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#$Date: 2025-07-06 17:10:52 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/42/1574269.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1574269
loop_
_publ_author_name
'Trevisan, Lucia'
'Bond, Andrew D.'
'Hunter, Christopher A.'
_publ_section_title
;
 Relationship between interaction geometry and cooperativity measured in
 H-bonded networks of hydroxyl groups
;
_journal_issue                   17
_journal_name_full               'Chemical Science'
_journal_page_first              7418
_journal_page_last               7423
_journal_paper_doi               10.1039/D5SC00784D
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C11 H15 F O2'
_chemical_formula_sum            'C11 H15 F O2'
_chemical_formula_weight         198.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2025-01-27 deposited with the CCDC.	2025-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                100.253(6)
_cell_angle_beta                 98.746(6)
_cell_angle_gamma                100.247(6)
_cell_formula_units_Z            6
_cell_length_a                   6.5600(11)
_cell_length_b                   14.795(3)
_cell_length_c                   17.736(3)
_cell_measurement_reflns_used    1480
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      50.61
_cell_measurement_theta_min      2.58
_cell_volume                     1636.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1999
_diffrn_reflns_av_unetI/netI     0.1942
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15674
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        54.170
_diffrn_reflns_theta_max         54.170
_diffrn_reflns_theta_min         2.578
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.5207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       needle
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0077(9)
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         3889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.2263
_refine_ls_R_factor_gt           0.0986
_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)+(0.0973P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.2314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1525
_reflns_number_total             3889
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc00784d2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 1574269--1574270.cif.'
_cod_database_code               1574269
_cambridge_user_name             'Lucia Trevisan'
_cambridge_user_crsid            lt459
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             LT-224
_cambridge_data_id               CH_B1_0050
_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.
;
_shelx_estimated_absorpt_t_min   0.802
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
F1A F 1.2767(7) 0.9965(3) 0.4138(2) 0.0925(15) Uani 1 1 d . . . . .
O1A O 0.6974(8) 0.7409(3) 0.5028(3) 0.0846(16) Uani 1 1 d . . . . .
H1A H 0.595396 0.719420 0.465267 0.127 Uiso 1 1 d R U . . .
O2A O 0.4795(7) 0.7177(4) 0.3513(3) 0.0858(17) Uani 1 1 d . . . . .
H2A H 0.556021 0.711003 0.316960 0.129 Uiso 1 1 d R U . . .
C1A C 0.8467(12) 0.8071(5) 0.4820(4) 0.069(2) Uani 1 1 d . . . . .
C2A C 0.7833(12) 0.8441(5) 0.4176(4) 0.069(2) Uani 1 1 d . . . . .
C3A C 0.9317(14) 0.9083(5) 0.3940(4) 0.075(2) Uani 1 1 d . . . . .
H3A H 0.894088 0.933236 0.349266 0.090 Uiso 1 1 calc R U . . .
C4A C 1.1298(13) 0.9337(5) 0.4365(5) 0.075(2) Uani 1 1 d . . . . .
C5A C 1.1906(12) 0.8995(5) 0.5011(5) 0.073(2) Uani 1 1 d . . . . .
H5A H 1.331895 0.919881 0.529000 0.088 Uiso 1 1 calc R U . . .
C6A C 1.0490(13) 0.8350(5) 0.5271(4) 0.066(2) Uani 1 1 d . . . . .
C7A C 1.1155(12) 0.7970(6) 0.5999(5) 0.075(2) Uani 1 1 d . . . . .
C8A C 1.3430(12) 0.8448(6) 0.6409(4) 0.096(3) Uani 1 1 d . . . . .
H8A H 1.352162 0.912420 0.658041 0.143 Uiso 1 1 calc R U . . .
H8B H 1.439044 0.834658 0.604436 0.143 Uiso 1 1 calc R U . . .
H8C H 1.382547 0.817936 0.686217 0.143 Uiso 1 1 calc R U . . .
C9A C 1.1030(13) 0.6908(6) 0.5785(4) 0.091(3) Uani 1 1 d . . . . .
H9A H 0.959040 0.658927 0.552207 0.137 Uiso 1 1 calc R U . . .
H9B H 1.140433 0.667550 0.626076 0.137 Uiso 1 1 calc R U . . .
H9C H 1.201425 0.677930 0.543572 0.137 Uiso 1 1 calc R U . . .
C10A C 0.9711(13) 0.8182(5) 0.6588(4) 0.092(3) Uani 1 1 d . . . . .
H10A H 0.825844 0.784617 0.636169 0.138 Uiso 1 1 calc R U . . .
H10B H 0.976198 0.885933 0.671093 0.138 Uiso 1 1 calc R U . . .
H10C H 1.019476 0.797567 0.706732 0.138 Uiso 1 1 calc R U . . .
C11A C 0.5573(12) 0.8192(5) 0.3767(4) 0.082(2) Uani 1 1 d . . . . .
H11A H 0.469571 0.845158 0.412261 0.098 Uiso 1 1 calc R U . . .
H11B H 0.543170 0.848520 0.330613 0.098 Uiso 1 1 calc R U . . .
F1B F -0.1091(7) 0.5797(3) 0.0313(2) 0.0978(15) Uani 1 1 d . . . . .
O1B O 0.6097(8) 0.8344(3) 0.1827(2) 0.0864(17) Uani 1 1 d . . . . .
H1B H 0.695895 0.807256 0.205023 0.130 Uiso 1 1 d R U . . .
O2B O 0.7237(7) 0.6965(3) 0.2435(3) 0.0805(16) Uani 1 1 d . . . . .
H2B H 0.846367 0.686625 0.252587 0.121 Uiso 1 1 d R U . . .
C1B C 0.4268(12) 0.7690(6) 0.1458(4) 0.070(2) Uani 1 1 d . . . . .
C2B C 0.4190(12) 0.6731(6) 0.1408(4) 0.067(2) Uani 1 1 d . . . . .
C3B C 0.2329(13) 0.6091(5) 0.1020(4) 0.072(2) Uani 1 1 d . . . . .
H3B H 0.222537 0.543421 0.097779 0.086 Uiso 1 1 calc R U . . .
C4B C 0.0697(13) 0.6423(7) 0.0710(4) 0.078(3) Uani 1 1 d . . . . .
C5B C 0.0740(12) 0.7359(6) 0.0752(4) 0.076(2) Uani 1 1 d . . . . .
H5B H -0.045816 0.755197 0.051204 0.091 Uiso 1 1 calc R U . . .
C6B C 0.2528(13) 0.8029(6) 0.1145(4) 0.070(2) Uani 1 1 d . . . . .
C7B C 0.2564(13) 0.9087(6) 0.1233(4) 0.082(2) Uani 1 1 d . . . . .
C8B C 0.0487(14) 0.9255(5) 0.0813(4) 0.105(3) Uani 1 1 d . . . . .
H8D H 0.025429 0.896163 0.025739 0.157 Uiso 1 1 calc R U . . .
H8E H 0.056120 0.993197 0.087128 0.157 Uiso 1 1 calc R U . . .
H8F H -0.068114 0.897860 0.104098 0.157 Uiso 1 1 calc R U . . .
C9B C 0.2827(13) 0.9554(5) 0.2106(4) 0.102(3) Uani 1 1 d . . . . .
H9D H 0.162849 0.927053 0.231578 0.154 Uiso 1 1 calc R U . . .
H9E H 0.287935 1.022905 0.215747 0.154 Uiso 1 1 calc R U . . .
H9F H 0.413878 0.945868 0.239603 0.154 Uiso 1 1 calc R U . . .
C10B C 0.4344(14) 0.9587(6) 0.0889(5) 0.105(3) Uani 1 1 d . . . . .
H10D H 0.430697 0.923669 0.036188 0.158 Uiso 1 1 calc R U . . .
H10E H 0.570636 0.961806 0.121967 0.158 Uiso 1 1 calc R U . . .
H10F H 0.415629 1.022456 0.086716 0.158 Uiso 1 1 calc R U . . .
C11B C 0.6104(13) 0.6378(5) 0.1697(4) 0.091(3) Uani 1 1 d . . . . .
H11C H 0.567146 0.572497 0.176229 0.109 Uiso 1 1 calc R U . . .
H11D H 0.704033 0.637652 0.130917 0.109 Uiso 1 1 calc R U . . .
F1C F 0.3382(9) 0.4306(3) 0.3854(3) 0.1172(17) Uani 1 1 d . . . . .
O1C O 0.9404(8) 0.4567(3) 0.2043(3) 0.0883(17) Uani 1 1 d . . . . .
H1C H 1.014825 0.511347 0.214762 0.132 Uiso 1 1 d R U . . .
O2C O 1.0725(7) 0.6350(3) 0.2912(3) 0.0874(17) Uani 1 1 d . . . . .
H2C H 1.178410 0.678877 0.309419 0.131 Uiso 1 1 d R U . . .
C1C C 0.7888(13) 0.4521(5) 0.2504(5) 0.069(2) Uani 1 1 d . . . . .
C2C C 0.8215(14) 0.5136(5) 0.3216(5) 0.074(2) Uani 1 1 d . . . . .
C3C C 0.6699(16) 0.5078(6) 0.3672(5) 0.082(2) Uani 1 1 d . . . . .
H3C H 0.688443 0.550351 0.415892 0.098 Uiso 1 1 calc R U . . .
C4C C 0.4876(15) 0.4374(6) 0.3396(6) 0.081(2) Uani 1 1 d . . . . .
C5C C 0.4540(14) 0.3774(6) 0.2691(6) 0.087(3) Uani 1 1 d . . . . .
H5C H 0.325186 0.332145 0.252131 0.104 Uiso 1 1 calc R U . . .
C6C C 0.6029(14) 0.3806(5) 0.2214(5) 0.074(2) Uani 1 1 d . . . . .
C7C C 0.5648(13) 0.3123(6) 0.1419(4) 0.079(2) Uani 1 1 d . . . . .
C8C C 0.3523(12) 0.2410(5) 0.1246(4) 0.103(3) Uani 1 1 d . . . . .
H8G H 0.236281 0.274551 0.122121 0.155 Uiso 1 1 calc R U . . .
H8H H 0.347093 0.205355 0.166085 0.155 Uiso 1 1 calc R U . . .
H8I H 0.338689 0.197689 0.074470 0.155 Uiso 1 1 calc R U . . .
C9C C 0.5602(14) 0.3680(6) 0.0763(4) 0.106(3) Uani 1 1 d . . . . .
H9G H 0.442845 0.400787 0.076212 0.158 Uiso 1 1 calc R U . . .
H9H H 0.541543 0.324702 0.025863 0.158 Uiso 1 1 calc R U . . .
H9J H 0.693419 0.414061 0.085022 0.158 Uiso 1 1 calc R U . . .
C10C C 0.7403(13) 0.2549(6) 0.1393(4) 0.101(3) Uani 1 1 d . . . . .
H10G H 0.878233 0.297925 0.149652 0.151 Uiso 1 1 calc R U . . .
H10H H 0.717755 0.213916 0.087537 0.151 Uiso 1 1 calc R U . . .
H10I H 0.735911 0.216557 0.178945 0.151 Uiso 1 1 calc R U . . .
C11C C 1.0234(12) 0.5851(5) 0.3519(4) 0.087(3) Uani 1 1 d . . . . .
H11E H 1.008901 0.629995 0.398277 0.104 Uiso 1 1 calc R U . . .
H11F H 1.139232 0.553529 0.367541 0.104 Uiso 1 1 calc R U . . .
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A H1A 109.5 . . ?
C11A O2A H2A 95.0 . . ?
C6A C1A C2A 122.9(8) . . ?
C6A C1A O1A 119.2(7) . . ?
C2A C1A O1A 117.9(7) . . ?
C1A C2A C3A 119.0(7) . . ?
C1A C2A C11A 120.4(8) . . ?
C3A C2A C11A 120.5(8) . . ?
C4A C3A C2A 118.2(7) . . ?
C4A C3A H3A 120.9 . . ?
C2A C3A H3A 120.9 . . ?
C3A C4A C5A 122.8(8) . . ?
C3A C4A F1A 118.7(8) . . ?
C5A C4A F1A 118.5(7) . . ?
C4A C5A C6A 121.4(7) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A H5A 119.3 . . ?
C1A C6A C5A 115.6(7) . . ?
C1A C6A C7A 122.7(7) . . ?
C5A C6A C7A 121.6(7) . . ?
C6A C7A C9A 110.8(6) . . ?
C6A C7A C8A 111.3(6) . . ?
C9A C7A C8A 108.2(7) . . ?
C6A C7A C10A 109.6(7) . . ?
C9A C7A C10A 109.7(6) . . ?
C8A C7A C10A 107.2(6) . . ?
C7A C8A H8A 109.5 . . ?
C7A C8A H8B 109.5 . . ?
H8A C8A H8B 109.5 . . ?
C7A C8A H8C 109.5 . . ?
H8A C8A H8C 109.5 . . ?
H8B C8A H8C 109.5 . . ?
C7A C9A H9A 109.5 . . ?
C7A C9A H9B 109.5 . . ?
H9A C9A H9B 109.5 . . ?
C7A C9A H9C 109.5 . . ?
H9A C9A H9C 109.5 . . ?
H9B C9A H9C 109.5 . . ?
C7A C10A H10A 109.5 . . ?
C7A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C7A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
O2A C11A C2A 112.1(6) . . ?
O2A C11A H11A 109.2 . . ?
C2A C11A H11A 109.2 . . ?
O2A C11A H11B 109.2 . . ?
C2A C11A H11B 109.2 . . ?
H11A C11A H11B 107.9 . . ?
C1B O1B H1B 109.4 . . ?
C11B O2B H2B 109.6 . . ?
O1B C1B C2B 120.3(8) . . ?
O1B C1B C6B 117.7(8) . . ?
C2B C1B C6B 122.0(7) . . ?
C1B C2B C3B 118.7(8) . . ?
C1B C2B C11B 121.2(7) . . ?
C3B C2B C11B 119.9(8) . . ?
C4B C3B C2B 118.6(7) . . ?
C4B C3B H3B 120.7 . . ?
C2B C3B H3B 120.7 . . ?
C3B C4B F1B 118.5(8) . . ?
C3B C4B C5B 123.6(7) . . ?
F1B C4B C5B 117.9(8) . . ?
C4B C5B C6B 120.4(8) . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B H5B 119.8 . . ?
C5B C6B C1B 116.6(7) . . ?
C5B C6B C7B 121.1(8) . . ?
C1B C6B C7B 122.3(7) . . ?
C10B C7B C8B 107.2(7) . . ?
C10B C7B C6B 112.0(7) . . ?
C8B C7B C6B 111.2(6) . . ?
C10B C7B C9B 109.3(7) . . ?
C8B C7B C9B 107.0(7) . . ?
C6B C7B C9B 110.0(6) . . ?
C7B C8B H8D 109.5 . . ?
C7B C8B H8E 109.5 . . ?
H8D C8B H8E 109.5 . . ?
C7B C8B H8F 109.5 . . ?
H8D C8B H8F 109.5 . . ?
H8E C8B H8F 109.5 . . ?
C7B C9B H9D 109.5 . . ?
C7B C9B H9E 109.5 . . ?
H9D C9B H9E 109.5 . . ?
C7B C9B H9F 109.5 . . ?
H9D C9B H9F 109.5 . . ?
H9E C9B H9F 109.5 . . ?
C7B C10B H10D 109.5 . . ?
C7B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C7B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
O2B C11B C2B 110.6(6) . . ?
O2B C11B H11C 109.5 . . ?
C2B C11B H11C 109.5 . . ?
O2B C11B H11D 109.5 . . ?
C2B C11B H11D 109.5 . . ?
H11C C11B H11D 108.1 . . ?
C1C O1C H1C 109.5 . . ?
C11C O2C H2C 109.6 . . ?
O1C C1C C2C 120.6(7) . . ?
O1C C1C C6C 116.7(8) . . ?
C2C C1C C6C 122.7(9) . . ?
C3C C2C C1C 120.0(8) . . ?
C3C C2C C11C 118.8(8) . . ?
C1C C2C C11C 121.2(9) . . ?
C2C C3C C4C 117.8(8) . . ?
C2C C3C H3C 121.1 . . ?
C4C C3C H3C 121.1 . . ?
C5C C4C F1C 119.7(9) . . ?
C5C C4C C3C 122.4(9) . . ?
F1C C4C C3C 117.9(9) . . ?
C4C C5C C6C 121.7(8) . . ?
C4C C5C H5C 119.2 . . ?
C6C C5C H5C 119.2 . . ?
C5C C6C C1C 115.4(8) . . ?
C5C C6C C7C 121.5(8) . . ?
C1C C6C C7C 123.0(9) . . ?
C6C C7C C9C 109.6(6) . . ?
C6C C7C C8C 112.8(7) . . ?
C9C C7C C8C 106.9(6) . . ?
C6C C7C C10C 110.4(6) . . ?
C9C C7C C10C 110.1(7) . . ?
C8C C7C C10C 107.0(7) . . ?
C7C C8C H8G 109.5 . . ?
C7C C8C H8H 109.5 . . ?
H8G C8C H8H 109.5 . . ?
C7C C8C H8I 109.5 . . ?
H8G C8C H8I 109.5 . . ?
H8H C8C H8I 109.5 . . ?
C7C C9C H9G 109.5 . . ?
C7C C9C H9H 109.5 . . ?
H9G C9C H9H 109.5 . . ?
C7C C9C H9J 109.5 . . ?
H9G C9C H9J 109.5 . . ?
H9H C9C H9J 109.5 . . ?
C7C C10C H10G 109.5 . . ?
C7C C10C H10H 109.5 . . ?
H10G C10C H10H 109.5 . . ?
C7C C10C H10I 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 109.5 . . ?
O2C C11C C2C 109.3(6) . . ?
O2C C11C H11E 109.8 . . ?
C2C C11C H11E 109.8 . . ?
O2C C11C H11F 109.8 . . ?
C2C C11C H11F 109.8 . . ?
H11E C11C H11F 108.3 . . ?
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
F1A C4A 1.373(8) . ?
O1A C1A 1.397(8) . ?
O1A H1A 0.8399 . ?
O2A C11A 1.462(7) . ?
O2A H2A 0.8501 . ?
C1A C6A 1.391(9) . ?
C1A C2A 1.392(9) . ?
C2A C3A 1.400(9) . ?
C2A C11A 1.498(9) . ?
C3A C4A 1.352(9) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.368(9) . ?
C5A C6A 1.399(9) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.531(9) . ?
C7A C9A 1.534(10) . ?
C7A C8A 1.539(9) . ?
C7A C10A 1.543(10) . ?
C8A H8A 0.9800 . ?
C8A H8B 0.9800 . ?
C8A H8C 0.9800 . ?
C9A H9A 0.9800 . ?
C9A H9B 0.9800 . ?
C9A H9C 0.9800 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
F1B C4B 1.364(8) . ?
O1B C1B 1.389(7) . ?
O1B H1B 0.8400 . ?
O2B C11B 1.445(7) . ?
O2B H2B 0.8400 . ?
C1B C2B 1.397(9) . ?
C1B C6B 1.404(9) . ?
C2B C3B 1.401(9) . ?
C2B C11B 1.498(9) . ?
C3B C4B 1.340(10) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.367(9) . ?
C5B C6B 1.391(9) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.542(10) . ?
C7B C10B 1.533(10) . ?
C7B C8B 1.533(10) . ?
C7B C9B 1.549(9) . ?
C8B H8D 0.9800 . ?
C8B H8E 0.9800 . ?
C8B H8F 0.9800 . ?
C9B H9D 0.9800 . ?
C9B H9E 0.9800 . ?
C9B H9F 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
F1C C4C 1.366(9) . ?
O1C C1C 1.381(9) . ?
O1C H1C 0.8400 . ?
O2C C11C 1.452(8) . ?
O2C H2C 0.8400 . ?
C1C C2C 1.381(9) . ?
C1C C6C 1.424(9) . ?
C2C C3C 1.374(10) . ?
C2C C11C 1.499(9) . ?
C3C C4C 1.397(10) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.361(10) . ?
C5C C6C 1.386(10) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.538(10) . ?
C7C C9C 1.541(9) . ?
C7C C8C 1.544(9) . ?
C7C C10C 1.549(10) . ?
C8C H8G 0.9800 . ?
C8C H8H 0.9800 . ?
C8C H8I 0.9800 . ?
C9C H9G 0.9800 . ?
C9C H9H 0.9800 . ?
C9C H9J 0.9800 . ?
C10C H10G 0.9800 . ?
C10C H10H 0.9800 . ?
C10C H10I 0.9800 . ?
C11C H11E 0.9900 . ?
C11C H11F 0.9900 . ?
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
O1A H1A O2A 0.84 2.04 2.776(6) 145.7 . yes
O2A H2A O2B 0.85 1.84 2.687(7) 179.4 . yes
O1B H1B O2B 0.84 1.91 2.638(6) 144.2 . yes
O2B H2B O2C 0.84 1.88 2.685(7) 160.0 . yes
O1C H1C O2C 0.84 2.01 2.724(6) 142.3 . yes
O2C H2C O2A 0.84 1.94 2.696(6) 148.4 1_655 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
C6A C1A C2A C3A 3.7(11) . . . . ?
O1A C1A C2A C3A -177.9(7) . . . . ?
C6A C1A C2A C11A -173.3(7) . . . . ?
O1A C1A C2A C11A 5.2(10) . . . . ?
C1A C2A C3A C4A -1.9(11) . . . . ?
C11A C2A C3A C4A 175.0(7) . . . . ?
C2A C3A C4A C5A 0.0(12) . . . . ?
C2A C3A C4A F1A 179.9(6) . . . . ?
C3A C4A C5A C6A 0.2(12) . . . . ?
F1A C4A C5A C6A -179.6(7) . . . . ?
C2A C1A C6A C5A -3.3(11) . . . . ?
O1A C1A C6A C5A 178.2(6) . . . . ?
C2A C1A C6A C7A 177.5(7) . . . . ?
O1A C1A C6A C7A -0.9(11) . . . . ?
C4A C5A C6A C1A 1.4(11) . . . . ?
C4A C5A C6A C7A -179.4(7) . . . . ?
C1A C6A C7A C9A 63.3(10) . . . . ?
C5A C6A C7A C9A -115.8(8) . . . . ?
C1A C6A C7A C8A -176.3(7) . . . . ?
C5A C6A C7A C8A 4.6(10) . . . . ?
C1A C6A C7A C10A -58.0(9) . . . . ?
C5A C6A C7A C10A 122.9(7) . . . . ?
C1A C2A C11A O2A -55.4(9) . . . . ?
C3A C2A C11A O2A 127.7(7) . . . . ?
O1B C1B C2B C3B -179.0(6) . . . . ?
C6B C1B C2B C3B 1.2(11) . . . . ?
O1B C1B C2B C11B -4.4(11) . . . . ?
C6B C1B C2B C11B 175.9(7) . . . . ?
C1B C2B C3B C4B 0.2(11) . . . . ?
C11B C2B C3B C4B -174.5(7) . . . . ?
C2B C3B C4B F1B 178.1(6) . . . . ?
C2B C3B C4B C5B -0.2(12) . . . . ?
C3B C4B C5B C6B -1.2(12) . . . . ?
F1B C4B C5B C6B -179.6(7) . . . . ?
C4B C5B C6B C1B 2.5(11) . . . . ?
C4B C5B C6B C7B -176.9(7) . . . . ?
O1B C1B C6B C5B 177.7(6) . . . . ?
C2B C1B C6B C5B -2.5(11) . . . . ?
O1B C1B C6B C7B -2.9(11) . . . . ?
C2B C1B C6B C7B 176.9(7) . . . . ?
C5B C6B C7B C10B -122.4(8) . . . . ?
C1B C6B C7B C10B 58.2(9) . . . . ?
C5B C6B C7B C8B -2.5(10) . . . . ?
C1B C6B C7B C8B 178.1(7) . . . . ?
C5B C6B C7B C9B 115.9(8) . . . . ?
C1B C6B C7B C9B -63.5(10) . . . . ?
C1B C2B C11B O2B 42.3(10) . . . . ?
C3B C2B C11B O2B -143.1(6) . . . . ?
O1C C1C C2C C3C -179.5(7) . . . . ?
C6C C1C C2C C3C -0.9(11) . . . . ?
O1C C1C C2C C11C -1.5(11) . . . . ?
C6C C1C C2C C11C 177.2(7) . . . . ?
C1C C2C C3C C4C 1.3(11) . . . . ?
C11C C2C C3C C4C -176.7(7) . . . . ?
C2C C3C C4C C5C -2.1(12) . . . . ?
C2C C3C C4C F1C 179.0(7) . . . . ?
F1C C4C C5C C6C -178.8(7) . . . . ?
C3C C4C C5C C6C 2.3(12) . . . . ?
C4C C5C C6C C1C -1.6(11) . . . . ?
C4C C5C C6C C7C 179.7(7) . . . . ?
O1C C1C C6C C5C 179.6(7) . . . . ?
C2C C1C C6C C5C 0.9(11) . . . . ?
O1C C1C C6C C7C -1.6(10) . . . . ?
C2C C1C C6C C7C 179.6(7) . . . . ?
C5C C6C C7C C9C 117.1(8) . . . . ?
C1C C6C C7C C9C -61.6(10) . . . . ?
C5C C6C C7C C8C -1.9(10) . . . . ?
C1C C6C C7C C8C 179.4(7) . . . . ?
C5C C6C C7C C10C -121.6(8) . . . . ?
C1C C6C C7C C10C 59.8(10) . . . . ?
C3C C2C C11C O2C -132.9(7) . . . . ?
C1C C2C C11C O2C 49.1(9) . . . . ?
