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_7134543
_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         'C38 H38 N2 O5 S'
_chemical_formula_sum            'C38 H38 N2 O5 S'
_chemical_formula_weight         634.76
_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             2024-02-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-28 deposited with the CCDC.	2025-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                76.205(2)
_cell_angle_beta                 81.449(2)
_cell_angle_gamma                76.849(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1231(2)
_cell_length_b                   10.6595(3)
_cell_length_c                   19.4826(7)
_cell_measurement_reflns_used    12507
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2170
_cell_measurement_theta_min      4.3280
_cell_volume                     1782.77(9)
_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  (Sheldrick, 2015)'
_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-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.938
_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     43.00  92.00   0.50    0.05    --   83.87 -99.00  -8.13   98
  2  \w     44.00  92.00   0.50    0.05    --   80.61-111.00 -30.00   96
  3  \w     40.00  93.00   0.50    0.05    --   83.87-100.00-111.89  106
  4  \w     13.00  38.00   0.50    0.05    --   56.15 -95.00-180.00   50
  5  \w     36.00  71.00   0.50    0.05    --   56.15-125.00-120.00   70
  6  \w     43.00  88.00   0.50    0.05    --   80.61 -95.00 -90.00   90
  7  \w     48.00  88.00   0.50    0.05    --   80.61 -95.00 -30.00   80
  8  \w     39.00  88.00   0.50    0.05    --   80.61 -95.00-150.00   98
  9  \w     14.00  55.00   0.50    0.05    --   56.15 -95.00 -30.00   82
 10  \w     23.00  61.00   0.50    0.05    --   56.15 -95.00 -90.00   76
 11  \w     38.00  63.00   0.50    0.05    --   80.61 -95.00  30.00   50
 12  \w     39.00  87.00   0.50    0.05    --   80.61 -95.00 120.00   96
 13  \w     24.00  63.00   0.50    0.05    --   56.15 -95.00 120.00   78
 14  \w    105.00 131.00   0.50    0.05    --   80.61  15.00  60.00   52
 15  \w     45.00 106.00   0.50    0.05    --   80.61  15.00 150.00  122
 16  \w     52.00  85.00   0.50    0.05    --   80.61  15.00  60.00   66
 17  \w     44.00 128.00   0.50    0.05    --   80.61  15.00 -90.00  168
 18  \w     77.00 113.00   0.50    0.05    --   80.61  15.00   0.00   72
 19  \w     45.00  74.00   0.50    0.05    --   80.61  15.00   0.00   58
 20  \w    -67.00 -26.00   0.50    0.05    --  -59.17 125.00   0.00   82
 21  \w    -63.00 -32.00   0.50    0.05    --  -76.67 111.00 -30.00   62
 22  \w    -97.00 -39.00   0.50    0.05    --  -81.00 114.00  41.84  116
 23  \w    -97.00 -44.00   0.50    0.05    --  -81.00 115.00 124.31  106
 24  \w    -92.00 -63.00   0.50    0.05    --  -81.00 100.00 174.59   58
 25  \w    -75.00 -32.00   0.50    0.05    --  -76.67 111.00 120.00   86
 26  \w    -92.00 -40.00   0.50    0.05    --  -76.67 111.00  90.00  104
 27  \w    -91.00 -41.00   0.50    0.05    --  -81.00  99.00  26.03  100
 28  \w    -92.00 -67.00   0.50    0.05    --  -81.00 100.00 -70.50   50
 29  \w   -120.00 -44.00   0.50    0.05    --  -76.67 -15.00  60.00  152
 30  \w   -120.00 -37.00   0.50    0.05    --  -71.74 -15.00 120.00  166
 31  \w   -127.00 -52.00   0.50    0.05    --  -76.67 -15.00 -30.00  150
 32  \w   -126.00 -46.00   0.50    0.05    --  -76.67 -15.00-150.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1700701000
_diffrn_orient_matrix_UB_12      -0.0014720000
_diffrn_orient_matrix_UB_13      -0.0202844000
_diffrn_orient_matrix_UB_21      0.0105918000
_diffrn_orient_matrix_UB_22      0.0346008000
_diffrn_orient_matrix_UB_23      0.0712634000
_diffrn_orient_matrix_UB_31      0.0365838000
_diffrn_orient_matrix_UB_32      -0.1478854000
_diffrn_orient_matrix_UB_33      0.0347341000
_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  0.0279
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21575
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.648
_diffrn_reflns_theta_min         4.359
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84592
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0649P)^2^+0.4583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6047
_reflns_number_total             6878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00353a2.cif
_cod_data_source_block           240218lt_auto
_cod_depositor_comments
'Adding full bibliography for 7134542--7134544.cif.'
_cod_original_cell_volume        1782.78(9)
_cod_database_code               7134543
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.802
_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:
 C7(H7), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C27(H27), C29(H29), C30(H30), C31(H31),
 C32(H32), C33(H33), C35(H35), C36(H36), C38(H38), C39(H39), C42(H42), C43(H43),
  C44(H44), C45(H45), C46(H46)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C40(H40A,H40B,H40C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              83754
_shelx_hkl_checksum              97663
_shelx_fab_checksum              35501
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.756