Acta Cryst. (2008). E64, o2319 [ doi:10.1107/S1600536808036386 ]
In the title molecule, C15H15ClN2, the dihedral angle between the aromatic is 64.1 (2)°.
A mixture of 4-(dimethylamino)benzaldehyde (0.01 mol) and 2-chlorobenzenamine (0.01 mol) in ethanol (10 ml) was refluxed for 2 h. After cooling, filtration and drying, the title compound was obtained. 10 mg of (I) were dissolved in 15 ml of ethanol, and the solution was kept at room temperature for 5 d. Natural evaporation gave light yellow single crystals of the title compound, suitable for X-ray analysis.
H atoms were initially located from difference maps and then refined in a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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).
| C15H15ClN2 | F(000) = 544 |
| Mr = 258.74 | Dx = 1.297 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 1182 reflections |
| a = 7.7301 (8) Å | θ = 2.9–20.1° |
| b = 12.2016 (18) Å | µ = 0.27 mm−1 |
| c = 14.047 (2) Å | T = 298 K |
| V = 1325.0 (3) Å3 | Block, light yellow |
| Z = 4 | 0.45 × 0.38 × 0.30 mm |
| Bruker SMART CCD diffractometer | 2318 independent reflections |
| Radiation source: fine-focus sealed tube | 1391 reflections with I > 2σ(I) |
| graphite | Rint = 0.054 |
| φ and ω scans | θmax = 25.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −9→9 |
| Tmin = 0.888, Tmax = 0.923 | k = −14→13 |
| 5507 measured reflections | l = −9→16 |
| 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-atom parameters constrained |
| wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0377P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 2318 reflections | Δρmax = 0.18 e Å−3 |
| 165 parameters | Δρmin = −0.18 e Å−3 |
| 0 restraints | Absolute structure: Flack (1983), 1358 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: −0.07 (10) |
| C15H15ClN2 | V = 1325.0 (3) Å3 |
| Mr = 258.74 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 7.7301 (8) Å | µ = 0.27 mm−1 |
| b = 12.2016 (18) Å | T = 298 K |
| c = 14.047 (2) Å | 0.45 × 0.38 × 0.30 mm |
| Bruker SMART CCD diffractometer | 2318 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1391 reflections with I > 2σ(I) |
| Tmin = 0.888, Tmax = 0.923 | Rint = 0.054 |
| 5507 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.105 | Δρmax = 0.18 e Å−3 |
| S = 1.02 | Δρmin = −0.18 e Å−3 |
| 2318 reflections | Absolute structure: Flack (1983), 1358 Friedel pairs |
| 165 parameters | Flack parameter: −0.07 (10) |
| 0 restraints |
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 | 1.22788 (14) | 1.11816 (8) | −0.13149 (7) | 0.0753 (4) | |
| N1 | 0.9918 (4) | 0.9322 (2) | −0.09661 (18) | 0.0513 (8) | |
| N2 | 0.8770 (4) | 0.7449 (2) | 0.32629 (18) | 0.0555 (8) | |
| C1 | 1.0238 (4) | 0.8391 (3) | −0.0595 (2) | 0.0477 (9) | |
| H1 | 1.0788 | 0.7861 | −0.0962 | 0.057* | |
| C2 | 0.9776 (4) | 0.8127 (2) | 0.0381 (2) | 0.0436 (9) | |
| C3 | 0.8837 (4) | 0.8839 (3) | 0.0949 (2) | 0.0460 (9) | |
| H3 | 0.8439 | 0.9491 | 0.0686 | 0.055* | |
| C4 | 0.8472 (5) | 0.8618 (3) | 0.1884 (2) | 0.0478 (9) | |
| H4 | 0.7815 | 0.9112 | 0.2235 | 0.057* | |
| C5 | 0.9077 (4) | 0.7656 (3) | 0.2319 (2) | 0.0441 (9) | |
| C6 | 0.9993 (5) | 0.6920 (3) | 0.1744 (2) | 0.0498 (9) | |
| H6 | 1.0379 | 0.6261 | 0.2002 | 0.060* | |
| C7 | 1.0331 (5) | 0.7156 (3) | 0.0807 (2) | 0.0510 (10) | |
| H7 | 1.0949 | 0.6652 | 0.0445 | 0.061* | |
| C8 | 0.7854 (5) | 0.8221 (3) | 0.3849 (2) | 0.0719 (12) | |
| H8A | 0.8528 | 0.8878 | 0.3913 | 0.108* | |
| H8B | 0.7660 | 0.7908 | 0.4467 | 0.108* | |
| H8C | 0.6763 | 0.8394 | 0.3559 | 0.108* | |
| C9 | 0.9648 (5) | 0.6548 (3) | 0.3736 (2) | 0.0671 (11) | |
| H9A | 0.9342 | 0.5870 | 0.3432 | 0.101* | |
| H9B | 0.9305 | 0.6524 | 0.4393 | 0.101* | |
| H9C | 1.0876 | 0.6654 | 0.3696 | 0.101* | |
| C10 | 1.0315 (5) | 0.9502 (3) | −0.1928 (2) | 0.0452 (9) | |
| C11 | 1.1315 (4) | 1.0405 (3) | −0.2197 (2) | 0.0481 (9) | |
| C12 | 1.1594 (5) | 1.0664 (3) | −0.3137 (2) | 0.0595 (10) | |
| H12 | 1.2266 | 1.1269 | −0.3298 | 0.071* | |
| C13 | 1.0873 (5) | 1.0020 (3) | −0.3841 (3) | 0.0654 (11) | |
| H13 | 1.1042 | 1.0197 | −0.4478 | 0.078* | |
| C14 | 0.9911 (5) | 0.9125 (3) | −0.3600 (3) | 0.0661 (11) | |
| H14 | 0.9451 | 0.8682 | −0.4075 | 0.079* | |
| C15 | 0.9612 (5) | 0.8869 (3) | −0.2650 (2) | 0.0587 (10) | |
| H15 | 0.8932 | 0.8266 | −0.2497 | 0.070* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0818 (8) | 0.0730 (7) | 0.0711 (6) | −0.0204 (6) | −0.0003 (6) | −0.0069 (5) |
| N1 | 0.060 (2) | 0.0516 (17) | 0.0423 (16) | −0.0012 (18) | 0.0060 (16) | 0.0035 (14) |
| N2 | 0.053 (2) | 0.069 (2) | 0.0440 (17) | 0.0048 (18) | 0.0025 (15) | 0.0064 (15) |
| C1 | 0.048 (3) | 0.050 (2) | 0.045 (2) | −0.0014 (19) | −0.0003 (19) | −0.0074 (17) |
| C2 | 0.046 (2) | 0.0450 (19) | 0.0397 (19) | −0.0033 (19) | 0.0012 (18) | −0.0035 (16) |
| C3 | 0.049 (2) | 0.0394 (18) | 0.049 (2) | 0.0003 (19) | −0.0047 (17) | 0.0001 (18) |
| C4 | 0.050 (2) | 0.048 (2) | 0.045 (2) | 0.0075 (17) | 0.0021 (18) | −0.0034 (17) |
| C5 | 0.042 (2) | 0.052 (2) | 0.0386 (19) | −0.0057 (18) | −0.0011 (17) | −0.0029 (18) |
| C6 | 0.057 (3) | 0.0407 (19) | 0.051 (2) | 0.005 (2) | −0.003 (2) | 0.0055 (17) |
| C7 | 0.056 (3) | 0.049 (2) | 0.048 (2) | 0.0044 (19) | 0.0023 (19) | −0.0053 (18) |
| C8 | 0.076 (3) | 0.095 (3) | 0.045 (2) | 0.004 (3) | 0.012 (2) | −0.002 (2) |
| C9 | 0.062 (3) | 0.078 (3) | 0.061 (2) | −0.007 (2) | −0.004 (2) | 0.024 (2) |
| C10 | 0.047 (2) | 0.046 (2) | 0.043 (2) | 0.0044 (19) | 0.0025 (19) | 0.0001 (17) |
| C11 | 0.047 (2) | 0.050 (2) | 0.047 (2) | 0.0046 (19) | 0.0041 (19) | 0.0020 (17) |
| C12 | 0.058 (3) | 0.063 (2) | 0.058 (2) | −0.002 (2) | 0.014 (2) | 0.009 (2) |
| C13 | 0.069 (3) | 0.081 (3) | 0.046 (2) | 0.019 (2) | 0.008 (2) | 0.008 (2) |
| C14 | 0.068 (3) | 0.080 (3) | 0.050 (2) | 0.007 (3) | −0.006 (2) | −0.007 (2) |
| C15 | 0.062 (3) | 0.057 (2) | 0.057 (2) | −0.003 (2) | 0.000 (2) | −0.001 (2) |
| Cl1—C11 | 1.728 (3) | C7—H7 | 0.9300 |
| N1—C1 | 1.274 (3) | C8—H8A | 0.9600 |
| N1—C10 | 1.403 (4) | C8—H8B | 0.9600 |
| N2—C5 | 1.371 (4) | C8—H8C | 0.9600 |
| N2—C8 | 1.438 (4) | C9—H9A | 0.9600 |
| N2—C9 | 1.453 (4) | C9—H9B | 0.9600 |
| C1—C2 | 1.453 (4) | C9—H9C | 0.9600 |
| C1—H1 | 0.9300 | C10—C15 | 1.385 (4) |
| C2—C3 | 1.385 (4) | C10—C11 | 1.398 (4) |
| C2—C7 | 1.395 (4) | C11—C12 | 1.376 (4) |
| C3—C4 | 1.369 (4) | C12—C13 | 1.379 (5) |
| C3—H3 | 0.9300 | C12—H12 | 0.9300 |
| C4—C5 | 1.404 (4) | C13—C14 | 1.364 (5) |
| C4—H4 | 0.9300 | C13—H13 | 0.9300 |
| C5—C6 | 1.400 (4) | C14—C15 | 1.390 (4) |
| C6—C7 | 1.373 (4) | C14—H14 | 0.9300 |
| C6—H6 | 0.9300 | C15—H15 | 0.9300 |
| ?···? | ? | ||
| C1—N1—C10 | 119.4 (3) | N2—C8—H8C | 109.5 |
| C5—N2—C8 | 121.2 (3) | H8A—C8—H8C | 109.5 |
| C5—N2—C9 | 120.1 (3) | H8B—C8—H8C | 109.5 |
| C8—N2—C9 | 117.6 (3) | N2—C9—H9A | 109.5 |
| N1—C1—C2 | 122.5 (3) | N2—C9—H9B | 109.5 |
| N1—C1—H1 | 118.8 | H9A—C9—H9B | 109.5 |
| C2—C1—H1 | 118.8 | N2—C9—H9C | 109.5 |
| C3—C2—C7 | 116.5 (3) | H9A—C9—H9C | 109.5 |
| C3—C2—C1 | 122.2 (3) | H9B—C9—H9C | 109.5 |
| C7—C2—C1 | 121.2 (3) | C15—C10—C11 | 117.3 (3) |
| C4—C3—C2 | 122.5 (3) | C15—C10—N1 | 122.2 (3) |
| C4—C3—H3 | 118.7 | C11—C10—N1 | 120.2 (3) |
| C2—C3—H3 | 118.7 | C12—C11—C10 | 121.8 (3) |
| C3—C4—C5 | 120.9 (3) | C12—C11—Cl1 | 119.7 (3) |
| C3—C4—H4 | 119.6 | C10—C11—Cl1 | 118.5 (3) |
| C5—C4—H4 | 119.6 | C11—C12—C13 | 119.6 (3) |
| N2—C5—C6 | 121.8 (3) | C11—C12—H12 | 120.2 |
| N2—C5—C4 | 121.2 (3) | C13—C12—H12 | 120.2 |
| C6—C5—C4 | 117.0 (3) | C14—C13—C12 | 119.9 (3) |
| C7—C6—C5 | 121.0 (3) | C14—C13—H13 | 120.0 |
| C7—C6—H6 | 119.5 | C12—C13—H13 | 120.0 |
| C5—C6—H6 | 119.5 | C13—C14—C15 | 120.6 (4) |
| C6—C7—C2 | 122.1 (3) | C13—C14—H14 | 119.7 |
| C6—C7—H7 | 119.0 | C15—C14—H14 | 119.7 |
| C2—C7—H7 | 119.0 | C10—C15—C14 | 120.8 (3) |
| N2—C8—H8A | 109.5 | C10—C15—H15 | 119.6 |
| N2—C8—H8B | 109.5 | C14—C15—H15 | 119.6 |
| H8A—C8—H8B | 109.5 | ||
| C10—N1—C1—C2 | −176.5 (3) | C3—C2—C7—C6 | −1.0 (5) |
| N1—C1—C2—C3 | 5.2 (5) | C1—C2—C7—C6 | 176.2 (3) |
| N1—C1—C2—C7 | −171.9 (3) | C1—N1—C10—C15 | 58.8 (5) |
| C7—C2—C3—C4 | 0.5 (5) | C1—N1—C10—C11 | −127.5 (4) |
| C1—C2—C3—C4 | −176.7 (3) | C15—C10—C11—C12 | 0.1 (5) |
| C2—C3—C4—C5 | 1.4 (5) | N1—C10—C11—C12 | −173.9 (3) |
| C8—N2—C5—C6 | 178.9 (3) | C15—C10—C11—Cl1 | −177.6 (2) |
| C9—N2—C5—C6 | 10.8 (5) | N1—C10—C11—Cl1 | 8.4 (4) |
| C8—N2—C5—C4 | −1.6 (5) | C10—C11—C12—C13 | 0.1 (5) |
| C9—N2—C5—C4 | −169.6 (3) | Cl1—C11—C12—C13 | 177.7 (3) |
| C3—C4—C5—N2 | 177.6 (3) | C11—C12—C13—C14 | −1.0 (6) |
| C3—C4—C5—C6 | −2.8 (5) | C12—C13—C14—C15 | 1.6 (6) |
| N2—C5—C6—C7 | −178.1 (3) | C11—C10—C15—C14 | 0.6 (5) |
| C4—C5—C6—C7 | 2.3 (5) | N1—C10—C15—C14 | 174.4 (3) |
| C5—C6—C7—C2 | −0.4 (5) | C13—C14—C15—C10 | −1.5 (6) |
This work was supported by the Natural Science Foundation of Shandong Province (No. Y2007B61) and the Natural Science Foundation of Weifang University.
Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
You, X.-L., Lu, C.-R., Zhang, Y. & Zhang, D.-C. (2004). Acta Cryst. C60, o693–o695.
![[Figure 1]](./lh2690fig1thm.gif)
Schiff base compounds have been used as fine chemicals and medical substrates and they are important ligands in coordination chemistry due to their ease of preparation and their ability to be modified both electronically and sterically. In this paper, the structure of the title compound, (I), is reported. The molecular structure of (I) is illustrated in Fig. 1. The bond lengths and angles in the title molecule are similar to the related compound 4-chloro-N-[4-(dimethylamino)benzylidene]aniline (You et al., 2004). The 4-(Dimethylamino)benzylidene system is nearly planar to within 0.035 (3) A°. 2-Chlorobenzenamine system is nearly planar to within 0.060 (3) A°. The dihedral angle between these two systems is 67.0 (2) °.