Absolute configuration of 14β-hydroxy-3β-O-(L-theve­tosyl)-5β-card-20(22)-enolide chloro­form disolvate

The structure of 14β-hydroxy-3β-O-(L-theve­tosyl)-5β-card-20(22)-enolide, C₃₀H₄₆O₈, (I), has been reported previously [Chantrapromma et al. (2003). Acta Cryst. C59, o68–o70] in the assumed L form. In order to establish the absolute configur­ation of this important naturally occurring triterpenoidal glycoside, we have successfully incorporated chloro­form mol­ecules in the crystal structure by using chloro­form as a solvent during crystallization, viz. C₃₀H₄₆O₈·2CHCl₃, (I). The present X-ray study confirms that the previously assumed stereochemistry, viz. the L form, is correct. As previously reported, the steroid nucleus has a cis/trans/cis configuration. However, the present structure differs from that reported earlier in the orientations of the lactone ring and glycosidic linkages.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in solvent or counterion
• R factor = 0.077
• wR factor = 0.227
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X       H8O    ..  H31B     =       1.96 Ang.
PLAT415_ALERT_2_B Short Inter D-H..H-X       H8O    ..  H31A     =       1.91 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O6     -   H6O    ...          ?
PLAT420_ALERT_2_B D-H Without Acceptor       O8     -   H8O    ...          ?

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C6
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C16
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C21
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C20
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C23
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        C31
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        C32
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      11.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               6626
           Count of symmetry unique reflns         3881
           Completeness (_total/calc)            170.73%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2745
           Fraction of Friedel pairs measured     0.707
           Are heavy atom types Z>Si present          yes

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

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

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

14β-hydroxy-3β-o-(L-thevetosyl)-5β-card-20 (22)-enolide dichloroform solvate

Crystal data

C30H46O8·2CHCl3	F(000) = 1624
Mr = 773.40	Dx = 1.345 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6197 reflections
a = 7.6426 (4) Å	θ = 2.3–25.4°
b = 9.1932 (5) Å	µ = 0.50 mm^−1
c = 54.362 (3) Å	T = 293 K
V = 3819.5 (4) Å^3	Block, colourless
Z = 4	0.36 × 0.34 × 0.24 mm

Data collection

Siemens SMART CCD area-detector diffractometer	6626 independent reflections
Radiation source: fine-focus sealed tube	4427 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.3°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→8
Tmin = 0.798, Tmax = 0.891	l = −62→64
18659 measured reflections

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)] = 0.077	H-atom parameters constrained
wR(F^2) = 0.227	w = 1/[σ^2(Fo^2) + (0.1044P)^2 + 4.0909P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
6626 reflections	Δρmax = 0.33 e Å^−3
422 parameters	Δρmin = −0.40 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2780 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.14 (14)

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	Occ. (<1)
Cl1	0.6612 (8)	0.7344 (7)	0.40161 (10)	0.243 (2)
Cl2A	0.8353 (11)	0.5328 (6)	0.44180 (16)	0.146 (3)	0.491 (8)
Cl2B	0.7629 (11)	0.4902 (6)	0.42287 (16)	0.146 (3)	0.51
Cl3	1.0242 (5)	0.7019 (3)	0.40842 (5)	0.1322 (11)
Cl4	0.4633 (4)	0.4371 (5)	0.24380 (4)	0.1578 (14)
Cl5	0.3480 (4)	0.6578 (3)	0.20839 (6)	0.1309 (10)
Cl6	0.4847 (4)	0.3894 (3)	0.19260 (4)	0.1141 (8)
O1	0.0072 (7)	0.8137 (5)	0.25319 (7)	0.0802 (14)
O2	0.1924 (5)	0.0635 (4)	0.44115 (6)	0.0485 (9)
O3	0.3681 (5)	0.1501 (4)	0.47335 (6)	0.0541 (10)
O4	−0.1468 (6)	0.6705 (5)	0.22887 (6)	0.0670 (12)
O5	−0.0601 (5)	0.3446 (4)	0.30671 (6)	0.0501 (9)
H5O	0.0162	0.3247	0.2966	0.075*
O6	0.0470 (7)	−0.1399 (7)	0.47281 (10)	0.0920 (17)
H6O	0.0590	−0.1949	0.4611	0.138*
O7	0.3610 (8)	−0.2942 (5)	0.48356 (8)	0.0801 (15)
O8	0.6706 (7)	−0.1580 (7)	0.46756 (11)	0.0985 (18)
H8O	0.7243	−0.1107	0.4572	0.148*
C1	0.3856 (9)	0.2477 (7)	0.40354 (11)	0.0655 (18)
H1A	0.4677	0.3256	0.4001	0.079*
H1B	0.4519	0.1669	0.4102	0.079*
C2	0.2580 (10)	0.3000 (7)	0.42305 (11)	0.0687 (19)
H2A	0.3216	0.3227	0.4380	0.082*
H2B	0.2012	0.3883	0.4174	0.082*
C3	0.1202 (9)	0.1855 (6)	0.42854 (9)	0.0551 (15)
H3	0.0289	0.2290	0.4388	0.066*
C4	0.0373 (8)	0.1299 (6)	0.40498 (10)	0.0528 (14)
H4A	−0.0354	0.2063	0.3981	0.063*
H4B	−0.0384	0.0486	0.4090	0.063*
C5	0.1676 (8)	0.0812 (6)	0.38544 (8)	0.0520 (14)
H5	0.2319	−0.0015	0.3923	0.062*
C6	0.0755 (12)	0.0265 (7)	0.36254 (11)	0.082 (2)
H6A	−0.0111	−0.0455	0.3672	0.099*
H6B	0.1602	−0.0205	0.3519	0.099*
C7	−0.0145 (11)	0.1492 (7)	0.34837 (11)	0.078 (2)
H7A	−0.1115	0.1861	0.3580	0.094*
H7B	−0.0616	0.1108	0.3331	0.094*
C8	0.1110 (8)	0.2744 (6)	0.34251 (9)	0.0450 (13)
H8	0.1981	0.2348	0.3311	0.054*
C9	0.2140 (7)	0.3267 (6)	0.36535 (8)	0.0425 (12)
H9	0.1273	0.3680	0.3766	0.051*
C10	0.3037 (8)	0.1997 (6)	0.37951 (9)	0.0501 (13)
C11	0.3343 (8)	0.4502 (7)	0.35827 (11)	0.0612 (17)
H11A	0.4224	0.4144	0.3470	0.073*
H11B	0.3938	0.4856	0.3729	0.073*
C12	0.2360 (9)	0.5750 (7)	0.34632 (10)	0.0602 (16)
H12A	0.3185	0.6514	0.3422	0.072*
H12B	0.1532	0.6146	0.3581	0.072*
C13	0.1358 (8)	0.5295 (5)	0.32267 (8)	0.0426 (12)
C14	0.0194 (7)	0.3970 (5)	0.32881 (8)	0.0402 (12)
C15	−0.1343 (8)	0.4655 (8)	0.34289 (10)	0.0626 (17)
H15A	−0.2366	0.4033	0.3421	0.075*
H15B	−0.1036	0.4811	0.3600	0.075*
C16	−0.1691 (11)	0.6108 (8)	0.32992 (12)	0.083 (2)
H16A	−0.2627	0.6002	0.3180	0.099*
H16B	−0.2028	0.6844	0.3418	0.099*
C17	0.0012 (9)	0.6549 (6)	0.31698 (9)	0.0539 (15)
H17	0.0443	0.7438	0.3249	0.065*
C18	0.2672 (8)	0.4988 (7)	0.30198 (10)	0.0578 (15)
H18A	0.3439	0.4213	0.3069	0.087*
H18B	0.3346	0.5848	0.2988	0.087*
H18C	0.2052	0.4711	0.2874	0.087*
C19	0.4543 (10)	0.1351 (10)	0.36401 (13)	0.093 (3)
H19A	0.5087	0.0572	0.3729	0.140*
H19B	0.5393	0.2095	0.3607	0.140*
H19C	0.4085	0.0986	0.3488	0.140*
C20	−0.0234 (8)	0.6875 (6)	0.28960 (9)	0.0500 (13)
C21	0.0543 (13)	0.8169 (8)	0.27881 (12)	0.092 (3)
H21A	0.0089	0.9039	0.2866	0.110*
H21B	0.1805	0.8153	0.2807	0.110*
C22	−0.1130 (8)	0.6210 (6)	0.27234 (9)	0.0518 (14)
H22	−0.1806	0.5379	0.2746	0.062*
C23	−0.0906 (7)	0.6964 (6)	0.24926 (10)	0.0483 (13)
C24	0.2124 (7)	0.0798 (6)	0.46657 (9)	0.0466 (13)
H24	0.1133	0.1360	0.4729	0.056*
C25	0.2076 (8)	−0.0721 (7)	0.47802 (10)	0.0573 (16)
H25	0.2134	−0.0593	0.4959	0.069*
C26	0.3627 (8)	−0.1593 (6)	0.47073 (9)	0.0520 (14)
H26	0.3575	−0.1784	0.4530	0.062*
C27	0.5305 (8)	−0.0755 (7)	0.47648 (11)	0.0586 (15)
H27	0.5420	−0.0666	0.4944	0.070*
C28	0.5231 (8)	0.0761 (7)	0.46538 (10)	0.0585 (15)
H28	0.5199	0.0672	0.4474	0.070*
C29	0.6776 (11)	0.1705 (10)	0.47244 (18)	0.100 (3)
H29A	0.6665	0.2639	0.4647	0.150*
H29B	0.7840	0.1249	0.4671	0.150*
H29C	0.6802	0.1825	0.4900	0.150*
C30	0.3557 (13)	−0.4182 (8)	0.46882 (13)	0.089 (2)
H30A	0.3545	−0.5033	0.4790	0.133*
H30B	0.4570	−0.4203	0.4584	0.133*
H30C	0.2520	−0.4163	0.4589	0.133*
C31	0.8192 (19)	0.6822 (11)	0.42095 (19)	0.139 (5)
H31A	0.8183	0.7638	0.4325	0.166*	0.491 (8)
H31B	0.8096	0.7299	0.4366	0.166*	0.509 (8)
C32	0.4957 (9)	0.5222 (8)	0.21599 (13)	0.0735 (18)
H32	0.6136	0.5642	0.2159	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.242 (6)	0.276 (7)	0.211 (5)	0.036 (6)	−0.013 (4)	0.001 (5)
Cl2A	0.169 (5)	0.071 (3)	0.199 (6)	−0.009 (3)	0.078 (5)	0.011 (3)
Cl2B	0.169 (5)	0.071 (3)	0.199 (6)	−0.009 (3)	0.078 (5)	0.011 (3)
Cl3	0.205 (3)	0.0919 (16)	0.0998 (15)	−0.0363 (19)	0.0438 (18)	−0.0002 (13)
Cl4	0.145 (2)	0.254 (4)	0.0746 (14)	−0.046 (3)	0.0186 (15)	0.0260 (19)
Cl5	0.1096 (18)	0.1063 (17)	0.177 (3)	0.0440 (16)	−0.0319 (18)	−0.0303 (18)
Cl6	0.150 (2)	0.0930 (15)	0.0995 (14)	0.0094 (16)	−0.0088 (15)	−0.0165 (12)
O1	0.112 (4)	0.076 (3)	0.053 (2)	−0.039 (3)	−0.028 (2)	0.033 (2)
O2	0.064 (2)	0.047 (2)	0.0341 (17)	0.0096 (19)	−0.0001 (16)	0.0101 (16)
O3	0.062 (2)	0.051 (2)	0.050 (2)	0.001 (2)	−0.0090 (19)	−0.0002 (18)
O4	0.093 (3)	0.071 (3)	0.037 (2)	−0.007 (3)	−0.016 (2)	0.0069 (19)
O5	0.061 (2)	0.053 (2)	0.0368 (17)	−0.014 (2)	−0.0098 (16)	0.0023 (17)
O6	0.074 (3)	0.100 (4)	0.103 (4)	−0.023 (3)	−0.020 (3)	0.043 (3)
O7	0.131 (4)	0.049 (2)	0.060 (2)	0.002 (3)	−0.037 (3)	0.009 (2)
O8	0.066 (3)	0.110 (4)	0.119 (5)	0.028 (3)	−0.014 (3)	−0.033 (4)
C1	0.059 (4)	0.075 (4)	0.062 (4)	−0.019 (3)	−0.020 (3)	0.034 (3)
C2	0.114 (6)	0.044 (3)	0.048 (3)	−0.004 (4)	−0.024 (4)	−0.001 (3)
C3	0.073 (4)	0.055 (3)	0.037 (3)	0.018 (3)	0.007 (3)	0.010 (2)
C4	0.049 (3)	0.051 (3)	0.058 (3)	−0.008 (3)	−0.007 (3)	0.021 (3)
C5	0.077 (4)	0.047 (3)	0.032 (2)	0.000 (3)	−0.006 (3)	0.008 (2)
C6	0.153 (7)	0.043 (3)	0.052 (3)	−0.024 (4)	−0.025 (4)	0.008 (3)
C7	0.126 (6)	0.056 (4)	0.052 (3)	−0.039 (4)	−0.034 (4)	0.014 (3)
C8	0.056 (3)	0.047 (3)	0.032 (2)	−0.005 (3)	0.003 (2)	0.002 (2)
C9	0.052 (3)	0.044 (3)	0.031 (2)	−0.003 (2)	−0.003 (2)	0.006 (2)
C10	0.058 (3)	0.055 (3)	0.037 (3)	0.003 (3)	0.003 (2)	0.014 (2)
C11	0.060 (4)	0.071 (4)	0.053 (3)	−0.023 (3)	−0.019 (3)	0.022 (3)
C12	0.084 (4)	0.047 (3)	0.049 (3)	−0.021 (3)	−0.016 (3)	0.012 (3)
C13	0.062 (3)	0.041 (3)	0.025 (2)	−0.005 (3)	−0.003 (2)	0.005 (2)
C14	0.055 (3)	0.041 (3)	0.025 (2)	−0.006 (2)	0.001 (2)	−0.0015 (19)
C15	0.055 (3)	0.089 (5)	0.044 (3)	0.011 (4)	0.012 (3)	0.016 (3)
C16	0.103 (6)	0.088 (5)	0.058 (4)	0.043 (5)	0.022 (4)	0.018 (4)
C17	0.088 (4)	0.040 (3)	0.034 (2)	0.008 (3)	−0.005 (3)	0.002 (2)
C18	0.065 (4)	0.065 (4)	0.043 (3)	−0.009 (3)	0.003 (3)	0.016 (3)
C19	0.087 (5)	0.108 (6)	0.085 (5)	0.039 (5)	0.028 (4)	0.044 (5)
C20	0.063 (4)	0.044 (3)	0.043 (3)	0.002 (3)	−0.004 (3)	0.003 (2)
C21	0.138 (7)	0.073 (5)	0.063 (4)	−0.048 (5)	−0.036 (4)	0.021 (4)
C22	0.066 (4)	0.039 (3)	0.051 (3)	−0.001 (3)	−0.004 (3)	0.010 (2)
C23	0.058 (3)	0.042 (3)	0.045 (3)	−0.002 (3)	−0.003 (3)	0.009 (2)
C24	0.054 (3)	0.052 (3)	0.034 (2)	0.001 (3)	0.004 (2)	0.007 (2)
C25	0.066 (4)	0.066 (4)	0.039 (3)	−0.003 (3)	−0.005 (3)	0.023 (3)
C26	0.073 (4)	0.049 (3)	0.033 (2)	0.001 (3)	−0.014 (3)	0.008 (2)
C27	0.055 (4)	0.070 (4)	0.050 (3)	0.013 (3)	−0.011 (3)	−0.006 (3)
C28	0.056 (4)	0.077 (4)	0.043 (3)	0.004 (3)	−0.005 (3)	0.004 (3)
C29	0.072 (5)	0.095 (6)	0.133 (7)	−0.013 (5)	−0.015 (5)	0.019 (6)
C30	0.131 (7)	0.057 (4)	0.079 (5)	0.000 (5)	−0.009 (5)	0.007 (4)
C31	0.233 (14)	0.084 (6)	0.099 (6)	0.062 (8)	0.070 (8)	0.028 (5)
C32	0.057 (4)	0.072 (4)	0.091 (5)	0.008 (4)	−0.008 (4)	−0.003 (4)

Geometric parameters (Å, º)

Cl1—C31	1.671 (13)	C11—C12	1.518 (9)
Cl2A—C31	1.785 (11)	C11—H11A	0.97
Cl2B—C31	1.820 (13)	C11—H11B	0.97
Cl3—C31	1.718 (13)	C12—C13	1.554 (7)
Cl4—C32	1.720 (8)	C12—H12A	0.97
Cl5—C32	1.732 (7)	C12—H12B	0.97
Cl6—C32	1.765 (7)	C13—C18	1.534 (8)
O1—C23	1.329 (7)	C13—C14	1.544 (7)
O1—C21	1.439 (7)	C13—C17	1.576 (8)
O2—C24	1.398 (6)	C14—C15	1.537 (8)
O2—C3	1.426 (6)	C15—C16	1.534 (9)
O3—C24	1.403 (7)	C15—H15A	0.97
O3—C28	1.433 (7)	C15—H15B	0.97
O4—C23	1.213 (6)	C16—C17	1.534 (10)
O5—C14	1.430 (5)	C16—H16A	0.97
O5—H5O	0.82	C16—H16B	0.97
O6—C25	1.405 (8)	C17—C20	1.530 (7)
O6—H6O	0.82	C17—H17	0.98
O7—C30	1.394 (8)	C18—H18A	0.96
O7—C26	1.423 (7)	C18—H18B	0.96
O8—C27	1.399 (8)	C18—H18C	0.96
O8—H8O	0.82	C19—H19A	0.96
C1—C10	1.514 (8)	C19—H19B	0.96
C1—C2	1.519 (9)	C19—H19C	0.96
C1—H1A	0.97	C20—C22	1.313 (7)
C1—H1B	0.97	C20—C21	1.453 (9)
C2—C3	1.519 (9)	C21—H21A	0.97
C2—H2A	0.97	C21—H21B	0.97
C2—H2B	0.97	C22—C23	1.444 (7)
C3—C4	1.518 (8)	C22—H22	0.93
C3—H3	0.98	C24—C25	1.529 (8)
C4—C5	1.523 (8)	C24—H24	0.98
C4—H4A	0.97	C25—C26	1.486 (9)
C4—H4B	0.97	C25—H25	0.98
C5—C6	1.516 (8)	C26—C27	1.528 (9)
C5—C10	1.541 (8)	C26—H26	0.98
C5—H5	0.98	C27—C28	1.519 (9)
C6—C7	1.529 (9)	C27—H27	0.98
C6—H6A	0.97	C28—C29	1.515 (10)
C6—H6B	0.97	C28—H28	0.98
C7—C8	1.532 (8)	C29—H29A	0.96
C7—H7A	0.97	C29—H29B	0.96
C7—H7B	0.97	C29—H29C	0.96
C8—C14	1.522 (7)	C30—H30A	0.96
C8—C9	1.547 (7)	C30—H30B	0.96
C8—H8	0.98	C30—H30C	0.96
C9—C11	1.511 (8)	C31—H31A	0.98
C9—C10	1.557 (7)	C31—H31B	0.96
C9—H9	0.98	C32—H32	0.98
C10—C19	1.545 (9)
C23—O1—C21	108.2 (4)	C15—C16—H16A	110.3
C24—O2—C3	115.7 (4)	C17—C16—H16B	110.3
C24—O3—C28	113.8 (4)	C15—C16—H16B	110.3
C14—O5—H5O	109.5	H16A—C16—H16B	108.5
C25—O6—H6O	109.5	C20—C17—C16	113.2 (5)
C30—O7—C26	115.5 (4)	C20—C17—C13	114.5 (4)
C27—O8—H8O	109.5	C16—C17—C13	105.7 (4)
C10—C1—C2	115.4 (5)	C20—C17—H17	107.7
C10—C1—H1A	108.4	C16—C17—H17	107.7
C2—C1—H1A	108.4	C13—C17—H17	107.7
C10—C1—H1B	108.4	C13—C18—H18A	109.5
C2—C1—H1B	108.4	C13—C18—H18B	109.5
H1A—C1—H1B	107.5	H18A—C18—H18B	109.5
C3—C2—C1	111.3 (5)	C13—C18—H18C	109.5
C3—C2—H2A	109.4	H18A—C18—H18C	109.5
C1—C2—H2A	109.4	H18B—C18—H18C	109.5
C3—C2—H2B	109.4	C10—C19—H19A	109.5
C1—C2—H2B	109.4	C10—C19—H19B	109.5
H2A—C2—H2B	108.0	H19A—C19—H19B	109.5
O2—C3—C4	107.6 (5)	C10—C19—H19C	109.5
O2—C3—C2	111.8 (5)	H19A—C19—H19C	109.5
C4—C3—C2	110.9 (4)	H19B—C19—H19C	109.5
O2—C3—H3	108.8	C22—C20—C21	107.8 (5)
C4—C3—H3	108.8	C22—C20—C17	131.9 (5)
C2—C3—H3	108.8	C21—C20—C17	120.2 (5)
C3—C4—C5	114.5 (5)	O1—C21—C20	105.8 (5)
C3—C4—H4A	108.6	O1—C21—H21A	110.6
C5—C4—H4A	108.6	C20—C21—H21A	110.6
C3—C4—H4B	108.6	O1—C21—H21B	110.6
C5—C4—H4B	108.6	C20—C21—H21B	110.6
H4A—C4—H4B	107.6	H21A—C21—H21B	108.7
C6—C5—C4	111.5 (6)	C20—C22—C23	109.6 (5)
C6—C5—C10	112.1 (4)	C20—C22—H22	125.2
C4—C5—C10	112.3 (5)	C23—C22—H22	125.2
C6—C5—H5	106.8	O4—C23—O1	120.4 (5)
C4—C5—H5	106.8	O4—C23—C22	131.1 (5)
C10—C5—H5	106.8	O1—C23—C22	108.5 (5)
C5—C6—C7	112.2 (5)	O2—C24—O3	113.7 (4)
C5—C6—H6A	109.2	O2—C24—C25	107.6 (5)
C7—C6—H6A	109.2	O3—C24—C25	109.5 (4)
C5—C6—H6B	109.2	O2—C24—H24	108.7
C7—C6—H6B	109.2	O3—C24—H24	108.7
H6A—C6—H6B	107.9	C25—C24—H24	108.7
C6—C7—C8	112.2 (6)	O6—C25—C26	113.8 (6)
C6—C7—H7A	109.2	O6—C25—C24	110.2 (5)
C8—C7—H7A	109.2	C26—C25—C24	111.4 (5)
C6—C7—H7B	109.2	O6—C25—H25	107.0
C8—C7—H7B	109.2	C26—C25—H25	107.0
H7A—C7—H7B	107.9	C24—C25—H25	107.0
C14—C8—C7	111.7 (5)	O7—C26—C25	109.4 (5)
C14—C8—C9	113.4 (4)	O7—C26—C27	110.3 (5)
C7—C8—C9	112.6 (4)	C25—C26—C27	110.0 (5)
C14—C8—H8	106.1	O7—C26—H26	109.0
C7—C8—H8	106.1	C25—C26—H26	109.0
C9—C8—H8	106.1	C27—C26—H26	109.0
C11—C9—C8	109.8 (4)	O8—C27—C28	112.8 (6)
C11—C9—C10	114.9 (4)	O8—C27—C26	107.3 (5)
C8—C9—C10	112.9 (4)	C28—C27—C26	110.5 (5)
C11—C9—H9	106.2	O8—C27—H27	108.7
C8—C9—H9	106.2	C28—C27—H27	108.7
C10—C9—H9	106.2	C26—C27—H27	108.7
C1—C10—C5	107.8 (4)	O3—C28—C29	107.2 (6)
C1—C10—C19	105.9 (5)	O3—C28—C27	110.2 (5)
C5—C10—C19	110.2 (5)	C29—C28—C27	113.4 (5)
C1—C10—C9	113.0 (5)	O3—C28—H28	108.7
C5—C10—C9	109.6 (4)	C29—C28—H28	108.7
C19—C10—C9	110.3 (4)	C27—C28—H28	108.7
C9—C11—C12	112.1 (5)	C28—C29—H29A	109.5
C9—C11—H11A	109.2	C28—C29—H29B	109.5
C12—C11—H11A	109.2	H29A—C29—H29B	109.5
C9—C11—H11B	109.2	C28—C29—H29C	109.5
C12—C11—H11B	109.2	H29A—C29—H29C	109.5
H11A—C11—H11B	107.9	H29B—C29—H29C	109.5
C11—C12—C13	113.3 (5)	O7—C30—H30A	109.5
C11—C12—H12A	108.9	O7—C30—H30B	109.5
C13—C12—H12A	108.9	H30A—C30—H30B	109.5
C11—C12—H12B	108.9	O7—C30—H30C	109.5
C13—C12—H12B	108.9	H30A—C30—H30C	109.5
H12A—C12—H12B	107.7	H30B—C30—H30C	109.5
C18—C13—C14	113.0 (4)	Cl1—C31—Cl3	112.3 (5)
C18—C13—C12	109.5 (5)	Cl1—C31—Cl2A	132.1 (10)
C14—C13—C12	108.5 (4)	Cl3—C31—Cl2A	105.6 (7)
C18—C13—C17	114.7 (4)	Cl1—C31—Cl2B	98.3 (9)
C14—C13—C17	104.1 (4)	Cl3—C31—Cl2B	109.9 (6)
C12—C13—C17	106.7 (4)	Cl1—C31—H31A	100.4
O5—C14—C8	110.9 (4)	Cl3—C31—H31A	100.4
O5—C14—C15	103.4 (4)	Cl2A—C31—H31A	100.4
C8—C14—C15	114.3 (4)	Cl2B—C31—H31A	134.7
O5—C14—C13	109.2 (3)	Cl1—C31—H31B	111.8
C8—C14—C13	115.1 (4)	Cl3—C31—H31B	111.9
C15—C14—C13	103.0 (4)	Cl2A—C31—H31B	78.1
C16—C15—C14	105.1 (4)	Cl2B—C31—H31B	112.0
C16—C15—H15A	110.7	Cl4—C32—Cl5	116.3 (4)
C14—C15—H15A	110.7	Cl4—C32—Cl6	108.2 (4)
C16—C15—H15B	110.7	Cl5—C32—Cl6	107.1 (4)
C14—C15—H15B	110.7	Cl4—C32—H32	108.3
H15A—C15—H15B	108.8	Cl5—C32—H32	108.3
C17—C16—C15	107.1 (5)	Cl6—C32—H32	108.3
C17—C16—H16A	110.3
C10—C1—C2—C3	55.6 (7)	C12—C13—C14—C15	76.4 (5)
C24—O2—C3—C4	−156.0 (4)	C17—C13—C14—C15	−36.9 (4)
C24—O2—C3—C2	82.0 (6)	O5—C14—C15—C16	−76.0 (6)
C1—C2—C3—O2	70.0 (6)	C8—C14—C15—C16	163.3 (5)
C1—C2—C3—C4	−50.2 (6)	C13—C14—C15—C16	37.7 (6)
O2—C3—C4—C5	−71.5 (6)	C14—C15—C16—C17	−23.7 (7)
C2—C3—C4—C5	51.0 (6)	C15—C16—C17—C20	126.6 (5)
C3—C4—C5—C6	179.7 (5)	C15—C16—C17—C13	0.5 (7)
C3—C4—C5—C10	−53.5 (6)	C18—C13—C17—C20	21.3 (7)
C4—C5—C6—C7	69.7 (8)	C14—C13—C17—C20	−102.6 (5)
C10—C5—C6—C7	−57.1 (8)	C12—C13—C17—C20	142.7 (5)
C5—C6—C7—C8	53.4 (8)	C18—C13—C17—C16	146.6 (5)
C6—C7—C8—C14	−179.0 (5)	C14—C13—C17—C16	22.6 (6)
C6—C7—C8—C9	−50.0 (7)	C12—C13—C17—C16	−92.0 (6)
C14—C8—C9—C11	−51.6 (6)	C16—C17—C20—C22	−42.9 (9)
C7—C8—C9—C11	−179.8 (6)	C13—C17—C20—C22	78.3 (8)
C14—C8—C9—C10	178.8 (4)	C16—C17—C20—C21	133.9 (7)
C7—C8—C9—C10	50.6 (7)	C13—C17—C20—C21	−104.9 (7)
C2—C1—C10—C5	−55.5 (7)	C23—O1—C21—C20	1.0 (9)
C2—C1—C10—C19	−173.5 (5)	C22—C20—C21—O1	−2.8 (9)
C2—C1—C10—C9	65.7 (6)	C17—C20—C21—O1	179.7 (6)
C6—C5—C10—C1	179.3 (6)	C21—C20—C22—C23	3.5 (8)
C4—C5—C10—C1	52.8 (6)	C17—C20—C22—C23	−179.4 (6)
C6—C5—C10—C19	−65.6 (7)	C21—O1—C23—O4	179.8 (7)
C4—C5—C10—C19	168.0 (5)	C21—O1—C23—C22	1.1 (8)
C6—C5—C10—C9	56.0 (7)	C20—C22—C23—O4	178.5 (6)
C4—C5—C10—C9	−70.5 (5)	C20—C22—C23—O1	−3.0 (7)
C11—C9—C10—C1	60.2 (6)	C3—O2—C24—O3	−84.3 (6)
C8—C9—C10—C1	−172.9 (5)	C3—O2—C24—C25	154.2 (5)
C11—C9—C10—C5	−179.6 (5)	C28—O3—C24—O2	−59.9 (6)
C8—C9—C10—C5	−52.7 (6)	C28—O3—C24—C25	60.5 (5)
C11—C9—C10—C19	−58.1 (7)	O2—C24—C25—O6	−60.1 (6)
C8—C9—C10—C19	68.8 (7)	O3—C24—C25—O6	175.9 (5)
C8—C9—C11—C12	55.9 (6)	O2—C24—C25—C26	67.2 (6)
C10—C9—C11—C12	−175.6 (5)	O3—C24—C25—C26	−56.8 (6)
C9—C11—C12—C13	−58.9 (7)	C30—O7—C26—C25	120.2 (7)
C11—C12—C13—C18	−71.1 (6)	C30—O7—C26—C27	−118.6 (7)
C11—C12—C13—C14	52.6 (7)	O6—C25—C26—O7	−60.1 (6)
C11—C12—C13—C17	164.3 (5)	C24—C25—C26—O7	174.6 (4)
C7—C8—C14—O5	−56.7 (6)	O6—C25—C26—C27	178.6 (5)
C9—C8—C14—O5	174.7 (4)	C24—C25—C26—C27	53.3 (6)
C7—C8—C14—C15	59.8 (6)	O7—C26—C27—O8	63.6 (6)
C9—C8—C14—C15	−68.9 (6)	C25—C26—C27—O8	−175.6 (5)
C7—C8—C14—C13	178.7 (4)	O7—C26—C27—C28	−173.1 (5)
C9—C8—C14—C13	50.1 (6)	C25—C26—C27—C28	−52.2 (6)
C18—C13—C14—O5	−52.6 (6)	C24—O3—C28—C29	176.0 (5)
C12—C13—C14—O5	−174.2 (5)	C24—O3—C28—C27	−60.2 (5)
C17—C13—C14—O5	72.5 (5)	O8—C27—C28—O3	174.4 (5)
C18—C13—C14—C8	73.0 (5)	C26—C27—C28—O3	54.3 (6)
C12—C13—C14—C8	−48.6 (6)	O8—C27—C28—C29	−65.4 (7)
C17—C13—C14—C8	−162.0 (4)	C26—C27—C28—C29	174.4 (6)
C18—C13—C14—C15	−162.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···O4^i	0.82	2.22	2.967 (5)	151
O5—H5O···O1^i	0.82	2.71	3.294 (5)	129
O6—H6O···O7	0.82	2.77	2.848 (8)	87
O8—H8O···O6^ii	0.82	2.62	2.896 (8)	101
C2—H2A···O3	0.97	2.52	3.176 (7)	125
C7—H7B···O5	0.97	2.58	2.912 (7)	100
C18—H18C···O5	0.96	2.56	2.887 (7)	100
C32—H32···O4^ii	0.98	2.19	3.133 (8)	160

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