Enantioselective organocatalytic formal [3+2]-cycloaddition of isatin-derived ketimines with benzylidenemalononitriles and benzylidineindanones
Duffy, Conor; Roe, William E.; Harkin, Aislinn M.; McNamee, Ryan; Knipe, Peter C.; New Journal of Chemistry 45 (2021) 22034–22038; doi:10.1039/D1NJ04002B

data_7061037
_publ_section_title
;
 Enantioselective organocatalytic formal [3+2]-cycloaddition of
 isatin-derived ketimines with benzylidenemalononitriles and
 benzylidineindanones
;
_journal_issue                   47
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              22034
_journal_page_last               22038
_journal_paper_doi               10.1039/D1NJ04002B
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C33 H23 F3 N2 O3'
_chemical_formula_sum            'C33 H23 F3 N2 O3'
_chemical_formula_weight         552.53
_chemical_melting_point          ?
_chemical_name_common
(2'R,4'S,5'S)-1''-benzyl-4'-phenyl-5'-(trifluoromethyl)dispiro[indene-2,3'-pyrrolidine-2',3''-indoline]-1,2'',3-trione
_chemical_name_systematic        5a
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2021-03-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7809 '
_audit_update_record
;
2021-08-17 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.6178(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.52763(10)
_cell_length_b                   22.8402(2)
_cell_length_c                   12.17728(14)
_cell_measurement_reflns_used    8977
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.19
_cell_measurement_theta_min      5.02
_cell_volume                     2637.21(5)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_pressure         100
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_av_unetI/netI     0.067
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15149
_diffrn_reflns_theta_full        69.381
_diffrn_reflns_theta_max         71.526
_diffrn_reflns_theta_min         3.871
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1144
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol, hexane'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5074
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.0018421
_refine_ls_shift/su_mean         0.0003162
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 0.90P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1231
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1231
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4646
_reflns_number_total             5075
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.50
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0489
_oxford_refine_ls_scale          4.88(10)
_oxford_reflns_number_all        5075
_oxford_structure_analysis_title
'xcalibur in C:\Users\peter\Documents\WR-1.13'
_cod_data_source_file            d1nj04002b2.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7061037--7061039.cif.
;
_cod_original_cell_volume        2637.20(5)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               7061037
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0489
_oxford_refine_ls_wr_factor_all  0.1231