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The title compound (systematic name: 4-amino-2-thioxo-2,3-dihydropyrimidin-1-ium chloride), C
4H
6N
3S
+·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
CCDC reference: 282256
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.107
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
No syntax errors found
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
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.
Crystal data top
C4H6N3S+·Cl− | F(000) = 672 |
Mr = 163.63 | Dx = 1.553 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 52 reflections |
a = 9.969 (2) Å | θ = 10.4–17.3° |
b = 13.8855 (18) Å | µ = 0.75 mm−1 |
c = 10.2272 (17) Å | T = 295 K |
β = 98.704 (16)° | Prism, colourless |
V = 1399.5 (4) Å3 | 0.60 × 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 tube | Rint = 0.042 |
Graphite monochromator | θmax = 30.0°, θmin = 2.1° |
ω–2θ scans | h = −14→14 |
Absorption correction: integration (X-RED; Stoe & Cie, 1995) | k = −19→19 |
Tmin = 0.734, Tmax = 0.772 | l = −9→14 |
7868 measured reflections | 5 standard reflections every 90 min |
4084 independent reflections | intensity decay: 13.5% |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | All 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 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −1.04 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 | |
Cl11 | 0.65662 (5) | 0.11196 (3) | 0.58423 (5) | 0.03489 (12) | |
Cl12 | 0.11345 (5) | 0.19462 (3) | 0.12896 (5) | 0.03317 (12) | |
S21 | 0.55184 (7) | 0.43488 (4) | 0.65306 (6) | 0.04652 (16) | |
C21 | 0.47881 (18) | 0.36081 (12) | 0.74754 (17) | 0.0275 (3) | |
N31 | 0.39775 (16) | 0.39372 (10) | 0.83449 (15) | 0.0268 (3) | |
C41 | 0.33230 (19) | 0.33689 (13) | 0.91237 (18) | 0.0298 (4) | |
C51 | 0.3497 (2) | 0.23587 (14) | 0.9049 (2) | 0.0353 (4) | |
C61 | 0.4304 (2) | 0.20237 (13) | 0.8208 (2) | 0.0356 (4) | |
N11 | 0.49212 (17) | 0.26343 (11) | 0.74432 (16) | 0.0320 (3) | |
N41 | 0.2569 (2) | 0.37821 (15) | 0.9907 (2) | 0.0462 (5) | |
S22 | −0.07889 (9) | 0.96708 (4) | 0.29048 (9) | 0.0769 (3) | |
C22 | 0.0337 (2) | 0.91902 (13) | 0.2060 (2) | 0.0349 (4) | |
N32 | 0.05179 (16) | 0.82203 (10) | 0.19994 (16) | 0.0300 (3) | |
C42 | 0.13773 (18) | 0.77848 (12) | 0.12707 (17) | 0.0286 (4) | |
C52 | 0.2155 (2) | 0.83810 (14) | 0.0543 (2) | 0.0326 (4) | |
C62 | 0.2000 (2) | 0.93362 (13) | 0.06222 (19) | 0.0331 (4) | |
N12 | 0.11114 (18) | 0.97273 (12) | 0.13647 (17) | 0.0342 (4) | |
N42 | 0.1470 (2) | 0.68471 (12) | 0.1279 (2) | 0.0430 (4) | |
H31 | 0.391 (2) | 0.4542 (17) | 0.844 (2) | 0.027 (5)* | |
H51 | 0.310 (3) | 0.1912 (19) | 0.951 (2) | 0.041 (6)* | |
H61 | 0.451 (3) | 0.1364 (19) | 0.812 (2) | 0.040 (6)* | |
H11 | 0.544 (3) | 0.238 (2) | 0.691 (2) | 0.048 (7)* | |
H411 | 0.254 (3) | 0.442 (2) | 0.991 (3) | 0.061 (8)* | |
H412 | 0.217 (3) | 0.347 (2) | 1.033 (3) | 0.050 (8)* | |
H32 | 0.003 (3) | 0.783 (2) | 0.250 (2) | 0.054 (7)* | |
H52 | 0.279 (3) | 0.8091 (19) | 0.002 (2) | 0.051 (7)* | |
H62 | 0.248 (2) | 0.9771 (16) | 0.020 (2) | 0.029 (5)* | |
H12 | 0.109 (2) | 1.028 (2) | 0.140 (2) | 0.040 (7)* | |
H421 | 0.105 (3) | 0.649 (2) | 0.174 (3) | 0.054 (8)* | |
H422 | 0.202 (3) | 0.659 (2) | 0.077 (3) | 0.053 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl11 | 0.0415 (3) | 0.0261 (2) | 0.0394 (2) | −0.00042 (17) | 0.01385 (19) | 0.00233 (17) |
Cl12 | 0.0389 (2) | 0.02238 (19) | 0.0413 (2) | −0.00043 (16) | 0.01604 (19) | −0.00015 (16) |
S21 | 0.0635 (4) | 0.0291 (2) | 0.0565 (3) | −0.0023 (2) | 0.0401 (3) | 0.0037 (2) |
C21 | 0.0318 (9) | 0.0219 (7) | 0.0310 (8) | 0.0011 (6) | 0.0115 (7) | 0.0008 (6) |
N31 | 0.0326 (8) | 0.0189 (6) | 0.0314 (7) | 0.0002 (6) | 0.0131 (6) | −0.0001 (5) |
C41 | 0.0333 (9) | 0.0268 (8) | 0.0316 (9) | −0.0006 (7) | 0.0124 (7) | 0.0017 (6) |
C51 | 0.0415 (10) | 0.0256 (8) | 0.0418 (10) | −0.0019 (7) | 0.0157 (8) | 0.0070 (7) |
C61 | 0.0459 (11) | 0.0191 (8) | 0.0435 (10) | 0.0026 (7) | 0.0125 (8) | 0.0028 (7) |
N11 | 0.0389 (9) | 0.0218 (7) | 0.0385 (8) | 0.0050 (6) | 0.0162 (7) | −0.0006 (6) |
N41 | 0.0607 (13) | 0.0346 (9) | 0.0521 (11) | 0.0011 (8) | 0.0372 (10) | 0.0006 (8) |
S22 | 0.1063 (6) | 0.0269 (3) | 0.1211 (7) | 0.0099 (3) | 0.0932 (6) | 0.0045 (3) |
C22 | 0.0417 (10) | 0.0227 (8) | 0.0456 (11) | 0.0016 (7) | 0.0231 (9) | 0.0012 (7) |
N32 | 0.0349 (8) | 0.0211 (6) | 0.0381 (8) | 0.0003 (6) | 0.0189 (7) | 0.0019 (6) |
C42 | 0.0309 (9) | 0.0230 (7) | 0.0338 (9) | 0.0012 (6) | 0.0111 (7) | 0.0003 (6) |
C52 | 0.0350 (9) | 0.0284 (8) | 0.0384 (10) | 0.0003 (7) | 0.0185 (8) | 0.0013 (7) |
C62 | 0.0359 (10) | 0.0289 (9) | 0.0378 (10) | −0.0032 (7) | 0.0165 (8) | 0.0039 (7) |
N12 | 0.0426 (9) | 0.0191 (7) | 0.0452 (9) | 0.0009 (6) | 0.0210 (7) | 0.0031 (6) |
N42 | 0.0551 (11) | 0.0219 (7) | 0.0588 (12) | 0.0037 (7) | 0.0312 (10) | 0.0023 (7) |
Geometric parameters (Å, º) top
S21—C21 | 1.6537 (17) | S22—C22 | 1.6567 (19) |
C21—N11 | 1.360 (2) | C22—N12 | 1.351 (2) |
C21—N31 | 1.368 (2) | C22—N32 | 1.361 (2) |
N31—C41 | 1.357 (2) | N32—C42 | 1.360 (2) |
N31—H31 | 0.85 (2) | N32—H32 | 0.93 (3) |
C41—N41 | 1.311 (2) | C42—N42 | 1.305 (2) |
C41—C51 | 1.417 (3) | C42—C52 | 1.420 (2) |
C51—C61 | 1.346 (3) | C52—C62 | 1.339 (3) |
C51—H51 | 0.91 (3) | C52—H52 | 0.97 (3) |
C61—N11 | 1.362 (2) | C62—N12 | 1.364 (2) |
C61—H61 | 0.95 (3) | C62—H62 | 0.91 (2) |
N11—H11 | 0.88 (3) | N12—H12 | 0.77 (3) |
N41—H411 | 0.89 (3) | N42—H421 | 0.84 (3) |
N41—H412 | 0.76 (3) | N42—H422 | 0.89 (3) |
| | | |
N11—C21—N31 | 114.68 (15) | N12—C22—N32 | 115.59 (16) |
N11—C21—S21 | 123.45 (13) | N12—C22—S22 | 122.58 (14) |
N31—C21—S21 | 121.86 (13) | N32—C22—S22 | 121.81 (14) |
C41—N31—C21 | 124.85 (15) | C42—N32—C22 | 124.32 (15) |
C41—N31—H31 | 117.1 (14) | C42—N32—H32 | 117.8 (17) |
C21—N31—H31 | 117.9 (15) | C22—N32—H32 | 117.9 (17) |
N41—C41—N31 | 118.39 (17) | N42—C42—N32 | 119.35 (17) |
N41—C41—C51 | 123.55 (17) | N42—C42—C52 | 122.75 (17) |
N31—C41—C51 | 118.05 (16) | N32—C42—C52 | 117.89 (15) |
C61—C51—C41 | 117.83 (17) | C62—C52—C42 | 117.92 (16) |
C61—C51—H51 | 116.8 (16) | C62—C52—H52 | 122.2 (16) |
C41—C51—H51 | 125.4 (16) | C42—C52—H52 | 119.9 (16) |
C51—C61—N11 | 121.15 (17) | C52—C62—N12 | 121.25 (17) |
C51—C61—H61 | 123.6 (15) | C52—C62—H62 | 123.6 (14) |
N11—C61—H61 | 115.3 (15) | N12—C62—H62 | 115.1 (14) |
C21—N11—C61 | 123.44 (16) | C22—N12—C62 | 123.00 (16) |
C21—N11—H11 | 119.2 (18) | C22—N12—H12 | 120.4 (19) |
C61—N11—H11 | 117.4 (18) | C62—N12—H12 | 116.6 (19) |
C41—N41—H411 | 117 (2) | C42—N42—H421 | 123 (2) |
C41—N41—H412 | 120 (2) | C42—N42—H422 | 116.8 (19) |
H411—N41—H412 | 123 (3) | H421—N42—H422 | 120 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···Cl11 | 0.88 (3) | 2.43 (3) | 3.2567 (18) | 157 (2) |
N12—H12···Cl12i | 0.77 (3) | 2.32 (3) | 3.0822 (18) | 173.5 (19) |
N31—H31···Cl11ii | 0.85 (2) | 2.38 (2) | 3.2100 (16) | 165.5 (19) |
N32—H32···Cl12iii | 0.93 (3) | 2.20 (3) | 3.1270 (17) | 178 (3) |
N41—H411···Cl11ii | 0.89 (3) | 2.68 (3) | 3.474 (2) | 150 (3) |
N41—H412···Cl12iv | 0.77 (3) | 2.61 (3) | 3.340 (2) | 160 (3) |
N42—H421···S22v | 0.84 (3) | 2.57 (3) | 3.2344 (19) | 137 (3) |
N42—H422···Cl11vi | 0.89 (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, y−1/2, −z+1/2; (vi) −x+1, y+1/2, −z+1/2. |
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