1,3,5-Trichloro-2-methoxy-benzene.

The meth-oxy group of the title compound, C(7)H(5)Cl(3)O, is rotated out of the plane of the aromatic ring system, with a dihedral angle of 84.11 (13)°, due to the two bulky ortho-chloro substituents.

Related literature

For similar structures of anisoles with two ortho-chloro substituents, see: Rissanen et al. (1987 ▶); Weller & Gerstner (1995 ▶); Wieczorek (1980 ▶). For other related literature, see: Brownlee et al. (1993 ▶); Curtis et al. (1972 ▶); Iimura et al. (1984 ▶); Kolehmainen & Knuutinen (1983 ▶); Oswald et al. (2005 ▶); Pereira et al. (2000 ▶); Rissanen et al. (1988 ▶); Vlachos et al. (2007 ▶); Zhang et al. (2006 ▶).

Experimental

Crystal data

C7H5Cl3O

M = 211.46

Monoclinic,

a = 14.7538 (5) Å

b = 3.9846 (2) Å

c = 15.4810 (7) Å

β = 115.5031 (19)°

V = 821.42 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.05 mm−1

T = 90.0 (2) K

0.25 × 0.25 × 0.12 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.780, T max = 0.885

13489 measured reflections

1888 independent reflections

1558 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.070

S = 1.13

1888 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.31 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 1994 ▶); software used to prepare material for publication: SHELX97 and local procedures.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800055X/om2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800055X/om2200Isup2.hkl

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

C7H5Cl3O	F000 = 424
Mr = 211.46	Dx = 1.710 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2156 reflections
a = 14.7538 (5) Å	θ = 1.0–27.5º
b = 3.9846 (2) Å	µ = 1.05 mm−1
c = 15.4810 (7) Å	T = 90.0 (2) K
β = 115.5031 (19)º	Block, colourless
V = 821.42 (6) Å3	0.25 × 0.25 × 0.12 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	1888 independent reflections
Radiation source: fine-focus sealed tube	1558 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
Detector resolution: 18 pixels mm-1	θmax = 27.5º
T = 90.0(2) K	θmin = 1.6º
ω scans at fixed χ = 55°	h = −18→19
Absorption correction: multi-scan(SCALEPACK; Otwinowski & Minor, 1997)	k = −5→5
Tmin = 0.780, Tmax = 0.885	l = −20→19
13489 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0244P)2 + 0.6499P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.001
1888 reflections	Δρmax = 0.35 e Å−3
101 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2σ(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	0.65436 (3)	0.31728 (13)	0.83292 (3)	0.02202 (13)
Cl2	0.36963 (3)	0.90882 (13)	0.91077 (3)	0.01965 (12)
Cl3	0.32350 (3)	0.84337 (13)	0.54775 (3)	0.02053 (13)
O1	0.51708 (9)	0.4751 (4)	0.63059 (9)	0.0189 (3)
C1	0.48575 (13)	0.5887 (5)	0.69659 (13)	0.0161 (4)
C2	0.54027 (13)	0.5242 (5)	0.79404 (13)	0.0161 (4)
C3	0.50643 (13)	0.6209 (5)	0.86111 (13)	0.0162 (4)
H3	0.5447	0.5753	0.9273	0.019*
C4	0.41531 (14)	0.7858 (5)	0.82874 (13)	0.0164 (4)
C5	0.35818 (13)	0.8564 (5)	0.73309 (13)	0.0158 (4)
H5	0.2958	0.9705	0.7126	0.019*
C6	0.39426 (13)	0.7561 (5)	0.66748 (12)	0.0147 (4)
C7	0.58710 (16)	0.6940 (6)	0.61549 (15)	0.0253 (5)
H7A	0.5565	0.9156	0.5951	0.038*
H7B	0.6039	0.5988	0.5659	0.038*
H7C	0.6483	0.7159	0.6753	0.038*

	U11	U22	U33	U12	U13	U23
Cl1	0.0146 (2)	0.0252 (3)	0.0231 (2)	0.00407 (19)	0.00509 (19)	−0.0021 (2)
Cl2	0.0178 (2)	0.0266 (3)	0.0163 (2)	0.00018 (18)	0.00906 (18)	−0.00204 (18)
Cl3	0.0190 (2)	0.0279 (3)	0.0139 (2)	0.00294 (19)	0.00632 (18)	0.00251 (18)
O1	0.0171 (7)	0.0230 (8)	0.0205 (7)	−0.0022 (6)	0.0119 (6)	−0.0046 (6)
C1	0.0160 (9)	0.0152 (10)	0.0188 (9)	−0.0037 (7)	0.0092 (7)	−0.0036 (7)
C2	0.0123 (8)	0.0142 (10)	0.0208 (9)	−0.0003 (7)	0.0061 (7)	−0.0008 (7)
C3	0.0152 (9)	0.0177 (10)	0.0129 (8)	−0.0030 (7)	0.0035 (7)	−0.0009 (7)
C4	0.0177 (9)	0.0160 (10)	0.0184 (9)	−0.0037 (7)	0.0106 (8)	−0.0031 (7)
C5	0.0128 (8)	0.0155 (10)	0.0192 (9)	−0.0002 (7)	0.0069 (7)	0.0005 (7)
C6	0.0138 (9)	0.0168 (10)	0.0120 (8)	−0.0023 (7)	0.0040 (7)	0.0002 (7)
C7	0.0273 (11)	0.0255 (11)	0.0310 (11)	−0.0054 (9)	0.0201 (9)	−0.0052 (9)

C1—O1	1.367 (2)	Cl3—C6	1.7264 (18)
C1—C2	1.394 (3)	C4—C5	1.381 (3)
C1—C6	1.395 (3)	C5—C6	1.393 (3)
C2—C3	1.386 (3)	C5—H5	0.9500
C2—Cl1	1.7329 (19)	O1—C7	1.446 (2)
C3—C4	1.382 (3)	C7—H7A	0.9800
C3—H3	0.9500	C7—H7B	0.9800
Cl2—C4	1.7447 (18)	C7—H7C	0.9800
O1—C1—C2	121.63 (16)	C4—C5—H5	120.8
O1—C1—C6	120.55 (16)	C6—C5—H5	120.8
C2—C1—C6	117.70 (16)	C5—C6—C1	121.46 (16)
C3—C2—C1	122.21 (17)	C5—C6—Cl3	118.74 (14)
C3—C2—Cl1	118.77 (14)	C1—C6—Cl3	119.79 (14)
C1—C2—Cl1	119.02 (14)	C1—O1—C7	114.60 (15)
C4—C3—C2	117.92 (17)	O1—C7—H7A	109.5
C4—C3—H3	121.0	O1—C7—H7B	109.5
C2—C3—H3	121.0	H7A—C7—H7B	109.5
C5—C4—C3	122.34 (17)	O1—C7—H7C	109.5
C5—C4—Cl2	118.33 (14)	H7A—C7—H7C	109.5
C3—C4—Cl2	119.33 (14)	H7B—C7—H7C	109.5
C4—C5—C6	118.36 (17)
O1—C1—C2—C3	−176.17 (17)	Cl2—C4—C5—C6	−179.55 (14)
C6—C1—C2—C3	−0.1 (3)	C4—C5—C6—C1	−0.1 (3)
O1—C1—C2—Cl1	4.0 (3)	C4—C5—C6—Cl3	−179.94 (14)
C6—C1—C2—Cl1	−179.91 (14)	O1—C1—C6—C5	176.18 (17)
C1—C2—C3—C4	0.1 (3)	C2—C1—C6—C5	0.1 (3)
Cl1—C2—C3—C4	179.96 (15)	O1—C1—C6—Cl3	−4.0 (3)
C2—C3—C4—C5	−0.2 (3)	C2—C1—C6—Cl3	179.92 (14)
C2—C3—C4—Cl2	179.51 (15)	C2—C1—O1—C7	−86.2 (2)
C3—C4—C5—C6	0.1 (3)	C6—C1—O1—C7	97.9 (2)