Crystal structure of (1S,3R,8R,9R,10S)-2,4,6-tris­(2,2-di­chloro-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.0^1,3]dodec-9-yl)cyclo­triboroxane

The title compound accounts among the rare essential oil of the Atlas cedar (Cedrus Atlantica) derivatives, in which three fused-ring systems surround a hexa­gonal heterocyclic ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.050
• wR factor = 0.121
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT222_ALERT_3_C Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        4.1 Ratio
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C39 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0061 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report

Alert level G
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT791_ALERT_4_G The Model has Chirality at C1      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C3      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C8      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C9      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C10     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C17     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C19     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C24     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C25     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C26     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C33     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C35     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C40     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C41     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C42     (Chiral SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          1 Report

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  19 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

(1S,3R,8R,9R,10S)-2,4,6-Tris(2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-yl)cyclotriboroxane

Crystal data

C48H75B3Cl6O3	Dx = 1.263 Mg m^−3
Mr = 945.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 10143 reflections
a = 8.8240 (2) Å	θ = 1.5–26.4°
b = 21.1340 (4) Å	µ = 0.39 mm^−1
c = 26.6620 (7) Å	T = 293 K
V = 4972.1 (2) Å^3	Box, colourless
Z = 4	0.45 × 0.35 × 0.30 mm
F(000) = 2016

Data collection

Bruker APEXII CCD diffractometer	10143 independent reflections
Radiation source: fine-focus sealed tube	9010 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω and φ scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→10
Tmin = 0.642, Tmax = 0.746	k = −26→26
43691 measured reflections	l = −33→26

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 1.8134P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.121	(Δ/σ)max < 0.001
S = 1.15	Δρmax = 0.30 e Å^−3
10143 reflections	Δρmin = −0.21 e Å^−3
553 parameters	Absolute structure: Flack x determined using 3616 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons & Flack, 2004)
0 restraints	Absolute structure parameter: 0.021 (16)

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.

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

	x	y	z	Uiso*/Ueq
C1	0.6458 (4)	0.17458 (16)	0.21900 (14)	0.0313 (8)
C2	0.5394 (5)	0.22780 (19)	0.20422 (16)	0.0397 (9)
C3	0.4910 (5)	0.1825 (2)	0.24487 (18)	0.0469 (10)
C4	0.4921 (6)	0.2048 (3)	0.29887 (19)	0.0653 (14)
H4A	0.3889	0.2140	0.3091	0.078*
H4B	0.5497	0.2438	0.3010	0.078*
C5	0.5599 (8)	0.1565 (3)	0.3353 (2)	0.0800 (18)
H5A	0.6040	0.1793	0.3633	0.096*
H5B	0.4782	0.1307	0.3485	0.096*
C6	0.6803 (7)	0.1128 (3)	0.3135 (2)	0.0745 (18)
H6A	0.6315	0.0871	0.2880	0.089*
H6B	0.7114	0.0842	0.3401	0.089*
C7	0.8262 (6)	0.1404 (2)	0.29000 (17)	0.0494 (11)
C8	0.7871 (4)	0.19135 (16)	0.24919 (13)	0.0307 (7)
H8	0.7609	0.2298	0.2679	0.037*
C9	0.9183 (4)	0.21114 (15)	0.21272 (13)	0.0288 (7)
H9	1.0088	0.1879	0.2234	0.035*
C10	0.8896 (4)	0.19320 (17)	0.15719 (14)	0.0333 (8)
H10	0.8174	0.2237	0.1432	0.040*
C11	0.8190 (5)	0.12724 (18)	0.15311 (17)	0.0434 (10)
H11A	0.8899	0.0963	0.1663	0.052*
H11B	0.8022	0.1174	0.1180	0.052*
C12	0.6687 (5)	0.12144 (18)	0.18142 (17)	0.0403 (9)
H12A	0.5859	0.1218	0.1575	0.048*
H12B	0.6661	0.0812	0.1989	0.048*
C13	0.3635 (6)	0.1357 (3)	0.2337 (2)	0.0703 (16)
H13A	0.2678	0.1547	0.2418	0.106*
H13B	0.3774	0.0982	0.2534	0.106*
H13C	0.3652	0.1249	0.1987	0.106*
C14	0.9222 (7)	0.1727 (3)	0.3306 (2)	0.0724 (17)
H14A	0.9381	0.1439	0.3579	0.109*
H14B	0.8702	0.2097	0.3426	0.109*
H14C	1.0182	0.1849	0.3167	0.109*
C15	0.9206 (7)	0.0842 (2)	0.2702 (2)	0.0685 (16)
H15A	1.0110	0.0998	0.2544	0.103*
H15B	0.8620	0.0608	0.2463	0.103*
H15C	0.9477	0.0571	0.2977	0.103*
C16	1.0343 (5)	0.1964 (2)	0.12609 (18)	0.0506 (11)
H16A	1.1059	0.1661	0.1386	0.076*
H16B	1.0767	0.2381	0.1284	0.076*
H16C	1.0112	0.1871	0.0917	0.076*
C17	0.9294 (4)	0.42656 (16)	0.04345 (13)	0.0312 (8)
C18	0.8094 (5)	0.38548 (19)	0.01951 (15)	0.0404 (9)
C19	0.9552 (5)	0.39423 (19)	−0.00776 (14)	0.0394 (9)
C20	1.0644 (6)	0.3389 (2)	−0.01189 (16)	0.0523 (12)
H20A	1.0335	0.3064	0.0116	0.063*
H20B	1.0570	0.3213	−0.0454	0.063*
C21	1.2269 (6)	0.3558 (2)	−0.00178 (17)	0.0534 (12)
H21A	1.2479	0.3970	−0.0162	0.064*
H21B	1.2918	0.3252	−0.0184	0.064*
C22	1.2659 (5)	0.3573 (2)	0.05369 (17)	0.0486 (10)
H22A	1.3752	0.3609	0.0566	0.058*
H22B	1.2376	0.3167	0.0679	0.058*
C23	1.1945 (4)	0.40950 (18)	0.08649 (15)	0.0358 (8)
C24	1.0157 (4)	0.40283 (15)	0.08946 (13)	0.0274 (7)
H24	0.9944	0.3574	0.0920	0.033*
C25	0.9490 (4)	0.43399 (15)	0.13811 (13)	0.0276 (7)
H25	1.0079	0.4723	0.1450	0.033*
C26	0.7824 (5)	0.45404 (17)	0.13025 (14)	0.0364 (8)
H26	0.7269	0.4176	0.1169	0.044*
C27	0.7765 (6)	0.50710 (19)	0.09091 (16)	0.0471 (10)
H27A	0.6744	0.5099	0.0776	0.056*
H27B	0.7996	0.5471	0.1070	0.056*
C28	0.8875 (5)	0.49659 (17)	0.04761 (15)	0.0417 (10)
H28A	0.8417	0.5106	0.0165	0.050*
H28B	0.9784	0.5214	0.0532	0.050*
C29	0.9548 (7)	0.4343 (3)	−0.05569 (16)	0.0610 (13)
H29A	0.9150	0.4097	−0.0830	0.092*
H29B	1.0565	0.4472	−0.0634	0.092*
H29C	0.8927	0.4711	−0.0507	0.092*
C30	1.2650 (5)	0.4002 (2)	0.13888 (17)	0.0521 (11)
H30A	1.3735	0.4016	0.1363	0.078*
H30B	1.2346	0.3599	0.1521	0.078*
H30C	1.2309	0.4333	0.1608	0.078*
C31	1.2463 (6)	0.4746 (2)	0.06746 (18)	0.0523 (11)
H31A	1.2123	0.5068	0.0902	0.078*
H31B	1.2042	0.4822	0.0348	0.078*
H31C	1.3549	0.4755	0.0655	0.078*
C32	0.7037 (5)	0.4753 (2)	0.17845 (17)	0.0507 (11)
H32A	0.7632	0.5076	0.1944	0.076*
H32B	0.6932	0.4398	0.2007	0.076*
H32C	0.6053	0.4919	0.1705	0.076*
C33	1.0967 (5)	0.38232 (17)	0.41633 (14)	0.0353 (9)
C34	1.1939 (5)	0.32888 (19)	0.43607 (16)	0.0456 (10)
C35	1.0573 (6)	0.3474 (2)	0.46558 (14)	0.0454 (10)
C36	0.9216 (6)	0.3042 (2)	0.46380 (18)	0.0568 (12)
H36A	0.9243	0.2762	0.4926	0.068*
H36B	0.9275	0.2783	0.4338	0.068*
C37	0.7722 (7)	0.3398 (3)	0.4637 (2)	0.0724 (15)
H37A	0.7459	0.3505	0.4980	0.087*
H37B	0.6937	0.3121	0.4508	0.087*
C38	0.7744 (7)	0.4012 (3)	0.4321 (2)	0.0658 (14)
H38A	0.6730	0.4189	0.4324	0.079*
H38B	0.8405	0.4312	0.4487	0.079*
C39	0.8254 (5)	0.3957 (2)	0.37709 (17)	0.0490 (11)
C40	0.9966 (4)	0.37246 (17)	0.36994 (13)	0.0321 (8)
H40	0.9923	0.3267	0.3640	0.039*
C41	1.0726 (5)	0.40213 (17)	0.32324 (14)	0.0365 (9)
H41	1.0393	0.4464	0.3223	0.044*
C42	1.2457 (5)	0.40393 (19)	0.32941 (15)	0.0404 (9)
H42	1.2800	0.3617	0.3394	0.049*
C43	1.2839 (5)	0.45050 (19)	0.37214 (15)	0.0433 (10)
H43A	1.3846	0.4411	0.3847	0.052*
H43B	1.2853	0.4932	0.3588	0.052*
C44	1.1710 (5)	0.44758 (18)	0.41581 (15)	0.0428 (10)
H44A	1.2234	0.4549	0.4473	0.051*
H44B	1.0944	0.4801	0.4118	0.051*
C45	1.0765 (9)	0.3794 (3)	0.51637 (17)	0.0756 (17)
H45A	1.0813	0.3478	0.5422	0.113*
H45B	0.9918	0.4069	0.5225	0.113*
H45C	1.1684	0.4037	0.5165	0.113*
C46	0.7942 (8)	0.4625 (3)	0.3550 (2)	0.0820 (18)
H46A	0.8149	0.4623	0.3196	0.123*
H46B	0.8584	0.4930	0.3712	0.123*
H46C	0.6900	0.4736	0.3605	0.123*
C47	0.7213 (7)	0.3509 (3)	0.3493 (3)	0.089 (2)
H47A	0.7361	0.3086	0.3616	0.134*
H47B	0.7438	0.3523	0.3141	0.134*
H47C	0.6179	0.3633	0.3547	0.134*
C48	1.3317 (5)	0.4233 (2)	0.28164 (17)	0.0483 (10)
H48A	1.3167	0.3918	0.2562	0.072*
H48B	1.4379	0.4268	0.2890	0.072*
H48C	1.2943	0.4633	0.2699	0.072*
B1	0.9557 (5)	0.28394 (19)	0.21886 (16)	0.0292 (8)
B2	0.9659 (5)	0.38880 (19)	0.18473 (15)	0.0301 (8)
B3	1.0240 (5)	0.3724 (2)	0.27155 (16)	0.0333 (9)
Cl1	0.58414 (13)	0.30741 (5)	0.21868 (5)	0.0522 (3)
Cl2	0.44704 (14)	0.22716 (6)	0.14578 (5)	0.0591 (3)
Cl3	0.75804 (16)	0.31161 (5)	0.04581 (5)	0.0609 (3)
Cl4	0.64161 (15)	0.42021 (7)	−0.00517 (5)	0.0652 (4)
Cl5	1.20362 (16)	0.25460 (5)	0.40531 (5)	0.0612 (3)
Cl6	1.37512 (16)	0.34621 (7)	0.46075 (6)	0.0753 (4)
O1	0.9416 (3)	0.32509 (11)	0.17941 (9)	0.0329 (6)
O2	0.9998 (3)	0.41195 (11)	0.23161 (9)	0.0378 (6)
O3	1.0025 (3)	0.30796 (12)	0.26456 (9)	0.0357 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0350 (18)	0.0271 (16)	0.0318 (19)	−0.0024 (14)	−0.0014 (16)	0.0026 (15)
C2	0.040 (2)	0.039 (2)	0.040 (2)	0.0052 (18)	−0.0045 (18)	−0.0032 (17)
C3	0.041 (2)	0.053 (3)	0.046 (2)	−0.006 (2)	0.0063 (19)	0.004 (2)
C4	0.063 (3)	0.084 (4)	0.049 (3)	−0.010 (3)	0.020 (2)	0.001 (3)
C5	0.089 (4)	0.104 (5)	0.046 (3)	−0.026 (4)	0.015 (3)	0.015 (3)
C6	0.096 (4)	0.069 (3)	0.058 (3)	−0.025 (3)	−0.015 (3)	0.039 (3)
C7	0.063 (3)	0.038 (2)	0.047 (3)	−0.010 (2)	−0.019 (2)	0.0199 (19)
C8	0.0390 (19)	0.0246 (15)	0.0286 (18)	−0.0019 (15)	−0.0057 (16)	0.0038 (14)
C9	0.0328 (17)	0.0244 (15)	0.0292 (18)	0.0039 (14)	−0.0050 (15)	0.0013 (14)
C10	0.041 (2)	0.0279 (17)	0.0308 (19)	0.0005 (16)	−0.0015 (16)	−0.0029 (15)
C11	0.053 (2)	0.0308 (19)	0.046 (2)	0.0025 (18)	−0.006 (2)	−0.0127 (18)
C12	0.045 (2)	0.0289 (18)	0.047 (2)	−0.0047 (17)	−0.0117 (19)	−0.0057 (17)
C13	0.043 (3)	0.085 (4)	0.083 (4)	−0.021 (3)	0.002 (3)	0.014 (3)
C14	0.098 (4)	0.066 (3)	0.053 (3)	−0.021 (3)	−0.041 (3)	0.025 (3)
C15	0.078 (3)	0.035 (2)	0.093 (4)	0.003 (2)	−0.033 (3)	0.026 (2)
C16	0.049 (2)	0.054 (3)	0.049 (3)	−0.004 (2)	0.009 (2)	−0.014 (2)
C17	0.043 (2)	0.0284 (16)	0.0221 (17)	0.0018 (16)	0.0008 (16)	0.0027 (14)
C18	0.049 (2)	0.039 (2)	0.033 (2)	−0.0036 (18)	−0.0062 (18)	0.0001 (17)
C19	0.057 (3)	0.040 (2)	0.0213 (18)	−0.0003 (19)	−0.0012 (18)	−0.0020 (16)
C20	0.082 (3)	0.043 (2)	0.032 (2)	0.007 (2)	0.003 (2)	−0.0087 (18)
C21	0.069 (3)	0.049 (2)	0.042 (2)	0.014 (2)	0.022 (2)	−0.002 (2)
C22	0.044 (2)	0.048 (2)	0.054 (3)	0.009 (2)	0.010 (2)	0.007 (2)
C23	0.037 (2)	0.0383 (19)	0.033 (2)	−0.0016 (16)	0.0028 (16)	0.0042 (16)
C24	0.0388 (19)	0.0206 (15)	0.0229 (17)	−0.0011 (14)	0.0014 (15)	0.0025 (13)
C25	0.0398 (19)	0.0204 (15)	0.0227 (17)	−0.0044 (14)	−0.0011 (15)	−0.0025 (13)
C26	0.044 (2)	0.0324 (18)	0.033 (2)	0.0034 (16)	−0.0004 (18)	−0.0036 (15)
C27	0.062 (3)	0.039 (2)	0.040 (2)	0.019 (2)	−0.002 (2)	0.0024 (18)
C28	0.064 (3)	0.0281 (17)	0.033 (2)	0.0033 (18)	−0.005 (2)	0.0076 (16)
C29	0.081 (3)	0.073 (3)	0.028 (2)	0.013 (3)	0.004 (2)	0.008 (2)
C30	0.040 (2)	0.071 (3)	0.046 (3)	−0.002 (2)	−0.004 (2)	0.009 (2)
C31	0.054 (3)	0.050 (2)	0.053 (3)	−0.013 (2)	0.010 (2)	0.004 (2)
C32	0.053 (3)	0.053 (2)	0.046 (3)	0.012 (2)	0.008 (2)	−0.005 (2)
C33	0.050 (2)	0.0326 (18)	0.0231 (18)	−0.0048 (17)	−0.0034 (17)	−0.0001 (15)
C34	0.060 (3)	0.040 (2)	0.037 (2)	−0.0062 (19)	−0.013 (2)	0.0118 (18)
C35	0.070 (3)	0.045 (2)	0.0215 (19)	−0.009 (2)	−0.003 (2)	0.0054 (17)
C36	0.079 (3)	0.051 (2)	0.040 (2)	−0.012 (3)	0.010 (2)	0.009 (2)
C37	0.071 (3)	0.084 (4)	0.063 (3)	−0.012 (3)	0.021 (3)	0.007 (3)
C38	0.063 (3)	0.072 (3)	0.063 (3)	0.006 (3)	0.006 (3)	−0.011 (3)
C39	0.051 (3)	0.055 (3)	0.041 (2)	0.007 (2)	−0.004 (2)	−0.010 (2)
C40	0.043 (2)	0.0307 (17)	0.0225 (17)	−0.0037 (16)	−0.0021 (16)	−0.0042 (14)
C41	0.055 (2)	0.0300 (18)	0.0245 (18)	−0.0049 (17)	−0.0044 (18)	0.0004 (15)
C42	0.049 (2)	0.037 (2)	0.035 (2)	−0.0001 (18)	−0.0038 (18)	0.0048 (17)
C43	0.056 (3)	0.038 (2)	0.036 (2)	−0.0143 (19)	−0.008 (2)	0.0030 (17)
C44	0.066 (3)	0.034 (2)	0.028 (2)	−0.0109 (19)	−0.012 (2)	−0.0030 (16)
C45	0.118 (5)	0.084 (4)	0.025 (2)	−0.022 (4)	−0.004 (3)	0.000 (2)
C46	0.083 (4)	0.078 (4)	0.085 (4)	0.035 (3)	0.011 (4)	0.011 (3)
C47	0.054 (3)	0.117 (5)	0.098 (5)	0.006 (3)	−0.014 (3)	−0.054 (4)
C48	0.046 (2)	0.059 (3)	0.039 (2)	0.002 (2)	0.003 (2)	0.004 (2)
B1	0.031 (2)	0.0294 (18)	0.027 (2)	−0.0029 (16)	0.0009 (17)	0.0008 (16)
B2	0.039 (2)	0.0293 (19)	0.0225 (19)	−0.0029 (17)	−0.0002 (17)	−0.0015 (16)
B3	0.041 (2)	0.033 (2)	0.026 (2)	−0.0043 (18)	−0.0042 (18)	−0.0004 (17)
Cl1	0.0580 (6)	0.0354 (5)	0.0632 (7)	0.0129 (5)	−0.0028 (6)	−0.0066 (5)
Cl2	0.0518 (6)	0.0700 (7)	0.0555 (7)	0.0085 (6)	−0.0222 (6)	0.0032 (6)
Cl3	0.0764 (8)	0.0435 (5)	0.0629 (7)	−0.0235 (6)	−0.0024 (6)	−0.0012 (5)
Cl4	0.0557 (7)	0.0844 (9)	0.0557 (7)	0.0024 (6)	−0.0206 (6)	0.0005 (7)
Cl5	0.0801 (9)	0.0399 (5)	0.0637 (7)	0.0109 (6)	−0.0055 (7)	0.0077 (5)
Cl6	0.0662 (8)	0.0823 (9)	0.0772 (9)	−0.0134 (7)	−0.0370 (7)	0.0323 (8)
O1	0.0496 (15)	0.0270 (12)	0.0220 (12)	−0.0050 (11)	−0.0058 (12)	0.0006 (10)
O2	0.0651 (18)	0.0259 (12)	0.0226 (13)	−0.0054 (12)	−0.0041 (12)	−0.0008 (10)
O3	0.0556 (16)	0.0276 (12)	0.0240 (13)	−0.0053 (12)	−0.0076 (12)	0.0035 (10)

Geometric parameters (Å, º)

C1—C2	1.517 (5)	C26—C32	1.529 (6)
C1—C12	1.519 (5)	C26—C27	1.536 (6)
C1—C8	1.526 (5)	C26—H26	0.9800
C1—C3	1.540 (6)	C27—C28	1.531 (6)
C2—C3	1.508 (6)	C27—H27A	0.9700
C2—Cl2	1.758 (4)	C27—H27B	0.9700
C2—Cl1	1.771 (4)	C28—H28A	0.9700
C3—C4	1.515 (7)	C28—H28B	0.9700
C3—C13	1.527 (7)	C29—H29A	0.9600
C4—C5	1.531 (8)	C29—H29B	0.9600
C4—H4A	0.9700	C29—H29C	0.9600
C4—H4B	0.9700	C30—H30A	0.9600
C5—C6	1.523 (9)	C30—H30B	0.9600
C5—H5A	0.9700	C30—H30C	0.9600
C5—H5B	0.9700	C31—H31A	0.9600
C6—C7	1.547 (7)	C31—H31B	0.9600
C6—H6A	0.9700	C31—H31C	0.9600
C6—H6B	0.9700	C32—H32A	0.9600
C7—C14	1.535 (7)	C32—H32B	0.9600
C7—C15	1.544 (7)	C32—H32C	0.9600
C7—C8	1.569 (5)	C33—C34	1.513 (6)
C8—C9	1.569 (5)	C33—C44	1.527 (5)
C8—H8	0.9800	C33—C40	1.534 (5)
C9—C10	1.549 (5)	C33—C35	1.545 (5)
C9—B1	1.582 (5)	C34—C35	1.492 (7)
C9—H9	0.9800	C34—Cl6	1.768 (5)
C10—C16	1.524 (6)	C34—Cl5	1.773 (4)
C10—C11	1.530 (5)	C35—C36	1.507 (7)
C10—H10	0.9800	C35—C45	1.523 (6)
C11—C12	1.532 (6)	C36—C37	1.518 (8)
C11—H11A	0.9700	C36—H36A	0.9700
C11—H11B	0.9700	C36—H36B	0.9700
C12—H12A	0.9700	C37—C38	1.547 (8)
C12—H12B	0.9700	C37—H37A	0.9700
C13—H13A	0.9600	C37—H37B	0.9700
C13—H13B	0.9600	C38—C39	1.538 (7)
C13—H13C	0.9600	C38—H38A	0.9700
C14—H14A	0.9600	C38—H38B	0.9700
C14—H14B	0.9600	C39—C47	1.513 (7)
C14—H14C	0.9600	C39—C46	1.554 (7)
C15—H15A	0.9600	C39—C40	1.600 (6)
C15—H15B	0.9600	C40—C41	1.547 (5)
C15—H15C	0.9600	C40—H40	0.9800
C16—H16A	0.9600	C41—C42	1.536 (6)
C16—H16B	0.9600	C41—B3	1.575 (5)
C16—H16C	0.9600	C41—H41	0.9800
C17—C18	1.511 (5)	C42—C48	1.538 (6)
C17—C24	1.529 (5)	C42—C43	1.543 (6)
C17—C28	1.529 (5)	C42—H42	0.9800
C17—C19	1.544 (5)	C43—C44	1.533 (6)
C18—C19	1.489 (6)	C43—H43A	0.9700
C18—Cl3	1.770 (4)	C43—H43B	0.9700
C18—Cl4	1.779 (4)	C44—H44A	0.9700
C19—C20	1.518 (6)	C44—H44B	0.9700
C19—C29	1.533 (6)	C45—H45A	0.9600
C20—C21	1.502 (7)	C45—H45B	0.9600
C20—H20A	0.9700	C45—H45C	0.9600
C20—H20B	0.9700	C46—H46A	0.9600
C21—C22	1.519 (7)	C46—H46B	0.9600
C21—H21A	0.9700	C46—H46C	0.9600
C21—H21B	0.9700	C47—H47A	0.9600
C22—C23	1.543 (6)	C47—H47B	0.9600
C22—H22A	0.9700	C47—H47C	0.9600
C22—H22B	0.9700	C48—H48A	0.9600
C23—C31	1.537 (6)	C48—H48B	0.9600
C23—C30	1.542 (6)	C48—H48C	0.9600
C23—C24	1.586 (5)	B1—O1	1.370 (5)
C24—C25	1.569 (5)	B1—O3	1.383 (5)
C24—H24	0.9800	B2—O1	1.371 (5)
C25—C26	1.544 (5)	B2—O2	1.375 (5)
C25—B2	1.574 (5)	B3—O2	1.371 (5)
C25—H25	0.9800	B3—O3	1.387 (5)
C2—C1—C12	117.3 (3)	C32—C26—C27	110.1 (3)
C2—C1—C8	118.1 (3)	C32—C26—C25	113.5 (3)
C12—C1—C8	114.3 (3)	C27—C26—C25	109.0 (3)
C2—C1—C3	59.1 (3)	C32—C26—H26	108.0
C12—C1—C3	119.6 (3)	C27—C26—H26	108.0
C8—C1—C3	117.6 (3)	C25—C26—H26	108.0
C3—C2—C1	61.2 (3)	C28—C27—C26	112.8 (3)
C3—C2—Cl2	120.0 (3)	C28—C27—H27A	109.0
C1—C2—Cl2	120.7 (3)	C26—C27—H27A	109.0
C3—C2—Cl1	120.6 (3)	C28—C27—H27B	109.0
C1—C2—Cl1	120.7 (3)	C26—C27—H27B	109.0
Cl2—C2—Cl1	107.7 (2)	H27A—C27—H27B	107.8
C2—C3—C4	119.0 (4)	C17—C28—C27	110.5 (3)
C2—C3—C13	118.6 (4)	C17—C28—H28A	109.6
C4—C3—C13	113.1 (4)	C27—C28—H28A	109.6
C2—C3—C1	59.7 (3)	C17—C28—H28B	109.6
C4—C3—C1	117.0 (4)	C27—C28—H28B	109.6
C13—C3—C1	119.7 (4)	H28A—C28—H28B	108.1
C3—C4—C5	113.5 (5)	C19—C29—H29A	109.5
C3—C4—H4A	108.9	C19—C29—H29B	109.5
C5—C4—H4A	108.9	H29A—C29—H29B	109.5
C3—C4—H4B	108.9	C19—C29—H29C	109.5
C5—C4—H4B	108.9	H29A—C29—H29C	109.5
H4A—C4—H4B	107.7	H29B—C29—H29C	109.5
C6—C5—C4	115.8 (4)	C23—C30—H30A	109.5
C6—C5—H5A	108.3	C23—C30—H30B	109.5
C4—C5—H5A	108.3	H30A—C30—H30B	109.5
C6—C5—H5B	108.3	C23—C30—H30C	109.5
C4—C5—H5B	108.3	H30A—C30—H30C	109.5
H5A—C5—H5B	107.4	H30B—C30—H30C	109.5
C5—C6—C7	120.4 (5)	C23—C31—H31A	109.5
C5—C6—H6A	107.2	C23—C31—H31B	109.5
C7—C6—H6A	107.2	H31A—C31—H31B	109.5
C5—C6—H6B	107.2	C23—C31—H31C	109.5
C7—C6—H6B	107.2	H31A—C31—H31C	109.5
H6A—C6—H6B	106.9	H31B—C31—H31C	109.5
C14—C7—C15	106.6 (4)	C26—C32—H32A	109.5
C14—C7—C6	109.9 (5)	C26—C32—H32B	109.5
C15—C7—C6	107.3 (4)	H32A—C32—H32B	109.5
C14—C7—C8	107.8 (3)	C26—C32—H32C	109.5
C15—C7—C8	114.2 (4)	H32A—C32—H32C	109.5
C6—C7—C8	110.9 (4)	H32B—C32—H32C	109.5
C1—C8—C9	109.8 (3)	C34—C33—C44	115.7 (4)
C1—C8—C7	112.7 (3)	C34—C33—C40	120.4 (3)
C9—C8—C7	116.8 (3)	C44—C33—C40	111.3 (3)
C1—C8—H8	105.5	C34—C33—C35	58.4 (3)
C9—C8—H8	105.5	C44—C33—C35	122.3 (3)
C7—C8—H8	105.5	C40—C33—C35	119.4 (3)
C10—C9—C8	114.0 (3)	C35—C34—C33	61.9 (3)
C10—C9—B1	111.8 (3)	C35—C34—Cl6	118.7 (3)
C8—C9—B1	110.4 (3)	C33—C34—Cl6	119.2 (3)
C10—C9—H9	106.7	C35—C34—Cl5	121.1 (3)
C8—C9—H9	106.7	C33—C34—Cl5	121.8 (3)
B1—C9—H9	106.7	Cl6—C34—Cl5	108.2 (3)
C16—C10—C11	110.1 (3)	C34—C35—C36	117.8 (4)
C16—C10—C9	111.8 (3)	C34—C35—C45	119.7 (5)
C11—C10—C9	111.0 (3)	C36—C35—C45	112.7 (4)
C16—C10—H10	108.0	C34—C35—C33	59.7 (3)
C11—C10—H10	108.0	C36—C35—C33	116.2 (3)
C9—C10—H10	108.0	C45—C35—C33	121.3 (4)
C10—C11—C12	113.0 (3)	C35—C36—C37	112.9 (4)
C10—C11—H11A	109.0	C35—C36—H36A	109.0
C12—C11—H11A	109.0	C37—C36—H36A	109.0
C10—C11—H11B	109.0	C35—C36—H36B	109.0
C12—C11—H11B	109.0	C37—C36—H36B	109.0
H11A—C11—H11B	107.8	H36A—C36—H36B	107.8
C1—C12—C11	112.4 (3)	C36—C37—C38	113.9 (4)
C1—C12—H12A	109.1	C36—C37—H37A	108.8
C11—C12—H12A	109.1	C38—C37—H37A	108.8
C1—C12—H12B	109.1	C36—C37—H37B	108.8
C11—C12—H12B	109.1	C38—C37—H37B	108.8
H12A—C12—H12B	107.9	H37A—C37—H37B	107.7
C3—C13—H13A	109.5	C39—C38—C37	117.4 (5)
C3—C13—H13B	109.5	C39—C38—H38A	107.9
H13A—C13—H13B	109.5	C37—C38—H38A	107.9
C3—C13—H13C	109.5	C39—C38—H38B	107.9
H13A—C13—H13C	109.5	C37—C38—H38B	107.9
H13B—C13—H13C	109.5	H38A—C38—H38B	107.2
C7—C14—H14A	109.5	C47—C39—C38	109.6 (5)
C7—C14—H14B	109.5	C47—C39—C46	106.0 (5)
H14A—C14—H14B	109.5	C38—C39—C46	104.0 (4)
C7—C14—H14C	109.5	C47—C39—C40	108.8 (4)
H14A—C14—H14C	109.5	C38—C39—C40	114.4 (4)
H14B—C14—H14C	109.5	C46—C39—C40	113.7 (4)
C7—C15—H15A	109.5	C33—C40—C41	110.1 (3)
C7—C15—H15B	109.5	C33—C40—C39	113.9 (3)
H15A—C15—H15B	109.5	C41—C40—C39	112.4 (3)
C7—C15—H15C	109.5	C33—C40—H40	106.6
H15A—C15—H15C	109.5	C41—C40—H40	106.6
H15B—C15—H15C	109.5	C39—C40—H40	106.6
C10—C16—H16A	109.5	C42—C41—C40	110.8 (3)
C10—C16—H16B	109.5	C42—C41—B3	112.0 (3)
H16A—C16—H16B	109.5	C40—C41—B3	115.1 (3)
C10—C16—H16C	109.5	C42—C41—H41	106.1
H16A—C16—H16C	109.5	C40—C41—H41	106.1
H16B—C16—H16C	109.5	B3—C41—H41	106.1
C18—C17—C24	120.0 (3)	C41—C42—C48	114.1 (3)
C18—C17—C28	114.7 (3)	C41—C42—C43	108.2 (3)
C24—C17—C28	112.3 (3)	C48—C42—C43	109.5 (3)
C18—C17—C19	58.4 (3)	C41—C42—H42	108.3
C24—C17—C19	119.4 (3)	C48—C42—H42	108.3
C28—C17—C19	121.9 (3)	C43—C42—H42	108.3
C19—C18—C17	61.9 (3)	C44—C43—C42	113.1 (3)
C19—C18—Cl3	121.6 (3)	C44—C43—H43A	109.0
C17—C18—Cl3	121.3 (3)	C42—C43—H43A	109.0
C19—C18—Cl4	119.2 (3)	C44—C43—H43B	109.0
C17—C18—Cl4	120.2 (3)	C42—C43—H43B	109.0
Cl3—C18—Cl4	107.3 (2)	H43A—C43—H43B	107.8
C18—C19—C20	119.2 (4)	C33—C44—C43	108.8 (3)
C18—C19—C29	118.3 (4)	C33—C44—H44A	109.9
C20—C19—C29	111.5 (4)	C43—C44—H44A	109.9
C18—C19—C17	59.7 (3)	C33—C44—H44B	109.9
C20—C19—C17	119.9 (3)	C43—C44—H44B	109.9
C29—C19—C17	119.5 (3)	H44A—C44—H44B	108.3
C21—C20—C19	114.2 (4)	C35—C45—H45A	109.5
C21—C20—H20A	108.7	C35—C45—H45B	109.5
C19—C20—H20A	108.7	H45A—C45—H45B	109.5
C21—C20—H20B	108.7	C35—C45—H45C	109.5
C19—C20—H20B	108.7	H45A—C45—H45C	109.5
H20A—C20—H20B	107.6	H45B—C45—H45C	109.5
C20—C21—C22	113.3 (4)	C39—C46—H46A	109.5
C20—C21—H21A	108.9	C39—C46—H46B	109.5
C22—C21—H21A	108.9	H46A—C46—H46B	109.5
C20—C21—H21B	108.9	C39—C46—H46C	109.5
C22—C21—H21B	108.9	H46A—C46—H46C	109.5
H21A—C21—H21B	107.7	H46B—C46—H46C	109.5
C21—C22—C23	118.3 (4)	C39—C47—H47A	109.5
C21—C22—H22A	107.7	C39—C47—H47B	109.5
C23—C22—H22A	107.7	H47A—C47—H47B	109.5
C21—C22—H22B	107.7	C39—C47—H47C	109.5
C23—C22—H22B	107.7	H47A—C47—H47C	109.5
H22A—C22—H22B	107.1	H47B—C47—H47C	109.5
C31—C23—C30	107.0 (4)	C42—C48—H48A	109.5
C31—C23—C22	109.4 (3)	C42—C48—H48B	109.5
C30—C23—C22	104.9 (3)	H48A—C48—H48B	109.5
C31—C23—C24	113.1 (3)	C42—C48—H48C	109.5
C30—C23—C24	110.2 (3)	H48A—C48—H48C	109.5
C22—C23—C24	111.8 (3)	H48B—C48—H48C	109.5
C17—C24—C25	109.8 (3)	O1—B1—O3	118.1 (3)
C17—C24—C23	115.2 (3)	O1—B1—C9	121.2 (3)
C25—C24—C23	112.1 (3)	O3—B1—C9	120.7 (3)
C17—C24—H24	106.3	O1—B2—O2	118.5 (3)
C25—C24—H24	106.3	O1—B2—C25	120.0 (3)
C23—C24—H24	106.3	O2—B2—C25	121.5 (3)
C26—C25—C24	111.1 (3)	O2—B3—O3	118.2 (3)
C26—C25—B2	111.3 (3)	O2—B3—C41	118.6 (3)
C24—C25—B2	111.3 (3)	O3—B3—C41	123.2 (3)
C26—C25—H25	107.7	B1—O1—B2	122.0 (3)
C24—C25—H25	107.7	B3—O2—B2	121.5 (3)
B2—C25—H25	107.7	B1—O3—B3	121.3 (3)