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_7230286
_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         'C H Cl3, C24 H18 N2'
_chemical_formula_sum            'C25 H19 Cl3 N2'
_chemical_formula_weight         453.77
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-26 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.330(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6279(10)
_cell_length_b                   15.8991(10)
_cell_length_c                   13.4801(10)
_cell_measurement_reflns_used    2691
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4420
_cell_measurement_theta_min      3.8800
_cell_volume                     2240.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_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    -95.00 -34.00   1.00    5.00    --  -18.94 178.00 120.00   61
  2  \w    -49.00  40.00   1.00    5.00    --   19.33 -57.00 -60.00   89
  3  \w    -54.00  63.00   1.00    5.00    --   19.33 -19.00   0.00  117
  4  \w    -11.00  14.00   1.00    5.00    --   19.33  77.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0387135000
_diffrn_orient_matrix_UB_12      -0.0203050000
_diffrn_orient_matrix_UB_13      -0.0304979000
_diffrn_orient_matrix_UB_21      -0.0530842000
_diffrn_orient_matrix_UB_22      -0.0245186000
_diffrn_orient_matrix_UB_23      -0.0227303000
_diffrn_orient_matrix_UB_31      -0.0165368000
_diffrn_orient_matrix_UB_32      0.0312708000
_diffrn_orient_matrix_UB_33      -0.0376755000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_min         3.329
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0840
_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^)+(0.1311P)^2^+0.8741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3322
_reflns_number_total             5112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc00069g2.cif
_cod_data_source_block           20170115_pym_zhy_308
_cod_depositor_comments
'Adding full bibliography for 7230285--7230286.cif.'
_cod_database_code               7230286
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.846
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.063) H2(0.076) H3(0.078) H4(0.07) H8(0.05) H10(0.049)
 H13(0.059) H14(0.071) H15(0.088) H16(0.091) H17(0.066) H19(0.062) H20(0.074)
 H22A(0.145) H22B(0.145) H22C(0.145) H23(0.066) H24(0.057) H25(0.074)
 Fixed X: H1(0.565701) H2(0.428301) H3(0.243) H4(0.1875) H8(0.4235)
 H10(0.7421) H13(0.5898) H14(0.7245) H15(0.9228) H16(0.9889) H17(0.8556)
 H19(0.5591) H20(0.624301) H22A(0.852) H22B(0.7414) H22C(0.7185) H23(0.796399)
 H24(0.7301) H25(0.8576)
 Fixed Y: H1(0.4416) H2(0.406799) H3(0.333301) H4(0.2922) H8(0.324)
 H10(0.4503) H13(0.5771) H14(0.653501) H15(0.6005) H16(0.474699) H17(0.3966)
 H19(0.2651) H20(0.258901) H22A(0.3555) H22B(0.416499) H22C(0.3191) H23(0.481)
 H24(0.4887) H25(0.702)
 Fixed Z: H1(0.8801) H2(0.988) H3(0.9316) H4(0.7657) H8(0.4451) H10(0.5595)
 H13(0.7493) H14(0.8694) H15(0.9388) H16(0.8846) H17(0.763201) H19(0.3449)
 H20(0.192101) H22A(0.111101) H22B(0.064301) H22C(0.061201) H23(0.2448)
 H24(0.3971) H25(0.488)
;
_shelx_res_checksum              37840
_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 1.634
_oxdiff_exptl_absorpt_empirical_full_min 0.675