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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2478.
Published online 2008 November 29. doi:  10.1107/S1600536808039391
PMCID: PMC2959977

4-Chloro-N-(3-phenyl­allyl­idene)aniline

Abstract

In the title mol­ecule, C15H12ClN, the C=N and C=C bond lengths are 1.273 (2) and 1.324 (2) Å, respectively. The two aromatic rings form a dihedral angle of 3.27 (3)°.

Related literature

For a related structure, see Pu (2008 [triangle]). For general background, see: Garnovskii et al. (1993 [triangle]); Anderson et al. (1997 [triangle]); Musie et al. (2001 [triangle]); Paul et al. (2002 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-o2478-scheme1.jpg

Experimental

Crystal data

  • C15H12ClN
  • M r = 241.71
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2478-efi1.jpg
  • a = 7.7333 (7) Å
  • b = 5.5957 (5) Å
  • c = 29.383 (3) Å
  • V = 1271.5 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 295 (2) K
  • 0.15 × 0.12 × 0.08 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.960, T max = 0.978
  • 6043 measured reflections
  • 2187 independent reflections
  • 2042 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.066
  • S = 1.05
  • 2187 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.09 e Å−3
  • Δρmin = −0.15 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1031 Friedel pairs
  • Flack parameter: 0.07 (5)

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039391/cv2477sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039391/cv2477Isup2.hkl

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

Acknowledgments

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y03–1–13).

supplementary crystallographic information

Comment

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Garnovskii et al., 1993; Anderson et al., 1997; Musie et al., 2001; Paul et al., 2002; Pu, 2008). In order to search for new Schiff-bases with higher bioactivity, the title compound (I) was synthesized and its crystal structure determined.

In (I) (Fig. 1), the bond lengths and angles are in good agreement with the expected values (Allen et al., 1987).

Experimental

The title compound was synthesized by the reaction of 4-Chloro-phenylamine (1 mmol, 127.6 mg) with 3-Phenyl-propenal(1 mmol, 132.2 mg) in ethanol(20 ml) under reflux conditions (338 K) for 5 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After five days yellow crystals suitable for X-ray diffraction study were obtained.

Refinement

All H atoms were placed in idealized positions (C—H = 0.93Å) and refined as riding atoms with Uiso(H) = 1.2Ueq(C).

Figures

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

Crystal data

C15H12ClNF000 = 504
Mr = 241.71Dx = 1.263 Mg m3
Orthorhombic, Pna21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3328 reflections
a = 7.7333 (7) Åθ = 2.7–27.2º
b = 5.5957 (5) ŵ = 0.28 mm1
c = 29.383 (3) ÅT = 295 (2) K
V = 1271.5 (2) Å3Block, yellow
Z = 40.15 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer2187 independent reflections
Radiation source: fine-focus sealed tube2042 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.016
T = 295(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −9→9
Tmin = 0.960, Tmax = 0.978k = −6→4
6043 measured reflectionsl = −32→35

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026  w = 1/[σ2(Fo2) + (0.0375P)2 + 0.0706P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.066(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.09 e Å3
2187 reflectionsΔρmin = −0.15 e Å3
154 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1031 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.07 (5)

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
Cl10.65759 (7)0.44278 (11)0.969692 (18)0.08065 (18)
N10.87735 (18)0.5317 (3)0.77774 (5)0.0522 (3)
C10.7249 (2)0.4739 (3)0.91350 (6)0.0509 (4)
C20.8238 (2)0.6663 (3)0.90138 (5)0.0535 (4)
H20.85550.77950.92300.064*
C30.8761 (2)0.6907 (3)0.85660 (5)0.0503 (4)
H30.94430.82030.84830.060*
C40.82813 (19)0.5241 (3)0.82396 (6)0.0430 (3)
C50.7294 (2)0.3300 (3)0.83740 (6)0.0483 (4)
H50.69840.21520.81600.058*
C60.6762 (2)0.3037 (3)0.88200 (6)0.0524 (4)
H60.60880.17370.89060.063*
C70.9240 (2)0.7278 (3)0.75959 (6)0.0499 (4)
H70.92530.86570.77730.060*
C80.9747 (2)0.7431 (3)0.71272 (5)0.0477 (3)
H80.96500.60670.69480.057*
C91.0343 (2)0.9406 (3)0.69352 (5)0.0504 (4)
H91.04251.07440.71220.060*
C101.0884 (2)0.9711 (3)0.64651 (5)0.0421 (3)
C111.1805 (2)1.1742 (3)0.63356 (5)0.0493 (4)
H111.20651.29010.65520.059*
C121.2339 (2)1.2059 (3)0.58897 (6)0.0541 (4)
H121.29601.34190.58100.065*
C131.1957 (2)1.0385 (3)0.55664 (6)0.0531 (4)
H131.23071.06080.52670.064*
C141.1043 (2)0.8352 (3)0.56881 (5)0.0505 (4)
H141.07910.72010.54700.061*
C151.0509 (2)0.8028 (3)0.61284 (5)0.0452 (3)
H150.98860.66640.62040.054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0921 (4)0.1047 (4)0.0451 (2)−0.0037 (3)0.0100 (2)0.0165 (3)
N10.0539 (8)0.0588 (8)0.0439 (8)−0.0028 (6)0.0035 (6)0.0003 (6)
C10.0462 (9)0.0647 (11)0.0417 (8)0.0070 (8)0.0009 (7)0.0096 (8)
C20.0597 (10)0.0562 (10)0.0448 (9)−0.0048 (8)−0.0048 (7)−0.0015 (8)
C30.0522 (9)0.0502 (9)0.0487 (9)−0.0114 (8)−0.0012 (7)0.0045 (8)
C40.0383 (7)0.0467 (8)0.0441 (8)0.0020 (6)−0.0021 (7)0.0021 (7)
C50.0484 (9)0.0431 (8)0.0535 (9)−0.0021 (7)0.0010 (7)−0.0011 (7)
C60.0496 (9)0.0503 (9)0.0573 (10)−0.0071 (7)0.0031 (8)0.0092 (8)
C70.0480 (8)0.0569 (9)0.0448 (8)0.0002 (7)−0.0011 (7)0.0019 (7)
C80.0464 (8)0.0556 (9)0.0412 (7)−0.0002 (7)−0.0005 (7)−0.0001 (6)
C90.0534 (9)0.0527 (9)0.0450 (8)−0.0019 (7)−0.0028 (7)−0.0021 (7)
C100.0392 (7)0.0449 (8)0.0423 (8)0.0034 (6)−0.0041 (6)0.0052 (6)
C110.0499 (9)0.0444 (8)0.0537 (9)−0.0028 (7)−0.0055 (7)0.0005 (7)
C120.0515 (10)0.0483 (9)0.0625 (11)−0.0021 (7)0.0037 (8)0.0143 (8)
C130.0553 (10)0.0565 (10)0.0477 (10)0.0064 (7)0.0035 (7)0.0099 (8)
C140.0584 (10)0.0500 (9)0.0432 (9)0.0057 (7)−0.0044 (7)−0.0017 (7)
C150.0481 (8)0.0426 (7)0.0449 (8)−0.0032 (7)−0.0052 (7)0.0041 (7)

Geometric parameters (Å, °)

Cl1—C11.7399 (17)C8—C91.324 (2)
N1—C71.273 (2)C8—H80.9300
N1—C41.411 (2)C9—C101.454 (2)
C1—C21.368 (2)C9—H90.9300
C1—C61.380 (3)C10—C111.394 (2)
C2—C31.383 (2)C10—C151.397 (2)
C2—H20.9300C11—C121.385 (2)
C3—C41.388 (2)C11—H110.9300
C3—H30.9300C12—C131.367 (3)
C4—C51.385 (2)C12—H120.9300
C5—C61.382 (2)C13—C141.386 (3)
C5—H50.9300C13—H130.9300
C6—H60.9300C14—C151.370 (2)
C7—C81.434 (2)C14—H140.9300
C7—H70.9300C15—H150.9300
C7—N1—C4120.37 (14)C9—C8—H8118.2
C2—C1—C6121.41 (16)C7—C8—H8118.2
C2—C1—Cl1119.54 (14)C8—C9—C10127.14 (15)
C6—C1—Cl1119.05 (14)C8—C9—H9116.4
C1—C2—C3119.25 (16)C10—C9—H9116.4
C1—C2—H2120.4C11—C10—C15117.55 (14)
C3—C2—H2120.4C11—C10—C9120.17 (14)
C2—C3—C4120.87 (15)C15—C10—C9122.27 (14)
C2—C3—H3119.6C12—C11—C10121.00 (15)
C4—C3—H3119.6C12—C11—H11119.5
C5—C4—C3118.49 (15)C10—C11—H11119.5
C5—C4—N1116.52 (14)C13—C12—C11120.35 (16)
C3—C4—N1124.95 (14)C13—C12—H12119.8
C6—C5—C4121.20 (15)C11—C12—H12119.8
C6—C5—H5119.4C12—C13—C14119.57 (15)
C4—C5—H5119.4C12—C13—H13120.2
C5—C6—C1118.77 (15)C14—C13—H13120.2
C5—C6—H6120.6C15—C14—C13120.39 (15)
C1—C6—H6120.6C15—C14—H14119.8
N1—C7—C8122.08 (15)C13—C14—H14119.8
N1—C7—H7119.0C14—C15—C10121.14 (14)
C8—C7—H7119.0C14—C15—H15119.4
C9—C8—C7123.66 (15)C10—C15—H15119.4
C6—C1—C2—C30.0 (3)N1—C7—C8—C9−175.51 (17)
Cl1—C1—C2—C3−179.67 (13)C7—C8—C9—C10179.94 (15)
C1—C2—C3—C40.6 (2)C8—C9—C10—C11−166.99 (16)
C2—C3—C4—C5−1.3 (2)C8—C9—C10—C1513.3 (3)
C2—C3—C4—N1−178.92 (16)C15—C10—C11—C12−0.6 (2)
C7—N1—C4—C5160.20 (15)C9—C10—C11—C12179.69 (15)
C7—N1—C4—C3−22.1 (2)C10—C11—C12—C130.5 (3)
C3—C4—C5—C61.3 (2)C11—C12—C13—C14−0.6 (3)
N1—C4—C5—C6179.18 (14)C12—C13—C14—C150.7 (2)
C4—C5—C6—C1−0.7 (2)C13—C14—C15—C10−0.7 (2)
C2—C1—C6—C50.1 (2)C11—C10—C15—C140.7 (2)
Cl1—C1—C6—C5179.73 (13)C9—C10—C15—C14−179.60 (15)
C4—N1—C7—C8−179.89 (14)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2477).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Anderson, O. P., Cour, A. L., Findeisen, M., Hennig, L., Simonsen, O., Taylor, L. & Toflund, H. (1997). J. Chem. Soc. Dalton Trans. pp. 111–120.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Garnovskii, A. D., Nivorozhkin, A. L. & Minki, V. I. (1993). Coord. Chem. Rev.126, 1–69.
  • Musie, G. T., Wei, M., Subramaniam, B. & Busch, D. H. (2001). Inorg. Chem.40, 3336–3341. [PubMed]
  • Paul, S., Barik, A. K., Peng, S. M. & Kar, S. K. (2002). Inorg. Chem.41, 5803–5809. [PubMed]
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