#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:27:53 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263706 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/01/1560151.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_1560151
loop_
_publ_author_name
'Hu, Jiefeng'
'Yang, Xianyu'
'Shi, Shasha'
'Cheng, Bo'
'Luo, Xiaoling'
'Lan, Yu'
'Loh, Teck-Peng'
_publ_section_title
;
 Metal-free C(sp3)--H functionalization of sulfonamides via strain-release
 rearrangement
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              4034
_journal_page_last               4040
_journal_paper_doi               10.1039/D0SC06603F
_journal_volume                  12
_journal_year                    2021
_chemical_formula_sum            'C20 H20 N O2 S2'
_chemical_formula_weight         370.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-25 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.095(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3021(11)
_cell_length_b                   7.9076(7)
_cell_length_c                   18.7346(17)
_cell_measurement_reflns_used    5215
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.80
_cell_volume                     1808.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14733
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.106
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0538
_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/[σ²(Fo²)+(0.0473P)²+1.5676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3112
_reflns_number_total             4132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc06603f2.cif
_cod_data_source_block           20191011LI_SZZ_HFE_12Z_0m_a
_cod_depositor_comments          'Adding full bibliography for 1560151.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1560151
_shelx_shelxl_version_number     2018/3
_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_min   0.938
_shelx_estimated_absorpt_t_max   0.955
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_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 0.52055(6) 0.30006(9) 0.60265(4) 0.03561(19) Uani 1 1 d . . . . .
S2 S 1.05450(5) 0.68587(8) 0.59645(3) 0.02871(17) Uani 1 1 d . . . . .
O1 O 1.03554(15) 0.7342(2) 0.52214(9) 0.0341(4) Uani 1 1 d . . . . .
O2 O 1.14769(15) 0.5811(2) 0.61915(11) 0.0389(5) Uani 1 1 d . . . . .
N14 N 0.94757(18) 0.5894(3) 0.62313(11) 0.0296(5) Uani 1 1 d . . . . .
H14 H 0.945266 0.564879 0.668731 0.036 Uiso 1 1 calc R U . . .
C1 C 0.4156(2) 0.2032(3) 0.54689(15) 0.0330(6) Uani 1 1 d . . . . .
C2 C 0.3186(2) 0.1377(4) 0.56636(17) 0.0416(7) Uani 1 1 d . . . . .
H2 H 0.302467 0.144326 0.614585 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2468(2) 0.0631(4) 0.51381(18) 0.0463(8) Uani 1 1 d . . . . .
H3 H 0.180013 0.017750 0.525959 0.056 Uiso 1 1 calc R U . . .
C4 C 0.2698(2) 0.0525(4) 0.44333(18) 0.0428(7) Uani 1 1 d . . . . .
H4 H 0.218749 -0.000629 0.408170 0.051 Uiso 1 1 calc R U . . .
C5 C 0.3648(2) 0.1175(3) 0.42361(15) 0.0357(6) Uani 1 1 d . . . . .
H5 H 0.379620 0.109827 0.375143 0.043 Uiso 1 1 calc R U . . .
C6 C 0.4397(2) 0.1952(3) 0.47562(14) 0.0304(6) Uani 1 1 d . . . . .
C7 C 0.5417(2) 0.2741(3) 0.46807(14) 0.0310(6) Uani 1 1 d . . . . .
H7 H 0.569693 0.283630 0.423204 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5956(2) 0.3346(3) 0.53065(14) 0.0297(6) Uani 1 1 d . . . . .
C9 C 0.6989(2) 0.4205(3) 0.53460(14) 0.0299(6) Uani 1 1 d . . . . .
H9 H 0.718616 0.455778 0.489455 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7733(2) 0.4598(3) 0.59178(13) 0.0285(5) Uani 1 1 d . . . . .
C11 C 0.7656(2) 0.4125(3) 0.66857(14) 0.0347(6) Uani 1 1 d . . . . .
H11A H 0.839422 0.380947 0.691898 0.042 Uiso 1 1 calc R U . . .
H11B H 0.717894 0.311830 0.669380 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7205(3) 0.5528(4) 0.71199(17) 0.0579(9) Uani 1 1 d . . . . .
H12A H 0.717393 0.513676 0.761317 0.087 Uiso 1 1 calc R U . . .
H12B H 0.646763 0.583297 0.689900 0.087 Uiso 1 1 calc R U . . .
H12C H 0.768457 0.651993 0.712722 0.087 Uiso 1 1 calc R U . . .
C13 C 0.8683(2) 0.5516(3) 0.57514(13) 0.0277(5) Uani 1 1 d . . . . .
H13 H 0.872019 0.585179 0.526816 0.033 Uiso 1 1 calc R U . . .
C17 C 1.0632(2) 0.8698(3) 0.64944(13) 0.0270(5) Uani 1 1 d . . . . .
C18 C 1.1123(2) 0.8633(3) 0.72009(15) 0.0370(6) Uani 1 1 d . . . . .
H18 H 1.137836 0.758849 0.740875 0.044 Uiso 1 1 calc R U . . .
C19 C 1.1236(2) 1.0108(4) 0.75987(14) 0.0380(7) Uani 1 1 d . . . . .
H19 H 1.157355 1.006929 0.808269 0.046 Uiso 1 1 calc R U . . .
C20 C 1.0866(2) 1.1648(3) 0.73045(14) 0.0312(6) Uani 1 1 d . . . . .
C21 C 1.0987(3) 1.3255(4) 0.77340(16) 0.0449(7) Uani 1 1 d . . . . .
H21A H 1.120348 1.417488 0.743047 0.067 Uiso 1 1 calc R U . . .
H21B H 1.155029 1.310336 0.814712 0.067 Uiso 1 1 calc R U . . .
H21C H 1.028783 1.353602 0.790481 0.067 Uiso 1 1 calc R U . . .
C22 C 1.0381(2) 1.1675(3) 0.65937(15) 0.0336(6) Uani 1 1 d . . . . .
H22 H 1.013363 1.271943 0.638171 0.040 Uiso 1 1 calc R U . . .
C23 C 1.0255(2) 1.0214(3) 0.61913(14) 0.0303(6) Uani 1 1 d . . . . .
H23 H 0.991066 1.024820 0.570882 0.036 Uiso 1 1 calc R U . . .
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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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
C1 S1 C8 91.68(13) . . ?
O1 S2 O2 117.98(12) . . ?
O1 S2 N14 112.13(11) . . ?
O2 S2 N14 106.31(11) . . ?
O1 S2 C17 108.61(11) . . ?
O2 S2 C17 108.65(12) . . ?
N14 S2 C17 101.93(12) . . ?
C13 N14 S2 117.57(19) . . ?
C13 N14 H14 121.2 . . ?
S2 N14 H14 121.2 . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 S1 127.3(2) . . ?
C6 C1 S1 111.3(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 129.5(3) . . ?
C1 C6 C7 111.5(2) . . ?
C8 C7 C6 114.2(2) . . ?
C8 C7 H7 122.9 . . ?
C6 C7 H7 122.9 . . ?
C7 C8 C9 123.1(2) . . ?
C7 C8 S1 111.2(2) . . ?
C9 C8 S1 125.69(19) . . ?
C10 C9 C8 131.0(2) . . ?
C10 C9 H9 114.5 . . ?
C8 C9 H9 114.5 . . ?
C9 C10 C13 115.5(2) . . ?
C9 C10 C11 125.7(2) . . ?
C13 C10 C11 118.8(2) . . ?
C10 C11 C12 113.6(2) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N14 C13 C10 122.3(2) . . ?
N14 C13 H13 118.9 . . ?
C10 C13 H13 118.9 . . ?
C23 C17 C18 120.6(2) . . ?
C23 C17 S2 119.47(19) . . ?
C18 C17 S2 119.85(19) . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C22 118.3(2) . . ?
C19 C20 C21 121.5(2) . . ?
C22 C20 C21 120.2(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C20 C22 H22 119.4 . . ?
C22 C23 C17 119.5(2) . . ?
C22 C23 H23 120.2 . . ?
C17 C23 H23 120.2 . . ?
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 1.736(3) . ?
S1 C8 1.748(3) . ?
S2 O1 1.4347(18) . ?
S2 O2 1.4357(19) . ?
S2 N14 1.651(2) . ?
S2 C17 1.757(3) . ?
N14 C13 1.278(3) . ?
N14 H14 0.8800 . ?
C1 C2 1.390(4) . ?
C1 C6 1.405(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.424(4) . ?
C7 C8 1.361(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.435(4) . ?
C9 C10 1.356(3) . ?
C9 H9 0.9500 . ?
C10 C13 1.442(4) . ?
C10 C11 1.501(4) . ?
C11 C12 1.520(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C17 C23 1.382(3) . ?
C17 C18 1.386(4) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C22 1.390(4) . ?
C20 C21 1.502(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
