#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005136.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_2005136 loop_ _publ_author_name 'Billing, D. G.' 'Boeyens, J. C. A.' 'Lai, L.-L.' 'Reid, D. H.' _publ_section_title ; 5-Ethylamino-3-p-tolyl-1\l^4^,2,4-thiaselenazol-1-ylium Bromide: a New Heteroaromatic System ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1718 _journal_page_last 1719 _journal_paper_doi 10.1107/S0108270195017252 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C11 H13 Br N2 S Se' _chemical_formula_weight 364.16 _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_type_scat_source IntTabC _cell_angle_alpha 90 _cell_angle_beta 99.42(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.237(2) _cell_length_b 10.434(1) _cell_length_c 17.450(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 123 _cell_measurement_theta_max 15 _cell_measurement_theta_min 8 _cell_volume 1299.9(4) _diffrn_measurement_device CAD4 _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.03 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3911 _diffrn_reflns_theta_max 30 _diffrn_standards_decay_% random _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 6.033 _exptl_absorpt_correction_T_max 0.530 _exptl_absorpt_correction_T_min 0.370 _exptl_absorpt_correction_type analytical _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.861 _exptl_crystal_description needle _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _refine_diff_density_max 1.07 _refine_diff_density_min -0.99 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 0.983 _refine_ls_hydrogen_treatment 'H-atom coordinates refined' _refine_ls_number_parameters 148 _refine_ls_number_reflns 3776 _refine_ls_R_factor_obs 0.0355 _refine_ls_shift/esd_max -0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(F~o~^2^)+(0.0617P)^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.0969 _reflns_number_observed 2840 _reflns_number_total 3776 _reflns_observed_criterion F>4\s(F) _cod_data_source_file ka1156.cif _cod_data_source_block ka1156a _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value ' 1/[\s^2^(F~o~^2^)+(0.0617P)^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F~o~^2^)+(0.0617P)^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2005136 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,1/2+z -x,-y,-z 1/2-x,1/2+y,1/2-z 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 Br .0220(10) .0110(10) .0160(10) .0040(10) .0060(10) .0020(10) Se .0160(10) .0120(10) .0130(10) .0020(10) .0020(10) .0000(10) S .0130(10) .0100(10) .0120(10) .0010(10) .0020(10) .0000(10) N(1) .0110(10) .0070(10) .0150(10) .0010(10) 0.0010(10) .0000(10) N(2) .0180(10) .0100(10) .0120(10) .0010(10) .0010(10) .0000(10) C(1) .0090(10) .0090(10) .0160(10) -.0010(10) .0010(10) -.0020(10) C(2) .0090(10) .0110(10) .0140(10) -.0020(10) .0020(10) -.0010(10) C(3) .0110(10) .0100(10) .0140(10) -.0010(10) .0010(10) .0010(10) C(4) .016(2) .014(2) .0110(10) .0010(10) .0030(10) -.0010(10) C(5) .0160(10) .0100(10) .0150(10) .0020(10) .0030(10) -.0020(10) C(6) .0120(10) .0080(10) .0190(10) -.0010(10) .0020(10) .0010(10) C(7) .0150(10) .012(2) .0130(10) .0020(10) .0000(10) .0010(10) C(8) .0130(10) .0120(10) .0120(10) .0020(10) .0000(10) -.0020(10) C(9) .019(2) .011(2) .022(2) .0020(10) .0020(10) .0030(10) C(10) .029(2) .014(2) .0140(10) .0010(10) .0040(10) -.0020(10) C(11) .002(2) .021(2) .0110(10) .0010(10) .0020(10) .0020(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv Br .5532(1) .4582(1) .6666(1) .016(1) Se .3300(1) .8077(1) .4139(1) .014(1) S .4137(1) .6724(1) .5091(1) .011(1) N(1) .3164(4) .9039(3) .5614(2) .011(1) N(2) .4128(4) .7498(3) .6538(2) .013(1) C(2) .2821(4) .9320(3) .4869(2) .011(1) C(1) .3786(4) .7845(3) .5811(2) .012(1) C(3) .2093(4) 1.0567(3) .4604(2) .012(1) C(4) .1695(5) 1.1477(3) .5141(2) .014(1) C(5) .1010(4) 1.2668(3) .4899(2) .014(1) C(6) .0690(4) 1.3000(3) .4107(2) .013(1) C(7) .1080(4) 1.2097(3) .3573(2) .013(1) C(8) .1756(4) 1.0883(3) .3809(2) .013(1) C(9) -.0028(5) 1.4307(3) .3855(2) .018(1) C(10) .3917(5) .8318(3) .7200(2) .019(1) C(11) .3486(5) .7515(4) .7865(2) .018(1) H(2) .4517(4) .6707(3) .6640(2) .025(3) H(4) .1898(5) 1.1272(3) .5679(2) .025(3) H(5) .0749(4) 1.3275(3) .5273(2) .025(3) H(7) .0884(4) 1.2309(3) .3036(2) .025(3) H(8) .1988(4) 1.0270(3) .3434(2) .025(3) H(9A) .0924(15) 1.4951(4) .4045(13) .025(3) H(9B) -.1172(20) 1.4484(10) .4069(12) .025(3) H(9C) -.0305(34) 1.4342(8) .3287(2) .025(3) H(10A) .2890(5) .8939(3) .7043(2) .025(3) H(10B) .5087(5) .8806(3) .7365(2) .025(3) H(11A) .3339(36) .8073(4) .8303(6) .025(3) H(11B) .4516(17) .6912(17) .8025(10) .025(3) H(11C) .2324(20) .7037(19) .7700(5) .025(3) 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 C(2) Se S 89.36(10) yes C(1) S Se 93.36(11) yes C(2) N(1) C(1) 117.3(3) yes C(1) N(2) C(10) 125.2(3) yes N(2) C(1) N(1) 120.4(3) yes N(2) C(1) S 118.8(2) yes N(1) C(1) S 120.7(2) yes N(1) C(2) C(3) 121.0(3) yes N(1) C(2) Se 119.2(2) yes C(3) C(2) Se 119.8(2) yes C(4) C(3) C(8) 118.7(3) yes C(4) C(3) C(2) 120.0(3) yes C(8) C(3) C(2) 121.3(3) yes C(5) C(4) C(3) 120.7(3) yes C(4) C(5) C(6) 121.0(3) yes C(7) C(6) C(5) 118.3(3) yes C(7) C(6) C(9) 121.3(3) yes C(5) C(6) C(9) 120.3(3) yes C(6) C(7) C(8) 121.2(3) yes C(7) C(8) C(3) 119.9(3) yes N(2) C(10) C(11) 110.1(3) yes C(1) N(2) H(2) 117.4(2) no C(10) N(2) H(2) 117.4(2) no C(5) C(4) H(4) 119.7(2) no C(3) C(4) H(4) 119.7(2) no C(4) C(5) H(5) 119.5(2) no C(6) C(5) H(5) 119.5(2) no C(6) C(7) H(7) 119.4(2) no C(8) C(7) H(7) 119.4(2) no C(7) C(8) H(8) 120.0(2) no C(3) C(8) H(8) 120.0(2) no C(6) C(9) H(9A) 109.5(2) no C(6) C(9) H(9B) 109.5(2) no H(9A) C(9) H(9B) 109.5 no C(6) C(9) H(9C) 109.5(2) no H(9A) C(9) H(9C) 109.5 no H(9B) C(9) H(9C) 109.5 no N(2) C(10) H(10A) 109.6(2) no C(11) C(10) H(10A) 109.6(2) no N(2) C(10) H(10B) 109.6(2) no C(11) C(10) H(10B) 109.6(2) no H(10A) C(10) H(10B) 108.2 no C(10) C(11) H(11A) 109.5(2) no C(10) C(11) H(11B) 109.5(2) no H(11A) C(11) H(11B) 109.5 no C(10) C(11) H(11C) 109.5(2) no H(11A) C(11) H(11C) 109.5 no H(11B) C(11) H(11C) 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Se C(2) 1.890(3) yes Se S 2.189(2) yes S C(1) 1.765(3) yes N(1) C(2) 1.315(4) yes N(1) C(1) 1.350(4) yes N(2) C(1) 1.304(4) yes N(2) C(10) 1.465(4) yes C(2) C(3) 1.451(4) yes C(3) C(4) 1.396(4) yes C(3) C(8) 1.408(4) yes C(4) C(5) 1.379(4) yes C(5) C(6) 1.407(4) yes C(6) C(7) 1.386(4) yes C(6) C(9) 1.500(4) yes C(7) C(8) 1.396(4) yes C(10) C(11) 1.505(4) yes N(2) H(2) 0.88 no C(4) H(4) 0.95 no C(5) H(5) 0.95 no C(7) H(7) 0.95 no C(8) H(8) 0.95 no C(9) H(9A) 0.98 no C(9) H(9B) 0.98 no C(9) H(9C) 0.98 no C(10) H(10A) 0.99 no C(10) H(10B) 0.99 no C(11) H(11A) 0.98 no C(11) H(11B) 0.98 no C(11) H(11C) 0.98 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139055038