A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with indole-derived ketimines: rapid access to hexacyclic spiroindolines
Liu, Yun-Lin; Mao, Xiang-Yu; Lin, Xiao-Tong; Chen, Guo-Shu; Organic Chemistry Frontiers 5 (2018) 2303–; doi:10.1039/C8QO00382C

data_1554325
_publ_section_title
;
 A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with
 indole-derived ketimines: rapid access to hexacyclic spiroindolines
;
_journal_issue                   15
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2303
_journal_paper_doi               10.1039/C8QO00382C
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C25 H19 N3 O'
_chemical_formula_sum            'C25 H19 N3 O'
_chemical_formula_weight         377.43
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-15 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                101.330(2)
_cell_angle_beta                 95.203(2)
_cell_angle_gamma                106.126(2)
_cell_formula_units_Z            4
_cell_length_a                   8.2339(2)
_cell_length_b                   14.7918(4)
_cell_length_c                   17.1794(5)
_cell_measurement_reflns_used    11984
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1900
_cell_measurement_theta_min      4.6090
_cell_volume                     1947.28(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_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     49.00  89.00   1.00    1.00    --    0.00  57.00  30.00   40
  2  \w     33.00  88.00   1.00    1.00    --    0.00  38.00-150.00   55
  3  \w     10.00  83.00   1.00    1.00    --    0.00  77.00-120.00   73
  4  \w    -23.00  32.00   1.00    1.00    --    0.00  57.00  30.00   55
  5  \w    -89.00 -14.00   1.00    1.00    --    0.00 -77.00-180.00   75
  6  \w      6.00  59.00   1.00    1.00    --   95.80 -82.00-150.00   53
  7  \w     72.00 182.00   1.00    1.00    --   95.80  15.00 -60.00  110
  8  \w     10.00 127.00   1.00    1.00    --   95.80 -82.00  90.00  117
  9  \w     38.00  63.00   1.00    1.00    --   95.80 -82.00 150.00   25
 10  \w     53.00  79.00   1.00    1.00    --   95.80 -61.00  30.00   26
 11  \w     56.00 127.00   1.00    1.00    --   95.80 -82.00 -30.00   71
 12  \w      7.00 101.00   1.00    1.00    --   95.80 -30.00  90.00   94
 13  \w     47.00 103.00   1.00    1.00    --   95.80 -61.00 -30.00   56
 14  \w      8.00  41.00   1.00    1.00    --   95.80 -61.00  30.00   33
 15  \w     48.00 120.00   1.00    1.00    --   95.80 -61.00-150.00   72
 16  \w      9.00  42.00   1.00    1.00    --   95.80 -61.00-150.00   33
 17  \w      7.00  53.00   1.00    1.00    --   95.80 -15.00 -60.00   46
 18  \w     58.00 122.00   1.00    1.00    --   95.80 -15.00 -60.00   64
 19  \w     93.00 127.00   1.00    1.00    --   95.80 -82.00  30.00   34
 20  \w     67.00 122.00   1.00    1.00    --   95.80 -82.00-150.00   55
 21  \w     48.00 102.00   1.00    1.00    --   95.80 -30.00-180.00   54
 22  \w     94.00 119.00   1.00    1.00    --   95.80 -82.00 150.00   25
 23  \w     94.00 120.00   1.00    1.00    --   95.80 -82.00  60.00   26
 24  \w     85.00 110.00   1.00    1.00    --   95.80 -82.00 120.00   25
 25  \w     34.00 108.00   1.00    1.00    --   95.80 -30.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0761891000
_diffrn_orient_matrix_UB_12      -0.1106795000
_diffrn_orient_matrix_UB_13      -0.0287547000
_diffrn_orient_matrix_UB_21      0.0419539000
_diffrn_orient_matrix_UB_22      -0.0106629000
_diffrn_orient_matrix_UB_23      0.0863356000
_diffrn_orient_matrix_UB_31      -0.1768944000
_diffrn_orient_matrix_UB_32      0.0075501000
_diffrn_orient_matrix_UB_33      0.0169552000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19522
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.608
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         6920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0350P)^2^+1.0360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6266
_reflns_number_total             6920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00382c2.cif
_cod_data_source_block           exp_234
_cod_depositor_comments
;

2022-04-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1947.28(9)
_cod_original_formula_moiety     '2(C25 H19 N3 O)'
_cod_original_formula_sum        'C50 H38 N6 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     754.86
_cod_database_code               1554325
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.813
_shelx_estimated_absorpt_t_min   0.764
_reflns_odcompleteness_completeness 99.71
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C34(H34A,H34B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31), C40(H40), C41(H41), C42(H42), C43(H43), C46(H46),
 C47(H47), C48(H48), C49(H49), C50(H50)
;
_shelx_res_checksum              11961
_shelx_hkl_checksum              10516
_shelx_fab_checksum              84486
_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 2.524
_oxdiff_exptl_absorpt_empirical_full_min 0.486