catena-Poly[silver(I)-μ-2-phenyl­imidazolato-κ²N:N′]

The asymmetric unit of the title compound, [Ag(C₉H₇N₂)]_n, contains two independent Ag^I ions and two 2-phenyl­imidazolate (L) ligands. Each Ag^I centre is linearly coordinated by two N atoms [Ag—N 2.092 (3)–2.097 (3) Å]. Ligands L bridge Ag^I 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.041
• wR factor = 0.068
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.63

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.634
            Tmax scaled      0.634 Tmin scaled      0.586
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.46
           From the CIF: _reflns_number_total               3905
           Count of symmetry unique reflns         2135
           Completeness (_total/calc)            182.90%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1770
           Fraction of Friedel pairs measured     0.829
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1         (9)       1.03
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag2         (9)       1.02
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

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

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S1. Comment

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 1D ligand-bridged-Ag(I) chain structure, which is further extended to form a 3D 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 1D 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 1D 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 1D 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

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

S2. Experimental

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.

S3. Refinement

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

Computing details

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

	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].
	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)]

Crystal data

[Ag(C9H7N2)]	F(000) = 488
Mr = 251.04	Dx = 1.933 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8115 reflections
a = 10.091 (2) Å	θ = 3.3–27.5°
b = 6.9995 (14) Å	µ = 2.28 mm^−1
c = 12.470 (3) Å	T = 293 K
β = 101.59 (3)°	Block, colourless
V = 862.8 (3) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3905 independent reflections
Radiation source: fine-focus sealed tube	3209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ϕ and ω scan	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan SADABS (Bruker, 1998)	h = −13→13
Tmin = 0.924, Tmax = 1.000	k = −9→9
9131 measured reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.068	w = 1/[σ^2(Fo^2) + (0.015P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
3905 reflections	Δρmax = 0.60 e Å^−3
217 parameters	Δρmin = −0.35 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (4)

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
Ag1	1.01351 (4)	0.61504 (6)	0.37721 (2)	0.04521 (13)
Ag2	1.04157 (4)	0.63552 (5)	0.88088 (2)	0.05074 (14)
N1	1.0799 (4)	0.6277 (9)	0.2284 (2)	0.0429 (9)
N2	1.0931 (4)	0.6167 (9)	0.0521 (3)	0.0420 (10)
N3	0.9598 (4)	0.5982 (8)	0.5304 (2)	0.0422 (11)
N4	0.9737 (4)	0.6318 (10)	0.7105 (3)	0.0447 (10)
C1	1.2115 (5)	0.5983 (12)	0.2218 (3)	0.0536 (16)
H1A	1.2835	0.5844	0.2809	0.064*
C2	1.2200 (5)	0.5929 (10)	0.1145 (4)	0.0518 (16)
H2A	1.2989	0.5757	0.0879	0.062*
C3	1.0099 (4)	0.6291 (18)	0.1249 (3)	0.0335 (11)
C4	0.8623 (5)	0.6610 (9)	0.0921 (3)	0.0357 (14)
C5	0.7890 (5)	0.5820 (8)	−0.0049 (3)	0.0424 (13)
H5A	0.8331	0.5050	−0.0475	0.051*
C6	0.6528 (5)	0.6166 (11)	−0.0384 (4)	0.0596 (14)
H6A	0.6062	0.5673	−0.1046	0.071*
C7	0.5846 (6)	0.7250 (9)	0.0265 (5)	0.0701 (19)
H7A	0.4924	0.7476	0.0041	0.084*
C8	0.6537 (6)	0.7985 (8)	0.1235 (5)	0.0546 (15)
H8A	0.6080	0.8691	0.1678	0.065*
C9	0.7912 (6)	0.7680 (7)	0.1555 (4)	0.0454 (14)
H9A	0.8372	0.8203	0.2210	0.055*
C10	0.8325 (5)	0.5729 (9)	0.5531 (4)	0.0505 (18)
H10A	0.7538	0.5457	0.5024	0.061*
C11	0.8428 (5)	0.5950 (12)	0.6630 (4)	0.0554 (17)
H11A	0.7715	0.5864	0.6998	0.067*
C12	1.0415 (4)	0.628 (2)	0.6275 (3)	0.0359 (9)
C13	1.1888 (5)	0.6649 (9)	0.6416 (3)	0.0393 (14)
C14	1.2641 (6)	0.5643 (8)	0.5782 (4)	0.0543 (16)
H14A	1.2222	0.4726	0.5288	0.065*
C15	1.4013 (6)	0.6000 (11)	0.5883 (4)	0.0703 (17)
H15A	1.4513	0.5322	0.5460	0.084*
C16	1.4629 (7)	0.7352 (11)	0.6606 (6)	0.081 (2)
H16A	1.5544	0.7602	0.6653	0.098*
C17	1.3931 (7)	0.8356 (9)	0.7269 (5)	0.0691 (18)
H17A	1.4367	0.9251	0.7769	0.083*
C18	1.2549 (6)	0.7987 (8)	0.7164 (4)	0.0509 (14)
H18A	1.2060	0.8648	0.7603	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0583 (2)	0.0590 (3)	0.01865 (16)	−0.0022 (4)	0.00847 (14)	−0.0002 (2)
Ag2	0.0724 (3)	0.0617 (4)	0.02221 (18)	0.0098 (4)	0.01922 (15)	0.0024 (3)
N1	0.053 (2)	0.058 (3)	0.0187 (16)	−0.003 (5)	0.0101 (15)	−0.003 (3)
N2	0.056 (2)	0.049 (3)	0.0236 (17)	0.005 (4)	0.0143 (15)	−0.004 (3)
N3	0.054 (2)	0.054 (3)	0.0194 (17)	−0.002 (3)	0.0085 (15)	−0.003 (2)
N4	0.055 (2)	0.059 (3)	0.0235 (17)	0.012 (5)	0.0160 (16)	0.005 (3)
C1	0.047 (3)	0.080 (5)	0.032 (2)	0.015 (4)	0.004 (2)	0.009 (4)
C2	0.053 (3)	0.059 (5)	0.048 (3)	0.013 (4)	0.022 (2)	0.006 (3)
C3	0.047 (3)	0.035 (3)	0.0197 (19)	−0.018 (6)	0.0108 (16)	−0.008 (4)
C4	0.047 (3)	0.038 (4)	0.024 (2)	−0.005 (3)	0.0117 (19)	0.004 (3)
C5	0.054 (3)	0.043 (4)	0.032 (2)	−0.003 (3)	0.013 (2)	−0.005 (3)
C6	0.060 (3)	0.070 (4)	0.043 (3)	−0.022 (5)	−0.003 (2)	−0.003 (4)
C7	0.041 (4)	0.087 (5)	0.081 (5)	−0.010 (3)	0.011 (3)	0.016 (4)
C8	0.048 (4)	0.060 (4)	0.057 (4)	0.005 (3)	0.017 (3)	0.001 (3)
C9	0.053 (4)	0.049 (3)	0.036 (3)	−0.004 (3)	0.012 (3)	−0.003 (3)
C10	0.047 (3)	0.067 (6)	0.037 (3)	−0.003 (3)	0.006 (2)	0.002 (3)
C11	0.055 (3)	0.075 (5)	0.041 (3)	0.013 (4)	0.023 (2)	0.012 (4)
C12	0.050 (3)	0.039 (3)	0.0212 (19)	−0.002 (5)	0.0126 (16)	0.000 (4)
C13	0.052 (3)	0.046 (4)	0.020 (2)	0.008 (3)	0.0083 (19)	0.005 (3)
C14	0.057 (4)	0.063 (4)	0.043 (3)	0.007 (3)	0.007 (3)	−0.012 (3)
C15	0.060 (4)	0.085 (5)	0.070 (4)	0.017 (5)	0.023 (3)	−0.007 (4)
C16	0.047 (4)	0.103 (6)	0.090 (5)	0.003 (4)	0.005 (4)	0.001 (5)
C17	0.063 (5)	0.074 (5)	0.061 (4)	−0.003 (4)	−0.010 (4)	−0.009 (3)
C18	0.062 (4)	0.056 (4)	0.034 (3)	0.007 (3)	0.007 (3)	−0.003 (3)

Geometric parameters (Å, º)

Ag1—N1	2.097 (3)	C6—H6A	0.9300
Ag1—N3	2.092 (3)	C7—C8	1.370 (8)
Ag2—N2^i	2.097 (3)	C7—H7A	0.9300
Ag2—N4	2.097 (3)	C8—C9	1.381 (7)
N1—C3	1.342 (4)	C8—H8A	0.9300
N1—C1	1.363 (5)	C9—H9A	0.9300
N2—C3	1.358 (5)	C10—C11	1.362 (6)
N2—C2	1.368 (6)	C10—H10A	0.9300
N2—Ag2^ii	2.097 (3)	C11—H11A	0.9300
N3—C12	1.338 (5)	C12—C13	1.484 (6)
N3—C10	1.381 (6)	C13—C14	1.393 (6)
N4—C12	1.351 (4)	C13—C18	1.394 (7)
N4—C11	1.359 (6)	C14—C15	1.387 (7)
C1—C2	1.358 (6)	C14—H14A	0.9300
C1—H1A	0.9300	C15—C16	1.367 (9)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.480 (7)	C16—C17	1.381 (9)
C4—C9	1.388 (7)	C16—H16A	0.9300
C4—C5	1.399 (6)	C17—C18	1.399 (8)
C5—C6	1.375 (7)	C17—H17A	0.9300
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.388 (8)
N3—Ag1—N1	176.40 (15)	C6—C7—H7A	120.1
N4—Ag2—N2^i	173.72 (19)	C7—C8—C9	120.0 (5)
C3—N1—C1	105.9 (3)	C7—C8—H8A	120.0
C3—N1—Ag1	130.7 (3)	C9—C8—H8A	120.0
C1—N1—Ag1	122.4 (3)	C8—C9—C4	121.5 (5)
C3—N2—C2	105.1 (3)	C8—C9—H9A	119.2
C3—N2—Ag2^ii	128.1 (3)	C4—C9—H9A	119.2
C2—N2—Ag2^ii	126.8 (3)	C11—C10—N3	107.8 (4)
C12—N3—C10	105.4 (3)	C11—C10—H10A	126.1
C12—N3—Ag1	126.3 (3)	N3—C10—H10A	126.1
C10—N3—Ag1	128.1 (3)	N4—C11—C10	109.3 (4)
C12—N4—C11	105.1 (4)	N4—C11—H11A	125.3
C12—N4—Ag2	131.6 (3)	C10—C11—H11A	125.3
C11—N4—Ag2	122.3 (3)	N3—C12—N4	112.4 (4)
C2—C1—N1	108.6 (4)	N3—C12—C13	123.7 (3)
C2—C1—H1A	125.7	N4—C12—C13	123.8 (4)
N1—C1—H1A	125.7	C14—C13—C18	118.6 (5)
C1—C2—N2	108.7 (4)	C14—C13—C12	119.6 (6)
C1—C2—H2A	125.7	C18—C13—C12	121.8 (6)
N2—C2—H2A	125.7	C15—C14—C13	120.3 (5)
N1—C3—N2	111.5 (4)	C15—C14—H14A	119.8
N1—C3—C4	125.0 (4)	C13—C14—H14A	119.8
N2—C3—C4	123.3 (4)	C16—C15—C14	119.9 (6)
C9—C4—C5	117.5 (5)	C16—C15—H15A	120.1
C9—C4—C3	122.0 (5)	C14—C15—H15A	120.1
C5—C4—C3	120.4 (5)	C15—C16—C17	121.8 (6)
C6—C5—C4	121.0 (5)	C15—C16—H16A	119.1
C6—C5—H5A	119.5	C17—C16—H16A	119.1
C4—C5—H5A	119.5	C16—C17—C18	118.0 (6)
C5—C6—C7	120.1 (5)	C16—C17—H17A	121.0
C5—C6—H6A	119.9	C18—C17—H17A	121.0
C7—C6—H6A	119.9	C13—C18—C17	121.3 (5)
C8—C7—C6	119.8 (5)	C13—C18—H18A	119.3
C8—C7—H7A	120.1	C17—C18—H18A	119.3
C3—N1—C1—C2	3.3 (10)	C12—N3—C10—C11	1.8 (10)
Ag1—N1—C1—C2	172.7 (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)
Ag2^ii—N2—C2—C1	176.6 (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—N4	171.8 (6)
C1—N1—C3—C4	−178.6 (10)	C10—N3—C12—C13	−179.3 (11)
Ag1—N1—C3—C4	13.2 (16)	Ag1—N3—C12—C13	−5.0 (17)
C2—N2—C3—N1	4.4 (11)	C11—N4—C12—N3	2.1 (13)
Ag2^ii—N2—C3—N1	−174.4 (5)	Ag2—N4—C12—N3	170.6 (6)
C2—N2—C3—C4	178.3 (9)	C11—N4—C12—C13	178.9 (11)
Ag2^ii—N2—C3—C4	−0.5 (15)	Ag2—N4—C12—C13	−12.6 (18)
N1—C3—C4—C9	27.6 (14)	N3—C12—C13—C14	−39.2 (16)
N2—C3—C4—C9	−145.5 (9)	N4—C12—C13—C14	144.4 (10)
N1—C3—C4—C5	−152.0 (9)	N3—C12—C13—C18	140.4 (10)
N2—C3—C4—C5	34.9 (13)	N4—C12—C13—C18	−36.1 (16)
C9—C4—C5—C6	2.8 (8)	C18—C13—C14—C15	−1.2 (8)
C3—C4—C5—C6	−177.5 (7)	C12—C13—C14—C15	178.4 (7)
C4—C5—C6—C7	−2.6 (9)	C13—C14—C15—C16	−0.2 (9)
C5—C6—C7—C8	0.5 (10)	C14—C15—C16—C17	1.6 (10)
C6—C7—C8—C9	1.3 (9)	C15—C16—C17—C18	−1.5 (10)
C7—C8—C9—C4	−1.0 (9)	C14—C13—C18—C17	1.4 (8)
C5—C4—C9—C8	−1.1 (8)	C12—C13—C18—C17	−178.2 (7)
C3—C4—C9—C8	179.3 (6)	C16—C17—C18—C13	0.0 (9)

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