Acta Cryst. (2010). E66, o382 [ doi:10.1107/S160053681000125X ]
The asymmetric unit of the title compound, C17H19ClN2, contains two independent molecules which differ by a 180° flip in the orientation of the 4-chloroaniline unit with respect to the diethylaminobenzylidene unit [N=C-C-C = 10.0 (3) and -170.6 (2)°]. The dihedral angles between the two aromatic rings are 64.0 (1) and 66.5 (1)° in the two independent molecules.
A mixture of 4-(diethylamino)benzaldehyde (0.01 mol) and 4-chloroaniline (0.01 mol) in ethanol (10 ml) was refluxed for 2 h. After cooling, filtration and drying, the title compound was obtained. The title compound (10 mg) was dissolved in ethanol (15 ml) 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 in a difference map and then refined in a riding model, with C–H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C) and 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).
![[Figure 1]](./ci2995fig1thm.gif)
| Fig. 1. The two independent molecules of the title compound. Displacement ellipsoids are drawn at the 30% probability level. |
| C17H19ClN2 | F(000) = 1216 |
| Mr = 286.79 | Dx = 1.221 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1362 reflections |
| a = 20.153 (2) Å | θ = 2.4–21.4° |
| b = 8.7434 (7) Å | µ = 0.24 mm−1 |
| c = 20.1446 (19) Å | T = 293 K |
| β = 118.444 (2)° | Block, light yellow |
| V = 3121.0 (5) Å3 | 0.25 × 0.22 × 0.18 mm |
| Z = 8 |
| Bruker SMART CCD area-detector diffractometer | 5494 independent reflections |
| Radiation source: fine-focus sealed tube | 4266 reflections with I > 2σ(I) |
| graphite | Rint = 0.034 |
| ω scans | θmax = 25.0°, θmin = 3.0° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→23 |
| Tmin = 0.942, Tmax = 0.958 | k = −10→10 |
| 22416 measured reflections | l = −23→23 |
| 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.127 | H-atom parameters constrained |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.3803P] where P = (Fo2 + 2Fc2)/3 |
| 5494 reflections | (Δ/σ)max = 0.001 |
| 361 parameters | Δρmax = 0.25 e Å−3 |
| 0 restraints | Δρmin = −0.34 e Å−3 |
| C17H19ClN2 | V = 3121.0 (5) Å3 |
| Mr = 286.79 | Z = 8 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 20.153 (2) Å | µ = 0.24 mm−1 |
| b = 8.7434 (7) Å | T = 293 K |
| c = 20.1446 (19) Å | 0.25 × 0.22 × 0.18 mm |
| β = 118.444 (2)° |
| Bruker SMART CCD area-detector diffractometer | 5494 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4266 reflections with I > 2σ(I) |
| Tmin = 0.942, Tmax = 0.958 | Rint = 0.034 |
| 22416 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.127 | Δρmax = 0.25 e Å−3 |
| S = 1.07 | Δρmin = −0.34 e Å−3 |
| 5494 reflections | Absolute structure: ? |
| 361 parameters | Flack parameter: ? |
| 0 restraints | 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 | ||
| Cl2 | 0.85148 (4) | −0.53996 (7) | 0.76082 (4) | 0.0984 (2) | |
| Cl1 | 0.64613 (4) | 1.53729 (7) | 0.41511 (4) | 0.1002 (2) | |
| N2 | 0.59641 (9) | 1.07076 (17) | 0.18309 (8) | 0.0637 (4) | |
| N3 | 0.90381 (8) | 0.57265 (16) | 0.41592 (8) | 0.0619 (4) | |
| C7 | 0.58844 (9) | 0.83306 (19) | 0.07682 (9) | 0.0562 (4) | |
| H7A | 0.5731 | 0.9299 | 0.0560 | 0.067* | |
| C5 | 0.60395 (9) | 0.56348 (18) | 0.05880 (9) | 0.0530 (4) | |
| C23 | 0.91666 (10) | 0.30238 (19) | 0.44633 (10) | 0.0581 (4) | |
| H23A | 0.9321 | 0.2837 | 0.4103 | 0.070* | |
| C6 | 0.58355 (9) | 0.71363 (19) | 0.03069 (9) | 0.0567 (4) | |
| H6A | 0.5664 | 0.7319 | −0.0204 | 0.068* | |
| N4 | 0.90566 (9) | −0.05533 (17) | 0.58706 (9) | 0.0659 (4) | |
| C24 | 0.91207 (10) | 0.18314 (19) | 0.48779 (9) | 0.0583 (4) | |
| H24A | 0.9252 | 0.0855 | 0.4798 | 0.070* | |
| C22 | 0.89856 (9) | 0.45309 (18) | 0.45679 (9) | 0.0522 (4) | |
| C28 | 0.88144 (10) | 0.0793 (2) | 0.58554 (9) | 0.0593 (4) | |
| H28A | 0.8577 | 0.0992 | 0.6145 | 0.071* | |
| N1 | 0.59608 (9) | 0.44244 (16) | 0.01260 (9) | 0.0627 (4) | |
| C11 | 0.62332 (9) | 0.9374 (2) | 0.20476 (10) | 0.0568 (4) | |
| H11A | 0.6495 | 0.9186 | 0.2564 | 0.068* | |
| C25 | 0.88817 (9) | 0.20400 (19) | 0.54188 (9) | 0.0559 (4) | |
| C27 | 0.87455 (10) | 0.47377 (19) | 0.51171 (10) | 0.0585 (4) | |
| H27A | 0.8619 | 0.5712 | 0.5205 | 0.070* | |
| C8 | 0.61580 (9) | 0.81317 (19) | 0.15426 (9) | 0.0539 (4) | |
| C10 | 0.63215 (10) | 0.5445 (2) | 0.13724 (10) | 0.0612 (4) | |
| H10A | 0.6474 | 0.4480 | 0.1585 | 0.073* | |
| C12 | 0.61080 (10) | 1.18249 (19) | 0.23937 (9) | 0.0564 (4) | |
| C26 | 0.86968 (10) | 0.3532 (2) | 0.55194 (10) | 0.0609 (4) | |
| H26A | 0.8534 | 0.3708 | 0.5874 | 0.073* | |
| C29 | 0.89088 (10) | −0.16858 (19) | 0.62846 (9) | 0.0571 (4) | |
| C9 | 0.63739 (10) | 0.6647 (2) | 0.18232 (10) | 0.0609 (4) | |
| H9A | 0.6560 | 0.6476 | 0.2337 | 0.073* | |
| C15 | 0.63294 (11) | 1.4018 (2) | 0.34658 (11) | 0.0645 (5) | |
| C34 | 0.95037 (10) | −0.25322 (19) | 0.68199 (11) | 0.0628 (5) | |
| H34A | 0.9991 | −0.2339 | 0.6903 | 0.075* | |
| C32 | 0.86616 (10) | −0.3967 (2) | 0.70916 (10) | 0.0625 (4) | |
| C17 | 0.68257 (10) | 1.2175 (2) | 0.29554 (11) | 0.0669 (5) | |
| H17A | 0.7238 | 1.1663 | 0.2972 | 0.080* | |
| C16 | 0.69412 (11) | 1.3272 (2) | 0.34924 (12) | 0.0704 (5) | |
| H16A | 0.7427 | 1.3504 | 0.3867 | 0.084* | |
| C14 | 0.56102 (11) | 1.3704 (2) | 0.29018 (12) | 0.0730 (5) | |
| H14A | 0.5199 | 1.4220 | 0.2885 | 0.088* | |
| C33 | 0.93858 (10) | −0.3652 (2) | 0.72303 (11) | 0.0660 (5) | |
| H33A | 0.9792 | −0.4194 | 0.7598 | 0.079* | |
| C2 | 0.61471 (11) | 0.2868 (2) | 0.04203 (12) | 0.0709 (5) | |
| H2B | 0.5867 | 0.2156 | 0.0012 | 0.085* | |
| H2C | 0.5982 | 0.2725 | 0.0796 | 0.085* | |
| C13 | 0.55034 (10) | 1.2624 (2) | 0.23647 (11) | 0.0674 (5) | |
| H13A | 0.5019 | 1.2430 | 0.1977 | 0.081* | |
| C30 | 0.81858 (10) | −0.2037 (2) | 0.61520 (11) | 0.0696 (5) | |
| H30A | 0.7778 | −0.1496 | 0.5787 | 0.084* | |
| C4 | 0.57312 (12) | 0.4657 (2) | −0.06713 (11) | 0.0720 (5) | |
| H4B | 0.5317 | 0.5382 | −0.0878 | 0.086* | |
| H4C | 0.5546 | 0.3696 | −0.0936 | 0.086* | |
| C19 | 0.88835 (11) | 0.72995 (19) | 0.42921 (12) | 0.0699 (5) | |
| H19A | 0.9164 | 0.7989 | 0.4141 | 0.084* | |
| H19B | 0.9068 | 0.7438 | 0.4829 | 0.084* | |
| C21 | 0.92008 (12) | 0.5464 (2) | 0.35369 (12) | 0.0730 (5) | |
| H21A | 0.9627 | 0.4772 | 0.3705 | 0.088* | |
| H21B | 0.9347 | 0.6427 | 0.3405 | 0.088* | |
| C31 | 0.80608 (11) | −0.3174 (2) | 0.65510 (12) | 0.0714 (5) | |
| H31A | 0.7572 | −0.3402 | 0.6455 | 0.086* | |
| C20 | 0.85481 (14) | 0.4803 (3) | 0.28411 (12) | 0.0883 (7) | |
| H20A | 0.8693 | 0.4669 | 0.2455 | 0.132* | |
| H20B | 0.8126 | 0.5488 | 0.2664 | 0.132* | |
| H20C | 0.8410 | 0.3832 | 0.2962 | 0.132* | |
| C3 | 0.63511 (14) | 0.5236 (3) | −0.08195 (13) | 0.0882 (7) | |
| H3A | 0.6160 | 0.5365 | −0.1353 | 0.132* | |
| H3B | 0.6758 | 0.4512 | −0.0630 | 0.132* | |
| H3C | 0.6531 | 0.6201 | −0.0570 | 0.132* | |
| C18 | 0.80592 (12) | 0.7741 (2) | 0.38778 (15) | 0.0933 (7) | |
| H18A | 0.8003 | 0.8782 | 0.3995 | 0.140* | |
| H18B | 0.7776 | 0.7081 | 0.4031 | 0.140* | |
| H18C | 0.7874 | 0.7642 | 0.3344 | 0.140* | |
| C1 | 0.69744 (13) | 0.2482 (3) | 0.07706 (15) | 0.0991 (8) | |
| H1A | 0.7053 | 0.1449 | 0.0954 | 0.149* | |
| H1B | 0.7257 | 0.3167 | 0.1182 | 0.149* | |
| H1C | 0.7141 | 0.2584 | 0.0398 | 0.149* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl2 | 0.1067 (5) | 0.0772 (4) | 0.1268 (5) | −0.0034 (3) | 0.0682 (4) | 0.0204 (3) |
| Cl1 | 0.1127 (5) | 0.0755 (4) | 0.1135 (5) | −0.0022 (3) | 0.0549 (4) | −0.0307 (3) |
| N2 | 0.0695 (9) | 0.0627 (9) | 0.0590 (9) | 0.0001 (7) | 0.0307 (8) | 0.0018 (7) |
| N3 | 0.0668 (9) | 0.0526 (8) | 0.0632 (9) | −0.0015 (6) | 0.0283 (8) | −0.0032 (7) |
| C7 | 0.0584 (10) | 0.0542 (9) | 0.0571 (10) | 0.0021 (7) | 0.0285 (8) | 0.0076 (7) |
| C5 | 0.0499 (9) | 0.0542 (9) | 0.0561 (9) | −0.0034 (7) | 0.0263 (8) | 0.0027 (7) |
| C23 | 0.0627 (10) | 0.0593 (10) | 0.0541 (9) | 0.0065 (8) | 0.0292 (8) | −0.0027 (8) |
| C6 | 0.0590 (10) | 0.0612 (10) | 0.0489 (9) | −0.0001 (7) | 0.0250 (8) | 0.0058 (8) |
| N4 | 0.0775 (10) | 0.0637 (9) | 0.0628 (9) | 0.0058 (7) | 0.0386 (8) | −0.0002 (7) |
| C24 | 0.0643 (10) | 0.0539 (9) | 0.0556 (10) | 0.0077 (7) | 0.0279 (8) | −0.0038 (7) |
| C22 | 0.0468 (8) | 0.0536 (9) | 0.0462 (9) | −0.0011 (7) | 0.0140 (7) | −0.0058 (7) |
| C28 | 0.0617 (10) | 0.0649 (11) | 0.0503 (9) | 0.0030 (8) | 0.0258 (8) | −0.0044 (8) |
| N1 | 0.0700 (9) | 0.0542 (8) | 0.0627 (9) | −0.0029 (6) | 0.0306 (8) | −0.0007 (7) |
| C11 | 0.0531 (9) | 0.0658 (11) | 0.0538 (10) | −0.0010 (8) | 0.0275 (8) | 0.0034 (8) |
| C25 | 0.0561 (9) | 0.0593 (10) | 0.0469 (9) | 0.0017 (7) | 0.0202 (8) | −0.0042 (7) |
| C27 | 0.0618 (10) | 0.0533 (9) | 0.0547 (10) | 0.0029 (7) | 0.0231 (8) | −0.0117 (8) |
| C8 | 0.0506 (9) | 0.0603 (10) | 0.0535 (9) | −0.0019 (7) | 0.0269 (8) | 0.0015 (7) |
| C10 | 0.0674 (11) | 0.0572 (10) | 0.0583 (10) | 0.0029 (8) | 0.0295 (9) | 0.0111 (8) |
| C12 | 0.0627 (10) | 0.0536 (9) | 0.0563 (10) | −0.0012 (7) | 0.0311 (8) | 0.0073 (7) |
| C26 | 0.0655 (10) | 0.0649 (11) | 0.0511 (9) | 0.0028 (8) | 0.0268 (8) | −0.0111 (8) |
| C29 | 0.0644 (10) | 0.0549 (9) | 0.0543 (9) | 0.0026 (8) | 0.0302 (8) | −0.0080 (7) |
| C9 | 0.0656 (10) | 0.0670 (11) | 0.0509 (9) | 0.0011 (8) | 0.0285 (8) | 0.0089 (8) |
| C15 | 0.0738 (12) | 0.0501 (9) | 0.0743 (12) | −0.0026 (8) | 0.0390 (10) | −0.0017 (8) |
| C34 | 0.0560 (10) | 0.0571 (10) | 0.0753 (12) | 0.0021 (8) | 0.0313 (9) | −0.0027 (9) |
| C32 | 0.0703 (11) | 0.0512 (9) | 0.0708 (11) | −0.0025 (8) | 0.0376 (10) | −0.0052 (8) |
| C17 | 0.0571 (10) | 0.0704 (11) | 0.0779 (12) | 0.0002 (8) | 0.0358 (10) | −0.0042 (10) |
| C16 | 0.0578 (10) | 0.0689 (12) | 0.0783 (13) | −0.0053 (8) | 0.0275 (10) | −0.0101 (10) |
| C14 | 0.0632 (11) | 0.0575 (11) | 0.0990 (15) | 0.0086 (8) | 0.0391 (11) | 0.0011 (10) |
| C33 | 0.0603 (10) | 0.0568 (10) | 0.0727 (12) | 0.0047 (8) | 0.0250 (9) | 0.0030 (9) |
| C2 | 0.0719 (12) | 0.0535 (10) | 0.0827 (13) | −0.0025 (8) | 0.0332 (10) | 0.0006 (9) |
| C13 | 0.0558 (10) | 0.0578 (10) | 0.0772 (12) | 0.0040 (8) | 0.0225 (9) | 0.0035 (9) |
| C30 | 0.0580 (11) | 0.0717 (12) | 0.0693 (12) | 0.0081 (9) | 0.0223 (9) | 0.0018 (9) |
| C4 | 0.0848 (13) | 0.0649 (11) | 0.0613 (11) | −0.0090 (9) | 0.0307 (10) | −0.0107 (9) |
| C19 | 0.0666 (11) | 0.0515 (10) | 0.0813 (13) | −0.0012 (8) | 0.0267 (10) | −0.0028 (9) |
| C21 | 0.0829 (13) | 0.0669 (12) | 0.0791 (13) | −0.0034 (9) | 0.0465 (11) | 0.0061 (10) |
| C31 | 0.0574 (10) | 0.0690 (12) | 0.0881 (14) | −0.0030 (9) | 0.0349 (10) | −0.0062 (10) |
| C20 | 0.1086 (18) | 0.0907 (15) | 0.0606 (12) | 0.0092 (12) | 0.0362 (12) | 0.0058 (11) |
| C3 | 0.1165 (19) | 0.0832 (14) | 0.0860 (16) | 0.0070 (13) | 0.0652 (15) | −0.0008 (12) |
| C18 | 0.0720 (13) | 0.0778 (14) | 0.1146 (18) | 0.0135 (10) | 0.0319 (13) | 0.0052 (13) |
| C1 | 0.0780 (15) | 0.0875 (16) | 0.1166 (19) | 0.0177 (12) | 0.0342 (14) | 0.0075 (14) |
| Cl2—C32 | 1.7415 (19) | C15—C16 | 1.373 (3) |
| Cl1—C15 | 1.7407 (19) | C15—C14 | 1.378 (3) |
| N2—C11 | 1.273 (2) | C34—C33 | 1.373 (2) |
| N2—C12 | 1.418 (2) | C34—H34A | 0.93 |
| N3—C22 | 1.366 (2) | C32—C31 | 1.370 (3) |
| N3—C21 | 1.457 (2) | C32—C33 | 1.377 (2) |
| N3—C19 | 1.463 (2) | C17—C16 | 1.380 (3) |
| C7—C6 | 1.370 (2) | C17—H17A | 0.93 |
| C7—C8 | 1.396 (2) | C16—H16A | 0.93 |
| C7—H7A | 0.93 | C14—C13 | 1.373 (3) |
| C5—N1 | 1.368 (2) | C14—H14A | 0.93 |
| C5—C6 | 1.411 (2) | C33—H33A | 0.93 |
| C5—C10 | 1.411 (2) | C2—C1 | 1.507 (3) |
| C23—C24 | 1.366 (2) | C2—H2B | 0.97 |
| C23—C22 | 1.410 (2) | C2—H2C | 0.97 |
| C23—H23A | 0.93 | C13—H13A | 0.93 |
| C6—H6A | 0.93 | C30—C31 | 1.375 (3) |
| N4—C28 | 1.269 (2) | C30—H30A | 0.93 |
| N4—C29 | 1.415 (2) | C4—C3 | 1.504 (3) |
| C24—C25 | 1.397 (2) | C4—H4B | 0.97 |
| C24—H24A | 0.93 | C4—H4C | 0.97 |
| C22—C27 | 1.414 (2) | C19—C18 | 1.511 (3) |
| C28—C25 | 1.447 (2) | C19—H19A | 0.97 |
| C28—H28A | 0.93 | C19—H19B | 0.97 |
| N1—C4 | 1.459 (2) | C21—C20 | 1.507 (3) |
| N1—C2 | 1.460 (2) | C21—H21A | 0.97 |
| C11—C8 | 1.446 (2) | C21—H21B | 0.97 |
| C11—H11A | 0.93 | C31—H31A | 0.93 |
| C25—C26 | 1.398 (2) | C20—H20A | 0.96 |
| C27—C26 | 1.361 (2) | C20—H20B | 0.96 |
| C27—H27A | 0.93 | C20—H20C | 0.96 |
| C8—C9 | 1.400 (2) | C3—H3A | 0.96 |
| C10—C9 | 1.360 (2) | C3—H3B | 0.96 |
| C10—H10A | 0.93 | C3—H3C | 0.96 |
| C12—C17 | 1.381 (3) | C18—H18A | 0.96 |
| C12—C13 | 1.381 (2) | C18—H18B | 0.96 |
| C26—H26A | 0.93 | C18—H18C | 0.96 |
| C29—C34 | 1.384 (2) | C1—H1A | 0.96 |
| C29—C30 | 1.385 (3) | C1—H1B | 0.96 |
| C9—H9A | 0.93 | C1—H1C | 0.96 |
| C11—N2—C12 | 117.75 (15) | C12—C17—H17A | 119.5 |
| C22—N3—C21 | 120.79 (14) | C15—C16—C17 | 119.11 (18) |
| C22—N3—C19 | 121.66 (16) | C15—C16—H16A | 120.4 |
| C21—N3—C19 | 117.42 (16) | C17—C16—H16A | 120.4 |
| C6—C7—C8 | 121.71 (15) | C13—C14—C15 | 119.69 (17) |
| C6—C7—H7A | 119.1 | C13—C14—H14A | 120.2 |
| C8—C7—H7A | 119.1 | C15—C14—H14A | 120.2 |
| N1—C5—C6 | 121.97 (15) | C34—C33—C32 | 119.40 (17) |
| N1—C5—C10 | 121.69 (15) | C34—C33—H33A | 120.3 |
| C6—C5—C10 | 116.33 (15) | C32—C33—H33A | 120.3 |
| C24—C23—C22 | 121.62 (16) | N1—C2—C1 | 114.34 (17) |
| C24—C23—H23A | 119.2 | N1—C2—H2B | 108.7 |
| C22—C23—H23A | 119.2 | C1—C2—H2B | 108.7 |
| C7—C6—C5 | 121.59 (15) | N1—C2—H2C | 108.7 |
| C7—C6—H6A | 119.2 | C1—C2—H2C | 108.7 |
| C5—C6—H6A | 119.2 | H2B—C2—H2C | 107.6 |
| C28—N4—C29 | 118.48 (15) | C14—C13—C12 | 120.69 (17) |
| C23—C24—C25 | 121.73 (15) | C14—C13—H13A | 119.7 |
| C23—C24—H24A | 119.1 | C12—C13—H13A | 119.7 |
| C25—C24—H24A | 119.1 | C31—C30—C29 | 121.10 (17) |
| N3—C22—C23 | 121.71 (16) | C31—C30—H30A | 119.4 |
| N3—C22—C27 | 121.83 (15) | C29—C30—H30A | 119.5 |
| C23—C22—C27 | 116.47 (16) | N1—C4—C3 | 114.07 (18) |
| N4—C28—C25 | 124.55 (17) | N1—C4—H4B | 108.7 |
| N4—C28—H28A | 117.7 | C3—C4—H4B | 108.7 |
| C25—C28—H28A | 117.7 | N1—C4—H4C | 108.7 |
| C5—N1—C4 | 120.95 (14) | C3—C4—H4C | 108.7 |
| C5—N1—C2 | 121.38 (15) | H4B—C4—H4C | 107.6 |
| C4—N1—C2 | 117.57 (15) | N3—C19—C18 | 114.41 (16) |
| N2—C11—C8 | 124.21 (16) | N3—C19—H19A | 108.7 |
| N2—C11—H11A | 117.9 | C18—C19—H19A | 108.7 |
| C8—C11—H11A | 117.9 | N3—C19—H19B | 108.7 |
| C24—C25—C26 | 116.71 (16) | C18—C19—H19B | 108.7 |
| C24—C25—C28 | 122.85 (15) | H19A—C19—H19B | 107.6 |
| C26—C25—C28 | 120.43 (16) | N3—C21—C20 | 113.96 (18) |
| C26—C27—C22 | 121.02 (15) | N3—C21—H21A | 108.8 |
| C26—C27—H27A | 119.5 | C20—C21—H21A | 108.8 |
| C22—C27—H27A | 119.5 | N3—C21—H21B | 108.8 |
| C7—C8—C9 | 116.62 (16) | C20—C21—H21B | 108.8 |
| C7—C8—C11 | 123.10 (15) | H21A—C21—H21B | 107.7 |
| C9—C8—C11 | 120.27 (15) | C32—C31—C30 | 119.47 (18) |
| C9—C10—C5 | 121.25 (16) | C32—C31—H31A | 120.3 |
| C9—C10—H10A | 119.4 | C30—C31—H31A | 120.3 |
| C5—C10—H10A | 119.4 | C21—C20—H20A | 109.5 |
| C17—C12—C13 | 118.74 (17) | C21—C20—H20B | 109.5 |
| C17—C12—N2 | 122.91 (16) | H20A—C20—H20B | 109.5 |
| C13—C12—N2 | 118.32 (16) | C21—C20—H20C | 109.5 |
| C27—C26—C25 | 122.45 (17) | H20A—C20—H20C | 109.5 |
| C27—C26—H26A | 118.8 | H20B—C20—H20C | 109.5 |
| C25—C26—H26A | 118.8 | C4—C3—H3A | 109.5 |
| C34—C29—C30 | 118.21 (17) | C4—C3—H3B | 109.5 |
| C34—C29—N4 | 119.08 (16) | H3A—C3—H3B | 109.5 |
| C30—C29—N4 | 122.63 (16) | C4—C3—H3C | 109.5 |
| C10—C9—C8 | 122.46 (16) | H3A—C3—H3C | 109.5 |
| C10—C9—H9A | 118.8 | H3B—C3—H3C | 109.5 |
| C8—C9—H9A | 118.8 | C19—C18—H18A | 109.5 |
| C16—C15—C14 | 120.64 (18) | C19—C18—H18B | 109.5 |
| C16—C15—Cl1 | 119.81 (15) | H18A—C18—H18B | 109.5 |
| C14—C15—Cl1 | 119.54 (15) | C19—C18—H18C | 109.5 |
| C33—C34—C29 | 121.09 (17) | H18A—C18—H18C | 109.5 |
| C33—C34—H34A | 119.5 | H18B—C18—H18C | 109.5 |
| C29—C34—H34A | 119.5 | C2—C1—H1A | 109.5 |
| C31—C32—C33 | 120.69 (18) | C2—C1—H1B | 109.5 |
| C31—C32—Cl2 | 120.11 (15) | H1A—C1—H1B | 109.5 |
| C33—C32—Cl2 | 119.20 (14) | C2—C1—H1C | 109.5 |
| C16—C17—C12 | 121.07 (17) | H1A—C1—H1C | 109.5 |
| C16—C17—H17A | 119.5 | H1B—C1—H1C | 109.5 |
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
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.
Yu, Y. Y., Zhao, G. L. & Wen, Y. H. (2007). Chin. J. Struct. Chem. 26, 1359–1362.
Schiff base compounds have been used as fine chemicals and medical substrates. They are important ligands in coordination chemistry due to their ease of preparation and can both electronically and sterically modified (Yu et al., 2007). In this paper, the crystal structure of the title compound is reported.
The asymmetric unit of the title compound consists of two independent molecules, as illustrated in Fig. 1. The two molecules differ by a 180° flip in the orientation of the 4-chloroaniline unit with respect to the diethylaminobenzylidene moiety. The N4—C28—C25—C24 and N2—C11—C8—C9 torsion angles are 10.0 (3)° and -170.6 (2)°, respectively. In the two independent molecules, the dihedral angles between the two aromatic rings are 64.0 (1)° and 66.5 (1) °, respectively. Bond lengths and angles are comparable to those observed for 4-chloro-N-[4-(dimethylamino)benzylidene]aniline (You et al., 2004).