Simple and Convenient Approach to the Kr€ohnke Pyridine Type Synthesis of Functionalized Indol-3-yl Pyridine Derivatives Using 3-Cyanoacetyl Indole
Thirumurugan, Prakasam; Nandakumar, A.; Muralidharan, D.; Perumal, Paramasivan T.; Journal of Combinatorial Chemistry 12 (2010) 161–; doi:10.1021/cc9001394

data_1502639
_publ_section_title
;
 Simple and Convenient Approach to the Kr&#x20AC;ohnke Pyridine Type
 Synthesis of Functionalized Indol-3-yl Pyridine Derivatives Using
 3-Cyanoacetyl Indole
;
_journal_coeditor_code           BT2767
_journal_issue                   1
_journal_name_full               'Journal of Combinatorial Chemistry'
_journal_page_first              161
_journal_paper_doi               10.1021/cc9001394
_journal_volume                  12
_journal_year                    2010
_chemical_formula_iupac          'C25 H16 Cl2 N4'
_chemical_formula_moiety         'C25 H16 Cl2 N4'
_chemical_formula_sum            'C25 H16 Cl2 N4'
_chemical_formula_weight         443.32
_chemical_name_common
;
4-(2,4-Dichlorophenyl)-1,4-dihydro-2-(1H-indol-3-yl)-6-(pyridine-3-
carbonitrile
;
_chemical_name_systematic
;
4-(2,4-Dichlorophenyl)-2-(1<i>H</i>-indol-3-yl)-6-(2-pyridyl)-
1,4-dihydropyridine-4-carbonitrile
;
_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           SHELXL97
_cell_angle_alpha                72.260(6)
_cell_angle_beta                 79.420(6)
_cell_angle_gamma                78.224(6)
_cell_formula_units_Z            2
_cell_length_a                   8.0158(9)
_cell_length_b                   10.0261(12)
_cell_length_c                   14.3653(17)
_cell_measurement_reflns_used    2900
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.17
_cell_volume                     1067.3(2)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
'Bruker APEX2 CCD area-detector diffractometer'
_diffrn_measurement_method       '\w and \f 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12383
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.9146
_exptl_absorpt_correction_T_min  0.8949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.639
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.5551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                3172
_reflns_number_total             3707
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cc9001394_si_003.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502639