#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:34:49 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/49/4134964.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_4134964
loop_
_publ_author_name
'Nakamura, Kimihiro'
'Li, Qiang-Qiang'
'Krejčí, Ondřej'
'Foster, Adam S.'
'Sun, Kewei'
'Kawai, Shigeki'
'Ito, Shingo'
_publ_section_title
;
 On-Surface Synthesis of a π-Extended Diaza[8]circulene.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02534
_journal_year                    2020
_chemical_formula_sum            'C65 H52 Cl2 N2'
_chemical_formula_weight         931.98
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.7281(8)
_cell_length_b                   15.4483(9)
_cell_length_c                   30.7824(13)
_cell_measurement_reflns_used    3839
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      24.9628
_cell_measurement_theta_min      2.4498
_cell_volume                     9381.4(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1888
_diffrn_reflns_av_unetI/netI     0.1029
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            62905
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.45
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3920
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.799
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         8896
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0669
_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)+(0.0693P)²+9.9876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1903
_reflns_number_gt                5487
_reflns_number_total             8896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c02534_si_004.cif
_cod_data_source_block           9b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4134964
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.61662(17) 0.6855(3) 0.61936(11) 0.0248(8) Uani d . . . 1.0 . .
C C2 0.66356(18) 0.6177(3) 0.59914(12) 0.0308(9) Uani d . . . 1.0 . .
H H2A 0.668235 0.56856 0.61902 0.046 Uiso calc U . R 1.0 . .
H H2B 0.708209 0.643502 0.593881 0.046 Uiso calc U . R 1.0 . .
H H2C 0.644301 0.597764 0.571557 0.046 Uiso calc U . R 1.0 . .
C C3 0.60512(19) 0.7592(3) 0.58653(12) 0.0301(9) Uani d . . . 1.0 . .
H H3A 0.584209 0.735819 0.56015 0.045 Uiso calc U . R 1.0 . .
H H3B 0.648701 0.785908 0.579191 0.045 Uiso calc U . R 1.0 . .
H H3C 0.57512 0.802844 0.59936 0.045 Uiso calc U . R 1.0 . .
C C4 0.65188(19) 0.7238(3) 0.65940(12) 0.0346(10) Uani d . . . 1.0 . .
H H4A 0.6237 0.77003 0.671659 0.052 Uiso calc U . R 1.0 . .
H H4B 0.695987 0.747628 0.650918 0.052 Uiso calc U . R 1.0 . .
H H4C 0.658459 0.678377 0.681192 0.052 Uiso calc U . R 1.0 . .
C C5 0.54727(16) 0.6465(2) 0.63047(10) 0.0206(8) Uani d . . . 1.0 . .
C C6 0.51071(16) 0.6733(2) 0.66647(11) 0.0214(8) Uani d . . . 1.0 . .
H H6 0.530301 0.714802 0.685495 0.026 Uiso calc U . R 1.0 . .
C C7 0.44588(16) 0.6414(2) 0.67577(10) 0.0192(7) Uani d . . . 1.0 . .
C C8 0.41761(16) 0.5819(2) 0.64672(10) 0.0180(7) Uani d . . . 1.0 . .
C C9 0.45316(16) 0.5518(2) 0.60982(10) 0.0184(7) Uani d . . . 1.0 . .
C C10 0.51759(17) 0.5861(2) 0.60278(11) 0.0212(8) Uani d . . . 1.0 . .
H H10 0.542347 0.567418 0.578026 0.025 Uiso calc U . R 1.0 . .
C C11 0.42099(17) 0.4879(2) 0.58123(10) 0.0200(7) Uani d . . . 1.0 . .
C C12 0.45589(17) 0.4525(2) 0.54589(10) 0.0211(8) Uani d . . . 1.0 . .
H H12 0.501125 0.470458 0.540319 0.025 Uiso calc U . R 1.0 . .
C C13 0.42638(18) 0.3928(2) 0.51923(11) 0.0231(8) Uani d . . . 1.0 . .
H H13 0.45145 0.368975 0.49574 0.028 Uiso calc U . R 1.0 . .
C C14 0.35981(18) 0.3665(2) 0.52627(11) 0.0241(8) Uani d . . . 1.0 . .
H H14 0.339197 0.325564 0.507404 0.029 Uiso calc U . R 1.0 . .
C C15 0.32395(18) 0.4002(2) 0.56076(10) 0.0220(8) Uani d . . . 1.0 . .
H H15 0.278146 0.383333 0.565081 0.026 Uiso calc U . R 1.0 . .
C C16 0.35400(17) 0.4591(2) 0.58955(10) 0.0186(7) Uani d . . . 1.0 . .
C C17 0.31917(16) 0.4915(2) 0.62762(10) 0.0184(7) Uani d . . . 1.0 . .
C C18 0.25586(17) 0.4775(2) 0.64690(10) 0.0192(7) Uani d . . . 1.0 . .
C C19 0.20281(17) 0.4148(2) 0.63357(10) 0.0182(7) Uani d . . . 1.0 . .
C C20 0.22034(17) 0.3270(2) 0.63109(11) 0.0218(8) Uani d . . . 1.0 . .
H H20 0.264646 0.309584 0.63944 0.026 Uiso calc U . R 1.0 . .
C C21 0.17496(18) 0.2652(2) 0.61685(11) 0.0256(8) Uani d . . . 1.0 . .
H H21 0.188469 0.206413 0.614413 0.031 Uiso calc U . R 1.0 . .
C C22 0.10961(18) 0.2897(2) 0.60616(11) 0.0239(8) Uani d . . . 1.0 . .
H H22 0.077886 0.24789 0.596273 0.029 Uiso calc U . R 1.0 . .
C C23 0.09090(17) 0.3753(2) 0.60995(10) 0.0202(8) Uani d . . . 1.0 . .
H H23 0.045632 0.391134 0.603076 0.024 Uiso calc U . R 1.0 . .
C C24 0.13613(17) 0.4400(2) 0.62360(10) 0.0186(7) Uani d . . . 1.0 . .
C C25 0.11072(17) 0.5320(2) 0.62312(10) 0.0188(7) Uani d . . . 1.0 . .
H H25 0.063131 0.528274 0.612086 0.023 Uiso calc U . R 1.0 . .
C C26 0.14827(18) 0.5943(2) 0.59072(10) 0.0206(8) Uani d . . . 1.0 . .
H H26 0.19831 0.587724 0.59473 0.025 Uiso calc U . R 1.0 . .
C C27 0.13101(18) 0.5778(2) 0.54389(11) 0.0239(8) Uani d . . . 1.0 . .
C C28 0.1725(2) 0.5256(3) 0.51836(11) 0.0304(9) Uani d . . . 1.0 . .
H H28 0.213679 0.503446 0.529928 0.036 Uiso calc U . R 1.0 . .
C C29 0.1538(2) 0.5059(3) 0.47591(12) 0.0365(10) Uani d . . . 1.0 . .
H H29 0.1823 0.471174 0.458133 0.044 Uiso calc U . R 1.0 . .
C C30 0.0930(2) 0.5376(3) 0.45998(12) 0.0383(11) Uani d . . . 1.0 . .
H H30 0.079041 0.522235 0.431468 0.046 Uiso calc U . R 1.0 . .
C C31 0.0528(2) 0.5905(3) 0.48442(11) 0.0306(9) Uani d . . . 1.0 . .
H H31 0.011727 0.612036 0.472485 0.037 Uiso calc U . R 1.0 . .
C C32 0.07127(19) 0.6135(2) 0.52711(11) 0.0244(8) Uani d . . . 1.0 . .
C C33 0.03226(18) 0.6739(2) 0.55406(11) 0.0225(8) Uani d . . . 1.0 . .
C C34 0.06180(17) 0.7060(2) 0.59289(10) 0.0187(7) Uani d . . . 1.0 . .
C C35 0.02627(17) 0.7667(2) 0.61785(10) 0.0197(7) Uani d . . . 1.0 . .
C C36 -0.03733(17) 0.7955(2) 0.60412(11) 0.0220(8) Uani d . . . 1.0 . .
H H36 -0.060812 0.836776 0.621339 0.026 Uiso calc U . R 1.0 . .
C C37 -0.06752(17) 0.7657(2) 0.56604(11) 0.0221(8) Uani d . . . 1.0 . .
C C38 -0.03094(18) 0.7043(2) 0.54200(11) 0.0249(8) Uani d . . . 1.0 . .
H H38 -0.050627 0.682386 0.516062 0.03 Uiso calc U . R 1.0 . .
C C39 -0.13622(18) 0.8001(2) 0.54981(12) 0.0294(9) Uani d U . D 1.0 . .
C C40 -0.1829(3) 0.7253(4) 0.5364(2) 0.0426(16) Uani d U P D 0.816(10) A 1
H H40A -0.185091 0.682719 0.559951 0.064 Uiso calc U P R 0.816(10) A 1
H H40B -0.16502 0.697721 0.510145 0.064 Uiso calc U P R 0.816(10) A 1
H H40C -0.228478 0.747793 0.530573 0.064 Uiso calc U P R 0.816(10) A 1
C C41 -0.1721(3) 0.8564(5) 0.5832(2) 0.0543(19) Uani d U P D 0.816(10) A 1
H H41A -0.181385 0.822198 0.609362 0.081 Uiso calc U P R 0.816(10) A 1
H H41B -0.214936 0.877583 0.57105 0.081 Uiso calc U P R 0.816(10) A 1
H H41C -0.143194 0.905748 0.590773 0.081 Uiso calc U P R 0.816(10) A 1
C C42 -0.1243(3) 0.8551(4) 0.5079(2) 0.0447(18) Uani d U P D 0.816(10) A 1
H H42A -0.1681 0.870794 0.495138 0.067 Uiso calc U P R 0.816(10) A 1
H H42B -0.098095 0.821088 0.486914 0.067 Uiso calc U P R 0.816(10) A 1
H H42C -0.099218 0.907752 0.515386 0.067 Uiso calc U P R 0.816(10) A 1
C C40A -0.1738(14) 0.7448(15) 0.5162(8) 0.049(5) Uani d U P D 0.184(10) A 2
H H40D -0.150478 0.748474 0.488184 0.074 Uiso calc U P R 0.184(10) A 2
H H40E -0.220381 0.76604 0.513044 0.074 Uiso calc U P R 0.184(10) A 2
H H40F -0.174723 0.684369 0.525951 0.074 Uiso calc U P R 0.184(10) A 2
C C41A -0.1830(12) 0.805(2) 0.5911(6) 0.047(5) Uani d U P D 0.184(10) A 2
H H41D -0.194041 0.745726 0.600658 0.071 Uiso calc U P R 0.184(10) A 2
H H41E -0.224861 0.83554 0.583893 0.071 Uiso calc U P R 0.184(10) A 2
H H41F -0.159232 0.835171 0.614449 0.071 Uiso calc U P R 0.184(10) A 2
C C42A -0.1299(10) 0.8930(10) 0.5330(9) 0.037(4) Uani d U P D 0.184(10) A 2
H H42D -0.117133 0.931382 0.557002 0.055 Uiso calc U P R 0.184(10) A 2
H H42E -0.173463 0.911703 0.52092 0.055 Uiso calc U P R 0.184(10) A 2
H H42F -0.095071 0.895409 0.510344 0.055 Uiso calc U P R 0.184(10) A 2
C C43 0.05801(16) 0.7993(2) 0.65827(10) 0.0190(7) Uani d . . . 1.0 . .
C C44 0.03639(17) 0.8743(2) 0.67927(10) 0.0216(8) Uani d . . . 1.0 . .
H H44 0.00062 0.907381 0.666985 0.026 Uiso calc U . R 1.0 . .
C C45 0.06590(17) 0.9014(2) 0.71753(11) 0.0222(8) Uani d . . . 1.0 . .
H H45 0.049539 0.951864 0.731759 0.027 Uiso calc U . R 1.0 . .
C C46 0.11915(18) 0.8555(2) 0.73517(11) 0.0247(8) Uani d . . . 1.0 . .
H H46 0.139345 0.873745 0.76164 0.03 Uiso calc U . R 1.0 . .
C C47 0.14292(17) 0.7825(2) 0.71398(11) 0.0223(8) Uani d . . . 1.0 . .
H H47 0.180282 0.751548 0.725719 0.027 Uiso calc U . R 1.0 . .
C C48 0.11284(16) 0.7539(2) 0.67577(10) 0.0188(7) Uani d . . . 1.0 . .
C C49 0.13922(17) 0.6751(2) 0.65257(10) 0.0196(8) Uani d . . . 1.0 . .
H H49 0.189117 0.671033 0.657917 0.024 Uiso calc U . R 1.0 . .
C C50 0.10617(16) 0.5874(2) 0.66588(10) 0.0179(7) Uani d . . . 1.0 . .
H H50 0.056885 0.600194 0.669893 0.022 Uiso calc U . R 1.0 . .
C C51 0.12972(17) 0.5499(2) 0.70869(10) 0.0190(7) Uani d . . . 1.0 . .
C C52 0.08307(17) 0.5449(2) 0.74285(11) 0.0211(8) Uani d . . . 1.0 . .
H H52 0.037972 0.564302 0.738093 0.025 Uiso calc U . R 1.0 . .
C C53 0.10028(18) 0.5130(2) 0.78307(11) 0.0233(8) Uani d . . . 1.0 . .
H H53 0.067487 0.51167 0.805656 0.028 Uiso calc U . R 1.0 . .
C C54 0.16508(18) 0.4828(2) 0.79071(11) 0.0249(8) Uani d . . . 1.0 . .
H H54 0.176615 0.4585 0.818074 0.03 Uiso calc U . R 1.0 . .
C C55 0.21283(17) 0.4884(2) 0.75811(11) 0.0228(8) Uani d . . . 1.0 . .
H H55 0.257648 0.468506 0.763389 0.027 Uiso calc U . R 1.0 . .
C C56 0.19638(17) 0.5230(2) 0.71726(10) 0.0186(7) Uani d . . . 1.0 . .
C C57 0.25241(16) 0.5290(2) 0.68490(10) 0.0185(7) Uani d . . . 1.0 . .
C C58 0.31271(16) 0.5743(2) 0.68910(10) 0.0187(7) Uani d . . . 1.0 . .
C C59 0.33903(16) 0.6382(2) 0.71901(10) 0.0185(7) Uani d . . . 1.0 . .
C C60 0.29948(17) 0.6714(2) 0.75344(11) 0.0228(8) Uani d . . . 1.0 . .
H H60 0.255162 0.649344 0.758253 0.027 Uiso calc U . R 1.0 . .
C C61 0.32451(18) 0.7353(3) 0.78007(11) 0.0273(9) Uani d . . . 1.0 . .
H H61 0.296694 0.758185 0.8025 0.033 Uiso calc U . R 1.0 . .
C C62 0.38978(18) 0.7669(3) 0.77465(12) 0.0290(9) Uani d . . . 1.0 . .
H H62 0.406854 0.8105 0.793457 0.035 Uiso calc U . R 1.0 . .
C C63 0.42963(18) 0.7343(3) 0.74166(11) 0.0264(8) Uani d . . . 1.0 . .
H H63 0.474743 0.754913 0.738524 0.032 Uiso calc U . R 1.0 . .
C C64 0.40542(16) 0.6718(2) 0.71272(10) 0.0203(8) Uani d . . . 1.0 . .
C C65 0.9054(2) 0.5749(3) 0.65637(17) 0.0567(14) Uani d . . . 1.0 . .
H H65A 0.907851 0.611851 0.682584 0.068 Uiso calc U . R 1.0 . .
H H65B 0.930837 0.6041 0.632828 0.068 Uiso calc U . R 1.0 . .
Cl Cl1 0.94369(5) 0.47300(8) 0.66762(3) 0.0402(3) Uani d . . . 1.0 . .
Cl Cl2 0.82072(6) 0.56268(12) 0.64077(4) 0.0682(5) Uani d . . . 1.0 . .
N N1 0.35260(13) 0.55035(18) 0.65399(8) 0.0171(6) Uani d . . . 1.0 . .
N N2 0.12805(14) 0.68047(19) 0.60538(8) 0.0188(6) Uani d . . . 1.0 . .
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
C2 C1 C4 . . 108.5(3) ?
C2 C1 C5 . . 111.2(3) ?
C4 C1 C5 . . 112.1(3) ?
C2 C1 C3 . . 109.2(3) ?
C4 C1 C3 . . 108.0(3) ?
C5 C1 C3 . . 107.8(3) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1 C3 H3A . . 109.5 ?
C1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C1 C4 H4A . . 109.5 ?
C1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C6 C5 C10 . . 118.1(3) ?
C6 C5 C1 . . 121.7(3) ?
C10 C5 C1 . . 120.1(3) ?
C5 C6 C7 . . 122.3(3) ?
C5 C6 H6 . . 118.9 ?
C7 C6 H6 . . 118.9 ?
C8 C7 C6 . . 117.7(3) ?
C8 C7 C64 . . 119.3(3) ?
C6 C7 C64 . . 122.9(3) ?
N1 C8 C7 . . 119.7(3) ?
N1 C8 C9 . . 118.1(3) ?
C7 C8 C9 . . 122.2(3) ?
C10 C9 C8 . . 116.9(3) ?
C10 C9 C11 . . 123.8(3) ?
C8 C9 C11 . . 119.3(3) ?
C9 C10 C5 . . 122.9(3) ?
C9 C10 H10 . . 118.6 ?
C5 C10 H10 . . 118.6 ?
C12 C11 C16 . . 118.5(3) ?
C12 C11 C9 . . 121.1(3) ?
C16 C11 C9 . . 120.4(3) ?
C13 C12 C11 . . 121.5(3) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C12 C13 C14 . . 120.4(3) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 C13 . . 119.6(3) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C14 C15 C16 . . 121.0(3) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C15 C16 C11 . . 118.9(3) ?
C15 C16 C17 . . 122.4(3) ?
C11 C16 C17 . . 118.7(3) ?
N1 C17 C18 . . 106.1(3) ?
N1 C17 C16 . . 118.4(3) ?
C18 C17 C16 . . 135.5(3) ?
C17 C18 C57 . . 107.8(3) ?
C17 C18 C19 . . 127.8(3) ?
C57 C18 C19 . . 124.1(3) ?
C20 C19 C24 . . 119.1(3) ?
C20 C19 C18 . . 118.2(3) ?
C24 C19 C18 . . 122.6(3) ?
C21 C20 C19 . . 121.8(3) ?
C21 C20 H20 . . 119.1 ?
C19 C20 H20 . . 119.1 ?
C20 C21 C22 . . 119.4(3) ?
C20 C21 H21 . . 120.3 ?
C22 C21 H21 . . 120.3 ?
C23 C22 C21 . . 119.5(3) ?
C23 C22 H22 . . 120.3 ?
C21 C22 H22 . . 120.3 ?
C22 C23 C24 . . 122.6(3) ?
C22 C23 H23 . . 118.7 ?
C24 C23 H23 . . 118.7 ?
C23 C24 C19 . . 117.6(3) ?
C23 C24 C25 . . 117.2(3) ?
C19 C24 C25 . . 125.1(3) ?
C24 C25 C50 . . 121.6(3) ?
C24 C25 C26 . . 115.3(3) ?
C50 C25 C26 . . 103.0(3) ?
C24 C25 H25 . . 105.2 ?
C50 C25 H25 . . 105.2 ?
C26 C25 H25 . . 105.2 ?
N2 C26 C27 . . 112.9(3) ?
N2 C26 C25 . . 103.5(3) ?
C27 C26 C25 . . 113.4(3) ?
N2 C26 H26 . . 108.9 ?
C27 C26 H26 . . 108.9 ?
C25 C26 H26 . . 108.9 ?
C28 C27 C32 . . 121.0(3) ?
C28 C27 C26 . . 120.4(3) ?
C32 C27 C26 . . 118.5(3) ?
C29 C28 C27 . . 120.0(4) ?
C29 C28 H28 . . 120.0 ?
C27 C28 H28 . . 120.0 ?
C30 C29 C28 . . 119.0(4) ?
C30 C29 H29 . . 120.5 ?
C28 C29 H29 . . 120.5 ?
C31 C30 C29 . . 121.3(4) ?
C31 C30 H30 . . 119.3 ?
C29 C30 H30 . . 119.3 ?
C30 C31 C32 . . 121.0(4) ?
C30 C31 H31 . . 119.5 ?
C32 C31 H31 . . 119.5 ?
C27 C32 C31 . . 117.5(3) ?
C27 C32 C33 . . 118.9(3) ?
C31 C32 C33 . . 123.5(3) ?
C38 C33 C34 . . 118.6(3) ?
C38 C33 C32 . . 122.5(3) ?
C34 C33 C32 . . 118.9(3) ?
C35 C34 N2 . . 119.9(3) ?
C35 C34 C33 . . 119.4(3) ?
N2 C34 C33 . . 120.7(3) ?
C36 C35 C34 . . 119.8(3) ?
C36 C35 C43 . . 121.8(3) ?
C34 C35 C43 . . 118.5(3) ?
C37 C36 C35 . . 122.2(3) ?
C37 C36 H36 . . 118.9 ?
C35 C36 H36 . . 118.9 ?
C36 C37 C38 . . 116.6(3) ?
C36 C37 C39 . . 122.3(3) ?
C38 C37 C39 . . 121.0(3) ?
C33 C38 C37 . . 123.5(3) ?
C33 C38 H38 . . 118.3 ?
C37 C38 H38 . . 118.3 ?
C41 C39 C40 . . 109.4(4) ?
C42A C39 C40A . . 109.5(9) ?
C41 C39 C37 . . 112.9(4) ?
C42A C39 C37 . . 111.3(8) ?
C40 C39 C37 . . 110.8(4) ?
C40A C39 C37 . . 116.8(11) ?
C41 C39 C42 . . 108.5(4) ?
C40 C39 C42 . . 106.1(4) ?
C37 C39 C42 . . 108.9(3) ?
C42A C39 C41A . . 106.3(9) ?
C40A C39 C41A . . 106.6(10) ?
C37 C39 C41A . . 105.6(10) ?
C39 C40 H40A . . 109.5 ?
C39 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
C39 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 109.5 ?
C39 C41 H41A . . 109.5 ?
C39 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C39 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C39 C42 H42A . . 109.5 ?
C39 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C39 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C39 C40A H40D . . 109.5 ?
C39 C40A H40E . . 109.5 ?
H40D C40A H40E . . 109.5 ?
C39 C40A H40F . . 109.5 ?
H40D C40A H40F . . 109.5 ?
H40E C40A H40F . . 109.5 ?
C39 C41A H41D . . 109.5 ?
C39 C41A H41E . . 109.5 ?
H41D C41A H41E . . 109.5 ?
C39 C41A H41F . . 109.5 ?
H41D C41A H41F . . 109.5 ?
H41E C41A H41F . . 109.5 ?
C39 C42A H42D . . 109.5 ?
C39 C42A H42E . . 109.5 ?
H42D C42A H42E . . 109.5 ?
C39 C42A H42F . . 109.5 ?
H42D C42A H42F . . 109.5 ?
H42E C42A H42F . . 109.5 ?
C44 C43 C48 . . 118.4(3) ?
C44 C43 C35 . . 122.9(3) ?
C48 C43 C35 . . 118.8(3) ?
C45 C44 C43 . . 121.3(3) ?
C45 C44 H44 . . 119.3 ?
C43 C44 H44 . . 119.3 ?
C44 C45 C46 . . 120.1(3) ?
C44 C45 H45 . . 120.0 ?
C46 C45 H45 . . 120.0 ?
C45 C46 C47 . . 119.5(3) ?
C45 C46 H46 . . 120.3 ?
C47 C46 H46 . . 120.3 ?
C46 C47 C48 . . 120.9(3) ?
C46 C47 H47 . . 119.6 ?
C48 C47 H47 . . 119.6 ?
C47 C48 C43 . . 119.9(3) ?
C47 C48 C49 . . 120.8(3) ?
C43 C48 C49 . . 119.4(3) ?
N2 C49 C48 . . 111.8(3) ?
N2 C49 C50 . . 104.2(3) ?
C48 C49 C50 . . 115.7(3) ?
N2 C49 H49 . . 108.3 ?
C48 C49 H49 . . 108.3 ?
C50 C49 H49 . . 108.3 ?
C51 C50 C49 . . 115.7(3) ?
C51 C50 C25 . . 120.2(3) ?
C49 C50 C25 . . 103.3(2) ?
C51 C50 H50 . . 105.5 ?
C49 C50 H50 . . 105.5 ?
C25 C50 H50 . . 105.5 ?
C52 C51 C56 . . 117.3(3) ?
C52 C51 C50 . . 118.3(3) ?
C56 C51 C50 . . 124.4(3) ?
C53 C52 C51 . . 122.3(3) ?
C53 C52 H52 . . 118.9 ?
C51 C52 H52 . . 118.9 ?
C52 C53 C54 . . 120.2(3) ?
C52 C53 H53 . . 119.9 ?
C54 C53 H53 . . 119.9 ?
C55 C54 C53 . . 119.2(3) ?
C55 C54 H54 . . 120.4 ?
C53 C54 H54 . . 120.4 ?
C54 C55 C56 . . 121.2(3) ?
C54 C55 H55 . . 119.4 ?
C56 C55 H55 . . 119.4 ?
C55 C56 C51 . . 119.8(3) ?
C55 C56 C57 . . 116.8(3) ?
C51 C56 C57 . . 123.4(3) ?
C58 C57 C18 . . 108.6(3) ?
C58 C57 C56 . . 127.3(3) ?
C18 C57 C56 . . 123.5(3) ?
C57 C58 N1 . . 106.2(3) ?
C57 C58 C59 . . 135.4(3) ?
N1 C58 C59 . . 118.3(3) ?
C60 C59 C64 . . 118.6(3) ?
C60 C59 C58 . . 121.8(3) ?
C64 C59 C58 . . 119.5(3) ?
C61 C60 C59 . . 120.6(3) ?
C61 C60 H60 . . 119.7 ?
C59 C60 H60 . . 119.7 ?
C60 C61 C62 . . 120.9(3) ?
C60 C61 H61 . . 119.5 ?
C62 C61 H61 . . 119.5 ?
C63 C62 C61 . . 119.3(3) ?
C63 C62 H62 . . 120.3 ?
C61 C62 H62 . . 120.3 ?
C62 C63 C64 . . 121.8(3) ?
C62 C63 H63 . . 119.1 ?
C64 C63 H63 . . 119.1 ?
C63 C64 C59 . . 118.7(3) ?
C63 C64 C7 . . 121.9(3) ?
C59 C64 C7 . . 119.4(3) ?
Cl2 C65 Cl1 . . 111.3(3) ?
Cl2 C65 H65A . . 109.4 ?
Cl1 C65 H65A . . 109.4 ?
Cl2 C65 H65B . . 109.4 ?
Cl1 C65 H65B . . 109.4 ?
H65A C65 H65B . . 108.0 ?
C17 N1 C58 . . 111.2(3) ?
C17 N1 C8 . . 125.1(3) ?
C58 N1 C8 . . 123.7(3) ?
C34 N2 C26 . . 114.9(3) ?
C34 N2 C49 . . 114.9(3) ?
C26 N2 C49 . . 102.3(3) ?
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
C1 C2 . 1.530(5) ?
C1 C4 . 1.534(5) ?
C1 C5 . 1.534(5) ?
C1 C3 . 1.539(5) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 C6 . 1.386(5) ?
C5 C10 . 1.393(5) ?
C6 C7 . 1.400(5) ?
C6 H6 . 0.95 ?
C7 C8 . 1.399(5) ?
C7 C64 . 1.466(5) ?
C8 N1 . 1.390(4) ?
C8 C9 . 1.413(5) ?
C9 C10 . 1.394(5) ?
C9 C11 . 1.467(5) ?
C10 H10 . 0.95 ?
C11 C12 . 1.399(5) ?
C11 C16 . 1.418(5) ?
C12 C13 . 1.366(5) ?
C12 H12 . 0.95 ?
C13 C14 . 1.392(5) ?
C13 H13 . 0.95 ?
C14 C15 . 1.378(5) ?
C14 H14 . 0.95 ?
C15 C16 . 1.401(5) ?
C15 H15 . 0.95 ?
C16 C17 . 1.448(4) ?
C17 N1 . 1.385(4) ?
C17 C18 . 1.400(5) ?
C18 C57 . 1.416(5) ?
C18 C19 . 1.484(5) ?
C19 C20 . 1.402(5) ?
C19 C24 . 1.406(5) ?
C20 C21 . 1.380(5) ?
C20 H20 . 0.95 ?
C21 C22 . 1.383(5) ?
C21 H21 . 0.95 ?
C22 C23 . 1.377(5) ?
C22 H22 . 0.95 ?
C23 C24 . 1.404(5) ?
C23 H23 . 0.95 ?
C24 C25 . 1.507(5) ?
C25 C50 . 1.572(4) ?
C25 C26 . 1.572(5) ?
C25 H25 . 1.0 ?
C26 N2 . 1.461(4) ?
C26 C27 . 1.503(4) ?
C26 H26 . 1.0 ?
C27 C28 . 1.392(5) ?
C27 C32 . 1.400(5) ?
C28 C29 . 1.392(5) ?
C28 H28 . 0.95 ?
C29 C30 . 1.386(6) ?
C29 H29 . 0.95 ?
C30 C31 . 1.365(6) ?
C30 H30 . 0.95 ?
C31 C32 . 1.409(5) ?
C31 H31 . 0.95 ?
C32 C33 . 1.467(5) ?
C33 C38 . 1.383(5) ?
C33 C34 . 1.419(5) ?
C34 C35 . 1.401(5) ?
C34 N2 . 1.418(4) ?
C35 C36 . 1.396(5) ?
C35 C43 . 1.481(5) ?
C36 C37 . 1.393(5) ?
C36 H36 . 0.95 ?
C37 C38 . 1.403(5) ?
C37 C39 . 1.540(5) ?
C38 H38 . 0.95 ?
C39 C41 . 1.522(6) ?
C39 C42A . 1.530(12) ?
C39 C40 . 1.534(6) ?
C39 C40A . 1.534(13) ?
C39 C42 . 1.562(6) ?
C39 C41A . 1.572(12) ?
C40 H40A . 0.98 ?
C40 H40B . 0.98 ?
C40 H40C . 0.98 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
C40A H40D . 0.98 ?
C40A H40E . 0.98 ?
C40A H40F . 0.98 ?
C41A H41D . 0.98 ?
C41A H41E . 0.98 ?
C41A H41F . 0.98 ?
C42A H42D . 0.98 ?
C42A H42E . 0.98 ?
C42A H42F . 0.98 ?
C43 C44 . 1.394(5) ?
C43 C48 . 1.397(5) ?
C44 C45 . 1.379(5) ?
C44 H44 . 0.95 ?
C45 C46 . 1.379(5) ?
C45 H45 . 0.95 ?
C46 C47 . 1.384(5) ?
C46 H46 . 0.95 ?
C47 C48 . 1.389(5) ?
C47 H47 . 0.95 ?
C48 C49 . 1.504(5) ?
C49 N2 . 1.472(4) ?
C49 C50 . 1.559(5) ?
C49 H49 . 1.0 ?
C50 C51 . 1.512(5) ?
C50 H50 . 1.0 ?
C51 C52 . 1.399(5) ?
C51 C56 . 1.404(5) ?
C52 C53 . 1.375(5) ?
C52 H52 . 0.95 ?
C53 C54 . 1.381(5) ?
C53 H53 . 0.95 ?
C54 C55 . 1.379(5) ?
C54 H54 . 0.95 ?
C55 C56 . 1.404(5) ?
C55 H55 . 0.95 ?
C56 C57 . 1.491(4) ?
C57 C58 . 1.387(5) ?
C58 N1 . 1.387(4) ?
C58 C59 . 1.446(5) ?
C59 C60 . 1.412(5) ?
C59 C64 . 1.422(5) ?
C60 C61 . 1.375(5) ?
C60 H60 . 0.95 ?
C61 C62 . 1.387(5) ?
C61 H61 . 0.95 ?
C62 C63 . 1.379(5) ?
C62 H62 . 0.95 ?
C63 C64 . 1.398(5) ?
C63 H63 . 0.95 ?
C65 Cl2 . 1.749(4) ?
C65 Cl1 . 1.779(5) ?
C65 H65A . 0.99 ?
C65 H65B . 0.99 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336441
