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_7061039
_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_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C29 H24 F3 N3 O3'
_chemical_formula_sum            'C29 H24 F3 N3 O3'
_chemical_formula_weight         519.51
_chemical_melting_point          ?
_chemical_name_common            '(-)-3l (major)'
_chemical_name_systematic
'ethyl (3R,3'S,4'S,5'S)-1-benzyl-3'-cyano-2-oxo-4'-phenyl-5'-(trifluoromethyl)spiro[indoline-3,2'-pyrrolidine]-3'-carboxylate'
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2021-10-18
_audit_creation_method           CRYSTALS_ver_14.61_build_6999
_audit_update_record
;
2021-10-18 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.847500(10)
_cell_length_b                   13.547100(10)
_cell_length_c                   15.256700(14)
_cell_measurement_reflns_used    18379
_cell_measurement_temperature    100
_cell_measurement_theta_max      71
_cell_measurement_theta_min      4
_cell_volume                     2448.689(4)
_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    'USER DEFINED STRUCTURE SOLUTION'
_diffrn_ambient_pressure         100
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.000
_diffrn_reflns_av_unetI/netI     0.032
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22989
_diffrn_reflns_theta_full        70.066
_diffrn_reflns_theta_max         71.496
_diffrn_reflns_theta_min         4.364
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.55
_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    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.31
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 2037 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9360
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.0007287
_refine_ls_shift/su_mean         0.0001634
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.79P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0642
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0642
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                4681
_reflns_number_total             4737
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.89
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0258
_oxford_refine_ls_scale          5.12(5)
_oxford_reflns_number_all        4737
_oxford_structure_analysis_title
'P:\X-Ray\WR 2.166\02\WR-2-166-02.cif_od At 1'
_cod_data_source_file            d1nj04002b2.cif
_cod_data_source_block           'global_CCDC2'
_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_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               7061039
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  0.03(3)
_oxford_bijvoet_difference       0.04(3)