Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113000322/eg3103sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113000322/eg3103HLsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113000322/eg3103Isup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113000322/eg3103IIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113000322/eg3103IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113000322/eg3103Vsup6.hkl |
CCDC references: 925753; 925754; 925755; 925756; 925757
For related literature, see: Allen (2002); Altaf & Stoeckli-Evans (2012); Aoki & Saenger (1983, 1984); Bagautdinov et al. (2005); Bernstein et al. (1995); Brady et al. (1966); Brese & O'Keeffe (1991); Brown (2002); DeTitta, Edmonds, Stallings & Donohue (1976); DeTitta, Parthasarathy, Blessing & Stallings (1980); Farrugia (2012); Flack (1983); Goodwin et al. (1998); Griesser et al. (1973); Hadjiliadis & Pneumatikakis (1979); Kitajgorodskij (1973); Knowles (1989); Lett & Marquet (1971); Moss & Lane (1971); Nardelli (1999); Sigel et al. (1969); Spek (2009); Wood & Zwolinski (1976).
For the synthesis of (I), an equimolar (0.1 mmol) ratio of biotin to silver acetate in methanol–water (4:1 v/v, 20 ml) at room temperature, with continuous stirring for 30 min, was used, together with five drops of aqueous ammonia. The solution was then filtered and left undisturbed for crystallization by slow evaporation. The syntheses of (II) and (III) were carried out by dissolving equimolar amounts (0.1 mmol) of biotin and silver nitrate for (II), or silver perchlorate for (III), in methanol–water (4:1 v/v, 20 ml) at room temperature with continuous stirring for 30 min. The solutions were then filtered and left undisturbed for crystallization by slow evaporation. After approximately 5 d, colourless rod-like crystals of both complexes were obtained. The syntheses of (IV) and (V) were carried out in a similar manner using the silver salts AgPF6 and AgSbF6, respectively, but with a biotin-to-silver-salt molar ratio of 1:2. Warning! perchlorate salts are potentially explosive and should be handled with care and used in only very small quantities.
The absolute configurations of biotin and complexes (I), (II), (IV) and (V) were confirmed crystallographically by resonant scattering. The coordinates of each compound correspond to the absolute structure of the molecule in the crystal. In (I), one of the carboxyl O atoms (O1) exhibited a very elongated displacement ellipsoid. It was decided to split this atom (O1A/O1B) and it was refined with a fixed occupancy ratio of 0.6:0.4. For all compounds, the N-bound H atoms were located in difference electron-density maps and refined with distance restraints of N—H = 0.88 (2) Å, and with Uiso(H) = 1.2Ueq(N). The OH and C-bound H atoms were included in calculated positions and treated as riding atoms, with O—H = 0.84 Å and with Uiso(H) = 1.5Ueq(O), or with C—H = 1.00 and 0.99 Å for CH and CH2 H atoms, respectively, and with Uiso(H) = 1.2Ueq(C). The water H atoms on OW1 in (I) and those in (II) were located in difference Fourier maps. The H atoms on OW2 and OW3 in (I) were included in calculated positions using the method developed by Nardelli (1999) and implemented in WinGX (Farrugia, 2012). They were all refined with O—H distance restraints of 0.84 (2) Å, and for (I) with H···H = 1.45 (2) Å. For (I), (II) and (IV), a certain number of reflections were omitted using the OMIT instruction [In which software? Reference?]. These reflections were either affected by the beam stop at very low θ values or they were the most disagreeable reflections where Δ(F2)/e.s.d. was greater than 5.0–6.0.
For all compounds, data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C10H16N2O3S | F(000) = 520 |
Mr = 244.31 | Dx = 1.448 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4899 reflections |
a = 5.1955 (6) Å | θ = 1.9–26.1° |
b = 10.3017 (17) Å | µ = 0.28 mm−1 |
c = 20.943 (2) Å | T = 173 K |
V = 1120.9 (2) Å3 | Rod, colourless |
Z = 4 | 0.50 × 0.13 × 0.13 mm |
Stoe IPDS 2 diffractometer | 2102 independent reflections |
Radiation source: fine-focus sealed tube | 1871 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ϕ and ω rotation scans | θmax = 25.6°, θmin = 2.2° |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | h = −6→5 |
Tmin = 0.841, Tmax = 1.000 | k = −12→10 |
3715 measured reflections | l = −25→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0601P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
2102 reflections | Δρmax = 0.23 e Å−3 |
152 parameters | Δρmin = −0.25 e Å−3 |
2 restraints | Absolute structure: Flack (1983), with 837 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (9) |
C10H16N2O3S | V = 1120.9 (2) Å3 |
Mr = 244.31 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.1955 (6) Å | µ = 0.28 mm−1 |
b = 10.3017 (17) Å | T = 173 K |
c = 20.943 (2) Å | 0.50 × 0.13 × 0.13 mm |
Stoe IPDS 2 diffractometer | 2102 independent reflections |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | 1871 reflections with I > 2σ(I) |
Tmin = 0.841, Tmax = 1.000 | Rint = 0.047 |
3715 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | Δρmax = 0.23 e Å−3 |
S = 0.99 | Δρmin = −0.25 e Å−3 |
2102 reflections | Absolute structure: Flack (1983), with 837 Friedel pairs |
152 parameters | Absolute structure parameter: −0.03 (9) |
2 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.56496 (11) | 0.37007 (6) | 0.04622 (3) | 0.0262 (2) | |
O1 | 0.4697 (4) | 0.48208 (15) | −0.18884 (9) | 0.0357 (6) | |
O2 | 0.3843 (4) | 0.69236 (17) | −0.19861 (9) | 0.0348 (6) | |
O3 | 0.4230 (4) | 0.57414 (16) | 0.24408 (8) | 0.0310 (5) | |
N1 | 0.5386 (4) | 0.37186 (18) | 0.20590 (9) | 0.0268 (6) | |
N2 | 0.7453 (4) | 0.54283 (19) | 0.17099 (10) | 0.0247 (6) | |
C1 | 0.5182 (4) | 0.6058 (2) | −0.17793 (10) | 0.0229 (6) | |
C2 | 0.7530 (5) | 0.6264 (3) | −0.13749 (11) | 0.0270 (7) | |
C3 | 0.7105 (5) | 0.5814 (2) | −0.06840 (11) | 0.0245 (7) | |
C4 | 0.9575 (5) | 0.5932 (2) | −0.02951 (10) | 0.0257 (7) | |
C5 | 0.9253 (5) | 0.5770 (2) | 0.04246 (10) | 0.0245 (6) | |
C6 | 0.8745 (4) | 0.4413 (2) | 0.06772 (11) | 0.0215 (6) | |
C7 | 0.8828 (4) | 0.4365 (2) | 0.14098 (11) | 0.0218 (6) | |
C8 | 0.7320 (5) | 0.3151 (2) | 0.16447 (11) | 0.0240 (7) | |
C9 | 0.6168 (5) | 0.2460 (2) | 0.10620 (11) | 0.0290 (8) | |
C10 | 0.5574 (5) | 0.5015 (2) | 0.21013 (10) | 0.0230 (6) | |
H1N | 0.436 (5) | 0.333 (2) | 0.2307 (11) | 0.0320* | |
H1O | 0.33530 | 0.47540 | −0.21090 | 0.0540* | |
H2A | 0.79830 | 0.71980 | −0.13760 | 0.0320* | |
H2B | 0.89920 | 0.57780 | −0.15610 | 0.0320* | |
H2N | 0.803 (5) | 0.6209 (19) | 0.1756 (13) | 0.0300* | |
H3A | 0.57400 | 0.63480 | −0.04840 | 0.0290* | |
H3B | 0.65220 | 0.48990 | −0.06830 | 0.0290* | |
H4A | 1.03430 | 0.67950 | −0.03790 | 0.0310* | |
H4B | 1.08090 | 0.52700 | −0.04490 | 0.0310* | |
H5A | 1.08330 | 0.61010 | 0.06330 | 0.0290* | |
H5B | 0.78140 | 0.63340 | 0.05630 | 0.0290* | |
H6 | 1.01310 | 0.38290 | 0.05110 | 0.0260* | |
H7 | 1.06490 | 0.43340 | 0.15640 | 0.0260* | |
H8 | 0.84720 | 0.25540 | 0.18900 | 0.0290* | |
H9A | 0.45200 | 0.20370 | 0.11760 | 0.0350* | |
H9B | 0.73680 | 0.17900 | 0.09010 | 0.0350* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0226 (3) | 0.0301 (3) | 0.0258 (3) | −0.0050 (2) | −0.0035 (3) | −0.0003 (2) |
O1 | 0.0399 (11) | 0.0238 (9) | 0.0434 (11) | −0.0017 (8) | −0.0178 (9) | 0.0022 (8) |
O2 | 0.0369 (11) | 0.0256 (9) | 0.0420 (11) | 0.0032 (8) | −0.0119 (9) | −0.0002 (8) |
O3 | 0.0361 (10) | 0.0277 (9) | 0.0293 (9) | 0.0008 (8) | 0.0111 (9) | −0.0018 (7) |
N1 | 0.0319 (10) | 0.0225 (10) | 0.0260 (10) | −0.0032 (9) | 0.0074 (9) | 0.0028 (8) |
N2 | 0.0301 (11) | 0.0199 (9) | 0.0241 (10) | −0.0046 (8) | 0.0077 (9) | −0.0031 (8) |
C1 | 0.0242 (12) | 0.0254 (11) | 0.0192 (10) | −0.0011 (9) | 0.0016 (9) | 0.0009 (9) |
C2 | 0.0269 (12) | 0.0299 (12) | 0.0242 (12) | −0.0028 (11) | −0.0001 (10) | 0.0027 (10) |
C3 | 0.0227 (11) | 0.0275 (12) | 0.0234 (12) | 0.0003 (9) | 0.0009 (10) | 0.0007 (10) |
C4 | 0.0258 (11) | 0.0296 (12) | 0.0218 (11) | −0.0048 (10) | −0.0004 (10) | 0.0021 (9) |
C5 | 0.0276 (11) | 0.0259 (11) | 0.0201 (10) | −0.0022 (10) | −0.0043 (12) | −0.0029 (9) |
C6 | 0.0203 (11) | 0.0259 (11) | 0.0182 (10) | 0.0002 (9) | −0.0003 (9) | −0.0004 (9) |
C7 | 0.0190 (11) | 0.0237 (11) | 0.0226 (11) | 0.0006 (9) | −0.0028 (9) | −0.0014 (9) |
C8 | 0.0283 (13) | 0.0209 (11) | 0.0227 (11) | 0.0018 (9) | −0.0012 (10) | 0.0008 (9) |
C9 | 0.0361 (15) | 0.0212 (11) | 0.0296 (13) | −0.0046 (10) | 0.0017 (11) | −0.0032 (10) |
C10 | 0.0257 (11) | 0.0240 (10) | 0.0194 (10) | 0.0004 (10) | −0.0011 (10) | −0.0008 (9) |
S1—C6 | 1.824 (2) | C6—C7 | 1.536 (3) |
S1—C9 | 1.812 (2) | C7—C8 | 1.556 (3) |
O1—C1 | 1.319 (3) | C8—C9 | 1.534 (3) |
O2—C1 | 1.211 (3) | C2—H2A | 0.9900 |
O3—C10 | 1.246 (3) | C2—H2B | 0.9900 |
O1—H1O | 0.8400 | C3—H3A | 0.9900 |
N1—C8 | 1.451 (3) | C3—H3B | 0.9900 |
N1—C10 | 1.342 (3) | C4—H4A | 0.9900 |
N2—C10 | 1.344 (3) | C4—H4B | 0.9900 |
N2—C7 | 1.451 (3) | C5—H5A | 0.9900 |
N1—H1N | 0.85 (2) | C5—H5B | 0.9900 |
N2—H2N | 0.86 (2) | C6—H6 | 1.0000 |
C1—C2 | 1.500 (3) | C7—H7 | 1.0000 |
C2—C3 | 1.535 (3) | C8—H8 | 1.0000 |
C3—C4 | 1.525 (4) | C9—H9A | 0.9900 |
C4—C5 | 1.526 (3) | C9—H9B | 0.9900 |
C5—C6 | 1.518 (3) | ||
C6—S1—C9 | 88.95 (11) | C3—C2—H2B | 109.00 |
C1—O1—H1O | 109.00 | H2A—C2—H2B | 108.00 |
C8—N1—C10 | 112.97 (19) | C2—C3—H3A | 110.00 |
C7—N2—C10 | 112.50 (18) | C2—C3—H3B | 109.00 |
C10—N1—H1N | 118.5 (15) | C4—C3—H3A | 109.00 |
C8—N1—H1N | 127.9 (15) | C4—C3—H3B | 109.00 |
C7—N2—H2N | 125.5 (17) | H3A—C3—H3B | 108.00 |
C10—N2—H2N | 118.6 (18) | C3—C4—H4A | 108.00 |
O1—C1—O2 | 122.7 (2) | C3—C4—H4B | 108.00 |
O2—C1—C2 | 124.4 (2) | C5—C4—H4A | 109.00 |
O1—C1—C2 | 112.9 (2) | C5—C4—H4B | 109.00 |
C1—C2—C3 | 111.9 (2) | H4A—C4—H4B | 107.00 |
C2—C3—C4 | 111.0 (2) | C4—C5—H5A | 108.00 |
C3—C4—C5 | 115.3 (2) | C4—C5—H5B | 108.00 |
C4—C5—C6 | 117.66 (18) | C6—C5—H5A | 108.00 |
S1—C6—C5 | 115.96 (16) | C6—C5—H5B | 108.00 |
C5—C6—C7 | 111.90 (17) | H5A—C5—H5B | 107.00 |
S1—C6—C7 | 104.98 (14) | S1—C6—H6 | 108.00 |
N2—C7—C8 | 102.83 (17) | C5—C6—H6 | 108.00 |
C6—C7—C8 | 109.13 (17) | C7—C6—H6 | 108.00 |
N2—C7—C6 | 113.24 (18) | N2—C7—H7 | 110.00 |
N1—C8—C9 | 113.1 (2) | C6—C7—H7 | 110.00 |
C7—C8—C9 | 108.54 (18) | C8—C7—H7 | 110.00 |
N1—C8—C7 | 102.35 (16) | N1—C8—H8 | 111.00 |
S1—C9—C8 | 106.38 (14) | C7—C8—H8 | 111.00 |
O3—C10—N2 | 124.4 (2) | C9—C8—H8 | 111.00 |
N1—C10—N2 | 109.1 (2) | S1—C9—H9A | 110.00 |
O3—C10—N1 | 126.5 (2) | S1—C9—H9B | 110.00 |
C1—C2—H2A | 109.00 | C8—C9—H9A | 110.00 |
C1—C2—H2B | 109.00 | C8—C9—H9B | 110.00 |
C3—C2—H2A | 109.00 | H9A—C9—H9B | 109.00 |
C9—S1—C6—C5 | −166.31 (17) | C2—C3—C4—C5 | 168.35 (19) |
C9—S1—C6—C7 | −42.28 (15) | C3—C4—C5—C6 | 73.2 (3) |
C6—S1—C9—C8 | 41.21 (17) | C4—C5—C6—S1 | −67.4 (3) |
C10—N1—C8—C7 | −0.8 (2) | C4—C5—C6—C7 | 172.3 (2) |
C10—N1—C8—C9 | −117.4 (2) | S1—C6—C7—N2 | −81.88 (18) |
C8—N1—C10—O3 | −177.1 (2) | S1—C6—C7—C8 | 32.00 (19) |
C8—N1—C10—N2 | 3.5 (3) | C5—C6—C7—N2 | 44.7 (2) |
C10—N2—C7—C6 | 121.9 (2) | C5—C6—C7—C8 | 158.58 (19) |
C10—N2—C7—C8 | 4.3 (2) | N2—C7—C8—N1 | −2.0 (2) |
C7—N2—C10—O3 | 175.6 (2) | N2—C7—C8—C9 | 117.9 (2) |
C7—N2—C10—N1 | −5.0 (3) | C6—C7—C8—N1 | −122.44 (18) |
O1—C1—C2—C3 | −69.4 (3) | C6—C7—C8—C9 | −2.6 (2) |
O2—C1—C2—C3 | 110.4 (3) | N1—C8—C9—S1 | 84.6 (2) |
C1—C2—C3—C4 | 175.51 (19) | C7—C8—C9—S1 | −28.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.85 (2) | 2.24 (2) | 3.044 (3) | 158 (2) |
O1—H1O···O3ii | 0.84 | 1.72 | 2.544 (3) | 167 |
N2—H2N···O2iii | 0.86 (2) | 2.03 (2) | 2.881 (3) | 169 (2) |
C3—H3B···S1 | 0.99 | 2.74 | 3.328 (2) | 119 |
C6—H6···S1iv | 1.00 | 2.87 | 3.689 (2) | 139 |
C8—H8···O1v | 1.00 | 2.53 | 3.340 (3) | 138 |
Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1/2, −y+1, z−1/2; (iii) x+1/2, −y+3/2, −z; (iv) x+1, y, z; (v) x+1/2, −y+1/2, −z. |
[Ag(C10H15N2O3S)]·3H2O | F(000) = 412 |
Mr = 405.22 | Dx = 1.885 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 11662 reflections |
a = 8.7869 (8) Å | θ = 2.1–29.6° |
b = 8.2847 (10) Å | µ = 1.58 mm−1 |
c = 9.8588 (10) Å | T = 173 K |
β = 95.718 (8)° | Plate, colourless |
V = 714.12 (13) Å3 | 0.40 × 0.40 × 0.15 mm |
Z = 2 |
Stoe IPDS 2 diffractometer | 3827 independent reflections |
Radiation source: fine-focus sealed tube | 3718 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 29.2°, θmin = 3.0° |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | h = −12→10 |
Tmin = 0.574, Tmax = 0.810 | k = −11→11 |
8354 measured reflections | l = −13→13 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.0416P)2 + 0.1972P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.061 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.43 e Å−3 |
3827 reflections | Δρmin = −0.52 e Å−3 |
215 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
18 restraints | Extinction coefficient: 0.0228 (16) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1776 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (2) |
[Ag(C10H15N2O3S)]·3H2O | V = 714.12 (13) Å3 |
Mr = 405.22 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.7869 (8) Å | µ = 1.58 mm−1 |
b = 8.2847 (10) Å | T = 173 K |
c = 9.8588 (10) Å | 0.40 × 0.40 × 0.15 mm |
β = 95.718 (8)° |
Stoe IPDS 2 diffractometer | 3827 independent reflections |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | 3718 reflections with I > 2σ(I) |
Tmin = 0.574, Tmax = 0.810 | Rint = 0.024 |
8354 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.061 | Δρmax = 0.43 e Å−3 |
S = 1.07 | Δρmin = −0.52 e Å−3 |
3827 reflections | Absolute structure: Flack (1983), with 1776 Friedel pairs |
215 parameters | Absolute structure parameter: 0.00 (2) |
18 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.95339 (2) | 0.24575 (3) | −0.09734 (2) | 0.0231 (1) | |
S1 | 0.88972 (6) | 0.53872 (7) | −0.04098 (6) | 0.0168 (1) | |
O1A | 0.7544 (5) | 0.1797 (7) | 0.6569 (4) | 0.0355 (11) | 0.600 |
O1B | 0.7674 (10) | 0.1050 (10) | 0.6221 (7) | 0.045 (2) | 0.400 |
O2 | 0.9833 (4) | 0.2655 (4) | 0.6742 (2) | 0.0515 (9) | |
O3 | 0.7373 (2) | 1.0996 (2) | −0.0014 (2) | 0.0277 (6) | |
N1 | 0.6609 (3) | 0.8383 (3) | 0.0354 (3) | 0.0244 (6) | |
N2 | 0.7378 (3) | 0.8979 (3) | −0.1630 (3) | 0.0291 (7) | |
C1 | 0.8718 (4) | 0.2120 (3) | 0.5997 (3) | 0.0319 (9) | |
C2 | 0.8752 (4) | 0.2232 (4) | 0.4474 (3) | 0.0349 (9) | |
C3 | 0.7871 (3) | 0.3698 (4) | 0.3879 (3) | 0.0279 (8) | |
C4 | 0.7933 (3) | 0.3826 (3) | 0.2351 (3) | 0.0251 (7) | |
C5 | 0.7057 (3) | 0.5289 (3) | 0.1744 (3) | 0.0223 (6) | |
C6 | 0.6985 (3) | 0.5401 (3) | 0.0197 (3) | 0.0192 (6) | |
C7 | 0.6224 (3) | 0.6938 (3) | −0.0423 (3) | 0.0208 (6) | |
C8 | 0.6846 (3) | 0.7323 (4) | −0.1818 (2) | 0.0230 (6) | |
C9 | 0.8140 (3) | 0.6155 (3) | −0.2059 (3) | 0.0232 (7) | |
C10 | 0.7136 (3) | 0.9585 (3) | −0.0397 (3) | 0.0225 (7) | |
O1W | 0.5120 (3) | 0.3687 (4) | 0.7272 (3) | 0.0531 (10) | |
O2W | 0.2584 (5) | 0.3155 (6) | 0.5332 (5) | 0.0811 (17) | |
O3W | 0.5032 (6) | 0.5895 (7) | 0.5220 (5) | 0.0921 (19) | |
H2A | 0.83000 | 0.12400 | 0.40430 | 0.0420* | |
H2B | 0.98270 | 0.23030 | 0.42600 | 0.0420* | |
H2N | 0.758 (5) | 0.975 (4) | −0.219 (3) | 0.0350* | |
H3A | 0.67910 | 0.36170 | 0.40760 | 0.0330* | |
H3B | 0.83100 | 0.46880 | 0.43220 | 0.0330* | |
H4A | 0.74940 | 0.28340 | 0.19090 | 0.0300* | |
H4B | 0.90130 | 0.39030 | 0.21550 | 0.0300* | |
H5A | 0.60010 | 0.52520 | 0.20110 | 0.0270* | |
H5B | 0.75470 | 0.62800 | 0.21440 | 0.0270* | |
H6 | 0.64040 | 0.44470 | −0.02010 | 0.0230* | |
H7 | 0.50880 | 0.67970 | −0.05520 | 0.0250* | |
H8 | 0.60060 | 0.72550 | −0.25790 | 0.0280* | |
H9A | 0.89500 | 0.67220 | −0.25020 | 0.0280* | |
H9B | 0.77460 | 0.52570 | −0.26570 | 0.0280* | |
H1N | 0.609 (4) | 0.847 (5) | 0.105 (3) | 0.0290* | |
H1WA | 0.508 (6) | 0.453 (4) | 0.675 (4) | 0.0800* | |
H1WB | 0.563 (6) | 0.293 (5) | 0.691 (5) | 0.0800* | |
H2WA | 0.357 (3) | 0.339 (7) | 0.530 (7) | 0.1220* | |
H2WB | 0.233 (8) | 0.338 (11) | 0.616 (4) | 0.1220* | |
H3WA | 0.449 (6) | 0.675 (6) | 0.499 (6) | 0.1380* | |
H3WB | 0.602 (3) | 0.607 (8) | 0.539 (6) | 0.1380* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0289 (1) | 0.0186 (1) | 0.0214 (1) | 0.0035 (1) | 0.0006 (1) | 0.0022 (1) |
S1 | 0.0182 (2) | 0.0152 (2) | 0.0169 (2) | −0.0010 (2) | 0.0020 (2) | 0.0004 (2) |
O1A | 0.045 (2) | 0.043 (2) | 0.0191 (18) | 0.0015 (19) | 0.0069 (16) | 0.0069 (17) |
O1B | 0.075 (5) | 0.040 (4) | 0.020 (3) | −0.011 (4) | 0.009 (3) | 0.005 (3) |
O2 | 0.0754 (17) | 0.053 (2) | 0.0245 (10) | −0.0103 (16) | −0.0028 (10) | 0.0048 (12) |
O3 | 0.0250 (9) | 0.0191 (9) | 0.0401 (11) | 0.0010 (7) | 0.0095 (8) | −0.0021 (8) |
N1 | 0.0259 (11) | 0.0203 (10) | 0.0285 (11) | 0.0017 (8) | 0.0095 (9) | 0.0021 (9) |
N2 | 0.0446 (14) | 0.0178 (9) | 0.0263 (12) | −0.0023 (9) | 0.0101 (10) | 0.0047 (8) |
C1 | 0.0440 (15) | 0.0313 (18) | 0.0213 (11) | 0.0140 (11) | 0.0083 (11) | 0.0100 (9) |
C2 | 0.0583 (17) | 0.0306 (18) | 0.0162 (10) | 0.0150 (13) | 0.0065 (10) | 0.0035 (10) |
C3 | 0.0366 (14) | 0.0301 (14) | 0.0176 (11) | 0.0031 (11) | 0.0061 (10) | 0.0044 (9) |
C4 | 0.0353 (13) | 0.0215 (11) | 0.0181 (11) | 0.0026 (10) | 0.0006 (10) | 0.0016 (8) |
C5 | 0.0243 (11) | 0.0231 (11) | 0.0198 (11) | −0.0001 (9) | 0.0040 (9) | 0.0028 (9) |
C6 | 0.0175 (10) | 0.0188 (10) | 0.0215 (11) | −0.0028 (9) | 0.0031 (9) | 0.0030 (10) |
C7 | 0.0157 (9) | 0.0193 (10) | 0.0273 (12) | 0.0002 (7) | 0.0012 (9) | 0.0056 (8) |
C8 | 0.0262 (9) | 0.0202 (12) | 0.0217 (9) | −0.0032 (12) | −0.0017 (8) | 0.0051 (11) |
C9 | 0.0309 (12) | 0.0224 (12) | 0.0160 (10) | −0.0002 (9) | 0.0004 (10) | 0.0027 (9) |
C10 | 0.0172 (10) | 0.0193 (11) | 0.0315 (14) | 0.0027 (8) | 0.0047 (10) | 0.0019 (11) |
O1W | 0.0443 (15) | 0.0662 (19) | 0.0505 (16) | −0.0136 (13) | 0.0131 (12) | 0.0137 (14) |
O2W | 0.083 (3) | 0.090 (3) | 0.074 (3) | 0.022 (2) | 0.026 (2) | 0.014 (2) |
O3W | 0.079 (3) | 0.110 (4) | 0.087 (3) | 0.010 (3) | 0.007 (2) | 0.017 (3) |
Ag1—S1 | 2.5642 (7) | N2—H2N | 0.87 (3) |
Ag1—O3i | 2.5148 (18) | C1—C2 | 1.508 (4) |
Ag1—O2ii | 2.299 (2) | C2—C3 | 1.526 (5) |
Ag1—S1iii | 2.5154 (7) | C3—C4 | 1.517 (4) |
Ag1—O1Aii | 2.895 (4) | C4—C5 | 1.526 (4) |
S1—C6 | 1.839 (3) | C5—C6 | 1.523 (4) |
S1—C9 | 1.810 (3) | C6—C7 | 1.537 (4) |
O1A—C1 | 1.253 (6) | C7—C8 | 1.563 (4) |
O1B—C1 | 1.310 (9) | C8—C9 | 1.530 (4) |
O2—C1 | 1.246 (4) | C2—H2A | 0.9900 |
O3—C10 | 1.240 (3) | C2—H2B | 0.9900 |
O1W—H1WB | 0.87 (5) | C3—H3B | 0.9900 |
O1W—H1WA | 0.87 (4) | C3—H3A | 0.9900 |
O2W—H2WA | 0.89 (3) | C4—H4B | 0.9900 |
O2W—H2WB | 0.89 (5) | C4—H4A | 0.9900 |
O3W—H3WB | 0.88 (3) | C5—H5A | 0.9900 |
O3W—H3WA | 0.87 (5) | C5—H5B | 0.9900 |
N1—C10 | 1.350 (4) | C6—H6 | 1.0000 |
N1—C7 | 1.443 (4) | C7—H7 | 1.0000 |
N2—C8 | 1.455 (4) | C8—H8 | 1.0000 |
N2—C10 | 1.352 (4) | C9—H9B | 0.9900 |
N1—H1N | 0.86 (3) | C9—H9A | 0.9900 |
S1—Ag1—O3i | 100.66 (4) | N2—C8—C7 | 102.5 (2) |
S1—Ag1—O2ii | 101.16 (8) | S1—C9—C8 | 107.17 (18) |
S1—Ag1—S1iii | 130.36 (2) | O3—C10—N2 | 126.0 (3) |
O2ii—Ag1—O3i | 124.54 (10) | N1—C10—N2 | 108.2 (2) |
S1iii—Ag1—O3i | 82.03 (4) | O3—C10—N1 | 125.8 (3) |
S1iii—Ag1—O2ii | 118.01 (9) | C1—C2—H2A | 109.00 |
Ag1—S1—C6 | 107.61 (8) | C1—C2—H2B | 109.00 |
Ag1—S1—C9 | 101.93 (9) | C3—C2—H2A | 109.00 |
Ag1—S1—Ag1iv | 130.04 (2) | H2A—C2—H2B | 108.00 |
C6—S1—C9 | 91.38 (13) | C3—C2—H2B | 109.00 |
Ag1iv—S1—C6 | 106.77 (9) | C4—C3—H3A | 109.00 |
Ag1iv—S1—C9 | 112.33 (9) | C4—C3—H3B | 109.00 |
Ag1v—O2—C1 | 113.1 (2) | C2—C3—H3B | 109.00 |
Ag1vi—O3—C10 | 116.72 (17) | C2—C3—H3A | 109.00 |
H1WA—O1W—H1WB | 109 (4) | H3A—C3—H3B | 108.00 |
H2WA—O2W—H2WB | 109 (6) | C3—C4—H4A | 109.00 |
H3WA—O3W—H3WB | 115 (5) | C3—C4—H4B | 109.00 |
C7—N1—C10 | 113.3 (3) | H4A—C4—H4B | 108.00 |
C8—N2—C10 | 112.8 (2) | C5—C4—H4A | 109.00 |
C10—N1—H1N | 128 (3) | C5—C4—H4B | 109.00 |
C7—N1—H1N | 112 (3) | C4—C5—H5A | 109.00 |
C10—N2—H2N | 111 (2) | C4—C5—H5B | 109.00 |
C8—N2—H2N | 134 (2) | C6—C5—H5A | 109.00 |
O2—C1—C2 | 118.2 (3) | C6—C5—H5B | 109.00 |
O1B—C1—C2 | 107.1 (4) | H5A—C5—H5B | 108.00 |
O1A—C1—C2 | 124.1 (3) | C7—C6—H6 | 108.00 |
O1B—C1—O2 | 131.6 (4) | C5—C6—H6 | 108.00 |
O1A—C1—O2 | 116.4 (3) | S1—C6—H6 | 108.00 |
C1—C2—C3 | 111.9 (3) | N1—C7—H7 | 110.00 |
C2—C3—C4 | 111.8 (2) | C6—C7—H7 | 110.00 |
C3—C4—C5 | 112.2 (2) | C8—C7—H7 | 110.00 |
C4—C5—C6 | 114.2 (2) | N2—C8—H8 | 111.00 |
S1—C6—C7 | 104.55 (18) | C7—C8—H8 | 111.00 |
C5—C6—C7 | 115.0 (2) | C9—C8—H8 | 111.00 |
S1—C6—C5 | 112.17 (19) | S1—C9—H9B | 110.00 |
N1—C7—C6 | 114.0 (2) | H9A—C9—H9B | 109.00 |
N1—C7—C8 | 102.4 (2) | C8—C9—H9A | 110.00 |
C6—C7—C8 | 110.1 (2) | C8—C9—H9B | 110.00 |
C7—C8—C9 | 109.8 (2) | S1—C9—H9A | 110.00 |
N2—C8—C9 | 112.5 (2) | ||
O3i—Ag1—S1—C6 | −9.45 (11) | Ag1vi—O3—C10—N2 | −31.5 (4) |
O3i—Ag1—S1—C9 | −104.77 (10) | C10—N1—C7—C6 | 127.4 (3) |
O3i—Ag1—S1—Ag1iv | 122.02 (5) | C10—N1—C7—C8 | 8.6 (3) |
O2ii—Ag1—S1—C6 | 119.25 (13) | C7—N1—C10—O3 | 171.0 (3) |
O2ii—Ag1—S1—C9 | 23.93 (13) | C7—N1—C10—N2 | −9.7 (3) |
O2ii—Ag1—S1—Ag1iv | −109.28 (9) | C10—N2—C8—C7 | −1.2 (3) |
S1iii—Ag1—S1—C6 | −98.00 (10) | C10—N2—C8—C9 | −119.0 (2) |
S1iii—Ag1—S1—C9 | 166.67 (9) | C8—N2—C10—O3 | −174.2 (3) |
S1iii—Ag1—S1—Ag1iv | 33.46 (4) | C8—N2—C10—N1 | 6.5 (3) |
S1—Ag1—O3i—C10i | 163.53 (18) | O1A—C1—C2—C3 | 69.1 (5) |
S1—Ag1—O2ii—C1ii | −103.6 (2) | O2—C1—C2—C3 | −97.5 (4) |
S1—Ag1—S1iii—Ag1iii | 130.05 (3) | C1—C2—C3—C4 | 178.9 (3) |
S1—Ag1—S1iii—C6iii | −98.19 (9) | C2—C3—C4—C5 | −179.9 (2) |
S1—Ag1—S1iii—C9iii | 0.49 (10) | C3—C4—C5—C6 | −175.7 (2) |
Ag1—S1—C6—C5 | 93.70 (17) | C4—C5—C6—S1 | −55.9 (3) |
Ag1—S1—C6—C7 | −141.10 (15) | C4—C5—C6—C7 | −175.2 (2) |
C9—S1—C6—C5 | −163.32 (18) | S1—C6—C7—N1 | −83.7 (2) |
C9—S1—C6—C7 | −38.13 (19) | S1—C6—C7—C8 | 30.7 (2) |
Ag1iv—S1—C6—C5 | −49.48 (18) | C5—C6—C7—N1 | 39.8 (3) |
Ag1iv—S1—C6—C7 | 75.72 (18) | C5—C6—C7—C8 | 154.1 (2) |
Ag1—S1—C9—C8 | 143.67 (16) | N1—C7—C8—N2 | −4.2 (3) |
C6—S1—C9—C8 | 35.35 (19) | N1—C7—C8—C9 | 115.5 (2) |
Ag1iv—S1—C9—C8 | −73.43 (19) | C6—C7—C8—N2 | −125.7 (2) |
Ag1v—O2—C1—O1A | 10.4 (4) | C6—C7—C8—C9 | −6.0 (3) |
Ag1v—O2—C1—C2 | 178.0 (2) | N2—C8—C9—S1 | 91.3 (2) |
Ag1vi—O3—C10—N1 | 147.6 (2) | C7—C8—C9—S1 | −22.1 (3) |
Symmetry codes: (i) x, y−1, z; (ii) x, y, z−1; (iii) −x+2, y−1/2, −z; (iv) −x+2, y+1/2, −z; (v) x, y, z+1; (vi) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1Wvii | 0.86 (3) | 2.06 (3) | 2.925 (4) | 179 (6) |
N2—H2N···O1Aviii | 0.87 (3) | 2.09 (3) | 2.946 (6) | 166 (4) |
O1W—H1WA···O3W | 0.87 (4) | 1.88 (4) | 2.723 (6) | 163 (4) |
O1W—H1WB···O1A | 0.87 (5) | 1.98 (5) | 2.786 (6) | 153 (4) |
O2W—H2WA···O1W | 0.89 (3) | 2.27 (6) | 2.823 (5) | 120 (5) |
O2W—H2WA···O3W | 0.89 (3) | 2.45 (5) | 3.137 (7) | 135 (4) |
O2W—H2WB···O2ix | 0.89 (5) | 2.40 (7) | 2.935 (6) | 119 (6) |
O3W—H3WA···O1Avii | 0.87 (5) | 2.24 (6) | 2.828 (7) | 125 (5) |
O3W—H3WB···O2Wvii | 0.88 (3) | 2.27 (6) | 2.901 (7) | 128 (5) |
C4—H4A···O3i | 0.99 | 2.43 | 3.309 (3) | 148 |
C7—H7···O3x | 1.00 | 2.38 | 3.325 (3) | 157 |
C8—H8···O3Wii | 1.00 | 2.52 | 3.397 (6) | 146 |
Symmetry codes: (i) x, y−1, z; (ii) x, y, z−1; (vii) −x+1, y+1/2, −z+1; (viii) x, y+1, z−1; (ix) x−1, y, z; (x) −x+1, y−1/2, −z. |
[Ag2(NO3)2(C10H16N2O3S)2]·H2O | F(000) = 1704 |
Mr = 846.39 | Dx = 1.922 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 25171 reflections |
a = 21.8568 (12) Å | θ = 1.9–29.6° |
b = 8.0321 (4) Å | µ = 1.56 mm−1 |
c = 16.8886 (9) Å | T = 173 K |
β = 99.337 (4)° | Block, colourless |
V = 2925.6 (3) Å3 | 0.29 × 0.27 × 0.22 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 7861 independent reflections |
Radiation source: fine-focus sealed tube | 7163 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 29.3°, θmin = 1.9° |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | h = −29→29 |
Tmin = 0.878, Tmax = 1.000 | k = −11→10 |
21197 measured reflections | l = −22→23 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.019 | w = 1/[σ2(Fo2) + (0.0254P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.041 | (Δ/σ)max = 0.005 |
S = 0.97 | Δρmax = 0.43 e Å−3 |
7861 reflections | Δρmin = −0.50 e Å−3 |
410 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
7 restraints | Extinction coefficient: 0.00060 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 3655 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.017 (10) |
[Ag2(NO3)2(C10H16N2O3S)2]·H2O | V = 2925.6 (3) Å3 |
Mr = 846.39 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 21.8568 (12) Å | µ = 1.56 mm−1 |
b = 8.0321 (4) Å | T = 173 K |
c = 16.8886 (9) Å | 0.29 × 0.27 × 0.22 mm |
β = 99.337 (4)° |
Stoe IPDS 2 diffractometer | 7861 independent reflections |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | 7163 reflections with I > 2σ(I) |
Tmin = 0.878, Tmax = 1.000 | Rint = 0.024 |
21197 measured reflections |
R[F2 > 2σ(F2)] = 0.019 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.041 | Δρmax = 0.43 e Å−3 |
S = 0.97 | Δρmin = −0.50 e Å−3 |
7861 reflections | Absolute structure: Flack (1983), with 3655 Friedel pairs |
410 parameters | Absolute structure parameter: −0.017 (10) |
7 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.96073 (1) | 0.74638 (2) | 0.73377 (1) | 0.0249 (1) | |
Ag2 | 1.01984 (1) | 1.25094 (2) | 0.76062 (1) | 0.0246 (1) | |
S1 | 1.03829 (2) | 0.96628 (5) | 0.71999 (2) | 0.0173 (1) | |
S2 | 0.93810 (2) | 0.45772 (5) | 0.77023 (3) | 0.0178 (1) | |
O1 | 1.24701 (9) | 0.6217 (2) | 1.18055 (10) | 0.0328 (5) | |
O2 | 1.23609 (9) | 0.8961 (2) | 1.16097 (10) | 0.0349 (5) | |
O3 | 1.05523 (7) | 0.40317 (17) | 0.64498 (8) | 0.0278 (4) | |
O4 | 0.77561 (7) | 0.44477 (17) | 0.31405 (8) | 0.0280 (4) | |
O5 | 0.78634 (9) | 0.17023 (19) | 0.33308 (9) | 0.0305 (5) | |
O6 | 0.93339 (7) | −0.10102 (17) | 0.85394 (8) | 0.0290 (4) | |
O11 | 0.85954 (7) | 0.80387 (18) | 0.65211 (9) | 0.0316 (4) | |
O12 | 0.92529 (6) | 0.7311 (3) | 0.57515 (9) | 0.0399 (5) | |
O13 | 0.82953 (7) | 0.7727 (3) | 0.52437 (9) | 0.0456 (6) | |
O21 | 1.11362 (7) | 1.33413 (19) | 0.84525 (8) | 0.0310 (4) | |
O22 | 1.05366 (6) | 1.2525 (3) | 0.92783 (8) | 0.0385 (4) | |
O23 | 1.13476 (8) | 1.3990 (2) | 0.97149 (9) | 0.0409 (5) | |
N1 | 1.10084 (8) | 0.60691 (19) | 0.73132 (10) | 0.0214 (5) | |
N2 | 1.08333 (9) | 0.6597 (2) | 0.60223 (10) | 0.0237 (5) | |
N3 | 0.90087 (8) | 0.1529 (2) | 0.89484 (10) | 0.0233 (5) | |
N4 | 0.87775 (8) | 0.08728 (19) | 0.76695 (10) | 0.0215 (4) | |
N11 | 0.87129 (7) | 0.7712 (2) | 0.58269 (9) | 0.0245 (5) | |
N21 | 1.10053 (8) | 1.3288 (2) | 0.91605 (10) | 0.0248 (5) | |
C1 | 1.23722 (7) | 0.7492 (4) | 1.13477 (9) | 0.0253 (4) | |
C2 | 1.22782 (10) | 0.7203 (3) | 1.04580 (11) | 0.0295 (6) | |
C3 | 1.17007 (9) | 0.8031 (2) | 1.00042 (11) | 0.0251 (5) | |
C4 | 1.16928 (9) | 0.7957 (2) | 0.91016 (11) | 0.0225 (5) | |
C5 | 1.10729 (9) | 0.8550 (2) | 0.86342 (11) | 0.0210 (5) | |
C6 | 1.11247 (8) | 0.9009 (2) | 0.77740 (11) | 0.0184 (4) | |
C7 | 1.13342 (7) | 0.7636 (3) | 0.72555 (10) | 0.0186 (4) | |
C8 | 1.11426 (9) | 0.8091 (2) | 0.63481 (11) | 0.0214 (5) | |
C9 | 1.07093 (10) | 0.9605 (3) | 0.62781 (12) | 0.0239 (6) | |
C10 | 1.07790 (10) | 0.5436 (2) | 0.65749 (12) | 0.0205 (5) | |
C11 | 0.78917 (10) | 0.3179 (3) | 0.35905 (12) | 0.0224 (5) | |
C12 | 0.80919 (11) | 0.3502 (2) | 0.44667 (12) | 0.0281 (6) | |
C13 | 0.81348 (10) | 0.1982 (2) | 0.49986 (11) | 0.0255 (5) | |
C14 | 0.81140 (8) | 0.2418 (4) | 0.58735 (9) | 0.0257 (4) | |
C15 | 0.87171 (9) | 0.3185 (2) | 0.63114 (10) | 0.0205 (5) | |
C16 | 0.86504 (8) | 0.3778 (2) | 0.71498 (10) | 0.0182 (5) | |
C17 | 0.84567 (7) | 0.2437 (3) | 0.77139 (9) | 0.0195 (4) | |
C18 | 0.86694 (9) | 0.2977 (2) | 0.86060 (11) | 0.0206 (5) | |
C19 | 0.90770 (10) | 0.4545 (3) | 0.86401 (12) | 0.0218 (6) | |
C20 | 0.90639 (10) | 0.0333 (3) | 0.84053 (12) | 0.0212 (5) | |
O1W | 1.00000 | 0.7300 (4) | 1.00000 | 0.0470 (9) | |
O2W | 1.00000 | 0.2348 (5) | 0.50000 | 0.0665 (9) | |
H1N | 1.1099 (12) | 0.541 (3) | 0.7700 (13) | 0.0260* | |
H1O | 1.25930 | 0.65290 | 1.22790 | 0.0490* | |
H2A | 1.22510 | 0.59900 | 1.03550 | 0.0350* | |
H2B | 1.26450 | 0.76270 | 1.02460 | 0.0350* | |
H2N | 1.0720 (11) | 0.648 (3) | 0.5506 (10) | 0.0280* | |
H3A | 1.16880 | 0.92090 | 1.01750 | 0.0300* | |
H3B | 1.13280 | 0.74660 | 1.01370 | 0.0300* | |
H3N | 0.9197 (11) | 0.147 (3) | 0.9438 (11) | 0.0280* | |
H4A | 1.17700 | 0.67980 | 0.89450 | 0.0270* | |
H4B | 1.20300 | 0.86640 | 0.89610 | 0.0270* | |
H4N | 0.8675 (11) | 0.020 (3) | 0.7284 (12) | 0.0260* | |
H4O | 0.76430 | 0.41330 | 0.26650 | 0.0420* | |
H5A | 1.07600 | 0.76570 | 0.86320 | 0.0250* | |
H5B | 1.09290 | 0.95320 | 0.89070 | 0.0250* | |
H6 | 1.14220 | 0.99580 | 0.77880 | 0.0220* | |
H7 | 1.17930 | 0.74690 | 0.73890 | 0.0220* | |
H8 | 1.15160 | 0.83230 | 0.60940 | 0.0260* | |
H9A | 1.03770 | 0.94870 | 0.58080 | 0.0290* | |
H9B | 1.09430 | 1.06390 | 0.62160 | 0.0290* | |
H12A | 0.77960 | 0.42940 | 0.46480 | 0.0340* | |
H12B | 0.85030 | 0.40500 | 0.45410 | 0.0340* | |
H13A | 0.85260 | 0.13870 | 0.49650 | 0.0310* | |
H13B | 0.77870 | 0.12220 | 0.48000 | 0.0310* | |
H14A | 0.80230 | 0.13960 | 0.61600 | 0.0310* | |
H14B | 0.77700 | 0.32120 | 0.58940 | 0.0310* | |
H15A | 0.90530 | 0.23460 | 0.63520 | 0.0250* | |
H15B | 0.88350 | 0.41380 | 0.59960 | 0.0250* | |
H16 | 0.83370 | 0.46940 | 0.70970 | 0.0220* | |
H17 | 0.79980 | 0.22640 | 0.76040 | 0.0230* | |
H18 | 0.83020 | 0.31850 | 0.88760 | 0.0250* | |
H19A | 0.94190 | 0.44900 | 0.91020 | 0.0260* | |
H19B | 0.88280 | 0.55570 | 0.86930 | 0.0260* | |
H1W1 | 0.9851 (16) | 0.793 (4) | 0.9597 (16) | 0.0710* | |
H1W2 | 0.989 (2) | 0.292 (4) | 0.4589 (17) | 0.1000* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0242 (1) | 0.0181 (1) | 0.0311 (1) | −0.0034 (1) | 0.0005 (1) | 0.0018 (1) |
Ag2 | 0.0251 (1) | 0.0182 (1) | 0.0293 (1) | 0.0024 (1) | 0.0004 (1) | −0.0028 (1) |
S1 | 0.0189 (2) | 0.0148 (2) | 0.0174 (2) | 0.0002 (2) | 0.0008 (2) | 0.0011 (2) |
S2 | 0.0197 (2) | 0.0150 (2) | 0.0183 (2) | −0.0009 (2) | 0.0019 (2) | −0.0016 (2) |
O1 | 0.0396 (10) | 0.0333 (8) | 0.0222 (8) | −0.0016 (7) | −0.0051 (7) | −0.0010 (6) |
O2 | 0.0420 (10) | 0.0334 (8) | 0.0253 (8) | 0.0125 (7) | −0.0069 (7) | −0.0045 (7) |
O3 | 0.0414 (8) | 0.0203 (6) | 0.0218 (7) | −0.0045 (6) | 0.0054 (6) | −0.0022 (5) |
O4 | 0.0382 (8) | 0.0253 (7) | 0.0201 (6) | −0.0020 (6) | 0.0035 (6) | 0.0029 (5) |
O5 | 0.0438 (10) | 0.0263 (7) | 0.0190 (7) | 0.0063 (6) | −0.0017 (7) | −0.0031 (6) |
O6 | 0.0426 (9) | 0.0220 (6) | 0.0224 (7) | 0.0043 (6) | 0.0052 (6) | 0.0032 (5) |
O11 | 0.0361 (8) | 0.0360 (8) | 0.0224 (7) | 0.0066 (6) | 0.0042 (6) | −0.0080 (6) |
O12 | 0.0266 (7) | 0.0665 (12) | 0.0263 (6) | 0.0071 (9) | 0.0038 (5) | −0.0042 (9) |
O13 | 0.0329 (7) | 0.0762 (15) | 0.0244 (7) | 0.0086 (9) | −0.0054 (5) | 0.0027 (9) |
O21 | 0.0371 (8) | 0.0371 (8) | 0.0183 (7) | −0.0052 (6) | 0.0032 (6) | 0.0041 (6) |
O22 | 0.0326 (7) | 0.0511 (8) | 0.0323 (7) | −0.0117 (11) | 0.0070 (5) | 0.0008 (10) |
O23 | 0.0459 (10) | 0.0520 (10) | 0.0219 (7) | −0.0142 (8) | −0.0032 (7) | −0.0046 (7) |
N1 | 0.0312 (9) | 0.0167 (7) | 0.0161 (8) | −0.0001 (6) | 0.0037 (6) | 0.0016 (5) |
N2 | 0.0342 (10) | 0.0218 (8) | 0.0154 (7) | −0.0025 (6) | 0.0050 (7) | −0.0010 (6) |
N3 | 0.0311 (9) | 0.0236 (8) | 0.0146 (7) | −0.0005 (6) | 0.0020 (6) | −0.0004 (6) |
N4 | 0.0317 (9) | 0.0169 (7) | 0.0150 (7) | −0.0017 (6) | 0.0015 (6) | −0.0008 (5) |
N11 | 0.0280 (8) | 0.0240 (10) | 0.0206 (7) | 0.0025 (6) | 0.0014 (5) | 0.0002 (6) |
N21 | 0.0294 (9) | 0.0253 (8) | 0.0183 (7) | 0.0023 (6) | −0.0007 (6) | 0.0028 (6) |
C1 | 0.0216 (8) | 0.0320 (8) | 0.0204 (7) | 0.0042 (12) | −0.0025 (5) | 0.0028 (11) |
C2 | 0.0308 (10) | 0.0355 (14) | 0.0203 (8) | 0.0087 (8) | −0.0019 (7) | −0.0018 (8) |
C3 | 0.0264 (10) | 0.0313 (9) | 0.0164 (8) | 0.0049 (7) | −0.0003 (7) | 0.0002 (7) |
C4 | 0.0235 (9) | 0.0257 (9) | 0.0172 (8) | 0.0013 (6) | 0.0000 (6) | 0.0021 (6) |
C5 | 0.0226 (9) | 0.0247 (8) | 0.0150 (8) | 0.0016 (6) | 0.0010 (6) | −0.0001 (6) |
C6 | 0.0173 (8) | 0.0172 (7) | 0.0198 (8) | −0.0002 (6) | 0.0006 (7) | 0.0005 (7) |
C7 | 0.0178 (7) | 0.0193 (9) | 0.0185 (7) | −0.0013 (8) | 0.0025 (5) | 0.0027 (8) |
C8 | 0.0241 (10) | 0.0201 (7) | 0.0213 (9) | 0.0005 (7) | 0.0079 (7) | 0.0022 (7) |
C9 | 0.0318 (11) | 0.0235 (9) | 0.0171 (9) | 0.0000 (8) | 0.0059 (8) | 0.0048 (8) |
C10 | 0.0248 (10) | 0.0209 (8) | 0.0172 (9) | 0.0039 (7) | 0.0074 (7) | 0.0000 (7) |
C11 | 0.0211 (10) | 0.0278 (9) | 0.0188 (9) | −0.0014 (7) | 0.0046 (7) | 0.0008 (8) |
C12 | 0.0405 (12) | 0.0257 (9) | 0.0184 (9) | −0.0093 (8) | 0.0053 (8) | −0.0017 (7) |
C13 | 0.0311 (10) | 0.0243 (9) | 0.0192 (9) | −0.0021 (6) | −0.0020 (7) | −0.0022 (6) |
C14 | 0.0272 (8) | 0.0316 (8) | 0.0167 (7) | −0.0063 (12) | −0.0012 (6) | 0.0005 (11) |
C15 | 0.0230 (9) | 0.0229 (7) | 0.0145 (8) | −0.0020 (7) | −0.0002 (6) | 0.0004 (6) |
C16 | 0.0181 (9) | 0.0181 (8) | 0.0175 (8) | −0.0009 (6) | −0.0002 (6) | −0.0003 (6) |
C17 | 0.0197 (7) | 0.0201 (6) | 0.0190 (7) | −0.0025 (10) | 0.0039 (5) | −0.0023 (10) |
C18 | 0.0254 (9) | 0.0214 (8) | 0.0158 (8) | −0.0024 (6) | 0.0055 (7) | −0.0018 (6) |
C19 | 0.0269 (11) | 0.0220 (9) | 0.0171 (9) | −0.0014 (7) | 0.0056 (7) | −0.0051 (7) |
C20 | 0.0269 (11) | 0.0203 (8) | 0.0168 (9) | −0.0038 (7) | 0.0050 (7) | 0.0008 (7) |
O1W | 0.0495 (14) | 0.0449 (17) | 0.0438 (13) | 0.0000 | −0.0009 (10) | 0.0000 |
O2W | 0.118 (2) | 0.0330 (14) | 0.0347 (12) | 0.0000 | −0.0291 (14) | 0.0000 |
Ag1—S1 | 2.4851 (5) | N4—H4N | 0.85 (2) |
Ag1—S2 | 2.4695 (5) | C1—C2 | 1.501 (2) |
Ag1—O11 | 2.4529 (15) | C2—C3 | 1.520 (3) |
Ag1—O12 | 2.6679 (15) | C3—C4 | 1.523 (3) |
Ag1—O6i | 2.5243 (14) | C4—C5 | 1.529 (3) |
Ag2—S1 | 2.4395 (4) | C5—C6 | 1.521 (3) |
Ag2—S2i | 2.4638 (5) | C6—C7 | 1.524 (3) |
Ag2—O21 | 2.3959 (15) | C7—C8 | 1.565 (3) |
Ag2—O22 | 2.8007 (14) | C8—C9 | 1.534 (3) |
Ag2—O3i | 2.5295 (14) | C11—C12 | 1.496 (3) |
S1—C6 | 1.8261 (18) | C12—C13 | 1.510 (2) |
S1—C9 | 1.815 (2) | C13—C14 | 1.526 (2) |
S2—C16 | 1.8301 (18) | C14—C15 | 1.532 (3) |
S2—C19 | 1.814 (2) | C15—C16 | 1.523 (2) |
O1—C1 | 1.280 (3) | C16—C17 | 1.542 (3) |
O2—C1 | 1.262 (3) | C17—C18 | 1.564 (2) |
O3—C10 | 1.236 (2) | C18—C19 | 1.538 (3) |
O4—C11 | 1.277 (3) | C2—H2B | 0.9900 |
O5—C11 | 1.263 (3) | C2—H2A | 0.9900 |
O6—C20 | 1.233 (3) | C3—H3A | 0.9900 |
O11—N11 | 1.268 (2) | C3—H3B | 0.9900 |
O12—N11 | 1.250 (2) | C4—H4A | 0.9900 |
O13—N11 | 1.230 (2) | C4—H4B | 0.9900 |
O21—N21 | 1.275 (2) | C5—H5A | 0.9900 |
O22—N21 | 1.237 (2) | C5—H5B | 0.9900 |
O23—N21 | 1.236 (2) | C6—H6 | 1.0000 |
O1—H1O | 0.8400 | C7—H7 | 1.0000 |
O4—H4O | 0.8400 | C8—H8 | 1.0000 |
O1W—H1W1ii | 0.87 (3) | C9—H9A | 0.9900 |
O1W—H1W1 | 0.87 (3) | C9—H9B | 0.9900 |
O2W—H1W2iii | 0.84 (3) | C12—H12B | 0.9900 |
O2W—H1W2 | 0.84 (3) | C12—H12A | 0.9900 |
N1—C10 | 1.365 (3) | C13—H13B | 0.9900 |
N1—C7 | 1.457 (3) | C13—H13A | 0.9900 |
N2—C10 | 1.338 (2) | C14—H14A | 0.9900 |
N2—C8 | 1.442 (2) | C14—H14B | 0.9900 |
N3—C18 | 1.448 (2) | C15—H15A | 0.9900 |
N3—C20 | 1.347 (3) | C15—H15B | 0.9900 |
N4—C20 | 1.368 (3) | C16—H16 | 1.0000 |
N4—C17 | 1.447 (3) | C17—H17 | 1.0000 |
N1—H1N | 0.84 (2) | C18—H18 | 1.0000 |
N2—H2N | 0.872 (17) | C19—H19A | 0.9900 |
N3—H3N | 0.863 (19) | C19—H19B | 0.9900 |
S1—Ag1—S2 | 149.08 (2) | S2—C16—C17 | 103.55 (11) |
S1—Ag1—O11 | 112.34 (4) | C15—C16—C17 | 115.67 (14) |
S1—Ag1—O12 | 91.72 (4) | S2—C16—C15 | 112.12 (13) |
S1—Ag1—O6i | 89.10 (3) | N4—C17—C16 | 112.99 (14) |
S2—Ag1—O11 | 96.79 (4) | C16—C17—C18 | 109.44 (16) |
S2—Ag1—O12 | 99.78 (5) | N4—C17—C18 | 102.71 (14) |
S2—Ag1—O6i | 99.92 (3) | C17—C18—C19 | 110.05 (15) |
O11—Ag1—O12 | 49.89 (5) | N3—C18—C17 | 102.40 (15) |
O6i—Ag1—O11 | 92.93 (5) | N3—C18—C19 | 112.74 (17) |
O6i—Ag1—O12 | 139.61 (5) | S2—C19—C18 | 105.72 (14) |
S1—Ag2—O21 | 105.35 (4) | O6—C20—N4 | 125.38 (19) |
S1—Ag2—S2i | 143.62 (2) | O6—C20—N3 | 126.30 (19) |
S1—Ag2—O3i | 98.66 (3) | N3—C20—N4 | 108.31 (19) |
S2i—Ag2—O21 | 109.39 (4) | C1—C2—H2B | 109.00 |
O3i—Ag2—O21 | 89.23 (5) | C1—C2—H2A | 109.00 |
S2i—Ag2—O3i | 92.34 (4) | H2A—C2—H2B | 108.00 |
Ag1—S1—Ag2 | 119.56 (2) | C3—C2—H2A | 109.00 |
Ag1—S1—C6 | 107.84 (6) | C3—C2—H2B | 109.00 |
Ag1—S1—C9 | 115.54 (8) | C4—C3—H3A | 109.00 |
Ag2—S1—C6 | 107.05 (5) | C4—C3—H3B | 109.00 |
Ag2—S1—C9 | 111.79 (8) | H3A—C3—H3B | 108.00 |
C6—S1—C9 | 90.54 (9) | C2—C3—H3B | 109.00 |
Ag1—S2—C16 | 113.31 (6) | C2—C3—H3A | 109.00 |
Ag1—S2—C19 | 110.34 (8) | C3—C4—H4B | 109.00 |
Ag1—S2—Ag2iv | 116.09 (2) | C3—C4—H4A | 109.00 |
C16—S2—C19 | 91.56 (9) | H4A—C4—H4B | 108.00 |
Ag2iv—S2—C16 | 108.18 (6) | C5—C4—H4A | 109.00 |
Ag2iv—S2—C19 | 114.83 (8) | C5—C4—H4B | 109.00 |
Ag2iv—O3—C10 | 118.25 (12) | C6—C5—H5A | 109.00 |
Ag1iv—O6—C20 | 116.48 (12) | C6—C5—H5B | 109.00 |
Ag1—O11—N11 | 100.46 (11) | H5A—C5—H5B | 108.00 |
Ag1—O12—N11 | 90.63 (10) | C4—C5—H5B | 109.00 |
Ag2—O21—N21 | 104.46 (12) | C4—C5—H5A | 109.00 |
C1—O1—H1O | 109.00 | C5—C6—H6 | 108.00 |
C11—O4—H4O | 109.00 | S1—C6—H6 | 108.00 |
H1W1—O1W—H1W1ii | 109 (3) | C7—C6—H6 | 108.00 |
H1W2—O2W—H1W2iii | 113 (3) | C8—C7—H7 | 111.00 |
C7—N1—C10 | 111.83 (15) | C6—C7—H7 | 111.00 |
C8—N2—C10 | 113.76 (16) | N1—C7—H7 | 111.00 |
C18—N3—C20 | 113.42 (16) | N2—C8—H8 | 111.00 |
C17—N4—C20 | 112.48 (16) | C7—C8—H8 | 111.00 |
O11—N11—O12 | 118.95 (15) | C9—C8—H8 | 111.00 |
O11—N11—O13 | 120.23 (16) | S1—C9—H9A | 111.00 |
O12—N11—O13 | 120.77 (16) | C8—C9—H9B | 111.00 |
O21—N21—O23 | 119.67 (17) | H9A—C9—H9B | 109.00 |
O22—N21—O23 | 121.30 (17) | S1—C9—H9B | 111.00 |
O21—N21—O22 | 119.03 (16) | C8—C9—H9A | 110.00 |
C10—N1—H1N | 118.8 (16) | C13—C12—H12A | 108.00 |
C7—N1—H1N | 122.7 (17) | C11—C12—H12A | 108.00 |
C10—N2—H2N | 125.4 (16) | C11—C12—H12B | 108.00 |
C8—N2—H2N | 120.7 (16) | H12A—C12—H12B | 107.00 |
C20—N3—H3N | 122.1 (16) | C13—C12—H12B | 108.00 |
C18—N3—H3N | 124.1 (16) | C14—C13—H13A | 109.00 |
C17—N4—H4N | 121.6 (16) | C14—C13—H13B | 109.00 |
C20—N4—H4N | 121.4 (16) | C12—C13—H13B | 109.00 |
O2—C1—C2 | 119.2 (2) | C12—C13—H13A | 109.00 |
O1—C1—C2 | 117.6 (2) | H13A—C13—H13B | 108.00 |
O1—C1—O2 | 123.17 (16) | C13—C14—H14B | 109.00 |
C1—C2—C3 | 113.88 (18) | C13—C14—H14A | 109.00 |
C2—C3—C4 | 111.19 (16) | H14A—C14—H14B | 108.00 |
C3—C4—C5 | 111.70 (16) | C15—C14—H14A | 109.00 |
C4—C5—C6 | 111.81 (16) | C15—C14—H14B | 109.00 |
S1—C6—C5 | 112.31 (13) | C14—C15—H15A | 109.00 |
S1—C6—C7 | 103.10 (12) | C16—C15—H15B | 109.00 |
C5—C6—C7 | 116.70 (14) | C14—C15—H15B | 109.00 |
N1—C7—C8 | 102.19 (14) | C16—C15—H15A | 109.00 |
N1—C7—C6 | 113.01 (14) | H15A—C15—H15B | 108.00 |
C6—C7—C8 | 109.64 (16) | C17—C16—H16 | 108.00 |
N2—C8—C7 | 102.34 (15) | C15—C16—H16 | 108.00 |
N2—C8—C9 | 112.64 (17) | S2—C16—H16 | 108.00 |
C7—C8—C9 | 108.93 (15) | N4—C17—H17 | 110.00 |
S1—C9—C8 | 106.13 (14) | C16—C17—H17 | 110.00 |
O3—C10—N2 | 126.52 (18) | C18—C17—H17 | 110.00 |
N1—C10—N2 | 108.46 (15) | N3—C18—H18 | 110.00 |
O3—C10—N1 | 125.02 (17) | C19—C18—H18 | 110.00 |
O5—C11—C12 | 119.77 (19) | C17—C18—H18 | 111.00 |
O4—C11—C12 | 116.91 (19) | S2—C19—H19B | 111.00 |
O4—C11—O5 | 123.32 (18) | S2—C19—H19A | 111.00 |
C11—C12—C13 | 115.36 (16) | H19A—C19—H19B | 109.00 |
C12—C13—C14 | 112.44 (17) | C18—C19—H19A | 111.00 |
C13—C14—C15 | 113.65 (15) | C18—C19—H19B | 111.00 |
C14—C15—C16 | 111.70 (15) | ||
S2—Ag1—S1—Ag2 | −139.06 (3) | C19—S2—C16—C15 | −166.52 (13) |
S2—Ag1—S1—C6 | −16.60 (7) | C19—S2—C16—C17 | −41.15 (13) |
S2—Ag1—S1—C9 | 82.88 (9) | Ag2iv—S2—C16—C15 | −49.70 (12) |
O11—Ag1—S1—Ag2 | 61.74 (4) | Ag2iv—S2—C16—C17 | 75.67 (11) |
O11—Ag1—S1—C6 | −175.81 (7) | Ag1—S2—C19—C18 | 152.88 (11) |
O11—Ag1—S1—C9 | −76.33 (9) | C16—S2—C19—C18 | 37.27 (14) |
O12—Ag1—S1—Ag2 | 108.54 (4) | Ag2iv—S2—C19—C18 | −73.62 (14) |
O12—Ag1—S1—C6 | −129.00 (7) | Ag2iv—O3—C10—N1 | 18.5 (3) |
O12—Ag1—S1—C9 | −29.53 (9) | Ag2iv—O3—C10—N2 | −160.31 (18) |
O6i—Ag1—S1—Ag2 | −31.06 (4) | Ag1iv—O6—C20—N3 | −162.71 (17) |
O6i—Ag1—S1—C6 | 91.40 (7) | Ag1iv—O6—C20—N4 | 16.0 (3) |
O6i—Ag1—S1—C9 | −169.13 (9) | Ag1—O11—N11—O12 | −3.0 (2) |
S1—Ag1—S2—C16 | −151.37 (6) | Ag1—O11—N11—O13 | 174.18 (17) |
S1—Ag1—S2—C19 | 107.60 (8) | Ag1—O12—N11—O11 | 2.69 (18) |
S1—Ag1—S2—Ag2iv | −25.27 (4) | Ag1—O12—N11—O13 | −174.44 (18) |
O11—Ag1—S2—C16 | 9.32 (7) | Ag2—O21—N21—O22 | 16.0 (2) |
O11—Ag1—S2—C19 | −91.72 (8) | Ag2—O21—N21—O23 | −164.27 (14) |
O11—Ag1—S2—Ag2iv | 135.42 (4) | C10—N1—C7—C6 | 130.00 (17) |
O12—Ag1—S2—C16 | −41.05 (7) | C10—N1—C7—C8 | 12.3 (2) |
O12—Ag1—S2—C19 | −142.08 (8) | C7—N1—C10—O3 | 170.5 (2) |
O12—Ag1—S2—Ag2iv | 85.05 (4) | C7—N1—C10—N2 | −10.5 (2) |
O6i—Ag1—S2—C16 | 103.51 (7) | C10—N2—C8—C7 | 4.0 (2) |
O6i—Ag1—S2—C19 | 2.48 (8) | C10—N2—C8—C9 | −112.8 (2) |
O6i—Ag1—S2—Ag2iv | −130.39 (4) | C8—N2—C10—O3 | −177.5 (2) |
S1—Ag1—O11—N11 | 73.91 (11) | C8—N2—C10—N1 | 3.6 (2) |
S2—Ag1—O11—N11 | −95.50 (10) | C20—N3—C18—C17 | 4.5 (2) |
O12—Ag1—O11—N11 | 1.59 (11) | C20—N3—C18—C19 | −113.72 (19) |
O6i—Ag1—O11—N11 | 164.14 (11) | C18—N3—C20—O6 | 179.4 (2) |
S1—Ag1—O12—N11 | −119.75 (13) | C18—N3—C20—N4 | 0.5 (2) |
S2—Ag1—O12—N11 | 89.07 (13) | C20—N4—C17—C16 | 126.18 (17) |
O11—Ag1—O12—N11 | −1.59 (11) | C20—N4—C17—C18 | 8.4 (2) |
O6i—Ag1—O12—N11 | −29.12 (18) | C17—N4—C20—O6 | 175.1 (2) |
S1—Ag1—O6i—C20i | 69.14 (15) | C17—N4—C20—N3 | −6.0 (2) |
S2—Ag1—O6i—C20i | −140.60 (15) | O1—C1—C2—C3 | 129.10 (19) |
O11—Ag1—O6i—C20i | −43.18 (16) | O2—C1—C2—C3 | −51.9 (3) |
O12—Ag1—O6i—C20i | −22.45 (19) | C1—C2—C3—C4 | 169.81 (18) |
O21—Ag2—S1—Ag1 | 130.29 (4) | C2—C3—C4—C5 | 171.54 (15) |
O21—Ag2—S1—C6 | 7.45 (7) | C3—C4—C5—C6 | 161.69 (14) |
O21—Ag2—S1—C9 | −90.21 (8) | C4—C5—C6—S1 | 178.36 (11) |
S2i—Ag2—S1—Ag1 | −32.08 (3) | C4—C5—C6—C7 | 59.63 (19) |
S2i—Ag2—S1—C6 | −154.92 (6) | S1—C6—C7—N1 | −76.70 (15) |
S2i—Ag2—S1—C9 | 107.43 (8) | S1—C6—C7—C8 | 36.57 (16) |
O3i—Ag2—S1—Ag1 | −138.12 (4) | C5—C6—C7—N1 | 46.9 (2) |
O3i—Ag2—S1—C6 | 99.03 (7) | C5—C6—C7—C8 | 160.17 (16) |
O3i—Ag2—S1—C9 | 1.38 (8) | N1—C7—C8—N2 | −9.26 (18) |
S1—Ag2—O21—N21 | −104.82 (11) | N1—C7—C8—C9 | 110.19 (17) |
S2i—Ag2—O21—N21 | 64.20 (12) | C6—C7—C8—N2 | −129.37 (16) |
O3i—Ag2—O21—N21 | 156.41 (11) | C6—C7—C8—C9 | −9.9 (2) |
S1—Ag2—S2i—Ag1i | −139.78 (2) | N2—C8—C9—S1 | 91.06 (17) |
S1—Ag2—S2i—C16i | −11.14 (7) | C7—C8—C9—S1 | −21.76 (19) |
S1—Ag2—S2i—C19i | 89.44 (9) | O4—C11—C12—C13 | 169.25 (19) |
O21—Ag2—S2i—Ag1i | 58.26 (4) | O5—C11—C12—C13 | −10.7 (3) |
O21—Ag2—S2i—C16i | −173.10 (7) | C11—C12—C13—C14 | −159.81 (18) |
O21—Ag2—S2i—C19i | −72.52 (9) | C12—C13—C14—C15 | −74.6 (3) |
S1—Ag2—O3i—C10i | −149.71 (15) | C13—C14—C15—C16 | 173.55 (17) |
O21—Ag2—O3i—C10i | −44.30 (15) | C14—C15—C16—S2 | 176.42 (15) |
Ag1—S1—C6—C5 | −52.54 (12) | C14—C15—C16—C17 | 58.0 (2) |
Ag1—S1—C6—C7 | 73.92 (12) | S2—C16—C17—N4 | −80.31 (15) |
Ag2—S1—C6—C5 | 77.32 (11) | S2—C16—C17—C18 | 33.47 (16) |
Ag2—S1—C6—C7 | −156.23 (10) | C15—C16—C17—N4 | 42.8 (2) |
C9—S1—C6—C5 | −169.66 (13) | C15—C16—C17—C18 | 156.53 (15) |
C9—S1—C6—C7 | −43.20 (13) | N4—C17—C18—N3 | −7.32 (18) |
Ag1—S1—C9—C8 | −71.96 (14) | N4—C17—C18—C19 | 112.79 (17) |
Ag2—S1—C9—C8 | 146.79 (11) | C16—C17—C18—N3 | −127.60 (15) |
C6—S1—C9—C8 | 38.16 (14) | C16—C17—C18—C19 | −7.5 (2) |
Ag1—S2—C16—C15 | 80.50 (12) | N3—C18—C19—S2 | 91.22 (16) |
Ag1—S2—C16—C17 | −154.13 (10) | C17—C18—C19—S2 | −22.41 (19) |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, y, −z+2; (iii) −x+2, y, −z+1; (iv) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O6i | 0.87 (3) | 2.13 (3) | 2.980 (2) | 166 (3) |
N1—H1N···O21iv | 0.84 (2) | 2.09 (2) | 2.899 (2) | 163 (2) |
O1—H1O···O5v | 0.84 | 1.78 | 2.609 (2) | 167 |
O2W—H1W2···O3iii | 0.84 (3) | 2.06 (3) | 2.885 (2) | 168 (4) |
N2—H2N···O12iii | 0.87 (2) | 2.24 (2) | 3.026 (2) | 151 (2) |
N3—H3N···O22vi | 0.86 (2) | 2.31 (2) | 3.103 (2) | 152 (2) |
N4—H4N···O11iv | 0.85 (2) | 2.15 (2) | 2.975 (2) | 164 (2) |
O4—H4O···O2vii | 0.84 | 1.79 | 2.619 (2) | 167 |
C2—H2B···O23viii | 0.99 | 2.45 | 3.384 (3) | 157 |
C8—H8···O13iii | 1.00 | 2.41 | 3.145 (2) | 130 |
Symmetry codes: (i) x, y+1, z; (iii) −x+2, y, −z+1; (iv) x, y−1, z; (v) x+1/2, y+1/2, z+1; (vi) −x+2, y−1, −z+2; (vii) x−1/2, y−1/2, z−1; (viii) −x+5/2, y−1/2, −z+2. |
[Ag(C10H16N2O3S)2](PF6) | F(000) = 2256 |
Mr = 741.46 | Dx = 1.776 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 45970 reflections |
a = 15.1130 (7) Å | θ = 1.4–26.1° |
b = 9.6028 (3) Å | µ = 1.02 mm−1 |
c = 28.6670 (13) Å | T = 173 K |
β = 90.946 (4)° | Rod, colourless |
V = 4159.8 (3) Å3 | 0.37 × 0.25 × 0.24 mm |
Z = 6 |
Stoe IPDS 2 diffractometer | 14703 independent reflections |
Radiation source: fine-focus sealed tube | 13212 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ and ω rotation scans | θmax = 25.6°, θmin = 1.4° |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | h = −18→18 |
Tmin = 0.718, Tmax = 0.818 | k = −11→11 |
43114 measured reflections | l = −34→34 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0556P)2 + 7.6945P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.011 |
14703 reflections | Δρmax = 1.54 e Å−3 |
1123 parameters | Δρmin = −0.76 e Å−3 |
13 restraints | Absolute structure: Flack (1983), with 6357 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (2) |
[Ag(C10H16N2O3S)2](PF6) | V = 4159.8 (3) Å3 |
Mr = 741.46 | Z = 6 |
Monoclinic, P21 | Mo Kα radiation |
a = 15.1130 (7) Å | µ = 1.02 mm−1 |
b = 9.6028 (3) Å | T = 173 K |
c = 28.6670 (13) Å | 0.37 × 0.25 × 0.24 mm |
β = 90.946 (4)° |
Stoe IPDS 2 diffractometer | 14703 independent reflections |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | 13212 reflections with I > 2σ(I) |
Tmin = 0.718, Tmax = 0.818 | Rint = 0.038 |
43114 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.109 | Δρmax = 1.54 e Å−3 |
S = 1.04 | Δρmin = −0.76 e Å−3 |
14703 reflections | Absolute structure: Flack (1983), with 6357 Friedel pairs |
1123 parameters | Absolute structure parameter: 0.02 (2) |
13 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.74254 (3) | 0.04295 (5) | 0.53499 (2) | 0.0356 (1) | |
Ag2 | 0.74467 (3) | −0.01916 (4) | 0.20739 (2) | 0.0309 (1) | |
Ag3 | 0.76187 (3) | −0.03889 (4) | 0.87207 (2) | 0.0343 (1) | |
S1 | 0.89717 (10) | 0.09861 (17) | 0.52393 (5) | 0.0351 (5) | |
S2 | 0.59194 (10) | 0.00347 (17) | 0.50466 (6) | 0.0382 (5) | |
S3 | 0.90071 (9) | 0.04039 (17) | 0.19347 (5) | 0.0304 (4) | |
S4 | 0.59740 (11) | −0.06943 (17) | 0.17364 (6) | 0.0401 (5) | |
S5 | 0.91685 (10) | 0.02224 (16) | 0.85439 (6) | 0.0351 (5) | |
S6 | 0.60741 (10) | −0.09365 (16) | 0.85650 (5) | 0.0323 (4) | |
O1 | 0.8150 (3) | −0.1144 (5) | 0.28093 (15) | 0.0404 (16) | |
O2 | 0.9272 (3) | −0.2639 (5) | 0.27644 (17) | 0.0448 (17) | |
O3 | 0.6383 (3) | 0.3785 (5) | 0.53016 (15) | 0.0366 (14) | |
O4 | 0.6419 (4) | 0.0353 (6) | 0.27792 (19) | 0.0650 (19) | |
O5 | 0.5509 (3) | 0.2158 (6) | 0.2754 (2) | 0.0571 (19) | |
O6 | 0.8433 (3) | −0.2954 (5) | 0.51144 (16) | 0.0437 (17) | |
O7 | 0.8274 (3) | −0.1289 (5) | −0.05355 (15) | 0.0444 (16) | |
O8 | 0.9405 (3) | −0.2736 (5) | −0.06018 (16) | 0.0437 (17) | |
O9 | 0.6371 (3) | 0.3109 (5) | 0.20200 (17) | 0.0369 (14) | |
O10 | 0.6535 (3) | 0.0566 (6) | −0.04810 (17) | 0.0553 (17) | |
O11 | 0.5633 (3) | 0.2270 (6) | −0.06839 (18) | 0.0562 (19) | |
O12 | 0.8550 (3) | −0.3552 (5) | 0.19640 (15) | 0.0374 (14) | |
O13 | 0.9269 (3) | −0.2415 (6) | 0.58958 (17) | 0.0473 (17) | |
O14 | 0.8116 (4) | −0.1125 (6) | 0.60760 (18) | 0.063 (2) | |
O15 | 0.6519 (3) | 0.2917 (5) | 0.85867 (17) | 0.0426 (17) | |
O16 | 0.6562 (4) | 0.1006 (6) | 0.60682 (17) | 0.0591 (19) | |
O17 | 0.5784 (3) | 0.2957 (6) | 0.61117 (17) | 0.0522 (17) | |
O18 | 0.8659 (3) | −0.3683 (5) | 0.86200 (15) | 0.0360 (14) | |
N1 | 0.7653 (4) | 0.3686 (6) | 0.48719 (18) | 0.0350 (17) | |
N2 | 0.7770 (4) | 0.3591 (7) | 0.56336 (19) | 0.0467 (19) | |
N3 | 0.7210 (4) | −0.2707 (7) | 0.4632 (2) | 0.0440 (17) | |
N4 | 0.7010 (4) | −0.2714 (7) | 0.5391 (2) | 0.046 (2) | |
N5 | 0.7675 (3) | 0.3137 (5) | 0.16132 (18) | 0.0299 (17) | |
N6 | 0.7756 (4) | 0.2819 (6) | 0.23654 (18) | 0.0370 (17) | |
N7 | 0.7433 (4) | −0.3306 (5) | 0.14290 (18) | 0.0344 (17) | |
N8 | 0.7077 (4) | −0.3371 (7) | 0.2159 (2) | 0.045 (2) | |
N9 | 0.7852 (4) | 0.3106 (5) | 0.82275 (19) | 0.0363 (17) | |
N10 | 0.7852 (4) | 0.2507 (6) | 0.89572 (19) | 0.0400 (17) | |
N11 | 0.7410 (4) | −0.3408 (5) | 0.81676 (17) | 0.0320 (17) | |
N12 | 0.7256 (4) | −0.3764 (6) | 0.89140 (18) | 0.0387 (17) | |
C1 | 0.8795 (4) | −0.1671 (6) | 0.2981 (2) | 0.0319 (17) | |
C2 | 0.9172 (4) | −0.1309 (7) | 0.3451 (2) | 0.0371 (19) | |
C3 | 0.8775 (4) | 0.0027 (6) | 0.3652 (2) | 0.037 (2) | |
C4 | 0.9068 (4) | 0.0377 (7) | 0.4138 (2) | 0.0351 (17) | |
C5 | 0.8665 (4) | 0.1735 (6) | 0.4313 (2) | 0.0316 (17) | |
C6 | 0.9031 (4) | 0.2251 (7) | 0.4758 (2) | 0.0319 (17) | |
C7 | 0.8597 (4) | 0.3599 (7) | 0.4953 (2) | 0.0356 (19) | |
C8 | 0.8685 (4) | 0.3638 (8) | 0.5485 (2) | 0.039 (2) | |
C9 | 0.9203 (4) | 0.2367 (8) | 0.5659 (2) | 0.044 (3) | |
C10 | 0.7188 (4) | 0.3699 (6) | 0.5270 (2) | 0.0293 (17) | |
C11 | 0.5766 (4) | 0.0926 (7) | 0.2908 (2) | 0.039 (2) | |
C12 | 0.5168 (4) | 0.0347 (8) | 0.3279 (2) | 0.043 (2) | |
C13 | 0.5234 (5) | 0.1128 (8) | 0.3737 (2) | 0.046 (2) | |
C14 | 0.6146 (5) | 0.1078 (7) | 0.3968 (2) | 0.045 (2) | |
C15 | 0.6457 (4) | −0.0402 (8) | 0.4131 (2) | 0.0407 (19) | |
C16 | 0.5934 (4) | −0.1034 (7) | 0.4509 (2) | 0.0401 (19) | |
C17 | 0.6255 (5) | −0.2509 (7) | 0.4672 (2) | 0.046 (2) | |
C18 | 0.6114 (4) | −0.2661 (8) | 0.5203 (3) | 0.044 (2) | |
C19 | 0.5575 (4) | −0.1468 (7) | 0.5380 (3) | 0.045 (2) | |
C20 | 0.7621 (5) | −0.2808 (7) | 0.5051 (2) | 0.041 (2) | |
C21 | 0.8941 (4) | −0.1808 (6) | −0.0373 (2) | 0.0286 (17) | |
C22 | 0.9296 (4) | −0.1500 (7) | 0.0106 (2) | 0.0367 (17) | |
C23 | 0.8899 (4) | −0.0205 (8) | 0.0317 (2) | 0.0380 (17) | |
C24 | 0.9143 (4) | 0.0010 (6) | 0.0824 (2) | 0.0309 (19) | |
C25 | 0.8732 (4) | 0.1321 (6) | 0.1022 (2) | 0.0310 (17) | |
C26 | 0.9071 (4) | 0.1774 (6) | 0.1489 (2) | 0.0297 (17) | |
C27 | 0.8618 (4) | 0.3064 (6) | 0.1695 (2) | 0.0316 (17) | |
C28 | 0.8677 (4) | 0.2973 (7) | 0.2240 (2) | 0.037 (2) | |
C29 | 0.9227 (4) | 0.1717 (7) | 0.2378 (2) | 0.039 (2) | |
C30 | 0.7178 (5) | 0.3043 (6) | 0.1997 (2) | 0.0299 (19) | |
C31 | 0.5896 (4) | 0.1262 (8) | −0.0405 (2) | 0.042 (2) | |
C32 | 0.5332 (5) | 0.1182 (9) | 0.0012 (2) | 0.053 (3) | |
C33 | 0.5548 (5) | −0.0017 (8) | 0.0339 (3) | 0.053 (3) | |
C34 | 0.6367 (4) | 0.0227 (7) | 0.0636 (2) | 0.040 (2) | |
C35 | 0.6731 (5) | −0.1076 (8) | 0.0858 (2) | 0.046 (2) | |
C36 | 0.6146 (5) | −0.1778 (8) | 0.1212 (3) | 0.045 (2) | |
C37 | 0.6478 (5) | −0.3197 (7) | 0.1396 (3) | 0.045 (2) | |
C38 | 0.6208 (5) | −0.3384 (8) | 0.1913 (3) | 0.045 (3) | |
C39 | 0.5629 (5) | −0.2203 (8) | 0.2052 (3) | 0.050 (3) | |
C40 | 0.7753 (4) | −0.3409 (6) | 0.1859 (2) | 0.0313 (19) | |
C41 | 0.8835 (4) | −0.1578 (7) | 0.6174 (2) | 0.0353 (19) | |
C42 | 0.9311 (5) | −0.1299 (7) | 0.6628 (2) | 0.042 (2) | |
C43 | 0.8810 (5) | −0.0284 (9) | 0.6925 (2) | 0.048 (2) | |
C44 | 0.9204 (4) | −0.0047 (7) | 0.7412 (2) | 0.0361 (19) | |
C45 | 0.8767 (4) | 0.1175 (7) | 0.7649 (2) | 0.038 (2) | |
C46 | 0.9187 (4) | 0.1600 (7) | 0.8099 (2) | 0.0353 (17) | |
C47 | 0.8776 (4) | 0.2922 (6) | 0.8334 (2) | 0.0346 (19) | |
C48 | 0.8784 (4) | 0.2751 (7) | 0.8866 (2) | 0.037 (2) | |
C49 | 0.9365 (4) | 0.1503 (7) | 0.9003 (2) | 0.042 (2) | |
C50 | 0.7335 (4) | 0.2855 (6) | 0.8588 (2) | 0.0306 (19) | |
C51 | 0.6085 (4) | 0.1757 (8) | 0.6277 (2) | 0.0390 (19) | |
C52 | 0.5738 (5) | 0.1462 (8) | 0.6755 (2) | 0.045 (2) | |
C53 | 0.6161 (5) | 0.0164 (8) | 0.6962 (2) | 0.048 (3) | |
C54 | 0.5883 (4) | −0.0151 (8) | 0.7449 (2) | 0.0376 (17) | |
C55 | 0.6343 (4) | −0.1494 (7) | 0.7618 (2) | 0.0350 (17) | |
C56 | 0.5989 (4) | −0.2097 (6) | 0.8068 (2) | 0.0314 (17) | |
C57 | 0.6455 (4) | −0.3466 (6) | 0.8218 (2) | 0.0331 (17) | |
C58 | 0.6329 (4) | −0.3655 (7) | 0.8746 (2) | 0.0373 (19) | |
C59 | 0.5846 (5) | −0.2396 (7) | 0.8948 (2) | 0.041 (2) | |
C60 | 0.7850 (4) | −0.3623 (6) | 0.8575 (2) | 0.0316 (19) | |
P1 | 0.21129 (14) | 0.9947 (2) | 0.30814 (6) | 0.0467 (6) | |
F1 | 0.2866 (4) | 0.9512 (8) | 0.27213 (18) | 0.101 (3) | |
F2 | 0.1402 (4) | 0.9519 (6) | 0.26921 (17) | 0.084 (2) | |
F3 | 0.2087 (4) | 1.1455 (5) | 0.28668 (19) | 0.082 (2) | |
F4 | 0.2816 (4) | 1.0320 (9) | 0.34590 (18) | 0.107 (3) | |
F5 | 0.1356 (4) | 1.0324 (5) | 0.34279 (17) | 0.0753 (19) | |
F6 | 0.2128 (5) | 0.8401 (5) | 0.32875 (18) | 0.093 (2) | |
P2 | 0.76099 (15) | 0.4588 (2) | 0.02081 (6) | 0.0484 (6) | |
F7 | 0.7278 (8) | 0.6043 (8) | 0.0358 (2) | 0.171 (5) | |
F8 | 0.6842 (4) | 0.4388 (9) | −0.01645 (19) | 0.109 (3) | |
F9 | 0.8188 (4) | 0.5277 (7) | −0.01773 (19) | 0.098 (3) | |
F10 | 0.7968 (6) | 0.3138 (7) | 0.0045 (2) | 0.115 (3) | |
F11 | 0.8378 (5) | 0.4728 (9) | 0.05782 (18) | 0.118 (3) | |
F12 | 0.7069 (5) | 0.3853 (9) | 0.0596 (2) | 0.118 (3) | |
P3 | 0.72542 (17) | 0.50489 (17) | 0.35078 (6) | 0.0529 (7) | |
F13 | 0.7082 (7) | 0.6615 (5) | 0.36258 (19) | 0.137 (4) | |
F14 | 0.6493 (4) | 0.4982 (9) | 0.31409 (19) | 0.118 (3) | |
F15 | 0.7904 (5) | 0.5487 (6) | 0.31071 (17) | 0.091 (2) | |
F16 | 0.7490 (5) | 0.3478 (5) | 0.33947 (16) | 0.084 (2) | |
F17 | 0.8043 (5) | 0.5076 (8) | 0.38776 (19) | 0.110 (3) | |
F18 | 0.6638 (5) | 0.4581 (8) | 0.39175 (19) | 0.109 (3) | |
H1N | 0.749 (4) | 0.400 (8) | 0.4597 (13) | 0.0420* | |
H2A | 0.90620 | −0.20890 | 0.36680 | 0.0440* | |
H2B | 0.98200 | −0.11920 | 0.34270 | 0.0440* | |
H2N | 0.755 (5) | 0.367 (9) | 0.5921 (13) | 0.0560* | |
H2O | 0.90030 | −0.28950 | 0.25200 | 0.0670* | |
H3A | 0.89280 | 0.08140 | 0.34450 | 0.0440* | |
H3B | 0.81220 | −0.00640 | 0.36460 | 0.0440* | |
H3N | 0.748 (4) | −0.288 (9) | 0.4369 (15) | 0.0530* | |
H4A | 0.97210 | 0.04570 | 0.41480 | 0.0420* | |
H4B | 0.88990 | −0.03910 | 0.43490 | 0.0420* | |
H4N | 0.714 (5) | −0.270 (9) | 0.5689 (9) | 0.0560* | |
H5A | 0.87480 | 0.24610 | 0.40730 | 0.0380* | |
H5B | 0.80210 | 0.15960 | 0.43470 | 0.0380* | |
H5N | 0.740 (4) | 0.333 (7) | 0.1348 (13) | 0.0360* | |
H5O | 0.58730 | 0.24530 | 0.25580 | 0.0710* | |
H6 | 0.96710 | 0.24600 | 0.47090 | 0.0380* | |
H6N | 0.762 (5) | 0.273 (8) | 0.2663 (10) | 0.0440* | |
H7 | 0.88910 | 0.44360 | 0.48180 | 0.0430* | |
H7N | 0.765 (4) | −0.346 (8) | 0.1156 (12) | 0.0410* | |
H8 | 0.89780 | 0.45190 | 0.55910 | 0.0470* | |
H8N | 0.706 (5) | −0.370 (8) | 0.2445 (13) | 0.0540* | |
H8O | 0.90870 | −0.30900 | −0.08140 | 0.0660* | |
H9A | 0.90080 | 0.20920 | 0.59730 | 0.0530* | |
H9B | 0.98450 | 0.25720 | 0.56730 | 0.0530* | |
H9N | 0.760 (4) | 0.307 (8) | 0.7948 (13) | 0.0440* | |
H10N | 0.776 (5) | 0.253 (8) | 0.9259 (9) | 0.0480* | |
H11N | 0.776 (4) | −0.345 (7) | 0.7934 (16) | 0.0390* | |
H11O | 0.59710 | 0.23170 | −0.09130 | 0.0840* | |
H12A | 0.45480 | 0.03820 | 0.31620 | 0.0510* | |
H12B | 0.53210 | −0.06420 | 0.33340 | 0.0510* | |
H12N | 0.726 (4) | −0.448 (5) | 0.910 (2) | 0.0470* | |
H13A | 0.47990 | 0.07330 | 0.39550 | 0.0550* | |
H13B | 0.50720 | 0.21140 | 0.36810 | 0.0550* | |
H13O | 0.89420 | −0.26380 | 0.56680 | 0.0710* | |
H14A | 0.61480 | 0.17040 | 0.42430 | 0.0540* | |
H14B | 0.65820 | 0.14480 | 0.37460 | 0.0540* | |
H15A | 0.64360 | −0.10350 | 0.38580 | 0.0490* | |
H15B | 0.70820 | −0.03390 | 0.42380 | 0.0490* | |
H16 | 0.53100 | −0.11270 | 0.43930 | 0.0480* | |
H17 | 0.59260 | −0.32540 | 0.44970 | 0.0540* | |
H17O | 0.59900 | 0.30950 | 0.58450 | 0.0780* | |
H18 | 0.58040 | −0.35590 | 0.52680 | 0.0520* | |
H19A | 0.56910 | −0.13200 | 0.57170 | 0.0540* | |
H19B | 0.49350 | −0.16480 | 0.53310 | 0.0540* | |
H22A | 0.99460 | −0.13850 | 0.00910 | 0.0440* | |
H22B | 0.91760 | −0.23050 | 0.03110 | 0.0440* | |
H23A | 0.82470 | −0.02590 | 0.02860 | 0.0460* | |
H23B | 0.90970 | 0.06160 | 0.01380 | 0.0460* | |
H24A | 0.89420 | −0.08040 | 0.10060 | 0.0370* | |
H24B | 0.97940 | 0.00700 | 0.08580 | 0.0370* | |
H25A | 0.88260 | 0.20900 | 0.07980 | 0.0370* | |
H25B | 0.80850 | 0.11720 | 0.10420 | 0.0370* | |
H26 | 0.97110 | 0.20100 | 0.14540 | 0.0350* | |
H27 | 0.89100 | 0.39340 | 0.15840 | 0.0380* | |
H28 | 0.89340 | 0.38450 | 0.23760 | 0.0450* | |
H29A | 0.90560 | 0.13720 | 0.26890 | 0.0470* | |
H29B | 0.98640 | 0.19590 | 0.23880 | 0.0470* | |
H32A | 0.47070 | 0.10960 | −0.00930 | 0.0630* | |
H32B | 0.53890 | 0.20650 | 0.01880 | 0.0630* | |
H33A | 0.50390 | −0.01730 | 0.05460 | 0.0640* | |
H33B | 0.56310 | −0.08730 | 0.01530 | 0.0640* | |
H34A | 0.68290 | 0.06490 | 0.04410 | 0.0480* | |
H34B | 0.62250 | 0.09020 | 0.08850 | 0.0480* | |
H35A | 0.73030 | −0.08450 | 0.10120 | 0.0560* | |
H35B | 0.68550 | −0.17540 | 0.06070 | 0.0560* | |
H36 | 0.55540 | −0.19330 | 0.10600 | 0.0540* | |
H37 | 0.62300 | −0.39710 | 0.12000 | 0.0540* | |
H38 | 0.59010 | −0.42950 | 0.19580 | 0.0540* | |
H39A | 0.56860 | −0.20350 | 0.23920 | 0.0600* | |
H39B | 0.50030 | −0.24200 | 0.19760 | 0.0600* | |
H42A | 0.99060 | −0.09190 | 0.65650 | 0.0510* | |
H42B | 0.93890 | −0.21860 | 0.68010 | 0.0510* | |
H43A | 0.81960 | −0.06250 | 0.69570 | 0.0580* | |
H43B | 0.87810 | 0.06220 | 0.67610 | 0.0580* | |
H44A | 0.91240 | −0.08960 | 0.76030 | 0.0440* | |
H44B | 0.98470 | 0.01310 | 0.73890 | 0.0440* | |
H45A | 0.87730 | 0.19810 | 0.74340 | 0.0460* | |
H45B | 0.81410 | 0.09350 | 0.77060 | 0.0460* | |
H46 | 0.98210 | 0.18150 | 0.80360 | 0.0420* | |
H47 | 0.91150 | 0.37740 | 0.82450 | 0.0410* | |
H48 | 0.89970 | 0.36200 | 0.90240 | 0.0440* | |
H49A | 0.91920 | 0.11270 | 0.93100 | 0.0500* | |
H49B | 0.99970 | 0.17730 | 0.90180 | 0.0500* | |
H52A | 0.50880 | 0.13360 | 0.67360 | 0.0530* | |
H52B | 0.58640 | 0.22670 | 0.69620 | 0.0530* | |
H53A | 0.60080 | −0.06410 | 0.67610 | 0.0580* | |
H53B | 0.68120 | 0.02760 | 0.69600 | 0.0580* | |
H54A | 0.52330 | −0.02700 | 0.74570 | 0.0450* | |
H54B | 0.60470 | 0.06330 | 0.76580 | 0.0450* | |
H55A | 0.62830 | −0.22060 | 0.73700 | 0.0420* | |
H55B | 0.69820 | −0.13000 | 0.76630 | 0.0420* | |
H56 | 0.53480 | −0.23120 | 0.80140 | 0.0380* | |
H57 | 0.62020 | −0.42760 | 0.80420 | 0.0400* | |
H58 | 0.59980 | −0.45340 | 0.88110 | 0.0450* | |
H59A | 0.60650 | −0.21980 | 0.92690 | 0.0490* | |
H59B | 0.52010 | −0.25760 | 0.89590 | 0.0490* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0343 (2) | 0.0354 (3) | 0.0373 (2) | −0.0072 (2) | 0.0051 (2) | −0.0044 (2) |
Ag2 | 0.0354 (2) | 0.0220 (2) | 0.0352 (2) | −0.0068 (2) | 0.0000 (2) | 0.0002 (2) |
Ag3 | 0.0384 (2) | 0.0249 (2) | 0.0394 (2) | −0.0069 (2) | −0.0058 (2) | 0.0029 (2) |
S1 | 0.0297 (8) | 0.0427 (9) | 0.0327 (8) | −0.0020 (7) | −0.0032 (6) | 0.0015 (6) |
S2 | 0.0334 (7) | 0.0371 (10) | 0.0443 (9) | −0.0028 (6) | 0.0064 (6) | −0.0029 (6) |
S3 | 0.0352 (7) | 0.0263 (7) | 0.0296 (7) | −0.0029 (7) | −0.0011 (5) | 0.0030 (6) |
S4 | 0.0340 (8) | 0.0298 (9) | 0.0567 (10) | −0.0020 (6) | 0.0038 (7) | −0.0029 (7) |
S5 | 0.0361 (8) | 0.0281 (8) | 0.0411 (8) | −0.0013 (6) | −0.0022 (6) | 0.0048 (6) |
S6 | 0.0348 (8) | 0.0278 (7) | 0.0343 (8) | 0.0010 (6) | 0.0048 (6) | −0.0030 (6) |
O1 | 0.048 (3) | 0.039 (3) | 0.034 (2) | 0.013 (2) | −0.008 (2) | 0.0026 (19) |
O2 | 0.042 (3) | 0.043 (3) | 0.049 (3) | 0.011 (2) | −0.007 (2) | −0.018 (2) |
O3 | 0.031 (2) | 0.042 (3) | 0.037 (2) | 0.0003 (19) | 0.0033 (18) | 0.0061 (19) |
O4 | 0.070 (3) | 0.062 (4) | 0.064 (3) | 0.033 (3) | 0.033 (3) | 0.021 (3) |
O5 | 0.046 (3) | 0.056 (3) | 0.070 (4) | 0.015 (3) | 0.024 (3) | 0.024 (3) |
O6 | 0.043 (3) | 0.043 (3) | 0.045 (3) | 0.008 (2) | 0.000 (2) | −0.014 (2) |
O7 | 0.054 (3) | 0.043 (3) | 0.036 (2) | 0.016 (2) | −0.007 (2) | −0.004 (2) |
O8 | 0.040 (3) | 0.050 (3) | 0.041 (3) | 0.014 (2) | −0.005 (2) | −0.021 (2) |
O9 | 0.027 (2) | 0.030 (2) | 0.054 (3) | −0.0042 (18) | 0.006 (2) | 0.000 (2) |
O10 | 0.063 (3) | 0.055 (3) | 0.048 (3) | 0.027 (3) | 0.007 (2) | 0.009 (3) |
O11 | 0.048 (3) | 0.069 (4) | 0.052 (3) | 0.025 (3) | 0.014 (2) | 0.023 (3) |
O12 | 0.043 (3) | 0.035 (2) | 0.034 (2) | 0.005 (2) | −0.003 (2) | −0.0091 (19) |
O13 | 0.045 (3) | 0.054 (3) | 0.043 (3) | 0.013 (2) | 0.008 (2) | −0.009 (2) |
O14 | 0.070 (4) | 0.076 (4) | 0.043 (3) | 0.043 (3) | −0.007 (3) | −0.015 (3) |
O15 | 0.039 (3) | 0.039 (3) | 0.050 (3) | 0.007 (2) | 0.004 (2) | 0.012 (2) |
O16 | 0.088 (4) | 0.051 (3) | 0.039 (3) | 0.029 (3) | 0.024 (3) | 0.006 (2) |
O17 | 0.054 (3) | 0.060 (3) | 0.043 (3) | 0.030 (3) | 0.017 (2) | 0.016 (2) |
O18 | 0.035 (3) | 0.035 (2) | 0.038 (2) | 0.0033 (19) | −0.0010 (19) | −0.0092 (19) |
N1 | 0.041 (3) | 0.036 (3) | 0.028 (3) | −0.003 (2) | 0.005 (2) | 0.002 (2) |
N2 | 0.040 (3) | 0.071 (4) | 0.029 (3) | 0.001 (3) | −0.005 (2) | −0.011 (3) |
N3 | 0.047 (3) | 0.043 (3) | 0.042 (3) | 0.005 (3) | 0.000 (3) | −0.007 (3) |
N4 | 0.045 (4) | 0.062 (4) | 0.032 (3) | 0.007 (3) | 0.001 (3) | −0.002 (3) |
N5 | 0.035 (3) | 0.026 (3) | 0.029 (3) | 0.006 (2) | 0.006 (2) | 0.001 (2) |
N6 | 0.038 (3) | 0.045 (3) | 0.028 (3) | −0.004 (3) | 0.005 (2) | −0.003 (2) |
N7 | 0.045 (3) | 0.023 (3) | 0.035 (3) | 0.005 (2) | −0.001 (2) | −0.002 (2) |
N8 | 0.054 (4) | 0.050 (4) | 0.031 (3) | −0.004 (3) | 0.000 (3) | 0.000 (3) |
N9 | 0.049 (3) | 0.026 (3) | 0.034 (3) | 0.003 (2) | 0.006 (2) | 0.001 (2) |
N10 | 0.044 (3) | 0.047 (3) | 0.029 (3) | −0.003 (3) | 0.000 (2) | 0.000 (2) |
N11 | 0.041 (3) | 0.030 (3) | 0.025 (3) | 0.011 (2) | 0.002 (2) | −0.005 (2) |
N12 | 0.044 (3) | 0.044 (3) | 0.028 (3) | −0.007 (3) | 0.000 (2) | 0.004 (2) |
C1 | 0.036 (3) | 0.025 (3) | 0.035 (3) | −0.001 (3) | 0.009 (3) | −0.002 (2) |
C2 | 0.032 (3) | 0.038 (4) | 0.041 (3) | 0.006 (3) | −0.004 (3) | −0.002 (3) |
C3 | 0.052 (4) | 0.029 (4) | 0.029 (3) | 0.005 (3) | −0.002 (3) | −0.005 (2) |
C4 | 0.033 (3) | 0.037 (3) | 0.035 (3) | 0.000 (3) | −0.005 (2) | 0.005 (3) |
C5 | 0.028 (3) | 0.032 (3) | 0.035 (3) | 0.000 (2) | 0.004 (2) | 0.003 (2) |
C6 | 0.029 (3) | 0.033 (3) | 0.034 (3) | −0.004 (3) | 0.006 (2) | 0.004 (3) |
C7 | 0.030 (3) | 0.035 (3) | 0.042 (4) | −0.004 (3) | 0.011 (3) | −0.007 (3) |
C8 | 0.031 (3) | 0.046 (4) | 0.041 (4) | −0.003 (3) | −0.001 (3) | −0.014 (3) |
C9 | 0.035 (4) | 0.059 (5) | 0.038 (4) | −0.013 (3) | −0.007 (3) | −0.001 (3) |
C10 | 0.032 (3) | 0.023 (3) | 0.033 (3) | 0.000 (2) | 0.004 (3) | 0.000 (2) |
C11 | 0.045 (4) | 0.044 (4) | 0.029 (3) | 0.004 (3) | −0.009 (3) | 0.005 (3) |
C12 | 0.052 (4) | 0.048 (4) | 0.028 (3) | −0.002 (3) | 0.005 (3) | −0.001 (3) |
C13 | 0.056 (4) | 0.043 (4) | 0.040 (4) | 0.002 (3) | 0.010 (3) | 0.000 (3) |
C14 | 0.054 (4) | 0.038 (4) | 0.043 (4) | −0.001 (3) | 0.009 (3) | −0.001 (3) |
C15 | 0.036 (3) | 0.044 (4) | 0.042 (3) | −0.002 (3) | 0.000 (3) | 0.001 (3) |
C16 | 0.035 (3) | 0.031 (3) | 0.054 (4) | −0.006 (3) | −0.010 (3) | −0.003 (3) |
C17 | 0.051 (4) | 0.034 (4) | 0.051 (4) | −0.013 (3) | −0.014 (3) | −0.006 (3) |
C18 | 0.027 (3) | 0.048 (4) | 0.056 (4) | −0.011 (3) | 0.000 (3) | 0.009 (3) |
C19 | 0.035 (4) | 0.039 (4) | 0.060 (4) | −0.007 (3) | 0.005 (3) | 0.009 (3) |
C20 | 0.046 (4) | 0.033 (4) | 0.045 (4) | −0.002 (3) | 0.010 (3) | −0.012 (3) |
C21 | 0.030 (3) | 0.023 (3) | 0.033 (3) | 0.003 (2) | 0.004 (2) | −0.006 (2) |
C22 | 0.035 (3) | 0.036 (3) | 0.039 (3) | 0.010 (3) | −0.003 (3) | −0.007 (3) |
C23 | 0.042 (3) | 0.036 (3) | 0.036 (3) | 0.012 (3) | 0.005 (2) | 0.000 (3) |
C24 | 0.034 (3) | 0.029 (4) | 0.030 (3) | 0.000 (2) | 0.007 (2) | −0.001 (2) |
C25 | 0.030 (3) | 0.028 (3) | 0.035 (3) | −0.001 (2) | 0.002 (2) | 0.001 (2) |
C26 | 0.029 (3) | 0.027 (3) | 0.033 (3) | 0.000 (2) | 0.002 (2) | 0.001 (2) |
C27 | 0.035 (3) | 0.022 (3) | 0.038 (3) | −0.007 (2) | 0.010 (3) | −0.004 (2) |
C28 | 0.042 (4) | 0.031 (3) | 0.039 (4) | −0.012 (3) | 0.006 (3) | −0.014 (3) |
C29 | 0.041 (4) | 0.042 (4) | 0.033 (3) | −0.011 (3) | −0.005 (3) | −0.005 (3) |
C30 | 0.044 (4) | 0.016 (3) | 0.030 (3) | −0.005 (3) | 0.010 (3) | 0.001 (2) |
C31 | 0.033 (3) | 0.060 (5) | 0.034 (3) | 0.004 (3) | −0.005 (3) | 0.004 (3) |
C32 | 0.046 (4) | 0.071 (5) | 0.042 (4) | 0.010 (4) | 0.004 (3) | 0.015 (4) |
C33 | 0.053 (4) | 0.056 (5) | 0.051 (4) | −0.012 (4) | 0.001 (3) | 0.015 (3) |
C34 | 0.037 (3) | 0.035 (4) | 0.047 (4) | 0.005 (3) | 0.001 (3) | −0.004 (3) |
C35 | 0.051 (4) | 0.048 (4) | 0.040 (4) | 0.000 (3) | −0.006 (3) | −0.005 (3) |
C36 | 0.034 (3) | 0.045 (4) | 0.056 (4) | 0.001 (3) | −0.010 (3) | −0.011 (3) |
C37 | 0.049 (4) | 0.027 (3) | 0.059 (4) | −0.003 (3) | −0.011 (3) | −0.009 (3) |
C38 | 0.037 (4) | 0.033 (4) | 0.065 (5) | −0.007 (3) | −0.007 (3) | 0.014 (3) |
C39 | 0.035 (4) | 0.042 (4) | 0.073 (5) | −0.017 (3) | 0.006 (3) | 0.013 (4) |
C40 | 0.049 (4) | 0.014 (3) | 0.031 (3) | −0.003 (3) | 0.007 (3) | −0.008 (2) |
C41 | 0.043 (4) | 0.033 (3) | 0.030 (3) | 0.007 (3) | 0.008 (3) | −0.004 (3) |
C42 | 0.046 (4) | 0.041 (4) | 0.040 (4) | 0.016 (3) | 0.004 (3) | −0.001 (3) |
C43 | 0.059 (4) | 0.051 (4) | 0.035 (3) | 0.027 (4) | 0.002 (3) | −0.003 (3) |
C44 | 0.035 (3) | 0.026 (3) | 0.047 (4) | 0.000 (3) | −0.004 (3) | 0.006 (3) |
C45 | 0.040 (4) | 0.037 (4) | 0.038 (3) | 0.007 (3) | 0.008 (3) | 0.001 (3) |
C46 | 0.034 (3) | 0.032 (3) | 0.040 (3) | −0.005 (3) | 0.004 (3) | 0.008 (3) |
C47 | 0.036 (3) | 0.023 (3) | 0.045 (4) | −0.002 (3) | 0.006 (3) | −0.005 (3) |
C48 | 0.036 (4) | 0.024 (3) | 0.051 (4) | −0.009 (3) | −0.001 (3) | −0.004 (3) |
C49 | 0.039 (4) | 0.042 (4) | 0.043 (4) | −0.009 (3) | −0.014 (3) | 0.000 (3) |
C50 | 0.043 (4) | 0.021 (3) | 0.028 (3) | 0.002 (3) | 0.003 (3) | 0.003 (2) |
C51 | 0.034 (3) | 0.046 (4) | 0.037 (3) | 0.007 (3) | −0.002 (3) | −0.001 (3) |
C52 | 0.044 (4) | 0.051 (4) | 0.039 (4) | 0.016 (3) | 0.008 (3) | 0.006 (3) |
C53 | 0.052 (4) | 0.048 (5) | 0.044 (4) | 0.022 (3) | 0.008 (3) | 0.015 (3) |
C54 | 0.034 (3) | 0.036 (3) | 0.043 (3) | 0.011 (3) | 0.004 (2) | 0.009 (3) |
C55 | 0.031 (3) | 0.039 (3) | 0.035 (3) | 0.007 (3) | 0.000 (3) | 0.005 (3) |
C56 | 0.033 (3) | 0.030 (3) | 0.031 (3) | −0.002 (3) | −0.003 (2) | 0.003 (2) |
C57 | 0.034 (3) | 0.026 (3) | 0.039 (3) | −0.002 (2) | −0.007 (3) | −0.004 (2) |
C58 | 0.035 (3) | 0.029 (3) | 0.048 (4) | −0.005 (3) | 0.005 (3) | 0.002 (3) |
C59 | 0.041 (4) | 0.040 (4) | 0.041 (4) | −0.005 (3) | 0.014 (3) | 0.002 (3) |
C60 | 0.039 (4) | 0.020 (3) | 0.036 (3) | 0.002 (2) | 0.005 (3) | −0.005 (2) |
P1 | 0.0713 (12) | 0.0390 (11) | 0.0302 (8) | 0.0005 (9) | 0.0102 (8) | 0.0038 (7) |
F1 | 0.112 (4) | 0.131 (6) | 0.060 (3) | 0.051 (5) | 0.033 (3) | 0.025 (4) |
F2 | 0.115 (4) | 0.079 (4) | 0.058 (3) | −0.008 (4) | −0.018 (3) | −0.011 (3) |
F3 | 0.134 (5) | 0.041 (3) | 0.072 (3) | −0.009 (3) | 0.034 (3) | 0.012 (2) |
F4 | 0.095 (4) | 0.171 (8) | 0.056 (3) | −0.039 (5) | −0.004 (3) | 0.000 (4) |
F5 | 0.105 (4) | 0.057 (3) | 0.065 (3) | 0.005 (3) | 0.036 (3) | 0.005 (2) |
F6 | 0.178 (6) | 0.045 (3) | 0.055 (3) | 0.022 (3) | 0.014 (3) | 0.019 (2) |
P2 | 0.0826 (13) | 0.0342 (10) | 0.0284 (8) | 0.0061 (10) | −0.0014 (8) | 0.0006 (8) |
F7 | 0.360 (14) | 0.070 (4) | 0.082 (4) | 0.112 (7) | 0.015 (6) | −0.002 (3) |
F8 | 0.091 (4) | 0.178 (8) | 0.057 (3) | 0.001 (5) | −0.011 (3) | 0.015 (4) |
F9 | 0.124 (5) | 0.107 (5) | 0.063 (3) | −0.046 (4) | −0.010 (3) | 0.028 (3) |
F10 | 0.219 (8) | 0.067 (4) | 0.059 (3) | 0.046 (5) | 0.004 (4) | −0.018 (3) |
F11 | 0.143 (5) | 0.157 (6) | 0.053 (3) | −0.056 (5) | −0.045 (3) | 0.024 (4) |
F12 | 0.142 (6) | 0.160 (7) | 0.054 (3) | −0.028 (5) | 0.029 (4) | 0.029 (4) |
P3 | 0.1054 (16) | 0.0251 (10) | 0.0284 (8) | −0.0049 (9) | 0.0061 (9) | −0.0006 (6) |
F13 | 0.326 (12) | 0.032 (3) | 0.055 (3) | 0.034 (5) | 0.028 (5) | −0.008 (2) |
F14 | 0.110 (4) | 0.182 (8) | 0.061 (3) | 0.021 (5) | −0.012 (3) | −0.037 (4) |
F15 | 0.161 (5) | 0.062 (3) | 0.050 (3) | −0.023 (4) | 0.029 (3) | 0.001 (3) |
F16 | 0.179 (6) | 0.030 (2) | 0.044 (2) | −0.002 (3) | 0.018 (3) | −0.0042 (19) |
F17 | 0.144 (5) | 0.134 (7) | 0.050 (3) | −0.018 (5) | −0.016 (3) | −0.003 (3) |
F18 | 0.157 (6) | 0.105 (5) | 0.065 (3) | −0.037 (5) | 0.046 (4) | −0.008 (4) |
Ag1—S1 | 2.4232 (16) | C15—C16 | 1.482 (9) |
Ag1—S2 | 2.4524 (16) | C16—C17 | 1.566 (9) |
Ag1—O16 | 2.518 (5) | C17—C18 | 1.547 (10) |
Ag1—O14 | 2.753 (5) | C18—C19 | 1.499 (10) |
Ag2—S3 | 2.4655 (15) | C21—C22 | 1.496 (8) |
Ag2—S4 | 2.4600 (17) | C22—C23 | 1.511 (10) |
Ag2—O1 | 2.517 (4) | C23—C24 | 1.508 (8) |
Ag2—O4 | 2.623 (6) | C24—C25 | 1.518 (8) |
Ag3—S5 | 2.4752 (16) | C25—C26 | 1.490 (8) |
Ag3—S6 | 2.4270 (16) | C26—C27 | 1.538 (8) |
Ag3—O7i | 2.491 (4) | C27—C28 | 1.566 (8) |
Ag3—O10i | 2.981 (5) | C28—C29 | 1.514 (9) |
S1—C6 | 1.842 (6) | C31—C32 | 1.482 (9) |
S1—C9 | 1.821 (7) | C32—C33 | 1.517 (11) |
S2—C16 | 1.852 (6) | C33—C34 | 1.509 (10) |
S2—C19 | 1.812 (7) | C34—C35 | 1.504 (10) |
S3—C26 | 1.838 (6) | C35—C36 | 1.515 (11) |
S3—C29 | 1.817 (6) | C36—C37 | 1.542 (11) |
S4—C36 | 1.850 (8) | C37—C38 | 1.554 (12) |
S4—C39 | 1.790 (8) | C38—C39 | 1.491 (11) |
S5—C46 | 1.838 (6) | C41—C42 | 1.501 (9) |
S5—C49 | 1.822 (6) | C42—C43 | 1.507 (10) |
S6—C56 | 1.812 (6) | C43—C44 | 1.526 (8) |
S6—C59 | 1.817 (7) | C44—C45 | 1.513 (9) |
P1—F5 | 1.570 (6) | C45—C46 | 1.486 (8) |
P1—F6 | 1.598 (5) | C46—C47 | 1.570 (9) |
P1—F4 | 1.546 (6) | C47—C48 | 1.534 (8) |
P1—F1 | 1.605 (6) | C48—C49 | 1.533 (9) |
P1—F2 | 1.590 (6) | C51—C52 | 1.502 (8) |
P1—F3 | 1.574 (5) | C52—C53 | 1.517 (10) |
P2—F8 | 1.576 (6) | C53—C54 | 1.496 (8) |
P2—F9 | 1.566 (6) | C54—C55 | 1.540 (10) |
P2—F10 | 1.568 (7) | C55—C56 | 1.519 (8) |
P2—F7 | 1.548 (8) | C56—C57 | 1.549 (8) |
P2—F11 | 1.565 (7) | C57—C58 | 1.539 (8) |
P2—F12 | 1.560 (7) | C58—C59 | 1.531 (9) |
P3—F17 | 1.582 (7) | C2—H2A | 0.9900 |
P3—F15 | 1.581 (7) | C2—H2B | 0.9900 |
P3—F16 | 1.585 (5) | C3—H3A | 0.9900 |
P3—F13 | 1.564 (5) | C3—H3B | 0.9900 |
P3—F14 | 1.547 (6) | C4—H4A | 0.9900 |
P3—F18 | 1.576 (7) | C4—H4B | 0.9900 |
O1—C1 | 1.197 (7) | C5—H5A | 0.9900 |
O2—C1 | 1.336 (8) | C5—H5B | 0.9900 |
O3—C10 | 1.224 (8) | C6—H6 | 1.0000 |
O4—C11 | 1.194 (9) | C7—H7 | 1.0000 |
O5—C11 | 1.319 (9) | C8—H8 | 1.0000 |
O6—C20 | 1.246 (9) | C9—H9A | 0.9900 |
O7—C21 | 1.211 (7) | C9—H9B | 0.9900 |
O8—C21 | 1.316 (7) | C12—H12A | 0.9900 |
O9—C30 | 1.224 (9) | C12—H12B | 0.9900 |
O10—C31 | 1.197 (8) | C13—H13B | 0.9900 |
O11—C31 | 1.313 (9) | C13—H13A | 0.9900 |
O12—C40 | 1.244 (8) | C14—H14B | 0.9900 |
O13—C41 | 1.315 (8) | C14—H14A | 0.9900 |
O14—C41 | 1.200 (9) | C15—H15A | 0.9900 |
O15—C50 | 1.235 (8) | C15—H15B | 0.9900 |
O16—C51 | 1.188 (9) | C16—H16 | 1.0000 |
O17—C51 | 1.324 (9) | C17—H17 | 1.0000 |
O18—C60 | 1.229 (8) | C18—H18 | 1.0000 |
O2—H2O | 0.8400 | C19—H19B | 0.9900 |
O5—H5O | 0.8400 | C19—H19A | 0.9900 |
O8—H8O | 0.8400 | C22—H22A | 0.9900 |
O11—H11O | 0.8400 | C22—H22B | 0.9900 |
O13—H13O | 0.8400 | C23—H23A | 0.9900 |
O17—H17O | 0.8400 | C23—H23B | 0.9900 |
N1—C7 | 1.444 (9) | C24—H24B | 0.9900 |
N1—C10 | 1.350 (8) | C24—H24A | 0.9900 |
N2—C8 | 1.454 (8) | C25—H25B | 0.9900 |
N2—C10 | 1.357 (8) | C25—H25A | 0.9900 |
N3—C17 | 1.462 (10) | C26—H26 | 1.0000 |
N3—C20 | 1.347 (8) | C27—H27 | 1.0000 |
N4—C20 | 1.357 (9) | C28—H28 | 1.0000 |
N4—C18 | 1.450 (9) | C29—H29A | 0.9900 |
N5—C27 | 1.442 (8) | C29—H29B | 0.9900 |
N5—C30 | 1.345 (8) | C32—H32A | 0.9900 |
N6—C30 | 1.376 (9) | C32—H32B | 0.9900 |
N6—C28 | 1.451 (9) | C33—H33B | 0.9900 |
N7—C37 | 1.449 (10) | C33—H33A | 0.9900 |
N7—C40 | 1.320 (8) | C34—H34A | 0.9900 |
N8—C40 | 1.347 (8) | C34—H34B | 0.9900 |
N8—C38 | 1.480 (10) | C35—H35A | 0.9900 |
N9—C50 | 1.328 (8) | C35—H35B | 0.9900 |
N9—C47 | 1.435 (9) | C36—H36 | 1.0000 |
N10—C48 | 1.456 (9) | C37—H37 | 1.0000 |
N10—C50 | 1.347 (8) | C38—H38 | 1.0000 |
N11—C60 | 1.350 (8) | C39—H39B | 0.9900 |
N11—C57 | 1.454 (9) | C39—H39A | 0.9900 |
N12—C58 | 1.478 (8) | C42—H42A | 0.9900 |
N12—C60 | 1.341 (8) | C42—H42B | 0.9900 |
N1—H1N | 0.88 (5) | C43—H43A | 0.9900 |
N2—H2N | 0.90 (5) | C43—H43B | 0.9900 |
N3—H3N | 0.88 (5) | C44—H44B | 0.9900 |
N4—H4N | 0.87 (3) | C44—H44A | 0.9900 |
N5—H5N | 0.88 (4) | C45—H45A | 0.9900 |
N6—H6N | 0.89 (3) | C45—H45B | 0.9900 |
N7—H7N | 0.87 (4) | C46—H46 | 1.0000 |
N8—H8N | 0.88 (4) | C47—H47 | 1.0000 |
N9—H9N | 0.88 (4) | C48—H48 | 1.0000 |
N10—H10N | 0.88 (3) | C49—H49A | 0.9900 |
N11—H11N | 0.86 (5) | C49—H49B | 0.9900 |
N12—H12N | 0.87 (5) | C52—H52A | 0.9900 |
C1—C2 | 1.495 (8) | C52—H52B | 0.9900 |
C2—C3 | 1.533 (9) | C53—H53A | 0.9900 |
C3—C4 | 1.493 (8) | C53—H53B | 0.9900 |
C4—C5 | 1.528 (9) | C54—H54A | 0.9900 |
C5—C6 | 1.468 (8) | C54—H54B | 0.9900 |
C6—C7 | 1.559 (9) | C55—H55A | 0.9900 |
C7—C8 | 1.529 (8) | C55—H55B | 0.9900 |
C8—C9 | 1.529 (10) | C56—H56 | 1.0000 |
C11—C12 | 1.513 (9) | C57—H57 | 1.0000 |
C12—C13 | 1.514 (9) | C58—H58 | 1.0000 |
C13—C14 | 1.520 (10) | C59—H59A | 0.9900 |
C14—C15 | 1.566 (10) | C59—H59B | 0.9900 |
S1—Ag1—S2 | 151.54 (6) | O16—C51—C52 | 124.7 (7) |
S1—Ag1—O16 | 124.92 (14) | C51—C52—C53 | 111.1 (6) |
S2—Ag1—O16 | 80.41 (14) | C52—C53—C54 | 114.1 (6) |
S3—Ag2—S4 | 147.51 (6) | C53—C54—C55 | 109.3 (5) |
S3—Ag2—O1 | 80.10 (11) | C54—C55—C56 | 115.0 (5) |
S3—Ag2—O4 | 131.20 (13) | S6—C56—C57 | 106.1 (4) |
S4—Ag2—O1 | 128.67 (11) | C55—C56—C57 | 113.2 (5) |
S4—Ag2—O4 | 78.40 (13) | S6—C56—C55 | 114.3 (4) |
O1—Ag2—O4 | 70.97 (16) | C56—C57—C58 | 108.1 (5) |
S5—Ag3—S6 | 157.56 (6) | N11—C57—C58 | 104.0 (5) |
S5—Ag3—O7i | 83.88 (11) | N11—C57—C56 | 112.8 (5) |
S6—Ag3—O7i | 116.73 (11) | C57—C58—C59 | 110.3 (5) |
Ag1—S1—C6 | 107.6 (2) | N12—C58—C59 | 112.8 (5) |
Ag1—S1—C9 | 104.4 (2) | N12—C58—C57 | 101.4 (5) |
C6—S1—C9 | 90.2 (3) | S6—C59—C58 | 106.5 (4) |
Ag1—S2—C16 | 110.9 (2) | O18—C60—N12 | 126.6 (6) |
Ag1—S2—C19 | 102.1 (2) | N11—C60—N12 | 108.4 (5) |
C16—S2—C19 | 90.3 (3) | O18—C60—N11 | 125.0 (6) |
Ag2—S3—C26 | 109.9 (2) | C1—C2—H2B | 109.00 |
Ag2—S3—C29 | 102.3 (2) | C1—C2—H2A | 109.00 |
C26—S3—C29 | 88.8 (3) | H2A—C2—H2B | 108.00 |
Ag2—S4—C36 | 107.0 (2) | C3—C2—H2A | 109.00 |
Ag2—S4—C39 | 103.3 (3) | C3—C2—H2B | 109.00 |
C36—S4—C39 | 90.1 (4) | C2—C3—H3A | 108.00 |
Ag3—S5—C46 | 109.8 (2) | C4—C3—H3B | 108.00 |
Ag3—S5—C49 | 99.0 (2) | C2—C3—H3B | 108.00 |
C46—S5—C49 | 90.7 (3) | C4—C3—H3A | 109.00 |
Ag3—S6—C56 | 109.5 (2) | H3A—C3—H3B | 107.00 |
Ag3—S6—C59 | 104.3 (2) | C5—C4—H4B | 109.00 |
C56—S6—C59 | 89.4 (3) | C3—C4—H4A | 109.00 |
F4—P1—F5 | 90.2 (3) | C3—C4—H4B | 109.00 |
F4—P1—F6 | 87.2 (4) | C5—C4—H4A | 109.00 |
F5—P1—F6 | 89.2 (3) | H4A—C4—H4B | 108.00 |
F1—P1—F6 | 89.4 (4) | H5A—C5—H5B | 107.00 |
F2—P1—F3 | 87.2 (3) | C4—C5—H5B | 108.00 |
F2—P1—F4 | 178.3 (4) | C6—C5—H5B | 108.00 |
F1—P1—F2 | 87.7 (3) | C4—C5—H5A | 109.00 |
F1—P1—F3 | 90.1 (3) | C6—C5—H5A | 108.00 |
F1—P1—F4 | 91.4 (3) | S1—C6—H6 | 107.00 |
F1—P1—F5 | 177.9 (3) | C5—C6—H6 | 107.00 |
F3—P1—F6 | 178.6 (3) | C7—C6—H6 | 107.00 |
F2—P1—F6 | 91.4 (3) | N1—C7—H7 | 110.00 |
F3—P1—F4 | 94.2 (4) | C8—C7—H7 | 110.00 |
F2—P1—F5 | 90.7 (3) | C6—C7—H7 | 110.00 |
F3—P1—F5 | 91.2 (3) | C9—C8—H8 | 111.00 |
F7—P2—F9 | 90.1 (4) | N2—C8—H8 | 111.00 |
F7—P2—F10 | 178.1 (5) | C7—C8—H8 | 111.00 |
F7—P2—F8 | 93.4 (5) | S1—C9—H9A | 111.00 |
F8—P2—F11 | 177.9 (5) | C8—C9—H9A | 111.00 |
F8—P2—F12 | 92.3 (4) | C8—C9—H9B | 111.00 |
F9—P2—F10 | 88.0 (4) | S1—C9—H9B | 110.00 |
F7—P2—F11 | 88.5 (5) | H9A—C9—H9B | 109.00 |
F7—P2—F12 | 92.0 (4) | C11—C12—H12B | 109.00 |
F8—P2—F9 | 89.2 (3) | C13—C12—H12A | 109.00 |
F8—P2—F10 | 86.8 (4) | C11—C12—H12A | 109.00 |
F11—P2—F12 | 87.0 (4) | H12A—C12—H12B | 108.00 |
F9—P2—F12 | 177.4 (4) | C13—C12—H12B | 109.00 |
F10—P2—F11 | 91.3 (4) | C12—C13—H13A | 109.00 |
F9—P2—F11 | 91.5 (3) | H13A—C13—H13B | 108.00 |
F10—P2—F12 | 89.9 (4) | C14—C13—H13B | 109.00 |
F13—P3—F15 | 90.5 (4) | C12—C13—H13B | 109.00 |
F13—P3—F16 | 176.6 (5) | C14—C13—H13A | 109.00 |
F13—P3—F14 | 93.6 (5) | C13—C14—H14A | 109.00 |
F17—P3—F18 | 87.3 (4) | C13—C14—H14B | 108.00 |
F14—P3—F17 | 178.4 (4) | C15—C14—H14A | 108.00 |
F14—P3—F18 | 93.0 (4) | C15—C14—H14B | 109.00 |
F15—P3—F16 | 87.7 (3) | H14A—C14—H14B | 107.00 |
F13—P3—F17 | 88.0 (4) | C14—C15—H15B | 108.00 |
F13—P3—F18 | 90.6 (4) | C16—C15—H15A | 108.00 |
F14—P3—F15 | 88.9 (3) | C14—C15—H15A | 108.00 |
F14—P3—F16 | 89.4 (4) | C16—C15—H15B | 108.00 |
F15—P3—F17 | 90.7 (4) | H15A—C15—H15B | 107.00 |
F15—P3—F18 | 177.7 (4) | S2—C16—H16 | 108.00 |
F16—P3—F17 | 89.0 (4) | C17—C16—H16 | 108.00 |
F16—P3—F18 | 91.1 (4) | C15—C16—H16 | 108.00 |
Ag2—O1—C1 | 145.9 (4) | C16—C17—H17 | 110.00 |
Ag2—O4—C11 | 146.5 (5) | N3—C17—H17 | 111.00 |
Ag3ii—O7—C21 | 142.1 (4) | C18—C17—H17 | 110.00 |
Ag1—O16—C51 | 150.7 (5) | C17—C18—H18 | 110.00 |
C1—O2—H2O | 109.00 | N4—C18—H18 | 110.00 |
C11—O5—H5O | 109.00 | C19—C18—H18 | 110.00 |
C21—O8—H8O | 109.00 | S2—C19—H19B | 111.00 |
C31—O11—H11O | 110.00 | S2—C19—H19A | 111.00 |
C41—O13—H13O | 110.00 | H19A—C19—H19B | 109.00 |
C51—O17—H17O | 109.00 | C18—C19—H19A | 111.00 |
C7—N1—C10 | 113.0 (5) | C18—C19—H19B | 111.00 |
C8—N2—C10 | 112.3 (5) | C21—C22—H22A | 109.00 |
C17—N3—C20 | 112.4 (5) | C23—C22—H22B | 109.00 |
C18—N4—C20 | 112.2 (6) | C21—C22—H22B | 109.00 |
C27—N5—C30 | 115.3 (5) | C23—C22—H22A | 109.00 |
C28—N6—C30 | 113.2 (5) | H22A—C22—H22B | 108.00 |
C37—N7—C40 | 114.6 (6) | C24—C23—H23B | 109.00 |
C38—N8—C40 | 111.8 (6) | C22—C23—H23A | 109.00 |
C47—N9—C50 | 113.3 (5) | C22—C23—H23B | 109.00 |
C48—N10—C50 | 111.7 (5) | C24—C23—H23A | 109.00 |
C57—N11—C60 | 112.6 (5) | H23A—C23—H23B | 108.00 |
C58—N12—C60 | 113.5 (5) | C25—C24—H24A | 109.00 |
C7—N1—H1N | 115 (4) | H24A—C24—H24B | 108.00 |
C10—N1—H1N | 128 (4) | C23—C24—H24B | 109.00 |
C8—N2—H2N | 129 (5) | C25—C24—H24B | 109.00 |
C10—N2—H2N | 117 (5) | C23—C24—H24A | 109.00 |
C17—N3—H3N | 124 (4) | C24—C25—H25A | 108.00 |
C20—N3—H3N | 123 (4) | H25A—C25—H25B | 107.00 |
C20—N4—H4N | 124 (5) | C24—C25—H25B | 108.00 |
C18—N4—H4N | 124 (5) | C26—C25—H25A | 108.00 |
C30—N5—H5N | 117 (4) | C26—C25—H25B | 108.00 |
C27—N5—H5N | 127 (4) | C27—C26—H26 | 107.00 |
C28—N6—H6N | 119 (5) | S3—C26—H26 | 107.00 |
C30—N6—H6N | 127 (5) | C25—C26—H26 | 107.00 |
C40—N7—H7N | 134 (4) | C26—C27—H27 | 110.00 |
C37—N7—H7N | 110 (4) | N5—C27—H27 | 110.00 |
C38—N8—H8N | 114 (5) | C28—C27—H27 | 110.00 |
C40—N8—H8N | 128 (5) | N6—C28—H28 | 111.00 |
C50—N9—H9N | 117 (4) | C27—C28—H28 | 111.00 |
C47—N9—H9N | 126 (4) | C29—C28—H28 | 111.00 |
C50—N10—H10N | 132 (5) | S3—C29—H29B | 110.00 |
C48—N10—H10N | 110 (5) | C28—C29—H29A | 111.00 |
C57—N11—H11N | 134 (4) | S3—C29—H29A | 111.00 |
C60—N11—H11N | 111 (4) | C28—C29—H29B | 110.00 |
C58—N12—H12N | 105 (4) | H29A—C29—H29B | 109.00 |
C60—N12—H12N | 122 (4) | C31—C32—H32A | 109.00 |
O1—C1—O2 | 123.0 (5) | C33—C32—H32B | 109.00 |
O2—C1—C2 | 112.3 (5) | H32A—C32—H32B | 108.00 |
O1—C1—C2 | 124.6 (5) | C31—C32—H32B | 109.00 |
C1—C2—C3 | 112.8 (5) | C33—C32—H32A | 109.00 |
C2—C3—C4 | 115.3 (5) | C32—C33—H33A | 109.00 |
C3—C4—C5 | 112.6 (5) | H33A—C33—H33B | 108.00 |
C4—C5—C6 | 115.3 (5) | C32—C33—H33B | 109.00 |
S1—C6—C5 | 114.0 (5) | C34—C33—H33A | 109.00 |
C5—C6—C7 | 115.9 (5) | C34—C33—H33B | 109.00 |
S1—C6—C7 | 104.7 (4) | C33—C34—H34A | 109.00 |
N1—C7—C6 | 114.3 (5) | C33—C34—H34B | 109.00 |
N1—C7—C8 | 103.2 (5) | C35—C34—H34A | 109.00 |
C6—C7—C8 | 110.4 (5) | C35—C34—H34B | 109.00 |
C7—C8—C9 | 110.0 (5) | H34A—C34—H34B | 108.00 |
N2—C8—C7 | 102.9 (5) | H35A—C35—H35B | 107.00 |
N2—C8—C9 | 111.3 (6) | C34—C35—H35A | 108.00 |
S1—C9—C8 | 105.9 (4) | C36—C35—H35B | 108.00 |
O3—C10—N2 | 125.5 (6) | C36—C35—H35A | 108.00 |
O3—C10—N1 | 126.5 (6) | C34—C35—H35B | 108.00 |
N1—C10—N2 | 108.0 (5) | S4—C36—H36 | 108.00 |
O4—C11—O5 | 123.4 (6) | C37—C36—H36 | 108.00 |
O4—C11—C12 | 123.7 (6) | C35—C36—H36 | 108.00 |
O5—C11—C12 | 112.9 (5) | N7—C37—H37 | 110.00 |
C11—C12—C13 | 113.3 (6) | C36—C37—H37 | 110.00 |
C12—C13—C14 | 114.1 (6) | C38—C37—H37 | 110.00 |
C13—C14—C15 | 115.1 (6) | N8—C38—H38 | 111.00 |
C14—C15—C16 | 115.4 (5) | C37—C38—H38 | 111.00 |
S2—C16—C17 | 105.1 (4) | C39—C38—H38 | 111.00 |
S2—C16—C15 | 113.3 (5) | S4—C39—H39B | 110.00 |
C15—C16—C17 | 115.0 (5) | S4—C39—H39A | 110.00 |
C16—C17—C18 | 109.4 (5) | H39A—C39—H39B | 109.00 |
N3—C17—C18 | 102.5 (5) | C38—C39—H39A | 110.00 |
N3—C17—C16 | 113.3 (6) | C38—C39—H39B | 110.00 |
N4—C18—C17 | 103.1 (5) | H42A—C42—H42B | 108.00 |
N4—C18—C19 | 114.2 (6) | C41—C42—H42A | 109.00 |
C17—C18—C19 | 110.2 (6) | C41—C42—H42B | 109.00 |
S2—C19—C18 | 105.5 (5) | C43—C42—H42A | 109.00 |
O6—C20—N4 | 125.7 (6) | C43—C42—H42B | 109.00 |
N3—C20—N4 | 109.1 (6) | H43A—C43—H43B | 107.00 |
O6—C20—N3 | 125.3 (6) | C42—C43—H43B | 109.00 |
O7—C21—O8 | 122.3 (5) | C44—C43—H43A | 108.00 |
O7—C21—C22 | 123.8 (5) | C42—C43—H43A | 109.00 |
O8—C21—C22 | 113.9 (5) | C44—C43—H43B | 108.00 |
C21—C22—C23 | 113.0 (5) | C43—C44—H44A | 109.00 |
C22—C23—C24 | 114.0 (5) | C43—C44—H44B | 109.00 |
C23—C24—C25 | 112.3 (5) | C45—C44—H44A | 109.00 |
C24—C25—C26 | 116.2 (5) | C45—C44—H44B | 109.00 |
S3—C26—C25 | 113.2 (4) | H44A—C44—H44B | 108.00 |
S3—C26—C27 | 106.3 (4) | C46—C45—H45B | 108.00 |
C25—C26—C27 | 115.6 (5) | H45A—C45—H45B | 108.00 |
N5—C27—C28 | 101.8 (5) | C46—C45—H45A | 109.00 |
N5—C27—C26 | 114.9 (5) | C44—C45—H45A | 109.00 |
C26—C27—C28 | 108.7 (5) | C44—C45—H45B | 109.00 |
N6—C28—C29 | 112.3 (5) | S5—C46—H46 | 107.00 |
N6—C28—C27 | 102.4 (5) | C47—C46—H46 | 107.00 |
C27—C28—C29 | 109.1 (5) | C45—C46—H46 | 107.00 |
S3—C29—C28 | 106.1 (4) | N9—C47—H47 | 110.00 |
O9—C30—N6 | 126.0 (6) | C48—C47—H47 | 110.00 |
N5—C30—N6 | 106.4 (6) | C46—C47—H47 | 110.00 |
O9—C30—N5 | 127.6 (6) | C47—C48—H48 | 111.00 |
O11—C31—C32 | 110.9 (6) | N10—C48—H48 | 111.00 |
O10—C31—C32 | 126.5 (6) | C49—C48—H48 | 111.00 |
O10—C31—O11 | 122.5 (6) | H49A—C49—H49B | 109.00 |
C31—C32—C33 | 114.7 (7) | S5—C49—H49B | 111.00 |
C32—C33—C34 | 113.4 (6) | S5—C49—H49A | 111.00 |
C33—C34—C35 | 113.6 (6) | C48—C49—H49A | 111.00 |
C34—C35—C36 | 116.1 (6) | C48—C49—H49B | 111.00 |
C35—C36—C37 | 115.6 (6) | C51—C52—H52B | 109.00 |
S4—C36—C37 | 105.6 (6) | C51—C52—H52A | 109.00 |
S4—C36—C35 | 112.7 (5) | C53—C52—H52A | 109.00 |
N7—C37—C36 | 113.9 (6) | C53—C52—H52B | 109.00 |
N7—C37—C38 | 101.9 (6) | H52A—C52—H52B | 108.00 |
C36—C37—C38 | 109.8 (6) | C52—C53—H53B | 109.00 |
C37—C38—C39 | 109.4 (6) | C54—C53—H53A | 109.00 |
N8—C38—C37 | 102.0 (6) | C54—C53—H53B | 109.00 |
N8—C38—C39 | 112.7 (7) | C52—C53—H53A | 109.00 |
S4—C39—C38 | 107.7 (6) | H53A—C53—H53B | 108.00 |
N7—C40—N8 | 108.9 (6) | C53—C54—H54A | 110.00 |
O12—C40—N7 | 124.9 (6) | C53—C54—H54B | 110.00 |
O12—C40—N8 | 126.2 (6) | H54A—C54—H54B | 108.00 |
O13—C41—C42 | 113.5 (5) | C55—C54—H54B | 110.00 |
O13—C41—O14 | 122.6 (6) | C55—C54—H54A | 110.00 |
O14—C41—C42 | 123.9 (6) | C56—C55—H55B | 109.00 |
C41—C42—C43 | 111.6 (6) | C56—C55—H55A | 109.00 |
C42—C43—C44 | 114.9 (6) | C54—C55—H55B | 109.00 |
C43—C44—C45 | 111.1 (5) | C54—C55—H55A | 108.00 |
C44—C45—C46 | 114.8 (5) | H55A—C55—H55B | 108.00 |
S5—C46—C45 | 113.2 (5) | C55—C56—H56 | 108.00 |
S5—C46—C47 | 105.9 (4) | S6—C56—H56 | 108.00 |
C45—C46—C47 | 115.4 (5) | C57—C56—H56 | 108.00 |
N9—C47—C48 | 102.5 (5) | C58—C57—H57 | 111.00 |
N9—C47—C46 | 113.5 (5) | N11—C57—H57 | 111.00 |
C46—C47—C48 | 110.1 (5) | C56—C57—H57 | 111.00 |
C47—C48—C49 | 109.5 (5) | C59—C58—H58 | 111.00 |
N10—C48—C49 | 112.3 (5) | N12—C58—H58 | 111.00 |
N10—C48—C47 | 101.8 (5) | C57—C58—H58 | 111.00 |
S5—C49—C48 | 104.9 (4) | H59A—C59—H59B | 109.00 |
N9—C50—N10 | 108.4 (5) | S6—C59—H59A | 110.00 |
O15—C50—N9 | 126.1 (6) | S6—C59—H59B | 111.00 |
O15—C50—N10 | 125.5 (6) | C58—C59—H59A | 110.00 |
O17—C51—C52 | 111.6 (6) | C58—C59—H59B | 110.00 |
O16—C51—O17 | 123.8 (6) | ||
S2—Ag1—S1—C6 | 34.8 (3) | C47—N9—C50—O15 | −178.8 (6) |
S2—Ag1—S1—C9 | 129.7 (2) | C47—N9—C50—N10 | 0.7 (7) |
O16—Ag1—S1—C6 | −114.7 (3) | C50—N10—C48—C47 | −15.2 (7) |
O16—Ag1—S1—C9 | −19.8 (3) | C50—N10—C48—C49 | −132.2 (5) |
S1—Ag1—S2—C16 | 43.1 (3) | C48—N10—C50—O15 | −170.7 (6) |
S1—Ag1—S2—C19 | 138.1 (3) | C48—N10—C50—N9 | 9.8 (7) |
O16—Ag1—S2—C16 | −161.9 (3) | C60—N11—C57—C56 | 120.8 (5) |
O16—Ag1—S2—C19 | −66.9 (3) | C60—N11—C57—C58 | 4.0 (6) |
S1—Ag1—O16—C51 | 93.9 (10) | C57—N11—C60—O18 | 176.8 (6) |
S2—Ag1—O16—C51 | −71.9 (10) | C57—N11—C60—N12 | −2.9 (7) |
S4—Ag2—S3—C26 | 44.2 (2) | C60—N12—C58—C57 | 2.0 (7) |
S4—Ag2—S3—C29 | 137.4 (2) | C60—N12—C58—C59 | −115.9 (6) |
O1—Ag2—S3—C26 | −160.7 (2) | C58—N12—C60—O18 | −179.3 (6) |
O1—Ag2—S3—C29 | −67.6 (2) | C58—N12—C60—N11 | 0.4 (7) |
O4—Ag2—S3—C26 | −107.1 (3) | O1—C1—C2—C3 | −12.5 (9) |
O4—Ag2—S3—C29 | −13.9 (3) | O2—C1—C2—C3 | 166.1 (5) |
S3—Ag2—S4—C36 | 39.8 (3) | C1—C2—C3—C4 | 175.0 (5) |
S3—Ag2—S4—C39 | 134.0 (3) | C2—C3—C4—C5 | 178.7 (5) |
O1—Ag2—S4—C36 | −108.0 (3) | C3—C4—C5—C6 | −170.9 (5) |
O1—Ag2—S4—C39 | −13.8 (3) | C4—C5—C6—S1 | −55.7 (6) |
O4—Ag2—S4—C36 | −161.8 (3) | C4—C5—C6—C7 | −177.3 (5) |
O4—Ag2—S4—C39 | −67.6 (3) | S1—C6—C7—N1 | −89.7 (5) |
S3—Ag2—O1—C1 | −32.2 (7) | S1—C6—C7—C8 | 26.1 (6) |
S4—Ag2—O1—C1 | 130.9 (7) | C5—C6—C7—N1 | 36.8 (7) |
O4—Ag2—O1—C1 | −172.4 (8) | C5—C6—C7—C8 | 152.5 (5) |
S3—Ag2—O4—C11 | 117.5 (9) | N1—C7—C8—N2 | 5.9 (7) |
S4—Ag2—O4—C11 | −47.2 (9) | N1—C7—C8—C9 | 124.6 (5) |
O1—Ag2—O4—C11 | 174.6 (9) | C6—C7—C8—N2 | −116.6 (6) |
S6—Ag3—S5—C46 | 44.0 (3) | C6—C7—C8—C9 | 2.1 (7) |
S6—Ag3—S5—C49 | 137.9 (2) | N2—C8—C9—S1 | 83.5 (5) |
O7i—Ag3—S5—C46 | −158.3 (2) | C7—C8—C9—S1 | −30.0 (6) |
O7i—Ag3—S5—C49 | −64.3 (2) | O4—C11—C12—C13 | 107.8 (8) |
S5—Ag3—S6—C56 | 41.8 (3) | O5—C11—C12—C13 | −69.7 (7) |
S5—Ag3—S6—C59 | 136.3 (2) | C11—C12—C13—C14 | −62.1 (8) |
O7i—Ag3—S6—C56 | −113.2 (2) | C12—C13—C14—C15 | −65.0 (7) |
O7i—Ag3—S6—C59 | −18.7 (3) | C13—C14—C15—C16 | −65.4 (7) |
S5—Ag3—O7i—C21i | −30.9 (7) | C14—C15—C16—S2 | −58.6 (6) |
S6—Ag3—O7i—C21i | 139.7 (6) | C14—C15—C16—C17 | −179.6 (5) |
Ag1—S1—C6—C5 | −60.1 (5) | S2—C16—C17—N3 | −93.9 (5) |
Ag1—S1—C6—C7 | 67.5 (4) | S2—C16—C17—C18 | 19.9 (6) |
C9—S1—C6—C5 | −165.4 (5) | C15—C16—C17—N3 | 31.4 (7) |
C9—S1—C6—C7 | −37.7 (4) | C15—C16—C17—C18 | 145.1 (6) |
Ag1—S1—C9—C8 | −68.6 (4) | N3—C17—C18—N4 | 8.1 (7) |
C6—S1—C9—C8 | 39.6 (4) | N3—C17—C18—C19 | 130.4 (6) |
Ag1—S2—C16—C15 | −58.5 (5) | C16—C17—C18—N4 | −112.4 (6) |
Ag1—S2—C16—C17 | 67.8 (4) | C16—C17—C18—C19 | 9.9 (7) |
C19—S2—C16—C15 | −161.6 (5) | N4—C18—C19—S2 | 79.5 (7) |
C19—S2—C16—C17 | −35.2 (4) | C17—C18—C19—S2 | −36.0 (6) |
Ag1—S2—C19—C18 | −69.9 (5) | O7—C21—C22—C23 | −15.9 (9) |
C16—S2—C19—C18 | 41.6 (5) | O8—C21—C22—C23 | 166.1 (5) |
Ag2—S3—C26—C25 | −64.5 (4) | C21—C22—C23—C24 | 171.4 (5) |
Ag2—S3—C26—C27 | 63.4 (4) | C22—C23—C24—C25 | 179.9 (5) |
C29—S3—C26—C25 | −167.1 (5) | C23—C24—C25—C26 | −168.4 (5) |
C29—S3—C26—C27 | −39.2 (4) | C24—C25—C26—S3 | −54.3 (6) |
Ag2—S3—C29—C28 | −67.8 (4) | C24—C25—C26—C27 | −177.3 (5) |
C26—S3—C29—C28 | 42.2 (4) | S3—C26—C27—N5 | −87.8 (5) |
Ag2—S4—C36—C35 | −57.8 (6) | S3—C26—C27—C28 | 25.5 (5) |
Ag2—S4—C36—C37 | 69.3 (5) | C25—C26—C27—N5 | 38.8 (7) |
C39—S4—C36—C35 | −161.7 (6) | C25—C26—C27—C28 | 152.1 (5) |
C39—S4—C36—C37 | −34.6 (5) | N5—C27—C28—N6 | 7.5 (6) |
Ag2—S4—C39—C38 | −68.1 (6) | N5—C27—C28—C29 | 126.6 (5) |
C36—S4—C39—C38 | 39.4 (6) | C26—C27—C28—N6 | −114.2 (5) |
Ag3—S5—C46—C45 | −61.5 (5) | C26—C27—C28—C29 | 4.9 (7) |
Ag3—S5—C46—C47 | 65.8 (4) | N6—C28—C29—S3 | 79.1 (5) |
C49—S5—C46—C45 | −161.3 (5) | C27—C28—C29—S3 | −33.6 (6) |
C49—S5—C46—C47 | −34.0 (4) | O10—C31—C32—C33 | −7.2 (11) |
Ag3—S5—C49—C48 | −69.0 (4) | O11—C31—C32—C33 | 176.1 (6) |
C46—S5—C49—C48 | 41.1 (4) | C31—C32—C33—C34 | 76.4 (8) |
Ag3—S6—C56—C55 | −61.1 (5) | C32—C33—C34—C35 | −163.8 (6) |
Ag3—S6—C56—C57 | 64.4 (4) | C33—C34—C35—C36 | −64.8 (8) |
C59—S6—C56—C55 | −166.1 (5) | C34—C35—C36—S4 | −65.1 (7) |
C59—S6—C56—C57 | −40.6 (4) | C34—C35—C36—C37 | 173.4 (6) |
Ag3—S6—C59—C58 | −71.6 (4) | S4—C36—C37—N7 | −92.1 (7) |
C56—S6—C59—C58 | 38.3 (5) | S4—C36—C37—C38 | 21.4 (7) |
Ag2—O1—C1—O2 | −39.3 (11) | C35—C36—C37—N7 | 33.1 (9) |
Ag2—O1—C1—C2 | 139.2 (6) | C35—C36—C37—C38 | 146.7 (6) |
Ag2—O4—C11—O5 | −38.1 (13) | N7—C37—C38—N8 | 7.6 (7) |
Ag2—O4—C11—C12 | 144.6 (6) | N7—C37—C38—C39 | 127.2 (6) |
Ag3ii—O7—C21—O8 | −38.7 (10) | C36—C37—C38—N8 | −113.4 (6) |
Ag3ii—O7—C21—C22 | 143.5 (5) | C36—C37—C38—C39 | 6.1 (8) |
Ag1—O16—C51—O17 | −1.0 (15) | N8—C38—C39—S4 | 80.4 (7) |
Ag1—O16—C51—C52 | 178.0 (7) | C37—C38—C39—S4 | −32.4 (7) |
C10—N1—C7—C6 | 116.8 (6) | O13—C41—C42—C43 | 177.3 (6) |
C10—N1—C7—C8 | −3.1 (7) | O14—C41—C42—C43 | −5.0 (10) |
C7—N1—C10—O3 | 179.0 (6) | C41—C42—C43—C44 | 174.5 (6) |
C7—N1—C10—N2 | −1.4 (7) | C42—C43—C44—C45 | 169.2 (6) |
C10—N2—C8—C7 | −7.3 (8) | C43—C44—C45—C46 | −172.3 (6) |
C10—N2—C8—C9 | −125.1 (6) | C44—C45—C46—S5 | −61.4 (6) |
C8—N2—C10—O3 | −174.6 (6) | C44—C45—C46—C47 | 176.5 (5) |
C8—N2—C10—N1 | 5.7 (8) | S5—C46—C47—N9 | −96.6 (5) |
C20—N3—C17—C16 | 111.9 (6) | S5—C46—C47—C48 | 17.6 (6) |
C20—N3—C17—C18 | −5.9 (8) | C45—C46—C47—N9 | 29.4 (7) |
C17—N3—C20—O6 | −178.6 (6) | C45—C46—C47—C48 | 143.6 (5) |
C17—N3—C20—N4 | 0.9 (8) | N9—C47—C48—N10 | 14.1 (6) |
C20—N4—C18—C17 | −8.4 (8) | N9—C47—C48—C49 | 133.2 (5) |
C20—N4—C18—C19 | −127.9 (7) | C46—C47—C48—N10 | −106.9 (5) |
C18—N4—C20—O6 | −175.4 (7) | C46—C47—C48—C49 | 12.1 (7) |
C18—N4—C20—N3 | 5.1 (8) | N10—C48—C49—S5 | 75.6 (5) |
C30—N5—C27—C26 | 114.3 (6) | C47—C48—C49—S5 | −36.7 (6) |
C30—N5—C27—C28 | −2.9 (6) | O16—C51—C52—C53 | 6.8 (10) |
C27—N5—C30—O9 | 178.2 (6) | O17—C51—C52—C53 | −174.0 (6) |
C27—N5—C30—N6 | −3.3 (7) | C51—C52—C53—C54 | 176.9 (6) |
C30—N6—C28—C27 | −10.4 (7) | C52—C53—C54—C55 | 179.2 (6) |
C30—N6—C28—C29 | −127.2 (6) | C53—C54—C55—C56 | −168.5 (5) |
C28—N6—C30—O9 | −172.5 (6) | C54—C55—C56—S6 | −59.7 (6) |
C28—N6—C30—N5 | 9.0 (7) | C54—C55—C56—C57 | 178.6 (5) |
C40—N7—C37—C36 | 113.3 (7) | S6—C56—C57—N11 | −82.8 (5) |
C40—N7—C37—C38 | −4.9 (7) | S6—C56—C57—C58 | 31.5 (5) |
C37—N7—C40—O12 | 177.9 (6) | C55—C56—C57—N11 | 43.4 (7) |
C37—N7—C40—N8 | −0.5 (7) | C55—C56—C57—C58 | 157.7 (5) |
C40—N8—C38—C37 | −8.8 (8) | N11—C57—C58—N12 | −3.4 (6) |
C40—N8—C38—C39 | −125.9 (7) | N11—C57—C58—C59 | 116.4 (5) |
C38—N8—C40—O12 | −172.1 (6) | C56—C57—C58—N12 | −123.5 (5) |
C38—N8—C40—N7 | 6.2 (8) | C56—C57—C58—C59 | −3.7 (7) |
C50—N9—C47—C46 | 108.8 (6) | N12—C58—C59—S6 | 87.0 (5) |
C50—N9—C47—C48 | −9.9 (6) | C57—C58—C59—S6 | −25.6 (6) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···F17 | 0.88 (5) | 2.47 (5) | 3.211 (8) | 144 (5) |
N1—H1N···F18 | 0.88 (5) | 2.38 (5) | 3.231 (8) | 163 (6) |
N2—H2N···F4iii | 0.90 (5) | 2.45 (6) | 3.222 (9) | 144 (7) |
N2—H2N···F6iii | 0.90 (5) | 2.33 (4) | 3.100 (8) | 144 (7) |
O2—H2O···O12 | 0.84 | 1.84 | 2.672 (7) | 173 |
N3—H3N···F13iv | 0.88 (5) | 2.26 (5) | 2.960 (8) | 137 (5) |
N4—H4N···O14 | 0.87 (3) | 2.38 (7) | 2.978 (8) | 127 (6) |
N5—H5N···F12 | 0.88 (4) | 2.26 (4) | 3.119 (8) | 165 (5) |
O5—H5O···O9 | 0.84 | 1.84 | 2.655 (7) | 163 |
N6—H6N···F16 | 0.89 (3) | 2.23 (4) | 3.051 (7) | 154 (7) |
N7—H7N···F7iv | 0.87 (4) | 2.40 (4) | 3.138 (8) | 144 (5) |
N8—H8N···F14iv | 0.88 (4) | 2.52 (6) | 3.359 (9) | 159 (7) |
N8—H8N···F15iv | 0.88 (4) | 2.40 (6) | 3.169 (8) | 146 (7) |
O8—H8O···O18ii | 0.84 | 1.83 | 2.644 (6) | 163 |
N9—H9N···F1iii | 0.88 (4) | 2.46 (5) | 3.210 (8) | 143 (6) |
N10—H10N···F10i | 0.88 (3) | 2.34 (3) | 3.179 (8) | 159 (6) |
N11—H11N···F3v | 0.86 (5) | 2.31 (5) | 3.076 (7) | 148 (5) |
O11—H11O···O15ii | 0.84 | 1.76 | 2.578 (7) | 162 |
N12—H12N···F8vi | 0.87 (5) | 2.46 (6) | 3.252 (9) | 151 (5) |
N12—H12N···F9vi | 0.87 (5) | 2.49 (6) | 3.082 (8) | 126 (4) |
O13—H13O···O6 | 0.84 | 1.78 | 2.606 (7) | 168 |
O17—H17O···O3 | 0.84 | 1.80 | 2.630 (7) | 167 |
C4—H4A···O13vii | 0.99 | 2.55 | 3.291 (8) | 131 |
C6—H6···O13vii | 1.00 | 2.38 | 3.221 (8) | 141 |
C16—H16···O17iii | 1.00 | 2.35 | 3.270 (8) | 153 |
C24—H24B···O8viii | 0.99 | 2.54 | 3.155 (8) | 120 |
C26—H26···O18vii | 1.00 | 2.56 | 3.478 (8) | 152 |
C35—H35B···F7iv | 0.99 | 2.33 | 3.230 (11) | 151 |
C36—H36···O11ix | 1.00 | 2.21 | 3.197 (9) | 167 |
C38—H38···O9iv | 1.00 | 2.60 | 3.390 (9) | 136 |
C44—H44B···O2vii | 0.99 | 2.56 | 3.309 (8) | 132 |
C45—H45A···F2iii | 0.99 | 2.48 | 3.365 (9) | 149 |
C46—H46···O12vii | 1.00 | 2.49 | 3.431 (8) | 157 |
C56—H56···O5iii | 1.00 | 2.59 | 3.319 (8) | 130 |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) −x+1, y−1/2, −z+1; (iv) x, y−1, z; (v) −x+1, y−3/2, −z+1; (vi) x, y−1, z+1; (vii) −x+2, y+1/2, −z+1; (viii) −x+2, y+1/2, −z; (ix) −x+1, y−1/2, −z. |
[Ag(C10H16N2O3S)2](SbF6) | F(000) = 824 |
Mr = 832.24 | Dx = 1.976 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 11317 reflections |
a = 9.6902 (11) Å | θ = 1.4–27.3° |
b = 14.6452 (12) Å | µ = 1.90 mm−1 |
c = 9.8604 (12) Å | T = 173 K |
β = 91.167 (10)° | Block, colourless |
V = 1399.0 (3) Å3 | 0.35 × 0.15 × 0.09 mm |
Z = 2 |
Stoe IPDS 2 diffractometer | 5915 independent reflections |
Radiation source: fine-focus sealed tube | 5659 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 26.8°, θmin = 2.1° |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | h = −11→12 |
Tmin = 0.821, Tmax = 1.000 | k = −18→18 |
9320 measured reflections | l = −12→12 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.0413P)2 + 0.3385P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.064 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.77 e Å−3 |
5915 reflections | Δρmin = −0.56 e Å−3 |
376 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
5 restraints | Extinction coefficient: 0.0010 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 2830 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.003 (17) |
[Ag(C10H16N2O3S)2](SbF6) | V = 1399.0 (3) Å3 |
Mr = 832.24 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.6902 (11) Å | µ = 1.90 mm−1 |
b = 14.6452 (12) Å | T = 173 K |
c = 9.8604 (12) Å | 0.35 × 0.15 × 0.09 mm |
β = 91.167 (10)° |
Stoe IPDS 2 diffractometer | 5915 independent reflections |
Absorption correction: multi-scan (MULABS in PLATON; Spek, 2009) | 5659 reflections with I > 2σ(I) |
Tmin = 0.821, Tmax = 1.000 | Rint = 0.023 |
9320 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.064 | Δρmax = 0.77 e Å−3 |
S = 1.04 | Δρmin = −0.56 e Å−3 |
5915 reflections | Absolute structure: Flack (1983), with 2830 Friedel pairs |
376 parameters | Absolute structure parameter: 0.003 (17) |
5 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.71563 (3) | 0.77119 (2) | 0.40629 (3) | 0.0224 (1) | |
S1 | 0.79490 (10) | 0.92598 (6) | 0.46075 (10) | 0.0205 (2) | |
S2 | 0.66482 (10) | 0.61176 (6) | 0.44562 (10) | 0.0206 (3) | |
O1 | 0.4859 (4) | 0.9333 (2) | 1.1870 (3) | 0.0365 (10) | |
O2 | 0.6475 (3) | 0.8251 (2) | 1.1806 (3) | 0.0337 (10) | |
O3 | 1.0287 (3) | 0.64141 (19) | 0.4025 (3) | 0.0283 (9) | |
O4 | 0.8733 (4) | 0.6267 (2) | 1.1764 (3) | 0.0360 (10) | |
O5 | 0.8199 (4) | 0.4812 (2) | 1.2018 (3) | 0.0373 (10) | |
O6 | 0.4002 (3) | 0.8781 (2) | 0.4265 (3) | 0.0264 (9) | |
N1 | 1.0625 (3) | 0.7718 (3) | 0.5315 (3) | 0.0236 (9) | |
N2 | 1.0067 (4) | 0.7881 (2) | 0.3161 (3) | 0.0253 (10) | |
N3 | 0.4285 (3) | 0.7537 (2) | 0.5671 (3) | 0.0191 (9) | |
N4 | 0.3818 (4) | 0.7300 (3) | 0.3499 (3) | 0.0274 (9) | |
C1 | 0.5866 (4) | 0.8888 (3) | 1.1291 (4) | 0.0239 (11) | |
C2 | 0.6163 (5) | 0.9244 (3) | 0.9903 (4) | 0.0280 (12) | |
C3 | 0.7385 (4) | 0.8791 (3) | 0.9227 (4) | 0.0259 (11) | |
C4 | 0.7673 (4) | 0.9182 (3) | 0.7841 (4) | 0.0263 (12) | |
C5 | 0.8888 (4) | 0.8692 (3) | 0.7176 (4) | 0.0212 (10) | |
C6 | 0.9340 (4) | 0.9158 (3) | 0.5878 (4) | 0.0200 (10) | |
C7 | 1.0567 (4) | 0.8694 (3) | 0.5177 (4) | 0.0227 (11) | |
C8 | 1.0388 (4) | 0.8814 (3) | 0.3603 (4) | 0.0233 (11) | |
C9 | 0.9208 (5) | 0.9473 (3) | 0.3308 (4) | 0.0264 (11) | |
C10 | 1.0332 (4) | 0.7265 (3) | 0.4154 (4) | 0.0209 (9) | |
C11 | 0.8145 (4) | 0.5507 (3) | 1.1357 (4) | 0.0277 (12) | |
C12 | 0.7393 (5) | 0.5596 (4) | 1.0013 (5) | 0.0354 (14) | |
C13 | 0.8287 (4) | 0.6011 (3) | 0.8925 (4) | 0.0287 (12) | |
C14 | 0.7671 (4) | 0.5898 (3) | 0.7501 (4) | 0.0264 (12) | |
C15 | 0.6326 (4) | 0.6418 (3) | 0.7223 (4) | 0.0228 (11) | |
C16 | 0.5578 (4) | 0.6067 (3) | 0.5965 (4) | 0.0205 (10) | |
C17 | 0.4202 (4) | 0.6544 (3) | 0.5556 (4) | 0.0194 (10) | |
C18 | 0.3928 (4) | 0.6386 (3) | 0.4023 (4) | 0.0230 (11) | |
C19 | 0.5134 (4) | 0.5853 (3) | 0.3416 (4) | 0.0280 (12) | |
C20 | 0.4025 (4) | 0.7945 (3) | 0.4469 (4) | 0.0206 (11) | |
Sb1 | 0.23151 (3) | 0.72837 (2) | 0.94080 (3) | 0.0276 (1) | |
F1 | 0.0963 (4) | 0.6951 (3) | 0.8087 (4) | 0.0756 (14) | |
F2 | 0.3037 (4) | 0.8165 (2) | 0.8203 (3) | 0.0574 (11) | |
F3 | 0.3660 (6) | 0.7517 (6) | 1.0715 (4) | 0.150 (3) | |
F4 | 0.1645 (4) | 0.6392 (3) | 1.0583 (4) | 0.0623 (12) | |
F5 | 0.1067 (6) | 0.8090 (3) | 1.0187 (5) | 0.1075 (19) | |
F6 | 0.3428 (5) | 0.6371 (3) | 0.8630 (5) | 0.0905 (19) | |
H1N | 1.086 (5) | 0.743 (3) | 0.609 (3) | 0.0280* | |
H2A | 0.63410 | 0.99080 | 0.99680 | 0.0340* | |
H2B | 0.53310 | 0.91580 | 0.93170 | 0.0340* | |
H2N | 1.017 (5) | 0.772 (4) | 0.232 (3) | 0.0300* | |
H2O | 0.45690 | 0.90270 | 1.25260 | 0.0550* | |
H3A | 0.82170 | 0.88660 | 0.98160 | 0.0310* | |
H3B | 0.72010 | 0.81290 | 0.91360 | 0.0310* | |
H3N | 0.411 (5) | 0.783 (3) | 0.643 (3) | 0.0230* | |
H4A | 0.78880 | 0.98410 | 0.79300 | 0.0310* | |
H4B | 0.68380 | 0.91210 | 0.72530 | 0.0310* | |
H4N | 0.360 (5) | 0.745 (3) | 0.269 (3) | 0.0330* | |
H4O | 0.94680 | 0.61460 | 1.21950 | 0.0540* | |
H5A | 0.96790 | 0.86710 | 0.78270 | 0.0250* | |
H5B | 0.86160 | 0.80550 | 0.69660 | 0.0250* | |
H6 | 0.96380 | 0.97910 | 0.61270 | 0.0240* | |
H7 | 1.14570 | 0.89740 | 0.54990 | 0.0270* | |
H8 | 1.12630 | 0.90340 | 0.31930 | 0.0280* | |
H9A | 0.88010 | 0.93600 | 0.23940 | 0.0320* | |
H9B | 0.95380 | 1.01120 | 0.33530 | 0.0320* | |
H12A | 0.65660 | 0.59840 | 1.01290 | 0.0420* | |
H12B | 0.70760 | 0.49850 | 0.97110 | 0.0420* | |
H13A | 0.92080 | 0.57180 | 0.89650 | 0.0340* | |
H13B | 0.84150 | 0.66690 | 0.91160 | 0.0340* | |
H14A | 0.75010 | 0.52410 | 0.73370 | 0.0320* | |
H14B | 0.83620 | 0.61040 | 0.68400 | 0.0320* | |
H15A | 0.57180 | 0.63540 | 0.80130 | 0.0270* | |
H15B | 0.65330 | 0.70750 | 0.71080 | 0.0270* | |
H16 | 0.53620 | 0.54090 | 0.61280 | 0.0250* | |
H17 | 0.34240 | 0.63000 | 0.60990 | 0.0230* | |
H18 | 0.30410 | 0.60490 | 0.38720 | 0.0280* | |
H19A | 0.52770 | 0.60420 | 0.24650 | 0.0330* | |
H19B | 0.49440 | 0.51890 | 0.34330 | 0.0330* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0195 (1) | 0.0212 (1) | 0.0264 (1) | −0.0034 (1) | −0.0006 (1) | 0.0042 (1) |
S1 | 0.0211 (4) | 0.0193 (4) | 0.0211 (4) | 0.0012 (4) | −0.0001 (4) | 0.0008 (3) |
S2 | 0.0202 (4) | 0.0202 (4) | 0.0214 (5) | −0.0002 (4) | 0.0038 (4) | −0.0026 (3) |
O1 | 0.051 (2) | 0.0298 (16) | 0.0295 (16) | 0.0164 (15) | 0.0182 (15) | 0.0088 (13) |
O2 | 0.0339 (16) | 0.0432 (19) | 0.0239 (15) | 0.0151 (14) | −0.0009 (13) | 0.0097 (14) |
O3 | 0.0306 (15) | 0.0195 (14) | 0.0346 (17) | 0.0031 (12) | −0.0009 (13) | −0.0043 (12) |
O4 | 0.0406 (18) | 0.0329 (16) | 0.0337 (17) | −0.0079 (14) | −0.0153 (14) | 0.0012 (13) |
O5 | 0.051 (2) | 0.0288 (16) | 0.0316 (17) | −0.0018 (15) | −0.0105 (15) | −0.0001 (13) |
O6 | 0.0298 (15) | 0.0217 (15) | 0.0279 (15) | 0.0065 (12) | 0.0068 (12) | 0.0049 (11) |
N1 | 0.0269 (16) | 0.0218 (15) | 0.0221 (15) | 0.0051 (16) | 0.0014 (12) | 0.0005 (15) |
N2 | 0.0322 (17) | 0.0236 (18) | 0.0200 (16) | −0.0015 (13) | −0.0007 (14) | −0.0039 (13) |
N3 | 0.0233 (15) | 0.0145 (17) | 0.0197 (15) | 0.0028 (11) | 0.0022 (12) | −0.0008 (11) |
N4 | 0.0375 (18) | 0.0247 (16) | 0.0200 (15) | −0.0020 (18) | −0.0023 (13) | −0.0003 (17) |
C1 | 0.025 (2) | 0.0227 (19) | 0.024 (2) | −0.0023 (16) | 0.0001 (16) | −0.0018 (15) |
C2 | 0.036 (2) | 0.025 (2) | 0.023 (2) | 0.0042 (18) | 0.0043 (17) | 0.0033 (16) |
C3 | 0.032 (2) | 0.028 (2) | 0.0179 (19) | 0.0078 (17) | 0.0034 (16) | 0.0022 (15) |
C4 | 0.027 (2) | 0.028 (2) | 0.024 (2) | 0.0099 (17) | 0.0070 (16) | 0.0041 (17) |
C5 | 0.0215 (18) | 0.0210 (18) | 0.0212 (18) | 0.0003 (15) | 0.0036 (15) | −0.0026 (15) |
C6 | 0.0204 (18) | 0.0151 (17) | 0.0245 (19) | −0.0002 (14) | −0.0008 (15) | −0.0023 (14) |
C7 | 0.0199 (18) | 0.0223 (19) | 0.026 (2) | −0.0023 (16) | 0.0002 (15) | −0.0029 (16) |
C8 | 0.024 (2) | 0.0230 (19) | 0.023 (2) | −0.0059 (16) | 0.0038 (16) | −0.0012 (16) |
C9 | 0.034 (2) | 0.0194 (19) | 0.026 (2) | −0.0024 (16) | 0.0062 (17) | 0.0072 (15) |
C10 | 0.0155 (15) | 0.0212 (17) | 0.0261 (17) | 0.0031 (17) | 0.0035 (13) | −0.0005 (19) |
C11 | 0.027 (2) | 0.031 (2) | 0.025 (2) | −0.0028 (17) | 0.0007 (16) | −0.0022 (17) |
C12 | 0.030 (2) | 0.050 (3) | 0.026 (2) | −0.008 (2) | −0.0062 (18) | 0.003 (2) |
C13 | 0.025 (2) | 0.030 (2) | 0.031 (2) | 0.0006 (18) | 0.0006 (17) | 0.0023 (17) |
C14 | 0.027 (2) | 0.029 (2) | 0.023 (2) | 0.0040 (17) | −0.0014 (16) | 0.0072 (16) |
C15 | 0.0231 (18) | 0.025 (2) | 0.0202 (18) | 0.0015 (16) | 0.0016 (15) | 0.0024 (15) |
C16 | 0.0225 (18) | 0.0182 (17) | 0.0210 (18) | 0.0005 (15) | 0.0025 (15) | 0.0017 (14) |
C17 | 0.0174 (17) | 0.0176 (18) | 0.0233 (19) | −0.0027 (15) | 0.0028 (14) | 0.0019 (15) |
C18 | 0.0248 (19) | 0.0212 (19) | 0.023 (2) | −0.0052 (16) | −0.0023 (16) | −0.0030 (16) |
C19 | 0.030 (2) | 0.026 (2) | 0.028 (2) | −0.0031 (17) | 0.0019 (17) | −0.0102 (16) |
C20 | 0.0142 (16) | 0.026 (2) | 0.0216 (19) | 0.0036 (14) | 0.0039 (14) | 0.0002 (14) |
Sb1 | 0.0244 (1) | 0.0385 (2) | 0.0200 (1) | 0.0030 (1) | 0.0041 (1) | 0.0065 (1) |
F1 | 0.066 (2) | 0.110 (3) | 0.050 (2) | −0.047 (2) | −0.0189 (17) | 0.021 (2) |
F2 | 0.081 (2) | 0.0474 (19) | 0.0443 (18) | 0.0003 (18) | 0.0156 (17) | 0.0043 (15) |
F3 | 0.146 (4) | 0.259 (9) | 0.043 (2) | −0.130 (6) | −0.054 (3) | 0.065 (4) |
F4 | 0.057 (2) | 0.071 (2) | 0.060 (2) | 0.0077 (18) | 0.0270 (18) | 0.0360 (19) |
F5 | 0.150 (4) | 0.089 (3) | 0.087 (3) | 0.063 (3) | 0.091 (3) | 0.033 (3) |
F6 | 0.085 (3) | 0.080 (3) | 0.109 (4) | 0.047 (2) | 0.062 (3) | 0.049 (3) |
Sb1—F2 | 1.898 (3) | C6—C7 | 1.545 (6) |
Sb1—F3 | 1.846 (5) | C7—C8 | 1.568 (6) |
Sb1—F4 | 1.871 (4) | C8—C9 | 1.520 (6) |
Sb1—F5 | 1.867 (5) | C11—C12 | 1.505 (6) |
Sb1—F6 | 1.890 (5) | C12—C13 | 1.519 (6) |
Sb1—F1 | 1.892 (4) | C13—C14 | 1.524 (6) |
Ag1—S2 | 2.4192 (10) | C14—C15 | 1.530 (6) |
Ag1—S1 | 2.4496 (10) | C15—C16 | 1.514 (6) |
Ag1—O2i | 2.440 (3) | C16—C17 | 1.551 (6) |
S1—C9 | 1.814 (5) | C17—C18 | 1.547 (6) |
S1—C6 | 1.828 (4) | C18—C19 | 1.537 (6) |
S2—C16 | 1.832 (4) | C2—H2A | 0.9900 |
S2—C19 | 1.815 (4) | C2—H2B | 0.9900 |
O1—C1 | 1.314 (5) | C3—H3B | 0.9900 |
O2—C1 | 1.210 (5) | C3—H3A | 0.9900 |
O3—C10 | 1.253 (5) | C4—H4A | 0.9900 |
O4—C11 | 1.310 (5) | C4—H4B | 0.9900 |
O5—C11 | 1.209 (5) | C5—H5A | 0.9900 |
O6—C20 | 1.241 (5) | C5—H5B | 0.9900 |
O1—H2O | 0.8400 | C6—H6 | 1.0000 |
O4—H4O | 0.8400 | C7—H7 | 1.0000 |
N1—C10 | 1.348 (5) | C8—H8 | 1.0000 |
N1—C7 | 1.437 (6) | C9—H9B | 0.9900 |
N2—C10 | 1.352 (5) | C9—H9A | 0.9900 |
N2—C8 | 1.466 (5) | C12—H12A | 0.9900 |
N3—C17 | 1.461 (5) | C12—H12B | 0.9900 |
N3—C20 | 1.347 (5) | C13—H13B | 0.9900 |
N4—C20 | 1.356 (6) | C13—H13A | 0.9900 |
N4—C18 | 1.438 (6) | C14—H14B | 0.9900 |
N1—H1N | 0.90 (3) | C14—H14A | 0.9900 |
N2—H2N | 0.87 (3) | C15—H15A | 0.9900 |
N3—H3N | 0.88 (3) | C15—H15B | 0.9900 |
N4—H4N | 0.85 (3) | C16—H16 | 1.0000 |
C1—C2 | 1.498 (6) | C17—H17 | 1.0000 |
C2—C3 | 1.523 (6) | C18—H18 | 1.0000 |
C3—C4 | 1.513 (6) | C19—H19B | 0.9900 |
C4—C5 | 1.537 (6) | C19—H19A | 0.9900 |
C5—C6 | 1.523 (6) | ||
F3—Sb1—F5 | 92.9 (3) | N4—C18—C17 | 102.8 (3) |
F3—Sb1—F6 | 90.8 (3) | S2—C19—C18 | 106.5 (3) |
F4—Sb1—F5 | 87.18 (19) | N3—C20—N4 | 109.5 (4) |
F4—Sb1—F6 | 88.04 (19) | O6—C20—N3 | 125.7 (4) |
F5—Sb1—F6 | 173.8 (2) | O6—C20—N4 | 124.8 (4) |
F1—Sb1—F2 | 90.17 (16) | C1—C2—H2A | 109.00 |
F1—Sb1—F3 | 175.7 (3) | C1—C2—H2B | 109.00 |
F1—Sb1—F4 | 90.14 (18) | C3—C2—H2A | 109.00 |
F1—Sb1—F5 | 90.1 (2) | C3—C2—H2B | 109.00 |
F1—Sb1—F6 | 86.06 (19) | H2A—C2—H2B | 108.00 |
F2—Sb1—F3 | 92.7 (2) | C2—C3—H3B | 109.00 |
F2—Sb1—F4 | 178.34 (16) | C4—C3—H3A | 109.00 |
F2—Sb1—F5 | 94.45 (18) | C2—C3—H3A | 109.00 |
F2—Sb1—F6 | 90.36 (17) | H3A—C3—H3B | 108.00 |
F3—Sb1—F4 | 86.9 (2) | C4—C3—H3B | 109.00 |
S1—Ag1—S2 | 157.22 (4) | C3—C4—H4B | 109.00 |
S1—Ag1—O2i | 88.76 (7) | C3—C4—H4A | 109.00 |
S2—Ag1—O2i | 113.98 (7) | C5—C4—H4B | 109.00 |
Ag1—S1—C6 | 107.36 (14) | H4A—C4—H4B | 108.00 |
Ag1—S1—C9 | 102.52 (14) | C5—C4—H4A | 109.00 |
C6—S1—C9 | 90.06 (19) | H5A—C5—H5B | 108.00 |
Ag1—S2—C16 | 106.83 (14) | C6—C5—H5B | 109.00 |
Ag1—S2—C19 | 106.28 (14) | C4—C5—H5A | 109.00 |
C16—S2—C19 | 89.19 (18) | C4—C5—H5B | 109.00 |
Ag1ii—O2—C1 | 138.8 (3) | C6—C5—H5A | 109.00 |
C1—O1—H2O | 109.00 | C5—C6—H6 | 107.00 |
C11—O4—H4O | 110.00 | S1—C6—H6 | 107.00 |
C7—N1—C10 | 113.7 (3) | C7—C6—H6 | 107.00 |
C8—N2—C10 | 111.8 (3) | N1—C7—H7 | 110.00 |
C17—N3—C20 | 111.4 (3) | C6—C7—H7 | 110.00 |
C18—N4—C20 | 112.7 (3) | C8—C7—H7 | 110.00 |
C10—N1—H1N | 123 (3) | N2—C8—H8 | 111.00 |
C7—N1—H1N | 124 (3) | C7—C8—H8 | 111.00 |
C8—N2—H2N | 121 (4) | C9—C8—H8 | 111.00 |
C10—N2—H2N | 119 (4) | S1—C9—H9A | 111.00 |
C17—N3—H3N | 123 (3) | S1—C9—H9B | 111.00 |
C20—N3—H3N | 120 (3) | C8—C9—H9A | 111.00 |
C18—N4—H4N | 126 (3) | C8—C9—H9B | 111.00 |
C20—N4—H4N | 121 (3) | H9A—C9—H9B | 109.00 |
O1—C1—O2 | 124.1 (4) | C11—C12—H12A | 109.00 |
O2—C1—C2 | 123.4 (4) | C11—C12—H12B | 109.00 |
O1—C1—C2 | 112.5 (4) | C13—C12—H12A | 109.00 |
C1—C2—C3 | 114.5 (4) | C13—C12—H12B | 109.00 |
C2—C3—C4 | 113.0 (3) | H12A—C12—H12B | 108.00 |
C3—C4—C5 | 111.5 (3) | H13A—C13—H13B | 108.00 |
C4—C5—C6 | 112.7 (3) | C12—C13—H13A | 109.00 |
S1—C6—C7 | 107.0 (3) | C12—C13—H13B | 109.00 |
S1—C6—C5 | 113.1 (3) | C14—C13—H13A | 109.00 |
C5—C6—C7 | 114.6 (3) | C14—C13—H13B | 109.00 |
N1—C7—C8 | 102.0 (3) | C15—C14—H14A | 108.00 |
C6—C7—C8 | 108.8 (3) | C13—C14—H14A | 108.00 |
N1—C7—C6 | 115.1 (3) | C13—C14—H14B | 108.00 |
N2—C8—C9 | 112.4 (3) | C15—C14—H14B | 108.00 |
C7—C8—C9 | 109.2 (3) | H14A—C14—H14B | 108.00 |
N2—C8—C7 | 102.0 (3) | C16—C15—H15B | 109.00 |
S1—C9—C8 | 105.6 (3) | C14—C15—H15A | 109.00 |
O3—C10—N2 | 125.8 (4) | C14—C15—H15B | 109.00 |
N1—C10—N2 | 108.7 (4) | C16—C15—H15A | 109.00 |
O3—C10—N1 | 125.6 (4) | H15A—C15—H15B | 108.00 |
O4—C11—C12 | 113.3 (4) | S2—C16—H16 | 107.00 |
O4—C11—O5 | 122.4 (4) | C15—C16—H16 | 107.00 |
O5—C11—C12 | 124.2 (4) | C17—C16—H16 | 107.00 |
C11—C12—C13 | 112.6 (4) | N3—C17—H17 | 111.00 |
C12—C13—C14 | 112.9 (3) | C16—C17—H17 | 111.00 |
C13—C14—C15 | 115.3 (3) | C18—C17—H17 | 111.00 |
C14—C15—C16 | 111.7 (3) | N4—C18—H18 | 110.00 |
S2—C16—C15 | 112.5 (3) | C17—C18—H18 | 110.00 |
C15—C16—C17 | 117.1 (3) | C19—C18—H18 | 110.00 |
S2—C16—C17 | 105.6 (3) | S2—C19—H19A | 110.00 |
N3—C17—C16 | 112.5 (3) | S2—C19—H19B | 110.00 |
N3—C17—C18 | 103.5 (3) | C18—C19—H19A | 110.00 |
C16—C17—C18 | 108.4 (3) | C18—C19—H19B | 110.00 |
C17—C18—C19 | 109.9 (3) | H19A—C19—H19B | 109.00 |
N4—C18—C19 | 112.6 (3) | ||
S2—Ag1—S1—C6 | 31.81 (17) | C20—N4—C18—C19 | −116.3 (4) |
S2—Ag1—S1—C9 | 125.86 (17) | C18—N4—C20—O6 | 179.0 (4) |
O2i—Ag1—S1—C6 | −151.72 (15) | C18—N4—C20—N3 | 0.2 (5) |
O2i—Ag1—S1—C9 | −57.68 (16) | O1—C1—C2—C3 | 176.2 (4) |
S1—Ag1—S2—C16 | 52.15 (17) | O2—C1—C2—C3 | −5.0 (6) |
S1—Ag1—S2—C19 | 146.33 (15) | C1—C2—C3—C4 | −178.7 (4) |
O2i—Ag1—S2—C16 | −123.99 (15) | C2—C3—C4—C5 | −178.6 (3) |
O2i—Ag1—S2—C19 | −29.81 (16) | C3—C4—C5—C6 | −171.5 (3) |
S1—Ag1—O2i—C1i | −46.0 (4) | C4—C5—C6—S1 | −57.4 (4) |
S2—Ag1—O2i—C1i | 132.5 (4) | C4—C5—C6—C7 | 179.6 (3) |
Ag1—S1—C6—C5 | −59.8 (3) | S1—C6—C7—N1 | −93.2 (3) |
Ag1—S1—C6—C7 | 67.3 (3) | S1—C6—C7—C8 | 20.6 (4) |
C9—S1—C6—C5 | −162.9 (3) | C5—C6—C7—N1 | 33.0 (5) |
C9—S1—C6—C7 | −35.8 (3) | C5—C6—C7—C8 | 146.8 (3) |
Ag1—S1—C9—C8 | −66.6 (3) | N1—C7—C8—N2 | 12.2 (4) |
C6—S1—C9—C8 | 41.2 (3) | N1—C7—C8—C9 | 131.3 (3) |
Ag1—S2—C16—C15 | −62.9 (3) | C6—C7—C8—N2 | −109.9 (4) |
Ag1—S2—C16—C17 | 65.8 (3) | C6—C7—C8—C9 | 9.2 (5) |
C19—S2—C16—C15 | −169.7 (3) | N2—C8—C9—S1 | 77.4 (3) |
C19—S2—C16—C17 | −40.9 (3) | C7—C8—C9—S1 | −35.1 (4) |
Ag1—S2—C19—C18 | −67.8 (3) | O4—C11—C12—C13 | 51.6 (5) |
C16—S2—C19—C18 | 39.6 (3) | O5—C11—C12—C13 | −129.2 (5) |
Ag1ii—O2—C1—O1 | −30.8 (7) | C11—C12—C13—C14 | 166.3 (4) |
Ag1ii—O2—C1—C2 | 150.5 (3) | C12—C13—C14—C15 | 66.2 (5) |
C10—N1—C7—C6 | 109.4 (4) | C13—C14—C15—C16 | −163.7 (3) |
C10—N1—C7—C8 | −8.3 (4) | C14—C15—C16—S2 | −56.8 (4) |
C7—N1—C10—O3 | −178.4 (4) | C14—C15—C16—C17 | −179.3 (3) |
C7—N1—C10—N2 | 0.4 (4) | S2—C16—C17—N3 | −82.8 (3) |
C10—N2—C8—C7 | −13.2 (4) | S2—C16—C17—C18 | 31.0 (4) |
C10—N2—C8—C9 | −130.0 (4) | C15—C16—C17—N3 | 43.2 (5) |
C8—N2—C10—O3 | −172.5 (4) | C15—C16—C17—C18 | 157.0 (4) |
C8—N2—C10—N1 | 8.8 (5) | N3—C17—C18—N4 | −3.1 (4) |
C20—N3—C17—C16 | 120.3 (3) | N3—C17—C18—C19 | 117.0 (3) |
C20—N3—C17—C18 | 3.5 (4) | C16—C17—C18—N4 | −122.7 (4) |
C17—N3—C20—O6 | 178.8 (4) | C16—C17—C18—C19 | −2.6 (5) |
C17—N3—C20—N4 | −2.5 (4) | N4—C18—C19—S2 | 86.7 (3) |
C20—N4—C18—C17 | 1.9 (4) | C17—C18—C19—S2 | −27.3 (4) |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H2O···O6ii | 0.84 | 1.85 | 2.646 (4) | 158 |
O4—H4O···O3ii | 0.84 | 2.00 | 2.674 (4) | 137 |
N1—H1N···F1iii | 0.90 (3) | 2.09 (3) | 2.967 (5) | 165 (4) |
N2—H2N···F5iv | 0.87 (3) | 2.36 (3) | 3.122 (6) | 147 (5) |
N2—H2N···O4i | 0.87 (3) | 2.60 (6) | 3.014 (4) | 111 (4) |
N3—H3N···F2 | 0.88 (3) | 2.11 (4) | 2.944 (4) | 157 (4) |
N4—H4N···F3i | 0.85 (3) | 1.95 (3) | 2.765 (5) | 160 (4) |
C6—H6···O3v | 1.00 | 2.38 | 3.325 (5) | 157 |
C12—H12B···O1vi | 0.99 | 2.60 | 3.386 (6) | 137 |
C15—H15A···F6 | 0.99 | 2.31 | 3.158 (6) | 143 |
C16—H16···O1vi | 1.00 | 2.54 | 3.350 (5) | 138 |
C16—H16···O6vii | 1.00 | 2.49 | 3.381 (5) | 147 |
C17—H17···F6 | 1.00 | 2.50 | 3.148 (6) | 122 |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x+1, y, z−1; (v) −x+2, y+1/2, −z+1; (vi) −x+1, y−1/2, −z+2; (vii) −x+1, y−1/2, −z+1. |
Experimental details
(HL) | (I) | (II) | (IV) | |
Crystal data | ||||
Chemical formula | C10H16N2O3S | [Ag(C10H15N2O3S)]·3H2O | [Ag2(NO3)2(C10H16N2O3S)2]·H2O | [Ag(C10H16N2O3S)2](PF6) |
Mr | 244.31 | 405.22 | 846.39 | 741.46 |
Crystal system, space group | Orthorhombic, P212121 | Monoclinic, P21 | Monoclinic, C2 | Monoclinic, P21 |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 5.1955 (6), 10.3017 (17), 20.943 (2) | 8.7869 (8), 8.2847 (10), 9.8588 (10) | 21.8568 (12), 8.0321 (4), 16.8886 (9) | 15.1130 (7), 9.6028 (3), 28.6670 (13) |
α, β, γ (°) | 90, 90, 90 | 90, 95.718 (8), 90 | 90, 99.337 (4), 90 | 90, 90.946 (4), 90 |
V (Å3) | 1120.9 (2) | 714.12 (13) | 2925.6 (3) | 4159.8 (3) |
Z | 4 | 2 | 4 | 6 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.28 | 1.58 | 1.56 | 1.02 |
Crystal size (mm) | 0.50 × 0.13 × 0.13 | 0.40 × 0.40 × 0.15 | 0.29 × 0.27 × 0.22 | 0.37 × 0.25 × 0.24 |
Data collection | ||||
Diffractometer | Stoe IPDS 2 diffractometer | Stoe IPDS 2 diffractometer | Stoe IPDS 2 diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | Multi-scan (MULABS in PLATON; Spek, 2009) | Multi-scan (MULABS in PLATON; Spek, 2009) | Multi-scan (MULABS in PLATON; Spek, 2009) | Multi-scan (MULABS in PLATON; Spek, 2009) |
Tmin, Tmax | 0.841, 1.000 | 0.574, 0.810 | 0.878, 1.000 | 0.718, 0.818 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3715, 2102, 1871 | 8354, 3827, 3718 | 21197, 7861, 7163 | 43114, 14703, 13212 |
Rint | 0.047 | 0.024 | 0.024 | 0.038 |
(sin θ/λ)max (Å−1) | 0.609 | 0.686 | 0.687 | 0.609 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.090, 0.99 | 0.023, 0.061, 1.07 | 0.019, 0.041, 0.97 | 0.044, 0.109, 1.04 |
No. of reflections | 2102 | 3827 | 7861 | 14703 |
No. of parameters | 152 | 215 | 410 | 1123 |
No. of restraints | 2 | 18 | 7 | 13 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.25 | 0.43, −0.52 | 0.43, −0.50 | 1.54, −0.76 |
Absolute structure | Flack (1983), with 837 Friedel pairs | Flack (1983), with 1776 Friedel pairs | Flack (1983), with 3655 Friedel pairs | Flack (1983), with 6357 Friedel pairs |
Absolute structure parameter | −0.03 (9) | 0.00 (2) | −0.017 (10) | 0.02 (2) |
(V) | |
Crystal data | |
Chemical formula | [Ag(C10H16N2O3S)2](SbF6) |
Mr | 832.24 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 173 |
a, b, c (Å) | 9.6902 (11), 14.6452 (12), 9.8604 (12) |
α, β, γ (°) | 90, 91.167 (10), 90 |
V (Å3) | 1399.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.90 |
Crystal size (mm) | 0.35 × 0.15 × 0.09 |
Data collection | |
Diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | Multi-scan (MULABS in PLATON; Spek, 2009) |
Tmin, Tmax | 0.821, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9320, 5915, 5659 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.634 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.064, 1.04 |
No. of reflections | 5915 |
No. of parameters | 376 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.77, −0.56 |
Absolute structure | Flack (1983), with 2830 Friedel pairs |
Absolute structure parameter | 0.003 (17) |
Computer programs: X-AREA (Stoe & Cie, 2009), X-RED32 (Stoe & Cie, 2009), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C1—C2—C3—C4 | 175.51 (19) | C3—C4—C5—C6 | 73.2 (3) |
C2—C3—C4—C5 | 168.35 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.85 (2) | 2.24 (2) | 3.044 (3) | 158 (2) |
O1—H1O···O3ii | 0.84 | 1.72 | 2.544 (3) | 167 |
N2—H2N···O2iii | 0.86 (2) | 2.03 (2) | 2.881 (3) | 169 (2) |
C3—H3B···S1 | 0.99 | 2.74 | 3.328 (2) | 119 |
C6—H6···S1iv | 1.00 | 2.87 | 3.689 (2) | 139 |
C8—H8···O1v | 1.00 | 2.53 | 3.340 (3) | 138 |
Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1/2, −y+1, z−1/2; (iii) x+1/2, −y+3/2, −z; (iv) x+1, y, z; (v) x+1/2, −y+1/2, −z. |
Ag1—S1 | 2.5642 (7) | Ag1—S1iii | 2.5154 (7) |
Ag1—O3i | 2.5148 (18) | Ag1—O1Aii | 2.895 (4) |
Ag1—O2ii | 2.299 (2) | ||
S1—Ag1—O3i | 100.66 (4) | S1iii—Ag1—O3i | 82.03 (4) |
S1—Ag1—O2ii | 101.16 (8) | S1iii—Ag1—O2ii | 118.01 (9) |
S1—Ag1—S1iii | 130.36 (2) | Ag1—S1—Ag1iv | 130.04 (2) |
O2ii—Ag1—O3i | 124.54 (10) | ||
C1—C2—C3—C4 | 178.9 (3) | C3—C4—C5—C6 | −175.7 (2) |
C2—C3—C4—C5 | −179.9 (2) |
Symmetry codes: (i) x, y−1, z; (ii) x, y, z−1; (iii) −x+2, y−1/2, −z; (iv) −x+2, y+1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1Wv | 0.86 (3) | 2.06 (3) | 2.925 (4) | 179 (6) |
N2—H2N···O1Avi | 0.87 (3) | 2.09 (3) | 2.946 (6) | 166 (4) |
O1W—H1WA···O3W | 0.87 (4) | 1.88 (4) | 2.723 (6) | 163 (4) |
O1W—H1WB···O1A | 0.87 (5) | 1.98 (5) | 2.786 (6) | 153 (4) |
O2W—H2WA···O1W | 0.89 (3) | 2.27 (6) | 2.823 (5) | 120 (5) |
O2W—H2WA···O3W | 0.89 (3) | 2.45 (5) | 3.137 (7) | 135 (4) |
O2W—H2WB···O2vii | 0.89 (5) | 2.40 (7) | 2.935 (6) | 119 (6) |
O3W—H3WA···O1Av | 0.87 (5) | 2.24 (6) | 2.828 (7) | 125 (5) |
O3W—H3WB···O2Wv | 0.88 (3) | 2.27 (6) | 2.901 (7) | 128 (5) |
C4—H4A···O3i | 0.99 | 2.43 | 3.309 (3) | 148 |
C7—H7···O3viii | 1.00 | 2.38 | 3.325 (3) | 157 |
C8—H8···O3Wii | 1.00 | 2.52 | 3.397 (6) | 146 |
Symmetry codes: (i) x, y−1, z; (ii) x, y, z−1; (v) −x+1, y+1/2, −z+1; (vi) x, y+1, z−1; (vii) x−1, y, z; (viii) −x+1, y−1/2, −z. |
Ag1—S1 | 2.4851 (5) | Ag2—S1 | 2.4395 (4) |
Ag1—S2 | 2.4695 (5) | Ag2—S2i | 2.4638 (5) |
Ag1—O11 | 2.4529 (15) | Ag2—O21 | 2.3959 (15) |
Ag1—O12 | 2.6679 (15) | Ag2—O22 | 2.8007 (14) |
Ag1—O6i | 2.5243 (14) | Ag2—O3i | 2.5295 (14) |
S1—Ag1—S2 | 149.08 (2) | O6i—Ag1—O12 | 139.61 (5) |
S1—Ag1—O11 | 112.34 (4) | S1—Ag2—O21 | 105.35 (4) |
S1—Ag1—O12 | 91.72 (4) | S1—Ag2—S2i | 143.62 (2) |
S1—Ag1—O6i | 89.10 (3) | S1—Ag2—O3i | 98.66 (3) |
S2—Ag1—O11 | 96.79 (4) | S2i—Ag2—O21 | 109.39 (4) |
S2—Ag1—O12 | 99.78 (5) | O3i—Ag2—O21 | 89.23 (5) |
S2—Ag1—O6i | 99.92 (3) | S2i—Ag2—O3i | 92.34 (4) |
O11—Ag1—O12 | 49.89 (5) | Ag1—S1—Ag2 | 119.56 (2) |
O6i—Ag1—O11 | 92.93 (5) | Ag1—S2—Ag2ii | 116.09 (2) |
C1—C2—C3—C4 | 169.81 (18) | C11—C12—C13—C14 | −159.81 (18) |
C2—C3—C4—C5 | 171.54 (15) | C12—C13—C14—C15 | −74.6 (3) |
C3—C4—C5—C6 | 161.69 (14) | C13—C14—C15—C16 | 173.55 (17) |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O6i | 0.87 (3) | 2.13 (3) | 2.980 (2) | 166 (3) |
N1—H1N···O21ii | 0.84 (2) | 2.09 (2) | 2.899 (2) | 163 (2) |
O1—H1O···O5iii | 0.84 | 1.78 | 2.609 (2) | 167 |
O2W—H1W2···O3iv | 0.84 (3) | 2.06 (3) | 2.885 (2) | 168 (4) |
N2—H2N···O12iv | 0.872 (17) | 2.236 (18) | 3.026 (2) | 151 (2) |
N3—H3N···O22v | 0.863 (19) | 2.313 (19) | 3.103 (2) | 152 (2) |
N4—H4N···O11ii | 0.85 (2) | 2.15 (2) | 2.975 (2) | 164 (2) |
O4—H4O···O2vi | 0.84 | 1.79 | 2.619 (2) | 167 |
C2—H2B···O23vii | 0.99 | 2.45 | 3.384 (3) | 157 |
C8—H8···O13iv | 1.00 | 2.41 | 3.145 (2) | 130 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) x+1/2, y+1/2, z+1; (iv) −x+2, y, −z+1; (v) −x+2, y−1, −z+2; (vi) x−1/2, y−1/2, z−1; (vii) −x+5/2, y−1/2, −z+2. |
Ag1—S1 | 2.4232 (16) | Ag2—O1 | 2.517 (4) |
Ag1—S2 | 2.4524 (16) | Ag2—O4 | 2.623 (6) |
Ag1—O16 | 2.518 (5) | Ag3—S5 | 2.4752 (16) |
Ag1—O14 | 2.753 (5) | Ag3—S6 | 2.4270 (16) |
Ag2—S3 | 2.4655 (15) | Ag3—O7i | 2.491 (4) |
Ag2—S4 | 2.4600 (17) | Ag3—O10i | 2.981 (5) |
S1—Ag1—S2 | 151.54 (6) | S4—Ag2—O1 | 128.67 (11) |
S1—Ag1—O16 | 124.92 (14) | S4—Ag2—O4 | 78.40 (13) |
S2—Ag1—O16 | 80.41 (14) | O1—Ag2—O4 | 70.97 (16) |
S3—Ag2—S4 | 147.51 (6) | S5—Ag3—S6 | 157.56 (6) |
S3—Ag2—O1 | 80.10 (11) | S5—Ag3—O7i | 83.88 (11) |
S3—Ag2—O4 | 131.20 (13) | S6—Ag3—O7i | 116.73 (11) |
C1—C2—C3—C4 | 175.0 (5) | C31—C32—C33—C34 | 76.4 (8) |
C2—C3—C4—C5 | 178.7 (5) | C32—C33—C34—C35 | −163.8 (6) |
C3—C4—C5—C6 | −170.9 (5) | C33—C34—C35—C36 | −64.8 (8) |
C11—C12—C13—C14 | −62.1 (8) | C41—C42—C43—C44 | 174.5 (6) |
C12—C13—C14—C15 | −65.0 (7) | C42—C43—C44—C45 | 169.2 (6) |
C13—C14—C15—C16 | −65.4 (7) | C43—C44—C45—C46 | −172.3 (6) |
C21—C22—C23—C24 | 171.4 (5) | C51—C52—C53—C54 | 176.9 (6) |
C22—C23—C24—C25 | 179.9 (5) | C52—C53—C54—C55 | 179.2 (6) |
C23—C24—C25—C26 | −168.4 (5) | C53—C54—C55—C56 | −168.5 (5) |
Symmetry code: (i) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···F17 | 0.88 (5) | 2.47 (5) | 3.211 (8) | 144 (5) |
N1—H1N···F18 | 0.88 (5) | 2.38 (5) | 3.231 (8) | 163 (6) |
N2—H2N···F4ii | 0.90 (5) | 2.45 (6) | 3.222 (9) | 144 (7) |
N2—H2N···F6ii | 0.90 (5) | 2.33 (4) | 3.100 (8) | 144 (7) |
O2—H2O···O12 | 0.84 | 1.84 | 2.672 (7) | 173 |
N3—H3N···F13iii | 0.88 (5) | 2.26 (5) | 2.960 (8) | 137 (5) |
N4—H4N···O14 | 0.87 (3) | 2.38 (7) | 2.978 (8) | 127 (6) |
N5—H5N···F12 | 0.88 (4) | 2.26 (4) | 3.119 (8) | 165 (5) |
O5—H5O···O9 | 0.84 | 1.84 | 2.655 (7) | 163 |
N6—H6N···F16 | 0.89 (3) | 2.23 (4) | 3.051 (7) | 154 (7) |
N7—H7N···F7iii | 0.87 (4) | 2.40 (4) | 3.138 (8) | 144 (5) |
N8—H8N···F14iii | 0.88 (4) | 2.52 (6) | 3.359 (9) | 159 (7) |
N8—H8N···F15iii | 0.88 (4) | 2.40 (6) | 3.169 (8) | 146 (7) |
O8—H8O···O18iv | 0.84 | 1.83 | 2.644 (6) | 163 |
N9—H9N···F1ii | 0.88 (4) | 2.46 (5) | 3.210 (8) | 143 (6) |
N10—H10N···F10i | 0.88 (3) | 2.34 (3) | 3.179 (8) | 159 (6) |
N11—H11N···F3v | 0.86 (5) | 2.31 (5) | 3.076 (7) | 148 (5) |
O11—H11O···O15iv | 0.84 | 1.76 | 2.578 (7) | 162 |
N12—H12N···F8vi | 0.87 (5) | 2.46 (6) | 3.252 (9) | 151 (5) |
N12—H12N···F9vi | 0.87 (5) | 2.49 (6) | 3.082 (8) | 126 (4) |
O13—H13O···O6 | 0.84 | 1.78 | 2.606 (7) | 168 |
O17—H17O···O3 | 0.84 | 1.80 | 2.630 (7) | 167 |
C4—H4A···O13vii | 0.99 | 2.55 | 3.291 (8) | 131 |
C6—H6···O13vii | 1.00 | 2.38 | 3.221 (8) | 141 |
C16—H16···O17ii | 1.00 | 2.35 | 3.270 (8) | 153 |
C24—H24B···O8viii | 0.99 | 2.54 | 3.155 (8) | 120 |
C26—H26···O18vii | 1.00 | 2.56 | 3.478 (8) | 152 |
C35—H35B···F7iii | 0.99 | 2.33 | 3.230 (11) | 151 |
C36—H36···O11ix | 1.00 | 2.21 | 3.197 (9) | 167 |
C38—H38···O9iii | 1.00 | 2.60 | 3.390 (9) | 136 |
C44—H44B···O2vii | 0.99 | 2.56 | 3.309 (8) | 132 |
C45—H45A···F2ii | 0.99 | 2.48 | 3.365 (9) | 149 |
C46—H46···O12vii | 1.00 | 2.49 | 3.431 (8) | 157 |
C56—H56···O5ii | 1.00 | 2.59 | 3.319 (8) | 130 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y−1/2, −z+1; (iii) x, y−1, z; (iv) x, y, z−1; (v) −x+1, y−3/2, −z+1; (vi) x, y−1, z+1; (vii) −x+2, y+1/2, −z+1; (viii) −x+2, y+1/2, −z; (ix) −x+1, y−1/2, −z. |
Ag1—S2 | 2.4192 (10) | Ag1—O2i | 2.440 (3) |
Ag1—S1 | 2.4496 (10) | ||
S1—Ag1—S2 | 157.22 (4) | S2—Ag1—O2i | 113.98 (7) |
S1—Ag1—O2i | 88.76 (7) | ||
C1—C2—C3—C4 | −178.7 (4) | C11—C12—C13—C14 | 166.3 (4) |
C2—C3—C4—C5 | −178.6 (3) | C12—C13—C14—C15 | 66.2 (5) |
C3—C4—C5—C6 | −171.5 (3) | C13—C14—C15—C16 | −163.7 (3) |
Symmetry code: (i) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H2O···O6ii | 0.84 | 1.85 | 2.646 (4) | 158 |
O4—H4O···O3ii | 0.84 | 2.00 | 2.674 (4) | 137 |
N1—H1N···F1iii | 0.90 (3) | 2.09 (3) | 2.967 (5) | 165 (4) |
N2—H2N···F5iv | 0.87 (3) | 2.36 (3) | 3.122 (6) | 147 (5) |
N2—H2N···O4i | 0.87 (3) | 2.60 (6) | 3.014 (4) | 111 (4) |
N3—H3N···F2 | 0.88 (3) | 2.11 (4) | 2.944 (4) | 157 (4) |
N4—H4N···F3i | 0.85 (3) | 1.95 (3) | 2.765 (5) | 160 (4) |
C6—H6···O3v | 1.00 | 2.38 | 3.325 (5) | 157 |
C12—H12B···O1vi | 0.99 | 2.60 | 3.386 (6) | 137 |
C15—H15A···F6 | 0.99 | 2.31 | 3.158 (6) | 143 |
C16—H16···O1vi | 1.00 | 2.54 | 3.350 (5) | 138 |
C16—H16···O6vii | 1.00 | 2.49 | 3.381 (5) | 147 |
C17—H17···F6 | 1.00 | 2.50 | 3.148 (6) | 122 |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) x+1, y, z; (iv) x+1, y, z−1; (v) −x+2, y+1/2, −z+1; (vi) −x+1, y−1/2, −z+2; (vii) −x+1, y−1/2, −z+1. |
Compound | (I) | (VI) | (II) | (VII) | (IV) | (VIII) |
Molecular formula | C10H15AgN2O3S.3H2O | C10H15AgN2O3S.1.5H2O | C20H32Ag2N6O12S2.H2O | C10H16AgN3O6S.0.5H2O | C60H96Ag3N12O18S63+.3PF6- | C20H32AgN4O6S2+.PF6- |
Mr | 405.22 | 378.22 | 846.39 | 423.20 | 2224.37 | 741.46 |
System | Monoclinic | Orthorhombic | Monoclinic | Monoclinic | Monoclinic | Orthorhombic |
Space group | P21 | I222 | C2 | C2 | P21 | P21212 |
a (Å) | 8.7869 (8) | 17.586 (9) | 21.8568 (12) | 17.113 (6) | 15.1130 (7) | 15.136 (2) |
b (Å) | 8.2847 (10) | 21.245 (5) | 8.0321 (4) | 8.020 (2) | 9.6028 (3) | 9.744 (3) |
c (Å) | 9.8588 (10) | 8.019 (4) | 16.8886 (9) | 12.761 (4) | 28.6670 (13) | 9.719 (2) |
α (°) | 90 | 90 | 90 | 90 | 90 | 90 |
β (°) | 95.718 (8) | 90 | 99.337 (4) | 121.39 (3) | 90.946 (4) | 90 |
γ (°) | 90 | 90 | 90 | 90 | 90 | 90 |
V (Å3) | 714.12 (13) | 2996.0 | 2925.6 (3) | 1495.1 | 4159.8 (3) | 1433.4 |
Z | 2 | 8 | 4 | 4 | 2 | 2 |
Dcalc (Mg m-3) | 1.885 | 1.72 | 1.555 | 1.88 | 1.776 | 1.72 |
Ratio biotin:silver | 1:1 | 1:1 | 2:2; 1:1 | 1:1 | 6:3; 2:1 | 2:1 |
Volume (Å3)/Molecular unit | 357.1 | 374.5 | 731.4; 365.7 | 373.8 | 2079.9; 693.3 | 716.7 |
KPI (%) | 74.3 | 72.1 | 68.4 | 70.0 |
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Biotin, also known as vitamin H or B7, is an essential coenzyme which is biologically active only when it is covalently attached to the active site of biotin carboxylases. The latter are a class of important enzymes for fatty acid biosynthesis, gluconeogenesis and propionate catabolism (Knowles, 1989; Bagautdinov et al., 2005; Goodwin et al., 1998; Brady et al., 1966). Biotin also acts as a coenzyme for a number of enzymatic processes catalyzing the fixation and transfer of carbon dioxide. As shown by Moss & Lane (1971), in this process the carboxylate group of biotin is linked via the amide unit to the amino group of the lysine residue in the active site of the respective enzyme and a N1-carboxybiotinyl intermediate is formed. There are a number of different biotin-dependent carboxylases, all of which require divalent metal ions, such as Mg2+, Mn2+, Co2+, Zn2+ or Cu2+, for carboxylation of biotin with HCO3- and adenosine triphosphate (Moss & Lane, 1971; Wood & Zwolinski, 1976; Aoki & Saenger, 1983). The exact role of these tightly bound metal ions is not well understood (Griesser et al., 1973; Sigel et al., 1969).
Biotin (HL) has three possible binding sites for metal ions: the carboxylic acid group of the valeric acid side chain, the O atom of the ureido group and the S atom of the tetrahydrothiophene ring. It is normally thought that the coordination tendency of the ureido O atom is weak, while that of the S atom is more pronounced. Various authors have indicated that the thioether coordination could be stereoselective (Sigel et al., 1969; Griesser et al., 1973; Hadjiliadis & Pneumatikakis, 1979).
A search of the Cambridge Structural Database (CSD, Version 5.33, Update 4, August 2012; Allen, 2002) gave three hits for silver complexes of biotin [all three compounds are described in an abstract by Aoki & Saenger (1984) registered for the 13th General Assembly and International Congress of Crystallography, Hamburg, Germany, 1984]. The first complex is described as a biotin silver(I) sesquihydrate three-dimensional coordination polymer, (VI) (CSD refcode CIVGIX). The AgI cation is pentacoordinate, coordinated by four biotin molecules via two S atoms, one ureido O atom and two carboxyl O atoms of one molecule. The second is an AgNO3 two-dimensional coordination polymer, catena-[(µ2-biotin-O,S)nitratosilver(I) hemihydrate], (VII) (CSD refcode CEGKAA). This structure was published earlier by Aoki & Saenger (1983), and the AgI cation is described as being tetrahedrally coordinated by three different biotin molecules, via two S atoms and a ureido O atom, and by a nitrate O atom. However, bond-valence analysis [Brese & O'Keeffe, 1991; Brown, 2002; as implemented in PLATON (Spek, 2009)] indicates that the AgI cation is pentacoordinate with a long bond to a second nitrate O atom. The third complex is a bis(biotin) silver(I) hexaflorophosphate two-dimensional coordination polymer, (VIII) (CSD refcode CIVGET). The coordination environment of the AgI cation is described as tetrahedral, coordinated by four biotin molecules via two S atoms and by two carboxyl O atoms. As no atomic coordinates are available in the CSD for complexes (VI) and (VIII), it was not possible to verify the geometry of the silver(I) coordination environments for these two compounds.
Herein, we describe and compare the crystal structures of biotin and six chiral silver(I) coordination polymers, namely {[Ag(L)].3H2O}n, (I), {[Ag2(NO3)2(HL)2].H2O}n, (II), [Ag2(ClO4)2(HL)2]n, (III) (Altaf & Stoeckli-Evans, 2012), {[Ag(HL)2](PF6)}n, (IV), {[Ag(HL)2](SbF6)}n, (V), and {[Ag(NO3)(HL)].0.5H2O}n, (VII) (CSD refcode CEGKAA; Aoki & Saenger, 1983). The various coordination modes of biotin are compared and it is shown how these chiral coordination polymers form hydrogen-bonded networks, which rely on the presence of the counterions and, in certain compounds, the solvent water molecules.
We carried out a new low-temperature X-ray diffraction analysis of biotin (Fig. 1) and confirmed its absolute structure crystallographically for the first time [Flack parameter (Flack, 1983) = -0.03 (9)]. The bond lengths and angles are within the normal ranges and close to those reported previously for two independent room-temperature analyses reported by DeTitta et al. (1976). The conformational features are also very similar and we note here that: (a) the ureido ring [plane A = N1/C8/C7/N2/C10] is planar to within 0.026 (2) Å, with atom O3 displaced from this mean plane by 0.0785 (18) Å; (b) the tetrahydrothiophene ring (S1/C6–C9) has an envelope conformation with atom S1 at the flap and directed toward the ureido ring, as observed previously (Lett & Marquet, 1971; DeTitta et al., 1976, 1980). The S atom is displaced from the mean plane of atoms C6–C9 (plane B) by 0.8789 (6) Å; (c) the folding angle about bond C7—C8, defined as the dihedral angle involving planes A and B, is 58.89 (14)°; (d) The valeric acid side chain has a twisted conformation, with the C3—C4—C5—C6 torsion angle being 73.2 (3)° (Table 1); and (e) the C3 methylene group is involved in an intramolecular C—H···S interaction (Fig. 1 and Table 2).
In the crystal structure of biotin, molecules are linked head-to-tail via O—H···O and N—H···O hydrogen bonds involving the carboxylic acid group, one of the N-bound H atoms and the ureido carbonyl O atom (Table 2). This gives a classical C═ O···H—N ring arrangement with an R22(8) ring motif (Bernstein et al., 1995), forming zigzag chains propagating along [001]. These chains are linked via an N—H···O hydrogen bond involving the other N-bound H atom of the ureido group and a carboxyl O atom. This results in the formation of a two-dimensional undulating sheet-like arrangement (Fig. 2) lying parallel to (100), which is further stabilized by a C—H···S interaction (Table 2). These sheets are in turn linked via C—H···O interactions to form a three-dimensional network (Table 2).
In (I), {[Ag(L)].3H2O}n, prepared by the reaction of biotin with silver acetate and a few drops of aqueous ammonia, the valeric acid group is deprotonated (Fig. 3). Atom Ag1 is coordinated by four biotin molecules, two via the S atom of a tetrahydrothiophene ring, one via a ureido group O atom and one via two carboxyl O atoms of the same molecule (Table 3). This leads to the formation of a two-dimensional network lying parallel to the bc plane (Fig. 4). In (VI) mentioned above, the structure is described as a three-dimensional coordination polymer. In (I), the geometric environment around the silver(I) cation as indicated by bond-valence analysis is pentacoordinate. The bicyclic system of the biotin molecule is folded along the C7—C8 bond, with the dihedral angle between planes A and B being 57.62 (17)°, which is slightly smaller than that found in biotin itself [58.89 (14)°]. The valeric acid side chain has an extended conformation (Table 3).
In the crystal structure of (I), the two-dimensional networks are linked via N—H···O and O—H···O hydrogen bonds involving the carboxyl O atoms and the solvent water molecules (Fig. 5 and Table 4). There are also C—H···O and C—H···N interactions present, leading ultimately to the formation of a three-dimensional network (Table 4).
Compound (II), {[Ag2(NO3)2(HL)2].H2O}n, synthesized by the reaction of biotin with silver(I) nitrate, is a one-dimensional coordination polymer (Figs. 6 and 7a). The structure is similar to that of the known silver(I) nitrate complex, {[Ag(NO3)(HL)].0.5H2O}n, (VII), described above (CEGKAA; Aoki & Saenger, 1983) (see Fig. 7b). On comparing the structures of the two compounds (cf. Figs. 7a and 7b), it can be seen that (II) is composed of two independent biotin molecules, two independent AgI cations and one solvent water molecule, while (VII) is composed of one biotin molecule, one AgI cation and one half of a solvent water molecule.
In (II), atom Ag1 is coordinated by three biotin molecules, twice via an S atom and once via a ureido O atom, and by the nitrate O atoms, which coordinate in a bidentate manner; the Ag1—Onitrate distances are 2.4529 (15) and 2.6679 (15) Å, while the Ag2—Onitrate distances are 2.3959 (15) and 2.8007 (14) Å. This leads to a pentacoordination mode for the two AgI cations (Table 5), similar to the situation in (VII), where the Ag—Onitrate distances are 2.45 (4) and 2.82 (4) Å.
In (II), the two valeric acid side chains have different conformations, one twisted, with the torsion angle C12—C13—C14—C15 being -74.6 (3)°, and the other extended (Table 5). In (VII) this chain has an extended arrangement. In (II) the bicyclic units are folded, with the dihedral angles between planes A and B being 59.14 (12) and 59.27 (12)°, similar to that in biotin itself.
In the crystal structure of (II), the acid groups are linked via C═ O···H—O hydrogen bonds, generating R22(8) ring motifs. The presence of O—H···O and N—H···O hydrogen bonds leads to the formation of a three-dimensional network (Fig. 8 and Table 6). There are also C—H···O interactions present (Table 6).
The crystal structure of the silver perchlorate complex of biotin, [Ag2(ClO4)2(HL)2]n, (III), has been reported elsewhere (Altaf & Stoeckli-Evans, 2012). The crystals were twinned and gave a poor set of diffraction data. However, the overall structure is similar to that of (II). There are two independent AgI cations coordinated by three biotin molecules, via two S atoms and a ureido O atom, and by an O atom of a perchlorate anion. Hence, the two AgI cations of (III) have distorted tetrahedral coordination environments. This leads to the formation of a one-dimensional polymer chain similar to that observed for (II). Here too one of the valeric acid chains is in an extended conformation while the other is twisted (Fig. 9).
In the crystal structure of (III), the chains are linked via pairs of O—H···O hydrogen bonds involving the carboxylic acid groups, with R22(8) ring motifs, forming a two-dimensional network lying parallel to the ab plane. There are also N—H···O hydrogen bonds involving the perchlorate O atoms, not only within the chains but also linking the chains, which together with the inter-chain O—H···O hydrogen bonds leads to the formation of a three-dimensional network.
Complex (IV), {[Ag(HL)2](PF6)}n, prepared by the reaction of biotin with AgPF6 in a 1:2 molar ratio, is composed of three independent silver(I) cations and six independent biotin molecules (Fig. 10a). All three AgI cations, Ag1, Ag2 and Ag3, have a distorted tetrahedral coordination geometry, being coordinated by four biotin molecules, two via the S atoms and two via carboxyl O atoms of two different biotin molecules (Table 7). This leads to the formation of a double-stranded helical chain (Fig. 10b). In (VIII) (CIVGET), the AgPF6 complex of biotin mentioned above, the structure is described as a two-dimensional coordination polymer, the AgI cation coordinated by four biotin molecules in the same manner as in (IV), with a tetrahedral coordination environment.
The presence of O—H···O hydrogen bonds in (IV), involving the acid OH group and the ureido O atom, stabilizes the polymeric chain structure (Fig. 9b). The conformations of the valeric acid side chains involving atoms C1–C4, C21–C24, C41–44 and C51–C54 are extended, different from those involving atoms C11–C14 and C31–C34 which are twisted (Table 7). The bicyclic units are folded, with the dihedral angles involving planes A and B varying from 58.3 (4) to 59.9 (4)°, again similar to that in biotin itself.
In the crystal structure of (IV), there are N—H···F hydrogen bonds involving the PF6- anions (Fig. 11 and Table 8), which result in the formation of two-dimensional slab-like structures lying parallel to (011). These slabs are in turn connected via C—H···O and C—H···F interactions, forming a three-dimensional network (Table 8).
The asymmetric unit of the silver(I) coordination polymer, {[Ag(HL)2](SbF6)}n, (V), is illustrated in Fig. 12(a). The silver(I) cation is coordinated by three biotin molecules in a trigonal-planar geometry. Two of the three biotin molecules coordinate to atom Ag1 via the S atom of the tetrahydrothiophene group, while the third is coordinated via a carboxyl O atom of the valeric acid side chain (Table 9). This results in the formation of a chiral double-stranded helical chain, stabilized by O—H···O and N—H···O hydrogen bonds (Fig. 12b and Table 10). The conformations of the two valeric acid side chains are different, one extended and one twisted, and similar to those observed in (IV) (Table 9). The bicyclic units are folded, with the dihedral angles involving planes A and B being 59.2 (3) and 59.8 (3)°, respectively.
In the crystal of (V), N—H···F hydrogen bonds involving the SbF6- anions are also present (Fig. 13 and Table 10), resulting in the formation of two-dimensional slab-like structures lying parallel to (101). These slabs are in turn connected via C—H···O and C—H···F interactions, forming a three-dimensional network. This arrangement is similar to that observed for (IV).
In conclusion, the absolute configuration of biotin and complexes (I), (II), (IV) and (V) has been confirmed crystallographically by resonant scattering. The coordinates of each compound correspond to the absolute structure of the molecule in the crystal.
We now compare these four new chiral, one- and two-dimensional coordination polymers with each other. [Rephrasing OK?] In (I), (II) and (III), two silver(I) cations are bridged by an S atom. The Ag—S—Ag bridging angle in (I) is 130.04 (12)°. This is much larger than the same angles observed in (II) and (III), which vary from 116.09 (2) to 119.56 (2)°. In (II), (IV) and (V) the Ag—S distances vary from 2.4192 (10) to 2.4851 (5) Å, while in (I) these distances are considerably longer, 2.5154 (7) and 2.5642 (7) Å. In (III) there are both short and long Ag—S bonds present, that is 2.438 (6) and 2.517 (6) for Ag1, and 2.441 (6) and 2.519 (6) for Ag2. In (VII) these distances are 2.39 (1) and 2.52 (1) Å, similar to the situation in (III).
In (I), (II) and (III) the AgI cation is coordinated by the ureido O atom, with similar Ag—O distances in (I) [2.5148 (18) Å] and (II) [2.5243 (14) and 2.5295 (14) Å] but with significantly shorter distances in (III) [2.338 (1) and 2.392 (17) Å]. The longest distance [2.68 (3) Å] is reported for (VII). In (I), the carboxylic acid group is deprotonated and it coordinates to the silver(I) cation with a short Ag1—O2ii distance of only 2.299 (2) Å [symmetry code: (ii) x, y, z - 1]. In (IV), two of the six valeric acid groups are deprotonated and coordinate to the silver(I) cations with Ag—O distances of 2.491 (4) and 2.623 (6) Å, while in (V) the same distance is 2.440 (3) Å.
All the tetrahydrothiophene rings have envelope conformations, with the displacement of the S atom from the mean plane of the four C atoms (plane B) varying from 0.781 (1) to 0.926 (6) Å. The O atom of the ureido group is coordinated to an AgI cation in (I), (II) and (III), and is displaced from the five-membered ring (plane A) by as much as 0.156 (2) Å [In which compound?]. In (IV) and (V) it is not coordinated to the silver(I) cation and the displacement is only ca 0.05 Å. The conformation of the bicyclic tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one entity in the various complexes is similar, with the dihedral angles involving planes A and B varying only slightly, from 57.62 (17) to 59.9 (4)°. This is similar to the value observed for biotin itself [58.89 (14)°].
The most significant differences occur in the conformation of the valeric acid side chains. The torsion angles along the chains indicate that in (II)–(V) one of the pair of chains is twisted, as in biotin itself, while the other pair of chains is in an extended conformation, as is the chain in (I) and (VII).
In (II), and (III) and (VII), prepared with potentially coordinating anions, viz. nitrate and perchlorate, respectively, they do indeed coordinate to the silver(I) cations and are also involved in intra- and interchain N—H···O hydrogen bonds. In comparison, in (IV) and (V), the PF6- and SbF6- anions, respectively, do not coordinate to the AgI cations but participate in intermolecular N—H···F and C—H···F interactions.
The coordination environment around the AgI cations varies between the structures. It is AgS2O distorted trigonal planar in (V), AgS2O2 distorted tetrahedral in (III) and (IV), and AgS2O3 pentacoordinate, distorted square pyramidal, in (I), (II) and (VII). The AgI cation in (VI) is reported to be pentacoordinate (AgS2O3), while in (VIII) it is reported to be tetrahedral (AgS2O2).
In the crystal structures of (I)–(V) and (VII), the one- and two-dimensional polymers are linked via a series of classical and non-classical hydrogen bonds, forming three-dimensional networks.
Crystallographic details of (I) and (VI), (II) and (VII), and (IV) and (VIII), are compared in Table 11. In (I) and (VI), the ratio of biotin to silver is 1:1, with three solvent water molecules for (I) and 1.5 for (VI). While (I) is a two-dimensional polymer, (VI) is described as a three-dimensional network. However, in both compounds the AgI cations have pentacoordination environments, being coordinated by four biotin molecules via two S atoms, a ureido O atom and two carboxyl O atoms of one molecule. They crystallize in space groups P21 (Z = 2) and I222 (Z = 8), respectively. The volume occupied by the molecular unit (silver:biotin) and the density are 357.1 Å3 and 1.885 Mg m-3, respectively, for (I), compared with 374.5 Å3 and 1.721 Mg m-3, respectively, for (VI).
Compounds (II) and (VII) crystallize in the same monoclinic space group, C2. In both compounds the biotin:silver ratio is 1:1 and the AgI cations have pentacoordination environments, being coordinated by three biotin molecules via two S atoms and a ureido O atom, and by two nitrate O atoms. The volume occupied by the molecular unit (silver:biotin) and the density are, respectively, 365.7 Å3 and 1.555 Mg m-3 for (II), and 373.77 Å3 and 1.88 Mg m-3 for (VII).
Compounds (IV) and (VIII) have the same biotin:silver ratio (2:1). In both compounds the AgI cations have tetrahedral coordination environments, being coordinated by four biotin molecules via two S atoms and two carboxyl O atoms. They crystallize in space groups P21 (Z = 2) and P21212 (Z = 2; this complex possesses two-fold rotation symmetry), respectively. The volume occupied by the molecular unit (2biotin:silver) and the density are, respectively, 693.3 Å3 and 1.776 Mg m-3 for (IV), and 716.7 Å3 and 1.72 Mg m-3 for (VIII). Compound (IV) is a double-stranded helical chain, while (VIII) is described as a two-dimensional coordination polymer.
Further work will entail efforts to synthesize (VI), (VII) and (VIII) to determine if they are polymorphs of (I), (II) and (IV), respectively, and to examine the possibility of phase transformations taking place on cooling. Crystals of (VI)–(VIII) were measured at room temperature, while those of (I), (II) and (IV) were measured at 173 K. Compounds (II) and (VII), for example, both crystallize in space group C2 and the length of the unique b axis is almost the same, while the volume of the unit cell of (II) is almost twice that of (VII). Interestingly, the simulated X-ray powder patterns (routine SimPowderP in PLATON; Spek, 2009) of (II) and (VII) are very similar concerning peak positions and relative intensity. Hence, it may be possible that (II) is the result of a phase transformation giving a k2 subgroup at lower temperature. It is also possible that these structures are different simply due to the presence of different conformations of the valeric acid side chains. The packing indices [KPI (Kitajgorodskij, 1973), calculated using PLATON (Spek, 2009)] are 72.1 and 68.4% for (II) and (VII), respectively, with both extended and twisted valeric acid side chains in (II) but only extended in (VII) (see Fig. 7). The highest value of 74.3% is observed for the two-dimensional coordination polymer, (I), where the valeric acid side chain has an extended conformation (Fig. 4).