3,6,9-Trimethyl-2,3-dihydro­benzo[de]chromene-7,8-dione

Fun, H.-K.; Boonsri, S.; Chantrapromma, S.; Boonnak, N.; Karalai, C.

doi:10.1107/S1600536807014547

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3,6,9-Trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione

H.-K. Fun, S. Boonsri, S. Chantrapromma, N. Boonnak and C. Karalai

The title sesquiterpene ortho-naphthoquinone compound, C₁₅H₁₄O₃, was isolated from Thespesia populnea. There are four independent molecules (A, B, C and D) in the asymmetric unit. The conformations of molecules A and B differ from those observed for C and D. In all four molecules, the pyran ring adopts an envelope conformation, with the methylene C atom as the flap atom. The molecules are arranged in layers parallel to the (100) plane, and are interconnected into a three-dimensional network by C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014547/ci2328sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014547/ci2328Isup2.hkl Contains datablock I

CCDC reference: 648062

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R factor = 0.061
wR factor = 0.166
Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C1A    -C6A           1.46 Ang.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C1C    -C6C           1.46 Ang.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C1D    -C6D           1.45 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C1A    -C6A           0.19 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C1B    -C6B           0.19 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C1C    -C6C           0.18 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C1D    -C6D           0.20 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C4A    -   C5A    ...       1.56 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C4B    -   C5B    ...       1.55 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C4C    -   C5C    ...       1.54 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C4D    -   C5D    ...       1.55 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety       C14D
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

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           30.00
           From the CIF: _reflns_number_total               7133
           Count of symmetry unique reflns         7136
           Completeness (_total/calc)             99.96%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11A   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11B   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11C   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11D   = .          R

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3,6,9-trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione top

Crystal data top

C₁₅H₁₄O₃	F(000) = 1024
M_r = 242.26	D_x = 1.350 Mg m⁻³
Monoclinic, P2₁	Melting point = 381–383 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 7.1615 (1) Å	Cell parameters from 7133 reflections
b = 18.6558 (3) Å	θ = 1.1–30.0°
c = 18.0323 (3) Å	µ = 0.09 mm⁻¹
β = 98.216 (1)°	T = 100 K
V = 2384.45 (6) Å³	Block, orange
Z = 8	0.32 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	7133 independent reflections
Radiation source: fine-focus sealed tube	4478 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.1°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −23→26
T_min = 0.971, T_max = 0.991	l = −25→24
30798 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0867P)²] where P = (F_o² + 2F_c²)/3
7133 reflections	(Δ/σ)_max = 0.001
661 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1A	0.6580 (4)	0.21187 (14)	0.70449 (15)	0.0282 (6)
O2A	0.5580 (5)	0.05077 (16)	0.50539 (17)	0.0397 (8)
O3A	0.5400 (5)	0.15793 (17)	0.40699 (16)	0.0369 (7)
C1A	0.5790 (5)	0.2599 (2)	0.5788 (2)	0.0206 (8)
C2A	0.6183 (5)	0.1992 (2)	0.6299 (2)	0.0220 (8)
C3A	0.6100 (6)	0.1286 (2)	0.6089 (2)	0.0259 (9)
C4A	0.5695 (6)	0.1118 (2)	0.5300 (2)	0.0290 (9)
C5A	0.5494 (6)	0.1743 (2)	0.4720 (2)	0.0258 (9)
C6A	0.5450 (5)	0.2486 (2)	0.5000 (2)	0.0210 (8)
C7A	0.5062 (6)	0.3073 (2)	0.4513 (2)	0.0268 (9)
C8A	0.4989 (6)	0.3753 (2)	0.4825 (2)	0.0288 (9)
H8AA	0.4713	0.4144	0.4509	0.035*
C9A	0.5309 (6)	0.3867 (2)	0.5586 (2)	0.0287 (9)
H9AA	0.5256	0.4329	0.5774	0.034*
C10A	0.5715 (5)	0.3286 (2)	0.6081 (2)	0.0228 (8)
C11A	0.6075 (6)	0.3408 (2)	0.6920 (2)	0.0250 (8)
H11A	0.6750	0.3864	0.7013	0.030*
C12A	0.7348 (6)	0.2819 (2)	0.7266 (2)	0.0296 (9)
H12A	0.8582	0.2869	0.7109	0.036*
H12B	0.7500	0.2860	0.7807	0.036*
C13A	0.6482 (7)	0.0684 (2)	0.6645 (2)	0.0349 (10)
H13A	0.7416	0.0833	0.7052	0.052*
H13B	0.6937	0.0274	0.6403	0.052*
H13C	0.5338	0.0561	0.6835	0.052*
C14A	0.4724 (7)	0.2999 (3)	0.3673 (2)	0.0344 (10)
H14A	0.4366	0.3455	0.3450	0.052*
H14B	0.3731	0.2658	0.3532	0.052*
H14C	0.5858	0.2836	0.3500	0.052*
C15A	0.4225 (6)	0.3460 (2)	0.7260 (2)	0.0299 (9)
H15A	0.4507	0.3567	0.7785	0.045*
H15B	0.3563	0.3012	0.7193	0.045*
H15C	0.3452	0.3835	0.7013	0.045*
O1B	0.0281 (6)	−0.00811 (17)	0.47135 (18)	0.0447 (9)
O2B	0.1842 (5)	0.08673 (19)	0.71010 (17)	0.0439 (8)
O3B	0.0985 (4)	0.21937 (17)	0.65883 (17)	0.0362 (7)
C1B	0.0381 (6)	0.1206 (2)	0.4840 (2)	0.0258 (9)
C2B	0.0554 (6)	0.0488 (2)	0.5175 (2)	0.0309 (10)
C3B	0.1082 (7)	0.0355 (2)	0.5917 (2)	0.0344 (10)
C4B	0.1359 (6)	0.0942 (2)	0.6426 (2)	0.0310 (9)
C5B	0.0954 (6)	0.1717 (2)	0.6135 (2)	0.0270 (9)
C6B	0.0550 (6)	0.1828 (2)	0.5303 (2)	0.0281 (9)
C7B	0.0395 (6)	0.2515 (2)	0.4986 (2)	0.0271 (9)
C8B	0.0118 (6)	0.2565 (2)	0.4203 (3)	0.0327 (10)
H8BA	0.0028	0.3014	0.3978	0.039*
C9B	−0.0024 (6)	0.1962 (2)	0.3762 (2)	0.0290 (9)
H9BA	−0.0181	0.2016	0.3244	0.035*
C10B	0.0056 (6)	0.1278 (2)	0.4060 (2)	0.0269 (9)
C11B	−0.0124 (7)	0.0629 (2)	0.3567 (2)	0.0331 (10)
H11B	−0.1054	0.0734	0.3127	0.040*
C12B	−0.0878 (8)	0.0028 (3)	0.3993 (3)	0.0422 (12)
H12C	−0.2159	0.0139	0.4071	0.051*
H12D	−0.0908	−0.0409	0.3702	0.051*
C13B	0.1301 (9)	−0.0389 (3)	0.6226 (3)	0.0489 (14)
H13D	0.1818	−0.0693	0.5876	0.073*
H13E	0.0092	−0.0570	0.6306	0.073*
H13F	0.2136	−0.0382	0.6692	0.073*
C14B	0.0538 (7)	0.3195 (2)	0.5433 (3)	0.0350 (11)
H14D	0.1694	0.3195	0.5777	0.052*
H14E	−0.0512	0.3228	0.5708	0.052*
H14F	0.0525	0.3598	0.5101	0.052*
C15B	0.1747 (7)	0.0454 (2)	0.3298 (2)	0.0365 (11)
H15D	0.2093	0.0840	0.2992	0.055*
H15E	0.1620	0.0020	0.3010	0.055*
H15F	0.2707	0.0393	0.3723	0.055*
O1C	0.4970 (4)	0.23221 (15)	1.19470 (15)	0.0305 (7)
O2C	0.5707 (5)	0.40133 (17)	1.01213 (18)	0.0384 (8)
O3C	0.6244 (4)	0.29885 (18)	0.91400 (17)	0.0352 (7)
C1C	0.5238 (5)	0.1891 (2)	1.0696 (2)	0.0200 (8)
C2C	0.5218 (6)	0.2485 (2)	1.1238 (2)	0.0253 (8)
C3C	0.5330 (6)	0.3195 (2)	1.1074 (2)	0.0292 (9)
C4C	0.5597 (6)	0.3387 (2)	1.0318 (2)	0.0289 (9)
C5C	0.5808 (6)	0.2800 (2)	0.9737 (2)	0.0264 (9)
C6C	0.5520 (6)	0.2039 (2)	0.9942 (2)	0.0235 (8)
C7C	0.5458 (6)	0.1485 (2)	0.9417 (2)	0.0281 (9)
C8C	0.5140 (6)	0.0791 (2)	0.9657 (2)	0.0291 (9)
H8CA	0.5122	0.0415	0.9318	0.035*
C9C	0.4853 (6)	0.0645 (2)	1.0381 (2)	0.0278 (9)
H9CA	0.4622	0.0176	1.0516	0.033*
C10C	0.4904 (5)	0.1192 (2)	1.0918 (2)	0.0232 (8)
C11C	0.4568 (6)	0.1035 (2)	1.1708 (2)	0.0263 (9)
H11C	0.3210	0.1059	1.1728	0.032*
C12C	0.5541 (6)	0.1611 (2)	1.2211 (2)	0.0303 (9)
H12E	0.5240	0.1547	1.2715	0.036*
H12F	0.6896	0.1564	1.2231	0.036*
C13C	0.5224 (7)	0.3783 (2)	1.1636 (3)	0.0379 (11)
H13G	0.5332	0.3581	1.2130	0.057*
H13H	0.4037	0.4027	1.1524	0.057*
H13I	0.6234	0.4117	1.1613	0.057*
C14C	0.5694 (6)	0.1594 (3)	0.8602 (2)	0.0320 (10)
H14G	0.5439	0.1153	0.8333	0.048*
H14H	0.6964	0.1744	0.8571	0.048*
H14I	0.4830	0.1956	0.8385	0.048*
C15C	0.5297 (7)	0.0300 (2)	1.2000 (2)	0.0327 (10)
H15G	0.5087	0.0245	1.2511	0.049*
H15H	0.6623	0.0265	1.1974	0.049*
H15I	0.4637	−0.0071	1.1700	0.049*
O1D	1.0754 (5)	0.37834 (17)	1.05163 (17)	0.0385 (8)
O2D	0.9971 (4)	0.16851 (17)	1.18210 (17)	0.0344 (7)
O3D	0.9832 (4)	0.08972 (17)	1.05741 (17)	0.0362 (7)
C1D	1.0648 (5)	0.2665 (2)	0.9836 (2)	0.0225 (8)
C2D	1.0529 (6)	0.3061 (2)	1.0529 (2)	0.0289 (9)
C3D	1.0312 (6)	0.2760 (2)	1.1192 (2)	0.0299 (9)
C4D	1.0137 (6)	0.1999 (2)	1.1236 (2)	0.0293 (9)
C5D	1.0099 (5)	0.1535 (2)	1.0520 (2)	0.0267 (9)
C6D	1.0425 (5)	0.1904 (2)	0.9816 (2)	0.0255 (9)
C7D	1.0586 (5)	0.1517 (2)	0.9159 (2)	0.0264 (9)
C8D	1.1000 (6)	0.1899 (2)	0.8539 (2)	0.0283 (9)
H8DA	1.1119	0.1652	0.8100	0.034*
C9D	1.1241 (5)	0.2637 (2)	0.8556 (2)	0.0269 (9)
H9DA	1.1552	0.2872	0.8135	0.032*
C10D	1.1024 (6)	0.3034 (2)	0.9195 (2)	0.0253 (9)
C11D	1.1177 (6)	0.3842 (2)	0.9189 (2)	0.0292 (9)
H11D	1.2514	0.3974	0.9287	0.035*
C12D	1.0205 (7)	0.4143 (2)	0.9807 (2)	0.0362 (11)
H12G	1.0501	0.4649	0.9866	0.043*
H12H	0.8851	0.4099	0.9667	0.043*
C13D	1.0272 (8)	0.3190 (3)	1.1908 (3)	0.0398 (11)
H13J	1.0288	0.3693	1.1795	0.060*
H13K	1.1358	0.3072	1.2263	0.060*
H13L	0.9147	0.3077	1.2116	0.060*
C14D	1.0288 (6)	0.0721 (2)	0.9077 (3)	0.0317 (10)
H14J	1.0474	0.0576	0.8582	0.048*
H14K	0.9026	0.0604	0.9157	0.048*
H14L	1.1173	0.0475	0.9440	0.048*
C15D	1.0303 (7)	0.4193 (2)	0.8452 (2)	0.0329 (10)
H15J	1.0345	0.4705	0.8506	0.049*
H15K	0.9015	0.4040	0.8329	0.049*
H15L	1.1000	0.4053	0.8059	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0432 (17)	0.0232 (15)	0.0188 (14)	0.0001 (13)	0.0057 (12)	−0.0015 (11)
O2A	0.067 (2)	0.0238 (17)	0.0289 (17)	−0.0033 (16)	0.0087 (16)	−0.0068 (13)
O3A	0.054 (2)	0.0357 (18)	0.0208 (15)	−0.0065 (16)	0.0052 (14)	−0.0057 (14)
C1A	0.0208 (18)	0.0224 (19)	0.0186 (18)	−0.0016 (16)	0.0030 (15)	0.0022 (15)
C2A	0.0267 (19)	0.025 (2)	0.0156 (17)	0.0025 (17)	0.0062 (15)	0.0032 (15)
C3A	0.030 (2)	0.023 (2)	0.027 (2)	0.0040 (17)	0.0085 (17)	0.0042 (17)
C4A	0.039 (2)	0.023 (2)	0.027 (2)	−0.0039 (18)	0.0121 (18)	−0.0056 (17)
C5A	0.029 (2)	0.026 (2)	0.023 (2)	−0.0027 (17)	0.0049 (16)	−0.0006 (16)
C6A	0.0235 (19)	0.0230 (19)	0.0170 (17)	−0.0015 (16)	0.0047 (15)	0.0006 (15)
C7A	0.028 (2)	0.028 (2)	0.025 (2)	0.0008 (18)	0.0066 (17)	0.0029 (18)
C8A	0.034 (2)	0.027 (2)	0.025 (2)	0.0002 (18)	0.0045 (18)	0.0079 (17)
C9A	0.033 (2)	0.022 (2)	0.031 (2)	0.0010 (18)	0.0036 (18)	0.0031 (17)
C10A	0.0230 (19)	0.026 (2)	0.0197 (19)	−0.0022 (16)	0.0038 (16)	−0.0002 (15)
C11A	0.029 (2)	0.0217 (19)	0.0238 (19)	−0.0052 (17)	0.0027 (17)	−0.0030 (17)
C12A	0.036 (2)	0.030 (2)	0.022 (2)	−0.0030 (18)	0.0017 (18)	−0.0050 (17)
C13A	0.050 (3)	0.025 (2)	0.033 (2)	0.001 (2)	0.016 (2)	0.0028 (18)
C14A	0.045 (3)	0.038 (3)	0.019 (2)	0.000 (2)	0.0018 (19)	0.0070 (18)
C15A	0.034 (2)	0.030 (2)	0.027 (2)	0.0034 (19)	0.0075 (18)	0.0001 (18)
O1B	0.081 (3)	0.0230 (17)	0.0297 (17)	−0.0059 (16)	0.0055 (17)	−0.0043 (14)
O2B	0.064 (2)	0.044 (2)	0.0234 (16)	0.0118 (18)	0.0046 (15)	−0.0008 (14)
O3B	0.0461 (19)	0.0329 (17)	0.0314 (16)	−0.0068 (15)	0.0112 (14)	−0.0119 (14)
C1B	0.032 (2)	0.0202 (19)	0.027 (2)	0.0000 (17)	0.0102 (17)	−0.0037 (16)
C2B	0.044 (3)	0.023 (2)	0.028 (2)	−0.0015 (19)	0.0096 (19)	−0.0015 (18)
C3B	0.046 (3)	0.028 (2)	0.029 (2)	0.002 (2)	0.009 (2)	0.0022 (18)
C4B	0.036 (2)	0.032 (2)	0.027 (2)	0.0004 (19)	0.0077 (18)	−0.0002 (18)
C5B	0.027 (2)	0.030 (2)	0.025 (2)	−0.0014 (18)	0.0079 (17)	−0.0020 (18)
C6B	0.031 (2)	0.023 (2)	0.032 (2)	−0.0035 (18)	0.0092 (18)	−0.0009 (18)
C7B	0.025 (2)	0.022 (2)	0.035 (2)	0.0012 (17)	0.0065 (18)	−0.0022 (17)
C8B	0.035 (2)	0.026 (2)	0.037 (2)	−0.0004 (19)	0.006 (2)	0.0015 (19)
C9B	0.031 (2)	0.032 (2)	0.024 (2)	−0.0024 (19)	0.0017 (17)	0.0003 (18)
C10B	0.028 (2)	0.024 (2)	0.029 (2)	−0.0013 (18)	0.0048 (17)	−0.0038 (17)
C11B	0.043 (3)	0.032 (2)	0.024 (2)	0.001 (2)	0.0022 (19)	−0.0055 (18)
C12B	0.063 (3)	0.026 (2)	0.038 (3)	−0.011 (2)	0.006 (2)	−0.004 (2)
C13B	0.086 (4)	0.028 (2)	0.034 (3)	0.006 (3)	0.013 (3)	0.001 (2)
C14B	0.037 (2)	0.024 (2)	0.044 (3)	−0.0013 (19)	0.006 (2)	−0.0072 (19)
C15B	0.051 (3)	0.029 (2)	0.031 (2)	0.006 (2)	0.008 (2)	−0.0076 (19)
O1C	0.0478 (19)	0.0247 (15)	0.0206 (14)	0.0017 (14)	0.0103 (13)	0.0032 (12)
O2C	0.0460 (19)	0.0268 (17)	0.0431 (19)	0.0019 (14)	0.0085 (16)	0.0098 (15)
O3C	0.0364 (17)	0.0425 (18)	0.0273 (16)	0.0010 (15)	0.0069 (13)	0.0079 (14)
C1C	0.0202 (17)	0.0201 (19)	0.0192 (18)	0.0030 (15)	0.0011 (15)	0.0032 (15)
C2C	0.030 (2)	0.023 (2)	0.0225 (19)	0.0009 (17)	0.0028 (16)	−0.0019 (16)
C3C	0.035 (2)	0.024 (2)	0.030 (2)	0.0029 (18)	0.0077 (18)	−0.0028 (17)
C4C	0.025 (2)	0.029 (2)	0.031 (2)	0.0011 (19)	0.0028 (18)	0.0077 (19)
C5C	0.0195 (19)	0.032 (2)	0.027 (2)	0.0000 (17)	−0.0001 (16)	0.0072 (18)
C6C	0.0252 (19)	0.028 (2)	0.0167 (18)	−0.0012 (17)	0.0016 (15)	0.0031 (15)
C7C	0.0234 (19)	0.035 (2)	0.026 (2)	0.0015 (18)	0.0031 (16)	0.0004 (18)
C8C	0.030 (2)	0.027 (2)	0.031 (2)	−0.0013 (18)	0.0037 (18)	−0.0072 (18)
C9C	0.029 (2)	0.023 (2)	0.031 (2)	−0.0042 (18)	0.0033 (18)	0.0002 (17)
C10C	0.0233 (19)	0.023 (2)	0.023 (2)	0.0024 (16)	0.0020 (16)	0.0020 (16)
C11C	0.027 (2)	0.026 (2)	0.026 (2)	0.0042 (17)	0.0069 (17)	0.0080 (17)
C12C	0.040 (2)	0.026 (2)	0.027 (2)	0.0025 (19)	0.0081 (18)	0.0050 (18)
C13C	0.055 (3)	0.025 (2)	0.033 (2)	0.002 (2)	0.006 (2)	−0.0042 (19)
C14C	0.036 (2)	0.045 (3)	0.0162 (19)	0.004 (2)	0.0069 (17)	−0.0010 (18)
C15C	0.044 (3)	0.025 (2)	0.029 (2)	0.007 (2)	0.0064 (19)	0.0093 (18)
O1D	0.059 (2)	0.0290 (17)	0.0270 (17)	−0.0052 (16)	0.0044 (15)	−0.0035 (13)
O2D	0.0378 (17)	0.0371 (18)	0.0290 (16)	0.0044 (14)	0.0070 (13)	0.0092 (14)
O3D	0.0417 (18)	0.0303 (18)	0.0378 (18)	0.0000 (15)	0.0105 (15)	0.0035 (14)
C1D	0.0200 (19)	0.025 (2)	0.0218 (19)	−0.0001 (16)	0.0006 (15)	0.0025 (16)
C2D	0.032 (2)	0.027 (2)	0.028 (2)	0.0028 (18)	0.0054 (18)	−0.0015 (18)
C3D	0.029 (2)	0.032 (2)	0.028 (2)	0.0044 (18)	0.0040 (18)	0.0018 (18)
C4D	0.0230 (19)	0.039 (3)	0.027 (2)	0.0046 (19)	0.0056 (17)	0.0049 (19)
C5D	0.0233 (19)	0.029 (2)	0.027 (2)	0.0055 (18)	0.0015 (16)	0.0042 (18)
C6D	0.0201 (18)	0.030 (2)	0.026 (2)	0.0022 (17)	0.0037 (16)	−0.0015 (17)
C7D	0.0226 (18)	0.028 (2)	0.029 (2)	0.0035 (17)	0.0014 (16)	0.0006 (18)
C8D	0.027 (2)	0.031 (2)	0.027 (2)	0.0009 (18)	0.0027 (17)	−0.0021 (18)
C9D	0.023 (2)	0.037 (2)	0.022 (2)	0.0035 (18)	0.0043 (16)	0.0012 (17)
C10D	0.026 (2)	0.026 (2)	0.024 (2)	0.0007 (17)	0.0022 (16)	0.0015 (17)
C11D	0.034 (2)	0.025 (2)	0.029 (2)	−0.0011 (18)	0.0035 (18)	0.0031 (17)
C12D	0.053 (3)	0.024 (2)	0.032 (2)	0.004 (2)	0.006 (2)	0.0002 (19)
C13D	0.055 (3)	0.035 (3)	0.031 (2)	0.002 (2)	0.011 (2)	−0.003 (2)
C14D	0.037 (2)	0.021 (2)	0.036 (2)	0.0029 (18)	0.0053 (19)	−0.0009 (18)
C15D	0.043 (3)	0.026 (2)	0.031 (2)	0.002 (2)	0.007 (2)	0.0071 (18)

Geometric parameters (Å, º) top

O1A—C2A	1.354 (5)	O1C—C2C	1.351 (5)
O1A—C12A	1.450 (5)	O1C—C12C	1.448 (5)
O2A—C4A	1.221 (5)	O2C—C4C	1.227 (5)
O3A—C5A	1.204 (5)	O3C—C5C	1.214 (5)
C1A—C10A	1.391 (6)	C1C—C10C	1.394 (6)
C1A—C6A	1.422 (5)	C1C—C6C	1.430 (5)
C1A—C2A	1.463 (5)	C1C—C2C	1.480 (6)
C2A—C3A	1.369 (6)	C2C—C3C	1.361 (6)
C3A—C4A	1.445 (6)	C3C—C4C	1.449 (6)
C3A—C13A	1.505 (6)	C3C—C13C	1.504 (6)
C4A—C5A	1.559 (6)	C4C—C5C	1.536 (6)
C5A—C6A	1.477 (6)	C5C—C6C	1.490 (6)
C6A—C7A	1.407 (6)	C6C—C7C	1.398 (6)
C7A—C8A	1.391 (6)	C7C—C8C	1.394 (6)
C7A—C14A	1.506 (6)	C7C—C14C	1.517 (6)
C8A—C9A	1.374 (6)	C8C—C9C	1.377 (6)
C8A—H8AA	0.93	C8C—H8CA	0.93
C9A—C10A	1.407 (6)	C9C—C10C	1.404 (6)
C9A—H9AA	0.93	C9C—H9CA	0.93
C10A—C11A	1.515 (5)	C10C—C11C	1.507 (5)
C11A—C12A	1.505 (6)	C11C—C12C	1.512 (6)
C11A—C15A	1.540 (6)	C11C—C15C	1.534 (6)
C11A—H11A	0.98	C11C—H11C	0.98
C12A—H12A	0.97	C12C—H12E	0.97
C12A—H12B	0.97	C12C—H12F	0.97
C13A—H13A	0.96	C13C—H13G	0.96
C13A—H13B	0.96	C13C—H13H	0.96
C13A—H13C	0.96	C13C—H13I	0.96
C14A—H14A	0.96	C14C—H14G	0.96
C14A—H14B	0.96	C14C—H14H	0.96
C14A—H14C	0.96	C14C—H14I	0.96
C15A—H15A	0.96	C15C—H15G	0.96
C15A—H15B	0.96	C15C—H15H	0.96
C15A—H15C	0.96	C15C—H15I	0.96
O1B—C2B	1.347 (5)	O1D—C2D	1.359 (5)
O1B—C12B	1.452 (6)	O1D—C12D	1.448 (5)
O2B—C4B	1.226 (5)	O2D—C4D	1.227 (5)
O3B—C5B	1.207 (5)	O3D—C5D	1.211 (5)
C1B—C10B	1.400 (6)	C1D—C10D	1.404 (6)
C1B—C6B	1.424 (6)	C1D—C6D	1.428 (6)
C1B—C2B	1.467 (6)	C1D—C2D	1.464 (6)
C2B—C3B	1.360 (6)	C2D—C3D	1.349 (6)
C3B—C4B	1.424 (6)	C3D—C4D	1.430 (6)
C3B—C13B	1.495 (7)	C3D—C13D	1.523 (6)
C4B—C5B	1.551 (6)	C4D—C5D	1.551 (6)
C5B—C6B	1.500 (6)	C5D—C6D	1.493 (6)
C6B—C7B	1.403 (6)	C6D—C7D	1.407 (6)
C7B—C8B	1.399 (6)	C7D—C8D	1.393 (6)
C7B—C14B	1.499 (6)	C7D—C14D	1.504 (6)
C8B—C9B	1.373 (6)	C8D—C9D	1.389 (6)
C8B—H8BA	0.93	C8D—H8DA	0.93
C9B—C10B	1.383 (6)	C9D—C10D	1.396 (6)
C9B—H9BA	0.93	C9D—H9DA	0.93
C10B—C11B	1.496 (6)	C10D—C11D	1.512 (6)
C11B—C12B	1.502 (6)	C11D—C12D	1.504 (6)
C11B—C15B	1.524 (6)	C11D—C15D	1.532 (6)
C11B—H11B	0.98	C11D—H11D	0.98
C12B—H12C	0.97	C12D—H12G	0.97
C12B—H12D	0.97	C12D—H12H	0.97
C13B—H13D	0.96	C13D—H13J	0.96
C13B—H13E	0.96	C13D—H13K	0.96
C13B—H13F	0.96	C13D—H13L	0.96
C14B—H14D	0.96	C14D—H14J	0.96
C14B—H14E	0.96	C14D—H14K	0.96
C14B—H14F	0.96	C14D—H14L	0.96
C15B—H15D	0.96	C15D—H15J	0.96
C15B—H15E	0.96	C15D—H15K	0.96
C15B—H15F	0.96	C15D—H15L	0.96

C2A—O1A—C12A	116.5 (3)	C2C—O1C—C12C	116.7 (3)
C10A—C1A—C6A	120.4 (3)	C10C—C1C—C6C	120.5 (4)
C10A—C1A—C2A	119.2 (3)	C10C—C1C—C2C	119.5 (3)
C6A—C1A—C2A	120.3 (3)	C6C—C1C—C2C	120.0 (3)
O1A—C2A—C3A	115.9 (3)	O1C—C2C—C3C	116.4 (4)
O1A—C2A—C1A	119.0 (3)	O1C—C2C—C1C	118.1 (3)
C3A—C2A—C1A	125.0 (4)	C3C—C2C—C1C	125.4 (4)
C2A—C3A—C4A	118.5 (4)	C2C—C3C—C4C	117.7 (4)
C2A—C3A—C13A	122.5 (4)	C2C—C3C—C13C	123.6 (4)
C4A—C3A—C13A	119.0 (4)	C4C—C3C—C13C	118.7 (4)
O2A—C4A—C3A	123.7 (4)	O2C—C4C—C3C	122.0 (4)
O2A—C4A—C5A	117.3 (4)	O2C—C4C—C5C	117.7 (4)
C3A—C4A—C5A	118.9 (4)	C3C—C4C—C5C	120.3 (4)
O3A—C5A—C6A	124.7 (4)	O3C—C5C—C6C	123.9 (4)
O3A—C5A—C4A	116.8 (4)	O3C—C5C—C4C	117.5 (4)
C6A—C5A—C4A	118.5 (3)	C6C—C5C—C4C	118.6 (3)
C7A—C6A—C1A	119.9 (4)	C7C—C6C—C1C	120.4 (4)
C7A—C6A—C5A	121.9 (3)	C7C—C6C—C5C	122.0 (4)
C1A—C6A—C5A	118.2 (3)	C1C—C6C—C5C	117.6 (4)
C8A—C7A—C6A	118.1 (4)	C8C—C7C—C6C	117.8 (4)
C8A—C7A—C14A	118.8 (4)	C8C—C7C—C14C	118.2 (4)
C6A—C7A—C14A	123.1 (4)	C6C—C7C—C14C	124.0 (4)
C9A—C8A—C7A	122.3 (4)	C9C—C8C—C7C	122.1 (4)
C9A—C8A—H8AA	118.8	C9C—C8C—H8CA	118.9
C7A—C8A—H8AA	118.8	C7C—C8C—H8CA	118.9
C8A—C9A—C10A	120.3 (4)	C8C—C9C—C10C	121.1 (4)
C8A—C9A—H9AA	119.9	C8C—C9C—H9CA	119.4
C10A—C9A—H9AA	119.9	C10C—C9C—H9CA	119.4
C1A—C10A—C9A	118.9 (4)	C1C—C10C—C9C	118.0 (4)
C1A—C10A—C11A	120.5 (3)	C1C—C10C—C11C	120.7 (4)
C9A—C10A—C11A	120.6 (4)	C9C—C10C—C11C	121.2 (4)
C12A—C11A—C10A	108.1 (3)	C10C—C11C—C12C	107.9 (3)
C12A—C11A—C15A	112.7 (4)	C10C—C11C—C15C	114.0 (3)
C10A—C11A—C15A	111.9 (3)	C12C—C11C—C15C	108.9 (3)
C12A—C11A—H11A	108.0	C10C—C11C—H11C	108.6
C10A—C11A—H11A	108.0	C12C—C11C—H11C	108.6
C15A—C11A—H11A	108.0	C15C—C11C—H11C	108.6
O1A—C12A—C11A	111.2 (3)	O1C—C12C—C11C	111.7 (3)
O1A—C12A—H12A	109.4	O1C—C12C—H12E	109.3
C11A—C12A—H12A	109.4	C11C—C12C—H12E	109.3
O1A—C12A—H12B	109.4	O1C—C12C—H12F	109.3
C11A—C12A—H12B	109.4	C11C—C12C—H12F	109.3
H12A—C12A—H12B	108.0	H12E—C12C—H12F	107.9
C3A—C13A—H13A	109.5	C3C—C13C—H13G	109.5
C3A—C13A—H13B	109.5	C3C—C13C—H13H	109.5
H13A—C13A—H13B	109.5	H13G—C13C—H13H	109.5
C3A—C13A—H13C	109.5	C3C—C13C—H13I	109.5
H13A—C13A—H13C	109.5	H13G—C13C—H13I	109.5
H13B—C13A—H13C	109.5	H13H—C13C—H13I	109.5
C7A—C14A—H14A	109.5	C7C—C14C—H14G	109.5
C7A—C14A—H14B	109.5	C7C—C14C—H14H	109.5
H14A—C14A—H14B	109.5	H14G—C14C—H14H	109.5
C7A—C14A—H14C	109.5	C7C—C14C—H14I	109.5
H14A—C14A—H14C	109.5	H14G—C14C—H14I	109.5
H14B—C14A—H14C	109.5	H14H—C14C—H14I	109.5
C11A—C15A—H15A	109.5	C11C—C15C—H15G	109.5
C11A—C15A—H15B	109.5	C11C—C15C—H15H	109.5
H15A—C15A—H15B	109.5	H15G—C15C—H15H	109.5
C11A—C15A—H15C	109.5	C11C—C15C—H15I	109.5
H15A—C15A—H15C	109.5	H15G—C15C—H15I	109.5
H15B—C15A—H15C	109.5	H15H—C15C—H15I	109.5
C2B—O1B—C12B	117.1 (4)	C2D—O1D—C12D	117.1 (3)
C10B—C1B—C6B	119.9 (4)	C10D—C1D—C6D	120.0 (4)
C10B—C1B—C2B	119.6 (4)	C10D—C1D—C2D	119.8 (4)
C6B—C1B—C2B	120.5 (4)	C6D—C1D—C2D	120.1 (4)
O1B—C2B—C3B	117.4 (4)	C3D—C2D—O1D	117.1 (4)
O1B—C2B—C1B	118.0 (4)	C3D—C2D—C1D	125.1 (4)
C3B—C2B—C1B	124.5 (4)	O1D—C2D—C1D	117.7 (4)
C2B—C3B—C4B	119.1 (4)	C2D—C3D—C4D	118.9 (4)
C2B—C3B—C13B	122.4 (4)	C2D—C3D—C13D	123.4 (4)
C4B—C3B—C13B	118.5 (4)	C4D—C3D—C13D	117.7 (4)
O2B—C4B—C3B	123.1 (4)	O2D—C4D—C3D	122.8 (4)
O2B—C4B—C5B	117.1 (4)	O2D—C4D—C5D	117.2 (4)
C3B—C4B—C5B	119.8 (4)	C3D—C4D—C5D	120.0 (4)
O3B—C5B—C6B	123.9 (4)	O3D—C5D—C6D	124.6 (4)
O3B—C5B—C4B	118.3 (4)	O3D—C5D—C4D	117.7 (4)
C6B—C5B—C4B	117.8 (4)	C6D—C5D—C4D	117.6 (4)
C7B—C6B—C1B	120.7 (4)	C7D—C6D—C1D	120.6 (4)
C7B—C6B—C5B	121.8 (4)	C7D—C6D—C5D	121.4 (4)
C1B—C6B—C5B	117.5 (4)	C1D—C6D—C5D	117.9 (4)
C8B—C7B—C6B	117.6 (4)	C8D—C7D—C6D	117.7 (4)
C8B—C7B—C14B	118.4 (4)	C8D—C7D—C14D	118.0 (4)
C6B—C7B—C14B	124.0 (4)	C6D—C7D—C14D	124.2 (4)
C9B—C8B—C7B	121.2 (4)	C9D—C8D—C7D	122.0 (4)
C9B—C8B—H8BA	119.4	C9D—C8D—H8DA	119.0
C7B—C8B—H8BA	119.4	C7D—C8D—H8DA	119.0
C8B—C9B—C10B	122.3 (4)	C8D—C9D—C10D	121.1 (4)
C8B—C9B—H9BA	118.8	C8D—C9D—H9DA	119.4
C10B—C9B—H9BA	118.8	C10D—C9D—H9DA	119.4
C9B—C10B—C1B	118.1 (4)	C9D—C10D—C1D	118.4 (4)
C9B—C10B—C11B	121.4 (4)	C9D—C10D—C11D	120.5 (4)
C1B—C10B—C11B	120.5 (4)	C1D—C10D—C11D	121.1 (4)
C10B—C11B—C12B	107.9 (4)	C12D—C11D—C10D	109.0 (4)
C10B—C11B—C15B	110.9 (4)	C12D—C11D—C15D	108.0 (4)
C12B—C11B—C15B	113.6 (4)	C10D—C11D—C15D	114.2 (4)
C10B—C11B—H11B	108.1	C12D—C11D—H11D	108.5
C12B—C11B—H11B	108.1	C10D—C11D—H11D	108.5
C15B—C11B—H11B	108.1	C15D—C11D—H11D	108.5
O1B—C12B—C11B	111.2 (4)	O1D—C12D—C11D	112.7 (4)
O1B—C12B—H12C	109.4	O1D—C12D—H12G	109.1
C11B—C12B—H12C	109.4	C11D—C12D—H12G	109.1
O1B—C12B—H12D	109.4	O1D—C12D—H12H	109.1
C11B—C12B—H12D	109.4	C11D—C12D—H12H	109.1
H12C—C12B—H12D	108.0	H12G—C12D—H12H	107.8
C3B—C13B—H13D	109.5	C3D—C13D—H13J	109.5
C3B—C13B—H13E	109.5	C3D—C13D—H13K	109.5
H13D—C13B—H13E	109.5	H13J—C13D—H13K	109.5
C3B—C13B—H13F	109.5	C3D—C13D—H13L	109.5
H13D—C13B—H13F	109.5	H13J—C13D—H13L	109.5
H13E—C13B—H13F	109.5	H13K—C13D—H13L	109.5
C7B—C14B—H14D	109.5	C7D—C14D—H14J	109.5
C7B—C14B—H14E	109.5	C7D—C14D—H14K	109.5
H14D—C14B—H14E	109.5	H14J—C14D—H14K	109.5
C7B—C14B—H14F	109.5	C7D—C14D—H14L	109.5
H14D—C14B—H14F	109.5	H14J—C14D—H14L	109.5
H14E—C14B—H14F	109.5	H14K—C14D—H14L	109.5
C11B—C15B—H15D	109.5	C11D—C15D—H15J	109.5
C11B—C15B—H15E	109.5	C11D—C15D—H15K	109.5
H15D—C15B—H15E	109.5	H15J—C15D—H15K	109.5
C11B—C15B—H15F	109.5	C11D—C15D—H15L	109.5
H15D—C15B—H15F	109.5	H15J—C15D—H15L	109.5
H15E—C15B—H15F	109.5	H15K—C15D—H15L	109.5

C12A—O1A—C2A—C3A	158.0 (4)	C12C—O1C—C2C—C3C	−157.6 (4)
C12A—O1A—C2A—C1A	−24.9 (5)	C12C—O1C—C2C—C1C	25.8 (5)
C10A—C1A—C2A—O1A	−4.0 (5)	C10C—C1C—C2C—O1C	3.4 (6)
C6A—C1A—C2A—O1A	177.3 (3)	C6C—C1C—C2C—O1C	−179.2 (3)
C10A—C1A—C2A—C3A	172.8 (4)	C10C—C1C—C2C—C3C	−172.9 (4)
C6A—C1A—C2A—C3A	−6.0 (6)	C6C—C1C—C2C—C3C	4.5 (6)
O1A—C2A—C3A—C4A	−179.6 (3)	O1C—C2C—C3C—C4C	180.0 (4)
C1A—C2A—C3A—C4A	3.5 (6)	C1C—C2C—C3C—C4C	−3.6 (7)
O1A—C2A—C3A—C13A	−1.8 (6)	O1C—C2C—C3C—C13C	1.0 (7)
C1A—C2A—C3A—C13A	−178.7 (4)	C1C—C2C—C3C—C13C	177.4 (4)
C2A—C3A—C4A—O2A	−179.6 (4)	C2C—C3C—C4C—O2C	179.8 (4)
C13A—C3A—C4A—O2A	2.5 (7)	C13C—C3C—C4C—O2C	−1.2 (7)
C2A—C3A—C4A—C5A	3.8 (6)	C2C—C3C—C4C—C5C	−2.0 (6)
C13A—C3A—C4A—C5A	−174.1 (4)	C13C—C3C—C4C—C5C	177.0 (4)
O2A—C4A—C5A—O3A	−6.2 (6)	O2C—C4C—C5C—O3C	6.6 (6)
C3A—C4A—C5A—O3A	170.7 (4)	C3C—C4C—C5C—O3C	−171.7 (4)
O2A—C4A—C5A—C6A	174.4 (4)	O2C—C4C—C5C—C6C	−175.0 (4)
C3A—C4A—C5A—C6A	−8.7 (6)	C3C—C4C—C5C—C6C	6.7 (6)
C10A—C1A—C6A—C7A	0.9 (6)	C10C—C1C—C6C—C7C	0.2 (6)
C2A—C1A—C6A—C7A	179.7 (4)	C2C—C1C—C6C—C7C	−177.1 (4)
C10A—C1A—C6A—C5A	−178.3 (4)	C10C—C1C—C6C—C5C	178.1 (4)
C2A—C1A—C6A—C5A	0.4 (5)	C2C—C1C—C6C—C5C	0.7 (5)
O3A—C5A—C6A—C7A	7.8 (6)	O3C—C5C—C6C—C7C	−9.7 (6)
C4A—C5A—C6A—C7A	−172.8 (4)	C4C—C5C—C6C—C7C	171.9 (4)
O3A—C5A—C6A—C1A	−173.0 (4)	O3C—C5C—C6C—C1C	172.5 (4)
C4A—C5A—C6A—C1A	6.4 (5)	C4C—C5C—C6C—C1C	−5.8 (5)
C1A—C6A—C7A—C8A	−1.2 (6)	C1C—C6C—C7C—C8C	−0.9 (6)
C5A—C6A—C7A—C8A	178.0 (4)	C5C—C6C—C7C—C8C	−178.6 (4)
C1A—C6A—C7A—C14A	178.8 (4)	C1C—C6C—C7C—C14C	178.5 (4)
C5A—C6A—C7A—C14A	−2.0 (6)	C5C—C6C—C7C—C14C	0.8 (6)
C6A—C7A—C8A—C9A	1.0 (6)	C6C—C7C—C8C—C9C	1.4 (6)
C14A—C7A—C8A—C9A	−179.0 (4)	C14C—C7C—C8C—C9C	−178.0 (4)
C7A—C8A—C9A—C10A	−0.5 (7)	C7C—C8C—C9C—C10C	−1.3 (6)
C6A—C1A—C10A—C9A	−0.3 (6)	C6C—C1C—C10C—C9C	−0.1 (6)
C2A—C1A—C10A—C9A	−179.1 (4)	C2C—C1C—C10C—C9C	177.3 (4)
C6A—C1A—C10A—C11A	179.9 (3)	C6C—C1C—C10C—C11C	−178.8 (4)
C2A—C1A—C10A—C11A	1.2 (5)	C2C—C1C—C10C—C11C	−1.4 (6)
C8A—C9A—C10A—C1A	0.1 (6)	C8C—C9C—C10C—C1C	0.5 (6)
C8A—C9A—C10A—C11A	179.8 (4)	C8C—C9C—C10C—C11C	179.3 (4)
C1A—C10A—C11A—C12A	27.4 (5)	C1C—C10C—C11C—C12C	−26.4 (5)
C9A—C10A—C11A—C12A	−152.4 (4)	C9C—C10C—C11C—C12C	154.9 (4)
C1A—C10A—C11A—C15A	−97.3 (4)	C1C—C10C—C11C—C15C	−147.6 (4)
C9A—C10A—C11A—C15A	83.0 (5)	C9C—C10C—C11C—C15C	33.7 (5)
C2A—O1A—C12A—C11A	55.5 (5)	C2C—O1C—C12C—C11C	−56.1 (5)
C10A—C11A—C12A—O1A	−53.7 (4)	C10C—C11C—C12C—O1C	53.4 (4)
C15A—C11A—C12A—O1A	70.5 (4)	C15C—C11C—C12C—O1C	177.7 (3)
C12B—O1B—C2B—C3B	159.2 (4)	C12D—O1D—C2D—C3D	−154.7 (4)
C12B—O1B—C2B—C1B	−24.6 (6)	C12D—O1D—C2D—C1D	28.8 (6)
C10B—C1B—C2B—O1B	−3.8 (6)	C10D—C1D—C2D—C3D	−175.0 (4)
C6B—C1B—C2B—O1B	176.5 (4)	C6D—C1D—C2D—C3D	3.6 (7)
C10B—C1B—C2B—C3B	172.1 (4)	C10D—C1D—C2D—O1D	1.3 (6)
C6B—C1B—C2B—C3B	−7.7 (7)	C6D—C1D—C2D—O1D	179.9 (4)
O1B—C2B—C3B—C4B	−179.1 (4)	O1D—C2D—C3D—C4D	−177.8 (4)
C1B—C2B—C3B—C4B	5.0 (7)	C1D—C2D—C3D—C4D	−1.5 (7)
O1B—C2B—C3B—C13B	−1.9 (7)	O1D—C2D—C3D—C13D	1.2 (7)
C1B—C2B—C3B—C13B	−177.8 (5)	C1D—C2D—C3D—C13D	177.5 (4)
C2B—C3B—C4B—O2B	−179.7 (4)	C2D—C3D—C4D—O2D	178.6 (4)
C13B—C3B—C4B—O2B	3.0 (7)	C13D—C3D—C4D—O2D	−0.5 (7)
C2B—C3B—C4B—C5B	3.2 (6)	C2D—C3D—C4D—C5D	−3.0 (6)
C13B—C3B—C4B—C5B	−174.1 (4)	C13D—C3D—C4D—C5D	177.9 (4)
O2B—C4B—C5B—O3B	−5.9 (6)	O2D—C4D—C5D—O3D	3.0 (6)
C3B—C4B—C5B—O3B	171.4 (4)	C3D—C4D—C5D—O3D	−175.5 (4)
O2B—C4B—C5B—C6B	174.0 (4)	O2D—C4D—C5D—C6D	−176.1 (4)
C3B—C4B—C5B—C6B	−8.7 (6)	C3D—C4D—C5D—C6D	5.4 (6)
C10B—C1B—C6B—C7B	−0.1 (6)	C10D—C1D—C6D—C7D	0.3 (6)
C2B—C1B—C6B—C7B	179.7 (4)	C2D—C1D—C6D—C7D	−178.3 (4)
C10B—C1B—C6B—C5B	−178.3 (4)	C10D—C1D—C6D—C5D	177.7 (4)
C2B—C1B—C6B—C5B	1.5 (6)	C2D—C1D—C6D—C5D	−0.9 (6)
O3B—C5B—C6B—C7B	7.8 (7)	O3D—C5D—C6D—C7D	−4.9 (6)
C4B—C5B—C6B—C7B	−172.1 (4)	C4D—C5D—C6D—C7D	174.1 (4)
O3B—C5B—C6B—C1B	−174.0 (4)	O3D—C5D—C6D—C1D	177.7 (4)
C4B—C5B—C6B—C1B	6.1 (6)	C4D—C5D—C6D—C1D	−3.3 (5)
C1B—C6B—C7B—C8B	−1.5 (6)	C1D—C6D—C7D—C8D	1.1 (6)
C5B—C6B—C7B—C8B	176.6 (4)	C5D—C6D—C7D—C8D	−176.3 (4)
C1B—C6B—C7B—C14B	179.4 (4)	C1D—C6D—C7D—C14D	−177.1 (4)
C5B—C6B—C7B—C14B	−2.4 (6)	C5D—C6D—C7D—C14D	5.5 (6)
C6B—C7B—C8B—C9B	0.9 (6)	C6D—C7D—C8D—C9D	−0.3 (6)
C14B—C7B—C8B—C9B	180.0 (4)	C14D—C7D—C8D—C9D	178.0 (4)
C7B—C8B—C9B—C10B	1.4 (7)	C7D—C8D—C9D—C10D	−1.8 (7)
C8B—C9B—C10B—C1B	−3.0 (6)	C8D—C9D—C10D—C1D	3.2 (6)
C8B—C9B—C10B—C11B	179.3 (4)	C8D—C9D—C10D—C11D	−176.3 (4)
C6B—C1B—C10B—C9B	2.3 (6)	C6D—C1D—C10D—C9D	−2.4 (6)
C2B—C1B—C10B—C9B	−177.5 (4)	C2D—C1D—C10D—C9D	176.2 (4)
C6B—C1B—C10B—C11B	−180.0 (4)	C6D—C1D—C10D—C11D	177.1 (4)
C2B—C1B—C10B—C11B	0.3 (6)	C2D—C1D—C10D—C11D	−4.3 (6)
C9B—C10B—C11B—C12B	−153.9 (4)	C9D—C10D—C11D—C12D	159.1 (4)
C1B—C10B—C11B—C12B	28.5 (6)	C1D—C10D—C11D—C12D	−20.4 (6)
C9B—C10B—C11B—C15B	81.2 (5)	C9D—C10D—C11D—C15D	38.3 (6)
C1B—C10B—C11B—C15B	−96.5 (5)	C1D—C10D—C11D—C15D	−141.2 (4)
C2B—O1B—C12B—C11B	55.7 (6)	C2D—O1D—C12D—C11D	−55.5 (5)
C10B—C11B—C12B—O1B	−54.3 (5)	C10D—C11D—C12D—O1D	48.1 (5)
C15B—C11B—C12B—O1B	69.0 (5)	C15D—C11D—C12D—O1D	172.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9C—H9CA···O2Cⁱ	0.93	2.45	3.185 (5)	136
C8D—H8DA···O2Bⁱⁱ	0.93	2.43	3.352 (5)	169
C11D—H11D···O2Cⁱⁱ	0.98	2.55	3.449 (5)	152
C12A—H12A···O3Bⁱⁱ	0.97	2.43	3.248 (5)	142
C12C—H12E···O3Aⁱⁱⁱ	0.97	2.43	3.368 (5)	162
C12C—H12F···O2D	0.97	2.43	3.349 (5)	158
C12D—H12G···O3D^iv	0.97	2.46	3.343 (5)	151
C12D—H12H···O2C	0.97	2.51	3.358 (6)	146
C14B—H14F···O1B^v	0.96	2.56	3.273 (5)	131
C15A—H15B···O3B	0.96	2.52	3.410 (5)	154

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

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