Gold-catalyzed bicyclic annulations between 4-hydroxy-1,5-diynamides and nitrones for the synthesis of cyclopentene-fused isoxazole carboxamides
Maitra, Chandrima; Chuang, Ting-Yi; Yang, Tzuhsiung; Liu, Rai-Shung; Chemical Communications 61 (2025) 8931–8934; doi:10.1039/D5CC00353A

data_7134544
_publ_section_title
;
 Gold-catalyzed bicyclic annulations between 4-hydroxy-1,5-diynamides and
 nitrones for the synthesis of cyclopentene-fused isoxazole carboxamides
;
_journal_issue                   49
_journal_name_full               'Chemical Communications'
_journal_page_first              8931
_journal_page_last               8934
_journal_paper_doi               10.1039/D5CC00353A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C33 H29 Cl N2 O4 S'
_chemical_formula_sum            'C33 H29 Cl N2 O4 S'
_chemical_formula_weight         585.09
_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             2024-07-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-07 deposited with the CCDC.	2025-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                110.3010(10)
_cell_angle_beta                 109.5870(10)
_cell_angle_gamma                94.9160(10)
_cell_formula_units_Z            4
_cell_length_a                   13.71300(10)
_cell_length_b                   14.02180(10)
_cell_length_c                   18.2490(2)
_cell_measurement_reflns_used    30536
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6270
_cell_measurement_theta_min      3.4430
_cell_volume                     3018.42(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.945
_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     99.00 139.00   0.50    0.06    --  111.34  15.00-150.00   80
  2  \w    113.00 168.00   0.50    0.06    --  111.34  64.00 -94.00  110
  3  \w    104.00 130.00   0.50    0.06    --  111.34  15.00  30.00   52
  4  \w     99.00 132.00   0.50    0.06    --  111.34  15.00  60.00   66
  5  \w    101.00 138.00   0.50    0.06    --  111.34  15.00  90.00   74
  6  \w    100.00 133.00   0.50    0.06    --  111.34  15.00 120.00   66
  7  \w     42.00  68.00   0.50    0.06    --  111.34 -77.00 120.00   52
  8  \w     43.00  74.00   0.50    0.06    --  111.34 -77.00 150.00   62
  9  \w     38.00  76.00   0.50    0.06    --  111.34 -77.00-150.00   76
 10  \w     38.00  63.00   0.50    0.06    --  111.34 -77.00-120.00   50
 11  \w    -20.00   6.00   0.50    0.05    --   42.67 -64.00 129.00   52
 12  \w    -33.00  20.00   0.50    0.05    --   42.67 -38.00 150.00  106
 13  \w     26.00  55.00   0.50    0.05    --   42.67 -64.00 129.00   58
 14  \w     42.00  89.00   0.50    0.06    --  111.34 -95.00 -60.00   94
 15  \w      3.00  67.00   0.50    0.05    --   42.67 -99.00  30.00  128
 16  \w    -15.00  17.00   0.50    0.05    --  -42.67  38.00-180.00   64
 17  \w    -51.00  28.00   0.50    0.05    --  -42.67  64.00 -94.00  158
 18  \w    -15.00  21.00   0.50    0.05    --  -42.67  38.00 -30.00   72
 19  \w    -70.00 -37.00   0.50    0.06    -- -103.00  77.00  30.00   66
 20  \w    -71.00 -43.00   0.50    0.06    -- -103.00  77.00  60.00   56
 21  \w    -70.00 -29.00   0.50    0.06    -- -103.00  77.00 120.00   82
 22  \w    -70.00 -30.00   0.50    0.06    -- -103.00  77.00  90.00   80
 23  \w    -72.00 -47.00   0.50    0.06    -- -103.00  77.00-120.00   50
 24  \w    -70.00 -32.00   0.50    0.06    -- -103.00  77.00-150.00   76
 25  \w   -131.00-103.00   0.50    0.06    -- -103.00 -15.00-150.00   56
 26  \w   -145.00-102.00   0.50    0.06    -- -103.00 -77.00-120.00   86
 27  \w   -174.00-106.00   0.50    0.06    -- -103.00 -95.00-150.00  136
 28  \w   -174.00-137.00   0.50    0.06    -- -103.00 -64.00 129.00   74
 29  \w   -139.00-102.00   0.50    0.06    -- -103.00 -64.00 129.00   74
 30  \w      5.00  37.00   0.50    0.05    --   42.67 -99.00 -90.00   64
 31  \w    -34.00  20.00   0.50    0.05    --   42.67 -38.00 120.00  108
 32  \w    -15.00  31.00   0.50    0.05    --   42.67 -57.00 -60.00   92
 33  \w    -30.00  41.00   0.50    0.05    --   42.67 -57.00  30.00  142
 34  \w    -30.00  12.00   0.50    0.05    --   42.67 -38.00-120.00   84
 35  \w     51.00  76.00   0.50    0.05    --   42.67 -99.00 -90.00   50
 36  \w    -24.00  21.00   0.50    0.05    --   42.67 -38.00  90.00   90
 37  \w    -93.00 -68.00   0.50    0.06    -- -103.00 102.00 -34.71   50
 38  \w   -129.00-103.00   0.50    0.06    -- -103.00 -15.00 -60.00   52
 39  \w    -69.00 -34.00   0.50    0.06    -- -103.00 125.00 -90.00   70
 40  \w    -66.00 -32.00   0.50    0.06    -- -103.00  77.00 -60.00   68
 41  \w    -96.00 -70.00   0.50    0.06    -- -103.00 125.00  30.00   52
 42  \w    -97.00 -72.00   0.50    0.06    -- -103.00 115.00-164.16   50
 43  \w    -92.00 -67.00   0.50    0.06    -- -103.00  98.00 168.73   50
 44  \w   -132.00 -95.00   0.50    0.06    -- -103.00 -15.00-120.00   74
 45  \w    -60.00 -32.00   0.50    0.06    -- -103.00 114.00 154.58   56
 46  \w    -93.00 -50.00   0.50    0.06    -- -103.00 102.00 128.62   86
 47  \w    -96.00 -70.00   0.50    0.06    -- -103.00 114.00 -76.88   52
 48  \w   -162.00-115.00   0.50    0.06    -- -103.00 -30.00-120.00   94
 49  \w    -61.00 -32.00   0.50    0.06    -- -103.00 116.00 102.52   58
 50  \w   -153.00-122.00   0.50    0.06    -- -103.00 -30.00 -30.00   62
 51  \w   -118.00 -93.00   0.50    0.06    -- -103.00 -30.00 -30.00   50
 52  \w    -61.00 -35.00   0.50    0.06    -- -103.00 102.00  23.09   52
 53  \w    -93.00 -66.00   0.50    0.06    -- -103.00 102.00  23.09   54
 54  \w    -97.00 -69.00   0.50    0.06    -- -103.00 114.00 154.58   56
 55  \w    -64.00 -32.00   0.50    0.06    -- -103.00 125.00  30.00   64
 56  \w     66.00  92.00   0.50    0.06    --  111.34 -95.00  90.00   52
 57  \w     54.00  91.00   0.50    0.06    --  111.34 -95.00-120.00   74
 58  \w     41.00  92.00   0.50    0.06    --  111.34 -95.00   0.00  102
 59  \w     42.00  92.00   0.50    0.06    --  111.34 -95.00-150.00  100
 60  \w     60.00  90.00   0.50    0.06    --  111.34 -95.00 -30.00   60
 61  \w     41.00  92.00   0.50    0.06    --  111.34 -95.00 120.00  102
 62  \w     55.00  81.00   0.50    0.06    --  111.34 -95.00  30.00   52
 63  \w     67.00  92.00   0.50    0.06    --  111.34 -95.00  60.00   50
 64  \w     51.00  92.00   0.50    0.06    --  111.34 -95.00 -90.00   82
 65  \w     66.00  91.00   0.50    0.06    --  111.34 -95.00 -60.00   50
 66  \w     66.00  93.00   0.50    0.06    --  111.34 -98.00  56.33   54
 67  \w    153.00 178.00   0.50    0.06    --  111.34 125.00   0.00   50
 68  \w    101.00 139.00   0.50    0.06    --  111.34  15.00-180.00   76
;
_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      -0.0353232000
_diffrn_orient_matrix_UB_12      0.0656322000
_diffrn_orient_matrix_UB_13      0.0696188000
_diffrn_orient_matrix_UB_21      -0.0186303000
_diffrn_orient_matrix_UB_22      -0.0950134000
_diffrn_orient_matrix_UB_23      0.0217212000
_diffrn_orient_matrix_UB_31      0.1157943000
_diffrn_orient_matrix_UB_32      0.0338350000
_diffrn_orient_matrix_UB_33      0.0651286000
_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  0.0243
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43959
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.233
_diffrn_reflns_theta_min         3.452
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00046(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     744
_refine_ls_number_reflns         12106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+2.3675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11379
_reflns_number_total             12106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00353a2.cif
_cod_data_source_block           240644lt_auto
_cod_depositor_comments
'Adding full bibliography for 7134542--7134544.cif.'
_cod_original_cell_volume        3018.42(5)
_cod_database_code               7134544
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.759
_shelx_estimated_absorpt_t_min   0.705
_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 Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C43(H43), C46(H46), C48(H48)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C47(H47A,H47B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C36(H36),
  C37(H37), C39(H39), C40(H40), C52(H52), C53(H53), C54(H54), C55(H55),
 C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C64(H64), C65(H65), C66(H66),
  C67(H67), C68(H68), C77(H77), C78(H78), C80(H80), C81(H81)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C41(H41A,H41B,H41C), C74(H74A,H74B,H74C), C82(H82A,H82B,
 H82C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              37588
_shelx_hkl_checksum              78748
_shelx_fab_checksum              91288
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.861