#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:19:36 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257998 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240560.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_7240560 loop_ _publ_author_name 'Lu, Shi-Chao' 'Wu, Botao' 'Zhang, Shi-Peng' 'Gong, Ya-Ling' 'Xu, Shu' _publ_section_title ; K2S2O8-mediated radical cyclisation of 2-alkynylthioanisoles or -selenoanisoles: a green and regioselective route to 3-nitrobenzothiophenes and benzoselenophenes ; _journal_issue 32 _journal_name_full 'RSC Advances' _journal_page_first 19083 _journal_page_last 19087 _journal_paper_doi 10.1039/D0RA03894F _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C14 H9 N O2 S' _chemical_formula_sum 'C14 H9 N O2 S' _chemical_formula_weight 255.28 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-01-18 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-07 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.5030(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.2070(2) _cell_length_b 17.4113(6) _cell_length_c 10.8693(4) _cell_measurement_reflns_used 9722 _cell_measurement_temperature 178(2) _cell_measurement_theta_max 55.05 _cell_measurement_theta_min 4.215 _cell_volume 1158.55(7) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 178.27 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0600 _diffrn_reflns_av_unetI/netI 0.0444 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10969 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 55.022 _diffrn_reflns_theta_min 4.213 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.590 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.5225 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1821 before and 0.0937 after correction. The Ratio of minimum to maximum transmission is 0.6959. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.464 _exptl_crystal_description block _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.491 _refine_diff_density_min -0.729 _refine_diff_density_rms 0.090 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2175 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0543 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1009P)^2^+0.3463P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1424 _refine_ls_wR_factor_ref 0.1441 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2060 _reflns_number_total 2175 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03894f2.cif _cod_data_source_block 1901162580_0m _cod_depositor_comments 'Adding full bibliography for 7240560.cif.' _cod_database_code 7240560 _shelx_shelxl_version_number 2016/6 _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 0.925 _shelx_estimated_absorpt_t_min 0.857 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14) ; _shelx_res_file ; TITL 1901162580_0m_a.res in P2(1)/c 1901162580_0m.res created by SHELXL-2016/6 at 17:09:58 on 18-Jan-2019 REM Old TITL 1901162580_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.121, Rweak 0.005, Alpha 0.034, Orientation as input REM Formula found by SHELXT: C15 O2 Cl CELL 1.34139 6.207 17.4113 10.8693 90 99.503 90 ZERR 4 0.0002 0.0006 0.0004 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S DISP C 0.0148 0.007 57.7477 DISP H -0 0 0.6481 DISP O 0.0412 0.025 193.9543 UNIT 56 36 4 8 4 L.S. 4 PLAN 20 SIZE 0.05 0.08 0.1 TEMP -94.88 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.100900 0.346300 FVAR 1.31049 S1 5 0.152284 0.484370 0.674151 11.00000 0.02675 0.02518 = 0.03833 0.00154 -0.00170 -0.00406 O1 4 0.850881 0.602457 0.823330 11.00000 0.02965 0.04186 = 0.05310 0.00556 -0.00423 -0.00937 O2 4 0.618224 0.680713 0.722420 11.00000 0.04649 0.02446 = 0.05834 0.00457 -0.00394 -0.00874 N1 3 0.668406 0.616905 0.764567 11.00000 0.03007 0.02697 = 0.03175 -0.00185 0.00440 -0.00559 C1 1 0.336130 0.443476 0.793851 11.00000 0.02793 0.02393 = 0.03223 -0.00330 0.00187 -0.00046 C2 1 0.307263 0.374748 0.855633 11.00000 0.03718 0.02675 = 0.03874 -0.00060 0.00416 -0.00625 AFIX 43 H2 2 0.174870 0.346557 0.836849 11.00000 -1.20000 AFIX 0 C3 1 0.476330 0.349015 0.944603 11.00000 0.04731 0.02552 = 0.03482 0.00360 0.00572 -0.00200 AFIX 43 H3 2 0.461348 0.302192 0.987260 11.00000 -1.20000 AFIX 0 C4 1 0.669596 0.391357 0.972449 11.00000 0.03994 0.03205 = 0.03251 0.00106 -0.00092 0.00359 AFIX 43 H4 2 0.784877 0.372286 1.033220 11.00000 -1.20000 AFIX 0 C5 1 0.697108 0.459836 0.914193 11.00000 0.03111 0.02997 = 0.03324 -0.00195 -0.00025 -0.00188 AFIX 43 H5 2 0.828577 0.488255 0.935740 11.00000 -1.20000 AFIX 0 C6 1 0.528919 0.487335 0.822533 11.00000 0.02830 0.02252 = 0.02842 -0.00399 0.00504 -0.00131 C7 1 0.509697 0.555724 0.746671 11.00000 0.02611 0.02193 = 0.02965 -0.00356 0.00568 -0.00195 C8 1 0.320779 0.561530 0.661640 11.00000 0.02725 0.02167 = 0.03002 -0.00383 0.00623 0.00012 C9 1 0.255427 0.617248 0.559917 11.00000 0.02841 0.02092 = 0.02823 -0.00393 0.00097 -0.00095 C10 1 0.382163 0.625388 0.466172 11.00000 0.03468 0.02957 = 0.03517 -0.00180 0.00678 0.00408 AFIX 43 H10 2 0.513043 0.596578 0.469823 11.00000 -1.20000 AFIX 0 C11 1 0.318296 0.675181 0.367931 11.00000 0.04940 0.03328 = 0.02977 -0.00050 0.00951 0.00004 AFIX 43 H11 2 0.405143 0.680348 0.304160 11.00000 -1.20000 AFIX 0 C12 1 0.127941 0.717617 0.362111 11.00000 0.05372 0.02534 = 0.03266 0.00124 -0.00586 0.00193 AFIX 43 H12 2 0.085203 0.752326 0.295086 11.00000 -1.20000 AFIX 0 C13 1 0.000643 0.709228 0.454174 11.00000 0.03556 0.02923 = 0.04558 -0.00192 -0.00251 0.00724 AFIX 43 H13 2 -0.130307 0.738062 0.449961 11.00000 -1.20000 AFIX 0 C14 1 0.062534 0.659088 0.552572 11.00000 0.02898 0.02617 = 0.03853 -0.00403 0.00546 0.00131 AFIX 43 H14 2 -0.026637 0.653236 0.615080 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1901162580_0m_a.res in P2(1)/c REM R1 = 0.0543 for 2060 Fo > 4sig(Fo) and 0.0558 for all 2175 data REM 163 parameters refined using 0 restraints END WGHT 0.1004 0.3761 REM Highest difference peak 0.491, deepest hole -0.729, 1-sigma level 0.090 Q1 1 0.1757 0.5362 0.6796 11.00000 0.05 0.49 Q2 1 0.0958 0.5280 0.7132 11.00000 0.05 0.49 Q3 1 0.5433 0.5184 0.7851 11.00000 0.05 0.41 Q4 1 0.8563 0.5523 0.8127 11.00000 0.05 0.38 Q5 1 0.1826 0.4334 0.6478 11.00000 0.05 0.32 Q6 1 0.3315 0.4138 0.8194 11.00000 0.05 0.31 Q7 1 0.0712 0.7025 0.5442 11.00000 0.05 0.29 Q8 1 0.2905 0.5899 0.5075 11.00000 0.05 0.28 Q9 1 0.3759 0.3015 0.9739 11.00000 0.05 0.28 Q10 1 0.2678 0.5782 0.6004 11.00000 0.05 0.27 Q11 1 0.9486 0.5427 0.7840 11.00000 0.05 0.27 Q12 1 0.2198 0.4879 0.7990 11.00000 0.05 0.26 Q13 1 0.6448 0.4305 0.9548 11.00000 0.05 0.25 Q14 1 0.1382 0.3717 0.6631 11.00000 0.05 0.24 Q15 1 0.2985 0.6235 0.3777 11.00000 0.05 0.23 Q16 1 0.4944 0.2927 0.9461 11.00000 0.05 0.23 Q17 1 0.4572 0.5692 0.4601 11.00000 0.05 0.23 Q18 1 0.3992 0.4726 0.8374 11.00000 0.05 0.23 Q19 1 0.6475 0.6386 0.6902 11.00000 0.05 0.22 Q20 1 -0.0423 0.8177 0.3302 11.00000 0.05 0.21 ; _shelx_res_checksum 92328 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0.15228(7) 0.48437(2) 0.67415(4) 0.0309(2) Uani 1 1 d . . . . . O1 O 0.8509(2) 0.60246(9) 0.82333(14) 0.0428(4) Uani 1 1 d . . . . . O2 O 0.6182(2) 0.68071(8) 0.72242(15) 0.0445(4) Uani 1 1 d . . . . . N1 N 0.6684(2) 0.61690(8) 0.76457(14) 0.0297(4) Uani 1 1 d . . . . . C1 C 0.3361(3) 0.44348(10) 0.79385(18) 0.0284(4) Uani 1 1 d . . . . . C2 C 0.3073(3) 0.37475(10) 0.85563(19) 0.0345(4) Uani 1 1 d . . . . . H2 H 0.174870 0.346557 0.836849 0.041 Uiso 1 1 calc R . . . . C3 C 0.4763(3) 0.34902(11) 0.94460(18) 0.0360(5) Uani 1 1 d . . . . . H3 H 0.461348 0.302192 0.987260 0.043 Uiso 1 1 calc R . . . . C4 C 0.6696(3) 0.39136(11) 0.97245(19) 0.0356(5) Uani 1 1 d . . . . . H4 H 0.784877 0.372286 1.033220 0.043 Uiso 1 1 calc R . . . . C5 C 0.6971(3) 0.45984(11) 0.91419(18) 0.0321(4) Uani 1 1 d . . . . . H5 H 0.828577 0.488255 0.935740 0.038 Uiso 1 1 calc R . . . . C6 C 0.5289(3) 0.48733(9) 0.82253(17) 0.0264(4) Uani 1 1 d . . . . . C7 C 0.5097(3) 0.55572(9) 0.74667(16) 0.0258(4) Uani 1 1 d . . . . . C8 C 0.3208(3) 0.56153(9) 0.66164(16) 0.0261(4) Uani 1 1 d . . . . . C9 C 0.2554(3) 0.61725(9) 0.55992(16) 0.0263(4) Uani 1 1 d . . . . . C10 C 0.3822(3) 0.62539(10) 0.46617(18) 0.0330(4) Uani 1 1 d . . . . . H10 H 0.513043 0.596578 0.469823 0.040 Uiso 1 1 calc R . . . . C11 C 0.3183(3) 0.67518(11) 0.36793(19) 0.0371(5) Uani 1 1 d . . . . . H11 H 0.405143 0.680348 0.304160 0.045 Uiso 1 1 calc R . . . . C12 C 0.1279(4) 0.71762(11) 0.36211(19) 0.0387(5) Uani 1 1 d . . . . . H12 H 0.085203 0.752326 0.295086 0.046 Uiso 1 1 calc R . . . . C13 C 0.0006(3) 0.70923(11) 0.4542(2) 0.0378(5) Uani 1 1 d . . . . . H13 H -0.130307 0.738062 0.449961 0.045 Uiso 1 1 calc R . . . . C14 C 0.0625(3) 0.65909(10) 0.55257(18) 0.0312(4) Uani 1 1 d . . . . . H14 H -0.026637 0.653236 0.615080 0.037 Uiso 1 1 calc R . . . . 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 0.0268(3) 0.0252(3) 0.0383(4) 0.00154(16) -0.0017(2) -0.00406(15) O1 0.0297(7) 0.0419(9) 0.0531(10) 0.0056(6) -0.0042(6) -0.0094(5) O2 0.0465(8) 0.0245(7) 0.0583(10) 0.0046(6) -0.0039(7) -0.0087(6) N1 0.0301(8) 0.0270(8) 0.0318(8) -0.0018(6) 0.0044(6) -0.0056(6) C1 0.0279(9) 0.0239(9) 0.0322(9) -0.0033(7) 0.0019(7) -0.0005(6) C2 0.0372(10) 0.0267(9) 0.0387(11) -0.0006(8) 0.0042(8) -0.0063(7) C3 0.0473(11) 0.0255(9) 0.0348(10) 0.0036(7) 0.0057(8) -0.0020(8) C4 0.0399(10) 0.0321(9) 0.0325(10) 0.0011(8) -0.0009(8) 0.0036(8) C5 0.0311(9) 0.0300(9) 0.0332(10) -0.0019(7) -0.0002(7) -0.0019(7) C6 0.0283(9) 0.0225(9) 0.0284(9) -0.0040(6) 0.0050(7) -0.0013(6) C7 0.0261(8) 0.0219(8) 0.0297(9) -0.0036(7) 0.0057(7) -0.0020(6) C8 0.0272(8) 0.0217(8) 0.0300(9) -0.0038(7) 0.0062(7) 0.0001(6) C9 0.0284(8) 0.0209(8) 0.0282(9) -0.0039(6) 0.0010(7) -0.0009(6) C10 0.0347(9) 0.0296(9) 0.0352(10) -0.0018(8) 0.0068(8) 0.0041(7) C11 0.0494(11) 0.0333(10) 0.0298(10) -0.0005(8) 0.0095(8) 0.0000(8) C12 0.0537(12) 0.0253(9) 0.0327(11) 0.0012(7) -0.0059(9) 0.0019(8) C13 0.0356(10) 0.0292(10) 0.0456(12) -0.0019(8) -0.0025(9) 0.0072(7) C14 0.0290(9) 0.0262(9) 0.0385(10) -0.0040(7) 0.0055(7) 0.0013(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0148 0.0070 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2925 0.4295 '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 C8 S1 C1 92.67(8) . . ? O1 N1 C7 117.94(15) . . ? O2 N1 O1 122.41(15) . . ? O2 N1 C7 119.65(15) . . ? C2 C1 S1 126.21(14) . . ? C2 C1 C6 121.91(17) . . ? C6 C1 S1 111.87(14) . . ? C1 C2 H2 120.9 . . ? C3 C2 C1 118.15(17) . . ? C3 C2 H2 120.9 . . ? C2 C3 H3 119.8 . . ? C2 C3 C4 120.46(18) . . ? C4 C3 H3 119.8 . . ? C3 C4 H4 119.2 . . ? C5 C4 C3 121.70(18) . . ? C5 C4 H4 119.2 . . ? C4 C5 H5 120.4 . . ? C4 C5 C6 119.27(17) . . ? C6 C5 H5 120.4 . . ? C1 C6 C7 109.49(16) . . ? C5 C6 C1 118.48(16) . . ? C5 C6 C7 132.03(17) . . ? C6 C7 N1 122.86(15) . . ? C8 C7 N1 121.69(15) . . ? C8 C7 C6 115.27(15) . . ? C7 C8 S1 110.62(13) . . ? C7 C8 C9 130.66(16) . . ? C9 C8 S1 118.46(13) . . ? C10 C9 C8 119.73(16) . . ? C14 C9 C8 120.93(17) . . ? C14 C9 C10 119.26(17) . . ? C9 C10 H10 119.9 . . ? C11 C10 C9 120.29(17) . . ? C11 C10 H10 119.9 . . ? C10 C11 H11 119.9 . . ? C10 C11 C12 120.22(19) . . ? C12 C11 H11 119.9 . . ? C11 C12 H12 120.1 . . ? C13 C12 C11 119.72(18) . . ? C13 C12 H12 120.1 . . ? C12 C13 H13 119.8 . . ? C12 C13 C14 120.48(18) . . ? C14 C13 H13 119.8 . . ? C9 C14 H14 120.0 . . ? C13 C14 C9 120.02(18) . . ? C13 C14 H14 120.0 . . ? 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 C1 1.7354(19) . ? S1 C8 1.7217(17) . ? O1 N1 1.231(2) . ? O2 N1 1.222(2) . ? N1 C7 1.442(2) . ? C1 C2 1.398(3) . ? C1 C6 1.410(2) . ? C2 H2 0.9500 . ? C2 C3 1.379(3) . ? C3 H3 0.9500 . ? C3 C4 1.398(3) . ? C4 H4 0.9500 . ? C4 C5 1.374(3) . ? C5 H5 0.9500 . ? C5 C6 1.403(3) . ? C6 C7 1.442(2) . ? C7 C8 1.372(2) . ? C8 C9 1.476(2) . ? C9 C10 1.393(3) . ? C9 C14 1.392(2) . ? C10 H10 0.9500 . ? C10 C11 1.382(3) . ? C11 H11 0.9500 . ? C11 C12 1.386(3) . ? C12 H12 0.9500 . ? C12 C13 1.381(3) . ? C13 H13 0.9500 . ? C13 C14 1.385(3) . ? C14 H14 0.9500 . ?