Facile dearomatization of nitroaromatic compounds using lithium enolates of unsaturated ketones in conjugate additions and (4+2) formal cycloadditions
Pasturaud, Karine; Rkein, Batoul; Sanselme, Morgane; Sebban, Muriel; Lakhdar, Sami; Durandetti, Muriel; LEGROS, Julien; Chataigner, Isabelle; Chemical Communications  (2019) –; doi:10.1039/C9CC02924A

data_7123546
_publ_section_title
;
 Facile dearomatization of nitroaromatic compounds using lithium enolates
 of unsaturated ketones in conjugate additions and (4+2) formal
 cycloadditions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02924A
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H19 Br1 N2 O6 S1'
_chemical_formula_sum            'C20 H19 Br N2 O6 S'
_chemical_formula_weight         495.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2017-11-22T09:48:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-03-20 deposited with the CCDC.    2019-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.998(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7343(11)
_cell_length_b                   12.8521(13)
_cell_length_c                   15.5222(15)
_cell_measurement_reflns_used    2242
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.06
_cell_measurement_wavelength     0.71073
_cell_volume                     2129.7(4)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELSX-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.061
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12228
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    2.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.065
_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     274
_refine_ls_number_reflns         4346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+1.1928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1998
_reflns_number_gt                2242
_reflns_number_total             4346
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c9cc02924a2.cif
_cod_data_source_block           brr221
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7123546