Unique hydrogen bonding in the acetone-mediated helical structure of (R,R)-3,3′-bisBINOL

The asymmetric unit of the title compound, C₄₀H₂₆O₄·-2(CH₃)₂CO, consists of one mol­ecule of (R,R)-3,3′-bisBINOL [(R,R)-1,1′:3′,3′′:1′′,1′′′-quater-2-naphthol] and two acetone mol­ecules. The central feature of the structure is the pair of unique sets of O—H...O...H—O hydrogen-bond arrangements between the two hydroxy groups of (R,R)-3,3′-bisBINOL and the O atom of acetone, which fixes the axial chirality of the 3,3′-bond as S, thus maintaining the helical structure of the bisBINOL in the M form.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.100
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               4540
           Count of symmetry unique reflns         4572
           Completeness (_total/calc)             99.30%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C40H26O4·2C3H6O	F(000) = 1448
Mr = 686.76	Dx = 1.268 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 38232 reflections
a = 13.403 (2) Å	θ = 3.0–27.5°
b = 15.5692 (10) Å	µ = 0.08 mm^−1
c = 17.235 (2) Å	T = 93 K
V = 3596.5 (7) Å^3	Block, colorless
Z = 4	0.60 × 0.55 × 0.50 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4366 reflections with I > 2σ(I)
ω scans	Rint = 0.050
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	θmax = 27.5°, θmin = 3.0°
Tmin = 0.952, Tmax = 0.968	h = −17→17
31216 measured reflections	k = −20→20
4540 independent reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 1.2636P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.100	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.21 e Å^−3
4540 reflections	Δρmin = −0.19 e Å^−3
489 parameters

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	−0.08777 (13)	0.01546 (11)	0.65147 (9)	0.0329 (3)
O2	0.06346 (12)	0.02066 (10)	0.81031 (10)	0.0298 (3)
O3	0.22721 (12)	0.10109 (10)	0.70258 (9)	0.0290 (3)
O4	0.39041 (12)	−0.05410 (10)	0.77821 (10)	0.0305 (3)
O5	0.04114 (12)	0.16047 (11)	0.63711 (9)	0.0329 (4)
O6	0.24774 (13)	−0.01320 (11)	0.89128 (9)	0.0332 (3)
C1	−0.14239 (15)	0.03622 (13)	0.78424 (12)	0.0245 (4)
C2	−0.14680 (16)	−0.00515 (14)	0.71339 (12)	0.0271 (4)
C3	−0.21574 (17)	−0.07256 (14)	0.70040 (14)	0.0316 (5)
H5	−0.2172	−0.1005	0.6514	0.038*
C4	−0.27996 (17)	−0.09787 (15)	0.75726 (14)	0.0319 (5)
H6	−0.3251	−0.1437	0.7476	0.038*
C5	−0.28040 (16)	−0.05662 (14)	0.83083 (13)	0.0285 (4)
C6	−0.34890 (17)	−0.07952 (16)	0.88987 (14)	0.0343 (5)
H7	−0.3951	−0.1247	0.8809	0.041*
C7	−0.34958 (18)	−0.03749 (16)	0.95971 (14)	0.0358 (5)
H8	−0.3966	−0.0527	0.9986	0.043*
C8	−0.27996 (17)	0.02841 (16)	0.97325 (14)	0.0329 (5)
H9	−0.2804	0.0576	1.0216	0.039*
C9	−0.21128 (17)	0.05136 (14)	0.91781 (13)	0.0283 (4)
H10	−0.1640	0.0951	0.9289	0.034*
C10	−0.21001 (15)	0.01047 (13)	0.84413 (13)	0.0254 (4)
C11	−0.07562 (15)	0.11183 (13)	0.79580 (12)	0.0243 (4)
C12	0.02620 (15)	0.10253 (13)	0.80782 (11)	0.0242 (4)
C13	0.08930 (15)	0.17577 (13)	0.81652 (11)	0.0237 (4)
C14	0.04616 (16)	0.25577 (13)	0.81826 (12)	0.0246 (4)
H11	0.0876	0.3044	0.8264	0.030*
C15	−0.05751 (15)	0.26864 (13)	0.80849 (12)	0.0248 (4)
C16	−0.09980 (16)	0.35216 (14)	0.81064 (13)	0.0288 (4)
H12	−0.0583	0.4006	0.8196	0.035*
C17	−0.20023 (17)	0.36328 (14)	0.79980 (13)	0.0307 (5)
H13	−0.2283	0.4192	0.8022	0.037*
C18	−0.26222 (17)	0.29157 (14)	0.78510 (14)	0.0307 (5)
H14	−0.3317	0.2999	0.7771	0.037*
C19	−0.22325 (16)	0.21018 (14)	0.78219 (13)	0.0285 (4)
H15	−0.2658	0.1629	0.7714	0.034*
C20	−0.11913 (15)	0.19570 (13)	0.79522 (12)	0.0243 (4)
C21	0.36725 (15)	0.12905 (13)	0.78190 (11)	0.0232 (4)
C22	0.26459 (15)	0.13343 (13)	0.77035 (12)	0.0238 (4)
C23	0.20017 (15)	0.17027 (13)	0.82767 (12)	0.0241 (4)
C24	0.24162 (16)	0.20631 (14)	0.89221 (12)	0.0259 (4)
H16	0.1990	0.2322	0.9295	0.031*
C25	0.34618 (16)	0.20657 (13)	0.90573 (12)	0.0251 (4)
C26	0.38821 (17)	0.24565 (15)	0.97228 (13)	0.0302 (5)
H17	0.3458	0.2714	1.0098	0.036*
C27	0.48981 (18)	0.24670 (17)	0.98319 (13)	0.0339 (5)
H18	0.5175	0.2747	1.0272	0.041*
C28	0.55301 (17)	0.20600 (16)	0.92873 (13)	0.0325 (5)
H19	0.6232	0.2068	0.9365	0.039*
C29	0.51451 (16)	0.16557 (15)	0.86516 (13)	0.0282 (4)
H20	0.5581	0.1367	0.8303	0.034*
C30	0.40980 (15)	0.16597 (13)	0.85027 (12)	0.0247 (4)
C31	0.43284 (15)	0.08421 (13)	0.72419 (12)	0.0247 (4)
C32	0.43858 (15)	−0.00399 (13)	0.72525 (12)	0.0256 (4)
C33	0.49733 (16)	−0.04926 (15)	0.67012 (13)	0.0292 (4)
H21	0.4966	−0.1103	0.6695	0.035*
C34	0.55447 (16)	−0.00578 (14)	0.61831 (13)	0.0296 (4)
H26	0.5929	−0.0368	0.5814	0.035*
C35	0.55761 (15)	0.08544 (14)	0.61846 (12)	0.0265 (4)
C36	0.62326 (17)	0.13222 (15)	0.56965 (13)	0.0311 (5)
H25	0.6656	0.1020	0.5349	0.037*
C37	0.62687 (18)	0.21972 (16)	0.57159 (14)	0.0329 (5)
H24	0.6714	0.2499	0.5385	0.039*
C38	0.56409 (17)	0.26531 (15)	0.62299 (13)	0.0304 (5)
H23	0.5666	0.3263	0.6244	0.036*
C39	0.49921 (16)	0.22195 (14)	0.67112 (13)	0.0278 (4)
H22	0.4567	0.2536	0.7047	0.033*
C40	0.49469 (15)	0.13120 (14)	0.67148 (12)	0.0243 (4)
C41	0.01214 (19)	0.23431 (16)	0.62296 (13)	0.0324 (5)
C42	−0.0909 (2)	0.25034 (19)	0.59392 (16)	0.0453 (6)
H29	−0.0879	0.2708	0.5402	0.068*
H28	−0.1232	0.2939	0.6264	0.068*
H27	−0.1294	0.1969	0.5961	0.068*
C43	0.0796 (2)	0.30987 (18)	0.63304 (15)	0.0488 (7)
H30	0.1436	0.2907	0.6543	0.073*
H31	0.0488	0.3511	0.6687	0.073*
H32	0.0907	0.3374	0.5827	0.073*
C44	0.26209 (19)	−0.00377 (17)	0.96072 (14)	0.0348 (5)
C45	0.3650 (2)	−0.0076 (2)	0.99450 (16)	0.0448 (6)
H33	0.4139	−0.0143	0.9526	0.067*
H34	0.3698	−0.0567	1.0300	0.067*
H35	0.3788	0.0455	1.0230	0.067*
C46	0.1773 (2)	0.0140 (3)	1.01510 (18)	0.0623 (9)
H36	0.1140	0.0096	0.9869	0.093*
H37	0.1843	0.0721	1.0364	0.093*
H38	0.1783	−0.0279	1.0575	0.093*
H1	−0.046 (2)	0.064 (2)	0.6598 (19)	0.052 (9)*
H2	0.128 (3)	0.019 (2)	0.832 (2)	0.071 (11)*
H3	0.164 (3)	0.125 (2)	0.691 (2)	0.070 (11)*
H4	0.347 (3)	−0.024 (2)	0.812 (2)	0.065 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0339 (8)	0.0367 (8)	0.0280 (7)	−0.0014 (7)	0.0000 (7)	−0.0038 (7)
O2	0.0236 (7)	0.0261 (7)	0.0396 (9)	0.0025 (6)	−0.0030 (7)	−0.0038 (6)
O3	0.0239 (7)	0.0385 (8)	0.0246 (7)	0.0019 (7)	−0.0026 (6)	−0.0086 (6)
O4	0.0288 (8)	0.0273 (7)	0.0354 (8)	−0.0021 (6)	0.0032 (7)	−0.0007 (7)
O5	0.0294 (8)	0.0415 (9)	0.0278 (7)	−0.0004 (7)	0.0005 (6)	−0.0013 (7)
O6	0.0310 (8)	0.0364 (8)	0.0321 (8)	−0.0003 (7)	0.0003 (7)	0.0029 (7)
C1	0.0201 (9)	0.0258 (9)	0.0275 (10)	0.0022 (8)	−0.0023 (8)	−0.0003 (8)
C2	0.0236 (9)	0.0304 (10)	0.0273 (10)	0.0046 (8)	−0.0039 (8)	0.0006 (8)
C3	0.0292 (10)	0.0319 (11)	0.0338 (11)	0.0035 (9)	−0.0080 (9)	−0.0048 (9)
C4	0.0256 (10)	0.0305 (11)	0.0397 (12)	−0.0029 (9)	−0.0082 (9)	−0.0018 (9)
C5	0.0205 (9)	0.0298 (10)	0.0352 (11)	0.0011 (8)	−0.0042 (8)	0.0002 (9)
C6	0.0238 (10)	0.0377 (12)	0.0413 (12)	−0.0041 (9)	−0.0034 (10)	0.0052 (10)
C7	0.0260 (11)	0.0435 (13)	0.0378 (12)	0.0032 (10)	0.0032 (10)	0.0117 (10)
C8	0.0302 (11)	0.0369 (12)	0.0316 (11)	0.0049 (10)	−0.0015 (9)	0.0009 (9)
C9	0.0265 (10)	0.0279 (10)	0.0306 (10)	0.0012 (9)	−0.0018 (9)	0.0002 (8)
C10	0.0195 (9)	0.0253 (9)	0.0314 (10)	0.0023 (8)	−0.0030 (8)	0.0004 (8)
C11	0.0223 (9)	0.0285 (10)	0.0222 (9)	0.0016 (8)	−0.0014 (8)	−0.0018 (8)
C12	0.0250 (10)	0.0268 (10)	0.0209 (9)	0.0018 (8)	0.0000 (8)	−0.0019 (8)
C13	0.0203 (9)	0.0305 (10)	0.0201 (8)	0.0003 (8)	−0.0005 (7)	−0.0030 (8)
C14	0.0219 (9)	0.0282 (10)	0.0238 (9)	−0.0027 (8)	−0.0002 (8)	−0.0006 (8)
C15	0.0211 (9)	0.0292 (10)	0.0242 (9)	−0.0004 (8)	−0.0004 (8)	0.0019 (8)
C16	0.0274 (10)	0.0271 (10)	0.0318 (10)	0.0009 (9)	−0.0021 (9)	0.0014 (8)
C17	0.0291 (11)	0.0282 (10)	0.0348 (11)	0.0036 (9)	−0.0028 (9)	0.0025 (9)
C18	0.0229 (10)	0.0329 (11)	0.0363 (11)	0.0027 (9)	−0.0012 (9)	0.0025 (9)
C19	0.0207 (10)	0.0293 (10)	0.0354 (11)	0.0004 (8)	−0.0023 (9)	0.0015 (9)
C20	0.0233 (10)	0.0281 (10)	0.0216 (9)	−0.0012 (8)	−0.0011 (8)	−0.0001 (8)
C21	0.0213 (9)	0.0252 (9)	0.0232 (9)	0.0004 (8)	−0.0002 (8)	−0.0001 (8)
C22	0.0229 (9)	0.0262 (9)	0.0223 (9)	−0.0005 (8)	−0.0020 (8)	−0.0008 (8)
C23	0.0201 (9)	0.0259 (9)	0.0265 (9)	0.0012 (8)	0.0009 (8)	0.0006 (8)
C24	0.0232 (10)	0.0285 (10)	0.0262 (10)	0.0016 (8)	0.0017 (8)	−0.0029 (8)
C25	0.0232 (10)	0.0270 (9)	0.0251 (9)	−0.0011 (8)	−0.0014 (8)	−0.0027 (8)
C26	0.0269 (11)	0.0351 (11)	0.0286 (10)	0.0007 (9)	0.0010 (9)	−0.0047 (9)
C27	0.0298 (11)	0.0428 (13)	0.0293 (11)	−0.0044 (10)	−0.0058 (9)	−0.0056 (10)
C28	0.0235 (10)	0.0431 (12)	0.0310 (11)	−0.0007 (10)	−0.0042 (9)	0.0004 (10)
C29	0.0220 (10)	0.0341 (11)	0.0284 (10)	0.0029 (8)	−0.0005 (8)	−0.0015 (9)
C30	0.0222 (9)	0.0277 (10)	0.0242 (9)	0.0004 (8)	−0.0014 (8)	0.0014 (8)
C31	0.0195 (9)	0.0280 (9)	0.0265 (9)	0.0023 (8)	−0.0028 (8)	−0.0042 (8)
C32	0.0200 (9)	0.0280 (10)	0.0287 (10)	0.0009 (8)	−0.0013 (8)	−0.0011 (8)
C33	0.0250 (10)	0.0276 (10)	0.0352 (11)	0.0052 (8)	−0.0015 (9)	−0.0034 (9)
C34	0.0234 (10)	0.0325 (11)	0.0328 (10)	0.0064 (9)	−0.0003 (9)	−0.0062 (9)
C35	0.0210 (9)	0.0324 (10)	0.0261 (9)	0.0039 (8)	−0.0013 (8)	−0.0042 (8)
C36	0.0258 (10)	0.0404 (12)	0.0270 (10)	0.0067 (10)	0.0036 (9)	−0.0030 (9)
C37	0.0272 (11)	0.0396 (12)	0.0319 (11)	−0.0005 (9)	0.0050 (9)	0.0029 (9)
C38	0.0309 (11)	0.0303 (10)	0.0301 (10)	0.0003 (9)	−0.0008 (9)	0.0008 (9)
C39	0.0243 (10)	0.0293 (10)	0.0299 (10)	0.0029 (8)	0.0011 (9)	−0.0035 (8)
C40	0.0202 (9)	0.0294 (10)	0.0233 (9)	0.0012 (8)	−0.0018 (8)	−0.0018 (8)
C41	0.0367 (12)	0.0372 (12)	0.0233 (10)	−0.0021 (10)	0.0024 (9)	−0.0005 (9)
C42	0.0441 (15)	0.0485 (15)	0.0434 (14)	0.0079 (13)	−0.0071 (12)	0.0023 (12)
C43	0.0653 (18)	0.0490 (15)	0.0321 (12)	−0.0216 (14)	0.0033 (13)	0.0012 (11)
C44	0.0355 (12)	0.0389 (12)	0.0299 (11)	0.0020 (10)	0.0009 (9)	0.0047 (10)
C45	0.0420 (14)	0.0542 (16)	0.0380 (13)	0.0034 (13)	−0.0100 (11)	0.0024 (12)
C46	0.0497 (17)	0.095 (3)	0.0419 (15)	0.0112 (18)	0.0136 (14)	0.0027 (17)

Geometric parameters (Å, º)

O1—C2	1.367 (3)	C22—C23	1.432 (3)
O1—H1	0.95 (3)	C23—C24	1.364 (3)
O2—C12	1.370 (3)	C24—C25	1.421 (3)
O2—H2	0.95 (4)	C24—H16	0.9500
O3—C22	1.367 (2)	C25—C26	1.415 (3)
O3—H3	0.94 (4)	C25—C30	1.428 (3)
O4—C32	1.363 (3)	C26—C27	1.375 (3)
O4—H4	0.94 (4)	C26—H17	0.9500
O5—C41	1.238 (3)	C27—C28	1.414 (3)
O6—C44	1.221 (3)	C27—H18	0.9500
C1—C2	1.382 (3)	C28—C29	1.365 (3)
C1—C10	1.431 (3)	C28—H19	0.9500
C1—C11	1.492 (3)	C29—C30	1.427 (3)
C2—C3	1.416 (3)	C29—H20	0.9500
C3—C4	1.363 (3)	C31—C32	1.376 (3)
C3—H5	0.9500	C31—C40	1.431 (3)
C4—C5	1.421 (3)	C32—C33	1.421 (3)
C4—H6	0.9500	C33—C34	1.357 (3)
C5—C6	1.416 (3)	C33—H21	0.9500
C5—C10	1.426 (3)	C34—C35	1.421 (3)
C6—C7	1.370 (4)	C34—H26	0.9500
C6—H7	0.9500	C35—C36	1.419 (3)
C7—C8	1.406 (4)	C35—C40	1.433 (3)
C7—H8	0.9500	C36—C37	1.363 (3)
C8—C9	1.374 (3)	C36—H25	0.9500
C8—H9	0.9500	C37—C38	1.413 (3)
C9—C10	1.421 (3)	C37—H24	0.9500
C9—H10	0.9500	C38—C39	1.378 (3)
C11—C12	1.388 (3)	C38—H23	0.9500
C11—C20	1.430 (3)	C39—C40	1.414 (3)
C12—C13	1.428 (3)	C39—H22	0.9500
C13—C14	1.374 (3)	C41—C42	1.490 (4)
C13—C23	1.501 (3)	C41—C43	1.494 (4)
C14—C15	1.414 (3)	C42—H29	0.9800
C14—H11	0.9500	C42—H28	0.9800
C15—C16	1.419 (3)	C42—H27	0.9800
C15—C20	1.423 (3)	C43—H30	0.9800
C16—C17	1.370 (3)	C43—H31	0.9800
C16—H12	0.9500	C43—H32	0.9800
C17—C18	1.415 (3)	C44—C46	1.499 (4)
C17—H13	0.9500	C44—C45	1.499 (4)
C18—C19	1.371 (3)	C45—H33	0.9800
C18—H14	0.9500	C45—H34	0.9800
C19—C20	1.431 (3)	C45—H35	0.9800
C19—H15	0.9500	C46—H36	0.9800
C21—C22	1.392 (3)	C46—H37	0.9800
C21—C30	1.430 (3)	C46—H38	0.9800
C21—C31	1.500 (3)
C2—O1—H1	114 (2)	C26—C25—C30	119.66 (19)
C12—O2—H2	112 (2)	C24—C25—C30	118.55 (18)
C22—O3—H3	111 (2)	C27—C26—C25	120.7 (2)
C32—O4—H4	115 (2)	C27—C26—H17	119.7
C2—C1—C10	118.66 (19)	C25—C26—H17	119.7
C2—C1—C11	120.76 (19)	C26—C27—C28	119.8 (2)
C10—C1—C11	120.31 (18)	C26—C27—H18	120.1
O1—C2—C1	123.77 (19)	C28—C27—H18	120.1
O1—C2—C3	115.36 (19)	C29—C28—C27	120.9 (2)
C1—C2—C3	120.9 (2)	C29—C28—H19	119.6
C4—C3—C2	120.8 (2)	C27—C28—H19	119.6
C4—C3—H5	119.6	C28—C29—C30	121.0 (2)
C2—C3—H5	119.6	C28—C29—H20	119.5
C3—C4—C5	120.9 (2)	C30—C29—H20	119.5
C3—C4—H6	119.6	C29—C30—C25	117.95 (19)
C5—C4—H6	119.6	C29—C30—C21	122.61 (19)
C6—C5—C4	122.0 (2)	C25—C30—C21	119.42 (18)
C6—C5—C10	119.9 (2)	C32—C31—C40	119.11 (19)
C4—C5—C10	118.1 (2)	C32—C31—C21	119.25 (19)
C7—C6—C5	121.0 (2)	C40—C31—C21	121.51 (18)
C7—C6—H7	119.5	O4—C32—C31	123.62 (19)
C5—C6—H7	119.5	O4—C32—C33	115.23 (19)
C6—C7—C8	119.3 (2)	C31—C32—C33	121.1 (2)
C6—C7—H8	120.3	C34—C33—C32	120.3 (2)
C8—C7—H8	120.3	C34—C33—H21	119.8
C9—C8—C7	121.3 (2)	C32—C33—H21	119.8
C9—C8—H9	119.4	C33—C34—C35	120.9 (2)
C7—C8—H9	119.4	C33—C34—H26	119.5
C8—C9—C10	120.9 (2)	C35—C34—H26	119.5
C8—C9—H10	119.6	C36—C35—C34	122.0 (2)
C10—C9—H10	119.6	C36—C35—C40	119.2 (2)
C9—C10—C5	117.6 (2)	C34—C35—C40	118.7 (2)
C9—C10—C1	121.79 (19)	C37—C36—C35	121.4 (2)
C5—C10—C1	120.55 (19)	C37—C36—H25	119.3
C12—C11—C20	119.82 (19)	C35—C36—H25	119.3
C12—C11—C1	121.83 (19)	C36—C37—C38	119.7 (2)
C20—C11—C1	118.35 (17)	C36—C37—H24	120.1
O2—C12—C11	117.40 (19)	C38—C37—H24	120.1
O2—C12—C13	121.61 (18)	C39—C38—C37	120.5 (2)
C11—C12—C13	120.99 (19)	C39—C38—H23	119.8
C14—C13—C12	118.50 (18)	C37—C38—H23	119.8
C14—C13—C23	117.76 (19)	C38—C39—C40	121.3 (2)
C12—C13—C23	123.68 (19)	C38—C39—H22	119.4
C13—C14—C15	122.66 (19)	C40—C39—H22	119.4
C13—C14—H11	118.7	C39—C40—C31	122.57 (19)
C15—C14—H11	118.7	C39—C40—C35	118.0 (2)
C14—C15—C16	121.28 (19)	C31—C40—C35	119.44 (19)
C14—C15—C20	118.46 (19)	O5—C41—C42	120.8 (2)
C16—C15—C20	120.25 (19)	O5—C41—C43	121.2 (2)
C17—C16—C15	120.3 (2)	C42—C41—C43	117.9 (2)
C17—C16—H12	119.8	C41—C42—H29	109.5
C15—C16—H12	119.8	C41—C42—H28	109.5
C16—C17—C18	120.1 (2)	H29—C42—H28	109.5
C16—C17—H13	119.9	C41—C42—H27	109.5
C18—C17—H13	119.9	H29—C42—H27	109.5
C19—C18—C17	120.8 (2)	H28—C42—H27	109.5
C19—C18—H14	119.6	C41—C43—H30	109.5
C17—C18—H14	119.6	C41—C43—H31	109.5
C18—C19—C20	120.7 (2)	H30—C43—H31	109.5
C18—C19—H15	119.6	C41—C43—H32	109.5
C20—C19—H15	119.6	H30—C43—H32	109.5
C15—C20—C11	119.40 (18)	H31—C43—H32	109.5
C15—C20—C19	117.74 (19)	O6—C44—C46	121.1 (2)
C11—C20—C19	122.85 (19)	O6—C44—C45	121.4 (2)
C22—C21—C30	119.51 (18)	C46—C44—C45	117.5 (2)
C22—C21—C31	120.49 (18)	C44—C45—H33	109.5
C30—C21—C31	119.99 (18)	C44—C45—H34	109.5
O3—C22—C21	117.80 (18)	H33—C45—H34	109.5
O3—C22—C23	121.07 (18)	C44—C45—H35	109.5
C21—C22—C23	121.13 (18)	H33—C45—H35	109.5
C24—C23—C22	118.80 (18)	H34—C45—H35	109.5
C24—C23—C13	118.97 (19)	C44—C46—H36	109.5
C22—C23—C13	122.11 (18)	C44—C46—H37	109.5
C23—C24—C25	122.46 (19)	H36—C46—H37	109.5
C23—C24—H16	118.8	C44—C46—H38	109.5
C25—C24—H16	118.8	H36—C46—H38	109.5
C26—C25—C24	121.8 (2)	H37—C46—H38	109.5
C10—C1—C2—O1	178.28 (18)	C30—C21—C22—C23	−3.3 (3)
C11—C1—C2—O1	4.2 (3)	C31—C21—C22—C23	175.24 (18)
C10—C1—C2—C3	−0.9 (3)	O3—C22—C23—C24	−176.10 (19)
C11—C1—C2—C3	−174.98 (19)	C21—C22—C23—C24	4.2 (3)
O1—C2—C3—C4	−178.8 (2)	O3—C22—C23—C13	−0.3 (3)
C1—C2—C3—C4	0.5 (3)	C21—C22—C23—C13	180.0 (2)
C2—C3—C4—C5	0.8 (3)	C14—C13—C23—C24	54.9 (3)
C3—C4—C5—C6	177.6 (2)	C12—C13—C23—C24	−122.1 (2)
C3—C4—C5—C10	−1.6 (3)	C14—C13—C23—C22	−120.9 (2)
C4—C5—C6—C7	−178.4 (2)	C12—C13—C23—C22	62.1 (3)
C10—C5—C6—C7	0.8 (3)	C22—C23—C24—C25	−1.8 (3)
C5—C6—C7—C8	−1.1 (3)	C13—C23—C24—C25	−177.7 (2)
C6—C7—C8—C9	0.0 (3)	C23—C24—C25—C26	178.8 (2)
C7—C8—C9—C10	1.5 (3)	C23—C24—C25—C30	−1.3 (3)
C8—C9—C10—C5	−1.8 (3)	C24—C25—C26—C27	−178.5 (2)
C8—C9—C10—C1	176.9 (2)	C30—C25—C26—C27	1.5 (3)
C6—C5—C10—C9	0.7 (3)	C25—C26—C27—C28	−2.0 (4)
C4—C5—C10—C9	179.86 (19)	C26—C27—C28—C29	0.1 (4)
C6—C5—C10—C1	−178.02 (19)	C27—C28—C29—C30	2.4 (4)
C4—C5—C10—C1	1.2 (3)	C28—C29—C30—C25	−2.8 (3)
C2—C1—C10—C9	−178.58 (19)	C28—C29—C30—C21	176.0 (2)
C11—C1—C10—C9	−4.5 (3)	C26—C25—C30—C29	0.8 (3)
C2—C1—C10—C5	0.0 (3)	C24—C25—C30—C29	−179.1 (2)
C11—C1—C10—C5	174.15 (19)	C26—C25—C30—C21	−178.0 (2)
C2—C1—C11—C12	−78.6 (3)	C24—C25—C30—C21	2.1 (3)
C10—C1—C11—C12	107.4 (2)	C22—C21—C30—C29	−178.6 (2)
C2—C1—C11—C20	102.1 (2)	C31—C21—C30—C29	2.8 (3)
C10—C1—C11—C20	−71.8 (3)	C22—C21—C30—C25	0.2 (3)
C20—C11—C12—O2	177.95 (18)	C31—C21—C30—C25	−178.41 (19)
C1—C11—C12—O2	−1.3 (3)	C22—C21—C31—C32	−79.1 (3)
C20—C11—C12—C13	−2.6 (3)	C30—C21—C31—C32	99.4 (2)
C1—C11—C12—C13	178.17 (18)	C22—C21—C31—C40	105.1 (2)
O2—C12—C13—C14	−176.00 (19)	C30—C21—C31—C40	−76.3 (3)
C11—C12—C13—C14	4.5 (3)	C40—C31—C32—O4	173.31 (18)
O2—C12—C13—C23	1.0 (3)	C21—C31—C32—O4	−2.5 (3)
C11—C12—C13—C23	−178.4 (2)	C40—C31—C32—C33	−6.1 (3)
C12—C13—C14—C15	−2.8 (3)	C21—C31—C32—C33	178.02 (19)
C23—C13—C14—C15	−179.95 (19)	O4—C32—C33—C34	−175.1 (2)
C13—C14—C15—C16	179.96 (19)	C31—C32—C33—C34	4.4 (3)
C13—C14—C15—C20	−0.9 (3)	C32—C33—C34—C35	0.6 (3)
C14—C15—C16—C17	179.0 (2)	C33—C34—C35—C36	174.3 (2)
C20—C15—C16—C17	−0.1 (3)	C33—C34—C35—C40	−3.6 (3)
C15—C16—C17—C18	−1.1 (3)	C34—C35—C36—C37	−178.6 (2)
C16—C17—C18—C19	0.6 (4)	C40—C35—C36—C37	−0.7 (3)
C17—C18—C19—C20	1.0 (4)	C35—C36—C37—C38	−0.1 (4)
C14—C15—C20—C11	2.9 (3)	C36—C37—C38—C39	0.0 (4)
C16—C15—C20—C11	−178.0 (2)	C37—C38—C39—C40	1.1 (3)
C14—C15—C20—C19	−177.4 (2)	C38—C39—C40—C31	175.9 (2)
C16—C15—C20—C19	1.7 (3)	C38—C39—C40—C35	−1.9 (3)
C12—C11—C20—C15	−1.2 (3)	C32—C31—C40—C39	−174.8 (2)
C1—C11—C20—C15	178.08 (19)	C21—C31—C40—C39	1.0 (3)
C12—C11—C20—C19	179.2 (2)	C32—C31—C40—C35	3.0 (3)
C1—C11—C20—C19	−1.6 (3)	C21—C31—C40—C35	178.74 (18)
C18—C19—C20—C15	−2.1 (3)	C36—C35—C40—C39	1.7 (3)
C18—C19—C20—C11	177.5 (2)	C34—C35—C40—C39	179.7 (2)
C30—C21—C22—O3	176.92 (18)	C36—C35—C40—C31	−176.16 (19)
C31—C21—C22—O3	−4.5 (3)	C34—C35—C40—C31	1.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.95 (3)	1.94 (3)	2.854 (2)	160 (3)
O2—H2···O6	0.95 (4)	1.96 (4)	2.885 (2)	164 (3)
O3—H3···O5	0.94 (4)	1.98 (4)	2.889 (2)	163 (3)
O4—H4···O6	0.94 (4)	1.92 (4)	2.803 (2)	156 (3)