2-Benzyl­imino­methyl-4-chloro­phenol

Zhang, X.; Li, Z.

doi:10.1107/S1600536808003802

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o726

doi:10.1107/S1600536808003802

Open

access

2-Benzyliminomethyl-4-chlorophenol

Xinli Zhang ^a and Zongxiao Li ^a ^*

^aDepartment of Chemistry, Baoji University of Arts and Sciences, Baoji, Shaanxi 721007, People's Republic of China
^*Correspondence e-mail: zhangxinli6008@163.com

(Received 17 December 2007; accepted 4 February 2008; online 20 March 2008)

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 ); Cukurovali et al. (2002 ); Tarafder et al. (2002 ).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.70
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.116
S = 0.98
2177 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.87	2.597 (4)	148

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

Supporting information

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

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

checkCIF report

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.

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

	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.

2-Benzyliminomethyl-4-chlorophenol top

Crystal data top

C₁₄H₁₂ClNO	F(000) = 512
M_r = 245.70	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.3693 (18) Å	Cell parameters from 877 reflections
b = 6.0401 (8) Å	θ = 2.8–25.1°
c = 14.777 (2) Å	µ = 0.29 mm⁻¹
β = 103.911 (2)°	T = 298 K
V = 1244.9 (3) Å³	Rod, yellow
Z = 4	0.52 × 0.38 × 0.11 mm

Data collection top

Bruker SMART APEX diffractometer	2177 independent reflections
Radiation source: fine-focus sealed tube	864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.864, T_max = 0.969	k = −7→6
5203 measured reflections	l = −17→10

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0248P)² + 0.4795P] where P = (F_o² + 2F_c²)/3
2177 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO	V = 1244.9 (3) Å³
M_r = 245.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.3693 (18) Å	µ = 0.29 mm⁻¹
b = 6.0401 (8) Å	T = 298 K
c = 14.777 (2) Å	0.52 × 0.38 × 0.11 mm
β = 103.911 (2)°

Data collection top

Bruker SMART APEX diffractometer	2177 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	864 reflections with I > 2σ(I)
T_min = 0.864, T_max = 0.969	R_int = 0.046
5203 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 0.98	Δρ_max = 0.15 e Å⁻³
2177 reflections	Δρ_min = −0.22 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.24166 (8)	0.1883 (2)	0.07747 (9)	0.1401 (6)
N1	0.6895 (2)	0.0444 (5)	0.2091 (2)	0.0878 (10)
O1	0.60143 (16)	−0.2928 (4)	0.11796 (16)	0.0884 (8)
H1	0.6468	−0.2203	0.1478	0.133*
C1	0.6093 (3)	0.1388 (6)	0.1982 (2)	0.0772 (11)
H1A	0.6070	0.2803	0.2223	0.093*
C2	0.5198 (2)	0.0337 (6)	0.1488 (2)	0.0580 (8)
C3	0.5196 (3)	−0.1769 (6)	0.1098 (2)	0.0613 (9)
C4	0.4338 (3)	−0.2717 (6)	0.0612 (2)	0.0738 (10)
H4	0.4337	−0.4118	0.0350	0.089*
C5	0.3499 (3)	−0.1585 (7)	0.0520 (2)	0.0769 (11)
H5	0.2927	−0.2222	0.0194	0.092*
C6	0.3489 (3)	0.0483 (7)	0.0904 (2)	0.0740 (10)
C7	0.4331 (3)	0.1431 (6)	0.1383 (2)	0.0717 (10)
H7	0.4320	0.2831	0.1642	0.086*
C8	0.7753 (3)	0.1670 (8)	0.2583 (3)	0.1196 (16)
H8A	0.8064	0.0884	0.3147	0.143*
H8B	0.7567	0.3121	0.2759	0.143*
C9	0.8432 (2)	0.1917 (8)	0.1974 (3)	0.0717 (10)
C10	0.8429 (3)	0.3790 (7)	0.1443 (3)	0.0875 (12)
H10	0.8002	0.4932	0.1469	0.105*
C11	0.9053 (3)	0.3980 (8)	0.0877 (3)	0.1031 (15)
H11	0.9042	0.5248	0.0517	0.124*
C12	0.9683 (3)	0.2347 (11)	0.0834 (3)	0.1099 (16)
H12	1.0110	0.2503	0.0454	0.132*
C13	0.9693 (3)	0.0497 (9)	0.1342 (4)	0.1057 (15)
H13	1.0120	−0.0640	0.1308	0.127*
C14	0.9075 (3)	0.0294 (7)	0.1905 (3)	0.0904 (12)
H14	0.9091	−0.0991	0.2255	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1065 (8)	0.1452 (11)	0.1546 (11)	0.0485 (8)	0.0038 (7)	0.0075 (9)
N1	0.0742 (19)	0.117 (3)	0.075 (2)	−0.030 (2)	0.0236 (18)	−0.004 (2)
O1	0.0883 (17)	0.0730 (17)	0.113 (2)	0.0039 (14)	0.0419 (15)	−0.0134 (15)
C1	0.102 (3)	0.080 (3)	0.056 (2)	−0.032 (3)	0.030 (2)	−0.014 (2)
C2	0.078 (2)	0.051 (2)	0.050 (2)	−0.007 (2)	0.0238 (18)	0.0015 (18)
C3	0.078 (2)	0.052 (2)	0.062 (2)	−0.002 (2)	0.033 (2)	0.0004 (19)
C4	0.096 (3)	0.057 (2)	0.078 (3)	−0.015 (2)	0.038 (2)	−0.015 (2)
C5	0.084 (3)	0.091 (3)	0.055 (2)	−0.016 (2)	0.016 (2)	−0.007 (2)
C6	0.082 (3)	0.077 (3)	0.063 (3)	0.014 (2)	0.017 (2)	0.011 (2)
C7	0.102 (3)	0.053 (2)	0.061 (2)	0.001 (2)	0.023 (2)	−0.0014 (19)
C8	0.092 (3)	0.186 (5)	0.086 (3)	−0.059 (3)	0.031 (3)	−0.032 (3)
C9	0.065 (2)	0.079 (3)	0.068 (3)	−0.016 (2)	0.011 (2)	−0.012 (2)
C10	0.072 (3)	0.073 (3)	0.111 (4)	0.005 (2)	0.011 (2)	−0.004 (3)
C11	0.094 (3)	0.099 (4)	0.111 (4)	−0.022 (3)	0.015 (3)	0.030 (3)
C12	0.079 (3)	0.160 (5)	0.096 (4)	−0.018 (3)	0.029 (3)	−0.002 (4)
C13	0.096 (3)	0.111 (4)	0.105 (4)	0.024 (3)	0.013 (3)	−0.021 (3)
C14	0.114 (3)	0.074 (3)	0.075 (3)	−0.004 (3)	0.007 (3)	0.003 (2)

Geometric parameters (Å, º) top

Cl1—C6	1.727 (3)	C7—H7	0.9300
N1—C1	1.260 (4)	C8—C9	1.485 (4)
N1—C8	1.471 (4)	C8—H8A	0.9700
O1—C3	1.349 (3)	C8—H8B	0.9700
O1—H1	0.8200	C9—C14	1.368 (5)
C1—C2	1.462 (4)	C9—C10	1.376 (5)
C1—H1A	0.9300	C10—C11	1.370 (5)
C2—C7	1.385 (4)	C10—H10	0.9300
C2—C3	1.396 (4)	C11—C12	1.351 (5)
C3—C4	1.392 (4)	C11—H11	0.9300
C4—C5	1.365 (4)	C12—C13	1.344 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.373 (4)	C13—C14	1.361 (5)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.372 (4)	C14—H14	0.9300

C1—N1—C8	117.9 (4)	N1—C8—H8A	109.6
C3—O1—H1	109.5	C9—C8—H8A	109.6
N1—C1—C2	122.4 (4)	N1—C8—H8B	109.6
N1—C1—H1A	118.8	C9—C8—H8B	109.6
C2—C1—H1A	118.8	H8A—C8—H8B	108.1
C7—C2—C3	118.4 (3)	C14—C9—C10	117.2 (4)
C7—C2—C1	120.6 (3)	C14—C9—C8	121.8 (5)
C3—C2—C1	121.0 (3)	C10—C9—C8	121.0 (4)
O1—C3—C4	118.5 (3)	C11—C10—C9	120.3 (4)
O1—C3—C2	121.4 (3)	C11—C10—H10	119.9
C4—C3—C2	120.1 (3)	C9—C10—H10	119.9
C5—C4—C3	119.8 (3)	C12—C11—C10	120.8 (4)
C5—C4—H4	120.1	C12—C11—H11	119.6
C3—C4—H4	120.1	C10—C11—H11	119.6
C4—C5—C6	120.8 (3)	C13—C12—C11	119.9 (5)
C4—C5—H5	119.6	C13—C12—H12	120.1
C6—C5—H5	119.6	C11—C12—H12	120.1
C7—C6—C5	119.8 (3)	C12—C13—C14	119.7 (5)
C7—C6—Cl1	120.4 (3)	C12—C13—H13	120.2
C5—C6—Cl1	119.9 (3)	C14—C13—H13	120.2
C6—C7—C2	121.1 (3)	C13—C14—C9	122.2 (4)
C6—C7—H7	119.4	C13—C14—H14	118.9
C2—C7—H7	119.4	C9—C14—H14	118.9
N1—C8—C9	110.2 (3)

C8—N1—C1—C2	178.8 (3)	C3—C2—C7—C6	−0.4 (5)
N1—C1—C2—C7	180.0 (3)	C1—C2—C7—C6	178.5 (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—O1	1.5 (5)	N1—C8—C9—C10	94.8 (4)
C7—C2—C3—C4	0.4 (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—C5	179.8 (3)	C9—C10—C11—C12	−0.5 (6)
C2—C3—C4—C5	−0.2 (5)	C10—C11—C12—C13	0.9 (7)
C3—C4—C5—C6	−0.1 (5)	C11—C12—C13—C14	−0.9 (7)
C4—C5—C6—C7	0.2 (5)	C12—C13—C14—C9	0.3 (6)
C4—C5—C6—Cl1	179.8 (3)	C10—C9—C14—C13	0.2 (5)
C5—C6—C7—C2	0.1 (5)	C8—C9—C14—C13	179.3 (3)
Cl1—C6—C7—C2	−179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.597 (4)	148

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO
M_r	245.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.3693 (18), 6.0401 (8), 14.777 (2)
β (°)	103.911 (2)
V (Å³)	1244.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.52 × 0.38 × 0.11

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.864, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	5203, 2177, 864
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 0.98
No. of reflections	2177
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.597 (4)	147.6

Acknowledgements

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

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. CSD CrossRef PubMed Google Scholar
Bruker (2000). SMART (Version 5.0) and SAINT (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cukurovali, A., Yilmaz, I., Özmen, H. & Ahmedzade, M. (2002). Transition Met. Chem. 27, 171-176. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarafder, M. T. H., Jin, K. T., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2002). Polyhedron, 21, 2547-2554. Web of Science CSD CrossRef CAS Google Scholar