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The molecule of the title compound, C9H9N5S, has a non-planar conformation. In the crystal structure, mol­ecules are connected by N—H...N hydrogen bonds along the b axis. Weak C—H...S inter­actions complete the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040584/kp6075sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040584/kp6075Isup2.hkl
Contains datablock I

CCDC reference: 296600

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Comment top

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.

Experimental top

Yellow crystals of (I) were obtained by slow evaporation of ethanol at room temperature.

Refinement top

All H atoms were found from a difference Fourier map and were refined isotropically.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of (I).
4-Allyl-3-(pyrazin-2-yl)-Δ2-1H-1,2,4-triazole-5(4H)-thione top
Crystal data top
C9H9N5SF(000) = 456
Mr = 219.27Dx = 1.388 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 97 reflections
a = 9.736 (2) Åθ = 6–20.5°
b = 14.750 (2) ŵ = 2.54 mm1
c = 7.913 (2) ÅT = 293 K
β = 112.57 (3)°Prism, yellow
V = 1049.3 (4) Å30.6 × 0.25 × 0.1 mm
Z = 4
Data collection top
Kuma KM-4 four-circle
diffractometer
1213 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 80.3°, θmin = 4.9°
ω–2θ scansh = 011
Absorption correction: for a sphere
Dwiggins (1975) with modifications.
k = 180
Tmin = 0.129, Tmax = 0.236l = 99
2367 measured reflections3 standard reflections every 100 reflections
2242 independent reflections intensity decay: 1.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043All 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 reflectionsΔρmax = 0.31 e Å3
173 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0130 (12)
Crystal data top
C9H9N5SV = 1049.3 (4) Å3
Mr = 219.27Z = 4
Monoclinic, P21/cCu Kα radiation
a = 9.736 (2) ŵ = 2.54 mm1
b = 14.750 (2) ÅT = 293 K
c = 7.913 (2) Å0.6 × 0.25 × 0.1 mm
β = 112.57 (3)°
Data collection top
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 = 0.2363 standard reflections every 100 reflections
2367 measured reflections intensity decay: 1.4%
2242 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.131All H-atom parameters refined
S = 1.03Δρmax = 0.31 e Å3
2242 reflectionsΔρmin = 0.19 e Å3
173 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.26677 (8)0.52957 (4)0.56937 (11)0.0685 (3)
N10.0749 (2)0.40241 (14)0.3669 (3)0.0613 (5)
N20.0529 (2)0.31086 (13)0.3469 (3)0.0606 (5)
N40.26323 (19)0.34319 (11)0.5786 (3)0.0509 (4)
N50.3049 (2)0.14705 (13)0.6434 (3)0.0600 (5)
N60.1086 (2)0.03043 (14)0.3894 (3)0.0620 (5)
C30.1688 (2)0.27623 (15)0.4764 (3)0.0513 (5)
C50.2012 (3)0.42515 (15)0.5044 (4)0.0549 (5)
C60.1897 (2)0.17799 (14)0.5002 (3)0.0505 (5)
C70.0906 (3)0.11939 (16)0.3734 (4)0.0571 (6)
C80.2249 (3)0.00026 (18)0.5318 (4)0.0673 (7)
C90.3211 (3)0.05757 (17)0.6575 (4)0.0661 (7)
C100.4093 (3)0.33613 (16)0.7315 (4)0.0549 (5)
C110.5327 (3)0.32576 (18)0.6678 (4)0.0606 (6)
C120.6335 (4)0.2623 (2)0.7234 (5)0.0797 (8)
H1N0.004 (3)0.4432 (18)0.289 (4)0.068 (8)*
H70.002 (3)0.1444 (19)0.271 (4)0.067 (8)*
H80.241 (3)0.064 (2)0.538 (4)0.071 (8)*
H90.410 (3)0.039 (2)0.746 (4)0.078 (9)*
H1010.426 (3)0.395 (2)0.810 (4)0.079 (9)*
H1020.404 (3)0.2861 (18)0.813 (4)0.058 (7)*
H110.537 (3)0.365 (2)0.582 (5)0.076 (9)*
H1210.710 (4)0.259 (3)0.687 (6)0.121 (14)*
H1220.628 (4)0.221 (3)0.822 (5)0.112 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0724 (4)0.0431 (3)0.0884 (5)0.0047 (3)0.0290 (3)0.0037 (3)
N10.0541 (10)0.0438 (10)0.0756 (14)0.0033 (8)0.0133 (10)0.0064 (10)
N20.0537 (10)0.0452 (10)0.0721 (14)0.0007 (7)0.0120 (9)0.0036 (9)
N40.0510 (9)0.0419 (9)0.0568 (11)0.0009 (7)0.0171 (8)0.0004 (8)
N50.0592 (10)0.0469 (10)0.0635 (13)0.0005 (8)0.0120 (10)0.0048 (9)
N60.0619 (10)0.0478 (10)0.0690 (13)0.0042 (8)0.0171 (9)0.0046 (10)
C30.0522 (11)0.0434 (10)0.0550 (12)0.0008 (8)0.0170 (10)0.0004 (9)
C50.0541 (11)0.0447 (11)0.0667 (15)0.0014 (8)0.0239 (11)0.0044 (10)
C60.0497 (11)0.0424 (10)0.0566 (13)0.0013 (8)0.0172 (10)0.0011 (9)
C70.0542 (12)0.0488 (12)0.0613 (14)0.0020 (9)0.0143 (11)0.0027 (10)
C80.0697 (15)0.0426 (11)0.082 (2)0.0029 (11)0.0200 (14)0.0041 (12)
C90.0643 (13)0.0500 (12)0.0688 (16)0.0023 (11)0.0088 (12)0.0064 (12)
C100.0564 (12)0.0487 (12)0.0526 (13)0.0027 (9)0.0130 (11)0.0014 (10)
C110.0568 (12)0.0596 (13)0.0590 (15)0.0061 (10)0.0152 (11)0.0012 (12)
C120.0687 (17)0.0796 (19)0.089 (2)0.0106 (14)0.0282 (16)0.0030 (17)
Geometric parameters (Å, º) top
S1—C51.671 (2)C6—C71.393 (3)
N1—C51.335 (3)C7—H71.00 (3)
N1—N21.367 (3)C8—C91.371 (4)
N1—H1N0.95 (3)C8—H80.94 (3)
N2—C31.303 (3)C9—H90.92 (3)
N4—C51.378 (3)C10—C111.479 (4)
N4—C31.380 (3)C10—H1011.05 (3)
N4—C101.475 (3)C10—H1021.00 (3)
N5—C91.329 (3)C11—C121.304 (4)
N5—C61.332 (3)C11—H110.91 (3)
N6—C71.323 (3)C12—H1210.89 (4)
N6—C81.333 (3)C12—H1221.01 (4)
C3—C61.465 (3)
C5—N1—N2113.39 (19)C6—C7—H7119.8 (16)
C5—N1—H1N126.0 (17)N6—C8—C9121.6 (2)
N2—N1—H1N120.6 (17)N6—C8—H8116.6 (18)
C3—N2—N1104.26 (18)C9—C8—H8121.7 (18)
C5—N4—C3107.09 (19)N5—C9—C8122.1 (3)
C5—N4—C10122.56 (18)N5—C9—H9114.1 (19)
C3—N4—C10130.23 (18)C8—C9—H9123.0 (19)
C9—N5—C6116.5 (2)N4—C10—C11112.4 (2)
C7—N6—C8117.1 (2)N4—C10—H101107.8 (15)
N2—C3—N4111.2 (2)C11—C10—H101109.1 (15)
N2—C3—C6121.6 (2)N4—C10—H102108.3 (14)
N4—C3—C6127.17 (19)C11—C10—H102113.3 (15)
N1—C5—N4104.1 (2)H101—C10—H102106 (2)
N1—C5—S1127.30 (19)C12—C11—C10124.3 (3)
N4—C5—S1128.65 (19)C12—C11—H11117.9 (19)
N5—C6—C7121.6 (2)C10—C11—H11117.8 (19)
N5—C6—C3118.6 (2)C11—C12—H121123 (3)
C7—C6—C3119.8 (2)C11—C12—H122116 (2)
N6—C7—C6121.1 (2)H121—C12—H122121 (3)
N6—C7—H7119.0 (16)
C5—N1—N2—C30.3 (3)C9—N5—C6—C3178.7 (3)
N1—N2—C3—N40.4 (3)N2—C3—C6—N5175.1 (2)
N1—N2—C3—C6178.8 (2)N4—C3—C6—N55.8 (4)
C5—N4—C3—N20.9 (3)N2—C3—C6—C75.5 (4)
C10—N4—C3—N2176.8 (2)N4—C3—C6—C7173.6 (2)
C5—N4—C3—C6178.3 (2)C8—N6—C7—C60.2 (4)
C10—N4—C3—C62.3 (4)N5—C6—C7—N60.9 (4)
N2—N1—C5—N40.8 (3)C3—C6—C7—N6178.5 (2)
N2—N1—C5—S1179.3 (2)C7—N6—C8—C90.6 (4)
C3—N4—C5—N10.9 (2)C6—N5—C9—C80.0 (5)
C10—N4—C5—N1177.3 (2)N6—C8—C9—N50.7 (5)
C3—N4—C5—S1179.1 (2)C5—N4—C10—C1191.5 (3)
C10—N4—C5—S12.8 (3)C3—N4—C10—C1183.9 (3)
C9—N5—C6—C70.8 (4)N4—C10—C11—C12128.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N6i0.95 (3)1.91 (3)2.844 (3)168 (3)
C9—H9···S1ii0.92 (3)2.92 (3)3.780 (3)156 (3)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC9H9N5S
Mr219.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.736 (2), 14.750 (2), 7.913 (2)
β (°) 112.57 (3)
V3)1049.3 (4)
Z4
Radiation typeCu Kα
µ (mm1)2.54
Crystal size (mm)0.6 × 0.25 × 0.1
Data collection
DiffractometerKuma KM-4 four-circle
diffractometer
Absorption correctionFor a sphere
Dwiggins (1975) with modifications.
Tmin, Tmax0.129, 0.236
No. of measured, independent and
observed [I > 2σ(I)] reflections
2367, 2242, 1213
Rint0.055
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.131, 1.03
No. of reflections2242
No. of parameters173
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)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.

Selected geometric parameters (Å, º) top
S1—C51.671 (2)N4—C31.380 (3)
N1—C51.335 (3)N4—C101.475 (3)
N1—N21.367 (3)C10—C111.479 (4)
N2—C31.303 (3)C11—C121.304 (4)
N4—C51.378 (3)
C10—N4—C3—C62.3 (4)C3—N4—C10—C1183.9 (3)
N4—C3—C6—N55.8 (4)N4—C10—C11—C12128.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N6i0.95 (3)1.91 (3)2.844 (3)168 (3)
C9—H9···S1ii0.92 (3)2.92 (3)3.780 (3)156 (3)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+3/2.
 

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