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The title compound, C5H9N3S, which exhibits a hypoglycemic effect, crystallizes in space group P21/c. The structure is held together by a network of intermolecular N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802018147/cf6211sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802018147/cf6211Isup2.hkl
Contains datablock I

CCDC reference: 200766

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.066
  • wR factor = 0.191
  • Data-to-parameter ratio = 16.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_352 Alert C Short N-H Bond (0.87A) N(3) - H(2) = 0.73 Ang. PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(3) - C(4) = 1.43 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

2-amino-5-propyl-1,3,4-thiadiazole top
Crystal data top
C5H9N3SF(000) = 304
Mr = 143.22Dx = 1.262 Mg m3
Monoclinic, P21/cMelting point = 203–205 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.181 (4) ÅCell parameters from 1701 reflections
b = 6.766 (2) Åθ = 3.5–24.2°
c = 11.114 (4) ŵ = 0.35 mm1
β = 100.02 (1)°T = 293 K
V = 753.9 (5) Å3Prism, yellow
Z = 40.35 × 0.25 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1108 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 26.4°, θmin = 2.0°
φ and ω scansh = 1212
5894 measured reflectionsk = 88
1534 independent reflectionsl = 1313
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1025P)2 + 0.1974P]
where P = (Fo2 + 2Fc2)/3
1534 reflections(Δ/σ)max = 0.048
91 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.17 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
S10.20369 (10)1.07773 (14)0.39826 (7)0.0861 (4)
N10.0932 (3)1.2818 (4)0.5448 (2)0.0783 (8)
N30.0791 (4)1.4291 (5)0.3551 (3)0.1100 (13)
N20.1437 (3)1.1161 (4)0.6085 (2)0.0792 (8)
C10.1172 (3)1.2844 (5)0.4335 (3)0.0741 (9)
C20.2014 (4)0.9968 (5)0.5457 (3)0.0809 (9)
C30.2598 (5)0.8030 (7)0.5969 (4)0.1087 (13)
H3D0.25940.80130.68410.130*
H4E0.20240.69670.56050.130*
C40.3926 (6)0.7642 (9)0.5775 (6)0.1378 (18)
H5A0.44920.87600.60580.165*
H6B0.39230.74790.49070.165*
C50.4494 (8)0.5767 (8)0.6458 (7)0.180 (3)
H7A0.43230.58040.72800.269*
H8B0.54380.57040.64720.269*
H9C0.40740.46220.60480.269*
H10.02941.53080.38010.080 (9)*
H20.09261.42220.29280.123 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.1090 (8)0.0990 (7)0.0566 (5)0.0203 (5)0.0320 (5)0.0092 (4)
N10.117 (2)0.0772 (16)0.0477 (13)0.0177 (15)0.0341 (13)0.0028 (11)
N30.171 (3)0.119 (3)0.0523 (16)0.056 (2)0.0531 (19)0.0186 (15)
N20.108 (2)0.0813 (18)0.0535 (14)0.0113 (15)0.0284 (14)0.0040 (12)
C10.098 (2)0.085 (2)0.0443 (14)0.0099 (17)0.0257 (14)0.0028 (14)
C20.097 (2)0.083 (2)0.0645 (19)0.0079 (19)0.0195 (17)0.0029 (17)
C30.130 (4)0.100 (3)0.103 (3)0.019 (3)0.041 (3)0.009 (2)
C40.156 (5)0.135 (4)0.128 (4)0.034 (4)0.039 (3)0.022 (3)
C50.199 (7)0.167 (6)0.176 (7)0.089 (5)0.044 (5)0.063 (5)
Geometric parameters (Å, º) top
S1—C21.731 (4)C3—C41.430 (7)
S1—C11.733 (3)C3—H3D0.970
N1—C11.302 (4)C3—H4E0.970
N1—N21.377 (4)C4—C51.539 (7)
N3—C11.323 (4)C4—H5A0.970
N3—H10.925C4—H6B0.970
N3—H20.730C5—H7A0.960
N2—C21.275 (4)C5—H8B0.960
C2—C31.510 (6)C5—H9C0.960
C2—S1—C187.17 (16)C4—C3—H4E108.5
C1—N1—N2112.6 (2)C2—C3—H4E108.5
C1—N3—H1117.8H3D—C3—H4E107.5
C1—N3—H2119.7C3—C4—C5111.2 (5)
H1—N3—H2122.4C3—C4—H5A109.4
C2—N2—N1113.6 (3)C5—C4—H5A109.4
N1—C1—N3123.6 (3)C3—C4—H6B109.4
N1—C1—S1113.0 (2)C5—C4—H6B109.4
N3—C1—S1123.4 (2)H5A—C4—H6B108.0
N2—C2—C3122.1 (3)C4—C5—H7A109.5
N2—C2—S1113.6 (3)C4—C5—H8B109.5
C3—C2—S1124.2 (3)H7A—C5—H8B109.5
C4—C3—C2115.0 (4)C4—C5—H9C109.5
C4—C3—H3D108.5H7A—C5—H9C109.5
C2—C3—H3D108.5H8B—C5—H9C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1···N1i0.922.062.970 (5)170
N3—H2···N2ii0.732.212.944 (4)176
Symmetry codes: (i) x, y+3, z+1; (ii) x, y+5/2, z1/2.
 

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