 0.91382 (8) | 0.0607 (4) | |
| H4 | 0.6479 | 0.6690 | 0.8808 | 0.091* | |
| O5 | 0.6192 (3) | 0.69826 (13) | 0.66034 (11) | 0.0897 (6) | |
| H5 | 0.5907 | 0.6645 | 0.6968 | 0.135* | |
| N1 | −0.0240 (3) | 1.14400 (19) | 0.36561 (12) | 0.0652 (5) | |
| N2 | 0.3857 (2) | 0.95587 (12) | 0.58923 (8) | 0.0428 (4) | |
| N3 | 0.4964 (2) | 0.92397 (13) | 0.65533 (9) | 0.0424 (4) | |
| C1 | 0.2405 (2) | 0.90699 (16) | 0.46380 (10) | 0.0439 (5) | |
| C2 | 0.1934 (3) | 0.82357 (18) | 0.40857 (12) | 0.0534 (5) | |
| C3 | 0.0788 (3) | 0.8448 (2) | 0.34054 (13) | 0.0684 (7) | |
| H3 | 0.0502 | 0.7880 | 0.3045 | 0.082* | |
| C4 | 0.0082 (3) | 0.9485 (2) | 0.32639 (12) | 0.0663 (7) | |
| H4A | −0.0690 | 0.9633 | 0.2810 | 0.080* | |
| C5 | 0.0531 (3) | 1.03136 (19) | 0.38052 (11) | 0.0533 (5) | |
| C6 | 0.1661 (3) | 1.01296 (17) | 0.44857 (10) | 0.0468 (5) | |
| H6 | 0.1927 | 1.0705 | 0.4841 | 0.056* | |
| C7 | 0.3601 (3) | 0.88397 (16) | 0.53602 (11) | 0.0460 (5) | |
| H7 | 0.4179 | 0.8154 | 0.5428 | 0.055* | |
| C8 | 0.5280 (2) | 0.99647 (15) | 0.71415 (10) | 0.0429 (4) | |
| C9 | 0.6354 (2) | 0.95567 (15) | 0.78653 (10) | 0.0409 (4) | |
| C10 | 0.6158 (2) | 0.84831 (15) | 0.81342 (10) | 0.0414 (4) | |
| H10 | 0.5366 | 0.7992 | 0.7849 | 0.050* | |
| C11 | 0.7141 (3) | 0.81385 (16) | 0.88285 (11) | 0.0451 (5) | |
| C12 | 0.8325 (3) | 0.88781 (18) | 0.92424 (11) | 0.0536 (5) | |
| H12 | 0.9003 | 0.8652 | 0.9704 | 0.064* | |
| C13 | 0.8499 (3) | 0.99430 (19) | 0.89738 (12) | 0.0591 (6) | |
| H13 | 0.9295 | 1.0432 | 0.9259 | 0.071* | |
| C14 | 0.7518 (3) | 1.03021 (17) | 0.82898 (11) | 0.0511 (5) | |
| H14 | 0.7633 | 1.1029 | 0.8116 | 0.061* | |
| C15 | 0.6536 (4) | 0.6218 (2) | 0.60542 (17) | 0.0899 (9) | |
| H15A | 0.6769 | 0.6613 | 0.5609 | 0.135* | |
| H15B | 0.5535 | 0.5739 | 0.5911 | 0.135* | |
| H15C | 0.7542 | 0.5775 | 0.6263 | 0.135* | |
| H3B | 0.538 (3) | 0.862 (2) | 0.6593 (14) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0721 (4) | 0.0661 (4) | 0.0918 (5) | 0.0006 (3) | 0.0077 (3) | −0.0362 (3) |
| O1 | 0.1037 (15) | 0.1191 (16) | 0.0612 (11) | 0.0065 (12) | −0.0124 (10) | 0.0357 (11) |
| O2 | 0.0977 (14) | 0.0643 (11) | 0.0857 (13) | 0.0020 (10) | −0.0123 (11) | 0.0069 (10) |
| O3 | 0.0989 (12) | 0.0348 (8) | 0.0464 (8) | 0.0086 (7) | −0.0068 (8) | −0.0028 (6) |
| O4 | 0.0881 (12) | 0.0414 (8) | 0.0441 (8) | −0.0011 (7) | −0.0130 (7) | 0.0061 (6) |
| O5 | 0.1570 (19) | 0.0489 (10) | 0.0750 (12) | 0.0195 (10) | 0.0527 (12) | 0.0041 (8) |
| N1 | 0.0607 (12) | 0.0783 (14) | 0.0543 (12) | −0.0043 (10) | 0.0038 (10) | 0.0231 (11) |
| N2 | 0.0519 (10) | 0.0387 (8) | 0.0355 (8) | −0.0009 (7) | 0.0013 (7) | −0.0009 (7) |
| N3 | 0.0523 (10) | 0.0363 (8) | 0.0357 (8) | 0.0010 (7) | −0.0005 (7) | −0.0004 (7) |
| C1 | 0.0437 (11) | 0.0531 (12) | 0.0356 (10) | −0.0079 (8) | 0.0087 (8) | −0.0059 (8) |
| C2 | 0.0507 (12) | 0.0624 (13) | 0.0489 (12) | −0.0078 (10) | 0.0132 (10) | −0.0157 (10) |
| C3 | 0.0644 (15) | 0.0928 (19) | 0.0463 (13) | −0.0128 (14) | 0.0050 (11) | −0.0305 (13) |
| C4 | 0.0610 (14) | 0.097 (2) | 0.0378 (11) | −0.0051 (13) | 0.0000 (10) | −0.0035 (12) |
| C5 | 0.0506 (12) | 0.0699 (14) | 0.0396 (11) | −0.0102 (10) | 0.0080 (9) | 0.0053 (10) |
| C6 | 0.0508 (11) | 0.0549 (12) | 0.0343 (10) | −0.0117 (9) | 0.0061 (8) | −0.0001 (8) |
| C7 | 0.0541 (12) | 0.0415 (10) | 0.0413 (10) | −0.0005 (9) | 0.0054 (9) | −0.0035 (8) |
| C8 | 0.0526 (11) | 0.0343 (10) | 0.0403 (10) | −0.0041 (8) | 0.0041 (9) | −0.0002 (8) |
| C9 | 0.0476 (11) | 0.0382 (10) | 0.0359 (9) | −0.0012 (8) | 0.0041 (8) | −0.0030 (7) |
| C10 | 0.0477 (11) | 0.0377 (10) | 0.0359 (10) | −0.0013 (8) | −0.0012 (8) | −0.0065 (8) |
| C11 | 0.0540 (12) | 0.0415 (11) | 0.0376 (10) | 0.0039 (8) | 0.0020 (9) | −0.0016 (8) |
| C12 | 0.0553 (13) | 0.0621 (13) | 0.0379 (10) | −0.0032 (10) | −0.0075 (9) | −0.0019 (9) |
| C13 | 0.0626 (14) | 0.0634 (14) | 0.0462 (12) | −0.0232 (11) | −0.0049 (10) | −0.0094 (10) |
| C14 | 0.0627 (13) | 0.0434 (11) | 0.0449 (11) | −0.0141 (9) | 0.0026 (10) | −0.0020 (9) |
| C15 | 0.109 (2) | 0.0755 (18) | 0.095 (2) | 0.0083 (16) | 0.0456 (18) | −0.0195 (16) |
| Cl1—C2 | 1.732 (2) | C4—C5 | 1.378 (3) |
| O1—N1 | 1.225 (2) | C4—H4A | 0.9300 |
| O2—N1 | 1.214 (3) | C5—C6 | 1.375 (3) |
| O3—C8 | 1.236 (2) | C6—H6 | 0.9300 |
| O4—C11 | 1.355 (2) | C7—H7 | 0.9300 |
| O4—H4 | 0.8200 | C8—C9 | 1.481 (2) |
| O5—C15 | 1.390 (3) | C9—C10 | 1.385 (3) |
| O5—H5 | 0.8200 | C9—C14 | 1.389 (3) |
| N1—C5 | 1.477 (3) | C10—C11 | 1.388 (3) |
| N2—C7 | 1.263 (2) | C10—H10 | 0.9300 |
| N2—N3 | 1.376 (2) | C11—C12 | 1.385 (3) |
| N3—C8 | 1.342 (2) | C12—C13 | 1.372 (3) |
| N3—H3B | 0.81 (3) | C12—H12 | 0.9300 |
| C1—C6 | 1.397 (3) | C13—C14 | 1.379 (3) |
| C1—C2 | 1.398 (3) | C13—H13 | 0.9300 |
| C1—C7 | 1.466 (3) | C14—H14 | 0.9300 |
| C2—C3 | 1.387 (3) | C15—H15A | 0.9600 |
| C3—C4 | 1.358 (4) | C15—H15B | 0.9600 |
| C3—H3 | 0.9300 | C15—H15C | 0.9600 |
| C11—O4—H4 | 109.5 | C1—C7—H7 | 119.5 |
| C15—O5—H5 | 109.5 | O3—C8—N3 | 122.02 (17) |
| O2—N1—O1 | 123.6 (2) | O3—C8—C9 | 120.89 (16) |
| O2—N1—C5 | 118.83 (18) | N3—C8—C9 | 117.09 (16) |
| O1—N1—C5 | 117.5 (2) | C10—C9—C14 | 120.50 (17) |
| C7—N2—N3 | 115.93 (16) | C10—C9—C8 | 121.50 (16) |
| C8—N3—N2 | 118.75 (15) | C14—C9—C8 | 117.94 (17) |
| C8—N3—H3B | 120.6 (18) | C9—C10—C11 | 120.11 (17) |
| N2—N3—H3B | 120.6 (18) | C9—C10—H10 | 119.9 |
| C6—C1—C2 | 117.57 (18) | C11—C10—H10 | 119.9 |
| C6—C1—C7 | 120.92 (17) | O4—C11—C12 | 117.23 (17) |
| C2—C1—C7 | 121.49 (18) | O4—C11—C10 | 123.60 (17) |
| C3—C2—C1 | 121.6 (2) | C12—C11—C10 | 119.16 (18) |
| C3—C2—Cl1 | 118.32 (17) | C13—C12—C11 | 120.26 (18) |
| C1—C2—Cl1 | 120.09 (16) | C13—C12—H12 | 119.9 |
| C4—C3—C2 | 120.1 (2) | C11—C12—H12 | 119.9 |
| C4—C3—H3 | 119.9 | C12—C13—C14 | 121.29 (18) |
| C2—C3—H3 | 119.9 | C12—C13—H13 | 119.4 |
| C3—C4—C5 | 118.8 (2) | C14—C13—H13 | 119.4 |
| C3—C4—H4A | 120.6 | C13—C14—C9 | 118.66 (19) |
| C5—C4—H4A | 120.6 | C13—C14—H14 | 120.7 |
| C6—C5—C4 | 122.5 (2) | C9—C14—H14 | 120.7 |
| C6—C5—N1 | 118.48 (19) | O5—C15—H15A | 109.5 |
| C4—C5—N1 | 119.0 (2) | O5—C15—H15B | 109.5 |
| C5—C6—C1 | 119.39 (19) | H15A—C15—H15B | 109.5 |
| C5—C6—H6 | 120.3 | O5—C15—H15C | 109.5 |
| C1—C6—H6 | 120.3 | H15A—C15—H15C | 109.5 |
| N2—C7—C1 | 120.94 (18) | H15B—C15—H15C | 109.5 |
| N2—C7—H7 | 119.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O4—H4···O3i | 0.82 | 1.91 | 2.7237 (19) | 169 |
| O4—H4···N2i | 0.82 | 2.62 | 3.118 (2) | 120 |
| O5—H5···O3i | 0.82 | 2.00 | 2.817 (2) | 175 |
| N3—H3B···O5 | 0.81 (3) | 2.05 (3) | 2.854 (2) | 173 (3) |
| Symmetry codes: (i) −x+1, y−1/2, −z+3/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O4—H4···O3i | 0.82 | 1.91 | 2.7237 (19) | 169 |
| O4—H4···N2i | 0.82 | 2.62 | 3.118 (2) | 120 |
| O5—H5···O3i | 0.82 | 2.00 | 2.817 (2) | 175 |
| N3—H3B···O5 | 0.81 (3) | 2.05 (3) | 2.854 (2) | 173 (3) |
| Symmetry codes: (i) −x+1, y−1/2, −z+3/2. |
Ali, H. M., Zuraini, K., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1729–o1730.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Jasinski, J. P., Narayana, B., Sunil, K. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3652.
He, L. (2008). Acta Cryst. E64, o82.
Jing, Z.-L. & Yu, M. (2007). Acta Cryst. E63, o509–o510.
Nie, Y. (2008). Acta Cryst. E64, o471.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Zhou, Z. & Tang, R.-R. (2007). Acta Cryst. E63, m2960.
Zhou, Z. & Xiao, Z.-H. (2007). Acta Cryst. E63, m2012.
Recently, we have reported two metal complexes with Schiff base ligands (Zhou & Tang, 2007; Zhou & Xiao, 2007). We report herein the crystal structure of the title Schiff base compound (Fig. 1).
The title compound consists of a Schiff base molecule and a methanol molecule of crystallization. The dihedral angle between the two benzene rings is 33.9 (2)°. All bond lengths are comparable to those found in similar compounds (Ali et al., 2007; Nie, 2008; He, 2008; Butcher et al., 2007; Jing & Yu, 2007). In the crystal structure, the methanol molecules are linked to the Schiff base molecules through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1). Molecules are further linked through intermolecular O—H···O and O—H···N hydrogen bonds to form chains running along the b axis (Fig. 2).