Chiral phosphoric acid-catalyzed Friedel-Crafts reaction of 2,5-disubstituted and 2-monosubstituted pyrroles with isoindolinone-derived ketimines.
Beriša, Arben; Gredičak, Matija; Organic & biomolecular chemistry 21 (2023) 3381–3387; doi:10.1039/d3ob00326d

data_7159268
_publ_section_title
;
 Chiral phosphoric acid-catalyzed Friedel-Crafts reaction of
 2,5-disubstituted and 2-monosubstituted pyrroles with
 isoindolinone-derived ketimines.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3381
_journal_page_last               3387
_journal_paper_doi               10.1039/d3ob00326d
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration R
_chemical_formula_moiety         'C30 H20 F2 N2 O'
_chemical_formula_sum            'C31 H19 F2 N O'
_chemical_formula_weight         459.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-10-26 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.43750(10)
_cell_length_b                   14.8172(2)
_cell_length_c                   21.9398(3)
_cell_measurement_reflns_used    8467
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      79.3310
_cell_measurement_theta_min      3.5850
_cell_volume                     2417.83(6)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_computing_structure_solution
;
SHELXT, Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  XtaLab
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11789
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.655
_diffrn_reflns_theta_min         3.600
_exptl_absorpt_coefficient_mu    0.707
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       needles
_exptl_crystal_F_000             952
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       0.0026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0495P)^2^+0.1205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.623
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                4459
_reflns_number_total             4787
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00326d2.cif
_cod_data_source_block           arb_2a_auto
_cod_depositor_comments          'Adding full bibliography for 7159268.cif.'
_cod_database_code               7159268
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N14(H14), N9(H9), C11(H11), C32(H32), C3(H3), C22(H22), C26(H26), C28(H28),
 C4(H4), C20(H20), C30(H30), C6(H6), C16(H16), C25(H25), C24(H24), C23(H23),
 C5(H5), C18(H18), C19(H19), C17(H17)
;
_shelx_res_checksum              21137
_shelx_shelxl_version_number     2016/6