#------------------------------------------------------------------------------
#$Date: 2022-10-12 05:21:48 +0300 (Wed, 12 Oct 2022) $
#$Revision: 278546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567765.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1567765
loop_
_publ_author_name
'Shimazaki, Runa'
'Sadakiyo, Masaaki'
_publ_section_title
;
 Ethidium tetraphenylborate acetonitrile disolvate
;
_journal_coeditor_code           HB4412
_journal_issue                   10
_journal_name_full               IUCrData
_journal_page_first              x220951
_journal_paper_doi               10.1107/S2414314622009518
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          'C21 H20 N3 +, C24 H20 B -, 2C H3 N'
_chemical_formula_moiety         'C21 H20 N3 +, C24 H20 B -, 2(C H3 N)'
_chemical_formula_sum            'C49 H46 B N5'
_chemical_formula_weight         715.72
_chemical_name_common            (C21H20N3)(C24H20B1)(C2H3N1)2
_chemical_name_systematic
;
3,8-Diamino-5-ethyl-6-phenylphenanthridin-5-ium
tetraphenylborate acetonitrile disolvate
;
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                92.202(4)
_cell_angle_beta                 113.379(3)
_cell_angle_gamma                117.604(4)
_cell_formula_units_Z            2
_cell_length_a                   13.5215(13)
_cell_length_b                   13.5537(14)
_cell_length_c                   13.6079(14)
_cell_measurement_reflns_used    5009
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      2.75
_cell_volume                     1951.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX4 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg 1999)'
_computing_publication_material  'Yadokari-XG (Kabuto 2009)'
_computing_structure_refinement  'SHELXL2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR2019 (Burla 2015)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.761
_diffrn_measurement_device_type  'Bruker PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24904
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         30.953
_diffrn_reflns_theta_min         1.695
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Krause et al., 2015)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         9444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0596
_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)+(0.0555P)²+0.6357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                7510
_reflns_number_total             9444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4412.cif
_cod_data_source_block           I
_cod_original_cell_volume        1951.3(3)
_cod_database_code               1567765
_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   0.979
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.10283(13) 0.18417(12) 0.65451(11) 0.0151(3) Uani d 1 . .
C C2 -0.02177(13) 0.12168(12) 0.64193(12) 0.0158(3) Uani d 1 . .
C C3 -0.05470(14) 0.03582(13) 0.69845(12) 0.0178(3) Uani d 1 . .
H H3 0.007723 0.021889 0.747351 0.021 Uiso calc 1 . .
C C4 -0.17723(14) -0.02804(13) 0.68301(12) 0.0180(3) Uani d 1 . .
C C5 -0.26821(14) -0.00588(14) 0.60872(13) 0.0208(3) Uani d 1 . .
H H5 -0.352926 -0.050353 0.596273 0.025 Uiso calc 1 . .
C C6 -0.23797(14) 0.07748(14) 0.55434(13) 0.0196(3) Uani d 1 . .
H H6 -0.301549 0.090190 0.505573 0.024 Uiso calc 1 . .
C C7 -0.11306(13) 0.14519(13) 0.56974(12) 0.0160(3) Uani d 1 . .
C C8 -0.07585(14) 0.23343(13) 0.51487(12) 0.0166(3) Uani d 1 . .
C C9 -0.16161(15) 0.26139(13) 0.44044(13) 0.0203(3) Uani d 1 . .
H H9 -0.246831 0.221004 0.427140 0.024 Uiso calc 1 . .
C C10 -0.12532(16) 0.34412(14) 0.38777(13) 0.0221(3) Uani d 1 . .
H H10 -0.185547 0.359570 0.337438 0.026 Uiso calc 1 . .
C C11 0.00140(16) 0.40759(14) 0.40713(12) 0.0206(3) Uani d 1 . .
C C12 0.08861(15) 0.38404(13) 0.48036(12) 0.0202(3) Uani d 1 . .
H H12 0.174244 0.427117 0.495054 0.024 Uiso calc 1 . .
C C13 0.05015(14) 0.29626(13) 0.53290(12) 0.0162(3) Uani d 1 . .
C C14 0.26588(14) 0.32666(13) 0.61385(13) 0.0190(3) Uani d 1 . .
H H14 0.323686 0.320748 0.682834 0.023 Uiso calc 1 . .
H H14A 0.296570 0.409724 0.619650 0.023 Uiso calc 1 . .
C C15 0.26718(16) 0.27342(16) 0.51465(14) 0.0250(4) Uani d 1 . .
H H15 0.353304 0.314013 0.523789 0.037 Uiso calc 1 . .
H H15A 0.238071 0.191490 0.509568 0.037 Uiso calc 1 . .
H H15B 0.210987 0.280359 0.446460 0.037 Uiso calc 1 . .
C C16 0.19764(13) 0.15390(13) 0.72163(12) 0.0159(3) Uani d 1 . .
C C17 0.19897(14) 0.06352(14) 0.67151(13) 0.0216(3) Uani d 1 . .
H H17 0.139450 0.021709 0.595916 0.026 Uiso calc 1 . .
C C18 0.28669(15) 0.03388(15) 0.73113(14) 0.0237(3) Uani d 1 . .
H H18 0.287781 -0.027485 0.696375 0.028 Uiso calc 1 . .
C C19 0.37266(14) 0.09448(14) 0.84176(13) 0.0207(3) Uani d 1 . .
H H19 0.433250 0.074912 0.882714 0.025 Uiso calc 1 . .
C C20 0.37059(14) 0.18335(13) 0.89275(13) 0.0198(3) Uani d 1 . .
H H20 0.429525 0.224226 0.968650 0.024 Uiso calc 1 . .
C C21 0.28259(14) 0.21321(13) 0.83343(12) 0.0182(3) Uani d 1 . .
H H21 0.280468 0.273462 0.868848 0.022 Uiso calc 1 . .
C C22 0.12205(13) 0.29457(13) 0.13371(12) 0.0165(3) Uani d 1 . .
C C23 0.05756(14) 0.18979(13) 0.05175(12) 0.0186(3) Uani d 1 . .
H H23 0.087510 0.186105 0.000094 0.022 Uiso calc 1 . .
C C24 -0.04892(14) 0.09093(13) 0.04352(13) 0.0211(3) Uani d 1 . .
H H24 -0.090456 0.021982 -0.013482 0.025 Uiso calc 1 . .
C C25 -0.09401(14) 0.09344(14) 0.11858(13) 0.0218(3) Uani d 1 . .
H H25 -0.167324 0.026941 0.112436 0.026 Uiso calc 1 . .
C C26 -0.03077(14) 0.19422(14) 0.20276(13) 0.0203(3) Uani d 1 . .
H H26 -0.059578 0.196448 0.255658 0.024 Uiso calc 1 . .
C C27 0.07526(14) 0.29226(13) 0.20949(12) 0.0182(3) Uani d 1 . .
H H27 0.117457 0.360257 0.267857 0.022 Uiso calc 1 . .
C C28 0.27575(14) 0.53038(13) 0.20596(12) 0.0165(3) Uani d 1 . .
C C29 0.39743(14) 0.62668(13) 0.27226(13) 0.0214(3) Uani d 1 . .
H H29 0.467612 0.618068 0.288191 0.026 Uiso calc 1 . .
C C30 0.42072(17) 0.73433(14) 0.31598(14) 0.0277(4) Uani d 1 . .
H H30 0.505085 0.796966 0.360163 0.033 Uiso calc 1 . .
C C31 0.32062(18) 0.74988(15) 0.29491(15) 0.0285(4) Uani d 1 . .
H H31 0.335320 0.822368 0.325800 0.034 Uiso calc 1 . .
C C32 0.19867(17) 0.65776(15) 0.22795(15) 0.0277(4) Uani d 1 . .
H H32 0.129170 0.667520 0.211816 0.033 Uiso calc 1 . .
C C33 0.17714(14) 0.55105(14) 0.18411(14) 0.0212(3) Uani d 1 . .
H H33 0.092598 0.489771 0.137643 0.025 Uiso calc 1 . .
C C34 0.24620(13) 0.42353(12) 0.02563(12) 0.0156(3) Uani d 1 . .
C C35 0.13375(14) 0.37692(13) -0.07495(12) 0.0182(3) Uani d 1 . .
H H35 0.055675 0.327850 -0.075250 0.022 Uiso calc 1 . .
C C36 0.13246(15) 0.39999(13) -0.17433(13) 0.0201(3) Uani d 1 . .
H H36 0.054400 0.365836 -0.240688 0.024 Uiso calc 1 . .
C C37 0.24450(15) 0.47252(13) -0.17690(13) 0.0203(3) Uani d 1 . .
H H37 0.243851 0.489055 -0.244295 0.024 Uiso calc 1 . .
C C38 0.35770(15) 0.52053(13) -0.07894(13) 0.0201(3) Uani d 1 . .
H H38 0.435400 0.570005 -0.079103 0.024 Uiso calc 1 . .
C C39 0.35716(14) 0.49611(13) 0.01924(12) 0.0179(3) Uani d 1 . .
H H39 0.435672 0.530204 0.085129 0.021 Uiso calc 1 . .
C C40 0.36523(13) 0.38498(12) 0.22126(12) 0.0154(3) Uani d 1 . .
C C41 0.40842(14) 0.33088(13) 0.17341(12) 0.0182(3) Uani d 1 . .
H H41 0.374276 0.310812 0.094729 0.022 Uiso calc 1 . .
C C42 0.49936(15) 0.30514(14) 0.23617(13) 0.0210(3) Uani d 1 . .
H H42 0.526983 0.269754 0.200185 0.025 Uiso calc 1 . .
C C43 0.54946(14) 0.33132(14) 0.35131(13) 0.0216(3) Uani d 1 . .
H H43 0.611657 0.314478 0.394730 0.026 Uiso calc 1 . .
C C44 0.50703(14) 0.38249(13) 0.40172(13) 0.0200(3) Uani d 1 . .
H H44 0.539046 0.399432 0.480192 0.024 Uiso calc 1 . .
C C45 0.41752(14) 0.40920(13) 0.33769(12) 0.0176(3) Uani d 1 . .
H H45 0.390885 0.445202 0.374305 0.021 Uiso calc 1 . .
C C46 0.35854(19) -0.00009(19) 0.12689(16) 0.0409(5) Uani d 1 . .
H H46 0.288511 -0.079545 0.107370 0.061 Uiso calc 1 . .
H H46A 0.397972 0.004480 0.079028 0.061 Uiso calc 1 . .
H H46B 0.326431 0.052423 0.116267 0.061 Uiso calc 1 . .
C C47 0.45173(15) 0.03317(15) 0.24280(15) 0.0261(4) Uani d 1 . .
C C48 0.23117(19) 0.69337(16) -0.02061(17) 0.0344(4) Uani d 1 . .
H H48 0.284178 0.715801 0.060117 0.052 Uiso calc 1 . .
H H48A 0.198998 0.611852 -0.051468 0.052 Uiso calc 1 . .
H H48B 0.160080 0.704240 -0.036650 0.052 Uiso calc 1 . .
C C49 0.30580(16) 0.76501(15) -0.07085(14) 0.0267(4) Uani d 1 . .
N N1 0.13589(11) 0.26686(11) 0.60274(10) 0.0160(3) Uani d 1 . .
N N2 -0.21233(13) -0.10941(12) 0.73872(12) 0.0244(3) Uani d 1 . .
H H2 -0.156112 -0.122643 0.786359 0.029 Uiso calc 1 . .
H H2A -0.291077 -0.148392 0.726836 0.029 Uiso calc 1 . .
N N3 0.03525(15) 0.49152(13) 0.35363(12) 0.0277(3) Uani d 1 . .
H H3A 0.113866 0.531937 0.365386 0.033 Uiso calc 1 . .
H H3B -0.021640 0.504984 0.307539 0.033 Uiso calc 1 . .
B B1 0.25161(15) 0.40776(14) 0.14659(13) 0.0148(3) Uani d 1 . .
N N4 0.52247(15) 0.05982(14) 0.33369(14) 0.0347(4) Uani d 1 . .
N N5 0.36569(16) 0.82227(15) -0.10868(14) 0.0370(4) Uani d 1 . .
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'
N N 0.0061 0.0033 '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
N1 C1 C2 . . 121.19(13) ?
N1 C1 C16 . . 118.78(12) ?
C2 C1 C16 . . 119.96(13) ?
C3 C2 C7 . . 120.71(13) ?
C3 C2 C1 . . 120.51(13) ?
C7 C2 C1 . . 118.76(14) ?
C4 C3 C2 . . 120.53(14) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
N2 C4 C3 . . 122.46(14) ?
N2 C4 C5 . . 119.23(13) ?
C3 C4 C5 . . 118.29(14) ?
C6 C5 C4 . . 122.05(14) ?
C6 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
C5 C6 C7 . . 120.87(14) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C6 C7 C2 . . 117.53(14) ?
C6 C7 C8 . . 123.39(14) ?
C2 C7 C8 . . 119.07(13) ?
C13 C8 C9 . . 117.15(14) ?
C13 C8 C7 . . 120.24(13) ?
C9 C8 C7 . . 122.61(14) ?
C10 C9 C8 . . 121.91(15) ?
C10 C9 H9 . . 119.0 ?
C8 C9 H9 . . 119.0 ?
C9 C10 C11 . . 120.63(15) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
N3 C11 C12 . . 121.56(15) ?
N3 C11 C10 . . 119.15(15) ?
C12 C11 C10 . . 119.29(15) ?
C11 C12 C13 . . 120.01(14) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C12 C13 N1 . . 120.74(13) ?
C12 C13 C8 . . 120.97(14) ?
N1 C13 C8 . . 118.27(13) ?
N1 C14 C15 . . 110.96(12) ?
N1 C14 H14 . . 109.4 ?
C15 C14 H14 . . 109.4 ?
N1 C14 H14A . . 109.4 ?
C15 C14 H14A . . 109.4 ?
H14 C14 H14A . . 108.0 ?
C14 C15 H15 . . 109.5 ?
C14 C15 H15A . . 109.5 ?
H15 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C17 C16 C21 . . 119.83(14) ?
C17 C16 C1 . . 118.98(13) ?
C21 C16 C1 . . 121.18(13) ?
C18 C17 C16 . . 120.48(14) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C19 C18 C17 . . 119.55(15) ?
C19 C18 H18 . . 120.2 ?
C17 C18 H18 . . 120.2 ?
C20 C19 C18 . . 120.29(14) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C21 . . 120.39(14) ?
C19 C20 H20 . . 119.8 ?
C21 C20 H20 . . 119.8 ?
C20 C21 C16 . . 119.43(14) ?
C20 C21 H21 . . 120.3 ?
C16 C21 H21 . . 120.3 ?
C27 C22 C23 . . 115.56(14) ?
C27 C22 B1 . . 122.38(13) ?
C23 C22 B1 . . 121.80(13) ?
C24 C23 C22 . . 122.44(14) ?
C24 C23 H23 . . 118.8 ?
C22 C23 H23 . . 118.8 ?
C25 C24 C23 . . 120.04(14) ?
C25 C24 H24 . . 120.0 ?
C23 C24 H24 . . 120.0 ?
C24 C25 C26 . . 119.28(14) ?
C24 C25 H25 . . 120.4 ?
C26 C25 H25 . . 120.4 ?
C25 C26 C27 . . 119.86(15) ?
C25 C26 H26 . . 120.1 ?
C27 C26 H26 . . 120.1 ?
C26 C27 C22 . . 122.77(14) ?
C26 C27 H27 . . 118.6 ?
C22 C27 H27 . . 118.6 ?
C29 C28 C33 . . 114.76(14) ?
C29 C28 B1 . . 122.18(13) ?
C33 C28 B1 . . 122.68(13) ?
C30 C29 C28 . . 123.39(15) ?
C30 C29 H29 . . 118.3 ?
C28 C29 H29 . . 118.3 ?
C31 C30 C29 . . 119.88(16) ?
C31 C30 H30 . . 120.1 ?
C29 C30 H30 . . 120.1 ?
C30 C31 C32 . . 118.79(16) ?
C30 C31 H31 . . 120.6 ?
C32 C31 H31 . . 120.6 ?
C31 C32 C33 . . 120.57(15) ?
C31 C32 H32 . . 119.7 ?
C33 C32 H32 . . 119.7 ?
C32 C33 C28 . . 122.58(15) ?
C32 C33 H33 . . 118.7 ?
C28 C33 H33 . . 118.7 ?
C39 C34 C35 . . 115.19(14) ?
C39 C34 B1 . . 120.42(12) ?
C35 C34 B1 . . 124.11(13) ?
C36 C35 C34 . . 122.49(14) ?
C36 C35 H35 . . 118.8 ?
C34 C35 H35 . . 118.8 ?
C37 C36 C35 . . 120.44(14) ?
C37 C36 H36 . . 119.8 ?
C35 C36 H36 . . 119.8 ?
C36 C37 C38 . . 118.73(14) ?
C36 C37 H37 . . 120.6 ?
C38 C37 H37 . . 120.6 ?
C39 C38 C37 . . 120.01(14) ?
C39 C38 H38 . . 120.0 ?
C37 C38 H38 . . 120.0 ?
C38 C39 C34 . . 123.13(14) ?
C38 C39 H39 . . 118.4 ?
C34 C39 H39 . . 118.4 ?
C41 C40 C45 . . 115.24(13) ?
C41 C40 B1 . . 122.78(13) ?
C45 C40 B1 . . 121.73(13) ?
C42 C41 C40 . . 122.97(14) ?
C42 C41 H41 . . 118.5 ?
C40 C41 H41 . . 118.5 ?
C43 C42 C41 . . 119.98(14) ?
C43 C42 H42 . . 120.0 ?
C41 C42 H42 . . 120.0 ?
C44 C43 C42 . . 118.84(14) ?
C44 C43 H43 . . 120.6 ?
C42 C43 H43 . . 120.6 ?
C43 C44 C45 . . 120.31(14) ?
C43 C44 H44 . . 119.8 ?
C45 C44 H44 . . 119.8 ?
C44 C45 C40 . . 122.63(14) ?
C44 C45 H45 . . 118.7 ?
C40 C45 H45 . . 118.7 ?
C47 C46 H46 . . 109.5 ?
C47 C46 H46A . . 109.5 ?
H46 C46 H46A . . 109.5 ?
C47 C46 H46B . . 109.5 ?
H46 C46 H46B . . 109.5 ?
H46A C46 H46B . . 109.5 ?
N4 C47 C46 . . 178.3(2) ?
C49 C48 H48 . . 109.5 ?
C49 C48 H48A . . 109.5 ?
H48 C48 H48A . . 109.5 ?
C49 C48 H48B . . 109.5 ?
H48 C48 H48B . . 109.5 ?
H48A C48 H48B . . 109.5 ?
N5 C49 C48 . . 179.0(2) ?
C1 N1 C13 . . 122.40(12) ?
C1 N1 C14 . . 119.54(12) ?
C13 N1 C14 . . 117.99(12) ?
C4 N2 H2 . . 120.0 ?
C4 N2 H2A . . 120.0 ?
H2 N2 H2A . . 120.0 ?
C11 N3 H3A . . 120.0 ?
C11 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C22 B1 C28 . . 112.62(12) ?
C22 B1 C34 . . 112.51(12) ?
C28 B1 C34 . . 103.66(12) ?
C22 B1 C40 . . 104.63(12) ?
C28 B1 C40 . . 111.81(12) ?
C34 B1 C40 . . 111.84(12) ?
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 N1 . 1.3411(19) ?
C1 C2 . 1.422(2) ?
C1 C16 . 1.494(2) ?
C2 C3 . 1.416(2) ?
C2 C7 . 1.420(2) ?
C3 C4 . 1.385(2) ?
C3 H3 . 0.9500 ?
C4 N2 . 1.372(2) ?
C4 C5 . 1.416(2) ?
C5 C6 . 1.367(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.417(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.432(2) ?
C8 C13 . 1.413(2) ?
C8 C9 . 1.421(2) ?
C9 C10 . 1.357(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.416(2) ?
C10 H10 . 0.9500 ?
C11 N3 . 1.371(2) ?
C11 C12 . 1.388(2) ?
C12 C13 . 1.409(2) ?
C12 H12 . 0.9500 ?
C13 N1 . 1.4103(19) ?
C14 N1 . 1.4929(19) ?
C14 C15 . 1.516(2) ?
C14 H14 . 0.9900 ?
C14 H14A . 0.9900 ?
C15 H15 . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C16 C17 . 1.390(2) ?
C16 C21 . 1.394(2) ?
C17 C18 . 1.389(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.387(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.384(2) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.393(2) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
C22 C27 . 1.402(2) ?
C22 C23 . 1.407(2) ?
C22 B1 . 1.643(2) ?
C23 C24 . 1.398(2) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.388(2) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.389(2) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.397(2) ?
C26 H26 . 0.9500 ?
C27 H27 . 0.9500 ?
C28 C29 . 1.402(2) ?
C28 C33 . 1.408(2) ?
C28 B1 . 1.645(2) ?
C29 C30 . 1.393(2) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.385(3) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.386(3) ?
C31 H31 . 0.9500 ?
C32 C33 . 1.392(2) ?
C32 H32 . 0.9500 ?
C33 H33 . 0.9500 ?
C34 C39 . 1.403(2) ?
C34 C35 . 1.406(2) ?
C34 B1 . 1.645(2) ?
C35 C36 . 1.395(2) ?
C35 H35 . 0.9500 ?
C36 C37 . 1.388(2) ?
C36 H36 . 0.9500 ?
C37 C38 . 1.391(2) ?
C37 H37 . 0.9500 ?
C38 C39 . 1.391(2) ?
C38 H38 . 0.9500 ?
C39 H39 . 0.9500 ?
C40 C41 . 1.402(2) ?
C40 C45 . 1.405(2) ?
C40 B1 . 1.647(2) ?
C41 C42 . 1.397(2) ?
C41 H41 . 0.9500 ?
C42 C43 . 1.390(2) ?
C42 H42 . 0.9500 ?
C43 C44 . 1.388(2) ?
C43 H43 . 0.9500 ?
C44 C45 . 1.396(2) ?
C44 H44 . 0.9500 ?
C45 H45 . 0.9500 ?
C46 C47 . 1.456(3) ?
C46 H46 . 0.9800 ?
C46 H46A . 0.9800 ?
C46 H46B . 0.9800 ?
C47 N4 . 1.132(2) ?
C48 C49 . 1.456(3) ?
C48 H48 . 0.9800 ?
C48 H48A . 0.9800 ?
C48 H48B . 0.9800 ?
C49 N5 . 1.141(2) ?
N2 H2 . 0.8800 ?
N2 H2A . 0.8800 ?
N3 H3A . 0.8800 ?
N3 H3B . 0.8800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2 Cg1 2_556 0.88 2.45 3.303(2) 165
N2 H2A Cg4 2_556 0.88 2.62 3.3297(18) 139
C21 H21 Cg3 1_556 0.95 2.75 3.685(2) 167
C25 H25 Cg8 2_556 0.95 2.79 3.632(2) 148
C36 H36 Cg5 1_554 0.95 2.81 3.3593(18) 118
C48 H48 Cg2 1_555 0.98 2.78 3.609(2) 143
C48 H48A Cg3 1_555 0.99 2.61 3.488(2) 149
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -179.05(13) ?
C16 C1 C2 C3 . . . . 4.1(2) ?
N1 C1 C2 C7 . . . . 2.4(2) ?
C16 C1 C2 C7 . . . . -174.45(13) ?
C7 C2 C3 C4 . . . . 1.0(2) ?
C1 C2 C3 C4 . . . . -177.60(13) ?
C2 C3 C4 N2 . . . . -177.87(14) ?
C2 C3 C4 C5 . . . . 0.6(2) ?
N2 C4 C5 C6 . . . . 177.17(14) ?
C3 C4 C5 C6 . . . . -1.4(2) ?
C4 C5 C6 C7 . . . . 0.5(2) ?
C5 C6 C7 C2 . . . . 1.1(2) ?
C5 C6 C7 C8 . . . . 179.81(14) ?
C3 C2 C7 C6 . . . . -1.8(2) ?
C1 C2 C7 C6 . . . . 176.79(13) ?
C3 C2 C7 C8 . . . . 179.41(13) ?
C1 C2 C7 C8 . . . . -2.0(2) ?
C6 C7 C8 C13 . . . . -178.95(13) ?
C2 C7 C8 C13 . . . . -0.2(2) ?
C6 C7 C8 C9 . . . . 0.5(2) ?
C2 C7 C8 C9 . . . . 179.27(13) ?
C13 C8 C9 C10 . . . . 0.5(2) ?
C7 C8 C9 C10 . . . . -179.00(14) ?
C8 C9 C10 C11 . . . . -1.2(2) ?
C9 C10 C11 N3 . . . . -179.20(14) ?
C9 C10 C11 C12 . . . . 0.3(2) ?
N3 C11 C12 C13 . . . . -179.28(14) ?
C10 C11 C12 C13 . . . . 1.2(2) ?
C11 C12 C13 N1 . . . . 176.47(13) ?
C11 C12 C13 C8 . . . . -1.9(2) ?
C9 C8 C13 C12 . . . . 1.0(2) ?
C7 C8 C13 C12 . . . . -179.44(13) ?
C9 C8 C13 N1 . . . . -177.37(13) ?
C7 C8 C13 N1 . . . . 2.2(2) ?
N1 C1 C16 C17 . . . . -93.33(17) ?
C2 C1 C16 C17 . . . . 83.56(18) ?
N1 C1 C16 C21 . . . . 87.83(18) ?
C2 C1 C16 C21 . . . . -95.29(17) ?
C21 C16 C17 C18 . . . . -1.8(2) ?
C1 C16 C17 C18 . . . . 179.33(14) ?
C16 C17 C18 C19 . . . . 0.6(3) ?
C17 C18 C19 C20 . . . . 0.5(2) ?
C18 C19 C20 C21 . . . . -0.3(2) ?
C19 C20 C21 C16 . . . . -0.9(2) ?
C17 C16 C21 C20 . . . . 2.0(2) ?
C1 C16 C21 C20 . . . . -179.19(14) ?
C27 C22 C23 C24 . . . . 2.3(2) ?
B1 C22 C23 C24 . . . . 176.53(14) ?
C22 C23 C24 C25 . . . . -0.7(2) ?
C23 C24 C25 C26 . . . . -1.3(2) ?
C24 C25 C26 C27 . . . . 1.4(2) ?
C25 C26 C27 C22 . . . . 0.3(2) ?
C23 C22 C27 C26 . . . . -2.1(2) ?
B1 C22 C27 C26 . . . . -176.30(14) ?
C33 C28 C29 C30 . . . . 1.4(2) ?
B1 C28 C29 C30 . . . . 174.54(15) ?
C28 C29 C30 C31 . . . . 0.3(3) ?
C29 C30 C31 C32 . . . . -1.6(3) ?
C30 C31 C32 C33 . . . . 1.0(3) ?
C31 C32 C33 C28 . . . . 0.9(3) ?
C29 C28 C33 C32 . . . . -2.0(2) ?
B1 C28 C33 C32 . . . . -175.08(15) ?
C39 C34 C35 C36 . . . . 0.7(2) ?
B1 C34 C35 C36 . . . . 174.57(14) ?
C34 C35 C36 C37 . . . . -0.9(2) ?
C35 C36 C37 C38 . . . . 0.7(2) ?
C36 C37 C38 C39 . . . . -0.4(2) ?
C37 C38 C39 C34 . . . . 0.3(2) ?
C35 C34 C39 C38 . . . . -0.4(2) ?
B1 C34 C39 C38 . . . . -174.51(14) ?
C45 C40 C41 C42 . . . . -1.6(2) ?
B1 C40 C41 C42 . . . . -176.04(14) ?
C40 C41 C42 C43 . . . . 1.2(2) ?
C41 C42 C43 C44 . . . . 0.3(2) ?
C42 C43 C44 C45 . . . . -1.3(2) ?
C43 C44 C45 C40 . . . . 0.9(2) ?
C41 C40 C45 C44 . . . . 0.6(2) ?
B1 C40 C45 C44 . . . . 175.05(13) ?
C2 C1 N1 C13 . . . . -0.4(2) ?
C16 C1 N1 C13 . . . . 176.45(12) ?
C2 C1 N1 C14 . . . . -177.17(12) ?
C16 C1 N1 C14 . . . . -0.33(19) ?
C12 C13 N1 C1 . . . . 179.70(13) ?
C8 C13 N1 C1 . . . . -1.9(2) ?
C12 C13 N1 C14 . . . . -3.5(2) ?
C8 C13 N1 C14 . . . . 174.94(12) ?
C15 C14 N1 C1 . . . . 97.48(16) ?
C15 C14 N1 C13 . . . . -79.45(16) ?
C27 C22 B1 C28 . . . . -30.72(19) ?
C23 C22 B1 C28 . . . . 155.40(13) ?
C27 C22 B1 C34 . . . . -147.44(14) ?
C23 C22 B1 C34 . . . . 38.68(19) ?
C27 C22 B1 C40 . . . . 90.93(16) ?
C23 C22 B1 C40 . . . . -82.95(16) ?
C29 C28 B1 C22 . . . . 148.75(14) ?
C33 C28 B1 C22 . . . . -38.68(19) ?
C29 C28 B1 C34 . . . . -89.37(16) ?
C33 C28 B1 C34 . . . . 83.20(16) ?
C29 C28 B1 C40 . . . . 31.28(19) ?
C33 C28 B1 C40 . . . . -156.15(14) ?
C39 C34 B1 C22 . . . . -164.01(13) ?
C35 C34 B1 C22 . . . . 22.4(2) ?
C39 C34 B1 C28 . . . . 74.04(16) ?
C35 C34 B1 C28 . . . . -99.51(16) ?
C39 C34 B1 C40 . . . . -46.58(18) ?
C35 C34 B1 C40 . . . . 139.86(14) ?
C41 C40 B1 C22 . . . . 93.19(16) ?
C45 C40 B1 C22 . . . . -80.86(16) ?
C41 C40 B1 C28 . . . . -144.63(14) ?
C45 C40 B1 C28 . . . . 41.32(18) ?
C41 C40 B1 C34 . . . . -28.87(19) ?
C45 C40 B1 C34 . . . . 157.08(13) ?
