Optical Resolution of 1,16-Dihydroxytetraphenylene by Chiral Gold(III) Complexation and Its Applications as Chiral Ligands in Asymmetric Catalysis
Guo, Jia; Xiong, Wen-Bin; Ma, Hao-Ran; Fan, Luoyi; Zhou, You-Yun; Wong, Henry N. C.; Cui, Jian-Fang; Chemical Science  (2022) –; doi:10.1039/D2SC00388K

data_1566701
_publ_section_title
;
 Optical Resolution of 1,16-Dihydroxytetraphenylene by Chiral Gold(III)
 Complexation and Its Applications as Chiral Ligands in Asymmetric
 Catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00388K
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H28 Au N O3, 2(C H4 O)'
_chemical_formula_sum            'C43 H40 Au N O6'
_chemical_formula_weight         863.72
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2021-12-04 deposited with the CCDC.	2022-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9306(6)
_cell_length_b                   13.2468(9)
_cell_length_c                   27.4297(18)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.53
_cell_volume                     3608.3(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            53502
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.128
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.1771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1082 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.6742.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.617
_refine_diff_density_min         -3.400
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.027(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         8989
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0003P)^2^+15.6668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                8393
_reflns_number_total             8989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00388k2.cif
_cod_data_source_block           cxy1820_0m
_cod_database_code               1566701
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.508
_shelx_estimated_absorpt_t_min   0.361
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.973(11)
 0.027(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C29A-C15A = C5A-C15A = C29-C15 = C5-C15 = C5A-C3A = C5-C3 = C37-C3 = C3A-C37A
 = C7-C37 = C7A-C37A = C7-C29 = C7A-C29A
 1.39 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C3 \\sim C7 \\sim C29 \\sim C15 \\sim C37 \\sim C5 \\sim C37A \\sim C7A \\sim
C29A \\sim C15A \\sim C5A \\sim C3A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C29) = Uanis(C29A)
Uanis(C37) = Uanis(C37A)
Uanis(C5A) = Uanis(C5)
Uanis(C15A) = Uanis(C15)
Uanis(C3) = Uanis(C3A)
Uanis(C7) = Uanis(C7A)
5. Others
 Sof(H22C)=Sof(H22D)=Sof(C37A)=Sof(C7A)=Sof(H7A)=Sof(C29A)=Sof(H29A)=Sof(C15A)=
 Sof(H15A)=Sof(C5A)=Sof(H5A)=Sof(C3A)=Sof(H3A)=1-FVAR(1)
 Sof(H22A)=Sof(H22B)=Sof(C3)=Sof(H3)=Sof(C7)=Sof(H7)=Sof(C29)=Sof(H29)=
 Sof(C15)=Sof(H15)=Sof(C37)=Sof(C5)=Sof(H5)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C24(H24)
6.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C22(H22C,H22D), C28(H28A,H28B)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C12(H12), C14(H14), C26(H26), C32(H32), C34(H34), C40(H40),
 C42(H42), C44(H44), C23(H23), C3(H3), C25(H25), C7(H7), C29(H29), C15(H15),
 C31(H31), C17(H17), C9(H9), C19(H19), C39(H39), C5(H5), C41(H41), C7A(H7A),
 C29A(H29A), C15A(H15A), C5A(H5A), C3A(H3A)
6.d Tetrahedral OH refined with riding coordinates:
 O2(H2)
6.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C33(H33A,H33B,H33C)
6.f Idealised tetrahedral OH refined as rotating group:
 O6(H6A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              46396
_shelx_hkl_checksum              58361
_shelx_fab_checksum              85928
_olex2_submission_special_instructions 'No special instructions were received'