Bis(dicyclo-hexyl-phenyl-phosphine)silver(I) nitrate.

The title compound, [Ag(C(18)H(27)P)(2)]NO(3), is a mononuclear salt species in which the Ag atom is coordinated by two phosphine ligands, forming a cation, with the nitrate as the counter-anion, weakly inter-acting with the Ag atom, resulting in Ag⋯O distances of 2.602 (6) and 2.679 (6) Å. The cationic silver-phosphine complex has a non-linear geometry in which the P-Ag-P angle is 154.662 (19)°. The Ag-P bond lengths are 2.4303 (6) and 2.4046 (5) Å.

Related literature

For a review of the chemistry of silver(I) complexes, see: Meijboom et al. (2009 ▶). For the coordination chemistry of AgX salts (X = F−, Cl−, Br−, I−, BF4 −, PF6 −, NO3 − etc) with group 15 donor ligands, with the main focus on tertiary phosphines and in their context as potential anti­tumor agents, see: Berners-Price et al. (1998 ▶); Liu et al. (2008 ▶). For two- and three-coordinate AgX (X = NO3 −) complexes/salts with bulky phosphine ligands, see: Bowmaker et al. (1996 ▶); Camalli & Caruso (1988 ▶); Fenske et al. (2007 ▶); for X = NO2, see: Cingolani et al. (2002 ▶); for X = Cl−, Br−, I−, CN−, SCN− and NCO-, see: Bowmaker et al. (1996 ▶); Bayler et al. (1996 ▶); and for two coordinate X = ClO4 -, see: Alyea et al. (1982 ▶, 2002 ▶); Baiada et al. (1990 ▶). For the solution behavior of [LAgX] complexes, see: Muetterties & Alegranti (1972 ▶). For atomic radii, see: Pauling (1960 ▶).

Experimental

Crystal data

[Ag(C18H27P)2]NO3

M = 718.61

Monoclinic,

a = 10.9207 (4) Å

b = 13.6312 (5) Å

c = 12.2121 (5) Å

β = 106.896 (1)°

V = 1739.45 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.71 mm−1

T = 296 K

0.42 × 0.34 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.756, T max = 0.908

19954 measured reflections

6614 independent reflections

6503 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.055

S = 1.06

6614 reflections

389 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 2322 Friedel pairs

Flack parameter: 0.041 (15)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 1997 ▶), PLATON (Spek, 2009 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011724/bg2336sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011724/bg2336Isup2.hkl

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

[Ag(C18H27P)2]NO3	F(000) = 756
Mr = 718.61	Dx = 1.372 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 19966 reflections
a = 10.9207 (4) Å	θ = 1.7–27.8°
b = 13.6312 (5) Å	µ = 0.71 mm−1
c = 12.2121 (5) Å	T = 296 K
β = 106.896 (1)°	Plate, colourless
V = 1739.45 (11) Å3	0.42 × 0.34 × 0.14 mm
Z = 2

Bruker APEXII CCD diffractometer	6503 reflections with I > 2σ(I)
Detector resolution: 0 pixels mm-1	Rint = 0.020
φ and ω scans	θmax = 27.8°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→13
Tmin = 0.756, Tmax = 0.908	k = −17→14
19954 measured reflections	l = −15→15
6614 independent reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.3975P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.021	(Δ/σ)max = 0.001
wR(F2) = 0.055	Δρmax = 0.75 e Å−3
S = 1.06	Δρmin = −0.28 e Å−3
6614 reflections	Absolute structure: Flack (1983), 2322 Friedel pairs
389 parameters	Flack parameter: 0.041 (15)
1 restraint

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C11	0.62500 (19)	0.63257 (16)	0.56623 (17)	0.0192 (4)
C12	0.7541 (2)	0.65504 (18)	0.57934 (19)	0.0238 (4)
H12	0.8061	0.6781	0.649	0.029*
C13	0.8040 (2)	0.6424 (2)	0.4866 (2)	0.0304 (5)
H13	0.8877	0.6614	0.4936	0.036*
C14	0.7305 (2)	0.60220 (18)	0.38554 (19)	0.0247 (5)
H14	0.7665	0.5895	0.3267	0.03*
C15	0.6018 (2)	0.58046 (17)	0.37122 (18)	0.0216 (4)
H15	0.55	0.5578	0.3012	0.026*
C16	0.5517 (2)	0.59328 (18)	0.46349 (19)	0.0230 (4)
H16	0.4675	0.575	0.4557	0.028*
C21	0.5685 (2)	0.51594 (16)	0.74331 (19)	0.0209 (4)
H21	0.5338	0.5188	0.8088	0.025*
C22	0.7053 (2)	0.47939 (19)	0.7908 (2)	0.0297 (5)
H22A	0.7475	0.4834	0.7312	0.036*
H22B	0.7508	0.5221	0.8528	0.036*
C23	0.7135 (3)	0.3754 (2)	0.8343 (2)	0.0347 (6)
H23A	0.6873	0.3738	0.9036	0.042*
H23B	0.8018	0.3537	0.8536	0.042*
C24	0.6306 (3)	0.30502 (19)	0.7477 (3)	0.0379 (6)
H24A	0.6652	0.2982	0.6834	0.046*
H24B	0.6323	0.241	0.7827	0.046*
C25	0.4941 (3)	0.34062 (19)	0.7054 (2)	0.0344 (6)
H25A	0.4557	0.3375	0.7676	0.041*
H25B	0.4461	0.2973	0.6451	0.041*
C26	0.4845 (2)	0.44473 (18)	0.6600 (2)	0.0283 (5)
H26A	0.5085	0.4454	0.5895	0.034*
H26B	0.3963	0.4664	0.6422	0.034*
C31	0.40036 (18)	0.68109 (17)	0.63811 (18)	0.0175 (4)
H31	0.3571	0.6355	0.577	0.021*
C32	0.3332 (2)	0.67641 (18)	0.7323 (2)	0.0236 (4)
H32A	0.3781	0.7179	0.7959	0.028*
H32B	0.3354	0.6096	0.7603	0.028*
C33	0.1933 (2)	0.7106 (2)	0.6862 (2)	0.0346 (6)
H33A	0.1464	0.6653	0.6278	0.042*
H33B	0.1539	0.7104	0.7478	0.042*
C34	0.1855 (3)	0.8127 (2)	0.6359 (2)	0.0354 (6)
H34A	0.2253	0.859	0.6961	0.042*
H34B	0.0964	0.8312	0.6046	0.042*
C35	0.2518 (2)	0.8184 (2)	0.5419 (2)	0.0323 (5)
H35A	0.2495	0.8855	0.5148	0.039*
H35B	0.2067	0.7775	0.478	0.039*
C36	0.3913 (2)	0.78417 (17)	0.5874 (2)	0.0253 (5)
H36A	0.4303	0.7846	0.5255	0.03*
H36B	0.4384	0.8295	0.6457	0.03*
C41	0.61465 (18)	0.98163 (16)	0.93476 (17)	0.0170 (4)
C42	0.4998 (2)	0.93063 (17)	0.91929 (18)	0.0210 (4)
H42	0.4969	0.8635	0.9052	0.025*
C43	0.3901 (2)	0.97931 (19)	0.92474 (19)	0.0257 (5)
H43	0.3146	0.9445	0.9157	0.031*
C44	0.3926 (2)	1.07889 (19)	0.94354 (19)	0.0267 (5)
H44	0.3188	1.1113	0.9466	0.032*
C45	0.5064 (2)	1.13139 (18)	0.95813 (19)	0.0247 (5)
H45	0.5079	1.1989	0.9697	0.03*
C46	0.6173 (2)	1.08229 (17)	0.95532 (18)	0.0199 (4)
H46	0.6935	1.1168	0.9672	0.024*
C51	0.84078 (19)	0.99516 (16)	0.85746 (18)	0.0192 (4)
H51	0.8576	1.0564	0.9014	0.023*
C52	0.7564 (2)	1.0186 (2)	0.7380 (2)	0.0359 (6)
H52A	0.6781	1.0494	0.7428	0.043*
H52B	0.7336	0.9582	0.6948	0.043*
C53	0.8250 (2)	1.0873 (3)	0.6755 (3)	0.0463 (8)
H53A	0.7701	1.1001	0.5988	0.056*
H53B	0.8431	1.1493	0.7159	0.056*
C54	0.9503 (2)	1.0404 (2)	0.6691 (2)	0.0347 (6)
H54A	0.932	0.9798	0.6259	0.042*
H54B	0.9936	1.0844	0.6301	0.042*
C55	1.0355 (2)	1.0198 (2)	0.7882 (2)	0.0283 (5)
H55A	1.0578	1.0812	0.8294	0.034*
H55B	1.114	0.9892	0.7835	0.034*
C56	0.9694 (2)	0.95221 (19)	0.8541 (2)	0.0252 (5)
H56A	0.9555	0.8883	0.8175	0.03*
H56B	1.0244	0.9435	0.9316	0.03*
C61	0.85318 (19)	0.89667 (16)	1.07819 (17)	0.0176 (4)
H61	0.9256	0.8543	1.0778	0.021*
C62	0.9082 (2)	0.98983 (17)	1.1412 (2)	0.0248 (4)
H62A	0.8391	1.0351	1.1394	0.03*
H62B	0.9641	1.0208	1.1025	0.03*
C63	0.9839 (2)	0.9693 (2)	1.2660 (2)	0.0297 (5)
H63A	1.0594	0.9311	1.2679	0.036*
H63B	1.012	1.031	1.3048	0.036*
C64	0.9043 (2)	0.9140 (2)	1.3288 (2)	0.0323 (5)
H64A	0.957	0.8982	1.4055	0.039*
H64B	0.8346	0.9555	1.3355	0.039*
C65	0.8500 (3)	0.8203 (2)	1.2667 (2)	0.0380 (6)
H65A	0.7951	0.7888	1.3061	0.046*
H65B	0.9194	0.7756	1.2677	0.046*
C66	0.7729 (2)	0.8412 (2)	1.1425 (2)	0.0322 (6)
H66A	0.6981	0.8799	1.1416	0.039*
H66B	0.7437	0.7797	1.1036	0.039*
P1	0.56910 (5)	0.64378 (4)	0.69333 (4)	0.01558 (10)
P2	0.75517 (5)	0.91135 (4)	0.92785 (4)	0.01542 (10)
Ag	0.702066 (12)	0.754956 (13)	0.830004 (11)	0.01948 (4)
N	0.9763 (2)	0.69958 (15)	0.93701 (19)	0.0315 (5)
O1	0.94184 (16)	0.71192 (15)	0.83128 (16)	0.0352 (4)
O2	0.8923 (2)	0.67588 (16)	0.98484 (17)	0.0425 (5)
O3	1.08964 (19)	0.71145 (16)	0.9931 (2)	0.0535 (6)

	U11	U22	U33	U12	U13	U23
C11	0.0215 (9)	0.0226 (11)	0.0146 (10)	0.0002 (8)	0.0069 (8)	−0.0013 (8)
C12	0.0194 (9)	0.0303 (12)	0.0206 (11)	−0.0020 (9)	0.0041 (8)	−0.0032 (9)
C13	0.0204 (10)	0.0448 (15)	0.0277 (12)	−0.0036 (10)	0.0099 (9)	−0.0033 (11)
C14	0.0276 (10)	0.0296 (12)	0.0199 (11)	−0.0002 (9)	0.0114 (9)	−0.0007 (9)
C15	0.0229 (10)	0.0249 (11)	0.0154 (10)	−0.0001 (9)	0.0029 (8)	−0.0039 (8)
C16	0.0185 (9)	0.0301 (12)	0.0203 (11)	−0.0037 (9)	0.0055 (8)	−0.0029 (9)
C21	0.0238 (10)	0.0192 (10)	0.0203 (11)	0.0045 (8)	0.0073 (8)	0.0018 (8)
C22	0.0261 (11)	0.0269 (12)	0.0325 (13)	0.0049 (9)	0.0026 (10)	0.0035 (11)
C23	0.0449 (14)	0.0338 (15)	0.0279 (13)	0.0170 (11)	0.0142 (11)	0.0062 (10)
C24	0.0504 (16)	0.0240 (14)	0.0440 (16)	0.0075 (11)	0.0210 (13)	0.0112 (11)
C25	0.0402 (13)	0.0242 (13)	0.0445 (15)	−0.0002 (10)	0.0214 (12)	0.0032 (11)
C26	0.0263 (11)	0.0217 (12)	0.0376 (14)	−0.0022 (9)	0.0103 (10)	0.0026 (10)
C31	0.0136 (8)	0.0222 (11)	0.0150 (10)	0.0021 (7)	0.0015 (7)	−0.0026 (8)
C32	0.0208 (9)	0.0289 (12)	0.0228 (11)	0.0036 (8)	0.0092 (9)	0.0020 (9)
C33	0.0237 (11)	0.0471 (15)	0.0351 (15)	0.0079 (11)	0.0117 (11)	−0.0034 (12)
C34	0.0311 (12)	0.0393 (15)	0.0336 (14)	0.0166 (11)	0.0061 (11)	−0.0034 (12)
C35	0.0372 (13)	0.0303 (13)	0.0253 (12)	0.0159 (11)	0.0027 (10)	0.0018 (10)
C36	0.0288 (11)	0.0240 (12)	0.0222 (11)	0.0065 (8)	0.0058 (9)	0.0036 (8)
C41	0.0172 (9)	0.0208 (10)	0.0125 (9)	0.0037 (8)	0.0037 (7)	0.0031 (8)
C42	0.0217 (10)	0.0235 (11)	0.0168 (10)	−0.0012 (8)	0.0041 (8)	0.0017 (8)
C43	0.0181 (9)	0.0376 (14)	0.0213 (11)	0.0009 (9)	0.0057 (8)	0.0037 (10)
C44	0.0246 (10)	0.0363 (14)	0.0192 (11)	0.0111 (10)	0.0065 (9)	0.0027 (10)
C45	0.0313 (11)	0.0251 (11)	0.0173 (10)	0.0080 (9)	0.0062 (9)	−0.0002 (9)
C46	0.0209 (9)	0.0210 (11)	0.0153 (10)	0.0019 (8)	0.0010 (8)	0.0007 (8)
C51	0.0200 (9)	0.0202 (10)	0.0192 (10)	0.0014 (8)	0.0088 (8)	0.0044 (8)
C52	0.0186 (10)	0.0614 (19)	0.0267 (13)	0.0010 (11)	0.0049 (9)	0.0190 (12)
C53	0.0272 (11)	0.075 (2)	0.0376 (16)	0.0090 (14)	0.0113 (11)	0.0342 (15)
C54	0.0247 (11)	0.0609 (18)	0.0195 (12)	−0.0028 (11)	0.0081 (10)	0.0086 (11)
C55	0.0198 (10)	0.0432 (15)	0.0230 (13)	−0.0013 (10)	0.0081 (9)	0.0018 (11)
C56	0.0202 (10)	0.0330 (13)	0.0224 (11)	0.0049 (9)	0.0061 (9)	0.0063 (9)
C61	0.0161 (9)	0.0187 (10)	0.0158 (10)	−0.0012 (7)	0.0014 (7)	0.0014 (8)
C62	0.0333 (11)	0.0213 (11)	0.0179 (11)	−0.0080 (9)	0.0043 (9)	−0.0013 (9)
C63	0.0291 (11)	0.0372 (14)	0.0196 (12)	−0.0083 (10)	0.0018 (10)	−0.0036 (10)
C64	0.0310 (12)	0.0481 (16)	0.0164 (11)	0.0002 (11)	0.0045 (9)	0.0058 (11)
C65	0.0402 (14)	0.0427 (16)	0.0261 (13)	−0.0098 (12)	0.0018 (11)	0.0140 (12)
C66	0.0345 (12)	0.0365 (15)	0.0207 (12)	−0.0152 (11)	0.0005 (10)	0.0089 (10)
P1	0.0160 (2)	0.0174 (3)	0.0130 (2)	0.00103 (18)	0.00354 (18)	−0.00190 (19)
P2	0.0160 (2)	0.0154 (2)	0.0141 (2)	0.00057 (19)	0.00320 (19)	0.00052 (19)
Ag	0.02057 (7)	0.01953 (7)	0.01629 (7)	−0.00042 (7)	0.00212 (5)	−0.00397 (7)
N	0.0290 (10)	0.0190 (11)	0.0357 (12)	0.0087 (8)	−0.0075 (9)	−0.0074 (8)
O1	0.0291 (8)	0.0424 (11)	0.0296 (10)	0.0055 (7)	0.0012 (7)	−0.0091 (8)
O2	0.0540 (12)	0.0315 (10)	0.0356 (11)	0.0093 (9)	0.0030 (9)	0.0070 (8)
O3	0.0350 (10)	0.0314 (11)	0.0684 (15)	0.0080 (8)	−0.0255 (10)	−0.0150 (10)

C11—C16	1.385 (3)	C42—C43	1.389 (3)
C11—C12	1.406 (3)	C42—H42	0.93
C11—P1	1.832 (2)	C43—C44	1.376 (4)
C12—C13	1.402 (3)	C43—H43	0.93
C12—H12	0.93	C44—C45	1.399 (3)
C13—C14	1.376 (3)	C44—H44	0.93
C13—H13	0.93	C45—C46	1.393 (3)
C14—C15	1.397 (3)	C45—H45	0.93
C14—H14	0.93	C46—H46	0.93
C15—C16	1.399 (3)	C51—C52	1.516 (3)
C15—H15	0.93	C51—C56	1.534 (3)
C16—H16	0.93	C51—P2	1.840 (2)
C21—C26	1.509 (3)	C51—H51	0.98
C21—C22	1.520 (3)	C52—C53	1.534 (4)
C21—P1	1.847 (2)	C52—H52A	0.97
C21—H21	0.98	C52—H52B	0.97
C22—C23	1.508 (4)	C53—C54	1.532 (4)
C22—H22A	0.97	C53—H53A	0.97
C22—H22B	0.97	C53—H53B	0.97
C23—C24	1.516 (4)	C54—C55	1.508 (3)
C23—H23A	0.97	C54—H54A	0.97
C23—H23B	0.97	C54—H54B	0.97
C24—C25	1.509 (4)	C55—C56	1.534 (3)
C24—H24A	0.97	C55—H55A	0.97
C24—H24B	0.97	C55—H55B	0.97
C25—C26	1.516 (3)	C56—H56A	0.97
C25—H25A	0.97	C56—H56B	0.97
C25—H25B	0.97	C61—C62	1.516 (3)
C26—H26A	0.97	C61—C66	1.535 (3)
C26—H26B	0.97	C61—P2	1.848 (2)
C31—C36	1.527 (3)	C61—H61	0.98
C31—C32	1.535 (3)	C62—C63	1.533 (3)
C31—P1	1.840 (2)	C62—H62A	0.97
C31—H31	0.98	C62—H62B	0.97
C32—C33	1.539 (3)	C63—C64	1.517 (3)
C32—H32A	0.97	C63—H63A	0.97
C32—H32B	0.97	C63—H63B	0.97
C33—C34	1.513 (4)	C64—C65	1.517 (4)
C33—H33A	0.97	C64—H64A	0.97
C33—H33B	0.97	C64—H64B	0.97
C34—C35	1.527 (4)	C65—C66	1.533 (3)
C34—H34A	0.97	C65—H65A	0.97
C34—H34B	0.97	C65—H65B	0.97
C35—C36	1.534 (3)	C66—H66A	0.97
C35—H35A	0.97	C66—H66B	0.97
C35—H35B	0.97	P1—Ag	2.4046 (5)
C36—H36A	0.97	P2—Ag	2.4303 (6)
C36—H36B	0.97	N—O3	1.239 (3)
C41—C46	1.394 (3)	N—O1	1.247 (3)
C41—C42	1.398 (3)	N—O2	1.265 (3)
C41—P2	1.832 (2)
C16—C11—C12	118.95 (18)	C42—C43—H43	119.9
C16—C11—P1	123.54 (15)	C43—C44—C45	120.0 (2)
C12—C11—P1	117.10 (16)	C43—C44—H44	120
C13—C12—C11	119.6 (2)	C45—C44—H44	120
C13—C12—H12	120.2	C46—C45—C44	119.8 (2)
C11—C12—H12	120.2	C46—C45—H45	120.1
C14—C13—C12	120.7 (2)	C44—C45—H45	120.1
C14—C13—H13	119.6	C41—C46—C45	120.3 (2)
C12—C13—H13	119.6	C41—C46—H46	119.8
C13—C14—C15	120.02 (19)	C45—C46—H46	119.8
C13—C14—H14	120	C52—C51—C56	111.09 (18)
C15—C14—H14	120	C52—C51—P2	109.34 (15)
C14—C15—C16	119.2 (2)	C56—C51—P2	111.68 (15)
C14—C15—H15	120.4	C52—C51—H51	108.2
C16—C15—H15	120.4	C56—C51—H51	108.2
C11—C16—C15	121.30 (19)	P2—C51—H51	108.2
C11—C16—H16	119.4	C51—C52—C53	111.0 (2)
C15—C16—H16	119.4	C51—C52—H52A	109.4
C26—C21—C22	112.6 (2)	C53—C52—H52A	109.4
C26—C21—P1	116.35 (16)	C51—C52—H52B	109.4
C22—C21—P1	109.75 (16)	C53—C52—H52B	109.4
C26—C21—H21	105.8	H52A—C52—H52B	108
C22—C21—H21	105.8	C54—C53—C52	110.1 (3)
P1—C21—H21	105.8	C54—C53—H53A	109.6
C23—C22—C21	113.2 (2)	C52—C53—H53A	109.6
C23—C22—H22A	108.9	C54—C53—H53B	109.6
C21—C22—H22A	108.9	C52—C53—H53B	109.6
C23—C22—H22B	108.9	H53A—C53—H53B	108.2
C21—C22—H22B	108.9	C55—C54—C53	109.8 (2)
H22A—C22—H22B	107.7	C55—C54—H54A	109.7
C22—C23—C24	112.8 (2)	C53—C54—H54A	109.7
C22—C23—H23A	109	C55—C54—H54B	109.7
C24—C23—H23A	109	C53—C54—H54B	109.7
C22—C23—H23B	109	H54A—C54—H54B	108.2
C24—C23—H23B	109	C54—C55—C56	111.4 (2)
H23A—C23—H23B	107.8	C54—C55—H55A	109.3
C25—C24—C23	111.4 (2)	C56—C55—H55A	109.3
C25—C24—H24A	109.3	C54—C55—H55B	109.3
C23—C24—H24A	109.3	C56—C55—H55B	109.3
C25—C24—H24B	109.3	H55A—C55—H55B	108
C23—C24—H24B	109.3	C51—C56—C55	111.02 (19)
H24A—C24—H24B	108	C51—C56—H56A	109.4
C24—C25—C26	112.5 (2)	C55—C56—H56A	109.4
C24—C25—H25A	109.1	C51—C56—H56B	109.4
C26—C25—H25A	109.1	C55—C56—H56B	109.4
C24—C25—H25B	109.1	H56A—C56—H56B	108
C26—C25—H25B	109.1	C62—C61—C66	110.74 (18)
H25A—C25—H25B	107.8	C62—C61—P2	116.34 (15)
C21—C26—C25	113.1 (2)	C66—C61—P2	108.02 (15)
C21—C26—H26A	109	C62—C61—H61	107.1
C25—C26—H26A	109	C66—C61—H61	107.1
C21—C26—H26B	109	P2—C61—H61	107.1
C25—C26—H26B	109	C61—C62—C63	111.82 (19)
H26A—C26—H26B	107.8	C61—C62—H62A	109.3
C36—C31—C32	110.69 (18)	C63—C62—H62A	109.3
C36—C31—P1	110.06 (15)	C61—C62—H62B	109.3
C32—C31—P1	111.08 (15)	C63—C62—H62B	109.3
C36—C31—H31	108.3	H62A—C62—H62B	107.9
C32—C31—H31	108.3	C64—C63—C62	111.7 (2)
P1—C31—H31	108.3	C64—C63—H63A	109.3
C31—C32—C33	110.64 (19)	C62—C63—H63A	109.3
C31—C32—H32A	109.5	C64—C63—H63B	109.3
C33—C32—H32A	109.5	C62—C63—H63B	109.3
C31—C32—H32B	109.5	H63A—C63—H63B	107.9
C33—C32—H32B	109.5	C65—C64—C63	111.3 (2)
H32A—C32—H32B	108.1	C65—C64—H64A	109.4
C34—C33—C32	111.1 (2)	C63—C64—H64A	109.4
C34—C33—H33A	109.4	C65—C64—H64B	109.4
C32—C33—H33A	109.4	C63—C64—H64B	109.4
C34—C33—H33B	109.4	H64A—C64—H64B	108
C32—C33—H33B	109.4	C64—C65—C66	111.1 (2)
H33A—C33—H33B	108	C64—C65—H65A	109.4
C33—C34—C35	111.6 (2)	C66—C65—H65A	109.4
C33—C34—H34A	109.3	C64—C65—H65B	109.4
C35—C34—H34A	109.3	C66—C65—H65B	109.4
C33—C34—H34B	109.3	H65A—C65—H65B	108
C35—C34—H34B	109.3	C65—C66—C61	111.5 (2)
H34A—C34—H34B	108	C65—C66—H66A	109.3
C34—C35—C36	110.5 (2)	C61—C66—H66A	109.3
C34—C35—H35A	109.6	C65—C66—H66B	109.3
C36—C35—H35A	109.6	C61—C66—H66B	109.3
C34—C35—H35B	109.6	H66A—C66—H66B	108
C36—C35—H35B	109.6	C11—P1—C31	104.92 (10)
H35A—C35—H35B	108.1	C11—P1—C21	103.60 (10)
C31—C36—C35	111.56 (19)	C31—P1—C21	106.42 (10)
C31—C36—H36A	109.3	C11—P1—Ag	110.98 (7)
C35—C36—H36A	109.3	C31—P1—Ag	114.74 (7)
C31—C36—H36B	109.3	C21—P1—Ag	115.12 (7)
C35—C36—H36B	109.3	C41—P2—C51	104.07 (9)
H36A—C36—H36B	108	C41—P2—C61	105.19 (9)
C46—C41—C42	119.01 (19)	C51—P2—C61	107.77 (10)
C46—C41—P2	123.32 (16)	C41—P2—Ag	113.46 (7)
C42—C41—P2	117.66 (16)	C51—P2—Ag	113.33 (7)
C43—C42—C41	120.6 (2)	C61—P2—Ag	112.34 (7)
C43—C42—H42	119.7	P1—Ag—P2	154.662 (19)
C41—C42—H42	119.7	O3—N—O1	120.5 (2)
C44—C43—C42	120.2 (2)	O3—N—O2	121.4 (2)
C44—C43—H43	119.9	O1—N—O2	118.1 (2)
C16—C11—C12—C13	3.5 (4)	C64—C65—C66—C61	55.6 (3)
P1—C11—C12—C13	176.4 (2)	C62—C61—C66—C65	−55.0 (3)
C11—C12—C13—C14	−4.3 (4)	P2—C61—C66—C65	176.6 (2)
C12—C13—C14—C15	4.9 (4)	C16—C11—P1—C31	−39.6 (2)
C13—C14—C15—C16	−4.7 (4)	C12—C11—P1—C31	147.89 (18)
C12—C11—C16—C15	−3.4 (4)	C16—C11—P1—C21	71.9 (2)
P1—C11—C16—C15	−175.79 (19)	C12—C11—P1—C21	−100.68 (19)
C14—C15—C16—C11	4.0 (4)	C16—C11—P1—Ag	−164.03 (18)
C26—C21—C22—C23	−49.1 (3)	C12—C11—P1—Ag	23.4 (2)
P1—C21—C22—C23	179.65 (17)	C36—C31—P1—C11	−66.86 (17)
C21—C22—C23—C24	51.1 (3)	C32—C31—P1—C11	170.20 (16)
C22—C23—C24—C25	−53.0 (3)	C36—C31—P1—C21	−176.26 (15)
C23—C24—C25—C26	53.3 (3)	C32—C31—P1—C21	60.80 (18)
C22—C21—C26—C25	49.5 (3)	C36—C31—P1—Ag	55.19 (15)
P1—C21—C26—C25	177.35 (16)	C32—C31—P1—Ag	−67.75 (17)
C24—C25—C26—C21	−52.2 (3)	C26—C21—P1—C11	−59.47 (17)
C36—C31—C32—C33	55.8 (3)	C22—C21—P1—C11	69.78 (18)
P1—C31—C32—C33	178.34 (18)	C26—C21—P1—C31	50.86 (18)
C31—C32—C33—C34	−56.2 (3)	C22—C21—P1—C31	−179.89 (16)
C32—C33—C34—C35	56.5 (3)	C26—C21—P1—Ag	179.19 (13)
C33—C34—C35—C36	−55.8 (3)	C22—C21—P1—Ag	−51.57 (17)
C32—C31—C36—C35	−56.0 (2)	C46—C41—P2—C51	−37.0 (2)
P1—C31—C36—C35	−179.19 (16)	C42—C41—P2—C51	143.49 (17)
C34—C35—C36—C31	55.6 (3)	C46—C41—P2—C61	76.23 (19)
C46—C41—C42—C43	−0.3 (3)	C42—C41—P2—C61	−103.30 (17)
P2—C41—C42—C43	179.29 (17)	C46—C41—P2—Ag	−160.60 (15)
C41—C42—C43—C44	1.1 (3)	C42—C41—P2—Ag	19.87 (18)
C42—C43—C44—C45	−0.5 (3)	C52—C51—P2—C41	−62.04 (19)
C43—C44—C45—C46	−1.0 (3)	C56—C51—P2—C41	174.61 (16)
C42—C41—C46—C45	−1.2 (3)	C52—C51—P2—C61	−173.38 (17)
P2—C41—C46—C45	179.25 (16)	C56—C51—P2—C61	63.27 (18)
C44—C45—C46—C41	1.9 (3)	C52—C51—P2—Ag	61.67 (18)
C56—C51—C52—C53	−55.5 (3)	C56—C51—P2—Ag	−61.68 (17)
P2—C51—C52—C53	−179.2 (2)	C62—C61—P2—C41	−65.12 (17)
C51—C52—C53—C54	58.0 (3)	C66—C61—P2—C41	60.08 (18)
C52—C53—C54—C55	−58.9 (3)	C62—C61—P2—C51	45.45 (18)
C53—C54—C55—C56	58.1 (3)	C66—C61—P2—C51	170.66 (16)
C52—C51—C56—C55	53.9 (3)	C62—C61—P2—Ag	171.00 (13)
P2—C51—C56—C55	176.25 (16)	C66—C61—P2—Ag	−63.80 (17)
C54—C55—C56—C51	−55.7 (3)	C11—P1—Ag—P2	100.90 (8)
C66—C61—C62—C63	54.3 (3)	C31—P1—Ag—P2	−17.80 (9)
P2—C61—C62—C63	178.13 (16)	C21—P1—Ag—P2	−141.85 (8)
C61—C62—C63—C64	−54.7 (3)	C41—P2—Ag—P1	29.07 (9)
C62—C63—C64—C65	54.9 (3)	C51—P2—Ag—P1	−89.33 (8)
C63—C64—C65—C66	−55.4 (3)	C61—P2—Ag—P1	148.22 (7)