# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X230627TM_5TMSADPQN_lt
_audit_block_doi                 10.5517/ccdc.csd.cc2pcmtj
_database_code_depnum_ccdc_archive 'CCDC 2483838'
loop_
_audit_author_name
_audit_author_address
'Masaomi Takii'
;Keio University
Japan
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_audit_creation_method           'APEX4 v2021.10-0'
_chemical_name_systematic        
;
5-[2-(trimethylsilyl)ethynyl]-2,2-diphenyl-1,2-dihydroquinoline N-oxyl
;
_chemical_name_common            ?
_chemical_formula_moiety         'C26 H24 N O Si'
_chemical_formula_sum            'C26 H24 N O Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         394.55

_chemical_melting_point          413

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8542(3)
_cell_length_b                   9.0975(2)
_cell_length_c                   22.1134(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.2990(10)
_cell_angle_gamma                90
_cell_volume                     2179.99(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7658
_cell_measurement_theta_min      2.4214
_cell_measurement_theta_max      25.0188
_cell_measurement_temperature    90.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark black-red'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.072
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836

_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.(2)

_diffrn_source                   'micro focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            22134
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             3841
_reflns_number_gt                2779
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.2123
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_number_reflns         3841
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0878P)²+3.8063P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.503
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.005(2)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       APEX4(Bruker)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'

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
Si Si1 0.24978(8) 0.26423(11) 0.54205(4) 0.0340(3) Uani d . . . 1 . .
O O1 0.5926(2) 0.3688(3) 0.18704(11) 0.0456(7) Uani d . . . 1 . .
N N1 0.5163(2) 0.3722(3) 0.22922(12) 0.0347(7) Uani d . . . 1 . .
C C5 0.4993(3) 0.2468(3) 0.38723(14) 0.0293(7) Uani d . . . 1 . .
C C4 0.4642(3) 0.3110(4) 0.33126(14) 0.0287(7) Uani d . . . 1 . .
C C9 0.5469(3) 0.3027(4) 0.28429(14) 0.0302(7) Uani d . . . 1 . .
C C22 0.4199(3) 0.2572(4) 0.43719(14) 0.0310(7) Uani d . . . 1 . .
C C10 0.3272(3) 0.3800(4) 0.16123(14) 0.0332(8) Uani d . . . 1 . .
C C16 0.4377(3) 0.6140(4) 0.20131(14) 0.0315(7) Uani d . . . 1 . .
C C3 0.3465(3) 0.3843(4) 0.31982(14) 0.0339(8) Uani d . . . 1 . .
H H3 0.288811 0.384921 0.350559 0.041000 Uiso calc U . R 1 . .
C C1 0.3982(3) 0.4551(4) 0.21469(14) 0.0327(7) Uani d . . . 1 . .
C C8 0.6585(3) 0.2275(4) 0.29184(15) 0.0333(7) Uani d . . . 1 . .
H H8 0.713113 0.222616 0.259817 0.040000 Uiso calc U . R 1 . .
C C2 0.3173(3) 0.4505(4) 0.26745(15) 0.0353(8) Uani d . . . 1 . .
H H2 0.239603 0.498486 0.263048 0.042000 Uiso calc U . R 1 . .
C C23 0.3531(3) 0.2633(4) 0.47897(14) 0.0335(8) Uani d . . . 1 . .
C C6 0.6116(3) 0.1709(4) 0.39449(15) 0.0377(8) Uani d . . . 1 . .
H H6 0.635046 0.126597 0.432310 0.045000 Uiso calc U . R 1 . .
C C17 0.4618(3) 0.6572(4) 0.14323(15) 0.0378(8) Uani d . . . 1 . .
H H17 0.447062 0.591040 0.110373 0.045000 Uiso calc U . R 1 . .
C C15 0.2268(3) 0.4516(4) 0.13250(15) 0.0376(8) Uani d . . . 1 . .
H H15 0.206492 0.548431 0.144556 0.045000 Uiso calc U . R 1 . .
C C7 0.6885(3) 0.1602(4) 0.34681(15) 0.0375(8) Uani d . . . 1 . .
H H7 0.762975 0.105627 0.351949 0.045000 Uiso calc U . R 1 . .
C C21 0.4596(3) 0.7126(4) 0.24884(16) 0.0405(8) Uani d . . . 1 . .
H H21 0.443137 0.684096 0.288908 0.049000 Uiso calc U . R 1 . .
C C19 0.5312(3) 0.8931(4) 0.18048(17) 0.0417(8) Uani d . . . 1 . .
H H19 0.565320 0.987343 0.173471 0.050000 Uiso calc U . R 1 . .
C C11 0.3536(4) 0.2379(4) 0.14353(16) 0.0418(9) Uani d . . . 1 . .
H H11 0.421115 0.186967 0.163099 0.050000 Uiso calc U . R 1 . .
C C20 0.5050(3) 0.8512(4) 0.23830(17) 0.0429(9) Uani d . . . 1 . .
H H20 0.518250 0.918129 0.270994 0.051000 Uiso calc U . R 1 . .
C C18 0.5074(3) 0.7968(4) 0.13276(17) 0.0434(9) Uani d . . . 1 . .
H H18 0.522335 0.826481 0.092652 0.052000 Uiso calc U . R 1 . .
C C14 0.1561(3) 0.3833(4) 0.08656(17) 0.0438(9) Uani d . . . 1 . .
H H14 0.088433 0.433947 0.066977 0.053000 Uiso calc U . R 1 . .
C C24 0.1450(3) 0.1028(5) 0.53362(15) 0.0440(9) Uani d . . . 1 . .
H H24A 0.085396 0.118703 0.499239 0.066000 Uiso calc U . R 1 . .
H H24B 0.100756 0.090341 0.570697 0.066000 Uiso calc U . R 1 . .
H H24C 0.193500 0.014281 0.526490 0.066000 Uiso calc U . R 1 . .
C C25 0.3453(3) 0.2609(5) 0.61394(15) 0.0469(10) Uani d . . . 1 . .
H H25A 0.397349 0.172860 0.615263 0.070000 Uiso calc U . R 1 . .
H H25B 0.291499 0.259374 0.648051 0.070000 Uiso calc U . R 1 . .
H H25C 0.397558 0.348738 0.616629 0.070000 Uiso calc U . R 1 . .
C C12 0.2828(4) 0.1689(4) 0.09764(17) 0.0476(10) Uani d . . . 1 . .
H H12 0.302438 0.071634 0.085888 0.057000 Uiso calc U . R 1 . .
C C13 0.1838(4) 0.2409(4) 0.06898(17) 0.0452(9) Uani d . . . 1 . .
H H13 0.135247 0.193620 0.037593 0.054000 Uiso calc U . R 1 . .
C C26 0.1553(4) 0.4349(5) 0.53783(18) 0.0529(10) Uani d . . . 1 . .
H H26A 0.209140 0.520482 0.544472 0.079000 Uiso calc U . R 1 . .
H H26B 0.094742 0.432080 0.569027 0.079000 Uiso calc U . R 1 . .
H H26C 0.112144 0.441898 0.497767 0.079000 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Si1 C23 . 1.840(3) ?
Si1 C25 . 1.847(4) ?
Si1 C26 . 1.860(4) ?
Si1 C24 . 1.861(4) ?
O1 N1 . 1.283(3) ?
N1 C9 . 1.395(4) ?
N1 C1 . 1.505(4) ?
C5 C6 . 1.402(5) ?
C5 C4 . 1.402(4) ?
C5 C22 . 1.442(4) ?
C4 C9 . 1.414(4) ?
C4 C3 . 1.450(4) ?
C9 C8 . 1.393(5) ?
C22 C23 . 1.208(5) ?
C10 C11 . 1.386(5) ?
C10 C15 . 1.391(5) ?
C10 C1 . 1.534(5) ?
C16 C17 . 1.382(5) ?
C16 C21 . 1.391(5) ?
C16 C1 . 1.542(5) ?
C3 C2 . 1.327(5) ?
C3 H3 . 0.950000 ?
C1 C2 . 1.501(4) ?
C8 C7 . 1.383(5) ?
C8 H8 . 0.950000 ?
C2 H2 . 0.950000 ?
C6 C7 . 1.385(5) ?
C6 H6 . 0.950000 ?
C17 C18 . 1.388(5) ?
C17 H17 . 0.950000 ?
C15 C14 . 1.384(5) ?
C15 H15 . 0.950000 ?
C7 H7 . 0.950000 ?
C21 C20 . 1.378(5) ?
C21 H21 . 0.950000 ?
C19 C20 . 1.379(5) ?
C19 C18 . 1.384(5) ?
C19 H19 . 0.950000 ?
C11 C12 . 1.388(6) ?
C11 H11 . 0.950000 ?
C20 H20 . 0.950000 ?
C18 H18 . 0.950000 ?
C14 C13 . 1.391(5) ?
C14 H14 . 0.950000 ?
C24 H24A . 0.980000 ?
C24 H24B . 0.980000 ?
C24 H24C . 0.980000 ?
C25 H25A . 0.980000 ?
C25 H25B . 0.980000 ?
C25 H25C . 0.980000 ?
C12 C13 . 1.380(6) ?
C12 H12 . 0.950000 ?
C13 H13 . 0.950000 ?
C26 H26A . 0.980000 ?
C26 H26B . 0.980000 ?
C26 H26C . 0.980000 ?

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
C23 Si1 C25 . . 108.42(16) ?
C23 Si1 C26 . . 108.92(16) ?
C25 Si1 C26 . . 109.7(2) ?
C23 Si1 C24 . . 108.45(16) ?
C25 Si1 C24 . . 112.51(18) ?
C26 Si1 C24 . . 108.75(19) ?
O1 N1 C9 . . 119.5(3) ?
O1 N1 C1 . . 115.7(2) ?
C9 N1 C1 . . 124.8(2) ?
C6 C5 C4 . . 119.8(3) ?
C6 C5 C22 . . 119.9(3) ?
C4 C5 C22 . . 120.3(3) ?
C5 C4 C9 . . 118.3(3) ?
C5 C4 C3 . . 122.5(3) ?
C9 C4 C3 . . 119.1(3) ?
C8 C9 N1 . . 119.3(3) ?
C8 C9 C4 . . 121.5(3) ?
N1 C9 C4 . . 119.2(3) ?
C23 C22 C5 . . 178.8(3) ?
C11 C10 C15 . . 118.5(3) ?
C11 C10 C1 . . 122.0(3) ?
C15 C10 C1 . . 119.3(3) ?
C17 C16 C21 . . 119.1(3) ?
C17 C16 C1 . . 120.9(3) ?
C21 C16 C1 . . 119.8(3) ?
C2 C3 C4 . . 121.6(3) ?
C2 C3 H3 . . 119.200000 ?
C4 C3 H3 . . 119.200000 ?
C2 C1 N1 . . 110.4(2) ?
C2 C1 C10 . . 107.2(3) ?
N1 C1 C10 . . 109.0(3) ?
C2 C1 C16 . . 110.9(3) ?
N1 C1 C16 . . 105.6(3) ?
C10 C1 C16 . . 113.7(3) ?
C7 C8 C9 . . 118.8(3) ?
C7 C8 H8 . . 120.600000 ?
C9 C8 H8 . . 120.600000 ?
C3 C2 C1 . . 124.8(3) ?
C3 C2 H2 . . 117.600000 ?
C1 C2 H2 . . 117.600000 ?
C22 C23 Si1 . . 177.5(3) ?
C7 C6 C5 . . 120.4(3) ?
C7 C6 H6 . . 119.800000 ?
C5 C6 H6 . . 119.800000 ?
C16 C17 C18 . . 120.2(3) ?
C16 C17 H17 . . 119.900000 ?
C18 C17 H17 . . 119.900000 ?
C14 C15 C10 . . 120.8(3) ?
C14 C15 H15 . . 119.600000 ?
C10 C15 H15 . . 119.600000 ?
C8 C7 C6 . . 121.1(3) ?
C8 C7 H7 . . 119.500000 ?
C6 C7 H7 . . 119.500000 ?
C20 C21 C16 . . 120.6(3) ?
C20 C21 H21 . . 119.700000 ?
C16 C21 H21 . . 119.700000 ?
C20 C19 C18 . . 119.5(3) ?
C20 C19 H19 . . 120.300000 ?
C18 C19 H19 . . 120.300000 ?
C10 C11 C12 . . 120.9(4) ?
C10 C11 H11 . . 119.500000 ?
C12 C11 H11 . . 119.500000 ?
C21 C20 C19 . . 120.3(3) ?
C21 C20 H20 . . 119.800000 ?
C19 C20 H20 . . 119.800000 ?
C19 C18 C17 . . 120.3(3) ?
C19 C18 H18 . . 119.800000 ?
C17 C18 H18 . . 119.800000 ?
C15 C14 C13 . . 120.2(4) ?
C15 C14 H14 . . 119.900000 ?
C13 C14 H14 . . 119.900000 ?
Si1 C24 H24A . . 109.500000 ?
Si1 C24 H24B . . 109.500000 ?
H24A C24 H24B . . 109.500000 ?
Si1 C24 H24C . . 109.500000 ?
H24A C24 H24C . . 109.500000 ?
H24B C24 H24C . . 109.500000 ?
Si1 C25 H25A . . 109.500000 ?
Si1 C25 H25B . . 109.500000 ?
H25A C25 H25B . . 109.500000 ?
Si1 C25 H25C . . 109.500000 ?
H25A C25 H25C . . 109.500000 ?
H25B C25 H25C . . 109.500000 ?
C13 C12 C11 . . 120.3(4) ?
C13 C12 H12 . . 119.800000 ?
C11 C12 H12 . . 119.800000 ?
C12 C13 C14 . . 119.3(4) ?
C12 C13 H13 . . 120.400000 ?
C14 C13 H13 . . 120.400000 ?
Si1 C26 H26A . . 109.500000 ?
Si1 C26 H26B . . 109.500000 ?
H26A C26 H26B . . 109.500000 ?
Si1 C26 H26C . . 109.500000 ?
H26A C26 H26C . . 109.500000 ?
H26B C26 H26C . . 109.500000 ?

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
C6 C5 C4 C9 . . . . -2.9(5) ?
C22 C5 C4 C9 . . . . 177.7(3) ?
C6 C5 C4 C3 . . . . 176.7(3) ?
C22 C5 C4 C3 . . . . -2.7(5) ?
O1 N1 C9 C8 . . . . -1.7(5) ?
C1 N1 C9 C8 . . . . 179.1(3) ?
O1 N1 C9 C4 . . . . 177.9(3) ?
C1 N1 C9 C4 . . . . -1.3(5) ?
C5 C4 C9 C8 . . . . 2.8(5) ?
C3 C4 C9 C8 . . . . -176.8(3) ?
C5 C4 C9 N1 . . . . -176.9(3) ?
C3 C4 C9 N1 . . . . 3.5(5) ?
C5 C4 C3 C2 . . . . 176.8(3) ?
C9 C4 C3 C2 . . . . -3.7(5) ?
O1 N1 C1 C2 . . . . 179.9(3) ?
C9 N1 C1 C2 . . . . -0.9(5) ?
O1 N1 C1 C10 . . . . 62.4(4) ?
C9 N1 C1 C10 . . . . -118.4(3) ?
O1 N1 C1 C16 . . . . -60.2(4) ?
C9 N1 C1 C16 . . . . 119.1(3) ?
C11 C10 C1 C2 . . . . -102.6(3) ?
C15 C10 C1 C2 . . . . 72.2(4) ?
C11 C10 C1 N1 . . . . 17.0(4) ?
C15 C10 C1 N1 . . . . -168.3(3) ?
C11 C10 C1 C16 . . . . 134.4(3) ?
C15 C10 C1 C16 . . . . -50.8(4) ?
C17 C16 C1 C2 . . . . -150.5(3) ?
C21 C16 C1 C2 . . . . 35.0(4) ?
C17 C16 C1 N1 . . . . 89.9(3) ?
C21 C16 C1 N1 . . . . -84.7(3) ?
C17 C16 C1 C10 . . . . -29.5(4) ?
C21 C16 C1 C10 . . . . 155.9(3) ?
N1 C9 C8 C7 . . . . 179.4(3) ?
C4 C9 C8 C7 . . . . -0.2(5) ?
C4 C3 C2 C1 . . . . 1.4(6) ?
N1 C1 C2 C3 . . . . 0.8(5) ?
C10 C1 C2 C3 . . . . 119.4(4) ?
C16 C1 C2 C3 . . . . -115.9(4) ?
C4 C5 C6 C7 . . . . 0.6(5) ?
C22 C5 C6 C7 . . . . 180.0(3) ?
C21 C16 C17 C18 . . . . 0.2(5) ?
C1 C16 C17 C18 . . . . -174.5(3) ?
C11 C10 C15 C14 . . . . -1.1(5) ?
C1 C10 C15 C14 . . . . -176.0(3) ?
C9 C8 C7 C6 . . . . -2.2(5) ?
C5 C6 C7 C8 . . . . 2.1(5) ?
C17 C16 C21 C20 . . . . -0.2(5) ?
C1 C16 C21 C20 . . . . 174.5(3) ?
C15 C10 C11 C12 . . . . 0.9(5) ?
C1 C10 C11 C12 . . . . 175.7(3) ?
C16 C21 C20 C19 . . . . -1.1(5) ?
C18 C19 C20 C21 . . . . 2.3(5) ?
C20 C19 C18 C17 . . . . -2.4(5) ?
C16 C17 C18 C19 . . . . 1.1(5) ?
C10 C15 C14 C13 . . . . 0.8(5) ?
C10 C11 C12 C13 . . . . -0.4(5) ?
C11 C12 C13 C14 . . . . 0.1(5) ?
C15 C14 C13 C12 . . . . -0.3(5) ?


# start Validation Reply Form
_vrf_PLAT031_X230627TM_5TMSADPQN_lt 
;
PROBLEM: Refined Extinction Parameter Within Range of ...      2.500 Sigma 
RESPONSE: The small value indicates that extinction effects are minor
but the parameter is retained for the best model fit.
;
_vrf_PLAT340_X230627TM_5TMSADPQN_lt 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00488 Ang.  
RESPONSE: RESPONSE: The bond precision is slightly lower than the limit 
due to the thermal motion of the ethynyl group, but it is acceptable 
given the overall data quality.
;
_vrf_PLAT905_X230627TM_5TMSADPQN_lt 
;
PROBLEM: Negative K value in the Analysis of Variance ...     -3.179 Report
RESPONSE: The weighting scheme was optimized by the refinement
program (SHELXL) to minimize the R-values and Goodness of Fit.
The negative K-value is a statistical artifact of the weighting optimization
and does not affect the validity of the structural model.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X240718TM_5EDPQN_lt
_database_code_depnum_ccdc_archive 'CCDC 2483839'
loop_
_audit_author_name
_audit_author_address
'Masaomi Takii'
;Keio University
Japan
;
_audit_update_record             
;
2025-11-26 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_chemical_name_systematic        
'5-ethynyl-2,2-diphenyl-1,2-dihydroquinoline N-oxyl'
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H16 N O'
_chemical_formula_sum            'C23 H16 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         322.37
_chemical_absolute_configuration unk

_chemical_melting_point          404

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7866(5)
_cell_length_b                   12.2573(7)
_cell_length_c                   13.7175(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1645.51(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8887
_cell_measurement_theta_min      2.2282
_cell_measurement_theta_max      25.0324
_cell_measurement_temperature    90.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'dark black-red'
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.(2)

_diffrn_source                   'micro focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            17814
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2921
_reflns_number_gt                2614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1317
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_number_reflns         2921
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.9632P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.010(4)
_refine_ls_abs_structure_details 
;

Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       APEX4(Bruker)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'

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 0.1149(2) 0.77714(19) 0.69323(17) 0.0271(6) Uani d . . . 1 . .
N N1 0.1823(3) 0.7219(2) 0.62897(19) 0.0217(6) Uani d . . . 1 . .
C C2 0.3617(3) 0.7112(3) 0.5032(2) 0.0221(7) Uani d . . . 1 . .
H H2 0.429206 0.743529 0.462663 0.026000 Uiso calc U . R 1 . .
C C16 0.2401(3) 0.8872(3) 0.5403(2) 0.0226(7) Uani d . . . 1 . .
C C3 0.3299(3) 0.6077(3) 0.4871(2) 0.0230(7) Uani d . . . 1 . .
H H3 0.379944 0.567455 0.439902 0.028000 Uiso calc U . R 1 . .
C C4 0.2204(3) 0.5545(3) 0.5400(2) 0.0221(7) Uani d . . . 1 . .
C C9 0.1460(3) 0.6138(3) 0.6100(2) 0.0225(7) Uani d . . . 1 . .
C C1 0.2985(3) 0.7810(3) 0.5811(2) 0.0204(7) Uani d . . . 1 . .
C C5 0.1806(4) 0.4459(3) 0.5218(3) 0.0247(7) Uani d . . . 1 . .
C C15 0.5052(3) 0.8821(3) 0.6501(3) 0.0271(8) Uani d . . . 1 . .
H H15 0.491769 0.937264 0.602357 0.033000 Uiso calc U . R 1 . .
C C22 0.2525(4) 0.3818(3) 0.4509(3) 0.0280(8) Uani d . . . 1 . .
C C17 0.1990(3) 0.8925(3) 0.4432(3) 0.0276(8) Uani d . . . 1 . .
H H17 0.210434 0.830570 0.402425 0.033000 Uiso calc U . R 1 . .
C C10 0.4129(3) 0.7961(3) 0.6576(2) 0.0233(7) Uani d . . . 1 . .
C C6 0.0696(4) 0.4003(3) 0.5714(3) 0.0284(8) Uani d . . . 1 . .
H H6 0.042372 0.327447 0.557805 0.034000 Uiso calc U . R 1 . .
C C11 0.4345(4) 0.7165(3) 0.7281(2) 0.0265(8) Uani d . . . 1 . .
H H11 0.372499 0.657193 0.733370 0.032000 Uiso calc U . R 1 . .
C C18 0.1415(4) 0.9869(3) 0.4051(3) 0.0327(9) Uani d . . . 1 . .
H H18 0.113925 0.989173 0.338708 0.039000 Uiso calc U . R 1 . .
C C8 0.0366(4) 0.5672(3) 0.6609(3) 0.0274(8) Uani d . . . 1 . .
H H8 -0.011214 0.608018 0.708891 0.033000 Uiso calc U . R 1 . .
C C21 0.2211(4) 0.9791(3) 0.5990(3) 0.0289(8) Uani d . . . 1 . .
H H21 0.247167 0.976929 0.665656 0.035000 Uiso calc U . R 1 . .
C C14 0.6169(4) 0.8874(3) 0.7124(3) 0.0323(9) Uani d . . . 1 . .
H H14 0.680271 0.945710 0.706561 0.039000 Uiso calc U . R 1 . .
C C7 -0.0008(4) 0.4610(3) 0.6403(3) 0.0312(9) Uani d . . . 1 . .
H H7 -0.075836 0.429137 0.673782 0.037000 Uiso calc U . R 1 . .
C C13 0.6363(4) 0.8081(3) 0.7829(3) 0.0337(9) Uani d . . . 1 . .
H H13 0.712253 0.812483 0.825907 0.040000 Uiso calc U . R 1 . .
C C20 0.1645(4) 1.0732(3) 0.5607(3) 0.0350(9) Uani d . . . 1 . .
H H20 0.153131 1.135407 0.601201 0.042000 Uiso calc U . R 1 . .
C C12 0.5450(4) 0.7226(3) 0.7907(3) 0.0322(8) Uani d . . . 1 . .
H H12 0.558154 0.668013 0.838941 0.039000 Uiso calc U . R 1 . .
C C23 0.3116(4) 0.3266(3) 0.3925(3) 0.0324(8) Uani d . . . 1 . .
H H23 0.358539 0.282828 0.346216 0.039000 Uiso calc U . R 1 . .
C C19 0.1243(4) 1.0778(3) 0.4639(3) 0.0362(9) Uani d . . . 1 . .
H H19 0.085298 1.142620 0.438097 0.043000 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N1 . 1.293(3) ?
N1 C9 . 1.396(4) ?
N1 C1 . 1.500(4) ?
C2 C3 . 1.325(5) ?
C2 C1 . 1.502(4) ?
C2 H2 . 0.950000 ?
C16 C17 . 1.393(5) ?
C16 C21 . 1.397(5) ?
C16 C1 . 1.528(4) ?
C3 C4 . 1.449(5) ?
C3 H3 . 0.950000 ?
C4 C9 . 1.407(5) ?
C4 C5 . 1.409(5) ?
C9 C8 . 1.400(5) ?
C1 C10 . 1.546(5) ?
C5 C6 . 1.398(5) ?
C5 C22 . 1.435(5) ?
C15 C14 . 1.389(5) ?
C15 C10 . 1.392(5) ?
C15 H15 . 0.950000 ?
C22 C23 . 1.197(5) ?
C17 C18 . 1.389(5) ?
C17 H17 . 0.950000 ?
C10 C11 . 1.390(5) ?
C6 C7 . 1.387(5) ?
C6 H6 . 0.950000 ?
C11 C12 . 1.383(5) ?
C11 H11 . 0.950000 ?
C18 C19 . 1.385(6) ?
C18 H18 . 0.950000 ?
C8 C7 . 1.382(5) ?
C8 H8 . 0.950000 ?
C21 C20 . 1.383(5) ?
C21 H21 . 0.950000 ?
C14 C13 . 1.385(6) ?
C14 H14 . 0.950000 ?
C7 H7 . 0.950000 ?
C13 C12 . 1.381(6) ?
C13 H13 . 0.950000 ?
C20 C19 . 1.386(6) ?
C20 H20 . 0.950000 ?
C12 H12 . 0.950000 ?
C23 H23 . 0.950000 ?
C19 H19 . 0.950000 ?

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
O1 N1 C9 . . 119.6(3) ?
O1 N1 C1 . . 115.6(2) ?
C9 N1 C1 . . 124.7(3) ?
C3 C2 C1 . . 124.5(3) ?
C3 C2 H2 . . 117.700000 ?
C1 C2 H2 . . 117.700000 ?
C17 C16 C21 . . 118.3(3) ?
C17 C16 C1 . . 119.9(3) ?
C21 C16 C1 . . 121.7(3) ?
C2 C3 C4 . . 121.4(3) ?
C2 C3 H3 . . 119.300000 ?
C4 C3 H3 . . 119.300000 ?
C9 C4 C5 . . 117.8(3) ?
C9 C4 C3 . . 119.4(3) ?
C5 C4 C3 . . 122.7(3) ?
N1 C9 C8 . . 119.3(3) ?
N1 C9 C4 . . 119.1(3) ?
C8 C9 C4 . . 121.6(3) ?
N1 C1 C2 . . 110.4(3) ?
N1 C1 C16 . . 106.8(2) ?
C2 C1 C16 . . 112.3(3) ?
N1 C1 C10 . . 108.0(2) ?
C2 C1 C10 . . 104.7(3) ?
C16 C1 C10 . . 114.6(3) ?
C6 C5 C4 . . 120.4(3) ?
C6 C5 C22 . . 119.4(3) ?
C4 C5 C22 . . 120.1(3) ?
C14 C15 C10 . . 120.0(3) ?
C14 C15 H15 . . 120.000000 ?
C10 C15 H15 . . 120.000000 ?
C23 C22 C5 . . 178.8(4) ?
C18 C17 C16 . . 121.1(3) ?
C18 C17 H17 . . 119.500000 ?
C16 C17 H17 . . 119.500000 ?
C11 C10 C15 . . 118.9(3) ?
C11 C10 C1 . . 119.9(3) ?
C15 C10 C1 . . 120.7(3) ?
C7 C6 C5 . . 120.2(3) ?
C7 C6 H6 . . 119.900000 ?
C5 C6 H6 . . 119.900000 ?
C12 C11 C10 . . 120.9(3) ?
C12 C11 H11 . . 119.600000 ?
C10 C11 H11 . . 119.600000 ?
C19 C18 C17 . . 120.0(3) ?
C19 C18 H18 . . 120.000000 ?
C17 C18 H18 . . 120.000000 ?
C7 C8 C9 . . 119.0(3) ?
C7 C8 H8 . . 120.500000 ?
C9 C8 H8 . . 120.500000 ?
C20 C21 C16 . . 120.5(4) ?
C20 C21 H21 . . 119.800000 ?
C16 C21 H21 . . 119.800000 ?
C13 C14 C15 . . 120.4(4) ?
C13 C14 H14 . . 119.800000 ?
C15 C14 H14 . . 119.800000 ?
C8 C7 C6 . . 120.9(3) ?
C8 C7 H7 . . 119.600000 ?
C6 C7 H7 . . 119.500000 ?
C12 C13 C14 . . 119.8(3) ?
C12 C13 H13 . . 120.100000 ?
C14 C13 H13 . . 120.100000 ?
C21 C20 C19 . . 120.7(4) ?
C21 C20 H20 . . 119.600000 ?
C19 C20 H20 . . 119.600000 ?
C13 C12 C11 . . 119.9(4) ?
C13 C12 H12 . . 120.000000 ?
C11 C12 H12 . . 120.000000 ?
C22 C23 H23 . . 180.000000 ?
C18 C19 C20 . . 119.4(3) ?
C18 C19 H19 . . 120.300000 ?
C20 C19 H19 . . 120.300000 ?

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
C1 C2 C3 C4 . . . . 5.1(5) ?
C2 C3 C4 C9 . . . . 0.0(5) ?
C2 C3 C4 C5 . . . . 177.4(3) ?
O1 N1 C9 C8 . . . . 0.2(4) ?
C1 N1 C9 C8 . . . . 178.9(3) ?
O1 N1 C9 C4 . . . . -179.9(3) ?
C1 N1 C9 C4 . . . . -1.2(5) ?
C5 C4 C9 N1 . . . . -179.4(3) ?
C3 C4 C9 N1 . . . . -1.9(4) ?
C5 C4 C9 C8 . . . . 0.5(5) ?
C3 C4 C9 C8 . . . . 178.0(3) ?
O1 N1 C1 C2 . . . . -175.9(2) ?
C9 N1 C1 C2 . . . . 5.3(4) ?
O1 N1 C1 C16 . . . . -53.6(3) ?
C9 N1 C1 C16 . . . . 127.7(3) ?
O1 N1 C1 C10 . . . . 70.2(3) ?
C9 N1 C1 C10 . . . . -108.5(3) ?
C3 C2 C1 N1 . . . . -7.4(4) ?
C3 C2 C1 C16 . . . . -126.4(3) ?
C3 C2 C1 C10 . . . . 108.6(4) ?
C17 C16 C1 N1 . . . . -95.4(3) ?
C21 C16 C1 N1 . . . . 81.8(4) ?
C17 C16 C1 C2 . . . . 25.7(4) ?
C21 C16 C1 C2 . . . . -157.0(3) ?
C17 C16 C1 C10 . . . . 145.0(3) ?
C21 C16 C1 C10 . . . . -37.8(4) ?
C9 C4 C5 C6 . . . . 0.8(5) ?
C3 C4 C5 C6 . . . . -176.6(3) ?
C9 C4 C5 C22 . . . . 179.7(3) ?
C3 C4 C5 C22 . . . . 2.3(5) ?
C21 C16 C17 C18 . . . . 0.6(5) ?
C1 C16 C17 C18 . . . . 177.9(3) ?
C14 C15 C10 C11 . . . . 0.1(5) ?
C14 C15 C10 C1 . . . . -172.3(3) ?
N1 C1 C10 C11 . . . . 34.1(4) ?
C2 C1 C10 C11 . . . . -83.6(3) ?
C16 C1 C10 C11 . . . . 153.0(3) ?
N1 C1 C10 C15 . . . . -153.6(3) ?
C2 C1 C10 C15 . . . . 88.8(4) ?
C16 C1 C10 C15 . . . . -34.7(4) ?
C4 C5 C6 C7 . . . . -1.2(5) ?
C22 C5 C6 C7 . . . . 179.8(3) ?
C15 C10 C11 C12 . . . . 0.6(5) ?
C1 C10 C11 C12 . . . . 173.1(3) ?
C16 C17 C18 C19 . . . . 0.0(6) ?
N1 C9 C8 C7 . . . . 178.6(3) ?
C4 C9 C8 C7 . . . . -1.4(5) ?
C17 C16 C21 C20 . . . . -0.9(5) ?
C1 C16 C21 C20 . . . . -178.2(3) ?
C10 C15 C14 C13 . . . . -0.8(5) ?
C9 C8 C7 C6 . . . . 1.0(5) ?
C5 C6 C7 C8 . . . . 0.3(5) ?
C15 C14 C13 C12 . . . . 0.8(5) ?
C16 C21 C20 C19 . . . . 0.7(6) ?
C14 C13 C12 C11 . . . . -0.1(5) ?
C10 C11 C12 C13 . . . . -0.6(5) ?
C17 C18 C19 C20 . . . . -0.2(6) ?
C21 C20 C19 C18 . . . . -0.2(6) ?


# start Validation Reply Form
_vrf_STRVA01_X240718TM_5EDPQN_lt 
;
PROBLEM: Flack parameter is too small
RESPONSE: The absolute structure was determined using
a separate dataset with Cu radiation.
;
_vrf_PLAT031_X240718TM_5EDPQN_lt 
;
PROBLEM: Refined Extinction Parameter Within Range of ...      2.500 Sigma 
RESPONSE: The small value indicates that extinction effects are minor
but the parameter is retained for the best model fit.
;
_vrf_PLAT340_X240718TM_5EDPQN_lt 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00508 Ang.  
RESPONSE: The bond precision is slightly lower than the limit 
due to the thermal motion of the ethynyl group, but it is acceptable 
given the overall data quality.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_X251125TM_5EDPQN_cu_lt
_database_code_depnum_ccdc_archive 'CCDC 2484892'
loop_
_audit_author_name
_audit_author_address
'Masaomi Takii'
;Keio University
Japan
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_audit_creation_method           'APEX4 v2021.10-0'
_chemical_name_systematic        
'5-ethynyl-2,2-diphenyl-1,2-dihydroquinoline N-oxyl'
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H16 N O'
_chemical_formula_sum            'C23 H16 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         322.37
_chemical_absolute_configuration unk

_chemical_melting_point          404

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.24980(10)
_cell_length_b                   13.7016(2)
_cell_length_c                   9.78620(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1642.53(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      5.5553
_cell_measurement_theta_max      66.3777
_cell_measurement_temperature    90.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'dark black-red'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676

_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.(2)

_diffrn_source                   'micro focus sealed tube'
_diffrn_source_type              'INCOATEC I\mS'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            12516
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_theta_min         5.55
_diffrn_reflns_theta_max         66.37
_diffrn_reflns_theta_full        66.37
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8

_refine_special_details          
;
;

_reflns_number_total             2873
_reflns_number_gt                2734
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.988

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0807
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.2216P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0053(8)
_refine_ls_abs_structure_details 
;

Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)

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'

_computing_data_collection       APEX4(Bruker)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'

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 0.22298(11) 0.30695(10) 0.11483(12) 0.0221(3) Uani d . . . 1 . .
N N1 0.27780(13) 0.37069(11) 0.18200(14) 0.0177(3) Uani d . . . 1 . .
C C16 0.11235(15) 0.46009(15) 0.24010(16) 0.0192(4) Uani d . . . 1 . .
C C2 0.28860(16) 0.49701(13) 0.36236(17) 0.0189(4) Uani d . . . 1 . .
H H2 0.256163 0.537321 0.430102 0.023000 Uiso calc U . R 1 . .
C C3 0.39277(16) 0.51346(14) 0.33034(18) 0.0194(4) Uani d . . . 1 . .
H H3 0.433062 0.560869 0.380083 0.023000 Uiso calc U . R 1 . .
C C22 0.61854(15) 0.54889(16) 0.25295(19) 0.0240(4) Uani d . . . 1 . .
C C15 0.11791(16) 0.35041(15) 0.50560(18) 0.0225(4) Uani d . . . 1 . .
H H15 0.063493 0.398961 0.492880 0.027000 Uiso calc U . R 1 . .
C C14 0.11211(18) 0.28724(16) 0.61740(18) 0.0276(4) Uani d . . . 1 . .
H H14 0.053270 0.292507 0.680202 0.033000 Uiso calc U . R 1 . .
C C9 0.38592(15) 0.39038(14) 0.14602(17) 0.0194(4) Uani d . . . 1 . .
C C5 0.55432(16) 0.47858(15) 0.18064(19) 0.0218(4) Uani d . . . 1 . .
C C18 0.01260(18) 0.59494(16) 0.14089(19) 0.0278(4) Uani d . . . 1 . .
H H18 0.010022 0.661291 0.112889 0.033000 Uiso calc U . R 1 . .
C C4 0.44560(16) 0.46000(15) 0.22053(17) 0.0189(4) Uani d . . . 1 . .
C C10 0.20355(15) 0.34210(14) 0.41290(17) 0.0188(4) Uani d . . . 1 . .
C C1 0.21892(14) 0.41891(13) 0.29845(16) 0.0173(4) Uani d . . . 1 . .
C C17 0.10788(16) 0.55725(15) 0.19879(18) 0.0231(4) Uani d . . . 1 . .
H H17 0.169921 0.598074 0.210039 0.028000 Uiso calc U . R 1 . .
C C6 0.59994(15) 0.42871(17) 0.06896(19) 0.0260(4) Uani d . . . 1 . .
H H6 0.672694 0.442460 0.041392 0.031000 Uiso calc U . R 1 . .
C C8 0.43243(16) 0.33913(15) 0.03624(19) 0.0232(4) Uani d . . . 1 . .
H H8 0.391422 0.291252 -0.011668 0.028000 Uiso calc U . R 1 . .
C C21 0.02070(16) 0.40046(16) 0.22105(17) 0.0238(4) Uani d . . . 1 . .
H H21 0.023113 0.333737 0.247293 0.029000 Uiso calc U . R 1 . .
C C11 0.28353(17) 0.27219(15) 0.43419(18) 0.0225(4) Uani d . . . 1 . .
H H11 0.342922 0.267341 0.372129 0.027000 Uiso calc U . R 1 . .
C C13 0.19174(19) 0.21705(15) 0.63696(19) 0.0295(5) Uani d . . . 1 . .
H H13 0.187456 0.174270 0.713173 0.035000 Uiso calc U . R 1 . .
C C23 0.67359(16) 0.60770(16) 0.3118(2) 0.0279(4) Uani d . . . 1 . .
H H23 0.717226 0.654314 0.358527 0.033000 Uiso calc U . R 1 . .
C C7 0.53937(17) 0.35962(17) -0.00111(18) 0.0274(4) Uani d . . . 1 . .
H H7 0.571402 0.325765 -0.075742 0.033000 Uiso calc U . R 1 . .
C C19 -0.07795(16) 0.53596(19) 0.1242(2) 0.0306(5) Uani d . . . 1 . .
H H19 -0.142997 0.561834 0.085711 0.037000 Uiso calc U . R 1 . .
C C12 0.27794(18) 0.20894(15) 0.54546(19) 0.0274(4) Uani d . . . 1 . .
H H12 0.332628 0.160689 0.558635 0.033000 Uiso calc U . R 1 . .
C C20 -0.07354(16) 0.43886(18) 0.1639(2) 0.0299(5) Uani d . . . 1 . .
H H20 -0.135675 0.398279 0.151759 0.036000 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N1 . 1.283(2) ?
N1 C9 . 1.397(2) ?
N1 C1 . 1.502(2) ?
C16 C17 . 1.392(3) ?
C16 C21 . 1.401(3) ?
C16 C1 . 1.533(2) ?
C2 C3 . 1.333(3) ?
C2 C1 . 1.505(2) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.453(3) ?
C3 H3 . 0.950000 ?
C22 C23 . 1.198(3) ?
C22 C5 . 1.431(3) ?
C15 C10 . 1.391(3) ?
C15 C14 . 1.397(3) ?
C15 H15 . 0.950000 ?
C14 C13 . 1.383(3) ?
C14 H14 . 0.950000 ?
C9 C8 . 1.404(3) ?
C9 C4 . 1.406(3) ?
C5 C6 . 1.405(3) ?
C5 C4 . 1.411(3) ?
C18 C19 . 1.382(3) ?
C18 C17 . 1.396(3) ?
C18 H18 . 0.950000 ?
C10 C11 . 1.386(3) ?
C10 C1 . 1.548(2) ?
C17 H17 . 0.950000 ?
C6 C7 . 1.385(3) ?
C6 H6 . 0.950000 ?
C8 C7 . 1.389(3) ?
C8 H8 . 0.950000 ?
C21 C20 . 1.387(3) ?
C21 H21 . 0.950000 ?
C11 C12 . 1.393(3) ?
C11 H11 . 0.950000 ?
C13 C12 . 1.389(3) ?
C13 H13 . 0.950000 ?
C23 H23 . 0.950000 ?
C7 H7 . 0.950000 ?
C19 C20 . 1.387(3) ?
C19 H19 . 0.950000 ?
C12 H12 . 0.950000 ?
C20 H20 . 0.950000 ?

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
O1 N1 C9 . . 119.91(14) ?
O1 N1 C1 . . 115.91(14) ?
C9 N1 C1 . . 124.17(15) ?
C17 C16 C21 . . 119.17(18) ?
C17 C16 C1 . . 119.58(17) ?
C21 C16 C1 . . 121.17(18) ?
C3 C2 C1 . . 124.43(17) ?
C3 C2 H2 . . 117.800000 ?
C1 C2 H2 . . 117.800000 ?
C2 C3 C4 . . 121.00(17) ?
C2 C3 H3 . . 119.500000 ?
C4 C3 H3 . . 119.500000 ?
C23 C22 C5 . . 178.9(2) ?
C10 C15 C14 . . 119.89(19) ?
C10 C15 H15 . . 120.100000 ?
C14 C15 H15 . . 120.100000 ?
C13 C14 C15 . . 120.22(19) ?
C13 C14 H14 . . 119.900000 ?
C15 C14 H14 . . 119.900000 ?
N1 C9 C8 . . 118.75(18) ?
N1 C9 C4 . . 119.57(16) ?
C8 C9 C4 . . 121.69(17) ?
C6 C5 C4 . . 120.20(19) ?
C6 C5 C22 . . 119.57(18) ?
C4 C5 C22 . . 120.23(17) ?
C19 C18 C17 . . 120.2(2) ?
C19 C18 H18 . . 119.900000 ?
C17 C18 H18 . . 119.900000 ?
C9 C4 C5 . . 118.02(17) ?
C9 C4 C3 . . 119.62(17) ?
C5 C4 C3 . . 122.29(18) ?
C11 C10 C15 . . 119.44(17) ?
C11 C10 C1 . . 119.50(16) ?
C15 C10 C1 . . 120.51(17) ?
N1 C1 C2 . . 110.84(14) ?
N1 C1 C16 . . 106.76(13) ?
C2 C1 C16 . . 112.10(15) ?
N1 C1 C10 . . 107.96(14) ?
C2 C1 C10 . . 104.58(13) ?
C16 C1 C10 . . 114.59(15) ?
C16 C17 C18 . . 120.3(2) ?
C16 C17 H17 . . 119.900000 ?
C18 C17 H17 . . 119.900000 ?
C7 C6 C5 . . 120.31(18) ?
C7 C6 H6 . . 119.800000 ?
C5 C6 H6 . . 119.800000 ?
C7 C8 C9 . . 118.88(19) ?
C7 C8 H8 . . 120.600000 ?
C9 C8 H8 . . 120.600000 ?
C20 C21 C16 . . 120.0(2) ?
C20 C21 H21 . . 120.000000 ?
C16 C21 H21 . . 120.000000 ?
C10 C11 C12 . . 120.83(18) ?
C10 C11 H11 . . 119.600000 ?
C12 C11 H11 . . 119.600000 ?
C14 C13 C12 . . 120.16(18) ?
C14 C13 H13 . . 119.900000 ?
C12 C13 H13 . . 119.900000 ?
C22 C23 H23 . . 180.000000 ?
C6 C7 C8 . . 120.89(18) ?
C6 C7 H7 . . 119.600000 ?
C8 C7 H7 . . 119.600000 ?
C18 C19 C20 . . 119.77(18) ?
C18 C19 H19 . . 120.100000 ?
C20 C19 H19 . . 120.100000 ?
C13 C12 C11 . . 119.4(2) ?
C13 C12 H12 . . 120.300000 ?
C11 C12 H12 . . 120.300000 ?
C21 C20 C19 . . 120.6(2) ?
C21 C20 H20 . . 119.700000 ?
C19 C20 H20 . . 119.700000 ?

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
C1 C2 C3 C4 . . . . 4.8(3) ?
C10 C15 C14 C13 . . . . 0.6(3) ?
O1 N1 C9 C8 . . . . -0.2(2) ?
C1 N1 C9 C8 . . . . 178.93(15) ?
O1 N1 C9 C4 . . . . -179.71(15) ?
C1 N1 C9 C4 . . . . -0.6(2) ?
N1 C9 C4 C5 . . . . -179.51(15) ?
C8 C9 C4 C5 . . . . 1.0(3) ?
N1 C9 C4 C3 . . . . -2.5(2) ?
C8 C9 C4 C3 . . . . 177.95(17) ?
C6 C5 C4 C9 . . . . 0.4(3) ?
C22 C5 C4 C9 . . . . 179.89(16) ?
C6 C5 C4 C3 . . . . -176.50(17) ?
C22 C5 C4 C3 . . . . 3.0(3) ?
C2 C3 C4 C9 . . . . 0.5(3) ?
C2 C3 C4 C5 . . . . 177.36(17) ?
C14 C15 C10 C11 . . . . -1.3(3) ?
C14 C15 C10 C1 . . . . -172.71(16) ?
O1 N1 C1 C2 . . . . -175.85(14) ?
C9 N1 C1 C2 . . . . 5.0(2) ?
O1 N1 C1 C16 . . . . -53.51(19) ?
C9 N1 C1 C16 . . . . 127.36(17) ?
O1 N1 C1 C10 . . . . 70.16(18) ?
C9 N1 C1 C10 . . . . -108.97(18) ?
C3 C2 C1 N1 . . . . -7.2(2) ?
C3 C2 C1 C16 . . . . -126.34(18) ?
C3 C2 C1 C10 . . . . 108.94(19) ?
C17 C16 C1 N1 . . . . -95.30(18) ?
C21 C16 C1 N1 . . . . 81.44(19) ?
C17 C16 C1 C2 . . . . 26.3(2) ?
C21 C16 C1 C2 . . . . -157.00(16) ?
C17 C16 C1 C10 . . . . 145.24(16) ?
C21 C16 C1 C10 . . . . -38.0(2) ?
C11 C10 C1 N1 . . . . 34.6(2) ?
C15 C10 C1 N1 . . . . -153.93(16) ?
C11 C10 C1 C2 . . . . -83.46(19) ?
C15 C10 C1 C2 . . . . 88.0(2) ?
C11 C10 C1 C16 . . . . 153.42(16) ?
C15 C10 C1 C16 . . . . -35.1(2) ?
C21 C16 C17 C18 . . . . 0.9(3) ?
C1 C16 C17 C18 . . . . 177.70(16) ?
C19 C18 C17 C16 . . . . 0.0(3) ?
C4 C5 C6 C7 . . . . -1.3(3) ?
C22 C5 C6 C7 . . . . 179.23(17) ?
N1 C9 C8 C7 . . . . 179.02(17) ?
C4 C9 C8 C7 . . . . -1.4(3) ?
C17 C16 C21 C20 . . . . -1.1(3) ?
C1 C16 C21 C20 . . . . -177.87(16) ?
C15 C10 C11 C12 . . . . 1.4(3) ?
C1 C10 C11 C12 . . . . 172.91(17) ?
C15 C14 C13 C12 . . . . 0.0(3) ?
C5 C6 C7 C8 . . . . 0.8(3) ?
C9 C8 C7 C6 . . . . 0.5(3) ?
C17 C18 C19 C20 . . . . -0.7(3) ?
C14 C13 C12 C11 . . . . 0.1(3) ?
C10 C11 C12 C13 . . . . -0.8(3) ?
C16 C21 C20 C19 . . . . 0.5(3) ?
C18 C19 C20 C21 . . . . 0.4(3) ?


# start Validation Reply Form
_vrf_PLAT911_X251125TM_5EDPQN_cu_lt 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.594         15 Report
RESPONSE: The missing reflections are obscured by the beamstop or were omitted
as outliers.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_preparation       'Magnetic properties'
