4-[(3-Chloro-2-methyl-phen-yl)imino-meth-yl]phenol.

In the title compound, C(14)H(12)ClNO, the dihedral angle between the aromatic rings is 39.84 (7)°. In th crystal, mol-ecules are connected by O-H⋯N hydrogen bonds into chains parallel to [001]. In addition, a C-H⋯π contact occurs.

Related literature

For the bioactivity of the title compound, see: Corke et al. (1979 ▶); Gorrad & Manson (1989 ▶). For related structures, see: Jothi et al. (2012 ▶); Yaeghoobi et al. (2009 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.70

Orthorhombic,

a = 7.5271 (9) Å

b = 12.4095 (15) Å

c = 12.5800 (14) Å

V = 1175.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 103 K

0.26 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

6050 measured reflections

2042 independent reflections

1856 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.07

2042 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.46 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043140/kj2211sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043140/kj2211Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043140/kj2211Isup3.cml

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

C14H12ClNO	F(000) = 512
Mr = 245.70	Dx = 1.389 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2042 reflections
a = 7.5271 (9) Å	θ = 2.3–30.6°
b = 12.4095 (15) Å	µ = 0.31 mm−1
c = 12.5800 (14) Å	T = 103 K
V = 1175.1 (2) Å3	Block, brown
Z = 4	0.26 × 0.20 × 0.18 mm

Oxford Diffraction Xcalibur Eos diffractometer	1856 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 30.6°, θmin = 2.3°
Detector resolution: 16.0839 pixels mm-1	h = −10→7
ω scans	k = −17→16
6050 measured reflections	l = −16→17
2042 independent reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0838P)2 + 0.0338P] where P = (Fo2 + 2Fc2)/3
2042 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.20725 (8)	0.07415 (5)	0.21487 (5)	0.0206 (2)
O2	−0.2400 (2)	0.06296 (14)	1.08991 (14)	0.0200 (5)
N3	−0.0186 (3)	0.11403 (16)	0.60025 (16)	0.0151 (5)
C4	0.0219 (3)	0.16256 (18)	0.50001 (19)	0.0142 (6)
C5	0.0934 (3)	0.09792 (18)	0.41844 (19)	0.0144 (6)
C6	0.1173 (3)	0.1473 (2)	0.31955 (19)	0.0147 (6)
C7	0.0749 (3)	0.2551 (2)	0.3006 (2)	0.0182 (7)
C8	0.0060 (3)	0.3171 (2)	0.3831 (2)	0.0192 (7)
C9	−0.0203 (3)	0.27089 (18)	0.4822 (2)	0.0165 (6)
C10	0.0205 (3)	0.16597 (19)	0.68499 (19)	0.0157 (6)
C11	−0.0336 (3)	0.13243 (19)	0.79125 (19)	0.0146 (6)
C12	−0.1136 (3)	0.03193 (19)	0.81002 (19)	0.0162 (6)
C13	−0.1794 (3)	0.00693 (19)	0.91011 (19)	0.0154 (6)
C14	−0.1689 (3)	0.08211 (19)	0.99228 (18)	0.0148 (6)
C15	−0.0820 (3)	0.18052 (19)	0.9758 (2)	0.0170 (6)
C16	−0.0153 (3)	0.20481 (19)	0.8757 (2)	0.0161 (6)
C17	0.1424 (3)	−0.01811 (19)	0.4369 (2)	0.0191 (7)
H2	−0.28810	0.00190	1.09040	0.0300*
H7	0.09280	0.28580	0.23230	0.0220*
H8	−0.02280	0.39070	0.37150	0.0230*
H9	−0.06730	0.31310	0.53850	0.0200*
H10	0.08860	0.23010	0.67830	0.0190*
H12	−0.12270	−0.01910	0.75400	0.0190*
H13	−0.23160	−0.06160	0.92270	0.0180*
H15	−0.06890	0.23030	1.03260	0.0200*
H16	0.04360	0.27160	0.86450	0.0190*
H17A	0.09600	−0.06240	0.37870	0.0290*
H17B	0.09100	−0.04250	0.50440	0.0290*
H17C	0.27200	−0.02500	0.43980	0.0290*

	U11	U22	U33	U12	U13	U23
Cl1	0.0193 (3)	0.0256 (3)	0.0169 (3)	−0.0005 (2)	0.0037 (2)	−0.0025 (2)
O2	0.0225 (9)	0.0216 (8)	0.0160 (8)	−0.0038 (7)	0.0057 (7)	−0.0002 (7)
N3	0.0108 (9)	0.0184 (9)	0.0160 (9)	−0.0002 (7)	0.0016 (8)	0.0019 (7)
C4	0.0096 (10)	0.0162 (10)	0.0168 (11)	−0.0014 (8)	0.0009 (9)	0.0013 (8)
C5	0.0083 (9)	0.0180 (10)	0.0170 (11)	−0.0006 (8)	−0.0017 (9)	0.0008 (8)
C6	0.0082 (9)	0.0213 (10)	0.0146 (10)	−0.0013 (8)	0.0015 (8)	−0.0017 (8)
C7	0.0150 (11)	0.0215 (11)	0.0180 (12)	−0.0024 (9)	0.0001 (9)	0.0043 (9)
C8	0.0147 (11)	0.0183 (11)	0.0246 (12)	−0.0002 (9)	−0.0011 (10)	0.0039 (9)
C9	0.0108 (10)	0.0173 (11)	0.0214 (12)	0.0014 (8)	0.0012 (9)	−0.0009 (9)
C10	0.0108 (10)	0.0171 (10)	0.0191 (11)	0.0005 (8)	0.0020 (9)	0.0000 (8)
C11	0.0104 (9)	0.0191 (10)	0.0144 (10)	0.0004 (8)	0.0002 (9)	0.0009 (9)
C12	0.0133 (10)	0.0189 (10)	0.0164 (11)	0.0002 (8)	−0.0002 (9)	−0.0003 (8)
C13	0.0121 (10)	0.0175 (10)	0.0167 (10)	−0.0003 (8)	0.0017 (9)	0.0002 (9)
C14	0.0121 (9)	0.0175 (10)	0.0148 (10)	0.0013 (8)	0.0016 (8)	0.0001 (8)
C15	0.0172 (11)	0.0178 (10)	0.0160 (11)	−0.0013 (9)	−0.0001 (10)	−0.0026 (8)
C16	0.0135 (11)	0.0151 (10)	0.0196 (11)	−0.0014 (8)	−0.0012 (9)	0.0008 (9)
C17	0.0185 (12)	0.0180 (11)	0.0207 (12)	0.0029 (9)	0.0033 (10)	0.0003 (9)

Cl1—C6	1.737 (2)	C12—C13	1.388 (3)
O2—C14	1.361 (3)	C13—C14	1.395 (3)
O2—H2	0.8400	C14—C15	1.401 (3)
N3—C4	1.430 (3)	C15—C16	1.389 (4)
N3—C10	1.280 (3)	C7—H7	0.9500
C4—C9	1.399 (3)	C8—H8	0.9500
C4—C5	1.409 (3)	C9—H9	0.9500
C5—C6	1.398 (3)	C10—H10	0.9500
C5—C17	1.504 (3)	C12—H12	0.9500
C6—C7	1.396 (3)	C13—H13	0.9500
C7—C8	1.392 (3)	C15—H15	0.9500
C8—C9	1.386 (4)	C16—H16	0.9500
C10—C11	1.458 (3)	C17—H17A	0.9800
C11—C16	1.398 (3)	C17—H17B	0.9800
C11—C12	1.405 (3)	C17—H17C	0.9800
C14—O2—H2	109.00	C11—C16—C15	120.9 (2)
C4—N3—C10	118.2 (2)	C6—C7—H7	120.00
N3—C4—C5	118.9 (2)	C8—C7—H7	120.00
C5—C4—C9	121.1 (2)	C7—C8—H8	120.00
N3—C4—C9	119.8 (2)	C9—C8—H8	120.00
C4—C5—C6	116.6 (2)	C4—C9—H9	120.00
C4—C5—C17	121.7 (2)	C8—C9—H9	120.00
C6—C5—C17	121.7 (2)	N3—C10—H10	118.00
Cl1—C6—C5	119.71 (18)	C11—C10—H10	118.00
Cl1—C6—C7	117.42 (18)	C11—C12—H12	120.00
C5—C6—C7	122.9 (2)	C13—C12—H12	120.00
C6—C7—C8	119.2 (2)	C12—C13—H13	120.00
C7—C8—C9	119.7 (2)	C14—C13—H13	120.00
C4—C9—C8	120.6 (2)	C14—C15—H15	120.00
N3—C10—C11	123.8 (2)	C16—C15—H15	120.00
C10—C11—C16	119.1 (2)	C11—C16—H16	120.00
C12—C11—C16	119.0 (2)	C15—C16—H16	119.00
C10—C11—C12	121.8 (2)	C5—C17—H17A	110.00
C11—C12—C13	120.3 (2)	C5—C17—H17B	109.00
C12—C13—C14	120.2 (2)	C5—C17—H17C	109.00
O2—C14—C13	122.0 (2)	H17A—C17—H17B	109.00
O2—C14—C15	118.0 (2)	H17A—C17—H17C	109.00
C13—C14—C15	120.0 (2)	H17B—C17—H17C	109.00
C14—C15—C16	119.5 (2)
C10—N3—C4—C5	138.4 (2)	C6—C7—C8—C9	−0.4 (3)
C10—N3—C4—C9	−45.7 (3)	C7—C8—C9—C4	0.0 (3)
C4—N3—C10—C11	171.9 (2)	N3—C10—C11—C12	8.7 (4)
N3—C4—C5—C6	175.1 (2)	N3—C10—C11—C16	−167.4 (2)
N3—C4—C5—C17	−5.2 (3)	C10—C11—C12—C13	−173.6 (2)
C9—C4—C5—C6	−0.8 (3)	C16—C11—C12—C13	2.5 (3)
C9—C4—C5—C17	178.9 (2)	C10—C11—C16—C15	173.2 (2)
N3—C4—C9—C8	−175.3 (2)	C12—C11—C16—C15	−2.9 (3)
C5—C4—C9—C8	0.6 (3)	C11—C12—C13—C14	1.0 (3)
C4—C5—C6—Cl1	179.21 (17)	C12—C13—C14—O2	176.5 (2)
C4—C5—C6—C7	0.5 (3)	C12—C13—C14—C15	−4.0 (3)
C17—C5—C6—Cl1	−0.5 (3)	O2—C14—C15—C16	−177.0 (2)
C17—C5—C6—C7	−179.2 (2)	C13—C14—C15—C16	3.5 (3)
Cl1—C6—C7—C8	−178.66 (18)	C14—C15—C16—C11	0.0 (3)
C5—C6—C7—C8	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3i	0.84	2.05	2.854 (3)	160
C12—H12···O2ii	0.95	2.37	3.204 (3)	146
C17—H17B···N3	0.98	2.43	2.895 (3)	108
C17—H17C···Cgiii	0.98	2.73	3.649 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N3i	0.84	2.05	2.854 (3)	160
C17—H17C⋯Cg ii	0.98	2.73	3.649 (2)	157

Symmetry codes: (i) ; (ii) .