Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.
Li, Zi-Qi; He, Wen-Ji; Ni, Hui-Qi; Engle, Keary M.; Chemical science 13 (2022) 6567–6572; doi:10.1039/d2sc01563c

data_1566997
_publ_section_title
;
 Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl
 compounds.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              6567
_journal_page_last               6572
_journal_paper_doi               10.1039/d2sc01563c
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H26 N2 O S'
_chemical_formula_sum            'C23 H26 N2 O S'
_chemical_formula_weight         378.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-02-25 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.727(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7413(14)
_cell_length_b                   10.5757(19)
_cell_length_c                   25.507(5)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.988
_cell_measurement_theta_min      2.514
_cell_volume                     2064.1(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19359
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.066
_diffrn_reflns_theta_min         1.615
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1174 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.7773.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.357
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 3468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         8011
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0904P)^2^+0.0712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                7811
_reflns_number_total             8011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01563c3.cif
_cod_data_source_block           pn
_cod_depositor_comments
'Adding full bibliography for 1566996--1566997.cif.'
_cod_database_code               1566997
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.516(2)
 0.484(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C9A(H9A), C8A(H8A), C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C13A(H13A,H13B), C13(H13C,H13D), C11(H11C,H11D)
3.c Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C6A(H6A), C20A(H20A), C16A(H16A), C21A(H21A), C18A(H18A),
 C22A(H22A), C1A(H1AA), C17A(H17A), C5A(H5A), C2A(H2A), N1(H1), C6(H6),
 C22(H22), C16(H16), C2(H2), C1(H1B), C5(H5), C18(H18), C21(H21), C17(H17),
 C20(H20)
3.d Idealised Me refined as rotating group:
 C4A(H4AA,H4AB,H4AC), C10A(H10A,H10B,H10C), C12A(H12A,H12B,H12C), C4(H4A,H4B,
 H4C), C10(H10D,H10E,H10F), C12(H12D,H12E,H12F)
;
_shelx_res_checksum              45417
_olex2_submission_special_instructions 'No special instructions were received'