Enantioselective construction of a tetrasubstituted stereocenter in isoindolinones via an organocatalyzed reaction between ketones and 3-hydroxyisoindolinones
Matišić, Mateja; Gredičak, Matija; Chemical Communications  (2021) –; doi:10.1039/D1CC05761H

data_7129319
_publ_section_title
;
 Enantioselective construction of a tetrasubstituted stereocenter in
 isoindolinones via an organocatalyzed reaction between ketones and
 3-hydroxyisoindolinones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05761H
_journal_year                    2021
_chemical_absolute_configuration R,S
_chemical_formula_moiety         'C29 H18 F3 N O2'
_chemical_formula_sum            'C29 H18 F3 N O2'
_chemical_formula_weight         469.44
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc28l3bb
_audit_creation_date             2021-02-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-08-12 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.9864(2)
_cell_length_b                   12.9864(2)
_cell_length_c                   28.7740(6)
_cell_measurement_reflns_used    7242
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.181
_cell_measurement_theta_min      4.202
_cell_volume                     4852.64(15)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  Xcalibur
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            25662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.552
_diffrn_reflns_theta_min         3.734
_exptl_absorpt_coefficient_mu    0.807
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       needle
_exptl_crystal_F_000             1936
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0569
_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^)+(0.1044P)^2^+0.6577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3776
_reflns_number_total             4586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05761h2.cif
_cod_data_source_block           exp_812
_cod_original_cell_volume        4852.64(18)
_cod_database_code               7129319
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q),
 C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W), C00Y(H00Y)
;
_shelx_res_checksum              50349
_olex2_submission_special_instructions 'No special instructions were received'