Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable Diastereoselectivity.
Nechaev, Anton A.; Van Hecke, Kristof; Zaman, Manzoor; Kashtanov, Stepan; Ungur, Liviu; Pereshivko, Olga P.; Peshkov, Vsevolod A.; Van der Eycken, Erik V.; The Journal of organic chemistry 83 (2018) 8170–8182; doi:10.1021/acs.joc.8b00953

data_4035573
_publ_section_title
;
 Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable
 Diastereoselectivity.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8170
_journal_page_last               8182
_journal_paper_doi               10.1021/acs.joc.8b00953
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H22 N2 O3'
_chemical_formula_sum            'C21 H22 N2 O3'
_chemical_formula_weight         350.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-09-13
_audit_creation_method
;
Olex2 1.2
(compiled Aug 10 2017 17:28:52 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                108.812(3)
_cell_angle_beta                 101.750(3)
_cell_angle_gamma                103.021(3)
_cell_formula_units_Z            4
_cell_length_a                   12.9746(5)
_cell_length_b                   13.3439(5)
_cell_length_c                   13.6301(5)
_cell_measurement_reflns_used    17073
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.3700
_cell_measurement_theta_min      3.5550
_cell_volume                     2076.35(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_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 0.980
_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   -117.00 -17.00   1.00    2.00    --  -41.68 -35.00 -93.00  100
  2  \w    -67.00  33.00   1.00    2.00    --  -41.68  35.00  63.00  100
  3  \w    -33.00  67.00   1.00    2.00    --   41.68 -35.00 -93.00  100
  4  \w     17.00 117.00   1.00    2.00    --   41.68  35.00  63.00  100
  5  \w     34.00 134.00   1.00   15.00    --  109.13 -35.00 -93.00  100
  6  \w     84.00 178.00   1.00   15.00    --  109.13  35.00  63.00   94
  7  \w    -96.00  -2.00   1.00    2.00    --  -41.68 125.00  60.00   94
  8  \w    -96.00  -2.00   1.00    2.00    --  -41.68 125.00 150.00   94
  9  \w     23.00  98.00   1.00    2.00    --   41.68-125.00 -60.00   75
 10  \w     33.00 137.00   1.00   15.00    --  109.13 -30.00  60.00  104
 11  \w     94.00 178.00   1.00   15.00    --  109.13 125.00   0.00   84
 12  \w     81.00 178.00   1.00   15.00    --  109.13  30.00 120.00   97
 13  \w     36.00 121.00   1.00   15.00    --  109.13-125.00 120.00   85
 14  \w     94.00 178.00   1.00   15.00    --  109.13 125.00 150.00   84
 15  \w     36.00 121.00   1.00   15.00    --  109.13-125.00-120.00   85
 16  \w     83.00 178.00   1.00   15.00    --  109.13  45.00 -30.00   95
 17  \w     26.00 109.00   1.00   15.00    --  109.13 -94.00 -60.00   83
 18  \w     26.00 109.00   1.00   15.00    --  109.13 -94.00 150.00   83
 19  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00-120.00  101
 20  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00-180.00  109
 21  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00 -30.00  109
 22  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00-120.00  109
 23  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00  90.00  109
 24  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00  60.00  109
 25  \w     81.00 178.00   1.00   15.00    --  109.13  30.00-120.00   97
 26  \w     80.00 178.00   1.00   15.00    --  109.13  61.00-120.00   98
 27  \w     80.00 178.00   1.00   15.00    --  109.13  61.00-180.00   98
 28  \w     80.00 178.00   1.00   15.00    --  109.13  61.00 120.00   98
 29  \w     80.00 178.00   1.00   15.00    --  109.13  61.00   0.00   98
 30  \w     80.00 178.00   1.00   15.00    --  109.13  61.00 -90.00   98
 31  \w     80.00 178.00   1.00   15.00    --  109.13  61.00  60.00   98
 32  \w     80.00 178.00   1.00   15.00    --  109.13  61.00 -60.00   98
 33  \w     77.00 178.00   1.00   15.00    --  109.13  77.00   0.00  101
 34  \w     80.00 178.00   1.00   15.00    --  109.13  61.00 -30.00   98
 35  \w     80.00 178.00   1.00   15.00    --  109.13  61.00  90.00   98
 36  \w     81.00 178.00   1.00   15.00    --  109.13  30.00-180.00   97
 37  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00 120.00  109
 38  \w   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00 -30.00   99
 39  \w   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00-120.00   99
 40  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00-150.00  101
 41  \w   -118.00  -9.00   1.00    2.00    --  -41.68 -77.00  30.00  109
 42  \w   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 -90.00  101
 43  \w     80.00 128.00   1.00   15.00    --  109.13  61.00-150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0193860000
_diffrn_orient_matrix_UB_12      -0.0815892000
_diffrn_orient_matrix_UB_13      0.0546428000
_diffrn_orient_matrix_UB_21      -0.1250939000
_diffrn_orient_matrix_UB_22      -0.0415071000
_diffrn_orient_matrix_UB_23      -0.0145532000
_diffrn_orient_matrix_UB_31      -0.0171040000
_diffrn_orient_matrix_UB_32      -0.0901277000
_diffrn_orient_matrix_UB_33      -0.1116502000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            51210
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.487
_diffrn_reflns_theta_min         3.591
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         8446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0618P)^2^+0.2696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6506
_reflns_number_total             8446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00953_si_005.cif
_cod_data_source_block           evde_ugent008_sq
_cod_database_code               4035573
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C21 H22 N2 O3'
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.890
_reflns_odcompleteness_completeness 100.00
_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 O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C23(H23), C27(H27), C2(H2A), C24(H24), C16(H16), C3(H3),
 C8(H8), C26(H26), C37(H37), C33(H33), C12(H12), C29(H29), C7(H7), C15(H15),
 C13(H13), C36(H36), C28(H28), C14(H14), C35(H35), C34(H34)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C42(H42A,H42B,H42C), C41(H41A,H41B,H41C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              488
_shelx_hkl_checksum              66896
_shelx_fab_checksum              3595
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 1.882
_oxdiff_exptl_absorpt_empirical_full_min 0.809