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_7247301
_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         'C29 H27 N O5'
_chemical_formula_sum            'C29 H27 N O5'
_chemical_formula_weight         469.51
_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                79.529(3)
_cell_angle_beta                 88.302(3)
_cell_angle_gamma                75.050(4)
_cell_formula_units_Z            4
_cell_length_a                   11.0361(5)
_cell_length_b                   14.2348(5)
_cell_length_c                   16.7656(6)
_cell_measurement_reflns_used    6385
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.0380
_cell_measurement_theta_min      2.6510
_cell_volume                     2501.88(18)
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.829
_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    -15.00  83.00   1.00    6.00    --   11.90  57.00 -90.00   98
  2  \w     36.00  62.00   1.00    6.00    --   11.90 178.00  90.00   26
  3  \w    -19.00  77.00   1.00    6.00    --   11.90  77.00  30.00   96
  4  \w    -57.00  38.00   1.00    6.00    --   11.90 -57.00 120.00   95
;
_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      -0.0406179000
_diffrn_orient_matrix_UB_12      0.0477817000
_diffrn_orient_matrix_UB_13      -0.0009119000
_diffrn_orient_matrix_UB_21      0.0478808000
_diffrn_orient_matrix_UB_22      0.0215860000
_diffrn_orient_matrix_UB_23      -0.0177091000
_diffrn_orient_matrix_UB_31      -0.0220082000
_diffrn_orient_matrix_UB_32      -0.0004868000
_diffrn_orient_matrix_UB_33      -0.0392069000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21663
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.611
_diffrn_reflns_theta_min         2.107
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45128
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.122
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         11671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0622P)^2^+0.9371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7873
_reflns_number_total             11671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02073h2.cif
_cod_data_source_block           1207-01
_cod_depositor_comments
'Adding full bibliography for 7247297--7247301.cif.'
_cod_database_code               7247301
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00T(H00A,H00B), C20(H20A,H20B), C013(H01A,H01B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C2(H2), C00Z(H00Z), C11(H11), C014(H014), C015(H015),
 C016(H016), C27(H27), C7(H7), C23(H23), C17(H17), C24(H24), C13(H13),
 C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J), C10(H10), C9(H9), C01N(H01N),
 C8(H8), C01P(H01P), C16(H16), C14(H14), C01T(H01T), C01V(H01V), C15(H15)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C01E(H01C,H01D,H01E), C01R(H01F,H01K,H01L), C28(H28A,
 H28B,H28C), C01X(H01M,H01O,H01Q), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              93591
_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 1.569
_oxdiff_exptl_absorpt_empirical_full_min 0.489