#------------------------------------------------------------------------------
#$Date: 2020-03-19 01:49:32 +0200 (Thu, 19 Mar 2020) $
#$Revision: 249501 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/44/4134446.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_4134446
loop_
_publ_author_name
'Suresh, Subeesh Madayanad'
'Duda, Eimantas'
'Hall, David'
'Yao, Zhen'
'Bagnich, Sergey'
'Slawin, Alexandra M. Z.'
'Bässler, Heinz'
'Beljonne, David'
'Buck, Manfred'
'Olivier, Yoann'
'Köhler, Anna'
'Zysman-Colman, Eli'
_publ_section_title
;
 A Deep Blue B,N-Doped Heptacene Emitter That Shows Both Thermally
 Activated Delayed Fluorescence and Delayed Fluores-cence by Triplet
 Triplet Annihilation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13704
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C55 H56 B3 N3 O5'
_chemical_formula_sum            'C55 H56 B3 N3 O5'
_chemical_formula_weight         871.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-20
_audit_creation_method           'by CrystalStructure 4.3'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.74368(15)
_cell_length_b                   18.5497(3)
_cell_length_c                   26.3997(5)
_cell_measurement_reflns_used    18743
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.82
_cell_measurement_theta_min      2.89
_cell_volume                     4771.54(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            51012
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         2.911
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1848.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details
;
 Flack x determined using 3101 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     612
_refine_ls_number_reflns         8665
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0638P)²+0.3827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                7681
_reflns_number_total             8665
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja9b13704_si_002.cif
_cod_data_source_block           3BNOH
_cod_database_code               4134446
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-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
O1 O 0.6563(3) 1.04695(10) 0.63081(8) 0.0664(6) Uani 1 1 d D . . . .
O23 O 0.8844(3) 0.49292(12) 0.75265(8) 0.0791(7) Uani 1 1 d D . . . .
O27 O 0.7625(3) 0.77788(10) 0.70937(7) 0.0600(5) Uani 1 1 d D . . . .
O61 O 0.6374(4) 0.99258(18) 0.72734(10) 0.1046(10) Uani 1 1 d . . . . .
O66 O 0.7386(2) 0.68647(13) 0.79872(8) 0.0745(6) Uani 1 1 d . . . . .
N8 N 0.7059(2) 0.94235(10) 0.48831(7) 0.0404(4) Uani 1 1 d . . . . .
N12 N 0.7511(2) 0.70493(9) 0.55618(7) 0.0378(4) Uani 1 1 d . . . . .
N16 N 0.7787(2) 0.45448(10) 0.59868(8) 0.0430(5) Uani 1 1 d . . . . .
C2 C 0.6623(2) 1.05238(13) 0.53647(10) 0.0425(5) Uani 1 1 d . . . . .
C3 C 0.6353(3) 1.12696(13) 0.53496(11) 0.0488(6) Uani 1 1 d . . . . .
H3 H 0.625438 1.151984 0.566144 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6226(3) 1.16549(14) 0.49056(11) 0.0536(6) Uani 1 1 d . . . . .
C5 C 0.6388(3) 1.12775(14) 0.44511(11) 0.0533(6) Uani 1 1 d . . . . .
H5 H 0.629776 1.152938 0.413959 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6675(3) 1.05508(13) 0.44426(10) 0.0477(6) Uani 1 1 d . . . . .
H6 H 0.679630 1.030895 0.412854 0.057 Uiso 1 1 calc R U . . .
C7 C 0.6789(2) 1.01674(12) 0.49013(10) 0.0401(5) Uani 1 1 d . . . . .
C9 C 0.7155(2) 0.89938(12) 0.53167(9) 0.0378(5) Uani 1 1 d . . . . .
C10 C 0.7340(2) 0.82544(12) 0.52483(9) 0.0383(5) Uani 1 1 d . . . . .
H10 H 0.740440 0.806427 0.491503 0.046 Uiso 1 1 calc R U . . .
C11 C 0.7433(2) 0.77930(12) 0.56607(9) 0.0362(5) Uani 1 1 d . . . . .
C13 C 0.7671(2) 0.65312(12) 0.59391(8) 0.0358(5) Uani 1 1 d . . . . .
C14 C 0.7645(2) 0.58074(12) 0.57943(9) 0.0386(5) Uani 1 1 d . . . . .
H14 H 0.747639 0.568500 0.545043 0.046 Uiso 1 1 calc R U . . .
C15 C 0.7863(2) 0.52634(12) 0.61481(9) 0.0385(5) Uani 1 1 d . . . . .
C17 C 0.8118(2) 0.39547(13) 0.62959(10) 0.0442(5) Uani 1 1 d . . . . .
C18 C 0.8054(3) 0.32577(14) 0.60941(12) 0.0541(6) Uani 1 1 d . . . . .
H18 H 0.777226 0.318910 0.575295 0.065 Uiso 1 1 calc R U . . .
C19 C 0.8396(3) 0.26715(15) 0.63871(12) 0.0582(7) Uani 1 1 d . . . . .
H19 H 0.833870 0.220289 0.624359 0.070 Uiso 1 1 calc R U . . .
C20 C 0.8823(3) 0.27440(15) 0.68873(12) 0.0557(7) Uani 1 1 d . . . . .
C21 C 0.8881(3) 0.34303(16) 0.70825(11) 0.0570(7) Uani 1 1 d . . . . .
H21 H 0.917565 0.348938 0.742302 0.068 Uiso 1 1 calc R U . . .
C22 C 0.8524(3) 0.40531(14) 0.68031(10) 0.0488(6) Uani 1 1 d . . . . .
C24 C 0.8168(3) 0.54319(13) 0.66586(9) 0.0425(5) Uani 1 1 d . . . . .
C25 C 0.8109(2) 0.61658(13) 0.67900(9) 0.0426(5) Uani 1 1 d . . . . .
H25 H 0.826454 0.628795 0.713474 0.051 Uiso 1 1 calc R U . . .
C26 C 0.7839(2) 0.67280(12) 0.64543(9) 0.0391(5) Uani 1 1 d . . . . .
C28 C 0.7430(2) 0.80603(12) 0.61629(9) 0.0390(5) Uani 1 1 d . . . . .
C29 C 0.7224(2) 0.88038(12) 0.62150(9) 0.0409(5) Uani 1 1 d . . . . .
H29 H 0.719720 0.899455 0.654881 0.049 Uiso 1 1 calc R U . . .
C30 C 0.7055(2) 0.92878(12) 0.58124(9) 0.0397(5) Uani 1 1 d . . . . .
C31 C 0.5890(4) 1.24517(16) 0.49040(14) 0.0760(10) Uani 1 1 d . . . . .
H31A H 0.669484 1.272501 0.479124 0.091 Uiso 1 1 calc R U . . .
H31B H 0.563640 1.260397 0.524691 0.091 Uiso 1 1 calc R U . . .
H31C H 0.512223 1.254187 0.467284 0.091 Uiso 1 1 calc R U . . .
C32 C 0.7408(2) 0.90975(12) 0.44033(9) 0.0391(5) Uani 1 1 d . . . . .
C33 C 0.8771(2) 0.90836(14) 0.42569(10) 0.0446(5) Uani 1 1 d . . . . .
H33 H 0.944445 0.932821 0.445224 0.054 Uiso 1 1 calc R U . . .
C34 C 0.9146(3) 0.87138(16) 0.38271(10) 0.0525(6) Uani 1 1 d . . . . .
H34 H 1.008116 0.871288 0.372573 0.063 Uiso 1 1 calc R U . . .
C35 C 0.8194(3) 0.83437(17) 0.35393(10) 0.0563(7) Uani 1 1 d . . . . .
C36 C 0.6826(3) 0.83799(18) 0.36830(10) 0.0575(7) Uani 1 1 d . . . . .
H36 H 0.615017 0.814237 0.348436 0.069 Uiso 1 1 calc R U . . .
C37 C 0.6429(2) 0.87578(15) 0.41123(10) 0.0495(6) Uani 1 1 d . . . . .
H37 H 0.548814 0.878210 0.420500 0.059 Uiso 1 1 calc R U . . .
C38 C 0.8657(4) 0.7915(3) 0.30844(15) 0.0968(14) Uani 1 1 d . . . . .
H38A H 0.878060 0.823947 0.279503 0.116 Uiso 1 1 calc R U . . .
H38B H 0.796172 0.755180 0.300154 0.116 Uiso 1 1 calc R U . . .
H38C H 0.952865 0.767523 0.316117 0.116 Uiso 1 1 calc R U . . .
C39 C 0.7403(2) 0.68134(11) 0.50436(8) 0.0365(5) Uani 1 1 d . . . . .
C40 C 0.8573(3) 0.66932(14) 0.47635(10) 0.0482(6) Uani 1 1 d . . . . .
H40 H 0.945245 0.677386 0.490830 0.058 Uiso 1 1 calc R U . . .
C41 C 0.8455(3) 0.64531(17) 0.42678(11) 0.0617(8) Uani 1 1 d . . . . .
H41 H 0.926163 0.636875 0.407483 0.074 Uiso 1 1 calc R U . . .
C42 C 0.7180(4) 0.63335(16) 0.40480(11) 0.0614(8) Uani 1 1 d . . . . .
C43 C 0.6025(3) 0.64657(16) 0.43380(11) 0.0568(7) Uani 1 1 d . . . . .
H43 H 0.514286 0.638979 0.419401 0.068 Uiso 1 1 calc R U . . .
C44 C 0.6123(3) 0.67049(13) 0.48310(10) 0.0436(5) Uani 1 1 d . . . . .
H44 H 0.531633 0.679448 0.502328 0.052 Uiso 1 1 calc R U . . .
C45 C 0.7052(6) 0.6065(3) 0.35117(14) 0.1078(16) Uani 1 1 d . . . . .
H45A H 0.626651 0.629875 0.334794 0.129 Uiso 1 1 calc R U . . .
H45B H 0.691492 0.554204 0.351376 0.129 Uiso 1 1 calc R U . . .
H45C H 0.789229 0.618089 0.332442 0.129 Uiso 1 1 calc R U . . .
C46 C 0.7239(2) 0.44173(11) 0.54861(9) 0.0411(5) Uani 1 1 d . . . . .
C47 C 0.8076(3) 0.44367(13) 0.50660(10) 0.0484(6) Uani 1 1 d . . . . .
H47 H 0.904077 0.448642 0.510525 0.058 Uiso 1 1 calc R U . . .
C48 C 0.7508(3) 0.43836(14) 0.45855(11) 0.0538(6) Uani 1 1 d . . . . .
H48 H 0.809009 0.440503 0.429705 0.065 Uiso 1 1 calc R U . . .
C49 C 0.6104(3) 0.42997(14) 0.45194(11) 0.0548(7) Uani 1 1 d . . . . .
C50 C 0.5286(3) 0.42526(15) 0.49474(12) 0.0566(7) Uani 1 1 d . . . . .
H50 H 0.432827 0.417393 0.491012 0.068 Uiso 1 1 calc R U . . .
C51 C 0.5836(3) 0.43179(13) 0.54262(11) 0.0483(6) Uani 1 1 d . . . . .
H51 H 0.525620 0.429487 0.571495 0.058 Uiso 1 1 calc R U . . .
C52 C 0.5475(4) 0.4259(2) 0.40003(14) 0.0846(11) Uani 1 1 d . . . . .
H52A H 0.502099 0.471739 0.392194 0.101 Uiso 1 1 calc R U . . .
H52B H 0.479937 0.386823 0.399109 0.101 Uiso 1 1 calc R U . . .
H52C H 0.619462 0.416614 0.374929 0.101 Uiso 1 1 calc R U . . .
C53 C 0.9205(4) 0.20827(17) 0.71934(14) 0.0724(9) Uani 1 1 d . . . . .
H53A H 0.996035 0.182827 0.702576 0.087 Uiso 1 1 calc R U . . .
H53B H 0.840834 0.176208 0.721858 0.087 Uiso 1 1 calc R U . . .
H53C H 0.949248 0.222992 0.753370 0.087 Uiso 1 1 calc R U . . .
C62 C 0.5280(7) 0.9566(5) 0.7483(3) 0.155(3) Uani 1 1 d . . . . .
H62A H 0.508391 0.912280 0.728676 0.187 Uiso 1 1 calc R U . . .
H62B H 0.445266 0.987578 0.747603 0.187 Uiso 1 1 calc R U . . .
C63 C 0.5615(12) 0.9388(6) 0.7985(4) 0.216(5) Uani 1 1 d . . . . .
H63A H 0.543507 0.887068 0.804774 0.259 Uiso 1 1 calc R U . . .
H63B H 0.505492 0.967578 0.822327 0.259 Uiso 1 1 calc R U . . .
C64 C 0.7026(14) 0.9542(5) 0.8053(3) 0.214(6) Uani 1 1 d . . . . .
H64A H 0.754008 0.909315 0.812650 0.257 Uiso 1 1 calc R U . . .
H64B H 0.715396 0.987898 0.833998 0.257 Uiso 1 1 calc R U . . .
C65 C 0.7506(8) 0.9859(4) 0.7595(2) 0.156(3) Uani 1 1 d . . . . .
H65A H 0.791268 1.033826 0.766343 0.187 Uiso 1 1 calc R U . . .
H65B H 0.821561 0.954965 0.743713 0.187 Uiso 1 1 calc R U . . .
C67 C 0.6092(4) 0.6502(2) 0.80150(15) 0.0792(10) Uani 1 1 d . . . . .
H67A H 0.617236 0.605305 0.821553 0.095 Uiso 1 1 calc R U . . .
H67B H 0.575566 0.637900 0.767178 0.095 Uiso 1 1 calc R U . . .
C68 C 0.5151(4) 0.7016(3) 0.82653(18) 0.0959(13) Uani 1 1 d . . . . .
H68A H 0.438109 0.676216 0.843292 0.115 Uiso 1 1 calc R U . . .
H68B H 0.477711 0.736916 0.802024 0.115 Uiso 1 1 calc R U . . .
C69 C 0.6074(5) 0.7379(3) 0.86493(17) 0.0986(13) Uani 1 1 d . . . . .
H69A H 0.576074 0.787604 0.872093 0.118 Uiso 1 1 calc R U . . .
H69B H 0.610035 0.710287 0.897017 0.118 Uiso 1 1 calc R U . . .
C70 C 0.7455(4) 0.7380(2) 0.83951(14) 0.0866(11) Uani 1 1 d . . . . .
H70A H 0.766734 0.786618 0.826160 0.104 Uiso 1 1 calc R U . . .
H70B H 0.817983 0.724184 0.863926 0.104 Uiso 1 1 calc R U . . .
B1 B 0.6744(3) 1.00999(15) 0.58663(11) 0.0446(6) Uani 1 1 d . . . . .
B23 B 0.8536(3) 0.48213(18) 0.70265(12) 0.0523(7) Uani 1 1 d . . . . .
B27 B 0.7647(3) 0.75315(15) 0.66063(10) 0.0423(6) Uani 1 1 d . . . . .
H1 H 0.653(4) 1.0192(17) 0.6623(8) 0.087(12) Uiso 1 1 d D . . . .
H27 H 0.766(5) 0.7420(17) 0.7365(11) 0.110(14) Uiso 1 1 d D . . . .
H23 H 0.893(5) 0.5439(8) 0.7615(17) 0.114(15) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0090 0.0039
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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 H1 118(2) . . ?
B23 O23 H23 113(3) . . ?
B27 O27 H27 117(3) . . ?
C62 O61 C65 109.0(5) . . ?
C67 O66 C70 108.3(3) . . ?
C9 N8 C7 122.97(19) . . ?
C9 N8 C32 117.63(18) . . ?
C7 N8 C32 119.02(18) . . ?
C13 N12 C11 123.39(19) . . ?
C13 N12 C39 118.54(17) . . ?
C11 N12 C39 118.07(18) . . ?
C15 N16 C17 123.6(2) . . ?
C15 N16 C46 116.95(18) . . ?
C17 N16 C46 119.3(2) . . ?
C7 C2 C3 117.4(2) . . ?
C7 C2 B1 120.0(2) . . ?
C3 C2 B1 122.6(2) . . ?
C4 C3 C2 123.4(3) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
C3 C4 C5 117.4(2) . . ?
C3 C4 C31 121.9(3) . . ?
C5 C4 C31 120.7(3) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 N8 121.0(2) . . ?
C2 C7 C6 120.3(2) . . ?
N8 C7 C6 118.7(2) . . ?
C10 C9 N8 117.6(2) . . ?
C10 C9 C30 120.4(2) . . ?
N8 C9 C30 122.05(19) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 N12 117.6(2) . . ?
C10 C11 C28 121.2(2) . . ?
N12 C11 C28 121.2(2) . . ?
N12 C13 C14 117.8(2) . . ?
N12 C13 C26 121.43(19) . . ?
C14 C13 C26 120.8(2) . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 N16 118.5(2) . . ?
C14 C15 C24 120.7(2) . . ?
N16 C15 C24 120.7(2) . . ?
C18 C17 N16 119.3(2) . . ?
C18 C17 C22 119.6(2) . . ?
N16 C17 C22 121.1(2) . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 122.0(3) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 117.2(3) . . ?
C21 C20 C53 122.7(3) . . ?
C19 C20 C53 120.1(3) . . ?
C20 C21 C22 123.4(3) . . ?
C20 C21 H21 118.3 . . ?
C22 C21 H21 118.3 . . ?
C17 C22 C21 117.3(3) . . ?
C17 C22 B23 119.1(2) . . ?
C21 C22 B23 123.6(3) . . ?
C25 C24 C15 116.1(2) . . ?
C25 C24 B23 124.6(2) . . ?
C15 C24 B23 119.3(2) . . ?
C26 C25 C24 125.1(2) . . ?
C26 C25 H25 117.4 . . ?
C24 C25 H25 117.4 . . ?
C25 C26 C13 116.1(2) . . ?
C25 C26 B27 125.2(2) . . ?
C13 C26 B27 118.7(2) . . ?
C29 C28 C11 115.9(2) . . ?
C29 C28 B27 124.9(2) . . ?
C11 C28 B27 119.2(2) . . ?
C28 C29 C30 125.0(2) . . ?
C28 C29 H29 117.5 . . ?
C30 C29 H29 117.5 . . ?
C29 C30 C9 116.4(2) . . ?
C29 C30 B1 125.4(2) . . ?
C9 C30 B1 118.2(2) . . ?
C4 C31 H31A 109.5 . . ?
C4 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C4 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C37 C32 C33 120.0(2) . . ?
C37 C32 N8 121.2(2) . . ?
C33 C32 N8 118.6(2) . . ?
C34 C33 C32 119.7(2) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 121.6(2) . . ?
C33 C34 H34 119.2 . . ?
C35 C34 H34 119.2 . . ?
C34 C35 C36 118.1(2) . . ?
C34 C35 C38 119.9(3) . . ?
C36 C35 C38 122.0(3) . . ?
C37 C36 C35 121.0(3) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C32 C37 C36 119.6(2) . . ?
C32 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C44 120.4(2) . . ?
C40 C39 N12 119.9(2) . . ?
C44 C39 N12 119.7(2) . . ?
C39 C40 C41 119.3(2) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C40 C41 C42 121.3(3) . . ?
C40 C41 H41 119.3 . . ?
C42 C41 H41 119.3 . . ?
C43 C42 C41 117.9(2) . . ?
C43 C42 C45 120.8(3) . . ?
C41 C42 C45 121.3(3) . . ?
C44 C43 C42 121.6(3) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C39 119.5(2) . . ?
C43 C44 H44 120.2 . . ?
C39 C44 H44 120.2 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 C51 119.7(2) . . ?
C47 C46 N16 120.9(2) . . ?
C51 C46 N16 119.3(2) . . ?
C46 C47 C48 119.9(2) . . ?
C46 C47 H47 120.1 . . ?
C48 C47 H47 120.1 . . ?
C47 C48 C49 121.1(3) . . ?
C47 C48 H48 119.5 . . ?
C49 C48 H48 119.5 . . ?
C50 C49 C48 118.1(3) . . ?
C50 C49 C52 120.4(3) . . ?
C48 C49 C52 121.5(3) . . ?
C51 C50 C49 121.2(2) . . ?
C51 C50 H50 119.4 . . ?
C49 C50 H50 119.4 . . ?
C50 C51 C46 119.9(3) . . ?
C50 C51 H51 120.0 . . ?
C46 C51 H51 120.0 . . ?
C49 C52 H52A 109.5 . . ?
C49 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C49 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C20 C53 H53A 109.5 . . ?
C20 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C20 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O61 C62 C63 108.2(7) . . ?
O61 C62 H62A 110.1 . . ?
C63 C62 H62A 110.1 . . ?
O61 C62 H62B 110.1 . . ?
C63 C62 H62B 110.1 . . ?
H62A C62 H62B 108.4 . . ?
C62 C63 C64 107.4(8) . . ?
C62 C63 H63A 110.2 . . ?
C64 C63 H63A 110.2 . . ?
C62 C63 H63B 110.2 . . ?
C64 C63 H63B 110.2 . . ?
H63A C63 H63B 108.5 . . ?
C63 C64 C65 107.0(7) . . ?
C63 C64 H64A 110.3 . . ?
C65 C64 H64A 110.3 . . ?
C63 C64 H64B 110.3 . . ?
C65 C64 H64B 110.3 . . ?
H64A C64 H64B 108.6 . . ?
O61 C65 C64 107.1(7) . . ?
O61 C65 H65A 110.3 . . ?
C64 C65 H65A 110.3 . . ?
O61 C65 H65B 110.3 . . ?
C64 C65 H65B 110.3 . . ?
H65A C65 H65B 108.6 . . ?
O66 C67 C68 105.4(3) . . ?
O66 C67 H67A 110.7 . . ?
C68 C67 H67A 110.7 . . ?
O66 C67 H67B 110.7 . . ?
C68 C67 H67B 110.7 . . ?
H67A C67 H67B 108.8 . . ?
C67 C68 C69 102.6(4) . . ?
C67 C68 H68A 111.3 . . ?
C69 C68 H68A 111.3 . . ?
C67 C68 H68B 111.3 . . ?
C69 C68 H68B 111.3 . . ?
H68A C68 H68B 109.2 . . ?
C70 C69 C68 103.5(3) . . ?
C70 C69 H69A 111.1 . . ?
C68 C69 H69A 111.1 . . ?
C70 C69 H69B 111.1 . . ?
C68 C69 H69B 111.1 . . ?
H69A C69 H69B 109.0 . . ?
O66 C70 C69 106.9(3) . . ?
O66 C70 H70A 110.3 . . ?
C69 C70 H70A 110.3 . . ?
O66 C70 H70B 110.3 . . ?
C69 C70 H70B 110.3 . . ?
H70A C70 H70B 108.6 . . ?
O1 B1 C30 126.5(2) . . ?
O1 B1 C2 117.9(2) . . ?
C30 B1 C2 115.6(2) . . ?
O23 B23 C24 123.6(3) . . ?
O23 B23 C22 120.4(3) . . ?
C24 B23 C22 116.0(2) . . ?
O27 B27 C28 119.9(2) . . ?
O27 B27 C26 124.5(2) . . ?
C28 B27 C26 115.5(2) . . ?
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
O1 B1 1.364(4) . ?
O1 H1 0.978(7) . ?
O23 B23 1.368(4) . ?
O23 H23 0.978(7) . ?
O27 B27 1.366(3) . ?
O27 H27 0.979(7) . ?
O61 C62 1.374(7) . ?
O61 C65 1.397(7) . ?
O66 C67 1.431(4) . ?
O66 C70 1.442(4) . ?
N8 C9 1.398(3) . ?
N8 C7 1.406(3) . ?
N8 C32 1.444(3) . ?
N12 C13 1.393(3) . ?
N12 C11 1.406(3) . ?
N12 C39 1.440(3) . ?
N16 C15 1.401(3) . ?
N16 C17 1.403(3) . ?
N16 C46 1.445(3) . ?
C2 C7 1.400(4) . ?
C2 C3 1.409(3) . ?
C2 B1 1.544(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(4) . ?
C4 C31 1.514(4) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(3) . ?
C6 H6 0.9500 . ?
C9 C10 1.395(3) . ?
C9 C30 1.421(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C28 1.416(3) . ?
C13 C14 1.396(3) . ?
C13 C26 1.418(3) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C24 1.415(3) . ?
C17 C18 1.400(4) . ?
C17 C22 1.408(4) . ?
C18 C19 1.375(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(4) . ?
C20 C53 1.515(4) . ?
C21 C22 1.414(4) . ?
C21 H21 0.9500 . ?
C22 B23 1.542(4) . ?
C24 C25 1.406(3) . ?
C24 B23 1.534(4) . ?
C25 C26 1.394(3) . ?
C25 H25 0.9500 . ?
C26 B27 1.555(4) . ?
C28 C29 1.400(3) . ?
C28 B27 1.542(4) . ?
C29 C30 1.401(3) . ?
C29 H29 0.9500 . ?
C30 B1 1.543(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C37 1.377(4) . ?
C32 C33 1.383(3) . ?
C33 C34 1.375(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(4) . ?
C35 C38 1.509(4) . ?
C36 C37 1.388(4) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.377(3) . ?
C39 C44 1.383(3) . ?
C40 C41 1.387(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.389(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.383(4) . ?
C42 C45 1.506(4) . ?
C43 C44 1.378(4) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 C47 1.377(4) . ?
C46 C51 1.388(3) . ?
C47 C48 1.388(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.388(4) . ?
C48 H48 0.9500 . ?
C49 C50 1.385(4) . ?
C49 C52 1.503(4) . ?
C50 C51 1.378(4) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C62 C63 1.404(11) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.416(14) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 C65 1.425(12) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C67 C68 1.479(6) . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
C68 C69 1.513(6) . ?
C68 H68A 0.9900 . ?
C68 H68B 0.9900 . ?
C69 C70 1.504(6) . ?
C69 H69A 0.9900 . ?
C69 H69B 0.9900 . ?
C70 H70A 0.9900 . ?
C70 H70B 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O61 . . . 2.747(3) 0.98(2) 1.79(2) 164(3) no
O27 H27 O66 . . . 2.914(3) 0.98(3) 1.96(3) 166(3) no
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
C7 C2 C3 C4 1.1(4) . . . . ?
B1 C2 C3 C4 -179.2(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 C31 178.0(3) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C31 C4 C5 C6 -179.1(3) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C3 C2 C7 N8 -179.9(2) . . . . ?
B1 C2 C7 N8 0.3(3) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
B1 C2 C7 C6 179.8(2) . . . . ?
C9 N8 C7 C2 1.2(3) . . . . ?
C32 N8 C7 C2 -171.6(2) . . . . ?
C9 N8 C7 C6 -178.3(2) . . . . ?
C32 N8 C7 C6 8.9(3) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C5 C6 C7 N8 178.9(2) . . . . ?
C7 N8 C9 C10 176.0(2) . . . . ?
C32 N8 C9 C10 -11.1(3) . . . . ?
C7 N8 C9 C30 -3.3(3) . . . . ?
C32 N8 C9 C30 169.5(2) . . . . ?
N8 C9 C10 C11 -179.4(2) . . . . ?
C30 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 N12 175.1(2) . . . . ?
C9 C10 C11 C28 -4.1(3) . . . . ?
C13 N12 C11 C10 176.9(2) . . . . ?
C39 N12 C11 C10 -3.9(3) . . . . ?
C13 N12 C11 C28 -3.9(3) . . . . ?
C39 N12 C11 C28 175.3(2) . . . . ?
C11 N12 C13 C14 175.9(2) . . . . ?
C39 N12 C13 C14 -3.3(3) . . . . ?
C11 N12 C13 C26 -3.4(3) . . . . ?
C39 N12 C13 C26 177.4(2) . . . . ?
N12 C13 C14 C15 176.9(2) . . . . ?
C26 C13 C14 C15 -3.7(3) . . . . ?
C13 C14 C15 N16 178.2(2) . . . . ?
C13 C14 C15 C24 -2.5(3) . . . . ?
C17 N16 C15 C14 173.6(2) . . . . ?
C46 N16 C15 C14 -11.2(3) . . . . ?
C17 N16 C15 C24 -5.8(3) . . . . ?
C46 N16 C15 C24 169.5(2) . . . . ?
C15 N16 C17 C18 -177.9(2) . . . . ?
C46 N16 C17 C18 7.0(3) . . . . ?
C15 N16 C17 C22 1.6(4) . . . . ?
C46 N16 C17 C22 -173.6(2) . . . . ?
N16 C17 C18 C19 178.9(3) . . . . ?
C22 C17 C18 C19 -0.6(4) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C18 C19 C20 C53 -179.3(3) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C53 C20 C21 C22 -179.7(3) . . . . ?
C18 C17 C22 C21 1.4(4) . . . . ?
N16 C17 C22 C21 -178.0(2) . . . . ?
C18 C17 C22 B23 -177.7(3) . . . . ?
N16 C17 C22 B23 2.9(4) . . . . ?
C20 C21 C22 C17 -1.4(4) . . . . ?
C20 C21 C22 B23 177.7(3) . . . . ?
C14 C15 C24 C25 5.7(3) . . . . ?
N16 C15 C24 C25 -175.0(2) . . . . ?
C14 C15 C24 B23 -174.2(2) . . . . ?
N16 C15 C24 B23 5.1(4) . . . . ?
C15 C24 C25 C26 -3.1(4) . . . . ?
B23 C24 C25 C26 176.8(2) . . . . ?
C24 C25 C26 C13 -2.6(3) . . . . ?
C24 C25 C26 B27 174.3(2) . . . . ?
N12 C13 C26 C25 -174.6(2) . . . . ?
C14 C13 C26 C25 6.1(3) . . . . ?
N12 C13 C26 B27 8.2(3) . . . . ?
C14 C13 C26 B27 -171.1(2) . . . . ?
C10 C11 C28 C29 4.7(3) . . . . ?
N12 C11 C28 C29 -174.5(2) . . . . ?
C10 C11 C28 B27 -175.3(2) . . . . ?
N12 C11 C28 B27 5.5(3) . . . . ?
C11 C28 C29 C30 -1.4(3) . . . . ?
B27 C28 C29 C30 178.6(2) . . . . ?
C28 C29 C30 C9 -2.5(3) . . . . ?
C28 C29 C30 B1 176.2(2) . . . . ?
C10 C9 C30 C29 3.2(3) . . . . ?
N8 C9 C30 C29 -177.5(2) . . . . ?
C10 C9 C30 B1 -175.6(2) . . . . ?
N8 C9 C30 B1 3.8(3) . . . . ?
C9 N8 C32 C37 90.2(3) . . . . ?
C7 N8 C32 C37 -96.7(3) . . . . ?
C9 N8 C32 C33 -85.0(3) . . . . ?
C7 N8 C32 C33 88.2(3) . . . . ?
C37 C32 C33 C34 -1.7(4) . . . . ?
N8 C32 C33 C34 173.5(2) . . . . ?
C32 C33 C34 C35 -1.0(4) . . . . ?
C33 C34 C35 C36 2.8(5) . . . . ?
C33 C34 C35 C38 -177.1(3) . . . . ?
C34 C35 C36 C37 -2.0(5) . . . . ?
C38 C35 C36 C37 177.8(3) . . . . ?
C33 C32 C37 C36 2.4(4) . . . . ?
N8 C32 C37 C36 -172.7(2) . . . . ?
C35 C36 C37 C32 -0.6(5) . . . . ?
C13 N12 C39 C40 -85.6(3) . . . . ?
C11 N12 C39 C40 95.2(3) . . . . ?
C13 N12 C39 C44 94.0(3) . . . . ?
C11 N12 C39 C44 -85.2(3) . . . . ?
C44 C39 C40 C41 -0.8(4) . . . . ?
N12 C39 C40 C41 178.8(2) . . . . ?
C39 C40 C41 C42 0.2(4) . . . . ?
C40 C41 C42 C43 0.4(5) . . . . ?
C40 C41 C42 C45 -179.3(3) . . . . ?
C41 C42 C43 C44 -0.3(4) . . . . ?
C45 C42 C43 C44 179.4(3) . . . . ?
C42 C43 C44 C39 -0.3(4) . . . . ?
C40 C39 C44 C43 0.9(4) . . . . ?
N12 C39 C44 C43 -178.7(2) . . . . ?
C15 N16 C46 C47 86.7(3) . . . . ?
C17 N16 C46 C47 -97.8(3) . . . . ?
C15 N16 C46 C51 -89.3(3) . . . . ?
C17 N16 C46 C51 86.2(3) . . . . ?
C51 C46 C47 C48 2.4(4) . . . . ?
N16 C46 C47 C48 -173.6(2) . . . . ?
C46 C47 C48 C49 -1.0(4) . . . . ?
C47 C48 C49 C50 -1.5(4) . . . . ?
C47 C48 C49 C52 178.5(3) . . . . ?
C48 C49 C50 C51 2.7(4) . . . . ?
C52 C49 C50 C51 -177.3(3) . . . . ?
C49 C50 C51 C46 -1.4(4) . . . . ?
C47 C46 C51 C50 -1.2(4) . . . . ?
N16 C46 C51 C50 174.9(2) . . . . ?
C65 O61 C62 C63 11.6(9) . . . . ?
O61 C62 C63 C64 -9.5(13) . . . . ?
C62 C63 C64 C65 3.8(14) . . . . ?
C62 O61 C65 C64 -9.1(9) . . . . ?
C63 C64 C65 O61 3.1(11) . . . . ?
C70 O66 C67 C68 26.9(4) . . . . ?
O66 C67 C68 C69 -36.5(4) . . . . ?
C67 C68 C69 C70 32.1(5) . . . . ?
C67 O66 C70 C69 -5.8(4) . . . . ?
C68 C69 C70 O66 -16.7(5) . . . . ?
C29 C30 B1 O1 -1.1(4) . . . . ?
C9 C30 B1 O1 177.5(3) . . . . ?
C29 C30 B1 C2 179.1(2) . . . . ?
C9 C30 B1 C2 -2.2(3) . . . . ?
C7 C2 B1 O1 -179.5(2) . . . . ?
C3 C2 B1 O1 0.7(4) . . . . ?
C7 C2 B1 C30 0.3(3) . . . . ?
C3 C2 B1 C30 -179.5(2) . . . . ?
C25 C24 B23 O23 0.2(5) . . . . ?
C15 C24 B23 O23 -179.9(3) . . . . ?
C25 C24 B23 C22 179.3(2) . . . . ?
C15 C24 B23 C22 -0.8(4) . . . . ?
C17 C22 B23 O23 176.0(3) . . . . ?
C21 C22 B23 O23 -3.1(5) . . . . ?
C17 C22 B23 C24 -3.1(4) . . . . ?
C21 C22 B23 C24 177.8(3) . . . . ?
C29 C28 B27 O27 1.0(4) . . . . ?
C11 C28 B27 O27 -179.0(2) . . . . ?
C29 C28 B27 C26 179.4(2) . . . . ?
C11 C28 B27 C26 -0.6(3) . . . . ?
C25 C26 B27 O27 -4.7(4) . . . . ?
C13 C26 B27 O27 172.2(2) . . . . ?
C25 C26 B27 C28 177.0(2) . . . . ?
C13 C26 B27 C28 -6.1(3) . . . . ?
