Synthesis of 3(2<i>H</i>)-furanone derivatives: <i>p</i>-TsOH/halotrimethylsilane promoted cycloketonization of <i>γ</i>-hydroxyl ynones.
Qiu, Yi-Feng; Cao, Jian-He; Wang, Shutao; Wang, Qiang; Li, Ming; Wang, Jun-Jiao; Quan, Zheng-Jun; Wang, Xi-Cun; Organic & biomolecular chemistry 21 (2023) 8744–8748; doi:10.1039/d3ob01500a

data_7159607
_publ_section_title
;
 Synthesis of 3(2<i>H</i>)-furanone derivatives:
 <i>p</i>-TsOH/halotrimethylsilane promoted cycloketonization of
 <i>&#x3b3;</i>-hydroxyl ynones.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8744
_journal_page_last               8748
_journal_paper_doi               10.1039/d3ob01500a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C22 H15 N3 O2'
_chemical_formula_sum            'C22 H15 N3 O2'
_chemical_formula_weight         353.37
_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             2022-01-04
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-05-24 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.134(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7255(2)
_cell_length_b                   19.0167(4)
_cell_length_c                   8.36520(18)
_cell_measurement_reflns_used    8452
_cell_measurement_temperature    295.77(10)
_cell_measurement_theta_max      76.9540
_cell_measurement_theta_min      2.3290
_cell_volume                     1800.58(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.77(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.951
_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     60.00 105.00   0.50    0.05    --   47.57  28.00  93.00   90
  2  \w     97.00 133.00   0.50    0.05    --  107.75  28.00  93.00   72
  3  \w     98.00 175.00   0.50    0.05    --  107.75  37.00-180.00  154
  4  \w     38.00  63.00   0.50    0.05    --  107.75 -57.00 150.00   50
  5  \w     37.00  63.00   0.50    0.05    --  107.75 -77.00 120.00   52
  6  \w     78.00 103.00   0.50    0.05    --  107.75 -77.00 120.00   50
  7  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00 -30.00   50
  8  \w    -18.00  30.00   0.50    0.05    --   47.57 -28.00 -67.00   96
  9  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00  30.00   50
 10  \w     35.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   52
 11  \w     53.00  79.00   0.50    0.05    --  107.75 -77.00-180.00   52
 12  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00-150.00   50
 13  \w    -93.00 -26.00   0.50    0.05    --  -47.57 125.00-120.00  134
 14  \w    -74.00 -28.00   0.50    0.05    -- -100.00  77.00 -90.00   92
 15  \w   -109.00 -62.00   0.50    0.05    -- -100.00  77.00  60.00   94
 16  \w    -67.00 -28.00   0.50    0.05    -- -100.00  57.00  30.00   78
 17  \w    -69.00 -36.00   0.50    0.05    -- -100.00  57.00  90.00   66
 18  \w    -68.00 -33.00   0.50    0.05    -- -100.00  57.00   0.00   70
 19  \w    -69.00 -28.00   0.50    0.05    -- -100.00  57.00 -90.00   82
 20  \w    -62.00 -36.00   0.50    0.05    -- -100.00  57.00-120.00   52
 21  \w   -174.00 -99.00   0.50    0.05    -- -100.00 -28.00 -67.00  150
 22  \w   -122.00 -50.00   0.50    0.05    --  -47.57 -28.00 -67.00  144
 23  \w     35.00 109.00   0.50    0.05    --  107.75-125.00-180.00  148
 24  \w    -31.00  26.00   0.50    0.05    --  -47.57  28.00  93.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0859237000
_diffrn_orient_matrix_UB_12      0.0291464000
_diffrn_orient_matrix_UB_13      0.0950422000
_diffrn_orient_matrix_UB_21      -0.0969373000
_diffrn_orient_matrix_UB_22      0.0065094000
_diffrn_orient_matrix_UB_23      -0.1638925000
_diffrn_orient_matrix_UB_31      -0.0417105000
_diffrn_orient_matrix_UB_32      -0.0753075000
_diffrn_orient_matrix_UB_33      0.0226308000
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11937
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.300
_diffrn_reflns_theta_min         4.546
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0754P)^2^+0.2758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3236
_reflns_number_total             3640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01500a2.cif
_cod_data_source_block           exp_51_auto
_cod_depositor_comments
'Adding full bibliography for 7159607--7159608.cif.'
_cod_original_cell_volume        1800.58(7)
_cod_database_code               7159607
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_shelx_res_checksum              33555
_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 4.092
_oxdiff_exptl_absorpt_empirical_full_min 0.533