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_4029499
_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         'C32 H28 N4'
_chemical_formula_sum            'C32 H28 N4'
_chemical_formula_weight         468.58
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.040(3)
_cell_angle_beta                 104.859(3)
_cell_angle_gamma                99.734(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0403(18)
_cell_length_b                   10.9408(19)
_cell_length_c                   12.564(2)
_cell_measurement_reflns_used    1283
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.1
_cell_measurement_theta_min      2.3
_cell_volume                     1313.4(4)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10111
_diffrn_reflns_theta_full        25.60
_diffrn_reflns_theta_max         25.60
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4908
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.269
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0679
_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^)+(0.1150P)^2^+0.0160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1846
_refine_ls_wR_factor_ref         0.2290
_reflns_number_gt                2466
_reflns_number_total             4908
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802166t_si_001.cif
_cod_data_source_block           5i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029499