supplementary materials


lh5550 scheme

Acta Cryst. (2012). E68, m1506-m1507    [ doi:10.1107/S1600536812045199 ]

(1-Acetylthiourea-[kappa]S)bromidobis(triphenylphosphane-[kappa]P)silver(I)

C. Pakawatchai, P. Jantaramas, J. Mokhagul and R. Nimthong

Abstract top

In the title complex, [AgBr(C3H6N2OS)(C18H15P)2], the AgI ion is in a distorted tetrahedral geometry coordinated by two P atoms from two triphenylphosphane ligands, one S atom of an acetylthiourea ligand and one bromide ligand. There are intramolecular N-H...Br and N-H...O hydrogen bonds present. In the crystal, pairs of N-H...S hydrogen bonds involving thiourea groups form inversion dimers. In addition, moleclues pack to give sixfold phenyl embraces with an intermolecular P...P distance of 6.4586 (17) Å.

Comment top

The studies of silver(I) complexes with tertiary phosphane and sulfur donor ligands as co-ligainds has progressed extensively in recent years (Lobana et al., 2008; Nawaz et al., 2011) because of their potential applications such as antimicrobial activities (Isab et al., 2010) and they also often show interesting luminescence properties (Ferrari et al., 2007). Moreover, sixfold phenyl embraces (6PE), a common motif of the six phenyl groups of two adjacent triphenylphosphane (PPh3) ligands have been also widely studied, where six phenyl rings in the interaction zone participate in a concerted cycle of edge-to-face (ef) phenyl···phenyl interactions (Dance et al., 2000).

The molecular structure of the title compound (I) is shown in Fig. 1. In the mononuclear complex, the AgI ion exists in a distorted tetrahedral geometry. The Ag—P1 and Ag—P2 distances of 2.4807 (9) and 2.4657 (9) Å are closed to the values of [AgBr(–S-Hpytsc(Ph3P)2].CH3CN (Ag—P1 = 2.4605 (19), Ag—P2 = 2.4926 (19) Å) (Lobana et al., 2008). The observed Ag—S distance of 2.8789 (10) Å in (I) is appreciably longer than the mean value of 2.632 (1) Å for [Ag(PPh3)2(pytH)2]NO3 (Aslanidis et al., 1997). The P1—Ag—P2 angle of 124.52 (3)° approaches close to the average value found in compounds containing an AgI ion bound to two triphenylphosphanes e.g. in [Ag(1,2,4-L)(PPh3)2]n (HL = triazole) (P2—Ag—P1 = 126.29 (7)°) (Nomiya et al., 1998) and in [(Ph3P)2AgO3SCH3] (P2—Ag—P1 = 132.4 (4)°) (Zhang et al.,2008). There are intramolecular N2—H···Br and N1—H···O hydrogen bonds present. In the crystal, N and S atoms of the thiourea groups are invovled in forming hydrogen bonded dimers across an inversion center (symmetry code: -x + 1, -y + 1, -z + 1) and sixfold phenyl embraces with an intermolecular P···P distance of 6.4586 (17) Å are arranged in one-dimensional chains (Fig. 2).

Related literature top

For the definition of sixfold phenyl embraces, see: Dance et al. (2000). For the synthesis and structure of silver(I) coordination compounds and their potential applications, see: Ferrari et al. (2007); Lobana et al. (2008); Isab et al. (2010); Nawaz et al. (2011). For relevant examples of discrete complexes, see: Aslanidis et al. (1997); Nomiya et al. (1998); Lobana et al. (2008); Zhang et al. (2008).

Experimental top

Triphenylphosphane (0.28 g, 1.00 mmol) was dissolved in 30 cm3 of mixed sovents of acetonitrile and methanol at 343–348 K and then AgBr (0.10 g, 0.50 mmol) was added. The mixture was stirred for 2 h during that time a greenish precipitate was formed. Acetylthiourea (0.13 g, 1.00 mmol) was added and the new reaction mixture was heated under reflux for 5 h where upon the precipitate gradually disappeared. The resulting clear solution was filtered off and left to evaporate at room temperature. The crystalline solids, which were deposited upon standing for several days, were filtered off and dried in vacuo. Analysis found: C 57.58, H 4.09, N 3.27, S 2.37%; calculated for C39H32AgBrN2OP2S: C 56.40, H 4.37, N 3.37, S 3.86%.

Refinement top

The H atoms bonded to C atoms were constrained with a riding model of 0.93 Å (aryl H), and Uiso(H) = 1.2Ueq(C); 0.96 Å(CH3) and Uiso(H) = 1.5Ueq(C). All H atom bonded to the N atom was located in a difference Fourier map and refined isotropically.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Part of the crystal structure showing intermolecular hydrogen (red dashed lines) bond and six fold phenyl embraces shown as purple dashed lines.
(1-Acetylthiourea-κS)bromidobis(triphenylphosphane-κP)silver(I) top
Crystal data top
[AgBr(C3H6N2OS)(C18H15P)2]Z = 2
Mr = 830.48F(000) = 840
Triclinic, P1Dx = 1.521 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.4684 (12) ÅCell parameters from 4019 reflections
b = 12.9898 (14) Åθ = 2.3–21.9°
c = 14.8354 (16) ŵ = 1.84 mm1
α = 71.091 (2)°T = 293 K
β = 80.955 (3)°Hexagon, colorless
γ = 72.261 (2)°0.23 × 0.11 × 0.02 mm
V = 1813.9 (3) Å3
Data collection top
Bruker SMART CCD
diffractometer
8788 independent reflections
Radiation source: fine-focus sealed tube6789 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Frames, each covering 0.3 ° in ω scansθmax = 28.1°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1313
Tmin = 0.793, Tmax = 0.957k = 1717
25247 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0377P)2 + 0.3327P]
where P = (Fo2 + 2Fc2)/3
8788 reflections(Δ/σ)max = 0.006
434 parametersΔρmax = 0.86 e Å3
0 restraintsΔρmin = 0.47 e Å3
Crystal data top
[AgBr(C3H6N2OS)(C18H15P)2]γ = 72.261 (2)°
Mr = 830.48V = 1813.9 (3) Å3
Triclinic, P1Z = 2
a = 10.4684 (12) ÅMo Kα radiation
b = 12.9898 (14) ŵ = 1.84 mm1
c = 14.8354 (16) ÅT = 293 K
α = 71.091 (2)°0.23 × 0.11 × 0.02 mm
β = 80.955 (3)°
Data collection top
Bruker SMART CCD
diffractometer
8788 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
6789 reflections with I > 2σ(I)
Tmin = 0.793, Tmax = 0.957Rint = 0.046
25247 measured reflectionsθmax = 28.1°
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099Δρmax = 0.86 e Å3
S = 1.07Δρmin = 0.47 e Å3
8788 reflectionsAbsolute structure: ?
434 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2921 (3)0.4815 (3)0.4632 (2)0.0363 (8)
C20.1877 (4)0.3499 (3)0.4337 (3)0.0442 (9)
C30.0634 (4)0.3492 (4)0.3968 (3)0.0606 (12)
H3A0.03450.41730.34580.091*
H3B0.00620.34500.44730.091*
H3C0.08190.28490.37350.091*
C110.4784 (3)0.5721 (3)0.1742 (2)0.0351 (7)
C120.5091 (4)0.4991 (4)0.2650 (3)0.0578 (11)
H120.44360.46880.30530.069*
C130.6367 (5)0.4717 (4)0.2953 (3)0.0714 (14)
H130.65660.42380.35630.086*
C140.7332 (5)0.5144 (4)0.2361 (4)0.0726 (15)
H140.81830.49770.25720.087*
C150.7052 (4)0.5817 (4)0.1460 (4)0.0688 (14)
H150.77260.60800.10490.083*
C160.5786 (4)0.6112 (3)0.1150 (3)0.0498 (10)
H160.56080.65800.05340.060*
C210.2525 (3)0.5013 (3)0.1451 (2)0.0354 (8)
C220.3421 (4)0.3957 (3)0.1521 (3)0.0504 (10)
H220.43140.38270.16360.060*
C230.2986 (5)0.3098 (3)0.1421 (3)0.0618 (12)
H230.35900.23910.14740.074*
C240.1689 (5)0.3270 (3)0.1245 (3)0.0562 (11)
H240.14150.26900.11640.067*
C250.0787 (4)0.4309 (4)0.1189 (3)0.0542 (10)
H250.01020.44320.10700.065*
C260.1194 (4)0.5168 (3)0.1309 (3)0.0463 (9)
H260.05700.58580.12950.056*
C310.3048 (3)0.7054 (3)0.0206 (2)0.0328 (7)
C320.2915 (4)0.6632 (3)0.0513 (3)0.0430 (9)
H320.28320.59010.03610.052*
C330.2906 (4)0.7293 (4)0.1451 (3)0.0540 (10)
H330.27940.70110.19260.065*
C340.3062 (4)0.8366 (3)0.1691 (3)0.0537 (10)
H340.30680.88030.23260.064*
C350.3209 (4)0.8786 (3)0.0989 (3)0.0524 (10)
H350.33210.95080.11480.063*
C360.3189 (4)0.8133 (3)0.0038 (3)0.0433 (9)
H360.32710.84270.04370.052*
C410.0368 (3)0.9939 (3)0.3172 (2)0.0302 (7)
C420.0004 (4)1.1104 (3)0.3034 (3)0.0411 (8)
H420.04791.15530.25730.049*
C430.1053 (4)1.1592 (3)0.3575 (3)0.0457 (9)
H430.12931.23700.34750.055*
C440.1755 (4)1.0938 (3)0.4262 (3)0.0491 (10)
H440.24551.12680.46360.059*
C450.1417 (4)0.9795 (3)0.4393 (3)0.0487 (9)
H450.19050.93540.48480.058*
C460.0356 (3)0.9293 (3)0.3853 (2)0.0387 (8)
H460.01310.85170.39510.046*
C510.1781 (3)1.0222 (2)0.1304 (2)0.0301 (7)
C520.0624 (4)1.0633 (3)0.0812 (3)0.0438 (9)
H520.01631.04520.11090.053*
C530.0641 (4)1.1315 (3)0.0127 (3)0.0516 (10)
H530.01401.15890.04540.062*
C540.1780 (4)1.1589 (3)0.0578 (3)0.0515 (10)
H540.17821.20410.12090.062*
C550.2930 (4)1.1189 (3)0.0090 (3)0.0473 (9)
H550.37121.13770.03920.057*
C560.2931 (3)1.0513 (3)0.0842 (2)0.0363 (8)
H560.37151.02480.11650.044*
C610.3312 (3)0.9188 (3)0.2940 (2)0.0362 (8)
C620.3421 (4)0.9981 (4)0.3328 (3)0.0518 (10)
H620.26601.05440.34210.062*
C630.4655 (5)0.9950 (5)0.3584 (3)0.0730 (14)
H630.47201.04790.38600.088*
C640.5777 (5)0.9131 (5)0.3424 (3)0.0753 (16)
H640.66070.91160.35850.090*
C650.5697 (4)0.8343 (4)0.3034 (3)0.0675 (14)
H650.64680.77980.29230.081*
C660.4461 (4)0.8355 (3)0.2802 (3)0.0497 (10)
H660.43980.78020.25530.060*
N10.3869 (4)0.3971 (3)0.5087 (3)0.0552 (10)
N20.1933 (3)0.4553 (2)0.4313 (2)0.0374 (7)
O0.2771 (3)0.2643 (2)0.4627 (2)0.0635 (8)
P10.30183 (8)0.62370 (7)0.14657 (6)0.03201 (19)
P20.17669 (8)0.92148 (7)0.25006 (6)0.03023 (19)
Br0.05776 (3)0.67299 (3)0.31620 (3)0.04306 (11)
Ag0.17151 (3)0.73006 (2)0.258501 (19)0.03744 (9)
S0.28951 (9)0.61787 (8)0.43976 (7)0.0431 (2)
H1A0.450 (4)0.408 (3)0.529 (3)0.052*
H1B0.382 (4)0.331 (3)0.517 (3)0.052*
H20.128 (4)0.515 (3)0.404 (3)0.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0368 (18)0.046 (2)0.0252 (17)0.0178 (16)0.0045 (14)0.0012 (15)
C20.054 (2)0.042 (2)0.038 (2)0.0211 (19)0.0063 (17)0.0033 (17)
C30.067 (3)0.055 (3)0.068 (3)0.031 (2)0.023 (2)0.008 (2)
C110.0319 (17)0.0379 (19)0.038 (2)0.0045 (15)0.0027 (15)0.0193 (16)
C120.046 (2)0.077 (3)0.038 (2)0.004 (2)0.0008 (18)0.019 (2)
C130.060 (3)0.094 (4)0.049 (3)0.015 (3)0.020 (2)0.033 (3)
C140.050 (3)0.077 (3)0.108 (4)0.001 (2)0.040 (3)0.051 (3)
C150.039 (2)0.055 (3)0.112 (4)0.015 (2)0.012 (3)0.018 (3)
C160.038 (2)0.044 (2)0.065 (3)0.0131 (17)0.0085 (19)0.0074 (19)
C210.0371 (18)0.0353 (18)0.0341 (19)0.0126 (15)0.0032 (15)0.0106 (15)
C220.042 (2)0.039 (2)0.066 (3)0.0064 (17)0.0017 (19)0.0162 (19)
C230.073 (3)0.032 (2)0.076 (3)0.010 (2)0.005 (2)0.020 (2)
C240.072 (3)0.047 (2)0.060 (3)0.035 (2)0.017 (2)0.022 (2)
C250.051 (2)0.064 (3)0.061 (3)0.030 (2)0.004 (2)0.024 (2)
C260.040 (2)0.043 (2)0.059 (2)0.0098 (17)0.0002 (18)0.0212 (19)
C310.0282 (16)0.0327 (17)0.0338 (18)0.0023 (14)0.0004 (14)0.0112 (14)
C320.051 (2)0.039 (2)0.039 (2)0.0110 (17)0.0039 (17)0.0128 (17)
C330.057 (3)0.061 (3)0.047 (2)0.010 (2)0.0082 (19)0.023 (2)
C340.054 (2)0.053 (3)0.040 (2)0.006 (2)0.0013 (19)0.0033 (19)
C350.065 (3)0.037 (2)0.050 (2)0.0157 (19)0.000 (2)0.0058 (18)
C360.051 (2)0.037 (2)0.045 (2)0.0139 (17)0.0014 (17)0.0160 (17)
C410.0274 (16)0.0327 (17)0.0319 (17)0.0072 (13)0.0041 (13)0.0113 (14)
C420.044 (2)0.0351 (19)0.044 (2)0.0126 (16)0.0033 (17)0.0086 (16)
C430.050 (2)0.035 (2)0.053 (2)0.0031 (17)0.0079 (19)0.0191 (18)
C440.045 (2)0.064 (3)0.046 (2)0.011 (2)0.0046 (18)0.032 (2)
C450.048 (2)0.063 (3)0.041 (2)0.026 (2)0.0097 (18)0.0187 (19)
C460.046 (2)0.0371 (19)0.0350 (19)0.0133 (16)0.0032 (16)0.0136 (15)
C510.0344 (17)0.0227 (15)0.0321 (17)0.0071 (13)0.0026 (14)0.0071 (13)
C520.038 (2)0.049 (2)0.044 (2)0.0086 (17)0.0066 (16)0.0130 (18)
C530.053 (2)0.050 (2)0.047 (2)0.0028 (19)0.022 (2)0.0093 (19)
C540.073 (3)0.041 (2)0.035 (2)0.012 (2)0.008 (2)0.0046 (17)
C550.053 (2)0.042 (2)0.042 (2)0.0199 (18)0.0059 (18)0.0045 (17)
C560.0356 (18)0.0343 (18)0.039 (2)0.0118 (15)0.0044 (15)0.0078 (15)
C610.0359 (18)0.0413 (19)0.0273 (17)0.0137 (16)0.0052 (14)0.0003 (15)
C620.051 (2)0.064 (3)0.045 (2)0.022 (2)0.0082 (18)0.014 (2)
C630.079 (3)0.092 (4)0.061 (3)0.048 (3)0.023 (3)0.010 (3)
C640.056 (3)0.094 (4)0.067 (3)0.039 (3)0.033 (2)0.018 (3)
C650.040 (2)0.069 (3)0.070 (3)0.017 (2)0.014 (2)0.017 (2)
C660.038 (2)0.046 (2)0.053 (2)0.0088 (17)0.0085 (18)0.0016 (18)
N10.057 (2)0.046 (2)0.059 (2)0.0193 (18)0.0294 (18)0.0071 (17)
N20.0371 (16)0.0326 (16)0.0386 (17)0.0117 (13)0.0124 (13)0.0014 (13)
O0.069 (2)0.0395 (16)0.078 (2)0.0117 (15)0.0264 (17)0.0056 (15)
P10.0298 (4)0.0328 (5)0.0343 (5)0.0073 (4)0.0003 (4)0.0129 (4)
P20.0297 (4)0.0281 (4)0.0315 (5)0.0083 (3)0.0012 (3)0.0068 (3)
Br0.02998 (18)0.0510 (2)0.0468 (2)0.01327 (16)0.00403 (15)0.00963 (17)
Ag0.03723 (15)0.03262 (15)0.04341 (17)0.01155 (11)0.00531 (11)0.01416 (12)
S0.0478 (5)0.0414 (5)0.0426 (5)0.0164 (4)0.0160 (4)0.0054 (4)
Geometric parameters (Å, º) top
C1—N11.308 (4)C36—H360.9300
C1—N21.373 (4)C41—C461.377 (4)
C1—S1.683 (4)C41—C421.397 (4)
C2—O1.216 (4)C41—P21.825 (3)
C2—N21.377 (4)C42—C431.376 (5)
C2—C31.492 (5)C42—H420.9300
C3—H3A0.9600C43—C441.373 (5)
C3—H3B0.9600C43—H430.9300
C3—H3C0.9600C44—C451.372 (5)
C11—C161.369 (5)C44—H440.9300
C11—C121.393 (5)C45—C461.385 (5)
C11—P11.828 (3)C45—H450.9300
C12—C131.381 (6)C46—H460.9300
C12—H120.9300C51—C561.383 (4)
C13—C141.360 (7)C51—C521.385 (4)
C13—H130.9300C51—P21.833 (3)
C14—C151.358 (7)C52—C531.388 (5)
C14—H140.9300C52—H520.9300
C15—C161.372 (5)C53—C541.361 (6)
C15—H150.9300C53—H530.9300
C16—H160.9300C54—C551.375 (5)
C21—C261.385 (5)C54—H540.9300
C21—C221.388 (5)C55—C561.378 (5)
C21—P11.822 (3)C55—H550.9300
C22—C231.383 (5)C56—H560.9300
C22—H220.9300C61—C621.371 (5)
C23—C241.359 (6)C61—C661.390 (5)
C23—H230.9300C61—P21.823 (3)
C24—C251.377 (6)C62—C631.388 (6)
C24—H240.9300C62—H620.9300
C25—C261.379 (5)C63—C641.372 (7)
C25—H250.9300C63—H630.9300
C26—H260.9300C64—C651.357 (7)
C31—C361.377 (5)C64—H640.9300
C31—C321.390 (5)C65—C661.385 (5)
C31—P11.827 (3)C65—H650.9300
C32—C331.377 (5)C66—H660.9300
C32—H320.9300N1—H1A0.84 (4)
C33—C341.377 (6)N1—H1B0.84 (4)
C33—H330.9300N2—H20.89 (4)
C34—C351.369 (6)P1—Ag2.4807 (9)
C34—H340.9300P2—Ag2.4657 (9)
C35—C361.392 (5)Br—Ag2.6588 (5)
C35—H350.9300Ag—S2.8789 (10)
N1—C1—N2117.2 (3)C44—C43—H43119.8
N1—C1—S123.2 (3)C42—C43—H43119.8
N2—C1—S119.6 (3)C45—C44—C43119.6 (3)
O—C2—N2122.8 (3)C45—C44—H44120.2
O—C2—C3122.6 (4)C43—C44—H44120.2
N2—C2—C3114.5 (3)C44—C45—C46120.5 (4)
C2—C3—H3A109.5C44—C45—H45119.7
C2—C3—H3B109.5C46—C45—H45119.7
H3A—C3—H3B109.5C41—C46—C45120.3 (3)
C2—C3—H3C109.5C41—C46—H46119.8
H3A—C3—H3C109.5C45—C46—H46119.8
H3B—C3—H3C109.5C56—C51—C52118.6 (3)
C16—C11—C12118.6 (3)C56—C51—P2122.6 (2)
C16—C11—P1123.5 (3)C52—C51—P2118.6 (3)
C12—C11—P1117.5 (3)C51—C52—C53119.9 (3)
C13—C12—C11120.0 (4)C51—C52—H52120.1
C13—C12—H12120.0C53—C52—H52120.1
C11—C12—H12120.0C54—C53—C52121.1 (4)
C14—C13—C12120.1 (4)C54—C53—H53119.4
C14—C13—H13119.9C52—C53—H53119.4
C12—C13—H13119.9C53—C54—C55119.3 (4)
C15—C14—C13119.9 (4)C53—C54—H54120.4
C15—C14—H14120.0C55—C54—H54120.4
C13—C14—H14120.0C54—C55—C56120.4 (3)
C14—C15—C16120.8 (5)C54—C55—H55119.8
C14—C15—H15119.6C56—C55—H55119.8
C16—C15—H15119.6C55—C56—C51120.8 (3)
C11—C16—C15120.4 (4)C55—C56—H56119.6
C11—C16—H16119.8C51—C56—H56119.6
C15—C16—H16119.8C62—C61—C66118.9 (3)
C26—C21—C22118.5 (3)C62—C61—P2124.0 (3)
C26—C21—P1117.7 (3)C66—C61—P2116.9 (3)
C22—C21—P1123.6 (3)C61—C62—C63120.7 (4)
C23—C22—C21119.9 (4)C61—C62—H62119.7
C23—C22—H22120.0C63—C62—H62119.7
C21—C22—H22120.0C64—C63—C62119.3 (5)
C24—C23—C22121.2 (4)C64—C63—H63120.4
C24—C23—H23119.4C62—C63—H63120.4
C22—C23—H23119.4C65—C64—C63121.2 (4)
C23—C24—C25119.4 (4)C65—C64—H64119.4
C23—C24—H24120.3C63—C64—H64119.4
C25—C24—H24120.3C64—C65—C66119.6 (5)
C24—C25—C26120.3 (4)C64—C65—H65120.2
C24—C25—H25119.9C66—C65—H65120.2
C26—C25—H25119.9C65—C66—C61120.4 (4)
C25—C26—C21120.6 (4)C65—C66—H66119.8
C25—C26—H26119.7C61—C66—H66119.8
C21—C26—H26119.7C1—N1—H1A121 (3)
C36—C31—C32118.9 (3)C1—N1—H1B118 (3)
C36—C31—P1118.8 (3)H1A—N1—H1B121 (4)
C32—C31—P1122.3 (3)C1—N2—C2127.6 (3)
C33—C32—C31120.2 (3)C1—N2—H2114 (2)
C33—C32—H32119.9C2—N2—H2118 (2)
C31—C32—H32119.9C21—P1—C31102.81 (15)
C34—C33—C32120.7 (4)C21—P1—C11106.31 (15)
C34—C33—H33119.7C31—P1—C11104.27 (15)
C32—C33—H33119.7C21—P1—Ag117.41 (11)
C35—C34—C33119.7 (4)C31—P1—Ag115.68 (10)
C35—C34—H34120.2C11—P1—Ag109.20 (11)
C33—C34—H34120.2C61—P2—C41107.17 (15)
C34—C35—C36120.0 (4)C61—P2—C51101.85 (14)
C34—C35—H35120.0C41—P2—C51104.63 (14)
C36—C35—H35120.0C61—P2—Ag111.47 (12)
C31—C36—C35120.6 (3)C41—P2—Ag114.18 (10)
C31—C36—H36119.7C51—P2—Ag116.42 (10)
C35—C36—H36119.7P2—Ag—P1124.52 (3)
C46—C41—C42118.7 (3)P2—Ag—Br118.59 (2)
C46—C41—P2117.8 (2)P1—Ag—Br108.96 (2)
C42—C41—P2123.5 (3)P2—Ag—S96.12 (3)
C43—C42—C41120.4 (3)P1—Ag—S106.75 (3)
C43—C42—H42119.8Br—Ag—S95.21 (2)
C41—C42—H42119.8C1—S—Ag104.87 (12)
C44—C43—C42120.4 (3)
C16—C11—C12—C133.0 (6)C26—C21—P1—Ag53.9 (3)
P1—C11—C12—C13169.7 (3)C22—C21—P1—Ag129.8 (3)
C11—C12—C13—C141.0 (7)C36—C31—P1—C21170.3 (3)
C12—C13—C14—C151.9 (7)C32—C31—P1—C218.7 (3)
C13—C14—C15—C162.8 (7)C36—C31—P1—C1178.9 (3)
C12—C11—C16—C152.1 (6)C32—C31—P1—C11102.0 (3)
P1—C11—C16—C15170.1 (3)C36—C31—P1—Ag41.1 (3)
C14—C15—C16—C110.7 (7)C32—C31—P1—Ag138.0 (3)
C26—C21—C22—C232.0 (6)C16—C11—P1—C21120.5 (3)
P1—C21—C22—C23174.4 (3)C12—C11—P1—C2167.2 (3)
C21—C22—C23—C240.5 (7)C16—C11—P1—C3112.2 (3)
C22—C23—C24—C251.5 (7)C12—C11—P1—C31175.4 (3)
C23—C24—C25—C260.0 (6)C16—C11—P1—Ag112.0 (3)
C24—C25—C26—C212.5 (6)C12—C11—P1—Ag60.4 (3)
C22—C21—C26—C253.5 (6)C62—C61—P2—C4127.7 (3)
P1—C21—C26—C25173.1 (3)C66—C61—P2—C41157.2 (3)
C36—C31—C32—C330.9 (5)C62—C61—P2—C5181.9 (3)
P1—C31—C32—C33178.2 (3)C66—C61—P2—C5193.2 (3)
C31—C32—C33—C341.6 (6)C62—C61—P2—Ag153.3 (3)
C32—C33—C34—C350.9 (6)C66—C61—P2—Ag31.6 (3)
C33—C34—C35—C360.5 (6)C46—C41—P2—C61106.6 (3)
C32—C31—C36—C350.5 (5)C42—C41—P2—C6173.0 (3)
P1—C31—C36—C35179.6 (3)C46—C41—P2—C51145.7 (3)
C34—C35—C36—C311.2 (6)C42—C41—P2—C5134.6 (3)
C46—C41—C42—C430.5 (5)C46—C41—P2—Ag17.3 (3)
P2—C41—C42—C43179.2 (3)C42—C41—P2—Ag163.1 (2)
C41—C42—C43—C440.5 (6)C56—C51—P2—C6118.1 (3)
C42—C43—C44—C451.5 (6)C52—C51—P2—C61167.6 (3)
C43—C44—C45—C461.5 (6)C56—C51—P2—C41129.6 (3)
C42—C41—C46—C450.5 (5)C52—C51—P2—C4156.1 (3)
P2—C41—C46—C45179.2 (3)C56—C51—P2—Ag103.3 (3)
C44—C45—C46—C410.5 (6)C52—C51—P2—Ag70.9 (3)
C56—C51—C52—C530.3 (5)C61—P2—Ag—P175.65 (12)
P2—C51—C52—C53174.1 (3)C41—P2—Ag—P1162.73 (11)
C51—C52—C53—C540.1 (6)C51—P2—Ag—P140.57 (12)
C52—C53—C54—C550.5 (6)C61—P2—Ag—Br138.88 (12)
C53—C54—C55—C560.4 (6)C41—P2—Ag—Br17.26 (12)
C54—C55—C56—C510.0 (5)C51—P2—Ag—Br104.90 (11)
C52—C51—C56—C550.4 (5)C61—P2—Ag—S39.53 (12)
P2—C51—C56—C55173.8 (3)C41—P2—Ag—S82.09 (11)
C66—C61—C62—C630.3 (6)C51—P2—Ag—S155.75 (12)
P2—C61—C62—C63175.3 (3)C21—P1—Ag—P2164.49 (13)
C61—C62—C63—C641.5 (7)C31—P1—Ag—P242.71 (13)
C62—C63—C64—C651.0 (7)C11—P1—Ag—P274.48 (13)
C63—C64—C65—C660.7 (7)C21—P1—Ag—Br16.24 (13)
C64—C65—C66—C612.0 (6)C31—P1—Ag—Br105.53 (12)
C62—C61—C66—C651.5 (5)C11—P1—Ag—Br137.27 (12)
P2—C61—C66—C65173.9 (3)C21—P1—Ag—S85.51 (13)
N1—C1—N2—C26.3 (5)C31—P1—Ag—S152.72 (12)
S—C1—N2—C2171.7 (3)C11—P1—Ag—S35.52 (12)
O—C2—N2—C13.1 (6)N1—C1—S—Ag146.3 (3)
C3—C2—N2—C1177.6 (4)N2—C1—S—Ag31.6 (3)
C26—C21—P1—C3174.3 (3)P2—Ag—S—C1178.26 (12)
C22—C21—P1—C31102.0 (3)P1—Ag—S—C152.88 (13)
C26—C21—P1—C11176.4 (3)Br—Ag—S—C158.72 (12)
C22—C21—P1—C117.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Si0.84 (4)2.74 (4)3.524 (4)158 (3)
N1—H1B···O0.84 (4)1.99 (4)2.642 (5)135 (4)
N2—H2···Br0.89 (4)2.52 (4)3.402 (3)174 (3)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Si0.84 (4)2.74 (4)3.524 (4)158 (3)
N1—H1B···O0.84 (4)1.99 (4)2.642 (5)135 (4)
N2—H2···Br0.89 (4)2.52 (4)3.402 (3)174 (3)
Symmetry code: (i) x+1, y+1, z+1.
Acknowledgements top

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

references
References top

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