Pd-Catalyzed regioselective synthesis of 2,6-disubstituted pyridines through denitrogenation of pyridotriazoles and 3,8-diarylation of imidazo[1,2-a]pyridines
Joshi, Abhisek; Semwal, Rashmi; Suresh, Eringathodi; Adimurthy, Subbarayappa; Chemical Communications  (2019) –; doi:10.1039/C9CC05953A

data_7124055
_publ_section_title
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 Pd-Catalyzed regioselective synthesis of 2,6-disubstituted pyridines
 through denitrogenation of pyridotriazoles and 3,8-diarylation of
 imidazo[1,2-a]pyridines
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05953A
_journal_year                    2019
_chemical_formula_sum            'C26 H19 Cl N2'
_chemical_formula_weight         394.88
_chemical_name_common            ORGANIC
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2019-05-03 deposited with the CCDC.    2019-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                88.001(4)
_cell_angle_beta                 82.013(4)
_cell_angle_gamma                86.808(4)
_cell_formula_units_Z            4
_cell_length_a                   10.1349(13)
_cell_length_b                   10.2908(14)
_cell_length_c                   19.540(3)
_cell_measurement_reflns_used    7091
_cell_measurement_temperature    302.(2)
_cell_measurement_theta_max      24.4465
_cell_measurement_theta_min      2.2194
_cell_volume                     2014.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      302.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40777
_diffrn_reflns_theta_full        24.79
_diffrn_reflns_theta_max         24.79
_diffrn_reflns_theta_min         2.22
_diffrn_source_type              'MICRO FOCUS TUBE'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0596P)^2^+0.2511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                3963
_reflns_number_total             6890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05953a2.cif
_cod_data_source_block           CHA214FX
_cod_depositor_comments
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The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI SCAN' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4973 2017-02-22 13:04:09Z antanas 
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_cod_database_code               7124055
_shelx_res_checksum              14303