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_1554327
_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         'C26 H21 F2 N3'
_chemical_formula_sum            'C26 H21 F2 N3'
_chemical_formula_weight         413.46
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-25
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.76710(10)
_cell_length_b                   18.76710(10)
_cell_length_c                   24.2076(3)
_cell_measurement_reflns_used    20897
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0100
_cell_measurement_theta_min      4.6630
_cell_volume                     8526.01(12)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -30.00  11.00   1.00    3.00    --    0.00  82.00  60.00   41
  2  \w    -82.00 -57.00   1.00    3.00    --    0.00 -57.00 -30.00   25
  3  \w    -18.00   8.00   1.00    3.00    --    0.00 -57.00 -30.00   26
  4  \w    -18.00  26.00   1.00    3.00    --    0.00  38.00-180.00   44
  5  \w     29.00  88.00   1.00    3.00    --    0.00  38.00-180.00   59
  6  \w    -21.00  16.00   1.00    3.00    --    0.00  57.00  60.00   37
  7  \w     19.00  89.00   1.00    3.00    --    0.00  82.00  60.00   70
  8  \w    -38.00   8.00   1.00    3.00    --    0.00 -38.00-150.00   46
  9  \w    -86.00 -49.00   1.00    3.00    --    0.00 -38.00-150.00   37
 10  \w     79.00 105.00   1.00    7.00    --   95.80  45.00 -90.00   26
 11  \w     89.00 115.00   1.00    7.00    --   95.80 -82.00 -30.00   26
 12  \w     65.00 115.00   1.00    7.00    --   95.80 -30.00  30.00   50
 13  \w     58.00 116.00   1.00    7.00    --   95.80 -45.00-150.00   58
 14  \w     60.00  88.00   1.00    7.00    --   95.80 -82.00 150.00   28
 15  \w      8.00 127.00   1.00    7.00    --   95.80 -82.00 -60.00  119
 16  \w     12.00  42.00   1.00    7.00    --   95.80 -61.00 -60.00   30
 17  \w     89.00 127.00   1.00    7.00    --   95.80 -82.00  90.00   38
 18  \w     53.00  79.00   1.00    7.00    --   95.80 -82.00-150.00   26
 19  \w     47.00 127.00   1.00    7.00    --   95.80 -82.00  30.00   80
 20  \w     49.00  75.00   1.00    7.00    --   95.80 -82.00  90.00   26
 21  \w     86.00 121.00   1.00    7.00    --   95.80 -82.00-150.00   35
 22  \w     10.00  36.00   1.00    7.00    --   95.80 -30.00  30.00   26
 23  \w     15.00  85.00   1.00    7.00    --   95.80 -45.00  60.00   70
 24  \w    142.00 171.00   1.00    7.00    --   95.80  15.00  30.00   29
 25  \w     68.00 137.00   1.00    7.00    --   95.80  15.00  30.00   69
 26  \w      6.00 122.00   1.00    7.00    --   95.80 -15.00 120.00  116
 27  \w     96.00 125.00   1.00    7.00    --   95.80 -82.00 150.00   29
 28  \w     55.00 115.00   1.00    7.00    --   95.80 -61.00 -60.00   60
 29  \w     33.00  97.00   1.00    7.00    --   95.80 -82.00-180.00   64
 30  \w     92.00 118.00   1.00    7.00    --   95.80 -82.00  60.00   26
 31  \w     32.00 115.00   1.00    7.00    --   95.80 -15.00 -30.00   83
;
_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      -0.0598176000
_diffrn_orient_matrix_UB_12      -0.0555947000
_diffrn_orient_matrix_UB_13      0.0065172000
_diffrn_orient_matrix_UB_21      0.0511940000
_diffrn_orient_matrix_UB_22      -0.0589788000
_diffrn_orient_matrix_UB_23      -0.0195319000
_diffrn_orient_matrix_UB_31      0.0231104000
_diffrn_orient_matrix_UB_32      -0.0131494000
_diffrn_orient_matrix_UB_33      0.0602256000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44385
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.058
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         4.713
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36817
_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    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0420P)^2^+8.3800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3491
_reflns_number_total             3816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00382c2.cif
_cod_data_source_block           exp_229
_cod_original_cell_volume        8526.01(14)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               1554327
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.95
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              35298
_shelx_hkl_checksum              55213
_shelx_fab_checksum              39645
_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 6.636
_oxdiff_exptl_absorpt_empirical_full_min 0.186