Aqua­(trifluoro­methane­sulfonato)­bis­(1,3,7-trimethyl­purine-2,6-dione)silver(I)

Arman, H.D.; Miller, T.; Tiekink, E.R.T.

doi:10.1107/S1600536810035300

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1211

doi:10.1107/S1600536810035300

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Aqua(trifluoromethanesulfonato)bis(1,3,7-trimethylpurine-2,6-dione)silver(I)

Hadi D. Arman,^a Tyler Miller ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 27 August 2010; accepted 1 September 2010; online 4 September 2010)

In the title compound, [Ag(CF₃SO₃)(C₈H₁₀N₄O₂)₂(H₂O)], the Ag^I atom is coordinated by two caffeine N atoms and, at longer distances, two O atoms of a coordinated water molecule and the trifluoromethanesulfonate anion, resulting in an AgN₂O₂ seesaw geometry. The caffeine molecules are roughly coplanar [dihedral angle = 5.81 (5)°]. In the crystal, molecules self-assemble into a linear supramolecular chain along the c axis via O—H⋯O hydrogen bonds involving the coordinated water moledcule and carbonyl O atoms. The packing is consolidated by weak C—H⋯O interactions.

Related literature

For structural diversity in the supramolecular structures of silver salts, see: Kundu et al. (2010 ). For a related Ag structure, see: Arman et al. (2010 ).

Experimental

Crystal data

[Ag(CF₃SO₃)(C₈H₁₀N₄O₂)₂(H₂O)]
M_r = 663.36
Triclinic, $[P \overline 1]$
a = 8.9012 (10) Å
b = 10.0408 (8) Å
c = 15.457 (2) Å
α = 72.091 (7)°
β = 85.444 (9)°
γ = 63.672 (6)°
V = 1175.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 98 K
0.42 × 0.27 × 0.10 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.568, T_max = 1
7271 measured reflections
5323 independent reflections
5140 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.14
5323 reflections
355 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag—N7	2.213 (2)
Ag—N3	2.218 (2)
Ag—O1w	2.4347 (19)
Ag—O7	2.5591 (19)

N7—Ag—N3	165.48 (8)
N7—Ag—O1w	98.70 (8)
N3—Ag—O1w	95.81 (7)
N7—Ag—O7	90.01 (7)
N3—Ag—O7	88.93 (7)
O1w—Ag—O7	92.39 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯O1ⁱ	0.84	1.89	2.724 (3)	170
O1w—H2w⋯O3ⁱⁱ	0.84	1.89	2.701 (3)	163
C10—H10c⋯O1wⁱⁱ	0.98	2.55	3.428 (4)	149
C15—H15c⋯O4ⁱⁱ	0.98	2.60	3.382 (4)	137
C4—H4b⋯O6ⁱⁱⁱ	0.98	2.41	3.252 (4)	144
C12—H12c⋯O5ⁱⁱⁱ	0.98	2.36	3.278 (4)	155
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) x-1, y+1, z.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035300/hb5627sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035300/hb5627Isup2.hkl

checkCIF report

Comment top

As a continuation of recent structural studies on silver salts (Arman et al., 2010), of fascination owing to the structural diversity of their supramolecular structures (Kundu et al., 2010), the title compound, (I), was isolated and characterized.

The Ag atom in (I) is coordinated by a water molecule, two N atoms derived from two caffeine molecules and an O atom from the trifluoromethanesulfonate anion, Fig. 1. While the Ag—N bond distances are experimentally equivalent, they are shorter than the Ag—O(water) and even longer Ag—O(trifluoromethanesulfonate) distances, Table 1. Reflecting the disparity in the Ag—X bond distances, the N₂O₂ coordination geometry is highly distorted tetrahedral owing to the dominanace of the Ag—N bonds that are almost diagonally opposite [N3—Ag—N7 = 165.48 (8) °]. Each of the N3- and N7-caffeine rings is planar [r.m.s. deviation of the 14 non-hydrogen atoms = 0.013 and 0.029 Å, respectively] and are almost co-planar as seen in the dihedral angle formed between them of 5.81 (5) °.

In the crystal packing, centrosymmetrically related molecules associate via O—H···O hydrogen bonds formed between the coordinated water molecule and carbonyl-O, Fig. 2 and Table 2. This arrangement is stabilized by C—H···O interactions involving the O1w and O4 atoms as acceptors, Table 1, and π···π [ring centroid(N1,N2,C1,C3,C5,C8)···centroid(N1,N2,C1,C3,C5,C8)ⁱ = 3.5605 (16) ° for i: 2 - x, 1 - y, 1 - z] contacts. The primary interactions linking the resulting supramolecular chains aligned along the c axis are of the type C—H···O, Fig. 3 and Table 1.

Related literature top

For structural diversity in the supramolecular structures of silver salts, see: Kundu et al. (2010). For a related Ag structure, see: Arman et al. (2010).

Experimental top

Caffeine (Analytical & Research Chemical Company, 0.015 g, 0.08 mmol) was dissolved in 5 ml of ethanol and silver trifluoromethanesulfonate (ACROS, 0.012 g, 0.04 mmol) also dissolved in 5 ml of ethanol was added to this. The resulting solution was gently heated and allowed to stand for slow evaporation, which afforded colourless blocks of (I) after 10 days; m. pt: 447–451 K. IR (cm^-1): ν(O—H) 3454, ν(C═O) 1700, ν(C═N)1549, ν(C—F) 1156, ν(S—O) 1028.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Asymmetric unit in the structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Portion of the supramolecular chain aligned along the c axis in (I). The O—H···O hydrogen bonds are shown as orange dashed lines.
	Fig. 3. A view in projection down the a axis of the crystal packing in (I). The O—H···O hydrogen bonds and C—H···O contacts are shown as orange and blue dashed lines, respectively.

Aqua(trifluoromethanesulfonato)bis(1,3,7-trimethylpurine-2,6-dione)silver(I) top

Crystal data top

[Ag(CF₃SO₃)(C₈H₁₀N₄O₂)₂(H₂O)]	Z = 2
M_r = 663.36	F(000) = 668
Triclinic, P1	D_x = 1.874 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.9012 (10) Å	Cell parameters from 3724 reflections
b = 10.0408 (8) Å	θ = 2.4–40.6°
c = 15.457 (2) Å	µ = 1.03 mm⁻¹
α = 72.091 (7)°	T = 98 K
β = 85.444 (9)°	Block, colorless
γ = 63.672 (6)°	0.42 × 0.27 × 0.10 mm
V = 1175.6 (2) Å³

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	5323 independent reflections
Radiation source: fine-focus sealed tube	5140 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
T_min = 0.568, T_max = 1	k = −13→11
7271 measured reflections	l = −20→19

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0466P)² + 1.1737P] where P = (F_o² + 2F_c²)/3
5323 reflections	(Δ/σ)_max = 0.001
355 parameters	Δρ_max = 0.63 e Å⁻³
3 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

[Ag(CF₃SO₃)(C₈H₁₀N₄O₂)₂(H₂O)]	γ = 63.672 (6)°
M_r = 663.36	V = 1175.6 (2) Å³
Triclinic, P1	Z = 2
a = 8.9012 (10) Å	Mo Kα radiation
b = 10.0408 (8) Å	µ = 1.03 mm⁻¹
c = 15.457 (2) Å	T = 98 K
α = 72.091 (7)°	0.42 × 0.27 × 0.10 mm
β = 85.444 (9)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	5323 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5140 reflections with I > 2σ(I)
T_min = 0.568, T_max = 1	R_int = 0.020
7271 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	3 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.14	Δρ_max = 0.63 e Å⁻³
5323 reflections	Δρ_min = −0.86 e Å⁻³
355 parameters

Special details top

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

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

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

	x	y	z	U_iso*/U_eq
Ag	0.92178 (2)	0.48844 (2)	0.188475 (12)	0.01653 (8)
S1	1.24387 (8)	0.07772 (7)	0.21533 (4)	0.01613 (13)
F1	1.1161 (2)	−0.1212 (2)	0.27088 (15)	0.0355 (4)
F2	1.3860 (2)	−0.2279 (2)	0.27639 (14)	0.0331 (4)
F3	1.2548 (3)	−0.1155 (2)	0.37600 (12)	0.0356 (4)
O1	1.2942 (2)	0.5290 (2)	0.54121 (13)	0.0215 (4)
O2	0.7737 (3)	0.9110 (2)	0.41597 (14)	0.0233 (4)
O3	0.5572 (2)	0.5224 (2)	−0.19291 (13)	0.0217 (4)
O4	0.3195 (2)	0.9238 (2)	−0.06788 (13)	0.0200 (4)
O1w	0.6921 (2)	0.4768 (3)	0.28220 (13)	0.0225 (4)
H1w	0.6922	0.4669	0.3382	0.034*
H2w	0.6035	0.4812	0.2635	0.034*
O5	1.2439 (3)	0.0652 (3)	0.12484 (14)	0.0292 (5)
O6	1.3918 (3)	0.0794 (2)	0.24474 (17)	0.0295 (5)
O7	1.0872 (2)	0.1910 (2)	0.23664 (13)	0.0196 (4)
N1	1.0320 (3)	0.7175 (3)	0.47948 (15)	0.0161 (4)
N2	0.9007 (3)	0.7135 (3)	0.35260 (15)	0.0160 (4)
N3	1.0696 (3)	0.4918 (3)	0.29602 (15)	0.0170 (4)
N4	1.2894 (3)	0.3795 (3)	0.39758 (15)	0.0160 (4)
N5	0.4349 (3)	0.7199 (3)	−0.12752 (15)	0.0160 (4)
N6	0.5649 (3)	0.7186 (3)	0.00204 (14)	0.0155 (4)
N7	0.8288 (3)	0.4857 (3)	0.06071 (15)	0.0172 (4)
N8	0.8324 (3)	0.3657 (3)	−0.04021 (15)	0.0166 (4)
C1	1.1779 (3)	0.5806 (3)	0.48418 (17)	0.0156 (5)
C2	1.0253 (4)	0.7989 (3)	0.54543 (18)	0.0208 (5)
H2A	1.1136	0.8343	0.5346	0.031*
H2B	1.0427	0.7275	0.6075	0.031*
H2C	0.9153	0.8892	0.5381	0.031*
C3	0.8935 (3)	0.7894 (3)	0.41529 (18)	0.0169 (5)
C4	0.7618 (3)	0.7835 (3)	0.28352 (19)	0.0206 (5)
H4A	0.7994	0.8207	0.2235	0.031*
H4B	0.6682	0.8714	0.2978	0.031*
H4C	0.7247	0.7052	0.2829	0.031*
C5	1.0406 (3)	0.5789 (3)	0.35362 (17)	0.0143 (5)
C6	1.2221 (3)	0.3717 (3)	0.32635 (18)	0.0168 (5)
H6	1.2761	0.2898	0.2997	0.020*
C7	1.4535 (3)	0.2678 (3)	0.44590 (19)	0.0207 (5)
H7A	1.5136	0.1906	0.4138	0.031*
H7B	1.4372	0.2147	0.5081	0.031*
H7C	1.5193	0.3234	0.4481	0.031*
C8	1.1738 (3)	0.5129 (3)	0.41647 (17)	0.0147 (5)
C9	0.5606 (3)	0.5776 (3)	−0.13270 (17)	0.0154 (5)
C10	0.2981 (3)	0.8070 (3)	−0.19966 (19)	0.0207 (5)
H10A	0.3385	0.8553	−0.2556	0.031*
H10B	0.2040	0.8883	−0.1803	0.031*
H10C	0.2605	0.7354	−0.2111	0.031*
C11	0.4333 (3)	0.7971 (3)	−0.06454 (17)	0.0154 (5)
C12	0.5725 (3)	0.7927 (3)	0.06883 (18)	0.0202 (5)
H12A	0.6628	0.8253	0.0554	0.030*
H12B	0.5948	0.7182	0.1302	0.030*
H12C	0.4651	0.8842	0.0655	0.030*
C13	0.6907 (3)	0.5769 (3)	0.00148 (17)	0.0149 (5)
C14	0.9101 (3)	0.3590 (3)	0.03247 (17)	0.0174 (5)
H14	1.0126	0.2734	0.0613	0.021*
C15	0.8874 (4)	0.2440 (3)	−0.08522 (19)	0.0203 (5)
H15A	1.0015	0.1650	−0.0615	0.030*
H15B	0.8865	0.2908	−0.1511	0.030*
H15C	0.8110	0.1950	−0.0731	0.030*
C16	0.6894 (3)	0.5071 (3)	−0.06174 (17)	0.0159 (5)
C17	1.2518 (3)	−0.1069 (3)	0.28803 (19)	0.0200 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag	0.01694 (11)	0.01610 (12)	0.01605 (11)	−0.00609 (8)	−0.00257 (7)	−0.00519 (8)
S1	0.0131 (3)	0.0120 (3)	0.0189 (3)	−0.0024 (2)	0.0012 (2)	−0.0038 (2)
F1	0.0277 (9)	0.0307 (10)	0.0546 (12)	−0.0190 (8)	0.0034 (9)	−0.0122 (9)
F2	0.0281 (9)	0.0136 (8)	0.0456 (11)	−0.0009 (7)	0.0068 (8)	−0.0071 (8)
F3	0.0466 (12)	0.0338 (10)	0.0181 (8)	−0.0151 (9)	0.0034 (8)	−0.0013 (7)
O1	0.0206 (10)	0.0245 (10)	0.0188 (9)	−0.0079 (8)	−0.0022 (8)	−0.0080 (8)
O2	0.0214 (10)	0.0174 (10)	0.0259 (10)	−0.0028 (8)	−0.0015 (8)	−0.0078 (8)
O3	0.0203 (9)	0.0267 (11)	0.0209 (10)	−0.0088 (8)	−0.0008 (8)	−0.0129 (8)
O4	0.0192 (9)	0.0153 (9)	0.0216 (9)	−0.0038 (7)	−0.0007 (7)	−0.0060 (7)
O1w	0.0198 (10)	0.0333 (11)	0.0189 (9)	−0.0131 (9)	0.0027 (8)	−0.0122 (9)
O5	0.0284 (11)	0.0232 (11)	0.0189 (10)	0.0030 (9)	0.0027 (8)	−0.0059 (8)
O6	0.0157 (9)	0.0203 (10)	0.0511 (14)	−0.0071 (8)	−0.0003 (9)	−0.0095 (10)
O7	0.0154 (9)	0.0161 (9)	0.0239 (10)	−0.0021 (7)	0.0002 (7)	−0.0089 (8)
N1	0.0174 (10)	0.0149 (10)	0.0145 (10)	−0.0062 (9)	−0.0006 (8)	−0.0037 (8)
N2	0.0144 (10)	0.0118 (10)	0.0184 (10)	−0.0037 (8)	−0.0032 (8)	−0.0024 (8)
N3	0.0152 (10)	0.0150 (10)	0.0205 (11)	−0.0066 (9)	−0.0003 (8)	−0.0051 (9)
N4	0.0135 (10)	0.0146 (10)	0.0192 (10)	−0.0049 (8)	−0.0003 (8)	−0.0061 (8)
N5	0.0164 (10)	0.0142 (10)	0.0153 (10)	−0.0059 (8)	−0.0016 (8)	−0.0027 (8)
N6	0.0179 (10)	0.0136 (10)	0.0138 (10)	−0.0053 (8)	0.0002 (8)	−0.0048 (8)
N7	0.0161 (10)	0.0168 (11)	0.0139 (10)	−0.0037 (9)	−0.0013 (8)	−0.0032 (8)
N8	0.0169 (10)	0.0129 (10)	0.0165 (10)	−0.0041 (8)	0.0009 (8)	−0.0037 (8)
C1	0.0161 (12)	0.0153 (12)	0.0160 (11)	−0.0084 (10)	0.0016 (9)	−0.0035 (9)
C2	0.0258 (14)	0.0180 (13)	0.0182 (12)	−0.0079 (11)	0.0015 (10)	−0.0078 (10)
C3	0.0169 (12)	0.0150 (12)	0.0184 (12)	−0.0082 (10)	0.0005 (10)	−0.0025 (10)
C4	0.0163 (12)	0.0160 (12)	0.0250 (13)	−0.0027 (10)	−0.0067 (10)	−0.0049 (10)
C5	0.0135 (11)	0.0141 (11)	0.0163 (11)	−0.0071 (9)	0.0006 (9)	−0.0042 (9)
C6	0.0161 (12)	0.0159 (12)	0.0188 (12)	−0.0065 (10)	0.0004 (9)	−0.0062 (10)
C7	0.0118 (11)	0.0196 (13)	0.0239 (13)	−0.0009 (10)	−0.0030 (10)	−0.0059 (11)
C8	0.0143 (11)	0.0123 (11)	0.0169 (11)	−0.0052 (9)	0.0008 (9)	−0.0046 (9)
C9	0.0141 (11)	0.0153 (12)	0.0164 (11)	−0.0068 (9)	0.0027 (9)	−0.0044 (9)
C10	0.0181 (12)	0.0188 (13)	0.0227 (13)	−0.0065 (10)	−0.0062 (10)	−0.0037 (11)
C11	0.0164 (11)	0.0142 (12)	0.0141 (11)	−0.0068 (9)	0.0007 (9)	−0.0022 (9)
C12	0.0216 (13)	0.0179 (13)	0.0186 (12)	−0.0053 (10)	−0.0015 (10)	−0.0070 (10)
C13	0.0155 (11)	0.0148 (12)	0.0138 (11)	−0.0074 (10)	0.0018 (9)	−0.0025 (9)
C14	0.0157 (12)	0.0163 (12)	0.0162 (12)	−0.0044 (10)	−0.0013 (9)	−0.0033 (10)
C15	0.0230 (13)	0.0165 (12)	0.0213 (13)	−0.0067 (10)	0.0034 (10)	−0.0093 (10)
C16	0.0155 (12)	0.0128 (11)	0.0158 (11)	−0.0036 (9)	0.0014 (9)	−0.0039 (9)
C17	0.0183 (12)	0.0155 (12)	0.0232 (13)	−0.0054 (10)	0.0031 (10)	−0.0054 (10)

Geometric parameters (Å, º) top

Ag—N7	2.213 (2)	N6—C11	1.388 (3)
Ag—N3	2.218 (2)	N6—C12	1.467 (3)
Ag—O1w	2.4347 (19)	N7—C14	1.344 (3)
Ag—O7	2.5591 (19)	N7—C13	1.361 (3)
S1—O6	1.436 (2)	N8—C14	1.335 (3)
S1—O5	1.442 (2)	N8—C16	1.386 (3)
S1—O7	1.4482 (19)	N8—C15	1.468 (3)
S1—C17	1.822 (3)	C1—C8	1.423 (4)
F1—C17	1.334 (3)	C2—H2A	0.9800
F2—C17	1.322 (3)	C2—H2B	0.9800
F3—C17	1.338 (3)	C2—H2C	0.9800
O1—C1	1.227 (3)	C4—H4A	0.9800
O2—C3	1.216 (3)	C4—H4B	0.9800
O3—C9	1.229 (3)	C4—H4C	0.9800
O4—C11	1.213 (3)	C5—C8	1.371 (4)
O1w—H1w	0.8401	C6—H6	0.9500
O1w—H2w	0.8400	C7—H7A	0.9800
N1—C1	1.397 (3)	C7—H7B	0.9800
N1—C3	1.411 (3)	C7—H7C	0.9800
N1—C2	1.473 (3)	C9—C16	1.422 (4)
N2—C5	1.369 (3)	C10—H10A	0.9800
N2—C3	1.388 (3)	C10—H10B	0.9800
N2—C4	1.463 (3)	C10—H10C	0.9800
N3—C6	1.349 (3)	C12—H12A	0.9800
N3—C5	1.365 (3)	C12—H12B	0.9800
N4—C6	1.333 (3)	C12—H12C	0.9800
N4—C8	1.381 (3)	C13—C16	1.370 (4)
N4—C7	1.468 (3)	C14—H14	0.9500
N5—C9	1.392 (3)	C15—H15A	0.9800
N5—C11	1.415 (3)	C15—H15B	0.9800
N5—C10	1.471 (3)	C15—H15C	0.9800
N6—C13	1.368 (3)

N7—Ag—N3	165.48 (8)	H4A—C4—H4C	109.5
N7—Ag—O1w	98.70 (8)	H4B—C4—H4C	109.5
N3—Ag—O1w	95.81 (7)	N3—C5—N2	127.2 (2)
N7—Ag—O7	90.01 (7)	N3—C5—C8	110.6 (2)
N3—Ag—O7	88.93 (7)	N2—C5—C8	122.2 (2)
O1w—Ag—O7	92.39 (7)	N4—C6—N3	113.1 (2)
O6—S1—O5	115.21 (14)	N4—C6—H6	123.5
O6—S1—O7	114.71 (13)	N3—C6—H6	123.5
O5—S1—O7	114.71 (12)	N4—C7—H7A	109.5
O6—S1—C17	104.22 (13)	N4—C7—H7B	109.5
O5—S1—C17	103.14 (13)	H7A—C7—H7B	109.5
O7—S1—C17	102.51 (12)	N4—C7—H7C	109.5
Ag—O1w—H1w	123.9	H7A—C7—H7C	109.5
Ag—O1w—H2w	125.1	H7B—C7—H7C	109.5
H1W—O1w—H2w	111.1	C5—C8—N4	106.2 (2)
S1—O7—Ag	136.78 (12)	C5—C8—C1	122.5 (2)
C1—N1—C3	126.5 (2)	N4—C8—C1	131.3 (2)
C1—N1—C2	116.8 (2)	O3—C9—N5	122.4 (2)
C3—N1—C2	116.7 (2)	O3—C9—C16	125.2 (2)
C5—N2—C3	119.6 (2)	N5—C9—C16	112.4 (2)
C5—N2—C4	121.2 (2)	N5—C10—H10A	109.5
C3—N2—C4	119.1 (2)	N5—C10—H10B	109.5
C6—N3—C5	103.9 (2)	H10A—C10—H10B	109.5
C6—N3—Ag	119.15 (18)	N5—C10—H10C	109.5
C5—N3—Ag	136.34 (18)	H10A—C10—H10C	109.5
C6—N4—C8	106.3 (2)	H10B—C10—H10C	109.5
C6—N4—C7	126.5 (2)	O4—C11—N6	122.3 (2)
C8—N4—C7	127.3 (2)	O4—C11—N5	121.0 (2)
C9—N5—C11	126.4 (2)	N6—C11—N5	116.6 (2)
C9—N5—C10	117.3 (2)	N6—C12—H12A	109.5
C11—N5—C10	116.0 (2)	N6—C12—H12B	109.5
C13—N6—C11	119.6 (2)	H12A—C12—H12B	109.5
C13—N6—C12	120.8 (2)	N6—C12—H12C	109.5
C11—N6—C12	119.6 (2)	H12A—C12—H12C	109.5
C14—N7—C13	104.0 (2)	H12B—C12—H12C	109.5
C14—N7—Ag	119.11 (17)	N7—C13—N6	127.1 (2)
C13—N7—Ag	136.45 (18)	N7—C13—C16	110.8 (2)
C14—N8—C16	106.0 (2)	N6—C13—C16	122.1 (2)
C14—N8—C15	126.0 (2)	N8—C14—N7	113.2 (2)
C16—N8—C15	127.9 (2)	N8—C14—H14	123.4
O1—C1—N1	121.8 (2)	N7—C14—H14	123.4
O1—C1—C8	125.7 (2)	N8—C15—H15A	109.5
N1—C1—C8	112.5 (2)	N8—C15—H15B	109.5
N1—C2—H2A	109.5	H15A—C15—H15B	109.5
N1—C2—H2B	109.5	N8—C15—H15C	109.5
H2A—C2—H2B	109.5	H15A—C15—H15C	109.5
N1—C2—H2C	109.5	H15B—C15—H15C	109.5
H2A—C2—H2C	109.5	C13—C16—N8	106.0 (2)
H2B—C2—H2C	109.5	C13—C16—C9	122.8 (2)
O2—C3—N2	122.2 (2)	N8—C16—C9	131.2 (2)
O2—C3—N1	121.2 (2)	F2—C17—F1	108.1 (2)
N2—C3—N1	116.6 (2)	F2—C17—F3	107.9 (2)
N2—C4—H4A	109.5	F1—C17—F3	107.0 (2)
N2—C4—H4B	109.5	F2—C17—S1	112.01 (19)
H4A—C4—H4B	109.5	F1—C17—S1	110.82 (19)
N2—C4—H4C	109.5	F3—C17—S1	110.9 (2)

O6—S1—O7—Ag	66.6 (2)	O1—C1—C8—C5	−178.7 (2)
O5—S1—O7—Ag	−70.1 (2)	N1—C1—C8—C5	0.9 (3)
C17—S1—O7—Ag	178.87 (16)	O1—C1—C8—N4	0.7 (5)
N7—Ag—O7—S1	78.84 (17)	N1—C1—C8—N4	−179.7 (2)
N3—Ag—O7—S1	−86.68 (17)	C11—N5—C9—O3	−175.7 (2)
O1w—Ag—O7—S1	177.55 (17)	C10—N5—C9—O3	−2.2 (4)
N7—Ag—N3—C6	−62.4 (4)	C11—N5—C9—C16	4.1 (4)
O1w—Ag—N3—C6	115.84 (19)	C10—N5—C9—C16	177.6 (2)
O7—Ag—N3—C6	23.54 (19)	C13—N6—C11—O4	−179.2 (2)
N7—Ag—N3—C5	128.5 (3)	C12—N6—C11—O4	−2.8 (4)
O1w—Ag—N3—C5	−53.3 (3)	C13—N6—C11—N5	2.8 (3)
O7—Ag—N3—C5	−145.6 (2)	C12—N6—C11—N5	179.2 (2)
N3—Ag—N7—C14	67.4 (4)	C9—N5—C11—O4	177.6 (2)
O1w—Ag—N7—C14	−110.8 (2)	C10—N5—C11—O4	4.1 (4)
O7—Ag—N7—C14	−18.4 (2)	C9—N5—C11—N6	−4.3 (4)
N3—Ag—N7—C13	−121.7 (3)	C10—N5—C11—N6	−177.8 (2)
O1w—Ag—N7—C13	60.1 (3)	C14—N7—C13—N6	178.6 (2)
O7—Ag—N7—C13	152.5 (3)	Ag—N7—C13—N6	6.8 (4)
C3—N1—C1—O1	178.0 (2)	C14—N7—C13—C16	−0.5 (3)
C2—N1—C1—O1	1.0 (4)	Ag—N7—C13—C16	−172.28 (19)
C3—N1—C1—C8	−1.7 (3)	C11—N6—C13—N7	179.3 (2)
C2—N1—C1—C8	−178.6 (2)	C12—N6—C13—N7	2.9 (4)
C5—N2—C3—O2	178.4 (2)	C11—N6—C13—C16	−1.7 (4)
C4—N2—C3—O2	1.6 (4)	C12—N6—C13—C16	−178.1 (2)
C5—N2—C3—N1	−2.3 (3)	C16—N8—C14—N7	0.1 (3)
C4—N2—C3—N1	−179.2 (2)	C15—N8—C14—N7	−178.3 (2)
C1—N1—C3—O2	−178.3 (2)	C13—N7—C14—N8	0.2 (3)
C2—N1—C3—O2	−1.4 (4)	Ag—N7—C14—N8	173.80 (17)
C1—N1—C3—N2	2.4 (4)	N7—C13—C16—N8	0.5 (3)
C2—N1—C3—N2	179.3 (2)	N6—C13—C16—N8	−178.7 (2)
C6—N3—C5—N2	−179.1 (2)	N7—C13—C16—C9	−179.1 (2)
Ag—N3—C5—N2	−8.8 (4)	N6—C13—C16—C9	1.7 (4)
C6—N3—C5—C8	0.6 (3)	C14—N8—C16—C13	−0.3 (3)
Ag—N3—C5—C8	170.88 (18)	C15—N8—C16—C13	178.0 (2)
C3—N2—C5—N3	−178.5 (2)	C14—N8—C16—C9	179.2 (3)
C4—N2—C5—N3	−1.7 (4)	C15—N8—C16—C9	−2.5 (4)
C3—N2—C5—C8	1.8 (4)	O3—C9—C16—C13	177.1 (2)
C4—N2—C5—C8	178.6 (2)	N5—C9—C16—C13	−2.7 (4)
C8—N4—C6—N3	0.5 (3)	O3—C9—C16—N8	−2.4 (5)
C7—N4—C6—N3	−179.7 (2)	N5—C9—C16—N8	177.8 (3)
C5—N3—C6—N4	−0.7 (3)	O6—S1—C17—F2	−62.1 (2)
Ag—N3—C6—N4	−172.98 (17)	O5—S1—C17—F2	58.6 (2)
N3—C5—C8—N4	−0.4 (3)	O7—S1—C17—F2	178.0 (2)
N2—C5—C8—N4	179.4 (2)	O6—S1—C17—F1	177.1 (2)
N3—C5—C8—C1	179.2 (2)	O5—S1—C17—F1	−62.2 (2)
N2—C5—C8—C1	−1.1 (4)	O7—S1—C17—F1	57.3 (2)
C6—N4—C8—C5	0.0 (3)	O6—S1—C17—F3	58.5 (2)
C7—N4—C8—C5	−179.9 (2)	O5—S1—C17—F3	179.17 (19)
C6—N4—C8—C1	−179.5 (3)	O7—S1—C17—F3	−61.4 (2)
C7—N4—C8—C1	0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O1ⁱ	0.84	1.89	2.724 (3)	170
O1w—H2w···O3ⁱⁱ	0.84	1.89	2.701 (3)	163
C10—H10c···O1wⁱⁱ	0.98	2.55	3.428 (4)	149
C15—H15c···O4ⁱⁱ	0.98	2.60	3.382 (4)	137
C4—H4b···O6ⁱⁱⁱ	0.98	2.41	3.252 (4)	144
C12—H12c···O5ⁱⁱⁱ	0.98	2.36	3.278 (4)	155

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

Experimental details

Crystal data
Chemical formula	[Ag(CF₃SO₃)(C₈H₁₀N₄O₂)₂(H₂O)]
M_r	663.36
Crystal system, space group	Triclinic, P1
Temperature (K)	98
a, b, c (Å)	8.9012 (10), 10.0408 (8), 15.457 (2)
α, β, γ (°)	72.091 (7), 85.444 (9), 63.672 (6)
V (Å³)	1175.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.42 × 0.27 × 0.10

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.568, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	7271, 5323, 5140
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.14
No. of reflections	5323
No. of parameters	355
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.86

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Ag—N7	2.213 (2)	Ag—O1w	2.4347 (19)
Ag—N3	2.218 (2)	Ag—O7	2.5591 (19)

N7—Ag—N3	165.48 (8)	N7—Ag—O7	90.01 (7)
N7—Ag—O1w	98.70 (8)	N3—Ag—O7	88.93 (7)
N3—Ag—O1w	95.81 (7)	O1w—Ag—O7	92.39 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O1ⁱ	0.84	1.89	2.724 (3)	170
O1w—H2w···O3ⁱⁱ	0.84	1.89	2.701 (3)	163
C10—H10c···O1wⁱⁱ	0.98	2.55	3.428 (4)	149
C15—H15c···O4ⁱⁱ	0.98	2.60	3.382 (4)	137
C4—H4b···O6ⁱⁱⁱ	0.98	2.41	3.252 (4)	144
C12—H12c···O5ⁱⁱⁱ	0.98	2.36	3.278 (4)	155

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

References

Arman, H. D., Miller, T., Poplaukhin, P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m1167–m1168. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kundu, N., Audhya, A., Towsif Abtab, Sk. Md., Ghosh, S., Tiekink, E. R. T. & Chaudhury, M. (2010). Cryst. Growth Des. 10, 1269–1282. Web of Science CSD CrossRef CAS Google Scholar
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. 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, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page m1211

doi:10.1107/S1600536810035300

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Aqua­(tri­fluoro­methane­sulfonato)­bis­­(1,3,7-tri­methyl­purine-2,6-dione)silver(I)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Aqua(trifluoromethanesulfonato)bis(1,3,7-trimethylpurine-2,6-dione)silver(I)