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_7711610
_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         'C25 H19.822 B N'
_chemical_formula_sum            'C25 H19.82 B N'
_chemical_formula_weight         345.05
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-04
_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                90
_cell_angle_beta                 107.445(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.386(4)
_cell_length_b                   8.564(2)
_cell_length_c                   12.291(3)
_cell_measurement_reflns_used    5032
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.797
_cell_measurement_theta_min      2.647
_cell_volume                     1846.3(7)
_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 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0457
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14991
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.647
_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    0.071
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1208 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.8039.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             727
_exptl_crystal_preparation       diffusion
_exptl_crystal_recrystallization_method diffusion
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     210
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0579P)^2^+1.9580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2647
_reflns_number_total             3173
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt03303h2.cif
_cod_data_source_block           220525_ysg_hashizume_02_0ma_a
_cod_database_code               7711610
_shelx_shelxl_version_number     2018/3
_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. Uiso/Uaniso restraints and constraints
Uanis(C0) \\sim Ueq, Uanis(N0) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 C007, C00H, C00L, C00K, C00C, C008
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C0, B00Q, C1, C2, N0
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C0, C003, C004, C00I, C00O, C00N
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 B00Q, C0, C1, N0, C2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C001, C009, C00A, C00G, C00E, C00B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N0, C00B, C00E, C00G, C00A, C009
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C005, C00J, C00M, C00D, C00F, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2, C008, C00C, C00K, C00L, C00H
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H00A)=Sof(H00G)=Sof(H00H)=Sof(N0)=Sof(C0)=Sof(H00R)=Sof(C1)=Sof(C2)=
 Sof(H00X)=Sof(C3)=Sof(H3A)=Sof(H3B)=1-FVAR(1)
 Sof(C001)=Sof(H00B)=Sof(N002)=Sof(C006)=Sof(H00F)=Sof(C007)=Sof(C00R)=
 Sof(H00N)=Sof(H00O)=Sof(H00P)=Sof(H00Q)=Sof(H00U)=Sof(H00W)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00B(H00A), C00E(H00E), C00G(H00G), C00A(H00C), C00J(H00J),
 C00M(H00M), C00D(H00D), C00F(H00F), C00F(H00H), C00N(H00Q), C00N(H00R),
 C00O(H00S), C004(H004), C00C(H00T), C00K(H00U), C00L(H00V), C00H(H00W),
 C00H(H00X)
5.b Fitted hexagon refined as free rotating group:
 C001(C00B,C00E,C00G,C00A,C009), C006(C005,C00J,C00M,C00D,C00F), C0(C00N,C00O,
 C00I,C004,C003), C2(C008,C00C,C00K,C00L,C00H)
5.c X=CH2 refined with riding coordinates:
 C3(H3A,H3B)
5.d Idealised Me refined as rotating group:
 C00P(H00I,H00K,H00L), C00R(H00N,H00O,H00P)
;
_shelx_res_checksum              15359
_olex2_exptl_crystal_mounting_method cryoroop
_olex2_submission_special_instructions 'No special instructions were received'