Transition-metal-free C–N and C–C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines and 2-pyridones from ynones
Teng, Qing-Hu; Peng, Xiang-Jun; Mo, Zu-Yu; Xu, Yan-Li; Tang, Hai-Tao; Wang, Heng-Shan; Sun, Hong-Bin; Pan, Ying-Ming; Green Chemistry 20 (2018) 2007–; doi:10.1039/C8GC00069G

data_7230285
_publ_section_title
;
 Transition-metal-free C--N and C--C formation: synthesis of
 benzo[4,5]imidazo[1,2-a]pyridines and 2-pyridones from ynones
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2007
_journal_paper_doi               10.1039/C8GC00069G
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-24 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                68.185(4)
_cell_angle_beta                 78.205(4)
_cell_angle_gamma                88.782(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4619(4)
_cell_length_b                   9.7534(4)
_cell_length_c                   10.5387(5)
_cell_measurement_reflns_used    5656
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6050
_cell_measurement_theta_min      4.6150
_cell_volume                     882.26(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_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     38.00  87.00   0.50    0.50    --    0.00  57.00 120.00   98
  2  \w     38.00  89.00   0.50    0.50    --    0.00  38.00 -60.00  102
  3  \w    -19.00  25.00   0.50    0.50    --    0.00 -77.00-180.00   88
  4  \w     47.00  73.00   0.50    0.50    --    0.00  38.00   0.00   52
  5  \w    -15.00  33.00   0.50    0.50    --    0.00  38.00 -60.00   96
  6  \w    -48.00 -21.00   0.50    0.50    --    0.00 -77.00-180.00   54
  7  \w    -11.00  14.00   0.50    0.50    --    0.00  38.00   0.00   50
  8  \w     40.00  81.00   0.50    0.50    --   95.20 -61.00 -30.00   82
  9  \w     43.00 112.00   0.50    0.50    --   95.20 -30.00 -60.00  138
 10  \w     66.00 133.00   0.50    0.50    --   95.20  77.00 -90.00  134
 11  \w     56.00 111.00   0.50    0.50    --   95.20 -30.00  30.00  110
 12  \w      7.00 119.00   0.50    0.50    --   95.20 -82.00 -30.00  224
 13  \w     74.00 101.00   0.50    0.50    --   95.20 -82.00 120.00   54
 14  \w     92.00 118.00   0.50    0.50    --   95.20 -77.00  90.00   52
 15  \w      9.00  48.00   0.50    0.50    --   95.20 -30.00  30.00   78
 16  \w     50.00 116.00   0.50    0.50    --   95.20 -82.00  60.00  132
 17  \w      8.00  34.00   0.50    0.50    --   95.20 -30.00 -60.00   52
 18  \w      7.00 114.00   0.50    0.50    --   95.20 -15.00   0.00  214
 19  \w     68.00 105.00   0.50    0.50    --   95.20 -82.00 -90.00   74
 20  \w     13.00  52.00   0.50    0.50    --   95.20 -82.00 -90.00   78
 21  \w     29.00  55.00   0.50    0.50    --   95.20 -82.00-120.00   52
 22  \w     62.00 105.00   0.50    0.50    --   95.20 -82.00-120.00   86
 23  \w    110.00 183.00   0.50    0.50    --   95.20  45.00 -30.00  146
 24  \w     94.00 125.00   0.50    0.50    --   95.20 -82.00   0.00   62
 25  \w      7.00 109.00   0.50    0.50    --   95.20 -45.00 150.00  204
 26  \w    160.00 185.00   0.50    0.50    --   95.20  77.00 -90.00   50
 27  \w     89.00 117.00   0.50    0.50    --   95.20 -82.00 145.13   56
 28  \w     31.00  62.00   0.50    0.50    --   95.20 -82.00 145.13   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): 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      0.1414242000
_diffrn_orient_matrix_UB_12      0.0970131000
_diffrn_orient_matrix_UB_13      -0.0445146000
_diffrn_orient_matrix_UB_21      0.0737121000
_diffrn_orient_matrix_UB_22      -0.1318700000
_diffrn_orient_matrix_UB_23      0.0905699000
_diffrn_orient_matrix_UB_31      0.0482859000
_diffrn_orient_matrix_UB_32      -0.0474319000
_diffrn_orient_matrix_UB_33      -0.1255859000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8621
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.775
_diffrn_reflns_theta_min         4.624
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_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         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0624P)^2^+0.2352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3169
_reflns_number_total             3439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc00069g2.cif
_cod_data_source_block           814
_cod_depositor_comments
'Adding full bibliography for 7230285--7230286.cif.'
_cod_database_code               7230285
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.910
_reflns_odcompleteness_completeness 99.33
_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:
 C5(H5), C3(H3), C8(H8), C12(H12), C18(H18), C9(H9), C20(H20), C24(H24),
 C14(H14), C11(H11), C23(H23), C15(H15), C21(H21), C17(H17), C16(H16), C22(H22)
2.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.388
_oxdiff_exptl_absorpt_empirical_full_min 0.679