Dibenzoate esters of cis-tetra­lin-2,3-diol as analogs of (–)-epigallocatechin gallate: synthesis and crystal structure of anti­cancer drug candidates

(−)-Epigallocatechin gallate (EGCG), the main component of green tea extract, displays multiple biological activities. However, it cannot be used as a drug due to its low cellular absorption, instability and metabolic degradation. Therefore, there is a need to provide analogs that can overcome the limitations of EGCG. In this work, six synthetic analogs of EGCG sharing a common tetra­lindiol dibenzoate core were synthesized and fully characterized by ¹H NMR, ¹³C NMR, HRMS and IR spectroscopies, and X-ray crystallography. These are (2R,3S)-1,2,3,4-tetra­hydro­naphthalene-2,3-diyl bis­[3,4,5-tris­(benz­yloxy)benzoate], C₆₆H₅₆O₁₀, and the analogous esters bis­(3,4,5-tri­meth­oxy­benzoate), C₃₀H₃₂O₁₀, bis­(3,4,5-tri­fluoro­benzoate), C₂₄H₁₄F₆O₄, bis­[4-(benz­yloxy)benzoate], C₃₈H₃₂O₆, bis­(4-meth­oxy­benzoate), C₂₆H₂₄O₆, and bis­(2,4,6-tri­fluoro­benzoate), C₂₄H₁₄F₆O₄. Structural analysis revealed that the mol­ecular shapes of these dibenzoate esters of tetra­lindiol are significantly different from that of previously reported dimandelate esters or monobenzoate esters, as the acid moieties extend far from the bicyclic system without folding back over the tetra­lin fragment. Com­pounds with small fluorine substituents take a V-shape, whereas larger meth­oxy and benz­yloxy groups determine the formation of an L-shape or a cavity. Inter­molecular inter­actions are dominated by π–π stacking and C—H...π inter­actions involving the arene rings in the benzoate fragment and the arene ring in the tetra­hydro­naphthalene moiety. All six crystal structures are determined in centrosymmetric space groups (either P, P2₁/n, C2/c or I2/a).

Computing details

Data collection: CrystalClear (Rigaku, 2008) for (4), (6), (7), (8), (9); CrystalClear-SM Expert (Rigaku, 2011) for (5). Cell refinement: CrystalClear (Rigaku, 2008) for (4), (6), (7), (8), (9); CrystalClear-SM Expert (Rigaku, 2011) for (5). Data reduction: CrystalClear (Rigaku, 2008) for (4), (6), (7), (8), (9); CrystalClear-SM Expert (Rigaku, 2011) for (5). For all structures, program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(2R,3S)-1,2,3,4-Tetrahydronaphthalene-2,3-diyl bis[3,4,5-tris(benzyloxy)benzoate] (4)

Crystal data

C66H56O10	Z = 2
Mr = 1009.10	F(000) = 1064
Triclinic, P1	Dx = 1.249 Mg m^−3
a = 13.574 (3) Å	Mo Kα radiation, λ = 0.71075 Å
b = 13.829 (3) Å	Cell parameters from 8135 reflections
c = 14.657 (3) Å	θ = 3.0–27.5°
α = 79.013 (6)°	µ = 0.08 mm^−1
β = 87.544 (9)°	T = 193 K
γ = 83.381 (8)°	Plate, clear colourless
V = 2682.3 (10) Å^3	0.13 × 0.08 × 0.07 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	11802 independent reflections
Radiation source: sealed X-ray tube	7475 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
dtprofit.ref scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	h = −16→16
Tmin = 0.857, Tmax = 1.000	k = −17→17
22437 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.0587P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
11802 reflections	Δρmax = 0.20 e Å^−3
740 parameters	Δρmin = −0.18 e Å^−3
132 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.73344 (8)	0.70247 (9)	0.68718 (8)	0.0408 (3)
O5	0.53926 (9)	0.97432 (9)	0.36357 (8)	0.0455 (3)
O9	0.93988 (8)	0.41510 (9)	0.25621 (8)	0.0431 (3)
O6	0.83722 (9)	0.52822 (9)	0.64620 (8)	0.0438 (3)
O3	0.37480 (9)	0.75731 (9)	0.58587 (9)	0.0476 (3)
O8	0.86191 (9)	0.59140 (9)	0.29997 (8)	0.0473 (3)
O10	0.95194 (9)	0.25176 (9)	0.38016 (9)	0.0473 (3)
O4	0.37380 (9)	0.90210 (10)	0.43536 (9)	0.0503 (4)
O2	0.81809 (9)	0.75757 (10)	0.55480 (9)	0.0552 (4)
O7	0.90443 (10)	0.37088 (9)	0.69560 (9)	0.0540 (4)
C12	0.64205 (13)	0.78422 (12)	0.55684 (12)	0.0366 (4)
C16	0.54976 (13)	0.89834 (13)	0.43846 (12)	0.0375 (4)
C14	0.46598 (13)	0.78486 (13)	0.55310 (12)	0.0378 (4)
C15	0.46235 (13)	0.85937 (13)	0.47422 (12)	0.0370 (4)
C32	0.62505 (12)	1.02131 (13)	0.32988 (12)	0.0396 (4)
H32A	0.677190	0.972109	0.311392	0.048*
H32B	0.651408	1.050218	0.379390	0.048*
C2	0.71398 (13)	0.54176 (14)	0.87901 (12)	0.0412 (4)
C17	0.63958 (13)	0.85989 (13)	0.47919 (12)	0.0382 (4)
H17	0.699230	0.885111	0.454195	0.046*
C13	0.55558 (13)	0.74646 (13)	0.59436 (12)	0.0387 (4)
H13	0.557855	0.694971	0.647622	0.046*
C11	0.74048 (14)	0.74752 (13)	0.59737 (13)	0.0395 (4)
C42	0.88031 (13)	0.51315 (13)	0.37194 (12)	0.0391 (4)
C43	0.91311 (13)	0.42290 (13)	0.34640 (12)	0.0392 (4)
C41	0.86817 (12)	0.51874 (13)	0.46550 (12)	0.0397 (4)
H41	0.847318	0.580496	0.483485	0.048*
C9	0.82884 (13)	0.54594 (13)	0.74040 (12)	0.0392 (4)
H9	0.888512	0.512055	0.775744	0.047*
C1	0.75421 (13)	0.62360 (14)	0.89874 (12)	0.0407 (4)
C33	0.59738 (13)	1.10170 (13)	0.24740 (12)	0.0370 (4)
C44	0.92717 (13)	0.33670 (13)	0.41472 (13)	0.0397 (4)
C10	0.73620 (14)	0.50701 (14)	0.78790 (12)	0.0434 (4)
H10A	0.679204	0.529846	0.746345	0.052*
H10B	0.745030	0.433660	0.799434	0.052*
C40	0.88666 (12)	0.43373 (13)	0.53238 (12)	0.0380 (4)
C39	0.87865 (13)	0.43821 (14)	0.63261 (13)	0.0416 (4)
C8	0.82547 (13)	0.65648 (13)	0.73355 (13)	0.0403 (4)
H8	0.884320	0.681707	0.697256	0.048*
C19	0.40241 (13)	0.57904 (14)	0.65011 (13)	0.0438 (5)
C45	0.91520 (13)	0.34203 (13)	0.50787 (13)	0.0415 (4)
H45	0.926278	0.284038	0.554351	0.050*
C61	0.98163 (14)	0.08034 (13)	0.38786 (13)	0.0444 (5)
C34	0.50041 (14)	1.14012 (14)	0.22908 (13)	0.0464 (5)
H34	0.448357	1.114626	0.268517	0.056*
C47	0.79546 (15)	0.75641 (13)	0.23721 (13)	0.0449 (5)
C18	0.37089 (14)	0.68120 (14)	0.66778 (13)	0.0465 (5)
H18A	0.302188	0.683749	0.693469	0.056*
H18B	0.414233	0.695191	0.715236	0.056*
C38	0.67231 (14)	1.14153 (14)	0.19001 (13)	0.0441 (5)
H38	0.739440	1.115735	0.201778	0.053*
C7	0.82248 (14)	0.68111 (14)	0.82976 (13)	0.0446 (5)
H7A	0.801097	0.752783	0.824889	0.054*
H7B	0.890500	0.668216	0.854318	0.054*
C6	0.73257 (15)	0.65074 (16)	0.98476 (14)	0.0527 (5)
H6	0.760252	0.706035	0.998924	0.063*
C60	0.96534 (14)	0.15976 (13)	0.44522 (13)	0.0460 (5)
H60A	0.905811	0.150970	0.486095	0.055*
H60B	1.023403	0.157974	0.484386	0.055*
C3	0.65294 (15)	0.49063 (16)	0.94546 (14)	0.0538 (5)
H3	0.625285	0.434840	0.932358	0.065*
C5	0.67191 (16)	0.59929 (18)	1.04993 (15)	0.0621 (6)
H5	0.658013	0.619035	1.108186	0.075*
C35	0.47834 (16)	1.21551 (16)	0.15369 (15)	0.0571 (6)
H35	0.411190	1.240535	0.141004	0.069*
C37	0.65043 (16)	1.21825 (15)	0.11596 (13)	0.0519 (5)
H37	0.702470	1.246062	0.078107	0.062*
C46	0.82522 (16)	0.68509 (14)	0.32410 (14)	0.0539 (5)
H46A	0.877430	0.710401	0.355316	0.065*
H46B	0.767420	0.677151	0.367347	0.065*
C36	0.55313 (17)	1.25446 (16)	0.09699 (14)	0.0586 (6)
H36	0.537753	1.305984	0.045100	0.070*
C54	0.88872 (13)	0.36655 (15)	0.12043 (13)	0.0460 (5)
C26A	0.3268 (13)	0.8511 (13)	0.2925 (11)	0.052 (4)	0.51 (2)
C53	0.86549 (14)	0.43764 (16)	0.18628 (14)	0.0526 (5)
H53A	0.866193	0.506736	0.152447	0.063*
H53B	0.798913	0.430224	0.215313	0.063*
C24	0.36813 (15)	0.54799 (17)	0.57460 (16)	0.0593 (6)
H24	0.325199	0.592446	0.532462	0.071*
C4	0.63186 (16)	0.51924 (19)	1.02968 (15)	0.0628 (6)
H4	0.589589	0.483628	1.073848	0.075*
C59	0.90289 (15)	0.26572 (16)	0.15303 (15)	0.0553 (5)
H59	0.900312	0.241167	0.218092	0.066*
C20	0.46373 (16)	0.51275 (16)	0.71112 (16)	0.0603 (6)
H20	0.488034	0.532978	0.763544	0.072*
C66	1.07103 (16)	0.06351 (16)	0.34243 (16)	0.0632 (6)
H66	1.123294	0.101643	0.349060	0.076*
C62	0.90766 (16)	0.02384 (16)	0.37733 (16)	0.0596 (6)
H62	0.845350	0.034086	0.408067	0.071*
C58	0.92065 (16)	0.20021 (18)	0.09315 (17)	0.0643 (6)
H58	0.930273	0.130964	0.116745	0.077*
C52	0.86359 (17)	0.78305 (17)	0.16801 (15)	0.0619 (6)
H52	0.930286	0.753500	0.174210	0.074*
C25	0.31539 (16)	0.83749 (19)	0.39921 (16)	0.0687 (7)
H25A	0.244685	0.852198	0.416431	0.082*	0.51 (2)
H25B	0.336939	0.767736	0.427390	0.082*	0.51 (2)
H25C	0.335870	0.768489	0.430378	0.082*	0.49 (2)
H25D	0.245037	0.853653	0.416793	0.082*	0.49 (2)
C48	0.69896 (17)	0.79881 (17)	0.22646 (17)	0.0687 (7)
H48	0.650383	0.780212	0.273145	0.082*
C65	1.08616 (18)	−0.00778 (18)	0.28739 (18)	0.0742 (7)
H65	1.148122	−0.017859	0.256035	0.089*
C64	1.0114 (2)	−0.06416 (18)	0.27803 (18)	0.0757 (7)
H64	1.021546	−0.113934	0.240950	0.091*
C63	0.92267 (19)	−0.04776 (18)	0.32256 (19)	0.0766 (7)
H63	0.870495	−0.085994	0.315895	0.092*
C50	0.7426 (2)	0.89517 (18)	0.08043 (19)	0.0829 (8)
H50	0.725121	0.944114	0.027095	0.099*
C23	0.39563 (19)	0.4525 (2)	0.5595 (2)	0.0768 (8)
H23	0.372123	0.432234	0.506699	0.092*
C51	0.8371 (2)	0.85186 (19)	0.08964 (18)	0.0807 (8)
H51	0.885222	0.868952	0.042034	0.097*
C22	0.4562 (2)	0.3876 (2)	0.6199 (2)	0.0833 (9)
H22	0.474983	0.322286	0.609220	0.100*
C55	0.89481 (17)	0.40077 (19)	0.02617 (15)	0.0704 (7)
H55	0.886999	0.470041	0.002465	0.084*
C31A	0.3658 (14)	0.9309 (12)	0.2398 (11)	0.063 (3)	0.51 (2)
H31A	0.385684	0.980911	0.269164	0.076*	0.51 (2)
C57	0.92445 (18)	0.2350 (2)	−0.00055 (18)	0.0784 (7)
H57	0.935565	0.189737	−0.042172	0.094*
C21	0.49015 (19)	0.41673 (19)	0.6964 (2)	0.0791 (8)
H21	0.531595	0.371278	0.739166	0.095*
C49	0.6719 (2)	0.8692 (2)	0.1471 (2)	0.0881 (8)
H49	0.605274	0.898598	0.139658	0.106*
C56	0.9123 (2)	0.3346 (2)	−0.03458 (17)	0.0875 (9)
H56	0.915831	0.358599	−0.099702	0.105*
C30A	0.3771 (13)	0.9402 (11)	0.1434 (9)	0.075 (3)	0.51 (2)
H30A	0.405262	0.996010	0.108618	0.090*	0.51 (2)
C27A	0.2971 (14)	0.7812 (11)	0.2453 (10)	0.081 (4)	0.51 (2)
H27A	0.270088	0.724670	0.279913	0.097*	0.51 (2)
C28A	0.3058 (15)	0.7916 (9)	0.1490 (9)	0.093 (4)	0.51 (2)
H28A	0.282308	0.743992	0.118686	0.112*	0.51 (2)
C29A	0.3483 (12)	0.8706 (9)	0.0978 (10)	0.079 (3)	0.51 (2)
H29A	0.357499	0.876937	0.032428	0.095*	0.51 (2)
C26B	0.3215 (13)	0.8412 (13)	0.3011 (12)	0.051 (4)	0.49 (2)
C31B	0.3788 (16)	0.9023 (14)	0.2421 (11)	0.068 (4)	0.49 (2)
H31B	0.421729	0.940334	0.266418	0.081*	0.49 (2)
C27B	0.2617 (10)	0.7844 (11)	0.2661 (11)	0.065 (3)	0.49 (2)
H27B	0.223593	0.740430	0.306852	0.078*	0.49 (2)
C28B	0.2572 (13)	0.7914 (10)	0.1718 (11)	0.090 (4)	0.49 (2)
H28B	0.216189	0.751400	0.147824	0.108*	0.49 (2)
C29B	0.3101 (14)	0.8543 (14)	0.1121 (11)	0.100 (5)	0.49 (2)
H29B	0.303156	0.861116	0.046881	0.120*	0.49 (2)
C30B	0.3739 (15)	0.9083 (16)	0.1467 (11)	0.100 (5)	0.49 (2)
H30B	0.414359	0.949476	0.105491	0.120*	0.49 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0425 (7)	0.0396 (7)	0.0370 (7)	−0.0021 (6)	−0.0012 (6)	0.0001 (6)
O5	0.0440 (7)	0.0450 (8)	0.0441 (8)	−0.0155 (6)	−0.0038 (6)	0.0074 (6)
O9	0.0442 (7)	0.0450 (8)	0.0391 (7)	0.0011 (6)	−0.0015 (6)	−0.0089 (6)
O6	0.0566 (8)	0.0372 (7)	0.0355 (7)	0.0030 (6)	0.0003 (6)	−0.0068 (6)
O3	0.0449 (7)	0.0480 (8)	0.0479 (8)	−0.0125 (6)	0.0077 (6)	−0.0012 (6)
O8	0.0674 (9)	0.0292 (7)	0.0424 (8)	0.0033 (6)	0.0007 (6)	−0.0046 (6)
O10	0.0659 (9)	0.0304 (7)	0.0438 (8)	0.0034 (6)	−0.0007 (6)	−0.0077 (6)
O4	0.0454 (8)	0.0537 (9)	0.0502 (8)	−0.0100 (6)	−0.0079 (6)	−0.0017 (7)
O2	0.0461 (8)	0.0619 (10)	0.0503 (8)	−0.0072 (7)	0.0055 (7)	0.0077 (7)
O7	0.0786 (10)	0.0374 (8)	0.0426 (8)	0.0016 (7)	−0.0059 (7)	−0.0027 (6)
C12	0.0443 (11)	0.0317 (9)	0.0351 (10)	−0.0066 (8)	0.0023 (8)	−0.0085 (8)
C16	0.0504 (11)	0.0311 (9)	0.0317 (9)	−0.0106 (8)	−0.0006 (8)	−0.0038 (7)
C14	0.0424 (11)	0.0367 (10)	0.0367 (10)	−0.0117 (8)	0.0073 (8)	−0.0102 (8)
C15	0.0392 (10)	0.0358 (10)	0.0382 (10)	−0.0078 (8)	−0.0011 (8)	−0.0098 (8)
C32	0.0415 (10)	0.0346 (10)	0.0415 (10)	−0.0091 (8)	0.0022 (8)	−0.0021 (8)
C2	0.0431 (11)	0.0438 (11)	0.0351 (10)	−0.0016 (9)	−0.0046 (8)	−0.0042 (8)
C17	0.0433 (11)	0.0351 (10)	0.0367 (10)	−0.0107 (8)	0.0018 (8)	−0.0047 (8)
C13	0.0493 (11)	0.0313 (9)	0.0355 (10)	−0.0075 (8)	0.0028 (9)	−0.0050 (8)
C11	0.0475 (11)	0.0313 (10)	0.0388 (10)	−0.0080 (8)	0.0027 (9)	−0.0031 (8)
C42	0.0447 (11)	0.0316 (10)	0.0386 (10)	−0.0016 (8)	−0.0004 (8)	−0.0018 (8)
C43	0.0427 (11)	0.0378 (10)	0.0364 (10)	−0.0004 (8)	−0.0011 (8)	−0.0071 (8)
C41	0.0426 (10)	0.0331 (10)	0.0430 (11)	−0.0018 (8)	0.0011 (8)	−0.0081 (8)
C9	0.0491 (11)	0.0370 (10)	0.0317 (10)	−0.0030 (8)	−0.0019 (8)	−0.0073 (8)
C1	0.0426 (10)	0.0404 (11)	0.0385 (10)	0.0036 (8)	−0.0083 (8)	−0.0090 (8)
C33	0.0442 (11)	0.0324 (9)	0.0337 (10)	−0.0039 (8)	0.0011 (8)	−0.0049 (8)
C44	0.0427 (10)	0.0322 (10)	0.0446 (11)	−0.0004 (8)	−0.0001 (8)	−0.0107 (8)
C10	0.0528 (11)	0.0403 (11)	0.0383 (10)	−0.0108 (9)	−0.0007 (9)	−0.0070 (8)
C40	0.0401 (10)	0.0346 (10)	0.0387 (10)	−0.0035 (8)	0.0009 (8)	−0.0061 (8)
C39	0.0458 (11)	0.0360 (10)	0.0431 (11)	−0.0052 (8)	0.0004 (9)	−0.0079 (9)
C8	0.0397 (10)	0.0358 (10)	0.0434 (11)	−0.0025 (8)	−0.0039 (8)	−0.0027 (8)
C19	0.0442 (11)	0.0434 (11)	0.0455 (11)	−0.0163 (9)	0.0103 (9)	−0.0082 (9)
C45	0.0462 (11)	0.0338 (10)	0.0423 (11)	−0.0028 (8)	−0.0004 (8)	−0.0029 (8)
C61	0.0525 (12)	0.0298 (10)	0.0494 (12)	0.0009 (8)	−0.0037 (9)	−0.0061 (8)
C34	0.0466 (12)	0.0433 (11)	0.0462 (12)	−0.0068 (9)	0.0023 (9)	−0.0004 (9)
C47	0.0615 (13)	0.0285 (10)	0.0451 (11)	−0.0020 (9)	−0.0040 (10)	−0.0086 (8)
C18	0.0534 (12)	0.0438 (11)	0.0416 (11)	−0.0146 (9)	0.0132 (9)	−0.0044 (9)
C38	0.0462 (11)	0.0440 (11)	0.0406 (11)	−0.0061 (9)	0.0029 (9)	−0.0043 (9)
C7	0.0485 (11)	0.0372 (10)	0.0496 (12)	−0.0055 (9)	−0.0086 (9)	−0.0095 (9)
C6	0.0576 (13)	0.0541 (13)	0.0481 (12)	0.0066 (10)	−0.0134 (10)	−0.0189 (10)
C60	0.0590 (12)	0.0301 (10)	0.0471 (12)	−0.0038 (9)	0.0019 (9)	−0.0036 (8)
C3	0.0573 (12)	0.0578 (14)	0.0453 (12)	−0.0120 (10)	0.0036 (10)	−0.0051 (10)
C5	0.0641 (14)	0.0801 (17)	0.0397 (12)	0.0103 (12)	−0.0001 (11)	−0.0162 (12)
C35	0.0555 (13)	0.0547 (13)	0.0558 (13)	0.0043 (10)	−0.0093 (11)	−0.0010 (11)
C37	0.0637 (14)	0.0485 (12)	0.0411 (11)	−0.0102 (11)	0.0088 (10)	−0.0023 (9)
C46	0.0782 (14)	0.0322 (11)	0.0500 (12)	0.0032 (10)	−0.0033 (10)	−0.0094 (9)
C36	0.0771 (16)	0.0485 (13)	0.0436 (12)	−0.0032 (11)	−0.0044 (11)	0.0060 (10)
C54	0.0406 (11)	0.0558 (13)	0.0399 (11)	0.0013 (9)	−0.0050 (9)	−0.0079 (9)
C26A	0.050 (6)	0.054 (6)	0.055 (6)	−0.019 (4)	−0.027 (5)	−0.002 (4)
C53	0.0533 (12)	0.0540 (13)	0.0484 (12)	0.0059 (10)	−0.0110 (10)	−0.0093 (10)
C24	0.0581 (13)	0.0613 (15)	0.0653 (15)	−0.0213 (11)	0.0024 (11)	−0.0209 (12)
C4	0.0625 (14)	0.0784 (17)	0.0442 (13)	−0.0059 (12)	0.0084 (11)	−0.0059 (12)
C59	0.0624 (13)	0.0551 (14)	0.0496 (12)	−0.0092 (11)	0.0002 (10)	−0.0118 (11)
C20	0.0715 (15)	0.0524 (14)	0.0549 (14)	−0.0148 (11)	0.0076 (11)	−0.0022 (11)
C66	0.0613 (14)	0.0509 (13)	0.0808 (17)	−0.0046 (11)	0.0063 (12)	−0.0240 (12)
C62	0.0574 (13)	0.0490 (13)	0.0758 (16)	−0.0046 (10)	−0.0024 (11)	−0.0211 (12)
C58	0.0718 (15)	0.0589 (15)	0.0639 (15)	−0.0035 (12)	−0.0027 (12)	−0.0181 (12)
C52	0.0658 (14)	0.0609 (15)	0.0550 (14)	−0.0097 (11)	−0.0047 (11)	0.0013 (11)
C25	0.0568 (14)	0.0909 (19)	0.0605 (15)	−0.0380 (13)	−0.0102 (11)	0.0001 (13)
C48	0.0694 (16)	0.0623 (15)	0.0692 (16)	0.0072 (12)	0.0003 (12)	−0.0085 (13)
C65	0.0716 (16)	0.0647 (16)	0.0894 (19)	0.0102 (13)	0.0058 (14)	−0.0348 (14)
C64	0.0864 (18)	0.0556 (15)	0.0918 (19)	0.0132 (13)	−0.0182 (15)	−0.0395 (14)
C63	0.0731 (17)	0.0625 (16)	0.105 (2)	−0.0088 (13)	−0.0119 (15)	−0.0405 (15)
C50	0.129 (2)	0.0510 (15)	0.0602 (17)	0.0119 (16)	−0.0198 (17)	0.0010 (12)
C23	0.0809 (18)	0.0714 (18)	0.093 (2)	−0.0315 (15)	0.0206 (15)	−0.0434 (16)
C51	0.106 (2)	0.0658 (17)	0.0635 (17)	−0.0126 (16)	−0.0011 (15)	0.0060 (13)
C22	0.0860 (19)	0.0518 (16)	0.118 (3)	−0.0198 (14)	0.0371 (18)	−0.0310 (17)
C55	0.0868 (17)	0.0682 (16)	0.0456 (13)	0.0260 (13)	−0.0041 (12)	−0.0040 (12)
C31A	0.074 (7)	0.061 (6)	0.058 (5)	−0.025 (6)	−0.019 (4)	−0.005 (4)
C57	0.0926 (18)	0.084 (2)	0.0584 (16)	0.0189 (15)	−0.0060 (13)	−0.0296 (14)
C21	0.0790 (17)	0.0513 (15)	0.099 (2)	−0.0028 (13)	0.0122 (15)	0.0014 (15)
C49	0.0882 (19)	0.081 (2)	0.085 (2)	0.0323 (15)	−0.0213 (17)	−0.0130 (16)
C56	0.123 (2)	0.085 (2)	0.0440 (14)	0.0311 (17)	−0.0040 (14)	−0.0116 (14)
C30A	0.101 (6)	0.078 (6)	0.046 (4)	−0.023 (4)	−0.029 (4)	0.001 (3)
C27A	0.127 (11)	0.043 (4)	0.074 (6)	−0.021 (7)	−0.021 (6)	−0.003 (4)
C28A	0.159 (11)	0.054 (4)	0.073 (6)	−0.011 (7)	−0.029 (7)	−0.020 (4)
C29A	0.113 (9)	0.064 (5)	0.064 (5)	0.001 (5)	−0.019 (5)	−0.021 (4)
C26B	0.047 (6)	0.042 (5)	0.060 (6)	0.005 (4)	−0.008 (4)	−0.007 (4)
C31B	0.070 (6)	0.087 (10)	0.050 (5)	−0.019 (7)	−0.011 (4)	−0.015 (6)
C27B	0.071 (6)	0.044 (4)	0.081 (7)	−0.008 (4)	−0.031 (5)	−0.007 (4)
C28B	0.128 (9)	0.056 (4)	0.097 (8)	0.003 (6)	−0.042 (6)	−0.040 (5)
C29B	0.123 (11)	0.120 (9)	0.066 (7)	−0.025 (9)	−0.022 (7)	−0.030 (6)
C30B	0.108 (7)	0.133 (13)	0.064 (6)	−0.038 (8)	0.006 (5)	−0.017 (7)

Geometric parameters (Å, º)

O1—C11	1.349 (2)	C35—H35	0.9500
O1—C8	1.467 (2)	C35—C36	1.376 (3)
O5—C16	1.3669 (19)	C37—H37	0.9500
O5—C32	1.4231 (19)	C37—C36	1.378 (3)
O9—C43	1.377 (2)	C46—H46A	0.9900
O9—C53	1.436 (2)	C46—H46B	0.9900
O6—C9	1.445 (2)	C36—H36	0.9500
O6—C39	1.352 (2)	C54—C53	1.504 (3)
O3—C14	1.377 (2)	C54—C59	1.379 (3)
O3—C18	1.441 (2)	C54—C55	1.375 (3)
O8—C42	1.368 (2)	C26A—C25	1.542 (16)
O8—C46	1.436 (2)	C26A—C31A	1.368 (13)
O10—C44	1.368 (2)	C26A—C27A	1.395 (13)
O10—C60	1.435 (2)	C53—H53A	0.9900
O4—C15	1.373 (2)	C53—H53B	0.9900
O4—C25	1.445 (2)	C24—H24	0.9500
O2—C11	1.209 (2)	C24—C23	1.387 (3)
O7—C39	1.211 (2)	C4—H4	0.9500
C12—C17	1.390 (2)	C59—H59	0.9500
C12—C13	1.389 (2)	C59—C58	1.372 (3)
C12—C11	1.481 (3)	C20—H20	0.9500
C16—C15	1.400 (2)	C20—C21	1.389 (3)
C16—C17	1.385 (2)	C66—H66	0.9500
C14—C15	1.393 (2)	C66—C65	1.381 (3)
C14—C13	1.385 (2)	C62—H62	0.9500
C32—H32A	0.9900	C62—C63	1.382 (3)
C32—H32B	0.9900	C58—H58	0.9500
C32—C33	1.506 (2)	C58—C57	1.367 (3)
C2—C1	1.394 (2)	C52—H52	0.9500
C2—C10	1.511 (2)	C52—C51	1.376 (3)
C2—C3	1.392 (2)	C25—H25A	0.9900
C17—H17	0.9500	C25—H25B	0.9900
C13—H13	0.9500	C25—H25C	0.9900
C42—C43	1.390 (2)	C25—H25D	0.9900
C42—C41	1.390 (2)	C25—C26B	1.428 (17)
C43—C44	1.403 (2)	C48—H48	0.9500
C41—H41	0.9500	C48—C49	1.399 (3)
C41—C40	1.386 (2)	C65—H65	0.9500
C9—H9	1.0000	C65—C64	1.375 (3)
C9—C10	1.515 (2)	C64—H64	0.9500
C9—C8	1.508 (2)	C64—C63	1.362 (3)
C1—C7	1.515 (3)	C63—H63	0.9500
C1—C6	1.393 (2)	C50—H50	0.9500
C33—C34	1.379 (2)	C50—C51	1.353 (4)
C33—C38	1.387 (2)	C50—C49	1.367 (4)
C44—C45	1.383 (2)	C23—H23	0.9500
C10—H10A	0.9900	C23—C22	1.362 (4)
C10—H10B	0.9900	C51—H51	0.9500
C40—C39	1.481 (2)	C22—H22	0.9500
C40—C45	1.391 (2)	C22—C21	1.376 (4)
C8—H8	1.0000	C55—H55	0.9500
C8—C7	1.510 (2)	C55—C56	1.389 (3)
C19—C18	1.496 (3)	C31A—H31A	0.9500
C19—C24	1.377 (3)	C31A—C30A	1.398 (13)
C19—C20	1.381 (3)	C57—H57	0.9500
C45—H45	0.9500	C57—C56	1.366 (3)
C61—C60	1.497 (2)	C21—H21	0.9500
C61—C66	1.377 (3)	C49—H49	0.9500
C61—C62	1.372 (3)	C56—H56	0.9500
C34—H34	0.9500	C30A—H30A	0.9500
C34—C35	1.384 (3)	C30A—C29A	1.370 (13)
C47—C46	1.494 (3)	C27A—H27A	0.9500
C47—C52	1.370 (3)	C27A—C28A	1.393 (12)
C47—C48	1.375 (3)	C28A—H28A	0.9500
C18—H18A	0.9900	C28A—C29A	1.374 (13)
C18—H18B	0.9900	C29A—H29A	0.9500
C38—H38	0.9500	C26B—C31B	1.372 (14)
C38—C37	1.381 (2)	C26B—C27B	1.370 (13)
C7—H7A	0.9900	C31B—H31B	0.9500
C7—H7B	0.9900	C31B—C30B	1.389 (14)
C6—H6	0.9500	C27B—H27B	0.9500
C6—C5	1.380 (3)	C27B—C28B	1.369 (13)
C60—H60A	0.9900	C28B—H28B	0.9500
C60—H60B	0.9900	C28B—C29B	1.356 (13)
C3—H3	0.9500	C29B—H29B	0.9500
C3—C4	1.376 (3)	C29B—C30B	1.377 (13)
C5—H5	0.9500	C30B—H30B	0.9500
C5—C4	1.374 (3)
C11—O1—C8	117.58 (13)	C36—C37—H37	120.0
C16—O5—C32	117.65 (13)	O8—C46—C47	108.61 (15)
C43—O9—C53	119.17 (13)	O8—C46—H46A	110.0
C39—O6—C9	117.90 (14)	O8—C46—H46B	110.0
C14—O3—C18	118.52 (14)	C47—C46—H46A	110.0
C42—O8—C46	116.78 (14)	C47—C46—H46B	110.0
C44—O10—C60	117.86 (14)	H46A—C46—H46B	108.3
C15—O4—C25	116.35 (16)	C35—C36—C37	119.59 (19)
C17—C12—C11	116.74 (16)	C35—C36—H36	120.2
C13—C12—C17	120.95 (17)	C37—C36—H36	120.2
C13—C12—C11	122.30 (16)	C59—C54—C53	120.84 (18)
O5—C16—C15	115.94 (16)	C55—C54—C53	120.6 (2)
O5—C16—C17	124.12 (16)	C55—C54—C59	118.6 (2)
C17—C16—C15	119.95 (16)	C31A—C26A—C25	122.5 (11)
O3—C14—C15	114.43 (16)	C31A—C26A—C27A	116.8 (13)
O3—C14—C13	124.85 (16)	C27A—C26A—C25	120.7 (12)
C13—C14—C15	120.69 (16)	O9—C53—C54	107.60 (15)
O4—C15—C16	118.69 (16)	O9—C53—H53A	110.2
O4—C15—C14	121.50 (16)	O9—C53—H53B	110.2
C14—C15—C16	119.54 (16)	C54—C53—H53A	110.2
O5—C32—H32A	109.9	C54—C53—H53B	110.2
O5—C32—H32B	109.9	H53A—C53—H53B	108.5
O5—C32—C33	108.95 (14)	C19—C24—H24	119.7
H32A—C32—H32B	108.3	C19—C24—C23	120.7 (2)
C33—C32—H32A	109.9	C23—C24—H24	119.7
C33—C32—H32B	109.9	C3—C4—H4	120.0
C1—C2—C10	121.43 (16)	C5—C4—C3	120.0 (2)
C3—C2—C1	118.96 (18)	C5—C4—H4	120.0
C3—C2—C10	119.60 (17)	C54—C59—H59	119.4
C12—C17—H17	120.2	C58—C59—C54	121.2 (2)
C16—C17—C12	119.69 (16)	C58—C59—H59	119.4
C16—C17—H17	120.2	C19—C20—H20	119.7
C12—C13—H13	120.4	C19—C20—C21	120.5 (2)
C14—C13—C12	119.13 (17)	C21—C20—H20	119.7
C14—C13—H13	120.4	C61—C66—H66	119.4
O1—C11—C12	112.21 (15)	C61—C66—C65	121.2 (2)
O2—C11—O1	124.09 (17)	C65—C66—H66	119.4
O2—C11—C12	123.69 (17)	C61—C62—H62	119.6
O8—C42—C43	115.48 (16)	C61—C62—C63	120.8 (2)
O8—C42—C41	124.77 (16)	C63—C62—H62	119.6
C43—C42—C41	119.75 (16)	C59—C58—H58	120.1
O9—C43—C42	122.38 (16)	C57—C58—C59	119.7 (2)
O9—C43—C44	117.55 (16)	C57—C58—H58	120.1
C42—C43—C44	119.90 (16)	C47—C52—H52	119.4
C42—C41—H41	120.2	C47—C52—C51	121.2 (2)
C40—C41—C42	119.61 (17)	C51—C52—H52	119.4
C40—C41—H41	120.2	O4—C25—C26A	111.1 (6)
O6—C9—H9	109.6	O4—C25—H25A	109.4
O6—C9—C10	110.23 (14)	O4—C25—H25B	109.4
O6—C9—C8	106.40 (14)	O4—C25—H25C	108.1
C10—C9—H9	109.6	O4—C25—H25D	108.1
C8—C9—H9	109.6	C26A—C25—H25A	109.4
C8—C9—C10	111.49 (15)	C26A—C25—H25B	109.4
C2—C1—C7	121.32 (17)	H25A—C25—H25B	108.0
C6—C1—C2	118.71 (18)	H25C—C25—H25D	107.3
C6—C1—C7	119.95 (18)	C26B—C25—O4	116.6 (7)
C34—C33—C32	122.35 (16)	C26B—C25—H25C	108.1
C34—C33—C38	118.71 (17)	C26B—C25—H25D	108.1
C38—C33—C32	118.88 (16)	C47—C48—H48	119.8
O10—C44—C43	114.18 (16)	C47—C48—C49	120.3 (2)
O10—C44—C45	125.47 (16)	C49—C48—H48	119.8
C45—C44—C43	120.34 (17)	C66—C65—H65	120.0
C2—C10—C9	111.68 (15)	C64—C65—C66	119.9 (2)
C2—C10—H10A	109.3	C64—C65—H65	120.0
C2—C10—H10B	109.3	C65—C64—H64	120.4
C9—C10—H10A	109.3	C63—C64—C65	119.2 (2)
C9—C10—H10B	109.3	C63—C64—H64	120.4
H10A—C10—H10B	107.9	C62—C63—H63	119.6
C41—C40—C39	120.78 (17)	C64—C63—C62	120.7 (2)
C41—C40—C45	121.34 (17)	C64—C63—H63	119.6
C45—C40—C39	117.86 (16)	C51—C50—H50	119.7
O6—C39—C40	111.25 (15)	C51—C50—C49	120.7 (2)
O7—C39—O6	123.21 (17)	C49—C50—H50	119.7
O7—C39—C40	125.54 (17)	C24—C23—H23	119.9
O1—C8—C9	107.65 (14)	C22—C23—C24	120.3 (3)
O1—C8—H8	110.4	C22—C23—H23	119.9
O1—C8—C7	108.16 (14)	C52—C51—H51	120.0
C9—C8—H8	110.4	C50—C51—C52	120.0 (3)
C9—C8—C7	109.86 (15)	C50—C51—H51	120.0
C7—C8—H8	110.4	C23—C22—H22	120.0
C24—C19—C18	120.7 (2)	C23—C22—C21	119.9 (3)
C24—C19—C20	118.7 (2)	C21—C22—H22	120.0
C20—C19—C18	120.56 (19)	C54—C55—H55	119.8
C44—C45—C40	118.89 (17)	C54—C55—C56	120.4 (2)
C44—C45—H45	120.6	C56—C55—H55	119.8
C40—C45—H45	120.6	C26A—C31A—H31A	119.4
C66—C61—C60	120.66 (18)	C26A—C31A—C30A	121.2 (13)
C62—C61—C60	121.23 (18)	C30A—C31A—H31A	119.4
C62—C61—C66	118.10 (19)	C58—C57—H57	119.9
C33—C34—H34	119.7	C56—C57—C58	120.2 (2)
C33—C34—C35	120.52 (18)	C56—C57—H57	119.9
C35—C34—H34	119.7	C20—C21—H21	120.1
C52—C47—C46	121.10 (19)	C22—C21—C20	119.9 (3)
C52—C47—C48	118.6 (2)	C22—C21—H21	120.1
C48—C47—C46	120.24 (19)	C48—C49—H49	120.4
O3—C18—C19	113.55 (15)	C50—C49—C48	119.2 (2)
O3—C18—H18A	108.9	C50—C49—H49	120.4
O3—C18—H18B	108.9	C55—C56—H56	120.0
C19—C18—H18A	108.9	C57—C56—C55	119.9 (2)
C19—C18—H18B	108.9	C57—C56—H56	120.0
H18A—C18—H18B	107.7	C31A—C30A—H30A	119.3
C33—C38—H38	119.6	C29A—C30A—C31A	121.4 (12)
C37—C38—C33	120.76 (18)	C29A—C30A—H30A	119.3
C37—C38—H38	119.6	C26A—C27A—H27A	118.9
C1—C7—H7A	108.6	C28A—C27A—C26A	122.2 (12)
C1—C7—H7B	108.6	C28A—C27A—H27A	118.9
C8—C7—C1	114.63 (15)	C27A—C28A—H28A	120.1
C8—C7—H7A	108.6	C29A—C28A—C27A	119.9 (11)
C8—C7—H7B	108.6	C29A—C28A—H28A	120.1
H7A—C7—H7B	107.6	C30A—C29A—C28A	118.4 (12)
C1—C6—H6	119.2	C30A—C29A—H29A	120.8
C5—C6—C1	121.6 (2)	C28A—C29A—H29A	120.8
C5—C6—H6	119.2	C31B—C26B—C25	123.2 (12)
O10—C60—C61	105.85 (15)	C27B—C26B—C25	116.6 (13)
O10—C60—H60A	110.6	C27B—C26B—C31B	120.1 (14)
O10—C60—H60B	110.6	C26B—C31B—H31B	120.1
C61—C60—H60A	110.6	C26B—C31B—C30B	119.7 (15)
C61—C60—H60B	110.6	C30B—C31B—H31B	120.1
H60A—C60—H60B	108.7	C26B—C27B—H27B	120.2
C2—C3—H3	119.3	C28B—C27B—C26B	119.6 (12)
C4—C3—C2	121.4 (2)	C28B—C27B—H27B	120.2
C4—C3—H3	119.3	C27B—C28B—H28B	119.3
C6—C5—H5	120.3	C29B—C28B—C27B	121.4 (12)
C4—C5—C6	119.3 (2)	C29B—C28B—H28B	119.3
C4—C5—H5	120.3	C28B—C29B—H29B	120.3
C34—C35—H35	119.8	C28B—C29B—C30B	119.5 (12)
C36—C35—C34	120.4 (2)	C30B—C29B—H29B	120.3
C36—C35—H35	119.8	C31B—C30B—H30B	120.2
C38—C37—H37	120.0	C29B—C30B—C31B	119.7 (13)
C36—C37—C38	120.01 (19)	C29B—C30B—H30B	120.2
O1—C8—C7—C1	74.96 (19)	C19—C24—C23—C22	0.8 (3)
O5—C16—C15—O4	−3.0 (2)	C19—C20—C21—C22	0.9 (3)
O5—C16—C15—C14	−177.08 (15)	C45—C40—C39—O6	−171.38 (15)
O5—C16—C17—C12	178.27 (16)	C45—C40—C39—O7	8.0 (3)
O5—C32—C33—C34	17.9 (2)	C61—C66—C65—C64	−0.7 (4)
O5—C32—C33—C38	−164.91 (16)	C61—C62—C63—C64	0.2 (4)
O9—C43—C44—O10	−9.6 (2)	C34—C33—C38—C37	0.1 (3)
O9—C43—C44—C45	170.80 (15)	C34—C35—C36—C37	−0.3 (3)
O6—C9—C10—C2	−168.72 (14)	C47—C52—C51—C50	0.6 (4)
O6—C9—C8—O1	65.60 (17)	C47—C48—C49—C50	0.1 (4)
O6—C9—C8—C7	−176.84 (13)	C18—O3—C14—C15	−179.50 (15)
O3—C14—C15—O4	1.6 (2)	C18—O3—C14—C13	−1.7 (3)
O3—C14—C15—C16	175.52 (15)	C18—C19—C24—C23	−178.53 (18)
O3—C14—C13—C12	−176.80 (15)	C18—C19—C20—C21	177.71 (18)
O8—C42—C43—O9	9.6 (2)	C38—C33—C34—C35	1.4 (3)
O8—C42—C43—C44	−175.38 (15)	C38—C37—C36—C35	1.7 (3)
O8—C42—C41—C40	178.27 (16)	C7—C1—C6—C5	−179.03 (18)
O10—C44—C45—C40	−177.94 (16)	C6—C1—C7—C8	−169.56 (15)
O4—C25—C26B—C31B	0 (2)	C6—C5—C4—C3	0.5 (3)
O4—C25—C26B—C27B	−176.3 (11)	C60—O10—C44—C43	−178.52 (15)
C16—O5—C32—C33	179.58 (14)	C60—O10—C44—C45	1.0 (3)
C14—O3—C18—C19	−75.6 (2)	C60—C61—C66—C65	−178.3 (2)
C15—O4—C25—C26A	−101.2 (7)	C60—C61—C62—C63	178.5 (2)
C15—O4—C25—C26B	−99.7 (8)	C3—C2—C1—C7	178.99 (17)
C15—C16—C17—C12	−1.5 (3)	C3—C2—C1—C6	0.6 (3)
C15—C14—C13—C12	0.9 (3)	C3—C2—C10—C9	−159.78 (17)
C32—O5—C16—C15	175.00 (15)	C46—O8—C42—C43	178.28 (16)
C32—O5—C16—C17	−4.8 (3)	C46—O8—C42—C41	−1.5 (3)
C32—C33—C34—C35	178.54 (18)	C46—C47—C52—C51	−177.3 (2)
C32—C33—C38—C37	−177.22 (17)	C46—C47—C48—C49	176.9 (2)
C2—C1—C7—C8	12.1 (2)	C54—C59—C58—C57	0.0 (3)
C2—C1—C6—C5	−0.6 (3)	C54—C55—C56—C57	−0.6 (4)
C2—C3—C4—C5	−0.5 (3)	C26A—C31A—C30A—C29A	1 (3)
C17—C12—C13—C14	0.3 (3)	C26A—C27A—C28A—C29A	2.6 (19)
C17—C12—C11—O1	157.86 (15)	C53—O9—C43—C42	−66.1 (2)
C17—C12—C11—O2	−21.6 (3)	C53—O9—C43—C44	118.75 (18)
C17—C16—C15—O4	176.84 (16)	C53—C54—C59—C58	177.68 (18)
C17—C16—C15—C14	2.7 (3)	C53—C54—C55—C56	−177.4 (2)
C13—C12—C17—C16	0.0 (3)	C24—C19—C18—O3	−45.5 (2)
C13—C12—C11—O1	−21.4 (2)	C24—C19—C20—C21	0.0 (3)
C13—C12—C11—O2	159.08 (18)	C24—C23—C22—C21	0.1 (4)
C13—C14—C15—O4	−176.39 (16)	C59—C54—C53—O9	52.6 (2)
C13—C14—C15—C16	−2.4 (3)	C59—C54—C55—C56	1.7 (3)
C11—O1—C8—C9	−103.96 (17)	C59—C58—C57—C56	1.1 (4)
C11—O1—C8—C7	137.39 (15)	C20—C19—C18—O3	136.81 (18)
C11—C12—C17—C16	−179.32 (16)	C20—C19—C24—C23	−0.8 (3)
C11—C12—C13—C14	179.57 (16)	C66—C61—C60—O10	75.4 (2)
C42—O8—C46—C47	−171.52 (15)	C66—C61—C62—C63	−0.1 (3)
C42—C43—C44—O10	175.08 (15)	C66—C65—C64—C63	0.8 (4)
C42—C43—C44—C45	−4.5 (3)	C62—C61—C60—O10	−103.2 (2)
C42—C41—C40—C39	177.28 (16)	C62—C61—C66—C65	0.3 (3)
C42—C41—C40—C45	−1.4 (3)	C58—C57—C56—C55	−0.8 (4)
C43—O9—C53—C54	−143.27 (16)	C52—C47—C46—O8	−62.4 (2)
C43—C42—C41—C40	−1.5 (3)	C52—C47—C48—C49	−1.3 (3)
C43—C44—C45—C40	1.6 (3)	C25—O4—C15—C16	122.73 (18)
C41—C42—C43—O9	−170.62 (15)	C25—O4—C15—C14	−63.3 (2)
C41—C42—C43—C44	4.4 (3)	C25—C26A—C31A—C30A	178.7 (14)
C41—C40—C39—O6	9.9 (2)	C25—C26A—C27A—C28A	179.6 (11)
C41—C40—C39—O7	−170.74 (18)	C25—C26B—C31B—C30B	−174.2 (15)
C41—C40—C45—C44	1.4 (3)	C25—C26B—C27B—C28B	174.1 (12)
C9—O6—C39—O7	3.7 (3)	C48—C47—C46—O8	119.4 (2)
C9—O6—C39—C40	−176.96 (14)	C48—C47—C52—C51	1.0 (3)
C9—C8—C7—C1	−42.3 (2)	C65—C64—C63—C62	−0.6 (4)
C1—C2—C10—C9	19.5 (2)	C23—C22—C21—C20	−0.9 (4)
C1—C2—C3—C4	−0.1 (3)	C51—C50—C49—C48	1.6 (4)
C1—C6—C5—C4	0.1 (3)	C55—C54—C53—O9	−128.4 (2)
C33—C34—C35—C36	−1.2 (3)	C55—C54—C59—C58	−1.4 (3)
C33—C38—C37—C36	−1.6 (3)	C31A—C26A—C25—O4	−15.5 (18)
C44—O10—C60—C61	174.56 (14)	C31A—C26A—C27A—C28A	0 (2)
C10—C2—C1—C7	−0.3 (3)	C31A—C30A—C29A—C28A	1 (2)
C10—C2—C1—C6	−178.68 (16)	C49—C50—C51—C52	−1.9 (4)
C10—C2—C3—C4	179.24 (18)	C27A—C26A—C25—O4	164.5 (13)
C10—C9—C8—O1	−54.62 (19)	C27A—C26A—C31A—C30A	−1 (3)
C10—C9—C8—C7	62.94 (19)	C27A—C28A—C29A—C30A	−3.0 (17)
C39—O6—C9—C10	−83.79 (18)	C26B—C31B—C30B—C29B	1 (3)
C39—O6—C9—C8	155.19 (15)	C26B—C27B—C28B—C29B	−1 (2)
C39—C40—C45—C44	−177.35 (16)	C31B—C26B—C27B—C28B	−2 (2)
C8—O1—C11—O2	−4.8 (3)	C27B—C26B—C31B—C30B	2 (3)
C8—O1—C11—C12	175.73 (14)	C27B—C28B—C29B—C30B	4 (2)
C8—C9—C10—C2	−50.8 (2)	C28B—C29B—C30B—C31B	−4 (3)

(2R,3S)-1,2,3,4-Tetrahydronaphthalene-2,3-diyl bis(3,4,5-trimethoxybenzoate) (5)

Crystal data

C30H32O10	F(000) = 1168
Mr = 552.55	Dx = 1.295 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 12.147 (8) Å	Cell parameters from 7542 reflections
b = 20.697 (13) Å	θ = 3.2–27.5°
c = 12.702 (9) Å	µ = 0.10 mm^−1
β = 117.432 (5)°	T = 193 K
V = 2834 (3) Å^3	Prism, colourless
Z = 4	0.17 × 0.05 × 0.03 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	4312 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.051
profile data from ω–scans	θmax = 27.3°, θmin = 3.2°
Absorption correction: empirical (using intensity measurements) DTABSCOR	h = −15→14
Tmin = 0.551, Tmax = 1.000	k = −26→17
19152 measured reflections	l = −16→16
6351 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.070	H-atom parameters constrained
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.2555P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
6351 reflections	Δρmax = 0.21 e Å^−3
367 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O5	−0.53432 (15)	−0.89653 (8)	−0.49170 (14)	0.0498 (4)
O8	−0.06315 (14)	−0.48493 (8)	−0.26403 (14)	0.0483 (4)
O10	−0.42162 (15)	−0.60887 (8)	−0.36939 (16)	0.0547 (5)
O1	−0.41098 (16)	−0.78224 (7)	−0.76634 (15)	0.0518 (5)
O9	−0.27227 (15)	−0.50882 (8)	−0.25270 (15)	0.0568 (5)
O4	−0.73363 (16)	−0.83344 (8)	−0.50406 (14)	0.0513 (4)
O3	−0.83623 (15)	−0.73463 (8)	−0.65386 (15)	0.0541 (5)
O7	−0.06825 (17)	−0.64743 (9)	−0.57726 (17)	0.0644 (5)
O2	−0.50896 (18)	−0.68521 (9)	−0.80440 (17)	0.0685 (6)
O6	−0.21321 (19)	−0.71604 (9)	−0.5854 (2)	0.0833 (7)
C22	−0.1795 (2)	−0.62430 (10)	−0.46752 (19)	0.0379 (5)
C23	−0.1005 (2)	−0.57400 (10)	−0.40323 (19)	0.0384 (5)
H23	−0.026053	−0.566066	−0.408242	0.046*
C16	−0.5764 (2)	−0.84501 (10)	−0.56775 (18)	0.0384 (5)
C17	−0.5181 (2)	−0.82224 (11)	−0.63286 (19)	0.0402 (5)
H17	−0.446908	−0.843725	−0.628220	0.048*
C24	−0.1328 (2)	−0.53562 (10)	−0.33160 (19)	0.0374 (5)
C15	−0.6818 (2)	−0.81383 (11)	−0.57535 (19)	0.0396 (5)
C25	−0.2437 (2)	−0.54738 (11)	−0.32526 (19)	0.0405 (5)
C13	−0.6713 (2)	−0.73703 (11)	−0.71495 (19)	0.0412 (5)
H13	−0.702920	−0.700265	−0.764722	0.049*
C26	−0.3191 (2)	−0.59943 (11)	−0.3867 (2)	0.0402 (5)
C27	−0.2876 (2)	−0.63796 (11)	−0.4585 (2)	0.0411 (5)
H27	−0.338999	−0.673186	−0.501047	0.049*
C14	−0.7311 (2)	−0.76071 (11)	−0.65120 (19)	0.0402 (5)
C12	−0.5645 (2)	−0.76811 (11)	−0.70446 (19)	0.0388 (5)
C21	−0.1462 (2)	−0.66230 (11)	−0.5480 (2)	0.0433 (6)
C11	−0.4949 (2)	−0.73958 (12)	−0.7646 (2)	0.0476 (6)
C4	−0.1772 (2)	−0.87960 (13)	−0.6923 (2)	0.0491 (6)
C5	−0.2385 (2)	−0.87002 (12)	−0.8152 (2)	0.0470 (6)
C10	−0.2476 (2)	−0.92254 (13)	−0.8885 (2)	0.0567 (7)
H10	−0.289511	−0.916916	−0.972157	0.068*
C28	0.0576 (2)	−0.47537 (12)	−0.2572 (2)	0.0550 (7)
H28A	0.102045	−0.441634	−0.198753	0.083*
H28B	0.048105	−0.462181	−0.335020	0.083*
H28C	0.104755	−0.515805	−0.233077	0.083*
C20	−0.4212 (2)	−0.92665 (13)	−0.4772 (2)	0.0581 (7)
H20A	−0.396467	−0.960181	−0.416071	0.087*
H20B	−0.355552	−0.894039	−0.453290	0.087*
H20C	−0.434660	−0.946199	−0.552497	0.087*
C7	−0.1286 (2)	−0.94004 (14)	−0.6470 (3)	0.0588 (7)
H7	−0.088559	−0.946604	−0.563626	0.071*
C8	−0.1376 (2)	−0.99089 (14)	−0.7216 (3)	0.0643 (8)
H8	−0.102523	−1.031730	−0.689360	0.077*
C9	−0.1977 (2)	−0.98186 (14)	−0.8430 (3)	0.0631 (8)
H9	−0.204577	−1.016519	−0.894666	0.076*
C30	−0.4959 (2)	−0.66451 (13)	−0.4226 (3)	0.0629 (8)
H30A	−0.443400	−0.703145	−0.399175	0.094*
H30B	−0.535756	−0.660060	−0.509144	0.094*
H30C	−0.559692	−0.668526	−0.396115	0.094*
C1	−0.3080 (3)	−0.75842 (13)	−0.7855 (3)	0.0577 (7)
H1	−0.325391	−0.713680	−0.818984	0.069*
C6	−0.2902 (3)	−0.80482 (12)	−0.8701 (2)	0.0570 (7)
H6A	−0.371033	−0.811385	−0.941016	0.068*
H6B	−0.233138	−0.784768	−0.896544	0.068*
C3	−0.1657 (3)	−0.82511 (14)	−0.6070 (2)	0.0629 (8)
H3A	−0.224050	−0.833192	−0.574052	0.075*
H3B	−0.080588	−0.825177	−0.540246	0.075*
C2	−0.1925 (3)	−0.75932 (13)	−0.6656 (3)	0.0660 (9)
H2	−0.119290	−0.744180	−0.674891	0.079*
C18	−0.8870 (3)	−0.67763 (13)	−0.7239 (3)	0.0692 (8)
H18A	−0.825022	−0.643004	−0.695129	0.104*
H18B	−0.960837	−0.663973	−0.717325	0.104*
H18C	−0.909800	−0.686979	−0.807053	0.104*
C29	−0.3786 (3)	−0.46806 (14)	−0.3129 (3)	0.0776 (9)
H29A	−0.386657	−0.439387	−0.255441	0.116*
H29B	−0.453246	−0.494839	−0.351972	0.116*
H29C	−0.368699	−0.442105	−0.372516	0.116*
C19	−0.8253 (3)	−0.88248 (16)	−0.5537 (3)	0.0780 (9)
H19A	−0.856009	−0.894023	−0.497085	0.117*
H19B	−0.788930	−0.920687	−0.571186	0.117*
H19C	−0.894300	−0.866544	−0.627148	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5	0.0516 (11)	0.0511 (10)	0.0497 (10)	0.0080 (8)	0.0260 (9)	0.0139 (8)
O8	0.0411 (10)	0.0479 (10)	0.0571 (10)	−0.0099 (8)	0.0237 (8)	−0.0141 (8)
O10	0.0474 (10)	0.0616 (11)	0.0693 (12)	−0.0163 (9)	0.0389 (9)	−0.0233 (9)
O1	0.0590 (11)	0.0459 (10)	0.0706 (12)	−0.0029 (8)	0.0471 (10)	−0.0026 (8)
O9	0.0470 (10)	0.0673 (12)	0.0604 (11)	−0.0069 (9)	0.0285 (9)	−0.0274 (9)
O4	0.0590 (11)	0.0565 (10)	0.0524 (10)	−0.0045 (9)	0.0374 (9)	0.0016 (8)
O3	0.0540 (11)	0.0570 (11)	0.0665 (11)	0.0150 (9)	0.0407 (9)	0.0110 (9)
O7	0.0791 (13)	0.0632 (12)	0.0802 (13)	−0.0211 (10)	0.0617 (12)	−0.0205 (10)
O2	0.0878 (14)	0.0580 (12)	0.0852 (14)	0.0154 (10)	0.0615 (12)	0.0255 (10)
O6	0.0903 (15)	0.0761 (14)	0.1291 (18)	−0.0410 (12)	0.0894 (15)	−0.0602 (13)
C22	0.0415 (13)	0.0361 (12)	0.0413 (12)	0.0005 (10)	0.0236 (11)	0.0022 (10)
C23	0.0393 (13)	0.0371 (12)	0.0424 (12)	0.0002 (10)	0.0217 (11)	0.0032 (10)
C16	0.0411 (14)	0.0373 (13)	0.0352 (12)	−0.0005 (10)	0.0162 (11)	0.0006 (10)
C17	0.0391 (13)	0.0423 (13)	0.0421 (12)	0.0006 (10)	0.0212 (11)	−0.0025 (10)
C24	0.0361 (13)	0.0326 (12)	0.0411 (12)	−0.0030 (10)	0.0157 (11)	−0.0008 (10)
C15	0.0416 (13)	0.0436 (13)	0.0390 (12)	−0.0024 (11)	0.0234 (11)	−0.0035 (10)
C25	0.0398 (14)	0.0440 (13)	0.0407 (13)	−0.0011 (11)	0.0210 (11)	−0.0056 (10)
C13	0.0454 (14)	0.0403 (13)	0.0391 (12)	0.0031 (11)	0.0205 (11)	0.0007 (10)
C26	0.0376 (13)	0.0435 (13)	0.0450 (13)	−0.0034 (11)	0.0237 (11)	−0.0041 (10)
C27	0.0447 (14)	0.0364 (13)	0.0452 (13)	−0.0037 (10)	0.0234 (11)	−0.0042 (10)
C14	0.0365 (13)	0.0464 (14)	0.0405 (12)	0.0042 (11)	0.0202 (11)	−0.0028 (10)
C12	0.0439 (14)	0.0400 (13)	0.0374 (12)	−0.0008 (11)	0.0228 (11)	−0.0021 (10)
C21	0.0452 (15)	0.0393 (13)	0.0510 (14)	−0.0053 (11)	0.0269 (12)	−0.0052 (11)
C11	0.0551 (16)	0.0463 (15)	0.0490 (14)	0.0034 (12)	0.0306 (13)	0.0007 (12)
C4	0.0393 (14)	0.0587 (16)	0.0568 (16)	−0.0083 (12)	0.0285 (13)	−0.0145 (13)
C5	0.0463 (15)	0.0505 (15)	0.0572 (15)	−0.0076 (12)	0.0350 (13)	−0.0101 (12)
C10	0.0552 (17)	0.0624 (18)	0.0605 (16)	−0.0093 (14)	0.0334 (14)	−0.0160 (14)
C28	0.0447 (15)	0.0566 (16)	0.0666 (17)	−0.0118 (13)	0.0280 (14)	−0.0066 (13)
C20	0.0627 (18)	0.0611 (17)	0.0515 (15)	0.0202 (14)	0.0271 (14)	0.0159 (13)
C7	0.0410 (15)	0.0716 (19)	0.0601 (17)	−0.0023 (14)	0.0201 (13)	−0.0028 (15)
C8	0.0474 (17)	0.0512 (17)	0.093 (2)	−0.0038 (13)	0.0315 (17)	−0.0095 (16)
C9	0.0548 (18)	0.0569 (18)	0.080 (2)	−0.0121 (14)	0.0325 (16)	−0.0270 (16)
C30	0.0530 (17)	0.0626 (17)	0.086 (2)	−0.0219 (14)	0.0427 (16)	−0.0251 (15)
C1	0.0685 (19)	0.0484 (15)	0.085 (2)	−0.0070 (13)	0.0602 (18)	−0.0029 (14)
C6	0.0695 (18)	0.0587 (17)	0.0658 (17)	−0.0028 (14)	0.0510 (15)	−0.0039 (13)
C3	0.0519 (17)	0.078 (2)	0.0617 (17)	−0.0055 (15)	0.0290 (14)	−0.0260 (15)
C2	0.0673 (19)	0.0643 (19)	0.096 (2)	−0.0241 (15)	0.0630 (19)	−0.0419 (17)
C18	0.0700 (19)	0.0572 (17)	0.098 (2)	0.0265 (15)	0.0542 (18)	0.0216 (16)
C29	0.068 (2)	0.0632 (19)	0.111 (3)	0.0052 (16)	0.0490 (19)	−0.0254 (18)
C19	0.068 (2)	0.099 (2)	0.075 (2)	−0.0301 (18)	0.0408 (17)	−0.0019 (18)

Geometric parameters (Å, º)

O5—C16	1.370 (3)	C4—C3	1.524 (3)
O5—C20	1.442 (3)	C5—C10	1.403 (3)
O8—C24	1.373 (3)	C5—C6	1.516 (4)
O8—C28	1.443 (3)	C10—H10	0.9500
O10—C26	1.375 (3)	C10—C9	1.374 (4)
O10—C30	1.427 (3)	C28—H28A	0.9800
O1—C11	1.356 (3)	C28—H28B	0.9800
O1—C1	1.465 (3)	C28—H28C	0.9800
O9—C25	1.379 (3)	C20—H20A	0.9800
O9—C29	1.434 (3)	C20—H20B	0.9800
O4—C15	1.381 (3)	C20—H20C	0.9800
O4—C19	1.422 (3)	C7—H7	0.9500
O3—C14	1.372 (3)	C7—C8	1.386 (4)
O3—C18	1.434 (3)	C8—H8	0.9500
O7—C21	1.205 (3)	C8—C9	1.381 (4)
O2—C11	1.213 (3)	C9—H9	0.9500
O6—C21	1.330 (3)	C30—H30A	0.9800
O6—C2	1.463 (3)	C30—H30B	0.9800
C22—C23	1.396 (3)	C30—H30C	0.9800
C22—C27	1.399 (3)	C1—H1	1.0000
C22—C21	1.486 (3)	C1—C6	1.529 (3)
C23—H23	0.9500	C1—C2	1.523 (4)
C23—C24	1.393 (3)	C6—H6A	0.9900
C16—C17	1.395 (3)	C6—H6B	0.9900
C16—C15	1.397 (3)	C3—H3A	0.9900
C17—H17	0.9500	C3—H3B	0.9900
C17—C12	1.388 (3)	C3—C2	1.513 (4)
C24—C25	1.407 (3)	C2—H2	1.0000
C15—C14	1.402 (3)	C18—H18A	0.9800
C25—C26	1.397 (3)	C18—H18B	0.9800
C13—H13	0.9500	C18—H18C	0.9800
C13—C14	1.403 (3)	C29—H29A	0.9800
C13—C12	1.398 (3)	C29—H29B	0.9800
C26—C27	1.391 (3)	C29—H29C	0.9800
C27—H27	0.9500	C19—H19A	0.9800
C12—C11	1.498 (3)	C19—H19B	0.9800
C4—C5	1.400 (4)	C19—H19C	0.9800
C4—C7	1.390 (4)
C16—O5—C20	116.76 (18)	H28B—C28—H28C	109.5
C24—O8—C28	117.33 (18)	O5—C20—H20A	109.5
C26—O10—C30	117.43 (18)	O5—C20—H20B	109.5
C11—O1—C1	119.26 (19)	O5—C20—H20C	109.5
C25—O9—C29	115.2 (2)	H20A—C20—H20B	109.5
C15—O4—C19	114.81 (19)	H20A—C20—H20C	109.5
C14—O3—C18	117.91 (18)	H20B—C20—H20C	109.5
C21—O6—C2	119.15 (19)	C4—C7—H7	119.5
C23—C22—C27	121.4 (2)	C8—C7—C4	121.1 (3)
C23—C22—C21	117.8 (2)	C8—C7—H7	119.5
C27—C22—C21	120.8 (2)	C7—C8—H8	120.2
C22—C23—H23	120.6	C9—C8—C7	119.6 (3)
C24—C23—C22	118.9 (2)	C9—C8—H8	120.2
C24—C23—H23	120.6	C10—C9—C8	119.7 (3)
O5—C16—C17	123.7 (2)	C10—C9—H9	120.2
O5—C16—C15	116.13 (19)	C8—C9—H9	120.2
C17—C16—C15	120.1 (2)	O10—C30—H30A	109.5
C16—C17—H17	120.1	O10—C30—H30B	109.5
C12—C17—C16	119.9 (2)	O10—C30—H30C	109.5
C12—C17—H17	120.1	H30A—C30—H30B	109.5
O8—C24—C23	124.5 (2)	H30A—C30—H30C	109.5
O8—C24—C25	115.27 (19)	H30B—C30—H30C	109.5
C23—C24—C25	120.2 (2)	O1—C1—H1	110.7
O4—C15—C16	120.0 (2)	O1—C1—C6	108.3 (2)
O4—C15—C14	120.1 (2)	O1—C1—C2	107.1 (2)
C16—C15—C14	119.9 (2)	C6—C1—H1	110.7
O9—C25—C24	118.7 (2)	C2—C1—H1	110.7
O9—C25—C26	121.2 (2)	C2—C1—C6	109.3 (2)
C26—C25—C24	120.0 (2)	C5—C6—C1	113.5 (2)
C14—C13—H13	120.4	C5—C6—H6A	108.9
C12—C13—H13	120.4	C5—C6—H6B	108.9
C12—C13—C14	119.3 (2)	C1—C6—H6A	108.9
O10—C26—C25	115.40 (19)	C1—C6—H6B	108.9
O10—C26—C27	124.5 (2)	H6A—C6—H6B	107.7
C27—C26—C25	120.1 (2)	C4—C3—H3A	109.0
C22—C27—H27	120.3	C4—C3—H3B	109.0
C26—C27—C22	119.3 (2)	H3A—C3—H3B	107.8
C26—C27—H27	120.3	C2—C3—C4	112.8 (2)
O3—C14—C15	115.10 (19)	C2—C3—H3A	109.0
O3—C14—C13	124.9 (2)	C2—C3—H3B	109.0
C15—C14—C13	120.0 (2)	O6—C2—C1	108.3 (2)
C17—C12—C13	120.8 (2)	O6—C2—C3	106.0 (2)
C17—C12—C11	119.9 (2)	O6—C2—H2	109.8
C13—C12—C11	119.1 (2)	C1—C2—H2	109.8
O7—C21—O6	122.8 (2)	C3—C2—C1	113.2 (2)
O7—C21—C22	125.3 (2)	C3—C2—H2	109.8
O6—C21—C22	111.84 (19)	O3—C18—H18A	109.5
O1—C11—C12	110.9 (2)	O3—C18—H18B	109.5
O2—C11—O1	124.1 (2)	O3—C18—H18C	109.5
O2—C11—C12	125.0 (2)	H18A—C18—H18B	109.5
C5—C4—C3	121.0 (2)	H18A—C18—H18C	109.5
C7—C4—C5	119.7 (2)	H18B—C18—H18C	109.5
C7—C4—C3	119.3 (2)	O9—C29—H29A	109.5
C4—C5—C10	118.0 (2)	O9—C29—H29B	109.5
C4—C5—C6	122.3 (2)	O9—C29—H29C	109.5
C10—C5—C6	119.7 (2)	H29A—C29—H29B	109.5
C5—C10—H10	119.1	H29A—C29—H29C	109.5
C9—C10—C5	121.9 (3)	H29B—C29—H29C	109.5
C9—C10—H10	119.1	O4—C19—H19A	109.5
O8—C28—H28A	109.5	O4—C19—H19B	109.5
O8—C28—H28B	109.5	O4—C19—H19C	109.5
O8—C28—H28C	109.5	H19A—C19—H19B	109.5
H28A—C28—H28B	109.5	H19A—C19—H19C	109.5
H28A—C28—H28C	109.5	H19B—C19—H19C	109.5
O5—C16—C17—C12	−177.5 (2)	C21—O6—C2—C3	125.3 (3)
O5—C16—C15—O4	3.2 (3)	C21—C22—C23—C24	176.9 (2)
O5—C16—C15—C14	−179.90 (19)	C21—C22—C27—C26	−176.9 (2)
O8—C24—C25—O9	−0.8 (3)	C11—O1—C1—C6	−138.2 (2)
O8—C24—C25—C26	−177.4 (2)	C11—O1—C1—C2	104.0 (2)
O10—C26—C27—C22	−178.8 (2)	C4—C5—C10—C9	−0.5 (4)
O1—C1—C6—C5	−70.1 (3)	C4—C5—C6—C1	−19.2 (3)
O1—C1—C2—O6	−61.3 (3)	C4—C7—C8—C9	−1.2 (4)
O1—C1—C2—C3	55.9 (3)	C4—C3—C2—O6	164.0 (2)
O9—C25—C26—O10	0.0 (3)	C4—C3—C2—C1	45.4 (3)
O9—C25—C26—C27	−179.4 (2)	C5—C4—C7—C8	1.3 (4)
O4—C15—C14—O3	−4.5 (3)	C5—C4—C3—C2	−16.2 (3)
O4—C15—C14—C13	173.9 (2)	C5—C10—C9—C8	0.6 (4)
C22—C23—C24—O8	179.86 (19)	C10—C5—C6—C1	163.2 (2)
C22—C23—C24—C25	−0.4 (3)	C28—O8—C24—C23	−7.0 (3)
C23—C22—C27—C26	1.9 (3)	C28—O8—C24—C25	173.3 (2)
C23—C22—C21—O7	−12.5 (4)	C20—O5—C16—C17	2.0 (3)
C23—C22—C21—O6	167.4 (2)	C20—O5—C16—C15	−176.2 (2)
C23—C24—C25—O9	179.5 (2)	C7—C4—C5—C10	−0.4 (3)
C23—C24—C25—C26	2.9 (3)	C7—C4—C5—C6	−178.1 (2)
C16—C17—C12—C13	−1.9 (3)	C7—C4—C3—C2	165.3 (2)
C16—C17—C12—C11	173.8 (2)	C7—C8—C9—C10	0.3 (4)
C16—C15—C14—O3	178.59 (19)	C30—O10—C26—C25	−175.0 (2)
C16—C15—C14—C13	−3.1 (3)	C30—O10—C26—C27	4.3 (3)
C17—C16—C15—O4	−175.08 (19)	C1—O1—C11—O2	17.9 (4)
C17—C16—C15—C14	1.9 (3)	C1—O1—C11—C12	−160.6 (2)
C17—C12—C11—O1	17.2 (3)	C6—C5—C10—C9	177.2 (2)
C17—C12—C11—O2	−161.3 (2)	C6—C1—C2—O6	−178.4 (2)
C24—C25—C26—O10	176.5 (2)	C6—C1—C2—C3	−61.2 (3)
C24—C25—C26—C27	−2.9 (3)	C3—C4—C5—C10	−178.9 (2)
C15—C16—C17—C12	0.6 (3)	C3—C4—C5—C6	3.4 (3)
C25—C26—C27—C22	0.5 (3)	C3—C4—C7—C8	179.8 (2)
C13—C12—C11—O1	−167.11 (19)	C2—O6—C21—O7	−0.1 (4)
C13—C12—C11—O2	14.4 (4)	C2—O6—C21—C22	180.0 (2)
C27—C22—C23—C24	−2.0 (3)	C2—C1—C6—C5	46.3 (3)
C27—C22—C21—O7	166.3 (2)	C18—O3—C14—C15	176.1 (2)
C27—C22—C21—O6	−13.7 (3)	C18—O3—C14—C13	−2.1 (3)
C14—C13—C12—C17	0.6 (3)	C29—O9—C25—C24	113.3 (2)
C14—C13—C12—C11	−175.0 (2)	C29—O9—C25—C26	−70.1 (3)
C12—C13—C14—O3	180.0 (2)	C19—O4—C15—C16	−89.8 (3)
C12—C13—C14—C15	1.8 (3)	C19—O4—C15—C14	93.3 (3)
C21—O6—C2—C1	−113.0 (3)

(2R,3S)-1,2,3,4-Tetrahydronaphthalene-2,3-diyl bis(3,4,5-trifluorobenzoate) (6)

Crystal data

C24H14F6O4	F(000) = 1952
Mr = 480.35	Dx = 1.538 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
a = 30.399 (10) Å	Cell parameters from 4720 reflections
b = 9.176 (3) Å	θ = 3.0–27.5°
c = 14.994 (5) Å	µ = 0.14 mm^−1
β = 97.204 (4)°	T = 193 K
V = 4150 (2) Å^3	Prism, colourless
Z = 8	0.18 × 0.09 × 0.09 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	3317 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.036
dtprofit.ref scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) DTABSCOR	h = −39→39
Tmin = 0.713, Tmax = 1.000	k = −11→11
20773 measured reflections	l = −19→19
4718 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0689P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
4718 reflections	Δρmax = 0.20 e Å^−3
307 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	−0.42150 (3)	−0.24401 (9)	−0.29860 (6)	0.0457 (2)
F5	−0.29014 (3)	−0.26696 (10)	−0.75797 (6)	0.0727 (3)
O3	−0.34776 (3)	−0.14683 (10)	−0.37857 (6)	0.0513 (2)
O4	−0.28229 (3)	−0.02898 (12)	−0.36197 (7)	0.0600 (3)
F4	−0.23441 (3)	−0.07078 (12)	−0.67027 (6)	0.0818 (3)
F6	−0.35691 (3)	−0.37908 (12)	−0.67886 (6)	0.0882 (3)
O2	−0.48416 (3)	−0.14070 (12)	−0.36481 (9)	0.0796 (4)
F1	−0.57826 (4)	−0.57051 (14)	−0.46755 (7)	0.1059 (4)
F3	−0.45007 (4)	−0.77437 (11)	−0.31262 (8)	0.1056 (4)
F2	−0.53110 (5)	−0.80613 (12)	−0.40746 (8)	0.1213 (5)
C19	−0.30713 (4)	−0.14181 (14)	−0.50193 (9)	0.0455 (3)
C18	−0.31038 (4)	−0.09802 (15)	−0.40761 (9)	0.0476 (3)
C12	−0.47953 (4)	−0.39868 (14)	−0.35625 (8)	0.0438 (3)
C24	−0.33582 (5)	−0.24260 (15)	−0.54698 (10)	0.0546 (4)
H24	−0.359297	−0.283633	−0.518978	0.066*
C5	−0.38171 (4)	−0.14037 (15)	−0.11268 (9)	0.0521 (3)
C11	−0.46275 (4)	−0.24714 (14)	−0.34107 (9)	0.0460 (3)
C3	−0.33177 (4)	−0.23110 (17)	−0.22433 (9)	0.0559 (4)
H3A	−0.340438	−0.327858	−0.249968	0.067*
H3B	−0.299146	−0.222529	−0.221040	0.067*
C20	−0.27298 (4)	−0.08240 (15)	−0.54366 (9)	0.0502 (3)
H20	−0.253370	−0.013052	−0.513025	0.060*
C2	−0.35328 (4)	−0.11385 (15)	−0.28586 (9)	0.0499 (3)
H2	−0.338585	−0.018539	−0.268980	0.060*
C4	−0.34486 (4)	−0.22103 (16)	−0.13056 (9)	0.0535 (4)
C6	−0.40911 (4)	−0.05403 (15)	−0.18551 (10)	0.0533 (4)
H6A	−0.401557	0.050513	−0.177655	0.064*
H6B	−0.440867	−0.065419	−0.178400	0.064*
C23	−0.32960 (5)	−0.28181 (16)	−0.63285 (10)	0.0565 (4)
C13	−0.52183 (4)	−0.41464 (17)	−0.40317 (8)	0.0540 (4)
H13	−0.538970	−0.331635	−0.423176	0.065*
C22	−0.29575 (5)	−0.22500 (15)	−0.67471 (9)	0.0536 (4)
C1	−0.40215 (4)	−0.09992 (14)	−0.27959 (9)	0.0475 (3)
H1	−0.415907	−0.027404	−0.324470	0.057*
C17	−0.45477 (5)	−0.51907 (15)	−0.32590 (9)	0.0517 (3)
H17	−0.425934	−0.508165	−0.293956	0.062*
C10	−0.39252 (5)	−0.13788 (18)	−0.02492 (10)	0.0638 (4)
H10	−0.417454	−0.083226	−0.011767	0.077*
C21	−0.26781 (4)	−0.12459 (16)	−0.62926 (10)	0.0537 (4)
C14	−0.53810 (6)	−0.5516 (2)	−0.41978 (10)	0.0688 (5)
C7	−0.32021 (6)	−0.29590 (19)	−0.06109 (11)	0.0697 (5)
H7	−0.295142	−0.350722	−0.073316	0.084*
C9	−0.36760 (7)	−0.21340 (19)	0.04277 (11)	0.0756 (5)
H9	−0.375514	−0.210948	0.102072	0.091*
C16	−0.47285 (7)	−0.65502 (16)	−0.34303 (11)	0.0683 (5)
C15	−0.51432 (7)	−0.67264 (19)	−0.38997 (11)	0.0757 (5)
C8	−0.33119 (7)	−0.2927 (2)	0.02488 (12)	0.0794 (5)
H8	−0.313866	−0.344500	0.071637	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0407 (5)	0.0372 (5)	0.0559 (6)	−0.0003 (4)	−0.0066 (4)	−0.0027 (4)
F5	0.0893 (7)	0.0764 (6)	0.0500 (5)	0.0105 (5)	−0.0009 (5)	−0.0039 (4)
O3	0.0445 (5)	0.0564 (6)	0.0513 (6)	−0.0098 (4)	−0.0004 (4)	−0.0067 (4)
O4	0.0462 (5)	0.0686 (7)	0.0623 (6)	−0.0125 (5)	−0.0049 (5)	−0.0123 (5)
F4	0.0796 (7)	0.0959 (8)	0.0730 (6)	−0.0177 (5)	0.0225 (5)	−0.0008 (5)
F6	0.0932 (7)	0.0945 (7)	0.0731 (6)	−0.0333 (6)	−0.0051 (5)	−0.0287 (5)
O2	0.0558 (6)	0.0465 (6)	0.1262 (10)	0.0073 (5)	−0.0282 (6)	0.0005 (6)
F1	0.0866 (7)	0.1446 (11)	0.0837 (7)	−0.0705 (7)	0.0002 (6)	−0.0150 (7)
F3	0.1548 (11)	0.0424 (5)	0.1244 (9)	0.0034 (6)	0.0357 (8)	0.0136 (5)
F2	0.1773 (13)	0.0744 (7)	0.1191 (9)	−0.0741 (8)	0.0461 (9)	−0.0233 (7)
C19	0.0397 (7)	0.0421 (7)	0.0515 (8)	0.0035 (5)	−0.0071 (6)	−0.0004 (6)
C18	0.0401 (7)	0.0451 (7)	0.0554 (8)	−0.0008 (6)	−0.0032 (6)	−0.0013 (6)
C12	0.0486 (7)	0.0455 (7)	0.0376 (7)	−0.0068 (6)	0.0061 (5)	−0.0029 (5)
C24	0.0461 (7)	0.0548 (8)	0.0603 (9)	−0.0070 (6)	−0.0037 (6)	−0.0028 (7)
C5	0.0498 (8)	0.0492 (8)	0.0555 (9)	−0.0047 (6)	−0.0009 (6)	−0.0140 (6)
C11	0.0402 (7)	0.0434 (7)	0.0523 (8)	0.0018 (5)	−0.0032 (6)	−0.0030 (6)
C3	0.0420 (7)	0.0673 (9)	0.0562 (9)	0.0075 (7)	−0.0023 (6)	−0.0063 (7)
C20	0.0445 (7)	0.0466 (7)	0.0570 (9)	−0.0009 (6)	−0.0033 (6)	−0.0002 (6)
C2	0.0440 (7)	0.0523 (8)	0.0516 (8)	−0.0062 (6)	−0.0007 (6)	−0.0094 (6)
C4	0.0484 (8)	0.0575 (8)	0.0518 (8)	−0.0001 (6)	−0.0046 (6)	−0.0109 (6)
C6	0.0466 (7)	0.0445 (7)	0.0676 (9)	0.0002 (6)	0.0023 (7)	−0.0133 (6)
C23	0.0563 (8)	0.0531 (8)	0.0555 (9)	−0.0034 (7)	−0.0112 (7)	−0.0082 (7)
C13	0.0519 (8)	0.0656 (9)	0.0439 (8)	−0.0145 (7)	0.0035 (6)	−0.0015 (7)
C22	0.0594 (9)	0.0528 (8)	0.0454 (8)	0.0132 (7)	−0.0058 (7)	0.0005 (6)
C1	0.0438 (7)	0.0374 (7)	0.0590 (8)	−0.0022 (5)	−0.0026 (6)	−0.0042 (6)
C17	0.0637 (8)	0.0431 (7)	0.0495 (8)	−0.0026 (6)	0.0125 (7)	−0.0002 (6)
C10	0.0657 (9)	0.0652 (10)	0.0605 (10)	−0.0042 (8)	0.0080 (8)	−0.0210 (8)
C21	0.0489 (8)	0.0537 (8)	0.0571 (9)	0.0036 (6)	0.0018 (7)	0.0068 (7)
C14	0.0702 (10)	0.0876 (13)	0.0498 (9)	−0.0411 (9)	0.0118 (8)	−0.0093 (8)
C7	0.0685 (10)	0.0790 (11)	0.0573 (10)	0.0162 (9)	−0.0086 (8)	−0.0089 (8)
C9	0.0986 (13)	0.0769 (12)	0.0509 (9)	−0.0070 (10)	0.0073 (9)	−0.0149 (8)
C16	0.1036 (13)	0.0409 (8)	0.0650 (10)	−0.0060 (8)	0.0293 (9)	0.0038 (7)
C15	0.1103 (15)	0.0588 (10)	0.0632 (10)	−0.0438 (10)	0.0307 (10)	−0.0132 (8)
C8	0.0974 (13)	0.0846 (12)	0.0519 (10)	0.0137 (11)	−0.0077 (9)	−0.0064 (9)

Geometric parameters (Å, º)

O1—C11	1.3336 (16)	C3—C4	1.511 (2)
O1—C1	1.4606 (15)	C20—H20	0.9500
F5—C22	1.3376 (16)	C20—C21	1.368 (2)
O3—C18	1.3437 (16)	C2—H2	1.0000
O3—C2	1.4529 (16)	C2—C1	1.5060 (18)
O4—C18	1.2050 (15)	C4—C7	1.387 (2)
F4—C21	1.3451 (17)	C6—H6A	0.9900
F6—C23	1.3484 (16)	C6—H6B	0.9900
O2—C11	1.2026 (16)	C6—C1	1.512 (2)
F1—C14	1.3468 (19)	C23—C22	1.373 (2)
F3—C16	1.3445 (19)	C13—H13	0.9500
F2—C15	1.3401 (18)	C13—C14	1.362 (2)
C19—C18	1.4855 (19)	C22—C21	1.375 (2)
C19—C24	1.3874 (18)	C1—H1	1.0000
C19—C20	1.3890 (19)	C17—H17	0.9500
C12—C11	1.4888 (18)	C17—C16	1.374 (2)
C12—C13	1.3940 (17)	C10—H10	0.9500
C12—C17	1.3813 (19)	C10—C9	1.375 (2)
C24—H24	0.9500	C14—C15	1.369 (3)
C24—C23	1.373 (2)	C7—H7	0.9500
C5—C4	1.3963 (19)	C7—C8	1.372 (2)
C5—C6	1.512 (2)	C9—H9	0.9500
C5—C10	1.396 (2)	C9—C8	1.379 (3)
C3—H3A	0.9900	C16—C15	1.374 (3)
C3—H3B	0.9900	C8—H8	0.9500
C3—C2	1.512 (2)
C11—O1—C1	116.37 (10)	C1—C6—H6B	108.9
C18—O3—C2	116.38 (9)	F6—C23—C24	120.33 (13)
C24—C19—C18	122.08 (13)	F6—C23—C22	117.77 (13)
C24—C19—C20	120.14 (13)	C24—C23—C22	121.90 (13)
C20—C19—C18	117.74 (12)	C12—C13—H13	120.7
O3—C18—C19	112.23 (11)	C14—C13—C12	118.69 (15)
O4—C18—O3	123.99 (12)	C14—C13—H13	120.7
O4—C18—C19	123.77 (12)	F5—C22—C23	120.51 (13)
C13—C12—C11	116.87 (12)	F5—C22—C21	120.83 (14)
C17—C12—C11	122.32 (12)	C23—C22—C21	118.66 (13)
C17—C12—C13	120.82 (13)	O1—C1—C2	106.70 (10)
C19—C24—H24	120.7	O1—C1—C6	109.52 (11)
C23—C24—C19	118.64 (13)	O1—C1—H1	110.3
C23—C24—H24	120.7	C2—C1—C6	109.65 (10)
C4—C5—C6	121.44 (13)	C2—C1—H1	110.3
C10—C5—C4	118.62 (13)	C6—C1—H1	110.3
C10—C5—C6	119.92 (13)	C12—C17—H17	120.8
O1—C11—C12	112.13 (11)	C16—C17—C12	118.40 (14)
O2—C11—O1	124.43 (12)	C16—C17—H17	120.8
O2—C11—C12	123.44 (12)	C5—C10—H10	119.5
H3A—C3—H3B	107.9	C9—C10—C5	120.97 (15)
C2—C3—H3A	109.1	C9—C10—H10	119.5
C2—C3—H3B	109.1	F4—C21—C20	120.46 (13)
C4—C3—H3A	109.1	F4—C21—C22	118.31 (13)
C4—C3—H3B	109.1	C20—C21—C22	121.21 (14)
C4—C3—C2	112.34 (11)	F1—C14—C13	120.00 (18)
C19—C20—H20	120.3	F1—C14—C15	118.41 (15)
C21—C20—C19	119.45 (13)	C13—C14—C15	121.59 (15)
C21—C20—H20	120.3	C4—C7—H7	119.2
O3—C2—C3	110.04 (11)	C8—C7—C4	121.53 (16)
O3—C2—H2	108.8	C8—C7—H7	119.2
O3—C2—C1	108.10 (10)	C10—C9—H9	119.9
C3—C2—H2	108.8	C10—C9—C8	120.23 (16)
C1—C2—C3	112.14 (12)	C8—C9—H9	119.9
C1—C2—H2	108.8	F3—C16—C17	119.93 (17)
C5—C4—C3	121.48 (12)	F3—C16—C15	118.58 (15)
C7—C4—C5	119.30 (14)	C15—C16—C17	121.48 (16)
C7—C4—C3	119.21 (13)	F2—C15—C14	120.33 (18)
C5—C6—H6A	108.9	F2—C15—C16	120.66 (19)
C5—C6—H6B	108.9	C14—C15—C16	119.00 (14)
C5—C6—C1	113.52 (11)	C7—C8—C9	119.35 (16)
H6A—C6—H6B	107.7	C7—C8—H8	120.3
C1—C6—H6A	108.9	C9—C8—H8	120.3
F5—C22—C21—F4	−0.7 (2)	C3—C2—C1—C6	62.89 (15)
F5—C22—C21—C20	−179.19 (12)	C3—C4—C7—C8	−178.74 (16)
O3—C2—C1—O1	65.84 (13)	C20—C19—C18—O3	171.79 (11)
O3—C2—C1—C6	−175.63 (10)	C20—C19—C18—O4	−9.5 (2)
F6—C23—C22—F5	−0.7 (2)	C20—C19—C24—C23	0.1 (2)
F6—C23—C22—C21	179.36 (12)	C2—O3—C18—O4	−0.77 (19)
F1—C14—C15—F2	−0.7 (2)	C2—O3—C18—C19	177.94 (10)
F1—C14—C15—C16	178.44 (14)	C2—C3—C4—C5	16.95 (19)
F3—C16—C15—F2	−2.1 (2)	C2—C3—C4—C7	−164.32 (13)
F3—C16—C15—C14	178.82 (14)	C4—C5—C6—C1	17.94 (18)
C19—C24—C23—F6	−179.77 (12)	C4—C5—C10—C9	−0.2 (2)
C19—C24—C23—C22	0.5 (2)	C4—C3—C2—O3	−167.43 (10)
C19—C20—C21—F4	−178.61 (12)	C4—C3—C2—C1	−47.08 (15)
C19—C20—C21—C22	−0.1 (2)	C4—C7—C8—C9	0.1 (3)
C18—O3—C2—C3	−87.56 (14)	C6—C5—C4—C3	−2.7 (2)
C18—O3—C2—C1	149.68 (11)	C6—C5—C4—C7	178.61 (13)
C18—C19—C24—C23	−177.43 (12)	C6—C5—C10—C9	−178.81 (14)
C18—C19—C20—C21	177.37 (11)	C23—C22—C21—F4	179.20 (12)
C12—C13—C14—F1	−177.78 (12)	C23—C22—C21—C20	0.7 (2)
C12—C13—C14—C15	1.3 (2)	C13—C12—C11—O1	−177.72 (11)
C12—C17—C16—F3	−178.45 (13)	C13—C12—C11—O2	2.2 (2)
C12—C17—C16—C15	0.7 (2)	C13—C12—C17—C16	−0.04 (19)
C24—C19—C18—O3	−10.62 (18)	C13—C14—C15—F2	−179.84 (14)
C24—C19—C18—O4	168.10 (13)	C13—C14—C15—C16	−0.7 (2)
C24—C19—C20—C21	−0.3 (2)	C1—O1—C11—O2	0.8 (2)
C24—C23—C22—F5	179.02 (12)	C1—O1—C11—C12	−179.33 (10)
C24—C23—C22—C21	−0.9 (2)	C17—C12—C11—O1	2.15 (18)
C5—C4—C7—C8	0.0 (2)	C17—C12—C11—O2	−177.98 (14)
C5—C6—C1—O1	70.05 (14)	C17—C12—C13—C14	−1.0 (2)
C5—C6—C1—C2	−46.71 (15)	C17—C16—C15—F2	178.78 (14)
C5—C10—C9—C8	0.3 (3)	C17—C16—C15—C14	−0.4 (2)
C11—O1—C1—C2	−146.63 (11)	C10—C5—C4—C3	178.74 (13)
C11—O1—C1—C6	94.76 (13)	C10—C5—C4—C7	0.0 (2)
C11—C12—C13—C14	178.91 (12)	C10—C5—C6—C1	−163.47 (12)
C11—C12—C17—C16	−179.91 (13)	C10—C9—C8—C7	−0.3 (3)
C3—C2—C1—O1	−55.64 (14)

(2R,3S)-1,2,3,4-Tetrahydronaphthalene-2,3-diyl bis[4-(benzyloxy)benzoate] (7)

Crystal data

C38H32O6	Z = 4
Mr = 583.64	F(000) = 1232
Triclinic, P1	Dx = 1.267 Mg m^−3
a = 10.239 (4) Å	Mo Kα radiation, λ = 0.71075 Å
b = 13.056 (5) Å	Cell parameters from 7390 reflections
c = 23.923 (9) Å	θ = 3.1–27.5°
α = 86.992 (11)°	µ = 0.09 mm^−1
β = 89.198 (10)°	T = 193 K
γ = 73.621 (6)°	Prism, colourless
V = 3064 (2) Å^3	0.24 × 0.09 × 0.05 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	8408 reflections with I > 2σ(I)
dtprofit.ref scans	Rint = 0.043
Absorption correction: empirical (using intensity measurements) DTABSCOR	θmax = 27.4°, θmin = 3.1°
Tmin = 0.703, Tmax = 1.000	h = −13→13
31561 measured reflections	k = −16→16
13700 independent reflections	l = −30→30

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0593P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
13700 reflections	Δρmax = 0.29 e Å^−3
793 parameters	Δρmin = −0.24 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O7	1.30215 (11)	−0.17114 (8)	0.18042 (4)	0.0410 (3)
O4	1.35744 (11)	−0.76348 (9)	0.28689 (4)	0.0418 (3)
O10	1.34590 (10)	−0.24465 (9)	0.29203 (4)	0.0395 (3)
O1	1.33099 (12)	−0.66175 (9)	0.17978 (5)	0.0461 (3)
O9	0.97997 (11)	0.28329 (8)	0.07517 (4)	0.0445 (3)
O3	0.98629 (11)	−0.19994 (8)	0.09329 (5)	0.0436 (3)
O8	1.36254 (12)	−0.19406 (9)	0.08981 (5)	0.0494 (3)
O12	1.29915 (13)	0.08896 (10)	0.47780 (5)	0.0577 (3)
O6	1.28924 (13)	−0.42277 (10)	0.46894 (5)	0.0580 (3)
O2	1.42417 (14)	−0.65436 (10)	0.09425 (5)	0.0658 (4)
O5	1.12829 (13)	−0.70808 (12)	0.28649 (7)	0.0790 (5)
O11	1.12624 (14)	−0.22110 (13)	0.31493 (7)	0.0825 (5)
C42	1.56817 (16)	−0.45174 (12)	0.25791 (6)	0.0354 (4)
C55	1.16410 (15)	0.04151 (12)	0.15827 (6)	0.0345 (4)
H55	1.181481	0.015571	0.196071	0.041*
C54	1.08742 (15)	0.14664 (12)	0.14681 (7)	0.0365 (4)
H54	1.054425	0.192692	0.176463	0.044*
C17	1.16394 (15)	−0.45642 (13)	0.16580 (7)	0.0382 (4)
H17	1.165600	−0.494707	0.200792	0.046*
C53	1.05961 (15)	0.18359 (12)	0.09148 (7)	0.0365 (4)
C12	1.24863 (16)	−0.50380 (13)	0.12282 (7)	0.0382 (4)
C50	1.21564 (15)	−0.02614 (12)	0.11543 (6)	0.0350 (4)
C16	1.07677 (15)	−0.35359 (13)	0.15821 (7)	0.0384 (4)
H16	1.020548	−0.321103	0.188022	0.046*
C41	1.41567 (16)	−0.42973 (13)	0.26558 (7)	0.0398 (4)
H41A	1.396937	−0.444609	0.305433	0.048*
H41B	1.383940	−0.479861	0.243278	0.048*
C5	1.65081 (16)	−0.86808 (13)	0.23145 (6)	0.0391 (4)
C40	1.33373 (16)	−0.31617 (12)	0.24857 (6)	0.0365 (4)
H40	1.235938	−0.313242	0.243514	0.044*
C49	1.30041 (16)	−0.13783 (13)	0.12552 (6)	0.0367 (4)
C15	1.07280 (15)	−0.29877 (12)	0.10644 (7)	0.0357 (4)
C57	0.82961 (17)	0.45510 (12)	0.09047 (7)	0.0388 (4)
C39	1.38881 (16)	−0.27830 (12)	0.19482 (6)	0.0362 (4)
H39	1.382810	−0.326665	0.164492	0.043*
C13	1.24527 (16)	−0.44684 (13)	0.07152 (7)	0.0414 (4)
H13	1.303441	−0.478413	0.042030	0.050*
C45	1.65558 (17)	−0.54656 (13)	0.28116 (7)	0.0423 (4)
H45	1.618249	−0.594761	0.302643	0.051*
C43	1.62395 (16)	−0.38144 (13)	0.22658 (6)	0.0372 (4)
C4	1.59555 (17)	−0.94913 (13)	0.25136 (7)	0.0399 (4)
C14	1.15848 (16)	−0.34538 (13)	0.06325 (7)	0.0393 (4)
H14	1.156961	−0.307228	0.028229	0.047*
C3	1.44467 (17)	−0.93659 (13)	0.24740 (8)	0.0477 (4)
H3A	1.414082	−0.965071	0.282833	0.057*
H3B	1.428675	−0.980120	0.216943	0.057*
C19	0.78282 (16)	−0.05931 (13)	0.10716 (7)	0.0395 (4)
C51	1.18866 (17)	0.01284 (13)	0.06013 (7)	0.0435 (4)
H51	1.224015	−0.032500	0.030421	0.052*
C1	1.42235 (17)	−0.76865 (12)	0.19002 (7)	0.0414 (4)
H1	1.429360	−0.809565	0.155389	0.050*
C30	1.38587 (18)	−0.56450 (14)	0.41186 (7)	0.0457 (4)
H30	1.472101	−0.566606	0.426820	0.055*
C69	1.38105 (17)	−0.11439 (13)	0.37558 (7)	0.0431 (4)
H69	1.460557	−0.157949	0.358722	0.052*
C26	1.25104 (17)	−0.63374 (13)	0.34988 (7)	0.0428 (4)
C62	0.88798 (18)	0.52731 (13)	0.06345 (7)	0.0469 (4)
H62	0.984283	0.511658	0.061372	0.056*
C64	1.25335 (17)	−0.12349 (13)	0.36116 (7)	0.0421 (4)
C52	1.11124 (17)	0.11645 (13)	0.04810 (7)	0.0447 (4)
H52	1.093106	0.142044	0.010281	0.054*
C44	1.53543 (16)	−0.27678 (13)	0.20081 (7)	0.0423 (4)
H44A	1.571777	−0.263003	0.163473	0.051*
H44B	1.538902	−0.217776	0.224578	0.051*
C2	1.35909 (17)	−0.82188 (13)	0.23637 (7)	0.0410 (4)
H2	1.264226	−0.820125	0.225926	0.049*
C63	1.23324 (17)	−0.19997 (14)	0.32097 (7)	0.0446 (4)
C56	0.91774 (18)	0.35370 (13)	0.11835 (7)	0.0461 (4)
H56A	0.988640	0.369544	0.141345	0.055*
H56B	0.861915	0.319705	0.143095	0.055*
C7	1.68193 (18)	−1.04458 (14)	0.27392 (7)	0.0479 (4)
H7	1.644505	−1.099854	0.287609	0.057*
C25	1.23612 (18)	−0.70477 (14)	0.30538 (8)	0.0470 (4)
C11	1.34306 (18)	−0.61288 (13)	0.12934 (7)	0.0443 (4)
C6	1.56301 (17)	−0.76284 (13)	0.20629 (7)	0.0455 (4)
H6A	1.608796	−0.741853	0.172686	0.055*
H6B	1.553369	−0.706938	0.233699	0.055*
C46	1.79454 (18)	−0.57166 (14)	0.27361 (7)	0.0489 (5)
H46	1.852132	−0.636525	0.289625	0.059*
C31	1.37658 (17)	−0.63586 (13)	0.37236 (7)	0.0418 (4)
H31	1.456689	−0.686840	0.360451	0.050*
C68	1.39250 (18)	−0.04248 (14)	0.41418 (7)	0.0481 (4)
H68	1.479911	−0.037116	0.423873	0.058*
C60	0.6677 (2)	0.64563 (15)	0.04278 (8)	0.0597 (6)
H60	0.612368	0.711516	0.026897	0.072*
C48	1.76441 (17)	−0.40833 (15)	0.21906 (7)	0.0484 (4)
H48	1.802609	−0.361138	0.197197	0.058*
C47	1.84942 (18)	−0.50149 (15)	0.24247 (8)	0.0523 (5)
H47	1.945098	−0.517511	0.237290	0.063*
C10	1.79085 (18)	−0.88436 (16)	0.23504 (7)	0.0526 (5)
H10	1.828980	−0.829179	0.221834	0.063*
C67	1.27712 (19)	0.02214 (14)	0.43895 (7)	0.0488 (4)
C71	1.22504 (19)	0.22520 (14)	0.54373 (7)	0.0505 (5)
C8	1.82109 (19)	−1.06014 (16)	0.27670 (7)	0.0545 (5)
H8	1.878853	−1.125860	0.291719	0.065*
C61	0.8074 (2)	0.62206 (14)	0.03946 (8)	0.0575 (5)
H61	0.848203	0.671073	0.020639	0.069*
C33	1.2126 (2)	−0.28075 (15)	0.53154 (8)	0.0526 (5)
C27	1.13546 (19)	−0.55881 (15)	0.36822 (8)	0.0587 (5)
H27	1.049243	−0.556653	0.353234	0.070*
C29	1.26943 (19)	−0.48986 (14)	0.42965 (7)	0.0480 (4)
C65	1.13832 (19)	−0.05829 (16)	0.38625 (8)	0.0589 (5)
H65	1.050870	−0.063862	0.376790	0.071*
C9	1.87537 (19)	−0.97909 (17)	0.25741 (8)	0.0573 (5)
H9	1.970675	−0.988631	0.259570	0.069*
C24	0.8129 (2)	0.03632 (15)	0.09729 (7)	0.0537 (5)
H24	0.899744	0.042200	0.107418	0.064*
C58	0.68922 (19)	0.47900 (15)	0.09267 (8)	0.0551 (5)
H58	0.647759	0.429539	0.110653	0.066*
C28	1.14309 (19)	−0.48699 (16)	0.40797 (9)	0.0618 (6)
H28	1.062947	−0.436473	0.420211	0.074*
C59	0.6088 (2)	0.57436 (17)	0.06890 (9)	0.0640 (6)
H59	0.512399	0.590310	0.070725	0.077*
C20	0.6571 (2)	−0.06701 (18)	0.09220 (8)	0.0607 (5)
H20	0.635301	−0.132774	0.098295	0.073*
C66	1.14915 (19)	0.01453 (16)	0.42476 (8)	0.0608 (5)
H66	1.069781	0.058898	0.441316	0.073*
C18	0.8856 (2)	−0.15332 (15)	0.13403 (8)	0.0616 (6)
H18A	0.929633	−0.130238	0.165753	0.074*
H18B	0.840217	−0.206844	0.148689	0.074*
C32	1.1706 (2)	−0.34744 (16)	0.48963 (9)	0.0639 (6)
H32A	1.109009	−0.385758	0.507570	0.077*
H32B	1.121095	−0.300791	0.458243	0.077*
C23	0.7201 (3)	0.12221 (16)	0.07330 (8)	0.0756 (7)
H23	0.742923	0.187467	0.066622	0.091*
C34	1.1549 (2)	−0.26955 (17)	0.58394 (9)	0.0671 (6)
H34	1.092102	−0.308466	0.594601	0.080*
C38	1.3058 (2)	−0.22467 (17)	0.51726 (8)	0.0653 (6)
H38	1.347273	−0.231381	0.481362	0.078*
C72	1.1714 (2)	0.23820 (17)	0.59652 (8)	0.0677 (6)
H72	1.110213	0.198928	0.608861	0.081*
C36	1.2773 (2)	−0.14701 (17)	0.60680 (9)	0.0693 (6)
H36	1.298025	−0.100350	0.632272	0.083*
C37	1.3388 (2)	−0.15890 (17)	0.55496 (9)	0.0709 (6)
H37	1.403981	−0.121821	0.545052	0.085*
C70	1.1817 (2)	0.15459 (16)	0.50475 (9)	0.0636 (6)
H70A	1.133799	0.108940	0.525999	0.076*
H70B	1.118217	0.198964	0.476290	0.076*
C35	1.1860 (3)	−0.20323 (18)	0.62126 (9)	0.0753 (7)
H35	1.144244	−0.196348	0.657103	0.090*
C76	1.3141 (2)	0.28247 (17)	0.52638 (9)	0.0703 (6)
H76	1.352660	0.274192	0.489965	0.084*
C21	0.5617 (2)	0.0217 (3)	0.06808 (9)	0.0868 (9)
H21	0.474030	0.017218	0.058142	0.104*
C22	0.5956 (3)	0.1161 (2)	0.05876 (9)	0.0876 (10)
H22	0.531268	0.176941	0.042101	0.105*
C73	1.2037 (3)	0.3063 (2)	0.63190 (9)	0.0839 (8)
H73	1.165671	0.313476	0.668422	0.101*
C74	1.2910 (3)	0.36416 (18)	0.61468 (11)	0.0831 (8)
H74	1.312628	0.412403	0.638925	0.100*
C75	1.3476 (3)	0.35175 (18)	0.56159 (11)	0.0854 (7)
H75	1.409155	0.390801	0.549465	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.0477 (7)	0.0300 (6)	0.0368 (6)	0.0032 (5)	−0.0015 (5)	−0.0013 (5)
O4	0.0368 (6)	0.0442 (7)	0.0406 (6)	−0.0042 (5)	−0.0027 (5)	−0.0069 (5)
O10	0.0377 (6)	0.0425 (7)	0.0373 (6)	−0.0083 (5)	0.0005 (5)	−0.0106 (5)
O1	0.0559 (7)	0.0321 (6)	0.0401 (7)	0.0039 (5)	−0.0030 (5)	−0.0002 (5)
O9	0.0536 (7)	0.0294 (6)	0.0414 (7)	0.0029 (5)	0.0031 (5)	−0.0002 (5)
O3	0.0459 (7)	0.0334 (6)	0.0438 (7)	0.0015 (5)	0.0041 (5)	−0.0022 (5)
O8	0.0572 (8)	0.0375 (7)	0.0408 (7)	0.0074 (6)	0.0051 (5)	−0.0041 (5)
O12	0.0542 (8)	0.0544 (8)	0.0633 (8)	−0.0090 (6)	0.0032 (6)	−0.0278 (7)
O6	0.0558 (8)	0.0523 (8)	0.0617 (8)	−0.0050 (6)	−0.0019 (6)	−0.0203 (7)
O2	0.0819 (10)	0.0482 (8)	0.0463 (8)	0.0157 (7)	0.0081 (7)	−0.0030 (6)
O5	0.0378 (8)	0.0858 (11)	0.1105 (12)	−0.0050 (7)	−0.0067 (7)	−0.0468 (9)
O11	0.0392 (8)	0.0985 (12)	0.1140 (13)	−0.0167 (8)	0.0096 (8)	−0.0625 (10)
C42	0.0382 (9)	0.0335 (9)	0.0333 (8)	−0.0072 (7)	−0.0033 (7)	−0.0061 (7)
C55	0.0342 (9)	0.0333 (9)	0.0339 (8)	−0.0059 (7)	−0.0030 (6)	−0.0032 (7)
C54	0.0364 (9)	0.0326 (9)	0.0384 (9)	−0.0056 (7)	−0.0017 (7)	−0.0048 (7)
C17	0.0356 (9)	0.0370 (9)	0.0387 (9)	−0.0046 (7)	−0.0056 (7)	−0.0015 (7)
C53	0.0353 (9)	0.0274 (8)	0.0430 (9)	−0.0028 (7)	0.0018 (7)	0.0002 (7)
C12	0.0379 (9)	0.0332 (9)	0.0406 (9)	−0.0046 (7)	−0.0063 (7)	−0.0049 (7)
C50	0.0312 (8)	0.0319 (9)	0.0383 (9)	−0.0028 (7)	−0.0002 (6)	−0.0024 (7)
C16	0.0350 (9)	0.0385 (9)	0.0373 (9)	−0.0030 (7)	−0.0015 (7)	−0.0043 (7)
C41	0.0419 (10)	0.0341 (9)	0.0430 (9)	−0.0106 (7)	−0.0023 (7)	0.0015 (7)
C5	0.0401 (10)	0.0411 (10)	0.0323 (8)	−0.0044 (8)	0.0009 (7)	−0.0068 (7)
C40	0.0368 (9)	0.0353 (9)	0.0369 (9)	−0.0084 (7)	−0.0037 (7)	−0.0051 (7)
C49	0.0370 (9)	0.0339 (9)	0.0358 (9)	−0.0040 (7)	−0.0025 (7)	−0.0026 (7)
C15	0.0339 (9)	0.0294 (8)	0.0417 (9)	−0.0051 (7)	−0.0041 (7)	−0.0039 (7)
C57	0.0415 (10)	0.0282 (9)	0.0434 (9)	−0.0037 (7)	−0.0004 (7)	−0.0055 (7)
C39	0.0422 (9)	0.0248 (8)	0.0362 (9)	−0.0004 (7)	−0.0028 (7)	−0.0019 (7)
C13	0.0436 (10)	0.0378 (9)	0.0393 (9)	−0.0047 (8)	0.0014 (7)	−0.0081 (8)
C45	0.0476 (10)	0.0349 (9)	0.0414 (9)	−0.0059 (8)	−0.0048 (7)	−0.0038 (8)
C43	0.0387 (9)	0.0360 (9)	0.0354 (9)	−0.0074 (7)	−0.0020 (7)	−0.0047 (7)
C4	0.0442 (10)	0.0355 (9)	0.0360 (9)	−0.0038 (8)	−0.0041 (7)	−0.0064 (7)
C14	0.0440 (10)	0.0339 (9)	0.0372 (9)	−0.0064 (7)	−0.0005 (7)	−0.0012 (7)
C3	0.0482 (11)	0.0336 (9)	0.0591 (11)	−0.0069 (8)	−0.0125 (8)	−0.0030 (8)
C19	0.0375 (9)	0.0343 (9)	0.0405 (9)	0.0000 (7)	0.0041 (7)	−0.0043 (7)
C51	0.0472 (10)	0.0359 (9)	0.0383 (9)	0.0029 (8)	0.0047 (7)	−0.0034 (8)
C1	0.0477 (10)	0.0297 (9)	0.0389 (9)	0.0030 (7)	−0.0057 (7)	−0.0051 (7)
C30	0.0422 (10)	0.0452 (10)	0.0466 (10)	−0.0073 (8)	−0.0028 (8)	−0.0014 (8)
C69	0.0412 (10)	0.0411 (10)	0.0440 (10)	−0.0064 (8)	0.0050 (7)	−0.0058 (8)
C26	0.0424 (10)	0.0365 (9)	0.0465 (10)	−0.0061 (8)	0.0007 (8)	−0.0031 (8)
C62	0.0432 (10)	0.0374 (10)	0.0593 (11)	−0.0098 (8)	−0.0074 (8)	−0.0013 (9)
C64	0.0390 (10)	0.0400 (10)	0.0440 (10)	−0.0048 (8)	−0.0020 (7)	−0.0081 (8)
C52	0.0518 (11)	0.0391 (10)	0.0348 (9)	0.0002 (8)	0.0031 (7)	0.0016 (8)
C44	0.0438 (10)	0.0367 (9)	0.0442 (10)	−0.0086 (8)	0.0012 (7)	0.0033 (8)
C2	0.0404 (9)	0.0356 (9)	0.0447 (10)	−0.0056 (7)	−0.0099 (7)	−0.0063 (8)
C63	0.0347 (10)	0.0426 (10)	0.0507 (11)	−0.0001 (8)	−0.0004 (8)	−0.0090 (8)
C56	0.0533 (11)	0.0307 (9)	0.0473 (10)	0.0003 (8)	0.0040 (8)	−0.0070 (8)
C7	0.0506 (11)	0.0404 (10)	0.0457 (10)	−0.0011 (8)	−0.0034 (8)	−0.0029 (8)
C25	0.0353 (10)	0.0419 (10)	0.0575 (11)	−0.0007 (8)	0.0011 (8)	−0.0025 (9)
C11	0.0523 (11)	0.0350 (9)	0.0386 (10)	−0.0003 (8)	−0.0056 (8)	−0.0042 (8)
C6	0.0505 (11)	0.0384 (10)	0.0451 (10)	−0.0085 (8)	0.0022 (8)	−0.0025 (8)
C46	0.0489 (11)	0.0395 (10)	0.0494 (11)	0.0031 (9)	−0.0078 (8)	−0.0071 (8)
C31	0.0395 (9)	0.0378 (10)	0.0431 (10)	−0.0034 (8)	0.0033 (7)	0.0018 (8)
C68	0.0430 (10)	0.0479 (11)	0.0540 (11)	−0.0118 (8)	0.0009 (8)	−0.0139 (9)
C60	0.0697 (14)	0.0372 (11)	0.0577 (12)	0.0111 (10)	−0.0187 (10)	−0.0102 (9)
C48	0.0411 (10)	0.0529 (11)	0.0492 (11)	−0.0110 (9)	0.0002 (8)	0.0018 (9)
C47	0.0360 (10)	0.0592 (12)	0.0552 (11)	−0.0026 (9)	−0.0007 (8)	−0.0047 (10)
C10	0.0448 (11)	0.0649 (13)	0.0449 (10)	−0.0106 (10)	0.0065 (8)	−0.0012 (9)
C67	0.0528 (11)	0.0431 (10)	0.0485 (11)	−0.0078 (9)	−0.0002 (8)	−0.0157 (9)
C71	0.0616 (12)	0.0408 (10)	0.0431 (10)	−0.0032 (9)	−0.0022 (9)	−0.0094 (8)
C8	0.0494 (12)	0.0557 (12)	0.0434 (10)	0.0096 (10)	−0.0027 (8)	−0.0022 (9)
C61	0.0773 (15)	0.0340 (10)	0.0618 (13)	−0.0166 (10)	−0.0137 (10)	0.0025 (9)
C33	0.0610 (12)	0.0423 (11)	0.0460 (11)	0.0007 (9)	−0.0044 (9)	−0.0071 (9)
C27	0.0383 (10)	0.0585 (13)	0.0737 (14)	−0.0014 (9)	−0.0032 (9)	−0.0198 (11)
C29	0.0526 (11)	0.0400 (10)	0.0484 (11)	−0.0072 (9)	−0.0004 (8)	−0.0064 (8)
C65	0.0405 (11)	0.0619 (13)	0.0703 (13)	−0.0030 (9)	−0.0025 (9)	−0.0291 (10)
C9	0.0385 (10)	0.0775 (15)	0.0466 (11)	−0.0012 (10)	0.0013 (8)	−0.0022 (10)
C24	0.0678 (13)	0.0499 (12)	0.0492 (11)	−0.0255 (10)	−0.0082 (9)	−0.0023 (9)
C58	0.0471 (11)	0.0520 (12)	0.0615 (12)	−0.0068 (9)	0.0093 (9)	−0.0030 (10)
C28	0.0446 (11)	0.0575 (13)	0.0761 (14)	0.0012 (9)	0.0009 (10)	−0.0247 (11)
C59	0.0411 (11)	0.0666 (14)	0.0702 (14)	0.0101 (10)	−0.0033 (9)	−0.0152 (11)
C20	0.0574 (13)	0.0726 (14)	0.0594 (13)	−0.0303 (11)	0.0085 (10)	−0.0059 (11)
C66	0.0437 (11)	0.0612 (13)	0.0711 (13)	0.0008 (9)	0.0025 (9)	−0.0319 (11)
C18	0.0622 (13)	0.0520 (12)	0.0506 (11)	0.0147 (10)	0.0142 (9)	0.0018 (9)
C32	0.0600 (13)	0.0565 (13)	0.0698 (14)	−0.0039 (10)	0.0039 (10)	−0.0239 (11)
C23	0.133 (2)	0.0329 (11)	0.0499 (13)	−0.0053 (13)	−0.0047 (13)	−0.0053 (9)
C34	0.0826 (16)	0.0587 (13)	0.0582 (13)	−0.0163 (12)	0.0087 (11)	−0.0099 (11)
C38	0.0835 (16)	0.0672 (14)	0.0475 (12)	−0.0242 (12)	0.0012 (10)	−0.0071 (10)
C72	0.0803 (15)	0.0706 (15)	0.0495 (12)	−0.0148 (12)	0.0077 (10)	−0.0150 (11)
C36	0.0965 (18)	0.0491 (13)	0.0521 (13)	−0.0015 (12)	−0.0192 (12)	−0.0108 (10)
C37	0.0914 (17)	0.0627 (14)	0.0636 (14)	−0.0291 (13)	−0.0116 (12)	−0.0058 (11)
C70	0.0613 (13)	0.0608 (13)	0.0668 (13)	−0.0097 (10)	0.0068 (10)	−0.0302 (11)
C35	0.1061 (19)	0.0678 (15)	0.0482 (13)	−0.0171 (14)	0.0050 (12)	−0.0115 (11)
C76	0.1069 (19)	0.0612 (14)	0.0491 (12)	−0.0326 (13)	0.0052 (11)	−0.0102 (10)
C21	0.0318 (11)	0.157 (3)	0.0593 (14)	−0.0061 (15)	−0.0006 (9)	−0.0111 (17)
C22	0.092 (2)	0.0834 (19)	0.0415 (12)	0.0501 (16)	0.0033 (12)	−0.0031 (12)
C73	0.105 (2)	0.0867 (19)	0.0484 (13)	−0.0037 (16)	−0.0043 (12)	−0.0253 (13)
C74	0.108 (2)	0.0549 (15)	0.0754 (17)	0.0016 (14)	−0.0361 (15)	−0.0293 (12)
C75	0.118 (2)	0.0618 (15)	0.0850 (18)	−0.0371 (15)	−0.0089 (15)	−0.0115 (13)

Geometric parameters (Å, º)

O7—C49	1.3604 (18)	C62—H62	0.9500
O7—C39	1.4565 (17)	C62—C61	1.380 (2)
O4—C2	1.4598 (19)	C64—C63	1.479 (2)
O4—C25	1.3452 (19)	C64—C65	1.393 (2)
O10—C40	1.4628 (18)	C52—H52	0.9500
O10—C63	1.3382 (19)	C44—H44A	0.9900
O1—C1	1.4551 (18)	C44—H44B	0.9900
O1—C11	1.356 (2)	C2—H2	1.0000
O9—C53	1.3669 (18)	C56—H56A	0.9900
O9—C56	1.4386 (19)	C56—H56B	0.9900
O3—C15	1.3671 (18)	C7—H7	0.9500
O3—C18	1.436 (2)	C7—C8	1.383 (3)
O8—C49	1.2084 (18)	C6—H6A	0.9900
O12—C67	1.370 (2)	C6—H6B	0.9900
O12—C70	1.432 (2)	C46—H46	0.9500
O6—C29	1.373 (2)	C46—C47	1.385 (3)
O6—C32	1.431 (2)	C31—H31	0.9500
O2—C11	1.209 (2)	C68—H68	0.9500
O5—C25	1.212 (2)	C68—C67	1.389 (2)
O11—C63	1.215 (2)	C60—H60	0.9500
C42—C41	1.516 (2)	C60—C61	1.377 (3)
C42—C45	1.400 (2)	C60—C59	1.366 (3)
C42—C43	1.394 (2)	C48—H48	0.9500
C55—H55	0.9500	C48—C47	1.377 (2)
C55—C54	1.391 (2)	C47—H47	0.9500
C55—C50	1.388 (2)	C10—H10	0.9500
C54—H54	0.9500	C10—C9	1.380 (2)
C54—C53	1.390 (2)	C67—C66	1.390 (3)
C17—H17	0.9500	C71—C72	1.370 (3)
C17—C12	1.390 (2)	C71—C70	1.500 (3)
C17—C16	1.391 (2)	C71—C76	1.380 (3)
C53—C52	1.394 (2)	C8—H8	0.9500
C12—C13	1.397 (2)	C8—C9	1.384 (3)
C12—C11	1.480 (2)	C61—H61	0.9500
C50—C49	1.481 (2)	C33—C32	1.505 (3)
C50—C51	1.395 (2)	C33—C34	1.376 (3)
C16—H16	0.9500	C33—C38	1.386 (3)
C16—C15	1.393 (2)	C27—H27	0.9500
C41—H41A	0.9900	C27—C28	1.388 (3)
C41—H41B	0.9900	C29—C28	1.390 (3)
C41—C40	1.521 (2)	C65—H65	0.9500
C5—C4	1.394 (2)	C65—C66	1.385 (3)
C5—C6	1.513 (2)	C9—H9	0.9500
C5—C10	1.392 (2)	C24—H24	0.9500
C40—H40	1.0000	C24—C23	1.355 (3)
C40—C39	1.512 (2)	C58—H58	0.9500
C15—C14	1.395 (2)	C58—C59	1.383 (3)
C57—C62	1.381 (2)	C28—H28	0.9500
C57—C56	1.504 (2)	C59—H59	0.9500
C57—C58	1.383 (2)	C20—H20	0.9500
C39—H39	1.0000	C20—C21	1.391 (3)
C39—C44	1.516 (2)	C66—H66	0.9500
C13—H13	0.9500	C18—H18A	0.9900
C13—C14	1.377 (2)	C18—H18B	0.9900
C45—H45	0.9500	C32—H32A	0.9900
C45—C46	1.379 (2)	C32—H32B	0.9900
C43—C44	1.516 (2)	C23—H23	0.9500
C43—C48	1.392 (2)	C23—C22	1.352 (4)
C4—C3	1.511 (2)	C34—H34	0.9500
C4—C7	1.396 (2)	C34—C35	1.376 (3)
C14—H14	0.9500	C38—H38	0.9500
C3—H3A	0.9900	C38—C37	1.385 (3)
C3—H3B	0.9900	C72—H72	0.9500
C3—C2	1.518 (2)	C72—C73	1.367 (3)
C19—C24	1.376 (2)	C36—H36	0.9500
C19—C20	1.373 (3)	C36—C37	1.379 (3)
C19—C18	1.495 (2)	C36—C35	1.373 (3)
C51—H51	0.9500	C37—H37	0.9500
C51—C52	1.379 (2)	C70—H70A	0.9900
C1—H1	1.0000	C70—H70B	0.9900
C1—C2	1.512 (2)	C35—H35	0.9500
C1—C6	1.520 (2)	C76—H76	0.9500
C30—H30	0.9500	C76—C75	1.381 (3)
C30—C31	1.384 (2)	C21—H21	0.9500
C30—C29	1.388 (2)	C21—C22	1.378 (4)
C69—H69	0.9500	C22—H22	0.9500
C69—C64	1.395 (2)	C73—H73	0.9500
C69—C68	1.380 (2)	C73—C74	1.370 (4)
C26—C25	1.485 (2)	C74—H74	0.9500
C26—C31	1.393 (2)	C74—C75	1.387 (3)
C26—C27	1.388 (2)	C75—H75	0.9500
C49—O7—C39	116.14 (11)	C8—C7—H7	119.4
C25—O4—C2	117.75 (13)	O4—C25—C26	111.96 (15)
C63—O10—C40	116.97 (13)	O5—C25—O4	123.38 (17)
C11—O1—C1	116.15 (12)	O5—C25—C26	124.63 (16)
C53—O9—C56	117.60 (12)	O1—C11—C12	112.68 (14)
C15—O3—C18	117.72 (12)	O2—C11—O1	122.94 (15)
C67—O12—C70	117.03 (15)	O2—C11—C12	124.38 (16)
C29—O6—C32	117.04 (15)	C5—C6—C1	112.42 (14)
C45—C42—C41	119.56 (15)	C5—C6—H6A	109.1
C43—C42—C41	121.62 (14)	C5—C6—H6B	109.1
C43—C42—C45	118.78 (15)	C1—C6—H6A	109.1
C54—C55—H55	119.4	C1—C6—H6B	109.1
C50—C55—H55	119.4	H6A—C6—H6B	107.9
C50—C55—C54	121.12 (14)	C45—C46—H46	120.3
C55—C54—H54	120.4	C45—C46—C47	119.42 (16)
C53—C54—C55	119.27 (14)	C47—C46—H46	120.3
C53—C54—H54	120.4	C30—C31—C26	120.71 (16)
C12—C17—H17	119.6	C30—C31—H31	119.6
C12—C17—C16	120.79 (15)	C26—C31—H31	119.6
C16—C17—H17	119.6	C69—C68—H68	119.8
O9—C53—C54	124.56 (14)	C69—C68—C67	120.46 (17)
O9—C53—C52	115.33 (14)	C67—C68—H68	119.8
C54—C53—C52	120.09 (14)	C61—C60—H60	120.0
C17—C12—C13	119.15 (15)	C59—C60—H60	120.0
C17—C12—C11	122.38 (15)	C59—C60—C61	120.07 (18)
C13—C12—C11	118.48 (15)	C43—C48—H48	119.1
C55—C50—C49	123.10 (14)	C47—C48—C43	121.76 (17)
C55—C50—C51	118.82 (14)	C47—C48—H48	119.1
C51—C50—C49	118.07 (14)	C46—C47—H47	120.2
C17—C16—H16	120.4	C48—C47—C46	119.56 (17)
C17—C16—C15	119.30 (15)	C48—C47—H47	120.2
C15—C16—H16	120.4	C5—C10—H10	119.4
C42—C41—H41A	108.6	C9—C10—C5	121.29 (18)
C42—C41—H41B	108.6	C9—C10—H10	119.4
C42—C41—C40	114.49 (13)	O12—C67—C68	116.13 (16)
H41A—C41—H41B	107.6	O12—C67—C66	124.00 (16)
C40—C41—H41A	108.6	C68—C67—C66	119.85 (17)
C40—C41—H41B	108.6	C72—C71—C70	120.4 (2)
C4—C5—C6	121.94 (15)	C72—C71—C76	118.62 (19)
C10—C5—C4	118.99 (16)	C76—C71—C70	120.92 (18)
C10—C5—C6	119.07 (16)	C7—C8—H8	120.3
O10—C40—C41	109.32 (12)	C7—C8—C9	119.39 (17)
O10—C40—H40	109.8	C9—C8—H8	120.3
O10—C40—C39	107.61 (13)	C62—C61—H61	120.0
C41—C40—H40	109.8	C60—C61—C62	120.04 (18)
C39—C40—C41	110.45 (13)	C60—C61—H61	120.0
C39—C40—H40	109.8	C34—C33—C32	121.0 (2)
O7—C49—C50	112.24 (13)	C34—C33—C38	118.26 (19)
O8—C49—O7	122.88 (14)	C38—C33—C32	120.64 (18)
O8—C49—C50	124.87 (14)	C26—C27—H27	119.3
O3—C15—C16	124.38 (14)	C28—C27—C26	121.46 (18)
O3—C15—C14	115.36 (14)	C28—C27—H27	119.3
C16—C15—C14	120.23 (14)	O6—C29—C30	115.70 (16)
C62—C57—C56	120.30 (15)	O6—C29—C28	124.29 (16)
C62—C57—C58	118.90 (16)	C30—C29—C28	120.01 (18)
C58—C57—C56	120.78 (16)	C64—C65—H65	119.4
O7—C39—C40	106.98 (12)	C66—C65—C64	121.19 (18)
O7—C39—H39	109.2	C66—C65—H65	119.4
O7—C39—C44	110.28 (13)	C10—C9—C8	119.90 (18)
C40—C39—H39	109.2	C10—C9—H9	120.0
C40—C39—C44	112.07 (13)	C8—C9—H9	120.0
C44—C39—H39	109.2	C19—C24—H24	119.6
C12—C13—H13	119.7	C23—C24—C19	120.9 (2)
C14—C13—C12	120.67 (15)	C23—C24—H24	119.6
C14—C13—H13	119.7	C57—C58—H58	119.8
C42—C45—H45	119.2	C59—C58—C57	120.49 (19)
C46—C45—C42	121.56 (16)	C59—C58—H58	119.8
C46—C45—H45	119.2	C27—C28—C29	119.21 (18)
C42—C43—C44	121.56 (14)	C27—C28—H28	120.4
C48—C43—C42	118.92 (15)	C29—C28—H28	120.4
C48—C43—C44	119.53 (15)	C60—C59—C58	120.05 (19)
C5—C4—C3	121.18 (14)	C60—C59—H59	120.0
C5—C4—C7	119.25 (16)	C58—C59—H59	120.0
C7—C4—C3	119.55 (16)	C19—C20—H20	120.1
C15—C14—H14	120.1	C19—C20—C21	119.9 (2)
C13—C14—C15	119.84 (15)	C21—C20—H20	120.1
C13—C14—H14	120.1	C67—C66—H66	120.3
C4—C3—H3A	108.8	C65—C66—C67	119.44 (17)
C4—C3—H3B	108.8	C65—C66—H66	120.3
C4—C3—C2	113.87 (14)	O3—C18—C19	109.17 (14)
H3A—C3—H3B	107.7	O3—C18—H18A	109.8
C2—C3—H3A	108.8	O3—C18—H18B	109.8
C2—C3—H3B	108.8	C19—C18—H18A	109.8
C24—C19—C18	120.37 (17)	C19—C18—H18B	109.8
C20—C19—C24	119.08 (17)	H18A—C18—H18B	108.3
C20—C19—C18	120.54 (18)	O6—C32—C33	109.29 (16)
C50—C51—H51	119.6	O6—C32—H32A	109.8
C52—C51—C50	120.74 (15)	O6—C32—H32B	109.8
C52—C51—H51	119.6	C33—C32—H32A	109.8
O1—C1—H1	109.4	C33—C32—H32B	109.8
O1—C1—C2	106.62 (13)	H32A—C32—H32B	108.3
O1—C1—C6	110.43 (14)	C24—C23—H23	119.6
C2—C1—H1	109.4	C22—C23—C24	120.7 (2)
C2—C1—C6	111.46 (13)	C22—C23—H23	119.6
C6—C1—H1	109.4	C33—C34—H34	119.3
C31—C30—H30	119.9	C33—C34—C35	121.5 (2)
C31—C30—C29	120.11 (17)	C35—C34—H34	119.3
C29—C30—H30	119.9	C33—C38—H38	119.8
C64—C69—H69	119.8	C37—C38—C33	120.5 (2)
C68—C69—H69	119.8	C37—C38—H38	119.8
C68—C69—C64	120.37 (16)	C71—C72—H72	119.2
C31—C26—C25	122.89 (15)	C73—C72—C71	121.6 (2)
C27—C26—C25	118.56 (16)	C73—C72—H72	119.2
C27—C26—C31	118.49 (17)	C37—C36—H36	120.3
C57—C62—H62	119.8	C35—C36—H36	120.3
C61—C62—C57	120.43 (17)	C35—C36—C37	119.4 (2)
C61—C62—H62	119.8	C38—C37—H37	119.9
C69—C64—C63	123.45 (15)	C36—C37—C38	120.3 (2)
C65—C64—C69	118.68 (16)	C36—C37—H37	119.9
C65—C64—C63	117.87 (16)	O12—C70—C71	109.40 (16)
C53—C52—H52	120.0	O12—C70—H70A	109.8
C51—C52—C53	119.94 (15)	O12—C70—H70B	109.8
C51—C52—H52	120.0	C71—C70—H70A	109.8
C39—C44—H44A	109.3	C71—C70—H70B	109.8
C39—C44—H44B	109.3	H70A—C70—H70B	108.2
C43—C44—C39	111.81 (13)	C34—C35—H35	119.9
C43—C44—H44A	109.3	C36—C35—C34	120.1 (2)
C43—C44—H44B	109.3	C36—C35—H35	119.9
H44A—C44—H44B	107.9	C71—C76—H76	119.8
O4—C2—C3	108.73 (13)	C71—C76—C75	120.4 (2)
O4—C2—C1	107.79 (13)	C75—C76—H76	119.8
O4—C2—H2	110.1	C20—C21—H21	120.3
C3—C2—H2	110.1	C22—C21—C20	119.4 (2)
C1—C2—C3	109.92 (14)	C22—C21—H21	120.3
C1—C2—H2	110.1	C23—C22—C21	120.1 (2)
O10—C63—C64	112.96 (15)	C23—C22—H22	120.0
O11—C63—O10	123.17 (16)	C21—C22—H22	120.0
O11—C63—C64	123.87 (16)	C72—C73—H73	120.0
O9—C56—C57	107.86 (13)	C72—C73—C74	120.0 (2)
O9—C56—H56A	110.1	C74—C73—H73	120.0
O9—C56—H56B	110.1	C73—C74—H74	120.3
C57—C56—H56A	110.1	C73—C74—C75	119.5 (2)
C57—C56—H56B	110.1	C75—C74—H74	120.3
H56A—C56—H56B	108.4	C76—C75—C74	119.8 (2)
C4—C7—H7	119.4	C76—C75—H75	120.1
C8—C7—C4	121.17 (18)	C74—C75—H75	120.1
O7—C39—C44—C43	168.91 (12)	C64—C69—C68—C67	−0.3 (3)
O10—C40—C39—O7	−62.81 (15)	C64—C65—C66—C67	−0.5 (3)
O10—C40—C39—C44	58.18 (16)	C44—C43—C48—C47	178.78 (16)
O1—C1—C2—O4	−64.81 (15)	C2—O4—C25—O5	9.2 (3)
O1—C1—C2—C3	176.83 (13)	C2—O4—C25—C26	−168.90 (13)
O1—C1—C6—C5	165.40 (13)	C2—C1—C6—C5	47.07 (18)
O9—C53—C52—C51	−177.61 (15)	C63—O10—C40—C41	−112.87 (15)
O3—C15—C14—C13	−177.18 (14)	C63—O10—C40—C39	127.15 (14)
O12—C67—C66—C65	−177.83 (18)	C63—C64—C65—C66	179.33 (18)
O6—C29—C28—C27	179.87 (18)	C56—O9—C53—C54	−1.8 (2)
C42—C41—C40—O10	−76.69 (17)	C56—O9—C53—C52	176.53 (15)
C42—C41—C40—C39	41.53 (18)	C56—C57—C62—C61	−177.81 (16)
C42—C45—C46—C47	0.2 (3)	C56—C57—C58—C59	177.38 (16)
C42—C43—C44—C39	−20.8 (2)	C7—C4—C3—C2	165.19 (15)
C42—C43—C48—C47	−1.0 (3)	C7—C8—C9—C10	−0.8 (3)
C55—C54—C53—O9	176.59 (14)	C25—O4—C2—C3	−131.03 (15)
C55—C54—C53—C52	−1.6 (2)	C25—O4—C2—C1	109.85 (15)
C55—C50—C49—O7	10.4 (2)	C25—C26—C31—C30	176.86 (16)
C55—C50—C49—O8	−169.08 (16)	C25—C26—C27—C28	−177.23 (18)
C55—C50—C51—C52	−0.5 (2)	C11—O1—C1—C2	−159.40 (14)
C54—C55—C50—C49	178.54 (14)	C11—O1—C1—C6	79.36 (17)
C54—C55—C50—C51	−0.4 (2)	C11—C12—C13—C14	179.55 (15)
C54—C53—C52—C51	0.8 (3)	C6—C5—C4—C3	1.5 (2)
C17—C12—C13—C14	−0.6 (2)	C6—C5—C4—C7	179.77 (14)
C17—C12—C11—O1	3.7 (2)	C6—C5—C10—C9	−179.73 (16)
C17—C12—C11—O2	−175.24 (18)	C6—C1—C2—O4	55.78 (17)
C17—C16—C15—O3	176.41 (14)	C6—C1—C2—C3	−62.59 (18)
C17—C16—C15—C14	−2.0 (2)	C31—C30—C29—O6	179.92 (15)
C53—O9—C56—C57	−176.79 (13)	C31—C30—C29—C28	0.3 (3)
C12—C17—C16—C15	1.3 (2)	C31—C26—C25—O4	−5.1 (2)
C12—C13—C14—C15	−0.1 (2)	C31—C26—C25—O5	176.89 (18)
C50—C55—C54—C53	1.4 (2)	C31—C26—C27—C28	0.1 (3)
C50—C51—C52—C53	0.3 (3)	C68—C69—C64—C63	−178.87 (16)
C16—C17—C12—C13	−0.1 (2)	C68—C69—C64—C65	0.3 (3)
C16—C17—C12—C11	179.80 (15)	C68—C67—C66—C65	0.5 (3)
C16—C15—C14—C13	1.3 (2)	C48—C43—C44—C39	159.36 (15)
C41—C42—C45—C46	177.71 (15)	C10—C5—C4—C3	−178.72 (15)
C41—C42—C43—C44	2.9 (2)	C10—C5—C4—C7	−0.5 (2)
C41—C42—C43—C48	−177.26 (15)	C10—C5—C6—C1	163.52 (15)
C41—C40—C39—O7	177.92 (12)	C67—O12—C70—C71	−177.57 (16)
C41—C40—C39—C44	−61.09 (17)	C71—C72—C73—C74	0.5 (4)
C5—C4—C3—C2	−16.6 (2)	C71—C76—C75—C74	−0.2 (4)
C5—C4—C7—C8	−0.2 (2)	C61—C60—C59—C58	0.8 (3)
C5—C10—C9—C8	0.1 (3)	C33—C34—C35—C36	−0.5 (3)
C40—O10—C63—O11	4.5 (2)	C33—C38—C37—C36	−1.2 (3)
C40—O10—C63—C64	−176.07 (13)	C27—C26—C25—O4	172.13 (16)
C40—C39—C44—C43	49.85 (18)	C27—C26—C25—O5	−5.9 (3)
C49—O7—C39—C40	−156.72 (13)	C27—C26—C31—C30	−0.3 (3)
C49—O7—C39—C44	81.17 (16)	C29—O6—C32—C33	−179.42 (16)
C49—C50—C51—C52	−179.49 (16)	C29—C30—C31—C26	0.2 (3)
C15—O3—C18—C19	−167.01 (14)	C65—C64—C63—O10	168.78 (16)
C57—C62—C61—C60	0.6 (3)	C65—C64—C63—O11	−11.8 (3)
C57—C58—C59—C60	0.3 (3)	C24—C19—C20—C21	−0.8 (3)
C39—O7—C49—O8	2.6 (2)	C24—C19—C18—O3	−77.0 (2)
C39—O7—C49—C50	−176.88 (13)	C24—C23—C22—C21	−0.2 (3)
C13—C12—C11—O1	−176.45 (14)	C58—C57—C62—C61	0.5 (3)
C13—C12—C11—O2	4.6 (3)	C58—C57—C56—O9	108.43 (18)
C45—C42—C41—C40	168.67 (14)	C59—C60—C61—C62	−1.3 (3)
C45—C42—C43—C44	−179.26 (14)	C20—C19—C24—C23	0.2 (3)
C45—C42—C43—C48	0.6 (2)	C20—C19—C18—O3	103.2 (2)
C45—C46—C47—C48	−0.7 (3)	C20—C21—C22—C23	−0.4 (3)
C43—C42—C41—C40	−13.5 (2)	C18—O3—C15—C16	−5.2 (2)
C43—C42—C45—C46	−0.2 (2)	C18—O3—C15—C14	173.25 (16)
C43—C48—C47—C46	1.1 (3)	C18—C19—C24—C23	−179.55 (17)
C4—C5—C6—C1	−16.7 (2)	C18—C19—C20—C21	178.91 (17)
C4—C5—C10—C9	0.5 (3)	C32—O6—C29—C30	−177.81 (16)
C4—C3—C2—O4	−71.61 (18)	C32—O6—C29—C28	1.8 (3)
C4—C3—C2—C1	46.18 (19)	C32—C33—C34—C35	−175.7 (2)
C4—C7—C8—C9	0.8 (3)	C32—C33—C38—C37	176.56 (19)
C3—C4—C7—C8	178.08 (16)	C34—C33—C32—O6	−127.81 (19)
C19—C24—C23—C22	0.3 (3)	C34—C33—C38—C37	−0.3 (3)
C19—C20—C21—C22	0.9 (3)	C38—C33—C32—O6	55.4 (2)
C51—C50—C49—O7	−170.71 (14)	C38—C33—C34—C35	1.1 (3)
C51—C50—C49—O8	9.8 (3)	C72—C71—C70—O12	−135.41 (19)
C1—O1—C11—O2	0.1 (2)	C72—C71—C76—C75	−0.3 (3)
C1—O1—C11—C12	−178.79 (13)	C72—C73—C74—C75	−1.0 (4)
C30—C29—C28—C27	−0.5 (3)	C37—C36—C35—C34	−0.9 (3)
C69—C64—C63—O10	−12.0 (2)	C70—O12—C67—C68	−178.67 (17)
C69—C64—C63—O11	167.45 (18)	C70—O12—C67—C66	−0.3 (3)
C69—C64—C65—C66	0.1 (3)	C70—C71—C72—C73	−176.6 (2)
C69—C68—C67—O12	178.38 (16)	C70—C71—C76—C75	176.4 (2)
C69—C68—C67—C66	−0.1 (3)	C35—C36—C37—C38	1.8 (3)
C26—C27—C28—C29	0.3 (3)	C76—C71—C72—C73	0.2 (3)
C62—C57—C56—O9	−73.3 (2)	C76—C71—C70—O12	47.9 (3)
C62—C57—C58—C59	−0.9 (3)	C73—C74—C75—C76	0.9 (4)

(2R,3S)-1,2,3,4-Tetrahydronaphthalene-2,3-diyl bis(4-methoxybenzoate) (8)

Crystal data

C26H24O6	F(000) = 912
Mr = 432.45	Dx = 1.335 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 9.033 (3) Å	Cell parameters from 4943 reflections
b = 6.427 (2) Å	θ = 3.2–27.5°
c = 37.080 (14) Å	µ = 0.10 mm^−1
β = 91.948 (7)°	T = 193 K
V = 2151.4 (14) Å^3	Prism, colourless
Z = 4	0.24 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	4213 reflections with I > 2σ(I)
dtprofit.ref scans	Rint = 0.055
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	θmax = 27.5°, θmin = 3.4°
Tmin = 0.893, Tmax = 1.000	h = −11→11
20997 measured reflections	k = −8→8
4916 independent reflections	l = −46→48

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0577P)^2 + 0.2076P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4916 reflections	Δρmax = 0.20 e Å^−3
291 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O4	−0.35154 (8)	−0.42717 (12)	−0.58411 (2)	0.0334 (2)
O1	−0.43359 (9)	−0.41852 (13)	−0.65657 (2)	0.0355 (2)
O6	−0.87435 (10)	−0.25409 (13)	−0.47963 (2)	0.0396 (2)
O2	−0.37639 (10)	−0.71494 (14)	−0.68506 (3)	0.0437 (2)
O3	−1.06172 (10)	−0.57749 (17)	−0.72574 (3)	0.0490 (3)
O5	−0.46471 (11)	−0.73940 (14)	−0.58574 (3)	0.0511 (3)
C23	−0.76839 (12)	−0.31463 (18)	−0.50262 (3)	0.0305 (2)
C21	−0.55206 (12)	−0.26755 (18)	−0.53743 (3)	0.0314 (2)
H21	−0.473892	−0.181427	−0.545233	0.038*
C4	−0.02174 (12)	−0.24833 (17)	−0.60870 (3)	0.0283 (2)
C20	−0.56363 (11)	−0.47017 (18)	−0.55002 (3)	0.0292 (2)
C22	−0.65296 (12)	−0.18891 (19)	−0.51362 (3)	0.0322 (3)
H22	−0.643396	−0.050410	−0.504898	0.039*
C11	−0.46608 (13)	−0.58583 (18)	−0.67733 (3)	0.0320 (3)
C5	−0.10024 (12)	−0.10886 (17)	−0.63082 (3)	0.0289 (2)
C17	−0.71936 (13)	−0.42217 (19)	−0.68137 (3)	0.0341 (3)
H17	−0.684389	−0.309222	−0.666912	0.041*
C1	−0.28013 (12)	−0.38695 (18)	−0.64551 (3)	0.0312 (2)
H1	−0.214919	−0.442561	−0.664524	0.037*
C2	−0.24525 (12)	−0.49787 (18)	−0.61014 (3)	0.0316 (2)
H2	−0.255637	−0.651483	−0.613700	0.038*
C25	−0.68081 (13)	−0.59369 (18)	−0.53909 (3)	0.0334 (3)
H25	−0.690507	−0.732139	−0.547836	0.040*
C7	0.12504 (13)	−0.20538 (19)	−0.59894 (3)	0.0340 (3)
H7	0.179121	−0.300670	−0.583993	0.041*
C12	−0.62324 (12)	−0.58378 (18)	−0.68972 (3)	0.0307 (2)
C24	−0.78284 (13)	−0.51638 (18)	−0.51567 (3)	0.0342 (3)
H24	−0.862836	−0.601075	−0.508487	0.041*
C16	−0.86451 (13)	−0.4252 (2)	−0.69392 (3)	0.0372 (3)
H16	−0.929370	−0.315037	−0.687967	0.045*
C19	−0.45783 (12)	−0.56214 (18)	−0.57505 (3)	0.0326 (3)
C3	−0.08953 (13)	−0.44838 (19)	−0.59578 (3)	0.0358 (3)
H3A	−0.091137	−0.443758	−0.569106	0.043*
H3B	−0.023784	−0.564625	−0.602348	0.043*
C10	−0.02973 (14)	0.06900 (19)	−0.64288 (3)	0.0360 (3)
H10	−0.082449	0.163325	−0.658299	0.043*
C6	−0.25825 (13)	−0.15433 (18)	−0.64222 (3)	0.0330 (3)
H6A	−0.282076	−0.086860	−0.665704	0.040*
H6B	−0.325647	−0.097433	−0.624166	0.040*
C15	−0.91618 (13)	−0.5884 (2)	−0.71518 (3)	0.0364 (3)
C8	0.19386 (13)	−0.0263 (2)	−0.61061 (3)	0.0396 (3)
H8	0.293782	0.001968	−0.603418	0.048*
C13	−0.67609 (14)	−0.7457 (2)	−0.71123 (3)	0.0373 (3)
H13	−0.611327	−0.855941	−0.717221	0.045*
C9	0.11616 (14)	0.1107 (2)	−0.63276 (4)	0.0413 (3)
H9	0.162704	0.233501	−0.641052	0.050*
C14	−0.82177 (14)	−0.7494 (2)	−0.72413 (3)	0.0400 (3)
H14	−0.856705	−0.860928	−0.738927	0.048*
C26	−0.85986 (16)	−0.0570 (2)	−0.46237 (4)	0.0465 (3)
H26A	−0.941190	−0.037839	−0.445851	0.070*
H26B	−0.863363	0.053378	−0.480614	0.070*
H26C	−0.765068	−0.050762	−0.448749	0.070*
C18	−1.12170 (16)	−0.7432 (3)	−0.74715 (5)	0.0628 (5)
H18A	−1.104362	−0.875685	−0.734611	0.094*
H18B	−1.073554	−0.746097	−0.770438	0.094*
H18C	−1.228428	−0.721964	−0.751144	0.094*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0326 (4)	0.0331 (4)	0.0350 (4)	−0.0042 (3)	0.0088 (3)	−0.0036 (3)
O1	0.0285 (4)	0.0392 (5)	0.0388 (4)	−0.0010 (3)	−0.0001 (3)	−0.0088 (4)
O6	0.0370 (5)	0.0392 (5)	0.0435 (5)	−0.0023 (4)	0.0136 (4)	−0.0027 (4)
O2	0.0350 (5)	0.0428 (5)	0.0531 (5)	0.0065 (4)	−0.0012 (4)	−0.0113 (4)
O3	0.0313 (5)	0.0688 (7)	0.0468 (5)	0.0020 (4)	−0.0022 (4)	−0.0112 (5)
O5	0.0466 (6)	0.0360 (5)	0.0722 (7)	−0.0096 (4)	0.0230 (5)	−0.0152 (5)
C23	0.0278 (5)	0.0350 (6)	0.0286 (5)	0.0010 (4)	0.0024 (4)	0.0031 (4)
C21	0.0268 (5)	0.0348 (6)	0.0326 (6)	−0.0067 (4)	0.0008 (4)	−0.0008 (5)
C4	0.0304 (5)	0.0313 (6)	0.0237 (5)	0.0016 (4)	0.0055 (4)	−0.0026 (4)
C20	0.0270 (5)	0.0317 (6)	0.0287 (5)	−0.0006 (4)	−0.0004 (4)	0.0015 (4)
C22	0.0314 (6)	0.0320 (6)	0.0334 (6)	−0.0047 (5)	0.0007 (4)	−0.0029 (5)
C11	0.0350 (6)	0.0327 (6)	0.0286 (5)	−0.0016 (5)	0.0032 (4)	0.0001 (4)
C5	0.0301 (5)	0.0305 (6)	0.0264 (5)	0.0015 (4)	0.0038 (4)	−0.0020 (4)
C17	0.0355 (6)	0.0349 (6)	0.0322 (6)	−0.0021 (5)	0.0055 (5)	−0.0036 (5)
C1	0.0259 (5)	0.0350 (6)	0.0327 (6)	−0.0013 (4)	0.0015 (4)	−0.0029 (5)
C2	0.0312 (6)	0.0294 (6)	0.0347 (6)	0.0000 (4)	0.0071 (4)	−0.0007 (5)
C25	0.0346 (6)	0.0274 (6)	0.0384 (6)	−0.0020 (4)	0.0024 (5)	0.0019 (5)
C7	0.0318 (6)	0.0402 (7)	0.0300 (6)	0.0024 (5)	0.0011 (4)	−0.0010 (5)
C12	0.0312 (6)	0.0347 (6)	0.0266 (5)	−0.0019 (4)	0.0040 (4)	−0.0013 (4)
C24	0.0320 (6)	0.0304 (6)	0.0405 (6)	−0.0055 (5)	0.0069 (5)	0.0067 (5)
C16	0.0343 (6)	0.0411 (7)	0.0365 (6)	0.0043 (5)	0.0069 (5)	−0.0028 (5)
C19	0.0297 (6)	0.0327 (6)	0.0355 (6)	−0.0032 (4)	0.0009 (4)	−0.0004 (5)
C3	0.0317 (6)	0.0358 (6)	0.0398 (6)	0.0020 (5)	0.0005 (5)	0.0081 (5)
C10	0.0402 (6)	0.0335 (6)	0.0345 (6)	−0.0004 (5)	0.0034 (5)	0.0032 (5)
C6	0.0315 (6)	0.0324 (6)	0.0348 (6)	0.0019 (5)	−0.0006 (4)	0.0031 (5)
C15	0.0303 (6)	0.0505 (7)	0.0285 (6)	−0.0020 (5)	0.0028 (4)	0.0003 (5)
C8	0.0307 (6)	0.0481 (7)	0.0402 (6)	−0.0069 (5)	0.0024 (5)	−0.0037 (6)
C13	0.0369 (6)	0.0391 (7)	0.0359 (6)	0.0022 (5)	0.0016 (5)	−0.0074 (5)
C9	0.0425 (7)	0.0389 (7)	0.0428 (7)	−0.0109 (5)	0.0062 (5)	0.0027 (5)
C14	0.0380 (6)	0.0472 (8)	0.0346 (6)	−0.0031 (5)	−0.0005 (5)	−0.0113 (5)
C26	0.0478 (8)	0.0444 (8)	0.0479 (7)	0.0013 (6)	0.0126 (6)	−0.0101 (6)
C18	0.0377 (7)	0.0893 (13)	0.0608 (9)	−0.0022 (8)	−0.0081 (7)	−0.0275 (9)

Geometric parameters (Å, º)

O4—C2	1.4570 (13)	C2—H2	1.0000
O4—C19	1.3450 (14)	C2—C3	1.5207 (16)
O1—C11	1.3488 (14)	C25—H25	0.9500
O1—C1	1.4465 (14)	C25—C24	1.3802 (16)
O6—C23	1.3601 (14)	C7—H7	0.9500
O6—C26	1.4233 (16)	C7—C8	1.3841 (18)
O2—C11	1.2012 (14)	C12—C13	1.3860 (16)
O3—C15	1.3607 (15)	C24—H24	0.9500
O3—C18	1.4246 (18)	C16—H16	0.9500
O5—C19	1.2071 (15)	C16—C15	1.3833 (18)
C23—C22	1.3912 (16)	C3—H3A	0.9900
C23—C24	1.3885 (17)	C3—H3B	0.9900
C21—H21	0.9500	C10—H10	0.9500
C21—C20	1.3860 (16)	C10—C9	1.3841 (18)
C21—C22	1.3857 (16)	C6—H6A	0.9900
C4—C5	1.3928 (16)	C6—H6B	0.9900
C4—C7	1.3901 (16)	C15—C14	1.3885 (18)
C4—C3	1.5091 (17)	C8—H8	0.9500
C20—C25	1.3943 (16)	C8—C9	1.3800 (19)
C20—C19	1.4780 (16)	C13—H13	0.9500
C22—H22	0.9500	C13—C14	1.3850 (18)
C11—C12	1.4772 (16)	C9—H9	0.9500
C5—C10	1.3898 (17)	C14—H14	0.9500
C5—C6	1.5033 (16)	C26—H26A	0.9800
C17—H17	0.9500	C26—H26B	0.9800
C17—C12	1.3953 (17)	C26—H26C	0.9800
C17—C16	1.3764 (17)	C18—H18A	0.9800
C1—H1	1.0000	C18—H18B	0.9800
C1—C2	1.5163 (17)	C18—H18C	0.9800
C1—C6	1.5124 (17)
C19—O4—C2	117.16 (9)	C25—C24—C23	119.91 (10)
C11—O1—C1	117.48 (9)	C25—C24—H24	120.0
C23—O6—C26	118.73 (10)	C17—C16—H16	119.9
C15—O3—C18	117.86 (11)	C17—C16—C15	120.18 (11)
O6—C23—C22	124.62 (11)	C15—C16—H16	119.9
O6—C23—C24	115.20 (10)	O4—C19—C20	112.41 (10)
C24—C23—C22	120.17 (11)	O5—C19—O4	123.77 (11)
C20—C21—H21	119.6	O5—C19—C20	123.81 (11)
C22—C21—H21	119.6	C4—C3—C2	116.58 (10)
C22—C21—C20	120.90 (10)	C4—C3—H3A	108.1
C5—C4—C3	122.09 (10)	C4—C3—H3B	108.1
C7—C4—C5	119.18 (10)	C2—C3—H3A	108.1
C7—C4—C3	118.71 (10)	C2—C3—H3B	108.1
C21—C20—C25	119.10 (10)	H3A—C3—H3B	107.3
C21—C20—C19	122.97 (10)	C5—C10—H10	119.5
C25—C20—C19	117.92 (10)	C9—C10—C5	120.98 (12)
C23—C22—H22	120.3	C9—C10—H10	119.5
C21—C22—C23	119.39 (11)	C5—C6—C1	109.57 (9)
C21—C22—H22	120.3	C5—C6—H6A	109.8
O1—C11—C12	111.01 (10)	C5—C6—H6B	109.8
O2—C11—O1	123.46 (11)	C1—C6—H6A	109.8
O2—C11—C12	125.51 (11)	C1—C6—H6B	109.8
C4—C5—C6	120.00 (10)	H6A—C6—H6B	108.2
C10—C5—C4	119.28 (11)	O3—C15—C16	115.41 (11)
C10—C5—C6	120.70 (10)	O3—C15—C14	124.39 (11)
C12—C17—H17	119.8	C16—C15—C14	120.19 (11)
C16—C17—H17	119.8	C7—C8—H8	120.3
C16—C17—C12	120.47 (11)	C9—C8—C7	119.47 (12)
O1—C1—H1	109.4	C9—C8—H8	120.3
O1—C1—C2	110.38 (9)	C12—C13—H13	119.5
O1—C1—C6	106.43 (9)	C14—C13—C12	121.09 (11)
C2—C1—H1	109.4	C14—C13—H13	119.5
C6—C1—H1	109.4	C10—C9—H9	120.1
C6—C1—C2	111.85 (10)	C8—C9—C10	119.87 (12)
O4—C2—C1	107.71 (9)	C8—C9—H9	120.1
O4—C2—H2	109.5	C15—C14—H14	120.4
O4—C2—C3	108.98 (10)	C13—C14—C15	119.26 (11)
C1—C2—H2	109.5	C13—C14—H14	120.4
C1—C2—C3	111.54 (9)	O6—C26—H26A	109.5
C3—C2—H2	109.5	O6—C26—H26B	109.5
C20—C25—H25	119.7	O6—C26—H26C	109.5
C24—C25—C20	120.51 (11)	H26A—C26—H26B	109.5
C24—C25—H25	119.7	H26A—C26—H26C	109.5
C4—C7—H7	119.4	H26B—C26—H26C	109.5
C8—C7—C4	121.22 (11)	O3—C18—H18A	109.5
C8—C7—H7	119.4	O3—C18—H18B	109.5
C17—C12—C11	122.44 (11)	O3—C18—H18C	109.5
C13—C12—C11	118.74 (10)	H18A—C18—H18B	109.5
C13—C12—C17	118.80 (11)	H18A—C18—H18C	109.5
C23—C24—H24	120.0	H18B—C18—H18C	109.5
O4—C2—C3—C4	−95.62 (12)	C1—O1—C11—C12	−173.61 (9)
O1—C11—C12—C17	2.17 (15)	C1—C2—C3—C4	23.17 (14)
O1—C11—C12—C13	−179.58 (10)	C2—O4—C19—O5	4.04 (17)
O1—C1—C2—O4	−54.30 (12)	C2—O4—C19—C20	−176.99 (9)
O1—C1—C2—C3	−173.84 (9)	C2—C1—C6—C5	59.51 (12)
O1—C1—C6—C5	−179.86 (8)	C25—C20—C19—O4	178.88 (10)
O6—C23—C22—C21	−179.50 (10)	C25—C20—C19—O5	−2.15 (18)
O6—C23—C24—C25	−179.75 (10)	C7—C4—C5—C10	0.54 (16)
O2—C11—C12—C17	−176.18 (12)	C7—C4—C5—C6	178.92 (10)
O2—C11—C12—C13	2.08 (18)	C7—C4—C3—C2	−174.26 (10)
O3—C15—C14—C13	−178.78 (11)	C7—C8—C9—C10	0.48 (19)
C21—C20—C25—C24	−0.88 (17)	C12—C17—C16—C15	−0.43 (18)
C21—C20—C19—O4	−0.39 (16)	C12—C13—C14—C15	−0.24 (19)
C21—C20—C19—O5	178.58 (12)	C24—C23—C22—C21	−0.57 (17)
C4—C5—C10—C9	−1.02 (17)	C16—C17—C12—C11	179.07 (10)
C4—C5—C6—C1	−31.79 (14)	C16—C17—C12—C13	0.82 (17)
C4—C7—C8—C9	−0.96 (18)	C16—C15—C14—C13	0.64 (19)
C20—C21—C22—C23	−0.82 (17)	C19—O4—C2—C1	107.25 (11)
C20—C25—C24—C23	−0.49 (18)	C19—O4—C2—C3	−131.59 (10)
C22—C23—C24—C25	1.22 (17)	C19—C20—C25—C24	179.82 (10)
C22—C21—C20—C25	1.54 (17)	C3—C4—C5—C10	−177.65 (10)
C22—C21—C20—C19	−179.20 (10)	C3—C4—C5—C6	0.73 (16)
C11—O1—C1—C2	−89.50 (12)	C3—C4—C7—C8	178.69 (11)
C11—O1—C1—C6	148.93 (10)	C10—C5—C6—C1	146.56 (11)
C11—C12—C13—C14	−178.80 (11)	C6—C5—C10—C9	−179.39 (11)
C5—C4—C7—C8	0.45 (17)	C6—C1—C2—O4	64.00 (12)
C5—C4—C3—C2	3.93 (16)	C6—C1—C2—C3	−55.54 (13)
C5—C10—C9—C8	0.51 (19)	C26—O6—C23—C22	−6.92 (17)
C17—C12—C13—C14	−0.48 (18)	C26—O6—C23—C24	174.11 (11)
C17—C16—C15—O3	179.16 (11)	C18—O3—C15—C16	−178.89 (13)
C17—C16—C15—C14	−0.31 (19)	C18—O3—C15—C14	0.55 (19)
C1—O1—C11—O2	4.77 (16)

(2R,3S)-1,2,3,4-Tetrahydronaphthalene-2,3-diyl bis(2,4,6-trifluorobenzoate) (9)

Crystal data

C24H14F6O4	F(000) = 1952
Mr = 480.35	Dx = 1.526 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71075 Å
a = 23.308 (10) Å	Cell parameters from 4856 reflections
b = 7.132 (3) Å	θ = 3.0–27.5°
c = 27.253 (9) Å	µ = 0.14 mm^−1
β = 112.62 (3)°	T = 193 K
V = 4182 (3) Å^3	Prism, colorless
Z = 8	0.24 × 0.12 × 0.09 mm

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	3880 reflections with I > 2σ(I)
dtprofit.ref scans	Rint = 0.044
Absorption correction: empirical (using intensity measurements) DTABSCOR	θmax = 27.5°, θmin = 3.0°
Tmin = 0.797, Tmax = 1.000	h = −30→28
20765 measured reflections	k = −9→9
4763 independent reflections	l = −35→35

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0582P)^2 + 0.5393P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
4763 reflections	Δρmax = 0.22 e Å^−3
307 parameters	Δρmin = −0.22 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
F6	−0.59538 (4)	−0.86340 (12)	−0.25229 (4)	0.0460 (3)
F3	−0.69961 (5)	−0.65624 (13)	−0.39473 (4)	0.0569 (3)
F5	−0.73657 (5)	−1.00892 (14)	−0.17474 (4)	0.0561 (3)
O1	−0.65445 (5)	−0.32340 (14)	−0.37865 (4)	0.0348 (3)
O3	−0.59720 (5)	−0.51045 (15)	−0.28090 (4)	0.0389 (3)
F4	−0.67906 (6)	−0.38595 (14)	−0.18057 (5)	0.0658 (3)
O4	−0.58017 (6)	−0.32647 (15)	−0.20972 (5)	0.0471 (3)
F2	−0.89314 (5)	−0.74404 (17)	−0.53019 (5)	0.0710 (4)
O2	−0.72512 (5)	−0.10141 (16)	−0.38462 (5)	0.0530 (3)
F1	−0.82341 (6)	−0.13833 (14)	−0.47905 (6)	0.0881 (5)
C18	−0.60116 (7)	−0.4672 (2)	−0.23445 (6)	0.0335 (3)
C11	−0.71193 (7)	−0.2528 (2)	−0.39675 (6)	0.0338 (3)
C19	−0.63521 (7)	−0.6143 (2)	−0.21784 (6)	0.0324 (3)
C12	−0.75773 (7)	−0.3858 (2)	−0.43369 (6)	0.0327 (3)
C2	−0.56396 (7)	−0.3810 (2)	−0.30194 (6)	0.0336 (3)
H2	−0.528538	−0.323624	−0.271892	0.040*
C4	−0.51410 (7)	−0.3798 (2)	−0.36877 (6)	0.0347 (3)
C24	−0.63288 (7)	−0.8053 (2)	−0.22798 (6)	0.0334 (3)
C1	−0.60687 (7)	−0.2275 (2)	−0.33442 (6)	0.0338 (3)
H1	−0.626082	−0.159152	−0.312525	0.041*
C3	−0.53896 (7)	−0.4985 (2)	−0.33558 (6)	0.0358 (3)
H3A	−0.505325	−0.580416	−0.312073	0.043*
H3B	−0.572576	−0.580005	−0.359305	0.043*
C5	−0.52963 (7)	−0.1900 (2)	−0.37866 (6)	0.0366 (4)
C17	−0.75112 (7)	−0.5797 (2)	−0.43076 (6)	0.0371 (4)
C6	−0.57057 (7)	−0.0928 (2)	−0.35479 (7)	0.0388 (4)
H6A	−0.600234	−0.010341	−0.382039	0.047*
H6B	−0.544278	−0.012360	−0.325027	0.047*
C20	−0.67321 (8)	−0.5675 (2)	−0.19076 (6)	0.0396 (4)
C22	−0.70268 (7)	−0.8798 (2)	−0.18804 (6)	0.0389 (4)
C23	−0.66541 (7)	−0.9399 (2)	−0.21340 (6)	0.0387 (4)
H23	−0.662217	−1.069007	−0.220563	0.046*
C21	−0.70778 (8)	−0.6952 (2)	−0.17581 (7)	0.0416 (4)
H21	−0.733785	−0.657632	−0.157963	0.050*
C13	−0.81366 (8)	−0.3227 (2)	−0.47204 (7)	0.0443 (4)
C7	−0.47607 (8)	−0.4632 (3)	−0.39167 (7)	0.0452 (4)
H7	−0.465397	−0.591903	−0.385128	0.054*
C15	−0.84887 (8)	−0.6264 (2)	−0.49860 (7)	0.0456 (4)
C16	−0.79580 (8)	−0.7021 (2)	−0.46219 (7)	0.0478 (4)
H16	−0.789935	−0.834012	−0.458670	0.057*
C10	−0.50651 (8)	−0.0892 (3)	−0.41096 (7)	0.0482 (4)
H10	−0.516759	0.039693	−0.417708	0.058*
C14	−0.85954 (8)	−0.4386 (3)	−0.50494 (7)	0.0478 (4)
H14	−0.896844	−0.389864	−0.530823	0.057*
C9	−0.46904 (9)	−0.1735 (3)	−0.43327 (8)	0.0611 (5)
H9	−0.453709	−0.102928	−0.455201	0.073*
C8	−0.45384 (9)	−0.3613 (3)	−0.42362 (8)	0.0586 (5)
H8	−0.428125	−0.419917	−0.438983	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F6	0.0531 (6)	0.0338 (5)	0.0632 (6)	0.0034 (4)	0.0359 (5)	−0.0036 (4)
F3	0.0447 (6)	0.0292 (5)	0.0765 (8)	0.0044 (4)	0.0009 (5)	0.0005 (5)
F5	0.0688 (7)	0.0420 (6)	0.0721 (7)	−0.0054 (5)	0.0432 (6)	0.0102 (5)
O1	0.0293 (5)	0.0313 (5)	0.0402 (6)	0.0000 (4)	0.0093 (5)	−0.0086 (4)
O3	0.0455 (6)	0.0362 (6)	0.0383 (6)	−0.0110 (5)	0.0198 (5)	−0.0040 (5)
F4	0.1001 (9)	0.0298 (5)	0.0994 (9)	0.0034 (5)	0.0737 (8)	−0.0053 (5)
O4	0.0595 (7)	0.0358 (6)	0.0512 (7)	−0.0139 (5)	0.0272 (6)	−0.0120 (5)
F2	0.0597 (7)	0.0657 (8)	0.0698 (8)	−0.0273 (6)	0.0052 (6)	−0.0206 (6)
O2	0.0416 (7)	0.0333 (6)	0.0747 (9)	0.0055 (5)	0.0119 (6)	−0.0136 (6)
F1	0.0651 (8)	0.0339 (6)	0.1146 (11)	−0.0013 (5)	−0.0214 (7)	0.0194 (6)
C18	0.0327 (8)	0.0299 (7)	0.0373 (8)	0.0005 (6)	0.0128 (6)	−0.0017 (6)
C11	0.0336 (8)	0.0267 (7)	0.0412 (9)	0.0004 (6)	0.0147 (7)	0.0010 (6)
C19	0.0324 (7)	0.0293 (7)	0.0348 (8)	0.0006 (6)	0.0120 (6)	0.0008 (6)
C12	0.0330 (7)	0.0299 (7)	0.0359 (8)	−0.0033 (6)	0.0139 (6)	0.0009 (6)
C2	0.0333 (8)	0.0311 (7)	0.0357 (8)	−0.0060 (6)	0.0125 (7)	0.0000 (6)
C4	0.0294 (7)	0.0390 (8)	0.0325 (8)	0.0011 (6)	0.0081 (6)	0.0015 (6)
C24	0.0328 (8)	0.0328 (8)	0.0360 (8)	0.0032 (6)	0.0148 (7)	−0.0016 (6)
C1	0.0322 (7)	0.0290 (7)	0.0384 (8)	−0.0035 (6)	0.0116 (7)	−0.0091 (6)
C3	0.0354 (8)	0.0304 (8)	0.0410 (9)	0.0040 (6)	0.0142 (7)	0.0030 (6)
C5	0.0314 (8)	0.0374 (8)	0.0368 (9)	−0.0021 (6)	0.0083 (7)	0.0026 (6)
C17	0.0363 (8)	0.0326 (8)	0.0412 (9)	−0.0007 (6)	0.0137 (7)	−0.0016 (7)
C6	0.0378 (8)	0.0286 (7)	0.0473 (9)	−0.0023 (6)	0.0134 (7)	0.0000 (7)
C20	0.0496 (9)	0.0278 (8)	0.0458 (9)	0.0048 (6)	0.0233 (8)	0.0001 (7)
C22	0.0406 (9)	0.0359 (8)	0.0413 (9)	−0.0012 (7)	0.0168 (7)	0.0096 (7)
C23	0.0441 (9)	0.0285 (7)	0.0447 (9)	−0.0004 (6)	0.0183 (8)	0.0011 (7)
C21	0.0479 (9)	0.0385 (9)	0.0458 (10)	0.0064 (7)	0.0263 (8)	0.0055 (7)
C13	0.0411 (9)	0.0331 (8)	0.0516 (10)	−0.0039 (7)	0.0098 (8)	0.0086 (7)
C7	0.0405 (9)	0.0524 (10)	0.0435 (10)	0.0082 (7)	0.0170 (8)	0.0029 (8)
C15	0.0437 (10)	0.0490 (10)	0.0420 (10)	−0.0177 (8)	0.0141 (8)	−0.0101 (8)
C16	0.0491 (10)	0.0339 (8)	0.0573 (11)	−0.0072 (7)	0.0169 (9)	−0.0100 (8)
C10	0.0423 (9)	0.0509 (10)	0.0487 (10)	−0.0010 (8)	0.0145 (8)	0.0139 (8)
C14	0.0395 (9)	0.0525 (10)	0.0425 (10)	−0.0087 (8)	0.0061 (8)	0.0059 (8)
C9	0.0546 (11)	0.0807 (15)	0.0554 (12)	0.0017 (10)	0.0294 (10)	0.0209 (11)
C8	0.0496 (11)	0.0809 (15)	0.0537 (12)	0.0099 (10)	0.0294 (10)	0.0084 (10)

Geometric parameters (Å, º)

F6—C24	1.3492 (17)	C1—C6	1.519 (2)
F3—C17	1.3404 (19)	C3—H3A	0.9900
F5—C22	1.3508 (18)	C3—H3B	0.9900
O1—C11	1.3356 (19)	C5—C6	1.514 (2)
O1—C1	1.4567 (18)	C5—C10	1.395 (2)
O3—C18	1.3401 (19)	C17—C16	1.376 (2)
O3—C2	1.4569 (17)	C6—H6A	0.9900
F4—C20	1.3422 (18)	C6—H6B	0.9900
O4—C18	1.2032 (18)	C20—C21	1.377 (2)
F2—C15	1.3514 (19)	C22—C23	1.370 (2)
O2—C11	1.2033 (18)	C22—C21	1.374 (2)
F1—C13	1.3359 (19)	C23—H23	0.9500
C18—C19	1.487 (2)	C21—H21	0.9500
C11—C12	1.492 (2)	C13—C14	1.376 (2)
C19—C24	1.395 (2)	C7—H7	0.9500
C19—C20	1.394 (2)	C7—C8	1.379 (3)
C12—C17	1.391 (2)	C15—C16	1.365 (3)
C12—C13	1.395 (2)	C15—C14	1.361 (3)
C2—H2	1.0000	C16—H16	0.9500
C2—C1	1.517 (2)	C10—H10	0.9500
C2—C3	1.514 (2)	C10—C9	1.379 (3)
C4—C3	1.508 (2)	C14—H14	0.9500
C4—C5	1.400 (2)	C9—H9	0.9500
C4—C7	1.398 (2)	C9—C8	1.385 (3)
C24—C23	1.374 (2)	C8—H8	0.9500
C1—H1	1.0000
C11—O1—C1	117.70 (11)	C16—C17—C12	123.69 (15)
C18—O3—C2	117.80 (11)	C1—C6—H6A	108.9
O3—C18—C19	111.34 (12)	C1—C6—H6B	108.9
O4—C18—O3	124.07 (14)	C5—C6—C1	113.52 (13)
O4—C18—C19	124.59 (14)	C5—C6—H6A	108.9
O1—C11—C12	111.43 (12)	C5—C6—H6B	108.9
O2—C11—O1	124.25 (14)	H6A—C6—H6B	107.7
O2—C11—C12	124.32 (14)	F4—C20—C19	118.46 (14)
C24—C19—C18	124.24 (13)	F4—C20—C21	117.33 (14)
C20—C19—C18	120.94 (13)	C21—C20—C19	124.14 (15)
C20—C19—C24	114.82 (14)	F5—C22—C23	118.13 (14)
C17—C12—C11	123.98 (14)	F5—C22—C21	118.30 (14)
C17—C12—C13	114.49 (14)	C23—C22—C21	123.57 (15)
C13—C12—C11	121.37 (14)	C24—C23—H23	121.5
O3—C2—H2	109.5	C22—C23—C24	117.04 (14)
O3—C2—C1	110.85 (12)	C22—C23—H23	121.5
O3—C2—C3	105.94 (11)	C20—C21—H21	121.7
C1—C2—H2	109.5	C22—C21—C20	116.52 (15)
C3—C2—H2	109.5	C22—C21—H21	121.7
C3—C2—C1	111.52 (12)	F1—C13—C12	118.88 (14)
C5—C4—C3	121.86 (14)	F1—C13—C14	116.82 (15)
C7—C4—C3	118.99 (14)	C14—C13—C12	124.26 (16)
C7—C4—C5	119.12 (15)	C4—C7—H7	119.5
F6—C24—C19	118.62 (13)	C8—C7—C4	120.96 (17)
F6—C24—C23	117.48 (13)	C8—C7—H7	119.5
C23—C24—C19	123.87 (14)	F2—C15—C16	118.30 (16)
O1—C1—C2	105.38 (11)	F2—C15—C14	118.20 (16)
O1—C1—H1	110.5	C14—C15—C16	123.50 (16)
O1—C1—C6	110.38 (12)	C17—C16—H16	121.3
C2—C1—H1	110.5	C15—C16—C17	117.31 (16)
C2—C1—C6	109.57 (12)	C15—C16—H16	121.3
C6—C1—H1	110.5	C5—C10—H10	119.4
C2—C3—H3A	109.2	C9—C10—C5	121.16 (18)
C2—C3—H3B	109.2	C9—C10—H10	119.4
C4—C3—C2	112.25 (12)	C13—C14—H14	121.6
C4—C3—H3A	109.2	C15—C14—C13	116.74 (16)
C4—C3—H3B	109.2	C15—C14—H14	121.6
H3A—C3—H3B	107.9	C10—C9—H9	120.1
C4—C5—C6	121.25 (14)	C10—C9—C8	119.80 (17)
C10—C5—C4	119.04 (15)	C8—C9—H9	120.1
C10—C5—C6	119.72 (15)	C7—C8—C9	119.93 (18)
F3—C17—C12	119.68 (13)	C7—C8—H8	120.0
F3—C17—C16	116.60 (14)	C9—C8—H8	120.0
F6—C24—C23—C22	179.08 (14)	C2—O3—C18—O4	1.7 (2)
F3—C17—C16—C15	179.17 (15)	C2—O3—C18—C19	−178.84 (12)
F5—C22—C23—C24	178.04 (14)	C2—C1—C6—C5	46.35 (17)
F5—C22—C21—C20	−179.03 (15)	C4—C5—C6—C1	−17.0 (2)
O1—C11—C12—C17	29.2 (2)	C4—C5—C10—C9	0.2 (3)
O1—C11—C12—C13	−155.60 (15)	C4—C7—C8—C9	0.2 (3)
O1—C1—C6—C5	−69.26 (16)	C24—C19—C20—F4	−178.49 (14)
O3—C18—C19—C24	34.0 (2)	C24—C19—C20—C21	−1.7 (2)
O3—C18—C19—C20	−145.29 (14)	C1—O1—C11—O2	11.7 (2)
O3—C2—C1—O1	−62.45 (15)	C1—O1—C11—C12	−168.05 (12)
O3—C2—C1—C6	178.80 (11)	C1—C2—C3—C4	48.10 (16)
O3—C2—C3—C4	168.80 (11)	C3—C2—C1—O1	55.33 (15)
F4—C20—C21—C22	178.04 (15)	C3—C2—C1—C6	−63.42 (15)
O4—C18—C19—C24	−146.54 (16)	C3—C4—C5—C6	2.1 (2)
O4—C18—C19—C20	34.2 (2)	C3—C4—C5—C10	−178.16 (14)
F2—C15—C16—C17	179.43 (15)	C3—C4—C7—C8	178.03 (16)
F2—C15—C14—C13	179.77 (16)	C5—C4—C3—C2	−17.6 (2)
O2—C11—C12—C17	−150.50 (17)	C5—C4—C7—C8	0.0 (2)
O2—C11—C12—C13	24.7 (2)	C5—C10—C9—C8	0.0 (3)
F1—C13—C14—C15	178.46 (17)	C17—C12—C13—F1	−177.79 (16)
C18—O3—C2—C1	−86.51 (15)	C17—C12—C13—C14	0.0 (3)
C18—O3—C2—C3	152.36 (12)	C6—C5—C10—C9	179.94 (16)
C18—C19—C24—F6	3.1 (2)	C20—C19—C24—F6	−177.58 (13)
C18—C19—C24—C23	−178.71 (15)	C20—C19—C24—C23	0.6 (2)
C18—C19—C20—F4	0.8 (2)	C23—C22—C21—C20	0.5 (3)
C18—C19—C20—C21	177.64 (15)	C21—C22—C23—C24	−1.5 (2)
C11—O1—C1—C2	145.89 (13)	C13—C12—C17—F3	−178.94 (14)
C11—O1—C1—C6	−95.90 (15)	C13—C12—C17—C16	−0.9 (2)
C11—C12—C17—F3	−3.5 (2)	C7—C4—C3—C2	164.44 (14)
C11—C12—C17—C16	174.61 (15)	C7—C4—C5—C6	−179.92 (14)
C11—C12—C13—F1	6.6 (2)	C7—C4—C5—C10	−0.2 (2)
C11—C12—C13—C14	−175.62 (16)	C16—C15—C14—C13	−0.5 (3)
C19—C24—C23—C22	0.9 (2)	C10—C5—C6—C1	163.33 (14)
C19—C20—C21—C22	1.2 (3)	C10—C9—C8—C7	−0.1 (3)
C12—C17—C16—C15	1.0 (3)	C14—C15—C16—C17	−0.3 (3)
C12—C13—C14—C15	0.6 (3)