Cationic Gold(I)-Catalyzed Cascade Bicyclizations for Divergent Synthesis of (Spiro)polyheterocycles
Li, Zhenghua; Song, Liangliang; Van Meervelt, Luc; Tian, Guilong; Van der Eycken, Erik V.; ACS Catalysis 8 (2018) 6388–; doi:10.1021/acscatal.8b01789

data_4515677
_publ_section_title
;
 Cationic Gold(I)-Catalyzed Cascade Bicyclizations for Divergent Synthesis
 of (Spiro)polyheterocycles
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6388
_journal_paper_doi               10.1021/acscatal.8b01789
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C31 H38 N2 O3, C2 H3 N'
_chemical_formula_sum            'C33 H41 N3 O3'
_chemical_formula_weight         527.69
_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   geom
_audit_creation_date             2016-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                107.862(3)
_cell_angle_beta                 96.620(2)
_cell_angle_gamma                114.133(3)
_cell_formula_units_Z            2
_cell_length_a                   11.5304(3)
_cell_length_b                   11.8994(3)
_cell_length_c                   12.6132(4)
_cell_measurement_reflns_used    1596
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.6830
_cell_measurement_theta_min      3.5180
_cell_volume                     1444.35(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(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -20.00  25.00   1.00   30.00    --  -16.84 -99.00 -30.00   45
  2  \w    -20.00  25.00   1.00   30.00    --  -16.84 -99.00 150.00   45
  3  \w     34.00  95.00   1.00   30.00    --   18.87-178.00  60.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, single source at offset, Eos detector'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0195029000
_diffrn_orient_matrix_UB_12      0.0225810000
_diffrn_orient_matrix_UB_13      0.0502558000
_diffrn_orient_matrix_UB_21      0.0656428000
_diffrn_orient_matrix_UB_22      0.0519263000
_diffrn_orient_matrix_UB_23      0.0285419000
_diffrn_orient_matrix_UB_31      -0.0147877000
_diffrn_orient_matrix_UB_32      0.0427901000
_diffrn_orient_matrix_UB_33      -0.0211923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26238
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.575
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0525P)^2^+1.2680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4924
_reflns_number_total             5892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01789_si_002.cif
_cod_data_source_block           ev2006
_cod_original_cell_volume        1444.35(8)
_cod_database_code               4515677
_chemical_oxdiff_formula         'C31 H32 N2 O3'
_chemical_oxdiff_usercomment     ZL-1441D
_reflns_odcompleteness_completeness 52.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C19(H19), C20(H20), C22(H22),
 C23(H23), N28(H28)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,
 H37B,H37C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-24
_olex2_submission_original_sample_id ZL-1441
_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 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.889