Copper-mediated formally dehydrative biaryl coupling of azine N-oxides and oxazoles.
Odani, Riko; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro; The Journal of organic chemistry 80 (2015) 2384–2391; doi:10.1021/acs.joc.5b00037

data_4030754
_publ_section_title
;
 Copper-mediated formally dehydrative biaryl coupling of azine N-oxides
 and oxazoles.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2384
_journal_page_last               2391
_journal_paper_doi               10.1021/acs.joc.5b00037
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C18 H12 N2 O2'
_chemical_formula_sum            'C18 H12 N2 O2'
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_symmetry_cell_setting           orthorhombic
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_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            16
_cell_length_a                   10.2831(11)
_cell_length_b                   21.4073(19)
_cell_length_c                   25.129(2)
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_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     5531.7(9)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.0'
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_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 6.827
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0722
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_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
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_diffrn_reflns_limit_l_min       -32
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_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.49
_diffrn_standards_number         0
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_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2400.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
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_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         6346
_refine_ls_number_restraints     0
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_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0822P)^2^+3.8725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2145
_reflns_number_gt                4682
_reflns_number_total             6346
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
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