#------------------------------------------------------------------------------
#$Date: 2025-08-06 00:31:49 +0300 (Wed, 06 Aug 2025) $
#$Revision: 301558 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/06/7250668.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_7250668
loop_
_publ_author_name
'Tominaga, Masahide'
'Kamada, Ryusei'
'Hyodo, Tadashi'
'Yamaguchi, Kentaro'
_publ_section_title
;
 Co-crystals built from macrocycles with pyromellitic diimides and
 naphthalene derivatives: transformation of a binary co-crystal solvate to
 a solvate through solvent exchange
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              5003
_journal_page_last               5009
_journal_paper_doi               10.1039/D5CE00462D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_sum            'C103.5 H93.75 Br2 Cl9.75 N8 O16.75'
_chemical_formula_weight         2223.03
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-10-08 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                107.935(14)
_cell_angle_beta                 95.420(14)
_cell_angle_gamma                92.865(17)
_cell_formula_units_Z            1
_cell_length_a                   9.590(2)
_cell_length_b                   15.202(4)
_cell_length_c                   18.069(3)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.44
_cell_measurement_theta_min      3.61
_cell_volume                     2486.3(10)
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35907
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.101
_diffrn_reflns_theta_min         3.333
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    4.033
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_correction_T_min  0.8968
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.556
_refine_diff_density_min         -1.436
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     708
_refine_ls_number_reflns         10087
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0529
_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)+(0.0596P)²+3.6213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9339
_reflns_number_total             10087
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00462d2.cif
_cod_data_source_block           1e
_cod_depositor_comments
'Adding full bibliography for 7250664--7250669.cif.'
_cod_original_cell_volume        2486.5(10)
_cod_original_formula_sum        'C103.50 H93.75 Br2 Cl9.75 N8 O16.75'
_cod_database_code               7250668
_shelx_shelxl_version_number     2018/3
_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   0.499
_shelx_estimated_absorpt_t_max   0.739
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
C54 C 0.1991(9) 1.1399(8) 0.4007(6) 0.0539(14) Uani 0.375(3) 1 d D U P A -4
C55 C 0.2349(11) 1.1590(10) 0.4852(6) 0.0480(17) Uani 0.375(3) 1 d . U P A -4
H55A H 0.155208 1.137363 0.507096 0.072 Uiso 0.375(3) 1 calc R U P A -4
H55B H 0.256320 1.225860 0.510518 0.072 Uiso 0.375(3) 1 calc R U P A -4
H55C H 0.317153 1.126394 0.494501 0.072 Uiso 0.375(3) 1 calc R U P A -4
C56 C 0.1668(11) 1.0617(10) 0.3331(7) 0.0589(17) Uani 0.375(3) 1 d . U P A -4
H56A H 0.115050 1.012561 0.346608 0.088 Uiso 0.375(3) 1 calc R U P A -4
H56B H 0.254056 1.039109 0.312933 0.088 Uiso 0.375(3) 1 calc R U P A -4
H56C H 0.108893 1.079071 0.293029 0.088 Uiso 0.375(3) 1 calc R U P A -4
O9 O 0.2213(5) 1.2008(5) 0.3828(3) 0.0446(13) Uani 0.375(3) 1 d D U P A -4
C50 C 0.1451(6) 1.0744(4) 0.4316(3) 0.0493(14) Uani 0.625(3) 1 d . . P A -3
H50 H 0.187171 1.013376 0.419265 0.059 Uiso 0.625(3) 1 calc R U P A -3
Cl1 Cl 0.1359(5) 1.1083(3) 0.35104(17) 0.1369(16) Uani 0.625(3) 1 d . . P A -3
Cl2 Cl -0.0292(2) 1.05743(12) 0.44939(18) 0.1157(12) Uani 0.625(3) 1 d . . P A
-3
Cl3 Cl 0.23637(16) 1.14916(13) 0.51770(11) 0.0620(6) Uani 0.625(3) 1 d . . P A
-3
C52 C 0.6887(6) 0.1049(4) 0.0556(4) 0.0368(13) Uani 0.482(3) 1 d . . P B -2
H52 H 0.688356 0.123681 0.113660 0.044 Uiso 0.482(3) 1 calc R U P B -2
Cl7 Cl 0.53060(17) 0.04187(13) 0.00574(12) 0.0515(5) Uani 0.482(3) 1 d . . P B
-2
Cl8 Cl 0.8258(2) 0.04001(15) 0.02565(12) 0.0247(4) Uani 0.482(3) 1 d . . P B -2
Cl9 Cl 0.7127(7) 0.2130(5) 0.0187(3) 0.0551(11) Uani 0.482(3) 1 d . . P B -2
C51 C 0.7429(7) 0.0974(5) -0.0351(4) 0.0481(15) Uani 0.518(3) 1 d . . P B -1
H51 H 0.651814 0.060628 -0.059853 0.058 Uiso 0.518(3) 1 calc R U P B -1
Cl4 Cl 0.8225(6) 0.0440(4) 0.0218(4) 0.1133(19) Uani 0.518(3) 1 d . . P B -1
Cl5 Cl 0.6989(5) 0.2160(3) 0.0427(2) 0.0434(7) Uani 0.518(3) 1 d . . P B -1
Cl6 Cl 0.84822(17) 0.09536(12) -0.11019(9) 0.0492(5) Uani 0.518(3) 1 d . . P B
-1
C1 C 0.8580(3) 0.81519(17) 0.86656(14) 0.0257(5) Uani 1 1 d . . . . .
H1 H 0.897399 0.881373 0.883148 0.031 Uiso 1 1 calc R U . . .
C2 C 0.9487(2) 0.75481(17) 0.80816(14) 0.0239(5) Uani 1 1 d . . . . .
H2A H 1.046753 0.760958 0.833042 0.029 Uiso 1 1 calc R U . . .
H2B H 0.949126 0.776402 0.761779 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8904(2) 0.65240(17) 0.78235(13) 0.0213(5) Uani 1 1 d . . . . .
C4 C 0.8903(3) 0.61955(19) 0.85514(14) 0.0272(5) Uani 1 1 d . . . . .
H4A H 0.852596 0.553786 0.839175 0.033 Uiso 1 1 calc R U . . .
H4B H 0.987675 0.624363 0.880600 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7991(3) 0.6800(2) 0.91322(14) 0.0293(5) Uani 1 1 d . . . . .
H5 H 0.798902 0.658345 0.960184 0.035 Uiso 1 1 calc R U . . .
C6 C 0.8594(3) 0.7816(2) 0.93874(14) 0.0312(6) Uani 1 1 d . . . . .
H6A H 0.956874 0.787298 0.964262 0.037 Uiso 1 1 calc R U . . .
H6B H 0.802287 0.820520 0.977008 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7077(3) 0.80717(17) 0.82733(14) 0.0242(5) Uani 1 1 d . . . . .
H7A H 0.707191 0.829421 0.781267 0.029 Uiso 1 1 calc R U . . .
H7B H 0.649167 0.846405 0.864505 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7384(2) 0.64392(16) 0.74383(13) 0.0196(4) Uani 1 1 d . . . . .
H8A H 0.699626 0.578356 0.727760 0.024 Uiso 1 1 calc R U . . .
H8B H 0.737189 0.663395 0.696312 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6459(2) 0.70505(16) 0.80122(13) 0.0209(4) Uani 1 1 d . . . . .
C10 C 0.6482(3) 0.67180(18) 0.87367(14) 0.0258(5) Uani 1 1 d . . . . .
H10A H 0.589132 0.709814 0.911261 0.031 Uiso 1 1 calc R U . . .
H10B H 0.608695 0.606412 0.857695 0.031 Uiso 1 1 calc R U . . .
C11 C 0.9828(2) 0.58967(17) 0.72628(13) 0.0231(5) Uani 1 1 d . . . . .
H11A H 1.081341 0.601021 0.751056 0.028 Uiso 1 1 calc R U . . .
H11B H 0.951678 0.523967 0.718216 0.028 Uiso 1 1 calc R U . . .
C12 C 1.0678(2) 0.66669(17) 0.62995(13) 0.0219(5) Uani 1 1 d . . . . .
C13 C 1.0183(2) 0.65891(16) 0.54675(13) 0.0208(4) Uani 1 1 d . . . . .
C14 C 1.0687(2) 0.70752(17) 0.49972(14) 0.0226(5) Uani 1 1 d . . . . .
H14 H 1.146761 0.752731 0.517045 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9956(2) 0.68458(16) 0.42520(13) 0.0212(4) Uani 1 1 d . . . . .
C16 C 1.0161(2) 0.72408(17) 0.36028(14) 0.0239(5) Uani 1 1 d . . . . .
C17 C 0.8309(3) 0.61043(16) 0.31718(13) 0.0229(5) Uani 1 1 d . . . . .
C18 C 0.8827(2) 0.61708(16) 0.39955(13) 0.0215(5) Uani 1 1 d . . . . .
C19 C 0.8322(2) 0.56823(16) 0.44628(13) 0.0212(4) Uani 1 1 d . . . . .
H19 H 0.754667 0.522615 0.428871 0.025 Uiso 1 1 calc R U . . .
C20 C 0.9052(2) 0.59206(16) 0.52087(13) 0.0210(4) Uani 1 1 d . . . . .
C21 C 0.8816(2) 0.55368(16) 0.58592(13) 0.0210(5) Uani 1 1 d . . . . .
C22 C 0.8922(3) 0.69585(18) 0.22349(14) 0.0258(5) Uani 1 1 d . . . . .
H22A H 0.857131 0.636682 0.182696 0.031 Uiso 1 1 calc R U . . .
H22B H 0.985160 0.715174 0.211331 0.031 Uiso 1 1 calc R U . . .
C23 C 0.7903(3) 0.77001(17) 0.21905(14) 0.0240(5) Uani 1 1 d . . . . .
C24 C 0.8523(3) 0.86786(18) 0.26990(16) 0.0302(5) Uani 1 1 d . . . . .
H24A H 0.867875 0.870112 0.325427 0.036 Uiso 1 1 calc R U . . .
H24B H 0.944224 0.881807 0.253437 0.036 Uiso 1 1 calc R U . . .
C25 C 0.7519(3) 0.94119(19) 0.26170(18) 0.0339(6) Uani 1 1 d . . . . .
H25 H 0.793549 1.004294 0.294712 0.041 Uiso 1 1 calc R U . . .
C26 C 0.7281(3) 0.9378(2) 0.1756(2) 0.0432(7) Uani 1 1 d . . . . .
H26A H 0.663586 0.984801 0.170158 0.052 Uiso 1 1 calc R U . . .
H26B H 0.818581 0.952183 0.157965 0.052 Uiso 1 1 calc R U . . .
C27 C 0.6649(3) 0.8412(2) 0.12497(17) 0.0383(7) Uani 1 1 d . . . . .
H27 H 0.649599 0.839439 0.069000 0.046 Uiso 1 1 calc R U . . .
C28 C 0.7658(3) 0.7674(2) 0.13266(15) 0.0328(6) Uani 1 1 d . . . . .
H28A H 0.724842 0.705070 0.099581 0.039 Uiso 1 1 calc R U . . .
H28B H 0.856617 0.780075 0.114410 0.039 Uiso 1 1 calc R U . . .
C29 C 0.6477(2) 0.74949(16) 0.24519(13) 0.0211(4) Uani 1 1 d . . . . .
H29A H 0.661591 0.749471 0.300172 0.025 Uiso 1 1 calc R U . . .
H29B H 0.606307 0.687191 0.212200 0.025 Uiso 1 1 calc R U . . .
C30 C 0.6112(3) 0.91960(17) 0.28905(16) 0.0276(5) Uani 1 1 d . . . . .
H30A H 0.546158 0.966939 0.285076 0.033 Uiso 1 1 calc R U . . .
H30B H 0.626337 0.921694 0.344551 0.033 Uiso 1 1 calc R U . . .
C31 C 0.5459(3) 0.82295(17) 0.23826(13) 0.0227(5) Uani 1 1 d . . . . .
C32 C 0.5243(3) 0.8203(2) 0.15195(15) 0.0324(6) Uani 1 1 d . . . . .
H32A H 0.482077 0.758278 0.118816 0.039 Uiso 1 1 calc R U . . .
H32B H 0.458869 0.866804 0.146228 0.039 Uiso 1 1 calc R U . . .
C33 C 0.4017(3) 0.80260(17) 0.26219(14) 0.0240(5) Uani 1 1 d . . . . .
H33A H 0.344048 0.855019 0.262951 0.029 Uiso 1 1 calc R U . . .
H33B H 0.353854 0.746404 0.222255 0.029 Uiso 1 1 calc R U . . .
C34 C 0.3987(2) 0.85712(16) 0.40916(14) 0.0216(5) Uani 1 1 d . . . . .
C35 C 0.4113(2) 0.81041(15) 0.47092(13) 0.0199(4) Uani 1 1 d . . . . .
C36 C 0.4192(2) 0.84903(15) 0.55209(13) 0.0214(4) Uani 1 1 d . . . . .
H36 H 0.412710 0.913255 0.577390 0.026 Uiso 1 1 calc R U . . .
C37 C 0.4374(2) 0.78522(16) 0.59302(13) 0.0201(4) Uani 1 1 d . . . . .
C38 C 0.4535(2) 0.80050(16) 0.67968(14) 0.0218(5) Uani 1 1 d . . . . .
C39 C 0.4671(2) 0.64377(16) 0.61655(13) 0.0203(4) Uani 1 1 d . . . . .
C40 C 0.4464(2) 0.69057(15) 0.55528(13) 0.0193(4) Uani 1 1 d . . . . .
C41 C 0.4387(2) 0.65164(15) 0.47442(13) 0.0203(4) Uani 1 1 d . . . . .
H41 H 0.445569 0.587445 0.449233 0.024 Uiso 1 1 calc R U . . .
C42 C 0.4199(2) 0.71543(15) 0.43355(13) 0.0199(4) Uani 1 1 d . . . . .
C43 C 0.4108(2) 0.69928(16) 0.34737(14) 0.0213(4) Uani 1 1 d . . . . .
C44 C 0.4933(2) 0.69485(17) 0.76341(13) 0.0229(5) Uani 1 1 d . . . . .
H44A H 0.452765 0.630893 0.755110 0.027 Uiso 1 1 calc R U . . .
H44B H 0.438148 0.737877 0.800089 0.027 Uiso 1 1 calc R U . . .
C45 C 0.6238(3) 0.44980(17) -0.07371(14) 0.0244(5) Uani 1 1 d . . . . .
H45 H 0.629248 0.434331 -0.128400 0.029 Uiso 1 1 calc R U . . .
C46 C 0.7318(3) 0.43503(17) -0.02507(15) 0.0263(5) Uani 1 1 d . . . . .
C47 C 0.7281(3) 0.45764(18) 0.05661(15) 0.0279(5) Uani 1 1 d . . . . .
H47 H 0.805380 0.447298 0.088948 0.034 Uiso 1 1 calc R U . . .
C48 C 0.6124(3) 0.49445(17) 0.08866(14) 0.0261(5) Uani 1 1 d . . . . .
H48 H 0.609171 0.508997 0.143468 0.031 Uiso 1 1 calc R U . . .
C49 C 0.4969(2) 0.51129(16) 0.04100(13) 0.0210(5) Uani 1 1 d . . . . .
Br1 Br 0.89376(3) 0.38184(2) -0.06783(2) 0.04025(12) Uani 1 1 d . . . . .
N1 N 0.9774(2) 0.60512(14) 0.64984(11) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.9104(2) 0.67943(14) 0.29975(11) 0.0229(4) Uani 1 1 d . . . . .
N3 N 0.4786(2) 0.71381(13) 0.68844(11) 0.0196(4) Uani 1 1 d . . . . .
N4 N 0.4092(2) 0.78842(13) 0.33868(11) 0.0208(4) Uani 1 1 d . . . . .
O1 O 1.16678(17) 0.71437(13) 0.67199(10) 0.0283(4) Uani 1 1 d . . . . .
O2 O 1.10497(19) 0.78253(14) 0.35863(11) 0.0314(4) Uani 1 1 d . . . . .
O3 O 0.74150(19) 0.55591(12) 0.27285(10) 0.0278(4) Uani 1 1 d . . . . .
O4 O 0.80072(18) 0.48998(12) 0.58509(10) 0.0256(4) Uani 1 1 d . . . . .
O5 O 0.38393(19) 0.93892(12) 0.41724(10) 0.0265(4) Uani 1 1 d . . . . .
O6 O 0.4468(2) 0.87163(12) 0.73272(10) 0.0290(4) Uani 1 1 d . . . . .
O7 O 0.47079(18) 0.56108(11) 0.60760(10) 0.0252(4) Uani 1 1 d . . . . .
O8 O 0.40483(19) 0.62682(12) 0.29433(10) 0.0276(4) Uani 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 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
O9 C54 C56 109.0(11) . . ?
O9 C54 C55 112.0(11) . . ?
C56 C54 C55 137.9(11) . . ?
Cl1 C50 Cl3 118.0(4) . . ?
Cl1 C50 Cl2 105.8(3) . . ?
Cl3 C50 Cl2 107.5(3) . . ?
Cl8 C52 Cl7 108.8(3) . . ?
Cl8 C52 Cl9 105.3(4) . . ?
Cl7 C52 Cl9 106.9(4) . . ?
Cl4 C51 Cl6 107.8(5) . . ?
Cl4 C51 Cl5 102.3(4) . . ?
Cl6 C51 Cl5 122.6(4) . . ?
C7 C1 C6 110.0(2) . . ?
C7 C1 C2 109.40(19) . . ?
C6 C1 C2 109.1(2) . . ?
C1 C2 C3 110.3(2) . . ?
C8 C3 C2 109.03(19) . . ?
C8 C3 C11 111.10(18) . . ?
C2 C3 C11 111.39(19) . . ?
C8 C3 C4 108.69(19) . . ?
C2 C3 C4 109.11(19) . . ?
C11 C3 C4 107.45(19) . . ?
C5 C4 C3 109.6(2) . . ?
C10 C5 C6 109.4(2) . . ?
C10 C5 C4 109.5(2) . . ?
C6 C5 C4 109.5(2) . . ?
C5 C6 C1 109.4(2) . . ?
C1 C7 C9 109.9(2) . . ?
C3 C8 C9 110.68(18) . . ?
C44 C9 C10 108.42(19) . . ?
C44 C9 C7 111.26(19) . . ?
C10 C9 C7 108.80(19) . . ?
C44 C9 C8 110.69(18) . . ?
C10 C9 C8 108.08(19) . . ?
C7 C9 C8 109.51(19) . . ?
C5 C10 C9 110.4(2) . . ?
N1 C11 C3 113.28(19) . . ?
O1 C12 N1 125.8(2) . . ?
O1 C12 C13 128.3(2) . . ?
N1 C12 C13 105.93(19) . . ?
C20 C13 C14 122.6(2) . . ?
C20 C13 C12 108.0(2) . . ?
C14 C13 C12 129.4(2) . . ?
C13 C14 C15 114.5(2) . . ?
C14 C15 C18 122.5(2) . . ?
C14 C15 C16 129.6(2) . . ?
C18 C15 C16 107.9(2) . . ?
O2 C16 N2 125.6(2) . . ?
O2 C16 C15 128.4(2) . . ?
N2 C16 C15 106.0(2) . . ?
O3 C17 N2 125.8(2) . . ?
O3 C17 C18 128.2(2) . . ?
N2 C17 C18 106.1(2) . . ?
C19 C18 C15 123.1(2) . . ?
C19 C18 C17 129.0(2) . . ?
C15 C18 C17 107.9(2) . . ?
C18 C19 C20 114.0(2) . . ?
C13 C20 C19 123.3(2) . . ?
C13 C20 C21 108.0(2) . . ?
C19 C20 C21 128.8(2) . . ?
O4 C21 N1 125.4(2) . . ?
O4 C21 C20 128.6(2) . . ?
N1 C21 C20 105.99(19) . . ?
N2 C22 C23 114.49(19) . . ?
C29 C23 C24 108.9(2) . . ?
C29 C23 C22 111.5(2) . . ?
C24 C23 C22 111.4(2) . . ?
C29 C23 C28 108.3(2) . . ?
C24 C23 C28 109.1(2) . . ?
C22 C23 C28 107.49(19) . . ?
C25 C24 C23 110.5(2) . . ?
C30 C25 C26 109.5(2) . . ?
C30 C25 C24 108.8(2) . . ?
C26 C25 C24 109.5(2) . . ?
C27 C26 C25 109.8(2) . . ?
C32 C27 C26 109.2(2) . . ?
C32 C27 C28 109.5(2) . . ?
C26 C27 C28 110.0(3) . . ?
C23 C28 C27 109.6(2) . . ?
C23 C29 C31 110.77(19) . . ?
C25 C30 C31 110.0(2) . . ?
C33 C31 C30 110.5(2) . . ?
C33 C31 C32 107.7(2) . . ?
C30 C31 C32 109.1(2) . . ?
C33 C31 C29 111.71(19) . . ?
C30 C31 C29 109.3(2) . . ?
C32 C31 C29 108.38(19) . . ?
C27 C32 C31 110.1(2) . . ?
N4 C33 C31 113.47(19) . . ?
O5 C34 N4 125.8(2) . . ?
O5 C34 C35 128.2(2) . . ?
N4 C34 C35 105.99(19) . . ?
C36 C35 C42 122.8(2) . . ?
C36 C35 C34 129.3(2) . . ?
C42 C35 C34 107.8(2) . . ?
C35 C36 C37 114.3(2) . . ?
C36 C37 C40 122.5(2) . . ?
C36 C37 C38 129.8(2) . . ?
C40 C37 C38 107.67(19) . . ?
O6 C38 N3 125.5(2) . . ?
O6 C38 C37 128.7(2) . . ?
N3 C38 C37 105.75(19) . . ?
O7 C39 N3 125.5(2) . . ?
O7 C39 C40 128.3(2) . . ?
N3 C39 C40 106.22(19) . . ?
C41 C40 C37 123.5(2) . . ?
C41 C40 C39 128.5(2) . . ?
C37 C40 C39 108.06(19) . . ?
C40 C41 C42 113.9(2) . . ?
C41 C42 C35 122.9(2) . . ?
C41 C42 C43 128.8(2) . . ?
C35 C42 C43 108.3(2) . . ?
O8 C43 N4 125.5(2) . . ?
O8 C43 C42 129.3(2) . . ?
N4 C43 C42 105.21(19) . . ?
N3 C44 C9 113.76(19) . . ?
C46 C45 C49 118.8(2) . 2_665 ?
C45 C46 C47 122.3(2) . . ?
C45 C46 Br1 119.51(19) . . ?
C47 C46 Br1 118.21(19) . . ?
C48 C47 C46 119.5(2) . . ?
C47 C48 C49 120.8(2) . . ?
C48 C49 C45 121.3(2) . 2_665 ?
C48 C49 C49 118.9(3) . 2_665 ?
C45 C49 C49 119.7(3) 2_665 2_665 ?
C12 N1 C21 111.85(19) . . ?
C12 N1 C11 125.90(19) . . ?
C21 N1 C11 122.2(2) . . ?
C16 N2 C17 111.84(19) . . ?
C16 N2 C22 124.7(2) . . ?
C17 N2 C22 123.2(2) . . ?
C39 N3 C38 111.97(19) . . ?
C39 N3 C44 122.67(19) . . ?
C38 N3 C44 124.71(19) . . ?
C34 N4 C43 112.24(19) . . ?
C34 N4 C33 125.09(19) . . ?
C43 N4 C33 122.25(19) . . ?
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
C54 O9 1.088(11) . ?
C54 C56 1.414(17) . ?
C54 C55 1.467(14) . ?
C50 Cl1 1.683(6) . ?
C50 Cl3 1.742(6) . ?
C50 Cl2 1.753(7) . ?
C52 Cl8 1.712(7) . ?
C52 Cl7 1.759(6) . ?
C52 Cl9 1.965(9) . ?
C51 Cl4 1.652(9) . ?
C51 Cl6 1.760(7) . ?
C51 Cl5 2.007(9) . ?
C1 C7 1.527(3) . ?
C1 C6 1.539(3) . ?
C1 C2 1.539(3) . ?
C2 C3 1.540(3) . ?
C3 C8 1.536(3) . ?
C3 C11 1.543(3) . ?
C3 C4 1.544(3) . ?
C4 C5 1.539(4) . ?
C5 C10 1.534(4) . ?
C5 C6 1.535(4) . ?
C7 C9 1.545(3) . ?
C8 C9 1.546(3) . ?
C9 C44 1.535(3) . ?
C9 C10 1.540(3) . ?
C11 N1 1.467(3) . ?
C12 O1 1.208(3) . ?
C12 N1 1.393(3) . ?
C12 C13 1.500(3) . ?
C13 C20 1.389(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.391(3) . ?
C15 C18 1.393(3) . ?
C15 C16 1.497(3) . ?
C16 O2 1.209(3) . ?
C16 N2 1.396(3) . ?
C17 O3 1.206(3) . ?
C17 N2 1.396(3) . ?
C17 C18 1.495(3) . ?
C18 C19 1.388(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.494(3) . ?
C21 O4 1.206(3) . ?
C21 N1 1.400(3) . ?
C22 N2 1.471(3) . ?
C22 C23 1.544(3) . ?
C23 C29 1.536(3) . ?
C23 C24 1.542(4) . ?
C23 C28 1.544(3) . ?
C24 C25 1.541(4) . ?
C25 C30 1.534(4) . ?
C25 C26 1.534(4) . ?
C26 C27 1.529(5) . ?
C27 C32 1.528(4) . ?
C27 C28 1.547(4) . ?
C29 C31 1.545(3) . ?
C30 C31 1.537(3) . ?
C31 C33 1.532(3) . ?
C31 C32 1.542(3) . ?
C33 N4 1.459(3) . ?
C34 O5 1.224(3) . ?
C34 N4 1.392(3) . ?
C34 C35 1.495(3) . ?
C35 C36 1.395(3) . ?
C35 C42 1.403(3) . ?
C36 C37 1.397(3) . ?
C37 C40 1.401(3) . ?
C37 C38 1.502(3) . ?
C38 O6 1.213(3) . ?
C38 N3 1.405(3) . ?
C39 O7 1.220(3) . ?
C39 N3 1.394(3) . ?
C39 C40 1.493(3) . ?
C40 C41 1.390(3) . ?
C41 C42 1.397(3) . ?
C42 C43 1.493(3) . ?
C43 O8 1.212(3) . ?
C43 N4 1.412(3) . ?
C44 N3 1.465(3) . ?
C45 C46 1.367(4) . ?
C45 C49 1.422(3) 2_665 ?
C46 C47 1.413(4) . ?
C46 Br1 1.905(3) . ?
C47 C48 1.364(4) . ?
C48 C49 1.421(3) . ?
C49 C49 1.422(4) 2_665 ?
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
C7 C1 C2 C3 -60.5(3) . . . . ?
C6 C1 C2 C3 59.8(2) . . . . ?
C1 C2 C3 C8 59.3(2) . . . . ?
C1 C2 C3 C11 -177.74(18) . . . . ?
C1 C2 C3 C4 -59.3(2) . . . . ?
C8 C3 C4 C5 -59.6(3) . . . . ?
C2 C3 C4 C5 59.2(3) . . . . ?
C11 C3 C4 C5 -179.9(2) . . . . ?
C3 C4 C5 C10 59.7(3) . . . . ?
C3 C4 C5 C6 -60.3(3) . . . . ?
C10 C5 C6 C1 -59.4(3) . . . . ?
C4 C5 C6 C1 60.7(3) . . . . ?
C7 C1 C6 C5 59.8(3) . . . . ?
C2 C1 C6 C5 -60.2(3) . . . . ?
C6 C1 C7 C9 -59.9(3) . . . . ?
C2 C1 C7 C9 59.9(3) . . . . ?
C2 C3 C8 C9 -58.3(2) . . . . ?
C11 C3 C8 C9 178.52(18) . . . . ?
C4 C3 C8 C9 60.5(2) . . . . ?
C1 C7 C9 C44 178.51(19) . . . . ?
C1 C7 C9 C10 59.1(2) . . . . ?
C1 C7 C9 C8 -58.8(2) . . . . ?
C3 C8 C9 C44 -178.69(18) . . . . ?
C3 C8 C9 C10 -60.1(2) . . . . ?
C3 C8 C9 C7 58.3(2) . . . . ?
C6 C5 C10 C9 59.9(3) . . . . ?
C4 C5 C10 C9 -60.2(3) . . . . ?
C44 C9 C10 C5 179.6(2) . . . . ?
C7 C9 C10 C5 -59.3(3) . . . . ?
C8 C9 C10 C5 59.5(3) . . . . ?
C8 C3 C11 N1 53.6(3) . . . . ?
C2 C3 C11 N1 -68.1(2) . . . . ?
C4 C3 C11 N1 172.39(19) . . . . ?
O1 C12 C13 C20 176.9(2) . . . . ?
N1 C12 C13 C20 -1.7(2) . . . . ?
O1 C12 C13 C14 -3.9(4) . . . . ?
N1 C12 C13 C14 177.5(2) . . . . ?
C20 C13 C14 C15 0.8(3) . . . . ?
C12 C13 C14 C15 -178.4(2) . . . . ?
C13 C14 C15 C18 -1.1(3) . . . . ?
C13 C14 C15 C16 177.8(2) . . . . ?
C14 C15 C16 O2 2.9(4) . . . . ?
C18 C15 C16 O2 -178.1(2) . . . . ?
C14 C15 C16 N2 -177.2(2) . . . . ?
C18 C15 C16 N2 1.8(3) . . . . ?
C14 C15 C18 C19 1.1(4) . . . . ?
C16 C15 C18 C19 -178.0(2) . . . . ?
C14 C15 C18 C17 -179.6(2) . . . . ?
C16 C15 C18 C17 1.3(2) . . . . ?
O3 C17 C18 C19 -6.4(4) . . . . ?
N2 C17 C18 C19 175.3(2) . . . . ?
O3 C17 C18 C15 174.4(2) . . . . ?
N2 C17 C18 C15 -3.9(2) . . . . ?
C15 C18 C19 C20 -0.6(3) . . . . ?
C17 C18 C19 C20 -179.7(2) . . . . ?
C14 C13 C20 C19 -0.4(4) . . . . ?
C12 C13 C20 C19 178.9(2) . . . . ?
C14 C13 C20 C21 179.3(2) . . . . ?
C12 C13 C20 C21 -1.4(2) . . . . ?
C18 C19 C20 C13 0.2(3) . . . . ?
C18 C19 C20 C21 -179.3(2) . . . . ?
C13 C20 C21 O4 -174.0(2) . . . . ?
C19 C20 C21 O4 5.6(4) . . . . ?
C13 C20 C21 N1 4.0(2) . . . . ?
C19 C20 C21 N1 -176.4(2) . . . . ?
N2 C22 C23 C29 -52.8(3) . . . . ?
N2 C22 C23 C24 69.2(3) . . . . ?
N2 C22 C23 C28 -171.4(2) . . . . ?
C29 C23 C24 C25 -59.1(3) . . . . ?
C22 C23 C24 C25 177.5(2) . . . . ?
C28 C23 C24 C25 59.0(3) . . . . ?
C23 C24 C25 C30 60.4(3) . . . . ?
C23 C24 C25 C26 -59.3(3) . . . . ?
C30 C25 C26 C27 -59.8(3) . . . . ?
C24 C25 C26 C27 59.4(3) . . . . ?
C25 C26 C27 C32 60.2(3) . . . . ?
C25 C26 C27 C28 -59.9(3) . . . . ?
C29 C23 C28 C27 59.8(3) . . . . ?
C24 C23 C28 C27 -58.7(3) . . . . ?
C22 C23 C28 C27 -179.6(2) . . . . ?
C32 C27 C28 C23 -60.3(3) . . . . ?
C26 C27 C28 C23 59.7(3) . . . . ?
C24 C23 C29 C31 58.2(2) . . . . ?
C22 C23 C29 C31 -178.49(19) . . . . ?
C28 C23 C29 C31 -60.4(3) . . . . ?
C26 C25 C30 C31 59.2(3) . . . . ?
C24 C25 C30 C31 -60.4(3) . . . . ?
C25 C30 C31 C33 -177.0(2) . . . . ?
C25 C30 C31 C32 -58.7(3) . . . . ?
C25 C30 C31 C29 59.6(3) . . . . ?
C23 C29 C31 C33 178.65(19) . . . . ?
C23 C29 C31 C30 -58.7(2) . . . . ?
C23 C29 C31 C32 60.1(3) . . . . ?
C26 C27 C32 C31 -60.2(3) . . . . ?
C28 C27 C32 C31 60.3(3) . . . . ?
C33 C31 C32 C27 179.4(2) . . . . ?
C30 C31 C32 C27 59.4(3) . . . . ?
C29 C31 C32 C27 -59.5(3) . . . . ?
C30 C31 C33 N4 -70.0(3) . . . . ?
C32 C31 C33 N4 170.8(2) . . . . ?
C29 C31 C33 N4 51.9(3) . . . . ?
O5 C34 C35 C36 -5.0(4) . . . . ?
N4 C34 C35 C36 174.2(2) . . . . ?
O5 C34 C35 C42 177.2(2) . . . . ?
N4 C34 C35 C42 -3.5(2) . . . . ?
C42 C35 C36 C37 0.4(3) . . . . ?
C34 C35 C36 C37 -177.0(2) . . . . ?
C35 C36 C37 C40 -0.2(3) . . . . ?
C35 C36 C37 C38 178.5(2) . . . . ?
C36 C37 C38 O6 4.2(4) . . . . ?
C40 C37 C38 O6 -176.9(2) . . . . ?
C36 C37 C38 N3 -175.8(2) . . . . ?
C40 C37 C38 N3 3.0(2) . . . . ?
C36 C37 C40 C41 0.2(4) . . . . ?
C38 C37 C40 C41 -178.7(2) . . . . ?
C36 C37 C40 C39 179.4(2) . . . . ?
C38 C37 C40 C39 0.5(2) . . . . ?
O7 C39 C40 C41 -6.0(4) . . . . ?
N3 C39 C40 C41 175.3(2) . . . . ?
O7 C39 C40 C37 174.9(2) . . . . ?
N3 C39 C40 C37 -3.8(2) . . . . ?
C37 C40 C41 C42 -0.5(3) . . . . ?
C39 C40 C41 C42 -179.4(2) . . . . ?
C40 C41 C42 C35 0.7(3) . . . . ?
C40 C41 C42 C43 178.3(2) . . . . ?
C36 C35 C42 C41 -0.7(4) . . . . ?
C34 C35 C42 C41 177.2(2) . . . . ?
C36 C35 C42 C43 -178.8(2) . . . . ?
C34 C35 C42 C43 -0.9(2) . . . . ?
C41 C42 C43 O8 7.6(4) . . . . ?
C35 C42 C43 O8 -174.6(2) . . . . ?
C41 C42 C43 N4 -173.0(2) . . . . ?
C35 C42 C43 N4 4.9(2) . . . . ?
C10 C9 C44 N3 -173.12(19) . . . . ?
C7 C9 C44 N3 67.3(2) . . . . ?
C8 C9 C44 N3 -54.7(3) . . . . ?
C49 C45 C46 C47 -0.4(4) 2_665 . . . ?
C49 C45 C46 Br1 179.40(17) 2_665 . . . ?
C45 C46 C47 C48 0.8(4) . . . . ?
Br1 C46 C47 C48 -179.0(2) . . . . ?
C46 C47 C48 C49 -0.8(4) . . . . ?
C47 C48 C49 C45 -179.6(2) . . . 2_665 ?
C47 C48 C49 C49 0.3(4) . . . 2_665 ?
O1 C12 N1 C21 -174.2(2) . . . . ?
C13 C12 N1 C21 4.5(3) . . . . ?
O1 C12 N1 C11 2.5(4) . . . . ?
C13 C12 N1 C11 -178.9(2) . . . . ?
O4 C21 N1 C12 172.8(2) . . . . ?
C20 C21 N1 C12 -5.3(3) . . . . ?
O4 C21 N1 C11 -4.0(4) . . . . ?
C20 C21 N1 C11 177.88(19) . . . . ?
C3 C11 N1 C12 91.5(3) . . . . ?
C3 C11 N1 C21 -92.2(3) . . . . ?
O2 C16 N2 C17 175.4(2) . . . . ?
C15 C16 N2 C17 -4.5(3) . . . . ?
O2 C16 N2 C22 1.0(4) . . . . ?
C15 C16 N2 C22 -178.9(2) . . . . ?
O3 C17 N2 C16 -173.1(2) . . . . ?
C18 C17 N2 C16 5.3(3) . . . . ?
O3 C17 N2 C22 1.4(4) . . . . ?
C18 C17 N2 C22 179.8(2) . . . . ?
C23 C22 N2 C16 -92.9(3) . . . . ?
C23 C22 N2 C17 93.2(3) . . . . ?
O7 C39 N3 C38 -172.8(2) . . . . ?
C40 C39 N3 C38 5.9(2) . . . . ?
O7 C39 N3 C44 -1.7(3) . . . . ?
C40 C39 N3 C44 177.01(19) . . . . ?
O6 C38 N3 C39 174.3(2) . . . . ?
C37 C38 N3 C39 -5.6(2) . . . . ?
O6 C38 N3 C44 3.4(4) . . . . ?
C37 C38 N3 C44 -176.50(19) . . . . ?
C9 C44 N3 C39 96.9(2) . . . . ?
C9 C44 N3 C38 -93.1(3) . . . . ?
O5 C34 N4 C43 -173.8(2) . . . . ?
C35 C34 N4 C43 6.9(2) . . . . ?
O5 C34 N4 C33 -1.1(4) . . . . ?
C35 C34 N4 C33 179.7(2) . . . . ?
O8 C43 N4 C34 172.1(2) . . . . ?
C42 C43 N4 C34 -7.4(2) . . . . ?
O8 C43 N4 C33 -0.9(4) . . . . ?
C42 C43 N4 C33 179.62(19) . . . . ?
C31 C33 N4 C34 93.6(3) . . . . ?
C31 C33 N4 C43 -94.3(3) . . . . ?
