#------------------------------------------------------------------------------
#$Date: 2023-01-12 12:22:49 +0200 (Thu, 12 Jan 2023) $
#$Revision: 280302 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106452.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_8106452
loop_
_publ_author_name
'Wu, Xiangxiang'
'Zai, Yanbing'
_publ_section_title
;
 Crystal structure of tripropylammonium
 2′-carboxy-[1,1′-biphenyl]-2-carboxylate --
 [1,1′-biphenyl]-2,2′-dicarboxylic acid (2/1), C60H72N2O12
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              117
_journal_page_last               119
_journal_paper_doi               10.1515/ncrs-2016-0177
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         '2(C9 H22 N), C14 H10 O4, 2(C14 H9 O4)'
_chemical_formula_sum            'C60 H72 N2 O12'
_chemical_formula_weight         1013.20
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_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
_cell_angle_alpha                113.198(3)
_cell_angle_beta                 95.632(4)
_cell_angle_gamma                91.114(3)
_cell_formula_units_Z            1
_cell_length_a                   9.6569(4)
_cell_length_b                   10.9361(4)
_cell_length_c                   13.8551(6)
_cell_measurement_reflns_used    4230
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.81
_cell_volume                     1335.72(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9438
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         7449
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0828P)²+0.5222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                6838
_reflns_number_total             7449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0177_suppl.cif
_cod_data_source_block           test
_cod_original_cell_volume        1335.72(9)
_cod_original_sg_symbol_Hall     'P1   '
_cod_original_sg_symbol_H-M      'P1   '
_cod_database_code               8106452
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_symmetry_equiv_pos_as_xyz
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9301(3) 0.3645(3) 0.6838(3) 0.0363(7) Uani 1 1 d D . .
H1 H 1.0229(18) 0.343(5) 0.683(4) 0.054 Uiso 1 1 d D . .
C1 C 0.1031(3) 0.9018(3) 0.9611(3) 0.0293(7) Uani 1 1 d . . .
O1 O 0.1222(3) 1.0297(3) 0.81658(19) 0.0375(6) Uani 1 1 d D . .
H1A H 0.127(5) 1.073(4) 0.777(3) 0.056 Uiso 1 1 d D . .
N2 N 0.4457(3) 0.6138(3) 0.1896(3) 0.0353(7) Uani 1 1 d D . .
H2 H 0.3531(19) 0.580(4) 0.176(4) 0.053 Uiso 1 1 d D . .
C2 C -0.0040(3) 0.9684(3) 0.9306(3) 0.0284(7) Uani 1 1 d . . .
O2 O -0.0821(3) 1.1129(4) 0.8510(3) 0.0668(10) Uani 1 1 d . . .
O3 O 0.2223(3) 1.1652(2) 1.06002(19) 0.0364(6) Uani 1 1 d D . .
H3 H 0.216(5) 1.2468(18) 1.103(3) 0.055 Uiso 1 1 d D . .
C3 C -0.1343(4) 0.9670(4) 0.9641(3) 0.0360(8) Uani 1 1 d . . .
H3A H -0.2062 1.0123 0.9428 0.043 Uiso 1 1 calc R . .
C4 C -0.1622(4) 0.9009(4) 1.0278(3) 0.0394(9) Uani 1 1 d . . .
H4A H -0.2522 0.9009 1.0501 0.047 Uiso 1 1 calc R . .
O4 O 0.4331(3) 1.2140(3) 1.0317(4) 0.0820(13) Uani 1 1 d . . .
O5 O 1.2268(3) 0.3222(3) 0.65534(19) 0.0379(6) Uani 1 1 d . . .
C5 C -0.0576(4) 0.8353(4) 1.0586(3) 0.0416(9) Uani 1 1 d . . .
H5A H -0.0756 0.7892 1.1020 0.050 Uiso 1 1 calc R . .
O6 O 1.1329(3) 0.1754(3) 0.7062(2) 0.0445(6) Uani 1 1 d . . .
C6 C 0.0726(4) 0.8362(4) 1.0266(3) 0.0373(8) Uani 1 1 d . . .
H6A H 0.1438 0.7915 1.0494 0.045 Uiso 1 1 calc R . .
O7 O 1.4457(3) 0.4005(2) 0.59524(19) 0.0360(6) Uani 1 1 d D . .
H7 H 1.374(3) 0.379(5) 0.619(4) 0.054 Uiso 1 1 d D . .
C7 C 0.0088(3) 1.0437(3) 0.8610(3) 0.0317(8) Uani 1 1 d . . .
O8 O 1.5544(3) 0.3667(2) 0.4545(2) 0.0435(7) Uani 1 1 d . . .
C8 C 0.2457(4) 0.8869(3) 0.9261(3) 0.0291(7) Uani 1 1 d . . .
C9 C 0.3516(3) 0.9882(3) 0.9543(3) 0.0296(7) Uani 1 1 d . . .
O9 O 0.2186(3) 0.4265(3) 0.1603(2) 0.0446(7) Uani 1 1 d . . .
C10 C 0.4815(4) 0.9550(4) 0.9196(3) 0.0354(8) Uani 1 1 d . . .
H10A H 0.5539 1.0234 0.9400 0.042 Uiso 1 1 calc R . .
O10 O 0.1261(3) 0.6217(2) 0.22056(19) 0.0389(6) Uani 1 1 d . . .
C11 C 0.5092(4) 0.8259(4) 0.8563(3) 0.0429(9) Uani 1 1 d . . .
H11A H 0.5981 0.8061 0.8321 0.051 Uiso 1 1 calc R . .
O11 O -0.0903(3) 0.7472(2) 0.28426(19) 0.0359(6) Uani 1 1 d D . .
H11 H -0.009(2) 0.716(5) 0.273(4) 0.054 Uiso 1 1 d D . .
C12 C 0.4045(4) 0.7270(4) 0.8294(3) 0.0423(9) Uani 1 1 d . . .
H12A H 0.4209 0.6375 0.7863 0.051 Uiso 1 1 calc R . .
O12 O -0.1907(3) 0.8537(3) 0.4288(2) 0.0413(6) Uani 1 1 d . . .
C13 C 0.2767(4) 0.7574(4) 0.8646(3) 0.0379(8) Uani 1 1 d . . .
H13A H 0.2066 0.6874 0.8464 0.045 Uiso 1 1 calc R . .
C14 C 0.3399(3) 1.1327(4) 1.0204(3) 0.0349(8) Uani 1 1 d . . .
C15 C 1.4168(3) 0.1068(3) 0.5566(3) 0.0269(7) Uani 1 1 d . . .
C16 C 1.3631(4) 0.1457(3) 0.6550(3) 0.0304(7) Uani 1 1 d . . .
C17 C 1.4394(4) 0.1222(4) 0.7365(3) 0.0393(9) Uani 1 1 d . . .
H17A H 1.4014 0.1421 0.8013 0.047 Uiso 1 1 calc R . .
C18 C 1.5672(4) 0.0712(4) 0.7246(3) 0.0405(9) Uani 1 1 d . . .
H18A H 1.6199 0.0612 0.7824 0.049 Uiso 1 1 calc R . .
C19 C 1.6208(4) 0.0335(4) 0.6281(3) 0.0358(8) Uani 1 1 d . . .
H19A H 1.7091 -0.0037 0.6192 0.043 Uiso 1 1 calc R . .
C20 C 1.5442(3) 0.0509(3) 0.5453(3) 0.0301(7) Uani 1 1 d . . .
H20A H 1.5800 0.0238 0.4790 0.036 Uiso 1 1 calc R . .
C21 C 1.2323(4) 0.2175(4) 0.6742(3) 0.0352(8) Uani 1 1 d . . .
C22 C 1.3319(3) 0.1182(3) 0.4644(2) 0.0276(7) Uani 1 1 d . . .
C23 C 1.3566(4) 0.2211(3) 0.4317(3) 0.0281(7) Uani 1 1 d . . .
C24 C 1.2826(4) 0.2203(4) 0.3391(3) 0.0352(8) Uani 1 1 d . . .
H24A H 1.3021 0.2891 0.3158 0.042 Uiso 1 1 calc R . .
C25 C 1.1813(4) 0.1199(4) 0.2815(3) 0.0370(8) Uani 1 1 d . . .
H25A H 1.1294 0.1210 0.2200 0.044 Uiso 1 1 calc R . .
C26 C 1.1560(4) 0.0175(4) 0.3141(3) 0.0359(8) Uani 1 1 d . . .
H26A H 1.0867 -0.0519 0.2748 0.043 Uiso 1 1 calc R . .
C27 C 1.2317(4) 0.0168(3) 0.4034(3) 0.0309(7) Uani 1 1 d . . .
H27A H 1.2150 -0.0549 0.4241 0.037 Uiso 1 1 calc R . .
C28 C 1.4608(4) 0.3349(3) 0.4944(3) 0.0325(8) Uani 1 1 d . . .
C29 C -0.0607(3) 0.4890(3) 0.3132(3) 0.0268(7) Uani 1 1 d . . .
C30 C -0.0103(4) 0.4362(3) 0.2148(3) 0.0327(8) Uani 1 1 d . . .
C31 C -0.0864(4) 0.3345(4) 0.1318(3) 0.0413(9) Uani 1 1 d . . .
H31A H -0.0503 0.2972 0.0656 0.050 Uiso 1 1 calc R . .
C32 C -0.2144(4) 0.2855(4) 0.1427(3) 0.0421(9) Uani 1 1 d . . .
H32A H -0.2669 0.2164 0.0845 0.051 Uiso 1 1 calc R . .
C33 C -0.2650(4) 0.3396(3) 0.2410(3) 0.0374(8) Uani 1 1 d . . .
H33A H -0.3530 0.3076 0.2497 0.045 Uiso 1 1 calc R . .
C34 C -0.1884(4) 0.4388(3) 0.3250(3) 0.0326(8) Uani 1 1 d . . .
H34A H -0.2231 0.4735 0.3918 0.039 Uiso 1 1 calc R . .
C35 C 0.1205(4) 0.4974(4) 0.1973(3) 0.0347(8) Uani 1 1 d . . .
C36 C 0.0240(3) 0.5920(3) 0.4092(3) 0.0269(7) Uani 1 1 d . . .
C37 C 0.0011(4) 0.7274(3) 0.4456(3) 0.0285(7) Uani 1 1 d . . .
C38 C 0.0752(4) 0.8170(3) 0.5392(3) 0.0346(8) Uani 1 1 d . . .
H38A H 0.0576 0.9089 0.5649 0.041 Uiso 1 1 calc R . .
C39 C 0.1746(4) 0.7722(4) 0.5949(3) 0.0387(8) Uani 1 1 d . . .
H39A H 0.2264 0.8338 0.6578 0.046 Uiso 1 1 calc R . .
C40 C 0.1983(4) 0.6387(4) 0.5593(3) 0.0361(8) Uani 1 1 d . . .
H40A H 0.2663 0.6083 0.5975 0.043 Uiso 1 1 calc R . .
C41 C 0.1227(4) 0.5488(3) 0.4676(3) 0.0320(8) Uani 1 1 d . . .
H41A H 0.1382 0.4566 0.4440 0.038 Uiso 1 1 calc R . .
C42 C -0.1015(4) 0.7826(3) 0.3874(3) 0.0302(7) Uani 1 1 d . . .
C43 C 0.8673(5) 0.3564(4) 0.7749(3) 0.0467(10) Uani 1 1 d . . .
H43A H 0.8774 0.2655 0.7728 0.056 Uiso 1 1 calc R . .
H43B H 0.7662 0.3685 0.7656 0.056 Uiso 1 1 calc R . .
C44 C 0.9272(5) 0.4558(5) 0.8837(3) 0.0547(11) Uani 1 1 d . . .
H44A H 0.9118 0.5470 0.8880 0.066 Uiso 1 1 calc R . .
H44B H 0.8755 0.4420 0.9372 0.066 Uiso 1 1 calc R . .
C45 C 1.0802(6) 0.4467(6) 0.9111(4) 0.0683(13) Uani 1 1 d . . .
H45A H 1.1110 0.5144 0.9818 0.102 Uiso 1 1 calc R . .
H45B H 1.1328 0.4617 0.8593 0.102 Uiso 1 1 calc R . .
H45C H 1.0964 0.3579 0.9098 0.102 Uiso 1 1 calc R . .
C46 C 0.9376(4) 0.5030(3) 0.6862(3) 0.0363(8) Uani 1 1 d . . .
H46A H 0.9887 0.5022 0.6274 0.044 Uiso 1 1 calc R . .
H46B H 0.9926 0.5626 0.7531 0.044 Uiso 1 1 calc R . .
C47 C 0.7978(4) 0.5614(4) 0.6774(3) 0.0411(9) Uani 1 1 d . . .
H47A H 0.7408 0.5027 0.6112 0.049 Uiso 1 1 calc R . .
H47B H 0.7470 0.5672 0.7376 0.049 Uiso 1 1 calc R . .
C48 C 0.8199(5) 0.6989(4) 0.6777(3) 0.0484(10) Uani 1 1 d . . .
H48A H 0.7293 0.7359 0.6720 0.073 Uiso 1 1 calc R . .
H48B H 0.8692 0.6927 0.6175 0.073 Uiso 1 1 calc R . .
H48C H 0.8755 0.7570 0.7436 0.073 Uiso 1 1 calc R . .
C49 C 0.8572(4) 0.2621(4) 0.5823(3) 0.0367(8) Uani 1 1 d . . .
H49A H 0.8586 0.1740 0.5867 0.044 Uiso 1 1 calc R . .
H49B H 0.7584 0.2834 0.5758 0.044 Uiso 1 1 calc R . .
C50 C 0.9181(4) 0.2517(4) 0.4839(3) 0.0389(8) Uani 1 1 d . . .
H50A H 1.0166 0.2289 0.4884 0.047 Uiso 1 1 calc R . .
H50B H 0.9158 0.3386 0.4773 0.047 Uiso 1 1 calc R . .
C51 C 0.8360(4) 0.1455(4) 0.3878(3) 0.0423(9) Uani 1 1 d . . .
H51A H 0.8764 0.1394 0.3240 0.063 Uiso 1 1 calc R . .
H51B H 0.7388 0.1688 0.3830 0.063 Uiso 1 1 calc R . .
H51C H 0.8394 0.0594 0.3941 0.063 Uiso 1 1 calc R . .
C52 C 0.5143(4) 0.6182(4) 0.2925(3) 0.0368(8) Uani 1 1 d . . .
H52A H 0.6117 0.6550 0.3027 0.044 Uiso 1 1 calc R . .
H52B H 0.5178 0.5258 0.2882 0.044 Uiso 1 1 calc R . .
C53 C 0.4443(4) 0.6999(4) 0.3890(3) 0.0391(8) Uani 1 1 d . . .
H53A H 0.3465 0.6648 0.3803 0.047 Uiso 1 1 calc R . .
H53B H 0.4434 0.7938 0.3966 0.047 Uiso 1 1 calc R . .
C54 C 0.5231(5) 0.6932(4) 0.4880(3) 0.0455(9) Uani 1 1 d . . .
H54A H 0.4771 0.7457 0.5500 0.068 Uiso 1 1 calc R . .
H54B H 0.6194 0.7295 0.4971 0.068 Uiso 1 1 calc R . .
H54C H 0.5233 0.6003 0.4804 0.068 Uiso 1 1 calc R . .
C55 C 0.4227(4) 0.7497(4) 0.1895(3) 0.0366(8) Uani 1 1 d . . .
H55A H 0.3681 0.7991 0.2482 0.044 Uiso 1 1 calc R . .
H55B H 0.3664 0.7386 0.1226 0.044 Uiso 1 1 calc R . .
C56 C 0.5554(4) 0.8320(4) 0.2011(3) 0.0415(9) Uani 1 1 d . . .
H56A H 0.6100 0.7851 0.1418 0.050 Uiso 1 1 calc R . .
H56B H 0.6127 0.8444 0.2679 0.050 Uiso 1 1 calc R . .
C57 C 0.5205(5) 0.9665(4) 0.2013(3) 0.0471(10) Uani 1 1 d . . .
H57A H 0.6069 1.0198 0.2094 0.071 Uiso 1 1 calc R . .
H57B H 0.4667 1.0128 0.2602 0.071 Uiso 1 1 calc R . .
H57C H 0.4653 0.9539 0.1345 0.071 Uiso 1 1 calc R . .
C58 C 0.5257(4) 0.5284(4) 0.1007(3) 0.0440(9) Uani 1 1 d . . .
H58A H 0.5350 0.4404 0.1046 0.053 Uiso 1 1 calc R . .
H58B H 0.6208 0.5707 0.1118 0.053 Uiso 1 1 calc R . .
C59 C 0.4600(5) 0.5068(5) -0.0091(3) 0.0539(11) Uani 1 1 d . . .
H59A H 0.3731 0.4492 -0.0263 0.065 Uiso 1 1 calc R . .
H59B H 0.4350 0.5937 -0.0101 0.065 Uiso 1 1 calc R . .
C60 C 0.5555(7) 0.4435(7) -0.0918(5) 0.0852(17) Uani 1 1 d . . .
H60A H 0.5089 0.4317 -0.1613 0.128 Uiso 1 1 calc R . .
H60B H 0.5789 0.3565 -0.0923 0.128 Uiso 1 1 calc R . .
H60C H 0.6410 0.5010 -0.0759 0.128 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'
O O 0.0106 0.0060 '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
C43 N1 C46 113.1(3) . .
C43 N1 C49 109.7(3) . .
C46 N1 C49 113.7(3) . .
C43 N1 H1 112(3) . .
C46 N1 H1 103(3) . .
C49 N1 H1 105(3) . .
C2 C1 C6 117.5(3) . .
C2 C1 C8 126.3(3) . .
C6 C1 C8 116.1(3) . .
C7 O1 H1A 114(3) . .
C52 N2 C55 113.5(3) . .
C52 N2 C58 109.6(3) . .
C55 N2 C58 113.0(3) . .
C52 N2 H2 112(3) . .
C55 N2 H2 99(3) . .
C58 N2 H2 109(3) . .
C3 C2 C1 120.0(3) . .
C3 C2 C7 114.9(3) . .
C1 C2 C7 125.1(3) . .
C14 O3 H3 118(3) . .
C4 C3 C2 121.5(4) . .
C4 C3 H3A 119.3 . .
C2 C3 H3A 119.3 . .
C5 C4 C3 119.1(3) . .
C5 C4 H4A 120.5 . .
C3 C4 H4A 120.5 . .
C6 C5 C4 120.3(4) . .
C6 C5 H5A 119.9 . .
C4 C5 H5A 119.9 . .
C5 C6 C1 121.7(4) . .
C5 C6 H6A 119.2 . .
C1 C6 H6A 119.2 . .
C28 O7 H7 118(3) . .
O2 C7 O1 124.2(3) . .
O2 C7 C2 120.2(3) . .
O1 C7 C2 115.6(3) . .
C13 C8 C9 117.8(3) . .
C13 C8 C1 115.6(3) . .
C9 C8 C1 126.5(3) . .
C10 C9 C8 118.8(3) . .
C10 C9 C14 115.1(3) . .
C8 C9 C14 126.1(3) . .
C11 C10 C9 122.4(3) . .
C11 C10 H10A 118.8 . .
C9 C10 H10A 118.8 . .
C12 C11 C10 118.3(4) . .
C12 C11 H11A 120.9 . .
C10 C11 H11A 120.9 . .
C42 O11 H11 107(3) . .
C13 C12 C11 120.1(4) . .
C13 C12 H12A 120.0 . .
C11 C12 H12A 120.0 . .
C12 C13 C8 122.5(3) . .
C12 C13 H13A 118.7 . .
C8 C13 H13A 118.7 . .
O4 C14 O3 122.8(4) . .
O4 C14 C9 120.8(3) . .
O3 C14 C9 116.4(3) . .
C20 C15 C16 119.0(3) . .
C20 C15 C22 120.7(3) . .
C16 C15 C22 120.2(3) . .
C17 C16 C15 118.6(3) . .
C17 C16 C21 120.3(3) . .
C15 C16 C21 121.0(3) . .
C18 C17 C16 121.2(3) . .
C18 C17 H17A 119.4 . .
C16 C17 H17A 119.4 . .
C17 C18 C19 120.2(3) . .
C17 C18 H18A 119.9 . .
C19 C18 H18A 119.9 . .
C20 C19 C18 119.3(3) . .
C20 C19 H19A 120.4 . .
C18 C19 H19A 120.4 . .
C15 C20 C19 121.5(3) . .
C15 C20 H20A 119.2 . .
C19 C20 H20A 119.2 . .
O6 C21 O5 122.0(3) . .
O6 C21 C16 121.2(3) . .
O5 C21 C16 116.8(3) . .
C27 C22 C23 118.2(3) . .
C27 C22 C15 119.1(3) . .
C23 C22 C15 122.6(3) . .
C22 C23 C24 120.2(3) . .
C22 C23 C28 121.2(3) . .
C24 C23 C28 118.6(3) . .
C25 C24 C23 120.3(3) . .
C25 C24 H24A 119.8 . .
C23 C24 H24A 119.8 . .
C24 C25 C26 119.6(3) . .
C24 C25 H25A 120.2 . .
C26 C25 H25A 120.2 . .
C27 C26 C25 119.8(3) . .
C27 C26 H26A 120.1 . .
C25 C26 H26A 120.1 . .
C26 C27 C22 121.9(3) . .
C26 C27 H27A 119.1 . .
C22 C27 H27A 119.1 . .
O8 C28 O7 121.3(3) . .
O8 C28 C23 121.9(3) . .
O7 C28 C23 116.8(3) . .
C34 C29 C30 119.1(3) . .
C34 C29 C36 118.8(3) . .
C30 C29 C36 121.9(3) . .
C31 C30 C29 119.7(3) . .
C31 C30 C35 120.0(3) . .
C29 C30 C35 120.0(3) . .
C30 C31 C32 121.3(3) . .
C30 C31 H31A 119.3 . .
C32 C31 H31A 119.3 . .
C31 C32 C33 118.7(3) . .
C31 C32 H32A 120.7 . .
C33 C32 H32A 120.7 . .
C34 C33 C32 120.5(3) . .
C34 C33 H33A 119.8 . .
C32 C33 H33A 119.8 . .
C33 C34 C29 120.7(3) . .
C33 C34 H34A 119.7 . .
C29 C34 H34A 119.7 . .
O9 C35 O10 122.2(3) . .
O9 C35 C30 120.5(3) . .
O10 C35 C30 117.3(3) . .
C37 C36 C41 118.8(3) . .
C37 C36 C29 122.4(3) . .
C41 C36 C29 118.6(3) . .
C36 C37 C38 120.1(3) . .
C36 C37 C42 122.4(3) . .
C38 C37 C42 117.5(3) . .
C39 C38 C37 120.1(3) . .
C39 C38 H38A 120.0 . .
C37 C38 H38A 120.0 . .
C40 C39 C38 120.2(3) . .
C40 C39 H39A 119.9 . .
C38 C39 H39A 119.9 . .
C39 C40 C41 119.9(3) . .
C39 C40 H40A 120.0 . .
C41 C40 H40A 120.0 . .
C40 C41 C36 120.9(3) . .
C40 C41 H41A 119.6 . .
C36 C41 H41A 119.6 . .
O12 C42 O11 120.7(3) . .
O12 C42 C37 123.1(3) . .
O11 C42 C37 116.2(3) . .
N1 C43 C44 116.3(4) . .
N1 C43 H43A 108.2 . .
C44 C43 H43A 108.2 . .
N1 C43 H43B 108.2 . .
C44 C43 H43B 108.2 . .
H43A C43 H43B 107.4 . .
C45 C44 C43 114.5(4) . .
C45 C44 H44A 108.6 . .
C43 C44 H44A 108.6 . .
C45 C44 H44B 108.6 . .
C43 C44 H44B 108.6 . .
H44A C44 H44B 107.6 . .
C44 C45 H45A 109.5 . .
C44 C45 H45B 109.5 . .
H45A C45 H45B 109.5 . .
C44 C45 H45C 109.5 . .
H45A C45 H45C 109.5 . .
H45B C45 H45C 109.5 . .
N1 C46 C47 115.3(3) . .
N1 C46 H46A 108.5 . .
C47 C46 H46A 108.5 . .
N1 C46 H46B 108.5 . .
C47 C46 H46B 108.5 . .
H46A C46 H46B 107.5 . .
C48 C47 C46 109.9(3) . .
C48 C47 H47A 109.7 . .
C46 C47 H47A 109.7 . .
C48 C47 H47B 109.7 . .
C46 C47 H47B 109.7 . .
H47A C47 H47B 108.2 . .
C47 C48 H48A 109.5 . .
C47 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C47 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
C50 C49 N1 115.3(3) . .
C50 C49 H49A 108.5 . .
N1 C49 H49A 108.5 . .
C50 C49 H49B 108.5 . .
N1 C49 H49B 108.5 . .
H49A C49 H49B 107.5 . .
C49 C50 C51 110.1(3) . .
C49 C50 H50A 109.6 . .
C51 C50 H50A 109.6 . .
C49 C50 H50B 109.6 . .
C51 C50 H50B 109.6 . .
H50A C50 H50B 108.2 . .
C50 C51 H51A 109.5 . .
C50 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C50 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
N2 C52 C53 115.4(3) . .
N2 C52 H52A 108.4 . .
C53 C52 H52A 108.4 . .
N2 C52 H52B 108.4 . .
C53 C52 H52B 108.4 . .
H52A C52 H52B 107.5 . .
C52 C53 C54 109.8(3) . .
C52 C53 H53A 109.7 . .
C54 C53 H53A 109.7 . .
C52 C53 H53B 109.7 . .
C54 C53 H53B 109.7 . .
H53A C53 H53B 108.2 . .
C53 C54 H54A 109.5 . .
C53 C54 H54B 109.5 . .
H54A C54 H54B 109.5 . .
C53 C54 H54C 109.5 . .
H54A C54 H54C 109.5 . .
H54B C54 H54C 109.5 . .
N2 C55 C56 114.1(3) . .
N2 C55 H55A 108.7 . .
C56 C55 H55A 108.7 . .
N2 C55 H55B 108.7 . .
C56 C55 H55B 108.7 . .
H55A C55 H55B 107.6 . .
C55 C56 C57 109.8(3) . .
C55 C56 H56A 109.7 . .
C57 C56 H56A 109.7 . .
C55 C56 H56B 109.7 . .
C57 C56 H56B 109.7 . .
H56A C56 H56B 108.2 . .
C56 C57 H57A 109.5 . .
C56 C57 H57B 109.5 . .
H57A C57 H57B 109.5 . .
C56 C57 H57C 109.5 . .
H57A C57 H57C 109.5 . .
H57B C57 H57C 109.5 . .
N2 C58 C59 114.7(4) . .
N2 C58 H58A 108.6 . .
C59 C58 H58A 108.6 . .
N2 C58 H58B 108.6 . .
C59 C58 H58B 108.6 . .
H58A C58 H58B 107.6 . .
C60 C59 C58 112.3(4) . .
C60 C59 H59A 109.1 . .
C58 C59 H59A 109.1 . .
C60 C59 H59B 109.1 . .
C58 C59 H59B 109.1 . .
H59A C59 H59B 107.9 . .
C59 C60 H60A 109.5 . .
C59 C60 H60B 109.5 . .
H60A C60 H60B 109.5 . .
C59 C60 H60C 109.5 . .
H60A C60 H60C 109.5 . .
H60B C60 H60C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C43 1.485(5) .
N1 C46 1.502(5) .
N1 C49 1.504(5) .
N1 H1 0.932(10) .
C1 C2 1.402(5) .
C1 C6 1.408(5) .
C1 C8 1.495(5) .
O1 C7 1.291(4) .
O1 H1A 0.858(10) .
N2 C52 1.495(5) .
N2 C55 1.507(5) .
N2 C58 1.515(5) .
N2 H2 0.935(10) .
C2 C3 1.385(5) .
C2 C7 1.506(5) .
O2 C7 1.203(5) .
O3 C14 1.304(4) .
O3 H3 0.862(10) .
C3 C4 1.384(5) .
C3 H3A 0.9500 .
C4 C5 1.379(6) .
C4 H4A 0.9500 .
O4 C14 1.207(5) .
O5 C21 1.272(5) .
C5 C6 1.374(6) .
C5 H5A 0.9500 .
O6 C21 1.247(4) .
C6 H6A 0.9500 .
O7 C28 1.320(4) .
O7 H7 0.861(10) .
O8 C28 1.216(4) .
C8 C13 1.392(5) .
C8 C9 1.400(5) .
C9 C10 1.391(5) .
C9 C14 1.496(5) .
O9 C35 1.254(5) .
C10 C11 1.385(6) .
C10 H10A 0.9500 .
O10 C35 1.266(5) .
C11 C12 1.377(6) .
C11 H11A 0.9500 .
O11 C42 1.342(4) .
O11 H11 0.867(10) .
C12 C13 1.370(6) .
C12 H12A 0.9500 .
O12 C42 1.203(4) .
C13 H13A 0.9500 .
C15 C20 1.379(5) .
C15 C16 1.413(5) .
C15 C22 1.498(5) .
C16 C17 1.399(5) .
C16 C21 1.492(5) .
C17 C18 1.362(6) .
C17 H17A 0.9500 .
C18 C19 1.391(6) .
C18 H18A 0.9500 .
C19 C20 1.382(5) .
C19 H19A 0.9500 .
C20 H20A 0.9500 .
C22 C27 1.393(5) .
C22 C23 1.393(4) .
C23 C24 1.404(5) .
C23 C28 1.498(5) .
C24 C25 1.383(5) .
C24 H24A 0.9500 .
C25 C26 1.389(5) .
C25 H25A 0.9500 .
C26 C27 1.377(5) .
C26 H26A 0.9500 .
C27 H27A 0.9500 .
C29 C34 1.390(5) .
C29 C30 1.397(5) .
C29 C36 1.509(5) .
C30 C31 1.376(5) .
C30 C35 1.502(5) .
C31 C32 1.383(5) .
C31 H31A 0.9500 .
C32 C33 1.396(6) .
C32 H32A 0.9500 .
C33 C34 1.372(5) .
C33 H33A 0.9500 .
C34 H34A 0.9500 .
C36 C37 1.393(4) .
C36 C41 1.397(5) .
C37 C38 1.394(5) .
C37 C42 1.499(5) .
C38 C39 1.389(5) .
C38 H38A 0.9500 .
C39 C40 1.376(5) .
C39 H39A 0.9500 .
C40 C41 1.386(5) .
C40 H40A 0.9500 .
C41 H41A 0.9500 .
C43 C44 1.517(6) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C44 C45 1.504(7) .
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C45 H45A 0.9800 .
C45 H45B 0.9800 .
C45 H45C 0.9800 .
C46 C47 1.519(5) .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C47 C48 1.512(6) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
C49 C50 1.502(5) .
C49 H49A 0.9900 .
C49 H49B 0.9900 .
C50 C51 1.513(5) .
C50 H50A 0.9900 .
C50 H50B 0.9900 .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
C52 C53 1.517(5) .
C52 H52A 0.9900 .
C52 H52B 0.9900 .
C53 C54 1.531(6) .
C53 H53A 0.9900 .
C53 H53B 0.9900 .
C54 H54A 0.9800 .
C54 H54B 0.9800 .
C54 H54C 0.9800 .
C55 C56 1.510(5) .
C55 H55A 0.9900 .
C55 H55B 0.9900 .
C56 C57 1.513(6) .
C56 H56A 0.9900 .
C56 H56B 0.9900 .
C57 H57A 0.9800 .
C57 H57B 0.9800 .
C57 H57C 0.9800 .
C58 C59 1.515(6) .
C58 H58A 0.9900 .
C58 H58B 0.9900 .
C59 C60 1.499(8) .
C59 H59A 0.9900 .
C59 H59B 0.9900 .
C60 H60A 0.9800 .
C60 H60B 0.9800 .
C60 H60C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.6(5) . . . .
C8 C1 C2 C3 175.9(3) . . . .
C6 C1 C2 C7 -180.0(3) . . . .
C8 C1 C2 C7 -3.5(5) . . . .
C1 C2 C3 C4 0.1(5) . . . .
C7 C2 C3 C4 179.5(3) . . . .
C2 C3 C4 C5 0.0(5) . . . .
C3 C4 C5 C6 0.3(5) . . . .
C4 C5 C6 C1 -0.9(5) . . . .
C2 C1 C6 C5 1.0(5) . . . .
C8 C1 C6 C5 -175.9(3) . . . .
C3 C2 C7 O2 10.9(5) . . . .
C1 C2 C7 O2 -169.7(4) . . . .
C3 C2 C7 O1 -170.2(3) . . . .
C1 C2 C7 O1 9.2(5) . . . .
C2 C1 C8 C13 -114.2(4) . . . .
C6 C1 C8 C13 62.3(4) . . . .
C2 C1 C8 C9 69.9(5) . . . .
C6 C1 C8 C9 -113.6(4) . . . .
C13 C8 C9 C10 0.3(5) . . . .
C1 C8 C9 C10 176.1(3) . . . .
C13 C8 C9 C14 -179.4(3) . . . .
C1 C8 C9 C14 -3.6(5) . . . .
C8 C9 C10 C11 1.3(5) . . . .
C14 C9 C10 C11 -179.0(3) . . . .
C9 C10 C11 C12 -1.6(6) . . . .
C10 C11 C12 C13 0.3(6) . . . .
C11 C12 C13 C8 1.3(6) . . . .
C9 C8 C13 C12 -1.6(5) . . . .
C1 C8 C13 C12 -177.9(3) . . . .
C10 C9 C14 O4 7.6(6) . . . .
C8 C9 C14 O4 -172.7(4) . . . .
C10 C9 C14 O3 -175.5(3) . . . .
C8 C9 C14 O3 4.2(5) . . . .
C20 C15 C16 C17 -2.0(5) . . . .
C22 C15 C16 C17 174.1(3) . . . .
C20 C15 C16 C21 174.5(3) . . . .
C22 C15 C16 C21 -9.5(5) . . . .
C15 C16 C17 C18 4.4(5) . . . .
C21 C16 C17 C18 -172.1(4) . . . .
C16 C17 C18 C19 -4.0(6) . . . .
C17 C18 C19 C20 1.2(5) . . . .
C16 C15 C20 C19 -0.7(5) . . . .
C22 C15 C20 C19 -176.8(3) . . . .
C18 C19 C20 C15 1.1(5) . . . .
C17 C16 C21 O6 -57.5(5) . . . .
C15 C16 C21 O6 126.1(4) . . . .
C17 C16 C21 O5 123.3(4) . . . .
C15 C16 C21 O5 -53.1(4) . . . .
C20 C15 C22 C27 93.0(4) . . . .
C16 C15 C22 C27 -83.1(4) . . . .
C20 C15 C22 C23 -81.8(4) . . . .
C16 C15 C22 C23 102.2(4) . . . .
C27 C22 C23 C24 -0.7(5) . . . .
C15 C22 C23 C24 174.1(3) . . . .
C27 C22 C23 C28 178.8(3) . . . .
C15 C22 C23 C28 -6.5(5) . . . .
C22 C23 C24 C25 2.2(5) . . . .
C28 C23 C24 C25 -177.3(3) . . . .
C23 C24 C25 C26 -1.9(5) . . . .
C24 C25 C26 C27 0.1(6) . . . .
C25 C26 C27 C22 1.4(5) . . . .
C23 C22 C27 C26 -1.1(5) . . . .
C15 C22 C27 C26 -176.1(3) . . . .
C22 C23 C28 O8 126.5(4) . . . .
C24 C23 C28 O8 -54.1(5) . . . .
C22 C23 C28 O7 -54.2(5) . . . .
C24 C23 C28 O7 125.2(3) . . . .
C34 C29 C30 C31 -0.9(5) . . . .
C36 C29 C30 C31 174.5(3) . . . .
C34 C29 C30 C35 174.2(3) . . . .
C36 C29 C30 C35 -10.4(5) . . . .
C29 C30 C31 C32 1.9(6) . . . .
C35 C30 C31 C32 -173.2(4) . . . .
C30 C31 C32 C33 -1.2(6) . . . .
C31 C32 C33 C34 -0.4(6) . . . .
C32 C33 C34 C29 1.3(5) . . . .
C30 C29 C34 C33 -0.7(5) . . . .
C36 C29 C34 C33 -176.3(3) . . . .
C31 C30 C35 O9 -57.2(5) . . . .
C29 C30 C35 O9 127.7(4) . . . .
C31 C30 C35 O10 122.2(4) . . . .
C29 C30 C35 O10 -52.8(5) . . . .
C34 C29 C36 C37 -83.8(4) . . . .
C30 C29 C36 C37 100.7(4) . . . .
C34 C29 C36 C41 91.9(4) . . . .
C30 C29 C36 C41 -83.6(4) . . . .
C41 C36 C37 C38 -0.5(5) . . . .
C29 C36 C37 C38 175.2(3) . . . .
C41 C36 C37 C42 179.3(3) . . . .
C29 C36 C37 C42 -5.0(5) . . . .
C36 C37 C38 C39 1.7(5) . . . .
C42 C37 C38 C39 -178.1(3) . . . .
C37 C38 C39 C40 -1.5(5) . . . .
C38 C39 C40 C41 0.0(5) . . . .
C39 C40 C41 C36 1.2(5) . . . .
C37 C36 C41 C40 -0.9(5) . . . .
C29 C36 C41 C40 -176.8(3) . . . .
C36 C37 C42 O12 128.3(4) . . . .
C38 C37 C42 O12 -51.9(4) . . . .
C36 C37 C42 O11 -50.9(4) . . . .
C38 C37 C42 O11 128.9(3) . . . .
C46 N1 C43 C44 -50.6(5) . . . .
C49 N1 C43 C44 -178.7(4) . . . .
N1 C43 C44 C45 -59.9(5) . . . .
C43 N1 C46 C47 -63.8(4) . . . .
C49 N1 C46 C47 62.2(4) . . . .
N1 C46 C47 C48 -178.4(3) . . . .
C43 N1 C49 C50 -175.2(3) . . . .
C46 N1 C49 C50 57.0(4) . . . .
N1 C49 C50 C51 179.9(3) . . . .
C55 N2 C52 C53 53.1(4) . . . .
C58 N2 C52 C53 -179.5(3) . . . .
N2 C52 C53 C54 178.7(3) . . . .
C52 N2 C55 C56 65.7(4) . . . .
C58 N2 C55 C56 -59.9(4) . . . .
N2 C55 C56 C57 -179.3(3) . . . .
C52 N2 C58 C59 175.4(3) . . . .
C55 N2 C58 C59 -57.0(4) . . . .
N2 C58 C59 C60 169.5(4) . . . .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{b5c315ab-db6e-459b-b6be-a2b58d6e9ce6} y y y
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{b5c315ab-db6e-459b-b6be-a2b58d6e9ce6} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
CE
