#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:10:24 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291042 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159800.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_7159800
loop_
_publ_author_name
'Julliard, Paul-Gabriel'
'Pascal, Simon'
'Siri, Olivier'
'Giorgi, Michel'
'Cortés-Arriagada, Diego'
'Sanhueza, Luis'
'Canard, Gabriel'
_publ_section_title
;
 Two-step access to bis-meso-perfluoroalkyl-corroles towards
 meso-perfluoroacyl-ABC-corroles.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1993
_journal_page_last               1997
_journal_paper_doi               10.1039/d4ob00191e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H18 F6 N4 O, C6 H6'
_chemical_formula_sum            'C34 H24 F6 N4 O'
_chemical_formula_weight         618.57
_chemical_name_systematic        5,15-bis-trifluoromethyl-10-(p-anisyl)-corrole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-02 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                102.813(7)
_cell_angle_beta                 106.382(7)
_cell_angle_gamma                97.930(7)
_cell_formula_units_Z            2
_cell_length_a                   10.9445(10)
_cell_length_b                   11.6383(9)
_cell_length_c                   12.2119(9)
_cell_measurement_reflns_used    3697
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3140
_cell_measurement_theta_min      3.9860
_cell_volume                     1421.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  -1.00   1.00    5.00    --    0.00 105.00 -44.00   28
  2  ω      8.00  36.00   1.00    5.00    --    0.00-105.00-145.00   28
  3  ω    -75.00 -48.00   1.00   10.00    --  -54.96 105.00 -44.00   27
  4  ω   -149.00 -86.00   1.00   10.00    --  -54.96-105.00-145.00   63
  5  ω    102.00 130.00   1.00   10.00    --   54.96 105.00 -44.00   28
  6  ω     28.00 106.00   1.00   10.00    --   54.96-105.00-145.00   78
  7  ω    102.00 129.00   1.00   35.00    --  109.93 105.00 -44.00   27
  8  ω     70.00 112.00   1.00   35.00    --  109.93-105.00-145.00   42
  9  ω    -94.00 -27.00   1.00    5.00    --    0.00 -57.00 150.00   67
 10  ω    -12.00  43.00   1.00    5.00    --    0.00 -57.00 150.00   55
 11  ω   -114.00 -80.00   1.00   10.00    --  -54.96 -99.00 -60.00   34
 12  ω    -91.00  -9.00   1.00   10.00    --  -54.96 125.00  60.00   82
 13  ω   -150.00 -79.00   1.00   10.00    --  -54.96 -99.00 -90.00   71
 14  ω   -134.00 -79.00   1.00   10.00    --  -54.96 -99.00  60.00   55
 15  ω     65.00  92.00   1.00   10.00    --   54.96 -38.00  30.00   27
 16  ω    -36.00 -11.00   1.00   10.00    --   54.96 -38.00  30.00   25
 17  ω     14.00 147.00   1.00   10.00    --   54.96  57.00 -60.00  133
 18  ω    104.00 142.00   1.00   10.00    --   54.96 125.00-180.00   38
 19  ω     95.00 178.00   1.00   35.00    --  109.93  38.00 120.00   83
 20  ω     64.00  91.00   1.00   35.00    --  109.93 -91.00 150.00   27
 21  ω    101.00 170.00   1.00   35.00    --  109.93 111.00 -30.00   69
 22  ω     26.00 150.00   1.00   35.00    --  109.93 -91.00 -60.00  124
 23  ω     63.00  94.00   1.00   35.00    --  109.93  38.00 120.00   31
 24  ω    101.00 152.00   1.00   35.00    --  109.93 -91.00   0.00   51
 25  ω    146.00 177.00   1.00   35.00    --  109.93  63.00  30.00   31
 26  ω     67.00 118.00   1.00   35.00    --  109.93  63.00  30.00   51
 27  ω    135.00 160.00   1.00   35.00    --  109.93  77.00  90.00   25
 28  ω     70.00 139.00   1.00   35.00    --  109.93 178.00-120.00   69
 29  ω    100.00 177.00   1.00   35.00    --  109.93 111.00   0.00   77
 30  ω     73.00 100.00   1.00   35.00    --  109.93  77.00  90.00   27
 31  ω     80.00 112.00   1.00   35.00    --  109.93-111.00  90.00   32
 32  ω     31.00  58.00   1.00   35.00    --  109.93 -91.00 150.00   27
 33  ω     75.00 145.00   1.00   35.00    --  109.93 -50.00-120.00   70
 34  ω    123.00 150.00   1.00   35.00    --  109.93 -91.00 150.00   27
 35  ω    100.00 157.00   1.00   35.00    --  109.93 111.00 -60.00   57
 36  ω     39.00  64.00   1.00   35.00    --  109.93 -91.00   0.00   25
 37  ω     80.00 178.00   1.00   35.00    --  109.93  50.00  60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1331637000
_diffrn_orient_matrix_UB_12      -0.0364545000
_diffrn_orient_matrix_UB_13      0.0248907000
_diffrn_orient_matrix_UB_21      0.0422005000
_diffrn_orient_matrix_UB_22      0.0794344000
_diffrn_orient_matrix_UB_23      0.1289114000
_diffrn_orient_matrix_UB_31      -0.0552808000
_diffrn_orient_matrix_UB_32      -0.1080614000
_diffrn_orient_matrix_UB_33      0.0381256000
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10539
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.684
_diffrn_reflns_theta_min         3.988
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Heptane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         5291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0967
_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)+(0.1692P)²+0.6403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2826
_refine_ls_wR_factor_ref         0.3258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3300
_reflns_number_total             5291
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00191e2.cif
_cod_data_source_block           pgj293
_cod_depositor_comments
'Adding full bibliography for 7159800--7159804.cif.'
_cod_database_code               7159800
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c28 h18 f6 n4 o1'
_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   0.925
_shelx_estimated_absorpt_t_min   0.874
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1), N2(H2), N4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C8(H8), C9(H9), C12(H12), C13(H13), C17(H17), C18(H18),
 C21(H21), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34)
2.c Fitted hexagon refined as free rotating group:
 C29(C30,C31,C32,C33,C34)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.661
_oxdiff_exptl_absorpt_empirical_full_min 0.683
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9448(7) 0.7834(4) 0.1128(5) 0.147(2) Uani 1 1 d . . . . .
F2 F 0.7602(5) 0.7979(5) 0.1256(5) 0.156(3) Uani 1 1 d . . . . .
F3 F 0.9294(5) 0.9076(3) 0.2562(4) 0.1037(14) Uani 1 1 d . . . . .
F4 F 0.8008(4) 0.1252(3) 0.6349(3) 0.0890(11) Uani 1 1 d . . . . .
F5 F 0.6175(4) 0.1746(4) 0.6004(4) 0.0941(12) Uani 1 1 d . . . . .
F6 F 0.7754(5) 0.2749(4) 0.7545(3) 0.1072(14) Uani 1 1 d . . . . .
O1 O 0.7133(4) -0.1166(3) -0.2467(3) 0.0758(11) Uani 1 1 d . . . . .
N1 N 0.8218(4) 0.4842(3) 0.2295(3) 0.0510(8) Uani 1 1 d . . . . .
H1 H 0.771785 0.489556 0.272332 0.061 Uiso 1 1 d R U . . .
N2 N 0.9049(4) 0.6558(3) 0.4379(3) 0.0521(9) Uani 1 1 d . . . . .
H2 H 0.932325 0.588725 0.419257 0.063 Uiso 1 1 d R U . . .
N3 N 0.8657(4) 0.4959(3) 0.5555(3) 0.0520(9) Uani 1 1 d . . . . .
N4 N 0.7928(4) 0.3061(3) 0.3728(3) 0.0490(8) Uani 1 1 d . . . . .
H4 H 0.827921 0.381275 0.404922 0.059 Uiso 1 1 d R U . . .
C1 C 0.7748(4) 0.2602(4) 0.1592(4) 0.0498(10) Uani 1 1 d . . . . .
C2 C 0.8076(4) 0.3763(4) 0.1460(4) 0.0489(9) Uani 1 1 d . . . . .
C3 C 0.8411(5) 0.4084(4) 0.0522(4) 0.0568(11) Uani 1 1 d . . . . .
H3 H 0.843529 0.354484 -0.015444 0.068 Uiso 1 1 calc R U . . .
C4 C 0.8692(5) 0.5302(5) 0.0756(4) 0.0613(12) Uani 1 1 d . . . . .
H4A H 0.892565 0.573433 0.026419 0.074 Uiso 1 1 calc R U . . .
C5 C 0.8570(5) 0.5805(4) 0.1877(4) 0.0524(10) Uani 1 1 d . . . . .
C6 C 0.8801(5) 0.7028(4) 0.2535(5) 0.0579(11) Uani 1 1 d . . . . .
C7 C 0.8929(5) 0.7376(4) 0.3739(4) 0.0563(11) Uani 1 1 d . . . . .
C8 C 0.8854(5) 0.8444(4) 0.4551(5) 0.0651(13) Uani 1 1 d . . . . .
H8 H 0.879656 0.918128 0.438679 0.078 Uiso 1 1 calc R U . . .
C9 C 0.8880(5) 0.8206(4) 0.5605(5) 0.0648(13) Uani 1 1 d . . . . .
H9 H 0.883974 0.874906 0.627166 0.078 Uiso 1 1 calc R U . . .
C10 C 0.8981(4) 0.6988(4) 0.5504(4) 0.0543(11) Uani 1 1 d . . . . .
C11 C 0.8798(4) 0.6134(4) 0.6126(4) 0.0531(10) Uani 1 1 d . . . . .
C12 C 0.8512(6) 0.6215(5) 0.7219(4) 0.0673(13) Uani 1 1 d . . . . .
H12 H 0.854104 0.691641 0.777589 0.081 Uiso 1 1 calc R U . . .
C13 C 0.8193(6) 0.5069(5) 0.7277(4) 0.0661(13) Uani 1 1 d . . . . .
H13 H 0.797795 0.483555 0.789133 0.079 Uiso 1 1 calc R U . . .
C14 C 0.8249(4) 0.4270(4) 0.6196(4) 0.0524(10) Uani 1 1 d . . . . .
C15 C 0.7852(5) 0.3011(4) 0.5704(4) 0.0536(10) Uani 1 1 d . . . . .
C16 C 0.7719(4) 0.2439(4) 0.4512(4) 0.0507(10) Uani 1 1 d . . . . .
C17 C 0.7285(5) 0.1208(4) 0.3855(4) 0.0559(11) Uani 1 1 d . . . . .
H17 H 0.705822 0.056980 0.415238 0.067 Uiso 1 1 calc R U . . .
C18 C 0.7255(5) 0.1115(4) 0.2720(4) 0.0579(11) Uani 1 1 d . . . . .
H18 H 0.701225 0.040391 0.210953 0.070 Uiso 1 1 calc R U . . .
C19 C 0.7661(4) 0.2297(4) 0.2625(4) 0.0484(9) Uani 1 1 d . . . . .
C20 C 0.7527(4) 0.1584(4) 0.0513(4) 0.0497(10) Uani 1 1 d . . . . .
C21 C 0.8385(5) 0.0802(5) 0.0516(5) 0.0652(13) Uani 1 1 d . . . . .
H21 H 0.907741 0.089450 0.120043 0.078 Uiso 1 1 calc R U . . .
C22 C 0.8215(6) -0.0107(5) -0.0491(5) 0.0685(13) Uani 1 1 d . . . . .
H22 H 0.879521 -0.062118 -0.048114 0.082 Uiso 1 1 calc R U . . .
C23 C 0.7193(5) -0.0256(4) -0.1507(4) 0.0565(11) Uani 1 1 d . . . . .
C24 C 0.6325(5) 0.0482(5) -0.1513(5) 0.0669(13) Uani 1 1 d . . . . .
H24 H 0.561727 0.037063 -0.219101 0.080 Uiso 1 1 calc R U . . .
C25 C 0.6503(5) 0.1393(5) -0.0506(5) 0.0652(13) Uani 1 1 d . . . . .
H25 H 0.590975 0.189400 -0.051930 0.078 Uiso 1 1 calc R U . . .
C26 C 0.6095(6) -0.1371(6) -0.3524(5) 0.0825(17) Uani 1 1 d . . . . .
H26A H 0.619121 -0.200300 -0.412894 0.124 Uiso 1 1 calc R U . . .
H26B H 0.610068 -0.064537 -0.377516 0.124 Uiso 1 1 calc R U . . .
H26C H 0.528483 -0.160455 -0.339078 0.124 Uiso 1 1 calc R U . . .
C27 C 0.8790(7) 0.7963(5) 0.1872(6) 0.0737(15) Uani 1 1 d . . . . .
C28 C 0.7460(6) 0.2214(5) 0.6399(5) 0.0672(13) Uani 1 1 d . . . . .
C29 C 0.4536(6) 0.3692(4) 0.7159(9) 0.142(4) Uani 1 1 d G . . . .
H29 H 0.430749 0.285397 0.692546 0.170 Uiso 1 1 calc R U . . .
C30 C 0.4293(5) 0.4333(7) 0.6314(5) 0.124(3) Uani 1 1 d G . . . .
H30 H 0.390124 0.392288 0.551517 0.149 Uiso 1 1 calc R U . . .
C31 C 0.4635(6) 0.5586(7) 0.6664(5) 0.110(3) Uani 1 1 d G . . . .
H31 H 0.447203 0.601423 0.609855 0.132 Uiso 1 1 calc R U . . .
C32 C 0.5220(6) 0.6198(4) 0.7858(7) 0.111(3) Uani 1 1 d G . . . .
H32 H 0.544908 0.703669 0.809222 0.133 Uiso 1 1 calc R U . . .
C33 C 0.5464(6) 0.5558(8) 0.8703(4) 0.125(3) Uani 1 1 d G . . . .
H33 H 0.585534 0.596780 0.950253 0.151 Uiso 1 1 calc R U . . .
C34 C 0.5122(7) 0.4305(8) 0.8354(8) 0.134(4) Uani 1 1 d G . . . .
H34 H 0.528456 0.387644 0.891917 0.161 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'
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
C23 O1 C26 118.0(4) . . ?
C2 N1 H1 120.0 . . ?
C5 N1 H1 119.6 . . ?
C5 N1 C2 110.0(3) . . ?
C7 N2 H2 125.1 . . ?
C7 N2 C10 113.1(4) . . ?
C10 N2 H2 120.3 . . ?
C14 N3 C11 108.4(4) . . ?
C16 N4 H4 114.1 . . ?
C19 N4 H4 134.3 . . ?
C19 N4 C16 111.1(4) . . ?
C2 C1 C19 127.5(4) . . ?
C2 C1 C20 115.2(4) . . ?
C19 C1 C20 117.3(4) . . ?
N1 C2 C1 125.7(4) . . ?
N1 C2 C3 105.9(4) . . ?
C3 C2 C1 128.3(4) . . ?
C2 C3 H3 125.3 . . ?
C4 C3 C2 109.5(4) . . ?
C4 C3 H3 125.3 . . ?
C3 C4 H4A 125.8 . . ?
C3 C4 C5 108.4(4) . . ?
C5 C4 H4A 125.8 . . ?
N1 C5 C4 106.2(4) . . ?
N1 C5 C6 123.4(4) . . ?
C4 C5 C6 130.4(4) . . ?
C5 C6 C27 117.6(5) . . ?
C7 C6 C5 123.0(4) . . ?
C7 C6 C27 119.2(5) . . ?
N2 C7 C6 120.0(4) . . ?
N2 C7 C8 104.2(4) . . ?
C6 C7 C8 135.5(5) . . ?
C7 C8 H8 125.4 . . ?
C9 C8 C7 109.3(4) . . ?
C9 C8 H8 125.4 . . ?
C8 C9 H9 125.9 . . ?
C8 C9 C10 108.2(4) . . ?
C10 C9 H9 125.9 . . ?
N2 C10 C9 105.1(4) . . ?
N2 C10 C11 116.8(4) . . ?
C11 C10 C9 136.8(4) . . ?
N3 C11 C10 117.3(4) . . ?
N3 C11 C12 109.5(4) . . ?
C10 C11 C12 132.4(4) . . ?
C11 C12 H12 126.7 . . ?
C13 C12 C11 106.6(4) . . ?
C13 C12 H12 126.7 . . ?
C12 C13 H13 126.4 . . ?
C12 C13 C14 107.3(4) . . ?
C14 C13 H13 126.4 . . ?
N3 C14 C13 108.2(4) . . ?
N3 C14 C15 119.1(4) . . ?
C15 C14 C13 132.3(4) . . ?
C14 C15 C16 122.7(4) . . ?
C14 C15 C28 121.0(4) . . ?
C16 C15 C28 116.2(4) . . ?
N4 C16 C15 123.2(4) . . ?
N4 C16 C17 106.0(4) . . ?
C15 C16 C17 130.7(4) . . ?
C16 C17 H17 125.6 . . ?
C18 C17 C16 108.7(4) . . ?
C18 C17 H17 125.6 . . ?
C17 C18 H18 125.9 . . ?
C17 C18 C19 108.1(4) . . ?
C19 C18 H18 125.9 . . ?
N4 C19 C1 127.5(4) . . ?
N4 C19 C18 106.1(4) . . ?
C1 C19 C18 126.4(4) . . ?
C21 C20 C1 120.3(4) . . ?
C25 C20 C1 122.0(4) . . ?
C25 C20 C21 117.7(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.5(5) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.3(5) . . ?
C23 C22 H22 119.8 . . ?
O1 C23 C22 115.6(4) . . ?
C24 C23 O1 124.6(5) . . ?
C24 C23 C22 119.8(5) . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.6(5) . . ?
C25 C24 H24 120.2 . . ?
C20 C25 C24 122.1(5) . . ?
C20 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F1 C27 F2 106.5(6) . . ?
F1 C27 F3 104.1(5) . . ?
F1 C27 C6 114.5(5) . . ?
F2 C27 F3 105.3(5) . . ?
F2 C27 C6 111.8(5) . . ?
F3 C27 C6 113.8(5) . . ?
F4 C28 F5 104.4(5) . . ?
F4 C28 C15 113.3(4) . . ?
F5 C28 C15 112.7(4) . . ?
F6 C28 F4 105.2(5) . . ?
F6 C28 F5 105.9(5) . . ?
F6 C28 C15 114.4(5) . . ?
C30 C29 H29 120.0 . . ?
C30 C29 C34 120.0 . . ?
C34 C29 H29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C29 C30 C31 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C29 C34 H34 120.0 . . ?
C33 C34 C29 120.0 . . ?
C33 C34 H34 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C27 1.306(8) . ?
F2 C27 1.311(8) . ?
F3 C27 1.323(7) . ?
F4 C28 1.339(7) . ?
F5 C28 1.340(7) . ?
F6 C28 1.325(7) . ?
O1 C23 1.373(5) . ?
O1 C26 1.406(7) . ?
N1 H1 0.8564 . ?
N1 C2 1.389(5) . ?
N1 C5 1.383(6) . ?
N2 H2 0.8806 . ?
N2 C7 1.357(6) . ?
N2 C10 1.381(6) . ?
N3 C11 1.356(6) . ?
N3 C14 1.354(6) . ?
N4 H4 0.8587 . ?
N4 C16 1.371(5) . ?
N4 C19 1.365(5) . ?
C1 C2 1.406(6) . ?
C1 C19 1.408(6) . ?
C1 C20 1.499(6) . ?
C2 C3 1.405(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(7) . ?
C4 H4A 0.9300 . ?
C4 C5 1.415(7) . ?
C5 C6 1.419(7) . ?
C6 C7 1.397(7) . ?
C6 C27 1.493(7) . ?
C7 C8 1.436(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.417(7) . ?
C10 C11 1.403(7) . ?
C11 C12 1.442(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.353(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.459(6) . ?
C14 C15 1.408(7) . ?
C15 C16 1.416(6) . ?
C15 C28 1.486(7) . ?
C16 C17 1.418(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.357(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.427(6) . ?
C20 C21 1.394(7) . ?
C20 C25 1.370(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(8) . ?
C23 C24 1.365(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(7) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C29 H29 0.9300 . ?
C29 C30 1.3900 . ?
C29 C34 1.3900 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C33 H33 0.9300 . ?
C33 C34 1.3900 . ?
C34 H34 0.9300 . ?
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 C23 C24 C25 -178.0(5) . . . . ?
N1 C2 C3 C4 -2.3(6) . . . . ?
N1 C5 C6 C7 12.0(8) . . . . ?
N1 C5 C6 C27 -162.6(5) . . . . ?
N2 C7 C8 C9 -2.3(6) . . . . ?
N2 C10 C11 N3 -2.3(6) . . . . ?
N2 C10 C11 C12 -170.4(5) . . . . ?
N3 C11 C12 C13 -0.4(6) . . . . ?
N3 C14 C15 C16 -7.2(7) . . . . ?
N3 C14 C15 C28 176.9(4) . . . . ?
N4 C16 C17 C18 0.6(5) . . . . ?
C1 C2 C3 C4 -178.3(5) . . . . ?
C1 C20 C21 C22 -177.4(5) . . . . ?
C1 C20 C25 C24 177.7(5) . . . . ?
C2 N1 C5 C4 -2.0(5) . . . . ?
C2 N1 C5 C6 -179.3(4) . . . . ?
C2 C1 C19 N4 -2.9(8) . . . . ?
C2 C1 C19 C18 176.2(5) . . . . ?
C2 C1 C20 C21 112.8(5) . . . . ?
C2 C1 C20 C25 -66.3(6) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 N1 0.5(6) . . . . ?
C3 C4 C5 C6 177.6(5) . . . . ?
C4 C5 C6 C7 -164.6(5) . . . . ?
C4 C5 C6 C27 20.8(8) . . . . ?
C5 N1 C2 C1 178.8(4) . . . . ?
C5 N1 C2 C3 2.7(5) . . . . ?
C5 C6 C7 N2 10.9(8) . . . . ?
C5 C6 C7 C8 -162.1(5) . . . . ?
C5 C6 C27 F1 -46.0(8) . . . . ?
C5 C6 C27 F2 75.3(7) . . . . ?
C5 C6 C27 F3 -165.6(5) . . . . ?
C6 C7 C8 C9 171.4(6) . . . . ?
C7 N2 C10 C9 -3.4(6) . . . . ?
C7 N2 C10 C11 166.0(4) . . . . ?
C7 C6 C27 F1 139.2(6) . . . . ?
C7 C6 C27 F2 -99.5(7) . . . . ?
C7 C6 C27 F3 19.6(8) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
C8 C9 C10 N2 1.7(6) . . . . ?
C8 C9 C10 C11 -164.3(6) . . . . ?
C9 C10 C11 N3 162.5(6) . . . . ?
C9 C10 C11 C12 -5.6(10) . . . . ?
C10 N2 C7 C6 -171.4(4) . . . . ?
C10 N2 C7 C8 3.5(5) . . . . ?
C10 C11 C12 C13 168.4(5) . . . . ?
C11 N3 C14 C13 -3.0(5) . . . . ?
C11 N3 C14 C15 170.9(4) . . . . ?
C11 C12 C13 C14 -1.4(6) . . . . ?
C12 C13 C14 N3 2.8(6) . . . . ?
C12 C13 C14 C15 -170.1(5) . . . . ?
C13 C14 C15 C16 165.0(5) . . . . ?
C13 C14 C15 C28 -10.9(8) . . . . ?
C14 N3 C11 C10 -168.6(4) . . . . ?
C14 N3 C11 C12 2.1(5) . . . . ?
C14 C15 C16 N4 -2.0(7) . . . . ?
C14 C15 C16 C17 -177.1(5) . . . . ?
C14 C15 C28 F4 -132.9(5) . . . . ?
C14 C15 C28 F5 108.8(6) . . . . ?
C14 C15 C28 F6 -12.2(7) . . . . ?
C15 C16 C17 C18 176.3(5) . . . . ?
C16 N4 C19 C1 179.3(4) . . . . ?
C16 N4 C19 C18 0.1(5) . . . . ?
C16 C15 C28 F4 51.0(6) . . . . ?
C16 C15 C28 F5 -67.3(6) . . . . ?
C16 C15 C28 F6 171.7(5) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C17 C18 C19 N4 0.3(5) . . . . ?
C17 C18 C19 C1 -179.0(5) . . . . ?
C19 N4 C16 C15 -176.5(4) . . . . ?
C19 N4 C16 C17 -0.4(5) . . . . ?
C19 C1 C2 N1 -8.6(8) . . . . ?
C19 C1 C2 C3 166.6(5) . . . . ?
C19 C1 C20 C21 -64.7(6) . . . . ?
C19 C1 C20 C25 116.3(5) . . . . ?
C20 C1 C2 N1 174.3(4) . . . . ?
C20 C1 C2 C3 -10.5(7) . . . . ?
C20 C1 C19 N4 174.2(4) . . . . ?
C20 C1 C19 C18 -6.7(7) . . . . ?
C20 C21 C22 C23 -0.3(9) . . . . ?
C21 C20 C25 C24 -1.4(8) . . . . ?
C21 C22 C23 O1 178.3(5) . . . . ?
C21 C22 C23 C24 -1.5(9) . . . . ?
C22 C23 C24 C25 1.8(9) . . . . ?
C23 C24 C25 C20 -0.4(9) . . . . ?
C25 C20 C21 C22 1.7(8) . . . . ?
C26 O1 C23 C22 179.0(5) . . . . ?
C26 O1 C23 C24 -1.2(8) . . . . ?
C27 C6 C7 N2 -174.6(5) . . . . ?
C27 C6 C7 C8 12.5(9) . . . . ?
C28 C15 C16 N4 174.0(4) . . . . ?
C28 C15 C16 C17 -1.0(7) . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C29 C34 C33 0.0 . . . . ?
C30 C31 C32 C33 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C29 0.0 . . . . ?
C34 C29 C30 C31 0.0 . . . . ?
