#------------------------------------------------------------------------------
#$Date: 2023-12-07 13:48:57 +0200 (Thu, 07 Dec 2023) $
#$Revision: 288132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/29/2022932.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_2022932
loop_
_publ_author_name
'Streeter, Cole'
'Wheeler, Kraig A.'
'Lamm, Ashley N.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 tri-aza-triborinotris[1,3,2]benzodi-aza-borole acetone disolvate.
;
_journal_coeditor_code           EX2077
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1104
_journal_page_last               1108
_journal_paper_doi               10.1107/S2056989023009337
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C18 H15 B3 N6, 2C3 H6 O'
_chemical_formula_moiety         'C18 H15 B3 N6, 2(C3 H6 O)'
_chemical_formula_sum            'C24 H27 B3 N6 O2'
_chemical_formula_weight         463.94
_chemical_name_common
2,9,11,18,20,27-Hexaaza-1,10,19-triboraheptacyclo[18.7.0.0^2,10^.0^3,8^.0^11,19^.0^12,17^.0^21,26^]heptacosa-3(8),4,6,12(17),13,15,21(26),22,24-nonaene
_chemical_name_systematic
;
Triazatriborinotris[1,3,2]benzodiazaborole acetone 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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                97.595(3)
_cell_angle_beta                 96.957(3)
_cell_angle_gamma                99.771(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8357(4)
_cell_length_b                   13.6362(9)
_cell_length_c                   15.4653(10)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.325
_cell_measurement_theta_min      3.329
_cell_volume                     1189.13(14)
_computing_cell_refinement
;
SAINT-Plus V8.40B (Bruker, 2020)
;
_computing_data_collection
;
APEX4 Ver. 8.38A (Bruker, 2022)
;
_computing_data_reduction
;
SAINT-Plus Ve8.40B (Bruker, 2020)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL209/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            47276
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.636
_diffrn_reflns_theta_min         2.914
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.55000000000000E-1
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.129
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     369
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0386
_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)+(0.0377P)²+0.3978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                4226
_reflns_number_total             4853
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ex2077sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022932.cif.'
_cod_database_code               2022932
_cod_database_fobs_code          2022932
_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   0.773
_shelx_estimated_absorpt_t_max   0.919
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
O O1 1.06089(19) 0.80696(9) 0.44502(7) 0.0509(3) Uani d 1 . .
C C19 1.4443(2) 0.84484(11) 0.52511(9) 0.0394(3) Uani d 1 . .
H H19A 1.465884 0.900588 0.491055 0.059 Uiso calc 1 . .
H H19B 1.566486 0.804633 0.517058 0.059 Uiso calc 1 . .
H H19C 1.455742 0.871885 0.587746 0.059 Uiso calc 1 . .
C C20 1.2081(2) 0.78000(10) 0.49384(8) 0.0292(3) Uani d 1 . .
C C21 1.1621(3) 0.68044(11) 0.52471(10) 0.0414(3) Uani d 1 . .
H H21A 0.992312 0.654847 0.516480 0.062 Uiso calc 1 . .
H H21B 1.225795 0.688200 0.587362 0.062 Uiso calc 1 . .
H H21C 1.238069 0.632812 0.490587 0.062 Uiso calc 1 . .
O O2 -0.42413(17) 0.45535(8) 0.15098(7) 0.0438(3) Uani d 1 . .
C C22 -0.7168(3) 0.31164(10) 0.15045(10) 0.0444(4) Uani d 1 . .
H H22A -0.746614 0.260253 0.097682 0.067 Uiso calc 1 . .
H H22B -0.863479 0.314031 0.174805 0.067 Uiso calc 1 . .
H H22C -0.600541 0.294781 0.194562 0.067 Uiso calc 1 . .
C C23 -0.6251(2) 0.41159(9) 0.12665(8) 0.0307(3) Uani d 1 . .
C C24 -0.7921(3) 0.45521(12) 0.06874(11) 0.0502(4) Uani d 1 . .
H H24A -0.911786 0.476703 0.102329 0.075 Uiso calc 1 . .
H H24B -0.868343 0.404166 0.018179 0.075 Uiso calc 1 . .
H H24C -0.705855 0.513364 0.047717 0.075 Uiso calc 1 . .
N N1 0.05231(18) 0.94365(8) 0.12177(7) 0.0213(2) Uani d 0.8922(14) A 1
H H1 0.087(3) 1.0065(10) 0.1141(10) 0.026 Uiso d 0.8922(14) A 1
N N2 0.0215(2) 0.79057(11) 0.17389(8) 0.0199(3) Uani d 0.8922(14) A 1
N N3 -0.01420(19) 0.61709(8) 0.23107(7) 0.0223(2) Uani d 0.8922(14) A 1
H H3 -0.155(2) 0.5811(11) 0.2091(10) 0.027 Uiso d 0.8922(14) A 1
N N4 0.3305(3) 0.73686(10) 0.27224(7) 0.0199(3) Uani d 0.8922(14) A 1
N N5 0.70842(18) 0.87612(8) 0.32562(7) 0.0217(2) Uani d 0.8922(14) A 1
H H5 0.808(2) 0.8516(11) 0.3595(9) 0.026 Uiso d 0.8922(14) A 1
N N6 0.3973(2) 0.90929(9) 0.23233(8) 0.0194(2) Uani d 0.8922(14) A 1
C C1 -0.1652(3) 0.88371(13) 0.08577(11) 0.0198(3) Uani d 0.8922(14) A 1
C C2 -0.3450(4) 0.90431(14) 0.02761(13) 0.0224(4) Uani d 0.8922(14) A 1
H H2 -0.329678 0.966365 0.005266 0.027 Uiso calc 0.8922(14) A 1
C C3 -0.5501(3) 0.83056(16) 0.00289(13) 0.0229(4) Uani d 0.8922(14) A 1
H H3A -0.676721 0.843184 -0.036131 0.027 Uiso calc 0.8922(14) A 1
C C4 -0.5705(3) 0.73916(13) 0.03476(11) 0.0229(4) Uani d 0.8922(14) A 1
H H4 -0.710825 0.690246 0.017142 0.027 Uiso calc 0.8922(14) A 1
C C5 -0.3876(3) 0.71828(12) 0.09227(10) 0.0212(3) Uani d 0.8922(14) A 1
H H5A -0.401702 0.655786 0.113858 0.025 Uiso calc 0.8922(14) A 1
C C6 -0.1858(3) 0.79089(14) 0.11696(8) 0.0191(3) Uani d 0.8922(14) A 1
C C7 0.1469(3) 0.57793(15) 0.28473(8) 0.0208(3) Uani d 0.8922(14) A 1
C C8 0.1229(3) 0.48537(15) 0.31331(13) 0.0244(4) Uani d 0.8922(14) A 1
H H8 -0.020650 0.438014 0.298263 0.029 Uiso calc 0.8922(14) A 1
C C9 0.3158(4) 0.46330(17) 0.36499(18) 0.0260(5) Uani d 0.8922(14) A 1
H H9 0.303614 0.400122 0.385324 0.031 Uiso calc 0.8922(14) A 1
C C10 0.5261(3) 0.53338(15) 0.38692(12) 0.0251(4) Uani d 0.8922(14) A 1
H H10 0.656080 0.516669 0.421237 0.030 Uiso calc 0.8922(14) A 1
C C11 0.5489(3) 0.62773(11) 0.35930(10) 0.0227(3) Uani d 0.8922(14) A 1
H H11 0.691815 0.675431 0.374747 0.027 Uiso calc 0.8922(14) A 1
C C12 0.3572(3) 0.64948(10) 0.30890(10) 0.0199(3) Uani d 0.8922(14) A 1
C C13 0.7668(4) 0.97371(11) 0.30686(11) 0.0215(3) Uani d 0.8922(14) A 1
C C14 0.9721(4) 1.04497(16) 0.33531(14) 0.0244(4) Uani d 0.8922(14) A 1
H H14 1.097907 1.031074 0.373927 0.029 Uiso calc 0.8922(14) A 1
C C15 0.9867(4) 1.13764(18) 0.30511(17) 0.0262(5) Uani d 0.8922(14) A 1
H H15 1.125364 1.187461 0.322980 0.031 Uiso calc 0.8922(14) A 1
C C16 0.8000(3) 1.15820(13) 0.24893(11) 0.0266(4) Uani d 0.8922(14) A 1
H H16 0.813959 1.221762 0.229232 0.032 Uiso calc 0.8922(14) A 1
C C17 0.5933(3) 1.08661(14) 0.22134(9) 0.0240(3) Uani d 0.8922(14) A 1
H H17 0.466136 1.100974 0.183733 0.029 Uiso calc 0.8922(14) A 1
C C18 0.5792(2) 0.99461(14) 0.25019(10) 0.0200(3) Uani d 0.8922(14) A 1
B B1 0.1734(3) 0.88827(13) 0.17792(10) 0.0203(3) Uani d 0.8922(14) A 1
B B2 0.0951(3) 0.71571(12) 0.22164(12) 0.0206(3) Uani d 0.8922(14) A 1
B B3 0.4808(3) 0.83321(14) 0.27939(10) 0.0202(3) Uani d 0.8922(14) A 1
N N1A -0.1999(13) 0.6816(6) 0.1539(5) 0.0194(17) Uani d 0.1078(14) A 2
H H1A -0.282(18) 0.623(4) 0.158(8) 0.023 Uiso d 0.1078(14) A 2
N N2A 0.0651(16) 0.8336(8) 0.1694(6) 0.0115(18) Uani d 0.1078(14) A 2
N N3A 0.3577(13) 1.0072(6) 0.1865(5) 0.0199(17) Uani d 0.1078(14) A 2
H H3AA 0.282922 1.041925 0.152282 0.024 Uiso calc 0.1078(14) A 2
N N4A 0.4546(15) 0.8803(7) 0.2592(6) 0.0101(16) Uani d 0.1078(14) A 2
N N5A 0.5854(14) 0.7321(6) 0.3329(6) 0.0202(18) Uani d 0.1078(14) A 2
H H5AA 0.722(10) 0.736(9) 0.366(7) 0.024 Uiso d 0.1078(14) A 2
N N6A 0.2152(19) 0.7135(6) 0.2538(6) 0.0106(17) Uani d 0.1078(14) A 2
C C1A -0.290(2) 0.7472(10) 0.1031(7) 0.014(2) Uani d 0.1078(14) A 2
C C2A -0.506(3) 0.7254(10) 0.0533(11) 0.022(3) Uani d 0.1078(14) A 2
H H2A -0.609929 0.663375 0.052168 0.026 Uiso calc 0.1078(14) A 2
C C3A -0.568(3) 0.7960(12) 0.0050(13) 0.022(3) Uani d 0.1078(14) A 2
H H3AB -0.715553 0.783290 -0.031800 0.026 Uiso calc 0.1078(14) A 2
C C4A -0.417(3) 0.8847(12) 0.0099(11) 0.017(3) Uani d 0.1078(14) A 2
H H4A -0.463478 0.933462 -0.023647 0.021 Uiso calc 0.1078(14) A 2
C C5A -0.201(2) 0.9069(10) 0.0609(9) 0.014(2) Uani d 0.1078(14) A 2
H H5AB -0.096661 0.968971 0.062466 0.017 Uiso calc 0.1078(14) A 2
C C6A -0.1419(18) 0.8371(10) 0.1089(7) 0.013(2) Uani d 0.1078(14) A 2
C C7A 0.5800(17) 1.0397(11) 0.2354(8) 0.018(2) Uani d 0.1078(14) A 2
C C8A 0.720(3) 1.1301(10) 0.2390(10) 0.025(3) Uani d 0.1078(14) A 2
H H8A 0.670904 1.178949 0.206266 0.030 Uiso calc 0.1078(14) A 2
C C9A 0.935(3) 1.1498(14) 0.2911(15) 0.020(3) Uani d 0.1078(14) A 2
H H9A 1.036852 1.213402 0.296635 0.025 Uiso calc 0.1078(14) A 2
C C10A 1.000(3) 1.0759(13) 0.3346(15) 0.025(4) Uani d 0.1078(14) A 2
H H10A 1.151947 1.089307 0.368572 0.030 Uiso calc 0.1078(14) A 2
C C11A 0.860(2) 0.9829(10) 0.3327(9) 0.020(3) Uani d 0.1078(14) A 2
H H11A 0.908625 0.933801 0.365401 0.024 Uiso calc 0.1078(14) A 2
C C12A 0.647(2) 0.9667(8) 0.2801(8) 0.012(2) Uani d 0.1078(14) A 2
C C13A 0.462(2) 0.6377(8) 0.3348(8) 0.015(2) Uani d 0.1078(14) A 2
C C14A 0.542(2) 0.5652(11) 0.3771(11) 0.018(3) Uani d 0.1078(14) A 2
H H14A 0.697182 0.574882 0.407814 0.022 Uiso calc 0.1078(14) A 2
C C15A 0.382(3) 0.4774(15) 0.3719(16) 0.019(3) Uani d 0.1078(14) A 2
H H15A 0.429636 0.425514 0.400910 0.022 Uiso calc 0.1078(14) A 2
C C16A 0.156(3) 0.4599(12) 0.3273(13) 0.020(3) Uani d 0.1078(14) A 2
H H16A 0.053894 0.397267 0.325790 0.023 Uiso calc 0.1078(14) A 2
C C17A 0.077(2) 0.5340(10) 0.2846(8) 0.016(2) Uani d 0.1078(14) A 2
H H17A -0.077468 0.524471 0.253539 0.019 Uiso calc 0.1078(14) A 2
C C18A 0.236(2) 0.6213(8) 0.2900(6) 0.0082(18) Uani d 0.1078(14) A 2
B B1A 0.0310(19) 0.7366(9) 0.1970(8) 0.011(2) Uani d 0.1078(14) A 2
B B2A 0.273(2) 0.9081(8) 0.2018(8) 0.010(2) Uani d 0.1078(14) A 2
B B3A 0.434(2) 0.7822(9) 0.2840(7) 0.012(2) Uani d 0.1078(14) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 -1.00 0.0990
0.00 1.00 1.00 0.0590
0.00 -1.00 -1.00 0.0230
0.00 1.00 -1.00 0.0670
0.00 -1.00 1.00 0.0380
0.00 0.00 -1.00 0.0440
1.00 1.00 1.00 0.1400
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
H19A C19 H19B . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C20 C19 H19A . . 109.5 ?
C20 C19 H19B . . 109.5 ?
C20 C19 H19C . . 109.5 ?
O1 C20 C19 . . 121.34(13) ?
O1 C20 C21 . . 121.53(13) ?
C21 C20 C19 . . 117.12(12) ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21B . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
H22A C22 H22B . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C23 C22 H22A . . 109.5 ?
C23 C22 H22B . . 109.5 ?
C23 C22 H22C . . 109.5 ?
O2 C23 C22 . . 122.38(13) ?
O2 C23 C24 . . 120.99(13) ?
C22 C23 C24 . . 116.61(13) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24B . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C1 N1 H1 . . 121.2(10) ?
C1 N1 B1 . . 107.84(14) ?
B1 N1 H1 . . 130.4(10) ?
C6 N2 B1 . . 106.69(14) ?
C6 N2 B2 . . 132.10(15) ?
B2 N2 B1 . . 121.21(13) ?
C7 N3 H3 . . 121.0(10) ?
C7 N3 B2 . . 107.62(14) ?
B2 N3 H3 . . 131.4(10) ?
C12 N4 B2 . . 106.30(14) ?
C12 N4 B3 . . 132.59(15) ?
B3 N4 B2 . . 121.07(12) ?
C13 N5 H5 . . 120.5(10) ?
C13 N5 B3 . . 107.76(14) ?
B3 N5 H5 . . 131.7(10) ?
C18 N6 B1 . . 132.24(15) ?
C18 N6 B3 . . 106.46(14) ?
B1 N6 B3 . . 121.25(12) ?
N1 C1 C6 . . 109.50(16) ?
C2 C1 N1 . . 129.53(19) ?
C2 C1 C6 . . 120.97(15) ?
C1 C2 H2 . . 121.1 ?
C1 C2 C3 . . 117.88(17) ?
C3 C2 H2 . . 121.1 ?
C2 C3 H3A . . 119.6 ?
C4 C3 C2 . . 120.88(17) ?
C4 C3 H3A . . 119.6 ?
C3 C4 H4 . . 119.5 ?
C3 C4 C5 . . 120.98(16) ?
C5 C4 H4 . . 119.5 ?
C4 C5 H5A . . 120.9 ?
C6 C5 C4 . . 118.26(14) ?
C6 C5 H5A . . 120.9 ?
C1 C6 N2 . . 108.71(16) ?
C5 C6 N2 . . 130.27(16) ?
C5 C6 C1 . . 121.01(13) ?
N3 C7 C12 . . 109.33(17) ?
C8 C7 N3 . . 129.57(19) ?
C8 C7 C12 . . 121.10(15) ?
C7 C8 H8 . . 120.9 ?
C7 C8 C9 . . 118.21(18) ?
C9 C8 H8 . . 120.9 ?
C8 C9 H9 . . 119.7 ?
C10 C9 C8 . . 120.5(2) ?
C10 C9 H9 . . 119.7 ?
C9 C10 H10 . . 119.4 ?
C9 C10 C11 . . 121.24(18) ?
C11 C10 H10 . . 119.4 ?
C10 C11 H11 . . 121.0 ?
C12 C11 C10 . . 118.00(15) ?
C12 C11 H11 . . 121.0 ?
C7 C12 N4 . . 108.88(17) ?
C11 C12 N4 . . 130.22(16) ?
C11 C12 C7 . . 120.88(13) ?
N5 C13 C18 . . 109.44(17) ?
C14 C13 N5 . . 129.36(19) ?
C14 C13 C18 . . 121.20(15) ?
C13 C14 H14 . . 121.2 ?
C13 C14 C15 . . 117.67(18) ?
C15 C14 H14 . . 121.2 ?
C14 C15 H15 . . 119.5 ?
C14 C15 C16 . . 121.0(2) ?
C16 C15 H15 . . 119.5 ?
C15 C16 H16 . . 119.5 ?
C17 C16 C15 . . 121.01(17) ?
C17 C16 H16 . . 119.5 ?
C16 C17 H17 . . 120.9 ?
C18 C17 C16 . . 118.20(14) ?
C18 C17 H17 . . 120.9 ?
N6 C18 C13 . . 108.64(17) ?
C17 C18 N6 . . 130.44(16) ?
C17 C18 C13 . . 120.92(13) ?
N1 B1 N2 . . 107.25(15) ?
N1 B1 N6 . . 133.95(16) ?
N6 B1 N2 . . 118.79(13) ?
N2 B2 N4 . . 118.80(13) ?
N3 B2 N2 . . 133.35(16) ?
N3 B2 N4 . . 107.85(15) ?
N4 B3 N6 . . 118.71(12) ?
N5 B3 N4 . . 133.60(16) ?
N5 B3 N6 . . 107.68(14) ?
C1A N1A H1A . . 122(8) ?
C1A N1A B1A . . 105.0(9) ?
B1A N1A H1A . . 133(8) ?
B1A N2A C6A . . 107.3(9) ?
B1A N2A B2A . . 121.9(9) ?
B2A N2A C6A . . 130.8(9) ?
C7A N3A H3AA . . 126.2 ?
C7A N3A B2A . . 107.6(10) ?
B2A N3A H3AA . . 126.2 ?
B2A N4A C12A . . 106.9(9) ?
B3A N4A C12A . . 130.8(10) ?
B3A N4A B2A . . 122.2(8) ?
C13A N5A H5AA . . 106(8) ?
C13A N5A B3A . . 107.1(9) ?
B3A N5A H5AA . . 147(8) ?
B1A N6A C18A . . 130.6(10) ?
B1A N6A B3A . . 122.9(9) ?
B3A N6A C18A . . 106.5(9) ?
C2A C1A N1A . . 123.9(12) ?
C6A C1A N1A . . 113.6(10) ?
C6A C1A C2A . . 122.5(10) ?
C1A C2A H2A . . 121.3 ?
C1A C2A C3A . . 117.3(12) ?
C3A C2A H2A . . 121.3 ?
C2A C3A H3AB . . 120.2 ?
C4A C3A C2A . . 119.7(13) ?
C4A C3A H3AB . . 120.2 ?
C3A C4A H4A . . 118.6 ?
C3A C4A C5A . . 122.8(14) ?
C5A C4A H4A . . 118.6 ?
C4A C5A H5AB . . 121.4 ?
C6A C5A C4A . . 117.2(13) ?
C6A C5A H5AB . . 121.4 ?
C1A C6A N2A . . 106.6(10) ?
C5A C6A N2A . . 132.9(12) ?
C5A C6A C1A . . 120.4(10) ?
C8A C7A N3A . . 126.1(13) ?
C8A C7A C12A . . 122.4(10) ?
C12A C7A N3A . . 111.4(11) ?
C7A C8A H8A . . 120.7 ?
C7A C8A C9A . . 118.5(12) ?
C9A C8A H8A . . 120.7 ?
C8A C9A H9A . . 120.9 ?
C10A C9A C8A . . 118.3(15) ?
C10A C9A H9A . . 120.9 ?
C9A C10A H10A . . 117.7 ?
C9A C10A C11A . . 124.6(16) ?
C11A C10A H10A . . 117.7 ?
C10A C11A H11A . . 122.5 ?
C12A C11A C10A . . 115.0(13) ?
C12A C11A H11A . . 122.5 ?
C7A C12A N4A . . 106.8(11) ?
C7A C12A C11A . . 121.1(10) ?
C11A C12A N4A . . 132.1(12) ?
N5A C13A C18A . . 112.6(11) ?
C14A C13A N5A . . 126.2(13) ?
C14A C13A C18A . . 121.1(9) ?
C13A C14A H14A . . 122.4 ?
C13A C14A C15A . . 115.3(12) ?
C15A C14A H14A . . 122.4 ?
C14A C15A H15A . . 117.9 ?
C14A C15A C16A . . 124.2(16) ?
C16A C15A H15A . . 117.9 ?
C15A C16A H16A . . 120.1 ?
C15A C16A C17A . . 119.9(15) ?
C17A C16A H16A . . 120.1 ?
C16A C17A H17A . . 122.0 ?
C18A C17A C16A . . 116.0(12) ?
C18A C17A H17A . . 122.0 ?
C13A C18A N6A . . 105.6(10) ?
C17A C18A N6A . . 130.9(12) ?
C17A C18A C13A . . 123.5(9) ?
N2A B1A N1A . . 107.4(9) ?
N6A B1A N1A . . 134.6(11) ?
N6A B1A N2A . . 118.0(9) ?
N2A B2A N4A . . 117.6(8) ?
N3A B2A N2A . . 135.0(11) ?
N3A B2A N4A . . 107.2(9) ?
N4A B3A N6A . . 117.2(8) ?
N5A B3A N4A . . 134.7(10) ?
N5A B3A N6A . . 108.1(9) ?
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
O1 C20 . 1.2110(15) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C19 C20 . 1.4927(18) ?
C20 C21 . 1.4906(19) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
O2 C23 . 1.2122(16) ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
C22 C23 . 1.4873(18) ?
C23 C24 . 1.494(2) ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 0.9800 ?
N1 H1 . 0.874(12) ?
N1 C1 . 1.3948(18) ?
N1 B1 . 1.4247(19) ?
N2 C6 . 1.4082(17) ?
N2 B1 . 1.459(2) ?
N2 B2 . 1.429(2) ?
N3 H3 . 0.886(12) ?
N3 C7 . 1.3985(17) ?
N3 B2 . 1.4212(19) ?
N4 C12 . 1.4091(18) ?
N4 B2 . 1.459(2) ?
N4 B3 . 1.433(2) ?
N5 H5 . 0.871(12) ?
N5 C13 . 1.3941(17) ?
N5 B3 . 1.4191(18) ?
N6 C18 . 1.4077(18) ?
N6 B1 . 1.428(2) ?
N6 B3 . 1.459(2) ?
C1 C2 . 1.388(2) ?
C1 C6 . 1.405(2) ?
C2 H2 . 0.9500 ?
C2 C3 . 1.403(2) ?
C3 H3A . 0.9500 ?
C3 C4 . 1.392(2) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.397(2) ?
C5 H5A . 0.9500 ?
C5 C6 . 1.382(2) ?
C7 C8 . 1.382(3) ?
C7 C12 . 1.409(2) ?
C8 H8 . 0.9500 ?
C8 C9 . 1.399(3) ?
C9 H9 . 0.9500 ?
C9 C10 . 1.396(2) ?
C10 H10 . 0.9500 ?
C10 C11 . 1.399(2) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.382(2) ?
C13 C14 . 1.392(3) ?
C13 C18 . 1.410(2) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.397(2) ?
C15 H15 . 0.9500 ?
C15 C16 . 1.400(2) ?
C16 H16 . 0.9500 ?
C16 C17 . 1.398(2) ?
C17 H17 . 0.9500 ?
C17 C18 . 1.379(2) ?
N1A H1A . 0.880(18) ?
N1A C1A . 1.391(11) ?
N1A B1A . 1.460(12) ?
N2A C6A . 1.447(11) ?
N2A B1A . 1.433(12) ?
N2A B2A . 1.433(12) ?
N3A H3AA . 0.8800 ?
N3A C7A . 1.389(11) ?
N3A B2A . 1.419(11) ?
N4A C12A . 1.454(11) ?
N4A B2A . 1.433(13) ?
N4A B3A . 1.429(12) ?
N5A H5AA . 0.883(18) ?
N5A C13A . 1.370(11) ?
N5A B3A . 1.414(11) ?
N6A C18A . 1.459(11) ?
N6A B1A . 1.409(12) ?
N6A B3A . 1.435(12) ?
C1A C2A . 1.362(13) ?
C1A C6A . 1.359(13) ?
C2A H2A . 0.9500 ?
C2A C3A . 1.363(14) ?
C3A H3AB . 0.9500 ?
C3A C4A . 1.356(14) ?
C4A H4A . 0.9500 ?
C4A C5A . 1.369(13) ?
C5A H5AB . 0.9500 ?
C5A C6A . 1.346(12) ?
C7A C8A . 1.349(13) ?
C7A C12A . 1.367(13) ?
C8A H8A . 0.9500 ?
C8A C9A . 1.371(15) ?
C9A H9A . 0.9500 ?
C9A C10A . 1.363(15) ?
C10A H10A . 0.9500 ?
C10A C11A . 1.382(13) ?
C11A H11A . 0.9500 ?
C11A C12A . 1.370(13) ?
C13A C14A . 1.369(14) ?
C13A C18A . 1.382(13) ?
C14A H14A . 0.9500 ?
C14A C15A . 1.375(15) ?
C15A H15A . 0.9500 ?
C15A C16A . 1.378(15) ?
C16A H16A . 0.9500 ?
C16A C17A . 1.387(12) ?
C17A H17A . 0.9500 ?
C17A C18A . 1.365(13) ?
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
_geom_hbond_publ_flag
N3 H3 O2 . 0.886(12) 2.133(13) 2.9817(14) 160.3(14) yes
N5 H5 O1 . 0.871(12) 2.086(13) 2.9544(15) 174.6(14) yes
N1A H1A O2 . 0.880(18) 2.27(4) 3.133(8) 165(11) yes
N5A H5AA O1 . 0.883(18) 2.19(5) 3.026(8) 158(11) 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_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 . . . . -178.74(15) ?
N1 C1 C6 N2 . . . . -0.09(15) ?
N1 C1 C6 C5 . . . . 178.83(11) ?
N3 C7 C8 C9 . . . . 178.04(17) ?
N3 C7 C12 N4 . . . . 1.36(14) ?
N3 C7 C12 C11 . . . . -177.48(11) ?
N5 C13 C14 C15 . . . . 178.95(17) ?
N5 C13 C18 N6 . . . . 0.09(14) ?
N5 C13 C18 C17 . . . . -179.75(11) ?
C1 N1 B1 N2 . . . . 0.79(14) ?
C1 N1 B1 N6 . . . . -179.44(14) ?
C1 C2 C3 C4 . . . . -0.9(2) ?
C2 C1 C6 N2 . . . . 179.59(13) ?
C2 C1 C6 C5 . . . . -1.5(2) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
C3 C4 C5 C6 . . . . 0.2(2) ?
C4 C5 C6 N2 . . . . 179.21(13) ?
C4 C5 C6 C1 . . . . 0.55(19) ?
C6 N2 B1 N1 . . . . -0.83(14) ?
C6 N2 B1 N6 . . . . 179.35(11) ?
C6 N2 B2 N3 . . . . -2.1(3) ?
C6 N2 B2 N4 . . . . 176.60(12) ?
C6 C1 C2 C3 . . . . 1.7(2) ?
C7 N3 B2 N2 . . . . 178.35(14) ?
C7 N3 B2 N4 . . . . -0.47(14) ?
C7 C8 C9 C10 . . . . 0.1(3) ?
C8 C7 C12 N4 . . . . -178.79(13) ?
C8 C7 C12 C11 . . . . 2.4(2) ?
C8 C9 C10 C11 . . . . 1.1(3) ?
C9 C10 C11 C12 . . . . -0.5(2) ?
C10 C11 C12 N4 . . . . -179.74(14) ?
C10 C11 C12 C7 . . . . -1.2(2) ?
C12 N4 B2 N2 . . . . -177.75(11) ?
C12 N4 B2 N3 . . . . 1.27(14) ?
C12 N4 B3 N5 . . . . -0.4(2) ?
C12 N4 B3 N6 . . . . -179.55(12) ?
C12 C7 C8 C9 . . . . -1.8(2) ?
C13 N5 B3 N4 . . . . 179.53(14) ?
C13 N5 B3 N6 . . . . -1.21(14) ?
C13 C14 C15 C16 . . . . 0.6(3) ?
C14 C13 C18 N6 . . . . 179.70(14) ?
C14 C13 C18 C17 . . . . -0.1(2) ?
C14 C15 C16 C17 . . . . 0.0(3) ?
C15 C16 C17 C18 . . . . -0.7(2) ?
C16 C17 C18 N6 . . . . -179.02(13) ?
C16 C17 C18 C13 . . . . 0.78(19) ?
C18 N6 B1 N1 . . . . 0.6(2) ?
C18 N6 B1 N2 . . . . -179.62(12) ?
C18 N6 B3 N4 . . . . -179.36(11) ?
C18 N6 B3 N5 . . . . 1.26(13) ?
C18 C13 C14 C15 . . . . -0.6(3) ?
B1 N1 C1 C2 . . . . 179.91(15) ?
B1 N1 C1 C6 . . . . -0.45(14) ?
B1 N2 C6 C1 . . . . 0.57(14) ?
B1 N2 C6 C5 . . . . -178.21(13) ?
B1 N2 B2 N3 . . . . 178.83(14) ?
B1 N2 B2 N4 . . . . -2.45(18) ?
B1 N6 C18 C13 . . . . -178.00(13) ?
B1 N6 C18 C17 . . . . 1.8(2) ?
B1 N6 B3 N4 . . . . -1.81(18) ?
B1 N6 B3 N5 . . . . 178.81(11) ?
B2 N2 C6 C1 . . . . -178.58(13) ?
B2 N2 C6 C5 . . . . 2.6(2) ?
B2 N2 B1 N1 . . . . 178.43(11) ?
B2 N2 B1 N6 . . . . -1.38(18) ?
B2 N3 C7 C8 . . . . 179.63(15) ?
B2 N3 C7 C12 . . . . -0.53(14) ?
B2 N4 C12 C7 . . . . -1.60(13) ?
B2 N4 C12 C11 . . . . 177.09(13) ?
B2 N4 B3 N5 . . . . 177.03(13) ?
B2 N4 B3 N6 . . . . -2.16(18) ?
B3 N4 C12 C7 . . . . 176.07(12) ?
B3 N4 C12 C11 . . . . -5.2(2) ?
B3 N4 B2 N2 . . . . 4.25(18) ?
B3 N4 B2 N3 . . . . -176.73(11) ?
B3 N5 C13 C14 . . . . -178.86(16) ?
B3 N5 C13 C18 . . . . 0.71(14) ?
B3 N6 C18 C13 . . . . -0.83(14) ?
B3 N6 C18 C17 . . . . 178.99(13) ?
B3 N6 B1 N1 . . . . -176.20(13) ?
B3 N6 B1 N2 . . . . 3.55(18) ?
N1A C1A C2A C3A . . . . -178.3(14) ?
N1A C1A C6A N2A . . . . -0.7(14) ?
N1A C1A C6A C5A . . . . 177.6(11) ?
N3A C7A C8A C9A . . . . 179.9(15) ?
N3A C7A C12A N4A . . . . -0.1(13) ?
N3A C7A C12A C11A . . . . -179.9(11) ?
N5A C13A C14A C15A . . . . 177.8(15) ?
N5A C13A C18A N6A . . . . 1.8(12) ?
N5A C13A C18A C17A . . . . -178.2(10) ?
C1A N1A B1A N2A . . . . 0.4(12) ?
C1A N1A B1A N6A . . . . -177.3(13) ?
C1A C2A C3A C4A . . . . -2(3) ?
C2A C1A C6A N2A . . . . 178.1(12) ?
C2A C1A C6A C5A . . . . -4(2) ?
C2A C3A C4A C5A . . . . 1(3) ?
C3A C4A C5A C6A . . . . -1(2) ?
C4A C5A C6A N2A . . . . -179.6(13) ?
C4A C5A C6A C1A . . . . 3(2) ?
C6A N2A B1A N1A . . . . -0.9(12) ?
C6A N2A B1A N6A . . . . 177.3(9) ?
C6A N2A B2A N3A . . . . -2(2) ?
C6A N2A B2A N4A . . . . -177.4(10) ?
C6A C1A C2A C3A . . . . 3(2) ?
C7A N3A B2A N2A . . . . -177.2(12) ?
C7A N3A B2A N4A . . . . -1.9(12) ?
C7A C8A C9A C10A . . . . 2(3) ?
C8A C7A C12A N4A . . . . -179.0(12) ?
C8A C7A C12A C11A . . . . 1(2) ?
C8A C9A C10A C11A . . . . -2(3) ?
C9A C10A C11A C12A . . . . 2(3) ?
C10A C11A C12A N4A . . . . 178.8(15) ?
C10A C11A C12A C7A . . . . -2(2) ?
C12A N4A B2A N2A . . . . 178.1(9) ?
C12A N4A B2A N3A . . . . 1.9(11) ?
C12A N4A B3A N5A . . . . -3(2) ?
C12A N4A B3A N6A . . . . 178.5(9) ?
C12A C7A C8A C9A . . . . -1(2) ?
C13A N5A B3A N4A . . . . 179.4(12) ?
C13A N5A B3A N6A . . . . -1.8(12) ?
C13A C14A C15A C16A . . . . 1(3) ?
C14A C13A C18A N6A . . . . -179.7(12) ?
C14A C13A C18A C17A . . . . 0(2) ?
C14A C15A C16A C17A . . . . -1(3) ?
C15A C16A C17A C18A . . . . 0(2) ?
C16A C17A C18A N6A . . . . 179.9(13) ?
C16A C17A C18A C13A . . . . -0.1(19) ?
C18A N6A B1A N1A . . . . 0(2) ?
C18A N6A B1A N2A . . . . -177.5(9) ?
C18A N6A B3A N4A . . . . -178.1(9) ?
C18A N6A B3A N5A . . . . 2.8(11) ?
C18A C13A C14A C15A . . . . -1(2) ?
B1A N1A C1A C2A . . . . -178.6(13) ?
B1A N1A C1A C6A . . . . 0.2(13) ?
B1A N2A C6A C1A . . . . 1.0(13) ?
B1A N2A C6A C5A . . . . -177.0(14) ?
B1A N2A B2A N3A . . . . 178.8(12) ?
B1A N2A B2A N4A . . . . 3.8(16) ?
B1A N6A C18A C13A . . . . 174.6(11) ?
B1A N6A C18A C17A . . . . -5.4(19) ?
B1A N6A B3A N4A . . . . 4.2(16) ?
B1A N6A B3A N5A . . . . -174.8(9) ?
B2A N2A C6A C1A . . . . -178.0(11) ?
B2A N2A C6A C5A . . . . 4(2) ?
B2A N2A B1A N1A . . . . 178.2(9) ?
B2A N2A B1A N6A . . . . -3.7(16) ?
B2A N3A C7A C8A . . . . -179.9(13) ?
B2A N3A C7A C12A . . . . 1.3(13) ?
B2A N4A C12A C7A . . . . -1.1(12) ?
B2A N4A C12A C11A . . . . 178.6(13) ?
B2A N4A B3A N5A . . . . 174.7(11) ?
B2A N4A B3A N6A . . . . -4.0(15) ?
B3A N4A C12A C7A . . . . 176.6(11) ?
B3A N4A C12A C11A . . . . -4(2) ?
B3A N4A B2A N2A . . . . 0.2(15) ?
B3A N4A B2A N3A . . . . -176.1(9) ?
B3A N5A C13A C14A . . . . -178.4(13) ?
B3A N5A C13A C18A . . . . 0.0(13) ?
B3A N6A C18A C13A . . . . -2.8(11) ?
B3A N6A C18A C17A . . . . 177.2(12) ?
B3A N6A B1A N1A . . . . 177.0(11) ?
B3A N6A B1A N2A . . . . -0.5(16) ?
