#------------------------------------------------------------------------------
#$Date: 2024-10-18 18:16:49 +0300 (Fri, 18 Oct 2024) $
#$Revision: 295543 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246216.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_7246216
loop_
_publ_author_name
'Das, Rajorshi'
'Linseis, Michael'
'Schupp, Stefan M.'
'Gogesch, Franciska S.'
'Schmidt-Mende, Lukas'
'Winter, Rainer F.'
_publ_section_title
;
 Organic binary charge-transfer compounds of
 2,2′ : 6′,2′′ : 6′′,6-trioxotriphenylamine
 and a pyrene-annulated azaacene as donors
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3652
_journal_page_last               3660
_journal_paper_doi               10.1039/D2RA07322F
_journal_volume                  13
_journal_year                    2023
_chemical_compound_source        Dichloromethane
_chemical_formula_moiety         '0.5(C H2 Cl2), C12 F4 N4, C18 H9 N O3'
_chemical_formula_sum            'C30.5 H10 Cl F4 N5 O3'
_chemical_formula_weight         605.88
_chemical_name_systematic        'PAA F4TCNQ'
_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     dual
_audit_creation_date             2022-11-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-11-17 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.490(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1173(6)
_cell_length_b                   19.0311(5)
_cell_length_c                   16.1480(6)
_cell_measurement_reflns_used    34532
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      1.84
_cell_volume                     4959.0(3)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.86, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
 153 frames, detector distance = 80 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29782
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.690
_diffrn_reflns_theta_min         1.844
_diffrn_source
'Sealed Mo X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9174
_exptl_absorpt_correction_T_min  0.5802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2440
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00144(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     785
_refine_ls_number_reflns         11385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0488
_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)+(0.0411P)²+6.1486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8149
_reflns_number_total             11385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra07322f2.cif
_cod_data_source_block           raj151
_cod_depositor_comments
;

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C61 H20 Cl2 F8 N10 O6'
_cod_original_formula_weight         1211.77
_cod_original_formula_moiety         'C H2 Cl2, 2(C12 F4 N4), 2(C18 H9 N O3)'
_cod_original_formula_units_Z            4
_cod_database_code               7246216
_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_max   0.955
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B)
2.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C23(H23), C27(H27), C21(H21), C3(H3), C33(H33), C35(H35), C9(H9),
 C28(H28), C10(H10), C22(H22), C11(H11), C4(H4), C34(H34), C5(H5), C17(H17),
 C15(H15), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl2 Cl 0.49514(5) 0.07327(6) 0.90464(5) 0.0626(2) Uani 1 1 d . . . . .
Cl1 Cl 0.47171(5) -0.07353(6) 0.84761(6) 0.0641(2) Uani 1 1 d . . . . .
F3 F 0.26698(8) 0.52848(7) 0.37095(8) 0.0279(3) Uani 1 1 d . . . . .
F8 F 0.08413(8) 0.64235(7) 0.41009(8) 0.0284(3) Uani 1 1 d . . . . .
F2 F 0.31882(9) 0.35238(7) 0.59036(8) 0.0300(3) Uani 1 1 d . . . . .
F6 F 0.11647(9) 0.36958(7) 0.50995(8) 0.0298(3) Uani 1 1 d . . . . .
F4 F 0.27700(8) 0.62461(7) 0.48901(8) 0.0283(3) Uani 1 1 d . . . . .
F1 F 0.32906(9) 0.44900(7) 0.70898(8) 0.0298(3) Uani 1 1 d . . . . .
F7 F 0.07349(8) 0.54632(7) 0.29207(8) 0.0283(3) Uani 1 1 d . . . . .
F5 F 0.12535(9) 0.46566(7) 0.62806(8) 0.0290(3) Uani 1 1 d . . . . .
O5 O 0.06392(9) 0.17399(8) 0.50812(10) 0.0238(3) Uani 1 1 d . . . . .
O6 O 0.32208(9) 0.25103(9) 0.71926(10) 0.0267(3) Uani 1 1 d . . . . .
O4 O 0.32251(9) 0.08040(8) 0.49849(10) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.12269(9) -0.18090(8) 0.39205(10) 0.0265(3) Uani 1 1 d . . . . .
O3 O 0.36590(10) -0.08971(10) 0.61453(11) 0.0362(4) Uani 1 1 d . . . . .
O1 O 0.39329(11) -0.26832(10) 0.41438(12) 0.0371(4) Uani 1 1 d . . . . .
N2 N 0.23613(11) 0.16878(10) 0.57470(11) 0.0224(4) Uani 1 1 d . . . . .
N3 N 0.28265(12) 0.24879(10) 0.43502(12) 0.0280(4) Uani 1 1 d . . . . .
N1 N 0.29363(11) -0.17957(10) 0.47349(12) 0.0259(4) Uani 1 1 d . . . . .
N4 N 0.28208(12) 0.40999(11) 0.25224(12) 0.0289(4) Uani 1 1 d . . . . .
N10 N 0.11795(13) 0.58669(11) 0.74837(13) 0.0311(4) Uani 1 1 d . . . . .
N8 N 0.08138(13) 0.42362(11) 0.17156(13) 0.0311(4) Uani 1 1 d . . . . .
N6 N 0.32374(13) 0.57723(11) 0.83109(13) 0.0317(4) Uani 1 1 d . . . . .
N7 N 0.07085(13) 0.26765(11) 0.35490(13) 0.0326(5) Uani 1 1 d . . . . .
N5 N 0.32852(13) 0.72761(11) 0.64377(13) 0.0321(4) Uani 1 1 d . . . . .
N9 N 0.12130(14) 0.74518(11) 0.56356(13) 0.0360(5) Uani 1 1 d . . . . .
C37 C 0.30287(12) 0.54261(11) 0.60578(13) 0.0211(4) Uani 1 1 d . . . . .
C26 C 0.23662(13) 0.25366(12) 0.68510(14) 0.0232(4) Uani 1 1 d . . . . .
C19 C 0.19383(13) 0.12846(11) 0.50349(14) 0.0225(4) Uani 1 1 d . . . . .
C43 C 0.28261(13) 0.38216(11) 0.40850(14) 0.0227(4) Uani 1 1 d . . . . .
C20 C 0.23708(13) 0.08486(12) 0.46424(14) 0.0241(4) Uani 1 1 d . . . . .
C25 C 0.19347(13) 0.21245(12) 0.61258(14) 0.0227(4) Uani 1 1 d . . . . .
C38 C 0.28855(13) 0.55721(11) 0.51597(14) 0.0222(4) Uani 1 1 d . . . . .
C51 C 0.08680(13) 0.52493(12) 0.37508(13) 0.0230(4) Uani 1 1 d . . . . .
C56 C 0.08445(13) 0.41486(12) 0.24305(14) 0.0246(5) Uani 1 1 d . . . . .
C39 C 0.28338(13) 0.50707(12) 0.45447(13) 0.0217(4) Uani 1 1 d . . . . .
C44 C 0.28199(13) 0.39894(11) 0.32228(14) 0.0233(4) Uani 1 1 d . . . . .
C40 C 0.29077(12) 0.43463(11) 0.47329(13) 0.0211(4) Uani 1 1 d . . . . .
C55 C 0.09024(13) 0.39943(11) 0.33138(14) 0.0226(4) Uani 1 1 d . . . . .
C49 C 0.10589(12) 0.56009(11) 0.52660(13) 0.0210(4) Uani 1 1 d . . . . .
C46 C 0.30791(13) 0.59580(12) 0.66851(14) 0.0233(4) Uani 1 1 d . . . . .
C58 C 0.11411(13) 0.61230(11) 0.59062(14) 0.0224(4) Uani 1 1 d . . . . .
C32 C 0.36392(14) 0.12086(12) 0.57004(14) 0.0255(5) Uani 1 1 d . . . . .
C24 C 0.10718(13) 0.13178(11) 0.47008(14) 0.0233(4) Uani 1 1 d . . . . .
C30 C 0.10709(13) 0.21429(11) 0.57943(13) 0.0223(4) Uani 1 1 d . . . . .
C54 C 0.11113(13) 0.48699(12) 0.54484(13) 0.0220(4) Uani 1 1 d . . . . .
C45 C 0.28322(13) 0.30891(12) 0.42565(14) 0.0229(4) Uani 1 1 d . . . . .
C59 C 0.11696(13) 0.59656(11) 0.67764(14) 0.0238(4) Uani 1 1 d . . . . .
C29 C 0.06370(14) 0.25618(12) 0.61801(14) 0.0246(5) Uani 1 1 d . . . . .
H29 H 0.006081 0.257116 0.596695 0.030 Uiso 1 1 calc R U . . .
C41 C 0.30647(13) 0.41965(11) 0.56351(14) 0.0224(4) Uani 1 1 d . . . . .
C50 C 0.09217(13) 0.57490(11) 0.43660(14) 0.0216(4) Uani 1 1 d . . . . .
C31 C 0.32132(13) 0.16639(12) 0.60842(14) 0.0241(4) Uani 1 1 d . . . . .
C52 C 0.09393(12) 0.45186(11) 0.39391(13) 0.0211(4) Uani 1 1 d . . . . .
C7 C 0.24454(14) -0.13518(12) 0.50201(14) 0.0247(5) Uani 1 1 d . . . . .
C23 C 0.06455(14) 0.09248(12) 0.39733(15) 0.0262(5) Uani 1 1 d . . . . .
H23 H 0.007055 0.094575 0.373926 0.031 Uiso 1 1 calc R U . . .
C36 C 0.36373(14) 0.20803(12) 0.68011(14) 0.0261(5) Uani 1 1 d . . . . .
C8 C 0.15875(14) -0.13596(12) 0.46059(14) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.17290(14) -0.22230(12) 0.36123(14) 0.0259(5) Uani 1 1 d . . . . .
C47 C 0.31613(13) 0.58256(12) 0.75789(14) 0.0251(5) Uani 1 1 d . . . . .
C42 C 0.31185(13) 0.46981(12) 0.62514(13) 0.0218(4) Uani 1 1 d . . . . .
C60 C 0.11701(14) 0.68549(12) 0.57338(14) 0.0254(5) Uani 1 1 d . . . . .
C48 C 0.31794(13) 0.66855(13) 0.65177(14) 0.0253(5) Uani 1 1 d . . . . .
C53 C 0.10626(13) 0.43716(11) 0.48336(14) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.25844(14) -0.22271(12) 0.40251(14) 0.0262(5) Uani 1 1 d . . . . .
C27 C 0.19401(14) 0.29637(12) 0.72357(14) 0.0267(5) Uani 1 1 d . . . . .
H27 H 0.222222 0.324310 0.771468 0.032 Uiso 1 1 calc R U . . .
C57 C 0.08093(14) 0.32671(12) 0.34693(14) 0.0252(5) Uani 1 1 d . . . . .
C21 C 0.19530(15) 0.04550(12) 0.39208(15) 0.0283(5) Uani 1 1 d . . . . .
H21 H 0.223640 0.016627 0.365260 0.034 Uiso 1 1 calc R U . . .
C13 C 0.37854(14) -0.17928(13) 0.51418(15) 0.0302(5) Uani 1 1 d . . . . .
C3 C 0.13769(16) -0.26349(12) 0.28834(15) 0.0301(5) Uani 1 1 d . . . . .
H3 H 0.080696 -0.263008 0.259643 0.036 Uiso 1 1 calc R U . . .
C12 C 0.28062(14) -0.09066(13) 0.57350(15) 0.0291(5) Uani 1 1 d . . . . .
C33 C 0.44912(14) 0.11720(14) 0.60431(15) 0.0308(5) Uani 1 1 d . . . . .
H33 H 0.478508 0.086571 0.580765 0.037 Uiso 1 1 calc R U . . .
C35 C 0.44926(14) 0.20582(14) 0.71342(16) 0.0313(5) Uani 1 1 d . . . . .
H35 H 0.478593 0.234122 0.760471 0.038 Uiso 1 1 calc R U . . .
C14 C 0.42739(15) -0.22514(14) 0.48494(17) 0.0343(6) Uani 1 1 d . . . . .
C6 C 0.30867(15) -0.26621(13) 0.37195(16) 0.0300(5) Uani 1 1 d . . . . .
C9 C 0.10934(15) -0.09183(12) 0.48888(15) 0.0281(5) Uani 1 1 d . . . . .
H9 H 0.052241 -0.091127 0.460888 0.034 Uiso 1 1 calc R U . . .
C18 C 0.41363(15) -0.13433(14) 0.58494(16) 0.0333(5) Uani 1 1 d . . . . .
C28 C 0.10774(15) 0.29718(12) 0.68967(15) 0.0271(5) Uani 1 1 d . . . . .
H28 H 0.078728 0.326027 0.715752 0.033 Uiso 1 1 calc R U . . .
C10 C 0.14645(16) -0.04837(13) 0.56009(16) 0.0314(5) Uani 1 1 d . . . . .
H10 H 0.113021 -0.018973 0.579898 0.038 Uiso 1 1 calc R U . . .
C22 C 0.10902(15) 0.04992(12) 0.35992(15) 0.0289(5) Uani 1 1 d . . . . .
H22 H 0.080211 0.023059 0.311186 0.035 Uiso 1 1 calc R U . . .
C11 C 0.23197(16) -0.04697(13) 0.60326(16) 0.0329(5) Uani 1 1 d . . . . .
H11 H 0.255315 -0.017267 0.650846 0.039 Uiso 1 1 calc R U . . .
C4 C 0.18874(17) -0.30592(13) 0.25822(16) 0.0352(6) Uani 1 1 d . . . . .
H4 H 0.165060 -0.333820 0.208913 0.042 Uiso 1 1 calc R U . . .
C34 C 0.49009(15) 0.16034(14) 0.67488(16) 0.0340(6) Uani 1 1 d . . . . .
H34 H 0.547653 0.158576 0.697251 0.041 Uiso 1 1 calc R U . . .
C5 C 0.27421(17) -0.30781(13) 0.29976(16) 0.0352(6) Uani 1 1 d . . . . .
H5 H 0.307277 -0.336763 0.278888 0.042 Uiso 1 1 calc R U . . .
C17 C 0.49875(16) -0.13445(17) 0.62638(17) 0.0435(7) Uani 1 1 d . . . . .
H17 H 0.523590 -0.104245 0.673031 0.052 Uiso 1 1 calc R U . . .
C15 C 0.51202(16) -0.22645(17) 0.52728(18) 0.0417(7) Uani 1 1 d . . . . .
H15 H 0.545333 -0.257431 0.509485 0.050 Uiso 1 1 calc R U . . .
C16 C 0.54623(16) -0.18109(18) 0.59630(19) 0.0468(7) Uani 1 1 d . . . . .
H16 H 0.603370 -0.181537 0.624044 0.056 Uiso 1 1 calc R U . . .
C61 C 0.47072(18) 0.01490(19) 0.81470(19) 0.0530(8) Uani 1 1 d . . . . .
H61A H 0.416231 0.026295 0.773896 0.064 Uiso 1 1 calc R U . . .
H61B H 0.510461 0.020971 0.784261 0.064 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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'
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
C24 O5 C30 118.87(17) . . ?
C36 O6 C26 118.82(17) . . ?
C32 O4 C20 118.85(17) . . ?
C8 O2 C2 118.80(17) . . ?
C18 O3 C12 118.70(19) . . ?
C14 O1 C6 118.77(19) . . ?
C19 N2 C25 120.03(18) . . ?
C19 N2 C31 120.43(19) . . ?
C31 N2 C25 119.54(19) . . ?
C7 N1 C13 120.1(2) . . ?
C1 N1 C7 119.97(19) . . ?
C1 N1 C13 119.9(2) . . ?
C38 C37 C42 112.76(19) . . ?
C46 C37 C38 122.8(2) . . ?
C46 C37 C42 124.44(19) . . ?
O6 C26 C25 120.47(19) . . ?
C27 C26 O6 119.5(2) . . ?
C27 C26 C25 120.0(2) . . ?
N2 C19 C20 120.1(2) . . ?
N2 C19 C24 119.5(2) . . ?
C20 C19 C24 120.4(2) . . ?
C40 C43 C44 122.0(2) . . ?
C40 C43 C45 123.66(19) . . ?
C45 C43 C44 114.05(19) . . ?
O4 C20 C19 120.3(2) . . ?
C21 C20 O4 119.3(2) . . ?
C21 C20 C19 120.4(2) . . ?
N2 C25 C26 120.03(19) . . ?
N2 C25 C30 119.7(2) . . ?
C30 C25 C26 120.2(2) . . ?
F4 C38 C37 118.32(19) . . ?
F4 C38 C39 117.75(18) . . ?
C39 C38 C37 123.9(2) . . ?
F7 C51 C50 117.73(19) . . ?
F7 C51 C52 118.91(19) . . ?
C50 C51 C52 123.36(19) . . ?
N8 C56 C55 176.2(3) . . ?
F3 C39 C38 117.43(19) . . ?
F3 C39 C40 119.10(19) . . ?
C38 C39 C40 123.41(19) . . ?
N4 C44 C43 177.5(2) . . ?
C43 C40 C41 123.6(2) . . ?
C39 C40 C43 123.38(19) . . ?
C39 C40 C41 113.00(19) . . ?
C52 C55 C56 122.9(2) . . ?
C52 C55 C57 122.93(19) . . ?
C57 C55 C56 113.67(19) . . ?
C58 C49 C54 123.80(19) . . ?
C58 C49 C50 123.6(2) . . ?
C54 C49 C50 112.60(19) . . ?
C37 C46 C47 124.1(2) . . ?
C37 C46 C48 122.64(19) . . ?
C47 C46 C48 112.62(19) . . ?
C49 C58 C59 122.7(2) . . ?
C49 C58 C60 123.3(2) . . ?
C59 C58 C60 114.04(19) . . ?
O4 C32 C31 121.3(2) . . ?
O4 C32 C33 119.3(2) . . ?
C33 C32 C31 119.3(2) . . ?
O5 C24 C19 121.03(19) . . ?
O5 C24 C23 119.28(19) . . ?
C23 C24 C19 119.7(2) . . ?
O5 C30 C25 120.78(19) . . ?
C29 C30 O5 118.87(19) . . ?
C29 C30 C25 120.3(2) . . ?
F5 C54 C49 118.75(18) . . ?
F5 C54 C53 117.82(19) . . ?
C53 C54 C49 123.36(19) . . ?
N3 C45 C43 176.5(2) . . ?
N10 C59 C58 177.0(2) . . ?
C30 C29 H29 120.7 . . ?
C30 C29 C28 118.6(2) . . ?
C28 C29 H29 120.7 . . ?
F2 C41 C40 118.52(19) . . ?
F2 C41 C42 117.85(18) . . ?
C42 C41 C40 123.6(2) . . ?
F8 C50 C51 117.46(18) . . ?
F8 C50 C49 118.63(19) . . ?
C51 C50 C49 123.9(2) . . ?
N2 C31 C32 118.9(2) . . ?
N2 C31 C36 120.0(2) . . ?
C36 C31 C32 121.1(2) . . ?
C55 C52 C51 124.14(19) . . ?
C55 C52 C53 123.2(2) . . ?
C53 C52 C51 112.63(19) . . ?
N1 C7 C8 119.7(2) . . ?
N1 C7 C12 119.9(2) . . ?
C8 C7 C12 120.4(2) . . ?
C24 C23 H23 120.7 . . ?
C24 C23 C22 118.6(2) . . ?
C22 C23 H23 120.7 . . ?
O6 C36 C31 121.1(2) . . ?
O6 C36 C35 119.0(2) . . ?
C35 C36 C31 119.8(2) . . ?
O2 C8 C7 120.8(2) . . ?
O2 C8 C9 119.2(2) . . ?
C9 C8 C7 120.0(2) . . ?
O2 C2 C1 121.0(2) . . ?
C3 C2 O2 119.2(2) . . ?
C3 C2 C1 119.8(2) . . ?
N6 C47 C46 174.8(2) . . ?
F1 C42 C37 118.75(19) . . ?
F1 C42 C41 117.92(19) . . ?
C41 C42 C37 123.30(19) . . ?
N9 C60 C58 176.8(2) . . ?
N5 C48 C46 175.8(2) . . ?
F6 C53 C54 117.66(18) . . ?
F6 C53 C52 118.20(19) . . ?
C54 C53 C52 124.1(2) . . ?
N1 C1 C2 119.6(2) . . ?
N1 C1 C6 119.9(2) . . ?
C2 C1 C6 120.5(2) . . ?
C26 C27 H27 120.6 . . ?
C26 C27 C28 118.9(2) . . ?
C28 C27 H27 120.6 . . ?
N7 C57 C55 176.4(2) . . ?
C20 C21 H21 120.9 . . ?
C20 C21 C22 118.1(2) . . ?
C22 C21 H21 120.9 . . ?
N1 C13 C14 119.4(2) . . ?
N1 C13 C18 119.4(2) . . ?
C18 C13 C14 121.2(2) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.9(2) . . ?
C4 C3 H3 120.6 . . ?
O3 C12 C7 120.4(2) . . ?
C11 C12 O3 119.3(2) . . ?
C11 C12 C7 120.2(2) . . ?
C32 C33 H33 120.8 . . ?
C32 C33 C34 118.4(2) . . ?
C34 C33 H33 120.8 . . ?
C36 C35 H35 120.9 . . ?
C36 C35 C34 118.2(2) . . ?
C34 C35 H35 120.9 . . ?
O1 C14 C13 121.3(2) . . ?
O1 C14 C15 119.2(2) . . ?
C15 C14 C13 119.5(3) . . ?
O1 C6 C1 120.6(2) . . ?
C5 C6 O1 119.2(2) . . ?
C5 C6 C1 120.2(2) . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.5(2) . . ?
C10 C9 H9 120.7 . . ?
O3 C18 C13 121.5(2) . . ?
O3 C18 C17 119.1(2) . . ?
C17 C18 C13 119.4(3) . . ?
C29 C28 C27 122.0(2) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.6(2) . . ?
C11 C10 H10 118.7 . . ?
C23 C22 C21 122.8(2) . . ?
C23 C22 H22 118.6 . . ?
C21 C22 H22 118.6 . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.9(2) . . ?
C5 C4 H4 119.1 . . ?
C33 C34 H34 118.5 . . ?
C35 C34 C33 123.1(2) . . ?
C35 C34 H34 118.5 . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C18 C17 H17 120.9 . . ?
C18 C17 C16 118.3(3) . . ?
C16 C17 H17 120.9 . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C17 C16 H16 118.6 . . ?
C15 C16 C17 122.7(3) . . ?
C15 C16 H16 118.6 . . ?
Cl2 C61 H61A 109.2 . . ?
Cl2 C61 H61B 109.2 . . ?
Cl1 C61 Cl2 112.15(16) . . ?
Cl1 C61 H61A 109.2 . . ?
Cl1 C61 H61B 109.2 . . ?
H61A C61 H61B 107.9 . . ?
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
Cl2 C61 1.764(3) . ?
Cl1 C61 1.763(4) . ?
F3 C39 1.346(2) . ?
F8 C50 1.346(2) . ?
F2 C41 1.345(2) . ?
F6 C53 1.349(2) . ?
F4 C38 1.348(2) . ?
F1 C42 1.346(2) . ?
F7 C51 1.346(2) . ?
F5 C54 1.346(2) . ?
O5 C24 1.369(3) . ?
O5 C30 1.376(3) . ?
O6 C26 1.381(3) . ?
O6 C36 1.370(3) . ?
O4 C20 1.383(3) . ?
O4 C32 1.372(3) . ?
O2 C8 1.372(3) . ?
O2 C2 1.376(3) . ?
O3 C12 1.387(3) . ?
O3 C18 1.370(3) . ?
O1 C14 1.368(3) . ?
O1 C6 1.381(3) . ?
N2 C19 1.371(3) . ?
N2 C25 1.377(3) . ?
N2 C31 1.377(3) . ?
N3 C45 1.155(3) . ?
N1 C7 1.375(3) . ?
N1 C1 1.375(3) . ?
N1 C13 1.381(3) . ?
N4 C44 1.151(3) . ?
N10 C59 1.152(3) . ?
N8 C56 1.150(3) . ?
N6 C47 1.150(3) . ?
N7 C57 1.151(3) . ?
N5 C48 1.153(3) . ?
N9 C60 1.153(3) . ?
C37 C38 1.415(3) . ?
C37 C46 1.414(3) . ?
C37 C42 1.417(3) . ?
C26 C25 1.398(3) . ?
C26 C27 1.371(3) . ?
C19 C20 1.397(3) . ?
C19 C24 1.400(3) . ?
C43 C44 1.425(3) . ?
C43 C40 1.419(3) . ?
C43 C45 1.421(3) . ?
C20 C21 1.369(3) . ?
C25 C30 1.395(3) . ?
C38 C39 1.359(3) . ?
C51 C50 1.356(3) . ?
C51 C52 1.420(3) . ?
C56 C55 1.427(3) . ?
C39 C40 1.408(3) . ?
C40 C41 1.419(3) . ?
C55 C52 1.406(3) . ?
C55 C57 1.425(3) . ?
C49 C58 1.407(3) . ?
C49 C54 1.419(3) . ?
C49 C50 1.421(3) . ?
C46 C47 1.425(3) . ?
C46 C48 1.432(3) . ?
C58 C59 1.422(3) . ?
C58 C60 1.424(3) . ?
C32 C31 1.403(3) . ?
C32 C33 1.378(3) . ?
C24 C23 1.378(3) . ?
C30 C29 1.373(3) . ?
C54 C53 1.355(3) . ?
C29 H29 0.9300 . ?
C29 C28 1.391(3) . ?
C41 C42 1.360(3) . ?
C31 C36 1.391(3) . ?
C52 C53 1.416(3) . ?
C7 C8 1.396(3) . ?
C7 C12 1.399(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.381(3) . ?
C36 C35 1.382(3) . ?
C8 C9 1.374(3) . ?
C2 C1 1.392(3) . ?
C2 C3 1.375(3) . ?
C1 C6 1.397(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.393(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.395(3) . ?
C13 C14 1.396(4) . ?
C13 C18 1.393(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(4) . ?
C12 C11 1.372(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.390(4) . ?
C35 H35 0.9300 . ?
C35 C34 1.384(4) . ?
C14 C15 1.380(3) . ?
C6 C5 1.369(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(3) . ?
C18 C17 1.386(3) . ?
C28 H28 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.396(4) . ?
C22 H22 0.9300 . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.392(4) . ?
C34 H34 0.9300 . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.396(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(4) . ?
C16 H16 0.9300 . ?
C61 H61A 0.9700 . ?
C61 H61B 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
F3 C39 C40 C43 0.6(3) . . . . ?
F3 C39 C40 C41 -178.84(17) . . . . ?
F2 C41 C42 F1 -0.1(3) . . . . ?
F2 C41 C42 C37 177.84(19) . . . . ?
F4 C38 C39 F3 -0.1(3) . . . . ?
F4 C38 C39 C40 -177.29(19) . . . . ?
F7 C51 C50 F8 -0.3(3) . . . . ?
F7 C51 C50 C49 179.89(19) . . . . ?
F7 C51 C52 C55 1.8(3) . . . . ?
F7 C51 C52 C53 -178.89(18) . . . . ?
F5 C54 C53 F6 -0.4(3) . . . . ?
F5 C54 C53 C52 -178.16(19) . . . . ?
O5 C24 C23 C22 -179.7(2) . . . . ?
O5 C30 C29 C28 -179.52(19) . . . . ?
O6 C26 C25 N2 0.1(3) . . . . ?
O6 C26 C25 C30 178.74(19) . . . . ?
O6 C26 C27 C28 -178.47(19) . . . . ?
O6 C36 C35 C34 177.9(2) . . . . ?
O4 C20 C21 C22 178.7(2) . . . . ?
O4 C32 C31 N2 1.8(3) . . . . ?
O4 C32 C31 C36 -179.0(2) . . . . ?
O4 C32 C33 C34 177.8(2) . . . . ?
O2 C8 C9 C10 177.89(19) . . . . ?
O2 C2 C1 N1 -2.0(3) . . . . ?
O2 C2 C1 C6 178.5(2) . . . . ?
O2 C2 C3 C4 -179.2(2) . . . . ?
O3 C12 C11 C10 179.2(2) . . . . ?
O3 C18 C17 C16 178.9(2) . . . . ?
O1 C14 C15 C16 177.7(2) . . . . ?
O1 C6 C5 C4 179.2(2) . . . . ?
N2 C19 C20 O4 2.0(3) . . . . ?
N2 C19 C20 C21 -178.7(2) . . . . ?
N2 C19 C24 O5 -0.9(3) . . . . ?
N2 C19 C24 C23 178.6(2) . . . . ?
N2 C25 C30 O5 -1.3(3) . . . . ?
N2 C25 C30 C29 178.3(2) . . . . ?
N2 C31 C36 O6 1.1(3) . . . . ?
N2 C31 C36 C35 -179.6(2) . . . . ?
N1 C7 C8 O2 0.5(3) . . . . ?
N1 C7 C8 C9 179.9(2) . . . . ?
N1 C7 C12 O3 1.6(3) . . . . ?
N1 C7 C12 C11 -179.0(2) . . . . ?
N1 C1 C6 O1 2.4(3) . . . . ?
N1 C1 C6 C5 -178.1(2) . . . . ?
N1 C13 C14 O1 2.8(3) . . . . ?
N1 C13 C14 C15 -178.0(2) . . . . ?
N1 C13 C18 O3 -0.8(3) . . . . ?
N1 C13 C18 C17 179.4(2) . . . . ?
C37 C38 C39 F3 178.01(19) . . . . ?
C37 C38 C39 C40 0.8(3) . . . . ?
C26 O6 C36 C31 -1.4(3) . . . . ?
C26 O6 C36 C35 179.3(2) . . . . ?
C26 C25 C30 O5 180.00(19) . . . . ?
C26 C25 C30 C29 -0.4(3) . . . . ?
C26 C27 C28 C29 -0.2(3) . . . . ?
C19 N2 C25 C26 -179.88(19) . . . . ?
C19 N2 C25 C30 1.4(3) . . . . ?
C19 N2 C31 C32 -1.5(3) . . . . ?
C19 N2 C31 C36 179.3(2) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C19 C24 C23 C22 0.8(3) . . . . ?
C43 C40 C41 F2 3.7(3) . . . . ?
C43 C40 C41 C42 -178.0(2) . . . . ?
C20 O4 C32 C31 -0.2(3) . . . . ?
C20 O4 C32 C33 -179.5(2) . . . . ?
C20 C19 C24 O5 179.66(19) . . . . ?
C20 C19 C24 C23 -0.9(3) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C25 N2 C19 C20 179.1(2) . . . . ?
C25 N2 C19 C24 -0.4(3) . . . . ?
C25 N2 C31 C32 179.0(2) . . . . ?
C25 N2 C31 C36 -0.1(3) . . . . ?
C25 C26 C27 C28 0.6(3) . . . . ?
C25 C30 C29 C28 0.9(3) . . . . ?
C38 C37 C46 C47 175.2(2) . . . . ?
C38 C37 C46 C48 -14.7(3) . . . . ?
C38 C37 C42 F1 177.37(18) . . . . ?
C38 C37 C42 C41 -0.5(3) . . . . ?
C38 C39 C40 C43 177.8(2) . . . . ?
C38 C39 C40 C41 -1.7(3) . . . . ?
C51 C52 C53 F6 -178.03(18) . . . . ?
C51 C52 C53 C54 -0.2(3) . . . . ?
C56 C55 C52 C51 4.4(3) . . . . ?
C56 C55 C52 C53 -174.8(2) . . . . ?
C39 C40 C41 F2 -176.77(18) . . . . ?
C39 C40 C41 C42 1.5(3) . . . . ?
C44 C43 C40 C39 12.3(3) . . . . ?
C44 C43 C40 C41 -168.3(2) . . . . ?
C40 C41 C42 F1 -178.38(19) . . . . ?
C40 C41 C42 C37 -0.4(3) . . . . ?
C55 C52 C53 F6 1.3(3) . . . . ?
C55 C52 C53 C54 179.1(2) . . . . ?
C49 C54 C53 F6 176.60(19) . . . . ?
C49 C54 C53 C52 -1.2(3) . . . . ?
C46 C37 C38 F4 -1.9(3) . . . . ?
C46 C37 C38 C39 -179.9(2) . . . . ?
C46 C37 C42 F1 -2.3(3) . . . . ?
C46 C37 C42 C41 179.8(2) . . . . ?
C58 C49 C54 F5 -0.5(3) . . . . ?
C58 C49 C54 C53 -177.4(2) . . . . ?
C58 C49 C50 F8 -2.0(3) . . . . ?
C58 C49 C50 C51 177.8(2) . . . . ?
C32 O4 C20 C19 -1.7(3) . . . . ?
C32 O4 C20 C21 179.0(2) . . . . ?
C32 C31 C36 O6 -178.1(2) . . . . ?
C32 C31 C36 C35 1.2(3) . . . . ?
C32 C33 C34 C35 1.3(4) . . . . ?
C24 O5 C30 C25 0.1(3) . . . . ?
C24 O5 C30 C29 -179.48(19) . . . . ?
C24 C19 C20 O4 -178.52(19) . . . . ?
C24 C19 C20 C21 0.7(3) . . . . ?
C24 C23 C22 C21 -0.6(4) . . . . ?
C30 O5 C24 C19 1.0(3) . . . . ?
C30 O5 C24 C23 -178.48(19) . . . . ?
C30 C29 C28 C27 -0.6(3) . . . . ?
C54 C49 C58 C59 -9.0(3) . . . . ?
C54 C49 C58 C60 173.5(2) . . . . ?
C54 C49 C50 F8 178.55(18) . . . . ?
C54 C49 C50 C51 -1.6(3) . . . . ?
C45 C43 C40 C39 -174.6(2) . . . . ?
C45 C43 C40 C41 4.8(3) . . . . ?
C50 C51 C52 C55 -178.6(2) . . . . ?
C50 C51 C52 C53 0.7(3) . . . . ?
C50 C49 C58 C59 171.6(2) . . . . ?
C50 C49 C58 C60 -5.9(3) . . . . ?
C50 C49 C54 F5 178.97(18) . . . . ?
C50 C49 C54 C53 2.0(3) . . . . ?
C31 N2 C19 C20 -0.4(3) . . . . ?
C31 N2 C19 C24 -179.9(2) . . . . ?
C31 N2 C25 C26 -0.4(3) . . . . ?
C31 N2 C25 C30 -179.08(19) . . . . ?
C31 C32 C33 C34 -1.5(3) . . . . ?
C31 C36 C35 C34 -1.5(3) . . . . ?
C52 C51 C50 F8 -179.84(19) . . . . ?
C52 C51 C50 C49 0.3(3) . . . . ?
C7 N1 C1 C2 -1.5(3) . . . . ?
C7 N1 C1 C6 178.0(2) . . . . ?
C7 N1 C13 C14 179.4(2) . . . . ?
C7 N1 C13 C18 0.8(3) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C7 C12 C11 C10 -0.2(3) . . . . ?
C36 O6 C26 C25 0.8(3) . . . . ?
C36 O6 C26 C27 179.9(2) . . . . ?
C36 C35 C34 C33 0.2(4) . . . . ?
C8 O2 C2 C1 4.7(3) . . . . ?
C8 O2 C2 C3 -175.04(19) . . . . ?
C8 C7 C12 O3 -179.8(2) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C2 O2 C8 C7 -3.9(3) . . . . ?
C2 O2 C8 C9 176.7(2) . . . . ?
C2 C1 C6 O1 -178.0(2) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C42 C37 C38 F4 178.45(18) . . . . ?
C42 C37 C38 C39 0.4(3) . . . . ?
C42 C37 C46 C47 -5.2(3) . . . . ?
C42 C37 C46 C48 165.0(2) . . . . ?
C1 N1 C7 C8 2.3(3) . . . . ?
C1 N1 C7 C12 -179.1(2) . . . . ?
C1 N1 C13 C14 -2.7(3) . . . . ?
C1 N1 C13 C18 178.7(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C1 C6 C5 C4 -0.3(4) . . . . ?
C27 C26 C25 N2 -179.0(2) . . . . ?
C27 C26 C25 C30 -0.4(3) . . . . ?
C57 C55 C52 C51 -167.1(2) . . . . ?
C57 C55 C52 C53 13.7(3) . . . . ?
C13 N1 C7 C8 -179.9(2) . . . . ?
C13 N1 C7 C12 -1.3(3) . . . . ?
C13 N1 C1 C2 -179.4(2) . . . . ?
C13 N1 C1 C6 0.2(3) . . . . ?
C13 C14 C15 C16 -1.5(4) . . . . ?
C13 C18 C17 C16 -1.2(4) . . . . ?
C3 C2 C1 N1 177.7(2) . . . . ?
C3 C2 C1 C6 -1.8(3) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C12 O3 C18 C13 1.1(3) . . . . ?
C12 O3 C18 C17 -179.1(2) . . . . ?
C12 C7 C8 O2 -178.1(2) . . . . ?
C12 C7 C8 C9 1.3(3) . . . . ?
C33 C32 C31 N2 -178.9(2) . . . . ?
C33 C32 C31 C36 0.3(3) . . . . ?
C14 O1 C6 C1 -2.4(3) . . . . ?
C14 O1 C6 C5 178.2(2) . . . . ?
C14 C13 C18 O3 -179.3(2) . . . . ?
C14 C13 C18 C17 0.9(4) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C6 O1 C14 C13 -0.3(3) . . . . ?
C6 O1 C14 C15 -179.4(2) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C18 O3 C12 C7 -1.5(3) . . . . ?
C18 O3 C12 C11 179.1(2) . . . . ?
C18 C13 C14 O1 -178.7(2) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C18 C17 C16 C15 0.3(4) . . . . ?
