#------------------------------------------------------------------------------ #$Date: 2026-06-25 00:06:42 +0100 (Thu, 25 Jun 2026) $ #$Revision: 306637 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577426.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_1577426 loop_ _publ_author_name 'Tian, Peilin' 'Saraiva C\^amara, Viktor' 'Valentine, Margarita' 'Tinkler, Andrew P.' 'Crumpton, Agamemnon E.' 'Anderson, Edward A.' _publ_section_title ; Enantioselective Titanium-Catalyzed Cycloadditions of Thiophene-S,S-Dioxides with Indenes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC01387B _journal_year 2026 _chemical_formula_moiety 'C8 H6 Cl N O5 S' _chemical_formula_sum 'C8 H6 Cl N O5 S' _chemical_formula_weight 263.66 _chemical_melting_point ? _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary other _audit_creation_date 2025-06-02 _audit_creation_method 'CRYSTALS_ver_14_build_c42b451 ' _audit_update_record ; 2025-12-02 deposited with the CCDC. 2026-06-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.9999(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.97250(10) _cell_length_b 6.52180(10) _cell_length_c 14.02240(10) _cell_measurement_reflns_used 20079 _cell_measurement_temperature 100 _cell_measurement_theta_max 74.93 _cell_measurement_theta_min 4.86 _cell_volume 997.952(19) _computing_cell_refinement ; CrysAlisPro (Rigaku Oxford Diffraction, 2021) ; _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_data_reduction ; CrysAlisPro (Rigaku Oxford Diffraction, 2021) ; _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'focussing mirrors' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_unetI/netI 0.034 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 31025 _diffrn_reflns_theta_full 73.497 _diffrn_reflns_theta_max 75.771 _diffrn_reflns_theta_min 4.878 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.462 _exptl_absorpt_correction_T_max 0.62 _exptl_absorpt_correction_T_min 0.32 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro (Rigaku Oxford Diffraction, 2021) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.272 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.087 _refine_diff_density_max 0.69 _refine_diff_density_min -0.65 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 2038 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0341 _refine_ls_shift/su_max 0.0003660 _refine_ls_shift/su_mean 0.0000297 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.53P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0860 _refine_ls_wR_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.0860 _reflns_limit_h_max 13 _reflns_limit_h_min -13 _reflns_limit_k_max 8 _reflns_limit_k_min 0 _reflns_limit_l_max 17 _reflns_limit_l_min 0 _reflns_number_gt 1970 _reflns_number_total 2038 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 1.73 _oxford_diffrn_Wilson_scale 3.62 _oxford_refine_ls_scale 0.5308(12) _oxford_structure_analysis_title 7882 _iucr_refine_instructions_details ; # # Punched on 02/06/25 at 16:17:47 # #LIST 12 BLOCK SCALE X'S U'S RIDE C ( 12,X'S) H ( 122,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) END # # Punched on 02/06/25 at 16:17:47 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _cod_data_source_file d6sc01387b2.cif _cod_data_source_block 1a _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value 'not measured' was changed to '?' -- the value is undefined or not given. data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_sg_symbol_Hall '-P 2yn ' _cod_original_sg_symbol_H-M 'P 21/n ' _cod_database_code 1577426 _oxford_refine_reflns_threshold_expression I>-3.0\s(I) _refine_ls_r_factor_ref 0.0350 _reflns_number_all 2038 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,-y+1/2,z+1/2 -x+1/2,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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cl1 Cl 0.79785(5) 0.69166(8) 0.69508(3) 0.0290 1.0000 Uani . . . . . . C2 C 0.73039(19) 0.7348(3) 0.58237(14) 0.0222 1.0000 Uani . . . . . . S3 S 0.72366(5) 0.99231(7) 0.54000(3) 0.0231 1.0000 Uani . . . . . . O4 O 0.84401(15) 1.0662(3) 0.52871(11) 0.0339 1.0000 Uani . . . . . . O5 O 0.64835(15) 1.1112(2) 0.59733(10) 0.0299 1.0000 Uani . . . . . . C6 C 0.6451(2) 0.9170(3) 0.42756(14) 0.0232 1.0000 Uani . . . . . . C7 C 0.59921(19) 1.0826(3) 0.36219(13) 0.0212 1.0000 Uani . . . . . . O8 O 0.57697(15) 1.2500(2) 0.39509(10) 0.0272 1.0000 Uani . . . . . . N9 N 0.57536(16) 1.0501(2) 0.26427(11) 0.0206 1.0000 Uani . . . . . . C10 C 0.62896(19) 0.9043(3) 0.20896(14) 0.0237 1.0000 Uani . . . . . . O11 O 0.60961(15) 0.9590(2) 0.11633(10) 0.0289 1.0000 Uani . . . . . . C12 C 0.5296(2) 1.1365(3) 0.10457(14) 0.0262 1.0000 Uani . . . . . . C13 C 0.5279(2) 1.2246(3) 0.20504(14) 0.0246 1.0000 Uani . . . . . . O14 O 0.68396(15) 0.7522(2) 0.23564(10) 0.0302 1.0000 Uani . . . . . . C15 C 0.6261(2) 0.7141(3) 0.42893(14) 0.0238 1.0000 Uani . . . . . . C16 C 0.6746(2) 0.6091(3) 0.51815(14) 0.0242 1.0000 Uani . . . . . . H122 H 0.5618 1.2310 0.0605 0.0317 1.0000 Uiso R . . . . . H121 H 0.4501 1.0928 0.0783 0.0317 1.0000 Uiso R . . . . . H131 H 0.5822 1.3400 0.2153 0.0295 1.0000 Uiso R . . . . . H132 H 0.4466 1.2609 0.2181 0.0298 1.0000 Uiso R . . . . . H151 H 0.5844 0.6435 0.3780 0.0298 1.0000 Uiso R . . . . . H161 H 0.6641 0.4684 0.5272 0.0299 1.0000 Uiso 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 Cl1 0.0471(3) 0.0222(3) 0.0156(2) 0.00258(17) -0.00721(19) 0.0055(2) C2 0.0334(10) 0.0166(9) 0.0158(9) 0.0030(7) -0.0019(8) 0.0036(8) S3 0.0387(3) 0.0139(2) 0.0147(2) -0.00002(16) -0.00769(19) -0.00210(19) O4 0.0420(9) 0.0289(8) 0.0284(8) 0.0026(6) -0.0072(7) -0.0097(7) O5 0.0501(9) 0.0192(7) 0.0182(7) -0.0031(6) -0.0064(6) 0.0052(7) C6 0.0352(11) 0.0178(9) 0.0147(9) -0.0019(7) -0.0061(8) -0.0017(8) C7 0.0306(10) 0.0160(9) 0.0154(9) -0.0007(7) -0.0048(7) -0.0021(8) O8 0.0446(9) 0.0173(7) 0.0180(7) -0.0029(6) -0.0050(6) 0.0023(6) N9 0.0323(9) 0.0144(8) 0.0137(7) 0.0003(6) -0.0042(6) 0.0021(7) C10 0.0323(10) 0.0211(10) 0.0164(9) -0.0014(8) -0.0042(8) 0.0022(8) O11 0.0435(9) 0.0273(8) 0.0147(7) -0.0002(6) -0.0025(6) 0.0110(7) C12 0.0378(11) 0.0223(10) 0.0172(9) 0.0020(8) -0.0030(8) 0.0081(9) C13 0.0367(11) 0.0182(9) 0.0173(9) 0.0018(8) -0.0050(8) 0.0040(8) O14 0.0443(9) 0.0235(7) 0.0215(7) 0.0000(6) -0.0033(6) 0.0119(7) C15 0.0352(11) 0.0173(9) 0.0175(9) -0.0017(7) -0.0041(8) -0.0020(8) C16 0.0375(11) 0.0149(9) 0.0195(9) 0.0013(7) -0.0005(8) 0.0000(8) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 . C2 . S3 . 117.77(12) yes Cl1 . C2 . C16 . 131.17(16) yes S3 . C2 . C16 . 110.98(15) yes C2 . S3 . O4 . 110.39(10) yes C2 . S3 . O5 . 109.15(9) yes O4 . S3 . O5 . 118.11(10) yes C2 . S3 . C6 . 91.98(9) yes O4 . S3 . C6 . 111.18(10) yes O5 . S3 . C6 . 112.91(10) yes S3 . C6 . C7 . 116.80(14) yes S3 . C6 . C15 . 108.69(15) yes C7 . C6 . C15 . 133.65(19) yes C6 . C7 . O8 . 119.37(17) yes C6 . C7 . N9 . 121.46(17) yes O8 . C7 . N9 . 119.10(17) yes C7 . N9 . C10 . 127.40(17) yes C7 . N9 . C13 . 117.38(16) yes C10 . N9 . C13 . 110.97(15) yes N9 . C10 . O11 . 108.88(16) yes N9 . C10 . O14 . 128.12(18) yes O11 . C10 . O14 . 123.01(19) yes C10 . O11 . C12 . 110.76(15) yes O11 . C12 . C13 . 105.12(15) yes O11 . C12 . H122 . 108.9 no C13 . C12 . H122 . 113.1 no O11 . C12 . H121 . 108.9 no C13 . C12 . H121 . 111.8 no H122 . C12 . H121 . 108.9 no C12 . C13 . N9 . 101.13(15) yes C12 . C13 . H131 . 111.5 no N9 . C13 . H131 . 110.1 no C12 . C13 . H132 . 111.8 no N9 . C13 . H132 . 111.3 no H131 . C13 . H132 . 110.6 no C6 . C15 . C16 . 115.31(18) yes C6 . C15 . H151 . 122.9 no C16 . C15 . H151 . 121.8 no C15 . C16 . C2 . 112.98(18) yes C15 . C16 . H161 . 122.1 no C2 . C16 . H161 . 124.9 no loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 . C2 . 1.6972(19) yes C2 . S3 . 1.780(2) yes C2 . C16 . 1.320(3) yes S3 . O4 . 1.4300(17) yes S3 . O5 . 1.4384(16) yes S3 . C6 . 1.7849(19) yes C6 . C7 . 1.471(3) yes C6 . C15 . 1.340(3) yes C7 . O8 . 1.220(2) yes C7 . N9 . 1.387(2) yes N9 . C10 . 1.395(3) yes N9 . C13 . 1.471(2) yes C10 . O11 . 1.342(2) yes C10 . O14 . 1.201(3) yes O11 . C12 . 1.452(2) yes C12 . C13 . 1.523(3) yes C12 . H122 . 0.965 no C12 . H121 . 0.954 no C13 . H131 . 0.961 no C13 . H132 . 0.959 no C15 . C16 . 1.476(3) yes C15 . H151 . 0.929 no C16 . H161 . 0.935 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C16 . H161 . O5 1_545 165 0.93 2.54 3.453(3) yes C16 . H161 . O8 1_545 121 0.93 2.45 3.037(3) yes