#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:02:59 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281394 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/80/1568057.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_1568057
loop_
_publ_author_name
'Tajima, Keita'
'Matsuo, Kyohei'
'Yamada, Hiroko'
'Fukui, Norihito'
'Shinokubo, Hiroshi'
_publ_section_title
;
 Diazazethrene bisimide: a strongly electron-accepting π-system
 synthesized via the incorporation of both imide substituents and
 imine-type nitrogen atoms into zethrene.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              635
_journal_page_last               642
_journal_paper_doi               10.1039/d2sc05992d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C50 H34 Cl2 N4 O4'
_chemical_formula_weight         825.71
_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
;
2022-10-05 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                102.210(5)
_cell_angle_beta                 97.445(4)
_cell_angle_gamma                96.128(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0994(3)
_cell_length_b                   11.7159(8)
_cell_length_c                   21.0793(12)
_cell_measurement_reflns_used    3643
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      29.8200
_cell_measurement_theta_min      1.9940
_cell_volume                     1919.86(19)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13996
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.796
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.963
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         7359
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0840
_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)+(0.1264P)²+2.1608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2193
_refine_ls_wR_factor_ref         0.2513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4918
_reflns_number_total             7359
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05992d2.cif
_cod_data_source_block           Mes
_cod_depositor_comments
'Adding full bibliography for 1568056--1568059.cif.'
_cod_database_code               1568057
_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.
;
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
C1 C 0.8247(5) 0.7825(3) 0.66894(19) 0.0337(9) Uani 1 1 d . . . . .
C2 C 0.8088(5) 0.8516(4) 0.7296(2) 0.0395(10) Uani 1 1 d . . . . .
H1 H 0.862528 0.928886 0.742279 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7144(5) 0.8072(4) 0.7713(2) 0.0423(10) Uani 1 1 d . . . . .
H2 H 0.702707 0.855520 0.811087 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6379(5) 0.6927(4) 0.7545(2) 0.0372(9) Uani 1 1 d . . . . .
C5 C 0.5648(5) 0.5036(4) 0.6721(2) 0.0362(9) Uani 1 1 d . . . . .
C6 C 0.5711(5) 0.4375(4) 0.6107(2) 0.0423(10) Uani 1 1 d . . . . .
H3 H 0.515081 0.360787 0.597794 0.051 Uiso 1 1 calc R U . . .
C7 C 0.6612(5) 0.4840(4) 0.5668(2) 0.0418(10) Uani 1 1 d . . . . .
H4 H 0.662757 0.438755 0.524946 0.050 Uiso 1 1 calc R U . . .
C8 C 0.7470(5) 0.5970(3) 0.5862(2) 0.0345(9) Uani 1 1 d . . . . .
C9 C 0.7385(5) 0.6669(4) 0.64803(19) 0.0338(9) Uani 1 1 d . . . . .
C10 C 0.6441(5) 0.6198(3) 0.6914(2) 0.0353(9) Uani 1 1 d . . . . .
C11 C 0.9382(5) 0.8278(3) 0.62801(18) 0.0312(8) Uani 1 1 d . . . . .
C12 C 0.8508(5) 0.6429(3) 0.5420(2) 0.0356(9) Uani 1 1 d . . . . .
C13 C 0.4795(4) 0.4567(3) 0.72129(19) 0.0311(8) Uani 1 1 d . . . . .
C14 C 0.1360(4) 0.2154(3) 0.83446(18) 0.0313(9) Uani 1 1 d . . . . .
C15 C 0.1514(5) 0.1468(4) 0.77369(19) 0.0363(9) Uani 1 1 d . . . . .
H5 H 0.095506 0.070055 0.760265 0.044 Uiso 1 1 calc R U . . .
C16 C 0.2494(5) 0.1915(4) 0.7328(2) 0.0381(9) Uani 1 1 d . . . . .
H6 H 0.262265 0.143541 0.693054 0.046 Uiso 1 1 calc R U . . .
C17 C 0.3270(5) 0.3054(4) 0.75044(19) 0.0362(9) Uani 1 1 d . . . . .
C18 C 0.3979(5) 0.4940(4) 0.8330(2) 0.0348(9) Uani 1 1 d . . . . .
C19 C 0.3900(5) 0.5601(4) 0.8946(2) 0.0449(11) Uani 1 1 d . . . . .
H7 H 0.446278 0.636726 0.907812 0.054 Uiso 1 1 calc R U . . .
C20 C 0.2988(5) 0.5140(4) 0.9378(2) 0.0423(10) Uani 1 1 d . . . . .
H8 H 0.295363 0.559442 0.979364 0.051 Uiso 1 1 calc R U . . .
C21 C 0.2135(5) 0.3999(3) 0.9180(2) 0.0342(9) Uani 1 1 d . . . . .
C22 C 0.2228(5) 0.3309(3) 0.85614(19) 0.0328(9) Uani 1 1 d . . . . .
C23 C 0.3190(5) 0.3779(4) 0.8134(2) 0.0364(9) Uani 1 1 d . . . . .
C24 C 0.0219(5) 0.1694(3) 0.87466(19) 0.0320(9) Uani 1 1 d . . . . .
C25 C 0.1123(5) 0.3530(3) 0.9625(2) 0.0323(9) Uani 1 1 d . . . . .
C26 C 0.4855(5) 0.5412(3) 0.7839(2) 0.0360(9) Uani 1 1 d . . . . .
C27 C 1.0571(4) 0.7967(3) 0.52578(17) 0.0284(8) Uani 1 1 d . . . . .
C28 C 0.9898(4) 0.8404(3) 0.47339(18) 0.0273(8) Uani 1 1 d . . . . .
C29 C 1.0972(4) 0.8762(3) 0.43298(18) 0.0308(8) Uani 1 1 d . . . . .
H9 H 1.053599 0.905726 0.397698 0.037 Uiso 1 1 calc R U . . .
C30 C 1.2675(4) 0.8691(3) 0.44374(19) 0.0324(9) Uani 1 1 d . . . . .
C31 C 1.3305(5) 0.8253(3) 0.49686(19) 0.0367(9) Uani 1 1 d . . . . .
H10 H 1.444871 0.820328 0.504716 0.044 Uiso 1 1 calc R U . . .
C32 C 1.2273(5) 0.7886(3) 0.53860(18) 0.0334(9) Uani 1 1 d . . . . .
C33 C 0.8062(4) 0.8489(3) 0.45842(19) 0.0334(9) Uani 1 1 d . . . . .
H11 H 0.785789 0.881284 0.420384 0.050 Uiso 1 1 calc R U . . .
H12 H 0.742786 0.771746 0.449995 0.050 Uiso 1 1 calc R U . . .
H13 H 0.772280 0.899132 0.495271 0.050 Uiso 1 1 calc R U . . .
C34 C 1.3816(5) 0.9075(4) 0.3987(2) 0.0394(10) Uani 1 1 d . . . . .
H14 H 1.494771 0.896484 0.413427 0.059 Uiso 1 1 calc R U . . .
H15 H 1.345101 0.861097 0.354771 0.059 Uiso 1 1 calc R U . . .
H16 H 1.377483 0.989240 0.399210 0.059 Uiso 1 1 calc R U . . .
C35 C 1.2972(5) 0.7401(4) 0.5953(2) 0.0482(11) Uani 1 1 d . . . . .
H17 H 1.416306 0.741139 0.596657 0.072 Uiso 1 1 calc R U . . .
H18 H 1.275483 0.787694 0.635579 0.072 Uiso 1 1 calc R U . . .
H19 H 1.244602 0.660569 0.589969 0.072 Uiso 1 1 calc R U . . .
C36 C -0.0847(4) 0.1950(3) 0.97966(18) 0.0278(8) Uani 1 1 d . . . . .
C37 C -0.0035(4) 0.1564(3) 1.03201(18) 0.0283(8) Uani 1 1 d . . . . .
C38 C -0.1010(4) 0.1193(3) 1.07539(18) 0.0300(8) Uani 1 1 d . . . . .
H20 H -0.048864 0.094480 1.111069 0.036 Uiso 1 1 calc R U . . .
C39 C -0.2738(5) 0.1182(3) 1.06693(19) 0.0326(9) Uani 1 1 d . . . . .
C40 C -0.3503(5) 0.1535(3) 1.01312(19) 0.0335(9) Uani 1 1 d . . . . .
H21 H -0.466571 0.150575 1.006266 0.040 Uiso 1 1 calc R U . . .
C41 C -0.2580(5) 0.1932(3) 0.96913(18) 0.0317(8) Uani 1 1 d . . . . .
C42 C 0.1829(4) 0.1545(3) 1.04281(19) 0.0328(9) Uani 1 1 d . . . . .
H22 H 0.231417 0.182618 1.008831 0.049 Uiso 1 1 calc R U . . .
H23 H 0.231423 0.204308 1.084812 0.049 Uiso 1 1 calc R U . . .
H24 H 0.204960 0.075244 1.041688 0.049 Uiso 1 1 calc R U . . .
C43 C -0.3759(5) 0.0803(4) 1.1157(2) 0.0415(10) Uani 1 1 d . . . . .
H25 H -0.302895 0.058860 1.149605 0.062 Uiso 1 1 calc R U . . .
H26 H -0.431984 0.144126 1.134872 0.062 Uiso 1 1 calc R U . . .
H27 H -0.457890 0.013669 1.093652 0.062 Uiso 1 1 calc R U . . .
C44 C -0.3448(5) 0.2320(4) 0.9113(2) 0.0460(11) Uani 1 1 d . . . . .
H28 H -0.262763 0.256620 0.886164 0.069 Uiso 1 1 calc R U . . .
H29 H -0.423219 0.167571 0.884214 0.069 Uiso 1 1 calc R U . . .
H30 H -0.403806 0.296694 0.926812 0.069 Uiso 1 1 calc R U . . .
C45 C 1.0142(4) 0.5436(3) 0.28677(13) 0.0294(12) Uani 0.823(3) 1 d G U P A 1
C46 C 0.9792(4) 0.4419(3) 0.23669(17) 0.0294(12) Uani 0.823(3) 1 d G U P A 1
C47 C 1.0432(4) 0.4389(2) 0.17836(14) 0.0342(12) Uani 0.823(3) 1 d G U P A 1
H31 H 1.019773 0.370894 0.144854 0.041 Uiso 0.823(3) 1 calc R U P A 1
C48 C 1.1421(4) 0.5376(3) 0.17010(13) 0.0355(11) Uani 0.823(3) 1 d G U P A 1
H32 H 1.184874 0.535581 0.131070 0.043 Uiso 0.823(3) 1 calc R U P A 1
C49 C 1.1771(4) 0.6393(2) 0.22018(16) 0.0344(12) Uani 0.823(3) 1 d G U P A 1
H33 H 1.243255 0.705286 0.214649 0.041 Uiso 0.823(3) 1 calc R U P A 1
C50 C 1.1131(4) 0.6423(3) 0.27851(14) 0.0314(11) Uani 0.823(3) 1 d G U P A 1
H34 H 1.136535 0.710306 0.312014 0.038 Uiso 0.823(3) 1 calc R U P A 1
N1 N 0.5533(4) 0.6489(3) 0.80006(17) 0.0395(8) Uani 1 1 d . . . . .
N2 N 0.4140(4) 0.3488(3) 0.70526(17) 0.0388(8) Uani 1 1 d . . . . .
N3 N 0.9457(4) 0.7547(3) 0.56690(15) 0.0307(7) Uani 1 1 d . . . . .
N4 N 0.0172(4) 0.2412(3) 0.93674(15) 0.0296(7) Uani 1 1 d . . . . .
O1 O 1.0254(3) 0.9238(2) 0.64601(13) 0.0385(7) Uani 1 1 d . . . . .
O2 O 0.8581(4) 0.5882(2) 0.48689(14) 0.0458(8) Uani 1 1 d . . . . .
O3 O -0.0670(3) 0.0743(2) 0.85602(13) 0.0361(7) Uani 1 1 d . . . . .
O4 O 0.1071(4) 0.4060(2) 1.01805(14) 0.0425(7) Uani 1 1 d . . . . .
Cl1 Cl 0.93852(15) 0.55079(11) 0.35963(6) 0.0352(3) Uani 0.823(3) 1 d . U P A 1
Cl2 Cl 0.85691(16) 0.31849(11) 0.24541(7) 0.0391(4) Uani 0.823(3) 1 d . U P A 1
Cl3 Cl 1.0739(10) 0.4596(8) 0.1424(4) 0.063(2) Uani 0.177(3) 1 d . U P A 2
Cl4 Cl 1.1618(12) 0.6867(8) 0.2559(5) 0.067(3) Uani 0.177(3) 1 d . U P A 2
C55 C 0.842(2) 0.3647(14) 0.2800(10) 0.053(6) Uani 0.177(3) 1 d G U P A 2
H35 H 0.776575 0.297535 0.284740 0.064 Uiso 0.177(3) 1 calc R U P A 2
C54 C 0.876(2) 0.4645(17) 0.3313(8) 0.062(6) Uani 0.177(3) 1 d G U P A 2
H36 H 0.834572 0.464190 0.370328 0.074 Uiso 0.177(3) 1 calc R U P A 2
C52 C 0.974(3) 0.5649(14) 0.3243(8) 0.054(6) Uani 0.177(3) 1 d G U P A 2
H37 H 0.997061 0.631679 0.358586 0.065 Uiso 0.177(3) 1 calc R U P A 2
C56 C 1.036(2) 0.5654(15) 0.2660(10) 0.037(6) Uani 0.177(3) 1 d G U P A 2
C53 C 1.002(3) 0.4655(19) 0.2147(8) 0.037(6) Uani 0.177(3) 1 d G U P A 2
C51 C 0.904(3) 0.3652(15) 0.2217(8) 0.060(6) Uani 0.177(3) 1 d G U P A 2
H38 H 0.881071 0.298371 0.187408 0.072 Uiso 0.177(3) 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'
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 C9 120.0(4) . . ?
C2 C1 C11 120.1(4) . . ?
C9 C1 C11 119.8(4) . . ?
C3 C2 C1 121.1(4) . . ?
C4 C3 C2 120.5(4) . . ?
C3 C4 N1 118.7(4) . . ?
C3 C4 C10 120.4(4) . . ?
N1 C4 C10 120.9(4) . . ?
C6 C5 C10 120.1(4) . . ?
C6 C5 C13 123.1(4) . . ?
C10 C5 C13 116.9(4) . . ?
C5 C6 C7 121.0(4) . . ?
C8 C7 C6 119.6(4) . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 C12 119.7(4) . . ?
C9 C8 C12 120.2(3) . . ?
C8 C9 C1 121.2(4) . . ?
C8 C9 C10 119.6(4) . . ?
C1 C9 C10 119.1(4) . . ?
C5 C10 C9 119.4(4) . . ?
C5 C10 C4 122.0(4) . . ?
C9 C10 C4 118.6(4) . . ?
O1 C11 N3 120.2(3) . . ?
O1 C11 C1 122.5(4) . . ?
N3 C11 C1 117.2(3) . . ?
O2 C12 N3 120.1(4) . . ?
O2 C12 C8 123.2(4) . . ?
N3 C12 C8 116.7(3) . . ?
N2 C13 C26 127.8(4) . . ?
N2 C13 C5 117.3(4) . . ?
C26 C13 C5 114.9(3) . . ?
C15 C14 C22 120.4(4) . . ?
C15 C14 C24 119.6(4) . . ?
C22 C14 C24 119.9(3) . . ?
C16 C15 C14 120.6(4) . . ?
C17 C16 C15 120.6(4) . . ?
C16 C17 N2 118.2(4) . . ?
C16 C17 C23 120.5(4) . . ?
N2 C17 C23 121.3(4) . . ?
C19 C18 C23 120.0(4) . . ?
C19 C18 C26 123.2(4) . . ?
C23 C18 C26 116.8(4) . . ?
C18 C19 C20 121.2(4) . . ?
C21 C20 C19 119.5(4) . . ?
C20 C21 C22 120.0(4) . . ?
C20 C21 C25 119.5(4) . . ?
C22 C21 C25 120.5(3) . . ?
C21 C22 C14 121.3(3) . . ?
C21 C22 C23 119.8(4) . . ?
C14 C22 C23 118.9(4) . . ?
C18 C23 C22 119.4(4) . . ?
C18 C23 C17 121.8(4) . . ?
C22 C23 C17 118.8(4) . . ?
O3 C24 N4 120.3(3) . . ?
O3 C24 C14 122.8(4) . . ?
N4 C24 C14 116.8(3) . . ?
O4 C25 N4 120.3(3) . . ?
O4 C25 C21 123.5(4) . . ?
N4 C25 C21 116.1(3) . . ?
N1 C26 C13 127.5(4) . . ?
N1 C26 C18 117.7(4) . . ?
C13 C26 C18 114.8(3) . . ?
C28 C27 C32 121.8(3) . . ?
C28 C27 N3 119.0(3) . . ?
C32 C27 N3 119.1(3) . . ?
C27 C28 C29 118.3(3) . . ?
C27 C28 C33 122.6(3) . . ?
C29 C28 C33 119.0(3) . . ?
C30 C29 C28 121.8(4) . . ?
C29 C30 C31 118.3(4) . . ?
C29 C30 C34 120.8(4) . . ?
C31 C30 C34 121.0(3) . . ?
C30 C31 C32 121.8(3) . . ?
C27 C32 C31 118.0(3) . . ?
C27 C32 C35 120.9(4) . . ?
C31 C32 C35 121.1(3) . . ?
C41 C36 C37 121.8(3) . . ?
C41 C36 N4 120.0(3) . . ?
C37 C36 N4 118.1(3) . . ?
C38 C37 C36 117.8(3) . . ?
C38 C37 C42 119.8(3) . . ?
C36 C37 C42 122.4(3) . . ?
C39 C38 C37 121.8(3) . . ?
C40 C39 C38 118.6(3) . . ?
C40 C39 C43 120.7(3) . . ?
C38 C39 C43 120.7(4) . . ?
C39 C40 C41 121.7(3) . . ?
C40 C41 C36 118.2(3) . . ?
C40 C41 C44 120.4(3) . . ?
C36 C41 C44 121.3(4) . . ?
C46 C45 C50 120.0 . . ?
C46 C45 Cl1 121.5(2) . . ?
C50 C45 Cl1 118.5(2) . . ?
C45 C46 C47 120.0 . . ?
C45 C46 Cl2 121.1(2) . . ?
C47 C46 Cl2 118.9(2) . . ?
C46 C47 C48 120.0 . . ?
C47 C48 C49 120.0 . . ?
C50 C49 C48 120.0 . . ?
C49 C50 C45 120.0 . . ?
C26 N1 C4 117.7(4) . . ?
C13 N2 C17 117.5(4) . . ?
C11 N3 C12 124.4(3) . . ?
C11 N3 C27 118.4(3) . . ?
C12 N3 C27 117.1(3) . . ?
C24 N4 C25 124.9(3) . . ?
C24 N4 C36 118.3(3) . . ?
C25 N4 C36 116.6(3) . . ?
C54 C55 C51 120.0 . . ?
C55 C54 C52 120.0 . . ?
C56 C52 C54 120.0 . . ?
C52 C56 C53 120.0 . . ?
C52 C56 Cl4 121.5(12) . . ?
C53 C56 Cl4 118.5(12) . . ?
C56 C53 C51 120.0 . . ?
C56 C53 Cl3 122.6(13) . . ?
C51 C53 Cl3 117.4(13) . . ?
C53 C51 C55 120.0 . . ?
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 1.390(6) . ?
C1 C9 1.407(5) . ?
C1 C11 1.472(5) . ?
C2 C3 1.382(6) . ?
C3 C4 1.368(6) . ?
C4 N1 1.400(5) . ?
C4 C10 1.430(6) . ?
C5 C6 1.372(6) . ?
C5 C10 1.394(6) . ?
C5 C13 1.482(6) . ?
C6 C7 1.411(6) . ?
C7 C8 1.380(5) . ?
C8 C9 1.400(6) . ?
C8 C12 1.477(6) . ?
C9 C10 1.425(5) . ?
C11 O1 1.221(4) . ?
C11 N3 1.400(5) . ?
C12 O2 1.214(5) . ?
C12 N3 1.405(5) . ?
C13 N2 1.275(5) . ?
C13 C26 1.465(6) . ?
C14 C15 1.389(5) . ?
C14 C22 1.409(5) . ?
C14 C24 1.467(5) . ?
C15 C16 1.388(5) . ?
C16 C17 1.366(6) . ?
C17 N2 1.401(5) . ?
C17 C23 1.430(6) . ?
C18 C19 1.378(6) . ?
C18 C23 1.392(6) . ?
C18 C26 1.491(6) . ?
C19 C20 1.401(6) . ?
C20 C21 1.389(6) . ?
C21 C22 1.397(6) . ?
C21 C25 1.475(5) . ?
C22 C23 1.421(5) . ?
C24 O3 1.218(4) . ?
C24 N4 1.406(5) . ?
C25 O4 1.212(5) . ?
C25 N4 1.408(5) . ?
C26 N1 1.278(5) . ?
C27 C28 1.386(5) . ?
C27 C32 1.388(5) . ?
C27 N3 1.447(5) . ?
C28 C29 1.387(5) . ?
C28 C33 1.498(5) . ?
C29 C30 1.383(5) . ?
C30 C31 1.388(5) . ?
C30 C34 1.509(5) . ?
C31 C32 1.390(5) . ?
C32 C35 1.501(5) . ?
C36 C41 1.390(5) . ?
C36 C37 1.393(5) . ?
C36 N4 1.448(5) . ?
C37 C38 1.389(5) . ?
C37 C42 1.501(5) . ?
C38 C39 1.386(5) . ?
C39 C40 1.383(5) . ?
C39 C43 1.508(5) . ?
C40 C41 1.386(5) . ?
C41 C44 1.505(5) . ?
C45 C46 1.3900 . ?
C45 C50 1.3900 . ?
C45 Cl1 1.715(3) . ?
C46 C47 1.3900 . ?
C46 Cl2 1.721(3) . ?
C47 C48 1.3900 . ?
C48 C49 1.3900 . ?
C49 C50 1.3900 . ?
Cl3 C53 1.692(16) . ?
Cl4 C56 1.724(16) . ?
C55 C54 1.3900 . ?
C55 C51 1.3900 . ?
C54 C52 1.3900 . ?
C52 C56 1.3900 . ?
C56 C53 1.3900 . ?
C53 C51 1.3900 . ?
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
C9 C1 C2 C3 2.5(6) . . . . ?
C11 C1 C2 C3 -174.3(4) . . . . ?
C1 C2 C3 C4 1.8(6) . . . . ?
C2 C3 C4 N1 175.6(4) . . . . ?
C2 C3 C4 C10 -4.6(6) . . . . ?
C10 C5 C6 C7 1.8(6) . . . . ?
C13 C5 C6 C7 -176.7(3) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C6 C7 C8 C9 -2.8(6) . . . . ?
C6 C7 C8 C12 175.8(4) . . . . ?
C7 C8 C9 C1 -179.9(4) . . . . ?
C12 C8 C9 C1 1.4(5) . . . . ?
C7 C8 C9 C10 1.5(5) . . . . ?
C12 C8 C9 C10 -177.2(3) . . . . ?
C2 C1 C9 C8 177.5(4) . . . . ?
C11 C1 C9 C8 -5.6(5) . . . . ?
C2 C1 C9 C10 -3.9(5) . . . . ?
C11 C1 C9 C10 173.0(3) . . . . ?
C6 C5 C10 C9 -3.1(6) . . . . ?
C13 C5 C10 C9 175.4(3) . . . . ?
C6 C5 C10 C4 178.7(4) . . . . ?
C13 C5 C10 C4 -2.8(5) . . . . ?
C8 C9 C10 C5 1.5(5) . . . . ?
C1 C9 C10 C5 -177.1(3) . . . . ?
C8 C9 C10 C4 179.7(3) . . . . ?
C1 C9 C10 C4 1.1(5) . . . . ?
C3 C4 C10 C5 -178.6(4) . . . . ?
N1 C4 C10 C5 1.1(6) . . . . ?
C3 C4 C10 C9 3.1(5) . . . . ?
N1 C4 C10 C9 -177.1(3) . . . . ?
C2 C1 C11 O1 2.5(6) . . . . ?
C9 C1 C11 O1 -174.4(3) . . . . ?
C2 C1 C11 N3 -178.7(3) . . . . ?
C9 C1 C11 N3 4.4(5) . . . . ?
C7 C8 C12 O2 4.2(6) . . . . ?
C9 C8 C12 O2 -177.1(4) . . . . ?
C7 C8 C12 N3 -174.9(3) . . . . ?
C9 C8 C12 N3 3.8(5) . . . . ?
C6 C5 C13 N2 2.0(6) . . . . ?
C10 C5 C13 N2 -176.5(3) . . . . ?
C6 C5 C13 C26 -179.6(4) . . . . ?
C10 C5 C13 C26 1.9(5) . . . . ?
C22 C14 C15 C16 -1.4(6) . . . . ?
C24 C14 C15 C16 175.4(3) . . . . ?
C14 C15 C16 C17 -2.6(6) . . . . ?
C15 C16 C17 N2 -175.3(3) . . . . ?
C15 C16 C17 C23 4.7(6) . . . . ?
C23 C18 C19 C20 -2.2(6) . . . . ?
C26 C18 C19 C20 176.6(4) . . . . ?
C18 C19 C20 C21 -0.5(6) . . . . ?
C19 C20 C21 C22 1.8(6) . . . . ?
C19 C20 C21 C25 -177.7(4) . . . . ?
C20 C21 C22 C14 -179.2(4) . . . . ?
C25 C21 C22 C14 0.3(6) . . . . ?
C20 C21 C22 C23 -0.3(6) . . . . ?
C25 C21 C22 C23 179.2(3) . . . . ?
C15 C14 C22 C21 -177.8(3) . . . . ?
C24 C14 C22 C21 5.3(5) . . . . ?
C15 C14 C22 C23 3.2(5) . . . . ?
C24 C14 C22 C23 -173.6(3) . . . . ?
C19 C18 C23 C22 3.6(6) . . . . ?
C26 C18 C23 C22 -175.3(3) . . . . ?
C19 C18 C23 C17 -178.7(4) . . . . ?
C26 C18 C23 C17 2.5(5) . . . . ?
C21 C22 C23 C18 -2.3(5) . . . . ?
C14 C22 C23 C18 176.6(3) . . . . ?
C21 C22 C23 C17 179.8(3) . . . . ?
C14 C22 C23 C17 -1.2(5) . . . . ?
C16 C17 C23 C18 179.5(4) . . . . ?
N2 C17 C23 C18 -0.5(6) . . . . ?
C16 C17 C23 C22 -2.7(5) . . . . ?
N2 C17 C23 C22 177.3(3) . . . . ?
C15 C14 C24 O3 -3.2(5) . . . . ?
C22 C14 C24 O3 173.6(3) . . . . ?
C15 C14 C24 N4 177.5(3) . . . . ?
C22 C14 C24 N4 -5.7(5) . . . . ?
C20 C21 C25 O4 -4.9(6) . . . . ?
C22 C21 C25 O4 175.6(4) . . . . ?
C20 C21 C25 N4 174.3(3) . . . . ?
C22 C21 C25 N4 -5.2(5) . . . . ?
N2 C13 C26 N1 179.0(4) . . . . ?
C5 C13 C26 N1 0.8(6) . . . . ?
N2 C13 C26 C18 -2.5(6) . . . . ?
C5 C13 C26 C18 179.3(3) . . . . ?
C19 C18 C26 N1 -1.4(6) . . . . ?
C23 C18 C26 N1 177.4(3) . . . . ?
C19 C18 C26 C13 180.0(4) . . . . ?
C23 C18 C26 C13 -1.2(5) . . . . ?
C32 C27 C28 C29 0.2(5) . . . . ?
N3 C27 C28 C29 -177.6(3) . . . . ?
C32 C27 C28 C33 179.5(3) . . . . ?
N3 C27 C28 C33 1.6(5) . . . . ?
C27 C28 C29 C30 0.1(5) . . . . ?
C33 C28 C29 C30 -179.2(3) . . . . ?
C28 C29 C30 C31 -0.3(6) . . . . ?
C28 C29 C30 C34 179.4(3) . . . . ?
C29 C30 C31 C32 0.2(6) . . . . ?
C34 C30 C31 C32 -179.5(4) . . . . ?
C28 C27 C32 C31 -0.3(6) . . . . ?
N3 C27 C32 C31 177.5(3) . . . . ?
C28 C27 C32 C35 -179.5(4) . . . . ?
N3 C27 C32 C35 -1.6(6) . . . . ?
C30 C31 C32 C27 0.1(6) . . . . ?
C30 C31 C32 C35 179.3(4) . . . . ?
C41 C36 C37 C38 -2.2(5) . . . . ?
N4 C36 C37 C38 176.0(3) . . . . ?
C41 C36 C37 C42 178.1(3) . . . . ?
N4 C36 C37 C42 -3.7(5) . . . . ?
C36 C37 C38 C39 1.1(5) . . . . ?
C42 C37 C38 C39 -179.2(3) . . . . ?
C37 C38 C39 C40 1.0(6) . . . . ?
C37 C38 C39 C43 -178.5(3) . . . . ?
C38 C39 C40 C41 -2.1(6) . . . . ?
C43 C39 C40 C41 177.4(4) . . . . ?
C39 C40 C41 C36 1.1(6) . . . . ?
C39 C40 C41 C44 -179.5(4) . . . . ?
C37 C36 C41 C40 1.1(5) . . . . ?
N4 C36 C41 C40 -177.0(3) . . . . ?
C37 C36 C41 C44 -178.3(4) . . . . ?
N4 C36 C41 C44 3.5(5) . . . . ?
C50 C45 C46 C47 0.0 . . . . ?
Cl1 C45 C46 C47 -179.7(3) . . . . ?
C50 C45 C46 Cl2 -179.9(3) . . . . ?
Cl1 C45 C46 Cl2 0.4(2) . . . . ?
C45 C46 C47 C48 0.0 . . . . ?
Cl2 C46 C47 C48 179.9(3) . . . . ?
C46 C47 C48 C49 0.0 . . . . ?
C47 C48 C49 C50 0.0 . . . . ?
C48 C49 C50 C45 0.0 . . . . ?
C46 C45 C50 C49 0.0 . . . . ?
Cl1 C45 C50 C49 179.7(3) . . . . ?
C13 C26 N1 C4 -2.5(6) . . . . ?
C18 C26 N1 C4 179.0(3) . . . . ?
C3 C4 N1 C26 -178.7(4) . . . . ?
C10 C4 N1 C26 1.6(5) . . . . ?
C26 C13 N2 C17 4.5(6) . . . . ?
C5 C13 N2 C17 -177.3(3) . . . . ?
C16 C17 N2 C13 177.0(3) . . . . ?
C23 C17 N2 C13 -2.9(5) . . . . ?
O1 C11 N3 C12 179.9(3) . . . . ?
C1 C11 N3 C12 1.0(5) . . . . ?
O1 C11 N3 C27 -0.8(5) . . . . ?
C1 C11 N3 C27 -179.6(3) . . . . ?
O2 C12 N3 C11 175.9(4) . . . . ?
C8 C12 N3 C11 -5.1(5) . . . . ?
O2 C12 N3 C27 -3.5(5) . . . . ?
C8 C12 N3 C27 175.6(3) . . . . ?
C28 C27 N3 C11 -101.9(4) . . . . ?
C32 C27 N3 C11 80.2(4) . . . . ?
C28 C27 N3 C12 77.5(4) . . . . ?
C32 C27 N3 C12 -100.5(4) . . . . ?
O3 C24 N4 C25 -178.9(3) . . . . ?
C14 C24 N4 C25 0.4(5) . . . . ?
O3 C24 N4 C36 5.1(5) . . . . ?
C14 C24 N4 C36 -175.6(3) . . . . ?
O4 C25 N4 C24 -175.9(3) . . . . ?
C21 C25 N4 C24 4.9(5) . . . . ?
O4 C25 N4 C36 0.2(5) . . . . ?
C21 C25 N4 C36 -179.0(3) . . . . ?
C41 C36 N4 C24 -78.0(4) . . . . ?
C37 C36 N4 C24 103.8(4) . . . . ?
C41 C36 N4 C25 105.7(4) . . . . ?
C37 C36 N4 C25 -72.6(4) . . . . ?
C51 C55 C54 C52 0.0 . . . . ?
C55 C54 C52 C56 0.0 . . . . ?
C54 C52 C56 C53 0.0 . . . . ?
C54 C52 C56 Cl4 -178.4(16) . . . . ?
C52 C56 C53 C51 0.0 . . . . ?
Cl4 C56 C53 C51 178.5(15) . . . . ?
C52 C56 C53 Cl3 -179.9(17) . . . . ?
Cl4 C56 C53 Cl3 -1.4(14) . . . . ?
C56 C53 C51 C55 0.0 . . . . ?
Cl3 C53 C51 C55 179.9(16) . . . . ?
C54 C55 C51 C53 0.0 . . . . ?
