Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051185/bt2545sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051185/bt2545Isup2.hkl |
CCDC reference: 667401
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C)= 0.003 Å
- R factor = 0.034
- wR factor = 0.087
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For potential applications, see: Bohn & Karow (1981); Potts (1961); Santus (1980). For general synthesis procedures, see: Bany & Dobosz (1972); Veverka & Marchalin (1987).
For related literature, see: Bernstein et al. (1995); Desiraju & Steiner (1999).
The title compound was synthesized according to method of Veverka and Marchalin (1987). Crystals were obtained by crystallization from mixture of water, methanol, ethanol and 2-butanone (3:1:5:1).
The hydrogen atoms were placed in calculated positions after four cycles of anisotrophic refinement and were refined as riding on the parent atom with Uiso(H) = 1.2Ueq(C-non-methyl or N) and Uiso(H) = 1.5Ueq(C-methyl or O). The methyl and hydroxyl group was allowed to rotate about its local threefold axis (AFIX 137 and 147 respectively).
The title compound, (I), is a member of 1,2,4-triazoline-3-thione derivatives family, known to posses antibacterial, anitimycotical and antivirostatical activity (Veverka and Marchalin, 1987; Bohn and Karow, 1981; Potts, 1961; Santus, 1980).
All interatomic distances in (I) are normal. The 1,2,4-triazoline ring of (I) can be considered as planar in the range of experimental error. The most deviating N1 atom derives 0.0046 (13) Å from weighted least squares plane of the ring. The C3, C5, S1 atoms deviate respectively 0.082 (3), -0.004 (4), -0.049 (3) Å from this plane. The acetic acid moiety is planar (Table 1) and the most deviating atom is C4 [0.0005 (17) Å] from the weighted O1/O2/C3/C4 least-squares plane. The N3 atom deviates 0.106 (4) Å from this plane. The above mentioned weighted least-squares planes are inclined at 78.61 (7)°.
The molecules of (I) are connected via O1—H1O···N2 hydrogen bonds (Table 1, C11(7) motif (Bernstein et al., 1995)) to zigzag chains extended along the [101] axis. The N1—H1N···S1 hydrogen bonds (Table 1, R22(8) motif) expands the chains to a folded three dimensional sheet in the (-101) plane. In (I) can be found also one C—H···O short contact (Table 1), which, according to Desiraju and Steiner (1999), can be classified as weak hydrogen bond (C11(4) motif).
For potential applications, see: Bohn & Karow (1981); Potts (1961); Santus (1980). For general synthesis procedures, see: Bany & Dobosz (1972); Veverka & Marchalin (1987).
For related literature, see: Bernstein et al. (1995); Desiraju & Steiner (1999).
Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software (Kuma, 1993); data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 for Windows (Version 1.062; Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
C5H7N3O2S | F(000) = 360 |
Mr = 173.20 | Dx = 1.517 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 99 reflections |
a = 5.1706 (3) Å | θ = 2–20° |
b = 9.4818 (6) Å | µ = 0.38 mm−1 |
c = 15.6763 (9) Å | T = 291 K |
β = 99.250 (5)° | Needle, colourless |
V = 758.56 (8) Å3 | 0.22 × 0.07 × 0.07 mm |
Z = 4 |
Kuma KM-4 diffractometer | 1108 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.1°, θmin = 3.4° |
ω–2θ scans | h = −6→6 |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | k = 0→11 |
Tmin = 0.918, Tmax = 0.983 | l = 0→18 |
1354 measured reflections | 3 standard reflections every 100 reflections |
1354 independent reflections | intensity decay: 2.1% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0468P)2] where P = (Fo2 + 2Fc2)/3 |
1354 reflections | (Δ/σ)max < 0.001 |
102 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C5H7N3O2S | V = 758.56 (8) Å3 |
Mr = 173.20 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.1706 (3) Å | µ = 0.38 mm−1 |
b = 9.4818 (6) Å | T = 291 K |
c = 15.6763 (9) Å | 0.22 × 0.07 × 0.07 mm |
β = 99.250 (5)° |
Kuma KM-4 diffractometer | 1108 reflections with I > 2σ(I) |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | Rint = 0.000 |
Tmin = 0.918, Tmax = 0.983 | 3 standard reflections every 100 reflections |
1354 measured reflections | intensity decay: 2.1% |
1354 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.16 e Å−3 |
1354 reflections | Δρmin = −0.24 e Å−3 |
102 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.99527 (11) | 1.04539 (6) | 0.63708 (3) | 0.0393 (2) | |
O1 | 0.7717 (3) | 0.88549 (17) | 0.88096 (9) | 0.0437 (4) | |
H1O | 0.8832 | 0.8517 | 0.9185 | 0.066* | |
C4 | 0.8051 (4) | 0.8362 (2) | 0.80424 (12) | 0.0301 (5) | |
O2 | 0.9822 (3) | 0.76167 (17) | 0.79093 (9) | 0.0420 (4) | |
N1 | 0.7338 (3) | 0.8532 (2) | 0.52587 (10) | 0.0401 (5) | |
H1N | 0.8106 | 0.8759 | 0.4831 | 0.048* | |
N3 | 0.6155 (3) | 0.84909 (19) | 0.64966 (10) | 0.0313 (4) | |
C3 | 0.5851 (4) | 0.8886 (2) | 0.73708 (12) | 0.0336 (5) | |
H3A | 0.4208 | 0.8508 | 0.7495 | 0.040* | |
H3B | 0.5763 | 0.9905 | 0.7407 | 0.040* | |
C2 | 0.7812 (4) | 0.9166 (2) | 0.60293 (12) | 0.0335 (5) | |
N2 | 0.5497 (4) | 0.7480 (2) | 0.52213 (11) | 0.0413 (5) | |
C1 | 0.4797 (4) | 0.7476 (2) | 0.59811 (12) | 0.0347 (5) | |
C5 | 0.2828 (4) | 0.6513 (3) | 0.62525 (15) | 0.0438 (6) | |
H5A | 0.2063 | 0.5947 | 0.5769 | 0.066* | |
H5B | 0.1484 | 0.7056 | 0.6456 | 0.066* | |
H5C | 0.3661 | 0.5911 | 0.6708 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0452 (3) | 0.0464 (4) | 0.0274 (3) | −0.0021 (3) | 0.0090 (2) | −0.0016 (2) |
O1 | 0.0578 (10) | 0.0515 (10) | 0.0206 (8) | 0.0089 (8) | 0.0029 (7) | −0.0014 (7) |
C4 | 0.0347 (11) | 0.0345 (11) | 0.0222 (10) | −0.0032 (9) | 0.0082 (8) | 0.0018 (9) |
O2 | 0.0366 (8) | 0.0546 (10) | 0.0356 (8) | 0.0104 (8) | 0.0087 (7) | 0.0068 (7) |
N1 | 0.0495 (11) | 0.0521 (12) | 0.0202 (9) | −0.0065 (10) | 0.0095 (8) | 0.0007 (8) |
N3 | 0.0322 (9) | 0.0425 (10) | 0.0198 (8) | 0.0043 (8) | 0.0065 (7) | 0.0005 (8) |
C3 | 0.0347 (11) | 0.0459 (13) | 0.0212 (10) | 0.0065 (10) | 0.0073 (8) | −0.0003 (9) |
C2 | 0.0339 (11) | 0.0451 (13) | 0.0216 (10) | 0.0079 (10) | 0.0049 (8) | 0.0022 (9) |
N2 | 0.0481 (11) | 0.0523 (12) | 0.0231 (9) | −0.0059 (10) | 0.0042 (8) | −0.0024 (8) |
C1 | 0.0366 (11) | 0.0445 (13) | 0.0220 (10) | 0.0046 (10) | 0.0015 (8) | 0.0012 (9) |
C5 | 0.0442 (13) | 0.0501 (14) | 0.0375 (13) | −0.0011 (11) | 0.0077 (10) | 0.0021 (11) |
S1—C2 | 1.677 (2) | N3—C1 | 1.374 (3) |
O1—C4 | 1.327 (2) | N3—C3 | 1.453 (2) |
O1—H1O | 0.8200 | C3—H3A | 0.9700 |
C4—O2 | 1.201 (2) | C3—H3B | 0.9700 |
C4—C3 | 1.505 (3) | N2—C1 | 1.299 (3) |
N1—C2 | 1.336 (3) | C1—C5 | 1.480 (3) |
N1—N2 | 1.374 (3) | C5—H5A | 0.9600 |
N1—H1N | 0.8600 | C5—H5B | 0.9600 |
N3—C2 | 1.372 (3) | C5—H5C | 0.9600 |
C4—O1—H1O | 109.5 | H3A—C3—H3B | 107.8 |
O2—C4—O1 | 125.34 (19) | N1—C2—N3 | 103.51 (18) |
O2—C4—C3 | 125.76 (18) | N1—C2—S1 | 129.18 (17) |
O1—C4—C3 | 108.89 (17) | N3—C2—S1 | 127.30 (15) |
C2—N1—N2 | 112.98 (17) | C1—N2—N1 | 104.81 (17) |
C2—N1—H1N | 123.5 | N2—C1—N3 | 110.26 (19) |
N2—N1—H1N | 123.5 | N2—C1—C5 | 124.8 (2) |
C2—N3—C1 | 108.44 (16) | N3—C1—C5 | 124.95 (18) |
C2—N3—C3 | 123.71 (18) | C1—C5—H5A | 109.5 |
C1—N3—C3 | 127.75 (17) | C1—C5—H5B | 109.5 |
N3—C3—C4 | 112.98 (16) | H5A—C5—H5B | 109.5 |
N3—C3—H3A | 109.0 | C1—C5—H5C | 109.5 |
C4—C3—H3A | 109.0 | H5A—C5—H5C | 109.5 |
N3—C3—H3B | 109.0 | H5B—C5—H5C | 109.5 |
C4—C3—H3B | 109.0 | ||
N3—C3—C4—O1 | 175.46 (17) | N3—C3—C4—O2 | −4.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N2i | 0.82 | 1.96 | 2.746 (2) | 162 |
N1—H1N···S1ii | 0.86 | 2.39 | 3.2499 (18) | 176 |
C3—H3A···O2iii | 0.97 | 2.60 | 3.567 (2) | 176 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+2, −y+2, −z+1; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C5H7N3O2S |
Mr | 173.20 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 291 |
a, b, c (Å) | 5.1706 (3), 9.4818 (6), 15.6763 (9) |
β (°) | 99.250 (5) |
V (Å3) | 758.56 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.22 × 0.07 × 0.07 |
Data collection | |
Diffractometer | Kuma KM-4 |
Absorption correction | Numerical (X-RED; Stoe & Cie, 1999) |
Tmin, Tmax | 0.918, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1354, 1354, 1108 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.087, 1.09 |
No. of reflections | 1354 |
No. of parameters | 102 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.24 |
Computer programs: KM-4 Software (Kuma, 1993), DATAPROC (Gałdecki et al., 1998), SHELXS97 (Sheldrick, 1990a), XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 for Windows (Version 1.062; Farrugia, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N2i | 0.82 | 1.96 | 2.746 (2) | 161.8 |
N1—H1N···S1ii | 0.86 | 2.39 | 3.2499 (18) | 175.8 |
C3—H3A···O2iii | 0.97 | 2.60 | 3.567 (2) | 176.2 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+2, −y+2, −z+1; (iii) x−1, y, z. |
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The title compound, (I), is a member of 1,2,4-triazoline-3-thione derivatives family, known to posses antibacterial, anitimycotical and antivirostatical activity (Veverka and Marchalin, 1987; Bohn and Karow, 1981; Potts, 1961; Santus, 1980).
All interatomic distances in (I) are normal. The 1,2,4-triazoline ring of (I) can be considered as planar in the range of experimental error. The most deviating N1 atom derives 0.0046 (13) Å from weighted least squares plane of the ring. The C3, C5, S1 atoms deviate respectively 0.082 (3), -0.004 (4), -0.049 (3) Å from this plane. The acetic acid moiety is planar (Table 1) and the most deviating atom is C4 [0.0005 (17) Å] from the weighted O1/O2/C3/C4 least-squares plane. The N3 atom deviates 0.106 (4) Å from this plane. The above mentioned weighted least-squares planes are inclined at 78.61 (7)°.
The molecules of (I) are connected via O1—H1O···N2 hydrogen bonds (Table 1, C11(7) motif (Bernstein et al., 1995)) to zigzag chains extended along the [101] axis. The N1—H1N···S1 hydrogen bonds (Table 1, R22(8) motif) expands the chains to a folded three dimensional sheet in the (-101) plane. In (I) can be found also one C—H···O short contact (Table 1), which, according to Desiraju and Steiner (1999), can be classified as weak hydrogen bond (C11(4) motif).