Agatholic acid

In agatholic acid, C₂₀H₃₂O₃, the two mol­ecules in the asymmetric unit have essentially the same conformation. The mol­ecules are linked by O—H...O hydrogen bonds between the carboxyl and alcohol groups.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.051
• wR factor = 0.126
• Data-to-parameter ratio = 6.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



THETM_01  Alert A The value of sine(theta_max)/wavelength is less than 0.550
          Calculated sin(theta_max)/wavelength =    0.5389

Author response: The diffraction of the crystal is very weak. Data were initially collected to 55\% 2\T, however significant diffraction was only observed to 45\% and the higher angle data was discarded.

 Alert Level C:



REFNR_01  Alert C Ratio of reflections to parameters is < 8 for a
          non-centrosymmetric structure, where ZMAX < 18
          sine(theta)/lambda                0.5389
          Proportion of unique data used    1.0000
          Ratio reflections to parameters   6.1575

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.114

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           22.52
         From the CIF: _reflns_number_total               2580
         Count of symmetry unique reflns         2581
         Completeness (_total/calc)             99.96%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          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.


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

Computing details

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

(I)

Crystal data

C20H32O3	F(000) = 704
Mr = 320.46	Dx = 1.118 Mg m^−3
Monoclinic, P21	Melting point: 457 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 7.7955 (14) Å	Cell parameters from 2540 reflections
b = 23.362 (4) Å	θ = 2.6–22.5°
c = 10.6973 (19) Å	µ = 0.07 mm^−1
β = 102.297 (3)°	T = 170 K
V = 1903.4 (6) Å^3	Plate, white
Z = 4	0.5 × 0.4 × 0.2 mm

Data collection

Bruker SMART CCD diffractometer	1596 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.114
Graphite monochromator	θmax = 22.5°, θmin = 1.7°
φ and ω scans	h = −8→8
15289 measured reflections	k = −25→25
2580 independent reflections	l = −11→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0582P)^2] where P = (Fo^2 + 2Fc^2)/3
2580 reflections	(Δ/σ)max = 0.002
419 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.21 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
O1	0.8190 (6)	0.46434 (18)	0.7794 (5)	0.0457 (13)
H1	0.9179	0.4544	0.7676	0.055*
O1A	1.9039 (6)	−0.01527 (18)	0.9524 (5)	0.0466 (13)
H1A	2.0064	−0.0266	0.9533	0.056*
C1A	1.4799 (8)	0.1313 (3)	0.7735 (7)	0.0389 (18)
H11A	1.4122	0.1569	0.8188	0.047*
H12A	1.4182	0.1300	0.6825	0.047*
C1	0.4313 (9)	0.6301 (3)	0.7329 (7)	0.048 (2)
H11	0.3667	0.6456	0.7956	0.058*
H12	0.3722	0.6440	0.6472	0.058*
O2	0.2725 (7)	0.8886 (2)	1.0716 (5)	0.0591 (15)
H32	0.2394	0.9166	1.1096	0.071*
O2A	1.2691 (8)	0.4113 (3)	0.9391 (5)	0.0749 (18)
H32A	1.2120	0.4388	0.9604	0.090*
C2	0.4199 (9)	0.5646 (3)	0.7342 (8)	0.051 (2)
H9	0.4661	0.5505	0.8222	0.061*
H10	0.2953	0.5528	0.7086	0.061*
C2A	1.4801 (9)	0.0711 (3)	0.8300 (7)	0.048 (2)
H9A	1.5292	0.0727	0.9232	0.058*
H10A	1.3579	0.0569	0.8169	0.058*
O3A	1.1411 (7)	0.4412 (2)	0.7440 (5)	0.0646 (16)
O3	0.2128 (7)	0.9484 (2)	0.9067 (5)	0.0623 (16)
C3A	1.5875 (9)	0.0298 (3)	0.7685 (7)	0.046 (2)
H7A	1.5288	0.0245	0.6776	0.056*
H8A	1.5899	−0.0079	0.8113	0.056*
C3	0.5224 (9)	0.5378 (3)	0.6448 (7)	0.054 (2)
H7	0.4672	0.5485	0.5559	0.064*
H8	0.5156	0.4956	0.6516	0.064*
C4A	1.7768 (9)	0.0495 (3)	0.7752 (7)	0.0377 (18)
C4	0.7164 (9)	0.5557 (3)	0.6722 (6)	0.0417 (19)
C5A	1.7754 (8)	0.1124 (3)	0.7261 (6)	0.0332 (17)
H16A	1.7153	0.1096	0.6339	0.040*
C5	0.7296 (8)	0.6219 (3)	0.6800 (6)	0.0364 (18)
H16	0.6759	0.6348	0.5911	0.044*
C6	0.9177 (9)	0.6440 (3)	0.7022 (7)	0.050 (2)
H17	0.9821	0.6235	0.6455	0.060*
H18	0.9782	0.6368	0.7919	0.060*
C6A	1.9571 (8)	0.1357 (3)	0.7217 (7)	0.0433 (19)
H17A	2.0227	0.1067	0.6831	0.052*
H18A	2.0233	0.1433	0.8099	0.052*
C7A	1.9415 (9)	0.1908 (3)	0.6434 (8)	0.053 (2)
H19A	2.0598	0.2074	0.6489	0.063*
H20A	1.8912	0.1820	0.5524	0.063*
C7	0.9176 (10)	0.7091 (3)	0.6741 (9)	0.062 (2)
H19	1.0393	0.7238	0.6975	0.074*
H20	0.8737	0.7156	0.5813	0.074*
C8	0.8038 (10)	0.7417 (3)	0.7480 (8)	0.052 (2)
C8A	1.8267 (9)	0.2339 (3)	0.6908 (7)	0.0424 (19)
C9A	1.6482 (8)	0.2120 (3)	0.6970 (7)	0.0355 (18)
H23A	1.5921	0.1996	0.6082	0.043*
C9	0.6166 (9)	0.7181 (3)	0.7271 (7)	0.0389 (18)
H23	0.5675	0.7199	0.6329	0.047*
C10A	1.6631 (8)	0.1572 (3)	0.7817 (6)	0.0333 (17)
C10	0.6199 (9)	0.6534 (3)	0.7645 (6)	0.0375 (18)
C11A	1.5287 (9)	0.2591 (3)	0.7332 (7)	0.0404 (18)
H24A	1.4307	0.2409	0.7639	0.049*
H25A	1.5971	0.2821	0.8044	0.049*
C11	0.4981 (10)	0.7556 (3)	0.7896 (7)	0.0445 (19)
H24	0.5635	0.7685	0.8746	0.053*
H25	0.3955	0.7331	0.8020	0.053*
C12	0.4357 (10)	0.8076 (3)	0.7056 (7)	0.049 (2)
H26	0.5389	0.8241	0.6785	0.058*
H27	0.3543	0.7938	0.6275	0.058*
C12A	1.4541 (9)	0.2985 (3)	0.6226 (7)	0.046 (2)
H26A	1.5531	0.3136	0.5879	0.056*
H27A	1.3802	0.2753	0.5543	0.056*
C13	0.3446 (9)	0.8557 (3)	0.7616 (7)	0.0413 (19)
C13A	1.3458 (9)	0.3488 (3)	0.6504 (7)	0.0386 (18)
C14A	1.3361 (9)	0.3610 (3)	0.7682 (8)	0.046 (2)
H31A	1.3990	0.3364	0.8327	0.055*
C14	0.3405 (9)	0.8570 (3)	0.8837 (8)	0.047 (2)
H31	0.3892	0.8249	0.9332	0.057*
C15A	1.2395 (10)	0.4081 (3)	0.8123 (9)	0.050 (2)
C15	0.2692 (10)	0.9025 (4)	0.9521 (8)	0.051 (2)
C16	0.2723 (10)	0.9011 (3)	0.6662 (7)	0.062 (2)
H28	0.2137	0.9305	0.7074	0.093*
H29	0.1876	0.8839	0.5951	0.093*
H30	0.3683	0.9186	0.6335	0.093*
C16A	1.2576 (12)	0.3811 (4)	0.5339 (8)	0.083 (3)
H28A	1.1929	0.4136	0.5591	0.125*
H29A	1.1758	0.3557	0.4773	0.125*
H30A	1.3462	0.3952	0.4888	0.125*
C17A	1.8897 (10)	0.2856 (4)	0.7256 (9)	0.079 (3)
H21A	1.8192	0.3126	0.7580	0.095*
H22A	2.0052	0.2955	0.7180	0.095*
C17	0.8671 (10)	0.7847 (4)	0.8199 (9)	0.076 (3)
H21	0.9858	0.7960	0.8264	0.091*
H22	0.7948	0.8050	0.8659	0.091*
C18A	1.8582 (10)	0.0103 (3)	0.6873 (7)	0.050 (2)
H4A	1.8621	−0.0291	0.7190	0.076*
H5A	1.9775	0.0233	0.6868	0.076*
H6A	1.7865	0.0118	0.6001	0.076*
C18	0.7979 (10)	0.5338 (3)	0.5607 (7)	0.056 (2)
H4	0.7372	0.5516	0.4804	0.083*
H5	0.7852	0.4921	0.5538	0.083*
H6	0.9227	0.5439	0.5774	0.083*
C19	0.8147 (9)	0.5259 (3)	0.7939 (7)	0.0410 (19)
H2	0.9365	0.5406	0.8161	0.049*
H3	0.7571	0.5354	0.8653	0.049*
C19A	1.8866 (9)	0.0436 (3)	0.9130 (7)	0.0420 (19)
H2A	2.0047	0.0601	0.9175	0.050*
H3A	1.8295	0.0654	0.9723	0.050*
C20	0.6953 (9)	0.6469 (3)	0.9093 (6)	0.0432 (19)
H13	0.6977	0.6063	0.9326	0.065*
H14	0.6212	0.6679	0.9571	0.065*
H15	0.8148	0.6624	0.9303	0.065*
C20A	1.7399 (9)	0.1748 (3)	0.9231 (6)	0.047 (2)
H13A	1.7515	0.1408	0.9778	0.070*
H14A	1.6610	0.2023	0.9512	0.070*
H15A	1.8556	0.1924	0.9293	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.042 (3)	0.037 (3)	0.060 (4)	0.007 (2)	0.016 (3)	0.002 (2)
O1A	0.043 (3)	0.039 (3)	0.060 (4)	0.007 (2)	0.017 (3)	0.013 (3)
C1A	0.028 (4)	0.035 (4)	0.058 (5)	0.002 (3)	0.018 (4)	0.006 (4)
C1	0.040 (5)	0.052 (5)	0.053 (5)	−0.001 (4)	0.012 (4)	0.004 (4)
O2	0.079 (4)	0.051 (4)	0.054 (4)	0.023 (3)	0.029 (3)	0.003 (3)
O2A	0.088 (5)	0.080 (5)	0.054 (4)	0.040 (3)	0.008 (3)	−0.018 (3)
C2	0.035 (4)	0.040 (5)	0.078 (6)	−0.004 (4)	0.013 (4)	0.002 (4)
C2A	0.038 (5)	0.042 (5)	0.067 (6)	0.005 (4)	0.019 (4)	0.010 (4)
O3A	0.069 (4)	0.059 (4)	0.073 (4)	0.022 (3)	0.032 (3)	0.005 (3)
O3	0.076 (4)	0.045 (4)	0.071 (4)	0.028 (3)	0.025 (3)	0.012 (3)
C3A	0.056 (5)	0.029 (4)	0.049 (5)	−0.004 (4)	0.001 (4)	−0.002 (4)
C3	0.036 (5)	0.057 (5)	0.063 (6)	0.010 (4)	−0.001 (4)	−0.007 (4)
C4A	0.040 (5)	0.034 (4)	0.041 (5)	0.005 (3)	0.013 (4)	−0.003 (3)
C4	0.049 (5)	0.046 (5)	0.030 (4)	0.004 (4)	0.005 (4)	−0.003 (4)
C5A	0.035 (4)	0.031 (4)	0.036 (4)	0.006 (3)	0.015 (3)	−0.003 (3)
C5	0.043 (4)	0.035 (4)	0.035 (4)	0.017 (3)	0.017 (3)	0.003 (3)
C6	0.041 (5)	0.051 (5)	0.064 (6)	0.009 (4)	0.028 (4)	0.006 (4)
C6A	0.037 (5)	0.044 (5)	0.054 (5)	0.009 (4)	0.022 (4)	0.007 (4)
C7A	0.040 (4)	0.052 (5)	0.072 (6)	0.000 (4)	0.026 (4)	0.010 (4)
C7	0.058 (5)	0.041 (5)	0.101 (7)	0.004 (4)	0.047 (5)	0.002 (5)
C8	0.048 (5)	0.036 (5)	0.076 (6)	0.001 (4)	0.025 (5)	0.010 (4)
C8A	0.037 (4)	0.038 (5)	0.055 (5)	0.004 (4)	0.014 (4)	0.005 (4)
C9A	0.037 (4)	0.022 (4)	0.051 (5)	0.009 (3)	0.017 (4)	−0.001 (3)
C9	0.041 (4)	0.032 (4)	0.047 (5)	0.005 (3)	0.016 (4)	0.001 (4)
C10A	0.032 (4)	0.037 (4)	0.033 (4)	0.000 (3)	0.011 (3)	−0.007 (3)
C10	0.036 (4)	0.036 (4)	0.042 (5)	0.003 (3)	0.010 (4)	−0.001 (3)
C11A	0.043 (4)	0.033 (4)	0.048 (5)	0.006 (3)	0.016 (4)	0.001 (4)
C11	0.052 (5)	0.038 (4)	0.049 (5)	0.006 (4)	0.023 (4)	0.005 (4)
C12	0.061 (5)	0.041 (5)	0.046 (5)	0.018 (4)	0.017 (4)	0.010 (4)
C12A	0.055 (5)	0.042 (5)	0.044 (5)	0.018 (4)	0.014 (4)	−0.001 (4)
C13	0.039 (4)	0.040 (5)	0.047 (5)	0.007 (4)	0.014 (4)	0.009 (4)
C13A	0.040 (4)	0.037 (4)	0.038 (5)	0.008 (4)	0.007 (4)	0.002 (4)
C14A	0.039 (4)	0.034 (5)	0.064 (6)	0.009 (4)	0.008 (4)	0.001 (4)
C14	0.046 (5)	0.036 (5)	0.063 (6)	0.011 (4)	0.020 (4)	0.003 (4)
C15A	0.045 (5)	0.040 (5)	0.067 (6)	0.011 (4)	0.017 (5)	0.002 (5)
C15	0.052 (5)	0.049 (6)	0.057 (6)	0.004 (4)	0.022 (5)	−0.003 (5)
C16	0.068 (6)	0.054 (6)	0.066 (6)	0.020 (5)	0.017 (5)	0.013 (5)
C16A	0.106 (7)	0.081 (7)	0.061 (6)	0.054 (6)	0.014 (6)	0.010 (5)
C17A	0.067 (6)	0.046 (6)	0.137 (9)	−0.008 (5)	0.046 (6)	−0.021 (6)
C17	0.054 (5)	0.057 (6)	0.124 (9)	−0.013 (5)	0.031 (6)	−0.027 (6)
C18A	0.052 (5)	0.049 (5)	0.049 (5)	0.011 (4)	0.009 (4)	−0.005 (4)
C18	0.066 (5)	0.057 (5)	0.047 (5)	0.017 (4)	0.018 (4)	−0.008 (4)
C19	0.048 (5)	0.024 (4)	0.049 (5)	0.006 (3)	0.005 (4)	−0.001 (4)
C19A	0.049 (5)	0.025 (4)	0.051 (5)	0.003 (3)	0.009 (4)	0.004 (3)
C20	0.053 (5)	0.045 (5)	0.034 (5)	0.006 (4)	0.015 (4)	−0.001 (4)
C20A	0.042 (5)	0.052 (5)	0.046 (5)	0.003 (4)	0.009 (4)	−0.007 (4)

Geometric parameters (Å, º)

O1—C19	1.448 (7)	C8A—C17A	1.326 (9)
O1—H1	0.8400	C8A—C9A	1.497 (9)
O1A—C19A	1.435 (7)	C9A—C11A	1.544 (8)
O1A—H1A	0.8400	C9A—C10A	1.557 (9)
C1A—C2A	1.531 (8)	C9A—H23A	1.0000
C1A—C10A	1.537 (8)	C9—C11	1.526 (9)
C1A—H11A	0.9900	C9—C10	1.562 (9)
C1A—H12A	0.9900	C9—H23	1.0000
C1—C2	1.533 (9)	C10A—C20A	1.559 (9)
C1—C10	1.537 (9)	C10—C20	1.543 (9)
C1—H11	0.9900	C11A—C12A	1.514 (9)
C1—H12	0.9900	C11A—H24A	0.9900
O2—C15	1.314 (9)	C11A—H25A	0.9900
O2—H32	0.8400	C11—C12	1.526 (9)
O2A—C15A	1.329 (9)	C11—H24	0.9900
O2A—H32A	0.8400	C11—H25	0.9900
C2—C3	1.507 (10)	C12—C13	1.520 (9)
C2—H9	0.9900	C12—H26	0.9900
C2—H10	0.9900	C12—H27	0.9900
C2A—C3A	1.516 (9)	C12A—C13A	1.513 (9)
C2A—H9A	0.9900	C12A—H26A	0.9900
C2A—H10A	0.9900	C12A—H27A	0.9900
O3A—C15A	1.219 (8)	C13—C14	1.314 (9)
O3—C15	1.220 (8)	C13—C16	1.496 (9)
C3A—C4A	1.532 (9)	C13A—C14A	1.310 (9)
C3A—H7A	0.9900	C13A—C16A	1.493 (9)
C3A—H8A	0.9900	C14A—C15A	1.466 (10)
C3—C4	1.536 (9)	C14A—H31A	0.9500
C3—H7	0.9900	C14—C15	1.464 (10)
C3—H8	0.9900	C14—H31	0.9500
C4A—C18A	1.542 (9)	C16—H28	0.9800
C4A—C19A	1.546 (9)	C16—H29	0.9800
C4A—C5A	1.561 (9)	C16—H30	0.9800
C4—C19	1.529 (9)	C16A—H28A	0.9800
C4—C5	1.552 (9)	C16A—H29A	0.9800
C4—C18	1.553 (9)	C16A—H30A	0.9800
C5A—C6A	1.526 (9)	C17A—H21A	0.9500
C5A—C10A	1.562 (8)	C17A—H22A	0.9500
C5A—H16A	1.0000	C17—H21	0.9500
C5—C6	1.525 (9)	C17—H22	0.9500
C5—C10	1.556 (8)	C18A—H4A	0.9800
C5—H16	1.0000	C18A—H5A	0.9800
C6—C7	1.550 (10)	C18A—H6A	0.9800
C6—H17	0.9900	C18—H4	0.9800
C6—H18	0.9900	C18—H5	0.9800
C6A—C7A	1.528 (9)	C18—H6	0.9800
C6A—H17A	0.9900	C19—H2	0.9900
C6A—H18A	0.9900	C19—H3	0.9900
C7A—C8A	1.504 (9)	C19A—H2A	0.9900
C7A—H19A	0.9900	C19A—H3A	0.9900
C7A—H20A	0.9900	C20—H13	0.9800
C7—C8	1.512 (10)	C20—H14	0.9800
C7—H19	0.9900	C20—H15	0.9800
C7—H20	0.9900	C20A—H13A	0.9800
C8—C17	1.299 (10)	C20A—H14A	0.9800
C8—C9	1.531 (10)	C20A—H15A	0.9800
C19—O1—H1	109.5	C1A—C10A—C20A	108.6 (5)
C19A—O1A—H1A	109.5	C9A—C10A—C20A	108.3 (5)
C2A—C1A—C10A	114.7 (6)	C1A—C10A—C5A	107.7 (5)
C2A—C1A—H11A	108.6	C9A—C10A—C5A	107.9 (5)
C10A—C1A—H11A	108.6	C20A—C10A—C5A	114.5 (5)
C2A—C1A—H12A	108.6	C1—C10—C20	109.1 (6)
C10A—C1A—H12A	108.6	C1—C10—C5	108.8 (5)
H11A—C1A—H12A	107.6	C20—C10—C5	113.4 (5)
C2—C1—C10	114.0 (6)	C1—C10—C9	108.9 (5)
C2—C1—H11	108.7	C20—C10—C9	109.6 (5)
C10—C1—H11	108.7	C5—C10—C9	106.8 (5)
C2—C1—H12	108.7	C12A—C11A—C9A	112.9 (6)
C10—C1—H12	108.7	C12A—C11A—H24A	109.0
H11—C1—H12	107.6	C9A—C11A—H24A	109.0
C15—O2—H32	109.5	C12A—C11A—H25A	109.0
C15A—O2A—H32A	109.5	C9A—C11A—H25A	109.0
C3—C2—C1	111.7 (6)	H24A—C11A—H25A	107.8
C3—C2—H9	109.3	C9—C11—C12	110.2 (6)
C1—C2—H9	109.3	C9—C11—H24	109.6
C3—C2—H10	109.3	C12—C11—H24	109.6
C1—C2—H10	109.3	C9—C11—H25	109.6
H9—C2—H10	107.9	C12—C11—H25	109.6
C3A—C2A—C1A	111.6 (6)	H24—C11—H25	108.1
C3A—C2A—H9A	109.3	C13—C12—C11	118.3 (6)
C1A—C2A—H9A	109.3	C13—C12—H26	107.7
C3A—C2A—H10A	109.3	C11—C12—H26	107.7
C1A—C2A—H10A	109.3	C13—C12—H27	107.7
H9A—C2A—H10A	108.0	C11—C12—H27	107.7
C2A—C3A—C4A	113.8 (6)	H26—C12—H27	107.1
C2A—C3A—H7A	108.8	C13A—C12A—C11A	117.1 (6)
C4A—C3A—H7A	108.8	C13A—C12A—H26A	108.0
C2A—C3A—H8A	108.8	C11A—C12A—H26A	108.0
C4A—C3A—H8A	108.8	C13A—C12A—H27A	108.0
H7A—C3A—H8A	107.7	C11A—C12A—H27A	108.0
C2—C3—C4	113.5 (6)	H26A—C12A—H27A	107.3
C2—C3—H7	108.9	C14—C13—C16	125.2 (7)
C4—C3—H7	108.9	C14—C13—C12	121.5 (6)
C2—C3—H8	108.9	C16—C13—C12	113.3 (6)
C4—C3—H8	108.9	C14A—C13A—C16A	125.7 (7)
H7—C3—H8	107.7	C14A—C13A—C12A	120.4 (6)
C3A—C4A—C18A	108.1 (6)	C16A—C13A—C12A	113.9 (6)
C3A—C4A—C19A	110.5 (6)	C13A—C14A—C15A	127.7 (7)
C18A—C4A—C19A	108.2 (5)	C13A—C14A—H31A	116.2
C3A—C4A—C5A	109.3 (5)	C15A—C14A—H31A	116.2
C18A—C4A—C5A	109.2 (5)	C13—C14—C15	127.3 (7)
C19A—C4A—C5A	111.6 (5)	C13—C14—H31	116.3
C19—C4—C3	109.5 (6)	C15—C14—H31	116.3
C19—C4—C5	113.1 (5)	O3A—C15A—O2A	121.8 (7)
C3—C4—C5	109.5 (6)	O3A—C15A—C14A	125.8 (8)
C19—C4—C18	106.9 (6)	O2A—C15A—C14A	112.4 (7)
C3—C4—C18	108.1 (6)	O3—C15—O2	122.3 (7)
C5—C4—C18	109.6 (6)	O3—C15—C14	125.6 (8)
C6A—C5A—C4A	113.9 (5)	O2—C15—C14	112.1 (7)
C6A—C5A—C10A	111.9 (5)	C13—C16—H28	109.5
C4A—C5A—C10A	117.9 (5)	C13—C16—H29	109.5
C6A—C5A—H16A	103.7	H28—C16—H29	109.5
C4A—C5A—H16A	103.7	C13—C16—H30	109.5
C10A—C5A—H16A	103.7	H28—C16—H30	109.5
C6—C5—C4	113.4 (5)	H29—C16—H30	109.5
C6—C5—C10	112.3 (6)	C13A—C16A—H28A	109.5
C4—C5—C10	117.7 (6)	C13A—C16A—H29A	109.5
C6—C5—H16	103.9	H28A—C16A—H29A	109.5
C4—C5—H16	103.9	C13A—C16A—H30A	109.5
C10—C5—H16	103.9	H28A—C16A—H30A	109.5
C5—C6—C7	109.9 (6)	H29A—C16A—H30A	109.5
C5—C6—H17	109.7	C8A—C17A—H21A	120.0
C7—C6—H17	109.7	C8A—C17A—H22A	120.0
C5—C6—H18	109.7	H21A—C17A—H22A	120.0
C7—C6—H18	109.7	C8—C17—H21	120.0
H17—C6—H18	108.2	C8—C17—H22	120.0
C5A—C6A—C7A	110.5 (5)	H21—C17—H22	120.0
C5A—C6A—H17A	109.5	C4A—C18A—H4A	109.5
C7A—C6A—H17A	109.5	C4A—C18A—H5A	109.5
C5A—C6A—H18A	109.5	H4A—C18A—H5A	109.5
C7A—C6A—H18A	109.5	C4A—C18A—H6A	109.5
H17A—C6A—H18A	108.1	H4A—C18A—H6A	109.5
C8A—C7A—C6A	111.2 (6)	H5A—C18A—H6A	109.5
C8A—C7A—H19A	109.4	C4—C18—H4	109.5
C6A—C7A—H19A	109.4	C4—C18—H5	109.5
C8A—C7A—H20A	109.4	H4—C18—H5	109.5
C6A—C7A—H20A	109.4	C4—C18—H6	109.5
H19A—C7A—H20A	108.0	H4—C18—H6	109.5
C8—C7—C6	111.6 (6)	H5—C18—H6	109.5
C8—C7—H19	109.3	O1—C19—C4	112.3 (5)
C6—C7—H19	109.3	O1—C19—H2	109.1
C8—C7—H20	109.3	C4—C19—H2	109.1
C6—C7—H20	109.3	O1—C19—H3	109.1
H19—C7—H20	108.0	C4—C19—H3	109.1
C17—C8—C7	120.5 (7)	H2—C19—H3	107.9
C17—C8—C9	126.5 (7)	O1A—C19A—C4A	111.3 (5)
C7—C8—C9	113.0 (7)	O1A—C19A—H2A	109.4
C17A—C8A—C9A	126.2 (7)	C4A—C19A—H2A	109.4
C17A—C8A—C7A	119.5 (7)	O1A—C19A—H3A	109.4
C9A—C8A—C7A	114.3 (6)	C4A—C19A—H3A	109.4
C8A—C9A—C11A	112.6 (5)	H2A—C19A—H3A	108.0
C8A—C9A—C10A	110.6 (5)	C10—C20—H13	109.5
C11A—C9A—C10A	114.5 (5)	C10—C20—H14	109.5
C8A—C9A—H23A	106.2	H13—C20—H14	109.5
C11A—C9A—H23A	106.2	C10—C20—H15	109.5
C10A—C9A—H23A	106.2	H13—C20—H15	109.5
C11—C9—C8	112.2 (6)	H14—C20—H15	109.5
C11—C9—C10	114.9 (6)	C10A—C20A—H13A	109.5
C8—C9—C10	110.3 (6)	C10A—C20A—H14A	109.5
C11—C9—H23	106.3	H13A—C20A—H14A	109.5
C8—C9—H23	106.3	C10A—C20A—H15A	109.5
C10—C9—H23	106.3	H13A—C20A—H15A	109.5
C1A—C10A—C9A	109.7 (5)	H14A—C20A—H15A	109.5
C10—C1—C2—C3	−56.0 (9)	C8A—C9A—C10A—C5A	−56.0 (7)
C10A—C1A—C2A—C3A	−56.2 (8)	C11A—C9A—C10A—C5A	175.6 (5)
C1A—C2A—C3A—C4A	55.2 (8)	C6A—C5A—C10A—C1A	176.3 (6)
C1—C2—C3—C4	56.1 (9)	C4A—C5A—C10A—C1A	−48.8 (7)
C2A—C3A—C4A—C18A	−169.0 (6)	C6A—C5A—C10A—C9A	57.9 (7)
C2A—C3A—C4A—C19A	72.8 (7)	C4A—C5A—C10A—C9A	−167.2 (5)
C2A—C3A—C4A—C5A	−50.3 (8)	C6A—C5A—C10A—C20A	−62.8 (7)
C2—C3—C4—C19	73.4 (8)	C4A—C5A—C10A—C20A	72.1 (7)
C2—C3—C4—C5	−51.0 (8)	C2—C1—C10—C20	−74.5 (8)
C2—C3—C4—C18	−170.4 (6)	C2—C1—C10—C5	49.8 (8)
C3A—C4A—C5A—C6A	−177.0 (6)	C2—C1—C10—C9	165.9 (6)
C18A—C4A—C5A—C6A	−59.0 (7)	C6—C5—C10—C1	178.1 (6)
C19A—C4A—C5A—C6A	60.6 (7)	C4—C5—C10—C1	−47.6 (8)
C3A—C4A—C5A—C10A	49.0 (8)	C6—C5—C10—C20	−60.2 (7)
C18A—C4A—C5A—C10A	167.0 (6)	C4—C5—C10—C20	74.1 (8)
C19A—C4A—C5A—C10A	−73.5 (7)	C6—C5—C10—C9	60.6 (7)
C19—C4—C5—C6	59.8 (8)	C4—C5—C10—C9	−165.1 (6)
C3—C4—C5—C6	−177.9 (6)	C11—C9—C10—C1	56.3 (8)
C18—C4—C5—C6	−59.5 (8)	C8—C9—C10—C1	−175.7 (6)
C19—C4—C5—C10	−74.1 (8)	C11—C9—C10—C20	−63.0 (8)
C3—C4—C5—C10	48.3 (8)	C8—C9—C10—C20	64.9 (7)
C18—C4—C5—C10	166.7 (6)	C11—C9—C10—C5	173.7 (6)
C4—C5—C6—C7	165.5 (6)	C8—C9—C10—C5	−58.3 (7)
C10—C5—C6—C7	−58.2 (8)	C8A—C9A—C11A—C12A	77.4 (8)
C4A—C5A—C6A—C7A	166.1 (6)	C10A—C9A—C11A—C12A	−155.2 (6)
C10A—C5A—C6A—C7A	−57.1 (8)	C8—C9—C11—C12	79.7 (8)
C5A—C6A—C7A—C8A	53.3 (8)	C10—C9—C11—C12	−153.3 (6)
C5—C6—C7—C8	53.0 (9)	C9—C11—C12—C13	−168.8 (6)
C6—C7—C8—C17	126.3 (9)	C9A—C11A—C12A—C13A	−175.7 (6)
C6—C7—C8—C9	−53.7 (9)	C11—C12—C13—C14	9.4 (11)
C6A—C7A—C8A—C17A	124.0 (8)	C11—C12—C13—C16	−173.7 (7)
C6A—C7A—C8A—C9A	−54.3 (8)	C11A—C12A—C13A—C14A	7.9 (10)
C17A—C8A—C9A—C11A	7.5 (11)	C11A—C12A—C13A—C16A	−172.4 (7)
C7A—C8A—C9A—C11A	−174.3 (6)	C16A—C13A—C14A—C15A	−0.3 (13)
C17A—C8A—C9A—C10A	−122.0 (8)	C12A—C13A—C14A—C15A	179.3 (7)
C7A—C8A—C9A—C10A	56.3 (8)	C16—C13—C14—C15	−1.3 (13)
C17—C8—C9—C11	6.7 (12)	C12—C13—C14—C15	175.3 (7)
C7—C8—C9—C11	−173.3 (6)	C13A—C14A—C15A—O3A	5.9 (13)
C17—C8—C9—C10	−122.8 (9)	C13A—C14A—C15A—O2A	−174.6 (7)
C7—C8—C9—C10	57.2 (8)	C13—C14—C15—O3	−5.4 (13)
C2A—C1A—C10A—C9A	168.1 (6)	C13—C14—C15—O2	174.9 (8)
C2A—C1A—C10A—C20A	−73.7 (7)	C3—C4—C19—O1	64.6 (7)
C2A—C1A—C10A—C5A	50.9 (7)	C5—C4—C19—O1	−173.0 (5)
C8A—C9A—C10A—C1A	−173.1 (6)	C18—C4—C19—O1	−52.3 (8)
C11A—C9A—C10A—C1A	58.5 (7)	C3A—C4A—C19A—O1A	64.8 (7)
C8A—C9A—C10A—C20A	68.5 (7)	C18A—C4A—C19A—O1A	−53.4 (7)
C11A—C9A—C10A—C20A	−59.9 (7)	C5A—C4A—C19A—O1A	−173.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O3^i	0.84	1.88	2.694 (7)	164
O2—H32···O1^ii	0.84	1.76	2.582 (7)	166
O2A—H32A···O1A^iii	0.84	1.79	2.603 (6)	163
O1—H1···O3A	0.84	1.84	2.673 (7)	174

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