Abstract
The title compound, C21H15Cl2N2O3, displays a trans configuration with respect to the C=N double bond. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond.
Related literature
For related compounds, see: Salem (1998 ▶); Chang & Ji (2007 ▶).
Experimental
Crystal data
C21H15Cl2N2O3
M r = 414.25
Triclinic,
a = 8.9814 (9) Å
b = 10.8867 (11) Å
c = 11.5291 (13) Å
α = 89.623 (2)°
β = 72.700 (1)°
γ = 66.947 (2)°
V = 982.57 (18) Å3
Z = 2
Mo Kα radiation
μ = 0.36 mm−1
T = 273 (2) K
0.18 × 0.15 × 0.10 mm
Data collection
Bruker APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.949, T max = 0.965
5254 measured reflections
3459 independent reflections
2262 reflections with I > 2σ(I)
R int = 0.016
Refinement
R[F 2 > 2σ(F 2)] = 0.054
wR(F 2) = 0.207
S = 1.00
3459 reflections
255 parameters
H-atom parameters constrained
Δρmax = 0.41 e Å−3
Δρmin = −0.29 e Å−3
Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064069/gd2026sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064069/gd2026Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1—H1⋯N2 | 0.82 | 1.82 | 2.528 (3) | 145 |
Acknowledgments
This project was supported by the Postgraduate Foundation of Taishan University (No. Y05–2–09)
supplementary crystallographic information
Comment
The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions and their biological activity (Salem, 1998; Chang et al., 2007).As an extension of work on the structural characterization of aroylhydrazone derivatives,the title compound, (I),was synthesized and its crystal structure is reported here.
The title molecule displays a trans conformation with respect to the C7=N2 double bond (Fig. 1). The three benzene rings, C1–C6 (A), C9–C14 (B) and C16–C21 (C) make dihedral angles of 10.69 (15)(A/B) °, 79.64 (13) (B/C) °, 73.13 (12)(A/C) °. The molecular conformation is stabilized by intramolecular O—H···N hydrogen bond.(Table 1.) .
Experimental
4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (50 ml), and (3,5-dichloro-2-hydroxyphenyl)(phenyl)methanone (0.01 mol, 2.67 g) was added. The reaction mixture was refluxed for 6 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 78%). The compound (1.0 mmol,0.41 g) was dissolved in dimethylformamide (30 ml) and kept at room temperature for 20 d to obtain colourless single crystals suitable for X-ray diffraction.
Refinement
All H atoms were positioned geometrically and treated as riding on their parent atoms,C—H(methyl) = 0.96 Å,C—H(aromatic) = 0.93 Å, O—H = 0.82 Å, and N—H =0.86 Å and with Uiso(H) =1.5U~eq~(C~methyl~,O) and 1.2Ueq(Caromatic,N).
Figures
Fig. 1.
The molecular structure of compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Crystal data
| C21H15Cl2N2O3 | Z = 2 |
| Mr = 414.25 | F000 = 426 |
| Triclinic, P1 | Dx = 1.400 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 8.9814 (9) Å | Cell parameters from 1372 reflections |
| b = 10.8867 (11) Å | θ = 2.6–23.0º |
| c = 11.5291 (13) Å | µ = 0.36 mm−1 |
| α = 89.623 (2)º | T = 273 (2) K |
| β = 72.700 (1)º | Block, yellow |
| γ = 66.947 (2)º | 0.18 × 0.15 × 0.10 mm |
| V = 982.57 (18) Å3 |
Data collection
| Bruker APEX2 CCD area-detector diffractometer | 3459 independent reflections |
| Radiation source: fine-focus sealed tube | 2262 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.016 |
| T = 298(2) K | θmax = 25.1º |
| φ and ω scans | θmin = 1.9º |
| Absorption correction: multi-scan(SADABS; Sheldrick, 2003) | h = −10→10 |
| Tmin = 0.949, Tmax = 0.965 | k = −12→8 |
| 5254 measured reflections | l = −13→13 |
Refinement
| 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)] = 0.054 | H-atom parameters constrained |
| wR(F2) = 0.207 | w = 1/[σ2(Fo2) + (0.135P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max < 0.001 |
| 3459 reflections | Δρmax = 0.41 e Å−3 |
| 255 parameters | Δρmin = −0.29 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
Special details
| 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)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.51883 (14) | 1.15784 (10) | 0.47405 (9) | 0.0944 (4) | |
| Cl2 | 0.19492 (12) | 1.40951 (10) | 0.93386 (11) | 0.1083 (5) | |
| O1 | 0.4694 (3) | 1.2048 (2) | 0.99251 (19) | 0.0763 (7) | |
| H1 | 0.5549 | 1.1501 | 1.0051 | 0.115* | |
| O2 | 0.7413 (3) | 1.0462 (2) | 1.16739 (19) | 0.0795 (7) | |
| O3 | 1.3151 (3) | 0.5644 (3) | 1.3043 (2) | 0.0845 (7) | |
| N1 | 0.8610 (3) | 0.9057 (3) | 0.9878 (2) | 0.0634 (7) | |
| N2 | 0.7483 (3) | 0.9984 (2) | 0.9403 (2) | 0.0602 (7) | |
| C1 | 0.4846 (4) | 1.1863 (3) | 0.8740 (3) | 0.0598 (8) | |
| C2 | 0.3621 (4) | 1.2797 (3) | 0.8308 (3) | 0.0705 (9) | |
| C3 | 0.3711 (4) | 1.2716 (3) | 0.7099 (4) | 0.0758 (10) | |
| H3 | 0.2875 | 1.3359 | 0.6838 | 0.091* | |
| C4 | 0.5050 (4) | 1.1674 (3) | 0.6276 (3) | 0.0651 (8) | |
| C5 | 0.6262 (4) | 1.0708 (3) | 0.6671 (3) | 0.0592 (8) | |
| H5 | 0.7149 | 0.9998 | 0.6113 | 0.071* | |
| C6 | 0.6180 (3) | 1.0778 (3) | 0.7901 (2) | 0.0533 (7) | |
| C7 | 0.7493 (4) | 0.9727 (3) | 0.8309 (2) | 0.0530 (7) | |
| C8 | 0.8492 (4) | 0.9403 (3) | 1.1074 (3) | 0.0621 (8) | |
| C9 | 0.9766 (4) | 0.8393 (3) | 1.1529 (3) | 0.0590 (8) | |
| C10 | 1.1299 (4) | 0.7433 (4) | 1.0769 (3) | 0.0724 (9) | |
| H10 | 1.1552 | 0.7415 | 0.9925 | 0.087* | |
| C11 | 1.2451 (4) | 0.6506 (4) | 1.1240 (3) | 0.0740 (9) | |
| H11 | 1.3464 | 0.5863 | 1.0713 | 0.089* | |
| C12 | 1.2110 (4) | 0.6527 (3) | 1.2492 (3) | 0.0659 (8) | |
| C13 | 1.0590 (5) | 0.7504 (4) | 1.3255 (3) | 0.0768 (10) | |
| H13 | 1.0346 | 0.7532 | 1.4099 | 0.092* | |
| C14 | 0.9449 (4) | 0.8425 (3) | 1.2786 (3) | 0.0682 (9) | |
| H14 | 0.8449 | 0.9080 | 1.3314 | 0.082* | |
| C15 | 1.4627 (5) | 0.4539 (4) | 1.2293 (4) | 0.0973 (12) | |
| H15A | 1.4296 | 0.4067 | 1.1785 | 0.146* | |
| H15B | 1.5162 | 0.3938 | 1.2804 | 0.146* | |
| H15C | 1.5416 | 0.4867 | 1.1787 | 0.146* | |
| C16 | 0.8695 (4) | 0.8437 (3) | 0.7508 (2) | 0.0533 (7) | |
| C17 | 0.8065 (5) | 0.7546 (4) | 0.7229 (3) | 0.0823 (11) | |
| H17 | 0.6896 | 0.7767 | 0.7513 | 0.099* | |
| C18 | 0.9169 (7) | 0.6327 (4) | 0.6528 (3) | 0.0980 (14) | |
| H18 | 0.8745 | 0.5722 | 0.6352 | 0.118* | |
| C19 | 1.0902 (6) | 0.6004 (4) | 0.6088 (3) | 0.0872 (12) | |
| H19 | 1.1650 | 0.5178 | 0.5623 | 0.105* | |
| C20 | 1.1502 (5) | 0.6900 (4) | 0.6338 (3) | 0.0888 (12) | |
| H20 | 1.2664 | 0.6698 | 0.6020 | 0.107* | |
| C21 | 1.0411 (4) | 0.8108 (4) | 0.7059 (3) | 0.0732 (9) | |
| H21 | 1.0846 | 0.8704 | 0.7240 | 0.088* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.1206 (9) | 0.0939 (7) | 0.0808 (7) | −0.0388 (6) | −0.0560 (6) | 0.0253 (5) |
| Cl2 | 0.0701 (7) | 0.0784 (7) | 0.1367 (10) | −0.0121 (5) | −0.0020 (6) | −0.0271 (6) |
| O1 | 0.0759 (15) | 0.0805 (16) | 0.0590 (14) | −0.0308 (12) | −0.0038 (10) | −0.0138 (11) |
| O2 | 0.0978 (18) | 0.0806 (16) | 0.0510 (13) | −0.0251 (14) | −0.0263 (12) | −0.0083 (12) |
| O3 | 0.0870 (17) | 0.0971 (18) | 0.0738 (15) | −0.0362 (15) | −0.0339 (13) | 0.0216 (14) |
| N1 | 0.0846 (18) | 0.0668 (16) | 0.0454 (13) | −0.0317 (14) | −0.0290 (12) | 0.0054 (11) |
| N2 | 0.0777 (17) | 0.0639 (16) | 0.0463 (13) | −0.0351 (14) | −0.0215 (12) | 0.0012 (11) |
| C1 | 0.0614 (18) | 0.0613 (18) | 0.0589 (18) | −0.0339 (16) | −0.0098 (14) | −0.0040 (15) |
| C2 | 0.0571 (19) | 0.0590 (19) | 0.087 (2) | −0.0243 (16) | −0.0104 (17) | −0.0079 (17) |
| C3 | 0.071 (2) | 0.066 (2) | 0.101 (3) | −0.0302 (18) | −0.039 (2) | 0.015 (2) |
| C4 | 0.070 (2) | 0.0637 (19) | 0.069 (2) | −0.0283 (17) | −0.0309 (16) | 0.0112 (16) |
| C5 | 0.0643 (18) | 0.0567 (18) | 0.0554 (17) | −0.0244 (15) | −0.0179 (14) | −0.0001 (14) |
| C6 | 0.0551 (16) | 0.0565 (17) | 0.0498 (16) | −0.0276 (14) | −0.0122 (13) | −0.0019 (13) |
| C7 | 0.0636 (18) | 0.0545 (17) | 0.0455 (15) | −0.0302 (14) | −0.0154 (13) | 0.0020 (12) |
| C8 | 0.080 (2) | 0.073 (2) | 0.0429 (16) | −0.0417 (19) | −0.0183 (15) | 0.0023 (15) |
| C9 | 0.074 (2) | 0.0704 (19) | 0.0458 (16) | −0.0408 (17) | −0.0215 (14) | 0.0058 (14) |
| C10 | 0.081 (2) | 0.088 (2) | 0.0477 (17) | −0.037 (2) | −0.0169 (16) | 0.0012 (17) |
| C11 | 0.071 (2) | 0.086 (2) | 0.0569 (19) | −0.0280 (19) | −0.0154 (16) | 0.0015 (17) |
| C12 | 0.074 (2) | 0.080 (2) | 0.0621 (19) | −0.0468 (18) | −0.0279 (16) | 0.0175 (17) |
| C13 | 0.095 (3) | 0.091 (3) | 0.0427 (16) | −0.037 (2) | −0.0204 (17) | 0.0117 (17) |
| C14 | 0.081 (2) | 0.075 (2) | 0.0438 (16) | −0.0306 (18) | −0.0156 (15) | 0.0047 (15) |
| C15 | 0.078 (3) | 0.105 (3) | 0.107 (3) | −0.032 (2) | −0.035 (2) | 0.025 (3) |
| C16 | 0.0698 (19) | 0.0551 (17) | 0.0394 (14) | −0.0264 (15) | −0.0221 (13) | 0.0045 (12) |
| C17 | 0.103 (3) | 0.083 (2) | 0.062 (2) | −0.057 (2) | −0.0013 (18) | −0.0132 (18) |
| C18 | 0.154 (4) | 0.075 (3) | 0.064 (2) | −0.067 (3) | −0.005 (2) | −0.0078 (19) |
| C19 | 0.127 (4) | 0.060 (2) | 0.053 (2) | −0.013 (2) | −0.033 (2) | 0.0035 (16) |
| C20 | 0.074 (2) | 0.094 (3) | 0.077 (2) | −0.006 (2) | −0.0326 (19) | −0.018 (2) |
| C21 | 0.068 (2) | 0.079 (2) | 0.072 (2) | −0.0252 (18) | −0.0255 (16) | −0.0107 (17) |
Geometric parameters (Å, °)
| Cl1—C4 | 1.738 (3) | C10—C11 | 1.376 (5) |
| Cl2—C2 | 1.722 (3) | C10—H10 | 0.9300 |
| O1—C1 | 1.340 (4) | C11—C12 | 1.382 (5) |
| O1—H1 | 0.8200 | C11—H11 | 0.9300 |
| O2—C8 | 1.217 (4) | C12—C13 | 1.389 (5) |
| O3—C12 | 1.358 (4) | C13—C14 | 1.365 (5) |
| O3—C15 | 1.427 (4) | C13—H13 | 0.9300 |
| N1—N2 | 1.366 (4) | C14—H14 | 0.9300 |
| N1—C8 | 1.394 (4) | C15—H15A | 0.9600 |
| N2—C7 | 1.291 (3) | C15—H15B | 0.9600 |
| C1—C2 | 1.391 (5) | C15—H15C | 0.9600 |
| C1—C6 | 1.408 (4) | C16—C21 | 1.367 (4) |
| C2—C3 | 1.374 (5) | C16—C17 | 1.381 (4) |
| C3—C4 | 1.378 (4) | C17—C18 | 1.380 (5) |
| C3—H3 | 0.9300 | C17—H17 | 0.9300 |
| C4—C5 | 1.375 (4) | C18—C19 | 1.381 (5) |
| C5—C6 | 1.399 (4) | C18—H18 | 0.9300 |
| C5—H5 | 0.9300 | C19—C20 | 1.354 (5) |
| C6—C7 | 1.479 (4) | C19—H19 | 0.9300 |
| C7—C16 | 1.492 (4) | C20—C21 | 1.379 (5) |
| C8—C9 | 1.469 (5) | C20—H20 | 0.9300 |
| C9—C10 | 1.387 (4) | C21—H21 | 0.9300 |
| C9—C14 | 1.390 (4) | ||
| C1—O1—H1 | 109.5 | C10—C11—H11 | 119.9 |
| C12—O3—C15 | 118.3 (3) | C12—C11—H11 | 119.9 |
| N2—N1—C8 | 116.5 (3) | O3—C12—C11 | 124.7 (3) |
| C7—N2—N1 | 120.2 (2) | O3—C12—C13 | 116.8 (3) |
| O1—C1—C2 | 118.3 (3) | C11—C12—C13 | 118.5 (3) |
| O1—C1—C6 | 123.8 (3) | C14—C13—C12 | 121.1 (3) |
| C2—C1—C6 | 117.8 (3) | C14—C13—H13 | 119.4 |
| C3—C2—C1 | 122.3 (3) | C12—C13—H13 | 119.4 |
| C3—C2—Cl2 | 119.6 (3) | C13—C14—C9 | 120.7 (3) |
| C1—C2—Cl2 | 118.1 (3) | C13—C14—H14 | 119.6 |
| C2—C3—C4 | 119.5 (3) | C9—C14—H14 | 119.6 |
| C2—C3—H3 | 120.3 | O3—C15—H15A | 109.5 |
| C4—C3—H3 | 120.3 | O3—C15—H15B | 109.5 |
| C5—C4—C3 | 120.1 (3) | H15A—C15—H15B | 109.5 |
| C5—C4—Cl1 | 120.2 (3) | O3—C15—H15C | 109.5 |
| C3—C4—Cl1 | 119.8 (3) | H15A—C15—H15C | 109.5 |
| C4—C5—C6 | 120.9 (3) | H15B—C15—H15C | 109.5 |
| C4—C5—H5 | 119.5 | C21—C16—C17 | 119.2 (3) |
| C6—C5—H5 | 119.5 | C21—C16—C7 | 121.4 (3) |
| C5—C6—C1 | 119.3 (3) | C17—C16—C7 | 119.4 (3) |
| C5—C6—C7 | 120.1 (3) | C18—C17—C16 | 120.0 (4) |
| C1—C6—C7 | 120.6 (3) | C18—C17—H17 | 120.0 |
| N2—C7—C6 | 115.7 (2) | C16—C17—H17 | 120.0 |
| N2—C7—C16 | 123.0 (3) | C17—C18—C19 | 120.2 (4) |
| C6—C7—C16 | 121.2 (2) | C17—C18—H18 | 119.9 |
| O2—C8—N1 | 121.7 (3) | C19—C18—H18 | 119.9 |
| O2—C8—C9 | 123.9 (3) | C20—C19—C18 | 119.4 (3) |
| N1—C8—C9 | 114.4 (3) | C20—C19—H19 | 120.3 |
| C10—C9—C14 | 118.0 (3) | C18—C19—H19 | 120.3 |
| C10—C9—C8 | 123.5 (3) | C19—C20—C21 | 120.8 (4) |
| C14—C9—C8 | 118.5 (3) | C19—C20—H20 | 119.6 |
| C11—C10—C9 | 121.3 (3) | C21—C20—H20 | 119.6 |
| C11—C10—H10 | 119.3 | C16—C21—C20 | 120.4 (3) |
| C9—C10—H10 | 119.3 | C16—C21—H21 | 119.8 |
| C10—C11—C12 | 120.3 (3) | C20—C21—H21 | 119.8 |
| C8—N1—N2—C7 | −178.8 (2) | O2—C8—C9—C14 | 19.9 (5) |
| O1—C1—C2—C3 | 177.5 (3) | N1—C8—C9—C14 | −160.2 (3) |
| C6—C1—C2—C3 | −2.3 (5) | C14—C9—C10—C11 | 2.2 (5) |
| O1—C1—C2—Cl2 | −2.2 (4) | C8—C9—C10—C11 | −179.9 (3) |
| C6—C1—C2—Cl2 | 177.9 (2) | C9—C10—C11—C12 | −0.9 (5) |
| C1—C2—C3—C4 | 0.3 (5) | C15—O3—C12—C11 | −6.0 (5) |
| Cl2—C2—C3—C4 | −179.9 (2) | C15—O3—C12—C13 | 173.2 (3) |
| C2—C3—C4—C5 | 1.5 (5) | C10—C11—C12—O3 | 178.8 (3) |
| C2—C3—C4—Cl1 | −179.1 (2) | C10—C11—C12—C13 | −0.3 (5) |
| C3—C4—C5—C6 | −1.3 (5) | O3—C12—C13—C14 | −179.0 (3) |
| Cl1—C4—C5—C6 | 179.3 (2) | C11—C12—C13—C14 | 0.2 (5) |
| C4—C5—C6—C1 | −0.7 (4) | C12—C13—C14—C9 | 1.1 (6) |
| C4—C5—C6—C7 | 179.8 (3) | C10—C9—C14—C13 | −2.3 (5) |
| O1—C1—C6—C5 | −177.4 (3) | C8—C9—C14—C13 | 179.7 (3) |
| C2—C1—C6—C5 | 2.5 (4) | N2—C7—C16—C21 | −67.8 (4) |
| O1—C1—C6—C7 | 2.1 (4) | C6—C7—C16—C21 | 114.8 (3) |
| C2—C1—C6—C7 | −178.1 (3) | N2—C7—C16—C17 | 111.3 (3) |
| N1—N2—C7—C6 | 177.9 (2) | C6—C7—C16—C17 | −66.2 (4) |
| N1—N2—C7—C16 | 0.3 (4) | C21—C16—C17—C18 | 1.5 (5) |
| C5—C6—C7—N2 | 169.1 (2) | C7—C16—C17—C18 | −177.6 (3) |
| C1—C6—C7—N2 | −10.4 (4) | C16—C17—C18—C19 | −1.1 (6) |
| C5—C6—C7—C16 | −13.3 (4) | C17—C18—C19—C20 | −0.8 (6) |
| C1—C6—C7—C16 | 167.2 (2) | C18—C19—C20—C21 | 2.1 (6) |
| N2—N1—C8—O2 | 1.7 (4) | C17—C16—C21—C20 | −0.2 (5) |
| N2—N1—C8—C9 | −178.2 (2) | C7—C16—C21—C20 | 178.9 (3) |
| O2—C8—C9—C10 | −157.9 (3) | C19—C20—C21—C16 | −1.7 (5) |
| N1—C8—C9—C10 | 22.0 (4) |
Hydrogen-bond geometry (Å, °)
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N2 | 0.82 | 1.82 | 2.528 (3) | 145 |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GD2026).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064069/gd2026sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064069/gd2026Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report