#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:15:05 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178943 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/72/4117201.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_4117201
loop_
_publ_author_name
'Daniel J. Nurco'
'Craig J. Medforth'
'Timothy P. Forsyth'
'Marilyn M. Olmstead'
'Kevin M. Smith'
_publ_contact_author
;
Dan Nurco, Chemistry Department, University of California, Davis, 95616 USA
;
_publ_contact_author_email       nurco@chem.ucdavis.edu
_publ_section_title
;
 Conformational Flexibility in Dodecasubstituted Porphyrins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10918
_journal_page_last               10919
_journal_paper_doi               10.1021/ja962164e
_journal_volume                  118
_journal_year                    1996
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C92 H34 F28 N4'
_chemical_formula_sum            'C92 H34 F28 N4'
_chemical_formula_weight         1727.23
_chemical_name_common            H₂F₂₈DPP
_chemical_name_systematic
; 
  5,10,15,20-tetrakis-(pentafluorophenyl)-2,3,7,8,12,13,17,18-octakis-(4- 
  fluorophenyl)-porphyrin
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 105.590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.6290(10)
_cell_length_b                   8.7210(10)
_cell_length_c                   25.700(3)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      29.9
_cell_measurement_theta_min      3.9
_cell_volume                     3589.9(6)
_computing_cell_refinement       'Siemens P3'
_computing_data_collection       'Siemens P3'
_computing_data_reduction        XDISK
_computing_molecular_graphics    XP
_computing_publication_material  XCIF
_computing_structure_refinement  'Siemens SHELXTL V. 5.03'
_computing_structure_solution    'Siemens SHELXTL V. 5.03'
_diffrn_ambient_temperature      130(2)
_diffrn_measurement_device       'Syntex P2₁'
_diffrn_measurement_method       'θ - 2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5639
_diffrn_reflns_theta_max         56.86
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        'no decay'
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.277
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   XABS2
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       needle
_exptl_crystal_F_000             1732
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.063
_refine_ls_goodness_of_fit_obs   1.145
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         4811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_restrained_S_obs      1.145
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_obs          0.0554
_refine_ls_shift/esd_max         -0.023
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0204P)²+3.7332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1087
_refine_ls_wR_factor_obs         0.0925
_reflns_number_observed          3203
_reflns_number_total             4811
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja962164e_2.cif
_cod_data_source_block           08xa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0204P)^2^+3.7332P] 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^)+(0.0204P)^2^+3.7332P] 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               4117201
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N -0.0479(2) 0.6641(4) 0.43947(13) 0.0144(8) Uani 1 d .
H1 H -0.0290(2) 0.5937(4) 0.46429(13) 0.017 Uiso 0.50 calc PR
C1 C -0.1279(2) 0.6712(5) 0.4060(2) 0.0137(10) Uani 1 d .
F1 F -0.3906(2) 1.0617(3) 0.20800(10) 0.0393(8) Uani 1 d .
N2 N 0.1169(2) 0.5961(4) 0.51685(13) 0.0164(9) Uani 1 d .
H2 H 0.0659(2) 0.5631(4) 0.51397(13) 0.020 Uiso 0.50 calc PR
C2 C -0.1334(2) 0.8060(5) 0.3719(2) 0.0151(10) Uani 1 d .
F2 F -0.0275(2) 1.4544(3) 0.29786(12) 0.0509(9) Uani 1 d .
C3 C -0.0580(2) 0.8786(5) 0.3867(2) 0.0135(10) Uani 1 d .
F3 F 0.1347(2) 1.0699(3) 0.50933(10) 0.0316(7) Uani 1 d .
C4 C -0.0025(2) 0.7849(5) 0.4278(2) 0.0130(10) Uani 1 d .
F4 F 0.1993(2) 1.3176(3) 0.47198(12) 0.0432(8) Uani 1 d .
C5 C 0.0839(2) 0.8030(5) 0.4485(2) 0.0152(10) Uani 1 d .
F5 F 0.2222(2) 1.3146(3) 0.37213(12) 0.0484(9) Uani 1 d .
C6 C 0.1395(3) 0.7092(5) 0.4862(2) 0.0149(10) Uani 1 d .
F6 F 0.1823(2) 1.0607(4) 0.30883(11) 0.0488(9) Uani 1 d .
C7 C 0.2302(2) 0.7209(5) 0.5005(2) 0.0160(10) Uani 1 d .
F7 F 0.1147(2) 0.8160(3) 0.34529(10) 0.0329(7) Uani 1 d .
C8 C 0.2599(2) 0.6225(5) 0.5421(2) 0.0142(10) Uani 1 d .
F8 F 0.4493(2) 0.9982(4) 0.39758(14) 0.0651(11) Uani 1 d .
C9 C 0.1887(2) 0.5439(5) 0.5528(2) 0.0139(10) Uani 1 d .
F9 F 0.60732(14) 0.5554(4) 0.60517(11) 0.0403(8) Uani 1 d .
C10 C 0.1924(2) 0.4294(5) 0.5912(2) 0.0150(10) Uani 1 d .
F10 F 0.2287(2) 0.6067(3) 0.68459(10) 0.0316(7) Uani 1 d .
F11 F 0.3673(2) 0.5788(4) 0.76687(11) 0.0456(9) Uani 1 d .
F12 F 0.4844(2) 0.3669(4) 0.76185(11) 0.0478(9) Uani 1 d .
F13 F 0.4631(2) 0.1881(3) 0.67235(11) 0.0428(8) Uani 1 d .
F14 F 0.32325(15) 0.2140(3) 0.59056(10) 0.0272(7) Uani 1 d .
C2A C -0.2052(2) 0.8684(5) 0.3291(2) 0.0140(10) Uani 1 d .
C2B C -0.2475(2) 0.9977(5) 0.3394(2) 0.0192(11) Uani 1 d .
H2B H -0.2335(2) 1.0420(5) 0.3744(2) 0.023 Uiso 1 calc R
C2C C -0.3108(3) 1.0621(6) 0.2979(2) 0.0229(11) Uani 1 d .
H2C H -0.3408(3) 1.1494(6) 0.3044(2) 0.028 Uiso 1 calc R
C2D C -0.3283(3) 0.9971(6) 0.2481(2) 0.0251(12) Uani 1 d .
C2E C -0.2879(3) 0.8709(5) 0.2359(2) 0.0230(11) Uani 1 d .
H2E H -0.3020(3) 0.8289(5) 0.2005(2) 0.028 Uiso 1 calc R
C2F C -0.2252(2) 0.8066(5) 0.2774(2) 0.0175(10) Uani 1 d .
H2F H -0.1957(2) 0.7193(5) 0.2702(2) 0.021 Uiso 1 calc R
C3A C -0.0440(2) 1.0309(5) 0.3642(2) 0.0166(11) Uani 1 d .
C3B C -0.0372(3) 1.1629(5) 0.3953(2) 0.0209(11) Uani 1 d .
H3B H -0.0366(3) 1.1550(5) 0.4323(2) 0.025 Uiso 1 calc R
C3C C -0.0314(3) 1.3058(5) 0.3732(2) 0.0282(12) Uani 1 d .
H3C H -0.0265(3) 1.3963(5) 0.3945(2) 0.034 Uiso 1 calc R
C3D C -0.0328(3) 1.3128(6) 0.3192(2) 0.0290(12) Uani 1 d .
C3E C -0.0405(3) 1.1875(6) 0.2867(2) 0.0297(13) Uani 1 d .
H3E H -0.0415(3) 1.1967(6) 0.2497(2) 0.036 Uiso 1 calc R
C3F C -0.0468(3) 1.0446(5) 0.3099(2) 0.0210(11) Uani 1 d .
H3F H -0.0531(3) 0.9551(5) 0.2881(2) 0.025 Uiso 1 calc R
C5A C 0.1221(2) 0.9365(5) 0.4279(2) 0.0154(10) Uani 1 d .
C5B C 0.1451(3) 1.0660(5) 0.4589(2) 0.0179(11) Uani 1 d .
C5C C 0.1784(3) 1.1924(5) 0.4412(2) 0.0244(11) Uani 1 d .
C5D C 0.1905(3) 1.1922(6) 0.3903(2) 0.0272(12) Uani 1 d .
C5E C 0.1696(3) 1.0643(6) 0.3584(2) 0.0254(12) Uani 1 d .
C5F C 0.1356(3) 0.9394(5) 0.3770(2) 0.0199(11) Uani 1 d .
C7A C 0.2858(2) 0.8017(5) 0.4724(2) 0.0169(10) Uani 1 d .
C7B C 0.3317(3) 0.9290(5) 0.4944(2) 0.0239(11) Uani 1 d .
H7B H 0.3256(3) 0.9709(5) 0.5272(2) 0.029 Uiso 1 calc R
C7C C 0.3865(3) 0.9964(6) 0.4692(2) 0.0338(13) Uani 1 d .
H7C H 0.4181(3) 1.0841(6) 0.4843(2) 0.041 Uiso 1 calc R
C7D C 0.3940(3) 0.9341(7) 0.4223(2) 0.0378(14) Uani 1 d .
C7E C 0.3514(3) 0.8077(6) 0.3991(2) 0.0345(13) Uani 1 d .
H7E H 0.3591(3) 0.7659(6) 0.3667(2) 0.041 Uiso 1 calc R
C7F C 0.2962(3) 0.7420(5) 0.4246(2) 0.0238(12) Uani 1 d .
H7F H 0.2649(3) 0.6545(5) 0.4090(2) 0.029 Uiso 1 calc R
C8A C 0.3516(2) 0.5934(5) 0.5642(2) 0.0157(10) Uani 1 d .
C8B C 0.4012(3) 0.6902(6) 0.6025(2) 0.0227(11) Uani 1 d .
H8B H 0.3757(3) 0.7675(6) 0.6187(2) 0.027 Uiso 1 calc R
C8C C 0.4871(3) 0.6755(6) 0.6173(2) 0.0279(12) Uani 1 d .
H8C H 0.5210(3) 0.7416(6) 0.6436(2) 0.033 Uiso 1 calc R
C8D C 0.5223(3) 0.5639(6) 0.5932(2) 0.0272(12) Uani 1 d .
C8E C 0.4759(3) 0.4642(6) 0.5563(2) 0.0250(12) Uani 1 d .
H8E H 0.5021(3) 0.3854(6) 0.5412(2) 0.030 Uiso 1 calc R
C8F C 0.3904(3) 0.4799(5) 0.5413(2) 0.0228(12) Uani 1 d .
H8F H 0.3573(3) 0.4126(5) 0.5150(2) 0.027 Uiso 1 calc R
C10A C 0.2728(3) 0.4132(5) 0.6346(2) 0.0174(11) Uani 1 d .
C10B C 0.2872(3) 0.5048(5) 0.6804(2) 0.0189(11) Uani 1 d .
C10C C 0.3576(3) 0.4919(6) 0.7226(2) 0.0258(12) Uani 1 d .
C10D C 0.4164(3) 0.3856(6) 0.7202(2) 0.0294(13) Uani 1 d .
C10E C 0.4061(3) 0.2946(6) 0.6749(2) 0.0273(12) Uani 1 d .
C10F C 0.3341(3) 0.3086(5) 0.6336(2) 0.0202(11) Uani 1 d .
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'
N N 0.0311 0.0180 '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'
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
C4 N1 C1 108.9(3) . .
N1 C1 C10 124.2(4) . 3_566
N1 C1 C2 107.9(4) . .
C10 C1 C2 127.7(4) 3_566 .
C6 N2 C9 107.5(3) . .
C3 C2 C1 107.6(4) . .
C3 C2 C2A 122.0(4) . .
C1 C2 C2A 130.3(4) . .
C2 C3 C4 107.4(4) . .
C2 C3 C3A 122.2(4) . .
C4 C3 C3A 130.3(4) . .
N1 C4 C5 124.7(4) . .
N1 C4 C3 108.1(3) . .
C5 C4 C3 126.9(4) . .
C6 C5 C4 127.8(4) . .
C6 C5 C5A 115.8(4) . .
C4 C5 C5A 116.4(4) . .
N2 C6 C5 125.5(4) . .
N2 C6 C7 109.3(4) . .
C5 C6 C7 125.2(4) . .
C8 C7 C6 106.6(4) . .
C8 C7 C7A 122.6(4) . .
C6 C7 C7A 130.2(4) . .
C7 C8 C9 107.8(4) . .
C7 C8 C8A 121.6(4) . .
C9 C8 C8A 130.0(4) . .
N2 C9 C10 125.3(4) . .
N2 C9 C8 108.6(4) . .
C10 C9 C8 126.1(4) . .
C9 C10 C1 126.6(4) . 3_566
C9 C10 C10A 117.0(4) . .
C1 C10 C10A 116.3(4) 3_566 .
C2F C2A C2B 119.6(4) . .
C2F C2A C2 120.1(4) . .
C2B C2A C2 120.0(4) . .
C2A C2B C2C 119.7(4) . .
C2D C2C C2B 118.5(4) . .
F1 C2D C2C 117.6(4) . .
F1 C2D C2E 118.5(4) . .
C2C C2D C2E 123.9(4) . .
C2D C2E C2F 117.4(4) . .
C2A C2F C2E 120.9(4) . .
C3F C3A C3B 118.9(4) . .
C3F C3A C3 120.0(4) . .
C3B C3A C3 120.8(4) . .
C3A C3B C3C 120.9(4) . .
C3D C3C C3B 117.9(5) . .
F2 C3D C3E 119.0(4) . .
F2 C3D C3C 117.3(5) . .
C3E C3D C3C 123.7(5) . .
C3D C3E C3F 117.3(4) . .
C3A C3F C3E 121.3(4) . .
C5B C5A C5F 116.1(4) . .
C5B C5A C5 121.0(4) . .
C5F C5A C5 122.9(4) . .
F3 C5B C5C 117.8(4) . .
F3 C5B C5A 119.1(4) . .
C5C C5B C5A 123.0(4) . .
F4 C5C C5B 121.7(4) . .
F4 C5C C5D 118.8(4) . .
C5B C5C C5D 119.4(5) . .
F5 C5D C5E 120.2(4) . .
F5 C5D C5C 120.3(5) . .
C5E C5D C5C 119.4(4) . .
F6 C5E C5F 119.8(4) . .
F6 C5E C5D 120.4(4) . .
C5F C5E C5D 119.9(4) . .
F7 C5F C5E 119.3(4) . .
F7 C5F C5A 118.6(4) . .
C5E C5F C5A 122.1(4) . .
C7B C7A C7F 118.5(4) . .
C7B C7A C7 121.9(4) . .
C7F C7A C7 119.4(4) . .
C7A C7B C7C 120.8(5) . .
C7D C7C C7B 118.4(5) . .
C7C C7D C7E 123.5(5) . .
C7C C7D F8 118.8(5) . .
C7E C7D F8 117.7(5) . .
C7D C7E C7F 117.5(5) . .
C7A C7F C7E 121.3(5) . .
C8B C8A C8F 118.5(4) . .
C8B C8A C8 121.1(4) . .
C8F C8A C8 119.8(4) . .
C8C C8B C8A 120.8(4) . .
C8D C8C C8B 118.6(4) . .
C8E C8D F9 118.7(4) . .
C8E C8D C8C 122.6(4) . .
F9 C8D C8C 118.6(4) . .
C8D C8E C8F 118.7(4) . .
C8E C8F C8A 120.8(4) . .
C10F C10A C10B 116.0(4) . .
C10F C10A C10 124.5(4) . .
C10B C10A C10 119.5(4) . .
F10 C10B C10C 118.2(4) . .
F10 C10B C10A 119.1(4) . .
C10C C10B C10A 122.7(4) . .
F11 C10C C10B 120.6(4) . .
F11 C10C C10D 120.0(4) . .
C10B C10C C10D 119.4(4) . .
F12 C10D C10C 120.5(5) . .
F12 C10D C10E 119.3(5) . .
C10C C10D C10E 120.2(4) . .
F13 C10E C10F 120.2(5) . .
F13 C10E C10D 120.7(4) . .
C10F C10E C10D 119.0(4) . .
F14 C10F C10E 118.3(4) . .
F14 C10F C10A 119.0(4) . .
C10E C10F C10A 122.7(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.376(5) .
N1 C1 1.378(5) .
C1 C10 1.403(6) 3_566
C1 C2 1.454(6) .
F1 C2D 1.371(5) .
N2 C6 1.376(5) .
N2 C9 1.377(5) .
C2 C3 1.364(6) .
C2 C2A 1.493(5) .
F2 C3D 1.364(5) .
C3 C4 1.453(5) .
C3 C3A 1.491(6) .
F3 C5B 1.354(4) .
C4 C5 1.401(5) .
F4 C5C 1.338(5) .
C5 C6 1.407(6) .
C5 C5A 1.490(6) .
F5 C5D 1.330(5) .
C6 C7 1.458(5) .
F6 C5E 1.346(5) .
C7 C8 1.355(6) .
C7 C7A 1.493(6) .
F7 C5F 1.339(5) .
C8 C9 1.457(5) .
C8 C8A 1.500(5) .
F8 C7D 1.369(5) .
C9 C10 1.392(6) .
F9 C8D 1.366(5) .
C10 C1 1.403(6) 3_566
C10 C10A 1.500(5) .
F10 C10B 1.344(5) .
F11 C10C 1.340(5) .
F12 C10D 1.343(5) .
F13 C10E 1.342(5) .
F14 C10F 1.352(5) .
C2A C2F 1.388(5) .
C2A C2B 1.392(6) .
C2B C2C 1.398(6) .
C2C C2D 1.358(6) .
C2D C2E 1.368(6) .
C2E C2F 1.394(6) .
C3A C3F 1.388(6) .
C3A C3B 1.390(6) .
C3B C3C 1.384(6) .
C3C C3D 1.383(6) .
C3D C3E 1.361(7) .
C3E C3F 1.398(6) .
C5A C5B 1.375(6) .
C5A C5F 1.386(6) .
C5B C5C 1.365(6) .
C5C C5D 1.376(6) .
C5D C5E 1.372(6) .
C5E C5F 1.371(6) .
C7A C7B 1.379(6) .
C7A C7F 1.388(6) .
C7B C7C 1.383(6) .
C7C C7D 1.358(7) .
C7D C7E 1.358(7) .
C7E C7F 1.387(6) .
C8A C8B 1.386(6) .
C8A C8F 1.396(6) .
C8B C8C 1.383(6) .
C8C C8D 1.366(7) .
C8D C8E 1.362(6) .
C8E C8F 1.377(6) .
C10A C10F 1.372(6) .
C10A C10B 1.388(6) .
C10B C10C 1.371(6) .
C10C C10D 1.360(6) .
C10D C10E 1.380(7) .
C10E C10F 1.376(6) .
