Photoredox-catalyzed coupling of acyl oxime acetates with thiophenols to give arylthioesters in water at room temperature
Fu, Yuanyuan; Zhu, Shengzhen; Zhao, Xueyan; Huang, Shenlin; Green Chemistry 24 (2022) 6849–6853; doi:10.1039/D2GC02438A

data_7245350
_publ_section_title
;
 Photoredox-catalyzed coupling of acyl oxime acetates with thiophenols to
 give arylthioesters in water at room temperature
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              6849
_journal_page_last               6853
_journal_paper_doi               10.1039/D2GC02438A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C15 H9 Cl2 N O S'
_chemical_formula_sum            'C15 H9 Cl2 N O S'
_chemical_formula_weight         322.19
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2022-05-27 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.152(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3755(11)
_cell_length_b                   7.2951(4)
_cell_length_c                   23.9248(14)
_cell_measurement_reflns_used    4353
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.3660
_cell_measurement_theta_min      2.9150
_cell_volume                     2783.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -18.00   8.00   1.00    2.50    --   11.90 -99.00   0.00   26
  2  \w    -15.00  85.00   1.00    2.50    --   11.90  57.00-150.00  100
  3  \w    -32.00  40.00   1.00    2.50    --   11.90 -19.00  30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205936000
_diffrn_orient_matrix_UB_12      0.0028809000
_diffrn_orient_matrix_UB_13      0.0294615000
_diffrn_orient_matrix_UB_21      0.0351915000
_diffrn_orient_matrix_UB_22      0.0426744000
_diffrn_orient_matrix_UB_23      -0.0072626000
_diffrn_orient_matrix_UB_31      -0.0178977000
_diffrn_orient_matrix_UB_32      0.0871547000
_diffrn_orient_matrix_UB_33      0.0025046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11896
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.555
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0494P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3941
_reflns_number_total             4906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02438a2.cif
_cod_data_source_block           f-1
_cod_depositor_comments          'Adding full bibliography for 7245350.cif.'
_cod_database_code               7245350
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.89
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C19(H19),
 C20(H20), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29)
;
_shelx_res_checksum              875
_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 2.028
_oxdiff_exptl_absorpt_empirical_full_min 0.385