#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:05:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178933 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/62/4116268.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_4116268
loop_
_publ_author_name
'Jun-ichiro Setsune'
'Satoshi Maeda'
_publ_section_title
;
 Bis(azafulvene) as a Versatile Building Block for Giant
 Cyclopolypyrroles: X-ray Crystal Structure of
 [64]Hexadecaphyrin(1.0.1.0.1.0.1.0.1.0.1.0.1.0.1.0)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12405
_journal_page_last               12406
_journal_paper_doi               10.1021/ja005588o
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C184 H208 N16'
_chemical_formula_weight         2643.66
_chemical_name_systematic
; 
2,3,7,8,11,12,16,17,20,21,25,26,29,30,34,35,38,39,43,44,47,48,52,53,56,57,
61,62,65,66,70,71-dotriacontaethyl-5,14,23,32,41,50,59,68-
octaphenyl-[64]hexadecaphyrin-(1.0.1.0.1.0.1.0.1.0.1.0.1.0.1.0)  
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.085(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   34.611(3)
_cell_length_b                   14.3764(14)
_cell_length_c                   34.408(4)
_cell_measurement_temperature    293(2)
_cell_volume                     17077(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.877
_diffrn_measured_fraction_theta_max 0.877
_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  0.1135
_diffrn_reflns_av_sigmaI/netI    0.1372
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            45557
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             5696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     928
_refine_ls_number_reflns         17212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.2453
_refine_ls_R_factor_gt           0.0968
_refine_ls_shift/su_max          1.296
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1647P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2442
_refine_ls_wR_factor_ref         0.3280
_reflns_number_gt                5816
_reflns_number_total             17212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja005588o_s2.cif
_cod_data_source_block           p16p
_cod_database_code               4116268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.00267(14) 0.7687(3) 0.10089(17) 0.0706(15) Uani 1 1 d . . .
C2 C -0.02107(15) 0.6823(3) 0.10373(18) 0.0774(16) Uani 1 1 d . . .
C3 C 0.00368(15) 0.6149(3) 0.09105(16) 0.0726(14) Uani 1 1 d . . .
C4 C 0.03785(14) 0.6624(3) 0.07975(15) 0.0617(13) Uani 1 1 d . . .
C5 C 0.07118(14) 0.6328(3) 0.06249(13) 0.0571(12) Uani 1 1 d . . .
C6 C 0.10275(13) 0.6902(3) 0.05621(13) 0.0532(11) Uani 1 1 d . . .
C7 C 0.13689(14) 0.6776(3) 0.03538(13) 0.0604(13) Uani 1 1 d . . .
C8 C 0.15741(14) 0.7598(3) 0.03845(14) 0.0634(13) Uani 1 1 d . . .
C9 C 0.13624(14) 0.8205(3) 0.06177(13) 0.0557(12) Uani 1 1 d . . .
C10 C 0.14661(12) 0.9133(3) 0.07644(13) 0.0532(11) Uani 1 1 d . . .
C11 C 0.15402(15) 0.9965(3) 0.05768(14) 0.0669(13) Uani 1 1 d . . .
C12 C 0.15997(14) 1.0652(3) 0.08672(14) 0.0632(13) Uani 1 1 d . . .
C13 C 0.15582(12) 1.0232(3) 0.12296(13) 0.0505(11) Uani 1 1 d . . .
C14 C 0.15531(13) 1.0593(3) 0.16124(13) 0.0544(12) Uani 1 1 d . . .
C15 C 0.15522(13) 1.0044(3) 0.19446(13) 0.0559(12) Uani 1 1 d . . .
C16 C 0.14553(14) 1.0279(3) 0.23383(13) 0.0589(12) Uani 1 1 d . . .
C17 C 0.14867(14) 0.9478(3) 0.25487(13) 0.0587(12) Uani 1 1 d . . .
C18 C 0.16200(14) 0.8768(3) 0.22852(13) 0.0569(12) Uani 1 1 d . . .
C19 C 0.17357(14) 0.7820(3) 0.23803(13) 0.0571(12) Uani 1 1 d . . .
C20 C 0.18549(14) 0.7075(3) 0.21359(13) 0.0604(12) Uani 1 1 d . . .
C21 C 0.19474(13) 0.6321(3) 0.23801(13) 0.0581(12) Uani 1 1 d . . .
C22 C 0.18779(13) 0.6597(3) 0.27688(13) 0.0547(12) Uani 1 1 d . . .
C23 C 0.18928(13) 0.6096(3) 0.31229(13) 0.0541(11) Uani 1 1 d . . .
C24 C 0.18493(13) 0.6501(3) 0.34868(13) 0.0533(11) Uani 1 1 d . . .
C25 C 0.1793(2) 0.6118(3) 0.38603(16) 0.100(2) Uani 1 1 d . . .
C26 C 0.1716(2) 0.6844(4) 0.40960(17) 0.103(2) Uani 1 1 d . . .
C27 C 0.17327(12) 0.7666(3) 0.38727(13) 0.0523(11) Uani 1 1 d . . .
C28 C 0.16452(13) 0.8629(3) 0.39766(12) 0.0476(11) Uani 1 1 d . . .
C29 C 0.18871(13) 0.9395(3) 0.40487(14) 0.0615(13) Uani 1 1 d . . .
C30 C 0.16511(13) 1.0174(3) 0.40765(14) 0.0563(12) Uani 1 1 d . . .
C31 C 0.12609(13) 0.9859(3) 0.40160(12) 0.0491(11) Uani 1 1 d . . .
C32 C 0.08980(14) 1.0312(3) 0.39911(14) 0.0564(12) Uani 1 1 d . . .
C33 C 0.05443(14) 0.9851(3) 0.39392(16) 0.0665(14) Uani 1 1 d . . .
C34 C 0.01601(15) 1.0195(3) 0.38406(19) 0.0832(17) Uani 1 1 d . A .
C35 C -0.00845(15) 0.9436(4) 0.38191(19) 0.0871(18) Uani 1 1 d . . .
C36 C 0.01567(15) 0.8640(3) 0.39216(17) 0.0738(15) Uani 1 1 d . . .
C37 C -0.06072(19) 0.6666(4) 0.1174(3) 0.117(3) Uani 1 1 d . . .
H37A H -0.0776 0.7162 0.1073 0.141 Uiso 1 1 calc R . .
H37B H -0.0708 0.6086 0.1064 0.141 Uiso 1 1 calc R . .
C38 C -0.0623(3) 0.6630(9) 0.1576(4) 0.215(5) Uani 1 1 d . . .
H38A H -0.0549 0.6021 0.1668 0.323 Uiso 1 1 calc R . .
H38B H -0.0881 0.6763 0.1643 0.323 Uiso 1 1 calc R . .
H38C H -0.0448 0.7083 0.1696 0.323 Uiso 1 1 calc R . .
C39 C -0.00394(18) 0.5134(3) 0.0932(2) 0.098(2) Uani 1 1 d . . .
H39A H 0.0074 0.4828 0.0715 0.118 Uiso 1 1 calc R . .
H39B H -0.0317 0.5029 0.0904 0.118 Uiso 1 1 calc R . .
C40 C 0.0121(3) 0.4701(5) 0.1305(3) 0.157(3) Uani 1 1 d . . .
H40A H 0.0396 0.4804 0.1336 0.235 Uiso 1 1 calc R . .
H40B H 0.0070 0.4044 0.1299 0.235 Uiso 1 1 calc R . .
H40C H 0.0000 0.4976 0.1520 0.235 Uiso 1 1 calc R . .
C41 C 0.07282(14) 0.5339(3) 0.04925(15) 0.0623(13) Uani 1 1 d . . .
C42 C 0.09445(18) 0.4689(4) 0.07094(17) 0.0922(18) Uani 1 1 d . . .
H42 H 0.1082 0.4867 0.0940 0.111 Uiso 1 1 calc R . .
C43 C 0.0958(2) 0.3766(4) 0.0584(2) 0.125(3) Uani 1 1 d . . .
H43 H 0.1102 0.3327 0.0731 0.150 Uiso 1 1 calc R . .
C44 C 0.0754(2) 0.3514(4) 0.0240(3) 0.116(2) Uani 1 1 d . . .
H44 H 0.0763 0.2902 0.0154 0.139 Uiso 1 1 calc R . .
C45 C 0.05426(18) 0.4140(4) 0.00305(19) 0.0965(19) Uani 1 1 d . . .
H45 H 0.0403 0.3956 -0.0198 0.116 Uiso 1 1 calc R . .
C46 C 0.05294(15) 0.5062(3) 0.01496(17) 0.0775(15) Uani 1 1 d . . .
H46 H 0.0386 0.5494 -0.0002 0.093 Uiso 1 1 calc R . .
C47 C 0.14998(16) 0.5946(4) 0.01286(17) 0.0819(16) Uani 1 1 d . . .
H47A H 0.1278 0.5548 0.0064 0.098 Uiso 1 1 calc R . .
H47B H 0.1596 0.6161 -0.0114 0.098 Uiso 1 1 calc R . .
C48 C 0.1809(2) 0.5388(5) 0.0347(3) 0.138(3) Uani 1 1 d . . .
H48A H 0.2035 0.5766 0.0398 0.207 Uiso 1 1 calc R . .
H48B H 0.1872 0.4858 0.0194 0.207 Uiso 1 1 calc R . .
H48C H 0.1717 0.5181 0.0589 0.207 Uiso 1 1 calc R . .
C49 C 0.19675(18) 0.7801(4) 0.02480(19) 0.0956(19) Uani 1 1 d . . .
H49A H 0.1962 0.8403 0.0120 0.115 Uiso 1 1 calc R . .
H49B H 0.2029 0.7337 0.0057 0.115 Uiso 1 1 calc R . .
C50 C 0.2283(2) 0.7804(6) 0.0577(3) 0.143(3) Uani 1 1 d . . .
H50A H 0.2219 0.8246 0.0772 0.215 Uiso 1 1 calc R . .
H50B H 0.2525 0.7974 0.0477 0.215 Uiso 1 1 calc R . .
H50C H 0.2305 0.7195 0.0691 0.215 Uiso 1 1 calc R . .
C51 C 0.1495(2) 1.0111(4) 0.01471(16) 0.103(2) Uani 1 1 d . . .
H51A H 0.1513 0.9519 0.0015 0.124 Uiso 1 1 calc R . .
H51B H 0.1702 1.0508 0.0067 0.124 Uiso 1 1 calc R . .
C52 C 0.1085(3) 1.0583(6) 0.0030(3) 0.186(4) Uani 1 1 d . . .
H52A H 0.0881 1.0159 0.0083 0.280 Uiso 1 1 calc R . .
H52B H 0.1067 1.0733 -0.0243 0.280 Uiso 1 1 calc R . .
H52C H 0.1059 1.1141 0.0179 0.280 Uiso 1 1 calc R . .
C53 C 0.1725(2) 1.1628(3) 0.07831(17) 0.0903(18) Uani 1 1 d . . .
H53A H 0.1624 1.1799 0.0523 0.108 Uiso 1 1 calc R . .
H53B H 0.1614 1.2049 0.0965 0.108 Uiso 1 1 calc R . .
C54 C 0.2143(3) 1.1744(5) 0.0811(3) 0.168(4) Uani 1 1 d . . .
H54A H 0.2248 1.1513 0.1058 0.253 Uiso 1 1 calc R . .
H54B H 0.2205 1.2392 0.0789 0.253 Uiso 1 1 calc R . .
H54C H 0.2251 1.1404 0.0605 0.253 Uiso 1 1 calc R . .
C55 C 0.15294(16) 1.1620(3) 0.16576(14) 0.0636(13) Uani 1 1 d . . .
C56 C 0.11929(18) 1.2085(4) 0.15547(16) 0.0844(17) Uani 1 1 d . . .
H56 H 0.0980 1.1759 0.1445 0.101 Uiso 1 1 calc R . .
C57 C 0.1166(2) 1.3045(4) 0.1613(2) 0.108(2) Uani 1 1 d . . .
H57 H 0.0932 1.3353 0.1554 0.130 Uiso 1 1 calc R . .
C58 C 0.1478(3) 1.3515(5) 0.1754(2) 0.116(3) Uani 1 1 d . . .
H58 H 0.1463 1.4157 0.1783 0.140 Uiso 1 1 calc R . .
C59 C 0.1812(3) 1.3080(4) 0.1854(2) 0.109(2) Uani 1 1 d . . .
H59 H 0.2025 1.3417 0.1956 0.131 Uiso 1 1 calc R . .
C60 C 0.18414(18) 1.2120(3) 0.18047(16) 0.0830(16) Uani 1 1 d . . .
H60 H 0.2074 1.1819 0.1873 0.100 Uiso 1 1 calc R . .
C61 C 0.13050(18) 1.1178(3) 0.24897(15) 0.0798(16) Uani 1 1 d . . .
H61A H 0.1417 1.1689 0.2352 0.096 Uiso 1 1 calc R . .
H61B H 0.1390 1.1236 0.2763 0.096 Uiso 1 1 calc R . .
C62 C 0.0870(2) 1.1262(5) 0.2446(2) 0.138(3) Uani 1 1 d . . .
H62A H 0.0783 1.1205 0.2176 0.207 Uiso 1 1 calc R . .
H62B H 0.0795 1.1858 0.2542 0.207 Uiso 1 1 calc R . .
H62C H 0.0757 1.0779 0.2593 0.207 Uiso 1 1 calc R . .
C63 C 0.13647(17) 0.9347(3) 0.29544(14) 0.0749(15) Uani 1 1 d . . .
H63A H 0.1329 0.9952 0.3071 0.090 Uiso 1 1 calc R . .
H63B H 0.1570 0.9030 0.3109 0.090 Uiso 1 1 calc R . .
C64 C 0.09955(19) 0.8796(5) 0.29660(18) 0.111(2) Uani 1 1 d . . .
H64A H 0.0791 0.9107 0.2814 0.166 Uiso 1 1 calc R . .
H64B H 0.0927 0.8743 0.3231 0.166 Uiso 1 1 calc R . .
H64C H 0.1033 0.8186 0.2861 0.166 Uiso 1 1 calc R . .
C65 C 0.18501(18) 0.7061(3) 0.17020(15) 0.0849(17) Uani 1 1 d . . .
H65A H 0.1891 0.7689 0.1610 0.102 Uiso 1 1 calc R . .
H65B H 0.2064 0.6682 0.1626 0.102 Uiso 1 1 calc R . .
C66 C 0.1487(2) 0.6698(5) 0.1509(2) 0.137(3) Uani 1 1 d . . .
H66A H 0.1271 0.7031 0.1601 0.206 Uiso 1 1 calc R . .
H66B H 0.1463 0.6049 0.1567 0.206 Uiso 1 1 calc R . .
H66C H 0.1491 0.6779 0.1232 0.206 Uiso 1 1 calc R . .
C67 C 0.21201(15) 0.5437(3) 0.22403(14) 0.0665(14) Uani 1 1 d . . .
H67A H 0.2033 0.5341 0.1969 0.080 Uiso 1 1 calc R . .
H67B H 0.2028 0.4920 0.2389 0.080 Uiso 1 1 calc R . .
C68 C 0.25559(19) 0.5447(4) 0.2279(2) 0.102(2) Uani 1 1 d . . .
H68A H 0.2650 0.5929 0.2117 0.153 Uiso 1 1 calc R . .
H68B H 0.2652 0.4856 0.2199 0.153 Uiso 1 1 calc R . .
H68C H 0.2644 0.5562 0.2545 0.153 Uiso 1 1 calc R . .
C69 C 0.19339(17) 0.5073(3) 0.30893(14) 0.0660(14) Uani 1 1 d . . .
C70 C 0.1616(2) 0.4543(4) 0.29669(18) 0.0921(19) Uani 1 1 d . . .
H70 H 0.1377 0.4832 0.2922 0.111 Uiso 1 1 calc R . .
C71 C 0.1644(3) 0.3604(5) 0.2909(2) 0.118(3) Uani 1 1 d . . .
H71 H 0.1425 0.3261 0.2828 0.141 Uiso 1 1 calc R . .
C72 C 0.1983(4) 0.3187(5) 0.2970(3) 0.141(4) Uani 1 1 d . . .
H72 H 0.2001 0.2552 0.2923 0.169 Uiso 1 1 calc R . .
C73 C 0.2309(3) 0.3670(6) 0.3100(2) 0.132(3) Uani 1 1 d . . .
H73 H 0.2545 0.3366 0.3144 0.158 Uiso 1 1 calc R . .
C74 C 0.2279(2) 0.4634(4) 0.31667(18) 0.0957(19) Uani 1 1 d . . .
H74 H 0.2495 0.4969 0.3263 0.115 Uiso 1 1 calc R . .
C75 C 0.1704(3) 0.5022(6) 0.3976(2) 0.141(3) Uani 1 1 d . . .
H75A H 0.1505 0.4979 0.4160 0.170 Uiso 1 1 calc R . .
H75B H 0.1628 0.4652 0.3747 0.170 Uiso 1 1 calc R . .
C76 C 0.2046(4) 0.4771(8) 0.4135(3) 0.208(5) Uani 1 1 d . . .
H76A H 0.2246 0.5022 0.3985 0.313 Uiso 1 1 calc R . .
H76B H 0.2064 0.4104 0.4138 0.313 Uiso 1 1 calc R . .
H76C H 0.2078 0.5003 0.4397 0.313 Uiso 1 1 calc R . .
C77 C 0.1572(3) 0.6816(5) 0.4526(3) 0.143(3) Uani 1 1 d . . .
H77A H 0.1361 0.7253 0.4551 0.172 Uiso 1 1 calc R . .
H77B H 0.1482 0.6197 0.4587 0.172 Uiso 1 1 calc R . .
C78 C 0.1900(4) 0.7067(6) 0.4785(3) 0.184(5) Uani 1 1 d . . .
H78A H 0.2094 0.6593 0.4779 0.276 Uiso 1 1 calc R . .
H78B H 0.1820 0.7129 0.5045 0.276 Uiso 1 1 calc R . .
H78C H 0.2004 0.7648 0.4703 0.276 Uiso 1 1 calc R . .
C79 C 0.23212(16) 0.9344(4) 0.4112(2) 0.101(2) Uani 1 1 d . . .
H79A H 0.2413 0.9885 0.4259 0.121 Uiso 1 1 calc R . .
H79B H 0.2390 0.8797 0.4266 0.121 Uiso 1 1 calc R . .
C80 C 0.2513(2) 0.9303(6) 0.3755(3) 0.167(4) Uani 1 1 d . . .
H80A H 0.2422 0.8772 0.3606 0.251 Uiso 1 1 calc R . .
H80B H 0.2788 0.9249 0.3814 0.251 Uiso 1 1 calc R . .
H80C H 0.2459 0.9859 0.3607 0.251 Uiso 1 1 calc R . .
C81 C 0.17996(15) 1.1144(3) 0.41494(17) 0.0748(15) Uani 1 1 d . . .
H81A H 0.2014 1.1124 0.4347 0.090 Uiso 1 1 calc R . .
H81B H 0.1596 1.1517 0.4250 0.090 Uiso 1 1 calc R . .
C82 C 0.19337(19) 1.1608(4) 0.3790(2) 0.111(2) Uani 1 1 d . . .
H82A H 0.2155 1.1283 0.3705 0.167 Uiso 1 1 calc R . .
H82B H 0.2003 1.2242 0.3849 0.167 Uiso 1 1 calc R . .
H82C H 0.1729 1.1595 0.3587 0.167 Uiso 1 1 calc R . .
C83 C 0.08952(14) 1.1344(3) 0.40229(16) 0.0647(13) Uani 1 1 d . . .
C84 C 0.08199(17) 1.1739(4) 0.4376(2) 0.102(2) Uani 1 1 d . . .
H84 H 0.0772 1.1362 0.4587 0.123 Uiso 1 1 calc R . .
C85 C 0.0816(2) 1.2711(6) 0.4414(3) 0.137(3) Uani 1 1 d . . .
H85 H 0.0769 1.2986 0.4651 0.164 Uiso 1 1 calc R . .
C86 C 0.0883(2) 1.3249(5) 0.4096(4) 0.152(5) Uani 1 1 d . . .
H86 H 0.0882 1.3893 0.4120 0.183 Uiso 1 1 calc R . .
C87 C 0.0949(2) 1.2865(5) 0.3749(3) 0.129(3) Uani 1 1 d . . .
H87 H 0.0990 1.3240 0.3536 0.154 Uiso 1 1 calc R . .
C88 C 0.09551(16) 1.1903(4) 0.37140(19) 0.0867(17) Uani 1 1 d . . .
H88 H 0.1001 1.1637 0.3475 0.104 Uiso 1 1 calc R . .
C89 C 0.00228(18) 1.1177(4) 0.3747(3) 0.120(3) Uani 1 1 d . . .
H89A H -0.0166 1.1216 0.3539 0.180 Uiso 0.504(15) 1 d PR A .
H89B H 0.0237 1.1597 0.3705 0.180 Uiso 0.504(15) 1 d PR . .
H89C H -0.0247 1.1253 0.3801 0.180 Uiso 0.496(15) 1 d PR . .
H89D H 0.0175 1.1634 0.3905 0.180 Uiso 0.496(15) 1 d PR . .
C90A C -0.0170(5) 1.1577(9) 0.4123(6) 0.167(10) Uani 0.504(15) 1 d P A 1
H90A H -0.0292 1.2162 0.4060 0.251 Uiso 0.504(15) 1 calc PR A 1
H90B H 0.0027 1.1663 0.4331 0.251 Uiso 0.504(15) 1 calc PR A 1
H90C H -0.0360 1.1144 0.4204 0.251 Uiso 0.504(15) 1 calc PR A 1
C90B C 0.0077(6) 1.1335(12) 0.3299(7) 0.194(12) Uani 0.496(15) 1 d P A 2
H90D H 0.0344 1.1239 0.3250 0.291 Uiso 0.496(15) 1 calc PR A 2
H90E H 0.0003 1.1959 0.3228 0.291 Uiso 0.496(15) 1 calc PR A 2
H90F H -0.0082 1.0903 0.3147 0.291 Uiso 0.496(15) 1 calc PR A 2
C91 C -0.05028(17) 0.9422(5) 0.3674(3) 0.118(3) Uani 1 1 d . . .
H91A H -0.0593 1.0057 0.3638 0.142 Uiso 1 1 calc R . .
H91B H -0.0653 0.9135 0.3869 0.142 Uiso 1 1 calc R . .
C92 C -0.0574(2) 0.8891(7) 0.3287(3) 0.174(4) Uani 1 1 d . . .
H92A H -0.0407 0.9131 0.3100 0.261 Uiso 1 1 calc R . .
H92B H -0.0840 0.8967 0.3191 0.261 Uiso 1 1 calc R . .
H92C H -0.0521 0.8242 0.3330 0.261 Uiso 1 1 calc R . .
N1 N 0.03215(12) 0.7557(2) 0.08727(13) 0.0712(12) Uani 1 1 d . . .
H1 H 0.0486 0.7991 0.0837 0.085 Uiso 1 1 calc R . .
N2 N 0.10390(11) 0.7802(2) 0.07190(10) 0.0545(10) Uani 1 1 d . . .
N3 N 0.14786(10) 0.9306(2) 0.11521(10) 0.0535(9) Uani 1 1 d . . .
H3 H 0.1442 0.8894 0.1327 0.064 Uiso 1 1 calc R . .
N4 N 0.16461(11) 0.9096(2) 0.19268(11) 0.0582(10) Uani 1 1 d . . .
N5 N 0.17605(11) 0.7515(2) 0.27496(10) 0.0588(10) Uani 1 1 d . . .
H5 H 0.1710 0.7847 0.2948 0.071 Uiso 1 1 calc R . .
N6 N 0.18036(10) 0.7464(2) 0.35148(11) 0.0538(9) Uani 1 1 d . . .
N7 N 0.12792(11) 0.8904(2) 0.39673(11) 0.0571(10) Uani 1 1 d . . .
H7 H 0.1082 0.8542 0.3936 0.069 Uiso 1 1 calc R . .
N8 N 0.05246(11) 0.8887(2) 0.39808(12) 0.0657(11) 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'
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_3
N1 C1 C2 109.0(4) .
N1 C1 C36 118.9(4) 2
C2 C1 C36 132.0(5) 2
C3 C2 C1 107.7(4) .
C3 C2 C37 126.4(5) .
C1 C2 C37 125.9(5) .
C2 C3 C4 106.9(4) .
C2 C3 C39 123.8(5) .
C4 C3 C39 129.0(4) .
N1 C4 C5 120.4(4) .
N1 C4 C3 106.1(4) .
C5 C4 C3 133.3(4) .
C6 C5 C4 124.3(4) .
C6 C5 C41 117.8(4) .
C4 C5 C41 117.9(4) .
C5 C6 N2 119.1(4) .
C5 C6 C7 133.1(4) .
N2 C6 C7 107.8(4) .
C8 C7 C6 107.0(4) .
C8 C7 C47 123.0(5) .
C6 C7 C47 130.0(5) .
C7 C8 C9 106.6(4) .
C7 C8 C49 128.1(4) .
C9 C8 C49 124.9(5) .
N2 C9 C8 110.9(4) .
N2 C9 C10 119.9(4) .
C8 C9 C10 129.1(4) .
N3 C10 C11 107.7(4) .
N3 C10 C9 119.9(4) .
C11 C10 C9 132.3(4) .
C10 C11 C12 107.2(4) .
C10 C11 C51 124.9(5) .
C12 C11 C51 127.1(4) .
C13 C12 C11 108.0(4) .
C13 C12 C53 128.5(5) .
C11 C12 C53 123.2(4) .
N3 C13 C12 106.0(4) .
N3 C13 C14 121.1(4) .
C12 C13 C14 132.6(4) .
C15 C14 C13 123.9(4) .
C15 C14 C55 118.3(4) .
C13 C14 C55 117.7(4) .
C14 C15 N4 120.1(4) .
C14 C15 C16 130.3(4) .
N4 C15 C16 109.6(4) .
C17 C16 C15 106.4(4) .
C17 C16 C61 124.1(4) .
C15 C16 C61 129.1(4) .
C16 C17 C18 106.1(4) .
C16 C17 C63 125.7(4) .
C18 C17 C63 127.8(4) .
N4 C18 C19 120.4(4) .
N4 C18 C17 111.9(4) .
C19 C18 C17 127.6(4) .
N5 C19 C20 108.0(4) .
N5 C19 C18 121.2(4) .
C20 C19 C18 130.8(4) .
C21 C20 C19 106.8(4) .
C21 C20 C65 125.3(4) .
C19 C20 C65 127.6(4) .
C20 C21 C22 107.5(4) .
C20 C21 C67 123.0(4) .
C22 C21 C67 129.2(4) .
N5 C22 C23 121.4(4) .
N5 C22 C21 106.8(4) .
C23 C22 C21 131.7(4) .
C24 C23 C22 124.0(4) .
C24 C23 C69 120.0(4) .
C22 C23 C69 115.9(4) .
C23 C24 N6 119.6(4) .
C23 C24 C25 132.6(4) .
N6 C24 C25 107.3(4) .
C26 C25 C24 106.6(4) .
C26 C25 C75 122.6(5) .
C24 C25 C75 128.6(5) .
C25 C26 C27 107.5(5) .
C25 C26 C77 128.4(5) .
C27 C26 C77 123.6(5) .
N6 C27 C26 110.2(4) .
N6 C27 C28 119.7(4) .
C26 C27 C28 129.7(4) .
N7 C28 C29 109.2(4) .
N7 C28 C27 119.3(4) .
C29 C28 C27 131.1(4) .
C28 C29 C30 107.4(4) .
C28 C29 C79 124.6(4) .
C30 C29 C79 127.9(4) .
C29 C30 C31 106.8(4) .
C29 C30 C81 124.3(4) .
C31 C30 C81 129.0(4) .
N7 C31 C32 119.8(4) .
N7 C31 C30 106.4(4) .
C32 C31 C30 133.8(4) .
C33 C32 C31 124.0(4) .
C33 C32 C83 118.3(4) .
C31 C32 C83 117.8(4) .
C32 C33 N8 120.6(4) .
C32 C33 C34 131.1(4) .
N8 C33 C34 108.3(4) .
C35 C34 C33 107.1(4) .
C35 C34 C89 122.9(5) .
C33 C34 C89 129.9(5) .
C34 C35 C36 105.8(5) .
C34 C35 C91 127.1(5) .
C36 C35 C91 126.8(5) .
N8 C36 C35 111.0(4) .
N8 C36 C1 121.9(4) 2
C35 C36 C1 126.9(5) 2
C38 C37 C2 114.7(8) .
C3 C39 C40 113.2(6) .
C46 C41 C42 118.9(4) .
C46 C41 C5 120.5(4) .
C42 C41 C5 120.6(5) .
C41 C42 C43 120.3(6) .
C44 C43 C42 119.1(6) .
C45 C44 C43 120.8(6) .
C44 C45 C46 120.7(6) .
C41 C46 C45 120.2(5) .
C48 C47 C7 113.4(5) .
C8 C49 C50 112.8(5) .
C11 C51 C52 109.8(5) .
C54 C53 C12 113.3(5) .
C60 C55 C56 118.4(5) .
C60 C55 C14 120.9(5) .
C56 C55 C14 120.7(5) .
C55 C56 C57 120.7(6) .
C58 C57 C56 119.3(7) .
C59 C58 C57 121.2(7) .
C58 C59 C60 120.1(7) .
C55 C60 C59 120.2(6) .
C16 C61 C62 113.8(5) .
C17 C63 C64 112.7(4) .
C66 C65 C20 113.8(5) .
C21 C67 C68 112.6(4) .
C74 C69 C70 118.3(5) .
C74 C69 C23 122.1(5) .
C70 C69 C23 119.5(5) .
C71 C70 C69 121.7(7) .
C72 C71 C70 119.7(8) .
C71 C72 C73 121.4(8) .
C72 C73 C74 118.9(8) .
C69 C74 C73 119.8(7) .
C76 C75 C25 100.5(10) .
C78 C77 C26 106.4(8) .
C80 C79 C29 113.4(7) .
C30 C81 C82 113.3(5) .
C88 C83 C84 119.6(5) .
C88 C83 C32 122.0(5) .
C84 C83 C32 118.4(5) .
C83 C84 C85 119.6(7) .
C86 C85 C84 118.9(8) .
C87 C86 C85 121.5(8) .
C86 C87 C88 119.3(8) .
C83 C88 C87 121.0(7) .
C34 C89 C90B 106.5(9) .
C34 C89 C90A 107.6(8) .
C90B C89 C90A 145.1(10) .
C35 C91 C92 112.8(6) .
C1 N1 C4 110.2(4) .
C9 N2 C6 107.6(4) .
C10 N3 C13 111.1(3) .
C18 N4 C15 105.8(3) .
C19 N5 C22 110.9(4) .
C27 N6 C24 108.3(3) .
C28 N7 C31 110.2(4) .
C36 N8 C33 107.7(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.337(6) .
C1 C2 1.403(6) .
C1 C36 1.467(6) 2
C2 C3 1.385(6) .
C2 C37 1.498(8) .
C3 C4 1.443(7) .
C3 C39 1.486(7) .
C4 N1 1.383(5) .
C4 C5 1.401(6) .
C5 C6 1.398(6) .
C5 C41 1.496(6) .
C6 N2 1.402(5) .
C6 C7 1.436(6) .
C7 C8 1.378(6) .
C7 C47 1.510(6) .
C8 C9 1.424(6) .
C8 C49 1.500(7) .
C9 N2 1.329(5) .
C9 C10 1.462(6) .
C10 N3 1.355(5) .
C10 C11 1.392(6) .
C11 C12 1.410(6) .
C11 C51 1.490(7) .
C12 C13 1.403(6) .
C12 C53 1.503(6) .
C13 N3 1.380(5) .
C13 C14 1.417(6) .
C14 C15 1.389(6) .
C14 C55 1.488(6) .
C15 N4 1.402(5) .
C15 C16 1.458(6) .
C16 C17 1.361(6) .
C16 C61 1.500(6) .
C17 C18 1.461(6) .
C17 C63 1.499(6) .
C18 N4 1.329(5) .
C18 C19 1.451(6) .
C19 N5 1.341(5) .
C19 C20 1.440(6) .
C20 C21 1.394(6) .
C20 C65 1.492(7) .
C21 C22 1.432(6) .
C21 C67 1.498(6) .
C22 N5 1.381(5) .
C22 C23 1.413(6) .
C23 C24 1.399(6) .
C23 C69 1.483(6) .
C24 N6 1.398(5) .
C24 C25 1.425(6) .
C25 C26 1.360(7) .
C25 C75 1.659(9) .
C26 C27 1.413(6) .
C26 C77 1.596(9) .
C27 N6 1.305(5) .
C27 C28 1.467(6) .
C28 N7 1.325(5) .
C28 C29 1.395(6) .
C29 C30 1.393(6) .
C29 C79 1.504(7) .
C30 C31 1.426(6) .
C30 C81 1.501(6) .
C31 N7 1.385(5) .
C31 C32 1.412(6) .
C32 C33 1.392(6) .
C32 C83 1.488(6) .
C33 N8 1.396(5) .
C33 C34 1.437(7) .
C34 C35 1.380(7) .
C34 C89 1.517(7) .
C35 C36 1.445(7) .
C35 C91 1.498(8) .
C36 N8 1.324(6) .
C36 C1 1.467(6) 2
C37 C38 1.391(12) .
C39 C40 1.499(10) .
C41 C46 1.382(7) .
C41 C42 1.382(7) .
C42 C43 1.396(8) .
C43 C44 1.385(10) .
C44 C45 1.337(9) .
C45 C46 1.389(7) .
C47 C48 1.496(8) .
C49 C50 1.517(10) .
C51 C52 1.601(11) .
C53 C54 1.450(9) .
C55 C60 1.364(7) .
C55 C56 1.367(7) .
C56 C57 1.399(8) .
C57 C58 1.337(9) .
C58 C59 1.338(9) .
C59 C60 1.395(7) .
C61 C62 1.506(8) .
C63 C64 1.507(7) .
C65 C66 1.475(8) .
C67 C68 1.505(7) .
C69 C74 1.361(7) .
C69 C70 1.379(7) .
C70 C71 1.370(8) .
C71 C72 1.321(11) .
C72 C73 1.373(11) .
C73 C74 1.410(9) .
C75 C76 1.319(11) .
C77 C78 1.437(12) .
C79 C80 1.439(10) .
C81 C82 1.508(8) .
C83 C88 1.360(7) .
C83 C84 1.382(7) .
C84 C85 1.405(9) .
C85 C86 1.372(12) .
C86 C87 1.349(13) .
C87 C88 1.388(8) .
C89 C90B 1.58(2) .
C89 C90A 1.605(17) .
C91 C92 1.538(11) .
