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#$Date: 2024-07-05 19:04:12 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293020 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/59/7715979.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_7715979
loop_
_publ_author_name
'Zender, Elena'
'Valverde, Danillo'
'Neubaur, Robert'
'Karger, Sebastian'
'Virovets, Alexander'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Olivier, Yoann'
'Wagner, Matthias'
_publ_section_title
;
 Borylation and rearrangement reactions of azasilaanthracenes to afford
 B,N-doped nanographenes.
;
_journal_issue                   22
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9294
_journal_page_last               9300
_journal_paper_doi               10.1039/d4dt01166j
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C51 H36 B3 N3, 2(C H Cl3)'
_chemical_formula_sum            'C53 H38 B3 Cl6 N3'
_chemical_formula_weight         961.99
_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
;
2024-05-06 deposited with the CCDC.	2024-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                114.175(8)
_cell_angle_beta                 101.129(6)
_cell_angle_gamma                103.186(7)
_cell_formula_units_Z            2
_cell_length_a                   12.7063(9)
_cell_length_b                   13.7794(11)
_cell_length_c                   15.4494(12)
_cell_measurement_reflns_used    601
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0580
_cell_measurement_theta_min      4.1560
_cell_volume                     2274.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_computing_data_collection       'P24 beamline local software'
_computing_data_reduction        'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_computing_publication_material  'IUCr online tools'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector
'X-Spectrum Lambda 7.5M CdTe photon-counting detector'
_diffrn_detector_area_resol_mean 18.2
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device
'DESY Petra3 P24 beamline, Huber diffractometer, Lambda 7.5M CdTe'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.500
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46742
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        17.458
_diffrn_reflns_theta_max         17.977
_diffrn_reflns_theta_min         1.869
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.43a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brownish-yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       'elongated prism'
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.211
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         8606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0799
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1642P)²+1.8586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2399
_refine_ls_wR_factor_ref         0.2472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7127
_reflns_number_total             8606
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt01166j3.cif
_cod_data_source_block           wa3400-P24
_cod_depositor_comments
'Adding full bibliography for 7715973--7715981.cif.'
_cod_original_cell_volume        2274.3(3)
_cod_database_code               7715979
_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   0.939
_shelx_estimated_absorpt_t_max   0.992
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
B1 B 0.7442(3) 0.2867(3) 0.6962(2) 0.0298(6) Uani 1 1 d . . . . .
B2 B 0.4294(2) 0.3740(2) 0.8347(2) 0.0255(6) Uani 1 1 d . . . . .
B3 B 0.5905(3) 0.5829(2) 0.6580(2) 0.0283(6) Uani 1 1 d . . . . .
N1 N 0.58622(18) 0.41481(18) 0.72744(16) 0.0237(4) Uani 1 1 d . . . . .
N2 N 0.32714(19) 0.54258(18) 0.90797(17) 0.0266(5) Uani 1 1 d . . . . .
N3 N 0.4491(2) 0.7152(2) 0.71531(19) 0.0327(5) Uani 1 1 d . . . . .
C11 C 0.6315(2) 0.2433(2) 0.71056(19) 0.0276(5) Uani 1 1 d . . . . .
C12 C 0.5638(2) 0.3145(2) 0.73731(18) 0.0245(5) Uani 1 1 d . . . . .
C13 C 0.4764(2) 0.2834(2) 0.77555(19) 0.0244(5) Uani 1 1 d . . . . .
C14 C 0.4408(2) 0.1726(2) 0.7620(2) 0.0283(6) Uani 1 1 d . . . . .
H14 H 0.376081 0.148191 0.779800 0.034 Uiso 1 1 calc R U . . .
C15 C 0.4966(2) 0.0971(2) 0.7236(2) 0.0316(6) Uani 1 1 d . . . . .
H15 H 0.467928 0.020877 0.710717 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5950(2) 0.1365(2) 0.7048(2) 0.0312(6) Uani 1 1 d . . . . .
H16 H 0.639729 0.089280 0.687325 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7608(2) 0.3944(2) 0.6868(2) 0.0319(6) Uani 1 1 d . . . . .
C22 C 0.6762(2) 0.4460(2) 0.6907(2) 0.0274(5) Uani 1 1 d . . . . .
C23 C 0.6834(2) 0.5289(2) 0.6581(2) 0.0310(6) Uani 1 1 d . . . . .
C24 C 0.7821(3) 0.5671(3) 0.6364(3) 0.0401(7) Uani 1 1 d . . . . .
H24 H 0.788868 0.625016 0.617345 0.048 Uiso 1 1 calc R U . . .
C25 C 0.8699(3) 0.5240(3) 0.6416(3) 0.0485(8) Uani 1 1 d . . . . .
H25 H 0.937559 0.554363 0.630008 0.058 Uiso 1 1 calc R U . . .
C26 C 0.8569(3) 0.4371(3) 0.6636(3) 0.0429(7) Uani 1 1 d . . . . .
H26 H 0.914780 0.403864 0.663275 0.051 Uiso 1 1 calc R U . . .
C31 C 0.3646(2) 0.3761(2) 0.90956(19) 0.0261(5) Uani 1 1 d . . . . .
C32 C 0.3160(2) 0.4624(2) 0.94290(19) 0.0251(5) Uani 1 1 d . . . . .
C33 C 0.2560(2) 0.4694(2) 1.0116(2) 0.0292(6) Uani 1 1 d . . . . .
H33 H 0.223743 0.527407 1.033359 0.035 Uiso 1 1 calc R U . . .
C34 C 0.2441(2) 0.3922(2) 1.0472(2) 0.0322(6) Uani 1 1 d . . . . .
H34 H 0.201538 0.395879 1.091993 0.039 Uiso 1 1 calc R U . . .
C35 C 0.2939(3) 0.3086(2) 1.0183(2) 0.0349(6) Uani 1 1 d . . . . .
H35 H 0.286631 0.256376 1.044023 0.042 Uiso 1 1 calc R U . . .
C36 C 0.3537(2) 0.3027(2) 0.9517(2) 0.0303(6) Uani 1 1 d . . . . .
H36 H 0.388944 0.246771 0.933667 0.036 Uiso 1 1 calc R U . . .
C41 C 0.4496(2) 0.4723(2) 0.81336(19) 0.0254(5) Uani 1 1 d . . . . .
C42 C 0.3917(2) 0.5511(2) 0.8469(2) 0.0266(5) Uani 1 1 d . . . . .
C43 C 0.3946(2) 0.6339(2) 0.8173(2) 0.0313(6) Uani 1 1 d . . . . .
H43 H 0.357071 0.686721 0.841775 0.038 Uiso 1 1 calc R U . . .
C44 C 0.4532(2) 0.6379(2) 0.7514(2) 0.0292(6) Uani 1 1 d . . . . .
C45 C 0.5196(2) 0.5669(2) 0.72070(19) 0.0262(5) Uani 1 1 d . . . . .
C46 C 0.5178(2) 0.4856(2) 0.75429(19) 0.0244(5) Uani 1 1 d . . . . .
C51 C 0.5685(2) 0.6580(2) 0.6095(2) 0.0310(6) Uani 1 1 d . . . . .
C52 C 0.4981(2) 0.7222(2) 0.6430(2) 0.0315(6) Uani 1 1 d . . . . .
C53 C 0.4759(3) 0.7939(2) 0.6034(2) 0.0360(6) Uani 1 1 d . . . . .
H53 H 0.427539 0.835579 0.624989 0.043 Uiso 1 1 calc R U . . .
C54 C 0.5237(3) 0.8036(3) 0.5337(2) 0.0394(7) Uani 1 1 d . . . . .
H54 H 0.510471 0.854240 0.509259 0.047 Uiso 1 1 calc R U . . .
C55 C 0.5915(3) 0.7403(3) 0.4984(2) 0.0382(7) Uani 1 1 d . . . . .
H55 H 0.623704 0.746814 0.449582 0.046 Uiso 1 1 calc R U . . .
C56 C 0.6113(3) 0.6680(3) 0.5352(2) 0.0355(6) Uani 1 1 d . . . . .
H56 H 0.655548 0.623142 0.509128 0.043 Uiso 1 1 calc R U . . .
C61 C 0.8391(2) 0.2295(2) 0.6929(2) 0.0303(6) Uani 1 1 d . . . . .
C62 C 0.9328(2) 0.2745(2) 0.7800(2) 0.0300(6) Uani 1 1 d . . . . .
C63 C 1.0210(3) 0.2310(3) 0.7793(2) 0.0350(6) Uani 1 1 d . . . . .
H63 H 1.083372 0.262367 0.839083 0.042 Uiso 1 1 calc R U . . .
C64 C 1.0199(3) 0.1418(3) 0.6922(2) 0.0385(7) Uani 1 1 d . . . . .
C65 C 0.9270(3) 0.0965(3) 0.6062(2) 0.0393(7) Uani 1 1 d . . . . .
H65 H 0.924707 0.035205 0.546589 0.047 Uiso 1 1 calc R U . . .
C66 C 0.8368(3) 0.1386(3) 0.6049(2) 0.0351(6) Uani 1 1 d . . . . .
C67 C 0.9367(3) 0.3695(3) 0.8774(2) 0.0351(6) Uani 1 1 d . . . . .
H67A H 0.871137 0.343707 0.896898 0.053 Uiso 1 1 calc R U . . .
H67B H 0.933927 0.435121 0.868032 0.053 Uiso 1 1 calc R U . . .
H67C H 1.007590 0.390873 0.930131 0.053 Uiso 1 1 calc R U . . .
C68 C 1.1179(3) 0.0972(3) 0.6934(3) 0.0544(10) Uani 1 1 d . . . . .
H68A H 1.181401 0.146843 0.687065 0.082 Uiso 1 1 calc R U . . .
H68B H 1.092937 0.020535 0.637191 0.082 Uiso 1 1 calc R U . . .
H68C H 1.143117 0.095406 0.756599 0.082 Uiso 1 1 calc R U . . .
C69 C 0.7382(3) 0.0871(3) 0.5086(2) 0.0482(8) Uani 1 1 d . . . . .
H69A H 0.761661 0.114799 0.463642 0.072 Uiso 1 1 calc R U . . .
H69B H 0.673074 0.108797 0.523774 0.072 Uiso 1 1 calc R U . . .
H69C H 0.716234 0.004423 0.475942 0.072 Uiso 1 1 calc R U . . .
C71 C 0.2635(2) 0.6196(2) 0.9340(2) 0.0273(5) Uani 1 1 d . . . . .
C72 C 0.1541(2) 0.5886(2) 0.8728(2) 0.0331(6) Uani 1 1 d . . . . .
H72 H 0.118507 0.515484 0.816152 0.040 Uiso 1 1 calc R U . . .
C73 C 0.0958(3) 0.6662(3) 0.8952(2) 0.0401(7) Uani 1 1 d . . . . .
H73 H 0.021027 0.646459 0.852802 0.048 Uiso 1 1 calc R U . . .
C74 C 0.1472(3) 0.7711(3) 0.9787(2) 0.0403(7) Uani 1 1 d . . . . .
H74 H 0.107249 0.823268 0.994035 0.048 Uiso 1 1 calc R U . . .
C75 C 0.2573(3) 0.8013(3) 1.0410(2) 0.0390(7) Uani 1 1 d . . . . .
H75 H 0.292271 0.873753 1.098488 0.047 Uiso 1 1 calc R U . . .
C76 C 0.3160(3) 0.7251(2) 1.0188(2) 0.0329(6) Uani 1 1 d . . . . .
H76 H 0.390906 0.744877 1.061049 0.039 Uiso 1 1 calc R U . . .
C81 C 0.3893(3) 0.7928(3) 0.7549(3) 0.0423(8) Uani 1 1 d . . . . .
C82 C 0.2736(4) 0.7610(4) 0.7105(4) 0.0718(13) Uani 1 1 d . . . . .
H82 H 0.231484 0.688891 0.653887 0.086 Uiso 1 1 calc R U . . .
C83 C 0.2200(5) 0.8399(6) 0.7524(6) 0.096(2) Uani 1 1 d . . . . .
H83 H 0.140288 0.820213 0.722857 0.115 Uiso 1 1 calc R U . . .
C84 C 0.2790(6) 0.9432(5) 0.8339(5) 0.0879(19) Uani 1 1 d . . . . .
H84 H 0.240506 0.994299 0.860583 0.106 Uiso 1 1 calc R U . . .
C85 C 0.3927(6) 0.9729(4) 0.8767(4) 0.0780(17) Uani 1 1 d . . . . .
H85 H 0.433791 1.045045 0.933466 0.094 Uiso 1 1 calc R U . . .
C86 C 0.4510(4) 0.8975(3) 0.8379(3) 0.0514(9) Uani 1 1 d . . . . .
H86 H 0.530731 0.918171 0.867986 0.062 Uiso 1 1 calc R U . . .
C1S C 0.8263(4) -0.1197(3) 0.7977(4) 0.0628(11) Uani 1 1 d . . . . .
H1S H 0.772135 -0.190777 0.737262 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl 0.84877(17) -0.01083(12) 0.76555(11) 0.0960(5) Uani 1 1 d . . . . .
Cl2 Cl 0.95229(13) -0.14341(14) 0.83454(14) 0.1069(6) Uani 1 1 d . . . . .
Cl3 Cl 0.76286(14) -0.08865(12) 0.89115(13) 0.0895(5) Uani 1 1 d . . . . .
C2S C 0.0751(4) 0.2959(3) 0.5513(3) 0.0560(9) Uani 1 1 d . . . . .
H2S H 0.010733 0.265076 0.571838 0.067 Uiso 0.55 1 calc R U P A 1
H2SA H 0.047206 0.268770 0.596510 0.067 Uiso 0.45 1 calc R U P B 2
Cl4 Cl 0.0820(4) 0.1899(5) 0.4443(3) 0.0668(10) Uani 0.55 1 d . . P C 1
Cl6 Cl 0.0607(4) 0.4077(3) 0.5343(3) 0.1151(14) Uani 0.55 1 d . . P C 1
Cl8 Cl 0.20949(17) 0.3472(2) 0.64798(14) 0.0740(6) Uani 0.55 1 d . . P C 1
Cl5 Cl -0.0464(3) 0.3026(4) 0.4687(2) 0.1011(12) Uani 0.45 1 d . . P C 2
Cl7 Cl 0.1712(3) 0.4280(2) 0.62141(19) 0.0897(11) Uani 0.45 1 d . . P C 2
Cl9 Cl 0.1189(6) 0.1977(6) 0.4731(6) 0.107(2) Uani 0.45 1 d . . P C 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0007 0.0007 '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 0.0003 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0019 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0817 0.0785 '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
C11 B1 C21 113.7(2) . . ?
C11 B1 C61 124.8(3) . . ?
C21 B1 C61 121.5(3) . . ?
C41 B2 C31 117.0(2) . . ?
C41 B2 C13 113.6(2) . . ?
C31 B2 C13 129.3(2) . . ?
C45 B3 C23 113.7(2) . . ?
C45 B3 C51 117.3(2) . . ?
C23 B3 C51 128.8(3) . . ?
C12 N1 C22 120.5(2) . . ?
C12 N1 C46 120.0(2) . . ?
C22 N1 C46 119.5(2) . . ?
C42 N2 C32 124.6(2) . . ?
C42 N2 C71 117.1(2) . . ?
C32 N2 C71 118.3(2) . . ?
C44 N3 C52 124.4(2) . . ?
C44 N3 C81 117.5(2) . . ?
C52 N3 C81 118.1(2) . . ?
C16 C11 C12 118.6(2) . . ?
C16 C11 B1 120.8(2) . . ?
C12 C11 B1 120.5(2) . . ?
C13 C12 N1 121.2(2) . . ?
C13 C12 C11 118.3(2) . . ?
N1 C12 C11 120.4(2) . . ?
C14 C13 C12 118.2(2) . . ?
C14 C13 B2 122.9(2) . . ?
C12 C13 B2 118.8(2) . . ?
C15 C14 C13 122.5(3) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C16 C15 C14 117.8(2) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C11 122.4(2) . . ?
C15 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?
C26 C21 C22 119.1(3) . . ?
C26 C21 B1 119.2(3) . . ?
C22 C21 B1 121.4(3) . . ?
C21 C22 C23 118.7(3) . . ?
C21 C22 N1 120.0(2) . . ?
C23 C22 N1 121.2(2) . . ?
C24 C23 C22 118.2(3) . . ?
C24 C23 B3 121.8(3) . . ?
C22 C23 B3 119.7(2) . . ?
C25 C24 C23 122.8(3) . . ?
C25 C24 H24 118.6 . . ?
C23 C24 H24 118.6 . . ?
C26 C25 C24 118.3(3) . . ?
C26 C25 H25 120.9 . . ?
C24 C25 H25 120.9 . . ?
C25 C26 C21 122.3(3) . . ?
C25 C26 H26 118.8 . . ?
C21 C26 H26 118.8 . . ?
C36 C31 C32 116.8(2) . . ?
C36 C31 B2 125.5(2) . . ?
C32 C31 B2 117.7(2) . . ?
N2 C32 C33 118.7(2) . . ?
N2 C32 C31 120.6(2) . . ?
C33 C32 C31 120.6(2) . . ?
C34 C33 C32 120.0(2) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.8(3) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 119.1(3) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C31 122.7(3) . . ?
C35 C36 H36 118.6 . . ?
C31 C36 H36 118.6 . . ?
C46 C41 C42 118.0(2) . . ?
C46 C41 B2 122.2(2) . . ?
C42 C41 B2 119.7(2) . . ?
N2 C42 C43 118.6(2) . . ?
N2 C42 C41 119.4(2) . . ?
C43 C42 C41 121.9(2) . . ?
C44 C43 C42 118.7(2) . . ?
C44 C43 H43 120.7 . . ?
C42 C43 H43 120.7 . . ?
C43 C44 N3 118.9(2) . . ?
C43 C44 C45 122.1(2) . . ?
N3 C44 C45 119.0(2) . . ?
C46 C45 C44 117.9(2) . . ?
C46 C45 B3 122.3(2) . . ?
C44 C45 B3 119.8(2) . . ?
C41 C46 C45 121.0(2) . . ?
C41 C46 N1 119.4(2) . . ?
C45 C46 N1 119.5(2) . . ?
C56 C51 C52 117.1(3) . . ?
C56 C51 B3 126.0(3) . . ?
C52 C51 B3 116.9(3) . . ?
N3 C52 C53 118.9(3) . . ?
N3 C52 C51 121.0(2) . . ?
C53 C52 C51 120.1(3) . . ?
C54 C53 C52 120.3(3) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C53 C54 C55 120.8(3) . . ?
C53 C54 H54 119.6 . . ?
C55 C54 H54 119.6 . . ?
C56 C55 C54 119.2(3) . . ?
C56 C55 H55 120.4 . . ?
C54 C55 H55 120.4 . . ?
C55 C56 C51 122.5(3) . . ?
C55 C56 H56 118.7 . . ?
C51 C56 H56 118.7 . . ?
C62 C61 C66 118.4(2) . . ?
C62 C61 B1 118.7(2) . . ?
C66 C61 B1 122.9(2) . . ?
C63 C62 C61 120.8(3) . . ?
C63 C62 C67 119.1(3) . . ?
C61 C62 C67 120.1(2) . . ?
C62 C63 C64 121.2(3) . . ?
C62 C63 H63 119.4 . . ?
C64 C63 H63 119.4 . . ?
C65 C64 C63 118.2(3) . . ?
C65 C64 C68 121.8(3) . . ?
C63 C64 C68 120.0(3) . . ?
C64 C65 C66 121.7(3) . . ?
C64 C65 H65 119.1 . . ?
C66 C65 H65 119.1 . . ?
C65 C66 C61 119.7(3) . . ?
C65 C66 C69 119.6(3) . . ?
C61 C66 C69 120.7(3) . . ?
C62 C67 H67A 109.5 . . ?
C62 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C62 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C64 C68 H68A 109.5 . . ?
C64 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C64 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C66 C69 H69A 109.5 . . ?
C66 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C66 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C72 C71 C76 121.3(2) . . ?
C72 C71 N2 119.6(2) . . ?
C76 C71 N2 119.1(2) . . ?
C71 C72 C73 119.2(3) . . ?
C71 C72 H72 120.4 . . ?
C73 C72 H72 120.4 . . ?
C74 C73 C72 120.0(3) . . ?
C74 C73 H73 120.0 . . ?
C72 C73 H73 120.0 . . ?
C73 C74 C75 120.4(3) . . ?
C73 C74 H74 119.8 . . ?
C75 C74 H74 119.8 . . ?
C76 C75 C74 119.9(3) . . ?
C76 C75 H75 120.0 . . ?
C74 C75 H75 120.0 . . ?
C71 C76 C75 119.1(3) . . ?
C71 C76 H76 120.4 . . ?
C75 C76 H76 120.4 . . ?
C82 C81 C86 121.7(3) . . ?
C82 C81 N3 119.8(3) . . ?
C86 C81 N3 118.6(3) . . ?
C81 C82 C83 117.2(5) . . ?
C81 C82 H82 121.4 . . ?
C83 C82 H82 121.4 . . ?
C84 C83 C82 122.1(6) . . ?
C84 C83 H83 119.0 . . ?
C82 C83 H83 119.0 . . ?
C85 C84 C83 119.8(4) . . ?
C85 C84 H84 120.1 . . ?
C83 C84 H84 120.1 . . ?
C84 C85 C86 120.7(5) . . ?
C84 C85 H85 119.7 . . ?
C86 C85 H85 119.7 . . ?
C81 C86 C85 118.6(5) . . ?
C81 C86 H86 120.7 . . ?
C85 C86 H86 120.7 . . ?
Cl3 C1S Cl2 111.1(3) . . ?
Cl3 C1S Cl1 109.5(2) . . ?
Cl2 C1S Cl1 111.9(3) . . ?
Cl3 C1S H1S 108.0 . . ?
Cl2 C1S H1S 108.0 . . ?
Cl1 C1S H1S 108.0 . . ?
Cl7 C2S Cl9 116.6(4) . . ?
Cl6 C2S Cl4 111.6(3) . . ?
Cl6 C2S Cl8 107.2(3) . . ?
Cl4 C2S Cl8 106.8(3) . . ?
Cl7 C2S Cl5 107.7(3) . . ?
Cl9 C2S Cl5 105.1(3) . . ?
Cl6 C2S H2S 110.4 . . ?
Cl4 C2S H2S 110.4 . . ?
Cl8 C2S H2S 110.4 . . ?
Cl7 C2S H2SA 109.1 . . ?
Cl9 C2S H2SA 109.1 . . ?
Cl5 C2S H2SA 109.1 . . ?
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
B1 C11 1.516(4) . ?
B1 C21 1.521(4) . ?
B1 C61 1.582(4) . ?
B2 C41 1.499(4) . ?
B2 C31 1.538(4) . ?
B2 C13 1.538(4) . ?
B3 C45 1.490(4) . ?
B3 C23 1.532(4) . ?
B3 C51 1.548(4) . ?
N1 C12 1.423(3) . ?
N1 C22 1.429(3) . ?
N1 C46 1.440(3) . ?
N2 C42 1.386(3) . ?
N2 C32 1.406(3) . ?
N2 C71 1.453(3) . ?
N3 C44 1.396(3) . ?
N3 C52 1.405(4) . ?
N3 C81 1.454(4) . ?
C11 C16 1.399(4) . ?
C11 C12 1.436(3) . ?
C12 C13 1.417(4) . ?
C13 C14 1.403(4) . ?
C14 C15 1.389(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.408(4) . ?
C21 C22 1.416(4) . ?
C22 C23 1.416(4) . ?
C23 C24 1.403(4) . ?
C24 C25 1.383(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.357(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.406(4) . ?
C31 C32 1.420(4) . ?
C32 C33 1.406(4) . ?
C33 C34 1.378(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.395(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.409(4) . ?
C41 C42 1.429(3) . ?
C42 C43 1.389(4) . ?
C43 C44 1.383(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.430(4) . ?
C45 C46 1.413(4) . ?
C51 C56 1.403(4) . ?
C51 C52 1.419(4) . ?
C52 C53 1.409(4) . ?
C53 C54 1.371(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.390(5) . ?
C54 H54 0.9500 . ?
C55 C56 1.379(4) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C62 1.405(4) . ?
C61 C66 1.411(4) . ?
C62 C63 1.387(4) . ?
C62 C67 1.519(4) . ?
C63 C64 1.396(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.389(4) . ?
C64 C68 1.509(4) . ?
C65 C66 1.399(4) . ?
C65 H65 0.9500 . ?
C66 C69 1.515(4) . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C71 C72 1.378(4) . ?
C71 C76 1.391(4) . ?
C72 C73 1.403(4) . ?
C72 H72 0.9500 . ?
C73 C74 1.377(5) . ?
C73 H73 0.9500 . ?
C74 C75 1.395(5) . ?
C74 H74 0.9500 . ?
C75 C76 1.391(4) . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
C81 C82 1.376(6) . ?
C81 C86 1.385(6) . ?
C82 C83 1.413(6) . ?
C82 H82 0.9500 . ?
C83 C84 1.362(10) . ?
C83 H83 0.9500 . ?
C84 C85 1.354(9) . ?
C84 H84 0.9500 . ?
C85 C86 1.414(5) . ?
C85 H85 0.9500 . ?
C86 H86 0.9500 . ?
C1S Cl3 1.736(5) . ?
C1S Cl2 1.741(4) . ?
C1S Cl1 1.747(5) . ?
C1S H1S 1.0000 . ?
C2S Cl7 1.685(5) . ?
C2S Cl9 1.693(8) . ?
C2S Cl6 1.709(5) . ?
C2S Cl4 1.735(6) . ?
C2S Cl8 1.802(5) . ?
C2S Cl5 1.851(5) . ?
C2S H2S 1.0000 . ?
C2S H2SA 1.0000 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C82 H82 Cl5^b 0.95 2.78 3.246(6) 111.3 2_566 yes
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
C21 B1 C11 C16 169.9(2) . . . . ?
C61 B1 C11 C16 -11.1(4) . . . . ?
C21 B1 C11 C12 -14.5(4) . . . . ?
C61 B1 C11 C12 164.4(2) . . . . ?
C22 N1 C12 C13 178.7(2) . . . . ?
C46 N1 C12 C13 -1.5(3) . . . . ?
C22 N1 C12 C11 0.1(3) . . . . ?
C46 N1 C12 C11 179.9(2) . . . . ?
C16 C11 C12 C13 12.2(4) . . . . ?
B1 C11 C12 C13 -163.5(2) . . . . ?
C16 C11 C12 N1 -169.2(2) . . . . ?
B1 C11 C12 N1 15.2(4) . . . . ?
N1 C12 C13 C14 165.4(2) . . . . ?
C11 C12 C13 C14 -15.9(4) . . . . ?
N1 C12 C13 B2 -17.8(3) . . . . ?
C11 C12 C13 B2 160.9(2) . . . . ?
C41 B2 C13 C14 -161.8(2) . . . . ?
C31 B2 C13 C14 17.2(4) . . . . ?
C41 B2 C13 C12 21.6(3) . . . . ?
C31 B2 C13 C12 -159.4(3) . . . . ?
C12 C13 C14 C15 7.8(4) . . . . ?
B2 C13 C14 C15 -168.9(3) . . . . ?
C13 C14 C15 C16 4.4(4) . . . . ?
C14 C15 C16 C11 -8.5(4) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
B1 C11 C16 C15 175.8(3) . . . . ?
C11 B1 C21 C26 -173.9(3) . . . . ?
C61 B1 C21 C26 7.1(4) . . . . ?
C11 B1 C21 C22 -0.4(4) . . . . ?
C61 B1 C21 C22 -179.4(3) . . . . ?
C26 C21 C22 C23 8.3(4) . . . . ?
B1 C21 C22 C23 -165.2(3) . . . . ?
C26 C21 C22 N1 -171.3(3) . . . . ?
B1 C21 C22 N1 15.2(4) . . . . ?
C12 N1 C22 C21 -15.4(4) . . . . ?
C46 N1 C22 C21 164.8(2) . . . . ?
C12 N1 C22 C23 165.0(2) . . . . ?
C46 N1 C22 C23 -14.8(4) . . . . ?
C21 C22 C23 C24 -8.5(4) . . . . ?
N1 C22 C23 C24 171.1(3) . . . . ?
C21 C22 C23 B3 177.8(3) . . . . ?
N1 C22 C23 B3 -2.6(4) . . . . ?
C45 B3 C23 C24 -156.2(3) . . . . ?
C51 B3 C23 C24 18.3(5) . . . . ?
C45 B3 C23 C22 17.2(4) . . . . ?
C51 B3 C23 C22 -168.3(3) . . . . ?
C22 C23 C24 C25 2.7(5) . . . . ?
B3 C23 C24 C25 176.3(3) . . . . ?
C23 C24 C25 C26 3.5(6) . . . . ?
C24 C25 C26 C21 -3.8(6) . . . . ?
C22 C21 C26 C25 -2.1(5) . . . . ?
B1 C21 C26 C25 171.5(3) . . . . ?
C41 B2 C31 C36 -168.9(2) . . . . ?
C13 B2 C31 C36 12.1(4) . . . . ?
C41 B2 C31 C32 8.0(4) . . . . ?
C13 B2 C31 C32 -171.0(3) . . . . ?
C42 N2 C32 C33 174.5(2) . . . . ?
C71 N2 C32 C33 -8.0(4) . . . . ?
C42 N2 C32 C31 -5.5(4) . . . . ?
C71 N2 C32 C31 172.1(2) . . . . ?
C36 C31 C32 N2 177.3(2) . . . . ?
B2 C31 C32 N2 0.1(4) . . . . ?
C36 C31 C32 C33 -2.7(4) . . . . ?
B2 C31 C32 C33 -179.8(2) . . . . ?
N2 C32 C33 C34 -179.8(2) . . . . ?
C31 C32 C33 C34 0.1(4) . . . . ?
C32 C33 C34 C35 1.9(4) . . . . ?
C33 C34 C35 C36 -1.2(4) . . . . ?
C34 C35 C36 C31 -1.6(4) . . . . ?
C32 C31 C36 C35 3.4(4) . . . . ?
B2 C31 C36 C35 -179.7(3) . . . . ?
C31 B2 C41 C46 173.4(2) . . . . ?
C13 B2 C41 C46 -7.5(4) . . . . ?
C31 B2 C41 C42 -11.5(4) . . . . ?
C13 B2 C41 C42 167.6(2) . . . . ?
C32 N2 C42 C43 179.6(2) . . . . ?
C71 N2 C42 C43 2.0(4) . . . . ?
C32 N2 C42 C41 1.9(4) . . . . ?
C71 N2 C42 C41 -175.7(2) . . . . ?
C46 C41 C42 N2 -177.8(2) . . . . ?
B2 C41 C42 N2 6.9(4) . . . . ?
C46 C41 C42 C43 4.6(4) . . . . ?
B2 C41 C42 C43 -170.7(3) . . . . ?
N2 C42 C43 C44 -176.1(3) . . . . ?
C41 C42 C43 C44 1.6(4) . . . . ?
C42 C43 C44 N3 175.1(3) . . . . ?
C42 C43 C44 C45 -6.1(4) . . . . ?
C52 N3 C44 C43 -175.3(3) . . . . ?
C81 N3 C44 C43 4.2(4) . . . . ?
C52 N3 C44 C45 5.8(4) . . . . ?
C81 N3 C44 C45 -174.7(3) . . . . ?
C43 C44 C45 C46 4.3(4) . . . . ?
N3 C44 C45 C46 -176.9(2) . . . . ?
C43 C44 C45 B3 -173.8(3) . . . . ?
N3 C44 C45 B3 5.0(4) . . . . ?
C23 B3 C45 C46 -16.0(4) . . . . ?
C51 B3 C45 C46 168.9(2) . . . . ?
C23 B3 C45 C44 162.0(2) . . . . ?
C51 B3 C45 C44 -13.2(4) . . . . ?
C42 C41 C46 C45 -6.4(4) . . . . ?
B2 C41 C46 C45 168.8(2) . . . . ?
C42 C41 C46 N1 173.9(2) . . . . ?
B2 C41 C46 N1 -10.9(4) . . . . ?
C44 C45 C46 C41 2.2(4) . . . . ?
B3 C45 C46 C41 -179.8(2) . . . . ?
C44 C45 C46 N1 -178.1(2) . . . . ?
B3 C45 C46 N1 -0.1(4) . . . . ?
C12 N1 C46 C41 16.2(3) . . . . ?
C22 N1 C46 C41 -164.0(2) . . . . ?
C12 N1 C46 C45 -163.5(2) . . . . ?
C22 N1 C46 C45 16.3(3) . . . . ?
C45 B3 C51 C56 -168.4(3) . . . . ?
C23 B3 C51 C56 17.3(5) . . . . ?
C45 B3 C51 C52 11.2(4) . . . . ?
C23 B3 C51 C52 -163.1(3) . . . . ?
C44 N3 C52 C53 172.0(3) . . . . ?
C81 N3 C52 C53 -7.5(4) . . . . ?
C44 N3 C52 C51 -7.7(4) . . . . ?
C81 N3 C52 C51 172.8(3) . . . . ?
C56 C51 C52 N3 178.3(3) . . . . ?
B3 C51 C52 N3 -1.3(4) . . . . ?
C56 C51 C52 C53 -1.4(4) . . . . ?
B3 C51 C52 C53 179.0(3) . . . . ?
N3 C52 C53 C54 179.1(3) . . . . ?
C51 C52 C53 C54 -1.2(4) . . . . ?
C52 C53 C54 C55 2.3(5) . . . . ?
C53 C54 C55 C56 -0.7(5) . . . . ?
C54 C55 C56 C51 -2.0(5) . . . . ?
C52 C51 C56 C55 3.0(4) . . . . ?
B3 C51 C56 C55 -177.4(3) . . . . ?
C11 B1 C61 C62 -98.8(3) . . . . ?
C21 B1 C61 C62 80.1(4) . . . . ?
C11 B1 C61 C66 84.3(4) . . . . ?
C21 B1 C61 C66 -96.8(4) . . . . ?
C66 C61 C62 C63 0.3(4) . . . . ?
B1 C61 C62 C63 -176.7(3) . . . . ?
C66 C61 C62 C67 -177.7(3) . . . . ?
B1 C61 C62 C67 5.3(4) . . . . ?
C61 C62 C63 C64 0.3(5) . . . . ?
C67 C62 C63 C64 178.4(3) . . . . ?
C62 C63 C64 C65 -0.8(5) . . . . ?
C62 C63 C64 C68 179.2(3) . . . . ?
C63 C64 C65 C66 0.7(5) . . . . ?
C68 C64 C65 C66 -179.3(4) . . . . ?
C64 C65 C66 C61 -0.1(5) . . . . ?
C64 C65 C66 C69 179.2(3) . . . . ?
C62 C61 C66 C65 -0.5(5) . . . . ?
B1 C61 C66 C65 176.4(3) . . . . ?
C62 C61 C66 C69 -179.7(3) . . . . ?
B1 C61 C66 C69 -2.8(5) . . . . ?
C42 N2 C71 C72 89.0(3) . . . . ?
C32 N2 C71 C72 -88.7(3) . . . . ?
C42 N2 C71 C76 -88.8(3) . . . . ?
C32 N2 C71 C76 93.4(3) . . . . ?
C76 C71 C72 C73 1.7(4) . . . . ?
N2 C71 C72 C73 -176.1(3) . . . . ?
C71 C72 C73 C74 -1.4(5) . . . . ?
C72 C73 C74 C75 0.5(5) . . . . ?
C73 C74 C75 C76 0.0(5) . . . . ?
C72 C71 C76 C75 -1.2(4) . . . . ?
N2 C71 C76 C75 176.7(3) . . . . ?
C74 C75 C76 C71 0.3(5) . . . . ?
C44 N3 C81 C82 -87.6(4) . . . . ?
C52 N3 C81 C82 92.0(4) . . . . ?
C44 N3 C81 C86 91.8(3) . . . . ?
C52 N3 C81 C86 -88.6(4) . . . . ?
C86 C81 C82 C83 0.5(6) . . . . ?
N3 C81 C82 C83 179.9(4) . . . . ?
C81 C82 C83 C84 -0.4(8) . . . . ?
C82 C83 C84 C85 0.3(8) . . . . ?
C83 C84 C85 C86 -0.1(7) . . . . ?
C82 C81 C86 C85 -0.3(5) . . . . ?
N3 C81 C86 C85 -179.7(3) . . . . ?
C84 C85 C86 C81 0.2(5) . . . . ?
