Copper-catalyzed N-arylation of azoles and diazoles using highly functionalized trivalent organobismuth reagents
Petiot, Pauline; Dansereau, Julien; Gagnon, Alexandre; RSC Adv. 4 (2014) 22255–; doi:10.1039/C4RA02467B

data_7235643
_publ_section_title
;
 Copper-catalyzed N-arylation of azoles and diazoles using highly
 functionalized trivalent organobismuth reagents
;
_journal_issue                   42
_journal_name_full               'RSC Adv.'
_journal_page_first              22255
_journal_paper_doi               10.1039/C4RA02467B
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C14 H9 F N2 O'
_chemical_formula_sum            'C14 H9 F N2 O'
_chemical_formula_weight         240.23
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-02-07 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 92.874(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.76530(10)
_cell_length_b                   17.7911(4)
_cell_length_c                   16.0214(3)
_cell_measurement_reflns_used    9053
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.38
_cell_measurement_theta_min      3.72
_cell_volume                     1071.90(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15339
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.371
_diffrn_reflns_theta_min         3.715
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0028(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+0.9563P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1657
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1661
_reflns_number_total             1971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra02467b2.cif
_cod_data_source_block           cu_pauline1b_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7235643
_shelx_estimated_absorpt_t_min   0.794
_shelx_estimated_absorpt_t_max   0.959
_shelxl_version_number           2013-2
_shelx_res_checksum              35213
_shelx_hkl_checksum              42967