#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/72/1507280.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_1507280
loop_
_publ_author_name
'Maeda, Hiromitsu'
'Osuka, Atsuhiro'
'Ishikawa, Yuichi'
'Aritome, Isao'
'Hisaeda, Yoshio'
'Furuta, Hiroyuki'
_publ_section_title
;
 N-confused porphyrin-bearing meso-perfluorophenyl groups: a potential
 agent that forms stable square-planar complexes with Cu(II) and Ag(III).
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1293
_journal_page_last               1296
_journal_paper_doi               10.1021/ol034227l
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C44 H8 F20 N4 Ni'
_chemical_formula_weight         1031.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   19.6856(10)
_cell_length_b                   19.6856(10)
_cell_length_c                   24.831(3)
_cell_measurement_reflns_used    3769
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      2.46
_cell_volume                     8333.4(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16777
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.7997
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4572
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0791P)²+13.1851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1492
_reflns_number_gt                2349
_reflns_number_total             3516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034227lsi20030207_112228.cif
_cod_data_source_block           C6F5-NCP-Ni(II)_(4-Ni)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Rhombohedral' changed to
'rhombohedral' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        8333.5(11)
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               1507280
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7672(2) 0.0172(2) 0.10278(15) 0.0383(8) Uani 1 1 d .
C2 C 0.7204(2) -0.0188(2) 0.05649(16) 0.0443(9) Uani 1 1 d .
H2 H 0.7064 -0.0692 0.0427 0.053 Uiso 1 1 calc R
C3 C 0.6998(2) 0.0302(2) 0.03621(15) 0.0409(9) Uani 1 1 d .
H3 H 0.6681 0.0213 0.0053 0.049 Uiso 1 1 calc R
C4 C 0.7337(2) 0.0991(2) 0.06898(14) 0.0385(8) Uani 1 1 d .
C5 C 0.7235(2) 0.1625(2) 0.05921(15) 0.0388(8) Uani 1 1 d .
C6 C 0.7574(2) 0.2281(2) 0.09128(15) 0.0379(8) Uani 1 1 d .
C7 C 0.7490(2) 0.2955(2) 0.08205(16) 0.0431(9) Uani 1 1 d .
H7 H 0.7209 0.3022 0.0534 0.052 Uiso 1 1 calc R
C8 C 0.7880(2) 0.3471(2) 0.12136(16) 0.0435(9) Uani 1 1 d .
H8 H 0.7926 0.3971 0.1259 0.052 Uiso 1 1 calc R
C9 C 0.8213(2) 0.3128(2) 0.15504(16) 0.0392(8) Uani 1 1 d .
C10 C 0.8671(2) 0.3506(2) 0.19898(16) 0.0412(9) Uani 1 1 d .
C11 C 0.6723(2) 0.1583(2) 0.01332(16) 0.0427(9) Uani 1 1 d .
C12 C 0.7021(3) 0.1971(3) -0.03433(17) 0.0551(11) Uani 1 1 d .
C13 C 0.6533(3) 0.1942(3) -0.07605(19) 0.0700(13) Uani 1 1 d .
C14 C 0.5740(3) 0.1507(3) -0.0694(2) 0.0696(14) Uani 1 1 d .
C15 C 0.5433(3) 0.1119(2) -0.0227(2) 0.0642(13) Uani 1 1 d .
C16 C 0.5917(2) 0.1150(2) 0.01805(18) 0.0490(10) Uani 1 1 d .
C17 C 0.8828(2) 0.4310(2) 0.21363(16) 0.0451(9) Uani 1 1 d .
C18 C 0.9509(3) 0.4976(2) 0.19810(18) 0.0542(11) Uani 1 1 d .
C19 C 0.9674(3) 0.5718(2) 0.21324(19) 0.0592(12) Uani 1 1 d .
C20 C 0.9145(3) 0.5795(2) 0.24491(19) 0.0586(13) Uani 1 1 d .
C21 C 0.8458(3) 0.5151(3) 0.26078(19) 0.0553(11) Uani 1 1 d .
C22 C 0.8304(2) 0.4415(2) 0.24482(18) 0.0493(10) Uani 1 1 d .
F1 F 0.77990(17) 0.2396(2) -0.04157(11) 0.0814(9) Uani 1 1 d .
F2 F 0.6850(2) 0.2345(3) -0.12146(12) 0.1085(12) Uani 1 1 d .
F3 F 0.5260(2) 0.1468(2) -0.10944(13) 0.0991(11) Uani 1 1 d .
F4 F 0.46535(16) 0.07048(17) -0.01592(16) 0.0970(11) Uani 1 1 d .
F5 F 0.55934(14) 0.07507(14) 0.06343(11) 0.0642(7) Uani 1 1 d .
F6 F 1.00372(16) 0.49054(15) 0.16831(12) 0.0743(8) Uani 1 1 d .
F7 F 1.03431(17) 0.63502(15) 0.19828(13) 0.0849(9) Uani 1 1 d .
F8 F 0.93087(18) 0.65157(14) 0.26103(12) 0.0794(9) Uani 1 1 d .
F9 F 0.79483(17) 0.52319(16) 0.29165(12) 0.0746(8) Uani 1 1 d .
F10 F 0.76471(14) 0.37937(14) 0.26167(12) 0.0635(7) Uani 1 1 d .
N1 N 0.77545(18) 0.09127(18) 0.11075(13) 0.0428(8) Uani 1 1 d .
N2 N 0.80264(17) 0.23918(17) 0.13657(12) 0.0378(7) Uani 1 1 d .
Ni1 Ni 0.8333 0.1667 0.1667 0.0331(2) Uani 1 2 d S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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
C10 C1 N1 126.1(3) 13_655 .
C10 C1 C2 123.8(3) 13_655 .
N1 C1 C2 110.1(3) . .
C3 C2 C1 107.6(3) . .
C3 C2 H2 126.2 . .
C1 C2 H2 126.2 . .
C2 C3 C4 108.0(3) . .
C2 C3 H3 126.0 . .
C4 C3 H3 126.0 . .
N1 C4 C5 126.7(3) . .
N1 C4 C3 110.1(3) . .
C5 C4 C3 123.2(3) . .
C6 C5 C4 121.7(3) . .
C6 C5 C11 119.4(3) . .
C4 C5 C11 118.8(3) . .
C5 C6 N2 126.3(3) . .
C5 C6 C7 123.4(3) . .
N2 C6 C7 110.3(3) . .
C8 C7 C6 107.3(3) . .
C8 C7 H7 126.4 . .
C6 C7 H7 126.4 . .
C7 C8 C9 107.1(3) . .
C7 C8 H8 126.5 . .
C9 C8 H8 126.5 . .
C10 C9 N2 126.1(3) . .
C10 C9 C8 122.9(3) . .
N2 C9 C8 111.0(3) . .
C9 C10 C1 121.5(3) . 13_655
C9 C10 C17 119.9(3) . .
C1 C10 C17 118.6(3) 13_655 .
C12 C11 C16 117.2(4) . .
C12 C11 C5 122.6(4) . .
C16 C11 C5 120.3(4) . .
F1 C12 C11 120.0(4) . .
F1 C12 C13 118.3(4) . .
C11 C12 C13 121.7(4) . .
F2 C13 C14 121.4(5) . .
F2 C13 C12 119.6(5) . .
C14 C13 C12 119.0(5) . .
F3 C14 C15 119.8(5) . .
F3 C14 C13 119.8(5) . .
C15 C14 C13 120.3(4) . .
F4 C15 C14 120.2(4) . .
F4 C15 C16 119.6(5) . .
C14 C15 C16 120.2(5) . .
F5 C16 C15 118.6(4) . .
F5 C16 C11 119.8(4) . .
C15 C16 C11 121.6(4) . .
C18 C17 C22 117.1(4) . .
C18 C17 C10 121.7(4) . .
C22 C17 C10 121.2(3) . .
F6 C18 C19 118.4(4) . .
F6 C18 C17 119.4(4) . .
C19 C18 C17 122.1(4) . .
F7 C19 C20 120.4(4) . .
F7 C19 C18 120.8(5) . .
C20 C19 C18 118.8(4) . .
F8 C20 C21 119.5(5) . .
F8 C20 C19 119.4(4) . .
C21 C20 C19 121.1(4) . .
F9 C21 C20 120.6(4) . .
F9 C21 C22 120.4(4) . .
C20 C21 C22 118.9(4) . .
F10 C22 C21 118.5(4) . .
F10 C22 C17 119.6(3) . .
C21 C22 C17 121.9(4) . .
C4 N1 C1 104.2(3) . .
C4 N1 Ni1 127.6(2) . .
C1 N1 Ni1 128.2(3) . .
C6 N2 C9 104.3(3) . .
C6 N2 Ni1 127.3(2) . .
C9 N2 Ni1 128.4(2) . .
N1 Ni1 N1 179.997(1) . 13_655
N1 Ni1 N2 89.58(13) . 13_655
N1 Ni1 N2 90.42(13) 13_655 13_655
N1 Ni1 N2 90.42(13) . .
N1 Ni1 N2 89.58(13) 13_655 .
N2 Ni1 N2 180.0 13_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C10 1.383(5) 13_655
C1 N1 1.398(5) .
C1 C2 1.421(5) .
C2 C3 1.319(5) .
C2 H2 0.9500 .
C3 C4 1.429(5) .
C3 H3 0.9500 .
C4 N1 1.379(5) .
C4 C5 1.381(5) .
C5 C6 1.374(5) .
C5 C11 1.495(5) .
C6 N2 1.382(5) .
C6 C7 1.434(5) .
C7 C8 1.340(5) .
C7 H7 0.9500 .
C8 C9 1.423(5) .
C8 H8 0.9500 .
C9 C10 1.374(5) .
C9 N2 1.383(5) .
C10 C1 1.383(5) 13_655
C10 C17 1.498(5) .
C11 C12 1.371(6) .
C11 C16 1.381(5) .
C12 F1 1.341(5) .
C12 C13 1.394(6) .
C13 F2 1.340(6) .
C13 C14 1.364(7) .
C14 F3 1.346(5) .
C14 C15 1.354(8) .
C15 F4 1.341(5) .
C15 C16 1.370(6) .
C16 F5 1.339(5) .
C17 C18 1.381(6) .
C17 C22 1.385(6) .
C18 F6 1.339(5) .
C18 C19 1.381(6) .
C19 F7 1.334(5) .
C19 C20 1.373(7) .
C20 F8 1.349(5) .
C20 C21 1.370(7) .
C21 F9 1.333(5) .
C21 C22 1.382(6) .
C22 F10 1.328(5) .
N1 Ni1 1.933(3) .
N2 Ni1 1.955(3) .
Ni1 N1 1.933(3) 13_655
Ni1 N2 1.955(3) 13_655
