#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:53:59 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267084 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/97/1559776.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_1559776
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 H37 F8 N4'
_chemical_formula_weight         893.87
_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     'Dual space'
_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                 95.7210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6570(3)
_cell_length_b                   14.8520(6)
_cell_length_c                   21.2537(8)
_cell_measurement_reflns_used    9418
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.9545
_cell_measurement_theta_min      2.9812
_cell_volume                     2090.88(15)
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_collection       'Bruker APEX 3'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            73120
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         32.966
_diffrn_reflns_theta_min         1.975
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       block
_exptl_crystal_F_000             922
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         7264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0474
_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)+(0.0720P)²+0.4843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6595
_reflns_number_total             7264
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05899h2.cif
_cod_data_source_block           ANH-BRM-2-100K
_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               1559776
_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   0.962
_shelx_estimated_absorpt_t_max   0.989
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 -0.02982(8) 0.23566(4) 0.15420(3) 0.02471(13) Uani 1 1 d . . . . .
F2 F 0.04044(10) 0.15279(4) 0.40387(3) 0.02865(14) Uani 1 1 d . . . . .
F3 F 1.40512(8) 0.53934(4) 0.42479(3) 0.02702(13) Uani 1 1 d . . . . .
F4 F 0.77975(9) 0.68865(5) 0.53287(3) 0.03119(15) Uani 1 1 d . . . . .
C1 C 0.54392(14) 0.32946(6) 0.14329(4) 0.02025(16) Uani 1 1 d . . . . .
H1 H 0.570376 0.323120 0.100412 0.024 Uiso 1 1 calc R U . . .
C2 C 0.37970(13) 0.28705(6) 0.16578(4) 0.01928(15) Uani 1 1 d . . . . .
H2 H 0.294167 0.250809 0.137693 0.023 Uiso 1 1 calc R U . . .
C3 C 0.33558(12) 0.29611(5) 0.22931(4) 0.01643(14) Uani 1 1 d . . . . .
C4 C 0.45976(12) 0.35081(5) 0.27028(4) 0.01568(14) Uani 1 1 d . . . . .
H4 H 0.429735 0.359387 0.312636 0.019 Uiso 1 1 calc R U . . .
C5 C 0.83518(12) 0.48084(5) 0.33992(4) 0.01539(14) Uani 1 1 d . . . . .
H5 H 0.744838 0.471272 0.371166 0.018 Uiso 1 1 calc R U . . .
C6 C 1.01344(12) 0.52963(5) 0.35458(4) 0.01580(14) Uani 1 1 d . . . . .
C7 C 1.14624(12) 0.54318(5) 0.30750(4) 0.01760(15) Uani 1 1 d . . . . .
H7 H 1.268649 0.575060 0.318132 0.021 Uiso 1 1 calc R U . . .
C8 C 1.10335(12) 0.51139(6) 0.24635(4) 0.01828(15) Uani 1 1 d . . . . .
H8 H 1.192660 0.522067 0.214970 0.022 Uiso 1 1 calc R U . . .
N9 N 0.84691(11) 0.42514(5) 0.17605(3) 0.01886(14) Uani 1 1 d . . . . .
H9 H 0.899(2) 0.4312(9) 0.1382(6) 0.023 Uiso 1 1 d . U . . .
C10 C 0.66906(12) 0.38161(5) 0.18528(4) 0.01726(15) Uani 1 1 d . . . . .
C11 C 0.62770(12) 0.39273(5) 0.24886(4) 0.01537(14) Uani 1 1 d . . . . .
C12 C 0.79113(12) 0.44635(5) 0.27908(4) 0.01499(14) Uani 1 1 d . . . . .
C13 C 0.92433(12) 0.46312(5) 0.23239(4) 0.01639(14) Uani 1 1 d . . . . .
C14 C 0.16689(12) 0.24657(5) 0.25408(4) 0.01675(14) Uani 1 1 d . . . . .
C15 C -0.00911(13) 0.21911(6) 0.21737(4) 0.01930(15) Uani 1 1 d . . . . .
C16 C -0.16774(13) 0.17475(6) 0.24148(5) 0.02339(17) Uani 1 1 d . . . . .
H16 H -0.285355 0.159497 0.214553 0.028 Uiso 1 1 calc R U . . .
C17 C -0.15364(14) 0.15280(6) 0.30510(5) 0.02427(18) Uani 1 1 d . . . . .
H17 H -0.260152 0.122370 0.322843 0.029 Uiso 1 1 calc R U . . .
C18 C 0.02081(14) 0.17680(6) 0.34172(4) 0.02107(16) Uani 1 1 d . . . . .
C19 C 0.17794(12) 0.22267(6) 0.31836(4) 0.01862(15) Uani 1 1 d . . . . .
H19 H 0.294107 0.238151 0.345869 0.022 Uiso 1 1 calc R U . . .
C20 C 1.05447(12) 0.57229(5) 0.41753(4) 0.01602(14) Uani 1 1 d . . . . .
C21 C 0.89698(12) 0.61087(6) 0.44746(4) 0.01862(15) Uani 1 1 d . . . . .
H21 H 0.762357 0.608012 0.427966 0.022 Uiso 1 1 calc R U . . .
C22 C 0.93731(13) 0.65299(6) 0.50520(4) 0.02078(16) Uani 1 1 d . . . . .
C23 C 1.12985(14) 0.66126(6) 0.53582(4) 0.02209(16) Uani 1 1 d . . . . .
H23 H 1.153213 0.692090 0.575032 0.027 Uiso 1 1 calc R U . . .
C24 C 1.28782(13) 0.62282(6) 0.50710(4) 0.02229(17) Uani 1 1 d . . . . .
H24 H 1.422317 0.626630 0.526592 0.027 Uiso 1 1 calc R U . . .
C25 C 1.24711(12) 0.57901(6) 0.44993(4) 0.01880(15) Uani 1 1 d . . . . .
N31 N 0.9752(19) 0.4599(8) 0.0503(5) 0.0230(10) Uani 0.5 1 d . . P A -1
C31 C 0.8331(3) 0.43472(15) 0.00116(9) 0.0296(4) Uani 0.5 1 d . . P A -1
H31A H 0.697734 0.454434 0.011104 0.035 Uiso 0.5 1 calc R U P A -1
H31B H 0.831254 0.368240 -0.002242 0.035 Uiso 0.5 1 calc R U P A -1
C32 C 0.8763(3) 0.47549(14) -0.06345(8) 0.0266(4) Uani 0.5 1 d . . P A -1
H32A H 0.902523 0.426349 -0.093024 0.032 Uiso 0.5 1 calc R U P A -1
H32B H 0.756459 0.509358 -0.081829 0.032 Uiso 0.5 1 calc R U P A -1
C33 C 0.9365(3) 0.57199(14) 0.05361(9) 0.0272(4) Uani 0.5 1 d . . P A -1
H33A H 0.798007 0.584095 0.064603 0.033 Uiso 0.5 1 calc R U P A -1
H33B H 1.033149 0.598996 0.086743 0.033 Uiso 0.5 1 calc R U P A -1
C34 C 0.9657(3) 0.61464(13) -0.01148(9) 0.0275(4) Uani 0.5 1 d . . P A -1
H34A H 1.070305 0.662211 -0.006789 0.033 Uiso 0.5 1 calc R U P A -1
H34B H 0.837806 0.641559 -0.030547 0.033 Uiso 0.5 1 calc R U P A -1
C35 C 1.1801(3) 0.45773(15) 0.03862(9) 0.0281(4) Uani 0.5 1 d . . P A -1
H35A H 1.224552 0.394229 0.037086 0.034 Uiso 0.5 1 calc R U P A -1
H35B H 1.262100 0.487386 0.074153 0.034 Uiso 0.5 1 calc R U P A -1
C36 C 1.2202(3) 0.50492(16) -0.02400(9) 0.0286(4) Uani 0.5 1 d . . P A -1
H36 H 1.349483 0.514495 -0.038108 0.034 Uiso 0.5 1 calc R U P A -1
N32 N 1.037(2) 0.5311(9) -0.0563(5) 0.0303(19) 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 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 '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 118.24(7) . . ?
C2 C1 H1 120.9 . . ?
C10 C1 H1 120.9 . . ?
C1 C2 C3 122.05(7) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 118.85(7) . . ?
C4 C3 C14 119.25(7) . . ?
C2 C3 C14 121.86(7) . . ?
C11 C4 C3 119.93(7) . . ?
C11 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C12 C5 C6 119.48(7) . . ?
C12 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 119.50(7) . . ?
C5 C6 C20 119.93(7) . . ?
C7 C6 C20 120.42(7) . . ?
C8 C7 C6 122.03(7) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 117.76(7) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
C13 N9 C10 108.69(7) . . ?
C13 N9 H9 125.9(9) . . ?
C10 N9 H9 125.2(9) . . ?
N9 C10 C1 129.49(7) . . ?
N9 C10 C11 109.41(7) . . ?
C1 C10 C11 121.03(8) . . ?
C4 C11 C10 119.86(7) . . ?
C4 C11 C12 133.84(7) . . ?
C10 C11 C12 106.20(7) . . ?
C5 C12 C13 119.75(7) . . ?
C5 C12 C11 133.91(7) . . ?
C13 C12 C11 106.34(7) . . ?
N9 C13 C8 129.24(7) . . ?
N9 C13 C12 109.33(7) . . ?
C8 C13 C12 121.43(7) . . ?
C15 C14 C19 115.28(8) . . ?
C15 C14 C3 124.57(8) . . ?
C19 C14 C3 120.14(7) . . ?
F1 C15 C16 116.46(7) . . ?
F1 C15 C14 119.62(8) . . ?
C16 C15 C14 123.92(8) . . ?
C17 C16 C15 119.54(8) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 117.49(8) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
F2 C18 C17 118.28(8) . . ?
F2 C18 C19 118.35(8) . . ?
C17 C18 C19 123.36(9) . . ?
C18 C19 C14 120.36(8) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C25 C20 C21 116.00(7) . . ?
C25 C20 C6 123.60(7) . . ?
C21 C20 C6 120.39(7) . . ?
C22 C21 C20 120.06(7) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
F4 C22 C21 118.10(7) . . ?
F4 C22 C23 118.70(8) . . ?
C21 C22 C23 123.19(8) . . ?
C22 C23 C24 117.57(8) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C25 C24 C23 119.28(8) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
F3 C25 C24 117.26(7) . . ?
F3 C25 C20 118.87(7) . . ?
C24 C25 C20 123.86(8) . . ?
C31 N31 C35 117.4(9) . . ?
C31 N31 C33 101.7(6) . . ?
C35 N31 C33 100.6(7) . . ?
N31 C31 C32 112.8(4) . . ?
N31 C31 H31A 109.0 . . ?
C32 C31 H31A 109.0 . . ?
N31 C31 H31B 109.0 . . ?
C32 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
N32 C32 C31 110.8(5) . . ?
N32 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N32 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 N31 109.4(4) . . ?
C34 C33 H33A 109.8 . . ?
N31 C33 H33A 109.8 . . ?
C34 C33 H33B 109.8 . . ?
N31 C33 H33B 109.8 . . ?
H33A C33 H33B 108.2 . . ?
C33 C34 N32 106.0(4) . . ?
C33 C34 H34A 110.5 . . ?
N32 C34 H34A 110.5 . . ?
C33 C34 H34B 110.5 . . ?
N32 C34 H34B 110.5 . . ?
H34A C34 H34B 108.7 . . ?
N31 C35 C36 113.1(4) . . ?
N31 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
N31 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
N32 C36 C35 109.5(5) . . ?
N32 C36 H36 125.3 . . ?
C35 C36 H36 125.3 . . ?
C32 N32 C36 122.0(9) . . ?
C32 N32 C34 104.5(8) . . ?
C36 N32 C34 102.2(8) . . ?
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 1.3583(10) . ?
F2 C18 1.3618(11) . ?
F3 C25 1.3606(10) . ?
F4 C22 1.3598(10) . ?
C1 C2 1.3872(12) . ?
C1 C10 1.3935(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.4167(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.3993(11) . ?
C3 C14 1.4823(11) . ?
C4 C11 1.3951(11) . ?
C4 H4 0.9500 . ?
C5 C12 1.3946(11) . ?
C5 C6 1.3988(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.4141(11) . ?
C6 C20 1.4809(11) . ?
C7 C8 1.3855(12) . ?
C7 H7 0.9500 . ?
C8 C13 1.3971(11) . ?
C8 H8 0.9500 . ?
N9 C13 1.3764(10) . ?
N9 C10 1.3800(11) . ?
N9 H9 0.911(13) . ?
C10 C11 1.4154(11) . ?
C11 C12 1.4460(11) . ?
C12 C13 1.4172(11) . ?
C14 C15 1.4020(11) . ?
C14 C19 1.4064(12) . ?
C15 C16 1.3854(12) . ?
C16 C17 1.3851(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.3789(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.3815(11) . ?
C19 H19 0.9500 . ?
C20 C25 1.3974(11) . ?
C20 C21 1.4018(11) . ?
C21 C22 1.3799(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.3839(12) . ?
C23 C24 1.3901(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.3811(12) . ?
C24 H24 0.9500 . ?
N31 C31 1.389(12) . ?
N31 C35 1.411(13) . ?
N31 C33 1.687(12) . ?
C31 C32 1.554(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.350(13) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.551(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.664(14) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.551(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.392(12) . ?
C36 H36 0.9500 . ?
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 0.911(13) 2.029(17) 2.932(11) 170.2(13) . yes
N9 H9 N32 0.911(13) 1.915(17) 2.807(11) 165.7(13) 3_765 yes
C24 H24 F4 0.95 2.54 3.4092(10) 151.7 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 0.66(13) . . . . ?
C1 C2 C3 C4 1.12(12) . . . . ?
C1 C2 C3 C14 -176.46(8) . . . . ?
C2 C3 C4 C11 -2.23(11) . . . . ?
C14 C3 C4 C11 175.41(7) . . . . ?
C12 C5 C6 C7 -0.04(11) . . . . ?
C12 C5 C6 C20 175.47(7) . . . . ?
C5 C6 C7 C8 1.60(12) . . . . ?
C20 C6 C7 C8 -173.88(7) . . . . ?
C6 C7 C8 C13 -1.31(12) . . . . ?
C13 N9 C10 C1 -175.85(9) . . . . ?
C13 N9 C10 C11 1.00(9) . . . . ?
C2 C1 C10 N9 175.20(8) . . . . ?
C2 C1 C10 C11 -1.33(12) . . . . ?
C3 C4 C11 C10 1.59(11) . . . . ?
C3 C4 C11 C12 -174.49(8) . . . . ?
N9 C10 C11 C4 -176.93(7) . . . . ?
C1 C10 C11 C4 0.23(12) . . . . ?
N9 C10 C11 C12 0.12(9) . . . . ?
C1 C10 C11 C12 177.28(8) . . . . ?
C6 C5 C12 C13 -1.71(11) . . . . ?
C6 C5 C12 C11 178.41(8) . . . . ?
C4 C11 C12 C5 -4.80(16) . . . . ?
C10 C11 C12 C5 178.75(8) . . . . ?
C4 C11 C12 C13 175.31(8) . . . . ?
C10 C11 C12 C13 -1.15(8) . . . . ?
C10 N9 C13 C8 178.10(8) . . . . ?
C10 N9 C13 C12 -1.75(9) . . . . ?
C7 C8 C13 N9 179.67(8) . . . . ?
C7 C8 C13 C12 -0.49(12) . . . . ?
C5 C12 C13 N9 -178.12(7) . . . . ?
C11 C12 C13 N9 1.79(9) . . . . ?
C5 C12 C13 C8 2.01(12) . . . . ?
C11 C12 C13 C8 -178.08(7) . . . . ?
C4 C3 C14 C15 154.24(8) . . . . ?
C2 C3 C14 C15 -28.20(12) . . . . ?
C4 C3 C14 C19 -26.76(11) . . . . ?
C2 C3 C14 C19 150.81(8) . . . . ?
C19 C14 C15 F1 -177.17(7) . . . . ?
C3 C14 C15 F1 1.88(12) . . . . ?
C19 C14 C15 C16 2.58(12) . . . . ?
C3 C14 C15 C16 -178.37(8) . . . . ?
F1 C15 C16 C17 177.68(8) . . . . ?
C14 C15 C16 C17 -2.08(13) . . . . ?
C15 C16 C17 C18 0.04(13) . . . . ?
C16 C17 C18 F2 -177.59(8) . . . . ?
C16 C17 C18 C19 1.35(14) . . . . ?
F2 C18 C19 C14 178.17(8) . . . . ?
C17 C18 C19 C14 -0.77(13) . . . . ?
C15 C14 C19 C18 -1.15(12) . . . . ?
C3 C14 C19 C18 179.76(7) . . . . ?
C5 C6 C20 C25 144.43(8) . . . . ?
C7 C6 C20 C25 -40.11(11) . . . . ?
C5 C6 C20 C21 -37.16(11) . . . . ?
C7 C6 C20 C21 138.30(8) . . . . ?
C25 C20 C21 C22 0.56(12) . . . . ?
C6 C20 C21 C22 -177.97(8) . . . . ?
C20 C21 C22 F4 -179.31(8) . . . . ?
C20 C21 C22 C23 1.28(14) . . . . ?
F4 C22 C23 C24 178.86(8) . . . . ?
C21 C22 C23 C24 -1.73(14) . . . . ?
C22 C23 C24 C25 0.33(13) . . . . ?
C23 C24 C25 F3 -177.46(8) . . . . ?
C23 C24 C25 C20 1.56(13) . . . . ?
C21 C20 C25 F3 177.03(7) . . . . ?
C6 C20 C25 F3 -4.50(12) . . . . ?
C21 C20 C25 C24 -1.98(12) . . . . ?
C6 C20 C25 C24 176.49(8) . . . . ?
C35 N31 C31 C32 -43.7(9) . . . . ?
C33 N31 C31 C32 64.9(7) . . . . ?
N31 C31 C32 N32 -3.7(3) . . . . ?
C31 N31 C33 C34 -57.9(7) . . . . ?
C35 N31 C33 C34 63.2(6) . . . . ?
N31 C33 C34 N32 -3.4(2) . . . . ?
C31 N31 C35 C36 48.5(9) . . . . ?
C33 N31 C35 C36 -60.7(7) . . . . ?
N31 C35 C36 N32 -5.3(3) . . . . ?
C31 C32 N32 C36 50.6(12) . . . . ?
C31 C32 N32 C34 -64.2(6) . . . . ?
C35 C36 N32 C32 -45.6(12) . . . . ?
C35 C36 N32 C34 70.4(6) . . . . ?
C33 C34 N32 C32 65.4(6) . . . . ?
C33 C34 N32 C36 -62.7(7) . . . . ?
