A 1:2 co-crystal of 2,2′-thiodi­benzoic acid and tri­phenyl­phosphane oxide: crystal structure, Hirshfeld surface analysis and computational study

The asymmetric unit of the title co-crystal comprises two twisted mol­ecules of 2,2′-thiodi­benzoic acid and four mol­ecules of tri­phenyl­phosphane oxide. The three-dimensional mol­ecular packing is stabilized by hy­droxy-O—H...O(oxide) hydrogen bonds and TPPO-C—H...O(oxide, carbon­yl) and TDBA-C—H...(oxide, carbon­yl) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.092
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT112_ALERT_2_B ADDSYM Detects New (Pseudo) Symm. Elem         B         91 %Fit

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    P2       --C36      .        5.6 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C79 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       2.00 Check
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00020 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00010 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        426 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

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

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

2-[(2-Carboxyphenyl)sulfanyl]benzoic acid–(diphenylphosphoryl)benzene (1/2)

Crystal data

4C18H15OP·2C14H10O4S	F(000) = 3472
Mr = 1661.64	Dx = 1.324 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 10.7085 (1) Å	Cell parameters from 52739 reflections
b = 41.9751 (2) Å	θ = 4.2–75.9°
c = 18.9268 (1) Å	µ = 1.83 mm^−1
β = 101.490 (1)°	T = 100 K
V = 8336.92 (10) Å^3	Prism, colourless
Z = 4	0.17 × 0.16 × 0.09 mm

Data collection

XtaLAB Synergy, Dualflex, AtlasS2 diffractometer	17036 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	15740 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 5.2558 pixels mm^-1	θmax = 76.2°, θmin = 3.2°
ω scans	h = −13→13
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	k = −49→52
Tmin = 0.653, Tmax = 1.000	l = −23→23
94929 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 3.5049P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.003
17036 reflections	Δρmax = 0.42 e Å^−3
1079 parameters	Δρmin = −0.55 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
S1	0.86876 (3)	0.60239 (2)	0.45382 (2)	0.01933 (7)
O5	0.66647 (18)	0.68394 (3)	0.41031 (6)	0.0653 (5)
O6	0.63653 (11)	0.64495 (2)	0.48314 (5)	0.0298 (2)
H6O	0.644 (2)	0.6616 (5)	0.5178 (12)	0.064 (7)*
O7	1.05664 (8)	0.58755 (2)	0.57331 (5)	0.02348 (19)
O8	1.25159 (9)	0.57343 (2)	0.55791 (5)	0.0250 (2)
H8O	1.261 (2)	0.5646 (5)	0.6020 (12)	0.059 (6)*
C73	0.57062 (11)	0.63409 (3)	0.30175 (6)	0.0189 (2)
H73	0.510504	0.650346	0.296861	0.023*
C74	0.56910 (12)	0.61279 (3)	0.24561 (7)	0.0208 (2)
H74	0.507892	0.614647	0.203416	0.025*
C75	0.65935 (13)	0.58870 (3)	0.25272 (7)	0.0231 (3)
H75	0.659019	0.574453	0.215058	0.028*
C76	0.75002 (12)	0.58580 (3)	0.31576 (7)	0.0227 (3)
H76	0.809779	0.569467	0.320215	0.027*
C77	0.75263 (11)	0.60713 (3)	0.37271 (6)	0.0180 (2)
C78	0.66130 (11)	0.63139 (3)	0.36547 (6)	0.0161 (2)
C79	0.65763 (12)	0.65610 (3)	0.42226 (6)	0.0198 (2)
C80	1.01153 (11)	0.61285 (3)	0.42513 (6)	0.0167 (2)
C81	1.01083 (13)	0.62905 (3)	0.36024 (7)	0.0234 (3)
H81	0.933478	0.633723	0.329907	0.028*
C82	1.12341 (14)	0.63818 (4)	0.34059 (8)	0.0297 (3)
H82	1.120595	0.648892	0.297281	0.036*
C83	1.24037 (13)	0.63157 (4)	0.38468 (8)	0.0294 (3)
H83	1.315681	0.638162	0.371782	0.035*
C84	1.24298 (12)	0.61502 (3)	0.44811 (7)	0.0232 (3)
H84	1.321038	0.610079	0.477425	0.028*
C85	1.13031 (11)	0.60555 (3)	0.46905 (6)	0.0168 (2)
C86	1.14015 (11)	0.58810 (3)	0.53863 (6)	0.0170 (2)
S2	0.36308 (3)	0.60471 (2)	0.95618 (2)	0.01877 (7)
O9	0.56354 (8)	0.58971 (2)	1.06759 (4)	0.02008 (18)
O10	0.75481 (8)	0.57505 (2)	1.04690 (5)	0.02276 (19)
H10O	0.766 (2)	0.5668 (5)	1.0924 (12)	0.060 (6)*
O11	0.12548 (13)	0.68518 (2)	0.90397 (5)	0.0423 (3)
O12	0.15116 (10)	0.64745 (2)	0.98809 (5)	0.0254 (2)
H12O	0.1545 (18)	0.6638 (5)	1.0188 (11)	0.045 (5)*
C87	0.48876 (12)	0.62911 (3)	0.85303 (6)	0.0184 (2)
H87	0.408551	0.634762	0.827278	0.022*
C88	0.59558 (13)	0.63654 (3)	0.82546 (7)	0.0231 (3)
H88	0.586377	0.647289	0.781755	0.028*
C89	0.71638 (13)	0.62809 (3)	0.86246 (7)	0.0253 (3)
H89	0.787995	0.632986	0.843699	0.030*
C90	0.72868 (12)	0.61226 (3)	0.92771 (7)	0.0213 (2)
H90	0.809347	0.606453	0.952545	0.026*
C91	0.62200 (11)	0.60484 (3)	0.95702 (6)	0.0154 (2)
C92	0.49939 (11)	0.61319 (3)	0.91922 (6)	0.0151 (2)
C93	0.64177 (11)	0.58925 (3)	1.02911 (6)	0.0160 (2)
C94	0.24038 (11)	0.60750 (3)	0.87723 (6)	0.0179 (2)
C95	0.23738 (12)	0.58484 (3)	0.82279 (7)	0.0225 (3)
H95	0.297462	0.568554	0.828932	0.027*
C96	0.14576 (12)	0.58636 (3)	0.75969 (7)	0.0234 (3)
H96	0.145014	0.571214	0.723745	0.028*
C97	0.05526 (12)	0.61046 (3)	0.75020 (7)	0.0223 (3)
H97	−0.006374	0.611467	0.708014	0.027*
C98	0.05714 (11)	0.63302 (3)	0.80384 (6)	0.0194 (2)
H98	−0.003174	0.649254	0.797145	0.023*
C99	0.14835 (11)	0.63174 (3)	0.86788 (6)	0.0164 (2)
C100	0.14237 (11)	0.65763 (3)	0.92171 (6)	0.0181 (2)
P1	0.45306 (3)	0.53046 (2)	0.69428 (2)	0.01230 (6)
O1	0.32078 (8)	0.54411 (2)	0.67897 (4)	0.01763 (17)
C1	0.61145 (11)	0.53439 (3)	0.83070 (6)	0.0167 (2)
H1	0.656091	0.550177	0.811734	0.020*
C2	0.65061 (12)	0.52494 (3)	0.90237 (6)	0.0192 (2)
H2	0.721498	0.534351	0.931197	0.023*
C3	0.58344 (12)	0.50146 (3)	0.93049 (6)	0.0194 (2)
H3	0.610599	0.494813	0.977939	0.023*
C4	0.47584 (12)	0.48781 (3)	0.88817 (7)	0.0203 (2)
H4	0.430003	0.472469	0.907717	0.024*
C5	0.43666 (11)	0.49703 (3)	0.81683 (6)	0.0176 (2)
H5	0.364754	0.487840	0.788474	0.021*
C6	0.50568 (11)	0.52020 (3)	0.78760 (6)	0.0136 (2)
C7	0.53838 (12)	0.46861 (3)	0.66991 (7)	0.0198 (2)
H7	0.588550	0.469321	0.716034	0.024*
C8	0.54019 (13)	0.44169 (3)	0.62722 (8)	0.0254 (3)
H8	0.592086	0.424523	0.644795	0.030*
C9	0.46540 (14)	0.44035 (3)	0.55898 (8)	0.0306 (3)
H9	0.466881	0.422331	0.530569	0.037*
C10	0.38826 (17)	0.46583 (4)	0.53291 (8)	0.0403 (4)
H10	0.337265	0.464822	0.487039	0.048*
C11	0.38629 (15)	0.49291 (4)	0.57465 (7)	0.0312 (3)
H11	0.334659	0.510043	0.556555	0.037*
C12	0.46162 (11)	0.49447 (3)	0.64372 (6)	0.0160 (2)
C13	0.68681 (11)	0.54783 (3)	0.66017 (6)	0.0168 (2)
H13	0.710047	0.526522	0.666794	0.020*
C14	0.77099 (12)	0.56959 (3)	0.63990 (6)	0.0203 (2)
H14	0.850763	0.562941	0.633391	0.024*
C15	0.73532 (12)	0.60136 (3)	0.62942 (7)	0.0223 (3)
H15	0.790696	0.615862	0.614766	0.027*
C16	0.61775 (13)	0.61152 (3)	0.64067 (7)	0.0228 (3)
H16	0.595084	0.632870	0.634256	0.027*
C17	0.53354 (12)	0.58992 (3)	0.66151 (6)	0.0187 (2)
H17	0.454903	0.596820	0.669357	0.022*
C18	0.56734 (11)	0.55785 (3)	0.67064 (6)	0.0141 (2)
P2	−0.04151 (3)	0.53337 (2)	0.18925 (2)	0.01230 (6)
O2	−0.17363 (8)	0.54704 (2)	0.17137 (4)	0.01732 (17)
C19	0.11406 (11)	0.53774 (3)	0.32684 (6)	0.0167 (2)
H19	0.160010	0.553259	0.307909	0.020*
C20	0.15104 (12)	0.52863 (3)	0.39889 (6)	0.0194 (2)
H20	0.221743	0.538005	0.427976	0.023*
C21	0.08202 (12)	0.50557 (3)	0.42697 (6)	0.0205 (2)
H21	0.107516	0.499240	0.474765	0.025*
C22	−0.02503 (12)	0.49184 (3)	0.38417 (7)	0.0211 (2)
H22	−0.071898	0.476702	0.403634	0.025*
C23	−0.06198 (11)	0.50071 (3)	0.31239 (6)	0.0176 (2)
H23	−0.133366	0.491457	0.283687	0.021*
C24	0.00844 (11)	0.52362 (3)	0.28324 (6)	0.0139 (2)
C25	0.04771 (12)	0.47170 (3)	0.16729 (6)	0.0187 (2)
H25	0.099716	0.473162	0.212801	0.022*
C26	0.04960 (12)	0.44426 (3)	0.12632 (7)	0.0226 (3)
H26	0.103258	0.427486	0.144451	0.027*
C27	−0.02776 (13)	0.44180 (3)	0.05889 (7)	0.0257 (3)
H27	−0.025983	0.423458	0.031542	0.031*
C28	−0.10793 (15)	0.46669 (4)	0.03213 (8)	0.0345 (3)
H28	−0.160726	0.464959	−0.013102	0.041*
C29	−0.11000 (14)	0.49422 (3)	0.07241 (7)	0.0280 (3)
H29	−0.163834	0.510912	0.053961	0.034*
C30	−0.03175 (11)	0.49697 (3)	0.14038 (6)	0.0151 (2)
C31	0.03988 (12)	0.59295 (3)	0.15930 (7)	0.0192 (2)
H31	−0.039378	0.599663	0.166545	0.023*
C32	0.12523 (13)	0.61484 (3)	0.14071 (7)	0.0234 (3)
H32	0.102725	0.636236	0.135335	0.028*
C33	0.24365 (12)	0.60499 (3)	0.13014 (7)	0.0212 (3)
H33	0.299701	0.619741	0.117004	0.025*
C34	0.27898 (11)	0.57320 (3)	0.13908 (6)	0.0193 (2)
H34	0.359108	0.566710	0.132823	0.023*
C35	0.19411 (11)	0.55108 (3)	0.15742 (6)	0.0161 (2)
H35	0.217465	0.529756	0.163287	0.019*
C36	0.07374 (11)	0.56081 (3)	0.16705 (6)	0.0142 (2)
P3	0.09805 (3)	0.71259 (2)	0.12227 (2)	0.01599 (7)
O3	0.17981 (8)	0.69166 (2)	0.08605 (5)	0.02155 (18)
C37	−0.08417 (12)	0.68424 (3)	0.19179 (7)	0.0244 (3)
H37	−0.030988	0.688982	0.235659	0.029*
C38	−0.19660 (13)	0.66742 (3)	0.19036 (8)	0.0315 (3)
H38	−0.218007	0.660839	0.233340	0.038*
C39	−0.27655 (13)	0.66046 (3)	0.12557 (9)	0.0312 (3)
H39	−0.351472	0.649149	0.124875	0.037*
C40	−0.24498 (14)	0.67032 (3)	0.06181 (8)	0.0323 (3)
H40	−0.299242	0.665798	0.018164	0.039*
C41	−0.13297 (14)	0.68691 (3)	0.06245 (7)	0.0274 (3)
H41	−0.112158	0.693373	0.019234	0.033*
C42	−0.05124 (12)	0.69397 (3)	0.12764 (7)	0.0185 (2)
C43	−0.03715 (12)	0.76945 (3)	0.08915 (8)	0.0248 (3)
H43	−0.081000	0.764003	0.125165	0.030*
C44	−0.06608 (13)	0.79759 (3)	0.05104 (8)	0.0299 (3)
H44	−0.128479	0.811110	0.061853	0.036*
C45	−0.00170 (14)	0.80552 (3)	−0.00327 (8)	0.0316 (3)
H45	−0.021237	0.824361	−0.028957	0.038*
C46	0.09146 (14)	0.78551 (3)	−0.01936 (8)	0.0305 (3)
H46	0.134234	0.790946	−0.055853	0.037*
C47	0.12140 (12)	0.75730 (3)	0.01881 (7)	0.0239 (3)
H47	0.183816	0.743850	0.007752	0.029*
C48	0.05757 (12)	0.74923 (3)	0.07371 (7)	0.0193 (2)
C49	0.29856 (12)	0.70791 (3)	0.23785 (7)	0.0233 (3)
H49	0.334641	0.694746	0.207831	0.028*
C50	0.36378 (13)	0.71402 (3)	0.30779 (8)	0.0293 (3)
H50	0.443912	0.705170	0.324258	0.035*
C51	0.30930 (14)	0.73330 (3)	0.35291 (8)	0.0312 (3)
H51	0.352266	0.736994	0.399933	0.037*
C52	0.19116 (14)	0.74706 (3)	0.32820 (8)	0.0308 (3)
H52	0.155341	0.760138	0.358497	0.037*
C53	0.12620 (13)	0.74136 (3)	0.25837 (7)	0.0253 (3)
H53	0.047151	0.750767	0.241795	0.030*
C54	0.17919 (12)	0.72151 (3)	0.21276 (7)	0.0188 (2)
P4	0.59434 (3)	0.71241 (2)	0.62054 (2)	0.01558 (7)
O4	0.65852 (8)	0.68597 (2)	0.58832 (4)	0.01947 (18)
C55	0.36994 (13)	0.67928 (3)	0.59742 (8)	0.0282 (3)
H55	0.389594	0.674863	0.552729	0.034*
C56	0.26067 (15)	0.66662 (4)	0.61513 (9)	0.0361 (3)
H56	0.206716	0.653874	0.582208	0.043*
C57	0.23188 (14)	0.67296 (4)	0.68190 (9)	0.0357 (3)
H57	0.158804	0.664312	0.693791	0.043*
C58	0.31085 (14)	0.69200 (4)	0.73083 (8)	0.0324 (3)
H58	0.290945	0.696173	0.775564	0.039*
C59	0.42035 (13)	0.70500 (3)	0.71334 (7)	0.0248 (3)
H59	0.473371	0.717929	0.746290	0.030*
C60	0.45058 (12)	0.69863 (3)	0.64644 (7)	0.0190 (2)
C61	0.77928 (13)	0.70565 (3)	0.74264 (7)	0.0256 (3)
H61	0.789190	0.685356	0.724829	0.031*
C62	0.85001 (14)	0.71467 (4)	0.80939 (8)	0.0328 (3)
H62	0.907827	0.700498	0.835864	0.039*
C63	0.83457 (14)	0.74466 (4)	0.83647 (7)	0.0310 (3)
H63	0.880548	0.750466	0.881635	0.037*
C64	0.75106 (15)	0.76599 (4)	0.79662 (8)	0.0351 (3)
H64	0.741536	0.786242	0.814744	0.042*
C65	0.68114 (14)	0.75731 (3)	0.72948 (8)	0.0313 (3)
H65	0.625732	0.771861	0.702523	0.038*
C66	0.69371 (11)	0.72688 (3)	0.70238 (7)	0.0191 (2)
C67	0.45982 (12)	0.76745 (3)	0.56674 (7)	0.0231 (3)
H67	0.417547	0.765712	0.604988	0.028*
C68	0.43043 (13)	0.79226 (3)	0.51757 (8)	0.0275 (3)
H68	0.369387	0.807282	0.523296	0.033*
C69	0.49220 (13)	0.79458 (3)	0.46002 (8)	0.0283 (3)
H69	0.472196	0.811139	0.427055	0.034*
C70	0.58383 (13)	0.77230 (3)	0.45135 (7)	0.0261 (3)
H70	0.624512	0.773921	0.412430	0.031*
C71	0.61497 (12)	0.74760 (3)	0.50053 (7)	0.0207 (2)
H71	0.676790	0.732791	0.494812	0.025*
C72	0.55292 (11)	0.74510 (3)	0.55873 (7)	0.0183 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01503 (14)	0.02690 (16)	0.01590 (14)	0.00414 (11)	0.00267 (11)	0.00504 (11)
O5	0.1541 (15)	0.0195 (5)	0.0287 (6)	−0.0136 (7)	0.0334 (8)	−0.0030 (4)
O6	0.0519 (6)	0.0196 (5)	0.0228 (5)	−0.0019 (4)	0.0189 (4)	−0.0022 (4)
O7	0.0198 (4)	0.0312 (5)	0.0197 (4)	0.0043 (4)	0.0047 (3)	0.0069 (4)
O8	0.0187 (4)	0.0351 (5)	0.0200 (4)	0.0091 (4)	0.0011 (3)	0.0089 (4)
C73	0.0162 (5)	0.0211 (6)	0.0188 (6)	0.0022 (5)	0.0022 (4)	0.0008 (5)
C74	0.0175 (6)	0.0274 (6)	0.0164 (6)	−0.0040 (5)	0.0004 (4)	−0.0018 (5)
C75	0.0251 (6)	0.0255 (6)	0.0194 (6)	−0.0024 (5)	0.0065 (5)	−0.0073 (5)
C76	0.0211 (6)	0.0232 (6)	0.0249 (6)	0.0056 (5)	0.0072 (5)	−0.0028 (5)
C77	0.0162 (5)	0.0206 (6)	0.0170 (5)	0.0017 (5)	0.0028 (4)	0.0014 (5)
C78	0.0160 (5)	0.0161 (5)	0.0164 (5)	0.0000 (4)	0.0037 (4)	0.0006 (4)
C79	0.0234 (6)	0.0185 (6)	0.0165 (6)	0.0024 (5)	0.0018 (5)	0.0007 (5)
C80	0.0186 (6)	0.0154 (5)	0.0164 (5)	0.0031 (4)	0.0042 (4)	0.0003 (4)
C81	0.0235 (6)	0.0277 (7)	0.0192 (6)	0.0062 (5)	0.0046 (5)	0.0069 (5)
C82	0.0310 (7)	0.0344 (7)	0.0262 (7)	0.0060 (6)	0.0116 (6)	0.0128 (6)
C83	0.0246 (7)	0.0337 (7)	0.0334 (7)	0.0006 (6)	0.0139 (6)	0.0093 (6)
C84	0.0177 (6)	0.0260 (6)	0.0260 (6)	0.0022 (5)	0.0044 (5)	0.0043 (5)
C85	0.0190 (6)	0.0149 (5)	0.0165 (5)	0.0018 (4)	0.0037 (4)	0.0003 (4)
C86	0.0165 (5)	0.0161 (5)	0.0168 (5)	0.0009 (4)	−0.0005 (4)	−0.0003 (4)
S2	0.01312 (13)	0.02878 (16)	0.01450 (13)	0.00328 (11)	0.00294 (10)	0.00385 (11)
O9	0.0180 (4)	0.0253 (4)	0.0169 (4)	0.0024 (3)	0.0033 (3)	0.0036 (3)
O10	0.0172 (4)	0.0317 (5)	0.0182 (4)	0.0088 (4)	0.0007 (3)	0.0046 (4)
O11	0.0794 (9)	0.0169 (5)	0.0236 (5)	−0.0017 (5)	−0.0069 (5)	0.0018 (4)
O12	0.0420 (6)	0.0184 (4)	0.0189 (4)	0.0065 (4)	0.0136 (4)	0.0013 (4)
C87	0.0184 (6)	0.0192 (6)	0.0168 (5)	0.0033 (5)	0.0016 (4)	0.0022 (4)
C88	0.0278 (7)	0.0233 (6)	0.0196 (6)	0.0017 (5)	0.0083 (5)	0.0060 (5)
C89	0.0212 (6)	0.0294 (7)	0.0281 (7)	0.0002 (5)	0.0118 (5)	0.0054 (5)
C90	0.0159 (6)	0.0238 (6)	0.0246 (6)	0.0019 (5)	0.0050 (5)	0.0021 (5)
C91	0.0152 (5)	0.0150 (5)	0.0157 (5)	0.0013 (4)	0.0027 (4)	−0.0007 (4)
C92	0.0166 (5)	0.0137 (5)	0.0152 (5)	0.0014 (4)	0.0037 (4)	−0.0008 (4)
C93	0.0154 (5)	0.0150 (5)	0.0162 (5)	0.0005 (4)	−0.0003 (4)	−0.0012 (4)
C94	0.0138 (5)	0.0237 (6)	0.0167 (5)	−0.0001 (5)	0.0037 (4)	0.0023 (5)
C95	0.0187 (6)	0.0264 (6)	0.0236 (6)	0.0027 (5)	0.0073 (5)	−0.0017 (5)
C96	0.0227 (6)	0.0292 (7)	0.0193 (6)	−0.0042 (5)	0.0063 (5)	−0.0050 (5)
C97	0.0177 (6)	0.0309 (7)	0.0167 (6)	−0.0058 (5)	−0.0003 (5)	−0.0003 (5)
C98	0.0151 (5)	0.0234 (6)	0.0193 (6)	−0.0011 (5)	0.0024 (5)	0.0035 (5)
C99	0.0142 (5)	0.0186 (6)	0.0166 (5)	−0.0027 (4)	0.0036 (4)	0.0027 (4)
C100	0.0155 (5)	0.0191 (6)	0.0179 (6)	−0.0015 (4)	−0.0007 (4)	0.0024 (5)
P1	0.01150 (13)	0.01351 (13)	0.01110 (13)	0.00026 (10)	0.00034 (10)	0.00070 (10)
O1	0.0128 (4)	0.0217 (4)	0.0176 (4)	0.0025 (3)	0.0013 (3)	0.0031 (3)
C1	0.0172 (6)	0.0182 (5)	0.0144 (5)	−0.0027 (4)	0.0023 (4)	−0.0004 (4)
C2	0.0172 (6)	0.0259 (6)	0.0133 (5)	−0.0021 (5)	−0.0001 (4)	−0.0022 (5)
C3	0.0210 (6)	0.0254 (6)	0.0120 (5)	0.0037 (5)	0.0035 (4)	0.0022 (5)
C4	0.0228 (6)	0.0210 (6)	0.0180 (6)	−0.0027 (5)	0.0062 (5)	0.0037 (5)
C5	0.0172 (5)	0.0188 (6)	0.0161 (5)	−0.0027 (5)	0.0014 (4)	−0.0002 (4)
C6	0.0146 (5)	0.0137 (5)	0.0125 (5)	0.0017 (4)	0.0024 (4)	−0.0003 (4)
C7	0.0202 (6)	0.0193 (6)	0.0196 (6)	0.0003 (5)	0.0030 (5)	−0.0023 (5)
C8	0.0257 (7)	0.0180 (6)	0.0349 (7)	−0.0006 (5)	0.0118 (6)	−0.0047 (5)
C9	0.0329 (7)	0.0278 (7)	0.0336 (7)	−0.0083 (6)	0.0124 (6)	−0.0168 (6)
C10	0.0489 (10)	0.0429 (9)	0.0232 (7)	0.0014 (7)	−0.0069 (7)	−0.0169 (6)
C11	0.0382 (8)	0.0311 (7)	0.0190 (6)	0.0060 (6)	−0.0069 (6)	−0.0056 (5)
C12	0.0155 (5)	0.0173 (5)	0.0149 (5)	−0.0032 (4)	0.0026 (4)	−0.0016 (4)
C13	0.0167 (5)	0.0175 (5)	0.0153 (5)	0.0000 (4)	0.0015 (4)	−0.0014 (4)
C14	0.0156 (5)	0.0280 (6)	0.0172 (6)	−0.0037 (5)	0.0032 (4)	−0.0022 (5)
C15	0.0227 (6)	0.0253 (6)	0.0175 (6)	−0.0089 (5)	0.0009 (5)	0.0035 (5)
C16	0.0272 (7)	0.0166 (6)	0.0232 (6)	−0.0022 (5)	0.0016 (5)	0.0043 (5)
C17	0.0186 (6)	0.0174 (6)	0.0195 (6)	0.0016 (5)	0.0024 (5)	0.0015 (4)
C18	0.0155 (5)	0.0162 (5)	0.0096 (5)	−0.0013 (4)	0.0000 (4)	0.0002 (4)
P2	0.01140 (13)	0.01358 (13)	0.01122 (13)	0.00096 (10)	0.00054 (10)	0.00039 (10)
O2	0.0131 (4)	0.0211 (4)	0.0170 (4)	0.0036 (3)	0.0013 (3)	0.0014 (3)
C19	0.0175 (6)	0.0175 (5)	0.0151 (5)	−0.0020 (4)	0.0028 (4)	−0.0006 (4)
C20	0.0178 (6)	0.0253 (6)	0.0136 (5)	−0.0021 (5)	−0.0002 (4)	−0.0030 (5)
C21	0.0222 (6)	0.0265 (6)	0.0126 (5)	0.0023 (5)	0.0031 (5)	0.0018 (5)
C22	0.0235 (6)	0.0232 (6)	0.0171 (6)	−0.0031 (5)	0.0058 (5)	0.0032 (5)
C23	0.0169 (5)	0.0193 (6)	0.0159 (5)	−0.0023 (5)	0.0019 (4)	−0.0003 (4)
C24	0.0148 (5)	0.0140 (5)	0.0129 (5)	0.0023 (4)	0.0027 (4)	−0.0005 (4)
C25	0.0184 (6)	0.0192 (6)	0.0176 (6)	0.0011 (5)	0.0013 (5)	−0.0015 (5)
C26	0.0228 (6)	0.0175 (6)	0.0288 (7)	0.0017 (5)	0.0085 (5)	−0.0025 (5)
C27	0.0255 (7)	0.0243 (6)	0.0288 (7)	−0.0048 (5)	0.0093 (5)	−0.0125 (5)
C28	0.0375 (8)	0.0377 (8)	0.0231 (7)	0.0042 (7)	−0.0066 (6)	−0.0143 (6)
C29	0.0323 (7)	0.0288 (7)	0.0183 (6)	0.0086 (6)	−0.0062 (5)	−0.0050 (5)
C30	0.0142 (5)	0.0166 (5)	0.0146 (5)	−0.0010 (4)	0.0030 (4)	−0.0014 (4)
C31	0.0189 (6)	0.0175 (6)	0.0215 (6)	0.0031 (5)	0.0046 (5)	0.0019 (5)
C32	0.0275 (7)	0.0154 (6)	0.0273 (6)	0.0013 (5)	0.0051 (5)	0.0048 (5)
C33	0.0218 (6)	0.0221 (6)	0.0189 (6)	−0.0056 (5)	0.0020 (5)	0.0043 (5)
C34	0.0155 (5)	0.0247 (6)	0.0176 (6)	−0.0018 (5)	0.0027 (4)	−0.0016 (5)
C35	0.0169 (6)	0.0154 (5)	0.0153 (5)	0.0010 (4)	0.0012 (4)	−0.0010 (4)
C36	0.0157 (5)	0.0158 (5)	0.0101 (5)	0.0001 (4)	0.0002 (4)	−0.0002 (4)
P3	0.01686 (14)	0.01392 (14)	0.01790 (14)	0.00187 (11)	0.00514 (11)	−0.00059 (11)
O3	0.0249 (4)	0.0197 (4)	0.0215 (4)	0.0058 (4)	0.0082 (4)	−0.0020 (3)
C37	0.0198 (6)	0.0265 (6)	0.0257 (6)	−0.0007 (5)	0.0020 (5)	0.0058 (5)
C38	0.0247 (7)	0.0321 (7)	0.0380 (8)	−0.0025 (6)	0.0066 (6)	0.0114 (6)
C39	0.0210 (6)	0.0197 (6)	0.0507 (9)	−0.0035 (5)	0.0018 (6)	0.0018 (6)
C40	0.0296 (7)	0.0229 (7)	0.0390 (8)	−0.0050 (6)	−0.0060 (6)	−0.0052 (6)
C41	0.0332 (7)	0.0230 (6)	0.0245 (6)	−0.0046 (6)	0.0020 (5)	−0.0029 (5)
C42	0.0184 (6)	0.0124 (5)	0.0241 (6)	0.0016 (4)	0.0032 (5)	−0.0001 (4)
C43	0.0209 (6)	0.0217 (6)	0.0337 (7)	0.0023 (5)	0.0102 (5)	0.0037 (5)
C44	0.0231 (6)	0.0202 (6)	0.0472 (8)	0.0053 (5)	0.0085 (6)	0.0047 (6)
C45	0.0305 (7)	0.0203 (6)	0.0432 (8)	0.0004 (6)	0.0054 (6)	0.0114 (6)
C46	0.0315 (7)	0.0281 (7)	0.0339 (7)	−0.0005 (6)	0.0109 (6)	0.0091 (6)
C47	0.0231 (6)	0.0227 (6)	0.0273 (6)	0.0015 (5)	0.0083 (5)	0.0032 (5)
C48	0.0182 (6)	0.0162 (6)	0.0234 (6)	−0.0002 (5)	0.0039 (5)	0.0014 (5)
C49	0.0202 (6)	0.0230 (6)	0.0270 (7)	0.0017 (5)	0.0051 (5)	−0.0018 (5)
C50	0.0215 (6)	0.0308 (7)	0.0325 (7)	0.0011 (5)	−0.0021 (5)	0.0002 (6)
C51	0.0353 (8)	0.0301 (7)	0.0249 (7)	−0.0059 (6)	−0.0019 (6)	−0.0052 (6)
C52	0.0379 (8)	0.0267 (7)	0.0279 (7)	0.0008 (6)	0.0065 (6)	−0.0095 (6)
C53	0.0257 (6)	0.0234 (6)	0.0266 (7)	0.0039 (5)	0.0046 (5)	−0.0051 (5)
C54	0.0185 (6)	0.0165 (5)	0.0215 (6)	−0.0015 (5)	0.0040 (5)	−0.0014 (5)
P4	0.01651 (14)	0.01290 (14)	0.01749 (14)	0.00079 (11)	0.00375 (11)	−0.00068 (11)
O4	0.0241 (4)	0.0156 (4)	0.0196 (4)	0.0037 (3)	0.0063 (3)	−0.0012 (3)
C55	0.0279 (7)	0.0244 (7)	0.0328 (7)	−0.0063 (5)	0.0073 (6)	−0.0046 (5)
C56	0.0295 (7)	0.0259 (7)	0.0530 (9)	−0.0089 (6)	0.0084 (7)	−0.0013 (7)
C57	0.0253 (7)	0.0294 (7)	0.0562 (10)	0.0005 (6)	0.0170 (7)	0.0153 (7)
C58	0.0294 (7)	0.0373 (8)	0.0344 (7)	0.0095 (6)	0.0157 (6)	0.0123 (6)
C59	0.0236 (6)	0.0267 (7)	0.0251 (6)	0.0043 (5)	0.0071 (5)	0.0026 (5)
C60	0.0193 (6)	0.0143 (5)	0.0239 (6)	0.0025 (5)	0.0055 (5)	0.0036 (5)
C61	0.0236 (6)	0.0248 (6)	0.0268 (7)	0.0015 (5)	0.0015 (5)	−0.0020 (5)
C62	0.0287 (7)	0.0372 (8)	0.0288 (7)	0.0001 (6)	−0.0033 (6)	0.0010 (6)
C63	0.0282 (7)	0.0435 (8)	0.0216 (6)	−0.0135 (6)	0.0058 (5)	−0.0076 (6)
C64	0.0381 (8)	0.0325 (8)	0.0342 (8)	−0.0052 (6)	0.0061 (6)	−0.0163 (6)
C65	0.0340 (7)	0.0241 (7)	0.0330 (7)	0.0036 (6)	0.0001 (6)	−0.0085 (6)
C66	0.0173 (6)	0.0205 (6)	0.0202 (6)	−0.0024 (5)	0.0050 (5)	−0.0025 (5)
C67	0.0192 (6)	0.0202 (6)	0.0309 (7)	0.0021 (5)	0.0072 (5)	0.0029 (5)
C68	0.0197 (6)	0.0213 (6)	0.0414 (8)	0.0045 (5)	0.0056 (6)	0.0067 (6)
C69	0.0258 (7)	0.0227 (6)	0.0352 (7)	0.0012 (5)	0.0028 (6)	0.0117 (6)
C70	0.0260 (7)	0.0248 (6)	0.0282 (7)	−0.0024 (5)	0.0074 (5)	0.0056 (5)
C71	0.0189 (6)	0.0181 (6)	0.0255 (6)	−0.0010 (5)	0.0052 (5)	0.0006 (5)
C72	0.0164 (6)	0.0153 (5)	0.0226 (6)	−0.0020 (4)	0.0024 (5)	0.0009 (5)

Geometric parameters (Å, º)

S1—C77	1.7839 (12)	C20—H20	0.9300
S1—C80	1.7764 (12)	C20—C21	1.3866 (18)
O5—C79	1.1978 (17)	C21—H21	0.9300
O6—H6O	0.95 (2)	C21—C22	1.3902 (18)
O6—C79	1.3043 (15)	C22—H22	0.9300
O7—C86	1.2104 (15)	C22—C23	1.3880 (17)
O8—H8O	0.90 (2)	C23—H23	0.9300
O8—C86	1.3279 (15)	C23—C24	1.4015 (16)
C73—H73	0.9300	C25—H25	0.9300
C73—C74	1.3862 (17)	C25—C26	1.3910 (17)
C73—C78	1.3942 (17)	C25—C30	1.3914 (17)
C74—H74	0.9300	C26—H26	0.9300
C74—C75	1.3866 (19)	C26—C27	1.3799 (19)
C75—H75	0.9300	C27—H27	0.9300
C75—C76	1.3854 (19)	C27—C28	1.383 (2)
C76—H76	0.9300	C28—H28	0.9300
C76—C77	1.3975 (17)	C28—C29	1.3871 (19)
C77—C78	1.3996 (16)	C29—H29	0.9300
C78—C79	1.4998 (16)	C29—C30	1.3933 (17)
C80—C81	1.4024 (16)	C31—H31	0.9300
C80—C85	1.4077 (17)	C31—C32	1.3898 (18)
C81—H81	0.9300	C31—C36	1.3969 (16)
C81—C82	1.3847 (19)	C32—H32	0.9300
C82—H82	0.9300	C32—C33	1.3857 (19)
C82—C83	1.388 (2)	C33—H33	0.9300
C83—H83	0.9300	C33—C34	1.3883 (18)
C83—C84	1.3826 (18)	C34—H34	0.9300
C84—H84	0.9300	C34—C35	1.3907 (17)
C84—C85	1.4004 (17)	C35—H35	0.9300
C85—C86	1.4921 (16)	C35—C36	1.3983 (16)
S2—C92	1.7760 (12)	P3—O3	1.4991 (9)
S2—C94	1.7863 (12)	P3—C42	1.8004 (13)
O9—C93	1.2147 (15)	P3—C48	1.8001 (12)
O10—H10O	0.91 (2)	P3—C54	1.7989 (13)
O10—C93	1.3309 (14)	C37—H37	0.9300
O11—C100	1.2075 (16)	C37—C38	1.3912 (19)
O12—H12O	0.89 (2)	C37—C42	1.3915 (17)
O12—C100	1.3126 (15)	C38—H38	0.9300
C87—H87	0.9300	C38—C39	1.380 (2)
C87—C88	1.3842 (17)	C39—H39	0.9300
C87—C92	1.4042 (16)	C39—C40	1.380 (2)
C88—H88	0.9300	C40—H40	0.9300
C88—C89	1.3887 (19)	C40—C41	1.385 (2)
C89—H89	0.9300	C41—H41	0.9300
C89—C90	1.3853 (18)	C41—C42	1.3949 (18)
C90—H90	0.9300	C43—H43	0.9300
C90—C91	1.4008 (16)	C43—C44	1.3865 (19)
C91—C92	1.4087 (16)	C43—C48	1.3973 (17)
C91—C93	1.4900 (16)	C44—H44	0.9300
C94—C95	1.3980 (17)	C44—C45	1.388 (2)
C94—C99	1.4031 (17)	C45—H45	0.9300
C95—H95	0.9300	C45—C46	1.384 (2)
C95—C96	1.3879 (18)	C46—H46	0.9300
C96—H96	0.9300	C46—C47	1.3911 (18)
C96—C97	1.3876 (19)	C47—H47	0.9300
C97—H97	0.9300	C47—C48	1.3943 (17)
C97—C98	1.3856 (18)	C49—H49	0.9300
C98—H98	0.9300	C49—C50	1.3919 (19)
C98—C99	1.3979 (16)	C49—C54	1.3941 (18)
C99—C100	1.4997 (17)	C50—H50	0.9300
P1—O1	1.5018 (8)	C50—C51	1.387 (2)
P1—C6	1.7961 (11)	C51—H51	0.9300
P1—C12	1.8003 (12)	C51—C52	1.385 (2)
P1—C18	1.7994 (12)	C52—H52	0.9300
C1—H1	0.9300	C52—C53	1.3863 (19)
C1—C2	1.3952 (16)	C53—H53	0.9300
C1—C6	1.3909 (16)	C53—C54	1.3987 (17)
C2—H2	0.9300	P4—O4	1.4975 (8)
C2—C3	1.3874 (18)	P4—C60	1.8014 (13)
C3—H3	0.9300	P4—C66	1.8010 (13)
C3—C4	1.3890 (18)	P4—C72	1.8005 (12)
C4—H4	0.9300	C55—H55	0.9300
C4—C5	1.3868 (17)	C55—C56	1.386 (2)
C5—H5	0.9300	C55—C60	1.3955 (18)
C5—C6	1.4007 (16)	C56—H56	0.9300
C7—H7	0.9300	C56—C57	1.385 (2)
C7—C8	1.3915 (17)	C57—H57	0.9300
C7—C12	1.3920 (17)	C57—C58	1.378 (2)
C8—H8	0.9300	C58—H58	0.9300
C8—C9	1.379 (2)	C58—C59	1.3917 (19)
C9—H9	0.9300	C59—H59	0.9300
C9—C10	1.381 (2)	C59—C60	1.3937 (18)
C10—H10	0.9300	C61—H61	0.9300
C10—C11	1.387 (2)	C61—C62	1.3899 (19)
C11—H11	0.9300	C61—C66	1.3915 (18)
C11—C12	1.3941 (17)	C62—H62	0.9300
C13—H13	0.9300	C62—C63	1.381 (2)
C13—C14	1.3901 (17)	C63—H63	0.9300
C13—C18	1.3979 (16)	C63—C64	1.379 (2)
C14—H14	0.9300	C64—H64	0.9300
C14—C15	1.3902 (18)	C64—C65	1.389 (2)
C15—H15	0.9300	C65—H65	0.9300
C15—C16	1.3854 (19)	C65—C66	1.3929 (18)
C16—H16	0.9300	C67—H67	0.9300
C16—C17	1.3902 (17)	C67—C68	1.3902 (18)
C17—H17	0.9300	C67—C72	1.3991 (17)
C17—C18	1.3956 (16)	C68—H68	0.9300
P2—O2	1.5014 (8)	C68—C69	1.386 (2)
P2—C24	1.7997 (11)	C69—H69	0.9300
P2—C30	1.7998 (12)	C69—C70	1.389 (2)
P2—C36	1.7980 (12)	C70—H70	0.9300
C19—H19	0.9300	C70—C71	1.3889 (18)
C19—C20	1.3956 (16)	C71—H71	0.9300
C19—C24	1.3927 (16)	C71—C72	1.3990 (17)
C80—S1—C77	101.78 (6)	C21—C22—H22	120.0
C79—O6—H6O	109.8 (14)	C23—C22—C21	120.02 (11)
C86—O8—H8O	111.7 (14)	C23—C22—H22	120.0
C74—C73—H73	119.7	C22—C23—H23	120.0
C74—C73—C78	120.70 (11)	C22—C23—C24	119.91 (11)
C78—C73—H73	119.7	C24—C23—H23	120.0
C73—C74—H74	120.2	C19—C24—P2	122.36 (9)
C73—C74—C75	119.62 (11)	C19—C24—C23	119.73 (10)
C75—C74—H74	120.2	C23—C24—P2	117.90 (9)
C74—C75—H75	119.9	C26—C25—H25	119.9
C76—C75—C74	120.21 (11)	C26—C25—C30	120.21 (11)
C76—C75—H75	119.9	C30—C25—H25	119.9
C75—C76—H76	119.6	C25—C26—H26	119.8
C75—C76—C77	120.71 (12)	C27—C26—C25	120.31 (12)
C77—C76—H76	119.6	C27—C26—H26	119.8
C76—C77—S1	119.72 (9)	C26—C27—H27	120.1
C76—C77—C78	118.98 (11)	C26—C27—C28	119.79 (12)
C78—C77—S1	121.28 (9)	C28—C27—H27	120.1
C73—C78—C77	119.77 (11)	C27—C28—H28	119.8
C73—C78—C79	116.79 (11)	C27—C28—C29	120.33 (13)
C77—C78—C79	123.40 (11)	C29—C28—H28	119.8
O5—C79—O6	123.45 (12)	C28—C29—H29	119.9
O5—C79—C78	121.67 (12)	C28—C29—C30	120.27 (13)
O6—C79—C78	114.76 (11)	C30—C29—H29	119.9
C81—C80—S1	122.19 (9)	C25—C30—P2	123.58 (9)
C81—C80—C85	117.98 (11)	C25—C30—C29	119.09 (11)
C85—C80—S1	119.81 (9)	C29—C30—P2	117.33 (9)
C80—C81—H81	119.5	C32—C31—H31	120.2
C82—C81—C80	121.10 (12)	C32—C31—C36	119.67 (11)
C82—C81—H81	119.5	C36—C31—H31	120.2
C81—C82—H82	119.6	C31—C32—H32	119.8
C81—C82—C83	120.85 (12)	C33—C32—C31	120.40 (12)
C83—C82—H82	119.6	C33—C32—H32	119.8
C82—C83—H83	120.6	C32—C33—H33	119.9
C84—C83—C82	118.84 (12)	C32—C33—C34	120.29 (11)
C84—C83—H83	120.6	C34—C33—H33	119.9
C83—C84—H84	119.4	C33—C34—H34	120.1
C83—C84—C85	121.26 (12)	C33—C34—C35	119.76 (11)
C85—C84—H84	119.4	C35—C34—H34	120.1
C80—C85—C86	121.64 (11)	C34—C35—H35	119.9
C84—C85—C80	119.94 (11)	C34—C35—C36	120.18 (11)
C84—C85—C86	118.41 (11)	C36—C35—H35	119.9
O7—C86—O8	124.24 (11)	C31—C36—P2	117.85 (9)
O7—C86—C85	123.93 (11)	C31—C36—C35	119.68 (11)
O8—C86—C85	111.83 (10)	C35—C36—P2	122.46 (9)
C92—S2—C94	100.52 (5)	O3—P3—C42	112.18 (5)
C93—O10—H10O	110.6 (14)	O3—P3—C48	111.75 (5)
C100—O12—H12O	111.0 (12)	O3—P3—C54	110.01 (6)
C88—C87—H87	119.4	C48—P3—C42	105.87 (6)
C88—C87—C92	121.16 (11)	C54—P3—C42	107.61 (6)
C92—C87—H87	119.4	C54—P3—C48	109.24 (6)
C87—C88—H88	119.7	C38—C37—H37	120.0
C87—C88—C89	120.59 (11)	C38—C37—C42	120.05 (13)
C89—C88—H88	119.7	C42—C37—H37	120.0
C88—C89—H89	120.5	C37—C38—H38	119.8
C90—C89—C88	119.06 (12)	C39—C38—C37	120.41 (13)
C90—C89—H89	120.5	C39—C38—H38	119.8
C89—C90—H90	119.4	C38—C39—H39	120.1
C89—C90—C91	121.30 (12)	C38—C39—C40	119.79 (13)
C91—C90—H90	119.4	C40—C39—H39	120.1
C90—C91—C92	119.64 (11)	C39—C40—H40	119.8
C90—C91—C93	118.82 (11)	C39—C40—C41	120.39 (13)
C92—C91—C93	121.50 (10)	C41—C40—H40	119.8
C87—C92—S2	121.33 (9)	C40—C41—H41	119.9
C87—C92—C91	118.24 (11)	C40—C41—C42	120.28 (13)
C91—C92—S2	120.40 (9)	C42—C41—H41	119.9
O9—C93—O10	123.83 (11)	C37—C42—P3	123.98 (10)
O9—C93—C91	123.56 (11)	C37—C42—C41	119.08 (12)
O10—C93—C91	112.61 (10)	C41—C42—P3	116.74 (10)
C95—C94—S2	118.49 (9)	C44—C43—H43	119.8
C95—C94—C99	119.21 (11)	C44—C43—C48	120.32 (12)
C99—C94—S2	122.30 (9)	C48—C43—H43	119.8
C94—C95—H95	119.6	C43—C44—H44	120.1
C96—C95—C94	120.76 (12)	C43—C44—C45	119.82 (13)
C96—C95—H95	119.6	C45—C44—H44	120.1
C95—C96—H96	120.0	C44—C45—H45	119.9
C97—C96—C95	120.05 (12)	C46—C45—C44	120.25 (13)
C97—C96—H96	120.0	C46—C45—H45	119.9
C96—C97—H97	120.1	C45—C46—H46	119.9
C98—C97—C96	119.71 (12)	C45—C46—C47	120.28 (13)
C98—C97—H97	120.1	C47—C46—H46	119.9
C97—C98—H98	119.5	C46—C47—H47	120.1
C97—C98—C99	120.98 (12)	C46—C47—C48	119.82 (12)
C99—C98—H98	119.5	C48—C47—H47	120.1
C94—C99—C100	124.32 (11)	C43—C48—P3	121.55 (10)
C98—C99—C94	119.28 (11)	C47—C48—P3	118.94 (9)
C98—C99—C100	116.38 (11)	C47—C48—C43	119.50 (12)
O11—C100—O12	123.80 (12)	C50—C49—H49	120.0
O11—C100—C99	121.95 (11)	C50—C49—C54	120.05 (12)
O12—C100—C99	114.18 (10)	C54—C49—H49	120.0
O1—P1—C6	112.35 (5)	C49—C50—H50	120.0
O1—P1—C12	111.32 (5)	C51—C50—C49	120.01 (13)
O1—P1—C18	111.73 (5)	C51—C50—H50	120.0
C6—P1—C12	106.40 (5)	C50—C51—H51	119.9
C6—P1—C18	107.57 (5)	C52—C51—C50	120.25 (13)
C18—P1—C12	107.14 (5)	C52—C51—H51	119.9
C2—C1—H1	120.0	C51—C52—H52	120.0
C6—C1—H1	120.0	C51—C52—C53	120.08 (13)
C6—C1—C2	120.03 (11)	C53—C52—H52	120.0
C1—C2—H2	120.1	C52—C53—H53	119.9
C3—C2—C1	119.77 (11)	C52—C53—C54	120.19 (13)
C3—C2—H2	120.1	C54—C53—H53	119.9
C2—C3—H3	119.8	C49—C54—P3	118.37 (9)
C2—C3—C4	120.38 (11)	C49—C54—C53	119.40 (12)
C4—C3—H3	119.8	C53—C54—P3	122.23 (10)
C3—C4—H4	119.9	O4—P4—C60	111.07 (5)
C5—C4—C3	120.12 (11)	O4—P4—C66	111.08 (5)
C5—C4—H4	119.9	O4—P4—C72	111.95 (5)
C4—C5—H5	120.1	C66—P4—C60	105.35 (6)
C4—C5—C6	119.81 (11)	C72—P4—C60	107.95 (6)
C6—C5—H5	120.1	C72—P4—C66	109.19 (6)
C1—C6—P1	122.24 (9)	C56—C55—H55	119.9
C1—C6—C5	119.86 (10)	C56—C55—C60	120.19 (13)
C5—C6—P1	117.90 (9)	C60—C55—H55	119.9
C8—C7—H7	119.9	C55—C56—H56	120.0
C8—C7—C12	120.14 (12)	C57—C56—C55	119.95 (14)
C12—C7—H7	119.9	C57—C56—H56	120.0
C7—C8—H8	119.9	C56—C57—H57	119.8
C9—C8—C7	120.28 (13)	C58—C57—C56	120.41 (13)
C9—C8—H8	119.9	C58—C57—H57	119.8
C8—C9—H9	120.1	C57—C58—H58	120.0
C8—C9—C10	119.85 (12)	C57—C58—C59	120.05 (14)
C10—C9—H9	120.1	C59—C58—H58	120.0
C9—C10—H10	119.8	C58—C59—H59	120.0
C9—C10—C11	120.47 (13)	C58—C59—C60	120.01 (13)
C11—C10—H10	119.8	C60—C59—H59	120.0
C10—C11—H11	120.0	C55—C60—P4	117.07 (10)
C10—C11—C12	120.08 (13)	C59—C60—P4	123.46 (10)
C12—C11—H11	120.0	C59—C60—C55	119.39 (12)
C7—C12—P1	123.65 (9)	C62—C61—H61	119.9
C7—C12—C11	119.17 (11)	C62—C61—C66	120.23 (13)
C11—C12—P1	117.18 (10)	C66—C61—H61	119.9
C14—C13—H13	119.9	C61—C62—H62	119.9
C14—C13—C18	120.22 (11)	C63—C62—C61	120.12 (14)
C18—C13—H13	119.9	C63—C62—H62	119.9
C13—C14—H14	120.2	C62—C63—H63	120.0
C13—C14—C15	119.66 (12)	C64—C63—C62	120.07 (13)
C15—C14—H14	120.2	C64—C63—H63	120.0
C14—C15—H15	119.8	C63—C64—H64	119.9
C16—C15—C14	120.38 (12)	C63—C64—C65	120.19 (13)
C16—C15—H15	119.8	C65—C64—H64	119.9
C15—C16—H16	119.9	C64—C65—H65	119.9
C15—C16—C17	120.22 (12)	C64—C65—C66	120.23 (14)
C17—C16—H16	119.9	C66—C65—H65	119.9
C16—C17—H17	120.1	C61—C66—P4	117.83 (10)
C16—C17—C18	119.82 (11)	C61—C66—C65	119.14 (12)
C18—C17—H17	120.1	C65—C66—P4	122.83 (10)
C13—C18—P1	121.99 (9)	C68—C67—H67	120.0
C17—C18—P1	118.34 (9)	C68—C67—C72	120.06 (12)
C17—C18—C13	119.66 (11)	C72—C67—H67	120.0
O2—P2—C24	113.00 (5)	C67—C68—H68	120.0
O2—P2—C30	110.92 (5)	C69—C68—C67	119.93 (12)
O2—P2—C36	111.25 (5)	C69—C68—H68	120.0
C24—P2—C30	106.18 (5)	C68—C69—H69	119.8
C36—P2—C24	107.09 (5)	C68—C69—C70	120.30 (12)
C36—P2—C30	108.12 (5)	C70—C69—H69	119.8
C20—C19—H19	120.0	C69—C70—H70	119.9
C24—C19—H19	120.0	C69—C70—C71	120.30 (12)
C24—C19—C20	120.09 (11)	C71—C70—H70	119.9
C19—C20—H20	120.1	C70—C71—H71	120.2
C21—C20—C19	119.78 (11)	C70—C71—C72	119.70 (12)
C21—C20—H20	120.1	C72—C71—H71	120.2
C20—C21—H21	119.8	C67—C72—P4	121.96 (10)
C20—C21—C22	120.45 (11)	C67—C72—C71	119.70 (11)
C22—C21—H21	119.8	C71—C72—P4	118.33 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6O···O4	0.95 (2)	1.66 (2)	2.6070 (12)	171 (2)
O8—H8O···O1^i	0.90 (2)	1.70 (2)	2.5763 (12)	163 (2)
O10—H10O···O2^ii	0.91 (2)	1.72 (2)	2.6077 (12)	163 (2)
O12—H12O···O3^iii	0.90 (2)	1.71 (2)	2.5978 (12)	170.9 (19)
C16—H16···O4	0.93	2.53	3.3333 (15)	144
C44—H44···O4^iv	0.93	2.43	3.2404 (17)	145
C52—H52···O11^v	0.93	2.49	3.3231 (16)	149
C62—H62···O11^i	0.93	2.51	3.367 (2)	153
C64—H64···O5^vi	0.93	2.46	3.263 (2)	144
C68—H68···O3^vi	0.93	2.55	3.2747 (17)	135
C71—H71···O5	0.93	2.59	3.2765 (18)	131
C75—H75···O2^i	0.93	2.41	3.1184 (16)	133
C96—H96···O1	0.93	2.49	3.1832 (15)	132

Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1; (iii) x, y, z+1; (iv) x−1, −y+1/2, z−3/2; (v) x, −y+1/2, z−3/2; (vi) x, −y+1/2, z−1/2.