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_4133920
_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         'C18 H22 I N O4'
_chemical_formula_sum            'C18 H22 I N O4'
_chemical_formula_weight         443.26
_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             2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.458(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7645(4)
_cell_length_b                   7.7901(2)
_cell_length_c                   16.2371(4)
_cell_measurement_reflns_used    28664
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.9500
_cell_measurement_theta_min      2.5740
_cell_volume                     1781.52(8)
_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    -85.00  39.00   1.00    4.08    --    4.20 -23.00  91.00  124
  2  \w    -42.00  82.00   1.00    4.08    --   -7.70  23.00-103.00  124
  3  \w    -97.00  23.00   1.00    4.08    --   -7.70 -57.00-180.00  120
  4  \w    -97.00  18.00   1.00    4.08    --   -7.70 -38.00 -90.00  115
  5  \w    -38.00  82.00   1.00    4.08    --   -7.70  57.00 120.00  120
  6  \w    -38.00  82.00   1.00    4.08    --   -7.70  57.00 -60.00  120
  7  \w    -97.00  23.00   1.00    4.08    --   -7.70 -57.00   0.00  120
  8  \w    -38.00  82.00   1.00    4.08    --   -7.70  57.00   0.00  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      0.0373614000
_diffrn_orient_matrix_UB_12      0.0041195000
_diffrn_orient_matrix_UB_13      -0.0190312000
_diffrn_orient_matrix_UB_21      0.0326957000
_diffrn_orient_matrix_UB_22      -0.0271158000
_diffrn_orient_matrix_UB_23      0.0394984000
_diffrn_orient_matrix_UB_31      -0.0084584000
_diffrn_orient_matrix_UB_32      -0.0868050000
_diffrn_orient_matrix_UB_33      -0.0132499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46440
_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         25.490
_diffrn_reflns_theta_min         2.593
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90146
_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    1.653
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.33
_refine_diff_density_max         1.175
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0550P)^2^+4.5126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3312
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cd1921c.cif
_cod_data_source_block           cd1921c
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_database_code               4133920
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C17H22O2N1I
_chemical_oxdiff_usercomment     'Larianov NMR sample :)'
_shelx_estimated_absorpt_t_max   0.585
_shelx_estimated_absorpt_t_min   0.463
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C17(H17A,H17B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C)
;
_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 1.132
_oxdiff_exptl_absorpt_empirical_full_min 0.902