#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:53:59 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267084 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/97/1559774.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_1559774
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                 95.7754(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7928(4)
_cell_length_b                   14.5649(8)
_cell_length_c                   21.3902(12)
_cell_measurement_reflns_used    8413
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      2.37
_cell_volume                     2105.5(2)
_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      200(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_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  0.0866
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            29489
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.095
_diffrn_reflns_theta_min         2.370
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       prism
_exptl_crystal_F_000             924
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6161
_refine_ls_number_restraints     342
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1748
_refine_ls_R_factor_gt           0.0596
_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)+(0.0474P)²+0.2656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2751
_reflns_number_total             6161
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05899h2.cif
_cod_data_source_block           ANH-BRM-3I-200K
_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               1559774
_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   0.960
_shelx_estimated_absorpt_t_max   0.978
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
F3 F 1.44316(18) 0.55398(12) 0.40704(7) 0.0762(6) Uani 0.914(2) 1 d D . P A 1
F4 F 1.5410(2) 0.63005(13) 0.51746(7) 0.0973(6) Uani 1 1 d D . . B 1
F3B F 0.7790(17) 0.6479(15) 0.4228(8) 0.098(7) Uani 0.086(2) 1 d D . P A 2
F2 F 0.0505(2) 0.15847(10) 0.40913(6) 0.0685(4) Uani 1 1 d D . . . .
F1 F 0.35009(18) 0.24359(9) 0.36748(6) 0.0537(4) Uani 0.914(2) 1 d D . P A 1
F1B F -0.007(2) 0.2568(10) 0.1628(4) 0.062(4) Uani 0.086(2) 1 d D . P A 2
C1 C 0.5246(3) 0.34695(14) 0.14986(10) 0.0427(5) Uani 1 1 d . . . . .
H1 H 0.539646 0.340344 0.106408 0.051 Uiso 1 1 calc R U . . .
C2 C 0.3714(3) 0.30448(14) 0.17631(10) 0.0411(5) Uani 1 1 d . . . . .
H2 H 0.281636 0.267333 0.150441 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3435(3) 0.31423(13) 0.23998(9) 0.0347(5) Uani 1 1 d . . . . .
C4 C 0.4741(3) 0.36869(13) 0.27786(9) 0.0339(5) Uani 1 1 d . . . . .
H4 H 0.455428 0.377222 0.320901 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8625(3) 0.49574(13) 0.33920(9) 0.0344(5) Uani 1 1 d . . . . .
H5 H 0.784482 0.484367 0.372827 0.041 Uiso 1 1 calc R U . . .
C6 C 1.0389(3) 0.54400(13) 0.35015(10) 0.0365(5) Uani 1 1 d . . . . .
C7 C 1.1527(3) 0.55855(13) 0.29965(10) 0.0389(5) Uani 1 1 d . . . . .
H7 H 1.274450 0.590674 0.307191 0.047 Uiso 1 1 calc R U . . .
C8 C 1.0947(3) 0.52821(13) 0.23992(10) 0.0404(5) Uani 1 1 d . . . . .
H8 H 1.173800 0.539212 0.206499 0.048 Uiso 1 1 calc R U . . .
N9 N 0.8270(2) 0.44362(11) 0.17528(8) 0.0403(4) Uani 1 1 d . . . . .
H9 H 0.873(3) 0.4475(13) 0.1333(10) 0.048 Uiso 1 1 d . U . . .
C10 C 0.6557(3) 0.39943(13) 0.18857(9) 0.0365(5) Uani 1 1 d . . . . .
C11 C 0.6322(3) 0.41074(13) 0.25272(9) 0.0326(5) Uani 1 1 d . . . . .
C12 C 0.8000(3) 0.46412(12) 0.27937(9) 0.0321(4) Uani 1 1 d . . . . .
C13 C 0.9173(3) 0.48102(13) 0.22988(9) 0.0343(5) Uani 1 1 d . . . . .
C14 C 0.1759(3) 0.26564(13) 0.26540(10) 0.0354(5) Uani 1 1 d . . . . .
C15 C 0.1848(3) 0.23411(13) 0.32644(10) 0.0384(5) Uani 1 1 d D . . . .
H15 H 0.301293 0.244666 0.353945 0.046 Uiso 0.086(2) 1 calc R U P A 2
C16 C 0.0296(3) 0.18787(14) 0.34849(10) 0.0452(5) Uani 1 1 d D . . . .
C17 C -0.1405(3) 0.17021(15) 0.31153(12) 0.0497(6) Uani 1 1 d . . . . .
H17 H -0.246759 0.138547 0.327629 0.060 Uiso 1 1 calc R U . . .
C18 C -0.1545(3) 0.19933(14) 0.25042(12) 0.0491(6) Uani 1 1 d . . . . .
H18 H -0.271153 0.187063 0.223342 0.059 Uiso 1 1 calc R U . . .
C19 C 0.0004(3) 0.24655(14) 0.22789(11) 0.0427(5) Uani 1 1 d D . . . .
H19 H -0.012291 0.266251 0.186538 0.051 Uiso 0.914(2) 1 d R U P A 1
C20 C 1.0997(3) 0.58249(13) 0.41305(9) 0.0379(5) Uani 1 1 d . . . . .
C21 C 1.2942(3) 0.58822(16) 0.43866(11) 0.0498(6) Uani 1 1 d D . . . .
H21 H 1.395078 0.564537 0.415471 0.060 Uiso 0.086(2) 1 calc R U P A 2
C22 C 1.3469(3) 0.62687(18) 0.49634(12) 0.0562(6) Uani 1 1 d D . . . .
C23 C 1.2108(3) 0.66153(16) 0.53204(11) 0.0565(6) Uani 1 1 d . . . . .
H23 H 1.249022 0.688683 0.571796 0.068 Uiso 1 1 calc R U . . .
C24 C 1.0148(3) 0.65588(17) 0.50843(11) 0.0594(7) Uani 1 1 d . . . . .
H24 H 0.915145 0.678435 0.532549 0.071 Uiso 1 1 calc R U . . .
C25 C 0.9623(3) 0.61808(16) 0.45054(10) 0.0499(6) Uani 1 1 d D . . . .
H25 H 0.829721 0.615719 0.435866 0.060 Uiso 0.914(2) 1 d R U P A 1
N31 N 0.961(3) 0.4657(16) 0.0558(9) 0.055(3) Uani 0.5 1 d . . P C -1
C31 C 0.9195(8) 0.5766(4) 0.0455(2) 0.0629(14) Uani 0.5 1 d . . P C -1
H31A H 0.777525 0.589110 0.048452 0.076 Uiso 0.5 1 calc R U P C -1
H31B H 0.996469 0.610858 0.079692 0.076 Uiso 0.5 1 calc R U P C -1
C32 C 0.9759(8) 0.6119(3) -0.0181(2) 0.0596(13) Uani 0.5 1 d . . P C -1
H32A H 1.079607 0.655958 -0.011324 0.072 Uiso 0.5 1 d R U P C -1
H32B H 0.865480 0.639444 -0.042054 0.072 Uiso 0.5 1 d R U P C -1
C33 C 0.8259(8) 0.4330(4) 0.0001(2) 0.0656(14) Uani 0.5 1 d . . P C -1
H33A H 0.689554 0.447735 0.004921 0.079 Uiso 0.5 1 d R U P C -1
H33B H 0.839459 0.367247 0.001321 0.079 Uiso 0.5 1 d R U P C -1
C34 C 0.8833(8) 0.4677(4) -0.0643(2) 0.0572(13) Uani 0.5 1 d . . P C -1
H34A H 0.774948 0.500975 -0.085010 0.069 Uiso 0.5 1 d R U P C -1
H34B H 0.913972 0.417786 -0.090530 0.069 Uiso 0.5 1 d R U P C -1
C35 C 1.1549(8) 0.4559(5) 0.0442(3) 0.0725(16) Uani 0.5 1 d . . P C -1
H35A H 1.188653 0.389793 0.046882 0.087 Uiso 0.5 1 calc R U P C -1
H35B H 1.238681 0.487554 0.078097 0.087 Uiso 0.5 1 calc R U P C -1
C36 C 1.2109(8) 0.4923(5) -0.0192(3) 0.0689(15) Uani 0.5 1 d . . P C -1
H36A H 1.265818 0.443772 -0.041957 0.083 Uiso 0.5 1 d R U P C -1
H36B H 1.307988 0.539373 -0.012067 0.083 Uiso 0.5 1 d R U P C -1
N32 N 1.053(3) 0.5232(16) -0.0504(8) 0.048(3) Uani 0.5 1 d . . P C -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 117.95(19) . . ?
C2 C1 H1 121.0 . . ?
C10 C1 H1 121.0 . . ?
C1 C2 C3 122.31(19) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 118.96(18) . . ?
C4 C3 C14 121.69(18) . . ?
C2 C3 C14 119.34(18) . . ?
C3 C4 C11 119.92(18) . . ?
C3 C4 H4 120.0 . . ?
C11 C4 H4 120.0 . . ?
C12 C5 C6 120.20(17) . . ?
C12 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 118.58(19) . . ?
C5 C6 C20 120.18(17) . . ?
C7 C6 C20 121.18(17) . . ?
C8 C7 C6 122.60(18) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C13 117.90(17) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
C13 N9 C10 108.79(16) . . ?
C13 N9 H9 126.9(11) . . ?
C10 N9 H9 124.3(11) . . ?
C1 C10 N9 129.62(18) . . ?
C1 C10 C11 121.27(17) . . ?
N9 C10 C11 109.03(18) . . ?
C4 C11 C10 119.56(18) . . ?
C4 C11 C12 133.79(18) . . ?
C10 C11 C12 106.54(16) . . ?
C5 C12 C13 119.43(17) . . ?
C5 C12 C11 134.25(17) . . ?
C13 C12 C11 106.28(17) . . ?
N9 C13 C8 129.40(17) . . ?
N9 C13 C12 109.32(17) . . ?
C8 C13 C12 121.28(18) . . ?
C15 C14 C19 115.54(18) . . ?
C15 C14 C3 122.79(18) . . ?
C19 C14 C3 121.64(19) . . ?
F1 C15 C16 116.10(19) . . ?
F1 C15 C14 122.11(17) . . ?
C16 C15 C14 121.74(19) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C17 C16 F2 119.80(19) . . ?
C17 C16 C15 122.0(2) . . ?
F2 C16 C15 118.2(2) . . ?
C16 C17 C18 118.1(2) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 122.3(2) . . ?
C18 C19 F1B 116.6(6) . . ?
C14 C19 F1B 119.7(6) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 118.6 . . ?
C21 C20 C25 114.82(19) . . ?
C21 C20 C6 123.53(18) . . ?
C25 C20 C6 121.63(18) . . ?
F3 C21 C22 117.15(19) . . ?
F3 C21 C20 120.5(2) . . ?
C22 C21 C20 122.31(19) . . ?
C22 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
F4 C22 C23 119.8(2) . . ?
F4 C22 C21 118.2(2) . . ?
C23 C22 C21 122.0(2) . . ?
C22 C23 C24 117.4(2) . . ?
C22 C23 H23 121.3 . . ?
C24 C23 H23 121.3 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C20 122.9(2) . . ?
C24 C25 F3B 113.6(8) . . ?
C20 C25 F3B 119.5(7) . . ?
C24 C25 H25 118.6 . . ?
C20 C25 H25 118.6 . . ?
C35 N31 C33 110.1(14) . . ?
C35 N31 C31 103.3(15) . . ?
C33 N31 C31 97.0(12) . . ?
C32 C31 N31 113.0(7) . . ?
C32 C31 H31A 109.0 . . ?
N31 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
N31 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 N32 103.7(7) . . ?
C31 C32 H32A 109.6 . . ?
N32 C32 H32A 110.1 . . ?
C31 C32 H32B 111.3 . . ?
N32 C32 H32B 112.9 . . ?
H32A C32 H32B 109.1 . . ?
N31 C33 C34 114.3(9) . . ?
N31 C33 H33A 111.1 . . ?
C34 C33 H33A 110.6 . . ?
N31 C33 H33B 104.1 . . ?
C34 C33 H33B 108.4 . . ?
H33A C33 H33B 108.0 . . ?
N32 C34 C33 105.8(8) . . ?
N32 C34 H34A 112.6 . . ?
C33 C34 H34A 109.1 . . ?
N32 C34 H34B 109.6 . . ?
C33 C34 H34B 111.2 . . ?
H34A C34 H34B 108.5 . . ?
N31 C35 C36 116.8(9) . . ?
N31 C35 H35A 108.1 . . ?
C36 C35 H35A 108.1 . . ?
N31 C35 H35B 108.1 . . ?
C36 C35 H35B 108.1 . . ?
H35A C35 H35B 107.3 . . ?
N32 C36 C35 108.2(8) . . ?
N32 C36 H36A 110.0 . . ?
C35 C36 H36A 109.8 . . ?
N32 C36 H36B 110.9 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.3 . . ?
C36 N32 C34 121.9(17) . . ?
C36 N32 C32 110.9(14) . . ?
C34 N32 C32 104.9(12) . . ?
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
F3 C21 1.366(2) . ?
F4 C22 1.351(2) . ?
F3B C25 1.394(7) . ?
F2 C16 1.360(2) . ?
F1 C15 1.361(2) . ?
F1B C19 1.397(7) . ?
C1 C2 1.380(3) . ?
C1 C10 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 C14 1.489(3) . ?
C4 C11 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C12 1.386(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(3) . ?
C6 C20 1.477(3) . ?
C7 C8 1.371(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.385(3) . ?
C8 H8 0.9500 . ?
N9 C13 1.376(2) . ?
N9 C10 1.384(2) . ?
N9 H9 0.98(2) . ?
C10 C11 1.407(3) . ?
C11 C12 1.448(3) . ?
C12 C13 1.409(2) . ?
C14 C15 1.379(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.374(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.357(3) . ?
C17 C18 1.368(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9257 . ?
C20 C21 1.381(3) . ?
C20 C25 1.390(3) . ?
C21 C22 1.371(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.354(3) . ?
C23 C24 1.378(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.369(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9238 . ?
N31 C35 1.37(2) . ?
N31 C33 1.50(2) . ?
N31 C31 1.65(2) . ?
C31 C32 1.539(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.58(2) . ?
C32 H32A 0.9537 . ?
C32 H32B 0.9527 . ?
C33 C34 1.553(6) . ?
C33 H33A 0.9661 . ?
C33 H33B 0.9624 . ?
C34 N32 1.42(2) . ?
C34 H34A 0.9527 . ?
C34 H34B 0.9548 . ?
C35 C36 1.538(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.28(2) . ?
C36 H36A 0.9553 . ?
C36 H36B 0.9532 . ?
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 0.98(2) 1.84(3) 2.817(19) 174.9(19) . yes
N9 H9 N32 0.98(2) 1.94(3) 2.909(16) 170.1(18) 3_765 yes
C24 H24 F4 0.95 2.63 3.265(3) 125.0 1_455 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 1.1(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C14 -179.43(18) . . . . ?
C2 C3 C4 C11 -1.5(3) . . . . ?
C14 C3 C4 C11 178.09(17) . . . . ?
C12 C5 C6 C7 -1.0(3) . . . . ?
C12 C5 C6 C20 176.34(18) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C20 C6 C7 C8 -176.23(19) . . . . ?
C6 C7 C8 C13 -0.4(3) . . . . ?
C2 C1 C10 N9 175.22(19) . . . . ?
C2 C1 C10 C11 -1.1(3) . . . . ?
C13 N9 C10 C1 -175.0(2) . . . . ?
C13 N9 C10 C11 1.6(2) . . . . ?
C3 C4 C11 C10 1.5(3) . . . . ?
C3 C4 C11 C12 -174.12(19) . . . . ?
C1 C10 C11 C4 -0.2(3) . . . . ?
N9 C10 C11 C4 -177.19(17) . . . . ?
C1 C10 C11 C12 176.53(18) . . . . ?
N9 C10 C11 C12 -0.5(2) . . . . ?
C6 C5 C12 C13 0.3(3) . . . . ?
C6 C5 C12 C11 177.75(19) . . . . ?
C4 C11 C12 C5 -2.5(4) . . . . ?
C10 C11 C12 C5 -178.5(2) . . . . ?
C4 C11 C12 C13 175.2(2) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C10 N9 C13 C8 177.35(19) . . . . ?
C10 N9 C13 C12 -2.2(2) . . . . ?
C7 C8 C13 N9 -179.81(19) . . . . ?
C7 C8 C13 C12 -0.3(3) . . . . ?
C5 C12 C13 N9 179.95(17) . . . . ?
C11 C12 C13 N9 1.8(2) . . . . ?
C5 C12 C13 C8 0.4(3) . . . . ?
C11 C12 C13 C8 -177.73(17) . . . . ?
C4 C3 C14 C15 -31.3(3) . . . . ?
C2 C3 C14 C15 148.3(2) . . . . ?
C4 C3 C14 C19 150.72(19) . . . . ?
C2 C3 C14 C19 -29.7(3) . . . . ?
C19 C14 C15 F1 176.64(17) . . . . ?
C3 C14 C15 F1 -1.5(3) . . . . ?
C19 C14 C15 C16 -0.6(3) . . . . ?
C3 C14 C15 C16 -178.70(18) . . . . ?
F1 C15 C16 C17 -177.09(19) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
F1 C15 C16 F2 2.2(3) . . . . ?
C14 C15 C16 F2 179.56(18) . . . . ?
F2 C16 C17 C18 -178.76(19) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C14 0.7(3) . . . . ?
C17 C18 C19 F1B 166.9(7) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C3 C14 C19 C18 178.25(18) . . . . ?
C15 C14 C19 F1B -165.7(8) . . . . ?
C3 C14 C19 F1B 12.4(8) . . . . ?
C5 C6 C20 C21 145.6(2) . . . . ?
C7 C6 C20 C21 -37.2(3) . . . . ?
C5 C6 C20 C25 -36.0(3) . . . . ?
C7 C6 C20 C25 141.2(2) . . . . ?
C25 C20 C21 F3 178.7(2) . . . . ?
C6 C20 C21 F3 -2.8(3) . . . . ?
C25 C20 C21 C22 -0.6(3) . . . . ?
C6 C20 C21 C22 177.9(2) . . . . ?
F3 C21 C22 F4 1.2(4) . . . . ?
C20 C21 C22 F4 -179.6(2) . . . . ?
F3 C21 C22 C23 -178.9(2) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
F4 C22 C23 C24 -179.5(2) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C23 C24 C25 C20 1.0(4) . . . . ?
C23 C24 C25 F3B -156.3(10) . . . . ?
C21 C20 C25 C24 -0.1(3) . . . . ?
C6 C20 C25 C24 -178.6(2) . . . . ?
C21 C20 C25 F3B 155.9(11) . . . . ?
C6 C20 C25 F3B -22.6(11) . . . . ?
C35 N31 C31 C32 52.6(14) . . . . ?
C33 N31 C31 C32 -60.0(12) . . . . ?
N31 C31 C32 N32 0.4(6) . . . . ?
C35 N31 C33 C34 -45.6(18) . . . . ?
C31 N31 C33 C34 61.4(12) . . . . ?
N31 C33 C34 N32 -0.5(7) . . . . ?
C33 N31 C35 C36 48.3(19) . . . . ?
C31 N31 C35 C36 -54.5(15) . . . . ?
N31 C35 C36 N32 -2.2(9) . . . . ?
C35 C36 N32 C34 -56.4(16) . . . . ?
C35 C36 N32 C32 67.6(14) . . . . ?
C33 C34 N32 C36 56.6(15) . . . . ?
C33 C34 N32 C32 -70.1(12) . . . . ?
C31 C32 N32 C36 -64.3(13) . . . . ?
C31 C32 N32 C34 69.0(11) . . . . ?
