#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229358.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_2229358 loop_ _publ_author_name 'Lytvyn, Roman' 'Horak, Yuri' 'Matiychuk, Vasyl' 'Obushak, Mykola' 'Kinzhybalo, Vasyl' _publ_section_title ; 1-{5-[2-Chloro-5-(trifluoromethyl)phenyl]thiophen-2-yl}ethanone ; _journal_coeditor_code DS2088 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o585 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac 'C13 H8 Cl F3 O S' _chemical_formula_moiety 'C13 H8 Cl F3 O S' _chemical_formula_sum 'C13 H8 Cl F3 O S' _chemical_formula_weight 304.70 _chemical_melting_point 347 _chemical_name_systematic ; 1-{5-[2-Chloro-5-(trifluoromethyl)phenyl]thiophen-2-yl}ethanone ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 93.72(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.330(6) _cell_length_b 10.809(4) _cell_length_c 7.676(3) _cell_measurement_reflns_used 11592 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 33.92 _cell_measurement_theta_min 2.28 _cell_volume 1269.2(8) _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measurement_device_type 'Kuma KM-4-CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 16021 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 33.77 _diffrn_reflns_theta_min 3.26 _exptl_absorpt_coefficient_mu 0.49 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; (CrysAlis RED; Oxford Diffraction, 2006) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.487 _refine_diff_density_min -0.247 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 4377 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0909 _refine_ls_wR_factor_ref 0.0966 _reflns_number_gt 3093 _reflns_number_total 4377 _reflns_threshold_expression I>2sigma(I) _[local]_cod_data_source_file ds2088.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 1269.3(8) _cod_database_code 2229358 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl1 0.09807(2) 0.28619(3) 1.05277(5) 0.02440(10) Uani d . 1 . . S S1 0.37102(2) 0.42596(3) 1.04508(5) 0.01971(9) Uani d . 1 . . O O1 0.54239(7) 0.39388(9) 1.24469(14) 0.0261(2) Uani d . 1 . . C C2 0.42729(9) 0.29067(12) 1.08963(19) 0.0181(3) Uani d . 1 . . C C21 0.51398(9) 0.29623(12) 1.18365(19) 0.0208(3) Uani d . 1 . . C C22 0.56531(10) 0.17781(14) 1.1983(2) 0.0276(3) Uani d . 1 . . H H22A 0.5812 0.1521 1.0821 0.041 Uiso calc R 1 . . H H22B 0.5297 0.1133 1.2485 0.041 Uiso calc R 1 . . H H22C 0.6185 0.1909 1.2738 0.041 Uiso calc R 1 . . C C3 0.37969(9) 0.18899(12) 1.02942(19) 0.0194(3) Uani d . 1 . . H H3 0.4000 0.1062 1.0413 0.023 Uiso calc R 1 . . C C4 0.29753(9) 0.22147(12) 0.94833(19) 0.0192(3) Uani d . 1 . . H H4 0.2562 0.1630 0.9010 0.023 Uiso calc R 1 . . C C5 0.28396(9) 0.34750(11) 0.94559(18) 0.0160(3) Uani d . 1 . . C C51 0.20972(9) 0.41760(11) 0.86157(18) 0.0164(3) Uani d . 1 A . C C52 0.12277(9) 0.39514(12) 0.89694(18) 0.0179(3) Uani d . 1 . . C C53 0.05343(9) 0.45875(12) 0.81028(19) 0.0192(3) Uani d . 1 . . H H53 -0.0051 0.4413 0.8357 0.023 Uiso calc R 1 . . C C54 0.07070(9) 0.54733(12) 0.68726(19) 0.0198(3) Uani d . 1 . . H H54 0.0241 0.5907 0.6270 0.024 Uiso calc R 1 . . C C55 0.15699(9) 0.57247(12) 0.65236(18) 0.0192(3) Uani d . 1 A . C C1 0.17567(10) 0.66394(15) 0.5124(2) 0.0289(4) Uani d . 1 . . F F1 0.2540(6) 0.7124(13) 0.528(2) 0.049(3) Uani d P 0.49(3) A 1 F F2 0.1209(7) 0.7645(7) 0.5195(13) 0.0485(17) Uani d P 0.49(3) A 1 F F3 0.1634(9) 0.6244(10) 0.3552(8) 0.059(2) Uani d P 0.49(3) A 1 F F1A 0.2471(7) 0.7292(12) 0.549(2) 0.052(2) Uani d P 0.51(3) A 2 F F2A 0.1125(5) 0.7352(16) 0.465(2) 0.070(3) Uani d P 0.51(3) A 2 F F3A 0.1942(11) 0.5975(8) 0.3643(11) 0.079(2) Uani d P 0.51(3) A 2 C C56 0.22588(9) 0.50955(12) 0.73913(18) 0.0189(3) Uani d . 1 . . H H56 0.2843 0.5290 0.7153 0.023 Uiso calc R 1 A . 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 Cl1 0.01931(18) 0.02759(17) 0.0267(2) -0.00030(13) 0.00436(14) 0.00743(14) S1 0.01739(17) 0.01659(14) 0.0246(2) -0.00050(12) -0.00288(13) 0.00172(13) O1 0.0217(5) 0.0253(5) 0.0307(6) -0.0040(4) -0.0041(5) 0.0034(4) C2 0.0151(6) 0.0200(6) 0.0193(7) 0.0012(5) 0.0017(5) 0.0023(5) C21 0.0178(7) 0.0234(6) 0.0214(8) -0.0002(5) 0.0024(6) 0.0072(5) C22 0.0194(7) 0.0266(7) 0.0362(10) 0.0026(6) -0.0034(7) 0.0065(6) C3 0.0184(7) 0.0194(6) 0.0208(7) 0.0027(5) 0.0033(6) 0.0005(5) C4 0.0201(7) 0.0185(6) 0.0189(7) -0.0012(5) 0.0009(6) -0.0014(5) C5 0.0154(6) 0.0177(5) 0.0149(7) -0.0002(5) 0.0009(5) -0.0005(5) C51 0.0164(6) 0.0170(5) 0.0158(7) 0.0011(5) 0.0002(5) -0.0031(5) C52 0.0185(7) 0.0190(5) 0.0163(7) 0.0000(5) 0.0009(5) -0.0009(5) C53 0.0138(6) 0.0234(6) 0.0203(7) 0.0012(5) 0.0007(5) -0.0041(5) C54 0.0182(7) 0.0217(6) 0.0190(7) 0.0028(5) -0.0027(6) -0.0021(5) C55 0.0200(7) 0.0200(6) 0.0174(7) 0.0005(5) 0.0005(5) 0.0003(5) C1 0.0219(8) 0.0343(8) 0.0300(9) 0.0007(6) -0.0013(7) 0.0102(7) F1 0.015(2) 0.068(5) 0.062(5) 0.000(3) -0.003(2) 0.043(4) F2 0.050(3) 0.038(2) 0.059(4) 0.0255(18) 0.020(2) 0.0291(19) F3 0.115(6) 0.043(3) 0.0173(15) -0.024(3) -0.005(2) 0.0037(17) F1A 0.053(5) 0.049(3) 0.053(3) -0.029(3) -0.008(3) 0.022(2) F2A 0.0206(16) 0.093(6) 0.099(7) 0.016(3) 0.010(3) 0.074(5) F3A 0.160(6) 0.051(2) 0.029(2) 0.010(4) 0.037(3) 0.0148(18) C56 0.0169(7) 0.0211(6) 0.0189(7) -0.0004(5) 0.0018(5) -0.0017(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 S1 C2 . . 91.94(7) ? C3 C2 C21 . . 129.54(12) ? C3 C2 S1 . . 111.25(11) ? C21 C2 S1 . . 119.20(10) ? O1 C21 C2 . . 120.70(13) ? O1 C21 C22 . . 122.31(14) ? C2 C21 C22 . . 116.98(12) ? C21 C22 H22A . . 109.5 ? C21 C22 H22B . . 109.5 ? H22A C22 H22B . . 109.5 ? C21 C22 H22C . . 109.5 ? H22A C22 H22C . . 109.5 ? H22B C22 H22C . . 109.5 ? C2 C3 C4 . . 112.70(12) ? C2 C3 H3 . . 123.7 ? C4 C3 H3 . . 123.7 ? C5 C4 C3 . . 112.45(12) ? C5 C4 H4 . . 123.8 ? C3 C4 H4 . . 123.8 ? C4 C5 C51 . . 128.60(12) ? C4 C5 S1 . . 111.66(10) ? C51 C5 S1 . . 119.62(10) ? C52 C51 C56 . . 117.75(12) ? C52 C51 C5 . . 122.83(12) ? C56 C51 C5 . . 119.41(12) ? C53 C52 C51 . . 121.81(13) ? C53 C52 Cl1 . . 117.91(11) ? C51 C52 Cl1 . . 120.28(11) ? C54 C53 C52 . . 119.50(13) ? C54 C53 H53 . . 120.3 ? C52 C53 H53 . . 120.3 ? C53 C54 C55 . . 119.52(13) ? C53 C54 H54 . . 120.2 ? C55 C54 H54 . . 120.2 ? C56 C55 C54 . . 120.92(13) ? C56 C55 C1 . . 119.42(13) ? C54 C55 C1 . . 119.58(13) ? F3 C1 F1 . . 107.4(8) ? F2A C1 F1A . . 110.1(7) ? F3 C1 F2 . . 104.4(6) ? F1 C1 F2 . . 103.8(7) ? F2A C1 F3A . . 105.6(6) ? F1A C1 F3A . . 103.8(8) ? F2A C1 C55 . . 115.3(4) ? F3 C1 C55 . . 115.5(4) ? F1 C1 C55 . . 114.4(6) ? F1A C1 C55 . . 113.4(6) ? F2 C1 C55 . . 110.3(4) ? F3A C1 C55 . . 107.7(4) ? C55 C56 C51 . . 120.46(13) ? C55 C56 H56 . . 119.8 ? C51 C56 H56 . . 119.8 ? 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 Cl1 C52 . 1.738(2) ? S1 C5 . 1.718(2) ? S1 C2 . 1.721(2) ? O1 C21 . 1.224(2) ? C2 C3 . 1.382(2) ? C2 C21 . 1.472(2) ? C21 C22 . 1.503(2) ? C22 H22A . 0.9800 ? C22 H22B . 0.9800 ? C22 H22C . 0.9800 ? C3 C4 . 1.413(2) ? C3 H3 . 0.9500 ? C4 C5 . 1.378(2) ? C4 H4 . 0.9500 ? C5 C51 . 1.480(2) ? C51 C52 . 1.399(2) ? C51 C56 . 1.401(2) ? C52 C53 . 1.398(2) ? C53 C54 . 1.382(2) ? C53 H53 . 0.9500 ? C54 C55 . 1.393(2) ? C54 H54 . 0.9500 ? C55 C56 . 1.389(2) ? C55 C1 . 1.501(2) ? C1 F2A . 1.272(8) ? C1 F3 . 1.282(8) ? C1 F1 . 1.309(10) ? C1 F1A . 1.317(11) ? C1 F2 . 1.377(7) ? C1 F3A . 1.389(8) ? C56 H56 . 0.9500 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C22 H22C F1A 3_667 0.98 2.55 3.520(13) 168 C22 H22B O1 2_647 0.98 2.62 3.526(2) 154 C22 H22A O1 4_565 0.98 2.67 3.562(3) 152 C56 H56 O1 3_667 0.95 2.78 3.697(2) 162 _cod_database_fobs_code 2229358