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_1570970
_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_formula_moiety         'C27 H19 N O2, C1.5 H3 O0.5'
_chemical_formula_sum            'C28.5 H22 N O2.5'
_chemical_formula_weight         418.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-20
_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                90
_cell_angle_beta                 124.150(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.218(2)
_cell_length_b                   10.8756(7)
_cell_length_c                   17.0557(12)
_cell_measurement_reflns_used    8495
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.39
_cell_volume                     4331.7(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.222
_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    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1525 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.9194.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0508P)^2^+3.6210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             4998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06707f2.cif
_cod_data_source_block           cxy1959_0m
_cod_depositor_comments
'Adding full bibliography for 1570969--1570971.cif.'
_cod_original_formula_sum        'C28.50 H22 N O2.50'
_cod_database_code               1570970
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C24(H24), C23(H23), C14(H14), C26(H26), C17(H17), C27(H27), C5(H5),
 C20(H20), C25(H25), C8(H8), C6(H6), C7(H7), C19(H19), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              81840
_olex2_submission_special_instructions 'No special instructions were received'