#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/73/2007323.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2007323
loop_
_publ_author_name
'Swenson, Dale C.'
'Yamamoto, Michiharu'
'Burton, Donald J.'
_publ_section_title
;
 3,4,5,6-Tetrafluoro-1,2,7,8-tetrakis(trifluoromethyl)phenanthrene and
 3,4,7,8-Tetrafluoro-1,2,5,6-tetrakis(trifluoromethyl)anthracene
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              846
_journal_page_last               849
_journal_paper_doi               10.1107/S0108270197019951
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C18 H2 F16'
_chemical_formula_sum            'C18 H2 F16'
_chemical_formula_weight         522.20
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                126.06(2)
_cell_angle_beta                 110.62(2)
_cell_angle_gamma                90.19(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2680(10)
_cell_length_b                   8.469(2)
_cell_length_c                   8.274(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      22.0
_cell_measurement_theta_min      14.0
_cell_volume                     421.0(2)
_computing_cell_refinement       'CAD-4 Operations Manual'
_computing_data_collection       'CAD-4 Operations Manual (Enraf-Nonius, 1977)'
_computing_data_reduction        'PROCESS in MolEN (Fair, 1990)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL (Sheldrick, 1995)'
_computing_structure_solution    'MULTAN80 (Main et al., 1980)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3758
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  240
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             254
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.206
_refine_ls_extinction_coef       0.042(8)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.110
_refine_ls_goodness_of_fit_obs   1.112
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1914
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.135
_refine_ls_restrained_S_obs      1.113
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_obs          .036
_refine_ls_shift/esd_max         -0.100
_refine_ls_shift/esd_mean        0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.1566P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.117
_refine_ls_wR_factor_obs         .104
_reflns_number_observed          1603
_reflns_number_total             1915
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            fg1361.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.1566P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.1566P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2007323
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 .0381(8) .0369(8) .0372(8) .0118(6) .0196(6) .0246(7)
C2 .0484(9) .0441(9) .0524(10) .0185(7) .0284(8) .0359(8)
F2 .0831(9) .0627(7) .0925(9) .0413(6) .0618(8) .0634(7)
C3 .0462(9) .0542(10) .0513(9) .0165(8) .0286(8) .0390(9)
F3 .0810(9) .0816(9) .0900(9) .0384(7) .0619(8) .0702(8)
C4 .0379(8) .0468(9) .0397(8) .0135(7) .0220(7) .0272(7)
C5 .0379(8) .0387(8) .0373(8) .0141(6) .0203(6) .0233(7)
C6 .0363(8) .0359(8) .0347(7) .0122(6) .0187(6) .0220(6)
C7 .0428(9) .0366(8) .0436(8) .0167(7) .0238(7) .0279(7)
C8 .0483(11) .0568(12) .0468(11) .0161(9) .0300(9) .0308(10)
F8A .0771(9) .0536(8) .0564(8) .0192(7) .0441(7) .0237(6)
F8B .0467(7) .0850(10) .0733(9) .0206(7) .0382(7) .0407(8)
F8C .1048(13) .1002(11) .0702(9) .0506(10) .0633(10) .0631(9)
C9 .0524(11) .0503(11) .0500(12) .0260(9) .0317(10) .0333(10)
F9A .0786(10) .1030(12) .0983(12) .0658(10) .0679(10) .0773(11)
F9B .0916(12) .0408(7) .0772(10) .0155(7) .0239(9) .0351(7)
F9C .0702(8) .0836(9) .0660(8) .0469(7) .0422(7) .0587(8)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 .9369(2) -.0771(2) .0814(3) .0353(3) Uani d . 1 . C
C2 .8727(2) -.1519(3) .1681(3) .0422(4) Uani d . 1 . C
F2 .9110(2) -.3185(2) .1372(2) .0609(4) Uani d . 1 . F
C3 .7775(2) -.0576(3) .2855(3) .0440(4) Uani d . 1 . C
F3 .7236(2) -.1384(2) .3632(2) .0641(4) Uani d . 1 . F
C4 .7304(2) .1186(3) .3214(3) .0397(4) Uani d D 1 . C
C5 .7740(2) .1853(2) .2209(3) .0370(4) Uani d D 1 . C
C6 .8864(2) .0954(2) .1075(3) .0347(3) Uani d . 1 . C
C7 .9542(2) .1697(2) .0248(3) .0374(4) Uani d . 1 . C
H7 .932(3) .284(3) .042(3) .047(5) Uiso d . 1 . H
C8 .6434(3) .2291(3) .4812(3) .0487(5) Uani d PD .946(2) 1 C
F8A .7035(2) .4299(2) .6055(2) .0646(4) Uani d P .946(2) 1 F
F8B .4656(2) .1764(2) .3769(3) .0704(5) Uani d P .946(2) 1 F
F8C .6841(2) .1906(3) .6228(3) .0761(5) Uani d P .946(2) 1 F
C8' .609(2) .212(3) .440(3) .049 Uiso d PGD .054(2) 2 C
F8A' .473(3) .236(4) .320(4) .073 Uiso d PG .054(2) 2 F
F8B' .548(4) .087(3) .463(4) .073 Uiso d PG .054(2) 2 F
F8C' .703(3) .390(4) .637(4) .073 Uiso d PG .054(2) 2 F
C9 .7027(3) .3492(3) .2174(3) .0463(5) Uani d PD .946(2) 1 C
F9A .5545(2) .3710(3) .2485(3) .0730(5) Uani d P .946(2) 1 F
F9B .8258(3) .5289(2) .3679(3) .0760(5) Uani d P .946(2) 1 F
F9C .6542(2) .3049(3) .0198(2) .0607(4) Uani d P .946(2) 1 F
C9' .752(3) .388(2) .270(4) .046 Uiso d PGD .054(2) 2 C
F9A' .646(4) .319(5) .066(3) .070 Uiso d PG .054(2) 2 F
F9B' .672(3) .487(4) .400(4) .070 Uiso d PG .054(2) 2 F
F9C' .904(3) .514(4) .347(5) .070 Uiso d PG .054(2) 2 F
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
C7 C1 C2 2_755 120.4(2) no
C7 C1 C6 2_755 121.99(14) no
C2 C1 C6 . 117.60(14) no
F2 C2 C3 . 119.18(15) no
F2 C2 C1 . 118.83(15) no
C3 C2 C1 . 122.0(2) no
F3 C3 C2 . 117.8(2) no
F3 C3 C4 . 120.4(2) no
C2 C3 C4 . 121.8(2) no
C5 C4 C3 . 118.39(15) no
C5 C4 C8 . 124.2(2) no
C3 C4 C8 . 117.3(2) no
C5 C4 C8' . 120.5(7) ?
C3 C4 C8' . 120.4(8) ?
C4 C5 C6 . 120.5(2) no
C4 C5 C9 . 122.12(15) no
C6 C5 C9 . 117.37(15) no
C4 C5 C9' . 123.3(8) ?
C6 C5 C9' . 114.4(8) ?
C7 C6 C1 . 116.74(14) no
C7 C6 C5 . 124.04(15) no
C1 C6 C5 . 119.21(14) no
C1 C7 C6 2_755 121.26(15) no
C1 C7 H7 2_755 117.0(13) ?
C6 C7 H7 . 121.7(13) ?
F8B C8 F8C . 106.8(2) ?
F8B C8 F8A . 108.2(2) ?
F8C C8 F8A . 105.9(2) ?
F8B C8 C4 . 112.9(2) ?
F8C C8 C4 . 111.6(2) ?
F8A C8 C4 . 111.1(2) ?
F8C' C8' F8A' . 109.5 ?
F8C' C8' F8B' . 109.4 ?
F8A' C8' F8B' . 109.5 ?
F8C' C8' C4 . 110.(2) ?
F8A' C8' C4 . 110.5(17) ?
F8B' C8' C4 . 107.7(16) ?
F9B C9 F9A . 108.5(2) ?
F9B C9 F9C . 106.7(2) ?
F9A C9 F9C . 104.1(2) ?
F9B C9 C5 . 111.8(2) ?
F9A C9 C5 . 113.6(2) ?
F9C C9 C5 . 111.6(2) ?
F9A' C9' F9C' . 109.5 ?
F9A' C9' F9B' . 109.5 ?
F9C' C9' F9B' . 109.5 ?
F9A' C9' C5 . 99.(2) ?
F9C' C9' C5 . 113.(2) ?
F9B' C9' C5 . 115.3(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C7 2_755 1.396(2) no
C1 C2 . 1.414(2) no
C1 C6 . 1.432(2) no
C2 F2 . 1.339(2) yes
C2 C3 . 1.352(2) no
C3 F3 . 1.341(2) yes
C3 C4 . 1.425(3) no
C4 C5 . 1.379(2) no
C4 C8 . 1.536(2) ?
C4 C8' . 1.541(9) ?
C5 C6 . 1.450(2) no
C5 C9 . 1.522(2) ?
C5 C9' . 1.545(9) ?
C6 C7 . 1.398(2) no
C7 C1 2_755 1.396(2) ?
C7 H7 . .92(2) ?
C8 F8B . 1.324(2) ?
C8 F8C . 1.328(3) ?
C8 F8A . 1.332(3) ?
C8' F8C' . 1.32 ?
C8' F8A' . 1.32 ?
C8' F8B' . 1.32 ?
C9 F9B . 1.330(3) ?
C9 F9A . 1.331(2) ?
C9 F9C . 1.338(2) ?
C9' F9A' . 1.32 ?
C9' F9C' . 1.32 ?
C9' F9B' . 1.32 ?
F2 F3 . 2.631(2) yes
F3 F8C . 2.437(2) no
F8A F9A . 2.488(2) no
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C1 C2 F2 2_755 . -3.2(3) ?
C6 C1 C2 F2 . . 177.0(2) ?
C7 C1 C2 C3 2_755 . 175.3(2) ?
C6 C1 C2 C3 . . -4.5(3) ?
F2 C2 C3 F3 . . -0.9(3) ?
C1 C2 C3 F3 . . -179.4(2) ?
F2 C2 C3 C4 . . -179.1(2) ?
C1 C2 C3 C4 . . 2.4(3) ?
F3 C3 C4 C5 . . -174.0(2) ?
C2 C3 C4 C5 . . 4.2(3) ?
F3 C3 C4 C8 . . 9.4(3) ?
C2 C3 C4 C8 . . -172.4(2) ?
F3 C3 C4 C8' . . -3.1(9) ?
C2 C3 C4 C8' . . 175.1(9) ?
C5 C4 C8 F8B . . 86.5(2) ?
C3 C4 C8 F8B . . -97.1(2) ?
C8' C4 C8 F8B . . 12.(4) ?
C5 C4 C8 F8C . . -153.2(2) ?
C3 C4 C8 F8C . . 23.2(2) ?
C8' C4 C8 F8C . . 132.(4) ?
C5 C4 C8 F8A . . -35.3(3) ?
C3 C4 C8 F8A . . 141.2(2) ?
C8' C4 C8 F8A . . -110.(4) ?
C5 C4 C8' F8C' . . -78.3(12) ?
C3 C4 C8' F8C' . . 111.0(11) ?
C8 C4 C8' F8C' . . 34.(4) ?
C5 C4 C8' F8A' . . 42.8(14) ?
C3 C4 C8' F8A' . . -127.9(11) ?
C8 C4 C8' F8A' . . 155.(5) ?
C5 C4 C8' F8B' . . 162.4(10) ?
C3 C4 C8' F8B' . . -8.3(14) ?
C8 C4 C8' F8B' . . -86.(4) ?
C3 C4 C5 C6 . . -8.4(2) yes
C8 C4 C5 C6 . . 168.0(2) ?
C8' C4 C5 C6 . . -179.3(9) ?
C3 C4 C5 C9 . . 169.6(2) ?
C8 C4 C5 C9 . . -14.0(3) yes
C8' C4 C5 C9 . . -1.2(9) ?
C3 C4 C5 C9' . . -172.0(11) ?
C8 C4 C5 C9' . . 4.4(11) ?
C8' C4 C5 C9' . . 17.1(14) ?
C4 C5 C9 F9B . . 101.8(2) ?
C6 C5 C9 F9B . . -80.1(2) ?
C9' C5 C9 F9B . . 3.(3) ?
C4 C5 C9 F9A . . -21.4(3) ?
C6 C5 C9 F9A . . 156.7(2) ?
C9' C5 C9 F9A . . -121.(3) ?
C4 C5 C9 F9C . . -138.7(2) ?
C6 C5 C9 F9C . . 39.3(2) ?
C9' C5 C9 F9C . . 122.(3) ?
C4 C5 C9' F9A' . . -123.2(12) ?
C6 C5 C9' F9A' . . 72.2(11) ?
C9 C5 C9' F9A' . . -32.(3) ?
C4 C5 C9' F9C' . . 120.8(13) ?
C6 C5 C9' F9C' . . -43.7(16) ?
C9 C5 C9' F9C' . . -148.(4) ?
C4 C5 C9' F9B' . . -7.(2) ?
C6 C5 C9' F9B' . . -171.0(13) ?
C9 C5 C9' F9B' . . 84.(3) ?
C7 C1 C6 C7 2_755 . -1.1(3) ?
C2 C1 C6 C7 . . 178.69(15) ?
C7 C1 C6 C5 2_755 . -179.54(15) ?
C2 C1 C6 C5 . . 0.3(2) ?
C4 C5 C6 C7 . . -172.0(2) ?
C9 C5 C6 C7 . . 9.8(2) ?
C9' C5 C6 C7 . . -7.0(10) ?
C4 C5 C6 C1 . . 6.2(2) ?
C9 C5 C6 C1 . . -171.9(2) ?
C9' C5 C6 C1 . . 171.2(10) ?
C1 C6 C7 C1 . 2_755 1.1(3) ?
C5 C6 C7 C1 . 2_755 179.45(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102316948