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_7245347
_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         'C20 H33 B N2 S'
_chemical_formula_sum            'C20 H33 B N2 S'
_chemical_formula_weight         344.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-24
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-02-13 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.570(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8039(2)
_cell_length_b                   17.1774(4)
_cell_length_c                   14.8916(3)
_cell_measurement_reflns_used    6364
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.6940
_cell_measurement_theta_min      5.1530
_cell_volume                     1995.48(8)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_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    -90.00 -54.00   1.00    1.00    --  -35.62 128.00 164.00   36
  2  \w    -55.00 -12.00   1.00    1.00    --  -35.62 143.00 -25.00   43
  3  \w     42.00  90.00   1.00    1.00    --   35.62-128.00  89.00   48
  4  \w    106.00 164.00   1.00    1.00    --  107.12 128.00 164.00   58
  5  \w    105.00 130.00   1.00    1.00    --  107.12 143.00 -25.00   25
  6  \w     55.00  80.00   1.00    1.00    --  107.12-128.00  89.00   25
  7  \w     46.00 130.00   1.00    1.00    --  107.12-143.00 -80.00   84
  8  \w   -101.00 -20.00   1.00    1.00    --  -35.62 -57.00 -90.00   81
  9  \w    -30.00  34.00   1.00    1.00    --   35.62 -57.00-180.00   64
 10  \w     19.00 104.00   1.00    1.00    --   35.62  38.00  30.00   85
 11  \w     38.00 129.00   1.00    1.00    --  107.12 -30.00-180.00   91
 12  \w    107.00 134.00   1.00    1.00    --  107.12 111.00 150.00   27
 13  \w    101.00 153.00   1.00    1.00    --  107.12 111.00-150.00   52
 14  \w     63.00 110.00   1.00    1.00    --  107.12 -95.00  60.00   47
 15  \w     90.00 174.00   1.00    1.00    --  107.12  30.00   0.00   84
 16  \w     41.00 130.00   1.00    1.00    --  107.12 -77.00-120.00   89
 17  \w     39.00 117.00   1.00    1.00    --  107.12 -30.00  30.00   78
;
_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      0.0450092000
_diffrn_orient_matrix_UB_12      0.0537548000
_diffrn_orient_matrix_UB_13      -0.0787818000
_diffrn_orient_matrix_UB_21      0.0211535000
_diffrn_orient_matrix_UB_22      -0.0715695000
_diffrn_orient_matrix_UB_23      -0.0610027000
_diffrn_orient_matrix_UB_31      -0.1910846000
_diffrn_orient_matrix_UB_32      0.0047488000
_diffrn_orient_matrix_UB_33      -0.0282573000
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.440
_diffrn_reflns_theta_min         3.930
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56261
_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    1.146
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0545P)^2^+2.4705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3580
_reflns_number_total             3794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02313j2.cif
_cod_data_source_block           20211224-myq
_cod_depositor_comments
'Adding full bibliography for 7245347--7245349.cif.'
_cod_database_code               7245347
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 N1 S1 B1'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C19(H19), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 B8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C15(H15A,H15B,
 H15C), C20(H20A,H20B,H20C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C17(H17A,
 H17B,H17C)
;
_shelx_res_checksum              25514
_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 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.588