High Pressure promoted Dearomatization of Nitroarenes by [4+2] Cycloadditions with Silyloxydienes
Rkein, Batoul; Coffinier, Romain; Powderly, Marian; Manneveau, Maxime; Sanselme, Morgane; Durandetti, Muriel; Sebban, Muriel; Hamdoun, Ghanem; Oulyadi, Hassan; Harrowven, David; Legros, Julien; Chataigner, Isabelle; Chemical Communications  (2022) –; doi:10.1039/D2CC04778K

data_7130770
_publ_section_title
;
 High Pressure promoted Dearomatization of Nitroarenes by [4+2]
 Cycloadditions with Silyloxydienes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04778K
_journal_year                    2022
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H14 F1 N1 O4'
_chemical_formula_sum            'C15 H14 F N O4'
_chemical_formula_weight         291.27
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_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      2.4
_audit_creation_date             2020-12-02T15:07:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-08-08 deposited with the CCDC.	2022-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.883(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5797(18)
_cell_length_b                   8.1298(12)
_cell_length_c                   13.6651(19)
_cell_measurement_reflns_used    1542
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.94
_cell_measurement_wavelength     0.71073
_cell_volume                     1350.7(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5814
_diffrn_reflns_theta_full        23.24
_diffrn_reflns_theta_max         23.24
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.04
_refine_ls_extinction_coef       0.018(3)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.0660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                1542
_reflns_number_total             1923
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            d2cc04778k2.cif
_cod_data_source_block           br924
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7130770