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_4038561
_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         'C17 H13 N3 S'
_chemical_formula_sum            'C17 H13 N3 S'
_chemical_formula_weight         291.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.285(3)
_cell_length_b                   14.446(5)
_cell_length_c                   12.198(4)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.189
_cell_measurement_theta_min      2.816
_cell_volume                     1459.9(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.986
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19915
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_min         2.820
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0337
_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          0.1047
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                3061
_reflns_number_total             3440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00275_si_004.cif
_cod_data_source_block           KA691_0m
_cod_database_code               4038561
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              28652
_shelx_hkl_checksum              72963