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#$Date: 2025-11-05 02:35:28 +0200 (Wed, 05 Nov 2025) $
#$Revision: 303173 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/12/7251218.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_7251218
loop_
_publ_author_name
'Trollip, Danica B.'
'Barton, Benita'
'Caira, Mino R.'
'Hosten, Eric Cyriel'
_publ_section_title
;
 Chloro-containing host compounds with fused tricyclic moieties and
 diamino linkers: host ability and affinity behaviour in
 pyridine/methylpyridines
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00969C
_journal_year                    2025
_chemical_formula_moiety         'C40 H30 Cl2 N2 O2, 2(C6 H7 N)'
_chemical_formula_sum            'C52 H44 Cl2 N4 O2'
_chemical_formula_weight         827.81
_chemical_melting_point          'onset of decomposition at 341 K'
_chemical_name_common            none
_chemical_name_systematic
'N,N?-Bis(9-(4-chlorophenyl)-9-xanthenyl)ethylenediamine 4-methylpyridine clathrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-06-10 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.2790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8825(6)
_cell_length_b                   11.6416(4)
_cell_length_c                   24.0763(8)
_cell_measurement_reflns_used    9359
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.23
_cell_volume                     4127.9(3)
_computing_cell_refinement
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_data_collection       'Apex3 v2019.1-0, Bruker (2019).'
_computing_data_reduction
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_molecular_graphics
'POV-Ray in interface X-Seed (LJ Barbour, 1999)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-Version 2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean n/a
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE SCXRD diffractometer'
_diffrn_measurement_method       'omega-and phi-scans, width 1.00 deg.'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            195964
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.373
_diffrn_reflns_theta_min         1.947
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.7114
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       plate
_exptl_crystal_F_000             1736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 4-methylpyridine'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.047
_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     551
_refine_ls_number_reflns         10302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0373
_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)+(0.0435P)²+2.1111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8413
_reflns_number_total             10302
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00969c2.cif
_cod_data_source_block           C_8OF12
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7251218
_shelx_shelxl_version_number     2019/3
_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   0.930
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.46682(9) 0.68892(12) 0.38141(6) 0.0216(3) Uani 1 1 d . . . . .
H1 H 0.469559 0.614284 0.365785 0.026 Uiso 1 1 calc R U . . .
C2 C 0.54635(9) 0.75016(13) 0.39642(6) 0.0271(3) Uani 1 1 d . . . . .
H2 H 0.603020 0.717455 0.391212 0.032 Uiso 1 1 calc R U . . .
C3 C 0.54311(10) 0.85973(13) 0.41917(6) 0.0273(3) Uani 1 1 d . . . . .
H3 H 0.597634 0.901909 0.429374 0.033 Uiso 1 1 calc R U . . .
C4 C 0.46106(10) 0.90714(12) 0.42691(6) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.458611 0.981981 0.442352 0.027 Uiso 1 1 calc R U . . .
C5 C 0.38137(9) 0.84392(11) 0.41180(5) 0.0166(2) Uani 1 1 d . . . . .
C6 C 0.38250(8) 0.73484(10) 0.38881(5) 0.0148(2) Uani 1 1 d . . . . .
C7 C 0.29464(8) 0.67079(10) 0.36756(5) 0.0128(2) Uani 1 1 d . . . . .
C8 C 0.21654(8) 0.72466(10) 0.39298(5) 0.0141(2) Uani 1 1 d . . . . .
C9 C 0.13380(9) 0.66721(11) 0.39166(5) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.126766 0.593066 0.375123 0.024 Uiso 1 1 calc R U . . .
C10 C 0.06188(9) 0.71572(13) 0.41386(6) 0.0250(3) Uani 1 1 d . . . . .
H10 H 0.006071 0.675398 0.412259 0.030 Uiso 1 1 calc R U . . .
C11 C 0.07179(10) 0.82377(13) 0.43852(6) 0.0250(3) Uani 1 1 d . . . . .
H11 H 0.022728 0.857293 0.453985 0.030 Uiso 1 1 calc R U . . .
C12 C 0.15287(9) 0.88254(12) 0.44059(5) 0.0225(3) Uani 1 1 d . . . . .
H12 H 0.159788 0.956419 0.457417 0.027 Uiso 1 1 calc R U . . .
C13 C 0.22439(9) 0.83258(11) 0.41779(5) 0.0164(2) Uani 1 1 d . . . . .
O14 O 0.30255(6) 0.89780(8) 0.42138(4) 0.01978(19) Uani 1 1 d . . . . .
C15 C 0.30233(8) 0.54419(10) 0.38544(5) 0.0136(2) Uani 1 1 d . . . . .
C16 C 0.32878(8) 0.51740(11) 0.44209(5) 0.0162(2) Uani 1 1 d . . . . .
H16 H 0.345071 0.577519 0.468292 0.019 Uiso 1 1 calc R U . . .
C17 C 0.33160(9) 0.40444(11) 0.46058(5) 0.0178(2) Uani 1 1 d . . . . .
H17 H 0.350037 0.386853 0.499068 0.021 Uiso 1 1 calc R U . . .
C18 C 0.30699(8) 0.31743(10) 0.42186(5) 0.0164(2) Uani 1 1 d . . . . .
C19 C 0.28088(8) 0.34111(10) 0.36573(5) 0.0166(2) Uani 1 1 d . . . . .
H19 H 0.264496 0.280651 0.339734 0.020 Uiso 1 1 calc R U . . .
C20 C 0.27888(8) 0.45515(10) 0.34762(5) 0.0153(2) Uani 1 1 d . . . . .
H20 H 0.261270 0.472127 0.308992 0.018 Uiso 1 1 calc R U . . .
Cl21 Cl 0.30819(2) 0.17496(3) 0.44446(2) 0.02250(8) Uani 1 1 d . . . . .
N22 N 0.27345(7) 0.67706(9) 0.30541(4) 0.0142(2) Uani 1 1 d . . . . .
H22 H 0.3171(10) 0.6415(13) 0.2914(6) 0.015(4) Uiso 1 1 d . . . . .
C23 C 0.26551(9) 0.79427(10) 0.28297(5) 0.0160(2) Uani 1 1 d . . . . .
H23A H 0.321738 0.837662 0.296195 0.019 Uiso 1 1 calc R U . . .
H23B H 0.214139 0.833984 0.296688 0.019 Uiso 1 1 calc R U . . .
C24 C 0.24997(9) 0.79087(10) 0.21914(5) 0.0158(2) Uani 1 1 d . . . . .
H24A H 0.301593 0.751814 0.205385 0.019 Uiso 1 1 calc R U . . .
H24B H 0.194010 0.746954 0.205892 0.019 Uiso 1 1 calc R U . . .
N25 N 0.24126(7) 0.90837(9) 0.19686(4) 0.0139(2) Uani 1 1 d . . . . .
H25 H 0.1980(11) 0.9436(13) 0.2128(6) 0.019(4) Uiso 1 1 d . . . . .
C26 C 0.37101(8) 0.91300(11) 0.10719(5) 0.0173(2) Uani 1 1 d . . . . .
H26 H 0.382070 0.984175 0.126256 0.021 Uiso 1 1 calc R U . . .
C27 C 0.43911(9) 0.86437(12) 0.08119(5) 0.0201(3) Uani 1 1 d . . . . .
H27 H 0.496256 0.901543 0.082797 0.024 Uiso 1 1 calc R U . . .
C28 C 0.42306(9) 0.76045(12) 0.05266(5) 0.0206(3) Uani 1 1 d . . . . .
H28 H 0.469124 0.727121 0.034324 0.025 Uiso 1 1 calc R U . . .
C29 C 0.34021(9) 0.70584(11) 0.05101(5) 0.0187(3) Uani 1 1 d . . . . .
H29 H 0.329235 0.634932 0.031700 0.022 Uiso 1 1 calc R U . . .
C30 C 0.27271(8) 0.75565(10) 0.07795(5) 0.0156(2) Uani 1 1 d . . . . .
C31 C 0.28648(8) 0.85996(10) 0.10607(5) 0.0134(2) Uani 1 1 d . . . . .
C32 C 0.21294(8) 0.91495(10) 0.13526(5) 0.0126(2) Uani 1 1 d . . . . .
C33 C 0.12291(8) 0.85289(10) 0.11813(5) 0.0143(2) Uani 1 1 d . . . . .
C34 C 0.04256(9) 0.89740(11) 0.13315(6) 0.0206(3) Uani 1 1 d . . . . .
H34 H 0.043591 0.970540 0.150723 0.025 Uiso 1 1 calc R U . . .
C35 C -0.03843(9) 0.83749(12) 0.12303(6) 0.0245(3) Uani 1 1 d . . . . .
H35 H -0.092286 0.869348 0.133541 0.029 Uiso 1 1 calc R U . . .
C36 C -0.04045(9) 0.73029(12) 0.09736(6) 0.0229(3) Uani 1 1 d . . . . .
H36 H -0.095837 0.688640 0.090519 0.028 Uiso 1 1 calc R U . . .
C37 C 0.03755(9) 0.68419(11) 0.08179(5) 0.0207(3) Uani 1 1 d . . . . .
H37 H 0.036180 0.611011 0.064224 0.025 Uiso 1 1 calc R U . . .
C38 C 0.11872(8) 0.74627(11) 0.09213(5) 0.0161(2) Uani 1 1 d . . . . .
O39 O 0.19338(6) 0.69350(8) 0.07534(4) 0.01931(19) Uani 1 1 d . . . . .
C40 C 0.20387(8) 1.04187(10) 0.11773(5) 0.0134(2) Uani 1 1 d . . . . .
C41 C 0.17120(9) 1.06906(11) 0.06186(5) 0.0164(2) Uani 1 1 d . . . . .
H41 H 0.153412 1.009038 0.035858 0.020 Uiso 1 1 calc R U . . .
C42 C 0.16438(9) 1.18245(11) 0.04384(5) 0.0180(2) Uani 1 1 d . . . . .
H42 H 0.142315 1.200375 0.005826 0.022 Uiso 1 1 calc R U . . .
C43 C 0.19042(8) 1.26910(10) 0.08240(5) 0.0165(2) Uani 1 1 d . . . . .
C44 C 0.22293(8) 1.24524(10) 0.13781(5) 0.0172(2) Uani 1 1 d . . . . .
H44 H 0.240384 1.305578 0.163690 0.021 Uiso 1 1 calc R U . . .
C45 C 0.22965(8) 1.13055(10) 0.15509(5) 0.0160(2) Uani 1 1 d . . . . .
H45 H 0.252269 1.113065 0.193081 0.019 Uiso 1 1 calc R U . . .
Cl46 Cl 0.18235(2) 1.41256(3) 0.06072(2) 0.02209(8) Uani 1 1 d . . . . .
N47 N 0.36269(9) 0.43706(12) 0.22660(6) 0.0322(3) Uani 1 1 d . . . . .
C48 C 0.44377(11) 0.41190(14) 0.25622(7) 0.0347(4) Uani 1 1 d . . . . .
H48 H 0.445877 0.354295 0.284322 0.042 Uiso 1 1 calc R U . . .
C49 C 0.52430(10) 0.46431(13) 0.24850(6) 0.0259(3) Uani 1 1 d . . . . .
H49 H 0.579856 0.441526 0.270203 0.031 Uiso 1 1 calc R U . . .
C50 C 0.52310(9) 0.55032(11) 0.20880(6) 0.0206(3) Uani 1 1 d . . . . .
C51 C 0.43935(10) 0.57955(12) 0.17915(6) 0.0237(3) Uani 1 1 d . . . . .
H51 H 0.434764 0.639998 0.152388 0.028 Uiso 1 1 calc R U . . .
C52 C 0.36274(9) 0.52043(13) 0.18870(6) 0.0250(3) Uani 1 1 d . . . . .
H52 H 0.306535 0.540401 0.166915 0.030 Uiso 1 1 calc R U . . .
C53 C 0.60864(11) 0.60862(15) 0.19762(8) 0.0368(4) Uani 1 1 d . . . . .
H53A H 0.627388 0.665137 0.227190 0.055 Uiso 1 1 calc R U . . .
H53B H 0.597675 0.647541 0.161178 0.055 Uiso 1 1 calc R U . . .
H53C H 0.656729 0.551254 0.197186 0.055 Uiso 1 1 calc R U . . .
N54 N 0.13621(9) 1.14735(13) 0.27131(6) 0.0357(3) Uani 1 1 d . . . . .
C55 C 0.13322(10) 1.05790(13) 0.30548(6) 0.0271(3) Uani 1 1 d . . . . .
H55 H 0.188536 1.032652 0.326620 0.033 Uiso 1 1 calc R U . . .
C56 C 0.05481(10) 0.99974(12) 0.31203(6) 0.0245(3) Uani 1 1 d . . . . .
H56 H 0.057281 0.934386 0.335826 0.029 Uiso 1 1 calc R U . . .
C57 C -0.02791(9) 1.03720(12) 0.28363(6) 0.0214(3) Uani 1 1 d . . . . .
C58 C -0.02581(10) 1.12979(13) 0.24802(6) 0.0272(3) Uani 1 1 d . . . . .
H58 H -0.080418 1.158700 0.227492 0.033 Uiso 1 1 calc R U . . .
C59 C 0.05646(12) 1.17987(15) 0.24258(7) 0.0378(4) Uani 1 1 d . . . . .
H59 H 0.056568 1.241519 0.216741 0.045 Uiso 1 1 calc R U . . .
C60 C -0.11577(11) 0.98106(16) 0.29171(8) 0.0384(4) Uani 1 1 d . . . . .
H60A H -0.164641 1.038176 0.286619 0.058 Uiso 1 1 calc R U . . .
H60B H -0.110525 0.948978 0.329674 0.058 Uiso 1 1 calc R U . . .
H60C H -0.129580 0.919331 0.264128 0.058 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C2 C1 C6 121.26(13) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 119.87(13) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.15(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.28(13) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
O14 C5 C6 122.89(11) . . ?
O14 C5 C4 115.29(11) . . ?
C6 C5 C4 121.82(12) . . ?
C5 C6 C1 117.62(12) . . ?
C5 C6 C7 121.45(11) . . ?
C1 C6 C7 120.73(11) . . ?
N22 C7 C8 108.70(9) . . ?
N22 C7 C6 111.13(9) . . ?
C8 C7 C6 109.27(10) . . ?
N22 C7 C15 109.03(9) . . ?
C8 C7 C15 108.22(9) . . ?
C6 C7 C15 110.42(10) . . ?
C13 C8 C9 117.52(11) . . ?
C13 C8 C7 121.54(11) . . ?
C9 C8 C7 120.94(11) . . ?
C10 C9 C8 121.59(12) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.60(13) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.13(12) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.46(13) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
O14 C13 C8 122.83(11) . . ?
O14 C13 C12 115.47(11) . . ?
C8 C13 C12 121.70(12) . . ?
C5 O14 C13 117.94(10) . . ?
C20 C15 C16 118.76(11) . . ?
C20 C15 C7 122.03(10) . . ?
C16 C15 C7 119.11(10) . . ?
C17 C16 C15 121.03(11) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 118.87(11) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C17 121.44(11) . . ?
C19 C18 Cl21 118.96(10) . . ?
C17 C18 Cl21 119.59(10) . . ?
C18 C19 C20 119.10(11) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C15 C20 C19 120.81(11) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C23 N22 C7 114.27(9) . . ?
C23 N22 H22 108.8(10) . . ?
C7 N22 H22 107.6(10) . . ?
N22 C23 C24 109.91(10) . . ?
N22 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
N22 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
N25 C24 C23 109.72(10) . . ?
N25 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
N25 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
C24 N25 C32 114.24(9) . . ?
C24 N25 H25 107.5(10) . . ?
C32 N25 H25 106.7(10) . . ?
C27 C26 C31 121.68(12) . . ?
C27 C26 H26 119.2 . . ?
C31 C26 H26 119.2 . . ?
C26 C27 C28 119.48(12) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 120.11(12) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 119.57(12) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
O39 C30 C31 123.07(11) . . ?
O39 C30 C29 115.41(11) . . ?
C31 C30 C29 121.51(12) . . ?
C30 C31 C26 117.65(11) . . ?
C30 C31 C32 121.73(11) . . ?
C26 C31 C32 120.62(11) . . ?
N25 C32 C31 108.64(9) . . ?
N25 C32 C33 110.96(9) . . ?
C31 C32 C33 109.71(10) . . ?
N25 C32 C40 108.97(9) . . ?
C31 C32 C40 108.51(9) . . ?
C33 C32 C40 109.99(10) . . ?
C38 C33 C34 117.63(11) . . ?
C38 C33 C32 121.75(11) . . ?
C34 C33 C32 120.34(11) . . ?
C35 C34 C33 121.58(13) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C34 C35 C36 119.54(13) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C37 C36 C35 120.31(12) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 119.33(12) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
O39 C38 C33 123.00(11) . . ?
O39 C38 C37 115.40(11) . . ?
C33 C38 C37 121.60(12) . . ?
C30 O39 C38 118.25(10) . . ?
C45 C40 C41 118.73(11) . . ?
C45 C40 C32 122.16(10) . . ?
C41 C40 C32 119.08(10) . . ?
C42 C41 C40 121.00(12) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C43 C42 C41 118.76(11) . . ?
C43 C42 H42 120.6 . . ?
C41 C42 H42 120.6 . . ?
C44 C43 C42 121.71(11) . . ?
C44 C43 Cl46 118.70(10) . . ?
C42 C43 Cl46 119.59(10) . . ?
C43 C44 C45 118.69(12) . . ?
C43 C44 H44 120.7 . . ?
C45 C44 H44 120.7 . . ?
C40 C45 C44 121.11(11) . . ?
C40 C45 H45 119.4 . . ?
C44 C45 H45 119.4 . . ?
C52 N47 C48 115.70(13) . . ?
N47 C48 C49 124.28(14) . . ?
N47 C48 H48 117.9 . . ?
C49 C48 H48 117.9 . . ?
C48 C49 C50 119.19(13) . . ?
C48 C49 H49 120.4 . . ?
C50 C49 H49 120.4 . . ?
C49 C50 C51 117.05(13) . . ?
C49 C50 C53 121.64(13) . . ?
C51 C50 C53 121.31(13) . . ?
C52 C51 C50 119.68(13) . . ?
C52 C51 H51 120.2 . . ?
C50 C51 H51 120.2 . . ?
N47 C52 C51 124.04(13) . . ?
N47 C52 H52 118.0 . . ?
C51 C52 H52 118.0 . . ?
C50 C53 H53A 109.5 . . ?
C50 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C50 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C55 N54 C59 115.72(13) . . ?
N54 C55 C56 124.00(14) . . ?
N54 C55 H55 118.0 . . ?
C56 C55 H55 118.0 . . ?
C55 C56 C57 119.63(13) . . ?
C55 C56 H56 120.2 . . ?
C57 C56 H56 120.2 . . ?
C58 C57 C56 116.93(13) . . ?
C58 C57 C60 121.28(13) . . ?
C56 C57 C60 121.78(13) . . ?
C59 C58 C57 119.27(14) . . ?
C59 C58 H58 120.4 . . ?
C57 C58 H58 120.4 . . ?
N54 C59 C58 124.35(15) . . ?
N54 C59 H59 117.8 . . ?
C58 C59 H59 117.8 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C57 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
_geom_bond_publ_flag
C1 C2 1.3845(19) . ?
C1 C6 1.3988(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3988(18) . ?
C4 H4 0.9500 . ?
C5 O14 1.3785(15) . ?
C5 C6 1.3864(17) . ?
C6 C7 1.5279(16) . ?
C7 N22 1.4858(15) . ?
C7 C8 1.5245(16) . ?
C7 C15 1.5352(16) . ?
C8 C13 1.3886(17) . ?
C8 C9 1.3976(17) . ?
C9 C10 1.3839(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3931(18) . ?
C12 H12 0.9500 . ?
C13 O14 1.3814(15) . ?
C15 C20 1.3906(17) . ?
C15 C16 1.3991(16) . ?
C16 C17 1.3871(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3896(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3793(18) . ?
C18 Cl21 1.7449(12) . ?
C19 C20 1.3964(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N22 C23 1.4661(15) . ?
N22 H22 0.878(16) . ?
C23 C24 1.5212(16) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N25 1.4683(15) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N25 C32 1.4842(15) . ?
N25 H25 0.895(16) . ?
C26 C27 1.3864(18) . ?
C26 C31 1.3983(17) . ?
C26 H26 0.9500 . ?
C27 C28 1.3949(19) . ?
C27 H27 0.9500 . ?
C28 C29 1.3827(19) . ?
C28 H28 0.9500 . ?
C29 C30 1.3977(17) . ?
C29 H29 0.9500 . ?
C30 O39 1.3783(15) . ?
C30 C31 1.3911(17) . ?
C31 C32 1.5242(16) . ?
C32 C33 1.5259(16) . ?
C32 C40 1.5372(16) . ?
C33 C38 1.3875(17) . ?
C33 C34 1.3978(17) . ?
C34 C35 1.3834(19) . ?
C34 H34 0.9500 . ?
C35 C36 1.391(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.379(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.3990(17) . ?
C37 H37 0.9500 . ?
C38 O39 1.3801(15) . ?
C40 C45 1.3867(17) . ?
C40 C41 1.3992(16) . ?
C41 C42 1.3887(17) . ?
C41 H41 0.9500 . ?
C42 C43 1.3878(18) . ?
C42 H42 0.9500 . ?
C43 C44 1.3802(18) . ?
C43 Cl46 1.7488(12) . ?
C44 C45 1.3978(17) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
N47 C52 1.332(2) . ?
N47 C48 1.343(2) . ?
C48 C49 1.381(2) . ?
C48 H48 0.9500 . ?
C49 C50 1.3827(19) . ?
C49 H49 0.9500 . ?
C50 C51 1.3865(19) . ?
C50 C53 1.501(2) . ?
C51 C52 1.379(2) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
N54 C55 1.332(2) . ?
N54 C59 1.339(2) . ?
C55 C56 1.378(2) . ?
C55 H55 0.9500 . ?
C56 C57 1.3896(19) . ?
C56 H56 0.9500 . ?
C57 C58 1.3803(19) . ?
C57 C60 1.499(2) . ?
C58 C59 1.379(2) . ?
C58 H58 0.9500 . ?
C59 H59 0.9500 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 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
C12 H12 Cl46 0.95 2.90 3.7259(14) 146.6 4_586 yes
C29 H29 O14 0.95 2.66 3.3178(15) 127.2 4_575 yes
C44 H44 N47 0.95 2.68 3.5500(19) 153.4 1_565 yes
C49 H49 N25 0.95 2.69 3.6064(18) 161.2 2_645 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
C6 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 O14 179.59(11) . . . . ?
C3 C4 C5 C6 -0.46(19) . . . . ?
O14 C5 C6 C1 -179.63(11) . . . . ?
C4 C5 C6 C1 0.43(18) . . . . ?
O14 C5 C6 C7 5.54(17) . . . . ?
C4 C5 C6 C7 -174.41(11) . . . . ?
C2 C1 C6 C5 -0.08(19) . . . . ?
C2 C1 C6 C7 174.79(12) . . . . ?
C5 C6 C7 N22 101.31(12) . . . . ?
C1 C6 C7 N22 -73.37(14) . . . . ?
C5 C6 C7 C8 -18.64(15) . . . . ?
C1 C6 C7 C8 166.68(11) . . . . ?
C5 C6 C7 C15 -137.57(11) . . . . ?
C1 C6 C7 C15 47.76(15) . . . . ?
N22 C7 C8 C13 -105.33(12) . . . . ?
C6 C7 C8 C13 16.11(15) . . . . ?
C15 C7 C8 C13 136.39(11) . . . . ?
N22 C7 C8 C9 74.08(14) . . . . ?
C6 C7 C8 C9 -164.48(11) . . . . ?
C15 C7 C8 C9 -44.20(15) . . . . ?
C13 C8 C9 C10 0.36(19) . . . . ?
C7 C8 C9 C10 -179.08(12) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C9 C8 C13 O14 -179.70(11) . . . . ?
C7 C8 C13 O14 -0.28(18) . . . . ?
C9 C8 C13 C12 -0.05(18) . . . . ?
C7 C8 C13 C12 179.38(11) . . . . ?
C11 C12 C13 O14 179.56(11) . . . . ?
C11 C12 C13 C8 -0.12(19) . . . . ?
C6 C5 O14 C13 12.42(17) . . . . ?
C4 C5 O14 C13 -167.63(11) . . . . ?
C8 C13 O14 C5 -15.12(17) . . . . ?
C12 C13 O14 C5 165.21(11) . . . . ?
N22 C7 C15 C20 -8.51(15) . . . . ?
C8 C7 C15 C20 109.57(12) . . . . ?
C6 C7 C15 C20 -130.88(12) . . . . ?
N22 C7 C15 C16 175.22(10) . . . . ?
C8 C7 C15 C16 -66.71(14) . . . . ?
C6 C7 C15 C16 52.85(14) . . . . ?
C20 C15 C16 C17 -0.12(18) . . . . ?
C7 C15 C16 C17 176.28(11) . . . . ?
C15 C16 C17 C18 -0.45(19) . . . . ?
C16 C17 C18 C19 0.65(19) . . . . ?
C16 C17 C18 Cl21 -178.91(10) . . . . ?
C17 C18 C19 C20 -0.27(19) . . . . ?
Cl21 C18 C19 C20 179.29(9) . . . . ?
C16 C15 C20 C19 0.51(18) . . . . ?
C7 C15 C20 C19 -175.78(11) . . . . ?
C18 C19 C20 C15 -0.32(18) . . . . ?
C8 C7 N22 C23 62.98(13) . . . . ?
C6 C7 N22 C23 -57.31(13) . . . . ?
C15 C7 N22 C23 -179.25(10) . . . . ?
C7 N22 C23 C24 176.31(10) . . . . ?
N22 C23 C24 N25 179.51(10) . . . . ?
C23 C24 N25 C32 -171.76(10) . . . . ?
C31 C26 C27 C28 0.62(19) . . . . ?
C26 C27 C28 C29 -0.83(19) . . . . ?
C27 C28 C29 C30 0.20(19) . . . . ?
C28 C29 C30 O39 -178.30(11) . . . . ?
C28 C29 C30 C31 0.66(18) . . . . ?
O39 C30 C31 C26 178.02(11) . . . . ?
C29 C30 C31 C26 -0.86(17) . . . . ?
O39 C30 C31 C32 -1.43(17) . . . . ?
C29 C30 C31 C32 179.69(11) . . . . ?
C27 C26 C31 C30 0.21(18) . . . . ?
C27 C26 C31 C32 179.67(11) . . . . ?
C24 N25 C32 C31 -63.50(12) . . . . ?
C24 N25 C32 C33 57.19(13) . . . . ?
C24 N25 C32 C40 178.44(10) . . . . ?
C30 C31 C32 N25 109.86(12) . . . . ?
C26 C31 C32 N25 -69.57(13) . . . . ?
C30 C31 C32 C33 -11.59(15) . . . . ?
C26 C31 C32 C33 168.97(10) . . . . ?
C30 C31 C32 C40 -131.79(11) . . . . ?
C26 C31 C32 C40 48.78(14) . . . . ?
N25 C32 C33 C38 -104.91(12) . . . . ?
C31 C32 C33 C38 15.15(15) . . . . ?
C40 C32 C33 C38 134.44(11) . . . . ?
N25 C32 C33 C34 68.94(14) . . . . ?
C31 C32 C33 C34 -171.00(11) . . . . ?
C40 C32 C33 C34 -51.71(14) . . . . ?
C38 C33 C34 C35 0.52(19) . . . . ?
C32 C33 C34 C35 -173.58(12) . . . . ?
C33 C34 C35 C36 0.1(2) . . . . ?
C34 C35 C36 C37 -0.4(2) . . . . ?
C35 C36 C37 C38 0.06(19) . . . . ?
C34 C33 C38 O39 179.97(11) . . . . ?
C32 C33 C38 O39 -6.02(18) . . . . ?
C34 C33 C38 C37 -0.82(18) . . . . ?
C32 C33 C38 C37 173.19(11) . . . . ?
C36 C37 C38 O39 179.81(11) . . . . ?
C36 C37 C38 C33 0.54(19) . . . . ?
C31 C30 O39 C38 12.37(17) . . . . ?
C29 C30 O39 C38 -168.68(11) . . . . ?
C33 C38 O39 C30 -8.59(17) . . . . ?
C37 C38 O39 C30 172.16(11) . . . . ?
N25 C32 C40 C45 6.74(15) . . . . ?
C31 C32 C40 C45 -111.40(12) . . . . ?
C33 C32 C40 C45 128.58(12) . . . . ?
N25 C32 C40 C41 -175.29(10) . . . . ?
C31 C32 C40 C41 66.57(14) . . . . ?
C33 C32 C40 C41 -53.45(14) . . . . ?
C45 C40 C41 C42 -0.09(18) . . . . ?
C32 C40 C41 C42 -178.13(11) . . . . ?
C40 C41 C42 C43 -0.18(19) . . . . ?
C41 C42 C43 C44 0.18(19) . . . . ?
C41 C42 C43 Cl46 -179.94(10) . . . . ?
C42 C43 C44 C45 0.09(19) . . . . ?
Cl46 C43 C44 C45 -179.79(9) . . . . ?
C41 C40 C45 C44 0.37(18) . . . . ?
C32 C40 C45 C44 178.35(11) . . . . ?
C43 C44 C45 C40 -0.37(18) . . . . ?
C52 N47 C48 C49 -1.7(2) . . . . ?
N47 C48 C49 C50 1.5(2) . . . . ?
C48 C49 C50 C51 0.6(2) . . . . ?
C48 C49 C50 C53 -178.62(15) . . . . ?
C49 C50 C51 C52 -2.3(2) . . . . ?
C53 C50 C51 C52 176.96(14) . . . . ?
C48 N47 C52 C51 -0.1(2) . . . . ?
C50 C51 C52 N47 2.1(2) . . . . ?
C59 N54 C55 C56 0.2(2) . . . . ?
N54 C55 C56 C57 -2.7(2) . . . . ?
C55 C56 C57 C58 2.6(2) . . . . ?
C55 C56 C57 C60 -176.57(14) . . . . ?
C56 C57 C58 C59 -0.2(2) . . . . ?
C60 C57 C58 C59 178.96(15) . . . . ?
C55 N54 C59 C58 2.4(2) . . . . ?
C57 C58 C59 N54 -2.4(3) . . . . ?
