Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines
Fu, Yiwei; Shi, Haoyu; Lei, Shengshu; Shi, Lei; Li, Hao; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00133K

data_7158648
_publ_section_title
;
 Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly
 substituted 3-fluoropyridines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00133K
_journal_year                    2022
_chemical_formula_sum            'C22 H17 Br F N3 O2'
_chemical_formula_weight         454.29
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-07-29 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.6210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8225(3)
_cell_length_b                   20.5256(8)
_cell_length_c                   11.2425(4)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.829
_cell_measurement_theta_min      5.168
_cell_volume                     1969.94(12)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0365
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29622
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.584
_exptl_absorpt_coefficient_mu    2.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0066(11)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0386P)^2^+0.8254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3038
_reflns_number_total             3853
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00133k2.cif
_cod_data_source_block           mo_d8v191122_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158648
_shelx_estimated_absorpt_t_min   0.715
_shelx_estimated_absorpt_t_max   0.800
_shelxl_version_number           2013-4
_shelx_res_checksum              90312