Tandem Copper-Catalyzed Regioselective <i>N</i>-Arylation-Aza-Michael Addition: Synthesis of Tetracyclic 5<i>H</i>-Benzothiazolo[3,2-<i>a</i>]quinazoline Derivatives.
Honnanayakanavar, Jyoti M.; Harish, Battu; Nanubolu, Jagadeesh Babu; Suresh, Surisetti; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00275

data_4038558
_publ_section_title
;
 Tandem Copper-Catalyzed Regioselective <i>N</i>-Arylation-Aza-Michael
 Addition: Synthesis of Tetracyclic
 5<i>H</i>-Benzothiazolo[3,2-<i>a</i>]quinazoline Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00275
_journal_year                    2020
_chemical_formula_moiety         'C18 H16 N2 O2 S'
_chemical_formula_sum            'C18 H16 N2 O2 S'
_chemical_formula_weight         324.39
_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   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                66.788(5)
_cell_angle_beta                 75.559(6)
_cell_angle_gamma                76.436(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3698(18)
_cell_length_b                   10.5488(19)
_cell_length_c                   10.695(2)
_cell_measurement_reflns_used    1350
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.502
_cell_measurement_theta_min      2.388
_cell_volume                     830.5(3)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1698
_diffrn_reflns_av_unetI/netI     0.1395
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11913
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.126
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2902
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.1898
_refine_ls_R_factor_gt           0.0739
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.2094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1322
_reflns_number_total             2902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00275_si_002.cif
_cod_data_source_block           KA522_0m
_cod_database_code               4038558
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.937
_shelx_estimated_absorpt_t_max   0.950
_shelx_res_checksum              47332
_shelx_hkl_checksum              97928