Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds.
Jin, Shengfei; Dang, Hang T.; Haug, Graham C.; He, Ru; Nguyen, Viet D.; Nguyen, Vu T.; Arman, Hadi D.; Schanze, Kirk S.; Larionov, Oleg V.; Journal of the American Chemical Society 142 (2020) 1603–1613; doi:10.1021/jacs.9b12519

data_4133921
_publ_section_title
;
 Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1603
_journal_page_last               1613
_journal_paper_doi               10.1021/jacs.9b12519
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C14 H18 B N O2'
_chemical_formula_sum            'C14 H18 B N O2'
_chemical_formula_weight         243.10
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.721(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3444(5)
_cell_length_b                   9.5619(2)
_cell_length_c                   13.8608(3)
_cell_measurement_reflns_used    16629
_cell_measurement_temperature    98(3)
_cell_measurement_theta_max      29.4680
_cell_measurement_theta_min      2.8980
_cell_volume                     2619.41(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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_temperature      98(3)
_diffrn_detector                 'CCD plate'
_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    -85.00  86.00   1.00   25.00    --    4.20  -9.00-169.00  171
  2  \w    -97.00  18.00   1.00   25.00    --   -7.70 -38.00 -30.00  115
  3  \w    -33.00  82.00   1.00   25.00    --   -7.70  38.00  60.00  115
  4  \w    -97.00  18.00   1.00   25.00    --   -7.70 -38.00  60.00  115
  5  \w    -38.00  -5.00   1.00   25.00    --   -7.70  57.00 -60.00   33
  6  \w    -33.00  82.00   1.00   25.00    --   -7.70  38.00-180.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0018873000
_diffrn_orient_matrix_UB_12      0.0008284000
_diffrn_orient_matrix_UB_13      -0.0504498000
_diffrn_orient_matrix_UB_21      0.0355727000
_diffrn_orient_matrix_UB_22      -0.0090290000
_diffrn_orient_matrix_UB_23      0.0150039000
_diffrn_orient_matrix_UB_31      -0.0043236000
_diffrn_orient_matrix_UB_32      -0.0736218000
_diffrn_orient_matrix_UB_33      -0.0023939000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49501
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.366
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0333P)^2^+2.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5080
_reflns_number_total             5148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cd1902.cif
_cod_data_source_block           cd1902
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_database_code               4133921
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         N1B1O2C20H20
_chemical_oxdiff_usercomment     HDA737-2
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C2(H2), C19(H19), C6(H6), C1(H1A), C16(H16), C21(H21),
 C20(H20), C15(H15)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.070
_oxdiff_exptl_absorpt_empirical_full_min 0.957