#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:30:09 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298158 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/34/1573435.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_1573435
loop_
_publ_author_name
'Liu, Le'
'Song, Shuangji'
'Lee, Jiyeon'
'Rao, Yutao'
'Xu, Ling'
'Zhou, Mingbo'
'Yin, Bangshao'
'Oh, Juwon'
'Kim, Jiwon'
'Osuka, Atsuhiro'
'Song, Jianxin'
_publ_section_title
;
 Sub-m-benziporphyrin: a subcarbaporphyrinoid and its
 BIII complex with an unprecedented planar tridentate
 14π-aromatic network.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1155
_journal_page_last               1160
_journal_paper_doi               10.1039/d4sc07199a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C49 H39 B N2'
_chemical_formula_sum            'C49 H39 B N2'
_chemical_formula_weight         666.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-08-25 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                103.399(7)
_cell_angle_beta                 109.908(8)
_cell_angle_gamma                94.935(7)
_cell_formula_units_Z            2
_cell_length_a                   11.6677(12)
_cell_length_b                   12.7694(11)
_cell_length_c                   14.5328(8)
_cell_measurement_reflns_used    2183
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      69.5590
_cell_measurement_theta_min      3.3460
_cell_volume                     1948.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -76.00   1.00    5.00    --  -34.73 -57.00 -30.00   26
  2  ω    -32.00  51.00   1.00    5.00    --   34.73 -38.00  60.00   83
  3  ω    -33.00  37.00   1.00    5.00    --   34.73 -38.00 150.00   70
  4  ω     17.00  44.00   1.00    5.00    --   34.73  38.00-120.00   27
  5  ω     36.00  88.00   1.00    5.00    --   34.73-125.00-180.00   52
  6  ω      8.00  97.00   1.00    5.00    --   34.73  77.00 -90.00   89
  7  ω     23.00 104.00   1.00    5.00    --   34.73  38.00  30.00   81
  8  ω     71.00 104.00   1.00    5.00    --   34.73  38.00-120.00   33
  9  ω     42.00  68.00   1.00    5.00    --   34.73 -99.00 -30.00   26
 10  ω     32.00  70.00   1.00    5.00    --   34.73 -99.00  30.00   38
 11  ω     38.00  80.00   1.00   20.00    --  105.88 -94.00 120.00   42
 12  ω     84.00 116.00   1.00   20.00    --  105.88-111.00 -60.00   32
 13  ω     98.00 172.00   1.00   20.00    --  105.88  61.00-180.00   74
 14  ω     56.00 124.00   1.00   20.00    --  105.88 -77.00-180.00   68
 15  ω     39.00 120.00   1.00   20.00    --  105.88 -45.00 120.00   81
 16  ω     65.00  99.00   1.00   20.00    --  105.88 178.00  90.00   34
 17  ω     42.00 104.00   1.00   20.00    --  105.88 -45.00-120.00   62
 18  ω    120.00 150.00   1.00   20.00    --  105.88 111.00  30.00   30
 19  ω     38.00 121.00   1.00   20.00    --  105.88 -45.00  30.00   83
 20  ω     39.00  66.00   1.00   20.00    --  105.88 -61.00  30.00   27
 21  ω    105.00 133.00   1.00   20.00    --  105.88 178.00  90.00   28
 22  ω     62.00 110.00   1.00   20.00    --  105.88-111.00-180.00   48
 23  ω     37.00 108.00   1.00   20.00    --  105.88 -94.00  30.00   71
 24  ω     40.00 174.00   1.00   20.00    --  105.88   0.00 -30.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1192533000
_diffrn_orient_matrix_UB_12      -0.0860683000
_diffrn_orient_matrix_UB_13      -0.0396515000
_diffrn_orient_matrix_UB_21      -0.0162247000
_diffrn_orient_matrix_UB_22      0.0402870000
_diffrn_orient_matrix_UB_23      0.1025068000
_diffrn_orient_matrix_UB_31      -0.0768004000
_diffrn_orient_matrix_UB_32      0.0828689000
_diffrn_orient_matrix_UB_33      -0.0412457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11838
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.368
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0815
_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)+(0.1341P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2160
_refine_ls_wR_factor_ref         0.2447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4447
_reflns_number_total             6887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc07199a2.cif
_cod_data_source_block           exp_3473_sq
_cod_depositor_comments
'Adding full bibliography for 1573430--1573435.cif.'
_cod_database_code               1573435
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C100 H100 N1 O1 B1'
_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_max   0.976
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H26A,H26B,H26C} of C26, {H28A,H28B,H28C} of C28
 At 1.5 times of:
  {H38A,H38B,H38C} of C38, {H39A,H39B,H39C} of C39, {H40A,H40B,H40C} of C40,
  {H47A,H47B,H47C} of C47, {H49A,H49B,H49C} of C49, {H48A,H48B,H48C} of C48
2. Others
 Fixed Sof: H26A(0.5) H26B(0.5) H26C(0.5) H28A(0.5) H28B(0.5) H28C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C26(H26B,H26C), C28(H28A,H28B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C21(H21), C22(H22), C26(H26A), C27(H27), C28(H28C),
 C34(H34), C36(H36), C42(H42), C44(H44)
3.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C47(H47A,H47B,
 H47C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.628
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3113(3) 0.3295(2) 0.2645(2) 0.0336(6) Uani 1 1 d . . . . .
C1 C 0.2519(5) 0.0320(3) -0.1157(3) 0.0518(10) Uani 1 1 d . . . . .
H1 H 0.166492 0.001561 -0.138504 0.062 Uiso 1 1 calc R . . . .
B1 B 0.2638(4) 0.4204(4) 0.2405(3) 0.0391(9) Uani 1 1 d . . . . .
N2 N 0.2882(3) 0.4519(2) 0.1630(2) 0.0339(6) Uani 1 1 d . . . . .
C2 C 0.3045(4) 0.1206(3) -0.0325(3) 0.0443(9) Uani 1 1 d . . . . .
H2 H 0.254057 0.152976 0.001223 0.053 Uiso 1 1 calc R . . . .
C3 C 0.4323(4) 0.1655(3) 0.0051(3) 0.0381(8) Uani 1 1 d . . . . .
C4 C 0.4889(3) 0.2565(3) 0.0910(3) 0.0349(8) Uani 1 1 d . . . . .
C5 C 0.6167(4) 0.2975(3) 0.1269(3) 0.0382(8) Uani 1 1 d . . . . .
C6 C 0.6787(4) 0.3909(3) 0.2127(3) 0.0454(9) Uani 1 1 d . . . . .
H6 H 0.632375 0.426783 0.248827 0.055 Uiso 1 1 calc R . . . .
C7 C 0.7999(4) 0.4290(4) 0.2436(3) 0.0512(10) Uani 1 1 d . . . . .
H7 H 0.837511 0.492201 0.299984 0.061 Uiso 1 1 calc R . . . .
C8 C 0.8727(4) 0.3764(4) 0.1933(4) 0.0552(11) Uani 1 1 d . . . . .
H8 H 0.958948 0.403870 0.216466 0.066 Uiso 1 1 calc R . . . .
C9 C 0.8199(4) 0.2870(4) 0.1124(3) 0.0530(11) Uani 1 1 d . . . . .
H9 H 0.870112 0.251591 0.080094 0.064 Uiso 1 1 calc R . . . .
C10 C 0.6911(4) 0.2451(3) 0.0749(3) 0.0428(9) Uani 1 1 d . . . . .
C11 C 0.6323(4) 0.1567(3) -0.0121(3) 0.0495(10) Uani 1 1 d . . . . .
H11 H 0.680495 0.123297 -0.047625 0.059 Uiso 1 1 calc R . . . .
C12 C 0.5082(4) 0.1165(3) -0.0478(3) 0.0435(9) Uani 1 1 d . . . . .
C13 C 0.4483(5) 0.0265(4) -0.1364(3) 0.0550(11) Uani 1 1 d . . . . .
H13 H 0.495716 -0.005123 -0.173554 0.066 Uiso 1 1 calc R . . . .
C14 C 0.3284(5) -0.0146(4) -0.1687(3) 0.0599(13) Uani 1 1 d . . . . .
H14 H 0.292361 -0.075552 -0.227478 0.072 Uiso 1 1 calc R . . . .
C15 C 0.2637(3) 0.5493(3) 0.1426(3) 0.0340(7) Uani 1 1 d . . . . .
C16 C 0.3164(3) 0.5579(3) 0.0682(3) 0.0362(8) Uani 1 1 d . . . . .
H16 H 0.313217 0.615568 0.036634 0.043 Uiso 1 1 calc R . . . .
C17 C 0.3729(3) 0.4679(3) 0.0498(3) 0.0354(7) Uani 1 1 d . . . . .
H17 H 0.413282 0.453097 0.002710 0.042 Uiso 1 1 calc R . . . .
C18 C 0.3599(3) 0.4011(3) 0.1139(3) 0.0338(7) Uani 1 1 d . . . . .
C19 C 0.4095(3) 0.3118(3) 0.1425(2) 0.0321(7) Uani 1 1 d . . . . .
C20 C 0.3904(3) 0.2790(3) 0.2229(3) 0.0352(7) Uani 1 1 d . . . . .
C21 C 0.4404(4) 0.2111(3) 0.2853(3) 0.0379(8) Uani 1 1 d . . . . .
H21 H 0.496835 0.164096 0.275919 0.045 Uiso 1 1 calc R . . . .
C22 C 0.3933(4) 0.2244(3) 0.3625(3) 0.0401(8) Uani 1 1 d . . . . .
H22 H 0.412389 0.188075 0.414532 0.048 Uiso 1 1 calc R . . . .
C23 C 0.3121(3) 0.3013(3) 0.3507(3) 0.0356(7) Uani 1 1 d . . . . .
C24 C 0.2502(3) 0.3606(3) 0.4087(3) 0.0341(7) Uani 1 1 d . . . . .
C25 C 0.2020(3) 0.4541(3) 0.3880(3) 0.0341(7) Uani 1 1 d . . . . .
C26 C 0.1495(4) 0.5247(3) 0.4534(3) 0.0459(9) Uani 1 1 d . . . . .
H26A H 0.137597 0.505516 0.509289 0.055 Uiso 0.5 1 calc R . P A -1
H26B H 0.074148 0.480730 0.451462 0.055 Uiso 0.5 1 calc R . P A -1
H26C H 0.210147 0.544955 0.524403 0.055 Uiso 0.5 1 calc R . P A -1
C27 C 0.1179(4) 0.6217(4) 0.4291(3) 0.0529(10) Uani 1 1 d . . . . .
H27 H 0.085539 0.667406 0.472153 0.064 Uiso 1 1 calc R . . . .
C28 C 0.1295(4) 0.6585(3) 0.3461(3) 0.0468(9) Uani 1 1 d . . . . .
H28A H 0.183423 0.731563 0.374420 0.056 Uiso 0.5 1 calc R . P B -1
H28B H 0.046641 0.667482 0.303079 0.056 Uiso 0.5 1 calc R . P B -1
H28C H 0.106026 0.725004 0.334174 0.056 Uiso 0.5 1 calc R . P B -1
C29 C 0.1805(3) 0.5863(3) 0.2802(3) 0.0343(7) Uani 1 1 d . . . . .
C30 C 0.2058(3) 0.4880(3) 0.3026(3) 0.0349(7) Uani 1 1 d . . . . .
C31 C 0.2076(3) 0.6164(3) 0.1999(3) 0.0342(7) Uani 1 1 d . . . . .
C32 C 0.1860(3) 0.7255(3) 0.1826(3) 0.0359(8) Uani 1 1 d . . . . .
C33 C 0.2796(3) 0.8174(3) 0.2331(3) 0.0407(8) Uani 1 1 d . . . . .
C34 C 0.2558(4) 0.9189(3) 0.2198(3) 0.0416(8) Uani 1 1 d . . . . .
H34 H 0.320121 0.981050 0.254459 0.050 Uiso 1 1 calc R . . . .
C35 C 0.1413(4) 0.9322(3) 0.1575(3) 0.0383(8) Uani 1 1 d . . . . .
C36 C 0.0504(4) 0.8410(3) 0.1067(3) 0.0438(9) Uani 1 1 d . . . . .
H36 H -0.028132 0.848424 0.062627 0.053 Uiso 1 1 calc R . . . .
C37 C 0.0698(4) 0.7370(3) 0.1179(3) 0.0418(8) Uani 1 1 d . . . . .
C38 C -0.0329(4) 0.6406(3) 0.0605(4) 0.0569(11) Uani 1 1 d . . . . .
H38A H -0.014316 0.594434 0.005257 0.085 Uiso 1 1 calc GR . . . .
H38B H -0.110737 0.666083 0.031829 0.085 Uiso 1 1 calc GR . . . .
H38C H -0.040976 0.598061 0.106823 0.085 Uiso 1 1 calc GR . . . .
C39 C 0.4066(4) 0.8080(4) 0.3028(4) 0.0660(13) Uani 1 1 d . . . . .
H39A H 0.397415 0.768270 0.350786 0.099 Uiso 1 1 calc GR . . . .
H39B H 0.455386 0.881319 0.340670 0.099 Uiso 1 1 calc GR . . . .
H39C H 0.449092 0.768165 0.261921 0.099 Uiso 1 1 calc GR . . . .
C40 C 0.1187(4) 1.0443(3) 0.1444(3) 0.0498(10) Uani 1 1 d . . . . .
H40A H 0.128449 1.093849 0.210230 0.075 Uiso 1 1 calc GR . . . .
H40B H 0.034429 1.037718 0.095540 0.075 Uiso 1 1 calc GR . . . .
H40C H 0.178618 1.073712 0.119045 0.075 Uiso 1 1 calc GR . . . .
C41 C 0.1383(4) 0.2630(3) 0.4918(3) 0.0403(8) Uani 1 1 d . . . . .
C42 C 0.1329(4) 0.2366(3) 0.5791(3) 0.0473(9) Uani 1 1 d . . . . .
H42 H 0.060148 0.192309 0.574131 0.057 Uiso 1 1 calc R . . . .
C43 C 0.2311(4) 0.2738(3) 0.6723(3) 0.0461(9) Uani 1 1 d . . . . .
C44 C 0.3371(4) 0.3364(3) 0.6777(3) 0.0421(8) Uani 1 1 d . . . . .
H44 H 0.405603 0.360845 0.740794 0.050 Uiso 1 1 calc R . . . .
C45 C 0.3464(4) 0.3647(3) 0.5931(3) 0.0393(8) Uani 1 1 d . . . . .
C46 C 0.2448(3) 0.3271(3) 0.4998(2) 0.0336(7) Uani 1 1 d . . . . .
C47 C 0.4610(4) 0.4354(4) 0.6029(3) 0.0509(10) Uani 1 1 d . . . . .
H47A H 0.441166 0.504981 0.590064 0.076 Uiso 1 1 calc GR . . . .
H47B H 0.494205 0.398218 0.553197 0.076 Uiso 1 1 calc GR . . . .
H47C H 0.522994 0.449503 0.671888 0.076 Uiso 1 1 calc GR . . . .
C48 C 0.2226(5) 0.2474(5) 0.7660(4) 0.0650(13) Uani 1 1 d . . . . .
H48A H 0.219624 0.314297 0.813872 0.097 Uiso 1 1 calc GR . . . .
H48B H 0.295324 0.217197 0.798609 0.097 Uiso 1 1 calc GR . . . .
H48C H 0.147304 0.193584 0.746470 0.097 Uiso 1 1 calc GR . . . .
C49 C 0.0286(4) 0.2233(4) 0.3924(3) 0.0533(10) Uani 1 1 d . . . . .
H49A H -0.034845 0.174159 0.399901 0.080 Uiso 1 1 calc GR . . . .
H49B H 0.055112 0.183876 0.339012 0.080 Uiso 1 1 calc GR . . . .
H49C H -0.005801 0.286098 0.373648 0.080 Uiso 1 1 calc GR . . . .
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'
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
C20 N1 B1 123.3(3) . . ?
C23 N1 B1 121.6(3) . . ?
C23 N1 C20 112.9(3) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C14 118.8(4) . . ?
C14 C1 H1 120.6 . . ?
N1 B1 C30 121.9(3) . . ?
N2 B1 N1 116.1(3) . . ?
N2 B1 C30 121.5(3) . . ?
B1 N2 C18 123.4(3) . . ?
C15 N2 B1 121.8(3) . . ?
C15 N2 C18 113.6(3) . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.8(4) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C12 118.7(3) . . ?
C4 C3 C2 123.0(3) . . ?
C4 C3 C12 118.4(4) . . ?
C3 C4 C19 118.7(3) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 C19 120.1(3) . . ?
C4 C5 C6 123.5(3) . . ?
C4 C5 C10 119.5(3) . . ?
C6 C5 C10 117.0(4) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.0(4) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.3(4) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 118.8(4) . . ?
C11 C10 C5 118.4(4) . . ?
C11 C10 C9 122.8(4) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 C10 122.5(3) . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C3 120.0(4) . . ?
C11 C12 C13 122.5(4) . . ?
C13 C12 C3 117.5(4) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 H13 118.9 . . ?
C1 C14 H14 119.5 . . ?
C13 C14 C1 120.9(4) . . ?
C13 C14 H14 119.5 . . ?
N2 C15 C16 104.6(3) . . ?
N2 C15 C31 118.6(3) . . ?
C31 C15 C16 136.6(3) . . ?
C15 C16 H16 125.7 . . ?
C17 C16 C15 108.7(3) . . ?
C17 C16 H16 125.7 . . ?
C16 C17 H17 125.7 . . ?
C16 C17 C18 108.7(3) . . ?
C18 C17 H17 125.7 . . ?
N2 C18 C17 104.2(3) . . ?
N2 C18 C19 118.8(3) . . ?
C19 C18 C17 136.6(3) . . ?
C18 C19 C4 119.6(3) . . ?
C18 C19 C20 119.8(3) . . ?
C20 C19 C4 120.5(3) . . ?
N1 C20 C19 118.1(3) . . ?
N1 C20 C21 104.6(3) . . ?
C19 C20 C21 137.0(3) . . ?
C20 C21 H21 125.6 . . ?
C22 C21 C20 108.8(3) . . ?
C22 C21 H21 125.6 . . ?
C21 C22 H22 125.6 . . ?
C21 C22 C23 108.8(3) . . ?
C23 C22 H22 125.6 . . ?
N1 C23 C22 104.8(3) . . ?
N1 C23 C24 117.7(3) . . ?
C24 C23 C22 137.0(3) . . ?
C23 C24 C46 118.3(3) . . ?
C25 C24 C23 122.3(3) . . ?
C25 C24 C46 119.2(3) . . ?
C24 C25 C26 123.7(3) . . ?
C24 C25 C30 120.7(3) . . ?
C30 C25 C26 115.6(3) . . ?
C25 C26 H26A 121.5 . . ?
C25 C26 H26B 108.0 . . ?
C25 C26 H26C 108.0 . . ?
H26A C26 C25 121.5 . . ?
H26A C26 H26A 0.0 . . ?
H26A C26 H26B 53.6 . . ?
H26A C26 H26B 53.6 . . ?
H26A C26 H26C 53.6 . . ?
H26A C26 H26C 53.6 . . ?
H26A C26 C27 121.5 . . ?
H26B C26 H26C 107.3 . . ?
C27 C26 C25 117.1(3) . . ?
C27 C26 H26A 121.5 . . ?
C27 C26 H26B 108.0 . . ?
C27 C26 H26C 108.0 . . ?
C26 C27 H27 116.7 . . ?
C26 C27 C28 126.6(4) . . ?
C28 C27 H27 116.7 . . ?
C27 C28 H28A 108.3 . . ?
C27 C28 H28B 108.3 . . ?
C27 C28 H28C 122.1 . . ?
C27 C28 C29 115.9(3) . . ?
H28A C28 C27 108.3 . . ?
H28A C28 H28A 0.0 . . ?
H28A C28 H28B 107.4 . . ?
H28A C28 H28B 107.4 . . ?
H28A C28 H28B 107.4 . . ?
H28A C28 H28C 53.7 . . ?
H28A C28 H28C 53.7 . . ?
H28A C28 C29 108.3 . . ?
H28B C28 C27 108.3 . . ?
H28B C28 H28A 107.4 . . ?
H28B C28 H28B 0.0 . . ?
H28B C28 H28C 53.7 . . ?
H28B C28 H28C 53.7 . . ?
H28B C28 C29 108.3 . . ?
C29 C28 H28A 108.3 . . ?
C29 C28 H28B 108.3 . . ?
C29 C28 H28C 122.1 . . ?
C30 C29 C28 116.6(3) . . ?
C30 C29 C31 121.0(3) . . ?
C31 C29 C28 122.4(3) . . ?
C25 C30 B1 115.4(3) . . ?
C29 C30 B1 115.9(3) . . ?
C29 C30 C25 127.8(3) . . ?
C15 C31 C29 121.1(3) . . ?
C15 C31 C32 119.5(3) . . ?
C29 C31 C32 119.2(3) . . ?
C33 C32 C31 120.4(3) . . ?
C33 C32 C37 119.2(3) . . ?
C37 C32 C31 120.3(3) . . ?
C32 C33 C39 120.7(3) . . ?
C34 C33 C32 119.5(3) . . ?
C34 C33 C39 119.8(4) . . ?
C33 C34 H34 118.9 . . ?
C35 C34 C33 122.1(4) . . ?
C35 C34 H34 118.9 . . ?
C34 C35 C40 120.7(4) . . ?
C36 C35 C34 117.9(3) . . ?
C36 C35 C40 121.3(3) . . ?
C35 C36 H36 119.0 . . ?
C35 C36 C37 122.0(4) . . ?
C37 C36 H36 119.0 . . ?
C32 C37 C38 121.3(3) . . ?
C36 C37 C32 119.2(4) . . ?
C36 C37 C38 119.5(4) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C33 C39 H39A 109.5 . . ?
C33 C39 H39B 109.5 . . ?
C33 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C35 C40 H40A 109.5 . . ?
C35 C40 H40B 109.5 . . ?
C35 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C49 120.1(4) . . ?
C46 C41 C42 118.7(4) . . ?
C46 C41 C49 121.2(3) . . ?
C41 C42 H42 119.2 . . ?
C43 C42 C41 121.6(4) . . ?
C43 C42 H42 119.2 . . ?
C42 C43 C48 121.0(4) . . ?
C44 C43 C42 118.4(3) . . ?
C44 C43 C48 120.6(4) . . ?
C43 C44 H44 119.1 . . ?
C43 C44 C45 121.9(4) . . ?
C45 C44 H44 119.1 . . ?
C44 C45 C46 118.6(4) . . ?
C44 C45 C47 120.2(4) . . ?
C46 C45 C47 121.2(3) . . ?
C41 C46 C24 119.5(3) . . ?
C41 C46 C45 120.8(3) . . ?
C45 C46 C24 119.7(3) . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C43 C48 H48A 109.5 . . ?
C43 C48 H48B 109.5 . . ?
C43 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C41 C49 H49A 109.5 . . ?
C41 C49 H49B 109.5 . . ?
C41 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
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
N1 B1 1.395(5) . ?
N1 C20 1.391(4) . ?
N1 C23 1.379(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.364(6) . ?
C1 C14 1.446(6) . ?
B1 N2 1.385(5) . ?
B1 C30 1.474(5) . ?
N2 C15 1.376(4) . ?
N2 C18 1.385(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.415(6) . ?
C3 C4 1.407(5) . ?
C3 C12 1.450(5) . ?
C4 C5 1.406(5) . ?
C4 C19 1.502(4) . ?
C5 C6 1.432(6) . ?
C5 C10 1.444(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.336(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.415(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.352(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.418(6) . ?
C10 C11 1.399(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.366(6) . ?
C12 C13 1.425(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.329(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.434(5) . ?
C15 C31 1.411(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.435(5) . ?
C18 C19 1.406(5) . ?
C19 C20 1.406(5) . ?
C20 C21 1.417(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.392(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.421(5) . ?
C23 C24 1.420(5) . ?
C24 C25 1.414(5) . ?
C24 C46 1.501(4) . ?
C25 C26 1.479(5) . ?
C25 C30 1.418(5) . ?
C26 H26A 0.9500 . ?
C26 H26A 0.9500 . ?
C26 H26B 0.9900 . ?
C26 H26C 0.9900 . ?
C26 C27 1.410(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.435(6) . ?
C28 H28A 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 H28B 0.9900 . ?
C28 H28C 0.9500 . ?
C28 C29 1.482(5) . ?
C29 C30 1.400(5) . ?
C29 C31 1.430(5) . ?
C31 C32 1.499(5) . ?
C32 C33 1.394(5) . ?
C32 C37 1.405(5) . ?
C33 C34 1.391(5) . ?
C33 C39 1.517(6) . ?
C34 H34 0.9500 . ?
C34 C35 1.385(5) . ?
C35 C36 1.372(6) . ?
C35 C40 1.521(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.402(5) . ?
C37 C38 1.496(6) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.405(5) . ?
C41 C46 1.383(5) . ?
C41 C49 1.508(6) . ?
C42 H42 0.9500 . ?
C42 C43 1.388(6) . ?
C43 C44 1.382(6) . ?
C43 C48 1.509(5) . ?
C44 H44 0.9500 . ?
C44 C45 1.393(5) . ?
C45 C46 1.407(5) . ?
C45 C47 1.493(6) . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
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
N1 B1 N2 C15 -169.7(3) . . . . ?
N1 B1 N2 C18 -2.9(6) . . . . ?
N1 B1 C30 C25 0.1(6) . . . . ?
N1 B1 C30 C29 170.0(4) . . . . ?
N1 C20 C21 C22 -1.4(4) . . . . ?
N1 C23 C24 C25 -7.7(6) . . . . ?
N1 C23 C24 C46 177.0(3) . . . . ?
C1 C2 C3 C4 -179.7(3) . . . . ?
C1 C2 C3 C12 0.9(5) . . . . ?
B1 N1 C20 C19 -9.0(5) . . . . ?
B1 N1 C20 C21 165.5(4) . . . . ?
B1 N1 C23 C22 -165.8(4) . . . . ?
B1 N1 C23 C24 6.9(6) . . . . ?
B1 N2 C15 C16 172.5(3) . . . . ?
B1 N2 C15 C31 -2.6(5) . . . . ?
B1 N2 C18 C17 -173.1(4) . . . . ?
B1 N2 C18 C19 1.0(5) . . . . ?
N2 B1 C30 C25 -171.5(4) . . . . ?
N2 B1 C30 C29 -1.6(6) . . . . ?
N2 C15 C16 C17 -1.8(4) . . . . ?
N2 C15 C31 C29 2.2(5) . . . . ?
N2 C15 C31 C32 176.9(3) . . . . ?
N2 C18 C19 C4 -179.2(3) . . . . ?
N2 C18 C19 C20 -2.8(5) . . . . ?
C2 C1 C14 C13 1.1(6) . . . . ?
C2 C3 C4 C5 178.9(3) . . . . ?
C2 C3 C4 C19 -3.0(5) . . . . ?
C2 C3 C12 C11 -178.6(3) . . . . ?
C2 C3 C12 C13 1.2(5) . . . . ?
C3 C4 C5 C6 178.8(3) . . . . ?
C3 C4 C5 C10 -0.2(5) . . . . ?
C3 C4 C19 C18 -92.5(4) . . . . ?
C3 C4 C19 C20 91.1(4) . . . . ?
C3 C12 C13 C14 -2.3(6) . . . . ?
C4 C3 C12 C11 1.9(5) . . . . ?
C4 C3 C12 C13 -178.2(3) . . . . ?
C4 C5 C6 C7 -178.6(4) . . . . ?
C4 C5 C10 C9 -179.6(3) . . . . ?
C4 C5 C10 C11 1.9(5) . . . . ?
C4 C19 C20 N1 -177.0(3) . . . . ?
C4 C19 C20 C21 10.8(7) . . . . ?
C5 C4 C19 C18 85.6(4) . . . . ?
C5 C4 C19 C20 -90.8(4) . . . . ?
C5 C6 C7 C8 -1.4(6) . . . . ?
C5 C10 C11 C12 -1.7(5) . . . . ?
C6 C5 C10 C9 1.3(5) . . . . ?
C6 C5 C10 C11 -177.1(3) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C10 1.2(6) . . . . ?
C8 C9 C10 C5 -2.1(5) . . . . ?
C8 C9 C10 C11 176.3(4) . . . . ?
C9 C10 C11 C12 179.9(4) . . . . ?
C10 C5 C6 C7 0.4(5) . . . . ?
C10 C11 C12 C3 -0.2(6) . . . . ?
C10 C11 C12 C13 179.9(4) . . . . ?
C11 C12 C13 C14 177.6(4) . . . . ?
C12 C3 C4 C5 -1.7(5) . . . . ?
C12 C3 C4 C19 176.4(3) . . . . ?
C12 C13 C14 C1 1.1(7) . . . . ?
C14 C1 C2 C3 -2.0(6) . . . . ?
C15 N2 C18 C17 -5.3(4) . . . . ?
C15 N2 C18 C19 168.8(3) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C15 C31 C32 C33 -85.3(4) . . . . ?
C15 C31 C32 C37 96.9(4) . . . . ?
C16 C15 C31 C29 -170.8(4) . . . . ?
C16 C15 C31 C32 3.8(7) . . . . ?
C16 C17 C18 N2 3.8(4) . . . . ?
C16 C17 C18 C19 -168.5(4) . . . . ?
C17 C18 C19 C4 -7.7(6) . . . . ?
C17 C18 C19 C20 168.7(4) . . . . ?
C18 N2 C15 C16 4.5(4) . . . . ?
C18 N2 C15 C31 -170.6(3) . . . . ?
C18 C19 C20 N1 6.7(5) . . . . ?
C18 C19 C20 C21 -165.6(4) . . . . ?
C19 C4 C5 C6 0.7(5) . . . . ?
C19 C4 C5 C10 -178.3(3) . . . . ?
C19 C20 C21 C22 171.5(4) . . . . ?
C20 N1 B1 N2 7.1(6) . . . . ?
C20 N1 B1 C30 -165.0(4) . . . . ?
C20 N1 C23 C22 -2.4(4) . . . . ?
C20 N1 C23 C24 170.3(3) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C22 C23 N1 1.4(4) . . . . ?
C21 C22 C23 C24 -169.2(4) . . . . ?
C22 C23 C24 C25 161.9(4) . . . . ?
C22 C23 C24 C46 -13.3(7) . . . . ?
C23 N1 B1 N2 168.7(3) . . . . ?
C23 N1 B1 C30 -3.3(6) . . . . ?
C23 N1 C20 C19 -172.1(3) . . . . ?
C23 N1 C20 C21 2.4(4) . . . . ?
C23 C24 C25 C26 -173.0(4) . . . . ?
C23 C24 C25 C30 4.7(6) . . . . ?
C23 C24 C46 C41 -99.9(4) . . . . ?
C23 C24 C46 C45 82.3(4) . . . . ?
C24 C25 C26 H26A -6.9 . . . . ?
C24 C25 C26 C27 173.1(4) . . . . ?
C24 C25 C30 B1 -0.8(5) . . . . ?
C24 C25 C30 C29 -169.3(4) . . . . ?
C25 C24 C46 C41 84.7(4) . . . . ?
C25 C24 C46 C45 -93.0(4) . . . . ?
C25 C26 C27 C28 1.1(7) . . . . ?
C26 C25 C30 B1 177.2(4) . . . . ?
C26 C25 C30 C29 8.7(6) . . . . ?
C26 C27 C28 H28A -122.1 . . . . ?
C26 C27 C28 H28B 121.7 . . . . ?
C26 C27 C28 C29 -0.2(7) . . . . ?
H26A C26 C27 C28 -178.9 . . . . ?
C27 C28 C29 C30 3.1(6) . . . . ?
C27 C28 C29 C31 -174.5(4) . . . . ?
C28 C29 C30 B1 -176.3(4) . . . . ?
C28 C29 C30 C25 -7.8(6) . . . . ?
C28 C29 C31 C15 175.8(4) . . . . ?
C28 C29 C31 C32 1.1(5) . . . . ?
H28A C28 C29 C30 125.0 . . . . ?
H28A C28 C29 C31 -52.6 . . . . ?
H28B C28 C29 C30 -118.8 . . . . ?
H28B C28 C29 C31 63.6 . . . . ?
C29 C31 C32 C33 89.5(4) . . . . ?
C29 C31 C32 C37 -88.3(4) . . . . ?
C30 B1 N2 C15 2.3(6) . . . . ?
C30 B1 N2 C18 169.2(4) . . . . ?
C30 C25 C26 H26A 175.3 . . . . ?
C30 C25 C26 C27 -4.7(6) . . . . ?
C30 C29 C31 C15 -1.7(6) . . . . ?
C30 C29 C31 C32 -176.4(3) . . . . ?
C31 C15 C16 C17 171.9(4) . . . . ?
C31 C29 C30 B1 1.3(5) . . . . ?
C31 C29 C30 C25 169.8(4) . . . . ?
C31 C32 C33 C34 -176.9(3) . . . . ?
C31 C32 C33 C39 2.7(6) . . . . ?
C31 C32 C37 C36 177.1(3) . . . . ?
C31 C32 C37 C38 -3.3(5) . . . . ?
C32 C33 C34 C35 0.0(6) . . . . ?
C33 C32 C37 C36 -0.8(5) . . . . ?
C33 C32 C37 C38 178.8(4) . . . . ?
C33 C34 C35 C36 -1.2(5) . . . . ?
C33 C34 C35 C40 -179.7(3) . . . . ?
C34 C35 C36 C37 1.3(6) . . . . ?
C35 C36 C37 C32 -0.4(6) . . . . ?
C35 C36 C37 C38 180.0(4) . . . . ?
C37 C32 C33 C34 0.9(5) . . . . ?
C37 C32 C33 C39 -179.4(4) . . . . ?
C39 C33 C34 C35 -179.6(4) . . . . ?
C40 C35 C36 C37 179.9(4) . . . . ?
C41 C42 C43 C44 -1.3(6) . . . . ?
C41 C42 C43 C48 178.3(4) . . . . ?
C42 C41 C46 C24 -177.1(3) . . . . ?
C42 C41 C46 C45 0.6(5) . . . . ?
C42 C43 C44 C45 1.4(5) . . . . ?
C43 C44 C45 C46 -0.6(5) . . . . ?
C43 C44 C45 C47 178.0(3) . . . . ?
C44 C45 C46 C24 177.3(3) . . . . ?
C44 C45 C46 C41 -0.4(5) . . . . ?
C46 C24 C25 C26 2.2(6) . . . . ?
C46 C24 C25 C30 179.9(3) . . . . ?
C46 C41 C42 C43 0.3(5) . . . . ?
C47 C45 C46 C24 -1.4(5) . . . . ?
C47 C45 C46 C41 -179.0(3) . . . . ?
C48 C43 C44 C45 -178.2(4) . . . . ?
C49 C41 C42 C43 -178.6(4) . . . . ?
C49 C41 C46 C24 1.7(5) . . . . ?
C49 C41 C46 C45 179.4(3) . . . . ?
