#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008276.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_2008276
loop_
_publ_author_name
'Leroy, Jacques'
'Bondon, Arnaud'
'Toupet, Loic'
_publ_section_title
2,3,7,8,12,13,17,18-Octafluoro-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              464
_journal_page_last               466
_journal_paper_doi               10.1107/S0108270198014000
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C44 H2 F28 N4'
_chemical_formula_sum            'C44 H2 F28 N4'
_chemical_formula_weight         1118.5
_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-97
_cell_angle_alpha                105.00(3)
_cell_angle_beta                 92.46(3)
_cell_angle_gamma                101.74(2)
_cell_formula_units_Z            1
_cell_length_a                   6.1818(10)
_cell_length_b                   13.008(3)
_cell_length_c                   13.605(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      9.0
_cell_volume                     1029.3(8)
_computing_cell_refinement       CAD4_Software
_computing_data_collection       CAD4_Software(Enraf-Nonius,_1977)
_computing_data_reduction        MolEN_(Fair,_1990)
_computing_molecular_graphics    ORTEPII_(Johnson,_1976)
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  Enraf_Nonius_CAD4
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4909
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.00
_exptl_absorpt_correction_T_min  0.00
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.219
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997a)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0644P)²+0.2708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                2901
_reflns_number_total             4481
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ln1059.cif
_cod_data_source_block           noyau
_cod_depositor_comments
;
Automatic conversion scripts had previously changed 
'_atom_site_refinement_flags' tag values 'd' into 'D' as recommended by 
'cif_core.dic' version 2.4.1. However, manual inspection revealed that the 
underlying problem was actually related to a bad tag order inside the 
atom site loop. The following changes were performed to resolve the problem:

* '_atom_site_refinement_flags' tag was changed into '_atom_site_calc_flag'.
  '_atom_site_calc_flag' was already present with all values set to '1' so 
  these values were removed (possible placeholder values for occupancies).
* there were two disordered hydrogen atoms with 'atom_site_disorder_assembly' 
  values 'PR'. The name of the disorder assembly also corresponded to 
  '_atom_site_refinement_flags_occupancy' and '_atom_site_refinement_flags_posn'
  tag values 'P' and 'R' so these tags were added into the loop.

For all changes the original paper was consulted.
;
_cod_original_cell_volume        1029.3(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2008276
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
F1 0.7729(3) -0.33908(12) 0.74169(10) 0.0775(5) Uani d . . 1 . . F
F2 0.8938(3) -0.35097(13) 0.94587(11) 0.0834(5) Uani d . . 1 . . F
F3 0.4844(3) -0.39132(12) 1.08263(12) 0.0702(4) Uani d . . 1 . . F
F4 0.6483(4) -0.53809(12) 1.15354(14) 0.0927(6) Uani d . . 1 . . F
F5 1.0612(4) -0.48252(14) 1.25217(14) 0.0956(6) Uani d . . 1 . . F
F6 1.3108(3) -0.27940(16) 1.28165(14) 0.0903(6) Uani d . . 1 . . F
F7 1.1503(2) -0.13294(13) 1.20844(15) 0.0793(5) Uani d . . 1 . . F
F8 0.7527(2) -0.13064(11) 1.33519(10) 0.0614(4) Uani d . . 1 . . F
F9 0.6012(3) 0.06618(12) 1.41872(9) 0.0641(4) Uani d . . 1 . . F
F10 0.0855(3) 0.12756(14) 1.35726(13) 0.0840(5) Uani d . . 1 . . F
F11 0.0607(3) 0.26211(16) 1.54248(13) 0.0887(5) Uani d . . 1 . . F
F12 0.4097(3) 0.42869(15) 1.63165(11) 0.0899(6) Uani d . . 1 . . F
F13 0.7807(3) 0.45872(15) 1.53611(13) 0.0954(6) Uani d . . 1 . . F
F14 0.8059(2) 0.32395(14) 1.35165(12) 0.0770(5) Uani d . . 1 . . F
C1 0.6242(4) -0.18424(16) 0.83843(16) 0.0424(5) Uani d . . 1 . . C
C2 0.7322(4) -0.27380(18) 0.82919(17) 0.0508(6) Uani d . . 1 . . C
C3 0.7864(4) -0.27982(19) 0.92257(18) 0.0546(6) Uani d . . 1 . . C
C4 0.7095(4) -0.19518(16) 0.99458(16) 0.0430(5) Uani d . . 1 . . C
C5 0.7268(3) -0.17777(16) 1.10102(15) 0.0408(5) Uani d . . 1 . . C
C6 0.6670(3) -0.09130(16) 1.17129(15) 0.0399(4) Uani d . . 1 . . C
C7 0.6819(4) -0.07033(17) 1.28057(15) 0.0432(5) Uani d . . 1 . . C
C8 0.6109(4) 0.02105(17) 1.31921(15) 0.0439(5) Uani d . . 1 . . C
C9 0.5468(3) 0.06112(16) 1.23643(15) 0.0394(4) Uani d . . 1 . . C
C10 0.4562(3) 0.15206(16) 1.24415(15) 0.0398(4) Uani d . . 1 . . C
C11 0.8140(3) -0.25825(16) 1.14288(15) 0.0414(5) Uani d . . 1 . . C
C12 0.6907(4) -0.36240(18) 1.13095(16) 0.0482(5) Uani d . . 1 . . C
C13 0.7730(5) -0.43804(18) 1.16599(18) 0.0575(6) Uani d . . 1 . . C
C14 0.9819(5) -0.4105(2) 1.21636(18) 0.0610(7) Uani d . . 1 . . C
C15 1.1075(4) -0.3075(2) 1.23030(19) 0.0583(6) Uani d . . 1 . . C
C16 1.0240(4) -0.23312(19) 1.19397(18) 0.0509(5) Uani d . . 1 . . C
C17 0.4452(3) 0.22206(16) 1.34958(15) 0.0405(5) Uani d . . 1 . . C
C18 0.2597(4) 0.20859(19) 1.40099(17) 0.0506(5) Uani d . . 1 . . C
C19 0.2466(4) 0.2769(2) 1.49576(18) 0.0565(6) Uani d . . 1 . . C
C20 0.4222(5) 0.3603(2) 1.54051(17) 0.0583(6) Uani d . . 1 . . C
C21 0.6102(4) 0.3758(2) 1.49261(18) 0.0590(6) Uani d . . 1 . . C
C22 0.6198(4) 0.30663(18) 1.39796(16) 0.0489(5) Uani d . . 1 . . C
N1 0.6157(3) -0.13761(13) 0.94028(12) 0.0419(4) Uani d . . 1 . . N
H1 0.5610 -0.0819 0.9657 0.050 Uiso calc P R 0.50 PR . H
N2 0.5844(3) -0.00948(13) 1.14789(12) 0.0398(4) Uani d . . 1 . . N
H2 0.5599 -0.0033 1.0872 0.050 Uiso calc P R 0.50 PR . H
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'
N N 0.0061 0.0033 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C1 . . 108.03(16) yes
C4 N1 H1 . . 126.0 no
C1 N1 H1 . . 126.0 no
C6 N2 C9 . . 109.41(16) yes
C6 N2 H2 . . 125.3 no
C9 N2 H2 . . 125.3 no
N1 C1 C10 . 2_657 127.11(18) yes
N1 C1 C2 . . 108.15(18) yes
C10 C1 C2 2_657 . 124.75(18) yes
C3 C2 F1 . . 125.9(2) no
C3 C2 C1 . . 108.06(19) yes
F1 C2 C1 . . 126.00(19) no
C2 C3 F2 . . 126.0(2) no
C2 C3 C4 . . 107.81(19) yes
F2 C3 C4 . . 126.2(2) no
N1 C4 C5 . . 126.86(18) yes
N1 C4 C3 . . 107.93(18) yes
C5 C4 C3 . . 125.21(19) yes
C6 C5 C4 . . 125.25(18) yes
C6 C5 C11 . . 117.22(18) no
C4 C5 C11 . . 117.53(17) no
N2 C6 C5 . . 125.87(18) yes
N2 C6 C7 . . 106.99(17) yes
C5 C6 C7 . . 127.13(18) yes
F8 C7 C8 . . 125.23(19) no
F8 C7 C6 . . 126.61(18) no
C8 C7 C6 . . 108.16(18) yes
C7 C8 F9 . . 125.24(19) no
C7 C8 C9 . . 108.49(18) yes
F9 C8 C9 . . 126.27(18) no
N2 C9 C10 . . 126.63(18) yes
N2 C9 C8 . . 106.94(17) yes
C10 C9 C8 . . 126.39(18) yes
C9 C10 C1 . 2_657 125.45(18) yes
C9 C10 C17 . . 117.30(18) no
C1 C10 C17 2_657 . 117.24(17) no
C16 C11 C12 . . 116.43(19) no
C16 C11 C5 . . 121.8(2) no
C12 C11 C5 . . 121.71(19) no
F3 C12 C13 . . 118.9(2) no
F3 C12 C11 . . 119.2(2) no
C13 C12 C11 . . 122.0(2) no
F4 C13 C12 . . 120.3(2) no
F4 C13 C14 . . 119.5(2) no
C12 C13 C14 . . 120.1(2) no
F5 C14 C15 . . 120.2(3) no
F5 C14 C13 . . 120.5(3) no
C15 C14 C13 . . 119.3(2) no
F6 C15 C16 . . 120.5(3) no
F6 C15 C14 . . 119.5(2) no
C16 C15 C14 . . 120.0(2) no
F7 C16 C15 . . 118.8(2) no
F7 C16 C11 . . 119.0(2) no
C15 C16 C11 . . 122.2(2) no
C18 C17 C22 . . 116.57(19) no
C18 C17 C10 . . 122.44(19) no
C22 C17 C10 . . 120.93(19) no
F10 C18 C17 . . 118.89(19) no
F10 C18 C19 . . 119.0(2) no
C17 C18 C19 . . 122.1(2) no
F11 C19 C20 . . 120.3(2) no
F11 C19 C18 . . 120.2(2) no
C20 C19 C18 . . 119.5(2) no
F12 C20 C19 . . 120.0(2) no
F12 C20 C21 . . 119.7(2) no
C19 C20 C21 . . 120.3(2) no
F13 C21 C20 . . 120.1(2) no
F13 C21 C22 . . 120.6(2) no
C20 C21 C22 . . 119.3(2) no
F14 C22 C17 . . 119.40(19) no
F14 C22 C21 . . 118.3(2) no
C17 C22 C21 . . 122.2(2) no
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
F1 C2 . 1.338(3) no
F2 C3 . 1.335(2) no
F3 C12 . 1.343(3) no
F4 C13 . 1.335(3) no
F5 C14 . 1.325(3) no
F6 C15 . 1.344(3) no
F7 C16 . 1.337(3) no
F8 C7 . 1.332(2) no
F9 C8 . 1.338(2) no
F10 C18 . 1.335(3) no
F11 C19 . 1.340(3) no
F12 C20 . 1.341(3) no
F13 C21 . 1.333(3) no
F14 C22 . 1.342(3) no
N1 C4 . 1.367(3) yes
N1 C1 . 1.369(3) yes
N1 H1 . 0.8600 no
N2 C6 . 1.370(2) yes
N2 C9 . 1.374(3) yes
N2 H2 . 0.8600 no
C1 C10 2_657 1.402(3) yes
C1 C2 . 1.438(3) yes
C2 C3 . 1.326(3) yes
C3 C4 . 1.447(3) yes
C4 C5 . 1.402(3) yes
C5 C6 . 1.400(3) yes
C5 C11 . 1.491(3) yes
C6 C7 . 1.436(3) yes
C7 C8 . 1.338(3) yes
C8 C9 . 1.431(3) yes
C9 C10 . 1.391(3) yes
C10 C1 2_657 1.402(3) no
C10 C17 . 1.500(3) no
C11 C16 . 1.382(3) no
C11 C12 . 1.378(3) no
C12 C13 . 1.371(3) no
C13 C14 . 1.369(4) no
C14 C15 . 1.366(4) no
C15 C16 . 1.370(3) no
C17 C18 . 1.374(3) no
C17 C22 . 1.374(3) no
C18 C19 . 1.380(3) no
C19 C20 . 1.360(4) no
C20 C21 . 1.362(4) no
C21 C22 . 1.378(3) no
