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The title compound (systematic name: 4-amino-2-thioxo-2,3-dihydro­pyrimidin-1-ium chloride), C4H6N3S+·Cl, has two cations and two anions in the asymmetric unit. The two cations have nearly the same structure. Both are nearly planar, the largest distance from the non-H atoms to the least-squares plane through the six-membered ring atoms being 0.010 (2) Å. Both Cl ions serve as hydrogen-bond acceptors. One thiocytosinium cation forms N—H...Cl hydrogen bonds with three Cl anions and the other one with four Cl ions, giving a sheet parallel to (101). There is also an N—H...S inter­molecular hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023445/bt6701sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023445/bt6701Isup2.hkl
Contains datablock I

CCDC reference: 282256

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.107
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

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Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.24 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.91
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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

(I) top
Crystal data top
C4H6N3S+·ClF(000) = 672
Mr = 163.63Dx = 1.553 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 52 reflections
a = 9.969 (2) Åθ = 10.4–17.3°
b = 13.8855 (18) ŵ = 0.75 mm1
c = 10.2272 (17) ÅT = 295 K
β = 98.704 (16)°Prism, colourless
V = 1399.5 (4) Å30.60 × 0.60 × 0.54 mm
Z = 8
Data collection top
Philips PW1100 updated by Stoe
diffractometer
2985 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 30.0°, θmin = 2.1°
ω–2θ scansh = 1414
Absorption correction: integration
(X-RED; Stoe & Cie, 1995)
k = 1919
Tmin = 0.734, Tmax = 0.772l = 914
7868 measured reflections5 standard reflections every 90 min
4084 independent reflections intensity decay: 13.5%
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0465P)2 + 0.5775P]
where P = (Fo2 + 2Fc2)/3
4084 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 1.04 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
Cl110.65662 (5)0.11196 (3)0.58423 (5)0.03489 (12)
Cl120.11345 (5)0.19462 (3)0.12896 (5)0.03317 (12)
S210.55184 (7)0.43488 (4)0.65306 (6)0.04652 (16)
C210.47881 (18)0.36081 (12)0.74754 (17)0.0275 (3)
N310.39775 (16)0.39372 (10)0.83449 (15)0.0268 (3)
C410.33230 (19)0.33689 (13)0.91237 (18)0.0298 (4)
C510.3497 (2)0.23587 (14)0.9049 (2)0.0353 (4)
C610.4304 (2)0.20237 (13)0.8208 (2)0.0356 (4)
N110.49212 (17)0.26343 (11)0.74432 (16)0.0320 (3)
N410.2569 (2)0.37821 (15)0.9907 (2)0.0462 (5)
S220.07889 (9)0.96708 (4)0.29048 (9)0.0769 (3)
C220.0337 (2)0.91902 (13)0.2060 (2)0.0349 (4)
N320.05179 (16)0.82203 (10)0.19994 (16)0.0300 (3)
C420.13773 (18)0.77848 (12)0.12707 (17)0.0286 (4)
C520.2155 (2)0.83810 (14)0.0543 (2)0.0326 (4)
C620.2000 (2)0.93362 (13)0.06222 (19)0.0331 (4)
N120.11114 (18)0.97273 (12)0.13647 (17)0.0342 (4)
N420.1470 (2)0.68471 (12)0.1279 (2)0.0430 (4)
H310.391 (2)0.4542 (17)0.844 (2)0.027 (5)*
H510.310 (3)0.1912 (19)0.951 (2)0.041 (6)*
H610.451 (3)0.1364 (19)0.812 (2)0.040 (6)*
H110.544 (3)0.238 (2)0.691 (2)0.048 (7)*
H4110.254 (3)0.442 (2)0.991 (3)0.061 (8)*
H4120.217 (3)0.347 (2)1.033 (3)0.050 (8)*
H320.003 (3)0.783 (2)0.250 (2)0.054 (7)*
H520.279 (3)0.8091 (19)0.002 (2)0.051 (7)*
H620.248 (2)0.9771 (16)0.020 (2)0.029 (5)*
H120.109 (2)1.028 (2)0.140 (2)0.040 (7)*
H4210.105 (3)0.649 (2)0.174 (3)0.054 (8)*
H4220.202 (3)0.659 (2)0.077 (3)0.053 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl110.0415 (3)0.0261 (2)0.0394 (2)0.00042 (17)0.01385 (19)0.00233 (17)
Cl120.0389 (2)0.02238 (19)0.0413 (2)0.00043 (16)0.01604 (19)0.00015 (16)
S210.0635 (4)0.0291 (2)0.0565 (3)0.0023 (2)0.0401 (3)0.0037 (2)
C210.0318 (9)0.0219 (7)0.0310 (8)0.0011 (6)0.0115 (7)0.0008 (6)
N310.0326 (8)0.0189 (6)0.0314 (7)0.0002 (6)0.0131 (6)0.0001 (5)
C410.0333 (9)0.0268 (8)0.0316 (9)0.0006 (7)0.0124 (7)0.0017 (6)
C510.0415 (10)0.0256 (8)0.0418 (10)0.0019 (7)0.0157 (8)0.0070 (7)
C610.0459 (11)0.0191 (8)0.0435 (10)0.0026 (7)0.0125 (8)0.0028 (7)
N110.0389 (9)0.0218 (7)0.0385 (8)0.0050 (6)0.0162 (7)0.0006 (6)
N410.0607 (13)0.0346 (9)0.0521 (11)0.0011 (8)0.0372 (10)0.0006 (8)
S220.1063 (6)0.0269 (3)0.1211 (7)0.0099 (3)0.0932 (6)0.0045 (3)
C220.0417 (10)0.0227 (8)0.0456 (11)0.0016 (7)0.0231 (9)0.0012 (7)
N320.0349 (8)0.0211 (6)0.0381 (8)0.0003 (6)0.0189 (7)0.0019 (6)
C420.0309 (9)0.0230 (7)0.0338 (9)0.0012 (6)0.0111 (7)0.0003 (6)
C520.0350 (9)0.0284 (8)0.0384 (10)0.0003 (7)0.0185 (8)0.0013 (7)
C620.0359 (10)0.0289 (9)0.0378 (10)0.0032 (7)0.0165 (8)0.0039 (7)
N120.0426 (9)0.0191 (7)0.0452 (9)0.0009 (6)0.0210 (7)0.0031 (6)
N420.0551 (11)0.0219 (7)0.0588 (12)0.0037 (7)0.0312 (10)0.0023 (7)
Geometric parameters (Å, º) top
S21—C211.6537 (17)S22—C221.6567 (19)
C21—N111.360 (2)C22—N121.351 (2)
C21—N311.368 (2)C22—N321.361 (2)
N31—C411.357 (2)N32—C421.360 (2)
N31—H310.85 (2)N32—H320.93 (3)
C41—N411.311 (2)C42—N421.305 (2)
C41—C511.417 (3)C42—C521.420 (2)
C51—C611.346 (3)C52—C621.339 (3)
C51—H510.91 (3)C52—H520.97 (3)
C61—N111.362 (2)C62—N121.364 (2)
C61—H610.95 (3)C62—H620.91 (2)
N11—H110.88 (3)N12—H120.77 (3)
N41—H4110.89 (3)N42—H4210.84 (3)
N41—H4120.76 (3)N42—H4220.89 (3)
N11—C21—N31114.68 (15)N12—C22—N32115.59 (16)
N11—C21—S21123.45 (13)N12—C22—S22122.58 (14)
N31—C21—S21121.86 (13)N32—C22—S22121.81 (14)
C41—N31—C21124.85 (15)C42—N32—C22124.32 (15)
C41—N31—H31117.1 (14)C42—N32—H32117.8 (17)
C21—N31—H31117.9 (15)C22—N32—H32117.9 (17)
N41—C41—N31118.39 (17)N42—C42—N32119.35 (17)
N41—C41—C51123.55 (17)N42—C42—C52122.75 (17)
N31—C41—C51118.05 (16)N32—C42—C52117.89 (15)
C61—C51—C41117.83 (17)C62—C52—C42117.92 (16)
C61—C51—H51116.8 (16)C62—C52—H52122.2 (16)
C41—C51—H51125.4 (16)C42—C52—H52119.9 (16)
C51—C61—N11121.15 (17)C52—C62—N12121.25 (17)
C51—C61—H61123.6 (15)C52—C62—H62123.6 (14)
N11—C61—H61115.3 (15)N12—C62—H62115.1 (14)
C21—N11—C61123.44 (16)C22—N12—C62123.00 (16)
C21—N11—H11119.2 (18)C22—N12—H12120.4 (19)
C61—N11—H11117.4 (18)C62—N12—H12116.6 (19)
C41—N41—H411117 (2)C42—N42—H421123 (2)
C41—N41—H412120 (2)C42—N42—H422116.8 (19)
H411—N41—H412123 (3)H421—N42—H422120 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···Cl110.88 (3)2.43 (3)3.2567 (18)157 (2)
N12—H12···Cl12i0.77 (3)2.32 (3)3.0822 (18)173.5 (19)
N31—H31···Cl11ii0.85 (2)2.38 (2)3.2100 (16)165.5 (19)
N32—H32···Cl12iii0.93 (3)2.20 (3)3.1270 (17)178 (3)
N41—H411···Cl11ii0.89 (3)2.68 (3)3.474 (2)150 (3)
N41—H412···Cl12iv0.77 (3)2.61 (3)3.340 (2)160 (3)
N42—H421···S22v0.84 (3)2.57 (3)3.2344 (19)137 (3)
N42—H422···Cl11vi0.89 (3)2.42 (3)3.293 (2)171 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+3/2; (iii) x, y+1/2, z+1/2; (iv) x, y, z+1; (v) x, y1/2, z+1/2; (vi) x+1, y+1/2, z+1/2.
 

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