Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles
Motornov, Vladimir A.; Tabolin, Andrey A.; Ioffe, Sema L.; New Journal of Chemistry 46 (2022) 4134–4141; doi:10.1039/D1NJ05332A

data_7061252
_publ_section_title
;
 Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the
 presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused
 heterocycles
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4134
_journal_page_last               4141
_journal_paper_doi               10.1039/D1NJ05332A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C24 H16 Cl F N2 O'
_chemical_formula_sum            'C24 H16 Cl F N2 O'
_chemical_formula_weight         402.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-09-03 deposited with the CCDC.	2022-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.945(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.2572(12)
_cell_length_b                   10.8688(5)
_cell_length_c                   13.4118(6)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.80
_cell_measurement_theta_min      2.43
_cell_volume                     3735.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            54826
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.140
_diffrn_reflns_theta_min         2.035
_diffrn_source                   'sealed X-Ray tube'
_diffrn_source_current           30
_diffrn_source_power             50
_diffrn_source_size              '0.6 mm, fine-focus'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.440
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         7131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0433P)^2^+4.4024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5652
_reflns_number_total             7131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05332a2.cif
_cod_data_source_block           VM1966
_cod_depositor_comments
'Adding full bibliography for 7061251--7061253.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7061252
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.890
_shelx_estimated_absorpt_t_max   0.904
_shelx_res_checksum              3772