2-[(E)-(2,4,6-Trichloro-phen-yl)imino-meth-yl]phenol.

The title mol-ecule, C(13)H(8)Cl(3)NO, exists in a trans configuration with respect to the C=N bond [1.278 (2) Å]. The benzene rings form a dihedral angle of 24.64 (11)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. In the crystal, π-π stacking inter-actions [centroid-centroid distances = 3.6893 (14) Å] are observed.

Related literature

For general background to and the pharmacological activity of Schiff base compounds, see: Shapiro (1998 ▶); Villar et al. (2004 ▶); Venugopal & Jayashree (2008 ▶); Pandey et al. (2003 ▶); Bhat et al. (2005 ▶); Wadher et al. (2009 ▶). For related structures, see: Fun et al. (2011a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H8Cl3NO

M = 300.55

Monoclinic,

a = 12.8847 (16) Å

b = 6.9505 (9) Å

c = 14.4265 (18) Å

β = 96.612 (2)°

V = 1283.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 296 K

0.36 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.785, T max = 0.908

10136 measured reflections

3782 independent reflections

2586 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.02

3782 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026122/lh5276sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026122/lh5276Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026122/lh5276Isup3.cml

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

C13H8Cl3NO	F(000) = 608
Mr = 300.55	Dx = 1.556 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3223 reflections
a = 12.8847 (16) Å	θ = 2.9–30.0°
b = 6.9505 (9) Å	µ = 0.70 mm−1
c = 14.4265 (18) Å	T = 296 K
β = 96.612 (2)°	Block, yellow
V = 1283.4 (3) Å3	0.36 × 0.19 × 0.14 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	3782 independent reflections
Radiation source: fine-focus sealed tube	2586 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 30.2°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.785, Tmax = 0.908	k = −9→9
10136 measured reflections	l = −20→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0489P)2 + 0.6136P] where P = (Fo2 + 2Fc2)/3
3782 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.05175 (4)	0.34050 (9)	0.92951 (3)	0.05264 (16)
Cl2	0.44455 (4)	0.27949 (11)	0.84597 (5)	0.0669 (2)
Cl3	0.35845 (4)	0.16620 (13)	0.63858 (4)	0.0723 (2)
O1	−0.20343 (13)	0.2343 (3)	0.77771 (11)	0.0562 (4)
N1	−0.01212 (11)	0.2621 (2)	0.73161 (11)	0.0370 (3)
C1	0.13702 (14)	0.3001 (3)	0.84736 (13)	0.0368 (4)
C2	0.24358 (14)	0.3061 (3)	0.87539 (14)	0.0427 (4)
H2A	0.2685	0.3344	0.9369	0.051*
C3	0.31237 (14)	0.2693 (3)	0.81056 (15)	0.0428 (4)
C4	0.27450 (14)	0.2244 (3)	0.71929 (14)	0.0427 (4)
C5	0.16785 (14)	0.2223 (3)	0.69162 (13)	0.0408 (4)
H5A	0.1432	0.1931	0.6301	0.049*
C6	0.09726 (13)	0.2636 (3)	0.75513 (12)	0.0346 (4)
C7	−0.05235 (13)	0.3079 (3)	0.64944 (13)	0.0372 (4)
H7A	−0.0084	0.3437	0.6056	0.045*
C8	−0.16440 (14)	0.3060 (3)	0.62241 (14)	0.0387 (4)
C9	−0.20251 (16)	0.3408 (4)	0.52901 (15)	0.0514 (5)
H9A	−0.1558	0.3640	0.4857	0.062*
C10	−0.30845 (17)	0.3411 (4)	0.50043 (18)	0.0628 (7)
H10A	−0.3333	0.3623	0.4382	0.075*
C11	−0.37712 (17)	0.3093 (4)	0.56579 (19)	0.0638 (7)
H11A	−0.4486	0.3109	0.5471	0.077*
C12	−0.34176 (16)	0.2754 (4)	0.65778 (19)	0.0561 (6)
H12A	−0.3893	0.2549	0.7006	0.067*
C13	−0.23490 (15)	0.2716 (3)	0.68736 (15)	0.0430 (4)
H1O1	−0.142 (2)	0.238 (5)	0.787 (2)	0.077 (10)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0521 (3)	0.0677 (4)	0.0399 (2)	0.0004 (3)	0.0130 (2)	−0.0002 (2)
Cl2	0.0322 (2)	0.0865 (5)	0.0786 (4)	−0.0046 (3)	−0.0083 (2)	0.0036 (3)
Cl3	0.0415 (3)	0.1152 (6)	0.0624 (4)	0.0192 (3)	0.0154 (2)	−0.0023 (4)
O1	0.0452 (8)	0.0715 (12)	0.0537 (9)	0.0035 (8)	0.0128 (7)	0.0064 (8)
N1	0.0303 (7)	0.0408 (9)	0.0400 (8)	0.0040 (6)	0.0037 (6)	−0.0019 (7)
C1	0.0366 (8)	0.0376 (10)	0.0365 (8)	−0.0005 (8)	0.0054 (7)	0.0016 (8)
C2	0.0388 (9)	0.0464 (12)	0.0407 (9)	−0.0037 (8)	−0.0044 (7)	0.0007 (8)
C3	0.0300 (8)	0.0448 (11)	0.0518 (11)	−0.0015 (8)	−0.0036 (7)	0.0060 (9)
C4	0.0319 (8)	0.0509 (12)	0.0459 (10)	0.0077 (8)	0.0070 (7)	0.0037 (9)
C5	0.0337 (8)	0.0502 (12)	0.0379 (9)	0.0065 (8)	0.0012 (7)	−0.0009 (8)
C6	0.0291 (7)	0.0349 (9)	0.0396 (9)	0.0009 (7)	0.0032 (6)	0.0000 (7)
C7	0.0309 (8)	0.0399 (10)	0.0411 (9)	0.0031 (7)	0.0049 (7)	−0.0029 (8)
C8	0.0305 (8)	0.0391 (10)	0.0460 (9)	0.0031 (7)	0.0020 (7)	−0.0049 (8)
C9	0.0404 (10)	0.0649 (15)	0.0473 (10)	0.0039 (10)	−0.0016 (8)	−0.0046 (10)
C10	0.0443 (11)	0.0808 (19)	0.0592 (13)	0.0061 (11)	−0.0114 (10)	−0.0079 (13)
C11	0.0352 (10)	0.0735 (18)	0.0790 (17)	0.0022 (11)	−0.0098 (10)	−0.0134 (14)
C12	0.0346 (9)	0.0597 (15)	0.0752 (15)	−0.0016 (10)	0.0109 (10)	−0.0075 (12)
C13	0.0360 (9)	0.0391 (11)	0.0544 (11)	0.0025 (8)	0.0072 (8)	−0.0047 (9)

Cl1—C1	1.7292 (19)	C5—H5A	0.9300
Cl2—C3	1.7222 (18)	C7—C8	1.452 (2)
Cl3—C4	1.726 (2)	C7—H7A	0.9300
O1—C13	1.345 (3)	C8—C13	1.399 (3)
O1—H1O1	0.79 (3)	C8—C9	1.401 (3)
N1—C7	1.278 (2)	C9—C10	1.380 (3)
N1—C6	1.411 (2)	C9—H9A	0.9300
C1—C2	1.387 (2)	C10—C11	1.383 (4)
C1—C6	1.393 (2)	C10—H10A	0.9300
C2—C3	1.384 (3)	C11—C12	1.373 (4)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.386 (3)	C12—C13	1.394 (3)
C4—C5	1.386 (2)	C12—H12A	0.9300
C5—C6	1.393 (2)
C13—O1—H1O1	110 (2)	N1—C7—H7A	119.0
C7—N1—C6	120.55 (16)	C8—C7—H7A	119.0
C2—C1—C6	121.80 (17)	C13—C8—C9	119.42 (18)
C2—C1—Cl1	118.76 (14)	C13—C8—C7	121.61 (18)
C6—C1—Cl1	119.44 (13)	C9—C8—C7	118.97 (18)
C3—C2—C1	119.14 (17)	C10—C9—C8	120.8 (2)
C3—C2—H2A	120.4	C10—C9—H9A	119.6
C1—C2—H2A	120.4	C8—C9—H9A	119.6
C2—C3—C4	120.04 (17)	C9—C10—C11	119.0 (2)
C2—C3—Cl2	118.70 (15)	C9—C10—H10A	120.5
C4—C3—Cl2	121.26 (16)	C11—C10—H10A	120.5
C3—C4—C5	120.32 (18)	C12—C11—C10	121.3 (2)
C3—C4—Cl3	120.94 (15)	C12—C11—H11A	119.4
C5—C4—Cl3	118.73 (15)	C10—C11—H11A	119.4
C4—C5—C6	120.60 (17)	C11—C12—C13	120.4 (2)
C4—C5—H5A	119.7	C11—C12—H12A	119.8
C6—C5—H5A	119.7	C13—C12—H12A	119.8
C1—C6—C5	118.01 (16)	O1—C13—C12	118.5 (2)
C1—C6—N1	118.57 (16)	O1—C13—C8	122.39 (18)
C5—C6—N1	123.37 (16)	C12—C13—C8	119.1 (2)
N1—C7—C8	122.10 (17)
C6—C1—C2—C3	−1.9 (3)	C7—N1—C6—C1	151.17 (19)
Cl1—C1—C2—C3	178.45 (16)	C7—N1—C6—C5	−31.6 (3)
C1—C2—C3—C4	−0.9 (3)	C6—N1—C7—C8	179.28 (17)
C1—C2—C3—Cl2	179.37 (16)	N1—C7—C8—C13	6.2 (3)
C2—C3—C4—C5	2.1 (3)	N1—C7—C8—C9	−174.2 (2)
Cl2—C3—C4—C5	−178.18 (17)	C13—C8—C9—C10	−0.2 (4)
C2—C3—C4—Cl3	−176.72 (17)	C7—C8—C9—C10	−179.7 (2)
Cl2—C3—C4—Cl3	3.0 (3)	C8—C9—C10—C11	1.0 (4)
C3—C4—C5—C6	−0.5 (3)	C9—C10—C11—C12	−0.8 (4)
Cl3—C4—C5—C6	178.34 (16)	C10—C11—C12—C13	−0.3 (4)
C2—C1—C6—C5	3.4 (3)	C11—C12—C13—O1	−178.8 (2)
Cl1—C1—C6—C5	−176.92 (15)	C11—C12—C13—C8	1.1 (4)
C2—C1—C6—N1	−179.22 (18)	C9—C8—C13—O1	179.0 (2)
Cl1—C1—C6—N1	0.5 (3)	C7—C8—C13—O1	−1.5 (3)
C4—C5—C6—C1	−2.2 (3)	C9—C8—C13—C12	−0.9 (3)
C4—C5—C6—N1	−179.41 (19)	C7—C8—C13—C12	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.79 (3)	1.94 (3)	2.633 (2)	146 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.79 (3)	1.94 (3)	2.633 (2)	146 (3)