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access1,3-Bis(1-cyclohexylethyl)imidazolidine-2-thione
aDepartment of Chemistry, University of Malakand, Pakistan, bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and cDepartment of Pharmacy, University of Malakand, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
The complete molecule of the title compound, C19H34N2S, is generated by crystallographic twofold symmetry, with the C=S group lying on the rotation axis. A short C—H⋯S contact occurs in the molecule. The five-membered ring is twisted and the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean plane of the five-membered ring and the basal plane of the cyclohexyl ring is 75.32 (13)°.
![[Scheme 1]](hb6637scheme1.gif)
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2007![[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]](../../../../../../logos/arrows/e_arr.gif "Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.")
); cell SAINT (Bruker, 2007); 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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536812006150/hb6637sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536812006150/hb6637Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812006150/hb6637Isup3.cml
(S)-1-cyclohexylethanamine (2.5 equiv.) and 1,2-dibromoethane (1 equiv.) were placed in a pressure vessel and heated at 393 K for 5 h, during which the reaction mixture solidified. The system was cooled to room temperature and NaOH (1 N, 20 ml) and ethyl acetate (20 ml) were added in to the reaction mixture. After dissolving the reaction mixture, the crude product was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were concentrated and subjected to The product obtained from (1 equiv.) was added to toluene (0.4 M) in pressure vessel and thiocarbonyldiimidazol (1.1 equiv.) was added to it. This mixture was heated about 373 K for 15 h. Again the extraction with ethyl acetate (3 × 25 ml) was carried out by using to get the required product. Yield: 90%. Colourless prisms of (I) were obtained by recrystallizing from methanol after 48 h.
The H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for all other H atoms.
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./hb6637fig1thm.gif) | Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted lines indicate the short C—H···S contacts. |
| C19H34N2S | Dx = 1.070 Mg m−3 |
| Mr = 322.54 | Mo Kα radiation, λ = 0.71073 Å |
| Tetragonal, P41212 | Cell parameters from 1358 reflections |
| Hall symbol: P 4abw 2nw | θ = 3.0–28.3° |
| a = 6.1008 (3) Å | µ = 0.16 mm−1 |
| c = 53.790 (2) Å | T = 296 K |
| V = 2002.04 (17) Å3 | Prism, colourless |
| Z = 4 | 0.30 × 0.25 × 0.20 mm |
| F(000) = 712 |
| Bruker Kappa APEXII CCD diffractometer | 2500 independent reflections |
| Radiation source: fine-focus sealed tube | 1357 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.047 |
| Detector resolution: 7.50 pixels mm-1 | θmax = 28.3°, θmin = 3.0° |
| ω scans | h = −8→4 |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −7→8 |
| Tmin = 0.957, Tmax = 0.966 | l = −71→65 |
| 18805 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
| wR(F2) = 0.176 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.4327P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 2500 reflections | Δρmax = 0.12 e Å−3 |
| 102 parameters | Δρmin = −0.12 e Å−3 |
| 0 restraints | Absolute structure: Flack (1983), with 874 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.0 (2) |
| C19H34N2S | Z = 4 |
| Mr = 322.54 | Mo Kα radiation |
| Tetragonal, P41212 | µ = 0.16 mm−1 |
| a = 6.1008 (3) Å | T = 296 K |
| c = 53.790 (2) Å | 0.30 × 0.25 × 0.20 mm |
| V = 2002.04 (17) Å3 |
| Bruker Kappa APEXII CCD diffractometer | 2500 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1357 reflections with I > 2σ(I) |
| Tmin = 0.957, Tmax = 0.966 | Rint = 0.047 |
| 18805 measured reflections |
| R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
| wR(F2) = 0.176 | Δρmax = 0.12 e Å−3 |
| S = 1.04 | Δρmin = −0.12 e Å−3 |
| 2500 reflections | Absolute structure: Flack (1983), with 874 Friedel pairs |
| 102 parameters | Absolute structure parameter: 0.0 (2) |
| 0 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.56724 (12) | 0.56724 (12) | 0.0000 | 0.0822 (4) | |
| N1 | 0.2683 (4) | 0.2943 (4) | 0.02021 (4) | 0.0735 (7) | |
| C1 | 0.3729 (4) | 0.3729 (4) | 0.0000 | 0.0652 (10) | |
| C2 | 0.0922 (6) | 0.1442 (6) | 0.01337 (5) | 0.0868 (10) | |
| H2A | −0.0500 | 0.2138 | 0.0149 | 0.104* | |
| H2B | 0.0950 | 0.0131 | 0.0236 | 0.104* | |
| C3 | 0.2873 (5) | 0.3852 (5) | 0.04524 (5) | 0.0696 (8) | |
| H3 | 0.4132 | 0.4849 | 0.0451 | 0.083* | |
| C4 | 0.0864 (7) | 0.5222 (6) | 0.05128 (8) | 0.1131 (13) | |
| H4A | 0.1147 | 0.6093 | 0.0658 | 0.170* | |
| H4B | −0.0361 | 0.4273 | 0.0544 | 0.170* | |
| H4C | 0.0537 | 0.6167 | 0.0375 | 0.170* | |
| C5 | 0.3390 (5) | 0.2040 (5) | 0.06392 (4) | 0.0652 (8) | |
| H5 | 0.2139 | 0.1032 | 0.0643 | 0.078* | |
| C6 | 0.5406 (6) | 0.0737 (6) | 0.05665 (6) | 0.0915 (10) | |
| H6A | 0.5139 | 0.0013 | 0.0409 | 0.110* | |
| H6B | 0.6630 | 0.1732 | 0.0544 | 0.110* | |
| C7 | 0.6000 (9) | −0.0961 (7) | 0.07594 (8) | 0.1415 (18) | |
| H7A | 0.4867 | −0.2075 | 0.0765 | 0.170* | |
| H7B | 0.7363 | −0.1666 | 0.0712 | 0.170* | |
| C8 | 0.6254 (10) | 0.0031 (7) | 0.10136 (8) | 0.147 (2) | |
| H8A | 0.6529 | −0.1123 | 0.1134 | 0.177* | |
| H8B | 0.7506 | 0.1011 | 0.1014 | 0.177* | |
| C9 | 0.4288 (10) | 0.1250 (8) | 0.10869 (7) | 0.1370 (18) | |
| H9A | 0.4537 | 0.1940 | 0.1247 | 0.164* | |
| H9B | 0.3070 | 0.0240 | 0.1105 | 0.164* | |
| C10 | 0.3709 (7) | 0.2961 (6) | 0.09005 (5) | 0.0976 (12) | |
| H10A | 0.4863 | 0.4054 | 0.0896 | 0.117* | |
| H10B | 0.2369 | 0.3685 | 0.0952 | 0.117* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0833 (6) | 0.0833 (6) | 0.0798 (7) | −0.0262 (6) | −0.0097 (5) | 0.0097 (5) |
| N1 | 0.0914 (18) | 0.0764 (16) | 0.0526 (12) | −0.0234 (13) | −0.0101 (12) | 0.0110 (12) |
| C1 | 0.0661 (15) | 0.0661 (15) | 0.063 (2) | −0.0067 (19) | −0.0152 (14) | 0.0152 (14) |
| C2 | 0.095 (2) | 0.099 (3) | 0.0666 (16) | −0.037 (2) | −0.0083 (16) | 0.0109 (16) |
| C3 | 0.086 (2) | 0.0616 (18) | 0.0614 (16) | −0.0014 (16) | −0.0048 (15) | 0.0017 (13) |
| C4 | 0.121 (3) | 0.091 (3) | 0.128 (3) | 0.026 (3) | −0.024 (3) | −0.017 (2) |
| C5 | 0.081 (2) | 0.0624 (16) | 0.0520 (14) | −0.0071 (15) | 0.0022 (14) | 0.0016 (13) |
| C6 | 0.109 (3) | 0.087 (2) | 0.079 (2) | 0.027 (2) | −0.0062 (19) | −0.0082 (18) |
| C7 | 0.181 (5) | 0.087 (3) | 0.157 (4) | 0.048 (3) | −0.061 (4) | −0.011 (3) |
| C8 | 0.238 (7) | 0.094 (3) | 0.110 (3) | 0.014 (4) | −0.088 (4) | 0.021 (2) |
| C9 | 0.219 (6) | 0.124 (4) | 0.068 (2) | −0.022 (4) | −0.019 (3) | 0.024 (2) |
| C10 | 0.144 (4) | 0.094 (2) | 0.0548 (16) | 0.008 (2) | 0.0080 (19) | −0.0014 (17) |
| S1—C1 | 1.677 (3) | C3—H3 | 0.9800 |
| N1—C1 | 1.349 (3) | C4—H4A | 0.9600 |
| N1—C2 | 1.458 (4) | C4—H4B | 0.9600 |
| N1—C3 | 1.461 (4) | C4—H4C | 0.9600 |
| C2—C2i | 1.506 (4) | C5—H5 | 0.9800 |
| C3—C4 | 1.519 (5) | C6—H6A | 0.9700 |
| C3—C5 | 1.527 (4) | C6—H6B | 0.9700 |
| C5—C6 | 1.516 (5) | C7—H7A | 0.9700 |
| C5—C10 | 1.526 (4) | C7—H7B | 0.9700 |
| C6—C7 | 1.510 (6) | C8—H8A | 0.9700 |
| C7—C8 | 1.503 (6) | C8—H8B | 0.9700 |
| C8—C9 | 1.465 (8) | C9—H9A | 0.9700 |
| C9—C10 | 1.490 (6) | C9—H9B | 0.9700 |
| C2—H2A | 0.9700 | C10—H10A | 0.9700 |
| C2—H2B | 0.9700 | C10—H10B | 0.9700 |
| C1—N1—C2 | 111.6 (2) | H4A—C4—H4C | 109.00 |
| C1—N1—C3 | 124.8 (2) | H4B—C4—H4C | 109.00 |
| C2—N1—C3 | 122.0 (2) | C3—C5—H5 | 108.00 |
| S1—C1—N1 | 125.87 (13) | C6—C5—H5 | 108.00 |
| S1—C1—N1i | 125.87 (13) | C10—C5—H5 | 108.00 |
| N1—C1—N1i | 108.3 (2) | C5—C6—H6A | 109.00 |
| N1—C2—C2i | 102.6 (3) | C5—C6—H6B | 109.00 |
| N1—C3—C4 | 110.0 (3) | C7—C6—H6A | 109.00 |
| N1—C3—C5 | 110.4 (2) | C7—C6—H6B | 109.00 |
| C4—C3—C5 | 115.1 (3) | H6A—C6—H6B | 108.00 |
| C3—C5—C6 | 112.2 (2) | C6—C7—H7A | 109.00 |
| C3—C5—C10 | 111.5 (3) | C6—C7—H7B | 109.00 |
| C6—C5—C10 | 109.1 (3) | C8—C7—H7A | 109.00 |
| C5—C6—C7 | 112.2 (3) | C8—C7—H7B | 109.00 |
| C6—C7—C8 | 111.9 (3) | H7A—C7—H7B | 108.00 |
| C7—C8—C9 | 111.4 (4) | C7—C8—H8A | 109.00 |
| C8—C9—C10 | 111.6 (4) | C7—C8—H8B | 109.00 |
| C5—C10—C9 | 113.1 (3) | C9—C8—H8A | 109.00 |
| N1—C2—H2A | 111.00 | C9—C8—H8B | 109.00 |
| N1—C2—H2B | 111.00 | H8A—C8—H8B | 108.00 |
| H2A—C2—H2B | 109.00 | C8—C9—H9A | 109.00 |
| C2i—C2—H2A | 111.00 | C8—C9—H9B | 109.00 |
| C2i—C2—H2B | 111.00 | C10—C9—H9A | 109.00 |
| N1—C3—H3 | 107.00 | C10—C9—H9B | 109.00 |
| C4—C3—H3 | 107.00 | H9A—C9—H9B | 108.00 |
| C5—C3—H3 | 107.00 | C5—C10—H10A | 109.00 |
| C3—C4—H4A | 109.00 | C5—C10—H10B | 109.00 |
| C3—C4—H4B | 109.00 | C9—C10—H10A | 109.00 |
| C3—C4—H4C | 109.00 | C9—C10—H10B | 109.00 |
| H4A—C4—H4B | 109.00 | H10A—C10—H10B | 108.00 |
| C2—N1—C1—S1 | 173.7 (2) | N1—C3—C5—C10 | 177.2 (3) |
| C2—N1—C1—N1i | −6.3 (3) | C4—C3—C5—C6 | 179.8 (3) |
| C3—N1—C1—S1 | 8.2 (4) | C4—C3—C5—C10 | −57.6 (4) |
| C3—N1—C1—N1i | −171.8 (2) | C3—C5—C6—C7 | 176.4 (3) |
| C1—N1—C2—C2i | 15.4 (3) | C10—C5—C6—C7 | 52.4 (4) |
| C3—N1—C2—C2i | −178.6 (3) | C3—C5—C10—C9 | −178.1 (4) |
| C1—N1—C3—C4 | 102.2 (3) | C6—C5—C10—C9 | −53.7 (4) |
| C1—N1—C3—C5 | −129.7 (3) | C5—C6—C7—C8 | −54.2 (5) |
| C2—N1—C3—C4 | −61.9 (4) | C6—C7—C8—C9 | 55.0 (5) |
| C2—N1—C3—C5 | 66.2 (3) | C7—C8—C9—C10 | −55.6 (5) |
| N1—C2—C2i—N1i | −17.5 (3) | C8—C9—C10—C5 | 56.3 (5) |
| N1—C3—C5—C6 | 54.5 (3) |
| Symmetry code: (i) y, x, −z. |
Experimental details
| Crystal data | |
| Chemical formula | C19H34N2S |
| Mr | 322.54 |
| Crystal system, space group | Tetragonal, P41212 |
| Temperature (K) | 296 |
| a, c (Å) | 6.1008 (3), 53.790 (2) |
| V (Å3) | 2002.04 (17) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.16 |
| Crystal size (mm) | 0.30 × 0.25 × 0.20 |
| Data collection | |
| Diffractometer | Bruker Kappa APEXII CCD diffractometer |
| Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
| Tmin, Tmax | 0.957, 0.966 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 18805, 2500, 1357 |
| Rint | 0.047 |
| (sin θ/λ)max (Å−1) | 0.667 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.176, 1.04 |
| No. of reflections | 2500 |
| No. of parameters | 102 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.12, −0.12 |
| Absolute structure | Flack (1983), with 874 Friedel pairs |
| Absolute structure parameter | 0.0 (2) |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Acknowledgements
The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors at Malakand University are also grateful for financial support provided by the Higher Education Commission (HEC), Islamabad, Pakistan.
References
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kazak, C., Yilmaz, V. T., Servi, S., Koca, M. & Heinemann, F. W. (2005). Acta Cryst. C61, o348–o350. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The title compound (I), (Fig. 1) has been synthesized as a part of our project related to imidazolidinethione.
The crystal structure of 1,3-dibenzoyl-4,5-dihydro-1H-imidazole-2(3H)-thione (Kazak et al., 2005) has been published which is related to the title compound (I), (Fig. 1).
The molecule has twofold symmetry about the C═S (C1═S1) of imidazolidinethione and therefore, the asymmetric unit is half of the molecule. The asymmetric part of imidazolidinethione moiety A (S1/C1/N1/C2) and the basal plane of cyclohexyl ring B (C6/C7/C9/C10) are almost planar with r.m.s. deviations of 0.036 and 0.004 Å, respectively. The dihedral angle between A/B is 75.32 (13)°. The cyclohexyl adopts chair conformation with apical C-atoms C5 and C8 at a distance of -0.651 (5) and 0.638 (8) Å, respectively from the basal plane B. There exist weak intramolecular H-bondings of C—H···S type (Table 1, Fig. 1) and form S(5) ring motif. No other interaction is found in the crystal.