The title compound, C
6H
8N
4S
22+·2Cl
−, includes a
trans, planar bithiazole moiety occupying a special position on a crystallographic inversion centre. Both symmetry-independent N atoms participate in hydrogen-bonded links with the chloride anion [N
Cl 3.094 (5), 3.222 (5) and 3.362 (5) Å]. A short contact of 3.3201 (18) Å is also observed between the S atom of the thiazolium cation and the chloride anion.
Supporting information
CCDC reference: 193778
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.058
- wR factor = 0.180
- Data-to-parameter ratio = 13.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_353 Alert C Long N-H Bond (0.87A) N(3) - H(3) = 1.03 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994).
Crystal data top
C6H8N4S2+·2Cl− | F(000) = 276 |
Mr = 271.18 | Dx = 1.698 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.8211 (8) Å | Cell parameters from 22 reflections |
b = 9.2441 (14) Å | θ = 7.6–12.6° |
c = 12.0228 (10) Å | µ = 0.97 mm−1 |
β = 98.224 (12)° | T = 298 K |
V = 530.31 (13) Å3 | Prismatic, orange |
Z = 2 | 0.50 × 0.26 × 0.18 mm |
Data collection top
Rigaku AFC-7S diffractometer | 886 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.049 |
Graphite monochromator | θmax = 26.0°, θmin = 2.8° |
ω/2θ scans | h = 0→5 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.616, Tmax = 0.840 | l = −14→14 |
1163 measured reflections | 3 standard reflections every 150 reflections |
1037 independent reflections | intensity decay: 0.3% |
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)] = 0.058 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.180 | Only H-atom coordinates refined |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0944P)2 + 1.6P] where P = (Fo2 + 2Fc2)/3 |
1037 reflections | (Δ/σ)max < 0.001 |
76 parameters | Δρmax = 0.86 e Å−3 |
0 restraints | Δρmin = −0.83 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 | |
C2 | 0.4704 (10) | 0.2903 (5) | 0.3986 (4) | 0.0365 (11) | |
C4 | 0.4579 (10) | 0.0747 (5) | 0.4911 (4) | 0.0350 (10) | |
C5 | 0.2741 (11) | 0.1514 (6) | 0.5417 (4) | 0.0405 (11) | |
Cl | 0.9289 (2) | 0.12652 (12) | 0.21774 (9) | 0.0342 (4) | |
N3 | 0.5710 (9) | 0.1556 (4) | 0.4107 (4) | 0.0369 (9) | |
N6 | 0.5521 (11) | 0.3828 (5) | 0.3265 (4) | 0.0465 (11) | |
S1 | 0.2371 (3) | 0.32665 (14) | 0.49049 (11) | 0.0414 (4) | |
H3 | 0.706 (16) | 0.123 (8) | 0.356 (7) | 0.080* | |
H5 | 0.129 (16) | 0.109 (8) | 0.597 (7) | 0.080* | |
H6A | 0.483 (16) | 0.478 (9) | 0.316 (7) | 0.080* | |
H6B | 0.705 (17) | 0.344 (9) | 0.291 (7) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0343 (6) | 0.0366 (7) | 0.0355 (6) | −0.0092 (4) | 0.0182 (4) | −0.0108 (4) |
S1 | 0.0433 (8) | 0.0378 (8) | 0.0441 (8) | 0.0059 (5) | 0.0095 (6) | −0.0019 (5) |
C2 | 0.036 (2) | 0.036 (2) | 0.036 (2) | −0.001 (2) | 0.0008 (19) | 0.002 (2) |
C4 | 0.035 (2) | 0.038 (3) | 0.033 (2) | 0.0012 (19) | 0.0065 (19) | 0.0004 (19) |
N3 | 0.038 (2) | 0.036 (2) | 0.038 (2) | 0.0025 (17) | 0.0083 (17) | 0.0022 (17) |
C5 | 0.042 (3) | 0.039 (3) | 0.041 (3) | 0.000 (2) | 0.009 (2) | 0.000 (2) |
N6 | 0.050 (3) | 0.039 (3) | 0.051 (3) | 0.003 (2) | 0.009 (2) | 0.009 (2) |
Geometric parameters (Å, º) top
S1—C2 | 1.718 (5) | C4—C4i | 1.446 (10) |
S1—C5 | 1.733 (5) | C5—H5 | 1.10 (8) |
C2—N3 | 1.337 (6) | N3—H3 | 1.03 (8) |
C2—N6 | 1.317 (7) | N6—H6A | 0.95 (8) |
N3—C4 | 1.393 (6) | N6—H6B | 0.97 (8) |
C4—C5 | 1.347 (7) | | |
| | | |
C2—S1—C5 | 90.1 (2) | C4—C5—S1 | 111.9 (4) |
N6—C2—N3 | 122.5 (5) | C4—C5—H5 | 127 (4) |
N6—C2—S1 | 125.5 (4) | S1—C5—H5 | 120 (4) |
N3—C2—S1 | 111.9 (4) | C2—N3—H3 | 117 (4) |
C2—N3—C4 | 113.8 (4) | C4—N3—H3 | 129 (4) |
C5—C4—N3 | 112.3 (5) | C2—N6—H6A | 124 (5) |
C5—C4—C4i | 128.7 (6) | C2—N6—H6B | 111 (5) |
N3—C4—C4i | 119.1 (5) | H6A—N6—H6B | 124 (7) |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···Cl | 1.03 (8) | 2.10 (8) | 3.094 (5) | 159 (6) |
N6—H6A···Clii | 0.94 (8) | 2.40 (8) | 3.222 (5) | 146 (7) |
N6—H6B···Cl | 0.97 (8) | 2.50 (8) | 3.362 (5) | 148 (7) |
Symmetry code: (ii) −x+1, y+1/2, −z+1/2. |