Green and effective synthesis of multisubstituted α-pyrones via K2CO3 catalyzed formal insertion of ketenimines into C(CO)–C bonds of 1,3-diketones
Luo, Jian; Zhong, Ai-Qing; Qiu, Jia-Hao; Liu, Xiong-Wei; Tian, You-Ping; Zhang, Bao-Hua; Chen, Guo-Shu; Shu, Wei; Liu, Yun-Lin; Green Chemistry 25 (2023) 8057–8067; doi:10.1039/D3GC02073H

data_7247299
_publ_section_title
;
 Green and effective synthesis of multisubstituted \a-pyrones via K2CO3
 catalyzed formal insertion of ketenimines into C(CO)--C bonds of
 1,3-diketones
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8057
_journal_page_last               8067
_journal_paper_doi               10.1039/D3GC02073H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C36 H27 N O'
_chemical_formula_sum            'C36 H27 N O'
_chemical_formula_weight         489.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-28 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                86.936(6)
_cell_angle_beta                 75.711(7)
_cell_angle_gamma                69.063(7)
_cell_formula_units_Z            2
_cell_length_a                   10.3653(9)
_cell_length_b                   11.5399(8)
_cell_length_c                   12.1483(9)
_cell_measurement_reflns_used    3520
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      72.3790
_cell_measurement_theta_min      3.6960
_cell_volume                     1314.21(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_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    -62.00  29.00   1.00    1.00    --  -40.73  38.00   0.00   91
  2  \w    -60.00  -3.00   1.00    1.00    --  -40.73  77.00 150.00   57
  3  \w     57.00  97.00   1.00    1.00    --   40.73-125.00   0.00   40
  4  \w     37.00 136.00   1.00    1.00    --  106.95 -61.00 -60.00   99
  5  \w     77.00 120.00   1.00    1.00    --  106.95-125.00   0.00   43
  6  \w     64.00 105.00   1.00    1.00    --  106.95 -94.00  60.00   41
  7  \w     31.00 134.00   1.00    1.00    --  106.95 -30.00 150.00  103
  8  \w     81.00 178.00   1.00    1.00    --  106.95  30.00 150.00   97
  9  \w    138.00 170.00   1.00    1.00    --  106.95  45.00 -30.00   32
 10  \w    134.00 162.00   1.00    1.00    --  106.95 125.00-120.00   28
 11  \w     99.00 144.00   1.00    1.00    --  106.95 125.00-150.00   45
 12  \w     94.00 123.00   1.00    1.00    --  106.95 125.00-120.00   29
 13  \w     81.00 108.00   1.00    1.00    --  106.95  45.00 -30.00   27
 14  \w     80.00 141.00   1.00    1.00    --  106.95  30.00  60.00   61
 15  \w     37.00 117.00   1.00    1.00    --  106.95-125.00-150.00   80
 16  \w     49.00 132.00   1.00    1.00    --  106.95 -77.00-180.00   83
 17  \w    -94.00 -22.00   1.00    1.00    --  -40.73 -38.00  30.00   72
 18  \w   -116.00 -15.00   1.00    1.00    --  -40.73 -77.00-150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1418741000
_diffrn_orient_matrix_UB_12      -0.0232004000
_diffrn_orient_matrix_UB_13      0.0313232000
_diffrn_orient_matrix_UB_21      0.0519335000
_diffrn_orient_matrix_UB_22      -0.0884528000
_diffrn_orient_matrix_UB_23      0.0923514000
_diffrn_orient_matrix_UB_31      -0.0640566000
_diffrn_orient_matrix_UB_32      0.1099953000
_diffrn_orient_matrix_UB_33      0.0874068000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.360
_diffrn_reflns_theta_min         3.757
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0449P)^2^+0.2544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3960
_reflns_number_total             5121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02073h2.cif
_cod_data_source_block           ly1210
_cod_depositor_comments
'Adding full bibliography for 7247297--7247301.cif.'
_cod_database_code               7247299
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.925
_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:
 C16(H16), C7(H7), C19(H19), C12(H12), C13(H13), C28(H28), C9(H9), C23(H23),
 C3(H3), C25(H25), C10(H10), C32(H32), C6(H6), C22(H22), C26(H26), C27(H27),
 C20(H20), C5(H5), C36(H36), C21(H21), C4(H4), C33(H33), C34(H34), C35(H35)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              10928
_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 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.689