Photocatalytic [3 + 2]-annulation <i>via</i> sodium tetraarylborate: a fundamental approach for synthesizing 1,4,2-diazaborole analogs.
Qin, Hao-Ni; Jiang, Hao-Wen; Zhao, Yi; Qurban, Saira; Wang, Ke-Chun; Xu, Peng-Fei; Chemical science 16 (2025) 2837–2842; doi:10.1039/d4sc08085h

data_1573689
_publ_section_title
;
 Photocatalytic [3 + 2]-annulation <i>via</i> sodium tetraarylborate: a
 fundamental approach for synthesizing 1,4,2-diazaborole analogs.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2837
_journal_page_last               2842
_journal_paper_doi               10.1039/d4sc08085h
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C30 H29 B N2 O3'
_chemical_formula_sum            'C30 H29 B N2 O3'
_chemical_formula_weight         475.85
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-09-04 deposited with the CCDC.	2025-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.7718(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.04999(19)
_cell_length_b                   23.4910(6)
_cell_length_c                   22.4123(4)
_cell_measurement_reflns_used    13467
_cell_measurement_temperature    286(3)
_cell_measurement_theta_max      74.4720
_cell_measurement_theta_min      2.7610
_cell_volume                     5715.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      286(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.949
_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    -82.00 -47.00   0.50    0.90    --  -44.57 109.00  57.00   70
  2  \w     22.00  47.00   0.50    0.90    --   44.57-109.00 -38.00   50
  3  \w   -127.00-100.00   0.50    2.00    -- -100.00-109.00 -38.00   54
  4  \w    -99.00 -29.00   0.50    2.00    -- -100.00 109.00  57.00  140
  5  \w     50.00 108.00   0.50    2.00    --  107.41-109.00 -38.00  116
  6  \w     94.00 145.00   0.50    2.00    --  107.41 109.00  57.00  102
  7  \w    -21.00  22.00   0.50    0.90    --   44.57 -19.00  30.00   86
  8  \w    -13.00  22.00   0.50    0.90    --   44.57 -19.00-120.00   70
  9  \w     -9.00  20.00   0.50    0.90    --   44.57 -19.00 -60.00   58
 10  \w    -33.00  23.00   0.50    0.90    --   44.57 -19.00 -30.00  112
 11  \w    -31.00  32.00   0.50    0.90    --   44.57 -37.00-150.00  126
 12  \w    -30.00  23.00   0.50    0.90    --   44.57 -19.00  90.00  106
 13  \w   -112.00 -49.00   0.50    2.00    -- -100.00 125.00 150.00  126
 14  \w    -54.00 -26.00   0.50    2.00    -- -100.00  45.00-120.00   56
 15  \w    -54.00 -29.00   0.50    2.00    -- -100.00  45.00  60.00   50
 16  \w    -65.00 -33.00   0.50    2.00    -- -100.00  61.00   0.00   64
 17  \w    -54.00 -27.00   0.50    2.00    -- -100.00  45.00 -60.00   54
 18  \w    -92.00 -67.00   0.50    2.00    -- -100.00 125.00  90.00   50
 19  \w    -54.00 -29.00   0.50    2.00    -- -100.00  45.00  30.00   50
 20  \w    -53.00 -25.00   0.50    2.00    -- -100.00  45.00  90.00   56
 21  \w    -54.00 -29.00   0.50    2.00    -- -100.00  45.00   0.00   50
 22  \w    -50.00 -25.00   0.50    2.00    -- -100.00  45.00-180.00   50
 23  \w   -112.00 -27.00   0.50    2.00    -- -100.00 125.00-150.00  170
 24  \w    -52.00 -25.00   0.50    2.00    -- -100.00  45.00-150.00   54
 25  \w   -106.00 -78.00   0.50    2.00    -- -100.00 125.00   0.00   56
 26  \w    -71.00 -26.00   0.50    2.00    -- -100.00 125.00   0.00   90
 27  \w    -54.00 -29.00   0.50    2.00    -- -100.00  45.00 -90.00   50
 28  \w     87.00 136.00   0.50    2.00    --  107.41  45.00-150.00   98
 29  \w     39.00  87.00   0.50    2.00    --  107.41-125.00 -60.00   96
 30  \w     34.00  59.00   0.50    2.00    --  107.41 -61.00 -30.00   50
 31  \w    141.00 175.00   0.50    2.00    --  107.41  45.00-150.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0209260000
_diffrn_orient_matrix_UB_12      0.0634184000
_diffrn_orient_matrix_UB_13      -0.0123700000
_diffrn_orient_matrix_UB_21      0.0403313000
_diffrn_orient_matrix_UB_22      0.0104677000
_diffrn_orient_matrix_UB_23      0.0686983000
_diffrn_orient_matrix_UB_31      0.1344554000
_diffrn_orient_matrix_UB_32      -0.0129944000
_diffrn_orient_matrix_UB_33      -0.0048696000
_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  0.0395
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            43890
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.555
_diffrn_reflns_theta_min         2.751
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             2012
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     663
_refine_ls_number_reflns         11257
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0654P)^2^+0.5202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8288
_reflns_number_total             11257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08085h2.cif
_cod_data_source_block           qinhaoni-xpf_0411_auto
_cod_depositor_comments
;
          Adding full bibliography for 1573689.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C60 H57 B2 N4 O6'
_cod_original_formula_weight         951.71
_cod_original_formula_moiety         '2(C30 H29 B N2 O3)'
_cod_original_formula_units_Z            4
_cod_database_code               1573689
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C59) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C55) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C16(H16), C18(H18), C20(H20), C23(H23), C24(H24),
 C27(H27), C28(H28), C30(H30), C33(H33), C36(H36), C39(H39), C42(H42), C44(H44),
  C47(H47), C48(H48), C49(H49), C51(H51), C21(H21), C25(H25), C26(H26),
 C32(H32), C34(H34), C35(H35), C37(H37), C38(H38), C41(H41), C43(H43), C45(H45),
  C46(H46), C50(H50), C54(H54), C55(H55), C56(H56), C57(H57), C59(H59), C60(H60)
3.b Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C40(H40A,H40B,H40C), C53(H53A,H53B,H53C), C19(H19A,H19B,
 H19C), C52(H52A,H52B,H52C), C58(H58A,H58B,H58C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              52617
_shelx_fab_checksum              41518
_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 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.532