(N-Phenyl-thio-urea-κS)bis-(tri-phenylphosphane-κP)silver(I) nitrate.

In the title salt, [Ag(C7H8N2S)(C18H15P)2]NO3, the coordination geometry about the Ag(I) atom is shallow trigonal pyramidal, with the metal atom displaced by 0.372 (1) Å from the plane of the P and S atoms. In the crystal, the cations are linked to the anions by N-H⋯O hydrogen bonds, generating tetra-mers (two cations and two anions), which feature R 2 (2)(8) and R 4 (4)(8) loops. The cations are linked by weak C-H⋯π inter-actions, generating a three-dimensional network.

Related literature

For properties of mixed-ligand d 10 metal(I) complexes, see: Oshio et al. (1996 ▶); Zheng et al. (2001 ▶); Sewead et al. (2003 ▶); Isab et al. (2010 ▶). For structural studies of mixed-ligand complexes of tri­phenyl­phosphane and thione ligands, see: Skoulika et al. (1991 ▶); Aslanidis et al. (1997 ▶); Ghassemzadeh et al.(2004 ▶); Nimthong et al. (2008 ▶); Isab et al. (2010 ▶).

Experimental

Crystal data

[Ag(C7H8N2S)(C18H15P)2]NO3

M = 846.63

Monoclinic,

a = 13.6113 (5) Å

b = 10.6431 (4) Å

c = 26.4365 (10) Å

β = 96.068 (1)°

V = 3808.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.71 mm−1

T = 173 K

0.27 × 0.14 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.863, T max = 1.000

44417 measured reflections

9196 independent reflections

8261 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.064

S = 1.05

9196 reflections

478 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010) ▶.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814014147/hb7242sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014147/hb7242Isup2.hkl

CCDC reference: 1008627

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

[Ag(C7H8N2S)(C18H15P)2]NO3	F(000) = 1736
Mr = 846.63	Dx = 1.477 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6113 (5) Å	Cell parameters from 13930 reflections
b = 10.6431 (4) Å	θ = 2.3–28.0°
c = 26.4365 (10) Å	µ = 0.71 mm−1
β = 96.068 (1)°	T = 173 K
V = 3808.3 (2) Å3	Block, colourless
Z = 4	0.27 × 0.14 × 0.08 mm

Bruker SMART CCD diffractometer	8261 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Frames each covering 0.3 ° in ω scans	θmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −17→17
Tmin = 0.863, Tmax = 1.000	k = −14→14
44417 measured reflections	l = −34→34
9196 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0264P)2 + 2.6456P] where P = (Fo2 + 2Fc2)/3
9196 reflections	(Δ/σ)max = 0.003
478 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.26 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.

	x	y	z	Uiso*/Ueq
Ag1	0.30947 (2)	0.80538 (2)	0.87530 (2)	0.01346 (4)
S1	0.27373 (3)	0.65461 (4)	0.94508 (2)	0.01679 (9)
P1	0.48557 (3)	0.81150 (4)	0.86130 (2)	0.01253 (8)
P2	0.18820 (3)	0.97824 (4)	0.86365 (2)	0.01356 (9)
N1	0.10876 (11)	0.54151 (15)	0.96207 (6)	0.0205 (3)
H1A	0.0553	0.5001	0.9535	0.025*
H1B	0.1249	0.5609	0.9934	0.025*
N2	0.13553 (11)	0.54123 (15)	0.87904 (6)	0.0195 (3)
H2	0.0848	0.4926	0.8754	0.023*
N3	0.91546 (11)	0.35396 (14)	0.88996 (6)	0.0200 (3)
O1	0.98030 (10)	0.36618 (14)	0.85981 (5)	0.0285 (3)
O2	0.83834 (11)	0.29694 (14)	0.87678 (6)	0.0339 (4)
O3	0.92984 (10)	0.40319 (15)	0.93362 (5)	0.0320 (3)
C1	0.16649 (13)	0.57551 (16)	0.92682 (6)	0.0166 (3)
C2	0.17639 (13)	0.57559 (16)	0.83349 (6)	0.0165 (3)
C3	0.27222 (13)	0.54423 (18)	0.82506 (7)	0.0203 (4)
H3	0.3129	0.5015	0.8498	0.024*
C4	0.30689 (14)	0.57740 (19)	0.77919 (7)	0.0246 (4)
H4	0.3714	0.5580	0.7735	0.030*
C5	0.24611 (15)	0.63894 (18)	0.74210 (7)	0.0244 (4)
H5	0.2700	0.6612	0.7117	0.029*
C6	0.14981 (15)	0.66765 (17)	0.75003 (7)	0.0233 (4)
H6	0.1086	0.7080	0.7248	0.028*
C7	0.11484 (14)	0.63599 (18)	0.79586 (7)	0.0212 (4)
H7	0.0502	0.6553	0.8013	0.025*
C11	0.56534 (12)	0.68448 (15)	0.88711 (6)	0.0142 (3)
C12	0.66839 (13)	0.69391 (16)	0.88805 (6)	0.0160 (3)
H12	0.6962	0.7659	0.8756	0.019*
C13	0.72891 (13)	0.59703 (17)	0.90730 (6)	0.0168 (3)
H13	0.7970	0.6032	0.9070	0.020*
C14	0.68800 (13)	0.49043 (16)	0.92701 (6)	0.0178 (3)
H14	0.7285	0.4246	0.9394	0.021*
C15	0.58661 (13)	0.48238 (16)	0.92812 (6)	0.0178 (3)
H15	0.5596	0.4123	0.9425	0.021*
C16	0.52496 (13)	0.57825 (16)	0.90794 (6)	0.0154 (3)
H16	0.4569	0.5716	0.9083	0.018*
C21	0.55372 (12)	0.94570 (15)	0.89023 (6)	0.0136 (3)
C22	0.59006 (12)	1.04369 (16)	0.86294 (6)	0.0161 (3)
H22	0.5778	1.0452	0.8277	0.019*
C23	0.64480 (13)	1.13972 (17)	0.88827 (7)	0.0182 (3)
H23	0.6684	1.2056	0.8698	0.022*
C24	0.66425 (13)	1.13752 (17)	0.94081 (7)	0.0195 (4)
H24	0.7028	1.2001	0.9575	0.023*
C25	0.62590 (14)	1.04144 (17)	0.96837 (7)	0.0211 (4)
H25	0.6374	1.0408	1.0037	0.025*
C26	0.57049 (13)	0.94653 (17)	0.94329 (6)	0.0187 (4)
H26	0.5443	0.8829	0.9619	0.022*
C31	0.50225 (12)	0.81928 (15)	0.79374 (6)	0.0135 (3)
C32	0.57450 (13)	0.75263 (17)	0.77151 (7)	0.0183 (3)
H32	0.6192	0.7031	0.7917	0.022*
C33	0.58030 (14)	0.75957 (18)	0.71953 (7)	0.0213 (4)
H33	0.6288	0.7147	0.7050	0.026*
C34	0.51386 (14)	0.83325 (17)	0.68905 (7)	0.0211 (4)
H34	0.5178	0.8377	0.6542	0.025*
C35	0.44182 (14)	0.90008 (17)	0.71074 (7)	0.0208 (4)
H35	0.3974	0.9498	0.6904	0.025*
C36	0.43562 (13)	0.89312 (17)	0.76278 (7)	0.0181 (3)
H36	0.3868	0.9379	0.7771	0.022*
C41	0.06641 (13)	0.94975 (16)	0.88407 (7)	0.0166 (3)
C42	−0.01987 (14)	0.99999 (19)	0.85980 (8)	0.0263 (4)
H42	−0.0179	1.0465	0.8301	0.032*
C43	−0.10945 (14)	0.9812 (2)	0.87964 (9)	0.0314 (5)
H43	−0.1670	1.0157	0.8633	0.038*
C44	−0.11355 (14)	0.91173 (19)	0.92340 (8)	0.0270 (4)
H44	−0.1735	0.8999	0.9367	0.032*
C45	−0.02773 (15)	0.8597 (2)	0.94747 (8)	0.0288 (4)
H45	−0.0301	0.8124	0.9769	0.035*
C46	0.06196 (14)	0.87786 (19)	0.92784 (7)	0.0242 (4)
H46	0.1192	0.8419	0.9440	0.029*
C51	0.23925 (12)	1.10092 (15)	0.90686 (6)	0.0149 (3)
C52	0.33905 (13)	1.12973 (16)	0.90577 (7)	0.0178 (3)
H52	0.3765	1.0845	0.8846	0.021*
C53	0.38268 (14)	1.22486 (17)	0.93583 (7)	0.0216 (4)
H53	0.4492	1.2435	0.9347	0.026*
C54	0.32787 (15)	1.29242 (17)	0.96757 (7)	0.0237 (4)
H54	0.3572	1.3568	0.9876	0.028*
C55	0.22880 (15)	1.26367 (18)	0.96936 (7)	0.0237 (4)
H55	0.1920	1.3084	0.9910	0.028*
C56	0.18420 (14)	1.16877 (17)	0.93912 (7)	0.0206 (4)
H56	0.1177	1.1504	0.9404	0.025*
C61	0.16834 (12)	1.06410 (16)	0.80372 (6)	0.0153 (3)
C62	0.14519 (14)	1.19195 (17)	0.80202 (7)	0.0200 (4)
H62	0.1353	1.2345	0.8318	0.024*
C63	0.13683 (14)	1.25589 (18)	0.75580 (7)	0.0233 (4)
H63	0.1217	1.3411	0.7548	0.028*
C64	0.15107 (14)	1.19286 (19)	0.71128 (7)	0.0230 (4)
H64	0.1459	1.2358	0.6805	0.028*
C65	0.17304 (14)	1.06573 (19)	0.71274 (7)	0.0237 (4)
H65	0.1819	1.0231	0.6828	0.028*
C66	0.18175 (13)	1.00199 (18)	0.75869 (7)	0.0192 (4)
H66	0.1967	0.9167	0.7594	0.023*

	U11	U22	U33	U12	U13	U23
Ag1	0.01252 (7)	0.01365 (6)	0.01457 (6)	−0.00079 (4)	0.00304 (4)	0.00008 (5)
S1	0.0166 (2)	0.0204 (2)	0.01331 (19)	−0.00489 (16)	0.00144 (15)	0.00208 (16)
P1	0.01206 (19)	0.01232 (19)	0.01342 (19)	−0.00013 (15)	0.00226 (15)	0.00091 (15)
P2	0.0125 (2)	0.0139 (2)	0.0147 (2)	0.00012 (15)	0.00337 (16)	0.00002 (16)
N1	0.0186 (7)	0.0264 (8)	0.0170 (7)	−0.0071 (6)	0.0043 (6)	0.0003 (6)
N2	0.0160 (7)	0.0250 (8)	0.0178 (7)	−0.0085 (6)	0.0036 (6)	−0.0010 (6)
N3	0.0158 (7)	0.0192 (7)	0.0258 (8)	−0.0008 (6)	0.0057 (6)	−0.0009 (6)
O1	0.0226 (7)	0.0375 (8)	0.0274 (7)	−0.0110 (6)	0.0122 (6)	−0.0076 (6)
O2	0.0222 (7)	0.0362 (8)	0.0449 (9)	−0.0150 (6)	0.0110 (6)	−0.0154 (7)
O3	0.0241 (7)	0.0499 (9)	0.0235 (7)	−0.0120 (7)	0.0093 (6)	−0.0110 (7)
C1	0.0168 (8)	0.0157 (8)	0.0175 (8)	−0.0003 (6)	0.0033 (6)	0.0020 (6)
C2	0.0171 (8)	0.0184 (8)	0.0142 (8)	−0.0059 (7)	0.0033 (6)	−0.0021 (6)
C3	0.0192 (9)	0.0233 (9)	0.0179 (8)	−0.0016 (7)	0.0004 (7)	−0.0015 (7)
C4	0.0212 (9)	0.0318 (10)	0.0221 (9)	−0.0022 (8)	0.0086 (7)	−0.0056 (8)
C5	0.0331 (11)	0.0249 (10)	0.0161 (9)	−0.0078 (8)	0.0076 (8)	−0.0037 (7)
C6	0.0300 (10)	0.0204 (9)	0.0183 (9)	−0.0027 (8)	−0.0032 (7)	−0.0008 (7)
C7	0.0168 (9)	0.0253 (9)	0.0214 (9)	−0.0018 (7)	0.0007 (7)	−0.0029 (7)
C11	0.0164 (8)	0.0131 (7)	0.0129 (7)	0.0005 (6)	0.0013 (6)	−0.0007 (6)
C12	0.0174 (8)	0.0162 (8)	0.0150 (8)	−0.0011 (6)	0.0037 (6)	0.0011 (6)
C13	0.0144 (8)	0.0223 (9)	0.0134 (8)	0.0021 (7)	0.0010 (6)	−0.0021 (7)
C14	0.0231 (9)	0.0159 (8)	0.0136 (8)	0.0049 (7)	−0.0012 (7)	−0.0013 (6)
C15	0.0244 (9)	0.0123 (8)	0.0164 (8)	−0.0021 (7)	0.0010 (7)	0.0011 (6)
C16	0.0159 (8)	0.0159 (8)	0.0144 (8)	−0.0018 (6)	0.0020 (6)	−0.0010 (6)
C21	0.0114 (7)	0.0135 (8)	0.0161 (8)	0.0015 (6)	0.0022 (6)	−0.0014 (6)
C22	0.0169 (8)	0.0187 (8)	0.0128 (8)	−0.0017 (7)	0.0027 (6)	−0.0001 (6)
C23	0.0183 (8)	0.0175 (8)	0.0194 (8)	−0.0029 (7)	0.0051 (7)	0.0014 (7)
C24	0.0186 (9)	0.0173 (8)	0.0220 (9)	−0.0014 (7)	−0.0009 (7)	−0.0050 (7)
C25	0.0288 (10)	0.0213 (9)	0.0127 (8)	0.0016 (7)	−0.0007 (7)	−0.0005 (7)
C26	0.0244 (9)	0.0168 (8)	0.0155 (8)	0.0005 (7)	0.0043 (7)	0.0027 (7)
C31	0.0139 (8)	0.0137 (8)	0.0127 (7)	−0.0033 (6)	0.0012 (6)	−0.0001 (6)
C32	0.0187 (9)	0.0188 (8)	0.0172 (8)	0.0037 (7)	0.0010 (7)	0.0002 (7)
C33	0.0233 (9)	0.0237 (9)	0.0177 (8)	0.0033 (7)	0.0064 (7)	−0.0028 (7)
C34	0.0273 (10)	0.0220 (9)	0.0139 (8)	−0.0034 (7)	0.0022 (7)	−0.0007 (7)
C35	0.0234 (9)	0.0203 (9)	0.0177 (8)	0.0018 (7)	−0.0023 (7)	0.0026 (7)
C36	0.0163 (8)	0.0194 (8)	0.0187 (8)	0.0023 (7)	0.0024 (7)	0.0001 (7)
C41	0.0157 (8)	0.0154 (8)	0.0195 (8)	−0.0010 (6)	0.0052 (7)	−0.0014 (7)
C42	0.0187 (9)	0.0299 (10)	0.0304 (10)	0.0013 (8)	0.0036 (8)	0.0087 (8)
C43	0.0140 (9)	0.0384 (12)	0.0419 (12)	0.0027 (8)	0.0038 (8)	0.0075 (10)
C44	0.0184 (9)	0.0279 (10)	0.0370 (11)	−0.0036 (8)	0.0127 (8)	−0.0025 (9)
C45	0.0280 (10)	0.0315 (11)	0.0292 (10)	0.0013 (8)	0.0134 (8)	0.0067 (9)
C46	0.0187 (9)	0.0277 (10)	0.0273 (10)	0.0044 (7)	0.0074 (7)	0.0059 (8)
C51	0.0166 (8)	0.0140 (8)	0.0140 (8)	0.0008 (6)	0.0014 (6)	0.0021 (6)
C52	0.0204 (9)	0.0167 (8)	0.0169 (8)	0.0002 (7)	0.0042 (7)	0.0001 (7)
C53	0.0221 (9)	0.0205 (9)	0.0219 (9)	−0.0063 (7)	0.0012 (7)	0.0018 (7)
C54	0.0344 (11)	0.0175 (9)	0.0181 (9)	−0.0032 (8)	−0.0020 (8)	−0.0022 (7)
C55	0.0294 (10)	0.0224 (9)	0.0199 (9)	0.0038 (8)	0.0055 (8)	−0.0043 (7)
C56	0.0202 (9)	0.0229 (9)	0.0192 (9)	0.0020 (7)	0.0042 (7)	−0.0015 (7)
C61	0.0117 (8)	0.0179 (8)	0.0165 (8)	−0.0014 (6)	0.0027 (6)	0.0017 (6)
C62	0.0212 (9)	0.0206 (9)	0.0184 (8)	0.0013 (7)	0.0033 (7)	0.0000 (7)
C63	0.0243 (10)	0.0200 (9)	0.0253 (9)	−0.0001 (7)	0.0007 (8)	0.0057 (8)
C64	0.0176 (9)	0.0336 (10)	0.0180 (9)	−0.0039 (8)	0.0021 (7)	0.0077 (8)
C65	0.0208 (9)	0.0346 (11)	0.0162 (8)	−0.0033 (8)	0.0041 (7)	−0.0027 (8)
C66	0.0174 (8)	0.0211 (9)	0.0194 (8)	−0.0014 (7)	0.0028 (7)	−0.0024 (7)

Ag1—P1	2.4645 (5)	C24—H24	0.9300
Ag1—P2	2.4693 (4)	C25—C26	1.387 (3)
Ag1—S1	2.5307 (4)	C25—H25	0.9300
S1—C1	1.7098 (18)	C26—H26	0.9300
P1—C11	1.8208 (17)	C31—C32	1.392 (2)
P1—C31	1.8260 (17)	C31—C36	1.398 (2)
P1—C21	1.8262 (17)	C32—C33	1.387 (2)
P2—C41	1.8222 (18)	C32—H32	0.9300
P2—C51	1.8235 (17)	C33—C34	1.389 (3)
P2—C61	1.8241 (17)	C33—H33	0.9300
N1—C1	1.331 (2)	C34—C35	1.384 (3)
N1—H1A	0.8600	C34—H34	0.9300
N1—H1B	0.8600	C35—C36	1.389 (2)
N2—C1	1.339 (2)	C35—H35	0.9300
N2—C2	1.426 (2)	C36—H36	0.9300
N2—H2	0.8600	C41—C42	1.385 (3)
N3—O2	1.231 (2)	C41—C46	1.394 (3)
N3—O1	1.2568 (19)	C42—C43	1.392 (3)
N3—O3	1.264 (2)	C42—H42	0.9300
C2—C3	1.387 (2)	C43—C44	1.379 (3)
C2—C7	1.389 (2)	C43—H43	0.9300
C3—C4	1.392 (3)	C44—C45	1.385 (3)
C3—H3	0.9300	C44—H44	0.9300
C4—C5	1.380 (3)	C45—C46	1.390 (3)
C4—H4	0.9300	C45—H45	0.9300
C5—C6	1.383 (3)	C46—H46	0.9300
C5—H5	0.9300	C51—C56	1.395 (2)
C6—C7	1.389 (3)	C51—C52	1.396 (2)
C6—H6	0.9300	C52—C53	1.382 (2)
C7—H7	0.9300	C52—H52	0.9300
C11—C16	1.396 (2)	C53—C54	1.382 (3)
C11—C12	1.404 (2)	C53—H53	0.9300
C12—C13	1.383 (2)	C54—C55	1.388 (3)
C12—H12	0.9300	C54—H54	0.9300
C13—C14	1.389 (2)	C55—C56	1.387 (3)
C13—H13	0.9300	C55—H55	0.9300
C14—C15	1.386 (3)	C56—H56	0.9300
C14—H14	0.9300	C61—C66	1.391 (2)
C15—C16	1.391 (2)	C61—C62	1.396 (2)
C15—H15	0.9300	C62—C63	1.393 (3)
C16—H16	0.9300	C62—H62	0.9300
C21—C22	1.389 (2)	C63—C64	1.386 (3)
C21—C26	1.397 (2)	C63—H63	0.9300
C22—C23	1.394 (2)	C64—C65	1.385 (3)
C22—H22	0.9300	C64—H64	0.9300
C23—C24	1.387 (2)	C65—C66	1.386 (3)
C23—H23	0.9300	C65—H65	0.9300
C24—C25	1.389 (3)	C66—H66	0.9300
P1—Ag1—P2	127.556 (15)	C26—C25—H25	120.0
P1—Ag1—S1	113.029 (15)	C24—C25—H25	120.0
P2—Ag1—S1	112.694 (15)	C25—C26—C21	120.50 (16)
C1—S1—Ag1	109.30 (6)	C25—C26—H26	119.7
C11—P1—C31	105.62 (8)	C21—C26—H26	119.7
C11—P1—C21	99.64 (8)	C32—C31—C36	118.88 (15)
C31—P1—C21	105.30 (8)	C32—C31—P1	123.80 (13)
C11—P1—Ag1	118.36 (6)	C36—C31—P1	117.27 (13)
C31—P1—Ag1	111.81 (6)	C33—C32—C31	120.52 (16)
C21—P1—Ag1	114.63 (5)	C33—C32—H32	119.7
C41—P2—C51	103.41 (8)	C31—C32—H32	119.7
C41—P2—C61	106.55 (8)	C32—C33—C34	120.23 (17)
C51—P2—C61	101.36 (8)	C32—C33—H33	119.9
C41—P2—Ag1	117.14 (6)	C34—C33—H33	119.9
C51—P2—Ag1	104.48 (6)	C35—C34—C33	119.75 (17)
C61—P2—Ag1	121.15 (6)	C35—C34—H34	120.1
C1—N1—H1A	120.0	C33—C34—H34	120.1
C1—N1—H1B	120.0	C34—C35—C36	120.19 (17)
H1A—N1—H1B	120.0	C34—C35—H35	119.9
C1—N2—C2	127.91 (15)	C36—C35—H35	119.9
C1—N2—H2	116.0	C35—C36—C31	120.42 (16)
C2—N2—H2	116.0	C35—C36—H36	119.8
O2—N3—O1	120.45 (16)	C31—C36—H36	119.8
O2—N3—O3	120.53 (15)	C42—C41—C46	119.18 (17)
O1—N3—O3	119.01 (15)	C42—C41—P2	123.50 (14)
N1—C1—N2	115.86 (16)	C46—C41—P2	117.26 (13)
N1—C1—S1	119.06 (13)	C41—C42—C43	120.24 (18)
N2—C1—S1	125.06 (13)	C41—C42—H42	119.9
C3—C2—C7	120.16 (16)	C43—C42—H42	119.9
C3—C2—N2	122.09 (16)	C44—C43—C42	120.54 (19)
C7—C2—N2	117.64 (16)	C44—C43—H43	119.7
C2—C3—C4	119.35 (17)	C42—C43—H43	119.7
C2—C3—H3	120.3	C43—C44—C45	119.52 (18)
C4—C3—H3	120.3	C43—C44—H44	120.2
C5—C4—C3	120.43 (18)	C45—C44—H44	120.2
C5—C4—H4	119.8	C44—C45—C46	120.28 (19)
C3—C4—H4	119.8	C44—C45—H45	119.9
C4—C5—C6	120.25 (18)	C46—C45—H45	119.9
C4—C5—H5	119.9	C45—C46—C41	120.23 (18)
C6—C5—H5	119.9	C45—C46—H46	119.9
C5—C6—C7	119.74 (18)	C41—C46—H46	119.9
C5—C6—H6	120.1	C56—C51—C52	119.07 (16)
C7—C6—H6	120.1	C56—C51—P2	124.06 (13)
C2—C7—C6	120.05 (17)	C52—C51—P2	116.84 (13)
C2—C7—H7	120.0	C53—C52—C51	120.60 (17)
C6—C7—H7	120.0	C53—C52—H52	119.7
C16—C11—C12	119.03 (15)	C51—C52—H52	119.7
C16—C11—P1	120.35 (13)	C52—C53—C54	120.24 (18)
C12—C11—P1	120.58 (13)	C52—C53—H53	119.9
C13—C12—C11	120.56 (16)	C54—C53—H53	119.9
C13—C12—H12	119.7	C53—C54—C55	119.64 (17)
C11—C12—H12	119.7	C53—C54—H54	120.2
C12—C13—C14	120.01 (16)	C55—C54—H54	120.2
C12—C13—H13	120.0	C56—C55—C54	120.54 (18)
C14—C13—H13	120.0	C56—C55—H55	119.7
C15—C14—C13	119.86 (16)	C54—C55—H55	119.7
C15—C14—H14	120.1	C55—C56—C51	119.91 (17)
C13—C14—H14	120.1	C55—C56—H56	120.0
C14—C15—C16	120.54 (16)	C51—C56—H56	120.0
C14—C15—H15	119.7	C66—C61—C62	119.03 (16)
C16—C15—H15	119.7	C66—C61—P2	118.99 (13)
C15—C16—C11	119.92 (16)	C62—C61—P2	121.89 (13)
C15—C16—H16	120.0	C63—C62—C61	120.10 (17)
C11—C16—H16	120.0	C63—C62—H62	119.9
C22—C21—C26	119.17 (15)	C61—C62—H62	119.9
C22—C21—P1	124.26 (13)	C64—C63—C62	120.18 (18)
C26—C21—P1	116.56 (13)	C64—C63—H63	119.9
C21—C22—C23	120.20 (16)	C62—C63—H63	119.9
C21—C22—H22	119.9	C65—C64—C63	119.90 (17)
C23—C22—H22	119.9	C65—C64—H64	120.1
C24—C23—C22	120.30 (16)	C63—C64—H64	120.1
C24—C23—H23	119.9	C64—C65—C66	120.05 (18)
C22—C23—H23	119.8	C64—C65—H65	120.0
C23—C24—C25	119.70 (16)	C66—C65—H65	120.0
C23—C24—H24	120.2	C65—C66—C61	120.74 (17)
C25—C24—H24	120.2	C65—C66—H66	119.6
C26—C25—C24	120.06 (16)	C61—C66—H66	119.6
C2—N2—C1—N1	172.88 (17)	P1—C31—C32—C33	177.53 (14)
C2—N2—C1—S1	−8.7 (3)	C31—C32—C33—C34	0.0 (3)
Ag1—S1—C1—N1	−147.45 (13)	C32—C33—C34—C35	0.1 (3)
Ag1—S1—C1—N2	34.16 (17)	C33—C34—C35—C36	−0.3 (3)
C1—N2—C2—C3	61.7 (3)	C34—C35—C36—C31	0.4 (3)
C1—N2—C2—C7	−122.0 (2)	C32—C31—C36—C35	−0.3 (3)
C7—C2—C3—C4	2.0 (3)	P1—C31—C36—C35	−177.86 (14)
N2—C2—C3—C4	178.19 (17)	C51—P2—C41—C42	99.52 (17)
C2—C3—C4—C5	−1.1 (3)	C61—P2—C41—C42	−6.87 (18)
C3—C4—C5—C6	−0.4 (3)	Ag1—P2—C41—C42	−146.22 (15)
C4—C5—C6—C7	1.0 (3)	C51—P2—C41—C46	−77.57 (15)
C3—C2—C7—C6	−1.4 (3)	C61—P2—C41—C46	176.04 (14)
N2—C2—C7—C6	−177.76 (16)	Ag1—P2—C41—C46	36.69 (16)
C5—C6—C7—C2	−0.1 (3)	C46—C41—C42—C43	1.5 (3)
C31—P1—C11—C16	−117.34 (14)	P2—C41—C42—C43	−175.56 (16)
C21—P1—C11—C16	133.67 (14)	C41—C42—C43—C44	−0.4 (3)
Ag1—P1—C11—C16	8.77 (16)	C42—C43—C44—C45	−0.5 (3)
C31—P1—C11—C12	65.03 (15)	C43—C44—C45—C46	0.3 (3)
C21—P1—C11—C12	−43.97 (15)	C44—C45—C46—C41	0.7 (3)
Ag1—P1—C11—C12	−168.87 (11)	C42—C41—C46—C45	−1.6 (3)
C16—C11—C12—C13	2.8 (2)	P2—C41—C46—C45	175.61 (16)
P1—C11—C12—C13	−179.50 (13)	C41—P2—C51—C56	−11.67 (17)
C11—C12—C13—C14	−1.5 (3)	C61—P2—C51—C56	98.60 (16)
C12—C13—C14—C15	−1.1 (3)	Ag1—P2—C51—C56	−134.76 (14)
C13—C14—C15—C16	2.4 (3)	C41—P2—C51—C52	170.39 (13)
C14—C15—C16—C11	−1.0 (3)	C61—P2—C51—C52	−79.34 (14)
C12—C11—C16—C15	−1.6 (2)	Ag1—P2—C51—C52	47.30 (14)
P1—C11—C16—C15	−179.23 (13)	C56—C51—C52—C53	−0.6 (3)
C11—P1—C21—C22	121.60 (15)	P2—C51—C52—C53	177.44 (14)
C31—P1—C21—C22	12.36 (16)	C51—C52—C53—C54	0.3 (3)
Ag1—P1—C21—C22	−110.96 (14)	C52—C53—C54—C55	0.4 (3)
C11—P1—C21—C26	−57.49 (14)	C53—C54—C55—C56	−0.8 (3)
C31—P1—C21—C26	−166.73 (13)	C54—C55—C56—C51	0.4 (3)
Ag1—P1—C21—C26	69.95 (14)	C52—C51—C56—C55	0.2 (3)
C26—C21—C22—C23	1.7 (3)	P2—C51—C56—C55	−177.65 (14)
P1—C21—C22—C23	−177.36 (13)	C41—P2—C61—C66	−106.80 (14)
C21—C22—C23—C24	0.7 (3)	C51—P2—C61—C66	145.35 (14)
C22—C23—C24—C25	−2.3 (3)	Ag1—P2—C61—C66	30.55 (16)
C23—C24—C25—C26	1.6 (3)	C41—P2—C61—C62	76.64 (16)
C24—C25—C26—C21	0.8 (3)	C51—P2—C61—C62	−31.20 (16)
C22—C21—C26—C25	−2.4 (3)	Ag1—P2—C61—C62	−146.00 (13)
P1—C21—C26—C25	176.72 (14)	C66—C61—C62—C63	−0.7 (3)
C11—P1—C31—C32	−9.27 (17)	P2—C61—C62—C63	175.88 (14)
C21—P1—C31—C32	95.60 (15)	C61—C62—C63—C64	0.2 (3)
Ag1—P1—C31—C32	−139.30 (13)	C62—C63—C64—C65	0.4 (3)
C11—P1—C31—C36	168.20 (13)	C63—C64—C65—C66	−0.7 (3)
C21—P1—C31—C36	−86.92 (14)	C64—C65—C66—C61	0.2 (3)
Ag1—P1—C31—C36	38.18 (14)	C62—C61—C66—C65	0.4 (3)
C36—C31—C32—C33	0.1 (3)	P2—C61—C66—C65	−176.21 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.86	2.02	2.877 (2)	180
N1—H1B···O3ii	0.86	2.17	2.921 (2)	145
N2—H2···O1i	0.86	1.97	2.823 (2)	171
C35—H35···Cg2iii	0.93	2.97	3.746 (2)	142
C54—H54···Cg2iv	0.93	2.82	3.531 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.86	2.02	2.877 (2)	180
N1—H1B⋯O3ii	0.86	2.17	2.921 (2)	145
N2—H2⋯O1i	0.86	1.97	2.823 (2)	171
C35—H35⋯Cg2iii	0.93	2.97	3.746 (2)	142
C54—H54⋯Cg2iv	0.93	2.82	3.531 (2)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .