Nucleophilic Ring Opening of Donor-Acceptor Cyclopropanes with the Cyanate Ion: Access to Spiro[pyrrolidone-3,3'-oxindoles].
Zaytsev, Sergey V.; Ivanov, Konstantin L.; Skvortsov, Dmitry A.; Bezzubov, Stanislav I.; Melnikov, Mikhail Ya; Budynina, Ekaterina M.; The Journal of organic chemistry 83 (2018) 8695–8709; doi:10.1021/acs.joc.8b00922

data_4035591
_publ_contact_author             'Ekaterina Budynina'
_publ_section_title
;
 Nucleophilic Ring Opening of Donor-Acceptor Cyclopropanes with the
 Cyanate Ion: Access to Spiro[pyrrolidone-3,3'-oxindoles].
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8695
_journal_page_last               8709
_journal_paper_doi               10.1021/acs.joc.8b00922
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C19 H18 N2 O2'
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_chemical_melting_point_gt       507
_chemical_melting_point_lt       508
_chemical_name_systematic
;
1-Methyl-5'-(4-tolyl)-2'H-spiro[indole-3,3'-pyrrolidine]-2,2'(1H)-dione
;
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.776(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8738(8)
_cell_length_b                   13.7470(18)
_cell_length_c                   20.081(3)
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.020
_cell_measurement_theta_min      2.503
_cell_volume                     1610.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16406
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.043
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_transmission_factor_max   0.972
_exptl_transmission_factor_min   0.952
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.9185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2990
_reflns_number_total             3888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00922_si_002.cif
_cod_data_source_block           2q
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035591
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              35713
_shelx_hkl_checksum              79061