Cu-Catalyzed Photoredox Chlorosulfonation of Alkenes and Alkynes.
Alkan-Zambada, Murat; Hu, Xile; The Journal of organic chemistry 84 (2019) 4525–4533; doi:10.1021/acs.joc.9b00238

data_4034273
_publ_section_title
;
 Cu-Catalyzed Photoredox Chlorosulfonation of Alkenes and Alkynes.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4525
_journal_page_last               4533
_journal_paper_doi               10.1021/acs.joc.9b00238
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C20 H14 Cl F O2 S'
_chemical_formula_sum            'C20 H14 Cl F O2 S'
_chemical_formula_weight         372.82
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                91.916(5)
_cell_angle_beta                 92.417(5)
_cell_angle_gamma                104.915(5)
_cell_formula_units_Z            4
_cell_length_a                   9.3502(6)
_cell_length_b                   9.7552(5)
_cell_length_c                   18.8817(13)
_cell_measurement_reflns_used    2697
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      73.3480
_cell_measurement_theta_min      5.1450
_cell_volume                     1661.00(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_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   -109.00 -18.00   1.00    1.50    --  -43.01 -57.00 150.00   91
  2  \w    -63.00  30.00   1.00    1.50    --  -43.01  57.00 -60.00   93
  3  \w    -70.00  19.00   1.00    1.50    --  -43.01  57.00  90.00   89
  4  \w     71.00  98.00   1.00    1.50    --   43.01-125.00 -60.00   27
  5  \w     81.00 135.00   1.00    6.00    --  105.68 -61.00 120.00   54
  6  \w     53.00 126.00   1.00    6.00    --  105.68 -45.00  90.00   73
  7  \w     61.00 110.00   1.00    6.00    --  105.68 -77.00 -90.00   49
  8  \w     36.00 131.00   1.00    6.00    --  105.68 -45.00 -90.00   95
  9  \w     51.00 132.00   1.00    6.00    --  105.68 -45.00   0.00   81
 10  \w     43.00 118.00   1.00    6.00    --  105.68-125.00 -60.00   75
 11  \w    130.00 178.00   1.00    6.00    --  105.68  61.00  60.00   48
 12  \w     96.00 123.00   1.00    6.00    --  105.68 125.00-150.00   27
 13  \w     57.00 108.00   1.00    6.00    --  105.68 -94.00 120.00   51
 14  \w     58.00 106.00   1.00    6.00    --  105.68 -94.00  30.00   48
 15  \w     19.00 178.00   1.00    6.00    --  105.68   0.00-120.00  159
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1350652000
_diffrn_orient_matrix_UB_12      0.0210782000
_diffrn_orient_matrix_UB_13      -0.0436386000
_diffrn_orient_matrix_UB_21      0.0534720000
_diffrn_orient_matrix_UB_22      -0.0625598000
_diffrn_orient_matrix_UB_23      -0.0668267000
_diffrn_orient_matrix_UB_31      -0.0897300000
_diffrn_orient_matrix_UB_32      -0.1496897000
_diffrn_orient_matrix_UB_33      0.0176856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6731
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.520
_diffrn_reflns_theta_min         4.693
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.401
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.346
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model/Empirical absorption correction using
 spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.648
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0786P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4978
_reflns_number_total             6731
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9605\% 
 around [-0.24 0.97 -0.06] (reciprocal) or [-0.00 1.00 -0.00] (direct)
;
_cod_data_source_file            jo9b00238_si_002.cif
_cod_data_source_block           MA-3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034273
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C20 H14 Cl F O2 S'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4429(15)
 0.5571(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C27(H27), C30(H30), C31(H31), C33(H33), C34(H34),
 C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
;
_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 2.119
_oxdiff_exptl_absorpt_empirical_full_min 0.822
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2