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_7061038
_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_formula_moiety         'C31 H21 F3 N4 O'
_chemical_formula_sum            'C31 H21 F3 N4 O'
_chemical_formula_weight         522.52
_chemical_melting_point          ?
_chemical_name_common
(3R,4'S,5'S)-1-benzyl-4'-(naphthalen-2-yl)-2-oxo-5'-(trifluoromethyl)spiro[indoline-3,2'-pyrrolidine]-3',3'-dicarbonitrile
_chemical_name_systematic        3d
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2021-08-17
_audit_creation_method           CRYSTALS_ver_14.61_build_6999
_audit_update_record
;
2021-08-17 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 91.462(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   11.6334(6)
_cell_length_b                   6.6182(4)
_cell_length_c                   16.7064(9)
_cell_measurement_reflns_used    19017
_cell_measurement_temperature    150
_cell_measurement_theta_max      71
_cell_measurement_theta_min      4
_cell_volume                     1285.84(12)
_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    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_pressure         100
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_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  0.108
_diffrn_reflns_av_unetI/netI     0.052
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39351
_diffrn_reflns_theta_full        69.307
_diffrn_reflns_theta_max         74.523
_diffrn_reflns_theta_min         3.801
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.59
_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    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol, hexane'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.52
_refine_diff_density_min         -0.66
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1925 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.6196
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         4910
_refine_ls_number_restraints     127
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.1081
_refine_ls_shift/su_max          0.0116005
_refine_ls_shift/su_mean         0.0007826
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.20P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3538
_refine_ls_wR_factor_gt          0.3428
_refine_ls_wR_factor_ref         0.3538
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              7
_reflns_limit_k_min              -8
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4258
_reflns_number_total             4910
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.40
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.1160
_oxford_refine_ls_scale          9.4(12)
_oxford_reflns_number_all        4910
_oxford_structure_analysis_title
'P:\X-Ray\WR-2.190-02\WR-2.190-02.cif_od At 1'
_cod_data_source_file            d1nj04002b2.cif
_cod_data_source_block           'global_CCDC1'
_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_database_code               7061038
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)