A novel acid-catalyzed rearrangement of 2-substituted-3-(2-nitrophenyl)oxiranes for the synthesis of di- and mono-oxalamides
Mamedov, Vakhid A.; Mamedova, Vera L.; Khikmatova, Gul’nas Z.; Mironova, Ekaterina V.; Krivolapov, Dmitry; Bazanova, Olga B.; Chachkov, Denis V.; Katsyuba, Sergey; Rizvanov, Ildar Kh.; Latypov, Shamil Kamil'evich; RSC Adv.  (2016) –; doi:10.1039/C6RA02586B

data_7224596
_publ_section_title
;
 A novel acid-catalyzed rearrangement of
 2-substituted-3-(2-nitrophenyl)oxiranes for the synthesis of di- and
 mono-oxalamides
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA02586B
_journal_year                    2016
_chemical_formula_moiety         'C15 H11 Br N2 O4'
_chemical_formula_sum            'C15 H11 Br N2 O4'
_chemical_formula_weight         363.17
_chemical_name_systematic
N1-(2-carboxyphenyl)-N2-(4-bromophenyl)oxalamide
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-10 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                108.324(3)
_cell_angle_beta                 97.068(4)
_cell_angle_gamma                105.848(4)
_cell_formula_units_Z            4
_cell_length_a                   9.555(3)
_cell_length_b                   11.210(3)
_cell_length_c                   15.335(4)
_cell_measurement_reflns_used    7067
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      2.28
_cell_volume                     1460.2(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23079
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.01
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              SmartApexII
_exptl_absorpt_coefficient_mu    2.835
_exptl_absorpt_correction_T_max  0.6010
_exptl_absorpt_correction_T_min  0.4835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisn
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         5742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                4286
_reflns_number_total             5742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra02586b2.cif
_cod_data_source_block           v487_fin
_cod_original_cell_volume        1460.3(7)
_cod_database_code               7224596