2-[(3,4-Di-chloro-benzyl-idene)amino]-4-methyl-phenol.

In the title compound, C14H11Cl2NO, the dihedral angle between the benzene rings is 15.36 (8)°. A phenol-imine-type intra-molecular O-H⋯N hydrogen bond generates an S(5) ring motif. In the crystal, a pair of weak C-H⋯O hydrogen bonds form an R 2 (1)(7) ring motif involving glide-plane-related mol-ecules. The mol-ecules linked via these inter-actions form chains along [101].

Related literature

For Schiff bases, see: Akine & Nabeshima (2009 ▶); Vigato & Tamburini (2004 ▶). For related structures, see: Efil et al. (2012 ▶); Fridman & Kaftory (2007 ▶); Jiao et al. (2006 ▶); Wang & Wang (2007 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H11Cl2NO

M = 280.14

Monoclinic,

a = 4.6074 (7) Å

b = 21.680 (3) Å

c = 12.7907 (18) Å

β = 93.342 (2)°

V = 1275.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 150 K

0.64 × 0.14 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2009 ▶) T min = 0.743, T max = 0.966

12828 measured reflections

3159 independent reflections

2556 reflections with I2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.02

3159 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013585/fy2096sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013585/fy2096Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013585/fy2096Isup3.cml

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

C14H11Cl2NO	F(000) = 576
Mr = 280.14	Dx = 1.459 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3681 reflections
a = 4.6074 (7) Å	θ = 2.5–28.0°
b = 21.680 (3) Å	µ = 0.49 mm−1
c = 12.7907 (18) Å	T = 150 K
β = 93.342 (2)°	Block, yellow
V = 1275.5 (3) Å3	0.64 × 0.14 × 0.07 mm
Z = 4

Bruker APEXII CCD diffractometer	3159 independent reflections
Radiation source: fine-focus sealed tube	2556 reflections with I2σ(I)
Graphite monochromator	Rint = 0.032
ω rotation with narrow frames scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2009)	h = −6→6
Tmin = 0.743, Tmax = 0.966	k = −28→28
12828 measured reflections	l = −17→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.3141P] where P = (Fo2 + 2Fc2)/3
3159 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.23 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	0.62127 (9)	0.968261 (19)	0.61947 (3)	0.03521 (12)
N1	−0.1214 (3)	0.79478 (6)	0.73732 (10)	0.0234 (3)
O1	−0.4296 (3)	0.77697 (6)	0.55736 (9)	0.0381 (3)
H1	−0.2991	0.7997	0.5779	0.057*
C1	−0.4801 (3)	0.73837 (7)	0.63921 (12)	0.0264 (3)
Cl2	0.86902 (8)	1.020614 (17)	0.83841 (3)	0.03076 (12)
C2	−0.6873 (4)	0.69200 (8)	0.62554 (13)	0.0321 (4)
H2	−0.7926	0.6872	0.5600	0.039*
C3	−0.7391 (3)	0.65297 (7)	0.70787 (14)	0.0322 (4)
H3	−0.8816	0.6215	0.6982	0.039*
C4	−0.5859 (3)	0.65887 (7)	0.80533 (13)	0.0297 (3)
C5	−0.3799 (3)	0.70580 (7)	0.81783 (12)	0.0261 (3)
H5	−0.2752	0.7107	0.8835	0.031*
C6	−0.3245 (3)	0.74577 (7)	0.73566 (11)	0.0228 (3)
C7	−0.6423 (4)	0.61546 (8)	0.89403 (15)	0.0406 (4)
H7A	−0.5103	0.6252	0.9546	0.061*
H7B	−0.6092	0.5729	0.8718	0.061*
H7C	−0.8439	0.6200	0.9133	0.061*
C8	0.0181 (3)	0.81112 (7)	0.82195 (12)	0.0235 (3)
H8	−0.0153	0.7899	0.8851	0.028*
C9	0.2291 (3)	0.86195 (7)	0.82415 (11)	0.0216 (3)
C10	0.3150 (3)	0.88903 (7)	0.73156 (12)	0.0233 (3)
H10	0.2364	0.8745	0.6658	0.028*
C11	0.5146 (3)	0.93697 (7)	0.73568 (11)	0.0235 (3)
C12	0.6295 (3)	0.95870 (7)	0.83241 (12)	0.0233 (3)
C13	0.5479 (3)	0.93173 (7)	0.92445 (12)	0.0245 (3)
H13	0.6282	0.9461	0.9901	0.029*
C14	0.3485 (3)	0.88372 (7)	0.92030 (12)	0.0239 (3)
H14	0.2924	0.8654	0.9835	0.029*

	U11	U22	U33	U12	U13	U23
Cl1	0.0427 (3)	0.0358 (2)	0.0276 (2)	−0.00705 (17)	0.00626 (17)	0.00436 (15)
N1	0.0204 (6)	0.0227 (6)	0.0268 (6)	−0.0010 (5)	−0.0001 (5)	−0.0005 (5)
O1	0.0430 (7)	0.0457 (7)	0.0249 (6)	−0.0154 (6)	−0.0044 (5)	0.0008 (5)
C1	0.0253 (8)	0.0272 (8)	0.0270 (8)	−0.0017 (6)	0.0029 (6)	−0.0035 (6)
Cl2	0.0272 (2)	0.0259 (2)	0.0390 (2)	−0.00604 (14)	0.00070 (15)	−0.00215 (15)
C2	0.0267 (8)	0.0361 (9)	0.0332 (9)	−0.0049 (7)	−0.0002 (6)	−0.0109 (7)
C3	0.0243 (8)	0.0262 (8)	0.0466 (10)	−0.0060 (6)	0.0076 (7)	−0.0110 (7)
C4	0.0276 (8)	0.0223 (7)	0.0403 (9)	−0.0003 (6)	0.0102 (7)	−0.0023 (6)
C5	0.0247 (7)	0.0237 (7)	0.0299 (8)	0.0007 (6)	0.0016 (6)	−0.0017 (6)
C6	0.0188 (7)	0.0219 (7)	0.0279 (8)	−0.0002 (5)	0.0026 (6)	−0.0040 (6)
C7	0.0455 (11)	0.0269 (9)	0.0508 (11)	−0.0042 (7)	0.0135 (9)	0.0033 (8)
C8	0.0206 (7)	0.0239 (7)	0.0258 (7)	0.0006 (5)	0.0007 (5)	0.0012 (6)
C9	0.0179 (7)	0.0214 (7)	0.0252 (7)	0.0024 (5)	−0.0003 (5)	−0.0003 (5)
C10	0.0219 (7)	0.0239 (7)	0.0237 (7)	0.0016 (5)	−0.0018 (5)	−0.0020 (6)
C11	0.0234 (7)	0.0228 (7)	0.0246 (7)	0.0037 (6)	0.0037 (6)	0.0027 (6)
C12	0.0187 (7)	0.0199 (7)	0.0311 (8)	0.0011 (5)	0.0003 (6)	−0.0012 (6)
C13	0.0228 (7)	0.0260 (7)	0.0241 (7)	0.0015 (6)	−0.0031 (6)	−0.0027 (6)
C14	0.0219 (7)	0.0260 (7)	0.0234 (7)	0.0017 (6)	−0.0014 (5)	0.0020 (6)

Cl1—C11	1.7310 (15)	C5—H5	0.9500
N1—C8	1.2766 (19)	C7—H7A	0.9800
N1—C6	1.4153 (19)	C7—H7B	0.9800
O1—C1	1.3708 (19)	C7—H7C	0.9800
O1—H1	0.8089	C8—C9	1.469 (2)
C1—C2	1.390 (2)	C8—H8	0.9500
C1—C6	1.399 (2)	C9—C10	1.399 (2)
Cl2—C12	1.7366 (15)	C9—C14	1.400 (2)
C2—C3	1.382 (2)	C10—C11	1.387 (2)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.402 (2)	C11—C12	1.399 (2)
C3—H3	0.9500	C12—C13	1.386 (2)
C4—C5	1.394 (2)	C13—C14	1.387 (2)
C4—C7	1.508 (2)	C13—H13	0.9500
C5—C6	1.397 (2)	C14—H14	0.9500
C8—N1—C6	121.40 (13)	H7A—C7—H7C	109.5
C1—O1—H1	106.3	H7B—C7—H7C	109.5
O1—C1—C2	119.44 (14)	N1—C8—C9	121.64 (14)
O1—C1—C6	120.14 (13)	N1—C8—H8	119.2
C2—C1—C6	120.42 (15)	C9—C8—H8	119.2
C3—C2—C1	119.65 (15)	C10—C9—C14	119.09 (13)
C3—C2—H2	120.2	C10—C9—C8	121.20 (13)
C1—C2—H2	120.2	C14—C9—C8	119.71 (13)
C2—C3—C4	121.39 (15)	C11—C10—C9	120.12 (13)
C2—C3—H3	119.3	C11—C10—H10	119.9
C4—C3—H3	119.3	C9—C10—H10	119.9
C5—C4—C3	118.21 (15)	N1i—C10—H10	94.2
C5—C4—C7	121.01 (16)	C10—C11—C12	120.13 (14)
C3—C4—C7	120.79 (15)	C10—C11—Cl1	118.82 (11)
C4—C5—C6	121.28 (15)	C12—C11—Cl1	121.04 (12)
C4—C5—H5	119.4	C13—C12—C11	120.12 (14)
C6—C5—H5	119.4	C13—C12—Cl2	119.45 (11)
C5—C6—C1	119.04 (14)	C11—C12—Cl2	120.41 (12)
C5—C6—N1	127.15 (13)	C12—C13—C14	119.73 (14)
C1—C6—N1	113.81 (13)	C12—C13—H13	120.1
C4—C7—H7A	109.5	C14—C13—H13	120.1
C4—C7—H7B	109.5	C13—C14—C9	120.80 (14)
H7A—C7—H7B	109.5	C13—C14—H14	119.6
C4—C7—H7C	109.5	C9—C14—H14	119.6
O1—C1—C2—C3	−179.97 (15)	N1—C8—C9—C10	−8.8 (2)
C6—C1—C2—C3	−0.1 (2)	N1—C8—C9—C14	171.57 (14)
C1—C2—C3—C4	−0.3 (2)	C14—C9—C10—C11	−0.3 (2)
C2—C3—C4—C5	0.6 (2)	C8—C9—C10—C11	180.00 (13)
C2—C3—C4—C7	−179.26 (15)	C9—C10—C11—C12	−0.4 (2)
C3—C4—C5—C6	−0.5 (2)	C9—C10—C11—Cl1	178.69 (11)
C7—C4—C5—C6	179.34 (15)	C10—C11—C12—C13	1.1 (2)
C4—C5—C6—C1	0.1 (2)	Cl1—C11—C12—C13	−178.00 (11)
C4—C5—C6—N1	−179.53 (14)	C10—C11—C12—Cl2	−177.57 (11)
O1—C1—C6—C5	−179.95 (14)	Cl1—C11—C12—Cl2	3.38 (18)
C2—C1—C6—C5	0.2 (2)	C11—C12—C13—C14	−1.0 (2)
O1—C1—C6—N1	−0.2 (2)	Cl2—C12—C13—C14	177.67 (11)
C2—C1—C6—N1	179.88 (14)	C12—C13—C14—C9	0.2 (2)
C8—N1—C6—C5	−6.9 (2)	C10—C9—C14—C13	0.4 (2)
C8—N1—C6—C1	173.46 (14)	C8—C9—C14—C13	−179.91 (13)
C6—N1—C8—C9	−179.98 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ii	0.95	2.67	3.618 (2)	174
C8—H8···O1ii	0.95	2.65	3.562 (2)	162
O1—H1···N1	0.81	2.16	2.6612 (17)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.67	3.618 (2)	174
C8—H8⋯O1i	0.95	2.65	3.562 (2)	162
O1—H1⋯N1	0.81	2.16	2.6612 (17)	121

Symmetry code: (i) .