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_1566705
_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            'C42 H36 Au N O5'
_chemical_formula_weight         831.68
_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             2021-10-22
_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                   9.9266(7)
_cell_length_b                   13.1669(9)
_cell_length_c                   27.3976(19)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.53
_cell_volume                     3580.9(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 2014/5 (Sheldrick, 2014)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_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  0.0994
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            84689
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.534
_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    4.154
_exptl_absorpt_correction_T_max  0.0468
_exptl_absorpt_correction_T_min  0.0193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1083 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.4124.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         2.530
_refine_diff_density_min         -3.120
_refine_diff_density_rms         0.167
_refine_ls_abs_structure_details
;
 Flack x determined using 2909 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(4)
_refine_ls_extinction_coef       0.0012(2)
_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   1.260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8230
_refine_ls_number_restraints     221
_refine_ls_restrained_S_all      1.243
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0432P)^2^+18.0763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                7593
_reflns_number_total             8230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00388k2.cif
_cod_data_source_block           cxy1814_0m
_cod_database_code               1566705
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.423
_shelx_estimated_absorpt_t_min   0.350
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C27-C28 \\sim C27-C28A
 with sigma of 0.02
 C33-C29 \\sim C33A-C29A
 with sigma of 0.04
 C28-C29 \\sim C28A-C29A
 with sigma of 0.02
 C31-C33 \\sim C31A-C33A
 with sigma of 0.04
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 C30-C29 \\sim C30A-C29A
 with sigma of 0.02
 C34-C32 \\sim C34A-C32A
 with sigma of 0.04
 C31-C32 \\sim C31A-C32A
 with sigma of 0.02
 C33-C34 \\sim C33A-C34A
 with sigma of 0.02
 C33-C32 \\sim C33A-C32A
 with sigma of 0.02
 C34-C29 \\sim C34A-C29A
 with sigma of 0.02
 C31-C29 \\sim C31A-C29A
 with sigma of 0.04
 C27-C29 \\sim C27-C29A
 with sigma of 0.04
 C28-C30 \\sim C28A-C30A
 with sigma of 0.04
 C28-C34 \\sim C28A-C34A
 with sigma of 0.04
 C30-C34 \\sim C30A-C34A
 with sigma of 0.04
 C30-C32 \\sim C30A-C32A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C28 \\sim C30 \\sim C31 \\sim C33 \\sim C34 \\sim C29 \\sim C32 \\sim C28A
\\sim C29A \\sim C34A \\sim C33A \\sim C32A \\sim C31A \\sim C30A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C31A) = Uanis(C31)
Uanis(C29A) = Uanis(C29)
Uanis(C33A) = Uanis(C33)
Uanis(C28A) = Uanis(C28)
Uanis(C34A) = Uanis(C34)
Uanis(C32A) = Uanis(C32)
Uanis(C30) = Uanis(C30A)
4. Others
 Sof(H27A)=Sof(C28A)=Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(C34A)=Sof(H34A)=
 Sof(C33A)=Sof(H33A)=Sof(C32A)=Sof(H32A)=Sof(C31A)=Sof(H31A)=Sof(C30A)=
 Sof(H30A)=1-FVAR(1)
 Sof(H27)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=
 Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C29)=Sof(C32)=Sof(H32)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C27(H27), C27(H27A)
5.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C26(H26A,H26B), C28A(H28C,H28D)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C6(H6), C16(H16), C38(H38), C30(H30), C24(H24), C14(H14),
 C15(H15), C21(H21), C31(H31), C19(H19), C20(H20), C37(H37), C23(H23), C39(H39),
  C33(H33), C34(H34), C40(H40), C18(H18), C17(H17), C32(H32), C22(H22),
 C34A(H34A), C33A(H33A), C32A(H32A), C31A(H31A), C30A(H30A)
5.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5A)
;
_shelx_res_checksum              20217
_shelx_hkl_checksum              97252
_olex2_submission_special_instructions 'No special instructions were received'