#------------------------------------------------------------------------------ #$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012435.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_2012435 loop_ _publ_author_name 'Zi\,eba, Andrzej' 'Ma\'slankiewicz, Andrzej' 'Suwi\'nska, Kinga' _publ_section_title ; Azinyl Sulfides. LXVII. 1-Methylpyridine-4(1H)-thione ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o32 _journal_page_last o33 _journal_paper_doi 10.1107/S0108270101018029 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C6 H7 N1 S1' _chemical_formula_sum 'C6 H7 N S' _chemical_formula_weight 125.19 _chemical_name_systematic 1-Methyl-4(1H)-pyridinethione _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 89.840(10) _cell_angle_beta 84.030(10) _cell_angle_gamma 87.980(10) _cell_formula_units_Z 4 _cell_length_a 7.5440(10) _cell_length_b 9.0850(10) _cell_length_c 9.3020(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 19 _cell_measurement_theta_min 7 _cell_volume 633.68(13) _computing_cell_refinement 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'SDP (B. A. Frenz & Associates Inc., 1985)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .972 _diffrn_measured_fraction_theta_max .972 _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .022 _diffrn_reflns_av_sigmaI/netI .027 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2861 _diffrn_reflns_theta_full 78.18 _diffrn_reflns_theta_max 78.2 _diffrn_reflns_theta_min 4.8 _diffrn_standards_decay_% <1 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.590 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 264 _exptl_crystal_size_max .32 _exptl_crystal_size_mid .28 _exptl_crystal_size_min .26 _refine_diff_density_max .47 _refine_diff_density_min -.37 _refine_ls_extinction_coef .012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 148 _refine_ls_number_reflns 2654 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all .0635 _refine_ls_R_factor_gt .0459 _refine_ls_shift/su_max .018 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0893P)^2^+0.0559P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1258 _refine_ls_wR_factor_ref .1349 _reflns_number_gt 2012 _reflns_number_total 2654 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gg1079.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times). '_geom_angle_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (19 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 633.70(10) _cod_original_sg_symbol_H-M P-1 _cod_original_formula_sum 'C6 H7 N1 S1' _cod_database_code 2012435 _cod_database_fobs_code 2012435 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1A -.2188(2) .64031(19) .38365(18) .0449(4) Uani d . 1 . . N C2A -.0653(3) .6837(2) .4314(2) .0474(5) Uani d . 1 . . C H2A -.0708 .7490 .5087 .057 Uiso calc R 1 . . H C3A .0951(3) .6346(2) .3697(2) .0471(4) Uani d . 1 . . C H3A .1974 .6665 .4061 .057 Uiso calc R 1 . . H C4A .1131(3) .5359(2) .2512(2) .0429(4) Uani d . 1 . . C C5A -.0512(3) .4955(2) .2038(2) .0522(5) Uani d . 1 . . C H5A -.0503 .4318 .1256 .063 Uiso calc R 1 . . H C6A -.2091(3) .5474(2) .2697(3) .0532(5) Uani d . 1 . . C H6A -.3141 .5183 .2356 .064 Uiso calc R 1 . . H S41A .31282(8) .47185(6) .17014(7) .0587(2) Uani d . 1 . . S C11A -.3913(3) .6968(3) .4530(3) .0637(6) Uani d . 1 . . C H11A -.4856 .6602 .4028 .095 Uiso calc R 1 . . H H11B -.3951 .8025 .4498 .095 Uiso calc R 1 . . H H11C -.4062 .6648 .5519 .095 Uiso calc R 1 . . H N1B -.7288(2) .9911(2) 1.10807(17) .0470(4) Uani d . 1 . . N C2B -.6816(3) .8587(2) 1.0474(2) .0512(5) Uani d . 1 . . C H2B -.6389 .7839 1.1044 .061 Uiso calc R 1 . . H C3B -.6946(3) .8321(2) .9061(2) .0512(5) Uani d . 1 . . C H3B -.6583 .7401 .8680 .061 Uiso calc R 1 . . H C4B -.7621(3) .9408(2) .8143(2) .0435(4) Uani d . 1 . . C C5B -.8102(3) 1.0766(2) .8837(2) .0494(5) Uani d . 1 . . C H5B -.8557 1.1531 .8304 .059 Uiso calc R 1 . . H C6B -.7923(3) 1.0991(2) 1.0248(2) .0505(5) Uani d . 1 . . C H6B -.8244 1.1908 1.0657 .061 Uiso calc R 1 . . H S41B -.78108(9) .91137(8) .63710(6) .0669(2) Uani d . 1 . . S C11B -.7161(4) 1.0181(4) 1.2623(2) .0708(7) Uani d . 1 . . C H11D -.8287 1.0005 1.3164 .106 Uiso calc R 1 . . H H11E -.6852 1.1184 1.2758 .106 Uiso calc R 1 . . H H11F -.6259 .9531 1.2956 .106 Uiso calc R 1 . . 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 N1A .0404(9) .0451(8) .0498(9) -.0043(7) -.0076(7) -.0022(7) C2A .0496(11) .0475(10) .0469(10) -.0056(8) -.0125(8) -.0079(8) C3A .0440(10) .0464(10) .0534(10) -.0059(8) -.0149(8) -.0066(8) C4A .0429(10) .0363(8) .0510(10) -.0043(7) -.0107(8) .0003(7) C5A .0494(12) .0508(10) .0586(12) -.0065(9) -.0138(9) -.0164(9) C6A .0447(11) .0547(11) .0631(12) -.0091(9) -.0161(9) -.0116(9) S41A .0464(3) .0529(3) .0766(4) .0024(2) -.0067(2) -.0151(2) C11A .0464(12) .0706(15) .0726(15) .0004(11) .0000(10) -.0113(12) N1B .0467(9) .0561(10) .0389(8) -.0082(7) -.0058(7) -.0029(7) C2B .0515(12) .0478(10) .0553(11) -.0024(9) -.0102(9) .0078(9) C3B .0542(12) .0382(9) .0609(12) .0005(8) -.0059(9) -.0084(8) C4B .0411(10) .0477(10) .0419(9) -.0083(8) -.0038(7) -.0060(7) C5B .0590(12) .0409(9) .0485(10) .0002(9) -.0074(9) .0022(8) C6B .0587(12) .0420(9) .0502(11) -.0028(9) -.0027(9) -.0090(8) S41B .0719(4) .0870(5) .0437(3) -.0132(3) -.0108(2) -.0170(3) C11B .0709(16) .102(2) .0407(11) -.0151(15) -.0086(10) -.0077(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .3331 .5567 '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 _geom_angle_publ_flag C6A N1A C2A 118.71(19) yes C6A N1A C11A 121.21(19) yes C2A N1A C11A 120.07(19) yes C3A C2A N1A 121.57(18) yes C3A C2A H2A 119.2 ? N1A C2A H2A 119.2 ? C2A C3A C4A 122.11(18) yes C2A C3A H3A 118.9 ? C4A C3A H3A 118.9 ? C3A C4A C5A 114.18(19) yes C3A C4A S41A 123.53(16) yes C5A C4A S41A 122.29(15) yes C6A C5A C4A 121.52(19) yes C6A C5A H5A 119.2 ? C4A C5A H5A 119.2 ? N1A C6A C5A 121.90(19) ? N1A C6A H6A 119.1 ? C5A C6A H6A 119.1 ? N1A C11A H11A 109.5 ? N1A C11A H11B 109.5 ? H11A C11A H11B 109.5 ? N1A C11A H11C 109.5 ? H11A C11A H11C 109.5 ? H11B C11A H11C 109.5 ? C2B N1B C6B 118.80(17) yes C2B N1B C11B 121.2(2) yes C6B N1B C11B 120.0(2) yes N1B C2B C3B 121.77(19) yes N1B C2B H2B 119.1 ? C3B C2B H2B 119.1 ? C2B C3B C4B 121.76(19) yes C2B C3B H3B 119.1 ? C4B C3B H3B 119.1 ? C5B C4B C3B 113.95(18) yes C5B C4B S41B 122.90(16) yes C3B C4B S41B 123.14(15) yes C6B C5B C4B 122.29(19) yes C6B C5B H5B 118.9 ? C4B C5B H5B 118.9 ? C5B C6B N1B 121.40(18) yes C5B C6B H6B 119.3 ? N1B C6B H6B 119.3 ? N1B C11B H11D 109.5 ? N1B C11B H11E 109.5 ? H11D C11B H11E 109.5 ? N1B C11B H11F 109.5 ? H11D C11B H11F 109.5 ? H11E C11B H11F 109.5 ? 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 N1A C6A . 1.351(3) yes N1A C2A . 1.354(3) yes N1A C11A . 1.468(3) yes C2A C3A . 1.346(3) yes C2A H2A . .9300 ? C3A C4A . 1.415(3) yes C3A H3A . .9300 ? C4A C5A . 1.418(3) yes C4A S41A . 1.697(2) yes C5A C6A . 1.352(3) yes C5A H5A . .9300 ? C6A H6A . .9300 ? C11A H11A . .9600 ? C11A H11B . .9600 ? C11A H11C . .9600 ? N1B C2B . 1.351(3) yes N1B C6B . 1.353(3) yes N1B C11B . 1.470(3) yes C2B C3B . 1.351(3) yes C2B H2B . .9300 ? C3B C4B . 1.419(3) yes C3B H3B . .9300 ? C4B C5B . 1.412(3) yes C4B S41B . 1.6922(19) yes C5B C6B . 1.350(3) yes C5B H5B . .9300 ? C6B H6B . .9300 ? C11B H11D . .9600 ? C11B H11E . .9600 ? C11B H11F . .9600 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C6A N1A C2A C3A -1.1(3) C11A N1A C2A C3A -179.6(2) N1A C2A C3A C4A .4(3) C2A C3A C4A C5A .5(3) C2A C3A C4A S41A 179.83(16) C3A C4A C5A C6A -.7(3) S41A C4A C5A C6A 179.92(18) C2A N1A C6A C5A .9(3) C11A N1A C6A C5A 179.4(2) C4A C5A C6A N1A .1(4) C6B N1B C2B C3B .6(3) C11B N1B C2B C3B 179.3(2) N1B C2B C3B C4B -1.3(4) C2B C3B C4B C5B .9(3) C2B C3B C4B S41B -179.77(18) C3B C4B C5B C6B .1(3) S41B C4B C5B C6B -179.19(18) C4B C5B C6B N1B -.8(4) C2B N1B C6B C5B .5(3) C11B N1B C6B C5B -178.2(2)