#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:29:05 +0300 (Fri, 05 May 2023) $
#$Revision: 283491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159030.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159030
loop_
_publ_author_name
'Ma, Tao'
'He, Yonghui'
'Qiao, Xiu-Xiu'
'Zou, Chang-Peng'
'Wu, Xi-Xi'
'Li, Ganpeng'
'Zhao, Xiao-Jing'
_publ_section_title
;
 Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts
 reaction of naphthols and electron-rich phenols with
 2-aryl-3H-indol-3-ones.
;
_journal_issue                   3
_journal_name_full               'Organic & 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/[σ²(Fo²)+(0.0464P)²+0.2115P] where P=(Fo²+2Fc²)/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 > 2σ(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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.01736(14) 0.50542(12) 0.37504(9) 0.0318(3) Uani d . . . 1 . .
O O2 0.09739(17) 0.31409(13) 0.31453(9) 0.0317(3) Uani d . . . 1 . .
H H4 0.078966 0.380624 0.322118 0.047 Uiso calc U . R 1 . .
N N1 0.31658(18) 0.51420(15) 0.51218(10) 0.0281(4) Uani d . . . 1 . .
H H1 0.397381 0.494235 0.534231 0.034 Uiso calc U . R 1 . .
C C1 0.5163(2) 0.5222(2) 0.20759(15) 0.0413(5) Uani d . . . 1 . .
H H5 0.577396 0.536262 0.159053 0.05 Uiso calc U . R 1 . .
C C2 0.5481(2) 0.4423(2) 0.26969(17) 0.0429(6) Uani d . . . 1 . .
H H8 0.631284 0.401205 0.2638 0.051 Uiso calc U . R 1 . .
C C3 0.4591(2) 0.4221(2) 0.34048(15) 0.0355(5) Uani d . . . 1 . .
H H9 0.4816 0.366802 0.382738 0.043 Uiso calc U . R 1 . .
C C4 0.3368(2) 0.48185(17) 0.35052(13) 0.0272(4) Uani d . . . 1 . .
C C5 0.2489(2) 0.46230(16) 0.43478(12) 0.0264(4) Uani d . . . 1 . .
C C6 0.2272(2) 0.33936(17) 0.45133(13) 0.0260(4) Uani d . . . 1 . .
C C7 0.1604(2) 0.27385(18) 0.38911(12) 0.0269(4) Uani d . . . 1 . .
C C8 0.1588(2) 0.15777(18) 0.39806(13) 0.0276(4) Uani d . . . 1 . .
C C9 0.2182(2) 0.10980(18) 0.47566(13) 0.0289(4) Uani d . . . 1 . .
C C10 0.2149(2) -0.00564(18) 0.48479(14) 0.0337(5) Uani d . . . 1 . .
H H13 0.250146 -0.038607 0.537666 0.04 Uiso calc U . R 1 . .
C C11 0.1613(2) -0.07027(18) 0.41826(15) 0.0352(5) Uani d . . . 1 . .
H H2 0.161339 -0.147621 0.424506 0.042 Uiso calc U . R 1 . .
C C12 0.1687(3) 0.74388(18) 0.63987(15) 0.0368(5) Uani d . . . 1 . .
H H3 0.187158 0.792 0.68834 0.044 Uiso calc U . R 1 . .
C C13 0.2685(2) 0.66872(17) 0.61603(13) 0.0320(4) Uani d . . . 1 . .
H H17 0.355057 0.665225 0.646303 0.038 Uiso calc U . R 1 . .
C C14 0.2372(2) 0.59746(16) 0.54519(12) 0.0266(4) Uani d . . . 1 . .
C C15 0.3958(3) 0.5811(2) 0.21651(14) 0.0398(5) Uani d . . . 1 . .
H H7 0.373757 0.635903 0.173726 0.048 Uiso calc U . R 1 . .
C C16 0.3052(2) 0.56159(19) 0.28758(13) 0.0336(5) Uani d . . . 1 . .
H H6 0.221948 0.602781 0.292888 0.04 Uiso calc U . R 1 . .
C C17 0.1085(2) 0.52450(17) 0.43063(12) 0.0266(4) Uani d . . . 1 . .
C C18 0.1098(2) 0.60508(16) 0.50067(13) 0.0272(4) Uani d . . . 1 . .
C C19 0.0105(2) 0.68309(17) 0.52570(14) 0.0325(5) Uani d . . . 1 . .
H H10 -0.075689 0.688026 0.495139 0.039 Uiso calc U . R 1 . .
C C20 0.0408(3) 0.75229(18) 0.59550(15) 0.0380(5) Uani d . . . 1 . .
H H11 -0.024834 0.80583 0.613702 0.046 Uiso calc U . R 1 . .
C C21 0.2861(2) 0.28842(18) 0.52819(13) 0.0285(4) Uani d . . . 1 . .
H H12 0.330844 0.332557 0.571854 0.034 Uiso calc U . R 1 . .
C C22 0.2801(2) 0.17799(18) 0.54074(13) 0.0307(4) Uani d . . . 1 . .
H H16 0.317798 0.146694 0.593609 0.037 Uiso calc U . R 1 . .
C C23 0.1061(2) -0.02143(19) 0.34043(15) 0.0348(5) Uani d . . . 1 . .
H H14 0.070838 -0.066627 0.293979 0.042 Uiso calc U . R 1 . .
C C24 0.1025(2) 0.08948(19) 0.33075(14) 0.0317(4) Uani d . . . 1 . .
H H15 0.062122 0.120941 0.278772 0.038 Uiso calc U . R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O2 H4 . . 109.5 ?
C14 N1 C5 . . 110.93(16) ?
C14 N1 H1 . . 124.5 ?
C5 N1 H1 . . 124.5 ?
C15 C1 C2 . . 119.5(2) ?
C15 C1 H5 . . 120.2 ?
C2 C1 H5 . . 120.2 ?
C1 C2 C3 . . 120.2(2) ?
C1 C2 H8 . . 119.9 ?
C3 C2 H8 . . 119.9 ?
C2 C3 C4 . . 120.8(2) ?
C2 C3 H9 . . 119.6 ?
C4 C3 H9 . . 119.6 ?
C16 C4 C3 . . 118.73(19) ?
C16 C4 C5 . . 122.90(19) ?
C3 C4 C5 . . 118.20(18) ?
N1 C5 C4 . . 109.46(15) ?
N1 C5 C6 . . 110.80(15) ?
C4 C5 C6 . . 111.05(16) ?
N1 C5 C17 . . 101.91(15) ?
C4 C5 C17 . . 111.81(16) ?
C6 C5 C17 . . 111.46(16) ?
C7 C6 C21 . . 118.28(19) ?
C7 C6 C5 . . 121.34(17) ?
C21 C6 C5 . . 120.16(17) ?
O2 C7 C6 . . 123.23(19) ?
O2 C7 C8 . . 115.56(18) ?
C6 C7 C8 . . 121.16(18) ?
C24 C8 C9 . . 119.5(2) ?
C24 C8 C7 . . 121.64(19) ?
C9 C8 C7 . . 118.89(18) ?
C22 C9 C10 . . 122.02(19) ?
C22 C9 C8 . . 119.28(19) ?
C10 C9 C8 . . 118.69(19) ?
C11 C10 C9 . . 120.8(2) ?
C11 C10 H13 . . 119.6 ?
C9 C10 H13 . . 119.6 ?
C10 C11 C23 . . 119.7(2) ?
C10 C11 H2 . . 120.1 ?
C23 C11 H2 . . 120.1 ?
C13 C12 C20 . . 122.7(2) ?
C13 C12 H3 . . 118.7 ?
C20 C12 H3 . . 118.7 ?
C12 C13 C14 . . 117.3(2) ?
C12 C13 H17 . . 121.3 ?
C14 C13 H17 . . 121.3 ?
N1 C14 C18 . . 111.66(17) ?
N1 C14 C13 . . 127.93(19) ?
C18 C14 C13 . . 120.39(19) ?
C1 C15 C16 . . 120.9(2) ?
C1 C15 H7 . . 119.6 ?
C16 C15 H7 . . 119.6 ?
C4 C16 C15 . . 119.9(2) ?
C4 C16 H6 . . 120.1 ?
C15 C16 H6 . . 120.1 ?
O1 C17 C18 . . 128.85(19) ?
O1 C17 C5 . . 123.76(18) ?
C18 C17 C5 . . 107.38(16) ?
C14 C18 C19 . . 121.13(19) ?
C14 C18 C17 . . 107.96(17) ?
C19 C18 C17 . . 130.9(2) ?
C20 C19 C18 . . 118.4(2) ?
C20 C19 H10 . . 120.8 ?
C18 C19 H10 . . 120.8 ?
C19 C20 C12 . . 120.0(2) ?
C19 C20 H11 . . 120.0 ?
C12 C20 H11 . . 120.0 ?
C22 C21 C6 . . 121.76(19) ?
C22 C21 H12 . . 119.1 ?
C6 C21 H12 . . 119.1 ?
C21 C22 C9 . . 120.45(19) ?
C21 C22 H16 . . 119.8 ?
C9 C22 H16 . . 119.8 ?
C24 C23 C11 . . 121.2(2) ?
C24 C23 H14 . . 119.4 ?
C11 C23 H14 . . 119.4 ?
C23 C24 C8 . . 120.1(2) ?
C23 C24 H15 . . 120.0 ?
C8 C24 H15 . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C17 . 1.231(2) ?
O2 C7 . 1.361(2) ?
O2 H4 . 0.84 ?
N1 C14 . 1.365(3) ?
N1 C5 . 1.472(2) ?
N1 H1 . 0.88 ?
C1 C15 . 1.373(4) ?
C1 C2 . 1.381(4) ?
C1 H5 . 0.95 ?
C2 C3 . 1.384(3) ?
C2 H8 . 0.95 ?
C3 C4 . 1.394(3) ?
C3 H9 . 0.95 ?
C4 C16 . 1.389(3) ?
C4 C5 . 1.536(3) ?
C5 C6 . 1.537(3) ?
C5 C17 . 1.553(3) ?
C6 C7 . 1.386(3) ?
C6 C21 . 1.425(3) ?
C7 C8 . 1.425(3) ?
C8 C24 . 1.415(3) ?
C8 C9 . 1.420(3) ?
C9 C22 . 1.413(3) ?
C9 C10 . 1.418(3) ?
C10 C11 . 1.371(3) ?
C10 H13 . 0.95 ?
C11 C23 . 1.412(3) ?
C11 H2 . 0.95 ?
C12 C13 . 1.377(3) ?
C12 C20 . 1.403(4) ?
C12 H3 . 0.95 ?
C13 C14 . 1.404(3) ?
C13 H17 . 0.95 ?
C14 C18 . 1.399(3) ?
C15 C16 . 1.396(3) ?
C15 H7 . 0.95 ?
C16 H6 . 0.95 ?
C17 C18 . 1.437(3) ?
C18 C19 . 1.401(3) ?
C19 C20 . 1.374(3) ?
C19 H10 . 0.95 ?
C20 H11 . 0.95 ?
C21 C22 . 1.364(3) ?
C21 H12 . 0.95 ?
C22 H16 . 0.95 ?
C23 C24 . 1.364(3) ?
C23 H14 . 0.95 ?
C24 H15 . 0.95 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H4 O1 . 0.84 1.82 2.623(2) 160.1 ?
C13 H17 O2 4_565 0.95 2.57 3.243(2) 128.2 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 C1 C2 C3 . . . . -0.1(4) ?
C1 C2 C3 C4 . . . . -0.3(4) ?
C2 C3 C4 C16 . . . . 0.6(3) ?
C2 C3 C4 C5 . . . . -174.8(2) ?
C14 N1 C5 C4 . . . . 114.86(18) ?
C14 N1 C5 C6 . . . . -122.34(17) ?
C14 N1 C5 C17 . . . . -3.6(2) ?
C16 C4 C5 N1 . . . . -100.7(2) ?
C3 C4 C5 N1 . . . . 74.6(2) ?
C16 C4 C5 C6 . . . . 136.67(19) ?
C3 C4 C5 C6 . . . . -48.1(2) ?
C16 C4 C5 C17 . . . . 11.5(3) ?
C3 C4 C5 C17 . . . . -173.29(18) ?
N1 C5 C6 C7 . . . . 177.52(17) ?
C4 C5 C6 C7 . . . . -60.6(2) ?
C17 C5 C6 C7 . . . . 64.8(2) ?
N1 C5 C6 C21 . . . . -7.9(2) ?
C4 C5 C6 C21 . . . . 114.02(19) ?
C17 C5 C6 C21 . . . . -120.60(19) ?
C21 C6 C7 O2 . . . . 178.26(18) ?
C5 C6 C7 O2 . . . . -7.0(3) ?
C21 C6 C7 C8 . . . . -4.3(3) ?
C5 C6 C7 C8 . . . . 170.38(17) ?
O2 C7 C8 C24 . . . . 3.7(3) ?
C6 C7 C8 C24 . . . . -173.92(18) ?
O2 C7 C8 C9 . . . . -177.84(17) ?
C6 C7 C8 C9 . . . . 4.6(3) ?
C24 C8 C9 C22 . . . . 177.06(18) ?
C7 C8 C9 C22 . . . . -1.5(3) ?
C24 C8 C9 C10 . . . . -2.2(3) ?
C7 C8 C9 C10 . . . . 179.24(17) ?
C22 C9 C10 C11 . . . . -176.21(19) ?
C8 C9 C10 C11 . . . . 3.1(3) ?
C9 C10 C11 C23 . . . . -1.3(3) ?
C20 C12 C13 C14 . . . . -1.1(3) ?
C5 N1 C14 C18 . . . . 4.3(2) ?
C5 N1 C14 C13 . . . . -177.36(19) ?
C12 C13 C14 N1 . . . . -177.2(2) ?
C12 C13 C14 C18 . . . . 0.9(3) ?
C2 C1 C15 C16 . . . . 0.2(3) ?
C3 C4 C16 C15 . . . . -0.6(3) ?
C5 C4 C16 C15 . . . . 174.64(19) ?
C1 C15 C16 C4 . . . . 0.2(3) ?
N1 C5 C17 O1 . . . . -179.05(18) ?
C4 C5 C17 O1 . . . . 64.1(2) ?
C6 C5 C17 O1 . . . . -60.8(2) ?
N1 C5 C17 C18 . . . . 1.80(19) ?
C4 C5 C17 C18 . . . . -115.02(17) ?
C6 C5 C17 C18 . . . . 120.02(17) ?
N1 C14 C18 C19 . . . . 178.13(18) ?
C13 C14 C18 C19 . . . . -0.3(3) ?
N1 C14 C18 C17 . . . . -3.0(2) ?
C13 C14 C18 C17 . . . . 178.57(18) ?
O1 C17 C18 C14 . . . . -178.6(2) ?
C5 C17 C18 C14 . . . . 0.5(2) ?
O1 C17 C18 C19 . . . . 0.2(4) ?
C5 C17 C18 C19 . . . . 179.3(2) ?
C14 C18 C19 C20 . . . . -0.2(3) ?
C17 C18 C19 C20 . . . . -178.8(2) ?
C18 C19 C20 C12 . . . . 0.0(3) ?
C13 C12 C20 C19 . . . . 0.6(3) ?
C7 C6 C21 C22 . . . . 1.0(3) ?
C5 C6 C21 C22 . . . . -173.75(18) ?
C6 C21 C22 C9 . . . . 2.0(3) ?
C10 C9 C22 C21 . . . . 177.52(19) ?
C8 C9 C22 C21 . . . . -1.7(3) ?
C10 C11 C23 C24 . . . . -1.3(3) ?
C11 C23 C24 C8 . . . . 2.1(3) ?
C9 C8 C24 C23 . . . . -0.3(3) ?
C7 C8 C24 C23 . . . . 178.2(2) ?
