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The title compound, (C18H26N2S2)[HgI4], consists of a discrete tetra­iodo­mercurate(II) dianion and a bis­[4-(tri­methyl­ammonio)­phenyl] di­sulfide (Tab-Tab) dication. The geometry about the Hg atom in the dianion is a slightly distorted tetrahedral. The Tab-Tab dications are arranged parallel to each other. Three I atoms of the HgI42- dianion are connected to the adjacent H atoms of the methyl and phenyl groups of the Tab-Tab dications to form a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031630/is6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031630/is6020Isup2.hkl
Contains datablock I

CCDC reference: 262239

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.041
  • wR factor = 0.101
  • Data-to-parameter ratio = 25.7

checkCIF/PLATON results

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Alert level C PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT480_ALERT_4_C Long H...A H-Bond Reported H16A .. I4 .. 3.10 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis[4-trimethylammonio)phenyl] disulfide tetraiodomercurate(II) top
Crystal data top
(C18H26N2S2)[HgI4]F(000) = 1888
Mr = 1042.72Dx = 2.458 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 10684 reflections
a = 10.4974 (8) Åθ = 3.1–27.5°
b = 20.3856 (13) ŵ = 10.00 mm1
c = 13.2263 (10) ÅT = 193 K
β = 95.332 (2)°Block, colourless
V = 2818.1 (4) Å30.50 × 0.20 × 0.15 mm
Z = 4
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
6459 independent reflections
Radiation source: fine-focus sealed tube5645 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1313
Absorption correction: multi-scan
(Jacobson, 1998)
k = 2226
Tmin = 0.104, Tmax = 0.223l = 1716
31234 measured reflections
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0502P)2 + 3.7432P]
where P = (Fo2 + 2Fc2)/3
6445 reflections(Δ/σ)max = 0.001
251 parametersΔρmax = 2.35 e Å3
0 restraintsΔρmin = 1.93 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
Hg10.72683 (2)0.369044 (11)0.780598 (18)0.03736 (9)
I10.80511 (6)0.37933 (3)0.98471 (3)0.05633 (15)
I20.54363 (4)0.26956 (2)0.75733 (4)0.04652 (12)
I30.90480 (4)0.33591 (2)0.64392 (3)0.04460 (12)
I40.64782 (4)0.49505 (2)0.72408 (4)0.04581 (12)
S10.26890 (19)0.65959 (8)0.72510 (15)0.0513 (5)
S20.14150 (17)0.58667 (10)0.68781 (16)0.0549 (5)
N10.7272 (5)0.6380 (2)0.4836 (4)0.0360 (11)
N20.2705 (6)0.3651 (2)0.9829 (4)0.0446 (14)
C10.3977 (6)0.6480 (3)0.6485 (5)0.0352 (13)
C20.3930 (6)0.6116 (3)0.5614 (5)0.0380 (13)
H2A0.31670.58900.53830.046*
C30.4998 (6)0.6076 (3)0.5064 (5)0.0362 (13)
H3A0.49680.58170.44640.043*
C40.6099 (6)0.6413 (3)0.5395 (4)0.0312 (12)
C50.6150 (6)0.6798 (3)0.6267 (5)0.0374 (13)
H5A0.69010.70370.64880.045*
C60.5075 (7)0.6823 (3)0.6809 (5)0.0419 (15)
H6A0.50980.70790.74110.050*
C70.8376 (7)0.6118 (4)0.5521 (6)0.0545 (18)
H7A0.85540.64140.61010.082*
H7B0.91340.60870.51440.082*
H7C0.81610.56820.57660.082*
C80.7081 (8)0.5952 (4)0.3909 (5)0.0527 (18)
H8A0.69270.55000.41140.079*
H8B0.78480.59680.35400.079*
H8C0.63430.61110.34670.079*
C90.7593 (7)0.7057 (3)0.4491 (6)0.0473 (16)
H9A0.78330.73330.50850.071*
H9B0.68460.72460.40960.071*
H9C0.83090.70330.40670.071*
C100.1864 (6)0.5226 (3)0.7756 (5)0.0377 (13)
C110.0893 (7)0.4836 (3)0.8063 (5)0.0427 (15)
H11A0.00290.49190.78160.051*
C120.1180 (7)0.4326 (3)0.8727 (5)0.0439 (15)
H12A0.05130.40570.89370.053*
C130.2433 (6)0.4205 (3)0.9091 (4)0.0359 (13)
C140.3415 (6)0.4581 (3)0.8779 (5)0.0404 (14)
H14A0.42790.44920.90200.048*
C150.3115 (6)0.5096 (3)0.8100 (5)0.0401 (14)
H15A0.37810.53590.78740.048*
C160.1976 (10)0.3753 (5)1.0746 (6)0.069 (2)
H16A0.21910.41831.10460.104*
H16B0.22070.34081.12470.104*
H16C0.10550.37331.05410.104*
C170.2264 (10)0.3005 (3)0.9308 (6)0.069 (3)
H17A0.27580.29260.87260.104*
H17B0.13520.30350.90720.104*
H17C0.24000.26420.97920.104*
C180.4082 (9)0.3579 (4)1.0182 (6)0.060 (2)
H18A0.43800.39731.05570.091*
H18B0.45750.35210.95940.091*
H18C0.42000.31951.06270.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.03735 (15)0.03372 (15)0.04193 (15)0.00063 (9)0.00859 (11)0.00035 (9)
I10.0683 (4)0.0655 (3)0.0360 (2)0.0185 (2)0.0096 (2)0.0048 (2)
I20.0360 (2)0.0390 (2)0.0635 (3)0.00763 (17)0.0008 (2)0.00496 (19)
I30.0406 (3)0.0466 (3)0.0490 (2)0.00310 (17)0.0165 (2)0.00287 (18)
I40.0452 (3)0.0290 (2)0.0620 (3)0.00186 (16)0.0016 (2)0.00138 (17)
S10.0585 (12)0.0320 (9)0.0691 (12)0.0110 (7)0.0359 (10)0.0106 (7)
S20.0340 (9)0.0626 (12)0.0693 (12)0.0077 (8)0.0106 (8)0.0288 (9)
N10.031 (3)0.038 (3)0.039 (3)0.001 (2)0.007 (2)0.002 (2)
N20.068 (4)0.028 (3)0.037 (3)0.009 (2)0.002 (3)0.001 (2)
C10.038 (3)0.025 (3)0.044 (3)0.009 (2)0.014 (3)0.006 (2)
C20.031 (3)0.036 (3)0.047 (4)0.002 (2)0.003 (3)0.003 (3)
C30.034 (3)0.040 (3)0.035 (3)0.000 (3)0.005 (3)0.004 (2)
C40.030 (3)0.030 (3)0.034 (3)0.002 (2)0.004 (2)0.003 (2)
C50.035 (3)0.039 (3)0.038 (3)0.002 (3)0.002 (3)0.006 (2)
C60.055 (4)0.036 (3)0.035 (3)0.008 (3)0.005 (3)0.005 (2)
C70.035 (4)0.069 (5)0.060 (4)0.018 (3)0.008 (3)0.010 (4)
C80.054 (5)0.057 (4)0.050 (4)0.003 (3)0.018 (3)0.017 (3)
C90.040 (4)0.048 (4)0.057 (4)0.003 (3)0.015 (3)0.005 (3)
C100.038 (3)0.038 (3)0.039 (3)0.005 (3)0.014 (3)0.005 (2)
C110.035 (4)0.046 (4)0.048 (4)0.007 (3)0.008 (3)0.002 (3)
C120.046 (4)0.041 (4)0.047 (4)0.014 (3)0.012 (3)0.003 (3)
C130.046 (4)0.031 (3)0.031 (3)0.006 (3)0.005 (3)0.004 (2)
C140.037 (4)0.033 (3)0.052 (4)0.001 (3)0.009 (3)0.001 (3)
C150.036 (4)0.035 (3)0.051 (4)0.001 (3)0.013 (3)0.004 (3)
C160.085 (7)0.086 (6)0.038 (4)0.015 (5)0.010 (4)0.007 (4)
C170.107 (7)0.029 (4)0.068 (5)0.017 (4)0.017 (5)0.001 (3)
C180.072 (6)0.052 (4)0.054 (4)0.008 (4)0.008 (4)0.011 (3)
Geometric parameters (Å, º) top
Hg1—I12.7559 (6)C7—H7C0.9800
Hg1—I42.7803 (5)C8—H8A0.9800
Hg1—I22.7921 (5)C8—H8B0.9800
Hg1—I32.8003 (5)C8—H8C0.9800
S1—C11.779 (6)C9—H9A0.9800
S1—S22.030 (3)C9—H9B0.9800
S2—C101.782 (6)C9—H9C0.9800
N1—C41.496 (8)C10—C151.375 (9)
N1—C91.501 (8)C10—C111.383 (9)
N1—C71.502 (9)C11—C121.375 (9)
N1—C81.503 (8)C11—H11A0.9500
N2—C181.484 (11)C12—C131.381 (9)
N2—C131.502 (8)C12—H12A0.9500
N2—C161.507 (10)C13—C141.379 (9)
N2—C171.538 (8)C14—C151.399 (9)
C1—C21.367 (9)C14—H14A0.9500
C1—C61.382 (9)C15—H15A0.9500
C2—C31.395 (9)C16—H16A0.9800
C2—H2A0.9500C16—H16B0.9800
C3—C41.381 (8)C16—H16C0.9800
C3—H3A0.9500C17—H17A0.9800
C4—C51.391 (8)C17—H17B0.9800
C5—C61.393 (9)C17—H17C0.9800
C5—H5A0.9500C18—H18A0.9800
C6—H6A0.9500C18—H18B0.9800
C7—H7A0.9800C18—H18C0.9800
C7—H7B0.9800
I1—Hg1—I4104.325 (17)H8A—C8—H8B109.5
I1—Hg1—I2107.628 (16)N1—C8—H8C109.5
I4—Hg1—I2117.143 (16)H8A—C8—H8C109.5
I1—Hg1—I3119.647 (18)H8B—C8—H8C109.5
I4—Hg1—I3104.449 (16)N1—C9—H9A109.5
I2—Hg1—I3104.339 (16)N1—C9—H9B109.5
C1—S1—S2106.4 (2)H9A—C9—H9B109.5
C10—S2—S1104.5 (2)N1—C9—H9C109.5
C4—N1—C9109.1 (5)H9A—C9—H9C109.5
C4—N1—C7110.0 (5)H9B—C9—H9C109.5
C9—N1—C7109.2 (5)C15—C10—C11120.0 (6)
C4—N1—C8112.1 (5)C15—C10—S2122.9 (5)
C9—N1—C8107.6 (5)C11—C10—S2117.1 (5)
C7—N1—C8108.8 (6)C12—C11—C10119.9 (6)
C18—N2—C13113.6 (5)C12—C11—H11A120.1
C18—N2—C16108.3 (6)C10—C11—H11A120.1
C13—N2—C16109.8 (6)C11—C12—C13120.2 (6)
C18—N2—C17107.5 (6)C11—C12—H12A119.9
C13—N2—C17108.7 (5)C13—C12—H12A119.9
C16—N2—C17108.9 (6)C14—C13—C12120.7 (6)
C2—C1—C6120.0 (6)C14—C13—N2120.7 (6)
C2—C1—S1125.6 (5)C12—C13—N2118.6 (6)
C6—C1—S1114.4 (5)C13—C14—C15118.7 (6)
C1—C2—C3120.3 (6)C13—C14—H14A120.7
C1—C2—H2A119.9C15—C14—H14A120.7
C3—C2—H2A119.9C10—C15—C14120.5 (6)
C4—C3—C2119.6 (6)C10—C15—H15A119.7
C4—C3—H3A120.2C14—C15—H15A119.7
C2—C3—H3A120.2N2—C16—H16A109.5
C3—C4—C5120.7 (6)N2—C16—H16B109.5
C3—C4—N1121.6 (5)H16A—C16—H16B109.5
C5—C4—N1117.7 (5)N2—C16—H16C109.5
C4—C5—C6118.4 (6)H16A—C16—H16C109.5
C4—C5—H5A120.8H16B—C16—H16C109.5
C6—C5—H5A120.8N2—C17—H17A109.5
C1—C6—C5121.0 (6)N2—C17—H17B109.5
C1—C6—H6A119.5H17A—C17—H17B109.5
C5—C6—H6A119.5N2—C17—H17C109.5
N1—C7—H7A109.5H17A—C17—H17C109.5
N1—C7—H7B109.5H17B—C17—H17C109.5
H7A—C7—H7B109.5N2—C18—H18A109.5
N1—C7—H7C109.5N2—C18—H18B109.5
H7A—C7—H7C109.5H18A—C18—H18B109.5
H7B—C7—H7C109.5N2—C18—H18C109.5
N1—C8—H8A109.5H18A—C18—H18C109.5
N1—C8—H8B109.5H18B—C18—H18C109.5
C1—S1—S2—C1092.1 (3)S1—S2—C10—C1535.4 (6)
S2—S1—C1—C218.8 (6)S1—S2—C10—C11147.0 (5)
S2—S1—C1—C6164.2 (4)C15—C10—C11—C121.3 (10)
C6—C1—C2—C31.5 (9)S2—C10—C11—C12178.9 (5)
S1—C1—C2—C3178.4 (5)C10—C11—C12—C130.2 (10)
C1—C2—C3—C40.9 (9)C11—C12—C13—C141.5 (10)
C2—C3—C4—C50.6 (9)C11—C12—C13—N2179.0 (6)
C2—C3—C4—N1179.4 (5)C18—N2—C13—C141.7 (8)
C9—N1—C4—C3119.4 (6)C16—N2—C13—C14123.1 (7)
C7—N1—C4—C3120.9 (7)C17—N2—C13—C14117.9 (7)
C8—N1—C4—C30.3 (8)C18—N2—C13—C12178.7 (6)
C9—N1—C4—C560.6 (7)C16—N2—C13—C1257.4 (7)
C7—N1—C4—C559.1 (7)C17—N2—C13—C1261.7 (8)
C8—N1—C4—C5179.7 (6)C12—C13—C14—C151.2 (9)
C3—C4—C5—C61.3 (9)N2—C13—C14—C15179.3 (5)
N1—C4—C5—C6178.7 (5)C11—C10—C15—C141.6 (10)
C2—C1—C6—C50.7 (9)S2—C10—C15—C14179.1 (5)
S1—C1—C6—C5177.9 (5)C13—C14—C15—C100.3 (9)
C4—C5—C6—C10.7 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···I4i0.953.033.898 (6)152
C9—H9C···I3ii0.983.023.934 (7)155
C12—H12A···I1iii0.953.003.882 (7)155
C16—H16A···I4iv0.983.103.989 (9)151
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x1, y, z; (iv) x+1, y+1, z+2.
 

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