Crystal structure of 4-chloro-2-{(E)-[(3,4-di-methyl-phen-yl)imino]-meth-yl}phenol.

In the title compound, C15H14ClNO, which is isostructural with its bromo analogue [Tahir et al. (2012 ▶). Acta Cryst., E68, o2730], the dihedral angle between the planes of the aromatic rings is 2.71 (7)° and an intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. In the crystal, extremely weak C-H⋯π inter-actions link the mol-ecules into a three-dimensional network.

Related literature

For related structures, see: Demircioğlu et al. (2014 ▸); Jin et al. (2012 ▸); Sun et al. (2013 ▸); Tahir et al. (2012 ▸).

Experimental

Crystal data

C15H14ClNO

M = 259.72

Monoclinic,

a = 12.1875 (10) Å

b = 7.4438 (5) Å

c = 14.3141 (12) Å

β = 101.549 (4)°

V = 1272.30 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.25 × 0.20 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▸) T min = 0.933, T max = 0.968

10293 measured reflections

2785 independent reflections

1871 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.116

S = 1.04

2785 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015009354/hb7424sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009354/hb7424Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009354/hb7424Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009354/hb7424fig1.tif

View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted line shows intra­molecular H-bonding.

Click here for additional data file.

. DOI: 10.1107/S2056989015009354/hb7424fig2.tif

Packing diagram for the title compound.

CCDC reference: 1401503

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H14ClNO	F(000) = 544
Mr = 259.72	Dx = 1.356 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.1875 (10) Å	Cell parameters from 1871 reflections
b = 7.4438 (5) Å	θ = 2.0–27.0°
c = 14.3141 (12) Å	µ = 0.29 mm−1
β = 101.549 (4)°	T = 296 K
V = 1272.30 (17) Å3	Plate, light yellow
Z = 4	0.25 × 0.20 × 0.14 mm

Bruker Kappa APEXII CCD diffractometer	2785 independent reflections
Radiation source: fine-focus sealed tube	1871 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 7.80 pixels mm-1	θmax = 27.0°, θmin = 2.0°
ω scans	h = −15→12
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −8→9
Tmin = 0.933, Tmax = 0.968	l = −18→15
10293 measured 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.2053P] where P = (Fo2 + 2Fc2)/3
2785 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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	0.31558 (4)	0.47763 (8)	0.94032 (3)	0.0702 (2)
O1	0.45252 (11)	0.6419 (2)	0.58212 (9)	0.0684 (4)
H1	0.4036	0.6151	0.5361	0.103*
N1	0.26240 (12)	0.51118 (17)	0.49303 (10)	0.0442 (4)
C1	0.41674 (14)	0.6064 (2)	0.66249 (12)	0.0462 (4)
C2	0.31233 (14)	0.5273 (2)	0.66205 (11)	0.0400 (4)
C3	0.28167 (14)	0.4894 (2)	0.74847 (12)	0.0434 (4)
H3	0.2128	0.4363	0.7492	0.052*
C4	0.35292 (14)	0.5305 (2)	0.83271 (12)	0.0447 (4)
C5	0.45476 (15)	0.6104 (2)	0.83316 (12)	0.0499 (4)
H5	0.5022	0.6383	0.8907	0.060*
C6	0.48620 (15)	0.6486 (2)	0.74880 (13)	0.0524 (5)
H6	0.5549	0.7035	0.7493	0.063*
C7	0.23682 (15)	0.4821 (2)	0.57324 (12)	0.0432 (4)
H7	0.1679	0.4304	0.5753	0.052*
C8	0.18970 (13)	0.4694 (2)	0.40504 (11)	0.0394 (4)
C9	0.23021 (14)	0.5050 (2)	0.32363 (12)	0.0414 (4)
H9	0.3016	0.5534	0.3296	0.050*
C10	0.16807 (14)	0.4712 (2)	0.23319 (12)	0.0407 (4)
C11	0.06064 (14)	0.3993 (2)	0.22426 (12)	0.0429 (4)
C12	0.02122 (14)	0.3625 (2)	0.30650 (12)	0.0455 (4)
H12	−0.0499	0.3133	0.3010	0.055*
C13	0.08330 (14)	0.3962 (2)	0.39585 (12)	0.0456 (4)
H13	0.0544	0.3701	0.4497	0.055*
C14	0.21523 (18)	0.5150 (3)	0.14640 (13)	0.0576 (5)
H14A	0.2165	0.4083	0.1089	0.086*
H14B	0.2901	0.5603	0.1659	0.086*
H14C	0.1693	0.6042	0.1090	0.086*
C15	−0.01190 (16)	0.3653 (3)	0.12815 (13)	0.0599 (5)
H15A	0.0236	0.2788	0.0943	0.090*
H15B	−0.0225	0.4756	0.0927	0.090*
H15C	−0.0832	0.3200	0.1360	0.090*

	U11	U22	U33	U12	U13	U23
Cl1	0.0742 (4)	0.1002 (4)	0.0366 (3)	−0.0049 (3)	0.0120 (2)	0.0047 (2)
O1	0.0658 (9)	0.0930 (10)	0.0483 (8)	−0.0276 (8)	0.0159 (7)	0.0033 (7)
N1	0.0472 (8)	0.0498 (8)	0.0349 (8)	−0.0009 (6)	0.0069 (6)	−0.0023 (6)
C1	0.0493 (10)	0.0475 (10)	0.0428 (10)	−0.0042 (8)	0.0116 (8)	0.0025 (7)
C2	0.0427 (9)	0.0390 (9)	0.0376 (9)	0.0015 (7)	0.0061 (7)	−0.0012 (7)
C3	0.0430 (10)	0.0469 (10)	0.0407 (9)	0.0001 (7)	0.0093 (8)	−0.0005 (7)
C4	0.0493 (11)	0.0476 (10)	0.0364 (9)	0.0048 (8)	0.0065 (8)	0.0002 (7)
C5	0.0519 (11)	0.0500 (10)	0.0432 (10)	−0.0005 (8)	−0.0013 (8)	−0.0027 (8)
C6	0.0476 (11)	0.0523 (11)	0.0550 (12)	−0.0103 (8)	0.0048 (9)	−0.0008 (9)
C7	0.0440 (10)	0.0450 (9)	0.0404 (10)	−0.0016 (7)	0.0080 (8)	−0.0015 (7)
C8	0.0421 (10)	0.0383 (9)	0.0376 (9)	0.0011 (7)	0.0073 (7)	−0.0016 (7)
C9	0.0404 (9)	0.0421 (9)	0.0423 (10)	−0.0036 (7)	0.0102 (7)	−0.0015 (7)
C10	0.0480 (10)	0.0368 (9)	0.0389 (9)	0.0015 (7)	0.0125 (7)	0.0007 (7)
C11	0.0482 (10)	0.0368 (9)	0.0417 (10)	0.0013 (7)	0.0040 (7)	−0.0007 (7)
C12	0.0410 (9)	0.0474 (10)	0.0482 (10)	−0.0044 (8)	0.0091 (8)	0.0017 (8)
C13	0.0467 (10)	0.0520 (10)	0.0400 (10)	−0.0016 (8)	0.0132 (8)	0.0029 (8)
C14	0.0672 (13)	0.0661 (12)	0.0422 (10)	−0.0091 (9)	0.0171 (9)	0.0008 (8)
C15	0.0621 (12)	0.0674 (13)	0.0461 (11)	−0.0079 (10)	0.0008 (9)	−0.0017 (9)

Cl1—C4	1.7365 (17)	C8—C13	1.389 (2)
O1—C1	1.336 (2)	C9—C10	1.386 (2)
O1—H1	0.8200	C9—H9	0.9300
N1—C7	1.267 (2)	C10—C11	1.396 (2)
N1—C8	1.422 (2)	C10—C14	1.505 (2)
C1—C6	1.387 (2)	C11—C12	1.385 (2)
C1—C2	1.401 (2)	C11—C15	1.500 (2)
C2—C3	1.391 (2)	C12—C13	1.372 (2)
C2—C7	1.452 (2)	C12—H12	0.9300
C3—C4	1.372 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.375 (2)	C14—H14B	0.9600
C5—C6	1.368 (2)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C8—C9	1.379 (2)
C1—O1—H1	109.5	C8—C9—H9	118.9
C7—N1—C8	122.85 (15)	C10—C9—H9	118.9
O1—C1—C6	118.44 (15)	C9—C10—C11	118.83 (15)
O1—C1—C2	122.14 (15)	C9—C10—C14	120.27 (16)
C6—C1—C2	119.42 (15)	C11—C10—C14	120.89 (15)
C3—C2—C1	119.12 (15)	C12—C11—C10	118.45 (15)
C3—C2—C7	119.72 (15)	C12—C11—C15	120.34 (16)
C1—C2—C7	121.15 (15)	C10—C11—C15	121.20 (16)
C4—C3—C2	120.07 (16)	C13—C12—C11	122.41 (16)
C4—C3—H3	120.0	C13—C12—H12	118.8
C2—C3—H3	120.0	C11—C12—H12	118.8
C3—C4—C5	120.82 (16)	C12—C13—C8	119.34 (15)
C3—C4—Cl1	119.80 (14)	C12—C13—H13	120.3
C5—C4—Cl1	119.37 (13)	C8—C13—H13	120.3
C6—C5—C4	119.86 (16)	C10—C14—H14A	109.5
C6—C5—H5	120.1	C10—C14—H14B	109.5
C4—C5—H5	120.1	H14A—C14—H14B	109.5
C5—C6—C1	120.69 (16)	C10—C14—H14C	109.5
C5—C6—H6	119.7	H14A—C14—H14C	109.5
C1—C6—H6	119.7	H14B—C14—H14C	109.5
N1—C7—C2	121.73 (16)	C11—C15—H15A	109.5
N1—C7—H7	119.1	C11—C15—H15B	109.5
C2—C7—H7	119.1	H15A—C15—H15B	109.5
C9—C8—C13	118.75 (15)	C11—C15—H15C	109.5
C9—C8—N1	116.19 (14)	H15A—C15—H15C	109.5
C13—C8—N1	125.06 (14)	H15B—C15—H15C	109.5
C8—C9—C10	122.23 (15)
O1—C1—C2—C3	178.21 (15)	C7—N1—C8—C9	−178.57 (14)
C6—C1—C2—C3	−1.3 (2)	C7—N1—C8—C13	1.2 (3)
O1—C1—C2—C7	−0.9 (3)	C13—C8—C9—C10	0.4 (2)
C6—C1—C2—C7	179.60 (15)	N1—C8—C9—C10	−179.85 (13)
C1—C2—C3—C4	0.4 (2)	C8—C9—C10—C11	0.3 (2)
C7—C2—C3—C4	179.50 (14)	C8—C9—C10—C14	179.07 (14)
C2—C3—C4—C5	0.5 (3)	C9—C10—C11—C12	−0.8 (2)
C2—C3—C4—Cl1	−178.37 (12)	C14—C10—C11—C12	−179.62 (15)
C3—C4—C5—C6	−0.4 (3)	C9—C10—C11—C15	178.03 (15)
Cl1—C4—C5—C6	178.42 (13)	C14—C10—C11—C15	−0.7 (2)
C4—C5—C6—C1	−0.5 (3)	C10—C11—C12—C13	0.8 (3)
O1—C1—C6—C5	−178.16 (16)	C15—C11—C12—C13	−178.10 (15)
C2—C1—C6—C5	1.4 (3)	C11—C12—C13—C8	−0.1 (3)
C8—N1—C7—C2	−179.54 (13)	C9—C8—C13—C12	−0.5 (2)
C3—C2—C7—N1	−178.66 (14)	N1—C8—C13—C12	179.79 (15)
C1—C2—C7—N1	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.5998 (19)	149
C3—H3···Cg1i	0.93	2.98	3.732 (2)	139
C6—H6···Cg2ii	0.93	2.93	3.576 (2)	128
C14—H14B···Cg2iii	0.96	2.96	3.656 (2)	131

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of the C1C6 and C8C13 benzene rings, respectively.

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.87	2.5998(19)	149
C3H3Cg1i	0.93	2.98	3.732(2)	139
C6H6Cg2ii	0.93	2.93	3.576(2)	128
C14H14B Cg2iii	0.96	2.96	3.656(2)	131

Symmetry codes: (i) ; (ii) ; (iii) .