2,4-Dibenzoyl-1,3,5-triphenyl­cyclo­hexan-1-ol dichloro­methane hemisolvate

Zhang, J.-H.; He, Q.-P.; Wang, Y.; Wang, D.-Q.

doi:10.1107/S1600536807056322

2,4-Dibenzoyl-1,3,5-triphenylcyclohexan-1-ol dichloromethane hemisolvate

J.-H. Zhang, Q.-P. He, Y. Wang and D.-Q. Wang

The asymmetric unit of the title compound, C₃₈H₃₂O₃·0.5CH₂Cl₂, which was synthesized by the reaction of benzaldehyde with acetophenone and NaOH under phase-transfer catalysis and solvent-free conditions, contains two independent molecules of 2,4-dibenzoyl-1,3,5-triphenylcyclohexan-1-ol and a disordered dichloromethane molecule. In both independent cyclohexanol molecules, the central six-membered ring adopts a chair conformation and most of the bulky side groups are located in equatorial positions. The hydroxyl groups are involved in weak intramolecular hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056322/cv2326sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056322/cv2326Isup2.hkl Contains datablock I

CCDC reference: 672898

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
Disorder in solvent or counterion
R factor = 0.057
wR factor = 0.175
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C77
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C77'
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.15
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT751_ALERT_4_C Bond    Calc     0.00000, Rep    0.000(6) ......  Senseless su
              O2   -O2      1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     0.00000, Rep    0.000(8) ......  Senseless su
              O5   -O5      1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       0.00 Deg.
              O2   -O2   -C13     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       0.00 Deg.
              O5   -O5   -C51     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       0.00 Deg.
              O2   -C13  -O2      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       0.00 Deg.
              O5   -C51  -O5      1.555   1.555   1.555

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C38.5 H33 Cl1 O3
            Atom count from _chemical_formula_moiety:C38.5 H32 Cl1 O3
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C4     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C5     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C39    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C40    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C41    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C42    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C43    = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        108

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

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

Comment top

In this paper, we present the crystal structure of 2,4-Dibenzoyl-1,3,5-triphenyl-1-cyclohexanol (I) dichloromethane 2:1 solvate, which was synthesized through the condensation and Micheal addition of benzaldehyde with acetophenone under tetrabutyl ammonium bromide and solvent-free conditions.

In the crystal structure, the asymmetric unit contains two independent molecules of (I) (Fig. 1) with normal values of bond lengths and angles corresponding to the published ones (Luo et al., 2006; Huang et al., 2007), and one disordered dichloromethane solvent molecule. The hydroxyl groups in two independent molecules are involved in weak intramolecular hydrogen bonding (Table 1).

Related literature top

The crystal structures of 2,4-dibenzoyl-3,5-bis(4-methoxylphenyl)-1-phenylcyclohexanol and 2,4-dibenzoyl-3,5-bis(2-thienyl)-1-phenylcyclohexanol were reported by Luo & Shan (2006) and Huang & Wang (2007), respectively.

Experimental top

Acetophenone (6.25 mmol), freshly distilled benzaldehyde (3.125 mmol), NaOH (6.25 mmol) and tetrabutyl ammonium bromide (1 mmol) were aggregated with a glass paddle in an open flask. The resulting mixture was washed with water several times to remove NaOH and was recrystallized from ethanol and CH₂Cl₂, affording the title compound as a crystalline solid. Elemental analysis: calculated for C₇₇H₆₆O₆Cl₂: C 79.85, H 5.74%; found: C 79.78, H 5.83%.

Computing details top

Data collection: Bruker SMART (Siemens, 1996); cell refinement: Bruker SAINT (Siemens, 1996); data reduction: Bruker SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: Bruker SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: Bruker SHELXTL (Sheldrick, 1997b).

Figures top

Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering scheme and 20% probabilty displacement ellipsoids. Hydrogen atoms and dichloromethane solvent molecule are omitted for clarity.

2,4-Dibenzoyl-1,3,5-triphenylcyclohexan-1-ol dichloromethane hemisolvate top

Crystal data top

C₃₈H₃₁O₃·0.5CH₂Cl₂	Z = 4
M_r = 579.1	F(000) = 1220
Triclinic, P1	D_x = 1.234 Mg m⁻³
a = 12.452 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.527 (11) Å	Cell parameters from 3197 reflections
c = 20.631 (18) Å	θ = 2.5–22.0°
α = 94.152 (15)°	µ = 0.16 mm⁻¹
β = 97.683 (14)°	T = 298 K
γ = 100.908 (14)°	Block, colourless
V = 3116 (5) Å³	0.44 × 0.39 × 0.33 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	10835 independent reflections
Radiation source: fine-focus sealed tube	5265 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.933, T_max = 0.949	k = −14→14
16393 measured reflections	l = −24→21

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0761P)² + 0.1993P] where P = (F_o² + 2F_c²)/3
10835 reflections	(Δ/σ)_max < 0.001
784 parameters	Δρ_max = 0.40 e Å⁻³
108 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₃₈H₃₁O₃·0.5CH₂Cl₂	γ = 100.908 (14)°
M_r = 579.1	V = 3116 (5) Å³
Triclinic, P1	Z = 4
a = 12.452 (11) Å	Mo Kα radiation
b = 12.527 (11) Å	µ = 0.16 mm⁻¹
c = 20.631 (18) Å	T = 298 K
α = 94.152 (15)°	0.44 × 0.39 × 0.33 mm
β = 97.683 (14)°

Data collection top

Bruker SMART CCD area-detector diffractometer	10835 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5265 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.949	R_int = 0.027
16393 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	108 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.01	Δρ_max = 0.40 e Å⁻³
10835 reflections	Δρ_min = −0.28 e Å⁻³
784 parameters

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	Occ. (<1)
Cl1	0.6656 (2)	0.7680 (2)	0.36319 (11)	0.1137 (8)	0.60
Cl2	0.7072 (2)	0.8105 (4)	0.49918 (13)	0.1926 (15)	0.60
Cl1'	0.6733 (8)	0.7238 (8)	0.4053 (6)	0.320 (5)	0.40
Cl2'	0.6652 (5)	0.9270 (4)	0.4809 (2)	0.189 (2)	0.40
O1	0.36092 (18)	0.40310 (17)	0.36048 (10)	0.0615 (6)
H1	0.3285	0.3744	0.3888	0.092*
O2	0.1561 (2)	0.3367 (2)	0.39103 (12)	0.0739 (7)
O3	0.2578 (2)	0.24637 (19)	0.16499 (11)	0.0682 (7)
O4	0.43540 (19)	0.90376 (19)	0.31106 (12)	0.0751 (7)
H4	0.4821	0.8848	0.2908	0.113*
O5	0.47955 (19)	0.8726 (2)	0.18429 (12)	0.0724 (7)
O6	0.10992 (18)	0.72014 (18)	0.24378 (12)	0.0683 (7)
C1	0.3194 (2)	0.4986 (2)	0.34476 (14)	0.0447 (8)
C2	0.1943 (2)	0.4668 (2)	0.31583 (13)	0.0427 (7)
H2	0.1683	0.5330	0.3041	0.051*
C3	0.1743 (2)	0.3851 (2)	0.25358 (14)	0.0438 (8)
H3	0.1951	0.3176	0.2672	0.053*
C4	0.2475 (2)	0.4258 (2)	0.20236 (14)	0.0441 (8)
H4A	0.2213	0.4871	0.1830	0.053*
C5	0.3712 (2)	0.4628 (2)	0.23160 (14)	0.0469 (8)
H5	0.3975	0.3983	0.2462	0.056*
C6	0.3842 (2)	0.5448 (2)	0.29221 (14)	0.0490 (8)
H6A	0.4619	0.5661	0.3106	0.059*
H6B	0.3591	0.6098	0.2790	0.059*
C7	0.3379 (2)	0.5823 (3)	0.40493 (14)	0.0460 (8)
C8	0.3091 (3)	0.6832 (3)	0.40019 (16)	0.0623 (10)
H8	0.2759	0.6996	0.3600	0.075*
C9	0.3289 (3)	0.7599 (3)	0.45408 (17)	0.0685 (10)
H9	0.3092	0.8274	0.4500	0.082*
C10	0.3779 (3)	0.7368 (3)	0.51393 (17)	0.0658 (10)
H10	0.3919	0.7885	0.5503	0.079*
C11	0.4055 (3)	0.6376 (3)	0.51921 (16)	0.0641 (10)
H11	0.4384	0.6218	0.5596	0.077*
C12	0.3856 (3)	0.5597 (3)	0.46554 (15)	0.0560 (9)
H12	0.4043	0.4919	0.4703	0.067*
C13	0.1275 (3)	0.4156 (3)	0.36602 (15)	0.0490 (8)
C14	0.0314 (3)	0.4560 (3)	0.38562 (15)	0.0507 (8)
C15	−0.0007 (3)	0.5486 (3)	0.36472 (17)	0.0656 (10)
H15	0.0393	0.5895	0.3368	0.079*
C16	−0.0920 (3)	0.5811 (3)	0.3849 (2)	0.0803 (12)
H16	−0.1133	0.6435	0.3702	0.096*
C17	−0.1508 (3)	0.5225 (4)	0.4259 (2)	0.0849 (12)
H17	−0.2115	0.5454	0.4398	0.102*
C18	−0.1206 (3)	0.4297 (4)	0.44666 (18)	0.0773 (12)
H18	−0.1620	0.3889	0.4740	0.093*
C19	−0.0299 (3)	0.3961 (3)	0.42748 (16)	0.0642 (10)
H19	−0.0093	0.3335	0.4424	0.077*
C20	0.0529 (3)	0.3561 (2)	0.22293 (14)	0.0455 (8)
C21	−0.0046 (3)	0.2497 (3)	0.21561 (17)	0.0652 (10)
H21	0.0310	0.1948	0.2298	0.078*
C22	−0.1147 (3)	0.2233 (3)	0.1873 (2)	0.0848 (13)
H22	−0.1523	0.1509	0.1828	0.102*
C23	−0.1684 (3)	0.3017 (4)	0.16631 (18)	0.0781 (12)
H23	−0.2425	0.2834	0.1476	0.094*
C24	−0.1132 (3)	0.4080 (3)	0.17269 (17)	0.0714 (11)
H24	−0.1496	0.4621	0.1581	0.086*
C25	−0.0029 (3)	0.4352 (3)	0.20089 (16)	0.0570 (9)
H25	0.0341	0.5077	0.2051	0.068*
C26	0.2361 (3)	0.3329 (3)	0.14882 (15)	0.0493 (8)
C27	0.2015 (3)	0.3452 (3)	0.07848 (16)	0.0538 (9)
C28	0.1639 (4)	0.4334 (3)	0.05594 (19)	0.0923 (14)
H28	0.1616	0.4920	0.0857	0.111*
C29	0.1288 (5)	0.4374 (4)	−0.0105 (2)	0.1158 (18)
H29	0.1021	0.4976	−0.0246	0.139*
C30	0.1335 (4)	0.3542 (4)	−0.0546 (2)	0.0992 (16)
H30	0.1111	0.3573	−0.0991	0.119*
C31	0.1707 (4)	0.2667 (4)	−0.0337 (2)	0.0949 (15)
H31	0.1737	0.2092	−0.0641	0.114*
C32	0.2046 (3)	0.2609 (3)	0.03230 (19)	0.0770 (11)
H32	0.2297	0.1995	0.0457	0.092*
C33	0.4386 (3)	0.5055 (3)	0.17995 (15)	0.0478 (8)
C34	0.4320 (3)	0.6037 (3)	0.15533 (17)	0.0644 (10)
H34	0.3875	0.6469	0.1726	0.077*
C35	0.4894 (3)	0.6397 (3)	0.10586 (19)	0.0757 (11)
H35	0.4827	0.7058	0.0896	0.091*
C36	0.5563 (3)	0.5777 (4)	0.08089 (19)	0.0773 (12)
H36	0.5949	0.6013	0.0472	0.093*
C37	0.5665 (3)	0.4810 (3)	0.10538 (19)	0.0764 (11)
H37	0.6128	0.4391	0.0888	0.092*
C38	0.5081 (3)	0.4456 (3)	0.15460 (16)	0.0618 (9)
H38	0.5159	0.3798	0.1711	0.074*
C39	0.4095 (3)	1.0040 (3)	0.28854 (15)	0.0497 (8)
C40	0.3593 (2)	0.9856 (2)	0.21476 (14)	0.0435 (7)
H40	0.3385	1.0533	0.2013	0.052*
C41	0.2570 (2)	0.8929 (2)	0.20069 (15)	0.0462 (8)
H41	0.2808	0.8252	0.2113	0.055*
C42	0.1701 (2)	0.9110 (2)	0.24427 (14)	0.0446 (8)
H42	0.1362	0.9713	0.2295	0.054*
C43	0.2189 (2)	0.9378 (3)	0.31802 (15)	0.0504 (8)
H43	0.2420	0.8724	0.3337	0.060*
C44	0.3210 (2)	1.0300 (3)	0.32778 (15)	0.0528 (8)
H44A	0.2992	1.0964	0.3145	0.063*
H44B	0.3516	1.0429	0.3741	0.063*
C45	0.5130 (3)	1.0956 (3)	0.29897 (15)	0.0520 (8)
C46	0.6171 (3)	1.0724 (3)	0.31124 (18)	0.0731 (11)
H46	0.6252	1.0008	0.3156	0.088*
C47	0.7105 (3)	1.1560 (4)	0.3171 (2)	0.0887 (13)
H47	0.7805	1.1395	0.3251	0.106*
C48	0.7006 (4)	1.2612 (4)	0.31141 (18)	0.0806 (12)
H48	0.7633	1.3162	0.3147	0.097*
C49	0.5980 (3)	1.2851 (3)	0.30080 (17)	0.0745 (11)
H49	0.5904	1.3571	0.2977	0.089*
C50	0.5043 (3)	1.2025 (3)	0.29459 (16)	0.0623 (10)
H50	0.4347	1.2199	0.2873	0.075*
C51	0.4469 (3)	0.9577 (3)	0.17487 (16)	0.0530 (9)
C52	0.4938 (3)	1.0293 (3)	0.12746 (15)	0.0496 (8)
C53	0.4558 (3)	1.1216 (3)	0.10951 (17)	0.0645 (10)
H53	0.3984	1.1423	0.1286	0.077*
C54	0.5018 (3)	1.1827 (3)	0.06389 (19)	0.0780 (11)
H54	0.4747	1.2438	0.0519	0.094*
C55	0.5872 (3)	1.1544 (4)	0.03611 (19)	0.0813 (13)
H55	0.6187	1.1965	0.0056	0.098*
C56	0.6260 (3)	1.0641 (4)	0.0533 (2)	0.0830 (13)
H56	0.6843	1.0450	0.0345	0.100*
C57	0.5800 (3)	1.0009 (3)	0.09827 (17)	0.0653 (10)
H57	0.6067	0.9390	0.1091	0.078*
C58	0.2059 (2)	0.8773 (3)	0.12931 (16)	0.0491 (8)
C59	0.1685 (3)	0.9616 (3)	0.09842 (16)	0.0598 (9)
H59	0.1757	1.0289	0.1225	0.072*
C60	0.1211 (3)	0.9480 (4)	0.03316 (19)	0.0761 (11)
H60	0.0984	1.0061	0.0134	0.091*
C61	0.1077 (3)	0.8484 (5)	−0.0023 (2)	0.0906 (14)
H61	0.0738	0.8378	−0.0459	0.109*
C62	0.1442 (4)	0.7648 (4)	0.0267 (2)	0.0916 (14)
H62	0.1361	0.6975	0.0024	0.110*
C63	0.1931 (3)	0.7790 (3)	0.0918 (2)	0.0720 (11)
H63	0.2179	0.7211	0.1106	0.086*
C64	0.0804 (3)	0.8076 (3)	0.23779 (15)	0.0485 (8)
C65	−0.0391 (3)	0.8106 (3)	0.22748 (15)	0.0489 (8)
C66	−0.0807 (3)	0.9029 (3)	0.21618 (19)	0.0741 (11)
H66	−0.0322	0.9683	0.2136	0.089*
C67	−0.1927 (3)	0.9005 (3)	0.2086 (2)	0.0922 (14)
H67	−0.2191	0.9639	0.2016	0.111*
C68	−0.2644 (3)	0.8055 (4)	0.2114 (2)	0.0830 (12)
H68	−0.3401	0.8037	0.2055	0.100*
C69	−0.2262 (3)	0.7127 (3)	0.22272 (18)	0.0731 (11)
H69	−0.2755	0.6478	0.2252	0.088*
C70	−0.1142 (3)	0.7154 (3)	0.23058 (16)	0.0588 (9)
H70	−0.0886	0.6516	0.2382	0.071*
C71	0.1287 (3)	0.9628 (3)	0.35635 (15)	0.0514 (8)
C72	0.0953 (3)	1.0615 (3)	0.35598 (17)	0.0651 (10)
H72	0.1337	1.1175	0.3357	0.078*
C73	0.0060 (3)	1.0784 (4)	0.3852 (2)	0.0820 (12)
H73	−0.0158	1.1453	0.3841	0.098*
C74	−0.0505 (3)	0.9978 (4)	0.4156 (2)	0.0910 (14)
H74	−0.1115	1.0092	0.4346	0.109*
C75	−0.0171 (3)	0.8993 (4)	0.41813 (19)	0.0854 (13)
H75	−0.0545	0.8444	0.4396	0.102*
C76	0.0716 (3)	0.8826 (3)	0.38880 (17)	0.0663 (10)
H76	0.0939	0.8159	0.3907	0.080*
C77	0.6124 (5)	0.8111 (7)	0.4318 (3)	0.172 (3)	0.60
H77A	0.5982	0.8842	0.4284	0.207*	0.60
H77B	0.5433	0.7624	0.4352	0.207*	0.60
C77'	0.6124 (5)	0.8111 (7)	0.4318 (3)	0.172 (3)	0.40
H77C	0.5560	0.7712	0.4541	0.207*	0.40
H77D	0.5730	0.8337	0.3930	0.207*	0.40

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1009 (17)	0.148 (2)	0.0975 (16)	0.0285 (15)	0.0339 (13)	0.0032 (14)
Cl2	0.110 (2)	0.346 (5)	0.0979 (19)	−0.011 (3)	0.0096 (14)	0.027 (3)
Cl1'	0.198 (7)	0.340 (11)	0.414 (13)	0.051 (7)	0.046 (9)	−0.003 (9)
Cl2'	0.222 (5)	0.190 (4)	0.115 (3)	−0.060 (4)	0.064 (3)	−0.051 (3)
O1	0.0713 (16)	0.0643 (15)	0.0539 (14)	0.0289 (13)	0.0042 (11)	0.0072 (11)
O2	0.0840 (19)	0.0666 (17)	0.0784 (17)	0.0199 (14)	0.0186 (13)	0.0305 (14)
O3	0.0891 (19)	0.0502 (15)	0.0669 (16)	0.0242 (13)	0.0103 (13)	−0.0080 (12)
O4	0.0585 (16)	0.0811 (18)	0.0909 (18)	0.0220 (13)	0.0096 (13)	0.0248 (15)
O5	0.0629 (17)	0.0610 (16)	0.103 (2)	0.0278 (13)	0.0258 (13)	0.0051 (14)
O6	0.0562 (15)	0.0432 (14)	0.109 (2)	0.0111 (12)	0.0219 (13)	0.0120 (13)
C1	0.048 (2)	0.0444 (19)	0.0437 (18)	0.0154 (15)	0.0031 (14)	0.0059 (15)
C2	0.0446 (19)	0.0406 (18)	0.0414 (17)	0.0079 (14)	0.0043 (14)	0.0008 (14)
C3	0.0470 (19)	0.0393 (18)	0.0441 (18)	0.0092 (15)	0.0047 (14)	0.0009 (14)
C4	0.0487 (19)	0.0397 (18)	0.0434 (18)	0.0115 (15)	0.0040 (14)	0.0000 (14)
C5	0.046 (2)	0.0470 (19)	0.0495 (19)	0.0147 (15)	0.0076 (15)	0.0016 (15)
C6	0.0427 (19)	0.054 (2)	0.0480 (19)	0.0102 (15)	0.0017 (15)	−0.0023 (16)
C7	0.0394 (19)	0.056 (2)	0.0404 (18)	0.0090 (16)	0.0027 (14)	0.0004 (15)
C8	0.078 (3)	0.058 (2)	0.047 (2)	0.020 (2)	−0.0070 (17)	−0.0056 (18)
C9	0.083 (3)	0.061 (2)	0.057 (2)	0.017 (2)	0.002 (2)	−0.0112 (19)
C10	0.060 (2)	0.077 (3)	0.053 (2)	0.004 (2)	0.0111 (18)	−0.018 (2)
C11	0.060 (2)	0.089 (3)	0.039 (2)	0.013 (2)	0.0027 (16)	0.002 (2)
C12	0.052 (2)	0.072 (2)	0.045 (2)	0.0177 (18)	0.0030 (16)	0.0051 (18)
C13	0.055 (2)	0.046 (2)	0.0426 (18)	0.0047 (17)	0.0022 (15)	0.0049 (16)
C14	0.050 (2)	0.053 (2)	0.0437 (19)	−0.0009 (17)	0.0074 (16)	−0.0043 (16)
C15	0.062 (3)	0.071 (3)	0.070 (2)	0.018 (2)	0.0220 (19)	0.009 (2)
C16	0.076 (3)	0.087 (3)	0.090 (3)	0.029 (2)	0.033 (2)	0.013 (2)
C17	0.066 (3)	0.101 (4)	0.085 (3)	0.009 (3)	0.025 (2)	−0.012 (3)
C18	0.065 (3)	0.092 (3)	0.064 (3)	−0.016 (2)	0.025 (2)	−0.008 (2)
C19	0.063 (2)	0.066 (2)	0.056 (2)	−0.008 (2)	0.0125 (18)	0.0002 (18)
C20	0.050 (2)	0.044 (2)	0.0397 (18)	0.0044 (16)	0.0059 (14)	0.0002 (15)
C21	0.070 (3)	0.048 (2)	0.070 (2)	0.0027 (19)	0.0000 (19)	0.0043 (18)
C22	0.072 (3)	0.067 (3)	0.097 (3)	−0.020 (2)	−0.005 (2)	0.007 (2)
C23	0.053 (2)	0.094 (3)	0.071 (3)	−0.011 (2)	−0.0064 (19)	−0.002 (2)
C24	0.057 (2)	0.079 (3)	0.073 (3)	0.014 (2)	−0.0062 (19)	0.004 (2)
C25	0.051 (2)	0.050 (2)	0.064 (2)	0.0066 (17)	−0.0021 (17)	0.0014 (17)
C26	0.049 (2)	0.044 (2)	0.055 (2)	0.0115 (16)	0.0096 (15)	−0.0030 (17)
C27	0.057 (2)	0.052 (2)	0.047 (2)	−0.0010 (17)	0.0118 (16)	−0.0037 (17)
C28	0.144 (4)	0.075 (3)	0.054 (3)	0.032 (3)	−0.006 (2)	−0.004 (2)
C29	0.190 (6)	0.103 (4)	0.052 (3)	0.041 (4)	−0.008 (3)	0.005 (3)
C30	0.124 (4)	0.109 (4)	0.051 (3)	−0.007 (3)	0.009 (2)	0.002 (3)
C31	0.122 (4)	0.094 (4)	0.056 (3)	−0.008 (3)	0.026 (2)	−0.025 (2)
C32	0.093 (3)	0.073 (3)	0.061 (3)	0.007 (2)	0.020 (2)	−0.013 (2)
C33	0.047 (2)	0.047 (2)	0.0470 (19)	0.0075 (16)	0.0050 (15)	−0.0030 (16)
C34	0.075 (3)	0.057 (2)	0.065 (2)	0.0151 (19)	0.0217 (19)	0.0097 (19)
C35	0.089 (3)	0.064 (3)	0.073 (3)	0.007 (2)	0.015 (2)	0.013 (2)
C36	0.076 (3)	0.079 (3)	0.068 (3)	−0.010 (2)	0.022 (2)	−0.001 (2)
C37	0.074 (3)	0.078 (3)	0.082 (3)	0.015 (2)	0.032 (2)	0.004 (2)
C38	0.066 (2)	0.062 (2)	0.061 (2)	0.0148 (19)	0.0223 (19)	0.0035 (18)
C39	0.0421 (19)	0.052 (2)	0.057 (2)	0.0164 (16)	0.0040 (15)	0.0090 (16)
C40	0.0374 (18)	0.0410 (18)	0.0542 (19)	0.0118 (14)	0.0103 (14)	0.0027 (15)
C41	0.0410 (19)	0.0382 (18)	0.060 (2)	0.0107 (15)	0.0085 (15)	0.0003 (15)
C42	0.0398 (18)	0.0400 (18)	0.055 (2)	0.0113 (14)	0.0078 (14)	0.0027 (15)
C43	0.0434 (19)	0.053 (2)	0.055 (2)	0.0094 (16)	0.0088 (15)	0.0070 (16)
C44	0.045 (2)	0.062 (2)	0.0478 (19)	0.0059 (17)	0.0056 (15)	0.0008 (16)
C45	0.041 (2)	0.063 (2)	0.050 (2)	0.0088 (17)	0.0030 (15)	0.0015 (17)
C46	0.044 (2)	0.088 (3)	0.086 (3)	0.011 (2)	0.0070 (19)	0.002 (2)
C47	0.042 (2)	0.123 (4)	0.097 (3)	0.013 (3)	0.006 (2)	0.001 (3)
C48	0.061 (3)	0.100 (4)	0.067 (3)	−0.011 (3)	0.007 (2)	−0.006 (2)
C49	0.067 (3)	0.076 (3)	0.069 (3)	−0.006 (2)	0.003 (2)	0.001 (2)
C50	0.045 (2)	0.070 (3)	0.066 (2)	0.0018 (19)	0.0025 (17)	0.0046 (19)
C51	0.040 (2)	0.050 (2)	0.066 (2)	0.0099 (17)	0.0045 (16)	−0.0071 (18)
C52	0.0409 (19)	0.048 (2)	0.056 (2)	0.0024 (16)	0.0101 (15)	−0.0096 (17)
C53	0.070 (3)	0.057 (2)	0.067 (2)	0.005 (2)	0.0259 (19)	−0.0013 (19)
C54	0.091 (3)	0.066 (3)	0.077 (3)	0.005 (2)	0.027 (2)	0.006 (2)
C55	0.069 (3)	0.100 (4)	0.064 (3)	−0.014 (3)	0.023 (2)	−0.004 (2)
C56	0.051 (3)	0.117 (4)	0.078 (3)	0.009 (3)	0.023 (2)	−0.009 (3)
C57	0.044 (2)	0.085 (3)	0.065 (2)	0.0114 (19)	0.0137 (18)	−0.008 (2)
C58	0.0400 (19)	0.049 (2)	0.058 (2)	0.0074 (16)	0.0110 (15)	−0.0046 (17)
C59	0.051 (2)	0.070 (2)	0.056 (2)	0.0104 (18)	0.0050 (17)	−0.0013 (19)
C60	0.057 (2)	0.099 (3)	0.065 (3)	0.007 (2)	−0.001 (2)	0.008 (2)
C61	0.060 (3)	0.130 (4)	0.065 (3)	−0.011 (3)	0.004 (2)	−0.012 (3)
C62	0.082 (3)	0.089 (3)	0.088 (4)	−0.007 (3)	0.017 (3)	−0.037 (3)
C63	0.067 (3)	0.062 (2)	0.080 (3)	0.004 (2)	0.013 (2)	−0.021 (2)
C64	0.052 (2)	0.042 (2)	0.054 (2)	0.0128 (17)	0.0129 (15)	0.0032 (16)
C65	0.044 (2)	0.049 (2)	0.0504 (19)	0.0066 (17)	0.0039 (15)	−0.0050 (16)
C66	0.046 (2)	0.054 (2)	0.116 (3)	0.0093 (18)	−0.006 (2)	−0.001 (2)
C67	0.050 (3)	0.072 (3)	0.147 (4)	0.021 (2)	−0.015 (2)	−0.009 (3)
C68	0.042 (2)	0.091 (3)	0.108 (3)	0.013 (2)	−0.004 (2)	−0.013 (3)
C69	0.045 (2)	0.076 (3)	0.088 (3)	−0.006 (2)	0.0056 (19)	−0.003 (2)
C70	0.053 (2)	0.056 (2)	0.064 (2)	0.0072 (18)	0.0071 (17)	0.0012 (17)
C71	0.044 (2)	0.056 (2)	0.052 (2)	0.0070 (17)	0.0064 (16)	0.0016 (17)
C72	0.056 (2)	0.064 (3)	0.076 (3)	0.0132 (19)	0.0170 (19)	−0.002 (2)
C73	0.062 (3)	0.080 (3)	0.103 (3)	0.017 (2)	0.021 (2)	−0.018 (3)
C74	0.064 (3)	0.110 (4)	0.096 (3)	0.007 (3)	0.034 (2)	−0.022 (3)
C75	0.072 (3)	0.101 (4)	0.081 (3)	−0.001 (3)	0.036 (2)	0.003 (3)
C76	0.062 (2)	0.071 (3)	0.065 (2)	0.005 (2)	0.0184 (19)	0.007 (2)
C77	0.113 (5)	0.272 (8)	0.136 (5)	0.037 (5)	0.043 (4)	0.005 (5)
C77'	0.113 (5)	0.272 (8)	0.136 (5)	0.037 (5)	0.043 (4)	0.005 (5)

Geometric parameters (Å, º) top

Cl1—C77	1.736 (7)	C36—C37	1.368 (5)
Cl2—C77	1.700 (7)	C36—H36	0.9300
O1—C1	1.432 (3)	C37—C38	1.377 (5)
O1—H1	0.8200	C37—H37	0.9300
O2—O2	0.000 (6)	C38—H38	0.9300
O2—C13	1.236 (4)	C39—C44	1.521 (4)
O3—C26	1.224 (3)	C39—C45	1.534 (4)
O4—C39	1.446 (4)	C39—C40	1.550 (4)
O4—H4	0.8200	C40—C51	1.526 (4)
O5—O5	0.000 (8)	C40—C41	1.533 (4)
O5—C51	1.230 (4)	C40—H40	0.9800
O6—C64	1.229 (3)	C41—C58	1.507 (4)
C1—C6	1.520 (4)	C41—C42	1.535 (4)
C1—C7	1.529 (4)	C41—H41	0.9800
C1—C2	1.557 (4)	C42—C64	1.527 (4)
C2—C13	1.517 (4)	C42—C43	1.549 (4)
C2—C3	1.545 (4)	C42—H42	0.9800
C2—H2	0.9800	C43—C71	1.524 (4)
C3—C20	1.524 (4)	C43—C44	1.527 (4)
C3—C4	1.538 (4)	C43—H43	0.9800
C3—H3	0.9800	C44—H44A	0.9700
C4—C26	1.518 (4)	C44—H44B	0.9700
C4—C5	1.547 (4)	C45—C50	1.372 (5)
C4—H4A	0.9800	C45—C46	1.377 (5)
C5—C33	1.509 (4)	C46—C47	1.395 (5)
C5—C6	1.531 (4)	C46—H46	0.9300
C5—H5	0.9800	C47—C48	1.359 (5)
C6—H6A	0.9700	C47—H47	0.9300
C6—H6B	0.9700	C48—C49	1.360 (5)
C7—C12	1.383 (4)	C48—H48	0.9300
C7—C8	1.384 (4)	C49—C50	1.390 (5)
C8—C9	1.379 (4)	C49—H49	0.9300
C8—H8	0.9300	C50—H50	0.9300
C9—C10	1.378 (5)	C51—O5	1.230 (4)
C9—H9	0.9300	C51—C52	1.477 (5)
C10—C11	1.358 (5)	C52—C53	1.385 (4)
C10—H10	0.9300	C52—C57	1.388 (4)
C11—C12	1.386 (4)	C53—C54	1.372 (5)
C11—H11	0.9300	C53—H53	0.9300
C12—H12	0.9300	C54—C55	1.364 (5)
C13—O2	1.236 (4)	C54—H54	0.9300
C13—C14	1.477 (5)	C55—C56	1.363 (5)
C14—C15	1.375 (4)	C55—H55	0.9300
C14—C19	1.394 (4)	C56—C57	1.375 (5)
C15—C16	1.381 (5)	C56—H56	0.9300
C15—H15	0.9300	C57—H57	0.9300
C16—C17	1.358 (5)	C58—C63	1.376 (4)
C16—H16	0.9300	C58—C59	1.393 (4)
C17—C18	1.368 (5)	C59—C60	1.381 (5)
C17—H17	0.9300	C59—H59	0.9300
C18—C19	1.373 (5)	C60—C61	1.370 (6)
C18—H18	0.9300	C60—H60	0.9300
C19—H19	0.9300	C61—C62	1.364 (6)
C20—C21	1.376 (4)	C61—H61	0.9300
C20—C25	1.383 (4)	C62—C63	1.383 (6)
C21—C22	1.385 (5)	C62—H62	0.9300
C21—H21	0.9300	C63—H63	0.9300
C22—C23	1.354 (5)	C64—C65	1.482 (4)
C22—H22	0.9300	C65—C66	1.377 (4)
C23—C24	1.366 (5)	C65—C70	1.381 (4)
C23—H23	0.9300	C66—C67	1.377 (5)
C24—C25	1.386 (4)	C66—H66	0.9300
C24—H24	0.9300	C67—C68	1.356 (5)
C25—H25	0.9300	C67—H67	0.9300
C26—C27	1.485 (5)	C68—C69	1.361 (5)
C27—C28	1.366 (5)	C68—H68	0.9300
C27—C32	1.380 (5)	C69—C70	1.376 (5)
C28—C29	1.390 (5)	C69—H69	0.9300
C28—H28	0.9300	C70—H70	0.9300
C29—C30	1.347 (6)	C71—C72	1.376 (4)
C29—H29	0.9300	C71—C76	1.385 (4)
C30—C31	1.346 (6)	C72—C73	1.376 (5)
C30—H30	0.9300	C72—H72	0.9300
C31—C32	1.381 (5)	C73—C74	1.359 (5)
C31—H31	0.9300	C73—H73	0.9300
C32—H32	0.9300	C74—C75	1.377 (6)
C33—C34	1.377 (4)	C74—H74	0.9300
C33—C38	1.378 (4)	C75—C76	1.370 (5)
C34—C35	1.377 (5)	C75—H75	0.9300
C34—H34	0.9300	C76—H76	0.9300
C35—C36	1.365 (5)	C77—H77A	0.9700
C35—H35	0.9300	C77—H77B	0.9700

C1—O1—H1	109.5	O4—C39—C45	111.1 (3)
O2—O2—C13	0 (10)	C44—C39—C45	112.5 (3)
C39—O4—H4	109.5	O4—C39—C40	110.4 (2)
O5—O5—C51	0 (10)	C44—C39—C40	108.2 (2)
O1—C1—C6	105.1 (2)	C45—C39—C40	109.5 (2)
O1—C1—C7	111.3 (2)	C51—C40—C41	109.1 (2)
C6—C1—C7	110.4 (2)	C51—C40—C39	108.7 (2)
O1—C1—C2	110.2 (2)	C41—C40—C39	112.2 (2)
C6—C1—C2	109.2 (2)	C51—C40—H40	109.0
C7—C1—C2	110.5 (2)	C41—C40—H40	109.0
C13—C2—C3	108.6 (2)	C39—C40—H40	109.0
C13—C2—C1	110.7 (2)	C58—C41—C40	112.3 (2)
C3—C2—C1	111.3 (2)	C58—C41—C42	110.0 (2)
C13—C2—H2	108.7	C40—C41—C42	111.5 (2)
C3—C2—H2	108.7	C58—C41—H41	107.6
C1—C2—H2	108.7	C40—C41—H41	107.6
C20—C3—C4	110.7 (2)	C42—C41—H41	107.6
C20—C3—C2	112.2 (2)	C64—C42—C41	109.4 (2)
C4—C3—C2	112.2 (2)	C64—C42—C43	107.6 (2)
C20—C3—H3	107.1	C41—C42—C43	113.0 (2)
C4—C3—H3	107.1	C64—C42—H42	108.9
C2—C3—H3	107.1	C41—C42—H42	108.9
C26—C4—C3	108.1 (2)	C43—C42—H42	108.9
C26—C4—C5	108.5 (2)	C71—C43—C44	113.1 (3)
C3—C4—C5	113.0 (2)	C71—C43—C42	109.0 (2)
C26—C4—H4A	109.0	C44—C43—C42	111.0 (2)
C3—C4—H4A	109.0	C71—C43—H43	107.9
C5—C4—H4A	109.0	C44—C43—H43	107.9
C33—C5—C6	113.3 (3)	C42—C43—H43	107.9
C33—C5—C4	110.9 (2)	C39—C44—C43	112.3 (3)
C6—C5—C4	110.0 (2)	C39—C44—H44A	109.2
C33—C5—H5	107.5	C43—C44—H44A	109.2
C6—C5—H5	107.5	C39—C44—H44B	109.2
C4—C5—H5	107.5	C43—C44—H44B	109.2
C1—C6—C5	112.4 (3)	H44A—C44—H44B	107.9
C1—C6—H6A	109.1	C50—C45—C46	118.2 (3)
C5—C6—H6A	109.1	C50—C45—C39	120.9 (3)
C1—C6—H6B	109.1	C46—C45—C39	120.8 (3)
C5—C6—H6B	109.1	C45—C46—C47	120.1 (4)
H6A—C6—H6B	107.8	C45—C46—H46	119.9
C12—C7—C8	118.2 (3)	C47—C46—H46	119.9
C12—C7—C1	120.7 (3)	C48—C47—C46	120.9 (4)
C8—C7—C1	121.1 (3)	C48—C47—H47	119.5
C9—C8—C7	121.1 (3)	C46—C47—H47	119.5
C9—C8—H8	119.5	C47—C48—C49	119.3 (4)
C7—C8—H8	119.5	C47—C48—H48	120.4
C10—C9—C8	120.1 (4)	C49—C48—H48	120.4
C10—C9—H9	120.0	C48—C49—C50	120.3 (4)
C8—C9—H9	120.0	C48—C49—H49	119.9
C11—C10—C9	119.3 (3)	C50—C49—H49	119.9
C11—C10—H10	120.4	C45—C50—C49	121.1 (4)
C9—C10—H10	120.4	C45—C50—H50	119.4
C10—C11—C12	121.2 (3)	C49—C50—H50	119.4
C10—C11—H11	119.4	O5—C51—O5	0.0 (2)
C12—C11—H11	119.4	O5—C51—C52	120.0 (3)
C7—C12—C11	120.2 (3)	O5—C51—C52	120.0 (3)
C7—C12—H12	119.9	O5—C51—C40	117.3 (3)
C11—C12—H12	119.9	O5—C51—C40	117.3 (3)
O2—C13—O2	0.0 (2)	C52—C51—C40	122.7 (3)
O2—C13—C14	119.7 (3)	C53—C52—C57	118.1 (3)
O2—C13—C14	119.7 (3)	C53—C52—C51	124.1 (3)
O2—C13—C2	117.5 (3)	C57—C52—C51	117.8 (3)
O2—C13—C2	117.5 (3)	C54—C53—C52	120.8 (4)
C14—C13—C2	122.8 (3)	C54—C53—H53	119.6
C15—C14—C19	118.7 (3)	C52—C53—H53	119.6
C15—C14—C13	123.7 (3)	C55—C54—C53	120.4 (4)
C19—C14—C13	117.6 (3)	C55—C54—H54	119.8
C14—C15—C16	120.4 (4)	C53—C54—H54	119.8
C14—C15—H15	119.8	C56—C55—C54	119.6 (4)
C16—C15—H15	119.8	C56—C55—H55	120.2
C17—C16—C15	120.5 (4)	C54—C55—H55	120.2
C17—C16—H16	119.8	C55—C56—C57	120.9 (4)
C15—C16—H16	119.8	C55—C56—H56	119.6
C16—C17—C18	119.9 (4)	C57—C56—H56	119.6
C16—C17—H17	120.1	C56—C57—C52	120.2 (4)
C18—C17—H17	120.1	C56—C57—H57	119.9
C17—C18—C19	120.6 (4)	C52—C57—H57	119.9
C17—C18—H18	119.7	C63—C58—C59	116.9 (3)
C19—C18—H18	119.7	C63—C58—C41	121.7 (3)
C18—C19—C14	119.9 (4)	C59—C58—C41	121.4 (3)
C18—C19—H19	120.1	C60—C59—C58	121.9 (3)
C14—C19—H19	120.1	C60—C59—H59	119.0
C21—C20—C25	117.8 (3)	C58—C59—H59	119.0
C21—C20—C3	120.9 (3)	C61—C60—C59	119.5 (4)
C25—C20—C3	121.4 (3)	C61—C60—H60	120.2
C20—C21—C22	120.8 (3)	C59—C60—H60	120.2
C20—C21—H21	119.6	C62—C61—C60	119.6 (4)
C22—C21—H21	119.6	C62—C61—H61	120.2
C23—C22—C21	120.7 (4)	C60—C61—H61	120.2
C23—C22—H22	119.6	C61—C62—C63	120.7 (4)
C21—C22—H22	119.6	C61—C62—H62	119.6
C22—C23—C24	119.7 (4)	C63—C62—H62	119.6
C22—C23—H23	120.2	C58—C63—C62	121.2 (4)
C24—C23—H23	120.2	C58—C63—H63	119.4
C23—C24—C25	120.0 (4)	C62—C63—H63	119.4
C23—C24—H24	120.0	O6—C64—C65	119.9 (3)
C25—C24—H24	120.0	O6—C64—C42	117.9 (3)
C20—C25—C24	121.0 (3)	C65—C64—C42	122.2 (3)
C20—C25—H25	119.5	C66—C65—C70	117.3 (3)
C24—C25—H25	119.5	C66—C65—C64	124.3 (3)
O3—C26—C27	120.0 (3)	C70—C65—C64	118.4 (3)
O3—C26—C4	118.0 (3)	C65—C66—C67	121.3 (4)
C27—C26—C4	121.9 (3)	C65—C66—H66	119.4
C28—C27—C32	117.1 (3)	C67—C66—H66	119.4
C28—C27—C26	124.7 (3)	C68—C67—C66	120.0 (4)
C32—C27—C26	118.2 (3)	C68—C67—H67	120.0
C27—C28—C29	121.5 (4)	C66—C67—H67	120.0
C27—C28—H28	119.3	C67—C68—C69	120.3 (4)
C29—C28—H28	119.3	C67—C68—H68	119.8
C30—C29—C28	120.1 (5)	C69—C68—H68	119.8
C30—C29—H29	119.9	C68—C69—C70	119.6 (4)
C28—C29—H29	119.9	C68—C69—H69	120.2
C31—C30—C29	119.6 (4)	C70—C69—H69	120.2
C31—C30—H30	120.2	C69—C70—C65	121.5 (3)
C29—C30—H30	120.2	C69—C70—H70	119.3
C30—C31—C32	121.0 (4)	C65—C70—H70	119.3
C30—C31—H31	119.5	C72—C71—C76	117.8 (3)
C32—C31—H31	119.5	C72—C71—C43	121.9 (3)
C27—C32—C31	120.7 (4)	C76—C71—C43	120.1 (3)
C27—C32—H32	119.7	C73—C72—C71	120.9 (4)
C31—C32—H32	119.7	C73—C72—H72	119.5
C34—C33—C38	117.3 (3)	C71—C72—H72	119.5
C34—C33—C5	122.1 (3)	C74—C73—C72	120.4 (4)
C38—C33—C5	120.6 (3)	C74—C73—H73	119.8
C35—C34—C33	121.8 (4)	C72—C73—H73	119.8
C35—C34—H34	119.1	C73—C74—C75	119.8 (4)
C33—C34—H34	119.1	C73—C74—H74	120.1
C36—C35—C34	119.6 (4)	C75—C74—H74	120.1
C36—C35—H35	120.2	C76—C75—C74	119.6 (4)
C34—C35—H35	120.2	C76—C75—H75	120.2
C35—C36—C37	120.0 (4)	C74—C75—H75	120.2
C35—C36—H36	120.0	C75—C76—C71	121.4 (4)
C37—C36—H36	120.0	C75—C76—H76	119.3
C36—C37—C38	119.9 (4)	C71—C76—H76	119.3
C36—C37—H37	120.0	Cl2—C77—Cl1	107.9 (4)
C38—C37—H37	120.0	Cl2—C77—H77A	110.1
C37—C38—C33	121.4 (4)	Cl1—C77—H77A	110.1
C37—C38—H38	119.3	Cl2—C77—H77B	110.1
C33—C38—H38	119.3	Cl1—C77—H77B	110.1
O4—C39—C44	105.1 (3)	H77A—C77—H77B	108.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.12	2.701 (4)	128
O4—H4···O5	0.82	2.19	2.759 (4)	127

Experimental details

Crystal data
Chemical formula	C₃₈H₃₁O₃·0.5CH₂Cl₂
M_r	579.1
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	12.452 (11), 12.527 (11), 20.631 (18)
α, β, γ (°)	94.152 (15), 97.683 (14), 100.908 (14)
V (Å³)	3116 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.44 × 0.39 × 0.33

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.933, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	16393, 10835, 5265
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.175, 1.01
No. of reflections	10835
No. of parameters	784
No. of restraints	108
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.28

Computer programs: Bruker SMART (Siemens, 1996), Bruker SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), Bruker SHELXTL (Sheldrick, 1997b).