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_7231898
_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         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-28 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.930(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9878(2)
_cell_length_b                   12.0606(7)
_cell_length_c                   24.7189(14)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.58
_cell_volume                     1186.07(11)
_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)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25948
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.210
_diffrn_reflns_theta_min         1.791
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       'transparent plate'
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4148
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0527P)^2^+0.1415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                3806
_reflns_number_total             4148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc02520g2.cif
_cod_data_source_block           17demb02
_cod_depositor_comments
'Adding full bibliography for 7231898--7231899.cif.'
_cod_database_code               7231898
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.775
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              93522