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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o726.
Published online 2008 March 20. doi:  10.1107/S1600536808003802
PMCID: PMC2960935

2-Benzyl­imino­methyl-4-chloro­phenol

Abstract

The title compound, C14H12ClNO, is a Schiff base derived from the condensation of equimolar quanti­ties of 5-chloro­salicylaldehyde and 1-benzyl­amine. The mol­ecule has a trans configuration with respect to the imine C=N double bond. The N atom is involved in an intra­molecular O—H(...)N hydrogen bond.

Related literature

For related literature, see: Ali et al. (2002 [triangle]); Cukurovali et al. (2002 [triangle]); Tarafder et al. (2002 [triangle]).

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Object name is e-64-0o726-scheme1.jpg

Experimental

Crystal data

  • C14H12ClNO
  • M r = 245.70
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o726-efi1.jpg
  • a = 14.3693 (18) Å
  • b = 6.0401 (8) Å
  • c = 14.777 (2) Å
  • β = 103.911 (2)°
  • V = 1244.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 298 (2) K
  • 0.52 × 0.38 × 0.11 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.864, T max = 0.969
  • 5203 measured reflections
  • 2177 independent reflections
  • 864 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.116
  • S = 0.98
  • 2177 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 [triangle]); 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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003802/cs2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003802/cs2068Isup2.hkl

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

Acknowledgments

The authors thank Baoji University of Arts and Sciences for support.

supplementary crystallographic information

Comment

Schiff base compounds have been of great interest for many years. These compounds played important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures. These properties stimulated our interest in this field. The title compound was obtained as a new antipyrine Schiff base.

Its molecular structure and a crystal packing are illustrated in Figs.1 and 2, respectively. Atom N1 is a bridging N atom linking the two parts of the compound. The dihedral angle between the two phenyl rings is 72.91 (9) °. In the crystal structure, there exists an intramolecular O—H—N hydrogen bond involving hydroxyl atom O1 and imine atom N1 (Table 1).

Experimental

All reagents used were of analytical grade from commercial sources and used without further purification. 5-Chlorosalicylaldehyde (0.1 mmol, 15.65 mg) and 1-benzylamine (0.1 mmol, 10.7 mg) were dissolved in methanol (10 ml). The resulting solution was stirred for 30 min, filtered and the filtrate allowed to stand at room temperature. Yellow crystals of the title compound appeared after two weeks of slow evaporation of the solvent.

Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range 0.93–0.96 Å and Uiso(H) = 1.2Ueq or 1.5Ueq(C/O)

Figures

Fig. 1.
The structure of the title compound with 30% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii. The dotted line represent a hydrogen bond.
Fig. 2.
Packing of the molecules viewed along the b axis.

Crystal data

C14H12ClNOF000 = 512
Mr = 245.70Dx = 1.311 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
a = 14.3693 (18) ÅCell parameters from 877 reflections
b = 6.0401 (8) Åθ = 2.8–25.1º
c = 14.777 (2) ŵ = 0.29 mm1
β = 103.911 (2)ºT = 298 (2) K
V = 1244.9 (3) Å3Rod, yellow
Z = 40.52 × 0.38 × 0.11 mm

Data collection

Bruker SMART APEX diffractometer2177 independent reflections
Radiation source: fine-focus sealed tube864 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.046
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −17→17
Tmin = 0.864, Tmax = 0.969k = −7→6
5203 measured reflectionsl = −17→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.116  w = 1/[σ2(Fo2) + (0.0248P)2 + 0.4795P] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2177 reflectionsΔρmax = 0.15 e Å3
154 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
Cl10.24166 (8)0.1883 (2)0.07747 (9)0.1401 (6)
N10.6895 (2)0.0444 (5)0.2091 (2)0.0878 (10)
O10.60143 (16)−0.2928 (4)0.11796 (16)0.0884 (8)
H10.6468−0.22030.14780.133*
C10.6093 (3)0.1388 (6)0.1982 (2)0.0772 (11)
H1A0.60700.28030.22230.093*
C20.5198 (2)0.0337 (6)0.1488 (2)0.0580 (8)
C30.5196 (3)−0.1769 (6)0.1098 (2)0.0613 (9)
C40.4338 (3)−0.2717 (6)0.0612 (2)0.0738 (10)
H40.4337−0.41180.03500.089*
C50.3499 (3)−0.1585 (7)0.0520 (2)0.0769 (11)
H50.2927−0.22220.01940.092*
C60.3489 (3)0.0483 (7)0.0904 (2)0.0740 (10)
C70.4331 (3)0.1431 (6)0.1383 (2)0.0717 (10)
H70.43200.28310.16420.086*
C80.7753 (3)0.1670 (8)0.2583 (3)0.1196 (16)
H8A0.80640.08840.31470.143*
H8B0.75670.31210.27590.143*
C90.8432 (2)0.1917 (8)0.1974 (3)0.0717 (10)
C100.8429 (3)0.3790 (7)0.1443 (3)0.0875 (12)
H100.80020.49320.14690.105*
C110.9053 (3)0.3980 (8)0.0877 (3)0.1031 (15)
H110.90420.52480.05170.124*
C120.9683 (3)0.2347 (11)0.0834 (3)0.1099 (16)
H121.01100.25030.04540.132*
C130.9693 (3)0.0497 (9)0.1342 (4)0.1057 (15)
H131.0120−0.06400.13080.127*
C140.9075 (3)0.0294 (7)0.1905 (3)0.0904 (12)
H140.9091−0.09910.22550.108*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1065 (8)0.1452 (11)0.1546 (11)0.0485 (8)0.0038 (7)0.0075 (9)
N10.0742 (19)0.117 (3)0.075 (2)−0.030 (2)0.0236 (18)−0.004 (2)
O10.0883 (17)0.0730 (17)0.113 (2)0.0039 (14)0.0419 (15)−0.0134 (15)
C10.102 (3)0.080 (3)0.056 (2)−0.032 (3)0.030 (2)−0.014 (2)
C20.078 (2)0.051 (2)0.050 (2)−0.007 (2)0.0238 (18)0.0015 (18)
C30.078 (2)0.052 (2)0.062 (2)−0.002 (2)0.033 (2)0.0004 (19)
C40.096 (3)0.057 (2)0.078 (3)−0.015 (2)0.038 (2)−0.015 (2)
C50.084 (3)0.091 (3)0.055 (2)−0.016 (2)0.016 (2)−0.007 (2)
C60.082 (3)0.077 (3)0.063 (3)0.014 (2)0.017 (2)0.011 (2)
C70.102 (3)0.053 (2)0.061 (2)0.001 (2)0.023 (2)−0.0014 (19)
C80.092 (3)0.186 (5)0.086 (3)−0.059 (3)0.031 (3)−0.032 (3)
C90.065 (2)0.079 (3)0.068 (3)−0.016 (2)0.011 (2)−0.012 (2)
C100.072 (3)0.073 (3)0.111 (4)0.005 (2)0.011 (2)−0.004 (3)
C110.094 (3)0.099 (4)0.111 (4)−0.022 (3)0.015 (3)0.030 (3)
C120.079 (3)0.160 (5)0.096 (4)−0.018 (3)0.029 (3)−0.002 (4)
C130.096 (3)0.111 (4)0.105 (4)0.024 (3)0.013 (3)−0.021 (3)
C140.114 (3)0.074 (3)0.075 (3)−0.004 (3)0.007 (3)0.003 (2)

Geometric parameters (Å, °)

Cl1—C61.727 (3)C7—H70.9300
N1—C11.260 (4)C8—C91.485 (4)
N1—C81.471 (4)C8—H8A0.9700
O1—C31.349 (3)C8—H8B0.9700
O1—H10.8200C9—C141.368 (5)
C1—C21.462 (4)C9—C101.376 (5)
C1—H1A0.9300C10—C111.370 (5)
C2—C71.385 (4)C10—H100.9300
C2—C31.396 (4)C11—C121.351 (5)
C3—C41.392 (4)C11—H110.9300
C4—C51.365 (4)C12—C131.344 (5)
C4—H40.9300C12—H120.9300
C5—C61.373 (4)C13—C141.361 (5)
C5—H50.9300C13—H130.9300
C6—C71.372 (4)C14—H140.9300
C1—N1—C8117.9 (4)N1—C8—H8A109.6
C3—O1—H1109.5C9—C8—H8A109.6
N1—C1—C2122.4 (4)N1—C8—H8B109.6
N1—C1—H1A118.8C9—C8—H8B109.6
C2—C1—H1A118.8H8A—C8—H8B108.1
C7—C2—C3118.4 (3)C14—C9—C10117.2 (4)
C7—C2—C1120.6 (3)C14—C9—C8121.8 (5)
C3—C2—C1121.0 (3)C10—C9—C8121.0 (4)
O1—C3—C4118.5 (3)C11—C10—C9120.3 (4)
O1—C3—C2121.4 (3)C11—C10—H10119.9
C4—C3—C2120.1 (3)C9—C10—H10119.9
C5—C4—C3119.8 (3)C12—C11—C10120.8 (4)
C5—C4—H4120.1C12—C11—H11119.6
C3—C4—H4120.1C10—C11—H11119.6
C4—C5—C6120.8 (3)C13—C12—C11119.9 (5)
C4—C5—H5119.6C13—C12—H12120.1
C6—C5—H5119.6C11—C12—H12120.1
C7—C6—C5119.8 (3)C12—C13—C14119.7 (5)
C7—C6—Cl1120.4 (3)C12—C13—H13120.2
C5—C6—Cl1119.9 (3)C14—C13—H13120.2
C6—C7—C2121.1 (3)C13—C14—C9122.2 (4)
C6—C7—H7119.4C13—C14—H14118.9
C2—C7—H7119.4C9—C14—H14118.9
N1—C8—C9110.2 (3)
C8—N1—C1—C2178.8 (3)C3—C2—C7—C6−0.4 (5)
N1—C1—C2—C7180.0 (3)C1—C2—C7—C6178.5 (3)
N1—C1—C2—C3−1.2 (5)C1—N1—C8—C9−121.1 (4)
C7—C2—C3—O1−179.6 (3)N1—C8—C9—C14−84.3 (4)
C1—C2—C3—O11.5 (5)N1—C8—C9—C1094.8 (4)
C7—C2—C3—C40.4 (4)C14—C9—C10—C11−0.1 (5)
C1—C2—C3—C4−178.4 (3)C8—C9—C10—C11−179.2 (3)
O1—C3—C4—C5179.8 (3)C9—C10—C11—C12−0.5 (6)
C2—C3—C4—C5−0.2 (5)C10—C11—C12—C130.9 (7)
C3—C4—C5—C6−0.1 (5)C11—C12—C13—C14−0.9 (7)
C4—C5—C6—C70.2 (5)C12—C13—C14—C90.3 (6)
C4—C5—C6—Cl1179.8 (3)C10—C9—C14—C130.2 (5)
C5—C6—C7—C20.1 (5)C8—C9—C14—C13179.3 (3)
Cl1—C6—C7—C2−179.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.597 (4)148

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2068).

References

  • Ali, M. A., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Keat, T. B. & Ali, A. M. (2002). J. Inorg. Biochem. 92, 141-148. [PubMed]
  • Bruker (2000). SMART (Version 5.0) and SAINT (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cukurovali, A., Yilmaz, I., Özmen, H. & Ahmedzade, M. (2002). Transition Met. Chem. 27, 171-176.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tarafder, M. T. H., Jin, K. T., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2002). Polyhedron, 21, 2547-2554.

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