Copper-Catalyzed Synthesis of Substituted Quinazolines from Benzonitriles and 2-Ethynylanilines via Carbon-Carbon Bond Cleavage Using Molecular Oxygen.
Wang, Xu; He, Dandan; Huang, Yubing; Fan, Qihang; Wu, Wanqing; Jiang, Huanfeng; The Journal of organic chemistry 83 (2018) 5458–5466; doi:10.1021/acs.joc.8b00378

data_4034822
_publ_section_title
;
 Copper-Catalyzed Synthesis of Substituted Quinazolines from Benzonitriles
 and 2-Ethynylanilines via Carbon-Carbon Bond Cleavage Using Molecular
 Oxygen.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5458
_journal_page_last               5466
_journal_paper_doi               10.1021/acs.joc.8b00378
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H14 N2'
_chemical_formula_sum            'C20 H15 N2 O0'
_chemical_formula_weight         283.34
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.52(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.617(2)
_cell_length_b                   6.9496(14)
_cell_length_c                   20.782(6)
_cell_measurement_reflns_used    8312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4090
_cell_measurement_theta_min      4.2750
_cell_volume                     1436.1(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13059
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1976
_reflns_number_gt                1246
_reflns_number_total             3265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00378_si_002.cif
_cod_data_source_block           1
_cod_database_code               4034822
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), C1(H1), C3(H3), C16(H16), C11(H11), C15(H15), C64(H64),
 C18(H18), C9(H9), C19(H19), C2(H2), C4(H4), C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'