#------------------------------------------------------------------------------
#$Date: 2026-06-04 13:59:10 +0200 (Thu 04 de Jun de 2026) $
#$Revision: 306205 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/20/7252074.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_7252074
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 314.85
_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                 111.015(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8696(12)
_cell_length_b                   10.5775(7)
_cell_length_c                   22.5364(14)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.30
_cell_volume                     3976.4(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.986
_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  0.1057
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            137242
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.451
_diffrn_reflns_theta_min         2.155
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             70
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0019(4)
_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   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         8078
_refine_ls_number_restraints     222
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0760
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0225P)²+4.2166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6436
_reflns_number_total             8078
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ce00160b2.cif
_cod_data_source_block           cq395
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7252074
_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   0.962
_shelx_estimated_absorpt_t_max   0.997
_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 0.15865(10) 0.63879(17) 0.45244(9) 0.0411(5) Uani 1 1 d . . . . .
O2 O 0.61614(10) 0.91228(18) 0.55714(9) 0.0430(5) Uani 1 1 d . . . . .
O3 O 0.32866(10) 0.83071(16) 0.86329(8) 0.0382(4) Uani 1 1 d . . . . .
O4 O 0.51440(10) 0.18281(16) 0.92560(8) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.31061(11) 0.70160(18) 0.60917(8) 0.0263(4) Uani 1 1 d . . . . .
H1 H 0.347453 0.646670 0.630852 0.039 Uiso 1 1 d R U . . .
N2 N 0.29777(10) 0.57053(18) 0.72041(8) 0.0236(4) Uani 1 1 d . . . . .
H2 H 0.278084 0.500053 0.714712 0.035 Uiso 1 1 d R U . . .
C1 C 0.31393(13) 0.7142(2) 0.54465(10) 0.0243(5) Uani 1 1 d . . . . .
C2 C 0.23471(13) 0.6586(2) 0.61283(10) 0.0256(5) Uani 1 1 d . . . . .
H2A H 0.223479 0.571073 0.596484 0.031 Uiso 1 1 calc R U . . .
H2B H 0.190529 0.713561 0.586313 0.031 Uiso 1 1 calc R U . . .
C3 C 0.23963(13) 0.6631(2) 0.68112(10) 0.0265(5) Uani 1 1 d . . . . .
H3A H 0.255752 0.749069 0.698380 0.032 Uiso 1 1 calc R U . . .
H3B H 0.186118 0.645199 0.682935 0.032 Uiso 1 1 calc R U . . .
C4 C 0.32937(13) 0.6002(2) 0.78895(10) 0.0238(5) Uani 1 1 d . . . . .
C5 C 0.66972(17) 0.9685(3) 0.61376(15) 0.0557(8) Uani 1 1 d . . . . .
H5A H 0.715812 1.003958 0.605660 0.083 Uiso 1 1 calc R U . . .
H5B H 0.688288 0.904222 0.647192 0.083 Uiso 1 1 calc R U . . .
H5C H 0.641986 1.035988 0.627452 0.083 Uiso 1 1 calc R U . . .
C6 C 0.5368(2) 0.1737(3) 0.99282(13) 0.0550(8) Uani 1 1 d . . . . .
H6A H 0.488616 0.165521 1.003647 0.082 Uiso 1 1 calc R U . . .
H6B H 0.566302 0.249928 1.012827 0.082 Uiso 1 1 calc R U . . .
H6C H 0.571049 0.099347 1.008244 0.082 Uiso 1 1 calc R U . . .
C11 C 0.24867(13) 0.8077(2) 0.50735(10) 0.0247(5) Uani 1 1 d . . . . .
C12 C 0.17620(14) 0.7660(2) 0.46415(11) 0.0304(5) Uani 1 1 d . . . . .
C13 C 0.11582(16) 0.8489(3) 0.43066(12) 0.0415(7) Uani 1 1 d . . . . .
H13 H 0.066879 0.818006 0.400789 0.050 Uiso 1 1 calc R U . . .
C14 C 0.12773(17) 0.9764(3) 0.44127(13) 0.0462(7) Uani 1 1 d . . . . .
H14 H 0.087072 1.034306 0.418171 0.055 Uiso 1 1 calc R U . . .
C15 C 0.19856(17) 1.0210(3) 0.48537(13) 0.0425(7) Uani 1 1 d . . . . .
H15 H 0.205961 1.109164 0.493381 0.051 Uiso 1 1 calc R U . . .
C16 C 0.25851(15) 0.9372(2) 0.51775(12) 0.0330(6) Uani 1 1 d . . . . .
H16 H 0.307303 0.968592 0.547636 0.040 Uiso 1 1 calc R U . . .
C21 C 0.29812(14) 0.5879(2) 0.50952(11) 0.0269(5) Uani 1 1 d . . . . .
C22 C 0.22194(14) 0.5549(2) 0.46875(11) 0.0322(6) Uani 1 1 d . . . . .
C23 C 0.20440(18) 0.4356(3) 0.44122(13) 0.0416(6) Uani 1 1 d . . . . .
H23 H 0.151130 0.414590 0.414890 0.050 Uiso 1 1 calc R U . . .
C24 C 0.2649(2) 0.3487(3) 0.45255(14) 0.0482(7) Uani 1 1 d . . . . .
H24 H 0.253835 0.267488 0.433418 0.058 Uiso 1 1 calc R U . . .
C25 C 0.34194(19) 0.3792(3) 0.49171(14) 0.0466(7) Uani 1 1 d . . . . .
H25 H 0.383862 0.319186 0.499098 0.056 Uiso 1 1 calc R U . . .
C26 C 0.35817(16) 0.4966(2) 0.52014(12) 0.0367(6) Uani 1 1 d . . . . .
H26 H 0.411268 0.515792 0.547520 0.044 Uiso 1 1 calc R U . . .
C31 C 0.39636(13) 0.7662(2) 0.55083(11) 0.0265(5) Uani 1 1 d . . . . .
C32 C 0.45125(14) 0.8081(2) 0.60784(11) 0.0339(6) Uani 1 1 d . . . . .
H32 H 0.438189 0.803096 0.645089 0.041 Uiso 1 1 calc R U . . .
C33 C 0.52532(15) 0.8576(3) 0.61220(12) 0.0380(6) Uani 1 1 d . . . . .
H33 H 0.562220 0.884977 0.652114 0.046 Uiso 1 1 calc R U . . .
C34 C 0.54500(14) 0.8668(2) 0.55860(12) 0.0327(6) Uani 1 1 d . . . . .
C35 C 0.49001(15) 0.8269(2) 0.50061(12) 0.0347(6) Uani 1 1 d . . . . .
H35 H 0.502616 0.834015 0.463221 0.042 Uiso 1 1 calc R U . . .
C36 C 0.41737(14) 0.7770(2) 0.49705(11) 0.0322(6) Uani 1 1 d . . . . .
H36 H 0.380701 0.749402 0.457094 0.039 Uiso 1 1 calc R U . . .
C41 C 0.26347(13) 0.6355(2) 0.81460(10) 0.0242(5) Uani 1 1 d . . . . .
C42 C 0.26668(14) 0.7444(2) 0.84951(10) 0.0279(5) Uani 1 1 d . . . . .
C43 C 0.20758(16) 0.7744(2) 0.87385(12) 0.0375(6) Uani 1 1 d . . . . .
H43 H 0.211962 0.848878 0.898413 0.045 Uiso 1 1 calc R U . . .
C44 C 0.14285(16) 0.6955(3) 0.86213(12) 0.0405(6) Uani 1 1 d . . . . .
H44 H 0.102202 0.715450 0.878570 0.049 Uiso 1 1 calc R U . . .
C45 C 0.13677(15) 0.5872(3) 0.82643(12) 0.0393(6) Uani 1 1 d . . . . .
H45 H 0.091494 0.533439 0.817592 0.047 Uiso 1 1 calc R U . . .
C46 C 0.19683(14) 0.5575(2) 0.80362(11) 0.0317(5) Uani 1 1 d . . . . .
H46 H 0.192648 0.481915 0.779849 0.038 Uiso 1 1 calc R U . . .
C51 C 0.38720(13) 0.7113(2) 0.79889(10) 0.0260(5) Uani 1 1 d . . . . .
C52 C 0.38493(14) 0.8159(2) 0.83484(11) 0.0303(5) Uani 1 1 d . . . . .
C53 C 0.43946(16) 0.9148(2) 0.84489(12) 0.0398(6) Uani 1 1 d . . . . .
H53 H 0.437046 0.985029 0.870440 0.048 Uiso 1 1 calc R U . . .
C54 C 0.49690(16) 0.9100(3) 0.81746(13) 0.0457(7) Uani 1 1 d . . . . .
H54 H 0.534129 0.977349 0.823827 0.055 Uiso 1 1 calc R U . . .
C55 C 0.50052(15) 0.8074(3) 0.78069(12) 0.0428(7) Uani 1 1 d . . . . .
H55 H 0.539993 0.804301 0.761560 0.051 Uiso 1 1 calc R U . . .
C56 C 0.44645(14) 0.7090(3) 0.77178(11) 0.0342(6) Uani 1 1 d . . . . .
H56 H 0.449643 0.638362 0.746741 0.041 Uiso 1 1 calc R U . . .
C61 C 0.37666(12) 0.4853(2) 0.82561(10) 0.0236(5) Uani 1 1 d . . . . .
C62 C 0.40653(13) 0.3927(2) 0.79640(11) 0.0278(5) Uani 1 1 d . . . . .
H62 H 0.395819 0.397751 0.752016 0.033 Uiso 1 1 calc R U . . .
C63 C 0.45173(13) 0.2930(2) 0.83105(11) 0.0296(5) Uani 1 1 d . . . . .
H63 H 0.471061 0.229986 0.810164 0.036 Uiso 1 1 calc R U . . .
C64 C 0.46888(13) 0.2848(2) 0.89589(11) 0.0267(5) Uani 1 1 d . . . . .
C65 C 0.43979(13) 0.3761(2) 0.92590(11) 0.0283(5) Uani 1 1 d . . . . .
H65 H 0.451102 0.371263 0.970364 0.034 Uiso 1 1 calc R U . . .
C66 C 0.39410(13) 0.4747(2) 0.89076(11) 0.0270(5) Uani 1 1 d . . . . .
H66 H 0.374108 0.536799 0.911697 0.032 Uiso 1 1 calc R U . . .
C71 C 0.3511(2) 0.6296(4) 0.3117(2) 0.0727(17) Uani 0.665(5) 1 d DG U P A 1
C72 C 0.3405(2) 0.7247(5) 0.2668(2) 0.080(2) Uani 0.665(5) 1 d DG U P A 1
C73 C 0.2726(3) 0.8008(4) 0.24957(19) 0.089(2) Uani 0.665(5) 1 d DG U P A 1
H73 H 0.265381 0.865781 0.218898 0.106 Uiso 0.665(5) 1 calc R U P A 1
C74 C 0.2154(2) 0.7819(4) 0.2772(2) 0.081(2) Uani 0.665(5) 1 d DG U P A 1
H74 H 0.168967 0.833903 0.265403 0.097 Uiso 0.665(5) 1 calc R U P A 1
C75 C 0.2259(2) 0.6868(4) 0.3221(2) 0.0636(17) Uani 0.665(5) 1 d DG U P A 1
H75 H 0.186806 0.673884 0.340944 0.076 Uiso 0.665(5) 1 calc R U P A 1
C76 C 0.2938(2) 0.6107(4) 0.33931(17) 0.0625(14) Uani 0.665(5) 1 d DG U P A 1
H76 H 0.301059 0.545741 0.369981 0.075 Uiso 0.665(5) 1 calc R U P A 1
C77 C 0.4248(6) 0.5465(11) 0.3331(6) 0.147(4) Uani 0.665(5) 1 d D U P A 1
H77A H 0.420961 0.485760 0.364743 0.220 Uiso 0.665(5) 1 calc R U P A 1
H77B H 0.428619 0.500807 0.296489 0.220 Uiso 0.665(5) 1 calc R U P A 1
H77C H 0.472660 0.599069 0.352058 0.220 Uiso 0.665(5) 1 calc R U P A 1
C78 C 0.3980(6) 0.7445(12) 0.2318(5) 0.171(4) Uani 0.665(5) 1 d D U P A 1
H78A H 0.443005 0.685479 0.248280 0.257 Uiso 0.665(5) 1 calc R U P A 1
H78B H 0.369903 0.729213 0.186342 0.257 Uiso 0.665(5) 1 calc R U P A 1
H78C H 0.418128 0.831471 0.238328 0.257 Uiso 0.665(5) 1 calc R U P A 1
C81 C 0.3559(6) 0.7072(9) 0.2758(5) 0.095(5) Uani 0.335(5) 1 d DG U P A 2
C82 C 0.3108(4) 0.6611(8) 0.3101(4) 0.068(3) Uani 0.335(5) 1 d DG U P A 2
C83 C 0.3391(5) 0.5603(8) 0.3516(4) 0.070(3) Uani 0.335(5) 1 d DG U P A 2
H83 H 0.308267 0.528799 0.375090 0.084 Uiso 0.335(5) 1 calc R U P A 2
C84 C 0.4126(5) 0.5055(8) 0.3589(5) 0.087(4) Uani 0.335(5) 1 d DG U P A 2
H84 H 0.431966 0.436584 0.387361 0.105 Uiso 0.335(5) 1 calc R U P A 2
C85 C 0.4577(5) 0.5516(11) 0.3246(5) 0.114(5) Uani 0.335(5) 1 d DG U P A 2
H85 H 0.507933 0.514116 0.329622 0.137 Uiso 0.335(5) 1 calc R U P A 2
C86 C 0.4294(6) 0.6524(10) 0.2831(5) 0.109(4) Uani 0.335(5) 1 d DG U P A 2
H86 H 0.460202 0.683862 0.259610 0.131 Uiso 0.335(5) 1 calc R U P A 2
C87 C 0.3381(12) 0.8254(16) 0.2334(9) 0.139(6) Uani 0.335(5) 1 d D U P A 2
H87A H 0.379791 0.835513 0.214961 0.209 Uiso 0.335(5) 1 calc R U P A 2
H87B H 0.285807 0.816011 0.199163 0.209 Uiso 0.335(5) 1 calc R U P A 2
H87C H 0.337337 0.899978 0.258922 0.209 Uiso 0.335(5) 1 calc R U P A 2
C88 C 0.2329(8) 0.7288(16) 0.3022(8) 0.084(4) Uani 0.335(5) 1 d D U P A 2
H88A H 0.224006 0.796618 0.270773 0.126 Uiso 0.335(5) 1 calc R U P A 2
H88B H 0.188309 0.668593 0.287711 0.126 Uiso 0.335(5) 1 calc R U P A 2
H88C H 0.236030 0.765034 0.343066 0.126 Uiso 0.335(5) 1 calc R U P A 2
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
-2.00 -3.00 -2.00 0.1650
-1.00 0.00 1.00 0.0210
-1.00 0.00 -3.00 0.1340
-1.00 -1.00 -3.00 0.1400
-1.00 -4.00 3.00 0.2100
-1.00 -1.00 -2.00 0.1360
1.00 0.00 -1.00 0.0040
1.00 3.00 2.00 0.1720
1.00 0.00 4.00 0.1750
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
C22 O1 C12 117.78(19) . . ?
C34 O2 C5 117.2(2) . . ?
C52 O3 C42 118.60(18) . . ?
C64 O4 C6 117.6(2) . . ?
C2 N1 C1 116.62(17) . . ?
C2 N1 H1 106.7 . . ?
C1 N1 H1 108.5 . . ?
C3 N2 C4 114.26(17) . . ?
C3 N2 H2 110.0 . . ?
C4 N2 H2 109.9 . . ?
N1 C1 C21 111.38(18) . . ?
N1 C1 C11 107.84(17) . . ?
C21 C1 C11 108.53(18) . . ?
N1 C1 C31 108.59(17) . . ?
C21 C1 C31 110.76(18) . . ?
C11 C1 C31 109.69(18) . . ?
N1 C2 C3 109.37(18) . . ?
N1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N2 C3 C2 111.26(18) . . ?
N2 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N2 C4 C51 107.58(17) . . ?
N2 C4 C41 112.91(17) . . ?
C51 C4 C41 109.19(18) . . ?
N2 C4 C61 108.89(17) . . ?
C51 C4 C61 108.44(17) . . ?
C41 C4 C61 109.73(17) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 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 117.6(2) . . ?
C12 C11 C1 121.1(2) . . ?
C16 C11 C1 121.2(2) . . ?
C11 C12 O1 122.3(2) . . ?
C11 C12 C13 122.0(2) . . ?
O1 C12 C13 115.6(2) . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.1(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C22 C21 C26 116.7(2) . . ?
C22 C21 C1 121.3(2) . . ?
C26 C21 C1 121.8(2) . . ?
O1 C22 C21 122.0(2) . . ?
O1 C22 C23 115.6(2) . . ?
C21 C22 C23 122.3(2) . . ?
C24 C23 C22 119.2(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 121.4(3) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
C32 C31 C36 117.3(2) . . ?
C32 C31 C1 122.6(2) . . ?
C36 C31 C1 120.0(2) . . ?
C31 C32 C33 121.7(2) . . ?
C31 C32 H32 119.1 . . ?
C33 C32 H32 119.1 . . ?
C34 C33 C32 120.0(2) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
O2 C34 C33 125.2(2) . . ?
O2 C34 C35 115.7(2) . . ?
C33 C34 C35 119.1(2) . . ?
C36 C35 C34 120.3(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C31 121.5(2) . . ?
C35 C36 H36 119.3 . . ?
C31 C36 H36 119.3 . . ?
C42 C41 C46 116.8(2) . . ?
C42 C41 C4 122.4(2) . . ?
C46 C41 C4 120.8(2) . . ?
O3 C42 C41 123.0(2) . . ?
O3 C42 C43 114.9(2) . . ?
C41 C42 C43 122.1(2) . . ?
C44 C43 C42 119.5(2) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C43 C44 C45 120.1(2) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C46 119.7(2) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C45 C46 C41 121.7(2) . . ?
C45 C46 H46 119.1 . . ?
C41 C46 H46 119.1 . . ?
C52 C51 C56 117.2(2) . . ?
C52 C51 C4 122.8(2) . . ?
C56 C51 C4 120.0(2) . . ?
C51 C52 O3 122.9(2) . . ?
C51 C52 C53 122.1(2) . . ?
O3 C52 C53 115.0(2) . . ?
C54 C53 C52 119.4(3) . . ?
C54 C53 H53 120.3 . . ?
C52 C53 H53 120.3 . . ?
C53 C54 C55 120.1(2) . . ?
C53 C54 H54 119.9 . . ?
C55 C54 H54 119.9 . . ?
C54 C55 C56 119.8(3) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C55 C56 C51 121.4(3) . . ?
C55 C56 H56 119.3 . . ?
C51 C56 H56 119.3 . . ?
C62 C61 C66 117.7(2) . . ?
C62 C61 C4 122.17(19) . . ?
C66 C61 C4 120.10(19) . . ?
C63 C62 C61 121.0(2) . . ?
C63 C62 H62 119.5 . . ?
C61 C62 H62 119.5 . . ?
C64 C63 C62 120.4(2) . . ?
C64 C63 H63 119.8 . . ?
C62 C63 H63 119.8 . . ?
O4 C64 C65 124.9(2) . . ?
O4 C64 C63 115.6(2) . . ?
C65 C64 C63 119.5(2) . . ?
C64 C65 C66 119.6(2) . . ?
C64 C65 H65 120.2 . . ?
C66 C65 H65 120.2 . . ?
C65 C66 C61 121.8(2) . . ?
C65 C66 H66 119.1 . . ?
C61 C66 H66 119.1 . . ?
C72 C71 C76 120.0 . . ?
C72 C71 C77 121.9(5) . . ?
C76 C71 C77 118.0(5) . . ?
C73 C72 C71 120.0 . . ?
C73 C72 C78 117.4(5) . . ?
C71 C72 C78 122.5(5) . . ?
C74 C73 C72 120.0 . . ?
C74 C73 H73 120.0 . . ?
C72 C73 H73 120.0 . . ?
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 . . ?
C72 C78 H78A 109.5 . . ?
C72 C78 H78B 109.5 . . ?
H78A C78 H78B 109.5 . . ?
C72 C78 H78C 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
C82 C81 C86 120.0 . . ?
C82 C81 C87 126.8(9) . . ?
C86 C81 C87 112.9(9) . . ?
C83 C82 C81 120.0 . . ?
C83 C82 C88 122.5(8) . . ?
C81 C82 C88 117.4(8) . . ?
C82 C83 C84 120.0 . . ?
C82 C83 H83 120.0 . . ?
C84 C83 H83 120.0 . . ?
C83 C84 C85 120.0 . . ?
C83 C84 H84 120.0 . . ?
C85 C84 H84 120.0 . . ?
C86 C85 C84 120.0 . . ?
C86 C85 H85 120.0 . . ?
C84 C85 H85 120.0 . . ?
C85 C86 C81 120.0 . . ?
C85 C86 H86 120.0 . . ?
C81 C86 H86 120.0 . . ?
C81 C87 H87A 109.5 . . ?
C81 C87 H87B 109.5 . . ?
H87A C87 H87B 109.5 . . ?
C81 C87 H87C 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
C82 C88 H88A 109.5 . . ?
C82 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C82 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 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 C22 1.380(3) . ?
O1 C12 1.385(3) . ?
O2 C34 1.371(3) . ?
O2 C5 1.422(3) . ?
O3 C52 1.382(3) . ?
O3 C42 1.382(3) . ?
O4 C64 1.372(3) . ?
O4 C6 1.425(3) . ?
N1 C2 1.461(3) . ?
N1 C1 1.482(3) . ?
N1 H1 0.8827 . ?
N2 C3 1.471(3) . ?
N2 C4 1.476(3) . ?
N2 H2 0.8146 . ?
C1 C21 1.527(3) . ?
C1 C11 1.530(3) . ?
C1 C31 1.531(3) . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C51 1.528(3) . ?
C4 C41 1.532(3) . ?
C4 C61 1.540(3) . ?
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 1.384(3) . ?
C11 C16 1.391(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.373(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.386(3) . ?
C21 C26 1.399(3) . ?
C22 C23 1.391(4) . ?
C23 C24 1.372(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.380(3) . ?
C31 C36 1.396(3) . ?
C32 C33 1.394(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.377(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(4) . ?
C35 C36 1.376(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.385(3) . ?
C41 C46 1.396(3) . ?
C42 C43 1.390(3) . ?
C43 C44 1.373(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.381(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.382(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.380(3) . ?
C51 C56 1.400(3) . ?
C52 C53 1.392(3) . ?
C53 C54 1.376(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.381(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.385(4) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C62 1.389(3) . ?
C61 C66 1.392(3) . ?
C62 C63 1.386(3) . ?
C62 H62 0.9500 . ?
C63 C64 1.384(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.383(3) . ?
C65 C66 1.385(3) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C71 C72 1.3900 . ?
C71 C76 1.3900 . ?
C71 C77 1.512(9) . ?
C72 C73 1.3900 . ?
C72 C78 1.517(8) . ?
C73 C74 1.3900 . ?
C73 H73 0.9500 . ?
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 . ?
C81 C82 1.3900 . ?
C81 C86 1.3900 . ?
C81 C87 1.536(13) . ?
C82 C83 1.3900 . ?
C82 C88 1.518(12) . ?
C83 C84 1.3900 . ?
C83 H83 0.9500 . ?
C84 C85 1.3900 . ?
C84 H84 0.9500 . ?
C85 C86 1.3900 . ?
C85 H85 0.9500 . ?
C86 H86 0.9500 . ?
C87 H87A 0.9800 . ?
C87 H87B 0.9800 . ?
C87 H87C 0.9800 . ?
C88 H88A 0.9800 . ?
C88 H88B 0.9800 . ?
C88 H88C 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
N1 H1 N2 0.88 2.61 2.945(3) 104 . yes
C32 H32 N1 0.95 2.38 2.764(3) 104 . yes
C53 H53 O4 0.95 2.57 3.375(3) 143 1_565 yes
C62 H62 N2 0.95 2.45 2.804(3) 102 . 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 -60.5(2) . . . . ?
C2 N1 C1 C11 58.5(2) . . . . ?
C2 N1 C1 C31 177.25(18) . . . . ?
C1 N1 C2 C3 -174.67(18) . . . . ?
C4 N2 C3 C2 157.48(18) . . . . ?
N1 C2 C3 N2 -66.6(2) . . . . ?
C3 N2 C4 C51 -73.0(2) . . . . ?
C3 N2 C4 C41 47.5(2) . . . . ?
C3 N2 C4 C61 169.63(17) . . . . ?
N1 C1 C11 C12 -100.4(2) . . . . ?
C21 C1 C11 C12 20.4(3) . . . . ?
C31 C1 C11 C12 141.6(2) . . . . ?
N1 C1 C11 C16 76.6(3) . . . . ?
C21 C1 C11 C16 -162.6(2) . . . . ?
C31 C1 C11 C16 -41.5(3) . . . . ?
C16 C11 C12 O1 -176.9(2) . . . . ?
C1 C11 C12 O1 0.2(3) . . . . ?
C16 C11 C12 C13 1.8(3) . . . . ?
C1 C11 C12 C13 178.9(2) . . . . ?
C22 O1 C12 C11 -20.1(3) . . . . ?
C22 O1 C12 C13 161.1(2) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
O1 C12 C13 C14 177.9(2) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C13 C14 C15 C16 1.7(4) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
C1 C11 C16 C15 -178.1(2) . . . . ?
N1 C1 C21 C22 94.5(2) . . . . ?
C11 C1 C21 C22 -24.0(3) . . . . ?
C31 C1 C21 C22 -144.5(2) . . . . ?
N1 C1 C21 C26 -81.0(3) . . . . ?
C11 C1 C21 C26 160.5(2) . . . . ?
C31 C1 C21 C26 40.0(3) . . . . ?
C12 O1 C22 C21 16.3(3) . . . . ?
C12 O1 C22 C23 -163.2(2) . . . . ?
C26 C21 C22 O1 -177.1(2) . . . . ?
C1 C21 C22 O1 7.2(3) . . . . ?
C26 C21 C22 C23 2.3(3) . . . . ?
C1 C21 C22 C23 -173.4(2) . . . . ?
O1 C22 C23 C24 176.8(2) . . . . ?
C21 C22 C23 C24 -2.7(4) . . . . ?
C22 C23 C24 C25 1.1(4) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C24 C25 C26 C21 -1.0(4) . . . . ?
C22 C21 C26 C25 -0.5(4) . . . . ?
C1 C21 C26 C25 175.2(2) . . . . ?
N1 C1 C31 C32 -7.8(3) . . . . ?
C21 C1 C31 C32 -130.4(2) . . . . ?
C11 C1 C31 C32 109.9(2) . . . . ?
N1 C1 C31 C36 174.7(2) . . . . ?
C21 C1 C31 C36 52.1(3) . . . . ?
C11 C1 C31 C36 -67.7(3) . . . . ?
C36 C31 C32 C33 -1.0(4) . . . . ?
C1 C31 C32 C33 -178.6(2) . . . . ?
C31 C32 C33 C34 0.6(4) . . . . ?
C5 O2 C34 C33 -8.1(4) . . . . ?
C5 O2 C34 C35 172.3(2) . . . . ?
C32 C33 C34 O2 -179.2(2) . . . . ?
C32 C33 C34 C35 0.4(4) . . . . ?
O2 C34 C35 C36 178.6(2) . . . . ?
C33 C34 C35 C36 -1.0(4) . . . . ?
C34 C35 C36 C31 0.7(4) . . . . ?
C32 C31 C36 C35 0.3(4) . . . . ?
C1 C31 C36 C35 178.0(2) . . . . ?
N2 C4 C41 C42 -128.6(2) . . . . ?
C51 C4 C41 C42 -9.0(3) . . . . ?
C61 C4 C41 C42 109.7(2) . . . . ?
N2 C4 C41 C46 51.5(3) . . . . ?
C51 C4 C41 C46 171.2(2) . . . . ?
C61 C4 C41 C46 -70.1(3) . . . . ?
C52 O3 C42 C41 7.9(3) . . . . ?
C52 O3 C42 C43 -172.6(2) . . . . ?
C46 C41 C42 O3 -179.3(2) . . . . ?
C4 C41 C42 O3 0.9(3) . . . . ?
C46 C41 C42 C43 1.3(3) . . . . ?
C4 C41 C42 C43 -178.5(2) . . . . ?
O3 C42 C43 C44 179.2(2) . . . . ?
C41 C42 C43 C44 -1.4(4) . . . . ?
C42 C43 C44 C45 0.1(4) . . . . ?
C43 C44 C45 C46 1.2(4) . . . . ?
C44 C45 C46 C41 -1.3(4) . . . . ?
C42 C41 C46 C45 0.0(3) . . . . ?
C4 C41 C46 C45 179.8(2) . . . . ?
N2 C4 C51 C52 132.4(2) . . . . ?
C41 C4 C51 C52 9.6(3) . . . . ?
C61 C4 C51 C52 -110.0(2) . . . . ?
N2 C4 C51 C56 -48.6(3) . . . . ?
C41 C4 C51 C56 -171.42(19) . . . . ?
C61 C4 C51 C56 69.1(2) . . . . ?
C56 C51 C52 O3 179.0(2) . . . . ?
C4 C51 C52 O3 -2.0(3) . . . . ?
C56 C51 C52 C53 -0.8(3) . . . . ?
C4 C51 C52 C53 178.2(2) . . . . ?
C42 O3 C52 C51 -7.4(3) . . . . ?
C42 O3 C52 C53 172.4(2) . . . . ?
C51 C52 C53 C54 1.1(4) . . . . ?
O3 C52 C53 C54 -178.8(2) . . . . ?
C52 C53 C54 C55 -0.4(4) . . . . ?
C53 C54 C55 C56 -0.4(4) . . . . ?
C54 C55 C56 C51 0.6(4) . . . . ?
C52 C51 C56 C55 0.0(3) . . . . ?
C4 C51 C56 C55 -179.0(2) . . . . ?
N2 C4 C61 C62 20.4(3) . . . . ?
C51 C4 C61 C62 -96.4(2) . . . . ?
C41 C4 C61 C62 144.5(2) . . . . ?
N2 C4 C61 C66 -162.69(19) . . . . ?
C51 C4 C61 C66 80.5(2) . . . . ?
C41 C4 C61 C66 -38.7(3) . . . . ?
C66 C61 C62 C63 0.3(3) . . . . ?
C4 C61 C62 C63 177.3(2) . . . . ?
C61 C62 C63 C64 -0.8(3) . . . . ?
C6 O4 C64 C65 -3.4(3) . . . . ?
C6 O4 C64 C63 177.0(2) . . . . ?
C62 C63 C64 O4 -179.6(2) . . . . ?
C62 C63 C64 C65 0.7(3) . . . . ?
O4 C64 C65 C66 -179.7(2) . . . . ?
C63 C64 C65 C66 -0.2(3) . . . . ?
C64 C65 C66 C61 -0.3(3) . . . . ?
C62 C61 C66 C65 0.2(3) . . . . ?
C4 C61 C66 C65 -176.8(2) . . . . ?
C76 C71 C72 C73 0.0 . . . . ?
C77 C71 C72 C73 -178.5(7) . . . . ?
C76 C71 C72 C78 -175.9(7) . . . . ?
C77 C71 C72 C78 5.6(9) . . . . ?
C71 C72 C73 C74 0.0 . . . . ?
C78 C72 C73 C74 176.1(7) . . . . ?
C72 C73 C74 C75 0.0 . . . . ?
C73 C74 C75 C76 0.0 . . . . ?
C74 C75 C76 C71 0.0 . . . . ?
C72 C71 C76 C75 0.0 . . . . ?
C77 C71 C76 C75 178.6(7) . . . . ?
C86 C81 C82 C83 0.0 . . . . ?
C87 C81 C82 C83 -173.2(14) . . . . ?
C86 C81 C82 C88 177.3(11) . . . . ?
C87 C81 C82 C88 4.1(14) . . . . ?
C81 C82 C83 C84 0.0 . . . . ?
C88 C82 C83 C84 -177.1(12) . . . . ?
C82 C83 C84 C85 0.0 . . . . ?
C83 C84 C85 C86 0.0 . . . . ?
C84 C85 C86 C81 0.0 . . . . ?
C82 C81 C86 C85 0.0 . . . . ?
C87 C81 C86 C85 174.1(12) . . . . ?
