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_4133930
_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         'C26 H36 B2 O4'
_chemical_formula_sum            'C26 H36 B2 O4'
_chemical_formula_weight         434.17
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.818(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.2944(14)
_cell_length_b                   6.5162(4)
_cell_length_c                   11.3970(8)
_cell_measurement_reflns_used    5534
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5480
_cell_measurement_theta_min      3.3310
_cell_volume                     1229.44(16)
_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      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -97.00  32.00   1.00   12.50    --   -7.70 -19.00 150.00  129
  2  \w    -97.00  23.00   1.00   12.50    --   -7.70 -57.00  60.00  120
  3  \w    -97.00  18.00   1.00   12.50    --   -7.70 -38.00 -30.00  115
  4  \w    -41.00  82.00   1.00   12.50    --   -7.70  72.00 -90.00  123
  5  \w    -41.00   0.00   1.00   12.50    --   -7.70  72.00  30.00   41
  6  \w    -38.00  82.00   1.00   12.50    --   -7.70  57.00 150.00  120
;
_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      0.0344347000
_diffrn_orient_matrix_UB_12      0.0490802000
_diffrn_orient_matrix_UB_13      0.0392046000
_diffrn_orient_matrix_UB_21      -0.0240711000
_diffrn_orient_matrix_UB_22      0.0858275000
_diffrn_orient_matrix_UB_23      0.0050302000
_diffrn_orient_matrix_UB_31      -0.0082262000
_diffrn_orient_matrix_UB_32      -0.0456294000
_diffrn_orient_matrix_UB_33      0.0516371000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3644
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.461
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88881
_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    1.173
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0200P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2595
_reflns_number_total             3644
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9996\% 
 around [-0.40 -0.00 0.92] (reciprocal) or [-0.00 -0.00 1.00] (direct)
;
_cod_data_source_file            cd1918d_twin1_hklf4.cif
_cod_data_source_block           cd1918d_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_database_code               4133930
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         B2O4C20H20N1
_chemical_oxdiff_usercomment     699-4
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C9(H9A,H9B,H9C), 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 1.102
_oxdiff_exptl_absorpt_empirical_full_min 0.918
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2