The title compound, C
5H
9N
3S, which exhibits a hypoglycemic effect, crystallizes in space group P2
1/
c. The structure is held together by a network of intermolecular N—H
N hydrogen bonds.
Supporting information
CCDC reference: 200766
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
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
C5H9N3S | F(000) = 304 |
Mr = 143.22 | Dx = 1.262 Mg m−3 |
Monoclinic, P21/c | Melting point = 203–205 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.181 (4) Å | Cell parameters from 1701 reflections |
b = 6.766 (2) Å | θ = 3.5–24.2° |
c = 11.114 (4) Å | µ = 0.35 mm−1 |
β = 100.02 (1)° | T = 293 K |
V = 753.9 (5) Å3 | Prism, yellow |
Z = 4 | 0.35 × 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 tube | Rint = 0.031 |
Graphite monochromator | θmax = 26.4°, θmin = 2.0° |
φ and ω scans | h = −12→12 |
5894 measured reflections | k = −8→8 |
1534 independent reflections | l = −13→13 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.191 | H-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 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.17 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 | |
S1 | 0.20369 (10) | 1.07773 (14) | 0.39826 (7) | 0.0861 (4) | |
N1 | 0.0932 (3) | 1.2818 (4) | 0.5448 (2) | 0.0783 (8) | |
N3 | 0.0791 (4) | 1.4291 (5) | 0.3551 (3) | 0.1100 (13) | |
N2 | 0.1437 (3) | 1.1161 (4) | 0.6085 (2) | 0.0792 (8) | |
C1 | 0.1172 (3) | 1.2844 (5) | 0.4335 (3) | 0.0741 (9) | |
C2 | 0.2014 (4) | 0.9968 (5) | 0.5457 (3) | 0.0809 (9) | |
C3 | 0.2598 (5) | 0.8030 (7) | 0.5969 (4) | 0.1087 (13) | |
H3D | 0.2594 | 0.8013 | 0.6841 | 0.130* | |
H4E | 0.2024 | 0.6967 | 0.5605 | 0.130* | |
C4 | 0.3926 (6) | 0.7642 (9) | 0.5775 (6) | 0.1378 (18) | |
H5A | 0.4492 | 0.8760 | 0.6058 | 0.165* | |
H6B | 0.3923 | 0.7479 | 0.4907 | 0.165* | |
C5 | 0.4494 (8) | 0.5767 (8) | 0.6458 (7) | 0.180 (3) | |
H7A | 0.4323 | 0.5804 | 0.7280 | 0.269* | |
H8B | 0.5438 | 0.5704 | 0.6472 | 0.269* | |
H9C | 0.4074 | 0.4622 | 0.6048 | 0.269* | |
H1 | 0.0294 | 1.5308 | 0.3801 | 0.080 (9)* | |
H2 | 0.0926 | 1.4222 | 0.2928 | 0.123 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.1090 (8) | 0.0990 (7) | 0.0566 (5) | 0.0203 (5) | 0.0320 (5) | −0.0092 (4) |
N1 | 0.117 (2) | 0.0772 (16) | 0.0477 (13) | 0.0177 (15) | 0.0341 (13) | 0.0028 (11) |
N3 | 0.171 (3) | 0.119 (3) | 0.0523 (16) | 0.056 (2) | 0.0531 (19) | 0.0186 (15) |
N2 | 0.108 (2) | 0.0813 (18) | 0.0535 (14) | 0.0113 (15) | 0.0284 (14) | 0.0040 (12) |
C1 | 0.098 (2) | 0.085 (2) | 0.0443 (14) | 0.0099 (17) | 0.0257 (14) | −0.0028 (14) |
C2 | 0.097 (2) | 0.083 (2) | 0.0645 (19) | 0.0079 (19) | 0.0195 (17) | 0.0029 (17) |
C3 | 0.130 (4) | 0.100 (3) | 0.103 (3) | 0.019 (3) | 0.041 (3) | 0.009 (2) |
C4 | 0.156 (5) | 0.135 (4) | 0.128 (4) | 0.034 (4) | 0.039 (3) | 0.022 (3) |
C5 | 0.199 (7) | 0.167 (6) | 0.176 (7) | 0.089 (5) | 0.044 (5) | 0.063 (5) |
Geometric parameters (Å, º) top
S1—C2 | 1.731 (4) | C3—C4 | 1.430 (7) |
S1—C1 | 1.733 (3) | C3—H3D | 0.970 |
N1—C1 | 1.302 (4) | C3—H4E | 0.970 |
N1—N2 | 1.377 (4) | C4—C5 | 1.539 (7) |
N3—C1 | 1.323 (4) | C4—H5A | 0.970 |
N3—H1 | 0.925 | C4—H6B | 0.970 |
N3—H2 | 0.730 | C5—H7A | 0.960 |
N2—C2 | 1.275 (4) | C5—H8B | 0.960 |
C2—C3 | 1.510 (6) | C5—H9C | 0.960 |
| | | |
C2—S1—C1 | 87.17 (16) | C4—C3—H4E | 108.5 |
C1—N1—N2 | 112.6 (2) | C2—C3—H4E | 108.5 |
C1—N3—H1 | 117.8 | H3D—C3—H4E | 107.5 |
C1—N3—H2 | 119.7 | C3—C4—C5 | 111.2 (5) |
H1—N3—H2 | 122.4 | C3—C4—H5A | 109.4 |
C2—N2—N1 | 113.6 (3) | C5—C4—H5A | 109.4 |
N1—C1—N3 | 123.6 (3) | C3—C4—H6B | 109.4 |
N1—C1—S1 | 113.0 (2) | C5—C4—H6B | 109.4 |
N3—C1—S1 | 123.4 (2) | H5A—C4—H6B | 108.0 |
N2—C2—C3 | 122.1 (3) | C4—C5—H7A | 109.5 |
N2—C2—S1 | 113.6 (3) | C4—C5—H8B | 109.5 |
C3—C2—S1 | 124.2 (3) | H7A—C5—H8B | 109.5 |
C4—C3—C2 | 115.0 (4) | C4—C5—H9C | 109.5 |
C4—C3—H3D | 108.5 | H7A—C5—H9C | 109.5 |
C2—C3—H3D | 108.5 | H8B—C5—H9C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H1···N1i | 0.92 | 2.06 | 2.970 (5) | 170 |
N3—H2···N2ii | 0.73 | 2.21 | 2.944 (4) | 176 |
Symmetry codes: (i) −x, −y+3, −z+1; (ii) x, −y+5/2, z−1/2. |