Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to Iminooxindoles: Access to Spiro[oxindole-3,2'-pyrrolidines].
Akaev, Andrey A.; Bezzubov, Stanislav I.; Desyatkin, Victor G.; Vorobyeva, Nataliya S.; Majouga, Alexander G.; Melnikov, Mikhail Ya; Budynina, Ekaterina M.; The Journal of organic chemistry 84 (2019) 3340–3356; doi:10.1021/acs.joc.8b03208

data_4033919
_publ_contact_author             'Ekaterina Budynina'
_publ_section_title
;
 Stereocontrolled [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes to
 Iminooxindoles: Access to Spiro[oxindole-3,2'-pyrrolidines].
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3340
_journal_page_last               3356
_journal_paper_doi               10.1021/acs.joc.8b03208
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C27 H23 Br N2 O5'
_chemical_formula_sum            'C27 H23 Br N2 O5'
_chemical_formula_weight         535.38
_chemical_melting_point_gt       476
_chemical_melting_point_lt       477
_chemical_name_systematic
;
Dimethyl (3RS,5&#x0092;RS)-5-bromo-2-oxo-1&#x0092;,5&#x0092;-diphenylspiro[indoline-3,2&#x0092;-pyrrolidine]-3&#x0092;,3&#x0092;-dicarboxylate
;
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                80.486(5)
_cell_angle_beta                 67.315(5)
_cell_angle_gamma                81.251(5)
_cell_formula_units_Z            4
_cell_length_a                   13.2965(18)
_cell_length_b                   13.7790(19)
_cell_length_c                   14.0142(19)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.53
_cell_measurement_theta_min      2.31
_cell_volume                     2325.3(6)
_computing_cell_refinement       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker AXS, 2016)'
_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      120
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53555
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.499
_diffrn_reflns_theta_min         2.311
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.811
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0948 before and 0.0490 after correction. The Ratio of minimum to maximum transmission is 0.8335. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.072
_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     635
_refine_ls_number_reflns         14159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.9468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11411
_reflns_number_total             14159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03208_si_004.cif
_cod_data_source_block           3f
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' 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_database_code               4033919
_shelx_shelxl_version_number     2014/7
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), C54(H54), C37(H37), C50(H50), C23(H23), C53(H53), C10(H10),
 C52(H52), C34(H34), C35(H35), C24(H24), C51(H51), C8(H8), C44(H44), C17(H17),
 C25(H25), C48(H48), C19(H19), C7(H7), C45(H45), C47(H47), C18(H18), C27(H27),
 C46(H46), C20(H20), C21(H21), C26(H26)
2.d Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C40(H40A,H40B,
 H40C)
;
_shelx_res_checksum              6424
_shelx_hkl_checksum              35406
_olex2_submission_special_instructions 'No special instructions were received'