Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienaymé and TBAB-Mediated Cascade Reaction in One Pot.
Li, Yong; Huang, Jiu-Hong; Wang, Juan-Li; Song, Gui-Ting; Tang, Dian-Yong; Yao, Fang; Lin, Hui-Kuan; Yan, Wei; Li, Hong-Yu; Xu, Zhi-Gang; Chen, Zhong-Zhu; The Journal of organic chemistry 84 (2019) 12632–12638; doi:10.1021/acs.joc.9b01385

data_4033991
_publ_section_title
;
 Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer
 Activity via the Groebke-Blackburn-Bienaym\'e and TBAB-Mediated Cascade
 Reaction in One Pot.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12632
_journal_page_last               12638
_journal_paper_doi               10.1021/acs.joc.9b01385
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C23 H17 N3'
_chemical_formula_weight         335.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.163(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8801(4)
_cell_length_b                   10.4479(5)
_cell_length_c                   19.1470(10)
_cell_measurement_reflns_used    4947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      4.6870
_cell_measurement_theta_min      72.3500
_cell_volume                     1776.06(15)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.098
_exptl_absorpt_coefficient_mu    0.075
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.3697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2614
_reflns_number_total             3625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01385_si_002.cif
_cod_data_source_block           160930_s3_ly
_cod_original_cell_volume        1776.06(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4033991
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              7772
_shelx_hkl_checksum              17440