#------------------------------------------------------------------------------
#$Date: 2025-10-06 09:59:33 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302546 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/51/1575176.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_1575176
loop_
_publ_author_name
'McDonald, Peter W.'
'Goerigk, Lars'
'Ritchie, Chris'
_publ_section_title
;
 Planarisation or a twist? Using steric engineering to unlock the origin
 of mechanofluorochromic red-shifts.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              15320
_journal_page_last               15332
_journal_paper_doi               10.1039/d5sc04257g
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         '3(C22 H12 F4 N2 O2)'
_chemical_formula_sum            'C66 H36 F12 N6 O6'
_chemical_formula_weight         1237.01
_chemical_name_systematic
2-(4-(9H-carbazol-9-yl)pyridin-1-ium-1-yl)-4,4,5,5-tetrafluoro-3-oxocyclopent-1-en-1-olate
_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     dual
_audit_creation_date             2025-05-25
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-06-06 deposited with the CCDC.	2025-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                89.004(2)
_cell_angle_beta                 81.638(2)
_cell_angle_gamma                89.699(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0644(2)
_cell_length_b                   15.0753(4)
_cell_length_c                   16.1709(4)
_cell_measurement_reflns_used    16060
_cell_measurement_temperature    292.45(10)
_cell_measurement_theta_max      79.0570
_cell_measurement_theta_min      3.9940
_cell_volume                     2668.20(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.45(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00 -52.00   0.50    1.02    --  -47.91-163.00  46.00   78
  2  ω    -79.00  -6.00   0.50    1.02    --  -47.91 116.00 -76.00  146
  3  ω   -112.00 -81.00   0.50    1.02    --  -47.91 163.00  72.00   62
  4  ω     40.00  88.00   0.50    1.02    --   47.91-116.00-164.00   96
  5  ω     93.00 118.00   0.50    1.02    --   47.91 163.00  72.00   50
  6  ω     73.00  98.00   0.50    1.02    --   47.91-163.00  46.00   50
  7  ω   -118.00 -93.00   0.50    4.07    --  -91.75-163.00  46.00   50
  8  ω   -131.00-106.00   0.50    4.07    --  -91.75-116.00-164.00   50
  9  ω    -96.00 -71.00   0.50    4.07    --  -91.75 163.00  72.00   50
 10  ω    -77.00 -52.00   0.50    4.07    --  -91.75 116.00 -76.00   50
 11  ω     89.00 114.00   0.50    4.07    --  113.25 163.00  72.00   50
 12  ω     93.00 119.00   0.50    4.07    --  113.25-163.00  46.00   52
 13  ω     56.00 103.00   0.50    4.07    --  113.25-116.00-164.00   94
 14  ω    111.00 141.00   0.50    4.07    --  113.25 116.00 -76.00   60
 15  ω    -63.00  23.00   0.50    1.02    --  -47.91  57.00  90.00  172
 16  ω    -56.00  28.00   0.50    1.02    --  -47.91  19.00-150.00  168
 17  ω    -19.00  29.00   0.50    1.02    --   47.91 -19.00 -60.00   96
 18  ω     34.00  61.00   0.50    1.02    --   47.91 -19.00 -60.00   54
 19  ω     36.00  80.00   0.50    1.02    --   47.91  37.00 -60.00   88
 20  ω    -46.00 -20.00   0.50    4.07    --  -91.75  45.00 -30.00   52
 21  ω   -144.00 -75.00   0.50    4.07    --  -91.75 -61.00 -90.00  138
 22  ω     39.00  66.00   0.50    4.07    --  113.25 -30.00 120.00   54
 23  ω     39.00  64.00   0.50    4.07    --  113.25 -30.00-180.00   50
 24  ω     43.00  76.00   0.50    4.07    --  113.25 -45.00 150.00   66
 25  ω     39.00  66.00   0.50    4.07    --  113.25 -30.00  30.00   54
 26  ω     42.00 106.00   0.50    4.07    --  113.25 -94.00-180.00  128
 27  ω     39.00  66.00   0.50    4.07    --  113.25 -30.00   0.00   54
 28  ω     52.00 104.00   0.50    4.07    --  113.25 -94.00   0.00  104
 29  ω     39.00  65.00   0.50    4.07    --  113.25 -30.00 -30.00   52
 30  ω     46.00  75.00   0.50    4.07    --  113.25 -45.00-150.00   58
 31  ω     39.00  66.00   0.50    4.07    --  113.25 -30.00  60.00   54
 32  ω    146.00 172.00   0.50    4.07    --  113.25 125.00-120.00   52
 33  ω     51.00  89.00   0.50    4.07    --  113.25 -15.00 120.00   76
 34  ω     94.00 125.00   0.50    4.07    --  113.25 -15.00 120.00   62
 35  ω    105.00 130.00   0.50    4.07    --  113.25 125.00  30.00   50
 36  ω    133.00 162.00   0.50    4.07    --  113.25 125.00  30.00   58
 37  ω     40.00  65.00   0.50    4.07    --  113.25 -30.00 -90.00   50
 38  ω     39.00  65.00   0.50    4.07    --  113.25 -30.00  90.00   52
 39  ω     95.00 123.00   0.50    4.07    --  113.25 125.00-120.00   56
 40  ω     46.00  75.00   0.50    4.07    --  113.25 -45.00   0.00   58
 41  ω     53.00 106.00   0.50    4.07    --  113.25 -94.00 -60.00  106
 42  ω     70.00 101.00   0.50    4.07    --  113.25 -94.00  30.00   62
 43  ω     46.00  71.00   0.50    4.07    --  113.25 -45.00 -60.00   50
 44  ω     60.00 104.00   0.50    4.07    --  113.25 -94.00  90.00   88
 45  ω     40.00  65.00   0.50    4.07    --  113.25 -30.00 150.00   50
 46  ω     45.00  70.00   0.50    4.07    --  113.25 -94.00 -30.00   50
 47  ω     44.00  71.00   0.50    4.07    --  113.25 -45.00-180.00   54
 48  ω     42.00  76.00   0.50    4.07    --  113.25 -45.00  60.00   68
 49  ω     79.00 106.00   0.50    4.07    --  113.25 -94.00 -30.00   54
 50  ω    128.00 175.00   0.50    4.07    --  113.25  30.00 -60.00   94
 51  ω     69.00 104.00   0.50    4.07    --  113.25 -94.00-150.00   70
 52  ω     46.00  74.00   0.50    4.07    --  113.25 -45.00  90.00   56
 53  ω     73.00 118.00   0.50    4.07    --  113.25 -15.00 -60.00   90
 54  ω     47.00  72.00   0.50    4.07    --  113.25 -61.00 150.00   50
 55  ω     96.00 128.00   0.50    4.07    --  113.25 -61.00 150.00   64
 56  ω     78.00 103.00   0.50    4.07    --  113.25 -94.00 120.00   50
 57  ω     62.00  99.00   0.50    4.07    --  113.25 -94.00  60.00   74
 58  ω     71.00 106.00   0.50    4.07    --  113.25 -94.00-120.00   70
 59  ω    115.00 171.00   0.50    4.07    --  113.25  15.00-180.00  112
 60  ω     41.00  66.00   0.50    4.07    --  113.25 -30.00 -60.00   50
 61  ω     93.00 119.00   0.50    4.07    --  113.25  77.00  60.00   52
 62  ω    133.00 177.00   0.50    4.07    --  113.25  77.00  60.00   88
 63  ω     72.00  97.00   0.50    4.07    --  113.25 -94.00 -90.00   50
 64  ω     43.00  72.00   0.50    4.07    --  113.25 -45.00 -30.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0007054000
_diffrn_orient_matrix_UB_12      0.0871792000
_diffrn_orient_matrix_UB_13      0.0483832000
_diffrn_orient_matrix_UB_21      -0.0491086000
_diffrn_orient_matrix_UB_22      -0.0500483000
_diffrn_orient_matrix_UB_23      0.0817628000
_diffrn_orient_matrix_UB_31      0.1318852000
_diffrn_orient_matrix_UB_32      -0.0184708000
_diffrn_orient_matrix_UB_33      0.0157658000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40925
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.066
_diffrn_reflns_theta_min         3.996
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1260
_exptl_crystal_preparation       oil
_exptl_crystal_recrystallization_method acetone
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     858
_refine_ls_number_reflns         11375
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0488
_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)+(0.0461P)²+1.0525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9072
_reflns_number_total             11375
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc04257g2.cif
_cod_data_source_block           pm3_36_292k_acetone_auto
_cod_depositor_comments
'Adding full bibliography for 1575172--1575185.cif.'
_cod_database_code               1575176
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C22H12F4N2O2
_chemical_oxdiff_usercomment     'Yellow irregular block at 292.5 K'
_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   0.957
_shelx_estimated_absorpt_t_min   0.843
_diffrn_oxdiff_digest_hkl
;
01b7770302eb39196049a2d7fe20a150e2cfd2
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F1-C21 \\sim F1A-C21
 with sigma of 0.02
 C21-F4 \\sim C21-F4A
 with sigma of 0.02
 F3-C21 \\sim F3A-C21
 with sigma of 0.04
 F3-C20 \\sim F3A-C20A
 with sigma of 0.02
 F2-C19 \\sim F2A-C19
 with sigma of 0.04
 F2-C20 \\sim F2A-C20A
 with sigma of 0.02
 F3-C19 \\sim F3A-C19
 with sigma of 0.04
 C19-C20 \\sim C19-C20A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21
 with sigma of 0.02
 F2-C21 \\sim F2A-C21
 with sigma of 0.04
 F3-F2 \\sim F3A-F2A
 with sigma of 0.04
3. Others
 Sof(F1A)=Sof(F4A)=1-FVAR(1)
 Sof(F1)=Sof(F4)=FVAR(1)
 Sof(F3A)=Sof(C20A)=Sof(F2A)=1-FVAR(2)
 Sof(F3)=Sof(F2)=Sof(C20)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C37(H37), C61(H61), C36(H36), C59(H59), C60(H60), C38(H38), C16(H16),
 C15(H15), C39(H39), C58(H58), C14(H14), C17(H17), C33(H33), C24(H24), C49(H49),
  C55(H55), C46(H46), C11(H11), C2(H2), C27(H27), C30(H30), C52(H52), C26(H26),
 C54(H54), C48(H48), C25(H25), C8(H8), C32(H32), C5(H5), C47(H47), C31(H31),
 C53(H53), C10(H10), C3(H3), C9(H9), C4(H4)
;
_olex2_exptl_crystal_mounting_method oil
_olex2_submission_original_sample_id '4a 292 K'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.727
_oxdiff_exptl_absorpt_empirical_full_min 0.547
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
F12 F 0.10932(14) 0.36651(9) 0.23236(9) 0.0755(4) Uani 1 1 d . . . . .
F9 F -0.06958(15) 0.38403(10) 0.19710(9) 0.0777(4) Uani 1 1 d . . . . .
N4 N 0.75519(14) 0.30934(10) 0.05595(9) 0.0413(3) Uani 1 1 d . . . . .
F7 F 0.86649(16) 0.02683(10) 0.11085(10) 0.0876(5) Uani 1 1 d . . . . .
O3 O 0.79514(16) 0.19894(11) -0.10123(8) 0.0656(4) Uani 1 1 d . . . . .
N2 N 0.45345(13) 0.04665(10) 0.30833(8) 0.0405(3) Uani 1 1 d . . . . .
O1 O 0.44646(17) 0.20996(10) 0.19686(8) 0.0676(4) Uani 1 1 d . . . . .
N6 N 0.02025(14) 0.63864(10) 0.33821(9) 0.0418(3) Uani 1 1 d . . . . .
N3 N 0.77276(14) 0.57608(10) 0.11278(9) 0.0435(3) Uani 1 1 d . . . . .
F6 F 0.67316(18) 0.01234(11) 0.12071(11) 0.1000(6) Uani 1 1 d . . . . .
F8 F 0.88175(19) 0.03307(11) -0.04366(11) 0.0994(6) Uani 1 1 d . . . . .
N5 N 0.11731(15) 0.89359(10) 0.39816(9) 0.0460(3) Uani 1 1 d . . . . .
O2 O 0.46670(19) 0.12667(11) 0.47770(9) 0.0739(5) Uani 1 1 d . . . . .
N1 N 0.44619(15) -0.21877(11) 0.24153(10) 0.0481(4) Uani 1 1 d . . . . .
O6 O -0.10879(19) 0.49642(11) 0.45342(10) 0.0793(5) Uani 1 1 d . . . . .
O5 O 0.0673(2) 0.54285(11) 0.17234(9) 0.0774(5) Uani 1 1 d . . . . .
F5 F 0.6860(2) 0.03103(12) -0.03671(12) 0.1133(7) Uani 1 1 d . . . . .
O4 O 0.7340(2) 0.17533(12) 0.19359(9) 0.0779(5) Uani 1 1 d . . . . .
F3 F 0.5095(7) 0.3583(3) 0.2867(4) 0.0798(16) Uani 0.61(2) 1 d D . P A 1
F11 F 0.0149(2) 0.34066(11) 0.38134(10) 0.1155(8) Uani 1 1 d . . . . .
F10 F -0.1655(2) 0.36083(14) 0.34711(12) 0.1194(8) Uani 1 1 d . . . . .
C13 C 0.44822(16) -0.13072(12) 0.26497(11) 0.0432(4) Uani 1 1 d . . . . .
C35 C 0.76175(16) 0.48938(12) 0.08880(10) 0.0406(4) Uani 1 1 d . . . . .
C18 C 0.45596(17) 0.13789(12) 0.33016(10) 0.0435(4) Uani 1 1 d . . . . .
F2 F 0.3237(4) 0.3258(4) 0.3271(6) 0.0915(19) Uani 0.61(2) 1 d D . P A 1
C23 C 0.82248(17) 0.64795(12) 0.06120(11) 0.0438(4) Uani 1 1 d . . . . .
C34 C 0.74707(17) 0.60763(13) 0.19644(11) 0.0445(4) Uani 1 1 d . . . . .
C37 C 0.67168(17) 0.34549(12) 0.11564(11) 0.0442(4) Uani 1 1 d . . . . .
H37 H 0.612748 0.309276 0.145943 0.053 Uiso 1 1 calc R U . . .
C61 C 0.10950(17) 0.77819(12) 0.29529(11) 0.0449(4) Uani 1 1 d . . . . .
H61 H 0.149166 0.814629 0.252970 0.054 Uiso 1 1 calc R U . . .
C62 C -0.00163(17) 0.54838(12) 0.32072(11) 0.0437(4) Uani 1 1 d . . . . .
C36 C 0.67224(17) 0.43358(12) 0.13216(11) 0.0436(4) Uani 1 1 d . . . . .
H36 H 0.612787 0.457027 0.172550 0.052 Uiso 1 1 calc R U . . .
C40 C 0.75974(17) 0.21529(12) 0.04788(11) 0.0424(4) Uani 1 1 d . . . . .
C59 C -0.01193(18) 0.67002(13) 0.41670(11) 0.0479(4) Uani 1 1 d . . . . .
H59 H -0.054072 0.633270 0.457749 0.057 Uiso 1 1 calc R U . . .
C60 C 0.07924(17) 0.69385(12) 0.27783(11) 0.0443(4) Uani 1 1 d . . . . .
H60 H 0.099178 0.673391 0.223612 0.053 Uiso 1 1 calc R U . . .
C57 C 0.08136(17) 0.81046(12) 0.37648(11) 0.0429(4) Uani 1 1 d . . . . .
C38 C 0.83483(17) 0.36303(12) 0.00721(11) 0.0443(4) Uani 1 1 d . . . . .
H38 H 0.887551 0.339072 -0.036881 0.053 Uiso 1 1 calc R U . . .
C16 C 0.48624(18) -0.01816(13) 0.36028(11) 0.0463(4) Uani 1 1 d . . . . .
H16 H 0.510774 -0.002541 0.410677 0.056 Uiso 1 1 calc R U . . .
C45 C 0.11699(17) 0.97249(12) 0.34939(12) 0.0457(4) Uani 1 1 d . . . . .
C41 C 0.77872(18) 0.17130(13) -0.02845(11) 0.0468(4) Uani 1 1 d . . . . .
C44 C 0.74957(19) 0.15869(13) 0.11933(12) 0.0498(4) Uani 1 1 d . . . . .
C28 C 0.83005(18) 0.72184(13) 0.11150(12) 0.0482(4) Uani 1 1 d . . . . .
C15 C 0.41527(18) 0.02297(13) 0.23549(11) 0.0463(4) Uani 1 1 d . . . . .
H15 H 0.390883 0.066790 0.200188 0.056 Uiso 1 1 calc R U . . .
C39 C 0.83878(17) 0.45192(12) 0.02192(11) 0.0447(4) Uani 1 1 d . . . . .
H39 H 0.893119 0.487868 -0.012791 0.054 Uiso 1 1 calc R U . . .
C56 C 0.14849(17) 0.91630(13) 0.47705(11) 0.0466(4) Uani 1 1 d . . . . .
C50 C 0.14715(17) 1.04329(13) 0.39740(12) 0.0485(4) Uani 1 1 d . . . . .
C12 C 0.47336(18) -0.24934(14) 0.15864(12) 0.0491(4) Uani 1 1 d . . . . .
C58 C 0.01624(18) 0.75398(13) 0.43639(11) 0.0473(4) Uani 1 1 d . . . . .
H58 H -0.008061 0.774113 0.490309 0.057 Uiso 1 1 calc R U . . .
C29 C 0.78128(18) 0.69652(13) 0.19608(12) 0.0485(4) Uani 1 1 d . . . . .
C14 C 0.41210(18) -0.06352(13) 0.21338(11) 0.0471(4) Uani 1 1 d . . . . .
H14 H 0.385561 -0.078005 0.163331 0.057 Uiso 1 1 calc R U . . .
C1 C 0.40103(18) -0.29114(13) 0.29359(13) 0.0492(4) Uani 1 1 d . . . . .
C51 C 0.16610(17) 1.00811(14) 0.47818(12) 0.0490(4) Uani 1 1 d . . . . .
C17 C 0.48398(18) -0.10554(13) 0.34017(11) 0.0480(4) Uani 1 1 d . . . . .
H17 H 0.506475 -0.148592 0.376947 0.058 Uiso 1 1 calc R U . . .
C19 C 0.44966(19) 0.20837(13) 0.27213(11) 0.0497(4) Uani 1 1 d D . . . .
C64 C 0.0031(2) 0.41147(14) 0.25108(12) 0.0530(5) Uani 1 1 d . . . . .
C22 C 0.4616(2) 0.16704(14) 0.41170(11) 0.0516(5) Uani 1 1 d . . . . .
C6 C 0.39591(19) -0.36551(14) 0.24323(14) 0.0542(5) Uani 1 1 d . . . . .
C63 C 0.0280(2) 0.51049(13) 0.24149(11) 0.0508(4) Uani 1 1 d . . . . .
C66 C -0.0595(2) 0.48728(14) 0.38150(12) 0.0531(5) Uani 1 1 d . . . . .
C7 C 0.44361(19) -0.33934(14) 0.15832(14) 0.0546(5) Uani 1 1 d . . . . .
C33 C 0.70170(19) 0.56414(16) 0.27106(12) 0.0548(5) Uani 1 1 d . . . . .
H33 H 0.682695 0.504063 0.272356 0.066 Uiso 1 1 calc R U . . .
C42 C 0.7777(2) 0.07180(14) -0.00754(13) 0.0562(5) Uani 1 1 d . . . . .
C24 C 0.8514(2) 0.65482(13) -0.02501(12) 0.0537(5) Uani 1 1 d . . . . .
H24 H 0.842686 0.606899 -0.059090 0.064 Uiso 1 1 calc R U . . .
C49 C 0.1516(2) 1.12922(14) 0.36381(15) 0.0598(5) Uani 1 1 d . . . . .
H49 H 0.171319 1.176879 0.395033 0.072 Uiso 1 1 calc R U . . .
C55 C 0.1692(2) 0.86161(16) 0.54399(13) 0.0569(5) Uani 1 1 d . . . . .
H55 H 0.162254 0.800285 0.541603 0.068 Uiso 1 1 calc R U . . .
C46 C 0.0879(2) 0.98553(15) 0.26939(13) 0.0562(5) Uani 1 1 d . . . . .
H46 H 0.065691 0.938550 0.238316 0.067 Uiso 1 1 calc R U . . .
C11 C 0.5294(2) -0.20499(17) 0.08731(13) 0.0592(5) Uani 1 1 d . . . . .
H11 H 0.550638 -0.145468 0.088511 0.071 Uiso 1 1 calc R U . . .
C43 C 0.7648(2) 0.06424(13) 0.08738(13) 0.0543(5) Uani 1 1 d . . . . .
C2 C 0.3595(2) -0.29436(15) 0.37883(14) 0.0577(5) Uani 1 1 d . . . . .
H2 H 0.362534 -0.244750 0.411853 0.069 Uiso 1 1 calc R U . . .
C27 C 0.8734(2) 0.80253(14) 0.07657(15) 0.0611(5) Uani 1 1 d . . . . .
H27 H 0.880123 0.851200 0.110144 0.073 Uiso 1 1 calc R U . . .
C30 C 0.7645(2) 0.74445(16) 0.26987(14) 0.0615(5) Uani 1 1 d . . . . .
H30 H 0.786403 0.803941 0.269539 0.074 Uiso 1 1 calc R U . . .
C20 C 0.4360(9) 0.2929(5) 0.3232(5) 0.065(3) Uani 0.61(2) 1 d D . P A 1
C52 C 0.1977(2) 1.04679(17) 0.54964(14) 0.0627(6) Uani 1 1 d . . . . .
H52 H 0.208890 1.107780 0.551553 0.075 Uiso 1 1 calc R U . . .
C26 C 0.9061(2) 0.80886(14) -0.00844(15) 0.0660(6) Uani 1 1 d . . . . .
H26 H 0.936615 0.862038 -0.032790 0.079 Uiso 1 1 calc R U . . .
C54 C 0.2003(2) 0.9019(2) 0.61408(14) 0.0668(6) Uani 1 1 d . . . . .
H54 H 0.213514 0.867014 0.659923 0.080 Uiso 1 1 calc R U . . .
C65 C -0.0539(3) 0.39657(15) 0.34126(14) 0.0646(6) Uani 1 1 d . . . . .
C48 C 0.1264(2) 1.14222(15) 0.28366(16) 0.0693(6) Uani 1 1 d . . . . .
H48 H 0.131452 1.198957 0.259925 0.083 Uiso 1 1 calc R U . . .
C25 C 0.8939(2) 0.73640(15) -0.05837(14) 0.0638(6) Uani 1 1 d . . . . .
H25 H 0.914922 0.742601 -0.115986 0.077 Uiso 1 1 calc R U . . .
C8 C 0.4678(2) -0.38580(17) 0.08357(17) 0.0699(7) Uani 1 1 d . . . . .
H8 H 0.447294 -0.445415 0.081761 0.084 Uiso 1 1 calc R U . . .
C32 C 0.6859(2) 0.61343(19) 0.34327(13) 0.0646(6) Uani 1 1 d . . . . .
H32 H 0.654486 0.585794 0.393628 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3485(2) -0.44496(15) 0.27933(19) 0.0701(6) Uani 1 1 d . . . . .
H5 H 0.344260 -0.494735 0.246715 0.084 Uiso 1 1 calc R U . . .
C47 C 0.0936(2) 1.07175(16) 0.23796(15) 0.0671(6) Uani 1 1 d . . . . .
H47 H 0.074828 1.082599 0.184479 0.080 Uiso 1 1 calc R U . . .
C31 C 0.7153(2) 0.70266(18) 0.34287(14) 0.0672(6) Uani 1 1 d . . . . .
H31 H 0.701648 0.734259 0.392254 0.081 Uiso 1 1 calc R U . . .
C53 C 0.2122(2) 0.9932(2) 0.61745(15) 0.0699(7) Uani 1 1 d . . . . .
H53 H 0.230164 1.018689 0.666174 0.084 Uiso 1 1 calc R U . . .
C10 C 0.5524(2) -0.2530(2) 0.01424(15) 0.0705(7) Uani 1 1 d . . . . .
H10 H 0.588820 -0.224892 -0.034681 0.085 Uiso 1 1 calc R U . . .
C3 C 0.3135(2) -0.37429(17) 0.41271(17) 0.0705(6) Uani 1 1 d . . . . .
H3 H 0.285359 -0.378357 0.469704 0.085 Uiso 1 1 calc R U . . .
C9 C 0.5224(2) -0.3417(2) 0.01273(16) 0.0759(8) Uani 1 1 d . . . . .
H9 H 0.539405 -0.372308 -0.037100 0.091 Uiso 1 1 calc R U . . .
C4 C 0.3082(2) -0.44867(17) 0.3638(2) 0.0761(7) Uani 1 1 d . . . . .
H4 H 0.277099 -0.501527 0.388482 0.091 Uiso 1 1 calc R U . . .
F1 F 0.3302(10) 0.2892(4) 0.4527(4) 0.096(2) Uani 0.519(18) 1 d D . P A 1
C21 C 0.4584(3) 0.26774(16) 0.40828(14) 0.0776(8) Uani 1 1 d D . . . .
F4 F 0.5207(13) 0.3097(3) 0.4500(5) 0.104(4) Uani 0.519(18) 1 d D . P A 1
F1A F 0.4064(15) 0.3066(3) 0.4708(3) 0.105(4) Uani 0.481(18) 1 d D . P A 2
F4A F 0.5926(9) 0.2932(4) 0.4098(7) 0.095(3) Uani 0.481(18) 1 d D . P A 2
F3A F 0.560(3) 0.3384(13) 0.2942(8) 0.132(6) Uani 0.39(2) 1 d D . P A 2
C20A C 0.4540(17) 0.2961(7) 0.3189(6) 0.056(4) Uani 0.39(2) 1 d D . P A 2
F2A F 0.363(3) 0.3478(11) 0.3048(9) 0.142(6) Uani 0.39(2) 1 d 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 0.0181 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'
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
C37 N4 C40 119.06(14) . . ?
C38 N4 C37 119.33(15) . . ?
C38 N4 C40 121.57(15) . . ?
C16 N2 C18 120.98(15) . . ?
C16 N2 C15 118.79(16) . . ?
C15 N2 C18 120.22(15) . . ?
C59 N6 C62 120.30(14) . . ?
C59 N6 C60 118.88(16) . . ?
C60 N6 C62 120.74(15) . . ?
C35 N3 C23 126.62(15) . . ?
C35 N3 C34 125.68(15) . . ?
C23 N3 C34 107.44(15) . . ?
C57 N5 C45 126.30(15) . . ?
C57 N5 C56 125.49(15) . . ?
C45 N5 C56 107.89(16) . . ?
C13 N1 C12 125.22(16) . . ?
C13 N1 C1 126.09(16) . . ?
C1 N1 C12 108.16(16) . . ?
N1 C13 C14 120.40(16) . . ?
N1 C13 C17 122.32(16) . . ?
C17 C13 C14 117.27(17) . . ?
N3 C35 C36 120.70(16) . . ?
N3 C35 C39 122.79(16) . . ?
C39 C35 C36 116.50(16) . . ?
C19 C18 N2 123.19(16) . . ?
C22 C18 N2 123.71(16) . . ?
C22 C18 C19 113.07(17) . . ?
C28 C23 N3 108.55(16) . . ?
C24 C23 N3 130.39(18) . . ?
C24 C23 C28 120.82(17) . . ?
C29 C34 N3 108.33(16) . . ?
C33 C34 N3 131.10(19) . . ?
C33 C34 C29 120.51(18) . . ?
N4 C37 H37 119.3 . . ?
N4 C37 C36 121.38(16) . . ?
C36 C37 H37 119.3 . . ?
C60 C61 H61 119.8 . . ?
C60 C61 C57 120.48(16) . . ?
C57 C61 H61 119.8 . . ?
C63 C62 N6 124.14(16) . . ?
C63 C62 C66 112.56(17) . . ?
C66 C62 N6 123.28(16) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.53(17) . . ?
C37 C36 H36 119.7 . . ?
C41 C40 N4 124.44(15) . . ?
C41 C40 C44 114.57(17) . . ?
C44 C40 N4 120.94(16) . . ?
N6 C59 H59 119.3 . . ?
C58 C59 N6 121.36(16) . . ?
C58 C59 H59 119.3 . . ?
N6 C60 H60 119.3 . . ?
C61 C60 N6 121.41(16) . . ?
C61 C60 H60 119.3 . . ?
N5 C57 C61 122.38(16) . . ?
N5 C57 C58 120.61(16) . . ?
C58 C57 C61 117.00(17) . . ?
N4 C38 H38 119.5 . . ?
N4 C38 C39 120.95(16) . . ?
C39 C38 H38 119.5 . . ?
N2 C16 H16 119.3 . . ?
N2 C16 C17 121.49(16) . . ?
C17 C16 H16 119.3 . . ?
C50 C45 N5 108.25(16) . . ?
C46 C45 N5 129.91(18) . . ?
C46 C45 C50 121.78(18) . . ?
O3 C41 C40 131.92(19) . . ?
O3 C41 C42 121.44(18) . . ?
C40 C41 C42 106.64(16) . . ?
O4 C44 C40 131.01(19) . . ?
O4 C44 C43 122.42(18) . . ?
C40 C44 C43 106.57(16) . . ?
C23 C28 C29 107.68(17) . . ?
C27 C28 C23 120.73(19) . . ?
C27 C28 C29 131.5(2) . . ?
N2 C15 H15 119.4 . . ?
C14 C15 N2 121.27(17) . . ?
C14 C15 H15 119.4 . . ?
C35 C39 H39 119.7 . . ?
C38 C39 C35 120.63(16) . . ?
C38 C39 H39 119.7 . . ?
C51 C56 N5 108.68(16) . . ?
C55 C56 N5 129.69(19) . . ?
C55 C56 C51 121.48(19) . . ?
C45 C50 C51 107.92(17) . . ?
C49 C50 C45 119.68(19) . . ?
C49 C50 C51 132.4(2) . . ?
C7 C12 N1 108.49(18) . . ?
C11 C12 N1 129.3(2) . . ?
C11 C12 C7 121.98(19) . . ?
C59 C58 C57 120.76(17) . . ?
C59 C58 H58 119.6 . . ?
C57 C58 H58 119.6 . . ?
C34 C29 C28 107.99(17) . . ?
C34 C29 C30 120.44(19) . . ?
C30 C29 C28 131.6(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.70(17) . . ?
C15 C14 H14 119.6 . . ?
C6 C1 N1 108.22(18) . . ?
C2 C1 N1 130.02(19) . . ?
C2 C1 C6 121.7(2) . . ?
C56 C51 C50 107.25(17) . . ?
C52 C51 C56 119.5(2) . . ?
C52 C51 C50 133.2(2) . . ?
C13 C17 H17 119.8 . . ?
C16 C17 C13 120.44(17) . . ?
C16 C17 H17 119.8 . . ?
O1 C19 C18 132.36(19) . . ?
O1 C19 C20 121.5(3) . . ?
O1 C19 C20A 119.6(4) . . ?
C18 C19 C20 106.0(3) . . ?
C18 C19 C20A 108.0(4) . . ?
F12 C64 C63 109.22(18) . . ?
F12 C64 C65 112.01(18) . . ?
F9 C64 F12 106.04(17) . . ?
F9 C64 C63 111.55(16) . . ?
F9 C64 C65 112.23(19) . . ?
C65 C64 C63 105.85(16) . . ?
O2 C22 C18 132.1(2) . . ?
O2 C22 C21 121.05(18) . . ?
C18 C22 C21 106.85(17) . . ?
C1 C6 C7 107.57(19) . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C7 132.9(2) . . ?
O5 C63 C62 132.11(19) . . ?
O5 C63 C64 120.12(18) . . ?
C62 C63 C64 107.77(16) . . ?
O6 C66 C62 132.2(2) . . ?
O6 C66 C65 120.49(18) . . ?
C62 C66 C65 107.26(17) . . ?
C12 C7 C6 107.52(18) . . ?
C12 C7 C8 119.2(2) . . ?
C8 C7 C6 133.2(2) . . ?
C34 C33 H33 121.2 . . ?
C32 C33 C34 117.7(2) . . ?
C32 C33 H33 121.2 . . ?
F8 C42 C41 110.59(19) . . ?
F8 C42 C43 111.15(18) . . ?
F5 C42 F8 106.7(2) . . ?
F5 C42 C41 111.23(18) . . ?
F5 C42 C43 111.3(2) . . ?
C43 C42 C41 105.99(16) . . ?
C23 C24 H24 121.4 . . ?
C23 C24 C25 117.2(2) . . ?
C25 C24 H24 121.4 . . ?
C50 C49 H49 120.6 . . ?
C48 C49 C50 118.8(2) . . ?
C48 C49 H49 120.6 . . ?
C56 C55 H55 121.2 . . ?
C54 C55 C56 117.5(2) . . ?
C54 C55 H55 121.2 . . ?
C45 C46 H46 121.5 . . ?
C47 C46 C45 116.9(2) . . ?
C47 C46 H46 121.5 . . ?
C12 C11 H11 121.3 . . ?
C10 C11 C12 117.4(2) . . ?
C10 C11 H11 121.3 . . ?
F7 C43 C44 110.03(18) . . ?
F7 C43 C42 110.18(18) . . ?
F6 C43 F7 105.27(18) . . ?
F6 C43 C44 111.92(19) . . ?
F6 C43 C42 113.41(19) . . ?
C42 C43 C44 106.08(16) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C28 C27 H27 120.7 . . ?
C26 C27 C28 118.6(2) . . ?
C26 C27 H27 120.7 . . ?
C29 C30 H30 120.5 . . ?
C31 C30 C29 119.1(2) . . ?
C31 C30 H30 120.5 . . ?
F3 C20 C19 111.6(6) . . ?
F3 C20 C21 114.2(7) . . ?
F2 C20 F3 104.6(6) . . ?
F2 C20 C19 110.8(7) . . ?
F2 C20 C21 109.1(7) . . ?
C21 C20 C19 106.5(5) . . ?
C51 C52 H52 120.5 . . ?
C53 C52 C51 118.9(2) . . ?
C53 C52 H52 120.5 . . ?
C27 C26 H26 119.8 . . ?
C27 C26 C25 120.4(2) . . ?
C25 C26 H26 119.8 . . ?
C55 C54 H54 119.3 . . ?
C55 C54 C53 121.4(2) . . ?
C53 C54 H54 119.3 . . ?
F11 C65 C64 111.0(2) . . ?
F11 C65 C66 109.91(19) . . ?
F10 C65 F11 107.1(2) . . ?
F10 C65 C64 111.8(2) . . ?
F10 C65 C66 110.9(2) . . ?
C64 C65 C66 106.00(17) . . ?
C49 C48 H48 119.7 . . ?
C49 C48 C47 120.7(2) . . ?
C47 C48 H48 119.7 . . ?
C24 C25 H25 118.9 . . ?
C26 C25 C24 122.1(2) . . ?
C26 C25 H25 118.9 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C33 C32 H32 119.0 . . ?
C33 C32 C31 122.1(2) . . ?
C31 C32 H32 119.0 . . ?
C6 C5 H5 120.5 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.5 . . ?
C46 C47 H47 119.0 . . ?
C48 C47 C46 122.1(2) . . ?
C48 C47 H47 119.0 . . ?
C30 C31 C32 120.1(2) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C52 C53 C54 121.0(2) . . ?
C52 C53 H53 119.5 . . ?
C54 C53 H53 119.5 . . ?
C11 C10 H10 119.4 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10 119.4 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C22 C21 F1 102.8(3) . . ?
C22 C21 F4A 103.1(3) . . ?
C20 C21 C22 106.4(3) . . ?
C20 C21 F1 96.6(5) . . ?
F4 C21 C22 119.6(4) . . ?
F4 C21 C20 124.9(5) . . ?
F4 C21 F1 100.8(5) . . ?
F1A C21 C22 117.6(3) . . ?
F1A C21 F4A 101.4(5) . . ?
F1A C21 C20A 125.1(7) . . ?
C20A C21 C22 107.8(4) . . ?
C20A C21 F4A 96.5(8) . . ?
C21 C20A C19 104.3(6) . . ?
F3A C20A C19 110.7(9) . . ?
F3A C20A C21 105.2(9) . . ?
F2A C20A C19 110.2(8) . . ?
F2A C20A C21 117.1(9) . . ?
F2A C20A F3A 109.1(10) . . ?
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
F12 C64 1.352(3) . ?
F9 C64 1.341(2) . ?
N4 C37 1.355(2) . ?
N4 C40 1.426(2) . ?
N4 C38 1.355(2) . ?
F7 C43 1.356(3) . ?
O3 C41 1.230(2) . ?
N2 C18 1.427(2) . ?
N2 C16 1.359(2) . ?
N2 C15 1.362(2) . ?
O1 C19 1.223(2) . ?
N6 C62 1.424(2) . ?
N6 C59 1.360(2) . ?
N6 C60 1.365(2) . ?
N3 C35 1.381(2) . ?
N3 C23 1.419(2) . ?
N3 C34 1.430(2) . ?
F6 C43 1.328(3) . ?
F8 C42 1.348(3) . ?
N5 C57 1.383(2) . ?
N5 C45 1.416(2) . ?
N5 C56 1.417(2) . ?
O2 C22 1.228(2) . ?
N1 C13 1.388(2) . ?
N1 C12 1.415(2) . ?
N1 C1 1.414(3) . ?
O6 C66 1.220(2) . ?
O5 C63 1.233(2) . ?
F5 C42 1.336(3) . ?
O4 C44 1.218(2) . ?
F3 C20 1.353(9) . ?
F11 C65 1.351(3) . ?
F10 C65 1.340(3) . ?
C13 C14 1.395(3) . ?
C13 C17 1.392(3) . ?
C35 C36 1.402(2) . ?
C35 C39 1.401(2) . ?
C18 C19 1.413(3) . ?
C18 C22 1.407(3) . ?
F2 C20 1.328(9) . ?
C23 C28 1.401(3) . ?
C23 C24 1.386(3) . ?
C34 C29 1.394(3) . ?
C34 C33 1.392(3) . ?
C37 H37 0.9300 . ?
C37 C36 1.359(3) . ?
C61 H61 0.9300 . ?
C61 C60 1.361(3) . ?
C61 C57 1.400(3) . ?
C62 C63 1.406(3) . ?
C62 C66 1.420(3) . ?
C36 H36 0.9300 . ?
C40 C41 1.400(3) . ?
C40 C44 1.416(2) . ?
C59 H59 0.9300 . ?
C59 C58 1.359(3) . ?
C60 H60 0.9300 . ?
C57 C58 1.399(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.367(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.364(3) . ?
C45 C50 1.400(3) . ?
C45 C46 1.388(3) . ?
C41 C42 1.532(3) . ?
C44 C43 1.523(3) . ?
C28 C29 1.441(3) . ?
C28 C27 1.390(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.360(3) . ?
C39 H39 0.9300 . ?
C56 C51 1.400(3) . ?
C56 C55 1.394(3) . ?
C50 C51 1.444(3) . ?
C50 C49 1.394(3) . ?
C12 C7 1.398(3) . ?
C12 C11 1.390(3) . ?
C58 H58 0.9300 . ?
C29 C30 1.394(3) . ?
C14 H14 0.9300 . ?
C1 C6 1.403(3) . ?
C1 C2 1.388(3) . ?
C51 C52 1.393(3) . ?
C17 H17 0.9300 . ?
C19 C20 1.526(8) . ?
C19 C20A 1.540(10) . ?
C64 C63 1.521(3) . ?
C64 C65 1.515(3) . ?
C22 C21 1.519(3) . ?
C6 C7 1.446(3) . ?
C6 C5 1.394(3) . ?
C66 C65 1.522(3) . ?
C7 C8 1.399(3) . ?
C33 H33 0.9300 . ?
C33 C32 1.384(3) . ?
C42 C43 1.523(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.391(3) . ?
C49 H49 0.9300 . ?
C49 C48 1.375(4) . ?
C55 H55 0.9300 . ?
C55 C54 1.383(3) . ?
C46 H46 0.9300 . ?
C46 C47 1.386(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.388(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.371(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.370(4) . ?
C20 C21 1.476(8) . ?
C52 H52 0.9300 . ?
C52 C53 1.378(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.388(3) . ?
C54 H54 0.9300 . ?
C54 C53 1.386(4) . ?
C48 H48 0.9300 . ?
C48 C47 1.384(4) . ?
C25 H25 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.377(4) . ?
C32 H32 0.9300 . ?
C32 C31 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.374(4) . ?
C47 H47 0.9300 . ?
C31 H31 0.9300 . ?
C53 H53 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
F1 C21 1.530(8) . ?
C21 F4 1.218(5) . ?
C21 F1A 1.242(5) . ?
C21 F4A 1.539(8) . ?
C21 C20A 1.508(9) . ?
F3A C20A 1.345(12) . ?
C20A F2A 1.309(12) . ?
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
F12 C64 C63 O5 64.0(3) . . . . ?
F12 C64 C63 C62 -116.01(18) . . . . ?
F12 C64 C65 F11 -0.8(3) . . . . ?
F12 C64 C65 F10 -120.4(2) . . . . ?
F12 C64 C65 C66 118.6(2) . . . . ?
F9 C64 C63 O5 -52.9(3) . . . . ?
F9 C64 C63 C62 127.10(19) . . . . ?
F9 C64 C65 F11 118.4(2) . . . . ?
F9 C64 C65 F10 -1.3(3) . . . . ?
F9 C64 C65 C66 -122.3(2) . . . . ?
N4 C37 C36 C35 -1.5(3) . . . . ?
N4 C40 C41 O3 0.2(4) . . . . ?
N4 C40 C41 C42 179.56(17) . . . . ?
N4 C40 C44 O4 1.7(4) . . . . ?
N4 C40 C44 C43 -177.14(17) . . . . ?
N4 C38 C39 C35 1.1(3) . . . . ?
O3 C41 C42 F8 55.3(3) . . . . ?
O3 C41 C42 F5 -63.0(3) . . . . ?
O3 C41 C42 C43 175.8(2) . . . . ?
N2 C18 C19 O1 -3.5(4) . . . . ?
N2 C18 C19 C20 171.8(4) . . . . ?
N2 C18 C19 C20A 179.6(8) . . . . ?
N2 C18 C22 O2 0.9(4) . . . . ?
N2 C18 C22 C21 -178.2(2) . . . . ?
N2 C16 C17 C13 0.3(3) . . . . ?
N2 C15 C14 C13 -0.1(3) . . . . ?
O1 C19 C20 F3 -48.4(8) . . . . ?
O1 C19 C20 F2 67.8(8) . . . . ?
O1 C19 C20 C21 -173.6(4) . . . . ?
O1 C19 C20A C21 -179.4(6) . . . . ?
O1 C19 C20A F3A -66.8(12) . . . . ?
O1 C19 C20A F2A 54.0(11) . . . . ?
N6 C62 C63 O5 -6.1(4) . . . . ?
N6 C62 C63 C64 173.95(17) . . . . ?
N6 C62 C66 O6 6.6(4) . . . . ?
N6 C62 C66 C65 -174.21(18) . . . . ?
N6 C59 C58 C57 -1.1(3) . . . . ?
N3 C35 C36 C37 -171.32(17) . . . . ?
N3 C35 C39 C38 171.50(17) . . . . ?
N3 C23 C28 C29 -1.4(2) . . . . ?
N3 C23 C28 C27 -178.60(18) . . . . ?
N3 C23 C24 C25 176.9(2) . . . . ?
N3 C34 C29 C28 -0.4(2) . . . . ?
N3 C34 C29 C30 179.09(18) . . . . ?
N3 C34 C33 C32 -179.71(19) . . . . ?
F8 C42 C43 F7 5.0(3) . . . . ?
F8 C42 C43 F6 -112.7(2) . . . . ?
F8 C42 C43 C44 124.1(2) . . . . ?
N5 C57 C58 C59 -175.44(18) . . . . ?
N5 C45 C50 C51 -0.3(2) . . . . ?
N5 C45 C50 C49 -179.21(17) . . . . ?
N5 C45 C46 C47 178.7(2) . . . . ?
N5 C56 C51 C50 -0.9(2) . . . . ?
N5 C56 C51 C52 179.99(17) . . . . ?
N5 C56 C55 C54 179.1(2) . . . . ?
O2 C22 C21 C20 -172.7(4) . . . . ?
O2 C22 C21 F1 -71.7(5) . . . . ?
O2 C22 C21 F4 38.8(9) . . . . ?
O2 C22 C21 F1A -32.6(9) . . . . ?
O2 C22 C21 F4A 77.9(5) . . . . ?
O2 C22 C21 C20A 179.2(8) . . . . ?
N1 C13 C14 C15 -179.20(18) . . . . ?
N1 C13 C17 C16 179.10(18) . . . . ?
N1 C12 C7 C6 0.3(2) . . . . ?
N1 C12 C7 C8 -177.04(18) . . . . ?
N1 C12 C11 C10 175.8(2) . . . . ?
N1 C1 C6 C7 2.3(2) . . . . ?
N1 C1 C6 C5 -176.90(18) . . . . ?
N1 C1 C2 C3 176.3(2) . . . . ?
O6 C66 C65 F11 -64.6(3) . . . . ?
O6 C66 C65 F10 53.7(3) . . . . ?
O6 C66 C65 C64 175.3(2) . . . . ?
F5 C42 C43 F7 123.8(2) . . . . ?
F5 C42 C43 F6 6.1(3) . . . . ?
F5 C42 C43 C44 -117.2(2) . . . . ?
O4 C44 C43 F7 -62.7(3) . . . . ?
O4 C44 C43 F6 54.0(3) . . . . ?
O4 C44 C43 C42 178.2(2) . . . . ?
F3 C20 C21 C22 -134.0(6) . . . . ?
F3 C20 C21 F1 120.5(7) . . . . ?
F3 C20 C21 F4 12.4(12) . . . . ?
C13 N1 C12 C7 -171.04(17) . . . . ?
C13 N1 C12 C11 14.2(3) . . . . ?
C13 N1 C1 C6 169.94(17) . . . . ?
C13 N1 C1 C2 -6.3(3) . . . . ?
C35 N3 C23 C28 -173.11(17) . . . . ?
C35 N3 C23 C24 12.7(3) . . . . ?
C35 N3 C34 C29 173.89(17) . . . . ?
C35 N3 C34 C33 -3.3(3) . . . . ?
C18 N2 C16 C17 179.87(18) . . . . ?
C18 N2 C15 C14 180.00(17) . . . . ?
C18 C19 C20 F3 135.7(6) . . . . ?
C18 C19 C20 F2 -108.1(6) . . . . ?
C18 C19 C20 C21 10.5(6) . . . . ?
C18 C19 C20A C21 -2.1(12) . . . . ?
C18 C19 C20A F3A 110.6(14) . . . . ?
C18 C19 C20A F2A -128.6(11) . . . . ?
C18 C22 C21 C20 6.6(5) . . . . ?
C18 C22 C21 F1 107.6(5) . . . . ?
C18 C22 C21 F4 -142.0(8) . . . . ?
C18 C22 C21 F1A 146.6(9) . . . . ?
C18 C22 C21 F4A -102.8(5) . . . . ?
C18 C22 C21 C20A -1.5(8) . . . . ?
F2 C20 C21 C22 109.4(6) . . . . ?
F2 C20 C21 F1 3.9(7) . . . . ?
F2 C20 C21 F4 -104.2(11) . . . . ?
C23 N3 C35 C36 -154.70(17) . . . . ?
C23 N3 C35 C39 26.3(3) . . . . ?
C23 N3 C34 C29 -0.5(2) . . . . ?
C23 N3 C34 C33 -177.6(2) . . . . ?
C23 C28 C29 C34 1.1(2) . . . . ?
C23 C28 C29 C30 -178.3(2) . . . . ?
C23 C28 C27 C26 1.4(3) . . . . ?
C23 C24 C25 C26 -0.8(4) . . . . ?
C34 N3 C35 C36 32.0(3) . . . . ?
C34 N3 C35 C39 -146.99(18) . . . . ?
C34 N3 C23 C28 1.2(2) . . . . ?
C34 N3 C23 C24 -173.0(2) . . . . ?
C34 C29 C30 C31 0.8(3) . . . . ?
C34 C33 C32 C31 -1.0(3) . . . . ?
C37 N4 C40 C41 140.15(19) . . . . ?
C37 N4 C40 C44 -42.4(3) . . . . ?
C37 N4 C38 C39 5.5(3) . . . . ?
C61 C57 C58 C59 3.5(3) . . . . ?
C62 N6 C59 C58 175.00(18) . . . . ?
C62 N6 C60 C61 -174.67(17) . . . . ?
C62 C66 C65 F11 116.0(2) . . . . ?
C62 C66 C65 F10 -125.7(2) . . . . ?
C62 C66 C65 C64 -4.1(3) . . . . ?
C36 C35 C39 C38 -7.5(3) . . . . ?
C40 N4 C37 C36 172.60(17) . . . . ?
C40 N4 C38 C39 -172.36(17) . . . . ?
C40 C41 C42 F8 -124.16(19) . . . . ?
C40 C41 C42 F5 117.5(2) . . . . ?
C40 C41 C42 C43 -3.6(2) . . . . ?
C40 C44 C43 F7 116.32(19) . . . . ?
C40 C44 C43 F6 -127.0(2) . . . . ?
C40 C44 C43 C42 -2.8(2) . . . . ?
C59 N6 C62 C63 179.65(19) . . . . ?
C59 N6 C62 C66 1.6(3) . . . . ?
C59 N6 C60 C61 2.0(3) . . . . ?
C60 N6 C62 C63 -3.7(3) . . . . ?
C60 N6 C62 C66 178.23(18) . . . . ?
C60 N6 C59 C58 -1.7(3) . . . . ?
C60 C61 C57 N5 175.74(17) . . . . ?
C60 C61 C57 C58 -3.1(3) . . . . ?
C57 N5 C45 C50 173.63(17) . . . . ?
C57 N5 C45 C46 -3.5(3) . . . . ?
C57 N5 C56 C51 -173.23(17) . . . . ?
C57 N5 C56 C55 11.2(3) . . . . ?
C57 C61 C60 N6 0.5(3) . . . . ?
C38 N4 C37 C36 -5.3(3) . . . . ?
C38 N4 C40 C41 -42.0(3) . . . . ?
C38 N4 C40 C44 135.47(19) . . . . ?
C16 N2 C18 C19 165.43(18) . . . . ?
C16 N2 C18 C22 -16.4(3) . . . . ?
C16 N2 C15 C14 -1.5(3) . . . . ?
C45 N5 C57 C61 40.2(3) . . . . ?
C45 N5 C57 C58 -140.98(19) . . . . ?
C45 N5 C56 C51 0.7(2) . . . . ?
C45 N5 C56 C55 -174.9(2) . . . . ?
C45 C50 C51 C56 0.7(2) . . . . ?
C45 C50 C51 C52 179.7(2) . . . . ?
C45 C50 C49 C48 -0.2(3) . . . . ?
C45 C46 C47 C48 -0.1(4) . . . . ?
C41 C40 C44 O4 179.4(2) . . . . ?
C41 C40 C44 C43 0.6(2) . . . . ?
C41 C42 C43 F7 -115.17(19) . . . . ?
C41 C42 C43 F6 127.1(2) . . . . ?
C41 C42 C43 C44 3.9(2) . . . . ?
C44 C40 C41 O3 -177.4(2) . . . . ?
C44 C40 C41 C42 1.9(2) . . . . ?
C28 C23 C24 C25 3.3(3) . . . . ?
C28 C29 C30 C31 -179.9(2) . . . . ?
C28 C27 C26 C25 1.1(4) . . . . ?
C15 N2 C18 C19 -16.1(3) . . . . ?
C15 N2 C18 C22 162.14(19) . . . . ?
C15 N2 C16 C17 1.3(3) . . . . ?
C39 C35 C36 C37 7.7(3) . . . . ?
C56 N5 C57 C61 -147.04(19) . . . . ?
C56 N5 C57 C58 31.8(3) . . . . ?
C56 N5 C45 C50 -0.2(2) . . . . ?
C56 N5 C45 C46 -177.4(2) . . . . ?
C56 C51 C52 C53 0.7(3) . . . . ?
C56 C55 C54 C53 -0.8(3) . . . . ?
C50 C45 C46 C47 1.9(3) . . . . ?
C50 C51 C52 C53 -178.2(2) . . . . ?
C50 C49 C48 C47 1.9(4) . . . . ?
C12 N1 C13 C14 35.3(3) . . . . ?
C12 N1 C13 C17 -145.59(19) . . . . ?
C12 N1 C1 C6 -2.1(2) . . . . ?
C12 N1 C1 C2 -178.3(2) . . . . ?
C12 C7 C8 C9 1.2(3) . . . . ?
C12 C11 C10 C9 -0.9(3) . . . . ?
C29 C34 C33 C32 3.4(3) . . . . ?
C29 C28 C27 C26 -175.0(2) . . . . ?
C29 C30 C31 C32 1.7(4) . . . . ?
C14 C13 C17 C16 -1.8(3) . . . . ?
C1 N1 C13 C14 -135.3(2) . . . . ?
C1 N1 C13 C17 43.7(3) . . . . ?
C1 N1 C12 C7 1.0(2) . . . . ?
C1 N1 C12 C11 -173.7(2) . . . . ?
C1 C6 C7 C12 -1.6(2) . . . . ?
C1 C6 C7 C8 175.3(2) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C51 C56 C55 C54 4.0(3) . . . . ?
C51 C50 C49 C48 -178.7(2) . . . . ?
C51 C52 C53 C54 2.5(3) . . . . ?
C17 C13 C14 C15 1.7(3) . . . . ?
C19 C18 C22 O2 179.3(2) . . . . ?
C19 C18 C22 C21 0.2(3) . . . . ?
C19 C20 C21 C22 -10.3(6) . . . . ?
C19 C20 C21 F1 -115.8(6) . . . . ?
C19 C20 C21 F4 136.1(9) . . . . ?
C22 C18 C19 O1 178.1(2) . . . . ?
C22 C18 C19 C20 -6.6(4) . . . . ?
C22 C18 C19 C20A 1.2(8) . . . . ?
C22 C21 C20A C19 2.1(12) . . . . ?
C22 C21 C20A F3A -114.4(11) . . . . ?
C22 C21 C20A F2A 124.2(12) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C6 C7 C8 C9 -175.4(2) . . . . ?
C6 C5 C4 C3 0.5(4) . . . . ?
C63 C62 C66 O6 -171.7(3) . . . . ?
C63 C62 C66 C65 7.5(3) . . . . ?
C63 C64 C65 F11 -119.7(2) . . . . ?
C63 C64 C65 F10 120.7(2) . . . . ?
C63 C64 C65 C66 -0.4(2) . . . . ?
C66 C62 C63 O5 172.2(3) . . . . ?
C66 C62 C63 C64 -7.8(2) . . . . ?
C7 C12 C11 C10 1.6(3) . . . . ?
C7 C6 C5 C4 -179.1(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C33 C34 C29 C28 177.11(18) . . . . ?
C33 C34 C29 C30 -3.4(3) . . . . ?
C33 C32 C31 C30 -1.6(4) . . . . ?
C24 C23 C28 C29 173.45(18) . . . . ?
C24 C23 C28 C27 -3.7(3) . . . . ?
C49 C50 C51 C56 179.4(2) . . . . ?
C49 C50 C51 C52 -1.6(4) . . . . ?
C49 C48 C47 C46 -1.8(4) . . . . ?
C55 C56 C51 C50 175.15(18) . . . . ?
C55 C56 C51 C52 -4.0(3) . . . . ?
C55 C54 C53 C52 -2.4(4) . . . . ?
C46 C45 C50 C51 177.12(18) . . . . ?
C46 C45 C50 C49 -1.8(3) . . . . ?
C11 C12 C7 C6 175.60(18) . . . . ?
C11 C12 C7 C8 -1.8(3) . . . . ?
C11 C10 C9 C8 0.4(4) . . . . ?
C2 C1 C6 C7 178.88(18) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C27 C28 C29 C34 177.9(2) . . . . ?
C27 C28 C29 C30 -1.5(4) . . . . ?
C27 C26 C25 C24 -1.5(4) . . . . ?
C65 C64 C63 O5 -175.2(2) . . . . ?
C65 C64 C63 C62 4.8(2) . . . . ?
C5 C6 C7 C12 177.4(2) . . . . ?
C5 C6 C7 C8 -5.7(4) . . . . ?
F1A C21 C20A C19 -143.0(10) . . . . ?
F1A C21 C20A F3A 100.5(13) . . . . ?
F1A C21 C20A F2A -20.9(16) . . . . ?
F4A C21 C20A C19 108.1(10) . . . . ?
F4A C21 C20A F3A -8.4(11) . . . . ?
F4A C21 C20A F2A -129.8(12) . . . . ?
