Acta Cryst. (2009). E65, o52 [ doi:10.1107/S1600536808040907 ]
The title compound, C11H14N2S, was prepared by the reaction of 1-isothiocyanatobenzene and pyrrolidine. In the crystal structure, intermolecular N-H
S interactions are present.
A mixture of the 1-isothiocyanatobenzene (0.1 mol), and pyrrolidine (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.080 mol, yield 80%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.
H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93 and 0.97 Å and N—H = 0.86 Å, and with Uiso=1.2Ueq(C,N).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).
![[Figure 1]](./at2689fig1thm.gif)
| Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
| C11H14N2S | F(000) = 440 |
| Mr = 206.30 | Dx = 1.316 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 11.195 (2) Å | θ = 1.8–27.0° |
| b = 8.5694 (17) Å | µ = 0.27 mm−1 |
| c = 11.414 (2) Å | T = 293 K |
| β = 108.03 (3)° | Block, colourless |
| V = 1041.2 (4) Å3 | 0.25 × 0.20 × 0.18 mm |
| Z = 4 |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.018 |
| Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 1.9° |
| graphite | h = −14→14 |
| ω scans | k = −11→11 |
| 4554 measured reflections | l = −14→14 |
| 2393 independent reflections | 3 standard reflections every 100 reflections |
| 2214 reflections with I > 2σ(I) | intensity decay: none |
| 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) = 0.119 | H-atom parameters constrained |
| S = 1.30 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.3194P] where P = (Fo2 + 2Fc2)/3 |
| 2393 reflections | (Δ/σ)max < 0.001 |
| 127 parameters | Δρmax = 0.30 e Å−3 |
| 0 restraints | Δρmin = −0.46 e Å−3 |
| C11H14N2S | V = 1041.2 (4) Å3 |
| Mr = 206.30 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 11.195 (2) Å | µ = 0.27 mm−1 |
| b = 8.5694 (17) Å | T = 293 K |
| c = 11.414 (2) Å | 0.25 × 0.20 × 0.18 mm |
| β = 108.03 (3)° |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.018 |
| 4554 measured reflections | θmax = 27.5° |
| 2393 independent reflections | 3 standard reflections every 100 reflections |
| 2214 reflections with I > 2σ(I) | intensity decay: none |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.119 | Δρmax = 0.30 e Å−3 |
| S = 1.30 | Δρmin = −0.46 e Å−3 |
| 2393 reflections | Absolute structure: ? |
| 127 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | 0.50030 (4) | 0.12695 (5) | 0.27663 (4) | 0.01992 (15) | |
| N2 | 0.34546 (13) | 0.29432 (17) | 0.09833 (13) | 0.0162 (3) | |
| N1 | 0.53176 (13) | 0.23342 (19) | 0.06683 (13) | 0.0183 (3) | |
| H1A | 0.4979 | 0.2678 | −0.0068 | 0.022* | |
| C7 | 0.45718 (15) | 0.2256 (2) | 0.14190 (15) | 0.0152 (3) | |
| C5 | 0.66016 (16) | 0.1894 (2) | 0.10058 (16) | 0.0177 (4) | |
| C8 | 0.30485 (17) | 0.3898 (2) | −0.01429 (16) | 0.0200 (4) | |
| H8A | 0.2822 | 0.3248 | −0.0874 | 0.024* | |
| H8B | 0.3704 | 0.4617 | −0.0182 | 0.024* | |
| C11 | 0.25255 (16) | 0.2964 (2) | 0.16519 (16) | 0.0203 (4) | |
| H11A | 0.2806 | 0.3614 | 0.2382 | 0.024* | |
| H11B | 0.2364 | 0.1919 | 0.1892 | 0.024* | |
| C4 | 0.70097 (18) | 0.0997 (2) | 0.01900 (18) | 0.0225 (4) | |
| H4A | 0.6439 | 0.0646 | −0.0541 | 0.027* | |
| C9 | 0.19114 (17) | 0.4771 (2) | −0.00189 (18) | 0.0245 (4) | |
| H9A | 0.1312 | 0.4984 | −0.0821 | 0.029* | |
| H9B | 0.2158 | 0.5748 | 0.0418 | 0.029* | |
| C6 | 0.74613 (17) | 0.2436 (2) | 0.20885 (17) | 0.0241 (4) | |
| H6A | 0.7196 | 0.3065 | 0.2624 | 0.029* | |
| C2 | 0.91276 (19) | 0.1125 (3) | 0.1562 (2) | 0.0337 (5) | |
| H2A | 0.9971 | 0.0854 | 0.1755 | 0.040* | |
| C3 | 0.82751 (19) | 0.0628 (2) | 0.0475 (2) | 0.0307 (5) | |
| H3A | 0.8551 | 0.0038 | −0.0075 | 0.037* | |
| C10 | 0.13624 (17) | 0.3649 (2) | 0.07178 (18) | 0.0243 (4) | |
| H10A | 0.0844 | 0.4197 | 0.1124 | 0.029* | |
| H10B | 0.0865 | 0.2841 | 0.0193 | 0.029* | |
| C1 | 0.87165 (18) | 0.2032 (3) | 0.23648 (19) | 0.0309 (5) | |
| H1B | 0.9289 | 0.2375 | 0.3098 | 0.037* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0211 (2) | 0.0247 (3) | 0.0136 (2) | 0.00322 (17) | 0.00489 (16) | 0.00532 (16) |
| N2 | 0.0159 (7) | 0.0202 (7) | 0.0125 (6) | 0.0012 (6) | 0.0045 (5) | 0.0028 (5) |
| N1 | 0.0162 (7) | 0.0264 (8) | 0.0124 (6) | 0.0025 (6) | 0.0049 (5) | 0.0027 (6) |
| C7 | 0.0164 (8) | 0.0160 (8) | 0.0127 (7) | −0.0019 (6) | 0.0036 (6) | −0.0021 (6) |
| C5 | 0.0180 (8) | 0.0180 (8) | 0.0175 (8) | 0.0006 (7) | 0.0060 (7) | 0.0036 (6) |
| C8 | 0.0204 (8) | 0.0248 (9) | 0.0150 (8) | 0.0033 (7) | 0.0056 (6) | 0.0049 (7) |
| C11 | 0.0174 (8) | 0.0270 (10) | 0.0181 (8) | −0.0008 (7) | 0.0078 (7) | 0.0009 (7) |
| C4 | 0.0254 (9) | 0.0195 (9) | 0.0248 (9) | 0.0001 (7) | 0.0108 (7) | −0.0009 (7) |
| C9 | 0.0204 (9) | 0.0264 (10) | 0.0264 (9) | 0.0051 (7) | 0.0070 (7) | 0.0076 (8) |
| C6 | 0.0223 (9) | 0.0304 (10) | 0.0192 (9) | −0.0014 (8) | 0.0057 (7) | 0.0016 (7) |
| C2 | 0.0200 (9) | 0.0385 (12) | 0.0436 (12) | 0.0075 (8) | 0.0111 (9) | 0.0164 (10) |
| C3 | 0.0298 (10) | 0.0266 (10) | 0.0423 (12) | 0.0080 (8) | 0.0206 (9) | 0.0029 (9) |
| C10 | 0.0176 (8) | 0.0299 (10) | 0.0262 (9) | 0.0017 (7) | 0.0078 (7) | 0.0028 (8) |
| C1 | 0.0201 (9) | 0.0415 (12) | 0.0264 (10) | −0.0039 (8) | 0.0002 (8) | 0.0098 (9) |
| S1—C7 | 1.6892 (17) | C4—C3 | 1.388 (3) |
| N2—C7 | 1.332 (2) | C4—H4A | 0.9300 |
| N2—C11 | 1.468 (2) | C9—C10 | 1.527 (3) |
| N2—C8 | 1.472 (2) | C9—H9A | 0.9700 |
| N1—C7 | 1.371 (2) | C9—H9B | 0.9700 |
| N1—C5 | 1.419 (2) | C6—C1 | 1.385 (3) |
| N1—H1A | 0.8600 | C6—H6A | 0.9300 |
| C5—C4 | 1.389 (2) | C2—C3 | 1.379 (3) |
| C5—C6 | 1.390 (3) | C2—C1 | 1.384 (3) |
| C8—C9 | 1.520 (2) | C2—H2A | 0.9300 |
| C8—H8A | 0.9700 | C3—H3A | 0.9300 |
| C8—H8B | 0.9700 | C10—H10A | 0.9700 |
| C11—C10 | 1.522 (3) | C10—H10B | 0.9700 |
| C11—H11A | 0.9700 | C1—H1B | 0.9300 |
| C11—H11B | 0.9700 | ||
| C7—N2—C11 | 123.08 (14) | C5—C4—H4A | 120.2 |
| C7—N2—C8 | 124.92 (14) | C8—C9—C10 | 103.46 (15) |
| C11—N2—C8 | 111.72 (13) | C8—C9—H9A | 111.1 |
| C7—N1—C5 | 125.40 (15) | C10—C9—H9A | 111.1 |
| C7—N1—H1A | 117.3 | C8—C9—H9B | 111.1 |
| C5—N1—H1A | 117.3 | C10—C9—H9B | 111.1 |
| N2—C7—N1 | 115.37 (15) | H9A—C9—H9B | 109.0 |
| N2—C7—S1 | 122.14 (13) | C1—C6—C5 | 119.56 (19) |
| N1—C7—S1 | 122.40 (13) | C1—C6—H6A | 120.2 |
| C4—C5—C6 | 119.98 (17) | C5—C6—H6A | 120.2 |
| C4—C5—N1 | 118.73 (16) | C3—C2—C1 | 119.36 (19) |
| C6—C5—N1 | 121.13 (16) | C3—C2—H2A | 120.3 |
| N2—C8—C9 | 103.50 (14) | C1—C2—H2A | 120.3 |
| N2—C8—H8A | 111.1 | C2—C3—C4 | 120.80 (19) |
| C9—C8—H8A | 111.1 | C2—C3—H3A | 119.6 |
| N2—C8—H8B | 111.1 | C4—C3—H3A | 119.6 |
| C9—C8—H8B | 111.1 | C11—C10—C9 | 103.05 (15) |
| H8A—C8—H8B | 109.0 | C11—C10—H10A | 111.2 |
| N2—C11—C10 | 103.34 (14) | C9—C10—H10A | 111.2 |
| N2—C11—H11A | 111.1 | C11—C10—H10B | 111.2 |
| C10—C11—H11A | 111.1 | C9—C10—H10B | 111.2 |
| N2—C11—H11B | 111.1 | H10A—C10—H10B | 109.1 |
| C10—C11—H11B | 111.1 | C2—C1—C6 | 120.7 (2) |
| H11A—C11—H11B | 109.1 | C2—C1—H1B | 119.6 |
| C3—C4—C5 | 119.51 (18) | C6—C1—H1B | 119.6 |
| C3—C4—H4A | 120.2 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···S1i | 0.86 | 2.64 | 3.4359 (17) | 155 |
| Symmetry codes: (i) x, −y+1/2, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···S1i | 0.86 | 2.64 | 3.4359 (17) | 155 |
| Symmetry codes: (i) x, −y+1/2, z−1/2. |
Casas, J. S., Castano, M. V. & Castellano, E. E. (2002). Inorg. Chem. 41, 1550–1557.
Cowley, A. R., Dilworth, J. R. & Dorinelly, P. S. (2002). J. Am. Chem. Soc. 124, 5270–5271.
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Toshiaki, M., Hideo, A. & Yoshiharu, Y. (2003). J. Org. Chem. 68, 8514–8519.
Thioamides have received considerable attention in the literature. They are attractive from several points of view in application (Toshiaki et al., 2003). As part of our search for new thioamide compounds we synthesized the title compound (I), and describe its structure here.
In (I) (Fig. 1), the C6—S1 bond length of 1.689 (2)Å is comparable with C—S bond [1.688 (2) Å] reported (Cowley et al., 2002). The distance of N1—C6 [1.332 (2) Å] is similar to the distance of reported [1.349 (1) Å] (Casas et al., 2002). The crystal strucure is stabilized by intermolecular C—H···S interactions.