Diastereoselective synthesis of spiro[cyclopropane-1,3'-indolin]-2'-imines <i>via</i> a sequential [1 + 2] annulation reaction of indolin-2-imines with α-aryl vinylsulfonium salts.
Gou, Yan; Hou, Shanling; Fu, Qingyi; Fan, Zhi; Li, Yuming; Organic & biomolecular chemistry 23 (2025) 7415–7419; doi:10.1039/d5ob01012h

data_7160649
_publ_section_title
;
 Diastereoselective synthesis of
 spiro[cyclopropane-1,3'-indolin]-2'-imines <i>via</i> a sequential [1 +
 2] annulation reaction of indolin-2-imines with &#x3b1;-aryl
 vinylsulfonium salts.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7415
_journal_page_last               7419
_journal_paper_doi               10.1039/d5ob01012h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C24 H21 Cl N2 O2 S'
_chemical_formula_sum            'C24 H22 Cl N2 O2 S'
_chemical_formula_weight         437.94
_chemical_name_systematic        organic
_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   geom
_audit_creation_date             2025-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2025-06-06 deposited with the CCDC.	2025-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                81.94(2)
_cell_angle_beta                 79.89(2)
_cell_angle_gamma                88.02(2)
_cell_formula_units_Z            2
_cell_length_a                   7.158(5)
_cell_length_b                   8.464(7)
_cell_length_c                   19.143(15)
_cell_measurement_reflns_used    2125
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.978
_cell_measurement_theta_min      2.182
_cell_volume                     1130.4(15)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8696
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.182
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1208 before and 0.0605 after correction. The Ratio of minimum to maximum transmission is 0.6828. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             458
_exptl_crystal_preparation       organic
_exptl_crystal_recrystallization_method organic
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0868
_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^)+(0.0679P)^2^+1.9980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2763
_reflns_number_total             5032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01012h2.cif
_cod_data_source_block           nts-y2cl
_cod_depositor_comments          'Adding full bibliography for 7160649.cif.'
_cod_database_code               7160649
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C23(H23), C20(H20), C14(H14), C6(H6), C13(H13), C4(H4),
 C21(H21), C22(H22), C7(H7), C3(H3)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              66551
_shelx_fab_checksum              38456
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'