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In the title complex, {[Ag(C16H18N4)]NO3}n, the cationic part forms infinite chains where the AgI 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023300/hk2058sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023300/hk2058Isup2.hkl
Contains datablock I

CCDC reference: 613726

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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-1H-imidazol-1- ylmethyl)benzene-κ2N3:N3'] nitrate] top
Crystal data top
[Ag(C16H18N4)]NO3F(000) = 880
Mr = 436.22Dx = 1.790 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1631 reflections
a = 14.885 (4) Åθ = 2.8–23.2°
b = 14.459 (4) ŵ = 1.27 mm1
c = 7.693 (2) ÅT = 100 K
β = 102.115 (4)°Block, colorless
V = 1618.7 (8) Å30.12 × 0.10 × 0.09 mm
Z = 4
Data collection top
Bruker APEX CCD area-detector
diffractometer
3702 independent reflections
Radiation source: fine-focus sealed tube2785 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 1919
Tmin = 0.862, Tmax = 0.894k = 1914
9697 measured reflectionsl = 108
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-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 parametersΔρmax = 1.34 e Å3
0 restraintsΔρmin = 1.34 e Å3
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
Ag10.23577 (3)0.15155 (3)0.23352 (6)0.01987 (16)
N10.0906 (3)0.1192 (3)0.1824 (7)0.0186 (11)
C20.0289 (4)0.1327 (4)0.0351 (8)0.0144 (12)
N30.0543 (3)0.0994 (3)0.0527 (6)0.0125 (10)
C40.0440 (4)0.0642 (4)0.2206 (8)0.0177 (13)
H40.09050.03690.27160.021*
C50.0449 (4)0.0758 (4)0.2997 (8)0.0167 (12)
H50.07210.05710.41740.020*
C60.0464 (4)0.1779 (4)0.1281 (8)0.0192 (13)
H6B0.10610.20920.10070.029*
H6C0.00200.22330.17120.029*
H6A0.04680.13100.22000.029*
C70.1414 (4)0.1026 (4)0.0791 (8)0.0181 (13)
H7B0.17410.04320.07640.022*
H7A0.12790.10960.19910.022*
C80.2035 (4)0.1808 (4)0.0473 (7)0.0124 (12)
C90.1780 (4)0.2720 (4)0.0574 (8)0.0149 (12)
H90.11940.28630.08090.018*
C100.2367 (4)0.3430 (4)0.0335 (7)0.0162 (12)
H100.21820.40550.04210.019*
C110.3220 (4)0.3238 (4)0.0028 (7)0.0116 (11)
C120.3485 (4)0.2323 (4)0.0120 (7)0.0155 (12)
H120.40730.21810.03490.019*
C130.2894 (4)0.1613 (4)0.0124 (8)0.0160 (12)
H130.30800.09880.00500.019*
C140.3846 (4)0.4027 (4)0.0322 (8)0.0177 (13)
H14A0.39700.39790.15350.021*
H14B0.35310.46230.02370.021*
N150.4722 (3)0.4017 (3)0.0981 (6)0.0134 (10)
C160.4842 (4)0.4303 (4)0.2722 (8)0.0162 (12)
H160.43870.45520.32880.019*
C170.5734 (4)0.4160 (4)0.3459 (8)0.0184 (13)
H170.60160.42950.46590.022*
N180.6182 (3)0.3789 (3)0.2214 (6)0.0147 (10)
C190.5549 (4)0.3697 (4)0.0730 (8)0.0140 (12)
C200.5714 (4)0.3320 (4)0.0978 (8)0.0200 (13)
H20B0.57050.38260.18290.030*
H20A0.52330.28720.14610.030*
H20C0.63150.30130.07670.030*
N210.2435 (3)0.3766 (3)0.2482 (6)0.0153 (10)
O10.2721 (3)0.3193 (3)0.3695 (5)0.0188 (9)
O20.2572 (3)0.4602 (3)0.2775 (7)0.0397 (13)
O30.2000 (3)0.3493 (4)0.1024 (6)0.0347 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0117 (2)0.0159 (2)0.0314 (3)0.00011 (19)0.00291 (17)0.0031 (2)
N10.015 (3)0.017 (3)0.024 (3)0.0006 (19)0.004 (2)0.005 (2)
C20.018 (3)0.005 (3)0.022 (3)0.002 (2)0.009 (3)0.005 (2)
N30.011 (2)0.011 (2)0.014 (3)0.0012 (18)0.000 (2)0.0002 (19)
C40.023 (3)0.012 (3)0.019 (3)0.000 (2)0.008 (3)0.003 (2)
C50.022 (3)0.011 (3)0.019 (3)0.003 (2)0.007 (3)0.004 (2)
C60.022 (3)0.010 (3)0.027 (4)0.002 (2)0.010 (3)0.001 (2)
C70.014 (3)0.020 (3)0.020 (3)0.004 (2)0.002 (3)0.002 (3)
C80.014 (3)0.014 (3)0.006 (3)0.002 (2)0.003 (2)0.003 (2)
C90.015 (3)0.014 (3)0.018 (3)0.001 (2)0.007 (2)0.001 (2)
C100.022 (3)0.010 (3)0.017 (3)0.002 (2)0.006 (2)0.002 (2)
C110.017 (3)0.011 (3)0.007 (3)0.002 (2)0.002 (2)0.001 (2)
C120.013 (3)0.018 (3)0.016 (3)0.001 (2)0.005 (2)0.003 (2)
C130.016 (3)0.013 (3)0.017 (3)0.002 (2)0.000 (2)0.000 (2)
C140.011 (3)0.018 (3)0.020 (3)0.002 (2)0.005 (2)0.003 (2)
N150.012 (2)0.009 (2)0.019 (3)0.0006 (18)0.003 (2)0.0026 (19)
C160.025 (3)0.010 (3)0.018 (3)0.000 (2)0.012 (3)0.001 (2)
C170.027 (3)0.007 (3)0.021 (3)0.003 (2)0.005 (3)0.004 (2)
N180.014 (2)0.010 (2)0.020 (3)0.0005 (18)0.003 (2)0.0035 (19)
C190.018 (3)0.009 (3)0.018 (3)0.004 (2)0.009 (3)0.003 (2)
C200.021 (3)0.019 (3)0.021 (3)0.004 (2)0.007 (3)0.004 (2)
N210.010 (2)0.017 (2)0.018 (3)0.0004 (18)0.000 (2)0.001 (2)
O10.024 (2)0.013 (2)0.018 (2)0.0028 (17)0.0012 (19)0.0041 (17)
O20.050 (3)0.016 (2)0.054 (3)0.006 (2)0.012 (3)0.007 (2)
O30.025 (2)0.057 (3)0.021 (2)0.005 (2)0.002 (2)0.002 (3)
Geometric parameters (Å, º) top
Ag1—N12.165 (5)C12—H120.9500
Ag1—N18i2.173 (5)C13—C121.390 (8)
N1—C21.314 (7)C13—C81.390 (8)
N1—C51.389 (7)C13—H130.9500
C2—C61.487 (8)C14—C111.520 (7)
N3—C21.362 (7)C14—H14A0.9900
N3—C41.366 (7)C14—H14B0.9900
N3—C71.469 (7)N15—C191.367 (7)
C4—H40.9500N15—C161.377 (7)
C5—C41.345 (8)N15—C141.468 (7)
C5—H50.9500C16—H160.9500
C6—H6B0.9800C17—C161.346 (8)
C6—H6C0.9800C17—H170.9500
C6—H6A0.9800N18—C191.325 (7)
C7—C81.513 (7)N18—C171.385 (7)
C7—H7B0.9900N18—Ag1ii2.173 (5)
C7—H7A0.9900C19—C201.490 (8)
C8—C91.380 (8)C20—H20B0.9800
C9—H90.9500C20—H20A0.9800
C10—C111.384 (8)C20—H20C0.9800
C10—C91.385 (8)N21—O11.253 (6)
C10—H100.9500N21—O21.239 (6)
C11—C121.387 (8)N21—O31.236 (6)
N1—Ag1—N18i155.78 (17)C10—C11—C14119.8 (5)
C2—N1—C5106.2 (5)C12—C11—C14121.2 (5)
C2—N1—Ag1127.9 (4)C11—C12—C13120.2 (5)
C5—N1—Ag1125.9 (4)C11—C12—H12119.9
N1—C2—N3110.3 (5)C13—C12—H12119.9
N1—C2—C6125.4 (5)C12—C13—C8120.7 (5)
N3—C2—C6124.3 (5)C12—C13—H13119.6
C2—N3—C4107.5 (5)C8—C13—H13119.6
C2—N3—C7127.5 (5)N15—C14—C11112.0 (4)
C4—N3—C7124.9 (5)N15—C14—H14A109.2
C5—C4—N3106.6 (5)C11—C14—H14A109.2
C5—C4—H4126.7N15—C14—H14B109.2
N3—C4—H4126.7C11—C14—H14B109.2
C4—C5—N1109.3 (5)H14A—C14—H14B107.9
C4—C5—H5125.3C19—N15—C16107.6 (5)
N1—C5—H5125.3C19—N15—C14127.2 (5)
C2—C6—H6B109.5C16—N15—C14125.2 (5)
C2—C6—H6C109.5C17—C16—N15106.2 (5)
H6B—C6—H6C109.5C17—C16—H16126.9
C2—C6—H6A109.5N15—C16—H16126.9
H6B—C6—H6A109.5C16—C17—N18110.1 (5)
H6C—C6—H6A109.5C16—C17—H17124.9
N3—C7—C8113.1 (5)N18—C17—H17124.9
N3—C7—H7B109.0C19—N18—C17106.0 (5)
C8—C7—H7B109.0C19—N18—Ag1ii128.6 (4)
N3—C7—H7A109.0C17—N18—Ag1ii125.4 (4)
C8—C7—H7A109.0N18—C19—N15110.1 (5)
H7B—C7—H7A107.8N18—C19—C20125.3 (5)
C9—C8—C13118.7 (5)N15—C19—C20124.7 (5)
C9—C8—C7121.4 (5)C19—C20—H20B109.5
C13—C8—C7119.9 (5)C19—C20—H20A109.5
C8—C9—C10120.8 (5)H20B—C20—H20A109.5
C8—C9—H9119.6C19—C20—H20C109.5
C10—C9—H9119.6H20B—C20—H20C109.5
C11—C10—C9120.6 (5)H20A—C20—H20C109.5
C11—C10—H10119.7O3—N21—O2120.8 (5)
C9—C10—H10119.7O3—N21—O1119.8 (5)
C10—C11—C12119.0 (5)O2—N21—O1119.5 (5)
N18i—Ag1—N1—C2108.3 (6)Ag1ii—N18—C19—C202.4 (8)
N18i—Ag1—N1—C568.9 (7)C16—N15—C19—N181.3 (6)
C19—N18—C17—C160.9 (6)C14—N15—C19—N18179.2 (5)
Ag1ii—N18—C17—C16177.0 (4)C16—N15—C19—C20179.8 (5)
C2—N1—C5—C40.2 (6)C14—N15—C19—C202.0 (8)
Ag1—N1—C5—C4177.9 (4)N18—C17—C16—N150.1 (6)
C2—N3—C7—C898.9 (6)C19—N15—C16—C170.7 (6)
C4—N3—C7—C878.7 (7)C14—N15—C16—C17178.6 (5)
C12—C13—C8—C90.0 (8)N1—C5—C4—N30.6 (6)
C12—C13—C8—C7178.1 (5)C2—N3—C4—C50.8 (6)
N3—C7—C8—C963.6 (7)C7—N3—C4—C5178.8 (5)
N3—C7—C8—C13118.3 (6)C19—N15—C14—C11100.9 (6)
C5—N1—C2—N30.3 (6)C16—N15—C14—C1176.5 (7)
Ag1—N1—C2—N3177.3 (3)C9—C10—C11—C121.1 (8)
C5—N1—C2—C6179.5 (5)C9—C10—C11—C14178.8 (5)
Ag1—N1—C2—C62.9 (8)N15—C14—C11—C10119.7 (6)
C4—N3—C2—N10.7 (6)N15—C14—C11—C1260.5 (7)
C7—N3—C2—N1178.6 (5)C10—C11—C12—C131.0 (8)
C4—N3—C2—C6179.1 (5)C14—C11—C12—C13178.9 (5)
C7—N3—C2—C61.2 (8)C8—C13—C12—C110.5 (8)
C17—N18—C19—N151.4 (6)C13—C8—C9—C100.1 (8)
Ag1ii—N18—C19—N15176.5 (3)C7—C8—C9—C10178.0 (5)
C17—N18—C19—C20179.8 (5)C11—C10—C9—C80.7 (9)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x1, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O2iii0.952.643.387 (7)136
C14—H14b···O2iii0.993.173.886 (8)130
C13—H13···O2iv0.952.663.404 (8)135
C7—H7b···O2iv0.993.073.778 (8)129
Symmetry codes: (iii) x, y+1, z; (iv) x, y1/2, z+1/2.
 

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