(−)-Menthyl (S_P,R_S)-(2-p-tolyl­sulfinyl­ethyl)phenyl­phosphinate

The title compound, C₂₅H₃₅O₃PS, is a chiral phosphinate containing five stereogenic centers, one at the P atom, one at the S atom and three in the (−)-menthyl group. The crystal packing reveals that mol­ecules are linked into chains along the a axis by inter­molecular C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.032
• wR factor = 0.082
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level A
SYMM004_ALERT_1_A  _symmetry_equiv_pos_as_xyz loop is missing.
            The symmetry equivalent positions in xyz.
            The following tests will not be performed.
            CELLZ_01,CHEMW_03,REFLT_03,SYMMG_01,SYMMG_02
PLAT124_ALERT_1_A Uninterpretable or Absent _symmetry_equiv_pos_as_xyz .    ?
PLAT728_ALERT_1_A D-H..A  Calc      104.00, Rep      139.00 Dev...      35.00 Deg.
              C2   -H2A  -O3      1.555   1.555   1.655

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         39 Perc.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S      -   O1      ..       5.51 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S      -   C11     ..       5.93 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    P      -   O3      ..       6.09 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C27
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.10

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: P.W. Osinski prepared the crystallization and composed the comment. J. Saadi carried out the synthesis of the title compound. L. Ricken carried out all analytical data. M. Sch\"urmann measured the diffraction data and H. Preut did the final refinements, composed the manuscript and is contact author. M. Pietrusiewicz developed these phosphorous chemistry and the starting materials. P. Eilbracht is the head of the catalysis group and together with Mr. Pietrusiewicz coordinates the cooperation.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995), PLATON (Spek, 2003).

(-)-Menthyl (S_P,R_S)-(2-p-tolylsulfinylethyl)phenylphosphinate

Crystal data

C25H35O3PS	F(000) = 960
Mr = 446.56	Dx = 1.167 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10129 reflections
a = 5.6199 (11) Å	θ = 3.0–29.0°
b = 16.824 (3) Å	µ = 0.21 mm^−1
c = 26.870 (5) Å	T = 291 K
V = 2540.6 (9) Å^3	Block, colourless
Z = 4	0.15 × 0.09 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1555 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Graphite monochromator	θmax = 25.0°, θmin = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −6→6
ω scans	k = −19→20
10129 measured reflections	l = −31→31
4029 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.032	w = [exp{5.20(sinθ/λ)^2}]/[σ^2(Fo^2)]
wR(F^2) = 0.082	(Δ/σ)max = 0.001
S = 0.89	Δρmax = 0.10 e Å^−3
4029 reflections	Δρmin = −0.09 e Å^−3
276 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0020 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 1472 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (10)

Special details

Experimental. For diastereomeric mixture: ¹H NMR (500 MHz, C₆D₆): δ 0.45 (d, 3H, J = 6.9 Hz), 0.7–1.05 (m, 9H), 1.25–1.5 (m, 5H), 1.98 (s, 3H), 2.02–2.2 (m, 2H), 2.6–2.85 (m, 2H), 3.3–3.45 (m, 1H), 4.15–4.3 (m, 1H), 6.82 (d, 2H, J 7.9), 7.02–7.12 (m, 3H), 7.30 (d, 2H, J 7.9), 7.75–7.85 (m, 2H); ³¹P NMR (81 MHz, C₆D₆): δ 40.3; ¹³C NMR (100 MHz, CDCl₃): δ 14.9 (CH₃), 20.9 (CH₃), 21.3 (CH₃), 21.9 (CH₃), d 20.8 and 21.7 (CH₂), 22.5 (CH₂), 25.2 (CH), 31.4 (CH), 33.9 (CH₂), 43.7 (CH₂), 48.2 (CH₂), 48.5 (CH), 77.2 (CH), 123.9 (CH), 128.5 (CH), 130.0 (CH), d 129.6 and 130.9 (Cq), 131.4 (CH), 132.4 (CH), 138.8 (Cq), 141.5 (Cq); IR (KBr plate): ν (cm^-1) 509 (s), 540 (s), 692 (m), 741 (m), 812 (s), 980 (vs), 1049 (vs), 1122 (m), 1221 (vs), 1417 (m), 2864 (m), 2945 (s), 2966 (m).

For (I): ¹H NMR (500 MHz, C₆D₆): δ 0.45 (d, 3H,J = 6.9 Hz), 0.6–1.1 (m, 9H), 1.25–1.5 (m, 5H), 2.03 (s, 3H), 2.05–2.2 (m, 2H), 2.6–2.9 (m, 3H). 3.3–3.45 (m, 1H), 4.35–4.5 (m, 1H), 6.90 (d, 2H, J = 7.9 Hz), 7.12–7.20 (m, 3H), 7.37 (d, 2H, J 7.9), 7.85–7.95 (m, 2H); ³¹P NMR (81 MHz, C₆D₆): δ 39.6; ¹³C NMR (100 MHz, CDCl₃): δ 15.5 (CH₃), 21.0 (CH₃), 21.4 (CH₃), 21.8 (CH₃), d 21.4 and 22.4 (CH₂), 22.7 (CH₂), 25.6 (CH), 31.4 (CH), 33.9 (CH₂), 43.1 (CH₂), 48.5 (CH₂), 48.6 (CH), 77.1 (CH), 124.1 (CH), 128.5 (CH), 130.0 (CH), 131.1 (Cq), 131.3 (CH), 132.4 (CH), 139.1 (Cq), 141.7 (Cq); IR (KBr plate): ν (cm^-1) 507 (m), 530 (m), 694 (m), 730 (m), 817 (m), 980 (s), 1049 (s), 1215 (vs), 1439 (m), 2858 (m), 2928 (s), 2951 (m)

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
S	0.4504 (2)	0.26812 (7)	0.36180 (4)	0.0856 (4)
P	−0.00906 (18)	0.20998 (6)	0.23586 (4)	0.0619 (3)
O1	0.3113 (6)	0.34075 (17)	0.37320 (12)	0.1239 (12)
O2	0.0071 (4)	0.26238 (12)	0.18666 (9)	0.0661 (7)
O3	−0.2430 (4)	0.21147 (15)	0.26060 (10)	0.0775 (8)
C1	0.2665 (6)	0.2099 (2)	0.32076 (14)	0.0711 (11)
H1A	0.3429	0.1592	0.3144	0.085*
H1B	0.1147	0.1996	0.3367	0.085*
C2	0.2247 (6)	0.2528 (2)	0.27139 (15)	0.0627 (11)
H2A	0.3702	0.2515	0.2520	0.075*
H2B	0.1869	0.3080	0.2781	0.075*
C11	0.4260 (8)	0.2040 (3)	0.41433 (15)	0.0680 (11)
C12	0.2447 (8)	0.2112 (3)	0.4479 (2)	0.0905 (14)
H12	0.1267	0.2492	0.4431	0.109*
C13	0.2372 (10)	0.1620 (4)	0.4889 (2)	0.1037 (17)
H13	0.1120	0.1672	0.5113	0.124*
C14	0.4078 (13)	0.1058 (3)	0.4977 (2)	0.0966 (16)
C15	0.5874 (10)	0.0991 (3)	0.4630 (3)	0.1007 (17)
H15	0.7042	0.0605	0.4673	0.121*
C16	0.5973 (8)	0.1479 (3)	0.42242 (19)	0.0894 (15)
H16	0.7225	0.1429	0.4000	0.107*
C17	0.3973 (11)	0.0532 (3)	0.54397 (19)	0.152 (3)
H17A	0.4156	−0.0014	0.5345	0.228*
H17B	0.2466	0.0602	0.5602	0.228*
H17C	0.5230	0.0679	0.5663	0.228*
C21	−0.1976 (7)	0.2693 (2)	0.15310 (15)	0.0677 (12)
H21	−0.3429	0.2708	0.1733	0.081*
C22	−0.1761 (6)	0.3469 (2)	0.12553 (15)	0.0632 (11)
H22	−0.0309	0.3436	0.1055	0.076*
C23	−0.3852 (8)	0.3527 (3)	0.08890 (16)	0.0895 (14)
H23A	−0.5323	0.3575	0.1075	0.107*
H23B	−0.3670	0.4003	0.0689	0.107*
C24	−0.4024 (8)	0.2811 (3)	0.05463 (17)	0.1050 (16)
H24A	−0.5413	0.2868	0.0335	0.126*
H24B	−0.2632	0.2796	0.0333	0.126*
C25	−0.4199 (8)	0.2033 (3)	0.08300 (17)	0.0917 (14)
H25	−0.5665	0.2047	0.1027	0.110*
C26	−0.2113 (7)	0.1987 (2)	0.11896 (16)	0.0803 (13)
H26A	−0.2258	0.1508	0.1388	0.096*
H26B	−0.0646	0.1951	0.1001	0.096*
C27	−0.1509 (8)	0.4199 (2)	0.15839 (17)	0.0774 (13)
H27	−0.0263	0.4076	0.1827	0.093*
C28	−0.0638 (9)	0.4924 (2)	0.12899 (17)	0.1159 (17)
H28A	0.0764	0.4785	0.1105	0.174*
H28B	−0.0273	0.5348	0.1516	0.174*
H28C	−0.1861	0.5093	0.1064	0.174*
C29	−0.3732 (8)	0.4405 (3)	0.18809 (18)	0.1134 (18)
H29A	−0.3393	0.4841	0.2100	0.170*
H29B	−0.4217	0.3952	0.2073	0.170*
H29C	−0.4987	0.4553	0.1657	0.170*
C30	−0.4319 (10)	0.1313 (3)	0.04916 (18)	0.139 (2)
H30A	−0.2928	0.1297	0.0285	0.208*
H30B	−0.5713	0.1347	0.0286	0.208*
H30C	−0.4393	0.0839	0.0690	0.208*
C31	0.0663 (7)	0.1117 (2)	0.21851 (14)	0.0579 (11)
C32	−0.0954 (7)	0.0517 (3)	0.22548 (17)	0.0825 (14)
H32	−0.2357	0.0625	0.2425	0.099*
C33	−0.0566 (10)	−0.0241 (3)	0.2080 (2)	0.1101 (19)
H33	−0.1698	−0.0636	0.2134	0.132*
C34	0.1470 (12)	−0.0413 (3)	0.1831 (2)	0.1030 (17)
H34	0.1728	−0.0925	0.1711	0.124*
C35	0.3143 (9)	0.0166 (4)	0.17553 (16)	0.0909 (15)
H35	0.4542	0.0048	0.1585	0.109*
C36	0.2743 (8)	0.0930 (3)	0.19339 (16)	0.0737 (12)
H36	0.3887	0.1321	0.1884	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0972 (9)	0.0820 (9)	0.0776 (8)	−0.0179 (7)	−0.0114 (7)	−0.0060 (7)
P	0.0528 (6)	0.0625 (7)	0.0702 (7)	0.0019 (6)	−0.0026 (7)	0.0059 (6)
O1	0.193 (3)	0.067 (2)	0.112 (3)	0.020 (2)	−0.026 (2)	−0.0165 (19)
O2	0.0555 (15)	0.0646 (16)	0.0782 (17)	−0.0015 (15)	−0.0069 (18)	0.0164 (13)
O3	0.0492 (13)	0.096 (2)	0.087 (2)	0.0058 (15)	0.0123 (15)	0.0046 (18)
C1	0.062 (2)	0.070 (3)	0.082 (3)	−0.006 (2)	−0.012 (2)	−0.005 (3)
C2	0.056 (2)	0.059 (3)	0.073 (3)	0.0012 (19)	−0.010 (2)	0.001 (2)
C11	0.074 (3)	0.070 (3)	0.060 (3)	−0.001 (3)	−0.007 (3)	−0.002 (3)
C12	0.078 (3)	0.104 (4)	0.089 (4)	0.006 (3)	0.010 (3)	−0.010 (4)
C13	0.097 (4)	0.134 (5)	0.081 (5)	−0.014 (4)	0.021 (4)	−0.019 (4)
C14	0.113 (5)	0.102 (5)	0.075 (4)	−0.019 (4)	−0.013 (4)	−0.007 (3)
C15	0.091 (4)	0.101 (4)	0.111 (5)	0.010 (3)	−0.008 (4)	0.007 (4)
C16	0.081 (4)	0.101 (4)	0.086 (4)	−0.002 (3)	0.010 (3)	0.006 (3)
C17	0.199 (7)	0.155 (5)	0.102 (5)	−0.049 (4)	−0.012 (4)	0.048 (4)
C21	0.055 (3)	0.069 (3)	0.079 (3)	0.005 (2)	−0.001 (2)	0.010 (3)
C22	0.055 (3)	0.064 (3)	0.070 (3)	0.005 (2)	−0.001 (2)	0.008 (3)
C23	0.104 (4)	0.088 (4)	0.076 (3)	0.009 (3)	−0.023 (3)	0.015 (3)
C24	0.142 (4)	0.089 (4)	0.084 (4)	−0.003 (4)	−0.034 (3)	0.003 (4)
C25	0.105 (4)	0.083 (4)	0.087 (4)	−0.018 (3)	−0.025 (3)	−0.001 (3)
C26	0.086 (3)	0.068 (3)	0.087 (3)	−0.003 (2)	−0.003 (3)	0.005 (3)
C27	0.082 (3)	0.063 (3)	0.088 (4)	0.004 (2)	−0.013 (3)	0.004 (3)
C28	0.141 (5)	0.069 (3)	0.137 (4)	0.003 (3)	−0.010 (4)	0.015 (3)
C29	0.105 (4)	0.122 (4)	0.113 (4)	0.025 (3)	0.001 (4)	−0.025 (3)
C30	0.200 (6)	0.096 (4)	0.120 (5)	−0.034 (4)	−0.045 (4)	0.000 (4)
C31	0.054 (3)	0.055 (3)	0.064 (3)	−0.007 (2)	−0.008 (2)	0.011 (2)
C32	0.071 (3)	0.062 (3)	0.115 (4)	−0.005 (3)	−0.009 (3)	0.018 (3)
C33	0.107 (5)	0.052 (4)	0.172 (6)	−0.011 (3)	−0.024 (4)	0.005 (3)
C34	0.130 (5)	0.063 (4)	0.117 (5)	0.024 (4)	−0.035 (4)	−0.010 (3)
C35	0.096 (4)	0.094 (4)	0.083 (4)	0.015 (4)	−0.004 (3)	−0.009 (3)
C36	0.072 (3)	0.065 (4)	0.085 (3)	−0.003 (2)	0.003 (3)	0.001 (3)

Geometric parameters (Å, º)

S—O1	1.483 (3)	C23—H23A	0.97
S—C11	1.782 (4)	C23—H23B	0.97
S—C1	1.801 (3)	C24—C25	1.517 (5)
P—O3	1.473 (2)	C24—H24A	0.97
P—O2	1.592 (2)	C24—H24B	0.97
P—C31	1.770 (4)	C25—C30	1.516 (5)
P—C2	1.776 (3)	C25—C26	1.521 (5)
O2—C21	1.466 (4)	C25—H25	0.98
C1—C2	1.529 (5)	C26—H26A	0.97
C1—H1A	0.97	C26—H26B	0.97
C1—H1B	0.97	C27—C29	1.522 (5)
C2—H2A	0.97	C27—C28	1.533 (5)
C2—H2B	0.97	C27—H27	0.98
C11—C16	1.366 (5)	C28—H28A	0.96
C11—C12	1.366 (5)	C28—H28B	0.96
C12—C13	1.380 (6)	C28—H28C	0.96
C12—H12	0.93	C29—H29A	0.96
C13—C14	1.367 (6)	C29—H29B	0.96
C13—H13	0.93	C29—H29C	0.96
C14—C15	1.379 (6)	C30—H30A	0.96
C14—C17	1.528 (6)	C30—H30B	0.96
C15—C16	1.365 (6)	C30—H30C	0.96
C15—H15	0.93	C31—C32	1.371 (5)
C16—H16	0.93	C31—C36	1.386 (5)
C17—H17A	0.96	C32—C33	1.376 (5)
C17—H17B	0.96	C32—H32	0.93
C17—H17C	0.96	C33—C34	1.357 (7)
C21—C26	1.502 (5)	C33—H33	0.93
C21—C22	1.507 (4)	C34—C35	1.369 (6)
C21—H21	0.98	C34—H34	0.93
C22—C27	1.519 (5)	C35—C36	1.391 (5)
C22—C23	1.536 (5)	C35—H35	0.93
C22—H22	0.98	C36—H36	0.93
C23—C24	1.519 (5)
O1—S—C11	107.1 (2)	C22—C23—H23B	109.0
O1—S—C1	105.81 (18)	H23A—C23—H23B	107.8
C11—S—C1	96.39 (18)	C25—C24—C23	112.5 (4)
O3—P—O2	114.60 (14)	C25—C24—H24A	109.1
O3—P—C31	110.38 (18)	C23—C24—H24A	109.1
O2—P—C31	106.57 (16)	C25—C24—H24B	109.1
O3—P—C2	114.24 (17)	C23—C24—H24B	109.1
O2—P—C2	100.35 (16)	H24A—C24—H24B	107.8
C31—P—C2	110.08 (17)	C30—C25—C24	113.0 (4)
C21—O2—P	120.7 (2)	C30—C25—C26	112.0 (4)
C2—C1—S	111.3 (3)	C24—C25—C26	108.2 (3)
C2—C1—H1A	109.4	C30—C25—H25	107.8
S—C1—H1A	109.4	C24—C25—H25	107.8
C2—C1—H1B	109.4	C26—C25—H25	107.8
S—C1—H1B	109.4	C21—C26—C25	112.8 (4)
H1A—C1—H1B	108.0	C21—C26—H26A	109.0
C1—C2—P	112.9 (2)	C25—C26—H26A	109.0
C1—C2—H2A	109.0	C21—C26—H26B	109.0
P—C2—H2A	109.0	C25—C26—H26B	109.0
C1—C2—H2B	109.0	H26A—C26—H26B	107.8
P—C2—H2B	109.0	C22—C27—C29	114.3 (4)
H2A—C2—H2B	107.8	C22—C27—C28	111.9 (4)
C16—C11—C12	118.8 (4)	C29—C27—C28	110.5 (4)
C16—C11—S	119.4 (4)	C22—C27—H27	106.5
C12—C11—S	121.8 (5)	C29—C27—H27	106.5
C11—C12—C13	119.8 (5)	C28—C27—H27	106.5
C11—C12—H12	120.1	C27—C28—H28A	109.5
C13—C12—H12	120.1	C27—C28—H28B	109.5
C14—C13—C12	122.1 (5)	H28A—C28—H28B	109.5
C14—C13—H13	119.0	C27—C28—H28C	109.5
C12—C13—H13	119.0	H28A—C28—H28C	109.5
C13—C14—C15	117.0 (5)	H28B—C28—H28C	109.5
C13—C14—C17	120.9 (7)	C27—C29—H29A	109.5
C15—C14—C17	122.1 (7)	C27—C29—H29B	109.5
C16—C15—C14	121.3 (5)	H29A—C29—H29B	109.5
C16—C15—H15	119.3	C27—C29—H29C	109.5
C14—C15—H15	119.3	H29A—C29—H29C	109.5
C15—C16—C11	120.9 (5)	H29B—C29—H29C	109.5
C15—C16—H16	119.5	C25—C30—H30A	109.5
C11—C16—H16	119.5	C25—C30—H30B	109.5
C14—C17—H17A	109.5	H30A—C30—H30B	109.5
C14—C17—H17B	109.5	C25—C30—H30C	109.5
H17A—C17—H17B	109.5	H30A—C30—H30C	109.5
C14—C17—H17C	109.5	H30B—C30—H30C	109.5
H17A—C17—H17C	109.5	C32—C31—C36	117.3 (4)
H17B—C17—H17C	109.5	C32—C31—P	119.6 (3)
O2—C21—C26	110.7 (3)	C36—C31—P	122.8 (3)
O2—C21—C22	107.9 (3)	C31—C32—C33	122.1 (4)
C26—C21—C22	112.9 (3)	C31—C32—H32	119.0
O2—C21—H21	108.4	C33—C32—H32	119.0
C26—C21—H21	108.4	C34—C33—C32	119.9 (5)
C22—C21—H21	108.4	C34—C33—H33	120.0
C21—C22—C27	115.0 (3)	C32—C33—H33	120.0
C21—C22—C23	108.0 (3)	C33—C34—C35	120.0 (5)
C27—C22—C23	113.2 (3)	C33—C34—H34	120.0
C21—C22—H22	106.7	C35—C34—H34	120.0
C27—C22—H22	106.7	C34—C35—C36	119.7 (5)
C23—C22—H22	106.7	C34—C35—H35	120.1
C24—C23—C22	112.8 (4)	C36—C35—H35	120.1
C24—C23—H23A	109.0	C31—C36—C35	121.0 (4)
C22—C23—H23A	109.0	C31—C36—H36	119.5
C24—C23—H23B	109.0	C35—C36—H36	119.5
O3—P—O2—C21	−35.6 (3)	C26—C21—C22—C23	55.1 (4)
C31—P—O2—C21	86.8 (3)	C21—C22—C23—C24	−54.1 (5)
C2—P—O2—C21	−158.4 (3)	C27—C22—C23—C24	177.4 (4)
O1—S—C1—C2	64.2 (3)	C22—C23—C24—C25	56.1 (5)
C11—S—C1—C2	174.1 (3)	C23—C24—C25—C30	−178.8 (4)
S—C1—C2—P	−165.93 (17)	C23—C24—C25—C26	−54.2 (5)
O3—P—C2—C1	61.1 (3)	O2—C21—C26—C25	−179.5 (3)
O2—P—C2—C1	−175.8 (3)	C22—C21—C26—C25	−58.4 (5)
C31—P—C2—C1	−63.7 (3)	C30—C25—C26—C21	−179.5 (4)
O1—S—C11—C16	−156.5 (3)	C24—C25—C26—C21	55.3 (5)
C1—S—C11—C16	94.7 (3)	C21—C22—C27—C29	−68.7 (5)
O1—S—C11—C12	21.1 (4)	C23—C22—C27—C29	56.0 (5)
C1—S—C11—C12	−87.7 (4)	C21—C22—C27—C28	164.7 (3)
C16—C11—C12—C13	−0.3 (7)	C23—C22—C27—C28	−70.6 (5)
S—C11—C12—C13	−177.9 (4)	O3—P—C31—C32	4.9 (4)
C11—C12—C13—C14	0.6 (8)	O2—P—C31—C32	−120.1 (3)
C12—C13—C14—C15	−1.3 (8)	C2—P—C31—C32	131.9 (3)
C12—C13—C14—C17	178.8 (4)	O3—P—C31—C36	178.3 (3)
C13—C14—C15—C16	1.7 (7)	O2—P—C31—C36	53.3 (4)
C17—C14—C15—C16	−178.3 (5)	C2—P—C31—C36	−54.7 (4)
C14—C15—C16—C11	−1.5 (7)	C36—C31—C32—C33	−0.6 (6)
C12—C11—C16—C15	0.7 (7)	P—C31—C32—C33	173.1 (4)
S—C11—C16—C15	178.4 (4)	C31—C32—C33—C34	0.0 (7)
P—O2—C21—C26	−81.9 (3)	C32—C33—C34—C35	0.4 (8)
P—O2—C21—C22	154.1 (2)	C33—C34—C35—C36	−0.2 (8)
O2—C21—C22—C27	−54.8 (4)	C32—C31—C36—C35	0.8 (6)
C26—C21—C22—C27	−177.5 (3)	P—C31—C36—C35	−172.7 (3)
O2—C21—C22—C23	177.8 (3)	C34—C35—C36—C31	−0.4 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3^i	0.97	2.29	3.085 (4)	139
C29—H29A···Cg^ii	0.96	2.86	3.695 (6)	146

Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+1/2.