#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/60/1506043.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_1506043
loop_
_publ_author_name
'Samaroo, Diana'
'Soll, Clifford E.'
'Todaro, Louis J.'
'Drain, Charles M.'
_publ_section_title
;
 Efficient microwave-assisted synthesis of amine-substituted
 tetrakis(pentafluorophenyl)porphyrin.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4985
_journal_page_last               4988
_journal_paper_doi               10.1021/ol060946z
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C39.5 H39 F8 N6 O4'
_chemical_formula_weight         813.77
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.03(3)
_cell_angle_beta                 104.31(3)
_cell_angle_gamma                107.76(3)
_cell_formula_units_Z            2
_cell_length_a                   10.750(2)
_cell_length_b                   10.912(2)
_cell_length_c                   17.685(4)
_cell_measurement_temperature    373(2)
_cell_volume                     1904.5(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      373(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'ω 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    0.0772
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16118
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         8724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0680
_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)+(0.0465P)²+1.9897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                5349
_reflns_number_total             8724
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060946zsi20060419_020047.cif
_cod_data_source_block           x1536l
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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        1904.5(7)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C39.50 H39 F8 N6 O4'
_cod_database_code               1506043
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F -0.03082(17) 0.19835(16) 0.21473(10) 0.0359(4) Uani 1 1 d .
F2 F 0.01866(17) 0.23475(15) 0.07525(9) 0.0366(4) Uani 1 1 d .
F3 F 0.34405(17) 0.01706(16) 0.13928(10) 0.0383(4) Uani 1 1 d .
F4 F 0.29404(16) -0.01823(15) 0.27675(9) 0.0326(4) Uani 1 1 d .
F5 F 0.44093(17) 0.45515(15) 0.62223(11) 0.0395(4) Uani 1 1 d .
F6 F 0.54485(17) 0.70403(15) 0.68072(11) 0.0407(4) Uani 1 1 d .
F7 F 0.10395(17) 0.73375(15) 0.63229(10) 0.0390(4) Uani 1 1 d .
F8 F 0.00113(16) 0.48473(14) 0.58111(10) 0.0333(4) Uani 1 1 d .
O19 O 0.1562(2) 0.32684(19) -0.08377(12) 0.0373(5) Uani 1 1 d .
O20 O 0.3419(2) 0.44316(18) -0.12233(12) 0.0344(5) Uani 1 1 d .
O39 O 0.5030(2) 1.21789(18) 0.81276(12) 0.0375(5) Uani 1 1 d .
O40 O 0.6313(2) 1.28485(18) 0.72698(12) 0.0371(5) Uani 1 1 d .
N1 N -0.0204(2) -0.1079(2) 0.40111(13) 0.0241(5) Uani 1 1 d .
H1A H -0.0064 -0.0623 0.4444 0.029 Uiso 0.25 1 calc PR
N2 N 0.1116(2) 0.1626(2) 0.45711(13) 0.0239(5) Uani 1 1 d .
H2A H 0.0688 0.0946 0.4753 0.029 Uiso 0.75 1 calc PR
N5 N 0.1984(3) 0.1454(2) 0.02730(14) 0.0347(6) Uani 1 1 d .
H5A H 0.1741 0.2069 0.0050 0.042 Uiso 1 1 calc R
N6 N 0.3062(3) 0.2357(2) -0.11021(14) 0.0337(6) Uani 1 1 d .
H6A H 0.3832 0.2505 -0.1207 0.040 Uiso 1 1 calc R
N7 N 0.3896(3) 0.8542(2) 0.69047(16) 0.0371(6) Uani 1 1 d .
H7A H 0.4671 0.8940 0.6826 0.044 Uiso 1 1 calc R
N8 N 0.4322(3) 1.1329(2) 0.68565(15) 0.0370(6) Uani 1 1 d .
H8A H 0.4496 1.1367 0.6406 0.044 Uiso 1 1 calc R
C1 C -0.0900(3) -0.2372(2) 0.38210(16) 0.0247(6) Uani 1 1 d .
C2 C -0.0920(3) -0.2775(2) 0.30374(15) 0.0266(6) Uani 1 1 d .
H2B H -0.1338 -0.3602 0.2777 0.032 Uiso 1 1 calc R
C3 C -0.0223(3) -0.1732(2) 0.27561(16) 0.0284(6) Uani 1 1 d .
H3A H -0.0054 -0.1697 0.2264 0.034 Uiso 1 1 calc R
C4 C 0.0219(3) -0.0669(2) 0.33635(16) 0.0244(6) Uani 1 1 d .
C5 C 0.0951(3) 0.0601(2) 0.32797(15) 0.0235(6) Uani 1 1 d .
C6 C 0.1373(3) 0.1658(2) 0.38486(16) 0.0248(6) Uani 1 1 d .
C7 C 0.2127(3) 0.2961(2) 0.37871(16) 0.0267(6) Uani 1 1 d .
H7B H 0.2451 0.3265 0.3362 0.032 Uiso 1 1 calc R
C8 C 0.2287(3) 0.3676(2) 0.44567(16) 0.0276(6) Uani 1 1 d .
H8B H 0.2738 0.4559 0.4572 0.033 Uiso 1 1 calc R
C9 C 0.1645(3) 0.2844(2) 0.49564(16) 0.0254(6) Uani 1 1 d .
C10 C 0.1550(3) 0.3198(2) 0.56976(16) 0.0247(6) Uani 1 1 d .
C11 C 0.1283(3) 0.0862(2) 0.25147(16) 0.0239(6) Uani 1 1 d .
C12 C 0.0634(3) 0.1528(2) 0.19756(16) 0.0261(6) Uani 1 1 d .
C13 C 0.0876(3) 0.1708(2) 0.12558(16) 0.0276(6) Uani 1 1 d .
C14 C 0.1796(3) 0.1246(2) 0.10007(16) 0.0279(6) Uani 1 1 d .
C15 C 0.2468(3) 0.0606(3) 0.15492(17) 0.0277(6) Uani 1 1 d .
C16 C 0.2216(3) 0.0428(2) 0.22759(16) 0.0264(6) Uani 1 1 d .
C17 C 0.2561(3) 0.0725(3) -0.01557(17) 0.0348(7) Uani 1 1 d .
H17A H 0.2149 -0.0193 -0.0135 0.042 Uiso 1 1 calc R
H17B H 0.3527 0.0949 0.0082 0.042 Uiso 1 1 calc R
C18 C 0.2311(3) 0.1034(3) -0.10033(17) 0.0365(7) Uani 1 1 d .
H18A H 0.2560 0.0439 -0.1304 0.044 Uiso 1 1 calc R
H18B H 0.1350 0.0894 -0.1216 0.044 Uiso 1 1 calc R
C19 C 0.2591(3) 0.3346(3) -0.10349(17) 0.0324(7) Uani 1 1 d .
C20 C 0.3318(3) 0.5714(3) -0.10254(18) 0.0362(7) Uani 1 1 d .
C21 C 0.2020(4) 0.5850(3) -0.1526(2) 0.0449(8) Uani 1 1 d .
H21A H 0.1263 0.5270 -0.1382 0.067 Uiso 1 1 calc R
H21B H 0.1948 0.5644 -0.2068 0.067 Uiso 1 1 calc R
H21C H 0.2023 0.6724 -0.1446 0.067 Uiso 1 1 calc R
C22 C 0.3437(4) 0.5912(3) -0.01594(19) 0.0468(9) Uani 1 1 d .
H22A H 0.2654 0.5329 -0.0041 0.070 Uiso 1 1 calc R
H22B H 0.3496 0.6787 -0.0023 0.070 Uiso 1 1 calc R
H22C H 0.4236 0.5745 0.0136 0.070 Uiso 1 1 calc R
C23 C 0.4531(4) 0.6617(3) -0.1237(2) 0.0455(8) Uani 1 1 d .
H23A H 0.4428 0.6474 -0.1789 0.068 Uiso 1 1 calc R
H23B H 0.5339 0.6454 -0.0950 0.068 Uiso 1 1 calc R
H23C H 0.4598 0.7497 -0.1106 0.068 Uiso 1 1 calc R
C31 C 0.2167(3) 0.4604(2) 0.59943(15) 0.0252(6) Uani 1 1 d .
C32 C 0.3551(3) 0.5216(3) 0.62453(16) 0.0280(6) Uani 1 1 d .
C33 C 0.4087(3) 0.6501(3) 0.65455(17) 0.0292(6) Uani 1 1 d .
C34 C 0.3289(3) 0.7266(2) 0.66062(16) 0.0279(6) Uani 1 1 d .
C35 C 0.1901(3) 0.6659(3) 0.63318(16) 0.0278(6) Uani 1 1 d .
C36 C 0.1372(3) 0.5367(2) 0.60507(16) 0.0256(6) Uani 1 1 d .
C37 C 0.3324(3) 0.9265(3) 0.73435(18) 0.0344(7) Uani 1 1 d .
H37A H 0.3939 0.9571 0.7861 0.041 Uiso 1 1 calc R
H37B H 0.2474 0.8697 0.7409 0.041 Uiso 1 1 calc R
C38 C 0.3078(3) 1.0407(3) 0.69336(19) 0.0375(7) Uani 1 1 d .
H38A H 0.2462 1.0101 0.6417 0.045 Uiso 1 1 calc R
H38B H 0.2651 1.0835 0.7229 0.045 Uiso 1 1 calc R
C39 C 0.5214(3) 1.2129(3) 0.74739(18) 0.0328(7) Uani 1 1 d .
C40 C 0.7414(3) 1.3837(3) 0.78398(19) 0.0378(7) Uani 1 1 d .
C41 C 0.8062(3) 1.3206(3) 0.8513(2) 0.0454(8) Uani 1 1 d .
H41A H 0.8383 1.2572 0.8312 0.068 Uiso 1 1 calc R
H41B H 0.7405 1.2794 0.8788 0.068 Uiso 1 1 calc R
H41C H 0.8809 1.3852 0.8866 0.068 Uiso 1 1 calc R
C42 C 0.6875(4) 1.4859(3) 0.8106(2) 0.0434(8) Uani 1 1 d .
H42A H 0.6479 1.5228 0.7658 0.065 Uiso 1 1 calc R
H42B H 0.7605 1.5526 0.8455 0.065 Uiso 1 1 calc R
H42C H 0.6200 1.4469 0.8374 0.065 Uiso 1 1 calc R
C43 C 0.8372(4) 1.4390(3) 0.7342(2) 0.0498(9) Uani 1 1 d .
H43A H 0.8699 1.3730 0.7179 0.075 Uiso 1 1 calc R
H43B H 0.9122 1.5096 0.7642 0.075 Uiso 1 1 calc R
H43C H 0.7901 1.4694 0.6888 0.075 Uiso 1 1 calc R
C51 C 0.407(2) 0.047(2) 0.4852(9) 0.043(3) Uani 0.50 1 d P
C52 C 0.465(2) 0.108(5) 0.4959(11) 0.098(11) Uani 0.50 1 d P
C53 C 0.634(3) 0.176(4) 0.5268(9) 0.145(6) Uani 1 1 d .
C54 C 0.478(6) 0.154(4) 0.4995(17) 0.19(3) Uani 0.47(4) 1 d P
C55 C 0.3530(17) -0.038(2) 0.4753(5) 0.121(7) Uani 0.90(4) 1 d P
C56 C 0.5709(15) 0.082(2) 0.5185(7) 0.027(7) Uani 0.29(4) 1 d P
C57 C 0.688(3) 0.234(3) 0.544(2) 0.24(3) Uani 0.38(3) 1 d P
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'
O O 0.0106 0.0060 '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'
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
C19 O20 C20 120.7(2) . .
C39 O40 C40 120.9(2) . .
C4 N1 C1 105.1(2) . .
C9 N2 C6 109.4(2) . .
C14 N5 C17 125.4(2) . .
C19 N6 C18 122.1(3) . .
C34 N7 C37 124.7(2) . .
C39 N8 C38 121.4(3) . .
N1 C1 C10 125.6(2) . 2_556
N1 C1 C2 110.7(2) . .
C10 C1 C2 123.7(2) 2_556 .
C3 C2 C1 106.9(2) . .
C2 C3 C4 106.8(2) . .
N1 C4 C5 125.7(2) . .
N1 C4 C3 110.5(2) . .
C5 C4 C3 123.8(2) . .
C6 C5 C4 125.4(2) . .
C6 C5 C11 117.0(2) . .
C4 C5 C11 117.5(2) . .
N2 C6 C5 125.7(2) . .
N2 C6 C7 107.2(2) . .
C5 C6 C7 127.0(2) . .
C8 C7 C6 107.8(2) . .
C7 C8 C9 108.3(2) . .
N2 C9 C10 125.9(2) . .
N2 C9 C8 107.2(2) . .
C10 C9 C8 126.8(2) . .
C9 C10 C1 126.2(2) . 2_556
C9 C10 C31 116.7(2) . .
C1 C10 C31 117.0(2) 2_556 .
C16 C11 C12 114.8(2) . .
C16 C11 C5 123.1(2) . .
C12 C11 C5 122.1(2) . .
F1 C12 C13 117.8(2) . .
F1 C12 C11 119.7(2) . .
C13 C12 C11 122.5(3) . .
F2 C13 C12 119.4(2) . .
F2 C13 C14 117.5(2) . .
C12 C13 C14 123.1(3) . .
N5 C14 C15 125.6(3) . .
N5 C14 C13 120.1(3) . .
C15 C14 C13 114.2(3) . .
F3 C15 C16 117.5(3) . .
F3 C15 C14 120.3(2) . .
C16 C15 C14 122.2(3) . .
F4 C16 C11 119.5(2) . .
F4 C16 C15 117.4(2) . .
C11 C16 C15 123.1(3) . .
N5 C17 C18 109.5(2) . .
N6 C18 C17 113.8(2) . .
O19 C19 N6 124.8(3) . .
O19 C19 O20 125.4(3) . .
N6 C19 O20 109.8(3) . .
O20 C20 C21 110.2(2) . .
O20 C20 C23 101.9(2) . .
C21 C20 C23 110.8(3) . .
O20 C20 C22 110.1(2) . .
C21 C20 C22 112.2(3) . .
C23 C20 C22 111.2(3) . .
C36 C31 C32 115.6(2) . .
C36 C31 C10 121.4(2) . .
C32 C31 C10 123.0(2) . .
F5 C32 C33 118.3(3) . .
F5 C32 C31 120.1(2) . .
C33 C32 C31 121.6(3) . .
F6 C33 C32 119.1(2) . .
F6 C33 C34 118.0(2) . .
C32 C33 C34 122.9(3) . .
N7 C34 C33 119.6(3) . .
N7 C34 C35 125.0(3) . .
C33 C34 C35 115.4(2) . .
F7 C35 C36 118.6(3) . .
F7 C35 C34 120.1(2) . .
C36 C35 C34 121.4(3) . .
F8 C36 C35 117.5(2) . .
F8 C36 C31 119.3(2) . .
C35 C36 C31 123.1(3) . .
N7 C37 C38 111.8(3) . .
N8 C38 C37 112.0(3) . .
O39 C39 O40 125.5(3) . .
O39 C39 N8 123.9(3) . .
O40 C39 N8 110.7(3) . .
O40 C40 C43 101.2(3) . .
O40 C40 C41 110.1(2) . .
C43 C40 C41 111.4(3) . .
O40 C40 C42 109.7(3) . .
C43 C40 C42 110.8(3) . .
C41 C40 C42 113.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C12 1.349(3) .
F2 C13 1.356(3) .
F3 C15 1.355(3) .
F4 C16 1.345(3) .
F5 C32 1.343(3) .
F6 C33 1.354(3) .
F7 C35 1.348(3) .
F8 C36 1.349(3) .
O19 C19 1.219(3) .
O20 C19 1.351(3) .
O20 C20 1.479(3) .
O39 C39 1.223(3) .
O40 C39 1.341(3) .
O40 C40 1.474(4) .
N1 C4 1.368(3) .
N1 C1 1.370(3) .
N2 C9 1.367(3) .
N2 C6 1.372(3) .
N5 C14 1.364(3) .
N5 C17 1.450(4) .
N6 C19 1.340(4) .
N6 C18 1.460(4) .
N7 C34 1.375(3) .
N7 C37 1.454(4) .
N8 C39 1.346(4) .
N8 C38 1.447(4) .
C1 C10 1.401(4) 2_556
C1 C2 1.440(4) .
C2 C3 1.338(4) .
C3 C4 1.446(4) .
C4 C5 1.401(4) .
C5 C6 1.400(4) .
C5 C11 1.493(4) .
C6 C7 1.427(4) .
C7 C8 1.351(4) .
C8 C9 1.424(4) .
C9 C10 1.397(4) .
C10 C1 1.401(4) 2_556
C10 C31 1.499(4) .
C11 C16 1.378(4) .
C11 C12 1.389(4) .
C12 C13 1.367(4) .
C13 C14 1.397(4) .
C14 C15 1.392(4) .
C15 C16 1.383(4) .
C17 C18 1.519(4) .
C20 C21 1.507(5) .
C20 C23 1.511(4) .
C20 C22 1.511(4) .
C31 C36 1.382(4) .
C31 C32 1.383(4) .
C32 C33 1.381(4) .
C33 C34 1.387(4) .
C34 C35 1.389(4) .
C35 C36 1.380(4) .
C37 C38 1.512(4) .
C40 C43 1.512(4) .
C40 C41 1.513(5) .
C40 C42 1.521(4) .
