Pd-Catalyzed annulation of imidazo[1,2-a]pyridines with coumarins and indoles: Synthesis of benzofuran and indole fused heterocycles
Subbarayappa, Adimurthy; Semwal, Rashmi; Bhadani, Gaurav; Chemical Communications  (2022) –; doi:10.1039/D1CC06803B

data_7129478
_publ_section_title
;
 Pd-Catalyzed annulation of imidazo[1,2-a]pyridines with coumarins and
 indoles: Synthesis of benzofuran and indole fused heterocycles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06803B
_journal_year                    2022
_chemical_formula_sum            'C22 H14 Cl N3'
_chemical_formula_weight         355.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-26 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.212(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.667(2)
_cell_length_b                   13.2247(15)
_cell_length_c                   7.1270(7)
_cell_measurement_reflns_used    3399
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.33
_cell_volume                     1648.1(3)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.1367
_diffrn_reflns_av_unetI/netI     0.1106
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            33131
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         1.931
_diffrn_source                   'MICRO FOCUS TUBE'
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.027
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.5633
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7145
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0523P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                4725
_reflns_number_total             7145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06803b2.cif
_cod_data_source_block           DLR88_0ma_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'multi scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7129478
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              48444
_shelx_hkl_checksum              38398