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The title compound, C6H8N4S22+·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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201317X/ya6119sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201317X/ya6119Isup2.hkl
Contains datablock I

CCDC reference: 193778

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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).

(I) top
Crystal data top
C6H8N4S2+·2ClF(000) = 276
Mr = 271.18Dx = 1.698 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.8211 (8) ÅCell parameters from 22 reflections
b = 9.2441 (14) Åθ = 7.6–12.6°
c = 12.0228 (10) ŵ = 0.97 mm1
β = 98.224 (12)°T = 298 K
V = 530.31 (13) Å3Prismatic, orange
Z = 20.50 × 0.26 × 0.18 mm
Data collection top
Rigaku AFC-7S
diffractometer
886 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 26.0°, θmin = 2.8°
ω/2θ scansh = 05
Absorption correction: ψ scan
(North et al., 1968)
k = 011
Tmin = 0.616, Tmax = 0.840l = 1414
1163 measured reflections3 standard reflections every 150 reflections
1037 independent reflections intensity decay: 0.3%
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)] = 0.058Hydrogen site location: difference Fourier map
wR(F2) = 0.180Only 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 parametersΔρmax = 0.86 e Å3
0 restraintsΔρmin = 0.83 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
C20.4704 (10)0.2903 (5)0.3986 (4)0.0365 (11)
C40.4579 (10)0.0747 (5)0.4911 (4)0.0350 (10)
C50.2741 (11)0.1514 (6)0.5417 (4)0.0405 (11)
Cl0.9289 (2)0.12652 (12)0.21774 (9)0.0342 (4)
N30.5710 (9)0.1556 (4)0.4107 (4)0.0369 (9)
N60.5521 (11)0.3828 (5)0.3265 (4)0.0465 (11)
S10.2371 (3)0.32665 (14)0.49049 (11)0.0414 (4)
H30.706 (16)0.123 (8)0.356 (7)0.080*
H50.129 (16)0.109 (8)0.597 (7)0.080*
H6A0.483 (16)0.478 (9)0.316 (7)0.080*
H6B0.705 (17)0.344 (9)0.291 (7)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0343 (6)0.0366 (7)0.0355 (6)0.0092 (4)0.0182 (4)0.0108 (4)
S10.0433 (8)0.0378 (8)0.0441 (8)0.0059 (5)0.0095 (6)0.0019 (5)
C20.036 (2)0.036 (2)0.036 (2)0.001 (2)0.0008 (19)0.002 (2)
C40.035 (2)0.038 (3)0.033 (2)0.0012 (19)0.0065 (19)0.0004 (19)
N30.038 (2)0.036 (2)0.038 (2)0.0025 (17)0.0083 (17)0.0022 (17)
C50.042 (3)0.039 (3)0.041 (3)0.000 (2)0.009 (2)0.000 (2)
N60.050 (3)0.039 (3)0.051 (3)0.003 (2)0.009 (2)0.009 (2)
Geometric parameters (Å, º) top
S1—C21.718 (5)C4—C4i1.446 (10)
S1—C51.733 (5)C5—H51.10 (8)
C2—N31.337 (6)N3—H31.03 (8)
C2—N61.317 (7)N6—H6A0.95 (8)
N3—C41.393 (6)N6—H6B0.97 (8)
C4—C51.347 (7)
C2—S1—C590.1 (2)C4—C5—S1111.9 (4)
N6—C2—N3122.5 (5)C4—C5—H5127 (4)
N6—C2—S1125.5 (4)S1—C5—H5120 (4)
N3—C2—S1111.9 (4)C2—N3—H3117 (4)
C2—N3—C4113.8 (4)C4—N3—H3129 (4)
C5—C4—N3112.3 (5)C2—N6—H6A124 (5)
C5—C4—C4i128.7 (6)C2—N6—H6B111 (5)
N3—C4—C4i119.1 (5)H6A—N6—H6B124 (7)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···Cl1.03 (8)2.10 (8)3.094 (5)159 (6)
N6—H6A···Clii0.94 (8)2.40 (8)3.222 (5)146 (7)
N6—H6B···Cl0.97 (8)2.50 (8)3.362 (5)148 (7)
Symmetry code: (ii) x+1, y+1/2, z+1/2.
 

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