Organocatalytic Domino Reaction of Spiroaziridine Oxindoles and Malononitrile for the Enantiopure Synthesis of Spiro[dihydropyrrole-3,3'-oxindoles].
Hajra, Saumen; Abu Saleh, S. K.; Hazra, Atanu; Singh, Maya Shankar; The Journal of organic chemistry 84 (2019) 8194–8201; doi:10.1021/acs.joc.9b01226

data_4034649
_publ_section_title
;
 Organocatalytic Domino Reaction of Spiroaziridine Oxindoles and
 Malononitrile for the Enantiopure Synthesis of
 Spiro[dihydropyrrole-3,3'-oxindoles].
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8194
_journal_page_last               8201
_journal_paper_doi               10.1021/acs.joc.9b01226
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C17 H19 Cl N4 O3 S'
_chemical_formula_sum            'C17 H19 Cl N4 O3 S'
_chemical_formula_weight         394.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.8010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8449(4)
_cell_length_b                   18.7623(8)
_cell_length_c                   11.3664(5)
_cell_measurement_reflns_used    43695
_cell_measurement_temperature    273.0(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.786
_cell_volume                     1876.60(14)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.0(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\ w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43695
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.786
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1707 before and 0.0740 after correction. The Ratio of minimum to maximum transmission is 0.8624. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 3060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         6504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0493P)^2^+0.6428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                6426
_reflns_number_total             6504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01226_si_002.cif
_cod_data_source_block           mono_a
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H19 Cl N4 O3 S)'
_cod_original_formula_sum        'C34 H38 Cl2 N8 O6 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     789.74
_cod_database_code               4034649
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.908
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C23(H23), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C9(H9A,H9B,
 H9C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C26(H26A,
 H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'