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#$Date: 2024-10-06 10:13:29 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295205 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/23/1572399.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_1572399
loop_
_publ_author_name
'Kovács, Benjámin'
'Földes, Tamás'
'Szabó, Márk'
'Dorkó, Éva'
'Kótai, Bianka'
'Laczkó, Gergely'
'Holczbauer, Tamás'
'Domján, Attila'
'Pápai, Imre'
'Soós, Tibor'
_publ_section_title
;
 Illuminating the multiple Lewis acidity of triaryl-boranes via
 atropisomeric dative adducts.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              15679
_journal_page_last               15689
_journal_paper_doi               10.1039/d4sc00925h
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety
;
C18 H10 B Cl5 F O 1-, C5 H12 N 1+, C5 H11 N
;
_chemical_formula_sum            'C28 H33 B Cl5 F N2 O'
_chemical_formula_weight         620.62
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-05-19 deposited with the CCDC.	2024-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.522(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5595(2)
_cell_length_b                   18.0868(4)
_cell_length_c                   18.9345(4)
_cell_measurement_reflns_used    131696
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.095
_cell_measurement_theta_min      3.02
_cell_volume                     2890.94(13)
_computing_cell_refinement       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_collection       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_reduction        'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       RX
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            116433
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.025
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  0.986656
_exptl_absorpt_correction_T_min  0.958676
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 T.Higashi, Numerical Absorption Correction, NUMABS, 2002
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: piperidine'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5286
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0509
_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)+(0.0444P)²+3.6442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5089
_reflns_number_total             5286
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00925h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1572399--1572400.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1572399
_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   0.776
_shelx_estimated_absorpt_t_max   0.901
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
Cl2 Cl 1.32900(7) 0.25943(4) 0.12875(4) 0.02958(16) Uani 1 1 d . . . . .
Cl3 Cl 1.02192(9) 0.17579(4) -0.09227(3) 0.03600(18) Uani 1 1 d . . . . .
Cl1 Cl 0.72723(8) 0.22157(4) 0.19054(4) 0.03560(18) Uani 1 1 d . . . . .
Cl4 Cl 0.99032(11) 0.39126(4) 0.10963(4) 0.0459(2) Uani 1 1 d . . . . .
Cl5A Cl 0.8315(5) 0.0466(2) 0.0948(3) 0.0452(5) Uani 0.6 1 d . . P A 1
F1A F 0.7172(15) 0.3220(7) 0.0170(5) 0.0433(7) Uani 0.4 1 d . . P A 1
F1B F 0.8547(13) 0.0553(6) 0.0960(8) 0.0452(5) Uani 0.6 1 d . . P B 2
Cl5B Cl 0.6925(6) 0.3143(2) -0.00199(17) 0.0433(7) Uani 0.4 1 d . . P B 2
O1 O 1.0850(2) 0.14879(9) 0.06388(9) 0.0227(4) Uani 1 1 d . . . . .
H1O H 1.066781 0.129120 0.023461 0.058(11) Uiso 1 1 d R . . . .
C1 C 1.0280(3) 0.23279(13) 0.15625(13) 0.0211(5) Uani 1 1 d . . . . .
C2 C 0.9340(3) 0.22865(14) 0.21012(14) 0.0247(5) Uani 1 1 d . . . . .
C3 C 0.9911(3) 0.23220(14) 0.28336(14) 0.0288(6) Uani 1 1 d . . . . .
H3 H 0.920517 0.227569 0.316893 0.040 Uiso 1 1 calc R U . . .
C4 C 1.1511(3) 0.24248(15) 0.30682(14) 0.0306(6) Uani 1 1 d . . . . .
H4 H 1.192206 0.243847 0.356575 0.043 Uiso 1 1 calc R U . . .
C5 C 1.2499(3) 0.25071(14) 0.25707(14) 0.0277(6) Uani 1 1 d . . . . .
H5 H 1.359694 0.259680 0.272092 0.039 Uiso 1 1 calc R U . . .
C6 C 1.1881(3) 0.24582(13) 0.18489(13) 0.0231(5) Uani 1 1 d . . . . .
C7 C 1.0249(3) 0.27992(14) 0.01484(13) 0.0226(5) Uani 1 1 d . . . . .
C8 C 1.0551(3) 0.26513(15) -0.05418(14) 0.0272(6) Uani 1 1 d . . . . .
C9 C 1.1061(3) 0.31573(19) -0.10063(15) 0.0381(7) Uani 1 1 d . . . . .
H9 H 1.124714 0.300844 -0.146635 0.053 Uiso 1 1 calc R U . . .
C10 C 1.1292(3) 0.38820(19) -0.07836(17) 0.0427(8) Uani 1 1 d . . . . .
H10 H 1.167391 0.423700 -0.108344 0.060 Uiso 1 1 calc R U . . .
C11 C 1.0964(4) 0.40848(17) -0.01235(17) 0.0397(7) Uani 1 1 d . . . . .
H11 H 1.109531 0.458348 0.003249 0.056 Uiso 1 1 calc R U . . .
C12 C 1.0442(3) 0.35574(15) 0.03106(15) 0.0304(6) Uani 1 1 d . . . . .
C13A C 0.792(3) 0.1945(10) 0.0408(13) 0.019(2) Uani 0.6 1 d . U P A 1
C14A C 0.7205(17) 0.1246(7) 0.0448(8) 0.024(2) Uani 0.6 1 d . U P A 1
C15A C 0.5619(11) 0.1056(4) 0.0191(5) 0.0272(18) Uani 0.6 1 d . U P A 1
H15A H 0.524325 0.056585 0.023026 0.041 Uiso 0.6 1 calc R U P A 1
C16A C 0.4640(11) 0.1606(5) -0.0117(4) 0.0272(17) Uani 0.6 1 d . U P A 1
H16A H 0.356943 0.149690 -0.031068 0.041 Uiso 0.6 1 calc R U P A 1
C17A C 0.5195(10) 0.2316(4) -0.0150(5) 0.0270(16) Uani 0.6 1 d . U P A 1
H17A H 0.451480 0.270252 -0.035306 0.041 Uiso 0.6 1 calc R U P A 1
C18A C 0.675(3) 0.2450(10) 0.0118(15) 0.035(4) Uani 0.6 1 d . U P A 1
C13B C 0.789(5) 0.1811(17) 0.047(2) 0.019(2) Uani 0.4 1 d . U P B 2
C14B C 0.671(5) 0.2284(15) 0.008(2) 0.026(4) Uani 0.4 1 d . U P B 2
C15B C 0.5112(19) 0.2006(9) -0.0156(8) 0.037(4) Uani 0.4 1 d . U P B 2
H15B H 0.430637 0.232689 -0.038515 0.056 Uiso 0.4 1 calc R U P B 2
C16B C 0.479(2) 0.1285(9) -0.0049(8) 0.039(3) Uani 0.4 1 d . U P B 2
H16B H 0.376273 0.109337 -0.022041 0.058 Uiso 0.4 1 calc R U P B 2
C17B C 0.5961(19) 0.0827(8) 0.0312(8) 0.041(4) Uani 0.4 1 d . U P B 2
H17B H 0.572269 0.032455 0.039359 0.062 Uiso 0.4 1 calc R U P B 2
C18B C 0.746(3) 0.1091(10) 0.0552(12) 0.026(4) Uani 0.4 1 d . U P B 2
B1 B 0.9791(3) 0.21351(15) 0.06933(15) 0.0216(6) Uani 1 1 d . . . . .
N1 N 0.2515(3) 0.05648(13) 0.16157(12) 0.0261(5) Uani 1 1 d . . . . .
C19 C 0.4142(3) 0.08176(15) 0.19143(14) 0.0296(6) Uani 1 1 d . . . . .
H19A H 0.407971 0.123992 0.224109 0.041 Uiso 1 1 calc R U . . .
H19B H 0.467741 0.098982 0.151930 0.041 Uiso 1 1 calc R U . . .
C20 C 0.5105(3) 0.02031(16) 0.23187(15) 0.0345(6) Uani 1 1 d . . . . .
H20A H 0.466044 0.008449 0.275569 0.048 Uiso 1 1 calc R U . . .
H20B H 0.620828 0.037504 0.246946 0.048 Uiso 1 1 calc R U . . .
C21 C 0.5114(3) -0.04942(16) 0.18656(16) 0.0366(7) Uani 1 1 d . . . . .
H21A H 0.570442 -0.039896 0.146738 0.051 Uiso 1 1 calc R U . . .
H21B H 0.565715 -0.089778 0.216325 0.051 Uiso 1 1 calc R U . . .
C22 C 0.3433(3) -0.07287(15) 0.15648(16) 0.0323(6) Uani 1 1 d . . . . .
H22A H 0.346279 -0.115683 0.124145 0.045 Uiso 1 1 calc R U . . .
H22B H 0.288881 -0.088595 0.196212 0.045 Uiso 1 1 calc R U . . .
C23 C 0.2511(3) -0.01056(14) 0.11564(15) 0.0300(6) Uani 1 1 d . . . . .
H23A H 0.298943 0.001683 0.072927 0.042 Uiso 1 1 calc R U . . .
H23B H 0.140596 -0.026661 0.099092 0.042 Uiso 1 1 calc R U . . .
N2 N 0.4230(3) 0.52625(15) 0.22789(13) 0.0359(6) Uani 1 1 d . . . . .
C24 C 0.4955(4) 0.45226(18) 0.22958(16) 0.0417(7) Uani 1 1 d . . . . .
H24A H 0.410645 0.414578 0.225605 0.058 Uiso 1 1 calc R U . . .
H24B H 0.564776 0.445314 0.276426 0.058 Uiso 1 1 calc R U . . .
C25 C 0.5928(4) 0.43938(19) 0.17024(17) 0.0419(7) Uani 1 1 d . . . . .
H25A H 0.687529 0.471616 0.178005 0.059 Uiso 1 1 calc R U . . .
H25B H 0.628996 0.387341 0.171522 0.059 Uiso 1 1 calc R U . . .
C26 C 0.4947(4) 0.4560(2) 0.09760(17) 0.0473(8) Uani 1 1 d . . . . .
H26A H 0.409862 0.418532 0.086599 0.066 Uiso 1 1 calc R U . . .
H26B H 0.562991 0.452790 0.060307 0.066 Uiso 1 1 calc R U . . .
C27 C 0.4210(4) 0.5325(2) 0.09600(17) 0.0478(8) Uani 1 1 d . . . . .
H27A H 0.349286 0.539883 0.049851 0.067 Uiso 1 1 calc R U . . .
H27B H 0.505309 0.570485 0.099898 0.067 Uiso 1 1 calc R U . . .
C28 C 0.3282(4) 0.54161(17) 0.15743(16) 0.0389(7) Uani 1 1 d . . . . .
H28A H 0.287298 0.592839 0.157092 0.054 Uiso 1 1 calc R U . . .
H28B H 0.235966 0.507802 0.149705 0.054 Uiso 1 1 calc R U . . .
H1NA H 0.199(4) 0.0458(18) 0.1971(18) 0.039(9) Uiso 1 1 d . . . . .
H1NB H 0.201(4) 0.0890(19) 0.1359(18) 0.039(9) Uiso 1 1 d . . . . .
H2N H 0.487(4) 0.556(2) 0.2331(18) 0.037(10) Uiso 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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
B1 O1 H1O 111.9 . . ?
C2 C1 C6 111.6(2) . . ?
C2 C1 B1 128.8(2) . . ?
C6 C1 B1 119.0(2) . . ?
C3 C2 C1 124.9(2) . . ?
C3 C2 Cl1 112.9(2) . . ?
C1 C2 Cl1 122.09(19) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 125.4(2) . . ?
C5 C6 Cl2 113.6(2) . . ?
C1 C6 Cl2 120.92(19) . . ?
C8 C7 C12 110.9(2) . . ?
C8 C7 B1 122.5(2) . . ?
C12 C7 B1 126.6(2) . . ?
C9 C8 C7 126.3(3) . . ?
C9 C8 Cl3 112.9(2) . . ?
C7 C8 Cl3 120.8(2) . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 125.5(3) . . ?
C11 C12 Cl4 114.1(2) . . ?
C7 C12 Cl4 120.3(2) . . ?
C18A C13A C14A 108(2) . . ?
C18A C13A B1 126.2(16) . . ?
C14A C13A B1 125.3(16) . . ?
C15A C14A C13A 127.0(14) . . ?
C15A C14A Cl5A 111.8(9) . . ?
C13A C14A Cl5A 121.0(14) . . ?
C16A C15A C14A 117.2(8) . . ?
C16A C15A H15A 121.4 . . ?
C14A C15A H15A 121.4 . . ?
C15A C16A C17A 120.5(8) . . ?
C15A C16A H16A 119.8 . . ?
C17A C16A H16A 119.8 . . ?
C18A C17A C16A 118.2(11) . . ?
C18A C17A H17A 120.9 . . ?
C16A C17A H17A 120.9 . . ?
C17A C18A C13A 128.4(18) . . ?
C17A C18A F1A 114.7(17) . . ?
C13A C18A F1A 117(2) . . ?
C18B C13B C14B 117(3) . . ?
C18B C13B B1 124(3) . . ?
C14B C13B B1 119(2) . . ?
C13B C14B C15B 120(3) . . ?
C13B C14B Cl5B 124(3) . . ?
C15B C14B Cl5B 115(2) . . ?
C16B C15B C14B 119.3(17) . . ?
C16B C15B H15B 120.3 . . ?
C14B C15B H15B 120.3 . . ?
C15B C16B C17B 119.8(14) . . ?
C15B C16B H16B 120.1 . . ?
C17B C16B H16B 120.1 . . ?
C18B C17B C16B 120.9(14) . . ?
C18B C17B H17B 119.5 . . ?
C16B C17B H17B 119.5 . . ?
C13B C18B C17B 123(2) . . ?
C13B C18B F1B 122(2) . . ?
C17B C18B F1B 114.7(15) . . ?
O1 B1 C13A 112.6(8) . . ?
O1 B1 C1 100.12(19) . . ?
C13A B1 C1 116.2(9) . . ?
O1 B1 C7 108.25(19) . . ?
C13A B1 C7 105.3(7) . . ?
C1 B1 C7 114.4(2) . . ?
O1 B1 C13B 106.0(12) . . ?
C1 B1 C13B 113.1(14) . . ?
C7 B1 C13B 113.5(11) . . ?
C19 N1 C23 112.5(2) . . ?
C19 N1 H1NA 110(2) . . ?
C23 N1 H1NA 108(2) . . ?
C19 N1 H1NB 112(2) . . ?
C23 N1 H1NB 106(2) . . ?
H1NA N1 H1NB 108(3) . . ?
N1 C19 C20 111.4(2) . . ?
N1 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
N1 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 112.0(2) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 110.5(2) . . ?
C22 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C23 C22 C21 111.4(2) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
N1 C23 C22 110.9(2) . . ?
N1 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.0 . . ?
C28 N2 C24 111.0(2) . . ?
C28 N2 H2N 105(3) . . ?
C24 N2 H2N 110(3) . . ?
N2 C24 C25 113.8(3) . . ?
N2 C24 H24A 108.8 . . ?
C25 C24 H24A 108.8 . . ?
N2 C24 H24B 108.8 . . ?
C25 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C26 C25 C24 110.5(3) . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 C27 111.4(3) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 C28 110.5(3) . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
N2 C28 C27 113.2(3) . . ?
N2 C28 H28A 108.9 . . ?
C27 C28 H28A 108.9 . . ?
N2 C28 H28B 108.9 . . ?
C27 C28 H28B 108.9 . . ?
H28A C28 H28B 107.8 . . ?
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
Cl2 C6 1.752(3) . ?
Cl3 C8 1.773(3) . ?
Cl1 C2 1.752(3) . ?
Cl4 C12 1.751(3) . ?
Cl5A C14A 1.868(13) . ?
F1A C18A 1.44(2) . ?
F1B C18B 1.47(2) . ?
Cl5B C14B 1.58(3) . ?
O1 B1 1.495(3) . ?
O1 H1O 0.8350 . ?
C1 C2 1.402(4) . ?
C1 C6 1.408(4) . ?
C1 B1 1.667(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.399(4) . ?
C7 C12 1.409(4) . ?
C7 B1 1.672(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.381(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C13A C18A 1.40(3) . ?
C13A C14A 1.41(2) . ?
C13A B1 1.64(3) . ?
C14A C15A 1.407(18) . ?
C15A C16A 1.368(10) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.373(10) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.36(3) . ?
C17A H17A 0.9500 . ?
C13B C18B 1.37(4) . ?
C13B C14B 1.42(5) . ?
C13B B1 1.72(4) . ?
C14B C15B 1.46(4) . ?
C15B C16B 1.354(17) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.391(18) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.37(3) . ?
C17B H17B 0.9500 . ?
N1 C19 1.486(4) . ?
N1 C23 1.492(3) . ?
N1 H1NA 0.89(3) . ?
N1 H1NB 0.84(4) . ?
C19 C20 1.514(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.526(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.517(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.513(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
N2 C28 1.469(4) . ?
N2 C24 1.473(4) . ?
N2 H2N 0.76(4) . ?
C24 C25 1.523(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.518(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.520(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.522(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
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
O1 H1O Cl3 0.83 2.32 2.9569(18) 133 . yes
N1 H1NB O1 0.84(4) 1.89(4) 2.714(3) 169(3) 1_455 yes
N1 H1NA N2 0.89(3) 1.93(4) 2.819(3) 177(3) 2_545 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
C6 C1 C2 C3 -3.8(4) . . . . ?
B1 C1 C2 C3 167.2(2) . . . . ?
C6 C1 C2 Cl1 173.87(18) . . . . ?
B1 C1 C2 Cl1 -15.1(4) . . . . ?
C1 C2 C3 C4 1.8(4) . . . . ?
Cl1 C2 C3 C4 -176.0(2) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 Cl2 178.8(2) . . . . ?
C2 C1 C6 C5 2.9(4) . . . . ?
B1 C1 C6 C5 -169.1(2) . . . . ?
C2 C1 C6 Cl2 -175.80(18) . . . . ?
B1 C1 C6 Cl2 12.2(3) . . . . ?
C12 C7 C8 C9 3.5(4) . . . . ?
B1 C7 C8 C9 -174.5(2) . . . . ?
C12 C7 C8 Cl3 -174.04(18) . . . . ?
B1 C7 C8 Cl3 8.0(3) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
Cl3 C8 C9 C10 177.1(2) . . . . ?
C8 C9 C10 C11 -2.1(4) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C10 C11 C12 C7 2.1(4) . . . . ?
C10 C11 C12 Cl4 -174.5(2) . . . . ?
C8 C7 C12 C11 -4.2(4) . . . . ?
B1 C7 C12 C11 173.6(3) . . . . ?
C8 C7 C12 Cl4 172.12(19) . . . . ?
B1 C7 C12 Cl4 -10.0(4) . . . . ?
C18A C13A C14A C15A 5(3) . . . . ?
B1 C13A C14A C15A -178.0(14) . . . . ?
C18A C13A C14A Cl5A -169.6(17) . . . . ?
B1 C13A C14A Cl5A 8(3) . . . . ?
C13A C14A C15A C16A -2(2) . . . . ?
Cl5A C14A C15A C16A 173.2(8) . . . . ?
C14A C15A C16A C17A -1.9(15) . . . . ?
C15A C16A C17A C18A 1.5(19) . . . . ?
C16A C17A C18A C13A 3(4) . . . . ?
C16A C17A C18A F1A -170.4(14) . . . . ?
C14A C13A C18A C17A -5(4) . . . . ?
B1 C13A C18A C17A 177(2) . . . . ?
C14A C13A C18A F1A 167(2) . . . . ?
B1 C13A C18A F1A -10(4) . . . . ?
C18B C13B C14B C15B 3(5) . . . . ?
B1 C13B C14B C15B 176(3) . . . . ?
C18B C13B C14B Cl5B 175(3) . . . . ?
B1 C13B C14B Cl5B -12(5) . . . . ?
C13B C14B C15B C16B -4(4) . . . . ?
Cl5B C14B C15B C16B -176.0(18) . . . . ?
C14B C15B C16B C17B 2(3) . . . . ?
C15B C16B C17B C18B -1(3) . . . . ?
C14B C13B C18B C17B -2(5) . . . . ?
B1 C13B C18B C17B -174(2) . . . . ?
C14B C13B C18B F1B -177(3) . . . . ?
B1 C13B C18B F1B 10(5) . . . . ?
C16B C17B C18B C13B 1(4) . . . . ?
C16B C17B C18B F1B 176.7(15) . . . . ?
C18A C13A B1 O1 -152(2) . . . . ?
C14A C13A B1 O1 31(2) . . . . ?
C18A C13A B1 C1 93(2) . . . . ?
C14A C13A B1 C1 -84(2) . . . . ?
C18A C13A B1 C7 -35(3) . . . . ?
C14A C13A B1 C7 148.7(19) . . . . ?
C2 C1 B1 O1 -115.1(3) . . . . ?
C6 C1 B1 O1 55.3(3) . . . . ?
C2 C1 B1 C13A 6.3(8) . . . . ?
C6 C1 B1 C13A 176.8(7) . . . . ?
C2 C1 B1 C7 129.4(3) . . . . ?
C6 C1 B1 C7 -60.2(3) . . . . ?
C2 C1 B1 C13B -2.7(13) . . . . ?
C6 C1 B1 C13B 167.7(12) . . . . ?
C8 C7 B1 O1 42.5(3) . . . . ?
C12 C7 B1 O1 -135.1(2) . . . . ?
C8 C7 B1 C13A -78.1(10) . . . . ?
C12 C7 B1 C13A 104.3(10) . . . . ?
C8 C7 B1 C1 153.2(2) . . . . ?
C12 C7 B1 C1 -24.4(3) . . . . ?
C8 C7 B1 C13B -74.9(15) . . . . ?
C12 C7 B1 C13B 107.5(15) . . . . ?
C18B C13B B1 O1 27(4) . . . . ?
C14B C13B B1 O1 -145(3) . . . . ?
C18B C13B B1 C1 -82(3) . . . . ?
C14B C13B B1 C1 106(3) . . . . ?
C18B C13B B1 C7 146(3) . . . . ?
C14B C13B B1 C7 -26(4) . . . . ?
C23 N1 C19 C20 -55.0(3) . . . . ?
N1 C19 C20 C21 53.5(3) . . . . ?
C19 C20 C21 C22 -53.3(3) . . . . ?
C20 C21 C22 C23 54.5(3) . . . . ?
C19 N1 C23 C22 56.3(3) . . . . ?
C21 C22 C23 N1 -55.9(3) . . . . ?
C28 N2 C24 C25 54.3(3) . . . . ?
N2 C24 C25 C26 -53.6(4) . . . . ?
C24 C25 C26 C27 52.7(4) . . . . ?
C25 C26 C27 C28 -53.5(4) . . . . ?
C24 N2 C28 C27 -54.8(3) . . . . ?
C26 C27 C28 N2 55.0(4) . . . . ?
