Bimetallic Photoredox Catalysis: Visible Light-Promoted Aerobic Hydroxylation of Arylboronic Acids with a Dirhodium(II) Catalyst.
Yang, Hsiang-Ming; Liu, Ming-Lun; Tu, Jing-Wen; Miura-Stempel, Emily; Campbell, Michael G.; Chuang, Gary Jing; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02777

data_4037804
_publ_section_title
;
 Bimetallic Photoredox Catalysis: Visible Light-Promoted Aerobic
 Hydroxylation of Arylboronic Acids with a Dirhodium(II) Catalyst.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02777
_journal_year                    2019
_chemical_formula_moiety         'C28 H28 N4 O8 Rh2'
_chemical_formula_sum            'C28 H28 N4 O8 Rh2'
_chemical_formula_weight         754.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-08-22
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.677(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7654(2)
_cell_length_b                   17.1242(3)
_cell_length_c                   17.5385(3)
_cell_measurement_reflns_used    18911
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      29.2540
_cell_measurement_theta_min      3.6750
_cell_volume                     2823.77(9)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -45.00  14.00   1.00   30.00    --  -14.69 -80.00-157.00   59
  2  \w    -52.00  87.00   1.00   30.00    --   17.27   0.00 -60.00  139
  3  \w    -20.00  56.00   1.00   30.00    --   17.27 -99.00  60.00   76
  4  \w      1.00  85.00   1.00   30.00    --   17.27  57.00 150.00   84
  5  \w    -50.00  34.00   1.00   30.00    --   17.27 -57.00-180.00   84
  6  \w      1.00  85.00   1.00   30.00    --   17.27  57.00 -30.00   84
  7  \w      1.00  85.00   1.00   30.00    --   17.27  57.00  60.00   84
  8  \w    -20.00  56.00   1.00   30.00    --   17.27 -99.00 150.00   76
  9  \w    -20.00  56.00   1.00   30.00    --   17.27 -99.00 -60.00   76
 10  \w     35.00  89.00   1.00   30.00    --   17.27 178.00  30.00   54
 11  \w     35.00  53.00   1.00   30.00    --   17.27 178.00   0.00   18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077926000
_diffrn_orient_matrix_UB_12      0.0411249000
_diffrn_orient_matrix_UB_13      -0.0036994000
_diffrn_orient_matrix_UB_21      0.0207641000
_diffrn_orient_matrix_UB_22      -0.0013512000
_diffrn_orient_matrix_UB_23      -0.0357334000
_diffrn_orient_matrix_UB_31      -0.0720943000
_diffrn_orient_matrix_UB_32      -0.0048272000
_diffrn_orient_matrix_UB_33      -0.0217606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            51946
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.622
_diffrn_reflns_theta_min         3.389
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90572
_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            red
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         7260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0218P)^2^+4.9209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6433
_reflns_number_total             7260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02777_si_002.cif
_cod_data_source_block           Cmpd1
_cod_database_code               4037804
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         C20H20N4O4Rh2
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              30071
_shelx_hkl_checksum              95794
_shelx_fab_checksum              1777
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.868