Catalyst and solvent switched divergent C−H functionalization: oxidative annulation of N-aryl substituted quinazolin-4-amine with alkynes
Meesa, Siddi Ramulu; Naikawadi, Praveen Kumar; Gugulothu, Kishan; Kota, Shiva Kumar; Organic & Biomolecular Chemistry  (2020) –; doi:10.1039/D0OB00318B

data_7157429
_publ_section_title
;
 Catalyst and solvent switched divergent C&#x2212;H functionalization:
 oxidative annulation of N-aryl substituted quinazolin-4-amine with
 alkynes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D0OB00318B
_journal_year                    2020
_chemical_formula_moiety         'C29 H21 N3 O'
_chemical_formula_sum            'C29 H21 N3 O'
_chemical_formula_weight         427.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-08-26 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                93.42(2)
_cell_angle_beta                 100.93(2)
_cell_angle_gamma                100.11(2)
_cell_formula_units_Z            4
_cell_length_a                   9.707(9)
_cell_length_b                   11.145(10)
_cell_length_c                   21.590(16)
_cell_measurement_reflns_used    3692
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.25
_cell_measurement_theta_min      2.18
_cell_volume                     2247(3)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2013/5 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51342
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.552
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      1.264
_exptl_crystal_density_method    NONE
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0071(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         7907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1430
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0717P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3723
_reflns_number_total             7907
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00318b2.cif
_cod_data_source_block           shelx
_cod_database_code               7157429
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              61213