Z Kristallogr NCS 2016; 231(4) 1051–1052 Open Access Gamal A El Hiti*, Bakr F Abdel Wahab, Mohammed Baashen and Hazem A Ghabbour Crystal structure of ethyl 5 amino 3 (methylthio) 1 (1 phenyl 5 (thioph[.]
Z Kristallogr NCS 2016; 231(4): 1051–1052 Open Access Gamal A El-Hiti*, Bakr F Abdel-Wahab, Mohammed Baashen and Hazem A Ghabbour Crystal structure of ethyl 5-amino-3-(methylthio)1-(1-phenyl-5-(thiophen-2-yl)-1H-pyrazole-3-carbonyl)-1H-pyrazole-4-carboxylate, C21H19N5O3S2 Table 1: Data collection and handling Crystal: Wavelength: µ: Diffractometer, scan mode: 2θmax , completeness: N(hkl)measured , N(hkl)unique , Rint : Criterion for Iobs , N(hkl)gt : N(param)refined : Programs: DOI 10.1515/ncrs-2016-0046 Received February 5, 2016; accepted May 18, 2016; available online June 1, 2016 Abstract C21 H19 N5 O3 S2 , monoclinic, P21 /c (No 14), a = 24.7576(12) Å, b = 5.0596(2) Å, c = 16.9165(8) Å, β = 101.630(2)°, V = 2075.52(16) Å3 , Z = 4, Rgt (F) = 0.0427, wRref (F ) = 0.1040, T = 100 K CCDC no.: 1443918 The crystal structure is shown in the figure Tables and contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters *Corresponding author: Gamal A El-Hiti, Cornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, P.O Box 10219, Riyadh 11433, Saudi Arabia, e-mail: gelhiti@ksu.edu.sa Bakr F Abdel-Wahab: Department of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia; and Applied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt Mohammed Baashen: Department of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia Hazem A Ghabbour: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O Box 2457, Riyadh 11451, Saudi Arabia; and Faculty of Pharmacy, Department of Medicinal Chemistry, University of Mansoura, Mansoura 35516, Egypt Colourless needle Size 0.86 × 0.23 × 0.05 mm Mo K α radiation (0.71073 Å) 2.9 cm−1 Bruker APEX-II, φ and ω 52.2°, >99% 29436, 3623, 0.086 Iobs > σ(Iobs ), 2766 290 SHELX [4], Bruker programs [5] Table 2: Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2 ) Atom S1 S2 O1 O2 O3 N1 N2 N3 N4 N5 C1 H1A C2 H2A C3 H3A C4 C5 C6 H6A C7 C8 C9 C10 C11 C12 C13 H13A x y z Uiso */Ueq −0.79753(3) −0.17076(13) 0.42519(4) 0.0236(2) −0.61383(3) −1.07683(12) 0.52294(4) 0.01806(18) −0.75167(7) −0.9039(3) 0.77827(10) 0.0236(4) −0.58957(7) −1.5987(3) 0.75605(10) 0.0195(4) −0.55928(7) −1.4877(3) 0.64286(9) 0.0182(4) −0.84091(8) −0.3677(4) 0.63459(11) 0.0129(5) −0.81784(8) −0.5509(4) 0.68870(11) 0.0153(5) −0.69809(8) −0.9648(4) 0.68660(11) 0.0134(5) −0.68408(8) −0.9041(4) 0.61265(11) 0.0146(5) −0.67289(10) −1.2746(5) 0.79543(13) 0.0199(5) −0.83170(11) 0.1002(5) 0.38090(15) 0.0219(6) −0.8288 0.1628 0.3302 0.026* −0.86322(11) 0.2132(5) 0.42727(14) 0.0175(6) −0.8846 0.3628 0.4122 0.021* −0.86036(10) 0.0789(5) 0.50214(14) 0.0147(6) −0.8796 0.1315 0.5413 0.018* −0.82607(10) −0.1364(5) 0.50994(14) 0.0133(6) −0.81039(10) −0.3250(5) 0.57580(14) 0.0128(5) −0.76617(10) −0.4932(5) 0.59329(14) 0.0131(5) −0.7380 −0.5131 0.5648 0.016* −0.77235(10) −0.6293(5) 0.66346(14) 0.0138(6) −0.74090(10) −0.8372(5) 0.71411(14) 0.0156(6) −0.66742(10) −1.1732(5) 0.72440(14) 0.0143(6) −0.63237(10) −1.2498(5) 0.67460(14) 0.0146(5) −0.64483(10) −1.0742(5) 0.60677(14) 0.0149(6) −0.59292(10) −1.4611(5) 0.69548(14) 0.0157(6) −0.51516(11) −1.6832(5) 0.66408(15) 0.0212(6) −0.5305 −1.8598 0.6633 0.025* © 2016 Gamal A El-Hiti et al., published by De Gruyter This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License Unauthenticated Download Date | 2/8/17 6:33 PM 1052 | El-Hiti et al.: C21 H19 N5 O3 S2 Table (continued) Atom x y z Uiso */Ueq H13B C14 H14A H14B H14C C15 H15A H15B H15C C16 C17 H17A C18 H18A C19 H19A C20 H20A C21 H21A H2N5 H1N5 −0.4937 −0.47994(12) −0.4506 −0.4647 −0.5018 −0.64827(11) −0.6329 −0.6433 −0.6869 −0.89186(10) −0.89276(11) −0.8608 −0.94180(11) −0.9427 −0.98946(11) −1.0222 −0.98796(11) −1.0198 −0.93902(11) −0.9380 −0.6961(12) −0.6525(13) −1.6485 −1.6592(6) −1.7862 −1.4843 −1.6917 −0.7991(5) −0.7677 −0.6450 −0.8368 −0.2494(5) −0.0911(5) −0.0640 0.0283(5) 0.1364 −0.0117(5) 0.0695 −0.1728(5) −0.2006 −0.2936(5) −0.4033 −1.207(5) −1.403(6) 0.7176 0.60266(18) 0.6139 0.6046 0.5499 0.46764(15) 0.4207 0.5014 0.4514 0.64389(14) 0.70933(15) 0.7481 0.71700(16) 0.7612 0.65957(16) 0.6649 0.59430(16) 0.5555 0.58631(16) 0.5425 0.8206(16) 0.8072(18) 0.025* 0.0355(8) 0.053* 0.053* 0.053* 0.0216(6) 0.032* 0.032* 0.032* 0.0136(6) 0.0210(6) 0.025* 0.0268(7) 0.032* 0.0233(6) 0.028* 0.0247(7) 0.030* 0.0224(6) 0.027* 0.026(8)* 0.035(10)* Source of material Reaction of 1-phenyl-5-(thiophen-2-yl)-1H-pyrazole-3-carbohydrazide and ethyl 2-cyano-3,3-bis(methylthio)acrylate in anhydrous ethanol under reflux for h gave the crude product which was recrystallized from dimethylformamide to give colorless crystals (Mp: 194–195°C) of the title compound Experimental details Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2U eq (C) The H atoms of the methyl group were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite [4]), with U iso (H) set to 1.5U eq (O) Discussion Bis-pyrazoles have received great attention since they show various interesting applications [1–3] Cell refinement and data reduction were carried out by Bruker SAINT [5] The asymmetric unit contains only one independent molecule The phenyl ring (C16—C21) is seriously deviated from the whole molecule plane and makes a dihedral angle of 47.46 (2)° with pyrazol ring (N1—N2—C5—C7) The packing structure shows at least two possible non-classical hydrogen bonds between C1—H1A· · · O1i and C1—H1A· · · N2i with symmetry code: (i) x, −y−1/2, z−1/2 Acknowledgements: The authors extend their appreciation to the College of Applied Medical Sciences Research Centre and the Deanship of Scientific Research at King Saud University for their funding of this research References Abdel-Wahab, B F.; El-Ahl, A.-A S.: Synthesis and characterization of some new heterocycles incorporating the 1-phenyl5-(2-thienyl)pyrazole moiety Phosphorus, Sulfur Silicon Relat Elem 185 (2010) 249–260 Abdel-Aziz, S A.-G.; Ali, T E.; El-Mahdy, K M.; Abdel-Karim, S M.: Synthesis and antimicrobial activities of some novel bis-pyrazole derivatives containing a hydrophosphoryl unit Eur J Chem (2011) 25–35 Yavari, S.; Nasiri-Gheidari, S.; Taherpour, A.; Yavari, I.: Synthesis of alkyl bis(dimethylamino)methylenecarbamodithioates from 1,1,3,3-tetramethylguanidine, CS2 and oxiranes Chinese Chem Lett 23 (2012) 699–702 Sheldrick, G M.: A short history of SHELX Acta Crystallogr A64 (2008) 112–122 Bruker APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA, 2009 Unauthenticated Download Date | 2/8/17 6:33 PM ... −0 .4 033 ? ?1. 20 7 (5) ? ?1. 4 03( 6) 0. 717 6 0.6 026 6 (18 ) 0.6 13 9 0.6 046 0 . 54 99 0 .46 7 64( 15 ) 0. 42 0 7 0 .50 14 0. 4 51 4 0.6 43 8 9 ( 14 ) 0.70 933 ( 15 ) 0. 74 81 0. 717 00 (16 ) 0.7 6 12 0. 659 57 (16 ) 0.6 649 0 .59 43 0 (16 ) 0 .55 55 0 .58 6 31 (16 )... −0.69 61( 12) −0. 6 52 5( 13 ) ? ?1. 64 85 ? ?1. 659 2( 6) ? ?1. 78 62 ? ?1. 48 43 ? ?1. 6 917 −0.79 91 (5) −0.7677 −0.6 45 0 −0. 836 8 −0 . 24 94 (5) −0.0 911 (5) −0.0 640 0. 02 83 (5) 0. 13 6 4 −0. 011 7 (5) 0.06 95 −0 .17 28 (5) −0 .20 06 −0 .2 936 (5) ... 0 .58 6 31 (16 ) 0 . 54 25 0. 820 6 (16 ) 0.80 72 (18 ) 0.0 25 * 0.0 35 5 (8) 0. 0 53 * 0. 0 53 * 0. 0 53 * 0.0 21 6 (6) 0. 0 32 * 0. 0 32 * 0. 0 32 * 0.0 13 6 (6) 0.0 21 0 (6) 0.0 25 * 0. 026 8(7) 0. 0 32 * 0.0 23 3 (6) 0. 028 * 0. 0 24 7(7) 0. 030 * 0. 022 4( 6)