#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:06:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178835 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/89/4108990.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_4108990
loop_
_publ_author_name
'Masaaki Suzuki'
'Atsuhiro Osuka'
_publ_section_title
;
 Cross-Bridging Reaction of 5,20-Diethynyl Substituted Hexaphyrins to
 Vinylene-Bridged Hexaphyrins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              464
_journal_page_last               465
_journal_paper_doi               10.1021/ja067102v
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C76 H56 F20 N6 Si2'
_chemical_formula_weight         1489.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                95.39(2)
_cell_angle_beta                 103.75(2)
_cell_angle_gamma                96.10(2)
_cell_formula_units_Z            1
_cell_length_a                   8.390(5)
_cell_length_b                   13.865(9)
_cell_length_c                   15.169(7)
_cell_measurement_temperature    293(2)
_cell_volume                     1691.3(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16131
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         7727
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       prism
_exptl_crystal_F_000             762
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         7507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0733
_refine_ls_shift/su_max          0.058
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1166P)²+0.6226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2220
_reflns_number_gt                4904
_reflns_number_total             7507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067102vsi20061213_025143.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1691.2(17)
_cod_database_code               4108990
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
Si1 Si 0.80197(11) -0.20561(6) 0.13470(6) 0.0304(2) Uani 1 1 d .
F1 F -0.1484(3) 0.17848(16) 0.16327(14) 0.0504(5) Uani 1 1 d .
F2 F -0.1996(3) 0.33905(19) 0.07951(14) 0.0640(7) Uani 1 1 d .
F3 F 0.0327(4) 0.49836(17) 0.12219(17) 0.0682(8) Uani 1 1 d .
F4 F 0.3203(3) 0.49639(16) 0.25134(19) 0.0638(7) Uani 1 1 d .
F5 F 0.3714(2) 0.33731(14) 0.33547(14) 0.0448(5) Uani 1 1 d .
F6 F 0.1865(3) -0.40265(14) 0.41567(13) 0.0450(5) Uani 1 1 d .
F7 F 0.1581(3) -0.58499(14) 0.46036(17) 0.0579(6) Uani 1 1 d .
F8 F 0.2022(3) -0.61570(14) 0.63908(18) 0.0627(7) Uani 1 1 d .
F9 F 0.2931(3) -0.46137(16) 0.77264(15) 0.0554(6) Uani 1 1 d .
F10 F 0.3386(2) -0.27972(13) 0.73056(12) 0.0396(4) Uani 1 1 d .
N1 N -0.0587(3) 0.21417(17) 0.37762(17) 0.0288(5) Uani 1 1 d .
N2 N 0.3171(3) 0.03148(17) 0.33271(17) 0.0288(5) Uani 1 1 d .
H7 H 0.2804 0.0090 0.3761 0.035 Uiso 1 1 calc R
N3 N 0.3821(3) -0.12699(17) 0.44329(16) 0.0287(5) Uani 1 1 d .
C1 C -0.1606(4) 0.1746(2) 0.42563(19) 0.0273(6) Uani 1 1 d .
C2 C -0.1378(4) 0.0719(2) 0.4344(2) 0.0284(6) Uani 1 1 d .
H1 H -0.1948 0.0286 0.4631 0.034 Uiso 1 1 calc R
C3 C -0.0182(4) 0.0530(2) 0.3924(2) 0.0291(6) Uani 1 1 d .
H2 H 0.0255 -0.0056 0.3872 0.035 Uiso 1 1 calc R
C4 C 0.0296(4) 0.1434(2) 0.35661(19) 0.0271(6) Uani 1 1 d .
C5 C 0.1389(4) 0.1625(2) 0.30118(19) 0.0278(6) Uani 1 1 d .
C6 C 0.2632(4) 0.1082(2) 0.2869(2) 0.0293(6) Uani 1 1 d .
C7 C 0.3589(4) 0.1230(2) 0.2214(2) 0.0353(7) Uani 1 1 d .
H3 H 0.3499 0.1705 0.1817 0.042 Uiso 1 1 calc R
C8 C 0.4651(4) 0.0552(2) 0.2275(2) 0.0346(7) Uani 1 1 d .
H4 H 0.5414 0.0475 0.1927 0.041 Uiso 1 1 calc R
C9 C 0.4380(4) -0.0022(2) 0.2975(2) 0.0290(6) Uani 1 1 d .
C10 C 0.5223(4) -0.0813(2) 0.3247(2) 0.0285(6) Uani 1 1 d .
C11 C 0.4985(4) -0.1370(2) 0.3947(2) 0.0293(6) Uani 1 1 d .
C12 C 0.5821(4) -0.2198(2) 0.4178(2) 0.0379(7) Uani 1 1 d .
H5 H 0.6697 -0.2398 0.3961 0.046 Uiso 1 1 calc R
C13 C 0.5091(4) -0.2627(2) 0.4768(2) 0.0372(7) Uani 1 1 d .
H6 H 0.5358 -0.3189 0.5028 0.045 Uiso 1 1 calc R
C14 C 0.3819(4) -0.2059(2) 0.4922(2) 0.0293(6) Uani 1 1 d .
C15 C 0.2712(4) -0.2312(2) 0.5456(2) 0.0289(6) Uani 1 1 d .
C16 C 0.1147(4) 0.2514(2) 0.2517(2) 0.0314(7) Uani 1 1 d .
C17 C -0.0304(4) 0.2557(2) 0.1867(2) 0.0371(7) Uani 1 1 d .
C18 C -0.0595(5) 0.3379(3) 0.1425(2) 0.0467(9) Uani 1 1 d .
C19 C 0.0582(5) 0.4189(3) 0.1643(3) 0.0474(9) Uani 1 1 d .
C20 C 0.2046(5) 0.4180(2) 0.2290(3) 0.0448(9) Uani 1 1 d .
C21 C 0.2299(4) 0.3344(2) 0.2714(2) 0.0339(7) Uani 1 1 d .
C22 C 0.6306(4) -0.1138(2) 0.2713(2) 0.0302(6) Uani 1 1 d .
C23 C 0.7111(4) -0.1474(2) 0.2223(2) 0.0332(7) Uani 1 1 d .
C24 C 0.7456(7) -0.1357(3) 0.0354(3) 0.0695(14) Uani 1 1 d .
H8 H 0.7893 -0.1648 -0.0139 0.083 Uiso 1 1 calc R
C25 C 0.5521(6) -0.1454(4) -0.0002(3) 0.0806(17) Uani 1 1 d .
H9 H 0.5072 -0.2133 -0.0139 0.097 Uiso 1 1 calc R
H10 H 0.5241 -0.1140 -0.0546 0.097 Uiso 1 1 calc R
H11 H 0.5066 -0.1148 0.0460 0.097 Uiso 1 1 calc R
C26 C 0.8167(10) -0.0311(3) 0.0566(5) 0.114(3) Uani 1 1 d .
H12 H 0.9350 -0.0259 0.0775 0.137 Uiso 1 1 calc R
H13 H 0.7730 -0.0004 0.1034 0.137 Uiso 1 1 calc R
H14 H 0.7881 0.0007 0.0025 0.137 Uiso 1 1 calc R
C27 C 1.0352(5) -0.1904(3) 0.1830(3) 0.0505(9) Uani 1 1 d .
H15 H 1.0692 -0.1211 0.2062 0.061 Uiso 1 1 calc R
C28 C 1.0821(5) -0.2459(4) 0.2636(3) 0.0623(12) Uani 1 1 d .
H16 H 1.0205 -0.2287 0.3072 0.075 Uiso 1 1 calc R
H17 H 1.1984 -0.2295 0.2915 0.075 Uiso 1 1 calc R
H18 H 1.0574 -0.3148 0.2435 0.075 Uiso 1 1 calc R
C29 C 1.1319(6) -0.2142(4) 0.1107(3) 0.0667(12) Uani 1 1 d .
H19 H 1.0994 -0.1771 0.0606 0.080 Uiso 1 1 calc R
H20 H 1.1080 -0.2827 0.0888 0.080 Uiso 1 1 calc R
H21 H 1.2485 -0.1976 0.1378 0.080 Uiso 1 1 calc R
C30 C 0.7138(5) -0.3388(2) 0.1109(3) 0.0458(8) Uani 1 1 d .
H22 H 0.7832 -0.3723 0.1565 0.055 Uiso 1 1 calc R
C31 C 0.7265(7) -0.3840(4) 0.0165(3) 0.0733(14) Uani 1 1 d .
H26 H 0.8383 -0.3702 0.0114 0.088 Uiso 1 1 calc R
H27 H 0.6536 -0.3566 -0.0306 0.088 Uiso 1 1 calc R
H28 H 0.6954 -0.4535 0.0098 0.088 Uiso 1 1 calc R
C32 C 0.5371(5) -0.3605(3) 0.1203(3) 0.0518(10) Uani 1 1 d .
H23 H 0.5056 -0.4300 0.1132 0.062 Uiso 1 1 calc R
H24 H 0.4635 -0.3325 0.0740 0.062 Uiso 1 1 calc R
H25 H 0.5309 -0.3327 0.1796 0.062 Uiso 1 1 calc R
C33 C 0.2623(4) -0.3337(2) 0.5712(2) 0.0310(6) Uani 1 1 d .
C34 C 0.2195(4) -0.4146(2) 0.5049(2) 0.0363(7) Uani 1 1 d .
C35 C 0.2006(5) -0.5093(2) 0.5269(3) 0.0434(8) Uani 1 1 d .
C36 C 0.2239(5) -0.5244(2) 0.6171(3) 0.0447(9) Uani 1 1 d .
C37 C 0.2673(4) -0.4465(2) 0.6838(2) 0.0403(8) Uani 1 1 d .
C38 C 0.2883(4) -0.3524(2) 0.6610(2) 0.0341(7) Uani 1 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 0.0033 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'
Si Si 0.0817 0.0704 '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
C23 Si1 C24 104.66(17) . .
C23 Si1 C30 107.86(16) . .
C24 Si1 C30 114.4(2) . .
C23 Si1 C27 107.68(17) . .
C24 Si1 C27 111.1(2) . .
C30 Si1 C27 110.77(18) . .
C4 N1 C1 106.4(2) . .
C9 N2 C6 108.3(2) . .
C9 N2 H7 125.9 . .
C6 N2 H7 125.9 . .
C11 N3 C14 106.1(2) . .
N1 C1 C15 119.0(2) . 2_556
N1 C1 C2 110.4(2) . .
C15 C1 C2 130.5(3) 2_556 .
C3 C2 C1 106.2(2) . .
C3 C2 H1 126.9 . .
C1 C2 H1 126.9 . .
C2 C3 C4 106.1(2) . .
C2 C3 H2 126.9 . .
C4 C3 H2 126.9 . .
N1 C4 C5 118.7(2) . .
N1 C4 C3 110.8(2) . .
C5 C4 C3 130.3(3) . .
C6 C5 C4 127.2(3) . .
C6 C5 C16 117.8(2) . .
C4 C5 C16 115.0(3) . .
N2 C6 C5 126.8(3) . .
N2 C6 C7 107.7(3) . .
C5 C6 C7 125.5(3) . .
C8 C7 C6 107.8(3) . .
C8 C7 H3 126.1 . .
C6 C7 H3 126.1 . .
C7 C8 C9 107.4(3) . .
C7 C8 H4 126.3 . .
C9 C8 H4 126.3 . .
N2 C9 C10 125.7(3) . .
N2 C9 C8 108.9(3) . .
C10 C9 C8 125.4(3) . .
C9 C10 C11 125.7(3) . .
C9 C10 C22 117.2(2) . .
C11 C10 C22 116.8(3) . .
N3 C11 C10 125.4(3) . .
N3 C11 C12 110.4(2) . .
C10 C11 C12 123.9(3) . .
C13 C12 C11 106.6(3) . .
C13 C12 H5 126.7 . .
C11 C12 H5 126.7 . .
C12 C13 C14 107.5(3) . .
C12 C13 H6 126.2 . .
C14 C13 H6 126.2 . .
N3 C14 C15 126.3(3) . .
N3 C14 C13 109.3(2) . .
C15 C14 C13 124.4(3) . .
C1 C15 C14 128.1(3) 2_556 .
C1 C15 C33 114.9(2) 2_556 .
C14 C15 C33 116.9(3) . .
C21 C16 C17 116.1(3) . .
C21 C16 C5 122.8(3) . .
C17 C16 C5 121.0(3) . .
F1 C17 C16 120.1(3) . .
F1 C17 C18 117.4(3) . .
C16 C17 C18 122.5(3) . .
F2 C18 C19 119.7(3) . .
F2 C18 C17 120.9(4) . .
C19 C18 C17 119.4(3) . .
F3 C19 C18 120.2(4) . .
F3 C19 C20 119.7(4) . .
C18 C19 C20 120.1(3) . .
F4 C20 C19 120.9(3) . .
F4 C20 C21 120.2(4) . .
C19 C20 C21 118.9(3) . .
F5 C21 C16 119.8(3) . .
F5 C21 C20 117.2(3) . .
C16 C21 C20 123.0(3) . .
C23 C22 C10 174.4(3) . .
C22 C23 Si1 170.9(3) . .
C26 C24 C25 110.1(4) . .
C26 C24 Si1 112.9(4) . .
C25 C24 Si1 110.0(3) . .
C26 C24 H8 107.9 . .
C25 C24 H8 107.9 . .
Si1 C24 H8 107.9 . .
C24 C25 H9 109.5 . .
C24 C25 H10 109.5 . .
H9 C25 H10 109.5 . .
C24 C25 H11 109.5 . .
H9 C25 H11 109.5 . .
H10 C25 H11 109.5 . .
C24 C26 H12 109.5 . .
C24 C26 H13 109.5 . .
H12 C26 H13 109.5 . .
C24 C26 H14 109.5 . .
H12 C26 H14 109.5 . .
H13 C26 H14 109.5 . .
C28 C27 C29 111.8(4) . .
C28 C27 Si1 111.6(3) . .
C29 C27 Si1 113.7(3) . .
C28 C27 H15 106.4 . .
C29 C27 H15 106.4 . .
Si1 C27 H15 106.4 . .
C27 C28 H16 109.5 . .
C27 C28 H17 109.5 . .
H16 C28 H17 109.5 . .
C27 C28 H18 109.5 . .
H16 C28 H18 109.5 . .
H17 C28 H18 109.5 . .
C27 C29 H19 109.5 . .
C27 C29 H20 109.5 . .
H19 C29 H20 109.5 . .
C27 C29 H21 109.5 . .
H19 C29 H21 109.5 . .
H20 C29 H21 109.5 . .
C32 C30 C31 110.1(3) . .
C32 C30 Si1 114.7(3) . .
C31 C30 Si1 111.4(3) . .
C32 C30 H22 106.7 . .
C31 C30 H22 106.7 . .
Si1 C30 H22 106.7 . .
C30 C31 H26 109.5 . .
C30 C31 H27 109.5 . .
H26 C31 H27 109.5 . .
C30 C31 H28 109.5 . .
H26 C31 H28 109.5 . .
H27 C31 H28 109.5 . .
C30 C32 H23 109.5 . .
C30 C32 H24 109.5 . .
H23 C32 H24 109.5 . .
C30 C32 H25 109.5 . .
H23 C32 H25 109.5 . .
H24 C32 H25 109.5 . .
C38 C33 C34 116.4(3) . .
C38 C33 C15 122.1(3) . .
C34 C33 C15 121.4(3) . .
F6 C34 C35 117.6(3) . .
F6 C34 C33 120.2(3) . .
C35 C34 C33 122.2(3) . .
F7 C35 C36 120.7(3) . .
F7 C35 C34 119.9(3) . .
C36 C35 C34 119.4(3) . .
F8 C36 C37 120.3(3) . .
F8 C36 C35 119.9(3) . .
C37 C36 C35 119.8(3) . .
F9 C37 C36 119.9(3) . .
F9 C37 C38 119.9(3) . .
C36 C37 C38 120.2(3) . .
F10 C38 C33 121.2(3) . .
F10 C38 C37 116.9(3) . .
C33 C38 C37 121.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C23 1.846(3) .
Si1 C24 1.862(4) .
Si1 C30 1.882(4) .
Si1 C27 1.900(4) .
F1 C17 1.337(4) .
F2 C18 1.329(4) .
F3 C19 1.337(4) .
F4 C20 1.337(4) .
F5 C21 1.338(4) .
F6 C34 1.345(4) .
F7 C35 1.341(4) .
F8 C36 1.344(3) .
F9 C37 1.352(4) .
F10 C38 1.344(4) .
N1 C4 1.349(4) .
N1 C1 1.354(4) .
N2 C9 1.358(4) .
N2 C6 1.383(4) .
N2 H7 0.8600 .
N3 C11 1.366(4) .
N3 C14 1.378(4) .
C1 C15 1.397(4) 2_556
C1 C2 1.471(4) .
C2 C3 1.345(4) .
C2 H1 0.9300 .
C3 C4 1.468(4) .
C3 H2 0.9300 .
C4 C5 1.405(4) .
C5 C6 1.395(4) .
C5 C16 1.509(4) .
C6 C7 1.434(4) .
C7 C8 1.357(4) .
C7 H3 0.9300 .
C8 C9 1.430(4) .
C8 H4 0.9300 .
C9 C10 1.408(4) .
C10 C11 1.409(4) .
C10 C22 1.434(4) .
C11 C12 1.436(4) .
C12 C13 1.347(4) .
C12 H5 0.9300 .
C13 C14 1.441(4) .
C13 H6 0.9300 .
C14 C15 1.409(4) .
C15 C1 1.397(4) 2_556
C15 C33 1.508(4) .
C16 C21 1.382(5) .
C16 C17 1.384(5) .
C17 C18 1.390(5) .
C18 C19 1.372(6) .
C19 C20 1.379(6) .
C20 C21 1.389(4) .
C22 C23 1.210(4) .
C24 C26 1.483(7) .
C24 C25 1.571(7) .
C24 H8 0.9800 .
C25 H9 0.9600 .
C25 H10 0.9600 .
C25 H11 0.9600 .
C26 H12 0.9600 .
C26 H13 0.9600 .
C26 H14 0.9600 .
C27 C28 1.500(6) .
C27 C29 1.543(5) .
C27 H15 0.9800 .
C28 H16 0.9600 .
C28 H17 0.9600 .
C28 H18 0.9600 .
C29 H19 0.9600 .
C29 H20 0.9600 .
C29 H21 0.9600 .
C30 C32 1.524(5) .
C30 C31 1.541(6) .
C30 H22 0.9800 .
C31 H26 0.9600 .
C31 H27 0.9600 .
C31 H28 0.9600 .
C32 H23 0.9600 .
C32 H24 0.9600 .
C32 H25 0.9600 .
C33 C38 1.382(4) .
C33 C34 1.389(5) .
C34 C35 1.387(4) .
C35 C36 1.375(5) .
C36 C37 1.363(5) .
C37 C38 1.385(4) .
