A new triclinic polymorph of 4-n-hexyl­oxybenzoic acid

The title new triclinic polymorph of 4-n-hexyl­oxybenzoic acid, C₁₃H₁₈O₃, crystallizes with six independent mol­ecules in the asymmetric unit. Four of these have the hydroxyl group arranged cis to the methyl­ene group attached to the ether O atom, whereas in two mol­ecules the carbonyl group is cis to the methyl­ene group at the ether O atom. All mol­ecules form hydrogen-bonded dimers through the carboxylic acid functionalities. The cell parameters for what appears to be the title polymorph had been originally inaccurately determined as monoclinic [a = 14.5 Å, b = 33.0 Å, c = 8.0 Å, α = 90.0°, β = 93.0° and γ = 90.0°; Bryan (1960). J. Chem. Soc. pp. 2517–2519]; no space group was given and no atomic coordinates were available. The other polymorph known for the title compound is a Z′ = 1 phase crystallizing in P2₁/c [Bryan et al. (1980). Mol. Cryst. Liq. Cryst. 62, 311–326].

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.076
• wR factor = 0.202
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.66 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

4-n-hexyloxybenzoic acid

Crystal data

C13H18O3	Z = 12
Mr = 222.27	F(000) = 1440
Triclinic, P1	Dx = 1.180 Mg m^−3
Hall symbol: -P 1	Melting point: 365 K
a = 7.9679 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.4604 (18) Å	Cell parameters from 13551 reflections
c = 33.389 (4) Å	θ = 3.5–25.7°
α = 88.809 (10)°	µ = 0.08 mm^−1
β = 85.795 (9)°	T = 173 K
γ = 78.015 (9)°	Block, colourless
V = 3753.0 (8) Å^3	0.35 × 0.33 × 0.32 mm

Data collection

Stoe IPDS-II two-circle diffractometer	10358 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
Graphite monochromator	θmax = 25.7°, θmin = 3.5°
ω scans	h = −9→9
31668 measured reflections	k = −17→17
13939 independent reflections	l = 0→40

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.076	H-atom parameters constrained
wR(F^2) = 0.202	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 7.8018P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
13939 reflections	Δρmax = 0.23 e Å^−3
872 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (2)

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

	x	y	z	Uiso*/Ueq
O1	0.6525 (3)	0.93383 (18)	0.77442 (7)	0.0354 (6)
O2	0.3831 (3)	1.04081 (18)	0.95656 (8)	0.0372 (6)
H2	0.3754	1.0364	0.9817	0.045*
O3	0.6473 (3)	0.95227 (19)	0.96431 (8)	0.0388 (6)
C1	0.6084 (4)	0.9492 (2)	0.81456 (10)	0.0292 (7)
C2	0.4565 (4)	1.0074 (2)	0.83057 (11)	0.0309 (7)
H2F	0.3722	1.0383	0.8134	0.037*
C3	0.4302 (4)	1.0194 (2)	0.87246 (10)	0.0307 (7)
H3	0.3272	1.0589	0.8833	0.037*
C4	0.5515 (4)	0.9748 (2)	0.89830 (10)	0.0294 (7)
C5	0.7015 (4)	0.9153 (2)	0.88189 (11)	0.0318 (7)
H5	0.7848	0.8836	0.8992	0.038*
C6	0.7299 (4)	0.9022 (2)	0.84064 (10)	0.0323 (7)
H6	0.8319	0.8613	0.8300	0.039*
C7	0.5290 (4)	0.9893 (2)	0.94240 (10)	0.0310 (7)
C11	0.5348 (4)	0.9804 (2)	0.74593 (10)	0.0310 (7)
H11A	0.5128	1.0498	0.7495	0.037*
H11B	0.4239	0.9597	0.7500	0.037*
C12	0.6179 (4)	0.9538 (3)	0.70382 (10)	0.0322 (7)
H12A	0.7256	0.9778	0.6997	0.039*
H12B	0.6478	0.8841	0.7014	0.039*
C13	0.4981 (5)	0.9946 (3)	0.67145 (11)	0.0359 (8)
H13A	0.4678	1.0642	0.6741	0.043*
H13B	0.3906	0.9705	0.6757	0.043*
C14	0.5777 (5)	0.9696 (3)	0.62873 (11)	0.0425 (9)
H14A	0.6852	0.9937	0.6245	0.051*
H14B	0.6080	0.8999	0.6261	0.051*
C15	0.4572 (6)	1.0106 (3)	0.59625 (12)	0.0543 (11)
H15A	0.3524	0.9838	0.5999	0.065*
H15B	0.4218	1.0798	0.6001	0.065*
C16	0.5344 (7)	0.9918 (4)	0.55361 (14)	0.0720 (15)
H16A	0.4495	1.0201	0.5347	0.108*
H16B	0.5670	0.9234	0.5492	0.108*
H16C	0.6365	1.0196	0.5494	0.108*
O1A	0.6721 (3)	0.42694 (18)	0.72060 (7)	0.0361 (6)
O2A	0.3826 (3)	0.53077 (19)	0.54769 (8)	0.0378 (6)
H2A	0.3789	0.5341	0.5226	0.045*
O3A	0.6456 (3)	0.44349 (19)	0.53036 (8)	0.0395 (6)
C1A	0.6253 (4)	0.4427 (2)	0.68159 (10)	0.0294 (7)
C2A	0.4741 (4)	0.5013 (2)	0.67058 (11)	0.0337 (8)
H2G	0.3927	0.5330	0.6906	0.040*
C3A	0.4419 (4)	0.5138 (2)	0.63000 (11)	0.0330 (8)
H3A	0.3391	0.5545	0.6226	0.040*
C4A	0.5596 (4)	0.4669 (2)	0.60024 (10)	0.0299 (7)
C5A	0.7090 (4)	0.4076 (3)	0.61139 (11)	0.0340 (8)
H5A	0.7902	0.3760	0.5913	0.041*
C6A	0.7416 (4)	0.3937 (3)	0.65162 (11)	0.0354 (8)
H6A	0.8425	0.3512	0.6589	0.042*
C7A	0.5306 (4)	0.4800 (2)	0.55669 (11)	0.0310 (7)
C11A	0.5570 (4)	0.4746 (3)	0.75254 (11)	0.0335 (8)
H11C	0.4446	0.4555	0.7528	0.040*
H11D	0.5378	0.5439	0.7484	0.040*
C12A	0.6368 (5)	0.4482 (3)	0.79236 (11)	0.0342 (8)
H12C	0.6589	0.3786	0.7958	0.041*
H12D	0.7486	0.4681	0.7919	0.041*
C13A	0.5208 (5)	0.4943 (3)	0.82759 (11)	0.0377 (8)
H13C	0.4080	0.4760	0.8272	0.045*
H13D	0.5014	0.5638	0.8241	0.045*
C14A	0.5917 (5)	0.4682 (3)	0.86877 (11)	0.0418 (9)
H14C	0.6079	0.3990	0.8727	0.050*
H14D	0.7058	0.4852	0.8691	0.050*
C15A	0.4742 (6)	0.5178 (3)	0.90363 (13)	0.0526 (11)
H15C	0.4595	0.5870	0.8998	0.063*
H15D	0.3596	0.5017	0.9029	0.063*
C16A	0.5421 (7)	0.4912 (4)	0.94487 (13)	0.0674 (14)
H16D	0.4603	0.5244	0.9658	0.101*
H16E	0.6534	0.5092	0.9462	0.101*
H16F	0.5560	0.4228	0.9490	0.101*
O1B	0.7664 (3)	0.66913 (18)	0.60958 (7)	0.0347 (6)
O2B	0.8804 (3)	0.62266 (19)	0.41897 (8)	0.0403 (6)
H2B	0.8659	0.6320	0.3944	0.048*
O3B	0.6156 (3)	0.71392 (19)	0.42518 (8)	0.0388 (6)
C1B	0.7747 (4)	0.6629 (2)	0.56864 (10)	0.0281 (7)
C2B	0.9182 (4)	0.6180 (2)	0.54393 (10)	0.0290 (7)
H2H	1.0203	0.5865	0.5555	0.035*
C3B	0.9089 (4)	0.6203 (2)	0.50232 (10)	0.0278 (7)
H3B	1.0060	0.5906	0.4856	0.033*
C4B	0.7591 (4)	0.6655 (2)	0.48472 (10)	0.0278 (7)
C5B	0.6162 (4)	0.7083 (3)	0.50983 (10)	0.0328 (7)
H5B	0.5133	0.7384	0.4983	0.039*
C6B	0.6229 (4)	0.7073 (3)	0.55107 (10)	0.0340 (8)
H6B	0.5250	0.7367	0.5676	0.041*
C7B	0.7468 (4)	0.6692 (2)	0.44024 (10)	0.0297 (7)
C11B	0.9114 (4)	0.6234 (2)	0.63170 (10)	0.0287 (7)
H11E	1.0150	0.6483	0.6231	0.034*
H11F	0.9369	0.5542	0.6273	0.034*
C12B	0.8577 (4)	0.6457 (2)	0.67546 (10)	0.0292 (7)
H12E	0.7572	0.6173	0.6834	0.035*
H12F	0.8204	0.7151	0.6783	0.035*
C13B	0.9986 (4)	0.6101 (2)	0.70454 (10)	0.0288 (7)
H13E	1.0369	0.5407	0.7018	0.035*
H13F	1.0988	0.6390	0.6971	0.035*
C14B	0.9366 (5)	0.6337 (3)	0.74834 (11)	0.0353 (8)
H14E	0.8371	0.6041	0.7557	0.042*
H14F	0.8961	0.7030	0.7507	0.042*
C15B	1.0739 (5)	0.6009 (3)	0.77837 (11)	0.0372 (8)
H15E	1.1167	0.5318	0.7754	0.045*
H15F	1.1720	0.6319	0.7715	0.045*
C16B	1.0120 (6)	0.6217 (3)	0.82185 (12)	0.0552 (11)
H16G	1.1063	0.5980	0.8391	0.083*
H16H	0.9161	0.5904	0.8292	0.083*
H16I	0.9734	0.6901	0.8254	0.083*
O1C	0.6969 (3)	0.72057 (17)	0.15505 (7)	0.0341 (5)
O2C	0.5880 (3)	0.73733 (18)	0.34596 (7)	0.0378 (6)
H2C	0.6029	0.7286	0.3705	0.045*
O3C	0.8482 (3)	0.64003 (18)	0.34021 (8)	0.0374 (6)
C1C	0.7137 (4)	0.7104 (2)	0.19592 (10)	0.0271 (7)
C2C	0.8625 (4)	0.6645 (2)	0.21343 (10)	0.0281 (7)
H2I	0.9625	0.6372	0.1971	0.034*
C3C	0.8626 (4)	0.6592 (2)	0.25533 (10)	0.0275 (7)
H3C	0.9640	0.6283	0.2673	0.033*
C4C	0.7166 (4)	0.6985 (2)	0.28005 (10)	0.0276 (7)
C5C	0.5679 (4)	0.7451 (2)	0.26199 (10)	0.0295 (7)
H5C	0.4679	0.7726	0.2783	0.035*
C6C	0.5666 (4)	0.7510 (2)	0.22042 (11)	0.0305 (7)
H6C	0.4657	0.7827	0.2084	0.037*
C7C	0.7213 (4)	0.6901 (2)	0.32472 (10)	0.0285 (7)
C11C	0.8393 (4)	0.6737 (2)	0.12826 (10)	0.0312 (7)
H11G	0.8638	0.6047	0.1335	0.037*
H11H	0.9440	0.6980	0.1325	0.037*
C12C	0.7874 (4)	0.6941 (3)	0.08519 (10)	0.0333 (7)
H12G	0.7562	0.7634	0.0810	0.040*
H12H	0.6847	0.6677	0.0812	0.040*
C13C	0.9333 (4)	0.6513 (2)	0.05389 (11)	0.0340 (8)
H13G	1.0341	0.6797	0.0573	0.041*
H13H	0.9678	0.5825	0.0591	0.041*
C14C	0.8838 (4)	0.6666 (3)	0.01034 (11)	0.0341 (8)
H14G	0.7885	0.6341	0.0064	0.041*
H14H	0.8408	0.7350	0.0058	0.041*
C15C	1.0321 (5)	0.6305 (3)	−0.02104 (11)	0.0359 (8)
H15G	1.1279	0.6626	−0.0171	0.043*
H15H	1.0743	0.5619	−0.0169	0.043*
C16C	0.9792 (6)	0.6477 (3)	−0.06422 (12)	0.0495 (10)
H16J	1.0776	0.6226	−0.0830	0.074*
H16K	0.9413	0.7158	−0.0689	0.074*
H16L	0.8848	0.6158	−0.0684	0.074*
O1D	0.7245 (3)	0.17412 (18)	−0.06727 (7)	0.0346 (6)
O2D	0.8757 (3)	0.12829 (19)	0.11821 (7)	0.0390 (6)
H2D	0.8619	0.1313	0.1434	0.047*
O3D	0.6164 (3)	0.22701 (17)	0.12342 (7)	0.0353 (6)
C1D	0.7402 (4)	0.1709 (2)	−0.02651 (10)	0.0274 (7)
C2D	0.8876 (4)	0.1264 (2)	−0.00770 (10)	0.0286 (7)
H2K	0.9873	0.0949	−0.0231	0.034*
C3D	0.8855 (4)	0.1291 (2)	0.03441 (10)	0.0279 (7)
H3D	0.9850	0.0987	0.0472	0.033*
C4D	0.7414 (4)	0.1751 (2)	0.05791 (10)	0.0266 (7)
C5D	0.5945 (4)	0.2197 (2)	0.03863 (10)	0.0298 (7)
H5D	0.4955	0.2518	0.0541	0.036*
C6D	0.5940 (4)	0.2171 (3)	−0.00303 (11)	0.0331 (8)
H6D	0.4938	0.2468	−0.0158	0.040*
C7D	0.7384 (4)	0.1796 (2)	0.10228 (10)	0.0271 (7)
C11D	0.8690 (4)	0.1301 (2)	−0.09369 (9)	0.0282 (7)
H11I	0.8960	0.0609	−0.0890	0.034*
H11J	0.9717	0.1556	−0.0889	0.034*
C12D	0.8181 (4)	0.1519 (2)	−0.13653 (10)	0.0292 (7)
H12I	0.7829	0.2212	−0.1399	0.035*
H12J	0.7176	0.1240	−0.1410	0.035*
C13D	0.9638 (4)	0.1137 (2)	−0.16843 (10)	0.0272 (7)
H13I	1.0629	0.1433	−0.1646	0.033*
H13J	1.0017	0.0447	−0.1645	0.033*
C14D	0.9112 (4)	0.1326 (2)	−0.21152 (10)	0.0280 (7)
H14I	0.8178	0.0990	−0.2158	0.034*
H14J	0.8642	0.2011	−0.2147	0.034*
C15D	1.0560 (4)	0.1025 (2)	−0.24387 (10)	0.0312 (7)
H15I	1.1005	0.0335	−0.2415	0.037*
H15J	1.1510	0.1346	−0.2392	0.037*
C16D	1.0001 (5)	0.1253 (3)	−0.28689 (12)	0.0442 (9)
H16M	1.0981	0.1035	−0.3063	0.066*
H16N	0.9600	0.1937	−0.2898	0.066*
H16O	0.9068	0.0932	−0.2919	0.066*
O1E	0.7565 (3)	0.20931 (17)	0.38790 (7)	0.0331 (5)
O2E	0.6046 (3)	0.23770 (18)	0.20349 (7)	0.0366 (6)
H2E	0.6125	0.2299	0.1785	0.044*
O3E	0.8643 (3)	0.14043 (18)	0.19740 (7)	0.0371 (6)
C1E	0.7642 (4)	0.2003 (2)	0.34694 (10)	0.0273 (7)
C2E	0.9068 (4)	0.1525 (2)	0.32319 (10)	0.0269 (7)
H2L	1.0085	0.1224	0.3353	0.032*
C3E	0.8983 (4)	0.1494 (2)	0.28151 (10)	0.0274 (7)
H3E	0.9950	0.1171	0.2654	0.033*
C4E	0.7489 (4)	0.1934 (2)	0.26331 (10)	0.0250 (6)
C5E	0.6067 (4)	0.2406 (2)	0.28766 (10)	0.0270 (7)
H5E	0.5047	0.2704	0.2756	0.032*
C6E	0.6130 (4)	0.2441 (2)	0.32889 (10)	0.0283 (7)
H6E	0.5158	0.2760	0.3450	0.034*
C7E	0.7431 (4)	0.1887 (2)	0.21885 (10)	0.0268 (7)
C11E	0.9008 (4)	0.1635 (2)	0.41035 (10)	0.0299 (7)
H11K	1.0035	0.1901	0.4026	0.036*
H11L	0.9292	0.0947	0.4051	0.036*
C12E	0.8444 (4)	0.1825 (3)	0.45420 (10)	0.0327 (7)
H12K	0.7435	0.1539	0.4613	0.039*
H12L	0.8076	0.2516	0.4581	0.039*
C13E	0.9848 (4)	0.1436 (2)	0.48308 (10)	0.0315 (7)
H13K	1.0228	0.0744	0.4793	0.038*
H13L	1.0854	0.1729	0.4766	0.038*
C14E	0.9191 (5)	0.1638 (3)	0.52681 (11)	0.0403 (9)
H14K	0.8151	0.1371	0.5326	0.048*
H14L	0.8852	0.2331	0.5305	0.048*
C15E	1.0509 (6)	0.1232 (3)	0.55702 (11)	0.0448 (10)
H15K	1.1531	0.1517	0.5518	0.054*
H15L	1.0882	0.0543	0.5526	0.054*
C16E	0.9835 (8)	0.1401 (4)	0.60115 (13)	0.0666 (14)
H16P	1.0739	0.1115	0.6187	0.100*
H16Q	0.8832	0.1113	0.6067	0.100*
H16R	0.9504	0.2082	0.6062	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0306 (12)	0.0450 (14)	0.0266 (13)	0.0017 (10)	−0.0031 (10)	−0.0015 (10)
O2	0.0339 (13)	0.0473 (15)	0.0284 (13)	−0.0038 (11)	−0.0009 (10)	−0.0007 (11)
O3	0.0301 (12)	0.0501 (16)	0.0355 (14)	−0.0055 (11)	−0.0058 (11)	−0.0016 (12)
C1	0.0281 (16)	0.0310 (17)	0.0300 (18)	−0.0092 (13)	−0.0008 (13)	−0.0064 (14)
C2	0.0267 (16)	0.0331 (18)	0.0319 (18)	−0.0030 (14)	−0.0053 (14)	0.0020 (14)
C3	0.0247 (15)	0.0364 (18)	0.0302 (18)	−0.0046 (14)	−0.0004 (13)	−0.0069 (14)
C4	0.0271 (16)	0.0312 (17)	0.0321 (18)	−0.0111 (13)	−0.0008 (13)	−0.0022 (14)
C5	0.0280 (16)	0.0329 (18)	0.0342 (19)	−0.0037 (14)	−0.0070 (14)	0.0021 (14)
C6	0.0268 (16)	0.0373 (19)	0.0298 (18)	0.0004 (14)	−0.0026 (13)	−0.0010 (14)
C7	0.0284 (16)	0.0363 (18)	0.0306 (18)	−0.0116 (14)	−0.0034 (14)	−0.0016 (14)
C11	0.0271 (16)	0.0326 (18)	0.0327 (19)	−0.0040 (14)	−0.0031 (14)	−0.0049 (14)
C12	0.0325 (17)	0.0364 (19)	0.0285 (18)	−0.0088 (14)	−0.0020 (14)	−0.0045 (14)
C13	0.0395 (19)	0.0355 (19)	0.033 (2)	−0.0069 (15)	−0.0072 (15)	−0.0018 (15)
C14	0.046 (2)	0.054 (2)	0.0283 (19)	−0.0120 (18)	−0.0022 (16)	0.0022 (17)
C15	0.069 (3)	0.061 (3)	0.031 (2)	−0.006 (2)	−0.009 (2)	0.0002 (19)
C16	0.093 (4)	0.090 (4)	0.029 (2)	−0.012 (3)	−0.004 (2)	0.002 (2)
O1A	0.0295 (12)	0.0453 (15)	0.0302 (13)	−0.0001 (10)	−0.0014 (10)	−0.0057 (11)
O2A	0.0310 (12)	0.0482 (15)	0.0329 (14)	−0.0040 (11)	−0.0063 (10)	0.0007 (12)
O3A	0.0324 (13)	0.0516 (16)	0.0325 (14)	−0.0049 (11)	0.0012 (11)	−0.0014 (12)
C1A	0.0276 (16)	0.0350 (18)	0.0277 (18)	−0.0107 (14)	−0.0037 (13)	−0.0021 (14)
C2A	0.0290 (17)	0.0329 (18)	0.038 (2)	−0.0029 (14)	0.0001 (14)	−0.0096 (15)
C3A	0.0276 (16)	0.0301 (18)	0.041 (2)	−0.0029 (14)	−0.0060 (15)	−0.0020 (15)
C4A	0.0246 (15)	0.0347 (18)	0.0333 (19)	−0.0124 (14)	−0.0021 (13)	−0.0016 (14)
C5A	0.0266 (16)	0.044 (2)	0.0295 (18)	−0.0059 (15)	0.0048 (14)	−0.0053 (15)
C6A	0.0242 (16)	0.043 (2)	0.036 (2)	0.0004 (14)	−0.0014 (14)	−0.0020 (16)
C7A	0.0265 (16)	0.0347 (18)	0.0339 (19)	−0.0112 (14)	−0.0014 (14)	0.0007 (14)
C11A	0.0301 (17)	0.0391 (19)	0.0307 (19)	−0.0061 (14)	0.0000 (14)	−0.0067 (15)
C12A	0.0369 (18)	0.0351 (19)	0.0308 (19)	−0.0072 (15)	−0.0050 (15)	0.0025 (14)
C13A	0.046 (2)	0.0348 (19)	0.0303 (19)	−0.0040 (16)	−0.0037 (16)	−0.0017 (15)
C14A	0.049 (2)	0.044 (2)	0.032 (2)	−0.0089 (18)	−0.0035 (17)	0.0019 (16)
C15A	0.071 (3)	0.051 (3)	0.034 (2)	−0.008 (2)	−0.001 (2)	−0.0022 (18)
C16A	0.091 (4)	0.081 (4)	0.029 (2)	−0.015 (3)	−0.007 (2)	0.001 (2)
O1B	0.0279 (12)	0.0456 (14)	0.0270 (13)	0.0014 (10)	−0.0030 (10)	−0.0052 (11)
O2B	0.0382 (13)	0.0535 (16)	0.0266 (13)	−0.0042 (12)	0.0029 (11)	−0.0057 (12)
O3B	0.0334 (13)	0.0521 (16)	0.0303 (13)	−0.0060 (11)	−0.0044 (10)	−0.0042 (11)
C1B	0.0306 (16)	0.0306 (17)	0.0239 (16)	−0.0081 (13)	−0.0019 (13)	−0.0026 (13)
C2B	0.0254 (15)	0.0281 (17)	0.0326 (18)	−0.0043 (13)	−0.0005 (13)	0.0010 (13)
C3B	0.0282 (16)	0.0273 (16)	0.0282 (17)	−0.0074 (13)	0.0015 (13)	−0.0037 (13)
C4B	0.0267 (15)	0.0285 (17)	0.0298 (18)	−0.0093 (13)	−0.0006 (13)	−0.0031 (13)
C5B	0.0253 (16)	0.044 (2)	0.0291 (18)	−0.0063 (14)	−0.0016 (13)	−0.0022 (15)
C6B	0.0245 (16)	0.046 (2)	0.0290 (18)	−0.0022 (14)	0.0050 (13)	−0.0099 (15)
C7B	0.0279 (16)	0.0328 (18)	0.0305 (18)	−0.0119 (14)	0.0011 (14)	−0.0037 (14)
C11B	0.0274 (16)	0.0275 (16)	0.0302 (18)	−0.0028 (13)	−0.0043 (13)	0.0020 (13)
C12B	0.0288 (16)	0.0329 (17)	0.0261 (17)	−0.0069 (13)	−0.0009 (13)	−0.0031 (13)
C13B	0.0324 (16)	0.0264 (16)	0.0276 (17)	−0.0053 (13)	−0.0037 (13)	0.0000 (13)
C14B	0.0388 (19)	0.0374 (19)	0.0313 (19)	−0.0112 (15)	−0.0020 (15)	−0.0014 (15)
C15B	0.054 (2)	0.0320 (18)	0.0277 (19)	−0.0107 (16)	−0.0099 (16)	0.0023 (14)
C16B	0.081 (3)	0.062 (3)	0.023 (2)	−0.014 (2)	−0.006 (2)	−0.0007 (18)
O1C	0.0344 (12)	0.0395 (14)	0.0256 (13)	−0.0014 (10)	−0.0024 (10)	0.0008 (10)
O2C	0.0379 (13)	0.0438 (15)	0.0284 (13)	−0.0016 (11)	0.0013 (11)	−0.0053 (11)
O3C	0.0319 (12)	0.0476 (15)	0.0315 (14)	−0.0045 (11)	−0.0042 (10)	−0.0015 (11)
C1C	0.0317 (16)	0.0237 (16)	0.0275 (17)	−0.0086 (13)	−0.0030 (13)	−0.0015 (13)
C2C	0.0278 (16)	0.0297 (17)	0.0262 (17)	−0.0048 (13)	0.0003 (13)	−0.0032 (13)
C3C	0.0293 (16)	0.0258 (16)	0.0281 (17)	−0.0070 (13)	−0.0034 (13)	−0.0004 (13)
C4C	0.0288 (16)	0.0264 (16)	0.0303 (18)	−0.0126 (13)	0.0020 (13)	−0.0051 (13)
C5C	0.0267 (16)	0.0313 (17)	0.0304 (18)	−0.0070 (13)	0.0025 (13)	−0.0059 (14)
C6C	0.0251 (15)	0.0302 (17)	0.0357 (19)	−0.0040 (13)	−0.0044 (13)	−0.0016 (14)
C7C	0.0279 (16)	0.0313 (17)	0.0280 (17)	−0.0110 (14)	0.0006 (13)	−0.0042 (13)
C11C	0.0348 (17)	0.0304 (17)	0.0276 (18)	−0.0055 (14)	0.0008 (14)	−0.0038 (14)
C12C	0.0364 (18)	0.0354 (19)	0.0286 (18)	−0.0077 (15)	−0.0042 (14)	−0.0005 (14)
C13C	0.0357 (18)	0.0316 (18)	0.0332 (19)	−0.0041 (14)	0.0005 (15)	−0.0070 (14)
C14C	0.0335 (17)	0.0353 (19)	0.0331 (19)	−0.0065 (15)	−0.0005 (14)	−0.0031 (15)
C15C	0.0411 (19)	0.0371 (19)	0.0294 (19)	−0.0096 (16)	0.0024 (15)	−0.0009 (15)
C16C	0.060 (3)	0.061 (3)	0.028 (2)	−0.015 (2)	0.0014 (18)	−0.0039 (18)
O1D	0.0300 (12)	0.0494 (15)	0.0213 (12)	−0.0007 (11)	−0.0026 (9)	−0.0013 (10)
O2D	0.0392 (13)	0.0502 (15)	0.0241 (13)	0.0001 (11)	−0.0063 (10)	0.0016 (11)
O3D	0.0380 (13)	0.0396 (14)	0.0250 (12)	−0.0011 (11)	0.0020 (10)	−0.0058 (10)
C1D	0.0290 (16)	0.0330 (17)	0.0205 (16)	−0.0074 (13)	−0.0008 (13)	−0.0008 (13)
C2D	0.0264 (15)	0.0306 (17)	0.0277 (17)	−0.0038 (13)	0.0002 (13)	−0.0054 (13)
C3D	0.0292 (16)	0.0274 (16)	0.0272 (17)	−0.0042 (13)	−0.0085 (13)	0.0016 (13)
C4D	0.0275 (15)	0.0264 (16)	0.0265 (17)	−0.0075 (13)	0.0001 (13)	−0.0023 (13)
C5D	0.0257 (15)	0.0351 (18)	0.0263 (17)	−0.0018 (13)	−0.0004 (13)	−0.0005 (14)
C6D	0.0231 (15)	0.042 (2)	0.0326 (19)	−0.0030 (14)	−0.0026 (13)	−0.0029 (15)
C7D	0.0274 (16)	0.0262 (16)	0.0286 (17)	−0.0064 (13)	−0.0062 (13)	0.0006 (13)
C11D	0.0272 (15)	0.0373 (18)	0.0199 (16)	−0.0064 (14)	0.0008 (12)	−0.0040 (13)
C12D	0.0296 (16)	0.0351 (18)	0.0227 (17)	−0.0069 (14)	0.0011 (13)	−0.0019 (13)
C13D	0.0296 (16)	0.0277 (16)	0.0241 (17)	−0.0053 (13)	−0.0007 (13)	−0.0010 (13)
C14D	0.0267 (15)	0.0295 (17)	0.0283 (17)	−0.0064 (13)	−0.0030 (13)	0.0006 (13)
C15D	0.0323 (17)	0.0336 (18)	0.0277 (18)	−0.0080 (14)	0.0022 (14)	−0.0052 (14)
C16D	0.049 (2)	0.054 (2)	0.032 (2)	−0.0163 (19)	−0.0008 (17)	−0.0026 (17)
O1E	0.0307 (12)	0.0436 (14)	0.0211 (12)	0.0021 (10)	−0.0031 (9)	−0.0046 (10)
O2E	0.0352 (13)	0.0464 (15)	0.0248 (13)	0.0008 (11)	−0.0044 (10)	−0.0062 (11)
O3E	0.0359 (13)	0.0466 (15)	0.0243 (12)	0.0014 (11)	0.0006 (10)	−0.0038 (11)
C1E	0.0303 (16)	0.0304 (17)	0.0225 (16)	−0.0095 (13)	0.0002 (13)	−0.0039 (13)
C2E	0.0241 (15)	0.0274 (16)	0.0282 (17)	−0.0025 (13)	−0.0028 (13)	0.0002 (13)
C3E	0.0250 (15)	0.0255 (16)	0.0308 (18)	−0.0036 (13)	0.0014 (13)	−0.0047 (13)
C4E	0.0279 (15)	0.0224 (15)	0.0263 (17)	−0.0093 (12)	−0.0011 (13)	−0.0019 (12)
C5E	0.0246 (15)	0.0294 (17)	0.0274 (17)	−0.0063 (13)	−0.0025 (13)	−0.0014 (13)
C6E	0.0240 (15)	0.0303 (17)	0.0291 (17)	−0.0028 (13)	0.0006 (13)	−0.0020 (13)
C7E	0.0259 (15)	0.0233 (15)	0.0315 (18)	−0.0056 (13)	−0.0014 (13)	−0.0017 (13)
C11E	0.0273 (16)	0.0368 (19)	0.0247 (17)	−0.0041 (14)	−0.0033 (13)	−0.0019 (14)
C12E	0.0300 (17)	0.0408 (19)	0.0270 (18)	−0.0062 (14)	−0.0031 (14)	−0.0012 (14)
C13E	0.0387 (18)	0.0321 (18)	0.0258 (17)	−0.0099 (14)	−0.0088 (14)	0.0025 (14)
C14E	0.051 (2)	0.045 (2)	0.0289 (19)	−0.0170 (18)	−0.0084 (16)	0.0030 (16)
C15E	0.072 (3)	0.034 (2)	0.031 (2)	−0.0131 (19)	−0.0186 (19)	0.0041 (15)
C16E	0.106 (4)	0.066 (3)	0.027 (2)	−0.013 (3)	−0.019 (2)	0.006 (2)

Geometric parameters (Å, º)

O1—C1	1.371 (4)	O1C—C1C	1.383 (4)
O1—C11	1.442 (4)	O1C—C11C	1.450 (4)
O2—C7	1.306 (4)	O2C—C7C	1.306 (4)
O2—H2	0.8400	O2C—H2C	0.8400
O3—C7	1.259 (4)	O3C—C7C	1.253 (4)
C1—C2	1.400 (5)	C1C—C2C	1.395 (5)
C1—C6	1.408 (5)	C1C—C6C	1.407 (5)
C2—C3	1.408 (5)	C2C—C3C	1.399 (5)
C2—H2F	0.9500	C2C—H2I	0.9500
C3—C4	1.391 (5)	C3C—C4C	1.400 (4)
C3—H3	0.9500	C3C—H3C	0.9500
C4—C5	1.402 (5)	C4C—C5C	1.407 (5)
C4—C7	1.484 (5)	C4C—C7C	1.496 (5)
C5—C6	1.390 (5)	C5C—C6C	1.390 (5)
C5—H5	0.9500	C5C—H5C	0.9500
C6—H6	0.9500	C6C—H6C	0.9500
C11—C12	1.531 (5)	C11C—C12C	1.531 (5)
C11—H11A	0.9900	C11C—H11G	0.9900
C11—H11B	0.9900	C11C—H11H	0.9900
C12—C13	1.522 (5)	C12C—C13C	1.542 (5)
C12—H12A	0.9900	C12C—H12G	0.9900
C12—H12B	0.9900	C12C—H12H	0.9900
C13—C14	1.537 (5)	C13C—C14C	1.534 (5)
C13—H13A	0.9900	C13C—H13G	0.9900
C13—H13B	0.9900	C13C—H13H	0.9900
C14—C15	1.529 (6)	C14C—C15C	1.533 (5)
C14—H14A	0.9900	C14C—H14G	0.9900
C14—H14B	0.9900	C14C—H14H	0.9900
C15—C16	1.516 (6)	C15C—C16C	1.532 (5)
C15—H15A	0.9900	C15C—H15G	0.9900
C15—H15B	0.9900	C15C—H15H	0.9900
C16—H16A	0.9800	C16C—H16J	0.9800
C16—H16B	0.9800	C16C—H16K	0.9800
C16—H16C	0.9800	C16C—H16L	0.9800
O1A—C1A	1.382 (4)	O1D—C1D	1.375 (4)
O1A—C11A	1.442 (4)	O1D—C11D	1.442 (4)
O2A—C7A	1.305 (4)	O2D—C7D	1.327 (4)
O2A—H2A	0.8400	O2D—H2D	0.8400
O3A—C7A	1.261 (4)	O3D—C7D	1.247 (4)
C1A—C2A	1.391 (5)	C1D—C2D	1.402 (5)
C1A—C6A	1.408 (5)	C1D—C6D	1.408 (4)
C2A—C3A	1.399 (5)	C2D—C3D	1.406 (5)
C2A—H2G	0.9500	C2D—H2K	0.9500
C3A—C4A	1.397 (5)	C3D—C4D	1.396 (4)
C3A—H3A	0.9500	C3D—H3D	0.9500
C4A—C5A	1.386 (5)	C4D—C5D	1.407 (4)
C4A—C7A	1.491 (5)	C4D—C7D	1.483 (4)
C5A—C6A	1.389 (5)	C5D—C6D	1.393 (5)
C5A—H5A	0.9500	C5D—H5D	0.9500
C6A—H6A	0.9500	C6D—H6D	0.9500
C11A—C12A	1.523 (5)	C11D—C12D	1.524 (4)
C11A—H11C	0.9900	C11D—H11I	0.9900
C11A—H11D	0.9900	C11D—H11J	0.9900
C12A—C13A	1.517 (5)	C12D—C13D	1.538 (4)
C12A—H12C	0.9900	C12D—H12I	0.9900
C12A—H12D	0.9900	C12D—H12J	0.9900
C13A—C14A	1.535 (5)	C13D—C14D	1.531 (4)
C13A—H13C	0.9900	C13D—H13I	0.9900
C13A—H13D	0.9900	C13D—H13J	0.9900
C14A—C15A	1.530 (6)	C14D—C15D	1.522 (4)
C14A—H14C	0.9900	C14D—H14I	0.9900
C14A—H14D	0.9900	C14D—H14J	0.9900
C15A—C16A	1.529 (6)	C15D—C16D	1.544 (5)
C15A—H15C	0.9900	C15D—H15I	0.9900
C15A—H15D	0.9900	C15D—H15J	0.9900
C16A—H16D	0.9800	C16D—H16M	0.9800
C16A—H16E	0.9800	C16D—H16N	0.9800
C16A—H16F	0.9800	C16D—H16O	0.9800
O1B—C1B	1.368 (4)	O1E—C1E	1.372 (4)
O1B—C11B	1.451 (4)	O1E—C11E	1.453 (4)
O2B—C7B	1.305 (4)	O2E—C7E	1.314 (4)
O2B—H2B	0.8400	O2E—H2E	0.8400
O3B—C7B	1.244 (4)	O3E—C7E	1.254 (4)
C1B—C2B	1.409 (4)	C1E—C2E	1.401 (4)
C1B—C6B	1.409 (5)	C1E—C6E	1.411 (5)
C2B—C3B	1.396 (5)	C2E—C3E	1.400 (5)
C2B—H2H	0.9500	C2E—H2L	0.9500
C3B—C4B	1.400 (5)	C3E—C4E	1.403 (4)
C3B—H3B	0.9500	C3E—H3E	0.9500
C4B—C5B	1.404 (5)	C4E—C5E	1.406 (4)
C4B—C7B	1.494 (5)	C4E—C7E	1.492 (4)
C5B—C6B	1.381 (5)	C5E—C6E	1.384 (5)
C5B—H5B	0.9500	C5E—H5E	0.9500
C6B—H6B	0.9500	C6E—H6E	0.9500
C11B—C12B	1.514 (5)	C11E—C12E	1.513 (5)
C11B—H11E	0.9900	C11E—H11K	0.9900
C11B—H11F	0.9900	C11E—H11L	0.9900
C12B—C13B	1.539 (4)	C12E—C13E	1.540 (5)
C12B—H12E	0.9900	C12E—H12K	0.9900
C12B—H12F	0.9900	C12E—H12L	0.9900
C13B—C14B	1.531 (5)	C13E—C14E	1.528 (5)
C13B—H13E	0.9900	C13E—H13K	0.9900
C13B—H13F	0.9900	C13E—H13L	0.9900
C14B—C15B	1.534 (5)	C14E—C15E	1.529 (5)
C14B—H14E	0.9900	C14E—H14K	0.9900
C14B—H14F	0.9900	C14E—H14L	0.9900
C15B—C16B	1.514 (5)	C15E—C16E	1.537 (6)
C15B—H15E	0.9900	C15E—H15K	0.9900
C15B—H15F	0.9900	C15E—H15L	0.9900
C16B—H16G	0.9800	C16E—H16P	0.9800
C16B—H16H	0.9800	C16E—H16Q	0.9800
C16B—H16I	0.9800	C16E—H16R	0.9800
C1—O1—C11	118.4 (3)	C1C—O1C—C11C	117.8 (2)
C7—O2—H2	109.5	C7C—O2C—H2C	109.5
O1—C1—C2	125.1 (3)	O1C—C1C—C2C	124.8 (3)
O1—C1—C6	115.4 (3)	O1C—C1C—C6C	115.3 (3)
C2—C1—C6	119.5 (3)	C2C—C1C—C6C	119.9 (3)
C1—C2—C3	119.2 (3)	C1C—C2C—C3C	119.2 (3)
C1—C2—H2F	120.4	C1C—C2C—H2I	120.4
C3—C2—H2F	120.4	C3C—C2C—H2I	120.4
C4—C3—C2	121.6 (3)	C2C—C3C—C4C	121.5 (3)
C4—C3—H3	119.2	C2C—C3C—H3C	119.2
C2—C3—H3	119.2	C4C—C3C—H3C	119.2
C3—C4—C5	118.6 (3)	C3C—C4C—C5C	118.7 (3)
C3—C4—C7	122.4 (3)	C3C—C4C—C7C	119.9 (3)
C5—C4—C7	119.0 (3)	C5C—C4C—C7C	121.5 (3)
C6—C5—C4	120.8 (3)	C6C—C5C—C4C	120.3 (3)
C6—C5—H5	119.6	C6C—C5C—H5C	119.9
C4—C5—H5	119.6	C4C—C5C—H5C	119.9
C5—C6—C1	120.3 (3)	C5C—C6C—C1C	120.5 (3)
C5—C6—H6	119.8	C5C—C6C—H6C	119.8
C1—C6—H6	119.8	C1C—C6C—H6C	119.8
O3—C7—O2	123.1 (3)	O3C—C7C—O2C	122.9 (3)
O3—C7—C4	120.1 (3)	O3C—C7C—C4C	120.6 (3)
O2—C7—C4	116.8 (3)	O2C—C7C—C4C	116.5 (3)
O1—C11—C12	107.5 (3)	O1C—C11C—C12C	107.5 (3)
O1—C11—H11A	110.2	O1C—C11C—H11G	110.2
C12—C11—H11A	110.2	C12C—C11C—H11G	110.2
O1—C11—H11B	110.2	O1C—C11C—H11H	110.2
C12—C11—H11B	110.2	C12C—C11C—H11H	110.2
H11A—C11—H11B	108.5	H11G—C11C—H11H	108.5
C13—C12—C11	111.5 (3)	C11C—C12C—C13C	112.0 (3)
C13—C12—H12A	109.3	C11C—C12C—H12G	109.2
C11—C12—H12A	109.3	C13C—C12C—H12G	109.2
C13—C12—H12B	109.3	C11C—C12C—H12H	109.2
C11—C12—H12B	109.3	C13C—C12C—H12H	109.2
H12A—C12—H12B	108.0	H12G—C12C—H12H	107.9
C12—C13—C14	113.0 (3)	C14C—C13C—C12C	113.6 (3)
C12—C13—H13A	109.0	C14C—C13C—H13G	108.8
C14—C13—H13A	109.0	C12C—C13C—H13G	108.8
C12—C13—H13B	109.0	C14C—C13C—H13H	108.8
C14—C13—H13B	109.0	C12C—C13C—H13H	108.8
H13A—C13—H13B	107.8	H13G—C13C—H13H	107.7
C15—C14—C13	112.9 (3)	C15C—C14C—C13C	113.9 (3)
C15—C14—H14A	109.0	C15C—C14C—H14G	108.8
C13—C14—H14A	109.0	C13C—C14C—H14G	108.8
C15—C14—H14B	109.0	C15C—C14C—H14H	108.8
C13—C14—H14B	109.0	C13C—C14C—H14H	108.8
H14A—C14—H14B	107.8	H14G—C14C—H14H	107.7
C16—C15—C14	114.5 (4)	C16C—C15C—C14C	112.7 (3)
C16—C15—H15A	108.6	C16C—C15C—H15G	109.0
C14—C15—H15A	108.6	C14C—C15C—H15G	109.0
C16—C15—H15B	108.6	C16C—C15C—H15H	109.0
C14—C15—H15B	108.6	C14C—C15C—H15H	109.0
H15A—C15—H15B	107.6	H15G—C15C—H15H	107.8
C15—C16—H16A	109.5	C15C—C16C—H16J	109.5
C15—C16—H16B	109.5	C15C—C16C—H16K	109.5
H16A—C16—H16B	109.5	H16J—C16C—H16K	109.5
C15—C16—H16C	109.5	C15C—C16C—H16L	109.5
H16A—C16—H16C	109.5	H16J—C16C—H16L	109.5
H16B—C16—H16C	109.5	H16K—C16C—H16L	109.5
C1A—O1A—C11A	118.2 (3)	C1D—O1D—C11D	119.1 (2)
C7A—O2A—H2A	109.5	C7D—O2D—H2D	109.5
O1A—C1A—C2A	124.9 (3)	O1D—C1D—C2D	125.1 (3)
O1A—C1A—C6A	115.9 (3)	O1D—C1D—C6D	115.3 (3)
C2A—C1A—C6A	119.3 (3)	C2D—C1D—C6D	119.6 (3)
C1A—C2A—C3A	119.9 (3)	C1D—C2D—C3D	118.9 (3)
C1A—C2A—H2G	120.0	C1D—C2D—H2K	120.6
C3A—C2A—H2G	120.0	C3D—C2D—H2K	120.6
C4A—C3A—C2A	120.7 (3)	C4D—C3D—C2D	121.9 (3)
C4A—C3A—H3A	119.7	C4D—C3D—H3D	119.0
C2A—C3A—H3A	119.7	C2D—C3D—H3D	119.0
C5A—C4A—C3A	119.2 (3)	C3D—C4D—C5D	118.6 (3)
C5A—C4A—C7A	118.9 (3)	C3D—C4D—C7D	122.4 (3)
C3A—C4A—C7A	121.9 (3)	C5D—C4D—C7D	118.9 (3)
C4A—C5A—C6A	120.7 (3)	C6D—C5D—C4D	120.2 (3)
C4A—C5A—H5A	119.6	C6D—C5D—H5D	119.9
C6A—C5A—H5A	119.6	C4D—C5D—H5D	119.9
C5A—C6A—C1A	120.2 (3)	C5D—C6D—C1D	120.8 (3)
C5A—C6A—H6A	119.9	C5D—C6D—H6D	119.6
C1A—C6A—H6A	119.9	C1D—C6D—H6D	119.6
O3A—C7A—O2A	122.7 (3)	O3D—C7D—O2D	121.9 (3)
O3A—C7A—C4A	120.6 (3)	O3D—C7D—C4D	123.2 (3)
O2A—C7A—C4A	116.7 (3)	O2D—C7D—C4D	114.9 (3)
O1A—C11A—C12A	108.7 (3)	O1D—C11D—C12D	107.0 (3)
O1A—C11A—H11C	109.9	O1D—C11D—H11I	110.3
C12A—C11A—H11C	109.9	C12D—C11D—H11I	110.3
O1A—C11A—H11D	109.9	O1D—C11D—H11J	110.3
C12A—C11A—H11D	109.9	C12D—C11D—H11J	110.3
H11C—C11A—H11D	108.3	H11I—C11D—H11J	108.6
C13A—C12A—C11A	111.7 (3)	C11D—C12D—C13D	113.1 (3)
C13A—C12A—H12C	109.3	C11D—C12D—H12I	109.0
C11A—C12A—H12C	109.3	C13D—C12D—H12I	109.0
C13A—C12A—H12D	109.3	C11D—C12D—H12J	109.0
C11A—C12A—H12D	109.3	C13D—C12D—H12J	109.0
H12C—C12A—H12D	107.9	H12I—C12D—H12J	107.8
C12A—C13A—C14A	114.4 (3)	C14D—C13D—C12D	113.3 (3)
C12A—C13A—H13C	108.7	C14D—C13D—H13I	108.9
C14A—C13A—H13C	108.7	C12D—C13D—H13I	108.9
C12A—C13A—H13D	108.7	C14D—C13D—H13J	108.9
C14A—C13A—H13D	108.7	C12D—C13D—H13J	108.9
H13C—C13A—H13D	107.6	H13I—C13D—H13J	107.7
C15A—C14A—C13A	113.2 (3)	C15D—C14D—C13D	114.7 (3)
C15A—C14A—H14C	108.9	C15D—C14D—H14I	108.6
C13A—C14A—H14C	108.9	C13D—C14D—H14I	108.6
C15A—C14A—H14D	108.9	C15D—C14D—H14J	108.6
C13A—C14A—H14D	108.9	C13D—C14D—H14J	108.6
H14C—C14A—H14D	107.8	H14I—C14D—H14J	107.6
C16A—C15A—C14A	113.7 (4)	C14D—C15D—C16D	113.4 (3)
C16A—C15A—H15C	108.8	C14D—C15D—H15I	108.9
C14A—C15A—H15C	108.8	C16D—C15D—H15I	108.9
C16A—C15A—H15D	108.8	C14D—C15D—H15J	108.9
C14A—C15A—H15D	108.8	C16D—C15D—H15J	108.9
H15C—C15A—H15D	107.7	H15I—C15D—H15J	107.7
C15A—C16A—H16D	109.5	C15D—C16D—H16M	109.5
C15A—C16A—H16E	109.5	C15D—C16D—H16N	109.5
H16D—C16A—H16E	109.5	H16M—C16D—H16N	109.5
C15A—C16A—H16F	109.5	C15D—C16D—H16O	109.5
H16D—C16A—H16F	109.5	H16M—C16D—H16O	109.5
H16E—C16A—H16F	109.5	H16N—C16D—H16O	109.5
C1B—O1B—C11B	120.2 (2)	C1E—O1E—C11E	120.2 (2)
C7B—O2B—H2B	109.5	C7E—O2E—H2E	109.5
O1B—C1B—C2B	126.0 (3)	O1E—C1E—C2E	125.3 (3)
O1B—C1B—C6B	114.4 (3)	O1E—C1E—C6E	114.7 (3)
C2B—C1B—C6B	119.6 (3)	C2E—C1E—C6E	120.0 (3)
C3B—C2B—C1B	119.3 (3)	C3E—C2E—C1E	119.5 (3)
C3B—C2B—H2H	120.3	C3E—C2E—H2L	120.3
C1B—C2B—H2H	120.3	C1E—C2E—H2L	120.3
C2B—C3B—C4B	121.3 (3)	C2E—C3E—C4E	120.8 (3)
C2B—C3B—H3B	119.4	C2E—C3E—H3E	119.6
C4B—C3B—H3B	119.4	C4E—C3E—H3E	119.6
C3B—C4B—C5B	118.6 (3)	C3E—C4E—C5E	118.9 (3)
C3B—C4B—C7B	122.1 (3)	C3E—C4E—C7E	119.7 (3)
C5B—C4B—C7B	119.3 (3)	C5E—C4E—C7E	121.4 (3)
C6B—C5B—C4B	121.1 (3)	C6E—C5E—C4E	121.0 (3)
C6B—C5B—H5B	119.5	C6E—C5E—H5E	119.5
C4B—C5B—H5B	119.5	C4E—C5E—H5E	119.5
C5B—C6B—C1B	120.1 (3)	C5E—C6E—C1E	119.8 (3)
C5B—C6B—H6B	119.9	C5E—C6E—H6E	120.1
C1B—C6B—H6B	119.9	C1E—C6E—H6E	120.1
O3B—C7B—O2B	123.2 (3)	O3E—C7E—O2E	122.0 (3)
O3B—C7B—C4B	121.0 (3)	O3E—C7E—C4E	121.6 (3)
O2B—C7B—C4B	115.8 (3)	O2E—C7E—C4E	116.4 (3)
O1B—C11B—C12B	105.6 (3)	O1E—C11E—C12E	106.1 (3)
O1B—C11B—H11E	110.6	O1E—C11E—H11K	110.5
C12B—C11B—H11E	110.6	C12E—C11E—H11K	110.5
O1B—C11B—H11F	110.6	O1E—C11E—H11L	110.5
C12B—C11B—H11F	110.6	C12E—C11E—H11L	110.5
H11E—C11B—H11F	108.7	H11K—C11E—H11L	108.7
C11B—C12B—C13B	114.7 (3)	C11E—C12E—C13E	114.0 (3)
C11B—C12B—H12E	108.6	C11E—C12E—H12K	108.8
C13B—C12B—H12E	108.6	C13E—C12E—H12K	108.8
C11B—C12B—H12F	108.6	C11E—C12E—H12L	108.8
C13B—C12B—H12F	108.6	C13E—C12E—H12L	108.8
H12E—C12B—H12F	107.6	H12K—C12E—H12L	107.6
C14B—C13B—C12B	112.4 (3)	C14E—C13E—C12E	111.4 (3)
C14B—C13B—H13E	109.1	C14E—C13E—H13K	109.3
C12B—C13B—H13E	109.1	C12E—C13E—H13K	109.3
C14B—C13B—H13F	109.1	C14E—C13E—H13L	109.3
C12B—C13B—H13F	109.1	C12E—C13E—H13L	109.3
H13E—C13B—H13F	107.9	H13K—C13E—H13L	108.0
C13B—C14B—C15B	114.2 (3)	C13E—C14E—C15E	113.7 (3)
C13B—C14B—H14E	108.7	C13E—C14E—H14K	108.8
C15B—C14B—H14E	108.7	C15E—C14E—H14K	108.8
C13B—C14B—H14F	108.7	C13E—C14E—H14L	108.8
C15B—C14B—H14F	108.7	C15E—C14E—H14L	108.8
H14E—C14B—H14F	107.6	H14K—C14E—H14L	107.7
C16B—C15B—C14B	114.4 (3)	C14E—C15E—C16E	114.1 (4)
C16B—C15B—H15E	108.6	C14E—C15E—H15K	108.7
C14B—C15B—H15E	108.6	C16E—C15E—H15K	108.7
C16B—C15B—H15F	108.6	C14E—C15E—H15L	108.7
C14B—C15B—H15F	108.6	C16E—C15E—H15L	108.7
H15E—C15B—H15F	107.6	H15K—C15E—H15L	107.6
C15B—C16B—H16G	109.5	C15E—C16E—H16P	109.5
C15B—C16B—H16H	109.5	C15E—C16E—H16Q	109.5
H16G—C16B—H16H	109.5	H16P—C16E—H16Q	109.5
C15B—C16B—H16I	109.5	C15E—C16E—H16R	109.5
H16G—C16B—H16I	109.5	H16P—C16E—H16R	109.5
H16H—C16B—H16I	109.5	H16Q—C16E—H16R	109.5
C11—O1—C1—C2	−0.1 (5)	C11C—O1C—C1C—C2C	5.2 (4)
C11—O1—C1—C6	−179.4 (3)	C11C—O1C—C1C—C6C	−175.1 (3)
O1—C1—C2—C3	−177.8 (3)	O1C—C1C—C2C—C3C	179.9 (3)
C6—C1—C2—C3	1.5 (5)	C6C—C1C—C2C—C3C	0.3 (5)
C1—C2—C3—C4	−0.1 (5)	C1C—C2C—C3C—C4C	0.3 (5)
C2—C3—C4—C5	−1.1 (5)	C2C—C3C—C4C—C5C	−0.7 (5)
C2—C3—C4—C7	177.8 (3)	C2C—C3C—C4C—C7C	179.1 (3)
C3—C4—C5—C6	0.9 (5)	C3C—C4C—C5C—C6C	0.5 (5)
C7—C4—C5—C6	−178.0 (3)	C7C—C4C—C5C—C6C	−179.3 (3)
C4—C5—C6—C1	0.4 (5)	C4C—C5C—C6C—C1C	0.1 (5)
O1—C1—C6—C5	177.7 (3)	O1C—C1C—C6C—C5C	179.8 (3)
C2—C1—C6—C5	−1.6 (5)	C2C—C1C—C6C—C5C	−0.5 (5)
C3—C4—C7—O3	−175.3 (3)	C3C—C4C—C7C—O3C	−7.4 (5)
C5—C4—C7—O3	3.6 (5)	C5C—C4C—C7C—O3C	172.5 (3)
C3—C4—C7—O2	5.0 (5)	C3C—C4C—C7C—O2C	172.5 (3)
C5—C4—C7—O2	−176.2 (3)	C5C—C4C—C7C—O2C	−7.7 (4)
C1—O1—C11—C12	178.1 (3)	C1C—O1C—C11C—C12C	178.8 (3)
O1—C11—C12—C13	176.3 (3)	O1C—C11C—C12C—C13C	177.4 (3)
C11—C12—C13—C14	179.8 (3)	C11C—C12C—C13C—C14C	177.6 (3)
C12—C13—C14—C15	180.0 (3)	C12C—C13C—C14C—C15C	175.8 (3)
C13—C14—C15—C16	177.0 (4)	C13C—C14C—C15C—C16C	−179.4 (3)
C11A—O1A—C1A—C2A	−0.1 (5)	C11D—O1D—C1D—C2D	−0.8 (5)
C11A—O1A—C1A—C6A	−179.5 (3)	C11D—O1D—C1D—C6D	178.9 (3)
O1A—C1A—C2A—C3A	178.4 (3)	O1D—C1D—C2D—C3D	179.7 (3)
C6A—C1A—C2A—C3A	−2.2 (5)	C6D—C1D—C2D—C3D	0.0 (5)
C1A—C2A—C3A—C4A	0.7 (5)	C1D—C2D—C3D—C4D	−0.3 (5)
C2A—C3A—C4A—C5A	0.1 (5)	C2D—C3D—C4D—C5D	0.1 (5)
C2A—C3A—C4A—C7A	−178.9 (3)	C2D—C3D—C4D—C7D	−179.0 (3)
C3A—C4A—C5A—C6A	0.7 (5)	C3D—C4D—C5D—C6D	0.4 (5)
C7A—C4A—C5A—C6A	179.7 (3)	C7D—C4D—C5D—C6D	179.6 (3)
C4A—C5A—C6A—C1A	−2.2 (5)	C4D—C5D—C6D—C1D	−0.7 (5)
O1A—C1A—C6A—C5A	−177.6 (3)	O1D—C1D—C6D—C5D	−179.3 (3)
C2A—C1A—C6A—C5A	3.0 (5)	C2D—C1D—C6D—C5D	0.5 (5)
C5A—C4A—C7A—O3A	−5.3 (5)	C3D—C4D—C7D—O3D	173.8 (3)
C3A—C4A—C7A—O3A	173.7 (3)	C5D—C4D—C7D—O3D	−5.3 (5)
C5A—C4A—C7A—O2A	175.0 (3)	C3D—C4D—C7D—O2D	−6.9 (4)
C3A—C4A—C7A—O2A	−6.0 (5)	C5D—C4D—C7D—O2D	173.9 (3)
C1A—O1A—C11A—C12A	−178.9 (3)	C1D—O1D—C11D—C12D	−175.6 (3)
O1A—C11A—C12A—C13A	−178.8 (3)	O1D—C11D—C12D—C13D	176.9 (3)
C11A—C12A—C13A—C14A	178.4 (3)	C11D—C12D—C13D—C14D	178.1 (3)
C12A—C13A—C14A—C15A	178.5 (3)	C12D—C13D—C14D—C15D	175.6 (3)
C13A—C14A—C15A—C16A	179.1 (4)	C13D—C14D—C15D—C16D	−178.2 (3)
C11B—O1B—C1B—C2B	−3.0 (5)	C11E—O1E—C1E—C2E	−3.0 (5)
C11B—O1B—C1B—C6B	177.6 (3)	C11E—O1E—C1E—C6E	177.0 (3)
O1B—C1B—C2B—C3B	−177.8 (3)	O1E—C1E—C2E—C3E	−179.4 (3)
C6B—C1B—C2B—C3B	1.5 (5)	C6E—C1E—C2E—C3E	0.6 (5)
C1B—C2B—C3B—C4B	−0.6 (5)	C1E—C2E—C3E—C4E	−0.1 (5)
C2B—C3B—C4B—C5B	−0.6 (5)	C2E—C3E—C4E—C5E	−0.3 (5)
C2B—C3B—C4B—C7B	179.6 (3)	C2E—C3E—C4E—C7E	−179.8 (3)
C3B—C4B—C5B—C6B	0.9 (5)	C3E—C4E—C5E—C6E	0.2 (5)
C7B—C4B—C5B—C6B	−179.3 (3)	C7E—C4E—C5E—C6E	179.7 (3)
C4B—C5B—C6B—C1B	−0.1 (5)	C4E—C5E—C6E—C1E	0.3 (5)
O1B—C1B—C6B—C5B	178.2 (3)	O1E—C1E—C6E—C5E	179.3 (3)
C2B—C1B—C6B—C5B	−1.1 (5)	C2E—C1E—C6E—C5E	−0.7 (5)
C3B—C4B—C7B—O3B	−176.2 (3)	C3E—C4E—C7E—O3E	5.2 (5)
C5B—C4B—C7B—O3B	4.0 (5)	C5E—C4E—C7E—O3E	−174.2 (3)
C3B—C4B—C7B—O2B	4.1 (5)	C3E—C4E—C7E—O2E	−174.7 (3)
C5B—C4B—C7B—O2B	−175.7 (3)	C5E—C4E—C7E—O2E	5.8 (4)
C1B—O1B—C11B—C12B	179.5 (3)	C1E—O1E—C11E—C12E	−176.3 (3)
O1B—C11B—C12B—C13B	−175.5 (3)	O1E—C11E—C12E—C13E	−177.0 (3)
C11B—C12B—C13B—C14B	−179.4 (3)	C11E—C12E—C13E—C14E	−179.2 (3)
C12B—C13B—C14B—C15B	−179.1 (3)	C12E—C13E—C14E—C15E	177.6 (3)
C13B—C14B—C15B—C16B	−178.4 (3)	C13E—C14E—C15E—C16E	−177.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3^i	0.84	1.81	2.638 (4)	171
O2A—H2A···O3A^ii	0.84	1.81	2.644 (4)	173
O2B—H2B···O3C	0.84	1.83	2.663 (4)	174
O2C—H2C···O3B	0.84	1.84	2.679 (4)	175
O2D—H2D···O3E	0.84	1.81	2.647 (3)	172
O2E—H2E···O3D	0.84	1.84	2.675 (3)	174

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