Asymmetric Synthesis of Planar-chiral Metacyclophanes via Aromatic Amination enabled Enantioselective Desymmetrization
Zhou, Changyu; Zhou, Jinmiao; Zhang, Lele; Xie, Wansen; Gu, Huanchao; Liu, Hua; Yang, Xiaoyu; Chemical Science  (2026) –; doi:10.1039/D5SC09849A

data_1576530
_publ_section_title
;
 Asymmetric synthesis of planar-chiral metacyclophanes <i>via</i> aromatic
 amination enabled enantioselective desymmetrization.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              7582
_journal_page_last               7589
_journal_paper_doi               10.1039/d5sc09849a
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C24 H28 Cl N3 O2'
_chemical_formula_sum            'C24 H28 Cl N3 O2'
_chemical_formula_weight         425.94
_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             2025-09-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-11-06 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                78.7430(10)
_cell_angle_beta                 82.7240(10)
_cell_angle_gamma                82.149(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6243(3)
_cell_length_b                   9.9669(3)
_cell_length_c                   16.1910(5)
_cell_measurement_reflns_used    6307
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      56.77
_cell_measurement_theta_min      2.43
_cell_volume                     1344.99(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10406
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.899
_diffrn_reflns_theta_min         2.434
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           3.57
_diffrn_source_power             0.249543
_diffrn_source_target            Mo
_diffrn_source_voltage           69.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_T_max  0.3057
_exptl_absorpt_correction_T_min  0.1428
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1802 before and 0.0794 after correction.
The Ratio of minimum to maximum transmission is 0.4671.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0656
_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^)+(0.1092P)^2^+0.6957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3990
_reflns_number_total             4762
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc09849a2.cif
_cod_data_source_block           ghc_zcy_5_18_0m
_cod_depositor_comments
'Adding full bibliography for 1576529--1576530.cif.'
_cod_database_code               1576530
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00B), C00G(H00C,H00D), C00L(H00F,H00G), C00O(H00J,H00L), C00P(H00O,
 H00P), C00R(H00R,H00S), C00S(H00T,H00U), C00T(H00V,H00W), C00U(H00X,H00Y),
 C00V(H00Z,H)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), C00E(H00E), C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00M),
 C00N(H00N), C00Q(H00Q)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              42822
_shelx_fab_checksum              12227
_olex2_submission_special_instructions 'No special instructions were received'