#------------------------------------------------------------------------------
#$Date: 2020-03-26 01:37:56 +0200 (Thu, 26 Mar 2020) $
#$Revision: 249708 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/45/4134540.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_4134540
loop_
_publ_author_name
'Konrad, David B.'
'Savasci, Gökcen'
'Allmendinger, Lars'
'Trauner, Dirk'
'Ochsenfeld, Christian'
'Ali, Ahmed M.'
_publ_section_title
;
 Computational Design and Synthesis of a Deeply Red-Shifted and Bistable
 Azobenzene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b10430
_journal_year                    2020
_chemical_formula_moiety         'C12 H6 Cl4 N2'
_chemical_formula_sum            'C12 H6 Cl4 N2'
_chemical_formula_weight         319.99
_chemical_name_common            621
_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_block_code                C12H6Cl4N2_uv093_trauner
_audit_creation_date
;
'Tue Aug 30 07:57:05 2016'
;
_audit_creation_method           SHELXL-2014
_audit_update_record             30-Aug-16
_cell_angle_alpha                94.3451(16)
_cell_angle_beta                 92.6148(17)
_cell_angle_gamma                118.514(2)
_cell_formula_units_Z            6
_cell_length_a                   8.14609(18)
_cell_length_b                   8.27819(16)
_cell_length_c                   32.9320(6)
_cell_measurement_reflns_used    4524
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.1880
_cell_measurement_theta_min      4.4190
_cell_volume                     1937.28(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
Acta Cryst. A64, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -64.00   52.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.9988   77.0000 -150.0000 232

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00   53.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.9988   77.0000   90.0000 234

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00  104.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       26.0925   77.0000  -30.0000 234

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0245825000
_diffrn_orient_matrix_UB_12      0.0730674000
_diffrn_orient_matrix_UB_13      0.0157753000
_diffrn_orient_matrix_UB_21      0.0227401000
_diffrn_orient_matrix_UB_22      0.0635746000
_diffrn_orient_matrix_UB_23      -0.0148067000
_diffrn_orient_matrix_UB_31      -0.0937240000
_diffrn_orient_matrix_UB_32      -0.0157066000
_diffrn_orient_matrix_UB_33      -0.0016054000
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            10570
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         4.363
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.161
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0318
_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)+(0.0299P)²+0.7877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6902
_reflns_number_total             7833
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b10430_si_003.cif
_cod_data_source_block           uo093
_cod_database_code               4134540
_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.
;
_shelxl_version_number           2014-3
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 0.1902(2) 0.9262(2) 0.02615(5) 0.0239(4) Uani 1 1 d . . . . .
C2 C 0.0464(3) 0.8027(2) -0.00305(6) 0.0262(4) Uani 1 1 d . . . . .
C3 C 0.0469(3) 0.8333(3) -0.04365(6) 0.0322(4) Uani 1 1 d . . . . .
H3 H -0.0521 0.7475 -0.0631 0.039 Uiso 1 1 calc R U . . .
C4 C 0.1929(3) 0.9903(3) -0.05568(6) 0.0361(5) Uani 1 1 d . . . . .
H4 H 0.1947 1.0114 -0.0836 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3362(3) 1.1168(3) -0.02758(6) 0.0342(4) Uani 1 1 d . . . . .
H5 H 0.4359 1.2247 -0.0361 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3335(3) 1.0849(3) 0.01311(6) 0.0280(4) Uani 1 1 d . . . . .
C7 C 0.2974(2) 0.8790(2) 0.12869(6) 0.0267(4) Uani 1 1 d . . . . .
C8 C 0.3179(3) 0.7331(3) 0.14182(6) 0.0280(4) Uani 1 1 d . . . . .
C9 C 0.2986(3) 0.6930(3) 0.18180(6) 0.0333(4) Uani 1 1 d . . . . .
H9 H 0.3071 0.5894 0.1899 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2667(3) 0.8049(3) 0.20973(6) 0.0369(5) Uani 1 1 d . . . . .
H10 H 0.2524 0.7774 0.2373 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2552(3) 0.9571(3) 0.19823(6) 0.0352(4) Uani 1 1 d . . . . .
H11 H 0.2384 1.0367 0.2179 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2685(3) 0.9918(3) 0.15776(6) 0.0303(4) Uani 1 1 d . . . . .
C13 C 0.7594(2) 0.5074(2) 0.19803(5) 0.0230(4) Uani 1 1 d . . . . .
C14 C 0.7907(2) 0.6311(2) 0.16923(6) 0.0257(4) Uani 1 1 d . . . . .
C15 C 0.8311(3) 0.5991(3) 0.13007(6) 0.0306(4) Uani 1 1 d . . . . .
H15 H 0.8474 0.6831 0.1105 0.037 Uiso 1 1 calc R U . . .
C16 C 0.8472(3) 0.4424(3) 0.11995(6) 0.0340(4) Uani 1 1 d . . . . .
H16 H 0.8761 0.4193 0.0932 0.041 Uiso 1 1 calc R U . . .
C17 C 0.8220(3) 0.3195(3) 0.14805(6) 0.0338(4) Uani 1 1 d . . . . .
H17 H 0.8353 0.2134 0.1408 0.041 Uiso 1 1 calc R U . . .
C18 C 0.7773(2) 0.3505(2) 0.18687(6) 0.0272(4) Uani 1 1 d . . . . .
C19 C 0.5783(2) 0.4817(2) 0.29450(5) 0.0254(4) Uani 1 1 d . . . . .
C20 C 0.4079(3) 0.4686(3) 0.30398(6) 0.0278(4) Uani 1 1 d . . . . .
C21 C 0.3786(3) 0.5124(3) 0.34318(6) 0.0374(5) Uani 1 1 d . . . . .
H21 H 0.2626 0.5065 0.3488 0.045 Uiso 1 1 calc R U . . .
C22 C 0.5200(3) 0.5651(3) 0.37409(6) 0.0462(6) Uani 1 1 d . . . . .
H22 H 0.5012 0.5962 0.4012 0.055 Uiso 1 1 calc R U . . .
C23 C 0.6887(3) 0.5731(3) 0.36616(6) 0.0421(5) Uani 1 1 d . . . . .
H23 H 0.7839 0.6059 0.3878 0.050 Uiso 1 1 calc R U . . .
C24 C 0.7177(3) 0.5330(3) 0.32652(6) 0.0316(4) Uani 1 1 d . . . . .
C25 C 0.7494(3) 0.0918(3) 0.36773(6) 0.0340(4) Uani 1 1 d . . . . .
C26 C 0.6489(3) 0.0072(3) 0.32986(6) 0.0382(5) Uani 1 1 d . . . . .
C27 C 0.7270(4) -0.0497(3) 0.29936(7) 0.0441(5) Uani 1 1 d . . . . .
H27 H 0.6568 -0.1079 0.2737 0.053 Uiso 1 1 calc R U . . .
C28 C 0.9064(4) -0.0217(3) 0.30632(8) 0.0506(6) Uani 1 1 d . . . . .
H28 H 0.9601 -0.0611 0.2854 0.061 Uiso 1 1 calc R U . . .
C29 C 1.0103(3) 0.0632(3) 0.34351(8) 0.0465(6) Uani 1 1 d . . . . .
H29 H 1.1344 0.0819 0.3482 0.056 Uiso 1 1 calc R U . . .
C30 C 0.9308(3) 0.1205(3) 0.37377(6) 0.0375(5) Uani 1 1 d . . . . .
C31 C 0.4753(3) 0.0930(3) 0.44839(5) 0.0275(4) Uani 1 1 d . . . . .
C32 C 0.5578(3) 0.2574(3) 0.47506(6) 0.0287(4) Uani 1 1 d . . . . .
C33 C 0.4669(3) 0.2794(3) 0.50775(6) 0.0329(4) Uani 1 1 d . . . . .
H33 H 0.5245 0.3914 0.5256 0.039 Uiso 1 1 calc R U . . .
C34 C 0.2928(3) 0.1393(3) 0.51449(6) 0.0358(5) Uani 1 1 d . . . . .
H34 H 0.2313 0.1551 0.5371 0.043 Uiso 1 1 calc R U . . .
C35 C 0.2076(3) -0.0236(3) 0.48867(6) 0.0345(4) Uani 1 1 d . . . . .
H35 H 0.0875 -0.1200 0.4932 0.041 Uiso 1 1 calc R U . . .
C36 C 0.2987(3) -0.0448(3) 0.45624(6) 0.0307(4) Uani 1 1 d . . . . .
N1 N 0.1712(2) 0.8908(2) 0.06819(5) 0.0262(3) Uani 1 1 d . . . . .
N2 N 0.3176(2) 0.9090(2) 0.08628(5) 0.0292(3) Uani 1 1 d . . . . .
N3 N 0.7309(2) 0.5576(2) 0.23864(4) 0.0250(3) Uani 1 1 d . . . . .
N4 N 0.5954(2) 0.4309(2) 0.25293(5) 0.0265(3) Uani 1 1 d . . . . .
N5 N 0.6710(3) 0.1598(3) 0.39877(6) 0.0496(5) Uani 1 1 d . . . . .
N6 N 0.5626(3) 0.0415(2) 0.41672(5) 0.0403(4) Uani 1 1 d . . . . .
Cl1 Cl -0.13740(7) 0.60501(6) 0.01200(2) 0.03447(11) Uani 1 1 d . . . . .
Cl2 Cl 0.50428(7) 1.25698(7) 0.04803(2) 0.04678(14) Uani 1 1 d . . . . .
Cl3 Cl 0.35958(8) 0.59379(7) 0.10640(2) 0.03811(12) Uani 1 1 d . . . . .
Cl4 Cl 0.25477(8) 1.18361(7) 0.14396(2) 0.04457(14) Uani 1 1 d . . . . .
Cl5 Cl 0.77710(7) 0.83043(6) 0.18281(2) 0.03410(11) Uani 1 1 d . . . . .
Cl6 Cl 0.76016(8) 0.19962(7) 0.22219(2) 0.03932(12) Uani 1 1 d . . . . .
Cl7 Cl 0.22952(7) 0.40074(8) 0.26505(2) 0.03805(12) Uani 1 1 d . . . . .
Cl8 Cl 0.92948(7) 0.54144(9) 0.31747(2) 0.04669(14) Uani 1 1 d . . . . .
Cl9 Cl 0.42300(9) -0.02780(11) 0.32056(2) 0.06163(18) Uani 1 1 d . . . . .
Cl10 Cl 1.06118(8) 0.22892(9) 0.42054(2) 0.05366(16) Uani 1 1 d . . . . .
Cl11 Cl 0.78055(7) 0.43516(7) 0.47023(2) 0.04069(13) Uani 1 1 d . . . . .
Cl12 Cl 0.18886(7) -0.25037(8) 0.42395(2) 0.04816(15) 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.66(16) . . ?
C6 C1 N1 124.17(16) . . ?
C2 C1 N1 117.86(15) . . ?
C3 C2 C1 121.62(17) . . ?
C3 C2 Cl1 119.13(15) . . ?
C1 C2 Cl1 119.25(14) . . ?
C2 C3 C4 119.21(18) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.80(18) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.39(18) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 121.29(18) . . ?
C5 C6 Cl2 117.80(15) . . ?
C1 C6 Cl2 120.73(14) . . ?
C8 C7 C12 117.96(17) . . ?
C8 C7 N2 117.65(17) . . ?
C12 C7 N2 124.30(17) . . ?
C9 C8 C7 121.53(18) . . ?
C9 C8 Cl3 119.57(15) . . ?
C7 C8 Cl3 118.85(14) . . ?
C10 C9 C8 119.16(19) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.89(18) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.22(19) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C7 121.09(18) . . ?
C11 C12 Cl4 118.58(16) . . ?
C7 C12 Cl4 120.31(15) . . ?
C14 C13 C18 117.95(16) . . ?
C14 C13 N3 118.12(15) . . ?
C18 C13 N3 123.57(16) . . ?
C15 C14 C13 121.99(17) . . ?
C15 C14 Cl5 119.11(15) . . ?
C13 C14 Cl5 118.90(13) . . ?
C14 C15 C16 118.61(18) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 120.90(18) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.04(18) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.47(18) . . ?
C17 C18 Cl6 118.48(14) . . ?
C13 C18 Cl6 120.91(14) . . ?
C20 C19 C24 117.74(17) . . ?
C20 C19 N4 118.00(16) . . ?
C24 C19 N4 124.14(16) . . ?
C21 C20 C19 121.85(18) . . ?
C21 C20 Cl7 119.08(15) . . ?
C19 C20 Cl7 119.05(14) . . ?
C20 C21 C22 118.99(19) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C23 120.9(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 119.45(19) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C19 121.04(18) . . ?
C23 C24 Cl8 118.54(16) . . ?
C19 C24 Cl8 120.39(15) . . ?
C30 C25 C26 118.28(18) . . ?
C30 C25 N5 120.80(19) . . ?
C26 C25 N5 120.77(19) . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 Cl9 119.08(18) . . ?
C25 C26 Cl9 119.96(16) . . ?
C28 C27 C26 119.6(2) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.8(2) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C30 C29 C28 119.1(2) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C25 C30 C29 121.3(2) . . ?
C25 C30 Cl10 119.32(15) . . ?
C29 C30 Cl10 119.40(18) . . ?
C36 C31 C32 117.12(17) . . ?
C36 C31 N6 115.73(16) . . ?
C32 C31 N6 126.67(17) . . ?
C33 C32 C31 120.77(18) . . ?
C33 C32 Cl11 117.25(15) . . ?
C31 C32 Cl11 121.90(14) . . ?
C34 C33 C32 120.18(18) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C35 C34 C33 120.41(18) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 119.14(19) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C35 C36 C31 122.38(18) . . ?
C35 C36 Cl12 118.51(15) . . ?
C31 C36 Cl12 119.11(14) . . ?
N2 N1 C1 113.03(15) . . ?
N1 N2 C7 112.13(15) . . ?
N4 N3 C13 113.60(14) . . ?
N3 N4 C19 112.13(15) . . ?
N6 N5 C25 112.91(18) . . ?
N5 N6 C31 117.86(18) . . ?
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 C6 1.393(2) . ?
C1 C2 1.396(3) . ?
C1 N1 1.437(2) . ?
C2 C3 1.380(3) . ?
C2 Cl1 1.7369(18) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 Cl2 1.7325(19) . ?
C7 C8 1.392(3) . ?
C7 C12 1.392(3) . ?
C7 N2 1.440(2) . ?
C8 C9 1.380(3) . ?
C8 Cl3 1.7358(19) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 Cl4 1.7359(19) . ?
C13 C14 1.390(2) . ?
C13 C18 1.398(2) . ?
C13 N3 1.432(2) . ?
C14 C15 1.382(3) . ?
C14 Cl5 1.7332(18) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 Cl6 1.7327(19) . ?
C19 C20 1.391(2) . ?
C19 C24 1.394(3) . ?
C19 N4 1.434(2) . ?
C20 C21 1.377(3) . ?
C20 Cl7 1.7358(19) . ?
C21 C22 1.378(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 Cl8 1.7338(19) . ?
C25 C30 1.382(3) . ?
C25 C26 1.394(3) . ?
C25 N5 1.444(3) . ?
C26 C27 1.382(3) . ?
C26 Cl9 1.729(2) . ?
C27 C28 1.372(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9500 . ?
C30 Cl10 1.743(2) . ?
C31 C36 1.397(3) . ?
C31 C32 1.402(3) . ?
C31 N6 1.437(2) . ?
C32 C33 1.383(3) . ?
C32 Cl11 1.7307(19) . ?
C33 C34 1.379(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.375(3) . ?
C35 H35 0.9500 . ?
C36 Cl12 1.736(2) . ?
N1 N2 1.245(2) . ?
N3 N4 1.248(2) . ?
N5 N6 1.182(2) . ?
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 1.4(3) . . . . ?
N1 C1 C2 C3 175.27(16) . . . . ?
C6 C1 C2 Cl1 -178.83(13) . . . . ?
N1 C1 C2 Cl1 -5.0(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
Cl1 C2 C3 C4 -179.95(14) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 Cl2 -174.23(15) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
N1 C1 C6 C5 -175.24(17) . . . . ?
C2 C1 C6 Cl2 173.27(13) . . . . ?
N1 C1 C6 Cl2 -0.2(2) . . . . ?
C12 C7 C8 C9 4.1(3) . . . . ?
N2 C7 C8 C9 -179.19(17) . . . . ?
C12 C7 C8 Cl3 -178.51(14) . . . . ?
N2 C7 C8 Cl3 -1.8(2) . . . . ?
C7 C8 C9 C10 -3.0(3) . . . . ?
Cl3 C8 C9 C10 179.61(15) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 2.6(3) . . . . ?
C10 C11 C12 C7 -1.5(3) . . . . ?
C10 C11 C12 Cl4 -179.74(15) . . . . ?
C8 C7 C12 C11 -1.8(3) . . . . ?
N2 C7 C12 C11 -178.30(17) . . . . ?
C8 C7 C12 Cl4 176.43(14) . . . . ?
N2 C7 C12 Cl4 -0.1(3) . . . . ?
C18 C13 C14 C15 2.6(3) . . . . ?
N3 C13 C14 C15 175.90(16) . . . . ?
C18 C13 C14 Cl5 -177.89(13) . . . . ?
N3 C13 C14 Cl5 -4.5(2) . . . . ?
C13 C14 C15 C16 -2.4(3) . . . . ?
Cl5 C14 C15 C16 178.06(14) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C13 -0.7(3) . . . . ?
C16 C17 C18 Cl6 -176.32(15) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
N3 C13 C18 C17 -173.93(16) . . . . ?
C14 C13 C18 Cl6 174.54(13) . . . . ?
N3 C13 C18 Cl6 1.6(2) . . . . ?
C24 C19 C20 C21 2.9(3) . . . . ?
N4 C19 C20 C21 179.21(17) . . . . ?
C24 C19 C20 Cl7 -178.77(14) . . . . ?
N4 C19 C20 Cl7 -2.5(2) . . . . ?
C19 C20 C21 C22 -2.1(3) . . . . ?
Cl7 C20 C21 C22 179.57(17) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C24 1.9(4) . . . . ?
C22 C23 C24 C19 -1.0(3) . . . . ?
C22 C23 C24 Cl8 -179.24(18) . . . . ?
C20 C19 C24 C23 -1.3(3) . . . . ?
N4 C19 C24 C23 -177.34(18) . . . . ?
C20 C19 C24 Cl8 176.86(14) . . . . ?
N4 C19 C24 Cl8 0.8(3) . . . . ?
C30 C25 C26 C27 1.2(3) . . . . ?
N5 C25 C26 C27 176.74(19) . . . . ?
C30 C25 C26 Cl9 -178.84(15) . . . . ?
N5 C25 C26 Cl9 -3.3(3) . . . . ?
C25 C26 C27 C28 -0.4(3) . . . . ?
Cl9 C26 C27 C28 179.64(17) . . . . ?
C26 C27 C28 C29 -0.1(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C26 C25 C30 C29 -1.5(3) . . . . ?
N5 C25 C30 C29 -177.07(19) . . . . ?
C26 C25 C30 Cl10 179.09(15) . . . . ?
N5 C25 C30 Cl10 3.5(3) . . . . ?
C28 C29 C30 C25 1.0(3) . . . . ?
C28 C29 C30 Cl10 -179.56(17) . . . . ?
C36 C31 C32 C33 0.4(3) . . . . ?
N6 C31 C32 C33 -171.28(18) . . . . ?
C36 C31 C32 Cl11 177.06(14) . . . . ?
N6 C31 C32 Cl11 5.4(3) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
Cl11 C32 C33 C34 -176.90(15) . . . . ?
C32 C33 C34 C35 -0.3(3) . . . . ?
C33 C34 C35 C36 0.3(3) . . . . ?
C34 C35 C36 C31 0.1(3) . . . . ?
C34 C35 C36 Cl12 -179.75(15) . . . . ?
C32 C31 C36 C35 -0.4(3) . . . . ?
N6 C31 C36 C35 172.21(18) . . . . ?
C32 C31 C36 Cl12 179.41(14) . . . . ?
N6 C31 C36 Cl12 -8.0(2) . . . . ?
C6 C1 N1 N2 -51.6(2) . . . . ?
C2 C1 N1 N2 134.97(17) . . . . ?
C1 N1 N2 C7 178.09(14) . . . . ?
C8 C7 N2 N1 118.06(18) . . . . ?
C12 C7 N2 N1 -65.4(2) . . . . ?
C14 C13 N3 N4 133.92(17) . . . . ?
C18 C13 N3 N4 -53.1(2) . . . . ?
C13 N3 N4 C19 176.25(14) . . . . ?
C20 C19 N4 N3 124.66(17) . . . . ?
C24 C19 N4 N3 -59.3(2) . . . . ?
C30 C25 N5 N6 -104.8(2) . . . . ?
C26 C25 N5 N6 79.7(3) . . . . ?
C25 N5 N6 C31 -179.97(17) . . . . ?
C36 C31 N6 N5 153.0(2) . . . . ?
C32 C31 N6 N5 -35.2(3) . . . . ?
