2-[1-(Benzyl­phenyl­phosphinothio­yl)-2-phenyl­ethyl]-2'-[(E)-2-chloro­vinyl]-1,1'-binaphth­yl

The title compound, C₄₃H₃₄ClPS, is an unexpected reaction product that formed in the benzyl­ation of a dinaphthophos­phepine sulfide after addition of dichloro­methane in the presence of a strong base. It contains the rare functional group 2-chloro­vinyl in an E configuration, with C-C bond lengths of 1.471 (2) and 1.321 (2) Å, and a C-Cl bond length of 1.725 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.121
• Data-to-parameter ratio = 24.4

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.56
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.30 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.23 Ratio

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2-[1-(Benzylphenylphosphinothioyl)-2-phenylethyl]-2'-[(E)-2-chlorovinyl]- 1,1'-binaphthyl

Crystal data

C43H34ClPS	F(000) = 1360
Mr = 649.18	Dx = 1.241 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9934 reflections
a = 10.6924 (4) Å	θ = 2.2–29.9°
b = 19.6175 (7) Å	µ = 0.25 mm^−1
c = 16.5993 (6) Å	T = 173 K
β = 93.773 (1)°	Oval, colorless
V = 3474.3 (2) Å^3	0.58 × 0.54 × 0.52 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	10126 independent reflections
Radiation source: normal-focus sealed tube	8519 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −15→15
Tmin = 0.80, Tmax = 0.88	k = −27→27
51340 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0712P)^2 + 0.7845P] where P = (Fo^2 + 2Fc^2)/3
10126 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.69 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

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.

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.

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

	x	y	z	Uiso*/Ueq
P	0.03083 (3)	0.145011 (15)	0.281061 (17)	0.02178 (7)
S	−0.06734 (3)	0.228547 (16)	0.28813 (2)	0.03101 (8)
Cl	0.59536 (4)	0.34642 (2)	0.18534 (3)	0.05285 (11)
C1	0.31416 (10)	0.13085 (6)	0.13347 (7)	0.0221 (2)
C2	0.21121 (10)	0.16186 (6)	0.16418 (6)	0.0216 (2)
C3	0.12493 (11)	0.19784 (6)	0.11132 (7)	0.0277 (2)
H3	0.0571	0.2215	0.1328	0.033*
C4	0.13774 (13)	0.19903 (7)	0.02994 (8)	0.0315 (3)
H4	0.0789	0.2235	−0.0043	0.038*
C5	0.23749 (12)	0.16431 (6)	−0.00379 (7)	0.0285 (2)
C6	0.24908 (16)	0.16213 (7)	−0.08844 (8)	0.0389 (3)
H6	0.1893	0.1852	−0.1235	0.047*
C7	0.34467 (18)	0.12749 (8)	−0.11997 (8)	0.0449 (4)
H7	0.3505	0.1258	−0.1768	0.054*
C8	0.43450 (16)	0.09433 (8)	−0.06889 (9)	0.0437 (4)
H8	0.5012	0.0705	−0.0915	0.052*
C9	0.42780 (13)	0.09567 (7)	0.01363 (8)	0.0350 (3)
H9	0.4903	0.0735	0.0475	0.042*
C10	0.32755 (11)	0.13014 (6)	0.04824 (7)	0.0259 (2)
C11	0.41843 (10)	0.10268 (6)	0.18818 (7)	0.0248 (2)
C12	0.51940 (11)	0.14439 (7)	0.21185 (7)	0.0282 (2)
C13	0.61929 (12)	0.11758 (8)	0.26344 (9)	0.0382 (3)
H13	0.6893	0.1457	0.2786	0.046*
C14	0.61610 (13)	0.05254 (9)	0.29123 (9)	0.0414 (3)
H14	0.6840	0.0358	0.3255	0.050*
C15	0.51340 (13)	0.00932 (7)	0.27004 (8)	0.0349 (3)
C16	0.50693 (16)	−0.05794 (8)	0.30028 (10)	0.0444 (3)
H16	0.5730	−0.0747	0.3360	0.053*
C17	0.40801 (18)	−0.09891 (8)	0.27913 (11)	0.0496 (4)
H17	0.4044	−0.1436	0.3009	0.060*
C18	0.31040 (17)	−0.07532 (8)	0.22475 (11)	0.0452 (3)
H18	0.2419	−0.1044	0.2095	0.054*
C19	0.31407 (13)	−0.01037 (7)	0.19376 (9)	0.0342 (3)
H19	0.2485	0.0048	0.1566	0.041*
C20	0.41454 (11)	0.03414 (6)	0.21661 (7)	0.0279 (2)
C21	0.19533 (10)	0.16081 (6)	0.25435 (6)	0.0213 (2)
H21	0.2471	0.1221	0.2772	0.026*
C22	0.24903 (11)	0.22677 (6)	0.29475 (7)	0.0267 (2)
H22A	0.3263	0.2396	0.2687	0.032*
H22B	0.1875	0.2640	0.2846	0.032*
C23	0.27919 (12)	0.22092 (7)	0.38457 (7)	0.0288 (2)
C24	0.21339 (14)	0.25906 (8)	0.43862 (9)	0.0379 (3)
H24	0.1503	0.2901	0.4191	0.045*
C25	0.24054 (17)	0.25144 (9)	0.52159 (9)	0.0489 (4)
H25	0.1953	0.2774	0.5582	0.059*
C26	0.33163 (17)	0.20701 (10)	0.55099 (9)	0.0488 (4)
H26	0.3488	0.2021	0.6076	0.059*
C27	0.39831 (15)	0.16945 (9)	0.49781 (9)	0.0432 (3)
H27	0.4618	0.1388	0.5178	0.052*
C28	0.37247 (12)	0.17654 (8)	0.41500 (8)	0.0345 (3)
H28	0.4190	0.1508	0.3788	0.041*
C29	−0.03610 (11)	0.08525 (6)	0.20703 (7)	0.0268 (2)
C30	−0.12210 (14)	0.10916 (8)	0.14692 (9)	0.0379 (3)
H30	−0.1509	0.1549	0.1485	0.046*
C31	−0.16586 (17)	0.06649 (9)	0.08476 (10)	0.0499 (4)
H31	−0.2244	0.0831	0.0438	0.060*
C32	−0.12443 (19)	−0.00020 (9)	0.08224 (10)	0.0541 (4)
H32	−0.1527	−0.0290	0.0388	0.065*
C33	−0.04215 (18)	−0.02495 (8)	0.14273 (11)	0.0504 (4)
H33	−0.0157	−0.0711	0.1415	0.060*
C34	0.00238 (14)	0.01738 (7)	0.20560 (9)	0.0361 (3)
H34	0.0587	0.0001	0.2473	0.043*
C35	0.05520 (11)	0.09905 (7)	0.37694 (7)	0.0275 (2)
H35A	0.1029	0.0570	0.3670	0.033*
H35B	0.1084	0.1277	0.4145	0.033*
C36	−0.06063 (12)	0.07930 (7)	0.41888 (7)	0.0312 (3)
C37	−0.12535 (17)	0.12700 (10)	0.46142 (10)	0.0506 (4)
H37	−0.1012	0.1736	0.4609	0.061*
C38	−0.2260 (2)	0.10655 (14)	0.50509 (13)	0.0703 (6)
H38	−0.2704	0.1394	0.5341	0.084*
C39	−0.26158 (18)	0.03919 (14)	0.50659 (12)	0.0688 (6)
H39	−0.3297	0.0256	0.5369	0.083*
C40	−0.19865 (15)	−0.00829 (11)	0.46429 (10)	0.0536 (5)
H40	−0.2234	−0.0548	0.4650	0.064*
C41	−0.09855 (14)	0.01157 (8)	0.42041 (9)	0.0384 (3)
H41	−0.0554	−0.0216	0.3911	0.046*
C42	0.52167 (12)	0.21598 (7)	0.18572 (8)	0.0308 (3)
H42	0.4607	0.2300	0.1449	0.037*
C43	0.60235 (14)	0.26213 (8)	0.21497 (9)	0.0381 (3)
H43	0.6667	0.2484	0.2538	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.01942 (13)	0.02314 (14)	0.02288 (14)	0.00055 (10)	0.00215 (10)	0.00049 (10)
S	0.02517 (15)	0.02865 (15)	0.03962 (17)	0.00602 (11)	0.00539 (12)	−0.00097 (12)
Cl	0.0558 (2)	0.03640 (19)	0.0668 (3)	−0.00795 (16)	0.0076 (2)	−0.00863 (17)
C1	0.0220 (5)	0.0234 (5)	0.0209 (5)	−0.0005 (4)	0.0018 (4)	−0.0004 (4)
C2	0.0214 (5)	0.0232 (5)	0.0202 (5)	−0.0013 (4)	0.0012 (4)	−0.0001 (4)
C3	0.0256 (5)	0.0302 (6)	0.0270 (5)	0.0046 (4)	0.0008 (4)	0.0032 (4)
C4	0.0341 (6)	0.0332 (6)	0.0266 (6)	0.0027 (5)	−0.0017 (5)	0.0065 (5)
C5	0.0366 (6)	0.0273 (5)	0.0218 (5)	−0.0052 (5)	0.0028 (4)	0.0023 (4)
C6	0.0567 (9)	0.0379 (7)	0.0224 (6)	−0.0065 (6)	0.0050 (6)	0.0058 (5)
C7	0.0704 (11)	0.0418 (8)	0.0244 (6)	−0.0086 (7)	0.0168 (6)	0.0006 (5)
C8	0.0556 (9)	0.0424 (8)	0.0358 (7)	−0.0012 (7)	0.0239 (7)	−0.0051 (6)
C9	0.0375 (7)	0.0373 (7)	0.0315 (6)	0.0020 (5)	0.0125 (5)	−0.0017 (5)
C10	0.0299 (6)	0.0257 (5)	0.0226 (5)	−0.0036 (4)	0.0057 (4)	−0.0016 (4)
C11	0.0202 (5)	0.0319 (6)	0.0228 (5)	0.0041 (4)	0.0035 (4)	−0.0001 (4)
C12	0.0202 (5)	0.0382 (6)	0.0265 (5)	0.0006 (4)	0.0033 (4)	0.0016 (5)
C13	0.0226 (6)	0.0530 (8)	0.0383 (7)	0.0011 (5)	−0.0029 (5)	0.0054 (6)
C14	0.0301 (6)	0.0548 (9)	0.0384 (7)	0.0105 (6)	−0.0049 (5)	0.0090 (6)
C15	0.0348 (7)	0.0388 (7)	0.0315 (6)	0.0120 (5)	0.0049 (5)	0.0047 (5)
C16	0.0521 (9)	0.0402 (8)	0.0410 (8)	0.0169 (7)	0.0029 (6)	0.0092 (6)
C17	0.0662 (11)	0.0311 (7)	0.0522 (9)	0.0116 (7)	0.0090 (8)	0.0078 (6)
C18	0.0514 (9)	0.0284 (7)	0.0560 (9)	0.0012 (6)	0.0064 (7)	−0.0001 (6)
C19	0.0354 (7)	0.0289 (6)	0.0386 (7)	0.0039 (5)	0.0043 (5)	−0.0011 (5)
C20	0.0273 (5)	0.0302 (6)	0.0268 (5)	0.0072 (4)	0.0062 (4)	0.0000 (4)
C21	0.0194 (5)	0.0241 (5)	0.0205 (5)	0.0007 (4)	0.0017 (4)	−0.0016 (4)
C22	0.0268 (5)	0.0284 (5)	0.0250 (5)	−0.0046 (4)	0.0031 (4)	−0.0038 (4)
C23	0.0277 (6)	0.0336 (6)	0.0253 (5)	−0.0111 (5)	0.0034 (4)	−0.0059 (4)
C24	0.0404 (7)	0.0408 (7)	0.0333 (7)	−0.0095 (6)	0.0087 (5)	−0.0118 (5)
C25	0.0576 (10)	0.0585 (10)	0.0324 (7)	−0.0209 (8)	0.0160 (7)	−0.0186 (7)
C26	0.0541 (9)	0.0670 (11)	0.0250 (6)	−0.0293 (8)	−0.0006 (6)	−0.0026 (6)
C27	0.0371 (7)	0.0574 (9)	0.0340 (7)	−0.0168 (7)	−0.0072 (6)	0.0048 (6)
C28	0.0285 (6)	0.0452 (7)	0.0298 (6)	−0.0087 (5)	0.0008 (5)	−0.0028 (5)
C29	0.0250 (5)	0.0284 (6)	0.0270 (5)	−0.0054 (4)	0.0012 (4)	−0.0005 (4)
C30	0.0382 (7)	0.0362 (7)	0.0378 (7)	−0.0046 (6)	−0.0089 (6)	0.0017 (5)
C31	0.0561 (10)	0.0507 (9)	0.0404 (8)	−0.0161 (8)	−0.0168 (7)	0.0015 (7)
C32	0.0703 (12)	0.0477 (9)	0.0432 (8)	−0.0248 (8)	−0.0058 (8)	−0.0102 (7)
C33	0.0627 (11)	0.0327 (7)	0.0551 (9)	−0.0087 (7)	−0.0016 (8)	−0.0106 (7)
C34	0.0383 (7)	0.0293 (6)	0.0404 (7)	−0.0038 (5)	−0.0004 (6)	−0.0023 (5)
C35	0.0240 (5)	0.0330 (6)	0.0254 (5)	−0.0021 (4)	0.0008 (4)	0.0047 (4)
C36	0.0268 (6)	0.0421 (7)	0.0246 (5)	−0.0031 (5)	0.0006 (4)	0.0072 (5)
C37	0.0522 (9)	0.0579 (10)	0.0437 (8)	0.0022 (8)	0.0194 (7)	0.0037 (7)
C38	0.0579 (11)	0.0987 (17)	0.0580 (11)	0.0127 (11)	0.0322 (10)	0.0114 (11)
C39	0.0387 (9)	0.1160 (19)	0.0529 (10)	−0.0084 (10)	0.0121 (8)	0.0373 (12)
C40	0.0377 (8)	0.0748 (12)	0.0461 (9)	−0.0235 (8)	−0.0124 (7)	0.0318 (8)
C41	0.0338 (7)	0.0465 (8)	0.0335 (6)	−0.0106 (6)	−0.0077 (5)	0.0138 (6)
C42	0.0235 (5)	0.0398 (7)	0.0292 (6)	−0.0023 (5)	0.0035 (4)	0.0016 (5)
C43	0.0369 (7)	0.0385 (7)	0.0385 (7)	0.0001 (6)	−0.0005 (6)	−0.0076 (6)

Geometric parameters (Å, º)

P—C29	1.8113 (12)	C22—H22A	0.9900
P—C35	1.8328 (12)	C22—H22B	0.9900
P—C21	1.8678 (11)	C23—C28	1.393 (2)
P—S	1.9538 (4)	C23—C24	1.3938 (18)
C1—C2	1.3840 (15)	C24—C25	1.397 (2)
C1—C10	1.4314 (15)	C24—H24	0.9500
C1—C11	1.4966 (15)	C25—C26	1.373 (3)
C2—C3	1.4187 (16)	C25—H25	0.9500
C21—C2	1.5175 (15)	C26—C27	1.383 (3)
C3—C4	1.3669 (17)	C26—H26	0.9500
C3—H3	0.9500	C27—C28	1.3912 (19)
C4—C5	1.4119 (19)	C27—H27	0.9500
C4—H4	0.9500	C28—H28	0.9500
C5—C10	1.4190 (18)	C29—C30	1.3929 (18)
C5—C6	1.4194 (17)	C29—C34	1.3944 (19)
C6—C7	1.360 (2)	C30—C31	1.386 (2)
C6—H6	0.9500	C30—H30	0.9500
C7—C8	1.399 (3)	C31—C32	1.383 (3)
C7—H7	0.9500	C31—H31	0.9500
C8—C9	1.3766 (19)	C32—C33	1.379 (3)
C8—H8	0.9500	C32—H32	0.9500
C9—C10	1.4203 (17)	C33—C34	1.393 (2)
C9—H9	0.9500	C33—H33	0.9500
C11—C12	1.3906 (17)	C34—H34	0.9500
C11—C20	1.4265 (17)	C35—C36	1.5107 (17)
C12—C13	1.4249 (18)	C35—H35A	0.9900
C13—C14	1.358 (2)	C35—H35B	0.9900
C13—H13	0.9500	C36—C37	1.385 (2)
C14—C15	1.413 (2)	C36—C41	1.390 (2)
C14—H14	0.9500	C37—C38	1.395 (2)
C15—C16	1.415 (2)	C37—H37	0.9500
C15—C20	1.4203 (18)	C38—C39	1.376 (4)
C16—C17	1.356 (3)	C38—H38	0.9500
C16—H16	0.9500	C39—C40	1.369 (3)
C17—C18	1.412 (3)	C39—H39	0.9500
C17—H17	0.9500	C40—C41	1.389 (2)
C18—C19	1.376 (2)	C40—H40	0.9500
C18—H18	0.9500	C41—H41	0.9500
C19—C20	1.4165 (19)	C12—C42	1.4705 (19)
C19—H19	0.9500	C42—C43	1.3208 (19)
C21—C22	1.5503 (16)	C42—H42	0.9500
C21—H21	1.0000	C43—H43	0.9500
C22—C23	1.5090 (17)	C43—Cl	1.7253 (16)
C29—P—C35	107.34 (6)	C23—C22—C21	114.39 (10)
C29—P—C21	106.41 (5)	C23—C22—H22A	108.7
C35—P—C21	101.85 (5)	C21—C22—H22A	108.7
C29—P—S	113.19 (4)	C23—C22—H22B	108.7
C35—P—S	114.00 (4)	C21—C22—H22B	108.7
C21—P—S	113.15 (4)	H22A—C22—H22B	107.6
C2—C1—C10	120.14 (10)	C28—C23—C24	118.79 (13)
C2—C1—C11	121.18 (10)	C28—C23—C22	120.47 (11)
C10—C1—C11	118.49 (10)	C24—C23—C22	120.74 (13)
C1—C2—C3	119.44 (10)	C23—C24—C25	119.76 (16)
C1—C2—C21	120.04 (10)	C23—C24—H24	120.1
C3—C2—C21	120.42 (10)	C25—C24—H24	120.1
C4—C3—C2	121.09 (11)	C26—C25—C24	121.00 (15)
C4—C3—H3	119.5	C26—C25—H25	119.5
C2—C3—H3	119.5	C24—C25—H25	119.5
C3—C4—C5	120.74 (11)	C25—C26—C27	119.67 (14)
C3—C4—H4	119.6	C25—C26—H26	120.2
C5—C4—H4	119.6	C27—C26—H26	120.2
C4—C5—C10	119.12 (11)	C26—C27—C28	120.00 (16)
C4—C5—C6	121.64 (12)	C26—C27—H27	120.0
C10—C5—C6	119.23 (12)	C28—C27—H27	120.0
C7—C6—C5	120.84 (14)	C27—C28—C23	120.77 (14)
C7—C6—H6	119.6	C27—C28—H28	119.6
C5—C6—H6	119.6	C23—C28—H28	119.6
C6—C7—C8	120.16 (13)	C30—C29—C34	119.41 (12)
C6—C7—H7	119.9	C30—C29—P	118.74 (10)
C8—C7—H7	119.9	C34—C29—P	121.72 (10)
C9—C8—C7	121.04 (14)	C31—C30—C29	120.30 (14)
C9—C8—H8	119.5	C31—C30—H30	119.8
C7—C8—H8	119.5	C29—C30—H30	119.8
C8—C9—C10	120.11 (14)	C32—C31—C30	120.06 (15)
C8—C9—H9	119.9	C32—C31—H31	120.0
C10—C9—H9	119.9	C30—C31—H31	120.0
C5—C10—C9	118.60 (11)	C33—C32—C31	120.09 (15)
C5—C10—C1	119.27 (11)	C33—C32—H32	120.0
C9—C10—C1	122.12 (11)	C31—C32—H32	120.0
C12—C11—C20	120.01 (11)	C32—C33—C34	120.39 (16)
C12—C11—C1	119.18 (11)	C32—C33—H33	119.8
C20—C11—C1	120.80 (10)	C34—C33—H33	119.8
C11—C12—C13	119.33 (12)	C33—C34—C29	119.69 (14)
C11—C12—C42	120.41 (11)	C33—C34—H34	120.2
C13—C12—C42	120.23 (12)	C29—C34—H34	120.2
C14—C13—C12	121.09 (13)	C36—C35—P	116.89 (8)
C14—C13—H13	119.5	C36—C35—H35A	108.1
C12—C13—H13	119.5	P—C35—H35A	108.1
C13—C14—C15	121.03 (13)	C36—C35—H35B	108.1
C13—C14—H14	119.5	P—C35—H35B	108.1
C15—C14—H14	119.5	H35A—C35—H35B	107.3
C14—C15—C16	121.75 (13)	C37—C36—C41	118.72 (14)
C14—C15—C20	118.94 (13)	C37—C36—C35	120.93 (13)
C16—C15—C20	119.30 (14)	C41—C36—C35	120.17 (13)
C17—C16—C15	121.08 (14)	C36—C37—C38	119.94 (19)
C17—C16—H16	119.5	C36—C37—H37	120.0
C15—C16—H16	119.5	C38—C37—H37	120.0
C16—C17—C18	120.15 (15)	C39—C38—C37	120.6 (2)
C16—C17—H17	119.9	C39—C38—H38	119.7
C18—C17—H17	119.9	C37—C38—H38	119.7
C19—C18—C17	120.30 (16)	C40—C39—C38	119.89 (16)
C19—C18—H18	119.9	C40—C39—H39	120.1
C17—C18—H18	119.9	C38—C39—H39	120.1
C18—C19—C20	120.70 (14)	C39—C40—C41	119.97 (18)
C18—C19—H19	119.6	C39—C40—H40	120.0
C20—C19—H19	119.6	C41—C40—H40	120.0
C19—C20—C15	118.43 (12)	C40—C41—C36	120.88 (17)
C19—C20—C11	122.04 (11)	C40—C41—H41	119.6
C15—C20—C11	119.53 (12)	C36—C41—H41	119.6
C2—C21—C22	110.66 (9)	C12—C42—C43	124.70 (13)
C2—C21—P	113.87 (7)	C43—C42—H42	117.6
C22—C21—P	111.32 (8)	C12—C42—H42	117.6
C2—C21—H21	106.9	C42—C43—Cl	122.49 (12)
C22—C21—H21	106.9	C42—C43—H43	118.8
P—C21—H21	106.9	Cl—C43—H43	118.8
C10—C1—C2—C3	−5.34 (17)	C1—C2—C21—C22	94.86 (12)
C11—C1—C2—C3	169.54 (11)	C3—C2—C21—C22	−81.50 (13)
C10—C1—C2—C21	178.26 (10)	C1—C2—C21—P	−138.86 (9)
C11—C1—C2—C21	−6.86 (16)	C3—C2—C21—P	44.78 (13)
C1—C2—C3—C4	3.88 (18)	C29—P—C21—C2	35.99 (9)
C21—C2—C3—C4	−179.74 (11)	C35—P—C21—C2	148.28 (8)
C2—C3—C4—C5	0.0 (2)	S—P—C21—C2	−88.92 (8)
C3—C4—C5—C10	−2.39 (19)	C29—P—C21—C22	161.93 (8)
C3—C4—C5—C6	176.90 (13)	C35—P—C21—C22	−85.78 (9)
C4—C5—C6—C7	−178.91 (14)	S—P—C21—C22	37.02 (9)
C10—C5—C6—C7	0.4 (2)	C2—C21—C22—C23	−159.72 (10)
C5—C6—C7—C8	−1.1 (2)	P—C21—C22—C23	72.59 (12)
C6—C7—C8—C9	0.4 (2)	C21—C22—C23—C28	64.48 (15)
C7—C8—C9—C10	1.0 (2)	C21—C22—C23—C24	−114.70 (13)
C4—C5—C10—C9	−179.70 (12)	C28—C23—C24—C25	−0.9 (2)
C6—C5—C10—C9	0.99 (18)	C22—C23—C24—C25	178.24 (13)
C4—C5—C10—C1	0.88 (17)	C23—C24—C25—C26	0.2 (2)
C6—C5—C10—C1	−178.43 (11)	C24—C25—C26—C27	0.4 (2)
C8—C9—C10—C5	−1.7 (2)	C25—C26—C27—C28	−0.3 (2)
C8—C9—C10—C1	177.72 (13)	C26—C27—C28—C23	−0.4 (2)
C2—C1—C10—C5	3.01 (17)	C24—C23—C28—C27	1.05 (19)
C11—C1—C10—C5	−172.01 (11)	C22—C23—C28—C27	−178.14 (12)
C2—C1—C10—C9	−176.39 (12)	C35—P—C29—C30	145.98 (11)
C11—C1—C10—C9	8.59 (17)	C21—P—C29—C30	−105.58 (11)
C2—C1—C11—C12	−90.49 (14)	S—P—C29—C30	19.31 (12)
C10—C1—C11—C12	84.48 (14)	C35—P—C29—C34	−38.33 (12)
C2—C1—C11—C20	88.92 (14)	C21—P—C29—C34	70.11 (12)
C10—C1—C11—C20	−96.12 (13)	S—P—C29—C34	−165.00 (10)
C20—C11—C12—C13	1.07 (17)	C34—C29—C30—C31	−2.1 (2)
C1—C11—C12—C13	−179.52 (11)	P—C29—C30—C31	173.65 (13)
C20—C11—C12—C42	−177.34 (11)	C29—C30—C31—C32	0.1 (3)
C1—C11—C12—C42	2.07 (17)	C30—C31—C32—C33	1.8 (3)
C11—C12—C13—C14	−1.5 (2)	C31—C32—C33—C34	−1.7 (3)
C42—C12—C13—C14	176.92 (13)	C32—C33—C34—C29	−0.3 (3)
C12—C13—C14—C15	−0.1 (2)	C30—C29—C34—C33	2.2 (2)
C13—C14—C15—C16	−178.19 (14)	P—C29—C34—C33	−173.43 (12)
C13—C14—C15—C20	2.1 (2)	C29—P—C35—C36	−70.27 (11)
C14—C15—C16—C17	−179.72 (15)	C21—P—C35—C36	178.15 (10)
C20—C15—C16—C17	−0.1 (2)	S—P—C35—C36	55.93 (11)
C15—C16—C17—C18	1.4 (3)	P—C35—C36—C37	−77.21 (16)
C16—C17—C18—C19	−0.9 (3)	P—C35—C36—C41	107.65 (13)
C17—C18—C19—C20	−0.9 (2)	C41—C36—C37—C38	0.4 (3)
C18—C19—C20—C15	2.13 (19)	C35—C36—C37—C38	−174.82 (16)
C18—C19—C20—C11	−177.34 (13)	C36—C37—C38—C39	0.2 (3)
C14—C15—C20—C19	178.00 (12)	C37—C38—C39—C40	−0.6 (3)
C16—C15—C20—C19	−1.68 (19)	C38—C39—C40—C41	0.4 (3)
C14—C15—C20—C11	−2.51 (18)	C39—C40—C41—C36	0.2 (2)
C16—C15—C20—C11	177.81 (12)	C37—C36—C41—C40	−0.6 (2)
C12—C11—C20—C19	−179.61 (11)	C35—C36—C41—C40	174.65 (12)
C1—C11—C20—C19	0.99 (17)	C11—C12—C42—C43	168.68 (13)
C12—C11—C20—C15	0.92 (17)	C13—C12—C42—C43	−9.7 (2)
C1—C11—C20—C15	−178.47 (11)	C12—C42—C43—Cl	−176.72 (10)