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_1576272
_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            'C37 H34 N6 O5'
_chemical_formula_weight         642.70
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2lzvct
_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                80.055(2)
_cell_angle_beta                 76.924(2)
_cell_angle_gamma                82.858(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0467(2)
_cell_length_b                   11.8260(2)
_cell_length_c                   12.9432(2)
_cell_measurement_reflns_used    11342
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.6650
_cell_measurement_theta_min      3.7820
_cell_volume                     1615.87(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.952
_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  0.0313
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19809
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.709
_diffrn_reflns_theta_min         3.810
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00102(15)
_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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         6472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0359P)^2^+1.0913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5531
_reflns_number_total             6472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05923b2.cif
_cod_data_source_block           B
_cod_database_code               1576272
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              81919