(Acetonitrile-κN)(3-amino-4-methyl­benzene­sulfonato-κN)aqua­(triphenyl­phosphine-κP)silver(I) hemihydrate

The title compound, [Ag(C₇H₈NO₃S)(C₂H₃N)(C₁₈H₁₅P)(H₂O)]·0.5H₂O, has a mononuclear structure in which the Ag^I ion is four-coordinated by the N atoms from a 3-amino-4-methyl­benzene­sulfonate anion and an acetonitrile mol­ecule, one P atom from a triphenyl­phosphine ligand and one O atom from a water mol­ecule, forming a distorted tetra­hedral configuration. Mol­ecules are linked into a ribbon-like structure along the a axis by O(water)—H...O hydrogen bonds involving the coordinated water mol­ecule, and N—H...O hydrogen bonds. The uncoordinated water mol­ecule is disordered across an inversion centre.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.035
• wR factor = 0.110
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.73 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.51 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        500 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        500 Deg.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT415_ALERT_2_C Short Inter D-H..H-X       H2W2   ..  H27B    ..       2.13 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C24    ..  C24     ..       3.18 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.854(10) ......       3.00 su-Ra
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.853(10) ......       3.00 su-Ra
              O1W  -H1W2    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.854(10) ......       3.00 su-Ra
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.853(10) ......       3.00 su-Ra
              O1W  -H2#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.95(3), Rep   1.952(13) ......       2.31 su-Ra
              H1#  -O2      1.555   2.667
PLAT736_ALERT_1_C H...A   Calc     2.09(3), Rep   2.091(12) ......       2.50 su-Ra
              H2#  -O3      1.555   1.655

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         15

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

  13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Recently, intense interest has been focused on silver(I) sulfonates because of their interesting structures and properties (Han & Li, 2007a). So far, some silver(I) sulfonate compounds modified by secondary ligands that display different structures have been reported (Han & Li, 2007b). We selected 3-amino-4-methylbenzenesulfonic acid (HL) as a sulfonate ligand and triphenylphosphine (TPP) as a secondary ligand, generating a new coordination complex, [Ag(L)(TPP)(CNCH₃)(H₂O)].0.5H₂O, which is reported here.

In compound (I), each Ag^I cation is four-coordinated by two N atoms one each from a 3-amino-4-methylbenzenesulfonate anion and a acetonitrile molecule, one P atom from a triphenylphosphine ligand, and one O atom from the water molecule, forming a distorted tetrahedral configuration (Fig. 1). The Ag—N (sulfonate) distance of the title complex is comparable to that found in a related structure (Han & Li, 2007b). The molecules are linked through O_w—H···O and N—H···O hydrogen bonds (Table 2) to form a ribbon like structure along the a axis.

Related literature

For studies on silver sulfonates, see: Han & Li (2007a,b).

S2. Experimental

An aqueous solution (12 ml) of 3-amino-4-methylbenzenesulfonic acid (0.5 mmol) was added to solid Ag₂CO₃ (0.25 mmol) and stirred for several minutes until no further CO₂ was given off. Triphenylphosphine (0.5 mmol) in acetonitrile (5 ml) was then added and a solution formed. Crystals of the title compound were obtained by slow evaporation of the solvent for several days at room temperature.

S3. Refinement

The amino H atoms were located in a difference map, and were refined with distance restraints of N—H = 0.90 (1) Å and H···H = 1.37 (2) Å, and with U_iso(H) = 1.5U_eq(N). H-atoms of the water molecules were located in a difference map, and were refined with distance restraints of O–H = 0.85 (1) Å and H···H = 1.39 (2) Å, and with U_iso(H) = 1.5U_eq(N). C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with U(H) = 1.2–1.5U_eq(C). Atom O2W is disordered across an inversion centre and it was refined with an occupancy of 0.50. The U^ij components of O2W were approximated to isotropic behaviour.

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

(Acetonitrile-κN)(3-amino-4-methylbenzenesulfonato- κN)aqua(triphenylphosphine-κP)silver(I) hemihydrate

Crystal data

[Ag(C7H8NO3S)(C2H3N)(C18H15P)(H2O)]·0.5H2O	Z = 2
Mr = 624.42	F(000) = 638
Triclinic, P1	Dx = 1.448 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.058 (5) Å	Cell parameters from 6198 reflections
b = 12.300 (5) Å	θ = 3.0–27.5°
c = 13.500 (5) Å	µ = 0.87 mm^−1
α = 90.526 (5)°	T = 293 K
β = 105.382 (5)°	Block, colourless
γ = 98.637 (5)°	0.27 × 0.24 × 0.19 mm
V = 1431.9 (11) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	6265 independent reflections
Radiation source: rotating anode	4674 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 1.6°
ω scans	h = 0→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.786, Tmax = 0.849	l = −17→16
16198 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0706P)^2] where P = (Fo^2 + 2Fc^2)/3
6265 reflections	(Δ/σ)max = 0.001
351 parameters	Δρmax = 0.65 e Å^−3
15 restraints	Δρmin = −0.60 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.82067 (3)	0.71412 (2)	0.812387 (19)	0.05643 (11)
S1	0.24990 (7)	0.64963 (6)	1.03695 (5)	0.03917 (16)
P1	0.89270 (8)	0.83242 (6)	0.68962 (5)	0.03976 (17)
O1	0.1360 (2)	0.72108 (19)	1.00246 (19)	0.0587 (6)
O2	0.2681 (3)	0.6244 (2)	1.14346 (18)	0.0603 (6)
O3	0.2255 (2)	0.55291 (18)	0.96984 (19)	0.0582 (6)
O1W	0.9384 (3)	0.5422 (2)	0.8028 (2)	0.0617 (6)
H1W1	0.868 (3)	0.497 (3)	0.819 (3)	0.092*
H1W2	1.021 (3)	0.550 (4)	0.853 (2)	0.092*
O2W	−0.0549 (18)	0.4784 (15)	0.5433 (11)	0.237 (7)	0.50
H2W1	0.0000	0.5000	0.5000	0.355*
H2W2	0.000 (12)	0.50 (2)	0.6040 (16)	0.355*	0.50
N1	0.7966 (2)	0.6867 (2)	0.97637 (19)	0.0424 (5)
H1N1	0.782 (3)	0.6141 (9)	0.979 (3)	0.064*
H1N2	0.8959 (17)	0.709 (2)	1.011 (2)	0.064*
C1	1.0808 (3)	0.8162 (2)	0.6725 (2)	0.0414 (6)
C2	1.1987 (4)	0.8086 (3)	0.7591 (2)	0.0547 (8)
H2	1.1784	0.8062	0.8231	0.066*
C3	1.3482 (4)	0.8046 (4)	0.7521 (3)	0.0700 (10)
H3	1.4282	0.8008	0.8110	0.084*
C4	1.3763 (4)	0.8063 (3)	0.6554 (3)	0.0740 (11)
H4	1.4757	0.8038	0.6496	0.089*
C5	1.2592 (4)	0.8117 (3)	0.5700 (3)	0.0697 (10)
H5	1.2786	0.8117	0.5057	0.084*
C6	1.1114 (4)	0.8171 (3)	0.5775 (2)	0.0577 (8)
H6	1.0321	0.8214	0.5183	0.069*
C7	0.7559 (3)	0.8004 (2)	0.5636 (2)	0.0455 (6)
C8	0.6856 (5)	0.6923 (3)	0.5389 (3)	0.0700 (10)
H8	0.7095	0.6390	0.5865	0.084*
C9	0.5807 (6)	0.6623 (4)	0.4452 (3)	0.0878 (13)
H9	0.5352	0.5891	0.4293	0.105*
C10	0.5433 (5)	0.7408 (4)	0.3747 (3)	0.0885 (14)
H10	0.4722	0.7206	0.3114	0.106*
C11	0.6097 (5)	0.8475 (4)	0.3974 (3)	0.0802 (12)
H11	0.5847	0.9005	0.3497	0.096*
C12	0.7160 (4)	0.8775 (3)	0.4929 (3)	0.0619 (9)
H12	0.7604	0.9509	0.5087	0.074*
C13	0.9072 (3)	0.9809 (2)	0.7080 (2)	0.0430 (6)
C14	0.7906 (4)	1.0222 (3)	0.7386 (2)	0.0559 (8)
H14	0.7072	0.9745	0.7497	0.067*
C15	0.7994 (5)	1.1354 (3)	0.7526 (3)	0.0688 (10)
H15	0.7205	1.1631	0.7719	0.083*
C16	0.9230 (5)	1.2066 (3)	0.7384 (3)	0.0706 (10)
H16	0.9284	1.2821	0.7489	0.085*
C17	1.0364 (5)	1.1670 (3)	0.7093 (3)	0.0662 (9)
H17	1.1197	1.2157	0.6994	0.079*
C18	1.0311 (4)	1.0546 (3)	0.6936 (2)	0.0542 (8)
H18	1.1105	1.0286	0.6734	0.065*
C19	0.5426 (3)	0.6758 (2)	1.0080 (2)	0.0354 (5)
H19	0.5231	0.6006	0.9914	0.043*
C20	0.4308 (3)	0.7267 (2)	1.0332 (2)	0.0367 (6)
C21	0.4580 (3)	0.8378 (2)	1.0601 (2)	0.0469 (7)
H21	0.3828	0.8716	1.0780	0.056*
C22	0.6002 (4)	0.8980 (2)	1.0597 (3)	0.0509 (7)
H22	0.6201	0.9727	1.0787	0.061*
C23	0.7131 (3)	0.8505 (2)	1.0321 (2)	0.0406 (6)
C24	0.8614 (3)	0.9190 (3)	1.0249 (3)	0.0539 (8)
H24A	0.9473	0.8967	1.0747	0.081*
H24B	0.8581	0.9953	1.0384	0.081*
H24C	0.8738	0.9089	0.9572	0.081*
C25	0.6851 (3)	0.7374 (2)	1.00730 (19)	0.0346 (5)
N2	0.5710 (4)	0.5851 (3)	0.7540 (3)	0.0848 (10)
C26	0.4561 (6)	0.5415 (4)	0.7544 (4)	0.0868 (12)
C27	0.3062 (7)	0.4811 (5)	0.7599 (5)	0.129 (2)
H27A	0.3103	0.4036	0.7603	0.194*
H27B	0.2263	0.4959	0.7012	0.194*
H27C	0.2838	0.5044	0.8217	0.194*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.06167 (17)	0.06053 (17)	0.05768 (17)	0.01306 (12)	0.03202 (12)	0.01829 (11)
S1	0.0240 (3)	0.0411 (4)	0.0537 (4)	−0.0004 (3)	0.0156 (3)	0.0031 (3)
P1	0.0409 (4)	0.0445 (4)	0.0372 (4)	0.0092 (3)	0.0149 (3)	0.0054 (3)
O1	0.0282 (10)	0.0637 (14)	0.0861 (16)	0.0109 (10)	0.0164 (10)	0.0087 (11)
O2	0.0504 (12)	0.0696 (14)	0.0584 (13)	−0.0098 (11)	0.0211 (10)	0.0121 (11)
O3	0.0404 (11)	0.0536 (13)	0.0801 (16)	−0.0093 (10)	0.0252 (11)	−0.0142 (11)
O1W	0.0545 (13)	0.0586 (14)	0.0737 (16)	0.0033 (12)	0.0234 (12)	0.0091 (12)
O2W	0.238 (10)	0.224 (9)	0.246 (10)	0.058 (8)	0.051 (8)	−0.025 (8)
N1	0.0279 (10)	0.0525 (14)	0.0506 (14)	0.0078 (10)	0.0160 (10)	0.0148 (11)
C1	0.0425 (14)	0.0416 (14)	0.0440 (15)	0.0119 (12)	0.0157 (12)	0.0043 (11)
C2	0.0546 (18)	0.068 (2)	0.0478 (17)	0.0212 (16)	0.0174 (14)	0.0113 (14)
C3	0.0513 (19)	0.094 (3)	0.067 (2)	0.0285 (19)	0.0103 (17)	0.012 (2)
C4	0.053 (2)	0.083 (3)	0.099 (3)	0.0261 (19)	0.036 (2)	0.009 (2)
C5	0.068 (2)	0.096 (3)	0.063 (2)	0.032 (2)	0.0375 (19)	0.0152 (19)
C6	0.0546 (18)	0.080 (2)	0.0454 (17)	0.0218 (17)	0.0198 (14)	0.0096 (15)
C7	0.0393 (14)	0.0556 (17)	0.0414 (15)	0.0054 (13)	0.0117 (12)	−0.0015 (13)
C8	0.083 (3)	0.058 (2)	0.062 (2)	0.0081 (19)	0.0110 (19)	−0.0077 (17)
C9	0.093 (3)	0.072 (3)	0.081 (3)	−0.003 (2)	0.002 (2)	−0.026 (2)
C10	0.072 (3)	0.115 (4)	0.064 (3)	0.021 (3)	−0.009 (2)	−0.023 (3)
C11	0.070 (3)	0.098 (3)	0.061 (2)	0.020 (2)	−0.0063 (19)	0.005 (2)
C12	0.0559 (19)	0.067 (2)	0.0537 (19)	0.0054 (17)	0.0019 (15)	0.0075 (16)
C13	0.0464 (15)	0.0482 (15)	0.0367 (14)	0.0138 (13)	0.0117 (12)	0.0029 (11)
C14	0.0483 (17)	0.067 (2)	0.0537 (18)	0.0158 (16)	0.0123 (14)	−0.0024 (15)
C15	0.077 (3)	0.074 (2)	0.061 (2)	0.039 (2)	0.0134 (18)	−0.0072 (18)
C16	0.104 (3)	0.0498 (19)	0.060 (2)	0.029 (2)	0.016 (2)	0.0022 (16)
C17	0.090 (3)	0.0454 (18)	0.065 (2)	0.0023 (18)	0.0281 (19)	0.0037 (15)
C18	0.066 (2)	0.0505 (17)	0.0548 (18)	0.0129 (16)	0.0290 (16)	0.0056 (14)
C19	0.0276 (12)	0.0347 (13)	0.0458 (14)	0.0038 (10)	0.0133 (10)	0.0070 (11)
C20	0.0246 (11)	0.0392 (14)	0.0466 (15)	0.0015 (11)	0.0120 (10)	0.0068 (11)
C21	0.0391 (14)	0.0376 (14)	0.070 (2)	0.0051 (12)	0.0261 (14)	0.0026 (13)
C22	0.0526 (17)	0.0343 (14)	0.067 (2)	−0.0023 (13)	0.0239 (15)	−0.0010 (13)
C23	0.0310 (12)	0.0440 (15)	0.0438 (14)	−0.0059 (12)	0.0114 (11)	0.0053 (11)
C24	0.0406 (15)	0.0572 (18)	0.0580 (18)	−0.0154 (14)	0.0160 (13)	0.0039 (14)
C25	0.0246 (11)	0.0429 (14)	0.0366 (13)	0.0038 (11)	0.0093 (10)	0.0099 (10)
N2	0.0546 (19)	0.095 (3)	0.094 (3)	−0.0099 (19)	0.0144 (18)	−0.002 (2)
C26	0.081 (3)	0.092 (3)	0.083 (3)	0.006 (3)	0.020 (2)	−0.009 (2)
C27	0.104 (4)	0.161 (6)	0.116 (4)	−0.044 (4)	0.055 (4)	−0.026 (4)

Geometric parameters (Å, º)

Ag1—N1	2.304 (2)	C9—H9	0.93
Ag1—P1	2.3712 (9)	C10—C11	1.355 (6)
Ag1—N2	2.491 (4)	C10—H10	0.93
Ag1—O1W	2.524 (3)	C11—C12	1.396 (5)
S1—O1	1.441 (2)	C11—H11	0.93
S1—O3	1.442 (2)	C12—H12	0.93
S1—O2	1.445 (2)	C13—C18	1.390 (4)
S1—C20	1.779 (3)	C13—C14	1.391 (4)
P1—C1	1.818 (3)	C14—C15	1.391 (5)
P1—C7	1.818 (3)	C14—H14	0.93
P1—C13	1.821 (3)	C15—C16	1.371 (6)
O1W—H1W1	0.854 (10)	C15—H15	0.93
O1W—H1W2	0.853 (10)	C16—C17	1.345 (6)
O2W—O2W^i	1.762 (17)	C16—H16	0.93
O2W—H2W1	0.881 (9)	C17—C18	1.388 (5)
O2W—H2W2	0.845 (10)	C17—H17	0.93
N1—C25	1.411 (4)	C18—H18	0.93
N1—H1N1	0.885 (10)	C19—C20	1.379 (4)
N1—H1N2	0.896 (10)	C19—C25	1.397 (3)
C1—C2	1.373 (4)	C19—H19	0.93
C1—C6	1.383 (4)	C20—C21	1.379 (4)
C2—C3	1.390 (5)	C21—C22	1.387 (4)
C2—H2	0.93	C21—H21	0.93
C3—C4	1.393 (6)	C22—C23	1.379 (4)
C3—H3	0.9300	C22—H22	0.93
C4—C5	1.353 (6)	C23—C25	1.397 (4)
C4—H4	0.93	C23—C24	1.502 (4)
C5—C6	1.380 (5)	C24—H24A	0.96
C5—H5	0.93	C24—H24B	0.96
C6—H6	0.93	C24—H24C	0.96
C7—C12	1.371 (5)	N2—C26	1.099 (6)
C7—C8	1.382 (5)	C26—C27	1.467 (7)
C8—C9	1.374 (5)	C27—H27A	0.96
C8—H8	0.93	C27—H27B	0.96
C9—C10	1.377 (7)	C27—H27C	0.96
N1—Ag1—P1	150.06 (7)	C9—C10—H10	119.9
N1—Ag1—N2	85.71 (11)	C10—C11—C12	119.6 (4)
P1—Ag1—N2	117.20 (9)	C10—C11—H11	120.2
N1—Ag1—O1W	94.06 (8)	C12—C11—H11	120.2
P1—Ag1—O1W	106.81 (6)	C7—C12—C11	121.0 (4)
N2—Ag1—O1W	83.54 (11)	C7—C12—H12	119.5
O1—S1—O3	113.35 (15)	C11—C12—H12	119.5
O1—S1—O2	112.03 (15)	C18—C13—C14	118.7 (3)
O3—S1—O2	112.98 (15)	C18—C13—P1	122.6 (2)
O1—S1—C20	106.06 (13)	C14—C13—P1	118.7 (2)
O3—S1—C20	106.33 (13)	C13—C14—C15	119.5 (3)
O2—S1—C20	105.33 (13)	C13—C14—H14	120.2
C1—P1—C7	105.53 (13)	C15—C14—H14	120.2
C1—P1—C13	103.30 (13)	C16—C15—C14	120.9 (4)
C7—P1—C13	103.75 (14)	C16—C15—H15	119.6
C1—P1—Ag1	112.36 (9)	C14—C15—H15	119.6
C7—P1—Ag1	110.54 (10)	C17—C16—C15	119.8 (3)
C13—P1—Ag1	120.07 (10)	C17—C16—H16	120.1
Ag1—O1W—H1W1	97 (3)	C15—C16—H16	120.1
Ag1—O1W—H1W2	105 (3)	C16—C17—C18	121.1 (4)
H1W1—O1W—H1W2	109 (2)	C16—C17—H17	119.5
H2W1—O2W—H2W2	109 (3)	C18—C17—H17	119.5
C25—N1—Ag1	117.66 (16)	C17—C18—C13	120.1 (3)
C25—N1—H1N1	114 (2)	C17—C18—H18	120.0
Ag1—N1—H1N1	103 (2)	C13—C18—H18	120.0
C25—N1—H1N2	116 (2)	C20—C19—C25	120.0 (2)
Ag1—N1—H1N2	98 (2)	C20—C19—H19	120.0
H1N1—N1—H1N2	105 (2)	C25—C19—H19	120.0
C2—C1—C6	119.2 (3)	C19—C20—C21	121.1 (2)
C2—C1—P1	117.8 (2)	C19—C20—S1	120.8 (2)
C6—C1—P1	123.0 (2)	C21—C20—S1	118.0 (2)
C1—C2—C3	120.7 (3)	C20—C21—C22	118.3 (3)
C1—C2—H2	119.6	C20—C21—H21	120.8
C3—C2—H2	119.6	C22—C21—H21	120.8
C2—C3—C4	119.0 (3)	C23—C22—C21	122.1 (3)
C2—C3—H3	120.5	C23—C22—H22	118.9
C4—C3—H3	120.5	C21—C22—H22	118.9
C5—C4—C3	120.2 (3)	C22—C23—C25	118.8 (2)
C5—C4—H4	119.9	C22—C23—C24	121.0 (3)
C3—C4—H4	119.9	C25—C23—C24	120.1 (3)
C4—C5—C6	120.6 (3)	C23—C24—H24A	109.5
C4—C5—H5	119.7	C23—C24—H24B	109.5
C6—C5—H5	119.7	H24A—C24—H24B	109.5
C5—C6—C1	120.3 (3)	C23—C24—H24C	109.5
C5—C6—H6	119.9	H24A—C24—H24C	109.5
C1—C6—H6	119.9	H24B—C24—H24C	109.5
C12—C7—C8	118.2 (3)	C19—C25—C23	119.5 (2)
C12—C7—P1	123.8 (2)	C19—C25—N1	120.1 (2)
C8—C7—P1	117.9 (3)	C23—C25—N1	120.2 (2)
C9—C8—C7	121.0 (4)	C26—N2—Ag1	158.9 (4)
C9—C8—H8	119.5	N2—C26—C27	177.2 (6)
C7—C8—H8	119.5	C26—C27—H27A	109.5
C8—C9—C10	119.9 (4)	C26—C27—H27B	109.5
C8—C9—H9	120.1	H27A—C27—H27B	109.5
C10—C9—H9	120.1	C26—C27—H27C	109.5
C11—C10—C9	120.3 (4)	H27A—C27—H27C	109.5
C11—C10—H10	119.9	H27B—C27—H27C	109.5

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2^ii	0.85 (1)	1.95 (1)	2.797 (3)	170 (4)
O1W—H1W2···O3^iii	0.85 (1)	2.09 (1)	2.940 (4)	174 (5)
N1—H1N2···O1^iii	0.90 (1)	2.19 (2)	2.965 (3)	144 (3)
N1—H1N1···O3^ii	0.89 (1)	2.17 (1)	3.032 (4)	164 (3)

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