# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_eze1s
_database_code_depnum_ccdc_archive 'CCDC 1980178'
loop_
_audit_author_name
_audit_author_address
'Hemant Yennawar'
;The Pennsylvania State University
United States of America
;
_audit_update_record             
;
2020-02-12 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_audit_creation_date             2020-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
mcg45@psu.edu
'su339@psu.edu '
cberic.@hotmail.com
srh5411@psu.edu
tuw169@psu.edu
smo5456@psu.edu
rh34@cornell.edu
vhc2@psu.edu
jvb2@psu.edu
eze31@psu.edu
_chemical_name_common            ?
_chemical_name_systematic        'Phenol Pentafluorophenol'
_chemical_formula_moiety         '3(C6 H F5 O), 3(C6 H6 O)'
_chemical_formula_sum            'C36 H21 F15 O6'
_chemical_formula_weight         834.53
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   7.4348(6)
_cell_length_b                   23.1324(18)
_cell_length_c                   20.2671(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.3770(10)
_cell_angle_gamma                90
_cell_volume                     3485.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4629
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.177
_cell_measurement_theta_min      2.672
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.345906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V2.05 (BRUKER, 2001) was used for absorption correction.
R(int) was 0.0631 before and 0.0331 after correction.
The Ratio of minimum to maximum transmission is 0.3459.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (5 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 5.82 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12695
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.761
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.975
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                4844
_reflns_number_total             6051
_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       'SAINT V6.36A (BRUKER, 2001)'
_computing_data_collection       'SMART V5.634 (Bruker Inc., 2009)'
_computing_data_reduction        'SAINT V6.36A (BRUKER, 2001)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 1972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(3)
_refine_ls_extinction_coef       0.0070(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     521
_refine_ls_number_reflns         6051
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.027
_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)+(0.0449P)²+0.0105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0876
_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:
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
 C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O2(H2), O5(H5), O6(H6)
;
_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 0.0011(4) 0.68820(11) 0.67208(11) 0.0802(7) Uani 1 1 d . . . . .
H1 H -0.034716 0.670137 0.704230 0.120 Uiso 1 1 calc GR . . . .
F2 F 0.0021(3) 0.57026(10) 0.69213(12) 0.0992(7) Uani 1 1 d . . . . .
F3 F 0.1054(5) 0.49761(11) 0.59504(17) 0.1191(9) Uani 1 1 d . . . . .
F4 F 0.2092(3) 0.53963(12) 0.47660(12) 0.1098(9) Uani 1 1 d . . . . .
F5 F 0.2208(4) 0.65607(13) 0.45789(11) 0.1065(8) Uani 1 1 d . . . . .
F1 F 0.1162(4) 0.72825(10) 0.55438(12) 0.1019(7) Uani 1 1 d . . . . .
C1 C 0.1130(5) 0.67088(15) 0.56481(16) 0.0652(8) Uani 1 1 d . . . . .
C2 C 0.0548(4) 0.65062(15) 0.62481(16) 0.0620(8) Uani 1 1 d . . . . .
C3 C 0.0550(5) 0.59172(16) 0.63403(17) 0.0684(9) Uani 1 1 d . . . . .
C4 C 0.1076(6) 0.55468(16) 0.5845(2) 0.0745(9) Uani 1 1 d . . . . .
C5 C 0.1616(5) 0.57605(19) 0.52526(19) 0.0749(10) Uani 1 1 d . . . . .
C6 C 0.1648(5) 0.63405(18) 0.51543(16) 0.0709(9) Uani 1 1 d . . . . .
F7 F 0.2417(4) 0.30737(12) 0.29598(11) 0.1045(8) Uani 1 1 d . . . . .
F8 F 0.1936(3) 0.25185(9) 0.41187(12) 0.0906(7) Uani 1 1 d . . . . .
O3 O 0.2794(4) 0.30332(13) 0.52837(13) 0.0882(8) Uani 1 1 d . . . . .
H3 H 0.328083 0.321195 0.558526 0.132 Uiso 1 1 calc GR . . . .
F9 F 0.4253(4) 0.41172(10) 0.52544(11) 0.0968(7) Uani 1 1 d . . . . .
F10 F 0.4760(3) 0.46761(9) 0.40956(13) 0.0977(7) Uani 1 1 d . . . . .
F6 F 0.3848(4) 0.41536(12) 0.29443(12) 0.1092(8) Uani 1 1 d . . . . .
C7 C 0.3607(5) 0.38774(16) 0.35190(18) 0.0705(9) Uani 1 1 d . . . . .
C8 C 0.2888(5) 0.33310(17) 0.35302(17) 0.0696(9) Uani 1 1 d . . . . .
C9 C 0.2646(4) 0.30507(14) 0.41127(19) 0.0640(8) Uani 1 1 d . . . . .
C10 C 0.3097(4) 0.33086(15) 0.47046(16) 0.0628(8) Uani 1 1 d . . . . .
C11 C 0.3803(5) 0.38585(15) 0.46807(17) 0.0650(8) Uani 1 1 d . . . . .
C12 C 0.4068(5) 0.41418(14) 0.40989(19) 0.0676(9) Uani 1 1 d . . . . .
F12 F 0.7899(4) 0.43301(12) 0.64758(15) 0.1152(9) Uani 1 1 d . . . . .
F13 F 0.7820(4) 0.47070(10) 0.77449(18) 0.1231(10) Uani 1 1 d . . . . .
F14 F 0.8988(4) 0.39964(13) 0.87273(13) 0.1179(9) Uani 1 1 d . . . . .
F15 F 1.0266(3) 0.29344(10) 0.84369(10) 0.0875(6) Uani 1 1 d . . . . .
O4 O 1.0469(4) 0.25631(10) 0.71756(12) 0.0755(6) Uani 1 1 d . . . . .
H4 H 1.041009 0.250297 0.677733 0.113 Uiso 1 1 calc GR . . . .
F11 F 0.9226(4) 0.32781(12) 0.61944(11) 0.1030(8) Uani 1 1 d . . . . .
C13 C 0.9159(5) 0.34548(16) 0.68256(16) 0.0670(9) Uani 1 1 d . . . . .
C14 C 0.8503(5) 0.39906(16) 0.6962(2) 0.0767(10) Uani 1 1 d . . . . .
C15 C 0.8453(5) 0.41803(16) 0.7600(2) 0.0797(11) Uani 1 1 d . . . . .
C16 C 0.9040(5) 0.38201(17) 0.8097(2) 0.0755(10) Uani 1 1 d . . . . .
C17 C 0.9682(4) 0.32819(16) 0.79527(16) 0.0633(8) Uani 1 1 d . . . . .
C18 C 0.9779(4) 0.30889(14) 0.73096(16) 0.0583(7) Uani 1 1 d . . . . .
O2 O 0.5864(5) 0.71652(11) 0.58867(17) 0.1052(10) Uani 1 1 d . . . . .
H2 H 0.642515 0.732922 0.559444 0.158 Uiso 1 1 calc GR . . . .
C19 C 0.6000(5) 0.65719(13) 0.58043(18) 0.0646(8) Uani 1 1 d . . . . .
C20 C 0.5605(5) 0.62185(17) 0.63284(18) 0.0725(9) Uani 1 1 d . . . . .
H20 H 0.527008 0.637432 0.673231 0.087 Uiso 1 1 calc R . . . .
C21 C 0.5714(5) 0.56351(18) 0.6245(2) 0.0819(11) Uani 1 1 d . . . . .
H21 H 0.545726 0.539143 0.659686 0.098 Uiso 1 1 calc R . . . .
C22 C 0.6196(6) 0.54017(16) 0.5650(2) 0.0831(11) Uani 1 1 d . . . . .
H22 H 0.625984 0.500263 0.559947 0.100 Uiso 1 1 calc R . . . .
C23 C 0.6581(5) 0.57552(17) 0.5135(2) 0.0781(10) Uani 1 1 d . . . . .
H23 H 0.690669 0.559659 0.473160 0.094 Uiso 1 1 calc R . . . .
C24 C 0.6493(5) 0.63473(16) 0.52054(18) 0.0710(9) Uani 1 1 d . . . . .
H24 H 0.676368 0.658989 0.485381 0.085 Uiso 1 1 calc R . . . .
O5 O 0.7775(4) 0.32231(13) 0.28052(13) 0.0876(7) Uani 1 1 d . . . . .
H5 H 0.708412 0.294835 0.283592 0.131 Uiso 1 1 calc GR . . . .
C25 C 0.8098(4) 0.34547(15) 0.34293(16) 0.0618(8) Uani 1 1 d . . . . .
C26 C 0.7869(5) 0.31266(16) 0.39833(18) 0.0702(9) Uani 1 1 d . . . . .
H26 H 0.749081 0.274447 0.394885 0.084 Uiso 1 1 calc R . . . .
C27 C 0.8205(5) 0.3369(2) 0.45953(19) 0.0829(11) Uani 1 1 d . . . . .
H27 H 0.804000 0.314983 0.497487 0.100 Uiso 1 1 calc R . . . .
C28 C 0.8776(6) 0.3927(2) 0.4645(2) 0.0863(12) Uani 1 1 d . . . . .
H28 H 0.901398 0.408804 0.505752 0.104 Uiso 1 1 calc R . . . .
C29 C 0.8997(6) 0.42498(17) 0.4087(2) 0.0832(11) Uani 1 1 d . . . . .
H29 H 0.937580 0.463187 0.412122 0.100 Uiso 1 1 calc R . . . .
C30 C 0.8664(5) 0.40129(16) 0.34719(18) 0.0731(9) Uani 1 1 d . . . . .
H30 H 0.882348 0.423225 0.309225 0.088 Uiso 1 1 calc R . . . .
O6 O 0.4489(5) 0.30810(13) 0.64818(14) 0.1033(9) Uani 1 1 d . . . . .
H6 H 0.480518 0.275683 0.659802 0.155 Uiso 1 1 calc GR . . . .
C31 C 0.4249(5) 0.34230(16) 0.70286(17) 0.0655(8) Uani 1 1 d . . . . .
C32 C 0.3616(6) 0.39730(16) 0.6950(2) 0.0777(10) Uani 1 1 d . . . . .
H32 H 0.335020 0.411432 0.653075 0.093 Uiso 1 1 calc R . . . .
C33 C 0.3377(6) 0.43148(18) 0.7495(3) 0.0924(13) Uani 1 1 d . . . . .
H33 H 0.293526 0.468850 0.744536 0.111 Uiso 1 1 calc R . . . .
C34 C 0.3786(6) 0.4109(2) 0.8118(2) 0.0917(13) Uani 1 1 d . . . . .
H34 H 0.363229 0.434296 0.848631 0.110 Uiso 1 1 calc R . . . .
C35 C 0.4419(6) 0.3557(2) 0.81863(19) 0.0810(11) Uani 1 1 d . . . . .
H35 H 0.469092 0.341518 0.860442 0.097 Uiso 1 1 calc R . . . .
C36 C 0.4657(5) 0.32139(17) 0.76474(19) 0.0720(9) Uani 1 1 d . . . . .
H36 H 0.509329 0.283958 0.769769 0.086 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 H1 0.8200 . ?
O1 C2 1.356(4) . ?
F2 C3 1.339(4) . ?
F3 C4 1.337(4) . ?
F4 C5 1.346(4) . ?
F5 C6 1.341(4) . ?
F1 C1 1.344(4) . ?
C1 C2 1.376(5) . ?
C1 C6 1.371(5) . ?
C2 C3 1.375(5) . ?
C3 C4 1.378(5) . ?
C4 C5 1.362(6) . ?
C5 C6 1.357(6) . ?
F7 C8 1.345(4) . ?
F8 C9 1.340(4) . ?
O3 H3 0.8200 . ?
O3 C10 1.356(4) . ?
F9 C11 1.348(4) . ?
F10 C12 1.339(4) . ?
F6 C7 1.341(4) . ?
C7 C8 1.373(6) . ?
C7 C12 1.367(5) . ?
C8 C9 1.360(5) . ?
C9 C10 1.379(5) . ?
C10 C11 1.377(5) . ?
C11 C12 1.364(5) . ?
F12 C14 1.335(5) . ?
F13 C15 1.339(4) . ?
F14 C16 1.341(5) . ?
F15 C17 1.339(4) . ?
O4 H4 0.8200 . ?
O4 C18 1.348(4) . ?
F11 C13 1.344(4) . ?
C13 C14 1.361(5) . ?
C13 C18 1.373(5) . ?
C14 C15 1.367(6) . ?
C15 C16 1.376(6) . ?
C16 C17 1.366(5) . ?
C17 C18 1.380(5) . ?
O2 H2 0.8200 . ?
O2 C19 1.386(4) . ?
C19 C20 1.374(5) . ?
C19 C24 1.372(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.363(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.358(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.379(5) . ?
C24 H24 0.9300 . ?
O5 H5 0.8200 . ?
O5 C25 1.393(4) . ?
C25 C26 1.367(5) . ?
C25 C30 1.360(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.382(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.364(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.366(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.383(5) . ?
C30 H30 0.9300 . ?
O6 H6 0.8200 . ?
O6 C31 1.374(4) . ?
C31 C32 1.366(5) . ?
C31 C36 1.376(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.372(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.380(7) . ?
C34 H34 0.9300 . ?
C34 C35 1.367(6) . ?
C35 H35 0.9300 . ?
C35 C36 1.363(6) . ?
C36 H36 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
C2 O1 H1 109.5 . . ?
F1 C1 C2 118.8(3) . . ?
F1 C1 C6 119.6(3) . . ?
C6 C1 C2 121.7(3) . . ?
O1 C2 C1 120.1(3) . . ?
O1 C2 C3 122.6(3) . . ?
C3 C2 C1 117.2(3) . . ?
F2 C3 C2 119.1(3) . . ?
F2 C3 C4 119.7(3) . . ?
C2 C3 C4 121.1(3) . . ?
F3 C4 C3 119.6(4) . . ?
F3 C4 C5 120.2(4) . . ?
C5 C4 C3 120.2(3) . . ?
F4 C5 C4 120.0(4) . . ?
F4 C5 C6 120.4(4) . . ?
C6 C5 C4 119.6(3) . . ?
F5 C6 C1 119.3(4) . . ?
F5 C6 C5 120.6(3) . . ?
C5 C6 C1 120.1(3) . . ?
C10 O3 H3 109.5 . . ?
F6 C7 C8 120.5(3) . . ?
F6 C7 C12 120.0(3) . . ?
C12 C7 C8 119.6(3) . . ?
F7 C8 C7 119.5(3) . . ?
F7 C8 C9 120.0(4) . . ?
C9 C8 C7 120.5(3) . . ?
F8 C9 C8 120.0(3) . . ?
F8 C9 C10 118.9(3) . . ?
C8 C9 C10 121.1(3) . . ?
O3 C10 C9 120.6(3) . . ?
O3 C10 C11 122.0(3) . . ?
C11 C10 C9 117.4(3) . . ?
F9 C11 C10 118.2(3) . . ?
F9 C11 C12 119.7(3) . . ?
C12 C11 C10 122.1(3) . . ?
F10 C12 C7 120.2(3) . . ?
F10 C12 C11 120.4(3) . . ?
C11 C12 C7 119.4(3) . . ?
C18 O4 H4 109.5 . . ?
F11 C13 C14 119.0(3) . . ?
F11 C13 C18 118.6(3) . . ?
C14 C13 C18 122.4(3) . . ?
F12 C14 C13 120.4(4) . . ?
F12 C14 C15 119.9(4) . . ?
C13 C14 C15 119.7(3) . . ?
F13 C15 C14 120.7(4) . . ?
F13 C15 C16 120.0(4) . . ?
C14 C15 C16 119.2(3) . . ?
F14 C16 C15 120.1(4) . . ?
F14 C16 C17 119.6(4) . . ?
C17 C16 C15 120.3(3) . . ?
F15 C17 C16 120.2(3) . . ?
F15 C17 C18 118.6(3) . . ?
C16 C17 C18 121.2(3) . . ?
O4 C18 C13 122.6(3) . . ?
O4 C18 C17 120.3(3) . . ?
C13 C18 C17 117.1(3) . . ?
C19 O2 H2 109.5 . . ?
C20 C19 O2 118.7(3) . . ?
C24 C19 O2 120.1(3) . . ?
C24 C19 C20 121.2(3) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.7(4) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(4) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 118.7(3) . . ?
C19 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C25 O5 H5 109.5 . . ?
C26 C25 O5 120.7(3) . . ?
C30 C25 O5 118.3(3) . . ?
C30 C25 C26 121.0(3) . . ?
C25 C26 H26 120.4 . . ?
C25 C26 C27 119.3(3) . . ?
C27 C26 H26 120.4 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.4(4) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.2 . . ?
C27 C28 C29 119.7(4) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.6(4) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 C29 119.1(3) . . ?
C25 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C31 O6 H6 109.5 . . ?
O6 C31 C36 120.2(3) . . ?
C32 C31 O6 119.2(3) . . ?
C32 C31 C36 120.5(3) . . ?
C31 C32 H32 120.4 . . ?
C31 C32 C33 119.3(4) . . ?
C33 C32 H32 120.4 . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.6(4) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 120.4 . . ?
C35 C34 C33 119.2(4) . . ?
C35 C34 H34 120.4 . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.6(4) . . ?
C36 C35 H35 119.7 . . ?
C31 C36 H36 120.1 . . ?
C35 C36 C31 119.8(4) . . ?
C35 C36 H36 120.1 . . ?

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 C2 C3 F2 -0.7(5) . . . . ?
O1 C2 C3 C4 178.9(3) . . . . ?
F2 C3 C4 F3 -0.1(5) . . . . ?
F2 C3 C4 C5 180.0(3) . . . . ?
F3 C4 C5 F4 1.5(5) . . . . ?
F3 C4 C5 C6 -179.4(4) . . . . ?
F4 C5 C6 F5 -2.1(5) . . . . ?
F4 C5 C6 C1 178.8(3) . . . . ?
F1 C1 C2 O1 0.3(5) . . . . ?
F1 C1 C2 C3 -179.4(3) . . . . ?
F1 C1 C6 F5 1.2(5) . . . . ?
F1 C1 C6 C5 -179.8(3) . . . . ?
C1 C2 C3 F2 178.9(3) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C1 C6 F5 -179.9(3) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C2 C3 C4 F3 -179.7(4) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 F4 -178.6(3) . . . . ?
C3 C4 C5 C6 0.6(6) . . . . ?
C4 C5 C6 F5 178.7(3) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C6 C1 C2 O1 -178.7(3) . . . . ?
C6 C1 C2 C3 1.7(5) . . . . ?
F7 C8 C9 F8 -0.1(5) . . . . ?
F7 C8 C9 C10 -179.2(3) . . . . ?
F8 C9 C10 O3 -1.3(5) . . . . ?
F8 C9 C10 C11 -179.2(3) . . . . ?
O3 C10 C11 F9 2.2(5) . . . . ?
O3 C10 C11 C12 -178.4(3) . . . . ?
F9 C11 C12 F10 -0.5(5) . . . . ?
F9 C11 C12 C7 -180.0(3) . . . . ?
F6 C7 C8 F7 -0.2(5) . . . . ?
F6 C7 C8 C9 179.9(3) . . . . ?
F6 C7 C12 F10 0.0(5) . . . . ?
F6 C7 C12 C11 179.4(3) . . . . ?
C7 C8 C9 F8 179.7(3) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C8 C7 C12 F10 -179.6(3) . . . . ?
C8 C7 C12 C11 -0.1(5) . . . . ?
C8 C9 C10 O3 177.8(3) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 F9 -179.9(3) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 F10 -179.9(3) . . . . ?
C10 C11 C12 C7 0.6(5) . . . . ?
C12 C7 C8 F7 179.3(3) . . . . ?
C12 C7 C8 C9 -0.6(5) . . . . ?
F12 C14 C15 F13 -0.7(6) . . . . ?
F12 C14 C15 C16 178.4(4) . . . . ?
F13 C15 C16 F14 -0.3(6) . . . . ?
F13 C15 C16 C17 179.8(3) . . . . ?
F14 C16 C17 F15 -0.5(5) . . . . ?
F14 C16 C17 C18 -179.1(3) . . . . ?
F15 C17 C18 O4 -0.7(5) . . . . ?
F15 C17 C18 C13 179.7(3) . . . . ?
F11 C13 C14 F12 1.4(5) . . . . ?
F11 C13 C14 C15 -178.9(3) . . . . ?
F11 C13 C18 O4 0.7(5) . . . . ?
F11 C13 C18 C17 -179.6(3) . . . . ?
C13 C14 C15 F13 179.7(3) . . . . ?
C13 C14 C15 C16 -1.2(6) . . . . ?
C14 C13 C18 O4 -178.4(3) . . . . ?
C14 C13 C18 C17 1.2(5) . . . . ?
C14 C15 C16 F14 -179.4(3) . . . . ?
C14 C15 C16 C17 0.7(6) . . . . ?
C15 C16 C17 F15 179.4(3) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C16 C17 C18 O4 177.9(3) . . . . ?
C16 C17 C18 C13 -1.7(5) . . . . ?
C18 C13 C14 F12 -179.4(3) . . . . ?
C18 C13 C14 C15 0.2(6) . . . . ?
O2 C19 C20 C21 179.1(4) . . . . ?
O2 C19 C24 C23 -178.7(4) . . . . ?
C19 C20 C21 C22 -0.4(6) . . . . ?
C20 C19 C24 C23 0.3(5) . . . . ?
C20 C21 C22 C23 0.3(6) . . . . ?
C21 C22 C23 C24 0.1(6) . . . . ?
C22 C23 C24 C19 -0.4(6) . . . . ?
C24 C19 C20 C21 0.1(6) . . . . ?
O5 C25 C26 C27 179.8(3) . . . . ?
O5 C25 C30 C29 -179.8(4) . . . . ?
C25 C26 C27 C28 -0.7(6) . . . . ?
C26 C25 C30 C29 -0.4(5) . . . . ?
C26 C27 C28 C29 0.7(6) . . . . ?
C27 C28 C29 C30 -0.6(6) . . . . ?
C28 C29 C30 C25 0.5(6) . . . . ?
C30 C25 C26 C27 0.5(5) . . . . ?
O6 C31 C32 C33 -180.0(4) . . . . ?
O6 C31 C36 C35 179.8(4) . . . . ?
C31 C32 C33 C34 0.6(6) . . . . ?
C32 C31 C36 C35 0.3(6) . . . . ?
C32 C33 C34 C35 -0.6(6) . . . . ?
C33 C34 C35 C36 0.4(6) . . . . ?
C34 C35 C36 C31 -0.3(6) . . . . ?
C36 C31 C32 C33 -0.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_STRVA01_eze1s               
;
PROBLEM: Chirality of atom sites is inverted?
RESPONSE: Directionality of the hydrogen-bonding pattern was resolved 
at 4 K using powder neutron diffraction data. At 4 K, the H-atom 
of each hyroxyl group is disordered between two postions to generate 
clockwise and anticlockwise directionality in the hydrogen-bonding pattern.
See CCDC structure name UKEKAW.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes'
