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_4035571
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-12
_audit_creation_method
;
Olex2 1.2
(compiled Aug 10 2017 17:28:52 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.15169(16)
_cell_length_b                   16.2452(2)
_cell_length_c                   24.9550(3)
_cell_measurement_reflns_used    28166
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.3120
_cell_measurement_theta_min      3.4980
_cell_volume                     3710.09(9)
_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)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_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 0.992
_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    -76.00  38.00   1.00    2.00    --  -41.80  84.00 100.00  114
  2  \w     98.00 178.00   1.00   10.00    --  109.13 118.00 177.00   80
  3  \w     98.00 178.00   1.00   10.00    --  109.13  84.00 100.00   80
  4  \w     35.00 134.00   1.00   10.00    --  109.13 -39.00 161.00   99
  5  \w   -114.00 -14.00   1.00    2.00    --  -41.80 -57.00 -90.00  100
  6  \w   -116.00 -17.00   1.00    2.00    --  -41.80 -38.00-150.00   99
  7  \w     72.00 118.00   1.00    2.00    --   41.80 160.00 -29.00   46
  8  \w     26.00 109.00   1.00   10.00    --  109.13 -94.00 -60.00   83
  9  \w     33.00 142.00   1.00   10.00    --  109.13 -77.00  90.00  109
 10  \w     33.00 137.00   1.00   10.00    --  109.13 -30.00 -60.00  104
 11  \w   -114.00 -14.00   1.00    2.00    --  -41.80 -57.00  30.00  100
 12  \w   -116.00 -17.00   1.00    2.00    --  -41.80 -38.00 120.00   99
 13  \w      1.00  83.00   1.00    2.00    --   41.80 -99.00   0.00   82
 14  \w     56.00 178.00   1.00   10.00    --  109.13  15.00-120.00  122
 15  \w     81.00 178.00   1.00   10.00    --  109.13  30.00  60.00   97
 16  \w     80.00 178.00   1.00   10.00    --  109.13  61.00 -90.00   98
 17  \w     83.00 178.00   1.00   10.00    --  109.13  45.00   0.00   95
 18  \w     81.00 178.00   1.00   10.00    --  109.13  30.00 120.00   97
 19  \w     81.00 178.00   1.00   10.00    --  109.13  30.00 -30.00   97
 20  \w   -118.00  -9.00   1.00    2.00    --  -41.80 -77.00-150.00  109
 21  \w   -118.00  -9.00   1.00    2.00    --  -41.80 -77.00   0.00  109
 22  \w   -118.00  -9.00   1.00    2.00    --  -41.80 -77.00 120.00  109
 23  \w     80.00 178.00   1.00   10.00    --  109.13  61.00-120.00   98
 24  \w     77.00 178.00   1.00   10.00    --  109.13  77.00 120.00  101
 25  \w     80.00 178.00   1.00   10.00    --  109.13  61.00  60.00   98
 26  \w     77.00 178.00   1.00   10.00    --  109.13  77.00 150.00  101
 27  \w     80.00 178.00   1.00   10.00    --  109.13  61.00-150.00   98
 28  \w     26.00 109.00   1.00   10.00    --  109.13 -94.00-180.00   83
 29  \w   -118.00  -9.00   1.00    2.00    --  -41.80 -77.00 -90.00  109
 30  \w     23.00  98.00   1.00    2.00    --   41.80-125.00-180.00   75
 31  \w      1.00  83.00   1.00    2.00    --   41.80 -99.00-120.00   82
 32  \w     80.00 142.00   1.00   10.00    --  109.13  61.00   0.00   62
 33  \w     83.00 178.00   1.00   10.00    --  109.13  45.00 -30.00   95
;
_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      -0.0421358000
_diffrn_orient_matrix_UB_12      -0.0646680000
_diffrn_orient_matrix_UB_13      -0.0424245000
_diffrn_orient_matrix_UB_21      -0.0702992000
_diffrn_orient_matrix_UB_22      -0.0534420000
_diffrn_orient_matrix_UB_23      0.0439940000
_diffrn_orient_matrix_UB_31      -0.1470067000
_diffrn_orient_matrix_UB_32      0.0441575000
_diffrn_orient_matrix_UB_33      -0.0088954000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            66552
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.548
_diffrn_reflns_theta_min         3.542
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.974
_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    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0585P)^2^+1.2308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3433
_reflns_number_total             3826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00953_si_004.cif
_cod_data_source_block           evde_ugent007
_cod_database_code               4035571
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C21 H22 N2 O3'
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.858
_reflns_odcompleteness_completeness 99.95
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
  C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              43529
_shelx_hkl_checksum              75964
_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 1.944
_oxdiff_exptl_absorpt_empirical_full_min 0.698