1,3-trans-1,4-cis-1,2-Bis(2,4-dichloro­phen­yl)-1,2,3,3a,8,8a-hexa­hydro­benzo[e]penta­lene-3-spiro-2'-indan-3a,1'-diol acetone solvate

The title compound, C₃₂H₂₄Cl₄O₂·C₃H₆O, was obtained as a by-product of the reaction of 2-(2',4'-dichloro­benzal)-1-inden-1-one induced by a low-valent titanium reagent (TiCl₄/Zn). Each of the fused cyclo­pentane rings adopts an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.056
• wR factor = 0.170
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C34
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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

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

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S1. Comment

The spiro[4.4]nonane skeleton has been found in many ligands for highly enantioselective hydrogenation (Lin et al., 2004). Compounds containing the spiro[4.4]nonane skeleton show biological activities such as anticonvulsant (Obniska et al., 2003). Low-valent titanium reagents have an exceedingly high ability to promote the reductive coupling of carbonyl compounds and are attracting increasing interest in organic synthesis (McMurry, 1983; Shi et al., 1993, 1997, 1998, 2003). We report here the synthesis and the crystal structure of the title compound, (I).

In (I), the C1/C9/C10–C12 cyclopentane ring is the new ring formed by dimerization of 2-(2',4'-chlorobenzal)-1-indenone induced by low-valent titanium reagent. This ring adopts an envelope conformation; atoms C1, C9, C10 and C11 are coplanar, while atom C12 deviates from this plane by 0.672 (2) Å. The C1/C2/C7–C9 cyclopentane ring adopts an envelope conformation as well, atom C9 deviating from the C1/C2/C7/C8 plane by 0.440 (3) Å. The dihedral angle between the two 2,4-dichlorophenyl rings is 78.4 (5)°. In the crystal structure, classical O—H···O hydrogen bonds (Table 2) connect adjacent molecules into centrosymmetric dimers (Fig. 2).

S2. Experimental

Compound (I), as a by-product, was prepared by the dimerization of 2-(2',4'-dichlorobenzal)-1-indenone (1.45 g, 5 mmol) induced by low-valent titanium reagent (TiCl₄/Zn). Yield of (I) 16%, m.p. 516–518 K. The main product was 2,2'-[1,2-bis(2,4-dichlorophenyl)ethane-1,2-diyl] bis(1-tetralone). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a petroleum ether/acetone solution. ¹H NMR: 2.09 (2H, s, C^3'—H), 2.51–2.57 (1H, m, C⁶—H), 2.89–2.96 (2H, m, C⁶—H, C⁵—H), 3.03 (1H, dd, J₁ = 16.8 Hz, J₂ = 8.4 Hz, C⁴—H), 3.17 (1H, d, J = 16.8 Hz, C³—H), 4.09–4.12 (1H, m, C^1'—H), 5.31 (1H, d, J = 12.4 Hz, OH), 6.09 (1H, s, OH), 6.43 (1H, d, J = 8.0 Hz, ArH), 6.88 (1H, t, J = 7.2 Hz, ArH), 7.08 (1H, d, J = 7.6 Hz, ArH), 7.21–7.27 (3H, m, ArH), 7.33–7.37 (2H, m, ArH), 7.46–7.52 (3H, m, ArH), 7.58–7.64 (2H, m, ArH), 7.86 (1H, d, J = 8.4 Hz, ArH).

S3. Refinement

The hydroxy H atoms were located from difference Fourier maps and refined isotropically. H atoms on C atoms were positioned geometrically and treated as riding on their parent C atoms, with C—H distances in the range 0.93–0.98 Å, and with U_iso(H) = 1.2U_eq(C), except for the methyl H atoms, for which U_iso(H) = 1.5U_eq(C).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing of (I). Dashed lines indicated hydrogen bonds. H atoms have been omitted unless they are involved in hydrogen bonding.

1,3-trans-1,4-cis-1,2-Bis(2,4-dichlorophenyl)-1,2,3,3a,8,8a- hexahydrobenzo[e]pentalene-3-spiro-2'-indan-3a,1'-diol acetone solvate

Crystal data

C32H24Cl4O2·C3H6O	F(000) = 2656
Mr = 640.39	Dx = 1.376 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 31.620 (8) Å	Cell parameters from 2726 reflections
b = 10.443 (3) Å	θ = 2.5–20.6°
c = 20.993 (5) Å	µ = 0.42 mm^−1
β = 116.931 (4)°	T = 293 K
V = 6180 (3) Å^3	Block, colorless
Z = 8	0.39 × 0.37 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5442 independent reflections
Radiation source: fine-focus sealed tube	2710 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ϕ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→37
Tmin = 0.854, Tmax = 0.940	k = −12→12
15854 measured reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0568P)^2 + 14.254P] where P = (Fo^2 + 2Fc^2)/3
5442 reflections	(Δ/σ)max < 0.001
387 parameters	Δρmax = 0.68 e Å^−3
1 restraint	Δρmin = −0.53 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.15033 (7)	1.15917 (14)	0.37687 (12)	0.1298 (8)
Cl2	−0.02784 (6)	1.23222 (16)	0.33080 (8)	0.1123 (6)
Cl3	0.03615 (4)	0.59628 (13)	0.20895 (6)	0.0776 (4)
Cl4	0.05649 (6)	0.89088 (18)	0.01949 (7)	0.1077 (6)
O1	0.20708 (9)	0.6255 (3)	0.50390 (15)	0.0511 (8)
O2	0.22077 (11)	0.7964 (3)	0.36507 (17)	0.0581 (8)
O3	0.21534 (17)	0.6293 (4)	0.0346 (3)	0.1339 (19)
C1	0.16376 (13)	0.6767 (3)	0.4485 (2)	0.0414 (10)
C2	0.12281 (14)	0.6386 (4)	0.4647 (2)	0.0465 (10)
C3	0.09913 (15)	0.5220 (4)	0.4541 (2)	0.0611 (12)
H3	0.1049	0.4560	0.4292	0.073*
C4	0.06693 (17)	0.5063 (5)	0.4812 (3)	0.0752 (15)
H4	0.0512	0.4285	0.4748	0.090*
C5	0.05775 (17)	0.6029 (6)	0.5175 (3)	0.0760 (15)
H5	0.0357	0.5904	0.5348	0.091*
C6	0.08113 (16)	0.7187 (5)	0.5283 (2)	0.0651 (13)
H6	0.0752	0.7842	0.5533	0.078*
C7	0.11343 (14)	0.7357 (4)	0.5015 (2)	0.0492 (10)
C8	0.14393 (15)	0.8501 (4)	0.5086 (2)	0.0521 (11)
H8A	0.1693	0.8576	0.5569	0.062*
H8B	0.1253	0.9283	0.4963	0.062*
C9	0.16359 (14)	0.8234 (3)	0.45568 (19)	0.0425 (10)
H9	0.1960	0.8565	0.4744	0.051*
C10	0.13303 (13)	0.8714 (3)	0.37660 (19)	0.0407 (9)
H10	0.1546	0.9203	0.3640	0.049*
C11	0.11942 (13)	0.7494 (3)	0.32932 (19)	0.0394 (9)
H11	0.0903	0.7170	0.3293	0.047*
C12	0.15865 (13)	0.6511 (3)	0.3729 (2)	0.0412 (9)
C13	0.20687 (14)	0.6685 (4)	0.3699 (2)	0.0490 (10)
H13	0.2318	0.6305	0.4133	0.059*
C14	0.20164 (16)	0.5864 (4)	0.3077 (2)	0.0574 (12)
C15	0.2286 (2)	0.5869 (6)	0.2710 (3)	0.0848 (16)
H15	0.2523	0.6475	0.2811	0.102*
C16	0.2193 (3)	0.4948 (7)	0.2191 (4)	0.114 (2)
H16	0.2376	0.4917	0.1947	0.136*
C17	0.1835 (3)	0.4080 (7)	0.2033 (4)	0.112 (2)
H17	0.1772	0.3483	0.1672	0.135*
C18	0.1562 (2)	0.4068 (5)	0.2398 (3)	0.0861 (17)
H18	0.1320	0.3471	0.2288	0.103*
C19	0.16608 (16)	0.4971 (4)	0.2931 (2)	0.0590 (12)
C20	0.14571 (15)	0.5123 (4)	0.3447 (2)	0.0528 (11)
H20A	0.1596	0.4510	0.3835	0.063*
H20B	0.1116	0.5004	0.3209	0.063*
C21	0.09211 (14)	0.9598 (4)	0.36405 (19)	0.0436 (10)
C22	0.09676 (17)	1.0913 (4)	0.3632 (2)	0.0618 (12)
C23	0.0601 (2)	1.1749 (5)	0.3528 (3)	0.0756 (15)
H23	0.0647	1.2629	0.3529	0.091*
C24	0.0179 (2)	1.1274 (5)	0.3424 (2)	0.0663 (14)
C25	0.01083 (17)	0.9985 (5)	0.3415 (2)	0.0687 (14)
H25	−0.0185	0.9661	0.3337	0.082*
C26	0.04771 (16)	0.9167 (4)	0.3524 (2)	0.0576 (12)
H26	0.0426	0.8290	0.3519	0.069*
C27	0.10671 (13)	0.7764 (4)	0.2516 (2)	0.0435 (10)
C28	0.06932 (14)	0.7157 (4)	0.1952 (2)	0.0493 (10)
C29	0.05481 (16)	0.7479 (5)	0.1243 (2)	0.0632 (13)
H29	0.0301	0.7037	0.0880	0.076*
C30	0.07716 (18)	0.8451 (5)	0.1085 (2)	0.0688 (14)
C31	0.11483 (18)	0.9074 (5)	0.1617 (2)	0.0720 (14)
H31	0.1304	0.9728	0.1507	0.086*
C32	0.12920 (16)	0.8714 (4)	0.2315 (2)	0.0569 (12)
H32	0.1552	0.9127	0.2671	0.068*
C33	0.1671 (3)	0.7175 (10)	0.0778 (5)	0.199 (5)
H33A	0.1520	0.6352	0.0664	0.298*
H33B	0.1452	0.7820	0.0490	0.298*
H33C	0.1772	0.7359	0.1274	0.298*
C34	0.20875 (19)	0.7165 (6)	0.0634 (3)	0.0874 (18)
C35	0.2335 (3)	0.8345 (8)	0.0798 (6)	0.210 (5)
H35A	0.2606	0.8278	0.0708	0.315*
H35B	0.2439	0.8546	0.1293	0.315*
H35C	0.2129	0.9010	0.0506	0.315*
H1	0.2051 (18)	0.551 (5)	0.515 (3)	0.090 (19)*
H2	0.2415 (17)	0.818 (4)	0.405 (2)	0.072 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1248 (14)	0.0468 (8)	0.227 (2)	−0.0302 (8)	0.0879 (15)	−0.0129 (11)
Cl2	0.1291 (13)	0.1073 (12)	0.0830 (10)	0.0689 (11)	0.0327 (9)	−0.0021 (9)
Cl3	0.0728 (8)	0.0832 (9)	0.0600 (7)	−0.0364 (7)	0.0154 (6)	−0.0033 (6)
Cl4	0.1255 (13)	0.1452 (15)	0.0448 (7)	−0.0195 (11)	0.0320 (8)	0.0140 (8)
O1	0.0447 (17)	0.0442 (19)	0.0482 (17)	−0.0042 (14)	0.0068 (13)	0.0080 (14)
O2	0.0562 (19)	0.063 (2)	0.0507 (19)	−0.0190 (16)	0.0206 (16)	−0.0060 (16)
O3	0.130 (4)	0.068 (3)	0.199 (5)	−0.009 (3)	0.069 (4)	−0.049 (3)
C1	0.039 (2)	0.036 (2)	0.042 (2)	−0.0031 (17)	0.0117 (18)	0.0049 (17)
C2	0.044 (2)	0.048 (2)	0.040 (2)	−0.003 (2)	0.0121 (18)	0.0082 (19)
C3	0.056 (3)	0.061 (3)	0.062 (3)	−0.009 (2)	0.023 (2)	0.006 (2)
C4	0.060 (3)	0.075 (4)	0.086 (4)	−0.016 (3)	0.029 (3)	0.016 (3)
C5	0.053 (3)	0.105 (5)	0.071 (3)	−0.004 (3)	0.030 (3)	0.018 (3)
C6	0.063 (3)	0.082 (4)	0.053 (3)	0.006 (3)	0.028 (2)	0.012 (3)
C7	0.049 (2)	0.060 (3)	0.036 (2)	0.001 (2)	0.0167 (19)	0.009 (2)
C8	0.061 (3)	0.056 (3)	0.034 (2)	0.002 (2)	0.017 (2)	0.002 (2)
C9	0.048 (2)	0.035 (2)	0.038 (2)	−0.0057 (17)	0.0134 (18)	−0.0004 (17)
C10	0.047 (2)	0.034 (2)	0.038 (2)	−0.0051 (18)	0.0167 (18)	0.0025 (17)
C11	0.041 (2)	0.035 (2)	0.039 (2)	−0.0042 (17)	0.0157 (17)	−0.0020 (17)
C12	0.038 (2)	0.034 (2)	0.047 (2)	−0.0030 (17)	0.0163 (18)	−0.0034 (18)
C13	0.048 (2)	0.045 (3)	0.050 (2)	−0.0029 (19)	0.020 (2)	−0.004 (2)
C14	0.055 (3)	0.057 (3)	0.057 (3)	0.004 (2)	0.023 (2)	−0.010 (2)
C15	0.085 (4)	0.102 (4)	0.082 (4)	−0.008 (3)	0.050 (3)	−0.022 (3)
C16	0.116 (5)	0.135 (6)	0.109 (5)	−0.012 (5)	0.068 (4)	−0.051 (5)
C17	0.122 (6)	0.113 (6)	0.106 (5)	0.000 (5)	0.055 (5)	−0.055 (4)
C18	0.093 (4)	0.066 (4)	0.087 (4)	0.001 (3)	0.030 (3)	−0.029 (3)
C19	0.063 (3)	0.044 (3)	0.062 (3)	0.004 (2)	0.021 (2)	−0.011 (2)
C20	0.052 (3)	0.039 (2)	0.058 (3)	−0.0037 (19)	0.016 (2)	−0.006 (2)
C21	0.056 (3)	0.036 (2)	0.032 (2)	−0.0030 (19)	0.0140 (18)	−0.0015 (17)
C22	0.082 (3)	0.036 (2)	0.062 (3)	−0.003 (2)	0.028 (3)	−0.003 (2)
C23	0.109 (5)	0.041 (3)	0.069 (3)	0.009 (3)	0.033 (3)	−0.003 (2)
C24	0.090 (4)	0.061 (3)	0.038 (2)	0.026 (3)	0.020 (2)	−0.002 (2)
C25	0.065 (3)	0.071 (4)	0.065 (3)	0.007 (3)	0.025 (2)	−0.010 (3)
C26	0.059 (3)	0.047 (3)	0.061 (3)	0.002 (2)	0.023 (2)	−0.003 (2)
C27	0.047 (2)	0.041 (2)	0.042 (2)	−0.0032 (18)	0.0202 (19)	−0.0006 (18)
C28	0.050 (2)	0.050 (3)	0.044 (2)	−0.008 (2)	0.018 (2)	−0.006 (2)
C29	0.065 (3)	0.078 (3)	0.042 (3)	−0.013 (3)	0.020 (2)	−0.013 (2)
C30	0.078 (3)	0.088 (4)	0.041 (3)	−0.010 (3)	0.028 (2)	0.001 (3)
C31	0.089 (4)	0.081 (4)	0.052 (3)	−0.018 (3)	0.036 (3)	0.008 (3)
C32	0.064 (3)	0.062 (3)	0.045 (2)	−0.015 (2)	0.025 (2)	−0.003 (2)
C33	0.160 (9)	0.261 (13)	0.187 (10)	−0.051 (8)	0.089 (8)	−0.088 (9)
C34	0.062 (4)	0.068 (4)	0.115 (5)	−0.001 (3)	0.026 (3)	−0.024 (3)
C35	0.212 (10)	0.120 (7)	0.341 (15)	−0.082 (7)	0.163 (10)	−0.132 (9)

Geometric parameters (Å, º)

Cl1—C22	1.736 (5)	C14—C19	1.384 (6)
Cl2—C24	1.741 (5)	C15—C16	1.383 (7)
Cl3—C28	1.736 (4)	C15—H15	0.9300
Cl4—C30	1.744 (5)	C16—C17	1.370 (9)
O1—C1	1.439 (4)	C16—H16	0.9300
O1—H1	0.82 (5)	C17—C18	1.389 (8)
O2—C13	1.423 (5)	C17—H17	0.9300
O2—H2	0.83 (5)	C18—C19	1.388 (6)
O3—C34	1.162 (6)	C18—H18	0.9300
C1—C2	1.532 (5)	C19—C20	1.498 (6)
C1—C9	1.539 (5)	C20—H20A	0.9700
C1—C12	1.544 (5)	C20—H20B	0.9700
C2—C7	1.386 (6)	C21—C22	1.382 (5)
C2—C3	1.393 (6)	C21—C26	1.387 (6)
C3—C4	1.384 (6)	C22—C23	1.387 (7)
C3—H3	0.9300	C23—C24	1.346 (7)
C4—C5	1.372 (7)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.364 (7)
C5—C6	1.381 (7)	C25—C26	1.378 (6)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.383 (6)	C26—H26	0.9300
C6—H6	0.9300	C27—C28	1.391 (5)
C7—C8	1.500 (6)	C27—C32	1.393 (5)
C8—C9	1.524 (5)	C28—C29	1.385 (6)
C8—H8A	0.9700	C29—C30	1.361 (6)
C8—H8B	0.9700	C29—H29	0.9300
C9—C10	1.578 (5)	C30—C31	1.372 (6)
C9—H9	0.9800	C31—C32	1.376 (6)
C10—C21	1.512 (5)	C31—H31	0.9300
C10—C11	1.552 (5)	C32—H32	0.9300
C10—H10	0.9800	C33—C34	1.477 (9)
C11—C27	1.519 (5)	C33—H33A	0.9600
C11—C12	1.549 (5)	C33—H33B	0.9600
C11—H11	0.9800	C33—H33C	0.9600
C12—C20	1.549 (5)	C34—C35	1.417 (9)
C12—C13	1.565 (5)	C35—H35A	0.9600
C13—C14	1.506 (6)	C35—H35B	0.9600
C13—H13	0.9800	C35—H35C	0.9600
C14—C15	1.383 (6)
C1—O1—H1	114 (4)	C17—C16—H16	119.8
C13—O2—H2	108 (3)	C15—C16—H16	119.8
O1—C1—C2	108.4 (3)	C16—C17—C18	121.7 (6)
O1—C1—C9	109.6 (3)	C16—C17—H17	119.2
C2—C1—C9	101.3 (3)	C18—C17—H17	119.2
O1—C1—C12	112.6 (3)	C19—C18—C17	118.0 (5)
C2—C1—C12	118.5 (3)	C19—C18—H18	121.0
C9—C1—C12	105.6 (3)	C17—C18—H18	121.0
C7—C2—C3	119.6 (4)	C14—C19—C18	120.0 (5)
C7—C2—C1	110.4 (3)	C14—C19—C20	109.9 (4)
C3—C2—C1	129.7 (4)	C18—C19—C20	129.9 (5)
C4—C3—C2	118.7 (5)	C19—C20—C12	104.4 (3)
C4—C3—H3	120.6	C19—C20—H20A	110.9
C2—C3—H3	120.6	C12—C20—H20A	110.9
C5—C4—C3	121.4 (5)	C19—C20—H20B	110.9
C5—C4—H4	119.3	C12—C20—H20B	110.9
C3—C4—H4	119.3	H20A—C20—H20B	108.9
C4—C5—C6	120.2 (5)	C22—C21—C26	115.2 (4)
C4—C5—H5	119.9	C22—C21—C10	121.4 (4)
C6—C5—H5	119.9	C26—C21—C10	123.4 (4)
C5—C6—C7	119.0 (5)	C21—C22—C23	122.8 (5)
C5—C6—H6	120.5	C21—C22—Cl1	120.3 (4)
C7—C6—H6	120.5	C23—C22—Cl1	116.8 (4)
C6—C7—C2	121.1 (4)	C24—C23—C22	119.3 (5)
C6—C7—C8	128.5 (4)	C24—C23—H23	120.4
C2—C7—C8	110.4 (4)	C22—C23—H23	120.4
C7—C8—C9	103.7 (3)	C23—C24—C25	120.7 (5)
C7—C8—H8A	111.0	C23—C24—Cl2	119.4 (4)
C9—C8—H8A	111.0	C25—C24—Cl2	119.8 (5)
C7—C8—H8B	111.0	C24—C25—C26	119.2 (5)
C9—C8—H8B	111.0	C24—C25—H25	120.4
H8A—C8—H8B	109.0	C26—C25—H25	120.4
C8—C9—C1	105.9 (3)	C25—C26—C21	122.8 (4)
C8—C9—C10	116.8 (3)	C25—C26—H26	118.6
C1—C9—C10	104.0 (3)	C21—C26—H26	118.6
C8—C9—H9	109.9	C28—C27—C32	114.8 (4)
C1—C9—H9	109.9	C28—C27—C11	122.7 (3)
C10—C9—H9	109.9	C32—C27—C11	122.3 (3)
C21—C10—C11	115.0 (3)	C29—C28—C27	123.0 (4)
C21—C10—C9	116.4 (3)	C29—C28—Cl3	115.0 (3)
C11—C10—C9	105.8 (3)	C27—C28—Cl3	122.0 (3)
C21—C10—H10	106.3	C30—C29—C28	119.1 (4)
C11—C10—H10	106.3	C30—C29—H29	120.4
C9—C10—H10	106.3	C28—C29—H29	120.4
C27—C11—C12	120.6 (3)	C29—C30—C31	120.7 (4)
C27—C11—C10	113.3 (3)	C29—C30—Cl4	118.8 (4)
C12—C11—C10	104.5 (3)	C31—C30—Cl4	120.5 (4)
C27—C11—H11	105.8	C30—C31—C32	118.9 (4)
C12—C11—H11	105.8	C30—C31—H31	120.5
C10—C11—H11	105.8	C32—C31—H31	120.5
C1—C12—C20	116.2 (3)	C31—C32—C27	123.3 (4)
C1—C12—C11	100.1 (3)	C31—C32—H32	118.3
C20—C12—C11	113.1 (3)	C27—C32—H32	118.3
C1—C12—C13	111.8 (3)	C34—C33—H33A	109.5
C20—C12—C13	100.8 (3)	C34—C33—H33B	109.5
C11—C12—C13	115.7 (3)	H33A—C33—H33B	109.5
O2—C13—C14	112.9 (4)	C34—C33—H33C	109.5
O2—C13—C12	116.7 (3)	H33A—C33—H33C	109.5
C14—C13—C12	104.0 (3)	H33B—C33—H33C	109.5
O2—C13—H13	107.6	O3—C34—C35	126.7 (7)
C14—C13—H13	107.6	O3—C34—C33	119.9 (6)
C12—C13—H13	107.6	C35—C34—C33	112.9 (7)
C15—C14—C19	121.5 (4)	C34—C35—H35A	109.5
C15—C14—C13	128.8 (4)	C34—C35—H35B	109.5
C19—C14—C13	109.6 (4)	H35A—C35—H35B	109.5
C14—C15—C16	118.3 (6)	C34—C35—H35C	109.5
C14—C15—H15	120.9	H35A—C35—H35C	109.5
C16—C15—H15	120.9	H35B—C35—H35C	109.5
C17—C16—C15	120.5 (6)
O1—C1—C2—C7	94.8 (4)	C20—C12—C13—C14	31.2 (4)
C9—C1—C2—C7	−20.2 (4)	O2—C13—C14—C15	36.2 (7)
C12—C1—C2—C7	−135.1 (3)	C12—C13—C14—C15	164.3 (5)
O1—C1—C2—C3	−78.3 (5)	O2—C13—C14—C19	−147.5 (4)
C9—C1—C2—C3	166.7 (4)	C12—C13—C14—C19	−19.9 (4)
C12—C1—C2—C3	51.8 (6)	C19—C14—C15—C16	−0.5 (8)
C7—C2—C3—C4	−0.5 (6)	C13—C14—C15—C16	174.9 (5)
C1—C2—C3—C4	172.1 (4)	C14—C15—C16—C17	1.9 (10)
C2—C3—C4—C5	0.6 (7)	C15—C16—C17—C18	−1.8 (11)
C3—C4—C5—C6	−0.7 (8)	C16—C17—C18—C19	0.3 (10)
C4—C5—C6—C7	0.7 (7)	C15—C14—C19—C18	−1.1 (7)
C5—C6—C7—C2	−0.5 (6)	C13—C14—C19—C18	−177.2 (4)
C5—C6—C7—C8	−177.8 (4)	C15—C14—C19—C20	175.3 (4)
C3—C2—C7—C6	0.4 (6)	C13—C14—C19—C20	−0.8 (5)
C1—C2—C7—C6	−173.4 (4)	C17—C18—C19—C14	1.1 (8)
C3—C2—C7—C8	178.1 (3)	C17—C18—C19—C20	−174.4 (5)
C1—C2—C7—C8	4.2 (4)	C14—C19—C20—C12	21.5 (5)
C6—C7—C8—C9	−168.6 (4)	C18—C19—C20—C12	−162.6 (5)
C2—C7—C8—C9	13.9 (4)	C1—C12—C20—C19	−152.7 (3)
C7—C8—C9—C1	−26.3 (4)	C11—C12—C20—C19	92.4 (4)
C7—C8—C9—C10	88.8 (4)	C13—C12—C20—C19	−31.7 (4)
O1—C1—C9—C8	−86.1 (4)	C11—C10—C21—C22	−139.5 (4)
C2—C1—C9—C8	28.1 (4)	C9—C10—C21—C22	96.0 (5)
C12—C1—C9—C8	152.2 (3)	C11—C10—C21—C26	40.2 (5)
O1—C1—C9—C10	150.3 (3)	C9—C10—C21—C26	−84.3 (5)
C2—C1—C9—C10	−95.6 (3)	C26—C21—C22—C23	1.1 (6)
C12—C1—C9—C10	28.6 (4)	C10—C21—C22—C23	−179.2 (4)
C8—C9—C10—C21	10.8 (5)	C26—C21—C22—Cl1	−179.9 (3)
C1—C9—C10—C21	127.1 (3)	C10—C21—C22—Cl1	−0.1 (6)
C8—C9—C10—C11	−118.3 (4)	C21—C22—C23—C24	−0.5 (7)
C1—C9—C10—C11	−2.0 (4)	Cl1—C22—C23—C24	−179.6 (4)
C21—C10—C11—C27	72.0 (4)	C22—C23—C24—C25	−0.6 (7)
C9—C10—C11—C27	−158.0 (3)	C22—C23—C24—Cl2	178.9 (4)
C21—C10—C11—C12	−154.9 (3)	C23—C24—C25—C26	0.9 (7)
C9—C10—C11—C12	−24.9 (4)	Cl2—C24—C25—C26	−178.5 (3)
O1—C1—C12—C11	−163.2 (3)	C24—C25—C26—C21	−0.2 (7)
C2—C1—C12—C11	68.9 (4)	C22—C21—C26—C25	−0.7 (6)
C9—C1—C12—C11	−43.7 (4)	C10—C21—C26—C25	179.5 (4)
O1—C1—C12—C20	74.7 (4)	C12—C11—C27—C28	95.6 (5)
C2—C1—C12—C20	−53.2 (5)	C10—C11—C27—C28	−139.5 (4)
C9—C1—C12—C20	−165.8 (3)	C12—C11—C27—C32	−89.8 (5)
O1—C1—C12—C13	−40.1 (4)	C10—C11—C27—C32	35.0 (5)
C2—C1—C12—C13	−168.1 (3)	C32—C27—C28—C29	−0.9 (6)
C9—C1—C12—C13	79.4 (4)	C11—C27—C28—C29	174.1 (4)
C27—C11—C12—C1	170.5 (3)	C32—C27—C28—Cl3	−179.0 (3)
C10—C11—C12—C1	41.6 (3)	C11—C27—C28—Cl3	−4.0 (6)
C27—C11—C12—C20	−65.3 (5)	C27—C28—C29—C30	−1.7 (7)
C10—C11—C12—C20	165.8 (3)	Cl3—C28—C29—C30	176.5 (4)
C27—C11—C12—C13	50.2 (5)	C28—C29—C30—C31	2.7 (8)
C10—C11—C12—C13	−78.7 (4)	C28—C29—C30—Cl4	−176.4 (4)
C1—C12—C13—O2	−79.6 (4)	C29—C30—C31—C32	−1.2 (8)
C11—C12—C13—O2	34.1 (5)	Cl4—C30—C31—C32	177.9 (4)
C20—C12—C13—O2	156.4 (3)	C30—C31—C32—C27	−1.5 (8)
C1—C12—C13—C14	155.2 (3)	C28—C27—C32—C31	2.5 (7)
C11—C12—C13—C14	−91.1 (4)	C11—C27—C32—C31	−172.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.82 (5)	1.92 (5)	2.723 (5)	164 (5)
O2—H2···O1^ii	0.83 (5)	1.96 (5)	2.784 (4)	176 (5)

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1/2, −y+3/2, −z+1.