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_1554326
_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 H16 F3 N3 O2'
_chemical_formula_sum            'C25 H16 F3 N3 O2'
_chemical_formula_weight         447.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2018-03-17 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.178(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.5242(3)
_cell_length_b                   8.44750(10)
_cell_length_c                   25.5820(4)
_cell_measurement_reflns_used    19854
_cell_measurement_temperature    100(10)
_cell_measurement_theta_max      74.2440
_cell_measurement_theta_min      5.5160
_cell_volume                     4031.04(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            43726
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.361
_diffrn_reflns_theta_min         3.692
_exptl_absorpt_coefficient_mu    0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_transmission_factor_max   0.824
_exptl_transmission_factor_min   0.785
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         8129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7388
_reflns_number_total             8222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00382c2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554326
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C18(H18A,H18B), C44(H44A,H44B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C39(H39), C35(H35), C28(H28), C50(H50), C10(H10), C3(H3), C27(H27), C5(H5),
 C25(H25), C24(H24), C14(H14), C47(H47), C23(H23), C22(H22), C4(H4), C29(H29),
 C2(H2), C38(H38), C11(H11), C30(H30), C13(H13), C49(H49), C36(H36), C48(H48)
;
_shelx_res_checksum              42628
_shelx_hkl_checksum              48856
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'