Chiral Selenide-Catalyzed, Highly Regio- and Enantioselective Intermolecular Thioarylation of Alkenes with Phenols
Zhang, Yuanyuan; Liang, Yaoyu; Zhao, Xiaodan; ACS Catalysis 11 (2021) 3755–3761; doi:10.1021/acscatal.1c00296

data_4518548
_publ_section_title
;
 Chiral Selenide-Catalyzed, Highly Regio- and Enantioselective
 Intermolecular Thioarylation of Alkenes with Phenols
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3755
_journal_page_last               3761
_journal_paper_doi               10.1021/acscatal.1c00296
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C32 H33 N O5 S2'
_chemical_formula_sum            'C32 H33 N O5 S2'
_chemical_formula_weight         575.71
_chemical_name_systematic        z
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0104(6)
_cell_length_b                   16.6022(10)
_cell_length_c                   18.9828(11)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    150
_cell_measurement_theta_max      52.974
_cell_measurement_theta_min      3.076
_cell_volume                     2839.7(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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_temperature      150.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  multiwire
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15416
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.001
_diffrn_reflns_theta_max         53.001
_diffrn_reflns_theta_min         3.076
_exptl_absorpt_coefficient_mu    1.328
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.6574
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_preparation       a
_exptl_crystal_recrystallization_method a
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.077
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.2983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4468
_reflns_number_total             4958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c00296_si_002.cif
_cod_data_source_block           b19102901a1048_0m
_cod_depositor_comments          'Adding full bibliography for 4518548.cif.'
_cod_database_code               4518548
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.879
_olex2_refinement_description
;
1. 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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3A), C4(H4), C5(H5), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_exptl_crystal_mounting_method a
_olex2_submission_special_instructions 'No special instructions were received'