#------------------------------------------------------------------------------
#$Date: 2022-04-03 23:08:27 +0300 (Sun, 03 Apr 2022) $
#$Revision: 274250 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519394.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_4519394
loop_
_publ_author_name
'Ulč, Jan'
'Asanuma, Yuya'
'Moss, Robert'
'Manca, Gabriele'
'Císařová, Ivana'
'Kotora, Martin'
_publ_section_title
;
 Computational, Mechanistic, and Experimental Insights into Regioselective
 Catalytic C-C Bond Activation in Linear 1-Aza-[3]triphenylene.
;
_journal_issue                   10
_journal_name_full               'ACS omega'
_journal_page_first              8665
_journal_page_last               8674
_journal_paper_doi               10.1021/acsomega.1c06664
_journal_volume                  7
_journal_year                    2022
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C59 H38 N, B F4, C H2 Cl2'
_chemical_formula_sum            'C60 H40 B Cl2 F4 N'
_chemical_formula_weight         932.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 97.0130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5453(3)
_cell_length_b                   22.0815(7)
_cell_length_c                   24.6638(8)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.1540
_cell_measurement_theta_min      2.6949
_cell_volume                     4619.1(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.12'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            60060
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.147
_diffrn_reflns_theta_min         2.695
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.741
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       prism
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.572
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.043
_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     613
_refine_ls_number_reflns         9061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0431
_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)+(0.0448P)²+3.4659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8875
_reflns_number_total             9061
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c06664_si_004.cif
_cod_data_source_block           cu_ju_834_p_b_kotora
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4519394
_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   0.436
_shelx_estimated_absorpt_t_max   0.714
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N1 N 0.52409(14) 0.30682(5) 0.62454(5) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.41934(17) 0.27793(7) 0.58661(6) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.424077 0.285094 0.548865 0.027 Uiso 1 1 calc R U . . .
C3 C 0.30850(18) 0.23915(7) 0.60186(6) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.237768 0.219304 0.574868 0.029 Uiso 1 1 calc R U . . .
C4 C 0.29909(17) 0.22869(7) 0.65689(6) 0.0234(3) Uani 1 1 d . . . . .
H4 H 0.218633 0.203226 0.667575 0.028 Uiso 1 1 calc R U . . .
C5 C 0.40762(16) 0.25553(6) 0.69645(6) 0.0201(3) Uani 1 1 d . . . . .
C6 C 0.40707(16) 0.24343(6) 0.75430(6) 0.0200(3) Uani 1 1 d . . . . .
C7 C 0.52217(16) 0.26673(6) 0.79167(6) 0.0202(3) Uani 1 1 d . . . . .
C8 C 0.64194(16) 0.30638(6) 0.77442(6) 0.0195(3) Uani 1 1 d . . . . .
C9 C 0.75222(17) 0.33495(7) 0.81187(6) 0.0209(3) Uani 1 1 d . . . . .
H9 H 0.741754 0.332187 0.849692 0.025 Uiso 1 1 calc R U . . .
C10 C 0.87860(16) 0.36777(6) 0.79537(6) 0.0200(3) Uani 1 1 d . . . . .
C11 C 0.99285(17) 0.39679(7) 0.83579(6) 0.0218(3) Uani 1 1 d . . . . .
C12 C 1.11673(17) 0.42800(7) 0.81956(6) 0.0226(3) Uani 1 1 d . . . . .
C13 C 1.15159(17) 0.42306(7) 0.76372(6) 0.0217(3) Uani 1 1 d . . . . .
C14 C 1.29707(17) 0.44321(7) 0.74854(6) 0.0260(3) Uani 1 1 d . . . . .
H14 H 1.366894 0.465709 0.773884 0.031 Uiso 1 1 calc R U . . .
C15 C 1.33909(18) 0.43072(7) 0.69763(7) 0.0268(3) Uani 1 1 d . . . . .
H15 H 1.435412 0.445871 0.687474 0.032 Uiso 1 1 calc R U . . .
C16 C 1.23944(18) 0.39557(7) 0.66074(6) 0.0251(3) Uani 1 1 d . . . . .
H16 H 1.271103 0.385122 0.626339 0.030 Uiso 1 1 calc R U . . .
C17 C 1.09608(17) 0.37614(7) 0.67410(6) 0.0218(3) Uani 1 1 d . . . . .
H17 H 1.030509 0.351562 0.649166 0.026 Uiso 1 1 calc R U . . .
C18 C 1.04564(16) 0.39233(6) 0.72435(6) 0.0197(3) Uani 1 1 d . . . . .
C19 C 0.89420(16) 0.37306(6) 0.73890(6) 0.0190(3) Uani 1 1 d . . . . .
C20 C 0.76318(16) 0.35653(6) 0.70011(6) 0.0185(3) Uani 1 1 d . . . . .
C21 C 0.64424(16) 0.31945(6) 0.71765(6) 0.0187(3) Uani 1 1 d . . . . .
C22 C 0.52529(16) 0.29408(6) 0.67947(6) 0.0187(3) Uani 1 1 d . . . . .
C23 C 0.62163(16) 0.35335(7) 0.60762(6) 0.0195(3) Uani 1 1 d . . . . .
C24 C 0.73481(16) 0.37904(7) 0.64410(6) 0.0194(3) Uani 1 1 d . . . . .
C25 C 0.27874(17) 0.20402(7) 0.77067(6) 0.0213(3) Uani 1 1 d . . . . .
C26 C 0.30760(19) 0.14441(7) 0.78702(7) 0.0291(3) Uani 1 1 d . . . . .
H26 H 0.411420 0.128481 0.789016 0.035 Uiso 1 1 calc R U . . .
C27 C 0.1858(2) 0.10808(8) 0.80044(7) 0.0355(4) Uani 1 1 d . . . . .
H27 H 0.206448 0.067372 0.811553 0.043 Uiso 1 1 calc R U . . .
C28 C 0.0346(2) 0.13087(9) 0.79771(7) 0.0349(4) Uani 1 1 d . . . . .
H28 H -0.048839 0.105894 0.806880 0.042 Uiso 1 1 calc R U . . .
C29 C 0.0049(2) 0.19012(9) 0.78159(7) 0.0355(4) Uani 1 1 d . . . . .
H29 H -0.099028 0.205912 0.779710 0.043 Uiso 1 1 calc R U . . .
C30 C 0.12648(19) 0.22656(8) 0.76817(7) 0.0297(3) Uani 1 1 d . . . . .
H30 H 0.105414 0.267283 0.757176 0.036 Uiso 1 1 calc R U . . .
C31 C 0.53033(17) 0.25154(7) 0.85101(6) 0.0211(3) Uani 1 1 d . . . . .
C32 C 0.41403(19) 0.27079(7) 0.88202(6) 0.0271(3) Uani 1 1 d . . . . .
H32 H 0.326368 0.293220 0.865199 0.033 Uiso 1 1 calc R U . . .
C33 C 0.4254(2) 0.25743(9) 0.93731(7) 0.0341(4) Uani 1 1 d . . . . .
H33 H 0.346565 0.271420 0.958307 0.041 Uiso 1 1 calc R U . . .
C34 C 0.5511(2) 0.22378(8) 0.96204(7) 0.0350(4) Uani 1 1 d . . . . .
H34 H 0.558127 0.214459 0.999867 0.042 Uiso 1 1 calc R U . . .
C35 C 0.6661(2) 0.20384(8) 0.93166(7) 0.0341(4) Uani 1 1 d . . . . .
H35 H 0.751847 0.180405 0.948464 0.041 Uiso 1 1 calc R U . . .
C36 C 0.65658(19) 0.21803(7) 0.87642(6) 0.0280(3) Uani 1 1 d . . . . .
H36 H 0.737028 0.204734 0.855806 0.034 Uiso 1 1 calc R U . . .
C37 C 0.97210(17) 0.39168(7) 0.89512(6) 0.0249(3) Uani 1 1 d . . . . .
C38 C 1.0160(2) 0.33788(9) 0.92262(7) 0.0359(4) Uani 1 1 d . . . . .
H38 H 1.053154 0.304743 0.903215 0.043 Uiso 1 1 calc R U . . .
C39 C 1.0056(2) 0.33255(11) 0.97809(8) 0.0471(5) Uani 1 1 d . . . . .
H39 H 1.038569 0.296255 0.996781 0.057 Uiso 1 1 calc R U . . .
C40 C 0.9471(3) 0.38025(11) 1.00638(7) 0.0494(5) Uani 1 1 d . . . . .
H40 H 0.940179 0.376676 1.044396 0.059 Uiso 1 1 calc R U . . .
C41 C 0.8993(3) 0.43257(11) 0.97916(8) 0.0497(5) Uani 1 1 d . . . . .
H41 H 0.856872 0.464831 0.998257 0.060 Uiso 1 1 calc R U . . .
C42 C 0.9127(2) 0.43861(9) 0.92354(7) 0.0378(4) Uani 1 1 d . . . . .
H42 H 0.880804 0.475190 0.905142 0.045 Uiso 1 1 calc R U . . .
C43 C 1.22659(18) 0.46502(7) 0.85828(6) 0.0243(3) Uani 1 1 d . . . . .
C44 C 1.2194(2) 0.52775(8) 0.85473(8) 0.0360(4) Uani 1 1 d . . . . .
H44 H 1.141106 0.546429 0.829533 0.043 Uiso 1 1 calc R U . . .
C45 C 1.3255(2) 0.56328(8) 0.88766(8) 0.0418(4) Uani 1 1 d . . . . .
H45 H 1.318890 0.606147 0.885096 0.050 Uiso 1 1 calc R U . . .
C46 C 1.4406(2) 0.53695(9) 0.92412(7) 0.0391(4) Uani 1 1 d . . . . .
H46 H 1.513895 0.561459 0.946392 0.047 Uiso 1 1 calc R U . . .
C47 C 1.4485(2) 0.47473(9) 0.92796(8) 0.0421(4) Uani 1 1 d . . . . .
H47 H 1.527823 0.456316 0.952959 0.051 Uiso 1 1 calc R U . . .
C48 C 1.3413(2) 0.43872(8) 0.89552(7) 0.0361(4) Uani 1 1 d . . . . .
H48 H 1.346688 0.395886 0.898896 0.043 Uiso 1 1 calc R U . . .
C49 C 0.81057(16) 0.43676(7) 0.62876(6) 0.0211(3) Uani 1 1 d . . . . .
C50 C 0.79183(17) 0.48793(7) 0.66044(6) 0.0243(3) Uani 1 1 d . . . . .
H50 H 0.730475 0.485397 0.689989 0.029 Uiso 1 1 calc R U . . .
C51 C 0.86164(19) 0.54246(8) 0.64934(7) 0.0314(4) Uani 1 1 d . . . . .
H51 H 0.846433 0.577151 0.670876 0.038 Uiso 1 1 calc R U . . .
C52 C 0.9535(2) 0.54654(8) 0.60697(7) 0.0357(4) Uani 1 1 d . . . . .
H52 H 1.002943 0.583696 0.599720 0.043 Uiso 1 1 calc R U . . .
C53 C 0.9724(2) 0.49611(9) 0.57536(7) 0.0348(4) Uani 1 1 d . . . . .
H53 H 1.035866 0.498754 0.546385 0.042 Uiso 1 1 calc R U . . .
C54 C 0.90013(18) 0.44154(8) 0.58529(6) 0.0273(3) Uani 1 1 d . . . . .
H54 H 0.911645 0.407543 0.562509 0.033 Uiso 1 1 calc R U . . .
C55 C 0.58285(17) 0.37382(7) 0.54961(6) 0.0215(3) Uani 1 1 d . . . . .
C56 C 0.6593(2) 0.34860(8) 0.50823(6) 0.0294(3) Uani 1 1 d . . . . .
H56 H 0.738290 0.318664 0.516737 0.035 Uiso 1 1 calc R U . . .
C57 C 0.6197(2) 0.36733(9) 0.45433(7) 0.0346(4) Uani 1 1 d . . . . .
H57 H 0.672898 0.350507 0.426207 0.042 Uiso 1 1 calc R U . . .
C58 C 0.5031(2) 0.41042(8) 0.44162(6) 0.0328(4) Uani 1 1 d . . . . .
H58 H 0.475923 0.422921 0.404822 0.039 Uiso 1 1 calc R U . . .
C59 C 0.42627(19) 0.43520(8) 0.48260(7) 0.0308(4) Uani 1 1 d . . . . .
H59 H 0.345919 0.464562 0.473827 0.037 Uiso 1 1 calc R U . . .
C60 C 0.46620(18) 0.41729(7) 0.53666(6) 0.0251(3) Uani 1 1 d . . . . .
H60 H 0.413853 0.434733 0.564708 0.030 Uiso 1 1 calc R U . . .
B1 B 0.8845(2) 0.22694(9) 0.60127(8) 0.0278(4) Uani 1 1 d . . . . .
F1 F 0.72856(12) 0.22053(6) 0.58123(5) 0.0514(3) Uani 1 1 d . . . . .
F2 F 0.96953(14) 0.17887(5) 0.58626(7) 0.0588(4) Uani 1 1 d . . . . .
F3 F 0.94386(12) 0.28059(4) 0.58151(4) 0.0345(2) Uani 1 1 d . . . . .
F4 F 0.89775(19) 0.23173(7) 0.65758(5) 0.0676(4) Uani 1 1 d . . . . .
C1S C 0.7916(2) 0.09394(9) 0.67345(8) 0.0392(4) Uani 1 1 d . . . . .
H1SA H 0.764243 0.094423 0.633273 0.047 Uiso 1 1 calc R U . . .
H1SB H 0.891689 0.116410 0.682401 0.047 Uiso 1 1 calc R U . . .
Cl1S Cl 0.64090(6) 0.12995(3) 0.70450(3) 0.05519(15) Uani 1 1 d . . . . .
Cl2S Cl 0.81704(6) 0.01846(2) 0.69618(2) 0.04358(12) 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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 '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'
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 N1 C22 120.02(13) . . ?
C2 N1 C23 119.65(12) . . ?
C22 N1 C23 120.11(12) . . ?
C3 C2 N1 121.45(13) . . ?
C3 C2 H2 119.3 . . ?
N1 C2 H2 119.3 . . ?
C2 C3 C4 119.95(14) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.03(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C22 118.91(13) . . ?
C4 C5 C6 121.86(13) . . ?
C22 C5 C6 119.19(13) . . ?
C7 C6 C5 120.41(13) . . ?
C7 C6 C25 121.98(13) . . ?
C5 C6 C25 117.61(12) . . ?
C6 C7 C8 120.40(13) . . ?
C6 C7 C31 121.38(13) . . ?
C8 C7 C31 118.21(12) . . ?
C9 C8 C21 118.02(13) . . ?
C9 C8 C7 121.70(13) . . ?
C21 C8 C7 120.21(13) . . ?
C8 C9 C10 121.76(13) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C19 119.68(13) . . ?
C9 C10 C11 120.31(13) . . ?
C19 C10 C11 120.00(13) . . ?
C12 C11 C10 120.06(13) . . ?
C12 C11 C37 120.87(13) . . ?
C10 C11 C37 119.06(13) . . ?
C11 C12 C13 119.89(13) . . ?
C11 C12 C43 122.50(13) . . ?
C13 C12 C43 117.50(13) . . ?
C14 C13 C18 118.58(14) . . ?
C14 C13 C12 121.19(13) . . ?
C18 C13 C12 119.95(13) . . ?
C15 C14 C13 120.98(14) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.85(14) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.36(14) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.61(14) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.10(13) . . ?
C17 C18 C19 121.50(13) . . ?
C13 C18 C19 119.11(13) . . ?
C10 C19 C20 118.43(13) . . ?
C10 C19 C18 117.44(13) . . ?
C20 C19 C18 124.07(13) . . ?
C21 C20 C19 118.51(12) . . ?
C21 C20 C24 116.37(12) . . ?
C19 C20 C24 124.93(13) . . ?
C20 C21 C22 120.73(13) . . ?
C20 C21 C8 120.80(13) . . ?
C22 C21 C8 118.46(13) . . ?
N1 C22 C21 119.38(13) . . ?
N1 C22 C5 119.37(12) . . ?
C21 C22 C5 121.25(13) . . ?
C24 C23 N1 120.20(12) . . ?
C24 C23 C55 124.17(13) . . ?
N1 C23 C55 115.49(12) . . ?
C23 C24 C20 120.38(13) . . ?
C23 C24 C49 118.77(13) . . ?
C20 C24 C49 120.08(12) . . ?
C30 C25 C26 119.01(14) . . ?
C30 C25 C6 119.63(14) . . ?
C26 C25 C6 121.34(13) . . ?
C27 C26 C25 120.38(15) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C26 120.21(16) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 119.78(16) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C30 120.14(16) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 120.49(16) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C32 C31 C36 118.74(14) . . ?
C32 C31 C7 121.21(13) . . ?
C36 C31 C7 120.05(13) . . ?
C33 C32 C31 120.40(15) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 120.30(16) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 119.86(15) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.03(16) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 120.66(15) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C42 C37 C38 119.02(15) . . ?
C42 C37 C11 122.21(15) . . ?
C38 C37 C11 118.77(15) . . ?
C39 C38 C37 120.37(19) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C38 C39 C40 120.08(19) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C41 C40 C39 119.74(17) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C40 C41 C42 120.4(2) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C37 C42 C41 120.38(18) . . ?
C37 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C48 C43 C44 118.80(15) . . ?
C48 C43 C12 122.09(14) . . ?
C44 C43 C12 119.00(14) . . ?
C45 C44 C43 120.49(17) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C46 C45 C44 120.54(17) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C45 C46 C47 119.37(16) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C46 C47 C48 120.49(17) . . ?
C46 C47 H47 119.8 . . ?
C48 C47 H47 119.8 . . ?
C43 C48 C47 120.30(17) . . ?
C43 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
C50 C49 C54 118.72(14) . . ?
C50 C49 C24 117.72(13) . . ?
C54 C49 C24 123.55(14) . . ?
C51 C50 C49 120.79(15) . . ?
C51 C50 H50 119.6 . . ?
C49 C50 H50 119.6 . . ?
C52 C51 C50 120.20(16) . . ?
C52 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C53 C52 C51 119.38(16) . . ?
C53 C52 H52 120.3 . . ?
C51 C52 H52 120.3 . . ?
C52 C53 C54 120.97(16) . . ?
C52 C53 H53 119.5 . . ?
C54 C53 H53 119.5 . . ?
C53 C54 C49 119.90(16) . . ?
C53 C54 H54 120.0 . . ?
C49 C54 H54 120.0 . . ?
C60 C55 C56 119.59(14) . . ?
C60 C55 C23 119.71(13) . . ?
C56 C55 C23 120.68(13) . . ?
C55 C56 C57 119.97(15) . . ?
C55 C56 H56 120.0 . . ?
C57 C56 H56 120.0 . . ?
C58 C57 C56 120.22(16) . . ?
C58 C57 H57 119.9 . . ?
C56 C57 H57 119.9 . . ?
C59 C58 C57 119.91(15) . . ?
C59 C58 H58 120.0 . . ?
C57 C58 H58 120.0 . . ?
C58 C59 C60 120.30(15) . . ?
C58 C59 H59 119.8 . . ?
C60 C59 H59 119.8 . . ?
C59 C60 C55 120.01(15) . . ?
C59 C60 H60 120.0 . . ?
C55 C60 H60 120.0 . . ?
F2 B1 F1 110.40(15) . . ?
F2 B1 F4 110.58(16) . . ?
F1 B1 F4 109.04(16) . . ?
F2 B1 F3 109.70(14) . . ?
F1 B1 F3 109.83(14) . . ?
F4 B1 F3 107.23(14) . . ?
Cl2S C1S Cl1S 110.84(10) . . ?
Cl2S C1S H1SA 109.5 . . ?
Cl1S C1S H1SA 109.5 . . ?
Cl2S C1S H1SB 109.5 . . ?
Cl1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 108.1 . . ?
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
N1 C2 1.3706(18) . ?
N1 C22 1.3825(18) . ?
N1 C23 1.4177(19) . ?
C2 C3 1.363(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(2) . ?
C4 H4 0.9500 . ?
C5 C22 1.419(2) . ?
C5 C6 1.452(2) . ?
C6 C7 1.364(2) . ?
C6 C25 1.494(2) . ?
C7 C8 1.450(2) . ?
C7 C31 1.4947(19) . ?
C8 C9 1.388(2) . ?
C8 C21 1.4321(19) . ?
C9 C10 1.402(2) . ?
C9 H9 0.9500 . ?
C10 C19 1.420(2) . ?
C10 C11 1.456(2) . ?
C11 C12 1.364(2) . ?
C11 C37 1.500(2) . ?
C12 C13 1.448(2) . ?
C12 C43 1.498(2) . ?
C13 C14 1.413(2) . ?
C13 C18 1.417(2) . ?
C14 C15 1.376(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.407(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.448(2) . ?
C19 C20 1.4284(19) . ?
C20 C21 1.413(2) . ?
C20 C24 1.4604(19) . ?
C21 C22 1.4141(19) . ?
C23 C24 1.362(2) . ?
C23 C55 1.4982(19) . ?
C24 C49 1.499(2) . ?
C25 C30 1.387(2) . ?
C25 C26 1.390(2) . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.382(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.392(2) . ?
C31 C36 1.392(2) . ?
C32 C33 1.387(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.385(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.391(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C42 1.382(2) . ?
C37 C38 1.396(2) . ?
C38 C39 1.387(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.390(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.373(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.397(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C48 1.387(2) . ?
C43 C44 1.389(2) . ?
C44 C45 1.385(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.378(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.378(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.390(2) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C50 1.394(2) . ?
C49 C54 1.395(2) . ?
C50 C51 1.386(2) . ?
C50 H50 0.9500 . ?
C51 C52 1.384(3) . ?
C51 H51 0.9500 . ?
C52 C53 1.380(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.389(2) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 C60 1.393(2) . ?
C55 C56 1.393(2) . ?
C56 C57 1.394(2) . ?
C56 H56 0.9500 . ?
C57 C58 1.386(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.383(3) . ?
C58 H58 0.9500 . ?
C59 C60 1.393(2) . ?
C59 H59 0.9500 . ?
C60 H60 0.9500 . ?
B1 F2 1.363(2) . ?
B1 F1 1.371(2) . ?
B1 F4 1.384(2) . ?
B1 F3 1.400(2) . ?
C1S Cl2S 1.7634(19) . ?
C1S Cl1S 1.7659(19) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
