#------------------------------------------------------------------------------
#$Date: 2023-04-05 18:35:32 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282415 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/20/2312045.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312045
loop_
_publ_author_name
'Parkin, Sean'
'Glidewell, Christopher'
'Horton, Peter N.'
_publ_section_title
;
 (E,E)-1,1'-[1,2-Bis(4-chlorophenyl)ethane-1,2-diyl]bis(phenyldiazene)
 revisited: threefold configurational disorder of (S,S), (R,R) and (S,R)
 isomers, a detailed critique.
;
_journal_coeditor_code           FA3399
_journal_issue                   'Pt 3'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              77
_journal_page_last               82
_journal_paper_doi               10.1107/S2053229623001262
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C26 H20 Cl2 N4'
_chemical_formula_moiety         'C26 H20 Cl2 N4'
_chemical_formula_sum            'C26 H20 Cl2 N4'
_chemical_formula_weight         459.36
_chemical_name_systematic
;
1,1'-[1,2-Bis(4-chlorophenyl)ethane-1,2-diyl]bis(phenyldiazene)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/2
_cell_angle_alpha                90
_cell_angle_beta                 99.967(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.657(10)
_cell_length_b                   5.4399(18)
_cell_length_c                   19.086(6)
_cell_measurement_reflns_used    3065
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.289
_cell_measurement_theta_min      2.167
_cell_volume                     2316.9(15)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_molecular_graphics
;
ShelXle (Hübschle et al.,  2011)
;
_computing_publication_material
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'Rigaku AFC12'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8691
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.289
_diffrn_reflns_theta_min         2.581
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrystalClear-SM Expert; Rigaku, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     861
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0546P)²+0.7288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                2189
_reflns_number_total             3064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fa3399sup1.cif
_cod_data_source_block           IId
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2312045
_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   0.864
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1A 0.2560(2) 0.8602(10) 0.4658(3) 0.0335(6) Uani d 0.3872(15) A -1
H H1A 0.266805 1.021496 0.489719 0.040 Uiso calc 0.3872(15) A -1
N N1A 0.1905(3) 0.8497(18) 0.4411(5) 0.0316(14) Uani d 0.3872(15) A -1
N N2A 0.1627(3) 1.029(2) 0.4592(7) 0.0387(19) Uani d 0.3872(15) A -1
C C2A 0.0987(2) 1.0154(13) 0.4364(4) 0.0373(15) Uani d 0.3872(15) A -1
C C3A 0.0661(3) 1.2216(12) 0.4495(4) 0.0458(18) Uani d 0.3872(15) A -1
H H3A 0.085878 1.357083 0.474880 0.055 Uiso calc 0.3872(15) A -1
C C4A 0.0046(3) 1.2298(11) 0.4256(5) 0.0505(16) Uani d 0.3872(15) A -1
H H4A -0.017655 1.370765 0.434551 0.061 Uiso calc 0.3872(15) A -1
C C5A -0.0243(2) 1.0316(13) 0.3884(4) 0.078(3) Uani d 0.3872(15) A -1
H H5A -0.066312 1.037165 0.372072 0.093 Uiso calc 0.3872(15) A -1
C C6A 0.0083(3) 0.8253(12) 0.3753(4) 0.0561(18) Uani d 0.3872(15) A -1
H H6A -0.011436 0.689881 0.349922 0.067 Uiso calc 0.3872(15) A -1
C C7A 0.0698(3) 0.8172(11) 0.3992(4) 0.053(3) Uani d 0.3872(15) A -1
H H7A 0.092097 0.676195 0.390251 0.064 Uiso calc 0.3872(15) A -1
C C8A 0.2844(3) 0.8418(13) 0.4001(3) 0.0319(16) Uani d 0.3872(15) A -1
C C9A 0.2717(4) 0.6441(12) 0.3539(3) 0.0317(13) Uani d 0.3872(15) A -1
H H9A 0.244095 0.521363 0.362868 0.038 Uiso calc 0.3872(15) A -1
C C10A 0.2992(4) 0.6259(13) 0.2944(3) 0.0306(19) Uani d 0.3872(15) A -1
H H10A 0.290483 0.490800 0.262791 0.037 Uiso calc 0.3872(15) A -1
C C11A 0.3396(3) 0.8055(15) 0.2812(3) 0.0361(13) Uani d 0.3872(15) A -1
C C12A 0.3523(3) 1.0032(14) 0.3275(4) 0.036(2) Uani d 0.3872(15) A -1
H H12A 0.379898 1.125937 0.318505 0.044 Uiso calc 0.3872(15) A -1
C C13A 0.3248(3) 1.0214(13) 0.3870(4) 0.0315(12) Uani d 0.3872(15) A -1
H H13A 0.333510 1.156503 0.418582 0.038 Uiso calc 0.3872(15) A -1
Cl Cl1A 0.3769(3) 0.7838(15) 0.2129(3) 0.0646(13) Uani d 0.3872(15) A -1
C C1B 0.2723(2) 0.6498(10) 0.5200(3) 0.0335(6) Uani d 0.3872(15) A -1
H H1B 0.252509 0.495925 0.499115 0.040 Uiso calc 0.3872(15) A -1
N N1B 0.24731(18) 0.7122(8) 0.5845(2) 0.0341(9) Uani d 0.3872(15) A -1
N N2B 0.2068(2) 0.5765(10) 0.5955(3) 0.0328(11) Uani d 0.3872(15) A -1
C C2B 0.18189(14) 0.6356(6) 0.65794(14) 0.0354(9) Uani d 0.3872(15) A -1
C C3B 0.14065(15) 0.4667(5) 0.67521(17) 0.0431(19) Uani d 0.3872(15) A -1
H H3B 0.130853 0.324851 0.646533 0.052 Uiso calc 0.3872(15) A -1
C C4B 0.11375(17) 0.5055(6) 0.7344(2) 0.0563(13) Uani d 0.3872(15) A -1
H H4B 0.085565 0.390077 0.746232 0.068 Uiso calc 0.3872(15) A -1
C C5B 0.12809(18) 0.7131(7) 0.77638(17) 0.051(3) Uani d 0.3872(15) A -1
H H5B 0.109703 0.739569 0.816860 0.061 Uiso calc 0.3872(15) A -1
C C6B 0.16933(16) 0.8819(6) 0.75911(16) 0.0433(10) Uani d 0.3872(15) A -1
H H6B 0.179128 1.023837 0.787789 0.052 Uiso calc 0.3872(15) A -1
C C7B 0.19623(13) 0.8432(6) 0.69989(17) 0.039(2) Uani d 0.3872(15) A -1
H H7B 0.224417 0.958615 0.688089 0.046 Uiso calc 0.3872(15) A -1
C C8B 0.33890(10) 0.5998(6) 0.54131(18) 0.0321(13) Uani d 0.3872(15) A -1
C C9B 0.37486(12) 0.7636(5) 0.58553(18) 0.0387(9) Uani d 0.3872(15) A -1
H H9B 0.358182 0.910966 0.600339 0.046 Uiso calc 0.3872(15) A -1
C C10B 0.43524(12) 0.7118(5) 0.60807(17) 0.039(2) Uani d 0.3872(15) A -1
H H10B 0.459820 0.823703 0.638290 0.046 Uiso calc 0.3872(15) A -1
C C11B 0.45965(10) 0.4961(6) 0.58640(18) 0.0412(9) Uani d 0.3872(15) A -1
C C12B 0.42368(14) 0.3323(5) 0.54218(19) 0.0407(15) Uani d 0.3872(15) A -1
H H12B 0.440366 0.184964 0.527366 0.049 Uiso calc 0.3872(15) A -1
C C13B 0.36331(13) 0.3842(6) 0.51963(18) 0.0361(10) Uani d 0.3872(15) A -1
H H13B 0.338728 0.272223 0.489414 0.043 Uiso calc 0.3872(15) A -1
Cl Cl1B 0.53413(7) 0.4299(4) 0.61552(9) 0.0560(6) Uani d 0.3872(15) A -1
C C1C 0.2425(3) 0.8584(15) 0.4751(5) 0.0335(6) Uani d 0.226(3) A 2
H H1C 0.253229 1.018067 0.499987 0.040 Uiso calc 0.226(3) A 2
N N1C 0.1773(5) 0.839(3) 0.4496(9) 0.032(3) Uani d 0.226(3) A 2
N N2C 0.1497(5) 1.028(3) 0.4619(11) 0.030(2) Uani d 0.226(3) A 2
C C2C 0.0872(4) 1.019(2) 0.4313(7) 0.037(3) Uani d 0.226(3) A 2
C C3C 0.0506(5) 1.190(2) 0.4570(7) 0.041(3) Uani d 0.226(3) A 2
H H3C 0.067208 1.300989 0.493527 0.050 Uiso calc 0.226(3) A 2
C C4C -0.0102(4) 1.198(2) 0.4291(8) 0.045(2) Uani d 0.226(3) A 2
H H4C -0.035240 1.315177 0.446638 0.054 Uiso calc 0.226(3) A 2
C C5C -0.0345(4) 1.036(2) 0.3756(8) 0.078(3) Uani d 0.226(3) A 2
H H5C -0.076091 1.041555 0.356587 0.093 Uiso calc 0.226(3) A 2
C C6C 0.0021(6) 0.865(2) 0.3500(5) 0.059(3) Uani d 0.226(3) A 2
H H6C -0.014496 0.753742 0.313425 0.071 Uiso calc 0.226(3) A 2
C C7C 0.0629(5) 0.856(2) 0.3778(6) 0.042(3) Uani d 0.226(3) A 2
H H7C 0.087952 0.739549 0.360314 0.050 Uiso calc 0.226(3) A 2
C C8C 0.2744(6) 0.826(3) 0.4121(6) 0.034(3) Uani d 0.226(3) A 2
C C9C 0.2663(7) 0.619(2) 0.3687(6) 0.042(3) Uani d 0.226(3) A 2
H H9C 0.240773 0.490356 0.378766 0.050 Uiso calc 0.226(3) A 2
C C10C 0.2956(8) 0.601(2) 0.3107(6) 0.041(3) Uani d 0.226(3) A 2
H H10C 0.290082 0.459898 0.281044 0.049 Uiso calc 0.226(3) A 2
C C11C 0.3329(7) 0.790(3) 0.2960(6) 0.042(2) Uani d 0.226(3) A 2
C C12C 0.3410(6) 0.997(2) 0.3393(7) 0.037(2) Uani d 0.226(3) A 2
H H12C 0.366535 1.126037 0.329250 0.044 Uiso calc 0.226(3) A 2
C C13C 0.3117(6) 1.015(2) 0.3973(7) 0.039(3) Uani d 0.226(3) A 2
H H13C 0.317226 1.156500 0.426972 0.046 Uiso calc 0.226(3) A 2
Cl Cl1C 0.3681(5) 0.756(3) 0.2176(5) 0.065(2) Uani d 0.226(3) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1A C1A C8A . . 106.4(5) ?
N1A C1A C1B . . 107.2(5) ?
C8A C1A C1B . . 114.9(5) ?
N1A C1A H1A . . 109.4 ?
C8A C1A H1A . . 109.4 ?
C1B C1A H1A . . 109.4 ?
N2A N1A C1A . . 114.2(7) ?
N1A N2A C2A . . 114.0(7) ?
C3A C2A C7A . . 120.0 ?
C3A C2A N2A . . 116.2(5) ?
C7A C2A N2A . . 123.7(5) ?
C2A C3A C4A . . 120.0 ?
C2A C3A H3A . . 120.0 ?
C4A C3A H3A . . 120.0 ?
C3A C4A C5A . . 120.0 ?
C3A C4A H4A . . 120.0 ?
C5A C4A H4A . . 120.0 ?
C6A C5A C4A . . 120.0 ?
C6A C5A H5A . . 120.0 ?
C4A C5A H5A . . 120.0 ?
C5A C6A C7A . . 120.0 ?
C5A C6A H6A . . 120.0 ?
C7A C6A H6A . . 120.0 ?
C6A C7A C2A . . 120.0 ?
C6A C7A H7A . . 120.0 ?
C2A C7A H7A . . 120.0 ?
C9A C8A C13A . . 120.0 ?
C9A C8A C1A . . 120.5(4) ?
C13A C8A C1A . . 119.5(4) ?
C8A C9A C10A . . 120.0 ?
C8A C9A H9A . . 120.0 ?
C10A C9A H9A . . 120.0 ?
C11A C10A C9A . . 120.0 ?
C11A C10A H10A . . 120.0 ?
C9A C10A H10A . . 120.0 ?
C10A C11A C12A . . 120.0 ?
C10A C11A Cl1A . . 121.8(4) ?
C12A C11A Cl1A . . 118.1(4) ?
C13A C12A C11A . . 120.0 ?
C13A C12A H12A . . 120.0 ?
C11A C12A H12A . . 120.0 ?
C12A C13A C8A . . 120.0 ?
C12A C13A H13A . . 120.0 ?
C8A C13A H13A . . 120.0 ?
N1B C1B C8B . . 108.9(4) ?
N1B C1B C1A . . 107.8(4) ?
C8B C1B C1A . . 115.1(4) ?
N1B C1B H1B . . 108.3 ?
C8B C1B H1B . . 108.3 ?
C1A C1B H1B . . 108.3 ?
N2B N1B C1B . . 114.3(4) ?
N1B N2B C2B . . 114.8(4) ?
C3B C2B C7B . . 120.0 ?
C3B C2B N2B . . 115.1(3) ?
C7B C2B N2B . . 124.9(3) ?
C2B C3B C4B . . 120.0 ?
C2B C3B H3B . . 120.0 ?
C4B C3B H3B . . 120.0 ?
C3B C4B C5B . . 120.0 ?
C3B C4B H4B . . 120.0 ?
C5B C4B H4B . . 120.0 ?
C6B C5B C4B . . 120.0 ?
C6B C5B H5B . . 120.0 ?
C4B C5B H5B . . 120.0 ?
C5B C6B C7B . . 120.0 ?
C5B C6B H6B . . 120.0 ?
C7B C6B H6B . . 120.0 ?
C6B C7B C2B . . 120.0 ?
C6B C7B H7B . . 120.0 ?
C2B C7B H7B . . 120.0 ?
C9B C8B C13B . . 120.0 ?
C9B C8B C1B . . 119.9(3) ?
C13B C8B C1B . . 120.0(3) ?
C10B C9B C8B . . 120.0 ?
C10B C9B H9B . . 120.0 ?
C8B C9B H9B . . 120.0 ?
C11B C10B C9B . . 120.0 ?
C11B C10B H10B . . 120.0 ?
C9B C10B H10B . . 120.0 ?
C10B C11B C12B . . 120.0 ?
C10B C11B Cl1B . . 119.93(19) ?
C12B C11B Cl1B . . 120.06(19) ?
C13B C12B C11B . . 120.0 ?
C13B C12B H12B . . 120.0 ?
C11B C12B H12B . . 120.0 ?
C12B C13B C8B . . 120.0 ?
C12B C13B H13B . . 120.0 ?
C8B C13B H13B . . 120.0 ?
N1C C1C C8C . . 108.5(9) ?
N1C C1C C1C . 7_566 104.7(10) ?
C8C C1C C1C . 7_566 108.7(9) ?
N1C C1C H1C . . 111.5 ?
C8C C1C H1C . . 111.5 ?
C1C C1C H1C 7_566 . 111.5 ?
N2C N1C C1C . . 112.7(11) ?
N1C N2C C2C . . 112.9(11) ?
C3C C2C C7C . . 120.0 ?
C3C C2C N2C . . 116.2(8) ?
C7C C2C N2C . . 123.8(8) ?
C2C C3C C4C . . 120.0 ?
C2C C3C H3C . . 120.0 ?
C4C C3C H3C . . 120.0 ?
C3C C4C C5C . . 120.0 ?
C3C C4C H4C . . 120.0 ?
C5C C4C H4C . . 120.0 ?
C6C C5C C4C . . 120.0 ?
C6C C5C H5C . . 120.0 ?
C4C C5C H5C . . 120.0 ?
C5C C6C C7C . . 120.0 ?
C5C C6C H6C . . 120.0 ?
C7C C6C H6C . . 120.0 ?
C6C C7C C2C . . 120.0 ?
C6C C7C H7C . . 120.0 ?
C2C C7C H7C . . 120.0 ?
C9C C8C C13C . . 120.0 ?
C9C C8C C1C . . 122.2(7) ?
C13C C8C C1C . . 117.7(7) ?
C10C C9C C8C . . 120.0 ?
C10C C9C H9C . . 120.0 ?
C8C C9C H9C . . 120.0 ?
C9C C10C C11C . . 120.0 ?
C9C C10C H10C . . 120.0 ?
C11C C10C H10C . . 120.0 ?
C10C C11C C12C . . 120.0 ?
C10C C11C Cl1C . . 117.3(7) ?
C12C C11C Cl1C . . 122.7(7) ?
C13C C12C C11C . . 120.0 ?
C13C C12C H12C . . 120.0 ?
C11C C12C H12C . . 120.0 ?
C12C C13C C8C . . 120.0 ?
C12C C13C H13C . . 120.0 ?
C8C C13C H13C . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1A N1A . 1.479(6) ?
C1A C8A . 1.508(5) ?
C1A C1B . 1.545(6) ?
C1A H1A . 1.0000 ?
N1A N2A . 1.242(7) ?
N2A C2A . 1.442(6) ?
C2A C3A . 1.3900 ?
C2A C7A . 1.3900 ?
C3A C4A . 1.3900 ?
C3A H3A . 0.9500 ?
C4A C5A . 1.3900 ?
C4A H4A . 0.9500 ?
C5A C6A . 1.3900 ?
C5A H5A . 0.9500 ?
C6A C7A . 1.3900 ?
C6A H6A . 0.9500 ?
C7A H7A . 0.9500 ?
C8A C9A . 1.3900 ?
C8A C13A . 1.3900 ?
C9A C10A . 1.3900 ?
C9A H9A . 0.9500 ?
C10A C11A . 1.3900 ?
C10A H10A . 0.9500 ?
C11A C12A . 1.3900 ?
C11A Cl1A . 1.678(7) ?
C12A C13A . 1.3900 ?
C12A H12A . 0.9500 ?
C13A H13A . 0.9500 ?
C1B N1B . 1.480(6) ?
C1B C8B . 1.517(5) ?
C1B H1B . 1.0000 ?
N1B N2B . 1.224(5) ?
N2B C2B . 1.441(5) ?
C2B C3B . 1.3900 ?
C2B C7B . 1.3900 ?
C3B C4B . 1.3900 ?
C3B H3B . 0.9500 ?
C4B C5B . 1.3900 ?
C4B H4B . 0.9500 ?
C5B C6B . 1.3900 ?
C5B H5B . 0.9500 ?
C6B C7B . 1.3900 ?
C6B H6B . 0.9500 ?
C7B H7B . 0.9500 ?
C8B C9B . 1.3900 ?
C8B C13B . 1.3900 ?
C9B C10B . 1.3900 ?
C9B H9B . 0.9500 ?
C10B C11B . 1.3900 ?
C10B H10B . 0.9500 ?
C11B C12B . 1.3900 ?
C11B Cl1B . 1.721(3) ?
C12B C13B . 1.3900 ?
C12B H12B . 0.9500 ?
C13B H13B . 0.9500 ?
C1C N1C . 1.475(11) ?
C1C C8C . 1.517(8) ?
C1C C1C 7_566 1.517(13) ?
C1C H1C . 1.0000 ?
N1C N2C . 1.245(12) ?
N2C C2C . 1.436(10) ?
C2C C3C . 1.3900 ?
C2C C7C . 1.3900 ?
C3C C4C . 1.3900 ?
C3C H3C . 0.9500 ?
C4C C5C . 1.3900 ?
C4C H4C . 0.9500 ?
C5C C6C . 1.3900 ?
C5C H5C . 0.9500 ?
C6C C7C . 1.3900 ?
C6C H6C . 0.9500 ?
C7C H7C . 0.9500 ?
C8C C9C . 1.3900 ?
C8C C13C . 1.3900 ?
C9C C10C . 1.3900 ?
C9C H9C . 0.9500 ?
C10C C11C . 1.3900 ?
C10C H10C . 0.9500 ?
C11C C12C . 1.3900 ?
C11C Cl1C . 1.822(12) ?
C12C C13C . 1.3900 ?
C12C H12C . 0.9500 ?
C13C H13C . 0.9500 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A C1A N1A N2A . . . . -123.0(10) ?
C1B C1A N1A N2A . . . . 113.6(10) ?
C1A N1A N2A C2A . . . . -178.7(8) ?
N1A N2A C2A C3A . . . . -174.3(9) ?
N1A N2A C2A C7A . . . . 1.8(14) ?
C7A C2A C3A C4A . . . . 0.0 ?
N2A C2A C3A C4A . . . . 176.2(8) ?
C2A C3A C4A C5A . . . . 0.0 ?
C3A C4A C5A C6A . . . . 0.0 ?
C4A C5A C6A C7A . . . . 0.0 ?
C5A C6A C7A C2A . . . . 0.0 ?
C3A C2A C7A C6A . . . . 0.0 ?
N2A C2A C7A C6A . . . . -175.9(9) ?
N1A C1A C8A C9A . . . . -56.0(7) ?
C1B C1A C8A C9A . . . . 62.5(6) ?
N1A C1A C8A C13A . . . . 125.6(6) ?
C1B C1A C8A C13A . . . . -116.0(5) ?
C13A C8A C9A C10A . . . . 0.0 ?
C1A C8A C9A C10A . . . . -178.5(6) ?
C8A C9A C10A C11A . . . . 0.0 ?
C9A C10A C11A C12A . . . . 0.0 ?
C9A C10A C11A Cl1A . . . . 176.5(7) ?
C10A C11A C12A C13A . . . . 0.0 ?
Cl1A C11A C12A C13A . . . . -176.6(6) ?
C11A C12A C13A C8A . . . . 0.0 ?
C9A C8A C13A C12A . . . . 0.0 ?
C1A C8A C13A C12A . . . . 178.5(6) ?
N1A C1A C1B N1B . . . . -69.1(6) ?
C8A C1A C1B N1B . . . . 172.9(4) ?
N1A C1A C1B C8B . . . . 169.1(5) ?
C8A C1A C1B C8B . . . . 51.1(6) ?
C8B C1B N1B N2B . . . . -121.7(5) ?
C1A C1B N1B N2B . . . . 112.8(6) ?
C1B N1B N2B C2B . . . . -179.8(4) ?
N1B N2B C2B C3B . . . . -173.1(4) ?
N1B N2B C2B C7B . . . . 7.0(7) ?
C7B C2B C3B C4B . . . . 0.0 ?
N2B C2B C3B C4B . . . . -179.9(4) ?
C2B C3B C4B C5B . . . . 0.0 ?
C3B C4B C5B C6B . . . . 0.0 ?
C4B C5B C6B C7B . . . . 0.0 ?
C5B C6B C7B C2B . . . . 0.0 ?
C3B C2B C7B C6B . . . . 0.0 ?
N2B C2B C7B C6B . . . . 179.9(4) ?
N1B C1B C8B C9B . . . . -48.4(4) ?
C1A C1B C8B C9B . . . . 72.8(5) ?
N1B C1B C8B C13B . . . . 128.3(3) ?
C1A C1B C8B C13B . . . . -110.5(4) ?
C13B C8B C9B C10B . . . . 0.0 ?
C1B C8B C9B C10B . . . . 176.7(3) ?
C8B C9B C10B C11B . . . . 0.0 ?
C9B C10B C11B C12B . . . . 0.0 ?
C9B C10B C11B Cl1B . . . . -179.0(3) ?
C10B C11B C12B C13B . . . . 0.0 ?
Cl1B C11B C12B C13B . . . . 178.9(3) ?
C11B C12B C13B C8B . . . . 0.0 ?
C9B C8B C13B C12B . . . . 0.0 ?
C1B C8B C13B C12B . . . . -176.7(3) ?
C8C C1C N1C N2C . . . . -120.6(16) ?
C1C C1C N1C N2C 7_566 . . . 123.4(17) ?
C1C N1C N2C C2C . . . . 174.4(13) ?
N1C N2C C2C C3C . . . . 164.3(14) ?
N1C N2C C2C C7C . . . . -17(2) ?
C7C C2C C3C C4C . . . . 0.0 ?
N2C C2C C3C C4C . . . . 178.5(13) ?
C2C C3C C4C C5C . . . . 0.0 ?
C3C C4C C5C C6C . . . . 0.0 ?
C4C C5C C6C C7C . . . . 0.0 ?
C5C C6C C7C C2C . . . . 0.0 ?
C3C C2C C7C C6C . . . . 0.0 ?
N2C C2C C7C C6C . . . . -178.3(14) ?
N1C C1C C8C C9C . . . . -56.3(13) ?
C1C C1C C8C C9C 7_566 . . . 57.1(13) ?
N1C C1C C8C C13C . . . . 122.3(11) ?
C1C C1C C8C C13C 7_566 . . . -124.3(10) ?
C13C C8C C9C C10C . . . . 0.0 ?
C1C C8C C9C C10C . . . . 178.6(12) ?
C8C C9C C10C C11C . . . . 0.0 ?
C9C C10C C11C C12C . . . . 0.0 ?
C9C C10C C11C Cl1C . . . . -178.4(11) ?
C10C C11C C12C C13C . . . . 0.0 ?
Cl1C C11C C12C C13C . . . . 178.3(12) ?
C11C C12C C13C C8C . . . . 0.0 ?
C9C C8C C13C C12C . . . . 0.0 ?
C1C C8C C13C C12C . . . . -178.6(11) ?

_cod_database_fobs_code 2312045
