#------------------------------------------------------------------------------
#$Date: 2025-10-06 13:25:22 +0300 (Mon, 06 Oct 2025) $
#$Revision: 302751 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/06/7160649.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160649
loop_
_publ_author_name
'Gou, Yan'
'Hou, Shanling'
'Fu, Qingyi'
'Fan, Zhi'
'Li, Yuming'
_publ_section_title
;
 Diastereoselective synthesis of
 spiro[cyclopropane-1,3'-indolin]-2'-imines via a sequential [1 +
 2] annulation reaction of indolin-2-imines with α-aryl
 vinylsulfonium salts.
;
_journal_issue                   32
_journal_name_full               'Organic & 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       'ω and φ 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 λ/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/[σ²(Fo²)+(0.0679P)²+1.9980P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.47683(17) 0.50262(15) 0.22657(7) 0.0427(3) Uani 1 1 d . . . . .
Cl1 Cl 0.2871(2) 0.16424(19) 0.45920(9) 0.0699(5) Uani 1 1 d . . . . .
O2 O 0.5129(5) 0.5198(5) 0.2967(2) 0.0592(10) Uani 1 1 d . . . . .
O1 O 0.3706(5) 0.6297(4) 0.1936(2) 0.0642(11) Uani 1 1 d . . . . .
N2 N 0.2106(5) 0.1146(4) 0.2372(2) 0.0402(9) Uani 1 1 d . . . . .
N1 N 0.3986(5) 0.3318(5) 0.2228(2) 0.0419(10) Uani 1 1 d . . . . .
C8 C 0.2392(6) 0.2626(5) 0.2524(2) 0.0378(10) Uani 1 1 d . . . . .
C9 C 0.0664(6) 0.3091(5) 0.3010(2) 0.0343(10) Uani 1 1 d . . . . .
C10 C -0.0658(6) 0.1721(5) 0.3083(2) 0.0369(10) Uani 1 1 d . . . . .
C17 C 0.0870(6) 0.4009(5) 0.3638(2) 0.0381(11) Uani 1 1 d . . . . .
H17 H 0.2186 0.4380 0.3629 0.046 Uiso 1 1 calc R . . . .
C11 C 0.0292(6) 0.0586(5) 0.2692(3) 0.0391(11) Uani 1 1 d . . . . .
C16 C -0.0036(7) 0.4786(5) 0.3038(3) 0.0408(11) Uani 1 1 d . . . . .
H16A H 0.0681 0.5636 0.2698 0.049 Uiso 1 1 calc R . . . .
H16B H -0.1425 0.4968 0.3135 0.049 Uiso 1 1 calc R . . . .
C18 C -0.0202(6) 0.3489(5) 0.4365(2) 0.0376(10) Uani 1 1 d . . . . .
C12 C -0.0543(8) -0.0823(6) 0.2622(3) 0.0495(13) Uani 1 1 d . . . . .
H12 H 0.0117 -0.1584 0.2347 0.059 Uiso 1 1 calc R . . . .
C5 C 0.7006(7) 0.4944(6) 0.1704(3) 0.0424(11) Uani 1 1 d . . . . .
C15 C -0.2484(7) 0.1474(6) 0.3418(3) 0.0437(12) Uani 1 1 d . . . . .
H15 H -0.3151 0.2252 0.3681 0.052 Uiso 1 1 calc R . . . .
C19 C 0.0602(7) 0.2402(6) 0.4849(3) 0.0436(12) Uani 1 1 d . . . . .
C23 C -0.1991(7) 0.4099(7) 0.4609(3) 0.0523(13) Uani 1 1 d . . . . .
H23 H -0.2589 0.4846 0.4299 0.063 Uiso 1 1 calc R . . . .
C20 C -0.0313(8) 0.1924(7) 0.5538(3) 0.0547(14) Uani 1 1 d . . . . .
H20 H 0.0271 0.1171 0.5851 0.066 Uiso 1 1 calc R . . . .
C14 C -0.3352(7) 0.0063(6) 0.3366(3) 0.0540(14) Uani 1 1 d . . . . .
H14 H -0.4621 -0.0130 0.3604 0.065 Uiso 1 1 calc R . . . .
C6 C 0.7892(7) 0.3527(7) 0.1567(3) 0.0539(14) Uani 1 1 d . . . . .
H6 H 0.7272 0.2545 0.1754 0.065 Uiso 1 1 calc R . . . .
C13 C -0.2402(8) -0.1060(6) 0.2977(3) 0.0549(14) Uani 1 1 d . . . . .
H13 H -0.3029 -0.2016 0.2951 0.066 Uiso 1 1 calc R . . . .
C4 C 0.7928(8) 0.6368(7) 0.1439(3) 0.0561(14) Uani 1 1 d . . . . .
H4 H 0.7328 0.7353 0.1533 0.067 Uiso 1 1 calc R . . . .
C24 C 0.3476(8) 0.0274(6) 0.1917(3) 0.0610(16) Uani 1 1 d . . . . .
H24A H 0.3071 0.0284 0.1454 0.091 Uiso 1 1 calc GR . . . .
H24B H 0.3564 -0.0831 0.2146 0.091 Uiso 1 1 calc GR . . . .
H24C H 0.4720 0.0778 0.1845 0.091 Uiso 1 1 calc GR . . . .
C21 C -0.2061(8) 0.2539(7) 0.5766(3) 0.0575(15) Uani 1 1 d . . . . .
H21 H -0.2698 0.2224 0.6242 0.069 Uiso 1 1 calc R . . . .
C22 C -0.2903(7) 0.3619(7) 0.5305(3) 0.0593(15) Uani 1 1 d . . . . .
H22 H -0.4125 0.4041 0.5466 0.071 Uiso 1 1 calc R . . . .
C2 C 1.0634(8) 0.4964(9) 0.0893(3) 0.0615(16) Uani 1 1 d . . . . .
C7 C 0.9692(8) 0.3529(8) 0.1157(3) 0.0626(16) Uani 1 1 d . . . . .
H7 H 1.0289 0.2548 0.1056 0.075 Uiso 1 1 calc R . . . .
C3 C 0.9711(8) 0.6346(8) 0.1043(3) 0.0685(17) Uani 1 1 d . . . . .
H3 H 1.0331 0.7331 0.0864 0.082 Uiso 1 1 calc R . . . .
C1 C 1.2606(9) 0.4947(10) 0.0444(4) 0.090(2) Uani 1 1 d . . . . .
H1A H 1.3558 0.5018 0.0749 0.135 Uiso 1 1 calc GR . . . .
H1B H 1.2734 0.5859 0.0063 0.135 Uiso 1 1 calc GR . . . .
H1C H 1.2799 0.3953 0.0232 0.135 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 112.6(2) . . ?
O2 S1 C5 106.9(2) . . ?
O1 S1 O2 115.9(3) . . ?
O1 S1 N1 112.7(2) . . ?
O1 S1 C5 107.0(2) . . ?
N1 S1 C5 100.1(2) . . ?
C8 N2 C11 111.5(4) . . ?
C8 N2 C24 124.3(4) . . ?
C11 N2 C24 124.2(4) . . ?
C8 N1 S1 131.4(4) . . ?
N2 C8 C9 107.6(4) . . ?
N1 C8 N2 117.6(4) . . ?
N1 C8 C9 134.8(4) . . ?
C8 C9 C10 104.3(4) . . ?
C8 C9 C17 119.6(4) . . ?
C8 C9 C16 124.2(4) . . ?
C10 C9 C17 123.5(4) . . ?
C10 C9 C16 122.4(4) . . ?
C16 C9 C17 57.9(3) . . ?
C11 C10 C9 107.2(4) . . ?
C15 C10 C9 132.6(4) . . ?
C15 C10 C11 120.1(4) . . ?
C16 C17 C9 59.7(3) . . ?
C16 C17 C18 123.2(4) . . ?
C18 C17 C9 120.0(4) . . ?
C10 C11 N2 109.3(4) . . ?
C12 C11 N2 128.0(4) . . ?
C12 C11 C10 122.6(4) . . ?
C17 C16 C9 62.4(3) . . ?
C19 C18 C17 120.4(4) . . ?
C23 C18 C17 122.5(4) . . ?
C23 C18 C19 117.0(5) . . ?
C11 C12 C13 116.3(5) . . ?
C6 C5 S1 122.4(4) . . ?
C6 C5 C4 119.7(5) . . ?
C4 C5 S1 117.7(4) . . ?
C10 C15 C14 118.6(5) . . ?
C18 C19 Cl1 119.7(4) . . ?
C20 C19 Cl1 117.8(4) . . ?
C20 C19 C18 122.5(5) . . ?
C22 C23 C18 120.2(5) . . ?
C21 C20 C19 119.5(5) . . ?
C13 C14 C15 121.0(5) . . ?
C5 C6 C7 120.0(5) . . ?
C14 C13 C12 121.3(5) . . ?
C3 C4 C5 119.4(6) . . ?
C20 C21 C22 119.8(5) . . ?
C21 C22 C23 121.0(5) . . ?
C7 C2 C1 119.9(6) . . ?
C3 C2 C7 117.7(5) . . ?
C3 C2 C1 122.4(6) . . ?
C6 C7 C2 120.5(6) . . ?
C2 C3 C4 122.6(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.438(4) . ?
S1 O1 1.433(4) . ?
S1 N1 1.584(4) . ?
S1 C5 1.771(5) . ?
Cl1 C19 1.741(5) . ?
N2 C8 1.355(6) . ?
N2 C11 1.402(6) . ?
N2 C24 1.448(6) . ?
N1 C8 1.301(6) . ?
C8 C9 1.488(6) . ?
C9 C10 1.498(6) . ?
C9 C17 1.549(6) . ?
C9 C16 1.509(6) . ?
C10 C11 1.386(6) . ?
C10 C15 1.361(6) . ?
C17 C16 1.481(6) . ?
C17 C18 1.482(6) . ?
C11 C12 1.386(7) . ?
C18 C19 1.396(7) . ?
C18 C23 1.391(6) . ?
C12 C13 1.391(7) . ?
C5 C6 1.373(7) . ?
C5 C4 1.383(7) . ?
C15 C14 1.388(7) . ?
C19 C20 1.378(7) . ?
C23 C22 1.388(7) . ?
C20 C21 1.362(8) . ?
C14 C13 1.377(8) . ?
C6 C7 1.386(7) . ?
C4 C3 1.366(8) . ?
C21 C22 1.379(8) . ?
C2 C7 1.396(8) . ?
C2 C3 1.364(9) . ?
C2 C1 1.519(8) . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.036 0.000 0.000 139 45 ' '
