#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206802.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2206802 loop_ _publ_author_name 'Cantalupo, Stefanie A.' 'Crundwell, Guy' _publ_section_title ; 1,2-Bis(3-methyl-2-thienyl)ethane-1,2-dione ; _journal_coeditor_code TK6247 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3079 _journal_page_last o3080 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C12 H10 O2 S2' _chemical_formula_moiety 'C12 H10 O2 S2' _chemical_formula_sum 'C12 H10 O2 S2' _chemical_formula_weight 250.34 _chemical_melting_point 343 _chemical_name_common ; 3,3'-dimethyl-2-thenil ; _chemical_name_systematic ; 1,2-Bis(3-methyl-2-thienyl)ethane-1,2-dione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 101.37(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.605(3) _cell_length_b 5.0901(16) _cell_length_c 12.193(4) _cell_measurement_reflns_used 3871 _cell_measurement_temperature 293 _cell_measurement_theta_max 29.6 _cell_measurement_theta_min 3.7 _cell_volume 584.4(3) _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2005) ; _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2005) ; _computing_data_reduction ; CrysAlis RED ; _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material CRYSTALS _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.876 _diffrn_measurement_device_type 'Oxford Diffraction Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3871 _diffrn_reflns_theta_full 22.3 _diffrn_reflns_theta_max 29.7 _diffrn_reflns_theta_min 4.3 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.436 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 260 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.21 _refine_diff_density_min -0.23 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 743 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.086 _refine_ls_R_factor_gt 0.047 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994; Prince, 1982) w = 1/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= F~calc~/F~max~ Method = Robust Weighting (Prince, 1982) W = w[1-(\dF/6\sF)^2^]^2^; A~i~ are: 0.352, 0.362, 0.186 and 0.0821 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.087 _refine_ls_wR_factor_gt 0.052 _refine_ls_wR_factor_ref 0.052 _reflns_number_gt 743 _reflns_number_total 1452 _reflns_threshold_expression I>3u(I) _[local]_cod_data_source_file tk6247.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2206802 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_type_symbol S1 1.09519(9) 0.1944(2) 0.70322(8) 0.0574 Uani 1.0000 S C2 0.9456(3) 0.2265(7) 0.5971(3) 0.0440 Uani 1.0000 C O1 0.8237(2) 0.4454(6) 0.4367(2) 0.0713 Uani 1.0000 O C1 0.9344(3) 0.4180(7) 0.5058(3) 0.0477 Uani 1.0000 C C3 0.8393(3) 0.0519(7) 0.6123(3) 0.0478 Uani 1.0000 C C6 0.6942(4) 0.0273(9) 0.5380(3) 0.0639 Uani 1.0000 C H7 0.6451 0.1922 0.5355 0.0500 Uiso 1.0000 H H8 0.6408 -0.1066 0.5657 0.0500 Uiso 1.0000 H H6 0.7045 -0.0182 0.4628 0.0500 Uiso 1.0000 H C4 0.8824(4) -0.1061(8) 0.7075(3) 0.0598 Uani 1.0000 C H4 0.8255 -0.2355 0.7309 0.0500 Uiso 1.0000 H C5 1.0166(4) -0.0492(9) 0.7647(3) 0.0644 Uani 1.0000 C H5 1.0614 -0.1330 0.8295 0.0500 Uiso 1.0000 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0440(5) 0.0636(6) 0.0555(5) -0.0021(5) -0.0123(3) 0.0092(5) C2 0.0380(16) 0.051(2) 0.0393(16) 0.0008(15) -0.0016(12) -0.0051(15) O1 0.0466(14) 0.087(2) 0.0671(16) -0.0163(14) -0.0225(12) 0.0252(15) C1 0.0422(17) 0.053(2) 0.0421(17) -0.0064(16) -0.0048(14) -0.0024(17) C3 0.0425(17) 0.054(2) 0.0448(17) -0.0004(16) 0.0024(13) -0.0062(17) C6 0.047(2) 0.080(3) 0.060(2) -0.017(2) -0.0013(17) -0.001(2) C4 0.052(2) 0.061(3) 0.066(2) -0.0042(18) 0.0102(17) 0.011(2) C5 0.057(2) 0.070(3) 0.060(2) 0.001(2) -0.0043(18) 0.023(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C2 . 1.741(3) yes S1 C5 . 1.701(4) yes C2 C1 . 1.468(5) yes C2 C3 . 1.394(5) yes O1 C1 . 1.227(4) yes C1 C1 2_766 1.542(6) yes C3 C4 . 1.405(5) yes C3 C6 . 1.511(5) yes C6 H7 . 0.961 no C6 H8 . 0.955 no C6 H6 . 0.969 no C4 H4 . 0.935 no C4 C5 . 1.370(5) yes C5 H5 . 0.927 no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle _geom_angle_publ_flag C2 S1 C5 . 91.31(17) yes S1 C2 C1 . 123.6(2) yes S1 C2 C3 . 111.1(3) yes C1 C2 C3 . 125.3(3) yes C1 C1 O1 2_766 119.3(4) yes C1 C1 C2 2_766 119.3(3) yes C2 C1 O1 . 121.4(3) yes C2 C3 C4 . 111.8(3) yes C2 C3 C6 . 125.9(3) yes C6 C3 C4 . 122.3(3) yes C3 C6 H7 . 109.630 no C3 C6 H8 . 110.085 no H7 C6 H8 . 109.874 no C3 C6 H6 . 109.473 no H7 C6 H6 . 108.633 no H8 C6 H6 . 109.121 no C3 C4 H4 . 124.075 no C3 C4 C5 . 113.2(3) yes H4 C4 C5 . 122.756 no S1 C5 C4 . 112.6(3) yes C4 C5 H5 . 124.675 no S1 C5 H5 . 122.682 no _cod_database_fobs_code 2206802