#------------------------------------------------------------------------------
#$Date: 2025-11-29 20:12:08 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303698 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/11/7251162.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_7251162
loop_
_publ_author_name
'Yamada, Shinji'
'Akazawa, Rika'
'Chida, Moemi'
_publ_section_title
;
 Supramolecular dual-synthon in cocrystals of 1-azaanthracene and
 naphthols: cooperation between hydrogen bonds and cation--π interactions
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              7491
_journal_page_last               7497
_journal_paper_doi               10.1039/D5CE01015B
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '2(C13 H9 N), C10 H8 O2'
_chemical_formula_sum            'C36 H26 N2 O2'
_chemical_formula_weight         518.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2025-10-23 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                99.423(4)
_cell_angle_beta                 97.130(3)
_cell_angle_gamma                102.165(4)
_cell_formula_units_Z            4
_cell_length_a                   7.1764(4)
_cell_length_b                   14.0408(8)
_cell_length_c                   26.7227(13)
_cell_measurement_reflns_used    8539
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.29
_cell_volume                     2561.3(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29539
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.227
_diffrn_reflns_theta_min         3.283
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1088.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.76
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     737
_refine_ls_number_reflns         9193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0872
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1785P)²+0.7082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2860
_refine_ls_wR_factor_ref         0.3224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5467
_reflns_number_total             9193
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d5ce01015b2.cif
_cod_data_source_block           compound-4
_cod_depositor_comments
'Adding full bibliography for 7251160--7251164.cif.'
_cod_database_code               7251162
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2653(3) 0.41004(18) 0.18668(9) 0.0442(6) Uani 1 1 d . . . . .
O2 O 0.8145(3) 0.92133(18) 0.18213(9) 0.0454(6) Uani 1 1 d . . . . .
O3 O 0.7425(4) 0.0926(2) 0.31357(10) 0.0598(8) Uani 1 1 d . . . . .
O4 O 1.2416(5) 0.5973(2) 0.31744(10) 0.0626(8) Uani 1 1 d . . . . .
N1 N 1.0698(5) 0.0755(2) 0.37090(11) 0.0554(9) Uani 1 1 d . . . . .
N2 N 1.5670(5) 0.5778(3) 0.37438(11) 0.0595(9) Uani 1 1 d . . . . .
N4 N 0.3103(4) 0.5537(2) 0.12826(10) 0.0368(7) Uani 1 1 d . . . . .
N6 N 0.8713(4) 1.06629(19) 0.12641(10) 0.0366(7) Uani 1 1 d . . . . .
C7 C 0.2952(4) 0.5390(2) 0.07524(12) 0.0342(7) Uani 1 1 d . . . . .
C8 C 0.3740(4) 0.6176(2) 0.05065(12) 0.0340(7) Uani 1 1 d . . . . .
C9 C 0.2601(4) 0.5073(2) -0.03287(12) 0.0342(7) Uani 1 1 d . . . . .
C10 C 0.8240(4) 1.0477(2) 0.07304(12) 0.0325(7) Uani 1 1 d . . . . .
C12 C 0.7092(4) 1.0043(2) -0.03442(12) 0.0331(7) Uani 1 1 d . . . . .
C14 C 0.1792(4) 0.4287(2) -0.00799(12) 0.0336(7) Uani 1 1 d . . . . .
C15 C 1.1085(5) 0.0958(2) 0.42402(12) 0.0380(8) Uani 1 1 d . . . . .
C16 C 1.6073(5) 0.5971(2) 0.42727(12) 0.0378(8) Uani 1 1 d . . . . .
C17 C 0.3577(4) 0.5994(2) -0.00274(12) 0.0366(8) Uani 1 1 d . . . . .
H17 H 0.4144 0.6509 -0.0191 0.044 Uiso 1 1 calc R U . . .
C18 C 1.1209(5) 0.7883(2) 0.24952(11) 0.0359(8) Uani 1 1 d . . . . .
C19 C 0.7995(4) 1.1246(2) 0.04620(12) 0.0328(7) Uani 1 1 d . . . . .
C20 C 0.7389(4) 0.9274(2) -0.00740(12) 0.0344(7) Uani 1 1 d . . . . .
C21 C 0.2014(4) 0.4460(2) 0.04565(12) 0.0357(8) Uani 1 1 d . . . . .
H21 H 0.1517 0.3935 0.0622 0.043 Uiso 1 1 calc R U . . .
C22 C 0.6155(5) 0.4535(2) 0.20677(11) 0.0361(8) Uani 1 1 d . . . . .
H22 H 0.6218 0.5107 0.1918 0.043 Uiso 1 1 calc R U . . .
C23 C 0.4342(5) 0.3902(2) 0.20724(11) 0.0362(8) Uani 1 1 d . . . . .
C24 C 0.7778(5) 0.3479(3) 0.25070(12) 0.0391(8) Uani 1 1 d . . . . .
C25 C 1.3078(5) 0.8473(3) 0.24935(12) 0.0395(8) Uani 1 1 d . . . . .
C26 C 0.4250(5) 0.3079(2) 0.22868(11) 0.0361(7) Uani 1 1 d . . . . .
H26 H 0.3027 0.2661 0.2290 0.043 Uiso 1 1 calc R U . . .
C27 C 0.5959(5) 0.2840(2) 0.25051(11) 0.0359(8) Uani 1 1 d . . . . .
C28 C 0.7966(4) 0.9506(2) 0.04596(12) 0.0365(8) Uani 1 1 d . . . . .
H28 H 0.8175 0.8998 0.0640 0.044 Uiso 1 1 calc R U . . .
C29 C 0.9565(5) 0.8157(2) 0.22642(12) 0.0364(7) Uani 1 1 d . . . . .
H29 H 0.8308 0.7773 0.2268 0.044 Uiso 1 1 calc R U . . .
C30 C 0.4623(5) 0.7120(2) 0.08249(13) 0.0399(8) Uani 1 1 d . . . . .
H30 H 0.5186 0.7658 0.0676 0.048 Uiso 1 1 calc R U . . .
C31 C 0.9773(5) 0.8972(2) 0.20357(11) 0.0363(8) Uani 1 1 d . . . . .
C32 C 0.3884(5) 0.6430(3) 0.15496(13) 0.0411(8) Uani 1 1 d . . . . .
H32 H 0.3930 0.6532 0.1912 0.049 Uiso 1 1 calc R U . . .
C33 C 0.0779(5) 0.3355(2) -0.03959(12) 0.0398(8) Uani 1 1 d . . . . .
H33 H 0.0224 0.2826 -0.0240 0.048 Uiso 1 1 calc R U . . .
C34 C 0.2363(5) 0.4884(3) -0.08742(12) 0.0406(8) Uani 1 1 d . . . . .
H34 H 0.2901 0.5398 -0.1042 0.049 Uiso 1 1 calc R U . . .
C35 C 0.7411(4) 1.1012(2) -0.00709(12) 0.0347(7) Uani 1 1 d . . . . .
H35 H 0.7228 1.1525 -0.0250 0.042 Uiso 1 1 calc R U . . .
C36 C 0.8340(4) 1.2224(2) 0.07558(13) 0.0384(8) Uani 1 1 d . . . . .
H36 H 0.8208 1.2760 0.0589 0.046 Uiso 1 1 calc R U . . .
C37 C 0.4662(5) 0.7253(2) 0.13389(13) 0.0410(8) Uani 1 1 d . . . . .
H37 H 0.5203 0.7887 0.1553 0.049 Uiso 1 1 calc R U . . .
C38 C 0.6458(5) 0.9782(3) -0.08868(12) 0.0396(8) Uani 1 1 d . . . . .
H38 H 0.6241 1.0284 -0.1071 0.048 Uiso 1 1 calc R U . . .
C39 C 1.1628(5) 0.9545(2) 0.20265(12) 0.0386(8) Uani 1 1 d . . . . .
H39 H 1.1763 1.0107 0.1866 0.046 Uiso 1 1 calc R U . . .
C40 C 0.0598(5) 0.3212(3) -0.09175(13) 0.0424(8) Uani 1 1 d . . . . .
H40 H -0.0067 0.2583 -0.1121 0.051 Uiso 1 1 calc R U . . .
C41 C 0.7573(6) 0.1771(3) 0.29351(12) 0.0462(9) Uani 1 1 d . . . . .
C42 C 0.7082(5) 0.8287(2) -0.03629(13) 0.0411(8) Uani 1 1 d . . . . .
H42 H 0.7298 0.7770 -0.0191 0.049 Uiso 1 1 calc R U . . .
C43 C 0.1390(5) 0.3991(3) -0.11605(13) 0.0425(8) Uani 1 1 d . . . . .
H43 H 0.1238 0.3886 -0.1525 0.051 Uiso 1 1 calc R U . . .
C44 C 1.1756(5) 0.1305(3) 0.53204(13) 0.0466(9) Uani 1 1 d . . . . .
C45 C 0.9002(5) 1.1580(2) 0.15082(13) 0.0401(8) Uani 1 1 d . . . . .
H45 H 0.9335 1.1708 0.1872 0.048 Uiso 1 1 calc R U . . .
C46 C 1.1047(5) 0.7038(3) 0.27305(12) 0.0403(8) Uani 1 1 d . . . . .
H46 H 0.9806 0.6633 0.2730 0.048 Uiso 1 1 calc R U . . .
C47 C 0.7815(5) 0.4320(3) 0.22791(12) 0.0409(8) Uani 1 1 d . . . . .
H47 H 0.9025 0.4748 0.2272 0.049 Uiso 1 1 calc R U . . .
C48 C 0.5906(5) 0.1978(3) 0.27207(12) 0.0406(8) Uani 1 1 d . . . . .
H48 H 0.4697 0.1539 0.2716 0.049 Uiso 1 1 calc R U . . .
C49 C 0.6159(5) 0.8837(3) -0.11447(13) 0.0421(8) Uani 1 1 d . . . . .
H49 H 0.5727 0.8680 -0.1506 0.051 Uiso 1 1 calc R U . . .
C50 C 1.3235(5) 0.9297(3) 0.22473(12) 0.0412(8) Uani 1 1 d . . . . .
H50 H 1.4479 0.9685 0.2235 0.049 Uiso 1 1 calc R U . . .
C51 C 1.6775(5) 0.6309(3) 0.53519(13) 0.0474(9) Uani 1 1 d . . . . .
C52 C 1.2665(6) 0.6801(3) 0.29580(12) 0.0477(9) Uani 1 1 d . . . . .
C53 C 0.8856(5) 1.2392(2) 0.12716(13) 0.0425(8) Uani 1 1 d . . . . .
H53 H 0.9115 1.3045 0.1471 0.051 Uiso 1 1 calc R U . . .
C54 C 0.6486(5) 0.8078(3) -0.08790(13) 0.0442(9) Uani 1 1 d . . . . .
H54 H 0.6288 0.7417 -0.1064 0.053 Uiso 1 1 calc R U . . .
C55 C 1.1947(6) 0.0437(2) 0.34557(13) 0.0456(9) Uani 1 1 d . . . . .
H55 H 1.1648 0.0285 0.3091 0.055 Uiso 1 1 calc R U . . .
C56 C 0.9471(5) 0.3238(3) 0.27353(13) 0.0490(9) Uani 1 1 d . . . . .
H56 H 1.0698 0.3663 0.2742 0.059 Uiso 1 1 calc R U . . .
C57 C 1.4513(5) 0.7397(3) 0.29646(13) 0.0532(10) Uani 1 1 d . . . . .
H57 H 1.5627 0.7235 0.3128 0.064 Uiso 1 1 calc R U . . .
C58 C 1.0708(6) 0.1753(3) 0.61363(13) 0.0504(10) Uani 1 1 d . . . . .
H58 H 1.0924 0.1850 0.6501 0.060 Uiso 1 1 calc R U . . .
C59 C 0.9375(5) 0.2414(3) 0.29441(13) 0.0528(10) Uani 1 1 d . . . . .
H59 H 1.0526 0.2272 0.3097 0.063 Uiso 1 1 calc R U . . .
C60 C 1.5091(5) 0.6455(3) 0.50965(13) 0.0495(10) Uani 1 1 d . . . . .
C61 C 1.5759(6) 0.6750(3) 0.61716(13) 0.0511(10) Uani 1 1 d . . . . .
H61 H 1.5983 0.6840 0.6536 0.061 Uiso 1 1 calc R U . . .
C62 C 1.6915(6) 0.5468(2) 0.34855(13) 0.0465(9) Uani 1 1 d . . . . .
H62 H 1.6601 0.5319 0.3121 0.056 Uiso 1 1 calc R U . . .
C63 C 1.4707(5) 0.8203(3) 0.27384(12) 0.0483(9) Uani 1 1 d . . . . .
H63 H 1.5964 0.8596 0.2744 0.058 Uiso 1 1 calc R U . . .
C64 C 1.0071(5) 0.1443(3) 0.50577(14) 0.0510(10) Uani 1 1 d . . . . .
C65 C 1.2779(5) 0.0825(4) 0.45042(15) 0.0653(13) Uani 1 1 d . . . . .
C66 C 1.7771(5) 0.5843(4) 0.45304(15) 0.0665(13) Uani 1 1 d . . . . .
C67 C 1.2012(7) 0.1477(4) 0.58653(15) 0.0857(18) Uani 1 1 d . . . . .
H67 H 1.3172 0.1391 0.6046 0.103 Uiso 1 1 calc R U . . .
C68 C 1.4786(7) 0.6281(4) 0.45618(15) 0.0896(19) Uani 1 1 d . . . . .
H68 H 1.3627 0.6381 0.4388 0.108 Uiso 1 1 calc R U . . .
C69 C 0.9785(7) 0.1267(4) 0.45230(15) 0.0854(18) Uani 1 1 d . . . . .
H69 H 0.8631 0.1366 0.4346 0.102 Uiso 1 1 calc R U . . .
C70 C 1.7060(8) 0.6482(4) 0.58982(15) 0.0928(19) Uani 1 1 d . . . . .
H70 H 1.8230 0.6402 0.6076 0.111 Uiso 1 1 calc R U . . .
C71 C 1.8650(6) 0.5343(4) 0.37051(17) 0.0904(18) Uani 1 1 d . . . . .
H71 H 1.9528 0.5126 0.3500 0.108 Uiso 1 1 calc R U . . .
C72 C 1.3675(6) 0.0308(4) 0.36829(17) 0.0904(18) Uani 1 1 d . . . . .
H72 H 1.4555 0.0082 0.3482 0.109 Uiso 1 1 calc R U . . .
C73 C 0.9066(7) 0.1890(5) 0.58781(17) 0.099(2) Uani 1 1 d . . . . .
H73 H 0.8128 0.2098 0.6064 0.119 Uiso 1 1 calc R U . . .
C74 C 1.4117(7) 0.6893(5) 0.59223(17) 0.097(2) Uani 1 1 d . . . . .
H74 H 1.3190 0.7101 0.6112 0.116 Uiso 1 1 calc R U . . .
C75 C 1.3058(7) 0.1018(6) 0.50326(17) 0.124(3) Uani 1 1 d . . . . .
H75 H 1.4238 0.0947 0.5210 0.149 Uiso 1 1 calc R U . . .
C76 C 1.8074(7) 0.6032(6) 0.50590(17) 0.127(3) Uani 1 1 d . . . . .
H76 H 1.9265 0.5967 0.5232 0.153 Uiso 1 1 calc R U . . .
C77 C 1.4081(7) 0.0510(7) 0.41955(19) 0.161(4) Uani 1 1 d . . . . .
H77 H 1.5285 0.0439 0.4358 0.193 Uiso 1 1 calc R U . . .
C78 C 1.3787(8) 0.6742(7) 0.54030(18) 0.159(4) Uani 1 1 d . . . . .
H78 H 1.2607 0.6836 0.5238 0.191 Uiso 1 1 calc R U . . .
C79 C 1.9065(7) 0.5536(7) 0.42170(19) 0.166(4) Uani 1 1 d . . . . .
H79 H 2.0273 0.5464 0.4376 0.199 Uiso 1 1 calc R U . . .
C80 C 0.8756(8) 0.1734(7) 0.53587(18) 0.159(4) Uani 1 1 d . . . . .
H80 H 0.7582 0.1827 0.5190 0.190 Uiso 1 1 calc R U . . .
H1 H 0.292(6) 0.468(3) 0.1651(15) 0.071(13) Uiso 1 1 d . . . . .
H2 H 0.842(6) 0.975(3) 0.1601(16) 0.073(13) Uiso 1 1 d . . . . .
H3 H 0.868(7) 0.085(3) 0.3340(19) 0.101(17) Uiso 1 1 d . . . . .
H4 H 1.357(7) 0.589(3) 0.3362(19) 0.089(16) Uiso 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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 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
_geom_angle_publ_flag
C23 O1 H1 111(2) . . ?
C31 O2 H2 114(2) . . ?
C41 O3 H3 116(3) . . ?
C52 O4 H4 114(3) . . ?
C55 N1 C15 118.9(3) . . ?
C62 N2 C16 118.8(3) . . ?
C32 N4 C7 118.2(3) . . ?
C45 N6 C10 117.5(3) . . ?
N4 C7 C21 119.3(3) . . ?
N4 C7 C8 120.9(3) . . ?
C21 C7 C8 119.8(3) . . ?
C17 C8 C30 123.4(3) . . ?
C17 C8 C7 119.1(3) . . ?
C30 C8 C7 117.5(3) . . ?
C17 C9 C34 122.4(3) . . ?
C17 C9 C14 119.0(3) . . ?
C34 C9 C14 118.6(3) . . ?
N6 C10 C28 118.6(3) . . ?
N6 C10 C19 121.4(3) . . ?
C28 C10 C19 120.0(3) . . ?
C35 C12 C38 122.3(3) . . ?
C35 C12 C20 119.3(3) . . ?
C38 C12 C20 118.4(3) . . ?
C21 C14 C33 122.7(3) . . ?
C21 C14 C9 119.3(3) . . ?
C33 C14 C9 118.1(3) . . ?
C69 C15 N1 120.9(3) . . ?
C69 C15 C65 117.9(3) . . ?
N1 C15 C65 121.2(3) . . ?
C68 C16 N2 121.0(3) . . ?
C68 C16 C66 117.7(3) . . ?
N2 C16 C66 121.3(3) . . ?
C8 C17 C9 121.6(3) . . ?
C8 C17 H17 119.2 . . ?
C9 C17 H17 119.2 . . ?
C29 C18 C25 119.0(3) . . ?
C29 C18 C46 122.0(3) . . ?
C25 C18 C46 118.9(3) . . ?
C35 C19 C10 119.2(3) . . ?
C35 C19 C36 123.2(3) . . ?
C10 C19 C36 117.5(3) . . ?
C28 C20 C42 122.2(3) . . ?
C28 C20 C12 119.5(3) . . ?
C42 C20 C12 118.3(3) . . ?
C7 C21 C14 121.1(3) . . ?
C7 C21 H21 119.4 . . ?
C14 C21 H21 119.4 . . ?
C47 C22 C23 119.9(3) . . ?
C47 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C26 C23 O1 118.7(3) . . ?
C26 C23 C22 120.1(3) . . ?
O1 C23 C22 121.2(3) . . ?
C47 C24 C27 118.3(3) . . ?
C47 C24 C56 123.3(3) . . ?
C27 C24 C56 118.4(3) . . ?
C50 C25 C63 122.9(3) . . ?
C50 C25 C18 118.8(3) . . ?
C63 C25 C18 118.3(3) . . ?
C23 C26 C27 120.9(3) . . ?
C23 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C48 C27 C24 118.9(3) . . ?
C48 C27 C26 122.0(3) . . ?
C24 C27 C26 119.1(3) . . ?
C10 C28 C20 120.7(3) . . ?
C10 C28 H28 119.7 . . ?
C20 C28 H28 119.7 . . ?
C31 C29 C18 120.5(3) . . ?
C31 C29 H29 119.7 . . ?
C18 C29 H29 119.7 . . ?
C37 C30 C8 120.1(3) . . ?
C37 C30 H30 119.9 . . ?
C8 C30 H30 119.9 . . ?
O2 C31 C29 118.5(3) . . ?
O2 C31 C39 121.1(3) . . ?
C29 C31 C39 120.3(3) . . ?
N4 C32 C37 124.7(3) . . ?
N4 C32 H32 117.7 . . ?
C37 C32 H32 117.7 . . ?
C40 C33 C14 121.0(3) . . ?
C40 C33 H33 119.5 . . ?
C14 C33 H33 119.5 . . ?
C43 C34 C9 121.6(3) . . ?
C43 C34 H34 119.2 . . ?
C9 C34 H34 119.2 . . ?
C12 C35 C19 121.3(3) . . ?
C12 C35 H35 119.3 . . ?
C19 C35 H35 119.3 . . ?
C53 C36 C19 120.1(3) . . ?
C53 C36 H36 120.0 . . ?
C19 C36 H36 120.0 . . ?
C30 C37 C32 118.5(3) . . ?
C30 C37 H37 120.8 . . ?
C32 C37 H37 120.8 . . ?
C49 C38 C12 121.4(3) . . ?
C49 C38 H38 119.3 . . ?
C12 C38 H38 119.3 . . ?
C50 C39 C31 120.2(3) . . ?
C50 C39 H39 119.9 . . ?
C31 C39 H39 119.9 . . ?
C33 C40 C43 120.7(3) . . ?
C33 C40 H40 119.7 . . ?
C43 C40 H40 119.7 . . ?
O3 C41 C48 118.1(4) . . ?
O3 C41 C59 121.7(3) . . ?
C48 C41 C59 120.2(3) . . ?
C54 C42 C20 121.0(3) . . ?
C54 C42 H42 119.5 . . ?
C20 C42 H42 119.5 . . ?
C34 C43 C40 120.1(3) . . ?
C34 C43 H43 120.0 . . ?
C40 C43 H43 120.0 . . ?
C75 C44 C64 117.2(3) . . ?
C75 C44 C67 124.7(3) . . ?
C64 C44 C67 118.1(3) . . ?
N6 C45 C53 124.8(3) . . ?
N6 C45 H45 117.6 . . ?
C53 C45 H45 117.6 . . ?
C52 C46 C18 120.7(3) . . ?
C52 C46 H46 119.7 . . ?
C18 C46 H46 119.7 . . ?
C22 C47 C24 121.7(3) . . ?
C22 C47 H47 119.2 . . ?
C24 C47 H47 119.2 . . ?
C41 C48 C27 120.9(3) . . ?
C41 C48 H48 119.6 . . ?
C27 C48 H48 119.6 . . ?
C38 C49 C54 120.3(3) . . ?
C38 C49 H49 119.9 . . ?
C54 C49 H49 119.9 . . ?
C39 C50 C25 121.1(3) . . ?
C39 C50 H50 119.4 . . ?
C25 C50 H50 119.4 . . ?
C76 C51 C60 117.3(3) . . ?
C76 C51 C70 124.6(3) . . ?
C60 C51 C70 118.1(3) . . ?
O4 C52 C46 117.9(4) . . ?
O4 C52 C57 121.7(3) . . ?
C46 C52 C57 120.3(3) . . ?
C36 C53 C45 118.6(3) . . ?
C36 C53 H53 120.7 . . ?
C45 C53 H53 120.7 . . ?
C42 C54 C49 120.6(3) . . ?
C42 C54 H54 119.7 . . ?
C49 C54 H54 119.7 . . ?
N1 C55 C72 123.9(4) . . ?
N1 C55 H55 118.0 . . ?
C72 C55 H55 118.0 . . ?
C59 C56 C24 121.4(4) . . ?
C59 C56 H56 119.3 . . ?
C24 C56 H56 119.3 . . ?
C63 C57 C52 120.1(3) . . ?
C63 C57 H57 119.9 . . ?
C52 C57 H57 119.9 . . ?
C67 C58 C73 118.3(4) . . ?
C67 C58 H58 120.8 . . ?
C73 C58 H58 120.8 . . ?
C56 C59 C41 120.2(3) . . ?
C56 C59 H59 119.9 . . ?
C41 C59 H59 119.9 . . ?
C51 C60 C68 118.7(3) . . ?
C51 C60 C78 116.4(4) . . ?
C68 C60 C78 124.9(4) . . ?
C70 C61 C74 118.9(4) . . ?
C70 C61 H61 120.6 . . ?
C74 C61 H61 120.6 . . ?
N2 C62 C71 124.1(4) . . ?
N2 C62 H62 118.0 . . ?
C71 C62 H62 118.0 . . ?
C57 C63 C25 121.6(4) . . ?
C57 C63 H63 119.2 . . ?
C25 C63 H63 119.2 . . ?
C44 C64 C69 118.9(3) . . ?
C44 C64 C80 116.3(4) . . ?
C69 C64 C80 124.8(4) . . ?
C75 C65 C15 118.4(3) . . ?
C75 C65 C77 125.8(4) . . ?
C15 C65 C77 115.8(4) . . ?
C76 C66 C16 118.5(4) . . ?
C76 C66 C79 125.7(4) . . ?
C16 C66 C79 115.8(4) . . ?
C58 C67 C44 123.3(4) . . ?
C58 C67 H67 118.3 . . ?
C44 C67 H67 118.3 . . ?
C16 C68 C60 123.3(3) . . ?
C16 C68 H68 118.3 . . ?
C60 C68 H68 118.3 . . ?
C15 C69 C64 123.2(3) . . ?
C15 C69 H69 118.4 . . ?
C64 C69 H69 118.4 . . ?
C61 C70 C51 123.0(4) . . ?
C61 C70 H70 118.5 . . ?
C51 C70 H70 118.5 . . ?
C79 C71 C62 117.7(4) . . ?
C79 C71 H71 121.2 . . ?
C62 C71 H71 121.2 . . ?
C77 C72 C55 117.9(4) . . ?
C77 C72 H72 121.0 . . ?
C55 C72 H72 121.0 . . ?
C80 C73 C58 120.4(4) . . ?
C80 C73 H73 119.8 . . ?
C58 C73 H73 119.8 . . ?
C61 C74 C78 120.2(4) . . ?
C61 C74 H74 119.9 . . ?
C78 C74 H74 119.9 . . ?
C44 C75 C65 124.5(4) . . ?
C44 C75 H75 117.8 . . ?
C65 C75 H75 117.8 . . ?
C51 C76 C66 124.3(4) . . ?
C51 C76 H76 117.8 . . ?
C66 C76 H76 117.8 . . ?
C72 C77 C65 122.2(4) . . ?
C72 C77 H77 118.9 . . ?
C65 C77 H77 118.9 . . ?
C74 C78 C60 123.4(4) . . ?
C74 C78 H78 118.3 . . ?
C60 C78 H78 118.3 . . ?
C71 C79 C66 122.3(4) . . ?
C71 C79 H79 118.9 . . ?
C66 C79 H79 118.9 . . ?
C73 C80 C64 123.4(4) . . ?
C73 C80 H80 118.3 . . ?
C64 C80 H80 118.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C23 1.369(4) . ?
O1 H1 1.07(4) . ?
O2 C31 1.369(4) . ?
O2 H2 1.03(4) . ?
O3 C41 1.369(4) . ?
O3 H3 1.02(5) . ?
O4 C52 1.370(4) . ?
O4 H4 0.96(5) . ?
N1 C55 1.296(4) . ?
N1 C15 1.382(4) . ?
N2 C62 1.297(4) . ?
N2 C16 1.377(4) . ?
N4 C32 1.306(4) . ?
N4 C7 1.385(4) . ?
N6 C45 1.306(4) . ?
N6 C10 1.392(4) . ?
C7 C21 1.394(4) . ?
C7 C8 1.427(4) . ?
C8 C17 1.393(4) . ?
C8 C30 1.423(4) . ?
C9 C17 1.396(4) . ?
C9 C34 1.420(4) . ?
C9 C14 1.437(4) . ?
C10 C28 1.397(4) . ?
C10 C19 1.419(4) . ?
C12 C35 1.393(4) . ?
C12 C38 1.427(4) . ?
C12 C20 1.430(4) . ?
C14 C21 1.397(4) . ?
C14 C33 1.428(4) . ?
C15 C69 1.367(5) . ?
C15 C65 1.391(5) . ?
C16 C68 1.369(5) . ?
C16 C66 1.385(5) . ?
C17 H17 0.9500 . ?
C18 C29 1.418(4) . ?
C18 C25 1.421(5) . ?
C18 C46 1.421(4) . ?
C19 C35 1.397(4) . ?
C19 C36 1.420(4) . ?
C20 C28 1.398(4) . ?
C20 C42 1.429(4) . ?
C21 H21 0.9500 . ?
C22 C47 1.367(4) . ?
C22 C23 1.415(4) . ?
C22 H22 0.9500 . ?
C23 C26 1.364(4) . ?
C24 C47 1.412(5) . ?
C24 C27 1.418(5) . ?
C24 C56 1.422(4) . ?
C25 C50 1.413(5) . ?
C25 C63 1.420(4) . ?
C26 C27 1.421(4) . ?
C26 H26 0.9500 . ?
C27 C48 1.418(4) . ?
C28 H28 0.9500 . ?
C29 C31 1.373(4) . ?
C29 H29 0.9500 . ?
C30 C37 1.352(4) . ?
C30 H30 0.9500 . ?
C31 C39 1.409(5) . ?
C32 C37 1.408(5) . ?
C32 H32 0.9500 . ?
C33 C40 1.361(4) . ?
C33 H33 0.9500 . ?
C34 C43 1.353(5) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C53 1.350(4) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C49 1.352(5) . ?
C38 H38 0.9500 . ?
C39 C50 1.366(4) . ?
C39 H39 0.9500 . ?
C40 C43 1.415(5) . ?
C40 H40 0.9500 . ?
C41 C48 1.370(5) . ?
C41 C59 1.408(5) . ?
C42 C54 1.356(4) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C75 1.365(5) . ?
C44 C64 1.387(5) . ?
C44 C67 1.419(5) . ?
C45 C53 1.408(4) . ?
C45 H45 0.9500 . ?
C46 C52 1.372(5) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C54 1.416(5) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C76 1.366(5) . ?
C51 C60 1.383(5) . ?
C51 C70 1.422(5) . ?
C52 C57 1.408(6) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 C72 1.373(5) . ?
C55 H55 0.9500 . ?
C56 C59 1.357(5) . ?
C56 H56 0.9500 . ?
C57 C63 1.358(5) . ?
C57 H57 0.9500 . ?
C58 C67 1.334(6) . ?
C58 C73 1.356(6) . ?
C58 H58 0.9500 . ?
C59 H59 0.9500 . ?
C60 C68 1.391(5) . ?
C60 C78 1.397(5) . ?
C61 C70 1.332(6) . ?
C61 C74 1.349(6) . ?
C61 H61 0.9500 . ?
C62 C71 1.368(6) . ?
C62 H62 0.9500 . ?
C63 H63 0.9500 . ?
C64 C69 1.391(5) . ?
C64 C80 1.395(6) . ?
C65 C75 1.374(6) . ?
C65 C77 1.412(6) . ?
C66 C76 1.375(6) . ?
C66 C79 1.411(6) . ?
C67 H67 0.9500 . ?
C68 H68 0.9500 . ?
C69 H69 0.9500 . ?
C70 H70 0.9500 . ?
C71 C79 1.333(6) . ?
C71 H71 0.9500 . ?
C72 C77 1.334(6) . ?
C72 H72 0.9500 . ?
C73 C80 1.352(6) . ?
C73 H73 0.9500 . ?
C74 C78 1.352(6) . ?
C74 H74 0.9500 . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
C77 H77 0.9500 . ?
C78 H78 0.9500 . ?
C79 H79 0.9500 . ?
C80 H80 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N4 . . . 2.737(4) 1.07(4) 1.67(4) 174(3) no
O2 H2 N6 . . . 2.705(4) 1.03(5) 1.68(5) 175(4) no
O3 H3 N1 . . . 2.718(5) 1.02(5) 1.69(5) 177(5) no
O4 H4 N2 . . . 2.715(5) 0.96(5) 1.76(5) 176(5) no
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
_geom_torsion_publ_flag
C32 N4 C7 C21 -175.9(3) . . . . ?
C32 N4 C7 C8 4.0(4) . . . . ?
N4 C7 C8 C17 179.3(3) . . . . ?
C21 C7 C8 C17 -0.8(4) . . . . ?
N4 C7 C8 C30 -2.1(4) . . . . ?
C21 C7 C8 C30 177.8(3) . . . . ?
C45 N6 C10 C28 178.6(3) . . . . ?
C45 N6 C10 C19 -2.7(4) . . . . ?
C17 C9 C14 C21 -0.5(4) . . . . ?
C34 C9 C14 C21 180.0(3) . . . . ?
C17 C9 C14 C33 179.2(3) . . . . ?
C34 C9 C14 C33 -0.3(4) . . . . ?
C55 N1 C15 C69 -178.1(4) . . . . ?
C55 N1 C15 C65 -0.1(6) . . . . ?
C62 N2 C16 C68 -178.7(4) . . . . ?
C62 N2 C16 C66 0.1(6) . . . . ?
C30 C8 C17 C9 -176.2(3) . . . . ?
C7 C8 C17 C9 2.4(4) . . . . ?
C34 C9 C17 C8 177.8(3) . . . . ?
C14 C9 C17 C8 -1.8(4) . . . . ?
N6 C10 C19 C35 -176.3(3) . . . . ?
C28 C10 C19 C35 2.3(4) . . . . ?
N6 C10 C19 C36 2.9(4) . . . . ?
C28 C10 C19 C36 -178.4(3) . . . . ?
C35 C12 C20 C28 0.9(4) . . . . ?
C38 C12 C20 C28 -178.5(3) . . . . ?
C35 C12 C20 C42 -179.1(3) . . . . ?
C38 C12 C20 C42 1.6(4) . . . . ?
N4 C7 C21 C14 178.5(3) . . . . ?
C8 C7 C21 C14 -1.4(4) . . . . ?
C33 C14 C21 C7 -177.7(3) . . . . ?
C9 C14 C21 C7 2.0(4) . . . . ?
C47 C22 C23 C26 -0.1(5) . . . . ?
C47 C22 C23 O1 179.6(3) . . . . ?
C29 C18 C25 C50 -1.9(4) . . . . ?
C46 C18 C25 C50 178.4(3) . . . . ?
C29 C18 C25 C63 178.4(3) . . . . ?
C46 C18 C25 C63 -1.4(4) . . . . ?
O1 C23 C26 C27 180.0(3) . . . . ?
C22 C23 C26 C27 -0.4(5) . . . . ?
C47 C24 C27 C48 178.4(3) . . . . ?
C56 C24 C27 C48 -1.3(4) . . . . ?
C47 C24 C27 C26 -1.5(4) . . . . ?
C56 C24 C27 C26 178.9(3) . . . . ?
C23 C26 C27 C48 -178.7(3) . . . . ?
C23 C26 C27 C24 1.2(5) . . . . ?
N6 C10 C28 C20 176.5(3) . . . . ?
C19 C10 C28 C20 -2.1(5) . . . . ?
C42 C20 C28 C10 -179.6(3) . . . . ?
C12 C20 C28 C10 0.5(5) . . . . ?
C25 C18 C29 C31 0.9(5) . . . . ?
C46 C18 C29 C31 -179.3(3) . . . . ?
C17 C8 C30 C37 177.4(3) . . . . ?
C7 C8 C30 C37 -1.2(4) . . . . ?
C18 C29 C31 O2 -179.5(3) . . . . ?
C18 C29 C31 C39 0.2(5) . . . . ?
C7 N4 C32 C37 -2.8(5) . . . . ?
C21 C14 C33 C40 -179.8(3) . . . . ?
C9 C14 C33 C40 0.5(4) . . . . ?
C17 C9 C34 C43 -179.1(3) . . . . ?
C14 C9 C34 C43 0.5(4) . . . . ?
C38 C12 C35 C19 178.7(3) . . . . ?
C20 C12 C35 C19 -0.7(5) . . . . ?
C10 C19 C35 C12 -0.9(4) . . . . ?
C36 C19 C35 C12 179.9(3) . . . . ?
C35 C19 C36 C53 178.4(3) . . . . ?
C10 C19 C36 C53 -0.8(4) . . . . ?
C8 C30 C37 C32 2.5(5) . . . . ?
N4 C32 C37 C30 -0.5(5) . . . . ?
C35 C12 C38 C49 179.9(3) . . . . ?
C20 C12 C38 C49 -0.7(5) . . . . ?
O2 C31 C39 C50 179.3(3) . . . . ?
C29 C31 C39 C50 -0.3(5) . . . . ?
C14 C33 C40 C43 -0.8(5) . . . . ?
C28 C20 C42 C54 178.7(3) . . . . ?
C12 C20 C42 C54 -1.3(5) . . . . ?
C9 C34 C43 C40 -0.8(5) . . . . ?
C33 C40 C43 C34 0.9(5) . . . . ?
C10 N6 C45 C53 0.5(5) . . . . ?
C29 C18 C46 C52 -179.0(3) . . . . ?
C25 C18 C46 C52 0.8(5) . . . . ?
C23 C22 C47 C24 -0.3(5) . . . . ?
C27 C24 C47 C22 1.1(5) . . . . ?
C56 C24 C47 C22 -179.3(3) . . . . ?
O3 C41 C48 C27 -179.8(3) . . . . ?
C59 C41 C48 C27 0.0(5) . . . . ?
C24 C27 C48 C41 1.0(5) . . . . ?
C26 C27 C48 C41 -179.1(3) . . . . ?
C12 C38 C49 C54 -0.5(5) . . . . ?
C31 C39 C50 C25 -0.7(5) . . . . ?
C63 C25 C50 C39 -178.4(3) . . . . ?
C18 C25 C50 C39 1.8(5) . . . . ?
C18 C46 C52 O4 -179.4(3) . . . . ?
C18 C46 C52 C57 0.4(5) . . . . ?
C19 C36 C53 C45 -1.3(5) . . . . ?
N6 C45 C53 C36 1.5(5) . . . . ?
C20 C42 C54 C49 0.2(5) . . . . ?
C38 C49 C54 C42 0.8(5) . . . . ?
C15 N1 C55 C72 -1.6(6) . . . . ?
C47 C24 C56 C59 -179.1(3) . . . . ?
C27 C24 C56 C59 0.5(5) . . . . ?
O4 C52 C57 C63 178.8(3) . . . . ?
C46 C52 C57 C63 -1.0(5) . . . . ?
C24 C56 C59 C41 0.5(5) . . . . ?
O3 C41 C59 C56 179.1(3) . . . . ?
C48 C41 C59 C56 -0.7(5) . . . . ?
C76 C51 C60 C68 2.2(7) . . . . ?
C70 C51 C60 C68 -179.5(5) . . . . ?
C76 C51 C60 C78 -179.7(6) . . . . ?
C70 C51 C60 C78 -1.4(7) . . . . ?
C16 N2 C62 C71 -1.9(6) . . . . ?
C52 C57 C63 C25 0.4(5) . . . . ?
C50 C25 C63 C57 -178.9(3) . . . . ?
C18 C25 C63 C57 0.8(5) . . . . ?
C75 C44 C64 C69 1.1(7) . . . . ?
C67 C44 C64 C69 -179.2(5) . . . . ?
C75 C44 C64 C80 179.8(6) . . . . ?
C67 C44 C64 C80 -0.5(7) . . . . ?
C69 C15 C65 C75 -0.5(8) . . . . ?
N1 C15 C65 C75 -178.6(5) . . . . ?
C69 C15 C65 C77 -179.7(6) . . . . ?
N1 C15 C65 C77 2.2(7) . . . . ?
C68 C16 C66 C76 0.0(8) . . . . ?
N2 C16 C66 C76 -178.9(5) . . . . ?
C68 C16 C66 C79 -179.2(6) . . . . ?
N2 C16 C66 C79 1.9(7) . . . . ?
C73 C58 C67 C44 -1.0(8) . . . . ?
C75 C44 C67 C58 -179.6(6) . . . . ?
C64 C44 C67 C58 0.8(8) . . . . ?
N2 C16 C68 C60 177.8(4) . . . . ?
C66 C16 C68 C60 -1.0(8) . . . . ?
C51 C60 C68 C16 -0.1(8) . . . . ?
C78 C60 C68 C16 -178.0(6) . . . . ?
N1 C15 C69 C64 177.4(4) . . . . ?
C65 C15 C69 C64 -0.6(8) . . . . ?
C44 C64 C69 C15 0.3(8) . . . . ?
C80 C64 C69 C15 -178.3(6) . . . . ?
C74 C61 C70 C51 -1.9(8) . . . . ?
C76 C51 C70 C61 -180.0(6) . . . . ?
C60 C51 C70 C61 1.9(8) . . . . ?
N2 C62 C71 C79 1.2(9) . . . . ?
N1 C55 C72 C77 0.9(9) . . . . ?
C67 C58 C73 C80 1.1(9) . . . . ?
C70 C61 C74 C78 1.5(9) . . . . ?
C64 C44 C75 C65 -2.4(10) . . . . ?
C67 C44 C75 C65 178.0(6) . . . . ?
C15 C65 C75 C44 2.1(10) . . . . ?
C77 C65 C75 C44 -178.8(7) . . . . ?
C60 C51 C76 C66 -3.5(10) . . . . ?
C70 C51 C76 C66 178.4(6) . . . . ?
C16 C66 C76 C51 2.4(10) . . . . ?
C79 C66 C76 C51 -178.6(7) . . . . ?
C55 C72 C77 C65 1.5(12) . . . . ?
C75 C65 C77 C72 177.9(8) . . . . ?
C15 C65 C77 C72 -3.0(11) . . . . ?
C61 C74 C78 C60 -1.2(12) . . . . ?
C51 C60 C78 C74 1.1(11) . . . . ?
C68 C60 C78 C74 179.1(7) . . . . ?
C62 C71 C79 C66 1.1(12) . . . . ?
C76 C66 C79 C71 178.3(8) . . . . ?
C16 C66 C79 C71 -2.6(11) . . . . ?
C58 C73 C80 C64 -1.0(12) . . . . ?
C44 C64 C80 C73 0.7(11) . . . . ?
C69 C64 C80 C73 179.3(7) . . . . ?
