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_4518789
_publ_section_title
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 Development of a Tunable Chiral Pyridine Ligand Unit for Enantioselective
 Iridium-Catalyzed C--H Borylation
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_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 ad
_chemical_formula_moiety         'C20 H18 Cl N O2'
_chemical_formula_sum            'C20 H18 Cl N O2'
_chemical_formula_weight         339.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-10
_audit_creation_method
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Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2846(5)
_cell_length_b                   11.5452(7)
_cell_length_c                   17.4901(10)
_cell_measurement_reflns_used    6320
_cell_measurement_temperature    150
_cell_measurement_theta_max      58.842
_cell_measurement_theta_min      4.589
_cell_volume                     1672.88(17)
_computing_cell_refinement       'SAINT V8.18C (?, 2016)'
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9171
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        58.861
_diffrn_reflns_theta_max         58.861
_diffrn_reflns_theta_min         4.589
_diffrn_source_current           0.65
_diffrn_source_power             0.029133
_diffrn_source_voltage           44.82
_exptl_absorpt_coefficient_mu    2.112
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1176 before and 0.0544 after correction.
The Ratio of minimum to maximum transmission is 0.8163.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.032(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0216
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0249P)^2^+0.1807P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0535
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2305
_reflns_number_total             2378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c01671_si_004.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4518787--4518790.cif.'
_cod_database_code               4518789
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.631
_shelx_estimated_absorpt_t_min   0.589
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.968(15)
 0.032(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C007(H007)
3.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M)
3.c Idealised Me refined as rotating group:
 C00N(H00E,H00L,H00N), C00O(H00O,H00P,H00Q)
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_shelx_res_checksum              51240
_shelx_hkl_checksum              56668
_olex2_submission_special_instructions 'No special instructions were received'
_thetm01_1
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PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
         Calculated sin(theta_max)/wavelength =    0.5551
RESPONSE: This is because diffracted intensity of the single crystal is
weaker. 
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