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_4038672
_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_absolute_configuration unk
_chemical_formula_moiety         'C27 H27 F N2 O3'
_chemical_formula_sum            'C27 H27 F N2 O3'
_chemical_formula_weight         446.5
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0069(3)
_cell_length_b                   14.7854(5)
_cell_length_c                   16.3253(5)
_cell_measurement_reflns_used    9053
_cell_measurement_temperature    120
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      4.03
_cell_volume                     2415.43(13)
_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      120.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0666
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            97609
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.331
_diffrn_reflns_theta_min         4.034
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5203
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1425 before and 0.0876 after correction. The Ratio of minimum to maximum transmission is 0.6909. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_preparation       'as described in manuscript'
_exptl_crystal_recrystallization_method 'as described in manuscript'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         4430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0556P)^2^+0.4188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4343
_reflns_number_total             4430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-163-S2.cif
_cod_data_source_block           cu_20200707b_0m
_cod_depositor_comments
;
Adding full bibliography for 4038672--4038673.cif.

2025-09-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         44.65
_cod_original_formula_moiety         '0.1(C27 H27 F N2 O3)'
_cod_original_formula_units_Z            40
_cod_original_formula_sum        'C2.70 H2.70 F0.10 N0.20 O0.30'
_cod_database_code               4038672
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
;
_shelx_res_checksum              18614
_shelx_hkl_checksum              79513
_olex2_exptl_crystal_mounting_method 'as described in manuscript'
_olex2_submission_special_instructions 'No special instructions were received'