Development of a Tunable Chiral Pyridine Ligand Unit for Enantioselective Iridium-Catalyzed C‒H Borylation
Song, Peidong; Hu, Linlin; Yu, Tao; Jiao, Jiao; He, Yangqing; Xu, Liang; Li, Pengfei; ACS Catalysis 11 (2021) 7339–7349; doi:10.1021/acscatal.1c01671

data_4518787
_publ_section_title
;
 Development of a Tunable Chiral Pyridine Ligand Unit for Enantioselective
 Iridium-Catalyzed C--H Borylation
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              7339
_journal_page_last               7349
_journal_paper_doi               10.1021/acscatal.1c01671
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H14 B F2 N'
_chemical_formula_sum            'C18 H14 B F2 N'
_chemical_formula_weight         293.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-09-22
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.980(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.347(3)
_cell_length_b                   7.9177(16)
_cell_length_c                   13.683(3)
_cell_measurement_reflns_used    6625
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.332
_cell_measurement_theta_min      2.973
_cell_volume                     1445.1(5)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution
'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_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            15057
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.521
_diffrn_reflns_theta_min         1.489
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0513 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.8858.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5837
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0299P)^2^+0.7876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5183
_reflns_number_total             5837
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01671_si_005.cif
_cod_data_source_block           mo_spd20200819_0m
_cod_depositor_comments
'Adding full bibliography for 4518787--4518790.cif.'
_cod_original_cell_volume        1445.2(5)
_cod_database_code               4518787
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B), C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015), C016(H016)
;
_shelx_res_checksum              38974
_shelx_hkl_checksum              99545
_olex2_submission_special_instructions 'No special instructions were received'