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_7134542
_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         '8(C34 H32 N2 O5 S)'
_chemical_formula_sum            'C272 H256 N16 O40 S8'
_chemical_formula_weight         4645.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-07-31 deposited with the CCDC.	2025-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.3130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   5.68660(10)
_cell_length_b                   20.2872(3)
_cell_length_c                   48.7011(7)
_cell_measurement_reflns_used    20746
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4890
_cell_measurement_theta_min      3.6360
_cell_volume                     5609.02(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (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-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_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     24.00  55.00   0.50    6.80    --   56.05 -95.00  90.00   62
  2  \w     25.00  51.00   0.50    6.80    --   56.05 -95.00 150.00   52
  3  \w     15.00  54.00   0.50    6.80    --   56.05 -95.00   0.00   78
  4  \w     25.00  51.00   0.50    6.80    --   56.05 -95.00-120.00   52
  5  \w     60.00  86.00   0.50    6.80    --   56.05  15.00  60.00   52
  6  \w     18.00  50.00   0.50    6.80    --   56.05 -95.00 -60.00   64
  7  \w     25.00  51.00   0.50    6.80    --   56.05-125.00-120.00   52
  8  \w    -83.00 -33.00   0.50    6.80    --  -59.24 -15.00-120.00  100
  9  \w    -59.00 -26.00   0.50    6.80    --  -59.24 125.00  30.00   66
 10  \w    -69.00 -26.00   0.50    6.80    --  -71.82 125.00-180.00   86
 11  \w    -92.00 -31.00   0.50    6.80    --  -75.32 111.00   0.00  122
 12  \w   -125.00 -50.00   0.50    6.80    --  -75.32 -15.00  90.00  150
 13  \w   -125.00 -40.00   0.50    6.80    --  -75.32 -15.00   0.00  170
 14  \w     43.00  69.00   0.50    6.80    --   75.94-111.00-120.00   52
 15  \w     40.00 117.00   0.50    6.80    --   75.94  15.00 -60.00  154
 16  \w     36.00  65.00   0.50    6.80    --   75.94 -95.00 -60.00   58
 17  \w     39.00  84.00   0.50    6.80    --   75.94 -95.00 -30.00   90
 18  \w     32.00  92.00   0.50    6.80    --   75.94-111.00-150.00  120
 19  \w     40.00 119.00   0.50    6.80    --   75.94  15.00  30.00  158
 20  \w     39.00  84.00   0.50    6.80    --   75.94 -95.00 -90.00   90
 21  \w    -97.00 -32.00   0.50    6.80    --  -78.00 114.00  74.19  130
 22  \w     41.00  91.00   0.50    6.80    --   83.87 -95.00-180.00  100
 23  \w     63.00 132.00   0.50    6.80    --   83.87  15.00-150.00  138
 24  \w     49.00  93.00   0.50    6.80    --   83.87  15.00-180.00   88
 25  \w     65.00  92.00   0.50    6.80    --   83.87 -95.00 -60.00   54
 26  \w     54.00  92.00   0.50    6.80    --   83.87 -95.00-120.00   76
 27  \w     53.00 102.00   0.50    6.80    --   83.87  15.00 -30.00   98
 28  \w     46.00  92.00   0.50    6.80    --   83.87 -95.00   0.00   92
 29  \w     65.00  90.00   0.50    6.80    --   83.87 -95.00-150.00   50
 30  \w     39.00  68.00   0.50    6.80    --   83.87-111.00  90.00   58
 31  \w     44.00  69.00   0.50    6.80    --   83.87-111.00   0.00   50
 32  \w     66.00  92.00   0.50    6.80    --   83.87 -95.00 120.00   52
 33  \w     65.00  92.00   0.50    6.80    --   83.87 -95.00  60.00   54
 34  \w     41.00  90.00   0.50    6.80    --   83.87 -95.00 150.00   98
 35  \w     55.00 128.00   0.50    6.80    --   83.87  15.00  90.00  146
 36  \w     41.00  66.00   0.50    6.80    --   83.87 -95.00  90.00   50
;
_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      0.0012351500
_diffrn_orient_matrix_UB_12      0.0747459500
_diffrn_orient_matrix_UB_13      -0.0055607000
_diffrn_orient_matrix_UB_21      0.0048889000
_diffrn_orient_matrix_UB_22      0.0133782000
_diffrn_orient_matrix_UB_23      0.0311725000
_diffrn_orient_matrix_UB_31      0.2712833000
_diffrn_orient_matrix_UB_32      -0.0005956000
_diffrn_orient_matrix_UB_33      0.0013140000
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       60
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_number            33611
_diffrn_reflns_point_group_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.012
_diffrn_reflns_theta_min         1.817
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (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    1.375
_exptl_crystal_description       needle
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 2508 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     763
_refine_ls_number_reflns         8552
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0462P)^2^+9.2593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_full    0.570
_reflns_Friedel_fraction_max     0.511
_reflns_number_gt                7935
_reflns_number_total             8552
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00353a2.cif
_cod_data_source_block           230803lt
_cod_depositor_comments
'Adding full bibliography for 7134542--7134544.cif.'
_cod_database_code               7134542
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.883
_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:
 C10(H10), C12(H12), C22(H22), C44(H44), C46(H46), C56(H56)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C45(H45A,H45B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C16(H16), C17(H17), C19(H19), C20(H20),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34), C36(H36), C37(H37), C39(H39), C40(H40), C50(H50),
 C51(H51), C53(H53), C54(H54), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62),
  C64(H64), C65(H65), C66(H66), C67(H67), C68(H68)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C21(H21A,H21B,H21C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C), C55(H55A,H55B,H55C)
;
_shelx_res_checksum              77265
_shelx_hkl_checksum              44461
_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 2.090
_oxdiff_exptl_absorpt_empirical_full_min 0.633