Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols.
Ye, Ke-Yin; McCallum, Terry; Lin, Song; Journal of the American Chemical Society 141 (2019) 9548–9554; doi:10.1021/jacs.9b04993

data_4127464
_publ_section_title
;
 Bimetallic Radical Redox-Relay Catalysis for the Isomerization of
 Epoxides to Allylic Alcohols.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9548
_journal_page_last               9554
_journal_paper_doi               10.1021/jacs.9b04993
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C30 H36 Co F6 N2 O2'
_chemical_formula_sum            'C30 H36 Co F6 N2 O2'
_chemical_formula_weight         629.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.11.15 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5585)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.23860(10)
_cell_length_b                   23.8719(2)
_cell_length_c                   11.73400(10)
_cell_measurement_reflns_used    56721
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.6310
_cell_measurement_theta_min      2.7620
_cell_volume                     2867.96(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -15.00  78.00   0.50    5.10    --    5.64  74.00 -31.00  186
  2  \w    -17.00  68.00   0.50    5.10    --   -5.95  29.00   7.91  170
  3  \w    -26.00  66.00   0.50    5.10    --   -5.95  74.00 -31.00  184
  4  \w    -16.00  69.00   0.50    5.10    --   -5.95  19.00  60.00  170
  5  \w    -26.00  38.00   0.50    5.10    --    5.64 -99.00 -60.00  128
  6  \w    -26.00  26.00   0.50    5.10    --   -5.95 -99.00 -90.00  104
  7  \w    -66.00  26.00   0.50    5.10    --    5.64 -74.00-160.00  184
  8  \w    -17.00  67.00   0.50    5.10    --   -5.95  30.00 -68.33  168
  9  \w    -16.00  69.00   0.50    5.10    --   -5.95  19.00  90.00  170
 10  \w    -26.00  26.00   0.50    5.10    --   -5.95 -99.00  90.00  104
 11  \w    -67.00  17.00   0.50    5.10    --    5.64 -37.00 -30.00  168
 12  \w    -67.00  17.00   0.50    5.10    --    5.64 -37.00 150.00  168
 13  \w    -78.00   5.00   0.50    5.10    --   -5.95 -37.00  30.00  166
 14  \w    -67.00  17.00   0.50    5.10    --    5.64 -32.00-128.66  168
 15  \w    -67.00  17.00   0.50    5.10    --    5.64 -37.00-180.00  168
 16  \w    -78.00  12.00   0.50    5.10    --   -5.95 -74.00-160.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0603167000
_diffrn_orient_matrix_UB_12      -0.0024754000
_diffrn_orient_matrix_UB_13      0.0292785000
_diffrn_orient_matrix_UB_21      -0.0234703000
_diffrn_orient_matrix_UB_22      -0.0242396000
_diffrn_orient_matrix_UB_23      0.0283776000
_diffrn_orient_matrix_UB_31      0.0246477000
_diffrn_orient_matrix_UB_32      -0.0170124000
_diffrn_orient_matrix_UB_33      -0.0446376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            66985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_min         2.164
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.590
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.26a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0194
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+1.6615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0512
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3975
_reflns_number_total             4031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04993_si_002.cif
_cod_data_source_block           rky4_abs
_cod_database_code               4127464
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C30H36CoF6N2O2
_chemical_oxdiff_usercomment     'Crystallized from CH2Cl2/pentane.'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_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:
 C4(H4), C6(H6), C8(H8)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              89076
_shelx_hkl_checksum              6512
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.908