Manganese-Catalyzed C(sp2)‒H Borylation of Furan and Thiophene Derivatives
Britton, Luke; Skrodzki, Maciej; Nichol, Gary S.; Dominey, Andrew P.; Pawluć, Piotr; Docherty, Jamie H.; Thomas, Stephen P.; ACS Catalysis  (2021) 6857–6864; doi:10.1021/acscatal.1c01563

data_4518762
_publ_section_title
;
 Manganese-Catalyzed C(sp2)--H Borylation of Furan and Thiophene
 Derivatives
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              6857
_journal_page_last               6864
_journal_paper_doi               10.1021/acscatal.1c01563
_journal_year                    2021
_chemical_formula_moiety         'C18 H46 B Mn O2 P4'
_chemical_formula_sum            'C18 H46 B Mn O2 P4'
_chemical_formula_weight         484.18
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-15
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.606(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1864(3)
_cell_length_b                   20.8702(7)
_cell_length_c                   13.5759(5)
_cell_measurement_reflns_used    11832
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      29.4870
_cell_measurement_theta_min      3.6630
_cell_volume                     2549.58(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.890
_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      2.00  63.00   1.00   10.00    --   10.76-120.00 135.00   61
  2  \w     22.00  86.00   1.00   10.00    --   10.76-155.00 -21.00   64
  3  \w    -41.00  21.00   1.00   10.00    --   -9.35  77.00   0.00   62
  4  \w    -41.00  21.00   1.00   10.00    --   -9.35  77.00  60.00   62
  5  \w    -40.00  22.00   1.00   10.00    --   -9.35 -77.00   0.00   62
  6  \w    -48.00  29.00   1.00   10.00    --   10.76 -57.00  60.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0099408000
_diffrn_orient_matrix_UB_12      -0.0336988000
_diffrn_orient_matrix_UB_13      -0.0002667000
_diffrn_orient_matrix_UB_21      0.0457480000
_diffrn_orient_matrix_UB_22      0.0016225000
_diffrn_orient_matrix_UB_23      0.0487393000
_diffrn_orient_matrix_UB_31      -0.0634174000
_diffrn_orient_matrix_UB_32      -0.0041027000
_diffrn_orient_matrix_UB_33      0.0216937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28518
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.655
_diffrn_reflns_theta_min         3.305
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method
'The material was recrystallised from hexane by slow evaporation in the freezer.'
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+1.0177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5585
_reflns_number_total             6424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01563_si_003.cif
_cod_data_source_block           se21001
_cod_database_code               4518762
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H46 B1 Mn1 O2 P4'
_chemical_oxdiff_usercomment     '@ 120 K LAB181'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
;
_shelx_res_checksum              34103
_shelx_hkl_checksum              20675
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id LAB181
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.734