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_4035572
_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         'C22 H24 N2 O3'
_chemical_formula_sum            'C22 H24 N2 O3'
_chemical_formula_weight         364.43
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-18
_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                 94.685(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6066(4)
_cell_length_b                   11.2438(2)
_cell_length_c                   22.0936(5)
_cell_measurement_reflns_used    14685
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      66.9650
_cell_measurement_theta_min      3.9810
_cell_volume                     3863.98(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)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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    -74.00  36.00   1.00    2.00    --  -41.80  25.00-161.00  110
  2  \w   -120.00  -9.00   1.00    2.00    --  -41.80 -25.00  34.00  111
  3  \w    -36.00  74.00   1.00    2.00    --   41.80 -25.00  34.00  110
  4  \w      9.00 120.00   1.00    2.00    --   41.80  25.00-161.00  111
  5  \w     31.00 141.00   1.00   10.00    --  109.13 -25.00  34.00  110
  6  \w     77.00 178.00   1.00   10.00    --  109.13  25.00-161.00  101
  7  \w     23.00  98.00   1.00    2.00    --   41.80-125.00 -90.00   75
  8  \w     23.00  98.00   1.00    2.00    --   41.80-125.00 150.00   75
  9  \w     83.00 178.00   1.00   10.00    --  109.13  45.00  90.00   95
 10  \w     94.00 178.00   1.00   10.00    --  109.13 125.00  60.00   84
 11  \w     36.00 135.00   1.00   10.00    --  109.13 -45.00 120.00   99
 12  \w     26.00 109.00   1.00   10.00    --  109.13 -94.00  90.00   83
 13  \w     26.00 109.00   1.00   10.00    --  109.13 -94.00 -30.00   83
 14  \w     26.00 109.00   1.00   10.00    --  109.13 -94.00   0.00   83
 15  \w     14.00 115.00   1.00    2.00    --   41.80  57.00  30.00  101
 16  \w      9.00 118.00   1.00    2.00    --   41.80  77.00-180.00  109
 17  \w      9.00 111.00   1.00    2.00    --   41.80  77.00  90.00  102
 18  \w      9.00 118.00   1.00    2.00    --   41.80  77.00 -90.00  109
;
_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      0.0974625000
_diffrn_orient_matrix_UB_12      -0.0201847000
_diffrn_orient_matrix_UB_13      0.0127890000
_diffrn_orient_matrix_UB_21      -0.0053599000
_diffrn_orient_matrix_UB_22      0.0409314000
_diffrn_orient_matrix_UB_23      0.0661587000
_diffrn_orient_matrix_UB_31      -0.0168020000
_diffrn_orient_matrix_UB_32      -0.1291166000
_diffrn_orient_matrix_UB_33      0.0189685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34143
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.476
_diffrn_reflns_theta_min         4.015
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.976
_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    1.253
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         6911
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.8731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5726
_reflns_number_total             6911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00953_si_003.cif
_cod_data_source_block           evde_ugent010
_cod_database_code               4035572
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C22 H24 N2 O3'
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.852
_reflns_odcompleteness_completeness 99.89
_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
 N4-H4 = N2-H2
 0.88 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C11(H11), C33(H33)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32), C35(H35),
  C36(H36), C37(H37), C38(H38), C39(H39)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C27(H27A,H27B,H27C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,
 H44B,H44C)
;
_shelx_res_checksum              85785
_shelx_hkl_checksum              66053
_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 2.360
_oxdiff_exptl_absorpt_empirical_full_min 0.748