Gold-catalyzed oxidation of terminal alkynes to glyoxals and their reactions with 2-phenylimidazo[1,2-<i>a</i>]pyridines: one-pot synthesis of 1,2-diones.
Liao, Shengrong; Xu, Huayan; Yang, Bin; Wang, Junfeng; Zhou, Xuefeng; Lin, Xiuping; Liu, Yonghong; Organic & biomolecular chemistry 19 (2021) 8735–8739; doi:10.1039/d1ob01507a

data_7158277
_publ_section_title
;
 Gold-catalyzed oxidation of terminal alkynes to glyoxals and their
 reactions with 2-phenylimidazo[1,2-<i>a</i>]pyridines: one-pot synthesis
 of 1,2-diones.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8735
_journal_page_last               8739
_journal_paper_doi               10.1039/d1ob01507a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C22 H16 N2 O2'
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37
_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             2021-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-19 deposited with the CCDC.	2021-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.4000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2136(2)
_cell_length_b                   10.69070(10)
_cell_length_c                   8.13480(10)
_cell_measurement_reflns_used    6265
_cell_measurement_temperature    110(15)
_cell_measurement_theta_max      74.0890
_cell_measurement_theta_min      6.2220
_cell_volume                     1653.02(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(15)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_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    -31.00  29.00   0.50    0.50    --    0.00 -82.00 120.00  120
  2  \w     -9.00  30.00   0.50    0.50    --    0.00 -82.00-180.00   78
  3  \w    -17.00   9.00   0.50    0.50    --    0.00 -82.00-150.00   52
  4  \w    -30.00  25.00   0.50    0.50    --    0.00 -82.00 -30.00  110
  5  \w      6.00 126.00   0.50    1.60    --   95.80 -82.00 -60.00  240
  6  \w     81.00 185.00   0.50    1.60    --   95.80  30.00-180.00  208
  7  \w     40.00  92.00   0.50    1.60    --   95.80 -61.00 -60.00  104
  8  \w      6.00  87.00   0.50    1.60    --   95.80 -30.00 -30.00  162
  9  \w    149.00 181.00   0.50    1.60    --   95.80  45.00  30.00   64
 10  \w     10.00  37.00   0.50    1.60    --   95.80 -61.00 -60.00   54
 11  \w     90.00 116.00   0.50    1.60    --   95.80 -61.00-180.00   52
 12  \w    158.00 184.00   0.50    1.60    --   95.80  82.00-180.00   52
 13  \w     73.00 185.00   0.50    1.60    --   95.80  15.00 120.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0289588000
_diffrn_orient_matrix_UB_12      0.1310280000
_diffrn_orient_matrix_UB_13      0.0302163000
_diffrn_orient_matrix_UB_21      -0.0748018000
_diffrn_orient_matrix_UB_22      -0.0441349000
_diffrn_orient_matrix_UB_23      -0.0701907000
_diffrn_orient_matrix_UB_31      -0.0119040000
_diffrn_orient_matrix_UB_32      -0.0402893000
_diffrn_orient_matrix_UB_33      0.1755830000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8977
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.392
_diffrn_reflns_theta_min         4.653
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0590P)^2^+0.5099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2978
_reflns_number_total             3264
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01507a2.cif
_cod_data_source_block           liaoshengrong_lsr4-197-1_collect
_cod_depositor_comments          'Adding full bibliography for 7158277.cif.'
_cod_database_code               7158277
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C92 H64 N4 O8 '
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.952
_reflns_odcompleteness_completeness 99.62
_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), C21(H21), C9(H9), C13(H13), C17(H17), C4(H4), C3(H3), C10(H10),
 C2(H2), C11(H11), C12(H12), C20(H20), C18(H18)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              30661
_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 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.841