#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:53:59 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267084 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/97/1559769.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_1559769
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_absolute_configuration rm
_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           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 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                 106.4326(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9524(6)
_cell_length_b                   14.0942(5)
_cell_length_c                   22.7794(8)
_cell_measurement_reflns_used    9628
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      29.9371
_cell_measurement_theta_min      2.5276
_cell_volume                     4296.5(3)
_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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_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_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5794
_diffrn_reflns_point_group_measured_fraction_full 0.498
_diffrn_reflns_point_group_measured_fraction_max 0.498
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_min         2.152
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.876
_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    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             1848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         5794
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0372
_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)+(0.0637P)²+0.1055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                4894
_reflns_number_total             5794
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05899h2.cif
_cod_data_source_block           ANH-BRM-1HT-300K
_cod_depositor_comments
;Adding full bibliography for 1559768--1559785.cif.

 Adding full bibliography for 1559768--1559785.cif.
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1559769
_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   0.989
_shelx_estimated_absorpt_t_max   0.997
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'
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 0.5369(3) -0.16416(17) 0.64658(13) 0.1058(9) Uani 1 1 d . . . . .
F2 F 0.7117(2) -0.09221(17) 0.84831(11) 0.1036(9) Uani 1 1 d . . . . .
F3 F 0.6830(4) 0.7542(2) 1.01370(14) 0.1339(14) Uani 1 1 d . . . . .
F4 F 0.8614(3) 0.4697(3) 1.05828(11) 0.1355(14) Uani 1 1 d . . . . .
C1 C 0.5724(3) 0.2887(2) 0.62540(10) 0.0592(7) Uani 1 1 d . . . . .
H1 H 0.555263 0.306183 0.584380 0.071 Uiso 1 1 calc R U . . .
C2 C 0.5816(3) 0.1946(2) 0.64210(11) 0.0587(7) Uani 1 1 d . . . . .
H2 H 0.572101 0.148615 0.611696 0.070 Uiso 1 1 calc R U . . .
C3 C 0.6049(2) 0.16551(18) 0.70368(10) 0.0476(5) Uani 1 1 d . . . . .
C4 C 0.62201(19) 0.23473(17) 0.74918(9) 0.0447(4) Uani 1 1 d . . . . .
H4 H 0.638062 0.216944 0.790133 0.054 Uiso 1 1 calc R U . . .
C5 C 0.6605(2) 0.43920(19) 0.83060(10) 0.0484(5) Uani 1 1 d . . . . .
H5 H 0.673095 0.391005 0.859673 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6714(2) 0.53374(19) 0.84888(10) 0.0516(5) Uani 1 1 d . . . . .
C7 C 0.6505(3) 0.6055(2) 0.80408(13) 0.0607(7) Uani 1 1 d . . . . .
H7 H 0.657277 0.668520 0.816630 0.073 Uiso 1 1 calc R U . . .
C8 C 0.6205(3) 0.5859(2) 0.74278(12) 0.0613(7) Uani 1 1 d . . . . .
H8 H 0.606738 0.634572 0.714017 0.074 Uiso 1 1 calc R U . . .
N9 N 0.5859(2) 0.45466(18) 0.66675(9) 0.0569(6) Uani 1 1 d . . . . .
H9 H 0.556(3) 0.480(3) 0.6327(19) 0.068 Uiso 1 1 d . U . . .
C10 C 0.5893(2) 0.35679(19) 0.67106(10) 0.0507(5) Uani 1 1 d . . . . .
C11 C 0.61512(19) 0.33019(17) 0.73347(9) 0.0438(4) Uani 1 1 d . . . . .
C12 C 0.6305(2) 0.41715(18) 0.76810(9) 0.0446(5) Uani 1 1 d . . . . .
C13 C 0.6112(2) 0.49225(19) 0.72478(10) 0.0502(5) Uani 1 1 d . . . . .
C14 C 0.6113(2) 0.06245(19) 0.71913(11) 0.0483(5) Uani 1 1 d . . . . .
C15 C 0.5700(3) -0.0056(2) 0.67483(13) 0.0596(6) Uani 1 1 d . . . . .
H15 H 0.536989 0.012505 0.634980 0.072 Uiso 1 1 calc R U . . .
C16 C 0.5789(3) -0.0996(3) 0.69088(16) 0.0702(8) Uani 1 1 d . . . . .
C17 C 0.6250(3) -0.1323(2) 0.74836(18) 0.0725(8) Uani 1 1 d . . . . .
H17 H 0.629266 -0.196525 0.758109 0.087 Uiso 1 1 calc R U . . .
C18 C 0.6642(3) -0.0636(2) 0.79036(15) 0.0676(8) Uani 1 1 d . . . . .
C19 C 0.6609(2) 0.0317(2) 0.77831(12) 0.0561(6) Uani 1 1 d . . . . .
H19 H 0.690818 0.074983 0.808792 0.067 Uiso 1 1 calc R U . . .
C20 C 0.7061(3) 0.5607(2) 0.91458(12) 0.0591(7) Uani 1 1 d . . . . .
C21 C 0.6771(3) 0.6463(2) 0.93472(14) 0.0715(9) Uani 1 1 d . . . . .
H21 H 0.634475 0.687055 0.907217 0.086 Uiso 1 1 calc R U . . .
C22 C 0.7123(4) 0.6706(3) 0.99605(17) 0.0955(16) Uani 1 1 d . . . . .
C23 C 0.7747(5) 0.6139(4) 1.03870(15) 0.1000(17) Uani 1 1 d . . . . .
H23 H 0.798168 0.631414 1.079624 0.120 Uiso 1 1 calc R U . . .
C24 C 0.8005(4) 0.5298(4) 1.01763(15) 0.0896(14) Uani 1 1 d . . . . .
C25 C 0.7698(3) 0.5004(3) 0.95692(12) 0.0711(9) Uani 1 1 d . . . . .
H25 H 0.790779 0.442863 0.944894 0.085 Uiso 1 1 calc R U . . .
N31 N 0.5194(2) 0.56536(16) 0.55618(9) 0.0572(5) Uani 1 1 d . . . . .
C31 C 0.5994(3) 0.6270(3) 0.55156(14) 0.0682(7) Uani 1 1 d . . . . .
H31A H 0.659752 0.590111 0.556230 0.082 Uiso 1 1 calc R U . . .
H31B H 0.612441 0.673701 0.584166 0.082 Uiso 1 1 calc R U . . .
C32 C 0.5717(3) 0.6778(3) 0.48930(15) 0.0736(8) Uani 1 1 d . . . . .
H32A H 0.575566 0.745937 0.495585 0.088 Uiso 1 1 calc R U . . .
H32B H 0.618815 0.660347 0.466944 0.088 Uiso 1 1 calc R U . . .
C33 C 0.4301(3) 0.6241(3) 0.55013(15) 0.0765(8) Uani 1 1 d . . . . .
H33A H 0.443194 0.670580 0.582869 0.092 Uiso 1 1 calc R U . . .
H33B H 0.374933 0.584496 0.553299 0.092 Uiso 1 1 calc R U . . .
C34 C 0.4020(3) 0.6752(3) 0.48768(17) 0.0762(9) Uani 1 1 d . . . . .
H34A H 0.335170 0.656668 0.464332 0.091 Uiso 1 1 calc R U . . .
H34B H 0.402278 0.743244 0.494063 0.091 Uiso 1 1 calc R U . . .
C35 C 0.4981(3) 0.49707(19) 0.50540(13) 0.0680(7) Uani 1 1 d . . . . .
H35A H 0.444716 0.454908 0.508416 0.082 Uiso 1 1 calc R U . . .
H35B H 0.557028 0.458953 0.508063 0.082 Uiso 1 1 calc R U . . .
C36 C 0.4671(3) 0.54891(19) 0.44359(11) 0.0623(7) Uani 1 1 d . . . . .
H36A H 0.511834 0.531538 0.419583 0.075 Uiso 1 1 calc R U . . .
H36B H 0.399852 0.530456 0.420972 0.075 Uiso 1 1 calc R U . . .
N32 N 0.4712(2) 0.65181(15) 0.45396(9) 0.0562(5) Uani 1 1 d . . . . .
F41 F 0.1410(3) 0.4675(2) -0.00898(13) 0.1214(12) Uani 1 1 d . . . . .
F42 F 0.2893(3) 0.7419(2) -0.05847(10) 0.1099(9) Uani 1 1 d . . . . .
F43 F 0.4103(4) 1.36585(17) 0.36502(14) 0.1380(16) Uani 1 1 d . . . . .
F44 F 0.3368(3) 1.29594(17) 0.15802(11) 0.1064(9) Uani 1 1 d . . . . .
C41 C 0.3850(2) 0.61565(18) 0.26036(11) 0.0538(6) Uani 1 1 d . . . . .
H41 H 0.402256 0.566257 0.288446 0.065 Uiso 1 1 calc R U . . .
C42 C 0.3497(2) 0.59824(18) 0.19832(11) 0.0541(6) Uani 1 1 d . . . . .
H42 H 0.343092 0.535754 0.184637 0.065 Uiso 1 1 calc R U . . .
C43 C 0.3236(2) 0.67193(17) 0.15520(10) 0.0487(5) Uani 1 1 d . . . . .
C44 C 0.3335(2) 0.76626(18) 0.17471(10) 0.0473(5) Uani 1 1 d . . . . .
H44 H 0.317032 0.815518 0.146473 0.057 Uiso 1 1 calc R U . . .
C45 C 0.3776(2) 0.96826(17) 0.25779(10) 0.0461(5) Uani 1 1 d . . . . .
H45 H 0.351733 0.986901 0.217210 0.055 Uiso 1 1 calc R U . . .
C46 C 0.4047(2) 1.03630(18) 0.30348(11) 0.0485(5) Uani 1 1 d . . . . .
C47 C 0.4442(2) 1.0054(2) 0.36452(11) 0.0612(7) Uani 1 1 d . . . . .
H47 H 0.464762 1.050590 0.395250 0.073 Uiso 1 1 calc R U . . .
C48 C 0.4535(3) 0.9111(2) 0.38025(11) 0.0646(8) Uani 1 1 d . . . . .
H48 H 0.477961 0.892666 0.420961 0.078 Uiso 1 1 calc R U . . .
N49 N 0.4287(2) 0.74611(18) 0.33751(9) 0.0576(6) Uani 1 1 d . . . . .
H49 H 0.447(3) 0.705(3) 0.3723(18) 0.069 Uiso 1 1 d . U . . .
C50 C 0.3936(2) 0.71027(19) 0.27932(10) 0.0477(5) Uani 1 1 d . . . . .
C51 C 0.3682(2) 0.78537(17) 0.23703(10) 0.0446(5) Uani 1 1 d . . . . .
C52 C 0.3889(2) 0.87230(18) 0.27232(9) 0.0453(4) Uani 1 1 d . . . . .
C53 C 0.4255(2) 0.84384(19) 0.33402(10) 0.0503(6) Uani 1 1 d . . . . .
C54 C 0.2861(2) 0.6483(2) 0.08889(11) 0.0534(5) Uani 1 1 d . . . . .
C55 C 0.2289(3) 0.5670(2) 0.06990(14) 0.0678(7) Uani 1 1 d . . . . .
H55 H 0.213565 0.527132 0.098508 0.081 Uiso 1 1 calc R U . . .
C56 C 0.1954(4) 0.5461(3) 0.00845(16) 0.0815(11) Uani 1 1 d . . . . .
C57 C 0.2143(4) 0.6019(3) -0.03624(14) 0.0851(12) Uani 1 1 d . . . . .
H57 H 0.190961 0.586645 -0.077561 0.102 Uiso 1 1 calc R U . . .
C58 C 0.2702(3) 0.6821(3) -0.01591(14) 0.0737(9) Uani 1 1 d . . . . .
C59 C 0.3067(3) 0.7071(2) 0.04478(12) 0.0601(7) Uani 1 1 d . . . . .
H59 H 0.344247 0.762028 0.056104 0.072 Uiso 1 1 calc R U . . .
C60 C 0.3940(2) 1.13933(18) 0.28912(11) 0.0477(5) Uani 1 1 d . . . . .
C61 C 0.4081(3) 1.2071(2) 0.33515(14) 0.0669(8) Uani 1 1 d . . . . .
H61 H 0.424618 1.188694 0.375991 0.080 Uiso 1 1 calc R U . . .
C62 C 0.3972(3) 1.3021(2) 0.31967(17) 0.0745(9) Uani 1 1 d . . . . .
C63 C 0.3747(3) 1.3345(2) 0.26102(18) 0.0682(8) Uani 1 1 d . . . . .
H63 H 0.369672 1.398901 0.251839 0.082 Uiso 1 1 calc R U . . .
C64 C 0.3601(3) 1.2677(2) 0.21714(15) 0.0652(7) Uani 1 1 d . . . . .
C65 C 0.3695(3) 1.1719(2) 0.22918(13) 0.0617(7) Uani 1 1 d . . . . .
H65 H 0.359418 1.128884 0.197058 0.074 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 0.0034 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 118.5(2) . . ?
C2 C1 H1 120.7 . . ?
C10 C1 H1 120.7 . . ?
C1 C2 C3 122.2(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 C14 121.3(2) . . ?
C2 C3 C14 120.0(2) . . ?
C11 C4 C3 120.11(19) . . ?
C11 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C12 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C12 C5 H5 120.2 . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 C20 121.5(2) . . ?
C7 C6 C20 119.2(2) . . ?
C8 C7 C6 122.4(3) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C13 118.2(2) . . ?
C7 C8 H8 120.9 . . ?
C13 C8 H8 120.9 . . ?
C13 N9 C10 108.79(19) . . ?
C13 N9 H9 130(3) . . ?
C10 N9 H9 119(3) . . ?
N9 C10 C1 130.0(2) . . ?
N9 C10 C11 109.2(2) . . ?
C1 C10 C11 120.8(2) . . ?
C4 C11 C10 119.7(2) . . ?
C4 C11 C12 134.00(19) . . ?
C10 C11 C12 106.3(2) . . ?
C5 C12 C13 119.0(2) . . ?
C5 C12 C11 134.5(2) . . ?
C13 C12 C11 106.50(19) . . ?
N9 C13 C8 129.2(2) . . ?
N9 C13 C12 109.1(2) . . ?
C8 C13 C12 121.6(2) . . ?
C15 C14 C19 118.4(3) . . ?
C15 C14 C3 121.0(2) . . ?
C19 C14 C3 120.6(2) . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
F1 C16 C17 118.2(3) . . ?
F1 C16 C15 117.4(3) . . ?
C17 C16 C15 124.3(3) . . ?
C18 C17 C16 114.9(3) . . ?
C18 C17 H17 122.6 . . ?
C16 C17 H17 122.6 . . ?
F2 C18 C17 117.4(3) . . ?
F2 C18 C19 117.7(3) . . ?
C17 C18 C19 124.9(3) . . ?
C18 C19 C14 118.5(3) . . ?
C18 C19 H19 120.8 . . ?
C14 C19 H19 120.8 . . ?
C21 C20 C25 119.1(3) . . ?
C21 C20 C6 120.8(3) . . ?
C25 C20 C6 120.1(3) . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
F3 C22 C23 119.1(3) . . ?
F3 C22 C21 117.8(5) . . ?
C23 C22 C21 123.1(4) . . ?
C22 C23 C24 115.9(3) . . ?
C22 C23 H23 122.0 . . ?
C24 C23 H23 122.0 . . ?
F4 C24 C23 118.5(3) . . ?
F4 C24 C25 116.7(5) . . ?
C23 C24 C25 124.8(4) . . ?
C24 C25 C20 117.6(4) . . ?
C24 C25 H25 121.2 . . ?
C20 C25 H25 121.2 . . ?
C31 N31 C35 109.0(3) . . ?
C31 N31 C33 107.8(2) . . ?
C35 N31 C33 108.5(3) . . ?
N31 C31 C32 110.5(2) . . ?
N31 C31 H31A 109.5 . . ?
C32 C31 H31A 109.5 . . ?
N31 C31 H31B 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
N32 C32 C31 110.2(3) . . ?
N32 C32 H32A 109.6 . . ?
C31 C32 H32A 109.6 . . ?
N32 C32 H32B 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N31 C33 C34 109.7(3) . . ?
N31 C33 H33A 109.7 . . ?
C34 C33 H33A 109.7 . . ?
N31 C33 H33B 109.7 . . ?
C34 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
N32 C34 C33 110.7(3) . . ?
N32 C34 H34A 109.5 . . ?
C33 C34 H34A 109.5 . . ?
N32 C34 H34B 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
N31 C35 C36 110.6(2) . . ?
N31 C35 H35A 109.5 . . ?
C36 C35 H35A 109.5 . . ?
N31 C35 H35B 109.5 . . ?
C36 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
N32 C36 C35 109.5(2) . . ?
N32 C36 H36A 109.8 . . ?
C35 C36 H36A 109.8 . . ?
N32 C36 H36B 109.8 . . ?
C35 C36 H36B 109.8 . . ?
H36A C36 H36B 108.2 . . ?
C34 N32 C32 109.6(2) . . ?
C34 N32 C36 108.2(3) . . ?
C32 N32 C36 109.0(3) . . ?
C42 C41 C50 117.5(2) . . ?
C42 C41 H41 121.3 . . ?
C50 C41 H41 121.3 . . ?
C41 C42 C43 122.1(2) . . ?
C41 C42 H42 119.0 . . ?
C43 C42 H42 119.0 . . ?
C44 C43 C42 119.9(2) . . ?
C44 C43 C54 120.7(2) . . ?
C42 C43 C54 119.4(2) . . ?
C51 C44 C43 118.9(2) . . ?
C51 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C46 C45 C52 120.4(2) . . ?
C46 C45 H45 119.8 . . ?
C52 C45 H45 119.8 . . ?
C45 C46 C47 118.2(2) . . ?
C45 C46 C60 121.4(2) . . ?
C47 C46 C60 120.3(2) . . ?
C48 C47 C46 122.5(2) . . ?
C48 C47 H47 118.7 . . ?
C46 C47 H47 118.7 . . ?
C47 C48 C53 118.5(2) . . ?
C47 C48 H48 120.7 . . ?
C53 C48 H48 120.7 . . ?
C50 N49 C53 108.35(19) . . ?
C50 N49 H49 121(2) . . ?
C53 N49 H49 130(2) . . ?
N49 C50 C41 128.8(2) . . ?
N49 C50 C51 109.6(2) . . ?
C41 C50 C51 121.6(2) . . ?
C44 C51 C50 120.0(2) . . ?
C44 C51 C52 133.4(2) . . ?
C50 C51 C52 106.51(19) . . ?
C45 C52 C53 119.9(2) . . ?
C45 C52 C51 134.3(2) . . ?
C53 C52 C51 105.7(2) . . ?
N49 C53 C48 129.8(2) . . ?
N49 C53 C52 109.8(2) . . ?
C48 C53 C52 120.4(2) . . ?
C59 C54 C55 118.8(3) . . ?
C59 C54 C43 120.9(3) . . ?
C55 C54 C43 120.3(3) . . ?
C56 C55 C54 119.4(3) . . ?
C56 C55 H55 120.3 . . ?
C54 C55 H55 120.3 . . ?
F41 C56 C57 117.9(3) . . ?
F41 C56 C55 118.7(4) . . ?
C57 C56 C55 123.5(4) . . ?
C56 C57 C58 115.6(3) . . ?
C56 C57 H57 122.2 . . ?
C58 C57 H57 122.2 . . ?
F42 C58 C59 117.7(4) . . ?
F42 C58 C57 118.2(3) . . ?
C59 C58 C57 124.1(4) . . ?
C58 C59 C54 118.6(3) . . ?
C58 C59 H59 120.7 . . ?
C54 C59 H59 120.7 . . ?
C65 C60 C61 117.2(2) . . ?
C65 C60 C46 121.4(2) . . ?
C61 C60 C46 121.4(2) . . ?
C62 C61 C60 119.4(3) . . ?
C62 C61 H61 120.3 . . ?
C60 C61 H61 120.3 . . ?
F43 C62 C63 118.3(3) . . ?
F43 C62 C61 118.1(3) . . ?
C63 C62 C61 123.6(3) . . ?
C64 C63 C62 116.0(3) . . ?
C64 C63 H63 122.0 . . ?
C62 C63 H63 122.0 . . ?
C63 C64 F44 118.5(3) . . ?
C63 C64 C65 123.5(3) . . ?
F44 C64 C65 118.0(3) . . ?
C64 C65 C60 120.2(3) . . ?
C64 C65 H65 119.9 . . ?
C60 C65 H65 119.9 . . ?
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 C16 1.361(4) . ?
F2 C18 1.360(3) . ?
F3 C22 1.346(6) . ?
F4 C24 1.361(6) . ?
C1 C2 1.376(4) . ?
C1 C10 1.386(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.408(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 C14 1.491(4) . ?
C4 C11 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(4) . ?
C5 C12 1.401(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.407(4) . ?
C6 C20 1.486(3) . ?
C7 C8 1.368(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.378(4) . ?
C8 H8 0.9300 . ?
N9 C13 1.374(3) . ?
N9 C10 1.383(4) . ?
N9 H9 0.85(4) . ?
C10 C11 1.415(3) . ?
C11 C12 1.440(3) . ?
C12 C13 1.420(3) . ?
C14 C15 1.393(4) . ?
C14 C19 1.399(3) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C17 C18 1.362(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(5) . ?
C20 C25 1.399(5) . ?
C21 C22 1.386(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(8) . ?
C23 C24 1.365(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(4) . ?
C25 H25 0.9300 . ?
N31 C31 1.442(4) . ?
N31 C35 1.469(4) . ?
N31 C33 1.470(5) . ?
C31 C32 1.537(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N32 1.453(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.543(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 N32 1.432(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.536(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 N32 1.468(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
F41 C56 1.338(5) . ?
F42 C58 1.366(5) . ?
F43 C62 1.342(4) . ?
F44 C64 1.353(4) . ?
C41 C42 1.381(4) . ?
C41 C50 1.397(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.405(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.396(3) . ?
C43 C54 1.490(3) . ?
C44 C51 1.391(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.387(3) . ?
C45 C52 1.391(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.412(3) . ?
C46 C60 1.487(3) . ?
C47 C48 1.373(4) . ?
C47 H47 0.9300 . ?
C48 C53 1.388(4) . ?
C48 H48 0.9300 . ?
N49 C50 1.373(3) . ?
N49 C53 1.380(3) . ?
N49 H49 0.96(4) . ?
C50 C51 1.407(3) . ?
C51 C52 1.449(3) . ?
C52 C53 1.411(3) . ?
C54 C59 1.393(4) . ?
C54 C55 1.394(5) . ?
C55 C56 1.376(4) . ?
C55 H55 0.9300 . ?
C56 C57 1.370(7) . ?
C57 C58 1.377(7) . ?
C57 H57 0.9300 . ?
C58 C59 1.377(4) . ?
C59 H59 0.9300 . ?
C60 C65 1.389(3) . ?
C60 C61 1.391(4) . ?
C61 C62 1.381(4) . ?
C61 H61 0.9300 . ?
C62 C63 1.362(5) . ?
C63 C64 1.346(5) . ?
C63 H63 0.9300 . ?
C64 C65 1.376(4) . ?
C65 H65 0.9300 . ?
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 0.85(4) 2.06(4) 2.884(3) 163(4) . yes
C15 H15 F4 0.93 2.59 3.377(4) 143.0 4_454 yes
C33 H33A F44 0.97 2.61 3.288(5) 127.5 2_575 yes
N49 H49 N32 0.96(4) 1.94(4) 2.875(3) 164(4) . 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 1.7(5) . . . . ?
C1 C2 C3 C4 -1.9(5) . . . . ?
C1 C2 C3 C14 178.4(3) . . . . ?
C2 C3 C4 C11 0.5(4) . . . . ?
C14 C3 C4 C11 -179.7(3) . . . . ?
C12 C5 C6 C7 1.0(5) . . . . ?
C12 C5 C6 C20 -178.1(3) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
C20 C6 C7 C8 178.5(3) . . . . ?
C6 C7 C8 C13 -0.3(6) . . . . ?
C13 N9 C10 C1 -178.1(3) . . . . ?
C13 N9 C10 C11 1.4(4) . . . . ?
C2 C1 C10 N9 179.3(3) . . . . ?
C2 C1 C10 C11 -0.1(5) . . . . ?
C3 C4 C11 C10 0.9(4) . . . . ?
C3 C4 C11 C12 -178.0(3) . . . . ?
N9 C10 C11 C4 179.3(3) . . . . ?
C1 C10 C11 C4 -1.1(5) . . . . ?
N9 C10 C11 C12 -1.5(3) . . . . ?
C1 C10 C11 C12 178.0(3) . . . . ?
C6 C5 C12 C13 -0.4(4) . . . . ?
C6 C5 C12 C11 177.6(3) . . . . ?
C4 C11 C12 C5 2.0(6) . . . . ?
C10 C11 C12 C5 -177.0(3) . . . . ?
C4 C11 C12 C13 -179.9(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C10 N9 C13 C8 178.0(4) . . . . ?
C10 N9 C13 C12 -0.7(4) . . . . ?
C7 C8 C13 N9 -177.6(4) . . . . ?
C7 C8 C13 C12 0.9(5) . . . . ?
C5 C12 C13 N9 178.2(3) . . . . ?
C11 C12 C13 N9 -0.3(3) . . . . ?
C5 C12 C13 C8 -0.6(5) . . . . ?
C11 C12 C13 C8 -179.1(3) . . . . ?
C4 C3 C14 C15 163.3(3) . . . . ?
C2 C3 C14 C15 -17.0(5) . . . . ?
C4 C3 C14 C19 -18.0(4) . . . . ?
C2 C3 C14 C19 161.7(3) . . . . ?
C19 C14 C15 C16 0.4(5) . . . . ?
C3 C14 C15 C16 179.1(3) . . . . ?
C14 C15 C16 F1 179.5(3) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
F1 C16 C17 C18 -179.4(4) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C16 C17 C18 F2 -179.5(4) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
F2 C18 C19 C14 -179.3(3) . . . . ?
C17 C18 C19 C14 1.9(6) . . . . ?
C15 C14 C19 C18 -1.7(5) . . . . ?
C3 C14 C19 C18 179.6(3) . . . . ?
C5 C6 C20 C21 -151.7(3) . . . . ?
C7 C6 C20 C21 29.2(5) . . . . ?
C5 C6 C20 C25 29.3(5) . . . . ?
C7 C6 C20 C25 -149.8(3) . . . . ?
C25 C20 C21 C22 0.4(5) . . . . ?
C6 C20 C21 C22 -178.6(3) . . . . ?
C20 C21 C22 F3 179.8(4) . . . . ?
C20 C21 C22 C23 -0.3(6) . . . . ?
F3 C22 C23 C24 179.3(5) . . . . ?
C21 C22 C23 C24 -0.6(7) . . . . ?
C22 C23 C24 F4 -179.1(4) . . . . ?
C22 C23 C24 C25 1.5(7) . . . . ?
F4 C24 C25 C20 179.2(4) . . . . ?
C23 C24 C25 C20 -1.4(6) . . . . ?
C21 C20 C25 C24 0.4(5) . . . . ?
C6 C20 C25 C24 179.4(3) . . . . ?
C35 N31 C31 C32 57.3(4) . . . . ?
C33 N31 C31 C32 -60.3(3) . . . . ?
N31 C31 C32 N32 2.2(4) . . . . ?
C31 N31 C33 C34 59.7(3) . . . . ?
C35 N31 C33 C34 -58.3(4) . . . . ?
N31 C33 C34 N32 -0.7(4) . . . . ?
C31 N31 C35 C36 -59.7(4) . . . . ?
C33 N31 C35 C36 57.5(4) . . . . ?
N31 C35 C36 N32 1.7(5) . . . . ?
C33 C34 N32 C32 -58.1(3) . . . . ?
C33 C34 N32 C36 60.7(4) . . . . ?
C31 C32 N32 C34 57.7(3) . . . . ?
C31 C32 N32 C36 -60.6(4) . . . . ?
C35 C36 N32 C34 -61.3(4) . . . . ?
C35 C36 N32 C32 57.9(4) . . . . ?
C50 C41 C42 C43 0.3(5) . . . . ?
C41 C42 C43 C44 0.3(5) . . . . ?
C41 C42 C43 C54 -180.0(3) . . . . ?
C42 C43 C44 C51 -0.7(5) . . . . ?
C54 C43 C44 C51 179.6(3) . . . . ?
C52 C45 C46 C47 0.4(4) . . . . ?
C52 C45 C46 C60 179.6(3) . . . . ?
C45 C46 C47 C48 -2.2(5) . . . . ?
C60 C46 C47 C48 178.5(3) . . . . ?
C46 C47 C48 C53 1.9(5) . . . . ?
C53 N49 C50 C41 178.6(3) . . . . ?
C53 N49 C50 C51 0.7(4) . . . . ?
C42 C41 C50 N49 -178.1(3) . . . . ?
C42 C41 C50 C51 -0.4(5) . . . . ?
C43 C44 C51 C50 0.5(4) . . . . ?
C43 C44 C51 C52 178.6(3) . . . . ?
N49 C50 C51 C44 178.1(3) . . . . ?
C41 C50 C51 C44 0.0(5) . . . . ?
N49 C50 C51 C52 -0.4(3) . . . . ?
C41 C50 C51 C52 -178.5(3) . . . . ?
C46 C45 C52 C53 1.7(4) . . . . ?
C46 C45 C52 C51 179.6(3) . . . . ?
C44 C51 C52 C45 3.6(6) . . . . ?
C50 C51 C52 C45 -178.2(3) . . . . ?
C44 C51 C52 C53 -178.3(3) . . . . ?
C50 C51 C52 C53 -0.1(3) . . . . ?
C50 N49 C53 C48 -179.6(3) . . . . ?
C50 N49 C53 C52 -0.8(4) . . . . ?
C47 C48 C53 N49 179.0(3) . . . . ?
C47 C48 C53 C52 0.3(5) . . . . ?
C45 C52 C53 N49 178.9(3) . . . . ?
C51 C52 C53 N49 0.5(3) . . . . ?
C45 C52 C53 C48 -2.1(5) . . . . ?
C51 C52 C53 C48 179.5(3) . . . . ?
C44 C43 C54 C59 32.9(5) . . . . ?
C42 C43 C54 C59 -146.9(3) . . . . ?
C44 C43 C54 C55 -146.7(3) . . . . ?
C42 C43 C54 C55 33.6(5) . . . . ?
C59 C54 C55 C56 0.8(5) . . . . ?
C43 C54 C55 C56 -179.6(3) . . . . ?
C54 C55 C56 F41 179.7(4) . . . . ?
C54 C55 C56 C57 -0.6(6) . . . . ?
F41 C56 C57 C58 179.8(4) . . . . ?
C55 C56 C57 C58 0.0(7) . . . . ?
C56 C57 C58 F42 -178.3(4) . . . . ?
C56 C57 C58 C59 0.4(7) . . . . ?
F42 C58 C59 C54 178.5(3) . . . . ?
C57 C58 C59 C54 -0.2(6) . . . . ?
C55 C54 C59 C58 -0.4(5) . . . . ?
C43 C54 C59 C58 180.0(3) . . . . ?
C45 C46 C60 C65 -8.9(5) . . . . ?
C47 C46 C60 C65 170.3(3) . . . . ?
C45 C46 C60 C61 171.1(3) . . . . ?
C47 C46 C60 C61 -9.7(5) . . . . ?
C65 C60 C61 C62 0.1(6) . . . . ?
C46 C60 C61 C62 -179.9(3) . . . . ?
C60 C61 C62 F43 179.3(4) . . . . ?
C60 C61 C62 C63 -1.1(7) . . . . ?
F43 C62 C63 C64 -178.6(5) . . . . ?
C61 C62 C63 C64 1.9(7) . . . . ?
C62 C63 C64 F44 179.5(4) . . . . ?
C62 C63 C64 C65 -1.7(6) . . . . ?
C63 C64 C65 C60 0.8(6) . . . . ?
F44 C64 C65 C60 179.6(4) . . . . ?
C61 C60 C65 C64 0.1(5) . . . . ?
C46 C60 C65 C64 -180.0(3) . . . . ?
