2,4-Dibenzoyl-3,5-bis­(4-methoxy­lphen­yl)-1-phenyl­cyclo­hexa­nol

The title compound, C₄₀H₃₆O₅, was synthesized from p-anisaldehyde and acetophenone. The central six-membered ring adopts a chair conformation and most of the bulky side groups are located in equatorial positions. The hydroxyl group is involved in weak intra- and inter­molecular hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.110
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.71 Ratio

Author Response: The thermal vibration of the molecule is disorder.

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.61 Ratio

Author Response: The thermal vibration of the molecule is disorder.

PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C11

Author Response: The thermal vibration of the molecule is disorder.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?

Author Response: the difference was caused by the vibration disorder probably.

PLAT230_ALERT_2_C Hirshfeld Test Diff for    C19    -   C24     ..       5.42 su

Author Response: The parameter of the two adjacent atoms was effected by the vibration disorder.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29

Author Response: The thermal vibration of the molecule is disorder.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7

Author Response: The thermal vibration of the molecule is disorder.

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   7 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
   5 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: Bruker SMART (Bruker 1997); cell refinement: Bruker SAINT (Bruker 1997); data reduction: Bruker SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL (Bruker 1997); software used to prepare material for publication: Bruker SHELXTL (Bruker 1997).

2,4-dibenzoyl-3,5-bis(4-methoxylphenyl)-1-phenylcyclohexanol

Crystal data

C40H36O5	Z = 2
Mr = 596.69	F(000) = 630
Triclinic, P1	Dx = 1.257 Mg m^−3
Hall symbol: -P 1	Melting point: 373(375) K
a = 9.941 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.551 (2) Å	Cell parameters from 2907 reflections
c = 15.240 (3) Å	θ = 2.5–25.7°
α = 68.271 (3)°	µ = 0.08 mm^−1
β = 89.203 (3)°	T = 273 K
γ = 76.337 (3)°	Plate, white
V = 1574.4 (5) Å^3	0.64 × 0.26 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	6997 independent reflections
Radiation source: fine-focus sealed tube	4245 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan SADABS Sheldrick, 1996)	h = −12→12
Tmin = 0.950, Tmax = 0.992	k = −11→15
10262 measured reflections	l = −15→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.047P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max = 0.001
6997 reflections	Δρmax = 0.27 e Å^−3
535 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0115 (13)

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
C1	−0.34866 (16)	0.09460 (15)	0.46923 (12)	0.0481 (4)
C2	−0.24385 (16)	0.05860 (15)	0.41606 (11)	0.0471 (4)
C3	−0.26564 (14)	0.09240 (13)	0.31941 (10)	0.0422 (4)
C4	−0.39734 (16)	0.16361 (15)	0.27701 (11)	0.0494 (4)
C5	−0.50255 (17)	0.20094 (15)	0.32809 (11)	0.0511 (4)
C6	−0.47772 (15)	0.16676 (13)	0.42486 (11)	0.0451 (4)
C7	0.14996 (16)	−0.23763 (14)	0.28321 (11)	0.0470 (4)
C8	0.22605 (18)	−0.26549 (16)	0.36629 (14)	0.0682 (5)
H36	0.2104	−0.2054	0.3948	0.082*
C9	0.3256 (2)	−0.38070 (19)	0.40893 (18)	0.0816 (6)
C10	0.3517 (3)	−0.4679 (2)	0.3674 (2)	0.1000 (8)
C11	0.2788 (3)	−0.4425 (2)	0.2863 (2)	0.1277 (11)
H10	0.2969	−0.5023	0.2575	0.153*
C12	0.1768 (3)	−0.32873 (18)	0.24420 (15)	0.0940 (7)
H11	0.1263	−0.3146	0.1887	0.113*
C13	0.10295 (14)	0.23844 (13)	0.09861 (10)	0.0398 (3)
C14	0.07281 (15)	0.31218 (14)	0.00253 (10)	0.0428 (4)
C15	0.13144 (16)	0.41279 (15)	−0.04352 (11)	0.0473 (4)
C16	0.22363 (15)	0.44304 (13)	0.00617 (11)	0.0443 (4)
C17	0.25936 (17)	0.36950 (15)	0.10036 (12)	0.0523 (4)
C18	0.19959 (17)	0.26783 (16)	0.14567 (12)	0.0523 (4)
C19	0.36173 (14)	−0.07958 (13)	0.12305 (10)	0.0402 (3)
C20	0.44598 (16)	−0.06538 (17)	0.18799 (12)	0.0520 (4)
C21	0.58903 (17)	−0.10766 (19)	0.19127 (13)	0.0622 (5)
C22	0.64896 (18)	−0.16648 (17)	0.13176 (14)	0.0623 (5)
C23	0.56628 (18)	−0.18117 (18)	0.06677 (15)	0.0640 (5)
C24	0.42423 (17)	−0.13686 (16)	0.06194 (13)	0.0544 (4)
C25	−0.05241 (18)	0.29738 (15)	0.32414 (11)	0.0534 (4)
C26	−0.1822 (2)	0.38123 (16)	0.29175 (13)	0.0644 (5)
H24	−0.2419	0.3657	0.2534	0.077*
C27	−0.2239 (3)	0.4878 (2)	0.31585 (19)	0.0885 (7)
C28	−0.1349 (4)	0.5128 (3)	0.3694 (2)	0.1263 (11)
C29	−0.0040 (4)	0.4338 (3)	0.4004 (3)	0.1392 (12)
C30	0.0369 (3)	0.3239 (3)	0.37931 (19)	0.0963 (7)
C31	−0.07079 (14)	0.16476 (14)	0.21980 (10)	0.0410 (3)
C32	0.02788 (14)	0.13392 (13)	0.14757 (10)	0.0395 (3)
C33	0.12590 (14)	−0.00222 (13)	0.18932 (10)	0.0385 (3)
C34	0.04486 (14)	−0.10833 (13)	0.23436 (10)	0.0413 (3)
C35	−0.05336 (16)	−0.07336 (15)	0.30451 (11)	0.0450 (4)
C36	−0.15285 (14)	0.05939 (14)	0.25821 (11)	0.0421 (4)
C37	0.20863 (14)	−0.03208 (13)	0.11231 (10)	0.0415 (3)
C38	0.00019 (16)	0.18020 (14)	0.30123 (10)	0.0450 (4)
C39	−0.5734 (2)	0.1784 (2)	0.56726 (14)	0.0658 (5)
C40	0.3335 (3)	0.6054 (2)	0.00703 (18)	0.0727 (6)
H1	−0.3344 (16)	0.0689 (14)	0.5348 (12)	0.062 (5)*
H2	−0.1571 (16)	0.0071 (13)	0.4505 (10)	0.047 (4)*
H3	−0.4157 (14)	0.1865 (13)	0.2100 (11)	0.050 (4)*
H4	−0.5963 (17)	0.2498 (15)	0.2974 (11)	0.064 (5)*
H5	−0.5450 (19)	0.084 (2)	0.6028 (14)	0.087 (6)*
H7	−0.499 (2)	0.2105 (19)	0.5812 (14)	0.097 (7)*
H8	−0.1067 (15)	−0.1408 (14)	0.3262 (10)	0.057 (4)*
H9	0.376 (2)	−0.394 (2)	0.4706 (17)	0.117 (8)*
H12	−0.022 (2)	−0.081 (2)	0.1088 (15)	0.100 (8)*
H13	0.0076 (15)	0.2913 (13)	−0.0317 (10)	0.047 (4)*
H14	0.1060 (16)	0.4624 (15)	−0.1075 (12)	0.062 (5)*
H15	0.3243 (17)	0.3866 (15)	0.1367 (11)	0.063 (5)*
H16	0.2272 (17)	0.2211 (15)	0.2099 (12)	0.066 (5)*
H17	0.360 (2)	0.679 (2)	−0.0396 (15)	0.103 (7)*
H18	0.271 (2)	0.6265 (18)	0.0529 (15)	0.096 (7)*
H19	0.421 (2)	0.5467 (19)	0.0500 (15)	0.097 (7)*
H20	0.134 (3)	0.260 (2)	0.4022 (16)	0.121 (8)*
H21	0.068 (3)	0.447 (3)	0.438 (2)	0.160 (12)*
H22	−0.167 (3)	0.593 (3)	0.3831 (18)	0.147 (10)*
H23	−0.313 (2)	0.5380 (19)	0.2930 (14)	0.093 (7)*
H25	0.4029 (16)	−0.0224 (15)	0.2306 (11)	0.064 (5)*
H26	0.6471 (19)	−0.0989 (17)	0.2354 (13)	0.082 (6)*
H27	0.7487 (17)	−0.1939 (14)	0.1334 (11)	0.062 (5)*
H28	0.6064 (18)	−0.2190 (16)	0.0212 (12)	0.078 (6)*
H29	0.3587 (16)	−0.1393 (14)	0.0149 (11)	0.062 (5)*
H30	−0.0338 (13)	0.1311 (11)	0.0982 (9)	0.033 (3)*
H31	−0.1376 (14)	0.2451 (13)	0.1849 (9)	0.039 (4)*
H32	−0.2011 (14)	0.0618 (12)	0.2002 (10)	0.039 (4)*
H33	0.424 (3)	−0.545 (3)	0.3968 (18)	0.135 (9)*
H34	0.1895 (12)	−0.0070 (11)	0.2389 (9)	0.028 (3)*
H35	0.0038 (15)	−0.0795 (13)	0.3628 (11)	0.055 (4)*
H6	−0.671 (2)	0.2189 (18)	0.5834 (14)	0.096 (6)*
O1	−0.04260 (11)	−0.11594 (11)	0.16456 (9)	0.0562 (3)
O2	0.10076 (11)	0.09778 (10)	0.34853 (7)	0.0578 (3)
O3	−0.58971 (11)	0.20904 (10)	0.46834 (8)	0.0616 (3)
O4	0.27689 (12)	0.54609 (10)	−0.04458 (8)	0.0614 (3)
O5	0.14474 (11)	−0.02025 (11)	0.04003 (8)	0.0610 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0511 (10)	0.0533 (9)	0.0363 (9)	−0.0151 (8)	0.0031 (7)	−0.0114 (7)
C2	0.0381 (8)	0.0520 (9)	0.0423 (9)	−0.0079 (7)	−0.0014 (7)	−0.0098 (7)
C3	0.0376 (8)	0.0447 (8)	0.0393 (8)	−0.0117 (7)	0.0037 (6)	−0.0093 (7)
C4	0.0457 (9)	0.0551 (9)	0.0357 (9)	−0.0059 (7)	−0.0004 (7)	−0.0080 (7)
C5	0.0402 (9)	0.0535 (9)	0.0469 (10)	−0.0015 (7)	−0.0005 (7)	−0.0107 (8)
C6	0.0441 (9)	0.0420 (8)	0.0454 (9)	−0.0106 (7)	0.0095 (7)	−0.0126 (7)
C7	0.0509 (9)	0.0399 (8)	0.0504 (10)	−0.0159 (7)	0.0098 (8)	−0.0146 (7)
C8	0.0634 (11)	0.0520 (10)	0.0831 (14)	−0.0036 (9)	−0.0173 (10)	−0.0243 (10)
C9	0.0708 (13)	0.0563 (12)	0.0968 (18)	−0.0041 (10)	−0.0202 (12)	−0.0116 (12)
C10	0.107 (2)	0.0512 (13)	0.110 (2)	0.0086 (13)	0.0059 (16)	−0.0125 (14)
C11	0.190 (3)	0.0620 (14)	0.112 (2)	0.0266 (17)	−0.020 (2)	−0.0453 (15)
C12	0.146 (2)	0.0575 (12)	0.0695 (14)	0.0022 (13)	−0.0113 (14)	−0.0293 (11)
C13	0.0356 (8)	0.0418 (8)	0.0371 (8)	−0.0081 (6)	0.0028 (6)	−0.0105 (7)
C14	0.0414 (8)	0.0481 (9)	0.0366 (8)	−0.0105 (7)	0.0011 (7)	−0.0137 (7)
C15	0.0510 (9)	0.0481 (9)	0.0340 (9)	−0.0098 (7)	0.0030 (7)	−0.0071 (7)
C16	0.0448 (8)	0.0385 (8)	0.0446 (9)	−0.0104 (7)	0.0092 (7)	−0.0104 (7)
C17	0.0562 (10)	0.0561 (10)	0.0443 (10)	−0.0239 (8)	−0.0014 (8)	−0.0122 (8)
C18	0.0560 (10)	0.0568 (10)	0.0382 (9)	−0.0234 (8)	−0.0047 (8)	−0.0051 (8)
C19	0.0374 (8)	0.0418 (8)	0.0410 (8)	−0.0125 (6)	0.0050 (6)	−0.0136 (7)
C20	0.0399 (9)	0.0713 (11)	0.0498 (10)	−0.0146 (8)	0.0040 (7)	−0.0281 (9)
C21	0.0414 (10)	0.0877 (13)	0.0602 (12)	−0.0190 (9)	0.0001 (8)	−0.0288 (10)
C22	0.0370 (9)	0.0712 (12)	0.0737 (13)	−0.0082 (9)	0.0082 (9)	−0.0250 (10)
C23	0.0505 (11)	0.0697 (12)	0.0805 (14)	−0.0089 (9)	0.0128 (10)	−0.0420 (11)
C24	0.0471 (10)	0.0602 (10)	0.0640 (11)	−0.0136 (8)	0.0029 (8)	−0.0324 (9)
C25	0.0614 (11)	0.0525 (9)	0.0486 (10)	−0.0173 (8)	0.0114 (8)	−0.0198 (8)
C26	0.0730 (12)	0.0537 (10)	0.0622 (12)	−0.0111 (9)	0.0134 (10)	−0.0201 (9)
C27	0.0984 (19)	0.0675 (14)	0.0920 (18)	−0.0023 (14)	0.0200 (15)	−0.0332 (13)
C28	0.144 (3)	0.107 (2)	0.155 (3)	−0.011 (2)	0.013 (2)	−0.092 (2)
C29	0.137 (3)	0.149 (3)	0.180 (3)	−0.021 (2)	−0.007 (2)	−0.125 (3)
C30	0.0937 (17)	0.1073 (18)	0.113 (2)	−0.0157 (15)	−0.0022 (15)	−0.0756 (16)
C31	0.0367 (8)	0.0392 (8)	0.0372 (8)	−0.0051 (7)	0.0001 (6)	−0.0058 (7)
C32	0.0345 (7)	0.0459 (8)	0.0332 (8)	−0.0103 (6)	−0.0020 (6)	−0.0090 (7)
C33	0.0341 (7)	0.0436 (8)	0.0348 (8)	−0.0104 (6)	−0.0010 (6)	−0.0109 (7)
C34	0.0383 (8)	0.0464 (8)	0.0405 (8)	−0.0147 (7)	0.0018 (6)	−0.0151 (7)
C35	0.0421 (9)	0.0450 (9)	0.0434 (9)	−0.0132 (7)	0.0060 (7)	−0.0105 (7)
C36	0.0366 (8)	0.0477 (8)	0.0370 (8)	−0.0105 (7)	0.0015 (7)	−0.0104 (7)
C37	0.0400 (8)	0.0455 (8)	0.0381 (8)	−0.0143 (7)	0.0013 (7)	−0.0125 (7)
C38	0.0448 (9)	0.0474 (9)	0.0384 (8)	−0.0149 (7)	0.0054 (7)	−0.0092 (7)
C39	0.0749 (14)	0.0721 (14)	0.0568 (12)	−0.0236 (12)	0.0207 (10)	−0.0289 (11)
C40	0.0885 (16)	0.0647 (13)	0.0732 (14)	−0.0403 (13)	0.0128 (13)	−0.0228 (12)
O1	0.0517 (7)	0.0737 (8)	0.0506 (8)	−0.0291 (6)	0.0007 (6)	−0.0236 (6)
O2	0.0564 (7)	0.0594 (7)	0.0487 (7)	−0.0049 (6)	−0.0118 (6)	−0.0157 (6)
O3	0.0589 (7)	0.0629 (7)	0.0543 (7)	−0.0044 (6)	0.0146 (6)	−0.0191 (6)
O4	0.0772 (8)	0.0522 (6)	0.0535 (7)	−0.0315 (6)	0.0086 (6)	−0.0092 (6)
O5	0.0449 (6)	0.0958 (9)	0.0462 (7)	−0.0157 (6)	−0.0014 (5)	−0.0321 (6)

Geometric parameters (Å, º)

C1—C6	1.378 (2)	C22—C23	1.378 (3)
C1—C2	1.392 (2)	C22—H27	0.967 (16)
C1—H1	0.934 (16)	C23—C24	1.377 (2)
C2—C3	1.383 (2)	C23—H28	0.984 (18)
C2—H2	0.955 (15)	C24—H29	0.987 (16)
C3—C4	1.389 (2)	C25—C26	1.385 (2)
C3—C36	1.5180 (19)	C25—C30	1.389 (3)
C4—C5	1.378 (2)	C25—C38	1.496 (2)
C4—H3	0.966 (15)	C26—C27	1.383 (3)
C5—C6	1.388 (2)	C26—H24	0.9300
C5—H4	0.987 (17)	C27—C28	1.359 (4)
C6—O3	1.3706 (17)	C27—H23	0.92 (2)
C7—C12	1.364 (2)	C28—C29	1.374 (4)
C7—C8	1.374 (2)	C28—H22	1.01 (3)
C7—C34	1.529 (2)	C29—C30	1.390 (3)
C8—C9	1.389 (2)	C29—H21	1.00 (3)
C8—H36	0.9300	C30—H20	1.04 (2)
C9—C10	1.352 (3)	C31—C38	1.522 (2)
C9—H9	1.01 (2)	C31—C32	1.548 (2)
C10—C11	1.340 (4)	C31—C36	1.555 (2)
C10—H33	0.96 (3)	C31—H31	0.970 (14)
C11—C12	1.390 (3)	C32—C33	1.5427 (19)
C11—H10	0.9300	C32—H30	0.992 (13)
C12—H11	0.9300	C33—C37	1.520 (2)
C13—C18	1.381 (2)	C33—C34	1.5656 (19)
C13—C14	1.3883 (19)	C33—H34	0.968 (13)
C13—C32	1.5214 (19)	C34—O1	1.4233 (17)
C14—C15	1.374 (2)	C34—C35	1.538 (2)
C14—H13	0.963 (15)	C35—C36	1.526 (2)
C15—C16	1.379 (2)	C35—H8	0.998 (15)
C15—H14	0.931 (16)	C35—H35	1.031 (16)
C16—C17	1.370 (2)	C36—H32	1.000 (14)
C16—O4	1.3785 (17)	C37—O5	1.2256 (17)
C17—C18	1.388 (2)	C38—O2	1.2195 (17)
C17—H15	0.956 (16)	C39—O3	1.417 (2)
C18—H16	0.933 (17)	C39—H5	0.99 (2)
C19—C20	1.384 (2)	C39—H7	0.96 (2)
C19—C24	1.392 (2)	C39—H6	1.04 (2)
C19—C37	1.4802 (19)	C40—O4	1.413 (2)
C20—C21	1.385 (2)	C40—H17	0.98 (2)
C20—H25	0.992 (17)	C40—H18	0.99 (2)
C21—C22	1.375 (2)	C40—H19	1.02 (2)
C21—H26	0.940 (19)	O1—H12	0.84 (2)
C6—C1—C2	119.53 (15)	C30—C25—C38	117.18 (17)
C6—C1—H1	119.1 (10)	C27—C26—C25	120.7 (2)
C2—C1—H1	121.4 (10)	C27—C26—H24	119.6
C3—C2—C1	121.80 (15)	C25—C26—H24	119.6
C3—C2—H2	122.1 (8)	C28—C27—C26	119.6 (3)
C1—C2—H2	116.0 (8)	C28—C27—H23	124.5 (14)
C2—C3—C4	117.29 (14)	C26—C27—H23	115.8 (14)
C2—C3—C36	123.49 (13)	C27—C28—C29	121.2 (3)
C4—C3—C36	119.19 (13)	C27—C28—H22	117.6 (16)
C5—C4—C3	121.96 (15)	C29—C28—H22	121.2 (16)
C5—C4—H3	119.3 (9)	C28—C29—C30	119.5 (3)
C3—C4—H3	118.8 (9)	C28—C29—H21	125.7 (17)
C4—C5—C6	119.64 (15)	C30—C29—H21	114.8 (17)
C4—C5—H4	121.1 (9)	C25—C30—C29	120.0 (3)
C6—C5—H4	119.2 (9)	C25—C30—H20	117.0 (13)
O3—C6—C1	125.64 (14)	C29—C30—H20	123.0 (13)
O3—C6—C5	114.59 (13)	C38—C31—C32	114.74 (12)
C1—C6—C5	119.77 (14)	C38—C31—C36	110.58 (12)
C12—C7—C8	116.81 (16)	C32—C31—C36	109.03 (12)
C12—C7—C34	121.42 (16)	C38—C31—H31	108.2 (8)
C8—C7—C34	121.72 (14)	C32—C31—H31	106.7 (8)
C7—C8—C9	121.92 (19)	C36—C31—H31	107.3 (8)
C7—C8—H36	119.0	C13—C32—C33	113.34 (11)
C9—C8—H36	119.0	C13—C32—C31	113.12 (12)
C10—C9—C8	119.8 (2)	C33—C32—C31	112.66 (11)
C10—C9—H9	123.4 (13)	C13—C32—H30	107.1 (7)
C8—C9—H9	116.8 (13)	C33—C32—H30	104.8 (7)
C11—C10—C9	119.2 (2)	C31—C32—H30	104.9 (7)
C11—C10—H33	122.7 (16)	C37—C33—C32	110.08 (11)
C9—C10—H33	118.1 (16)	C37—C33—C34	108.40 (11)
C10—C11—C12	121.4 (2)	C32—C33—C34	112.14 (11)
C10—C11—H10	119.3	C37—C33—H34	109.2 (7)
C12—C11—H10	119.3	C32—C33—H34	109.5 (7)
C7—C12—C11	120.8 (2)	C34—C33—H34	107.5 (7)
C7—C12—H11	119.6	O1—C34—C7	110.01 (12)
C11—C12—H11	119.6	O1—C34—C35	105.33 (12)
C18—C13—C14	116.67 (14)	C7—C34—C35	111.39 (12)
C18—C13—C32	123.18 (13)	O1—C34—C33	111.34 (11)
C14—C13—C32	120.12 (13)	C7—C34—C33	108.66 (11)
C15—C14—C13	122.24 (15)	C35—C34—C33	110.10 (12)
C15—C14—H13	120.0 (8)	C36—C35—C34	112.00 (12)
C13—C14—H13	117.8 (8)	C36—C35—H8	110.1 (9)
C14—C15—C16	119.76 (15)	C34—C35—H8	105.7 (8)
C14—C15—H14	119.9 (10)	C36—C35—H35	111.2 (8)
C16—C15—H14	120.2 (10)	C34—C35—H35	109.8 (8)
C17—C16—O4	124.05 (15)	H8—C35—H35	107.9 (12)
C17—C16—C15	119.50 (14)	C3—C36—C35	114.69 (12)
O4—C16—C15	116.43 (14)	C3—C36—C31	112.11 (12)
C16—C17—C18	119.94 (16)	C35—C36—C31	110.57 (12)
C16—C17—H15	121.8 (10)	C3—C36—H32	106.6 (7)
C18—C17—H15	118.2 (10)	C35—C36—H32	107.9 (7)
C13—C18—C17	121.79 (16)	C31—C36—H32	104.3 (7)
C13—C18—H16	121.8 (10)	O5—C37—C19	119.13 (13)
C17—C18—H16	116.4 (10)	O5—C37—C33	118.22 (13)
C20—C19—C24	118.49 (14)	C19—C37—C33	122.60 (13)
C20—C19—C37	123.44 (13)	O2—C38—C25	119.00 (15)
C24—C19—C37	118.02 (14)	O2—C38—C31	120.72 (14)
C19—C20—C21	120.14 (16)	C25—C38—C31	120.29 (13)
C19—C20—H25	119.2 (9)	O3—C39—H5	111.3 (11)
C21—C20—H25	120.6 (10)	O3—C39—H7	109.6 (12)
C22—C21—C20	120.66 (18)	H5—C39—H7	105.2 (17)
C22—C21—H26	118.4 (11)	O3—C39—H6	104.2 (11)
C20—C21—H26	120.9 (11)	H5—C39—H6	111.6 (16)
C21—C22—C23	119.75 (17)	H7—C39—H6	114.9 (16)
C21—C22—H27	120.2 (10)	O4—C40—H17	106.7 (13)
C23—C22—H27	120.0 (10)	O4—C40—H18	113.2 (12)
C24—C23—C22	119.78 (18)	H17—C40—H18	114.8 (17)
C24—C23—H28	118.6 (11)	O4—C40—H19	113.2 (11)
C22—C23—H28	121.6 (11)	H17—C40—H19	107.3 (16)
C23—C24—C19	121.16 (17)	H18—C40—H19	101.7 (17)
C23—C24—H29	124.4 (9)	C34—O1—H12	113.3 (15)
C19—C24—H29	114.4 (9)	C6—O3—C39	118.31 (14)
C26—C25—C30	118.87 (18)	C16—O4—C40	117.48 (14)
C26—C25—C38	123.92 (16)
C6—C1—C2—C3	−0.5 (2)	C36—C31—C32—C33	−55.37 (16)
C1—C2—C3—C4	−0.4 (2)	C13—C32—C33—C37	−56.13 (16)
C1—C2—C3—C36	177.65 (14)	C31—C32—C33—C37	173.79 (12)
C2—C3—C4—C5	0.7 (2)	C13—C32—C33—C34	−176.92 (12)
C36—C3—C4—C5	−177.40 (14)	C31—C32—C33—C34	53.00 (16)
C3—C4—C5—C6	−0.2 (2)	C12—C7—C34—O1	17.2 (2)
C2—C1—C6—O3	−179.76 (13)	C8—C7—C34—O1	−165.65 (14)
C2—C1—C6—C5	1.1 (2)	C12—C7—C34—C35	133.59 (18)
C4—C5—C6—O3	180.00 (13)	C8—C7—C34—C35	−49.23 (19)
C4—C5—C6—C1	−0.7 (2)	C12—C7—C34—C33	−104.94 (18)
C12—C7—C8—C9	0.0 (3)	C8—C7—C34—C33	72.24 (17)
C34—C7—C8—C9	−177.35 (16)	C37—C33—C34—O1	−56.99 (15)
C7—C8—C9—C10	1.4 (3)	C32—C33—C34—O1	64.77 (15)
C8—C9—C10—C11	−1.2 (4)	C37—C33—C34—C7	64.31 (15)
C9—C10—C11—C12	−0.2 (5)	C32—C33—C34—C7	−173.93 (12)
C8—C7—C12—C11	−1.4 (3)	C37—C33—C34—C35	−173.43 (12)
C34—C7—C12—C11	175.9 (2)	C32—C33—C34—C35	−51.67 (16)
C10—C11—C12—C7	1.6 (4)	O1—C34—C35—C36	−64.42 (16)
C18—C13—C14—C15	−2.4 (2)	C7—C34—C35—C36	176.34 (13)
C32—C13—C14—C15	175.87 (13)	C33—C34—C35—C36	55.71 (17)
C13—C14—C15—C16	0.0 (2)	C2—C3—C36—C35	38.4 (2)
C14—C15—C16—C17	2.2 (2)	C4—C3—C36—C35	−143.62 (15)
C14—C15—C16—O4	−179.26 (12)	C2—C3—C36—C31	−88.77 (17)
C15—C16—C17—C18	−1.9 (2)	C4—C3—C36—C31	89.21 (17)
O4—C16—C17—C18	179.66 (14)	C34—C35—C36—C3	171.93 (12)
C14—C13—C18—C17	2.7 (2)	C34—C35—C36—C31	−60.12 (17)
C32—C13—C18—C17	−175.53 (14)	C38—C31—C36—C3	60.64 (15)
C16—C17—C18—C13	−0.6 (2)	C32—C31—C36—C3	−172.32 (12)
C24—C19—C20—C21	0.0 (2)	C38—C31—C36—C35	−68.72 (15)
C37—C19—C20—C21	−177.33 (14)	C32—C31—C36—C35	58.32 (16)
C19—C20—C21—C22	−1.4 (3)	C20—C19—C37—O5	162.66 (15)
C20—C21—C22—C23	1.4 (3)	C24—C19—C37—O5	−14.7 (2)
C21—C22—C23—C24	0.0 (3)	C20—C19—C37—C33	−19.9 (2)
C22—C23—C24—C19	−1.4 (3)	C24—C19—C37—C33	162.76 (13)
C20—C19—C24—C23	1.4 (2)	C32—C33—C37—O5	−53.93 (17)
C37—C19—C24—C23	178.85 (15)	C34—C33—C37—O5	69.07 (16)
C30—C25—C26—C27	−1.7 (3)	C32—C33—C37—C19	128.60 (13)
C38—C25—C26—C27	−179.99 (16)	C34—C33—C37—C19	−108.39 (14)
C25—C26—C27—C28	2.1 (3)	C26—C25—C38—O2	−164.01 (14)
C26—C27—C28—C29	−0.2 (5)	C30—C25—C38—O2	17.6 (2)
C27—C28—C29—C30	−2.1 (5)	C26—C25—C38—C31	16.2 (2)
C26—C25—C30—C29	−0.6 (4)	C30—C25—C38—C31	−162.13 (17)
C38—C25—C30—C29	177.8 (2)	C32—C31—C38—O2	−51.77 (17)
C28—C29—C30—C25	2.5 (5)	C36—C31—C38—O2	72.04 (16)
C18—C13—C32—C33	−63.79 (19)	C32—C31—C38—C25	128.00 (13)
C14—C13—C32—C33	118.03 (14)	C36—C31—C38—C25	−108.18 (14)
C18—C13—C32—C31	66.05 (18)	C1—C6—O3—C39	0.8 (2)
C14—C13—C32—C31	−112.13 (15)	C5—C6—O3—C39	−179.96 (16)
C38—C31—C32—C13	−60.92 (16)	C17—C16—O4—C40	−21.6 (2)
C36—C31—C32—C13	174.44 (12)	C15—C16—O4—C40	159.95 (17)
C38—C31—C32—C33	69.27 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H12···O5	0.84 (2)	2.07 (2)	2.7591 (16)	139 (2)
O1—H12···O5^i	0.84 (2)	2.33 (2)	2.9880 (17)	134.8 (19)

Symmetry code: (i) −x, −y, −z.