Acta Cryst. (2011). E67, o410 [ doi:10.1107/S1600536811001656 ]
The title compound, C14H10Cl2N2O, was prepared from the reaction of 2-chlorobenzaldehyde with 3-chlorobenzohydrazide in methanol. The molecule adopts an E configuration about the methylidene unit and the two aromatic rings form a dihedral angle of 13.8 (2)°. In the crystal, molecules are linked via intermolecular N-H
O and C-HO hydrogen bonds, forming chains along the c axis.
3-Chlorobenzohydrazide (1 mmol, 0.170 g) was dissolved in methanol (50 ml), then 2-chlorobenzaldehyde (1 mmol, 0.140 g) was added into the solution. The reaction mixture was heated under reflux for 1 h and cooled to room temperature. Colourless needle-shaped crystals were formed by slow evaporation of the solvent for a week.
The amino H atom was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. Other H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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]](./qm2001fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids. |
![[Figure 2]](./qm2001fig2thm.gif)
| Fig. 2. The molecular packing of the title compound. Hydrogen bonding is shown in dashed lines. |
| C14H10Cl2N2O | F(000) = 600 |
| Mr = 293.14 | Dx = 1.426 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 13.106 (3) Å | Cell parameters from 1672 reflections |
| b = 12.588 (3) Å | θ = 2.2–25.0° |
| c = 8.347 (2) Å | µ = 0.47 mm−1 |
| β = 97.578 (2)° | T = 298 K |
| V = 1365.0 (6) Å3 | Cut from needle, colourless |
| Z = 4 | 0.32 × 0.30 × 0.30 mm |
| Bruker SMART CCD area-detector diffractometer | 2954 independent reflections |
| Radiation source: fine-focus sealed tube | 1936 reflections with I > 2σ(I) |
| graphite | Rint = 0.032 |
| ω scans | θmax = 27.0°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −16→8 |
| Tmin = 0.865, Tmax = 0.873 | k = −15→15 |
| 6893 measured reflections | l = −10→10 |
| 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) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3 |
| 2954 reflections | (Δ/σ)max < 0.001 |
| 175 parameters | Δρmax = 0.26 e Å−3 |
| 1 restraint | Δρmin = −0.48 e Å−3 |
| C14H10Cl2N2O | V = 1365.0 (6) Å3 |
| Mr = 293.14 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 13.106 (3) Å | µ = 0.47 mm−1 |
| b = 12.588 (3) Å | T = 298 K |
| c = 8.347 (2) Å | 0.32 × 0.30 × 0.30 mm |
| β = 97.578 (2)° |
| Bruker SMART CCD area-detector diffractometer | 2954 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1936 reflections with I > 2σ(I) |
| Tmin = 0.865, Tmax = 0.873 | Rint = 0.032 |
| 6893 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.130 | Δρmax = 0.26 e Å−3 |
| S = 1.01 | Δρmin = −0.48 e Å−3 |
| 2954 reflections | Absolute structure: ? |
| 175 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
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 | 0.21684 (6) | 1.16019 (5) | 0.46800 (10) | 0.0837 (3) | |
| Cl2 | 0.53314 (6) | 0.63298 (7) | 0.15637 (9) | 0.0856 (3) | |
| N1 | 0.19380 (12) | 0.83421 (13) | 0.60855 (18) | 0.0400 (4) | |
| N2 | 0.24735 (13) | 0.76623 (13) | 0.51905 (19) | 0.0427 (4) | |
| O1 | 0.26043 (12) | 0.63872 (10) | 0.71199 (17) | 0.0540 (4) | |
| C1 | 0.12399 (14) | 1.00751 (15) | 0.6282 (2) | 0.0385 (5) | |
| C2 | 0.12993 (16) | 1.11524 (18) | 0.5925 (3) | 0.0490 (5) | |
| C3 | 0.06753 (19) | 1.18886 (19) | 0.6553 (3) | 0.0611 (6) | |
| H3 | 0.0727 | 1.2605 | 0.6301 | 0.073* | |
| C4 | −0.0017 (2) | 1.1565 (2) | 0.7544 (3) | 0.0632 (7) | |
| H4 | −0.0443 | 1.2059 | 0.7952 | 0.076* | |
| C5 | −0.00819 (18) | 1.0505 (2) | 0.7936 (3) | 0.0587 (6) | |
| H5 | −0.0545 | 1.0284 | 0.8622 | 0.070* | |
| C6 | 0.05422 (16) | 0.97729 (17) | 0.7309 (2) | 0.0481 (5) | |
| H6 | 0.0494 | 0.9060 | 0.7581 | 0.058* | |
| C7 | 0.18546 (15) | 0.92841 (16) | 0.5543 (2) | 0.0421 (5) | |
| H7 | 0.2187 | 0.9475 | 0.4668 | 0.050* | |
| C8 | 0.27659 (15) | 0.66994 (15) | 0.5784 (2) | 0.0395 (5) | |
| C9 | 0.33107 (14) | 0.60210 (16) | 0.4702 (2) | 0.0385 (5) | |
| C10 | 0.39762 (14) | 0.64550 (17) | 0.3718 (2) | 0.0434 (5) | |
| H10 | 0.4085 | 0.7185 | 0.3701 | 0.052* | |
| C11 | 0.44732 (15) | 0.57875 (19) | 0.2767 (2) | 0.0491 (5) | |
| C12 | 0.43214 (18) | 0.4709 (2) | 0.2764 (3) | 0.0604 (6) | |
| H12 | 0.4660 | 0.4271 | 0.2108 | 0.073* | |
| C13 | 0.36611 (18) | 0.4287 (2) | 0.3747 (3) | 0.0597 (6) | |
| H13 | 0.3549 | 0.3558 | 0.3750 | 0.072* | |
| C14 | 0.31610 (16) | 0.49373 (16) | 0.4730 (2) | 0.0480 (5) | |
| H14 | 0.2726 | 0.4645 | 0.5406 | 0.058* | |
| H2 | 0.2558 (19) | 0.784 (2) | 0.4177 (15) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0797 (5) | 0.0687 (5) | 0.1097 (6) | 0.0039 (3) | 0.0387 (4) | 0.0327 (4) |
| Cl2 | 0.0801 (5) | 0.1113 (6) | 0.0754 (5) | 0.0101 (4) | 0.0480 (4) | 0.0065 (4) |
| N1 | 0.0445 (9) | 0.0439 (10) | 0.0329 (9) | 0.0052 (7) | 0.0100 (7) | −0.0031 (7) |
| N2 | 0.0552 (10) | 0.0449 (10) | 0.0309 (9) | 0.0109 (8) | 0.0159 (8) | 0.0019 (7) |
| O1 | 0.0810 (11) | 0.0488 (9) | 0.0364 (8) | 0.0073 (7) | 0.0237 (7) | 0.0049 (6) |
| C1 | 0.0390 (10) | 0.0428 (12) | 0.0332 (10) | 0.0044 (8) | 0.0028 (8) | −0.0010 (8) |
| C2 | 0.0436 (11) | 0.0519 (14) | 0.0509 (13) | 0.0030 (10) | 0.0043 (9) | 0.0033 (10) |
| C3 | 0.0637 (14) | 0.0438 (13) | 0.0743 (17) | 0.0098 (11) | 0.0037 (13) | −0.0032 (12) |
| C4 | 0.0640 (15) | 0.0614 (16) | 0.0644 (16) | 0.0179 (12) | 0.0092 (13) | −0.0153 (12) |
| C5 | 0.0548 (13) | 0.0700 (16) | 0.0540 (14) | 0.0091 (12) | 0.0177 (11) | −0.0036 (12) |
| C6 | 0.0507 (12) | 0.0467 (12) | 0.0482 (13) | 0.0017 (10) | 0.0116 (10) | −0.0008 (10) |
| C7 | 0.0435 (11) | 0.0482 (12) | 0.0357 (11) | 0.0037 (9) | 0.0098 (8) | 0.0013 (9) |
| C8 | 0.0427 (11) | 0.0438 (12) | 0.0331 (11) | 0.0010 (9) | 0.0092 (8) | 0.0002 (9) |
| C9 | 0.0376 (10) | 0.0452 (12) | 0.0323 (10) | 0.0052 (8) | 0.0033 (8) | −0.0015 (8) |
| C10 | 0.0449 (11) | 0.0507 (13) | 0.0351 (11) | 0.0046 (9) | 0.0072 (9) | −0.0016 (9) |
| C11 | 0.0445 (11) | 0.0647 (15) | 0.0400 (12) | 0.0093 (10) | 0.0122 (9) | −0.0011 (10) |
| C12 | 0.0610 (14) | 0.0699 (17) | 0.0511 (14) | 0.0208 (12) | 0.0102 (12) | −0.0151 (12) |
| C13 | 0.0675 (15) | 0.0473 (14) | 0.0640 (16) | 0.0079 (11) | 0.0077 (12) | −0.0082 (11) |
| C14 | 0.0502 (12) | 0.0478 (13) | 0.0468 (13) | 0.0037 (10) | 0.0089 (10) | 0.0005 (10) |
| Cl1—C2 | 1.735 (2) | C5—C6 | 1.380 (3) |
| Cl2—C11 | 1.743 (2) | C5—H5 | 0.9300 |
| N1—C7 | 1.269 (2) | C6—H6 | 0.9300 |
| N1—N2 | 1.386 (2) | C7—H7 | 0.9300 |
| N2—C8 | 1.346 (2) | C8—C9 | 1.491 (3) |
| N2—H2 | 0.895 (10) | C9—C14 | 1.379 (3) |
| O1—C8 | 1.227 (2) | C9—C10 | 1.387 (3) |
| C1—C6 | 1.387 (3) | C10—C11 | 1.377 (3) |
| C1—C2 | 1.393 (3) | C10—H10 | 0.9300 |
| C1—C7 | 1.467 (3) | C11—C12 | 1.372 (3) |
| C2—C3 | 1.384 (3) | C12—C13 | 1.375 (3) |
| C3—C4 | 1.368 (4) | C12—H12 | 0.9300 |
| C3—H3 | 0.9300 | C13—C14 | 1.384 (3) |
| C4—C5 | 1.379 (3) | C13—H13 | 0.9300 |
| C4—H4 | 0.9300 | C14—H14 | 0.9300 |
| C7—N1—N2 | 114.25 (16) | N1—C7—H7 | 119.6 |
| C8—N2—N1 | 119.83 (15) | C1—C7—H7 | 119.6 |
| C8—N2—H2 | 120.5 (17) | O1—C8—N2 | 123.24 (18) |
| N1—N2—H2 | 119.3 (17) | O1—C8—C9 | 121.38 (18) |
| C6—C1—C2 | 117.34 (18) | N2—C8—C9 | 115.39 (16) |
| C6—C1—C7 | 121.13 (18) | C14—C9—C10 | 120.11 (19) |
| C2—C1—C7 | 121.46 (19) | C14—C9—C8 | 118.42 (18) |
| C3—C2—C1 | 121.2 (2) | C10—C9—C8 | 121.45 (18) |
| C3—C2—Cl1 | 118.42 (19) | C11—C10—C9 | 118.9 (2) |
| C1—C2—Cl1 | 120.35 (16) | C11—C10—H10 | 120.6 |
| C4—C3—C2 | 120.1 (2) | C9—C10—H10 | 120.6 |
| C4—C3—H3 | 119.9 | C12—C11—C10 | 121.7 (2) |
| C2—C3—H3 | 119.9 | C12—C11—Cl2 | 119.40 (17) |
| C3—C4—C5 | 119.9 (2) | C10—C11—Cl2 | 118.91 (18) |
| C3—C4—H4 | 120.1 | C11—C12—C13 | 118.9 (2) |
| C5—C4—H4 | 120.1 | C11—C12—H12 | 120.5 |
| C4—C5—C6 | 119.9 (2) | C13—C12—H12 | 120.5 |
| C4—C5—H5 | 120.1 | C12—C13—C14 | 120.7 (2) |
| C6—C5—H5 | 120.1 | C12—C13—H13 | 119.7 |
| C5—C6—C1 | 121.6 (2) | C14—C13—H13 | 119.7 |
| C5—C6—H6 | 119.2 | C9—C14—C13 | 119.7 (2) |
| C1—C6—H6 | 119.2 | C9—C14—H14 | 120.1 |
| N1—C7—C1 | 120.73 (18) | C13—C14—H14 | 120.1 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1i | 0.90 (1) | 1.98 (1) | 2.854 (2) | 164 (2) |
| C7—H7···O1i | 0.93 | 2.51 | 3.254 (2) | 137 (2) |
| Symmetry codes: (i) x, −y+3/2, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1i | 0.90 (1) | 1.98 (1) | 2.854 (2) | 164 (2) |
| C7—H7···O1i | 0.93 | 2.51 | 3.254 (2) | 137 (2) |
| Symmetry codes: (i) x, −y+3/2, z−1/2. |
The authors acknowledge financial support from the Chongqing Three Gorges University.
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In recent years, much effort has been devoted for developing the hydrazones, due to their biological properties, coordinative capability, and applications in analytical chemistry (El-Asmy et al., 2010; El-Sherif, 2009; Singh et al., 2009; El-Tabl et al., 2007). Recently, a number of hydrazones have been prepared and investigated for their structures (Qiao et al., 2010; Hussain et al., 2010; Han & Zhao, 2010; Ahmad et al., 2010; Lei, 2011). As a continuation of hydrazones, the author reports herein the title new compound.
The molecule of the title compound, Fig. 1, adopts an E configuration about the methylidene unit. The two aromatic rings form a dihedral angle of 13.8 (2)°. In the crystal, the molecules are linked via intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), to form chains at the c-axis direction (Fig. 2).