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_1566704
_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 H2 Cl2)'
_chemical_formula_sum            'C42 H32 Au Cl4 N O3'
_chemical_formula_weight         937.45
_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             2021-04-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_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                   12.5780(10)
_cell_length_b                   13.7123(11)
_cell_length_c                   21.0398(15)
_cell_measurement_reflns_used    9497
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.40
_cell_volume                     3628.8(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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  (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 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  0.0524
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            70184
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.443
_diffrn_reflns_theta_min         2.197
_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    4.391
_exptl_absorpt_correction_T_max  0.0962
_exptl_absorpt_correction_T_min  0.0508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1121 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.5281.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_description       block
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         5.102
_refine_diff_density_min         -4.560
_refine_diff_density_rms         0.200
_refine_ls_abs_structure_details
;
 Flack x determined using 3785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         9114
_refine_ls_number_restraints     243
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0325P)^2^+45.8527P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                8909
_reflns_number_total             9114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00388k2.cif
_cod_data_source_block           cxy1677_0m
_cod_database_code               1566704
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C33-C31 \\sim C33A-C31A
 with sigma of 0.04
 C29-C28 \\sim C29A-C28
 with sigma of 0.02
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 C34-C32 \\sim C34A-C32A
 with sigma of 0.04
 C29-C30 \\sim C29A-C30A
 with sigma of 0.02
 C29-C34 \\sim C29A-C34A
 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
 C30-C32 \\sim C30A-C32A
 with sigma of 0.04
 C29-C33 \\sim C29A-C33A
 with sigma of 0.04
 C29-C31 \\sim C29A-C31A
 with sigma of 0.04
 C31-C32 \\sim C31A-C32A
 with sigma of 0.02
 C28-C30 \\sim C28-C30A
 with sigma of 0.04
 C28-C34 \\sim C28-C34A
 with sigma of 0.04
 C30-C34 \\sim C30A-C34A
 with sigma of 0.04
3. Restrained planarity
 C29A, C34A, C33A, C32A, C31A, C30A
 with sigma of 0.1
 C29, C34, C33, C32, C31, C30
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C29: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C29 \\sim C30 \\sim C33 \\sim C31 \\sim C34 \\sim C32 \\sim C29A \\sim C30A
\\sim C31A \\sim C32A \\sim C33A \\sim C34A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
Uanis(C31) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C29) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C32)
\\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C34) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl2) = Uanis(Cl3)
Uanis(C33) = Uanis(C33A)
Uanis(C29A) = Uanis(C29)
Uanis(C31) = Uanis(C31A)
Uanis(C30A) = Uanis(C30)
Uanis(C32) = Uanis(C32A)
Uanis(C34) = Uanis(C34A)
5. Others
 Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=
 Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34A)=1-FVAR(1)
 Sof(C29)=Sof(H28A)=Sof(H28B)=Sof(C30)=Sof(H30)=Sof(C33)=Sof(H33)=Sof(C31)=
 Sof(H31)=Sof(C34)=Sof(H34)=Sof(C32)=Sof(H32)=FVAR(1)
 Fixed Sof: Cl2(0.605) Cl3(0.395) H41A(0.605) H41B(0.605) H41C(0.395)
 H41D(0.395)
6.a Ternary CH refined with riding coordinates:
 C27(H27)
6.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C28(H28C,H28D), C26(H26A,H26B), C41(H41A,H41B), C41(H41C,
 H41D), C42(H42A,H42B)
6.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C37(H37), C5(H5), C30(H30), C33(H33), C18(H18), C6(H6), C16(H16),
 C19(H19), C20(H20), C40(H40), C22(H22), C15(H15), C31(H31), C23(H23), C34(H34),
  C38(H38), C24(H24), C39(H39), C32(H32), C7(H7), C21(H21), C14(H14),
 C30A(H30A), C31A(H31A), C32A(H32A), C33A(H33A), C34A(H34A)
;
_shelx_res_checksum              39734
_shelx_hkl_checksum              91759
_olex2_submission_special_instructions 'No special instructions were received'