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In the title complex, {[Ag(C
16H
18N
4)]NO
3}
n, the cationic part forms infinite chains where the Ag
I ions are coordinated in a slightly bent fashion by two N-donor atoms of imidazole rings of two distinct ligand molecules. The nitrate anions interact weakly with the silver cations to form infinite strands running in the
c-axis direction, approximately perpendicular to the cationic chains. The resulting layers are stabilized by offset π–π interactions between benzene rings. Furthermore, a set of C—H
O and π–π interactions (imidazole rings) between adjacent layers results in the formation of a three-dimensional assembly.
Supporting information
CCDC reference: 613726
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.008 Å
- R factor = 0.069
- wR factor = 0.136
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H14B .. O2 .. 3.17 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H7B .. O2 .. 3.07 Ang.
Alert level C
PLAT213_ALERT_2_C Atom C2 has ADP max/min Ratio ............. 3.30 oblate
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N21
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O2 .. 2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. O2 .. 2.66 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C14 .. O2 .. 3.89 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7 .. O2 .. 3.78 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED.
catena-Poly[[silver(I)-µ-1,4-bis(2-methyl-1
H-imidazol-1-
ylmethyl)benzene-
κ2N3:
N3'] nitrate]
top
Crystal data top
[Ag(C16H18N4)]NO3 | F(000) = 880 |
Mr = 436.22 | Dx = 1.790 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1631 reflections |
a = 14.885 (4) Å | θ = 2.8–23.2° |
b = 14.459 (4) Å | µ = 1.27 mm−1 |
c = 7.693 (2) Å | T = 100 K |
β = 102.115 (4)° | Block, colorless |
V = 1618.7 (8) Å3 | 0.12 × 0.10 × 0.09 mm |
Z = 4 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 3702 independent reflections |
Radiation source: fine-focus sealed tube | 2785 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −19→19 |
Tmin = 0.862, Tmax = 0.894 | k = −19→14 |
9697 measured reflections | l = −10→8 |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.05P)2 + 3.538P] where P = (Fo2 + 2Fc2)/3 |
3702 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 1.34 e Å−3 |
0 restraints | Δρmin = −1.34 e Å−3 |
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 | Uiso*/Ueq | |
Ag1 | 0.23577 (3) | 0.15155 (3) | 0.23352 (6) | 0.01987 (16) | |
N1 | 0.0906 (3) | 0.1192 (3) | 0.1824 (7) | 0.0186 (11) | |
C2 | 0.0289 (4) | 0.1327 (4) | 0.0351 (8) | 0.0144 (12) | |
N3 | −0.0543 (3) | 0.0994 (3) | 0.0527 (6) | 0.0125 (10) | |
C4 | −0.0440 (4) | 0.0642 (4) | 0.2206 (8) | 0.0177 (13) | |
H4 | −0.0905 | 0.0369 | 0.2716 | 0.021* | |
C5 | 0.0449 (4) | 0.0758 (4) | 0.2997 (8) | 0.0167 (12) | |
H5 | 0.0721 | 0.0571 | 0.4174 | 0.020* | |
C6 | 0.0464 (4) | 0.1779 (4) | −0.1281 (8) | 0.0192 (13) | |
H6B | 0.1061 | 0.2092 | −0.1007 | 0.029* | |
H6C | −0.0020 | 0.2233 | −0.1712 | 0.029* | |
H6A | 0.0468 | 0.1310 | −0.2200 | 0.029* | |
C7 | −0.1414 (4) | 0.1026 (4) | −0.0791 (8) | 0.0181 (13) | |
H7B | −0.1741 | 0.0432 | −0.0764 | 0.022* | |
H7A | −0.1279 | 0.1096 | −0.1991 | 0.022* | |
C8 | −0.2035 (4) | 0.1808 (4) | −0.0473 (7) | 0.0124 (12) | |
C9 | −0.1780 (4) | 0.2720 (4) | −0.0574 (8) | 0.0149 (12) | |
H9 | −0.1194 | 0.2863 | −0.0809 | 0.018* | |
C10 | −0.2367 (4) | 0.3430 (4) | −0.0335 (7) | 0.0162 (12) | |
H10 | −0.2182 | 0.4055 | −0.0421 | 0.019* | |
C11 | −0.3220 (4) | 0.3238 (4) | 0.0028 (7) | 0.0116 (11) | |
C12 | −0.3485 (4) | 0.2323 (4) | 0.0120 (7) | 0.0155 (12) | |
H12 | −0.4073 | 0.2181 | 0.0349 | 0.019* | |
C13 | −0.2894 (4) | 0.1613 (4) | −0.0124 (8) | 0.0160 (12) | |
H13 | −0.3080 | 0.0988 | −0.0050 | 0.019* | |
C14 | −0.3846 (4) | 0.4027 (4) | 0.0322 (8) | 0.0177 (13) | |
H14A | −0.3970 | 0.3979 | 0.1535 | 0.021* | |
H14B | −0.3531 | 0.4623 | 0.0237 | 0.021* | |
N15 | −0.4722 (3) | 0.4017 (3) | −0.0981 (6) | 0.0134 (10) | |
C16 | −0.4842 (4) | 0.4303 (4) | −0.2722 (8) | 0.0162 (12) | |
H16 | −0.4387 | 0.4552 | −0.3288 | 0.019* | |
C17 | −0.5734 (4) | 0.4160 (4) | −0.3459 (8) | 0.0184 (13) | |
H17 | −0.6016 | 0.4295 | −0.4659 | 0.022* | |
N18 | −0.6182 (3) | 0.3789 (3) | −0.2214 (6) | 0.0147 (10) | |
C19 | −0.5549 (4) | 0.3697 (4) | −0.0730 (8) | 0.0140 (12) | |
C20 | −0.5714 (4) | 0.3320 (4) | 0.0978 (8) | 0.0200 (13) | |
H20B | −0.5705 | 0.3826 | 0.1829 | 0.030* | |
H20A | −0.5233 | 0.2872 | 0.1461 | 0.030* | |
H20C | −0.6315 | 0.3013 | 0.0767 | 0.030* | |
N21 | 0.2435 (3) | 0.3766 (3) | 0.2482 (6) | 0.0153 (10) | |
O1 | 0.2721 (3) | 0.3193 (3) | 0.3695 (5) | 0.0188 (9) | |
O2 | 0.2572 (3) | 0.4602 (3) | 0.2775 (7) | 0.0397 (13) | |
O3 | 0.2000 (3) | 0.3493 (4) | 0.1024 (6) | 0.0347 (12) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0117 (2) | 0.0159 (2) | 0.0314 (3) | −0.00011 (19) | 0.00291 (17) | −0.0031 (2) |
N1 | 0.015 (3) | 0.017 (3) | 0.024 (3) | −0.0006 (19) | 0.004 (2) | −0.005 (2) |
C2 | 0.018 (3) | 0.005 (3) | 0.022 (3) | 0.002 (2) | 0.009 (3) | −0.005 (2) |
N3 | 0.011 (2) | 0.011 (2) | 0.014 (3) | 0.0012 (18) | 0.000 (2) | −0.0002 (19) |
C4 | 0.023 (3) | 0.012 (3) | 0.019 (3) | 0.000 (2) | 0.008 (3) | −0.003 (2) |
C5 | 0.022 (3) | 0.011 (3) | 0.019 (3) | 0.003 (2) | 0.007 (3) | −0.004 (2) |
C6 | 0.022 (3) | 0.010 (3) | 0.027 (4) | 0.002 (2) | 0.010 (3) | −0.001 (2) |
C7 | 0.014 (3) | 0.020 (3) | 0.020 (3) | 0.004 (2) | 0.002 (3) | −0.002 (3) |
C8 | 0.014 (3) | 0.014 (3) | 0.006 (3) | 0.002 (2) | −0.003 (2) | −0.003 (2) |
C9 | 0.015 (3) | 0.014 (3) | 0.018 (3) | −0.001 (2) | 0.007 (2) | −0.001 (2) |
C10 | 0.022 (3) | 0.010 (3) | 0.017 (3) | 0.002 (2) | 0.006 (2) | 0.002 (2) |
C11 | 0.017 (3) | 0.011 (3) | 0.007 (3) | 0.002 (2) | 0.002 (2) | −0.001 (2) |
C12 | 0.013 (3) | 0.018 (3) | 0.016 (3) | −0.001 (2) | 0.005 (2) | −0.003 (2) |
C13 | 0.016 (3) | 0.013 (3) | 0.017 (3) | −0.002 (2) | 0.000 (2) | 0.000 (2) |
C14 | 0.011 (3) | 0.018 (3) | 0.020 (3) | 0.002 (2) | −0.005 (2) | −0.003 (2) |
N15 | 0.012 (2) | 0.009 (2) | 0.019 (3) | 0.0006 (18) | 0.003 (2) | −0.0026 (19) |
C16 | 0.025 (3) | 0.010 (3) | 0.018 (3) | 0.000 (2) | 0.012 (3) | 0.001 (2) |
C17 | 0.027 (3) | 0.007 (3) | 0.021 (3) | 0.003 (2) | 0.005 (3) | −0.004 (2) |
N18 | 0.014 (2) | 0.010 (2) | 0.020 (3) | −0.0005 (18) | 0.003 (2) | −0.0035 (19) |
C19 | 0.018 (3) | 0.009 (3) | 0.018 (3) | 0.004 (2) | 0.009 (3) | −0.003 (2) |
C20 | 0.021 (3) | 0.019 (3) | 0.021 (3) | 0.004 (2) | 0.007 (3) | 0.004 (2) |
N21 | 0.010 (2) | 0.017 (2) | 0.018 (3) | 0.0004 (18) | 0.000 (2) | −0.001 (2) |
O1 | 0.024 (2) | 0.013 (2) | 0.018 (2) | 0.0028 (17) | 0.0012 (19) | 0.0041 (17) |
O2 | 0.050 (3) | 0.016 (2) | 0.054 (3) | 0.006 (2) | 0.012 (3) | 0.007 (2) |
O3 | 0.025 (2) | 0.057 (3) | 0.021 (2) | −0.005 (2) | 0.002 (2) | 0.002 (3) |
Geometric parameters (Å, º) top
Ag1—N1 | 2.165 (5) | C12—H12 | 0.9500 |
Ag1—N18i | 2.173 (5) | C13—C12 | 1.390 (8) |
N1—C2 | 1.314 (7) | C13—C8 | 1.390 (8) |
N1—C5 | 1.389 (7) | C13—H13 | 0.9500 |
C2—C6 | 1.487 (8) | C14—C11 | 1.520 (7) |
N3—C2 | 1.362 (7) | C14—H14A | 0.9900 |
N3—C4 | 1.366 (7) | C14—H14B | 0.9900 |
N3—C7 | 1.469 (7) | N15—C19 | 1.367 (7) |
C4—H4 | 0.9500 | N15—C16 | 1.377 (7) |
C5—C4 | 1.345 (8) | N15—C14 | 1.468 (7) |
C5—H5 | 0.9500 | C16—H16 | 0.9500 |
C6—H6B | 0.9800 | C17—C16 | 1.346 (8) |
C6—H6C | 0.9800 | C17—H17 | 0.9500 |
C6—H6A | 0.9800 | N18—C19 | 1.325 (7) |
C7—C8 | 1.513 (7) | N18—C17 | 1.385 (7) |
C7—H7B | 0.9900 | N18—Ag1ii | 2.173 (5) |
C7—H7A | 0.9900 | C19—C20 | 1.490 (8) |
C8—C9 | 1.380 (8) | C20—H20B | 0.9800 |
C9—H9 | 0.9500 | C20—H20A | 0.9800 |
C10—C11 | 1.384 (8) | C20—H20C | 0.9800 |
C10—C9 | 1.385 (8) | N21—O1 | 1.253 (6) |
C10—H10 | 0.9500 | N21—O2 | 1.239 (6) |
C11—C12 | 1.387 (8) | N21—O3 | 1.236 (6) |
| | | |
N1—Ag1—N18i | 155.78 (17) | C10—C11—C14 | 119.8 (5) |
C2—N1—C5 | 106.2 (5) | C12—C11—C14 | 121.2 (5) |
C2—N1—Ag1 | 127.9 (4) | C11—C12—C13 | 120.2 (5) |
C5—N1—Ag1 | 125.9 (4) | C11—C12—H12 | 119.9 |
N1—C2—N3 | 110.3 (5) | C13—C12—H12 | 119.9 |
N1—C2—C6 | 125.4 (5) | C12—C13—C8 | 120.7 (5) |
N3—C2—C6 | 124.3 (5) | C12—C13—H13 | 119.6 |
C2—N3—C4 | 107.5 (5) | C8—C13—H13 | 119.6 |
C2—N3—C7 | 127.5 (5) | N15—C14—C11 | 112.0 (4) |
C4—N3—C7 | 124.9 (5) | N15—C14—H14A | 109.2 |
C5—C4—N3 | 106.6 (5) | C11—C14—H14A | 109.2 |
C5—C4—H4 | 126.7 | N15—C14—H14B | 109.2 |
N3—C4—H4 | 126.7 | C11—C14—H14B | 109.2 |
C4—C5—N1 | 109.3 (5) | H14A—C14—H14B | 107.9 |
C4—C5—H5 | 125.3 | C19—N15—C16 | 107.6 (5) |
N1—C5—H5 | 125.3 | C19—N15—C14 | 127.2 (5) |
C2—C6—H6B | 109.5 | C16—N15—C14 | 125.2 (5) |
C2—C6—H6C | 109.5 | C17—C16—N15 | 106.2 (5) |
H6B—C6—H6C | 109.5 | C17—C16—H16 | 126.9 |
C2—C6—H6A | 109.5 | N15—C16—H16 | 126.9 |
H6B—C6—H6A | 109.5 | C16—C17—N18 | 110.1 (5) |
H6C—C6—H6A | 109.5 | C16—C17—H17 | 124.9 |
N3—C7—C8 | 113.1 (5) | N18—C17—H17 | 124.9 |
N3—C7—H7B | 109.0 | C19—N18—C17 | 106.0 (5) |
C8—C7—H7B | 109.0 | C19—N18—Ag1ii | 128.6 (4) |
N3—C7—H7A | 109.0 | C17—N18—Ag1ii | 125.4 (4) |
C8—C7—H7A | 109.0 | N18—C19—N15 | 110.1 (5) |
H7B—C7—H7A | 107.8 | N18—C19—C20 | 125.3 (5) |
C9—C8—C13 | 118.7 (5) | N15—C19—C20 | 124.7 (5) |
C9—C8—C7 | 121.4 (5) | C19—C20—H20B | 109.5 |
C13—C8—C7 | 119.9 (5) | C19—C20—H20A | 109.5 |
C8—C9—C10 | 120.8 (5) | H20B—C20—H20A | 109.5 |
C8—C9—H9 | 119.6 | C19—C20—H20C | 109.5 |
C10—C9—H9 | 119.6 | H20B—C20—H20C | 109.5 |
C11—C10—C9 | 120.6 (5) | H20A—C20—H20C | 109.5 |
C11—C10—H10 | 119.7 | O3—N21—O2 | 120.8 (5) |
C9—C10—H10 | 119.7 | O3—N21—O1 | 119.8 (5) |
C10—C11—C12 | 119.0 (5) | O2—N21—O1 | 119.5 (5) |
| | | |
N18i—Ag1—N1—C2 | −108.3 (6) | Ag1ii—N18—C19—C20 | 2.4 (8) |
N18i—Ag1—N1—C5 | 68.9 (7) | C16—N15—C19—N18 | −1.3 (6) |
C19—N18—C17—C16 | −0.9 (6) | C14—N15—C19—N18 | −179.2 (5) |
Ag1ii—N18—C17—C16 | 177.0 (4) | C16—N15—C19—C20 | 179.8 (5) |
C2—N1—C5—C4 | −0.2 (6) | C14—N15—C19—C20 | 2.0 (8) |
Ag1—N1—C5—C4 | −177.9 (4) | N18—C17—C16—N15 | 0.1 (6) |
C2—N3—C7—C8 | −98.9 (6) | C19—N15—C16—C17 | 0.7 (6) |
C4—N3—C7—C8 | 78.7 (7) | C14—N15—C16—C17 | 178.6 (5) |
C12—C13—C8—C9 | 0.0 (8) | N1—C5—C4—N3 | 0.6 (6) |
C12—C13—C8—C7 | −178.1 (5) | C2—N3—C4—C5 | −0.8 (6) |
N3—C7—C8—C9 | 63.6 (7) | C7—N3—C4—C5 | −178.8 (5) |
N3—C7—C8—C13 | −118.3 (6) | C19—N15—C14—C11 | 100.9 (6) |
C5—N1—C2—N3 | −0.3 (6) | C16—N15—C14—C11 | −76.5 (7) |
Ag1—N1—C2—N3 | 177.3 (3) | C9—C10—C11—C12 | −1.1 (8) |
C5—N1—C2—C6 | 179.5 (5) | C9—C10—C11—C14 | 178.8 (5) |
Ag1—N1—C2—C6 | −2.9 (8) | N15—C14—C11—C10 | 119.7 (6) |
C4—N3—C2—N1 | 0.7 (6) | N15—C14—C11—C12 | −60.5 (7) |
C7—N3—C2—N1 | 178.6 (5) | C10—C11—C12—C13 | 1.0 (8) |
C4—N3—C2—C6 | −179.1 (5) | C14—C11—C12—C13 | −178.9 (5) |
C7—N3—C2—C6 | −1.2 (8) | C8—C13—C12—C11 | −0.5 (8) |
C17—N18—C19—N15 | 1.4 (6) | C13—C8—C9—C10 | −0.1 (8) |
Ag1ii—N18—C19—N15 | −176.5 (3) | C7—C8—C9—C10 | 178.0 (5) |
C17—N18—C19—C20 | −179.8 (5) | C11—C10—C9—C8 | 0.7 (9) |
Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) x−1, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O2iii | 0.95 | 2.64 | 3.387 (7) | 136 |
C14—H14b···O2iii | 0.99 | 3.17 | 3.886 (8) | 130 |
C13—H13···O2iv | 0.95 | 2.66 | 3.404 (8) | 135 |
C7—H7b···O2iv | 0.99 | 3.07 | 3.778 (8) | 129 |
Symmetry codes: (iii) −x, −y+1, −z; (iv) −x, y−1/2, −z+1/2. |
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