Poly[(μ(3)-4-amino-benzene-sulfonato-κN:O:O)(triphenyl-phosphine-κP)silver(I)].

In the title 1:1 silver 4-amino-benzene-sulfonate adduct with triphenyl-phosphine, [Ag(C(6)H(6)NO(3)S)(C(18)H(15)P)](n), the sulfon-ate -SO(3) unit bridges, through only one O atom, two phosphine-coordinated Ag atoms, forming a centrosymmetric Ag(2)O(2) rhombus. The Ag(+) cation adopts a considerably distorted a tetra-hedral coordination. In the crystal, adjacent binuclear mol-ecules 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 = 542.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.02

4995 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.93 e Å−3

Δρmin = −0.46 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag(C6H6NO3S)(C18H15P)]	F(000) = 2192
Mr = 542.32	Dx = 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

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

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(Fo2) + (0.0414P)2 + 3.5194P] where P = (Fo2 + 2Fc2)/3
4995 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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) ; (ii) .