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_4133915
_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         'C25 H34 B2 O4'
_chemical_formula_sum            'C25 H34 B2 O4'
_chemical_formula_weight         420.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                90
_cell_angle_beta                 112.921(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.3806(6)
_cell_length_b                   6.61660(10)
_cell_length_c                   31.0990(8)
_cell_measurement_reflns_used    35678
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      28.4540
_cell_measurement_theta_min      2.6200
_cell_volume                     4810.2(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  30.00   1.00   58.00    --    4.20 -42.00 -22.00  115
  2  \w    -33.00  82.00   1.00   58.00    --   -7.70  42.00 129.00  115
  3  \w    -97.00  26.00   1.00   58.00    --   -7.70 -72.00  30.00  123
  4  \w    -97.00  18.00   1.00   58.00    --   -7.70 -38.00 -60.00  115
  5  \w    -97.00  18.00   1.00   58.00    --   -7.70 -38.00 150.00  115
  6  \w    -97.00  18.00   1.00   58.00    --   -7.70 -38.00-180.00  115
  7  \w    -41.00  82.00   1.00   58.00    --   -7.70  72.00   0.00  123
  8  \w    -41.00  82.00   1.00   58.00    --   -7.70  72.00-180.00  123
  9  \w    -41.00  82.00   1.00   58.00    --   -7.70  72.00  90.00  123
 10  \w    -41.00  82.00   1.00   58.00    --   -7.70  72.00 -60.00  123
 11  \w    -41.00  29.00   1.00   58.00    --   -7.70  72.00  60.00   70
 12  \w    -38.00  82.00   1.00   58.00    --   -7.70  57.00 -90.00  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      -0.0005571000
_diffrn_orient_matrix_UB_12      0.0908939000
_diffrn_orient_matrix_UB_13      0.0119111000
_diffrn_orient_matrix_UB_21      0.0274659000
_diffrn_orient_matrix_UB_22      -0.0225341000
_diffrn_orient_matrix_UB_23      0.0171279000
_diffrn_orient_matrix_UB_31      0.0128471000
_diffrn_orient_matrix_UB_32      0.0522548000
_diffrn_orient_matrix_UB_33      -0.0133406000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            88531
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.644
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99283
_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    1.160
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0360P)^2^+8.9154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4137
_reflns_number_total             4247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cd1884g.cif
_cod_data_source_block           cd1884g
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_database_code               4133915
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         B2O4C20H15
_chemical_oxdiff_usercomment     HDA9637-12
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Fixed Sof: O4A(0.6) O3A(0.6) C25B(0.6) H25A(0.6) H25B(0.6) H25C(0.6) O3B(0.4)
 O4B(0.4) C25A(0.4) H25D(0.4) H25E(0.4) H25F(0.4)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C6(H6), C9(H9), C5(H5), C10(H10), C13(H13), C12(H12)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C16(H16A,H16B,
 H16C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C),
 C25B(H25A,H25B,H25C), C25A(H25D,H25E,H25F)
;
_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 1.066
_oxdiff_exptl_absorpt_empirical_full_min 0.971