Copper-catalyzed direct sulfenoamination of saturated ketones <i>via in situ</i> formed enaminones.
Wang, Jiateng; Zhuang, Yunqing; Zhao, Jie; Bi, Yusong; Li, Chunyan; Bi, Gehua; Yang, Kai; Huang, Xin; Zhang, Weimin; Organic & biomolecular chemistry 20 (2022) 1749–1753; doi:10.1039/d1ob02469h

data_7158515
_publ_section_title
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 Copper-catalyzed direct sulfenoamination of saturated ketones <i>via in
 situ</i> formed enaminones.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1749
_journal_page_last               1753
_journal_paper_doi               10.1039/d1ob02469h
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C20 H20 Cl N O2 S'
_chemical_formula_sum            'C20 H20 Cl N O2 S'
_chemical_formula_weight         373.88
_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_block_doi                 10.5517/ccdc.csd.cc29856z
_audit_creation_date             2021-08-21
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_audit_update_record
;
2021-11-19 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.685(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4606(5)
_cell_length_b                   15.2394(8)
_cell_length_c                   13.4503(8)
_cell_measurement_reflns_used    6070
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      58.983
_cell_measurement_theta_min      3.018
_cell_volume                     1836.98(18)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14195
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.251
_diffrn_reflns_theta_min         3.934
_diffrn_source_current           2.85
_diffrn_source_power             0.1986735
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.5606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1197 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.7457.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0622P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2865
_reflns_number_total             3942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02469h2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7158515.cif.'
_cod_database_code               7158515
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.826
_shelx_estimated_absorpt_t_min   0.797
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              62447
_olex2_submission_special_instructions 'No special instructions were received'