Obacunone

Zhou, X.; Ji, C.; Fu, J.; Li, Y.-G.; Chen, T.

doi:10.1107/S1600536806046885

Obacunone

X. Zhou, C. Ji, J. Fu, Y.-G. Li and T. Chen

The title compound, C₂₆H₃₀O₇, crystallizes with three independent molecules in the asymmetric unit. The crystal structure is stabilized by intra- and intermolecular C—H

O hydrogen-bonding interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046885/rz2087sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046885/rz2087Isup2.hkl Contains datablock I

CCDC reference: 630222

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.045
wR factor = 0.112
Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O7     -   C26     ..      11.78 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         O7

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.29
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.52 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O7     -   C23     ..       5.67 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C62
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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           25.01
           From the CIF: _reflns_number_total               6625
           Count of symmetry unique reflns         6628
           Completeness (_total/calc)             99.95%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C30    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C35    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C39    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C40    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C41    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C43    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C56    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C57    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C58    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C61    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C65    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C66    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C67    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C69    = .          S

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

  27 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

Obacunone top

Crystal data top

C₂₆H₃₀O₇	F(000) = 2904
M_r = 454.50	D_x = 1.326 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2806 reflections
a = 12.531 (2) Å	θ = 2.1–26.1°
b = 23.041 (5) Å	µ = 0.10 mm⁻¹
c = 23.649 (5) Å	T = 293 K
V = 6828 (2) Å³	Block, colourless
Z = 12	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEX area-detector diffractometer	6625 independent reflections
Radiation source: fine-focus sealed tube	3328 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.972, T_max = 0.981	k = −27→26
34845 measured reflections	l = −28→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0501P)²] where P = (F_o² + 2F_c²)/3
S = 0.84	(Δ/σ)_max < 0.001
6625 reflections	Δρ_max = 0.20 e Å⁻³
909 parameters	Δρ_min = −0.21 e Å⁻³
3402 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00153 (17)

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
O1	0.0005 (3)	0.19056 (16)	0.96013 (14)	0.0771 (10)
O2	−0.0878 (3)	0.2288 (2)	0.88883 (17)	0.1064 (14)
O3	0.3613 (3)	0.01825 (17)	0.98026 (17)	0.0873 (12)
O4	0.6046 (3)	0.12341 (17)	0.99122 (15)	0.0886 (11)
O5	0.7003 (3)	0.05236 (19)	0.90189 (19)	0.0978 (12)
O6	0.6939 (4)	−0.0168 (2)	0.9663 (3)	0.160 (2)
O7	0.7697 (4)	0.1650 (3)	0.7502 (3)	0.159 (2)
O8	0.4192 (3)	0.31591 (15)	0.44019 (13)	0.0654 (9)
O9	0.2742 (4)	0.3495 (3)	0.40004 (19)	0.176 (3)
O10	0.6543 (2)	0.39193 (15)	0.65123 (13)	0.0671 (9)
O11	0.5451 (2)	0.26971 (14)	0.75424 (12)	0.0608 (8)
O12	0.5205 (2)	0.36795 (15)	0.83072 (12)	0.0672 (9)
O13	0.6954 (3)	0.36627 (16)	0.83349 (14)	0.0752 (10)
O14	0.1894 (3)	0.4059 (2)	0.88228 (17)	0.1028 (14)
O15	1.0580 (2)	0.32458 (13)	0.67204 (13)	0.0571 (8)
O16	1.0940 (3)	0.24572 (15)	0.72103 (16)	0.0814 (11)
O17	0.7828 (3)	0.54047 (14)	0.65897 (13)	0.0632 (9)
O18	0.8853 (2)	0.61457 (13)	0.79796 (12)	0.0565 (8)
O19	0.6579 (3)	0.63751 (13)	0.81367 (14)	0.0621 (9)
O20	0.6659 (3)	0.68626 (14)	0.73355 (14)	0.0714 (10)
O21	0.5427 (4)	0.55180 (18)	0.97283 (18)	0.0990 (13)
C1	−0.0031 (5)	0.2098 (2)	0.9062 (2)	0.0729 (15)
C2	0.0935 (5)	0.2128 (2)	0.8730 (2)	0.0715 (14)
H2	0.0853	0.2220	0.8350	0.086*
C3	0.1915 (4)	0.2039 (2)	0.8905 (2)	0.0657 (14)
H3	0.2445	0.2136	0.8647	0.079*
C4	0.2311 (4)	0.1804 (2)	0.94636 (19)	0.0619 (12)
C5	0.3469 (4)	0.1600 (2)	0.93362 (19)	0.0596 (12)
H5	0.3398	0.1357	0.8998	0.072*
C6	0.4041 (4)	0.1199 (2)	0.9777 (2)	0.0630 (13)
C7	0.3316 (5)	0.0675 (3)	0.9849 (2)	0.0748 (15)
C8	0.2168 (4)	0.0818 (2)	0.9994 (2)	0.0784 (15)
H8A	0.2142	0.0977	1.0373	0.094*
H8B	0.1754	0.0463	0.9992	0.094*
C9	0.1645 (4)	0.1257 (2)	0.9582 (2)	0.0617 (13)
H9	0.1612	0.1053	0.9219	0.074*
C10	0.0456 (4)	0.1339 (3)	0.9760 (2)	0.0720 (15)
C11	0.4277 (4)	0.2064 (2)	0.9166 (2)	0.0692 (14)
H11A	0.3914	0.2374	0.8966	0.083*
H11B	0.4599	0.2228	0.9503	0.083*
C12	0.5144 (4)	0.1809 (2)	0.8790 (2)	0.0712 (14)
H12A	0.5786	0.2041	0.8829	0.085*
H12B	0.4915	0.1832	0.8399	0.085*
C13	0.5414 (4)	0.1168 (2)	0.8932 (2)	0.0656 (13)
C14	0.5159 (4)	0.1055 (2)	0.9547 (2)	0.0655 (13)
C15	0.5847 (5)	0.0633 (3)	0.9837 (3)	0.0897 (17)
H15	0.5530	0.0427	1.0159	0.108*
C16	0.6643 (5)	0.0309 (3)	0.9503 (3)	0.1013 (19)
C17	0.6642 (4)	0.1102 (3)	0.8842 (2)	0.0799 (15)
H17	0.7004	0.1391	0.9078	0.096*
C18	0.2245 (5)	0.2295 (2)	0.9918 (2)	0.0814 (16)
H18A	0.1562	0.2481	0.9895	0.122*
H18B	0.2798	0.2575	0.9849	0.122*
H18C	0.2336	0.2130	1.0287	0.122*
C19	0.4154 (5)	0.1472 (3)	1.0374 (2)	0.0943 (18)
H19A	0.3460	0.1513	1.0542	0.141*
H19B	0.4483	0.1847	1.0342	0.141*
H19C	0.4587	0.1226	1.0607	0.141*
C20	−0.0228 (4)	0.0873 (3)	0.9470 (2)	0.0894 (18)
H20A	−0.0966	0.0935	0.9561	0.134*
H20B	−0.0012	0.0496	0.9598	0.134*
H20C	−0.0134	0.0898	0.9067	0.134*
C21	0.0251 (5)	0.1334 (3)	1.0391 (2)	0.099 (2)
H21A	0.0707	0.1612	1.0573	0.148*
H21B	0.0397	0.0954	1.0539	0.148*
H21C	−0.0481	0.1432	1.0463	0.148*
C22	0.4837 (4)	0.0731 (2)	0.8551 (2)	0.0780 (15)
H22A	0.5160	0.0355	0.8592	0.117*
H22B	0.4890	0.0854	0.8164	0.117*
H22C	0.4098	0.0709	0.8658	0.117*
C23	0.7465 (5)	0.1681 (4)	0.8054 (3)	0.122 (2)
H23	0.7596	0.2005	0.8277	0.147*
C24	0.7013 (4)	0.1179 (3)	0.8251 (3)	0.0934 (17)
C25	0.7005 (6)	0.0824 (4)	0.7772 (4)	0.130 (2)
H25	0.6739	0.0447	0.7776	0.156*
C26	0.7382 (5)	0.1052 (4)	0.7342 (3)	0.126 (2)
H26	0.7453	0.0881	0.6988	0.151*
C27	0.3194 (5)	0.3381 (3)	0.4438 (2)	0.0799 (16)
C28	0.2658 (4)	0.3408 (2)	0.4965 (2)	0.0644 (13)
H28	0.1966	0.3553	0.4961	0.077*
C29	0.3040 (4)	0.3248 (2)	0.5460 (2)	0.0604 (13)
H29	0.2555	0.3263	0.5757	0.073*
C30	0.4157 (3)	0.30432 (19)	0.56203 (17)	0.0431 (10)
C31	0.4236 (3)	0.31523 (18)	0.62623 (16)	0.0421 (10)
H31	0.4062	0.3565	0.6304	0.051*
C32	0.5348 (3)	0.30931 (19)	0.65448 (18)	0.0470 (11)
C33	0.6032 (3)	0.3545 (2)	0.62557 (19)	0.0519 (11)
C34	0.6060 (3)	0.3510 (2)	0.56217 (18)	0.0619 (13)
H34A	0.6468	0.3170	0.5514	0.074*
H34B	0.6435	0.3848	0.5478	0.074*
C35	0.4957 (3)	0.3477 (2)	0.53325 (17)	0.0504 (11)
H35	0.4641	0.3861	0.5397	0.060*
C36	0.5097 (3)	0.3442 (2)	0.46792 (18)	0.0521 (12)
C37	0.3438 (3)	0.28453 (19)	0.66513 (17)	0.0499 (11)
H37A	0.2775	0.2775	0.6451	0.060*
H37B	0.3725	0.2475	0.6773	0.060*
C38	0.3237 (3)	0.3232 (2)	0.71606 (18)	0.0528 (12)
H38A	0.2918	0.3000	0.7458	0.063*
H38B	0.2725	0.3529	0.7055	0.063*
C39	0.4249 (3)	0.35334 (19)	0.73993 (16)	0.0427 (10)
C40	0.5219 (3)	0.3196 (2)	0.71899 (17)	0.0461 (11)
C41	0.6156 (4)	0.3181 (2)	0.75609 (19)	0.0534 (12)
H41	0.6848	0.3130	0.7374	0.064*
C42	0.6160 (4)	0.3521 (2)	0.8096 (2)	0.0568 (12)
C43	0.4216 (3)	0.3474 (2)	0.80498 (18)	0.0601 (12)
H43	0.4120	0.3063	0.8146	0.072*
C44	0.4265 (4)	0.23985 (19)	0.54478 (19)	0.0621 (13)
H44A	0.5006	0.2294	0.5437	0.093*
H44B	0.3954	0.2342	0.5081	0.093*
H44C	0.3901	0.2160	0.5719	0.093*
C45	0.5888 (4)	0.2496 (2)	0.6462 (2)	0.0690 (14)
H45A	0.6134	0.2462	0.6079	0.104*
H45B	0.5383	0.2193	0.6540	0.104*
H45C	0.6483	0.2462	0.6715	0.104*
C46	0.5184 (4)	0.4047 (2)	0.44315 (19)	0.0679 (14)
H46A	0.5299	0.4021	0.4031	0.102*
H46B	0.5773	0.4247	0.4603	0.102*
H46C	0.4536	0.4257	0.4503	0.102*
C47	0.6014 (4)	0.3068 (2)	0.4475 (2)	0.0720 (15)
H47A	0.5968	0.2691	0.4646	0.108*
H47B	0.6679	0.3246	0.4577	0.108*
H47C	0.5977	0.3029	0.4071	0.108*
C48	0.4320 (3)	0.41737 (19)	0.72268 (18)	0.0547 (12)
H48A	0.4918	0.4351	0.7412	0.082*
H48B	0.3676	0.4370	0.7336	0.082*
H48C	0.4409	0.4201	0.6825	0.082*
C49	0.2446 (4)	0.3627 (3)	0.8563 (2)	0.0817 (16)
H49	0.2214	0.3244	0.8539	0.098*
C50	0.3366 (4)	0.3824 (3)	0.8347 (2)	0.0649 (13)
C51	0.3383 (5)	0.4419 (3)	0.8501 (2)	0.0889 (17)
H51	0.3923	0.4684	0.8423	0.107*
C52	0.2492 (5)	0.4526 (3)	0.8775 (3)	0.099 (2)
H52	0.2305	0.4888	0.8917	0.119*
C53	1.0377 (4)	0.2884 (2)	0.7158 (2)	0.0599 (13)
C54	0.9604 (3)	0.3050 (2)	0.7579 (2)	0.0580 (12)
H54	0.9267	0.2750	0.7773	0.070*
C55	0.9324 (3)	0.3587 (2)	0.7719 (2)	0.0541 (12)
H55	0.8885	0.3628	0.8034	0.065*
C56	0.9650 (3)	0.41435 (18)	0.74172 (16)	0.0422 (10)
C57	0.8975 (3)	0.46329 (17)	0.76889 (16)	0.0419 (10)
H57	0.8238	0.4497	0.7649	0.050*
C58	0.8977 (3)	0.52331 (19)	0.73865 (18)	0.0470 (11)
C59	0.8537 (4)	0.5126 (2)	0.67990 (18)	0.0485 (11)
C60	0.9098 (4)	0.4645 (2)	0.64788 (18)	0.0573 (12)
H60A	0.9801	0.4781	0.6370	0.069*
H60B	0.8703	0.4568	0.6134	0.069*
C61	0.9224 (3)	0.40707 (18)	0.68051 (16)	0.0473 (11)
H61	0.8492	0.3930	0.6854	0.057*
C62	0.9773 (4)	0.3598 (2)	0.6432 (2)	0.0663 (14)
C63	0.9098 (3)	0.47394 (19)	0.83268 (17)	0.0512 (11)
H63A	0.9680	0.5008	0.8395	0.061*
H63B	0.9260	0.4377	0.8517	0.061*
C64	0.8051 (3)	0.49936 (18)	0.85607 (17)	0.0487 (11)
H64A	0.8206	0.5198	0.8910	0.058*
H64B	0.7572	0.4676	0.8651	0.058*
C65	0.7467 (3)	0.54172 (19)	0.81513 (17)	0.0451 (11)
C66	0.8290 (3)	0.56534 (18)	0.77308 (17)	0.0428 (10)
C67	0.8109 (4)	0.62455 (19)	0.7527 (2)	0.0546 (12)
H67	0.8421	0.6340	0.7158	0.066*
C68	0.7079 (4)	0.6526 (2)	0.7658 (2)	0.0562 (12)
C69	0.7048 (4)	0.59314 (19)	0.85058 (19)	0.0530 (11)
H69	0.7649	0.6104	0.8710	0.064*
C70	1.0864 (3)	0.4243 (2)	0.74710 (18)	0.0555 (12)
H70A	1.1002	0.4504	0.7778	0.083*
H70B	1.1132	0.4406	0.7126	0.083*
H70C	1.1212	0.3879	0.7542	0.083*
C71	1.0095 (3)	0.5512 (2)	0.7308 (2)	0.0661 (14)
H71A	1.0502	0.5287	0.7044	0.099*
H71B	1.0459	0.5523	0.7665	0.099*
H71C	1.0014	0.5900	0.7166	0.099*
C72	0.8912 (4)	0.3167 (3)	0.6220 (2)	0.106 (2)
H72A	0.9240	0.2877	0.5987	0.158*
H72B	0.8386	0.3373	0.6004	0.158*
H72C	0.8575	0.2985	0.6538	0.158*
C73	1.0421 (5)	0.3831 (3)	0.5953 (2)	0.117 (2)
H73A	1.0943	0.4098	0.6097	0.176*
H73B	0.9961	0.4028	0.5691	0.176*
H73C	1.0775	0.3517	0.5764	0.176*
C74	0.6530 (3)	0.51264 (19)	0.78365 (18)	0.0497 (12)
H74A	0.6107	0.5419	0.7653	0.075*
H74B	0.6095	0.4918	0.8102	0.075*
H74C	0.6804	0.4862	0.7558	0.075*
C75	0.6365 (5)	0.5636 (2)	0.9463 (2)	0.0790 (15)
H75	0.7033	0.5615	0.9634	0.095*
C76	0.6196 (4)	0.5787 (2)	0.8920 (2)	0.0615 (13)
C77	0.5086 (5)	0.5787 (2)	0.8843 (2)	0.0813 (16)
H77	0.4722	0.5885	0.8514	0.098*
C78	0.4639 (5)	0.5616 (3)	0.9342 (3)	0.0936 (18)
H78	0.3911	0.5572	0.9408	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.100 (3)	0.076 (3)	0.055 (2)	0.023 (2)	0.011 (2)	−0.0080 (19)
O2	0.092 (3)	0.132 (4)	0.095 (3)	0.037 (3)	0.000 (3)	0.011 (3)
O3	0.089 (3)	0.057 (3)	0.116 (3)	0.001 (2)	−0.004 (2)	0.022 (2)
O4	0.095 (2)	0.092 (3)	0.079 (2)	−0.017 (2)	−0.042 (2)	0.025 (2)
O5	0.075 (2)	0.092 (3)	0.126 (3)	0.004 (2)	−0.015 (2)	0.031 (3)
O6	0.124 (4)	0.114 (4)	0.243 (6)	0.031 (3)	0.018 (4)	0.084 (4)
O7	0.109 (3)	0.222 (5)	0.148 (4)	0.025 (4)	0.010 (3)	0.063 (5)
O8	0.062 (2)	0.079 (2)	0.0552 (19)	−0.0176 (19)	0.0025 (17)	−0.0162 (18)
O9	0.091 (3)	0.367 (8)	0.071 (3)	0.005 (4)	−0.010 (3)	0.036 (4)
O10	0.060 (2)	0.082 (3)	0.058 (2)	−0.0236 (19)	−0.0018 (18)	−0.0019 (19)
O11	0.0573 (19)	0.058 (2)	0.067 (2)	0.0022 (16)	−0.0087 (16)	0.0162 (17)
O12	0.0510 (19)	0.105 (3)	0.0461 (18)	0.0046 (19)	−0.0066 (16)	0.0026 (18)
O13	0.0494 (19)	0.103 (3)	0.073 (2)	−0.002 (2)	−0.0116 (19)	−0.003 (2)
O14	0.078 (3)	0.155 (4)	0.075 (3)	0.024 (3)	0.027 (2)	0.012 (3)
O15	0.0478 (18)	0.062 (2)	0.061 (2)	0.0190 (16)	−0.0004 (16)	−0.0035 (17)
O16	0.077 (2)	0.054 (2)	0.113 (3)	0.024 (2)	0.016 (2)	0.004 (2)
O17	0.069 (2)	0.062 (2)	0.059 (2)	0.0175 (19)	−0.0102 (18)	0.0066 (17)
O18	0.0636 (18)	0.0418 (18)	0.064 (2)	−0.0074 (16)	−0.0082 (17)	−0.0061 (15)
O19	0.081 (2)	0.0405 (19)	0.065 (2)	0.0153 (17)	0.0073 (19)	−0.0030 (16)
O20	0.099 (3)	0.052 (2)	0.063 (2)	0.022 (2)	−0.011 (2)	0.0011 (18)
O21	0.110 (3)	0.095 (3)	0.093 (3)	0.004 (3)	0.034 (3)	−0.005 (2)
C1	0.090 (4)	0.061 (3)	0.067 (3)	0.016 (3)	−0.001 (3)	−0.012 (3)
C2	0.089 (4)	0.071 (3)	0.055 (3)	0.022 (3)	0.001 (3)	0.001 (3)
C3	0.080 (3)	0.061 (3)	0.056 (3)	0.011 (3)	0.002 (3)	0.009 (2)
C4	0.086 (3)	0.050 (3)	0.049 (3)	0.001 (3)	−0.002 (3)	0.001 (2)
C5	0.081 (3)	0.049 (3)	0.048 (3)	−0.002 (3)	−0.010 (2)	0.007 (2)
C6	0.079 (3)	0.057 (3)	0.053 (3)	−0.003 (3)	−0.012 (2)	0.010 (2)
C7	0.090 (4)	0.063 (3)	0.071 (3)	0.004 (3)	−0.008 (3)	0.021 (3)
C8	0.088 (3)	0.068 (3)	0.080 (3)	0.003 (3)	0.005 (3)	0.017 (3)
C9	0.081 (3)	0.056 (3)	0.048 (3)	0.004 (3)	0.001 (3)	−0.002 (2)
C10	0.090 (3)	0.078 (4)	0.048 (3)	0.011 (3)	0.008 (3)	0.004 (3)
C11	0.083 (3)	0.056 (3)	0.068 (3)	−0.005 (3)	−0.020 (3)	0.008 (2)
C12	0.075 (3)	0.068 (3)	0.071 (3)	−0.007 (3)	−0.014 (3)	0.018 (3)
C13	0.071 (3)	0.059 (3)	0.067 (3)	−0.003 (3)	−0.021 (3)	0.008 (2)
C14	0.073 (3)	0.057 (3)	0.067 (3)	−0.014 (3)	−0.028 (3)	0.019 (2)
C15	0.080 (3)	0.085 (4)	0.105 (4)	0.004 (3)	−0.018 (3)	0.044 (3)
C16	0.086 (4)	0.087 (4)	0.130 (5)	0.011 (4)	−0.019 (4)	0.041 (4)
C17	0.067 (3)	0.083 (3)	0.090 (3)	−0.004 (3)	−0.017 (3)	0.026 (3)
C18	0.111 (4)	0.066 (4)	0.067 (3)	0.004 (3)	−0.005 (3)	−0.017 (3)
C19	0.131 (5)	0.094 (4)	0.057 (3)	0.002 (4)	−0.029 (3)	0.003 (3)
C20	0.090 (4)	0.084 (4)	0.093 (4)	0.000 (4)	0.004 (4)	−0.009 (4)
C21	0.124 (5)	0.119 (5)	0.053 (3)	0.015 (4)	0.025 (3)	0.011 (3)
C22	0.065 (3)	0.082 (4)	0.087 (4)	−0.006 (3)	−0.012 (3)	−0.020 (3)
C23	0.107 (4)	0.147 (5)	0.113 (4)	0.004 (4)	0.003 (4)	0.031 (4)
C24	0.058 (3)	0.122 (5)	0.100 (4)	−0.011 (3)	−0.013 (3)	0.011 (4)
C25	0.095 (4)	0.164 (6)	0.132 (5)	−0.032 (4)	0.003 (4)	0.000 (5)
C26	0.077 (4)	0.204 (7)	0.098 (5)	−0.021 (5)	0.000 (4)	−0.008 (5)
C27	0.070 (3)	0.116 (4)	0.054 (3)	−0.015 (3)	−0.012 (3)	0.004 (3)
C28	0.051 (3)	0.090 (4)	0.053 (3)	0.005 (3)	0.000 (3)	0.003 (3)
C29	0.049 (3)	0.080 (3)	0.053 (3)	−0.003 (3)	0.003 (2)	−0.003 (3)
C30	0.039 (2)	0.049 (3)	0.042 (2)	−0.008 (2)	0.001 (2)	−0.002 (2)
C31	0.040 (2)	0.041 (2)	0.045 (2)	0.001 (2)	0.003 (2)	0.002 (2)
C32	0.038 (2)	0.050 (3)	0.053 (3)	−0.006 (2)	0.000 (2)	0.002 (2)
C33	0.039 (2)	0.067 (3)	0.050 (3)	−0.003 (2)	0.000 (2)	0.000 (2)
C34	0.048 (3)	0.083 (3)	0.055 (3)	−0.016 (3)	0.005 (2)	0.002 (3)
C35	0.050 (2)	0.054 (3)	0.047 (2)	−0.010 (2)	0.004 (2)	−0.002 (2)
C36	0.050 (3)	0.063 (3)	0.043 (2)	−0.009 (2)	0.002 (2)	−0.007 (2)
C37	0.049 (2)	0.054 (3)	0.047 (3)	−0.011 (2)	0.002 (2)	0.001 (2)
C38	0.041 (2)	0.065 (3)	0.052 (3)	−0.004 (2)	0.002 (2)	0.005 (2)
C39	0.034 (2)	0.053 (3)	0.042 (2)	0.002 (2)	0.0011 (19)	0.007 (2)
C40	0.039 (2)	0.055 (3)	0.044 (2)	−0.002 (2)	−0.004 (2)	0.013 (2)
C41	0.045 (2)	0.061 (3)	0.054 (3)	−0.001 (2)	0.000 (2)	0.001 (2)
C42	0.050 (3)	0.072 (3)	0.049 (3)	0.001 (3)	−0.002 (3)	0.016 (2)
C43	0.044 (2)	0.090 (3)	0.046 (3)	−0.007 (2)	−0.003 (2)	0.011 (2)
C44	0.073 (3)	0.050 (3)	0.063 (3)	−0.007 (3)	0.003 (3)	−0.007 (2)
C45	0.064 (3)	0.065 (3)	0.078 (3)	0.024 (3)	−0.009 (3)	−0.007 (3)
C46	0.078 (3)	0.073 (4)	0.053 (3)	−0.014 (3)	0.002 (3)	0.007 (3)
C47	0.065 (3)	0.087 (4)	0.064 (3)	0.008 (3)	0.024 (3)	−0.020 (3)
C48	0.060 (3)	0.052 (3)	0.052 (3)	−0.005 (2)	−0.001 (2)	−0.002 (2)
C49	0.071 (3)	0.102 (4)	0.073 (3)	0.008 (3)	0.012 (3)	0.019 (3)
C50	0.046 (3)	0.103 (4)	0.045 (3)	0.000 (3)	0.003 (2)	0.008 (3)
C51	0.075 (3)	0.119 (4)	0.072 (3)	−0.009 (3)	0.015 (3)	−0.025 (3)
C52	0.091 (4)	0.135 (5)	0.070 (4)	0.014 (4)	0.007 (4)	−0.033 (4)
C53	0.052 (3)	0.052 (3)	0.075 (3)	0.003 (3)	0.000 (3)	−0.009 (3)
C54	0.055 (3)	0.050 (3)	0.070 (3)	0.008 (2)	0.007 (3)	−0.001 (2)
C55	0.049 (2)	0.053 (3)	0.060 (3)	0.011 (2)	0.008 (2)	0.000 (2)
C56	0.045 (2)	0.045 (2)	0.037 (2)	0.008 (2)	0.001 (2)	0.000 (2)
C57	0.042 (2)	0.047 (2)	0.037 (2)	0.003 (2)	−0.0050 (19)	−0.0012 (19)
C58	0.049 (2)	0.047 (3)	0.046 (2)	0.002 (2)	−0.005 (2)	0.000 (2)
C59	0.053 (3)	0.047 (3)	0.045 (3)	0.003 (2)	−0.002 (2)	0.005 (2)
C60	0.062 (3)	0.065 (3)	0.045 (3)	0.015 (3)	0.001 (2)	0.003 (2)
C61	0.048 (2)	0.049 (3)	0.046 (2)	0.011 (2)	−0.002 (2)	−0.005 (2)
C62	0.063 (3)	0.082 (3)	0.054 (3)	0.033 (3)	−0.004 (3)	−0.017 (3)
C63	0.061 (3)	0.053 (3)	0.040 (2)	0.003 (2)	−0.004 (2)	0.002 (2)
C64	0.067 (3)	0.041 (3)	0.039 (2)	0.008 (2)	−0.001 (2)	−0.007 (2)
C65	0.053 (2)	0.039 (2)	0.043 (2)	0.005 (2)	−0.003 (2)	−0.004 (2)
C66	0.050 (2)	0.036 (2)	0.042 (2)	−0.004 (2)	−0.010 (2)	−0.002 (2)
C67	0.068 (3)	0.040 (3)	0.055 (3)	−0.001 (2)	0.001 (2)	0.001 (2)
C68	0.079 (3)	0.040 (3)	0.050 (3)	0.006 (3)	−0.008 (3)	−0.012 (2)
C69	0.069 (3)	0.038 (3)	0.051 (3)	0.006 (2)	−0.003 (2)	−0.011 (2)
C70	0.040 (3)	0.066 (3)	0.060 (3)	0.010 (2)	−0.003 (2)	−0.002 (2)
C71	0.054 (3)	0.059 (3)	0.086 (4)	−0.006 (3)	0.008 (3)	0.000 (3)
C72	0.088 (4)	0.112 (5)	0.117 (5)	0.043 (4)	−0.043 (4)	−0.070 (4)
C73	0.139 (5)	0.149 (6)	0.063 (4)	0.092 (5)	0.040 (4)	0.029 (4)
C74	0.048 (3)	0.047 (3)	0.054 (3)	0.005 (2)	0.001 (2)	−0.011 (2)
C75	0.083 (4)	0.080 (4)	0.074 (4)	0.004 (3)	0.026 (3)	−0.009 (3)
C76	0.075 (3)	0.053 (3)	0.056 (3)	0.005 (3)	0.011 (3)	−0.009 (2)
C77	0.082 (4)	0.080 (4)	0.082 (4)	0.013 (3)	0.013 (3)	−0.012 (3)
C78	0.083 (4)	0.095 (4)	0.103 (4)	0.005 (4)	0.033 (4)	−0.028 (4)

Geometric parameters (Å, º) top

O1—C1	1.352 (6)	C32—C45	1.546 (6)
O1—C10	1.471 (6)	C32—C40	1.552 (6)
O2—C1	1.219 (6)	C33—C34	1.502 (6)
O3—C7	1.198 (6)	C34—C35	1.544 (6)
O4—C15	1.420 (7)	C34—H34A	0.9700
O4—C14	1.466 (5)	C34—H34B	0.9700
O5—C16	1.325 (7)	C35—C36	1.557 (6)
O5—C17	1.468 (6)	C35—H35	0.9800
O6—C16	1.222 (7)	C36—C47	1.515 (6)
O7—C23	1.339 (8)	C36—C46	1.517 (6)
O7—C26	1.482 (9)	C37—C38	1.520 (6)
O8—C27	1.353 (6)	C37—H37A	0.9700
O8—C36	1.463 (5)	C37—H37B	0.9700
O9—C27	1.210 (6)	C38—C39	1.551 (5)
O10—C33	1.233 (5)	C38—H38A	0.9700
O11—C41	1.423 (5)	C38—H38B	0.9700
O11—C40	1.449 (5)	C39—C40	1.526 (5)
O12—C42	1.347 (5)	C39—C48	1.533 (6)
O12—C43	1.460 (5)	C39—C43	1.545 (5)
O13—C42	1.190 (5)	C40—C41	1.466 (6)
O14—C52	1.317 (7)	C41—C42	1.488 (6)
O14—C49	1.358 (6)	C41—H41	0.9800
O15—C53	1.353 (6)	C43—C50	1.510 (7)
O15—C62	1.465 (5)	C43—H43	0.9800
O16—C53	1.216 (5)	C44—H44A	0.9600
O17—C59	1.203 (5)	C44—H44B	0.9600
O18—C67	1.438 (5)	C44—H44C	0.9600
O18—C66	1.460 (5)	C45—H45A	0.9600
O19—C68	1.339 (5)	C45—H45B	0.9600
O19—C69	1.467 (5)	C45—H45C	0.9600
O20—C68	1.209 (5)	C46—H46A	0.9600
O21—C75	1.360 (6)	C46—H46B	0.9600
O21—C78	1.364 (7)	C46—H46C	0.9600
C1—C2	1.444 (7)	C47—H47A	0.9600
C2—C3	1.312 (6)	C47—H47B	0.9600
C2—H2	0.9300	C47—H47C	0.9600
C3—C4	1.512 (6)	C48—H48A	0.9600
C3—H3	0.9300	C48—H48B	0.9600
C4—C9	1.538 (6)	C48—H48C	0.9600
C4—C5	1.554 (7)	C49—C50	1.340 (6)
C4—C18	1.562 (6)	C49—H49	0.9300
C5—C11	1.527 (6)	C50—C51	1.420 (7)
C5—C6	1.566 (6)	C51—C52	1.314 (7)
C5—H5	0.9800	C51—H51	0.9300
C6—C7	1.521 (7)	C52—H52	0.9300
C6—C14	1.539 (7)	C53—C54	1.441 (6)
C6—C19	1.554 (7)	C54—C55	1.329 (6)
C7—C8	1.516 (7)	C54—H54	0.9300
C8—C9	1.548 (6)	C55—C56	1.523 (6)
C8—H8A	0.9700	C55—H55	0.9300
C8—H8B	0.9700	C56—C70	1.543 (6)
C9—C10	1.560 (7)	C56—C57	1.549 (5)
C9—H9	0.9800	C56—C61	1.552 (5)
C10—C21	1.514 (6)	C57—C63	1.536 (5)
C10—C20	1.537 (7)	C57—C58	1.557 (6)
C11—C12	1.523 (6)	C57—H57	0.9800
C11—H11A	0.9700	C58—C59	1.515 (6)
C11—H11B	0.9700	C58—C66	1.531 (6)
C12—C13	1.551 (7)	C58—C71	1.552 (6)
C12—H12A	0.9700	C59—C60	1.515 (6)
C12—H12B	0.9700	C60—C61	1.539 (6)
C13—C14	1.510 (7)	C60—H60A	0.9700
C13—C22	1.534 (6)	C60—H60B	0.9700
C13—C17	1.562 (7)	C61—C62	1.562 (6)
C14—C15	1.471 (7)	C61—H61	0.9800
C15—C16	1.475 (9)	C62—C73	1.493 (7)
C15—H15	0.9800	C62—C72	1.549 (7)
C17—C24	1.482 (8)	C63—C64	1.539 (6)
C17—H17	0.9800	C63—H63A	0.9700
C18—H18A	0.9600	C63—H63B	0.9700
C18—H18B	0.9600	C64—C65	1.557 (6)
C18—H18C	0.9600	C64—H64A	0.9700
C19—H19A	0.9600	C64—H64B	0.9700
C19—H19B	0.9600	C65—C66	1.532 (6)
C19—H19C	0.9600	C65—C69	1.544 (5)
C20—H20A	0.9600	C65—C74	1.544 (6)
C20—H20B	0.9600	C66—C67	1.465 (6)
C20—H20C	0.9600	C67—C68	1.476 (6)
C21—H21A	0.9600	C67—H67	0.9800
C21—H21B	0.9600	C69—C76	1.486 (6)
C21—H21C	0.9600	C69—H69	0.9800
C22—H22A	0.9600	C70—H70A	0.9600
C22—H22B	0.9600	C70—H70B	0.9600
C22—H22C	0.9600	C70—H70C	0.9600
C23—C24	1.369 (9)	C71—H71A	0.9600
C23—H23	0.9300	C71—H71B	0.9600
C24—C25	1.398 (9)	C71—H71C	0.9600
C25—C26	1.237 (9)	C72—H72A	0.9600
C25—H25	0.9300	C72—H72B	0.9600
C26—H26	0.9300	C72—H72C	0.9600
C27—C28	1.418 (7)	C73—H73A	0.9600
C28—C29	1.316 (6)	C73—H73B	0.9600
C28—H28	0.9300	C73—H73C	0.9600
C29—C30	1.525 (6)	C74—H74A	0.9600
C29—H29	0.9300	C74—H74B	0.9600
C30—C31	1.542 (5)	C74—H74C	0.9600
C30—C44	1.546 (6)	C75—C76	1.347 (7)
C30—C35	1.571 (6)	C75—H75	0.9300
C31—C37	1.532 (5)	C76—C77	1.404 (7)
C31—C32	1.551 (5)	C77—C78	1.363 (7)
C31—H31	0.9800	C77—H77	0.9300
C32—C33	1.513 (6)	C78—H78	0.9300

C1—O1—C10	123.0 (4)	H38A—C38—H38B	107.6
C15—O4—C14	61.2 (3)	C40—C39—C48	111.0 (3)
C16—O5—C17	118.7 (5)	C40—C39—C43	107.4 (3)
C23—O7—C26	103.9 (7)	C48—C39—C43	110.6 (4)
C27—O8—C36	121.3 (4)	C40—C39—C38	107.7 (3)
C41—O11—C40	61.4 (3)	C48—C39—C38	112.4 (3)
C42—O12—C43	120.7 (4)	C43—C39—C38	107.5 (3)
C52—O14—C49	105.7 (5)	O11—C40—C41	58.4 (3)
C53—O15—C62	124.6 (4)	O11—C40—C39	112.2 (3)
C67—O18—C66	60.7 (3)	C41—C40—C39	117.1 (4)
C68—O19—C69	119.8 (4)	O11—C40—C32	115.1 (4)
C75—O21—C78	106.5 (5)	C41—C40—C32	120.1 (4)
O2—C1—O1	117.7 (5)	C39—C40—C32	118.7 (3)
O2—C1—C2	122.0 (5)	O11—C41—C40	60.2 (3)
O1—C1—C2	120.0 (5)	O11—C41—C42	116.2 (4)
C3—C2—C1	127.3 (5)	C40—C41—C42	120.0 (4)
C3—C2—H2	116.3	O11—C41—H41	116.2
C1—C2—H2	116.3	C40—C41—H41	116.2
C2—C3—C4	129.7 (5)	C42—C41—H41	116.2
C2—C3—H3	115.2	O13—C42—O12	119.4 (5)
C4—C3—H3	115.2	O13—C42—C41	123.5 (5)
C3—C4—C9	106.0 (4)	O12—C42—C41	117.1 (4)
C3—C4—C5	104.2 (4)	O12—C43—C50	103.4 (4)
C9—C4—C5	107.1 (4)	O12—C43—C39	111.3 (3)
C3—C4—C18	108.8 (4)	C50—C43—C39	115.8 (4)
C9—C4—C18	116.1 (4)	O12—C43—H43	108.7
C5—C4—C18	113.7 (4)	C50—C43—H43	108.7
C11—C5—C4	117.3 (4)	C39—C43—H43	108.7
C11—C5—C6	106.5 (4)	C30—C44—H44A	109.5
C4—C5—C6	118.5 (4)	C30—C44—H44B	109.5
C11—C5—H5	104.3	H44A—C44—H44B	109.5
C4—C5—H5	104.3	C30—C44—H44C	109.5
C6—C5—H5	104.3	H44A—C44—H44C	109.5
C7—C6—C14	114.4 (4)	H44B—C44—H44C	109.5
C7—C6—C19	105.9 (4)	C32—C45—H45A	109.5
C14—C6—C19	109.0 (4)	C32—C45—H45B	109.5
C7—C6—C5	105.7 (4)	H45A—C45—H45B	109.5
C14—C6—C5	108.0 (4)	C32—C45—H45C	109.5
C19—C6—C5	114.0 (4)	H45A—C45—H45C	109.5
O3—C7—C8	121.5 (5)	H45B—C45—H45C	109.5
O3—C7—C6	123.8 (5)	C36—C46—H46A	109.5
C8—C7—C6	114.7 (5)	C36—C46—H46B	109.5
C7—C8—C9	113.7 (4)	H46A—C46—H46B	109.5
C7—C8—H8A	108.8	C36—C46—H46C	109.5
C9—C8—H8A	108.8	H46A—C46—H46C	109.5
C7—C8—H8B	108.8	H46B—C46—H46C	109.5
C9—C8—H8B	108.8	C36—C47—H47A	109.5
H8A—C8—H8B	107.7	C36—C47—H47B	109.5
C4—C9—C8	114.8 (4)	H47A—C47—H47B	109.5
C4—C9—C10	117.9 (4)	C36—C47—H47C	109.5
C8—C9—C10	108.3 (4)	H47A—C47—H47C	109.5
C4—C9—H9	104.8	H47B—C47—H47C	109.5
C8—C9—H9	104.8	C39—C48—H48A	109.5
C10—C9—H9	104.8	C39—C48—H48B	109.5
O1—C10—C21	101.2 (4)	H48A—C48—H48B	109.5
O1—C10—C20	106.9 (4)	C39—C48—H48C	109.5
C21—C10—C20	109.9 (5)	H48A—C48—H48C	109.5
O1—C10—C9	114.0 (4)	H48B—C48—H48C	109.5
C21—C10—C9	115.3 (5)	C50—C49—O14	111.2 (6)
C20—C10—C9	109.1 (4)	C50—C49—H49	124.4
C12—C11—C5	110.9 (4)	O14—C49—H49	124.4
C12—C11—H11A	109.5	C49—C50—C51	104.0 (5)
C5—C11—H11A	109.5	C49—C50—C43	127.1 (6)
C12—C11—H11B	109.5	C51—C50—C43	128.7 (5)
C5—C11—H11B	109.5	C52—C51—C50	107.1 (6)
H11A—C11—H11B	108.1	C52—C51—H51	126.4
C11—C12—C13	113.4 (4)	C50—C51—H51	126.4
C11—C12—H12A	108.9	C51—C52—O14	111.9 (7)
C13—C12—H12A	108.9	C51—C52—H52	124.1
C11—C12—H12B	108.9	O14—C52—H52	124.1
C13—C12—H12B	108.9	O16—C53—O15	117.9 (5)
H12A—C12—H12B	107.7	O16—C53—C54	122.3 (5)
C14—C13—C22	110.7 (4)	O15—C53—C54	119.4 (5)
C14—C13—C12	109.1 (4)	C55—C54—C53	126.7 (5)
C22—C13—C12	113.3 (4)	C55—C54—H54	116.7
C14—C13—C17	108.9 (4)	C53—C54—H54	116.7
C22—C13—C17	108.6 (5)	C54—C55—C56	126.6 (4)
C12—C13—C17	106.1 (4)	C54—C55—H55	116.7
O4—C14—C15	57.8 (3)	C56—C55—H55	116.7
O4—C14—C13	111.0 (4)	C55—C56—C70	110.5 (3)
C15—C14—C13	116.1 (5)	C55—C56—C57	105.8 (3)
O4—C14—C6	114.9 (4)	C70—C56—C57	113.4 (4)
C15—C14—C6	120.7 (5)	C55—C56—C61	104.7 (3)
C13—C14—C6	119.7 (4)	C70—C56—C61	115.6 (3)
O4—C15—C14	61.0 (3)	C57—C56—C61	106.1 (3)
O4—C15—C16	116.1 (5)	C63—C57—C56	118.0 (3)
C14—C15—C16	118.7 (6)	C63—C57—C58	108.0 (3)
O4—C15—H15	116.5	C56—C57—C58	117.1 (3)
C14—C15—H15	116.5	C63—C57—H57	104.0
C16—C15—H15	116.5	C56—C57—H57	104.0
O6—C16—O5	120.0 (8)	C58—C57—H57	104.0
O6—C16—C15	119.6 (7)	C59—C58—C66	112.7 (3)
O5—C16—C15	120.3 (6)	C59—C58—C71	106.6 (4)
O5—C17—C24	106.3 (5)	C66—C58—C71	108.0 (4)
O5—C17—C13	110.6 (4)	C59—C58—C57	106.0 (3)
C24—C17—C13	115.3 (4)	C66—C58—C57	108.5 (3)
O5—C17—H17	108.1	C71—C58—C57	115.2 (4)
C24—C17—H17	108.1	O17—C59—C60	121.9 (4)
C13—C17—H17	108.1	O17—C59—C58	124.0 (4)
C4—C18—H18A	109.5	C60—C59—C58	114.1 (4)
C4—C18—H18B	109.5	C59—C60—C61	115.2 (4)
H18A—C18—H18B	109.5	C59—C60—H60A	108.5
C4—C18—H18C	109.5	C61—C60—H60A	108.5
H18A—C18—H18C	109.5	C59—C60—H60B	108.5
H18B—C18—H18C	109.5	C61—C60—H60B	108.5
C6—C19—H19A	109.5	H60A—C60—H60B	107.5
C6—C19—H19B	109.5	C60—C61—C56	114.2 (3)
H19A—C19—H19B	109.5	C60—C61—C62	111.2 (3)
C6—C19—H19C	109.5	C56—C61—C62	116.8 (3)
H19A—C19—H19C	109.5	C60—C61—H61	104.3
H19B—C19—H19C	109.5	C56—C61—H61	104.3
C10—C20—H20A	109.5	C62—C61—H61	104.3
C10—C20—H20B	109.5	O15—C62—C73	100.2 (4)
H20A—C20—H20B	109.5	O15—C62—C72	106.1 (4)
C10—C20—H20C	109.5	C73—C62—C72	111.4 (5)
H20A—C20—H20C	109.5	O15—C62—C61	115.3 (4)
H20B—C20—H20C	109.5	C73—C62—C61	114.6 (5)
C10—C21—H21A	109.5	C72—C62—C61	108.8 (4)
C10—C21—H21B	109.5	C57—C63—C64	109.2 (3)
H21A—C21—H21B	109.5	C57—C63—H63A	109.8
C10—C21—H21C	109.5	C64—C63—H63A	109.8
H21A—C21—H21C	109.5	C57—C63—H63B	109.8
H21B—C21—H21C	109.5	C64—C63—H63B	109.8
C13—C22—H22A	109.5	H63A—C63—H63B	108.3
C13—C22—H22B	109.5	C63—C64—C65	114.5 (4)
H22A—C22—H22B	109.5	C63—C64—H64A	108.6
C13—C22—H22C	109.5	C65—C64—H64A	108.6
H22A—C22—H22C	109.5	C63—C64—H64B	108.6
H22B—C22—H22C	109.5	C65—C64—H64B	108.6
O7—C23—C24	112.1 (8)	H64A—C64—H64B	107.6
O7—C23—H23	123.9	C66—C65—C69	108.0 (4)
C24—C23—H23	123.9	C66—C65—C74	110.7 (3)
C23—C24—C25	102.8 (7)	C69—C65—C74	109.6 (3)
C23—C24—C17	123.5 (7)	C66—C65—C64	108.1 (3)
C25—C24—C17	133.7 (7)	C69—C65—C64	107.7 (3)
C26—C25—C24	114.5 (9)	C74—C65—C64	112.7 (4)
C26—C25—H25	122.8	O18—C66—C67	58.9 (3)
C24—C25—H25	122.8	O18—C66—C58	115.7 (3)
C25—C26—O7	106.7 (8)	C67—C66—C58	120.1 (4)
C25—C26—H26	126.7	O18—C66—C65	109.8 (3)
O7—C26—H26	126.7	C67—C66—C65	116.1 (4)
O9—C27—O8	117.5 (5)	C58—C66—C65	119.9 (4)
O9—C27—C28	121.4 (6)	O18—C67—C66	60.4 (3)
O8—C27—C28	120.7 (5)	O18—C67—C68	118.7 (4)
C29—C28—C27	126.6 (5)	C66—C67—C68	118.2 (4)
C29—C28—H28	116.7	O18—C67—H67	116.0
C27—C28—H28	116.7	C66—C67—H67	116.0
C28—C29—C30	129.9 (4)	C68—C67—H67	116.0
C28—C29—H29	115.1	O20—C68—O19	119.7 (5)
C30—C29—H29	115.1	O20—C68—C67	121.9 (5)
C29—C30—C31	104.6 (3)	O19—C68—C67	118.2 (5)
C29—C30—C44	108.2 (4)	O19—C69—C76	105.1 (4)
C31—C30—C44	114.2 (4)	O19—C69—C65	110.4 (3)
C29—C30—C35	106.3 (3)	C76—C69—C65	115.6 (4)
C31—C30—C35	106.4 (3)	O19—C69—H69	108.5
C44—C30—C35	116.2 (4)	C76—C69—H69	108.5
C37—C31—C30	118.3 (3)	C65—C69—H69	108.5
C37—C31—C32	106.7 (3)	C56—C70—H70A	109.5
C30—C31—C32	117.8 (3)	C56—C70—H70B	109.5
C37—C31—H31	104.0	H70A—C70—H70B	109.5
C30—C31—H31	104.0	C56—C70—H70C	109.5
C32—C31—H31	104.0	H70A—C70—H70C	109.5
C33—C32—C45	107.9 (4)	H70B—C70—H70C	109.5
C33—C32—C31	104.7 (3)	C58—C71—H71A	109.5
C45—C32—C31	114.6 (4)	C58—C71—H71B	109.5
C33—C32—C40	113.5 (4)	H71A—C71—H71B	109.5
C45—C32—C40	107.8 (4)	C58—C71—H71C	109.5
C31—C32—C40	108.5 (3)	H71A—C71—H71C	109.5
O10—C33—C34	121.1 (4)	H71B—C71—H71C	109.5
O10—C33—C32	123.6 (4)	C62—C72—H72A	109.5
C34—C33—C32	115.3 (4)	C62—C72—H72B	109.5
C33—C34—C35	115.1 (4)	H72A—C72—H72B	109.5
C33—C34—H34A	108.5	C62—C72—H72C	109.5
C35—C34—H34A	108.5	H72A—C72—H72C	109.5
C33—C34—H34B	108.5	H72B—C72—H72C	109.5
C35—C34—H34B	108.5	C62—C73—H73A	109.5
H34A—C34—H34B	107.5	C62—C73—H73B	109.5
C34—C35—C36	109.9 (3)	H73A—C73—H73B	109.5
C34—C35—C30	114.2 (3)	C62—C73—H73C	109.5
C36—C35—C30	117.9 (4)	H73A—C73—H73C	109.5
C34—C35—H35	104.4	H73B—C73—H73C	109.5
C36—C35—H35	104.4	C65—C74—H74A	109.5
C30—C35—H35	104.4	C65—C74—H74B	109.5
O8—C36—C47	101.1 (4)	H74A—C74—H74B	109.5
O8—C36—C46	107.0 (4)	C65—C74—H74C	109.5
C47—C36—C46	110.2 (4)	H74A—C74—H74C	109.5
O8—C36—C35	112.4 (3)	H74B—C74—H74C	109.5
C47—C36—C35	115.6 (4)	C76—C75—O21	110.8 (5)
C46—C36—C35	110.0 (4)	C76—C75—H75	124.6
C38—C37—C31	108.2 (4)	O21—C75—H75	124.6
C38—C37—H37A	110.1	C75—C76—C77	106.2 (5)
C31—C37—H37A	110.1	C75—C76—C69	125.0 (5)
C38—C37—H37B	110.1	C77—C76—C69	128.8 (5)
C31—C37—H37B	110.1	C78—C77—C76	107.2 (6)
H37A—C37—H37B	108.4	C78—C77—H77	126.4
C37—C38—C39	114.6 (3)	C76—C77—H77	126.4
C37—C38—H38A	108.6	C77—C78—O21	109.2 (5)
C39—C38—H38A	108.6	C77—C78—H78	125.4
C37—C38—H38B	108.6	O21—C78—H78	125.4
C39—C38—H38B	108.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O1	0.96	2.46	3.041 (7)	119
C22—H22A···O5	0.96	2.55	2.970 (6)	107
C44—H44B···O8	0.96	2.49	3.033 (6)	116
C55—H55···O13	0.93	2.52	3.312 (5)	143
C61—H61···O10	0.97	2.57	3.448 (4)	149
C64—H64B···O13	0.97	2.57	3.403 (6)	144
C70—H70C···O15	0.96	2.56	2.925 (5)	103
C74—H74A···O19	0.96	2.55	2.964 (5)	106
C9—H9···O17ⁱ	0.98	2.53	3.460 (6)	159
C22—H22C···O17ⁱ	0.96	2.58	3.439 (6)	149
C23—H23···O2ⁱⁱ	0.93	2.48	3.188 (8)	133
C37—H37B···O19ⁱ	0.97	2.57	3.424 (5)	147
C37—H37B···O20ⁱ	0.97	2.58	3.299 (5)	131
C72—H72A···O8ⁱⁱⁱ	0.96	2.56	3.409 (7)	148
C73—H73B···O21^iv	0.96	2.55	3.430 (7)	152

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

Puckering parameters (Å, °) for seven- and six-membered rings. top

	q2	q3	φ₂	φ₃	Q	θ₂
Molecule 1
ring A	0.821 (4)	0.273 (4)	-20.1 (3)	75.6 (10)	0.866 (4)	71.6 (3)
ring B	0.053 (4)	0.528 (4)	103 (5)		0.503 (4)	5.8 (4)
ring C	0.755 (5)	-0.102 (5)	-159.5 (3)		0.764 (5)	97.7 (4)
ring D	0.495 (6)	-0.190 (6)	97.4 (6)		0.530 (6)	111.0 (7)
Molecule 2
ring A	0.816 (4)	0.301 (5)	-16.2 (4)	70.8 (8)	0.870 (4)	69.8 (3)
ring B	0.100 (4)	0.527 (4)	87 (3)		0.536 (4)	10.7 (4)
ring C	0.778 (5)	-0.108 (4)	-152.0 (3)		0.786 (5)	97.9 (3)
ring D	0.480 (5)	-0.200 (4)	96.6 (6)		0.520 (5)	112.7 (5)
Molecule 3
ring A	0.901 (4)	0.240 (4)	-36.3 (3)	78.2 (10)	0.932 (4)	75.1 (2)
ring B	0.085 (4)	0.536 (4)	76 (3)		0.542 (4)	9.0 (4)
ring C	0.757 (4)	-0.099 (4)	-154.7 (3)		0.763 (4)	97.5 (3)
ring D	0.537 (4)	-0.166 (4)	95.7 (4)		0.562 (4)	107.2 (4)

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