Redetermination of 5,11,17,23-tetra-tert-butyl-25,27-di­(ethoxy­carbonyl­methoxy)-26,28-di­hydroxy­calix­[4]­arene chloro­form disolvate at low temperature

The title compound, C₅₂H₆₈O₈·2CHCl₃, previously reported by Ferguson et al. [Supramol. Chem. (1996), 7, 223-228], has been rerefined against new intensity data. The geometric parameters are comparable, as far as they are available. However, the results of the present structure determination are of significantly higher precision.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.094
• wR factor = 0.297
• Data-to-parameter ratio = 15.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



DIFMX_01  Alert C The maximum difference density is > 0.1*ZMAX*0.75
          _refine_diff_density_max given =      1.335
          Test value =      1.275

DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

RFACR_01  Alert C The value of the weighted R factor is > 0.25
          Weighted R factor given   0.297

PLAT_213  Alert C Atom C9C     has ADP max/min Ratio ...........       3.10 prolate

PLAT_213  Alert C Atom C11C    has ADP max/min Ratio ...........       4.00 prolate

PLAT_302  Alert C Anion/Solvent Disorder .......................      27.00 Perc.

PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      51.00 A   3


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 7 Alert Level C = Please check

---

S1. Comment

1,3-Diethers of calix[4]arenes with a syn orientation of the ether groups are easily available precursors for various derivatives (Collins et al., 1989). The title compound, (I), has been first described by Arnaud-Neu et al. (1989) and its structure has been reported some years ago (Ferguson et al., 1996) [(II) hereafter]; however, their crystal diffracted very weakly and the collected data were of quite low resolution [only 16% of the measured data could be labelled observed in the 2 to 20° θ range (I > 2σ(I)]. Thus, the aromatic rings had to be treated as rigid groups and restraints had been necessary for C—C and C—O bonds. In addition, the solvent could not be identified, but had to be treated with the SQUEEZE option in PLATON (Spek, 1990). Furthermore, no coordinates of (II) are available in the Cambridge Structural Database (Version 5.24 of November 2002; Allen, 2002). We present here the structure of (I) determined at low temperature from data with significantly higher precision. Since the coordinates of the published structure are not available, we had to restrict the comparision of both structure determinations to the values printed explicitely in the paper. We have labelled the atoms in the same way and Fig. 1 shows nearly the same view as for (II). The O···O distances, the interplanar angles between the aromatic rings and the shortest distance of the enclathrated ester residue to the guest molecule are comparable (Table 2). The molecule adopts the cone conformation which is stabilized by two intramolecular hydrogen bonds. One of the ester residues is located in the molecular cavity of a symmetry-related molecule. The shortest C···C distance from the terminal methyl group is C16A···C1Bⁱ 3.685 (6) Å [symmetry code: (i) 1/2 − x, 1/2 + y, z]. The reference plane of the calixarene, defined as the mean plane of the bridging C atoms (here C7A, C7B, C7C and C7D), is almost planar (r.m.s. deviation = 0.136 Å); the rings C1A–C6A, C1B–C6B, C1C–C6C, and C1D–C6D subtend angles of 64.91 (7), 57.81 (11), 67.10 (10) and 53.42 (12)°, respectively, to this plane.

S2. Experimental

The title diester was prepared in analogy to the literature by refluxing tert-butylcalix[4]arene with ethyl bromoacetate in dry acetonitrile in the presence of potassium carbonate. Single crystals formed during recrystallization from chloroform/methanol.

S3. Refinement

One of the two chloroform molecules is disordered over two sites. The site-occupation factors of the H atom and the three Cl atoms refined to 0.597 (7)/0.403 (7). All C—Cl distances were restrained to 1.78 (1) Å. H atoms bonded to C atoms were refined with fixed individual displacement parameters [U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl)] using a riding model with tertiary C—H = 1.00 Å, secondary C—H = 0.99 Å, methyl C—H = 0.98 Å and aromatic C—H = 0.95 Å. The hydroxyl H atoms were found in a difference map and were refined with fixed individual displacement parameters [U_iso(H) = 1.2U_eq(O)] using a riding model with O—H = 0.84 Å. In addition, the O—C torsion angle was allowed to refine. PLEASE PROVIDE LOCATION OF HIGHEST ELECTRON-DENSITY PEAK.

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).

Figures

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 30% probability level. H atoms bonded to C atoms and the solvent molecules have been omitted for clarity. Hydrogen bonds are shown as dotted lines.

(5,11,17,23-Tetra-tert-butyl-26,28-dihydroxy-25,27-bis(ethoxycarbonylmethoxy)-pen tacyclo(19.3.1.1^3,7.1^9,13.1^15,19)octacosa-1(25),3,5,7(28),9,11,13 (27),15, 17,19 (26),21,23-dodecaene) clathrate chloroform solvate

Crystal data

C52H68O8·2CHCl3	F(000) = 4480
Mr = 1059.80	Dx = 1.211 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8192 reflections
a = 17.7766 (2) Å	θ = 2.5–24.8°
b = 20.4108 (1) Å	µ = 0.34 mm^−1
c = 32.0452 (2) Å	T = 173 K
V = 11627.11 (16) Å^3	Block, colourless
Z = 8	0.43 × 0.32 × 0.28 mm

Data collection

Siemens SMART CCD three-circle diffractometer	10229 independent reflections
Radiation source: fine-focus sealed tube	6797 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→13
Tmin = 0.866, Tmax = 0.910	k = −24→24
52500 measured reflections	l = −37→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.095	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.297	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1605P)^2 + 26.7478P] where P = (Fo^2 + 2Fc^2)/3
10229 reflections	(Δ/σ)max = 0.001
643 parameters	Δρmax = 1.34 e Å^−3
27 restraints	Δρmin = −0.91 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.2358 (2)	0.70927 (18)	0.63617 (14)	0.0288 (9)
C2A	0.1984 (2)	0.69025 (19)	0.59968 (14)	0.0307 (9)
C3A	0.1338 (2)	0.6509 (2)	0.60422 (14)	0.0353 (10)
H3A	0.1077	0.6373	0.5798	0.042*
C4A	0.1066 (2)	0.6312 (2)	0.64289 (15)	0.0366 (10)
C5A	0.1480 (2)	0.6497 (2)	0.67828 (14)	0.0335 (10)
H5A	0.1308	0.6361	0.7050	0.040*
C6A	0.2138 (2)	0.68739 (18)	0.67585 (14)	0.0305 (9)
C7A	0.2275 (2)	0.7084 (2)	0.55623 (14)	0.0357 (10)
H7A1	0.2565	0.7497	0.5581	0.043*
H7A2	0.1842	0.7160	0.5375	0.043*
C8A	0.0344 (3)	0.5903 (3)	0.64869 (19)	0.0542 (14)
C9A	0.0535 (4)	0.5260 (3)	0.6716 (2)	0.0708 (18)
H9A1	0.0768	0.5362	0.6986	0.106*
H9A2	0.0884	0.5002	0.6547	0.106*
H9A3	0.0072	0.5009	0.6762	0.106*
C10A	−0.0016 (5)	0.5722 (6)	0.6072 (3)	0.129 (4)
H10A	−0.0144	0.6123	0.5919	0.193*
H10B	−0.0474	0.5467	0.6123	0.193*
H10C	0.0337	0.5461	0.5907	0.193*
C11A	−0.0217 (3)	0.6294 (4)	0.6764 (3)	0.080 (2)
H11A	0.0024	0.6405	0.7029	0.121*
H11B	−0.0665	0.6026	0.6817	0.121*
H11C	−0.0365	0.6697	0.6619	0.121*
O1A	0.30020 (16)	0.74934 (13)	0.63200 (10)	0.0337 (7)
C12A	0.2942 (3)	0.81436 (19)	0.64922 (15)	0.0376 (11)
H12A	0.3388	0.8236	0.6667	0.045*
H12B	0.2491	0.8169	0.6672	0.045*
C13A	0.2885 (3)	0.8660 (2)	0.61455 (16)	0.0368 (11)
O13A	0.3035 (2)	0.85760 (16)	0.57847 (12)	0.0617 (11)
O14A	0.2643 (2)	0.92169 (14)	0.63136 (10)	0.0427 (8)
C15A	0.2525 (3)	0.9781 (2)	0.60329 (16)	0.0459 (12)
H15A	0.2212	0.9651	0.5791	0.055*
H15B	0.3014	0.9946	0.5928	0.055*
C16A	0.2132 (3)	1.0301 (2)	0.62850 (16)	0.0406 (11)
H16A	0.2042	1.0686	0.6109	0.061*
H16B	0.2448	1.0425	0.6523	0.061*
H16C	0.1651	1.0131	0.6387	0.061*
C1B	0.3800 (2)	0.62714 (19)	0.71052 (12)	0.0276 (9)
C2B	0.3062 (2)	0.63527 (19)	0.72573 (13)	0.0281 (9)
C3B	0.2728 (2)	0.5842 (2)	0.74805 (13)	0.0299 (9)
H3B	0.2233	0.5900	0.7585	0.036*
C4B	0.3096 (2)	0.5247 (2)	0.75553 (13)	0.0291 (9)
C5B	0.3835 (2)	0.5190 (2)	0.74024 (13)	0.0297 (9)
H5B	0.4100	0.4793	0.7450	0.036*
C6B	0.4195 (2)	0.5689 (2)	0.71847 (12)	0.0272 (9)
C7B	0.2604 (2)	0.69727 (19)	0.71551 (13)	0.0319 (10)
H7B1	0.2266	0.7076	0.7391	0.038*
H7B2	0.2951	0.7348	0.7116	0.038*
C8B	0.2726 (2)	0.4665 (2)	0.77847 (14)	0.0359 (10)
C9B	0.3207 (3)	0.4470 (3)	0.81675 (18)	0.0562 (14)
H9B1	0.3721	0.4370	0.8077	0.084*
H9B2	0.2987	0.4084	0.8302	0.084*
H9B3	0.3218	0.4835	0.8367	0.084*
C10B	0.2677 (3)	0.4080 (3)	0.74788 (19)	0.0585 (15)
H10D	0.3182	0.3969	0.7379	0.088*
H10E	0.2359	0.4200	0.7241	0.088*
H10F	0.2459	0.3701	0.7622	0.088*
C11B	0.1922 (3)	0.4821 (3)	0.79317 (18)	0.0505 (13)
H11D	0.1711	0.4439	0.8075	0.076*
H11E	0.1609	0.4931	0.7690	0.076*
H11F	0.1935	0.5194	0.8124	0.076*
O1B	0.41094 (16)	0.67880 (13)	0.68845 (10)	0.0357 (7)
H1B	0.4450	0.6647	0.6726	0.043*
C1C	0.5031 (2)	0.57237 (19)	0.62265 (13)	0.0265 (9)
C2C	0.4998 (2)	0.5317 (2)	0.65787 (13)	0.0268 (9)
C3C	0.4894 (2)	0.4645 (2)	0.65145 (14)	0.0318 (10)
H3C	0.4886	0.4361	0.6749	0.038*
C4C	0.4800 (2)	0.4376 (2)	0.61150 (14)	0.0305 (9)
C5C	0.4785 (2)	0.4810 (2)	0.57781 (14)	0.0296 (9)
H5C	0.4698	0.4640	0.5507	0.035*
C6C	0.4892 (2)	0.54859 (19)	0.58237 (13)	0.0257 (9)
C7C	0.5000 (2)	0.5585 (2)	0.70255 (13)	0.0314 (9)
H7C1	0.5276	0.6006	0.7033	0.038*
H7C2	0.5264	0.5272	0.7211	0.038*
C8C	0.4726 (3)	0.3624 (2)	0.60559 (16)	0.0415 (11)
C9C	0.4293 (7)	0.3447 (3)	0.5662 (2)	0.120 (4)
H9C1	0.3789	0.3640	0.5675	0.180*
H9C2	0.4251	0.2969	0.5641	0.180*
H9C3	0.4561	0.3617	0.5418	0.180*
C10C	0.4276 (5)	0.3319 (3)	0.6411 (2)	0.094 (3)
H10G	0.3768	0.3505	0.6414	0.141*
H10H	0.4526	0.3412	0.6677	0.141*
H10I	0.4245	0.2844	0.6370	0.141*
C11C	0.5500 (4)	0.3340 (3)	0.6051 (5)	0.159 (6)
H11G	0.5763	0.3462	0.6309	0.239*
H11H	0.5777	0.3510	0.5810	0.239*
H11I	0.5467	0.2861	0.6032	0.239*
O1C	0.51613 (16)	0.63967 (13)	0.62944 (9)	0.0322 (7)
C12C	0.5854 (3)	0.6645 (2)	0.61329 (16)	0.0403 (11)
H12C	0.5770	0.7093	0.6025	0.048*
H12D	0.6014	0.6367	0.5896	0.048*
C13C	0.6481 (3)	0.6663 (2)	0.64553 (19)	0.0468 (12)
O13C	0.6426 (2)	0.6557 (2)	0.68184 (13)	0.0647 (11)
O14C	0.7129 (2)	0.6827 (2)	0.62518 (14)	0.0738 (13)
C15C	0.7813 (4)	0.6906 (4)	0.6503 (3)	0.087 (2)
H15C	0.7821	0.6573	0.6728	0.104*
H15D	0.8261	0.6837	0.6325	0.104*
C16C	0.7841 (6)	0.7560 (5)	0.6686 (3)	0.117 (3)
H16D	0.8301	0.7606	0.6852	0.175*
H16E	0.7401	0.7625	0.6866	0.175*
H16F	0.7839	0.7889	0.6463	0.175*
C1D	0.3546 (2)	0.65070 (19)	0.54712 (13)	0.0281 (9)
C2D	0.3985 (2)	0.59982 (19)	0.53050 (12)	0.0280 (9)
C3D	0.3658 (2)	0.5555 (2)	0.50306 (13)	0.0342 (10)
H3D	0.3965	0.5222	0.4913	0.041*
C4D	0.2900 (3)	0.5577 (2)	0.49192 (15)	0.0403 (11)
C5D	0.2469 (3)	0.6083 (2)	0.51016 (14)	0.0410 (11)
H5D	0.1948	0.6110	0.5037	0.049*
C6D	0.2777 (2)	0.6550 (2)	0.53747 (13)	0.0314 (9)
C7D	0.4813 (2)	0.5931 (2)	0.54386 (13)	0.0294 (9)
H7D1	0.5019	0.6370	0.5504	0.035*
H7D2	0.5109	0.5746	0.5205	0.035*
C8D	0.2577 (3)	0.5077 (3)	0.46033 (17)	0.0537 (14)
C9D	0.1742 (4)	0.5160 (5)	0.4543 (3)	0.111 (3)
H9D1	0.1486	0.5117	0.4812	0.167*
H9D2	0.1557	0.4823	0.4351	0.167*
H9D3	0.1640	0.5595	0.4426	0.167*
C10D	0.2747 (4)	0.4362 (3)	0.4761 (2)	0.082 (2)
H10J	0.3290	0.4309	0.4801	0.123*
H10K	0.2568	0.4044	0.4554	0.123*
H10L	0.2488	0.4287	0.5027	0.123*
C11D	0.2991 (4)	0.5143 (4)	0.4185 (2)	0.0742 (19)
H11J	0.3533	0.5088	0.4230	0.111*
H11K	0.2894	0.5577	0.4066	0.111*
H11L	0.2811	0.4805	0.3992	0.111*
O1D	0.39059 (16)	0.69522 (14)	0.57270 (10)	0.0372 (7)
H1D	0.3588	0.7137	0.5882	0.045*
C1L	0.4937 (3)	0.7990 (3)	0.71893 (18)	0.080 (2)
H1L	0.4583	0.7609	0.7179	0.095*
Cl11	0.44813 (13)	0.86633 (11)	0.74096 (8)	0.1135 (9)
Cl12	0.5208 (2)	0.82055 (14)	0.66748 (10)	0.1465 (12)
Cl13	0.57275 (15)	0.77778 (15)	0.74781 (11)	0.1488 (13)
C2L	0.4586 (3)	0.8301 (3)	0.5313 (2)	0.105 (3)
H2L1	0.4322	0.8152	0.5572	0.126*	0.597 (7)
H2L2	0.4085	0.8079	0.5297	0.126*	0.403 (7)
Cl21	0.5452 (3)	0.7911 (4)	0.5259 (3)	0.147 (4)	0.597 (7)
Cl22	0.4720 (5)	0.9138 (3)	0.5319 (5)	0.217 (6)	0.597 (7)
Cl23	0.4036 (4)	0.8081 (3)	0.48384 (15)	0.160 (3)	0.597 (7)
Cl24	0.4932 (6)	0.8514 (7)	0.5850 (3)	0.211 (6)	0.403 (7)
Cl25	0.5355 (9)	0.7854 (7)	0.5136 (6)	0.235 (10)	0.403 (7)
Cl26	0.4625 (8)	0.9116 (4)	0.5126 (3)	0.137 (5)	0.403 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.023 (2)	0.0238 (18)	0.039 (3)	0.0072 (15)	0.0034 (18)	−0.0009 (17)
C2A	0.030 (2)	0.0269 (19)	0.036 (3)	0.0086 (16)	0.0003 (18)	−0.0009 (18)
C3A	0.032 (2)	0.039 (2)	0.035 (3)	0.0065 (18)	−0.0048 (19)	−0.004 (2)
C4A	0.028 (2)	0.040 (2)	0.042 (3)	0.0004 (18)	−0.003 (2)	0.003 (2)
C5A	0.026 (2)	0.037 (2)	0.038 (3)	0.0036 (17)	0.0039 (19)	0.0057 (19)
C6A	0.030 (2)	0.0248 (19)	0.037 (3)	0.0087 (16)	0.0013 (19)	−0.0017 (17)
C7A	0.033 (2)	0.042 (2)	0.033 (3)	0.0111 (19)	−0.0016 (19)	0.0049 (19)
C8A	0.037 (3)	0.063 (3)	0.062 (4)	−0.017 (2)	−0.007 (3)	0.011 (3)
C9A	0.059 (4)	0.064 (4)	0.090 (5)	−0.024 (3)	−0.002 (3)	0.015 (3)
C10A	0.094 (6)	0.206 (11)	0.086 (6)	−0.100 (7)	−0.037 (5)	0.041 (6)
C11A	0.033 (3)	0.091 (5)	0.117 (6)	−0.007 (3)	0.007 (3)	0.025 (4)
O1A	0.0302 (15)	0.0255 (13)	0.0453 (19)	0.0017 (12)	0.0047 (13)	0.0000 (13)
C12A	0.042 (3)	0.026 (2)	0.045 (3)	0.0025 (18)	−0.006 (2)	−0.0035 (19)
C13A	0.039 (2)	0.028 (2)	0.044 (3)	−0.0041 (18)	0.007 (2)	−0.0022 (19)
O13A	0.094 (3)	0.0375 (18)	0.054 (2)	0.0093 (18)	0.033 (2)	0.0049 (17)
O14A	0.065 (2)	0.0261 (15)	0.0370 (18)	0.0043 (14)	0.0056 (16)	0.0029 (13)
C15A	0.064 (3)	0.032 (2)	0.041 (3)	0.001 (2)	0.006 (2)	0.007 (2)
C16A	0.044 (3)	0.027 (2)	0.051 (3)	−0.0006 (19)	−0.003 (2)	0.003 (2)
C1B	0.029 (2)	0.031 (2)	0.023 (2)	−0.0050 (16)	0.0010 (17)	−0.0042 (17)
C2B	0.027 (2)	0.032 (2)	0.026 (2)	0.0004 (16)	−0.0016 (17)	−0.0055 (17)
C3B	0.024 (2)	0.036 (2)	0.029 (2)	0.0045 (17)	0.0028 (17)	−0.0031 (18)
C4B	0.030 (2)	0.034 (2)	0.023 (2)	0.0000 (17)	0.0003 (17)	−0.0023 (17)
C5B	0.031 (2)	0.031 (2)	0.027 (2)	0.0063 (17)	−0.0007 (18)	−0.0024 (17)
C6B	0.0220 (19)	0.037 (2)	0.023 (2)	0.0020 (16)	−0.0023 (16)	−0.0090 (17)
C7B	0.035 (2)	0.028 (2)	0.032 (2)	0.0034 (17)	0.0032 (19)	−0.0049 (17)
C8B	0.034 (2)	0.036 (2)	0.038 (3)	0.0028 (18)	0.003 (2)	0.0036 (19)
C9B	0.048 (3)	0.068 (3)	0.052 (3)	−0.001 (3)	0.000 (3)	0.026 (3)
C10B	0.067 (4)	0.043 (3)	0.066 (4)	−0.013 (3)	0.014 (3)	−0.004 (3)
C11B	0.038 (3)	0.052 (3)	0.061 (4)	0.001 (2)	0.017 (2)	0.014 (3)
O1B	0.0321 (16)	0.0293 (14)	0.046 (2)	−0.0043 (12)	0.0079 (14)	−0.0035 (13)
C1C	0.0177 (18)	0.030 (2)	0.032 (2)	−0.0003 (15)	0.0031 (16)	−0.0027 (17)
C2C	0.0161 (18)	0.037 (2)	0.027 (2)	0.0035 (15)	−0.0009 (16)	−0.0020 (17)
C3C	0.028 (2)	0.033 (2)	0.035 (3)	0.0051 (17)	0.0024 (18)	0.0031 (18)
C4C	0.025 (2)	0.031 (2)	0.036 (2)	0.0002 (16)	0.0020 (18)	−0.0020 (18)
C5C	0.025 (2)	0.034 (2)	0.030 (2)	−0.0014 (16)	0.0030 (17)	−0.0058 (18)
C6C	0.0169 (18)	0.032 (2)	0.028 (2)	0.0011 (15)	0.0036 (16)	0.0018 (17)
C7C	0.022 (2)	0.041 (2)	0.031 (2)	0.0005 (17)	−0.0040 (17)	−0.0010 (19)
C8C	0.045 (3)	0.030 (2)	0.050 (3)	−0.0009 (19)	0.005 (2)	0.000 (2)
C9C	0.249 (12)	0.041 (3)	0.072 (5)	−0.045 (5)	−0.039 (6)	−0.005 (3)
C10C	0.142 (7)	0.055 (4)	0.084 (5)	−0.047 (4)	0.028 (5)	−0.003 (3)
C11C	0.060 (4)	0.036 (3)	0.382 (18)	0.015 (3)	0.017 (7)	−0.035 (6)
O1C	0.0281 (15)	0.0307 (15)	0.0377 (17)	−0.0036 (12)	0.0013 (13)	−0.0078 (12)
C12C	0.034 (2)	0.041 (2)	0.045 (3)	−0.012 (2)	0.001 (2)	−0.006 (2)
C13C	0.040 (3)	0.045 (3)	0.056 (4)	−0.014 (2)	−0.005 (2)	0.002 (2)
O13C	0.050 (2)	0.086 (3)	0.058 (3)	−0.029 (2)	−0.0183 (19)	0.021 (2)
O14C	0.038 (2)	0.108 (3)	0.075 (3)	−0.025 (2)	−0.003 (2)	−0.007 (2)
C15C	0.047 (4)	0.124 (7)	0.090 (5)	−0.014 (4)	−0.012 (3)	0.013 (5)
C16C	0.120 (7)	0.132 (8)	0.098 (6)	−0.061 (6)	−0.002 (5)	−0.026 (6)
C1D	0.027 (2)	0.032 (2)	0.025 (2)	−0.0014 (17)	0.0021 (17)	0.0041 (17)
C2D	0.028 (2)	0.031 (2)	0.025 (2)	−0.0029 (17)	0.0033 (17)	0.0020 (17)
C3D	0.034 (2)	0.043 (2)	0.026 (2)	0.0016 (19)	0.0030 (18)	−0.0063 (19)
C4D	0.036 (3)	0.053 (3)	0.031 (3)	−0.002 (2)	0.000 (2)	−0.010 (2)
C5D	0.028 (2)	0.061 (3)	0.034 (3)	0.000 (2)	−0.005 (2)	0.000 (2)
C6D	0.030 (2)	0.039 (2)	0.026 (2)	0.0065 (18)	0.0004 (18)	0.0042 (18)
C7D	0.025 (2)	0.035 (2)	0.029 (2)	−0.0004 (17)	0.0054 (17)	−0.0009 (17)
C8D	0.042 (3)	0.073 (4)	0.046 (3)	−0.007 (3)	−0.004 (2)	−0.017 (3)
C9D	0.045 (4)	0.161 (8)	0.127 (7)	0.003 (4)	−0.019 (4)	−0.092 (6)
C10D	0.094 (5)	0.078 (5)	0.073 (5)	−0.020 (4)	−0.011 (4)	−0.028 (4)
C11D	0.065 (4)	0.102 (5)	0.056 (4)	0.002 (4)	−0.010 (3)	−0.032 (4)
O1D	0.0305 (16)	0.0337 (16)	0.048 (2)	−0.0004 (12)	0.0052 (14)	−0.0102 (14)
C1L	0.072 (4)	0.054 (3)	0.112 (6)	−0.015 (3)	−0.002 (4)	−0.031 (4)
Cl11	0.1025 (16)	0.1004 (15)	0.138 (2)	0.0437 (12)	−0.0365 (14)	−0.0558 (14)
Cl12	0.176 (3)	0.1086 (19)	0.155 (3)	−0.0441 (18)	0.057 (2)	−0.0333 (17)
Cl13	0.0991 (17)	0.133 (2)	0.214 (3)	0.0563 (16)	−0.0430 (19)	−0.053 (2)
C2L	0.101 (6)	0.087 (5)	0.127 (8)	0.014 (5)	0.048 (6)	0.020 (5)
Cl21	0.090 (3)	0.111 (5)	0.238 (8)	0.043 (3)	0.085 (4)	0.092 (5)
Cl22	0.098 (4)	0.076 (4)	0.476 (19)	−0.014 (3)	0.045 (8)	−0.048 (6)
Cl23	0.217 (7)	0.169 (5)	0.094 (3)	−0.001 (4)	0.034 (4)	0.012 (3)
Cl24	0.152 (9)	0.259 (14)	0.223 (12)	0.000 (8)	0.002 (8)	−0.048 (10)
Cl25	0.36 (2)	0.095 (7)	0.254 (14)	0.043 (9)	0.244 (15)	0.006 (7)
Cl26	0.188 (11)	0.093 (6)	0.130 (6)	0.046 (6)	0.043 (6)	0.058 (5)

Geometric parameters (Å, º)

C1A—C2A	1.400 (6)	C3C—C4C	1.403 (6)
C1A—C6A	1.403 (6)	C3C—H3C	0.9500
C1A—O1A	1.413 (5)	C4C—C5C	1.397 (6)
C2A—C3A	1.409 (6)	C4C—C8C	1.553 (6)
C2A—C7A	1.531 (6)	C5C—C6C	1.400 (6)
C3A—C4A	1.390 (7)	C5C—H5C	0.9500
C3A—H3A	0.9500	C6C—C7D	1.539 (6)
C4A—C5A	1.404 (6)	C7C—H7C1	0.9900
C4A—C8A	1.542 (6)	C7C—H7C2	0.9900
C5A—C6A	1.403 (6)	C8C—C11C	1.493 (8)
C5A—H5A	0.9500	C8C—C9C	1.521 (9)
C6A—C7B	1.531 (6)	C8C—C10C	1.524 (8)
C7A—C6D	1.532 (6)	C9C—H9C1	0.9800
C7A—H7A1	0.9900	C9C—H9C2	0.9800
C7A—H7A2	0.9900	C9C—H9C3	0.9800
C8A—C10A	1.520 (10)	C10C—H10G	0.9800
C8A—C9A	1.541 (8)	C10C—H10H	0.9800
C8A—C11A	1.556 (9)	C10C—H10I	0.9800
C9A—H9A1	0.9800	C11C—H11G	0.9800
C9A—H9A2	0.9800	C11C—H11H	0.9800
C9A—H9A3	0.9800	C11C—H11I	0.9800
C10A—H10A	0.9800	O1C—C12C	1.428 (5)
C10A—H10B	0.9800	C12C—C13C	1.520 (7)
C10A—H10C	0.9800	C12C—H12C	0.9900
C11A—H11A	0.9800	C12C—H12D	0.9900
C11A—H11B	0.9800	C13C—O13C	1.188 (6)
C11A—H11C	0.9800	C13C—O14C	1.366 (6)
O1A—C12A	1.441 (5)	O14C—C15C	1.468 (8)
C12A—C13A	1.535 (6)	C15C—C16C	1.459 (11)
C12A—H12A	0.9900	C15C—H15C	0.9900
C12A—H12B	0.9900	C15C—H15D	0.9900
C13A—O13A	1.199 (6)	C16C—H16D	0.9800
C13A—O14A	1.329 (5)	C16C—H16E	0.9800
O14A—C15A	1.476 (5)	C16C—H16F	0.9800
C15A—C16A	1.506 (7)	C1D—O1D	1.381 (5)
C15A—H15A	0.9900	C1D—C2D	1.404 (6)
C15A—H15B	0.9900	C1D—C6D	1.404 (6)
C16A—H16A	0.9800	C2D—C3D	1.389 (6)
C16A—H16B	0.9800	C2D—C7D	1.540 (6)
C16A—H16C	0.9800	C3D—C4D	1.395 (7)
C1B—O1B	1.384 (5)	C3D—H3D	0.9500
C1B—C6B	1.404 (6)	C4D—C5D	1.413 (7)
C1B—C2B	1.408 (6)	C4D—C8D	1.548 (7)
C2B—C3B	1.397 (6)	C5D—C6D	1.404 (6)
C2B—C7B	1.540 (6)	C5D—H5D	0.9500
C3B—C4B	1.400 (6)	C7D—H7D1	0.9900
C3B—H3B	0.9500	C7D—H7D2	0.9900
C4B—C5B	1.407 (6)	C8D—C9D	1.506 (8)
C4B—C8B	1.544 (6)	C8D—C11D	1.535 (9)
C5B—C6B	1.391 (6)	C8D—C10D	1.574 (9)
C5B—H5B	0.9500	C9D—H9D1	0.9800
C6B—C7C	1.533 (5)	C9D—H9D2	0.9800
C7B—H7B1	0.9900	C9D—H9D3	0.9800
C7B—H7B2	0.9900	C10D—H10J	0.9800
C8B—C10B	1.547 (7)	C10D—H10K	0.9800
C8B—C11B	1.537 (6)	C10D—H10L	0.9800
C8B—C9B	1.547 (7)	C11D—H11J	0.9800
C9B—H9B1	0.9800	C11D—H11K	0.9800
C9B—H9B2	0.9800	C11D—H11L	0.9800
C9B—H9B3	0.9800	O1D—H1D	0.8400
C10B—H10D	0.9800	C1L—Cl13	1.737 (6)
C10B—H10E	0.9800	C1L—Cl11	1.745 (5)
C10B—H10F	0.9800	C1L—Cl12	1.773 (6)
C11B—H11D	0.9800	C1L—H1L	1.0000
C11B—H11E	0.9800	C2L—Cl22	1.726 (7)
C11B—H11F	0.9800	C2L—Cl25	1.740 (8)
O1B—H1B	0.8400	C2L—Cl21	1.742 (6)
C1C—C6C	1.401 (6)	C2L—Cl26	1.770 (7)
C1C—C2C	1.402 (6)	C2L—Cl23	1.864 (7)
C1C—O1C	1.410 (5)	C2L—Cl24	1.879 (8)
C2C—C3C	1.401 (6)	C2L—H2L1	1.0000
C2C—C7C	1.532 (6)	C2L—H2L2	1.0000
C2A—C1A—C6A	122.5 (4)	C5C—C4C—C3C	117.4 (4)
C2A—C1A—O1A	117.8 (4)	C5C—C4C—C8C	122.1 (4)
C6A—C1A—O1A	119.7 (4)	C3C—C4C—C8C	120.5 (4)
C1A—C2A—C3A	117.3 (4)	C4C—C5C—C6C	122.8 (4)
C1A—C2A—C7A	122.2 (4)	C4C—C5C—H5C	118.6
C3A—C2A—C7A	120.5 (4)	C6C—C5C—H5C	118.6
C4A—C3A—C2A	122.7 (4)	C1C—C6C—C5C	117.5 (4)
C4A—C3A—H3A	118.6	C1C—C6C—C7D	123.4 (4)
C2A—C3A—H3A	118.6	C5C—C6C—C7D	119.1 (4)
C3A—C4A—C5A	117.4 (4)	C2C—C7C—C6B	111.0 (3)
C3A—C4A—C8A	123.6 (4)	C2C—C7C—H7C1	109.4
C5A—C4A—C8A	119.0 (4)	C6B—C7C—H7C1	109.4
C6A—C5A—C4A	122.7 (4)	C2C—C7C—H7C2	109.4
C6A—C5A—H5A	118.7	C6B—C7C—H7C2	109.4
C4A—C5A—H5A	118.7	H7C1—C7C—H7C2	108.0
C1A—C6A—C5A	117.2 (4)	C11C—C8C—C9C	111.4 (7)
C1A—C6A—C7B	124.1 (4)	C11C—C8C—C10C	109.4 (7)
C5A—C6A—C7B	118.5 (4)	C9C—C8C—C10C	104.9 (6)
C2A—C7A—C6D	112.5 (3)	C11C—C8C—C4C	107.9 (4)
C2A—C7A—H7A1	109.1	C9C—C8C—C4C	112.3 (4)
C6D—C7A—H7A1	109.1	C10C—C8C—C4C	110.9 (4)
C2A—C7A—H7A2	109.1	C8C—C9C—H9C1	109.5
C6D—C7A—H7A2	109.1	C8C—C9C—H9C2	109.5
H7A1—C7A—H7A2	107.8	H9C1—C9C—H9C2	109.5
C10A—C8A—C9A	107.7 (6)	C8C—C9C—H9C3	109.5
C10A—C8A—C4A	112.1 (5)	H9C1—C9C—H9C3	109.5
C9A—C8A—C4A	109.6 (4)	H9C2—C9C—H9C3	109.5
C10A—C8A—C11A	110.6 (6)	C8C—C10C—H10G	109.5
C9A—C8A—C11A	107.8 (5)	C8C—C10C—H10H	109.5
C4A—C8A—C11A	109.0 (5)	H10G—C10C—H10H	109.5
C8A—C9A—H9A1	109.5	C8C—C10C—H10I	109.5
C8A—C9A—H9A2	109.5	H10G—C10C—H10I	109.5
H9A1—C9A—H9A2	109.5	H10H—C10C—H10I	109.5
C8A—C9A—H9A3	109.5	C8C—C11C—H11G	109.5
H9A1—C9A—H9A3	109.5	C8C—C11C—H11H	109.5
H9A2—C9A—H9A3	109.5	H11G—C11C—H11H	109.5
C8A—C10A—H10A	109.5	C8C—C11C—H11I	109.5
C8A—C10A—H10B	109.5	H11G—C11C—H11I	109.5
H10A—C10A—H10B	109.5	H11H—C11C—H11I	109.5
C8A—C10A—H10C	109.5	C1C—O1C—C12C	115.5 (3)
H10A—C10A—H10C	109.5	O1C—C12C—C13C	113.2 (4)
H10B—C10A—H10C	109.5	O1C—C12C—H12C	108.9
C8A—C11A—H11A	109.5	C13C—C12C—H12C	108.9
C8A—C11A—H11B	109.5	O1C—C12C—H12D	108.9
H11A—C11A—H11B	109.5	C13C—C12C—H12D	108.9
C8A—C11A—H11C	109.5	H12C—C12C—H12D	107.7
H11A—C11A—H11C	109.5	O13C—C13C—O14C	125.6 (5)
H11B—C11A—H11C	109.5	O13C—C13C—C12C	127.0 (5)
C1A—O1A—C12A	115.9 (3)	O14C—C13C—C12C	107.5 (5)
O1A—C12A—C13A	111.1 (4)	C13C—O14C—C15C	117.7 (5)
O1A—C12A—H12A	109.4	C16C—C15C—O14C	110.4 (7)
C13A—C12A—H12A	109.4	C16C—C15C—H15C	109.6
O1A—C12A—H12B	109.4	O14C—C15C—H15C	109.6
C13A—C12A—H12B	109.4	C16C—C15C—H15D	109.6
H12A—C12A—H12B	108.0	O14C—C15C—H15D	109.6
O13A—C13A—O14A	125.8 (4)	H15C—C15C—H15D	108.1
O13A—C13A—C12A	125.8 (4)	C15C—C16C—H16D	109.5
O14A—C13A—C12A	108.4 (4)	C15C—C16C—H16E	109.5
C13A—O14A—C15A	117.8 (4)	H16D—C16C—H16E	109.5
O14A—C15A—C16A	106.8 (4)	C15C—C16C—H16F	109.5
O14A—C15A—H15A	110.4	H16D—C16C—H16F	109.5
C16A—C15A—H15A	110.4	H16E—C16C—H16F	109.5
O14A—C15A—H15B	110.4	O1D—C1D—C2D	117.0 (4)
C16A—C15A—H15B	110.4	O1D—C1D—C6D	122.8 (4)
H15A—C15A—H15B	108.6	C2D—C1D—C6D	120.2 (4)
C15A—C16A—H16A	109.5	C3D—C2D—C1D	119.3 (4)
C15A—C16A—H16B	109.5	C3D—C2D—C7D	121.2 (4)
H16A—C16A—H16B	109.5	C1D—C2D—C7D	119.5 (4)
C15A—C16A—H16C	109.5	C2D—C3D—C4D	123.1 (4)
H16A—C16A—H16C	109.5	C2D—C3D—H3D	118.5
H16B—C16A—H16C	109.5	C4D—C3D—H3D	118.5
O1B—C1B—C6B	122.6 (4)	C3D—C4D—C5D	116.2 (4)
O1B—C1B—C2B	117.2 (3)	C3D—C4D—C8D	120.3 (4)
C6B—C1B—C2B	120.2 (4)	C5D—C4D—C8D	123.5 (4)
C3B—C2B—C1B	119.0 (4)	C6D—C5D—C4D	122.8 (4)
C3B—C2B—C7B	119.9 (4)	C6D—C5D—H5D	118.6
C1B—C2B—C7B	121.0 (4)	C4D—C5D—H5D	118.6
C2B—C3B—C4B	122.5 (4)	C1D—C6D—C5D	118.4 (4)
C2B—C3B—H3B	118.8	C1D—C6D—C7A	121.7 (4)
C4B—C3B—H3B	118.8	C5D—C6D—C7A	120.0 (4)
C3B—C4B—C5B	116.6 (4)	C2D—C7D—C6C	111.2 (3)
C3B—C4B—C8B	123.3 (4)	C2D—C7D—H7D1	109.4
C5B—C4B—C8B	120.0 (4)	C6C—C7D—H7D1	109.4
C6B—C5B—C4B	123.0 (4)	C2D—C7D—H7D2	109.4
C6B—C5B—H5B	118.5	C6C—C7D—H7D2	109.4
C4B—C5B—H5B	118.5	H7D1—C7D—H7D2	108.0
C5B—C6B—C1B	118.7 (4)	C9D—C8D—C11D	110.5 (6)
C5B—C6B—C7C	119.6 (4)	C9D—C8D—C4D	112.0 (5)
C1B—C6B—C7C	121.7 (4)	C11D—C8D—C4D	109.6 (5)
C6A—C7B—C2B	110.8 (3)	C9D—C8D—C10D	109.6 (6)
C6A—C7B—H7B1	109.5	C11D—C8D—C10D	105.7 (5)
C2B—C7B—H7B1	109.5	C4D—C8D—C10D	109.3 (5)
C6A—C7B—H7B2	109.5	C8D—C9D—H9D1	109.5
C2B—C7B—H7B2	109.5	C8D—C9D—H9D2	109.5
H7B1—C7B—H7B2	108.1	H9D1—C9D—H9D2	109.5
C10B—C8B—C11B	107.6 (4)	C8D—C9D—H9D3	109.5
C10B—C8B—C4B	108.4 (4)	H9D1—C9D—H9D3	109.5
C11B—C8B—C4B	112.5 (4)	H9D2—C9D—H9D3	109.5
C10B—C8B—C9B	109.6 (4)	C8D—C10D—H10J	109.5
C11B—C8B—C9B	108.9 (4)	C8D—C10D—H10K	109.5
C4B—C8B—C9B	109.8 (4)	H10J—C10D—H10K	109.5
C8B—C9B—H9B1	109.5	C8D—C10D—H10L	109.5
C8B—C9B—H9B2	109.5	H10J—C10D—H10L	109.5
H9B1—C9B—H9B2	109.5	H10K—C10D—H10L	109.5
C8B—C9B—H9B3	109.5	C8D—C11D—H11J	109.5
H9B1—C9B—H9B3	109.5	C8D—C11D—H11K	109.5
H9B2—C9B—H9B3	109.5	H11J—C11D—H11K	109.5
C8B—C10B—H10D	109.5	C8D—C11D—H11L	109.5
C8B—C10B—H10E	109.5	H11J—C11D—H11L	109.5
H10D—C10B—H10E	109.5	H11K—C11D—H11L	109.5
C8B—C10B—H10F	109.5	C1D—O1D—H1D	109.5
H10D—C10B—H10F	109.5	Cl13—C1L—Cl11	110.9 (3)
H10E—C10B—H10F	109.5	Cl13—C1L—Cl12	109.7 (4)
C8B—C11B—H11D	109.5	Cl11—C1L—Cl12	107.8 (3)
C8B—C11B—H11E	109.5	Cl13—C1L—H1L	109.5
H11D—C11B—H11E	109.5	Cl11—C1L—H1L	109.5
C8B—C11B—H11F	109.5	Cl12—C1L—H1L	109.5
H11D—C11B—H11F	109.5	Cl22—C2L—Cl21	109.3 (5)
H11E—C11B—H11F	109.5	Cl25—C2L—Cl26	110.6 (7)
C1B—O1B—H1B	109.5	Cl22—C2L—Cl23	108.7 (6)
C6C—C1C—C2C	122.0 (4)	Cl21—C2L—Cl23	105.8 (5)
C6C—C1C—O1C	120.6 (4)	Cl25—C2L—Cl24	99.4 (8)
C2C—C1C—O1C	117.3 (4)	Cl26—C2L—Cl24	94.6 (6)
C1C—C2C—C3C	117.9 (4)	Cl22—C2L—H2L1	111.0
C1C—C2C—C7C	122.8 (4)	Cl21—C2L—H2L1	111.0
C3C—C2C—C7C	119.1 (4)	Cl23—C2L—H2L1	111.0
C4C—C3C—C2C	122.2 (4)	Cl25—C2L—H2L2	116.4
C4C—C3C—H3C	118.9	Cl26—C2L—H2L2	116.4
C2C—C3C—H3C	118.9	Cl24—C2L—H2L2	116.4
C6A—C1A—C2A—C3A	3.9 (6)	C6C—C1C—C2C—C7C	−168.1 (3)
O1A—C1A—C2A—C3A	−179.3 (3)	O1C—C1C—C2C—C7C	7.8 (5)
C6A—C1A—C2A—C7A	−173.4 (4)	C1C—C2C—C3C—C4C	−2.0 (6)
O1A—C1A—C2A—C7A	3.3 (5)	C7C—C2C—C3C—C4C	172.6 (4)
C1A—C2A—C3A—C4A	0.3 (6)	C2C—C3C—C4C—C5C	−2.4 (6)
C7A—C2A—C3A—C4A	177.6 (4)	C2C—C3C—C4C—C8C	176.9 (4)
C2A—C3A—C4A—C5A	−2.6 (6)	C3C—C4C—C5C—C6C	2.9 (6)
C2A—C3A—C4A—C8A	177.7 (4)	C8C—C4C—C5C—C6C	−176.4 (4)
C3A—C4A—C5A—C6A	0.9 (6)	C2C—C1C—C6C—C5C	−5.7 (5)
C8A—C4A—C5A—C6A	−179.3 (4)	O1C—C1C—C6C—C5C	178.5 (3)
C2A—C1A—C6A—C5A	−5.5 (6)	C2C—C1C—C6C—C7D	171.1 (3)
O1A—C1A—C6A—C5A	177.9 (3)	O1C—C1C—C6C—C7D	−4.6 (5)
C2A—C1A—C6A—C7B	169.2 (4)	C4C—C5C—C6C—C1C	1.0 (6)
O1A—C1A—C6A—C7B	−7.5 (5)	C4C—C5C—C6C—C7D	−176.0 (4)
C4A—C5A—C6A—C1A	2.9 (6)	C1C—C2C—C7C—C6B	92.2 (4)
C4A—C5A—C6A—C7B	−172.0 (4)	C3C—C2C—C7C—C6B	−82.1 (5)
C1A—C2A—C7A—C6D	93.3 (5)	C5B—C6B—C7C—C2C	92.1 (5)
C3A—C2A—C7A—C6D	−83.9 (5)	C1B—C6B—C7C—C2C	−85.8 (5)
C3A—C4A—C8A—C10A	2.0 (8)	C5C—C4C—C8C—C11C	96.6 (7)
C5A—C4A—C8A—C10A	−177.7 (6)	C3C—C4C—C8C—C11C	−82.7 (7)
C3A—C4A—C8A—C9A	121.5 (5)	C5C—C4C—C8C—C9C	−26.6 (7)
C5A—C4A—C8A—C9A	−58.2 (6)	C3C—C4C—C8C—C9C	154.1 (6)
C3A—C4A—C8A—C11A	−120.7 (5)	C5C—C4C—C8C—C10C	−143.5 (5)
C5A—C4A—C8A—C11A	59.6 (6)	C3C—C4C—C8C—C10C	37.2 (7)
C2A—C1A—O1A—C12A	115.0 (4)	C6C—C1C—O1C—C12C	−69.0 (5)
C6A—C1A—O1A—C12A	−68.2 (5)	C2C—C1C—O1C—C12C	115.1 (4)
C1A—O1A—C12A—C13A	−107.7 (4)	C1C—O1C—C12C—C13C	−95.5 (4)
O1A—C12A—C13A—O13A	−15.8 (7)	O1C—C12C—C13C—O13C	−7.8 (7)
O1A—C12A—C13A—O14A	164.5 (4)	O1C—C12C—C13C—O14C	172.4 (4)
O13A—C13A—O14A—C15A	1.9 (7)	O13C—C13C—O14C—C15C	−2.6 (9)
C12A—C13A—O14A—C15A	−178.3 (4)	C12C—C13C—O14C—C15C	177.2 (5)
C13A—O14A—C15A—C16A	170.6 (4)	C13C—O14C—C15C—C16C	−83.0 (8)
O1B—C1B—C2B—C3B	179.8 (4)	O1D—C1D—C2D—C3D	−177.0 (4)
C6B—C1B—C2B—C3B	−1.2 (6)	C6D—C1D—C2D—C3D	2.7 (6)
O1B—C1B—C2B—C7B	4.1 (5)	O1D—C1D—C2D—C7D	4.5 (5)
C6B—C1B—C2B—C7B	−176.9 (4)	C6D—C1D—C2D—C7D	−175.7 (4)
C1B—C2B—C3B—C4B	−0.7 (6)	C1D—C2D—C3D—C4D	−2.1 (7)
C7B—C2B—C3B—C4B	175.0 (4)	C7D—C2D—C3D—C4D	176.4 (4)
C2B—C3B—C4B—C5B	1.5 (6)	C2D—C3D—C4D—C5D	0.2 (7)
C2B—C3B—C4B—C8B	−177.3 (4)	C2D—C3D—C4D—C8D	178.6 (4)
C3B—C4B—C5B—C6B	−0.4 (6)	C3D—C4D—C5D—C6D	1.0 (7)
C8B—C4B—C5B—C6B	178.5 (4)	C8D—C4D—C5D—C6D	−177.3 (5)
C4B—C5B—C6B—C1B	−1.4 (6)	O1D—C1D—C6D—C5D	178.2 (4)
C4B—C5B—C6B—C7C	−179.5 (4)	C2D—C1D—C6D—C5D	−1.6 (6)
O1B—C1B—C6B—C5B	−178.8 (4)	O1D—C1D—C6D—C7A	−2.4 (6)
C2B—C1B—C6B—C5B	2.3 (6)	C2D—C1D—C6D—C7A	177.8 (4)
O1B—C1B—C6B—C7C	−0.8 (6)	C4D—C5D—C6D—C1D	−0.3 (7)
C2B—C1B—C6B—C7C	−179.8 (4)	C4D—C5D—C6D—C7A	−179.7 (4)
C1A—C6A—C7B—C2B	−98.1 (4)	C2A—C7A—C6D—C1D	−83.7 (5)
C5A—C6A—C7B—C2B	76.5 (5)	C2A—C7A—C6D—C5D	95.7 (5)
C3B—C2B—C7B—C6A	−84.4 (5)	C3D—C2D—C7D—C6C	−88.1 (5)
C1B—C2B—C7B—C6A	91.3 (5)	C1D—C2D—C7D—C6C	90.4 (4)
C3B—C4B—C8B—C10B	117.1 (5)	C1C—C6C—C7D—C2D	−104.5 (4)
C5B—C4B—C8B—C10B	−61.7 (5)	C5C—C6C—C7D—C2D	72.3 (5)
C3B—C4B—C8B—C11B	−1.7 (6)	C3D—C4D—C8D—C9D	177.0 (6)
C5B—C4B—C8B—C11B	179.5 (4)	C5D—C4D—C8D—C9D	−4.8 (9)
C3B—C4B—C8B—C9B	−123.2 (5)	C3D—C4D—C8D—C11D	−60.0 (7)
C5B—C4B—C8B—C9B	58.0 (5)	C5D—C4D—C8D—C11D	118.2 (6)
C6C—C1C—C2C—C3C	6.2 (6)	C3D—C4D—C8D—C10D	55.3 (7)
O1C—C1C—C2C—C3C	−177.9 (3)	C5D—C4D—C8D—C10D	−126.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1D—H1D···O1A	0.84	1.89	2.722 (4)	168
O1B—H1B···O1C	0.84	1.94	2.777 (4)	171