Absolute configuration of micromelin.

The title compound {systematic name: 7-meth-oxy-6-[(1R,2R,5R)-5-methyl-4-oxo-3,6-dioxabicyclo-[3.1.0]hexan-2-yl]-2H-chromen-2-one}, C(15)H(12)O(6), is a coumarin, which was isolated from the roots of Micromelum glanduliferum. There are two mol-ecules in the asymmetric unit with slight differences in bond angles. In both mol-ecules, the furan ring adopts a flattened envelope conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into chains along the a axis. Aromatic π-π stacking inter-actions with centroid-centroid distances in the range 3.6995 (11)-3.8069 (11) Å and C⋯O short contacts [3.030 (2)-3.171 (3) Å] also occur.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For background to plants in the Rutaceae family, coumarins and their activities, see: Ito et al. (1997 ▶, 2000 ▶); Kamperdick et al. (1999 ▶); Rahmani et al. (2003 ▶); Tangyuenyongwatthana et al. (1992 ▶); Tanti­shaiyakul et al. (1986 ▶); Tanti­vatana et al. (1983 ▶); Thuy et al. (1999 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C15H12O6

M = 288.25

Monoclinic,

a = 6.7514 (2) Å

b = 23.7537 (8) Å

c = 8.0730 (3) Å

β = 90.000 (1)°

V = 1294.67 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.98 mm−1

T = 100 K

0.56 × 0.22 × 0.19 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.609, T max = 0.838

21511 measured reflections

4392 independent reflections

4392 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.059

S = 1.06

4392 reflections

384 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Absolute structure: Flack (1983 ▶), 2632 Friedel pairs

Flack parameter: 0.06 (10)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022720/hb5904sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022720/hb5904Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022720/hb5904Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12O6	F(000) = 600
Mr = 288.25	Dx = 1.479 Mg m−3
Monoclinic, P21	Melting point = 491.0–492.2 (decompose) K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54178 Å
a = 6.7514 (2) Å	Cell parameters from 4392 reflections
b = 23.7537 (8) Å	θ = 1.9–67.5°
c = 8.0730 (3) Å	µ = 0.98 mm−1
β = 90.000 (1)°	T = 100 K
V = 1294.67 (8) Å3	Needle, colorless
Z = 4	0.56 × 0.22 × 0.19 mm

Bruker APEX DUO CCD diffractometer	4392 independent reflections
Radiation source: sealed tube	4392 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 67.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.609, Tmax = 0.838	k = −28→28
21511 measured reflections	l = −7→9

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)] = 0.022	H-atom parameters constrained
wR(F2) = 0.059
S = 1.06	(Δ/σ)max = 0.001
4392 reflections	Δρmax = 0.13 e Å−3
384 parameters	Δρmin = −0.13 e Å−3
1 restraint	Absolute structure: Flack (1983), 2632 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (10)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1A	0.5534 (2)	0.77310 (5)	0.20837 (17)	0.0204 (3)
O2A	0.5534 (2)	0.70240 (6)	0.03012 (18)	0.0264 (3)
O3A	0.74087 (18)	0.88672 (5)	0.89684 (16)	0.0216 (3)
O4A	0.8825 (2)	0.97077 (5)	0.92773 (18)	0.0269 (3)
O5A	0.4227 (2)	0.93361 (5)	1.05332 (16)	0.0241 (3)
O6A	0.5758 (2)	0.93052 (5)	0.57220 (16)	0.0241 (3)
C1A	0.5487 (3)	0.71597 (7)	0.1741 (2)	0.0202 (4)
C2A	0.5373 (2)	0.67836 (8)	0.3155 (3)	0.0214 (4)
H2A	0.5333	0.6397	0.2974	0.026*
C3A	0.5323 (3)	0.69786 (8)	0.4722 (2)	0.0201 (4)
H3A	0.5235	0.6727	0.5602	0.024*
C4A	0.5405 (3)	0.75717 (7)	0.5038 (2)	0.0181 (4)
C5A	0.5383 (3)	0.78164 (8)	0.6622 (3)	0.0181 (4)
H5A	0.5292	0.7584	0.7546	0.022*
C6A	0.5493 (3)	0.83936 (7)	0.6845 (2)	0.0195 (4)
C7A	0.5631 (3)	0.87404 (7)	0.5419 (2)	0.0189 (4)
C8A	0.5625 (3)	0.85146 (8)	0.3842 (3)	0.0195 (4)
H8A	0.5690	0.8746	0.2914	0.023*
C9A	0.5519 (3)	0.79334 (8)	0.3677 (2)	0.0182 (4)
C10A	0.4044 (3)	0.91242 (8)	0.8848 (2)	0.0211 (4)
H10A	0.2787	0.9151	0.8246	0.025*
C11A	0.5444 (3)	0.86343 (7)	0.8562 (2)	0.0215 (4)
H11A	0.5128	0.8333	0.9349	0.026*
C12A	0.7343 (3)	0.94293 (7)	0.9141 (2)	0.0212 (3)
C13A	0.5240 (3)	0.96269 (8)	0.9180 (2)	0.0225 (4)
C14A	0.4710 (3)	1.02263 (7)	0.8862 (2)	0.0281 (4)
H14A	0.3296	1.0268	0.8891	0.042*
H14B	0.5195	1.0337	0.7793	0.042*
H14C	0.5297	1.0460	0.9698	0.042*
C15A	0.5814 (3)	0.96784 (8)	0.4322 (2)	0.0272 (4)
H15A	0.5919	1.0060	0.4703	0.041*
H15B	0.4623	0.9635	0.3686	0.041*
H15C	0.6938	0.9589	0.3643	0.041*
O1B	0.05200 (18)	0.79463 (5)	0.46409 (16)	0.0183 (3)
O2B	0.0717 (2)	0.86476 (5)	0.64252 (16)	0.0242 (3)
O3B	0.23060 (19)	0.67681 (5)	−0.22314 (17)	0.0233 (3)
O4B	0.34079 (19)	0.58955 (6)	−0.2685 (2)	0.0318 (3)
O5B	−0.09923 (19)	0.64242 (5)	−0.38897 (15)	0.0236 (3)
O6B	0.04861 (19)	0.63788 (5)	0.09768 (17)	0.0225 (3)
C1B	0.0630 (3)	0.85163 (7)	0.4988 (2)	0.0203 (4)
C2B	0.0651 (3)	0.88964 (7)	0.3574 (2)	0.0199 (4)
H2B	0.0720	0.9282	0.3761	0.024*
C3B	0.0575 (3)	0.87071 (7)	0.2008 (2)	0.0197 (4)
H3B	0.0557	0.8961	0.1131	0.024*
C4B	0.0519 (3)	0.81105 (8)	0.1684 (2)	0.0178 (4)
C5B	0.0489 (3)	0.78703 (8)	0.0093 (2)	0.0199 (4)
H5B	0.0482	0.8104	−0.0831	0.024*
C6B	0.0471 (3)	0.72951 (8)	−0.0123 (2)	0.0194 (4)
C7B	0.0466 (3)	0.69415 (7)	0.1295 (2)	0.0192 (4)
C8B	0.0462 (3)	0.71642 (7)	0.2875 (3)	0.0175 (3)
H8B	0.0440	0.6931	0.3801	0.021*
C9B	0.0491 (3)	0.77488 (7)	0.3041 (2)	0.0179 (4)
C10B	−0.1127 (3)	0.66169 (7)	−0.2188 (3)	0.0215 (4)
H10B	−0.2398	0.6622	−0.1602	0.026*
C11B	0.0431 (3)	0.70558 (9)	−0.1849 (2)	0.0228 (4)
H11B	0.0254	0.7366	−0.2636	0.027*
C12B	0.2048 (3)	0.62152 (8)	−0.2490 (2)	0.0226 (4)
C13B	−0.0122 (3)	0.60858 (8)	−0.2562 (2)	0.0207 (4)
C14B	−0.0890 (3)	0.55004 (8)	−0.2368 (3)	0.0278 (4)
H14D	−0.2311	0.5507	−0.2342	0.042*
H14E	−0.0399	0.5343	−0.1353	0.042*
H14F	−0.0453	0.5275	−0.3284	0.042*
C15B	0.0417 (3)	0.60079 (7)	0.2381 (2)	0.0223 (4)
H15D	0.0417	0.5624	0.2007	0.033*
H15E	−0.0765	0.6079	0.3007	0.033*
H15F	0.1555	0.6072	0.3069	0.033*

	U11	U22	U33	U12	U13	U23
O1A	0.0222 (6)	0.0233 (7)	0.0158 (7)	0.0021 (5)	−0.0004 (5)	−0.0002 (5)
O2A	0.0267 (7)	0.0324 (7)	0.0201 (8)	0.0025 (6)	−0.0010 (6)	−0.0059 (6)
O3A	0.0261 (6)	0.0169 (5)	0.0217 (7)	−0.0002 (5)	−0.0085 (6)	−0.0002 (5)
O4A	0.0280 (7)	0.0249 (6)	0.0278 (8)	−0.0054 (5)	−0.0071 (6)	−0.0003 (5)
O5A	0.0309 (7)	0.0241 (6)	0.0171 (6)	−0.0045 (5)	0.0002 (5)	−0.0034 (5)
O6A	0.0348 (7)	0.0188 (6)	0.0188 (7)	−0.0023 (5)	−0.0023 (6)	0.0039 (5)
C1A	0.0148 (8)	0.0238 (9)	0.0219 (11)	0.0021 (7)	−0.0029 (7)	−0.0024 (7)
C2A	0.0169 (8)	0.0224 (8)	0.0248 (10)	−0.0003 (7)	−0.0031 (7)	−0.0036 (7)
C3A	0.0148 (8)	0.0233 (9)	0.0223 (11)	−0.0016 (7)	−0.0022 (7)	0.0022 (7)
C4A	0.0138 (8)	0.0209 (9)	0.0197 (9)	−0.0004 (6)	−0.0014 (7)	0.0021 (7)
C5A	0.0149 (8)	0.0194 (8)	0.0201 (9)	−0.0013 (6)	−0.0030 (7)	0.0050 (6)
C6A	0.0174 (8)	0.0210 (9)	0.0202 (10)	−0.0014 (7)	−0.0064 (7)	0.0011 (7)
C7A	0.0172 (8)	0.0193 (9)	0.0202 (10)	−0.0008 (7)	−0.0029 (7)	0.0035 (7)
C8A	0.0173 (8)	0.0232 (9)	0.0179 (9)	0.0001 (7)	−0.0019 (7)	0.0045 (7)
C9A	0.0126 (8)	0.0243 (9)	0.0178 (10)	0.0007 (7)	−0.0013 (8)	0.0004 (7)
C10A	0.0265 (8)	0.0225 (8)	0.0142 (9)	−0.0010 (8)	−0.0023 (7)	−0.0007 (7)
C11A	0.0248 (8)	0.0204 (9)	0.0193 (10)	−0.0049 (7)	−0.0051 (8)	0.0039 (7)
C12A	0.0297 (9)	0.0212 (8)	0.0127 (9)	−0.0039 (7)	−0.0063 (7)	0.0037 (6)
C13A	0.0298 (9)	0.0233 (8)	0.0143 (9)	−0.0020 (8)	−0.0036 (7)	0.0011 (7)
C14A	0.0325 (10)	0.0261 (10)	0.0258 (10)	0.0044 (8)	0.0000 (8)	−0.0006 (7)
C15A	0.0388 (11)	0.0206 (8)	0.0222 (10)	−0.0016 (8)	0.0005 (8)	0.0067 (7)
O1B	0.0193 (6)	0.0204 (6)	0.0153 (7)	0.0001 (5)	−0.0028 (5)	−0.0005 (5)
O2B	0.0288 (7)	0.0248 (7)	0.0192 (7)	−0.0029 (6)	−0.0037 (5)	−0.0047 (5)
O3B	0.0241 (6)	0.0253 (6)	0.0205 (7)	−0.0007 (5)	0.0035 (5)	−0.0015 (5)
O4B	0.0288 (7)	0.0317 (7)	0.0349 (8)	0.0085 (6)	0.0011 (6)	−0.0057 (6)
O5B	0.0318 (7)	0.0250 (6)	0.0139 (6)	0.0045 (5)	−0.0027 (5)	−0.0007 (5)
O6B	0.0306 (7)	0.0187 (6)	0.0181 (7)	0.0036 (5)	−0.0002 (6)	0.0005 (5)
C1B	0.0145 (8)	0.0204 (8)	0.0261 (12)	−0.0001 (7)	−0.0020 (7)	−0.0038 (7)
C2B	0.0171 (8)	0.0168 (8)	0.0259 (10)	−0.0012 (7)	−0.0040 (7)	−0.0007 (7)
C3B	0.0154 (8)	0.0204 (8)	0.0232 (10)	−0.0007 (7)	−0.0019 (8)	0.0027 (7)
C4B	0.0141 (8)	0.0191 (9)	0.0202 (10)	0.0007 (6)	−0.0027 (7)	0.0029 (7)
C5B	0.0186 (8)	0.0239 (9)	0.0172 (9)	0.0020 (7)	−0.0001 (7)	0.0037 (7)
C6B	0.0184 (8)	0.0212 (9)	0.0185 (10)	0.0031 (7)	−0.0023 (8)	0.0003 (7)
C7B	0.0166 (8)	0.0178 (8)	0.0231 (10)	0.0028 (7)	−0.0018 (7)	−0.0016 (7)
C8B	0.0163 (7)	0.0177 (8)	0.0184 (9)	0.0028 (6)	−0.0018 (7)	0.0054 (6)
C9B	0.0157 (8)	0.0221 (9)	0.0161 (9)	0.0005 (7)	−0.0021 (7)	−0.0026 (7)
C10B	0.0253 (9)	0.0258 (9)	0.0133 (9)	0.0044 (7)	−0.0019 (7)	−0.0013 (6)
C11B	0.0284 (9)	0.0226 (9)	0.0173 (10)	0.0050 (8)	0.0007 (8)	0.0007 (7)
C12B	0.0295 (9)	0.0239 (9)	0.0145 (10)	0.0013 (7)	0.0005 (7)	0.0008 (7)
C13B	0.0255 (8)	0.0238 (9)	0.0127 (10)	0.0033 (7)	−0.0010 (7)	0.0009 (7)
C14B	0.0339 (10)	0.0252 (9)	0.0243 (10)	−0.0033 (8)	−0.0034 (9)	−0.0007 (7)
C15B	0.0284 (8)	0.0188 (8)	0.0197 (9)	0.0032 (7)	−0.0017 (8)	0.0021 (7)

O1A—C9A	1.373 (2)	O1B—C9B	1.374 (2)
O1A—C1A	1.385 (2)	O1B—C1B	1.385 (2)
O2A—C1A	1.207 (2)	O2B—C1B	1.203 (2)
O3A—C12A	1.343 (2)	O3B—C12B	1.341 (2)
O3A—C11A	1.474 (2)	O3B—C11B	1.471 (2)
O4A—C12A	1.204 (2)	O4B—C12B	1.202 (2)
O5A—C10A	1.456 (2)	O5B—C10B	1.451 (2)
O5A—C13A	1.462 (2)	O5B—C13B	1.463 (2)
O6A—C7A	1.366 (2)	O6B—C7B	1.361 (2)
O6A—C15A	1.437 (2)	O6B—C15B	1.437 (2)
C1A—C2A	1.451 (3)	C1B—C2B	1.455 (3)
C2A—C3A	1.348 (3)	C2B—C3B	1.343 (3)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.433 (2)	C3B—C4B	1.441 (2)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C9A	1.397 (3)	C4B—C9B	1.392 (2)
C4A—C5A	1.405 (3)	C4B—C5B	1.406 (3)
C5A—C6A	1.385 (2)	C5B—C6B	1.377 (3)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.419 (2)	C6B—C7B	1.420 (3)
C6A—C11A	1.500 (3)	C6B—C11B	1.505 (3)
C7A—C8A	1.381 (3)	C7B—C8B	1.381 (3)
C8A—C9A	1.389 (3)	C8B—C9B	1.395 (2)
C8A—H8A	0.9300	C8B—H8B	0.9300
C10A—C13A	1.466 (3)	C10B—C13B	1.464 (3)
C10A—C11A	1.517 (3)	C10B—C11B	1.506 (3)
C10A—H10A	0.9800	C10B—H10B	0.9800
C11A—H11A	0.9800	C11B—H11B	0.9800
C12A—C13A	1.496 (3)	C12B—C13B	1.498 (2)
C13A—C14A	1.490 (2)	C13B—C14B	1.492 (2)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C9A—O1A—C1A	121.99 (14)	C9B—O1B—C1B	121.63 (13)
C12A—O3A—C11A	111.50 (14)	C12B—O3B—C11B	112.06 (15)
C10A—O5A—C13A	60.32 (11)	C10B—O5B—C13B	60.31 (11)
C7A—O6A—C15A	117.82 (14)	C7B—O6B—C15B	116.94 (15)
O2A—C1A—O1A	116.95 (16)	O2B—C1B—O1B	116.82 (16)
O2A—C1A—C2A	126.46 (16)	O2B—C1B—C2B	126.52 (16)
O1A—C1A—C2A	116.58 (16)	O1B—C1B—C2B	116.66 (16)
C3A—C2A—C1A	121.86 (17)	C3B—C2B—C1B	122.02 (16)
C3A—C2A—H2A	119.1	C3B—C2B—H2B	119.0
C1A—C2A—H2A	119.1	C1B—C2B—H2B	119.0
C2A—C3A—C4A	120.27 (17)	C2B—C3B—C4B	120.06 (16)
C2A—C3A—H3A	119.9	C2B—C3B—H3B	120.0
C4A—C3A—H3A	119.9	C4B—C3B—H3B	120.0
C9A—C4A—C5A	117.51 (16)	C9B—C4B—C5B	117.92 (16)
C9A—C4A—C3A	117.85 (18)	C9B—C4B—C3B	117.67 (17)
C5A—C4A—C3A	124.65 (16)	C5B—C4B—C3B	124.41 (16)
C6A—C5A—C4A	121.84 (18)	C6B—C5B—C4B	121.22 (17)
C6A—C5A—H5A	119.1	C6B—C5B—H5B	119.4
C4A—C5A—H5A	119.1	C4B—C5B—H5B	119.4
C5A—C6A—C7A	118.23 (17)	C5B—C6B—C7B	119.00 (17)
C5A—C6A—C11A	119.76 (17)	C5B—C6B—C11B	119.47 (17)
C7A—C6A—C11A	122.01 (15)	C7B—C6B—C11B	121.53 (16)
O6A—C7A—C8A	123.13 (16)	O6B—C7B—C8B	123.40 (16)
O6A—C7A—C6A	115.41 (15)	O6B—C7B—C6B	115.39 (16)
C8A—C7A—C6A	121.47 (16)	C8B—C7B—C6B	121.20 (16)
C7A—C8A—C9A	118.33 (16)	C7B—C8B—C9B	118.02 (16)
C7A—C8A—H8A	120.8	C7B—C8B—H8B	121.0
C9A—C8A—H8A	120.8	C9B—C8B—H8B	121.0
O1A—C9A—C8A	115.95 (15)	O1B—C9B—C4B	121.91 (16)
O1A—C9A—C4A	121.44 (16)	O1B—C9B—C8B	115.46 (15)
C8A—C9A—C4A	122.62 (17)	C4B—C9B—C8B	122.62 (17)
O5A—C10A—C13A	60.06 (12)	O5B—C10B—C13B	60.26 (12)
O5A—C10A—C11A	110.76 (14)	O5B—C10B—C11B	110.29 (15)
C13A—C10A—C11A	108.03 (15)	C13B—C10B—C11B	108.09 (15)
O5A—C10A—H10A	120.9	O5B—C10B—H10B	121.0
C13A—C10A—H10A	120.9	C13B—C10B—H10B	121.0
C11A—C10A—H10A	120.9	C11B—C10B—H10B	121.0
O3A—C11A—C6A	109.19 (15)	O3B—C11B—C6B	110.73 (15)
O3A—C11A—C10A	103.82 (14)	O3B—C11B—C10B	103.96 (15)
C6A—C11A—C10A	116.54 (15)	C6B—C11B—C10B	116.25 (17)
O3A—C11A—H11A	109.0	O3B—C11B—H11B	108.5
C6A—C11A—H11A	109.0	C6B—C11B—H11B	108.5
C10A—C11A—H11A	109.0	C10B—C11B—H11B	108.5
O4A—C12A—O3A	121.87 (16)	O4B—C12B—O3B	122.68 (18)
O4A—C12A—C13A	127.90 (16)	O4B—C12B—C13B	127.76 (17)
O3A—C12A—C13A	110.21 (15)	O3B—C12B—C13B	109.51 (16)
O5A—C13A—C10A	59.62 (11)	O5B—C13B—C10B	59.43 (11)
O5A—C13A—C14A	117.86 (16)	O5B—C13B—C14B	116.71 (15)
C10A—C13A—C14A	127.90 (17)	C10B—C13B—C14B	128.36 (16)
O5A—C13A—C12A	108.14 (14)	O5B—C13B—C12B	107.97 (15)
C10A—C13A—C12A	105.27 (15)	C10B—C13B—C12B	105.57 (15)
C14A—C13A—C12A	121.63 (16)	C14B—C13B—C12B	121.78 (15)
C13A—C14A—H14A	109.5	C13B—C14B—H14D	109.5
C13A—C14A—H14B	109.5	C13B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C13A—C14A—H14C	109.5	C13B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
O6A—C15A—H15A	109.5	O6B—C15B—H15D	109.5
O6A—C15A—H15B	109.5	O6B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O6A—C15A—H15C	109.5	O6B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C9A—O1A—C1A—O2A	−178.97 (17)	C9B—O1B—C1B—O2B	−177.49 (14)
C9A—O1A—C1A—C2A	1.4 (3)	C9B—O1B—C1B—C2B	1.9 (2)
O2A—C1A—C2A—C3A	−179.84 (19)	O2B—C1B—C2B—C3B	179.08 (18)
O1A—C1A—C2A—C3A	−0.3 (3)	O1B—C1B—C2B—C3B	−0.2 (2)
C1A—C2A—C3A—C4A	−0.7 (3)	C1B—C2B—C3B—C4B	−1.6 (3)
C2A—C3A—C4A—C9A	0.6 (3)	C2B—C3B—C4B—C9B	1.8 (3)
C2A—C3A—C4A—C5A	−179.32 (16)	C2B—C3B—C4B—C5B	−178.27 (16)
C9A—C4A—C5A—C6A	−0.8 (3)	C9B—C4B—C5B—C6B	−1.2 (3)
C3A—C4A—C5A—C6A	179.12 (16)	C3B—C4B—C5B—C6B	178.86 (17)
C4A—C5A—C6A—C7A	0.0 (3)	C4B—C5B—C6B—C7B	0.5 (3)
C4A—C5A—C6A—C11A	179.40 (16)	C4B—C5B—C6B—C11B	179.74 (17)
C15A—O6A—C7A—C8A	2.3 (3)	C15B—O6B—C7B—C8B	2.6 (3)
C15A—O6A—C7A—C6A	−177.34 (16)	C15B—O6B—C7B—C6B	−178.06 (14)
C5A—C6A—C7A—O6A	−179.27 (15)	C5B—C6B—C7B—O6B	−178.79 (15)
C11A—C6A—C7A—O6A	1.3 (3)	C11B—C6B—C7B—O6B	2.0 (3)
C5A—C6A—C7A—C8A	1.1 (3)	C5B—C6B—C7B—C8B	0.6 (3)
C11A—C6A—C7A—C8A	−178.34 (17)	C11B—C6B—C7B—C8B	−178.65 (17)
O6A—C7A—C8A—C9A	179.09 (16)	O6B—C7B—C8B—C9B	178.41 (14)
C6A—C7A—C8A—C9A	−1.3 (3)	C6B—C7B—C8B—C9B	−0.9 (3)
C1A—O1A—C9A—C8A	178.32 (14)	C1B—O1B—C9B—C4B	−1.7 (3)
C1A—O1A—C9A—C4A	−1.6 (3)	C1B—O1B—C9B—C8B	177.39 (14)
C7A—C8A—C9A—O1A	−179.47 (16)	C5B—C4B—C9B—O1B	179.89 (14)
C7A—C8A—C9A—C4A	0.4 (3)	C3B—C4B—C9B—O1B	−0.1 (3)
C5A—C4A—C9A—O1A	−179.54 (16)	C5B—C4B—C9B—C8B	0.8 (3)
C3A—C4A—C9A—O1A	0.6 (3)	C3B—C4B—C9B—C8B	−179.19 (14)
C5A—C4A—C9A—C8A	0.6 (3)	C7B—C8B—C9B—O1B	−178.93 (14)
C3A—C4A—C9A—C8A	−179.34 (16)	C7B—C8B—C9B—C4B	0.2 (3)
C13A—O5A—C10A—C11A	99.42 (16)	C13B—O5B—C10B—C11B	99.79 (16)
C12A—O3A—C11A—C6A	113.83 (16)	C12B—O3B—C11B—C6B	116.25 (18)
C12A—O3A—C11A—C10A	−11.11 (18)	C12B—O3B—C11B—C10B	−9.3 (2)
C5A—C6A—C11A—O3A	110.37 (17)	C5B—C6B—C11B—O3B	112.02 (18)
C7A—C6A—C11A—O3A	−70.2 (2)	C7B—C6B—C11B—O3B	−68.8 (2)
C5A—C6A—C11A—C10A	−132.47 (18)	C5B—C6B—C11B—C10B	−129.66 (19)
C7A—C6A—C11A—C10A	46.9 (2)	C7B—C6B—C11B—C10B	49.6 (2)
O5A—C10A—C11A—O3A	−56.68 (17)	O5B—C10B—C11B—O3B	−57.98 (18)
C13A—C10A—C11A—O3A	7.34 (19)	C13B—C10B—C11B—O3B	6.2 (2)
O5A—C10A—C11A—C6A	−176.76 (14)	O5B—C10B—C11B—C6B	−179.94 (14)
C13A—C10A—C11A—C6A	−112.74 (17)	C13B—C10B—C11B—C6B	−115.77 (19)
C11A—O3A—C12A—O4A	−170.99 (17)	C11B—O3B—C12B—O4B	−173.74 (18)
C11A—O3A—C12A—C13A	10.6 (2)	C11B—O3B—C12B—C13B	8.7 (2)
C10A—O5A—C13A—C14A	119.70 (18)	C10B—O5B—C13B—C14B	120.65 (18)
C10A—O5A—C13A—C12A	−97.43 (17)	C10B—O5B—C13B—C12B	−97.83 (16)
C11A—C10A—C13A—O5A	−104.05 (15)	C11B—C10B—C13B—O5B	−103.51 (16)
O5A—C10A—C13A—C14A	−103.3 (2)	O5B—C10B—C13B—C14B	−101.4 (2)
C11A—C10A—C13A—C14A	152.64 (19)	C11B—C10B—C13B—C14B	155.06 (19)
O5A—C10A—C13A—C12A	102.35 (16)	O5B—C10B—C13B—C12B	101.97 (16)
C11A—C10A—C13A—C12A	−1.7 (2)	C11B—C10B—C13B—C12B	−1.5 (2)
O4A—C12A—C13A—O5A	−121.19 (19)	O4B—C12B—C13B—O5B	−119.4 (2)
O3A—C12A—C13A—O5A	57.12 (19)	O3B—C12B—C13B—O5B	58.02 (19)
O4A—C12A—C13A—C10A	176.34 (19)	O4B—C12B—C13B—C10B	178.3 (2)
O3A—C12A—C13A—C10A	−5.3 (2)	O3B—C12B—C13B—C10B	−4.3 (2)
O4A—C12A—C13A—C14A	20.0 (3)	O4B—C12B—C13B—C14B	19.8 (3)
O3A—C12A—C13A—C14A	−161.68 (15)	O3B—C12B—C13B—C14B	−162.80 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3B—H3B···O4Ai	0.93	2.60	3.450 (2)	152
C5A—H5A···O2Aii	0.93	2.60	3.518 (3)	171
C5B—H5B···O2Biii	0.93	2.57	3.493 (2)	173
C8A—H8A···O5Aiii	0.93	2.58	3.440 (3)	155
C8B—H8B···O5Bii	0.93	2.42	3.298 (3)	157
C10A—H10A···O2B	0.98	2.35	3.186 (2)	142
C10B—H10B···O2Aiv	0.98	2.29	3.171 (3)	150
C14B—H14E···O4Av	0.96	2.49	3.423 (3)	163
C15B—H15D···O4Av	0.96	2.46	3.405 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3B—H3B⋯O4Ai	0.93	2.60	3.450 (2)	152
C5A—H5A⋯O2Aii	0.93	2.60	3.518 (3)	171
C5B—H5B⋯O2Biii	0.93	2.57	3.493 (2)	173
C8A—H8A⋯O5Aiii	0.93	2.58	3.440 (3)	155
C8B—H8B⋯O5Bii	0.93	2.42	3.298 (3)	157
C10A—H10A⋯O2B	0.98	2.35	3.186 (2)	142
C10B—H10B⋯O2Aiv	0.98	2.29	3.171 (3)	150
C14B—H14E⋯O4Av	0.96	2.49	3.423 (3)	163
C15B—H15D⋯O4Av	0.96	2.46	3.405 (2)	166

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .