# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2414708'
loop_
_audit_author_name
_audit_author_address
'Tao Cao'
;Nanjing University of Chinese Medicine
China
;
_audit_update_record             
;
2025-01-06 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;
_audit_creation_date             2024-08-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 D2 N O4'
_chemical_formula_sum            'C20 H19 D2 N O4'
_chemical_formula_weight         341.39
_chemical_melting_point          ?
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'
D D 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.8735(11)
_cell_length_b                   17.634(3)
_cell_length_c                   17.716(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.820(6)
_cell_angle_gamma                90
_cell_volume                     1825.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3679
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.37
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0621 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.8855.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15947
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_min         2.583
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1949
_reflns_number_total             3156
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.037
_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)+(0.0524P)²+0.6544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1369
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C11(H11A,H11B,H11C)
2.b Ternary CH refined with riding coordinates:
 C7(D7), C8(D8)
2.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), N1(H1A)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9922(5) 0.12645(15) 0.60299(15) 0.0573(7) Uani 1 1 d . . . . .
H1 H 1.1169 0.1257 0.5746 0.069 Uiso 1 1 calc R U . . .
C2 C 0.9721(5) 0.07041(15) 0.65657(16) 0.0663(8) Uani 1 1 d . . . . .
H2 H 1.0813 0.0322 0.6633 0.080 Uiso 1 1 calc R U . . .
C3 C 0.7920(6) 0.07120(16) 0.69951(16) 0.0680(8) Uani 1 1 d . . . . .
H3 H 0.7799 0.0343 0.7364 0.082 Uiso 1 1 calc R U . . .
C4 C 0.6289(6) 0.12680(18) 0.68799(18) 0.0750(9) Uani 1 1 d . . . . .
H4 H 0.5049 0.1271 0.7167 0.090 Uiso 1 1 calc R U . . .
C5 C 0.6474(5) 0.18263(16) 0.63384(16) 0.0640(8) Uani 1 1 d . . . . .
H5 H 0.5351 0.2198 0.6264 0.077 Uiso 1 1 calc R U . . .
C6 C 0.8314(4) 0.18354(13) 0.59071(13) 0.0459(6) Uani 1 1 d . . . . .
C7 C 0.8631(4) 0.24443(13) 0.53411(13) 0.0448(6) Uani 1 1 d . . . . .
D7 D 1.0059 0.2730 0.5448 0.054 Uiso 1 1 calc R U . . .
C8 C 0.6749(4) 0.28915(13) 0.49430(13) 0.0446(6) Uani 1 1 d . . . . .
D8 D 0.5224 0.2735 0.5061 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7955(4) 0.23049(12) 0.44899(13) 0.0403(6) Uani 1 1 d . . . . .
C10 C 0.6862(4) 0.15530(14) 0.42826(14) 0.0470(6) Uani 1 1 d . . . . .
C11 C 0.3530(5) 0.08202(17) 0.4168(2) 0.1013(13) Uani 1 1 d . . . . .
H11A H 0.3948 0.0638 0.3690 0.152 Uiso 1 1 d R U . . .
H11B H 0.1900 0.0885 0.4137 0.152 Uiso 1 1 d R U . . .
H11C H 0.4004 0.0460 0.4559 0.152 Uiso 1 1 d R U . . .
C12 C 0.9615(4) 0.25870(14) 0.39751(15) 0.0462(6) Uani 1 1 d . . . . .
C13 C 1.0882(6) 0.2505(2) 0.27611(18) 0.0923(11) Uani 1 1 d . . . . .
H13A H 1.0531 0.2241 0.2290 0.138 Uiso 1 1 calc R U . . .
H13B H 1.2400 0.2375 0.2973 0.138 Uiso 1 1 calc R U . . .
H13C H 1.0791 0.3042 0.2673 0.138 Uiso 1 1 calc R U . . .
C14 C 0.6959(4) 0.37292(13) 0.48038(14) 0.0483(6) Uani 1 1 d . . . . .
H14A H 0.6568 0.4009 0.5244 0.058 Uiso 1 1 calc R U . . .
H14B H 0.8525 0.3851 0.4722 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5376(4) 0.46688(13) 0.38530(13) 0.0434(6) Uani 1 1 d . . . . .
C16 C 0.7151(5) 0.51850(14) 0.39911(15) 0.0564(7) Uani 1 1 d . . . . .
H16 H 0.8422 0.5061 0.4324 0.068 Uiso 1 1 calc R U . . .
C17 C 0.7037(6) 0.58850(16) 0.36347(18) 0.0706(9) Uani 1 1 d . . . . .
H17 H 0.8248 0.6223 0.3728 0.085 Uiso 1 1 calc R U . . .
C18 C 0.5177(6) 0.60881(16) 0.31484(17) 0.0722(9) Uani 1 1 d . . . . .
H18 H 0.5121 0.6559 0.2912 0.087 Uiso 1 1 calc R U . . .
C19 C 0.3397(5) 0.55862(16) 0.30152(16) 0.0661(8) Uani 1 1 d . . . . .
H19 H 0.2126 0.5718 0.2685 0.079 Uiso 1 1 calc R U . . .
C20 C 0.3475(4) 0.48916(15) 0.33645(15) 0.0548(7) Uani 1 1 d . . . . .
H20 H 0.2241 0.4562 0.3275 0.066 Uiso 1 1 calc R U . . .
N1 N 0.5447(3) 0.39449(11) 0.41482(12) 0.0516(6) Uani 1 1 d . . . . .
H1A H 0.4548 0.3607 0.3931 0.062 Uiso 1 1 calc R U . . .
O1 O 0.7888(3) 0.10131(11) 0.41008(13) 0.0796(7) Uani 1 1 d . . . . .
O2 O 0.4652(3) 0.15478(10) 0.43443(12) 0.0706(6) Uani 1 1 d . . . . .
O3 O 0.9258(3) 0.22906(10) 0.32845(10) 0.0670(6) Uani 1 1 d . . . . .
O4 O 1.1103(3) 0.30384(11) 0.41563(11) 0.0652(5) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.384(4) . ?
C1 C6 1.383(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 C7 1.494(3) . ?
C7 D7 0.9800 . ?
C7 C8 1.478(3) . ?
C7 C9 1.540(3) . ?
C8 D8 0.9800 . ?
C8 C9 1.527(3) . ?
C8 C14 1.505(3) . ?
C9 C10 1.502(3) . ?
C9 C12 1.487(3) . ?
C10 O1 1.189(3) . ?
C10 O2 1.314(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 O2 1.462(3) . ?
C12 O3 1.327(3) . ?
C12 O4 1.202(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 O3 1.446(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 N1 1.440(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.398(3) . ?
C15 N1 1.379(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(4) . ?
C20 H20 0.9300 . ?
N1 H1A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C6 C1 C2 121.6(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.6(2) . . ?
C1 C6 C7 120.0(2) . . ?
C5 C6 C7 122.4(2) . . ?
C6 C7 D7 113.7 . . ?
C6 C7 C9 120.35(19) . . ?
C8 C7 C6 124.5(2) . . ?
C8 C7 D7 113.7 . . ?
C8 C7 C9 60.76(15) . . ?
C9 C7 D7 113.7 . . ?
C7 C8 D8 113.8 . . ?
C7 C8 C9 61.63(15) . . ?
C7 C8 C14 122.2(2) . . ?
C9 C8 D8 113.8 . . ?
C14 C8 D8 113.8 . . ?
C14 C8 C9 121.9(2) . . ?
C8 C9 C7 57.61(14) . . ?
C10 C9 C7 116.21(19) . . ?
C10 C9 C8 121.1(2) . . ?
C12 C9 C7 115.29(19) . . ?
C12 C9 C8 117.63(19) . . ?
C12 C9 C10 115.8(2) . . ?
O1 C10 C9 123.9(2) . . ?
O1 C10 O2 123.3(2) . . ?
O2 C10 C9 112.8(2) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.4 . . ?
O2 C11 H11C 109.5 . . ?
O3 C12 C9 112.4(2) . . ?
O4 C12 C9 124.2(2) . . ?
O4 C12 O3 123.3(2) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
C8 C14 H14A 109.7 . . ?
C8 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
N1 C14 C8 109.72(19) . . ?
N1 C14 H14A 109.7 . . ?
N1 C14 H14B 109.7 . . ?
C16 C15 C20 117.6(2) . . ?
N1 C15 C16 123.2(2) . . ?
N1 C15 C20 119.1(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.2(3) . . ?
C19 C20 H20 119.4 . . ?
C14 N1 H1A 118.6 . . ?
C15 N1 C14 122.88(19) . . ?
C15 N1 H1A 118.6 . . ?
C10 O2 C11 114.6(2) . . ?
C12 O3 C13 115.8(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.5(4) . . . . ?
C1 C6 C7 C8 155.0(2) . . . . ?
C1 C6 C7 C9 81.5(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C6 C7 178.0(2) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C4 C5 C6 C7 -177.4(2) . . . . ?
C5 C6 C7 C8 -26.7(4) . . . . ?
C5 C6 C7 C9 -100.2(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C6 C7 C8 C9 -108.6(2) . . . . ?
C6 C7 C8 C14 139.7(2) . . . . ?
C6 C7 C9 C8 115.1(2) . . . . ?
C6 C7 C9 C10 3.3(3) . . . . ?
C6 C7 C9 C12 -137.0(2) . . . . ?
C7 C8 C9 C10 103.2(2) . . . . ?
C7 C8 C9 C12 -103.8(2) . . . . ?
C7 C8 C14 N1 154.1(2) . . . . ?
C7 C9 C10 O1 -94.6(3) . . . . ?
C7 C9 C10 O2 83.6(3) . . . . ?
C7 C9 C12 O3 164.03(19) . . . . ?
C7 C9 C12 O4 -16.7(3) . . . . ?
C8 C7 C9 C10 -111.7(2) . . . . ?
C8 C7 C9 C12 107.9(2) . . . . ?
C8 C9 C10 O1 -161.0(3) . . . . ?
C8 C9 C10 O2 17.2(3) . . . . ?
C8 C9 C12 O3 -130.9(2) . . . . ?
C8 C9 C12 O4 48.4(3) . . . . ?
C8 C14 N1 C15 -175.6(2) . . . . ?
C9 C7 C8 C14 -111.7(2) . . . . ?
C9 C8 C14 N1 79.7(3) . . . . ?
C9 C10 O2 C11 -178.4(2) . . . . ?
C9 C12 O3 C13 -176.7(2) . . . . ?
C10 C9 C12 O3 23.5(3) . . . . ?
C10 C9 C12 O4 -157.2(2) . . . . ?
C12 C9 C10 O1 45.5(3) . . . . ?
C12 C9 C10 O2 -136.3(2) . . . . ?
C14 C8 C9 C7 112.1(2) . . . . ?
C14 C8 C9 C10 -144.7(2) . . . . ?
C14 C8 C9 C12 8.3(3) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C16 C15 C20 C19 2.0(4) . . . . ?
C16 C15 N1 C14 20.6(4) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C15 -1.2(4) . . . . ?
C20 C15 C16 C17 -1.8(4) . . . . ?
C20 C15 N1 C14 -162.1(2) . . . . ?
N1 C15 C16 C17 175.5(2) . . . . ?
N1 C15 C20 C19 -175.4(2) . . . . ?
O1 C10 O2 C11 -0.2(4) . . . . ?
O4 C12 O3 C13 4.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
