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access3-Ethyl-4-[(E)-(4-fluorobenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione
aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, Karnataka, India, and cDepartment of Chemistry, St. Philomena's College, Mysore 570 015, Karnataka, India
*Correspondence e-mail: devarajegowda@yahoo.com
In the title compound, C11H11FN4S, the dihedral angle between the 1,2,4-triazole ring and the benzene ring is 25.04 (12)° and an intramoleuclar C—H⋯S interaction leads to an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R22(8) loops.
Related literature
For a related structure and background references, see: Devarajegowda et al. (2010![[Devarajegowda, H. C., Jeyaseelan, S., Sumangala, V., Bojapoojary, & Nayak, S. P. (2010). Acta Cryst. E66, o2512-o2513.]](../../../../../../logos/arrows/e_arr.gif "Devarajegowda, H. C., Jeyaseelan, S., Sumangala, V., Bojapoojary, & Nayak, S. P. (2010). Acta Cryst. E66, o2512-o2513.")
).
![[Scheme 1]](hb6709scheme1.gif)
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536812015346/hb6709sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536812015346/hb6709Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812015346/hb6709Isup3.cml
An equimolar mixture of the triazole (0.02 mol) and 4-fluorobenzaldehyde (0.02 mol) in absolute ethanol (30 ml) was refluxed with concentrated H2SO4 (0.5 ml) for 1–2 hrs. On cooling the reaction mixture, the solid product separated was crystallized from ethanol as colourless blocks. The synthesized compound was evaluated for antibacterial and antifungal activity by cup-plate diffusion method and used as the standard drugs for antibacterial and antifungal activity respectively.
All H atoms were placed at calculated positions and refined as riding, with N—H = 0.86 Å, Csp2—H = 0.93 Å, C(methylene)—H = 0.97 and C(methyl)—H = 0.96 Å. Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and 1.2 for all other H atoms.
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./hb6709fig1thm.gif) | Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./hb6709fig2thm.gif) | Fig. 2. Paciking of the molecules. |
| C11H11FN4S | F(000) = 520 |
| Mr = 250.30 | Dx = 1.343 Mg m−3 |
| Monoclinic, P21/c | Melting point: 414 K |
| Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.7967 (17) Å | Cell parameters from 2182 reflections |
| b = 8.4205 (19) Å | θ = 2.2–25.0° |
| c = 19.138 (4) Å | µ = 0.26 mm−1 |
| β = 99.780 (4)° | T = 293 K |
| V = 1238.2 (5) Å3 | Block, colourless |
| Z = 4 | 0.20 × 0.20 × 0.15 mm |
| Bruker SMART CCD diffractometer | 2182 independent reflections |
| Radiation source: fine-focus sealed tube | 1586 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.050 |
| ω and ϕ scans | θmax = 25.0°, θmin = 2.2° |
| Absorption correction: ψ scan (SADABS; Sheldrick, 2007) | h = −9→9 |
| Tmin = 0.770, Tmax = 1.000 | k = −10→10 |
| 11403 measured reflections | l = −22→22 |
| 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.115 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1712P] where P = (Fo2 + 2Fc2)/3 |
| 2182 reflections | (Δ/σ)max < 0.001 |
| 154 parameters | Δρmax = 0.20 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| C11H11FN4S | V = 1238.2 (5) Å3 |
| Mr = 250.30 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 7.7967 (17) Å | µ = 0.26 mm−1 |
| b = 8.4205 (19) Å | T = 293 K |
| c = 19.138 (4) Å | 0.20 × 0.20 × 0.15 mm |
| β = 99.780 (4)° |
| Bruker SMART CCD diffractometer | 2182 independent reflections |
| Absorption correction: ψ scan (SADABS; Sheldrick, 2007) | 1586 reflections with I > 2σ(I) |
| Tmin = 0.770, Tmax = 1.000 | Rint = 0.050 |
| 11403 measured reflections |
| R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
| wR(F2) = 0.115 | H-atom parameters constrained |
| S = 1.02 | Δρmax = 0.20 e Å−3 |
| 2182 reflections | Δρmin = −0.19 e Å−3 |
| 154 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | 0.22343 (8) | 0.61721 (9) | 0.07429 (3) | 0.0711 (3) | |
| F2 | 1.1525 (2) | 1.1308 (2) | 0.18960 (8) | 0.0886 (5) | |
| N3 | 0.2231 (2) | 0.5813 (2) | −0.12894 (9) | 0.0579 (5) | |
| N4 | 0.1651 (2) | 0.5520 (2) | −0.06628 (9) | 0.0542 (5) | |
| H4 | 0.0729 | 0.4974 | −0.0641 | 0.065* | |
| N5 | 0.3973 (2) | 0.6845 (2) | −0.03736 (9) | 0.0492 (5) | |
| N6 | 0.5370 (2) | 0.7802 (2) | −0.00763 (10) | 0.0536 (5) | |
| C7 | 0.4043 (4) | 0.7150 (5) | −0.23453 (15) | 0.1142 (13) | |
| H7A | 0.4826 | 0.7624 | −0.2622 | 0.171* | |
| H7B | 0.2932 | 0.7669 | −0.2449 | 0.171* | |
| H7C | 0.3906 | 0.6043 | −0.2460 | 0.171* | |
| C8 | 0.4763 (3) | 0.7329 (4) | −0.15769 (12) | 0.0706 (8) | |
| H8A | 0.5896 | 0.6822 | −0.1480 | 0.085* | |
| H8B | 0.4929 | 0.8450 | −0.1469 | 0.085* | |
| C9 | 0.3637 (3) | 0.6635 (3) | −0.11018 (12) | 0.0529 (6) | |
| C10 | 0.2640 (3) | 0.6153 (3) | −0.00883 (11) | 0.0512 (6) | |
| C11 | 0.5946 (3) | 0.7675 (3) | 0.05793 (13) | 0.0555 (6) | |
| H11 | 0.5433 | 0.6957 | 0.0850 | 0.067* | |
| C12 | 0.7417 (3) | 0.8648 (3) | 0.09174 (11) | 0.0499 (6) | |
| C13 | 0.8090 (3) | 0.8408 (3) | 0.16278 (12) | 0.0648 (7) | |
| H13 | 0.7607 | 0.7634 | 0.1881 | 0.078* | |
| C14 | 0.9473 (3) | 0.9307 (3) | 0.19634 (12) | 0.0689 (7) | |
| H14 | 0.9920 | 0.9155 | 0.2441 | 0.083* | |
| C15 | 1.0162 (3) | 1.0415 (3) | 0.15780 (13) | 0.0594 (6) | |
| C16 | 0.9559 (3) | 1.0674 (3) | 0.08733 (12) | 0.0569 (6) | |
| H16 | 1.0078 | 1.1429 | 0.0623 | 0.068* | |
| C17 | 0.8163 (3) | 0.9789 (3) | 0.05422 (12) | 0.0521 (6) | |
| H17 | 0.7723 | 0.9960 | 0.0065 | 0.063* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0555 (4) | 0.1101 (6) | 0.0457 (4) | −0.0195 (4) | 0.0028 (3) | −0.0027 (3) |
| F2 | 0.0719 (10) | 0.1093 (13) | 0.0787 (11) | −0.0335 (9) | −0.0044 (8) | −0.0223 (9) |
| N3 | 0.0501 (11) | 0.0773 (14) | 0.0440 (11) | −0.0060 (10) | 0.0019 (9) | −0.0030 (10) |
| N4 | 0.0456 (10) | 0.0688 (13) | 0.0461 (11) | −0.0116 (9) | 0.0020 (8) | 0.0004 (9) |
| N5 | 0.0397 (10) | 0.0599 (12) | 0.0443 (11) | −0.0034 (9) | −0.0035 (8) | 0.0005 (9) |
| N6 | 0.0432 (10) | 0.0618 (12) | 0.0517 (12) | −0.0058 (9) | −0.0035 (9) | −0.0017 (9) |
| C7 | 0.093 (2) | 0.192 (4) | 0.059 (2) | −0.030 (2) | 0.0190 (17) | 0.000 (2) |
| C8 | 0.0578 (15) | 0.099 (2) | 0.0547 (16) | −0.0130 (14) | 0.0075 (12) | 0.0037 (14) |
| C9 | 0.0456 (13) | 0.0638 (15) | 0.0466 (14) | 0.0002 (11) | −0.0002 (10) | 0.0019 (11) |
| C10 | 0.0416 (12) | 0.0599 (14) | 0.0488 (13) | −0.0004 (11) | −0.0023 (10) | 0.0010 (11) |
| C11 | 0.0431 (12) | 0.0637 (16) | 0.0551 (15) | −0.0021 (11) | −0.0050 (11) | 0.0101 (12) |
| C12 | 0.0409 (11) | 0.0600 (15) | 0.0462 (13) | −0.0001 (11) | −0.0002 (10) | 0.0006 (11) |
| C13 | 0.0508 (14) | 0.0891 (19) | 0.0507 (15) | −0.0103 (13) | −0.0026 (11) | 0.0105 (13) |
| C14 | 0.0545 (14) | 0.103 (2) | 0.0444 (14) | −0.0125 (14) | −0.0050 (11) | 0.0015 (14) |
| C15 | 0.0436 (13) | 0.0717 (17) | 0.0591 (15) | −0.0072 (12) | −0.0017 (11) | −0.0137 (13) |
| C16 | 0.0531 (13) | 0.0570 (15) | 0.0601 (15) | −0.0048 (11) | 0.0082 (11) | −0.0028 (12) |
| C17 | 0.0516 (13) | 0.0573 (14) | 0.0449 (12) | 0.0041 (11) | 0.0007 (10) | −0.0003 (11) |
| S1—C10 | 1.674 (2) | C8—H8A | 0.9700 |
| F2—C15 | 1.358 (3) | C8—H8B | 0.9700 |
| N3—C9 | 1.295 (3) | C11—C12 | 1.467 (3) |
| N3—N4 | 1.374 (2) | C11—H11 | 0.9300 |
| N4—C10 | 1.341 (3) | C12—C17 | 1.385 (3) |
| N4—H4 | 0.8600 | C12—C13 | 1.387 (3) |
| N5—C10 | 1.382 (3) | C13—C14 | 1.383 (3) |
| N5—C9 | 1.385 (3) | C13—H13 | 0.9300 |
| N5—N6 | 1.396 (2) | C14—C15 | 1.355 (3) |
| N6—C11 | 1.263 (3) | C14—H14 | 0.9300 |
| C7—C8 | 1.490 (4) | C15—C16 | 1.368 (3) |
| C7—H7A | 0.9600 | C16—C17 | 1.381 (3) |
| C7—H7B | 0.9600 | C16—H16 | 0.9300 |
| C7—H7C | 0.9600 | C17—H17 | 0.9300 |
| C8—C9 | 1.487 (3) | ||
| C9—N3—N4 | 104.05 (17) | N4—C10—S1 | 127.43 (17) |
| C10—N4—N3 | 114.55 (18) | N5—C10—S1 | 130.33 (17) |
| C10—N4—H4 | 122.7 | N6—C11—C12 | 120.7 (2) |
| N3—N4—H4 | 122.7 | N6—C11—H11 | 119.7 |
| C10—N5—C9 | 108.50 (18) | C12—C11—H11 | 119.7 |
| C10—N5—N6 | 132.02 (18) | C17—C12—C13 | 119.1 (2) |
| C9—N5—N6 | 118.99 (18) | C17—C12—C11 | 121.6 (2) |
| C11—N6—N5 | 118.52 (19) | C13—C12—C11 | 119.2 (2) |
| C8—C7—H7A | 109.5 | C14—C13—C12 | 120.7 (2) |
| C8—C7—H7B | 109.5 | C14—C13—H13 | 119.6 |
| H7A—C7—H7B | 109.5 | C12—C13—H13 | 119.6 |
| C8—C7—H7C | 109.5 | C15—C14—C13 | 118.3 (2) |
| H7A—C7—H7C | 109.5 | C15—C14—H14 | 120.9 |
| H7B—C7—H7C | 109.5 | C13—C14—H14 | 120.9 |
| C9—C8—C7 | 113.6 (2) | C14—C15—F2 | 119.3 (2) |
| C9—C8—H8A | 108.8 | C14—C15—C16 | 123.0 (2) |
| C7—C8—H8A | 108.8 | F2—C15—C16 | 117.7 (2) |
| C9—C8—H8B | 108.8 | C15—C16—C17 | 118.6 (2) |
| C7—C8—H8B | 108.8 | C15—C16—H16 | 120.7 |
| H8A—C8—H8B | 107.7 | C17—C16—H16 | 120.7 |
| N3—C9—N5 | 110.71 (19) | C16—C17—C12 | 120.3 (2) |
| N3—C9—C8 | 126.9 (2) | C16—C17—H17 | 119.9 |
| N5—C9—C8 | 122.3 (2) | C12—C17—H17 | 119.9 |
| N4—C10—N5 | 102.12 (18) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N4—H4···S1i | 0.86 | 2.48 | 3.3275 (19) | 168 |
| C11—H11···S1 | 0.93 | 2.55 | 3.222 (3) | 129 |
| Symmetry code: (i) −x, −y+1, −z. |
Experimental details
| Crystal data | |
| Chemical formula | C11H11FN4S |
| Mr | 250.30 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 293 |
| a, b, c (Å) | 7.7967 (17), 8.4205 (19), 19.138 (4) |
| β (°) | 99.780 (4) |
| V (Å3) | 1238.2 (5) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.26 |
| Crystal size (mm) | 0.20 × 0.20 × 0.15 |
| Data collection | |
| Diffractometer | Bruker SMART CCD diffractometer |
| Absorption correction | ψ scan (SADABS; Sheldrick, 2007) |
| Tmin, Tmax | 0.770, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 11403, 2182, 1586 |
| Rint | 0.050 |
| (sin θ/λ)max (Å−1) | 0.595 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.115, 1.02 |
| No. of reflections | 2182 |
| No. of parameters | 154 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.20, −0.19 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
| D—H···A | D—H | H···A | D···A | D—H···A |
| N4—H4···S1i | 0.86 | 2.48 | 3.3275 (19) | 168 |
| C11—H11···S1 | 0.93 | 2.55 | 3.222 (3) | 129 |
| Symmetry code: (i) −x, −y+1, −z. |
Acknowledgements
The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for the data collection.
References
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Devarajegowda, H. C., Jeyaseelan, S., Sumangala, V., Bojapoojary, & Nayak, S. P. (2010). Acta Cryst. E66, o2512–o2513. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Earlier we reported the crystal structure of 1-{1-[2,8- Bis(trifluoromethyl)-4-quinolyl]-5-methyl-1H-1,2,3-triazol- 4-yl}ethanone (Devarajegowda et al.,2010). We report here the crystal structure of the title compound (Fig. 1). The packing of the molecules in the title structure is depicted in Fig. 2. The 1,2,4 triazole ring (N3 N4 N5 C9 C10 is not coplanar with the benzene ring (C12—C17) system; the dihedral angle between the two planes being 25.04 (12)°. The crystal structure is characterized by intermolecular N4—H4···S1 and intramolecular C11—H11···S1 interactions are observed (Table 1).