#------------------------------------------------------------------------------ #$Date: 2021-09-29 01:25:24 +0300 (Wed, 29 Sep 2021) $ #$Revision: 269349 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564737.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_1564737 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_absolute_configuration ad _chemical_formula_moiety 'C14 H21 N O3 S' _chemical_formula_sum 'C14 H21 N O3 S' _chemical_formula_weight 283.38 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-05-17 _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 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.1940(2) _cell_length_b 10.5230(3) _cell_length_c 15.2153(4) _cell_measurement_reflns_used 7797 _cell_measurement_temperature 98(2) _cell_measurement_theta_max 28.6990 _cell_measurement_theta_min 2.5680 _cell_volume 1472.06(7) _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 0.993 _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 -96.00 31.00 1.00 50.00 -- -7.50 -18.00 5.00 127 2 \w -20.00 71.00 1.00 50.00 -- 4.20 38.00 60.00 91 3 \w -89.00 16.00 1.00 50.00 -- -7.50 -38.00-180.00 105 ; _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 0.0726704000 _diffrn_orient_matrix_UB_12 0.0226063000 _diffrn_orient_matrix_UB_13 -0.0000876000 _diffrn_orient_matrix_UB_21 0.0251033000 _diffrn_orient_matrix_UB_22 -0.0614651000 _diffrn_orient_matrix_UB_23 0.0116774000 _diffrn_orient_matrix_UB_31 0.0063495000 _diffrn_orient_matrix_UB_32 -0.0159001000 _diffrn_orient_matrix_UB_33 -0.0451411000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0298 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 14833 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_min 2.353 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94384 _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 1.279 _exptl_crystal_description block _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.291 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details ; Flack x determined using 1288 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 3329 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0333 _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^)+(0.0400P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.0786 _reflns_Friedel_coverage 0.732 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.979 _reflns_number_gt 3267 _reflns_number_total 3329 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc04245a2.cif _cod_data_source_block cd1695c _cod_database_code 1564737 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_formula C12H20NSO2 _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 0.993 _shelx_estimated_absorpt_t_min 0.930 _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Riding coordinates: N1(H1) 2.b Ternary CH refined with riding coordinates: C6(H6), C1(H1A) 2.c Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C2(H2A,H2B) 2.d Aromatic/amide H refined with riding coordinates: C8(H8), C11(H11), C12(H12), C9(H9) 2.e Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C) ; _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 1.097 _oxdiff_exptl_absorpt_empirical_full_min 0.869 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -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 0.41468(5) 0.71705(5) 0.42625(3) 0.01297(13) Uani 1 1 d . . . . . O2 O 0.51436(18) 0.80521(16) 0.38595(10) 0.0197(4) Uani 1 1 d . . . . . O1 O 0.26144(15) 0.74770(16) 0.42545(11) 0.0217(4) Uani 1 1 d . . . . . O3 O 0.60775(17) 0.11855(15) 0.59236(10) 0.0197(4) Uani 1 1 d . . . . . N1 N 0.46402(19) 0.70502(17) 0.52742(11) 0.0134(4) Uani 1 1 d . . . . . H1 H 0.555890 0.689991 0.529691 0.016 Uiso 1 1 d R . . . . C7 C 0.4430(2) 0.4881(2) 0.59214(12) 0.0133(4) Uani 1 1 d . . . . . C6 C 0.3883(2) 0.6237(2) 0.59252(13) 0.0146(4) Uani 1 1 d . . . . . H6 H 0.282284 0.622793 0.577842 0.018 Uiso 1 1 calc R . . . . C8 C 0.3489(2) 0.3863(2) 0.58057(14) 0.0154(4) Uani 1 1 d . . . . . H8 H 0.248072 0.402591 0.572684 0.018 Uiso 1 1 calc R . . . . C11 C 0.6421(3) 0.3377(2) 0.60289(14) 0.0167(5) Uani 1 1 d . . . . . H11 H 0.743050 0.321462 0.610310 0.020 Uiso 1 1 calc R . . . . C12 C 0.5911(3) 0.4612(2) 0.60359(13) 0.0149(4) Uani 1 1 d . . . . . H12 H 0.657702 0.529159 0.611983 0.018 Uiso 1 1 calc R . . . . C9 C 0.3979(2) 0.2609(2) 0.58016(14) 0.0172(4) Uani 1 1 d . . . . . H9 H 0.331238 0.192819 0.572367 0.021 Uiso 1 1 calc R . . . . C10 C 0.5456(2) 0.2367(2) 0.59130(13) 0.0156(4) Uani 1 1 d . . . . . C1 C 0.4314(2) 0.5664(2) 0.37408(14) 0.0152(4) Uani 1 1 d . . . . . H1A H 0.367053 0.503504 0.404324 0.018 Uiso 1 1 calc R . . . . C3 C 0.6290(3) 0.4931(3) 0.27813(15) 0.0267(6) Uani 1 1 d . . . . . H3A H 0.733009 0.511402 0.266923 0.032 Uiso 1 1 calc R . . . . H3B H 0.608558 0.403867 0.261701 0.032 Uiso 1 1 calc R . . . . C13 C 0.4072(3) 0.6870(2) 0.68238(14) 0.0214(5) Uani 1 1 d . . . . . H13A H 0.511008 0.697692 0.694847 0.032 Uiso 1 1 calc GR . . . . H13B H 0.362998 0.633421 0.727830 0.032 Uiso 1 1 calc GR . . . . H13C H 0.359534 0.770278 0.682010 0.032 Uiso 1 1 calc GR . . . . C4 C 0.5318(3) 0.5842(3) 0.22712(15) 0.0243(6) Uani 1 1 d . . . . . H4A H 0.520905 0.556719 0.165236 0.029 Uiso 1 1 calc R . . . . H4B H 0.571261 0.671702 0.228367 0.029 Uiso 1 1 calc R . . . . C5 C 0.3875(3) 0.5762(3) 0.27605(15) 0.0223(5) Uani 1 1 d . . . . . H5A H 0.331642 0.500463 0.257459 0.027 Uiso 1 1 calc R . . . . H5B H 0.328007 0.653109 0.265382 0.027 Uiso 1 1 calc R . . . . C2 C 0.5901(3) 0.5176(2) 0.37526(14) 0.0211(5) Uani 1 1 d . . . . . H2A H 0.655860 0.582113 0.401090 0.025 Uiso 1 1 calc R . . . . H2B H 0.597812 0.438346 0.409960 0.025 Uiso 1 1 calc R . . . . C14 C 0.5130(3) 0.0119(2) 0.5840(2) 0.0330(7) Uani 1 1 d . . . . . H14A H 0.463579 0.015230 0.527010 0.049 Uiso 1 1 calc GR . . . . H14B H 0.440559 0.013826 0.631261 0.049 Uiso 1 1 calc GR . . . . H14C H 0.569766 -0.066734 0.588101 0.049 Uiso 1 1 calc GR . . . . 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 0.0115(2) 0.0116(2) 0.0159(2) 0.0030(2) -0.00036(19) 0.0006(2) O2 0.0222(8) 0.0177(9) 0.0192(8) 0.0052(7) 0.0014(6) -0.0055(7) O1 0.0147(7) 0.0242(9) 0.0263(8) 0.0038(7) -0.0006(6) 0.0065(6) O3 0.0192(9) 0.0113(7) 0.0285(9) -0.0007(6) 0.0039(7) -0.0003(7) N1 0.0116(8) 0.0128(9) 0.0157(8) 0.0014(7) -0.0002(6) -0.0001(7) C7 0.0162(11) 0.0156(10) 0.0079(9) 0.0013(8) 0.0002(7) -0.0015(8) C6 0.0136(10) 0.0143(10) 0.0159(10) 0.0010(8) 0.0019(8) -0.0026(8) C8 0.0110(9) 0.0174(11) 0.0177(10) 0.0011(9) -0.0005(9) -0.0015(8) C11 0.0132(10) 0.0190(12) 0.0181(10) 0.0030(9) -0.0009(8) -0.0011(9) C12 0.0150(10) 0.0138(10) 0.0160(9) 0.0023(8) -0.0034(9) -0.0060(9) C9 0.0154(10) 0.0153(10) 0.0208(10) -0.0010(8) -0.0005(9) -0.0068(9) C10 0.0203(10) 0.0139(11) 0.0127(10) 0.0003(8) 0.0028(8) 0.0002(9) C1 0.0146(10) 0.0135(10) 0.0174(10) -0.0013(8) 0.0001(8) -0.0003(9) C3 0.0269(13) 0.0332(15) 0.0199(11) -0.0094(11) 0.0031(10) 0.0054(11) C13 0.0286(12) 0.0187(11) 0.0169(10) -0.0026(9) 0.0062(10) -0.0021(11) C4 0.0257(12) 0.0316(15) 0.0155(11) -0.0048(10) 0.0012(9) -0.0030(11) C5 0.0212(12) 0.0287(14) 0.0170(11) -0.0012(9) -0.0041(9) -0.0040(11) C2 0.0214(11) 0.0242(12) 0.0175(10) -0.0031(9) -0.0008(10) 0.0084(11) C14 0.0287(14) 0.0125(12) 0.0577(19) -0.0060(12) 0.0039(13) -0.0024(10) 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' 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 O2 S1 O1 118.21(10) . . ? O2 S1 N1 106.16(9) . . ? O2 S1 C1 109.19(10) . . ? O1 S1 N1 107.47(9) . . ? O1 S1 C1 106.22(10) . . ? N1 S1 C1 109.40(10) . . ? C10 O3 C14 117.31(18) . . ? S1 N1 H1 109.2 . . ? C6 N1 S1 123.50(14) . . ? C6 N1 H1 109.2 . . ? C8 C7 C6 121.40(19) . . ? C8 C7 C12 117.8(2) . . ? C12 C7 C6 120.84(18) . . ? N1 C6 C7 112.70(17) . . ? N1 C6 H6 108.3 . . ? N1 C6 C13 107.01(17) . . ? C7 C6 H6 108.3 . . ? C7 C6 C13 112.09(17) . . ? C13 C6 H6 108.3 . . ? C7 C8 H8 119.0 . . ? C7 C8 C9 121.96(19) . . ? C9 C8 H8 119.0 . . ? C12 C11 H11 120.0 . . ? C12 C11 C10 120.1(2) . . ? C10 C11 H11 120.0 . . ? C7 C12 H12 119.4 . . ? C11 C12 C7 121.2(2) . . ? C11 C12 H12 119.4 . . ? C8 C9 H9 120.4 . . ? C10 C9 C8 119.20(19) . . ? C10 C9 H9 120.4 . . ? O3 C10 C11 115.12(19) . . ? O3 C10 C9 125.1(2) . . ? C9 C10 C11 119.8(2) . . ? S1 C1 H1A 109.5 . . ? C5 C1 S1 110.34(16) . . ? C5 C1 H1A 109.5 . . ? C2 C1 S1 111.83(15) . . ? C2 C1 H1A 109.5 . . ? C2 C1 C5 106.20(17) . . ? H3A C3 H3B 108.9 . . ? C4 C3 H3A 110.9 . . ? C4 C3 H3B 110.9 . . ? C4 C3 C2 104.30(19) . . ? C2 C3 H3A 110.9 . . ? C2 C3 H3B 110.9 . . ? C6 C13 H13A 109.5 . . ? C6 C13 H13B 109.5 . . ? C6 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 C4 H4A 111.1 . . ? C3 C4 H4B 111.1 . . ? C3 C4 C5 103.1(2) . . ? H4A C4 H4B 109.1 . . ? C5 C4 H4A 111.1 . . ? C5 C4 H4B 111.1 . . ? C1 C5 H5A 110.9 . . ? C1 C5 H5B 110.9 . . ? C4 C5 C1 104.33(18) . . ? C4 C5 H5A 110.9 . . ? C4 C5 H5B 110.9 . . ? H5A C5 H5B 108.9 . . ? C1 C2 H2A 110.7 . . ? C1 C2 H2B 110.7 . . ? C3 C2 C1 105.26(18) . . ? C3 C2 H2A 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 O2 1.4409(16) . ? S1 O1 1.4454(15) . ? S1 N1 1.6098(17) . ? S1 C1 1.780(2) . ? O3 C10 1.368(3) . ? O3 C14 1.427(3) . ? N1 H1 0.8600 . ? N1 C6 1.483(3) . ? C7 C6 1.513(3) . ? C7 C8 1.388(3) . ? C7 C12 1.402(3) . ? C6 H6 1.0000 . ? C6 C13 1.531(3) . ? C8 H8 0.9500 . ? C8 C9 1.395(3) . ? C11 H11 0.9500 . ? C11 C12 1.382(3) . ? C11 C10 1.396(3) . ? C12 H12 0.9500 . ? C9 H9 0.9500 . ? C9 C10 1.392(3) . ? C1 H1A 1.0000 . ? C1 C5 1.549(3) . ? C1 C2 1.547(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.523(4) . ? C3 C2 1.542(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.523(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ?