Triborane (B<sub>3</sub>H<sub>7</sub>)-mediated regioselective substitution reactions of pyridine derivatives.
Fan, Zi-Heng; Kang, Jia-Xin; Jia, Sihan; Pan, Qiao-Jing; Cao, Lei; Chen, Xi-Meng; Xu, Cong-Qiao; Ma, Yan-Na; Chen, Xuenian; Chemical science 15 (2024) 13923–13929; doi:10.1039/d4sc03109a

data_1572201
_publ_section_title
;
 Triborane (B<sub>3</sub>H<sub>7</sub>)-mediated regioselective
 substitution reactions of pyridine derivatives.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              13923
_journal_page_last               13929
_journal_paper_doi               10.1039/d4sc03109a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C5 H12 B3 N'
_chemical_formula_sum            'C5 H12 B3 N'
_chemical_formula_weight         118.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-15 deposited with the CCDC.	2024-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9099(8)
_cell_length_b                   8.0101(4)
_cell_length_c                   14.4607(8)
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6820
_cell_measurement_theta_min      6.3670
_cell_volume                     1611.21(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.953
_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   -102.00 -44.00   1.00    1.51    --  -35.62 -57.00 -42.00   58
  2  \w      4.00  33.00   1.00    1.51    --   35.62 -96.00  87.00   29
  3  \w      4.00  45.00   1.00    1.51    --   35.62 -73.00-177.00   41
  4  \w    110.00 168.00   1.00    6.03    --  106.81  73.00 -48.00   58
  5  \w    111.00 165.00   1.00    6.03    --  106.81  57.00  98.00   54
  6  \w     40.00 104.00   1.00    6.03    --  106.81 -57.00 -42.00   64
  7  \w     41.00 101.00   1.00    6.03    --  106.81 -96.00  87.00   60
  8  \w     64.00  94.00   1.00    1.51    --   35.62 178.00   0.00   30
  9  \w     58.00 108.00   1.00    1.51    --   35.62-178.00-150.00   50
 10  \w     66.00 105.00   1.00    1.51    --   35.62 178.00  90.00   39
 11  \w    108.00 157.00   1.00    6.03    --  106.81  77.00  60.00   49
 12  \w     53.00 105.00   1.00    6.03    --  106.81-111.00-150.00   52
 13  \w    127.00 173.00   1.00    6.03    --  106.81 111.00 -90.00   46
;
_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      0.0672201000
_diffrn_orient_matrix_UB_12      -0.1410068000
_diffrn_orient_matrix_UB_13      0.0327000000
_diffrn_orient_matrix_UB_21      0.0349498000
_diffrn_orient_matrix_UB_22      0.1106990000
_diffrn_orient_matrix_UB_23      0.0805265000
_diffrn_orient_matrix_UB_31      -0.0809223000
_diffrn_orient_matrix_UB_32      -0.0689226000
_diffrn_orient_matrix_UB_33      0.0617386000
_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  0.0182
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4012
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.205
_diffrn_reflns_theta_min         6.121
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    0.978
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0724P)^2^+0.3844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1154
_reflns_number_total             1486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03109a2.cif
_cod_data_source_block           20231010-fzh_auto
_cod_depositor_comments
'Adding full bibliography for 1572200--1572201.cif.'
_cod_database_code               1572201
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 N1 B1 H1'
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.996
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C4(H4)
;
_smtbx_masks_void_probe_radius   0.5
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              16497
_shelx_hkl_checksum              80512
_shelx_fab_checksum              80489
_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 1.257
_oxdiff_exptl_absorpt_empirical_full_min 0.667