(+)-(1S,2S,4S,4aR,5R,6S,9S,10S)-4-Benzyl­oxy-9,10-(carbonyl­dioxy)-1-methoxy­methoxy-4a,6,8,8-tetra­methyl-7-methyl­enedodeca­hydro-6,9-ethano­benzo­cyclo­octene-5-ol

The title tetracyclic compound, C₂₉H₄₀O₇, has been obtained unexpectedly in a synthetic study of the natural diterpenoid, paclitaxel. There is an intramolecular O—H...O hydrogen bond between the hydroxy and benzyl­oxy groups.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.126
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C29
PLAT410_ALERT_2_C Short Intra H...H Contact  H14A   ..  H21      =       1.96 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H10    ..  H27C     =       1.80 Ang.

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           27.50
           From the CIF: _reflns_number_total               3419
           Count of symmetry unique reflns         3425
           Completeness (_total/calc)             99.82%
           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

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

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

---

Computing details

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C29H40O7	Dx = 1.260 Mg m^−3
Mr = 500.63	Melting point = 427–430 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
a = 13.754 (2) Å	Cell parameters from 25 reflections
b = 21.026 (7) Å	θ = 10.0–11.2°
c = 9.1287 (10) Å	µ = 0.09 mm^−1
V = 2639.9 (10) Å^3	T = 297 K
Z = 4	Prismatic, colourless
F(000) = 1080	0.50 × 0.40 × 0.40 mm

Data collection

Rigaku AFC7R diffractometer	θmax = 27.5°
ω scans	h = −7→17
4059 measured reflections	k = 0→27
3419 independent reflections	l = −11→4
2443 reflections with I > 2σ(I)	3 standard reflections every 150 reflections
Rint = 0.016	intensity decay: 0.8%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0632P)^2 + 0.271P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.126	(Δ/σ)max = 0.002
S = 1.02	Δρmax = 0.20 e Å^−3
3419 reflections	Δρmin = −0.17 e Å^−3
326 parameters	Absolute structure: see text

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4180 (2)	0.2820 (1)	0.3995 (3)	0.0664 (6)
O2	0.4702 (2)	0.1833 (1)	0.3851 (2)	0.0613 (6)
O3	0.3901 (2)	0.2148 (2)	0.5844 (3)	0.0860 (8)
O4	0.6455 (2)	0.2327 (1)	−0.1698 (3)	0.0588 (6)
O5	0.5992 (1)	0.10974 (9)	−0.2254 (2)	0.0433 (4)
O6	0.3386 (1)	0.11548 (9)	0.2367 (2)	0.0520 (5)
O7	0.2929 (2)	0.0140 (1)	0.3211 (3)	0.0724 (7)
C8	0.4230 (3)	0.2259 (2)	0.4671 (4)	0.0622 (8)
C9	0.4620 (2)	0.2795 (1)	0.2537 (3)	0.0491 (6)
C10	0.4998 (2)	0.2098 (1)	0.2455 (3)	0.0443 (6)
C11	0.5534 (2)	0.2293 (1)	−0.0973 (3)	0.0424 (6)
C12	0.5327 (2)	0.2977 (1)	−0.0357 (3)	0.0468 (6)
C13	0.4212 (2)	0.3063 (1)	−0.0075 (4)	0.0540 (7)
C14	0.3824 (2)	0.2948 (1)	0.1479 (4)	0.0530 (7)
C15	0.5961 (2)	0.3157 (1)	0.0968 (4)	0.0530 (7)
C16	0.5471 (2)	0.3270 (2)	0.2451 (4)	0.0627 (8)
C17	0.5548 (3)	0.3438 (2)	−0.1628 (4)	0.0699 (10)
C18	0.6917 (2)	0.3225 (2)	0.0812 (5)	0.079 (1)
C19	0.5090 (3)	0.3966 (2)	0.2480 (6)	0.091 (1)
C20	0.6153 (3)	0.3187 (3)	0.3753 (5)	0.095 (1)
C21	0.4679 (2)	0.1678 (1)	0.1152 (3)	0.0363 (5)
C22	0.4318 (2)	0.1025 (1)	0.1712 (3)	0.0437 (6)
C23	0.4185 (2)	0.0534 (1)	0.0515 (3)	0.0488 (7)
C24	0.5082 (2)	0.0492 (1)	−0.0441 (3)	0.0477 (6)
C25	0.5237 (2)	0.1131 (1)	−0.1149 (3)	0.0399 (5)
C26	0.5502 (2)	0.1660 (1)	−0.0034 (3)	0.0368 (5)
C27	0.6497 (2)	0.1502 (2)	0.0652 (3)	0.0487 (7)
C28	0.5638 (2)	0.0862 (2)	−0.3620 (3)	0.0586 (8)
C29	0.6463 (2)	0.0791 (1)	−0.4679 (3)	0.0477 (6)
C30	0.6585 (3)	0.0233 (2)	−0.5438 (4)	0.0707 (10)
C31	0.7316 (4)	0.0159 (2)	−0.6453 (5)	0.088 (1)
C32	0.7953 (3)	0.0644 (2)	−0.6707 (4)	0.077 (1)
C33	0.7848 (3)	0.1201 (2)	−0.5976 (4)	0.078 (1)
C34	0.7105 (3)	0.1276 (2)	−0.4969 (4)	0.0647 (9)
C35	0.3150 (3)	0.0771 (2)	0.3575 (4)	0.0696 (10)
C36	0.2085 (3)	0.0077 (2)	0.2331 (6)	0.085 (1)
H4	0.6572	0.1986	−0.2095	0.0588*
H10	0.5689	0.2115	0.2450	0.0530*
H11	0.5072	0.2231	−0.1732	0.0502*
H13A	0.4053	0.3489	−0.0331	0.0641*
H13B	0.3882	0.2778	−0.0708	0.0641*
H14A	0.3378	0.2603	0.1455	0.0626*
H14B	0.3498	0.3321	0.1805	0.0626*
H17A	0.6221	0.3415	−0.1866	0.0835*
H17B	0.5173	0.3322	−0.2459	0.0835*
H17C	0.5390	0.3859	−0.1340	0.0835*
H18A	0.7305	0.3345	0.1631	0.0949*
H18B	0.7214	0.3153	−0.0111	0.0949*
H19A	0.5618	0.4250	0.2331	0.1083*
H19B	0.4625	0.4022	0.1722	0.1083*
H19C	0.4797	0.4050	0.3400	0.1083*
H20A	0.6414	0.2768	0.3748	0.1136*
H20B	0.6669	0.3486	0.3692	0.1136*
H20C	0.5803	0.3252	0.4640	0.1136*
H21	0.4136	0.1882	0.0716	0.0430*
H22	0.4753	0.0868	0.2436	0.0522*
H23A	0.4070	0.0131	0.0951	0.0582*
H23B	0.3646	0.0650	−0.0074	0.0582*
H24A	0.5632	0.0382	0.0138	0.0570*
H24B	0.4990	0.0176	−0.1176	0.0570*
H25	0.4649	0.1249	−0.1617	0.0480*
H27A	0.6458	0.1104	0.1144	0.0580*
H27B	0.6975	0.1479	−0.0095	0.0580*
H27C	0.6669	0.1824	0.1333	0.0580*
H28A	0.5336	0.0461	−0.3473	0.0701*
H28B	0.5175	0.1153	−0.4008	0.0701*
H30	0.6154	−0.0112	−0.5254	0.0844*
H31	0.7375	−0.0228	−0.6982	0.1046*
H32	0.8471	0.0590	−0.7387	0.0920*
H33	0.8286	0.1540	−0.6154	0.0932*
H34	0.7037	0.1670	−0.4468	0.0776*
H35A	0.3690	0.0769	0.4228	0.0828*
H35B	0.2603	0.0951	0.4054	0.0828*
H36A	0.1538	0.0239	0.2848	0.1031*
H36B	0.2169	0.0311	0.1449	0.1031*
H36C	0.1981	−0.0358	0.2106	0.1031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.074 (1)	0.068 (1)	0.057 (1)	0.007 (1)	0.023 (1)	−0.014 (1)
O2	0.081 (1)	0.071 (1)	0.0322 (10)	0.016 (1)	−0.003 (1)	−0.0019 (10)
O3	0.093 (2)	0.119 (2)	0.046 (1)	0.011 (2)	0.014 (1)	−0.003 (1)
O4	0.057 (1)	0.057 (1)	0.063 (1)	−0.010 (1)	0.026 (1)	−0.008 (1)
O5	0.0407 (9)	0.057 (1)	0.0327 (9)	0.0016 (8)	0.0008 (8)	−0.0063 (8)
O6	0.051 (1)	0.058 (1)	0.048 (1)	0.0045 (9)	0.0155 (10)	0.0086 (10)
O7	0.075 (2)	0.067 (2)	0.075 (2)	0.002 (1)	0.013 (1)	0.028 (1)
C8	0.065 (2)	0.080 (2)	0.041 (2)	0.006 (2)	0.003 (2)	−0.010 (2)
C9	0.047 (1)	0.054 (2)	0.046 (1)	0.001 (1)	0.010 (1)	−0.014 (1)
C10	0.039 (1)	0.060 (2)	0.034 (1)	0.003 (1)	−0.001 (1)	−0.006 (1)
C11	0.039 (1)	0.048 (1)	0.040 (1)	−0.005 (1)	0.000 (1)	0.000 (1)
C12	0.047 (1)	0.044 (1)	0.050 (2)	−0.002 (1)	0.005 (1)	0.001 (1)
C13	0.049 (2)	0.048 (2)	0.065 (2)	0.007 (1)	−0.002 (2)	0.006 (1)
C14	0.043 (1)	0.044 (1)	0.072 (2)	0.006 (1)	0.008 (1)	−0.002 (1)
C15	0.047 (2)	0.049 (2)	0.063 (2)	−0.008 (1)	0.006 (1)	−0.014 (1)
C16	0.060 (2)	0.063 (2)	0.065 (2)	−0.013 (2)	0.006 (2)	−0.023 (2)
C17	0.084 (2)	0.054 (2)	0.072 (2)	−0.005 (2)	0.019 (2)	0.011 (2)
C18	0.049 (2)	0.099 (3)	0.090 (3)	−0.023 (2)	0.009 (2)	−0.034 (2)
C19	0.096 (3)	0.059 (2)	0.118 (3)	−0.017 (2)	0.036 (3)	−0.036 (2)
C20	0.084 (3)	0.132 (4)	0.069 (2)	−0.033 (3)	−0.009 (2)	−0.033 (3)
C21	0.033 (1)	0.043 (1)	0.033 (1)	0.007 (1)	−0.002 (1)	−0.001 (1)
C22	0.045 (1)	0.050 (1)	0.037 (1)	0.004 (1)	0.003 (1)	0.008 (1)
C23	0.056 (2)	0.042 (1)	0.049 (2)	−0.002 (1)	0.009 (1)	0.002 (1)
C24	0.054 (2)	0.041 (1)	0.048 (2)	0.003 (1)	0.005 (1)	−0.003 (1)
C25	0.037 (1)	0.047 (1)	0.035 (1)	0.004 (1)	0.002 (1)	−0.001 (1)
C26	0.032 (1)	0.045 (1)	0.034 (1)	0.0021 (10)	−0.001 (1)	−0.002 (1)
C27	0.037 (1)	0.067 (2)	0.043 (1)	0.008 (1)	−0.004 (1)	−0.008 (1)
C28	0.057 (2)	0.081 (2)	0.037 (1)	−0.004 (2)	−0.004 (1)	−0.009 (1)
C29	0.050 (1)	0.062 (2)	0.031 (1)	0.006 (1)	−0.006 (1)	−0.003 (1)
C30	0.105 (3)	0.054 (2)	0.053 (2)	0.002 (2)	0.013 (2)	−0.003 (2)
C31	0.128 (4)	0.072 (3)	0.062 (2)	0.036 (3)	0.022 (3)	−0.010 (2)
C32	0.067 (2)	0.113 (3)	0.051 (2)	0.029 (2)	0.005 (2)	−0.003 (2)
C33	0.065 (2)	0.121 (3)	0.049 (2)	−0.025 (2)	0.001 (2)	−0.012 (2)
C34	0.076 (2)	0.073 (2)	0.046 (2)	−0.012 (2)	0.009 (2)	−0.017 (2)
C35	0.071 (2)	0.090 (3)	0.047 (2)	−0.003 (2)	0.016 (2)	0.013 (2)
C36	0.082 (3)	0.084 (3)	0.090 (3)	−0.020 (2)	0.016 (3)	0.019 (2)

Geometric parameters (Å, º)

O1—C8	1.333 (4)	C19—H19C	0.949
O1—C9	1.462 (4)	C20—H20A	0.952
O2—C8	1.334 (4)	C20—H20B	0.949
O2—C10	1.449 (4)	C20—H20C	0.951
O3—C8	1.186 (4)	C21—C22	1.545 (4)
O4—C11	1.431 (3)	C21—C26	1.567 (3)
O4—H4	0.820	C21—H21	0.950
O5—C25	1.449 (3)	C22—C23	1.515 (4)
O5—C28	1.427 (4)	C22—H22	0.951
O6—C22	1.441 (3)	C23—C24	1.514 (4)
O6—C35	1.405 (4)	C23—H23A	0.948
O7—C35	1.400 (5)	C23—H23B	0.948
O7—C36	1.418 (5)	C24—C25	1.507 (4)
C9—C10	1.556 (4)	C24—H24A	0.950
C9—C14	1.495 (4)	C24—H24B	0.952
C9—C16	1.542 (4)	C25—C26	1.552 (4)
C10—C21	1.545 (4)	C25—H25	0.948
C10—H10	0.951	C26—C27	1.542 (4)
C11—C12	1.571 (4)	C27—H27A	0.950
C11—C26	1.582 (4)	C27—H27B	0.948
C11—H11	0.949	C27—H27C	0.950
C12—C13	1.566 (4)	C28—C29	1.498 (4)
C12—C15	1.538 (4)	C28—H28A	0.950
C12—C17	1.542 (5)	C28—H28B	0.951
C13—C14	1.535 (5)	C29—C30	1.374 (4)
C13—H13A	0.950	C29—C34	1.375 (5)
C13—H13B	0.948	C30—C31	1.376 (6)
C14—H14A	0.950	C30—H30	0.951
C14—H14B	0.950	C31—C32	1.363 (7)
C15—C16	1.531 (5)	C31—H31	0.951
C15—C18	1.331 (4)	C32—C33	1.356 (7)
C16—C19	1.554 (5)	C32—H32	0.952
C16—C20	1.525 (6)	C33—C34	1.384 (5)
C17—H17A	0.951	C33—H33	0.948
C17—H17B	0.949	C34—H34	0.949
C17—H17C	0.950	C35—H35A	0.952
C18—H18A	0.952	C35—H35B	0.949
C18—H18B	0.948	C36—H36A	0.951
C19—H19A	0.950	C36—H36B	0.950
C19—H19B	0.950	C36—H36C	0.950
C8—O1—C9	111.6 (2)	C10—C21—H21	106.7
C8—O2—C10	111.8 (2)	C22—C21—C26	116.1 (2)
C11—O4—H4	109.5	C22—C21—H21	106.7
C25—O5—C28	112.4 (2)	C26—C21—H21	106.8
C22—O6—C35	115.1 (2)	O6—C22—C21	104.8 (2)
C35—O7—C36	113.6 (3)	O6—C22—C23	108.7 (2)
O1—C8—O2	111.0 (3)	O6—C22—H22	109.7
O1—C8—O3	124.9 (4)	C21—C22—C23	114.0 (2)
O2—C8—O3	124.1 (4)	C21—C22—H22	109.7
O1—C9—C10	102.5 (2)	C23—C22—H22	109.8
O1—C9—C14	106.1 (2)	C22—C23—C24	110.9 (2)
O1—C9—C16	109.7 (3)	C22—C23—H23A	109.1
C10—C9—C14	114.6 (2)	C22—C23—H23B	109.0
C10—C9—C16	110.7 (2)	C24—C23—H23A	109.0
C14—C9—C16	112.5 (3)	C24—C23—H23B	109.0
O2—C10—C9	103.0 (2)	H23A—C23—H23B	109.7
O2—C10—C21	112.1 (2)	C23—C24—C25	108.1 (2)
O2—C10—H10	107.4	C23—C24—H24A	110.0
C9—C10—C21	118.7 (2)	C23—C24—H24B	109.7
C9—C10—H10	107.4	C25—C24—H24A	110.0
C21—C10—H10	107.5	C25—C24—H24B	109.8
O4—C11—C12	106.2 (2)	H24A—C24—H24B	109.3
O4—C11—C26	108.6 (2)	O5—C25—C24	110.9 (2)
O4—C11—H11	105.2	O5—C25—C26	108.9 (2)
C12—C11—C26	124.8 (2)	O5—C25—H25	108.1
C12—C11—H11	105.3	C24—C25—C26	113.1 (2)
C26—C11—H11	105.2	C24—C25—H25	107.9
C11—C12—C13	110.0 (2)	C26—C25—H25	107.9
C11—C12—C15	113.8 (2)	C11—C26—C21	112.0 (2)
C11—C12—C17	105.7 (2)	C11—C26—C25	104.7 (2)
C13—C12—C15	113.4 (3)	C11—C26—C27	112.1 (2)
C13—C12—C17	104.2 (3)	C21—C26—C25	107.5 (2)
C15—C12—C17	109.0 (2)	C21—C26—C27	111.4 (2)
C12—C13—C14	118.3 (3)	C25—C26—C27	108.6 (2)
C12—C13—H13A	107.1	C26—C27—H27A	109.4
C12—C13—H13B	107.2	C26—C27—H27B	109.5
C14—C13—H13A	107.2	C26—C27—H27C	109.4
C14—C13—H13B	107.3	H27A—C27—H27B	109.6
H13A—C13—H13B	109.6	H27A—C27—H27C	109.4
C9—C14—C13	112.1 (2)	H27B—C27—H27C	109.6
C9—C14—H14A	108.8	O5—C28—C29	109.9 (2)
C9—C14—H14B	108.8	O5—C28—H28A	109.4
C13—C14—H14A	108.8	O5—C28—H28B	109.3
C13—C14—H14B	108.9	C29—C28—H28A	109.4
H14A—C14—H14B	109.4	C29—C28—H28B	109.4
C12—C15—C16	118.9 (3)	H28A—C28—H28B	109.3
C12—C15—C18	120.2 (3)	C28—C29—C30	120.2 (3)
C16—C15—C18	120.8 (3)	C28—C29—C34	122.4 (3)
C9—C16—C15	106.2 (3)	C30—C29—C34	117.3 (3)
C9—C16—C19	110.7 (3)	C29—C30—C31	121.7 (3)
C9—C16—C20	110.7 (3)	C29—C30—H30	119.1
C15—C16—C19	108.0 (3)	C31—C30—H30	119.3
C15—C16—C20	113.6 (3)	C30—C31—C32	120.0 (4)
C19—C16—C20	107.6 (3)	C30—C31—H31	120.0
C12—C17—H17A	109.4	C32—C31—H31	119.9
C12—C17—H17B	109.5	C31—C32—C33	119.5 (4)
C12—C17—H17C	109.4	C31—C32—H32	120.3
H17A—C17—H17B	109.5	C33—C32—H32	120.2
H17A—C17—H17C	109.4	C32—C33—C34	120.4 (4)
H17B—C17—H17C	109.6	C32—C33—H33	119.8
C15—C18—H18A	119.9	C34—C33—H33	119.8
C15—C18—H18B	120.1	C29—C34—C33	121.1 (3)
H18A—C18—H18B	120.0	C29—C34—H34	119.4
C16—C19—H19A	109.4	C33—C34—H34	119.5
C16—C19—H19B	109.3	O6—C35—O7	114.1 (3)
C16—C19—H19C	109.5	O6—C35—H35A	108.2
H19A—C19—H19B	109.5	O6—C35—H35B	108.3
H19A—C19—H19C	109.6	O7—C35—H35A	108.4
H19B—C19—H19C	109.6	O7—C35—H35B	108.5
C16—C20—H20A	109.5	H35A—C35—H35B	109.3
C16—C20—H20B	109.8	O7—C36—H36A	109.4
C16—C20—H20C	109.6	O7—C36—H36B	109.5
H20A—C20—H20B	109.4	O7—C36—H36C	109.5
H20A—C20—H20C	109.2	H36A—C36—H36B	109.4
H20B—C20—H20C	109.4	H36A—C36—H36C	109.4
C10—C21—C22	110.2 (2)	H36B—C36—H36C	109.5
C10—C21—C26	109.9 (2)
O1—C8—O2—C10	−1.5 (4)	C11—C12—C13—C14	96.0 (3)
O1—C9—C10—O2	1.1 (3)	C11—C12—C15—C16	−115.4 (3)
O1—C9—C10—C21	125.7 (2)	C11—C12—C15—C18	66.1 (4)
O1—C9—C14—C13	169.3 (2)	C11—C26—C21—C22	157.4 (2)
O1—C9—C16—C15	173.4 (2)	C11—C26—C25—C24	−174.9 (2)
O1—C9—C16—C19	−69.6 (4)	C12—C11—C26—C21	36.3 (3)
O1—C9—C16—C20	49.6 (4)	C12—C11—C26—C25	152.5 (2)
O2—C8—O1—C9	2.3 (4)	C12—C11—C26—C27	−89.9 (3)
O2—C10—C9—C14	−113.4 (3)	C12—C15—C16—C19	−83.4 (3)
O2—C10—C9—C16	118.0 (3)	C12—C15—C16—C20	157.4 (3)
O2—C10—C21—C22	−11.5 (3)	C13—C12—C11—C26	−73.8 (3)
O2—C10—C21—C26	−140.7 (2)	C13—C12—C15—C16	11.4 (4)
O3—C8—O1—C9	−177.6 (3)	C13—C12—C15—C18	−167.1 (3)
O3—C8—O2—C10	178.4 (3)	C13—C14—C9—C16	49.3 (3)
O4—C11—C12—C13	158.9 (2)	C14—C9—C10—C21	11.2 (4)
O4—C11—C12—C15	−72.6 (3)	C14—C9—C16—C15	−68.7 (3)
O4—C11—C12—C17	47.0 (3)	C14—C9—C16—C19	48.3 (4)
O4—C11—C26—C21	162.6 (2)	C14—C9—C16—C20	167.5 (3)
O4—C11—C26—C25	−81.2 (2)	C14—C13—C12—C15	−32.7 (3)
O4—C11—C26—C27	36.4 (3)	C14—C13—C12—C17	−151.1 (3)
O5—C25—C24—C23	−171.0 (2)	C15—C12—C11—C26	54.7 (3)
O5—C25—C26—C11	61.4 (2)	C16—C9—C10—C21	−117.4 (3)
O5—C25—C26—C21	−179.3 (2)	C16—C15—C12—C17	126.9 (3)
O5—C25—C26—C27	−58.6 (3)	C17—C12—C11—C26	174.3 (2)
O5—C28—C29—C30	130.1 (3)	C17—C12—C15—C18	−51.6 (4)
O5—C28—C29—C34	−51.9 (4)	C18—C15—C16—C19	95.2 (4)
O6—C22—C21—C10	73.2 (2)	C18—C15—C16—C20	−24.1 (5)
O6—C22—C21—C26	−161.2 (2)	C21—C22—O6—C35	−147.2 (2)
O6—C22—C23—C24	166.8 (2)	C21—C22—C23—C24	50.3 (3)
O6—C35—O7—C36	−64.1 (4)	C21—C26—C25—C24	−55.6 (3)
O7—C35—O6—C22	−71.9 (3)	C22—C21—C26—C25	42.9 (3)
C8—O1—C9—C10	−2.0 (3)	C22—C21—C26—C27	−76.0 (3)
C8—O1—C9—C14	118.5 (3)	C22—C23—C24—C25	−61.2 (3)
C8—O1—C9—C16	−119.7 (3)	C23—C22—O6—C35	90.6 (3)
C8—O2—C10—C9	0.2 (3)	C23—C22—C21—C26	−42.4 (3)
C8—O2—C10—C21	−128.6 (3)	C23—C24—C25—C26	66.4 (3)
C9—C10—C21—C22	−131.6 (2)	C24—C25—O5—C28	82.2 (3)
C9—C10—C21—C26	99.3 (3)	C24—C25—C26—C27	65.1 (3)
C9—C14—C13—C12	2.8 (4)	C25—O5—C28—C29	−175.6 (2)
C9—C16—C15—C12	35.4 (4)	C26—C25—O5—C28	−152.8 (2)
C9—C16—C15—C18	−146.0 (3)	C28—C29—C30—C31	177.8 (4)
C10—C9—C14—C13	−78.3 (3)	C28—C29—C34—C33	−178.6 (3)
C10—C9—C16—C15	61.1 (3)	C29—C30—C31—C32	1.3 (6)
C10—C9—C16—C19	178.1 (3)	C29—C34—C33—C32	0.4 (5)
C10—C9—C16—C20	−62.7 (4)	C30—C29—C34—C33	−0.6 (5)
C10—C21—C22—C23	−168.1 (2)	C30—C31—C32—C33	−1.4 (6)
C10—C21—C26—C11	−76.8 (2)	C31—C30—C29—C34	−0.3 (5)
C10—C21—C26—C25	168.7 (2)	C31—C32—C33—C34	0.6 (6)
C10—C21—C26—C27	49.8 (3)	C31—C32—C33—C34	0.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5	0.82	2.04	2.711 (2)	139