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_7222346
_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_formula_moiety         'C13 H15 Br F N O3'
_chemical_formula_sum            'C13 H15 Br F N O3'
_chemical_formula_weight         332.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-08-17 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                75.3280(10)
_cell_angle_beta                 89.1280(10)
_cell_angle_gamma                89.8310(10)
_cell_formula_units_Z            4
_cell_length_a                   8.0120(2)
_cell_length_b                   12.0546(3)
_cell_length_c                   14.3104(4)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      2.94
_cell_volume                     1336.90(6)
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23444
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_min         1.471
_exptl_absorpt_coefficient_mu    3.090
_exptl_absorpt_correction_T_max  0.671
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.300
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_exptl_crystal_size_min          0.140
_refine_diff_density_max         2.237
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+5.1240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4636
_reflns_number_total             4955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra18897k2.cif
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_cod_database_code               7222346
_shelx_estimated_absorpt_t_min   0.457
_shelx_estimated_absorpt_t_max   0.672
_shelxl_version_number           2014-3
_shelx_res_checksum              42562