Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromobenzaldehydes, Aryl Methyl Ketones, and Sodium Azide: Access to 1 H-[1,2,3]Triazolo[4,5- c]quinoline Derivatives.
Xu, Cheng; Jiang, Shi-Fen; Wu, Yan-Dong; Jia, Feng-Cheng; Wu, An-Xin; The Journal of organic chemistry 83 (2018) 14802–14810; doi:10.1021/acs.joc.8b02476

data_4035717
_publ_section_title
;
 Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromobenzaldehydes,
 Aryl Methyl Ketones, and Sodium Azide: Access to 1 H-[1,2,3]Triazolo[4,5-
 c]quinoline Derivatives.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14802
_journal_page_last               14810
_journal_paper_doi               10.1021/acs.joc.8b02476
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C18 H16 N4 O3 S'
_chemical_formula_weight         368.41
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.069(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0620(13)
_cell_length_b                   19.221(3)
_cell_length_c                   11.3185(18)
_cell_measurement_reflns_used    4254
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.57
_cell_volume                     1721.3(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18319
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.315
_diffrn_reflns_theta_min         2.118
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       Block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5497
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0796P)^2^+0.1530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1622
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3048
_reflns_number_total             5497
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02476_si_002.cif
_cod_data_source_block           1_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035717
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              22665
_shelx_hkl_checksum              18798