2-[(E)-(2-Chloro-phen-yl)imino-meth-yl]-6-methyl-phenol.

The title compound, C(14)H(12)ClNO, a Schiff base derived from 3-methyl-salicyl-aldehyde, crystallizes in the phenol-imine tautomeric form with an E conformation for the imine functionality. The mol-ecule is not planar, the dihedral angle between the aromatic rings being 36.38 (5)°. The hy-droxy H atom is involved in a strong intra-molecular O-H⋯N hydrogen bond, generating an S(6) ring.

Related literature

For background information and applications of Schiff base complexes, see: Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶); Cohen et al. (1964 ▶); Henrici-Olive & Olive (1984 ▶); Garnovskii et al. (1993 ▶). For related structures, see: Köysal et al. (2007 ▶); Kılıç et al. (2009 ▶); Şahin et al. (2009 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.70

Orthorhombic,

a = 7.8318 (14) Å

b = 11.693 (2) Å

c = 13.250 (2) Å

V = 1213.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.21 × 0.11 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.940, T max = 0.982

6803 measured reflections

2477 independent reflections

1486 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.096

S = 1.00

2477 reflections

158 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 1034 Friedel pairs

Flack parameter: −0.06 (9)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033969/zq2056sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033969/zq2056Isup2.hkl

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

C14H12ClNO	F(000) = 512
Mr = 245.70	Dx = 1.345 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1163 reflections
a = 7.8318 (14) Å	θ = 3.1–28.8°
b = 11.693 (2) Å	µ = 0.30 mm−1
c = 13.250 (2) Å	T = 293 K
V = 1213.4 (4) Å3	Needle, yellow
Z = 4	0.21 × 0.11 × 0.06 mm

Bruker APEXII CCD area-detector diffractometer	2477 independent reflections
Radiation source: fine-focus sealed tube	1486 reflections with I > 2σ(I)
graphite	Rint = 0.070
φ and ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.940, Tmax = 0.982	k = −14→14
6803 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0358P)2 + 0.0414P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2477 reflections	Δρmax = 0.15 e Å−3
158 parameters	Δρmin = −0.14 e Å−3
1 restraint	Absolute structure: Flack (1983), 1034 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (9)

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.

	x	y	z	Uiso*/Ueq
Cl1	−0.30427 (11)	−0.84282 (9)	−0.18201 (8)	0.0873 (3)
C11	−0.2023 (4)	−0.5269 (3)	−0.6436 (3)	0.0609 (9)
H11	−0.1358	−0.4949	−0.6945	0.073*
C2	−0.6147 (5)	−0.8244 (3)	−0.0959 (3)	0.0673 (9)
H2	−0.5727	−0.8740	−0.0469	0.081*
C4	−0.8405 (4)	−0.7124 (3)	−0.1622 (3)	0.0704 (10)
H4	−0.9518	−0.6851	−0.1577	0.085*
C13	−0.2304 (4)	−0.5959 (2)	−0.4763 (2)	0.0460 (7)
N1	−0.4592 (3)	−0.68266 (18)	−0.32559 (19)	0.0510 (6)
C8	−0.4038 (3)	−0.6210 (2)	−0.4942 (2)	0.0446 (7)
C5	−0.7384 (3)	−0.6793 (3)	−0.2418 (3)	0.0600 (8)
H5	−0.7817	−0.6305	−0.2910	0.072*
C1	−0.5125 (4)	−0.7905 (2)	−0.1741 (2)	0.0546 (8)
C3	−0.7793 (5)	−0.7849 (3)	−0.0899 (3)	0.0726 (10)
H3	−0.8492	−0.8075	−0.0368	0.087*
C9	−0.4702 (4)	−0.5986 (2)	−0.5894 (2)	0.0568 (8)
H9	−0.5835	−0.6167	−0.6030	0.068*
C7	−0.5128 (3)	−0.6658 (2)	−0.4159 (2)	0.0476 (7)
H7	−0.6257	−0.6830	−0.4313	0.057*
C12	−0.1285 (3)	−0.5488 (2)	−0.5514 (2)	0.0509 (8)
C6	−0.5706 (3)	−0.7186 (2)	−0.2491 (2)	0.0495 (7)
C10	−0.3721 (4)	−0.5507 (3)	−0.6631 (2)	0.0638 (9)
H10	−0.4190	−0.5342	−0.7260	0.077*
C14	0.0568 (4)	−0.5250 (3)	−0.5305 (3)	0.0781 (11)
H14C	0.1143	−0.5953	−0.5150	0.117*
H14A	0.0662	−0.4737	−0.4742	0.117*
H14B	0.1081	−0.4907	−0.5889	0.117*
O1	−0.1569 (2)	−0.61668 (18)	−0.38591 (17)	0.0618 (6)
H1	−0.233 (3)	−0.648 (3)	−0.3472 (19)	0.074*

	U11	U22	U33	U12	U13	U23
Cl1	0.0762 (5)	0.1058 (7)	0.0799 (7)	0.0203 (5)	−0.0073 (5)	0.0146 (6)
C11	0.072 (2)	0.0524 (19)	0.058 (2)	0.0033 (17)	0.0238 (19)	0.0008 (17)
C2	0.089 (3)	0.054 (2)	0.059 (2)	−0.0124 (19)	−0.002 (2)	0.0131 (19)
C4	0.064 (2)	0.065 (2)	0.083 (3)	−0.0066 (17)	0.016 (2)	0.000 (2)
C13	0.0515 (19)	0.0393 (16)	0.0471 (19)	0.0069 (13)	0.0008 (15)	−0.0042 (15)
N1	0.0543 (13)	0.0510 (14)	0.0477 (16)	−0.0051 (11)	0.0029 (14)	0.0016 (14)
C8	0.0473 (18)	0.0412 (17)	0.0452 (19)	0.0026 (12)	0.0044 (15)	−0.0075 (15)
C5	0.0581 (18)	0.0538 (19)	0.068 (2)	−0.0021 (15)	0.0058 (17)	0.0120 (18)
C1	0.0629 (18)	0.0511 (16)	0.0499 (19)	−0.0042 (15)	−0.0015 (18)	−0.0013 (18)
C3	0.087 (3)	0.064 (2)	0.067 (2)	−0.0186 (19)	0.022 (2)	0.002 (2)
C9	0.0564 (17)	0.0652 (18)	0.049 (2)	0.0009 (15)	−0.0027 (17)	−0.0051 (19)
C7	0.0468 (15)	0.0460 (16)	0.050 (2)	−0.0023 (14)	−0.0025 (16)	−0.0025 (17)
C12	0.0527 (17)	0.0432 (16)	0.057 (2)	0.0023 (14)	0.0098 (18)	−0.0034 (16)
C6	0.0539 (18)	0.0423 (16)	0.0523 (19)	−0.0094 (13)	0.0014 (16)	−0.0013 (17)
C10	0.079 (2)	0.071 (2)	0.042 (2)	0.0057 (18)	0.0028 (18)	−0.0004 (19)
C14	0.057 (2)	0.085 (2)	0.093 (3)	−0.0041 (17)	0.0114 (19)	0.004 (2)
O1	0.0516 (12)	0.0784 (16)	0.0554 (15)	−0.0011 (11)	−0.0025 (11)	0.0044 (12)

Cl1—C1	1.745 (3)	C8—C9	1.388 (4)
C11—C12	1.376 (4)	C8—C7	1.442 (4)
C11—C10	1.384 (4)	C5—C6	1.396 (4)
C11—H11	0.9300	C5—H5	0.9300
C2—C1	1.369 (4)	C1—C6	1.378 (4)
C2—C3	1.372 (4)	C3—H3	0.9300
C2—H2	0.9300	C9—C10	1.363 (4)
C4—C3	1.366 (4)	C9—H9	0.9300
C4—C5	1.379 (4)	C7—H7	0.9300
C4—H4	0.9300	C12—C14	1.503 (4)
C13—O1	1.351 (3)	C10—H10	0.9300
C13—C12	1.389 (4)	C14—H14C	0.9600
C13—C8	1.410 (4)	C14—H14A	0.9600
N1—C7	1.283 (3)	C14—H14B	0.9600
N1—C6	1.402 (3)	O1—H1	0.87 (3)
C12—C11—C10	122.2 (3)	C2—C3—H3	120.1
C12—C11—H11	118.9	C10—C9—C8	121.2 (3)
C10—C11—H11	118.9	C10—C9—H9	119.4
C1—C2—C3	119.7 (3)	C8—C9—H9	119.4
C1—C2—H2	120.1	N1—C7—C8	122.2 (3)
C3—C2—H2	120.1	N1—C7—H7	118.9
C3—C4—C5	120.5 (3)	C8—C7—H7	118.9
C3—C4—H4	119.8	C11—C12—C13	117.9 (3)
C5—C4—H4	119.8	C11—C12—C14	122.3 (3)
O1—C13—C12	117.5 (3)	C13—C12—C14	119.8 (3)
O1—C13—C8	121.4 (3)	C1—C6—C5	117.5 (3)
C12—C13—C8	121.1 (3)	C1—C6—N1	119.9 (3)
C7—N1—C6	121.1 (2)	C5—C6—N1	122.5 (3)
C9—C8—C13	118.3 (3)	C9—C10—C11	119.3 (3)
C9—C8—C7	120.0 (3)	C9—C10—H10	120.3
C13—C8—C7	121.7 (3)	C11—C10—H10	120.3
C4—C5—C6	120.4 (3)	C12—C14—H14C	109.5
C4—C5—H5	119.8	C12—C14—H14A	109.5
C6—C5—H5	119.8	H14C—C14—H14A	109.5
C2—C1—C6	122.0 (3)	C12—C14—H14B	109.5
C2—C1—Cl1	119.4 (3)	H14C—C14—H14B	109.5
C6—C1—Cl1	118.6 (2)	H14A—C14—H14B	109.5
C4—C3—C2	119.9 (3)	C13—O1—H1	108 (2)
C4—C3—H3	120.1
O1—C13—C8—C9	−179.2 (2)	C10—C11—C12—C14	178.9 (3)
C12—C13—C8—C9	0.7 (4)	O1—C13—C12—C11	−179.7 (2)
O1—C13—C8—C7	2.5 (4)	C8—C13—C12—C11	0.4 (4)
C12—C13—C8—C7	−177.6 (2)	O1—C13—C12—C14	1.0 (4)
C3—C4—C5—C6	−0.6 (4)	C8—C13—C12—C14	−178.9 (3)
C3—C2—C1—C6	−1.1 (5)	C2—C1—C6—C5	1.1 (4)
C3—C2—C1—Cl1	−179.1 (3)	Cl1—C1—C6—C5	179.1 (2)
C5—C4—C3—C2	0.6 (5)	C2—C1—C6—N1	177.5 (3)
C1—C2—C3—C4	0.2 (5)	Cl1—C1—C6—N1	−4.5 (3)
C13—C8—C9—C10	−1.8 (4)	C4—C5—C6—C1	−0.2 (4)
C7—C8—C9—C10	176.5 (3)	C4—C5—C6—N1	−176.6 (3)
C6—N1—C7—C8	175.4 (2)	C7—N1—C6—C1	146.1 (3)
C9—C8—C7—N1	−176.7 (3)	C7—N1—C6—C5	−37.6 (4)
C13—C8—C7—N1	1.6 (4)	C8—C9—C10—C11	1.8 (5)
C10—C11—C12—C13	−0.4 (4)	C12—C11—C10—C9	−0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.87 (1)	1.84 (2)	2.615 (3)	148 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.87 (1)	1.84 (2)	2.615 (3)	148 (3)