BF3.Etherate-Mediated Friedel-Crafts Arylation of 2-Hydroxy-1,4-benzoxazines: Synthesis of 2-Aryl-1,4-benzoxazine Derivatives
Ram Tilak Naganaboina; Rama Krishna Peddinti; Journal of Organic Chemistry 78 (2013) 12819–12824; doi:10.1021/jo402254n

data_4028877
_publ_contact_author_address
;     
Department of Chemistry, Indian Institute of Technology, Roorkee-247667,
Uttarakhand, India.
;
_publ_contact_author_email
'rkpedfcy@iitr.ernet.in, ramakpeddinti@gmail.com'
_publ_contact_author_fax         '+ (91) 133 227 3560'
_publ_contact_author_name        'Rama Krishna Peddinti'
_publ_contact_author_phone       '+(91) 133 228 5438'
_publ_section_title
;
 BF3.Etherate-Mediated Friedel-Crafts Arylation of
 2-Hydroxy-1,4-benzoxazines: Synthesis of 2-Aryl-1,4-benzoxazine
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12819
_journal_page_last               12824
_journal_paper_doi               10.1021/jo402254n
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C20 H19 Cl N O6'
_chemical_formula_sum            'C20 H19 Cl N O6'
_chemical_formula_weight         404.81
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.1020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8408(4)
_cell_length_b                   18.4917(7)
_cell_length_c                   9.6835(4)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.372
_cell_volume                     1911.11(13)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33196
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.908
_exptl_absorpt_coefficient_mu    0.237
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             844.0
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.263
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0456
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3290
_reflns_number_total             3909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo402254n_si_002.cif
_cod_data_source_block           datam_a
_cod_database_code               4028877
_shelxl_version_number           2013-2
_shelx_res_checksum              32043