# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_dhbd
_audit_block_doi                 10.5517/ccdc.csd.cc27617r
_database_code_depnum_ccdc_archive 'CCDC 2061383'
loop_
_audit_author_name
_audit_author_address
'Konrad Dyk'
;University of Maria Curie Sklodowska in Lublin
Poland
;
_audit_update_record             
;
2021-02-17 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
konrad.dyk@poczta.umcs.lublin.pl
_chemical_name_common            BHDB
_chemical_name_systematic        
5,5?-bis(4-hydroxyphenyl)-2,2?-dihydroxy-1,1?-biphenyl
_chemical_formula_moiety         'C24 H18 O4, 2[H2O]'
_chemical_formula_sum            'C24 H18 O4'
_chemical_formula_weight         370.38
_chemical_melting_point          523
_chemical_oxdiff_usercomment     '0.2 x 0.2 x 0'
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      cubic
_space_group_IT_number           228
_space_group_name_H-M_alt        'F d -3 c'
_space_group_name_Hall           '-F 4cvw 2vw 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+3/4, z+1/2'
'-x+3/4, y+1/2, -z+1/4'
'x+1/2, -y+1/4, -z+3/4'
'z, x, y'
'z+1/2, -x+1/4, -y+3/4'
'-z+1/4, -x+3/4, y+1/2'
'-z+3/4, x+1/2, -y+1/4'
'y, z, x'
'-y+3/4, z+1/2, -x+1/4'
'y+1/2, -z+1/4, -x+3/4'
'-y+1/4, -z+3/4, x+1/2'
'y+3/4, x+1/4, -z'
'-y+1/2, -x+1/2, -z+1/2'
'y+1/4, -x, z+3/4'
'-y, x+3/4, z+1/4'
'x+3/4, z+1/4, -y'
'-x, z+3/4, y+1/4'
'-x+1/2, -z+1/2, -y+1/2'
'x+1/4, -z, y+3/4'
'z+3/4, y+1/4, -x'
'z+1/4, -y, x+3/4'
'-z, y+3/4, x+1/4'
'-z+1/2, -y+1/2, -x+1/2'
'x, y+1/2, z+1/2'
'-x+1/4, -y+5/4, z+1'
'-x+3/4, y+1, -z+3/4'
'x+1/2, -y+3/4, -z+5/4'
'z, x+1/2, y+1/2'
'z+1/2, -x+3/4, -y+5/4'
'-z+1/4, -x+5/4, y+1'
'-z+3/4, x+1, -y+3/4'
'y, z+1/2, x+1/2'
'-y+3/4, z+1, -x+3/4'
'y+1/2, -z+3/4, -x+5/4'
'-y+1/4, -z+5/4, x+1'
'y+3/4, x+3/4, -z+1/2'
'-y+1/2, -x+1, -z+1'
'y+1/4, -x+1/2, z+5/4'
'-y, x+5/4, z+3/4'
'x+3/4, z+3/4, -y+1/2'
'-x, z+5/4, y+3/4'
'-x+1/2, -z+1, -y+1'
'x+1/4, -z+1/2, y+5/4'
'z+3/4, y+3/4, -x+1/2'
'z+1/4, -y+1/2, x+5/4'
'-z, y+5/4, x+3/4'
'-z+1/2, -y+1, -x+1'
'x+1/2, y, z+1/2'
'-x+3/4, -y+3/4, z+1'
'-x+5/4, y+1/2, -z+3/4'
'x+1, -y+1/4, -z+5/4'
'z+1/2, x, y+1/2'
'z+1, -x+1/4, -y+5/4'
'-z+3/4, -x+3/4, y+1'
'-z+5/4, x+1/2, -y+3/4'
'y+1/2, z, x+1/2'
'-y+5/4, z+1/2, -x+3/4'
'y+1, -z+1/4, -x+5/4'
'-y+3/4, -z+3/4, x+1'
'y+5/4, x+1/4, -z+1/2'
'-y+1, -x+1/2, -z+1'
'y+3/4, -x, z+5/4'
'-y+1/2, x+3/4, z+3/4'
'x+5/4, z+1/4, -y+1/2'
'-x+1/2, z+3/4, y+3/4'
'-x+1, -z+1/2, -y+1'
'x+3/4, -z, y+5/4'
'z+5/4, y+1/4, -x+1/2'
'z+3/4, -y, x+5/4'
'-z+1/2, y+3/4, x+3/4'
'-z+1, -y+1/2, -x+1'
'x+1/2, y+1/2, z'
'-x+3/4, -y+5/4, z+1/2'
'-x+5/4, y+1, -z+1/4'
'x+1, -y+3/4, -z+3/4'
'z+1/2, x+1/2, y'
'z+1, -x+3/4, -y+3/4'
'-z+3/4, -x+5/4, y+1/2'
'-z+5/4, x+1, -y+1/4'
'y+1/2, z+1/2, x'
'-y+5/4, z+1, -x+1/4'
'y+1, -z+3/4, -x+3/4'
'-y+3/4, -z+5/4, x+1/2'
'y+5/4, x+3/4, -z'
'-y+1, -x+1, -z+1/2'
'y+3/4, -x+1/2, z+3/4'
'-y+1/2, x+5/4, z+1/4'
'x+5/4, z+3/4, -y'
'-x+1/2, z+5/4, y+1/4'
'-x+1, -z+1, -y+1/2'
'x+3/4, -z+1/2, y+3/4'
'z+5/4, y+3/4, -x'
'z+3/4, -y+1/2, x+3/4'
'-z+1/2, y+5/4, x+1/4'
'-z+1, -y+1, -x+1/2'
'-x, -y, -z'
'x-1/4, y-3/4, -z-1/2'
'x-3/4, -y-1/2, z-1/4'
'-x-1/2, y-1/4, z-3/4'
'-z, -x, -y'
'-z-1/2, x-1/4, y-3/4'
'z-1/4, x-3/4, -y-1/2'
'z-3/4, -x-1/2, y-1/4'
'-y, -z, -x'
'y-3/4, -z-1/2, x-1/4'
'-y-1/2, z-1/4, x-3/4'
'y-1/4, z-3/4, -x-1/2'
'-y-3/4, -x-1/4, z'
'y-1/2, x-1/2, z-1/2'
'-y-1/4, x, -z-3/4'
'y, -x-3/4, -z-1/4'
'-x-3/4, -z-1/4, y'
'x, -z-3/4, -y-1/4'
'x-1/2, z-1/2, y-1/2'
'-x-1/4, z, -y-3/4'
'-z-3/4, -y-1/4, x'
'-z-1/4, y, -x-3/4'
'z, -y-3/4, -x-1/4'
'z-1/2, y-1/2, x-1/2'
'-x, -y+1/2, -z+1/2'
'x-1/4, y-1/4, -z'
'x-3/4, -y, z+1/4'
'-x-1/2, y+1/4, z-1/4'
'-z, -x+1/2, -y+1/2'
'-z-1/2, x+1/4, y-1/4'
'z-1/4, x-1/4, -y'
'z-3/4, -x, y+1/4'
'-y, -z+1/2, -x+1/2'
'y-3/4, -z, x+1/4'
'-y-1/2, z+1/4, x-1/4'
'y-1/4, z-1/4, -x'
'-y-3/4, -x+1/4, z+1/2'
'y-1/2, x, z'
'-y-1/4, x+1/2, -z-1/4'
'y, -x-1/4, -z+1/4'
'-x-3/4, -z+1/4, y+1/2'
'x, -z-1/4, -y+1/4'
'x-1/2, z, y'
'-x-1/4, z+1/2, -y-1/4'
'-z-3/4, -y+1/4, x+1/2'
'-z-1/4, y+1/2, -x-1/4'
'z, -y-1/4, -x+1/4'
'z-1/2, y, x'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-3/4, -z'
'x-1/4, -y-1/2, z+1/4'
'-x, y-1/4, z-1/4'
'-z+1/2, -x, -y+1/2'
'-z, x-1/4, y-1/4'
'z+1/4, x-3/4, -y'
'z-1/4, -x-1/2, y+1/4'
'-y+1/2, -z, -x+1/2'
'y-1/4, -z-1/2, x+1/4'
'-y, z-1/4, x-1/4'
'y+1/4, z-3/4, -x'
'-y-1/4, -x-1/4, z+1/2'
'y, x-1/2, z'
'-y+1/4, x, -z-1/4'
'y+1/2, -x-3/4, -z+1/4'
'-x-1/4, -z-1/4, y+1/2'
'x+1/2, -z-3/4, -y+1/4'
'x, z-1/2, y'
'-x+1/4, z, -y-1/4'
'-z-1/4, -y-1/4, x+1/2'
'-z+1/4, y, -x-1/4'
'z+1/2, -y-3/4, -x+1/4'
'z, y-1/2, x'
'-x+1/2, -y+1/2, -z'
'x+1/4, y-1/4, -z-1/2'
'x-1/4, -y, z-1/4'
'-x, y+1/4, z-3/4'
'-z+1/2, -x+1/2, -y'
'-z, x+1/4, y-3/4'
'z+1/4, x-1/4, -y-1/2'
'z-1/4, -x, y-1/4'
'-y+1/2, -z+1/2, -x'
'y-1/4, -z, x-1/4'
'-y, z+1/4, x-3/4'
'y+1/4, z-1/4, -x-1/2'
'-y-1/4, -x+1/4, z'
'y, x, z-1/2'
'-y+1/4, x+1/2, -z-3/4'
'y+1/2, -x-1/4, -z-1/4'
'-x-1/4, -z+1/4, y'
'x+1/2, -z-1/4, -y-1/4'
'x, z, y-1/2'
'-x+1/4, z+1/2, -y-3/4'
'-z-1/4, -y+1/4, x'
'-z+1/4, y+1/2, -x-3/4'
'z+1/2, -y-1/4, -x-1/4'
'z, y, x-1/2'

_cell_length_a                   36.4661(5)
_cell_length_b                   36.4661(5)
_cell_length_c                   36.4661(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     48492(2)
_cell_formula_units_Z            96
_cell_measurement_reflns_used    20403
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      66.8220
_cell_measurement_theta_min      4.1800
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             18624
_exptl_crystal_preparation       
'milling with acetonitrille and trimesic acid, recrystallization from acetonitrille, acetic acid solution 1:1'
_exptl_crystal_recrystallization_method evaporation
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            125860
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.766
_diffrn_reflns_theta_min         3.428
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_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     19.00  82.00   0.50   10.00    --    0.00  30.00 -60.00  126
  2  ω    -83.00  81.00   0.50   20.00    --    5.00  30.00  90.00  328
  3  ω   -141.00-115.00   0.50   20.00    --  -90.00  60.00  16.14   52
  4  ω    -52.00  -2.00   0.50   20.00    --  -90.00  60.00  16.14  100
  5  ω   -158.00 -84.00   0.50   20.00    --  -90.00  59.00 -26.53  148
  6  ω    -44.00 -18.00   0.50   20.00    --  -90.00  59.00 -26.53   52
  7  ω   -178.00 -96.00   0.50   20.00    --  -90.00  50.00 150.00  164
  8  ω   -176.00 -57.00   0.50   20.00    --  -90.00  60.00  35.03  238
  9  ω    -76.00  -3.00   0.50   20.00    --  -90.00  50.00 150.00  146
 10  ω   -148.00 -79.00   0.50   20.00    --  -90.00  59.00  83.24  138
 11  ω    -72.00  -8.00   0.50   20.00    --  -90.00  59.00  83.24  128
 12  ω   -179.00-122.00   0.50   20.00    --  -90.00  40.00 -90.00  114
 13  ω   -109.00 -83.00   0.50   20.00    --  -90.00  40.00 -90.00   52
 14  ω   -171.00-119.00   0.50   20.00    --  -90.00  60.00 164.09  104
 15  ω   -105.00 -46.00   0.50   20.00    --  -90.00  60.00 164.09  118
 16  ω    -88.00 -62.00   0.50   20.00    --  -90.00  60.00  16.14   52
 17  ω    -50.00  -2.00   0.50   20.00    --  -90.00  60.00  35.03   96
 18  ω    -58.00 -22.00   0.50   20.00    --  -90.00  60.00-125.08   72
 19  ω   -179.00-114.00   0.50   20.00    --  -90.00  60.00 -59.58  130
 20  ω    -58.00  -3.00   0.50   20.00    --  -90.00  60.00 -59.58  110
 21  ω   -134.00  -2.00   0.50   20.00    --  -90.00  20.00-120.00  264
 22  ω   -175.00-142.00   0.50   20.00    --  -90.00  60.00  97.15   66
 23  ω   -118.00 -93.00   0.50   20.00    --  -90.00  60.00  97.15   50
 24  ω    -60.00  -7.00   0.50   20.00    --  -90.00  60.00  97.15  106
 25  ω    -56.00  -5.00   0.50   20.00    --  -90.00  40.00 120.00  102
 26  ω   -152.00-127.00   0.50   20.00    --  -90.00  10.00 -90.00   50
 27  ω    -51.00 -10.00   0.50   20.00    --  -90.00  10.00 -90.00   82
 28  ω    -93.00 -67.00   0.50   20.00    --  -90.00  40.00 -60.00   52
 29  ω   -174.00-149.00   0.50   20.00    --  -90.00  60.00-171.63   50
 30  ω    -47.00 -22.00   0.50   20.00    --  -90.00  60.00-171.63   50
 31  ω   -176.00 -77.00   0.50   20.00    --  -90.00  60.00-125.08  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0158972000
_diffrn_orient_matrix_UB_12      0.0279869000
_diffrn_orient_matrix_UB_13      -0.0273768000
_diffrn_orient_matrix_UB_21      -0.0376719000
_diffrn_orient_matrix_UB_22      -0.0029541000
_diffrn_orient_matrix_UB_23      0.0189039000
_diffrn_orient_matrix_UB_31      0.0106070000
_diffrn_orient_matrix_UB_32      0.0314925000
_diffrn_orient_matrix_UB_33      0.0260683000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                1441
_reflns_number_total             1872
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.01
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1872
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.072
_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)+(0.1069P)²+19.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1811
_refine_special_details          'The H1 atom position is not precisse'
_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(H3O), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1O), O2(H2O)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.33809(7) 0.77704(6) 0.42110(9) 0.1667(10) Uani 1 1 d . . . . .
H1O H 0.318704 0.788048 0.418149 0.250 Uiso 1 1 calc R U . . .
O2 O 0.28976(5) 0.51432(5) 0.45530(6) 0.1182(6) Uani 1 1 d . . . . .
H2O H 0.268750 0.511178 0.462661 0.177 Uiso 1 1 calc R U . . .
C1 C 0.26834(5) 0.57429(6) 0.43856(5) 0.0808(5) Uani 1 1 d . . . . .
C2 C 0.27640(5) 0.61131(5) 0.43507(5) 0.0780(5) Uani 1 1 d . . . . .
H3O H 0.257777 0.627125 0.427757 0.094 Uiso 1 1 calc R U . . .
C3 C 0.31097(5) 0.62596(6) 0.44198(5) 0.0765(5) Uani 1 1 d . . . . .
C4 C 0.33815(5) 0.60118(6) 0.45290(5) 0.0864(6) Uani 1 1 d . . . . .
H4 H 0.361753 0.609758 0.457342 0.104 Uiso 1 1 calc R U . . .
C5 C 0.33086(5) 0.56483(7) 0.45717(6) 0.0945(6) Uani 1 1 d . . . . .
H5 H 0.349505 0.549056 0.464517 0.113 Uiso 1 1 calc R U . . .
C6 C 0.29606(5) 0.55097(6) 0.45074(6) 0.0893(6) Uani 1 1 d . . . . .
C7 C 0.31823(5) 0.66554(6) 0.43674(5) 0.0792(5) Uani 1 1 d . . . . .
C8 C 0.29057(6) 0.69149(7) 0.44102(6) 0.0941(6) Uani 1 1 d . . . . .
H8 H 0.267287 0.683672 0.447875 0.113 Uiso 1 1 calc R U . . .
C9 C 0.29652(7) 0.72829(7) 0.43546(7) 0.1112(8) Uani 1 1 d . . . . .
H9 H 0.277363 0.744917 0.438057 0.133 Uiso 1 1 calc R U . . .
C10 C 0.33107(8) 0.74040(7) 0.42602(8) 0.1167(8) Uani 1 1 d . . . . .
C11 C 0.35892(7) 0.71518(7) 0.42147(7) 0.1093(7) Uani 1 1 d . . . . .
H11 H 0.382241 0.723157 0.414914 0.131 Uiso 1 1 calc R U . . .
C12 C 0.35251(5) 0.67840(7) 0.42653(6) 0.0935(6) Uani 1 1 d . . . . .
H12 H 0.371549 0.661796 0.423035 0.112 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
O1 H1O 0.8200 . ?
O1 C10 1.372(3) . ?
O2 H2O 0.8200 . ?
O2 C6 1.367(3) . ?
C1 C1 1.493(4) 43 ?
C1 C2 1.387(3) . ?
C1 C6 1.394(3) . ?
C2 H3O 0.9300 . ?
C2 C3 1.392(2) . ?
C3 C4 1.399(3) . ?
C3 C7 1.480(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.361(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C7 C8 1.392(3) . ?
C7 C12 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(4) . ?
C10 C11 1.380(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(3) . ?
C12 H12 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
C10 O1 H1O 109.5 . . ?
C6 O2 H2O 109.5 . . ?
C2 C1 C1 117.81(14) . 43 ?
C2 C1 C6 117.98(17) . . ?
C6 C1 C1 123.96(17) . 43 ?
C1 C2 H3O 118.4 . . ?
C1 C2 C3 123.27(17) . . ?
C3 C2 H3O 118.4 . . ?
C2 C3 C4 116.44(19) . . ?
C2 C3 C7 120.86(17) . . ?
C4 C3 C7 122.67(16) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.55(18) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.97(18) . . ?
C6 C5 H5 119.5 . . ?
O2 C6 C1 120.91(18) . . ?
O2 C6 C5 119.34(18) . . ?
C5 C6 C1 119.7(2) . . ?
C8 C7 C3 121.27(17) . . ?
C12 C7 C3 121.74(18) . . ?
C12 C7 C8 117.0(2) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
O1 C10 C9 121.0(3) . . ?
O1 C10 C11 119.7(3) . . ?
C9 C10 C11 119.3(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 H12 119.3 . . ?

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
O1 C10 C11 C12 179.5(2) . . . . ?
C1 C1 C2 C3 -172.25(19) 43 . . . ?
C1 C1 C6 O2 -7.0(3) 43 . . . ?
C1 C1 C6 C5 170.8(2) 43 . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C7 178.17(17) . . . . ?
C2 C1 C6 O2 179.00(19) . . . . ?
C2 C1 C6 C5 -3.2(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C7 C8 29.1(3) . . . . ?
C2 C3 C7 C12 -149.35(18) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C7 C8 C9 -178.5(2) . . . . ?
C3 C7 C12 C11 179.5(2) . . . . ?
C4 C3 C7 C8 -152.87(19) . . . . ?
C4 C3 C7 C12 28.7(3) . . . . ?
C4 C5 C6 O2 180.0(2) . . . . ?
C4 C5 C6 C1 2.1(3) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
C7 C3 C4 C5 -179.32(19) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
C8 C9 C10 O1 -178.5(3) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C7 -0.8(4) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 7.4 0.0 ?
2 0.125 0.125 0.125 470.7 109.3 '12 H2O'
3 -0.125 -0.125 0.375 470.7 109.1 '12 H2O'
4 0.000 0.000 0.500 7.4 0.0 ?
5 0.125 0.125 0.625 470.7 109.3 '12 H2O'
6 -0.125 -0.125 0.875 470.7 109.2 '12 H2O'
7 0.000 0.250 0.250 7.4 0.0 ?
8 0.000 0.250 0.750 7.4 0.0 ?
9 -0.125 0.375 0.875 470.7 109.1 '12 H2O'
10 -0.125 0.375 0.375 470.7 109.2 '12 H2O'
11 0.000 0.500 0.000 7.4 0.0 ?
12 0.000 0.500 0.500 7.4 0.0 ?
13 0.125 0.625 0.125 470.7 109.3 '12 H2O'
14 0.125 0.625 0.625 470.7 109.3 '12 H2O'
15 0.000 0.750 0.250 7.4 0.0 ?
16 0.000 0.750 0.750 7.4 0.0 ?
17 0.250 0.000 0.250 7.4 0.0 ?
18 0.250 0.000 0.750 7.4 0.0 ?
19 0.250 0.250 0.000 7.4 0.0 ?
20 0.250 0.250 0.500 7.4 0.0 ?
21 0.250 0.500 0.250 7.4 0.0 ?
22 0.250 0.500 0.750 7.4 0.0 ?
23 0.250 0.750 0.000 7.4 0.0 ?
24 0.250 0.750 0.500 7.4 0.0 ?
25 0.375 -0.125 0.375 470.7 109.2 '12 H2O'
26 0.375 0.375 0.875 470.7 109.2 '12 H2O'
27 0.375 0.375 0.375 470.7 109.1 '12 H2O'
28 0.375 0.875 0.875 470.7 109.1 '12 H2O'
29 0.500 0.000 0.000 7.4 0.0 ?
30 0.500 0.000 0.500 7.4 0.0 ?
31 0.500 0.250 0.250 7.4 0.0 ?
32 0.500 0.250 0.750 7.4 0.0 ?
33 0.500 0.500 0.000 7.4 0.0 ?
34 0.500 0.500 0.500 7.4 0.0 ?
35 0.500 0.750 0.250 7.4 0.0 ?
36 0.500 0.750 0.750 7.4 0.0 ?
37 0.625 0.125 0.625 470.7 109.3 '12 H2O'
38 0.625 0.125 0.125 470.7 109.3 '12 H2O'
39 0.625 0.625 0.125 470.7 109.3 '12 H2O'
40 0.625 0.625 0.625 470.7 109.3 '12 H2O'
41 0.750 0.000 0.250 7.4 0.0 ?
42 0.750 0.000 0.750 7.4 0.0 ?
43 0.750 0.250 0.000 7.4 0.0 ?
44 0.750 0.250 0.500 7.4 0.0 ?
45 0.750 0.500 0.250 7.4 0.0 ?
46 0.750 0.500 0.750 7.4 0.0 ?
47 0.750 0.750 0.000 7.4 0.0 ?
48 0.750 0.750 0.500 7.4 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method oil
_olex2_submission_original_sample_id BHDB
_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 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.792
####################################################################### 
# 
# 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_563
_audit_block_doi                 10.5517/ccdc.csd.cc2781g1
_database_code_depnum_ccdc_archive 'CCDC 2063312'
loop_
_audit_author_name
_audit_author_address
'Konrad Dyk'
;University of Maria Curie Sklodowska in Lublin
Poland
;
_audit_update_record             
;
2021-02-16 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
konrad.dyk@poczta.umcs.lublin.pl
_chemical_name_common            DHBD
_chemical_name_systematic        
5,5?-bis(4-hydroxyphenyl)-2,2?-dihydroxy-1,1?-biphenyl
_chemical_formula_moiety         'C24 H18 O4'
_chemical_formula_sum            'C24 H18 O4'
_chemical_formula_weight         370.38
_chemical_melting_point          523
_chemical_oxdiff_formula         C12H4O2
_chemical_oxdiff_usercomment     2294-5
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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.3993(4)
_cell_length_b                   8.82171(15)
_cell_length_c                   9.76280(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.1304(17)
_cell_angle_gamma                90
_cell_volume                     1749.84(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7741
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7000
_cell_measurement_theta_min      4.3070
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.747
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59609
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_preparation       'Evoparoation from acetonitrille'
_exptl_crystal_recrystallization_method 'Crystallization from acetonitrille'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12203
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.256
_diffrn_reflns_theta_min         4.352
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2763
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  31.00   1.00    3.00    --   40.94 -57.00 -30.00   57
  2  ω      3.00  79.00   1.00    3.00    --   40.94-125.00 -60.00   76
  3  ω     58.00 138.00   1.00   12.00    --  112.00 -45.00 -90.00   80
  4  ω    109.00 140.00   1.00   12.00    --  112.00 -61.00   0.00   31
  5  ω     58.00 116.00   1.00   12.00    --  112.00-111.00  60.00   58
  6  ω     37.00 144.00   1.00   12.00    --  112.00 -77.00  60.00  107
  7  ω     84.00 115.00   1.00   12.00    --  112.00  61.00 -30.00   31
  8  ω    121.00 158.00   1.00   12.00    --  112.00  77.00 -60.00   37
  9  ω    117.00 148.00   1.00   12.00    --  112.00 111.00 -60.00   31
 10  ω    116.00 157.00   1.00   12.00    --  112.00  77.00 -90.00   41
 11  ω    122.00 157.00   1.00   12.00    --  112.00  77.00-120.00   35
 12  ω     85.00 157.00   1.00   12.00    --  112.00  61.00-180.00   72
 13  ω     84.00 110.00   1.00   12.00    --  112.00  61.00 -60.00   26
 14  ω     84.00 152.00   1.00   12.00    --  112.00  61.00   0.00   68
 15  ω    133.00 158.00   1.00   12.00    --  112.00  61.00  60.00   25
 16  ω    131.00 157.00   1.00   12.00    --  112.00  61.00  90.00   26
 17  ω    119.00 144.00   1.00   12.00    --  112.00  77.00 150.00   25
 18  ω     84.00 158.00   1.00   12.00    --  112.00  61.00  30.00   74
 19  ω     85.00 118.00   1.00   12.00    --  112.00  61.00 -90.00   33
 20  ω     83.00 109.00   1.00   12.00    --  112.00  61.00-120.00   26
 21  ω     83.00 111.00   1.00   12.00    --  112.00  61.00-150.00   28
 22  ω     87.00 113.00   1.00   12.00    --  112.00  45.00-180.00   26
 23  ω     79.00 106.00   1.00   12.00    --  112.00  77.00-120.00   27
 24  ω     80.00 156.00   1.00   12.00    --  112.00  77.00-150.00   76
 25  ω     79.00 105.00   1.00   12.00    --  112.00  77.00 -60.00   26
 26  ω     80.00 106.00   1.00   12.00    --  112.00  77.00 -90.00   26
 27  ω     79.00 123.00   1.00   12.00    --  112.00  77.00 -30.00   44
 28  ω     79.00 158.00   1.00   12.00    --  112.00  77.00  60.00   79
 29  ω     80.00 105.00   1.00   12.00    --  112.00  77.00 120.00   25
 30  ω     83.00 158.00   1.00   12.00    --  112.00  61.00 120.00   75
 31  ω     79.00 104.00   1.00   12.00    --  112.00  77.00 150.00   25
 32  ω     83.00 109.00   1.00   12.00    --  112.00  61.00 150.00   26
 33  ω     83.00 110.00   1.00   12.00    --  112.00  61.00  90.00   27
 34  ω     84.00 110.00   1.00   12.00    --  112.00  61.00  60.00   26
 35  ω     79.00 105.00   1.00   12.00    --  112.00  77.00   0.00   26
 36  ω     80.00 106.00   1.00   12.00    --  112.00  77.00  30.00   26
 37  ω     79.00 104.00   1.00   12.00    --  112.00  77.00  90.00   25
 38  ω     22.00 111.00   1.00    3.00    --   40.94  37.00  60.00   89
 39  ω     24.00 108.00   1.00    3.00    --   40.94  37.00-120.00   84
 40  ω     80.00 105.00   1.00   12.00    --  112.00  77.00-180.00   25
 41  ω      9.00  58.00   1.00    3.00    --   40.94  77.00-180.00   49
 42  ω      9.00  92.00   1.00    3.00    --   40.94-125.00  90.00   83
 43  ω     29.00 102.00   1.00   12.00    --  112.00 -94.00 -30.00   73
 44  ω     36.00 116.00   1.00   12.00    --  112.00-111.00-120.00   80
 45  ω     29.00  84.00   1.00   12.00    --  112.00 -94.00 -90.00   55
 46  ω    -25.00  64.00   1.00    3.00    --   40.94 -57.00 120.00   89
 47  ω      9.00  57.00   1.00    3.00    --   40.94  77.00   0.00   48
 48  ω      8.00 115.00   1.00    3.00    --   40.94  77.00 -90.00  107
 49  ω      9.00 117.00   1.00    3.00    --   40.94  77.00  90.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0435307000
_diffrn_orient_matrix_UB_12      -0.1214159000
_diffrn_orient_matrix_UB_13      -0.0600214000
_diffrn_orient_matrix_UB_21      -0.0046726000
_diffrn_orient_matrix_UB_22      0.0855494000
_diffrn_orient_matrix_UB_23      -0.1381184000
_diffrn_orient_matrix_UB_31      0.0619177000
_diffrn_orient_matrix_UB_32      0.0918540000
_diffrn_orient_matrix_UB_33      0.0491664000
_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              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1724
_reflns_number_total             1821
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.01
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.078
_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)+(0.0563P)²+0.8901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1093
_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), C11(H11), C2(H2A), C8(H8), C9(H9), C5(H5), C4(H4)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 0.41868(4) 0.86038(12) 0.38101(9) 0.0434(3) Uani 1 1 d . . . . .
H1 H 0.404691 0.903727 0.446757 0.065 Uiso 1 1 calc R U . . .
O2 O 0.86531(4) 0.48689(11) 0.63138(10) 0.0438(3) Uani 1 1 d . . . . .
H2 H 0.883370 0.538622 0.693548 0.066 Uiso 1 1 calc R U . . .
C12 C 0.70802(6) 0.68791(14) 0.64186(11) 0.0333(3) Uani 1 1 d . . . . .
H12 H 0.690448 0.770373 0.685323 0.040 Uiso 1 1 calc R U . . .
C7 C 0.66757(5) 0.60483(14) 0.54621(11) 0.0312(3) Uani 1 1 d . . . . .
C10 C 0.80014(5) 0.52807(14) 0.60919(12) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.59953(5) 0.65785(14) 0.50468(12) 0.0324(3) Uani 1 1 d . . . . .
C11 C 0.77359(6) 0.65077(14) 0.67371(12) 0.0339(3) Uani 1 1 d . . . . .
H11 H 0.799585 0.707634 0.737800 0.041 Uiso 1 1 calc R U . . .
C2 C 0.57319(5) 0.65354(13) 0.36770(12) 0.0315(3) Uani 1 1 d . . . . .
H2A H 0.596887 0.605496 0.303151 0.038 Uiso 1 1 calc R U . . .
C1 C 0.51253(5) 0.71881(14) 0.32424(11) 0.0303(3) Uani 1 1 d . . . . .
C6 C 0.47727(5) 0.78981(15) 0.42267(12) 0.0331(3) Uani 1 1 d . . . . .
C8 C 0.69512(6) 0.48042(15) 0.48522(14) 0.0388(3) Uani 1 1 d . . . . .
H8 H 0.669073 0.421678 0.422742 0.047 Uiso 1 1 calc R U . . .
C9 C 0.76081(6) 0.44247(14) 0.51601(14) 0.0393(3) Uani 1 1 d . . . . .
H9 H 0.778422 0.359192 0.473824 0.047 Uiso 1 1 calc R U . . .
C5 C 0.50189(6) 0.79155(17) 0.55976(12) 0.0408(3) Uani 1 1 d . . . . .
H5 H 0.477735 0.836915 0.625010 0.049 Uiso 1 1 calc R U . . .
C4 C 0.56214(6) 0.72621(17) 0.59992(12) 0.0399(3) Uani 1 1 d . . . . .
H4 H 0.577980 0.727950 0.692238 0.048 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
O1 H1 0.8200 . ?
O1 C6 1.3765(13) . ?
O2 H2 0.8200 . ?
O2 C10 1.3766(13) . ?
C12 H12 0.9300 . ?
C12 C7 1.3972(16) . ?
C12 C11 1.3852(16) . ?
C7 C3 1.4862(14) . ?
C7 C8 1.3910(17) . ?
C10 C11 1.3866(17) . ?
C10 C9 1.3824(17) . ?
C3 C2 1.3965(16) . ?
C3 C4 1.3917(17) . ?
C11 H11 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C1 1.3960(15) . ?
C1 C1 1.493(2) 2_655 ?
C1 C6 1.3988(16) . ?
C6 C5 1.3869(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.3879(16) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.3822(16) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C7 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C7 121.78(11) . . ?
C12 C7 C3 119.91(10) . . ?
C8 C7 C12 117.58(10) . . ?
C8 C7 C3 122.32(10) . . ?
O2 C10 C11 123.05(11) . . ?
O2 C10 C9 117.06(11) . . ?
C9 C10 C11 119.88(11) . . ?
C2 C3 C7 121.52(10) . . ?
C4 C3 C7 120.55(10) . . ?
C4 C3 C2 117.69(10) . . ?
C12 C11 C10 119.42(11) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C3 C2 H2A 118.8 . . ?
C1 C2 C3 122.31(10) . . ?
C1 C2 H2A 118.8 . . ?
C2 C1 C1 120.80(11) . 2_655 ?
C2 C1 C6 118.17(10) . . ?
C6 C1 C1 120.97(11) . 2_655 ?
O1 C6 C1 119.06(10) . . ?
O1 C6 C5 120.67(11) . . ?
C5 C6 C1 120.26(10) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.12(11) . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 120.20(11) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.34(11) . . ?
C4 C5 H5 119.8 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.19(11) . . ?
C5 C4 H4 119.4 . . ?

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
O1 C6 C5 C4 -177.16(13) . . . . ?
O2 C10 C11 C12 177.66(11) . . . . ?
O2 C10 C9 C8 -177.92(12) . . . . ?
C12 C7 C3 C2 137.79(12) . . . . ?
C12 C7 C3 C4 -36.38(18) . . . . ?
C12 C7 C8 C9 -1.5(2) . . . . ?
C7 C12 C11 C10 0.07(19) . . . . ?
C7 C3 C2 C1 -172.35(11) . . . . ?
C7 C3 C4 C5 172.52(13) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C3 C7 C8 C9 173.45(12) . . . . ?
C3 C2 C1 C1 176.89(9) . . . 2_655 ?
C3 C2 C1 C6 -0.40(18) . . . . ?
C11 C12 C7 C3 -173.78(11) . . . . ?
C11 C12 C7 C8 1.25(19) . . . . ?
C11 C10 C9 C8 1.0(2) . . . . ?
C2 C3 C4 C5 -1.9(2) . . . . ?
C2 C1 C6 O1 177.30(11) . . . . ?
C2 C1 C6 C5 -1.36(18) . . . . ?
C1 C1 C6 O1 0.02(16) 2_655 . . . ?
C1 C1 C6 C5 -178.64(11) 2_655 . . . ?
C1 C6 C5 C4 1.5(2) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C8 C7 C3 C2 -37.00(18) . . . . ?
C8 C7 C3 C4 148.83(13) . . . . ?
C9 C10 C11 C12 -1.23(19) . . . . ?
C4 C3 C2 C1 1.99(19) . . . . ?

_olex2_exptl_crystal_mounting_method oil
_olex2_submission_original_sample_id BHDB
_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 1.610
_oxdiff_exptl_absorpt_empirical_full_min 0.550
####################################################################### 
# 
# 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_konrad_120k
_audit_block_doi                 10.5517/ccdc.csd.cc27819w
_database_code_depnum_ccdc_archive 'CCDC 2063307'
loop_
_audit_author_name
_audit_author_address
'Konrad Dyk'
;University of Maria Curie Sklodowska in Lublin
Poland
;
_audit_update_record             
;
2021-02-16 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
konrad.dyk@poczta.umcs.lublin.pl
_chemical_name_common            DHBD
_chemical_name_systematic        
5,5?-bis(4-hydroxyphenyl)-2,2?-dihydroxy-1,1?-biphenyl
_chemical_formula_moiety         'C24 H18 O4'
_chemical_formula_sum            'C24 H18 O4'
_chemical_formula_weight         370.38
_chemical_melting_point          523
_chemical_oxdiff_formula         C12H6O2
_chemical_oxdiff_usercomment     'Kryszta Konrada 120K'
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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.3982(4)
_cell_length_b                   8.72673(20)
_cell_length_c                   9.6682(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.154(2)
_cell_angle_gamma                90
_cell_volume                     1714.08(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3684
_cell_measurement_temperature    120.10(10)
_cell_measurement_theta_max      75.5090
_cell_measurement_theta_min      4.3610
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.743
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76097
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_preparation       'Evaporation from acetonitrille'
_exptl_crystal_recrystallization_method 'crystallization from acetonitrille'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5339
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.230
_diffrn_reflns_theta_min         4.353
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.10(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2763
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_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     25.00  59.00   1.00    2.25    --   40.94  37.00  60.00   34
  2  ω     83.00 114.00   1.00    2.25    --   40.94  37.00  60.00   31
  3  ω     44.00  95.00   1.00    9.00    --  112.00 -61.00  90.00   51
  4  ω    114.00 139.00   1.00    9.00    --  112.00 -61.00  90.00   25
  5  ω     71.00 110.00   1.00    9.00    --  112.00-111.00  30.00   39
  6  ω     58.00  97.00   1.00    9.00    --  112.00 -94.00  90.00   39
  7  ω     44.00 137.00   1.00    9.00    --  112.00 -45.00 -30.00   93
  8  ω     83.00 136.00   1.00    9.00    --  112.00  61.00-120.00   53
  9  ω     96.00 148.00   1.00    9.00    --  112.00 111.00  60.00   52
 10  ω     47.00  84.00   1.00    9.00    --  112.00 -61.00 -60.00   37
 11  ω     37.00  63.00   1.00    9.00    --  112.00-111.00  30.00   26
 12  ω     29.00  54.00   1.00    9.00    --  112.00 -94.00 -30.00   25
 13  ω     40.00 109.00   1.00    9.00    --  112.00 -94.00 -90.00   69
 14  ω     84.00 116.00   1.00    9.00    --  112.00-111.00-180.00   32
 15  ω     38.00  64.00   1.00    9.00    --  112.00-111.00-180.00   26
 16  ω     26.00 155.00   1.00    9.00    --  112.00   0.00-120.00  129
 17  ω     41.00  90.00   1.00    9.00    --  112.00 -61.00 150.00   49
 18  ω     11.00  98.00   1.00    2.25    --   40.94  77.00  90.00   87
 19  ω     13.00 110.00   1.00    2.25    --   40.94  57.00-150.00   97
 20  ω    -69.00  32.00   1.00    2.25    --  -40.94  57.00 -30.00  101
 21  ω    -95.00 -65.00   1.00    2.25    --  -40.94 125.00 -90.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0454535000
_diffrn_orient_matrix_UB_12      -0.1237479000
_diffrn_orient_matrix_UB_13      -0.0527232000
_diffrn_orient_matrix_UB_21      -0.0033987000
_diffrn_orient_matrix_UB_22      0.0798132000
_diffrn_orient_matrix_UB_23      -0.1426867000
_diffrn_orient_matrix_UB_31      0.0605873000
_diffrn_orient_matrix_UB_32      0.0974318000
_diffrn_orient_matrix_UB_33      0.0495640000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1655
_reflns_number_total             1766
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.01
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.063
_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)+(0.0481P)²+1.4506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0975
_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), C11(H11), C4(H4), C2(H2A), C9(H9), C8(H8), C5(H5)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13287(4) 0.51149(10) 0.36789(9) 0.0209(2) Uani 1 1 d . . . . .
H1 H 0.114449 0.456587 0.307481 0.031 Uiso 1 1 calc R U . . .
O2 O 0.58099(4) 0.13895(10) 0.61748(9) 0.0201(2) Uani 1 1 d . . . . .
C7 C 0.33126(5) 0.39563(13) 0.45231(11) 0.0159(2) Uani 1 1 d . . . . .
C10 C 0.19825(5) 0.47059(13) 0.38983(11) 0.0159(2) Uani 1 1 d . . . . .
C12 C 0.29076(5) 0.31005(13) 0.35619(11) 0.0163(2) Uani 1 1 d . . . . .
H12 H 0.308494 0.226764 0.312514 0.020 Uiso 1 1 calc R U . . .
C3 C 0.39952(5) 0.34284(13) 0.49353(12) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.22498(5) 0.34637(13) 0.32459(11) 0.0168(3) Uani 1 1 d . . . . .
H11 H 0.198982 0.288221 0.260388 0.020 Uiso 1 1 calc R U . . .
C1 C 0.48735(5) 0.28303(13) 0.67522(11) 0.0153(2) Uani 1 1 d . . . . .
C6 C 0.52215(5) 0.21008(13) 0.57576(12) 0.0162(2) Uani 1 1 d . . . . .
C4 C 0.43643(6) 0.27248(14) 0.39700(12) 0.0191(3) Uani 1 1 d . . . . .
H4 H 0.420151 0.269594 0.304046 0.023 Uiso 1 1 calc R U . . .
C2 C 0.42633(5) 0.34897(13) 0.63179(12) 0.0158(2) Uani 1 1 d . . . . .
H2A H 0.402898 0.398384 0.696923 0.019 Uiso 1 1 calc R U . . .
C9 C 0.23759(6) 0.55873(13) 0.48358(12) 0.0195(3) Uani 1 1 d . . . . .
H9 H 0.219824 0.642824 0.526013 0.023 Uiso 1 1 calc R U . . .
C8 C 0.30368(6) 0.52125(14) 0.51413(12) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.329768 0.581093 0.576781 0.023 Uiso 1 1 calc R U . . .
C5 C 0.49703(5) 0.20669(14) 0.43719(12) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.520957 0.160143 0.371303 0.023 Uiso 1 1 calc R U . . .
H2 H 0.5934(9) 0.093(2) 0.546(2) 0.039(5) Uiso 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
O1 H1 0.8200 . ?
O1 C10 1.3785(13) . ?
O2 C6 1.3789(13) . ?
O2 H2 0.85(2) . ?
C7 C12 1.4021(15) . ?
C7 C3 1.4867(14) . ?
C7 C8 1.3913(16) . ?
C10 C11 1.3900(16) . ?
C10 C9 1.3881(16) . ?
C12 H12 0.9300 . ?
C12 C11 1.3858(15) . ?
C3 C4 1.3933(16) . ?
C3 C2 1.3991(15) . ?
C11 H11 0.9300 . ?
C1 C1 1.491(2) 2_656 ?
C1 C6 1.3988(16) . ?
C1 C2 1.4011(15) . ?
C6 C5 1.3911(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.3864(15) . ?
C2 H2A 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.3928(15) . ?
C8 H8 0.9300 . ?
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
C10 O1 H1 109.5 . . ?
C6 O2 H2 106.7(12) . . ?
C12 C7 C3 119.64(10) . . ?
C8 C7 C12 117.88(10) . . ?
C8 C7 C3 122.28(10) . . ?
O1 C10 C11 123.07(10) . . ?
O1 C10 C9 116.85(10) . . ?
C9 C10 C11 120.07(10) . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.70(11) . . ?
C11 C12 H12 119.2 . . ?
C4 C3 C7 120.43(10) . . ?
C4 C3 C2 117.94(10) . . ?
C2 C3 C7 121.37(10) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.33(10) . . ?
C12 C11 H11 120.3 . . ?
C6 C1 C1 120.92(11) . 2_656 ?
C6 C1 C2 118.23(10) . . ?
C2 C1 C1 120.76(11) . 2_656 ?
O2 C6 C1 119.08(10) . . ?
O2 C6 C5 120.51(10) . . ?
C5 C6 C1 120.40(10) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.10(10) . . ?
C5 C4 H4 119.4 . . ?
C3 C2 C1 122.08(10) . . ?
C3 C2 H2A 119.0 . . ?
C1 C2 H2A 119.0 . . ?
C10 C9 H9 120.0 . . ?
C10 C9 C8 120.01(11) . . ?
C8 C9 H9 120.0 . . ?
C7 C8 C9 120.99(11) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.21(10) . . ?
C4 C5 H5 119.9 . . ?

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
O1 C10 C11 C12 -177.80(10) . . . . ?
O1 C10 C9 C8 178.03(10) . . . . ?
O2 C6 C5 C4 177.09(11) . . . . ?
C7 C12 C11 C10 -0.12(17) . . . . ?
C7 C3 C4 C5 -172.39(11) . . . . ?
C7 C3 C2 C1 172.13(10) . . . . ?
C10 C9 C8 C7 -0.25(18) . . . . ?
C12 C7 C3 C4 35.85(16) . . . . ?
C12 C7 C3 C2 -138.13(12) . . . . ?
C12 C7 C8 C9 1.32(18) . . . . ?
C3 C7 C12 C11 173.74(10) . . . . ?
C3 C7 C8 C9 -173.42(11) . . . . ?
C3 C4 C5 C6 -0.06(19) . . . . ?
C11 C10 C9 C8 -1.06(18) . . . . ?
C1 C1 C6 O2 -0.71(15) 2_656 . . . ?
C1 C1 C6 C5 177.96(9) 2_656 . . . ?
C1 C1 C2 C3 -176.17(9) 2_656 . . . ?
C1 C6 C5 C4 -1.56(18) . . . . ?
C6 C1 C2 C3 0.44(17) . . . . ?
C4 C3 C2 C1 -1.99(17) . . . . ?
C2 C3 C4 C5 1.79(18) . . . . ?
C2 C1 C6 O2 -177.31(10) . . . . ?
C2 C1 C6 C5 1.36(17) . . . . ?
C9 C10 C11 C12 1.23(17) . . . . ?
C8 C7 C12 C11 -1.15(17) . . . . ?
C8 C7 C3 C4 -149.51(12) . . . . ?
C8 C7 C3 C2 36.51(17) . . . . ?

_olex2_exptl_crystal_mounting_method oil
_olex2_submission_original_sample_id BHDB
_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 1.588
_oxdiff_exptl_absorpt_empirical_full_min 0.486
####################################################################### 
# 
# 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_22942
_audit_block_doi                 10.5517/ccdc.csd.cc27614n
_database_code_depnum_ccdc_archive 'CCDC 2061380'
loop_
_audit_author_name
_audit_author_address
'Konrad Dyk'
;University of Maria Curie Sklodowska in Lublin
Poland
;
_audit_update_record             
;
2021-02-17 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
konrad.dyk@poczta.umcs.lublin.pl
_chemical_name_common            BHDB
_chemical_name_systematic        
5,5?-bis(4-hydroxyphenyl)-2,2?-dihydroxy-1,1?-biphenyl
_chemical_formula_moiety         'C24 H18 O4, C3 H6 O, 1.25(H2 O)'
_chemical_formula_sum            'C27 H26.50 O6.25'
_chemical_formula_weight         450.98
_chemical_absolute_configuration .
_chemical_melting_point          523
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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   10.4718(6)
_cell_length_b                   10.6341(5)
_cell_length_c                   11.1086(6)
_cell_angle_alpha                80.520(4)
_cell_angle_beta                 82.650(5)
_cell_angle_gamma                83.754(5)
_cell_volume                     1205.24(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3307
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      74.6370
_cell_measurement_theta_min      4.0370
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.761
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36139
_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            'dull yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             477
_exptl_crystal_preparation       'solvent mixture aceton+water'
_exptl_crystal_recrystallization_method 'low temperature solvent evaporation'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8362
_diffrn_reflns_point_group_measured_fraction_full 0.592
_diffrn_reflns_point_group_measured_fraction_max 0.568
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.116
_diffrn_reflns_theta_min         4.060
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2763
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  63.00   1.00    7.15    --   40.94 -37.00 -30.00   87
  2  ω     42.00 140.00   1.00   28.61    --  112.00 -61.00  90.00   98
  3  ω     85.00 114.00   1.00   28.61    --  112.00-111.00  60.00   29
  4  ω     90.00 141.00   1.00   28.61    --  112.00 -61.00 -30.00   51
  5  ω     83.00 108.00   1.00   28.61    --  112.00 -94.00 -60.00   25
  6  ω     57.00 140.00   1.00   28.61    --  112.00 -77.00-150.00   83
  7  ω     79.00 115.00   1.00   28.61    --  112.00-111.00-180.00   36
  8  ω     40.00  68.00   1.00   28.61    --  112.00 -61.00 -30.00   28
  9  ω     58.00 109.00   1.00   28.61    --  112.00 -94.00  30.00   51
 10  ω     36.00  65.00   1.00   28.61    --  112.00-111.00  60.00   29
 11  ω     32.00  91.00   1.00    7.15    --   40.94-132.00 166.00   59
 12  ω    -23.00 110.00   1.00    7.15    --   40.94   0.00   0.00  133
 13  ω     93.00 158.00   1.00   28.61    --  112.00  61.00 -30.00   65
 14  ω    115.00 156.00   1.00   28.61    --  112.00  45.00 -60.00   41
 15  ω    125.00 158.00   1.00   28.61    --  112.00  45.00-180.00   33
 16  ω     90.00 125.00   1.00   28.61    --  112.00  30.00-180.00   35
 17  ω     82.00 142.00   1.00   28.61    --  112.00 111.00-180.00   60
 18  ω     85.00 154.00   1.00   28.61    --  112.00 111.00  30.00   69
 19  ω     65.00 142.00   1.00   28.61    --  112.00 137.00  53.00   77
 20  ω    -53.00  -3.00   1.00    7.15    --  -40.94 125.00 150.00   50
 21  ω    -92.00 -28.00   1.00    7.15    --  -40.94 125.00-120.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0628294000
_diffrn_orient_matrix_UB_12      -0.0463242000
_diffrn_orient_matrix_UB_13      0.1306736000
_diffrn_orient_matrix_UB_21      0.1128073000
_diffrn_orient_matrix_UB_22      0.0441498000
_diffrn_orient_matrix_UB_23      0.0541539000
_diffrn_orient_matrix_UB_31      -0.0742176000
_diffrn_orient_matrix_UB_32      0.1328624000
_diffrn_orient_matrix_UB_33      0.0035463000
_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              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.181
_reflns_Friedel_fraction_full    0.187
_reflns_Friedel_fraction_max     0.174
_reflns_number_gt                4325
_reflns_number_total             5726
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.01
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         5726
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0802
_refine_ls_restrained_S_all      1.074
_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)+(0.1140P)²+0.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2485
_refine_special_details          
'The O5, O6, O7 water molecules are located in chanels and are partli disordered. This produces B alerts D-H without acceptors O7 --H7A'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 H1O7-H3O'_$2 = H3O'_$2-H2O7
 2.4 with sigma of 0.02
 H1O'-H2O5
 2.3 with sigma of 0.04
3. Others
 Fixed Sof: O6(0.5) H1O6(0.5) H2O6(0.5)
4.a Free rotating group:
 O5(H1O5,H2O5), O6(H1O6,H2O6), O7(H2O7,H1O7)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4A), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C2'(H2'A),
 C4'(H4'A), C5'(H5'), C8'(H8'), C9'(H9'), C11'(H11'), C12'(H12'), C14'(H14'),
 C16'(H16'), C17'(H17'), C20'(H20'), C21'(H21'), C23'(H23'), C24'(H24')
4.c Idealised Me refined as rotating group:
 C1AC(H1AA,H1AB,H1AC), C3AC(H3AA,H3AB,H3AC), C4AC(H4AA,H4AB,H4AC), C6AC(H6AA,
 H6AB,H6AC)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1O), O2(H2O), O3(H3O), O4(H4O), O1'(H1O'), O2'(H2O'), O3'(H3O'), O4'(H4O')
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.7026(6) 0.3765(7) 0.5230(5) 0.0773(16) Uani 1 1 d . . . . .
H1O H 0.781635 0.370986 0.520356 0.116 Uiso 1 1 calc R U . . .
O2 O 0.3057(6) 0.6928(6) 1.2791(5) 0.0680(13) Uani 1 1 d . . . . .
H2O H 0.226713 0.705588 1.282730 0.102 Uiso 1 1 calc R U . . .
O3 O -0.0788(7) 1.2072(8) 0.4900(6) 0.093(2) Uani 1 1 d . . . . .
H3O H -0.013426 1.210729 0.440779 0.140 Uiso 1 1 calc R U . . .
O4 O 0.0712(5) 0.6384(5) 1.2624(4) 0.0636(12) Uani 1 1 d . . . . .
H4O H 0.027118 0.663741 1.321684 0.095 Uiso 1 1 calc R U . . .
C1 C 0.2842(6) 0.6625(5) 1.0709(5) 0.0456(11) Uani 1 1 d . . . . .
C2 C 0.3436(6) 0.6111(5) 0.9687(5) 0.0457(11) Uani 1 1 d . . . . .
H2A H 0.298026 0.619867 0.900789 0.055 Uiso 1 1 calc R U . . .
C3 C 0.4678(6) 0.5469(6) 0.9611(6) 0.0486(12) Uani 1 1 d . . . . .
C4 C 0.5318(7) 0.5305(7) 1.0655(6) 0.0577(14) Uani 1 1 d . . . . .
H4A H 0.613938 0.487270 1.065445 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4731(8) 0.5787(8) 1.1699(7) 0.0651(17) Uani 1 1 d . . . . .
H5 H 0.516668 0.566280 1.239418 0.078 Uiso 1 1 calc R U . . .
C6 C 0.3529(7) 0.6438(6) 1.1734(6) 0.0542(14) Uani 1 1 d . . . . .
C7 C 0.5288(6) 0.5016(6) 0.8463(6) 0.0506(12) Uani 1 1 d . . . . .
C8 C 0.4577(7) 0.4834(7) 0.7539(7) 0.0603(16) Uani 1 1 d . . . . .
H8 H 0.368105 0.498019 0.764797 0.072 Uiso 1 1 calc R U . . .
C9 C 0.5173(7) 0.4439(8) 0.6461(7) 0.0633(17) Uani 1 1 d . . . . .
H9 H 0.467952 0.433666 0.585081 0.076 Uiso 1 1 calc R U . . .
C10 C 0.6480(7) 0.4202(7) 0.6296(6) 0.0593(15) Uani 1 1 d . . . . .
C11 C 0.7226(7) 0.4365(9) 0.7181(7) 0.071(2) Uani 1 1 d . . . . .
H11 H 0.811955 0.418995 0.706880 0.085 Uiso 1 1 calc R U . . .
C12 C 0.6625(7) 0.4796(8) 0.8242(7) 0.0631(16) Uani 1 1 d . . . . .
H12 H 0.713194 0.494295 0.882547 0.076 Uiso 1 1 calc R U . . .
C13 C 0.1548(6) 0.7368(6) 1.0645(6) 0.0486(12) Uani 1 1 d . . . . .
C14 C 0.1320(6) 0.8189(6) 0.9565(6) 0.0496(12) Uani 1 1 d . . . . .
H14 H 0.199832 0.828313 0.893778 0.059 Uiso 1 1 calc R U . . .
C15 C 0.0120(7) 0.8885(6) 0.9369(6) 0.0538(13) Uani 1 1 d . . . . .
C16 C -0.0870(7) 0.8715(7) 1.0336(7) 0.0626(16) Uani 1 1 d . . . . .
H16 H -0.168361 0.914408 1.025071 0.075 Uiso 1 1 calc R U . . .
C17 C -0.0653(8) 0.7918(8) 1.1414(7) 0.0652(17) Uani 1 1 d . . . . .
H17 H -0.131989 0.784865 1.205316 0.078 Uiso 1 1 calc R U . . .
C18 C 0.0498(7) 0.7230(6) 1.1578(6) 0.0553(14) Uani 1 1 d . . . . .
C19 C -0.0101(7) 0.9713(6) 0.8190(6) 0.0541(14) Uani 1 1 d . . . . .
C20 C 0.0927(7) 1.0126(7) 0.7323(7) 0.0594(15) Uani 1 1 d . . . . .
H20 H 0.177296 0.988344 0.749515 0.071 Uiso 1 1 calc R U . . .
C21 C 0.0709(7) 1.0881(7) 0.6230(7) 0.0647(17) Uani 1 1 d . . . . .
H21 H 0.140627 1.111758 0.566247 0.078 Uiso 1 1 calc R U . . .
C22 C -0.0513(8) 1.1286(7) 0.5966(7) 0.0658(18) Uani 1 1 d . . . . .
C23 C -0.1557(8) 1.0894(9) 0.6786(8) 0.072(2) Uani 1 1 d . . . . .
H23 H -0.239660 1.115346 0.660392 0.087 Uiso 1 1 calc R U . . .
C24 C -0.1335(7) 1.0103(8) 0.7890(8) 0.0657(17) Uani 1 1 d . . . . .
H24 H -0.203787 0.983312 0.843476 0.079 Uiso 1 1 calc R U . . .
O1' O 0.3964(8) -0.0071(8) -0.4507(7) 0.093(2) Uani 1 1 d . . . . .
H1O' H 0.457034 -0.038979 -0.493398 0.140 Uiso 1 1 calc DR U . . .
O2' O 0.7168(8) 0.0156(6) 0.3373(6) 0.0890(19) Uani 1 1 d . . . . .
H2O' H 0.679586 0.068400 0.378867 0.134 Uiso 1 1 calc R U . . .
O3' O 1.1933(7) 0.5665(6) -0.4285(6) 0.0786(15) Uani 1 1 d . . . . .
H3O' H 1.226468 0.507341 -0.464039 0.118 Uiso 1 1 calc R U . . .
O4' O 0.6578(7) 0.2698(6) 0.3318(5) 0.0756(15) Uani 1 1 d . . . . .
H4O' H 0.666438 0.310541 0.386377 0.113 Uiso 1 1 calc R U . . .
C1' C 0.6763(7) 0.1266(6) 0.1339(6) 0.0548(14) Uani 1 1 d . . . . .
C2' C 0.6212(7) 0.1193(6) 0.0276(6) 0.0546(13) Uani 1 1 d . . . . .
H2'A H 0.629546 0.186677 -0.037007 0.065 Uiso 1 1 calc R U . . .
C3' C 0.5554(6) 0.0188(6) 0.0121(7) 0.0585(15) Uani 1 1 d . . . . .
C4' C 0.5399(9) -0.0793(8) 0.1133(9) 0.077(2) Uani 1 1 d . . . . .
H4'A H 0.495191 -0.148609 0.107389 0.093 Uiso 1 1 calc R U . . .
C5' C 0.5897(9) -0.0741(7) 0.2195(8) 0.076(2) Uani 1 1 d . . . . .
H5' H 0.575835 -0.139145 0.285600 0.092 Uiso 1 1 calc R U . . .
C6' C 0.6597(8) 0.0241(7) 0.2325(7) 0.0659(18) Uani 1 1 d . . . . .
C7' C 0.5074(7) 0.0126(7) -0.1069(8) 0.0632(16) Uani 1 1 d . . . . .
C8' C 0.4740(8) 0.1199(7) -0.1874(8) 0.0696(19) Uani 1 1 d . . . . .
H8' H 0.476550 0.199851 -0.164706 0.084 Uiso 1 1 calc R U . . .
C9' C 0.4364(9) 0.1135(8) -0.3015(9) 0.076(2) Uani 1 1 d . . . . .
H9' H 0.414715 0.187994 -0.354379 0.092 Uiso 1 1 calc R U . . .
C10' C 0.4317(8) -0.0069(9) -0.3359(9) 0.076(2) Uani 1 1 d . . . . .
C11' C 0.4658(8) -0.1151(8) -0.2569(9) 0.073(2) Uani 1 1 d . . . . .
H11' H 0.464750 -0.195119 -0.279941 0.088 Uiso 1 1 calc R U . . .
C12' C 0.5013(8) -0.1064(7) -0.1450(9) 0.071(2) Uani 1 1 d . . . . .
H12' H 0.522164 -0.181140 -0.092226 0.085 Uiso 1 1 calc R U . . .
C13' C 0.7571(7) 0.2324(6) 0.1349(5) 0.0526(13) Uani 1 1 d . . . . .
C14' C 0.8410(7) 0.2726(5) 0.0308(5) 0.0503(13) Uani 1 1 d . . . . .
H14' H 0.849344 0.227294 -0.035042 0.060 Uiso 1 1 calc R U . . .
C15' C 0.9123(7) 0.3770(6) 0.0213(6) 0.0521(13) Uani 1 1 d . . . . .
C16' C 0.9031(9) 0.4402(8) 0.1238(7) 0.0684(19) Uani 1 1 d . . . . .
H16' H 0.953566 0.507392 0.121923 0.082 Uiso 1 1 calc R U . . .
C17' C 0.8194(9) 0.4032(7) 0.2283(7) 0.0685(19) Uani 1 1 d . . . . .
H17' H 0.814303 0.445567 0.295829 0.082 Uiso 1 1 calc R U . . .
C18' C 0.7441(8) 0.3040(7) 0.2319(6) 0.0614(16) Uani 1 1 d . . . . .
C19' C 0.9935(7) 0.4211(6) -0.0948(6) 0.0546(14) Uani 1 1 d . . . . .
C20' C 1.0510(8) 0.3422(7) -0.1744(7) 0.0652(17) Uani 1 1 d . . . . .
H20' H 1.045186 0.254577 -0.152172 0.078 Uiso 1 1 calc R U . . .
C21' C 1.1168(8) 0.3847(7) -0.2854(7) 0.0653(17) Uani 1 1 d . . . . .
H21' H 1.154476 0.327465 -0.337391 0.078 Uiso 1 1 calc R U . . .
C22' C 1.1265(8) 0.5184(8) -0.3195(7) 0.0641(17) Uani 1 1 d . . . . .
C23' C 1.0705(8) 0.5999(7) -0.2422(7) 0.0645(17) Uani 1 1 d . . . . .
H23' H 1.075891 0.687546 -0.264585 0.077 Uiso 1 1 calc R U . . .
C24' C 1.0056(8) 0.5533(7) -0.1304(7) 0.0616(16) Uani 1 1 d . . . . .
H24' H 0.969152 0.610053 -0.077556 0.074 Uiso 1 1 calc R U . . .
O1AC O 0.1250(11) 1.2399(10) 0.3066(9) 0.126(3) Uani 1 1 d . . . . .
C1AC C 0.141(3) 1.071(2) 0.196(3) 0.205(11) Uani 1 1 d . . . . .
H1AA H 0.179123 1.004269 0.253087 0.308 Uiso 1 1 calc R U . . .
H1AB H 0.172922 1.058154 0.113634 0.308 Uiso 1 1 calc R U . . .
H1AC H 0.048488 1.068853 0.207514 0.308 Uiso 1 1 calc R U . . .
C2AC C 0.1733(12) 1.1940(13) 0.2168(13) 0.101(3) Uani 1 1 d . . . . .
C3AC C 0.261(2) 1.264(2) 0.1229(14) 0.152(7) Uani 1 1 d . . . . .
H3AA H 0.256381 1.238818 0.044808 0.227 Uiso 1 1 calc R U . . .
H3AB H 0.348031 1.245942 0.144099 0.227 Uiso 1 1 calc R U . . .
H3AC H 0.236771 1.354579 0.118317 0.227 Uiso 1 1 calc R U . . .
O2AC O -0.1300(7) 0.6513(7) 1.4333(6) 0.0904(19) Uani 1 1 d . . . . .
C4AC C -0.2643(16) 0.7637(13) 1.5735(13) 0.127(6) Uani 1 1 d . . . . .
H4AA H -0.331614 0.719925 1.552151 0.190 Uiso 1 1 calc R U . . .
H4AB H -0.289108 0.854128 1.562963 0.190 Uiso 1 1 calc R U . . .
H4AC H -0.250454 0.733920 1.657645 0.190 Uiso 1 1 calc R U . . .
C5AC C -0.1444(11) 0.7381(9) 1.4937(7) 0.082(3) Uani 1 1 d . . . . .
C6AC C -0.0422(12) 0.8265(12) 1.4823(12) 0.099(3) Uani 1 1 d . . . . .
H6AA H -0.062505 0.901453 1.424629 0.148 Uiso 1 1 calc R U . . .
H6AB H 0.039370 0.784504 1.453946 0.148 Uiso 1 1 calc R U . . .
H6AC H -0.037011 0.850718 1.560921 0.148 Uiso 1 1 calc R U . . .
O5 O 0.3741(12) -0.2407(9) -0.5046(8) 0.127(4) Uani 1 1 d G . . . .
H1O5 H 0.378654 -0.269226 -0.572243 0.190 Uiso 1 1 d G U . . .
H2O5 H 0.312313 -0.181809 -0.508038 0.190 Uiso 1 1 d DG U . . .
O6 O 0.4076(17) 1.2037(17) 0.3771(19) 0.107(5) Uani 0.5 1 d G . P . .
H1O6 H 0.327991 1.200631 0.371388 0.160 Uiso 0.5 1 d G U P . .
H2O6 H 0.433548 1.128030 0.408046 0.160 Uiso 0.5 1 d G U P . .
O7 O 0.2581(17) 1.3996(11) 0.4206(9) 0.177(7) Uani 1 1 d G . . . .
H2O7 H 0.314557 1.335776 0.425550 0.266 Uiso 1 1 d DG U . . .
H1O7 H 0.259162 1.426050 0.343935 0.266 Uiso 1 1 d DG 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
O1 H1O 0.8200 . ?
O1 C10 1.377(8) . ?
O2 H2O 0.8200 . ?
O2 C6 1.376(7) . ?
O3 H3O 0.8200 . ?
O3 C22 1.376(10) . ?
O4 H4O 0.8200 . ?
O4 C18 1.374(9) . ?
C1 C2 1.387(8) . ?
C1 C6 1.399(9) . ?
C1 C13 1.497(9) . ?
C2 H2A 0.9300 . ?
C2 C3 1.400(8) . ?
C3 C4 1.390(9) . ?
C3 C7 1.481(8) . ?
C4 H4A 0.9300 . ?
C4 C5 1.390(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(11) . ?
C7 C8 1.393(9) . ?
C7 C12 1.391(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.359(10) . ?
C10 C11 1.374(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(9) . ?
C13 C18 1.413(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.411(9) . ?
C15 C16 1.397(10) . ?
C15 C19 1.482(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.357(11) . ?
C19 C20 1.406(9) . ?
C19 C24 1.379(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.371(11) . ?
C21 H21 0.9300 . ?
C21 C22 1.357(12) . ?
C22 C23 1.385(11) . ?
C23 H23 0.9300 . ?
C23 C24 1.398(12) . ?
C24 H24 0.9300 . ?
O1' H1O' 0.8200 . ?
O1' C10' 1.372(11) . ?
O2' H2O' 0.8200 . ?
O2' C6' 1.361(11) . ?
O3' H3O' 0.8200 . ?
O3' C22' 1.369(9) . ?
O4' H4O' 0.8200 . ?
O4' C18' 1.365(10) . ?
C1' C2' 1.395(10) . ?
C1' C6' 1.421(9) . ?
C1' C13' 1.482(9) . ?
C2' H2'A 0.9300 . ?
C2' C3' 1.378(9) . ?
C3' C4' 1.407(11) . ?
C3' C7' 1.488(12) . ?
C4' H4'A 0.9300 . ?
C4' C5' 1.362(14) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.375(12) . ?
C7' C8' 1.371(12) . ?
C7' C12' 1.409(10) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.388(13) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.404(12) . ?
C10' C11' 1.370(14) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.362(13) . ?
C12' H12' 0.9300 . ?
C13' C14' 1.396(9) . ?
C13' C18' 1.403(9) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.387(8) . ?
C15' C16' 1.403(10) . ?
C15' C19' 1.488(10) . ?
C16' H16' 0.9300 . ?
C16' C17' 1.391(12) . ?
C17' H17' 0.9300 . ?
C17' C18' 1.376(11) . ?
C19' C20' 1.359(11) . ?
C19' C24' 1.411(9) . ?
C20' H20' 0.9300 . ?
C20' C21' 1.366(11) . ?
C21' H21' 0.9300 . ?
C21' C22' 1.422(11) . ?
C22' C23' 1.355(12) . ?
C23' H23' 0.9300 . ?
C23' C24' 1.380(11) . ?
C24' H24' 0.9300 . ?
O1AC C2AC 1.211(16) . ?
C1AC H1AA 0.9600 . ?
C1AC H1AB 0.9600 . ?
C1AC H1AC 0.9600 . ?
C1AC C2AC 1.45(3) . ?
C2AC C3AC 1.46(2) . ?
C3AC H3AA 0.9600 . ?
C3AC H3AB 0.9600 . ?
C3AC H3AC 0.9600 . ?
O2AC C5AC 1.214(12) . ?
C4AC H4AA 0.9600 . ?
C4AC H4AB 0.9600 . ?
C4AC H4AC 0.9600 . ?
C4AC C5AC 1.469(15) . ?
C5AC C6AC 1.480(16) . ?
C6AC H6AA 0.9600 . ?
C6AC H6AB 0.9600 . ?
C6AC H6AC 0.9600 . ?
O5 H1O5 0.8500 . ?
O5 H2O5 0.8499 . ?
O6 H1O6 0.8487 . ?
O6 H2O6 0.8514 . ?
O7 H2O7 0.8502 . ?
O7 H1O7 0.8503 . ?

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
C10 O1 H1O 109.5 . . ?
C6 O2 H2O 109.5 . . ?
C22 O3 H3O 109.5 . . ?
C18 O4 H4O 109.5 . . ?
C2 C1 C6 116.7(5) . . ?
C2 C1 C13 119.1(5) . . ?
C6 C1 C13 124.2(5) . . ?
C1 C2 H2A 117.9 . . ?
C1 C2 C3 124.3(5) . . ?
C3 C2 H2A 117.9 . . ?
C2 C3 C7 121.5(5) . . ?
C4 C3 C2 116.8(6) . . ?
C4 C3 C7 121.7(6) . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 C5 120.0(6) . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.8(6) . . ?
C6 C5 H5 119.1 . . ?
O2 C6 C1 122.1(6) . . ?
C5 C6 O2 117.4(6) . . ?
C5 C6 C1 120.4(6) . . ?
C8 C7 C3 122.6(6) . . ?
C12 C7 C3 120.7(6) . . ?
C12 C7 C8 116.7(6) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.5(6) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.9(7) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 O1 117.9(7) . . ?
C9 C10 C11 120.9(6) . . ?
C11 C10 O1 121.2(7) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.9(7) . . ?
C12 C11 H11 120.6 . . ?
C7 C12 H12 118.9 . . ?
C11 C12 C7 122.1(7) . . ?
C11 C12 H12 118.9 . . ?
C14 C13 C1 118.4(5) . . ?
C14 C13 C18 117.1(6) . . ?
C18 C13 C1 124.4(6) . . ?
C13 C14 H14 118.2 . . ?
C13 C14 C15 123.7(6) . . ?
C15 C14 H14 118.2 . . ?
C14 C15 C19 122.2(5) . . ?
C16 C15 C14 116.2(6) . . ?
C16 C15 C19 121.6(6) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(7) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 118.8 . . ?
C18 C17 C16 122.5(6) . . ?
C18 C17 H17 118.8 . . ?
O4 C18 C13 116.9(6) . . ?
C17 C18 O4 123.2(6) . . ?
C17 C18 C13 119.9(7) . . ?
C20 C19 C15 122.0(6) . . ?
C24 C19 C15 121.1(6) . . ?
C24 C19 C20 116.9(7) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.4(7) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.9(7) . . ?
C22 C21 H21 119.6 . . ?
O3 C22 C23 116.8(8) . . ?
C21 C22 O3 123.4(7) . . ?
C21 C22 C23 119.8(7) . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.3(7) . . ?
C24 C23 H23 120.3 . . ?
C19 C24 C23 121.6(7) . . ?
C19 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C10' O1' H1O' 109.5 . . ?
C6' O2' H2O' 109.5 . . ?
C22' O3' H3O' 109.5 . . ?
C18' O4' H4O' 109.5 . . ?
C2' C1' C6' 116.8(6) . . ?
C2' C1' C13' 119.4(5) . . ?
C6' C1' C13' 123.6(7) . . ?
C1' C2' H2'A 117.8 . . ?
C3' C2' C1' 124.3(6) . . ?
C3' C2' H2'A 117.8 . . ?
C2' C3' C4' 116.5(7) . . ?
C2' C3' C7' 121.5(6) . . ?
C4' C3' C7' 121.9(7) . . ?
C3' C4' H4'A 119.6 . . ?
C5' C4' C3' 120.8(7) . . ?
C5' C4' H4'A 119.6 . . ?
C4' C5' H5' 118.9 . . ?
C4' C5' C6' 122.2(6) . . ?
C6' C5' H5' 118.9 . . ?
O2' C6' C1' 122.3(7) . . ?
O2' C6' C5' 118.4(7) . . ?
C5' C6' C1' 119.2(7) . . ?
C8' C7' C3' 122.7(6) . . ?
C8' C7' C12' 116.8(8) . . ?
C12' C7' C3' 120.5(7) . . ?
C7' C8' H8' 118.8 . . ?
C7' C8' C9' 122.4(7) . . ?
C9' C8' H8' 118.8 . . ?
C8' C9' H9' 120.5 . . ?
C8' C9' C10' 119.0(8) . . ?
C10' C9' H9' 120.5 . . ?
O1' C10' C9' 116.3(9) . . ?
C11' C10' O1' 124.4(8) . . ?
C11' C10' C9' 119.3(8) . . ?
C10' C11' H11' 119.7 . . ?
C12' C11' C10' 120.6(7) . . ?
C12' C11' H11' 119.7 . . ?
C7' C12' H12' 119.1 . . ?
C11' C12' C7' 121.9(8) . . ?
C11' C12' H12' 119.1 . . ?
C14' C13' C1' 119.5(5) . . ?
C14' C13' C18' 117.4(6) . . ?
C18' C13' C1' 122.7(6) . . ?
C13' C14' H14' 118.6 . . ?
C15' C14' C13' 122.9(5) . . ?
C15' C14' H14' 118.6 . . ?
C14' C15' C16' 117.7(6) . . ?
C14' C15' C19' 120.7(6) . . ?
C16' C15' C19' 121.6(6) . . ?
C15' C16' H16' 119.7 . . ?
C17' C16' C15' 120.7(7) . . ?
C17' C16' H16' 119.7 . . ?
C16' C17' H17' 119.9 . . ?
C18' C17' C16' 120.1(6) . . ?
C18' C17' H17' 119.9 . . ?
O4' C18' C13' 118.1(7) . . ?
O4' C18' C17' 120.9(6) . . ?
C17' C18' C13' 121.0(7) . . ?
C20' C19' C15' 123.8(6) . . ?
C20' C19' C24' 116.9(7) . . ?
C24' C19' C15' 119.1(6) . . ?
C19' C20' H20' 118.3 . . ?
C19' C20' C21' 123.5(7) . . ?
C21' C20' H20' 118.3 . . ?
C20' C21' H21' 120.8 . . ?
C20' C21' C22' 118.5(7) . . ?
C22' C21' H21' 120.8 . . ?
O3' C22' C21' 121.1(7) . . ?
C23' C22' O3' 119.2(7) . . ?
C23' C22' C21' 119.6(7) . . ?
C22' C23' H23' 119.9 . . ?
C22' C23' C24' 120.2(7) . . ?
C24' C23' H23' 119.9 . . ?
C19' C24' H24' 119.4 . . ?
C23' C24' C19' 121.3(7) . . ?
C23' C24' H24' 119.4 . . ?
H1AA C1AC H1AB 109.5 . . ?
H1AA C1AC H1AC 109.5 . . ?
H1AB C1AC H1AC 109.5 . . ?
C2AC C1AC H1AA 109.5 . . ?
C2AC C1AC H1AB 109.5 . . ?
C2AC C1AC H1AC 109.5 . . ?
O1AC C2AC C1AC 121.1(16) . . ?
O1AC C2AC C3AC 120.8(14) . . ?
C1AC C2AC C3AC 118.0(17) . . ?
C2AC C3AC H3AA 109.5 . . ?
C2AC C3AC H3AB 109.5 . . ?
C2AC C3AC H3AC 109.5 . . ?
H3AA C3AC H3AB 109.5 . . ?
H3AA C3AC H3AC 109.5 . . ?
H3AB C3AC H3AC 109.5 . . ?
H4AA C4AC H4AB 109.5 . . ?
H4AA C4AC H4AC 109.5 . . ?
H4AB C4AC H4AC 109.5 . . ?
C5AC C4AC H4AA 109.5 . . ?
C5AC C4AC H4AB 109.5 . . ?
C5AC C4AC H4AC 109.5 . . ?
O2AC C5AC C4AC 122.0(12) . . ?
O2AC C5AC C6AC 119.8(9) . . ?
C4AC C5AC C6AC 118.1(11) . . ?
C5AC C6AC H6AA 109.5 . . ?
C5AC C6AC H6AB 109.5 . . ?
C5AC C6AC H6AC 109.5 . . ?
H6AA C6AC H6AB 109.5 . . ?
H6AA C6AC H6AC 109.5 . . ?
H6AB C6AC H6AC 109.5 . . ?
H1O5 O5 H2O5 104.5 . . ?
H1O6 O6 H2O6 104.6 . . ?
H2O7 O7 H1O7 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2O O4 0.82 1.90 2.619(8) 145.6 . yes
O3' H3O' O7 0.82 1.83 2.617(12) 159.8 1_644 yes
O6 H1O6 O7 0.85 2.29 2.54(2) 97.1 . yes
O7 H2O7 O6 0.85 1.74 2.54(2) 156.0 . yes

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
O1 C10 C11 C12 -179.4(8) . . . . ?
O3 C22 C23 C24 -179.5(8) . . . . ?
C1 C2 C3 C4 2.6(9) . . . . ?
C1 C2 C3 C7 -176.0(5) . . . . ?
C1 C13 C14 C15 176.4(5) . . . . ?
C1 C13 C18 O4 2.2(8) . . . . ?
C1 C13 C18 C17 -177.7(6) . . . . ?
C2 C1 C6 O2 178.4(6) . . . . ?
C2 C1 C6 C5 0.6(9) . . . . ?
C2 C1 C13 C14 -39.8(8) . . . . ?
C2 C1 C13 C18 135.6(6) . . . . ?
C2 C3 C4 C5 -1.0(10) . . . . ?
C2 C3 C7 C8 -20.2(9) . . . . ?
C2 C3 C7 C12 157.4(6) . . . . ?
C3 C4 C5 C6 -0.6(12) . . . . ?
C3 C7 C8 C9 178.4(7) . . . . ?
C3 C7 C12 C11 179.6(7) . . . . ?
C4 C3 C7 C8 161.3(7) . . . . ?
C4 C3 C7 C12 -21.1(10) . . . . ?
C4 C5 C6 O2 -177.1(7) . . . . ?
C4 C5 C6 C1 0.8(12) . . . . ?
C6 C1 C2 C3 -2.4(8) . . . . ?
C6 C1 C13 C14 138.3(6) . . . . ?
C6 C1 C13 C18 -46.3(8) . . . . ?
C7 C3 C4 C5 177.6(7) . . . . ?
C7 C8 C9 C10 1.0(13) . . . . ?
C8 C7 C12 C11 -2.6(12) . . . . ?
C8 C9 C10 O1 177.6(8) . . . . ?
C8 C9 C10 C11 -0.9(13) . . . . ?
C9 C10 C11 C12 -0.9(13) . . . . ?
C10 C11 C12 C7 2.8(14) . . . . ?
C12 C7 C8 C9 0.7(11) . . . . ?
C13 C1 C2 C3 175.8(5) . . . . ?
C13 C1 C6 O2 0.3(9) . . . . ?
C13 C1 C6 C5 -177.5(6) . . . . ?
C13 C14 C15 C16 0.1(9) . . . . ?
C13 C14 C15 C19 -177.7(6) . . . . ?
C14 C13 C18 O4 177.7(5) . . . . ?
C14 C13 C18 C17 -2.3(9) . . . . ?
C14 C15 C16 C17 0.7(11) . . . . ?
C14 C15 C19 C20 -17.1(9) . . . . ?
C14 C15 C19 C24 162.2(7) . . . . ?
C15 C16 C17 C18 -2.4(12) . . . . ?
C15 C19 C20 C21 179.3(7) . . . . ?
C15 C19 C24 C23 179.4(7) . . . . ?
C16 C15 C19 C20 165.2(7) . . . . ?
C16 C15 C19 C24 -15.4(10) . . . . ?
C16 C17 C18 O4 -176.7(7) . . . . ?
C16 C17 C18 C13 3.2(11) . . . . ?
C18 C13 C14 C15 0.7(9) . . . . ?
C19 C15 C16 C17 178.5(7) . . . . ?
C19 C20 C21 C22 2.1(12) . . . . ?
C20 C19 C24 C23 -1.2(11) . . . . ?
C20 C21 C22 O3 178.1(8) . . . . ?
C20 C21 C22 C23 -2.6(13) . . . . ?
C21 C22 C23 C24 1.3(13) . . . . ?
C22 C23 C24 C19 0.7(13) . . . . ?
C24 C19 C20 C21 -0.1(11) . . . . ?
O1' C10' C11' C12' 179.1(8) . . . . ?
O3' C22' C23' C24' -178.3(8) . . . . ?
C1' C2' C3' C4' 2.4(10) . . . . ?
C1' C2' C3' C7' -175.5(6) . . . . ?
C1' C13' C14' C15' 175.0(6) . . . . ?
C1' C13' C18' O4' 3.4(10) . . . . ?
C1' C13' C18' C17' -178.7(7) . . . . ?
C2' C1' C6' O2' 175.0(7) . . . . ?
C2' C1' C6' C5' -1.2(11) . . . . ?
C2' C1' C13' C14' -39.1(9) . . . . ?
C2' C1' C13' C18' 134.2(7) . . . . ?
C2' C3' C4' C5' -0.8(12) . . . . ?
C2' C3' C7' C8' -28.7(10) . . . . ?
C2' C3' C7' C12' 147.7(7) . . . . ?
C3' C4' C5' C6' -1.8(13) . . . . ?
C3' C7' C8' C9' 176.1(8) . . . . ?
C3' C7' C12' C11' -175.7(7) . . . . ?
C4' C3' C7' C8' 153.6(8) . . . . ?
C4' C3' C7' C12' -30.1(11) . . . . ?
C4' C5' C6' O2' -173.6(8) . . . . ?
C4' C5' C6' C1' 2.8(13) . . . . ?
C6' C1' C2' C3' -1.5(10) . . . . ?
C6' C1' C13' C14' 135.3(7) . . . . ?
C6' C1' C13' C18' -51.4(10) . . . . ?
C7' C3' C4' C5' 177.1(8) . . . . ?
C7' C8' C9' C10' 0.3(14) . . . . ?
C8' C7' C12' C11' 0.9(12) . . . . ?
C8' C9' C10' O1' -178.7(8) . . . . ?
C8' C9' C10' C11' -0.9(14) . . . . ?
C9' C10' C11' C12' 1.4(13) . . . . ?
C10' C11' C12' C7' -1.5(13) . . . . ?
C12' C7' C8' C9' -0.3(12) . . . . ?
C13' C1' C2' C3' 173.3(6) . . . . ?
C13' C1' C6' O2' 0.5(12) . . . . ?
C13' C1' C6' C5' -175.7(7) . . . . ?
C13' C14' C15' C16' 3.1(10) . . . . ?
C13' C14' C15' C19' -175.8(6) . . . . ?
C14' C13' C18' O4' 176.9(6) . . . . ?
C14' C13' C18' C17' -5.3(11) . . . . ?
C14' C15' C16' C17' -3.7(11) . . . . ?
C14' C15' C19' C20' -30.4(10) . . . . ?
C14' C15' C19' C24' 145.0(7) . . . . ?
C15' C16' C17' C18' -0.2(13) . . . . ?
C15' C19' C20' C21' 174.6(7) . . . . ?
C15' C19' C24' C23' -174.4(7) . . . . ?
C16' C15' C19' C20' 150.7(8) . . . . ?
C16' C15' C19' C24' -33.8(10) . . . . ?
C16' C17' C18' O4' -177.4(8) . . . . ?
C16' C17' C18' C13' 4.8(12) . . . . ?
C18' C13' C14' C15' 1.3(10) . . . . ?
C19' C15' C16' C17' 175.2(7) . . . . ?
C19' C20' C21' C22' 0.3(13) . . . . ?
C20' C19' C24' C23' 1.4(11) . . . . ?
C20' C21' C22' O3' 178.8(7) . . . . ?
C20' C21' C22' C23' -0.2(12) . . . . ?
C21' C22' C23' C24' 0.7(12) . . . . ?
C22' C23' C24' C19' -1.3(12) . . . . ?
C24' C19' C20' C21' -0.9(11) . . . . ?

_olex2_exptl_crystal_mounting_method oil
_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 2.263
_oxdiff_exptl_absorpt_empirical_full_min 0.238
