{Dimeth-yl [(phenyl-sulfon-yl)amido-]phosphato-κ(2) O,O'}bis-(tri-phenylphosphane-κP)copper(I).

In the title complex, [Cu(C8H11NO5PS)(C18H15P)2], the Cu(I) ion is coordinated by two tri-phenyl-phosphane mol-ecules and two O atoms of the chelating dimeth-yl(phenyl-sulfon-yl)amido-phosphate anion, generating a squashed CuO2P2 tetrahedron. In the six-membered chelate ring, the Cu, P and O atoms are almost coplanar (r.m.s. deviation = 0.024 Å), with the N and S atoms displaced in the same direction, by 0.708 (5) and 0.429 (2) Å, respectively.

Related literature

For the synthesis of sulfonyl­amide derivatives, see: Kirsanov (1965 ▶); Moroz et al. (2012 ▶). For details of the pharmacological and biological properties of sulfonyl­amide derivatives, see: Kishino & Saito (1979 ▶); Xu & Angell (2000 ▶). For CuI-containing complexes with tri­phenyl­phosphane, see: Barron et al. (1987 ▶); Yang et al. (2001 ▶); Zabirov et al. (2003 ▶). For details of potential applications of CuI-containing complexes, see: Nagashima et al. (1993 ▶); Nondek et al. (1987 ▶); Tarkhanova et al. (2001 ▶); Zazybin et al. (2006 ▶); Verat et al. (2006 ▶). For coord­ination compounds of 3d metals with sulfonylamidophosphate ligands, see: Moroz et al. (2009 ▶); Trush et al. (2011 ▶). For the coordination mode of structural analogs of β-diketones, see: Gawryszewska et al. (2011 ▶); Yizhak et al. (2013 ▶); Kariaka et al. (2013 ▶); Amirkhanov et al. (2014 ▶).

Experimental

Crystal data

[Cu(C8H11NO5PS)(C18H15P)2]

M = 852.29

Monoclinic,

a = 12.8657 (12) Å

b = 26.281 (3) Å

c = 13.971 (3) Å

β = 121.875 (10)°

V = 4011.6 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 100 K

0.40 × 0.30 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.74, T max = 0.90

27134 measured reflections

9293 independent reflections

4739 reflections with I > 2σ(I)

R int = 0.137

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.120

S = 1.04

9293 reflections

438 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.56 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, cusp. DOI: 10.1107/S1600536814010095/hb7222sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010095/hb7222Isup2.hkl

CCDC reference: 1000731

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Cu(C8H11NO5PS)(C18H15P)2]	F(000) = 1768
Mr = 852.29	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8657 (12) Å	Cell parameters from 27134 reflections
b = 26.281 (3) Å	θ = 2.9–28.5°
c = 13.971 (3) Å	µ = 0.76 mm−1
β = 121.875 (10)°	T = 100 K
V = 4011.6 (11) Å3	Needle, colourless
Z = 4	0.40 × 0.30 × 0.10 mm

Nonius KappaCCD diffractometer	9293 independent reflections
Radiation source: sealed X-ray tube	4739 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm-1	Rint = 0.137
φ scans and ω scans with κ offset	θmax = 28.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→16
Tmin = 0.74, Tmax = 0.90	k = −33→34
27134 measured reflections	l = −18→18

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.086	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0188P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
9293 reflections	Δρmax = 0.48 e Å−3
438 parameters	Δρmin = −0.56 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 > 2σ(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	0.7620 (4)	0.16461 (19)	1.0173 (4)	0.0134 (12)
C2	0.7765 (5)	0.15558 (19)	0.9275 (4)	0.0195 (13)
H68	0.7094	0.1479	0.8566	0.023*
C3	0.8930 (5)	0.1582 (2)	0.9452 (5)	0.0257 (14)
H102	0.9034	0.1531	0.8848	0.031*
C4	0.9933 (5)	0.1682 (2)	1.0499 (5)	0.0260 (14)
H106	1.0707	0.1698	1.0602	0.031*
C5	0.9789 (5)	0.1758 (2)	1.1401 (5)	0.0323 (16)
H19	1.0468	0.1822	1.2115	0.039*
C6	0.8614 (5)	0.1740 (2)	1.1237 (5)	0.0277 (15)
H57	0.8509	0.1790	1.1840	0.033*
C7	0.3285 (5)	0.2987 (2)	0.8180 (5)	0.0375 (17)
H74A	0.2652	0.2749	0.7708	0.056*
H74B	0.3002	0.3327	0.7928	0.056*
H74C	0.3493	0.2948	0.8945	0.056*
C8	0.6702 (5)	0.2749 (2)	0.8269 (5)	0.0303 (15)
H7A	0.6423	0.3079	0.8330	0.045*
H7B	0.7084	0.2774	0.7838	0.045*
H7C	0.7283	0.2622	0.9008	0.045*
C9	0.2961 (5)	0.06859 (19)	0.5000 (4)	0.0203 (5)
C10	0.1706 (5)	0.06746 (19)	0.4622 (4)	0.0203 (5)
H25	0.1469	0.0701	0.5144	0.024*
C11	0.0819 (5)	0.06245 (18)	0.3490 (4)	0.0203 (5)
H21	−0.0003	0.0612	0.3260	0.024*
C12	0.1160 (5)	0.05931 (19)	0.2692 (4)	0.0203 (5)
H16	0.0567	0.0560	0.1930	0.024*
C13	0.2384 (5)	0.06113 (19)	0.3045 (4)	0.0203 (5)
H15	0.2613	0.0599	0.2515	0.024*
C14	0.3274 (5)	0.06484 (19)	0.4179 (4)	0.0203 (5)
H35	0.4095	0.0648	0.4403	0.024*
C15	0.4477 (4)	0.00831 (18)	0.6988 (4)	0.0132 (12)
C16	0.4271 (4)	−0.03269 (19)	0.6270 (4)	0.0147 (12)
H20	0.3927	−0.0268	0.5504	0.018*
C17	0.4570 (5)	−0.0819 (2)	0.6678 (5)	0.0189 (13)
H6	0.4437	−0.1088	0.6192	0.023*
C18	0.5070 (5)	−0.0910 (2)	0.7817 (5)	0.0215 (14)
H56	0.5264	−0.1241	0.8093	0.026*
C19	0.5283 (5)	−0.0510 (2)	0.8547 (5)	0.0242 (14)
H8	0.5628	−0.0573	0.9311	0.029*
C20	0.4987 (5)	−0.0024 (2)	0.8145 (5)	0.0236 (14)
H31	0.5123	0.0241	0.8640	0.028*
C21	0.5434 (5)	0.09651 (19)	0.6489 (4)	0.0141 (12)
C22	0.6453 (5)	0.0664 (2)	0.6779 (4)	0.0184 (13)
H60	0.6493	0.0333	0.7032	0.022*
C23	0.7411 (5)	0.0854 (2)	0.6694 (4)	0.0229 (14)
H29	0.8085	0.0650	0.6888	0.027*
C24	0.7358 (5)	0.1347 (2)	0.6320 (4)	0.0243 (14)
H54	0.7988	0.1472	0.6245	0.029*
C25	0.6370 (5)	0.1655 (2)	0.6057 (4)	0.0191 (13)
H70	0.6346	0.1988	0.5822	0.023*
C26	0.5425 (5)	0.14690 (19)	0.6142 (4)	0.0191 (13)
H67	0.4767	0.1680	0.5966	0.023*
C27	0.1898 (4)	0.0599 (2)	0.8496 (4)	0.0177 (13)
C28	0.1400 (5)	0.0630 (2)	0.9169 (4)	0.0232 (14)
H105	0.1078	0.0938	0.9224	0.028*
C29	0.1375 (5)	0.0207 (2)	0.9761 (5)	0.0324 (16)
H1	0.1021	0.0229	1.0193	0.039*
C30	0.1891 (5)	−0.0249 (2)	0.9696 (5)	0.0332 (16)
H45	0.1901	−0.0531	1.0104	0.040*
C31	0.2386 (5)	−0.0284 (2)	0.9029 (5)	0.0285 (15)
H72	0.2710	−0.0591	0.8975	0.034*
C32	0.2400 (5)	0.01393 (19)	0.8440 (4)	0.0209 (14)
H38	0.2748	0.0115	0.8003	0.025*
C33	0.0584 (4)	0.11361 (19)	0.6394 (4)	0.0143 (12)
C34	0.0297 (5)	0.1559 (2)	0.5668 (4)	0.0191 (13)
H61	0.0792	0.1847	0.5923	0.023*
C35	−0.0716 (5)	0.1547 (2)	0.4583 (5)	0.0251 (15)
H107	−0.0912	0.1832	0.4124	0.030*
C36	−0.1443 (5)	0.1115 (2)	0.4168 (5)	0.0275 (15)
H47	−0.2106	0.1104	0.3429	0.033*
C37	−0.1168 (5)	0.0703 (2)	0.4865 (5)	0.0275 (15)
H66	−0.1659	0.0415	0.4594	0.033*
C38	−0.0173 (5)	0.0709 (2)	0.5966 (4)	0.0194 (13)
H62	−0.0008	0.0425	0.6423	0.023*
C39	0.1906 (5)	0.1685 (2)	0.8525 (5)	0.0235 (6)
C40	0.0861 (5)	0.19774 (19)	0.8175 (5)	0.0235 (6)
H13	0.0132	0.1899	0.7510	0.028*
C41	0.0923 (5)	0.2386 (2)	0.8830 (4)	0.0235 (6)
H28	0.0230	0.2585	0.8589	0.028*
C42	0.1968 (5)	0.2504 (2)	0.9812 (5)	0.0235 (6)
H65	0.1984	0.2777	1.0242	0.028*
C43	0.3019 (5)	0.2214 (2)	1.0173 (5)	0.0235 (6)
H14	0.3742	0.2291	1.0845	0.028*
C44	0.2972 (5)	0.1810 (2)	0.9521 (4)	0.0235 (6)
H75	0.3673	0.1617	0.9757	0.028*
Cu1	0.36062 (6)	0.12135 (2)	0.75302 (5)	0.01638 (18)
N1	0.5554 (4)	0.21783 (15)	0.9479 (3)	0.0169 (10)
O1	0.5448 (3)	0.12269 (13)	0.9166 (3)	0.0198 (9)
O2	0.6296 (3)	0.15752 (13)	1.1063 (3)	0.0246 (9)
O3	0.3780 (3)	0.19846 (12)	0.7364 (3)	0.0173 (9)
O4	0.4335 (3)	0.28906 (12)	0.8119 (3)	0.0268 (10)
O5	0.5671 (3)	0.24042 (13)	0.7711 (3)	0.0227 (9)
P1	0.48025 (13)	0.23250 (5)	0.81736 (13)	0.0190 (4)
P2	0.41040 (12)	0.07398 (5)	0.65026 (12)	0.0153 (3)
P3	0.20168 (12)	0.11467 (5)	0.77600 (12)	0.0162 (3)
S1	0.61185 (12)	0.16414 (5)	0.99649 (12)	0.0183 (3)

	U11	U22	U33	U12	U13	U23
C1	0.008 (3)	0.014 (3)	0.015 (3)	0.000 (2)	0.004 (3)	0.003 (2)
C2	0.022 (4)	0.019 (3)	0.018 (3)	−0.001 (3)	0.011 (3)	−0.001 (3)
C3	0.034 (4)	0.026 (3)	0.026 (4)	0.003 (3)	0.022 (3)	0.001 (3)
C4	0.015 (3)	0.032 (4)	0.027 (4)	0.002 (3)	0.008 (3)	0.001 (3)
C5	0.021 (4)	0.045 (4)	0.023 (4)	−0.007 (3)	0.006 (3)	−0.013 (3)
C6	0.022 (4)	0.042 (4)	0.021 (4)	0.000 (3)	0.013 (3)	−0.002 (3)
C7	0.029 (4)	0.025 (4)	0.067 (5)	0.002 (3)	0.031 (4)	−0.005 (3)
C8	0.025 (4)	0.027 (4)	0.041 (4)	−0.007 (3)	0.020 (3)	0.008 (3)
C9	0.0184 (14)	0.0199 (12)	0.0188 (14)	0.0008 (11)	0.0072 (12)	−0.0007 (11)
C10	0.0184 (14)	0.0199 (12)	0.0188 (14)	0.0008 (11)	0.0072 (12)	−0.0007 (11)
C11	0.0184 (14)	0.0199 (12)	0.0188 (14)	0.0008 (11)	0.0072 (12)	−0.0007 (11)
C12	0.0184 (14)	0.0199 (12)	0.0188 (14)	0.0008 (11)	0.0072 (12)	−0.0007 (11)
C13	0.0184 (14)	0.0199 (12)	0.0188 (14)	0.0008 (11)	0.0072 (12)	−0.0007 (11)
C14	0.0184 (14)	0.0199 (12)	0.0188 (14)	0.0008 (11)	0.0072 (12)	−0.0007 (11)
C15	0.011 (3)	0.010 (3)	0.022 (3)	0.000 (2)	0.011 (3)	−0.004 (2)
C16	0.012 (3)	0.020 (3)	0.014 (3)	−0.002 (2)	0.008 (3)	0.002 (3)
C17	0.018 (3)	0.018 (3)	0.027 (4)	−0.005 (3)	0.016 (3)	−0.006 (3)
C18	0.020 (3)	0.019 (3)	0.028 (4)	0.004 (3)	0.015 (3)	0.002 (3)
C19	0.019 (3)	0.029 (4)	0.013 (3)	0.002 (3)	0.000 (3)	0.002 (3)
C20	0.025 (4)	0.021 (3)	0.017 (3)	0.002 (3)	0.005 (3)	−0.003 (3)
C21	0.012 (3)	0.018 (3)	0.010 (3)	−0.004 (2)	0.005 (3)	−0.008 (2)
C22	0.019 (3)	0.015 (3)	0.026 (4)	−0.001 (3)	0.016 (3)	−0.003 (3)
C23	0.016 (3)	0.024 (3)	0.028 (4)	0.001 (3)	0.011 (3)	−0.006 (3)
C24	0.027 (4)	0.030 (4)	0.022 (3)	−0.013 (3)	0.017 (3)	−0.007 (3)
C25	0.023 (4)	0.021 (3)	0.018 (3)	−0.010 (3)	0.015 (3)	−0.005 (3)
C26	0.020 (3)	0.015 (3)	0.021 (3)	−0.004 (3)	0.010 (3)	−0.003 (3)
C27	0.011 (3)	0.021 (3)	0.017 (3)	−0.004 (3)	0.005 (3)	0.000 (3)
C28	0.020 (3)	0.024 (3)	0.025 (4)	−0.002 (3)	0.011 (3)	0.006 (3)
C29	0.028 (4)	0.037 (4)	0.031 (4)	−0.014 (3)	0.014 (3)	−0.001 (3)
C30	0.033 (4)	0.024 (4)	0.025 (4)	−0.007 (3)	0.004 (3)	0.015 (3)
C31	0.023 (4)	0.021 (4)	0.033 (4)	−0.003 (3)	0.009 (3)	0.000 (3)
C32	0.013 (3)	0.017 (3)	0.017 (3)	−0.001 (3)	−0.002 (3)	0.004 (3)
C33	0.013 (3)	0.015 (3)	0.018 (3)	0.000 (2)	0.011 (3)	−0.002 (3)
C34	0.010 (3)	0.027 (3)	0.025 (4)	−0.003 (3)	0.012 (3)	0.002 (3)
C35	0.019 (4)	0.032 (4)	0.029 (4)	0.006 (3)	0.015 (3)	0.007 (3)
C36	0.011 (3)	0.045 (4)	0.023 (4)	−0.002 (3)	0.007 (3)	−0.003 (3)
C37	0.023 (4)	0.026 (4)	0.035 (4)	−0.002 (3)	0.016 (3)	−0.006 (3)
C38	0.013 (3)	0.024 (3)	0.019 (3)	0.000 (3)	0.008 (3)	0.000 (3)
C39	0.0276 (15)	0.0243 (14)	0.0243 (15)	0.0026 (12)	0.0176 (13)	−0.0019 (11)
C40	0.0276 (15)	0.0243 (14)	0.0243 (15)	0.0026 (12)	0.0176 (13)	−0.0019 (11)
C41	0.0276 (15)	0.0243 (14)	0.0243 (15)	0.0026 (12)	0.0176 (13)	−0.0019 (11)
C42	0.0276 (15)	0.0243 (14)	0.0243 (15)	0.0026 (12)	0.0176 (13)	−0.0019 (11)
C43	0.0276 (15)	0.0243 (14)	0.0243 (15)	0.0026 (12)	0.0176 (13)	−0.0019 (11)
C44	0.0276 (15)	0.0243 (14)	0.0243 (15)	0.0026 (12)	0.0176 (13)	−0.0019 (11)
Cu1	0.0157 (4)	0.0148 (4)	0.0206 (4)	−0.0015 (3)	0.0109 (3)	−0.0025 (3)
N1	0.025 (3)	0.009 (2)	0.017 (3)	−0.002 (2)	0.012 (2)	−0.004 (2)
O1	0.016 (2)	0.016 (2)	0.021 (2)	−0.0027 (18)	0.0045 (18)	−0.0015 (18)
O2	0.027 (2)	0.030 (2)	0.019 (2)	−0.0022 (19)	0.014 (2)	0.0023 (19)
O3	0.014 (2)	0.012 (2)	0.024 (2)	−0.0024 (17)	0.0090 (19)	0.0023 (17)
O4	0.024 (2)	0.012 (2)	0.041 (3)	0.0049 (18)	0.016 (2)	0.0027 (19)
O5	0.021 (2)	0.022 (2)	0.028 (2)	−0.0081 (18)	0.015 (2)	−0.0018 (19)
P1	0.0175 (9)	0.0135 (8)	0.0252 (9)	−0.0002 (7)	0.0108 (8)	0.0006 (7)
P2	0.0143 (8)	0.0137 (8)	0.0186 (9)	−0.0004 (6)	0.0093 (7)	−0.0005 (7)
P3	0.0144 (8)	0.0150 (8)	0.0211 (8)	−0.0007 (7)	0.0106 (7)	−0.0002 (7)
S1	0.0198 (9)	0.0175 (8)	0.0189 (8)	−0.0015 (7)	0.0110 (7)	0.0002 (7)

C1—C6	1.378 (7)	C24—H54	0.9300
C1—C2	1.384 (6)	C25—C26	1.373 (6)
C1—S1	1.795 (5)	C25—H70	0.9300
C2—C3	1.386 (7)	C26—H67	0.9300
C2—H68	0.9300	C27—C28	1.392 (6)
C3—C4	1.371 (7)	C27—C32	1.392 (7)
C3—H102	0.9300	C27—P3	1.821 (5)
C4—C5	1.381 (7)	C28—C29	1.396 (7)
C4—H106	0.9300	C28—H105	0.9300
C5—C6	1.405 (7)	C29—C30	1.396 (7)
C5—H19	0.9300	C29—H1	0.9300
C6—H57	0.9300	C30—C31	1.382 (7)
C7—O4	1.419 (5)	C30—H45	0.9300
C7—H74A	0.9600	C31—C32	1.390 (7)
C7—H74B	0.9600	C31—H72	0.9300
C7—H74C	0.9600	C32—H38	0.9300
C8—O5	1.448 (5)	C33—C38	1.397 (6)
C8—H7A	0.9600	C33—C34	1.416 (6)
C8—H7B	0.9600	C33—P3	1.824 (5)
C8—H7C	0.9600	C34—C35	1.382 (7)
C9—C14	1.406 (6)	C34—H61	0.9300
C9—C10	1.409 (6)	C35—C36	1.390 (7)
C9—P2	1.824 (5)	C35—H107	0.9300
C10—C11	1.383 (6)	C36—C37	1.370 (7)
C10—H25	0.9300	C36—H47	0.9300
C11—C12	1.400 (6)	C37—C38	1.387 (7)
C11—H21	0.9300	C37—H66	0.9300
C12—C13	1.380 (6)	C38—H62	0.9300
C12—H16	0.9300	C39—C44	1.382 (7)
C13—C14	1.384 (6)	C39—C40	1.394 (7)
C13—H15	0.9300	C39—P3	1.823 (5)
C14—H35	0.9300	C40—C41	1.386 (7)
C15—C16	1.399 (6)	C40—H13	0.9300
C15—C20	1.415 (7)	C41—C42	1.355 (7)
C15—P2	1.824 (5)	C41—H28	0.9300
C16—C17	1.385 (6)	C42—C43	1.394 (6)
C16—H20	0.9300	C42—H65	0.9300
C17—C18	1.386 (7)	C43—C44	1.380 (7)
C17—H6	0.9300	C43—H14	0.9300
C18—C19	1.388 (7)	C44—H75	0.9300
C18—H56	0.9300	Cu1—O3	2.065 (3)
C19—C20	1.366 (7)	Cu1—O1	2.263 (3)
C19—H8	0.9300	Cu1—P2	2.2345 (15)
C20—H31	0.9300	Cu1—P3	2.2381 (14)
C21—C22	1.395 (6)	N1—S1	1.568 (4)
C21—C26	1.409 (6)	N1—P1	1.596 (4)
C21—P2	1.820 (5)	O1—S1	1.470 (3)
C22—C23	1.391 (6)	O2—S1	1.438 (3)
C22—H60	0.9300	O3—P1	1.496 (3)
C23—C24	1.386 (7)	O4—P1	1.590 (3)
C23—H29	0.9300	O5—P1	1.572 (3)
C24—C25	1.382 (7)
C6—C1—C2	121.0 (5)	C27—C28—C29	121.1 (5)
C6—C1—S1	118.9 (4)	C27—C28—H105	119.5
C2—C1—S1	120.1 (4)	C29—C28—H105	119.5
C1—C2—C3	118.8 (5)	C28—C29—C30	119.0 (5)
C1—C2—H68	120.6	C28—C29—H1	120.5
C3—C2—H68	120.6	C30—C29—H1	120.5
C4—C3—C2	121.2 (5)	C31—C30—C29	120.3 (5)
C4—C3—H102	119.4	C31—C30—H45	119.8
C2—C3—H102	119.4	C29—C30—H45	119.8
C3—C4—C5	119.9 (5)	C30—C31—C32	120.1 (5)
C3—C4—H106	120.1	C30—C31—H72	120.0
C5—C4—H106	120.1	C32—C31—H72	120.0
C4—C5—C6	119.8 (6)	C31—C32—C27	120.7 (5)
C4—C5—H19	120.1	C31—C32—H38	119.7
C6—C5—H19	120.1	C27—C32—H38	119.7
C1—C6—C5	119.2 (5)	C38—C33—C34	117.7 (5)
C1—C6—H57	120.4	C38—C33—P3	123.5 (4)
C5—C6—H57	120.4	C34—C33—P3	118.3 (4)
O4—C7—H74A	109.5	C35—C34—C33	120.4 (5)
O4—C7—H74B	109.5	C35—C34—H61	119.8
H74A—C7—H74B	109.5	C33—C34—H61	119.8
O4—C7—H74C	109.5	C34—C35—C36	120.8 (5)
H74A—C7—H74C	109.5	C34—C35—H107	119.6
H74B—C7—H74C	109.5	C36—C35—H107	119.6
O5—C8—H7A	109.5	C37—C36—C35	119.0 (5)
O5—C8—H7B	109.5	C37—C36—H47	120.5
H7A—C8—H7B	109.5	C35—C36—H47	120.5
O5—C8—H7C	109.5	C36—C37—C38	121.3 (5)
H7A—C8—H7C	109.5	C36—C37—H66	119.3
H7B—C8—H7C	109.5	C38—C37—H66	119.3
C14—C9—C10	117.3 (5)	C37—C38—C33	120.6 (5)
C14—C9—P2	122.7 (4)	C37—C38—H62	119.7
C10—C9—P2	120.1 (4)	C33—C38—H62	119.7
C11—C10—C9	121.3 (5)	C44—C39—C40	118.9 (5)
C11—C10—H25	119.3	C44—C39—P3	115.5 (4)
C9—C10—H25	119.3	C40—C39—P3	125.6 (4)
C10—C11—C12	120.0 (5)	C41—C40—C39	119.2 (5)
C10—C11—H21	120.0	C41—C40—H13	120.4
C12—C11—H21	120.0	C39—C40—H13	120.4
C13—C12—C11	119.5 (5)	C42—C41—C40	121.7 (5)
C13—C12—H16	120.3	C42—C41—H28	119.1
C11—C12—H16	120.3	C40—C41—H28	119.1
C12—C13—C14	120.6 (5)	C41—C42—C43	119.7 (5)
C12—C13—H15	119.7	C41—C42—H65	120.1
C14—C13—H15	119.7	C43—C42—H65	120.1
C13—C14—C9	121.3 (5)	C44—C43—C42	119.0 (5)
C13—C14—H35	119.4	C44—C43—H14	120.5
C9—C14—H35	119.4	C42—C43—H14	120.5
C16—C15—C20	117.6 (5)	C43—C44—C39	121.5 (5)
C16—C15—P2	123.3 (4)	C43—C44—H75	119.3
C20—C15—P2	119.0 (4)	C39—C44—H75	119.3
C17—C16—C15	121.2 (5)	O3—Cu1—P2	112.93 (9)
C17—C16—H20	119.4	O3—Cu1—P3	104.75 (9)
C15—C16—H20	119.4	P2—Cu1—P3	129.95 (6)
C16—C17—C18	119.6 (5)	O3—Cu1—O1	88.88 (13)
C16—C17—H6	120.2	P2—Cu1—O1	98.93 (9)
C18—C17—H6	120.2	P3—Cu1—O1	113.89 (9)
C17—C18—C19	120.3 (5)	S1—N1—P1	125.1 (3)
C17—C18—H56	119.9	S1—O1—Cu1	131.3 (2)
C19—C18—H56	119.9	P1—O3—Cu1	127.3 (2)
C20—C19—C18	120.2 (5)	C7—O4—P1	120.7 (3)
C20—C19—H8	119.9	C8—O5—P1	120.7 (3)
C18—C19—H8	119.9	O3—P1—O5	107.5 (2)
C19—C20—C15	121.1 (5)	O3—P1—O4	111.3 (2)
C19—C20—H31	119.5	O5—P1—O4	100.9 (2)
C15—C20—H31	119.5	O3—P1—N1	118.7 (2)
C22—C21—C26	117.9 (5)	O5—P1—N1	111.6 (2)
C22—C21—P2	123.9 (4)	O4—P1—N1	105.4 (2)
C26—C21—P2	118.2 (4)	C21—P2—C15	104.3 (2)
C23—C22—C21	120.7 (5)	C21—P2—C9	101.8 (2)
C23—C22—H60	119.6	C15—P2—C9	104.4 (2)
C21—C22—H60	119.6	C21—P2—Cu1	114.54 (16)
C24—C23—C22	119.9 (5)	C15—P2—Cu1	113.38 (17)
C24—C23—H29	120.1	C9—P2—Cu1	116.87 (17)
C22—C23—H29	120.1	C27—P3—C39	103.1 (2)
C25—C24—C23	120.2 (5)	C27—P3—C33	103.8 (2)
C25—C24—H54	119.9	C39—P3—C33	106.1 (2)
C23—C24—H54	119.9	C27—P3—Cu1	119.89 (17)
C26—C25—C24	120.1 (5)	C39—P3—Cu1	112.55 (18)
C26—C25—H70	120.0	C33—P3—Cu1	110.26 (16)
C24—C25—H70	120.0	O2—S1—O1	114.8 (2)
C25—C26—C21	121.2 (5)	O2—S1—N1	110.3 (2)
C25—C26—H67	119.4	O1—S1—N1	112.7 (2)
C21—C26—H67	119.4	O2—S1—C1	106.1 (2)
C28—C27—C32	118.8 (5)	O1—S1—C1	106.2 (2)
C28—C27—P3	122.7 (4)	N1—S1—C1	106.1 (2)
C32—C27—P3	118.3 (4)
C6—C1—C2—C3	−2.7 (8)	Cu1—O3—P1—N1	−27.4 (3)
S1—C1—C2—C3	177.4 (4)	C8—O5—P1—O3	175.3 (3)
C1—C2—C3—C4	1.8 (8)	C8—O5—P1—O4	58.6 (4)
C2—C3—C4—C5	0.0 (8)	C8—O5—P1—N1	−53.0 (4)
C3—C4—C5—C6	−0.8 (9)	C7—O4—P1—O3	49.6 (4)
C2—C1—C6—C5	1.9 (8)	C7—O4—P1—O5	163.5 (4)
S1—C1—C6—C5	−178.2 (4)	C7—O4—P1—N1	−80.3 (4)
C4—C5—C6—C1	−0.1 (8)	S1—N1—P1—O3	49.7 (4)
C14—C9—C10—C11	0.5 (7)	S1—N1—P1—O5	−76.2 (3)
P2—C9—C10—C11	−178.8 (4)	S1—N1—P1—O4	175.1 (3)
C9—C10—C11—C12	−1.2 (8)	C22—C21—P2—C15	1.3 (5)
C10—C11—C12—C13	0.1 (8)	C26—C21—P2—C15	179.7 (4)
C11—C12—C13—C14	1.5 (8)	C22—C21—P2—C9	−107.1 (4)
C12—C13—C14—C9	−2.2 (8)	C26—C21—P2—C9	71.4 (4)
C10—C9—C14—C13	1.2 (8)	C22—C21—P2—Cu1	125.8 (4)
P2—C9—C14—C13	−179.6 (4)	C26—C21—P2—Cu1	−55.7 (4)
C20—C15—C16—C17	−0.8 (7)	C16—C15—P2—C21	−85.1 (4)
P2—C15—C16—C17	180.0 (4)	C20—C15—P2—C21	95.7 (4)
C15—C16—C17—C18	0.7 (7)	C16—C15—P2—C9	21.4 (5)
C16—C17—C18—C19	−0.7 (7)	C20—C15—P2—C9	−157.8 (4)
C17—C18—C19—C20	0.8 (8)	C16—C15—P2—Cu1	149.7 (4)
C18—C19—C20—C15	−0.9 (8)	C20—C15—P2—Cu1	−29.5 (4)
C16—C15—C20—C19	0.9 (8)	C14—C9—P2—C21	20.4 (5)
P2—C15—C20—C19	−179.9 (4)	C10—C9—P2—C21	−160.3 (4)
C26—C21—C22—C23	−1.8 (7)	C14—C9—P2—C15	−87.9 (5)
P2—C21—C22—C23	176.6 (4)	C10—C9—P2—C15	91.3 (4)
C21—C22—C23—C24	0.1 (8)	C14—C9—P2—Cu1	146.0 (4)
C22—C23—C24—C25	1.5 (8)	C10—C9—P2—Cu1	−34.8 (5)
C23—C24—C25—C26	−1.4 (8)	C28—C27—P3—C39	20.0 (5)
C24—C25—C26—C21	−0.3 (8)	C32—C27—P3—C39	−155.7 (4)
C22—C21—C26—C25	1.9 (7)	C28—C27—P3—C33	−90.5 (5)
P2—C21—C26—C25	−176.6 (4)	C32—C27—P3—C33	93.8 (4)
C32—C27—C28—C29	−1.4 (8)	C28—C27—P3—Cu1	146.0 (4)
P3—C27—C28—C29	−177.0 (4)	C32—C27—P3—Cu1	−29.7 (5)
C27—C28—C29—C30	1.7 (8)	C44—C39—P3—C27	80.6 (4)
C28—C29—C30—C31	−1.8 (8)	C40—C39—P3—C27	−100.9 (5)
C29—C30—C31—C32	1.6 (8)	C44—C39—P3—C33	−170.6 (4)
C30—C31—C32—C27	−1.2 (8)	C40—C39—P3—C33	7.9 (5)
C28—C27—C32—C31	1.1 (8)	C44—C39—P3—Cu1	−50.0 (4)
P3—C27—C32—C31	176.9 (4)	C40—C39—P3—Cu1	128.5 (4)
C38—C33—C34—C35	1.3 (7)	C38—C33—P3—C27	−17.6 (5)
P3—C33—C34—C35	173.5 (4)	C34—C33—P3—C27	170.6 (4)
C33—C34—C35—C36	−2.5 (7)	C38—C33—P3—C39	−125.8 (4)
C34—C35—C36—C37	2.2 (8)	C34—C33—P3—C39	62.4 (4)
C35—C36—C37—C38	−0.8 (8)	C38—C33—P3—Cu1	112.0 (4)
C36—C37—C38—C33	−0.3 (8)	C34—C33—P3—Cu1	−59.7 (4)
C34—C33—C38—C37	0.1 (7)	Cu1—O1—S1—O2	115.2 (3)
P3—C33—C38—C37	−171.7 (4)	Cu1—O1—S1—N1	−12.2 (3)
C44—C39—C40—C41	0.4 (7)	Cu1—O1—S1—C1	−127.9 (3)
P3—C39—C40—C41	−178.1 (4)	P1—N1—S1—O2	−157.4 (3)
C39—C40—C41—C42	−1.1 (8)	P1—N1—S1—O1	−27.6 (4)
C40—C41—C42—C43	1.0 (8)	P1—N1—S1—C1	88.2 (3)
C41—C42—C43—C44	−0.2 (8)	C6—C1—S1—O2	−18.7 (5)
C42—C43—C44—C39	−0.5 (8)	C2—C1—S1—O2	161.2 (4)
C40—C39—C44—C43	0.4 (8)	C6—C1—S1—O1	−141.2 (4)
P3—C39—C44—C43	179.0 (4)	C2—C1—S1—O1	38.7 (5)
Cu1—O3—P1—O5	100.4 (2)	C6—C1—S1—N1	98.7 (4)
Cu1—O3—P1—O4	−150.0 (2)	C2—C1—S1—N1	−81.5 (5)

Table 1

Selected bond lengths (Å)

Cu1—O3	2.065 (3)
Cu1—O1	2.263 (3)
Cu1—P2	2.2345 (15)
Cu1—P3	2.2381 (14)