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_1566703
_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, 1.167(C H Cl3)'
_chemical_formula_sum            'C41.17 H29.17 Au Cl3.5 N O3'
_chemical_formula_weight         906.87
_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             2021-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_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                   12.999(5)
_cell_length_b                   13.954(4)
_cell_length_c                   22.150(8)
_cell_measurement_reflns_used    8353
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      2.33
_cell_volume                     4018(2)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_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 0.997
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.336
_diffrn_reflns_theta_min         2.330
_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    3.931
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0961 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.6587.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             1783
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.199
_refine_diff_density_min         -0.983
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details
;
 Flack x determined using 2636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         9044
_refine_ls_number_restraints     270
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0747P)^2^+3.6438P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7090
_reflns_number_total             9044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00388k2.cif
_cod_data_source_block           cxy1846_0m
_cod_original_formula_sum        'C41.17 H29.17 Au Cl3.50 N O3'
_cod_database_code               1566703
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2-Cl3 = C2-Cl4 = C2-Cl5
 1.78 with sigma of 0.02
 C1-Cl1 = C1-Cl2 = C1-Cl6
 1.78 with sigma of 0.02
 C1A-Cl7 = C1A-Cl8 = C1A-Cl9
 1.78 with sigma of 0.02
 C1B-Cl10 = C1B-Cl11 = C1B-Cl12
 1.78 with sigma of 0.02
 Cl1-Cl2 \\sim Cl2-Cl6 \\sim Cl6-Cl1
 with sigma of 0.04
 C2-Cl3 \\sim C2-Cl4 \\sim C2-Cl5
 with sigma of 0.02
 Cl3-Cl4 \\sim Cl4-Cl5 \\sim Cl5-Cl3
 with sigma of 0.04
 C1-Cl1 \\sim C1-Cl2 \\sim C1-Cl6
 with sigma of 0.02
 C1A-Cl7 \\sim C1A-Cl8 \\sim C1A-Cl9
 with sigma of 0.02
 Cl7-Cl8 \\sim Cl8-Cl9 \\sim Cl9-Cl7
 with sigma of 0.04
 Cl10-Cl11 \\sim Cl11-Cl12 \\sim Cl12-Cl10
 with sigma of 0.04
 C1B-Cl10 \\sim C1B-Cl11 \\sim C1B-Cl12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C2 \\sim Cl3 \\sim Cl4 \\sim Cl5: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C1 \\sim Cl1 \\sim Cl2 \\sim Cl6: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C1A \\sim Cl7 \\sim Cl8 \\sim Cl9: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C1B \\sim Cl10 \\sim Cl11 \\sim Cl12: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C2 \\sim Cl3 \\sim Cl4 \\sim Cl5 \\sim C1B \\sim Cl10 \\sim Cl11 \\sim Cl12:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Cl2 \\sim C1 \\sim Cl1 \\sim Cl6 \\sim C1A \\sim Cl7 \\sim Cl8 \\sim Cl9:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C2, Cl3, Cl4, Cl5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, Cl1, Cl2, Cl6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1A, Cl7, Cl8, Cl9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1B, Cl10, Cl11, Cl12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C2(0.33333) H2(0.33333) Cl3(0.33333) Cl4(0.33333) Cl5(0.33333)
 C1(0.33333) H1(0.33333) Cl1(0.33333) Cl2(0.33333) Cl6(0.33333) C1A(0.25)
 H1A(0.25) Cl7(0.25) Cl8(0.25) Cl9(0.25) C1B(0.25) H1B(0.25) Cl10(0.25)
 Cl11(0.25) Cl12(0.25)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2), C1(H1), C1A(H1A), C1B(H1B)
6.b Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB), C12(H12A,H12B)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C23(H23), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31),
  C33(H33), C34(H34), C35(H35), C36(H36), C39(H39), C40(H40), C41(H41)
;
_shelx_res_checksum              14813
_shelx_hkl_checksum              27795
_olex2_submission_special_instructions 'No special instructions were received'