Synthesis of polycyclic spiroindolines <i>via</i> the cascade reaction of 3-(2-isocyanoethyl)indoles.
Li, Haizhen; Wu, Jinyu; Zheng, Jianfeng; Li, Wei-Dong Z; Chemical communications (Cambridge, England) 57 (2021) 11092–11095; doi:10.1039/d1cc04576h

data_7129049
_publ_section_title
;
 Synthesis of polycyclic spiroindolines <i>via</i> the cascade reaction of
 3-(2-isocyanoethyl)indoles.
;
_journal_issue                   84
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11092
_journal_page_last               11095
_journal_paper_doi               10.1039/d1cc04576h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C29 H31 N3 O6'
_chemical_formula_sum            'C29 H31 N3 O6'
_chemical_formula_weight         517.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-17 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.329(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8169(18)
_cell_length_b                   16.0922(13)
_cell_length_c                   23.146(2)
_cell_measurement_reflns_used    2666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2980
_cell_measurement_theta_min      3.3320
_cell_volume                     5681.7(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   21.20   0.7000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000 -120.0000 66

  2 omega  -52.00   33.40   0.7000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086  -38.0000   90.0000 122

  3 omega  -12.00   88.10   0.7000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   19.0000   90.0000 143
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0444282000
_diffrn_orient_matrix_UB_12      -0.0039733000
_diffrn_orient_matrix_UB_13      -0.0005497000
_diffrn_orient_matrix_UB_21      0.0134660000
_diffrn_orient_matrix_UB_22      0.0057305000
_diffrn_orient_matrix_UB_23      0.0315051000
_diffrn_orient_matrix_UB_31      -0.0022501000
_diffrn_orient_matrix_UB_32      -0.0435164000
_diffrn_orient_matrix_UB_33      0.0042054000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13458
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.016
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5791
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0884P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3381
_reflns_number_total             5791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04576h2.cif
_cod_data_source_block           210818_s1_lgg
_cod_depositor_comments
'Adding full bibliography for 7129048--7129049.cif.'
_cod_original_cell_volume        5681.8(10)
_cod_database_code               7129049
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 99.73
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C28-O6 = C28-C29 = C28-C29A = C25-C26A
 1.55 with sigma of 0.02
 H29B-H29F
 1.37 with sigma of 0.02
 H29C-H29E
 1.2 with sigma of 0.02
 H26A-H26D
 1.64 with sigma of 0.02
 H25B-H26F
 1.38 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C29A)
Uanis(C26) = Uanis(C26A)
Uanis(C26A) = Uanis(C26) = Uanis(C29A) = Uanis(C29)
4. Others
 Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
 Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(2)
 Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C25(H25A,H25B), C25(H25C,H25D), C28(H28A,H28B),
 C28(H28C,H28D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C26(H26A,H26B,H26C), C29(H29A,H29B,
 H29C), C29A(H29D,H29E,H29F), C26A(H26D,H26E,H26F)
;
_shelx_res_checksum              9017
_olex2_submission_special_instructions 'No special instructions were received'