Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040584/kp6075sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040584/kp6075Isup2.hkl |
CCDC reference: 296600
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.131
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94
Author Response: On our KM4 four-circle diffractometer max. theta is to 80\% only |
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. S1 .. 2.92 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Yellow crystals of (I) were obtained by slow evaporation of ethanol at room temperature.
All H atoms were found from a difference Fourier map and were refined isotropically.
Data collection: KM-4 Software (Kuma, 1991); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I), with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. The crystal packing of (I). |
C9H9N5S | F(000) = 456 |
Mr = 219.27 | Dx = 1.388 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 97 reflections |
a = 9.736 (2) Å | θ = 6–20.5° |
b = 14.750 (2) Å | µ = 2.54 mm−1 |
c = 7.913 (2) Å | T = 293 K |
β = 112.57 (3)° | Prism, yellow |
V = 1049.3 (4) Å3 | 0.6 × 0.25 × 0.1 mm |
Z = 4 |
Kuma KM-4 four-circle diffractometer | 1213 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.055 |
Graphite monochromator | θmax = 80.3°, θmin = 4.9° |
ω–2θ scans | h = 0→11 |
Absorption correction: for a sphere Dwiggins (1975) with modifications. | k = −18→0 |
Tmin = 0.129, Tmax = 0.236 | l = −9→9 |
2367 measured reflections | 3 standard reflections every 100 reflections |
2242 independent reflections | intensity decay: 1.4% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | All H-atom parameters refined |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0796P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2242 reflections | Δρmax = 0.31 e Å−3 |
173 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0130 (12) |
C9H9N5S | V = 1049.3 (4) Å3 |
Mr = 219.27 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 9.736 (2) Å | µ = 2.54 mm−1 |
b = 14.750 (2) Å | T = 293 K |
c = 7.913 (2) Å | 0.6 × 0.25 × 0.1 mm |
β = 112.57 (3)° |
Kuma KM-4 four-circle diffractometer | 1213 reflections with I > 2σ(I) |
Absorption correction: for a sphere Dwiggins (1975) with modifications. | Rint = 0.055 |
Tmin = 0.129, Tmax = 0.236 | 3 standard reflections every 100 reflections |
2367 measured reflections | intensity decay: 1.4% |
2242 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.131 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.31 e Å−3 |
2242 reflections | Δρmin = −0.19 e Å−3 |
173 parameters |
Experimental. Absorption correction: for a sphere Interpolation using Int·Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of µ R in the range 0–2.5, and Int·Tab. Vol·II (1959). p.302; Table 5.3.6 B for µ R in the range 2.6–10.0. The interpolation procedure of C·W·Dwiggins Jr. (Acta Cryst. (1975). A31,146–148) is used with modifications. |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 8.1629 (0.0073) x − 0.4585 (0.0166) y + 6.5223 (0.0060) z = 1.6379 (0.0040) * −0.0054 (0.0017) C6 * 0.0034 (0.0018) C7 * −0.0046 (0.0021) C8 * 0.0027 (0.0022) C9 * 0.0024 (0.0019) N5 * 0.0016 (0.0018) N6 Rms deviation of fitted atoms = 0.0036 − 7.6426 (0.0084) x + 0.3514 (0.0193) y + 6.9075 (0.0060) z = 2.1006 (0.0076) Angle to previous plane (with approximate e.s.d.) = 6.14 (0.14) * 0.0029 (0.0015) N1 * 0.0004 (0.0015) N2 * −0.0035 (0.0014) C3 * 0.0050 (0.0013) N4 * −0.0048 (0.0014) C5 − 0.0204 (0.0039) S1 Rms deviation of fitted atoms = 0.0037 3.0436 (0.0183) x + 8.7549 (0.0554) y + 4.4694 (0.0288) z = 7.4580 (0.0050) Angle to previous plane (with approximate e.s.d.) = 76.83 (0.18) * 0.0000 (0.0000) C10 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C12 Rms deviation of fitted atoms = 0.0000 |
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 | 0.26677 (8) | 0.52957 (4) | 0.56937 (11) | 0.0685 (3) | |
N1 | 0.0749 (2) | 0.40241 (14) | 0.3669 (3) | 0.0613 (5) | |
N2 | 0.0529 (2) | 0.31086 (13) | 0.3469 (3) | 0.0606 (5) | |
N4 | 0.26323 (19) | 0.34319 (11) | 0.5786 (3) | 0.0509 (4) | |
N5 | 0.3049 (2) | 0.14705 (13) | 0.6434 (3) | 0.0600 (5) | |
N6 | 0.1086 (2) | 0.03043 (14) | 0.3894 (3) | 0.0620 (5) | |
C3 | 0.1688 (2) | 0.27623 (15) | 0.4764 (3) | 0.0513 (5) | |
C5 | 0.2012 (3) | 0.42515 (15) | 0.5044 (4) | 0.0549 (5) | |
C6 | 0.1897 (2) | 0.17799 (14) | 0.5002 (3) | 0.0505 (5) | |
C7 | 0.0906 (3) | 0.11939 (16) | 0.3734 (4) | 0.0571 (6) | |
C8 | 0.2249 (3) | −0.00026 (18) | 0.5318 (4) | 0.0673 (7) | |
C9 | 0.3211 (3) | 0.05757 (17) | 0.6575 (4) | 0.0661 (7) | |
C10 | 0.4093 (3) | 0.33613 (16) | 0.7315 (4) | 0.0549 (5) | |
C11 | 0.5327 (3) | 0.32576 (18) | 0.6678 (4) | 0.0606 (6) | |
C12 | 0.6335 (4) | 0.2623 (2) | 0.7234 (5) | 0.0797 (8) | |
H1N | 0.004 (3) | 0.4432 (18) | 0.289 (4) | 0.068 (8)* | |
H7 | 0.002 (3) | 0.1444 (19) | 0.271 (4) | 0.067 (8)* | |
H8 | 0.241 (3) | −0.064 (2) | 0.538 (4) | 0.071 (8)* | |
H9 | 0.410 (3) | 0.039 (2) | 0.746 (4) | 0.078 (9)* | |
H101 | 0.426 (3) | 0.395 (2) | 0.810 (4) | 0.079 (9)* | |
H102 | 0.404 (3) | 0.2861 (18) | 0.813 (4) | 0.058 (7)* | |
H11 | 0.537 (3) | 0.365 (2) | 0.582 (5) | 0.076 (9)* | |
H121 | 0.710 (4) | 0.259 (3) | 0.687 (6) | 0.121 (14)* | |
H122 | 0.628 (4) | 0.221 (3) | 0.822 (5) | 0.112 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0724 (4) | 0.0431 (3) | 0.0884 (5) | −0.0047 (3) | 0.0290 (3) | −0.0037 (3) |
N1 | 0.0541 (10) | 0.0438 (10) | 0.0756 (14) | 0.0033 (8) | 0.0133 (10) | 0.0064 (10) |
N2 | 0.0537 (10) | 0.0452 (10) | 0.0721 (14) | 0.0007 (7) | 0.0120 (9) | 0.0036 (9) |
N4 | 0.0510 (9) | 0.0419 (9) | 0.0568 (11) | −0.0009 (7) | 0.0171 (8) | −0.0004 (8) |
N5 | 0.0592 (10) | 0.0469 (10) | 0.0635 (13) | 0.0005 (8) | 0.0120 (10) | 0.0048 (9) |
N6 | 0.0619 (10) | 0.0478 (10) | 0.0690 (13) | −0.0042 (8) | 0.0171 (9) | −0.0046 (10) |
C3 | 0.0522 (11) | 0.0434 (10) | 0.0550 (12) | −0.0008 (8) | 0.0170 (10) | 0.0004 (9) |
C5 | 0.0541 (11) | 0.0447 (11) | 0.0667 (15) | 0.0014 (8) | 0.0239 (11) | 0.0044 (10) |
C6 | 0.0497 (11) | 0.0424 (10) | 0.0566 (13) | −0.0013 (8) | 0.0172 (10) | 0.0011 (9) |
C7 | 0.0542 (12) | 0.0488 (12) | 0.0613 (14) | −0.0020 (9) | 0.0143 (11) | −0.0027 (10) |
C8 | 0.0697 (15) | 0.0426 (11) | 0.082 (2) | 0.0029 (11) | 0.0200 (14) | 0.0041 (12) |
C9 | 0.0643 (13) | 0.0500 (12) | 0.0688 (16) | 0.0023 (11) | 0.0088 (12) | 0.0064 (12) |
C10 | 0.0564 (12) | 0.0487 (12) | 0.0526 (13) | −0.0027 (9) | 0.0130 (11) | −0.0014 (10) |
C11 | 0.0568 (12) | 0.0596 (13) | 0.0590 (15) | −0.0061 (10) | 0.0152 (11) | 0.0012 (12) |
C12 | 0.0687 (17) | 0.0796 (19) | 0.089 (2) | 0.0106 (14) | 0.0282 (16) | 0.0030 (17) |
S1—C5 | 1.671 (2) | C6—C7 | 1.393 (3) |
N1—C5 | 1.335 (3) | C7—H7 | 1.00 (3) |
N1—N2 | 1.367 (3) | C8—C9 | 1.371 (4) |
N1—H1N | 0.95 (3) | C8—H8 | 0.94 (3) |
N2—C3 | 1.303 (3) | C9—H9 | 0.92 (3) |
N4—C5 | 1.378 (3) | C10—C11 | 1.479 (4) |
N4—C3 | 1.380 (3) | C10—H101 | 1.05 (3) |
N4—C10 | 1.475 (3) | C10—H102 | 1.00 (3) |
N5—C9 | 1.329 (3) | C11—C12 | 1.304 (4) |
N5—C6 | 1.332 (3) | C11—H11 | 0.91 (3) |
N6—C7 | 1.323 (3) | C12—H121 | 0.89 (4) |
N6—C8 | 1.333 (3) | C12—H122 | 1.01 (4) |
C3—C6 | 1.465 (3) | ||
C5—N1—N2 | 113.39 (19) | C6—C7—H7 | 119.8 (16) |
C5—N1—H1N | 126.0 (17) | N6—C8—C9 | 121.6 (2) |
N2—N1—H1N | 120.6 (17) | N6—C8—H8 | 116.6 (18) |
C3—N2—N1 | 104.26 (18) | C9—C8—H8 | 121.7 (18) |
C5—N4—C3 | 107.09 (19) | N5—C9—C8 | 122.1 (3) |
C5—N4—C10 | 122.56 (18) | N5—C9—H9 | 114.1 (19) |
C3—N4—C10 | 130.23 (18) | C8—C9—H9 | 123.0 (19) |
C9—N5—C6 | 116.5 (2) | N4—C10—C11 | 112.4 (2) |
C7—N6—C8 | 117.1 (2) | N4—C10—H101 | 107.8 (15) |
N2—C3—N4 | 111.2 (2) | C11—C10—H101 | 109.1 (15) |
N2—C3—C6 | 121.6 (2) | N4—C10—H102 | 108.3 (14) |
N4—C3—C6 | 127.17 (19) | C11—C10—H102 | 113.3 (15) |
N1—C5—N4 | 104.1 (2) | H101—C10—H102 | 106 (2) |
N1—C5—S1 | 127.30 (19) | C12—C11—C10 | 124.3 (3) |
N4—C5—S1 | 128.65 (19) | C12—C11—H11 | 117.9 (19) |
N5—C6—C7 | 121.6 (2) | C10—C11—H11 | 117.8 (19) |
N5—C6—C3 | 118.6 (2) | C11—C12—H121 | 123 (3) |
C7—C6—C3 | 119.8 (2) | C11—C12—H122 | 116 (2) |
N6—C7—C6 | 121.1 (2) | H121—C12—H122 | 121 (3) |
N6—C7—H7 | 119.0 (16) | ||
C5—N1—N2—C3 | 0.3 (3) | C9—N5—C6—C3 | −178.7 (3) |
N1—N2—C3—N4 | 0.4 (3) | N2—C3—C6—N5 | −175.1 (2) |
N1—N2—C3—C6 | −178.8 (2) | N4—C3—C6—N5 | 5.8 (4) |
C5—N4—C3—N2 | −0.9 (3) | N2—C3—C6—C7 | 5.5 (4) |
C10—N4—C3—N2 | −176.8 (2) | N4—C3—C6—C7 | −173.6 (2) |
C5—N4—C3—C6 | 178.3 (2) | C8—N6—C7—C6 | 0.2 (4) |
C10—N4—C3—C6 | 2.3 (4) | N5—C6—C7—N6 | −0.9 (4) |
N2—N1—C5—N4 | −0.8 (3) | C3—C6—C7—N6 | 178.5 (2) |
N2—N1—C5—S1 | 179.3 (2) | C7—N6—C8—C9 | 0.6 (4) |
C3—N4—C5—N1 | 0.9 (2) | C6—N5—C9—C8 | 0.0 (5) |
C10—N4—C5—N1 | 177.3 (2) | N6—C8—C9—N5 | −0.7 (5) |
C3—N4—C5—S1 | −179.1 (2) | C5—N4—C10—C11 | −91.5 (3) |
C10—N4—C5—S1 | −2.8 (3) | C3—N4—C10—C11 | 83.9 (3) |
C9—N5—C6—C7 | 0.8 (4) | N4—C10—C11—C12 | −128.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N6i | 0.95 (3) | 1.91 (3) | 2.844 (3) | 168 (3) |
C9—H9···S1ii | 0.92 (3) | 2.92 (3) | 3.780 (3) | 156 (3) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C9H9N5S |
Mr | 219.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.736 (2), 14.750 (2), 7.913 (2) |
β (°) | 112.57 (3) |
V (Å3) | 1049.3 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.54 |
Crystal size (mm) | 0.6 × 0.25 × 0.1 |
Data collection | |
Diffractometer | Kuma KM-4 four-circle diffractometer |
Absorption correction | For a sphere Dwiggins (1975) with modifications. |
Tmin, Tmax | 0.129, 0.236 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2367, 2242, 1213 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.131, 1.03 |
No. of reflections | 2242 |
No. of parameters | 173 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.31, −0.19 |
Computer programs: KM-4 Software (Kuma, 1991), KM-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), SHELXL97.
S1—C5 | 1.671 (2) | N4—C3 | 1.380 (3) |
N1—C5 | 1.335 (3) | N4—C10 | 1.475 (3) |
N1—N2 | 1.367 (3) | C10—C11 | 1.479 (4) |
N2—C3 | 1.303 (3) | C11—C12 | 1.304 (4) |
N4—C5 | 1.378 (3) | ||
C10—N4—C3—C6 | 2.3 (4) | C3—N4—C10—C11 | 83.9 (3) |
N4—C3—C6—N5 | 5.8 (4) | N4—C10—C11—C12 | −128.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N6i | 0.95 (3) | 1.91 (3) | 2.844 (3) | 168 (3) |
C9—H9···S1ii | 0.92 (3) | 2.92 (3) | 3.780 (3) | 156 (3) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+3/2. |
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Organic compounds containing aromatic heterocyclic rings have received considerable attention among medicinal chemists because many of them play a role in various biochemical processes. 1,2,4-Triazole and pyrazine derivatives belong to an aromatic heterocyclic group exhibiting a wide range of biological activities, such as antifungal (Demirayak et al., 2000; Doležal et al., 2000; Doležal et al., 2003), antibacterial (Pandeya et al., 2000), anticancer (Invidiata et al., 1991), antiviral (Todoulou et al., 1994), anti-inflammatory (Sahin et al., 2001), antituberculous (Doležal et al., 1996). Chemical modifications leading to the combination of two or more heterocyclic and non-heterocyclic systems produce compounds of significantly enhanced biological profile compare to the parent nuclei. Thus, we have combined the 1,2,4-triazole moiety with the pyrazin-2-yl nucleus, since both of these systems possess well documented biological activities. We present here the crystal structure of 4-allyl-3-(pyrazin-2-yl)-Δ2-1,2,4-triazoline-5-thione, (I) (Fig. 1). The triazole plane forms dihedral angles of 76.8 (2)° and 6.1 (1)° with the propene and pyrazine planes, respectively. In the crystal structure, molecules are linked by intermolecular N—H···N (triazole···pyrazine) hydrogen bonds and C—H···S (pyrazine···triazole) weak interactions (Fig. 2, Table 2) along the [010] direction.