Organocatalytic enantioselective synthesis of C<sub>sp<sub>2</sub></sub>-N atropisomers <i>via</i> formal C<sub>sp<sub>2</sub></sub>-O bond amination.
Qian, Chenxiao; Huang, Jing; Huang, Tingting; Song, Lijuan; Sun, Jianwei; Li, Pengfei; Chemical science 15 (2024) 3893–3900; doi:10.1039/d3sc06707f

data_1570971
_publ_section_title
;
 Organocatalytic enantioselective synthesis of
 C<sub>sp<sub>2</sub></sub>-N atropisomers <i>via</i> formal
 C<sub>sp<sub>2</sub></sub>-O bond amination.
;
_journal_issue                   11
_journal_name_full               'Chemical science'
_journal_page_first              3893
_journal_page_last               3900
_journal_paper_doi               10.1039/d3sc06707f
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H19 N O2'
_chemical_formula_sum            'C27 H19 N O2'
_chemical_formula_weight         389.43
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                72.435(2)
_cell_angle_beta                 82.536(2)
_cell_angle_gamma                83.621(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8226(5)
_cell_length_b                   9.8700(6)
_cell_length_c                   13.4677(8)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      74.72
_cell_measurement_theta_min      3.46
_cell_volume                     980.10(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38301
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.726
_diffrn_reflns_theta_min         3.460
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0855 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.9146. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 3501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_coef       0.0114(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7748
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0459P)^2^+0.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0797
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                7449
_reflns_number_total             7748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06707f2.cif
_cod_data_source_block           cxy1938_0m
_cod_depositor_comments
'Adding full bibliography for 1570969--1570971.cif.'
_cod_database_code               1570971
_shelx_shelxl_version_number     2019/2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C23(H23), C27(H27), C7(H7), C11(H11), C17(H17), C22(H22), C25(H25),
 C16(H16), C14(H14), C15(H15), C24(H24), C8(H8), C26(H26), C10(H10), C9(H9),
 C51(H51), C50(H50), C35(H35), C38(H38), C37(H37), C39(H39), C45(H45), C42(H42),
  C36(H36), C32(H32), C43(H43), C52(H52), C55(H55), C44(H44), C54(H54), C53(H53)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C56(H56A,H56B,H56C)
;
_shelx_res_checksum              51214
_olex2_submission_special_instructions 'No special instructions were received'