#------------------------------------------------------------------------------
#$Date: 2024-09-06 03:20:09 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294531 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/90/7249097.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_7249097
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), C10 H20 O5'
_chemical_formula_sum            'C22 H28 F6 N6 O9'
_chemical_formula_weight         634.50
_chemical_melting_point          362
_chemical_name_systematic
;
Co-crystal of 2,4-diaminotrifluoronitrobenzene and 15-crown-5, 2:1
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                106.975(5)
_cell_angle_beta                 108.550(4)
_cell_angle_gamma                90.001(5)
_cell_formula_units_Z            2
_cell_length_a                   11.5203(14)
_cell_length_b                   11.5359(15)
_cell_length_c                   11.8617(17)
_cell_measurement_reflns_used    4613
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.60
_cell_volume                     1421.9(3)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_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  0.0472
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14729
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.593
_diffrn_reflns_theta_min         2.597
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5290
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0635
_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)+(0.0899P)²+1.2101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1710
_refine_ls_wR_factor_ref         0.2010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3401
_reflns_number_total             5290
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00612g2.cif
_cod_data_source_block           t701_1_2C15cr5
_cod_depositor_comments
'Adding full bibliography for 7249096--7249100.cif.'
_cod_database_code               7249097
_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   0.913
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 1.15281(16) 0.18351(19) 0.53490(18) 0.0563(5) Uani 1 1 d . . . . .
N1 N 0.7503(3) 0.0893(2) 0.5451(3) 0.0551(8) Uani 1 1 d . . . . .
C1 C 0.8297(3) 0.1183(3) 0.4846(3) 0.0398(7) Uani 1 1 d . . . . .
O1 O 0.6396(3) 0.0647(3) 0.4883(3) 0.0948(10) Uani 1 1 d . . . . .
N2 N 1.0171(3) 0.1389(2) 0.6634(2) 0.0522(7) Uani 1 1 d . . . . .
H2A H 1.095960 0.152972 0.694879 0.063 Uiso 1 1 calc R U . . .
H2B H 0.975414 0.123822 0.707076 0.063 Uiso 1 1 calc R U . . .
F2 F 0.80688(18) 0.1573(2) 0.18453(19) 0.0672(6) Uani 1 1 d . . . . .
O2 O 0.7936(3) 0.0881(3) 0.6543(3) 0.0722(8) Uani 1 1 d . . . . .
C2 C 0.9589(3) 0.1403(2) 0.5457(3) 0.0365(7) Uani 1 1 d . . . . .
N3 N 1.0582(2) 0.1878(3) 0.2938(3) 0.0501(7) Uani 1 1 d . . . . .
H3A H 1.136761 0.197881 0.329197 0.060 Uiso 1 1 calc R U . . .
H3B H 1.026481 0.189678 0.218231 0.060 Uiso 1 1 calc R U . . .
F3 F 0.66052(17) 0.1105(2) 0.3005(2) 0.0787(7) Uani 1 1 d . . . . .
C3 C 1.0282(3) 0.1648(3) 0.4770(3) 0.0374(7) Uani 1 1 d . . . . .
C4 C 0.9846(3) 0.1690(2) 0.3566(3) 0.0357(6) Uani 1 1 d . . . . .
C5 C 0.8562(3) 0.1502(3) 0.3019(3) 0.0423(7) Uani 1 1 d . . . . .
C6 C 0.7814(3) 0.1255(3) 0.3621(3) 0.0458(8) Uani 1 1 d . . . . .
O3 O 0.3276(3) 0.1657(3) 0.7753(3) 0.0778(8) Uani 1 1 d . . . . .
F4 F 0.71781(18) 0.33226(17) 0.7494(2) 0.0666(6) Uani 1 1 d . . . . .
N4 N 0.3318(3) 0.2769(3) 0.8139(3) 0.0553(7) Uani 1 1 d . . . . .
O4 O 0.2503(3) 0.3240(3) 0.8513(3) 0.0889(10) Uani 1 1 d . . . . .
N5 N 0.5392(3) 0.1790(3) 0.7364(4) 0.0726(10) Uani 1 1 d . . . . .
H5A H 0.601964 0.154008 0.715530 0.087 Uiso 1 1 calc R U . . .
H5B H 0.482635 0.127256 0.731384 0.087 Uiso 1 1 calc R U . . .
F5 F 0.52190(19) 0.67444(17) 0.8895(2) 0.0656(6) Uani 1 1 d . . . . .
N6 N 0.7181(3) 0.5795(2) 0.8258(3) 0.0539(7) Uani 1 1 d . . . . .
H6A H 0.778835 0.549079 0.804287 0.065 Uiso 1 1 calc R U . . .
H6B H 0.716488 0.657230 0.849950 0.065 Uiso 1 1 calc R U . . .
F6 F 0.33878(18) 0.5342(2) 0.8840(2) 0.0690(6) Uani 1 1 d . . . . .
C7 C 0.4300(3) 0.3515(3) 0.8138(3) 0.0417(7) Uani 1 1 d . . . . .
C8 C 0.5295(3) 0.2997(3) 0.7771(3) 0.0434(7) Uani 1 1 d . . . . .
C9 C 0.6218(3) 0.3808(3) 0.7843(3) 0.0427(7) Uani 1 1 d . . . . .
C10 C 0.6259(3) 0.5058(3) 0.8218(3) 0.0377(7) Uani 1 1 d . . . . .
C11 C 0.5242(3) 0.5520(3) 0.8541(3) 0.0404(7) Uani 1 1 d . . . . .
C12 C 0.4311(3) 0.4790(3) 0.8512(3) 0.0431(7) Uani 1 1 d . . . . .
O5 O 0.7226(2) 0.8312(2) 0.8269(2) 0.0596(6) Uani 1 1 d . . . A 1
O6 O 0.9639(2) 0.8033(2) 0.9584(2) 0.0638(7) Uani 1 1 d . . . A 1
O7 O 0.9755(3) 0.5625(3) 0.8247(3) 0.1004(11) Uani 1 1 d . . . A 1
O8 O 0.8214(7) 0.5018(9) 0.6055(6) 0.094(3) Uani 0.502(13) 1 d D . P A 1
O9 O 0.6826(2) 0.6999(3) 0.5788(3) 0.0694(7) Uani 1 1 d . . . A 1
C13 C 0.7989(4) 0.9269(3) 0.9257(4) 0.0660(11) Uani 1 1 d . . . A 1
H13A H 0.749796 0.980631 0.966664 0.079 Uiso 1 1 calc R U . A 1
H13B H 0.844036 0.973733 0.894318 0.079 Uiso 1 1 calc R U . A 1
C14 C 0.8871(4) 0.8743(3) 1.0169(3) 0.0602(9) Uani 1 1 d . . . A 1
H14A H 0.936739 0.939501 1.089280 0.072 Uiso 1 1 calc R U . A 1
H14B H 0.841788 0.824045 1.044809 0.072 Uiso 1 1 calc R U . A 1
C15 C 1.0203(4) 0.7196(4) 1.0176(4) 0.0741(12) Uani 1 1 d . . . A 1
H15A H 0.960545 0.678199 1.038544 0.089 Uiso 1 1 calc R U . A 1
H15B H 1.085808 0.761856 1.094423 0.089 Uiso 1 1 calc R U . A 1
C16 C 1.0722(4) 0.6279(4) 0.9316(4) 0.0727(11) Uani 1 1 d . . . A 1
H16A H 1.129675 0.669405 0.908116 0.087 Uiso 1 1 calc R U . A 1
H16B H 1.115947 0.572491 0.973925 0.087 Uiso 1 1 calc R U . A 1
C17 C 1.0106(5) 0.4908(5) 0.7287(6) 0.1073(19) Uani 0.5 1 d . . P A 1
H17A H 1.036771 0.416538 0.747150 0.129 Uiso 1 1 calc R U . A 1
H17B H 1.080747 0.533526 0.724227 0.129 Uiso 1 1 calc R U . A 1
C18 C 0.9161(7) 0.4597(5) 0.6105(6) 0.1028(18) Uani 0.502(13) 1 d D . P A 1
H18A H 0.947968 0.483705 0.553280 0.123 Uiso 0.502(13) 1 calc R U P A 1
H18B H 0.898984 0.371637 0.579742 0.123 Uiso 0.502(13) 1 calc R U P A 1
C19 C 0.7549(6) 0.5227(6) 0.4779(6) 0.130(3) Uani 0.502(13) 1 d D . P A 1
H19A H 0.805810 0.576188 0.458925 0.156 Uiso 0.502(13) 1 calc R U P A 1
H19B H 0.730205 0.446434 0.410251 0.156 Uiso 0.502(13) 1 calc R U P A 1
C20 C 0.6523(4) 0.5782(4) 0.5012(4) 0.0827(13) Uani 0.5 1 d . . P A 1
H20A H 0.616168 0.531890 0.540329 0.099 Uiso 1 1 calc R U . A 1
H20B H 0.590925 0.575750 0.422249 0.099 Uiso 1 1 calc R U . A 1
C21 C 0.5879(3) 0.7533(4) 0.6182(4) 0.0700(11) Uani 1 1 d . . . A 1
H21A H 0.546527 0.696564 0.642740 0.084 Uiso 1 1 calc R U . A 1
H21B H 0.528044 0.774414 0.550507 0.084 Uiso 1 1 calc R U . A 1
C22 C 0.6423(3) 0.8660(3) 0.7272(4) 0.0632(10) Uani 1 1 d . . . A 1
H22A H 0.687117 0.921024 0.703858 0.076 Uiso 1 1 calc R U . A 1
H22B H 0.577316 0.907709 0.752581 0.076 Uiso 1 1 calc R U . A 1
O8A O 0.8690(6) 0.5507(5) 0.5549(6) 0.067(3) Uani 0.498(13) 1 d D . P A 2
C17A C 1.0106(5) 0.4908(5) 0.7287(6) 0.1073(19) Uani 0.5 1 d . . P A 2
C18A C 0.9161(7) 0.4597(5) 0.6105(6) 0.1028(18) Uani 0.498(13) 1 d D . P A 2
H18C H 0.946095 0.400903 0.551818 0.123 Uiso 0.498(13) 1 calc R U P A 2
H18D H 0.847115 0.417618 0.617662 0.123 Uiso 0.498(13) 1 calc R U P A 2
C19A C 0.7549(6) 0.5227(6) 0.4779(6) 0.130(3) Uani 0.498(13) 1 d D . P A 2
H19C H 0.736329 0.436087 0.461342 0.156 Uiso 0.498(13) 1 calc R U P A 2
H19D H 0.755832 0.532940 0.399868 0.156 Uiso 0.498(13) 1 calc R U P A 2
C20A C 0.6523(4) 0.5782(4) 0.5012(4) 0.0827(13) Uani 0.5 1 d . . P A 2
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 120.5(3) . . ?
O1 N1 C1 119.9(3) . . ?
O2 N1 C1 119.7(3) . . ?
C6 C1 C2 118.5(3) . . ?
C6 C1 N1 120.5(3) . . ?
C2 C1 N1 121.0(3) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C2 C3 119.0(3) . . ?
N2 C2 C1 124.8(3) . . ?
C3 C2 C1 116.3(3) . . ?
C4 N3 H3A 120.0 . . ?
C4 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
F1 C3 C4 117.0(2) . . ?
F1 C3 C2 116.3(3) . . ?
C4 C3 C2 126.7(3) . . ?
N3 C4 C3 123.3(3) . . ?
N3 C4 C5 122.0(3) . . ?
C3 C4 C5 114.7(3) . . ?
F2 C5 C6 119.8(3) . . ?
F2 C5 C4 117.6(3) . . ?
C6 C5 C4 122.5(3) . . ?
F3 C6 C5 116.9(3) . . ?
F3 C6 C1 121.9(3) . . ?
C5 C6 C1 121.2(3) . . ?
O4 N4 O3 119.9(3) . . ?
O4 N4 C7 119.9(3) . . ?
O3 N4 C7 120.3(3) . . ?
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 N4 120.3(3) . . ?
C12 C7 C8 118.4(3) . . ?
N4 C7 C8 121.2(3) . . ?
N5 C8 C9 118.8(3) . . ?
N5 C8 C7 124.9(3) . . ?
C9 C8 C7 116.3(3) . . ?
F4 C9 C10 116.7(3) . . ?
F4 C9 C8 116.9(3) . . ?
C10 C9 C8 126.4(3) . . ?
N6 C10 C9 123.4(3) . . ?
N6 C10 C11 121.6(3) . . ?
C9 C10 C11 114.9(3) . . ?
C12 C11 F5 120.0(3) . . ?
C12 C11 C10 122.3(3) . . ?
F5 C11 C10 117.7(3) . . ?
F6 C12 C11 116.7(3) . . ?
F6 C12 C7 121.7(3) . . ?
C11 C12 C7 121.6(3) . . ?
C13 O5 C22 115.1(3) . . ?
C15 O6 C14 113.8(3) . . ?
C17 O7 C16 115.2(4) . . ?
C18 O8 C19 113.0(7) . . ?
C21 O9 C20 114.8(3) . . ?
O5 C13 C14 108.6(3) . . ?
O5 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
O5 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
O6 C14 C13 109.3(3) . . ?
O6 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O6 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
O6 C15 C16 109.4(3) . . ?
O6 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O6 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
O7 C16 C15 109.0(3) . . ?
O7 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
O7 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O7 C17 C18 113.6(4) . . ?
O7 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
O7 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
O8 C18 C17 117.7(5) . . ?
O8 C18 H18A 107.9 . . ?
C17 C18 H18A 107.9 . . ?
O8 C18 H18B 107.9 . . ?
C17 C18 H18B 107.9 . . ?
H18A C18 H18B 107.2 . . ?
C20 C19 O8 100.6(5) . . ?
C20 C19 H19A 111.7 . . ?
O8 C19 H19A 111.7 . . ?
C20 C19 H19B 111.7 . . ?
O8 C19 H19B 111.7 . . ?
H19A C19 H19B 109.4 . . ?
C19 C20 O9 112.8(4) . . ?
C19 C20 H20A 109.0 . . ?
O9 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
O9 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
O9 C21 C22 108.6(3) . . ?
O9 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
O9 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
O5 C22 C21 108.5(3) . . ?
O5 C22 H22A 110.0 . . ?
C21 C22 H22A 110.0 . . ?
O5 C22 H22B 110.0 . . ?
C21 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C19A O8A C18A 114.1(6) . . ?
O8A C18A C17A 120.7(5) . . ?
O8A C18A H18C 107.1 . . ?
C17A C18A H18C 107.1 . . ?
O8A C18A H18D 107.1 . . ?
C17A C18A H18D 107.1 . . ?
H18C C18A H18D 106.8 . . ?
O8A C19A C20A 125.0(5) . . ?
O8A C19A H19C 106.1 . . ?
C20A C19A H19C 106.1 . . ?
O8A C19A H19D 106.1 . . ?
C20A C19A H19D 106.1 . . ?
H19C C19A H19D 106.3 . . ?
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 1.365(3) . ?
N1 O1 1.225(4) . ?
N1 O2 1.235(4) . ?
N1 C1 1.422(4) . ?
C1 C6 1.409(5) . ?
C1 C2 1.418(4) . ?
N2 C2 1.348(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
F2 C5 1.353(4) . ?
C2 C3 1.390(4) . ?
N3 C4 1.348(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
F3 C6 1.335(3) . ?
C3 C4 1.371(4) . ?
C4 C5 1.402(4) . ?
C5 C6 1.357(4) . ?
O3 N4 1.226(4) . ?
F4 C9 1.366(3) . ?
N4 O4 1.223(4) . ?
N4 C7 1.422(4) . ?
N5 C8 1.351(4) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
F5 C11 1.354(3) . ?
N6 C10 1.341(4) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
F6 C12 1.344(3) . ?
C7 C12 1.406(4) . ?
C7 C8 1.424(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.375(4) . ?
C10 C11 1.403(4) . ?
C11 C12 1.349(4) . ?
O5 C13 1.398(4) . ?
O5 C22 1.413(4) . ?
O6 C15 1.397(5) . ?
O6 C14 1.411(4) . ?
O7 C17 1.373(6) . ?
O7 C16 1.400(5) . ?
O8 C18 1.186(7) . ?
O8 C19 1.553(9) . ?
O9 C21 1.394(5) . ?
O9 C20 1.408(5) . ?
C13 C14 1.501(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.509(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.419(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.410(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.502(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
O8A C19A 1.315(7) . ?
O8A C18A 1.417(8) . ?
C17A C18A 1.419(8) . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C19A C20A 1.410(7) . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
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 3.5(5) . . . . ?
O2 N1 C1 C6 -177.1(3) . . . . ?
O1 N1 C1 C2 -176.4(3) . . . . ?
O2 N1 C1 C2 3.0(4) . . . . ?
C6 C1 C2 N2 178.6(3) . . . . ?
N1 C1 C2 N2 -1.6(4) . . . . ?
C6 C1 C2 C3 -1.4(4) . . . . ?
N1 C1 C2 C3 178.4(3) . . . . ?
N2 C2 C3 F1 1.3(4) . . . . ?
C1 C2 C3 F1 -178.7(2) . . . . ?
N2 C2 C3 C4 179.5(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
F1 C3 C4 N3 1.5(4) . . . . ?
C2 C3 C4 N3 -176.8(3) . . . . ?
F1 C3 C4 C5 -179.5(2) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
N3 C4 C5 F2 -3.1(4) . . . . ?
C3 C4 C5 F2 177.8(3) . . . . ?
N3 C4 C5 C6 176.9(3) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
F2 C5 C6 F3 -0.6(4) . . . . ?
C4 C5 C6 F3 179.4(3) . . . . ?
F2 C5 C6 C1 -179.6(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C2 C1 C6 F3 -177.4(3) . . . . ?
N1 C1 C6 F3 2.7(5) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
N1 C1 C6 C5 -178.4(3) . . . . ?
O4 N4 C7 C12 -2.9(5) . . . . ?
O3 N4 C7 C12 176.3(3) . . . . ?
O4 N4 C7 C8 176.6(3) . . . . ?
O3 N4 C7 C8 -4.2(5) . . . . ?
C12 C7 C8 N5 -178.4(3) . . . . ?
N4 C7 C8 N5 2.1(5) . . . . ?
C12 C7 C8 C9 1.4(4) . . . . ?
N4 C7 C8 C9 -178.1(3) . . . . ?
N5 C8 C9 F4 -0.2(5) . . . . ?
C7 C8 C9 F4 -180.0(3) . . . . ?
N5 C8 C9 C10 179.0(3) . . . . ?
C7 C8 C9 C10 -0.8(5) . . . . ?
F4 C9 C10 N6 -0.4(5) . . . . ?
C8 C9 C10 N6 -179.5(3) . . . . ?
F4 C9 C10 C11 178.6(3) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
N6 C10 C11 C12 -179.6(3) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
N6 C10 C11 F5 0.2(4) . . . . ?
C9 C10 C11 F5 -178.8(3) . . . . ?
F5 C11 C12 F6 0.3(4) . . . . ?
C10 C11 C12 F6 -179.9(3) . . . . ?
F5 C11 C12 C7 179.4(3) . . . . ?
C10 C11 C12 C7 -0.8(5) . . . . ?
N4 C7 C12 F6 -2.2(5) . . . . ?
C8 C7 C12 F6 178.3(3) . . . . ?
N4 C7 C12 C11 178.8(3) . . . . ?
C8 C7 C12 C11 -0.7(5) . . . . ?
C22 O5 C13 C14 -174.1(3) . . . . ?
C15 O6 C14 C13 -160.1(3) . . . . ?
O5 C13 C14 O6 63.8(4) . . . . ?
C14 O6 C15 C16 165.4(3) . . . . ?
C17 O7 C16 C15 169.1(4) . . . . ?
O6 C15 C16 O7 -63.1(5) . . . . ?
C16 O7 C17 C18 -159.7(5) . . . . ?
C19 O8 C18 C17 149.2(6) . . . . ?
O7 C17 C18 O8 3.4(10) . . . . ?
C18 O8 C19 C20 -176.8(8) . . . . ?
O8 C19 C20 O9 74.5(6) . . . . ?
C21 O9 C20 C19 -171.7(5) . . . . ?
C20 O9 C21 C22 163.5(3) . . . . ?
C13 O5 C22 C21 167.6(3) . . . . ?
O9 C21 C22 O5 -63.5(4) . . . . ?
C19A O8A C18A C17A -153.2(6) . . . . ?
C18A O8A C19A C20A 109.6(8) . . . . ?
