Copper-catalyzed [3+1] cyclization of cyclopropenes/diazo compounds and bromodifluoroacetamides: facile synthesis of α,α-difluoro-β-lactam derivatives
Zhang, Mengru; Li, Hexin; Zhao, Jinbo; Li, Yan; Zhang, Qian; Chemical Science  (2021) –; doi:10.1039/D1SC02930D

data_1564276
_publ_section_title
;
 Copper-catalyzed [3+1] cyclization of cyclopropenes/diazo compounds and
 bromodifluoroacetamides: facile synthesis of \a,\a-difluoro-\b-lactam
 derivatives
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02930D
_journal_year                    2021
_chemical_formula_moiety         'C18 H14 Cl F2 N O'
_chemical_formula_sum            'C18 H14 Cl F2 N O'
_chemical_formula_weight         333.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2019-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-09 deposited with the CCDC.	2021-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                70.47(3)
_cell_angle_beta                 79.17(4)
_cell_angle_gamma                66.85(3)
_cell_formula_units_Z            4
_cell_length_a                   10.946(7)
_cell_length_b                   11.711(6)
_cell_length_c                   14.387(8)
_cell_measurement_reflns_used    4067
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      63.16
_cell_measurement_theta_min      4.29
_cell_volume                     1594.8(16)
_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      292.73
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14956
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.273
_diffrn_reflns_theta_min         3.266
_exptl_absorpt_coefficient_mu    2.343
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.0826
_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^)+(0.0922P)^2^+1.2857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.2199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3203
_reflns_number_total             5599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02930d2.cif
_cod_data_source_block           ss
_cod_original_cell_volume        1594.9(16)
_cod_database_code               1564276
_shelx_shelxl_version_number     2014/7
_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 Ternary CH refined with riding coordinates:
 C27(H27), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C36(H36), C3(H3), C23(H23), C14(H14), C28(H28), C10(H10), C2(H2), C1(H1),
 C5(H5), C21(H21), C24(H24), C32(H32), C33(H33), C34(H34), C6(H6), C19(H19),
 C18(H18), C20(H20), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              78192
_shelx_hkl_checksum              65993
_olex2_submission_special_instructions 'No special instructions were received'