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The reaction of 3,4,5,6-tetrahydropyrimidine-2-thione (H4pymtH) with mercury(II) iodide in methanol in a 1:1 molar ratio resulted in the formation of single crystals of the title compound, [Hg(C4H8N2S)I2]. The Hg atom is coordinated by one S atom from H4pymtH at 2.456 (2) Å and by two I atoms at distances of 2.6872 (7) and 2.7044 (6) Å, and has a characteristic deformed trigonal coordination geometry. The molecule has crystallographic m symmetry but the Hg atom is disordered above and below the mirror plane.
Supporting information
CCDC references: 142803; 163905
Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1990); software used to prepare material for publication: SHELXL97.
diiodo-3,4,5,6-tetrahydropyrimidinium-2-thiolato mercury(II)
top
Crystal data top
[Hg(C4H8N2S)I2] | Z = 4 |
Mr = 570.57 | F(000) = 992 |
Orthorhombic, Pnma | Dx = 3.492 Mg m−3 |
Hall symbol: -P 2ac 2n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.826 (2) Å | µ = 20.01 mm−1 |
b = 7.392 (1) Å | T = 200 K |
c = 11.447 (2) Å | Prism, yellow |
V = 1085.3 (4) Å3 | 0.2 × 0.1 × 0.1 mm |
Data collection top
Nonius Kappa CCD diffractometer | 1428 independent reflections |
Radiation source: fine-focus sealed tube | 1286 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 28.3°, θmin = 3.2° |
Absorption correction: semiempirical (using intensity measurements) (XEMP; Sheldrick, 1988) | h = −15→17 |
Tmin = 0.059, Tmax = 0.135 | k = −9→8 |
10676 measured reflections | l = −15→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.025 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.057 | w = 1/[σ2(Fo2) + (0.0169P)2 + 1.6028P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
1428 reflections | Δρmax = 0.66 e Å−3 |
59 parameters | Δρmin = −0.84 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00466 (19) |
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. Diffraction data were collected on a Nonius Kappa CCD diffractometer (capillary
optics) at 200 K. 188 frames were collected at the crystal-detector distance
of 35 mm, 20 s/°, 1 set of φ scans, 4 sets of ω scans, 2° per frame.
Program DENZO-SMN was used for data reduction (Otwinowski and Minor,
1997). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Hg | 0.09785 (2) | 0.2235 (4) | 0.06137 (3) | 0.0556 (5) | 0.50 |
I1 | 0.13565 (4) | 0.2500 | 0.29164 (4) | 0.04968 (15) | |
I2 | −0.09545 (3) | 0.2500 | −0.03145 (4) | 0.04647 (14) | |
S | 0.25088 (12) | 0.2500 | −0.06643 (14) | 0.0439 (3) | |
C1 | 0.1848 (4) | 0.2500 | −0.1991 (5) | 0.0348 (11) | |
N | 0.1606 (3) | 0.0979 (5) | −0.2489 (3) | 0.0542 (10) | |
H | 0.1769 | −0.0010 | −0.2137 | 0.065* | |
C2 | 0.1068 (4) | 0.0850 (9) | −0.3627 (5) | 0.0671 (15) | |
H2A | 0.0634 | −0.0223 | −0.3649 | 0.080* | |
H2B | 0.1575 | 0.0769 | −0.4254 | 0.080* | |
C3 | 0.0415 (5) | 0.2500 | −0.3776 (6) | 0.070 (2) | |
H3A | 0.0102 | 0.2500 | −0.4547 | 0.084* | |
H3B | −0.0142 | 0.2500 | −0.3202 | 0.084* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Hg | 0.04130 (18) | 0.0915 (15) | 0.03403 (17) | −0.0034 (3) | −0.00217 (10) | −0.0013 (2) |
I1 | 0.0572 (3) | 0.0607 (3) | 0.0311 (2) | 0.000 | 0.00020 (17) | 0.000 |
I2 | 0.0346 (2) | 0.0473 (2) | 0.0575 (3) | 0.000 | −0.00502 (16) | 0.000 |
S | 0.0327 (7) | 0.0602 (9) | 0.0387 (7) | 0.000 | −0.0036 (6) | 0.000 |
C1 | 0.028 (2) | 0.039 (3) | 0.037 (3) | 0.000 | 0.006 (2) | 0.000 |
N | 0.073 (3) | 0.0420 (19) | 0.048 (2) | −0.0043 (19) | −0.011 (2) | −0.0030 (17) |
C2 | 0.075 (4) | 0.077 (4) | 0.049 (3) | −0.026 (3) | −0.006 (3) | −0.011 (3) |
C3 | 0.033 (3) | 0.140 (8) | 0.036 (3) | 0.000 | 0.000 (3) | 0.000 |
Geometric parameters (Å, º) top
Hg—Hgi | 0.391 (5) | S—Hgi | 2.456 (2) |
Hg—S | 2.456 (2) | C1—N | 1.298 (5) |
Hg—I1 | 2.6872 (7) | C1—Ni | 1.298 (5) |
Hg—I2 | 2.7044 (6) | N—C2 | 1.477 (7) |
I1—Hgi | 2.6872 (7) | C2—C3 | 1.490 (7) |
I2—Hgi | 2.7044 (6) | C3—C2i | 1.490 (7) |
S—C1 | 1.740 (6) | | |
| | | |
Hgi—Hg—S | 85.43 (6) | C1—S—Hg | 97.5 (2) |
Hgi—Hg—I1 | 85.82 (6) | Hgi—S—Hg | 9.14 (12) |
S—Hg—I1 | 115.74 (4) | N—C1—Ni | 120.1 (6) |
Hgi—Hg—I2 | 85.85 (6) | N—C1—S | 120.0 (3) |
S—Hg—I2 | 119.53 (4) | Ni—C1—S | 120.0 (3) |
I1—Hg—I2 | 123.06 (2) | C1—N—C2 | 123.6 (4) |
Hg—I1—Hgi | 8.35 (11) | N—C2—C3 | 108.1 (5) |
Hg—I2—Hgi | 8.30 (11) | C2i—C3—C2 | 109.9 (6) |
C1—S—Hgi | 97.50 (18) | | |
Symmetry code: (i) x, −y+1/2, z. |
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