NHC catalyzed radical tandem cyclization: an efficient synthesis of α,α-difluoro-γ-lactam derivatives.
Huang, Tianjiao; Yin, Huiping; Li, Tuanjie; Yu, Chenxia; Zhang, Kai; Yao, Changsheng; Organic & biomolecular chemistry 22 (2024) 6988–6998; doi:10.1039/d4ob01012d

data_7160086
_publ_section_title
;
 NHC catalyzed radical tandem cyclization: an efficient synthesis of
 &#x3b1;,&#x3b1;-difluoro-&#x3b3;-lactam derivatives.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6988
_journal_page_last               6998
_journal_paper_doi               10.1039/d4ob01012d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C25 H20 Br F2 N O2'
_chemical_formula_sum            'C25 H20 Br F2 N O2'
_chemical_formula_weight         484.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-05-24 deposited with the CCDC.	2024-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.338(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7990(13)
_cell_length_b                   25.874(4)
_cell_length_c                   10.0568(14)
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.913
_cell_measurement_theta_min      2.225
_cell_volume                     2227.8(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            54833
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.629
_diffrn_reflns_theta_min         2.506
_exptl_absorpt_coefficient_mu    1.883
_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    1.444
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0632
_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^)+(0.0747P)^2^+1.9866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1815
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3861
_reflns_number_total             5663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01012d2.cif
_cod_data_source_block           3aa-2
_cod_depositor_comments
'Adding full bibliography for 7160085--7160086.cif.'
_cod_database_code               7160086
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
;
_olex2_submission_special_instructions 'No special instructions were received'