# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_chenshanchong_x7-2_collect
_database_code_depnum_ccdc_archive 'CCDC 1974672'
loop_
_audit_author_name
_audit_author_address
'Trieffnol C'
;Guangdong Institute of Microbiology
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-10-21 downloaded from the CCDC.
;
_audit_creation_date             2019-08-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        'Trieffnol C'
_chemical_formula_moiety         'H2 O, C26 H26 O7'
_chemical_formula_sum            'C26 H28 O8'
_chemical_formula_weight         468.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C52 H56 O16 '
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'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3229(2)
_cell_length_b                   10.5201(2)
_cell_length_c                   13.8336(3)
_cell_angle_alpha                88.816(2)
_cell_angle_beta                 73.989(2)
_cell_angle_gamma                76.976(2)
_cell_volume                     1133.19(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5339
_cell_measurement_temperature    99.9(9)
_cell_measurement_theta_max      61.9040
_cell_measurement_theta_min      5.3270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             496
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.847
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9494
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.033
_diffrn_reflns_theta_min         4.318
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.847
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  62.00   0.50    0.71    --    0.00  57.00-120.00   56
  2  ω    -54.00 -29.00   0.50    0.71    --    0.00 -57.00-120.00   50
  3  ω      3.00  29.00   0.50    0.71    --    0.00 -82.00  90.00   52
  4  ω    -16.00  16.00   0.50    0.71    --    0.00  57.00-120.00   64
  5  ω    -15.00  12.00   0.50    0.71    --    0.00 -57.00-120.00   54
  6  ω    -17.00  93.00   0.50    2.84    --   70.80 -61.00  60.00  220
  7  ω     21.00 102.00   0.50    2.84    --   70.80 -82.00-180.00  162
  8  ω    -18.00  99.00   0.50    2.84    --   70.80 -82.00 -60.00  234
  9  ω     52.00  78.00   0.50    2.84    --   70.80  61.00 -60.00   52
 10  ω     36.00  79.00   0.50    2.84    --   70.80 -61.00-180.00   86
 11  ω    -19.00   6.00   0.50    2.84    --   70.80 -82.00-180.00   50
 12  ω    -10.00  20.00   0.50    2.84    --   70.80 -61.00-180.00   60
 13  ω     53.00 101.00   0.50    2.84    --   70.80  45.00 -60.00   96
 14  ω    129.00 158.00   0.50    2.84    --   70.80  45.00 -60.00   58
 15  ω     58.00  94.00   0.50    2.84    --   70.80 -82.00 120.00   72
 16  ω     11.00  38.00   0.50    2.84    --   70.80 -82.00 120.00   54
 17  ω    -10.00  15.00   0.50    2.84    --   70.80 -82.00  30.00   50
 18  ω     42.00  95.00   0.50    2.84    --   70.80 -82.00  30.00  106
 19  ω      3.00  93.00   0.50    2.84    --   70.80 -61.00 -60.00  180
 20  ω    101.00 159.00   0.50    2.84    --   70.80  82.00 -30.00  116
 21  ω    -16.00  98.00   0.50    2.84    --   70.80 -82.00  60.00  228
 22  ω    109.00 136.00   0.50    2.84    --   70.80  61.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1503241000
_diffrn_orient_matrix_UB_12      0.0656972000
_diffrn_orient_matrix_UB_13      -0.0068889000
_diffrn_orient_matrix_UB_21      0.1284920000
_diffrn_orient_matrix_UB_22      -0.1309834000
_diffrn_orient_matrix_UB_23      -0.0378523000
_diffrn_orient_matrix_UB_31      0.0044498000
_diffrn_orient_matrix_UB_32      0.0341142000
_diffrn_orient_matrix_UB_33      -0.1094038000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3022
_reflns_number_total             3468
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.141
_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1391
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O0AA(H0AA,H0AB)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C13(H13), C14(H14), C16(H16), C17(H17), C22(H22)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O5(H5), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O0AA O -0.83108(17) 0.29760(14) 0.93943(10) 0.0325(4) Uani 1 1 d . . . . .
H0AA H -0.8866 0.2945 0.8967 0.049 Uiso 1 1 d G . . . .
H0AB H -0.8992 0.2860 0.9955 0.049 Uiso 1 1 d G . . . .
O1 O 0.43316(15) 0.61866(12) 0.63638(9) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.66927(15) 0.15722(12) 0.55094(9) 0.0264(3) Uani 1 1 d . . . . .
H2 H 0.6469 0.0869 0.5687 0.040 Uiso 1 1 calc GR . . . .
O3 O 0.08419(14) 0.33125(11) 0.74582(8) 0.0203(3) Uani 1 1 d . . . . .
O4 O -0.72513(15) 0.52435(12) 0.92085(9) 0.0255(3) Uani 1 1 d . . . . .
H4 H -0.7515 0.4535 0.9291 0.038 Uiso 1 1 calc GR . . . .
O5 O 0.06667(16) 0.74212(12) 0.87932(8) 0.0239(3) Uani 1 1 d . . . . .
H5 H 0.1371 0.6719 0.8692 0.036 Uiso 1 1 calc GR . . . .
O6 O -0.14074(17) 1.08376(11) 0.68950(10) 0.0286(3) Uani 1 1 d . . . . .
H6 H -0.1910 1.0945 0.6456 0.043 Uiso 1 1 calc GR . . . .
O7 O 0.01863(15) 0.63866(11) 0.55753(9) 0.0231(3) Uani 1 1 d . . . . .
C1 C 0.4237(2) 0.49056(17) 0.63669(12) 0.0208(4) Uani 1 1 d . . . . .
C2 C 0.5575(2) 0.38628(18) 0.59429(13) 0.0228(4) Uani 1 1 d . . . . .
H2A H 0.6649 0.4009 0.5613 0.027 Uiso 1 1 calc R . . . .
C3 C 0.5330(2) 0.25857(17) 0.60057(13) 0.0227(4) Uani 1 1 d . . . . .
C4 C 0.3801(2) 0.22586(17) 0.65290(13) 0.0215(4) Uani 1 1 d . . . . .
C5 C 0.2509(2) 0.33598(17) 0.69419(12) 0.0200(4) Uani 1 1 d . . . . .
C6 C 0.2632(2) 0.46485(16) 0.68471(12) 0.0195(4) Uani 1 1 d . . . . .
C7 C 0.6012(2) 0.64288(19) 0.60343(14) 0.0276(4) Uani 1 1 d . . . . .
H7A H 0.6526 0.6133 0.5343 0.041 Uiso 1 1 calc GR . . . .
H7B H 0.6702 0.5968 0.6440 0.041 Uiso 1 1 calc GR . . . .
H7C H 0.5939 0.7348 0.6098 0.041 Uiso 1 1 calc GR . . . .
C8 C 0.3521(2) 0.08914(18) 0.66082(14) 0.0278(4) Uani 1 1 d . . . . .
H8A H 0.4147 0.0405 0.5978 0.033 Uiso 1 1 calc R . . . .
H8B H 0.2310 0.0930 0.6709 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4094(3) 0.0160(2) 0.74650(16) 0.0361(5) Uani 1 1 d . . . . .
H9A H 0.3861 -0.0694 0.7486 0.054 Uiso 1 1 calc GR . . . .
H9B H 0.3479 0.0634 0.8092 0.054 Uiso 1 1 calc GR . . . .
H9C H 0.5304 0.0082 0.7355 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.0935(2) 0.54514(16) 0.72778(12) 0.0186(4) Uani 1 1 d . . . . .
C11 C -0.0103(2) 0.46155(16) 0.76351(12) 0.0194(4) Uani 1 1 d . . . . .
C12 C -0.1949(2) 0.47648(16) 0.80848(12) 0.0197(4) Uani 1 1 d . . . . .
C13 C -0.2697(2) 0.36929(17) 0.81353(13) 0.0222(4) Uani 1 1 d . . . . .
H13 H -0.2002 0.2872 0.7909 0.027 Uiso 1 1 calc R . . . .
C14 C -0.4448(2) 0.38291(18) 0.85136(13) 0.0242(4) Uani 1 1 d . . . . .
H14 H -0.4919 0.3102 0.8546 0.029 Uiso 1 1 calc R . . . .
C15 C -0.5505(2) 0.50491(17) 0.88457(12) 0.0216(4) Uani 1 1 d . . . . .
C16 C -0.4785(2) 0.61251(17) 0.88094(13) 0.0240(4) Uani 1 1 d . . . . .
H16 H -0.5488 0.6944 0.9035 0.029 Uiso 1 1 calc R . . . .
C17 C -0.3040(2) 0.59882(17) 0.84428(13) 0.0235(4) Uani 1 1 d . . . . .
H17 H -0.2574 0.6715 0.8431 0.028 Uiso 1 1 calc R . . . .
C18 C 0.0397(2) 0.68810(17) 0.71756(12) 0.0195(4) Uani 1 1 d . . . . .
C19 C 0.0272(2) 0.77990(17) 0.79150(12) 0.0200(4) Uani 1 1 d . . . . .
C20 C -0.0325(2) 0.91392(17) 0.78375(13) 0.0221(4) Uani 1 1 d . . . . .
C21 C -0.0776(2) 0.95370(17) 0.69643(13) 0.0227(4) Uani 1 1 d . . . . .
C22 C -0.0590(2) 0.86541(17) 0.61783(13) 0.0221(4) Uani 1 1 d . . . . .
H22 H -0.0848 0.8948 0.5588 0.027 Uiso 1 1 calc R . . . .
C23 C -0.0016(2) 0.73399(17) 0.62941(13) 0.0205(4) Uani 1 1 d . . . . .
C24 C -0.0554(3) 1.01120(18) 0.86790(14) 0.0278(4) Uani 1 1 d . . . . .
H24A H -0.0298 1.0917 0.8392 0.033 Uiso 1 1 calc R . . . .
H24B H 0.0259 0.9770 0.9059 0.033 Uiso 1 1 calc R . . . .
C25 C -0.2363(3) 1.0409(2) 0.93907(15) 0.0374(5) Uani 1 1 d . . . . .
H25A H -0.3173 1.0750 0.9020 0.056 Uiso 1 1 calc GR . . . .
H25B H -0.2449 1.1042 0.9903 0.056 Uiso 1 1 calc GR . . . .
H25C H -0.2608 0.9622 0.9698 0.056 Uiso 1 1 calc GR . . . .
C26 C -0.0197(2) 0.67973(18) 0.46536(13) 0.0241(4) Uani 1 1 d . . . . .
H26A H -0.0075 0.6044 0.4237 0.036 Uiso 1 1 calc GR . . . .
H26B H 0.0582 0.7314 0.4307 0.036 Uiso 1 1 calc GR . . . .
H26C H -0.1354 0.7309 0.4799 0.036 Uiso 1 1 calc GR . . . .


_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
O1 C1 1.367(2) . ?
O1 C7 1.426(2) . ?
O2 C3 1.397(2) . ?
O3 C5 1.386(2) . ?
O3 C11 1.407(2) . ?
O4 C15 1.369(2) . ?
O5 C19 1.3723(19) . ?
O6 C21 1.362(2) . ?
O7 C23 1.377(2) . ?
O7 C26 1.433(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.401(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.397(2) . ?
C4 C8 1.505(3) . ?
C5 C6 1.383(2) . ?
C6 C10 1.443(2) . ?
C8 C9 1.527(3) . ?
C10 C11 1.361(2) . ?
C10 C18 1.485(2) . ?
C11 C12 1.463(2) . ?
C12 C13 1.398(3) . ?
C12 C17 1.406(2) . ?
C13 C14 1.380(3) . ?
C14 C15 1.387(2) . ?
C15 C16 1.389(3) . ?
C16 C17 1.375(3) . ?
C18 C19 1.388(2) . ?
C18 C23 1.404(2) . ?
C19 C20 1.398(2) . ?
C20 C21 1.391(2) . ?
C20 C24 1.509(2) . ?
C21 C22 1.398(2) . ?
C22 C23 1.379(3) . ?
C24 C25 1.522(3) . ?

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
C1 O1 C7 116.19(13) . . ?
C5 O3 C11 106.36(13) . . ?
C23 O7 C26 117.63(13) . . ?
O1 C1 C2 125.67(17) . . ?
O1 C1 C6 116.27(15) . . ?
C2 C1 C6 118.06(17) . . ?
C1 C2 C3 120.56(17) . . ?
O2 C3 C2 118.36(16) . . ?
C4 C3 O2 117.54(16) . . ?
C4 C3 C2 124.10(15) . . ?
C3 C4 C5 112.11(16) . . ?
C3 C4 C8 124.70(15) . . ?
C5 C4 C8 123.13(16) . . ?
O3 C5 C4 123.84(16) . . ?
C6 C5 O3 109.44(14) . . ?
C6 C5 C4 126.57(17) . . ?
C1 C6 C10 134.43(16) . . ?
C5 C6 C1 118.29(16) . . ?
C5 C6 C10 107.25(15) . . ?
C4 C8 C9 113.37(15) . . ?
C6 C10 C18 125.75(15) . . ?
C11 C10 C6 106.28(15) . . ?
C11 C10 C18 127.10(15) . . ?
O3 C11 C12 114.49(15) . . ?
C10 C11 O3 110.55(15) . . ?
C10 C11 C12 134.79(16) . . ?
C13 C12 C11 120.60(15) . . ?
C13 C12 C17 117.69(16) . . ?
C17 C12 C11 121.66(16) . . ?
C14 C13 C12 121.31(16) . . ?
C13 C14 C15 120.10(17) . . ?
O4 C15 C14 122.50(17) . . ?
O4 C15 C16 118.03(15) . . ?
C14 C15 C16 119.47(16) . . ?
C17 C16 C15 120.47(16) . . ?
C16 C17 C12 120.94(17) . . ?
C19 C18 C10 123.19(15) . . ?
C19 C18 C23 117.76(16) . . ?
C23 C18 C10 119.04(15) . . ?
O5 C19 C18 120.93(15) . . ?
O5 C19 C20 116.14(15) . . ?
C18 C19 C20 122.87(16) . . ?
C19 C20 C24 121.92(16) . . ?
C21 C20 C19 116.94(16) . . ?
C21 C20 C24 121.08(16) . . ?
O6 C21 C20 117.36(15) . . ?
O6 C21 C22 120.48(15) . . ?
C20 C21 C22 122.16(16) . . ?
C23 C22 C21 118.77(16) . . ?
O7 C23 C18 115.09(15) . . ?
O7 C23 C22 123.53(15) . . ?
C22 C23 C18 121.37(16) . . ?
C20 C24 C25 112.67(16) . . ?

_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 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.679
