#------------------------------------------------------------------------------ #$Date: 2021-09-29 01:25:24 +0300 (Wed, 29 Sep 2021) $ #$Revision: 269349 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564736.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_1564736 loop_ _publ_author_name 'Jin, Shengfei' 'Haug, Graham C.' 'Trevino, Ramon' 'Nguyen, Viet D.' 'Arman, Hadi' 'Larionov, Oleg V.' _publ_section_title ; Photoinduced C(sp3)--H Sulfination Empowers a Direct and Chemoselective Introduction of the Sulfonyl Group ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC04245A _journal_year 2021 _chemical_formula_moiety 'C13 H18 O3 S' _chemical_formula_sum 'C13 H18 O3 S' _chemical_formula_weight 254.33 _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 2018-04-19 _audit_creation_method ; Olex2 1.2 (compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488) ; _audit_update_record ; 2021-06-23 deposited with the CCDC. 2021-09-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.051(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.8529(2) _cell_length_b 9.2662(3) _cell_length_c 19.1898(5) _cell_measurement_reflns_used 4836 _cell_measurement_temperature 98(2) _cell_measurement_theta_max 30.2930 _cell_measurement_theta_min 3.0420 _cell_volume 1218.56(6) _computing_cell_refinement 'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.28e (Rigaku OD, 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 98(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _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 -42.00 80.00 1.00 35.00 -- -9.70 69.00 -26.00 122 2 \w -34.00 80.00 1.00 35.00 -- -9.70 38.00 90.00 114 3 \w -99.00 -74.00 1.00 35.00 -- -9.70 -72.00 120.00 25 4 \w -34.00 80.00 1.00 35.00 -- -9.70 38.00-150.00 114 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RCD3): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0139358000 _diffrn_orient_matrix_UB_12 -0.0029448000 _diffrn_orient_matrix_UB_13 0.0365864000 _diffrn_orient_matrix_UB_21 -0.0645250000 _diffrn_orient_matrix_UB_22 -0.0597520000 _diffrn_orient_matrix_UB_23 0.0019933000 _diffrn_orient_matrix_UB_31 0.0797817000 _diffrn_orient_matrix_UB_32 -0.0477517000 _diffrn_orient_matrix_UB_33 -0.0047438000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_unetI/netI 0.0209 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 13700 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_min 2.441 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.386 _exptl_crystal_description plate _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.453 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2778 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0405 _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^)+(0.0300P)^2^+1.4500P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.0894 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2728 _reflns_number_total 2778 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc04245a2.cif _cod_data_source_block cd1683c _cod_database_code 1564736 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula S1o4C20H20 _chemical_oxdiff_usercomment 'bicyclooctane with C=O' _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 0.982 _shelx_estimated_absorpt_t_min 0.912 _reflns_odcompleteness_completeness 99.56 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.42 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Ternary CH refined with riding coordinates: C8(H8), C3(H3), C5(H5) 2.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C9(H9A,H9B), C2(H2A,H2B), C7(H7A,H7B), C10(H10A,H10B), C4(H4A, H4B) 2.c Aromatic/amide H refined with riding coordinates: C12(H12) 2.d X=CH2 refined with riding coordinates: C13(H13A,H13B) ; _olex2_exptl_crystal_mounting_method 'nylon loop' _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 1.072 _oxdiff_exptl_absorpt_empirical_full_min 0.928 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 0.74710(5) 0.28508(4) 0.77991(2) 0.01020(11) Uani 1 1 d . . . . . O1 O 0.69012(17) 0.43412(12) 0.78819(6) 0.0154(2) Uani 1 1 d . . . . . O3 O 0.46996(16) 0.32965(12) 0.66170(6) 0.0143(2) Uani 1 1 d . . . . . O2 O 0.91516(17) 0.23558(13) 0.81903(6) 0.0174(3) Uani 1 1 d . . . . . C6 C 0.6293(2) 0.29143(16) 0.64122(8) 0.0105(3) Uani 1 1 d . . . . . C1 C 0.7999(2) 0.25150(16) 0.68879(7) 0.0094(3) Uani 1 1 d . . . . . C11 C 0.5474(2) 0.17008(18) 0.80215(8) 0.0149(3) Uani 1 1 d . . . . . H11A H 0.429928 0.198640 0.775456 0.018 Uiso 1 1 calc R . . . . H11B H 0.579451 0.068877 0.790209 0.018 Uiso 1 1 calc R . . . . C8 C 1.0309(2) 0.32178(17) 0.59266(8) 0.0135(3) Uani 1 1 d . . . . . H8 H 1.146684 0.382271 0.580315 0.016 Uiso 1 1 calc R . . . . C9 C 1.0806(2) 0.16207(18) 0.58112(8) 0.0150(3) Uani 1 1 d . . . . . H9A H 1.117849 0.146213 0.531872 0.018 Uiso 1 1 calc R . . . . H9B H 1.192530 0.134405 0.610918 0.018 Uiso 1 1 calc R . . . . C2 C 0.8498(2) 0.09042(16) 0.67630(8) 0.0125(3) Uani 1 1 d . . . . . H2A H 0.960901 0.061571 0.706244 0.015 Uiso 1 1 calc R . . . . H2B H 0.736241 0.029374 0.688401 0.015 Uiso 1 1 calc R . . . . C12 C 0.5082(2) 0.18253(18) 0.87864(8) 0.0149(3) Uani 1 1 d . . . . . H12 H 0.610965 0.161136 0.910248 0.018 Uiso 1 1 calc R . . . . C3 C 0.9033(2) 0.06905(17) 0.59919(8) 0.0140(3) Uani 1 1 d . . . . . H3 H 0.936111 -0.034744 0.591080 0.017 Uiso 1 1 calc R . . . . C7 C 0.9778(2) 0.34719(17) 0.66934(8) 0.0122(3) Uani 1 1 d . . . . . H7A H 0.945288 0.450157 0.676743 0.015 Uiso 1 1 calc R . . . . H7B H 1.090282 0.322562 0.699463 0.015 Uiso 1 1 calc R . . . . C5 C 0.6791(2) 0.27151(18) 0.56501(8) 0.0147(3) Uani 1 1 d . . . . . H5 H 0.565334 0.299830 0.535348 0.018 Uiso 1 1 calc R . . . . C10 C 0.8585(2) 0.36421(18) 0.54618(8) 0.0155(3) Uani 1 1 d . . . . . H10A H 0.893050 0.349151 0.496627 0.019 Uiso 1 1 calc R . . . . H10B H 0.827559 0.467641 0.552880 0.019 Uiso 1 1 calc R . . . . C13 C 0.3382(2) 0.22166(19) 0.90415(9) 0.0186(3) Uani 1 1 d . . . . . H13A H 0.233214 0.243600 0.873592 0.022 Uiso 1 1 calc R . . . . H13B H 0.320459 0.227987 0.953149 0.022 Uiso 1 1 calc R . . . . C4 C 0.7281(2) 0.11045(18) 0.55351(8) 0.0163(3) Uani 1 1 d . . . . . H4A H 0.614059 0.050140 0.565892 0.020 Uiso 1 1 calc R . . . . H4B H 0.759571 0.093385 0.503851 0.020 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 0.01095(19) 0.01030(19) 0.00936(17) -0.00106(13) -0.00179(13) -0.00114(14) O1 0.0189(6) 0.0117(6) 0.0156(5) -0.0033(4) -0.0004(4) -0.0002(4) O3 0.0102(5) 0.0157(6) 0.0170(6) -0.0001(4) -0.0012(4) 0.0012(4) O2 0.0164(6) 0.0221(6) 0.0138(5) -0.0003(5) -0.0049(4) 0.0029(5) C6 0.0126(7) 0.0070(7) 0.0120(7) 0.0002(5) -0.0021(5) -0.0018(6) C1 0.0092(7) 0.0105(7) 0.0086(6) -0.0002(5) -0.0008(5) 0.0004(5) C11 0.0171(8) 0.0149(8) 0.0127(7) 0.0002(6) 0.0015(6) -0.0051(6) C8 0.0122(7) 0.0138(8) 0.0145(7) 0.0010(6) 0.0025(6) -0.0011(6) C9 0.0138(8) 0.0161(8) 0.0150(7) 0.0002(6) 0.0028(6) 0.0023(6) C2 0.0149(8) 0.0096(7) 0.0131(7) 0.0001(6) 0.0024(6) 0.0016(6) C12 0.0158(8) 0.0179(8) 0.0110(7) 0.0021(6) -0.0017(6) -0.0005(6) C3 0.0175(8) 0.0096(7) 0.0149(7) -0.0021(6) 0.0027(6) 0.0009(6) C7 0.0111(7) 0.0122(7) 0.0133(7) -0.0008(6) -0.0007(6) -0.0018(6) C5 0.0132(8) 0.0195(8) 0.0113(7) 0.0004(6) -0.0028(6) 0.0016(6) C10 0.0178(8) 0.0165(8) 0.0122(7) 0.0034(6) 0.0017(6) 0.0022(6) C13 0.0177(8) 0.0202(9) 0.0178(8) -0.0020(6) -0.0003(6) 0.0026(7) C4 0.0181(8) 0.0191(8) 0.0119(7) -0.0050(6) 0.0003(6) -0.0031(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 O1 S1 O2 117.43(7) . . ? O1 S1 C1 108.93(7) . . ? O1 S1 C11 109.70(8) . . ? O2 S1 C1 106.64(7) . . ? O2 S1 C11 107.23(8) . . ? C11 S1 C1 106.35(7) . . ? O3 C6 C1 124.43(13) . . ? O3 C6 C5 123.52(14) . . ? C5 C6 C1 112.00(12) . . ? C6 C1 S1 112.43(10) . . ? C6 C1 C2 108.05(12) . . ? C6 C1 C7 108.56(12) . . ? C2 C1 S1 111.02(10) . . ? C2 C1 C7 109.82(12) . . ? C7 C1 S1 106.93(10) . . ? S1 C11 H11A 109.9 . . ? S1 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? C12 C11 S1 109.06(11) . . ? C12 C11 H11A 109.9 . . ? C12 C11 H11B 109.9 . . ? C9 C8 H8 109.3 . . ? C7 C8 H8 109.3 . . ? C7 C8 C9 109.83(13) . . ? C10 C8 H8 109.3 . . ? C10 C8 C9 109.56(13) . . ? C10 C8 C7 109.60(13) . . ? C8 C9 H9A 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C3 C9 C8 109.51(13) . . ? C3 C9 H9A 109.8 . . ? C3 C9 H9B 109.8 . . ? C1 C2 H2A 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C3 C2 C1 109.00(12) . . ? C3 C2 H2A 109.9 . . ? C3 C2 H2B 109.9 . . ? C11 C12 H12 118.4 . . ? C13 C12 C11 123.12(15) . . ? C13 C12 H12 118.4 . . ? C9 C3 C2 109.61(13) . . ? C9 C3 H3 109.1 . . ? C9 C3 C4 110.53(13) . . ? C2 C3 H3 109.1 . . ? C4 C3 C2 109.32(13) . . ? C4 C3 H3 109.1 . . ? C1 C7 H7A 109.8 . . ? C1 C7 H7B 109.8 . . ? C8 C7 C1 109.27(12) . . ? C8 C7 H7A 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C6 C5 H5 110.0 . . ? C6 C5 C10 109.81(13) . . ? C6 C5 C4 107.75(13) . . ? C10 C5 H5 110.0 . . ? C10 C5 C4 109.33(13) . . ? C4 C5 H5 110.0 . . ? C8 C10 C5 109.59(13) . . ? C8 C10 H10A 109.8 . . ? C8 C10 H10B 109.8 . . ? C5 C10 H10A 109.8 . . ? C5 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? C12 C13 H13A 120.0 . . ? C12 C13 H13B 120.0 . . ? H13A C13 H13B 120.0 . . ? C3 C4 C5 109.26(13) . . ? C3 C4 H4A 109.8 . . ? C3 C4 H4B 109.8 . . ? C5 C4 H4A 109.8 . . ? C5 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? 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 O1 1.4440(12) . ? S1 O2 1.4487(12) . ? S1 C1 1.8128(15) . ? S1 C11 1.7862(16) . ? O3 C6 1.2136(19) . ? C6 C1 1.528(2) . ? C6 C5 1.513(2) . ? C1 C2 1.550(2) . ? C1 C7 1.553(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.497(2) . ? C8 H8 1.0000 . ? C8 C9 1.535(2) . ? C8 C7 1.534(2) . ? C8 C10 1.531(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C3 1.530(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.537(2) . ? C12 H12 0.9500 . ? C12 C13 1.315(2) . ? C3 H3 1.0000 . ? C3 C4 1.534(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C5 H5 1.0000 . ? C5 C10 1.543(2) . ? C5 C4 1.546(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C13 H13A 0.9500 . ? C13 H13B 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ?