Rhodium-catalyzed enantioselective C-H alkynylation of sulfoxides in diverse patterns: desymmetrization, kinetic resolution, and parallel kinetic resolution.
Kong, Lingheng; Zou, Yun; Li, Xiao-Xi; Zhang, Xue-Peng; Li, Xingwei; Chemical science 14 (2023) 317–322; doi:10.1039/d2sc05310a

data_1568042
_publ_section_title
;
 Rhodium-catalyzed enantioselective C-H alkynylation of sulfoxides in
 diverse patterns: desymmetrization, kinetic resolution, and parallel
 kinetic resolution.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              317
_journal_page_last               322
_journal_paper_doi               10.1039/d2sc05310a
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_weight         270.33
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-09-17 deposited with the CCDC.	2022-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6856(3)
_cell_length_b                   10.0965(4)
_cell_length_c                   18.0404(8)
_cell_measurement_reflns_used    5370
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.888
_cell_measurement_theta_min      5.762
_cell_volume                     1399.89(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
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_diffrn_measured_fraction_theta_max 0.993
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6756
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.881
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0379P)^2^+0.2155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2638
_reflns_number_total             2740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05310a2.cif
_cod_data_source_block           mo_d8v22234_0m
_cod_depositor_comments
'Adding full bibliography for 1568041--1568042.cif.'
_cod_database_code               1568042
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-4
_shelx_res_checksum              78858