Conspicuous hydrogen bonds linking (R,R)-3′,3′′-bisBINOL, methyl 2-methyl­phenyl (R)-sulfoxide and chloro­form in the 1:2:1 complex

The asymmetric unit of the crystal structure of the title compound, C₄₀H₂₆O₄·2C₈H₁₀OS·CHCl₃, consists of one mol­ecule of (R,R)-3′,3′′-bisBINOL [(R,R)-1,1′:3′,3′′:1,1-quater-2-naphthol], two mol­ecules of methyl 2-methyl­phenyl (R)-sulfoxide and one mol­ecule of chloro­form. The central feature of the structure is the two sets of O—H...O...H—O hydrogen bonds, linking pairs of hydroxy groups of (R,R)-3′,3′′-bisBINOL via the sulfoxide O atoms and thus forming an 18-membered pseudo-macrocycle involving one bisBINOL and two sulfoxide mol­ecules. The chloro­form mol­ecule is linked to one of the hydroxy O atoms of the bisBINOL via a C—H...O interaction.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.088
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C8 H10 O S
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              C H Cl3

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           27.50
           From the CIF: _reflns_number_total              11046
           Count of symmetry unique reflns         6130
           Completeness (_total/calc)            180.20%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      4916
           Fraction of Friedel pairs measured     0.802
           Are heavy atom types Z>Si present          yes

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

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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

(I)

Crystal data

C40H26O4·2C8H10OS·CHCl3	F(000) = 2080
Mr = 998.42	Dx = 1.366 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 41152 reflections
a = 13.8789 (15) Å	θ = 3.1–27.5°
b = 15.410 (2) Å	µ = 0.33 mm^−1
c = 22.705 (2) Å	T = 93 K
V = 4856.0 (10) Å^3	Block, yellow
Z = 4	0.8 × 0.8 × 0.6 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	10476 reflections with I > 2σ(I)
ω scans	Rint = 0.040
Absorption correction: multi-scan (ABSCOR; Higashi, 1995).	θmax = 27.5°, θmin = 3°
Tmin = 0.779, Tmax = 0.828	h = −15→18
40838 measured reflections	k = −19→19
11046 independent reflections	l = −29→28

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 3.7498P] where P = (Fo^2 + 2Fc^2)/3
Least-squares matrix: full	(Δ/σ)max = 0.007
R[F^2 > 2σ(F^2)] = 0.033	Δρmax = 0.27 e Å^−3
wR(F^2) = 0.088	Δρmin = −0.37 e Å^−3
S = 1.05	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
11046 reflections	Extinction coefficient: 0.00146 (18)
641 parameters	Absolute structure: Flack (1983), 4963 Friedel pairs
0 restraints	Absolute structure parameter: −0.01 (4)
H atoms treated by a mixture of independent and constrained refinement

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
Cl1	0.76606 (4)	0.59308 (4)	−0.08901 (3)	0.03354 (12)
Cl2	0.87539 (4)	0.48607 (5)	−0.16979 (3)	0.04138 (15)
Cl3	0.66691 (4)	0.47732 (4)	−0.16851 (3)	0.03682 (14)
S2	0.66926 (4)	0.19513 (4)	0.24223 (2)	0.02850 (12)
S1	0.91769 (4)	0.15684 (3)	−0.08317 (2)	0.02370 (11)
O1	0.71990 (11)	0.32386 (10)	−0.04027 (6)	0.0236 (3)
H1	0.768 (3)	0.293 (2)	−0.0289 (14)	0.056 (10)*
O2	0.75189 (10)	0.24517 (10)	0.10786 (7)	0.0232 (3)
H2	0.760 (2)	0.2003 (18)	0.1284 (12)	0.031 (7)*
O3	0.85372 (11)	0.06919 (9)	0.05650 (6)	0.0218 (3)
H3	0.8564 (19)	0.1166 (17)	0.0381 (12)	0.026 (7)*
O4	0.68286 (11)	−0.02080 (10)	0.13120 (7)	0.0256 (3)
H4	0.712 (2)	0.023 (2)	0.1480 (13)	0.040 (8)*
O6	0.71915 (12)	0.13309 (10)	0.20096 (7)	0.0287 (3)
O5	0.84929 (10)	0.18993 (10)	−0.03659 (6)	0.0232 (3)
C16	1.10223 (14)	0.37986 (13)	0.02766 (9)	0.0208 (4)
H12	1.1613	0.3515	0.0365	0.025*
C19	0.93000 (15)	0.46618 (12)	0.00364 (9)	0.0205 (4)
H15	0.8723	0.4974	−0.0039	0.025*
C18	1.01517 (16)	0.49573 (14)	−0.01913 (10)	0.0250 (4)
H14	1.0154	0.5457	−0.0436	0.03*
C17	1.10242 (15)	0.45300 (13)	−0.00673 (10)	0.0236 (4)
H13	1.1613	0.4748	−0.0221	0.028*
C20	0.92647 (14)	0.38986 (12)	0.03829 (8)	0.0171 (4)
C15	1.01467 (14)	0.34637 (13)	0.05005 (8)	0.0177 (4)
C14	1.01163 (14)	0.26826 (12)	0.08288 (9)	0.0171 (4)
H11	1.0703	0.2394	0.0919	0.02*
C13	0.92695 (14)	0.23328 (12)	0.10183 (8)	0.0161 (3)
C12	0.83873 (13)	0.27759 (12)	0.09004 (8)	0.0171 (4)
C11	0.83799 (14)	0.35563 (12)	0.06029 (8)	0.0174 (4)
C23	0.92672 (13)	0.15116 (13)	0.13659 (8)	0.0175 (4)
C22	0.88899 (14)	0.07296 (13)	0.11214 (9)	0.0181 (4)
C21	0.88716 (14)	−0.00289 (13)	0.14483 (8)	0.0188 (4)
C30	0.92327 (14)	−0.00206 (13)	0.20406 (9)	0.0195 (4)
C25	0.96120 (14)	0.07575 (13)	0.22815 (9)	0.0196 (4)
C24	0.96269 (14)	0.15102 (13)	0.19265 (9)	0.0189 (4)
H16	0.9894	0.203	0.2082	0.023*
C26	0.99385 (14)	0.07689 (14)	0.28750 (9)	0.0226 (4)
H17	1.0199	0.1288	0.3035	0.027*
C27	0.98827 (16)	0.00423 (15)	0.32180 (10)	0.0264 (4)
H18	1.0088	0.006	0.3617	0.032*
C28	0.95200 (16)	−0.07321 (15)	0.29775 (10)	0.0281 (5)
H19	0.9491	−0.1238	0.3216	0.034*
C29	0.92074 (16)	−0.07697 (14)	0.24047 (9)	0.0243 (4)
H20	0.8972	−0.1302	0.225	0.029*
C31	0.84259 (16)	−0.08173 (13)	0.11912 (8)	0.0217 (4)
C32	0.74329 (15)	−0.08477 (13)	0.11257 (9)	0.0230 (4)
C33	0.69741 (16)	−0.15657 (14)	0.08630 (10)	0.0269 (4)
H21	0.6295	−0.1561	0.081	0.032*
C34	0.74970 (18)	−0.22689 (14)	0.06837 (9)	0.0293 (5)
H22	0.7177	−0.2748	0.0507	0.035*
C35	0.85121 (17)	−0.22914 (13)	0.07580 (9)	0.0273 (5)
C40	0.89814 (16)	−0.15521 (14)	0.10029 (9)	0.0242 (4)
C39	1.00001 (17)	−0.15786 (15)	0.10592 (10)	0.0291 (5)
H26	1.033	−0.1089	0.1214	0.035*
C38	1.05137 (18)	−0.22954 (16)	0.08949 (12)	0.0353 (5)
H25	1.1194	−0.2298	0.0939	0.042*
C37	1.0044 (2)	−0.30330 (16)	0.06599 (11)	0.0367 (6)
H24	1.0406	−0.353	0.0548	0.044*
C36	0.9068 (2)	−0.30230 (15)	0.05950 (10)	0.0339 (5)
H23	0.8753	−0.3518	0.0437	0.041*
C7	0.64822 (17)	0.60202 (15)	0.16331 (11)	0.0305 (5)
H8	0.6261	0.6463	0.1891	0.037*
C8	0.73139 (18)	0.55454 (15)	0.17738 (10)	0.0302 (5)
H9	0.7656	0.5674	0.2126	0.036*
C9	0.76393 (15)	0.48993 (14)	0.14105 (9)	0.0242 (4)
H10	0.8203	0.4584	0.1513	0.029*
C10	0.71398 (14)	0.46983 (12)	0.08828 (9)	0.0195 (4)
C5	0.62956 (14)	0.51794 (13)	0.07400 (9)	0.0207 (4)
C4	0.57816 (15)	0.49745 (13)	0.02183 (9)	0.0223 (4)
H6	0.522	0.5295	0.0119	0.027*
C6	0.59910 (16)	0.58473 (14)	0.11271 (10)	0.0262 (4)
H7	0.5436	0.618	0.1032	0.031*
C3	0.60847 (15)	0.43230 (14)	−0.01405 (9)	0.0218 (4)
H5	0.5729	0.4183	−0.0485	0.026*
C2	0.69263 (14)	0.38552 (12)	−0.00011 (9)	0.0184 (4)
C1	0.74601 (14)	0.40290 (12)	0.04950 (8)	0.0178 (4)
C57	0.77114 (17)	0.49217 (15)	−0.12591 (10)	0.0292 (5)
H47	0.773 (2)	0.4482 (17)	−0.0964 (12)	0.035*
C54	0.73992 (17)	0.08022 (16)	0.32340 (10)	0.0320 (5)
H30	0.7725	0.0546	0.291	0.038*
C51	0.64497 (17)	0.15689 (18)	0.41738 (11)	0.0361 (5)
H27	0.6137	0.1833	0.45	0.043*
C52	0.70371 (18)	0.0857 (2)	0.42662 (11)	0.0424 (6)
H28	0.712	0.0637	0.4654	0.051*
C53	0.75072 (18)	0.04616 (19)	0.37987 (11)	0.0398 (6)
H29	0.7898	−0.0036	0.3863	0.048*
C50	0.63072 (16)	0.19054 (15)	0.36131 (10)	0.0279 (5)
C49	0.68156 (16)	0.15143 (15)	0.31513 (9)	0.0256 (4)
C55	0.56062 (17)	0.26421 (16)	0.35160 (11)	0.0344 (5)
H32	0.531	0.2804	0.3892	0.052*
H33	0.5104	0.2457	0.324	0.052*
H31	0.595	0.3143	0.3353	0.052*
C56	0.7547 (2)	0.28362 (18)	0.25142 (12)	0.0465 (7)
H35	0.8187	0.2599	0.2599	0.07*
H36	0.734	0.3206	0.2842	0.07*
H34	0.7573	0.318	0.2152	0.07*
C46	0.78717 (16)	0.23424 (15)	−0.15804 (9)	0.0257 (4)
C41	0.86415 (15)	0.17762 (13)	−0.15361 (9)	0.0220 (4)
C42	0.90022 (17)	0.13387 (15)	−0.20290 (10)	0.0293 (5)
C43	0.85786 (17)	0.15253 (16)	−0.25703 (10)	0.0301 (5)
H37	0.8815	0.1247	−0.2914	0.036*
C44	0.78244 (17)	0.21035 (14)	−0.26209 (9)	0.0269 (4)
H38	0.7554	0.2224	−0.2996	0.032*
C45	0.74636 (17)	0.25067 (15)	−0.21256 (10)	0.0289 (5)
H39	0.6936	0.2897	−0.2158	0.035*
C47	0.9803 (2)	0.0681 (2)	−0.19856 (13)	0.0531 (8)
H42	0.9832	0.0342	−0.235	0.08*
H43	0.9681	0.0293	−0.1652	0.08*
H41	1.0418	0.0982	−0.1926	0.08*
C48	1.01104 (16)	0.23655 (18)	−0.08747 (11)	0.0343 (5)
H45	0.9823	0.2942	−0.0923	0.051*
H46	1.0526	0.2239	−0.1213	0.051*
H44	1.0494	0.2352	−0.0512	0.051*
H40	0.765 (2)	0.2579 (18)	−0.1232 (13)	0.039 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0371 (3)	0.0283 (3)	0.0353 (3)	−0.0014 (2)	−0.0057 (2)	0.0014 (2)
Cl2	0.0292 (3)	0.0483 (4)	0.0467 (4)	−0.0031 (3)	0.0078 (3)	0.0003 (3)
Cl3	0.0276 (3)	0.0467 (3)	0.0362 (3)	−0.0012 (3)	−0.0017 (2)	−0.0096 (3)
S2	0.0315 (3)	0.0281 (3)	0.0260 (3)	0.0033 (2)	0.0052 (2)	0.0039 (2)
S1	0.0244 (2)	0.0281 (2)	0.0186 (2)	0.0064 (2)	0.00005 (19)	−0.0006 (2)
O1	0.0224 (7)	0.0266 (8)	0.0217 (7)	0.0054 (6)	−0.0035 (6)	−0.0066 (6)
O2	0.0177 (7)	0.0220 (7)	0.0300 (8)	−0.0015 (6)	0.0026 (6)	0.0086 (6)
O3	0.0297 (8)	0.0192 (7)	0.0166 (7)	−0.0031 (6)	−0.0026 (6)	0.0036 (6)
O4	0.0246 (8)	0.0262 (8)	0.0260 (7)	−0.0029 (6)	−0.0029 (6)	0.0035 (6)
O6	0.0345 (9)	0.0279 (8)	0.0237 (7)	0.0008 (7)	0.0055 (6)	0.0004 (6)
O5	0.0230 (7)	0.0286 (7)	0.0179 (7)	0.0031 (6)	0.0022 (5)	0.0001 (6)
C16	0.0178 (9)	0.0225 (9)	0.0220 (9)	−0.0013 (7)	0.0006 (7)	−0.0014 (8)
C19	0.0224 (10)	0.0174 (9)	0.0218 (9)	0.0001 (8)	−0.0012 (8)	0.0009 (8)
C18	0.0288 (11)	0.0204 (10)	0.0259 (10)	−0.0044 (8)	−0.0025 (8)	0.0070 (8)
C17	0.0212 (10)	0.0232 (10)	0.0265 (10)	−0.0059 (8)	0.0028 (8)	0.0021 (8)
C20	0.0199 (9)	0.0147 (8)	0.0166 (9)	−0.0024 (7)	0.0009 (7)	−0.0023 (7)
C15	0.0163 (9)	0.0206 (9)	0.0162 (8)	−0.0008 (7)	−0.0010 (7)	−0.0023 (8)
C14	0.0177 (9)	0.0142 (8)	0.0192 (9)	0.0006 (7)	−0.0007 (7)	−0.0027 (7)
C13	0.0203 (9)	0.0131 (8)	0.0150 (8)	−0.0006 (7)	−0.0004 (7)	−0.0006 (7)
C12	0.0160 (8)	0.0171 (8)	0.0183 (8)	−0.0011 (7)	0.0006 (7)	0.0003 (7)
C11	0.0171 (9)	0.0200 (9)	0.0152 (8)	0.0004 (7)	−0.0006 (7)	−0.0017 (7)
C23	0.0160 (8)	0.0182 (9)	0.0184 (9)	0.0015 (7)	0.0021 (7)	0.0020 (7)
C22	0.0178 (9)	0.0189 (9)	0.0177 (9)	0.0010 (7)	0.0003 (7)	0.0002 (7)
C21	0.0202 (9)	0.0185 (9)	0.0177 (9)	0.0000 (7)	−0.0006 (7)	0.0001 (7)
C30	0.0179 (9)	0.0208 (9)	0.0198 (9)	0.0014 (7)	−0.0003 (7)	0.0013 (7)
C25	0.0166 (9)	0.0222 (10)	0.0199 (9)	0.0024 (7)	−0.0013 (7)	0.0007 (8)
C24	0.0171 (9)	0.0187 (9)	0.0209 (9)	0.0006 (7)	−0.0016 (7)	−0.0013 (7)
C26	0.0209 (10)	0.0268 (10)	0.0200 (10)	0.0006 (8)	−0.0019 (7)	0.0002 (8)
C27	0.0270 (10)	0.0307 (11)	0.0214 (10)	0.0037 (9)	−0.0039 (8)	0.0023 (9)
C28	0.0299 (11)	0.0306 (11)	0.0238 (10)	0.0034 (9)	−0.0023 (9)	0.0107 (9)
C29	0.0272 (10)	0.0205 (9)	0.0252 (10)	−0.0001 (8)	−0.0008 (8)	0.0033 (8)
C31	0.0292 (10)	0.0196 (9)	0.0163 (9)	−0.0041 (8)	−0.0009 (8)	0.0040 (7)
C32	0.0292 (11)	0.0200 (9)	0.0199 (9)	−0.0028 (8)	−0.0017 (8)	0.0068 (8)
C33	0.0305 (11)	0.0277 (10)	0.0224 (10)	−0.0080 (9)	−0.0063 (8)	0.0066 (9)
C34	0.0433 (14)	0.0248 (10)	0.0198 (10)	−0.0119 (10)	−0.0068 (9)	0.0020 (8)
C35	0.0408 (13)	0.0192 (10)	0.0218 (10)	−0.0060 (9)	−0.0007 (9)	0.0029 (8)
C40	0.0341 (11)	0.0197 (9)	0.0188 (9)	−0.0036 (9)	0.0004 (8)	0.0021 (8)
C39	0.0337 (12)	0.0206 (10)	0.0329 (12)	−0.0019 (9)	0.0029 (9)	−0.0023 (9)
C38	0.0333 (12)	0.0325 (12)	0.0400 (13)	0.0014 (10)	0.0039 (10)	−0.0037 (11)
C37	0.0501 (16)	0.0230 (11)	0.0370 (13)	0.0022 (11)	0.0043 (11)	−0.0050 (10)
C36	0.0547 (15)	0.0184 (10)	0.0285 (11)	−0.0049 (10)	−0.0019 (11)	−0.0019 (9)
C7	0.0297 (12)	0.0282 (11)	0.0336 (12)	0.0036 (9)	0.0031 (9)	−0.0121 (9)
C8	0.0298 (11)	0.0337 (12)	0.0271 (11)	0.0014 (10)	−0.0043 (9)	−0.0085 (9)
C9	0.0222 (10)	0.0275 (10)	0.0229 (10)	0.0016 (9)	−0.0048 (8)	−0.0024 (8)
C10	0.0194 (9)	0.0183 (9)	0.0208 (9)	−0.0017 (7)	0.0008 (7)	0.0002 (8)
C5	0.0187 (9)	0.0175 (9)	0.0259 (10)	0.0001 (7)	0.0006 (7)	0.0000 (8)
C4	0.0194 (9)	0.0210 (10)	0.0265 (10)	0.0025 (8)	−0.0018 (8)	0.0029 (8)
C6	0.0248 (10)	0.0198 (10)	0.0341 (11)	0.0059 (8)	0.0005 (9)	−0.0033 (9)
C3	0.0195 (9)	0.0262 (10)	0.0197 (10)	−0.0007 (8)	−0.0034 (7)	0.0011 (8)
C2	0.0189 (9)	0.0164 (9)	0.0199 (9)	−0.0016 (7)	0.0013 (7)	0.0002 (7)
C1	0.0176 (9)	0.0159 (8)	0.0201 (9)	−0.0021 (7)	0.0001 (7)	0.0025 (7)
C57	0.0308 (11)	0.0292 (11)	0.0278 (11)	−0.0004 (10)	0.0007 (9)	0.0024 (9)
C54	0.0287 (11)	0.0399 (13)	0.0273 (11)	0.0044 (10)	0.0049 (9)	0.0028 (10)
C51	0.0265 (11)	0.0551 (15)	0.0267 (11)	−0.0082 (11)	0.0032 (9)	−0.0063 (12)
C52	0.0327 (13)	0.0699 (19)	0.0245 (12)	−0.0022 (13)	−0.0021 (9)	0.0066 (12)
C53	0.0301 (13)	0.0531 (16)	0.0360 (13)	0.0065 (11)	−0.0001 (10)	0.0127 (12)
C50	0.0207 (10)	0.0314 (11)	0.0317 (11)	−0.0082 (9)	0.0020 (8)	−0.0050 (9)
C49	0.0243 (10)	0.0310 (11)	0.0215 (10)	−0.0035 (9)	0.0019 (8)	0.0016 (8)
C55	0.0284 (12)	0.0346 (12)	0.0402 (13)	−0.0043 (10)	0.0099 (10)	−0.0070 (10)
C56	0.0615 (19)	0.0374 (14)	0.0406 (14)	−0.0131 (13)	0.0173 (13)	−0.0080 (11)
C46	0.0316 (11)	0.0280 (11)	0.0175 (9)	0.0035 (9)	−0.0013 (8)	−0.0042 (8)
C41	0.0254 (10)	0.0223 (10)	0.0183 (9)	0.0001 (8)	−0.0001 (7)	−0.0010 (8)
C42	0.0294 (11)	0.0313 (11)	0.0272 (11)	0.0044 (9)	0.0010 (9)	−0.0062 (9)
C43	0.0332 (12)	0.0376 (12)	0.0194 (10)	−0.0032 (10)	0.0032 (8)	−0.0081 (9)
C44	0.0333 (12)	0.0255 (10)	0.0220 (10)	−0.0070 (9)	−0.0012 (9)	−0.0002 (8)
C45	0.0326 (12)	0.0296 (11)	0.0244 (10)	0.0044 (9)	−0.0048 (9)	−0.0026 (9)
C47	0.0492 (17)	0.073 (2)	0.0368 (15)	0.0310 (16)	−0.0039 (13)	−0.0206 (14)
C48	0.0238 (11)	0.0530 (15)	0.0260 (11)	−0.0065 (10)	−0.0012 (9)	−0.0025 (11)

Geometric parameters (Å, º)

Cl1—C57	1.768 (2)	C40—C39	1.420 (3)
Cl2—C57	1.759 (2)	C39—C38	1.366 (3)
Cl3—C57	1.755 (2)	C39—H26	0.95
S2—O6	1.5072 (16)	C38—C37	1.415 (3)
S2—C49	1.795 (2)	C38—H25	0.95
S2—C56	1.819 (3)	C37—C36	1.363 (4)
S1—O5	1.5099 (15)	C37—H24	0.95
S1—C48	1.788 (2)	C36—H23	0.95
S1—C41	1.792 (2)	C7—C6	1.362 (3)
O1—C2	1.370 (2)	C7—C8	1.403 (3)
O1—H1	0.86 (4)	C7—H8	0.95
O2—C12	1.366 (2)	C8—C9	1.369 (3)
O2—H2	0.84 (3)	C8—H9	0.95
O3—C22	1.356 (2)	C9—C10	1.418 (3)
O3—H3	0.84 (3)	C9—H10	0.95
O4—C32	1.362 (3)	C10—C5	1.424 (3)
O4—H4	0.87 (3)	C10—C1	1.427 (3)
C16—C17	1.371 (3)	C5—C6	1.418 (3)
C16—C15	1.415 (3)	C5—C4	1.418 (3)
C16—H12	0.95	C4—C3	1.360 (3)
C19—C18	1.368 (3)	C4—H6	0.95
C19—C20	1.416 (3)	C6—H7	0.95
C19—H15	0.95	C3—C2	1.409 (3)
C18—C17	1.407 (3)	C3—H5	0.95
C18—H14	0.95	C2—C1	1.375 (3)
C17—H13	0.95	C57—H47	0.95 (3)
C20—C15	1.421 (3)	C54—C49	1.377 (3)
C20—C11	1.427 (3)	C54—C53	1.393 (3)
C15—C14	1.416 (3)	C54—H30	0.95
C14—C13	1.363 (3)	C51—C52	1.383 (4)
C14—H11	0.95	C51—C50	1.389 (3)
C13—C12	1.427 (3)	C51—H27	0.95
C13—C23	1.491 (3)	C52—C53	1.387 (4)
C12—C11	1.379 (3)	C52—H28	0.95
C11—C1	1.490 (3)	C53—H29	0.95
C23—C24	1.367 (3)	C50—C49	1.400 (3)
C23—C22	1.426 (3)	C50—C55	1.511 (3)
C22—C21	1.385 (3)	C55—H32	0.98
C21—C30	1.435 (3)	C55—H33	0.98
C21—C31	1.483 (3)	C55—H31	0.98
C30—C25	1.419 (3)	C56—H35	0.98
C30—C29	1.420 (3)	C56—H36	0.98
C25—C24	1.413 (3)	C56—H34	0.98
C25—C26	1.422 (3)	C46—C41	1.383 (3)
C24—H16	0.95	C46—C45	1.385 (3)
C26—C27	1.366 (3)	C46—H40	0.93 (3)
C26—H17	0.95	C41—C42	1.399 (3)
C27—C28	1.406 (3)	C42—C43	1.392 (3)
C27—H18	0.95	C42—C47	1.507 (3)
C28—C29	1.372 (3)	C43—C44	1.379 (3)
C28—H19	0.95	C43—H37	0.95
C29—H20	0.95	C44—C45	1.379 (3)
C31—C32	1.387 (3)	C44—H38	0.95
C31—C40	1.435 (3)	C45—H39	0.95
C32—C33	1.409 (3)	C47—H42	0.98
C33—C34	1.366 (3)	C47—H43	0.98
C33—H21	0.95	C47—H41	0.98
C34—C35	1.419 (3)	C48—H45	0.98
C34—H22	0.95	C48—H46	0.98
C35—C36	1.415 (3)	C48—H44	0.98
C35—C40	1.425 (3)
O6—S2—C49	106.96 (10)	C37—C36—H23	119.3
O6—S2—C56	104.32 (11)	C35—C36—H23	119.3
C49—S2—C56	96.52 (12)	C6—C7—C8	120.1 (2)
O5—S1—C48	105.18 (10)	C6—C7—H8	119.9
O5—S1—C41	107.70 (9)	C8—C7—H8	119.9
C48—S1—C41	97.41 (11)	C9—C8—C7	120.9 (2)
C2—O1—H1	113 (2)	C9—C8—H9	119.6
C12—O2—H2	110.5 (19)	C7—C8—H9	119.6
C22—O3—H3	114.1 (18)	C8—C9—C10	120.4 (2)
C32—O4—H4	114.2 (19)	C8—C9—H10	119.8
C17—C16—C15	120.40 (19)	C10—C9—H10	119.8
C17—C16—H12	119.8	C9—C10—C5	118.74 (18)
C15—C16—H12	119.8	C9—C10—C1	121.78 (18)
C18—C19—C20	121.09 (19)	C5—C10—C1	119.48 (18)
C18—C19—H15	119.5	C6—C5—C4	121.96 (19)
C20—C19—H15	119.5	C6—C5—C10	118.82 (19)
C19—C18—C17	120.81 (19)	C4—C5—C10	119.22 (18)
C19—C18—H14	119.6	C3—C4—C5	120.61 (19)
C17—C18—H14	119.6	C3—C4—H6	119.7
C16—C17—C18	119.80 (19)	C5—C4—H6	119.7
C16—C17—H13	120.1	C7—C6—C5	121.0 (2)
C18—C17—H13	120.1	C7—C6—H7	119.5
C19—C20—C15	117.80 (18)	C5—C6—H7	119.5
C19—C20—C11	122.10 (18)	C4—C3—C2	119.98 (19)
C15—C20—C11	120.09 (17)	C4—C3—H5	120
C16—C15—C14	121.64 (18)	C2—C3—H5	120
C16—C15—C20	120.03 (18)	O1—C2—C1	122.12 (17)
C14—C15—C20	118.30 (17)	O1—C2—C3	115.73 (17)
C13—C14—C15	121.86 (17)	C1—C2—C3	122.10 (18)
C13—C14—H11	119.1	C2—C1—C10	118.59 (18)
C15—C14—H11	119.1	C2—C1—C11	120.08 (17)
C14—C13—C12	119.44 (17)	C10—C1—C11	121.25 (17)
C14—C13—C23	120.30 (17)	Cl3—C57—Cl2	111.02 (13)
C12—C13—C23	120.22 (17)	Cl3—C57—Cl1	110.06 (13)
O2—C12—C11	117.22 (17)	Cl2—C57—Cl1	110.38 (13)
O2—C12—C13	121.76 (16)	Cl3—C57—H47	108.1 (17)
C11—C12—C13	121.01 (17)	Cl2—C57—H47	110.1 (17)
C12—C11—C20	119.17 (17)	Cl1—C57—H47	107.1 (16)
C12—C11—C1	120.87 (17)	C49—C54—C53	119.3 (2)
C20—C11—C1	119.94 (16)	C49—C54—H30	120.4
C24—C23—C22	119.67 (18)	C53—C54—H30	120.4
C24—C23—C13	119.56 (18)	C52—C51—C50	121.3 (2)
C22—C23—C13	120.77 (17)	C52—C51—H27	119.4
O3—C22—C21	117.17 (17)	C50—C51—H27	119.4
O3—C22—C23	122.09 (17)	C51—C52—C53	120.6 (2)
C21—C22—C23	120.74 (18)	C51—C52—H28	119.7
C22—C21—C30	119.23 (18)	C53—C52—H28	119.7
C22—C21—C31	119.22 (17)	C52—C53—C54	119.2 (2)
C30—C21—C31	121.45 (17)	C52—C53—H29	120.4
C25—C30—C29	118.13 (18)	C54—C53—H29	120.4
C25—C30—C21	119.88 (17)	C51—C50—C49	117.0 (2)
C29—C30—C21	121.97 (18)	C51—C50—C55	120.4 (2)
C24—C25—C30	118.64 (18)	C49—C50—C55	122.6 (2)
C24—C25—C26	121.73 (19)	C54—C49—C50	122.5 (2)
C30—C25—C26	119.60 (19)	C54—C49—S2	118.73 (17)
C23—C24—C25	121.81 (19)	C50—C49—S2	118.76 (18)
C23—C24—H16	119.1	C50—C55—H32	109.5
C25—C24—H16	119.1	C50—C55—H33	109.5
C27—C26—C25	120.8 (2)	H32—C55—H33	109.5
C27—C26—H17	119.6	C50—C55—H31	109.5
C25—C26—H17	119.6	H32—C55—H31	109.5
C26—C27—C28	119.6 (2)	H33—C55—H31	109.5
C26—C27—H18	120.2	S2—C56—H35	109.5
C28—C27—H18	120.2	S2—C56—H36	109.5
C29—C28—C27	121.2 (2)	H35—C56—H36	109.5
C29—C28—H19	119.4	S2—C56—H34	109.5
C27—C28—H19	119.4	H35—C56—H34	109.5
C28—C29—C30	120.6 (2)	H36—C56—H34	109.5
C28—C29—H20	119.7	C41—C46—C45	119.8 (2)
C30—C29—H20	119.7	C41—C46—H40	116.7 (18)
C32—C31—C40	118.38 (19)	C45—C46—H40	123.5 (18)
C32—C31—C21	118.96 (19)	C46—C41—C42	121.5 (2)
C40—C31—C21	122.66 (19)	C46—C41—S1	119.86 (16)
O4—C32—C31	123.66 (19)	C42—C41—S1	118.64 (17)
O4—C32—C33	114.94 (19)	C43—C42—C41	117.1 (2)
C31—C32—C33	121.4 (2)	C43—C42—C47	120.5 (2)
C34—C33—C32	120.6 (2)	C41—C42—C47	122.4 (2)
C34—C33—H21	119.7	C44—C43—C42	121.8 (2)
C32—C33—H21	119.7	C44—C43—H37	119.1
C33—C34—C35	120.7 (2)	C42—C43—H37	119.1
C33—C34—H22	119.6	C45—C44—C43	119.9 (2)
C35—C34—H22	119.6	C45—C44—H38	120
C36—C35—C34	122.0 (2)	C43—C44—H38	120
C36—C35—C40	119.3 (2)	C44—C45—C46	119.9 (2)
C34—C35—C40	118.7 (2)	C44—C45—H39	120.1
C39—C40—C35	117.8 (2)	C46—C45—H39	120.1
C39—C40—C31	122.1 (2)	C42—C47—H42	109.5
C35—C40—C31	120.1 (2)	C42—C47—H43	109.5
C38—C39—C40	121.2 (2)	H42—C47—H43	109.5
C38—C39—H26	119.4	C42—C47—H41	109.5
C40—C39—H26	119.4	H42—C47—H41	109.5
C39—C38—C37	120.8 (2)	H43—C47—H41	109.5
C39—C38—H25	119.6	S1—C48—H45	109.5
C37—C38—H25	119.6	S1—C48—H46	109.5
C36—C37—C38	119.3 (2)	H45—C48—H46	109.5
C36—C37—H24	120.3	S1—C48—H44	109.5
C38—C37—H24	120.3	H45—C48—H44	109.5
C37—C36—C35	121.5 (2)	H46—C48—H44	109.5
C20—C19—C18—C17	−2.6 (3)	C34—C35—C40—C39	−178.4 (2)
C15—C16—C17—C18	0.9 (3)	C36—C35—C40—C31	−177.65 (19)
C19—C18—C17—C16	1.3 (3)	C34—C35—C40—C31	2.5 (3)
C18—C19—C20—C15	1.8 (3)	C32—C31—C40—C39	−179.38 (19)
C18—C19—C20—C11	−177.12 (19)	C21—C31—C40—C39	1.0 (3)
C17—C16—C15—C14	176.37 (19)	C32—C31—C40—C35	−0.3 (3)
C17—C16—C15—C20	−1.7 (3)	C21—C31—C40—C35	−179.89 (18)
C19—C20—C15—C16	0.4 (3)	C35—C40—C39—C38	−1.3 (3)
C11—C20—C15—C16	179.30 (18)	C31—C40—C39—C38	177.8 (2)
C19—C20—C15—C14	−177.77 (17)	C40—C39—C38—C37	0.4 (4)
C11—C20—C15—C14	1.2 (3)	C39—C38—C37—C36	0.3 (4)
C16—C15—C14—C13	−176.40 (19)	C38—C37—C36—C35	−0.1 (4)
C20—C15—C14—C13	1.7 (3)	C34—C35—C36—C37	179.0 (2)
C15—C14—C13—C12	−2.0 (3)	C40—C35—C36—C37	−0.8 (3)
C15—C14—C13—C23	−179.65 (17)	C6—C7—C8—C9	−0.6 (4)
C14—C13—C12—O2	179.75 (18)	C7—C8—C9—C10	0.1 (4)
C23—C13—C12—O2	−2.6 (3)	C8—C9—C10—C5	−0.1 (3)
C14—C13—C12—C11	−0.6 (3)	C8—C9—C10—C1	180.0 (2)
C23—C13—C12—C11	177.01 (17)	C9—C10—C5—C6	0.6 (3)
O2—C12—C11—C20	−176.93 (17)	C1—C10—C5—C6	−179.46 (18)
C13—C12—C11—C20	3.4 (3)	C9—C10—C5—C4	−178.99 (19)
O2—C12—C11—C1	1.3 (3)	C1—C10—C5—C4	0.9 (3)
C13—C12—C11—C1	−178.31 (17)	C6—C5—C4—C3	−179.2 (2)
C19—C20—C11—C12	175.20 (18)	C10—C5—C4—C3	0.5 (3)
C15—C20—C11—C12	−3.7 (3)	C8—C7—C6—C5	1.2 (4)
C19—C20—C11—C1	−3.1 (3)	C4—C5—C6—C7	178.4 (2)
C15—C20—C11—C1	178.05 (17)	C10—C5—C6—C7	−1.2 (3)
C14—C13—C23—C24	69.0 (2)	C5—C4—C3—C2	−1.2 (3)
C12—C13—C23—C24	−108.6 (2)	C4—C3—C2—O1	−177.07 (18)
C14—C13—C23—C22	−111.3 (2)	C4—C3—C2—C1	0.5 (3)
C12—C13—C23—C22	71.0 (2)	O1—C2—C1—C10	178.28 (17)
C24—C23—C22—O3	−179.04 (17)	C3—C2—C1—C10	0.8 (3)
C13—C23—C22—O3	1.3 (3)	O1—C2—C1—C11	1.5 (3)
C24—C23—C22—C21	0.9 (3)	C3—C2—C1—C11	−175.94 (18)
C13—C23—C22—C21	−178.79 (17)	C9—C10—C1—C2	178.37 (19)
O3—C22—C21—C30	−179.71 (17)	C5—C10—C1—C2	−1.5 (3)
C23—C22—C21—C30	0.4 (3)	C9—C10—C1—C11	−4.9 (3)
O3—C22—C21—C31	−3.4 (3)	C5—C10—C1—C11	175.20 (17)
C23—C22—C21—C31	176.72 (18)	C12—C11—C1—C2	−88.3 (2)
C22—C21—C30—C25	−0.7 (3)	C20—C11—C1—C2	89.9 (2)
C31—C21—C30—C25	−176.95 (19)	C12—C11—C1—C10	95.0 (2)
C22—C21—C30—C29	178.07 (19)	C20—C11—C1—C10	−86.8 (2)
C31—C21—C30—C29	1.8 (3)	C50—C51—C52—C53	0.4 (4)
C29—C30—C25—C24	−179.02 (18)	C51—C52—C53—C54	1.5 (4)
C21—C30—C25—C24	−0.2 (3)	C49—C54—C53—C52	−1.1 (4)
C29—C30—C25—C26	−0.9 (3)	C52—C51—C50—C49	−2.6 (3)
C21—C30—C25—C26	177.88 (18)	C52—C51—C50—C55	175.5 (2)
C22—C23—C24—C25	−1.9 (3)	C53—C54—C49—C50	−1.2 (4)
C13—C23—C24—C25	177.83 (17)	C53—C54—C49—S2	179.4 (2)
C30—C25—C24—C23	1.5 (3)	C51—C50—C49—C54	3.0 (3)
C26—C25—C24—C23	−176.54 (19)	C55—C50—C49—C54	−175.1 (2)
C24—C25—C26—C27	177.4 (2)	C51—C50—C49—S2	−177.64 (17)
C30—C25—C26—C27	−0.6 (3)	C55—C50—C49—S2	4.3 (3)
C25—C26—C27—C28	1.6 (3)	O6—S2—C49—C54	7.7 (2)
C26—C27—C28—C29	−0.9 (3)	C56—S2—C49—C54	−99.5 (2)
C27—C28—C29—C30	−0.7 (3)	O6—S2—C49—C50	−171.73 (17)
C25—C30—C29—C28	1.6 (3)	C56—S2—C49—C50	81.1 (2)
C21—C30—C29—C28	−177.2 (2)	C45—C46—C41—C42	−2.2 (3)
C22—C21—C31—C32	−71.1 (3)	C45—C46—C41—S1	179.54 (18)
C30—C21—C31—C32	105.2 (2)	O5—S1—C41—C46	14.7 (2)
C22—C21—C31—C40	108.5 (2)	C48—S1—C41—C46	−93.9 (2)
C30—C21—C31—C40	−75.2 (3)	O5—S1—C41—C42	−163.65 (17)
C40—C31—C32—O4	176.95 (18)	C48—S1—C41—C42	87.8 (2)
C21—C31—C32—O4	−3.4 (3)	C46—C41—C42—C43	2.6 (3)
C40—C31—C32—C33	−2.1 (3)	S1—C41—C42—C43	−179.09 (18)
C21—C31—C32—C33	177.48 (18)	C46—C41—C42—C47	−176.5 (3)
O4—C32—C33—C34	−176.82 (19)	S1—C41—C42—C47	1.8 (3)
C31—C32—C33—C34	2.3 (3)	C41—C42—C43—C44	−1.1 (4)
C32—C33—C34—C35	0.0 (3)	C47—C42—C43—C44	178.0 (3)
C33—C34—C35—C36	177.8 (2)	C42—C43—C44—C45	−0.7 (4)
C33—C34—C35—C40	−2.4 (3)	C43—C44—C45—C46	1.2 (3)
C36—C35—C40—C39	1.5 (3)	C41—C46—C45—C44	0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.86 (4)	1.96 (3)	2.737 (2)	150 (3)
O2—H2···O6	0.84 (3)	2.03 (3)	2.767 (2)	147 (3)
O3—H3···O5	0.84 (3)	2.04 (3)	2.816 (2)	153 (2)
O4—H4···O6	0.87 (3)	2.08 (3)	2.896 (2)	155 (3)
C57—H47···O1	0.95 (3)	2.41 (3)	3.319 (3)	158 (2)
C46—H40···O1	0.93 (3)	2.23 (3)	3.151 (3)	175 (3)