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
CCDC reference: 262239
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.009 Å
- R factor = 0.041
- wR factor = 0.101
- Data-to-parameter ratio = 25.7
checkCIF/PLATON results
No syntax errors found
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
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 = 1042.72 | Dx = 2.458 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2yn | Cell parameters from 10684 reflections |
a = 10.4974 (8) Å | θ = 3.1–27.5° |
b = 20.3856 (13) Å | µ = 10.00 mm−1 |
c = 13.2263 (10) Å | T = 193 K |
β = 95.332 (2)° | Block, colourless |
V = 2818.1 (4) Å3 | 0.50 × 0.20 × 0.15 mm |
Z = 4 | |
Data collection top
Rigaku Mercury CCD area-detector diffractometer | 6459 independent reflections |
Radiation source: fine-focus sealed tube | 5645 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −22→26 |
Tmin = 0.104, Tmax = 0.223 | l = −17→16 |
31234 measured reflections | |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-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 parameters | Δρmax = 2.35 e Å−3 |
0 restraints | Δρmin = −1.93 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 | |
Hg1 | 0.72683 (2) | 0.369044 (11) | 0.780598 (18) | 0.03736 (9) | |
I1 | 0.80511 (6) | 0.37933 (3) | 0.98471 (3) | 0.05633 (15) | |
I2 | 0.54363 (4) | 0.26956 (2) | 0.75733 (4) | 0.04652 (12) | |
I3 | 0.90480 (4) | 0.33591 (2) | 0.64392 (3) | 0.04460 (12) | |
I4 | 0.64782 (4) | 0.49505 (2) | 0.72408 (4) | 0.04581 (12) | |
S1 | 0.26890 (19) | 0.65959 (8) | 0.72510 (15) | 0.0513 (5) | |
S2 | 0.14150 (17) | 0.58667 (10) | 0.68781 (16) | 0.0549 (5) | |
N1 | 0.7272 (5) | 0.6380 (2) | 0.4836 (4) | 0.0360 (11) | |
N2 | 0.2705 (6) | 0.3651 (2) | 0.9829 (4) | 0.0446 (14) | |
C1 | 0.3977 (6) | 0.6480 (3) | 0.6485 (5) | 0.0352 (13) | |
C2 | 0.3930 (6) | 0.6116 (3) | 0.5614 (5) | 0.0380 (13) | |
H2A | 0.3167 | 0.5890 | 0.5383 | 0.046* | |
C3 | 0.4998 (6) | 0.6076 (3) | 0.5064 (5) | 0.0362 (13) | |
H3A | 0.4968 | 0.5817 | 0.4464 | 0.043* | |
C4 | 0.6099 (6) | 0.6413 (3) | 0.5395 (4) | 0.0312 (12) | |
C5 | 0.6150 (6) | 0.6798 (3) | 0.6267 (5) | 0.0374 (13) | |
H5A | 0.6901 | 0.7037 | 0.6488 | 0.045* | |
C6 | 0.5075 (7) | 0.6823 (3) | 0.6809 (5) | 0.0419 (15) | |
H6A | 0.5098 | 0.7079 | 0.7411 | 0.050* | |
C7 | 0.8376 (7) | 0.6118 (4) | 0.5521 (6) | 0.0545 (18) | |
H7A | 0.8554 | 0.6414 | 0.6101 | 0.082* | |
H7B | 0.9134 | 0.6087 | 0.5144 | 0.082* | |
H7C | 0.8161 | 0.5682 | 0.5766 | 0.082* | |
C8 | 0.7081 (8) | 0.5952 (4) | 0.3909 (5) | 0.0527 (18) | |
H8A | 0.6927 | 0.5500 | 0.4114 | 0.079* | |
H8B | 0.7848 | 0.5968 | 0.3540 | 0.079* | |
H8C | 0.6343 | 0.6111 | 0.3467 | 0.079* | |
C9 | 0.7593 (7) | 0.7057 (3) | 0.4491 (6) | 0.0473 (16) | |
H9A | 0.7833 | 0.7333 | 0.5085 | 0.071* | |
H9B | 0.6846 | 0.7246 | 0.4096 | 0.071* | |
H9C | 0.8309 | 0.7033 | 0.4067 | 0.071* | |
C10 | 0.1864 (6) | 0.5226 (3) | 0.7756 (5) | 0.0377 (13) | |
C11 | 0.0893 (7) | 0.4836 (3) | 0.8063 (5) | 0.0427 (15) | |
H11A | 0.0029 | 0.4919 | 0.7816 | 0.051* | |
C12 | 0.1180 (7) | 0.4326 (3) | 0.8727 (5) | 0.0439 (15) | |
H12A | 0.0513 | 0.4057 | 0.8937 | 0.053* | |
C13 | 0.2433 (6) | 0.4205 (3) | 0.9091 (4) | 0.0359 (13) | |
C14 | 0.3415 (6) | 0.4581 (3) | 0.8779 (5) | 0.0404 (14) | |
H14A | 0.4279 | 0.4492 | 0.9020 | 0.048* | |
C15 | 0.3115 (6) | 0.5096 (3) | 0.8100 (5) | 0.0401 (14) | |
H15A | 0.3781 | 0.5359 | 0.7874 | 0.048* | |
C16 | 0.1976 (10) | 0.3753 (5) | 1.0746 (6) | 0.069 (2) | |
H16A | 0.2191 | 0.4183 | 1.1046 | 0.104* | |
H16B | 0.2207 | 0.3408 | 1.1247 | 0.104* | |
H16C | 0.1055 | 0.3733 | 1.0541 | 0.104* | |
C17 | 0.2264 (10) | 0.3005 (3) | 0.9308 (6) | 0.069 (3) | |
H17A | 0.2758 | 0.2926 | 0.8726 | 0.104* | |
H17B | 0.1352 | 0.3035 | 0.9072 | 0.104* | |
H17C | 0.2400 | 0.2642 | 0.9792 | 0.104* | |
C18 | 0.4082 (9) | 0.3579 (4) | 1.0182 (6) | 0.060 (2) | |
H18A | 0.4380 | 0.3973 | 1.0557 | 0.091* | |
H18B | 0.4575 | 0.3521 | 0.9594 | 0.091* | |
H18C | 0.4200 | 0.3195 | 1.0627 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Hg1 | 0.03735 (15) | 0.03372 (15) | 0.04193 (15) | −0.00063 (9) | 0.00859 (11) | −0.00035 (9) |
I1 | 0.0683 (4) | 0.0655 (3) | 0.0360 (2) | −0.0185 (2) | 0.0096 (2) | −0.0048 (2) |
I2 | 0.0360 (2) | 0.0390 (2) | 0.0635 (3) | −0.00763 (17) | −0.0008 (2) | 0.00496 (19) |
I3 | 0.0406 (3) | 0.0466 (3) | 0.0490 (2) | 0.00310 (17) | 0.0165 (2) | −0.00287 (18) |
I4 | 0.0452 (3) | 0.0290 (2) | 0.0620 (3) | 0.00186 (16) | −0.0016 (2) | −0.00138 (17) |
S1 | 0.0585 (12) | 0.0320 (9) | 0.0691 (12) | 0.0110 (7) | 0.0359 (10) | 0.0106 (7) |
S2 | 0.0340 (9) | 0.0626 (12) | 0.0693 (12) | 0.0077 (8) | 0.0106 (8) | 0.0288 (9) |
N1 | 0.031 (3) | 0.038 (3) | 0.039 (3) | −0.001 (2) | 0.007 (2) | −0.002 (2) |
N2 | 0.068 (4) | 0.028 (3) | 0.037 (3) | −0.009 (2) | 0.002 (3) | −0.001 (2) |
C1 | 0.038 (3) | 0.025 (3) | 0.044 (3) | 0.009 (2) | 0.014 (3) | 0.006 (2) |
C2 | 0.031 (3) | 0.036 (3) | 0.047 (4) | −0.002 (2) | 0.003 (3) | 0.003 (3) |
C3 | 0.034 (3) | 0.040 (3) | 0.035 (3) | 0.000 (3) | 0.005 (3) | −0.004 (2) |
C4 | 0.030 (3) | 0.030 (3) | 0.034 (3) | 0.002 (2) | 0.004 (2) | 0.003 (2) |
C5 | 0.035 (3) | 0.039 (3) | 0.038 (3) | −0.002 (3) | 0.002 (3) | −0.006 (2) |
C6 | 0.055 (4) | 0.036 (3) | 0.035 (3) | 0.008 (3) | 0.005 (3) | −0.005 (2) |
C7 | 0.035 (4) | 0.069 (5) | 0.060 (4) | 0.018 (3) | 0.008 (3) | 0.010 (4) |
C8 | 0.054 (5) | 0.057 (4) | 0.050 (4) | −0.003 (3) | 0.018 (3) | −0.017 (3) |
C9 | 0.040 (4) | 0.048 (4) | 0.057 (4) | 0.003 (3) | 0.015 (3) | 0.005 (3) |
C10 | 0.038 (3) | 0.038 (3) | 0.039 (3) | 0.005 (3) | 0.014 (3) | 0.005 (2) |
C11 | 0.035 (4) | 0.046 (4) | 0.048 (4) | −0.007 (3) | 0.008 (3) | −0.002 (3) |
C12 | 0.046 (4) | 0.041 (4) | 0.047 (4) | −0.014 (3) | 0.012 (3) | 0.003 (3) |
C13 | 0.046 (4) | 0.031 (3) | 0.031 (3) | −0.006 (3) | 0.005 (3) | −0.004 (2) |
C14 | 0.037 (4) | 0.033 (3) | 0.052 (4) | 0.001 (3) | 0.009 (3) | −0.001 (3) |
C15 | 0.036 (4) | 0.035 (3) | 0.051 (4) | 0.001 (3) | 0.013 (3) | 0.004 (3) |
C16 | 0.085 (7) | 0.086 (6) | 0.038 (4) | −0.015 (5) | 0.010 (4) | 0.007 (4) |
C17 | 0.107 (7) | 0.029 (4) | 0.068 (5) | −0.017 (4) | −0.017 (5) | −0.001 (3) |
C18 | 0.072 (6) | 0.052 (4) | 0.054 (4) | −0.008 (4) | −0.008 (4) | 0.011 (3) |
Geometric parameters (Å, º) top
Hg1—I1 | 2.7559 (6) | C7—H7C | 0.9800 |
Hg1—I4 | 2.7803 (5) | C8—H8A | 0.9800 |
Hg1—I2 | 2.7921 (5) | C8—H8B | 0.9800 |
Hg1—I3 | 2.8003 (5) | C8—H8C | 0.9800 |
S1—C1 | 1.779 (6) | C9—H9A | 0.9800 |
S1—S2 | 2.030 (3) | C9—H9B | 0.9800 |
S2—C10 | 1.782 (6) | C9—H9C | 0.9800 |
N1—C4 | 1.496 (8) | C10—C15 | 1.375 (9) |
N1—C9 | 1.501 (8) | C10—C11 | 1.383 (9) |
N1—C7 | 1.502 (9) | C11—C12 | 1.375 (9) |
N1—C8 | 1.503 (8) | C11—H11A | 0.9500 |
N2—C18 | 1.484 (11) | C12—C13 | 1.381 (9) |
N2—C13 | 1.502 (8) | C12—H12A | 0.9500 |
N2—C16 | 1.507 (10) | C13—C14 | 1.379 (9) |
N2—C17 | 1.538 (8) | C14—C15 | 1.399 (9) |
C1—C2 | 1.367 (9) | C14—H14A | 0.9500 |
C1—C6 | 1.382 (9) | C15—H15A | 0.9500 |
C2—C3 | 1.395 (9) | C16—H16A | 0.9800 |
C2—H2A | 0.9500 | C16—H16B | 0.9800 |
C3—C4 | 1.381 (8) | C16—H16C | 0.9800 |
C3—H3A | 0.9500 | C17—H17A | 0.9800 |
C4—C5 | 1.391 (8) | C17—H17B | 0.9800 |
C5—C6 | 1.393 (9) | C17—H17C | 0.9800 |
C5—H5A | 0.9500 | C18—H18A | 0.9800 |
C6—H6A | 0.9500 | C18—H18B | 0.9800 |
C7—H7A | 0.9800 | C18—H18C | 0.9800 |
C7—H7B | 0.9800 | | |
| | | |
I1—Hg1—I4 | 104.325 (17) | H8A—C8—H8B | 109.5 |
I1—Hg1—I2 | 107.628 (16) | N1—C8—H8C | 109.5 |
I4—Hg1—I2 | 117.143 (16) | H8A—C8—H8C | 109.5 |
I1—Hg1—I3 | 119.647 (18) | H8B—C8—H8C | 109.5 |
I4—Hg1—I3 | 104.449 (16) | N1—C9—H9A | 109.5 |
I2—Hg1—I3 | 104.339 (16) | N1—C9—H9B | 109.5 |
C1—S1—S2 | 106.4 (2) | H9A—C9—H9B | 109.5 |
C10—S2—S1 | 104.5 (2) | N1—C9—H9C | 109.5 |
C4—N1—C9 | 109.1 (5) | H9A—C9—H9C | 109.5 |
C4—N1—C7 | 110.0 (5) | H9B—C9—H9C | 109.5 |
C9—N1—C7 | 109.2 (5) | C15—C10—C11 | 120.0 (6) |
C4—N1—C8 | 112.1 (5) | C15—C10—S2 | 122.9 (5) |
C9—N1—C8 | 107.6 (5) | C11—C10—S2 | 117.1 (5) |
C7—N1—C8 | 108.8 (6) | C12—C11—C10 | 119.9 (6) |
C18—N2—C13 | 113.6 (5) | C12—C11—H11A | 120.1 |
C18—N2—C16 | 108.3 (6) | C10—C11—H11A | 120.1 |
C13—N2—C16 | 109.8 (6) | C11—C12—C13 | 120.2 (6) |
C18—N2—C17 | 107.5 (6) | C11—C12—H12A | 119.9 |
C13—N2—C17 | 108.7 (5) | C13—C12—H12A | 119.9 |
C16—N2—C17 | 108.9 (6) | C14—C13—C12 | 120.7 (6) |
C2—C1—C6 | 120.0 (6) | C14—C13—N2 | 120.7 (6) |
C2—C1—S1 | 125.6 (5) | C12—C13—N2 | 118.6 (6) |
C6—C1—S1 | 114.4 (5) | C13—C14—C15 | 118.7 (6) |
C1—C2—C3 | 120.3 (6) | C13—C14—H14A | 120.7 |
C1—C2—H2A | 119.9 | C15—C14—H14A | 120.7 |
C3—C2—H2A | 119.9 | C10—C15—C14 | 120.5 (6) |
C4—C3—C2 | 119.6 (6) | C10—C15—H15A | 119.7 |
C4—C3—H3A | 120.2 | C14—C15—H15A | 119.7 |
C2—C3—H3A | 120.2 | N2—C16—H16A | 109.5 |
C3—C4—C5 | 120.7 (6) | N2—C16—H16B | 109.5 |
C3—C4—N1 | 121.6 (5) | H16A—C16—H16B | 109.5 |
C5—C4—N1 | 117.7 (5) | N2—C16—H16C | 109.5 |
C4—C5—C6 | 118.4 (6) | H16A—C16—H16C | 109.5 |
C4—C5—H5A | 120.8 | H16B—C16—H16C | 109.5 |
C6—C5—H5A | 120.8 | N2—C17—H17A | 109.5 |
C1—C6—C5 | 121.0 (6) | N2—C17—H17B | 109.5 |
C1—C6—H6A | 119.5 | H17A—C17—H17B | 109.5 |
C5—C6—H6A | 119.5 | N2—C17—H17C | 109.5 |
N1—C7—H7A | 109.5 | H17A—C17—H17C | 109.5 |
N1—C7—H7B | 109.5 | H17B—C17—H17C | 109.5 |
H7A—C7—H7B | 109.5 | N2—C18—H18A | 109.5 |
N1—C7—H7C | 109.5 | N2—C18—H18B | 109.5 |
H7A—C7—H7C | 109.5 | H18A—C18—H18B | 109.5 |
H7B—C7—H7C | 109.5 | N2—C18—H18C | 109.5 |
N1—C8—H8A | 109.5 | H18A—C18—H18C | 109.5 |
N1—C8—H8B | 109.5 | H18B—C18—H18C | 109.5 |
| | | |
C1—S1—S2—C10 | 92.1 (3) | S1—S2—C10—C15 | −35.4 (6) |
S2—S1—C1—C2 | 18.8 (6) | S1—S2—C10—C11 | 147.0 (5) |
S2—S1—C1—C6 | −164.2 (4) | C15—C10—C11—C12 | 1.3 (10) |
C6—C1—C2—C3 | 1.5 (9) | S2—C10—C11—C12 | 178.9 (5) |
S1—C1—C2—C3 | 178.4 (5) | C10—C11—C12—C13 | 0.2 (10) |
C1—C2—C3—C4 | −0.9 (9) | C11—C12—C13—C14 | −1.5 (10) |
C2—C3—C4—C5 | −0.6 (9) | C11—C12—C13—N2 | 179.0 (6) |
C2—C3—C4—N1 | 179.4 (5) | C18—N2—C13—C14 | 1.7 (8) |
C9—N1—C4—C3 | 119.4 (6) | C16—N2—C13—C14 | 123.1 (7) |
C7—N1—C4—C3 | −120.9 (7) | C17—N2—C13—C14 | −117.9 (7) |
C8—N1—C4—C3 | 0.3 (8) | C18—N2—C13—C12 | −178.7 (6) |
C9—N1—C4—C5 | −60.6 (7) | C16—N2—C13—C12 | −57.4 (7) |
C7—N1—C4—C5 | 59.1 (7) | C17—N2—C13—C12 | 61.7 (8) |
C8—N1—C4—C5 | −179.7 (6) | C12—C13—C14—C15 | 1.2 (9) |
C3—C4—C5—C6 | 1.3 (9) | N2—C13—C14—C15 | −179.3 (5) |
N1—C4—C5—C6 | −178.7 (5) | C11—C10—C15—C14 | −1.6 (10) |
C2—C1—C6—C5 | −0.7 (9) | S2—C10—C15—C14 | −179.1 (5) |
S1—C1—C6—C5 | −177.9 (5) | C13—C14—C15—C10 | 0.3 (9) |
C4—C5—C6—C1 | −0.7 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···I4i | 0.95 | 3.03 | 3.898 (6) | 152 |
C9—H9C···I3ii | 0.98 | 3.02 | 3.934 (7) | 155 |
C12—H12A···I1iii | 0.95 | 3.00 | 3.882 (7) | 155 |
C16—H16A···I4iv | 0.98 | 3.10 | 3.989 (9) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+2. |