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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618001845/cu3124sup1.cif
Contains datablocks Griseofulvin_Phase_II, I

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2053229618001845/cu3124Isup2.rtv
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618001845/cu3124sup3.pdf
The reduced coordinates for the non-H atoms of phase II

CCDC reference: 1820716

Computing details top

(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 top
Crystal data top
C17H17ClO6Z = 8
Mr = 352.76F(000) = 1472
Orthorhombic, P212121Dx = 1.367 Mg m3
Hall symbol: P 2ac 2abSynchrotron radiation
a = 11.76250 (11) ŵ = 1.17 mm1
b = 12.00313 (13) ÅT = 293 K
c = 24.2755 (2) Åwhite
V = 3427.38 (6) Å3
Data collection top
Powder
diffractometer
2θmin = 5°, 2θmax = 59.99°, 2θstep = 0.01°
Data collection mode: transmission
Refinement top
Rp = 0.059132 restraints
Rwp = 0.079182 constraints
Rexp = 0.058H-atom parameters constrained
R(F) = 0.099Weighting scheme based on measured s.u.'s
5500 data points(Δ/σ)max = 0.038
Excluded region(s): from 11.67 to 11.670Background function: Manual background combined with 20 Legendre polynoms
Profile function: Pseudo-VoigtPreferred orientation correction: none
173 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C4a0.1669 (8)0.0146 (8)0.8980 (3)0.0545 (13)*
C5a0.0970 (9)0.1028 (9)0.8799 (4)0.0545 (13)*
C6a0.0011 (8)0.0815 (8)0.8467 (3)0.0545 (13)*
C7a0.0292 (6)0.0287 (8)0.8317 (3)0.0545 (13)*
C8a0.0398 (7)0.1147 (8)0.8497 (4)0.0545 (13)*
C9a0.1352 (8)0.0931 (8)0.8820 (4)0.0545 (13)*
C3a0.1889 (12)0.2005 (8)0.8930 (7)0.0545 (13)*
C2a0.1132 (9)0.2883 (8)0.8640 (4)0.0545 (13)*
C6'a0.1788 (11)0.3547 (10)0.8206 (5)0.0545 (13)*
C5'a0.2453 (11)0.4549 (11)0.8446 (6)0.0545 (13)*
C4'a0.1726 (17)0.5287 (11)0.8831 (10)0.0545 (13)*
C3'a0.0775 (14)0.4766 (10)0.9125 (7)0.0545 (13)*
C2'a0.0586 (14)0.3647 (9)0.9079 (6)0.0545 (13)*
O2a0.2612 (9)0.0279 (9)0.9296 (4)0.048 (2)*
C12a0.2973 (18)0.1353 (12)0.9411 (9)0.0545 (13)*
O4a0.0714 (9)0.1652 (10)0.8282 (5)0.048 (2)*
C13a0.0463 (18)0.2773 (11)0.8455 (10)0.0545 (13)*
Cl1a0.1476 (6)0.0588 (6)0.7914 (3)0.0545 (13)*
O1a0.0258 (10)0.2249 (9)0.8359 (6)0.048 (2)*
O3a0.2769 (11)0.2221 (10)0.9202 (6)0.048 (2)*
O6a0.0192 (13)0.3071 (10)0.9388 (6)0.048 (2)*
C11a0.0727 (19)0.3635 (12)0.9821 (8)0.0545 (13)*
O5a0.1987 (13)0.6276 (11)0.8894 (6)0.048 (2)*
C10a0.2508 (13)0.2840 (15)0.7821 (7)0.0545 (13)*
H25a0.2177570.2074120.7795880.0655*
H26a0.3301730.2793670.7966850.0655*
H27a0.2519360.3187190.7446330.0655*
H28a0.120940.3100171.0033520.0655*
H29a0.1211370.4245480.9668280.0655*
H30a0.0138470.3959031.0071000.0655*
H31a0.3181690.1738230.9059550.0655*
H32a0.2346180.1772720.9596510.0655*
H33a0.3650660.1324470.9658740.0655*
H34a0.1017620.329830.8282760.0655*
H35a0.0521830.2822920.8865500.0655*
H36a0.0325870.297440.8338090.0655*
H37a0.3133720.4271760.8650990.0655*
H38a0.2760450.5012870.8138210.0655*
H39a0.0262180.5231510.935930.0655*
H40a0.1178150.387010.7967050.0655*
H41a0.1163250.1810850.8903880.0655*
C4b0.3427 (8)0.3003 (8)0.5995 (4)0.0545 (13)*
C5b0.4094 (8)0.3841 (10)0.6238 (4)0.0545 (13)*
C6b0.4947 (7)0.3583 (9)0.6638 (3)0.0545 (13)*
C7b0.5110 (6)0.2456 (8)0.6787 (3)0.0545 (13)*
C8b0.4441 (8)0.1644 (9)0.6542 (4)0.0545 (13)*
C9b0.3623 (8)0.1924 (8)0.6156 (4)0.0545 (13)*
C3b0.3112 (13)0.0885 (8)0.5969 (7)0.0545 (13)*
C2b0.3814 (9)0.0043 (8)0.6249 (4)0.0545 (13)*
C6'b0.4546 (10)0.0715 (10)0.5840 (5)0.0545 (13)*
C5'b0.3873 (13)0.1661 (11)0.5561 (5)0.0545 (13)*
C4'b0.3136 (19)0.2355 (11)0.5964 (7)0.0545 (13)*
C3'b0.2665 (15)0.1790 (11)0.6452 (6)0.0545 (13)*
C2'b0.3020 (14)0.0751 (10)0.6594 (6)0.0545 (13)*
O2b0.2606 (9)0.3171 (9)0.5616 (4)0.048 (2)*
C12b0.2358 (14)0.4274 (12)0.5462 (9)0.0545 (13)*
O4b0.5621 (9)0.4365 (10)0.6887 (5)0.048 (2)*
C13b0.5391 (15)0.5520 (11)0.6790 (10)0.0545 (13)*
Cl1b0.6117 (6)0.2041 (6)0.7267 (3)0.0545 (13)*
O1b0.4553 (11)0.0517 (9)0.6623 (5)0.048 (2)*
O3b0.2323 (12)0.0734 (10)0.5640 (6)0.048 (2)*
O6b0.2615 (13)0.0165 (10)0.7039 (6)0.048 (2)*
C11b0.1727 (15)0.0687 (14)0.7344 (8)0.0545 (13)*
O5b0.2920 (14)0.3338 (10)0.5858 (6)0.048 (2)*
C10b0.5175 (15)0.0019 (15)0.5410 (7)0.0545 (13)*
H25b0.5949010.0212260.555120.0655*
H26b0.5248640.0399970.5055510.0655*
H27b0.4732520.0718710.5345370.0655*
H28b0.1422710.0153940.7623480.0655*
H29b0.1102770.0912390.708690.0655*
H30b0.2032610.136270.7534120.0655*
H31b0.2399490.4767130.5793360.0655*
H32b0.2921290.4530250.5181100.0655*
H33b0.1574460.4308590.5302110.0655*
H34b0.4587680.5689230.6896630.0655*
H35b0.5920210.5985180.7015850.0655*
H36b0.5503160.569110.6390920.0655*
H37b0.4409790.2164940.5362030.0655*
H38b0.3378220.134260.5265580.0655*
H39b0.2077660.2174720.6680740.0655*
H40b0.5153270.1067480.6070150.0655*
H41b0.3969670.463470.6128650.0655*
Geometric parameters (Å, º) top
C2a—C6'a1.530 (15)C2b—C6'b1.542 (16)
C2a—C2'a1.545 (17)C2b—C2'b1.515 (17)
C2a—O1a1.450 (16)C2b—O1b1.424 (15)
C3a—C2a1.549 (16)C3b—C2b1.544 (16)
C3a—O3a1.26 (2)C3b—O3b1.24 (2)
C4a—C5a1.410 (14)C4b—C5b1.404 (14)
C4a—C9a1.401 (14)C4b—C9b1.372 (14)
C4a—O2a1.357 (13)C4b—O2b1.350 (14)
C5a—C6a1.431 (13)C5b—C6b1.430 (13)
C5a—H41a1C5b—H41b1
C6a—C7a1.411 (14)C6b—C7b1.413 (14)
C6a—O4a1.376 (15)C6b—O4b1.369 (15)
C7a—C8a1.383 (13)C7b—C8b1.387 (13)
C8a—C9a1.393 (13)C8b—C9b1.384 (13)
C8a—O1a1.375 (15)C8b—O1b1.374 (15)
C9a—C3a1.460 (15)C9b—C3b1.457 (15)
C2'a—O6a1.37 (2)C2'b—O6b1.373 (19)
C3'a—C2'a1.365 (17)C3'b—C2'b1.360 (19)
C3'a—H39a1C3'b—H39b1
C4'a—C3'a1.47 (3)C4'b—C3'b1.47 (2)
C4'a—O5a1.24 (2)C4'b—O5b1.234 (19)
C5'a—C4'a1.54 (2)C5'b—C4'b1.55 (2)
C5'a—H37a1C5'b—H37b1
C5'a—H38a1C5'b—H38b1
C6'a—C5'a1.549 (18)C6'b—C5'b1.541 (18)
C6'a—C10a1.52 (2)C6'b—C10b1.55 (2)
C6'a—H40a1C6'b—H40b1
O2a—C12a1.386 (19)O2b—C12b1.406 (19)
C12a—H31a1C12b—H31b1
C12a—H32a1C12b—H32b1
C12a—H33a1C12b—H33b1
O4a—C13a1.440 (19)O4b—C13b1.432 (18)
C13a—H34a1C13b—H34b1
C13a—H35a1C13b—H35b1
C13a—H36a1C13b—H36b1
O6a—C11a1.40 (2)O6b—C11b1.43 (2)
C7a—Cl1a1.740 (1)C11b—H28b1
C11a—H28a1C11b—H29b1
C11a—H29a1C11b—H30b1
C11a—H30a1C10b—H25b1
C10a—H25a1C10b—H26b1
C10a—H26a1C10b—H27b1
C10a—H27a1C7b—Cl1b1.730 (1)
C5a—C4a—C9a116.8 (8)C5b—C4b—C9b117.5 (9)
C5a—C4a—O2a124.4 (10)C5b—C4b—O2b125.4 (10)
C9a—C4a—O2a118.9 (9)C9b—C4b—O2b117.0 (9)
C4a—C5a—C6a120.8 (9)C4b—C5b—C6b121.5 (10)
C4a—C5a—H41a119.6C4b—C5b—H41b119.27
C6a—C5a—H41a119.6C6b—C5b—H41b119.27
C5a—C6a—C7a120.1 (9)C5b—C6b—C7b118.4 (8)
C5a—C6a—O4a122.5 (10)C5b—C6b—O4b123.9 (10)
C7a—C6a—O4a117.4 (8)C7b—C6b—O4b117.7 (8)
C6a—C7a—C8a118.7 (7)C6b—C7b—C8b119.1 (7)
C7a—C8a—C9a120.8 (9)C7b—C8b—C9b120.9 (9)
C7a—C8a—O1a124.8 (9)C7b—C8b—O1b125.2 (9)
C9a—C8a—O1a114.3 (9)C9b—C8b—O1b113.7 (9)
C4a—C9a—C8a122.8 (9)C4b—C9b—C8b122.6 (9)
C4a—C9a—C3a130.5 (10)C4b—C9b—C3b130.6 (10)
C8a—C9a—C3a106.7 (9)C8b—C9b—C3b106.8 (10)
C9a—C3a—C2a105.6 (11)C9b—C3b—C2b105.1 (11)
C9a—C3a—O3a129.4 (12)C9b—C3b—O3b129.5 (11)
C2a—C3a—O3a124.9 (10)C2b—C3b—O3b125.4 (10)
C3a—C2a—C6'a112.2 (9)C3b—C2b—C6'b113.1 (9)
C3a—C2a—C2'a109.3 (10)C3b—C2b—C2'b108.5 (10)
C3a—C2a—O1a105.3 (9)C3b—C2b—O1b105.4 (9)
C6'a—C2a—C2'a112.0 (9)C6'b—C2b—C2'b114.0 (9)
C6'a—C2a—O1a107.8 (9)C6'b—C2b—O1b108.4 (9)
C2'a—C2a—O1a110.0 (10)C2'b—C2b—O1b106.8 (9)
C2a—C6'a—C5'a113.5 (10)C2b—C6'b—C5'b112.4 (10)
C2a—C6'a—C10a114.5 (10)C2b—C6'b—C10b113.7 (10)
C2a—C6'a—H40a103.89C2b—C6'b—H40b105.07
C5'a—C6'a—C10a112.6 (11)C5'b—C6'b—C10b111.6 (11)
C5'a—C6'a—H40a106.21C5'b—C6'b—H40b107.52
C10a—C6'a—H40a105.06C10b—C6'b—H40b106
C6'a—C5'a—C4'a113.2 (11)C6'b—C5'b—C4'b114.0 (11)
C6'a—C5'a—H37a109.47C6'b—C5'b—H37b109.47
C6'a—C5'a—H38a109.47C6'b—C5'b—H38b109.47
C4'a—C5'a—H37a109.47C4'b—C5'b—H37b109.47
C4'a—C5'a—H38a109.47C4'b—C5'b—H38b109.47
H37a—C5'a—H38a105.47H37b—C5'b—H38b104.52
C5'a—C4'a—C3'a118.1 (12)C5'b—C4'b—C3'b118.0 (11)
C5'a—C4'a—O5a119.2 (17)C5'b—C4'b—O5b119.9 (15)
C3'a—C4'a—O5a122.6 (18)C3'b—C4'b—O5b122.0 (16)
C4'a—C3'a—C2'a120.2 (15)C4'b—C3'b—C2'b120.8 (14)
C4'a—C3'a—H39a119.9C4'b—C3'b—H39b119.61
C2'a—C3'a—H39a119.9C2'b—C3'b—H39b119.61
C2a—C2'a—C3'a124.9 (14)C2b—C2'b—C3'b124.2 (13)
C2a—C2'a—O6a110.8 (10)C2b—C2'b—O6b111.2 (11)
C3'a—C2'a—O6a124.0 (14)C3'b—C2'b—O6b124.3 (14)
C4a—O2a—C12a118.2 (12)C4b—O2b—C12b118.0 (12)
O2a—C12a—H31a109.47O2b—C12b—H31b109.47
O2a—C12a—H32a109.47O2b—C12b—H32b109.47
O2a—C12a—H33a109.47O2b—C12b—H33b109.47
H31a—C12a—H32a109.47H31b—C12b—H32b109.47
H31a—C12a—H33a109.47H31b—C12b—H33b109.47
H32a—C12a—H33a109.47H32b—C12b—H33b109.47
C6a—O4a—C13a117.6 (12)C6b—O4b—C13b118.8 (12)
O4a—C13a—H34a109.47O4b—C13b—H34b109.47
O4a—C13a—H35a109.47O4b—C13b—H35b109.47
O4a—C13a—H36a109.47O4b—C13b—H36b109.47
H34a—C13a—H35a109.47H34b—C13b—H35b109.47
H34a—C13a—H36a109.47H34b—C13b—H36b109.47
H35a—C13a—H36a109.47H35b—C13b—H36b109.47
C8a—O1a—C2a107.8 (10)C8b—O1b—C2b108.4 (9)
C2'a—O6a—C11a117.9 (13)C2'b—O6b—C11b115.9 (13)
O6a—C11a—H28a109.47O6b—C11b—H28b109.47
O6a—C11a—H29a109.47O6b—C11b—H29b109.47
O6a—C11a—H30a109.47O6b—C11b—H30b109.47
H28a—C11a—H29a109.47H28b—C11b—H29b109.47
H28a—C11a—H30a109.47H28b—C11b—H30b109.47
H29a—C11a—H30a109.47H29b—C11b—H30b109.47
C6'a—C10a—H25a109.47C6'b—C10b—H25b109.47
C6'a—C10a—H26a109.47C6'b—C10b—H26b109.47
C6'a—C10a—H27a109.47C6'b—C10b—H27b109.47
H25a—C10a—H26a109.47H25b—C10b—H26b109.47
H25a—C10a—H27a109.47H25b—C10b—H27b109.47
H26a—C10a—H27a109.47H26b—C10b—H27b109.47
C6a—C7a—Cl1a121.8 (7)C6b—C7b—Cl1b122.6 (7)
C8a—C7a—Cl1a119.5 (7)C8b—C7b—Cl1b118.3 (7)
C9a—C4a—C5a—C6a0.1 (13)O2b—C4b—C9b—C8b179.9 (9)
O2a—C4a—C5a—C6a179.9 (9)O2b—C4b—C9b—C3b2.5 (17)
C5a—C4a—C9a—C8a0.1 (13)C5b—C4b—O2b—C12b2.6 (17)
C5a—C4a—C9a—C3a179.1 (12)C9b—C4b—O2b—C12b177.4 (12)
O2a—C4a—C9a—C8a179.9 (9)C4b—C5b—C6b—C7b0.00 (16)
O2a—C4a—C9a—C3a0.9 (17)C4b—C5b—C6b—O4b179.9 (9)
C5a—C4a—O2a—C12a5.6 (17)C5b—C6b—C7b—C8b0.00 (3)
C9a—C4a—O2a—C12a174.3 (13)C5b—C6b—C7b—Cl1b180.00 (4)
C4a—C5a—C6a—C7a0.1 (13)O4b—C6b—C7b—C8b180.00 (3)
C4a—C5a—C6a—O4a180.00 (5)O4b—C6b—C7b—Cl1b0.1 (11)
C5a—C6a—C7a—C8a0.00 (2)C5b—C6b—O4b—C13b6.9 (17)
C5a—C6a—C7a—Cl1a180.00 (4)C7b—C6b—O4b—C13b173.2 (12)
O4a—C6a—C7a—C8a180.00 (13)C6b—C7b—C8b—C9b0.1 (13)
O4a—C6a—C7a—Cl1a0.1 (11)C6b—C7b—C8b—O1b175.9 (9)
C5a—C6a—O4a—C13a2.9 (17)Cl1b—C7b—C8b—C9b180.00 (3)
C7a—C6a—O4a—C13a177.1 (12)Cl1b—C7b—C8b—O1b4.1 (13)
C6a—C7a—C8a—C9a0.00 (10)C7b—C8b—C9b—C4b0.00 (13)
C6a—C7a—C8a—O1a176.6 (9)C7b—C8b—C9b—C3b178.0 (10)
Cl1a—C7a—C8a—C9a180.00 (4)O1b—C8b—C9b—C4b176.3 (9)
Cl1a—C7a—C8a—O1a3.4 (13)O1b—C8b—C9b—C3b1.7 (13)
C7a—C8a—C9a—C4a0.00 (10)C7b—C8b—O1b—C2b172.7 (9)
C7a—C8a—C9a—C3a179.3 (10)C9b—C8b—O1b—C2b3.4 (13)
O1a—C8a—C9a—C4a176.9 (10)C4b—C9b—C3b—C2b172.2 (10)
O1a—C8a—C9a—C3a2.4 (13)C4b—C9b—C3b—O3b5 (3)
C7a—C8a—O1a—C2a178.6 (9)C8b—C9b—C3b—C2b5.6 (13)
C9a—C8a—O1a—C2a4.6 (13)C8b—C9b—C3b—O3b177.5 (16)
C4a—C9a—C3a—C2a180.0 (3)C9b—C3b—C2b—C6'b110.8 (11)
C4a—C9a—C3a—O3a1 (3)C9b—C3b—C2b—C2'b121.6 (11)
C8a—C9a—C3a—C2a0.8 (13)C9b—C3b—C2b—O1b7.5 (13)
C8a—C9a—C3a—O3a179.9 (16)O3b—C3b—C2b—C6'b66.3 (19)
C9a—C3a—C2a—C6'a120.3 (11)O3b—C3b—C2b—C2'b61.3 (19)
C9a—C3a—C2a—C2'a114.8 (12)O3b—C3b—C2b—O1b175.4 (15)
C9a—C3a—C2a—O1a3.3 (13)C3b—C2b—C6'b—C5'b84.2 (12)
O3a—C3a—C2a—C6'a60.4 (19)C3b—C2b—C6'b—C10b43.7 (14)
O3a—C3a—C2a—C2'a64.5 (19)C2'b—C2b—C6'b—C5'b40.5 (14)
O3a—C3a—C2a—O1a177.4 (15)C2'b—C2b—C6'b—C10b168.4 (11)
C3a—C2a—C6'a—C5'a84.4 (12)O1b—C2b—C6'b—C5'b159.3 (10)
C3a—C2a—C6'a—C10a46.7 (14)O1b—C2b—C6'b—C10b72.8 (13)
C2'a—C2a—C6'a—C5'a39.0 (14)C3b—C2b—C2'b—C4'b108.6 (9)
C2'a—C2a—C6'a—C10a170.1 (11)C3b—C2b—C2'b—C3'b105.3 (16)
O1a—C2a—C6'a—C5'a160.1 (10)C3b—C2b—C2'b—O6b68.4 (14)
O1a—C2a—C6'a—C10a68.8 (13)C6'b—C2b—C2'b—C4'b18.5 (11)
C3a—C2a—C2'a—C3'a116.9 (16)C6'b—C2b—C2'b—C3'b21.8 (19)
C3a—C2a—C2'a—O6a68.4 (15)C6'b—C2b—C2'b—O6b164.5 (11)
C3a—C2a—C2'a—C11a66 (2)O1b—C2b—C2'b—C4'b138.3 (9)
C6'a—C2a—C2'a—C3'a8 (2)O1b—C2b—C2'b—C3'b141.5 (15)
C6'a—C2a—C2'a—O6a166.7 (12)O1b—C2b—C2'b—O6b44.7 (15)
C6'a—C2a—C2'a—C11a169.0 (15)C3b—C2b—O1b—C8b6.7 (13)
O1a—C2a—C2'a—C3'a128.0 (16)C6'b—C2b—O1b—C8b114.7 (10)
O1a—C2a—C2'a—O6a46.8 (15)C2'b—C2b—O1b—C8b122.0 (10)
O1a—C2a—C2'a—C11a49 (2)C2b—C6'b—C5'b—C4'b45.5 (15)
C3a—C2a—O1a—C8a4.7 (13)C10b—C6'b—C5'b—C4'b174.5 (13)
C6'a—C2a—O1a—C8a124.6 (10)C6'b—C5'b—C4'b—C3'b31 (2)
C2'a—C2a—O1a—C8a113.0 (10)C6'b—C5'b—C4'b—C2'b26.0 (13)
C2a—C6'a—C5'a—C4'a48.9 (16)C6'b—C5'b—C4'b—O5b151.9 (17)
C10a—C6'a—C5'a—C4'a179.1 (13)C5'b—C4'b—C3'b—C2'b11 (2)
C6'a—C5'a—C4'a—C3'a28 (2)O5b—C4'b—C3'b—C2'b172.2 (18)
C6'a—C5'a—C4'a—O5a154.8 (17)C5'b—C4'b—C2'b—C2b4.4 (12)
C5'a—C4'a—C3'a—C2'a4 (3)C5'b—C4'b—C2'b—C3'b170 (2)
O5a—C4'a—C3'a—C2'a174.0 (19)C5'b—C4'b—C2'b—O6b169 (3)
C4'a—C3'a—C2'a—C2a14 (3)C3'b—C4'b—C2'b—C2b175 (2)
C4'a—C3'a—C2'a—O6a171.8 (17)C3'b—C4'b—C2'b—O6b1 (3)
C4'a—C3'a—C2'a—C11a167.7 (16)O5b—C4'b—C2'b—C2b172 (3)
C2a—C2'a—O6a—C11a177.2 (14)O5b—C4'b—C2'b—C3'b13 (3)
C3'a—C2'a—O6a—C11a8 (3)O5b—C4'b—C2'b—O6b15 (5)
C2a—C2'a—C11a—O6a4 (2)C4'b—C3'b—C2'b—C2b6 (2)
C3'a—C2'a—C11a—O6a173 (2)C4'b—C3'b—C2'b—O6b179.3 (15)
C9b—C4b—C5b—C6b0.1 (14)C2b—C2'b—O6b—C11b170.6 (12)
O2b—C4b—C5b—C6b179.9 (9)C4'b—C2'b—O6b—C11b2 (4)
C5b—C4b—C9b—C8b0.0000 (18)C3'b—C2'b—O6b—C11b3 (2)
C5b—C4b—C9b—C3b177.5 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13a—H36a···O5ai1.002.543.28 (3)130.00
C5a—H41a···O5ai1.002.493.459 (18)162.17
C11a—H28a···O3aii1.002.243.13 (2)147.00
C11a—H29a···O3biii1.002.343.34 (2)177.00
Symmetry codes: (i) x, y1, z; (ii) x1/2, y+1/2, z+2; (iii) x, y+1/2, z+3/2.
 

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