organic compounds
In the title compound, C5H11N5S2, the molecule adopts a zwitterionic structure. No H atoms are bonded to the dithiocarboxy S atoms nor to the N atom at the 3-position (N3), but the two imino groups in the biguanide moiety are converted to amino groups. The molecule consists of two planar moieties sharing atom N3; the dihedral angle between them is 58.0 (1)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017775/ob6385sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017775/ob6385Isup2.hkl |
CCDC reference: 248838
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (N-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.037
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.6497 Proportion of unique data used 0.7030 Ratio reflections to parameters 9.9150 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.92 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT420_ALERT_2_C D-H Without Acceptor N2 - H7 ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CrystalStructure; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
(I) top
Crystal data top
C5H11N5S2 | F(000) = 432.00 |
Mr = 205.33 | Dx = 1.453 Mg m−3 |
Monoclinic, P21/n | Melting point: 308 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.7107 Å |
a = 7.979 (2) Å | Cell parameters from 25 reflections |
b = 11.888 (3) Å | θ = 15.2–16.3° |
c = 10.618 (2) Å | µ = 0.52 mm−1 |
β = 111.21 (1)° | T = 296 K |
V = 938.9 (4) Å3 | Prism, yellow |
Z = 4 | 0.39 × 0.39 × 0.32 mm |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.001 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→10 |
Tmin = 0.799, Tmax = 0.846 | k = 0→15 |
2419 measured reflections | l = −13→12 |
2158 independent reflections | 3 standard reflections every 150 reflections |
1517 reflections with I > 3σ(I) | intensity decay: 0.1% |
Refinement top
Refinement on F | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.033 | Weighting scheme based on measured s.u.'s w = 1/σ2(Fo) |
wR(F2) = 0.037 | (Δ/σ)max < 0.001 |
S = 1.71 | Δρmax = 0.22 e Å−3 |
1517 reflections | Δρmin = −0.16 e Å−3 |
153 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.97085 (8) | 0.01363 (7) | 0.69174 (6) | 0.0504 (2) | |
S2 | 0.64702 (8) | 0.14598 (6) | 0.67286 (6) | 0.0422 (2) | |
N1 | 0.5024 (3) | 0.1623 (2) | 0.0216 (2) | 0.0360 (5) | |
N2 | 0.3005 (3) | 0.0683 (2) | 0.0930 (3) | 0.0478 (7) | |
N3 | 0.5996 (2) | 0.0934 (2) | 0.2372 (2) | 0.0359 (5) | |
N4 | 0.4529 (3) | 0.1644 (2) | 0.3762 (2) | 0.0454 (7) | |
N5 | 0.7267 (3) | 0.0688 (2) | 0.4623 (2) | 0.0334 (5) | |
C1 | 0.6787 (4) | 0.2129 (4) | 0.0478 (3) | 0.0550 (9) | |
C2 | 0.3728 (4) | 0.1752 (3) | −0.1155 (3) | 0.0488 (9) | |
C3 | 0.4646 (3) | 0.1102 (2) | 0.1178 (2) | 0.0323 (6) | |
C4 | 0.5826 (3) | 0.1096 (2) | 0.3535 (2) | 0.0315 (6) | |
C5 | 0.7758 (3) | 0.0775 (2) | 0.6009 (2) | 0.0330 (6) | |
H1 | 0.770 (4) | 0.177 (3) | 0.125 (3) | 0.10 (1)* | |
H2 | 0.680 (5) | 0.289 (4) | 0.067 (4) | 0.13 (2)* | |
H3 | 0.711 (4) | 0.204 (3) | −0.026 (3) | 0.09 (1)* | |
H4 | 0.402 (5) | 0.233 (3) | −0.160 (4) | 0.11 (1)* | |
H5 | 0.370 (5) | 0.111 (3) | −0.163 (3) | 0.10 (1)* | |
H6 | 0.260 (4) | 0.183 (2) | −0.117 (3) | 0.061 (9)* | |
H7 | 0.223 (4) | 0.077 (2) | 0.021 (3) | 0.054 (9)* | |
H8 | 0.281 (4) | 0.030 (3) | 0.152 (3) | 0.07 (1)* | |
H9 | 0.375 (3) | 0.196 (2) | 0.311 (3) | 0.052 (8)* | |
H10 | 0.466 (4) | 0.175 (3) | 0.463 (3) | 0.064 (9)* | |
H11 | 0.795 (3) | 0.039 (2) | 0.436 (2) | 0.039 (8)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0362 (3) | 0.0750 (6) | 0.0351 (3) | 0.0099 (4) | 0.0071 (3) | 0.0069 (4) |
S2 | 0.0417 (3) | 0.0497 (4) | 0.0384 (3) | −0.0023 (3) | 0.0182 (3) | −0.0072 (3) |
N1 | 0.037 (1) | 0.042 (1) | 0.027 (1) | −0.004 (1) | 0.009 (1) | −0.000 (1) |
N2 | 0.035 (1) | 0.058 (2) | 0.044 (1) | −0.005 (1) | 0.007 (1) | 0.009 (1) |
N3 | 0.030 (1) | 0.046 (1) | 0.031 (1) | 0.006 (1) | 0.011 (1) | 0.004 (1) |
N4 | 0.039 (1) | 0.060 (2) | 0.037 (1) | 0.019 (1) | 0.012 (1) | 0.006 (1) |
N5 | 0.031 (1) | 0.039 (1) | 0.032 (1) | 0.007 (1) | 0.013 (1) | 0.003 (1) |
C1 | 0.052 (2) | 0.073 (3) | 0.040 (2) | −0.023 (2) | 0.016 (1) | −0.001 (2) |
C2 | 0.047 (2) | 0.061 (2) | 0.031 (1) | 0.012 (2) | 0.006 (1) | 0.002 (1) |
C3 | 0.031 (1) | 0.030 (1) | 0.035 (1) | 0.005 (1) | 0.011 (1) | −0.002 (1) |
C4 | 0.028 (1) | 0.031 (1) | 0.035 (1) | −0.001 (1) | 0.011 (1) | 0.004 (1) |
C5 | 0.030 (1) | 0.034 (1) | 0.035 (1) | −0.008 (1) | 0.012 (1) | 0.002 (1) |
Geometric parameters (Å, º) top
S1—C5 | 1.686 (2) | N2—H7 | 0.80 (2) |
S2—C5 | 1.694 (2) | N2—H8 | 0.84 (3) |
N1—C1 | 1.461 (3) | N4—H9 | 0.83 (2) |
N1—C2 | 1.457 (3) | N4—H10 | 0.89 (3) |
N1—C3 | 1.320 (3) | N5—H11 | 0.78 (2) |
N2—C3 | 1.335 (3) | C1—H1 | 0.97 (3) |
N3—C3 | 1.349 (3) | C1—H2 | 0.93 (4) |
N3—C4 | 1.305 (3) | C1—H3 | 0.92 (4) |
N4—C4 | 1.317 (3) | C2—H4 | 0.92 (4) |
N5—C4 | 1.390 (3) | C2—H5 | 0.91 (3) |
N5—C5 | 1.383 (3) | C2—H6 | 0.90 (3) |
S1···N3i | 3.473 (2) | N3···C2iv | 3.481 (4) |
S2···N2ii | 3.478 (3) | N3···C2iii | 3.507 (4) |
S2···N4iii | 3.448 (2) | N4···C5ii | 3.461 (3) |
S1···N5i | 3.509 (2) | N5···C2iii | 3.464 (4) |
S2···C4ii | 3.507 (2) | C1···C2iii | 3.598 (4) |
N1···N2iv | 3.585 (3) | C2···C4v | 3.385 (4) |
C1—N1—C2 | 115.7 (2) | C4—N4—H9 | 118 (2) |
C1—N1—C3 | 121.3 (2) | C4—N4—H10 | 117 (2) |
C2—N1—C3 | 123.0 (2) | H9—N4—H10 | 124 (3) |
C3—N3—C4 | 123.1 (2) | C4—N5—H11 | 110 (2) |
C4—N5—C5 | 133.5 (2) | C5—N5—H11 | 117 (2) |
N1—C3—N2 | 120.3 (2) | N1—C1—H1 | 111 (2) |
N1—C3—N3 | 118.0 (2) | N1—C1—H2 | 112 (3) |
N2—C3—N3 | 121.5 (2) | H1—C1—H2 | 107 (3) |
N3—C4—N4 | 127.1 (2) | N1—C1—H3 | 110 (2) |
N3—C4—N5 | 113.4 (2) | H1—C1—H3 | 108 (3) |
N4—C4—N5 | 119.3 (2) | H2—C1—H3 | 109 (3) |
S1—C5—S2 | 122.9 (1) | N1—C2—H4 | 112 (3) |
S1—C5—N5 | 115.0 (2) | N1—C2—H5 | 109 (2) |
S2—C5—N5 | 122.1 (2) | H4—C2—H5 | 108 (3) |
C3—N2—H7 | 120 (2) | N1—C2—H6 | 112 (2) |
C3—N2—H8 | 120 (2) | H4—C2—H6 | 111 (3) |
H7—N2—H8 | 120 (3) | H5—C2—H6 | 105 (3) |
C1—N1—C3—N2 | 177.5 (4) | C3—N3—C4—N4 | −14.9 (5) |
C1—N1—C3—N3 | −7.6 (6) | C3—N3—C4—N5 | 169.4 (3) |
C2—N1—C3—N2 | −1.4 (6) | C5—N5—C4—N3 | 171.8 (3) |
C2—N1—C3—N3 | 173.6 (4) | C5—N5—C4—N4 | −4.3 (6) |
C4—N3—C3—N1 | 136.7 (3) | C4—N5—C5—S1 | −178.5 (3) |
C4—N3—C3—N2 | −48.4 (5) | C4—N5—C5—S2 | 2.2 (5) |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1, −y, −z; (v) x−1/2, −y+1/2, z−1/2. |