Electronic and Steric Tuning of an Atropisomeric Disulfoxide Ligand Motif and Its Use in the Rh(I)-Catalyzed Addition Reactions of Boronic Acids to a Wide Range of Acceptors.
Zhao, Guang-Zhen; Foster, Daven; Sipos, Gellért; Gao, Pengchao; Skelton, Brian W.; Sobolev, Alexandre N.; Dorta, Reto; The Journal of organic chemistry 83 (2018) 9741–9755; doi:10.1021/acs.joc.8b01269

data_4035097
_publ_section_title
;
 Electronic and Steric Tuning of an Atropisomeric Disulfoxide Ligand Motif
 and Its Use in the Rh(I)-Catalyzed Addition Reactions of Boronic Acids to
 a Wide Range of Acceptors.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9741
_journal_page_last               9755
_journal_paper_doi               10.1021/acs.joc.8b01269
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 O2'
_chemical_formula_sum            'C22 H20 O2'
_chemical_formula_weight         316.38
_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-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7770(1)
_cell_length_b                   16.7111(4)
_cell_length_c                   17.3720(4)
_cell_measurement_reflns_used    7472
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.731
_cell_measurement_theta_min      3.668
_cell_volume                     1677.09(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0229827
_diffrn_orient_matrix_UB_12      -0.0877918
_diffrn_orient_matrix_UB_13      0.0259849
_diffrn_orient_matrix_UB_21      -0.0036949
_diffrn_orient_matrix_UB_22      0.0272595
_diffrn_orient_matrix_UB_23      0.0847031
_diffrn_orient_matrix_UB_31      -0.2656338
_diffrn_orient_matrix_UB_32      0.0072315
_diffrn_orient_matrix_UB_33      -0.0034215
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32663
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.236
_diffrn_reflns_theta_max         67.236
_diffrn_reflns_theta_min         3.670
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.85866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0630P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2504
_reflns_number_total             2983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01269_si_005.cif
_cod_data_source_block           df227
_cod_database_code               4035097
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              65895
_shelx_hkl_checksum              7993