Acta Cryst. (2008). E64, o1793 [ doi:10.1107/S1600536808026111 ]
The title compound, C14H12ClNO, was prepared by the reaction of 4-methoxyaniline and 4-chlorobenzaldehyde in ethanol at 367 K. The molecule is almost planar, with a dihedral angle between the two benzene rings of 9.1 (2)° and an r.m.s. deviation from the mean plane through all non-H atoms in the molecule of 0.167 Å.
A mixture of 4-methoxyaniline 2.46 g (0.02 mol) and 4-chlorobenzaldehyde 2.8 g (0.02 mol) was stirred in ethanol (50 mL) at 367 K for 2 h, to give the title compound (3.9 g, yield 81%). Single crystals suitable for X-ray measurements were obtained by recrystallization from acetone and ethanol(1:1) at room temperature.
All H-atoms were positioned geometrically and refined using a riding model with d(C-H) = 0.93Å, Uiso=1.2Ueq(C) for aromatic and 0.96Å, Uiso = 1.5Ueq(C) for CH3 atoms.
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]](./sj2527fig1thm.gif)
| Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
| C14H12ClNO | F000 = 512 |
| Mr = 245.70 | Dx = 1.326 Mg m−3 |
| Orthorhombic, Pna21 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: P 2c -2n | Cell parameters from 2092 reflections |
| a = 6.1055 (9) Å | θ = 2.9–28.3º |
| b = 7.3392 (11) Å | µ = 0.29 mm−1 |
| c = 27.469 (4) Å | T = 293 (2) K |
| V = 1230.9 (3) Å3 | Block, yellow |
| Z = 4 | 0.20 × 0.15 × 0.11 mm |
| Bruker SMART CCD area-detector diffractometer | 2092 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.022 |
| Monochromator: graphite | θmax = 28.3º |
| T = 293(2) K | θmin = 2.9º |
| φ and ω scans | h = −8→4 |
| Absorption correction: none | k = −9→9 |
| 7232 measured reflections | l = −36→33 |
| 2806 independent reflections |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.0836P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.088 | (Δ/σ)max < 0.001 |
| S = 1.01 | Δρmax = 0.14 e Å−3 |
| 2806 reflections | Δρmin = −0.16 e Å−3 |
| 154 parameters | Extinction correction: none |
| 1 restraint | Absolute structure: Flack (1983), 1450 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: −0.01 (7) |
| Secondary atom site location: difference Fourier map |
| C14H12ClNO | V = 1230.9 (3) Å3 |
| Mr = 245.70 | Z = 4 |
| Orthorhombic, Pna21 | Mo Kα |
| a = 6.1055 (9) Å | µ = 0.29 mm−1 |
| b = 7.3392 (11) Å | T = 293 (2) K |
| c = 27.469 (4) Å | 0.20 × 0.15 × 0.11 mm |
| Bruker SMART CCD area-detector diffractometer | 2806 independent reflections |
| Absorption correction: none | 2092 reflections with I > 2σ(I) |
| 7232 measured reflections | Rint = 0.022 |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.088 | Δρmax = 0.14 e Å−3 |
| S = 1.01 | Δρmin = −0.16 e Å−3 |
| 2806 reflections | Absolute structure: Flack (1983), 1450 Friedel pairs |
| 154 parameters | Flack parameter: −0.01 (7) |
| 1 restraint |
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 | 0.77772 (12) | 0.00540 (10) | 0.23599 (3) | 0.0862 (2) | |
| O1 | −0.0611 (2) | −0.01368 (19) | 0.64134 (5) | 0.0560 (4) | |
| N1 | 0.2457 (3) | 0.0122 (2) | 0.45058 (6) | 0.0463 (4) | |
| C1 | −0.2589 (4) | 0.0731 (4) | 0.65469 (10) | 0.0750 (7) | |
| H1B | −0.2859 | 0.0539 | 0.6887 | 0.112* | |
| H1C | −0.3775 | 0.0230 | 0.6361 | 0.112* | |
| H1D | −0.2475 | 0.2014 | 0.6483 | 0.112* | |
| C2 | 0.0048 (3) | −0.0027 (2) | 0.59389 (7) | 0.0421 (4) | |
| C3 | 0.1994 (3) | −0.0915 (2) | 0.58341 (7) | 0.0446 (4) | |
| H3A | 0.2739 | −0.1522 | 0.6081 | 0.053* | |
| C4 | 0.2838 (3) | −0.0909 (3) | 0.53699 (7) | 0.0456 (4) | |
| H4A | 0.4144 | −0.1513 | 0.5305 | 0.055* | |
| C5 | 0.1737 (3) | 0.0005 (2) | 0.49944 (7) | 0.0395 (4) | |
| C6 | −0.0225 (3) | 0.0856 (3) | 0.51062 (6) | 0.0436 (4) | |
| H6A | −0.0996 | 0.1442 | 0.4860 | 0.052* | |
| C7 | −0.1074 (3) | 0.0862 (2) | 0.55747 (7) | 0.0451 (4) | |
| H7A | −0.2384 | 0.1458 | 0.5642 | 0.054* | |
| C8 | 0.4424 (3) | −0.0157 (2) | 0.43961 (7) | 0.0475 (5) | |
| H8A | 0.5407 | −0.0439 | 0.4644 | 0.057* | |
| C9 | 0.5235 (3) | −0.0060 (2) | 0.38958 (8) | 0.0456 (4) | |
| C10 | 0.3951 (4) | 0.0631 (3) | 0.35228 (7) | 0.0537 (5) | |
| H10A | 0.2559 | 0.1075 | 0.3592 | 0.064* | |
| C11 | 0.4712 (4) | 0.0666 (3) | 0.30525 (8) | 0.0595 (6) | |
| H11A | 0.3842 | 0.1133 | 0.2804 | 0.071* | |
| C12 | 0.6790 (4) | 0.0000 (3) | 0.29508 (8) | 0.0572 (6) | |
| C13 | 0.8091 (3) | −0.0666 (3) | 0.33165 (8) | 0.0579 (5) | |
| H13A | 0.9480 | −0.1115 | 0.3247 | 0.069* | |
| C14 | 0.7321 (3) | −0.0665 (3) | 0.37880 (7) | 0.0534 (5) | |
| H14A | 0.8221 | −0.1079 | 0.4038 | 0.064* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0943 (5) | 0.1126 (5) | 0.0517 (3) | −0.0069 (4) | 0.0194 (4) | −0.0127 (3) |
| O1 | 0.0570 (9) | 0.0702 (10) | 0.0409 (7) | 0.0069 (7) | 0.0025 (7) | −0.0003 (6) |
| N1 | 0.0453 (10) | 0.0487 (10) | 0.0448 (10) | 0.0027 (7) | −0.0005 (7) | −0.0006 (7) |
| C1 | 0.0614 (15) | 0.104 (2) | 0.0598 (14) | 0.0089 (13) | 0.0097 (11) | −0.0055 (13) |
| C2 | 0.0414 (9) | 0.0408 (9) | 0.0440 (10) | −0.0062 (7) | −0.0034 (9) | −0.0031 (8) |
| C3 | 0.0429 (9) | 0.0450 (10) | 0.0459 (11) | 0.0016 (8) | −0.0062 (8) | 0.0036 (8) |
| C4 | 0.0396 (10) | 0.0457 (10) | 0.0516 (11) | 0.0073 (8) | −0.0017 (8) | 0.0024 (8) |
| C5 | 0.0408 (10) | 0.0361 (9) | 0.0417 (9) | −0.0022 (7) | −0.0009 (7) | −0.0013 (7) |
| C6 | 0.0409 (10) | 0.0411 (10) | 0.0487 (11) | 0.0043 (8) | −0.0080 (8) | 0.0020 (8) |
| C7 | 0.0397 (10) | 0.0444 (9) | 0.0511 (11) | 0.0048 (8) | −0.0023 (8) | −0.0014 (8) |
| C8 | 0.0453 (11) | 0.0527 (11) | 0.0446 (10) | −0.0005 (9) | −0.0036 (9) | −0.0018 (9) |
| C9 | 0.0435 (10) | 0.0449 (10) | 0.0484 (10) | −0.0041 (8) | −0.0011 (9) | −0.0025 (8) |
| C10 | 0.0479 (11) | 0.0593 (12) | 0.0540 (12) | 0.0032 (10) | 0.0019 (9) | −0.0013 (9) |
| C11 | 0.0598 (14) | 0.0688 (14) | 0.0498 (12) | 0.0060 (11) | −0.0051 (10) | 0.0013 (9) |
| C12 | 0.0660 (14) | 0.0581 (13) | 0.0476 (12) | −0.0085 (11) | 0.0123 (10) | −0.0092 (10) |
| C13 | 0.0473 (12) | 0.0646 (13) | 0.0617 (14) | 0.0032 (10) | 0.0059 (10) | −0.0055 (11) |
| C14 | 0.0473 (12) | 0.0620 (13) | 0.0508 (12) | 0.0043 (9) | −0.0002 (9) | 0.0018 (9) |
| Cl1—C12 | 1.732 (2) | C6—C7 | 1.387 (2) |
| O1—C2 | 1.366 (2) | C6—H6A | 0.9300 |
| O1—C1 | 1.414 (3) | C7—H7A | 0.9300 |
| N1—C8 | 1.255 (2) | C8—C9 | 1.463 (3) |
| N1—C5 | 1.415 (3) | C8—H8A | 0.9300 |
| C1—H1B | 0.9600 | C9—C14 | 1.381 (3) |
| C1—H1C | 0.9600 | C9—C10 | 1.386 (3) |
| C1—H1D | 0.9600 | C10—C11 | 1.373 (3) |
| C2—C7 | 1.377 (3) | C10—H10A | 0.9300 |
| C2—C3 | 1.386 (2) | C11—C12 | 1.388 (3) |
| C3—C4 | 1.375 (2) | C11—H11A | 0.9300 |
| C3—H3A | 0.9300 | C12—C13 | 1.371 (3) |
| C4—C5 | 1.402 (3) | C13—C14 | 1.378 (3) |
| C4—H4A | 0.9300 | C13—H13A | 0.9300 |
| C5—C6 | 1.386 (3) | C14—H14A | 0.9300 |
| C2—O1—C1 | 118.19 (17) | C2—C7—H7A | 120.4 |
| C8—N1—C5 | 121.00 (17) | C6—C7—H7A | 120.4 |
| O1—C1—H1B | 109.5 | N1—C8—C9 | 122.78 (18) |
| O1—C1—H1C | 109.5 | N1—C8—H8A | 118.6 |
| H1B—C1—H1C | 109.5 | C9—C8—H8A | 118.6 |
| O1—C1—H1D | 109.5 | C14—C9—C10 | 118.7 (2) |
| H1B—C1—H1D | 109.5 | C14—C9—C8 | 119.87 (19) |
| H1C—C1—H1D | 109.5 | C10—C9—C8 | 121.40 (17) |
| O1—C2—C7 | 125.07 (16) | C11—C10—C9 | 120.7 (2) |
| O1—C2—C3 | 115.02 (17) | C11—C10—H10A | 119.6 |
| C7—C2—C3 | 119.91 (18) | C9—C10—H10A | 119.6 |
| C4—C3—C2 | 120.82 (17) | C10—C11—C12 | 119.5 (2) |
| C4—C3—H3A | 119.6 | C10—C11—H11A | 120.3 |
| C2—C3—H3A | 119.6 | C12—C11—H11A | 120.3 |
| C3—C4—C5 | 120.27 (17) | C13—C12—C11 | 120.5 (2) |
| C3—C4—H4A | 119.9 | C13—C12—Cl1 | 119.55 (17) |
| C5—C4—H4A | 119.9 | C11—C12—Cl1 | 119.92 (19) |
| C6—C5—C4 | 117.86 (18) | C12—C13—C14 | 119.42 (18) |
| C6—C5—N1 | 116.83 (16) | C12—C13—H13A | 120.3 |
| C4—C5—N1 | 125.31 (16) | C14—C13—H13A | 120.3 |
| C5—C6—C7 | 122.00 (17) | C13—C14—C9 | 121.1 (2) |
| C5—C6—H6A | 119.0 | C13—C14—H14A | 119.5 |
| C7—C6—H6A | 119.0 | C9—C14—H14A | 119.5 |
| C2—C7—C6 | 119.11 (17) |
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Deschamps, P., Kulkarni, P. P. & Sarkar, B. (2003). Inorg. Chem., 42, 7366-7368.
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Jian, F.-F., Zhuang, R.-R., Wang, K.-F., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o3198–o3199.
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Tarafder, M. T. H., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456-460.
Schiff bases have been used extensively as ligands in the field of coordination chemistry (Jian et al., 2006), and have antimicrobial (Tarafder et al., 2000) and anticancer applications (Deschamps et al., 2003). Additional recent interest in Schiff base compounds comes from their ability to form intramolecular hydrogen bonds by electron coupling between acid-base centers (Rozwadowski et al.,1999). We report here the synthesis and structure of the title Schiff base compound, I, Fig. 1.
The molecule is almost planar with a dihedral angle between the C2···C7 and C9···C13 benzene rings of 9.1 (2)° and an rms deviation from the meanplane through all non-hydrogen atoms in the molecule of 0.167. The C═N bond distance (1.255 (2) Å) is in reasonable agreement with that observed in a similar compound (Jian et al., 2006).