Hydrogen bonding-enabled gold catalysis: Ligand effects in gold-catalyzed cycloisomerizations in hexafluoroisopropanol (HFIP)
Nolan, Steven P.; Van Hecke, Kristof; Tzouras, Nikolaos V.; Gobbo, Alberto; Bracho, Nestor; Bhandary, Subhrajyoti; Vougioukalakis, Georgios C.; Chalkidis, Savvas; Chemical Communications  (2022) –; doi:10.1039/D2CC03056J

data_7130313
_publ_section_title
;
 Hydrogen bonding-enabled gold catalysis: Ligand effects in gold-catalyzed
 cycloisomerizations in hexafluoroisopropanol (HFIP)
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03056J
_journal_year                    2022
_chemical_formula_moiety         'C30 H37 Au F6 N2 O'
_chemical_formula_sum            'C30 H37 Au F6 N2 O'
_chemical_formula_weight         752.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.4900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.68810(10)
_cell_length_b                   16.1389(2)
_cell_length_c                   17.6877(2)
_cell_measurement_reflns_used    11376
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.7910
_cell_measurement_theta_min      3.6880
_cell_volume                     3041.66(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -86.00  -6.00   1.00    1.00    --  -41.41 125.00-180.00   80
  2  \w    -66.00  33.00   1.00    1.00    --  -41.41  38.00 120.00   99
  3  \w   -114.00 -13.00   1.00    1.00    --  -41.41 -57.00 -30.00  101
  4  \w     33.00 112.00   1.00    2.00    --  106.28-125.00 150.00   79
  5  \w     33.00 112.00   1.00    2.00    --  106.28-125.00-150.00   79
  6  \w     54.00 178.00   1.00    2.00    --  106.28  15.00 -30.00  124
  7  \w    103.00 178.00   1.00    2.00    --  106.28  77.00-150.00   75
  8  \w     33.00 132.00   1.00    2.00    --  106.28 -45.00 150.00   99
  9  \w     24.00 106.00   1.00    2.00    --  106.28 -94.00   0.00   82
 10  \w   -114.00 -13.00   1.00    1.00    --  -41.41 -57.00  60.00  101
 11  \w   -114.00 -13.00   1.00    1.00    --  -41.41 -57.00-150.00  101
 12  \w     13.00 114.00   1.00    1.00    --   41.41  57.00 150.00  101
 13  \w     77.00 178.00   1.00    2.00    --  106.28  61.00-180.00  101
 14  \w     78.00 178.00   1.00    2.00    --  106.28  30.00  60.00  100
 15  \w     97.00 178.00   1.00    2.00    --  106.28 125.00  60.00   81
 16  \w     80.00 162.00   1.00    2.00    --  106.28  45.00   0.00   82
 17  \w     78.00 178.00   1.00    2.00    --  106.28  30.00 150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1219863000
_diffrn_orient_matrix_UB_12      0.0085590000
_diffrn_orient_matrix_UB_13      0.0403242000
_diffrn_orient_matrix_UB_21      0.0732910000
_diffrn_orient_matrix_UB_22      0.0437549000
_diffrn_orient_matrix_UB_23      0.0670669000
_diffrn_orient_matrix_UB_31      -0.0255699000
_diffrn_orient_matrix_UB_32      0.0843999000
_diffrn_orient_matrix_UB_33      -0.0388442000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.840
_diffrn_reflns_theta_min         3.713
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6087
_refine_ls_number_restraints     312
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0229P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4851
_reflns_number_total             6087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03056j2.cif
_cod_data_source_block           nt474-c6d6-hex-100k
_cod_database_code               7130313
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.699
_shelx_estimated_absorpt_t_min   0.276
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2. Restrained distances
 C29A-C28 \\sim C29-C28 \\sim C28-C30 \\sim C28-C30A
 with sigma of 0.02
 F4-C30 \\sim F7A-C30A \\sim F5-C30 \\sim F5A-C30A \\sim F6A-C30A \\sim F6-C30
\\sim F3A-C29A \\sim F3-C29
 \\sim F2-C29 \\sim F2A-C29A \\sim F1A-C29A \\sim F1-C29
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim F2 \\sim F5 \\sim C28 \\sim F6 \\sim F3 \\sim F1 \\sim C29 \\sim F4
\\sim C30 \\sim C29A \\sim F3A \\sim F2A \\sim F1A \\sim C30A \\sim F7A \\sim
F6A \\sim F5A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
4. Others
 Sof(H28A)=Sof(C29A)=Sof(F3A)=Sof(F2A)=Sof(F1A)=1-FVAR(1)
 Sof(F2)=Sof(H28)=Sof(F3)=Sof(F1)=Sof(C29)=FVAR(1)
 Sof(C30A)=Sof(F7A)=Sof(F6A)=Sof(F5A)=1-FVAR(2)
 Sof(F5)=Sof(F6)=Sof(F4)=Sof(C30)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C22(H22), C28(H28), C28(H28A), C13(H13), C25(H25), C10(H10)
5.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C3(H3), C2(H2), C19(H19), C18(H18), C8(H8), C6(H6), C7(H7)
5.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C11(H11A,H11B,H11C), C26(H26A,H26B,H26C), C24(H24A,H24B,
 H24C), C12(H12A,H12B,H12C), C27(H27A,H27B,H27C), C14(H14A,H14B,H14C), C15(H15A,
 H15B,H15C)
;
_shelx_res_checksum              36638
_shelx_hkl_checksum              18851
_olex2_date_sample_data_collection 2021-11-23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.726