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_7711609
_publ_section_title
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 Synthesis and stereochemistry of chiral aza-boraspirobifluorenes with
 tetrahedral boron-stereogenic centers
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_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT03303H
_journal_year                    2022
_chemical_formula_moiety         'C25 H17 B F3 N'
_chemical_formula_sum            'C25 H17 B F3 N'
_chemical_formula_weight         399.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-08-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-24 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.678(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5923(5)
_cell_length_b                   10.4752(6)
_cell_length_c                   21.9452(12)
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.834
_cell_measurement_theta_min      3.06
_cell_volume                     1974.35(19)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_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      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0513
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         1.857
_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    0.097
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1110 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.9172.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_preparation       diffusion
_exptl_crystal_recrystallization_method diffusion
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.018(2)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     165
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0442P)^2^+0.7989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3083
_reflns_number_total             3754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03303h2.cif
_cod_data_source_block           220525_ysg_hashizume_01_0m_a
_cod_database_code               7711609
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.997
_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. Restrained distances
 F2-F1 \\sim F2-F3 \\sim F1-F3 \\sim F2A-F3A \\sim F2A-F1A \\sim F3A-F1A
 with sigma of 0.04
 C9-C8 \\sim C9-F2 \\sim C9-F1 \\sim C9-F3 \\sim C9-F2A \\sim C9-F3A \\sim
C9-F1A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F3A, F1A, F2A, C9, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, F1, F3, C9, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C15, C20, C18, C17, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5, C14, C13, C2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(F2A)=Sof(F3A)=Sof(F1A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(1)
 Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(C5A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C16A)=Sof(C15A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C5)=Sof(C14)=Sof(C13)=Sof(H13)=Sof(C2)=
 Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=
 Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C15)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C4(H4), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C4A(H4A), C3A(H3A),
  C13A(H13A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A)
5.b Fitted hexagon refined as free rotating group:
 C5(C14,C13,C2,C3,C4), C16(C17,C18,C19,C20,C15)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              57654
_olex2_exptl_crystal_mounting_method cryoroop
_olex2_submission_special_instructions 'No special instructions were received'