Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705533X/cv2336sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705533X/cv2336Isup2.hkl |
CCDC reference: 672618
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.
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).
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.
[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) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
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 on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.015P)2] where P = (Fo2 + 2Fc2)/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) |
[Ag(C9H7N2)] | V = 862.8 (3) Å3 |
Mr = 251.04 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.091 (2) Å | µ = 2.28 mm−1 |
b = 6.9995 (14) Å | T = 293 K |
c = 12.470 (3) Å | 0.30 × 0.20 × 0.20 mm |
β = 101.59 (3)° |
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 = 1.000 | Rint = 0.042 |
9131 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.068 | Δρmax = 0.60 e Å−3 |
S = 1.00 | Δρmin = −0.35 e Å−3 |
3905 reflections | Absolute structure: Flack (1983) |
217 parameters | Absolute structure parameter: −0.01 (4) |
1 restraint |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
Ag1—N1 | 2.097 (3) | C6—H6A | 0.9300 |
Ag1—N3 | 2.092 (3) | C7—C8 | 1.370 (8) |
Ag2—N2i | 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—Ag2ii | 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—N2i | 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—Ag2ii | 128.1 (3) | C4—C9—H9A | 119.2 |
C2—N2—Ag2ii | 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) |
Ag2ii—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) |
Ag2ii—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) |
Ag2ii—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. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C9H7N2)] |
Mr | 251.04 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 10.091 (2), 6.9995 (14), 12.470 (3) |
β (°) | 101.59 (3) |
V (Å3) | 862.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.28 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan SADABS (Bruker, 1998) |
Tmin, Tmax | 0.924, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9131, 3905, 3209 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.068, 1.00 |
No. of reflections | 3905 |
No. of parameters | 217 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.60, −0.35 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.01 (4) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
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).