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_4133924
_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_absolute_configuration ad
_chemical_formula_moiety         'C H Cl3, C31 H37 B O5'
_chemical_formula_sum            'C32 H38 B Cl3 O5'
_chemical_formula_weight         619.78
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2019-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                104.315(2)
_cell_angle_beta                 92.465(2)
_cell_angle_gamma                114.483(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4219(3)
_cell_length_b                   11.3625(3)
_cell_length_c                   16.4678(4)
_cell_measurement_reflns_used    16127
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.4380
_cell_measurement_theta_min      2.5570
_cell_volume                     1533.34(9)
_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 0.998
_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    -97.00  26.00   1.00    7.00    --   -7.70 -72.00  90.00  123
  2  \w    -97.00  18.00   1.00    7.00    --   -7.70 -38.00 150.00  115
  3  \w    -97.00  82.00   1.00    7.00    --   -7.70   0.00-150.00  179
  4  \w    -97.00  82.00   1.00    7.00    --   -7.70   0.00-150.00  179
  5  \w    -41.00  82.00   1.00    7.00    --   -7.70  72.00  30.00  123
  6  \w    -41.00  82.00   1.00    7.00    --   -7.70  72.00 150.00  123
  7  \w    -33.00  82.00   1.00    7.00    --   -7.70  38.00 -60.00  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      -0.0406074000
_diffrn_orient_matrix_UB_12      -0.0417397000
_diffrn_orient_matrix_UB_13      -0.0413842000
_diffrn_orient_matrix_UB_21      -0.0717087000
_diffrn_orient_matrix_UB_22      -0.0246728000
_diffrn_orient_matrix_UB_23      0.0163139000
_diffrn_orient_matrix_UB_31      -0.0155876000
_diffrn_orient_matrix_UB_32      0.0528297000
_diffrn_orient_matrix_UB_33      -0.0072437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43346
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.384
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98067
_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    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_recrystallization_method
'crystallized from slow evaporation of chloroform'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 5290 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     749
_refine_ls_number_reflns         11851
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0500P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.971
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                11638
_reflns_number_total             11851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cd1889.cif
_cod_data_source_block           cd1889
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_original_cell_volume        1533.34(8)
_cod_database_code               4133924
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     HDA825-4
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.868
_reflns_odcompleteness_completeness 99.71
_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.a Ternary CH refined with riding coordinates:
 C13(H13), C36(H36), C43(H43), C5(H5), C44(H44), C12(H12), C65(H65), C64(H64)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B), C14(H14A,H14B), C7(H7A,H7B), C15(H15A,H15B),
 C38(H38A,H38B), C45(H45A,H45B), C37(H37A,H37B), C46(H46A,H46B), C10(H10A,H10B),
  C42(H42A,H42B), C41(H41A,H41B)
2.c Aromatic/amide H refined with riding coordinates:
 C52(H52), C24(H24), C23(H23), C56(H56), C21(H21), C48(H48), C34(H34),
 C20(H20), C33(H33), C2(H2), C53(H53), C55(H55), C17(H17), C3(H3)
2.d Idealised Me refined as rotating group:
 C63(H63A,H63B,H63C), C62(H62A,H62B,H62C), C31(H31A,H31B,H31C), C60(H60A,H60B,
 H60C), C29(H29A,H29B,H29C), C28(H28A,H28B,H28C), C61(H61A,H61B,H61C), C30(H30A,
 H30B,H30C), C27(H27A,H27B,H27C), C59(H59A,H59B,H59C)
;
_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 1.107
_oxdiff_exptl_absorpt_empirical_full_min 0.955