Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of naphthols and electron-rich phenols with 2-aryl-3<i>H</i>-indol-3-ones.
Ma, Tao; He, Yonghui; Qiao, Xiu-Xiu; Zou, Chang-Peng; Wu, Xi-Xi; Li, Ganpeng; Zhao, Xiao-Jing; Organic & biomolecular chemistry 21 (2023) 489–493; doi:10.1039/d2ob02179j

data_7159030
_publ_section_title
;
 Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts
 reaction of naphthols and electron-rich phenols with
 2-aryl-3<i>H</i>-indol-3-ones.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              489
_journal_page_last               493
_journal_paper_doi               10.1039/d2ob02179j
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H17 N O2'
_chemical_formula_sum            'C24 H17 N O2'
_chemical_formula_weight         351.38
_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_update_record
;
2022-10-20 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6357(6)
_cell_length_b                   12.2218(8)
_cell_length_c                   14.9472(10)
_cell_measurement_reflns_used    9544
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      70.0286
_cell_measurement_theta_min      2.9564
_cell_volume                     1760.3(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14760
_diffrn_reflns_theta_full        70.16
_diffrn_reflns_theta_max         70.16
_diffrn_reflns_theta_min         4.67
_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.225
_refine_ls_abs_structure_details
;

Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0464P)^2^+0.2115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                3180
_reflns_number_total             3343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02179j2.cif
_cod_data_source_block           md_zxj372
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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

 Adding full bibliography for 7159030.cif.
;
_cod_database_code               7159030
_shelx_res_checksum              98822