#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:57:02 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178830 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/84/4108446.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_4108446
loop_
_publ_author_name
'Jeyaraman Sankar'
'Shigeki Mori'
'Shohei Saito'
'Harapriya Rath'
'Masaaki Suzuki'
'Yasuhide Inokuma'
'Hiroshi Shinokubo'
'Kil Suk Kim'
'Zin Seok Yoon'
'Jae-Yoon Shin'
'Jong Min Lim'
'Yoichi Matsuzaki'
'Osamu Matsushita'
'Atsuya Muranaka'
'Nagao Kobayashi'
'Dongho Kim'
'Atsuhiro Osuka'
_publ_section_title
;
 Unambiguous Identification of Möbius Aromaticity for
 meso-Aryl-Substituted [28]Hexaphyrins(1.1.1.1.1.1)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13568
_journal_page_last               13579
_journal_paper_doi               10.1021/ja801983d
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C66 H16 F30 N6, 2(C2 H6 O S)'
_chemical_formula_sum            'C70 H28 F30 N6 O2 S2'
_chemical_formula_weight         1619.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.097(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.7892(19)
_cell_length_b                   12.9847(17)
_cell_length_c                   18.106(3)
_cell_measurement_reflns_used    7595
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.17
_cell_volume                     3201.1(8)
_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      90(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19367
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9457
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_description       prism
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         7294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0501
_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)+(0.0643P)²+1.4397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                4849
_reflns_number_total             7294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja801983d_si_004.cif
_cod_data_source_block           71104moris
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4108446
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.26507(17) 0.86058(18) 0.19189(13) 0.0185(5) Uani 1 1 d .
C2 C 0.17004(17) 0.90009(19) 0.20204(13) 0.0204(5) Uani 1 1 d .
H2 H 0.1295 0.8730 0.2352 0.024 Uiso 1 1 calc R
C3 C 0.14893(17) 0.98129(19) 0.15689(13) 0.0214(5) Uani 1 1 d .
H3 H 0.0912 1.0221 0.1532 0.026 Uiso 1 1 calc R
C4 C 0.22817(16) 0.99691(18) 0.11456(13) 0.0183(5) Uani 1 1 d .
C5 C 0.76748(17) 0.92767(18) -0.06224(13) 0.0189(5) Uani 1 1 d .
C6 C 0.69647(16) 0.91945(18) -0.01191(12) 0.0174(5) Uani 1 1 d .
C7 C 0.63228(17) 0.98906(18) 0.01343(13) 0.0189(5) Uani 1 1 d .
H7 H 0.6196 1.0574 -0.0041 0.023 Uiso 1 1 calc R
C8 C 0.58975(17) 0.94027(18) 0.06944(13) 0.0193(5) Uani 1 1 d .
H8 H 0.5429 0.9695 0.0965 0.023 Uiso 1 1 calc R
C9 C 0.62832(16) 0.84148(18) 0.07823(13) 0.0177(5) Uani 1 1 d .
C10 C 0.62453(16) 0.76149(18) 0.13272(13) 0.0179(5) Uani 1 1 d .
C11 C 0.55187(17) 0.74259(18) 0.17472(13) 0.0189(5) Uani 1 1 d .
C12 C 0.55630(18) 0.66489(18) 0.23250(13) 0.0207(5) Uani 1 1 d .
H12 H 0.6091 0.6188 0.2481 0.025 Uiso 1 1 calc R
C13 C 0.47145(18) 0.67045(19) 0.25983(13) 0.0215(5) Uani 1 1 d .
H13 H 0.4526 0.6293 0.2985 0.026 Uiso 1 1 calc R
C14 C 0.41400(17) 0.75197(18) 0.21852(13) 0.0183(5) Uani 1 1 d .
C15 C 0.31840(17) 0.78230(18) 0.23037(13) 0.0189(5) Uani 1 1 d .
C16 C 0.84393(17) 0.84555(19) -0.05560(13) 0.0202(5) Uani 1 1 d .
C17 C 0.91430(18) 0.83275(19) 0.00749(14) 0.0243(5) Uani 1 1 d .
C18 C 0.98061(18) 0.7529(2) 0.01519(15) 0.0284(6) Uani 1 1 d .
C19 C 0.9773(2) 0.6813(2) -0.04098(15) 0.0364(7) Uani 1 1 d .
C20 C 0.9087(3) 0.6909(3) -0.10373(16) 0.0500(9) Uani 1 1 d .
C21 C 0.8439(2) 0.7720(2) -0.11021(15) 0.0369(7) Uani 1 1 d .
C22 C 0.71497(16) 0.69672(18) 0.14624(12) 0.0181(5) Uani 1 1 d .
C23 C 0.80490(17) 0.74121(18) 0.17423(13) 0.0206(5) Uani 1 1 d .
C24 C 0.89080(18) 0.6860(2) 0.18462(14) 0.0252(6) Uani 1 1 d .
C25 C 0.88916(17) 0.5835(2) 0.16423(14) 0.0245(6) Uani 1 1 d .
C26 C 0.80125(18) 0.53758(19) 0.13604(14) 0.0232(5) Uani 1 1 d .
C27 C 0.71591(17) 0.59292(19) 0.12843(13) 0.0205(5) Uani 1 1 d .
C28 C 0.27425(17) 0.72980(18) 0.29039(13) 0.0202(5) Uani 1 1 d .
C29 C 0.30505(18) 0.75203(19) 0.36481(14) 0.0242(5) Uani 1 1 d .
C30 C 0.2598(2) 0.7116(2) 0.42122(14) 0.0274(6) Uani 1 1 d .
C31 C 0.18186(19) 0.6458(2) 0.40311(15) 0.0271(6) Uani 1 1 d .
C32 C 0.15109(18) 0.6183(2) 0.32999(15) 0.0260(6) Uani 1 1 d .
C33 C 0.19721(17) 0.6599(2) 0.27484(14) 0.0230(5) Uani 1 1 d .
F1 F 0.16611(11) 0.63171(12) 0.20388(8) 0.0313(4) Uani 1 1 d .
F2 F 0.07667(11) 0.55209(13) 0.31354(9) 0.0399(4) Uani 1 1 d .
F3 F 0.13591(12) 0.60855(12) 0.45753(9) 0.0388(4) Uani 1 1 d .
F4 F 0.29081(14) 0.73697(12) 0.49275(8) 0.0416(4) Uani 1 1 d .
F5 F 0.38051(11) 0.81724(12) 0.38418(8) 0.0322(4) Uani 1 1 d .
F6 F 0.63180(10) 0.54523(11) 0.10033(8) 0.0282(3) Uani 1 1 d .
F7 F 0.80067(11) 0.43794(11) 0.11576(9) 0.0312(4) Uani 1 1 d .
F8 F 0.97196(11) 0.52848(12) 0.17289(9) 0.0365(4) Uani 1 1 d .
F9 F 0.97503(10) 0.73037(12) 0.21623(10) 0.0387(4) Uani 1 1 d .
F10 F 0.80804(10) 0.84103(11) 0.19338(8) 0.0282(3) Uani 1 1 d .
F11 F 0.77493(15) 0.77640(15) -0.17182(9) 0.0598(6) Uani 1 1 d .
F12 F 0.9015(2) 0.6192(2) -0.15738(12) 0.1046(12) Uani 1 1 d .
F13 F 1.04061(14) 0.60270(15) -0.03278(10) 0.0568(6) Uani 1 1 d .
F14 F 1.04849(12) 0.74422(14) 0.07612(10) 0.0460(5) Uani 1 1 d .
F15 F 0.91856(13) 0.90024(13) 0.06402(10) 0.0444(5) Uani 1 1 d .
N1 N 0.29612(14) 0.92032(15) 0.13745(10) 0.0181(4) Uani 1 1 d .
H1N H 0.3513 0.9112 0.1197 0.022 Uiso 1 1 calc R
N2 N 0.69268(14) 0.83054(15) 0.02808(10) 0.0176(4) Uani 1 1 d .
H2N H 0.7266 0.7744 0.0225 0.021 Uiso 1 1 calc R
N3 N 0.46253(14) 0.79521(15) 0.16803(10) 0.0177(4) Uani 1 1 d .
O1S O 0.28670(15) 0.36720(14) 0.03658(10) 0.0343(5) Uani 1 1 d .
S1S S 0.37990(7) 0.42117(6) 0.07283(5) 0.0492(2) Uani 1 1 d .
C1S C 0.3547(3) 0.5548(2) 0.06467(19) 0.0561(10) Uani 1 1 d .
H1S1 H 0.3509 0.5758 0.0123 0.084 Uiso 1 1 calc R
H1S2 H 0.4074 0.5932 0.0956 0.084 Uiso 1 1 calc R
H1S3 H 0.2921 0.5694 0.0816 0.084 Uiso 1 1 calc R
C2S C 0.3824(4) 0.4123(3) 0.1706(2) 0.0927(18) Uani 1 1 d .
H2S1 H 0.3193 0.4355 0.1831 0.139 Uiso 1 1 calc R
H2S2 H 0.4353 0.4559 0.1963 0.139 Uiso 1 1 calc R
H2S3 H 0.3941 0.3407 0.1866 0.139 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 C1 C15 125.3(2) .
N1 C1 C2 106.4(2) .
C15 C1 C2 128.3(2) .
C3 C2 C1 108.4(2) .
C3 C2 H2 125.8 .
C1 C2 H2 125.8 .
C2 C3 C4 109.0(2) .
C2 C3 H3 125.5 .
C4 C3 H3 125.5 .
C5 C4 N1 128.2(2) 3_675
C5 C4 C3 125.9(2) 3_675
N1 C4 C3 105.85(19) .
C4 C5 C6 126.7(2) 3_675
C4 C5 C16 117.3(2) 3_675
C6 C5 C16 116.0(2) .
N2 C6 C7 107.1(2) .
N2 C6 C5 118.9(2) .
C7 C6 C5 133.6(2) .
C6 C7 C8 107.8(2) .
C6 C7 H7 126.1 .
C8 C7 H7 126.1 .
C9 C8 C7 107.7(2) .
C9 C8 H8 126.1 .
C7 C8 H8 126.1 .
N2 C9 C8 107.2(2) .
N2 C9 C10 118.4(2) .
C8 C9 C10 133.7(2) .
C11 C10 C9 128.2(2) .
C11 C10 C22 118.2(2) .
C9 C10 C22 113.54(19) .
C10 C11 N3 125.1(2) .
C10 C11 C12 125.0(2) .
N3 C11 C12 109.8(2) .
C13 C12 C11 106.8(2) .
C13 C12 H12 126.6 .
C11 C12 H12 126.6 .
C12 C13 C14 106.5(2) .
C12 C13 H13 126.7 .
C14 C13 H13 126.7 .
N3 C14 C15 124.2(2) .
N3 C14 C13 111.4(2) .
C15 C14 C13 124.4(2) .
C1 C15 C14 124.1(2) .
C1 C15 C28 117.3(2) .
C14 C15 C28 118.5(2) .
C21 C16 C17 115.5(2) .
C21 C16 C5 121.3(2) .
C17 C16 C5 123.1(2) .
F15 C17 C18 117.8(2) .
F15 C17 C16 119.4(2) .
C18 C17 C16 122.8(2) .
F14 C18 C19 119.5(2) .
F14 C18 C17 121.1(2) .
C19 C18 C17 119.5(2) .
F13 C19 C20 121.2(3) .
F13 C19 C18 119.3(2) .
C20 C19 C18 119.5(2) .
F12 C20 C19 120.2(3) .
F12 C20 C21 119.9(3) .
C19 C20 C21 119.8(3) .
F11 C21 C20 117.9(2) .
F11 C21 C16 119.1(2) .
C20 C21 C16 123.0(3) .
C27 C22 C23 116.6(2) .
C27 C22 C10 123.2(2) .
C23 C22 C10 120.0(2) .
F10 C23 C24 118.5(2) .
F10 C23 C22 119.1(2) .
C24 C23 C22 122.3(2) .
F9 C24 C23 120.3(2) .
F9 C24 C25 120.3(2) .
C23 C24 C25 119.3(2) .
F8 C25 C26 119.9(2) .
F8 C25 C24 120.5(2) .
C26 C25 C24 119.6(2) .
F7 C26 C27 120.7(2) .
F7 C26 C25 119.1(2) .
C27 C26 C25 120.2(2) .
F6 C27 C26 118.3(2) .
F6 C27 C22 119.8(2) .
C26 C27 C22 121.8(2) .
C29 C28 C33 116.2(2) .
C29 C28 C15 121.2(2) .
C33 C28 C15 122.5(2) .
F5 C29 C28 119.6(2) .
F5 C29 C30 117.9(2) .
C28 C29 C30 122.5(2) .
F4 C30 C31 120.2(2) .
F4 C30 C29 120.6(2) .
C31 C30 C29 119.2(2) .
F3 C31 C30 119.5(2) .
F3 C31 C32 120.3(2) .
C30 C31 C32 120.3(2) .
F2 C32 C31 119.5(2) .
F2 C32 C33 121.2(2) .
C31 C32 C33 119.3(2) .
F1 C33 C32 118.3(2) .
F1 C33 C28 119.4(2) .
C32 C33 C28 122.3(2) .
C1 N1 C4 110.32(19) .
C1 N1 H1N 124.8 .
C4 N1 H1N 124.8 .
C6 N2 C9 110.20(19) .
C6 N2 H2N 124.9 .
C9 N2 H2N 124.9 .
C14 N3 C11 105.36(19) .
O1S S1S C2S 106.50(19) .
O1S S1S C1S 105.95(15) .
C2S S1S C1S 96.87(18) .
S1S C1S H1S1 109.5 .
S1S C1S H1S2 109.5 .
H1S1 C1S H1S2 109.5 .
S1S C1S H1S3 109.5 .
H1S1 C1S H1S3 109.5 .
H1S2 C1S H1S3 109.5 .
S1S C2S H2S1 109.5 .
S1S C2S H2S2 109.5 .
H2S1 C2S H2S2 109.5 .
S1S C2S H2S3 109.5 .
H2S1 C2S H2S3 109.5 .
H2S2 C2S H2S3 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.375(3) .
C1 C15 1.377(3) .
C1 C2 1.446(3) .
C2 C3 1.338(3) .
C2 H2 0.9500 .
C3 C4 1.445(3) .
C3 H3 0.9500 .
C4 C5 1.370(3) 3_675
C4 N1 1.384(3) .
C5 C4 1.370(3) 3_675
C5 C6 1.443(3) .
C5 C16 1.491(3) .
C6 N2 1.368(3) .
C6 C7 1.393(3) .
C7 C8 1.401(3) .
C7 H7 0.9500 .
C8 C9 1.388(3) .
C8 H8 0.9500 .
C9 N2 1.374(3) .
C9 C10 1.439(3) .
C10 C11 1.372(3) .
C10 C22 1.492(3) .
C11 N3 1.397(3) .
C11 C12 1.448(3) .
C12 C13 1.342(3) .
C12 H12 0.9500 .
C13 C14 1.456(3) .
C13 H13 0.9500 .
C14 N3 1.339(3) .
C14 C15 1.424(3) .
C15 C28 1.492(3) .
C16 C21 1.375(4) .
C16 C17 1.387(3) .
C17 F15 1.342(3) .
C17 C18 1.375(4) .
C18 F14 1.334(3) .
C18 C19 1.374(4) .
C19 F13 1.336(3) .
C19 C20 1.364(4) .
C20 F12 1.337(4) .
C20 C21 1.374(4) .
C21 F11 1.348(3) .
C22 C27 1.386(3) .
C22 C23 1.389(3) .
C23 F10 1.341(3) .
C23 C24 1.372(3) .
C24 F9 1.341(3) .
C24 C25 1.381(4) .
C25 F8 1.335(3) .
C25 C26 1.375(4) .
C26 F7 1.345(3) .
C26 C27 1.367(3) .
C27 F6 1.342(3) .
C28 C29 1.378(3) .
C28 C33 1.392(3) .
C29 F5 1.344(3) .
C29 C30 1.382(3) .
C30 F4 1.339(3) .
C30 C31 1.371(4) .
C31 F3 1.343(3) .
C31 C32 1.372(4) .
C32 F2 1.336(3) .
C32 C33 1.376(3) .
C33 F1 1.339(3) .
N1 H1N 0.8800 .
N2 H2N 0.8800 .
O1S S1S 1.519(2) .
S1S C2S 1.769(4) .
S1S C1S 1.771(3) .
C1S H1S1 0.9800 .
C1S H1S2 0.9800 .
C1S H1S3 0.9800 .
C2S H2S1 0.9800 .
C2S H2S2 0.9800 .
C2S H2S3 0.9800 .
