#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:06:39 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246683.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_7246683
loop_
_publ_author_name
'Vaganova, Tamara A.'
'Gatilov, Yurij V.'
'Kryuchkova, Natalia A.'
'Pishchur, Denis P.'
'Zhukovets, Anastasia A.'
'Malykhin, Evgenij V.'
_publ_section_title
;
 How does the combination of the nitro group and fluorine atoms affect the
 (co)crystallization behaviour of arylenediamines?
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3284
_journal_page_last               3298
_journal_paper_doi               10.1039/D3CE00327B
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '2(C6 H4 F3 N3 O2), C12 H24 O6'
_chemical_formula_sum            'C24 H32 F6 N6 O10'
_chemical_formula_weight         678.55
_chemical_melting_point          424.7
_chemical_name_systematic
;
2,4,5-trifluoro-6-nitrobenzene-1,3-diamine 18-crown-6 2:1 cocrystal
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-04 deposited with the CCDC.	2023-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                73.313(2)
_cell_angle_beta                 77.9280(10)
_cell_angle_gamma                80.0470(10)
_cell_formula_units_Z            2
_cell_length_a                   11.6265(4)
_cell_length_b                   11.6941(6)
_cell_length_c                   12.1146(6)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.31
_cell_volume                     1531.64(12)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41112
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.174
_diffrn_reflns_theta_min         2.197
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_correction_T_min  0.8997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         6787
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0437
_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)+(0.0741P)²+0.6005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1448
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4918
_reflns_number_total             6787
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00327b2.cif
_cod_data_source_block           2Acr-a3_3mal
_cod_depositor_comments
'Adding full bibliography for 7246683--7246691.cif.'
_cod_database_code               7246683
_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   0.920
_shelx_estimated_absorpt_t_max   0.986
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 0.26882(10) 0.65635(13) 0.01787(11) 0.0588(3) Uani 1 1 d . . . . .
O1 O -0.22216(13) 0.64599(18) -0.03070(15) 0.0699(5) Uani 1 1 d . . . . .
N1 N 0.14132(16) 0.64496(17) -0.13456(14) 0.0500(4) Uani 1 1 d D . . . .
H1B H 0.2185(15) 0.654(2) -0.152(2) 0.064(7) Uiso 1 1 d D . . . .
H1A H 0.0955(19) 0.646(2) -0.1840(19) 0.058(7) Uiso 1 1 d D . . . .
C1 C -0.03983(14) 0.64626(14) 0.01254(14) 0.0317(3) Uani 1 1 d . . . . .
O2 O -0.07228(14) 0.63737(14) -0.16551(12) 0.0567(4) Uani 1 1 d . . . . .
N2 N 0.17409(15) 0.67037(17) 0.24200(15) 0.0482(4) Uani 1 1 d D . . . .
H2A H 0.2480(15) 0.685(2) 0.214(2) 0.057(6) Uiso 1 1 d D . . . .
H2B H 0.1386(19) 0.686(2) 0.3091(16) 0.055(6) Uiso 1 1 d D . . . .
F2 F -0.06448(10) 0.66077(11) 0.31317(9) 0.0524(3) Uani 1 1 d . . . . .
C2 C 0.08416(15) 0.64851(14) -0.02594(14) 0.0332(3) Uani 1 1 d . . . . .
F3 F -0.20211(9) 0.64656(13) 0.17283(11) 0.0571(3) Uani 1 1 d . . . . .
C3 C 0.15041(15) 0.65579(16) 0.05436(15) 0.0365(4) Uani 1 1 d . . . . .
N3 N -0.11500(14) 0.64294(13) -0.06436(13) 0.0396(3) Uani 1 1 d . . . . .
C4 C 0.10618(15) 0.66274(15) 0.16757(15) 0.0345(4) Uani 1 1 d . . . . .
C5 C -0.01657(15) 0.65783(15) 0.20224(14) 0.0345(4) Uani 1 1 d . . . . .
C6 C -0.08680(14) 0.65016(14) 0.12914(15) 0.0332(3) Uani 1 1 d . . . . .
O5 O 0.11218(13) 0.97143(12) 0.11082(13) 0.0549(4) Uani 1 1 d . . . . .
O6 O 0.35773(14) 0.90279(15) 0.06062(13) 0.0590(4) Uani 1 1 d . . . . .
O7 O 0.44235(12) 0.67284(14) 0.19613(13) 0.0543(4) Uani 1 1 d . . . . .
O8 O 0.33463(13) 0.59011(12) 0.43419(12) 0.0493(3) Uani 1 1 d . . . . .
O9 O 0.09564(12) 0.69590(12) 0.49393(11) 0.0472(3) Uani 1 1 d . . . . .
O10 O 0.01483(12) 0.91997(13) 0.35178(13) 0.0525(4) Uani 1 1 d . . . . .
C13 C 0.1886(2) 1.04036(19) 0.01860(19) 0.0581(6) Uani 1 1 d . . . . .
H13A H 0.219128 1.096847 0.046806 0.070 Uiso 1 1 calc R U . . .
H13B H 0.145113 1.085701 -0.043570 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2881(2) 0.9590(2) -0.02684(18) 0.0601(6) Uani 1 1 d . . . . .
H14A H 0.257353 0.898694 -0.049533 0.072 Uiso 1 1 calc R U . . .
H14B H 0.336221 1.004723 -0.095288 0.072 Uiso 1 1 calc R U . . .
C15 C 0.45986(19) 0.8311(2) 0.0208(2) 0.0592(6) Uani 1 1 d . . . . .
H15A H 0.514897 0.882081 -0.034882 0.071 Uiso 1 1 calc R U . . .
H15B H 0.438077 0.778316 -0.018260 0.071 Uiso 1 1 calc R U . . .
C16 C 0.51697(18) 0.7586(2) 0.1210(2) 0.0605(6) Uani 1 1 d . . . . .
H16A H 0.592303 0.717337 0.092775 0.073 Uiso 1 1 calc R U . . .
H16B H 0.532038 0.811043 0.164280 0.073 Uiso 1 1 calc R U . . .
C17 C 0.50088(19) 0.5879(2) 0.2834(2) 0.0573(5) Uani 1 1 d . . . . .
H17A H 0.538450 0.629695 0.322137 0.069 Uiso 1 1 calc R U . . .
H17B H 0.561836 0.535585 0.247405 0.069 Uiso 1 1 calc R U . . .
C18 C 0.4130(2) 0.51490(19) 0.3707(2) 0.0586(6) Uani 1 1 d . . . . .
H18A H 0.368702 0.480643 0.331088 0.070 Uiso 1 1 calc R U . . .
H18B H 0.453613 0.449538 0.423785 0.070 Uiso 1 1 calc R U . . .
C19 C 0.2448(2) 0.52854(18) 0.51650(18) 0.0530(5) Uani 1 1 d . . . . .
H19A H 0.280203 0.463642 0.574115 0.064 Uiso 1 1 calc R U . . .
H19B H 0.200309 0.494271 0.477062 0.064 Uiso 1 1 calc R U . . .
C20 C 0.1642(2) 0.61552(19) 0.57516(17) 0.0520(5) Uani 1 1 d . . . . .
H20A H 0.112296 0.572561 0.642174 0.062 Uiso 1 1 calc R U . . .
H20B H 0.210287 0.660269 0.602431 0.062 Uiso 1 1 calc R U . . .
C21 C 0.0252(2) 0.7892(2) 0.54057(18) 0.0568(5) Uani 1 1 d . . . . .
H21A H 0.075954 0.840766 0.552434 0.068 Uiso 1 1 calc R U . . .
H21B H -0.021475 0.754599 0.615480 0.068 Uiso 1 1 calc R U . . .
C22 C -0.05424(19) 0.8605(2) 0.4575(2) 0.0573(5) Uani 1 1 d . . . . .
H22A H -0.101040 0.807860 0.441541 0.069 Uiso 1 1 calc R U . . .
H22B H -0.108005 0.919298 0.491657 0.069 Uiso 1 1 calc R U . . .
C23 C -0.05412(18) 0.97096(19) 0.2618(2) 0.0544(5) Uani 1 1 d . . . . .
H23A H -0.123728 1.020426 0.289796 0.065 Uiso 1 1 calc R U . . .
H23B H -0.080240 0.907475 0.239699 0.065 Uiso 1 1 calc R U . . .
C24 C 0.01748(18) 1.04516(18) 0.1590(2) 0.0518(5) Uani 1 1 d . . . . .
H24A H -0.031929 1.086745 0.100703 0.062 Uiso 1 1 calc R U . . .
H24B H 0.048259 1.105032 0.182334 0.062 Uiso 1 1 calc R U . . .
O3 O 0.69672(15) 1.16064(17) 0.3460(2) 0.0819(6) Uani 1 1 d . . . . .
O4 O 0.59016(15) 1.30193(14) 0.24214(17) 0.0681(5) Uani 1 1 d . . . . .
F4 F 0.22796(10) 1.11159(11) 0.26480(12) 0.0556(3) Uani 1 1 d . . . . .
N4 N 0.37433(16) 1.27401(15) 0.23007(17) 0.0540(4) Uani 1 1 d . . . . .
H4B H 0.304743 1.293423 0.211542 0.065 Uiso 1 1 calc R U . . .
H4A H 0.419982 1.328539 0.217688 0.065 Uiso 1 1 calc R U . . .
N5 N 0.28363(15) 0.87078(15) 0.36028(16) 0.0499(4) Uani 1 1 d . . . . .
H5A H 0.215387 0.895409 0.339400 0.060 Uiso 1 1 calc R U . . .
H5B H 0.302785 0.795536 0.390613 0.060 Uiso 1 1 calc R U . . .
F5 F 0.50095(11) 0.79505(10) 0.42958(12) 0.0596(3) Uani 1 1 d . . . . .
F6 F 0.65509(10) 0.94577(11) 0.39965(13) 0.0622(3) Uani 1 1 d . . . . .
N6 N 0.60786(14) 1.19584(15) 0.30024(15) 0.0458(4) Uani 1 1 d . . . . .
C7 C 0.52400(15) 1.11575(16) 0.31453(15) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.41188(15) 1.15798(16) 0.27857(15) 0.0362(4) Uani 1 1 d . . . . .
C9 C 0.33600(15) 1.07162(16) 0.29759(15) 0.0373(4) Uani 1 1 d . . . . .
C10 C 0.36033(15) 0.94985(16) 0.34551(15) 0.0369(4) Uani 1 1 d . . . . .
C11 C 0.47243(16) 0.91313(16) 0.37996(16) 0.0391(4) Uani 1 1 d . . . . .
C12 C 0.55085(15) 0.99170(17) 0.36546(16) 0.0388(4) 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
C2 N1 H1B 117.7(16) . . ?
C2 N1 H1A 115.2(16) . . ?
H1B N1 H1A 126(2) . . ?
C6 C1 N3 120.71(15) . . ?
C6 C1 C2 118.25(15) . . ?
N3 C1 C2 121.03(15) . . ?
C4 N2 H2A 118.5(16) . . ?
C4 N2 H2B 118.5(15) . . ?
H2A N2 H2B 119(2) . . ?
N1 C2 C3 118.19(16) . . ?
N1 C2 C1 124.77(16) . . ?
C3 C2 C1 117.04(15) . . ?
F1 C3 C4 117.37(15) . . ?
F1 C3 C2 116.89(15) . . ?
C4 C3 C2 125.74(15) . . ?
O1 N3 O2 120.17(16) . . ?
O1 N3 C1 119.90(16) . . ?
O2 N3 C1 119.93(15) . . ?
N2 C4 C3 123.52(16) . . ?
N2 C4 C5 121.39(16) . . ?
C3 C4 C5 115.07(15) . . ?
F2 C5 C6 119.64(15) . . ?
F2 C5 C4 117.80(15) . . ?
C6 C5 C4 122.56(15) . . ?
F3 C6 C5 116.63(15) . . ?
F3 C6 C1 122.06(15) . . ?
C5 C6 C1 121.31(15) . . ?
C13 O5 C24 111.52(16) . . ?
C14 O6 C15 112.68(17) . . ?
C17 O7 C16 112.35(16) . . ?
C18 O8 C19 112.62(16) . . ?
C20 O9 C21 111.92(15) . . ?
C23 O10 C22 111.78(16) . . ?
O5 C13 C14 109.38(17) . . ?
O5 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O5 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
O6 C14 C13 109.34(18) . . ?
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 109.69(18) . . ?
O6 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
O6 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O7 C16 C15 110.13(17) . . ?
O7 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
O7 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
O7 C17 C18 109.50(17) . . ?
O7 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
O7 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O8 C18 C17 108.90(17) . . ?
O8 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
O8 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O8 C19 C20 108.78(16) . . ?
O8 C19 H19A 109.9 . . ?
C20 C19 H19A 109.9 . . ?
O8 C19 H19B 109.9 . . ?
C20 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
O9 C20 C19 108.97(16) . . ?
O9 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
O9 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
O9 C21 C22 109.02(17) . . ?
O9 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
O9 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
O10 C22 C21 109.45(17) . . ?
O10 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
O10 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
O10 C23 C24 109.68(16) . . ?
O10 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
O10 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
O5 C24 C23 109.90(16) . . ?
O5 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
O5 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
C8 N4 H4B 120.0 . . ?
C8 N4 H4A 120.0 . . ?
H4B N4 H4A 120.0 . . ?
C10 N5 H5A 120.0 . . ?
C10 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O3 N6 O4 120.41(16) . . ?
O3 N6 C7 119.96(17) . . ?
O4 N6 C7 119.63(16) . . ?
C12 C7 C8 118.76(15) . . ?
C12 C7 N6 120.07(16) . . ?
C8 C7 N6 121.17(16) . . ?
N4 C8 C9 118.73(16) . . ?
N4 C8 C7 124.91(16) . . ?
C9 C8 C7 116.35(16) . . ?
F4 C9 C10 117.12(15) . . ?
F4 C9 C8 116.68(16) . . ?
C10 C9 C8 126.20(16) . . ?
N5 C10 C9 123.33(16) . . ?
N5 C10 C11 121.66(17) . . ?
C9 C10 C11 115.00(15) . . ?
F5 C11 C12 119.66(16) . . ?
F5 C11 C10 117.96(16) . . ?
C12 C11 C10 122.38(16) . . ?
F6 C12 C11 116.83(16) . . ?
F6 C12 C7 121.87(16) . . ?
C11 C12 C7 121.30(16) . . ?
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 1.356(2) . ?
O1 N3 1.225(2) . ?
N1 C2 1.353(2) . ?
N1 H1B 0.896(16) . ?
N1 H1A 0.878(16) . ?
C1 C6 1.415(2) . ?
C1 N3 1.416(2) . ?
C1 C2 1.422(2) . ?
O2 N3 1.238(2) . ?
N2 C4 1.346(2) . ?
N2 H2A 0.883(16) . ?
N2 H2B 0.887(16) . ?
F2 C5 1.3507(19) . ?
C2 C3 1.389(2) . ?
F3 C6 1.3376(19) . ?
C3 C4 1.381(2) . ?
C4 C5 1.407(2) . ?
C5 C6 1.354(2) . ?
O5 C13 1.415(3) . ?
O5 C24 1.410(3) . ?
O6 C14 1.409(3) . ?
O6 C15 1.412(3) . ?
O7 C17 1.426(3) . ?
O7 C16 1.426(3) . ?
O8 C18 1.419(3) . ?
O8 C19 1.420(3) . ?
O9 C20 1.423(2) . ?
O9 C21 1.425(2) . ?
O10 C23 1.419(3) . ?
O10 C22 1.422(3) . ?
C13 C14 1.483(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.478(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.490(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.492(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.484(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.481(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O3 N6 1.227(2) . ?
O4 N6 1.244(2) . ?
F4 C9 1.3613(19) . ?
N4 C8 1.350(2) . ?
N4 H4B 0.8600 . ?
N4 H4A 0.8600 . ?
N5 C10 1.344(2) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
F5 C11 1.351(2) . ?
F6 C12 1.337(2) . ?
N6 C7 1.418(2) . ?
C7 C12 1.412(3) . ?
C7 C8 1.423(2) . ?
C8 C9 1.393(2) . ?
C9 C10 1.378(3) . ?
C10 C11 1.410(2) . ?
C11 C12 1.355(3) . ?
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
C6 C1 C2 N1 179.79(16) . . . . ?
N3 C1 C2 N1 -1.6(3) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
N3 C1 C2 C3 177.90(15) . . . . ?
N1 C2 C3 F1 -1.3(2) . . . . ?
C1 C2 C3 F1 179.17(15) . . . . ?
N1 C2 C3 C4 178.56(17) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C6 C1 N3 O1 1.5(2) . . . . ?
C2 C1 N3 O1 -177.03(17) . . . . ?
C6 C1 N3 O2 -178.70(15) . . . . ?
C2 C1 N3 O2 2.7(2) . . . . ?
F1 C3 C4 N2 0.3(3) . . . . ?
C2 C3 C4 N2 -179.59(17) . . . . ?
F1 C3 C4 C5 -178.00(15) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
N2 C4 C5 F2 -0.1(3) . . . . ?
C3 C4 C5 F2 178.16(15) . . . . ?
N2 C4 C5 C6 179.99(17) . . . . ?
C3 C4 C5 C6 -1.7(2) . . . . ?
F2 C5 C6 F3 0.4(2) . . . . ?
C4 C5 C6 F3 -179.77(15) . . . . ?
F2 C5 C6 C1 -179.68(15) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
N3 C1 C6 F3 2.4(2) . . . . ?
C2 C1 C6 F3 -178.97(15) . . . . ?
N3 C1 C6 C5 -177.53(15) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C24 O5 C13 C14 178.52(17) . . . . ?
C15 O6 C14 C13 -175.25(18) . . . . ?
O5 C13 C14 O6 -65.4(2) . . . . ?
C14 O6 C15 C16 -170.11(19) . . . . ?
C17 O7 C16 C15 170.38(18) . . . . ?
O6 C15 C16 O7 66.6(2) . . . . ?
C16 O7 C17 C18 170.23(18) . . . . ?
C19 O8 C18 C17 177.70(17) . . . . ?
O7 C17 C18 O8 -67.7(2) . . . . ?
C18 O8 C19 C20 -177.66(17) . . . . ?
C21 O9 C20 C19 -174.03(17) . . . . ?
O8 C19 C20 O9 71.1(2) . . . . ?
C20 O9 C21 C22 -173.23(17) . . . . ?
C23 O10 C22 C21 168.97(18) . . . . ?
O9 C21 C22 O10 -65.0(2) . . . . ?
C22 O10 C23 C24 172.53(18) . . . . ?
C13 O5 C24 C23 -174.88(17) . . . . ?
O10 C23 C24 O5 65.3(2) . . . . ?
O3 N6 C7 C12 -9.9(3) . . . . ?
O4 N6 C7 C12 170.83(18) . . . . ?
O3 N6 C7 C8 169.98(19) . . . . ?
O4 N6 C7 C8 -9.3(3) . . . . ?
C12 C7 C8 N4 179.21(17) . . . . ?
N6 C7 C8 N4 -0.6(3) . . . . ?
C12 C7 C8 C9 0.3(2) . . . . ?
N6 C7 C8 C9 -179.51(16) . . . . ?
N4 C8 C9 F4 0.2(3) . . . . ?
C7 C8 C9 F4 179.17(15) . . . . ?
N4 C8 C9 C10 179.71(18) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
F4 C9 C10 N5 0.3(3) . . . . ?
C8 C9 C10 N5 -179.15(18) . . . . ?
F4 C9 C10 C11 -178.93(15) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
N5 C10 C11 F5 -0.4(3) . . . . ?
C9 C10 C11 F5 178.82(16) . . . . ?
N5 C10 C11 C12 179.87(17) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
F5 C11 C12 F6 1.5(3) . . . . ?
C10 C11 C12 F6 -178.82(16) . . . . ?
F5 C11 C12 C7 -179.68(16) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C8 C7 C12 F6 179.04(16) . . . . ?
N6 C7 C12 F6 -1.1(3) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
N6 C7 C12 C11 -179.88(17) . . . . ?
