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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2319.
Published online 2008 November 13. doi:  10.1107/S1600536808036386
PMCID: PMC2960011

2-Chloro-N-[4-(dimethyl­amino)benzyl­idene]aniline

Abstract

In the title mol­ecule, C15H15ClN2, the dihedral angle between the aromatic is 64.1 (2)°.

Related literature

For a related compound, see: You et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2319-scheme1.jpg

Experimental

Crystal data

  • C15H15ClN2
  • M r = 258.74
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2319-efi1.jpg
  • a = 7.7301 (8) Å
  • b = 12.2016 (18) Å
  • c = 14.047 (2) Å
  • V = 1325.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 298 (2) K
  • 0.45 × 0.38 × 0.30 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.888, T max = 0.923
  • 5507 measured reflections
  • 2318 independent reflections
  • 1391 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.105
  • S = 1.02
  • 2318 reflections
  • 165 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.18 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1358 Friedel pairs
  • Flack parameter: −0.07 (10)

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036386/lh2690sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036386/lh2690Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Natural Science Foundation of Shandong Province (No. Y2007B61) and the Natural Science Foundation of Weifang University.

supplementary crystallographic information

Comment

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) °.

Experimental

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.

Refinement

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).

Figures

Fig. 1.
The molecular structure of (I), drawn with 30% probability ellipsoids.

Crystal data

C15H15ClN2F000 = 544
Mr = 258.74Dx = 1.297 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1182 reflections
a = 7.7301 (8) Åθ = 2.9–20.1º
b = 12.2016 (18) ŵ = 0.27 mm1
c = 14.047 (2) ÅT = 298 (2) K
V = 1325.0 (3) Å3Block, light yellow
Z = 40.45 × 0.38 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer2318 independent reflections
Radiation source: fine-focus sealed tube1391 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.054
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 1997)h = −9→9
Tmin = 0.888, Tmax = 0.923k = −14→13
5507 measured reflectionsl = −9→16

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045  w = 1/[σ2(Fo2) + (0.0377P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.18 e Å3
2318 reflectionsΔρmin = −0.18 e Å3
165 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1358 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: −0.07 (10)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl11.22788 (14)1.11816 (8)−0.13149 (7)0.0753 (4)
N10.9918 (4)0.9322 (2)−0.09661 (18)0.0513 (8)
N20.8770 (4)0.7449 (2)0.32629 (18)0.0555 (8)
C11.0238 (4)0.8391 (3)−0.0595 (2)0.0477 (9)
H11.07880.7861−0.09620.057*
C20.9776 (4)0.8127 (2)0.0381 (2)0.0436 (9)
C30.8837 (4)0.8839 (3)0.0949 (2)0.0460 (9)
H30.84390.94910.06860.055*
C40.8472 (5)0.8618 (3)0.1884 (2)0.0478 (9)
H40.78150.91120.22350.057*
C50.9077 (4)0.7656 (3)0.2319 (2)0.0441 (9)
C60.9993 (5)0.6920 (3)0.1744 (2)0.0498 (9)
H61.03790.62610.20020.060*
C71.0331 (5)0.7156 (3)0.0807 (2)0.0510 (10)
H71.09490.66520.04450.061*
C80.7854 (5)0.8221 (3)0.3849 (2)0.0719 (12)
H8A0.85280.88780.39130.108*
H8B0.76600.79080.44670.108*
H8C0.67630.83940.35590.108*
C90.9648 (5)0.6548 (3)0.3736 (2)0.0671 (11)
H9A0.93420.58700.34320.101*
H9B0.93050.65240.43930.101*
H9C1.08760.66540.36960.101*
C101.0315 (5)0.9502 (3)−0.1928 (2)0.0452 (9)
C111.1315 (4)1.0405 (3)−0.2197 (2)0.0481 (9)
C121.1594 (5)1.0664 (3)−0.3137 (2)0.0595 (10)
H121.22661.1269−0.32980.071*
C131.0873 (5)1.0020 (3)−0.3841 (3)0.0654 (11)
H131.10421.0197−0.44780.078*
C140.9911 (5)0.9125 (3)−0.3600 (3)0.0661 (11)
H140.94510.8682−0.40750.079*
C150.9612 (5)0.8869 (3)−0.2650 (2)0.0587 (10)
H150.89320.8266−0.24970.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0818 (8)0.0730 (7)0.0711 (6)−0.0204 (6)−0.0003 (6)−0.0069 (5)
N10.060 (2)0.0516 (17)0.0423 (16)−0.0012 (18)0.0060 (16)0.0035 (14)
N20.053 (2)0.069 (2)0.0440 (17)0.0048 (18)0.0025 (15)0.0064 (15)
C10.048 (3)0.050 (2)0.045 (2)−0.0014 (19)−0.0003 (19)−0.0074 (17)
C20.046 (2)0.0450 (19)0.0397 (19)−0.0033 (19)0.0012 (18)−0.0035 (16)
C30.049 (2)0.0394 (18)0.049 (2)0.0003 (19)−0.0047 (17)0.0001 (18)
C40.050 (2)0.048 (2)0.045 (2)0.0075 (17)0.0021 (18)−0.0034 (17)
C50.042 (2)0.052 (2)0.0386 (19)−0.0057 (18)−0.0011 (17)−0.0029 (18)
C60.057 (3)0.0407 (19)0.051 (2)0.005 (2)−0.003 (2)0.0055 (17)
C70.056 (3)0.049 (2)0.048 (2)0.0044 (19)0.0023 (19)−0.0053 (18)
C80.076 (3)0.095 (3)0.045 (2)0.004 (3)0.012 (2)−0.002 (2)
C90.062 (3)0.078 (3)0.061 (2)−0.007 (2)−0.004 (2)0.024 (2)
C100.047 (2)0.046 (2)0.043 (2)0.0044 (19)0.0025 (19)0.0001 (17)
C110.047 (2)0.050 (2)0.047 (2)0.0046 (19)0.0041 (19)0.0020 (17)
C120.058 (3)0.063 (2)0.058 (2)−0.002 (2)0.014 (2)0.009 (2)
C130.069 (3)0.081 (3)0.046 (2)0.019 (2)0.008 (2)0.008 (2)
C140.068 (3)0.080 (3)0.050 (2)0.007 (3)−0.006 (2)−0.007 (2)
C150.062 (3)0.057 (2)0.057 (2)−0.003 (2)0.000 (2)−0.001 (2)

Geometric parameters (Å, °)

Cl1—C111.728 (3)C7—H70.9300
N1—C11.274 (3)C8—H8A0.9600
N1—C101.403 (4)C8—H8B0.9600
N2—C51.371 (4)C8—H8C0.9600
N2—C81.438 (4)C9—H9A0.9600
N2—C91.453 (4)C9—H9B0.9600
C1—C21.453 (4)C9—H9C0.9600
C1—H10.9300C10—C151.385 (4)
C2—C31.385 (4)C10—C111.398 (4)
C2—C71.395 (4)C11—C121.376 (4)
C3—C41.369 (4)C12—C131.379 (5)
C3—H30.9300C12—H120.9300
C4—C51.404 (4)C13—C141.364 (5)
C4—H40.9300C13—H130.9300
C5—C61.400 (4)C14—C151.390 (4)
C6—C71.373 (4)C14—H140.9300
C6—H60.9300C15—H150.9300
?···??
C1—N1—C10119.4 (3)N2—C8—H8C109.5
C5—N2—C8121.2 (3)H8A—C8—H8C109.5
C5—N2—C9120.1 (3)H8B—C8—H8C109.5
C8—N2—C9117.6 (3)N2—C9—H9A109.5
N1—C1—C2122.5 (3)N2—C9—H9B109.5
N1—C1—H1118.8H9A—C9—H9B109.5
C2—C1—H1118.8N2—C9—H9C109.5
C3—C2—C7116.5 (3)H9A—C9—H9C109.5
C3—C2—C1122.2 (3)H9B—C9—H9C109.5
C7—C2—C1121.2 (3)C15—C10—C11117.3 (3)
C4—C3—C2122.5 (3)C15—C10—N1122.2 (3)
C4—C3—H3118.7C11—C10—N1120.2 (3)
C2—C3—H3118.7C12—C11—C10121.8 (3)
C3—C4—C5120.9 (3)C12—C11—Cl1119.7 (3)
C3—C4—H4119.6C10—C11—Cl1118.5 (3)
C5—C4—H4119.6C11—C12—C13119.6 (3)
N2—C5—C6121.8 (3)C11—C12—H12120.2
N2—C5—C4121.2 (3)C13—C12—H12120.2
C6—C5—C4117.0 (3)C14—C13—C12119.9 (3)
C7—C6—C5121.0 (3)C14—C13—H13120.0
C7—C6—H6119.5C12—C13—H13120.0
C5—C6—H6119.5C13—C14—C15120.6 (4)
C6—C7—C2122.1 (3)C13—C14—H14119.7
C6—C7—H7119.0C15—C14—H14119.7
C2—C7—H7119.0C10—C15—C14120.8 (3)
N2—C8—H8A109.5C10—C15—H15119.6
N2—C8—H8B109.5C14—C15—H15119.6
H8A—C8—H8B109.5
C10—N1—C1—C2−176.5 (3)C3—C2—C7—C6−1.0 (5)
N1—C1—C2—C35.2 (5)C1—C2—C7—C6176.2 (3)
N1—C1—C2—C7−171.9 (3)C1—N1—C10—C1558.8 (5)
C7—C2—C3—C40.5 (5)C1—N1—C10—C11−127.5 (4)
C1—C2—C3—C4−176.7 (3)C15—C10—C11—C120.1 (5)
C2—C3—C4—C51.4 (5)N1—C10—C11—C12−173.9 (3)
C8—N2—C5—C6178.9 (3)C15—C10—C11—Cl1−177.6 (2)
C9—N2—C5—C610.8 (5)N1—C10—C11—Cl18.4 (4)
C8—N2—C5—C4−1.6 (5)C10—C11—C12—C130.1 (5)
C9—N2—C5—C4−169.6 (3)Cl1—C11—C12—C13177.7 (3)
C3—C4—C5—N2177.6 (3)C11—C12—C13—C14−1.0 (6)
C3—C4—C5—C6−2.8 (5)C12—C13—C14—C151.6 (6)
N2—C5—C6—C7−178.1 (3)C11—C10—C15—C140.6 (5)
C4—C5—C6—C72.3 (5)N1—C10—C15—C14174.4 (3)
C5—C6—C7—C2−0.4 (5)C13—C14—C15—C10−1.5 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
?—?···?????

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2690).

References

  • 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. [PubMed]
  • You, X.-L., Lu, C.-R., Zhang, Y. & Zhang, D.-C. (2004). Acta Cryst. C60, o693–o695. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography