#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:53:59 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267084 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/97/1559775.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_1559775
loop_
_publ_author_name
'Navarro-Huerta, Armando'
'Jellen, Marcus J.'
'Arcudia, Jessica'
'Teat, Simon J.'
'Toscano, Rubén A'
'Merino, Gabriel'
'Rodríguez-Molina, Braulio'
_publ_section_title
;
 Tailoring the cavities of hydrogen-bonded amphidynamic crystals using
 weak contacts: towards faster molecular machines.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2181
_journal_page_last               2188
_journal_paper_doi               10.1039/d0sc05899h
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.940(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6763(5)
_cell_length_b                   15.0587(11)
_cell_length_c                   21.4299(15)
_cell_measurement_reflns_used    6890
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      2.34
_cell_volume                     2146.5(3)
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_diffrn_ambient_temperature      301(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker D8 Venture κ-geometry diffractometer'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.339
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       prism
_exptl_crystal_F_000             924
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
_exptl_crystal_size_max          0.413
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.298
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1814
_refine_ls_R_factor_gt           0.0542
_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)+(0.0379P)²+0.3103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2032
_reflns_number_total             4923
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05899h2.cif
_cod_data_source_block           ANH-BRM-2-300K
_cod_depositor_comments
;Adding full bibliography for 1559768--1559785.cif.

 Adding full bibliography for 1559768--1559785.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1559775
_shelx_shelxl_version_number     2018/3
_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   0.958
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
F1 F -0.0199(2) 0.23893(10) 0.15508(7) 0.0777(5) Uani 1 1 d . . . . .
F2 F 0.0358(2) 0.15761(11) 0.40099(8) 0.0911(6) Uani 1 1 d . . . . .
F3 F 1.3919(2) 0.53673(12) 0.42066(7) 0.0921(6) Uani 1 1 d . . . . .
F4 F 0.7748(3) 0.68674(13) 0.52834(8) 0.1071(6) Uani 1 1 d . . . . .
C1 C 0.5466(4) 0.33198(17) 0.14440(11) 0.0594(7) Uani 1 1 d . . . . .
H1 H 0.572690 0.326110 0.102666 0.071 Uiso 1 1 calc R U . . .
C2 C 0.3858(4) 0.28993(17) 0.16676(11) 0.0570(7) Uani 1 1 d . . . . .
H2 H 0.304542 0.254314 0.139651 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3386(3) 0.29854(15) 0.22917(11) 0.0464(6) Uani 1 1 d . . . . .
C4 C 0.4605(3) 0.35209(15) 0.26889(11) 0.0469(6) Uani 1 1 d . . . . .
H4 H 0.429804 0.360247 0.310020 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8317(3) 0.48077(15) 0.33750(11) 0.0472(6) Uani 1 1 d . . . . .
H5 H 0.744196 0.470388 0.368196 0.057 Uiso 1 1 calc R U . . .
C6 C 1.0056(3) 0.52963(15) 0.35168(11) 0.0473(6) Uani 1 1 d . . . . .
C7 C 1.1365(4) 0.54389(16) 0.30493(12) 0.0542(7) Uani 1 1 d . . . . .
H7 H 1.254576 0.575597 0.314729 0.065 Uiso 1 1 calc R U . . .
C8 C 1.0955(4) 0.51246(16) 0.24521(12) 0.0546(7) Uani 1 1 d . . . . .
H8 H 1.183449 0.522827 0.214633 0.066 Uiso 1 1 calc R U . . .
N9 N 0.8453(3) 0.42757(14) 0.17620(10) 0.0575(6) Uani 1 1 d . . . . .
H9 H 0.902(3) 0.4313(15) 0.1402(11) 0.069 Uiso 1 1 d . U . . .
C10 C 0.6699(4) 0.38356(16) 0.18530(11) 0.0492(6) Uani 1 1 d . . . . .
C11 C 0.6278(3) 0.39374(15) 0.24808(10) 0.0431(6) Uani 1 1 d . . . . .
C12 C 0.7882(3) 0.44736(14) 0.27758(10) 0.0429(6) Uani 1 1 d . . . . .
C13 C 0.9201(4) 0.46497(16) 0.23156(11) 0.0487(6) Uani 1 1 d . . . . .
C14 C 0.1697(3) 0.24940(15) 0.25332(12) 0.0479(6) Uani 1 1 d . . . . .
C15 C -0.0023(4) 0.22182(17) 0.21809(13) 0.0573(7) Uani 1 1 d . . . . .
C16 C -0.1587(4) 0.17757(18) 0.24088(16) 0.0695(8) Uani 1 1 d . . . . .
H16 H -0.270858 0.161980 0.214403 0.083 Uiso 1 1 calc R U . . .
C17 C -0.1485(4) 0.15641(18) 0.30310(16) 0.0727(9) Uani 1 1 d . . . . .
H17 H -0.252966 0.126533 0.320096 0.087 Uiso 1 1 calc R U . . .
C18 C 0.0201(4) 0.18074(17) 0.33921(14) 0.0631(8) Uani 1 1 d . . . . .
C19 C 0.1761(4) 0.22594(16) 0.31650(12) 0.0564(7) Uani 1 1 d . . . . .
H19 H 0.287542 0.241196 0.343411 0.068 Uiso 1 1 calc R U . . .
C20 C 1.0456(4) 0.57109(16) 0.41402(11) 0.0505(6) Uani 1 1 d . . . . .
C21 C 0.8926(4) 0.61007(18) 0.44408(12) 0.0589(7) Uani 1 1 d . . . . .
H21 H 0.761743 0.608767 0.425310 0.071 Uiso 1 1 calc R U . . .
C22 C 0.9311(4) 0.65019(18) 0.50062(14) 0.0670(8) Uani 1 1 d . . . . .
C23 C 1.1197(5) 0.65638(19) 0.53056(13) 0.0734(8) Uani 1 1 d . . . . .
H23 H 1.142126 0.685576 0.568764 0.088 Uiso 1 1 calc R U . . .
C24 C 1.2742(5) 0.6181(2) 0.50235(14) 0.0745(8) Uani 1 1 d . . . . .
H24 H 1.404749 0.620408 0.521322 0.089 Uiso 1 1 calc R U . . .
C25 C 1.2348(4) 0.57666(18) 0.44612(13) 0.0613(7) Uani 1 1 d . . . . .
N31 N 0.948(3) 0.4549(10) 0.0508(10) 0.050(3) Uani 0.5 1 d . . P A -1
C31 C 0.8356(18) 0.4336(8) 0.0033(4) 0.109(3) Uani 0.5 1 d . . P A -1
H31A H 0.699631 0.451331 0.010285 0.131 Uiso 0.5 1 calc R U P A -1
H31B H 0.836224 0.369385 -0.000028 0.131 Uiso 0.5 1 calc R U P A -1
C32 C 0.885(2) 0.4726(8) -0.0613(3) 0.109(3) Uani 0.5 1 d . . P A -1
H32A H 0.918050 0.424448 -0.088740 0.130 Uiso 0.5 1 calc R U P A -1
H32B H 0.768095 0.503066 -0.080731 0.130 Uiso 0.5 1 calc R U P A -1
C33 C 0.9313(16) 0.5715(6) 0.0510(3) 0.094(2) Uani 0.5 1 d . . P A -1
H33A H 0.798934 0.588992 0.061953 0.113 Uiso 0.5 1 calc R U P A -1
H33B H 1.029898 0.595331 0.082469 0.113 Uiso 0.5 1 calc R U P A -1
C34 C 0.9680(17) 0.6105(5) -0.0136(3) 0.092(2) Uani 0.5 1 d . . P A -1
H34A H 1.082225 0.650538 -0.010533 0.111 Uiso 0.5 1 calc R U P A -1
H34B H 0.850372 0.642027 -0.031760 0.111 Uiso 0.5 1 calc R U P A -1
C35 C 1.1740(13) 0.4587(8) 0.0388(4) 0.102(3) Uani 0.5 1 d . . P A -1
H35A H 1.245439 0.492940 0.072008 0.123 Uiso 0.5 1 calc R U P A -1
H35B H 1.228184 0.398888 0.040819 0.123 Uiso 0.5 1 calc R U P A -1
C36 C 1.2136(15) 0.4995(8) -0.0240(4) 0.103(3) Uani 0.5 1 d . . P A -1
H36A H 1.293054 0.553226 -0.017852 0.123 Uiso 0.5 1 calc R U P A -1
H36B H 1.285214 0.458028 -0.048590 0.123 Uiso 0.5 1 calc R U P A -1
N32 N 1.014(3) 0.5198(11) -0.0557(10) 0.064(4) Uani 0.5 1 d . . P A -1
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'
N N 0.0061 0.0033 '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'
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 C1 C10 118.6(2) . . ?
C2 C1 H1 120.7 . . ?
C10 C1 H1 120.7 . . ?
C1 C2 C3 122.5(2) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 C14 120.1(2) . . ?
C2 C3 C14 121.8(2) . . ?
C3 C4 C11 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C11 C4 H4 119.6 . . ?
C6 C5 C12 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C12 C5 H5 120.0 . . ?
C5 C6 C7 119.1(2) . . ?
C5 C6 C20 120.3(2) . . ?
C7 C6 C20 120.4(2) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C13 118.3(2) . . ?
C7 C8 H8 120.8 . . ?
C13 C8 H8 120.8 . . ?
C13 N9 C10 109.1(2) . . ?
C13 N9 H9 125.1(16) . . ?
C10 N9 H9 125.8(16) . . ?
N9 C10 C1 130.3(2) . . ?
N9 C10 C11 109.0(2) . . ?
C1 C10 C11 120.6(2) . . ?
C4 C11 C10 119.4(2) . . ?
C4 C11 C12 134.4(2) . . ?
C10 C11 C12 106.2(2) . . ?
C5 C12 C13 119.2(2) . . ?
C5 C12 C11 134.2(2) . . ?
C13 C12 C11 106.6(2) . . ?
N9 C13 C8 129.5(2) . . ?
N9 C13 C12 109.1(2) . . ?
C8 C13 C12 121.4(2) . . ?
C15 C14 C19 114.1(2) . . ?
C15 C14 C3 125.6(2) . . ?
C19 C14 C3 120.3(2) . . ?
C16 C15 F1 116.2(3) . . ?
C16 C15 C14 125.2(3) . . ?
F1 C15 C14 118.6(2) . . ?
C15 C16 C17 119.2(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 F2 118.3(3) . . ?
C17 C18 C19 123.3(3) . . ?
F2 C18 C19 118.4(3) . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C20 C25 114.9(2) . . ?
C21 C20 C6 121.1(2) . . ?
C25 C20 C6 124.0(2) . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 F4 118.4(3) . . ?
C21 C22 C23 123.0(3) . . ?
F4 C22 C23 118.5(3) . . ?
C22 C23 C24 117.6(3) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 F3 117.4(3) . . ?
C24 C25 C20 124.4(3) . . ?
F3 C25 C20 118.3(3) . . ?
C31 N31 C35 113.5(16) . . ?
C31 N31 C33 102.9(13) . . ?
C35 N31 C33 91.5(10) . . ?
N31 C31 C32 117.6(10) . . ?
N31 C31 H31A 107.9 . . ?
C32 C31 H31A 107.9 . . ?
N31 C31 H31B 107.9 . . ?
C32 C31 H31B 107.9 . . ?
H31A C31 H31B 107.2 . . ?
N32 C32 C31 111.4(11) . . ?
N32 C32 H32A 109.4 . . ?
C31 C32 H32A 109.4 . . ?
N32 C32 H32B 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C34 C33 N31 111.3(9) . . ?
C34 C33 H33A 109.4 . . ?
N31 C33 H33A 109.4 . . ?
C34 C33 H33B 109.4 . . ?
N31 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C33 C34 N32 102.9(8) . . ?
C33 C34 H34A 111.2 . . ?
N32 C34 H34A 111.2 . . ?
C33 C34 H34B 111.2 . . ?
N32 C34 H34B 111.2 . . ?
H34A C34 H34B 109.1 . . ?
C36 C35 N31 113.9(10) . . ?
C36 C35 H35A 108.8 . . ?
N31 C35 H35A 108.8 . . ?
C36 C35 H35B 108.8 . . ?
N31 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
N32 C36 C35 105.8(10) . . ?
N32 C36 H36A 110.6 . . ?
C35 C36 H36A 110.6 . . ?
N32 C36 H36B 110.6 . . ?
C35 C36 H36B 110.6 . . ?
H36A C36 H36B 108.7 . . ?
C32 N32 C36 125.1(18) . . ?
C32 N32 C34 113.7(19) . . ?
C36 N32 C34 97.0(11) . . ?
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
F1 C15 1.370(3) . ?
F2 C18 1.364(3) . ?
F3 C25 1.363(3) . ?
F4 C22 1.361(3) . ?
C1 C2 1.368(3) . ?
C1 C10 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.406(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 C14 1.479(3) . ?
C4 C11 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 C12 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 C20 1.478(3) . ?
C7 C8 1.370(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.382(3) . ?
C8 H8 0.9300 . ?
N9 C13 1.368(3) . ?
N9 C10 1.374(3) . ?
N9 H9 0.89(2) . ?
C10 C11 1.406(3) . ?
C11 C12 1.443(3) . ?
C12 C13 1.403(3) . ?
C14 C15 1.383(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.364(3) . ?
C16 C17 1.367(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C20 C25 1.387(3) . ?
C21 C22 1.359(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(3) . ?
C23 C24 1.367(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(3) . ?
C24 H24 0.9300 . ?
N31 C31 1.254(19) . ?
N31 C35 1.55(2) . ?
N31 C33 1.760(16) . ?
C31 C32 1.565(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N32 1.114(16) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.542(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 N32 1.68(2) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.523(10) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 N32 1.47(2) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
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
N9 H9 N31 0.89(2) 2.00(3) 2.86(2) 163(2) . yes
N9 H9 N32 0.89(2) 2.08(3) 2.93(2) 161(2) 3_765 yes
C24 H24 F4 0.93 2.66 3.496(3) 150.5 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
C10 C1 C2 C3 1.3(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C14 -177.2(2) . . . . ?
C2 C3 C4 C11 -2.0(3) . . . . ?
C14 C3 C4 C11 175.5(2) . . . . ?
C12 C5 C6 C7 -0.6(3) . . . . ?
C12 C5 C6 C20 175.4(2) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C20 C6 C7 C8 -174.6(2) . . . . ?
C6 C7 C8 C13 -0.4(4) . . . . ?
C13 N9 C10 C1 -176.1(3) . . . . ?
C13 N9 C10 C11 0.9(3) . . . . ?
C2 C1 C10 N9 175.4(2) . . . . ?
C2 C1 C10 C11 -1.3(4) . . . . ?
C3 C4 C11 C10 2.1(3) . . . . ?
C3 C4 C11 C12 -175.2(2) . . . . ?
N9 C10 C11 C4 -177.7(2) . . . . ?
C1 C10 C11 C4 -0.4(4) . . . . ?
N9 C10 C11 C12 0.2(3) . . . . ?
C1 C10 C11 C12 177.6(2) . . . . ?
C6 C5 C12 C13 -1.1(3) . . . . ?
C6 C5 C12 C11 178.3(2) . . . . ?
C4 C11 C12 C5 -3.2(5) . . . . ?
C10 C11 C12 C5 179.3(2) . . . . ?
C4 C11 C12 C13 176.3(3) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C10 N9 C13 C8 177.5(2) . . . . ?
C10 N9 C13 C12 -1.7(3) . . . . ?
C7 C8 C13 N9 179.6(2) . . . . ?
C7 C8 C13 C12 -1.3(4) . . . . ?
C5 C12 C13 N9 -178.6(2) . . . . ?
C11 C12 C13 N9 1.8(3) . . . . ?
C5 C12 C13 C8 2.1(3) . . . . ?
C11 C12 C13 C8 -177.5(2) . . . . ?
C4 C3 C14 C15 154.5(2) . . . . ?
C2 C3 C14 C15 -28.1(4) . . . . ?
C4 C3 C14 C19 -26.3(3) . . . . ?
C2 C3 C14 C19 151.1(2) . . . . ?
C19 C14 C15 C16 1.7(4) . . . . ?
C3 C14 C15 C16 -179.1(2) . . . . ?
C19 C14 C15 F1 -177.8(2) . . . . ?
C3 C14 C15 F1 1.5(4) . . . . ?
F1 C15 C16 C17 178.4(2) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 F2 -177.9(2) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
F2 C18 C19 C14 178.5(2) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
C3 C14 C19 C18 179.8(2) . . . . ?
C5 C6 C20 C21 -39.3(3) . . . . ?
C7 C6 C20 C21 136.6(2) . . . . ?
C5 C6 C20 C25 142.5(3) . . . . ?
C7 C6 C20 C25 -41.5(4) . . . . ?
C25 C20 C21 C22 0.1(4) . . . . ?
C6 C20 C21 C22 -178.2(2) . . . . ?
C20 C21 C22 F4 -179.4(2) . . . . ?
C20 C21 C22 C23 1.4(4) . . . . ?
C21 C22 C23 C24 -1.7(4) . . . . ?
F4 C22 C23 C24 179.1(2) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C23 C24 C25 F3 -177.8(2) . . . . ?
C23 C24 C25 C20 0.9(4) . . . . ?
C21 C20 C25 C24 -1.2(4) . . . . ?
C6 C20 C25 C24 177.0(2) . . . . ?
C21 C20 C25 F3 177.4(2) . . . . ?
C6 C20 C25 F3 -4.3(4) . . . . ?
C35 N31 C31 C32 -39.4(18) . . . . ?
C33 N31 C31 C32 58.1(16) . . . . ?
N31 C31 C32 N32 -4.0(19) . . . . ?
C31 N31 C33 C34 -50.2(16) . . . . ?
C35 N31 C33 C34 64.3(12) . . . . ?
N31 C33 C34 N32 -1.3(11) . . . . ?
C31 N31 C35 C36 40.4(17) . . . . ?
C33 N31 C35 C36 -64.4(13) . . . . ?
N31 C35 C36 N32 -2.3(15) . . . . ?
C31 C32 N32 C36 54(3) . . . . ?
C31 C32 N32 C34 -64(2) . . . . ?
C35 C36 N32 C32 -50(3) . . . . ?
C35 C36 N32 C34 75.9(11) . . . . ?
C33 C34 N32 C32 62.2(19) . . . . ?
C33 C34 N32 C36 -71.1(11) . . . . ?
