Enantioselective palladium-catalyzed C–H functionalization of pyrroles using an axially chiral 2,2′-bipyridine ligand
Shen, Hong-Qiang; Liu, Cong; Zhou, Ji; Zhou, Yong-Gui; Organic Chemistry Frontiers 5 (2018) 611–; doi:10.1039/C7QO00815E

data_1553906
_publ_section_title
;
 Enantioselective palladium-catalyzed C--H functionalization of pyrroles
 using an axially chiral 2,2&#x2032;-bipyridine ligand
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              611
_journal_paper_doi               10.1039/C7QO00815E
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C23 H25 N O2'
_chemical_formula_sum            'C23 H25 N O2'
_chemical_formula_weight         347.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-08-04 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.034(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0278(9)
_cell_length_b                   8.4534(5)
_cell_length_c                   14.6680(8)
_cell_measurement_reflns_used    8702
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      70.11
_cell_measurement_theta_min      5.360
_cell_volume                     1983.59(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      301.2
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13417
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.161
_diffrn_reflns_theta_min         5.359
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1466 before and 0.0857 after correction. The Ratio of minimum to maximum transmission is 0.7033. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0640
_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^)+(0.1124P)^2^+0.3301P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1844
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                3230
_reflns_number_total             3654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00815e2.cif
_cod_data_source_block           cu_d8v17020_0m
_cod_database_code               1553906
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.846
_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.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              25593
_shelx_hkl_checksum              18152
_olex2_submission_special_instructions 'No special instructions were received'