Structure determination of phase II of the anti­fungal drug griseofulvin by powder X-ray diffraction

Two new crystalline polymorphs of the widely used anti­fungal drug griseofulvin (phases II and III), which originate from the crystallization of the melt, have been detected recently. The crystal structure of phase II of griseofulvin {systematic name: (2S,6′R)-7-chloro-2′,4,6-trimeth­oxy-6′-methyl-3H,4′H-spiro­[1-benzo­furan-2,1′-cyclo­hex-2-ene]-3,4′-dione}, C₁₇H₁₇ClO₆, has been solved by powder X-ray diffraction (PXRD). The PXRD pattern of this new phase was recorded at room temperature using synchrotron radiation. The starting structural model was generated by a Monte Carlo simulated annealing method. The final structure was obtained through Rietveld refinement with soft restraints for inter­atomic bond lengths and angles, except for the aromatic ring, where a rigid-body constraint was applied. The symmetry is ortho­rhom­bic (space group P2₁2₁2₁) and the asymmetric unit contains two mol­ecules.

Computing details

(2S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro[1-benzofuran-2,1'-cyclohex-2-ene]-3,4'-dione

Crystal data

C17H17ClO6	Z = 8
Mr = 352.76	F(000) = 1472
Orthorhombic, P212121	Dx = 1.367 Mg m^−3
Hall symbol: P 2ac 2ab	Synchrotron radiation
a = 11.76250 (11) Å	µ = 1.17 mm^−1
b = 12.00313 (13) Å	T = 293 K
c = 24.2755 (2) Å	white
V = 3427.38 (6) Å^3

Data collection

Powder diffractometer	2θmin = 5°, 2θmax = 59.99°, 2θstep = 0.01°
Data collection mode: transmission

Refinement

Rp = 0.059	132 restraints
Rwp = 0.079	182 constraints
Rexp = 0.058	H-atom parameters constrained
R(F) = 0.099	Weighting scheme based on measured s.u.'s
5500 data points	(Δ/σ)max = 0.038
Excluded region(s): from 11.67 to 11.670	Background function: Manual background combined with 20 Legendre polynoms
Profile function: Pseudo-Voigt	Preferred orientation correction: none
173 parameters

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

	x	y	z	Uiso*/Ueq
C4a	0.1669 (8)	−0.0146 (8)	0.8980 (3)	0.0545 (13)*
C5a	0.0970 (9)	−0.1028 (9)	0.8799 (4)	0.0545 (13)*
C6a	−0.0011 (8)	−0.0815 (8)	0.8467 (3)	0.0545 (13)*
C7a	−0.0292 (6)	0.0287 (8)	0.8317 (3)	0.0545 (13)*
C8a	0.0398 (7)	0.1147 (8)	0.8497 (4)	0.0545 (13)*
C9a	0.1352 (8)	0.0931 (8)	0.8820 (4)	0.0545 (13)*
C3a	0.1889 (12)	0.2005 (8)	0.8930 (7)	0.0545 (13)*
C2a	0.1132 (9)	0.2883 (8)	0.8640 (4)	0.0545 (13)*
C6'a	0.1788 (11)	0.3547 (10)	0.8206 (5)	0.0545 (13)*
C5'a	0.2453 (11)	0.4549 (11)	0.8446 (6)	0.0545 (13)*
C4'a	0.1726 (17)	0.5287 (11)	0.8831 (10)	0.0545 (13)*
C3'a	0.0775 (14)	0.4766 (10)	0.9125 (7)	0.0545 (13)*
C2'a	0.0586 (14)	0.3647 (9)	0.9079 (6)	0.0545 (13)*
O2a	0.2612 (9)	−0.0279 (9)	0.9296 (4)	0.048 (2)*
C12a	0.2973 (18)	−0.1353 (12)	0.9411 (9)	0.0545 (13)*
O4a	−0.0714 (9)	−0.1652 (10)	0.8282 (5)	0.048 (2)*
C13a	−0.0463 (18)	−0.2773 (11)	0.8455 (10)	0.0545 (13)*
Cl1a	−0.1476 (6)	0.0588 (6)	0.7914 (3)	0.0545 (13)*
O1a	0.0258 (10)	0.2249 (9)	0.8359 (6)	0.048 (2)*
O3a	0.2769 (11)	0.2221 (10)	0.9202 (6)	0.048 (2)*
O6a	−0.0192 (13)	0.3071 (10)	0.9388 (6)	0.048 (2)*
C11a	−0.0727 (19)	0.3635 (12)	0.9821 (8)	0.0545 (13)*
O5a	0.1987 (13)	0.6276 (11)	0.8894 (6)	0.048 (2)*
C10a	0.2508 (13)	0.2840 (15)	0.7821 (7)	0.0545 (13)*
H25a	0.217757	0.207412	0.779588	0.0655*
H26a	0.330173	0.279367	0.796685	0.0655*
H27a	0.251936	0.318719	0.744633	0.0655*
H28a	−0.12094	0.310017	1.003352	0.0655*
H29a	−0.121137	0.424548	0.966828	0.0655*
H30a	−0.013847	0.395903	1.007100	0.0655*
H31a	0.318169	−0.173823	0.905955	0.0655*
H32a	0.234618	−0.177272	0.959651	0.0655*
H33a	0.365066	−0.132447	0.965874	0.0655*
H34a	−0.101762	−0.32983	0.828276	0.0655*
H35a	−0.052183	−0.282292	0.886550	0.0655*
H36a	0.032587	−0.29744	0.833809	0.0655*
H37a	0.313372	0.427176	0.865099	0.0655*
H38a	0.276045	0.501287	0.813821	0.0655*
H39a	0.026218	0.523151	0.93593	0.0655*
H40a	0.117815	0.38701	0.796705	0.0655*
H41a	0.116325	−0.181085	0.890388	0.0655*
C4b	0.3427 (8)	0.3003 (8)	0.5995 (4)	0.0545 (13)*
C5b	0.4094 (8)	0.3841 (10)	0.6238 (4)	0.0545 (13)*
C6b	0.4947 (7)	0.3583 (9)	0.6638 (3)	0.0545 (13)*
C7b	0.5110 (6)	0.2456 (8)	0.6787 (3)	0.0545 (13)*
C8b	0.4441 (8)	0.1644 (9)	0.6542 (4)	0.0545 (13)*
C9b	0.3623 (8)	0.1924 (8)	0.6156 (4)	0.0545 (13)*
C3b	0.3112 (13)	0.0885 (8)	0.5969 (7)	0.0545 (13)*
C2b	0.3814 (9)	−0.0043 (8)	0.6249 (4)	0.0545 (13)*
C6'b	0.4546 (10)	−0.0715 (10)	0.5840 (5)	0.0545 (13)*
C5'b	0.3873 (13)	−0.1661 (11)	0.5561 (5)	0.0545 (13)*
C4'b	0.3136 (19)	−0.2355 (11)	0.5964 (7)	0.0545 (13)*
C3'b	0.2665 (15)	−0.1790 (11)	0.6452 (6)	0.0545 (13)*
C2'b	0.3020 (14)	−0.0751 (10)	0.6594 (6)	0.0545 (13)*
O2b	0.2606 (9)	0.3171 (9)	0.5616 (4)	0.048 (2)*
C12b	0.2358 (14)	0.4274 (12)	0.5462 (9)	0.0545 (13)*
O4b	0.5621 (9)	0.4365 (10)	0.6887 (5)	0.048 (2)*
C13b	0.5391 (15)	0.5520 (11)	0.6790 (10)	0.0545 (13)*
Cl1b	0.6117 (6)	0.2041 (6)	0.7267 (3)	0.0545 (13)*
O1b	0.4553 (11)	0.0517 (9)	0.6623 (5)	0.048 (2)*
O3b	0.2323 (12)	0.0734 (10)	0.5640 (6)	0.048 (2)*
O6b	0.2615 (13)	−0.0165 (10)	0.7039 (6)	0.048 (2)*
C11b	0.1727 (15)	−0.0687 (14)	0.7344 (8)	0.0545 (13)*
O5b	0.2920 (14)	−0.3338 (10)	0.5858 (6)	0.048 (2)*
C10b	0.5175 (15)	0.0019 (15)	0.5410 (7)	0.0545 (13)*
H25b	0.594901	0.021226	0.55512	0.0655*
H26b	0.524864	−0.039997	0.505551	0.0655*
H27b	0.473252	0.071871	0.534537	0.0655*
H28b	0.142271	−0.015394	0.762348	0.0655*
H29b	0.110277	−0.091239	0.70869	0.0655*
H30b	0.203261	−0.13627	0.753412	0.0655*
H31b	0.239949	0.476713	0.579336	0.0655*
H32b	0.292129	0.453025	0.518110	0.0655*
H33b	0.157446	0.430859	0.530211	0.0655*
H34b	0.458768	0.568923	0.689663	0.0655*
H35b	0.592021	0.598518	0.701585	0.0655*
H36b	0.550316	0.56911	0.639092	0.0655*
H37b	0.440979	−0.216494	0.536203	0.0655*
H38b	0.337822	−0.13426	0.526558	0.0655*
H39b	0.207766	−0.217472	0.668074	0.0655*
H40b	0.515327	−0.106748	0.607015	0.0655*
H41b	0.396967	0.46347	0.612865	0.0655*

Geometric parameters (Å, º)

C2a—C6'a	1.530 (15)	C2b—C6'b	1.542 (16)
C2a—C2'a	1.545 (17)	C2b—C2'b	1.515 (17)
C2a—O1a	1.450 (16)	C2b—O1b	1.424 (15)
C3a—C2a	1.549 (16)	C3b—C2b	1.544 (16)
C3a—O3a	1.26 (2)	C3b—O3b	1.24 (2)
C4a—C5a	1.410 (14)	C4b—C5b	1.404 (14)
C4a—C9a	1.401 (14)	C4b—C9b	1.372 (14)
C4a—O2a	1.357 (13)	C4b—O2b	1.350 (14)
C5a—C6a	1.431 (13)	C5b—C6b	1.430 (13)
C5a—H41a	1	C5b—H41b	1
C6a—C7a	1.411 (14)	C6b—C7b	1.413 (14)
C6a—O4a	1.376 (15)	C6b—O4b	1.369 (15)
C7a—C8a	1.383 (13)	C7b—C8b	1.387 (13)
C8a—C9a	1.393 (13)	C8b—C9b	1.384 (13)
C8a—O1a	1.375 (15)	C8b—O1b	1.374 (15)
C9a—C3a	1.460 (15)	C9b—C3b	1.457 (15)
C2'a—O6a	1.37 (2)	C2'b—O6b	1.373 (19)
C3'a—C2'a	1.365 (17)	C3'b—C2'b	1.360 (19)
C3'a—H39a	1	C3'b—H39b	1
C4'a—C3'a	1.47 (3)	C4'b—C3'b	1.47 (2)
C4'a—O5a	1.24 (2)	C4'b—O5b	1.234 (19)
C5'a—C4'a	1.54 (2)	C5'b—C4'b	1.55 (2)
C5'a—H37a	1	C5'b—H37b	1
C5'a—H38a	1	C5'b—H38b	1
C6'a—C5'a	1.549 (18)	C6'b—C5'b	1.541 (18)
C6'a—C10a	1.52 (2)	C6'b—C10b	1.55 (2)
C6'a—H40a	1	C6'b—H40b	1
O2a—C12a	1.386 (19)	O2b—C12b	1.406 (19)
C12a—H31a	1	C12b—H31b	1
C12a—H32a	1	C12b—H32b	1
C12a—H33a	1	C12b—H33b	1
O4a—C13a	1.440 (19)	O4b—C13b	1.432 (18)
C13a—H34a	1	C13b—H34b	1
C13a—H35a	1	C13b—H35b	1
C13a—H36a	1	C13b—H36b	1
O6a—C11a	1.40 (2)	O6b—C11b	1.43 (2)
C7a—Cl1a	1.740 (1)	C11b—H28b	1
C11a—H28a	1	C11b—H29b	1
C11a—H29a	1	C11b—H30b	1
C11a—H30a	1	C10b—H25b	1
C10a—H25a	1	C10b—H26b	1
C10a—H26a	1	C10b—H27b	1
C10a—H27a	1	C7b—Cl1b	1.730 (1)
C5a—C4a—C9a	116.8 (8)	C5b—C4b—C9b	117.5 (9)
C5a—C4a—O2a	124.4 (10)	C5b—C4b—O2b	125.4 (10)
C9a—C4a—O2a	118.9 (9)	C9b—C4b—O2b	117.0 (9)
C4a—C5a—C6a	120.8 (9)	C4b—C5b—C6b	121.5 (10)
C4a—C5a—H41a	119.6	C4b—C5b—H41b	119.27
C6a—C5a—H41a	119.6	C6b—C5b—H41b	119.27
C5a—C6a—C7a	120.1 (9)	C5b—C6b—C7b	118.4 (8)
C5a—C6a—O4a	122.5 (10)	C5b—C6b—O4b	123.9 (10)
C7a—C6a—O4a	117.4 (8)	C7b—C6b—O4b	117.7 (8)
C6a—C7a—C8a	118.7 (7)	C6b—C7b—C8b	119.1 (7)
C7a—C8a—C9a	120.8 (9)	C7b—C8b—C9b	120.9 (9)
C7a—C8a—O1a	124.8 (9)	C7b—C8b—O1b	125.2 (9)
C9a—C8a—O1a	114.3 (9)	C9b—C8b—O1b	113.7 (9)
C4a—C9a—C8a	122.8 (9)	C4b—C9b—C8b	122.6 (9)
C4a—C9a—C3a	130.5 (10)	C4b—C9b—C3b	130.6 (10)
C8a—C9a—C3a	106.7 (9)	C8b—C9b—C3b	106.8 (10)
C9a—C3a—C2a	105.6 (11)	C9b—C3b—C2b	105.1 (11)
C9a—C3a—O3a	129.4 (12)	C9b—C3b—O3b	129.5 (11)
C2a—C3a—O3a	124.9 (10)	C2b—C3b—O3b	125.4 (10)
C3a—C2a—C6'a	112.2 (9)	C3b—C2b—C6'b	113.1 (9)
C3a—C2a—C2'a	109.3 (10)	C3b—C2b—C2'b	108.5 (10)
C3a—C2a—O1a	105.3 (9)	C3b—C2b—O1b	105.4 (9)
C6'a—C2a—C2'a	112.0 (9)	C6'b—C2b—C2'b	114.0 (9)
C6'a—C2a—O1a	107.8 (9)	C6'b—C2b—O1b	108.4 (9)
C2'a—C2a—O1a	110.0 (10)	C2'b—C2b—O1b	106.8 (9)
C2a—C6'a—C5'a	113.5 (10)	C2b—C6'b—C5'b	112.4 (10)
C2a—C6'a—C10a	114.5 (10)	C2b—C6'b—C10b	113.7 (10)
C2a—C6'a—H40a	103.89	C2b—C6'b—H40b	105.07
C5'a—C6'a—C10a	112.6 (11)	C5'b—C6'b—C10b	111.6 (11)
C5'a—C6'a—H40a	106.21	C5'b—C6'b—H40b	107.52
C10a—C6'a—H40a	105.06	C10b—C6'b—H40b	106
C6'a—C5'a—C4'a	113.2 (11)	C6'b—C5'b—C4'b	114.0 (11)
C6'a—C5'a—H37a	109.47	C6'b—C5'b—H37b	109.47
C6'a—C5'a—H38a	109.47	C6'b—C5'b—H38b	109.47
C4'a—C5'a—H37a	109.47	C4'b—C5'b—H37b	109.47
C4'a—C5'a—H38a	109.47	C4'b—C5'b—H38b	109.47
H37a—C5'a—H38a	105.47	H37b—C5'b—H38b	104.52
C5'a—C4'a—C3'a	118.1 (12)	C5'b—C4'b—C3'b	118.0 (11)
C5'a—C4'a—O5a	119.2 (17)	C5'b—C4'b—O5b	119.9 (15)
C3'a—C4'a—O5a	122.6 (18)	C3'b—C4'b—O5b	122.0 (16)
C4'a—C3'a—C2'a	120.2 (15)	C4'b—C3'b—C2'b	120.8 (14)
C4'a—C3'a—H39a	119.9	C4'b—C3'b—H39b	119.61
C2'a—C3'a—H39a	119.9	C2'b—C3'b—H39b	119.61
C2a—C2'a—C3'a	124.9 (14)	C2b—C2'b—C3'b	124.2 (13)
C2a—C2'a—O6a	110.8 (10)	C2b—C2'b—O6b	111.2 (11)
C3'a—C2'a—O6a	124.0 (14)	C3'b—C2'b—O6b	124.3 (14)
C4a—O2a—C12a	118.2 (12)	C4b—O2b—C12b	118.0 (12)
O2a—C12a—H31a	109.47	O2b—C12b—H31b	109.47
O2a—C12a—H32a	109.47	O2b—C12b—H32b	109.47
O2a—C12a—H33a	109.47	O2b—C12b—H33b	109.47
H31a—C12a—H32a	109.47	H31b—C12b—H32b	109.47
H31a—C12a—H33a	109.47	H31b—C12b—H33b	109.47
H32a—C12a—H33a	109.47	H32b—C12b—H33b	109.47
C6a—O4a—C13a	117.6 (12)	C6b—O4b—C13b	118.8 (12)
O4a—C13a—H34a	109.47	O4b—C13b—H34b	109.47
O4a—C13a—H35a	109.47	O4b—C13b—H35b	109.47
O4a—C13a—H36a	109.47	O4b—C13b—H36b	109.47
H34a—C13a—H35a	109.47	H34b—C13b—H35b	109.47
H34a—C13a—H36a	109.47	H34b—C13b—H36b	109.47
H35a—C13a—H36a	109.47	H35b—C13b—H36b	109.47
C8a—O1a—C2a	107.8 (10)	C8b—O1b—C2b	108.4 (9)
C2'a—O6a—C11a	117.9 (13)	C2'b—O6b—C11b	115.9 (13)
O6a—C11a—H28a	109.47	O6b—C11b—H28b	109.47
O6a—C11a—H29a	109.47	O6b—C11b—H29b	109.47
O6a—C11a—H30a	109.47	O6b—C11b—H30b	109.47
H28a—C11a—H29a	109.47	H28b—C11b—H29b	109.47
H28a—C11a—H30a	109.47	H28b—C11b—H30b	109.47
H29a—C11a—H30a	109.47	H29b—C11b—H30b	109.47
C6'a—C10a—H25a	109.47	C6'b—C10b—H25b	109.47
C6'a—C10a—H26a	109.47	C6'b—C10b—H26b	109.47
C6'a—C10a—H27a	109.47	C6'b—C10b—H27b	109.47
H25a—C10a—H26a	109.47	H25b—C10b—H26b	109.47
H25a—C10a—H27a	109.47	H25b—C10b—H27b	109.47
H26a—C10a—H27a	109.47	H26b—C10b—H27b	109.47
C6a—C7a—Cl1a	121.8 (7)	C6b—C7b—Cl1b	122.6 (7)
C8a—C7a—Cl1a	119.5 (7)	C8b—C7b—Cl1b	118.3 (7)
C9a—C4a—C5a—C6a	0.1 (13)	O2b—C4b—C9b—C8b	−179.9 (9)
O2a—C4a—C5a—C6a	179.9 (9)	O2b—C4b—C9b—C3b	2.5 (17)
C5a—C4a—C9a—C8a	−0.1 (13)	C5b—C4b—O2b—C12b	−2.6 (17)
C5a—C4a—C9a—C3a	−179.1 (12)	C9b—C4b—O2b—C12b	177.4 (12)
O2a—C4a—C9a—C8a	−179.9 (9)	C4b—C5b—C6b—C7b	0.00 (16)
O2a—C4a—C9a—C3a	0.9 (17)	C4b—C5b—C6b—O4b	179.9 (9)
C5a—C4a—O2a—C12a	5.6 (17)	C5b—C6b—C7b—C8b	0.00 (3)
C9a—C4a—O2a—C12a	−174.3 (13)	C5b—C6b—C7b—Cl1b	−180.00 (4)
C4a—C5a—C6a—C7a	−0.1 (13)	O4b—C6b—C7b—C8b	−180.00 (3)
C4a—C5a—C6a—O4a	−180.00 (5)	O4b—C6b—C7b—Cl1b	0.1 (11)
C5a—C6a—C7a—C8a	0.00 (2)	C5b—C6b—O4b—C13b	6.9 (17)
C5a—C6a—C7a—Cl1a	−180.00 (4)	C7b—C6b—O4b—C13b	−173.2 (12)
O4a—C6a—C7a—C8a	180.00 (13)	C6b—C7b—C8b—C9b	0.1 (13)
O4a—C6a—C7a—Cl1a	−0.1 (11)	C6b—C7b—C8b—O1b	175.9 (9)
C5a—C6a—O4a—C13a	2.9 (17)	Cl1b—C7b—C8b—C9b	−180.00 (3)
C7a—C6a—O4a—C13a	−177.1 (12)	Cl1b—C7b—C8b—O1b	−4.1 (13)
C6a—C7a—C8a—C9a	0.00 (10)	C7b—C8b—C9b—C4b	0.00 (13)
C6a—C7a—C8a—O1a	176.6 (9)	C7b—C8b—C9b—C3b	178.0 (10)
Cl1a—C7a—C8a—C9a	−180.00 (4)	O1b—C8b—C9b—C4b	−176.3 (9)
Cl1a—C7a—C8a—O1a	−3.4 (13)	O1b—C8b—C9b—C3b	1.7 (13)
C7a—C8a—C9a—C4a	0.00 (10)	C7b—C8b—O1b—C2b	−172.7 (9)
C7a—C8a—C9a—C3a	179.3 (10)	C9b—C8b—O1b—C2b	3.4 (13)
O1a—C8a—C9a—C4a	−176.9 (10)	C4b—C9b—C3b—C2b	172.2 (10)
O1a—C8a—C9a—C3a	2.4 (13)	C4b—C9b—C3b—O3b	−5 (3)
C7a—C8a—O1a—C2a	178.6 (9)	C8b—C9b—C3b—C2b	−5.6 (13)
C9a—C8a—O1a—C2a	−4.6 (13)	C8b—C9b—C3b—O3b	177.5 (16)
C4a—C9a—C3a—C2a	180.0 (3)	C9b—C3b—C2b—C6'b	−110.8 (11)
C4a—C9a—C3a—O3a	−1 (3)	C9b—C3b—C2b—C2'b	121.6 (11)
C8a—C9a—C3a—C2a	0.8 (13)	C9b—C3b—C2b—O1b	7.5 (13)
C8a—C9a—C3a—O3a	−179.9 (16)	O3b—C3b—C2b—C6'b	66.3 (19)
C9a—C3a—C2a—C6'a	−120.3 (11)	O3b—C3b—C2b—C2'b	−61.3 (19)
C9a—C3a—C2a—C2'a	114.8 (12)	O3b—C3b—C2b—O1b	−175.4 (15)
C9a—C3a—C2a—O1a	−3.3 (13)	C3b—C2b—C6'b—C5'b	−84.2 (12)
O3a—C3a—C2a—C6'a	60.4 (19)	C3b—C2b—C6'b—C10b	43.7 (14)
O3a—C3a—C2a—C2'a	−64.5 (19)	C2'b—C2b—C6'b—C5'b	40.5 (14)
O3a—C3a—C2a—O1a	177.4 (15)	C2'b—C2b—C6'b—C10b	168.4 (11)
C3a—C2a—C6'a—C5'a	−84.4 (12)	O1b—C2b—C6'b—C5'b	159.3 (10)
C3a—C2a—C6'a—C10a	46.7 (14)	O1b—C2b—C6'b—C10b	−72.8 (13)
C2'a—C2a—C6'a—C5'a	39.0 (14)	C3b—C2b—C2'b—C4'b	108.6 (9)
C2'a—C2a—C6'a—C10a	170.1 (11)	C3b—C2b—C2'b—C3'b	105.3 (16)
O1a—C2a—C6'a—C5'a	160.1 (10)	C3b—C2b—C2'b—O6b	−68.4 (14)
O1a—C2a—C6'a—C10a	−68.8 (13)	C6'b—C2b—C2'b—C4'b	−18.5 (11)
C3a—C2a—C2'a—C3'a	116.9 (16)	C6'b—C2b—C2'b—C3'b	−21.8 (19)
C3a—C2a—C2'a—O6a	−68.4 (15)	C6'b—C2b—C2'b—O6b	164.5 (11)
C3a—C2a—C2'a—C11a	−66 (2)	O1b—C2b—C2'b—C4'b	−138.3 (9)
C6'a—C2a—C2'a—C3'a	−8 (2)	O1b—C2b—C2'b—C3'b	−141.5 (15)
C6'a—C2a—C2'a—O6a	166.7 (12)	O1b—C2b—C2'b—O6b	44.7 (15)
C6'a—C2a—C2'a—C11a	169.0 (15)	C3b—C2b—O1b—C8b	−6.7 (13)
O1a—C2a—C2'a—C3'a	−128.0 (16)	C6'b—C2b—O1b—C8b	114.7 (10)
O1a—C2a—C2'a—O6a	46.8 (15)	C2'b—C2b—O1b—C8b	−122.0 (10)
O1a—C2a—C2'a—C11a	49 (2)	C2b—C6'b—C5'b—C4'b	−45.5 (15)
C3a—C2a—O1a—C8a	4.7 (13)	C10b—C6'b—C5'b—C4'b	−174.5 (13)
C6'a—C2a—O1a—C8a	124.6 (10)	C6'b—C5'b—C4'b—C3'b	31 (2)
C2'a—C2a—O1a—C8a	−113.0 (10)	C6'b—C5'b—C4'b—C2'b	26.0 (13)
C2a—C6'a—C5'a—C4'a	−48.9 (16)	C6'b—C5'b—C4'b—O5b	−151.9 (17)
C10a—C6'a—C5'a—C4'a	179.1 (13)	C5'b—C4'b—C3'b—C2'b	−11 (2)
C6'a—C5'a—C4'a—C3'a	28 (2)	O5b—C4'b—C3'b—C2'b	172.2 (18)
C6'a—C5'a—C4'a—O5a	−154.8 (17)	C5'b—C4'b—C2'b—C2b	−4.4 (12)
C5'a—C4'a—C3'a—C2'a	4 (3)	C5'b—C4'b—C2'b—C3'b	170 (2)
O5a—C4'a—C3'a—C2'a	−174.0 (19)	C5'b—C4'b—C2'b—O6b	169 (3)
C4'a—C3'a—C2'a—C2a	−14 (3)	C3'b—C4'b—C2'b—C2b	−175 (2)
C4'a—C3'a—C2'a—O6a	171.8 (17)	C3'b—C4'b—C2'b—O6b	−1 (3)
C4'a—C3'a—C2'a—C11a	167.7 (16)	O5b—C4'b—C2'b—C2b	172 (3)
C2a—C2'a—O6a—C11a	177.2 (14)	O5b—C4'b—C2'b—C3'b	−13 (3)
C3'a—C2'a—O6a—C11a	−8 (3)	O5b—C4'b—C2'b—O6b	−15 (5)
C2a—C2'a—C11a—O6a	−4 (2)	C4'b—C3'b—C2'b—C2b	6 (2)
C3'a—C2'a—C11a—O6a	173 (2)	C4'b—C3'b—C2'b—O6b	179.3 (15)
C9b—C4b—C5b—C6b	0.1 (14)	C2b—C2'b—O6b—C11b	170.6 (12)
O2b—C4b—C5b—C6b	179.9 (9)	C4'b—C2'b—O6b—C11b	−2 (4)
C5b—C4b—C9b—C8b	0.0000 (18)	C3'b—C2'b—O6b—C11b	−3 (2)
C5b—C4b—C9b—C3b	−177.5 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13a—H36a···O5a^i	1.00	2.54	3.28 (3)	130.00
C5a—H41a···O5a^i	1.00	2.49	3.459 (18)	162.17
C11a—H28a···O3a^ii	1.00	2.24	3.13 (2)	147.00
C11a—H29a···O3b^iii	1.00	2.34	3.34 (2)	177.00

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