# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_bx1_1023
_database_code_depnum_ccdc_archive 'CCDC 2272292'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;University of Toyama
Japan
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-10-23
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Coerulein B'
_chemical_formula_moiety         'C20 H10 O4'
_chemical_formula_sum            'C20 H10 O4'
_chemical_formula_weight         314.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C77 H77 O77 '
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.7163(5)
_cell_length_b                   11.3800(3)
_cell_length_c                   18.1174(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.795(3)
_cell_angle_gamma                90
_cell_volume                     2734.21(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3767
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.2230
_cell_measurement_theta_min      3.6090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -5 0 0.0688
0 -3 -10 0.0385
0 -7 -2 0.0157
5 -5 -8 0.0495
0 -6 6 0.0163
-1 -4 10 0.0350
9 1 -5 0.0649
7 -2 3 0.0622
8 2 -3 0.0623
0 6 7 0.0478
0 7 -4 0.0502
-4 7 1 0.0800
0 5 -8 0.0499

_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.067
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.3024 -5.0567 0.1438 0.1835 0.7564 0.6278
-0.3738 -3.4697 -9.8994 0.2180 0.9095 -0.3541
-0.0747 -7.3057 -1.6323 -0.4630 0.8549 0.2338
4.7825 -4.5409 -8.1813 -0.4010 0.7368 -0.5444
0.1092 -6.3669 5.7246 -0.7384 0.3541 0.5739
-0.8789 -3.7283 10.0504 -0.6469 -0.1178 0.7534
8.7043 0.5015 -5.2190 -0.5107 -0.0964 -0.8543
7.3806 -2.3420 2.7403 -0.9586 -0.1777 -0.2224
8.4722 2.2748 -3.0023 -0.4572 -0.3926 -0.7980
-0.2984 6.0466 6.6164 0.1804 -0.9774 0.1103
-0.0275 6.9706 -3.7480 0.6876 -0.5267 -0.4998
-4.1617 6.5270 1.4957 0.7914 -0.6081 0.0623
-0.0443 5.1393 -8.1524 0.7498 -0.0975 -0.6544

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6756
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.207
_diffrn_reflns_theta_min         4.634
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  14.00   0.50    1.33    --   41.13 -12.00 -30.00   92
  2  ω    -29.00   4.00   0.50    1.33    --   41.13 -12.00-120.00   66
  3  ω     34.00  69.00   0.50    5.33    --   95.43 -59.00-120.00   70
  4  ω     76.00 107.00   0.50    5.33    --   95.43 -99.00-107.00   62
  5  ω     44.00  77.00   0.50    1.33    --   41.13 -99.00-107.00   66
  6  ω     29.00  57.00   0.50    5.33    --   95.43 -50.00   0.00   56
  7  ω     33.00 100.00   0.50    5.33    --   95.43 -77.00  90.00  134
  8  ω     73.00  99.00   0.50    1.33    --   41.13-138.00  60.00   52
  9  ω     45.00  79.00   0.50    1.33    --   41.13-104.00  90.00   68
 10  ω     31.00  56.00   0.50    5.33    --   95.43 -50.00 150.00   50
 11  ω     28.00  69.00   0.50    5.33    --   95.43 -59.00 150.00   82
 12  ω     29.00  54.00   0.50    5.33    --   95.43 -50.00  90.00   50
 13  ω     29.00  65.00   0.50    5.33    --   95.43 -59.00  90.00   72
 14  ω     30.00 117.00   0.50    5.33    --   95.43-145.00 120.00  174
 15  ω     -3.00  33.00   0.50    1.33    --   41.13-104.00  90.00   72
 16  ω    -22.00  33.00   0.50    1.33    --  -41.44  12.00 -60.00  110
 17  ω    -28.00  26.00   0.50    1.33    --  -41.44  25.00   0.00  108
 18  ω    -39.00  23.00   0.50    1.33    --  -41.44  99.00  -1.00  124
 19  ω    -55.00 -29.00   0.50    5.33    --  -95.75  50.00   0.00   52
 20  ω    -57.00 -32.00   0.50    5.33    --  -95.75  50.00 -30.00   50
 21  ω    -62.00 -28.00   0.50    5.33    --  -95.75  68.00 -30.00   68
 22  ω    -94.00 -23.00   0.50    5.33    --  -95.75  99.00  -1.00  142
 23  ω    -57.00 -32.00   0.50    5.33    --  -95.75  50.00 150.00   50
 24  ω   -130.00-103.00   0.50    5.33    --  -95.75 -99.00-107.00   54
 25  ω    -12.00  40.00   0.50    1.33    --   41.13 -99.00-107.00  104
 26  ω     27.00 106.00   0.50    5.33    --   95.43 -77.00-120.00  158
 27  ω     82.00 118.00   0.50    5.33    --   95.43  42.00-180.00   72
 28  ω    120.00 167.00   0.50    5.33    --   95.43  96.00-150.00   94
 29  ω     84.00 111.00   0.50    5.33    --   95.43  96.00-150.00   54
 30  ω     78.00 125.00   0.50    5.33    --   95.43 117.00-120.00   94
 31  ω     72.00  98.00   0.50    1.33    --   41.13 138.00-120.00   52
 32  ω     82.00 107.00   0.50    1.33    --   41.13 138.00 -90.00   50
 33  ω     91.00 143.00   0.50    5.33    --   95.43  99.00  -1.00  104
 34  ω     84.00 109.00   0.50    1.33    --   41.13 138.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0897331000
_diffrn_orient_matrix_UB_12      0.0742735000
_diffrn_orient_matrix_UB_13      -0.0446622000
_diffrn_orient_matrix_UB_21      -0.0373047000
_diffrn_orient_matrix_UB_22      -0.1046252000
_diffrn_orient_matrix_UB_23      -0.0537903000
_diffrn_orient_matrix_UB_31      -0.0636730000
_diffrn_orient_matrix_UB_32      -0.0432760000
_diffrn_orient_matrix_UB_33      0.0533410000
_diffrn_oxdiff_digest_frames     
;
01f238518ce032bfcfec72a16bd5a422f102756ca4a
;
_diffrn_oxdiff_digest_hkl        
;
013c79e321185766285f9fd41f9b782164d6ef
;
_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                2301
_reflns_number_total             2482
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.091
_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)+(0.0605P)²+3.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1332
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C2(H2), C10(H10), C15(H15), C5(H5), C4(H4), C18(H18), C16(H16),
 C17(H17)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O1 O 0.36247(9) 0.37211(12) 0.56048(7) 0.0274(3) Uani 1 1 d . . . . .
O3 O 0.36758(11) 0.40965(14) 0.30160(7) 0.0350(4) Uani 1 1 d . . . . .
H3 H 0.365854 0.336058 0.304632 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.37331(12) 0.31126(14) 0.81767(8) 0.0432(4) Uani 1 1 d . . . . .
O4 O 0.44683(12) 0.81363(13) 0.41285(9) 0.0423(4) Uani 1 1 d . . . . .
C8 C 0.37740(12) 0.56539(17) 0.51074(10) 0.0263(4) Uani 1 1 d . . . . .
C13 C 0.36948(12) 0.44344(17) 0.50123(10) 0.0259(4) Uani 1 1 d . . . . .
C7 C 0.37645(13) 0.61773(17) 0.58282(10) 0.0267(4) Uani 1 1 d . . . . .
C9 C 0.39002(13) 0.63141(18) 0.44780(11) 0.0283(4) Uani 1 1 d . . . . .
C1 C 0.37508(13) 0.41759(17) 0.63238(10) 0.0263(4) Uani 1 1 d . . . . .
C11 C 0.37298(13) 0.45650(19) 0.37004(10) 0.0290(4) Uani 1 1 d . . . . .
C6 C 0.38424(13) 0.54294(17) 0.64460(10) 0.0268(4) Uani 1 1 d . . . . .
C12 C 0.36582(13) 0.38842(18) 0.43264(10) 0.0281(4) Uani 1 1 d . . . . .
H12 H 0.358546 0.305526 0.428078 0.034 Uiso 1 1 calc R . . . .
C2 C 0.37216(14) 0.33929(19) 0.68804(10) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.364336 0.257883 0.676419 0.036 Uiso 1 1 calc R . . . .
C14 C 0.36756(13) 0.74672(18) 0.58498(10) 0.0295(4) Uani 1 1 d . . . . .
C20 C 0.41348(14) 0.75804(19) 0.45891(11) 0.0324(5) Uani 1 1 d . . . . .
C10 C 0.38764(13) 0.57823(19) 0.37906(10) 0.0304(4) Uani 1 1 d . . . . .
H10 H 0.395998 0.624361 0.337398 0.037 Uiso 1 1 calc R . . . .
C19 C 0.39178(14) 0.81448(18) 0.52677(11) 0.0321(4) Uani 1 1 d . . . . .
C15 C 0.33066(15) 0.80626(19) 0.64004(11) 0.0344(5) Uani 1 1 d . . . . .
H15 H 0.308127 0.762450 0.677161 0.041 Uiso 1 1 calc R . . . .
C5 C 0.40425(14) 0.57873(18) 0.72373(11) 0.0312(4) Uani 1 1 d . . . . .
H5 H 0.419407 0.658804 0.736501 0.037 Uiso 1 1 calc R . . . .
C3 C 0.38086(15) 0.37910(19) 0.76435(10) 0.0328(5) Uani 1 1 d . . . . .
C4 C 0.40202(15) 0.50188(19) 0.77972(11) 0.0346(5) Uani 1 1 d . . . . .
H4 H 0.414744 0.529405 0.830804 0.042 Uiso 1 1 calc R . . . .
C18 C 0.38839(16) 0.93680(19) 0.52905(12) 0.0391(5) Uani 1 1 d . . . . .
H18 H 0.407123 0.981450 0.490547 0.047 Uiso 1 1 calc R . . . .
C16 C 0.32652(17) 0.9281(2) 0.64119(13) 0.0421(5) Uani 1 1 d . . . . .
H16 H 0.302071 0.966854 0.679307 0.050 Uiso 1 1 calc R . . . .
C17 C 0.35811(17) 0.9936(2) 0.58662(13) 0.0443(5) Uani 1 1 d . . . . .
H17 H 0.358788 1.077021 0.589070 0.053 Uiso 1 1 calc R . . . .


_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 C13 1.369(2) . ?
O1 C1 1.371(2) . ?
O3 C11 1.334(2) . ?
O2 C3 1.261(2) . ?
O4 C20 1.225(2) . ?
C8 C13 1.399(3) . ?
C8 C7 1.438(2) . ?
C8 C9 1.413(3) . ?
C13 C12 1.381(3) . ?
C7 C6 1.388(3) . ?
C7 C14 1.474(3) . ?
C9 C20 1.479(3) . ?
C9 C10 1.377(3) . ?
C1 C6 1.444(3) . ?
C1 C2 1.354(3) . ?
C11 C12 1.398(3) . ?
C11 C10 1.403(3) . ?
C6 C5 1.448(2) . ?
C2 C3 1.431(3) . ?
C14 C19 1.413(3) . ?
C14 C15 1.403(3) . ?
C20 C19 1.483(3) . ?
C19 C18 1.394(3) . ?
C15 C16 1.388(3) . ?
C5 C4 1.346(3) . ?
C3 C4 1.440(3) . ?
C18 C17 1.378(3) . ?
C16 C17 1.393(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
C13 O1 C1 120.28(15) . . ?
C13 C8 C7 120.27(17) . . ?
C13 C8 C9 116.72(17) . . ?
C9 C8 C7 122.96(18) . . ?
O1 C13 C8 120.69(16) . . ?
O1 C13 C12 116.31(17) . . ?
C12 C13 C8 122.98(17) . . ?
C8 C7 C14 117.16(16) . . ?
C6 C7 C8 117.48(18) . . ?
C6 C7 C14 125.36(17) . . ?
C8 C9 C20 118.39(17) . . ?
C10 C9 C8 121.11(19) . . ?
C10 C9 C20 120.34(17) . . ?
O1 C1 C6 120.24(16) . . ?
C2 C1 O1 116.02(17) . . ?
C2 C1 C6 123.63(17) . . ?
O3 C11 C12 122.27(19) . . ?
O3 C11 C10 118.35(17) . . ?
C12 C11 C10 119.37(17) . . ?
C7 C6 C1 119.74(16) . . ?
C7 C6 C5 125.60(18) . . ?
C1 C6 C5 114.64(17) . . ?
C13 C12 C11 119.01(19) . . ?
C1 C2 C3 120.03(19) . . ?
C19 C14 C7 119.12(17) . . ?
C15 C14 C7 123.17(18) . . ?
C15 C14 C19 117.61(19) . . ?
O4 C20 C9 121.09(18) . . ?
O4 C20 C19 122.00(19) . . ?
C9 C20 C19 116.88(16) . . ?
C9 C10 C11 120.56(17) . . ?
C14 C19 C20 121.18(18) . . ?
C18 C19 C14 120.46(19) . . ?
C18 C19 C20 118.19(18) . . ?
C16 C15 C14 121.1(2) . . ?
C4 C5 C6 121.92(19) . . ?
O2 C3 C2 122.9(2) . . ?
O2 C3 C4 119.85(18) . . ?
C2 C3 C4 117.21(18) . . ?
C5 C4 C3 121.81(18) . . ?
C17 C18 C19 120.7(2) . . ?
C15 C16 C17 120.2(2) . . ?
C18 C17 C16 119.6(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 1.956
_oxdiff_exptl_absorpt_empirical_full_min 0.656
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_bx1-1
_database_code_depnum_ccdc_archive 'CCDC 2272293'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;University of Toyama
Japan
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-10-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Coerulein B sulfate'
_chemical_formula_moiety         'H O4 S, C20 H11 O4'
_chemical_formula_sum            'C20 H12 O8 S'
_chemical_formula_weight         412.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H12 O8 S'
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'
S S 0.3331 0.5567 '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                   8.1750(5)
_cell_length_b                   8.5487(4)
_cell_length_c                   13.2740(6)
_cell_angle_alpha                71.637(4)
_cell_angle_beta                 81.162(4)
_cell_angle_gamma                68.995(5)
_cell_volume                     821.05(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2633
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      67.5020
_cell_measurement_theta_min      3.5110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 -4 0.1084
1 0 8 0.0437
-1 1 -7 0.0306
-2 -5 1 0.0997
-3 0 6 0.0541
1 5 1 0.0639
3 -1 -6 0.0417
-5 1 2 0.0564
4 -1 -2 0.0380
1 5 5 0.0752
5 0 4 0.0541
0 0 8 0.0384
-2 -5 -5 0.1124
-5 0 -1 0.0536

_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.079
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.2043 -5.0188 -3.7489 -0.0079 -0.0430 0.9990
1.3134 -0.2977 7.7779 0.2339 0.9717 0.0345
-1.3266 0.7026 -7.4552 -0.2326 -0.9657 -0.1151
-2.0222 -5.0860 0.7253 -0.4234 0.4990 0.7561
-3.2896 -0.2185 5.8563 -0.6145 0.7190 -0.3247
1.1007 5.3959 1.1306 0.2547 -0.3019 -0.9187
3.0495 -0.8738 -6.0537 0.5597 -0.6541 0.5088
-4.5301 0.8223 1.5551 -0.8304 0.1084 -0.5466
4.3207 -1.2259 -1.7754 0.7879 -0.1027 0.6071
0.9371 5.1915 5.0043 0.2195 0.1843 -0.9580
4.5160 -0.0767 3.5651 0.8311 0.4516 0.3247
-0.3759 -0.1272 8.0610 -0.0769 0.9872 -0.1395
-2.3283 -5.3361 -4.7331 -0.4782 -0.1435 0.8664
-4.9252 -0.0021 -1.2641 -0.9092 -0.1671 -0.3814

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6625
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.027
_diffrn_reflns_theta_min         3.512
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  47.00   0.50    0.20    --   39.63  25.00  30.00   50
  2  ω     54.00  81.00   0.50    0.20    --   39.63  25.00  30.00   54
  3  ω     19.00 107.00   0.50    0.20    --   39.63  50.00 -90.00  176
  4  ω    -17.00  42.00   0.50    0.20    --   39.63 -50.00 -90.00  118
  5  ω     27.00  55.00   0.50    0.20    --   39.63 -63.00  30.00   56
  6  ω    -28.00  19.00   0.50    0.20    --   39.63 -37.00  60.00   94
  7  ω    -25.00  10.00   0.50    0.20    --   39.63 -37.00 120.00   70
  8  ω     14.00  40.00   0.50    0.20    --   39.63 -37.00 120.00   52
  9  ω    -27.00  23.00   0.50    0.20    --   39.63 -63.00  30.00  100
 10  ω     -5.00  20.00   0.50    0.20    --   39.63 -12.00 -90.00   50
 11  ω     53.00  93.00   0.50    0.43    --   96.37 -77.00-150.00   80
 12  ω     77.00 102.00   0.50    0.43    --   96.37 -77.00-120.00   50
 13  ω     30.00  57.00   0.50    0.43    --   96.37 -50.00-120.00   54
 14  ω     31.00  57.00   0.50    0.43    --   96.37 -50.00-180.00   52
 15  ω     30.00  57.00   0.50    0.43    --   96.37 -50.00-150.00   54
 16  ω     29.00  55.00   0.50    0.43    --   96.37 -50.00 -90.00   52
 17  ω     32.00  57.00   0.50    0.43    --   96.37 -50.00  30.00   50
 18  ω     29.00  54.00   0.50    0.43    --   96.37 -50.00   0.00   50
 19  ω     30.00  56.00   0.50    0.43    --   96.37 -50.00  60.00   52
 20  ω     29.00  54.00   0.50    0.43    --   96.37 -50.00  90.00   50
 21  ω     32.00  68.00   0.50    0.43    --   96.37 -59.00 120.00   72
 22  ω     35.00  87.00   0.50    0.20    --   39.63-118.00  47.00  104
 23  ω     43.00  69.00   0.50    0.20    --   39.63-138.00  30.00   52
 24  ω     42.00 100.00   0.50    0.20    --   39.63-138.00 -30.00  116
 25  ω     76.00 101.00   0.50    0.20    --   39.63-157.00-107.00   50
 26  ω     67.00 127.00   0.50    0.43    --   96.37 -86.00  30.00  120
 27  ω     30.00 109.00   0.50    0.43    --   96.37-117.00  90.00  158
 28  ω     56.00 102.00   0.50    0.43    --   96.37-118.00  47.00   92
 29  ω     25.00  64.00   0.50    0.43    --   96.37 -86.00  30.00   78
 30  ω     62.00 108.00   0.50    0.43    --   96.37-117.00 -60.00   92
 31  ω     28.00 102.00   0.50    0.43    --   96.37-117.00-120.00  148
 32  ω     73.00 108.00   0.50    0.43    --   96.37-117.00-180.00   70
 33  ω    133.00 167.00   0.50    0.43    --   96.37  25.00 -30.00   68
 34  ω     90.00 152.00   0.50    0.43    --   96.37  42.00 -90.00  124
 35  ω     81.00 121.00   0.50    0.43    --   96.37  42.00-120.00   80
 36  ω     80.00 163.00   0.50    0.43    --   96.37  50.00-180.00  166
 37  ω    128.00 153.00   0.50    0.43    --   96.37  33.00-150.00   50
 38  ω    139.00 164.00   0.50    0.43    --   96.37  42.00-120.00   50
 39  ω     79.00 127.00   0.50    0.43    --   96.37  25.00 -30.00   96
 40  ω     84.00 123.00   0.50    0.43    --   96.37  96.00  90.00   78
 41  ω     97.00 122.00   0.50    0.43    --   96.37 118.00 133.00   50
 42  ω    137.00 169.00   0.50    0.43    --   96.37  96.00  90.00   64
 43  ω     54.00  80.00   0.50    0.20    --   39.63 157.00 -72.00   52
 44  ω     82.00 107.00   0.50    0.43    --   96.37 157.00 -72.00   50
 45  ω    -12.00  33.00   0.50    0.20    --  -39.95  12.00  90.00   90
 46  ω    -80.00 -46.00   0.50    0.43    --  -96.68  68.00 120.00   68
 47  ω    -68.00 -43.00   0.50    0.43    --  -96.68  59.00 -30.00   50
 48  ω    -10.00  16.00   0.50    0.20    --  -39.95  25.00-180.00   52
 49  ω    -88.00 -22.00   0.50    0.43    --  -96.68  96.00 -30.00  132
 50  ω    -70.00 -45.00   0.50    0.20    --  -39.95 157.00 -72.00   50
 51  ω    -51.00 -25.00   0.50    0.20    --  -39.95 118.00 133.00   52
 52  ω    -87.00 -48.00   0.50    0.43    --  -96.68 118.00 133.00   78
 53  ω    -55.00 -24.00   0.50    0.20    --  -39.95 -37.00  60.00   62
 54  ω    -89.00 -64.00   0.50    0.20    --  -39.95 -37.00  60.00   50
 55  ω   -163.00 -83.00   0.50    0.43    --  -96.68 -33.00  60.00  160
 56  ω   -145.00-120.00   0.50    0.43    --  -96.68-118.00  47.00   50
 57  ω   -150.00 -82.00   0.50    0.43    --  -96.68 -86.00   0.00  136
 58  ω   -103.00 -77.00   0.50    0.43    --  -96.68-157.00-107.00   52
 59  ω    -99.00 -74.00   0.50    0.20    --  -39.95-157.00-107.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1847931000
_diffrn_orient_matrix_UB_12      0.0096662000
_diffrn_orient_matrix_UB_13      -0.0007654000
_diffrn_orient_matrix_UB_21      0.0028323000
_diffrn_orient_matrix_UB_22      -0.0819410000
_diffrn_orient_matrix_UB_23      0.1213098000
_diffrn_orient_matrix_UB_31      0.0817185000
_diffrn_orient_matrix_UB_32      -0.1834937000
_diffrn_orient_matrix_UB_33      -0.0163886000
_diffrn_oxdiff_digest_frames     
;
01d012548447f445b84ceabe5470c7181c045766644
;
_diffrn_oxdiff_digest_hkl        
;
0186125661a377d31bbad4e7980df5c6648853
;
_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                2607
_reflns_number_total             2968
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.048
_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)+(0.1351P)²+0.0426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1765
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C12(H12), C10(H10), C4(H4), C15(H15), C18(H18), C16(H16),
 C17(H17)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O6(H6)
;
_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
S1 S -0.00018(8) 1.35301(7) 0.89669(4) 0.0322(2) Uani 1 1 d . . . . .
O1 O 0.1284(2) 0.7807(2) 0.65214(14) 0.0330(4) Uani 1 1 d . . . . .
O2 O 0.3086(3) 0.9035(2) 0.93051(15) 0.0391(5) Uani 1 1 d . . . . .
H2 H 0.214822 0.988424 0.918707 0.059 Uiso 1 1 calc GR . . . .
O8 O -0.0200(3) 1.4606(2) 0.78720(14) 0.0405(5) Uani 1 1 d . . . . .
O4 O 0.5018(3) 0.1923(2) 0.46145(15) 0.0387(5) Uani 1 1 d . . . . .
O7 O -0.1384(2) 1.4293(2) 0.96756(15) 0.0401(5) Uani 1 1 d . . . . .
O3 O -0.0289(3) 0.7380(2) 0.34169(15) 0.0393(5) Uani 1 1 d . . . . .
H3 H 0.004139 0.676647 0.299107 0.059 Uiso 1 1 calc GR . . . .
O6 O 0.1760(2) 1.3441(2) 0.93261(15) 0.0390(5) Uani 1 1 d . . . . .
H6 H 0.155898 1.413201 0.969635 0.058 Uiso 1 1 calc GR . . . .
O5 O 0.0175(3) 1.1744(2) 0.90693(16) 0.0415(5) Uani 1 1 d . . . . .
C6 C 0.3838(3) 0.5682(3) 0.74792(19) 0.0314(5) Uani 1 1 d . . . . .
C8 C 0.2886(3) 0.5201(3) 0.6003(2) 0.0316(6) Uani 1 1 d . . . . .
C9 C 0.3136(3) 0.4317(3) 0.5221(2) 0.0315(5) Uani 1 1 d . . . . .
C1 C 0.2421(3) 0.7310(3) 0.7295(2) 0.0320(6) Uani 1 1 d . . . . .
C7 C 0.3932(3) 0.4525(3) 0.6901(2) 0.0315(5) Uani 1 1 d . . . . .
C2 C 0.2098(3) 0.8449(3) 0.7901(2) 0.0334(6) Uani 1 1 d . . . . .
H2A H 0.109749 0.947620 0.779221 0.040 Uiso 1 1 calc R . . . .
C5 C 0.5056(3) 0.5416(3) 0.8229(2) 0.0339(6) Uani 1 1 d . . . . .
H5 H 0.607445 0.440602 0.833485 0.041 Uiso 1 1 calc R . . . .
C13 C 0.1571(3) 0.6854(3) 0.5830(2) 0.0324(6) Uani 1 1 d . . . . .
C11 C 0.0772(3) 0.6665(3) 0.4224(2) 0.0350(6) Uani 1 1 d . . . . .
C14 C 0.5060(3) 0.2676(3) 0.7159(2) 0.0322(6) Uani 1 1 d . . . . .
C3 C 0.3259(3) 0.8065(3) 0.8671(2) 0.0332(6) Uani 1 1 d . . . . .
C12 C 0.0502(3) 0.7564(3) 0.4973(2) 0.0341(6) Uani 1 1 d . . . . .
H12 H -0.040731 0.865788 0.489823 0.041 Uiso 1 1 calc R . . . .
C10 C 0.2130(3) 0.5037(3) 0.4344(2) 0.0333(6) Uani 1 1 d . . . . .
H10 H 0.234848 0.444044 0.381673 0.040 Uiso 1 1 calc R . . . .
C4 C 0.4800(3) 0.6560(3) 0.8792(2) 0.0336(6) Uani 1 1 d . . . . .
H4 H 0.565096 0.636131 0.927224 0.040 Uiso 1 1 calc R . . . .
C15 C 0.5709(4) 0.1737(3) 0.8169(2) 0.0364(6) Uani 1 1 d . . . . .
H15 H 0.539838 0.228144 0.872622 0.044 Uiso 1 1 calc R . . . .
C19 C 0.5417(3) 0.1786(3) 0.6378(2) 0.0340(6) Uani 1 1 d . . . . .
C20 C 0.4581(3) 0.2605(3) 0.5340(2) 0.0330(6) Uani 1 1 d . . . . .
C18 C 0.6515(4) 0.0044(3) 0.6592(2) 0.0368(6) Uani 1 1 d . . . . .
H18 H 0.677631 -0.054219 0.605655 0.044 Uiso 1 1 calc R . . . .
C16 C 0.6812(4) 0.0000(3) 0.8362(2) 0.0409(6) Uani 1 1 d . . . . .
H16 H 0.728061 -0.061213 0.904256 0.049 Uiso 1 1 calc R . . . .
C17 C 0.7225(4) -0.0832(3) 0.7581(2) 0.0382(6) Uani 1 1 d . . . . .
H17 H 0.799578 -0.200416 0.771707 0.046 Uiso 1 1 calc R . . . .


_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
S1 O8 1.4518(18) . ?
S1 O7 1.4556(19) . ?
S1 O6 1.555(2) . ?
S1 O5 1.4451(19) . ?
O1 C1 1.354(3) . ?
O1 C13 1.353(3) . ?
O2 C3 1.318(3) . ?
O4 C20 1.221(3) . ?
O3 C11 1.329(3) . ?
C6 C1 1.434(3) . ?
C6 C7 1.407(4) . ?
C6 C5 1.425(4) . ?
C8 C9 1.418(4) . ?
C8 C7 1.418(4) . ?
C8 C13 1.410(3) . ?
C9 C10 1.374(4) . ?
C9 C20 1.495(3) . ?
C1 C2 1.382(4) . ?
C7 C14 1.475(3) . ?
C2 C3 1.384(4) . ?
C5 C4 1.352(4) . ?
C13 C12 1.384(4) . ?
C11 C12 1.385(4) . ?
C11 C10 1.415(3) . ?
C14 C15 1.400(4) . ?
C14 C19 1.409(4) . ?
C3 C4 1.428(3) . ?
C15 C16 1.398(4) . ?
C19 C20 1.482(4) . ?
C19 C18 1.399(3) . ?
C18 C17 1.388(4) . ?
C16 C17 1.370(4) . ?

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
O8 S1 O7 112.01(11) . . ?
O8 S1 O6 107.46(12) . . ?
O7 S1 O6 106.96(11) . . ?
O5 S1 O8 112.01(12) . . ?
O5 S1 O7 112.54(12) . . ?
O5 S1 O6 105.36(11) . . ?
C13 O1 C1 120.17(19) . . ?
C7 C6 C1 118.3(2) . . ?
C7 C6 C5 126.1(2) . . ?
C5 C6 C1 115.6(2) . . ?
C9 C8 C7 123.0(2) . . ?
C13 C8 C9 116.6(2) . . ?
C13 C8 C7 120.3(2) . . ?
C8 C9 C20 118.6(2) . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 C20 120.0(2) . . ?
O1 C1 C6 121.5(2) . . ?
O1 C1 C2 115.7(2) . . ?
C2 C1 C6 122.8(2) . . ?
C6 C7 C8 117.3(2) . . ?
C6 C7 C14 124.4(2) . . ?
C8 C7 C14 118.3(2) . . ?
C1 C2 C3 118.8(2) . . ?
C4 C5 C6 121.8(2) . . ?
O1 C13 C8 120.4(2) . . ?
O1 C13 C12 117.0(2) . . ?
C12 C13 C8 122.6(2) . . ?
O3 C11 C12 117.7(2) . . ?
O3 C11 C10 122.5(2) . . ?
C12 C11 C10 119.8(2) . . ?
C15 C14 C7 122.7(2) . . ?
C15 C14 C19 118.3(2) . . ?
C19 C14 C7 118.9(2) . . ?
O2 C3 C2 124.5(2) . . ?
O2 C3 C4 115.5(2) . . ?
C2 C3 C4 120.0(2) . . ?
C13 C12 C11 119.4(2) . . ?
C9 C10 C11 120.1(2) . . ?
C5 C4 C3 120.4(2) . . ?
C16 C15 C14 120.2(2) . . ?
C14 C19 C20 121.9(2) . . ?
C18 C19 C14 120.1(2) . . ?
C18 C19 C20 117.8(2) . . ?
O4 C20 C9 120.9(2) . . ?
O4 C20 C19 122.5(2) . . ?
C19 C20 C9 116.6(2) . . ?
C17 C18 C19 120.4(2) . . ?
C17 C16 C15 120.9(3) . . ?
C16 C17 C18 119.8(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 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.768
####################################################################### 
# 
# 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_exp_29
_database_code_depnum_ccdc_archive 'CCDC 2308442'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;University of Toyama
Japan
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-12-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        CB-OTf
_chemical_formula_moiety         '2(C21 H9 F3 O6 S)'
_chemical_formula_sum            'C42 H18 F6 O12 S2'
_chemical_formula_weight         892.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C42 H18 F6 O12 S2 '
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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 '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                   5.78110(10)
_cell_length_b                   12.0613(4)
_cell_length_c                   12.5328(3)
_cell_angle_alpha                100.454(2)
_cell_angle_beta                 90.274(2)
_cell_angle_gamma                98.211(2)
_cell_volume                     850.14(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5663
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.2320
_cell_measurement_theta_min      3.5420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.395
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.298
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -1 1 0.4493
0 7 -5 0.0768
-4 0 0 0.3926
0 -7 5 0.0694
4 -1 1 0.4493
0 7 1 0.0843
-4 1 -1 0.3838
0 -7 -1 0.0712
0 -4 -6 0.0339
0 4 6 0.0583
0 0 8 0.0320
0 0 -8 0.0132
0 0 -8 0.0188

_exptl_crystal_size_max          0.797
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.7231 -1.2416 0.9791 0.0016 -0.0040 1.0000
0.0173 7.0822 -4.6021 0.2334 0.9707 -0.0577
-3.7205 0.2386 -0.3271 -0.0346 -0.1332 -0.9905
0.0024 -7.0863 4.6057 -0.2333 -0.9704 0.0629
3.7230 -1.1368 0.9693 -0.0020 0.0091 1.0000
-0.0522 7.3715 1.0911 -0.4766 0.8790 0.0133
-3.7245 1.2450 -0.9535 -0.0049 0.0038 -1.0000
0.0369 -7.3661 -1.0949 0.4766 -0.8790 -0.0174
0.0033 -3.8157 -6.2233 0.9375 -0.3328 -0.1016
-0.0564 3.8378 6.2179 -0.9388 0.3332 0.0875
-0.0644 -0.0253 8.0042 -0.9776 -0.1804 0.1080
-0.0286 0.0548 -8.0045 0.9747 0.1798 -0.1326
0.1298 0.0044 -8.0010 0.9793 0.1808 -0.0906

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7226
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.300
_diffrn_reflns_theta_min         3.588
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  -1.00   0.50    0.30    --  -41.44  21.00  30.00   54
  2  ω    -55.00 -29.00   0.50    1.18    --  -95.43  50.00  30.00   52
  3  ω    -56.00 -29.00   0.50    1.18    --  -95.43  50.00   0.00   54
  4  ω    -66.00 -27.00   0.50    1.18    --  -95.43  59.00  60.00   78
  5  ω    -54.00 -27.00   0.50    1.18    --  -95.43  59.00  90.00   54
  6  ω    -57.00 -32.00   0.50    1.18    --  -95.43  50.00  90.00   50
  7  ω    -70.00 -44.00   0.50    0.30    --  -41.44 119.00  52.00   52
  8  ω    -99.00 -67.00   0.50    1.18    --  -95.43 119.00  52.00   64
  9  ω    -92.00 -28.00   0.50    1.18    --  -95.43 117.00 -60.00  128
 10  ω    -81.00 -56.00   0.50    1.18    --  -95.43 156.00-151.00   50
 11  ω    -97.00 -48.00   0.50    1.18    --  -95.43  96.00 -60.00   98
 12  ω    -57.00 -32.00   0.50    1.18    --  -95.43  50.00 -90.00   50
 13  ω    -22.00  34.00   0.50    0.30    --  -41.44  11.00-120.00  112
 14  ω     80.00 113.00   0.50    0.30    --   41.75  21.00 -60.00   66
 15  ω     72.00  98.00   0.50    0.30    --   41.75  32.00 -90.00   52
 16  ω     74.00 119.00   0.50    1.18    --   95.75  59.00 -30.00   90
 17  ω    127.00 164.00   0.50    1.18    --   95.75  59.00 -30.00   74
 18  ω    138.00 163.00   0.50    1.18    --   95.75 117.00 -90.00   50
 19  ω    107.00 134.00   0.50    1.18    --   95.75 119.00  52.00   54
 20  ω     79.00 108.00   0.50    0.30    --   41.75 138.00   0.00   58
 21  ω     67.00 108.00   0.50    0.30    --   41.75 138.00 -90.00   82
 22  ω     64.00  96.00   0.50    0.30    --   41.75 156.00-151.00   64
 23  ω     91.00 133.00   0.50    1.18    --   95.75 117.00 -90.00   84
 24  ω     29.00  65.00   0.50    0.30    --   41.75  32.00 -90.00   72
 25  ω     26.00  52.00   0.50    0.30    --   41.75  21.00 -60.00   52
 26  ω     31.00  57.00   0.50    1.18    --   95.75 -50.00-150.00   52
 27  ω     51.00 106.00   0.50    1.18    --   95.75 -77.00-180.00  110
 28  ω     85.00 110.00   0.50    1.18    --   95.75-117.00-120.00   50
 29  ω     65.00  94.00   0.50    1.18    --   95.75-117.00-150.00   58
 30  ω     41.00  68.00   0.50    1.18    --   95.75 -59.00-120.00   54
 31  ω     29.00  54.00   0.50    1.18    --   95.75 -50.00-180.00   50
 32  ω     30.00  67.00   0.50    1.18    --   95.75 -59.00-180.00   74
 33  ω     34.00  60.00   0.50    1.18    --   95.75-117.00-150.00   52
 34  ω     24.00  49.00   0.50    0.30    --   41.75-119.00 -32.00   50
 35  ω     48.00  73.00   0.50    1.18    --   95.75-119.00 -32.00   50
 36  ω     63.00  92.00   0.50    1.18    --   95.75 -77.00 -30.00   58
 37  ω     33.00  65.00   0.50    1.18    --   95.75 -59.00  30.00   64
 38  ω     31.00 106.00   0.50    1.18    --   95.75 -77.00   0.00  150
 39  ω     39.00  99.00   0.50    1.18    --   95.75-117.00 150.00  120
 40  ω     57.00  82.00   0.50    1.18    --   95.75-156.00 171.00   50
 41  ω     58.00 107.00   0.50    0.30    --   41.75-156.00 171.00   98
 42  ω     29.00  54.00   0.50    1.18    --   95.75 -50.00 120.00   50
 43  ω     29.00  83.00   0.50    1.18    --   95.75 -68.00 120.00  108
 44  ω     -9.00  35.00   0.50    0.30    --   41.75 -54.00   0.00   88
 45  ω    -25.00  14.00   0.50    0.30    --   41.75 -32.00  60.00   78
 46  ω    -88.00 -60.00   0.50    0.30    --  -41.44-156.00 171.00   56
 47  ω    -81.00 -18.00   0.50    0.30    --  -41.44 -77.00-180.00  126
 48  ω    -99.00 -67.00   0.50    0.30    --  -41.44-138.00-150.00   64
 49  ω   -109.00 -84.00   0.50    0.30    --  -41.44-138.00 -90.00   50
 50  ω   -124.00 -99.00   0.50    1.18    --  -95.43-119.00 -32.00   50
 51  ω   -137.00 -76.00   0.50    1.18    --  -95.43 -50.00  60.00  122
 52  ω   -162.00 -91.00   0.50    1.18    --  -95.43 -42.00   0.00  142
 53  ω   -149.00 -83.00   0.50    1.18    --  -95.43 -42.00 -90.00  132
 54  ω   -128.00 -83.00   0.50    1.18    --  -95.43 -25.00-180.00   90
 55  ω   -160.00 -81.00   0.50    1.18    --  -95.43 -50.00-120.00  158
 56  ω   -142.00 -78.00   0.50    1.18    --  -95.43 -86.00 -30.00  128
 57  ω    -94.00 -68.00   0.50    0.30    --  -41.44 156.00-151.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0170666000
_diffrn_orient_matrix_UB_12      -0.0464582000
_diffrn_orient_matrix_UB_13      -0.1221514000
_diffrn_orient_matrix_UB_21      0.0455981000
_diffrn_orient_matrix_UB_22      0.1227905000
_diffrn_orient_matrix_UB_23      -0.0217846000
_diffrn_orient_matrix_UB_31      0.2649392000
_diffrn_orient_matrix_UB_32      0.0013639000
_diffrn_orient_matrix_UB_33      0.0156275000
_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                2865
_reflns_number_total             3076
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.2755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C2(H2), C15(H15), C5(H5), C10(H10), C4(H4), C18(H18), C17(H17),
 C16(H16)
;
_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
S1 S 0.20913(6) 0.23045(3) 0.05312(3) 0.01824(13) Uani 1 1 d . . . . .
F2 F 0.54881(16) 0.14267(9) 0.12889(8) 0.0282(2) Uani 1 1 d . . . . .
F1 F 0.66208(16) 0.28547(9) 0.05119(9) 0.0342(3) Uani 1 1 d . . . . .
F3 F 0.52476(18) 0.12237(9) -0.04546(8) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.67858(17) 0.38811(9) 0.48079(8) 0.0186(2) Uani 1 1 d . . . . .
O3 O 0.23131(18) 0.32719(9) 0.15646(8) 0.0193(2) Uani 1 1 d . . . . .
O6 O 0.17848(19) 0.28478(10) -0.03548(9) 0.0254(3) Uani 1 1 d . . . . .
O4 O -0.29205(17) 0.13141(9) 0.41538(9) 0.0214(2) Uani 1 1 d . . . . .
O2 O 1.14500(18) 0.49529(10) 0.79702(9) 0.0237(3) Uani 1 1 d . . . . .
O5 O 0.06102(19) 0.13140(10) 0.06978(9) 0.0243(3) Uani 1 1 d . . . . .
C19 C -0.0581(3) 0.13951(13) 0.57304(12) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.5212(2) 0.32814(12) 0.64669(12) 0.0170(3) Uani 1 1 d . . . . .
C8 C 0.2985(2) 0.27472(12) 0.47581(12) 0.0165(3) Uani 1 1 d . . . . .
C7 C 0.3318(2) 0.26158(13) 0.58790(12) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.7051(3) 0.38730(12) 0.58957(12) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.0914(3) 0.22968(12) 0.41469(12) 0.0174(3) Uani 1 1 d . . . . .
C12 C 0.4560(3) 0.35240(13) 0.31976(12) 0.0182(3) Uani 1 1 d . . . . .
H12 H 0.579562 0.393652 0.286933 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4746(2) 0.33801(12) 0.42625(12) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.9117(2) 0.43978(13) 0.63714(12) 0.0185(3) Uani 1 1 d . . . . .
H2 H 1.029181 0.472077 0.594492 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2498(3) 0.30409(13) 0.26327(12) 0.0179(3) Uani 1 1 d . . . . .
C14 C 0.1590(2) 0.17918(12) 0.62961(12) 0.0170(3) Uani 1 1 d . . . . .
C20 C -0.1049(2) 0.16494(12) 0.46432(12) 0.0173(3) Uani 1 1 d . . . . .
C15 C 0.2041(3) 0.13303(13) 0.72132(12) 0.0197(3) Uani 1 1 d . . . . .
H15 H 0.354409 0.151906 0.756232 0.024 Uiso 1 1 calc R U . . .
C3 C 0.9567(3) 0.44756(13) 0.75203(13) 0.0189(3) Uani 1 1 d . . . . .
C5 C 0.5595(3) 0.34739(13) 0.76367(12) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.436844 0.320247 0.806732 0.023 Uiso 1 1 calc R U . . .
C10 C 0.0635(3) 0.24538(13) 0.30815(12) 0.0180(3) Uani 1 1 d . . . . .
H10 H -0.078646 0.216710 0.267773 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7607(3) 0.40189(13) 0.81343(13) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.776995 0.411191 0.890127 0.025 Uiso 1 1 calc R U . . .
C18 C -0.2298(3) 0.06705(13) 0.61548(13) 0.0199(3) Uani 1 1 d . . . . .
H18 H -0.377148 0.043129 0.578413 0.024 Uiso 1 1 calc R U . . .
C17 C -0.1872(3) 0.02990(13) 0.71075(13) 0.0221(3) Uani 1 1 d . . . . .
H17 H -0.307307 -0.016052 0.741043 0.026 Uiso 1 1 calc R U . . .
C16 C 0.0325(3) 0.06017(13) 0.76201(13) 0.0220(3) Uani 1 1 d . . . . .
H16 H 0.065572 0.030983 0.825009 0.026 Uiso 1 1 calc R U . . .
C21 C 0.5078(3) 0.19349(14) 0.04706(13) 0.0226(3) 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
S1 O3 1.5693(11) . ?
S1 O6 1.4103(12) . ?
S1 O5 1.4156(11) . ?
S1 C21 1.8424(16) . ?
F2 C21 1.3233(19) . ?
F1 C21 1.3134(19) . ?
F3 C21 1.3245(19) . ?
O1 C1 1.3731(18) . ?
O1 C13 1.3646(18) . ?
O3 C11 1.4224(18) . ?
O4 C20 1.2201(18) . ?
O2 C3 1.2376(19) . ?
C19 C14 1.416(2) . ?
C19 C20 1.482(2) . ?
C19 C18 1.399(2) . ?
C6 C7 1.383(2) . ?
C6 C1 1.459(2) . ?
C6 C5 1.453(2) . ?
C8 C7 1.457(2) . ?
C8 C9 1.404(2) . ?
C8 C13 1.400(2) . ?
C7 C14 1.473(2) . ?
C1 C2 1.350(2) . ?
C9 C20 1.488(2) . ?
C9 C10 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(2) . ?
C12 C11 1.381(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.446(2) . ?
C11 C10 1.382(2) . ?
C14 C15 1.403(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(2) . ?
C3 C4 1.471(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.342(2) . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.382(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.391(2) . ?
C16 H16 0.9500 . ?

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
O3 S1 C21 101.30(7) . . ?
O6 S1 O3 105.62(6) . . ?
O6 S1 O5 122.85(7) . . ?
O6 S1 C21 106.97(7) . . ?
O5 S1 O3 111.86(6) . . ?
O5 S1 C21 106.10(7) . . ?
C13 O1 C1 120.07(11) . . ?
C11 O3 S1 122.22(9) . . ?
C14 C19 C20 121.87(13) . . ?
C18 C19 C14 120.18(14) . . ?
C18 C19 C20 117.78(13) . . ?
C7 C6 C1 119.22(13) . . ?
C7 C6 C5 126.45(13) . . ?
C5 C6 C1 114.33(13) . . ?
C9 C8 C7 122.79(13) . . ?
C13 C8 C7 119.82(13) . . ?
C13 C8 C9 117.36(14) . . ?
C6 C7 C8 117.48(13) . . ?
C6 C7 C14 125.37(14) . . ?
C8 C7 C14 117.14(13) . . ?
O1 C1 C6 120.55(13) . . ?
C2 C1 O1 116.05(13) . . ?
C2 C1 C6 123.35(14) . . ?
C8 C9 C20 119.78(13) . . ?
C10 C9 C8 121.39(13) . . ?
C10 C9 C20 118.83(13) . . ?
C13 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
C11 C12 C13 116.97(13) . . ?
O1 C13 C8 121.35(13) . . ?
O1 C13 C12 115.81(13) . . ?
C12 C13 C8 122.83(13) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.98(13) . . ?
C3 C2 H2 119.5 . . ?
C12 C11 O3 115.24(13) . . ?
C12 C11 C10 123.61(14) . . ?
C10 C11 O3 120.92(13) . . ?
C19 C14 C7 119.60(13) . . ?
C15 C14 C19 117.64(13) . . ?
C15 C14 C7 122.68(13) . . ?
O4 C20 C19 122.16(13) . . ?
O4 C20 C9 120.97(14) . . ?
C19 C20 C9 116.81(12) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.18(14) . . ?
C16 C15 H15 119.4 . . ?
O2 C3 C2 121.88(13) . . ?
O2 C3 C4 121.94(14) . . ?
C2 C3 C4 116.07(13) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 C6 122.76(14) . . ?
C4 C5 H5 118.6 . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.73(13) . . ?
C11 C10 H10 121.1 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.56(14) . . ?
C5 C4 H4 119.2 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 C19 120.71(14) . . ?
C17 C18 H18 119.6 . . ?
C18 C17 H17 120.2 . . ?
C18 C17 C16 119.61(14) . . ?
C16 C17 H17 120.2 . . ?
C15 C16 C17 120.21(14) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
F2 C21 S1 110.08(10) . . ?
F2 C21 F3 109.01(13) . . ?
F1 C21 S1 110.42(11) . . ?
F1 C21 F2 109.50(13) . . ?
F1 C21 F3 109.62(13) . . ?
F3 C21 S1 108.18(11) . . ?

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
S1 O3 C11 C12 117.02(13) . . . . ?
S1 O3 C11 C10 -68.22(16) . . . . ?
O1 C1 C2 C3 177.98(13) . . . . ?
O3 S1 C21 F2 69.18(12) . . . . ?
O3 S1 C21 F1 -51.83(12) . . . . ?
O3 S1 C21 F3 -171.79(10) . . . . ?
O3 C11 C10 C9 -177.60(13) . . . . ?
O6 S1 O3 C11 175.99(10) . . . . ?
O6 S1 C21 F2 179.55(10) . . . . ?
O6 S1 C21 F1 58.53(13) . . . . ?
O6 S1 C21 F3 -61.43(13) . . . . ?
O2 C3 C4 C5 -178.08(15) . . . . ?
O5 S1 O3 C11 40.02(12) . . . . ?
O5 S1 C21 F2 -47.74(13) . . . . ?
O5 S1 C21 F1 -168.75(11) . . . . ?
O5 S1 C21 F3 71.28(12) . . . . ?
C19 C14 C15 C16 -6.7(2) . . . . ?
C19 C18 C17 C16 -3.3(2) . . . . ?
C6 C7 C14 C19 162.94(14) . . . . ?
C6 C7 C14 C15 -20.3(2) . . . . ?
C6 C1 C2 C3 -4.6(2) . . . . ?
C6 C5 C4 C3 0.9(2) . . . . ?
C8 C7 C14 C19 -16.4(2) . . . . ?
C8 C7 C14 C15 160.40(14) . . . . ?
C8 C9 C20 O4 175.16(14) . . . . ?
C8 C9 C20 C19 -7.3(2) . . . . ?
C8 C9 C10 C11 1.9(2) . . . . ?
C7 C6 C1 O1 7.6(2) . . . . ?
C7 C6 C1 C2 -169.70(14) . . . . ?
C7 C6 C5 C4 171.72(15) . . . . ?
C7 C8 C9 C20 -0.3(2) . . . . ?
C7 C8 C9 C10 178.90(13) . . . . ?
C7 C8 C13 O1 0.1(2) . . . . ?
C7 C8 C13 C12 178.97(14) . . . . ?
C7 C14 C15 C16 176.47(14) . . . . ?
C1 O1 C13 C8 -6.8(2) . . . . ?
C1 O1 C13 C12 174.17(12) . . . . ?
C1 C6 C7 C8 -13.9(2) . . . . ?
C1 C6 C7 C14 166.82(13) . . . . ?
C1 C6 C5 C4 -8.7(2) . . . . ?
C1 C2 C3 O2 179.97(14) . . . . ?
C1 C2 C3 C4 -3.7(2) . . . . ?
C9 C8 C7 C6 -167.20(13) . . . . ?
C9 C8 C7 C14 12.2(2) . . . . ?
C9 C8 C13 O1 177.81(13) . . . . ?
C9 C8 C13 C12 -3.3(2) . . . . ?
C12 C11 C10 C9 -3.3(2) . . . . ?
C13 O1 C1 C6 3.1(2) . . . . ?
C13 O1 C1 C2 -179.38(13) . . . . ?
C13 C8 C7 C6 10.4(2) . . . . ?
C13 C8 C7 C14 -170.21(13) . . . . ?
C13 C8 C9 C20 -177.98(13) . . . . ?
C13 C8 C9 C10 1.2(2) . . . . ?
C13 C12 C11 O3 175.98(12) . . . . ?
C13 C12 C11 C10 1.4(2) . . . . ?
C2 C3 C4 C5 5.6(2) . . . . ?
C11 C12 C13 O1 -178.99(12) . . . . ?
C11 C12 C13 C8 2.0(2) . . . . ?
C14 C19 C20 O4 -179.66(14) . . . . ?
C14 C19 C20 C9 2.9(2) . . . . ?
C14 C19 C18 C17 -2.4(2) . . . . ?
C14 C15 C16 C17 1.2(2) . . . . ?
C20 C19 C14 C7 9.1(2) . . . . ?
C20 C19 C14 C15 -167.82(13) . . . . ?
C20 C19 C18 C17 172.88(13) . . . . ?
C20 C9 C10 C11 -178.91(13) . . . . ?
C5 C6 C7 C8 165.71(14) . . . . ?
C5 C6 C7 C14 -13.6(2) . . . . ?
C5 C6 C1 O1 -172.06(13) . . . . ?
C5 C6 C1 C2 10.7(2) . . . . ?
C10 C9 C20 O4 -4.1(2) . . . . ?
C10 C9 C20 C19 173.46(13) . . . . ?
C18 C19 C14 C7 -175.82(13) . . . . ?
C18 C19 C14 C15 7.2(2) . . . . ?
C18 C19 C20 O4 5.2(2) . . . . ?
C18 C19 C20 C9 -172.32(13) . . . . ?
C18 C17 C16 C15 3.9(2) . . . . ?
C21 S1 O3 C11 -72.62(11) . . . . ?

_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.806
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/Et2O'
