Thiazolium salt-catalyzed [3 + 2 + 1] cyclization for the synthesis of trisubstituted 2-pyrones using arylglyoxals as a carbonyl source
Xu, Li-Chen; Zhou, Peng; Li, Jia-Zhuo; Hao, Wen-Juan; Tu, Shu-Jiang; Jiang, Bo; Organic Chemistry Frontiers 5 (2018) 753–; doi:10.1039/C7QO00899F

data_1553934
_publ_section_title
;
 Thiazolium salt-catalyzed [3 + 2 + 1] cyclization for the synthesis of
 trisubstituted 2-pyrones using arylglyoxals as a carbonyl source
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              753
_journal_paper_doi               10.1039/C7QO00899F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C16 H14 O7'
_chemical_formula_weight         318.27
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-09-19 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                77.7590(10)
_cell_angle_beta                 76.1000(10)
_cell_angle_gamma                88.981(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9340(5)
_cell_length_b                   9.4461(8)
_cell_length_c                   12.5549(11)
_cell_measurement_reflns_used    798
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.289
_cell_measurement_theta_min      2.225
_cell_volume                     779.63(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0911
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3940
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1689
_refine_ls_R_factor_gt           0.1071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1178P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2366
_refine_ls_wR_factor_ref         0.2612
_reflns_number_gt                1243
_reflns_number_total             2682
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00899f2.cif
_cod_data_source_block           150610a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1553934