Poly[(μ3-4-amino­benzene­sulfonato-κ3N:O:O)(triphenyl­phosphine-κP)silver(I)]

Sadeghi, O.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536810024207

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages m855-m856

doi:10.1107/S1600536810024207

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Poly[(μ₃-4-aminobenzenesulfonato-κ³N:O:O)(triphenylphosphine-κP)silver(I)]

Omid Sadeghi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 June 2010; accepted 22 June 2010; online 26 June 2010)

In the title 1:1 silver 4-aminobenzenesulfonate adduct with triphenylphosphine, [Ag(C₆H₆NO₃S)(C₁₈H₁₅P)]_n, the sulfonate –SO₃ unit bridges, through only one O atom, two phosphine-coordinated Ag atoms, forming a centrosymmetric Ag₂O₂ rhombus. The Ag⁺ cation adopts a considerably distorted a tetrahedral coordination. In the crystal, adjacent binuclear molecules are connected into a layer motif through the amino group of the anion; the layers are perpendicular to the a axis.

Related literature

For the synthesis of the silver reactant used in the synthesis, see: Hanna & Ng (1999 ); Ng & Othman (1997 ). For the crystal structure of 4-aminobenzenesulfonic acid, see: Banu & Golzar Hossain (2006 ); Low & Glidewell (2002 ); Rae & Maslen (1962 ). For literature on silver 4-aminobenzenesulfonate, see: Léon (1945 , 1992 ); Pan et al. (2003 ); Schreuer (1999 ). For other metal derivatives, see: Brodersen & Beck (2004 ); Li et al. (2006 ); Liu, Ma & Yang (2007 ); Liu, Wu et al. (2007 ); Ou et al. (2008 ); Wu et al. (2008 ); Zheng et al. (2002 ). For a review on metal sulfonates, see: Cai (2004 ).

Experimental

Crystal data

[Ag(C₆H₆NO₃S)(C₁₈H₁₅P)]
M_r = 542.32
Monoclinic, C 2/c
a = 28.2593 (15) Å
b = 9.4085 (5) Å
c = 18.5765 (10) Å
β = 118.229 (1)°
V = 4351.6 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.695, T_max = 0.946
19921 measured reflections
4995 independent reflections
4393 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.073
S = 1.02
4995 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.93 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—P1	2.3614 (6)
Ag1—O1	2.4252 (15)
Ag1—O1ⁱ	2.5031 (16)
Ag1—N1ⁱⁱ	2.3749 (18)

P1—Ag1—O1	131.56 (4)
P1—Ag1—O1ⁱ	124.03 (4)
P1—Ag1—N1ⁱⁱ	132.96 (5)
O1—Ag1—O1ⁱ	80.21 (5)
O1—Ag1—N1ⁱⁱ	78.12 (6)
O1ⁱ—Ag1—N1ⁱⁱ	92.43 (6)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ) and OLEX (Dolomanov et al., 2003 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024207/su2190sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024207/su2190Isup2.hkl

checkCIF report

Comment top

The crystal structure of silver 4-aminobenzenesulfonate, sulfargenta, a chemical whose ability to disinfect contaminated water was reported in 1945 (Léon, 1945; 1992), features a polymeric ribbon structure in which the nitrogen and three oxygen atoms are all involved in coordinating to silver centers (Schreuer, 1999; Pan et al., 2003). The 4-aminobenzenesulfonate ion has been studied in other metal salts; the sulfonate part of the ion exhibits diverse coordination modes, as summarized in a review of metal arenesulfonates (Cai, 2004).

Introducing a monodentate ligand such as triphenylphosphine to silver 4-aminobenzenesulfonate should lower the dimensionality (i.e., the adduct should exist as a monomeric molecule) following the suggestion of lowering the dimensionality of the related metal carboxylates by the use of bidentate N-heterocycles. However, the hexamethyleneteramine adduct has a layer structure in which only the hexamethylenetetramine ligand participates in µ₃-bridging (Zheng et al., 2002); the 1,1'-(1,4-butanediyl)-bis(imidazole) adduct similarly features an uncoordinated 4-aminobenzesulfonate group (Li et al., 2006). Other bidentate N-heterocycles result in silver 4-aminobenzenesulfonate adducts displaying chain or ladder motifs (Liu Ma & Yang, 2007; Liu, Wy et al., 2007; Wu et al., 2008). In the present study, the donor ligand is triphenylphosphine.

In the title 1:1 adduct with triphenylphosphine the sulfonate –SO₃ group bridges, through only one oxygen atom, two phosphine-coordinated silver atoms to furnish a centrosymmetric Ag₂O₂ rhombus (Fig. 1). The silver atom has a tetrahedral geometry as seen from the selected bond distances and angles involving atom Ag1, given in Table 1. In the –SO₃ portion, one bond is distinctly longer than the other two [1.489 (2) Å compared to 1.444 (2) and 1.457 (2) Å]; the oxygen atom involved in the longer bond is that which bridges the two silver atoms. Sulfanilic acid itself exists as a zwitterion but the longest bond is only slightly longer than the other two [1.476 (1) Å compared to 1.445 (1), and 1.457 (1) Å] (Low & Glidewell, 2002). On the other hand, the bonds are more symmetrical in the two modifications of the monohydrated acid (Banu et al., 2006; Rae & Maslen, 1962).

In the crystal structures of metal 4-aminobenzesulfonates (without other ligands) for which the anion is coordinated to the metal, the amino group is not usually involved in additional coordination. The exceptions are limited to silver (Schreuer, 1999; Pan et al., 2003) and mercury (Brodersen & Beck, 2004) derivatives only. In the crystal structute of the title compound adjacent [Ag(C₆H₆NO₃S)(C₁₈H₁₅P)]₂ dimers are connected into a layer motif through the amino moiety. The layers are perpendicular to the a-axis of the monoclinic unit cell (Fig. 2), with the aromatic rings of the phosphine ligand protruding into the space between the layers.

Related literature top

For the synthesis of the silver reactant used in the synthesis, see: Hanna & Ng (1999); Ng & Othman (1997). For the crystal structure of 4-aminobenzenesulfonic acid, see: Banu & Golzar Hossain (2006); Low & Glidewell (2002); Rae & Maslen (1962). For literature on silver 4-aminobenzenesulfonate, see: Léon (1945, 1992); Pan et al. (2003); Schreuer (1999). For other metal derivatives, see: Brodersen & Beck (2004); Li et al. (2006); Liu, Ma & Yang (2007); Liu, Wu et al. (2007); Ou et al. (2008); Wu et al. (2008); Zheng et al. (2002). For a review on metal sulfonanates, see: Cai (2004).

Experimental top

Silver acetate (1 mmol, 0.17 g) and triphenylphosphine (2 mmol, 0.53 g) were heated in ethanol (50 ml) until the reactants dissolved completely. Gray insoluble material was removed by filtration and the solvent removed to yield bis(silver acetate^.2triphenylphosphine) monohydrate sesquiethanol (Hanna & Ng, 1999; Ng & Othman, 1997). The adduct (0.5 mmol, 0.69 g) and 4-aminobenzenesulfonic acid (1 mmol, 0.17 g) were placed in a convection tube; the tube was filled with methanol and kept at 343 K. Colorless crystals were collected after 3 days (m.p. > 573 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of a portion of the asymmetric unit of the two-dimensional network structure of the title compound; ellipsoids are drawn at the 70% probability level and H atoms are of arbitrary radius. Symmetry transformation: (i) = 1 - x, 1 - y, 1 - z; (ii) = 3/2 - x, y - 1/2, 3/2 - z.
	Fig. 2. OLEX (Dolomanov et al., 2003) representation of the layer motif in the crystal structure of the title compound.

Poly[(µ₃-4-aminobenzenesulfonato- κ³N:O:O)(triphenylphosphine-κP)silver(I)] top

Crystal data top

[Ag(C₆H₆NO₃S)(C₁₈H₁₅P)]	F(000) = 2192
M_r = 542.32	D_x = 1.656 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8286 reflections
a = 28.2593 (15) Å	θ = 2.4–28.2°
b = 9.4085 (5) Å	µ = 1.12 mm⁻¹
c = 18.5765 (10) Å	T = 100 K
β = 118.229 (1)°	Plate, colorless
V = 4351.6 (4) Å³	0.35 × 0.30 × 0.05 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	4995 independent reflections
Radiation source: fine-focus sealed tube	4393 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→36
T_min = 0.695, T_max = 0.946	k = −11→12
19921 measured reflections	l = −24→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0414P)² + 3.5194P] where P = (F_o² + 2F_c²)/3
4995 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.93 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Ag(C₆H₆NO₃S)(C₁₈H₁₅P)]	V = 4351.6 (4) Å³
M_r = 542.32	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.2593 (15) Å	µ = 1.12 mm⁻¹
b = 9.4085 (5) Å	T = 100 K
c = 18.5765 (10) Å	0.35 × 0.30 × 0.05 mm
β = 118.229 (1)°

Data collection top

Bruker SMART APEX diffractometer	4995 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4393 reflections with I > 2σ(I)
T_min = 0.695, T_max = 0.946	R_int = 0.038
19921 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.02	Δρ_max = 0.93 e Å⁻³
4995 reflections	Δρ_min = −0.46 e Å⁻³
280 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.692581 (6)	0.726456 (18)	0.523729 (10)	0.01618 (6)
S1	0.80640 (2)	0.94131 (6)	0.63130 (3)	0.01479 (11)
P1	0.61400 (2)	0.83696 (6)	0.51114 (3)	0.01347 (12)
O1	0.78580 (6)	0.80116 (17)	0.59157 (9)	0.0175 (3)
O2	0.86414 (6)	0.94896 (18)	0.66660 (10)	0.0215 (3)
O3	0.77760 (6)	1.05818 (17)	0.57660 (9)	0.0199 (3)
N1	0.76252 (7)	1.0121 (2)	0.91345 (11)	0.0172 (4)
H1A	0.7749	0.9431	0.9478	0.021*
H1B	0.7287	1.0201	0.8978	0.021*
C1	0.55223 (9)	0.7331 (2)	0.45987 (14)	0.0152 (4)
C2	0.54236 (9)	0.6587 (3)	0.38905 (15)	0.0241 (5)
H2	0.5675	0.6618	0.3687	0.029*
C3	0.49531 (10)	0.5800 (3)	0.34867 (16)	0.0283 (6)
H3	0.4881	0.5313	0.2998	0.034*
C4	0.45886 (9)	0.5712 (2)	0.37823 (15)	0.0236 (5)
H4	0.4272	0.5157	0.3504	0.028*
C5	0.46888 (9)	0.6441 (2)	0.44884 (15)	0.0211 (5)
H5	0.4440	0.6386	0.4697	0.025*
C6	0.51523 (9)	0.7254 (2)	0.48923 (14)	0.0171 (4)
H6	0.5217	0.7761	0.5373	0.021*
C7	0.59882 (8)	1.0046 (2)	0.45534 (12)	0.0149 (4)
C8	0.54666 (9)	1.0490 (2)	0.40320 (13)	0.0189 (4)
H8	0.5172	0.9886	0.3932	0.023*
C9	0.53739 (10)	1.1817 (3)	0.36545 (15)	0.0235 (5)
H9	0.5017	1.2115	0.3298	0.028*
C10	0.58010 (10)	1.2702 (2)	0.37993 (15)	0.0228 (5)
H10	0.5737	1.3612	0.3548	0.027*
C11	0.63252 (10)	1.2255 (2)	0.43143 (14)	0.0216 (5)
H11	0.6619	1.2859	0.4410	0.026*
C12	0.64191 (9)	1.0932 (2)	0.46869 (13)	0.0186 (4)
H12	0.6777	1.0627	0.5033	0.022*
C13	0.61624 (8)	0.8853 (2)	0.60765 (12)	0.0141 (4)
C14	0.63746 (9)	0.7881 (2)	0.67208 (14)	0.0184 (5)
H14	0.6528	0.7019	0.6663	0.022*
C15	0.63632 (9)	0.8164 (3)	0.74441 (14)	0.0214 (5)
H15	0.6501	0.7488	0.7875	0.026*
C16	0.61496 (9)	0.9438 (2)	0.75397 (14)	0.0197 (5)
H16	0.6141	0.9630	0.8036	0.024*
C17	0.59487 (8)	1.0430 (2)	0.69125 (13)	0.0171 (4)
H17	0.5807	1.1305	0.6981	0.021*
C18	0.59550 (8)	1.0140 (2)	0.61829 (13)	0.0157 (4)
H18	0.5818	1.0821	0.5754	0.019*
C19	0.79126 (8)	0.9533 (2)	0.71350 (12)	0.0132 (4)
C20	0.82240 (8)	0.8805 (2)	0.78608 (13)	0.0154 (4)
H20	0.8507	0.8203	0.7906	0.019*
C21	0.81224 (8)	0.8956 (2)	0.85197 (13)	0.0157 (4)
H21	0.8335	0.8457	0.9014	0.019*
C22	0.77081 (8)	0.9840 (2)	0.84538 (12)	0.0144 (4)
C23	0.73961 (8)	1.0556 (2)	0.77244 (13)	0.0166 (4)
H23	0.7112	1.1154	0.7677	0.020*
C24	0.74968 (8)	1.0406 (2)	0.70679 (13)	0.0157 (4)
H24	0.7282	1.0899	0.6572	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01579 (9)	0.01658 (10)	0.01879 (10)	0.00209 (6)	0.01033 (7)	0.00064 (6)
S1	0.0160 (2)	0.0163 (3)	0.0144 (2)	−0.00364 (19)	0.0091 (2)	−0.00339 (19)
P1	0.0141 (2)	0.0126 (3)	0.0154 (3)	0.00022 (19)	0.0084 (2)	0.0003 (2)
O1	0.0188 (7)	0.0178 (8)	0.0184 (8)	−0.0042 (6)	0.0110 (6)	−0.0062 (6)
O2	0.0177 (7)	0.0275 (9)	0.0218 (8)	−0.0059 (6)	0.0114 (6)	−0.0070 (7)
O3	0.0261 (8)	0.0192 (8)	0.0166 (7)	−0.0013 (6)	0.0120 (7)	0.0006 (6)
N1	0.0208 (9)	0.0170 (9)	0.0163 (9)	−0.0019 (7)	0.0109 (7)	−0.0007 (7)
C1	0.0157 (10)	0.0099 (10)	0.0192 (11)	0.0017 (7)	0.0077 (8)	0.0023 (8)
C2	0.0212 (11)	0.0267 (13)	0.0279 (12)	−0.0021 (9)	0.0143 (10)	−0.0087 (10)
C3	0.0255 (12)	0.0268 (14)	0.0290 (13)	−0.0015 (10)	0.0100 (10)	−0.0119 (10)
C4	0.0178 (10)	0.0139 (11)	0.0320 (13)	−0.0007 (8)	0.0060 (9)	0.0003 (9)
C5	0.0182 (10)	0.0173 (12)	0.0293 (12)	0.0006 (8)	0.0124 (9)	0.0052 (9)
C6	0.0178 (10)	0.0153 (11)	0.0179 (11)	0.0014 (8)	0.0082 (9)	0.0018 (8)
C7	0.0204 (10)	0.0133 (10)	0.0145 (9)	−0.0003 (8)	0.0111 (8)	0.0003 (8)
C8	0.0203 (10)	0.0191 (11)	0.0209 (11)	0.0001 (9)	0.0127 (9)	0.0022 (9)
C9	0.0269 (12)	0.0229 (12)	0.0240 (12)	0.0071 (10)	0.0149 (10)	0.0065 (10)
C10	0.0375 (14)	0.0138 (11)	0.0237 (12)	0.0019 (9)	0.0200 (11)	0.0027 (9)
C11	0.0314 (12)	0.0191 (12)	0.0190 (11)	−0.0083 (9)	0.0157 (10)	−0.0046 (9)
C12	0.0212 (10)	0.0196 (11)	0.0166 (10)	−0.0043 (9)	0.0101 (9)	−0.0023 (9)
C13	0.0134 (9)	0.0157 (11)	0.0136 (9)	−0.0005 (8)	0.0067 (8)	−0.0005 (8)
C14	0.0229 (11)	0.0126 (11)	0.0208 (11)	0.0035 (8)	0.0113 (9)	0.0029 (8)
C15	0.0288 (12)	0.0162 (11)	0.0213 (11)	0.0046 (9)	0.0136 (10)	0.0052 (9)
C16	0.0234 (11)	0.0201 (12)	0.0188 (10)	−0.0014 (9)	0.0125 (9)	−0.0015 (9)
C17	0.0182 (10)	0.0129 (10)	0.0229 (11)	−0.0006 (8)	0.0119 (9)	−0.0020 (8)
C18	0.0151 (9)	0.0124 (10)	0.0190 (10)	0.0003 (8)	0.0076 (8)	0.0025 (8)
C19	0.0165 (9)	0.0121 (10)	0.0130 (9)	−0.0030 (8)	0.0086 (8)	−0.0036 (8)
C20	0.0159 (9)	0.0124 (10)	0.0180 (10)	0.0005 (8)	0.0080 (8)	−0.0015 (8)
C21	0.0179 (10)	0.0125 (10)	0.0144 (10)	0.0001 (8)	0.0059 (8)	0.0006 (8)
C22	0.0164 (9)	0.0129 (10)	0.0147 (9)	−0.0043 (8)	0.0080 (8)	−0.0013 (8)
C23	0.0156 (9)	0.0169 (11)	0.0188 (10)	0.0017 (8)	0.0095 (8)	−0.0022 (8)
C24	0.0176 (10)	0.0141 (10)	0.0142 (10)	0.0008 (8)	0.0065 (8)	0.0009 (8)

Geometric parameters (Å, º) top

Ag1—P1	2.3614 (6)	C8—H8	0.9500
Ag1—O1	2.4252 (15)	C9—C10	1.384 (4)
Ag1—O1ⁱ	2.5031 (16)	C9—H9	0.9500
Ag1—N1ⁱⁱ	2.3749 (18)	C10—C11	1.395 (4)
S1—O2	1.4441 (15)	C10—H10	0.9500
S1—O3	1.4565 (17)	C11—C12	1.388 (3)
S1—O1	1.4885 (16)	C11—H11	0.9500
S1—C19	1.774 (2)	C12—H12	0.9500
P1—C13	1.821 (2)	C13—C14	1.396 (3)
P1—C7	1.824 (2)	C13—C18	1.400 (3)
P1—C1	1.826 (2)	C14—C15	1.385 (3)
O1—Ag1ⁱ	2.5031 (16)	C14—H14	0.9500
N1—C22	1.416 (3)	C15—C16	1.391 (3)
N1—Ag1ⁱⁱⁱ	2.3749 (18)	C15—H15	0.9500
N1—H1A	0.8600	C16—C17	1.387 (3)
N1—H1B	0.8600	C16—H16	0.9500
C1—C6	1.391 (3)	C17—C18	1.391 (3)
C1—C2	1.397 (3)	C17—H17	0.9500
C2—C3	1.391 (3)	C18—H18	0.9500
C2—H2	0.9500	C19—C24	1.390 (3)
C3—C4	1.380 (4)	C19—C20	1.393 (3)
C3—H3	0.9500	C20—C21	1.390 (3)
C4—C5	1.385 (3)	C20—H20	0.9500
C4—H4	0.9500	C21—C22	1.394 (3)
C5—C6	1.391 (3)	C21—H21	0.9500
C5—H5	0.9500	C22—C23	1.392 (3)
C6—H6	0.9500	C23—C24	1.384 (3)
C7—C8	1.391 (3)	C23—H23	0.9500
C7—C12	1.398 (3)	C24—H24	0.9500
C8—C9	1.395 (3)

P1—Ag1—O1	131.56 (4)	C9—C8—H8	119.9
P1—Ag1—O1ⁱ	124.03 (4)	C10—C9—C8	120.1 (2)
P1—Ag1—N1ⁱⁱ	132.96 (5)	C10—C9—H9	119.9
O1—Ag1—O1ⁱ	80.21 (5)	C8—C9—H9	119.9
O1—Ag1—N1ⁱⁱ	78.12 (6)	C9—C10—C11	119.9 (2)
O1ⁱ—Ag1—N1ⁱⁱ	92.43 (6)	C9—C10—H10	120.1
O2—S1—O3	114.68 (10)	C11—C10—H10	120.1
O2—S1—O1	111.23 (9)	C12—C11—C10	120.2 (2)
O3—S1—O1	111.38 (9)	C12—C11—H11	119.9
O2—S1—C19	106.66 (9)	C10—C11—H11	119.9
O3—S1—C19	105.65 (10)	C11—C12—C7	120.1 (2)
O1—S1—C19	106.65 (9)	C11—C12—H12	120.0
C13—P1—C7	103.46 (10)	C7—C12—H12	120.0
C13—P1—C1	103.10 (10)	C14—C13—C18	119.0 (2)
C7—P1—C1	104.85 (10)	C14—C13—P1	118.77 (17)
C13—P1—Ag1	114.78 (7)	C18—C13—P1	122.22 (16)
C7—P1—Ag1	113.23 (7)	C15—C14—C13	120.6 (2)
C1—P1—Ag1	115.99 (7)	C15—C14—H14	119.7
S1—O1—Ag1	126.03 (9)	C13—C14—H14	119.7
S1—O1—Ag1ⁱ	108.65 (8)	C14—C15—C16	120.0 (2)
Ag1—O1—Ag1ⁱ	99.79 (5)	C14—C15—H15	120.0
C22—N1—Ag1ⁱⁱⁱ	108.76 (13)	C16—C15—H15	120.0
C22—N1—H1A	109.9	C17—C16—C15	120.1 (2)
Ag1ⁱⁱⁱ—N1—H1A	109.9	C17—C16—H16	119.9
C22—N1—H1B	109.9	C15—C16—H16	119.9
Ag1ⁱⁱⁱ—N1—H1B	109.9	C16—C17—C18	119.9 (2)
H1A—N1—H1B	108.3	C16—C17—H17	120.1
C6—C1—C2	119.4 (2)	C18—C17—H17	120.1
C6—C1—P1	122.24 (17)	C17—C18—C13	120.4 (2)
C2—C1—P1	118.36 (18)	C17—C18—H18	119.8
C3—C2—C1	119.3 (2)	C13—C18—H18	119.8
C3—C2—H2	120.4	C24—C19—C20	119.86 (19)
C1—C2—H2	120.4	C24—C19—S1	119.90 (16)
C4—C3—C2	121.3 (2)	C20—C19—S1	120.19 (16)
C4—C3—H3	119.3	C19—C20—C21	120.20 (19)
C2—C3—H3	119.3	C19—C20—H20	119.9
C3—C4—C5	119.3 (2)	C21—C20—H20	119.9
C3—C4—H4	120.3	C20—C21—C22	119.88 (19)
C5—C4—H4	120.3	C20—C21—H21	120.1
C4—C5—C6	120.1 (2)	C22—C21—H21	120.1
C4—C5—H5	119.9	C23—C22—C21	119.58 (19)
C6—C5—H5	119.9	C23—C22—N1	118.87 (19)
C1—C6—C5	120.5 (2)	C21—C22—N1	121.33 (19)
C1—C6—H6	119.7	C24—C23—C22	120.57 (19)
C5—C6—H6	119.7	C24—C23—H23	119.7
C8—C7—C12	119.5 (2)	C22—C23—H23	119.7
C8—C7—P1	122.84 (17)	C23—C24—C19	119.91 (19)
C12—C7—P1	117.63 (16)	C23—C24—H24	120.0
C7—C8—C9	120.3 (2)	C19—C24—H24	120.0
C7—C8—H8	119.9

N1ⁱⁱ—Ag1—P1—C13	61.30 (10)	C12—C7—C8—C9	−0.9 (3)
O1—Ag1—P1—C13	−55.43 (10)	P1—C7—C8—C9	176.62 (18)
O1ⁱ—Ag1—P1—C13	−164.36 (9)	C7—C8—C9—C10	−0.2 (4)
N1ⁱⁱ—Ag1—P1—C7	179.81 (10)	C8—C9—C10—C11	0.9 (4)
O1—Ag1—P1—C7	63.08 (9)	C9—C10—C11—C12	−0.5 (4)
O1ⁱ—Ag1—P1—C7	−45.86 (9)	C10—C11—C12—C7	−0.6 (3)
N1ⁱⁱ—Ag1—P1—C1	−58.88 (10)	C8—C7—C12—C11	1.3 (3)
O1—Ag1—P1—C1	−175.61 (9)	P1—C7—C12—C11	−176.36 (17)
O1ⁱ—Ag1—P1—C1	75.45 (9)	C7—P1—C13—C14	−167.37 (17)
O2—S1—O1—Ag1	179.26 (10)	C1—P1—C13—C14	83.59 (18)
O3—S1—O1—Ag1	−51.46 (13)	Ag1—P1—C13—C14	−43.50 (19)
C19—S1—O1—Ag1	63.33 (13)	C7—P1—C13—C18	15.24 (19)
O2—S1—O1—Ag1ⁱ	−62.88 (11)	C1—P1—C13—C18	−93.81 (18)
O3—S1—O1—Ag1ⁱ	66.41 (10)	Ag1—P1—C13—C18	139.11 (15)
C19—S1—O1—Ag1ⁱ	−178.80 (8)	C18—C13—C14—C15	2.2 (3)
P1—Ag1—O1—S1	−5.52 (14)	P1—C13—C14—C15	−175.26 (18)
N1ⁱⁱ—Ag1—O1—S1	−143.61 (12)	C13—C14—C15—C16	−1.4 (4)
O1ⁱ—Ag1—O1—S1	121.79 (13)	C14—C15—C16—C17	−0.1 (4)
P1—Ag1—O1—Ag1ⁱ	−127.30 (4)	C15—C16—C17—C18	0.8 (3)
N1ⁱⁱ—Ag1—O1—Ag1ⁱ	94.60 (6)	C16—C17—C18—C13	0.1 (3)
O1ⁱ—Ag1—O1—Ag1ⁱ	0.0	C14—C13—C18—C17	−1.6 (3)
C13—P1—C1—C6	10.1 (2)	P1—C13—C18—C17	175.83 (16)
C7—P1—C1—C6	−97.93 (19)	O2—S1—C19—C24	135.67 (17)
Ag1—P1—C1—C6	136.39 (16)	O3—S1—C19—C24	13.22 (19)
C13—P1—C1—C2	−169.57 (18)	O1—S1—C19—C24	−105.38 (18)
C7—P1—C1—C2	82.43 (19)	O2—S1—C19—C20	−41.5 (2)
Ag1—P1—C1—C2	−43.2 (2)	O3—S1—C19—C20	−163.96 (17)
C6—C1—C2—C3	0.9 (4)	O1—S1—C19—C20	77.43 (18)
P1—C1—C2—C3	−179.43 (19)	C24—C19—C20—C21	−0.4 (3)
C1—C2—C3—C4	−1.6 (4)	S1—C19—C20—C21	176.75 (16)
C2—C3—C4—C5	1.1 (4)	C19—C20—C21—C22	−0.1 (3)
C3—C4—C5—C6	0.1 (3)	C20—C21—C22—C23	0.6 (3)
C2—C1—C6—C5	0.2 (3)	C20—C21—C22—N1	−174.11 (19)
P1—C1—C6—C5	−179.41 (17)	Ag1ⁱⁱⁱ—N1—C22—C23	−80.1 (2)
C4—C5—C6—C1	−0.8 (3)	Ag1ⁱⁱⁱ—N1—C22—C21	94.6 (2)
C13—P1—C7—C8	−91.2 (2)	C21—C22—C23—C24	−0.5 (3)
C1—P1—C7—C8	16.6 (2)	N1—C22—C23—C24	174.28 (19)
Ag1—P1—C7—C8	143.97 (17)	C22—C23—C24—C19	0.0 (3)
C13—P1—C7—C12	86.45 (18)	C20—C19—C24—C23	0.5 (3)
C1—P1—C7—C12	−165.81 (17)	S1—C19—C24—C23	−176.71 (17)
Ag1—P1—C7—C12	−38.43 (19)

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

Experimental details

Crystal data
Chemical formula	[Ag(C₆H₆NO₃S)(C₁₈H₁₅P)]
M_r	542.32
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	28.2593 (15), 9.4085 (5), 18.5765 (10)
β (°)	118.229 (1)
V (Å³)	4351.6 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.35 × 0.30 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.695, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	19921, 4995, 4393
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.02
No. of reflections	4995
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.93, −0.46

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Ag1—P1	2.3614 (6)	Ag1—O1ⁱ	2.5031 (16)
Ag1—O1	2.4252 (15)	Ag1—N1ⁱⁱ	2.3749 (18)

P1—Ag1—O1	131.56 (4)	O1—Ag1—O1ⁱ	80.21 (5)
P1—Ag1—O1ⁱ	124.03 (4)	O1—Ag1—N1ⁱⁱ	78.12 (6)
P1—Ag1—N1ⁱⁱ	132.96 (5)	O1ⁱ—Ag1—N1ⁱⁱ	92.43 (6)

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

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Banu, A. & Golzar Hossain, G. M. (2006). Acta Cryst. E62, o2252–o2253. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Brodersen, K. & Beck, R. (2004). Z. Anorg. Allg. Chem. 553, 35–49. CSD CrossRef Web of Science Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, J. (2004). Coord. Chem. Rev. 248, 1061–1083. Web of Science CSD CrossRef CAS Google Scholar
Dolomanov, O. V., Blake, A. J., Champness, N. R. & Schröder, M. (2003). J. Appl. Cryst. 36, 1283–1284. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hanna, J. V. & Ng, S. W. (1999). Acta Cryst. C55 IUC9900031. Google Scholar
Léon, A. P. (1945). Rev. Inst. Salubridad Enfermedades Trop. (Mex.), 6, 123–130. Google Scholar
Léon, A. (1992). 50 Años De Investigación en México (Fifty Years of Research in Mexico), 782 pp. Centro de Documentación Institucional, História Natural das Doenças México, Mexico. Google Scholar
Li, F.-F., Ma, J.-F., Song, S.-Y., Yang, J., Jia, H.-Q. & Hu, N.-H. (2006). Cryst. Growth Des. 6, 209–215. Web of Science CSD CrossRef CAS Google Scholar
Liu, H.-Y., Ma, J.-C. & Yang, J. (2007). Acta Cryst. E63, m2707. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, H.-Y., Wu, H., Ma, J.-F., Song, S.-Y., Yang, J., Liu, Y.-Y. & Su, Z.-M. (2007). Inorg. Chem. 46, 7299–7311. Web of Science CSD CrossRef PubMed CAS Google Scholar
Low, J. N. & Glidewell, C. (2002). Acta Cryst. C58, o209–o211. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ng, S. W. & Othman, A. H. (1997). Acta Cryst. C53, 1396–1400. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Ou, G.-C., Zhang, M., Yuan, X.-Y. & Dai, Y.-Q. (2008). Acta Cryst. E64, m1587. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pan, Y.-J., Meng, F.-J., Wang, X.-J., Zhu, H.-L. & Wang, D.-Q. (2003). Z. Kristallogr. New Cryst. Struct. 218, 253–254. CAS Google Scholar
Rae, A. I. M. & Maslen, E. N. (1962). Acta Cryst. 15, 1285–1291. CSD CrossRef IUCr Journals Web of Science Google Scholar
Schreuer, J. (1999). Z. Kristallogr. New Cryst. Struct. 214, 311–312. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar
Wu, H., Dong, X.-W., Liu, H.-Y., Ma, J.-F., Li, S.-L., Yang, J., Liu, Y.-Y. & Su, Z.-M. (2008). Dalton Trans. pp. 5331–5341. Web of Science CSD CrossRef Google Scholar
Zheng, S. L., Tong, M.-L., Chen, X.-M. & Ng, S. W. (2002). J. Chem. Soc. Dalton Trans. pp. 360–364. Web of Science CSD CrossRef Google Scholar