4,6-Bis(diphenyl-phosphan-yl)-2,8-di-methyl-phenoxathiin dichloro-methane monosolvate.

The title compound, C(38)H(30)OP(2)S·CH(2)Cl(2), belongs to the xanthene family of ligands containing S- and O-donor atoms in the central heterocylic ring. Positions 2 and 8 on the xanthene backbone are functionalized with methyl groups to allow for the selective functionalization of the backbone at positions 4 and 6 with diphenyl-phosphanyl units. The title compound shows a significant 'roof-like' bending along the axis of planarity involving the O- and S-donor atoms and the benzene rings, resulting in a dihedral angle between the mean planes of the benzene rings of 32.88 (13)°.

Related literature

For a closely related compound, see: Goertz et al. (1998 ▶). For complexation to metal centre and catalysis, see: Kranenburg et al. (1995 ▶). For related P-donor ligands, see: Marimuthu et al. (2008 ▶). For a related structure, see: Hillebrand et al. (1995 ▶).

Experimental

Crystal data

C38H30OP2S·CH2Cl2

M = 681.55

Monoclinic,

a = 9.3605 (7) Å

b = 20.6796 (15) Å

c = 18.1360 (15) Å

β = 104.955 (1)°

V = 3391.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 173 K

0.47 × 0.36 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer

46059 measured reflections

8183 independent reflections

6527 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.07

8183 reflections

408 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009920/fj2525sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009920/fj2525Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009920/fj2525Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C38H30OP2S·CH2Cl2	F(000) = 1416
Mr = 681.55	Dx = 1.335 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9922 reflections
a = 9.3605 (7) Å	θ = 2.3–28.3°
b = 20.6796 (15) Å	µ = 0.38 mm−1
c = 18.1360 (15) Å	T = 173 K
β = 104.955 (1)°	Prism, colourless
V = 3391.7 (5) Å3	0.47 × 0.36 × 0.28 mm
Z = 4

Bruker APEXII CCD diffractometer	6527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 28.0°, θmin = 1.5°
φ and ω scans	h = −12→12
46059 measured reflections	k = −27→27
8183 independent reflections	l = −15→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.4429P] where P = (Fo2 + 2Fc2)/3
8183 reflections	(Δ/σ)max = 0.001
408 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.67489 (15)	−0.01794 (7)	0.12353 (8)	0.0246 (3)
C2	0.61337 (16)	−0.07280 (7)	0.08142 (8)	0.0275 (3)
H2	0.6780	−0.1031	0.0675	0.033*
C3	0.46158 (16)	−0.08469 (7)	0.05916 (8)	0.0282 (3)
C4	0.36781 (16)	−0.04140 (7)	0.08135 (8)	0.0274 (3)
H4	0.2641	−0.0486	0.0671	0.033*
C5	0.42542 (15)	0.01272 (7)	0.12445 (8)	0.0245 (3)
C6	0.57712 (15)	0.02502 (7)	0.14406 (8)	0.0234 (3)
C7	0.63835 (15)	0.19416 (7)	0.18215 (8)	0.0240 (3)
C8	0.55781 (16)	0.25217 (7)	0.17171 (8)	0.0272 (3)
H8	0.6101	0.2920	0.1770	0.033*
C9	0.40319 (16)	0.25350 (7)	0.15383 (9)	0.0295 (3)
C10	0.32755 (16)	0.19526 (7)	0.14747 (9)	0.0302 (3)
H10	0.2225	0.1952	0.1351	0.036*
C11	0.40387 (16)	0.13687 (7)	0.15907 (8)	0.0260 (3)
C12	0.55822 (15)	0.13654 (7)	0.17502 (7)	0.0233 (3)
C13	0.39974 (19)	−0.14374 (8)	0.01255 (10)	0.0377 (4)
H13A	0.3703	−0.1759	0.0455	0.057*
H13B	0.4754	−0.1623	−0.0097	0.057*
H13C	0.3134	−0.1313	−0.0284	0.057*
C14	0.31804 (19)	0.31613 (8)	0.14184 (11)	0.0410 (4)
H14A	0.2463	0.3155	0.0918	0.062*
H14B	0.3867	0.3523	0.1441	0.062*
H14C	0.2657	0.3213	0.1818	0.062*
C21	0.93204 (15)	−0.01030 (7)	0.25149 (8)	0.0249 (3)
C22	0.83985 (17)	−0.03259 (8)	0.29494 (9)	0.0319 (3)
H22	0.7394	−0.0424	0.2710	0.038*
C23	0.89407 (18)	−0.04055 (9)	0.37329 (9)	0.0376 (4)
H23	0.8297	−0.0556	0.4024	0.045*
C24	1.04062 (18)	−0.02698 (8)	0.40987 (9)	0.0353 (4)
H24	1.0763	−0.0326	0.4635	0.042*
C25	1.13368 (18)	−0.00517 (8)	0.36723 (10)	0.0362 (4)
H25	1.2345	0.0038	0.3913	0.043*
C26	1.07971 (17)	0.00357 (8)	0.28947 (9)	0.0328 (3)
H26	1.1442	0.0194	0.2609	0.039*
C31	0.94616 (16)	−0.07369 (7)	0.11622 (9)	0.0270 (3)
C32	0.9978 (2)	−0.12632 (8)	0.16371 (10)	0.0425 (4)
H32	0.9980	−0.1242	0.2161	0.051*
C33	1.0489 (2)	−0.18156 (9)	0.13569 (12)	0.0523 (5)
H33	1.0840	−0.2169	0.1688	0.063*
C34	1.0487 (2)	−0.18526 (9)	0.05995 (11)	0.0451 (4)
H34	1.0836	−0.2232	0.0408	0.054*
C35	0.99786 (18)	−0.13374 (8)	0.01163 (9)	0.0372 (4)
H35	0.9971	−0.1365	−0.0408	0.045*
C36	0.94815 (16)	−0.07838 (8)	0.03957 (9)	0.0308 (3)
H36	0.9148	−0.0429	0.0062	0.037*
C41	0.89248 (15)	0.27288 (7)	0.18795 (8)	0.0268 (3)
C42	0.86834 (18)	0.29087 (8)	0.11127 (9)	0.0360 (4)
H42	0.8192	0.2619	0.0723	0.043*
C43	0.91518 (19)	0.35028 (9)	0.09168 (11)	0.0425 (4)
H43	0.8969	0.3622	0.0395	0.051*
C44	0.98901 (19)	0.39268 (8)	0.14815 (11)	0.0428 (4)
H44	1.0223	0.4333	0.1346	0.051*
C45	1.0138 (2)	0.37585 (8)	0.22366 (11)	0.0429 (4)
H45	1.0639	0.4050	0.2622	0.051*
C46	0.96594 (18)	0.31636 (8)	0.24391 (10)	0.0343 (3)
H46	0.9834	0.3052	0.2963	0.041*
C51	0.88289 (17)	0.19002 (7)	0.31191 (9)	0.0297 (3)
C52	0.7990 (2)	0.22244 (9)	0.35306 (10)	0.0415 (4)
H52	0.7145	0.2464	0.3270	0.050*
C53	0.8384 (2)	0.21988 (11)	0.43235 (11)	0.0525 (5)
H53	0.7803	0.2421	0.4601	0.063*
C54	0.9611 (3)	0.18540 (10)	0.47112 (11)	0.0568 (6)
H54	0.9873	0.1839	0.5253	0.068*
C55	1.0442 (3)	0.15360 (10)	0.43126 (12)	0.0649 (6)
H55	1.1289	0.1299	0.4577	0.078*
C56	1.0059 (2)	0.15565 (9)	0.35211 (11)	0.0495 (5)
H56	1.0647	0.1332	0.3250	0.059*
O1	0.63781 (10)	0.07871 (4)	0.18809 (6)	0.0254 (2)
P1	0.87456 (4)	0.001195 (17)	0.14751 (2)	0.02475 (9)
P2	0.84253 (4)	0.189890 (18)	0.20739 (2)	0.02557 (9)
S1	0.30570 (4)	0.064058 (19)	0.15779 (2)	0.03050 (10)
C57	0.5549 (3)	0.08998 (11)	0.36408 (12)	0.0588 (5)
H57A	0.5305	0.0567	0.3235	0.071*
H57B	0.6410	0.1149	0.3574	0.071*
Cl1	0.40384 (9)	0.14207 (3)	0.35502 (3)	0.07616 (19)
Cl2	0.60096 (7)	0.05229 (3)	0.45321 (3)	0.06801 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0241 (7)	0.0248 (7)	0.0251 (7)	−0.0002 (5)	0.0067 (5)	0.0043 (5)
C2	0.0296 (7)	0.0257 (7)	0.0280 (7)	−0.0009 (6)	0.0091 (6)	0.0003 (6)
C3	0.0308 (7)	0.0282 (7)	0.0247 (7)	−0.0043 (6)	0.0057 (6)	0.0014 (6)
C4	0.0249 (7)	0.0309 (7)	0.0253 (7)	−0.0040 (6)	0.0047 (6)	0.0032 (6)
C5	0.0248 (7)	0.0258 (7)	0.0227 (7)	0.0007 (5)	0.0059 (5)	0.0038 (5)
C6	0.0251 (7)	0.0229 (7)	0.0214 (6)	−0.0011 (5)	0.0045 (5)	0.0027 (5)
C7	0.0238 (7)	0.0282 (7)	0.0198 (6)	0.0004 (6)	0.0052 (5)	−0.0020 (5)
C8	0.0293 (7)	0.0249 (7)	0.0272 (7)	0.0013 (6)	0.0068 (6)	−0.0024 (6)
C9	0.0291 (7)	0.0298 (7)	0.0293 (8)	0.0061 (6)	0.0070 (6)	−0.0013 (6)
C10	0.0233 (7)	0.0352 (8)	0.0322 (8)	0.0030 (6)	0.0075 (6)	−0.0019 (6)
C11	0.0244 (7)	0.0295 (7)	0.0246 (7)	−0.0011 (6)	0.0074 (6)	−0.0007 (6)
C12	0.0246 (7)	0.0260 (7)	0.0191 (6)	0.0031 (5)	0.0051 (5)	0.0008 (5)
C13	0.0369 (9)	0.0360 (9)	0.0406 (9)	−0.0076 (7)	0.0107 (7)	−0.0098 (7)
C14	0.0365 (9)	0.0333 (9)	0.0520 (11)	0.0091 (7)	0.0092 (8)	−0.0033 (7)
C21	0.0251 (7)	0.0226 (7)	0.0275 (7)	−0.0001 (5)	0.0077 (6)	0.0006 (5)
C22	0.0248 (7)	0.0389 (8)	0.0326 (8)	−0.0013 (6)	0.0083 (6)	0.0037 (7)
C23	0.0347 (8)	0.0482 (10)	0.0329 (8)	0.0002 (7)	0.0143 (7)	0.0074 (7)
C24	0.0381 (8)	0.0388 (9)	0.0275 (8)	0.0037 (7)	0.0056 (7)	0.0012 (7)
C25	0.0290 (8)	0.0400 (9)	0.0366 (9)	−0.0044 (7)	0.0028 (7)	−0.0006 (7)
C26	0.0278 (7)	0.0366 (8)	0.0344 (8)	−0.0057 (6)	0.0090 (6)	0.0021 (7)
C31	0.0239 (7)	0.0295 (7)	0.0295 (7)	−0.0012 (6)	0.0100 (6)	0.0010 (6)
C32	0.0623 (12)	0.0354 (9)	0.0346 (9)	0.0130 (8)	0.0213 (8)	0.0060 (7)
C33	0.0747 (14)	0.0362 (10)	0.0512 (11)	0.0197 (9)	0.0256 (10)	0.0075 (8)
C34	0.0497 (11)	0.0378 (9)	0.0529 (11)	0.0042 (8)	0.0222 (9)	−0.0104 (8)
C35	0.0331 (8)	0.0480 (10)	0.0332 (8)	−0.0062 (7)	0.0133 (7)	−0.0104 (7)
C36	0.0262 (7)	0.0366 (8)	0.0295 (8)	−0.0028 (6)	0.0070 (6)	0.0014 (6)
C41	0.0230 (7)	0.0286 (7)	0.0307 (8)	0.0013 (6)	0.0103 (6)	−0.0018 (6)
C42	0.0326 (8)	0.0440 (9)	0.0329 (8)	−0.0032 (7)	0.0109 (7)	0.0005 (7)
C43	0.0360 (9)	0.0503 (10)	0.0437 (10)	0.0030 (8)	0.0146 (8)	0.0166 (8)
C44	0.0377 (9)	0.0320 (8)	0.0648 (12)	0.0037 (7)	0.0244 (9)	0.0092 (8)
C45	0.0466 (10)	0.0309 (8)	0.0563 (11)	−0.0075 (7)	0.0224 (9)	−0.0110 (8)
C46	0.0391 (9)	0.0325 (8)	0.0340 (8)	−0.0034 (7)	0.0141 (7)	−0.0045 (6)
C51	0.0310 (7)	0.0262 (7)	0.0288 (7)	−0.0041 (6)	0.0022 (6)	0.0022 (6)
C52	0.0394 (9)	0.0540 (11)	0.0308 (8)	−0.0005 (8)	0.0084 (7)	0.0023 (8)
C53	0.0611 (12)	0.0645 (13)	0.0334 (10)	−0.0123 (10)	0.0150 (9)	−0.0037 (9)
C54	0.0847 (16)	0.0486 (11)	0.0274 (9)	−0.0151 (11)	−0.0030 (9)	0.0046 (8)
C55	0.0803 (16)	0.0536 (12)	0.0421 (11)	0.0176 (11)	−0.0182 (11)	0.0022 (10)
C56	0.0538 (11)	0.0435 (10)	0.0405 (10)	0.0141 (9)	−0.0069 (8)	−0.0034 (8)
O1	0.0243 (5)	0.0226 (5)	0.0271 (5)	0.0010 (4)	0.0027 (4)	−0.0005 (4)
P1	0.02381 (18)	0.02421 (18)	0.02701 (19)	−0.00075 (14)	0.00797 (14)	0.00316 (14)
P2	0.02309 (18)	0.02554 (19)	0.02756 (19)	0.00042 (14)	0.00558 (14)	−0.00296 (14)
S1	0.02473 (18)	0.0316 (2)	0.0379 (2)	−0.00240 (14)	0.01310 (15)	−0.00110 (16)
C57	0.0696 (14)	0.0653 (13)	0.0483 (12)	−0.0136 (11)	0.0277 (11)	0.0025 (10)
Cl1	0.1172 (6)	0.0525 (3)	0.0529 (3)	0.0151 (3)	0.0113 (3)	0.0040 (2)
Cl2	0.0751 (4)	0.0842 (4)	0.0416 (3)	0.0195 (3)	0.0094 (3)	0.0037 (3)

C1—C6	1.393 (2)	C26—H26	0.9500
C1—C2	1.405 (2)	C31—C32	1.395 (2)
C1—P1	1.8492 (14)	C31—C36	1.399 (2)
C2—C3	1.395 (2)	C31—P1	1.8345 (15)
C2—H2	0.9500	C32—C33	1.384 (2)
C3—C4	1.384 (2)	C32—H32	0.9500
C3—C13	1.513 (2)	C33—C34	1.375 (3)
C4—C5	1.392 (2)	C33—H33	0.9500
C4—H4	0.9500	C34—C35	1.384 (3)
C5—C6	1.3953 (19)	C34—H34	0.9500
C5—S1	1.7601 (14)	C35—C36	1.380 (2)
C6—O1	1.3996 (16)	C35—H35	0.9500
C7—C12	1.3961 (19)	C36—H36	0.9500
C7—C8	1.4035 (19)	C41—C46	1.397 (2)
C7—P2	1.8489 (14)	C41—C42	1.400 (2)
C8—C9	1.399 (2)	C41—P2	1.8367 (15)
C8—H8	0.9500	C42—C43	1.381 (2)
C9—C10	1.387 (2)	C42—H42	0.9500
C9—C14	1.507 (2)	C43—C44	1.389 (3)
C10—C11	1.391 (2)	C43—H43	0.9500
C10—H10	0.9500	C44—C45	1.373 (3)
C11—C12	1.3983 (19)	C44—H44	0.9500
C11—S1	1.7610 (15)	C45—C46	1.391 (2)
C12—O1	1.3966 (16)	C45—H45	0.9500
C13—H13A	0.9800	C46—H46	0.9500
C13—H13B	0.9800	C51—C52	1.387 (2)
C13—H13C	0.9800	C51—C56	1.389 (2)
C14—H14A	0.9800	C51—P2	1.8349 (16)
C14—H14B	0.9800	C52—C53	1.390 (2)
C14—H14C	0.9800	C52—H52	0.9500
C21—C22	1.389 (2)	C53—C54	1.380 (3)
C21—C26	1.406 (2)	C53—H53	0.9500
C21—P1	1.8381 (15)	C54—C55	1.360 (3)
C22—C23	1.390 (2)	C54—H54	0.9500
C22—H22	0.9500	C55—C56	1.387 (3)
C23—C24	1.390 (2)	C55—H55	0.9500
C23—H23	0.9500	C56—H56	0.9500
C24—C25	1.381 (2)	C57—Cl2	1.745 (2)
C24—H24	0.9500	C57—Cl1	1.751 (2)
C25—C26	1.382 (2)	C57—H57A	0.9900
C25—H25	0.9500	C57—H57B	0.9900
C6—C1—C2	117.04 (13)	C32—C31—P1	124.33 (12)
C6—C1—P1	119.63 (11)	C36—C31—P1	117.76 (11)
C2—C1—P1	123.24 (11)	C33—C32—C31	120.99 (16)
C3—C2—C1	122.92 (13)	C33—C32—H32	119.5
C3—C2—H2	118.5	C31—C32—H32	119.5
C1—C2—H2	118.5	C34—C33—C32	120.07 (17)
C4—C3—C2	118.47 (13)	C34—C33—H33	120.0
C4—C3—C13	120.31 (14)	C32—C33—H33	120.0
C2—C3—C13	121.22 (14)	C33—C34—C35	120.08 (16)
C3—C4—C5	120.04 (13)	C33—C34—H34	120.0
C3—C4—H4	120.0	C35—C34—H34	120.0
C5—C4—H4	120.0	C36—C35—C34	119.97 (15)
C4—C5—C6	120.73 (13)	C36—C35—H35	120.0
C4—C5—S1	119.29 (11)	C34—C35—H35	120.0
C6—C5—S1	119.92 (11)	C35—C36—C31	120.98 (15)
C1—C6—C5	120.74 (13)	C35—C36—H36	119.5
C1—C6—O1	117.41 (12)	C31—C36—H36	119.5
C5—C6—O1	121.77 (12)	C46—C41—C42	118.26 (14)
C12—C7—C8	117.39 (13)	C46—C41—P2	124.34 (12)
C12—C7—P2	118.59 (10)	C42—C41—P2	117.07 (12)
C8—C7—P2	124.00 (11)	C43—C42—C41	120.73 (16)
C9—C8—C7	122.37 (14)	C43—C42—H42	119.6
C9—C8—H8	118.8	C41—C42—H42	119.6
C7—C8—H8	118.8	C42—C43—C44	120.15 (16)
C10—C9—C8	118.53 (13)	C42—C43—H43	119.9
C10—C9—C14	119.65 (14)	C44—C43—H43	119.9
C8—C9—C14	121.81 (14)	C45—C44—C43	119.93 (16)
C9—C10—C11	120.66 (13)	C45—C44—H44	120.0
C9—C10—H10	119.7	C43—C44—H44	120.0
C11—C10—H10	119.7	C44—C45—C46	120.29 (16)
C10—C11—C12	119.89 (13)	C44—C45—H45	119.9
C10—C11—S1	119.63 (11)	C46—C45—H45	119.9
C12—C11—S1	120.42 (11)	C45—C46—C41	120.62 (16)
C7—C12—O1	117.70 (12)	C45—C46—H46	119.7
C7—C12—C11	121.12 (13)	C41—C46—H46	119.7
O1—C12—C11	121.11 (12)	C52—C51—C56	118.19 (16)
C3—C13—H13A	109.5	C52—C51—P2	124.20 (12)
C3—C13—H13B	109.5	C56—C51—P2	117.61 (13)
H13A—C13—H13B	109.5	C51—C52—C53	120.12 (18)
C3—C13—H13C	109.5	C51—C52—H52	119.9
H13A—C13—H13C	109.5	C53—C52—H52	119.9
H13B—C13—H13C	109.5	C54—C53—C52	120.7 (2)
C9—C14—H14A	109.5	C54—C53—H53	119.7
C9—C14—H14B	109.5	C52—C53—H53	119.7
H14A—C14—H14B	109.5	C55—C54—C53	119.59 (18)
C9—C14—H14C	109.5	C55—C54—H54	120.2
H14A—C14—H14C	109.5	C53—C54—H54	120.2
H14B—C14—H14C	109.5	C54—C55—C56	120.28 (19)
C22—C21—C26	117.78 (14)	C54—C55—H55	119.9
C22—C21—P1	124.39 (11)	C56—C55—H55	119.9
C26—C21—P1	117.83 (11)	C55—C56—C51	121.12 (19)
C21—C22—C23	120.19 (14)	C55—C56—H56	119.4
C21—C22—H22	119.9	C51—C56—H56	119.4
C23—C22—H22	119.9	C12—O1—C6	117.53 (10)
C24—C23—C22	121.29 (15)	C31—P1—C21	100.06 (7)
C24—C23—H23	119.4	C31—P1—C1	100.04 (6)
C22—C23—H23	119.4	C21—P1—C1	102.95 (6)
C25—C24—C23	119.08 (15)	C51—P2—C41	101.66 (7)
C25—C24—H24	120.5	C51—P2—C7	100.36 (7)
C23—C24—H24	120.5	C41—P2—C7	101.89 (6)
C24—C25—C26	119.79 (15)	C5—S1—C11	98.28 (7)
C24—C25—H25	120.1	Cl2—C57—Cl1	111.22 (11)
C26—C25—H25	120.1	Cl2—C57—H57A	109.4
C25—C26—C21	121.85 (14)	Cl1—C57—H57A	109.4
C25—C26—H26	119.1	Cl2—C57—H57B	109.4
C21—C26—H26	119.1	Cl1—C57—H57B	109.4
C32—C31—C36	117.91 (14)	H57A—C57—H57B	108.0
C6—C1—C2—C3	1.0 (2)	C46—C41—C42—C43	−0.4 (2)
P1—C1—C2—C3	−175.58 (11)	P2—C41—C42—C43	−174.05 (13)
C1—C2—C3—C4	−1.8 (2)	C41—C42—C43—C44	0.9 (2)
C1—C2—C3—C13	178.82 (14)	C42—C43—C44—C45	−0.8 (3)
C2—C3—C4—C5	0.4 (2)	C43—C44—C45—C46	0.3 (3)
C13—C3—C4—C5	179.78 (14)	C44—C45—C46—C41	0.2 (3)
C3—C4—C5—C6	1.7 (2)	C42—C41—C46—C45	−0.1 (2)
C3—C4—C5—S1	−175.53 (11)	P2—C41—C46—C45	173.01 (13)
C2—C1—C6—C5	1.2 (2)	C56—C51—C52—C53	−0.2 (3)
P1—C1—C6—C5	177.91 (10)	P2—C51—C52—C53	−179.86 (14)
C2—C1—C6—O1	178.01 (12)	C51—C52—C53—C54	0.2 (3)
P1—C1—C6—O1	−5.27 (17)	C52—C53—C54—C55	0.0 (3)
C4—C5—C6—C1	−2.6 (2)	C53—C54—C55—C56	−0.1 (3)
S1—C5—C6—C1	174.68 (11)	C54—C55—C56—C51	0.1 (3)
C4—C5—C6—O1	−179.26 (12)	C52—C51—C56—C55	0.0 (3)
S1—C5—C6—O1	−2.00 (18)	P2—C51—C56—C55	179.73 (17)
C12—C7—C8—C9	−0.8 (2)	C7—C12—O1—C6	−145.15 (12)
P2—C7—C8—C9	−178.94 (11)	C11—C12—O1—C6	37.94 (17)
C7—C8—C9—C10	1.0 (2)	C1—C6—O1—C12	145.19 (12)
C7—C8—C9—C14	−179.24 (14)	C5—C6—O1—C12	−38.02 (17)
C8—C9—C10—C11	0.4 (2)	C32—C31—P1—C21	11.81 (16)
C14—C9—C10—C11	−179.35 (14)	C36—C31—P1—C21	−168.59 (11)
C9—C10—C11—C12	−2.0 (2)	C32—C31—P1—C1	−93.41 (15)
C9—C10—C11—S1	175.18 (12)	C36—C31—P1—C1	86.19 (12)
C8—C7—C12—O1	−177.71 (12)	C22—C21—P1—C31	−98.97 (13)
P2—C7—C12—O1	0.51 (17)	C26—C21—P1—C31	80.13 (12)
C8—C7—C12—C11	−0.8 (2)	C22—C21—P1—C1	3.88 (14)
P2—C7—C12—C11	177.42 (10)	C26—C21—P1—C1	−177.02 (12)
C10—C11—C12—C7	2.2 (2)	C6—C1—P1—C31	174.71 (11)
S1—C11—C12—C7	−174.93 (10)	C2—C1—P1—C31	−8.79 (13)
C10—C11—C12—O1	178.99 (13)	C6—C1—P1—C21	71.84 (12)
S1—C11—C12—O1	1.87 (18)	C2—C1—P1—C21	−111.66 (12)
C26—C21—C22—C23	0.0 (2)	C52—C51—P2—C41	71.69 (15)
P1—C21—C22—C23	179.12 (12)	C56—C51—P2—C41	−107.97 (14)
C21—C22—C23—C24	−0.4 (3)	C52—C51—P2—C7	−32.88 (15)
C22—C23—C24—C25	0.0 (3)	C56—C51—P2—C7	147.46 (13)
C23—C24—C25—C26	0.8 (2)	C46—C41—P2—C51	9.70 (14)
C24—C25—C26—C21	−1.2 (2)	C42—C41—P2—C51	−177.11 (12)
C22—C21—C26—C25	0.8 (2)	C46—C41—P2—C7	113.06 (13)
P1—C21—C26—C25	−178.36 (12)	C42—C41—P2—C7	−73.75 (12)
C36—C31—C32—C33	−0.3 (3)	C12—C7—P2—C51	−88.24 (12)
P1—C31—C32—C33	179.32 (15)	C8—C7—P2—C51	89.85 (13)
C31—C32—C33—C34	−0.2 (3)	C12—C7—P2—C41	167.38 (11)
C32—C33—C34—C35	0.1 (3)	C8—C7—P2—C41	−14.54 (13)
C33—C34—C35—C36	0.5 (3)	C4—C5—S1—C11	−150.31 (12)
C34—C35—C36—C31	−1.0 (2)	C6—C5—S1—C11	32.39 (12)
C32—C31—C36—C35	0.9 (2)	C10—C11—S1—C5	150.43 (12)
P1—C31—C36—C35	−178.76 (12)	C12—C11—S1—C5	−32.45 (13)