2-[(4-Chlorobenzyl)iminomethyl]phenol.

The title Schiff base compound, C(14)H(12)ClNO, was prepared from 4-chloro-benzyl-amine and salicyl-aldehyde. The mol-ecule is V-shaped: the dihedral angle between the aromatic rings is 67.51 (5)°. The rings are located on the opposite side of the C=N bond, giving an E configuration. An intra-molecular N-H⋯O hydrogen bond generates a S(6) ring. In the crystal structure, only weak non-classical C-H⋯O contacts are observed.

Related literature

For background to Schiff base ligands and their biological activity, see: Adsule et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For related structures, see: Tariq et al. (2010 ▶); Khalaji & Simpson (2009 ▶). For the graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ▶). For the synthesis, see: Kannappan et al. (2005 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.7

Orthorhombic,

a = 6.2876 (2) Å

b = 12.2267 (3) Å

c = 16.2664 (5) Å

V = 1250.51 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.45 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker,2008 ▶) T min = 0.933, T max = 0.944

10586 measured reflections

1479 independent reflections

1119 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.04

1479 reflections

155 parameters

143 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031508/ds2046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031508/ds2046Isup2.hkl

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

C14H12ClNO	F(000) = 512
Mr = 245.7	Dx = 1.305 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5069 reflections
a = 6.2876 (2) Å	θ = 2.5–22.8°
b = 12.2267 (3) Å	µ = 0.29 mm−1
c = 16.2664 (5) Å	T = 296 K
V = 1250.51 (6) Å3	Prism, yellow
Z = 4	0.45 × 0.20 × 0.20 mm

Bruker SMART APEXII CCD area-detector diffractometer	1479 independent reflections
Radiation source: Mo Kα	1119 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 26.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker,2008)	h = −7→7
Tmin = 0.933, Tmax = 0.944	k = −15→15
10586 measured reflections	l = −17→20

Refinement on F2	143 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0436P)2 + 0.2636P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.20 e Å−3
1479 reflections	Δρmin = −0.29 e Å−3
155 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.7530 (5)	−0.3508 (3)	0.9530 (2)	0.0818 (9)
H1	0.8887	−0.3216	0.9586	0.098*
C2	0.7031 (8)	−0.4471 (3)	0.9927 (2)	0.1008 (12)
H2	0.8045	−0.4827	1.0246	0.121*
C3	0.5038 (8)	−0.4895 (3)	0.9849 (2)	0.0974 (10)
H3	0.4697	−0.5542	1.0119	0.117*
C4	0.3524 (6)	−0.4384 (2)	0.93779 (19)	0.0815 (8)
H4	0.2173	−0.4687	0.9329	0.098*
C5	0.6053 (4)	−0.2970 (2)	0.90492 (15)	0.0587 (6)
C6	0.4010 (4)	−0.3415 (2)	0.89741 (17)	0.0616 (7)
C7	0.6613 (5)	−0.1965 (2)	0.86325 (17)	0.0711 (7)
H7	0.7986	−0.1693	0.869	0.085*
C8	0.5987 (7)	−0.0429 (3)	0.7791 (3)	0.1127 (13)
H8A	0.5962	−0.0524	0.7199	0.135*
H8B	0.7433	−0.0256	0.7954	0.135*
C9	0.4535 (6)	0.0487 (2)	0.80299 (19)	0.0789 (9)
C10	0.2539 (7)	0.0585 (3)	0.76832 (19)	0.0857 (9)
H10	0.2115	0.0083	0.7287	0.103*
C11	0.1157 (5)	0.1408 (2)	0.79093 (19)	0.0802 (8)
H11	−0.0181	0.1461	0.7669	0.096*
C12	0.1783 (5)	0.2140 (2)	0.84889 (19)	0.0748 (8)
C13	0.3760 (5)	0.2080 (3)	0.8837 (2)	0.0845 (9)
H13	0.4181	0.259	0.9228	0.101*
C14	0.5117 (5)	0.1255 (3)	0.8600 (2)	0.0877 (9)
H14	0.6466	0.1219	0.8833	0.105*
Cl1	0.00322 (17)	0.31716 (7)	0.87960 (8)	0.1204 (4)
N1	0.5305 (4)	−0.14462 (19)	0.81941 (15)	0.0780 (7)
O1	0.2507 (3)	−0.29358 (18)	0.85185 (14)	0.0864 (6)
H1A	0.2973	−0.2364	0.8325	0.13*

	U11	U22	U33	U12	U13	U23
C1	0.0706 (17)	0.0856 (19)	0.089 (2)	0.0140 (17)	−0.0191 (17)	−0.0254 (16)
C2	0.122 (3)	0.093 (2)	0.087 (2)	0.033 (2)	−0.020 (2)	−0.001 (2)
C3	0.137 (3)	0.0691 (18)	0.086 (2)	0.012 (2)	0.014 (3)	0.0082 (16)
C4	0.086 (2)	0.0660 (16)	0.092 (2)	−0.0105 (17)	0.0111 (18)	−0.0036 (16)
C5	0.0583 (13)	0.0605 (13)	0.0573 (14)	0.0023 (12)	0.0008 (12)	−0.0156 (12)
C6	0.0605 (14)	0.0610 (14)	0.0632 (15)	−0.0004 (12)	−0.0037 (13)	−0.0079 (12)
C7	0.0608 (14)	0.0639 (15)	0.0888 (19)	−0.0073 (14)	0.0169 (16)	−0.0173 (14)
C8	0.129 (3)	0.0797 (19)	0.130 (3)	0.006 (2)	0.059 (3)	0.028 (2)
C9	0.091 (2)	0.0639 (16)	0.0820 (19)	−0.0101 (16)	0.0210 (18)	0.0202 (14)
C10	0.111 (2)	0.0767 (19)	0.0700 (18)	−0.0259 (19)	0.0009 (19)	0.0051 (16)
C11	0.0789 (18)	0.0806 (18)	0.0811 (19)	−0.0202 (17)	−0.0148 (17)	0.0214 (16)
C12	0.0780 (17)	0.0599 (14)	0.0864 (19)	−0.0126 (15)	0.0028 (16)	0.0179 (14)
C13	0.090 (2)	0.0751 (17)	0.089 (2)	−0.0144 (17)	−0.0140 (19)	−0.0004 (16)
C14	0.0728 (18)	0.088 (2)	0.102 (2)	−0.0088 (19)	−0.007 (2)	0.0208 (18)
Cl1	0.1050 (7)	0.0765 (5)	0.1799 (10)	0.0032 (6)	0.0167 (8)	0.0086 (6)
N1	0.0850 (16)	0.0658 (13)	0.0831 (15)	−0.0002 (14)	0.0188 (15)	0.0061 (12)
O1	0.0654 (11)	0.0876 (15)	0.1063 (16)	−0.0097 (12)	−0.0213 (12)	0.0083 (13)

C1—C2	1.379 (5)	C8—C9	1.497 (5)
C1—C5	1.380 (4)	C8—H8A	0.97
C1—H1	0.93	C8—H8B	0.97
C2—C3	1.362 (6)	C9—C14	1.369 (4)
C2—H2	0.93	C9—C10	1.381 (5)
C3—C4	1.372 (5)	C10—C11	1.379 (5)
C3—H3	0.93	C10—H10	0.93
C4—C6	1.389 (4)	C11—C12	1.358 (4)
C4—H4	0.93	C11—H11	0.93
C5—C6	1.401 (4)	C12—C13	1.367 (4)
C5—C7	1.446 (4)	C12—Cl1	1.747 (3)
C6—O1	1.336 (3)	C13—C14	1.376 (5)
C7—N1	1.260 (3)	C13—H13	0.93
C7—H7	0.93	C14—H14	0.93
C8—N1	1.470 (4)	O1—H1A	0.82
C2—C1—C5	121.3 (3)	N1—C8—H8B	109.7
C2—C1—H1	119.3	C9—C8—H8B	109.7
C5—C1—H1	119.3	H8A—C8—H8B	108.2
C3—C2—C1	119.3 (3)	C14—C9—C10	117.4 (3)
C3—C2—H2	120.3	C14—C9—C8	121.8 (3)
C1—C2—H2	120.3	C10—C9—C8	120.9 (4)
C2—C3—C4	121.1 (3)	C11—C10—C9	121.8 (3)
C2—C3—H3	119.4	C11—C10—H10	119.1
C4—C3—H3	119.4	C9—C10—H10	119.1
C3—C4—C6	120.0 (3)	C12—C11—C10	118.9 (3)
C3—C4—H4	120	C12—C11—H11	120.5
C6—C4—H4	120	C10—C11—H11	120.5
C1—C5—C6	118.7 (3)	C11—C12—C13	121.0 (3)
C1—C5—C7	120.5 (3)	C11—C12—Cl1	119.4 (3)
C6—C5—C7	120.8 (3)	C13—C12—Cl1	119.5 (3)
O1—C6—C4	118.7 (3)	C12—C13—C14	119.1 (3)
O1—C6—C5	121.8 (2)	C12—C13—H13	120.4
C4—C6—C5	119.5 (3)	C14—C13—H13	120.4
N1—C7—C5	122.3 (3)	C9—C14—C13	121.8 (3)
N1—C7—H7	118.9	C9—C14—H14	119.1
C5—C7—H7	118.9	C13—C14—H14	119.1
N1—C8—C9	109.8 (3)	C7—N1—C8	119.2 (3)
N1—C8—H8A	109.7	C6—O1—H1A	109.5
C9—C8—H8A	109.7
C5—C1—C2—C3	−0.4 (5)	N1—C8—C9—C10	−76.8 (4)
C1—C2—C3—C4	0.3 (5)	C14—C9—C10—C11	−1.2 (4)
C2—C3—C4—C6	−0.3 (5)	C8—C9—C10—C11	178.4 (3)
C2—C1—C5—C6	0.5 (4)	C9—C10—C11—C12	0.0 (4)
C2—C1—C5—C7	−179.5 (3)	C10—C11—C12—C13	1.1 (4)
C3—C4—C6—O1	179.9 (3)	C10—C11—C12—Cl1	−178.8 (2)
C3—C4—C6—C5	0.3 (4)	C11—C12—C13—C14	−0.8 (4)
C1—C5—C6—O1	−179.9 (2)	Cl1—C12—C13—C14	179.1 (2)
C7—C5—C6—O1	0.1 (4)	C10—C9—C14—C13	1.5 (4)
C1—C5—C6—C4	−0.4 (4)	C8—C9—C14—C13	−178.1 (3)
C7—C5—C6—C4	179.6 (2)	C12—C13—C14—C9	−0.6 (5)
C1—C5—C7—N1	−179.4 (3)	C5—C7—N1—C8	179.8 (3)
C6—C5—C7—N1	0.6 (4)	C9—C8—N1—C7	−124.3 (3)
N1—C8—C9—C14	102.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.86	2.587 (3)	147.
C11—H11···O1i	0.93	2.53	3.369 (4)	150.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.86	2.587 (3)	147
C11—H11⋯O1i	0.93	2.53	3.369 (4)	150

Symmetry code: (i) .