Catalyst-free ambient temperature synthesis of isoquinoline-fused benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination
Mishra, Manisha; Twardy, Dylan; Ellstrom, Clifford; Wheeler, Kraig A.; Dembinski, Roman; Török, Béla; Green Chemistry 21 (2019) 99–; doi:10.1039/C8GC02520G

data_7231899
_publ_section_title
;
 Catalyst-free ambient temperature synthesis of isoquinoline-fused
 benzimidazoles from 2-alkynylbenzaldehydes via alkyne hydroamination
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              99
_journal_paper_doi               10.1039/C8GC02520G
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C17 H14 N2'
_chemical_formula_sum            'C17 H14 N2'
_chemical_formula_weight         246.30
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-12-20 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.794(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_c                   16.4623(11)
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_cell_measurement_temperature    100(2)
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_cell_measurement_theta_min      4.70
_cell_volume                     2485.2(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
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_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
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_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36041
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.213
_diffrn_reflns_theta_min         3.391
_diffrn_source                   'fine-focus sealed tube'
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_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
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_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.094
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0861
_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^)+(0.1476P)^2^+2.1076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2373
_refine_ls_wR_factor_ref         0.2635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3189
_reflns_number_total             4524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc02520g2.cif
_cod_data_source_block           17demb03
_cod_depositor_comments
'Adding full bibliography for 7231898--7231899.cif.'
_cod_database_code               7231899
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.893
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              17828