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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017775/ob6385sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017775/ob6385Isup2.hkl
Contains datablock I

CCDC reference: 248838

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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
C5H11N5S2F(000) = 432.00
Mr = 205.33Dx = 1.453 Mg m3
Monoclinic, P21/nMelting point: 308 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.7107 Å
a = 7.979 (2) ÅCell parameters from 25 reflections
b = 11.888 (3) Åθ = 15.2–16.3°
c = 10.618 (2) ŵ = 0.52 mm1
β = 111.21 (1)°T = 296 K
V = 938.9 (4) Å3Prism, yellow
Z = 40.39 × 0.39 × 0.32 mm
Data collection top
Rigaku AFC-5S
diffractometer
Rint = 0.001
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 010
Tmin = 0.799, Tmax = 0.846k = 015
2419 measured reflectionsl = 1312
2158 independent reflections3 standard reflections every 150 reflections
1517 reflections with I > 3σ(I) intensity decay: 0.1%
Refinement top
Refinement on FAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.033Weighting scheme based on measured s.u.'s w = 1/σ2(Fo)
wR(F2) = 0.037(Δ/σ)max < 0.001
S = 1.71Δρmax = 0.22 e Å3
1517 reflectionsΔρmin = 0.16 e Å3
153 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.97085 (8)0.01363 (7)0.69174 (6)0.0504 (2)
S20.64702 (8)0.14598 (6)0.67286 (6)0.0422 (2)
N10.5024 (3)0.1623 (2)0.0216 (2)0.0360 (5)
N20.3005 (3)0.0683 (2)0.0930 (3)0.0478 (7)
N30.5996 (2)0.0934 (2)0.2372 (2)0.0359 (5)
N40.4529 (3)0.1644 (2)0.3762 (2)0.0454 (7)
N50.7267 (3)0.0688 (2)0.4623 (2)0.0334 (5)
C10.6787 (4)0.2129 (4)0.0478 (3)0.0550 (9)
C20.3728 (4)0.1752 (3)0.1155 (3)0.0488 (9)
C30.4646 (3)0.1102 (2)0.1178 (2)0.0323 (6)
C40.5826 (3)0.1096 (2)0.3535 (2)0.0315 (6)
C50.7758 (3)0.0775 (2)0.6009 (2)0.0330 (6)
H10.770 (4)0.177 (3)0.125 (3)0.10 (1)*
H20.680 (5)0.289 (4)0.067 (4)0.13 (2)*
H30.711 (4)0.204 (3)0.026 (3)0.09 (1)*
H40.402 (5)0.233 (3)0.160 (4)0.11 (1)*
H50.370 (5)0.111 (3)0.163 (3)0.10 (1)*
H60.260 (4)0.183 (2)0.117 (3)0.061 (9)*
H70.223 (4)0.077 (2)0.021 (3)0.054 (9)*
H80.281 (4)0.030 (3)0.152 (3)0.07 (1)*
H90.375 (3)0.196 (2)0.311 (3)0.052 (8)*
H100.466 (4)0.175 (3)0.463 (3)0.064 (9)*
H110.795 (3)0.039 (2)0.436 (2)0.039 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0362 (3)0.0750 (6)0.0351 (3)0.0099 (4)0.0071 (3)0.0069 (4)
S20.0417 (3)0.0497 (4)0.0384 (3)0.0023 (3)0.0182 (3)0.0072 (3)
N10.037 (1)0.042 (1)0.027 (1)0.004 (1)0.009 (1)0.000 (1)
N20.035 (1)0.058 (2)0.044 (1)0.005 (1)0.007 (1)0.009 (1)
N30.030 (1)0.046 (1)0.031 (1)0.006 (1)0.011 (1)0.004 (1)
N40.039 (1)0.060 (2)0.037 (1)0.019 (1)0.012 (1)0.006 (1)
N50.031 (1)0.039 (1)0.032 (1)0.007 (1)0.013 (1)0.003 (1)
C10.052 (2)0.073 (3)0.040 (2)0.023 (2)0.016 (1)0.001 (2)
C20.047 (2)0.061 (2)0.031 (1)0.012 (2)0.006 (1)0.002 (1)
C30.031 (1)0.030 (1)0.035 (1)0.005 (1)0.011 (1)0.002 (1)
C40.028 (1)0.031 (1)0.035 (1)0.001 (1)0.011 (1)0.004 (1)
C50.030 (1)0.034 (1)0.035 (1)0.008 (1)0.012 (1)0.002 (1)
Geometric parameters (Å, º) top
S1—C51.686 (2)N2—H70.80 (2)
S2—C51.694 (2)N2—H80.84 (3)
N1—C11.461 (3)N4—H90.83 (2)
N1—C21.457 (3)N4—H100.89 (3)
N1—C31.320 (3)N5—H110.78 (2)
N2—C31.335 (3)C1—H10.97 (3)
N3—C31.349 (3)C1—H20.93 (4)
N3—C41.305 (3)C1—H30.92 (4)
N4—C41.317 (3)C2—H40.92 (4)
N5—C41.390 (3)C2—H50.91 (3)
N5—C51.383 (3)C2—H60.90 (3)
S1···N3i3.473 (2)N3···C2iv3.481 (4)
S2···N2ii3.478 (3)N3···C2iii3.507 (4)
S2···N4iii3.448 (2)N4···C5ii3.461 (3)
S1···N5i3.509 (2)N5···C2iii3.464 (4)
S2···C4ii3.507 (2)C1···C2iii3.598 (4)
N1···N2iv3.585 (3)C2···C4v3.385 (4)
C1—N1—C2115.7 (2)C4—N4—H9118 (2)
C1—N1—C3121.3 (2)C4—N4—H10117 (2)
C2—N1—C3123.0 (2)H9—N4—H10124 (3)
C3—N3—C4123.1 (2)C4—N5—H11110 (2)
C4—N5—C5133.5 (2)C5—N5—H11117 (2)
N1—C3—N2120.3 (2)N1—C1—H1111 (2)
N1—C3—N3118.0 (2)N1—C1—H2112 (3)
N2—C3—N3121.5 (2)H1—C1—H2107 (3)
N3—C4—N4127.1 (2)N1—C1—H3110 (2)
N3—C4—N5113.4 (2)H1—C1—H3108 (3)
N4—C4—N5119.3 (2)H2—C1—H3109 (3)
S1—C5—S2122.9 (1)N1—C2—H4112 (3)
S1—C5—N5115.0 (2)N1—C2—H5109 (2)
S2—C5—N5122.1 (2)H4—C2—H5108 (3)
C3—N2—H7120 (2)N1—C2—H6112 (2)
C3—N2—H8120 (2)H4—C2—H6111 (3)
H7—N2—H8120 (3)H5—C2—H6105 (3)
C1—N1—C3—N2177.5 (4)C3—N3—C4—N414.9 (5)
C1—N1—C3—N37.6 (6)C3—N3—C4—N5169.4 (3)
C2—N1—C3—N21.4 (6)C5—N5—C4—N3171.8 (3)
C2—N1—C3—N3173.6 (4)C5—N5—C4—N44.3 (6)
C4—N3—C3—N1136.7 (3)C4—N5—C5—S1178.5 (3)
C4—N3—C3—N248.4 (5)C4—N5—C5—S22.2 (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) x1/2, y+1/2, z1/2.
 

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