Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes-Functionalized Fluorinated Building Blocks for Organic Synthesis.
Motornov, Vladimir A.; Muzalevskiy, Vasiliy M.; Tabolin, Andrey A.; Novikov, Roman A.; Nelyubina, Yulia V.; Nenajdenko, Valentine G.; Ioffe, Sema L.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00578

data_4032502
_publ_section_title
;
 Radical Nitration-Debromination of \a-Bromo-\a-fluoroalkenes as a
 Stereoselective Route to Aromatic \a-Fluoronitroalkenes-Functionalized
 Fluorinated Building Blocks for Organic Synthesis.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00578
_journal_year                    2017
_chemical_formula_moiety         'C10 H10 F N O4'
_chemical_formula_sum            'C10 H10 F N O4'
_chemical_formula_weight         227.19
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.026(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.8582(14)
_cell_length_b                   8.4793(8)
_cell_length_c                   17.1636(17)
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_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     2011.9(3)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
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_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    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_min       -17
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         1.473
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
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_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
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_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0967P)^2^+1.8718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3344
_reflns_number_total             4390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00578_si_002.cif
_cod_data_source_block           TA2041
_cod_database_code               4032502
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2014/6
_shelx_res_checksum              834
_shelx_hkl_checksum              14945