2a,8a-Dichloro-1-(2-ethynylphen­yl)-2a,8a-dihydro­cyclo­buta[b]naphthalene-3,8-dione

An, H.-Y.; Xu, J.-H.; Ng, S.-L.; Fun, H.-K.

doi:10.1107/S160053680700342X

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2a,8a-Dichloro-1-(2-ethynylphenyl)-2a,8a-dihydrocyclobuta[b]naphthalene-3,8-dione

H.-Y. An, J.-H. Xu, S.-L. Ng and H.-K. Fun

The title compound, C₂₀H₁₀Cl₂O₂, crystallizes with two crystallographically independent molecules in the asymmetric unit. In both molecules, the cyclohexene ring adopts a boat conformation. The molecules are linked into a sheet parallel to the ab plane by C—H

Cl hydrogen bonds and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700342X/ci2281sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680700342X/ci2281Isup2.hkl Contains datablock I

CCDC reference: 636217

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.086
Data-to-parameter ratio = 37.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C7A    -   C8A     ..       7.11 su
PLAT366_ALERT_2_B Short? C(sp?)-C(sp?) Bond  C19A   -   C20A   ...       1.20 Ang.

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.540
           From the CIF: _refine_ls_abs_structure_Flack_su    0.020
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.54
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.06
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT320_ALERT_2_C Check Hybridisation of  C20A   in Main Residue .          ?
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C14A   -   C19A   ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C14B   -   C19B   ...       1.44 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           37.50
           From the CIF: _reflns_number_total              16384
           Count of symmetry unique reflns         8349
           Completeness (_total/calc)            196.24%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      8035
           Fraction of Friedel pairs measured     0.962
           Are heavy atom types Z>Si present        yes
PLAT792_ALERT_1_G Check the Absolute Configuration of C1A    = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C1B    = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C10A   = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C10B   = ...          R

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2a,8a-Dichloro-1-(2-ethynylphenyl)-2a,8a-dihydrocyclobuta[b]naphthalene- 3,8-dione top

Crystal data top

C₂₀H₁₀Cl₂O₂	F(000) = 1440
M_r = 353.18	D_x = 1.507 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9833 reflections
a = 16.0627 (2) Å	θ = 2.5–37.5°
b = 8.0482 (1) Å	µ = 0.43 mm⁻¹
c = 24.0821 (3) Å	T = 100 K
V = 3113.23 (7) Å³	Block, orange
Z = 8	0.47 × 0.41 × 0.30 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	16384 independent reflections
Radiation source: fine-focus sealed tube	15176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 8.33 pixels mm^-1	θ_max = 37.5°, θ_min = 2.5°
ω scans	h = −27→27
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.822, T_max = 0.883	l = −41→41
127742 measured reflections

Refinement top

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0511P)² + 0.4718P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
16384 reflections	Δρ_max = 0.55 e Å⁻³
434 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 8036 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.54 (2)

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl1A	0.473786 (14)	0.40500 (3)	0.089027 (10)	0.01672 (4)
Cl2A	0.585614 (16)	0.08227 (3)	0.095918 (11)	0.01891 (5)
O1A	0.57237 (5)	0.67058 (10)	0.13291 (3)	0.01744 (13)
O2A	0.76456 (5)	0.15335 (9)	0.10348 (4)	0.01949 (14)
C1A	0.58036 (6)	0.43142 (11)	0.07289 (4)	0.01231 (14)
C2A	0.61648 (6)	0.57327 (11)	0.10748 (4)	0.01251 (14)
C3A	0.70816 (6)	0.58874 (10)	0.10692 (4)	0.01193 (13)
C4A	0.74310 (6)	0.74536 (11)	0.11503 (4)	0.01455 (15)
H4AA	0.7090	0.8379	0.1192	0.017*
C5A	0.82928 (7)	0.76281 (12)	0.11682 (4)	0.01653 (16)
H5AA	0.8528	0.8676	0.1212	0.020*
C6A	0.88034 (6)	0.62328 (13)	0.11207 (4)	0.01710 (16)
H6AA	0.9379	0.6350	0.1139	0.021*
C7A	0.84550 (6)	0.46661 (12)	0.10457 (4)	0.01638 (16)
H7AA	0.8798	0.3740	0.1016	0.020*
C8A	0.75932 (6)	0.44790 (11)	0.10144 (4)	0.01225 (13)
C9A	0.72343 (6)	0.27804 (11)	0.09548 (4)	0.01342 (14)
C10A	0.63474 (6)	0.26559 (11)	0.07191 (4)	0.01319 (14)
C11A	0.63711 (6)	0.28848 (12)	0.00978 (4)	0.01594 (16)
H11A	0.6707	0.2271	−0.0138	0.019*
C12A	0.59559 (6)	0.43469 (12)	0.01028 (4)	0.01380 (14)
C13A	0.57228 (6)	0.56193 (13)	−0.02984 (4)	0.01625 (16)
C14A	0.58093 (7)	0.53649 (14)	−0.08757 (4)	0.01779 (16)
C15A	0.56186 (8)	0.66640 (16)	−0.12426 (5)	0.0247 (2)
H15A	0.5676	0.6500	−0.1623	0.030*
C16A	0.53456 (10)	0.81897 (16)	−0.10457 (5)	0.0296 (2)
H16A	0.5222	0.9041	−0.1293	0.036*
C17A	0.52571 (10)	0.84445 (17)	−0.04775 (6)	0.0307 (3)
H17A	0.5080	0.9471	−0.0345	0.037*
C18A	0.54339 (8)	0.71601 (14)	−0.01067 (5)	0.0234 (2)
H18A	0.5359	0.7328	0.0272	0.028*
C19A	0.61027 (7)	0.38237 (15)	−0.10979 (4)	0.02106 (18)
C20A	0.63533 (9)	0.25598 (18)	−0.13042 (5)	0.0288 (2)
H20A	0.6678	0.1695	−0.1481	0.035*
Cl1B	0.251036 (14)	0.90536 (3)	0.252170 (10)	0.01558 (4)
Cl2B	0.138278 (16)	0.58520 (3)	0.247490 (12)	0.01898 (5)
O1B	0.15336 (5)	1.17567 (10)	0.21153 (4)	0.01857 (13)
O2B	−0.04078 (5)	0.65792 (9)	0.24103 (4)	0.02020 (14)
C1B	0.14500 (6)	0.93362 (11)	0.26998 (4)	0.01226 (14)
C2B	0.10914 (6)	1.07745 (11)	0.23605 (4)	0.01248 (14)
C3B	0.01730 (6)	1.09214 (10)	0.23564 (4)	0.01132 (13)
C4B	−0.01748 (6)	1.24941 (11)	0.22730 (4)	0.01385 (14)
H4BA	0.0168	1.3418	0.2233	0.017*
C5B	−0.10347 (7)	1.26699 (13)	0.22503 (4)	0.01637 (16)
H5BA	−0.1268	1.3718	0.2204	0.020*
C6B	−0.15490 (6)	1.12810 (13)	0.22962 (4)	0.01716 (16)
H6BA	−0.2124	1.1405	0.2275	0.021*
C7B	−0.12057 (6)	0.97100 (12)	0.23728 (4)	0.01477 (15)
H7BA	−0.1551	0.8786	0.2401	0.018*
C8B	−0.03416 (6)	0.95193 (11)	0.24078 (4)	0.01205 (13)
C9B	0.00084 (6)	0.78230 (11)	0.24803 (4)	0.01283 (13)
C10B	0.08953 (6)	0.76985 (11)	0.27118 (4)	0.01289 (14)
C11B	0.08879 (6)	0.79211 (13)	0.33348 (4)	0.01588 (15)
H11B	0.0597	0.7270	0.3637	0.019*
C12B	0.13224 (6)	0.93543 (12)	0.33297 (4)	0.01403 (14)
C13B	0.16193 (6)	1.05498 (14)	0.37398 (4)	0.01755 (16)
C14B	0.16783 (7)	1.01181 (16)	0.43092 (4)	0.02201 (19)
C15B	0.19649 (9)	1.1299 (2)	0.46918 (5)	0.0312 (3)
H15B	0.2009	1.1019	0.5065	0.037*
C16B	0.21834 (9)	1.2878 (2)	0.45177 (7)	0.0353 (3)
H16B	0.2369	1.3655	0.4775	0.042*
C17B	0.21270 (9)	1.33103 (18)	0.39600 (6)	0.0329 (3)
H17B	0.2270	1.4377	0.3846	0.039*
C18B	0.18565 (8)	1.21442 (15)	0.35728 (5)	0.0246 (2)
H18B	0.1833	1.2429	0.3199	0.030*
C19B	0.14780 (8)	0.84852 (18)	0.45091 (5)	0.0264 (2)
C20B	0.13319 (11)	0.7156 (2)	0.47028 (6)	0.0371 (3)
H20B	0.1152	0.6067	0.4851	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.01191 (8)	0.01648 (9)	0.02175 (10)	−0.00052 (6)	0.00153 (7)	−0.00119 (8)
Cl2A	0.01867 (10)	0.01132 (8)	0.02675 (12)	−0.00234 (7)	0.00003 (8)	0.00128 (8)
O1A	0.0165 (3)	0.0152 (3)	0.0207 (3)	0.0025 (2)	0.0030 (2)	−0.0044 (3)
O2A	0.0186 (3)	0.0117 (3)	0.0282 (4)	0.0044 (2)	−0.0029 (3)	0.0012 (3)
C1A	0.0115 (3)	0.0124 (3)	0.0130 (3)	0.0004 (3)	0.0011 (3)	−0.0001 (3)
C2A	0.0144 (4)	0.0108 (3)	0.0123 (3)	0.0012 (3)	0.0007 (3)	0.0004 (3)
C3A	0.0130 (3)	0.0102 (3)	0.0126 (3)	0.0004 (2)	0.0002 (3)	0.0006 (2)
C4A	0.0171 (4)	0.0106 (3)	0.0160 (4)	−0.0008 (3)	0.0000 (3)	0.0000 (3)
C5A	0.0171 (4)	0.0139 (3)	0.0186 (4)	−0.0042 (3)	0.0011 (3)	0.0011 (3)
C6A	0.0133 (4)	0.0186 (4)	0.0194 (4)	−0.0013 (3)	−0.0003 (3)	0.0002 (3)
C7A	0.0149 (4)	0.0155 (4)	0.0187 (4)	0.0017 (3)	0.0000 (3)	0.0006 (3)
C8A	0.0116 (3)	0.0114 (3)	0.0137 (3)	0.0006 (3)	0.0000 (3)	0.0002 (3)
C9A	0.0143 (3)	0.0110 (3)	0.0150 (3)	0.0010 (3)	−0.0005 (3)	0.0002 (3)
C10A	0.0137 (4)	0.0106 (3)	0.0153 (3)	0.0003 (3)	−0.0007 (3)	−0.0007 (3)
C11A	0.0183 (4)	0.0154 (4)	0.0141 (3)	0.0034 (3)	−0.0004 (3)	−0.0026 (3)
C12A	0.0149 (3)	0.0140 (3)	0.0126 (3)	0.0012 (3)	−0.0007 (3)	−0.0008 (3)
C13A	0.0175 (4)	0.0170 (4)	0.0143 (4)	0.0030 (3)	−0.0018 (3)	0.0006 (3)
C14A	0.0187 (4)	0.0205 (4)	0.0142 (3)	−0.0001 (3)	−0.0023 (3)	0.0004 (3)
C15A	0.0313 (6)	0.0267 (5)	0.0161 (4)	0.0002 (4)	−0.0050 (4)	0.0042 (4)
C16A	0.0405 (7)	0.0243 (5)	0.0241 (5)	0.0048 (5)	−0.0079 (5)	0.0074 (4)
C17A	0.0454 (8)	0.0215 (5)	0.0252 (5)	0.0123 (5)	−0.0050 (5)	0.0032 (4)
C18A	0.0332 (6)	0.0190 (4)	0.0182 (4)	0.0096 (4)	−0.0023 (4)	−0.0001 (3)
C19A	0.0244 (5)	0.0251 (4)	0.0137 (4)	0.0002 (4)	−0.0012 (3)	−0.0019 (3)
C20A	0.0345 (6)	0.0318 (6)	0.0201 (5)	0.0048 (5)	0.0019 (4)	−0.0052 (4)
Cl1B	0.01107 (8)	0.01674 (9)	0.01895 (9)	0.00106 (6)	0.00072 (7)	0.00006 (8)
Cl2B	0.01793 (10)	0.01100 (8)	0.02802 (12)	0.00259 (7)	−0.00158 (9)	−0.00183 (8)
O1B	0.0153 (3)	0.0157 (3)	0.0247 (3)	−0.0031 (2)	0.0026 (3)	0.0050 (3)
O2B	0.0180 (3)	0.0116 (3)	0.0310 (4)	−0.0035 (2)	−0.0040 (3)	−0.0011 (3)
C1B	0.0105 (3)	0.0119 (3)	0.0144 (3)	−0.0007 (3)	−0.0013 (3)	0.0003 (3)
C2B	0.0121 (3)	0.0109 (3)	0.0144 (3)	−0.0003 (3)	0.0000 (3)	0.0000 (3)
C3B	0.0111 (3)	0.0101 (3)	0.0127 (3)	−0.0005 (2)	0.0001 (3)	0.0002 (2)
C4B	0.0147 (4)	0.0107 (3)	0.0161 (4)	0.0009 (3)	0.0010 (3)	0.0008 (3)
C5B	0.0170 (4)	0.0150 (4)	0.0171 (4)	0.0041 (3)	−0.0003 (3)	0.0018 (3)
C6B	0.0131 (4)	0.0179 (4)	0.0204 (4)	0.0022 (3)	−0.0008 (3)	0.0012 (3)
C7B	0.0121 (3)	0.0143 (3)	0.0179 (4)	−0.0008 (3)	−0.0011 (3)	0.0000 (3)
C8B	0.0131 (3)	0.0106 (3)	0.0125 (3)	−0.0006 (3)	−0.0006 (3)	−0.0001 (3)
C9B	0.0133 (3)	0.0106 (3)	0.0146 (3)	−0.0014 (2)	−0.0009 (3)	−0.0003 (3)
C10B	0.0141 (4)	0.0095 (3)	0.0151 (3)	−0.0002 (3)	−0.0010 (3)	0.0003 (3)
C11B	0.0170 (4)	0.0165 (4)	0.0141 (4)	−0.0023 (3)	−0.0016 (3)	0.0020 (3)
C12B	0.0133 (3)	0.0152 (3)	0.0135 (3)	−0.0007 (3)	−0.0010 (3)	−0.0010 (3)
C13B	0.0150 (4)	0.0206 (4)	0.0171 (4)	−0.0023 (3)	−0.0006 (3)	−0.0048 (3)
C14B	0.0191 (4)	0.0309 (5)	0.0159 (4)	−0.0014 (4)	−0.0008 (3)	−0.0066 (4)
C15B	0.0284 (6)	0.0440 (7)	0.0212 (5)	−0.0049 (5)	−0.0017 (4)	−0.0138 (5)
C16B	0.0290 (6)	0.0425 (7)	0.0343 (6)	−0.0086 (5)	−0.0016 (5)	−0.0210 (6)
C17B	0.0306 (6)	0.0289 (6)	0.0390 (7)	−0.0119 (5)	−0.0010 (5)	−0.0137 (5)
C18B	0.0249 (5)	0.0227 (5)	0.0263 (5)	−0.0089 (4)	−0.0015 (4)	−0.0060 (4)
C19B	0.0276 (5)	0.0374 (6)	0.0142 (4)	−0.0013 (5)	−0.0022 (4)	−0.0009 (4)
C20B	0.0469 (8)	0.0441 (8)	0.0202 (5)	−0.0057 (7)	−0.0055 (5)	0.0065 (5)

Geometric parameters (Å, º) top

Cl1A—C1A	1.7682 (9)	Cl1B—C1B	1.7711 (9)
Cl2A—C10A	1.7702 (10)	Cl2B—C10B	1.7740 (10)
O1A—C2A	1.2208 (11)	O1B—C2B	1.2157 (12)
O2A—C9A	1.2168 (11)	O2B—C9B	1.2156 (11)
C1A—C12A	1.5276 (13)	C1B—C2B	1.5295 (13)
C1A—C2A	1.5278 (13)	C1B—C12B	1.5308 (14)
C1A—C10A	1.5952 (13)	C1B—C10B	1.5912 (13)
C2A—C3A	1.4780 (13)	C2B—C3B	1.4799 (13)
C3A—C4A	1.3936 (13)	C3B—C4B	1.3981 (13)
C3A—C8A	1.4062 (12)	C3B—C8B	1.4044 (12)
C4A—C5A	1.3921 (15)	C4B—C5B	1.3895 (15)
C4A—H4AA	0.93	C4B—H4BA	0.93
C5A—C6A	1.3952 (15)	C5B—C6B	1.3944 (15)
C5A—H5AA	0.93	C5B—H5BA	0.93
C6A—C7A	1.3913 (14)	C6B—C7B	1.3916 (14)
C6A—H6AA	0.93	C6B—H6BA	0.93
C7A—C8A	1.3945 (13)	C7B—C8B	1.3990 (13)
C7A—H7AA	0.93	C7B—H7BA	0.93
C8A—C9A	1.4906 (13)	C8B—C9B	1.4867 (12)
C9A—C10A	1.5369 (13)	C9B—C10B	1.5329 (13)
C10A—C11A	1.5080 (14)	C10B—C11B	1.5111 (14)
C11A—C12A	1.3526 (13)	C11B—C12B	1.3483 (14)
C11A—H11A	0.93	C11B—H11B	1.01
C12A—C13A	1.4569 (14)	C12B—C13B	1.4590 (14)
C13A—C18A	1.4022 (15)	C13B—C18B	1.3976 (16)
C13A—C14A	1.4122 (14)	C13B—C14B	1.4178 (15)
C14A—C15A	1.4027 (15)	C14B—C15B	1.4013 (16)
C14A—C19A	1.4307 (16)	C14B—C19B	1.4360 (19)
C15A—C16A	1.3875 (19)	C15B—C16B	1.384 (2)
C15A—H15A	0.93	C15B—H15B	0.93
C16A—C17A	1.3911 (18)	C16B—C17B	1.390 (2)
C16A—H16A	0.93	C16B—H16B	0.93
C17A—C18A	1.3951 (17)	C17B—C18B	1.3925 (17)
C17A—H17A	0.93	C17B—H17B	0.93
C18A—H18A	0.93	C18B—H18B	0.93
C19A—C20A	1.2016 (17)	C19B—C20B	1.190 (2)
C20A—H20A	0.97	C20B—H20B	0.99

C12A—C1A—C2A	117.68 (8)	C2B—C1B—C12B	118.15 (8)
C12A—C1A—C10A	84.96 (7)	C2B—C1B—C10B	115.20 (7)
C2A—C1A—C10A	115.17 (8)	C12B—C1B—C10B	85.12 (7)
C12A—C1A—Cl1A	111.96 (7)	C2B—C1B—Cl1B	109.27 (6)
C2A—C1A—Cl1A	109.73 (6)	C12B—C1B—Cl1B	111.71 (6)
C10A—C1A—Cl1A	115.64 (6)	C10B—C1B—Cl1B	115.89 (6)
O1A—C2A—C3A	121.93 (9)	O1B—C2B—C3B	121.81 (8)
O1A—C2A—C1A	122.18 (9)	O1B—C2B—C1B	122.11 (9)
C3A—C2A—C1A	115.87 (8)	C3B—C2B—C1B	116.07 (8)
C4A—C3A—C8A	120.46 (9)	C4B—C3B—C8B	120.32 (8)
C4A—C3A—C2A	118.43 (8)	C4B—C3B—C2B	118.15 (8)
C8A—C3A—C2A	121.01 (8)	C8B—C3B—C2B	121.46 (8)
C5A—C4A—C3A	119.73 (9)	C5B—C4B—C3B	119.68 (9)
C5A—C4A—H4AA	120.1	C5B—C4B—H4BA	120.2
C3A—C4A—H4AA	120.1	C3B—C4B—H4BA	120.2
C4A—C5A—C6A	120.05 (9)	C4B—C5B—C6B	120.28 (9)
C4A—C5A—H5AA	120.0	C4B—C5B—H5BA	119.9
C6A—C5A—H5AA	120.0	C6B—C5B—H5BA	119.9
C7A—C6A—C5A	120.24 (9)	C7B—C6B—C5B	120.27 (9)
C7A—C6A—H6AA	119.9	C7B—C6B—H6BA	119.9
C5A—C6A—H6AA	119.9	C5B—C6B—H6BA	119.9
C6A—C7A—C8A	120.27 (9)	C6B—C7B—C8B	120.06 (9)
C6A—C7A—H7AA	119.9	C6B—C7B—H7BA	120.0
C8A—C7A—H7AA	119.9	C8B—C7B—H7BA	120.0
C7A—C8A—C3A	119.21 (8)	C7B—C8B—C3B	119.38 (8)
C7A—C8A—C9A	119.22 (8)	C7B—C8B—C9B	118.89 (8)
C3A—C8A—C9A	121.49 (8)	C3B—C8B—C9B	121.71 (8)
O2A—C9A—C8A	122.09 (8)	O2B—C9B—C8B	122.13 (8)
O2A—C9A—C10A	120.53 (8)	O2B—C9B—C10B	120.52 (8)
C8A—C9A—C10A	116.99 (7)	C8B—C9B—C10B	117.01 (7)
C11A—C10A—C9A	109.57 (8)	C11B—C10B—C9B	110.24 (8)
C11A—C10A—C1A	85.77 (7)	C11B—C10B—C1B	85.66 (7)
C9A—C10A—C1A	116.59 (7)	C9B—C10B—C1B	117.36 (7)
C11A—C10A—Cl2A	115.92 (7)	C11B—C10B—Cl2B	114.97 (7)
C9A—C10A—Cl2A	110.30 (6)	C9B—C10B—Cl2B	110.36 (6)
C1A—C10A—Cl2A	116.64 (7)	C1B—C10B—Cl2B	116.16 (7)
C12A—C11A—C10A	94.88 (8)	C12B—C11B—C10B	95.06 (8)
C12A—C11A—H11A	139.2	C12B—C11B—H11B	133.6
C10A—C11A—H11A	123.9	C10B—C11B—H11B	131.0
C11A—C12A—C13A	137.08 (9)	C11B—C12B—C13B	136.65 (10)
C11A—C12A—C1A	94.17 (8)	C11B—C12B—C1B	94.03 (8)
C13A—C12A—C1A	128.72 (8)	C13B—C12B—C1B	129.30 (9)
C18A—C13A—C14A	119.00 (9)	C18B—C13B—C14B	119.02 (10)
C18A—C13A—C12A	119.23 (9)	C18B—C13B—C12B	119.99 (10)
C14A—C13A—C12A	121.72 (9)	C14B—C13B—C12B	120.99 (10)
C15A—C14A—C13A	119.38 (10)	C15B—C14B—C13B	119.45 (12)
C15A—C14A—C19A	118.86 (10)	C15B—C14B—C19B	118.28 (11)
C13A—C14A—C19A	121.75 (9)	C13B—C14B—C19B	122.25 (10)
C16A—C15A—C14A	120.89 (11)	C16B—C15B—C14B	120.47 (13)
C16A—C15A—H15A	119.6	C16B—C15B—H15B	119.8
C14A—C15A—H15A	119.6	C14B—C15B—H15B	119.8
C15A—C16A—C17A	119.93 (11)	C15B—C16B—C17B	120.39 (12)
C15A—C16A—H16A	120.0	C15B—C16B—H16B	119.8
C17A—C16A—H16A	120.0	C17B—C16B—H16B	119.8
C16A—C17A—C18A	119.98 (12)	C16B—C17B—C18B	119.91 (14)
C16A—C17A—H17A	120.0	C16B—C17B—H17B	120.0
C18A—C17A—H17A	120.0	C18B—C17B—H17B	120.0
C17A—C18A—C13A	120.79 (11)	C17B—C18B—C13B	120.74 (12)
C17A—C18A—H18A	119.6	C17B—C18B—H18B	119.6
C13A—C18A—H18A	119.6	C13B—C18B—H18B	119.6
C20A—C19A—C14A	177.43 (12)	C20B—C19B—C14B	176.29 (13)
C19A—C20A—H20A	166.1	C19B—C20B—H20B	174.3

C12A—C1A—C2A—O1A	116.09 (10)	C12B—C1B—C2B—O1B	113.89 (11)
C10A—C1A—C2A—O1A	−146.04 (9)	C10B—C1B—C2B—O1B	−147.77 (9)
Cl1A—C1A—C2A—O1A	−13.47 (12)	Cl1B—C1B—C2B—O1B	−15.26 (12)
C12A—C1A—C2A—C3A	−62.10 (11)	C12B—C1B—C2B—C3B	−64.99 (11)
C10A—C1A—C2A—C3A	35.77 (11)	C10B—C1B—C2B—C3B	33.36 (11)
Cl1A—C1A—C2A—C3A	168.34 (7)	Cl1B—C1B—C2B—C3B	165.86 (7)
O1A—C2A—C3A—C4A	−26.36 (14)	O1B—C2B—C3B—C4B	−25.97 (14)
C1A—C2A—C3A—C4A	151.84 (9)	C1B—C2B—C3B—C4B	152.91 (8)
O1A—C2A—C3A—C8A	150.14 (10)	O1B—C2B—C3B—C8B	151.02 (10)
C1A—C2A—C3A—C8A	−31.67 (12)	C1B—C2B—C3B—C8B	−30.10 (12)
C8A—C3A—C4A—C5A	1.06 (15)	C8B—C3B—C4B—C5B	1.07 (14)
C2A—C3A—C4A—C5A	177.57 (9)	C2B—C3B—C4B—C5B	178.10 (9)
C3A—C4A—C5A—C6A	−1.82 (15)	C3B—C4B—C5B—C6B	−1.63 (15)
C4A—C5A—C6A—C7A	1.13 (16)	C4B—C5B—C6B—C7B	0.90 (16)
C5A—C6A—C7A—C8A	0.33 (16)	C5B—C6B—C7B—C8B	0.41 (15)
C6A—C7A—C8A—C3A	−1.08 (15)	C6B—C7B—C8B—C3B	−0.96 (14)
C6A—C7A—C8A—C9A	−177.76 (9)	C6B—C7B—C8B—C9B	−179.00 (9)
C4A—C3A—C8A—C7A	0.39 (14)	C4B—C3B—C8B—C7B	0.22 (13)
C2A—C3A—C8A—C7A	−176.03 (9)	C2B—C3B—C8B—C7B	−176.71 (9)
C4A—C3A—C8A—C9A	176.99 (9)	C4B—C3B—C8B—C9B	178.20 (9)
C2A—C3A—C8A—C9A	0.57 (14)	C2B—C3B—C8B—C9B	1.27 (14)
C7A—C8A—C9A—O2A	13.92 (15)	C7B—C8B—C9B—O2B	13.62 (15)
C3A—C8A—C9A—O2A	−162.68 (10)	C3B—C8B—C9B—O2B	−164.37 (10)
C7A—C8A—C9A—C10A	−158.93 (9)	C7B—C8B—C9B—C10B	−159.69 (9)
C3A—C8A—C9A—C10A	24.47 (13)	C3B—C8B—C9B—C10B	22.32 (13)
O2A—C9A—C10A—C11A	−95.23 (11)	O2B—C9B—C10B—C11B	−93.93 (11)
C8A—C9A—C10A—C11A	77.74 (10)	C8B—C9B—C10B—C11B	79.50 (10)
O2A—C9A—C10A—C1A	169.58 (9)	O2B—C9B—C10B—C1B	170.33 (9)
C8A—C9A—C10A—C1A	−17.45 (12)	C8B—C9B—C10B—C1B	−16.24 (12)
O2A—C9A—C10A—Cl2A	33.54 (12)	O2B—C9B—C10B—Cl2B	34.15 (12)
C8A—C9A—C10A—Cl2A	−153.50 (7)	C8B—C9B—C10B—Cl2B	−152.42 (7)
C12A—C1A—C10A—C11A	−3.21 (7)	C2B—C1B—C10B—C11B	−121.39 (9)
C2A—C1A—C10A—C11A	−121.49 (8)	C12B—C1B—C10B—C11B	−2.51 (7)
Cl1A—C1A—C10A—C11A	108.76 (7)	Cl1B—C1B—C10B—C11B	109.28 (7)
C12A—C1A—C10A—C9A	106.58 (9)	C2B—C1B—C10B—C9B	−10.82 (12)
C2A—C1A—C10A—C9A	−11.70 (12)	C12B—C1B—C10B—C9B	108.07 (9)
Cl1A—C1A—C10A—C9A	−141.45 (7)	Cl1B—C1B—C10B—C9B	−140.15 (7)
C12A—C1A—C10A—Cl2A	−120.17 (7)	C2B—C1B—C10B—Cl2B	122.87 (8)
C2A—C1A—C10A—Cl2A	121.55 (8)	C12B—C1B—C10B—Cl2B	−118.25 (7)
Cl1A—C1A—C10A—Cl2A	−8.19 (10)	Cl1B—C1B—C10B—Cl2B	−6.46 (10)
C9A—C10A—C11A—C12A	−113.12 (8)	C9B—C10B—C11B—C12B	−114.75 (8)
C1A—C10A—C11A—C12A	3.62 (8)	C1B—C10B—C11B—C12B	2.85 (8)
Cl2A—C10A—C11A—C12A	121.27 (8)	Cl2B—C10B—C11B—C12B	119.74 (8)
C10A—C11A—C12A—C13A	174.32 (12)	C10B—C11B—C12B—C13B	178.76 (12)
C10A—C11A—C12A—C1A	−3.79 (8)	C10B—C11B—C12B—C1B	−2.96 (8)
C2A—C1A—C12A—C11A	119.42 (9)	C2B—C1B—C12B—C11B	118.85 (9)
C10A—C1A—C12A—C11A	3.58 (7)	C10B—C1B—C12B—C11B	2.81 (8)
Cl1A—C1A—C12A—C11A	−112.07 (7)	Cl1B—C1B—C12B—C11B	−113.14 (7)
C2A—C1A—C12A—C13A	−58.93 (13)	C2B—C1B—C12B—C13B	−62.68 (13)
C10A—C1A—C12A—C13A	−174.77 (10)	C10B—C1B—C12B—C13B	−178.72 (10)
Cl1A—C1A—C12A—C13A	69.58 (12)	Cl1B—C1B—C12B—C13B	65.33 (12)
C11A—C12A—C13A—C18A	−166.50 (13)	C11B—C12B—C13B—C18B	−162.10 (13)
C1A—C12A—C13A—C18A	11.08 (16)	C1B—C12B—C13B—C18B	20.12 (16)
C11A—C12A—C13A—C14A	11.11 (19)	C11B—C12B—C13B—C14B	18.36 (19)
C1A—C12A—C13A—C14A	−171.31 (10)	C1B—C12B—C13B—C14B	−159.42 (10)
C18A—C13A—C14A—C15A	1.10 (16)	C18B—C13B—C14B—C15B	0.55 (17)
C12A—C13A—C14A—C15A	−176.52 (10)	C12B—C13B—C14B—C15B	−179.90 (11)
C18A—C13A—C14A—C19A	179.84 (11)	C18B—C13B—C14B—C19B	−177.46 (12)
C12A—C13A—C14A—C19A	2.23 (16)	C12B—C13B—C14B—C19B	2.08 (17)
C13A—C14A—C15A—C16A	−0.12 (18)	C13B—C14B—C15B—C16B	0.5 (2)
C19A—C14A—C15A—C16A	−178.91 (12)	C19B—C14B—C15B—C16B	178.57 (13)
C14A—C15A—C16A—C17A	−0.1 (2)	C14B—C15B—C16B—C17B	−0.5 (2)
C15A—C16A—C17A—C18A	−0.7 (2)	C15B—C16B—C17B—C18B	−0.6 (2)
C16A—C17A—C18A—C13A	1.7 (2)	C16B—C17B—C18B—C13B	1.7 (2)
C14A—C13A—C18A—C17A	−1.91 (19)	C14B—C13B—C18B—C17B	−1.62 (18)
C12A—C13A—C18A—C17A	175.76 (12)	C12B—C13B—C18B—C17B	178.83 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5AA···Cl1Aⁱ	0.93	2.78	3.603 (1)	148
C7A—H7AA···Cl1Aⁱⁱ	0.93	2.72	3.651 (1)	177
C4B—H4BA···Cl2Bⁱⁱⁱ	0.93	2.83	3.715 (1)	160
C5B—H5BA···Cl1B^iv	0.93	2.77	3.584 (1)	147
C7B—H7BA···Cl1B^v	0.93	2.75	3.682 (1)	176
C20A—H20A···Cl1B^vi	0.97	2.80	3.607 (1)	142
C15A—H15A···Cg1^vii	0.93	2.55	3.479 (1)	175

Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x+1/2, −y+1/2, z; (iii) x, y+1, z; (iv) x−1/2, −y+5/2, z; (v) x−1/2, −y+3/2, z; (vi) −x+1, −y+1, z−1/2; (vii) −x+1/2, y−1/2, z−1/2.

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