Stereoselective synthesis of 3-spiropiperidino indolenines via S<sub>N</sub>2-type ring opening of activated aziridines with 1H-indoles/Pd-catalyzed spirocyclization with propargyl carbonates.
Pradhan, Sajan; Shahi, Chandan Kumar; Bhattacharyya, Aditya; Ghorai, Manas K.; Chemical communications (Cambridge, England) 54 (2018) 8583–8586; doi:10.1039/c8cc04249g

data_7121848
_publ_section_title
;
 Stereoselective synthesis of 3-spiropiperidino indolenines via
 S<sub>N</sub>2-type ring opening of activated aziridines with
 1H-indoles/Pd-catalyzed spirocyclization with propargyl carbonates.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8583
_journal_page_last               8586
_journal_paper_doi               10.1039/c8cc04249g
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C33 H30 N2 O2 S'
_chemical_formula_sum            'C33 H30 N2 O2 S'
_chemical_formula_weight         518.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-24 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.461(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7368(6)
_cell_length_b                   16.8658(12)
_cell_length_c                   20.2866(14)
_cell_measurement_reflns_used    4548
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      2.42
_cell_volume                     2630.3(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1806
_diffrn_reflns_av_unetI/netI     0.1753
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            39664
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.423
_diffrn_reflns_theta_min         2.618
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6261
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.8396.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1936
_refine_ls_R_factor_gt           0.0804
_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^)+(0.0825P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3291
_reflns_number_total             6599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04249g2.cif
_cod_data_source_block           sp
_cod_depositor_comments          'Adding full bibliography for 7121848.cif.'
_cod_database_code               7121848
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.997
_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:
 C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00A(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00E), C00K(H00K), C00O(H00O), C00X(H00X), C00P(H00P), C00L(H00L),
 C00Q(H00Q), C00R(H00R), C00U(H00U), C00M(H00M), C009(H009), C00T(H00T),
 C010(H010), C011(H011), C00W(H00W), C00S(H00S), C00Z(H00Z)
2.d Fitted hexagon refined as free rotating group:
 C00K(C00B,C00O,C00X,C00P,C00L), C00R(C00V,C00U,C00M,C00G,C009), C010(C011,
 C00W,C00N,C00S,C00Z)
2.e X=CH2 refined with riding coordinates:
 C00H(H00G,H00H)
2.f Idealised Me refined as rotating group:
 C00Y(H00I,H00J,H00N), C012(H01A,H01B,H01C)
;
_olex2_submission_special_instructions 'No special instructions were received'