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The title compound, (C16H20N4)3[AgCl4]2, exists as discrete 3,3′-(1,4-phenyl­dimethyl­ene)bis(1-methyl­imidazol­ium) cations and tetrachloroargentate(I) anions, which are linked by C—H...Cl hydrogen bonds [C...Cl = 3.453 (5)–3.711 (7) Å] and π–π interactions. The asymmetric unit contains one anion, one cation in a general position, and half of a cation which lies on an inversion centre.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001583/ci6513sup1.cif
Contains datablocks 030508d, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001583/ci6513Isup2.hkl
Contains datablock I

CCDC reference: 263573

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.051
  • wR factor = 0.132
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.42 PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

3,3'-(p-phenylenedimethylene)bis(1-methylimiadzolium)–tetrachloroargentate(I) (3/2) top
Crystal data top
(C16H20N4)3[AgCl4]2F(000) = 1324
Mr = 1304.42Dx = 1.521 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 962 reflections
a = 9.111 (3) Åθ = 3.3–24.0°
b = 18.921 (7) ŵ = 1.11 mm1
c = 16.536 (5) ÅT = 293 K
β = 92.368 (6)°Block, colourless
V = 2848.2 (17) Å30.24 × 0.20 × 0.16 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
5799 independent reflections
Radiation source: fine-focus sealed tube3614 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1110
Tmin = 0.689, Tmax = 0.838k = 2223
13029 measured reflectionsl = 2011
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.048P)2 + 2.3376P]
where P = (Fo2 + 2Fc2)/3
5799 reflections(Δ/σ)max < 0.001
319 parametersΔρmax = 0.97 e Å3
0 restraintsΔρmin = 0.40 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
Ag10.77042 (4)0.19654 (3)0.20540 (3)0.07001 (18)
Cl10.99882 (13)0.15684 (8)0.28615 (8)0.0618 (3)
Cl20.5975 (2)0.25556 (13)0.30595 (9)0.1188 (8)
Cl30.81265 (15)0.29222 (8)0.09801 (9)0.0735 (4)
Cl40.66917 (16)0.08514 (9)0.13128 (10)0.0830 (5)
N10.9620 (4)0.1050 (2)0.9995 (2)0.0519 (10)
N20.7947 (4)0.0797 (2)0.9076 (2)0.0517 (10)
N30.7871 (4)0.22876 (19)0.6280 (2)0.0452 (9)
N40.9034 (4)0.2563 (2)0.5216 (2)0.0507 (9)
N50.4477 (5)0.0685 (3)0.3880 (2)0.0670 (13)
N60.6511 (4)0.0124 (2)0.3714 (2)0.0472 (9)
C11.0988 (6)0.1325 (3)1.0392 (3)0.0741 (16)
H1A1.08130.17881.06030.111*
H1B1.12960.10151.08270.111*
H1C1.17420.13481.00040.111*
C20.9276 (5)0.1071 (2)0.9212 (3)0.0489 (11)
H20.98720.12490.88170.059*
C30.8478 (7)0.0740 (3)1.0372 (3)0.0768 (17)
H30.84320.06501.09230.092*
C40.7435 (7)0.0589 (3)0.9801 (4)0.0804 (19)
H40.65300.03800.98850.096*
C50.7167 (5)0.0716 (3)0.8278 (3)0.0572 (13)
H5A0.61480.08530.83240.069*
H5B0.76030.10300.78920.069*
C60.7232 (5)0.0035 (2)0.7966 (3)0.0476 (11)
C70.8502 (5)0.0279 (3)0.7609 (3)0.0518 (12)
H70.92960.00240.75540.062*
C80.8585 (5)0.0969 (3)0.7338 (3)0.0516 (12)
H80.94440.11300.71140.062*
C90.7399 (5)0.1424 (2)0.7396 (3)0.0457 (11)
C100.6135 (5)0.1183 (3)0.7740 (3)0.0513 (12)
H100.53330.14830.77770.062*
C110.6053 (5)0.0498 (3)0.8029 (3)0.0510 (12)
H110.52020.03460.82680.061*
C120.7508 (6)0.2186 (3)0.7134 (3)0.0634 (14)
H12A0.65790.24180.72230.076*
H12B0.82540.24190.74750.076*
C130.9154 (5)0.2500 (3)0.6009 (3)0.0493 (11)
H130.99980.25900.63290.059*
C140.6907 (5)0.2219 (3)0.5623 (4)0.0623 (14)
H140.59290.20800.56350.075*
C150.7626 (6)0.2386 (3)0.4967 (3)0.0638 (14)
H150.72450.23840.44360.077*
C161.0185 (7)0.2804 (4)0.4689 (3)0.0834 (18)
H16A1.02240.33110.46940.125*
H16B0.99710.26420.41470.125*
H16C1.11150.26170.48810.125*
C170.3399 (7)0.1272 (4)0.3932 (4)0.103 (3)
H17A0.32720.13880.44900.155*
H17B0.24740.11270.36860.155*
H17C0.37560.16780.36540.155*
C180.5868 (5)0.0760 (3)0.3673 (3)0.0562 (13)
H180.63130.11800.35260.067*
C190.4221 (6)0.0003 (4)0.4049 (3)0.0705 (17)
H190.33360.01870.42070.085*
C200.5487 (5)0.0360 (3)0.3946 (3)0.0595 (13)
H200.56320.08430.40190.071*
C210.8057 (5)0.0030 (3)0.3545 (3)0.0528 (12)
H21A0.84010.03150.31620.063*
H21B0.81140.04930.32970.063*
C220.9060 (4)0.0014 (2)0.4306 (3)0.0441 (11)
C230.9503 (5)0.0624 (3)0.4656 (3)0.0528 (12)
H230.91700.10460.44260.063*
C241.0430 (5)0.0641 (3)0.5338 (3)0.0534 (12)
H241.07150.10730.55620.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0593 (2)0.0896 (4)0.0610 (3)0.0224 (2)0.00078 (18)0.0098 (2)
Cl10.0484 (6)0.0734 (9)0.0630 (8)0.0091 (6)0.0074 (5)0.0159 (7)
Cl20.1241 (15)0.182 (2)0.0500 (9)0.1001 (15)0.0013 (8)0.0013 (10)
Cl30.0637 (8)0.0668 (9)0.0896 (10)0.0001 (7)0.0002 (7)0.0261 (7)
Cl40.0732 (9)0.0768 (10)0.1007 (12)0.0214 (8)0.0226 (8)0.0090 (9)
N10.065 (2)0.052 (3)0.039 (2)0.005 (2)0.0081 (19)0.0007 (18)
N20.061 (2)0.047 (2)0.048 (2)0.0028 (19)0.0142 (19)0.0090 (18)
N30.048 (2)0.040 (2)0.047 (2)0.0004 (17)0.0025 (17)0.0009 (17)
N40.056 (2)0.049 (2)0.046 (2)0.0019 (19)0.0035 (18)0.0057 (18)
N50.050 (2)0.105 (4)0.045 (2)0.029 (3)0.0119 (19)0.016 (2)
N60.043 (2)0.056 (3)0.043 (2)0.0068 (19)0.0067 (16)0.0033 (18)
C10.068 (3)0.094 (5)0.059 (3)0.003 (3)0.004 (3)0.005 (3)
C20.060 (3)0.045 (3)0.043 (3)0.001 (2)0.013 (2)0.002 (2)
C30.109 (5)0.077 (4)0.045 (3)0.016 (4)0.022 (3)0.002 (3)
C40.094 (4)0.087 (5)0.063 (4)0.035 (4)0.036 (3)0.015 (3)
C50.060 (3)0.056 (3)0.056 (3)0.003 (2)0.001 (2)0.006 (2)
C60.049 (2)0.051 (3)0.043 (3)0.002 (2)0.003 (2)0.000 (2)
C70.044 (2)0.054 (3)0.058 (3)0.009 (2)0.010 (2)0.004 (2)
C80.047 (3)0.052 (3)0.057 (3)0.002 (2)0.014 (2)0.001 (2)
C90.056 (3)0.043 (3)0.039 (2)0.000 (2)0.004 (2)0.003 (2)
C100.048 (3)0.058 (3)0.048 (3)0.012 (2)0.005 (2)0.001 (2)
C110.040 (2)0.066 (3)0.047 (3)0.000 (2)0.006 (2)0.004 (2)
C120.082 (4)0.047 (3)0.062 (3)0.005 (3)0.016 (3)0.008 (2)
C130.046 (3)0.051 (3)0.049 (3)0.005 (2)0.010 (2)0.003 (2)
C140.046 (3)0.054 (3)0.084 (4)0.003 (2)0.024 (3)0.006 (3)
C150.072 (3)0.059 (3)0.057 (3)0.006 (3)0.029 (3)0.008 (3)
C160.089 (4)0.098 (5)0.064 (4)0.010 (4)0.020 (3)0.011 (3)
C170.076 (4)0.158 (7)0.074 (4)0.073 (4)0.010 (3)0.017 (4)
C180.051 (3)0.066 (4)0.050 (3)0.012 (2)0.011 (2)0.004 (2)
C190.042 (3)0.118 (6)0.051 (3)0.001 (3)0.003 (2)0.013 (3)
C200.055 (3)0.074 (4)0.048 (3)0.002 (3)0.009 (2)0.009 (3)
C210.042 (2)0.070 (3)0.046 (3)0.013 (2)0.000 (2)0.004 (2)
C220.032 (2)0.053 (3)0.048 (3)0.004 (2)0.0069 (18)0.001 (2)
C230.055 (3)0.040 (3)0.062 (3)0.008 (2)0.006 (2)0.007 (2)
C240.051 (3)0.048 (3)0.060 (3)0.003 (2)0.000 (2)0.003 (2)
Geometric parameters (Å, º) top
Ag1—Cl12.539 (1)C7—C81.383 (7)
Ag1—Cl32.576 (2)C7—H70.93
Ag1—Cl42.589 (2)C8—C91.388 (6)
Ag1—Cl22.591 (2)C8—H80.93
N1—C21.320 (5)C9—C101.382 (6)
N1—C31.367 (7)C9—C121.511 (7)
N1—C11.479 (6)C10—C111.383 (7)
N2—C21.327 (6)C10—H100.93
N2—C41.362 (6)C11—H110.93
N2—C51.482 (6)C12—H12A0.97
N3—C131.331 (6)C12—H12B0.97
N3—C141.375 (6)C13—H130.93
N3—C121.475 (6)C14—C151.328 (7)
N4—C131.318 (5)C14—H140.93
N4—C151.372 (6)C15—H150.93
N4—C161.463 (6)C16—H16A0.96
N5—C181.334 (6)C16—H16B0.96
N5—C191.344 (8)C16—H16C0.96
N5—C171.486 (7)C17—H17A0.96
N6—C181.339 (6)C17—H17B0.96
N6—C201.373 (6)C17—H17C0.96
N6—C211.476 (5)C18—H180.93
C1—H1A0.96C19—C201.359 (7)
C1—H1B0.96C19—H190.93
C1—H1C0.96C20—H200.93
C2—H20.93C21—C221.524 (6)
C3—C41.341 (8)C21—H21A0.97
C3—H30.93C21—H21B0.97
C4—H40.93C22—C231.391 (6)
C5—C61.514 (7)C22—C24i1.396 (6)
C5—H5A0.97C23—C241.382 (6)
C5—H5B0.97C23—H230.93
C6—C111.394 (6)C24—C22i1.396 (6)
C6—C71.399 (6)C24—H240.93
Cl1—Ag1—Cl3115.34 (5)C9—C10—C11120.6 (4)
Cl1—Ag1—Cl4106.04 (6)C9—C10—H10119.7
Cl1—Ag1—Cl2107.27 (5)C11—C10—H10119.7
Cl3—Ag1—Cl4107.83 (6)C10—C11—C6120.7 (4)
Cl3—Ag1—Cl2104.58 (7)C10—C11—H11119.7
Cl4—Ag1—Cl2116.14 (7)C6—C11—H11119.7
C2—N1—C3107.8 (4)N3—C12—C9114.7 (4)
C2—N1—C1125.9 (4)N3—C12—H12A108.6
C3—N1—C1126.3 (4)C9—C12—H12A108.6
C2—N2—C4107.9 (4)N3—C12—H12B108.6
C2—N2—C5126.3 (4)C9—C12—H12B108.6
C4—N2—C5125.8 (5)H12A—C12—H12B107.6
C13—N3—C14107.7 (4)N4—C13—N3108.9 (4)
C13—N3—C12126.5 (4)N4—C13—H13125.5
C14—N3—C12125.7 (4)N3—C13—H13125.5
C13—N4—C15108.3 (4)C15—C14—N3107.6 (4)
C13—N4—C16126.0 (4)C15—C14—H14126.2
C15—N4—C16125.6 (5)N3—C14—H14126.2
C18—N5—C19109.2 (5)C14—C15—N4107.4 (4)
C18—N5—C17124.9 (6)C14—C15—H15126.3
C19—N5—C17125.8 (5)N4—C15—H15126.3
C18—N6—C20108.2 (4)N4—C16—H16A109.5
C18—N6—C21125.9 (4)N4—C16—H16B109.5
C20—N6—C21125.8 (4)H16A—C16—H16B109.5
N1—C1—H1A109.5N4—C16—H16C109.5
N1—C1—H1B109.5H16A—C16—H16C109.5
H1A—C1—H1B109.5H16B—C16—H16C109.5
N1—C1—H1C109.5N5—C17—H17A109.5
H1A—C1—H1C109.5N5—C17—H17B109.5
H1B—C1—H1C109.5H17A—C17—H17B109.5
N1—C2—N2109.4 (4)N5—C17—H17C109.5
N1—C2—H2125.3H17A—C17—H17C109.5
N2—C2—H2125.3H17B—C17—H17C109.5
C4—C3—N1107.5 (5)N5—C18—N6108.1 (5)
C4—C3—H3126.2N5—C18—H18125.9
N1—C3—H3126.2N6—C18—H18125.9
C3—C4—N2107.4 (5)N5—C19—C20107.7 (5)
C3—C4—H4126.3N5—C19—H19126.1
N2—C4—H4126.3C20—C19—H19126.1
N2—C5—C6112.1 (4)C19—C20—N6106.7 (5)
N2—C5—H5A109.2C19—C20—H20126.6
C6—C5—H5A109.2N6—C20—H20126.6
N2—C5—H5B109.2N6—C21—C22112.6 (4)
C6—C5—H5B109.2N6—C21—H21A109.1
H5A—C5—H5B107.9C22—C21—H21A109.1
C11—C6—C7118.5 (4)N6—C21—H21B109.1
C11—C6—C5121.6 (4)C22—C21—H21B109.1
C7—C6—C5119.9 (4)H21A—C21—H21B107.8
C8—C7—C6120.4 (4)C23—C22—C24i118.4 (4)
C8—C7—H7119.8C23—C22—C21121.0 (4)
C6—C7—H7119.8C24i—C22—C21120.6 (4)
C7—C8—C9120.6 (4)C24—C23—C22121.1 (4)
C7—C8—H8119.7C24—C23—H23119.4
C9—C8—H8119.7C22—C23—H23119.4
C10—C9—C8119.2 (4)C23—C24—C22i120.5 (4)
C10—C9—C12119.9 (4)C23—C24—H24119.8
C8—C9—C12120.7 (4)C22i—C24—H24119.8
C3—N1—C2—N21.1 (6)C8—C9—C12—N358.7 (6)
C1—N1—C2—N2178.0 (5)C15—N4—C13—N30.1 (5)
C4—N2—C2—N10.6 (6)C16—N4—C13—N3178.1 (5)
C5—N2—C2—N1179.3 (4)C14—N3—C13—N40.3 (5)
C2—N1—C3—C41.2 (6)C12—N3—C13—N4176.8 (4)
C1—N1—C3—C4177.9 (5)C13—N3—C14—C150.4 (6)
N1—C3—C4—N20.8 (7)C12—N3—C14—C15176.9 (4)
C2—N2—C4—C30.2 (7)N3—C14—C15—N40.3 (6)
C5—N2—C4—C3178.6 (5)C13—N4—C15—C140.1 (6)
C2—N2—C5—C6101.8 (5)C16—N4—C15—C14177.8 (5)
C4—N2—C5—C676.8 (6)C19—N5—C18—N60.4 (5)
N2—C5—C6—C11100.5 (5)C17—N5—C18—N6178.3 (4)
N2—C5—C6—C779.1 (6)C20—N6—C18—N50.5 (5)
C11—C6—C7—C81.0 (7)C21—N6—C18—N5179.0 (4)
C5—C6—C7—C8178.6 (4)C18—N5—C19—C200.1 (6)
C6—C7—C8—C91.6 (7)C17—N5—C19—C20178.6 (4)
C7—C8—C9—C100.9 (7)N5—C19—C20—N60.2 (5)
C7—C8—C9—C12177.3 (5)C18—N6—C20—C190.5 (5)
C8—C9—C10—C110.5 (7)C21—N6—C20—C19179.1 (4)
C12—C9—C10—C11175.9 (4)C18—N6—C21—C2293.4 (5)
C9—C10—C11—C61.2 (7)C20—N6—C21—C2286.1 (5)
C7—C6—C11—C100.4 (7)N6—C21—C22—C2376.5 (6)
C5—C6—C11—C10180.0 (4)N6—C21—C22—C24i104.3 (5)
C13—N3—C12—C9106.3 (5)C24i—C22—C23—C240.2 (8)
C14—N3—C12—C977.8 (6)C21—C22—C23—C24179.0 (4)
C10—C9—C12—N3124.9 (5)C22—C23—C24—C22i0.2 (8)
Symmetry code: (i) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1C···Cl4i0.962.813.703 (6)154
C5—H5A···Cl4ii0.972.683.617 (5)162
C5—H5B···Cl1i0.972.763.643 (5)151
C12—H12A···Cl1iii0.972.653.536 (6)152
C12—H12B···Cl2iv0.972.623.487 (6)148
C14—H14···Cl3iii0.932.643.529 (5)160
C15—H15···Cl20.932.533.453 (5)171
C16—H16C···Cl3iv0.962.733.627 (6)157
C17—H17A···Cl3iii0.962.803.732 (7)165
C17—H17B···Cl1v0.962.733.557 (7)145
C17—H17C···Cl20.962.823.711 (7)154
C18—H18···Cl20.932.733.548 (6)148
C20—H20···Cl3vi0.932.603.487 (6)161
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1; (iii) x1/2, y+1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2; (v) x1, y, z; (vi) x+3/2, y1/2, z+1/2.
 

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