Copper catalyzed synthesis of fused benzimidazolopyrazine derivatives via tandem benzimidazole formation/annulation of δ-alkynyl aldehyde.
Ramesh, Subburethinam; Kr Ghosh, Suman; Nagarajan, Rajagopal; Organic & biomolecular chemistry 11 (2013) 7712–7720; doi:10.1039/c3ob41044g

data_7153135
_publ_section_title
;
 Copper catalyzed synthesis of fused benzimidazolopyrazine derivatives via
 tandem benzimidazole formation/annulation of \d-alkynyl aldehyde.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7712
_journal_page_last               7720
_journal_paper_doi               10.1039/c3ob41044g
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C20 H17 N3 O0.5'
_chemical_formula_weight         307.36
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.136(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   18.482(3)
_cell_length_b                   24.976(4)
_cell_length_c                   14.268(2)
_cell_measurement_reflns_used    9344
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.22
_cell_volume                     6259.0(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
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_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             2592
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_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
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_refine_diff_density_min         -0.610
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_refine_ls_number_reflns         6180
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_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3198
_refine_ls_wR_factor_ref         0.3499
_reflns_number_gt                3918
_reflns_number_total             6180
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41044g.txt
_cod_data_source_block           rn113-2m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        6259.1(17)
_cod_original_sg_symbol_H-M      'C2/c '
_cod_database_code               7153135