# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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. 
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data_cis042_a
_audit_block_doi                 10.5517/ccdc.csd.cc25mwmb
_database_code_depnum_ccdc_archive 'CCDC 2015112'
loop_
_audit_author_name
_audit_author_address
'Leona S. Flores'
;Federal University of Juiz de Fora
Brazil
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2024-11-26 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 K N O3'
_chemical_formula_sum            'C5 H3 K N O3'
_chemical_formula_weight         164.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
K K 0.2009 0.2494 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   7.2425(2)
_cell_length_b                   26.0431(9)
_cell_length_c                   6.4409(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1214.86(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8304
_cell_measurement_temperature    292.92(10)
_cell_measurement_theta_max      28.5290
_cell_measurement_theta_min      4.2100
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.775
_diffrn_reflns_theta_min         3.258
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.92(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  40.00   1.00    7.88    --   11.79 -57.00   0.00  101
  2  ω    -20.00  53.00   1.00    7.88    --   11.79 -99.00-120.00   73
  3  ω    -16.00  85.00   1.00    7.88    --   11.79  57.00 -60.00  101
  4  ω    -16.00  85.00   1.00    7.88    --   11.79  57.00 150.00  101
  5  ω    -13.00  86.00   1.00    7.88    --   11.79  38.00  60.00   99
  6  ω    -20.00  53.00   1.00    7.88    --   11.79 -99.00 150.00   73
  7  ω    -20.00  53.00   1.00    7.88    --   11.79 -99.00 120.00   73
  8  ω    -15.00  56.00   1.00    7.88    --   11.79-105.00 -43.00   71
  9  ω     34.00  99.00   1.00    7.88    --   11.79-178.00  30.00   65
 10  ω    -20.00  29.00   1.00    7.88    --  -12.03 -99.00 150.00   49
 11  ω    -20.00  23.00   1.00    7.88    --   11.79 -99.00  60.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0244805000
_diffrn_orient_matrix_UB_12      -0.0261066000
_diffrn_orient_matrix_UB_13      0.0151731000
_diffrn_orient_matrix_UB_21      0.0129398000
_diffrn_orient_matrix_UB_22      -0.0029224000
_diffrn_orient_matrix_UB_23      -0.1084820000
_diffrn_orient_matrix_UB_31      0.0939519000
_diffrn_orient_matrix_UB_32      0.0072157000
_diffrn_orient_matrix_UB_33      0.0109892000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1492
_reflns_number_total             1697
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1697
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.066
_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)+(0.0293P)²+0.9832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0793
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C5(H5)
;
_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
K1 K 0.30664(5) 0.54450(2) 0.28941(6) 0.02679(12) Uani 1 1 d . . . . .
O1 O 0.42887(18) 0.53546(5) 0.7135(2) 0.0343(3) Uani 1 1 d . . . . .
O3 O 0.52473(18) 0.58523(5) 0.97623(19) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.57179(19) 0.60678(5) 0.44393(19) 0.0363(3) Uani 1 1 d . . . . .
N1 N 0.6377(2) 0.65787(5) 0.7204(2) 0.0247(3) Uani 1 1 d . . . . .
H1 H 0.647802 0.657743 0.853429 0.030 Uiso 1 1 calc R U . . .
C1 C 0.5026(2) 0.57433(6) 0.7898(3) 0.0233(3) Uani 1 1 d . . . . .
C4 C 0.6465(3) 0.750000 0.7125(3) 0.0228(4) Uani 1 2 d S T P . .
H4 H 0.589264 0.750000 0.841778 0.027 Uiso 1 2 calc R U P . .
C2 C 0.5746(2) 0.61455(6) 0.6307(2) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.6893(2) 0.70369(6) 0.6161(3) 0.0228(3) Uani 1 1 d . . . . .
C6 C 0.8212(3) 0.750000 0.3310(4) 0.0284(5) Uani 1 2 d S T P . .
H6 H 0.880859 0.750000 0.203179 0.034 Uiso 1 2 calc R U P . .
C5 C 0.7778(2) 0.70342(6) 0.4241(3) 0.0272(3) Uani 1 1 d . . . . .
H5 H 0.807350 0.672585 0.359268 0.033 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
K1 K1 4.0518(4) 2_564 ?
K1 K1 3.65667(14) 6_656 ?
K1 K1 3.65666(14) 6_556 ?
K1 O1 2.8296(14) 5_666 ?
K1 O1 2.7358(12) 2_564 ?
K1 O1 2.8813(14) . ?
K1 O3 2.7729(13) 1_554 ?
K1 O3 2.7518(13) 6_557 ?
K1 O2 2.7896(14) 6_556 ?
K1 O2 2.7035(13) . ?
K1 C1 3.4274(16) 5_666 ?
K1 C2 3.4533(16) . ?
O1 C1 1.245(2) . ?
O3 C1 1.244(2) . ?
O2 C2 1.220(2) . ?
N1 H1 0.8600 . ?
N1 C2 1.348(2) . ?
N1 C3 1.419(2) . ?
C1 C2 1.555(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.3914(19) . ?
C4 C3 1.3914(19) 7_575 ?
C3 C5 1.393(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.389(2) 7_575 ?
C6 C5 1.389(2) . ?
C5 H5 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
K1 K1 K1 71.889(14) 6_556 2_564 ?
K1 K1 K1 95.173(14) 6_656 2_564 ?
K1 K1 K1 164.04(2) 6_556 6_656 ?
O1 K1 K1 50.04(3) 2_564 6_556 ?
O1 K1 K1 47.83(3) 5_666 6_656 ?
O1 K1 K1 73.18(3) 5_666 2_564 ?
O1 K1 K1 80.06(3) . 6_656 ?
O1 K1 K1 140.27(3) . 2_564 ?
O1 K1 K1 45.28(3) 2_564 2_564 ?
O1 K1 K1 132.03(3) 5_666 6_556 ?
O1 K1 K1 115.84(3) . 6_556 ?
O1 K1 K1 126.34(3) 2_564 6_656 ?
O1 K1 O1 107.38(4) 2_564 . ?
O1 K1 O1 74.82(4) 5_666 . ?
O1 K1 O1 81.99(3) 2_564 5_666 ?
O1 K1 O3 121.09(4) 2_564 1_554 ?
O1 K1 O3 85.92(4) 2_564 6_557 ?
O1 K1 O2 88.06(4) 2_564 6_556 ?
O1 K1 C1 62.45(4) 2_564 5_666 ?
O1 K1 C1 20.21(4) 5_666 5_666 ?
O1 K1 C1 86.76(4) . 5_666 ?
O1 K1 C2 90.73(4) 5_666 . ?
O1 K1 C2 42.87(4) . . ?
O1 K1 C2 150.02(4) 2_564 . ?
O3 K1 K1 117.59(3) 1_554 6_556 ?
O3 K1 K1 48.81(3) 6_557 6_556 ?
O3 K1 K1 144.19(3) 6_557 6_656 ?
O3 K1 K1 120.42(3) 6_557 2_564 ?
O3 K1 K1 48.31(3) 1_554 6_656 ?
O3 K1 K1 75.88(3) 1_554 2_564 ?
O3 K1 O1 142.16(4) 6_557 5_666 ?
O3 K1 O1 83.74(4) 1_554 5_666 ?
O3 K1 O1 123.09(4) 1_554 . ?
O3 K1 O1 74.89(4) 6_557 . ?
O3 K1 O3 132.39(5) 6_557 1_554 ?
O3 K1 O2 74.51(4) 1_554 6_556 ?
O3 K1 O2 67.61(4) 6_557 6_556 ?
O3 K1 C1 136.78(4) 6_557 5_666 ?
O3 K1 C1 90.43(4) 1_554 5_666 ?
O3 K1 C2 86.61(4) 1_554 . ?
O3 K1 C2 82.19(4) 6_557 . ?
O2 K1 K1 49.28(3) . 6_656 ?
O2 K1 K1 77.35(3) 6_556 2_564 ?
O2 K1 K1 138.99(3) . 6_556 ?
O2 K1 K1 121.94(3) 6_556 6_656 ?
O2 K1 K1 47.27(3) 6_556 6_556 ?
O2 K1 K1 141.23(3) . 2_564 ?
O2 K1 O1 164.85(4) . 2_564 ?
O2 K1 O1 87.89(4) . 5_666 ?
O2 K1 O1 58.78(4) . . ?
O2 K1 O1 138.21(4) 6_556 . ?
O2 K1 O1 146.83(4) 6_556 5_666 ?
O2 K1 O3 95.39(4) . 6_557 ?
O2 K1 O3 68.51(4) . 1_554 ?
O2 K1 O2 106.42(5) . 6_556 ?
O2 K1 C1 133.68(4) 6_556 5_666 ?
O2 K1 C1 108.07(4) . 5_666 ?
O2 K1 C2 18.12(4) . . ?
O2 K1 C2 112.23(4) 6_556 . ?
C1 K1 K1 112.24(3) 5_666 6_556 ?
C1 K1 K1 56.41(3) 5_666 2_564 ?
C1 K1 K1 65.18(3) 5_666 6_656 ?
C1 K1 C2 110.20(4) 5_666 . ?
C2 K1 K1 157.21(3) . 2_564 ?
C2 K1 K1 62.09(3) . 6_656 ?
C2 K1 K1 130.15(3) . 6_556 ?
K1 O1 K1 92.29(4) 2_565 . ?
K1 O1 K1 105.17(4) 5_666 . ?
K1 O1 K1 82.13(3) 2_565 5_666 ?
C1 O1 K1 108.10(10) . 5_666 ?
C1 O1 K1 116.04(10) . . ?
C1 O1 K1 144.65(12) . 2_565 ?
K1 O3 K1 82.89(3) 6_657 1_556 ?
C1 O3 K1 122.78(11) . 1_556 ?
C1 O3 K1 122.48(11) . 6_657 ?
K1 O2 K1 83.45(3) . 6_656 ?
C2 O2 K1 118.31(11) . . ?
C2 O2 K1 128.15(12) . 6_656 ?
C2 N1 H1 116.9 . . ?
C2 N1 C3 126.17(14) . . ?
C3 N1 H1 116.9 . . ?
O1 C1 K1 51.69(9) . 5_666 ?
O1 C1 C2 115.56(14) . . ?
O3 C1 K1 107.32(10) . 5_666 ?
O3 C1 O1 128.39(15) . . ?
O3 C1 C2 116.05(14) . . ?
C2 C1 K1 112.02(9) . 5_666 ?
C3 C4 H4 119.9 7_575 . ?
C3 C4 H4 119.9 . . ?
C3 C4 C3 120.2(2) . 7_575 ?
O2 C2 K1 43.57(8) . . ?
O2 C2 N1 124.57(15) . . ?
O2 C2 C1 122.16(14) . . ?
N1 C2 K1 154.96(11) . . ?
N1 C2 C1 113.27(13) . . ?
C1 C2 K1 82.83(8) . . ?
C4 C3 N1 117.32(15) . . ?
C4 C3 C5 120.21(15) . . ?
C5 C3 N1 122.47(14) . . ?
C5 C6 H6 119.1 . . ?
C5 C6 H6 119.1 7_575 . ?
C5 C6 C5 121.7(2) 7_575 . ?
C3 C5 H5 120.6 . . ?
C6 C5 C3 118.86(16) . . ?
C6 C5 H5 120.6 . . ?

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
K1 O1 C1 K1 -117.79(11) . . . 5_666 ?
K1 O1 C1 K1 102.23(18) 2_565 . . 5_666 ?
K1 O1 C1 O3 160.37(15) . . . . ?
K1 O1 C1 O3 -81.84(19) 5_666 . . . ?
K1 O1 C1 O3 20.4(3) 2_565 . . . ?
K1 O1 C1 C2 98.74(13) 5_666 . . . ?
K1 O1 C1 C2 -19.05(17) . . . . ?
K1 O1 C1 C2 -159.03(13) 2_565 . . . ?
K1 O3 C1 K1 25.75(13) 6_657 . . 5_666 ?
K1 O3 C1 K1 -77.87(11) 1_556 . . 5_666 ?
K1 O3 C1 O1 -23.4(2) 1_556 . . . ?
K1 O3 C1 O1 80.2(2) 6_657 . . . ?
K1 O3 C1 C2 156.01(10) 1_556 . . . ?
K1 O3 C1 C2 -100.38(14) 6_657 . . . ?
K1 O2 C2 K1 -104.98(14) 6_656 . . . ?
K1 O2 C2 N1 104.32(17) 6_656 . . . ?
K1 O2 C2 N1 -150.70(13) . . . . ?
K1 O2 C2 C1 29.0(2) . . . . ?
K1 O2 C2 C1 -76.00(19) 6_656 . . . ?
K1 C1 C2 K1 71.06(6) 5_666 . . . ?
K1 C1 C2 O2 51.40(19) 5_666 . . . ?
K1 C1 C2 N1 -128.89(12) 5_666 . . . ?
O1 C1 C2 K1 14.28(13) . . . . ?
O1 C1 C2 O2 -5.4(2) . . . . ?
O1 C1 C2 N1 174.32(15) . . . . ?
O3 C1 C2 K1 -165.22(14) . . . . ?
O3 C1 C2 O2 175.11(17) . . . . ?
O3 C1 C2 N1 -5.2(2) . . . . ?
N1 C3 C5 C6 179.10(18) . . . . ?
C4 C3 C5 C6 -0.4(3) . . . . ?
C2 N1 C3 C4 142.71(18) . . . . ?
C2 N1 C3 C5 -36.8(2) . . . . ?
C3 N1 C2 K1 -44.4(3) . . . . ?
C3 N1 C2 O2 8.4(3) . . . . ?
C3 N1 C2 C1 -171.27(14) . . . . ?
C3 C4 C3 N1 -178.44(14) 7_575 . . . ?
C3 C4 C3 C5 1.1(3) 7_575 . . . ?
C5 C6 C5 C3 -0.3(4) 7_575 . . . ?

_olex2_date_sample_data_collection 2016-08-24
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.206
_oxdiff_exptl_absorpt_empirical_full_min 0.822
