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_4518790
_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_formula_moiety         'C11 H11 Cl N O2'
_chemical_formula_sum            'C11 H11 Cl N O2'
_chemical_formula_weight         224.67
_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             2020-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.132(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.738(3)
_cell_length_b                   11.313(4)
_cell_length_c                   11.517(4)
_cell_measurement_reflns_used    3792
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.525
_cell_measurement_theta_min      2.529
_cell_volume                     1004.2(6)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.544
_diffrn_reflns_theta_min         2.529
_exptl_absorpt_coefficient_mu    0.357
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0617P)^2^+1.0543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1715
_reflns_number_total             2083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01671_si_003.cif
_cod_data_source_block           1
_cod_depositor_comments
;
Adding full bibliography for 4518787--4518790.cif.

2025-09-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C3.67 H3.67 Cl0.33 N0.33 O0.67'
_cod_original_formula_weight         74.89
_cod_original_formula_moiety         '0.33(C11 H11 Cl N O2)'
_cod_original_formula_units_Z            12
_cod_original_cell_volume        1004.1(6)
_cod_database_code               4518790
_shelx_shelxl_version_number     2014/7
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_shelx_res_checksum              52625
_shelx_hkl_checksum              97736
_olex2_submission_special_instructions 'No special instructions were received'