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_7245348
_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_absolute_configuration unk
_chemical_formula_moiety         'C15 H20 B N3 O'
_chemical_formula_sum            'C15 H20 B N3 O'
_chemical_formula_weight         269.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-02-13 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2427(5)
_cell_length_b                   7.8871(6)
_cell_length_c                   29.178(2)
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2160
_cell_measurement_theta_min      5.8180
_cell_volume                     1436.63(19)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.995
_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    -86.00  -4.00   1.00    2.99    --  -35.75 -17.00-127.00   82
  2  \w    -73.00 -41.00   1.00    2.99    --  -35.75 109.00-179.00   32
  3  \w    100.00 143.00   1.00   11.97    --  107.12 109.00-179.00   43
  4  \w     40.00  66.00   1.00   11.97    --  107.12 -17.00-127.00   26
  5  \w     42.00  91.00   1.00   11.97    --  107.12-132.00-171.00   49
  6  \w     64.00 108.00   1.00    2.99    --   35.75 178.00-150.00   44
  7  \w     43.00  99.00   1.00    2.99    --   35.75  57.00-120.00   56
  8  \w     77.00 111.00   1.00   11.97    --  107.12-111.00  60.00   34
  9  \w     39.00 117.00   1.00   11.97    --  107.12 -30.00 -90.00   78
 10  \w     42.00 121.00   1.00   11.97    --  107.12 -61.00-180.00   79
;
_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      0.0376419000
_diffrn_orient_matrix_UB_12      -0.1300647000
_diffrn_orient_matrix_UB_13      0.0385791000
_diffrn_orient_matrix_UB_21      -0.0340447000
_diffrn_orient_matrix_UB_22      0.1401129000
_diffrn_orient_matrix_UB_23      0.0360974000
_diffrn_orient_matrix_UB_31      -0.2413904000
_diffrn_orient_matrix_UB_32      -0.0399652000
_diffrn_orient_matrix_UB_33      0.0008880000
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            3502
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.537
_diffrn_reflns_theta_min         5.811
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88467
_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    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0255P)^2^+0.9137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                1869
_reflns_number_total             2428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02313j2.cif
_cod_data_source_block           myq
_cod_depositor_comments
'Adding full bibliography for 7245347--7245349.cif.'
_cod_original_cell_volume        1436.64(19)
_cod_database_code               7245348
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 O1 N1 B1 '
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.994
_reflns_odcompleteness_completeness 99.42
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C8(H8), C14(H14), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              40670
_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 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.642