#------------------------------------------------------------------------------
#$Date: 2024-01-06 10:00:53 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247783.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_7247783
loop_
_publ_author_name
'Krawczyk, Marta S.'
'Krawczyk, Monika K.'
'Majerz, Irena'
_publ_section_title
;
 Polymorphism of amantadinium niflumate
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              6748
_journal_page_last               6757
_journal_paper_doi               10.1039/D3CE00754E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C13 H8 F3 N2 O2, C10 H18 N'
_chemical_formula_sum            'C23 H26 F3 N3 O2'
_chemical_formula_weight         433.47
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-07-03 deposited with the CCDC.	2023-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.29(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.953(6)
_cell_length_b                   6.359(3)
_cell_length_c                   20.573(6)
_cell_measurement_reflns_used    8748
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.24
_cell_measurement_theta_min      2.71
_cell_volume                     2105.8(14)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16441
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         73.031
_diffrn_reflns_theta_min         2.745
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.551
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4076
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0715P)²+0.8293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3577
_reflns_number_total             4076
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00754e2.cif
_cod_data_source_block           I_polymorph
_cod_depositor_comments
'Adding full bibliography for 7247782--7247783.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247783
_shelx_shelxl_version_number     2014/7
_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   0.763
_shelx_estimated_absorpt_t_max   0.965
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
O1 O 0.48389(6) 0.90878(16) 0.33036(5) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.54342(6) 0.61034(16) 0.37796(5) 0.0243(2) Uani 1 1 d . . . . .
C1 C 0.53225(8) 0.8071(2) 0.37960(7) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.58051(8) 0.9265(2) 0.44260(6) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.65670(8) 0.8526(2) 0.48937(7) 0.0193(3) Uani 1 1 d . . . . .
N4 N 0.69881(7) 0.9613(2) 0.54540(6) 0.0225(3) Uani 1 1 d . . . . .
C5 C 0.66739(9) 1.1459(2) 0.55689(7) 0.0236(3) Uani 1 1 d . . . . .
H5 H 0.6974 1.2226 0.5966 0.028 Uiso 1 1 calc R U . . .
C6 C 0.59438(9) 1.2324(2) 0.51493(7) 0.0229(3) Uani 1 1 d . . . . .
H6 H 0.5745 1.3638 0.5253 0.027 Uiso 1 1 calc R U . . .
C7 C 0.55125(8) 1.1190(2) 0.45690(7) 0.0202(3) Uani 1 1 d . . . . .
H7 H 0.5010 1.1741 0.4266 0.024 Uiso 1 1 calc R U . . .
N1 N 0.68866(7) 0.6638(2) 0.47676(6) 0.0222(3) Uani 1 1 d . . . . .
H1N H 0.6535(10) 0.590(3) 0.4439(9) 0.027 Uiso 1 1 d . U . . .
C8 C 0.76918(8) 0.5819(2) 0.50259(7) 0.0210(3) Uani 1 1 d . . . . .
C9 C 0.83619(8) 0.6871(2) 0.54798(7) 0.0246(3) Uani 1 1 d . . . . .
H9 H 0.8290 0.8226 0.5647 0.029 Uiso 1 1 calc R U . . .
C10 C 0.91378(9) 0.5901(3) 0.56833(8) 0.0296(4) Uani 1 1 d . . . . .
C11 C 0.92656(9) 0.3925(3) 0.54537(9) 0.0328(4) Uani 1 1 d . . . . .
H11 H 0.9800 0.3291 0.5602 0.039 Uiso 1 1 calc R U . . .
C12 C 0.85951(9) 0.2887(3) 0.50020(8) 0.0308(4) Uani 1 1 d . . . . .
H12 H 0.8669 0.1528 0.4838 0.037 Uiso 1 1 calc R U . . .
C13 C 0.78206(9) 0.3823(2) 0.47896(7) 0.0243(3) Uani 1 1 d . . . . .
H13 H 0.7368 0.3101 0.4478 0.029 Uiso 1 1 calc R U . . .
C14 C 0.9810(4) 0.7233(8) 0.6092(3) 0.042(2) Uani 0.5 1 d D . P A 1
F1 F 0.96833(19) 0.8076(6) 0.66287(17) 0.0505(9) Uani 0.5 1 d D . P A 1
F2 F 1.0498(4) 0.6192(11) 0.6344(4) 0.123(3) Uani 0.5 1 d D . P A 1
F3 F 1.0030(2) 0.8812(6) 0.5779(2) 0.0494(8) Uani 0.5 1 d D . P A 1
C141 C 0.9866(3) 0.6949(10) 0.6227(3) 0.038(2) Uani 0.5 1 d D . P A 2
F11 F 0.9815(3) 0.6774(14) 0.6843(2) 0.160(4) Uani 0.5 1 d D . P A 2
F21 F 1.0591(3) 0.6168(7) 0.6278(2) 0.0406(9) Uani 0.5 1 d D . P A 2
F31 F 0.9865(4) 0.8967(8) 0.6105(5) 0.220(6) Uani 0.5 1 d D . P A 2
N3 N 0.45311(7) 0.3220(2) 0.28212(6) 0.0189(3) Uani 1 1 d . . . . .
H3NA H 0.4730(10) 0.330(3) 0.2441(9) 0.028 Uiso 1 1 d . U . . .
H3NB H 0.4686(10) 0.184(3) 0.3047(9) 0.028 Uiso 1 1 d . U . . .
H3NC H 0.4807(10) 0.429(3) 0.3143(9) 0.028 Uiso 1 1 d . U . . .
C1A C 0.36004(8) 0.3541(2) 0.25976(7) 0.0187(3) Uani 1 1 d . . . . .
C2A C 0.31717(8) 0.1576(2) 0.22237(7) 0.0229(3) Uani 1 1 d . . . . .
H2A H 0.3327 0.0338 0.2529 0.028 Uiso 1 1 calc R U . . .
H2B H 0.3348 0.1316 0.1815 0.028 Uiso 1 1 calc R U . . .
C3A C 0.22244(9) 0.1918(3) 0.20057(8) 0.0282(3) Uani 1 1 d . . . . .
H3A H 0.1935 0.0644 0.1758 0.034 Uiso 1 1 calc R U . . .
C4A C 0.19593(9) 0.2293(3) 0.26446(9) 0.0294(3) Uani 1 1 d . . . . .
H4A H 0.1350 0.2491 0.2509 0.035 Uiso 1 1 calc R U . . .
H4B H 0.2106 0.1054 0.2950 0.035 Uiso 1 1 calc R U . . .
C5A C 0.23983(9) 0.4249(2) 0.30234(7) 0.0241(3) Uani 1 1 d . . . . .
H5A H 0.2224 0.4492 0.3439 0.029 Uiso 1 1 calc R U . . .
C6A C 0.33445(8) 0.3906(2) 0.32403(7) 0.0217(3) Uani 1 1 d . . . . .
H6A H 0.3635 0.5155 0.3491 0.026 Uiso 1 1 calc R U . . .
H6B H 0.3499 0.2672 0.3548 0.026 Uiso 1 1 calc R U . . .
C7A C 0.33763(8) 0.5462(2) 0.21311(7) 0.0211(3) Uani 1 1 d . . . . .
H7A H 0.3555 0.5244 0.1722 0.025 Uiso 1 1 calc R U . . .
H7B H 0.3664 0.6721 0.2377 0.025 Uiso 1 1 calc R U . . .
C8A C 0.24298(9) 0.5794(2) 0.19123(7) 0.0234(3) Uani 1 1 d . . . . .
H8A H 0.2276 0.7044 0.1603 0.028 Uiso 1 1 calc R U . . .
C9A C 0.19949(9) 0.3828(3) 0.15323(8) 0.0290(4) Uani 1 1 d . . . . .
H9A H 0.1385 0.4037 0.1382 0.035 Uiso 1 1 calc R U . . .
H9B H 0.2167 0.3588 0.1121 0.035 Uiso 1 1 calc R U . . .
C10A C 0.21666(9) 0.6163(2) 0.25511(7) 0.0236(3) Uani 1 1 d . . . . .
H10A H 0.2448 0.7430 0.2796 0.028 Uiso 1 1 calc R U . . .
H10B H 0.1559 0.6399 0.2415 0.028 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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 C1 O2 123.29(13) . . ?
O1 C1 C2 118.25(13) . . ?
O2 C1 C2 118.43(12) . . ?
C7 C2 C3 117.13(13) . . ?
C7 C2 C1 119.65(12) . . ?
C3 C2 C1 123.22(13) . . ?
N4 C3 N1 118.50(13) . . ?
N4 C3 C2 122.34(13) . . ?
N1 C3 C2 119.16(12) . . ?
C5 N4 C3 117.97(12) . . ?
N4 C5 C6 124.46(13) . . ?
N4 C5 H5 117.8 . . ?
C6 C5 H5 117.8 . . ?
C5 C6 C7 117.20(14) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C2 C7 C6 120.89(13) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C3 N1 C8 130.39(13) . . ?
C3 N1 H1N 113.4(11) . . ?
C8 N1 H1N 115.9(11) . . ?
C9 C8 C13 118.95(13) . . ?
C9 C8 N1 124.62(14) . . ?
C13 C8 N1 116.41(13) . . ?
C10 C9 C8 118.90(15) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C9 122.25(15) . . ?
C11 C10 C14 123.2(2) . . ?
C9 C10 C14 114.2(2) . . ?
C11 C10 C141 117.9(3) . . ?
C9 C10 C141 119.7(3) . . ?
C10 C11 C12 118.51(15) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 120.26(16) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 121.13(14) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
F2 C14 F1 103.7(6) . . ?
F2 C14 F3 103.2(5) . . ?
F1 C14 F3 104.5(4) . . ?
F2 C14 C10 112.1(5) . . ?
F1 C14 C10 114.9(4) . . ?
F3 C14 C10 117.0(5) . . ?
F21 C141 F11 103.8(5) . . ?
F21 C141 F31 109.5(5) . . ?
F11 C141 F31 105.9(5) . . ?
F21 C141 C10 114.7(4) . . ?
F11 C141 C10 112.9(4) . . ?
F31 C141 C10 109.5(5) . . ?
C1A N3 H3NA 110.5(10) . . ?
C1A N3 H3NB 111.1(10) . . ?
H3NA N3 H3NB 108.9(14) . . ?
C1A N3 H3NC 110.3(10) . . ?
H3NA N3 H3NC 108.0(15) . . ?
H3NB N3 H3NC 107.9(14) . . ?
N3 C1A C7A 109.21(11) . . ?
N3 C1A C2A 109.22(11) . . ?
C7A C1A C2A 110.68(12) . . ?
N3 C1A C6A 107.98(11) . . ?
C7A C1A C6A 109.84(11) . . ?
C2A C1A C6A 109.86(11) . . ?
C1A C2A C3A 108.59(12) . . ?
C1A C2A H2A 110.0 . . ?
C3A C2A H2A 110.0 . . ?
C1A C2A H2B 110.0 . . ?
C3A C2A H2B 110.0 . . ?
H2A C2A H2B 108.4 . . ?
C9A C3A C4A 109.75(13) . . ?
C9A C3A C2A 109.34(13) . . ?
C4A C3A C2A 109.32(12) . . ?
C9A C3A H3A 109.5 . . ?
C4A C3A H3A 109.5 . . ?
C2A C3A H3A 109.5 . . ?
C5A C4A C3A 109.61(12) . . ?
C5A C4A H4A 109.7 . . ?
C3A C4A H4A 109.7 . . ?
C5A C4A H4B 109.7 . . ?
C3A C4A H4B 109.7 . . ?
H4A C4A H4B 108.2 . . ?
C10A C5A C4A 109.64(12) . . ?
C10A C5A C6A 109.47(12) . . ?
C4A C5A C6A 109.16(12) . . ?
C10A C5A H5A 109.5 . . ?
C4A C5A H5A 109.5 . . ?
C6A C5A H5A 109.5 . . ?
C1A C6A C5A 108.82(11) . . ?
C1A C6A H6A 109.9 . . ?
C5A C6A H6A 109.9 . . ?
C1A C6A H6B 109.9 . . ?
C5A C6A H6B 109.9 . . ?
H6A C6A H6B 108.3 . . ?
C1A C7A C8A 108.93(11) . . ?
C1A C7A H7A 109.9 . . ?
C8A C7A H7A 109.9 . . ?
C1A C7A H7B 109.9 . . ?
C8A C7A H7B 109.9 . . ?
H7A C7A H7B 108.3 . . ?
C10A C8A C9A 109.81(12) . . ?
C10A C8A C7A 109.13(11) . . ?
C9A C8A C7A 109.11(12) . . ?
C10A C8A H8A 109.6 . . ?
C9A C8A H8A 109.6 . . ?
C7A C8A H8A 109.6 . . ?
C3A C9A C8A 109.69(12) . . ?
C3A C9A H9A 109.7 . . ?
C8A C9A H9A 109.7 . . ?
C3A C9A H9B 109.7 . . ?
C8A C9A H9B 109.7 . . ?
H9A C9A H9B 108.2 . . ?
C5A C10A C8A 109.69(12) . . ?
C5A C10A H10A 109.7 . . ?
C8A C10A H10A 109.7 . . ?
C5A C10A H10B 109.7 . . ?
C8A C10A H10B 109.7 . . ?
H10A C10A H10B 108.2 . . ?
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
O1 C1 1.2632(17) . ?
O2 C1 1.2672(19) . ?
C1 C2 1.5033(19) . ?
C2 C7 1.387(2) . ?
C2 C3 1.4264(19) . ?
C3 N4 1.3415(19) . ?
C3 N1 1.3748(19) . ?
N4 C5 1.341(2) . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
N1 C8 1.4006(19) . ?
N1 H1N 0.883(18) . ?
C8 C9 1.394(2) . ?
C8 C13 1.401(2) . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(2) . ?
C10 C14 1.456(7) . ?
C10 C141 1.534(6) . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 F2 1.299(4) . ?
C14 F1 1.305(5) . ?
C14 F3 1.309(6) . ?
C141 F21 1.299(4) . ?
C141 F11 1.302(5) . ?
C141 F31 1.307(6) . ?
N3 C1A 1.5124(17) . ?
N3 H3NA 0.945(19) . ?
N3 H3NB 0.991(19) . ?
N3 H3NC 0.964(19) . ?
C1A C7A 1.526(2) . ?
C1A C2A 1.526(2) . ?
C1A C6A 1.5329(18) . ?
C2A C3A 1.5413(19) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
C3A C9A 1.529(2) . ?
C3A C4A 1.535(2) . ?
C3A H3A 1.0000 . ?
C4A C5A 1.531(2) . ?
C4A H4A 0.9900 . ?
C4A H4B 0.9900 . ?
C5A C10A 1.530(2) . ?
C5A C6A 1.540(2) . ?
C5A H5A 1.0000 . ?
C6A H6A 0.9900 . ?
C6A H6B 0.9900 . ?
C7A C8A 1.5390(19) . ?
C7A H7A 0.9900 . ?
C7A H7B 0.9900 . ?
C8A C10A 1.5327(19) . ?
C8A C9A 1.535(2) . ?
C8A H8A 1.0000 . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
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
N1 H1N O2 0.883(18) 1.937(17) 2.6774(19) 140.6(16) .
C9 H9 N4 0.95 2.29 2.897(2) 120.8 .
N3 H3NA O1 0.945(19) 1.958(19) 2.8899(17) 168.2(16) 2_645
N3 H3NB O1 0.991(19) 1.82(2) 2.800(2) 168.8(16) 1_545
N3 H3NC O2 0.964(19) 1.815(19) 2.7745(18) 173.0(16) .
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 C1 C2 C7 23.61(18) . . . . ?
O2 C1 C2 C7 -157.88(12) . . . . ?
O1 C1 C2 C3 -155.91(12) . . . . ?
O2 C1 C2 C3 22.60(19) . . . . ?
C7 C2 C3 N4 0.60(19) . . . . ?
C1 C2 C3 N4 -179.87(12) . . . . ?
C7 C2 C3 N1 -179.13(12) . . . . ?
C1 C2 C3 N1 0.40(19) . . . . ?
N1 C3 N4 C5 179.48(12) . . . . ?
C2 C3 N4 C5 -0.25(19) . . . . ?
C3 N4 C5 C6 0.1(2) . . . . ?
N4 C5 C6 C7 -0.2(2) . . . . ?
C3 C2 C7 C6 -0.75(19) . . . . ?
C1 C2 C7 C6 179.71(12) . . . . ?
C5 C6 C7 C2 0.6(2) . . . . ?
N4 C3 N1 C8 -18.2(2) . . . . ?
C2 C3 N1 C8 161.57(13) . . . . ?
C3 N1 C8 C9 -1.3(2) . . . . ?
C3 N1 C8 C13 -179.61(13) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
N1 C8 C9 C10 -178.22(13) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
C8 C9 C10 C14 173.1(3) . . . . ?
C8 C9 C10 C141 -175.0(3) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C14 C10 C11 C12 -172.6(3) . . . . ?
C141 C10 C11 C12 175.0(3) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 C8 -0.4(2) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
N1 C8 C13 C12 178.78(13) . . . . ?
C11 C10 C14 F2 -14.9(7) . . . . ?
C9 C10 C14 F2 171.7(5) . . . . ?
C11 C10 C14 F1 -132.9(4) . . . . ?
C9 C10 C14 F1 53.6(6) . . . . ?
C11 C10 C14 F3 104.1(4) . . . . ?
C9 C10 C14 F3 -69.4(4) . . . . ?
C11 C10 C141 F21 18.9(5) . . . . ?
C9 C10 C141 F21 -166.3(3) . . . . ?
C11 C10 C141 F11 -99.7(6) . . . . ?
C9 C10 C141 F11 75.0(7) . . . . ?
C11 C10 C141 F31 142.5(5) . . . . ?
C9 C10 C141 F31 -42.7(6) . . . . ?
N3 C1A C2A C3A 179.45(11) . . . . ?
C7A C1A C2A C3A -60.28(15) . . . . ?
C6A C1A C2A C3A 61.18(15) . . . . ?
C1A C2A C3A C9A 59.86(15) . . . . ?
C1A C2A C3A C4A -60.32(16) . . . . ?
C9A C3A C4A C5A -59.60(16) . . . . ?
C2A C3A C4A C5A 60.32(16) . . . . ?
C3A C4A C5A C10A 59.72(15) . . . . ?
C3A C4A C5A C6A -60.20(15) . . . . ?
N3 C1A C6A C5A 179.68(11) . . . . ?
C7A C1A C6A C5A 60.67(15) . . . . ?
C2A C1A C6A C5A -61.29(15) . . . . ?
C10A C5A C6A C1A -59.79(15) . . . . ?
C4A C5A C6A C1A 60.23(15) . . . . ?
N3 C1A C7A C8A -179.35(11) . . . . ?
C2A C1A C7A C8A 60.37(14) . . . . ?
C6A C1A C7A C8A -61.11(14) . . . . ?
C1A C7A C8A C10A 60.42(15) . . . . ?
C1A C7A C8A C9A -59.56(15) . . . . ?
C4A C3A C9A C8A 59.22(15) . . . . ?
C2A C3A C9A C8A -60.69(15) . . . . ?
C10A C8A C9A C3A -59.13(15) . . . . ?
C7A C8A C9A C3A 60.44(15) . . . . ?
C4A C5A C10A C8A -59.64(15) . . . . ?
C6A C5A C10A C8A 60.08(15) . . . . ?
C9A C8A C10A C5A 59.32(15) . . . . ?
C7A C8A C10A C5A -60.24(15) . . . . ?
