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_4035098
_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         'C52 H40 Cl2 F4 O4 Rh2 S4, 2(C H2 Cl2)'
_chemical_formula_sum            'C54 H44 Cl6 F4 O4 Rh2 S4'
_chemical_formula_weight         1379.65
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-11T09:17:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6789(2)
_cell_length_b                   15.7548(3)
_cell_length_c                   27.2450(3)
_cell_measurement_reflns_used    19603
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.239
_cell_measurement_theta_min      3.249
_cell_volume                     5442.29(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Diamond (Brandenburg, K., (1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0682406
_diffrn_orient_matrix_UB_12      -0.0801856
_diffrn_orient_matrix_UB_13      0.0062305
_diffrn_orient_matrix_UB_21      -0.0975328
_diffrn_orient_matrix_UB_22      0.0496553
_diffrn_orient_matrix_UB_23      -0.0176991
_diffrn_orient_matrix_UB_31      0.0243568
_diffrn_orient_matrix_UB_32      -0.0258408
_diffrn_orient_matrix_UB_33      -0.0533379
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            55275
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.398
_diffrn_reflns_theta_max         67.398
_diffrn_reflns_theta_min         3.24
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    9.556
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_correction_T_min  0.149
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
     CrysAlisPro, Rigaku Oxford Diffraction

;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       plate
_exptl_crystal_F_000             2768
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.08
_refine_ls_abs_structure_details
;
 Flack x determined using 3738 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.035(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         9732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+3.2770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0763
_reflns_number_gt                9010
_reflns_number_total             9732
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01269_si_004.cif
_cod_data_source_block           zd6f
_cod_database_code               4035098
_shelx_res_checksum              48979
_shelx_hkl_checksum              41795