Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: one-pot three-component assembly of fluorinated bicyclic nitroso acetals
Motornov, Vladimir A.; Tabolin, Andrey A.; Novikov, Roman A.; Nelyubina, Yulia V.; Nenajdenko, Valentine G.; Ioffe, Sema L.; Organic Chemistry Frontiers 5 (2018) 2588–; doi:10.1039/C8QO00623G

data_1554373
_publ_section_title
;
 Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: one-pot
 three-component assembly of fluorinated bicyclic nitroso acetals
;
_journal_issue                   17
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2588
_journal_paper_doi               10.1039/C8QO00623G
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C16 H14 Cl F N2 O6'
_chemical_formula_sum            'C16 H14 Cl F N2 O6'
_chemical_formula_weight         384.74
_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
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-06-13 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.483(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4649(14)
_cell_length_b                   6.9417(6)
_cell_length_c                   15.0372(13)
_cell_measurement_reflns_used    3854
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1715.5(3)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX2 DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20566
_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         28.998
_diffrn_reflns_theta_min         2.479
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0654P)^2^+0.0212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3368
_reflns_number_total             4568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00623g2.cif
_cod_data_source_block           vm591
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554373
_shelx_estimated_absorpt_t_min   0.912
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2014/6
_shelx_res_checksum              98248
_shelx_hkl_checksum              69723