Gold(I)-Catalyzed Pathway-Switchable Tandem Cycloisomerizations to Indolizino[8,7-b]indole and Indolo[2,3-a]quinolizine Derivatives
Liu, Chengjun; Sun, Zenghui; Xie, Fukai; Liang, Guoduan; Yang, Lu; Li, Yaqiao; Cheng, Mao-sheng; Lin, Bin; Liu, Yongxiang; Chemical Communications  (2019) –; doi:10.1039/C9CC05667J

data_7124345
_publ_section_title
;
 Gold(I)-Catalyzed Pathway-Switchable Tandem Cycloisomerizations to
 Indolizino[8,7-b]indole and Indolo[2,3-a]quinolizine Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05667J
_journal_year                    2019
_chemical_formula_moiety         'C38 H36 N2 O Si'
_chemical_formula_sum            'C38 H36 N2 O Si'
_chemical_formula_weight         564.78
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2019-04-17 deposited with the CCDC.    2019-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                88.276(3)
_cell_angle_beta                 83.244(4)
_cell_angle_gamma                77.357(4)
_cell_formula_units_Z            4
_cell_length_a                   10.0141(5)
_cell_length_b                   16.8417(6)
_cell_length_c                   18.3913(8)
_cell_measurement_reflns_used    7751
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4590
_cell_measurement_theta_min      2.3870
_cell_volume                     3005.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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      8.00  80.00   1.00    1.00    --   40.98 -99.00   0.00   72
  2  \w     35.00  68.00   1.00    1.00    --   40.98-125.00 -60.00   33
  3  \w     44.00  82.00   1.00    1.00    --   40.98-125.00-180.00   38
  4  \w     35.00 136.00   1.00    1.00    --  106.95 -61.00-150.00  101
  5  \w     88.00 117.00   1.00    1.00    --  106.95-125.00 -60.00   29
  6  \w     48.00  93.00   1.00    1.00    --  106.95 -94.00  60.00   45
  7  \w     48.00  99.00   1.00    1.00    --  106.95 -94.00 120.00   51
  8  \w     32.00 105.00   1.00    1.00    --  106.95 -30.00  30.00   73
  9  \w     67.00 178.00   1.00    1.00    --  106.95  15.00 -30.00  111
 10  \w    138.00 165.00   1.00    1.00    --  106.95  77.00   0.00   27
 11  \w    129.00 178.00   1.00    1.00    --  106.95 125.00  60.00   49
 12  \w    109.00 177.00   1.00    1.00    --  106.95 125.00 120.00   68
 13  \w     86.00 113.00   1.00    1.00    --  106.95  77.00   0.00   27
 14  \w     82.00 147.00   1.00    1.00    --  106.95  45.00-120.00   65
 15  \w     75.00 176.00   1.00    1.00    --  106.95  77.00-180.00  101
 16  \w     24.00 104.00   1.00    1.00    --  106.95 -94.00-180.00   80
 17  \w    -81.00  39.00   1.00    1.00    --  -40.98  19.00-120.00  120
 18  \w   -100.00 -64.00   1.00    1.00    --  -40.98-160.00 170.00   36
 19  \w   -110.00 -35.00   1.00    1.00    --  -40.98 -38.00  60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0031243000
_diffrn_orient_matrix_UB_12      0.0109652000
_diffrn_orient_matrix_UB_13      0.0830873000
_diffrn_orient_matrix_UB_21      0.0440162000
_diffrn_orient_matrix_UB_22      -0.0929180000
_diffrn_orient_matrix_UB_23      0.0094866000
_diffrn_orient_matrix_UB_31      0.1524359000
_diffrn_orient_matrix_UB_32      0.0058817000
_diffrn_orient_matrix_UB_33      -0.0110355000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21813
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.628
_diffrn_reflns_theta_min         2.419
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     763
_refine_ls_number_reflns         11721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0937P)^2^+1.8189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.1928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9300
_reflns_number_total             11721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05667j2.cif
_cod_data_source_block           exp_1493
_cod_database_code               7124345
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.97
_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.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C01F(H01A,H01B), C11(H11A,H11B), C10(H10A,H10B), C024(H02D,
 H02E), C026(H02I,H02J)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C15(H15), C2(H2), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U),
 C21(H21), C14(H14), C22(H22), C011(H011), C25(H25), C30(H30), C016(H016),
 C017(H017), C24(H24), C019(H019), C23(H23), C01C(H01C), C01D(H01D), C3(H3),
 C01H(H01H), C5(H5), C01K(H01K), C01L(H01L), C01M(H01M), C38(H38), C27(H27),
 C01Q(H01Q), C01R(H01R), C01V(H01V), C01W(H01W), C4(H4), C01Z(H01Z), C29(H29),
 C021(H021), C28(H28), C028(H028), C37(H37), C36(H36), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C01X(H01E,H01F,H01G), C023(H02A,
 H02B,H02C), C025(H02F,H02G,H02H), C17(H17A,H17B,H17C)
;