Catalytic Asymmetric Construction of Planarly and Centrally Chiral [2.2]paracyclophanes by Merging Photochemical and Cobalt Catalyzed Desymmetrization
Zhang, Ke-Feng; Zhou, Lin-Hui; Chen, Yan-Xi; Chen, Wei-Wei; Feng, Yuan-Mei; Ma, Fang; Chemical Communications  (2025) –; doi:10.1039/D5CC03310A

data_7134813
_publ_section_title
;
 Catalytic Asymmetric Construction of Planarly and Centrally Chiral
 [2.2]paracyclophanes by Merging Photochemical and Cobalt Catalyzed
 Desymmetrization
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC03310A
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H21 Br O2'
_chemical_formula_sum            'C24 H21 Br O2'
_chemical_formula_weight         421.32
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-05-15
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-06-01 deposited with the CCDC.	2025-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                70.7830(10)
_cell_angle_beta                 77.9010(10)
_cell_angle_gamma                89.307(2)
_cell_formula_units_Z            1
_cell_length_a                   7.8150(3)
_cell_length_b                   7.9476(3)
_cell_length_c                   8.2858(3)
_cell_measurement_reflns_used    5215
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.95
_cell_measurement_theta_min      5.05
_cell_volume                     474.26(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      170.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_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       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5808
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.929
_diffrn_reflns_theta_min         5.045
_diffrn_source_current           3.57
_diffrn_source_power             0.2491146
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.093
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1553 before and 0.0842 after correction.
The Ratio of minimum to maximum transmission is 0.6228.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0859P)^2^+0.4129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.829
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                3145
_reflns_number_total             3284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03310a2.cif
_cod_data_source_block           250515zkf
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7134813
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.717
_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 O(H) groups
2. Uiso/Uaniso restraints and constraints
O2 \\sim C17 \\sim C18 \\sim C19 \\sim C24: within 2A with sigma of 0.005 and
sigma for terminal atoms of 0.01 within 2A
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C22(H22A,H22B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C11(H11), C12(H12), C17(H17),
 C20(H20), C21(H21), C24(H24)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              87282
_shelx_hkl_checksum              57291
_olex2_submission_special_instructions 'No special instructions were received'