One-step synthesis of pyrido[1,2-a]benzimidazole derivatives by a novel multicomponent reaction of chloroacetonitrile, malononitrile, aromatic aldehyde, and pyridine.
Yan, Chao Guo; Wang, Qi Fang; Song, Xiao Kai; Sun, Jing; The Journal of organic chemistry 74 (2009) 710–718; doi:10.1021/jo802166t

data_4029493
_publ_section_title
;
 One-step synthesis of pyrido[1,2-a]benzimidazole derivatives by a novel
 multicomponent reaction of chloroacetonitrile, malononitrile, aromatic
 aldehyde, and pyridine.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              710
_journal_page_last               718
_journal_paper_doi               10.1021/jo802166t
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C28 H21 N5, C H2 Cl2'
_chemical_formula_sum            'C29 H23 Cl2 N5'
_chemical_formula_weight         512.42
_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                 107.909(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.535(3)
_cell_length_b                   10.0033(13)
_cell_length_c                   21.122(3)
_cell_measurement_reflns_used    6518
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.5
_cell_volume                     5334.9(12)
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18632
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9606
_exptl_absorpt_correction_T_min  0.9185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+8.3704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1698
_refine_ls_wR_factor_ref         0.1890
_reflns_number_gt                3584
_reflns_number_total             4693
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802166t_si_001.cif
_cod_data_source_block           J1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4029493