#------------------------------------------------------------------------------
#$Date: 2022-08-02 01:37:03 +0300 (Tue, 02 Aug 2022) $
#$Revision: 277029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/52/7245238.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_7245238
loop_
_publ_author_name
'Haj Hassani Sohi, Takin'
'Maass, Felix Lasse Timon'
'Czekelius, Constantin'
'Suta, Markus'
'Vasylyeva, Vera'
_publ_section_title
;
 Co-crystallization of organic chromophore roseolumiflavin and effect on
 its optical characteristics
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00589A
_journal_year                    2022
_chemical_formula_moiety         'C14 H15 N5 O2, 1.5(C6 F4 I2)'
_chemical_formula_sum            'C23 H15 F6 I3 N5 O2'
_chemical_formula_weight         888.10
_chemical_name_common            'roseolumiflavin 1,4-diiodotetrafluorobenzene'
_chemical_name_systematic
'8-(dimethylamino)-7,10-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione 1,4-diiodotetrafluorobenzene'
_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   difmap
_audit_creation_date             2022-04-19
_audit_creation_method           'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_audit_update_record
;
2022-04-24 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                108.280(4)
_cell_angle_beta                 91.090(3)
_cell_angle_gamma                96.577(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7683(3)
_cell_length_b                   12.2451(5)
_cell_length_c                   14.6375(5)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1020
_cell_measurement_theta_min      3.0850
_cell_volume                     1311.17(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15384
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.301
_diffrn_reflns_theta_min         3.185
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    28.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.90a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    2.249
_exptl_crystal_description       plate
_exptl_crystal_F_000             834
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.761
_refine_diff_density_min         -1.355
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       0.00020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0342
_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)+(0.0487P)²+3.3321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4901
_reflns_number_total             5298
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00589a2.cif
_cod_data_source_block           R_B
_cod_database_code               7245238
_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_max   0.597
_shelx_estimated_absorpt_t_min   0.327
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
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
I1 I 0.56973(4) 0.54215(3) 0.21626(2) 0.02842(10) Uani 1 1 d . . . . .
F1 F 0.7604(4) 0.3704(3) 0.0481(2) 0.0411(8) Uani 1 1 d . . . . .
O1 O 0.7002(5) 0.7323(3) 0.3753(2) 0.0309(7) Uani 1 1 d . . . . .
N1 N 0.8854(5) 0.8550(4) 0.4929(3) 0.0251(8) Uani 1 1 d . . . . .
C1 C 0.4767(7) 0.4125(4) 0.0880(3) 0.0275(10) Uani 1 1 d . . . . .
H1 H 0.891(6) 0.911(4) 0.459(4) 0.013(11) Uiso 1 1 d . . . . .
I2 I 0.25063(4) 0.10258(3) -0.20551(2) 0.02728(10) Uani 1 1 d . . . . .
F2 F 0.6403(4) 0.2023(3) -0.1130(2) 0.0349(7) Uani 1 1 d . . . . .
O2 O 1.0616(5) 0.9846(3) 0.6107(2) 0.0296(7) Uani 1 1 d . . . . .
N2 N 0.7207(5) 0.5575(4) 0.4594(3) 0.0248(8) Uani 1 1 d . . . . .
C2 C 0.3018(6) 0.3861(5) 0.0625(3) 0.0289(10) Uani 1 1 d . . . . .
H2 H 0.918(8) 0.447(5) 0.699(5) 0.034(16) Uiso 1 1 d . . . . .
I3 I 0.77454(4) -0.09867(3) -0.18645(2) 0.03217(11) Uani 1 1 d . . . . .
F3 F 0.0670(4) 0.2756(3) -0.0405(2) 0.0446(8) Uani 1 1 d . . . . .
N3 N 0.9232(5) 0.6192(3) 0.6314(3) 0.0231(8) Uani 1 1 d . . . . .
C3 C 0.2394(7) 0.2969(5) -0.0191(4) 0.0309(11) Uani 1 1 d . . . . .
H3 H 0.605(8) 0.354(5) 0.408(4) 0.025(14) Uiso 1 1 d . . . . .
F4 F 0.1875(4) 0.4471(3) 0.1185(2) 0.0426(8) Uani 1 1 d . . . . .
N4 N 0.9874(5) 0.8085(3) 0.6289(3) 0.0250(8) Uani 1 1 d . . . . .
C4 C 0.3505(7) 0.2321(4) -0.0797(3) 0.0264(10) Uani 1 1 d . . . . .
H4A H 1.096(9) 0.723(6) 0.735(5) 0.035(16) Uiso 1 1 d . . . . .
H4B H 0.966(9) 0.646(6) 0.773(5) 0.040(17) Uiso 1 1 d . . . . .
H4C H 1.128(8) 0.594(6) 0.705(4) 0.033(15) Uiso 1 1 d . . . . .
F5 F 0.8384(4) 0.0919(3) 0.0219(2) 0.0389(7) Uani 1 1 d . . . . .
N5 N 0.7719(6) 0.2335(4) 0.6454(3) 0.0309(9) Uani 1 1 d . . . . .
C5 C 0.5263(6) 0.2601(4) -0.0558(3) 0.0253(9) Uani 1 1 d . . . . .
H5A H 0.844(11) 0.326(8) 0.789(6) 0.06(2) Uiso 1 1 d . . . . .
H5B H 1.003(11) 0.306(7) 0.717(5) 0.06(2) Uiso 1 1 d . . . . .
H5C H 0.900(8) 0.201(6) 0.750(5) 0.034(16) Uiso 1 1 d . . . . .
F6 F 0.3724(4) -0.1706(3) -0.1628(2) 0.0355(7) Uani 1 1 d . . . . .
C6 C 0.5884(6) 0.3486(4) 0.0280(3) 0.0276(10) Uani 1 1 d . . . . .
H6 H 0.537(9) 0.137(6) 0.608(5) 0.039(17) Uiso 1 1 d . . . . .
H6A H 0.701(9) 0.060(6) 0.585(5) 0.044(18) Uiso 1 1 d . . . . .
H6B H 0.647(10) 0.115(7) 0.693(6) 0.05(2) Uiso 1 1 d . . . . .
C7 C 0.6110(7) -0.0416(5) -0.0746(3) 0.0283(10) Uani 1 1 d . . . . .
H7A H 0.667(10) 0.098(7) 0.445(5) 0.05(2) Uiso 1 1 d . . . . .
H7B H 0.565(10) 0.153(6) 0.378(6) 0.05(2) Uiso 1 1 d . . . . .
H7C H 0.471(12) 0.143(7) 0.466(6) 0.07(2) Uiso 1 1 d . . . . .
C8 C 0.6714(6) 0.0452(5) 0.0098(4) 0.0285(10) Uani 1 1 d . . . . .
C9 C 0.4384(6) -0.0860(4) -0.0828(3) 0.0274(10) Uani 1 1 d . . . . .
C10 C 0.9821(6) 0.8856(4) 0.5799(3) 0.0239(9) Uani 1 1 d . . . . .
C11 C 0.9067(6) 0.7016(4) 0.5878(3) 0.0229(9) Uani 1 1 d . . . . .
C12 C 0.8395(6) 0.5074(4) 0.5927(3) 0.0235(9) Uani 1 1 d . . . . .
C13 C 0.8500(6) 0.4238(4) 0.6360(3) 0.0261(9) Uani 1 1 d . . . . .
C14 C 0.7605(6) 0.3099(4) 0.5968(4) 0.0279(10) Uani 1 1 d . . . . .
C15 C 0.6654(6) 0.2800(4) 0.5033(4) 0.0286(10) Uani 1 1 d . . . . .
C16 C 0.6568(7) 0.3658(4) 0.4635(3) 0.0273(10) Uani 1 1 d . . . . .
C17 C 0.7376(6) 0.4812(4) 0.5046(3) 0.0249(9) Uani 1 1 d . . . . .
C18 C 0.8024(6) 0.6653(4) 0.5002(3) 0.0245(9) Uani 1 1 d . . . . .
C19 C 0.7872(6) 0.7494(4) 0.4494(3) 0.0246(9) Uani 1 1 d . . . . .
C20 C 1.0416(7) 0.6482(5) 0.7182(4) 0.0300(10) Uani 1 1 d . . . . .
C21 C 0.8919(7) 0.2640(5) 0.7306(4) 0.0362(12) Uani 1 1 d . . . . .
C22 C 0.6505(8) 0.1283(5) 0.6312(5) 0.0392(12) Uani 1 1 d . . . . .
C23 C 0.5871(8) 0.1591(5) 0.4436(4) 0.0353(12) 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 0.0181 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'
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
C10 N1 H1 117(3) . . ?
C19 N1 H1 117(3) . . ?
C19 N1 C10 125.3(4) . . ?
C2 C1 I1 121.2(4) . . ?
C6 C1 I1 120.9(4) . . ?
C6 C1 C2 117.9(4) . . ?
C17 N2 C18 117.4(4) . . ?
C3 C2 C1 121.4(5) . . ?
F4 C2 C1 120.0(4) . . ?
F4 C2 C3 118.6(4) . . ?
C11 N3 C12 121.4(4) . . ?
C11 N3 C20 119.3(4) . . ?
C12 N3 C20 119.2(4) . . ?
C2 C3 C4 121.2(5) . . ?
F3 C3 C2 118.6(5) . . ?
F3 C3 C4 120.2(4) . . ?
C11 N4 C10 117.8(4) . . ?
C3 C4 I2 119.7(4) . . ?
C5 C4 I2 122.5(4) . . ?
C5 C4 C3 117.7(4) . . ?
C14 N5 C21 119.8(4) . . ?
C14 N5 C22 124.8(5) . . ?
C22 N5 C21 114.4(4) . . ?
F2 C5 C4 120.4(4) . . ?
F2 C5 C6 118.7(4) . . ?
C4 C5 C6 120.9(5) . . ?
F1 C6 C1 120.9(4) . . ?
F1 C6 C5 118.1(4) . . ?
C1 C6 C5 121.0(5) . . ?
C8 C7 I3 121.0(4) . . ?
C9 C7 I3 121.5(4) . . ?
C9 C7 C8 117.5(5) . . ?
F5 C8 C7 120.1(5) . . ?
F5 C8 C9 118.8(5) . 2_655 ?
C9 C8 C7 121.1(5) 2_655 . ?
F6 C9 C7 120.3(4) . . ?
F6 C9 C8 118.3(4) . 2_655 ?
C7 C9 C8 121.4(5) . 2_655 ?
O2 C10 N1 117.9(4) . . ?
O2 C10 N4 121.7(4) . . ?
N4 C10 N1 120.4(4) . . ?
N3 C11 C18 116.4(4) . . ?
N4 C11 N3 119.0(4) . . ?
N4 C11 C18 124.6(4) . . ?
N3 C12 C17 117.1(4) . . ?
C13 C12 N3 122.8(4) . . ?
C13 C12 C17 120.1(4) . . ?
C12 C13 H2 117(4) . . ?
C12 C13 C14 122.3(5) . . ?
C14 C13 H2 120(4) . . ?
N5 C14 C13 118.9(5) . . ?
N5 C14 C15 123.1(5) . . ?
C13 C14 C15 117.9(4) . . ?
C14 C15 C23 125.1(5) . . ?
C16 C15 C14 117.6(5) . . ?
C16 C15 C23 117.1(5) . . ?
C15 C16 H3 122(4) . . ?
C15 C16 C17 124.8(5) . . ?
C17 C16 H3 113(4) . . ?
N2 C17 C12 123.4(4) . . ?
N2 C17 C16 119.6(4) . . ?
C16 C17 C12 117.0(5) . . ?
N2 C18 C11 124.2(4) . . ?
N2 C18 C19 117.6(4) . . ?
C11 C18 C19 118.1(4) . . ?
O1 C19 N1 120.7(4) . . ?
O1 C19 C18 125.8(4) . . ?
N1 C19 C18 113.5(4) . . ?
N3 C20 H4A 112(4) . . ?
N3 C20 H4B 106(4) . . ?
N3 C20 H4C 108(4) . . ?
H4A C20 H4B 106(6) . . ?
H4A C20 H4C 110(6) . . ?
H4B C20 H4C 115(5) . . ?
N5 C21 H5A 110(4) . . ?
N5 C21 H5B 108(4) . . ?
N5 C21 H5C 110(4) . . ?
H5A C21 H5B 104(6) . . ?
H5A C21 H5C 107(6) . . ?
H5B C21 H5C 117(6) . . ?
N5 C22 H6 111(4) . . ?
N5 C22 H6A 109(4) . . ?
N5 C22 H6B 107(5) . . ?
H6 C22 H6A 112(6) . . ?
H6 C22 H6B 112(6) . . ?
H6A C22 H6B 107(6) . . ?
H7A C23 H7B 107(6) . . ?
H7A C23 H7C 113(6) . . ?
H7B C23 H7C 104(7) . . ?
C15 C23 H7A 112(4) . . ?
C15 C23 H7B 112(5) . . ?
C15 C23 H7C 109(5) . . ?
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
I1 C1 2.094(5) . ?
F1 C6 1.341(6) . ?
O1 C19 1.214(6) . ?
N1 H1 0.97(5) . ?
N1 C10 1.388(6) . ?
N1 C19 1.378(6) . ?
C1 C2 1.376(7) . ?
C1 C6 1.375(7) . ?
I2 C4 2.083(5) . ?
F2 C5 1.337(6) . ?
O2 C10 1.236(6) . ?
N2 C17 1.319(6) . ?
N2 C18 1.342(6) . ?
C2 C3 1.376(7) . ?
C2 F4 1.346(6) . ?
I3 C7 2.085(5) . ?
F3 C3 1.346(6) . ?
N3 C11 1.368(6) . ?
N3 C12 1.383(6) . ?
N3 C20 1.478(6) . ?
C3 C4 1.381(7) . ?
N4 C10 1.357(6) . ?
N4 C11 1.332(6) . ?
C4 C5 1.380(7) . ?
F5 C8 1.342(6) . ?
N5 C14 1.351(7) . ?
N5 C21 1.466(7) . ?
N5 C22 1.462(7) . ?
C5 C6 1.391(7) . ?
F6 C9 1.342(6) . ?
C7 C8 1.384(7) . ?
C7 C9 1.376(7) . ?
C8 C9 1.384(7) 2_655 ?
C9 C8 1.384(7) 2_655 ?
C11 C18 1.420(6) . ?
C12 C13 1.371(7) . ?
C12 C17 1.428(7) . ?
C13 H2 1.00(7) . ?
C13 C14 1.420(7) . ?
C14 C15 1.463(7) . ?
C15 C16 1.357(7) . ?
C15 C23 1.512(7) . ?
C16 H3 0.86(6) . ?
C16 C17 1.415(7) . ?
C18 C19 1.460(7) . ?
C20 H4A 0.92(7) . ?
C20 H4B 1.02(7) . ?
C20 H4C 0.98(7) . ?
C21 H5A 1.05(9) . ?
C21 H5B 1.01(8) . ?
C21 H5C 0.90(7) . ?
C22 H6 0.97(7) . ?
C22 H6A 1.02(7) . ?
C22 H6B 0.97(8) . ?
C23 H7A 1.02(8) . ?
C23 H7B 0.94(8) . ?
C23 H7C 0.99(9) . ?
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
I1 C1 C2 C3 -176.5(4) . . . . ?
I1 C1 C2 F4 2.6(7) . . . . ?
I1 C1 C6 F1 -2.5(7) . . . . ?
I1 C1 C6 C5 178.1(4) . . . . ?
C1 C2 C3 F3 -179.7(5) . . . . ?
C1 C2 C3 C4 -1.5(9) . . . . ?
I2 C4 C5 F2 -1.2(7) . . . . ?
I2 C4 C5 C6 178.8(4) . . . . ?
F2 C5 C6 F1 -1.0(7) . . . . ?
F2 C5 C6 C1 178.4(4) . . . . ?
N2 C18 C19 O1 3.7(7) . . . . ?
N2 C18 C19 N1 -175.5(4) . . . . ?
C2 C1 C6 F1 179.4(5) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
C2 C3 C4 I2 -177.4(4) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
I3 C7 C8 F5 -1.8(7) . . . . ?
I3 C7 C8 C9 177.8(4) . . . 2_655 ?
I3 C7 C9 F6 2.1(7) . . . . ?
I3 C7 C9 C8 -177.8(4) . . . 2_655 ?
F3 C3 C4 I2 0.8(7) . . . . ?
F3 C3 C4 C5 178.0(5) . . . . ?
N3 C11 C18 N2 0.3(7) . . . . ?
N3 C11 C18 C19 -177.6(4) . . . . ?
N3 C12 C13 C14 178.6(4) . . . . ?
N3 C12 C17 N2 0.1(7) . . . . ?
N3 C12 C17 C16 178.0(4) . . . . ?
C3 C4 C5 F2 -178.3(5) . . . . ?
C3 C4 C5 C6 1.7(8) . . . . ?
F4 C2 C3 F3 1.2(8) . . . . ?
F4 C2 C3 C4 179.4(5) . . . . ?
N4 C11 C18 N2 -179.6(4) . . . . ?
N4 C11 C18 C19 2.4(7) . . . . ?
C4 C5 C6 F1 178.9(5) . . . . ?
C4 C5 C6 C1 -1.6(8) . . . . ?
N5 C14 C15 C16 177.1(5) . . . . ?
N5 C14 C15 C23 -7.7(8) . . . . ?
C6 C1 C2 C3 1.5(8) . . . . ?
C6 C1 C2 F4 -179.3(5) . . . . ?
C8 C7 C9 F6 -179.8(4) . . . . ?
C8 C7 C9 C8 0.3(8) . . . 2_655 ?
C9 C7 C8 F5 -179.9(4) . . . . ?
C9 C7 C8 C9 -0.3(8) . . . 2_655 ?
C10 N1 C19 O1 176.5(4) . . . . ?
C10 N1 C19 C18 -4.3(7) . . . . ?
C10 N4 C11 N3 174.1(4) . . . . ?
C10 N4 C11 C18 -5.9(7) . . . . ?
C11 N3 C12 C13 -178.3(4) . . . . ?
C11 N3 C12 C17 1.0(6) . . . . ?
C11 N4 C10 N1 4.3(7) . . . . ?
C11 N4 C10 O2 -176.0(4) . . . . ?
C11 C18 C19 O1 -178.2(5) . . . . ?
C11 C18 C19 N1 2.6(6) . . . . ?
C12 N3 C11 N4 178.8(4) . . . . ?
C12 N3 C11 C18 -1.2(6) . . . . ?
C12 C13 C14 N5 -177.6(4) . . . . ?
C12 C13 C14 C15 4.7(7) . . . . ?
C13 C12 C17 N2 179.5(4) . . . . ?
C13 C12 C17 C16 -2.7(7) . . . . ?
C13 C14 C15 C16 -5.3(7) . . . . ?
C13 C14 C15 C23 169.9(5) . . . . ?
C14 C15 C16 C17 2.0(7) . . . . ?
C15 C16 C17 N2 179.9(5) . . . . ?
C15 C16 C17 C12 2.0(7) . . . . ?
C17 N2 C18 C11 0.7(7) . . . . ?
C17 N2 C18 C19 178.7(4) . . . . ?
C17 C12 C13 C14 -0.7(7) . . . . ?
C18 N2 C17 C12 -1.0(7) . . . . ?
C18 N2 C17 C16 -178.8(4) . . . . ?
C19 N1 C10 O2 -178.8(4) . . . . ?
C19 N1 C10 N4 1.0(7) . . . . ?
C20 N3 C11 N4 -5.2(6) . . . . ?
C20 N3 C11 C18 174.8(4) . . . . ?
C20 N3 C12 C13 5.6(7) . . . . ?
C20 N3 C12 C17 -175.0(4) . . . . ?
C21 N5 C14 C13 -7.4(7) . . . . ?
C21 N5 C14 C15 170.1(5) . . . . ?
C22 N5 C14 C13 160.6(5) . . . . ?
C22 N5 C14 C15 -21.8(8) . . . . ?
C23 C15 C16 C17 -173.5(5) . . . . ?
