# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_20230321-ch-1
_database_code_depnum_ccdc_archive 'CCDC 2293953'
loop_
_audit_author_name
_audit_author_address
'cao hui'
;hubei university
China
;
_audit_update_record             
;
2023-10-17 deposited with the CCDC.	2024-03-07 downloaded from the CCDC.
;
_audit_creation_date             2023-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ch
_chemical_formula_moiety         'C13 H17 N O4 Se'
_chemical_formula_sum            'C13 H17 N O4 Se'
_chemical_formula_weight         330.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Se'
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'
Se Se -0.7943 1.1372 '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                   12.5578(3)
_cell_length_b                   12.4264(3)
_cell_length_c                   9.7765(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.148(2)
_cell_angle_gamma                90
_cell_volume                     1472.60(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6767
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2860
_cell_measurement_theta_min      5.8570
_shelx_estimated_absorpt_T_max   0.675
_shelx_estimated_absorpt_T_min   0.636
_exptl_absorpt_coefficient_mu    3.550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11310
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.573
_diffrn_reflns_theta_min         3.646
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -77.00   0.50    0.75    --  -47.95-127.00 -83.00   82
  2  ω    -96.00 -71.00   0.50    0.75    --  -47.95-143.00 106.00   50
  3  ω     46.00  84.00   0.50    0.75    --   47.95-127.00 -83.00   76
  4  ω     51.00  76.00   0.50    0.75    --   47.95-143.00 106.00   50
  5  ω   -108.00 -83.00   0.50    2.99    --  -86.25-143.00 106.00   50
  6  ω   -159.00 -79.00   0.50    2.99    --  -86.25-127.00 -83.00  160
  7  ω     39.00 102.00   0.50    2.99    --  106.49-127.00 -83.00  126
  8  ω    112.00 137.00   0.50    2.99    --  106.49 127.00  -7.00   50
  9  ω     94.00 125.00   0.50    2.99    --  106.49-143.00 106.00   62
 10  ω     65.00  91.00   0.50    2.99    --  106.49-143.00 106.00   52
 11  ω    -26.00  27.00   0.50    0.75    --  -47.95  19.00 -60.00  106
 12  ω    -23.00  26.00   0.50    0.75    --  -47.95  19.00-150.00   98
 13  ω    -78.00 -53.00   0.50    0.75    --  -47.95 127.00  -7.00   50
 14  ω   -114.00 -73.00   0.50    0.75    --  -47.95-125.00  30.00   82
 15  ω   -161.00 -73.00   0.50    2.99    --  -86.25 -15.00  90.00  176
 16  ω    -50.00 -15.00   0.50    2.99    --  -86.25  45.00-180.00   70
 17  ω    -50.00 -18.00   0.50    2.99    --  -86.25  45.00-150.00   64
 18  ω     36.00  71.00   0.50    2.99    --  106.49 -61.00 -30.00   70
 19  ω     37.00  78.00   0.50    2.99    --  106.49-125.00 -30.00   82
 20  ω     38.00  95.00   0.50    2.99    --  106.49 -94.00 -90.00  114
 21  ω     38.00  63.00   0.50    2.99    --  106.49 -61.00 120.00   50
 22  ω     82.00 109.00   0.50    2.99    --  106.49-125.00 -30.00   54
 23  ω     34.00  67.00   0.50    2.99    --  106.49 -61.00  90.00   66
 24  ω    147.00 173.00   0.50    2.99    --  106.49 125.00-150.00   52
 25  ω     78.00 103.00   0.50    2.99    --  106.49 -94.00  90.00   50
 26  ω     96.00 134.00   0.50    2.99    --  106.49 125.00-150.00   76
 27  ω     35.00  61.00   0.50    2.99    --  106.49 -94.00  90.00   52
 28  ω    104.00 166.00   0.50    2.99    --  106.49  61.00  30.00  124
 29  ω     37.00  62.00   0.50    2.99    --  106.49 -61.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0908859000
_diffrn_orient_matrix_UB_12      0.0865753000
_diffrn_orient_matrix_UB_13      0.0273559000
_diffrn_orient_matrix_UB_21      0.0886747000
_diffrn_orient_matrix_UB_22      -0.0884565000
_diffrn_orient_matrix_UB_23      0.0397528000
_diffrn_orient_matrix_UB_31      0.0038505000
_diffrn_orient_matrix_UB_32      -0.0073180000
_diffrn_orient_matrix_UB_33      -0.1559899000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2466
_reflns_number_total             2939
_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       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.5487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0868
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C3(H3), C2(H2), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_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
Se1 Se 0.38819(2) 0.72855(3) 0.91157(3) 0.05501(12) Uani 1 1 d . . . . .
O1 O 0.14240(13) 0.77759(11) 0.88728(14) 0.0357(3) Uani 1 1 d . . . . .
O2 O 0.15053(14) 0.58180(12) 0.95550(15) 0.0448(4) Uani 1 1 d . . . . .
O4 O -0.05832(14) 0.63604(14) 0.72456(16) 0.0504(4) Uani 1 1 d . . . . .
O3 O 0.16669(18) 0.52157(14) 0.74612(18) 0.0602(5) Uani 1 1 d . . . . .
N1 N 0.06937(15) 0.72667(15) 0.64620(17) 0.0357(4) Uani 1 1 d . . . . .
H1 H 0.082386 0.764810 0.578961 0.043 Uiso 1 1 calc R U . . .
C9 C 0.15602(17) 0.71200(16) 0.77457(19) 0.0332(4) Uani 1 1 d . . . . .
C12 C -0.03221(17) 0.68218(18) 0.6281(2) 0.0366(4) Uani 1 1 d . . . . .
C10 C 0.15646(19) 0.59374(17) 0.8232(2) 0.0396(5) Uani 1 1 d . . . . .
C7 C 0.26563(19) 0.7336(2) 0.7390(2) 0.0427(5) Uani 1 1 d . . . . .
H7A H 0.263376 0.803787 0.694966 0.051 Uiso 1 1 calc R U . . .
H7B H 0.277195 0.679983 0.672160 0.051 Uiso 1 1 calc R U . . .
C8 C 0.1347(3) 0.89096(18) 0.8596(3) 0.0518(6) Uani 1 1 d . . . . .
H8A H 0.073368 0.905061 0.779581 0.078 Uiso 1 1 calc R U . . .
H8B H 0.201502 0.915671 0.839674 0.078 Uiso 1 1 calc R U . . .
H8C H 0.124094 0.928109 0.941172 0.078 Uiso 1 1 calc R U . . .
C13 C -0.1087(2) 0.6930(2) 0.4832(2) 0.0479(5) Uani 1 1 d . . . . .
H13A H -0.120351 0.623549 0.438657 0.072 Uiso 1 1 calc R U . . .
H13B H -0.076838 0.740601 0.427442 0.072 Uiso 1 1 calc R U . . .
H13C H -0.177975 0.721634 0.490484 0.072 Uiso 1 1 calc R U . . .
C6 C 0.4974(2) 0.6864(2) 0.8153(3) 0.0528(6) Uani 1 1 d . . . . .
C1 C 0.5698(3) 0.7601(3) 0.7867(3) 0.0640(7) Uani 1 1 d . . . . .
H1A H 0.568319 0.831107 0.816396 0.077 Uiso 1 1 calc R U . . .
C11 C 0.1530(3) 0.4707(2) 1.0018(3) 0.0685(8) Uani 1 1 d . . . . .
H11A H 0.096976 0.430572 0.935943 0.103 Uiso 1 1 calc R U . . .
H11B H 0.139716 0.467862 1.094018 0.103 Uiso 1 1 calc R U . . .
H11C H 0.224031 0.440201 1.005922 0.103 Uiso 1 1 calc R U . . .
C3 C 0.6489(3) 0.6260(4) 0.6698(4) 0.0799(10) Uani 1 1 d . . . . .
H3 H 0.700107 0.605830 0.620973 0.096 Uiso 1 1 calc R U . . .
C2 C 0.6456(3) 0.7285(3) 0.7132(4) 0.0740(9) Uani 1 1 d . . . . .
H2 H 0.694616 0.778716 0.693883 0.089 Uiso 1 1 calc R U . . .
C5 C 0.5022(3) 0.5820(3) 0.7713(4) 0.0819(10) Uani 1 1 d . . . . .
H5 H 0.454526 0.530758 0.791572 0.098 Uiso 1 1 calc R U . . .
C4 C 0.5778(3) 0.5524(3) 0.6969(5) 0.0952(12) Uani 1 1 d . . . . .
H4 H 0.579551 0.481846 0.665728 0.114 Uiso 1 1 calc R U . . .


_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
Se1 C7 1.965(2) . ?
Se1 C6 1.928(3) . ?
O1 C9 1.416(2) . ?
O1 C8 1.433(3) . ?
O2 C10 1.323(2) . ?
O2 C11 1.450(3) . ?
O4 C12 1.220(2) . ?
O3 C10 1.200(3) . ?
N1 H1 0.8600 . ?
N1 C9 1.442(3) . ?
N1 C12 1.359(3) . ?
C9 C10 1.544(3) . ?
C9 C7 1.529(3) . ?
C12 C13 1.495(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C6 C1 1.370(4) . ?
C6 C5 1.373(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.390(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.347(5) . ?
C3 C4 1.352(6) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.388(5) . ?
C4 H4 0.9300 . ?

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
C6 Se1 C7 94.99(10) . . ?
C9 O1 C8 115.78(15) . . ?
C10 O2 C11 114.16(18) . . ?
C9 N1 H1 118.9 . . ?
C12 N1 H1 118.9 . . ?
C12 N1 C9 122.11(16) . . ?
O1 C9 N1 112.78(16) . . ?
O1 C9 C10 107.43(15) . . ?
O1 C9 C7 112.03(17) . . ?
N1 C9 C10 109.23(16) . . ?
N1 C9 C7 107.42(15) . . ?
C7 C9 C10 107.81(18) . . ?
O4 C12 N1 121.55(19) . . ?
O4 C12 C13 122.6(2) . . ?
N1 C12 C13 115.85(18) . . ?
O2 C10 C9 114.27(17) . . ?
O3 C10 O2 124.9(2) . . ?
O3 C10 C9 120.70(18) . . ?
Se1 C7 H7A 109.6 . . ?
Se1 C7 H7B 109.6 . . ?
C9 C7 Se1 110.40(14) . . ?
C9 C7 H7A 109.6 . . ?
C9 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C6 Se1 120.8(2) . . ?
C1 C6 C5 118.9(3) . . ?
C5 C6 Se1 120.3(2) . . ?
C6 C1 H1A 120.1 . . ?
C6 C1 C2 119.7(3) . . ?
C2 C1 H1A 120.1 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?

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
Se1 C6 C1 C2 -178.0(2) . . . . ?
Se1 C6 C5 C4 177.4(3) . . . . ?
O1 C9 C10 O2 -3.5(2) . . . . ?
O1 C9 C10 O3 179.8(2) . . . . ?
O1 C9 C7 Se1 50.4(2) . . . . ?
N1 C9 C10 O2 -126.10(19) . . . . ?
N1 C9 C10 O3 57.2(3) . . . . ?
N1 C9 C7 Se1 174.80(14) . . . . ?
C9 N1 C12 O4 7.0(3) . . . . ?
C9 N1 C12 C13 -172.66(19) . . . . ?
C12 N1 C9 O1 -77.4(2) . . . . ?
C12 N1 C9 C10 42.0(2) . . . . ?
C12 N1 C9 C7 158.66(19) . . . . ?
C10 C9 C7 Se1 -67.59(18) . . . . ?
C7 C9 C10 O2 117.5(2) . . . . ?
C7 C9 C10 O3 -59.3(3) . . . . ?
C8 O1 C9 N1 -56.7(2) . . . . ?
C8 O1 C9 C10 -177.2(2) . . . . ?
C8 O1 C9 C7 64.6(2) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C6 C5 C4 C3 1.4(7) . . . . ?
C1 C6 C5 C4 -1.2(5) . . . . ?
C11 O2 C10 O3 -2.4(4) . . . . ?
C11 O2 C10 C9 -178.9(2) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C5 C6 C1 C2 0.6(5) . . . . ?
C4 C3 C2 C1 0.2(5) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.721
