Triethyl-ammonium O-3β-cholest-5-en-3-yl (4-meth-oxy-phen-yl)dithio-phospho-nate.

In the crystal structure of the title compound, C(6)H(16)N(+)·C(34)H(52)O(2)PS(2) (-) or [(CH(3)CH(2))(3)NH](+)·[C(34)H(52)O(2)PS(2)](-), the cation and anion are paired via weak, inter-molecular, bifurcated N-H⋯(S,S) hydrogen bonds. The cholesteryl units form an alternating (herringbone) motif as well as an infinitely stacked layered structure along the b axis. The P-S bond lengths [1.975 (2) and 1.981 (2) Å compared with ca 1.92 Å for a formal P=S double bond and with ca 2.01 Å for a P-S single bond] suggest delocalization of the negative charge between the P-S bonds. A distorted tetra-hedral geometry around the P atom is revealed by non-ideal O-P-C and S-P-S bond angles of 96.7 (2) and 115.52 (11)°, respectively.

Related literature

For applications of dithio­phospho­nate derivatives, see: Beaton et al. (1991 ▶); Patnaik (1992 ▶); Roy (1990 ▶); Bromberg et al. (1993 ▶); Klaman (1984 ▶). For information on dithio­phospho­nate compounds, see: van Zyl et al. (1998 ▶, 2000 ▶, 2002 ▶); van Zyl et al. (2010 ▶). For P/S activation of steroids, see: Kvasnica et al. (2008 ▶). For related structures, see: Malenkovskaya et al. (2003 ▶); Cea-Olivares et al. (1999 ▶); Blaszczyk et al. (1996 ▶).

Experimental

Crystal data

C6H16N+·C34H52O2PS2 −

M = 690.04

Monoclinic,

a = 7.6066 (15) Å

b = 8.2407 (16) Å

c = 33.083 (7) Å

β = 93.17 (3)°

V = 2070.6 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.46 × 0.08 × 0.08 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.914, T max = 0.984

14589 measured reflections

8425 independent reflections

2925 reflections with I > 2σ(I)

R int = 0.106

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.159

S = 0.93

8425 reflections

410 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 2970 Friedel pairs

Flack parameter: 0.02 (12)

Data collection: SMART-NT (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 1999 ▶); program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Brendt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029703/cv2748sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029703/cv2748Isup2.hkl

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

C6H16N+·C34H52O2PS2−	F(000) = 756
Mr = 690.04	Dx = 1.107 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 714 reflections
a = 7.6066 (15) Å	θ = 2.5–18°
b = 8.2407 (16) Å	µ = 0.20 mm−1
c = 33.083 (7) Å	T = 293 K
β = 93.17 (3)°	Needle, colourless
V = 2070.6 (7) Å3	0.46 × 0.08 × 0.08 mm
Z = 2

Bruker SMART 1K CCD diffractometer	8425 independent reflections
Radiation source: fine-focus sealed tube	2925 reflections with I > 2σ(I)
graphite	Rint = 0.106
ω scans	θmax = 28.3°, θmin = 0.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→9
Tmin = 0.914, Tmax = 0.984	k = −8→10
14589 measured reflections	l = −44→41

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.3561P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.066	(Δ/σ)max = 0.001
wR(F2) = 0.159	Δρmax = 0.29 e Å−3
S = 0.93	Δρmin = −0.28 e Å−3
8425 reflections	Absolute structure: Flack (1983), 2970 Friedel pairs
410 parameters	Flack parameter: 0.02 (12)
1 restraint

Experimental. The intensity data was collected on a Bruker SMART 1 K CCD diffractometer using an exposure time of 10 s/frame. A total of 1315 frames were collected with a frame width of 0.3° covering up to θ = 28.3° with 99.8% completeness accomplished.

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.

	x	y	z	Uiso*/Ueq
P	0.4405 (2)	0.9520 (2)	0.64139 (5)	0.0564 (5)
S1	0.6976 (2)	0.9298 (2)	0.63620 (6)	0.0765 (6)
S2	0.3618 (2)	1.1632 (2)	0.66205 (5)	0.0787 (6)
N	0.7566 (8)	0.3414 (8)	0.64246 (16)	0.0629 (16)
O1	0.3661 (5)	0.8058 (4)	0.66822 (10)	0.0582 (12)
O2	0.0389 (9)	0.7700 (7)	0.48803 (16)	0.117 (2)
C1	0.3206 (8)	0.8992 (7)	0.59454 (18)	0.0553 (17)
C2	0.4030 (9)	0.8534 (9)	0.5604 (2)	0.089 (3)
H2	0.5253	0.8519	0.5605	0.107*
C3	0.3002 (12)	0.8082 (11)	0.5251 (2)	0.108 (3)
H3	0.3555	0.7742	0.5021	0.13*
C4	0.1217 (11)	0.8144 (9)	0.5245 (2)	0.078 (2)
C5	0.0390 (9)	0.8652 (7)	0.5579 (2)	0.0653 (19)
H5	−0.0831	0.8733	0.5571	0.078*
C6	0.1382 (9)	0.9046 (7)	0.59280 (19)	0.0632 (18)
H6	0.081	0.9354	0.6157	0.076*
C7	−0.1478 (13)	0.7738 (12)	0.4851 (2)	0.130 (3)
H7A	−0.1928	0.6977	0.5039	0.195*
H7B	−0.1893	0.7453	0.4581	0.195*
H7C	−0.1878	0.881	0.4913	0.195*
C8	0.3646 (8)	0.8128 (7)	0.71259 (16)	0.0540 (16)
H8	0.4108	0.9181	0.722	0.065*
C9	0.1781 (8)	0.7960 (9)	0.72416 (17)	0.073 (2)
H9A	0.1281	0.6959	0.7132	0.087*
H9B	0.1082	0.8859	0.7132	0.087*
C10	0.1755 (8)	0.7948 (8)	0.77036 (17)	0.0672 (19)
H10A	0.0545	0.785	0.7778	0.081*
H10B	0.2202	0.8979	0.7806	0.081*
C11	0.2848 (7)	0.6567 (8)	0.79104 (15)	0.0478 (15)
C12	0.4698 (8)	0.6673 (7)	0.77557 (16)	0.0491 (15)
C13	0.4797 (7)	0.6801 (8)	0.73037 (16)	0.0618 (17)
H13A	0.6007	0.7006	0.724	0.074*
H13B	0.4442	0.5775	0.7181	0.074*
C14	0.2057 (9)	0.4918 (8)	0.78016 (18)	0.085 (2)
H14A	0.2334	0.4635	0.7531	0.127*
H14B	0.0802	0.4962	0.7818	0.127*
H14C	0.2537	0.4115	0.7987	0.127*
C15	0.2930 (6)	0.6876 (7)	0.83762 (16)	0.0490 (16)
H15	0.3168	0.8036	0.8415	0.059*
C16	0.4436 (7)	0.5964 (7)	0.86033 (15)	0.0474 (15)
H16	0.4254	0.4797	0.8562	0.057*
C17	0.6186 (6)	0.6417 (8)	0.84456 (16)	0.0597 (17)
H17A	0.6575	0.7433	0.8568	0.072*
H17B	0.7043	0.5591	0.8526	0.072*
C18	0.6129 (8)	0.6594 (8)	0.79945 (17)	0.0557 (16)
H18	0.7202	0.6653	0.7873	0.067*
C19	0.1159 (6)	0.6524 (8)	0.85715 (15)	0.0594 (16)
H19A	0.026	0.7225	0.8447	0.071*
H19B	0.0819	0.5412	0.8511	0.071*
C20	0.1201 (7)	0.6770 (8)	0.90307 (15)	0.0554 (16)
H20A	0.0083	0.643	0.913	0.067*
H20B	0.135	0.7915	0.9091	0.067*
C21	0.2691 (7)	0.5811 (7)	0.92521 (16)	0.0449 (15)
C22	0.4385 (6)	0.6324 (7)	0.90520 (14)	0.0423 (14)
H22	0.4434	0.7509	0.9075	0.051*
C23	0.2355 (8)	0.3976 (7)	0.92165 (15)	0.0570 (17)
H23A	0.2346	0.366	0.8937	0.085*
H23B	0.1239	0.3722	0.9323	0.085*
H23C	0.3271	0.3401	0.9368	0.085*
C24	0.3149 (6)	0.6274 (6)	0.96991 (15)	0.0433 (14)
H24	0.3076	0.7459	0.9716	0.052*
C25	0.5127 (7)	0.5825 (7)	0.97587 (16)	0.0527 (16)
H25A	0.5753	0.6655	0.9917	0.063*
H25B	0.5259	0.48	0.9901	0.063*
C26	0.5878 (7)	0.5689 (8)	0.93369 (17)	0.0583 (17)
H26A	0.6928	0.6348	0.932	0.07*
H26B	0.6161	0.4572	0.9274	0.07*
C27	0.2062 (7)	0.5588 (7)	1.00409 (16)	0.0478 (15)
H27	0.2239	0.4411	1.0047	0.057*
C28	0.0093 (8)	0.5893 (7)	0.99762 (17)	0.0617 (18)
H28A	−0.049	0.5552	1.0212	0.093*
H28B	−0.0359	0.5289	0.9745	0.093*
H28C	−0.0112	0.7029	0.9931	0.093*
C29	0.2764 (8)	0.6252 (8)	1.04439 (15)	0.0656 (19)
H29A	0.2584	0.7418	1.044	0.079*
H29B	0.4025	0.6069	1.0464	0.079*
C30	0.2014 (8)	0.5599 (7)	1.08297 (16)	0.0611 (18)
H30A	0.0777	0.5885	1.0832	0.073*
H30B	0.2099	0.4425	1.0831	0.073*
C31	0.2976 (11)	0.6267 (10)	1.12087 (19)	0.1104 (14)
H31A	0.4189	0.5903	1.1211	0.132*
H31B	0.2988	0.7441	1.1187	0.132*
C32	0.2273 (11)	0.5835 (10)	1.1606 (2)	0.1104 (14)
H32	0.2151	0.4651	1.1612	0.132*
C33	0.0500 (10)	0.6538 (10)	1.16635 (19)	0.1104 (14)
H33A	0.0569	0.7701	1.1655	0.166*
H33B	0.0104	0.6204	1.1921	0.166*
H33C	−0.0314	0.6163	1.1452	0.166*
C34	0.3558 (10)	0.6306 (10)	1.19511 (18)	0.1104 (14)
H34A	0.3734	0.7459	1.1949	0.166*
H34B	0.4662	0.5768	1.192	0.166*
H34C	0.3093	0.599	1.2203	0.166*
C35	0.9219 (8)	0.3208 (8)	0.62051 (19)	0.0705 (19)
H35A	0.8913	0.2858	0.593	0.085*
H35B	0.9926	0.236	0.6337	0.085*
C36	1.0308 (9)	0.4735 (10)	0.6191 (2)	0.115 (3)
H36A	0.9634	0.5571	0.6052	0.172*
H36B	1.1353	0.4522	0.605	0.172*
H36C	1.0631	0.5084	0.6462	0.172*
C37	0.7919 (10)	0.3745 (9)	0.6876 (2)	0.091 (2)
H37A	0.8507	0.4785	0.6907	0.109*
H37B	0.6799	0.3828	0.7001	0.109*
C38	0.9001 (11)	0.2499 (10)	0.7094 (2)	0.109 (3)
H38A	0.8464	0.1454	0.7053	0.164*
H38B	0.9083	0.2748	0.7378	0.164*
H38C	1.0159	0.2488	0.6992	0.164*
C39	0.6301 (10)	0.4630 (10)	0.6243 (2)	0.099 (2)
H39A	0.6847	0.5693	0.6252	0.119*
H39B	0.527	0.4674	0.6402	0.119*
C40	0.5737 (11)	0.4232 (12)	0.5813 (2)	0.130 (3)
H40A	0.6695	0.4434	0.5642	0.195*
H40B	0.475	0.4898	0.5727	0.195*
H40C	0.5406	0.3109	0.5794	0.195*
H1	0.705 (9)	0.235 (8)	0.6428 (19)	0.11 (3)*

	U11	U22	U33	U12	U13	U23
P	0.0556 (11)	0.0558 (12)	0.0586 (11)	−0.0041 (10)	0.0114 (9)	0.0045 (10)
S1	0.0517 (11)	0.0771 (14)	0.1017 (15)	−0.0014 (10)	0.0143 (10)	−0.0089 (11)
S2	0.0778 (13)	0.0637 (12)	0.0961 (14)	0.0056 (11)	0.0175 (11)	−0.0043 (11)
N	0.068 (4)	0.053 (4)	0.068 (4)	0.000 (4)	0.008 (3)	−0.003 (3)
O1	0.073 (3)	0.060 (3)	0.042 (3)	−0.016 (2)	0.007 (2)	0.007 (2)
O2	0.106 (5)	0.182 (6)	0.060 (4)	0.025 (4)	−0.010 (3)	−0.019 (3)
C1	0.053 (4)	0.063 (4)	0.050 (4)	0.002 (3)	0.006 (3)	0.017 (3)
C2	0.069 (5)	0.153 (8)	0.046 (5)	0.021 (5)	0.012 (4)	0.010 (4)
C3	0.098 (7)	0.177 (9)	0.051 (6)	0.027 (6)	0.016 (5)	−0.028 (5)
C4	0.070 (6)	0.107 (6)	0.058 (6)	0.012 (5)	−0.006 (5)	0.002 (4)
C5	0.065 (5)	0.078 (5)	0.054 (4)	0.009 (4)	0.007 (4)	0.003 (4)
C6	0.063 (5)	0.072 (5)	0.055 (5)	−0.007 (4)	0.006 (4)	−0.001 (4)
C7	0.120 (9)	0.177 (10)	0.087 (6)	−0.010 (7)	−0.037 (6)	−0.024 (6)
C8	0.058 (4)	0.064 (4)	0.041 (4)	0.001 (4)	0.009 (3)	−0.001 (3)
C9	0.056 (5)	0.111 (6)	0.052 (5)	0.012 (4)	0.008 (4)	0.013 (4)
C10	0.046 (4)	0.106 (6)	0.051 (4)	0.011 (4)	0.004 (3)	0.009 (4)
C11	0.044 (4)	0.066 (4)	0.034 (3)	−0.014 (4)	0.004 (3)	0.008 (3)
C12	0.044 (4)	0.060 (4)	0.044 (4)	0.005 (3)	0.007 (3)	0.002 (3)
C13	0.051 (4)	0.077 (5)	0.058 (4)	0.002 (4)	0.010 (3)	0.005 (4)
C14	0.094 (5)	0.105 (6)	0.055 (4)	−0.042 (5)	0.003 (4)	0.000 (4)
C15	0.027 (3)	0.067 (4)	0.053 (4)	0.001 (3)	0.005 (3)	0.006 (3)
C16	0.036 (4)	0.059 (4)	0.047 (4)	−0.001 (3)	−0.003 (3)	−0.001 (3)
C17	0.033 (4)	0.087 (5)	0.060 (4)	0.002 (4)	0.008 (3)	0.014 (4)
C18	0.040 (4)	0.072 (4)	0.056 (4)	0.004 (4)	0.009 (3)	0.006 (4)
C19	0.033 (4)	0.089 (5)	0.056 (4)	0.007 (4)	−0.003 (3)	0.010 (4)
C20	0.034 (4)	0.087 (5)	0.046 (4)	0.003 (4)	0.008 (3)	0.012 (4)
C21	0.039 (4)	0.051 (4)	0.045 (4)	0.001 (3)	−0.001 (3)	0.000 (3)
C22	0.032 (3)	0.053 (4)	0.041 (4)	0.000 (3)	−0.006 (3)	0.001 (3)
C23	0.068 (4)	0.059 (5)	0.044 (4)	−0.012 (3)	0.005 (3)	−0.003 (3)
C24	0.046 (4)	0.037 (4)	0.047 (4)	0.002 (3)	0.000 (3)	0.000 (3)
C25	0.043 (4)	0.064 (4)	0.049 (4)	−0.005 (3)	−0.009 (3)	0.000 (3)
C26	0.035 (4)	0.082 (4)	0.058 (4)	0.008 (3)	0.005 (3)	0.010 (3)
C27	0.048 (4)	0.044 (4)	0.051 (4)	−0.005 (3)	0.000 (3)	−0.001 (3)
C28	0.059 (5)	0.065 (5)	0.062 (4)	0.003 (3)	0.019 (3)	0.004 (3)
C29	0.079 (5)	0.074 (5)	0.044 (4)	−0.019 (4)	0.007 (3)	−0.003 (4)
C30	0.084 (5)	0.063 (4)	0.036 (4)	−0.006 (4)	0.006 (3)	0.000 (3)
C31	0.152 (4)	0.123 (4)	0.056 (2)	0.010 (3)	0.008 (3)	−0.006 (3)
C32	0.152 (4)	0.123 (4)	0.056 (2)	0.010 (3)	0.008 (3)	−0.006 (3)
C33	0.152 (4)	0.123 (4)	0.056 (2)	0.010 (3)	0.008 (3)	−0.006 (3)
C34	0.152 (4)	0.123 (4)	0.056 (2)	0.010 (3)	0.008 (3)	−0.006 (3)
C35	0.068 (5)	0.073 (5)	0.071 (5)	0.002 (4)	0.010 (4)	−0.005 (4)
C36	0.091 (6)	0.086 (6)	0.171 (8)	−0.005 (5)	0.044 (5)	0.026 (6)
C37	0.103 (6)	0.091 (6)	0.079 (6)	−0.020 (5)	0.016 (5)	−0.034 (4)
C38	0.111 (7)	0.132 (8)	0.084 (6)	−0.014 (6)	−0.008 (5)	0.007 (5)
C39	0.088 (6)	0.074 (5)	0.135 (7)	0.007 (5)	0.004 (5)	0.017 (6)
C40	0.116 (7)	0.167 (9)	0.105 (7)	0.010 (7)	−0.011 (6)	0.054 (7)

P—O1	1.617 (4)	C21—C23	1.537 (7)
P—C1	1.807 (6)	C21—C22	1.540 (7)
P—S2	1.975 (2)	C21—C24	1.548 (7)
P—S1	1.981 (2)	C22—C26	1.528 (7)
N—C39	1.493 (8)	C22—H22	0.98
N—C35	1.496 (7)	C23—H23A	0.96
N—C37	1.526 (8)	C23—H23B	0.96
N—H1	0.96 (7)	C23—H23C	0.96
O1—C8	1.470 (6)	C24—C27	1.545 (7)
O2—C4	1.379 (8)	C24—C25	1.551 (7)
O2—C7	1.419 (9)	C24—H24	0.98
C1—C2	1.374 (8)	C25—C26	1.541 (7)
C1—C6	1.387 (7)	C25—H25A	0.97
C2—C3	1.421 (9)	C25—H25B	0.97
C2—H2	0.93	C26—H26A	0.97
C3—C4	1.357 (9)	C26—H26B	0.97
C3—H3	0.93	C27—C29	1.511 (7)
C4—C5	1.367 (8)	C27—C28	1.522 (7)
C5—C6	1.383 (8)	C27—H27	0.98
C5—H5	0.93	C28—H28A	0.96
C6—H6	0.93	C28—H28B	0.96
C7—H7A	0.96	C28—H28C	0.96
C7—H7B	0.96	C29—C30	1.525 (7)
C7—H7C	0.96	C29—H29A	0.97
C8—C9	1.496 (7)	C29—H29B	0.97
C8—C13	1.501 (7)	C30—C31	1.520 (8)
C8—H8	0.98	C30—H30A	0.97
C9—C10	1.530 (7)	C30—H30B	0.97
C9—H9A	0.97	C31—C32	1.488 (9)
C9—H9B	0.97	C31—H31A	0.97
C10—C11	1.546 (8)	C31—H31B	0.97
C10—H10A	0.97	C32—C33	1.490 (9)
C10—H10B	0.97	C32—C34	1.512 (9)
C11—C14	1.521 (8)	C32—H32	0.98
C11—C12	1.527 (7)	C33—H33A	0.96
C11—C15	1.559 (7)	C33—H33B	0.96
C12—C18	1.311 (7)	C33—H33C	0.96
C12—C13	1.505 (7)	C34—H34A	0.96
C13—H13A	0.97	C34—H34B	0.96
C13—H13B	0.97	C34—H34C	0.96
C14—H14A	0.96	C35—C36	1.508 (9)
C14—H14B	0.96	C35—H35A	0.97
C14—H14C	0.96	C35—H35B	0.97
C15—C16	1.532 (7)	C36—H36A	0.96
C15—C19	1.553 (6)	C36—H36B	0.96
C15—H15	0.98	C36—H36C	0.96
C16—C17	1.503 (6)	C37—C38	1.479 (9)
C16—C22	1.516 (6)	C37—H37A	0.97
C16—H16	0.98	C37—H37B	0.97
C17—C18	1.498 (7)	C38—H38A	0.96
C17—H17A	0.97	C38—H38B	0.96
C17—H17B	0.97	C38—H38C	0.96
C18—H18	0.93	C39—C40	1.498 (9)
C19—C20	1.531 (6)	C39—H39A	0.97
C19—H19A	0.97	C39—H39B	0.97
C19—H19B	0.97	C40—H40A	0.96
C20—C21	1.534 (7)	C40—H40B	0.96
C20—H20A	0.97	C40—H40C	0.96
C20—H20B	0.97
O1—P—C1	96.7 (2)	C22—C21—C24	101.2 (4)
O1—P—S2	110.16 (16)	C16—C22—C26	118.6 (4)
C1—P—S2	111.1 (2)	C16—C22—C21	115.8 (4)
O1—P—S1	110.86 (17)	C26—C22—C21	104.6 (4)
C1—P—S1	110.9 (2)	C16—C22—H22	105.6
S2—P—S1	115.52 (11)	C26—C22—H22	105.6
C39—N—C35	114.9 (5)	C21—C22—H22	105.6
C39—N—C37	110.4 (6)	C21—C23—H23A	109.5
C35—N—C37	112.8 (5)	C21—C23—H23B	109.5
C39—N—H1	111 (4)	H23A—C23—H23B	109.5
C35—N—H1	105 (4)	C21—C23—H23C	109.5
C37—N—H1	102 (4)	H23A—C23—H23C	109.5
C8—O1—P	122.8 (3)	H23B—C23—H23C	109.5
C4—O2—C7	117.4 (6)	C27—C24—C21	120.5 (4)
C2—C1—C6	118.4 (6)	C27—C24—C25	112.0 (4)
C2—C1—P	122.6 (5)	C21—C24—C25	103.2 (4)
C6—C1—P	119.0 (5)	C27—C24—H24	106.8
C1—C2—C3	119.6 (7)	C21—C24—H24	106.8
C1—C2—H2	120.2	C25—C24—H24	106.8
C3—C2—H2	120.2	C26—C25—C24	107.9 (4)
C4—C3—C2	120.4 (7)	C26—C25—H25A	110.1
C4—C3—H3	119.8	C24—C25—H25A	110.1
C2—C3—H3	119.8	C26—C25—H25B	110.1
C3—C4—C5	120.3 (7)	C24—C25—H25B	110.1
C3—C4—O2	114.3 (7)	H25A—C25—H25B	108.4
C5—C4—O2	125.4 (7)	C22—C26—C25	103.5 (4)
C4—C5—C6	119.5 (7)	C22—C26—H26A	111.1
C4—C5—H5	120.2	C25—C26—H26A	111.1
C6—C5—H5	120.2	C22—C26—H26B	111.1
C5—C6—C1	121.7 (6)	C25—C26—H26B	111.1
C5—C6—H6	119.2	H26A—C26—H26B	109
C1—C6—H6	119.2	C29—C27—C28	111.2 (5)
O2—C7—H7A	109.5	C29—C27—C24	109.7 (5)
O2—C7—H7B	109.5	C28—C27—C24	113.5 (5)
H7A—C7—H7B	109.5	C29—C27—H27	107.4
O2—C7—H7C	109.5	C28—C27—H27	107.4
H7A—C7—H7C	109.5	C24—C27—H27	107.4
H7B—C7—H7C	109.5	C27—C28—H28A	109.5
O1—C8—C9	108.2 (5)	C27—C28—H28B	109.5
O1—C8—C13	109.0 (4)	H28A—C28—H28B	109.5
C9—C8—C13	111.9 (5)	C27—C28—H28C	109.5
O1—C8—H8	109.2	H28A—C28—H28C	109.5
C9—C8—H8	109.2	H28B—C28—H28C	109.5
C13—C8—H8	109.2	C27—C29—C30	118.7 (5)
C8—C9—C10	108.7 (5)	C27—C29—H29A	107.6
C8—C9—H9A	109.9	C30—C29—H29A	107.6
C10—C9—H9A	109.9	C27—C29—H29B	107.6
C8—C9—H9B	109.9	C30—C29—H29B	107.6
C10—C9—H9B	109.9	H29A—C29—H29B	107.1
H9A—C9—H9B	108.3	C31—C30—C29	112.2 (5)
C9—C10—C11	114.2 (5)	C31—C30—H30A	109.2
C9—C10—H10A	108.7	C29—C30—H30A	109.2
C11—C10—H10A	108.7	C31—C30—H30B	109.2
C9—C10—H10B	108.7	C29—C30—H30B	109.2
C11—C10—H10B	108.7	H30A—C30—H30B	107.9
H10A—C10—H10B	107.6	C32—C31—C30	117.5 (7)
C14—C11—C12	109.3 (5)	C32—C31—H31A	107.9
C14—C11—C10	110.9 (5)	C30—C31—H31A	107.9
C12—C11—C10	107.0 (5)	C32—C31—H31B	107.9
C14—C11—C15	111.9 (4)	C30—C31—H31B	107.9
C12—C11—C15	109.6 (4)	H31A—C31—H31B	107.2
C10—C11—C15	108.0 (5)	C31—C32—C33	113.1 (7)
C18—C12—C13	121.1 (5)	C31—C32—C34	110.9 (7)
C18—C12—C11	123.1 (5)	C33—C32—C34	110.8 (6)
C13—C12—C11	115.8 (5)	C31—C32—H32	107.3
C8—C13—C12	112.3 (5)	C33—C32—H32	107.3
C8—C13—H13A	109.1	C34—C32—H32	107.3
C12—C13—H13A	109.1	C32—C33—H33A	109.5
C8—C13—H13B	109.1	C32—C33—H33B	109.5
C12—C13—H13B	109.1	H33A—C33—H33B	109.5
H13A—C13—H13B	107.9	C32—C33—H33C	109.5
C11—C14—H14A	109.5	H33A—C33—H33C	109.5
C11—C14—H14B	109.5	H33B—C33—H33C	109.5
H14A—C14—H14B	109.5	C32—C34—H34A	109.5
C11—C14—H14C	109.5	C32—C34—H34B	109.5
H14A—C14—H14C	109.5	H34A—C34—H34B	109.5
H14B—C14—H14C	109.5	C32—C34—H34C	109.5
C16—C15—C19	110.3 (4)	H34A—C34—H34C	109.5
C16—C15—C11	113.1 (4)	H34B—C34—H34C	109.5
C19—C15—C11	113.1 (4)	N—C35—C36	113.5 (6)
C16—C15—H15	106.6	N—C35—H35A	108.9
C19—C15—H15	106.6	C36—C35—H35A	108.9
C11—C15—H15	106.6	N—C35—H35B	108.9
C17—C16—C22	111.3 (4)	C36—C35—H35B	108.9
C17—C16—C15	111.1 (4)	H35A—C35—H35B	107.7
C22—C16—C15	109.0 (4)	C35—C36—H36A	109.5
C17—C16—H16	108.5	C35—C36—H36B	109.5
C22—C16—H16	108.5	H36A—C36—H36B	109.5
C15—C16—H16	108.5	C35—C36—H36C	109.5
C18—C17—C16	113.1 (5)	H36A—C36—H36C	109.5
C18—C17—H17A	108.9	H36B—C36—H36C	109.5
C16—C17—H17A	108.9	C38—C37—N	114.6 (6)
C18—C17—H17B	108.9	C38—C37—H37A	108.6
C16—C17—H17B	108.9	N—C37—H37A	108.6
H17A—C17—H17B	107.8	C38—C37—H37B	108.6
C12—C18—C17	125.6 (5)	N—C37—H37B	108.6
C12—C18—H18	117.2	H37A—C37—H37B	107.6
C17—C18—H18	117.2	C37—C38—H38A	109.5
C20—C19—C15	114.7 (4)	C37—C38—H38B	109.5
C20—C19—H19A	108.6	H38A—C38—H38B	109.5
C15—C19—H19A	108.6	C37—C38—H38C	109.5
C20—C19—H19B	108.6	H38A—C38—H38C	109.5
C15—C19—H19B	108.6	H38B—C38—H38C	109.5
H19A—C19—H19B	107.6	N—C39—C40	112.3 (7)
C19—C20—C21	112.3 (5)	N—C39—H39A	109.1
C19—C20—H20A	109.1	C40—C39—H39A	109.1
C21—C20—H20A	109.1	N—C39—H39B	109.1
C19—C20—H20B	109.1	C40—C39—H39B	109.1
C21—C20—H20B	109.1	H39A—C39—H39B	107.9
H20A—C20—H20B	107.9	C39—C40—H40A	109.5
C20—C21—C23	110.8 (5)	C39—C40—H40B	109.5
C20—C21—C22	105.5 (4)	H40A—C40—H40B	109.5
C23—C21—C22	112.1 (5)	C39—C40—H40C	109.5
C20—C21—C24	116.8 (5)	H40A—C40—H40C	109.5
C23—C21—C24	110.1 (4)	H40B—C40—H40C	109.5
C1—P—O1—C8	−157.5 (4)	C22—C16—C17—C18	−161.6 (5)
S2—P—O1—C8	−42.0 (4)	C15—C16—C17—C18	−40.0 (7)
S1—P—O1—C8	87.1 (4)	C13—C12—C18—C17	−178.1 (6)
O1—P—C1—C2	−116.5 (6)	C11—C12—C18—C17	−0.9 (11)
S2—P—C1—C2	128.9 (5)	C16—C17—C18—C12	12.8 (9)
S1—P—C1—C2	−1.1 (6)	C16—C15—C19—C20	50.7 (7)
O1—P—C1—C6	63.4 (5)	C11—C15—C19—C20	178.5 (5)
S2—P—C1—C6	−51.3 (5)	C15—C19—C20—C21	−53.6 (7)
S1—P—C1—C6	178.7 (4)	C19—C20—C21—C23	−67.2 (6)
C6—C1—C2—C3	−2.0 (10)	C19—C20—C21—C22	54.3 (6)
P—C1—C2—C3	177.9 (6)	C19—C20—C21—C24	165.7 (5)
C1—C2—C3—C4	1.8 (13)	C17—C16—C22—C26	−50.9 (7)
C2—C3—C4—C5	0.4 (13)	C15—C16—C22—C26	−173.7 (5)
C2—C3—C4—O2	178.9 (7)	C17—C16—C22—C21	−176.4 (5)
C7—O2—C4—C3	−179.9 (8)	C15—C16—C22—C21	60.7 (6)
C7—O2—C4—C5	−1.5 (12)	C20—C21—C22—C16	−60.7 (6)
C3—C4—C5—C6	−2.4 (11)	C23—C21—C22—C16	59.9 (6)
O2—C4—C5—C6	179.3 (6)	C24—C21—C22—C16	177.2 (5)
C4—C5—C6—C1	2.2 (9)	C20—C21—C22—C26	166.9 (5)
C2—C1—C6—C5	0.0 (9)	C23—C21—C22—C26	−72.5 (5)
P—C1—C6—C5	−179.9 (5)	C24—C21—C22—C26	44.8 (5)
P—O1—C8—C9	120.6 (5)	C20—C21—C24—C27	82.4 (6)
P—O1—C8—C13	−117.5 (5)	C23—C21—C24—C27	−45.1 (7)
O1—C8—C9—C10	177.3 (5)	C22—C21—C24—C27	−163.8 (5)
C13—C8—C9—C10	57.2 (7)	C20—C21—C24—C25	−151.9 (5)
C8—C9—C10—C11	−59.0 (7)	C23—C21—C24—C25	80.7 (5)
C9—C10—C11—C14	−65.7 (6)	C22—C21—C24—C25	−38.0 (5)
C9—C10—C11—C12	53.5 (7)	C27—C24—C25—C26	149.7 (5)
C9—C10—C11—C15	171.4 (5)	C21—C24—C25—C26	18.6 (6)
C14—C11—C12—C18	−106.3 (7)	C16—C22—C26—C25	−163.8 (5)
C10—C11—C12—C18	133.5 (6)	C21—C22—C26—C25	−33.0 (6)
C15—C11—C12—C18	16.7 (9)	C24—C25—C26—C22	8.6 (6)
C14—C11—C12—C13	71.1 (6)	C21—C24—C27—C29	−179.0 (5)
C10—C11—C12—C13	−49.1 (7)	C25—C24—C27—C29	59.4 (6)
C15—C11—C12—C13	−166.0 (5)	C21—C24—C27—C28	−54.0 (7)
O1—C8—C13—C12	−173.7 (5)	C25—C24—C27—C28	−175.6 (5)
C9—C8—C13—C12	−54.1 (7)	C28—C27—C29—C30	60.0 (7)
C18—C12—C13—C8	−131.3 (6)	C24—C27—C29—C30	−173.6 (5)
C11—C12—C13—C8	51.3 (7)	C27—C29—C30—C31	174.5 (6)
C14—C11—C15—C16	76.9 (6)	C29—C30—C31—C32	174.9 (6)
C12—C11—C15—C16	−44.6 (7)	C30—C31—C32—C33	−66.0 (9)
C10—C11—C15—C16	−160.8 (5)	C30—C31—C32—C34	168.9 (6)
C14—C11—C15—C19	−49.4 (7)	C39—N—C35—C36	61.5 (8)
C12—C11—C15—C19	−170.9 (5)	C37—N—C35—C36	−66.2 (8)
C10—C11—C15—C19	72.9 (6)	C39—N—C37—C38	173.5 (7)
C19—C15—C16—C17	−174.3 (5)	C35—N—C37—C38	−56.5 (8)
C11—C15—C16—C17	57.9 (6)	C35—N—C39—C40	58.3 (8)
C19—C15—C16—C22	−51.4 (6)	C37—N—C39—C40	−172.8 (6)
C11—C15—C16—C22	−179.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1···S1i	0.96 (7)	2.53 (7)	3.426 (7)	156 (5)
N—H1···S2i	0.96 (7)	2.78 (7)	3.437 (6)	126 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H1⋯S1i	0.96 (7)	2.53 (7)	3.426 (7)	156 (5)
N—H1⋯S2i	0.96 (7)	2.78 (7)	3.437 (6)	126 (5)

Symmetry code: (i) .