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_4133918
_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         'C13 H16 B F3 O2'
_chemical_formula_sum            'C13 H16 B F3 O2'
_chemical_formula_weight         272.07
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                107.497(4)
_cell_angle_beta                 105.684(4)
_cell_angle_gamma                97.298(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4082(5)
_cell_length_b                   8.7515(5)
_cell_length_c                   10.3759(3)
_cell_measurement_reflns_used    10906
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.3090
_cell_measurement_theta_min      2.5080
_cell_volume                     682.79(7)
_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(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    -21.00  94.00   1.00   25.00    --    4.20  38.00-180.00  115
  2  \w    -97.00  18.00   1.00   25.00    --   -7.70 -38.00 -30.00  115
  3  \w    -97.00  26.00   1.00   25.00    --   -7.70 -72.00-120.00  123
  4  \w    -97.00  18.00   1.00   25.00    --   -7.70 -38.00  90.00  115
  5  \w    -41.00  82.00   1.00   25.00    --   -7.70  72.00 -60.00  123
  6  \w    -41.00  82.00   1.00   25.00    --   -7.70  72.00-180.00  123
  7  \w    -41.00  82.00   1.00   25.00    --   -7.70  72.00  60.00  123
  8  \w    -38.00  82.00   1.00   25.00    --   -7.70  57.00-120.00  120
  9  \w    -38.00   1.00   1.00   25.00    --   -7.70  57.00   0.00   39
 10  \w    -33.00  82.00   1.00   25.00    --   -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      0.0666522000
_diffrn_orient_matrix_UB_12      -0.0036511000
_diffrn_orient_matrix_UB_13      -0.0298117000
_diffrn_orient_matrix_UB_21      0.0587624000
_diffrn_orient_matrix_UB_22      0.0138193000
_diffrn_orient_matrix_UB_23      0.0681356000
_diffrn_orient_matrix_UB_31      -0.0140822000
_diffrn_orient_matrix_UB_32      -0.0860773000
_diffrn_orient_matrix_UB_33      -0.0147592000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4483
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.177
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98116
_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    1.323
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0758
_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^)+(0.0100P)^2^+1.3500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3779
_reflns_number_total             4483
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9981\% 
 around [-0.71 0.71 -0.00] (reciprocal) or [-0.73 0.68 0.01] (direct)
;
_cod_data_source_file            cd1883c_twin1_hklf4.cif
_cod_data_source_block           cd1883c_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_original_cell_volume        682.79(6)
_cod_database_code               4133918
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         B1O2F3C8H10
_chemical_oxdiff_usercomment     HDA466-8
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.972
_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:
 C6(H6), C5(H5), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_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 1.071
_oxdiff_exptl_absorpt_empirical_full_min 0.960
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2