(N-Phenyl­thio­urea-κS)bis­(tri­phenylphosphane-κP)silver(I) nitrate

Mekarat, S.; Pakawatchai, C.; Saithong, S.

doi:10.1107/S1600536814014147

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Pages m281-m282

https://doi.org/10.1107/S1600536814014147

Open

access

(N-Phenylthiourea-κS)bis(triphenylphosphane-κP)silver(I) nitrate

Sofia Mekarat,^a Chaveng Pakawatchai ^b ^* and Saowanit Saithong ^b

^aFaculty of Science and Technology, Princess of Naradhiwas University, Narathiwat, 96000, Thailand, and ^bDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: chaveng.p@psu.ac.th

(Received 11 June 2014; accepted 17 June 2014; online 25 June 2014)

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 tetramers (two cations and two anions), which feature R₂²(8) and R₄⁴(8) loops. The cations are linked by weak C—H⋯π interactions, generating a three-dimensional network.

Keywords: N-phenylthiourea; triphenylphosphane; silver(I)nitrate; crystal structure.

CCDC reference: 1008627

Related literature

For properties of mixed-ligand d¹⁰ 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_r = 846.63
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.064
S = 1.05
9196 reflections
478 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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⋯Cg2^iv	0.93	2.82	3.531 (2)	134
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+2; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) -x+1, -y+2, -z+2.

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).

Supporting information

CCDC reference: 1008627

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536814014147/hb7242sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814014147/hb7242Isup2.hkl

checkCIF report

Chemical context top

Mixed-ligand complexes of group 11 metals dispaly many properties such as magnetism (Oshio et al., 1996); microporousity (Zheng et al., 2001); luminescence (Sewead et al., 2003) and antimicrobial activities (Isab et al.,2010). In our earlier work, we synthesized and characterized the neutral monomeric copper(I) complex containing mixed ligands of triphenylphosphane (PPh₃: C₁₈H₁₅P) and N-phynylthiourea (ptu : C₇H₈N₂S), [CuI(ptu)(PPh₃)₂] (Nimthong et al., 2008). As part of our continuing studies in this area, we now describe the synthesis and structure of the title compound, [Ag(ptu)(PPh₃)₂]NO₃ (Scheme I).

Structural commentary top

Unlike the previous complex mentioned above (Nimthong et al., 2008), this complex is an ionic complex and it crystallizes in monoclinic system space group P2₁/c. The structure consists of the discrete mononuclear [Ag(ptu)(PPh₃)₂]⁺cation and the NO₃^- anion which is similar to those [Ag(PPh₃)₂(pymtH)]NO₃ (Aslanidis et al., 1997). A perspective view of the molecular structure of [Ag(ptu)(PPh₃)₂]NO₃ with atomic labeling is given in Figure 1. The cation part contains silver(I) atom trigonally coordinated by two phosphorus atoms from two triphenylphosphane molecules and one sulfur atom from N–phenylthiourea molecule similar to found in those silver oxyanion complexes containing mixed PPh₃/heterocyclic thione ligands (Aslanidis et al., 1997; Ghassemzadeh et al., 2004). The Ag–P bond lengths of 2.4645 (5) and 2.4693 (4)Å are similar to the values of 2.455 (1) and 2.447 (1) Å observed in [Ag(PPh₃)₂(pymtH)]NO₃ (Aslanidis et al., 1997), however, these values are slightly different from the values of 2.458 (2) and 2.507 (2) Å compared to [Ag(TAMTTO)(PPh₃)₂]NO₃.1.5THF (Ghassemzadeh et al., 2004) because of the massive and steric effect of TAMTTO heterocyclic ligand. The Ag–S bond length [2.5307 (7) Å] is shorter than in those complexes [Ag(PPh₃)₂(pymtH)]NO₃ [2.573 (1)Å] and [Ag(TAMTTO)(PPh₃)₂]NO₃.1.5 THF [2.592 (2) Å] (Aslanidis et al., 1997; Ghassemzadeh et al., 2004 ). The P(1)–Ag–P(2), P(1)–Ag–S(1) and P(2)–Ag–S(1) bond angles are 127.55 (1)° ,113.02 (1)° and 112.69 (1)°, respectively. Due to the steric crowding of six phenyl rings from two bulky triphenyl phosphane ligands and the π(CH)···Ag interaction [3.314 Å] between the centriod of phenyl ring (C2—C7) of the N–phenylthiourea and metal atom, the silver centre atom deviates from idealized trigonal planar with this atom lying ca 0.372 (1) Å out of the P₂S plane. For the anion, although the oxygen atoms of the nitrate have no influence on coordination, they have great influence on the crystal packing of the complex. It is nearly planar with the bond angles around the nitrogen atom ranging from 119.01 (1)-120.53 (1)° and N(3)–O bond distances are 1.231 (2) – 1.264 (2) Å.

Supramolecular features top

For the crystal packing, each [Ag(ptu)(PPh₃)₂]⁺ cation is connected to another adjacent cationic part via hydrogen bonding interactions, N–H···O, which are observed between amino and amide groups and nitrate oxygen atoms generate a cyclic hydrogen bond interactions, two R₂²(8) graph sets for cationic-anionic interactions and one R₄⁴(8) graph set for anionic-anionic interaction, [ N(1)–H(1A)···O(3)ⁱ : 2.877 (2)Å, N(1)–H(1B)···O(3)ⁱⁱ : 2.921 (2)Å, N(2)–H(2)···O(1) : 2.823 (2) Å and symmetry code : (i) x-1,y,z, (ii) -x+1,-y+1,-z+2] as depicted in Figure 2 and 3. In addition, the cationic parts are linked together by the CH···π interactions between the phenyl rings with the distance of 3.746 (2) Å for C35–H35···Cg2 and 3.531 (2) Å for C54–H54···Cg2 [Cg2 : C11–C16] generating the three dimensional supramolecular network. All interactions are depicted in Figure 4.

Synthesis and crystallization top

The mixture silver(I) nitrate and triphenylphosphane in ethanol was refluxed at the temperature ca 60-70 ^°C for 2 h. After that, N-phenylthiourea ligand was added to the clear mixture solution and then continued to reflux futher for 3 h. The clear filtration was kept and left to evaporate slowly at ambient temperature. After several days, colorless blocks were obtained. The melting point of the complex is 192-194 ^°C . Elemental analysis,calculated for [Ag(PPh₃)₂(ptu)]NO₃ : C, 60.99;H, 4.52; N, 4.96; S, 3.78%, found: C, 65.16; H, 4.96; N, 5.16; S, 4.04%.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The structures were solved by direct methods and refined by a full-matrix least-squares procedure based on F². All hydrogen atoms were placed in geometrically idealised positions and refined isotropically with a riding model for both of amine N [N—H = 0.86 Å and with U_i_so(H) =1.2U_eq(N)] and phenyl ring C-sp²[C—H = 0.93 Å and with U_i_so(H) = 1.2U_eq(C)]. ;

Related literature top

For properties of mixed-ligand d¹⁰ 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).

Structure description top

For properties of mixed-ligand d¹⁰ 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).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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).

Figures top

	Fig. 1. The molecular structure of [Ag(ptu)(PPh₃)₂]NO₃ complex. Displacement ellipsoids are shown at 50% probability level.
	Fig. 2. The hydrogen bonding interactions of [Ag(ptu)(PPh₃)₂]NO₃ complex (#i: x - 1, y, z, #ii: 1 - x, 1 - y, 2 - z, #iii: -x, 1 - y,2 - z).
	Fig. 3. The cyclic of hydrogen bonding interactions containing two R₂²(8) and one R₄⁴(8).
	Fig. 4. The three-dimensional supramolecular interactions in crystal packing.

(N-Phenylthiourea-κS)bis(triphenylphosphane-κP)silver(I) nitrate top

Crystal data top

[Ag(C₇H₈N₂S)(C₁₈H₁₅P)₂]NO₃	F(000) = 1736
M_r = 846.63	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0264P)² + 2.6456P] where P = (F_o² + 2F_c²)/3
9196 reflections	(Δ/σ)_max = 0.003
478 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Ag(C₇H₈N₂S)(C₁₈H₁₅P)₂]NO₃	V = 3808.3 (2) Å³
M_r = 846.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.6113 (5) Å	µ = 0.71 mm⁻¹
b = 10.6431 (4) Å	T = 173 K
c = 26.4365 (10) Å	0.27 × 0.14 × 0.08 mm
β = 96.068 (1)°

Data collection top

Bruker SMART CCD diffractometer	9196 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	8261 reflections with I > 2σ(I)
T_min = 0.863, T_max = 1.000	R_int = 0.033
44417 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.05	Δρ_max = 0.55 e Å⁻³
9196 reflections	Δρ_min = −0.26 e Å⁻³
478 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg2^iv	0.93	2.82	3.531 (2)	134

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

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···Cg2^iv	0.93	2.82	3.531 (2)	134

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, −y+2, −z+2.

Acknowledgements

Financial support from the Center of Excellent for Innovation in Chemistry (PERCH–CIC), Office of the Higher Education Commission, Ministry of Education and Graduate School, Prince of Songkla University, are gratefully acknowledged.

References

Aslanidis, P., Karagiannidis, P., Akrivos, P. D., Krebs, B. & Lage, M. (1997). Inorg. Chim. Acta, 254, 277–284. CSD CrossRef CAS Web of Science Google Scholar
Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ghassemzadeh, M., Sharifi, A., Malakootikhah, J., Neumuller, B. & Iravani, E. (2004). Inorg. Chim. Acta, 357, 2245–2252. Web of Science CSD CrossRef CAS Google Scholar
Isab, A. A., Nawaz, S., Saleem, M., Altaf, M., Monim-ul-Mehboob, M., Ahmad, S. & Evans, H. (2010). Polyhedron, 29, 1251–1256. Web of Science CSD CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nimthong, R., Pakawatchai, C., Saithong, S. & Charmant, J. P. H. (2008). Acta Cryst. E64, m977. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oshio, H., Watanabe, T., Ohto, A., Ito, T. & Masuda, H. (1996). Inorg. Chem. 35, 472–479. CSD CrossRef PubMed CAS Web of Science Google Scholar
Sewead, C., Chan, J., Song, D. & Wang, S. (2003). Inorg. Chem. 42, 1112–1120. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Skoulika, S., Aubry, A., Karagiannidis, P., Aslanidis, P. & Papastefanou, S. (1991). Inorg. Chim. Acta, 183, 207–211. CSD CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zheng, S.-L., Tong, M.-L., Fu, R.-W., Chen, X.-M. & Ng, S.-W. (2001). Inorg. Chem. 40, 3562–3569. Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Pages m281-m282

https://doi.org/10.1107/S1600536814014147

Open

access