Cu(OTf)<sub>2</sub> catalyzed Ugi-type reaction of <i>N</i>,<i>O</i>-acetals with isocyanides for the synthesis of pyrrolidinyl and piperidinyl 2-carboxamides.
Mao, Zhuo-Ya; Nie, Xiao-Di; Feng, Yi-Man; Si, Chang-Mei; Wei, Bang-Guo; Lin, Guo-Qiang; Chemical communications (Cambridge, England) 57 (2021) 9248–9251; doi:10.1039/d1cc03113a

data_7128861
_publ_section_title
;
 Cu(OTf)<sub>2</sub> catalyzed Ugi-type reaction of
 <i>N</i>,<i>O</i>-acetals with isocyanides for the synthesis of
 pyrrolidinyl and piperidinyl 2-carboxamides.
;
_journal_issue                   73
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9248
_journal_page_last               9251
_journal_paper_doi               10.1039/d1cc03113a
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H15 Br Cl F N2 O'
_chemical_formula_weight         337.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-07-05 deposited with the CCDC.	2021-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.991(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5060(4)
_cell_length_b                   4.7861(3)
_cell_length_c                   21.3358(10)
_cell_measurement_reflns_used    5647
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      55.026
_cell_measurement_theta_min      5.771
_cell_volume                     659.42(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6384
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.886
_exptl_absorpt_coefficient_mu    3.321
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.030(6)
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0195
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0490
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                2373
_reflns_number_total             2446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03113a2.cif
_cod_data_source_block           mo_d8v21544_0m
_cod_depositor_comments
'Adding full bibliography for 7128859--7128864.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7128861
_shelx_estimated_absorpt_t_min   0.602
_shelx_estimated_absorpt_t_max   0.732
_shelxl_version_number           2013-4
_shelx_res_checksum              58929