Z. Kristallogr. NCS 2016; 231(2): 473–474
Open Access Yahia N. Mabkhot*, Assem Barakat, Salim S. Al-Showiman, Saied M. Soliman, Wolfgang Frey and Hazem A. Ghabbour
Crystal structure of 2-(bis(methylthio)methylene)1-phenylbutane-1,3-dione, C13H14O2S2 Abstract ¯ C13 H14 O2 S2 , triclinic, P1 (no. 2) a = 8.0970(9) Å, b = 8.8152(10) Å, c = 9.8217(10) Å, α = 76.269(5)°, β = 69.539(4)°, γ = 82.065(5)°, ς = 636.87(12) Å3 , Z = 2, Rgt (F) = 0.028, wRref (F 2 ) = 0.073, T = 100 K. CCDC no.: 1030329 Table 1: Data collection and handling. Crystal:
Colourless, block, size 0.19×0.32×0.33 mm Mo K α radiation (0.71073 Å) 4.04 cm−1 Bruker Kappa APEXII Duo, ω + φ Scans 61.38° 14119, 3868 Iobs > 2 σ(Iobs ), 3559 158 SHELX [2]
Wavelength: µ: Diffractometer, scan mode:
DOI 10.1515/ncrs-2015-0144 Received November 24, 2015; accepted January 13, 2016; available online February 16, 2016 *Corresponding author: Yahia N. Mabkhot, Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia, e-mail:
[email protected] Assem Barakat: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia; and Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt Salim S. Al-Showiman: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia Saied M. Soliman: Department of Chemistry, Rabigh College of Science and Art, King Abdulaziz University, P. O. Box 344, Rabigh 21911, Saudi Arabia; and Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, 21525 Alexandria, Egypt Wolfgang Frey: Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, Stuttgart 70569, Germany Hazem A. Ghabbour: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia; and Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
2θmax : N(hkl)measured , N(hkl)unique : Criterion for Iobs , N(hkl)gt : N(param)refined : Programs:
Table 2: Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2 ). Atom
Site
H(4A) H(4B) H(4C) H(5A) H(5B) H(5C) H(6A) H(6B) H(6C) H(9) H(10) H(11) H(12) H(13)
2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i
x
y
z
Uiso
0.2491 0.1170 0.0423 0.2126 0.3731 0.2815 0.5392 0.4295 0.3739 0.0516 −0.1048 0.0011 0.2599 0.4127
0.0307 0.0573 0.0660 0.6190 0.7158 0.7584 0.7199 0.8208 0.8332 0.3816 0.3679 0.2016 0.0420 0.0502
1.1194 1.0258 1.1978 0.6284 0.5086 0.6691 0.8437 0.9658 0.8222 0.7750 0.6181 0.4489 0.4403 0.6006
0.036 0.036 0.036 0.028 0.028 0.028 0.034 0.034 0.034 0.019 0.024 0.024 0.022 0.018
The crystal structure is shown in the figure. Tables 1–3 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.
© 2016 Yahia N. Mabkhot et al., published by De Gruyter. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.
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474 | Mabkhot et al.: C13 H14 O2 S2 Table 3: Atomic displacement parameters (Å2 ). Atom
Site
S(1) O(1) C(1) S(2) O(2) C(2) C(3) C(4) C(5) C(6) C(7) C(8) C(9) C(10) C(11) C(12) C(13)
2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i 2i
x
y
z
U11
U22
U33
U12
U13
U23
0.47192(3) 0.48294(9) 0.3348(1) 0.27711(3) 0.0998(1) 0.2826(1) 0.1689(1) 0.1420(2) 0.3170(1) 0.4214(2) 0.3505(1) 0.2484(1) 0.0936(1) 0.0012(1) 0.0636(1) 0.2175(1) 0.3087(1)
0.53629(3) 0.13478(8) 0.4761(1) 0.60478(3) 0.34580(9) 0.3272(1) 0.2615(1) 0.0888(1) 0.6731(1) 0.7627(1) 0.2208(1) 0.2176(1) 0.3123(1) 0.3047(1) 0.2051(1) 0.1103(1) 0.1159(1)
0.68364(2) 0.79988(8) 0.8705(1) 0.99309(3) 1.15475(8) 0.9125(1) 1.0646(1) 1.1055(1) 0.6145(1) 0.8950(1) 0.8018(1) 0.7025(1) 0.7077(1) 0.6138(1) 0.5138(1) 0.5085(1) 0.6032(1)
0.0145(1) 0.0200(3) 0.0130(4) 0.0183(1) 0.0218(3) 0.0144(4) 0.0145(4) 0.0280(5) 0.0197(4) 0.0312(5) 0.0156(4) 0.0144(4) 0.0163(4) 0.0190(4) 0.0239(5) 0.0234(5) 0.0169(4)
0.0137(1) 0.0168(3) 0.0143(4) 0.0159(1) 0.0251(4) 0.0145(4) 0.0189(4) 0.0203(5) 0.0178(4) 0.0164(4) 0.0120(4) 0.0123(4) 0.0147(4) 0.0197(4) 0.0209(5) 0.0181(4) 0.0137(4)
0.0139(1) 0.0240(4) 0.0128(4) 0.0167(1) 0.0155(3) 0.0125(4) 0.0145(4) 0.0195(5) 0.0158(4) 0.0241(5) 0.0133(4) 0.0120(4) 0.0165(4) 0.0222(5) 0.0189(4) 0.0155(4) 0.0149(4)
−0.00036(8) 0.0033(3) 0.0006(3) −0.00002(8) −0.0029(3) −0.0007(3) −0.0029(3) −0.0084(4) 0.0010(3) −0.0060(4) −0.0026(3) −0.0018(3) 0.0000(3) 0.0025(3) −0.0015(4) −0.0014(3) 0.0003(3)
−0.00109(8) −0.0099(3) −0.0033(3) −0.00414(9) −0.0012(3) −0.0038(3) −0.0044(3) −0.0018(4) −0.0048(3) −0.0130(4) −0.0034(3) −0.0027(3) −0.0040(3) −0.0090(4) −0.0108(4) −0.0060(3) −0.0040(3)
−0.00290(8) −0.0076(3) −0.0046(3) −0.00792(8) −0.0067(3) −0.0039(3) −0.0024(3) −0.0008(4) −0.0014(3) −0.0042(4) −0.0027(3) −0.0027(3) −0.0048(3) −0.0051(4) −0.0037(3) −0.0062(3) −0.0043(3)
Source of material
Discussion
The reagents and solvents used in this study are commercially available. The synthesis of (bis(methylthio)methylene)1-phenylbutane-1,3-dione was carried out according to following procedure: A solution of dimethylformamide (40 mL) and 1.62 g (0.01 mol) of 1-phenylbutane-1,3-dione, and 5 g of K2 CO3 were treated drop wise with 1 mL of carbon disulphide for 1 h at 25 °C with stirring. This mixture was further stirred for 1 h with 82 g (0.02 mol) of iodomethane, continued for further 3 h and the reaction mixture was poured into ice-water. The precipitated product was filtered and dried; the precipitated was recrystallized from ethanol. Yield: 86%; m.p. 55 °C; IR (νmax ): 3054, 2991, 2926, 1646, 1578, 1423, 1262 cm−1 ; 1 H-NMR (400 MHz, CDCl3 ): δ 2.17 (s, 3H, CH3 ), 2.23 (s, 3H, CH3 ), 2.50 (s, 3H, CH3 ), 7.28–7.92 (m, 10H, Ph); 13 C-NMR (100 MHz, DMSO-d6 ): δ 18.5, 18.9, 28.9, 128.9, 129.6, 135.0, 138.9, 140.1, 155.4, 194.6; MS m/z (%): 266.04 [M+ , 60%]; Anal. calcd. for C13 H14 O2 S2 : C, 58.62; H, 5.30; S, 24.07%; Found: C, 58.61; H, 5.31; S, 24.10%.
Impressive biological properties displayed by privileged nucleus of ketene N,N- and N,S-acetals have triggered the development of a variety of methods for their synthesis [1]. The crystal structure of target compound consist of six membered ring (C8—C13) which is bonded to the ketene S,S-dithioacetal moiety. The molecules packing in the crystal structure is stabilized by two intermolecular hydrogen bonds.
Acknowledgements: The authors extend their sincere appreciation to the Deanship of Scientific Research at king Saud University for its funding this Prolific Research group (PRG-1437-29).
References 1. Sommen, G.; Comel, A.; Kirsch, G.: A convenient synthesis of 2,3,4,5-functionalised thieno[2,3-b]thiophenes. Synthesis 5 (2003) 735–741. 2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112—122.
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