Enantioselective gold(I)-catalysed alkyne hydroarylations for inherently chiral calix[4]arenes.
Goudarzi, Mehri; Alagiyawanna, Anuruddha; Serafino, Andrea; Rizzato, Silvia; Bertocchi, Francesco; Terenziani, Francesca; Santoro, Stefano; Qin, Wenling; Cera, Gianpiero; Pirovano, Valentina; Chemical communications (Cambridge, England) 61 (2025) 16380–16383; doi:10.1039/d5cc04405g

data_1575725
_publ_section_title
;
 Enantioselective gold(I)-catalysed alkyne hydroarylations for inherently
 chiral calix[4]arenes.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16380
_journal_page_last               16383
_journal_paper_doi               10.1039/d5cc04405g
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C48 H51 Cl O4'
_chemical_formula_sum            'C48 H51 Cl O4'
_chemical_formula_weight         727.34
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2025-07-28 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3490(1)
_cell_length_b                   9.5621(1)
_cell_length_c                   44.4373(5)
_cell_measurement_reflns_used    31072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.709
_cell_measurement_theta_min      3.945
_cell_measurement_wavelength     1.54184
_cell_volume                     3972.52(7)
_computing_data_collection       'CrysAlis PRO; Rigaku OD, 2023'
_computing_data_reduction        'CrysAlis PRO; Rigaku OD, 2023'
_computing_molecular_graphics    'VESTA 3(Momma et al., 2011)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.2(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     35.00 126.00   0.50    0.05    --   53.69  71.00 -31.00  182
  2  \w     35.00 126.00   0.50    0.05    --   53.69  71.00 -31.00  182
  3  \w     32.00 126.00   0.50    0.05    --   53.69  77.00  60.00  188
  4  \w     32.00 126.00   0.50    0.05    --   53.69  77.00  60.00  188
  5  \w    -20.00  72.00   0.50    0.05    --   -0.47  71.00 -31.00  184
  6  \w    -44.00  18.00   0.50    0.05    --  -54.62  38.00-120.00  124
  7  \w    -44.00  18.00   0.50    0.05    --  -54.62  38.00-120.00  124
  8  \w    -74.00  18.00   0.50    0.05    --  -54.62  71.00 -31.00  184
  9  \w    -27.00  20.00   0.50    0.05    --  -54.62  19.00 120.00   94
 10  \w    -86.00 -13.00   0.50    0.05    --  -54.62 125.00   0.00  146
 11  \w    -86.00 -13.00   0.50    0.05    --  -54.62 125.00 -30.00  146
 12  \w    -86.00 -13.00   0.50    0.05    --  -54.62 125.00-120.00  146
 13  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00-180.00  186
 14  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00-120.00  186
 15  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 -90.00  186
 16  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 -90.00  186
 17  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 -30.00  186
 18  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 -30.00  186
 19  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00-120.00  186
 20  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00  30.00  186
 21  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00  90.00  186
 22  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 150.00  186
 23  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 150.00  186
 24  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 120.00  186
 25  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00  90.00  186
 26  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 -60.00  186
 27  \w   -126.00 -35.00   0.50    0.05    --  -54.62 -71.00-162.00  182
 28  \w   -126.00 -35.00   0.50    0.05    --  -54.62 -71.00-162.00  182
 29  \w   -126.00 -33.00   0.50    0.05    --  -54.62 -77.00 -60.00  186
 30  \w    -73.00  19.00   0.50    0.05    --   -0.47 -71.00-162.00  184
 31  \w    -73.00  14.00   0.50    0.05    --   -0.47 -57.00 -90.00  174
 32  \w    -18.00  73.00   0.50    0.05    --   53.69 -71.00-162.00  182
 33  \w     34.00 100.00   0.50    0.05    --   53.69-125.00-180.00  132
 34  \w     -1.00  86.00   0.50    0.05    --   53.69 -99.00-180.00  174
 35  \w    -18.00  73.00   0.50    0.05    --   53.69 -71.00-162.00  182
 36  \w     34.00 100.00   0.50    0.05    --   53.69-125.00   0.00  132
 37  \w     34.00 100.00   0.50    0.05    --   53.69-125.00   0.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0205813000
_diffrn_orient_matrix_UB_12      -0.1590883000
_diffrn_orient_matrix_UB_13      0.0033285000
_diffrn_orient_matrix_UB_21      0.1017056000
_diffrn_orient_matrix_UB_22      -0.0002788000
_diffrn_orient_matrix_UB_23      0.0272723000
_diffrn_orient_matrix_UB_31      -0.1279771000
_diffrn_orient_matrix_UB_32      0.0254183000
_diffrn_orient_matrix_UB_33      0.0211532000
_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  0.0543
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            83139
_diffrn_reflns_theta_full        51.911
_diffrn_reflns_theta_max         51.911
_diffrn_reflns_theta_min         3.979
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.116a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1552
_exptl_crystal_recrystallization_method
'crystallization by slow evaporation from a mixed   n-hexane/isopropanol solution (99.5:0.5, v/v) solution'
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1646 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(8)
_refine_ls_extinction_coef       0.00041(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     479
_refine_ls_number_reflns         4424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+3.1615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4261
_reflns_number_total             4424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04405g2.cif
_cod_data_source_block           2k
_cod_depositor_comments
'Adding full bibliography for 1575724--1575725.cif.'
_cod_database_code               1575725
_oxdiff_exptl_absorpt_empirical_full_min 0.745
_oxdiff_exptl_absorpt_empirical_full_max 1.474
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;