Diastereoselective reaction to construct polycyclic spiroindolines from 3-(2-isocyanoethyl)indoles and ynones
Liang, Demin; Wu, Da; Shen, Jie; Lu, Shanya; Wang, Jiale; Yan, Xiaodong; Li, Jian; New Journal of Chemistry 49 (2025) 11371–11375; doi:10.1039/D5NJ01268F

data_7063837
_publ_section_title
;
 Diastereoselective reaction to construct polycyclic spiroindolines from
 3-(2-isocyanoethyl)indoles and ynones
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11371
_journal_page_last               11375
_journal_paper_doi               10.1039/D5NJ01268F
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C26 H18 Br Cl N2 O'
_chemical_formula_sum            'C26 H18 Br Cl N2 O'
_chemical_formula_weight         489.78
_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
_audit_creation_date             2023-10-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-07 deposited with the CCDC.	2025-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.660(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0752(5)
_cell_length_b                   19.2241(11)
_cell_length_c                   12.5601(7)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      4.60
_cell_volume                     2099.3(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16176
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.762
_diffrn_reflns_theta_max         66.762
_diffrn_reflns_theta_min         4.600
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.009
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5666
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.7527.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.485
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0399P)^2^+3.1326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3620
_reflns_number_total             3697
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj01268f2.cif
_cod_data_source_block           cu_20210416d_0m_a
_cod_depositor_comments          'Adding full bibliography for 7063837.cif.'
_cod_database_code               7063837
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.645
_shelx_estimated_absorpt_t_min   0.532
_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:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              99167
_olex2_submission_special_instructions 'No special instructions were received'