2,3,5-Trichloro-4-meth­oxy-6-[2,3,5-trichloro-4-meth­oxy-6-(2,3,5,6-tetra­chloro-4-methoxy­phen­oxy)phen­oxy]phenol

Hashizume, D.; Koshino, H.; Lee, I.-K.; Yoo, I.-D.

doi:10.1107/S1600536805011220

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2,3,5-Trichloro-4-methoxy-6-[2,3,5-trichloro-4-methoxy-6-(2,3,5,6-tetrachloro-4-methoxyphenoxy)phenoxy]phenol

D. Hashizume, H. Koshino, I.-K. Lee and I.-D. Yoo

The title compound, C₂₁H₁₀Cl₁₀O₆, has been extracted from mushroom Phellinus sp. The molecule has a highly chlorinated diarylcatechol ether skeleton. The neighboring benzene rings are arranged approximately perpendicular to each other. There are intermolecular O—H

O hydrogen bonds and Cl

Cl/O short contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011220/ob6499sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011220/ob6499Isup2.hkl Contains datablock I

CCDC reference: 272055

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.034
wR factor = 0.078
Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  Cl2     ..       3.40 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  Cl6     ..       3.40 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  O5      ..       3.25 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl8    ..  O2      ..       3.19 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl9    ..  Cl9     ..       3.34 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: R-AXIS Control Software (Rigaku, 1996); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

2,3,5-Trichloro-4-methoxy-6-[2,3,5-trichloro-4-methoxy-6- (2,3,5,6-tetrachloro-4-methoxyphenoxy)phenoxy]phenol top

Crystal data top

C₂₁H₁₀Cl₁₀O₆	F(000) = 1416
M_r = 712.79	D_x = 1.775 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 54841 reflections
a = 7.5031 (13) Å	θ = 3.1–27.6°
b = 19.610 (3) Å	µ = 1.08 mm⁻¹
c = 18.401 (4) Å	T = 100 K
β = 99.894 (7)°	Block, pale yellow
V = 2667.2 (8) Å³	0.43 × 0.35 × 0.25 mm
Z = 4

Data collection top

Rigaku R-AXIS diffractometer	6109 independent reflections
Radiation source: fine-focus rotaing anode	5306 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
Oscillation scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −25→25
T_min = 0.712, T_max = 0.782	l = −23→23
60732 measured reflections

Refinement top

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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.078	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.026P)² + 1.942P] where P = (F_o² + 2F_c²)/3
6109 reflections	(Δ/σ)_max = 0.001
338 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.01224 (7)	0.44964 (3)	0.07948 (3)	0.02241 (12)
Cl2	0.41230 (7)	0.50159 (3)	0.07917 (3)	0.02075 (12)
Cl3	0.66371 (7)	0.30710 (3)	0.27674 (3)	0.02440 (13)
O1	−0.00402 (19)	0.32827 (8)	0.17799 (10)	0.0231 (4)
H1	−0.0829	0.3579	0.1634	0.028*
O2	0.6918 (2)	0.42348 (8)	0.17705 (9)	0.0201 (3)
C1	0.1635 (3)	0.35448 (11)	0.17629 (12)	0.0161 (4)
C2	0.1959 (3)	0.41073 (11)	0.13351 (12)	0.0158 (4)
C3	0.3717 (3)	0.43449 (10)	0.13476 (12)	0.0167 (4)
C4	0.5164 (3)	0.40292 (11)	0.17884 (12)	0.0166 (4)
C5	0.4855 (3)	0.34661 (11)	0.22124 (12)	0.0162 (4)
C6	0.3109 (3)	0.32184 (11)	0.21891 (11)	0.0151 (4)
C7	0.7537 (3)	0.47431 (15)	0.23065 (15)	0.0326 (6)
H71	0.8793	0.4862	0.2280	0.049*
H72	0.7469	0.4568	0.2800	0.049*
H73	0.6775	0.5150	0.2209	0.049*
Cl4	0.32006 (8)	0.19051 (3)	0.12703 (3)	0.02434 (12)
Cl5	0.05529 (9)	0.06335 (3)	0.10191 (3)	0.02945 (14)
Cl6	−0.21356 (8)	0.13306 (3)	0.34475 (3)	0.02365 (12)
O3	0.29327 (19)	0.26825 (8)	0.26586 (8)	0.0168 (3)
O4	−0.1721 (2)	0.04803 (8)	0.21579 (9)	0.0246 (4)
C8	0.1692 (3)	0.21661 (11)	0.24692 (12)	0.0154 (4)
C9	0.1692 (3)	0.17413 (11)	0.18626 (12)	0.0179 (4)
C10	0.0508 (3)	0.11891 (11)	0.17466 (12)	0.0189 (4)
C11	−0.0690 (3)	0.10598 (11)	0.22333 (12)	0.0185 (4)
C12	−0.0692 (3)	0.14931 (11)	0.28360 (12)	0.0166 (4)
C13	0.0523 (3)	0.20335 (10)	0.29638 (11)	0.0146 (4)
C14	−0.3539 (3)	0.05798 (14)	0.17684 (15)	0.0311 (6)
H141	−0.4172	0.0141	0.1713	0.047*
H142	−0.3500	0.0773	0.1280	0.047*
H143	−0.4182	0.0894	0.2048	0.047*
Cl7	0.24153 (8)	0.12327 (3)	0.43189 (3)	0.02112 (12)
Cl8	0.62332 (7)	0.15684 (3)	0.52390 (3)	0.02116 (12)
Cl9	0.51988 (9)	0.42292 (3)	0.46342 (3)	0.02783 (13)
Cl10	0.13882 (8)	0.39017 (3)	0.36732 (3)	0.02297 (12)
O5	0.0492 (2)	0.24493 (7)	0.35727 (8)	0.0153 (3)
O6	0.7128 (2)	0.30309 (8)	0.53128 (8)	0.0208 (3)
C15	0.2146 (3)	0.25822 (10)	0.40158 (11)	0.0144 (4)
C16	0.3203 (3)	0.20594 (10)	0.43802 (11)	0.0156 (4)
C17	0.4885 (3)	0.22096 (11)	0.48020 (11)	0.0158 (4)
C18	0.5506 (3)	0.28820 (11)	0.48805 (11)	0.0162 (4)
C19	0.4404 (3)	0.34023 (11)	0.45385 (12)	0.0173 (4)
C20	0.2725 (3)	0.32587 (10)	0.41113 (12)	0.0162 (4)
C21	0.8649 (3)	0.29342 (15)	0.49355 (15)	0.0317 (6)
H211	0.9778	0.2961	0.5293	0.048*
H212	0.8640	0.3290	0.4561	0.048*
H213	0.8560	0.2486	0.4697	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0176 (2)	0.0232 (3)	0.0264 (3)	0.0025 (2)	0.0037 (2)	0.0111 (2)
Cl2	0.0264 (3)	0.0131 (2)	0.0260 (3)	−0.0016 (2)	0.0135 (2)	0.0037 (2)
Cl3	0.0132 (2)	0.0320 (3)	0.0267 (3)	0.0020 (2)	0.0000 (2)	0.0084 (2)
O1	0.0076 (7)	0.0242 (8)	0.0371 (10)	−0.0012 (6)	0.0024 (6)	0.0173 (7)
O2	0.0144 (7)	0.0208 (8)	0.0265 (8)	−0.0060 (6)	0.0077 (6)	−0.0039 (7)
C1	0.0157 (10)	0.0173 (10)	0.0160 (10)	−0.0029 (8)	0.0049 (8)	0.0025 (8)
C2	0.0165 (10)	0.0144 (9)	0.0168 (10)	0.0014 (8)	0.0040 (8)	0.0020 (8)
C3	0.0223 (11)	0.0115 (9)	0.0190 (10)	−0.0022 (8)	0.0110 (9)	0.0005 (8)
C4	0.0144 (10)	0.0168 (10)	0.0200 (10)	−0.0038 (8)	0.0073 (8)	−0.0032 (8)
C5	0.0126 (9)	0.0188 (10)	0.0179 (10)	0.0012 (8)	0.0043 (8)	−0.0001 (8)
C6	0.0155 (10)	0.0167 (10)	0.0142 (10)	−0.0017 (8)	0.0059 (8)	0.0031 (8)
C7	0.0175 (11)	0.0449 (16)	0.0349 (14)	−0.0098 (11)	0.0032 (10)	−0.0174 (12)
Cl4	0.0269 (3)	0.0297 (3)	0.0193 (3)	0.0040 (2)	0.0123 (2)	0.0034 (2)
Cl5	0.0462 (4)	0.0206 (3)	0.0212 (3)	0.0042 (3)	0.0050 (3)	−0.0036 (2)
Cl6	0.0229 (3)	0.0247 (3)	0.0254 (3)	−0.0078 (2)	0.0099 (2)	0.0043 (2)
O3	0.0164 (7)	0.0190 (7)	0.0147 (7)	−0.0042 (6)	0.0019 (6)	0.0064 (6)
O4	0.0262 (9)	0.0147 (7)	0.0308 (9)	−0.0028 (7)	−0.0017 (7)	0.0016 (7)
C8	0.0144 (9)	0.0150 (9)	0.0165 (10)	0.0004 (8)	0.0018 (8)	0.0064 (8)
C9	0.0213 (11)	0.0187 (10)	0.0146 (10)	0.0056 (9)	0.0057 (8)	0.0072 (8)
C10	0.0260 (11)	0.0150 (10)	0.0148 (10)	0.0046 (9)	0.0010 (9)	0.0011 (8)
C11	0.0206 (11)	0.0126 (9)	0.0209 (11)	0.0001 (8)	−0.0003 (9)	0.0040 (8)
C12	0.0173 (10)	0.0153 (10)	0.0180 (10)	0.0008 (8)	0.0049 (8)	0.0060 (8)
C13	0.0172 (10)	0.0139 (9)	0.0128 (9)	0.0020 (8)	0.0025 (8)	0.0029 (8)
C14	0.0242 (12)	0.0318 (14)	0.0344 (14)	−0.0026 (11)	−0.0032 (11)	−0.0023 (11)
Cl7	0.0258 (3)	0.0115 (2)	0.0250 (3)	−0.0016 (2)	0.0013 (2)	0.0054 (2)
Cl8	0.0238 (3)	0.0183 (2)	0.0202 (3)	0.0055 (2)	0.0005 (2)	0.0044 (2)
Cl9	0.0376 (3)	0.0132 (2)	0.0296 (3)	−0.0055 (2)	−0.0028 (3)	−0.0016 (2)
Cl10	0.0273 (3)	0.0132 (2)	0.0272 (3)	0.0044 (2)	0.0012 (2)	0.0044 (2)
O5	0.0158 (7)	0.0149 (7)	0.0159 (7)	0.0002 (6)	0.0042 (6)	−0.0001 (6)
O6	0.0215 (8)	0.0243 (8)	0.0160 (7)	−0.0011 (7)	0.0018 (6)	−0.0055 (6)
C15	0.0171 (10)	0.0141 (10)	0.0134 (10)	−0.0004 (8)	0.0069 (8)	0.0016 (8)
C16	0.0209 (10)	0.0117 (9)	0.0156 (10)	−0.0003 (8)	0.0071 (8)	0.0019 (8)
C17	0.0194 (10)	0.0152 (10)	0.0138 (10)	0.0051 (8)	0.0058 (8)	0.0029 (8)
C18	0.0193 (10)	0.0195 (10)	0.0104 (9)	0.0010 (8)	0.0048 (8)	−0.0011 (8)
C19	0.0236 (11)	0.0130 (9)	0.0159 (10)	−0.0021 (8)	0.0053 (8)	−0.0017 (8)
C20	0.0217 (10)	0.0113 (9)	0.0164 (10)	0.0037 (8)	0.0059 (8)	0.0023 (8)
C21	0.0231 (12)	0.0411 (15)	0.0323 (14)	−0.0062 (11)	0.0083 (10)	−0.0127 (12)

Geometric parameters (Å, º) top

Cl1—C2	1.732 (2)	C9—C10	1.394 (3)
Cl2—C3	1.726 (2)	C10—C11	1.397 (3)
Cl3—C5	1.721 (2)	C11—C12	1.397 (3)
O1—C1	1.364 (2)	C12—C13	1.391 (3)
O1—H1	0.8400	C13—O5	1.389 (2)
O2—C4	1.382 (2)	C14—H141	0.9800
O2—C7	1.423 (3)	C14—H142	0.9800
C1—C6	1.396 (3)	C14—H143	0.9800
C1—C2	1.400 (3)	Cl7—C16	1.723 (2)
C2—C3	1.396 (3)	Cl8—C17	1.724 (2)
C3—C4	1.385 (3)	Cl9—C19	1.726 (2)
C4—C5	1.394 (3)	Cl10—C20	1.723 (2)
C5—C6	1.391 (3)	O5—C15	1.388 (3)
C6—O3	1.381 (2)	O6—C18	1.366 (3)
C7—H71	0.9800	O6—C21	1.447 (3)
C7—H72	0.9800	C15—C16	1.396 (3)
C7—H73	0.9800	C15—C20	1.398 (3)
Cl4—C9	1.731 (2)	C16—C17	1.394 (3)
Cl5—C10	1.731 (2)	C17—C18	1.398 (3)
Cl6—C12	1.720 (2)	C18—C19	1.393 (3)
O3—C8	1.379 (2)	C19—C20	1.395 (3)
O4—C11	1.368 (3)	C21—H211	0.9800
O4—C14	1.441 (3)	C21—H212	0.9800
C8—C9	1.393 (3)	C21—H213	0.9800
C8—C13	1.393 (3)

Cl2···Cl6ⁱ	3.3982 (8)	Cl9···Cl9^iv	3.3432 (12)
Cl6···Cl2ⁱⁱ	3.3982 (8)	Cl3···O5^v	3.2518 (16)
Cl2···Cl2ⁱⁱⁱ	3.3973 (12)	Cl8···O2^vi	3.1922 (17)

C1—O1—H1	109.5	C10—C11—C12	119.2 (2)
C4—O2—C7	112.74 (17)	C13—C12—C11	120.5 (2)
O1—C1—C6	117.30 (18)	C13—C12—Cl6	119.90 (17)
O1—C1—C2	124.00 (19)	C11—C12—Cl6	119.55 (17)
C6—C1—C2	118.68 (19)	O5—C13—C12	118.81 (18)
C3—C2—C1	120.6 (2)	O5—C13—C8	121.15 (19)
C3—C2—Cl1	121.26 (16)	C12—C13—C8	120.0 (2)
C1—C2—Cl1	118.19 (16)	O4—C14—H141	109.5
C4—C3—C2	120.29 (19)	O4—C14—H142	109.5
C4—C3—Cl2	119.17 (16)	H141—C14—H142	109.5
C2—C3—Cl2	120.50 (17)	O4—C14—H143	109.5
O2—C4—C3	120.65 (19)	H141—C14—H143	109.5
O2—C4—C5	119.67 (19)	H142—C14—H143	109.5
C3—C4—C5	119.51 (19)	C15—O5—C13	116.53 (16)
C6—C5—C4	120.38 (19)	C18—O6—C21	112.96 (17)
C6—C5—Cl3	119.51 (17)	O5—C15—C16	121.44 (18)
C4—C5—Cl3	120.11 (16)	O5—C15—C20	118.66 (18)
O3—C6—C5	115.93 (18)	C16—C15—C20	119.9 (2)
O3—C6—C1	123.27 (18)	C17—C16—C15	119.84 (19)
C5—C6—C1	120.53 (19)	C17—C16—Cl7	120.19 (16)
O2—C7—H71	109.5	C15—C16—Cl7	119.96 (17)
O2—C7—H72	109.5	C16—C17—C18	120.69 (19)
H71—C7—H72	109.5	C16—C17—Cl8	120.52 (16)
O2—C7—H73	109.5	C18—C17—Cl8	118.79 (17)
H71—C7—H73	109.5	O6—C18—C19	120.4 (2)
H72—C7—H73	109.5	O6—C18—C17	120.63 (19)
C8—O3—C6	122.25 (16)	C19—C18—C17	118.9 (2)
C11—O4—C14	114.10 (18)	C18—C19—C20	121.01 (19)
O3—C8—C9	123.31 (19)	C18—C19—Cl9	118.31 (17)
O3—C8—C13	116.46 (19)	C20—C19—Cl9	120.66 (16)
C9—C8—C13	119.9 (2)	C19—C20—C15	119.59 (19)
C8—C9—C10	120.0 (2)	C19—C20—Cl10	120.87 (16)
C8—C9—Cl4	118.91 (17)	C15—C20—Cl10	119.51 (17)
C10—C9—Cl4	121.08 (17)	O6—C21—H211	109.5
C9—C10—C11	120.4 (2)	O6—C21—H212	109.5
C9—C10—Cl5	120.73 (17)	H211—C21—H212	109.5
C11—C10—Cl5	118.82 (17)	O6—C21—H213	109.5
O4—C11—C10	120.0 (2)	H211—C21—H213	109.5
O4—C11—C12	120.5 (2)	H212—C21—H213	109.5

O1—C1—C2—C3	−180.0 (2)	O4—C11—C12—C13	171.76 (19)
C6—C1—C2—C3	−1.4 (3)	C10—C11—C12—C13	−2.1 (3)
O1—C1—C2—Cl1	0.1 (3)	O4—C11—C12—Cl6	−5.1 (3)
C6—C1—C2—Cl1	178.71 (16)	C10—C11—C12—Cl6	−178.94 (16)
C1—C2—C3—C4	−0.4 (3)	C11—C12—C13—O5	−179.39 (19)
Cl1—C2—C3—C4	179.49 (16)	Cl6—C12—C13—O5	−2.5 (3)
C1—C2—C3—Cl2	177.32 (17)	C11—C12—C13—C8	3.2 (3)
Cl1—C2—C3—Cl2	−2.7 (3)	Cl6—C12—C13—C8	−179.97 (16)
C7—O2—C4—C3	91.8 (3)	O3—C8—C13—O5	6.6 (3)
C7—O2—C4—C5	−93.0 (3)	C9—C8—C13—O5	−179.86 (18)
C2—C3—C4—O2	176.06 (19)	O3—C8—C13—C12	−176.00 (18)
Cl2—C3—C4—O2	−1.7 (3)	C9—C8—C13—C12	−2.5 (3)
C2—C3—C4—C5	0.9 (3)	C12—C13—O5—C15	131.7 (2)
Cl2—C3—C4—C5	−176.94 (16)	C8—C13—O5—C15	−50.9 (3)
O2—C4—C5—C6	−174.69 (19)	C13—O5—C15—C16	−61.5 (2)
C3—C4—C5—C6	0.6 (3)	C13—O5—C15—C20	120.3 (2)
O2—C4—C5—Cl3	5.1 (3)	O5—C15—C16—C17	177.95 (18)
C3—C4—C5—Cl3	−179.60 (16)	C20—C15—C16—C17	−3.9 (3)
C4—C5—C6—O3	−176.62 (19)	O5—C15—C16—Cl7	−3.0 (3)
Cl3—C5—C6—O3	3.5 (3)	C20—C15—C16—Cl7	175.13 (16)
C4—C5—C6—C1	−2.4 (3)	C15—C16—C17—C18	1.7 (3)
Cl3—C5—C6—C1	177.76 (16)	Cl7—C16—C17—C18	−177.34 (16)
O1—C1—C6—O3	−4.8 (3)	C15—C16—C17—Cl8	−178.51 (16)
C2—C1—C6—O3	176.54 (19)	Cl7—C16—C17—Cl8	2.4 (2)
O1—C1—C6—C5	−178.5 (2)	C21—O6—C18—C19	−100.0 (2)
C2—C1—C6—C5	2.8 (3)	C21—O6—C18—C17	83.1 (3)
C5—C6—O3—C8	−144.9 (2)	C16—C17—C18—O6	177.92 (18)
C1—C6—O3—C8	41.1 (3)	Cl8—C17—C18—O6	−1.8 (3)
C6—O3—C8—C9	60.1 (3)	C16—C17—C18—C19	0.9 (3)
C6—O3—C8—C13	−126.6 (2)	Cl8—C17—C18—C19	−178.87 (15)
O3—C8—C9—C10	173.78 (19)	O6—C18—C19—C20	−178.35 (19)
C13—C8—C9—C10	0.7 (3)	C17—C18—C19—C20	−1.3 (3)
O3—C8—C9—Cl4	−5.3 (3)	O6—C18—C19—Cl9	3.5 (3)
C13—C8—C9—Cl4	−178.32 (16)	C17—C18—C19—Cl9	−179.44 (16)
C8—C9—C10—C11	0.4 (3)	C18—C19—C20—C15	−0.9 (3)
Cl4—C9—C10—C11	179.39 (17)	Cl9—C19—C20—C15	177.20 (17)
C8—C9—C10—Cl5	−177.16 (16)	C18—C19—C20—Cl10	−178.59 (16)
Cl4—C9—C10—Cl5	1.9 (3)	Cl9—C19—C20—Cl10	−0.5 (3)
C14—O4—C11—C10	−98.0 (2)	O5—C15—C20—C19	−178.32 (18)
C14—O4—C11—C12	88.2 (3)	C16—C15—C20—C19	3.5 (3)
C9—C10—C11—O4	−173.56 (19)	O5—C15—C20—Cl10	−0.6 (3)
Cl5—C10—C11—O4	4.0 (3)	C16—C15—C20—Cl10	−178.74 (16)
C9—C10—C11—C12	0.3 (3)	H1—O1—C1—C2	−20.78
Cl5—C10—C11—C12	177.88 (16)	H1—O1—C1—C6	160.60

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) x+1, y, z; (vi) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1	0.84	2.55	3.007 (2)	115
O1—H1···O2^vii	0.84	2.17	2.946 (2)	153

Symmetry code: (vii) x−1, y, z.

Geometry of intermolecular Cl···Cl contact (Å, °) top

C—Cl···Cl—C	Cl···Cl	C—Cl···Cl	Cl···Cl—C
C3—Cl2···Cl2^iv—C3^iv	3.3973 (12)	128.92 (8)	128.92 (8)
C19—Cl9···Cl9^v—C19^v	3.3432 (12)	146.86 (9)	146.86 (9)
C3—Cl2···Cl6^vi—C12^vi	3.3982 (8)	101.51 (7)	141.27 (8)

Symmetry codes: (iv) 1-x, 1-y, -z; (v) 1-x, 1-y, 1-z; (vi) -x, y+1/2, 1/2-z.

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