Inherently Chiral Homo-Heteracalixarenes: Design and Synthesis via Enantioselective Intramolecular Sonogashira Cross-coupling Reaction
Jiang, Yi-Fan Shuo; Zhang, Yue; Tong, Shuo; Zhu, Jieping; Wang, Mei-Xiang; Chemical Science  (2025) –; doi:10.1039/D5SC05923B

data_1576273
_publ_section_title
;
 Inherently Chiral Homo-Heteracalixarenes: Design and Synthesis via
 Enantioselective Intramolecular Sonogashira Cross-coupling Reaction
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC05923B
_journal_year                    2025
_chemical_formula_sum            'C40 H43 N7 O'
_chemical_formula_weight         637.81
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-10-26 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.46700(10)
_cell_length_b                   10.41070(10)
_cell_length_c                   35.2094(4)
_cell_measurement_reflns_used    12401
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0610
_cell_measurement_theta_min      2.4720
_cell_volume                     3470.17(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.134a 64-bit (release 09-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.134a (Rigaku OD, 2024)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            20029
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.593
_diffrn_reflns_theta_min         2.510
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.134a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2548 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0439
_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^+0.4092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                6486
_reflns_number_total             6946
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05923b2.cif
_cod_data_source_block           A
_cod_database_code               1576273
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              53943