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_4133917
_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         'C17 H21 B O3'
_chemical_formula_sum            'C17 H21 B O3'
_chemical_formula_weight         284.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.969(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5926(2)
_cell_length_b                   21.6904(3)
_cell_length_c                   14.3419(2)
_cell_measurement_reflns_used    32389
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.5010
_cell_measurement_theta_min      2.4560
_cell_volume                     3134.44(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (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(2)
_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  34.00   1.00   27.50    --    4.20 -56.00 132.00  119
  2  \w    -33.00  82.00   1.00   27.50    --   -7.70  38.00   0.00  115
  3  \w    -33.00  82.00   1.00   27.50    --   -7.70  38.00-120.00  115
  4  \w    -37.00  82.00   1.00   27.50    --   -7.70  56.00 -85.00  119
  5  \w    -97.00  26.00   1.00   27.50    --   -7.70 -72.00 -60.00  123
  6  \w    -97.00 -22.00   1.00   27.50    --   -7.70 -38.00 120.00   75
  7  \w    -33.00  82.00   1.00   27.50    --   -7.70  38.00  90.00  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      -0.0677846000
_diffrn_orient_matrix_UB_12      0.0068479000
_diffrn_orient_matrix_UB_13      -0.0238887000
_diffrn_orient_matrix_UB_21      -0.0187414000
_diffrn_orient_matrix_UB_22      -0.0207718000
_diffrn_orient_matrix_UB_23      0.0315725000
_diffrn_orient_matrix_UB_31      0.0030178000
_diffrn_orient_matrix_UB_32      0.0243013000
_diffrn_orient_matrix_UB_33      0.0337204000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            67793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         2.229
_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  0.99099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (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    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5250
_reflns_number_total             5545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cd1914a.cif
_cod_data_source_block           cd1914a
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_database_code               4133917
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         B1O2C20H20
_chemical_oxdiff_usercomment     F822-1
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 99.89
_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. Others
 Fixed Sof: O4A(0.7) O5A(0.7) O5B(0.3) O4B(0.3)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C27(H27), C26(H26), C5(H5), C2(H2), C24(H24), C21(H21), C19(H19),
 C3(H3), C7(H7), C8(H8), C22(H22)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C14(H14A,H14B,
 H14C), C13(H13A,H13B,H13C), C34(H34A,H34B,H34C), C33(H33A,H33B,H33C), C30(H30A,
 H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_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 1.048
_oxdiff_exptl_absorpt_empirical_full_min 0.980