Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination.
Wang, Yuqing; Wang, Gaigai; Peshkov, Anatoly A.; Yao, Ruwei; Hasan, Muhammad; Zaman, Manzoor; Liu, Chao; Kashtanov, Stepan; Pereshivko, Olga P.; Peshkov, Vsevolod A.; Beilstein journal of organic chemistry 16 (2020) 1963–1973; doi:10.3762/bjoc.16.163

data_4038673
_publ_section_title
;
 Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts
 through the cinchona alkaloid-promoted electrophilic fluorination.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1963
_journal_page_last               1973
_journal_paper_doi               10.3762/bjoc.16.163
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C27 H27 F N2 O3'
_chemical_formula_sum            'C27 H27 F N2 O3'
_chemical_formula_weight         446.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.560(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.199(2)
_cell_length_b                   11.712(2)
_cell_length_c                   15.424(3)
_cell_measurement_reflns_used    9433
_cell_measurement_temperature    120
_cell_measurement_theta_max      68.412
_cell_measurement_theta_min      5.048
_cell_volume                     2383.5(7)
_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      120.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 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  0.1095
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31661
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.782
_diffrn_reflns_theta_min         4.741
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4852
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1500 before and 0.1041 after correction. The Ratio of minimum to maximum transmission is 0.6443. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_preparation       'as in described in manuscript'
_exptl_crystal_recrystallization_method 'as described in manuscript'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0795P)^2^+2.5883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1783
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3420
_reflns_number_total             4366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-163-S3.cif
_cod_data_source_block           cu_b200702a_0ma_pl_pl
_cod_depositor_comments
'Adding full bibliography for 4038672--4038673.cif.'
_cod_database_code               4038673
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
;
_shelx_res_checksum              94749
_shelx_hkl_checksum              80762
_olex2_exptl_crystal_mounting_method 'as described in manuscript'
_olex2_submission_original_sample_id wyq-56
_olex2_submission_special_instructions 'No special instructions were received'