Copper-Catalysed Cross-Coupling Affected by the Smiles Rearrangement: A New Chapter on Diversifying the Synthesis of Chiral Fluorinated 1,4-Benzoxazine Derivatives
Alapour, Saba; Ramjugernath, Deresh; Koorbanally, Neil; RSC Adv.  (2015) –; doi:10.1039/C5RA18897K

data_7222343
_publ_section_title
;
 Copper-Catalysed Cross-Coupling Affected by the Smiles Rearrangement: A
 New Chapter on Diversifying the Synthesis of Chiral Fluorinated
 1,4-Benzoxazine Derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA18897K
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H19 Br N O3'
_chemical_formula_sum            'C14 H19 Br N O3'
_chemical_formula_weight         329.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-06-26T11:25:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-06-30 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.153(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.738(2)
_cell_length_b                   5.1422(4)
_cell_length_c                   12.9446(11)
_cell_measurement_reflns_used    13144
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      1.63
_cell_measurement_wavelength     0.71073
_cell_volume                     1525.2(2)
_computing_cell_refinement       'SAINT-plus (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2012)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13144
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.758
_diffrn_reflns_theta_min         1.63
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.699
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.399
_refine_diff_density_min         -1.199
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+13.4737P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1815
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3103
_reflns_number_total             3751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra18897k2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7222343
_shelx_estimated_absorpt_t_min   0.488
_shelx_estimated_absorpt_t_max   0.756