(E)-2,4-Dichloro-6-{1-[(2-chloro-eth-yl)imino]-eth-yl}phenol.

The title Schiff base compound, C(10)H(10)Cl(3)NO, was prepared by the condensation of 1-(3,5-dichloro-2-hy-droxy-phen-yl)ethanone with chloro-ethyl-amine. The imine adopts an E configuration with respect to the C=N bond. The H atom of the phenolic OH group is disordered over two positions with site occupation factors of 0.52 (7) and 0.48 (7), respectively, and the major occupancy component is involved in an intramolecular N-H⋯O hydrogen bond. The compound therefore exists in an iminium-phenolate as well as in the imino-phenol form. In the crystal, mol-ecules are connected by C-H⋯O and C-H⋯Cl hydrogen bonds and Cl⋯Cl inter-actions [3.7864 (9) Å] into a three-dimensional network. In addition, inter-molecular π-π stacking inter-actions [centroid-centroid distance = 4.4312 (9) Å] are observed.

Related literature

For a related structure, see: Wang et al. (2010 ▶). For applications of Schiff base ligands, see: Yin et al. (2004 ▶); Böhme & Günther (2007 ▶).

Experimental

Crystal data

C10H10Cl3NO

M = 266.54

Monoclinic,

a = 14.5710 (2) Å

b = 10.2323 (2) Å

c = 7.7384 (1) Å

β = 94.376 (1)°

V = 1150.39 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.77 mm−1

T = 296 K

0.38 × 0.19 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.762, T max = 0.951

8253 measured reflections

2625 independent reflections

1940 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.02

2625 reflections

146 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004448X/im2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004448X/im2238Isup2.hkl

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

C10H10Cl3NO	F(000) = 544
Mr = 266.54	Dx = 1.539 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2504 reflections
a = 14.5710 (2) Å	θ = 2.4–25.9°
b = 10.2323 (2) Å	µ = 0.77 mm−1
c = 7.7384 (1) Å	T = 296 K
β = 94.376 (1)°	Plate, orange
V = 1150.39 (3) Å3	0.38 × 0.19 × 0.07 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2625 independent reflections
Radiation source: fine-focus sealed tube	1940 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −18→17
Tmin = 0.762, Tmax = 0.951	k = −10→13
8253 measured reflections	l = −8→10

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.1559P] where P = (Fo2 + 2Fc2)/3
2625 reflections	(Δ/σ)max = 0.006
146 parameters	Δρmax = 0.25 e Å−3
2 restraints	Δρmin = −0.21 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	Occ. (<1)
C1	0.57736 (13)	0.15817 (19)	−0.1505 (2)	0.0498 (4)
C2	0.61146 (13)	0.0340 (2)	−0.1143 (2)	0.0516 (5)
H2	0.5771	−0.0395	−0.1481	0.062*
C3	0.69659 (12)	0.02119 (17)	−0.0279 (2)	0.0455 (4)
C4	0.75065 (12)	0.12988 (16)	0.0289 (2)	0.0401 (4)
C5	0.71381 (12)	0.25627 (16)	−0.0117 (2)	0.0388 (4)
C6	0.62665 (12)	0.26726 (18)	−0.1027 (2)	0.0458 (4)
H6	0.6026	0.3495	−0.1303	0.055*
C7	0.76729 (12)	0.37256 (16)	0.0405 (2)	0.0403 (4)
C8	0.73432 (14)	0.50736 (18)	−0.0072 (3)	0.0559 (5)
H8A	0.6689	0.5122	0.0002	0.084*
H8B	0.7487	0.5268	−0.1235	0.084*
H8C	0.7642	0.5696	0.0710	0.084*
C9	0.90715 (13)	0.45820 (17)	0.1910 (2)	0.0491 (4)
H9A	0.8749	0.5189	0.2611	0.059*
H9B	0.9276	0.5057	0.0925	0.059*
C10	0.98893 (13)	0.40380 (19)	0.2962 (2)	0.0509 (5)
H10A	0.9682	0.3582	0.3961	0.061*
H10B	1.0284	0.4752	0.3382	0.061*
Cl1	0.46922 (4)	0.17442 (7)	−0.26165 (8)	0.0791 (2)
Cl2	0.74236 (4)	−0.13318 (4)	0.01161 (8)	0.06643 (18)
Cl3	1.05345 (3)	0.29415 (5)	0.17400 (7)	0.05817 (16)
N1	0.84464 (10)	0.35378 (14)	0.12961 (19)	0.0418 (3)
H1N	0.858 (3)	0.271 (2)	0.146 (5)	0.049 (16)*	0.52 (7)
H1O	0.855 (3)	0.183 (3)	0.145 (6)	0.07 (2)*	0.48 (7)
O1	0.83069 (9)	0.11256 (12)	0.11379 (18)	0.0494 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0381 (10)	0.0583 (11)	0.0523 (10)	−0.0039 (9)	−0.0005 (8)	0.0049 (9)
C2	0.0472 (11)	0.0491 (10)	0.0583 (11)	−0.0119 (9)	0.0041 (9)	−0.0039 (9)
C3	0.0451 (10)	0.0370 (9)	0.0551 (10)	−0.0010 (8)	0.0077 (8)	−0.0016 (7)
C4	0.0392 (10)	0.0368 (8)	0.0450 (9)	−0.0005 (7)	0.0069 (7)	−0.0006 (7)
C5	0.0387 (9)	0.0364 (8)	0.0417 (9)	−0.0005 (7)	0.0051 (7)	0.0023 (7)
C6	0.0421 (10)	0.0449 (10)	0.0506 (10)	0.0042 (8)	0.0041 (8)	0.0077 (8)
C7	0.0428 (10)	0.0360 (8)	0.0428 (9)	0.0027 (7)	0.0081 (7)	0.0028 (7)
C8	0.0577 (12)	0.0382 (9)	0.0709 (12)	0.0041 (9)	−0.0014 (10)	0.0076 (9)
C9	0.0515 (11)	0.0348 (8)	0.0610 (11)	−0.0068 (8)	0.0040 (9)	−0.0030 (8)
C10	0.0561 (12)	0.0511 (10)	0.0450 (9)	−0.0121 (9)	0.0002 (8)	−0.0071 (8)
Cl1	0.0484 (3)	0.0859 (4)	0.0987 (4)	−0.0121 (3)	−0.0218 (3)	0.0179 (3)
Cl2	0.0629 (4)	0.0339 (2)	0.1020 (4)	0.0003 (2)	0.0030 (3)	−0.0027 (2)
Cl3	0.0544 (3)	0.0519 (3)	0.0673 (3)	0.0025 (2)	−0.0016 (2)	−0.0059 (2)
N1	0.0448 (9)	0.0310 (7)	0.0493 (8)	−0.0020 (6)	0.0019 (7)	−0.0003 (6)
O1	0.0408 (7)	0.0350 (7)	0.0710 (8)	0.0018 (6)	−0.0055 (6)	0.0007 (6)

C1—C6	1.363 (3)	C7—C8	1.498 (2)
C1—C2	1.385 (3)	C8—H8A	0.9600
C1—Cl1	1.7446 (19)	C8—H8B	0.9600
C2—C3	1.370 (2)	C8—H8C	0.9600
C2—H2	0.9300	C9—N1	1.460 (2)
C3—C4	1.413 (2)	C9—C10	1.498 (3)
C3—Cl2	1.7326 (18)	C9—H9A	0.9700
C4—O1	1.306 (2)	C9—H9B	0.9700
C4—C5	1.426 (2)	C10—Cl3	1.781 (2)
C5—C6	1.409 (2)	C10—H10A	0.9700
C5—C7	1.462 (2)	C10—H10B	0.9700
C6—H6	0.9300	N1—H1N	0.874 (19)
C7—N1	1.290 (2)	O1—H1O	0.827 (19)
C6—C1—C2	121.53 (17)	C7—C8—H8B	109.5
C6—C1—Cl1	119.55 (15)	H8A—C8—H8B	109.5
C2—C1—Cl1	118.92 (15)	C7—C8—H8C	109.5
C3—C2—C1	118.94 (17)	H8A—C8—H8C	109.5
C3—C2—H2	120.5	H8B—C8—H8C	109.5
C1—C2—H2	120.5	N1—C9—C10	110.83 (15)
C2—C3—C4	122.61 (16)	N1—C9—H9A	109.5
C2—C3—Cl2	119.69 (14)	C10—C9—H9A	109.5
C4—C3—Cl2	117.69 (13)	N1—C9—H9B	109.5
O1—C4—C3	120.31 (15)	C10—C9—H9B	109.5
O1—C4—C5	122.71 (15)	H9A—C9—H9B	108.1
C3—C4—C5	116.98 (15)	C9—C10—Cl3	112.06 (12)
C6—C5—C4	119.49 (16)	C9—C10—H10A	109.2
C6—C5—C7	120.94 (15)	Cl3—C10—H10A	109.2
C4—C5—C7	119.56 (15)	C9—C10—H10B	109.2
C1—C6—C5	120.43 (17)	Cl3—C10—H10B	109.2
C1—C6—H6	119.8	H10A—C10—H10B	107.9
C5—C6—H6	119.8	C7—N1—C9	124.26 (15)
N1—C7—C5	116.87 (14)	C7—N1—H1N	113 (3)
N1—C7—C8	121.32 (16)	C9—N1—H1N	122 (3)
C5—C7—C8	121.82 (16)	C4—O1—H1O	112 (4)
C7—C8—H8A	109.5
C6—C1—C2—C3	0.2 (3)	C2—C1—C6—C5	−1.1 (3)
Cl1—C1—C2—C3	179.64 (14)	Cl1—C1—C6—C5	179.53 (13)
C1—C2—C3—C4	1.1 (3)	C4—C5—C6—C1	0.5 (3)
C1—C2—C3—Cl2	−177.60 (14)	C7—C5—C6—C1	−179.91 (16)
C2—C3—C4—O1	178.66 (16)	C6—C5—C7—N1	177.17 (15)
Cl2—C3—C4—O1	−2.6 (2)	C4—C5—C7—N1	−3.3 (2)
C2—C3—C4—C5	−1.6 (3)	C6—C5—C7—C8	−3.0 (3)
Cl2—C3—C4—C5	177.17 (12)	C4—C5—C7—C8	176.56 (16)
O1—C4—C5—C6	−179.54 (15)	N1—C9—C10—Cl3	60.56 (18)
C3—C4—C5—C6	0.7 (2)	C5—C7—N1—C9	179.36 (15)
O1—C4—C5—C7	0.9 (3)	C8—C7—N1—C9	−0.5 (3)
C3—C4—C5—C7	−178.81 (15)	C10—C9—N1—C7	177.78 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.88 (2)	1.68 (2)	2.479 (2)	150 (4)
C10—H10B···O1i	0.97	2.48	3.416 (2)	159
C10—H10A···Cl3ii	0.97	2.86	3.621 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.88 (2)	1.68 (2)	2.479 (2)	150 (4)
C10—H10B⋯O1i	0.97	2.48	3.416 (2)	159
C10—H10A⋯Cl3ii	0.97	2.86	3.621 (2)	136

Symmetry codes: (i) ; (ii) .