(Z)-2,3-Di-chloro-1,4-bis-(4-chloro-phen-yl)but-2-ene-1,4-dione.

The title compound, C16H8Cl4O2, crystallizes with two independent mol-ecules in the asymmetric unit. Both mol-ecules have a Z conformation around the central double bond and they show significantly different C-C-C-O torsion angles between the aromatic ring and the carbonyl group [30.1 (7) and 3.9 (7)° in one molecule and 23.5 (7) and 9.3 (8)° in the other]. The crystal packing shows short halogen Cl⋯O [3.003 (5) and 3.246 (4) Å] and Cl⋯Cl [3.452 (2) Å] contacts and aromatic C-H⋯Cl and C-H⋯O inter-actions link the molecules, resulting in chains propogating along [100]. The crystal structure also features π-π stacking inter-actions between aromatic units of the two independent mol-ecules, with a centroid-centroid distance of 3.9264 (6) Å.

Related literature

For general background and details of the synthesis, see: Clark (2002 ▶); Martin et al. (1985 ▶); Matyjaszewski & Xia (2001 ▶); Ram & Charles (1999 ▶); Ram & Kumar (2008 ▶); Ram & Tittal (2014a ▶,b ▶); Ram & Manoj (2008 ▶); Ram & Meher (2003 ▶); Ram et al. (2007 ▶); Tomislav & Matyjaszewski (2008 ▶). For halogen-bond inter­actions, see: Agarwal et al. (2014 ▶); Gonnade et al. (2008 ▶); Pedireddi et al. (1992 ▶). For short aromatic inteactions, see: Warad et al. (2013 ▶).

Experimental

Crystal data

C16H8Cl4O2

M = 374.02

Orthorhombic,

a = 19.065 (2) Å

b = 28.668 (4) Å

c = 11.8800 (14) Å

V = 6493.1 (14) Å3

Z = 16

Mo Kα radiation

μ = 0.73 mm−1

T = 273 K

0.37 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.782, T max = 0.863

31827 measured reflections

6044 independent reflections

5194 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.145

S = 1.13

6044 reflections

397 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1939 Friedel pairs

Absolute structure parameter: 0.08 (7)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶), PLATON (Spek, 2009 ▶) and SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814015463/fj2678sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015463/fj2678Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015463/fj2678Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015463/fj2678Isup4.cml

CCDC reference: 1011687

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H8Cl4O2	Dx = 1.530 Mg m−3
Mr = 374.02	Melting point: 383 K
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 5754 reflections
a = 19.065 (2) Å	θ = 3.2–26.1°
b = 28.668 (4) Å	µ = 0.73 mm−1
c = 11.8800 (14) Å	T = 273 K
V = 6493.1 (14) Å3	Block, colourless
Z = 16	0.37 × 0.28 × 0.20 mm
F(000) = 3008

Bruker SMART APEX CCD detector diffractometer	6044 independent reflections
Radiation source: fine-focus sealed tube	5194 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
φ and ω scans	θmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −23→23
Tmin = 0.782, Tmax = 0.863	k = −34→34
31827 measured reflections	l = −14→14

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0741P)2] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
6044 reflections	Δρmax = 0.31 e Å−3
397 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 1939 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (7)

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
C1	0.1802 (2)	0.18216 (14)	0.0202 (4)	0.0441 (10)
C2	0.2138 (3)	0.18813 (16)	−0.0820 (4)	0.0560 (12)
H2	0.2257	0.2180	−0.1056	0.067*
C3	0.2296 (2)	0.15075 (16)	−0.1490 (4)	0.0553 (12)
H3	0.2540	0.1549	−0.2160	0.066*
C4	0.2091 (2)	0.10726 (15)	−0.1158 (4)	0.0479 (11)
C5	0.1760 (2)	0.09998 (15)	−0.0130 (4)	0.0491 (11)
H5	0.1631	0.0701	0.0094	0.059*
C6	0.1627 (2)	0.13761 (17)	0.0547 (4)	0.0493 (11)
H6	0.1418	0.1332	0.1246	0.059*
C7	0.1635 (2)	0.22072 (15)	0.0995 (4)	0.0458 (10)
C8	0.1486 (3)	0.26865 (17)	0.0565 (4)	0.0520 (12)
C9	0.1600 (3)	0.30479 (17)	0.1200 (5)	0.0584 (13)
C10	0.1935 (3)	0.30333 (16)	0.2379 (5)	0.0543 (12)
C11	0.1455 (2)	0.30832 (14)	0.3351 (4)	0.0471 (11)
C12	0.1746 (3)	0.31256 (18)	0.4422 (5)	0.0612 (14)
H12	0.2231	0.3141	0.4499	0.073*
C13	0.1333 (3)	0.3145 (2)	0.5364 (5)	0.0653 (15)
H13	0.1531	0.3172	0.6077	0.078*
C14	0.0618 (3)	0.31252 (17)	0.5223 (4)	0.0595 (14)
C15	0.0316 (3)	0.30947 (19)	0.4183 (5)	0.0645 (14)
H15	−0.0169	0.3092	0.4113	0.077*
C16	0.0730 (3)	0.30681 (17)	0.3243 (5)	0.0586 (13)
H16	0.0526	0.3040	0.2535	0.070*
C17	0.1304 (3)	0.45602 (16)	0.5455 (4)	0.0494 (11)
C18	0.1596 (3)	0.4566 (2)	0.4390 (5)	0.0661 (15)
H18	0.2072	0.4631	0.4313	0.079*
C19	0.1208 (3)	0.4480 (2)	0.3454 (5)	0.0743 (16)
H19	0.1416	0.4484	0.2746	0.089*
C20	0.0506 (3)	0.43870 (19)	0.3565 (5)	0.0653 (14)
C21	0.0195 (3)	0.43733 (19)	0.4611 (5)	0.0681 (15)
H21	−0.0280	0.4306	0.4682	0.082*
C22	0.0595 (3)	0.44599 (18)	0.5550 (5)	0.0604 (13)
H22	0.0388	0.4451	0.6259	0.072*
C23	0.1738 (3)	0.46744 (16)	0.6438 (4)	0.0543 (12)
C24	0.1466 (3)	0.45532 (16)	0.7593 (4)	0.0552 (12)
C25	0.1170 (2)	0.48387 (16)	0.8325 (4)	0.0514 (12)
C26	0.1019 (2)	0.53398 (15)	0.8002 (4)	0.0462 (10)
C27	0.0991 (2)	0.57237 (16)	0.8868 (4)	0.0459 (11)
C28	0.1346 (2)	0.57170 (15)	0.9873 (4)	0.0466 (11)
H28	0.1594	0.5451	1.0085	0.056*
C29	0.1339 (3)	0.60992 (17)	1.0567 (4)	0.0584 (13)
H29	0.1595	0.6097	1.1234	0.070*
C30	0.0961 (3)	0.64784 (18)	1.0281 (5)	0.0671 (15)
C31	0.0593 (3)	0.64972 (18)	0.9285 (6)	0.0768 (17)
H31	0.0335	0.6761	0.9097	0.092*
C32	0.0614 (3)	0.61211 (17)	0.8578 (4)	0.0597 (13)
H32	0.0373	0.6131	0.7897	0.072*
Cl1	0.09338 (14)	0.69524 (6)	1.11846 (19)	0.1247 (8)
Cl2	0.08763 (8)	0.46534 (4)	0.96328 (11)	0.0696 (4)
Cl3	0.16115 (10)	0.39746 (4)	0.79049 (14)	0.0897 (5)
Cl4	−0.00090 (11)	0.42888 (7)	0.23804 (16)	0.1048 (6)
Cl5	0.00905 (9)	0.31287 (6)	0.64225 (14)	0.0877 (5)
Cl6	0.14301 (12)	0.36143 (5)	0.08012 (14)	0.0981 (6)
Cl7	0.11250 (8)	0.27538 (5)	−0.07659 (12)	0.0712 (4)
Cl8	0.22478 (7)	0.05907 (4)	−0.20286 (12)	0.0635 (3)
O1	0.1630 (2)	0.21511 (12)	0.1997 (3)	0.0657 (10)
O2	0.2555 (2)	0.30041 (15)	0.2467 (4)	0.0835 (12)
O3	0.0931 (2)	0.54208 (12)	0.7004 (3)	0.0653 (9)
O4	0.2329 (2)	0.48314 (14)	0.6368 (4)	0.0807 (12)

	U11	U22	U33	U12	U13	U23
C1	0.039 (2)	0.040 (2)	0.053 (3)	−0.0054 (18)	−0.001 (2)	0.005 (2)
C2	0.072 (3)	0.038 (2)	0.059 (3)	−0.005 (2)	0.006 (3)	0.009 (2)
C3	0.063 (3)	0.051 (3)	0.052 (3)	−0.005 (2)	0.010 (2)	0.005 (2)
C4	0.039 (2)	0.049 (3)	0.056 (3)	0.007 (2)	−0.009 (2)	−0.004 (2)
C5	0.048 (3)	0.039 (2)	0.061 (3)	−0.0011 (19)	0.002 (2)	0.007 (2)
C6	0.048 (3)	0.054 (3)	0.045 (3)	0.004 (2)	0.000 (2)	0.003 (2)
C7	0.050 (3)	0.043 (2)	0.044 (3)	0.003 (2)	−0.003 (2)	0.005 (2)
C8	0.065 (3)	0.044 (3)	0.047 (3)	0.011 (2)	0.003 (2)	0.004 (2)
C9	0.066 (3)	0.044 (3)	0.065 (3)	0.014 (2)	0.016 (3)	0.014 (2)
C10	0.062 (3)	0.037 (2)	0.063 (3)	−0.009 (2)	0.012 (3)	−0.004 (2)
C11	0.050 (3)	0.037 (2)	0.055 (3)	−0.0023 (19)	0.000 (2)	−0.006 (2)
C12	0.047 (3)	0.068 (3)	0.069 (4)	0.000 (2)	−0.008 (3)	−0.016 (3)
C13	0.066 (4)	0.075 (4)	0.054 (3)	0.025 (3)	−0.012 (3)	−0.020 (3)
C14	0.070 (3)	0.052 (3)	0.056 (3)	0.018 (2)	0.005 (3)	−0.009 (2)
C15	0.051 (3)	0.082 (4)	0.061 (3)	0.002 (3)	0.004 (3)	−0.011 (3)
C16	0.056 (3)	0.067 (3)	0.053 (3)	0.004 (2)	−0.008 (2)	−0.008 (2)
C17	0.054 (3)	0.041 (3)	0.052 (3)	−0.002 (2)	−0.003 (2)	−0.012 (2)
C18	0.056 (3)	0.075 (4)	0.067 (4)	−0.015 (3)	0.005 (3)	−0.012 (3)
C19	0.087 (4)	0.085 (4)	0.051 (3)	−0.006 (3)	0.005 (3)	−0.010 (3)
C20	0.076 (4)	0.062 (3)	0.058 (3)	0.001 (3)	−0.008 (3)	−0.011 (3)
C21	0.053 (3)	0.069 (3)	0.082 (4)	−0.012 (3)	−0.001 (3)	−0.010 (3)
C22	0.065 (3)	0.064 (3)	0.053 (3)	−0.009 (3)	0.006 (3)	0.004 (3)
C23	0.063 (3)	0.043 (3)	0.058 (3)	0.004 (2)	−0.001 (3)	−0.008 (2)
C24	0.071 (3)	0.039 (3)	0.055 (3)	0.004 (2)	−0.012 (2)	−0.009 (2)
C25	0.060 (3)	0.048 (3)	0.047 (3)	−0.004 (2)	−0.007 (2)	0.012 (2)
C26	0.043 (2)	0.048 (3)	0.047 (3)	−0.0041 (19)	−0.009 (2)	0.009 (2)
C27	0.051 (3)	0.049 (3)	0.038 (2)	0.006 (2)	0.009 (2)	0.005 (2)
C28	0.053 (3)	0.045 (2)	0.041 (2)	0.009 (2)	0.001 (2)	0.006 (2)
C29	0.079 (3)	0.053 (3)	0.043 (3)	0.003 (3)	−0.003 (3)	−0.002 (2)
C30	0.099 (4)	0.046 (3)	0.057 (3)	0.014 (3)	0.024 (3)	0.001 (2)
C31	0.096 (4)	0.048 (3)	0.086 (4)	0.036 (3)	0.004 (3)	0.006 (3)
C32	0.064 (3)	0.051 (3)	0.064 (3)	0.016 (2)	−0.008 (2)	0.004 (3)
Cl1	0.204 (2)	0.0658 (10)	0.1046 (15)	0.0227 (12)	0.0211 (15)	−0.0310 (10)
Cl2	0.1076 (11)	0.0476 (6)	0.0537 (8)	−0.0028 (7)	0.0051 (7)	0.0125 (6)
Cl3	0.1506 (14)	0.0439 (7)	0.0746 (10)	0.0210 (8)	−0.0108 (11)	−0.0020 (7)
Cl4	0.1133 (14)	0.1214 (15)	0.0795 (11)	−0.0006 (11)	−0.0345 (10)	−0.0287 (10)
Cl5	0.0900 (10)	0.1093 (13)	0.0638 (9)	0.0236 (9)	0.0217 (8)	−0.0129 (9)
Cl6	0.1784 (18)	0.0426 (7)	0.0734 (10)	0.0264 (9)	0.0176 (11)	0.0112 (7)
Cl7	0.0909 (10)	0.0691 (8)	0.0534 (7)	0.0193 (7)	−0.0084 (7)	0.0110 (6)
Cl8	0.0727 (8)	0.0537 (7)	0.0641 (8)	0.0115 (6)	−0.0026 (7)	−0.0138 (6)
O1	0.101 (3)	0.052 (2)	0.044 (2)	0.0158 (18)	0.0010 (19)	0.0062 (16)
O2	0.056 (2)	0.114 (3)	0.080 (3)	−0.010 (2)	0.011 (2)	−0.006 (2)
O3	0.095 (3)	0.055 (2)	0.046 (2)	0.0059 (18)	−0.0172 (19)	0.0064 (16)
O4	0.063 (2)	0.097 (3)	0.082 (3)	−0.016 (2)	−0.002 (2)	−0.028 (2)

C1—C6	1.382 (6)	C17—C18	1.382 (7)
C1—C2	1.383 (7)	C17—C22	1.386 (7)
C1—C7	1.487 (6)	C17—C23	1.468 (7)
C2—C3	1.368 (7)	C18—C19	1.359 (8)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.365 (6)	C19—C20	1.372 (8)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.390 (7)	C20—C21	1.377 (8)
C4—Cl8	1.751 (5)	C20—Cl4	1.738 (6)
C5—C6	1.369 (7)	C21—C22	1.374 (8)
C5—H5	0.9300	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—O1	1.201 (5)	C23—O4	1.216 (6)
C7—C8	1.493 (6)	C23—C24	1.508 (7)
C8—C9	1.299 (7)	C24—C25	1.322 (7)
C8—Cl7	1.736 (5)	C24—Cl3	1.722 (5)
C9—C10	1.541 (8)	C25—C26	1.514 (6)
C9—Cl6	1.722 (5)	C25—Cl2	1.735 (5)
C10—O2	1.190 (6)	C26—O3	1.220 (6)
C10—C11	1.479 (7)	C26—C27	1.507 (7)
C11—C16	1.389 (7)	C27—C28	1.373 (7)
C11—C12	1.393 (7)	C27—C32	1.390 (6)
C12—C13	1.369 (8)	C28—C29	1.371 (7)
C12—H12	0.9300	C28—H28	0.9300
C13—C14	1.375 (7)	C29—C30	1.348 (7)
C13—H13	0.9300	C29—H29	0.9300
C14—C15	1.366 (8)	C30—C31	1.377 (9)
C14—Cl5	1.744 (6)	C30—Cl1	1.733 (6)
C15—C16	1.369 (8)	C31—C32	1.367 (8)
C15—H15	0.9300	C31—H31	0.9300
C16—H16	0.9300	C32—H32	0.9300
C6—C1—C2	119.1 (4)	C18—C17—C22	118.0 (5)
C6—C1—C7	116.6 (4)	C18—C17—C23	119.9 (5)
C2—C1—C7	124.3 (4)	C22—C17—C23	122.1 (5)
C3—C2—C1	121.0 (4)	C19—C18—C17	121.9 (5)
C3—C2—H2	119.5	C19—C18—H18	119.1
C1—C2—H2	119.5	C17—C18—H18	119.1
C4—C3—C2	119.0 (5)	C18—C19—C20	119.2 (6)
C4—C3—H3	120.5	C18—C19—H19	120.4
C2—C3—H3	120.5	C20—C19—H19	120.4
C3—C4—C5	121.4 (4)	C19—C20—C21	120.8 (5)
C3—C4—Cl8	120.1 (4)	C19—C20—Cl4	120.3 (5)
C5—C4—Cl8	118.5 (4)	C21—C20—Cl4	118.9 (5)
C6—C5—C4	118.8 (4)	C22—C21—C20	119.3 (5)
C6—C5—H5	120.6	C22—C21—H21	120.4
C4—C5—H5	120.6	C20—C21—H21	120.4
C5—C6—C1	120.6 (4)	C21—C22—C17	120.8 (5)
C5—C6—H6	119.7	C21—C22—H22	119.6
C1—C6—H6	119.7	C17—C22—H22	119.6
O1—C7—C1	122.0 (4)	O4—C23—C17	123.4 (5)
O1—C7—C8	117.4 (4)	O4—C23—C24	117.8 (5)
C1—C7—C8	120.6 (4)	C17—C23—C24	118.6 (4)
C9—C8—C7	120.3 (4)	C25—C24—C23	127.1 (4)
C9—C8—Cl7	120.4 (4)	C25—C24—Cl3	121.6 (4)
C7—C8—Cl7	119.3 (4)	C23—C24—Cl3	111.3 (3)
C8—C9—C10	125.1 (4)	C24—C25—C26	120.1 (4)
C8—C9—Cl6	124.1 (4)	C24—C25—Cl2	122.5 (4)
C10—C9—Cl6	110.7 (4)	C26—C25—Cl2	117.1 (4)
O2—C10—C11	123.6 (5)	O3—C26—C27	121.3 (4)
O2—C10—C9	119.5 (5)	O3—C26—C25	116.9 (4)
C11—C10—C9	116.8 (4)	C27—C26—C25	121.8 (4)
C16—C11—C12	118.9 (5)	C28—C27—C32	118.8 (5)
C16—C11—C10	122.7 (5)	C28—C27—C26	124.4 (4)
C12—C11—C10	118.4 (4)	C32—C27—C26	116.6 (4)
C13—C12—C11	121.4 (5)	C29—C28—C27	120.4 (4)
C13—C12—H12	119.3	C29—C28—H28	119.8
C11—C12—H12	119.3	C27—C28—H28	119.8
C12—C13—C14	118.0 (5)	C30—C29—C28	119.9 (5)
C12—C13—H13	121.0	C30—C29—H29	120.1
C14—C13—H13	121.0	C28—C29—H29	120.1
C15—C14—C13	122.0 (5)	C29—C30—C31	121.4 (5)
C15—C14—Cl5	119.8 (4)	C29—C30—Cl1	119.5 (5)
C13—C14—Cl5	118.2 (4)	C31—C30—Cl1	119.1 (4)
C14—C15—C16	119.9 (5)	C32—C31—C30	118.8 (5)
C14—C15—H15	120.0	C32—C31—H31	120.6
C16—C15—H15	120.0	C30—C31—H31	120.6
C15—C16—C11	119.8 (5)	C31—C32—C27	120.6 (5)
C15—C16—H16	120.1	C31—C32—H32	119.7
C11—C16—H16	120.1	C27—C32—H32	119.7
C6—C1—C2—C3	0.1 (7)	C22—C17—C18—C19	0.4 (9)
C7—C1—C2—C3	177.8 (4)	C23—C17—C18—C19	−177.5 (5)
C1—C2—C3—C4	2.8 (8)	C17—C18—C19—C20	0.4 (9)
C2—C3—C4—C5	−3.6 (7)	C18—C19—C20—C21	−1.0 (9)
C2—C3—C4—Cl8	176.9 (4)	C18—C19—C20—Cl4	178.5 (5)
C3—C4—C5—C6	1.3 (7)	C19—C20—C21—C22	0.8 (9)
Cl8—C4—C5—C6	−179.2 (3)	Cl4—C20—C21—C22	−178.7 (4)
C4—C5—C6—C1	1.7 (7)	C20—C21—C22—C17	0.0 (8)
C2—C1—C6—C5	−2.4 (7)	C18—C17—C22—C21	−0.6 (8)
C7—C1—C6—C5	179.8 (4)	C23—C17—C22—C21	177.3 (5)
C6—C1—C7—O1	30.1 (7)	C18—C17—C23—O4	9.3 (8)
C2—C1—C7—O1	−147.6 (5)	C22—C17—C23—O4	−168.5 (5)
C6—C1—C7—C8	−151.7 (4)	C18—C17—C23—C24	−165.2 (5)
C2—C1—C7—C8	30.5 (7)	C22—C17—C23—C24	17.0 (7)
O1—C7—C8—C9	24.3 (7)	O4—C23—C24—C25	84.3 (7)
C1—C7—C8—C9	−153.9 (5)	C17—C23—C24—C25	−100.9 (6)
O1—C7—C8—Cl7	−153.0 (4)	O4—C23—C24—Cl3	−93.7 (5)
C1—C7—C8—Cl7	28.8 (6)	C17—C23—C24—Cl3	81.1 (5)
C7—C8—C9—C10	4.4 (8)	C23—C24—C25—C26	5.1 (8)
Cl7—C8—C9—C10	−178.3 (4)	Cl3—C24—C25—C26	−177.1 (3)
C7—C8—C9—Cl6	−178.6 (4)	C23—C24—C25—Cl2	179.9 (4)
Cl7—C8—C9—Cl6	−1.3 (7)	Cl3—C24—C25—Cl2	−2.3 (6)
C8—C9—C10—O2	80.1 (7)	C24—C25—C26—O3	26.5 (7)
Cl6—C9—C10—O2	−97.3 (5)	Cl2—C25—C26—O3	−148.6 (4)
C8—C9—C10—C11	−103.2 (6)	C24—C25—C26—C27	−152.6 (5)
Cl6—C9—C10—C11	79.5 (5)	Cl2—C25—C26—C27	32.3 (5)
O2—C10—C11—C16	−173.1 (5)	O3—C26—C27—C28	−152.0 (5)
C9—C10—C11—C16	10.3 (6)	C25—C26—C27—C28	27.0 (7)
O2—C10—C11—C12	3.9 (7)	O3—C26—C27—C32	23.5 (7)
C9—C10—C11—C12	−172.7 (4)	C25—C26—C27—C32	−157.5 (4)
C16—C11—C12—C13	1.0 (7)	C32—C27—C28—C29	−1.2 (7)
C10—C11—C12—C13	−176.1 (5)	C26—C27—C28—C29	174.2 (4)
C11—C12—C13—C14	−0.4 (8)	C27—C28—C29—C30	2.3 (8)
C12—C13—C14—C15	−1.2 (8)	C28—C29—C30—C31	−1.7 (9)
C12—C13—C14—Cl5	177.7 (4)	C28—C29—C30—Cl1	178.0 (4)
C13—C14—C15—C16	2.2 (9)	C29—C30—C31—C32	0.1 (9)
Cl5—C14—C15—C16	−176.7 (4)	Cl1—C30—C31—C32	−179.6 (5)
C14—C15—C16—C11	−1.5 (8)	C30—C31—C32—C27	1.0 (9)
C12—C11—C16—C15	0.0 (7)	C28—C27—C32—C31	−0.5 (8)
C10—C11—C16—C15	177.0 (5)	C26—C27—C32—C31	−176.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl7	0.93	2.74	3.160 (5)	109
C28—H28···Cl2	0.93	2.72	3.191 (5)	112
C3—H3···O1i	0.93	2.55	3.290 (6)	137
C5—H5···O3ii	0.93	2.75	3.418 (6)	129
C6—H6···O3ii	0.93	2.91	3.502 (6)	122
C13—H13···O2iii	0.93	2.45	3.302 (7)	152
C29—H29···Cl8iv	0.93	2.81	3.645 (5)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl7	0.93	2.74	3.160 (5)	109
C28—H28⋯Cl2	0.93	2.72	3.191 (5)	112
C3—H3⋯O1i	0.93	2.55	3.290 (6)	137
C5—H5⋯O3ii	0.93	2.75	3.418 (6)	129
C6—H6⋯O3ii	0.93	2.91	3.502 (6)	122
C13—H13⋯O2iii	0.93	2.45	3.302 (7)	152
C29—H29⋯Cl8iv	0.93	2.81	3.645 (5)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .