#------------------------------------------------------------------------------ #$Date: 2021-09-29 01:25:24 +0300 (Wed, 29 Sep 2021) $ #$Revision: 269349 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564739.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_1564739 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 'C15 H16 Cl N O2 S' _chemical_formula_sum 'C15 H16 Cl N O2 S' _chemical_formula_weight 309.80 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-05-03 _audit_creation_method ; Olex2 1.2 (compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492) ; _audit_update_record ; 2021-06-23 deposited with the CCDC. 2021-09-28 downloaded from the CCDC. ; _cell_angle_alpha 99.357(2) _cell_angle_beta 93.406(2) _cell_angle_gamma 90.654(3) _cell_formula_units_Z 2 _cell_length_a 5.5955(2) _cell_length_b 10.7380(3) _cell_length_c 11.8452(3) _cell_measurement_reflns_used 8509 _cell_measurement_temperature 98(2) _cell_measurement_theta_max 30.1250 _cell_measurement_theta_min 2.7880 _cell_volume 700.84(4) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -99.00 20.00 1.00 35.00 -- -9.70 -57.00 -30.00 119 2 \w -34.00 80.00 1.00 35.00 -- -9.70 38.00 120.00 114 3 \w -34.00 80.00 1.00 35.00 -- -9.70 38.00 -90.00 114 4 \w -99.00 20.00 1.00 35.00 -- -9.70 -57.00-180.00 119 5 \w -39.00 80.00 1.00 35.00 -- -9.70 57.00-180.00 119 6 \w -39.00 80.00 1.00 35.00 -- -9.70 57.00 -60.00 119 7 \w -39.00 45.00 1.00 35.00 -- -9.70 57.00 60.00 84 8 \w -34.00 80.00 1.00 35.00 -- -9.70 38.00 0.00 114 ; _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 0.0163832000 _diffrn_orient_matrix_UB_12 0.0392773000 _diffrn_orient_matrix_UB_13 0.0542418000 _diffrn_orient_matrix_UB_21 -0.0869033000 _diffrn_orient_matrix_UB_22 -0.0366378000 _diffrn_orient_matrix_UB_23 0.0219924000 _diffrn_orient_matrix_UB_31 0.0911724000 _diffrn_orient_matrix_UB_32 -0.0399848000 _diffrn_orient_matrix_UB_33 0.0164760000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_unetI/netI 0.0208 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 19342 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_min 2.376 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86797 _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 1.468 _exptl_crystal_description plate _exptl_crystal_F_000 324 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.416 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 3213 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.998 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0398 _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^)+(0.0320P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0902 _refine_ls_wR_factor_ref 0.0904 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3195 _reflns_number_total 3213 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc04245a2.cif _cod_data_source_block cd1690 _cod_database_code 1564739 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula S1Cl1O2N1C20h18 _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 0.947 _shelx_estimated_absorpt_t_min 0.840 _reflns_odcompleteness_completeness 99.94 _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: C10(H10) 2.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C15(H15A,H15B), C14(H14A,H14B), C13(H13A,H13B), C12(H12A,H12B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C5(H5), C4(H4), C8(H8), C9(H9) ; _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 1.149 _oxdiff_exptl_absorpt_empirical_full_min 0.917 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 0.04229(7) 0.19393(4) 0.35837(3) 0.01630(11) Uani 1 1 d . . . . . Cl1 Cl 0.89767(8) 0.16365(5) -0.07162(4) 0.02357(12) Uani 1 1 d . . . . . O1 O 0.0360(2) 0.06261(13) 0.30686(11) 0.0220(3) Uani 1 1 d . . . . . O2 O -0.1743(2) 0.24853(14) 0.40405(11) 0.0234(3) Uani 1 1 d . . . . . N1 N 0.2440(3) 0.44376(14) 0.09685(13) 0.0194(3) Uani 1 1 d . . . . . C6 C 0.3189(3) 0.25109(16) 0.18023(14) 0.0139(3) Uani 1 1 d . . . . . C3 C 0.6763(3) 0.19983(17) 0.02508(14) 0.0163(3) Uani 1 1 d . . . . . C2 C 0.5534(3) 0.30913(17) 0.02652(14) 0.0166(3) Uani 1 1 d . . . . . H2 H 0.590885 0.366461 -0.023376 0.020 Uiso 1 1 calc R . . . . C5 C 0.4551(3) 0.13971(16) 0.17633(14) 0.0159(3) Uani 1 1 d . . . . . H5 H 0.424795 0.082325 0.227229 0.019 Uiso 1 1 calc R . . . . C1 C 0.3695(3) 0.33593(16) 0.10323(14) 0.0150(3) Uani 1 1 d . . . . . C7 C 0.1300(3) 0.28631(16) 0.25421(14) 0.0151(3) Uani 1 1 d . . . . . C4 C 0.6296(3) 0.11422(17) 0.09989(15) 0.0170(3) Uani 1 1 d . . . . . H4 H 0.718665 0.039142 0.097360 0.020 Uiso 1 1 calc R . . . . C8 C 0.0043(3) 0.39332(17) 0.24592(15) 0.0189(4) Uani 1 1 d . . . . . H8 H -0.123179 0.416570 0.294049 0.023 Uiso 1 1 calc R . . . . C10 C 0.2766(3) 0.21997(16) 0.46981(14) 0.0155(3) Uani 1 1 d . . . . . H10 H 0.432694 0.198550 0.435235 0.019 Uiso 1 1 calc R . . . . C11 C 0.2316(3) 0.13065(17) 0.55528(15) 0.0196(4) Uani 1 1 d . . . . . H11A H 0.072624 0.146958 0.586521 0.023 Uiso 1 1 calc R . . . . H11B H 0.231721 0.042083 0.515600 0.023 Uiso 1 1 calc R . . . . C9 C 0.0674(3) 0.46862(17) 0.16459(16) 0.0204(4) Uani 1 1 d . . . . . H9 H -0.023466 0.541693 0.158543 0.024 Uiso 1 1 calc R . . . . C15 C 0.2889(3) 0.35793(17) 0.52835(15) 0.0198(4) Uani 1 1 d . . . . . H15A H 0.324448 0.412931 0.471731 0.024 Uiso 1 1 calc R . . . . H15B H 0.132341 0.382127 0.559097 0.024 Uiso 1 1 calc R . . . . C14 C 0.4840(3) 0.37632(18) 0.62593(15) 0.0204(4) Uani 1 1 d . . . . . H14A H 0.642120 0.360218 0.593805 0.024 Uiso 1 1 calc R . . . . H14B H 0.484690 0.464856 0.665730 0.024 Uiso 1 1 calc R . . . . C13 C 0.4443(3) 0.28788(19) 0.71200(15) 0.0227(4) Uani 1 1 d . . . . . H13A H 0.295292 0.310584 0.750820 0.027 Uiso 1 1 calc R . . . . H13B H 0.579060 0.298316 0.771047 0.027 Uiso 1 1 calc R . . . . C12 C 0.4258(4) 0.15039(18) 0.65329(16) 0.0230(4) Uani 1 1 d . . . . . H12A H 0.388807 0.096151 0.710316 0.028 Uiso 1 1 calc R . . . . H12B H 0.581922 0.124643 0.622801 0.028 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 0.0123(2) 0.0238(2) 0.0130(2) 0.00421(16) 0.00065(14) -0.00489(15) Cl1 0.0194(2) 0.0332(3) 0.0191(2) 0.00510(18) 0.00687(16) 0.00562(17) O1 0.0249(7) 0.0244(7) 0.0166(6) 0.0044(5) -0.0004(5) -0.0092(5) O2 0.0125(6) 0.0395(8) 0.0186(6) 0.0055(6) 0.0035(5) -0.0033(5) N1 0.0201(7) 0.0185(7) 0.0204(7) 0.0059(6) -0.0009(6) 0.0018(6) C6 0.0132(7) 0.0166(8) 0.0121(7) 0.0032(6) -0.0013(6) -0.0020(6) C3 0.0131(8) 0.0224(9) 0.0126(7) 0.0004(6) 0.0012(6) -0.0003(6) C2 0.0169(8) 0.0214(8) 0.0120(7) 0.0050(6) -0.0004(6) -0.0022(6) C5 0.0175(8) 0.0171(8) 0.0137(8) 0.0048(6) -0.0008(6) 0.0000(6) C1 0.0148(8) 0.0164(8) 0.0136(7) 0.0029(6) -0.0021(6) -0.0012(6) C7 0.0125(7) 0.0209(8) 0.0119(7) 0.0039(6) -0.0012(6) -0.0034(6) C4 0.0163(8) 0.0179(8) 0.0162(8) 0.0020(6) -0.0021(6) 0.0024(6) C8 0.0140(8) 0.0240(9) 0.0177(8) 0.0009(7) 0.0007(6) 0.0015(7) C10 0.0121(7) 0.0215(9) 0.0128(7) 0.0033(6) -0.0004(6) -0.0022(6) C11 0.0202(9) 0.0208(9) 0.0187(8) 0.0063(7) 0.0007(7) -0.0028(7) C9 0.0206(9) 0.0182(8) 0.0226(9) 0.0043(7) 0.0004(7) 0.0052(7) C15 0.0209(9) 0.0211(9) 0.0176(8) 0.0055(7) -0.0033(7) -0.0029(7) C14 0.0188(8) 0.0235(9) 0.0179(8) 0.0019(7) -0.0030(7) -0.0026(7) C13 0.0237(9) 0.0290(10) 0.0149(8) 0.0034(7) -0.0018(7) 0.0008(7) C12 0.0255(9) 0.0249(10) 0.0196(9) 0.0082(7) -0.0027(7) 0.0020(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 '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 118.45(8) . . ? O1 S1 C7 108.62(8) . . ? O1 S1 C10 109.08(8) . . ? O2 S1 C7 106.69(8) . . ? O2 S1 C10 108.28(8) . . ? C10 S1 C7 104.89(8) . . ? C9 N1 C1 117.78(15) . . ? C5 C6 C1 118.39(15) . . ? C5 C6 C7 125.72(15) . . ? C1 C6 C7 115.89(15) . . ? C2 C3 Cl1 119.63(14) . . ? C2 C3 C4 121.94(16) . . ? C4 C3 Cl1 118.43(13) . . ? C3 C2 H2 120.4 . . ? C3 C2 C1 119.16(16) . . ? C1 C2 H2 120.4 . . ? C6 C5 H5 119.7 . . ? C4 C5 C6 120.69(16) . . ? C4 C5 H5 119.7 . . ? N1 C1 C6 123.31(16) . . ? N1 C1 C2 116.61(15) . . ? C2 C1 C6 120.06(15) . . ? C6 C7 S1 122.75(13) . . ? C8 C7 S1 117.08(13) . . ? C8 C7 C6 120.15(16) . . ? C3 C4 H4 120.1 . . ? C5 C4 C3 119.73(16) . . ? C5 C4 H4 120.1 . . ? C7 C8 H8 120.6 . . ? C7 C8 C9 118.85(16) . . ? C9 C8 H8 120.6 . . ? S1 C10 H10 108.6 . . ? C11 C10 S1 108.13(11) . . ? C11 C10 H10 108.6 . . ? C15 C10 S1 111.17(12) . . ? C15 C10 H10 108.6 . . ? C15 C10 C11 111.54(14) . . ? C10 C11 H11A 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C12 C11 C10 110.19(14) . . ? C12 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? N1 C9 C8 123.96(17) . . ? N1 C9 H9 118.0 . . ? C8 C9 H9 118.0 . . ? C10 C15 H15A 109.7 . . ? C10 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C14 C15 C10 110.02(15) . . ? C14 C15 H15A 109.7 . . ? C14 C15 H15B 109.7 . . ? C15 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C13 C14 C15 111.54(15) . . ? C13 C14 H14A 109.3 . . ? C13 C14 H14B 109.3 . . ? C14 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C14 C13 C12 111.31(15) . . ? H13A C13 H13B 108.0 . . ? C12 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? C11 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 C11 111.61(15) . . ? C13 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? 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 O1 1.4417(14) . ? S1 O2 1.4477(13) . ? S1 C7 1.7905(17) . ? S1 C10 1.7904(17) . ? Cl1 C3 1.7414(17) . ? N1 C1 1.371(2) . ? N1 C9 1.312(2) . ? C6 C5 1.421(2) . ? C6 C1 1.427(2) . ? C6 C7 1.428(2) . ? C3 C2 1.365(2) . ? C3 C4 1.409(2) . ? C2 H2 0.9500 . ? C2 C1 1.414(2) . ? C5 H5 0.9500 . ? C5 C4 1.371(2) . ? C7 C8 1.368(2) . ? C4 H4 0.9500 . ? C8 H8 0.9500 . ? C8 C9 1.412(3) . ? C10 H10 1.0000 . ? C10 C11 1.533(2) . ? C10 C15 1.529(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.530(2) . ? C9 H9 0.9500 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C14 1.529(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C13 1.526(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C12 1.526(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ?