Rhodium-catalyzed annulative approach to N-N axially chiral biaryls <i>via</i> C-H activation and dynamic kinetic transformation.
Zhu, Xiaohan; Wu, Hongli; Wang, Yishou; Huang, Genping; Wang, Fen; Li, Xingwei; Chemical science 14 (2023) 8564–8569; doi:10.1039/d3sc02800c

data_1569538
_publ_section_title
;
 Rhodium-catalyzed annulative approach to N-N axially chiral biaryls
 <i>via</i> C-H activation and dynamic kinetic transformation.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              8564
_journal_page_last               8569
_journal_paper_doi               10.1039/d3sc02800c
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H22 N2 O'
_chemical_formula_sum            'C30 H22 N2 O'
_chemical_formula_weight         426.49
_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             2022-10-07
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5313(3)
_cell_length_b                   14.4824(5)
_cell_length_c                   16.6299(5)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    180.00
_cell_measurement_theta_max      68.249
_cell_measurement_theta_min      2.657
_cell_volume                     2295.53(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      180.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34480
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.280
_diffrn_reflns_theta_min         4.048
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1140 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.8948.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1718 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     93
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0378P)^2^+0.2602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4037
_reflns_number_total             4169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02800c3.cif
_cod_data_source_block           s
_cod_depositor_comments          'Adding full bibliography for 1569538.cif.'
_cod_database_code               1569538
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C22(H22), C24(H24), C26(H26), C28(H28), C30(H30), C2(H2),
 C17(H17), C9(H9), C19(H19), C5(H5), C23(H23), C3(H3), C25(H25), C13(H13),
 C27(H27), C7(H7), C29(H29)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              44692
_olex2_submission_special_instructions 'No special instructions were received'