One-Pot Tandem Amidation, Knoevenagel Condensation, and Palladium-Catalyzed Wacker Type Oxidation/C-O Coupling: Synthesis of Chromeno-Annulated Imidazopyridines.
Pandey, Khima; Rangan, Krishnan; Kumar, Anil; The Journal of organic chemistry 83 (2018) 8026–8035; doi:10.1021/acs.joc.8b00884

data_4035575
_publ_section_title
;
 One-Pot Tandem Amidation, Knoevenagel Condensation, and
 Palladium-Catalyzed Wacker Type Oxidation/C-O Coupling: Synthesis of
 Chromeno-Annulated Imidazopyridines.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8026
_journal_page_last               8035
_journal_paper_doi               10.1021/acs.joc.8b00884
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H9 Cl N2 O2'
_chemical_formula_sum            'C15 H9 Cl N2 O2'
_chemical_formula_weight         284.69
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.213(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7771(3)
_cell_length_b                   21.9081(4)
_cell_length_c                   7.8071(2)
_cell_measurement_reflns_used    2715
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      74.0510
_cell_measurement_theta_min      6.3170
_cell_volume                     1203.46(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -86.00 -51.00   0.50    5.00    --    0.00 -77.00  90.00   70
  2  \w    -33.00  -7.00   0.50    5.00    --    0.00 -37.00 -90.00   52
  3  \w     -5.00  30.00   0.50    5.00    --    0.00 -77.00  90.00   70
  4  \w    -85.00 -58.00   0.50    5.00    --    0.00 -37.00 -90.00   54
  5  \w     56.00 126.00   0.50   20.00    --   95.80 -77.00 -60.00  140
  6  \w     76.00 167.00   0.50   20.00    --   95.80  30.00 -60.00  182
  7  \w    102.00 129.00   0.50   20.00    --   95.80  15.00  90.00   54
  8  \w     29.00 115.00   0.50   20.00    --   95.80 -45.00 -60.00  172
  9  \w    125.00 162.00   0.50   20.00    --   95.80  45.00  30.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0275343000
_diffrn_orient_matrix_UB_12      0.0604755000
_diffrn_orient_matrix_UB_13      0.0863521000
_diffrn_orient_matrix_UB_21      -0.0267592000
_diffrn_orient_matrix_UB_22      -0.0358185000
_diffrn_orient_matrix_UB_23      0.1565586000
_diffrn_orient_matrix_UB_31      0.2154469000
_diffrn_orient_matrix_UB_32      0.0032810000
_diffrn_orient_matrix_UB_33      0.1249185000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3647
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.264
_diffrn_reflns_theta_min         4.036
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0672P)^2^+0.5068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1817
_reflns_number_total             1912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00884_si_002.cif
_cod_data_source_block           exp-186-kp-806_reduced
_cod_database_code               4035575
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C15 N2 O2 Cl H9'
_reflns_odcompleteness_completeness 81.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C2(H2), C12(H12), C1(H1), C13(H13), C3(H3)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              45564
_shelx_hkl_checksum              54358
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.648
_oxdiff_exptl_absorpt_empirical_full_min 0.792