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Acta Cryst. (2008). E64, o726    [ doi:10.1107/S1600536808003802 ]

2-Benzyliminomethyl-4-chlorophenol

X. Zhang and Z. Li

Abstract top

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.

Comment top

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).

Related literature top

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

Experimental top

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 top

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)

Computing details top

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

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. Packing of the molecules viewed along the b axis.
2-Benzyliminomethyl-4-chlorophenol top
Crystal data top
C14H12ClNOF000 = 512
Mr = 245.70Dx = 1.311 Mg m−3
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 mm−1
β = 103.911 (2)ºT = 298 (2) K
V = 1244.9 (3) Å3Rod, yellow
Z = 40.52 × 0.38 × 0.11 mm
Data collection top
Bruker SMART APEX
diffractometer		2177 independent reflections
Radiation source: fine-focus sealed tube864 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.046
T = 298(2) Kθmax = 25.0º
φ 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 top
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 Å−3
154 parametersΔρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C14H12ClNOV = 1244.9 (3) Å3
Mr = 245.70Z = 4
Monoclinic, P21/cMo Kα
a = 14.3693 (18) ŵ = 0.29 mm−1
b = 6.0401 (8) ÅT = 298 (2) K
c = 14.777 (2) Å0.52 × 0.38 × 0.11 mm
β = 103.911 (2)º
Data collection top
Bruker SMART APEX
diffractometer		2177 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		864 reflections with I > 2σ(I)
Tmin = 0.864, Tmax = 0.969Rint = 0.046
5203 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045154 parameters
wR(F2) = 0.116H-atom parameters constrained
S = 0.98Δρmax = 0.15 e Å−3
2177 reflectionsΔρmin = −0.22 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.597 (4)148
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.597 (4)148
Acknowledgements top

The author thanks Baoji University of Arts and Sciences for support.

references
References top

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.

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.

Tarafder, M. T. H., Jin, K. T., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2002). Polyhedron, 21, 2547–2554.