#------------------------------------------------------------------------------ #$Date: 2025-02-13 04:12:46 +0200 (Thu, 13 Feb 2025) $ #$Revision: 297716 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573892.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1573892 loop_ _publ_author_name 'Yu, Yongjiang' 'Chen, Wang' 'Hu, Rongrong' 'Tang, Ben Zhong' _publ_section_title ; Base-free Multicomponent Polymerization of Elemental Sulfur, Difluoromethylene Phosphobetaine and Amines Toward Electron-Deficient Aromatic Polythioureas ; _journal_name_full 'Polymer Chemistry' _journal_paper_doi 10.1039/D4PY01387E _journal_year 2024 _chemical_formula_moiety 'C15 H16 N2 S' _chemical_formula_sum 'C15 H16 N2 S' _chemical_formula_weight 256.36 _space_group_crystal_system orthorhombic _space_group_IT_number 60 _space_group_name_Hall '-P 2n 2ab' _space_group_name_H-M_alt 'P b c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-07-05 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2024-12-03 deposited with the CCDC. 2025-02-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.6219(2) _cell_length_b 13.9013(2) _cell_length_c 8.4102(2) _cell_measurement_reflns_used 3310 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 73.8120 _cell_measurement_theta_min 4.9870 _cell_volume 1358.75(4) _computing_cell_refinement 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 12.00 37.00 0.50 0.50 -- -1.00 2.00 -67.00 50 2 \w -57.00 -32.00 0.50 0.50 -- 5.00 -2.00 127.00 50 3 \w -81.00 -55.00 0.50 0.50 -- -100.10 2.00 -67.00 52 4 \w -162.00-137.00 0.50 0.50 -- -100.10 -2.00 127.00 50 5 \w -16.00 9.00 0.50 0.50 -- -1.00 -72.00 60.00 50 6 \w -73.00 -44.00 0.50 0.50 -- -1.00 -72.00 60.00 58 7 \w -58.00 12.00 0.50 0.50 -- 1.00 -57.00 -30.00 140 8 \w -85.00 -60.00 0.50 0.50 -- 1.00 -57.00 -30.00 50 9 \w -188.00-141.00 0.50 0.50 -- -100.10 -19.00 -30.00 94 10 \w -132.00 -92.00 0.50 0.50 -- -100.10 -19.00 -30.00 80 11 \w -98.00 -58.00 0.50 0.50 -- -100.10 72.00-180.00 80 12 \w -105.00 -12.00 0.50 0.50 -- -100.10 72.00 90.00 186 13 \w -114.00 -33.00 0.50 0.50 -- -100.10 19.00 150.00 162 14 \w -112.00 -87.00 0.50 0.50 -- -100.10 72.00 150.00 50 15 \w -114.00 -49.00 0.50 0.50 -- -100.10 72.00 30.00 130 ; _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX2 area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0292684000 _diffrn_orient_matrix_UB_12 -0.1080270000 _diffrn_orient_matrix_UB_13 0.0051924000 _diffrn_orient_matrix_UB_21 0.1291553000 _diffrn_orient_matrix_UB_22 -0.0244485000 _diffrn_orient_matrix_UB_23 0.0021824000 _diffrn_orient_matrix_UB_31 -0.0005590000 _diffrn_orient_matrix_UB_32 0.0035099000 _diffrn_orient_matrix_UB_33 0.1832774000 _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 4973 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.966 _diffrn_reflns_theta_min 4.960 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 1.965 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.82167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.253 _exptl_crystal_description needle _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.223 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 84 _refine_ls_number_reflns 1331 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0340 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.5922P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.0937 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1268 _reflns_number_total 1331 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4py01387e2.cif _cod_data_source_block 1 _cod_database_code 1573892 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.981 _shelx_estimated_absorpt_t_min 0.962 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C3(H3), C4(H4), C6(H6), C7(H7) 2.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL 1_a.res in Pbcn 1.res created by SHELXL-2018/3 at 21:20:38 on 05-Jul-2023 REM Old TITL 1 in Pbcn REM SHELXT solution in Pbcn: R1 0.114, Rweak 0.026, Alpha 0.024 REM 0.709 for 220 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N2 Cl CELL 1.54184 11.6219 13.9013 8.4102 90 90 90 ZERR 4 0.0002 0.0002 0.0002 0 0 0 LATT 1 SYMM 0.5-X,0.5-Y,0.5+Z SYMM -X,+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N S UNIT 60 64 8 4 L.S. 20 PLAN 1 SIZE 0.01 0.01 0.02 TEMP 123.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.052100 0.592200 FVAR 0.73092 S1 4 0.500000 0.459213 0.250000 10.50000 0.02877 0.01558 = 0.01846 0.00000 0.00057 0.00000 N1 3 0.487966 0.630196 0.387142 11.00000 0.03150 0.01770 = 0.01791 0.00092 -0.00106 0.00295 AFIX 43 H1 2 0.512787 0.602534 0.471932 11.00000 -1.20000 AFIX 0 C1 1 0.283231 1.001777 0.478011 11.00000 0.03469 0.02745 = 0.05007 -0.01017 -0.00100 0.00755 AFIX 137 H1A 2 0.275710 1.033549 0.377197 11.00000 -1.50000 H1B 2 0.331314 1.039517 0.546738 11.00000 -1.50000 H1C 2 0.208607 0.994489 0.525448 11.00000 -1.50000 AFIX 0 C2 1 0.336787 0.903945 0.453878 11.00000 0.02656 0.02201 = 0.03009 -0.00312 0.00369 0.00248 C3 1 0.431033 0.874577 0.542521 11.00000 0.03583 0.02753 = 0.03052 -0.01155 -0.00591 0.00424 AFIX 43 H3 2 0.460877 0.915737 0.619323 11.00000 -1.20000 AFIX 0 C4 1 0.482193 0.785027 0.519551 11.00000 0.03250 0.02756 = 0.02578 -0.00503 -0.00651 0.00572 AFIX 43 H4 2 0.545485 0.766827 0.580159 11.00000 -1.20000 AFIX 0 C5 1 0.437953 0.723402 0.405700 11.00000 0.02611 0.01729 = 0.01846 0.00041 0.00321 0.00083 C6 1 0.342293 0.750599 0.317064 11.00000 0.02639 0.02234 = 0.02533 -0.00332 -0.00176 -0.00199 AFIX 43 H6 2 0.311611 0.708884 0.241726 11.00000 -1.20000 AFIX 0 C7 1 0.292952 0.840023 0.341467 11.00000 0.02349 0.02600 = 0.02959 0.00016 -0.00150 0.00231 AFIX 43 H7 2 0.229161 0.857841 0.281551 11.00000 -1.20000 AFIX 0 C8 1 0.500000 0.581522 0.250000 10.50000 0.02017 0.01862 = 0.01893 0.00000 -0.00122 0.00000 HKLF 4 REM 1_a.res in Pbcn REM wR2 = 0.0937, GooF = S = 1.058, Restrained GooF = 1.058 for all data REM R1 = 0.0340 for 1268 Fo > 4sig(Fo) and 0.0352 for all 1331 data REM 84 parameters refined using 0 restraints END WGHT 0.0521 0.5922 REM Highest difference peak 0.223, deepest hole -0.325, 1-sigma level 0.050 Q1 1 0.4655 0.5849 0.4743 11.00000 0.05 0.22 ; _shelx_res_checksum 14149 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.262 _oxdiff_exptl_absorpt_empirical_full_min 0.756 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' loop_ _atom_site_label _atom_site_type_symbol _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.500000 0.45921(3) 0.250000 0.02094(17) Uani 1 2 d S T P . . N1 N 0.48797(9) 0.63020(8) 0.38714(14) 0.0224(3) Uani 1 1 d . . . . . H1 H 0.512787 0.602534 0.471932 0.027 Uiso 1 1 calc R U . . . C1 C 0.28323(14) 1.00178(10) 0.4780(2) 0.0374(4) Uani 1 1 d . . . . . H1A H 0.275710 1.033549 0.377197 0.056 Uiso 1 1 calc R U . . . H1B H 0.331314 1.039517 0.546738 0.056 Uiso 1 1 calc R U . . . H1C H 0.208607 0.994489 0.525448 0.056 Uiso 1 1 calc R U . . . C2 C 0.33679(11) 0.90394(9) 0.45388(17) 0.0262(3) Uani 1 1 d . . . . . C3 C 0.43103(13) 0.87458(10) 0.54252(17) 0.0313(3) Uani 1 1 d . . . . . H3 H 0.460877 0.915737 0.619323 0.038 Uiso 1 1 calc R U . . . C4 C 0.48219(12) 0.78503(10) 0.51955(18) 0.0286(3) Uani 1 1 d . . . . . H4 H 0.545485 0.766827 0.580159 0.034 Uiso 1 1 calc R U . . . C5 C 0.43795(11) 0.72340(8) 0.40570(15) 0.0206(3) Uani 1 1 d . . . . . C6 C 0.34229(11) 0.75060(9) 0.31706(16) 0.0247(3) Uani 1 1 d . . . . . H6 H 0.311611 0.708884 0.241726 0.030 Uiso 1 1 calc R U . . . C7 C 0.29295(11) 0.84002(9) 0.34147(17) 0.0264(3) Uani 1 1 d . . . . . H7 H 0.229161 0.857841 0.281551 0.032 Uiso 1 1 calc R U . . . C8 C 0.500000 0.58152(13) 0.250000 0.0192(4) Uani 1 2 d S T P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0288(3) 0.0156(2) 0.0185(3) 0.000 0.00057(15) 0.000 N1 0.0315(6) 0.0177(5) 0.0179(6) 0.0009(4) -0.0011(4) 0.0029(4) C1 0.0347(8) 0.0274(7) 0.0501(10) -0.0102(7) -0.0010(7) 0.0075(6) C2 0.0266(7) 0.0220(7) 0.0301(7) -0.0031(5) 0.0037(5) 0.0025(5) C3 0.0358(8) 0.0275(7) 0.0305(8) -0.0116(6) -0.0059(6) 0.0042(6) C4 0.0325(7) 0.0276(7) 0.0258(7) -0.0050(6) -0.0065(5) 0.0057(5) C5 0.0261(6) 0.0173(6) 0.0185(6) 0.0004(5) 0.0032(5) 0.0008(5) C6 0.0264(7) 0.0223(6) 0.0253(7) -0.0033(5) -0.0018(5) -0.0020(5) C7 0.0235(6) 0.0260(7) 0.0296(7) 0.0002(5) -0.0015(5) 0.0023(5) C8 0.0202(8) 0.0186(9) 0.0189(9) 0.000 -0.0012(6) 0.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 H1 116.8 . . ? C8 N1 H1 116.8 . . ? C8 N1 C5 126.33(11) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? C3 C2 C1 121.25(13) . . ? C3 C2 C7 117.76(12) . . ? C7 C2 C1 120.99(13) . . ? C2 C3 H3 119.1 . . ? C2 C3 C4 121.72(13) . . ? C4 C3 H3 119.1 . . ? C3 C4 H4 120.3 . . ? C5 C4 C3 119.38(13) . . ? C5 C4 H4 120.3 . . ? C4 C5 N1 119.07(12) . . ? C4 C5 C6 119.97(12) . . ? C6 C5 N1 120.87(11) . . ? C5 C6 H6 120.1 . . ? C7 C6 C5 119.72(12) . . ? C7 C6 H6 120.1 . . ? C2 C7 H7 119.3 . . ? C6 C7 C2 121.44(12) . . ? C6 C7 H7 119.3 . . ? N1 C8 S1 120.22(8) 3_655 . ? N1 C8 S1 120.22(8) . . ? N1 C8 N1 119.57(16) . 3_655 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C8 1.7003(18) . ? N1 H1 0.8600 . ? N1 C5 1.4286(15) . ? N1 C8 1.3445(14) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 C2 1.5094(18) . ? C2 C3 1.386(2) . ? C2 C7 1.3939(19) . ? C3 H3 0.9300 . ? C3 C4 1.3930(19) . ? C4 H4 0.9300 . ? C4 C5 1.3839(18) . ? C5 C6 1.3909(18) . ? C6 H6 0.9300 . ? C6 C7 1.3843(18) . ? C7 H7 0.9300 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C5 C6 C7 177.65(12) . . . . ? C1 C2 C3 C4 -179.02(14) . . . . ? C1 C2 C7 C6 179.20(13) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C2 C7 C6 -0.8(2) . . . . ? C3 C4 C5 N1 -177.53(12) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 C7 1.1(2) . . . . ? C5 N1 C8 S1 -150.99(9) . . . . ? C5 N1 C8 N1 29.02(9) . . . 3_655 ? C5 C6 C7 C2 -0.2(2) . . . . ? C7 C2 C3 C4 1.0(2) . . . . ? C8 N1 C5 C4 -145.26(12) . . . . ? C8 N1 C5 C6 38.14(18) . . . . ?