A general photo-induced wide-scope regioselective hydroboration of alkenes without using a photocatalyst or an external initiator
Miao, Yu-Qi; Li, Xin-Ying; Pan, Qiao-Jing; Ma, Yubin; Kang, Jia-Xin; Ma, Yan-Na; Liu, Zhenxing; Chen, Xuenian; Green Chemistry 24 (2022) 7113–7121; doi:10.1039/D2GC02313J

data_7245349
_publ_section_title
;
 A general photo-induced wide-scope regioselective hydroboration of
 alkenes without using a photocatalyst or an external initiator
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              7113
_journal_page_last               7121
_journal_paper_doi               10.1039/D2GC02313J
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C16 H21 B N2 O2'
_chemical_formula_sum            'C16 H21 B N2 O2'
_chemical_formula_weight         284.16
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-11-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-13 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                114.228(8)
_cell_angle_beta                 106.840(6)
_cell_angle_gamma                93.503(6)
_cell_formula_units_Z            2
_cell_length_a                   9.0836(6)
_cell_length_b                   9.1558(8)
_cell_length_c                   11.0863(8)
_cell_measurement_reflns_used    2568
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3540
_cell_measurement_theta_min      5.1990
_cell_volume                     787.46(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_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    -15.00  25.00   1.00    1.00    --  -35.75  57.00 168.00   40
  2  \w    -99.00 -55.00   1.00    1.00    --  -35.75 -57.00  26.00   44
  3  \w     21.00  83.00   1.00    1.00    --   35.75  57.00 168.00   62
  4  \w      9.00  35.00   1.00    1.00    --   35.75 -57.00  26.00   26
  5  \w    123.00 173.00   1.00    2.19    --  107.12  57.00 168.00   50
  6  \w     57.00  84.00   1.00    2.19    --  107.12 -57.00  26.00   27
  7  \w   -108.00 -37.00   1.00    1.00    --  -35.75-178.00 -30.00   71
  8  \w     37.00  70.00   1.00    1.00    --   35.75 -99.00-180.00   33
  9  \w     22.00  75.00   1.00    1.00    --   35.75 -99.00 -30.00   53
 10  \w      6.00 107.00   1.00    1.00    --   35.75  19.00  30.00  101
 11  \w     20.00 103.00   1.00    1.00    --   35.75  57.00 -90.00   83
 12  \w     58.00 107.00   1.00    1.00    --   35.75 178.00 -30.00   49
 13  \w    104.00 148.00   1.00    2.19    --  107.12  61.00 150.00   44
 14  \w     39.00 125.00   1.00    2.19    --  107.12 -45.00  60.00   86
 15  \w     58.00 149.00   1.00    2.19    --  107.12 178.00 -60.00   91
 16  \w     62.00  88.00   1.00    2.19    --  107.12 -95.00  60.00   26
 17  \w     51.00 110.00   1.00    2.19    --  107.12-111.00 -30.00   59
 18  \w     52.00 109.00   1.00    2.19    --  107.12 -95.00   0.00   57
 19  \w     55.00  89.00   1.00    2.19    --  107.12 -95.00-120.00   34
 20  \w     40.00 124.00   1.00    2.19    --  107.12 -45.00 -60.00   84
 21  \w     92.00 149.00   1.00    2.19    --  107.12  45.00 -60.00   57
 22  \w     61.00 113.00   1.00    2.19    --  107.12-111.00 150.00   52
 23  \w     81.00 122.00   1.00    2.19    --  107.12  77.00-150.00   41
 24  \w     90.00 161.00   1.00    2.19    --  107.12  30.00  90.00   71
 25  \w    113.00 151.00   1.00    2.19    --  107.12 111.00  90.00   38
 26  \w    106.00 160.00   1.00    2.19    --  107.12 111.00  30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0750863000
_diffrn_orient_matrix_UB_12      -0.1441454000
_diffrn_orient_matrix_UB_13      0.0151414000
_diffrn_orient_matrix_UB_21      0.0619577000
_diffrn_orient_matrix_UB_22      -0.1192512000
_diffrn_orient_matrix_UB_23      -0.1098749000
_diffrn_orient_matrix_UB_31      0.1526954000
_diffrn_orient_matrix_UB_32      0.0236170000
_diffrn_orient_matrix_UB_33      0.1186285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5210
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.566
_diffrn_reflns_theta_min         4.662
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0668P)^2^+0.2016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             2990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02313j2.cif
_cod_data_source_block           20210628-myq
_cod_depositor_comments
'Adding full bibliography for 7245347--7245349.cif.'
_cod_original_cell_volume        787.46(12)
_cod_database_code               7245349
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 B1 O1'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C20(H20a,H20b,H20c), C18(H18a,H18b,H18c), C17(H17a,H17b,
 H17c)
;
_shelx_res_checksum              59021
_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.673