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_4035570
_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_absolute_configuration ad
_chemical_formula_moiety         'C24 H28 N2 O3'
_chemical_formula_sum            'C24 H28 N2 O3'
_chemical_formula_weight         392.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 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                 113.578(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4719(4)
_cell_length_b                   24.5538(10)
_cell_length_c                   9.7594(5)
_cell_measurement_reflns_used    8117
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.2930
_cell_measurement_theta_min      3.4520
_cell_volume                     2080.27(19)
_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 0.989
_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    -70.00  31.00   1.00    1.00    --  -41.80  59.00-120.00  101
  2  \w    -55.00 -13.00   1.00    1.00    --  -41.80 -59.00  99.00   42
  3  \w     36.00 138.00   1.00    1.50    --  109.13 -59.00  99.00  102
  4  \w     80.00 178.00   1.00    1.50    --  109.13  59.00-120.00   98
  5  \w      1.00  83.00   1.00    1.00    --   41.80 -99.00  90.00   82
  6  \w     23.00  98.00   1.00    1.00    --   41.80-125.00   0.00   75
  7  \w    102.00 115.00   1.00    1.00    --   41.80  59.00-120.00   13
  8  \w     81.00 178.00   1.00    1.50    --  109.13  30.00 -30.00   97
  9  \w     37.00 138.00   1.00    1.50    --  109.13 -61.00 -30.00  101
 10  \w     94.00 178.00   1.00    1.50    --  109.13 125.00  30.00   84
 11  \w     81.00 178.00   1.00    1.50    --  109.13  30.00-180.00   97
 12  \w     94.00 178.00   1.00    1.50    --  109.13 125.00 150.00   84
 13  \w   -114.00 -14.00   1.00    1.00    --  -41.80 -57.00 -30.00  100
 14  \w     48.00 118.00   1.00    1.00    --   41.80  77.00 -60.00   70
 15  \w      9.00 118.00   1.00    1.00    --   41.80  77.00 120.00  109
 16  \w     36.00 121.00   1.00    1.50    --  109.13-125.00 120.00   85
 17  \w     83.00 178.00   1.00    1.50    --  109.13  45.00  30.00   95
 18  \w     80.00 178.00   1.00    1.50    --  109.13  61.00-150.00   98
 19  \w     80.00 178.00   1.00    1.50    --  109.13  61.00 -90.00   98
 20  \w     80.00 178.00   1.00    1.50    --  109.13  61.00  60.00   98
 21  \w     77.00 178.00   1.00    1.50    --  109.13  77.00  90.00  101
 22  \w    -70.00  31.00   1.00    1.00    --  -41.80  57.00  30.00  101
 23  \w      9.00 118.00   1.00    1.00    --   41.80  77.00 -90.00  109
 24  \w     14.00 115.00   1.00    1.00    --   41.80  57.00  60.00  101
 25  \w     77.00 178.00   1.00    1.50    --  109.13  77.00 -30.00  101
;
_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      -0.0531837000
_diffrn_orient_matrix_UB_12      0.0424142000
_diffrn_orient_matrix_UB_13      -0.1269483000
_diffrn_orient_matrix_UB_21      -0.1672057000
_diffrn_orient_matrix_UB_22      -0.0064560000
_diffrn_orient_matrix_UB_23      -0.0149881000
_diffrn_orient_matrix_UB_31      0.0257607000
_diffrn_orient_matrix_UB_32      0.0457725000
_diffrn_orient_matrix_UB_33      0.1156362000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13153
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.439
_diffrn_reflns_theta_min         3.600
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.929
_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             840
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(17)
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4052
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0536P)^2^+0.7659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                3780
_reflns_number_total             4052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00953_si_006.cif
_cod_data_source_block           evde_ugent011
_cod_database_code               4035570
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C24 H28 N2 O3'
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.88 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              86014
_shelx_hkl_checksum              71231
_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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.733