#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:10:24 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291042 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159802.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_7159802
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         'C0.5 H Cl, C32 H15 F14 N5'
_chemical_formula_sum            'C32.5 H16 Cl F14 N5'
_chemical_formula_weight         777.95
_chemical_name_systematic        5,15-perfluoropropyl-10-(4-cyanophenyl)-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             2022-01-24
_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                111.2842(18)
_cell_angle_beta                 103.5014(18)
_cell_angle_gamma                95.1944(16)
_cell_formula_units_Z            2
_cell_length_a                   9.21263(19)
_cell_length_b                   12.5354(2)
_cell_length_c                   15.5289(3)
_cell_measurement_reflns_used    18302
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.7210
_cell_measurement_theta_min      3.1660
_cell_volume                     1594.14(6)
_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      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -53.00   1.00    2.50    --  -40.79 -57.00  46.00   56
  2  ω    -48.00 -14.00   1.00    2.50    --  -40.79 -57.00  46.00   34
  3  ω     88.00 113.00   1.00    2.50    --   40.79  57.00-171.00   25
  4  ω     14.00  41.00   1.00    2.50    --   40.79  57.00-171.00   27
  5  ω     57.00 130.00   1.00   15.00    --  105.59 -57.00  46.00   73
  6  ω     84.00 116.00   1.00   15.00    --  105.59  57.00-171.00   32
  7  ω    -69.00  32.00   1.00    2.50    --  -40.79  57.00-171.00  101
  8  ω    -81.00 -56.00   1.00    2.50    --  -40.79 -77.00-150.00   25
  9  ω    -43.00  -8.00   1.00    2.50    --  -40.79 -77.00-150.00   35
 10  ω   -114.00 -17.00   1.00    2.50    --  -40.79 -38.00 120.00   97
 11  ω     23.00  97.00   1.00    2.50    --   40.79-125.00  30.00   74
 12  ω    -23.00  27.00   1.00    2.50    --   40.79 -57.00  46.00   50
 13  ω      9.00  35.00   1.00    2.50    --   42.00  79.00-166.18   26
 14  ω     11.00  36.00   1.00    2.50    --   46.00  84.00-149.93   25
 15  ω     13.00  39.00   1.00    2.50    --   46.00  79.00-100.68   26
 16  ω     16.00  43.00   1.00    2.50    --   50.00  82.00  47.57   27
 17  ω     17.00  42.00   1.00    2.50    --   50.00  78.00 -51.38   25
 18  ω     16.00  41.00   1.00    2.50    --   50.00  81.00 150.32   25
 19  ω     16.00  41.00   1.00    2.50    --   50.00  82.00 102.64   25
 20  ω     26.00  54.00   1.00    2.50    --   58.00  75.00  -7.48   28
 21  ω     31.00  56.00   1.00    2.50    --   62.00  75.00  96.01   25
 22  ω     30.00  59.00   1.00    2.50    --   62.00  77.00-167.19   29
 23  ω     30.00  56.00   1.00    2.50    --   62.00  77.00  15.55   26
 24  ω     30.00  56.00   1.00    2.50    --   62.00  77.00 -62.03   26
 25  ω     31.00  57.00   1.00    2.50    --   62.00  75.00-123.02   26
 26  ω     36.00  62.00   1.00    2.50    --   66.00  72.00 153.48   26
 27  ω     33.00  63.00   1.00    2.50    --   66.00  77.00-106.59   30
 28  ω     37.00  63.00   1.00    2.50    --   70.00  77.00-164.79   26
 29  ω     39.00  66.00   1.00    2.50    --   70.00  75.00  30.53   27
 30  ω     40.00  69.00   1.00    2.50    --   70.00  77.00  47.72   29
 31  ω     48.00  74.00   1.00   15.00    --   74.00  63.00 132.41   26
 32  ω     42.00  69.00   1.00   15.00    --   74.00  76.00 150.20   27
 33  ω     42.00  74.00   1.00   15.00    --   74.00  75.00 -22.19   32
 34  ω     46.00  77.00   1.00   15.00    --   78.00  74.00 -53.25   31
 35  ω     48.00  78.00   1.00   15.00    --   78.00  73.00 -98.57   30
 36  ω     53.00  87.00   1.00   15.00    --   82.00  62.00  18.51   34
 37  ω     89.00 155.00   1.00   15.00    --   82.00  77.00  81.58   66
 38  ω     52.00  80.00   1.00   15.00    --   82.00  77.00  81.58   28
 39  ω     51.00  80.00   1.00   15.00    --   82.00  70.00-119.00   29
 40  ω    104.00 153.00   1.00   15.00    --   82.00  62.00  18.51   49
 41  ω     55.00  86.00   1.00   15.00    --   86.00  69.00  54.78   31
 42  ω     54.00  80.00   1.00   15.00    --   86.00  75.00 124.93   26
 43  ω    101.00 159.00   1.00   15.00    --   94.00  72.00 167.11   58
 44  ω     63.00  89.00   1.00   15.00    --   94.00  72.00 167.11   26
 45  ω     66.00 101.00   1.00   15.00    --   94.00  69.00-102.53   35
 46  ω    104.00 170.00   1.00   15.00    --   98.00  71.00-117.14   66
 47  ω     65.00  95.00   1.00   15.00    --   98.00  77.00-171.08   30
 48  ω     67.00  98.00   1.00   15.00    --   98.00  71.00-117.14   31
 49  ω     78.00 156.00   1.00   15.00    --  105.59  57.00 -46.68   78
 50  ω     84.00 154.00   1.00   15.00    --  105.59  61.00  90.00   70
 51  ω    147.00 178.00   1.00   15.00    --  105.59 125.00 -60.00   31
 52  ω     73.00  98.00   1.00   15.00    --  105.59  77.00 -60.00   25
 53  ω    110.00 159.00   1.00   15.00    --  105.59  77.00 -90.00   49
 54  ω     95.00 174.00   1.00   15.00    --  105.59 125.00  30.00   79
 55  ω     89.00 118.00   1.00   15.00    --  105.59-125.00  60.00   29
 56  ω     74.00 100.00   1.00   15.00    --  105.59  77.00 -90.00   26
 57  ω     32.00  85.00   1.00   15.00    --  105.59-125.00  60.00   53
 58  ω     73.00 108.00   1.00   15.00    --  105.59  77.00  60.00   35
 59  ω     74.00 117.00   1.00   15.00    --  105.59  77.00   0.00   43
 60  ω     73.00 172.00   1.00   15.00    --  105.59  77.00-150.00   99
 61  ω     76.00 166.00   1.00   15.00    --  105.59  64.00  29.23   90
 62  ω     77.00 171.00   1.00   15.00    --  105.59  77.00 120.00   94
 63  ω     25.00 109.00   1.00   15.00    --  105.59 -94.00  60.00   84
 64  ω     33.00 116.00   1.00   15.00    --  105.59-125.00 -90.00   83
 65  ω     73.00 174.00   1.00   15.00    --  105.59  77.00 -30.00  101
 66  ω     26.00  95.00   1.00   15.00    --  105.59 -94.00 -30.00   69
;
_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      -0.1413905000
_diffrn_orient_matrix_UB_12      0.0255765000
_diffrn_orient_matrix_UB_13      0.0349445000
_diffrn_orient_matrix_UB_21      -0.0851148000
_diffrn_orient_matrix_UB_22      -0.1251428000
_diffrn_orient_matrix_UB_23      -0.0674091000
_diffrn_orient_matrix_UB_31      0.0590742000
_diffrn_orient_matrix_UB_32      -0.0419209000
_diffrn_orient_matrix_UB_33      0.0811663000
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28537
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.889
_diffrn_reflns_theta_min         3.188
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73783
_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    1.621
_exptl_crystal_description       plate
_exptl_crystal_F_000             778
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Heptane'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0035(6)
_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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6238
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0728
_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)+(0.1315P)²+1.1831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2244
_refine_ls_wR_factor_ref         0.2292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5676
_reflns_number_total             6238
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00191e2.cif
_cod_data_source_block           pgj277
_cod_depositor_comments
'Adding full bibliography for 7159800--7159804.cif.'
_cod_original_formula_sum        'C32.50 H16 Cl F14 N5'
_cod_database_code               7159802
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c32 h15 f14 n5'
_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   0.939
_shelx_estimated_absorpt_t_min   0.586
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 Cl1-C33
 1.85 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim C33: within 1.9A with sigma of 0.01 and sigma for terminal atoms of
0.001 within 1.9A
4. Others
 Fixed Sof: C33(0.5) H33A(0.5) H33B(0.5) F7(0.75) F8(0.25)
5.a Riding coordinates:
 N1(H1), N2(H2), N4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C8(H8), C9(H9), C13(H13), C14(H14), C18(H18), C19(H19),
 C24(H24), C25(H25), C27(H27), C28(H28)
;
_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 1.512
_oxdiff_exptl_absorpt_empirical_full_min 0.718
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
Cl1 Cl 0.8800(4) 0.9779(4) 0.9149(3) 0.2529(17) Uani 1 1 d D U . . .
C33 C 0.992(2) 0.8948(19) 0.9708(17) 0.217(5) Uani 0.5 1 d D U P . .
H33A H 1.051216 0.851543 0.930665 0.260 Uiso 0.5 1 calc R U P . .
H33B H 0.929554 0.841910 0.986121 0.260 Uiso 0.5 1 calc R U P . .
F1 F -0.0135(2) 0.50694(16) 0.15180(11) 0.0605(5) Uani 1 1 d . . . . .
F2 F -0.10861(19) 0.65865(18) 0.21210(13) 0.0621(5) Uani 1 1 d . . . . .
F3 F 0.1632(5) 0.7977(2) 0.2827(2) 0.1405(16) Uani 1 1 d . . . . .
F4 F 0.2771(3) 0.6595(3) 0.2466(3) 0.1253(13) Uani 1 1 d . . . . .
F5 F 0.2459(4) 0.7756(3) 0.1304(2) 0.1111(10) Uani 1 1 d . . . . .
F6 F 0.1717(7) 0.5909(4) 0.0681(3) 0.187(2) Uani 1 1 d . . . . .
F9 F 0.3469(2) 0.58705(18) 0.91717(13) 0.0694(5) Uani 1 1 d . . . . .
F10 F 0.2859(2) 0.7559(2) 0.94678(12) 0.0724(6) Uani 1 1 d . . . . .
F11 F 0.6170(3) 0.6709(3) 0.89898(19) 0.1115(10) Uani 1 1 d . . . . .
F12 F 0.5539(3) 0.8378(3) 0.9244(2) 0.1099(10) Uani 1 1 d . . . . .
F13 F 0.7428(3) 0.8260(3) 1.0792(2) 0.1309(12) Uani 1 1 d . . . . .
F14 F 0.5326(4) 0.8644(4) 1.0969(2) 0.1429(15) Uani 1 1 d . . . . .
F15 F 0.5760(6) 0.6991(4) 1.0788(3) 0.186(2) Uani 1 1 d . . . . .
N1 N 0.1393(2) 0.70032(18) 0.66866(15) 0.0429(5) Uani 1 1 d . . . . .
H1 H 0.081066 0.621601 0.629902 0.052 Uiso 1 1 d R U . . .
N2 N 0.0462(2) 0.67849(18) 0.48680(15) 0.0409(5) Uani 1 1 d . . . . .
H2 H 0.095074 0.623749 0.495148 0.049 Uiso 1 1 d R U . . .
N3 N 0.1688(2) 0.49683(17) 0.42142(14) 0.0377(4) Uani 1 1 d . . . . .
N4 N 0.2995(2) 0.52570(18) 0.62584(14) 0.0417(5) Uani 1 1 d . . . . .
H4 H 0.285232 0.574137 0.599657 0.050 Uiso 1 1 d R U . . .
N5 N 0.6459(5) -0.1119(3) 0.3268(3) 0.0954(12) Uani 1 1 d . . . . .
C1 C 0.0915(3) 0.7941(2) 0.65247(19) 0.0455(6) Uani 1 1 d . . . . .
C2 C 0.0325(3) 0.7784(2) 0.55615(19) 0.0432(5) Uani 1 1 d . . . . .
C3 C -0.0274(3) 0.8479(2) 0.5082(2) 0.0509(6) Uani 1 1 d . . . . .
H3 H -0.051685 0.920433 0.536975 0.061 Uiso 1 1 calc R U . . .
C4 C -0.0436(3) 0.7899(2) 0.4116(2) 0.0504(6) Uani 1 1 d . . . . .
H4A H -0.082512 0.815506 0.363291 0.060 Uiso 1 1 calc R U . . .
C5 C 0.0099(3) 0.6831(2) 0.39850(18) 0.0411(5) Uani 1 1 d . . . . .
C6 C 0.0468(3) 0.5979(2) 0.32267(17) 0.0404(5) Uani 1 1 d . . . . .
C7 C 0.1288(3) 0.5115(2) 0.33542(17) 0.0401(5) Uani 1 1 d . . . . .
C8 C 0.1926(4) 0.4316(3) 0.2675(2) 0.0527(7) Uani 1 1 d . . . . .
H8 H 0.181758 0.423094 0.204198 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2698(4) 0.3724(3) 0.3121(2) 0.0527(7) Uani 1 1 d . . . . .
H9 H 0.323431 0.315670 0.285716 0.063 Uiso 1 1 calc R U . . .
C10 C 0.2551(3) 0.4122(2) 0.40893(18) 0.0404(5) Uani 1 1 d . . . . .
C11 C 0.3238(3) 0.3705(2) 0.47931(18) 0.0406(5) Uani 1 1 d . . . . .
C12 C 0.3367(3) 0.4205(2) 0.57826(18) 0.0412(5) Uani 1 1 d . . . . .
C13 C 0.3865(3) 0.3757(2) 0.6499(2) 0.0480(6) Uani 1 1 d . . . . .
H13 H 0.416682 0.304305 0.639014 0.058 Uiso 1 1 calc R U . . .
C14 C 0.3831(3) 0.4538(3) 0.7365(2) 0.0505(6) Uani 1 1 d . . . . .
H14 H 0.411915 0.445215 0.794763 0.061 Uiso 1 1 calc R U . . .
C15 C 0.3279(3) 0.5511(2) 0.72355(18) 0.0443(6) Uani 1 1 d . . . . .
C16 C 0.3028(3) 0.6537(2) 0.79024(18) 0.0469(6) Uani 1 1 d . . . . .
C17 C 0.2266(3) 0.7341(2) 0.76267(18) 0.0475(6) Uani 1 1 d . . . . .
C18 C 0.2296(4) 0.8550(3) 0.8074(2) 0.0613(8) Uani 1 1 d . . . . .
H18 H 0.278885 0.902366 0.871689 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1481(4) 0.8912(3) 0.7405(2) 0.0588(7) Uani 1 1 d . . . . .
H19 H 0.132978 0.966889 0.751723 0.071 Uiso 1 1 calc R U . . .
C20 C 0.0160(3) 0.6108(2) 0.22777(19) 0.0468(6) Uani 1 1 d . . . . .
C21 C 0.1481(3) 0.6903(3) 0.2201(2) 0.0555(7) Uani 1 1 d . . . . .
C22 C 0.1367(6) 0.6981(6) 0.1250(4) 0.1062(18) Uani 1 1 d . . . . .
C23 C 0.3926(3) 0.2649(2) 0.44666(19) 0.0427(6) Uani 1 1 d . . . . .
C24 C 0.3105(3) 0.1641(2) 0.3669(2) 0.0506(6) Uani 1 1 d . . . . .
H24 H 0.211526 0.162910 0.334236 0.061 Uiso 1 1 calc R U . . .
C25 C 0.3737(3) 0.0667(2) 0.3359(2) 0.0574(7) Uani 1 1 d . . . . .
H25 H 0.318059 0.000612 0.282297 0.069 Uiso 1 1 calc R U . . .
C26 C 0.5221(3) 0.0673(2) 0.3853(2) 0.0545(7) Uani 1 1 d . . . . .
C27 C 0.6038(3) 0.1662(3) 0.4651(2) 0.0550(7) Uani 1 1 d . . . . .
H27 H 0.701498 0.166529 0.499148 0.066 Uiso 1 1 calc R U . . .
C28 C 0.5403(3) 0.2640(2) 0.4942(2) 0.0500(6) Uani 1 1 d . . . . .
H28 H 0.597326 0.330765 0.546638 0.060 Uiso 1 1 calc R U . . .
C29 C 0.5904(4) -0.0333(3) 0.3527(3) 0.0683(9) Uani 1 1 d . . . . .
C30 C 0.3637(3) 0.6828(3) 0.89715(19) 0.0541(7) Uani 1 1 d . . . . .
C31 C 0.5331(4) 0.7417(3) 0.9417(2) 0.0660(8) Uani 1 1 d . . . . .
C32 C 0.5985(5) 0.7792(5) 1.0505(3) 0.0947(14) Uani 1 1 d . . . . .
F7 F 0.0111(5) 0.6804(5) 0.0677(3) 0.1158(15) Uani 0.75 1 d . . P A 1
F8 F 0.0350(11) 0.8026(13) 0.1499(12) 0.122(5) Uani 0.25 1 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'
Cl Cl 0.3639 0.7018 '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'
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
C33 Cl1 C33 80.9(10) . 2_777 ?
Cl1 C33 Cl1 99.1(10) . 2_777 ?
Cl1 C33 H33A 111.9 2_777 . ?
Cl1 C33 H33A 111.9 . . ?
Cl1 C33 H33B 111.9 . . ?
Cl1 C33 H33B 111.9 2_777 . ?
H33A C33 H33B 109.6 . . ?
C1 N1 H1 120.6 . . ?
C1 N1 C17 111.0(2) . . ?
C17 N1 H1 122.7 . . ?
C2 N2 H2 127.6 . . ?
C5 N2 H2 118.9 . . ?
C5 N2 C2 111.5(2) . . ?
C10 N3 C7 106.8(2) . . ?
C12 N4 H4 121.0 . . ?
C12 N4 C15 111.4(2) . . ?
C15 N4 H4 125.6 . . ?
N1 C1 C2 116.8(2) . . ?
N1 C1 C19 106.5(2) . . ?
C2 C1 C19 134.9(3) . . ?
N2 C2 C1 117.5(2) . . ?
N2 C2 C3 106.5(2) . . ?
C1 C2 C3 135.6(2) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 C2 108.1(2) . . ?
C4 C3 H3 126.0 . . ?
C3 C4 H4A 126.1 . . ?
C3 C4 C5 107.9(2) . . ?
C5 C4 H4A 126.1 . . ?
N2 C5 C4 105.7(2) . . ?
N2 C5 C6 118.6(2) . . ?
C6 C5 C4 135.1(2) . . ?
C5 C6 C7 123.1(2) . . ?
C5 C6 C20 117.3(2) . . ?
C7 C6 C20 119.0(2) . . ?
N3 C7 C6 123.2(2) . . ?
N3 C7 C8 108.7(2) . . ?
C6 C7 C8 128.0(2) . . ?
C7 C8 H8 126.2 . . ?
C9 C8 C7 107.6(2) . . ?
C9 C8 H8 126.2 . . ?
C8 C9 H9 126.2 . . ?
C8 C9 C10 107.7(2) . . ?
C10 C9 H9 126.2 . . ?
N3 C10 C9 109.2(2) . . ?
N3 C10 C11 126.4(2) . . ?
C11 C10 C9 124.4(2) . . ?
C10 C11 C23 117.8(2) . . ?
C12 C11 C10 126.3(2) . . ?
C12 C11 C23 115.9(2) . . ?
N4 C12 C11 125.6(2) . . ?
N4 C12 C13 105.4(2) . . ?
C11 C12 C13 129.0(2) . . ?
C12 C13 H13 125.4 . . ?
C14 C13 C12 109.2(2) . . ?
C14 C13 H13 125.4 . . ?
C13 C14 H14 125.6 . . ?
C13 C14 C15 108.8(2) . . ?
C15 C14 H14 125.6 . . ?
N4 C15 C14 105.3(2) . . ?
N4 C15 C16 123.9(2) . . ?
C16 C15 C14 130.8(2) . . ?
C15 C16 C17 123.1(2) . . ?
C15 C16 C30 119.3(3) . . ?
C17 C16 C30 117.5(2) . . ?
N1 C17 C16 119.5(2) . . ?
N1 C17 C18 105.4(2) . . ?
C16 C17 C18 134.6(3) . . ?
C17 C18 H18 125.5 . . ?
C19 C18 C17 109.0(3) . . ?
C19 C18 H18 125.5 . . ?
C1 C19 H19 126.0 . . ?
C18 C19 C1 108.0(3) . . ?
C18 C19 H19 126.0 . . ?
F1 C20 F2 105.6(2) . . ?
F1 C20 C6 112.4(2) . . ?
F1 C20 C21 107.1(2) . . ?
F2 C20 C6 111.2(2) . . ?
F2 C20 C21 106.0(2) . . ?
C6 C20 C21 113.9(2) . . ?
F3 C21 C20 109.0(3) . . ?
F3 C21 C22 106.2(4) . . ?
F4 C21 F3 104.9(3) . . ?
F4 C21 C20 110.1(3) . . ?
F4 C21 C22 107.6(4) . . ?
C22 C21 C20 118.2(3) . . ?
F5 C22 F6 102.7(5) . . ?
F5 C22 C21 112.1(4) . . ?
F5 C22 F8 88.0(5) . . ?
F6 C22 C21 104.2(4) . . ?
F6 C22 F8 156.0(7) . . ?
C21 C22 F8 91.2(6) . . ?
F7 C22 F5 119.3(5) . . ?
F7 C22 F6 93.2(5) . . ?
F7 C22 C21 119.8(4) . . ?
C24 C23 C11 120.8(2) . . ?
C28 C23 C11 121.1(2) . . ?
C28 C23 C24 118.1(2) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.1(2) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C29 120.4(3) . . ?
C27 C26 C25 119.5(3) . . ?
C27 C26 C29 120.1(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.1(3) . . ?
C28 C27 H27 120.0 . . ?
C23 C28 H28 119.3 . . ?
C27 C28 C23 121.3(3) . . ?
C27 C28 H28 119.3 . . ?
N5 C29 C26 179.0(4) . . ?
F9 C30 C16 111.8(2) . . ?
F9 C30 C31 106.9(3) . . ?
F10 C30 F9 106.1(2) . . ?
F10 C30 C16 110.4(2) . . ?
F10 C30 C31 106.6(3) . . ?
C16 C30 C31 114.7(2) . . ?
F11 C31 F12 107.4(3) . . ?
F11 C31 C30 109.5(3) . . ?
F11 C31 C32 107.5(4) . . ?
F12 C31 C30 108.6(3) . . ?
F12 C31 C32 106.4(3) . . ?
C32 C31 C30 116.9(3) . . ?
F13 C32 F14 104.7(4) . . ?
F13 C32 C31 111.1(4) . . ?
F14 C32 C31 109.4(4) . . ?
F15 C32 F13 110.9(5) . . ?
F15 C32 F14 106.5(5) . . ?
F15 C32 C31 113.7(4) . . ?
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
Cl1 C33 1.829(5) . ?
Cl1 C33 1.93(3) 2_777 ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
F1 C20 1.353(3) . ?
F2 C20 1.356(3) . ?
F3 C21 1.316(4) . ?
F4 C21 1.304(4) . ?
F5 C22 1.299(5) . ?
F6 C22 1.428(8) . ?
F9 C30 1.349(4) . ?
F10 C30 1.346(4) . ?
F11 C31 1.327(4) . ?
F12 C31 1.333(5) . ?
F13 C32 1.305(5) . ?
F14 C32 1.339(6) . ?
F15 C32 1.252(6) . ?
N1 H1 0.9726 . ?
N1 C1 1.376(3) . ?
N1 C17 1.378(3) . ?
N2 H2 0.8851 . ?
N2 C2 1.363(3) . ?
N2 C5 1.357(3) . ?
N3 C7 1.384(3) . ?
N3 C10 1.367(3) . ?
N4 H4 0.8486 . ?
N4 C12 1.376(3) . ?
N4 C15 1.386(3) . ?
N5 C29 1.136(4) . ?
C1 C2 1.400(4) . ?
C1 C19 1.403(4) . ?
C2 C3 1.409(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(4) . ?
C4 H4A 0.9300 . ?
C4 C5 1.430(4) . ?
C5 C6 1.408(4) . ?
C6 C7 1.420(3) . ?
C6 C20 1.505(3) . ?
C7 C8 1.445(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.332(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.446(4) . ?
C10 C11 1.422(4) . ?
C11 C12 1.404(4) . ?
C11 C23 1.492(3) . ?
C12 C13 1.423(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.355(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.424(4) . ?
C15 C16 1.407(4) . ?
C16 C17 1.412(4) . ?
C16 C30 1.514(4) . ?
C17 C18 1.414(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.557(4) . ?
C21 C22 1.495(5) . ?
C22 F7 1.228(6) . ?
C22 F8 1.663(15) . ?
C23 C24 1.399(4) . ?
C23 C28 1.391(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.377(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.400(4) . ?
C26 C27 1.385(4) . ?
C26 C29 1.440(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(4) . ?
C28 H28 0.9300 . ?
C30 C31 1.541(4) . ?
C31 C32 1.528(5) . ?
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
C33 Cl1 C33 Cl1 -0.003(2) 2_777 . . 2_777 ?
F1 C20 C21 F3 169.5(3) . . . . ?
F1 C20 C21 F4 -75.9(3) . . . . ?
F1 C20 C21 C22 48.2(5) . . . . ?
F2 C20 C21 F3 57.1(3) . . . . ?
F2 C20 C21 F4 171.7(3) . . . . ?
F2 C20 C21 C22 -64.2(4) . . . . ?
F3 C21 C22 F5 50.9(6) . . . . ?
F3 C21 C22 F6 161.2(4) . . . . ?
F3 C21 C22 F7 -96.5(7) . . . . ?
F3 C21 C22 F8 -37.4(6) . . . . ?
F4 C21 C22 F5 -61.0(6) . . . . ?
F4 C21 C22 F6 49.3(5) . . . . ?
F4 C21 C22 F7 151.6(6) . . . . ?
F4 C21 C22 F8 -149.3(5) . . . . ?
F9 C30 C31 F11 63.7(3) . . . . ?
F9 C30 C31 F12 -179.2(3) . . . . ?
F9 C30 C31 C32 -58.8(4) . . . . ?
F10 C30 C31 F11 176.8(3) . . . . ?
F10 C30 C31 F12 -66.2(3) . . . . ?
F10 C30 C31 C32 54.3(5) . . . . ?
F11 C31 C32 F13 55.4(6) . . . . ?
F11 C31 C32 F14 170.5(4) . . . . ?
F11 C31 C32 F15 -70.7(6) . . . . ?
F12 C31 C32 F13 -59.5(6) . . . . ?
F12 C31 C32 F14 55.6(5) . . . . ?
F12 C31 C32 F15 174.5(5) . . . . ?
N1 C1 C2 N2 -8.8(4) . . . . ?
N1 C1 C2 C3 179.9(3) . . . . ?
N1 C1 C19 C18 0.7(4) . . . . ?
N1 C17 C18 C19 -1.0(4) . . . . ?
N2 C2 C3 C4 -1.9(3) . . . . ?
N2 C5 C6 C7 -4.1(4) . . . . ?
N2 C5 C6 C20 -175.4(2) . . . . ?
N3 C7 C8 C9 -0.8(3) . . . . ?
N3 C10 C11 C12 -11.0(4) . . . . ?
N3 C10 C11 C23 170.5(2) . . . . ?
N4 C12 C13 C14 -1.9(3) . . . . ?
N4 C15 C16 C17 8.9(4) . . . . ?
N4 C15 C16 C30 -169.0(2) . . . . ?
C1 N1 C17 C16 -171.7(2) . . . . ?
C1 N1 C17 C18 1.4(3) . . . . ?
C1 C2 C3 C4 170.0(3) . . . . ?
C2 N2 C5 C4 -5.3(3) . . . . ?
C2 N2 C5 C6 167.5(2) . . . . ?
C2 C1 C19 C18 -162.9(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 N2 3.9(3) . . . . ?
C3 C4 C5 C6 -167.0(3) . . . . ?
C4 C5 C6 C7 166.0(3) . . . . ?
C4 C5 C6 C20 -5.3(4) . . . . ?
C5 N2 C2 C1 -169.0(2) . . . . ?
C5 N2 C2 C3 4.6(3) . . . . ?
C5 C6 C7 N3 5.7(4) . . . . ?
C5 C6 C7 C8 -169.9(3) . . . . ?
C5 C6 C20 F1 -151.3(2) . . . . ?
C5 C6 C20 F2 -33.1(3) . . . . ?
C5 C6 C20 C21 86.6(3) . . . . ?
C6 C7 C8 C9 175.3(3) . . . . ?
C6 C20 C21 F3 -65.5(4) . . . . ?
C6 C20 C21 F4 49.1(4) . . . . ?
C6 C20 C21 C22 173.3(4) . . . . ?
C7 N3 C10 C9 -0.1(3) . . . . ?
C7 N3 C10 C11 178.5(2) . . . . ?
C7 C6 C20 F1 37.0(3) . . . . ?
C7 C6 C20 F2 155.2(2) . . . . ?
C7 C6 C20 C21 -85.1(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 N3 -0.5(3) . . . . ?
C8 C9 C10 C11 -179.1(3) . . . . ?
C9 C10 C11 C12 167.4(3) . . . . ?
C9 C10 C11 C23 -11.2(4) . . . . ?
C10 N3 C7 C6 -175.8(2) . . . . ?
C10 N3 C7 C8 0.5(3) . . . . ?
C10 C11 C12 N4 -7.5(4) . . . . ?
C10 C11 C12 C13 171.4(3) . . . . ?
C10 C11 C23 C24 -50.2(3) . . . . ?
C10 C11 C23 C28 129.4(3) . . . . ?
C11 C12 C13 C14 179.1(3) . . . . ?
C11 C23 C24 C25 179.5(3) . . . . ?
C11 C23 C28 C27 179.1(3) . . . . ?
C12 N4 C15 C14 -1.3(3) . . . . ?
C12 N4 C15 C16 179.1(2) . . . . ?
C12 C11 C23 C24 131.1(3) . . . . ?
C12 C11 C23 C28 -49.3(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 N4 0.1(3) . . . . ?
C13 C14 C15 C16 179.6(3) . . . . ?
C14 C15 C16 C17 -170.5(3) . . . . ?
C14 C15 C16 C30 11.5(4) . . . . ?
C15 N4 C12 C11 -179.0(2) . . . . ?
C15 N4 C12 C13 2.0(3) . . . . ?
C15 C16 C17 N1 17.0(4) . . . . ?
C15 C16 C17 C18 -153.7(3) . . . . ?
C15 C16 C30 F9 -40.0(4) . . . . ?
C15 C16 C30 F10 -157.8(3) . . . . ?
C15 C16 C30 C31 81.8(4) . . . . ?
C16 C17 C18 C19 170.7(3) . . . . ?
C16 C30 C31 F11 -60.7(4) . . . . ?
C16 C30 C31 F12 56.3(4) . . . . ?
C16 C30 C31 C32 176.7(4) . . . . ?
C17 N1 C1 C2 165.7(2) . . . . ?
C17 N1 C1 C19 -1.3(3) . . . . ?
C17 C16 C30 F9 141.9(3) . . . . ?
C17 C16 C30 F10 24.1(4) . . . . ?
C17 C16 C30 C31 -96.3(3) . . . . ?
C17 C18 C19 C1 0.2(4) . . . . ?
C19 C1 C2 N2 153.5(3) . . . . ?
C19 C1 C2 C3 -17.7(6) . . . . ?
C20 C6 C7 N3 176.9(2) . . . . ?
C20 C6 C7 C8 1.3(4) . . . . ?
C20 C21 C22 F5 173.6(4) . . . . ?
C20 C21 C22 F6 -76.1(5) . . . . ?
C20 C21 C22 F7 26.2(8) . . . . ?
C20 C21 C22 F8 85.3(6) . . . . ?
C23 C11 C12 N4 171.1(2) . . . . ?
C23 C11 C12 C13 -10.1(4) . . . . ?
C23 C24 C25 C26 0.7(5) . . . . ?
C24 C23 C28 C27 -1.2(4) . . . . ?
C24 C25 C26 C27 0.1(5) . . . . ?
C24 C25 C26 C29 -179.0(3) . . . . ?
C25 C26 C27 C28 -1.5(5) . . . . ?
C26 C27 C28 C23 2.1(5) . . . . ?
C28 C23 C24 C25 -0.2(4) . . . . ?
C29 C26 C27 C28 177.7(3) . . . . ?
C30 C16 C17 N1 -165.0(2) . . . . ?
C30 C16 C17 C18 24.3(5) . . . . ?
C30 C31 C32 F13 179.0(4) . . . . ?
C30 C31 C32 F14 -66.0(5) . . . . ?
C30 C31 C32 F15 52.9(7) . . . . ?
