organic compounds
(E)-4-Chloro-2-{[4-(dimethylamino)benzylidene]amino}phenol
aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, Algeria
*Correspondence e-mail: king.ali@hotmail.fr
In the title aromatic Schiff base compound, C15H15ClN2O, the molecule exists in a trans conformation with respect to the C=N bond. The dihedral angle between the benzene rings is 14.49 (6)°. In the crystal, weak C—H⋯π interactions link molecules into supramolecular chains propagated along the a-axis direction.
Related literature
For the use of et al. (2002). For their use as biological, analytical, polymer and liquid crystalline materials, see: Tanaka & Shiraishi (2000). have been reported to show antibacterial (Jarrahpour & Khalili, 2006; Jarrahpour et al., 2004; El-masry et al., 2000), antifungal (More et al., 2001; Singh & Dash, 1988), anticancer (Desai et al., 2001; Phatak et al., 2000) and herbicidal activity (Samadhiya & Halve, 2001). For related structures, see: Akkurt et al. (2005, 2008).
in synthesis, see: AroraExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
10.1107/S1600536814008873/xu5785sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814008873/xu5785Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814008873/xu5785Isup3.cml
A mixture of 3,4-dimethoxyaniline (1 mmol) and 4-nitrobenzaldehyde (1 mmol) was added and heated to form a clear solution. To this a few drops of conc. H2SO4 was added as a catalyst and refluxed for 6 h. After cooling the solution, After stirring at 80°C for 20 min the formed precipitate was filtered off and washed with ice ethanol to give pure Schiff base as an yellow solid in an 80% yield. The crude product was dissolved in ethanol and two spoons of
were added. The mixture was filtered over celite® and the product was crystallized from ethyl acetate, yellow crystal was obtained after two weeks.Anisotropic thermal parameters were applied to all non hydrogen atoms. The organic hydrogen atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.96 Å (methyl) and N—H = 0.86 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) for the others.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. View of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. |
C15H15ClN2O | Z = 8 |
Mr = 274.74 | F(000) = 1152 |
Orthorhombic, Pbca | Dx = 1.347 Mg m−3 |
Hall symbol: -P 2ac 2ab | Mo Kα radiation, λ = 0.71073 Å |
a = 7.411 (5) Å | µ = 0.28 mm−1 |
b = 12.314 (5) Å | T = 293 K |
c = 29.684 (5) Å | Block, yellow |
V = 2709 (2) Å3 | 0.03 × 0.02 × 0.01 mm |
Bruker APEXII CCD diffractometer | 1895 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.1°, θmin = 3.1° |
phi and ω scans | h = −8→8 |
14319 measured reflections | k = −13→14 |
2346 independent reflections | l = −33→35 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0321P)2 + 1.9647P] where P = (Fo2 + 2Fc2)/3 |
2346 reflections | (Δ/σ)max = 0.001 |
172 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C15H15ClN2O | V = 2709 (2) Å3 |
Mr = 274.74 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.411 (5) Å | µ = 0.28 mm−1 |
b = 12.314 (5) Å | T = 293 K |
c = 29.684 (5) Å | 0.03 × 0.02 × 0.01 mm |
Bruker APEXII CCD diffractometer | 1895 reflections with I > 2σ(I) |
14319 measured reflections | Rint = 0.028 |
2346 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.20 e Å−3 |
2346 reflections | Δρmin = −0.20 e Å−3 |
172 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
Cl01 | 0.50194 (10) | 0.14231 (6) | 0.23931 (2) | 0.0581 (2) | |
O002 | 0.7854 (3) | −0.17647 (13) | 0.11151 (6) | 0.0568 (6) | |
N1 | 0.6988 (2) | 0.01773 (14) | 0.07922 (6) | 0.0368 (6) | |
N2 | 0.7096 (3) | 0.22034 (16) | −0.12244 (6) | 0.0488 (7) | |
C1 | 0.7045 (4) | −0.1285 (2) | 0.18620 (8) | 0.0527 (9) | |
C2 | 0.6370 (4) | −0.0540 (2) | 0.21635 (8) | 0.0508 (9) | |
C3 | 0.5870 (3) | 0.04721 (19) | 0.20103 (7) | 0.0401 (7) | |
C4 | 0.6031 (3) | 0.07596 (18) | 0.15641 (7) | 0.0377 (7) | |
C5 | 0.6693 (3) | 0.00046 (17) | 0.12564 (7) | 0.0336 (6) | |
C6 | 0.7202 (3) | −0.10202 (19) | 0.14121 (7) | 0.0415 (8) | |
C7 | 0.6153 (3) | 0.09407 (18) | 0.05884 (7) | 0.0353 (7) | |
C8 | 0.6406 (3) | 0.12185 (17) | 0.01192 (7) | 0.0326 (7) | |
C9 | 0.5587 (3) | 0.21453 (18) | −0.00490 (7) | 0.0404 (7) | |
C10 | 0.5801 (3) | 0.24837 (19) | −0.04866 (7) | 0.0409 (7) | |
C11 | 0.6858 (3) | 0.18775 (17) | −0.07873 (7) | 0.0351 (7) | |
C12 | 0.7676 (3) | 0.09286 (18) | −0.06181 (7) | 0.0384 (7) | |
C13 | 0.7462 (3) | 0.06157 (17) | −0.01784 (7) | 0.0364 (7) | |
C14 | 0.6269 (4) | 0.3194 (2) | −0.13863 (8) | 0.0584 (10) | |
C15 | 0.7819 (4) | 0.1475 (2) | −0.15601 (7) | 0.0542 (9) | |
H1 | 0.73970 | −0.19690 | 0.19620 | 0.0630* | |
H02 | 0.78730 | −0.15000 | 0.08620 | 0.0850* | |
H2 | 0.62520 | −0.07170 | 0.24670 | 0.0610* | |
H4 | 0.57000 | 0.14510 | 0.14690 | 0.0450* | |
H7 | 0.53250 | 0.13460 | 0.07530 | 0.0420* | |
H9 | 0.48630 | 0.25550 | 0.01420 | 0.0480* | |
H10 | 0.52420 | 0.31180 | −0.05840 | 0.0490* | |
H12 | 0.83780 | 0.05050 | −0.08090 | 0.0460* | |
H13 | 0.80310 | −0.00110 | −0.00770 | 0.0440* | |
H14A | 0.65710 | 0.32970 | −0.16980 | 0.0870* | |
H14B | 0.67050 | 0.37980 | −0.12130 | 0.0870* | |
H14C | 0.49830 | 0.31420 | −0.13550 | 0.0870* | |
H15A | 0.78840 | 0.18430 | −0.18450 | 0.0810* | |
H15B | 0.70480 | 0.08520 | −0.15870 | 0.0810* | |
H15C | 0.90060 | 0.12460 | −0.14720 | 0.0810* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl01 | 0.0648 (4) | 0.0729 (5) | 0.0366 (3) | 0.0025 (4) | 0.0062 (3) | −0.0031 (3) |
O002 | 0.0736 (13) | 0.0446 (10) | 0.0522 (10) | 0.0160 (9) | −0.0035 (9) | 0.0047 (8) |
N1 | 0.0422 (11) | 0.0344 (10) | 0.0337 (9) | −0.0028 (9) | −0.0004 (8) | 0.0040 (8) |
N2 | 0.0689 (15) | 0.0490 (12) | 0.0285 (9) | −0.0023 (11) | 0.0040 (10) | −0.0006 (9) |
C1 | 0.0608 (17) | 0.0469 (14) | 0.0504 (14) | 0.0015 (13) | −0.0106 (13) | 0.0188 (12) |
C2 | 0.0555 (16) | 0.0617 (16) | 0.0351 (12) | −0.0045 (14) | −0.0066 (11) | 0.0156 (12) |
C3 | 0.0366 (12) | 0.0506 (14) | 0.0330 (11) | −0.0062 (11) | −0.0021 (10) | 0.0026 (10) |
C4 | 0.0390 (13) | 0.0384 (12) | 0.0357 (11) | −0.0042 (10) | −0.0017 (10) | 0.0077 (10) |
C5 | 0.0324 (11) | 0.0345 (11) | 0.0340 (11) | −0.0054 (10) | −0.0033 (9) | 0.0059 (9) |
C6 | 0.0397 (13) | 0.0415 (13) | 0.0432 (13) | 0.0000 (11) | −0.0065 (11) | 0.0053 (11) |
C7 | 0.0362 (12) | 0.0368 (12) | 0.0328 (11) | −0.0023 (10) | 0.0025 (10) | −0.0003 (9) |
C8 | 0.0335 (12) | 0.0328 (11) | 0.0315 (11) | −0.0023 (10) | 0.0001 (9) | 0.0001 (9) |
C9 | 0.0445 (14) | 0.0431 (13) | 0.0335 (11) | 0.0100 (11) | 0.0058 (10) | −0.0018 (10) |
C10 | 0.0485 (14) | 0.0392 (13) | 0.0350 (11) | 0.0100 (11) | −0.0009 (10) | 0.0035 (10) |
C11 | 0.0392 (13) | 0.0359 (12) | 0.0303 (11) | −0.0084 (10) | −0.0005 (9) | −0.0024 (9) |
C12 | 0.0437 (13) | 0.0360 (12) | 0.0356 (11) | −0.0011 (11) | 0.0060 (10) | −0.0084 (10) |
C13 | 0.0408 (13) | 0.0287 (11) | 0.0398 (12) | −0.0003 (10) | −0.0008 (10) | 0.0006 (9) |
C14 | 0.084 (2) | 0.0552 (16) | 0.0359 (13) | −0.0045 (15) | −0.0009 (13) | 0.0107 (11) |
C15 | 0.0613 (17) | 0.0677 (17) | 0.0335 (12) | −0.0105 (14) | 0.0077 (12) | −0.0066 (12) |
Cl01—C3 | 1.749 (3) | C10—C11 | 1.403 (3) |
O002—C6 | 1.361 (3) | C11—C12 | 1.409 (3) |
O002—H02 | 0.8200 | C12—C13 | 1.370 (3) |
N1—C7 | 1.278 (3) | C1—H1 | 0.9300 |
N1—C5 | 1.411 (3) | C2—H2 | 0.9300 |
N2—C11 | 1.370 (3) | C4—H4 | 0.9300 |
N2—C15 | 1.444 (3) | C7—H7 | 0.9300 |
N2—C14 | 1.447 (3) | C9—H9 | 0.9300 |
C1—C6 | 1.380 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.376 (4) | C12—H12 | 0.9300 |
C2—C3 | 1.378 (4) | C13—H13 | 0.9300 |
C3—C4 | 1.376 (3) | C14—H14A | 0.9600 |
C4—C5 | 1.393 (3) | C14—H14B | 0.9600 |
C5—C6 | 1.396 (3) | C14—H14C | 0.9600 |
C7—C8 | 1.446 (3) | C15—H15A | 0.9600 |
C8—C13 | 1.394 (3) | C15—H15B | 0.9600 |
C8—C9 | 1.386 (3) | C15—H15C | 0.9600 |
C9—C10 | 1.373 (3) | ||
Cl01···H15Ai | 3.1200 | H4···O002ii | 2.6600 |
Cl01···H1ii | 3.0400 | H7···C4 | 2.5700 |
Cl01···H14Aiii | 2.9500 | H7···H4 | 2.1500 |
O002···N1 | 2.655 (3) | H7···H9 | 2.3700 |
O002···C10iv | 3.406 (4) | H7···O002ii | 2.9000 |
O002···C7v | 3.312 (4) | H9···H7 | 2.3700 |
O002···H14Civ | 2.7900 | H9···C8i | 3.0700 |
O002···H15Cvi | 2.6400 | H9···C11i | 3.0200 |
O002···H4v | 2.6600 | H9···C12i | 2.8500 |
O002···H7v | 2.9000 | H9···C13i | 2.8700 |
N1···O002 | 2.655 (3) | H10···C14 | 2.5000 |
N1···H02 | 2.1800 | H10···H14B | 2.3200 |
N1···H13 | 2.7000 | H10···H14C | 2.3000 |
C7···C13iv | 3.512 (4) | H12···C15 | 2.5600 |
C7···O002ii | 3.312 (4) | H12···H15B | 2.5500 |
C10···O002iv | 3.406 (4) | H12···H15C | 2.2200 |
C13···C7iv | 3.512 (4) | H12···H14Bv | 2.4200 |
C2···H15Biv | 3.0800 | H13···N1 | 2.7000 |
C3···H15Biv | 2.9900 | H14A···H15A | 2.0800 |
C4···H15Biv | 3.0200 | H14A···Cl01ix | 2.9500 |
C4···H7 | 2.5700 | H14B···C10 | 2.7800 |
C6···H15Cvi | 2.8300 | H14B···H10 | 2.3200 |
C6···H14Civ | 3.0800 | H14B···H12ii | 2.4200 |
C7···H4 | 2.7100 | H14C···C10 | 2.7700 |
C8···H9vii | 3.0700 | H14C···H10 | 2.3000 |
C10···H14B | 2.7800 | H14C···O002iv | 2.7900 |
C10···H14C | 2.7700 | H14C···C6iv | 3.0800 |
C11···H9vii | 3.0200 | H15A···H14A | 2.0800 |
C12···H15B | 2.9200 | H15A···H2x | 2.5500 |
C12···H9vii | 2.8500 | H15A···Cl01vii | 3.1200 |
C12···H15C | 2.7500 | H15B···C12 | 2.9200 |
C13···H9vii | 2.8700 | H15B···H12 | 2.5500 |
C14···H10 | 2.5000 | H15B···C2iv | 3.0800 |
C15···H12 | 2.5600 | H15B···C3iv | 2.9900 |
H1···Cl01v | 3.0400 | H15B···C4iv | 3.0200 |
H02···N1 | 2.1800 | H15C···C12 | 2.7500 |
H2···H15Aviii | 2.5500 | H15C···H12 | 2.2200 |
H4···C7 | 2.7100 | H15C···O002vi | 2.6400 |
H4···H7 | 2.1500 | H15C···C6vi | 2.8300 |
C6—O002—H02 | 109.00 | C2—C1—H1 | 120.00 |
C5—N1—C7 | 119.88 (18) | C6—C1—H1 | 120.00 |
C11—N2—C14 | 120.47 (19) | C1—C2—H2 | 120.00 |
C14—N2—C15 | 116.85 (18) | C3—C2—H2 | 120.00 |
C11—N2—C15 | 121.31 (19) | C3—C4—H4 | 120.00 |
C2—C1—C6 | 120.2 (2) | C5—C4—H4 | 120.00 |
C1—C2—C3 | 119.1 (2) | N1—C7—H7 | 118.00 |
Cl01—C3—C4 | 118.96 (18) | C8—C7—H7 | 118.00 |
C2—C3—C4 | 121.8 (2) | C8—C9—H9 | 119.00 |
Cl01—C3—C2 | 119.23 (17) | C10—C9—H9 | 119.00 |
C3—C4—C5 | 119.3 (2) | C9—C10—H10 | 120.00 |
N1—C5—C4 | 126.47 (19) | C11—C10—H10 | 120.00 |
N1—C5—C6 | 114.69 (18) | C11—C12—H12 | 119.00 |
C4—C5—C6 | 118.79 (19) | C13—C12—H12 | 119.00 |
O002—C6—C5 | 119.38 (19) | C8—C13—H13 | 119.00 |
C1—C6—C5 | 120.8 (2) | C12—C13—H13 | 119.00 |
O002—C6—C1 | 119.9 (2) | N2—C14—H14A | 109.00 |
N1—C7—C8 | 124.6 (2) | N2—C14—H14B | 109.00 |
C7—C8—C13 | 123.85 (19) | N2—C14—H14C | 109.00 |
C9—C8—C13 | 117.13 (19) | H14A—C14—H14B | 110.00 |
C7—C8—C9 | 119.01 (19) | H14A—C14—H14C | 109.00 |
C8—C9—C10 | 122.7 (2) | H14B—C14—H14C | 110.00 |
C9—C10—C11 | 120.3 (2) | N2—C15—H15A | 109.00 |
N2—C11—C10 | 121.3 (2) | N2—C15—H15B | 109.00 |
N2—C11—C12 | 121.7 (2) | N2—C15—H15C | 110.00 |
C10—C11—C12 | 117.05 (19) | H15A—C15—H15B | 109.00 |
C11—C12—C13 | 121.5 (2) | H15A—C15—H15C | 109.00 |
C8—C13—C12 | 121.3 (2) | H15B—C15—H15C | 109.00 |
C7—N1—C5—C4 | −21.8 (3) | N1—C5—C6—O002 | −2.4 (3) |
C7—N1—C5—C6 | 161.0 (2) | N1—C5—C6—C1 | 177.8 (2) |
C5—N1—C7—C8 | 177.4 (2) | C4—C5—C6—O002 | −179.9 (2) |
C14—N2—C11—C10 | 0.6 (3) | C4—C5—C6—C1 | 0.3 (3) |
C14—N2—C11—C12 | −178.7 (2) | N1—C7—C8—C9 | −172.2 (2) |
C15—N2—C11—C10 | −165.6 (2) | N1—C7—C8—C13 | 6.7 (4) |
C15—N2—C11—C12 | 15.1 (3) | C7—C8—C9—C10 | 178.1 (2) |
C6—C1—C2—C3 | −0.5 (4) | C13—C8—C9—C10 | −0.9 (3) |
C2—C1—C6—O002 | −179.4 (2) | C7—C8—C13—C12 | −178.9 (2) |
C2—C1—C6—C5 | 0.4 (4) | C9—C8—C13—C12 | −0.1 (3) |
C1—C2—C3—Cl01 | −179.8 (2) | C8—C9—C10—C11 | 1.1 (3) |
C1—C2—C3—C4 | −0.2 (4) | C9—C10—C11—N2 | −179.7 (2) |
Cl01—C3—C4—C5 | −179.48 (17) | C9—C10—C11—C12 | −0.4 (3) |
C2—C3—C4—C5 | 0.9 (4) | N2—C11—C12—C13 | 178.8 (2) |
C3—C4—C5—N1 | −178.1 (2) | C10—C11—C12—C13 | −0.5 (3) |
C3—C4—C5—C6 | −1.0 (3) | C11—C12—C13—C8 | 0.8 (3) |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x+3/2, y+1/2, z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y, −z; (v) −x+3/2, y−1/2, z; (vi) −x+2, −y, −z; (vii) x+1/2, −y+1/2, −z; (viii) −x+3/2, −y, z+1/2; (ix) x, −y+1/2, z−1/2; (x) −x+3/2, −y, z−1/2. |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Cg2i | 0.93 | 2.70 | 3.533 (3) | 150 |
C15—H15B···Cg1iv | 0.96 | 2.76 | 3.581 (4) | 142 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (iv) −x+1, −y, −z. |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···Cg2i | 0.93 | 2.70 | 3.533 (3) | 150 |
C15—H15B···Cg1ii | 0.96 | 2.76 | 3.581 (4) | 142 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x+1, −y, −z. |
Acknowledgements
We thank all researchers of the CHEMS Research Unit, University of Constantine 1, Algeria, for their valuable assistance. The authors thank the MESRS (Algeria) for financial support.
References
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Schiff bases are widely used for synthetic purposes both by organic and inorganic chemists (Arora et al., 2002) and have uses as biological, analytical, polymer and liquid crystalline materials (Tanaka & Shiraishi, 2000). Schiff bases are reported to show a variety of biological activities such as antibacterial (Jarrahpour & Khalili, 2006; Jarrahpour et al., 2004; El-masry et al., 2000), antifungal (More et al., 2001; Singh & Dash, 1988), anticancer (Desai et al., 2001; Phatak et al., 2000) and herbicidal activities (Samadhiya & Halve, 2001). As an extension of our work on Schiff bases, we report here the crystal structure of the title compound (I).