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Acta Cryst. (2007). E63, m2952    [ doi:10.1107/S160053680705533X ]

catena-Poly[silver(I)-[mu]-2-phenylimidazolato-[kappa]2N:N']

Q. Gao, J.-B. Feng, C.-Y. Zhang and Y.-B. Xie

Abstract top

The asymmetric unit of the title compound, [Ag(C9H7N2)]n, contains two independent AgI ions and two 2-phenylimidazolate (L) ligands. Each AgI centre is linearly coordinated by two N atoms [Ag-N 2.092 (3)-2.097 (3) Å]. Ligands L bridge AgI ions into polymeric chains parallel to the c axis, with Ag...Ag separations of 6.232 (2) and 6.254 (2) Å. No interactions between the Ag centres from neighbouring chains are observed.

Comment top

The crystal structures of silver(I) imidazolate, catena-poly[(m/2-2-imidazolato-N,N')-silver(I)] (Huang et al., 2006) and silver(I) methylimidazolate, catena-poly[(m/2-2-methylimidazolato-N,N')-silver(I)] (Liu & Zhu, 2005) have been reported recently. Both complexes take a one-dimensional ligand-bridged-Ag(I) chain structure, which is further extended to form a three-dimensional framework through Ag—Ag interactions. On the other hand, for the 2-phenylimidazolate ligand, only one metal complex was documented (Mukhopadhyay & Pal, 2006). Herein, we report the structure of silver(I) 2-phenylimidazolate, [Ag2(C9H7N2)2]n (I), which has also a one-dimensional ligand-bridged chain structure, however, without Ag—Ag interactions that may be attributed to the bulky substituent 2-phenylimidazolate, which isolates the chains.

As shown in Figure 1, (I) has a one-dimensional chain structure, in which there exist two crystallographically independent Ag(I) ions Ag1 and Ag2 and two 2-phenylimidazolate ligands with similar coordination environments, respectively. Each Ag(I) center linearly coordinates to two N atoms from two ligands with the N—Ag—N angles of 176.40 (15) and 173.72 (19) ° for Ag1 and Ag2, respectively. Simultaneously, each 2-phenylimidazolate group bridges two Ag(I) ions to form a one-dimensional chain related by a 21 axis, with the Ag—Ag separations of 6.232 (2) [Ag1—Ag2] and 6.254 (2) Å [Ag1—Ag2B]. The dihedral angles between benzene ring and imidazole ring are 31.1 (2) ° for [ring C4—C9 and C1—C3—N1—N2] and 37.6 (2) ° for [ring C13—C18 and C10—C11—N3—N4], respectively. In the crystal, these chains are packed parallel along the c direction and without Ag—Ag or other weak interactions (Figure 2).

Related literature top

For related polymeric crystal structures, see: Liu & Zhu (2005); Mukhopadhyay & Pal (2006); Huang et al. (2006).

Experimental top

A mixture of 2-phenylimidazole (43 mg, 0.3 mmol) and AgNO3 (51 mg, 0.3 mmol) was dissolved in 10 ml of ammonium hydroxide (20%). The resulted solution was filtered and filtrate was allowed to stand for 15 days in the dark. Colourless crystals of (I) were collected, in about 30% yield.

Refinement top

H atoms were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A portion of polymeric one-dimensional chain structure of (I), showing the atomic numbering and 30% probabilty displacement ellipsoids [symmetry codes: (A) x, y, 1 + z; (B) x, y, z − 1].
[Figure 2] Fig. 2. A portion of crystal packing viewed approximately down the b axis. H atoms omitted for clarity.
catena-Poly[(m/2-2-phenylimidazolato-N,N')-silver(I)] top
Crystal data top
[Ag(C9H7N2)]F000 = 488
Mr = 251.04Dx = 1.933 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8115 reflections
a = 10.091 (2) Åθ = 3.3–27.5º
b = 6.9995 (14) ŵ = 2.28 mm−1
c = 12.470 (3) ÅT = 293 (2) K
β = 101.59 (3)ºBlock, colourless
V = 862.8 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3905 independent reflections
Radiation source: fine-focus sealed tube3209 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
T = 293(2) Kθmax = 27.5º
φ and ω scanθmin = 3.3º
Absorption correction: multi-scan
SADABS (Bruker, 1998)		h = −13→13
Tmin = 0.924, Tmax = 1.000k = −9→9
9131 measured reflectionsl = −16→16
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041  w = 1/[σ2(Fo2) + (0.015P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.068(Δ/σ)max = 0.001
S = 1.00Δρmax = 0.60 e Å−3
3905 reflectionsΔρmin = −0.35 e Å−3
217 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (4)
Secondary atom site location: difference Fourier map
Crystal data top
[Ag(C9H7N2)]V = 862.8 (3) Å3
Mr = 251.04Z = 4
Monoclinic, P21Mo Kα
a = 10.091 (2) ŵ = 2.28 mm−1
b = 6.9995 (14) ÅT = 293 (2) K
c = 12.470 (3) Å0.30 × 0.20 × 0.20 mm
β = 101.59 (3)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		3905 independent reflections
Absorption correction: multi-scan
SADABS (Bruker, 1998)		3209 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 1.000Rint = 0.042
9131 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.068Δρmax = 0.60 e Å−3
S = 1.00Δρmin = −0.35 e Å−3
3905 reflectionsAbsolute structure: Flack (1983)
217 parametersFlack parameter: −0.01 (4)
1 restraint
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
xyzUiso*/Ueq
Ag11.01351 (4)0.61504 (6)0.37721 (2)0.04521 (13)
Ag21.04157 (4)0.63552 (5)0.88088 (2)0.05074 (14)
N11.0799 (4)0.6277 (9)0.2284 (2)0.0429 (9)
N21.0931 (4)0.6167 (9)0.0521 (3)0.0420 (10)
N30.9598 (4)0.5982 (8)0.5304 (2)0.0422 (11)
N40.9737 (4)0.6318 (10)0.7105 (3)0.0447 (10)
C11.2115 (5)0.5983 (12)0.2218 (3)0.0536 (16)
H1A1.28350.58440.28090.064*
C21.2200 (5)0.5929 (10)0.1145 (4)0.0518 (16)
H2A1.29890.57570.08790.062*
C31.0099 (4)0.6291 (18)0.1249 (3)0.0335 (11)
C40.8623 (5)0.6610 (9)0.0921 (3)0.0357 (14)
C50.7890 (5)0.5820 (8)−0.0049 (3)0.0424 (13)
H5A0.83310.5050−0.04750.051*
C60.6528 (5)0.6166 (11)−0.0384 (4)0.0596 (14)
H6A0.60620.5673−0.10460.071*
C70.5846 (6)0.7250 (9)0.0265 (5)0.0701 (19)
H7A0.49240.74760.00410.084*
C80.6537 (6)0.7985 (8)0.1235 (5)0.0546 (15)
H8A0.60800.86910.16780.065*
C90.7912 (6)0.7680 (7)0.1555 (4)0.0454 (14)
H9A0.83720.82030.22100.055*
C100.8325 (5)0.5729 (9)0.5531 (4)0.0505 (18)
H10A0.75380.54570.50240.061*
C110.8428 (5)0.5950 (12)0.6630 (4)0.0554 (17)
H11A0.77150.58640.69980.067*
C121.0415 (4)0.628 (2)0.6275 (3)0.0359 (9)
C131.1888 (5)0.6649 (9)0.6416 (3)0.0393 (14)
C141.2641 (6)0.5643 (8)0.5782 (4)0.0543 (16)
H14A1.22220.47260.52880.065*
C151.4013 (6)0.6000 (11)0.5883 (4)0.0703 (17)
H15A1.45130.53220.54600.084*
C161.4629 (7)0.7352 (11)0.6606 (6)0.081 (2)
H16A1.55440.76020.66530.098*
C171.3931 (7)0.8356 (9)0.7269 (5)0.0691 (18)
H17A1.43670.92510.77690.083*
C181.2549 (6)0.7987 (8)0.7164 (4)0.0509 (14)
H18A1.20600.86480.76030.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0583 (2)0.0590 (3)0.01865 (16)−0.0022 (4)0.00847 (14)−0.0002 (2)
Ag20.0724 (3)0.0617 (4)0.02221 (18)0.0098 (4)0.01922 (15)0.0024 (3)
N10.053 (2)0.058 (3)0.0187 (16)−0.003 (5)0.0101 (15)−0.003 (3)
N20.056 (2)0.049 (3)0.0236 (17)0.005 (4)0.0143 (15)−0.004 (3)
N30.054 (2)0.054 (3)0.0194 (17)−0.002 (3)0.0085 (15)−0.003 (2)
N40.055 (2)0.059 (3)0.0235 (17)0.012 (5)0.0160 (16)0.005 (3)
C10.047 (3)0.080 (5)0.032 (2)0.015 (4)0.004 (2)0.009 (4)
C20.053 (3)0.059 (5)0.048 (3)0.013 (4)0.022 (2)0.006 (3)
C30.047 (3)0.035 (3)0.0197 (19)−0.018 (6)0.0108 (16)−0.008 (4)
C40.047 (3)0.038 (4)0.024 (2)−0.005 (3)0.0117 (19)0.004 (3)
C50.054 (3)0.043 (4)0.032 (2)−0.003 (3)0.013 (2)−0.005 (3)
C60.060 (3)0.070 (4)0.043 (3)−0.022 (5)−0.003 (2)−0.003 (4)
C70.041 (4)0.087 (5)0.081 (5)−0.010 (3)0.011 (3)0.016 (4)
C80.048 (4)0.060 (4)0.057 (4)0.005 (3)0.017 (3)0.001 (3)
C90.053 (4)0.049 (3)0.036 (3)−0.004 (3)0.012 (3)−0.003 (3)
C100.047 (3)0.067 (6)0.037 (3)−0.003 (3)0.006 (2)0.002 (3)
C110.055 (3)0.075 (5)0.041 (3)0.013 (4)0.023 (2)0.012 (4)
C120.050 (3)0.039 (3)0.0212 (19)−0.002 (5)0.0126 (16)0.000 (4)
C130.052 (3)0.046 (4)0.020 (2)0.008 (3)0.0083 (19)0.005 (3)
C140.057 (4)0.063 (4)0.043 (3)0.007 (3)0.007 (3)−0.012 (3)
C150.060 (4)0.085 (5)0.070 (4)0.017 (5)0.023 (3)−0.007 (4)
C160.047 (4)0.103 (6)0.090 (5)0.003 (4)0.005 (4)0.001 (5)
C170.063 (5)0.074 (5)0.061 (4)−0.003 (4)−0.010 (4)−0.009 (3)
C180.062 (4)0.056 (4)0.034 (3)0.007 (3)0.007 (3)−0.003 (3)
Geometric parameters (Å, °) top
Ag1—N12.097 (3)C6—H6A0.9300
Ag1—N32.092 (3)C7—C81.370 (8)
Ag2—N2i2.097 (3)C7—H7A0.9300
Ag2—N42.097 (3)C8—C91.381 (7)
N1—C31.342 (4)C8—H8A0.9300
N1—C11.363 (5)C9—H9A0.9300
N2—C31.358 (5)C10—C111.362 (6)
N2—C21.368 (6)C10—H10A0.9300
N2—Ag2ii2.097 (3)C11—H11A0.9300
N3—C121.338 (5)C12—C131.484 (6)
N3—C101.381 (6)C13—C141.393 (6)
N4—C121.351 (4)C13—C181.394 (7)
N4—C111.359 (6)C14—C151.387 (7)
C1—C21.358 (6)C14—H14A0.9300
C1—H1A0.9300C15—C161.367 (9)
C2—H2A0.9300C15—H15A0.9300
C3—C41.480 (7)C16—C171.381 (9)
C4—C91.388 (7)C16—H16A0.9300
C4—C51.399 (6)C17—C181.399 (8)
C5—C61.375 (7)C17—H17A0.9300
C5—H5A0.9300C18—H18A0.9300
C6—C71.388 (8)
N3—Ag1—N1176.40 (15)C6—C7—H7A120.1
N4—Ag2—N2i173.72 (19)C7—C8—C9120.0 (5)
C3—N1—C1105.9 (3)C7—C8—H8A120.0
C3—N1—Ag1130.7 (3)C9—C8—H8A120.0
C1—N1—Ag1122.4 (3)C8—C9—C4121.5 (5)
C3—N2—C2105.1 (3)C8—C9—H9A119.2
C3—N2—Ag2ii128.1 (3)C4—C9—H9A119.2
C2—N2—Ag2ii126.8 (3)C11—C10—N3107.8 (4)
C12—N3—C10105.4 (3)C11—C10—H10A126.1
C12—N3—Ag1126.3 (3)N3—C10—H10A126.1
C10—N3—Ag1128.1 (3)N4—C11—C10109.3 (4)
C12—N4—C11105.1 (4)N4—C11—H11A125.3
C12—N4—Ag2131.6 (3)C10—C11—H11A125.3
C11—N4—Ag2122.3 (3)N3—C12—N4112.4 (4)
C2—C1—N1108.6 (4)N3—C12—C13123.7 (3)
C2—C1—H1A125.7N4—C12—C13123.8 (4)
N1—C1—H1A125.7C14—C13—C18118.6 (5)
C1—C2—N2108.7 (4)C14—C13—C12119.6 (6)
C1—C2—H2A125.7C18—C13—C12121.8 (6)
N2—C2—H2A125.7C15—C14—C13120.3 (5)
N1—C3—N2111.5 (4)C15—C14—H14A119.8
N1—C3—C4125.0 (4)C13—C14—H14A119.8
N2—C3—C4123.3 (4)C16—C15—C14119.9 (6)
C9—C4—C5117.5 (5)C16—C15—H15A120.1
C9—C4—C3122.0 (5)C14—C15—H15A120.1
C5—C4—C3120.4 (5)C15—C16—C17121.8 (6)
C6—C5—C4121.0 (5)C15—C16—H16A119.1
C6—C5—H5A119.5C17—C16—H16A119.1
C4—C5—H5A119.5C16—C17—C18118.0 (6)
C5—C6—C7120.1 (5)C16—C17—H17A121.0
C5—C6—H6A119.9C18—C17—H17A121.0
C7—C6—H6A119.9C13—C18—C17121.3 (5)
C8—C7—C6119.8 (5)C13—C18—H18A119.3
C8—C7—H7A120.1C17—C18—H18A119.3
C3—N1—C1—C23.3 (10)C12—N3—C10—C111.8 (10)
Ag1—N1—C1—C2172.7 (5)Ag1—N3—C10—C11−172.3 (5)
N1—C1—C2—N2−0.6 (9)C12—N4—C11—C10−0.9 (11)
C3—N2—C2—C1−2.2 (10)Ag2—N4—C11—C10−170.7 (4)
Ag2ii—N2—C2—C1176.6 (5)N3—C10—C11—N4−0.6 (10)
C1—N1—C3—N2−4.8 (12)C10—N3—C12—N4−2.5 (12)
Ag1—N1—C3—N2−173.1 (5)Ag1—N3—C12—N4171.8 (6)
C1—N1—C3—C4−178.6 (10)C10—N3—C12—C13−179.3 (11)
Ag1—N1—C3—C413.2 (16)Ag1—N3—C12—C13−5.0 (17)
C2—N2—C3—N14.4 (11)C11—N4—C12—N32.1 (13)
Ag2ii—N2—C3—N1−174.4 (5)Ag2—N4—C12—N3170.6 (6)
C2—N2—C3—C4178.3 (9)C11—N4—C12—C13178.9 (11)
Ag2ii—N2—C3—C4−0.5 (15)Ag2—N4—C12—C13−12.6 (18)
N1—C3—C4—C927.6 (14)N3—C12—C13—C14−39.2 (16)
N2—C3—C4—C9−145.5 (9)N4—C12—C13—C14144.4 (10)
N1—C3—C4—C5−152.0 (9)N3—C12—C13—C18140.4 (10)
N2—C3—C4—C534.9 (13)N4—C12—C13—C18−36.1 (16)
C9—C4—C5—C62.8 (8)C18—C13—C14—C15−1.2 (8)
C3—C4—C5—C6−177.5 (7)C12—C13—C14—C15178.4 (7)
C4—C5—C6—C7−2.6 (9)C13—C14—C15—C16−0.2 (9)
C5—C6—C7—C80.5 (10)C14—C15—C16—C171.6 (10)
C6—C7—C8—C91.3 (9)C15—C16—C17—C18−1.5 (10)
C7—C8—C9—C4−1.0 (9)C14—C13—C18—C171.4 (8)
C5—C4—C9—C8−1.1 (8)C12—C13—C18—C17−178.2 (7)
C3—C4—C9—C8179.3 (6)C16—C17—C18—C130.0 (9)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1.
Acknowledgements top

This work was supported by the Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of Beijing Municipality.

references
References top

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Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.