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#$Date: 2024-09-06 02:20:09 +0200 (Fri 06 de Sep de 2024) $
#$Revision: 294531 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/90/7249099.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_7249099
loop_
_publ_author_name
'Vaganova, Tamara'
'Gatilov, Yurij'
'Kryuchkova, Natalia'
'Pishchur, Denis'
'Malykhin, Evgenij'
_publ_section_title
;
 Competition of intermolecular interactions in the self-assembly of
 co-crystals of trifluoro-meta-arylenediamines (benzene, nitrobenzene,
 pyridine) with 12-, 15-, and 18-membered crown ethers
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              4602
_journal_page_last               4616
_journal_paper_doi               10.1039/D4CE00612G
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '2(C6 H4 F3 N3 O2), C8 H16 O4'
_chemical_formula_sum            'C20 H24 F6 N6 O8'
_chemical_formula_weight         590.45
_chemical_melting_point          403
_chemical_name_systematic
;
Co-crystal of 2,4-diaminotrifluoronitrobenzene and 12-crown-4, 2:1
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-06-14 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.584(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4617(18)
_cell_length_b                   21.673(3)
_cell_length_c                   7.3234(8)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.77
_cell_measurement_theta_min      2.63
_cell_volume                     2454.0(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.1265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            43266
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.219
_diffrn_reflns_theta_min         1.317
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.8028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       prismoid
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.363
_refine_ls_R_factor_all          0.1992
_refine_ls_R_factor_gt           0.1404
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4282
_refine_ls_wR_factor_ref         0.4467
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2325
_reflns_number_total             4876
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00612g2.cif
_cod_data_source_block           t7021_4_2C12cr4
_cod_depositor_comments
'Adding full bibliography for 7249096--7249100.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249099
_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   0.908
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.8143(3) 0.60683(18) 0.4164(6) 0.0607(13) Uani 1 1 d . . . . .
N1 N 0.7083(5) 0.8112(3) 0.5182(10) 0.0602(19) Uani 1 1 d . . . . .
C1 C 0.7730(5) 0.7710(3) 0.4572(10) 0.0414(17) Uani 1 1 d . . . . .
O1 O 0.6371(5) 0.7930(3) 0.5550(11) 0.093(2) Uani 1 1 d . . . . .
N2 N 0.6834(4) 0.6786(3) 0.5121(10) 0.0595(18) Uani 1 1 d . . . . .
H2A H 0.678499 0.639042 0.512029 0.071 Uiso 1 1 calc R U . . .
H2B H 0.640616 0.701200 0.544901 0.071 Uiso 1 1 calc R U . . .
F2 F 0.9937(3) 0.7760(2) 0.2937(8) 0.0794(17) Uani 1 1 d . . . . .
O2 O 0.7241(5) 0.8668(3) 0.5322(12) 0.093(2) Uani 1 1 d . . . . .
C2 C 0.7581(5) 0.7050(3) 0.4609(10) 0.0450(18) Uani 1 1 d . . . . .
N3 N 0.9714(5) 0.6512(3) 0.3069(11) 0.071(2) Uani 1 1 d . . . . .
H3A H 0.963549 0.611902 0.308671 0.085 Uiso 1 1 calc R U . . .
H3B H 1.020503 0.666023 0.274415 0.085 Uiso 1 1 calc R U . . .
F3 F 0.8688(4) 0.8531(2) 0.3836(8) 0.0796(17) Uani 1 1 d . . . . .
C3 C 0.8270(5) 0.6697(3) 0.4082(10) 0.0453(18) Uani 1 1 d . . . . .
C4 C 0.9067(5) 0.6895(3) 0.3551(10) 0.0446(18) Uani 1 1 d . . . . .
C5 C 0.9178(5) 0.7537(4) 0.3539(12) 0.052(2) Uani 1 1 d . . . . .
C6 C 0.8535(5) 0.7922(3) 0.4009(11) 0.053(2) Uani 1 1 d . . . . .
O5 O 0.5098(5) 0.5121(3) 0.2466(8) 0.080(2) Uani 1 1 d . . . . .
O6 O 0.3690(5) 0.4501(3) 0.4604(12) 0.106(3) Uani 1 1 d . . . . .
C13 C 0.4768(10) 0.4558(5) 0.2195(17) 0.119(5) Uani 1 1 d . . . . .
H13A H 0.502754 0.426374 0.303636 0.142 Uiso 1 1 calc R U . . .
H13B H 0.487349 0.442065 0.095647 0.142 Uiso 1 1 calc R U . . .
C14 C 0.3823(6) 0.4614(5) 0.2525(12) 0.072(3) Uani 1 1 d . . . . .
H14A H 0.350642 0.430997 0.181139 0.086 Uiso 1 1 calc R U . . .
H14B H 0.361998 0.502154 0.218386 0.086 Uiso 1 1 calc R U . . .
C15 C 0.3571(8) 0.5051(5) 0.5523(17) 0.100(4) Uani 1 1 d . . . . .
H15A H 0.296268 0.515881 0.558080 0.120 Uiso 1 1 calc R U . . .
H15B H 0.388476 0.538529 0.494999 0.120 Uiso 1 1 calc R U . . .
C16 C 0.3923(7) 0.4912(5) 0.7336(14) 0.083(3) Uani 1 1 d . . . . .
H16A H 0.368657 0.451974 0.772419 0.100 Uiso 1 1 calc R U . . .
H16B H 0.371545 0.522388 0.817423 0.100 Uiso 1 1 calc R U . . .
O7 O -0.1211(4) 1.0505(3) 0.4620(9) 0.0755(19) Uani 1 1 d . . . . .
O8 O -0.0264(5) 0.9857(3) 0.7650(8) 0.0731(19) Uani 1 1 d . . . . .
C17 C -0.1584(6) 1.0152(6) 0.5944(14) 0.090(4) Uani 1 1 d . . . . .
H17A H -0.157599 0.972044 0.559548 0.108 Uiso 1 1 calc R U . . .
H17B H -0.217960 1.027682 0.612062 0.108 Uiso 1 1 calc R U . . .
C18 C -0.1071(6) 1.0247(5) 0.7657(12) 0.071(3) Uani 1 1 d . . . . .
H18A H -0.091329 1.067908 0.776672 0.085 Uiso 1 1 calc R U . . .
H18B H -0.142024 1.013864 0.870146 0.085 Uiso 1 1 calc R U . . .
C19 C 0.0448(6) 1.0195(5) 0.7439(15) 0.083(3) Uani 1 1 d . . . . .
H19A H 0.052384 1.046095 0.849459 0.100 Uiso 1 1 calc R U . . .
H19B H 0.037658 1.045700 0.637300 0.100 Uiso 1 1 calc R U . . .
C20 C 0.1209(6) 0.9822(4) 0.7225(11) 0.063(2) Uani 1 1 d . . . . .
H20A H 0.123444 0.951728 0.819444 0.076 Uiso 1 1 calc R U . . .
H20B H 0.171868 1.008101 0.733152 0.076 Uiso 1 1 calc R U . . .
O3 O 0.1359(5) 0.7069(3) 0.4753(13) 0.102(3) Uani 1 1 d . . . . .
F4 F 0.3143(3) 0.89403(18) 0.6148(6) 0.0591(13) Uani 1 1 d . . . . .
O4 O 0.2227(5) 0.6334(3) 0.5125(13) 0.100(3) Uani 1 1 d . . . . .
N4 N 0.2060(5) 0.6884(3) 0.5233(9) 0.0562(18) Uani 1 1 d . . . . .
N5 N 0.1822(4) 0.8218(3) 0.5151(10) 0.063(2) Uani 1 1 d . . . . .
H5A H 0.178865 0.861380 0.508323 0.076 Uiso 1 1 calc R U . . .
H5B H 0.138343 0.799488 0.485047 0.076 Uiso 1 1 calc R U . . .
F5 F 0.4952(3) 0.7248(2) 0.7377(8) 0.0752(16) Uani 1 1 d . . . . .
N6 N 0.4731(4) 0.8492(3) 0.7254(10) 0.067(2) Uani 1 1 d . . . . .
H6A H 0.465644 0.888500 0.726494 0.080 Uiso 1 1 calc R U . . .
H6B H 0.522215 0.833761 0.757103 0.080 Uiso 1 1 calc R U . . .
F6 F 0.3696(3) 0.6477(2) 0.6515(8) 0.0794(17) Uani 1 1 d . . . . .
C7 C 0.2718(5) 0.7297(3) 0.5781(10) 0.0432(18) Uani 1 1 d . . . . .
C8 C 0.2572(4) 0.7945(3) 0.5737(11) 0.0443(18) Uani 1 1 d . . . . .
C9 C 0.3275(5) 0.8326(3) 0.6216(10) 0.0425(18) Uani 1 1 d . . . . .
C10 C 0.4076(4) 0.8117(3) 0.6740(10) 0.0447(18) Uani 1 1 d . . . . .
C11 C 0.4182(5) 0.7473(4) 0.6814(11) 0.050(2) Uani 1 1 d . . . . .
C12 C 0.3529(5) 0.7082(3) 0.6326(11) 0.051(2) Uani 1 1 d . . . . .
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'
O O 0.0106 0.0060 '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
O1 N1 O2 119.0(7) . . ?
O1 N1 C1 121.6(7) . . ?
O2 N1 C1 119.5(8) . . ?
C6 C1 N1 122.1(7) . . ?
C6 C1 C2 118.2(7) . . ?
N1 C1 C2 119.6(7) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C2 C3 120.8(7) . . ?
N2 C2 C1 124.2(7) . . ?
C3 C2 C1 115.0(7) . . ?
C4 N3 H3A 120.0 . . ?
C4 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C2 C3 C4 127.6(7) . . ?
C2 C3 F1 115.4(6) . . ?
C4 C3 F1 117.0(6) . . ?
N3 C4 C3 123.6(7) . . ?
N3 C4 C5 121.2(7) . . ?
C3 C4 C5 115.2(7) . . ?
C6 C5 F2 120.6(7) . . ?
C6 C5 C4 121.5(7) . . ?
F2 C5 C4 117.7(7) . . ?
C5 C6 F3 116.9(8) . . ?
C5 C6 C1 122.4(7) . . ?
F3 C6 C1 120.6(7) . . ?
C13 O5 C16 110.4(9) . 3_666 ?
C15 O6 C14 111.1(8) . . ?
O5 C13 C14 106.0(9) . . ?
O5 C13 H13A 110.5 . . ?
C14 C13 H13A 110.5 . . ?
O5 C13 H13B 110.5 . . ?
C14 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 O6 106.6(8) . . ?
C13 C14 H14A 110.4 . . ?
O6 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
O6 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
O6 C15 C16 102.3(10) . . ?
O6 C15 H15A 111.3 . . ?
C16 C15 H15A 111.3 . . ?
O6 C15 H15B 111.3 . . ?
C16 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C15 C16 O5 117.3(8) . 3_666 ?
C15 C16 H16A 108.0 . . ?
O5 C16 H16A 108.0 3_666 . ?
C15 C16 H16B 108.0 . . ?
O5 C16 H16B 108.0 3_666 . ?
H16A C16 H16B 107.2 . . ?
C17 O7 C20 111.9(8) . 3_576 ?
C19 O8 C18 112.1(7) . . ?
O7 C17 C18 107.1(9) . . ?
O7 C17 H17A 110.3 . . ?
C18 C17 H17A 110.3 . . ?
O7 C17 H17B 110.3 . . ?
C18 C17 H17B 110.3 . . ?
H17A C17 H17B 108.5 . . ?
O8 C18 C17 110.6(7) . . ?
O8 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
O8 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
O8 C19 C20 112.4(9) . . ?
O8 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
O8 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 O7 111.5(7) . 3_576 ?
C19 C20 H20A 109.3 . . ?
O7 C20 H20A 109.3 3_576 . ?
C19 C20 H20B 109.3 . . ?
O7 C20 H20B 109.3 3_576 . ?
H20A C20 H20B 108.0 . . ?
O3 N4 O4 119.7(7) . . ?
O3 N4 C7 121.1(7) . . ?
O4 N4 C7 118.9(7) . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C10 N6 H6A 120.0 . . ?
C10 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C12 C7 C8 118.6(7) . . ?
C12 C7 N4 121.0(7) . . ?
C8 C7 N4 120.4(7) . . ?
N5 C8 C9 118.3(7) . . ?
N5 C8 C7 124.7(7) . . ?
C9 C8 C7 116.9(6) . . ?
F4 C9 C10 118.3(6) . . ?
F4 C9 C8 117.1(6) . . ?
C10 C9 C8 124.7(6) . . ?
N6 C10 C9 123.6(7) . . ?
N6 C10 C11 120.0(7) . . ?
C9 C10 C11 116.3(6) . . ?
F5 C11 C12 120.4(7) . . ?
F5 C11 C10 118.2(7) . . ?
C12 C11 C10 121.3(7) . . ?
C11 C12 F6 116.0(7) . . ?
C11 C12 C7 122.1(7) . . ?
F6 C12 C7 121.8(7) . . ?
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 C3 1.378(8) . ?
N1 O1 1.203(9) . ?
N1 O2 1.233(9) . ?
N1 C1 1.403(10) . ?
C1 C6 1.394(11) . ?
C1 C2 1.448(10) . ?
N2 C2 1.346(9) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
F2 C5 1.348(9) . ?
C2 C3 1.370(10) . ?
N3 C4 1.351(10) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
F3 C6 1.346(8) . ?
C3 C4 1.366(10) . ?
C4 C5 1.401(11) . ?
C5 C6 1.345(11) . ?
O5 C13 1.337(14) . ?
O5 C16 1.520(12) 3_666 ?
O6 C15 1.383(12) . ?
O6 C14 1.558(12) . ?
C13 C14 1.488(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.461(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O7 C17 1.367(11) . ?
O7 C20 1.526(11) 3_576 ?
O8 C19 1.333(11) . ?
O8 C18 1.507(11) . ?
C17 C18 1.492(14) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.438(13) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
O3 N4 1.205(9) . ?
F4 C9 1.347(7) . ?
O4 N4 1.222(9) . ?
N4 C7 1.410(10) . ?
N5 C8 1.368(9) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
F5 C11 1.347(8) . ?
N6 C10 1.348(10) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
F6 C12 1.343(8) . ?
C7 C12 1.391(10) . ?
C7 C8 1.423(10) . ?
C8 C9 1.407(10) . ?
C9 C10 1.371(10) . ?
C10 C11 1.407(11) . ?
C11 C12 1.363(11) . ?
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
O1 N1 C1 C6 175.0(8) . . . . ?
O2 N1 C1 C6 -4.0(11) . . . . ?
O1 N1 C1 C2 -8.3(11) . . . . ?
O2 N1 C1 C2 172.7(7) . . . . ?
C6 C1 C2 N2 -179.9(7) . . . . ?
N1 C1 C2 N2 3.3(11) . . . . ?
C6 C1 C2 C3 0.4(10) . . . . ?
N1 C1 C2 C3 -176.5(7) . . . . ?
N2 C2 C3 C4 -179.2(7) . . . . ?
C1 C2 C3 C4 0.6(11) . . . . ?
N2 C2 C3 F1 -1.5(10) . . . . ?
C1 C2 C3 F1 178.2(6) . . . . ?
C2 C3 C4 N3 179.3(8) . . . . ?
F1 C3 C4 N3 1.7(11) . . . . ?
C2 C3 C4 C5 -0.5(11) . . . . ?
F1 C3 C4 C5 -178.1(6) . . . . ?
N3 C4 C5 C6 179.7(8) . . . . ?
C3 C4 C5 C6 -0.5(11) . . . . ?
N3 C4 C5 F2 3.5(11) . . . . ?
C3 C4 C5 F2 -176.7(7) . . . . ?
F2 C5 C6 F3 0.4(11) . . . . ?
C4 C5 C6 F3 -175.7(7) . . . . ?
F2 C5 C6 C1 177.5(7) . . . . ?
C4 C5 C6 C1 1.4(12) . . . . ?
N1 C1 C6 C5 175.4(7) . . . . ?
C2 C1 C6 C5 -1.3(11) . . . . ?
N1 C1 C6 F3 -7.6(11) . . . . ?
C2 C1 C6 F3 175.7(6) . . . . ?
C16 O5 C13 C14 165.0(8) 3_666 . . . ?
O5 C13 C14 O6 -88.4(10) . . . . ?
C15 O6 C14 C13 101.8(11) . . . . ?
C14 O6 C15 C16 -150.3(8) . . . . ?
O6 C15 C16 O5 74.6(12) . . . 3_666 ?
C20 O7 C17 C18 141.4(8) 3_576 . . . ?
C19 O8 C18 C17 108.7(10) . . . . ?
O7 C17 C18 O8 -80.5(11) . . . . ?
C18 O8 C19 C20 -173.5(7) . . . . ?
O8 C19 C20 O7 70.7(11) . . . 3_576 ?
O3 N4 C7 C12 -179.7(8) . . . . ?
O4 N4 C7 C12 -4.9(12) . . . . ?
O3 N4 C7 C8 -1.4(12) . . . . ?
O4 N4 C7 C8 173.4(8) . . . . ?
C12 C7 C8 N5 176.9(8) . . . . ?
N4 C7 C8 N5 -1.4(11) . . . . ?
C12 C7 C8 C9 1.4(10) . . . . ?
N4 C7 C8 C9 -176.9(7) . . . . ?
N5 C8 C9 F4 3.2(10) . . . . ?
C7 C8 C9 F4 179.0(6) . . . . ?
N5 C8 C9 C10 -176.7(7) . . . . ?
C7 C8 C9 C10 -1.0(11) . . . . ?
F4 C9 C10 N6 2.5(11) . . . . ?
C8 C9 C10 N6 -177.6(7) . . . . ?
F4 C9 C10 C11 179.2(6) . . . . ?
C8 C9 C10 C11 -0.9(11) . . . . ?
N6 C10 C11 F5 -1.1(11) . . . . ?
C9 C10 C11 F5 -178.0(7) . . . . ?
N6 C10 C11 C12 179.1(8) . . . . ?
C9 C10 C11 C12 2.3(11) . . . . ?
F5 C11 C12 F6 2.5(12) . . . . ?
C10 C11 C12 F6 -177.8(7) . . . . ?
F5 C11 C12 C7 178.4(7) . . . . ?
C10 C11 C12 C7 -1.9(13) . . . . ?
C8 C7 C12 C11 -0.1(12) . . . . ?
N4 C7 C12 C11 178.2(7) . . . . ?
C8 C7 C12 F6 175.6(7) . . . . ?
N4 C7 C12 F6 -6.1(12) . . . . ?
