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_7159608
_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 H16 O2'
_chemical_formula_sum            'C22 H16 O2'
_chemical_formula_weight         312.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-24 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.647(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4368(3)
_cell_length_b                   6.67839(14)
_cell_length_c                   22.2255(6)
_cell_measurement_reflns_used    7697
_cell_measurement_temperature    303.93(10)
_cell_measurement_theta_max      74.6870
_cell_measurement_theta_min      1.9840
_cell_volume                     1696.87(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.93(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.946
_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     -4.00  44.00   0.50    0.05    --   46.32 -37.00-120.00   96
  2  \w     32.00  60.00   0.50    0.05    --  104.25 -77.00-180.00   56
  3  \w     64.00  90.00   0.50    0.05    --  104.25 -77.00-180.00   52
  4  \w    -25.00   1.00   0.50    0.05    --   46.32 -10.00   1.00   52
  5  \w     59.00 119.00   0.50    0.05    --   46.32  10.00 175.00  120
  6  \w     94.00 158.00   0.50    0.05    --  104.25  10.00 175.00  128
  7  \w     32.00  94.00   0.50    0.05    --  104.25 -94.00 -90.00  124
  8  \w     37.00 103.00   0.50    0.05    --  104.25 -94.00-150.00  132
  9  \w     38.00  70.00   0.50    0.05    --  104.25 -94.00  90.00   64
 10  \w    -40.00  26.00   0.50    0.05    --  -46.32  37.00 150.00  132
 11  \w    -22.00   3.00   0.50    0.05    --  -46.32  10.00 175.00   50
 12  \w    -67.00 -29.00   0.50    0.05    -- -102.00  61.00  90.00   76
 13  \w    -69.00 -44.00   0.50    0.05    -- -102.00  61.00   0.00   50
 14  \w    -66.00 -30.00   0.50    0.05    -- -102.00  61.00-120.00   72
 15  \w    -63.00 -37.00   0.50    0.05    -- -102.00 125.00 -60.00   52
 16  \w   -112.00 -68.00   0.50    0.05    -- -102.00 125.00 -60.00   88
 17  \w   -116.00 -34.00   0.50    0.05    --  -46.32 -10.00   1.00  164
 18  \w   -174.00 -85.00   0.50    0.05    -- -102.00 -61.00 -60.00  178
 19  \w   -147.00 -85.00   0.50    0.05    -- -102.00 -10.00   1.00  124
 20  \w   -138.00 -85.00   0.50    0.05    -- -102.00 -61.00 120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0500821000
_diffrn_orient_matrix_UB_12      0.0004649000
_diffrn_orient_matrix_UB_13      0.0635746000
_diffrn_orient_matrix_UB_21      0.1237111000
_diffrn_orient_matrix_UB_22      -0.0343678000
_diffrn_orient_matrix_UB_23      0.0273344000
_diffrn_orient_matrix_UB_31      0.0187500000
_diffrn_orient_matrix_UB_32      0.2281025000
_diffrn_orient_matrix_UB_33      0.0040069000
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10857
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.059
_diffrn_reflns_theta_min         3.980
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (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    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0637P)^2^+0.1194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2776
_reflns_number_total             3353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01500a2.cif
_cod_data_source_block           caojianhe-huang-0507_auto
_cod_depositor_comments
'Adding full bibliography for 7159607--7159608.cif.'
_cod_original_cell_volume        1696.87(8)
_cod_database_code               7159608
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.21
_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), C3(H3), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              19657
_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 3.970
_oxdiff_exptl_absorpt_empirical_full_min 0.390