Synthesis of Functionalized 1-Aminoisoquinolines through Cascade Three-Component Reaction of ortho-Alkynylbenzaldoximes, 2H-Azirines, and Electrophiles
Hosseinijei, Reyhaneh; Zahedian Tejeneki, Hossein; Nikbakht, Ali -; Rominger, Frank -; Balalaie, Saeed; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00275B

data_7158580
_publ_section_title
;
 Synthesis of Functionalized 1-Aminoisoquinolines through Cascade
 Three-Component Reaction of ortho-Alkynylbenzaldoximes, 2H-Azirines, and
 Electrophiles
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00275B
_journal_year                    2022
_chemical_formula_sum            'C29 H21 Br N2 O'
_chemical_formula_weight         493.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-21 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.8321(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.7593(14)
_cell_length_b                   10.8788(7)
_cell_length_c                   19.9065(12)
_cell_measurement_reflns_used    4760
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      2.33
_cell_volume                     4575.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         1.928
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  0.8749
_exptl_absorpt_correction_T_min  0.8028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       brick
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.089
_refine_diff_density_max         1.036
_refine_diff_density_min         -1.107
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0277P)^2^+9.7464P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3829
_reflns_number_total             5673
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00275b2.cif
_cod_data_source_block           sba186
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7158580
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.795
_shelx_estimated_absorpt_t_max   0.855
_shelx_res_checksum              74712