#------------------------------------------------------------------------------
#$Date: 2026-06-04 13:59:10 +0200 (Thu 04 de Jun de 2026) $
#$Revision: 306205 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/20/7252075.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_7252075
loop_
_publ_author_name
'Barton, Benita'
'Adam, Muhammad-Ameen'
'Hosten, Eric C.'
_publ_section_title
;
 The host potential of
 N,N′-bis(9-(4-methoxyphenyl)-9H-xanthen-9-yl)ethane-1,2-diamine
 for xylene and ethylbenzene isomers, and its selectivity behaviour in
 mixed guest solutions
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3188
_journal_page_last               3199
_journal_paper_doi               10.1039/D6CE00160B
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C42 H36 N2 O4, C8 H10'
_chemical_formula_sum            'C50 H46 N2 O4'
_chemical_formula_weight         738.89
_chemical_name_systematic
;
N,N'-Bis(9-(4-methoxyphenyl)-9H-xanthen-9-yl)ethane-1,2-diamine
;
_chemical_temperature_decomposition 294.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2025/1
_audit_update_record
;
2026-02-10 deposited with the CCDC.	2026-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.528(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.206(3)
_cell_length_b                   10.4572(14)
_cell_length_c                   21.564(3)
_cell_measurement_reflns_used    7234
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      23.49
_cell_measurement_theta_min      2.54
_cell_volume                     3869.3(10)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service V6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Ortep-3 for Windows V2023.1 (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2025/1 (Sheldrick, 2015b) and ShelXle (Hübschle, 2011)'
_computing_structure_solution    'SHELXT-2019/3 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Bruker PHOTON II 7 CCD detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1826
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            64336
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        23.472
_diffrn_reflns_theta_max         23.472
_diffrn_reflns_theta_min         2.190
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             70
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7424
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.546
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0041(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2025/1 (Sheldrick 2025)'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.1486
_refine_ls_R_factor_gt           0.1031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0440P)²+11.9630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.1993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3882
_reflns_number_total             5663
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ce00160b2.cif
_cod_data_source_block           cq422
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7252075
_shelx_shelxl_version_number     2025/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.998
_exptl_absorpt_special_details
'Additional spherical absorption correction applied with mu*r =  0.20'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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 0.3269(2) 0.8308(3) 0.86755(17) 0.0372(9) Uani 1 1 d . . . . .
O2 O 0.1561(2) 0.6513(4) 0.43909(18) 0.0455(11) Uani 1 1 d . . . . .
O3 O 0.5131(2) 0.1907(3) 0.91975(16) 0.0384(10) Uani 1 1 d . . . . .
O4 O 0.60537(19) 0.9060(3) 0.54916(17) 0.0378(9) Uani 1 1 d . . . . .
N1 N 0.2929(2) 0.5749(4) 0.71651(16) 0.0219(9) Uani 1 1 d . . . . .
H1 H 0.273750 0.498787 0.710255 0.033 Uiso 1 1 d R U . . .
N2 N 0.3037(2) 0.7031(4) 0.59990(17) 0.0245(10) Uani 1 1 d . . . . .
H2 H 0.338764 0.648002 0.622689 0.037 Uiso 1 1 d R U . . .
C1 C 0.3246(3) 0.6029(4) 0.7867(2) 0.0209(11) Uani 1 1 d . . . . .
C2 C 0.2362(3) 0.6675(4) 0.6773(2) 0.0234(11) Uani 1 1 d . . . . .
H2A H 0.252012 0.754653 0.694506 0.028 Uiso 1 1 calc R U . . .
H2B H 0.184532 0.649375 0.681118 0.028 Uiso 1 1 calc R U . . .
C3 C 0.2306(3) 0.6614(5) 0.6064(2) 0.0253(11) Uani 1 1 d . . . . .
H3A H 0.219055 0.572700 0.589977 0.030 Uiso 1 1 calc R U . . .
H3B H 0.187655 0.717175 0.579775 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3069(3) 0.7186(5) 0.5333(2) 0.0235(11) Uani 1 1 d . . . . .
C5 C 0.5355(4) 0.1781(6) 0.9883(3) 0.0578(18) Uani 1 1 d . . . . .
H5A H 0.567871 0.101534 1.002258 0.087 Uiso 1 1 calc R U . . .
H5B H 0.488977 0.170412 1.001228 0.087 Uiso 1 1 calc R U . . .
H5C H 0.565382 0.253673 1.009333 0.087 Uiso 1 1 calc R U . . .
C6 C 0.6565(3) 0.9568(6) 0.6086(3) 0.0513(17) Uani 1 1 d . . . . .
H6A H 0.631165 1.028459 0.622739 0.077 Uiso 1 1 calc R U . . .
H6B H 0.704214 0.987030 0.601818 0.077 Uiso 1 1 calc R U . . .
H6C H 0.669668 0.890308 0.642586 0.077 Uiso 1 1 calc R U . . .
C11 C 0.26083(15) 0.6378(3) 0.81611(14) 0.0215(11) Uani 1 1 d G . . . .
C12 C 0.26788(15) 0.7471(3) 0.85436(15) 0.0266(12) Uani 1 1 d G . . . .
C13 C 0.21004(19) 0.7779(3) 0.88064(15) 0.0373(14) Uani 1 1 d G . . . .
H13 H 0.214862 0.852543 0.906783 0.045 Uiso 1 1 calc R U . . .
C14 C 0.14516(17) 0.6993(3) 0.86867(16) 0.0405(14) Uani 1 1 d G . . . .
H14 H 0.105639 0.720374 0.886629 0.049 Uiso 1 1 calc R U . . .
C15 C 0.13811(15) 0.5901(3) 0.83042(16) 0.0379(14) Uani 1 1 d G . . . .
H15 H 0.093771 0.536397 0.822237 0.045 Uiso 1 1 calc R U . . .
C16 C 0.19594(17) 0.5593(2) 0.80414(14) 0.0294(12) Uani 1 1 d G . . . .
H16 H 0.191126 0.484586 0.777997 0.035 Uiso 1 1 calc R U . . .
C21 C 0.38100(16) 0.7154(3) 0.79586(15) 0.0247(12) Uani 1 1 d G . . . .
C22 C 0.37908(17) 0.8178(3) 0.83637(14) 0.0298(12) Uani 1 1 d G . . . .
C23 C 0.4328(2) 0.9166(2) 0.84575(15) 0.0387(14) Uani 1 1 d G . . . .
H23 H 0.431478 0.986627 0.873433 0.046 Uiso 1 1 calc R U . . .
C24 C 0.48840(17) 0.9130(3) 0.81461(17) 0.0437(16) Uani 1 1 d G . . . .
H24 H 0.525108 0.980507 0.821017 0.052 Uiso 1 1 calc R U . . .
C25 C 0.49032(16) 0.8105(3) 0.77410(16) 0.0407(14) Uani 1 1 d G . . . .
H25 H 0.528330 0.808066 0.752818 0.049 Uiso 1 1 calc R U . . .
C26 C 0.43661(18) 0.7118(3) 0.76472(14) 0.0336(13) Uani 1 1 d G . . . .
H26 H 0.437922 0.641743 0.737036 0.040 Uiso 1 1 calc R U . . .
C31 C 0.37173(16) 0.4877(2) 0.82271(12) 0.0212(11) Uani 1 1 d G . . . .
C32 C 0.38974(17) 0.4781(2) 0.89047(12) 0.0260(12) Uani 1 1 d G . . . .
H32 H 0.369756 0.539194 0.913302 0.031 Uiso 1 1 calc R U . . .
C33 C 0.43698(18) 0.3792(3) 0.92481(9) 0.0257(12) Uani 1 1 d G . . . .
H33 H 0.449281 0.372688 0.971118 0.031 Uiso 1 1 calc R U . . .
C34 C 0.46621(16) 0.2899(2) 0.89140(13) 0.0254(12) Uani 1 1 d G . . . .
C35 C 0.44821(17) 0.2994(2) 0.82364(13) 0.0293(12) Uani 1 1 d G . . . .
H35 H 0.468191 0.238320 0.800803 0.035 Uiso 1 1 calc R U . . .
C36 C 0.40097(18) 0.3983(3) 0.78929(9) 0.0277(12) Uani 1 1 d G . . . .
H36 H 0.388667 0.404825 0.742986 0.033 Uiso 1 1 calc R U . . .
C41 C 0.24482(15) 0.8152(2) 0.49825(14) 0.0232(11) Uani 1 1 d G . . . .
C42 C 0.17439(17) 0.7741(2) 0.45353(15) 0.0340(13) Uani 1 1 d G . . . .
C43 C 0.11673(14) 0.8625(3) 0.42273(14) 0.0436(15) Uani 1 1 d G . . . .
H43 H 0.068596 0.834423 0.392160 0.052 Uiso 1 1 calc R U . . .
C44 C 0.12948(18) 0.9921(3) 0.43665(16) 0.0445(16) Uani 1 1 d G . . . .
H44 H 0.090063 1.052477 0.415597 0.053 Uiso 1 1 calc R U . . .
C45 C 0.1999(2) 1.0332(2) 0.48137(17) 0.0421(15) Uani 1 1 d G . . . .
H45 H 0.208613 1.121693 0.490889 0.051 Uiso 1 1 calc R U . . .
C46 C 0.25757(15) 0.9448(3) 0.51218(14) 0.0321(13) Uani 1 1 d G . . . .
H46 H 0.305697 0.972856 0.542744 0.038 Uiso 1 1 calc R U . . .
C51 C 0.29001(17) 0.5920(2) 0.49554(14) 0.0255(12) Uani 1 1 d G . . . .
C52 C 0.21464(15) 0.5661(3) 0.45424(16) 0.0320(13) Uani 1 1 d G . . . .
C53 C 0.19692(15) 0.4475(3) 0.42379(16) 0.0433(15) Uani 1 1 d G . . . .
H53 H 0.145417 0.429798 0.395561 0.052 Uiso 1 1 calc R U . . .
C54 C 0.2546(2) 0.3548(2) 0.43464(16) 0.0425(15) Uani 1 1 d G . . . .
H54 H 0.242458 0.273706 0.413827 0.051 Uiso 1 1 calc R U . . .
C55 C 0.32993(18) 0.3807(3) 0.47594(17) 0.0371(14) Uani 1 1 d G . . . .
H55 H 0.369328 0.317294 0.483352 0.045 Uiso 1 1 calc R U . . .
C56 C 0.34765(14) 0.4993(3) 0.50639(15) 0.0326(13) Uani 1 1 d G . . . .
H56 H 0.399158 0.516973 0.534613 0.039 Uiso 1 1 calc R U . . .
C61 C 0.38825(13) 0.7689(3) 0.53946(13) 0.0239(11) Uani 1 1 d G . . . .
C62 C 0.43681(16) 0.8186(3) 0.59879(11) 0.0298(12) Uani 1 1 d G . . . .
H62 H 0.420113 0.820088 0.636076 0.036 Uiso 1 1 calc R U . . .
C63 C 0.50979(15) 0.8662(3) 0.60356(12) 0.0318(13) Uani 1 1 d G . . . .
H63 H 0.542976 0.900157 0.644106 0.038 Uiso 1 1 calc R U . . .
C64 C 0.53422(13) 0.8641(3) 0.54900(15) 0.0293(12) Uani 1 1 d G . . . .
C65 C 0.48566(17) 0.8144(3) 0.48968(12) 0.0317(13) Uani 1 1 d G . . . .
H65 H 0.502359 0.812908 0.452390 0.038 Uiso 1 1 calc R U . . .
C66 C 0.41268(16) 0.7668(3) 0.48491(11) 0.0297(12) Uani 1 1 d G . . . .
H66 H 0.379495 0.732838 0.444359 0.036 Uiso 1 1 calc R U . . .
C71 C 0.2793(2) 0.7205(5) 0.2874(2) 0.0557(18) Uani 1 1 d G . . . .
C72 C 0.3219(2) 0.6169(4) 0.32132(19) 0.0530(17) Uani 1 1 d G . . . .
H72 H 0.300498 0.562627 0.346200 0.064 Uiso 1 1 calc R U . . .
C73 C 0.3960(2) 0.5928(5) 0.3189(2) 0.068(2) Uani 1 1 d G . . . .
C74 C 0.4274(2) 0.6722(7) 0.2825(3) 0.138(5) Uani 1 1 d G . . . .
H74 H 0.477968 0.655742 0.280764 0.165 Uiso 1 1 calc R U . . .
C75 C 0.3847(3) 0.7758(6) 0.2485(3) 0.163(6) Uani 1 1 d G . . . .
H75 H 0.406120 0.830108 0.223651 0.196 Uiso 1 1 calc R U . . .
C76 C 0.3106(3) 0.7999(5) 0.2510(3) 0.100(3) Uani 1 1 d G . . . .
H76 H 0.281460 0.870735 0.227812 0.120 Uiso 1 1 calc R U . . .
C77 C 0.2007(4) 0.7501(11) 0.2905(4) 0.114(4) Uani 1 1 d . . . . .
H77A H 0.164986 0.769062 0.246150 0.171 Uiso 1 1 calc R U . . .
H77B H 0.204093 0.824387 0.318988 0.171 Uiso 1 1 calc R U . . .
H77C H 0.181240 0.676272 0.308318 0.171 Uiso 1 1 calc R U . . .
C78 C 0.4417(5) 0.4814(9) 0.3562(4) 0.111(3) Uani 1 1 d . . . . .
H78A H 0.487600 0.467404 0.343011 0.167 Uiso 1 1 calc R U . . .
H78B H 0.408950 0.404597 0.346570 0.167 Uiso 1 1 calc R U . . .
H78C H 0.458381 0.499363 0.403516 0.167 Uiso 1 1 calc R U . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 0.00 3.00 0.0110
-1.00 0.00 -3.00 0.0280
-1.00 -4.00 1.00 0.2330
1.00 0.00 3.00 0.0350
1.00 4.00 -1.00 0.2460
4.00 0.00 -3.00 0.0090
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
C12 O1 C22 118.6(3) . . ?
C42 O2 C52 117.7(3) . . ?
C34 O3 C5 117.7(4) . . ?
C64 O4 C6 117.4(4) . . ?
C1 N1 C2 115.2(3) . . ?
C1 N1 H1 110.3 . . ?
C2 N1 H1 110.5 . . ?
C3 N2 C4 117.8(3) . . ?
C3 N2 H2 105.5 . . ?
C4 N2 H2 111.1 . . ?
N1 C1 C21 107.7(3) . . ?
N1 C1 C31 109.1(3) . . ?
C21 C1 C31 107.6(3) . . ?
N1 C1 C11 112.6(3) . . ?
C21 C1 C11 109.3(3) . . ?
C31 C1 C11 110.5(3) . . ?
N1 C2 C3 110.9(4) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 C2 109.5(4) . . ?
N2 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
N2 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C41 107.1(3) . . ?
N2 C4 C51 111.0(4) . . ?
C41 C4 C51 109.1(3) . . ?
N2 C4 C61 107.9(3) . . ?
C41 C4 C61 110.6(3) . . ?
C51 C4 C61 111.0(3) . . ?
O3 C5 H5A 109.5 . . ?
O3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C11 C16 120.0 . . ?
C12 C11 C1 120.4(2) . . ?
C16 C11 C1 119.6(2) . . ?
O1 C12 C11 124.8(3) . . ?
O1 C12 C13 115.1(3) . . ?
C11 C12 C13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.0 . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C21 C26 120.0 . . ?
C22 C21 C1 121.1(3) . . ?
C26 C21 C1 118.9(3) . . ?
O1 C22 C21 124.3(3) . . ?
O1 C22 C23 115.7(3) . . ?
C21 C22 C23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C1 119.0(2) . . ?
C36 C31 C1 120.9(2) . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
O3 C34 C33 125.1(2) . . ?
O3 C34 C35 114.9(2) . . ?
C33 C34 C35 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C42 C41 C46 120.0 . . ?
C42 C41 C4 120.1(3) . . ?
C46 C41 C4 119.9(3) . . ?
O2 C42 C43 116.0(2) . . ?
O2 C42 C41 124.0(2) . . ?
C43 C42 C41 120.0 . . ?
C42 C43 C44 120.0 . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C45 C44 C43 120.0 . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.0 . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 120.0 . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?
C52 C51 C56 120.0 . . ?
C52 C51 C4 119.3(2) . . ?
C56 C51 C4 120.5(2) . . ?
O2 C52 C51 124.1(3) . . ?
O2 C52 C53 115.9(3) . . ?
C51 C52 C53 120.0 . . ?
C52 C53 C54 120.0 . . ?
C52 C53 H53 120.0 . . ?
C54 C53 H53 120.0 . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C56 C55 C54 120.0 . . ?
C56 C55 H55 120.0 . . ?
C54 C55 H55 120.0 . . ?
C55 C56 C51 120.0 . . ?
C55 C56 H56 120.0 . . ?
C51 C56 H56 120.0 . . ?
C62 C61 C66 120.0 . . ?
C62 C61 C4 120.4(2) . . ?
C66 C61 C4 119.6(2) . . ?
C61 C62 C63 120.0 . . ?
C61 C62 H62 120.0 . . ?
C63 C62 H62 120.0 . . ?
C64 C63 C62 120.0 . . ?
C64 C63 H63 120.0 . . ?
C62 C63 H63 120.0 . . ?
O4 C64 C65 115.7(2) . . ?
O4 C64 C63 124.3(2) . . ?
C65 C64 C63 120.0 . . ?
C64 C65 C66 120.0 . . ?
C64 C65 H65 120.0 . . ?
C66 C65 H65 120.0 . . ?
C65 C66 C61 120.0 . . ?
C65 C66 H66 120.0 . . ?
C61 C66 H66 120.0 . . ?
C72 C71 C76 120.0 . . ?
C72 C71 C77 121.0(5) . . ?
C76 C71 C77 118.9(5) . . ?
C71 C72 C73 120.0 . . ?
C71 C72 H72 120.0 . . ?
C73 C72 H72 120.0 . . ?
C74 C73 C72 120.0 . . ?
C74 C73 C78 120.6(5) . . ?
C72 C73 C78 119.4(5) . . ?
C73 C74 C75 120.0 . . ?
C73 C74 H74 120.0 . . ?
C75 C74 H74 120.0 . . ?
C74 C75 C76 120.0 . . ?
C74 C75 H75 120.0 . . ?
C76 C75 H75 120.0 . . ?
C75 C76 C71 120.0 . . ?
C75 C76 H76 120.0 . . ?
C71 C76 H76 120.0 . . ?
C71 C77 H77A 109.5 . . ?
C71 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
C71 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
C73 C78 H78A 109.5 . . ?
C73 C78 H78B 109.5 . . ?
H78A C78 H78B 109.5 . . ?
C73 C78 H78C 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
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 C12 1.341(4) . ?
O1 C22 1.341(4) . ?
O2 C42 1.337(4) . ?
O2 C52 1.343(4) . ?
O3 C34 1.353(4) . ?
O3 C5 1.402(6) . ?
O4 C64 1.367(4) . ?
O4 C6 1.413(6) . ?
N1 C1 1.459(5) . ?
N1 C2 1.461(5) . ?
N1 H1 0.8614 . ?
N2 C3 1.451(6) . ?
N2 C4 1.465(6) . ?
N2 H2 0.8787 . ?
C1 C21 1.530(5) . ?
C1 C31 1.531(5) . ?
C1 C11 1.541(5) . ?
C2 C3 1.499(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C41 1.516(5) . ?
C4 C51 1.531(5) . ?
C4 C61 1.535(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C22 C23 1.3900 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C26 1.3900 . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C32 C33 1.3900 . ?
C32 H32 0.9500 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 C35 1.3900 . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.3900 . ?
C41 C46 1.3900 . ?
C42 C43 1.3900 . ?
C43 C44 1.3900 . ?
C43 H43 0.9500 . ?
C44 C45 1.3900 . ?
C44 H44 0.9500 . ?
C45 C46 1.3900 . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C52 C53 1.3900 . ?
C53 C54 1.3900 . ?
C53 H53 0.9500 . ?
C54 C55 1.3900 . ?
C54 H54 0.9500 . ?
C55 C56 1.3900 . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C62 1.3900 . ?
C61 C66 1.3900 . ?
C62 C63 1.3900 . ?
C62 H62 0.9500 . ?
C63 C64 1.3900 . ?
C63 H63 0.9500 . ?
C64 C65 1.3900 . ?
C65 C66 1.3900 . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C71 C72 1.3900 . ?
C71 C76 1.3900 . ?
C71 C77 1.486(8) . ?
C72 C73 1.3900 . ?
C72 H72 0.9500 . ?
C73 C74 1.3900 . ?
C73 C78 1.500(9) . ?
C74 C75 1.3900 . ?
C74 H74 0.9500 . ?
C75 C76 1.3900 . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
C77 H77A 0.9800 . ?
C77 H77B 0.9800 . ?
C77 H77C 0.9800 . ?
C78 H78A 0.9800 . ?
C78 H78B 0.9800 . ?
C78 H78C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 N1 0.88 2.55 2.913(5) 106 . yes
C36 H36 N1 0.95 2.42 2.771(4) 102 . yes
C55 H55 O4 0.95 2.52 3.331(4) 143 3_666 yes
C62 H62 N2 0.95 2.34 2.716(5) 103 . yes
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
C2 N1 C1 C21 -73.2(4) . . . . ?
C2 N1 C1 C31 170.4(3) . . . . ?
C2 N1 C1 C11 47.4(5) . . . . ?
C1 N1 C2 C3 158.1(4) . . . . ?
C4 N2 C3 C2 -172.9(4) . . . . ?
N1 C2 C3 N2 -66.1(5) . . . . ?
C3 N2 C4 C41 58.3(5) . . . . ?
C3 N2 C4 C51 -60.7(5) . . . . ?
C3 N2 C4 C61 177.4(4) . . . . ?
N1 C1 C11 C12 -130.1(3) . . . . ?
C21 C1 C11 C12 -10.5(4) . . . . ?
C31 C1 C11 C12 107.6(3) . . . . ?
N1 C1 C11 C16 49.9(4) . . . . ?
C21 C1 C11 C16 169.4(2) . . . . ?
C31 C1 C11 C16 -72.4(3) . . . . ?
C22 O1 C12 C11 7.7(5) . . . . ?
C22 O1 C12 C13 -170.6(3) . . . . ?
C16 C11 C12 O1 -178.2(3) . . . . ?
C1 C11 C12 O1 1.7(4) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C1 C11 C12 C13 180.0(3) . . . . ?
O1 C12 C13 C14 178.4(3) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C1 C11 C16 C15 -180.0(3) . . . . ?
N1 C1 C21 C22 134.0(3) . . . . ?
C31 C1 C21 C22 -108.6(3) . . . . ?
C11 C1 C21 C22 11.4(4) . . . . ?
N1 C1 C21 C26 -48.4(4) . . . . ?
C31 C1 C21 C26 69.1(3) . . . . ?
C11 C1 C21 C26 -170.9(2) . . . . ?
C12 O1 C22 C21 -6.8(5) . . . . ?
C12 O1 C22 C23 172.1(3) . . . . ?
C26 C21 C22 O1 178.8(3) . . . . ?
C1 C21 C22 O1 -3.5(4) . . . . ?
C26 C21 C22 C23 0.0 . . . . ?
C1 C21 C22 C23 177.6(3) . . . . ?
O1 C22 C23 C24 -178.9(3) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C21 0.0 . . . . ?
C22 C21 C26 C25 0.0 . . . . ?
C1 C21 C26 C25 -177.7(3) . . . . ?
N1 C1 C31 C32 -163.0(3) . . . . ?
C21 C1 C31 C32 80.4(3) . . . . ?
C11 C1 C31 C32 -38.8(4) . . . . ?
N1 C1 C31 C36 21.5(4) . . . . ?
C21 C1 C31 C36 -95.0(3) . . . . ?
C11 C1 C31 C36 145.7(2) . . . . ?
C36 C31 C32 C33 0.0 . . . . ?
C1 C31 C32 C33 -175.5(3) . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C5 O3 C34 C33 -1.4(5) . . . . ?
C5 O3 C34 C35 178.0(4) . . . . ?
C32 C33 C34 O3 179.4(3) . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
O3 C34 C35 C36 -179.4(3) . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C31 0.0 . . . . ?
C32 C31 C36 C35 0.0 . . . . ?
C1 C31 C36 C35 175.4(3) . . . . ?
N2 C4 C41 C42 -101.7(3) . . . . ?
C51 C4 C41 C42 18.6(4) . . . . ?
C61 C4 C41 C42 140.9(3) . . . . ?
N2 C4 C41 C46 76.6(4) . . . . ?
C51 C4 C41 C46 -163.1(3) . . . . ?
C61 C4 C41 C46 -40.8(4) . . . . ?
C52 O2 C42 C43 164.0(3) . . . . ?
C52 O2 C42 C41 -18.5(5) . . . . ?
C46 C41 C42 O2 -177.4(4) . . . . ?
C4 C41 C42 O2 0.9(4) . . . . ?
C46 C41 C42 C43 0.0 . . . . ?
C4 C41 C42 C43 178.3(3) . . . . ?
O2 C42 C43 C44 177.6(4) . . . . ?
C41 C42 C43 C44 0.0 . . . . ?
C42 C43 C44 C45 0.0 . . . . ?
C43 C44 C45 C46 0.0 . . . . ?
C44 C45 C46 C41 0.0 . . . . ?
C42 C41 C46 C45 0.0 . . . . ?
C4 C41 C46 C45 -178.3(3) . . . . ?
N2 C4 C51 C52 95.3(3) . . . . ?
C41 C4 C51 C52 -22.5(4) . . . . ?
C61 C4 C51 C52 -144.6(3) . . . . ?
N2 C4 C51 C56 -79.4(4) . . . . ?
C41 C4 C51 C56 162.8(2) . . . . ?
C61 C4 C51 C56 40.7(4) . . . . ?
C42 O2 C52 C51 13.9(5) . . . . ?
C42 O2 C52 C53 -163.7(3) . . . . ?
C56 C51 C52 O2 -177.5(4) . . . . ?
C4 C51 C52 O2 7.8(4) . . . . ?
C56 C51 C52 C53 0.0 . . . . ?
C4 C51 C52 C53 -174.7(3) . . . . ?
O2 C52 C53 C54 177.7(3) . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C51 0.0 . . . . ?
C52 C51 C56 C55 0.0 . . . . ?
C4 C51 C56 C55 174.7(3) . . . . ?
N2 C4 C61 C62 -14.7(4) . . . . ?
C41 C4 C61 C62 102.2(3) . . . . ?
C51 C4 C61 C62 -136.6(3) . . . . ?
N2 C4 C61 C66 166.5(3) . . . . ?
C41 C4 C61 C66 -76.6(4) . . . . ?
C51 C4 C61 C66 44.7(4) . . . . ?
C66 C61 C62 C63 0.0 . . . . ?
C4 C61 C62 C63 -178.8(3) . . . . ?
C61 C62 C63 C64 0.0 . . . . ?
C6 O4 C64 C65 -179.8(4) . . . . ?
C6 O4 C64 C63 -1.2(5) . . . . ?
C62 C63 C64 O4 -178.6(3) . . . . ?
C62 C63 C64 C65 0.0 . . . . ?
O4 C64 C65 C66 178.7(3) . . . . ?
C63 C64 C65 C66 0.0 . . . . ?
C64 C65 C66 C61 0.0 . . . . ?
C62 C61 C66 C65 0.0 . . . . ?
C4 C61 C66 C65 178.8(3) . . . . ?
C76 C71 C72 C73 0.0 . . . . ?
C77 C71 C72 C73 -178.6(6) . . . . ?
C71 C72 C73 C74 0.0 . . . . ?
C71 C72 C73 C78 179.4(6) . . . . ?
C72 C73 C74 C75 0.0 . . . . ?
C78 C73 C74 C75 -179.4(6) . . . . ?
C73 C74 C75 C76 0.0 . . . . ?
C74 C75 C76 C71 0.0 . . . . ?
C72 C71 C76 C75 0.0 . . . . ?
C77 C71 C76 C75 178.6(6) . . . . ?
