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_7222344
_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 H18 Br F2 N O3'
_chemical_formula_sum            'C14 H18 Br F2 N O3'
_chemical_formula_weight         366.2
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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             2015-06-26T11:00:43-00:00
_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                 95.979(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.1112(3)
_cell_length_b                   10.0220(6)
_cell_length_c                   15.5580(9)
_cell_measurement_reflns_used    13440
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.25
_cell_measurement_theta_min      2.42
_cell_measurement_wavelength     0.71073
_cell_volume                     792.61(8)
_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 0.99
_diffrn_measured_fraction_theta_max 0.843
_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  0.0346
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13440
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.247
_diffrn_reflns_theta_min         2.421
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_T_max  0.547
_exptl_absorpt_correction_T_min  0.417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.038(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0091P)^2^+0.8889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                3147
_reflns_number_total             3440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra18897k2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7222344
_shelx_estimated_absorpt_t_min   0.478
_shelx_estimated_absorpt_t_max   0.584