Synthesis and stereochemistry of chiral aza-boraspirobifluorenes with tetrahedral boron-stereogenic centers
Yoshigoe, Yusuke; Hashizume, Keiichiro; Saito, Shinichi; Dalton Transactions  (2022) –; doi:10.1039/D2DT03303H

data_7711606
_publ_section_title
;
 Synthesis and stereochemistry of chiral aza-boraspirobifluorenes with
 tetrahedral boron-stereogenic centers
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT03303H
_journal_year                    2022
_chemical_formula_moiety         'C24 H18 B N O'
_chemical_formula_sum            'C24 H18 B N O'
_chemical_formula_weight         347.20
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                109.1900(10)
_cell_angle_beta                 103.359(2)
_cell_angle_gamma                108.8850(10)
_cell_formula_units_Z            4
_cell_length_a                   11.9380(5)
_cell_length_b                   12.7143(5)
_cell_length_c                   14.2807(6)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      31.03
_cell_measurement_theta_min      2.55
_cell_volume                     1793.52(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.780
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1616
_diffrn_reflns_av_unetI/netI     0.1262
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.780
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41838
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.481
_diffrn_reflns_theta_min         1.875
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6960
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.349
_exptl_crystal_size_min          0.258
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         9289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0808P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6084
_reflns_number_total             9289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03303h2.cif
_cod_data_source_block           211006_ysg_hashizume_02_0m_a
_cod_depositor_comments
;

2024-11-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H36 B2 N2 O2'
_cod_original_formula_weight         694.41
_cod_original_formula_moiety         '2(C24 H18 B N O)'
_cod_original_formula_units_Z            2
_cod_database_code               7711606
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.957
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C30(H30), C33(H33), C34(H34), C38(H38), C41(H41),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              10370
_olex2_submission_special_instructions 'No special instructions were received'