# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-CF3
_database_code_depnum_ccdc_archive 'CCDC 2394196'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.4y (K.Radacki, 2005-23)'
_audit_creation_date             2024-05-06
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C20 H14 B F3 N2'
_chemical_formula_sum            'C20 H14 B F3 N2'
_chemical_formula_weight         350.14
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   24.46310(10)
_cell_length_b                   9.34580(10)
_cell_length_c                   15.17920(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.1650(10)
_cell_angle_gamma                90
_cell_volume                     3333.17(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    44006
_cell_measurement_theta_min      3.7570
_cell_measurement_theta_max      74.9950

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
16 0 -3 0.1126
0 6 0 0.0553
-15 -1 -1 0.0140
15 1 0 0.0683
10 1 -9 0.1511
0 0 9 0.2832
5 -6 -1 0.0619
3 -6 0 0.0689
-16 -1 1 0.0216

_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.933
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     15.00  43.00   0.50    0.44    --    2.00  64.00 168.03   56
  2  ω   -128.00 -94.00   0.50    0.44    --  -79.50 -41.00 129.37   68
  3  ω     28.00  54.00   0.50    0.44    --   14.00  61.00  12.47   52
  4  ω   -128.00 -94.00   0.50    0.44    --  -79.50 -42.00 151.58   68
  5  ω     62.00  92.00   0.50    0.44    --   46.00  52.00  19.44   60
  6  ω   -123.00 -88.00   0.50    0.44    --  -74.00 -36.00 -88.30   70
  7  ω   -128.00 -94.00   0.50    0.44    --  -79.50 -41.00  89.63   68
  8  ω     54.00  84.00   0.50    0.44    --   38.00  52.00  70.03   60
  9  ω     28.00  54.00   0.50    0.44    --   14.00  61.00  71.09   52
 10  ω   -128.00 -94.00   0.50    0.44    --  -79.50 -41.00  76.97   68
 11  ω   -119.00 -84.00   0.50    0.44    --  -70.00 -40.00  90.28   70
 12  ω     58.00  89.00   0.50    0.44    --   42.00  51.00-104.14   62
 13  ω   -128.00 -94.00   0.50    0.44    --  -79.50 -42.00 -56.13   68
 14  ω   -105.00 -74.00   0.50    0.44    --  -58.00 -49.00  23.43   62
 15  ω   -110.00 -77.00   0.50    0.44    --  -62.00 -44.00  48.57   66
 16  ω   -114.00 -82.00   0.50    0.44    --  -66.00 -46.00 126.26   64
 17  ω     54.00  85.00   0.50    0.44    --   38.00  51.00-137.81   62
 18  ω    -97.00 -36.00   0.50    0.44    --  -79.50 115.00-106.33  122
 19  ω    -97.00 -36.00   0.50    0.44    --  -79.50 114.00  13.44  122
 20  ω    -33.00  -4.00   0.50    0.44    --  -18.00 110.00  -8.30   58
 21  ω   -120.00 -89.00   0.50    0.44    --  -74.00 -54.00 -26.14   62
 22  ω   -123.00 -93.00   0.50    0.44    --  -79.50 -61.00  76.59   60
 23  ω   -125.00 -90.00   0.50    0.44    --  -79.50-126.00 -42.98   70
 24  ω    -97.00 -36.00   0.50    0.44    --  -79.50 114.00 -32.47  122
 25  ω    -92.00 -33.00   0.50    0.44    --  -76.32 112.00   0.00  118
 26  ω   -120.00 -89.00   0.50    0.44    --  -74.00 -53.00  16.93   62
 27  ω    -98.00 -34.00   0.50    0.44    --  -79.50 120.00 101.44  128
 28  ω   -120.00 -89.00   0.50    0.44    --  -74.00 -54.00-157.50   62
 29  ω   -116.00 -85.00   0.50    0.44    --  -70.00 -52.00 -59.95   62
 30  ω    -92.00 -33.00   0.50    0.44    --  -76.32 112.00 -30.00  118
 31  ω   -106.00 -35.00   0.50    0.44    --  -79.50 136.00 -97.15  142
 32  ω    -97.00 -35.00   0.50    0.44    --  -79.50 116.00-117.74  124
 33  ω   -128.00 -93.00   0.50    0.44    --  -79.50 -39.00-149.03   70
 34  ω    -97.00 -36.00   0.50    0.44    --  -79.50 115.00 -73.57  122
 35  ω   -105.00 -74.00   0.50    0.44    --  -58.00 -47.00 -46.30   62
 36  ω    -92.00 -33.00   0.50    0.44    --  -76.32 112.00 150.00  118
 37  ω    -54.00 -28.00   0.50    0.44    --  -14.00 -58.00 170.23   52
 38  ω     19.00  66.00   0.50    0.44    --   60.18 -95.00-150.00   94
 39  ω   -125.00 -90.00   0.50    0.44    --  -79.50-126.00 166.35   70
 40  ω   -125.00 -90.00   0.50    0.44    --  -79.50-126.00 -65.43   70
 41  ω     40.00  86.00   0.50    0.44    --   80.28 -95.00  60.00   92
 42  ω   -128.00 -67.00   0.50    0.44    --  -79.50 -18.00  -9.47  122
 43  ω    -97.00 -36.00   0.50    0.44    --  -79.50 115.00  93.89  122
 44  ω     62.00  92.00   0.50    0.44    --   46.00  52.00 -87.64   60
 45  ω   -105.00 -74.00   0.50    0.44    --  -58.00 -49.00 147.87   62
 46  ω     32.00  60.00   0.50    0.44    --   18.00  59.00 -28.42   56
 47  ω     50.00  81.00   0.50    0.44    --   34.00  51.00 112.76   62
 48  ω   -125.00 -90.00   0.50    0.44    --  -79.50-126.00  35.38   70
 49  ω     19.00  66.00   0.50    0.44    --   60.18 -95.00 120.00   94
 50  ω   -125.00 -90.00   0.50    0.44    --  -79.50-126.00  55.02   70
 51  ω    -97.00 -36.00   0.50    0.44    --  -79.50 114.00-155.99  122
 52  ω   -125.00 -90.00   0.50    0.44    --  -79.50-126.00-115.20   70
 53  ω     40.00  86.00   0.50    0.44    --   80.28 -95.00   0.00   92
 54  ω   -125.00 -94.00   0.50    0.44    --  -79.50 -53.00 -81.38   62
 55  ω    -97.00 -36.00   0.50    0.44    --  -79.50 114.00  59.78  122
 56  ω     42.00  91.00   0.50    0.44    --   83.50 -99.00 -69.04   98
 57  ω     41.00  92.00   0.50    0.44    --   83.50-104.00 166.17  102
 58  ω   -119.00 -83.00   0.50    0.44    --  -70.00 -35.00 154.90   72
 59  ω    -98.00 -34.00   0.50    0.44    --  -79.50 120.00 165.30  128
 60  ω     42.00  73.00   0.50    0.44    --   26.00  51.00-166.65   62
 61  ω   -122.00 -89.00   0.50    0.44    --  -74.00 -42.00-114.28   66
 62  ω    -97.00 -36.00   0.50    0.44    --  -79.50 115.00 136.30  122
 63  ω   -126.00 -96.00   0.50    0.44    --  -79.50 -49.00   2.08   60
 64  ω   -123.00 -93.00   0.50    0.44    --  -79.50 -62.00  63.96   60
 65  ω   -118.00 -88.00   0.50    0.44    --  -74.00 -61.00-111.49   60
 66  ω    -97.00 -36.00   0.50    0.44    --  -79.50 114.00  67.49  122
 67  ω   -119.00 -88.00   0.50    0.44    --  -74.00 -57.00  -4.45   62
 68  ω   -124.00 -91.00   0.50    0.44    --  -79.50-124.00  78.58   66
 69  ω   -124.00 -91.00   0.50    0.44    --  -79.50-124.00 111.22   66
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0102689000
_diffrn_orient_matrix_UB_12      0.1618529000
_diffrn_orient_matrix_UB_13      -0.0156718000
_diffrn_orient_matrix_UB_21      0.0205533000
_diffrn_orient_matrix_UB_22      0.0253883000
_diffrn_orient_matrix_UB_23      0.1042949000
_diffrn_orient_matrix_UB_31      0.0614166000
_diffrn_orient_matrix_UB_32      0.0186345000
_diffrn_orient_matrix_UB_33      -0.0060771000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            76152
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.763
_diffrn_reflns_theta_max         75.142
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6654
_reflns_number_gt                6206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       
;
 CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))
;
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          
;
 One CF3 group is disordered., The displacement parameters of atoms C1_8 and 
 C1_81 were constrained to the same value with EADP keyword. The atomic 
 displacement parameters of atoms C1_8 to F3_81 were restraint with RIGU 
 keyword (esd = 0.016) in ShelXL input ('enhanced rigid bond' restraint for 
 all bonds in the connectivity list). The displacement parameters of atoms 
 C1_8 to F3_81 were restrained to the same value with similarity restraint 
 SIMU with esd = 0.032. The Uii displacement parameters of atoms C1_8 to 
 F3_81 were restrained with ISOR keyword (esd 0 0.008) to approximate 
 isotropic behavior. The distances between atoms C4_7 to C1_8 and C4_7 to 
 C1_81 were restrained during refinement to the same value using SADI.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0461P)²+1.2531P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6654
_refine_ls_number_parameters     500
_refine_ls_number_restraints     193
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.039
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_1 N 0.55694(4) 0.69012(10) 1.09276(6) 0.01980(19) Uani 1 1 d . . . . .
C1_1 C 0.47529(5) 0.81816(12) 1.07798(8) 0.0234(2) Uani 1 1 d . . . . .
H1_1 H 0.448373 0.858987 1.105260 0.028 Uiso 1 1 calc R U . . .
B1_1 B 0.55356(5) 0.69338(13) 0.99746(8) 0.0199(2) Uani 1 1 d . . . . .
N2_1 N 0.51716(4) 0.74918(10) 1.13206(6) 0.0229(2) Uani 1 1 d . . . . .
C2_1 C 0.46505(4) 0.83978(12) 0.98072(8) 0.0216(2) Uani 1 1 d . . . . .
C3_1 C 0.41814(5) 0.92032(13) 0.93120(8) 0.0257(2) Uani 1 1 d . . . . .
H3_1 H 0.392676 0.960504 0.961631 0.031 Uiso 1 1 calc R U . . .
C4_1 C 0.40906(5) 0.94105(13) 0.83835(8) 0.0281(3) Uani 1 1 d . . . . .
H4_1 H 0.377448 0.996091 0.804818 0.034 Uiso 1 1 calc R U . . .
C5_1 C 0.44640(5) 0.88103(13) 0.79334(8) 0.0267(2) Uani 1 1 d . . . . .
H5_1 H 0.440100 0.896099 0.729389 0.032 Uiso 1 1 calc R U . . .
C6_1 C 0.49228(5) 0.80014(12) 0.84128(8) 0.0230(2) Uani 1 1 d . . . . .
H6_1 H 0.516860 0.758713 0.809667 0.028 Uiso 1 1 calc R U . . .
C7_1 C 0.50319(4) 0.77812(11) 0.93666(7) 0.0202(2) Uani 1 1 d . . . . .
C1_2 C 0.60328(5) 0.62642(12) 1.16163(7) 0.0208(2) Uani 1 1 d . . . . .
C2_2 C 0.65840(5) 0.67231(12) 1.16973(7) 0.0230(2) Uani 1 1 d . . . . .
H2_2 H 0.665023 0.748748 1.132749 0.028 Uiso 1 1 calc R U . . .
C3_2 C 0.70389(5) 0.60608(13) 1.23214(8) 0.0265(2) Uani 1 1 d . . . . .
H3_2 H 0.741698 0.636963 1.237685 0.032 Uiso 1 1 calc R U . . .
C4_2 C 0.69406(5) 0.49481(13) 1.28634(8) 0.0291(3) Uani 1 1 d . . . . .
H4_2 H 0.725139 0.448420 1.328343 0.035 Uiso 1 1 calc R U . . .
C5_2 C 0.63864(5) 0.45145(13) 1.27901(8) 0.0291(3) Uani 1 1 d . . . . .
H5_2 H 0.631970 0.376110 1.316748 0.035 Uiso 1 1 calc R U . . .
C6_2 C 0.59292(5) 0.51725(12) 1.21702(8) 0.0244(2) Uani 1 1 d . . . . .
H6_2 H 0.555049 0.487995 1.212544 0.029 Uiso 1 1 calc R U . . .
C1_3 C 0.60009(4) 0.61226(11) 0.96253(7) 0.0196(2) Uani 1 1 d . . . . .
C2_3 C 0.62907(5) 0.67963(12) 0.90616(7) 0.0211(2) Uani 1 1 d . . . . .
H2_3 H 0.618470 0.773879 0.884665 0.025 Uiso 1 1 calc R U . . .
C3_3 C 0.67284(5) 0.61155(12) 0.88118(7) 0.0217(2) Uani 1 1 d . . . . .
H3_3 H 0.692144 0.659372 0.843405 0.026 Uiso 1 1 calc R U . . .
C4_3 C 0.68846(5) 0.47292(12) 0.91157(7) 0.0208(2) Uani 1 1 d . . . . .
C5_3 C 0.65916(5) 0.40122(12) 0.96471(7) 0.0219(2) Uani 1 1 d . . . . .
H5_3 H 0.668869 0.305476 0.983781 0.026 Uiso 1 1 calc R U . . .
C6_3 C 0.61568(5) 0.47086(12) 0.98957(7) 0.0213(2) Uani 1 1 d . . . . .
H6_3 H 0.595842 0.421523 1.025956 0.026 Uiso 1 1 calc R U . . .
C1_4 C 0.73682(5) 0.40336(13) 0.88552(8) 0.0252(2) Uani 1 1 d . . . . .
F1_4 F 0.72242(3) 0.35731(9) 0.79884(5) 0.03620(18) Uani 1 1 d . . . . .
F2_4 F 0.78046(3) 0.49379(9) 0.89351(7) 0.0504(2) Uani 1 1 d . . . . .
F3_4 F 0.75783(3) 0.28931(9) 0.93723(5) 0.0406(2) Uani 1 1 d . . . . .
N1_5 N 0.94821(4) 0.66984(10) 0.36244(6) 0.01891(18) Uani 1 1 d . . . . .
C1_5 C 1.02924(5) 0.80303(12) 0.37748(7) 0.0219(2) Uani 1 1 d . . . . .
H1_5 H 1.056438 0.843078 0.350479 0.026 Uiso 1 1 calc R U . . .
B1_5 B 0.94775(5) 0.68868(13) 0.45532(8) 0.0190(2) Uani 1 1 d . . . . .
N2_5 N 0.98836(4) 0.73003(10) 0.32379(6) 0.02178(19) Uani 1 1 d . . . . .
C2_5 C 1.03788(4) 0.83004(11) 0.47411(7) 0.0201(2) Uani 1 1 d . . . . .
C3_5 C 1.08411(5) 0.91183(12) 0.52461(8) 0.0234(2) Uani 1 1 d . . . . .
H3_5 H 1.111650 0.946073 0.496286 0.028 Uiso 1 1 calc R U . . .
C4_5 C 1.08945(5) 0.94235(12) 0.61552(8) 0.0238(2) Uani 1 1 d . . . . .
H4_5 H 1.120771 0.997503 0.649889 0.029 Uiso 1 1 calc R U . . .
C5_5 C 1.04876(5) 0.89218(12) 0.65729(7) 0.0223(2) Uani 1 1 d . . . . .
H5_5 H 1.052152 0.915503 0.719507 0.027 Uiso 1 1 calc R U . . .
C6_5 C 1.00381(4) 0.80916(12) 0.60870(7) 0.0204(2) Uani 1 1 d . . . . .
H6_5 H 0.976929 0.774298 0.638173 0.024 Uiso 1 1 calc R U . . .
C7_5 C 0.99731(4) 0.77547(11) 0.51587(7) 0.0187(2) Uani 1 1 d . . . . .
C1_6 C 0.90546(4) 0.59176(12) 0.29510(7) 0.0197(2) Uani 1 1 d . . . . .
C2_6 C 0.89013(5) 0.45464(12) 0.31509(7) 0.0216(2) Uani 1 1 d . . . . .
H2_6 H 0.908822 0.411050 0.372055 0.026 Uiso 1 1 calc R U . . .
C3_6 C 0.84732(5) 0.38180(12) 0.25127(8) 0.0245(2) Uani 1 1 d . . . . .
H3_6 H 0.836272 0.289009 0.265298 0.029 Uiso 1 1 calc R U . . .
C4_6 C 0.82066(5) 0.44377(13) 0.16728(8) 0.0260(2) Uani 1 1 d . . . . .
H4_6 H 0.791546 0.393569 0.123714 0.031 Uiso 1 1 calc R U . . .
C5_6 C 0.83682(5) 0.57984(13) 0.14725(8) 0.0266(2) Uani 1 1 d . . . . .
H5_6 H 0.818927 0.622166 0.089517 0.032 Uiso 1 1 calc R U . . .
C6_6 C 0.87895(5) 0.65434(12) 0.21107(7) 0.0233(2) Uani 1 1 d . . . . .
H6_6 H 0.889592 0.747672 0.197302 0.028 Uiso 1 1 calc R U . . .
C1_7 C 0.89685(4) 0.63057(11) 0.48966(7) 0.0180(2) Uani 1 1 d . . . . .
C2_7 C 0.90536(4) 0.53293(12) 0.56225(7) 0.0200(2) Uani 1 1 d . . . . .
H2_7 H 0.942713 0.498993 0.590728 0.024 Uiso 1 1 calc R U . . .
C3_7 C 0.86039(5) 0.48462(12) 0.59353(7) 0.0208(2) Uani 1 1 d . . . . .
H3_7 H 0.866794 0.416195 0.641609 0.025 Uiso 1 1 calc R U . . .
C4_7 C 0.80591(5) 0.53731(11) 0.55383(7) 0.0201(2) Uani 1 1 d D . . . .
C5_7 C 0.79620(4) 0.63433(12) 0.48178(7) 0.0210(2) Uani 1 1 d . . . . .
H5_7 H 0.758947 0.670077 0.454720 0.025 Uiso 1 1 calc R U . . .
C6_7 C 0.84121(5) 0.67868(11) 0.44961(7) 0.0201(2) Uani 1 1 d . . . . .
H6_7 H 0.834180 0.743114 0.399294 0.024 Uiso 1 1 calc R U . . .
C1_8 C 0.7593(12) 0.503(5) 0.597(3) 0.0250(17) Uani 0.40(3) 1 d D U P A 1
F1_8 F 0.7078(4) 0.5381(15) 0.5429(9) 0.0429(16) Uani 0.40(3) 1 d . U P A 1
F2_8 F 0.7628(6) 0.5730(16) 0.6737(8) 0.044(2) Uani 0.40(3) 1 d . U P A 1
F3_8 F 0.7583(7) 0.3623(14) 0.6159(13) 0.044(2) Uani 0.40(3) 1 d . U P A 1
C1_81 C 0.7574(8) 0.492(3) 0.5893(17) 0.0250(17) Uani 0.60(3) 1 d D U P A 2
F1_81 F 0.7076(2) 0.4892(16) 0.5241(5) 0.0500(16) Uani 0.60(3) 1 d . U P A 2
F2_81 F 0.7515(5) 0.5818(9) 0.6551(9) 0.0490(16) Uani 0.60(3) 1 d . U P A 2
F3_81 F 0.7634(4) 0.3640(9) 0.6277(7) 0.0343(12) Uani 0.60(3) 1 d . U P A 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
N1_1 N2_1 1.3896(12) . ?
N1_1 B1_1 1.4261(14) . ?
N1_1 C1_2 1.4396(14) . ?
C1_1 N2_1 1.2925(15) . ?
C1_1 C2_1 1.4412(15) . ?
C1_1 H1_1 0.9500 . ?
B1_1 C7_1 1.5375(16) . ?
B1_1 C1_3 1.5774(16) . ?
C2_1 C3_1 1.4029(16) . ?
C2_1 C7_1 1.4133(15) . ?
C3_1 C4_1 1.3781(17) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.4012(17) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3806(16) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.4123(15) . ?
C6_1 H6_1 0.9500 . ?
C1_2 C2_2 1.3874(16) . ?
C1_2 C6_2 1.3895(16) . ?
C2_2 C3_2 1.3900(16) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.3880(17) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.3894(18) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3888(17) . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
C1_3 C2_3 1.4031(15) . ?
C1_3 C6_3 1.4047(15) . ?
C2_3 C3_3 1.3859(16) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.3926(16) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.3910(15) . ?
C4_3 C1_4 1.4965(15) . ?
C5_3 C6_3 1.3859(15) . ?
C5_3 H5_3 0.9500 . ?
C6_3 H6_3 0.9500 . ?
C1_4 F1_4 1.3350(13) . ?
C1_4 F3_4 1.3386(14) . ?
C1_4 F2_4 1.3404(14) . ?
N1_5 N2_5 1.3950(12) . ?
N1_5 B1_5 1.4239(14) . ?
N1_5 C1_6 1.4409(14) . ?
C1_5 N2_5 1.2946(15) . ?
C1_5 C2_5 1.4448(15) . ?
C1_5 H1_5 0.9500 . ?
B1_5 C7_5 1.5338(16) . ?
B1_5 C1_7 1.5743(15) . ?
C2_5 C3_5 1.4029(16) . ?
C2_5 C7_5 1.4131(14) . ?
C3_5 C4_5 1.3792(16) . ?
C3_5 H3_5 0.9500 . ?
C4_5 C5_5 1.4015(16) . ?
C4_5 H4_5 0.9500 . ?
C5_5 C6_5 1.3797(15) . ?
C5_5 H5_5 0.9500 . ?
C6_5 C7_5 1.4090(14) . ?
C6_5 H6_5 0.9500 . ?
C1_6 C6_6 1.3889(15) . ?
C1_6 C2_6 1.3922(16) . ?
C2_6 C3_6 1.3905(16) . ?
C2_6 H2_6 0.9500 . ?
C3_6 C4_6 1.3868(16) . ?
C3_6 H3_6 0.9500 . ?
C4_6 C5_6 1.3903(17) . ?
C4_6 H4_6 0.9500 . ?
C5_6 C6_6 1.3891(16) . ?
C5_6 H5_6 0.9500 . ?
C6_6 H6_6 0.9500 . ?
C1_7 C2_7 1.4009(15) . ?
C1_7 C6_7 1.4011(15) . ?
C2_7 C3_7 1.3893(15) . ?
C2_7 H2_7 0.9500 . ?
C3_7 C4_7 1.3909(15) . ?
C3_7 H3_7 0.9500 . ?
C4_7 C5_7 1.3892(15) . ?
C4_7 C1_81 1.494(8) . ?
C4_7 C1_8 1.498(12) . ?
C5_7 C6_7 1.3863(15) . ?
C5_7 H5_7 0.9500 . ?
C6_7 H6_7 0.9500 . ?
C1_8 F2_8 1.32(4) . ?
C1_8 F1_8 1.34(4) . ?
C1_8 F3_8 1.35(4) . ?
C1_81 F3_81 1.32(3) . ?
C1_81 F1_81 1.34(3) . ?
C1_81 F2_81 1.34(3) . ?

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
N2_1 N1_1 B1_1 125.26(9) . . ?
N2_1 N1_1 C1_2 110.88(8) . . ?
B1_1 N1_1 C1_2 123.85(9) . . ?
N2_1 C1_1 C2_1 126.99(10) . . ?
N2_1 C1_1 H1_1 116.5 . . ?
C2_1 C1_1 H1_1 116.5 . . ?
N1_1 B1_1 C7_1 115.49(10) . . ?
N1_1 B1_1 C1_3 119.16(10) . . ?
C7_1 B1_1 C1_3 125.35(9) . . ?
C1_1 N2_1 N1_1 116.83(9) . . ?
C3_1 C2_1 C7_1 120.97(10) . . ?
C3_1 C2_1 C1_1 120.47(10) . . ?
C7_1 C2_1 C1_1 118.56(10) . . ?
C4_1 C3_1 C2_1 119.88(11) . . ?
C4_1 C3_1 H3_1 120.1 . . ?
C2_1 C3_1 H3_1 120.1 . . ?
C3_1 C4_1 C5_1 120.07(11) . . ?
C3_1 C4_1 H4_1 120.0 . . ?
C5_1 C4_1 H4_1 120.0 . . ?
C6_1 C5_1 C4_1 120.45(11) . . ?
C6_1 C5_1 H5_1 119.8 . . ?
C4_1 C5_1 H5_1 119.8 . . ?
C5_1 C6_1 C7_1 120.94(10) . . ?
C5_1 C6_1 H6_1 119.5 . . ?
C7_1 C6_1 H6_1 119.5 . . ?
C6_1 C7_1 C2_1 117.67(10) . . ?
C6_1 C7_1 B1_1 125.56(10) . . ?
C2_1 C7_1 B1_1 116.77(9) . . ?
C2_2 C1_2 C6_2 120.65(10) . . ?
C2_2 C1_2 N1_1 119.07(10) . . ?
C6_2 C1_2 N1_1 120.25(10) . . ?
C1_2 C2_2 C3_2 119.79(11) . . ?
C1_2 C2_2 H2_2 120.1 . . ?
C3_2 C2_2 H2_2 120.1 . . ?
C4_2 C3_2 C2_2 119.98(11) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 119.82(11) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 120.60(11) . . ?
C6_2 C5_2 H5_2 119.7 . . ?
C4_2 C5_2 H5_2 119.7 . . ?
C5_2 C6_2 C1_2 119.14(11) . . ?
C5_2 C6_2 H6_2 120.4 . . ?
C1_2 C6_2 H6_2 120.4 . . ?
C2_3 C1_3 C6_3 117.27(10) . . ?
C2_3 C1_3 B1_1 121.59(10) . . ?
C6_3 C1_3 B1_1 121.10(10) . . ?
C3_3 C2_3 C1_3 121.38(10) . . ?
C3_3 C2_3 H2_3 119.3 . . ?
C1_3 C2_3 H2_3 119.3 . . ?
C2_3 C3_3 C4_3 119.88(10) . . ?
C2_3 C3_3 H3_3 120.1 . . ?
C4_3 C3_3 H3_3 120.1 . . ?
C5_3 C4_3 C3_3 120.14(10) . . ?
C5_3 C4_3 C1_4 121.12(10) . . ?
C3_3 C4_3 C1_4 118.74(10) . . ?
C6_3 C5_3 C4_3 119.34(10) . . ?
C6_3 C5_3 H5_3 120.3 . . ?
C4_3 C5_3 H5_3 120.3 . . ?
C5_3 C6_3 C1_3 121.92(10) . . ?
C5_3 C6_3 H6_3 119.0 . . ?
C1_3 C6_3 H6_3 119.0 . . ?
F1_4 C1_4 F3_4 105.91(9) . . ?
F1_4 C1_4 F2_4 106.11(10) . . ?
F3_4 C1_4 F2_4 106.43(10) . . ?
F1_4 C1_4 C4_3 112.91(9) . . ?
F3_4 C1_4 C4_3 113.18(10) . . ?
F2_4 C1_4 C4_3 111.76(10) . . ?
N2_5 N1_5 B1_5 124.56(9) . . ?
N2_5 N1_5 C1_6 111.27(8) . . ?
B1_5 N1_5 C1_6 124.10(9) . . ?
N2_5 C1_5 C2_5 126.89(10) . . ?
N2_5 C1_5 H1_5 116.6 . . ?
C2_5 C1_5 H1_5 116.6 . . ?
N1_5 B1_5 C7_5 115.83(9) . . ?
N1_5 B1_5 C1_7 120.68(10) . . ?
C7_5 B1_5 C1_7 123.38(9) . . ?
C1_5 N2_5 N1_5 117.30(9) . . ?
C3_5 C2_5 C7_5 120.77(10) . . ?
C3_5 C2_5 C1_5 121.18(10) . . ?
C7_5 C2_5 C1_5 118.02(10) . . ?
C4_5 C3_5 C2_5 119.78(10) . . ?
C4_5 C3_5 H3_5 120.1 . . ?
C2_5 C3_5 H3_5 120.1 . . ?
C3_5 C4_5 C5_5 120.15(10) . . ?
C3_5 C4_5 H4_5 119.9 . . ?
C5_5 C4_5 H4_5 119.9 . . ?
C6_5 C5_5 C4_5 120.46(10) . . ?
C6_5 C5_5 H5_5 119.8 . . ?
C4_5 C5_5 H5_5 119.8 . . ?
C5_5 C6_5 C7_5 120.76(10) . . ?
C5_5 C6_5 H6_5 119.6 . . ?
C7_5 C6_5 H6_5 119.6 . . ?
C6_5 C7_5 C2_5 118.04(10) . . ?
C6_5 C7_5 B1_5 124.59(9) . . ?
C2_5 C7_5 B1_5 117.31(9) . . ?
C6_6 C1_6 C2_6 120.17(10) . . ?
C6_6 C1_6 N1_5 119.95(10) . . ?
C2_6 C1_6 N1_5 119.86(9) . . ?
C3_6 C2_6 C1_6 119.68(10) . . ?
C3_6 C2_6 H2_6 120.2 . . ?
C1_6 C2_6 H2_6 120.2 . . ?
C4_6 C3_6 C2_6 120.41(11) . . ?
C4_6 C3_6 H3_6 119.8 . . ?
C2_6 C3_6 H3_6 119.8 . . ?
C3_6 C4_6 C5_6 119.57(11) . . ?
C3_6 C4_6 H4_6 120.2 . . ?
C5_6 C4_6 H4_6 120.2 . . ?
C6_6 C5_6 C4_6 120.46(10) . . ?
C6_6 C5_6 H5_6 119.8 . . ?
C4_6 C5_6 H5_6 119.8 . . ?
C1_6 C6_6 C5_6 119.70(11) . . ?
C1_6 C6_6 H6_6 120.2 . . ?
C5_6 C6_6 H6_6 120.2 . . ?
C2_7 C1_7 C6_7 117.65(10) . . ?
C2_7 C1_7 B1_5 121.81(9) . . ?
C6_7 C1_7 B1_5 120.53(9) . . ?
C3_7 C2_7 C1_7 121.47(10) . . ?
C3_7 C2_7 H2_7 119.3 . . ?
C1_7 C2_7 H2_7 119.3 . . ?
C2_7 C3_7 C4_7 119.42(10) . . ?
C2_7 C3_7 H3_7 120.3 . . ?
C4_7 C3_7 H3_7 120.3 . . ?
C5_7 C4_7 C3_7 120.35(10) . . ?
C5_7 C4_7 C1_81 119.3(11) . . ?
C3_7 C4_7 C1_81 120.3(11) . . ?
C5_7 C4_7 C1_8 120.0(17) . . ?
C3_7 C4_7 C1_8 119.3(16) . . ?
C6_7 C5_7 C4_7 119.60(10) . . ?
C6_7 C5_7 H5_7 120.2 . . ?
C4_7 C5_7 H5_7 120.2 . . ?
C5_7 C6_7 C1_7 121.47(10) . . ?
C5_7 C6_7 H6_7 119.3 . . ?
C1_7 C6_7 H6_7 119.3 . . ?
F2_8 C1_8 F1_8 104(2) . . ?
F2_8 C1_8 F3_8 107(2) . . ?
F1_8 C1_8 F3_8 108(2) . . ?
F2_8 C1_8 C4_7 114(2) . . ?
F1_8 C1_8 C4_7 112(2) . . ?
F3_8 C1_8 C4_7 111(3) . . ?
F3_81 C1_81 F1_81 105.9(15) . . ?
F3_81 C1_81 F2_81 105.0(15) . . ?
F1_81 C1_81 F2_81 107.3(16) . . ?
F3_81 C1_81 C4_7 114.4(17) . . ?
F1_81 C1_81 C4_7 113.0(15) . . ?
F2_81 C1_81 C4_7 110.6(16) . . ?

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
N2_1 N1_1 B1_1 C7_1 3.98(15) . . . . ?
C1_2 N1_1 B1_1 C7_1 -174.83(9) . . . . ?
N2_1 N1_1 B1_1 C1_3 -175.89(9) . . . . ?
C1_2 N1_1 B1_1 C1_3 5.30(15) . . . . ?
C2_1 C1_1 N2_1 N1_1 0.49(17) . . . . ?
B1_1 N1_1 N2_1 C1_1 -3.42(15) . . . . ?
C1_2 N1_1 N2_1 C1_1 175.53(10) . . . . ?
N2_1 C1_1 C2_1 C3_1 -178.55(11) . . . . ?
N2_1 C1_1 C2_1 C7_1 1.49(17) . . . . ?
C7_1 C2_1 C3_1 C4_1 -0.51(17) . . . . ?
C1_1 C2_1 C3_1 C4_1 179.54(11) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.41(18) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.39(18) . . . . ?
C4_1 C5_1 C6_1 C7_1 -1.10(17) . . . . ?
C5_1 C6_1 C7_1 C2_1 0.98(16) . . . . ?
C5_1 C6_1 C7_1 B1_1 -178.48(10) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.18(15) . . . . ?
C1_1 C2_1 C7_1 C6_1 179.77(10) . . . . ?
C3_1 C2_1 C7_1 B1_1 179.32(10) . . . . ?
C1_1 C2_1 C7_1 B1_1 -0.72(15) . . . . ?
N1_1 B1_1 C7_1 C6_1 177.74(10) . . . . ?
C1_3 B1_1 C7_1 C6_1 -2.40(17) . . . . ?
N1_1 B1_1 C7_1 C2_1 -1.72(14) . . . . ?
C1_3 B1_1 C7_1 C2_1 178.14(10) . . . . ?
N2_1 N1_1 C1_2 C2_2 -123.06(10) . . . . ?
B1_1 N1_1 C1_2 C2_2 55.91(14) . . . . ?
N2_1 N1_1 C1_2 C6_2 59.04(13) . . . . ?
B1_1 N1_1 C1_2 C6_2 -121.99(12) . . . . ?
C6_2 C1_2 C2_2 C3_2 1.70(16) . . . . ?
N1_1 C1_2 C2_2 C3_2 -176.19(9) . . . . ?
C1_2 C2_2 C3_2 C4_2 -0.26(17) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.99(18) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.83(18) . . . . ?
C4_2 C5_2 C6_2 C1_2 0.59(17) . . . . ?
C2_2 C1_2 C6_2 C5_2 -1.86(16) . . . . ?
N1_1 C1_2 C6_2 C5_2 176.01(10) . . . . ?
N1_1 B1_1 C1_3 C2_3 -129.83(11) . . . . ?
C7_1 B1_1 C1_3 C2_3 50.32(15) . . . . ?
N1_1 B1_1 C1_3 C6_3 47.76(15) . . . . ?
C7_1 B1_1 C1_3 C6_3 -132.09(11) . . . . ?
C6_3 C1_3 C2_3 C3_3 -2.52(15) . . . . ?
B1_1 C1_3 C2_3 C3_3 175.16(10) . . . . ?
C1_3 C2_3 C3_3 C4_3 0.56(16) . . . . ?
C2_3 C3_3 C4_3 C5_3 1.84(16) . . . . ?
C2_3 C3_3 C4_3 C1_4 -178.48(10) . . . . ?
C3_3 C4_3 C5_3 C6_3 -2.16(16) . . . . ?
C1_4 C4_3 C5_3 C6_3 178.16(10) . . . . ?
C4_3 C5_3 C6_3 C1_3 0.11(16) . . . . ?
C2_3 C1_3 C6_3 C5_3 2.19(15) . . . . ?
B1_1 C1_3 C6_3 C5_3 -175.50(10) . . . . ?
C5_3 C4_3 C1_4 F1_4 103.03(12) . . . . ?
C3_3 C4_3 C1_4 F1_4 -76.65(13) . . . . ?
C5_3 C4_3 C1_4 F3_4 -17.28(15) . . . . ?
C3_3 C4_3 C1_4 F3_4 163.04(10) . . . . ?
C5_3 C4_3 C1_4 F2_4 -137.43(11) . . . . ?
C3_3 C4_3 C1_4 F2_4 42.89(14) . . . . ?
N2_5 N1_5 B1_5 C7_5 -3.27(15) . . . . ?
C1_6 N1_5 B1_5 C7_5 179.99(9) . . . . ?
N2_5 N1_5 B1_5 C1_7 173.17(9) . . . . ?
C1_6 N1_5 B1_5 C1_7 -3.58(16) . . . . ?
C2_5 C1_5 N2_5 N1_5 -0.33(16) . . . . ?
B1_5 N1_5 N2_5 C1_5 3.00(15) . . . . ?
C1_6 N1_5 N2_5 C1_5 -179.89(9) . . . . ?
N2_5 C1_5 C2_5 C3_5 -179.77(11) . . . . ?
N2_5 C1_5 C2_5 C7_5 -1.77(17) . . . . ?
C7_5 C2_5 C3_5 C4_5 -1.52(16) . . . . ?
C1_5 C2_5 C3_5 C4_5 176.42(10) . . . . ?
C2_5 C3_5 C4_5 C5_5 -0.16(17) . . . . ?
C3_5 C4_5 C5_5 C6_5 1.53(17) . . . . ?
C4_5 C5_5 C6_5 C7_5 -1.21(16) . . . . ?
C5_5 C6_5 C7_5 C2_5 -0.45(15) . . . . ?
C5_5 C6_5 C7_5 B1_5 -177.72(10) . . . . ?
C3_5 C2_5 C7_5 C6_5 1.81(15) . . . . ?
C1_5 C2_5 C7_5 C6_5 -176.19(10) . . . . ?
C3_5 C2_5 C7_5 B1_5 179.29(10) . . . . ?
C1_5 C2_5 C7_5 B1_5 1.28(14) . . . . ?
N1_5 B1_5 C7_5 C6_5 178.27(10) . . . . ?
C1_7 B1_5 C7_5 C6_5 1.94(16) . . . . ?
N1_5 B1_5 C7_5 C2_5 0.98(14) . . . . ?
C1_7 B1_5 C7_5 C2_5 -175.35(10) . . . . ?
N2_5 N1_5 C1_6 C6_6 -48.59(13) . . . . ?
B1_5 N1_5 C1_6 C6_6 128.53(11) . . . . ?
N2_5 N1_5 C1_6 C2_6 132.51(10) . . . . ?
B1_5 N1_5 C1_6 C2_6 -50.37(14) . . . . ?
C6_6 C1_6 C2_6 C3_6 -1.34(16) . . . . ?
N1_5 C1_6 C2_6 C3_6 177.56(9) . . . . ?
C1_6 C2_6 C3_6 C4_6 1.28(17) . . . . ?
C2_6 C3_6 C4_6 C5_6 -0.28(17) . . . . ?
C3_6 C4_6 C5_6 C6_6 -0.68(17) . . . . ?
C2_6 C1_6 C6_6 C5_6 0.40(16) . . . . ?
N1_5 C1_6 C6_6 C5_6 -178.50(10) . . . . ?
C4_6 C5_6 C6_6 C1_6 0.62(17) . . . . ?
N1_5 B1_5 C1_7 C2_7 122.14(11) . . . . ?
C7_5 B1_5 C1_7 C2_7 -61.70(15) . . . . ?
N1_5 B1_5 C1_7 C6_7 -59.64(14) . . . . ?
C7_5 B1_5 C1_7 C6_7 116.52(11) . . . . ?
C6_7 C1_7 C2_7 C3_7 0.25(15) . . . . ?
B1_5 C1_7 C2_7 C3_7 178.52(10) . . . . ?
C1_7 C2_7 C3_7 C4_7 -1.91(16) . . . . ?
C2_7 C3_7 C4_7 C5_7 1.82(16) . . . . ?
C2_7 C3_7 C4_7 C1_81 -177.1(12) . . . . ?
C2_7 C3_7 C4_7 C1_8 -170.7(18) . . . . ?
C3_7 C4_7 C5_7 C6_7 -0.08(16) . . . . ?
C1_81 C4_7 C5_7 C6_7 178.9(12) . . . . ?
C1_8 C4_7 C5_7 C6_7 172.4(18) . . . . ?
C4_7 C5_7 C6_7 C1_7 -1.62(16) . . . . ?
C2_7 C1_7 C6_7 C5_7 1.53(15) . . . . ?
B1_5 C1_7 C6_7 C5_7 -176.76(10) . . . . ?
C5_7 C4_7 C1_8 F2_8 -99(3) . . . . ?
C3_7 C4_7 C1_8 F2_8 74(3) . . . . ?
C5_7 C4_7 C1_8 F1_8 19(4) . . . . ?
C3_7 C4_7 C1_8 F1_8 -168.8(19) . . . . ?
C5_7 C4_7 C1_8 F3_8 140(2) . . . . ?
C3_7 C4_7 C1_8 F3_8 -48(3) . . . . ?
C5_7 C4_7 C1_81 F3_81 153.4(13) . . . . ?
C3_7 C4_7 C1_81 F3_81 -28(2) . . . . ?
C5_7 C4_7 C1_81 F1_81 32(2) . . . . ?
C3_7 C4_7 C1_81 F1_81 -149.0(14) . . . . ?
C5_7 C4_7 C1_81 F2_81 -88.3(18) . . . . ?
C3_7 C4_7 C1_81 F2_81 91(2) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-Li
_database_code_depnum_ccdc_archive 'CCDC 2394204'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.5e (K.Radacki, 2005-23)'
_audit_creation_date             2024-09-20
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C33 H40 B Li N2 O2'
_chemical_formula_sum            'C33 H40 B Li N2 O2'
_chemical_formula_weight         514.42
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'
Li Li 0.0008 0.0003 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'


_cell_length_a                   11.2851(2)
_cell_length_b                   15.5100(2)
_cell_length_c                   17.2399(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3017.53(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13024
_cell_measurement_theta_min      4.6610
_cell_measurement_theta_max      73.3010

_exptl_crystal_description       block
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.115
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 1 0.0837
1 2 -1 0.0862
1 -1 -2 0.0753
0 -1 0 0.0931
0 1 0 0.0615
1 -1 -1 0.0683
-1 1 1 0.0788
-1 -2 2 0.0940
1 2 -2 0.0911
-1 2 0 0.0565
1 -2 0 0.0741
1 0 -1 0.0726
-1 0 1 0.0726
2 -1 -1 0.0629
-1 1 0 0.0465
1 -2 2 0.0920
2 -1 0 0.0712
-2 1 -2 0.0618
1 -1 2 0.0954
2 -1 2 0.0829
-1 0 -1 0.0505
1 0 1 0.0728
-2 -1 0 0.0487
2 1 0 0.0663
0 0 1 0.0864
0 0 -1 0.0838
-1 -1 -2 0.0596

_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.942
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     38.00 103.00   0.50    0.17    --   85.25-131.00-146.26  130
  2  ω     39.00 107.00   0.50    0.17    --   85.25-137.00 -76.05  136
  3  ω     41.00  66.00   0.50    0.17    --   85.25-106.00 -57.56   50
  4  ω     60.00  91.00   0.50    0.17    --   85.25 -95.00 -36.61   62
  5  ω     14.00  70.00   0.50    0.05    --   58.60-101.00  47.00  112
  6  ω     27.00  83.00   0.50    0.05    --   71.26-101.00  47.00  112
  7  ω     44.00  69.00   0.50    0.17    --   85.25 -95.00  57.00   50
  8  ω     38.00  92.00   0.50    0.17    --   82.35-101.00  47.00  108
  9  ω     43.00  89.00   0.50    0.17    --   85.25 -98.00  75.18   92
 10  ω     44.00  70.00   0.50    0.17    --   85.25 -73.00-110.28   52
 11  ω     17.00  43.00   0.50    0.05    --    6.00  64.00 130.22   52
 12  ω     30.00  60.00   0.50    0.05    --   18.00  57.00 -25.52   60
 13  ω    107.00 133.00   0.50    0.17    --   85.25  49.00 122.15   52
 14  ω     97.00 136.00   0.50    0.17    --   85.25  40.00 118.37   78
 15  ω     97.00 132.00   0.50    0.17    --   85.25  58.00  36.47   70
 16  ω     97.00 132.00   0.50    0.17    --   85.25  59.00-156.87   70
 17  ω     95.00 120.00   0.50    0.17    --   85.25 128.00 -62.24   50
 18  ω    100.00 131.00   0.50    0.17    --   85.25 119.00-140.01   62
 19  ω    102.00 128.00   0.50    0.17    --   85.25 117.00 -32.52   52
 20  ω     97.00 132.00   0.50    0.17    --   85.25 125.00 139.08   70
 21  ω      4.00  30.00   0.50    0.05    --   -6.00  69.00  13.00   52
 22  ω     -6.00  20.00   0.50    0.05    --  -10.00  78.00 117.66   52
 23  ω    -72.00 -16.00   0.50    0.05    --  -60.30 101.00 151.00  112
 24  ω    -81.00 -26.00   0.50    0.05    --  -69.94 101.00 151.00  110
 25  ω    -88.00 -32.00   0.50    0.17    --  -76.30 101.00 151.00  112
 26  ω   -124.00 -94.00   0.50    0.17    --  -79.50 -64.00 -65.28   60
 27  ω   -127.00 -92.00   0.50    0.17    --  -79.50 -54.00 -32.10   70
 28  ω   -128.00 -93.00   0.50    0.17    --  -79.50 -49.00  -8.10   70
 29  ω   -124.00 -92.00   0.50    0.17    --  -79.50 -63.00  80.70   64
 30  ω   -123.00 -88.00   0.50    0.17    --  -74.00 -50.00 132.33   70
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.1007011000
_diffrn_orient_matrix_UB_12      -0.0157382000
_diffrn_orient_matrix_UB_13      0.0589290000
_diffrn_orient_matrix_UB_21      -0.0126302000
_diffrn_orient_matrix_UB_22      0.0930357000
_diffrn_orient_matrix_UB_23      0.0297657000
_diffrn_orient_matrix_UB_31      -0.0913027000
_diffrn_orient_matrix_UB_32      -0.0303771000
_diffrn_orient_matrix_UB_33      0.0606398000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            29040
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.834
_diffrn_reflns_theta_max         75.332
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6015
_reflns_number_gt                5432
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.971
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences. Completness statistics refer to single and composite 
 reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Refined as a 2-component inversion twin. The BASF parameter was refined to 
 34.7%. The diethylether molecules are disordered. The atomic displacement 
 parameters of atoms O1_1 > C4_21 were restrained with RIGU keyword with esd 
 = 0.008 in ShelXL input ('enhanced rigid bond' restraint for all bonds in 
 the connectivity list). The displacement parameters of atoms O1_1 > C4_21 
 were restrained to the same value with similarity restraint SIMU with esd = 
 0.004. The Uii displacement parameters of atoms O1_1 > C4_21 were 
 restrained with ISOR keyword with esd = 0.004 to approximate isotropic 
 behavior. The distances between the diethylether atoms C1 to C2 and c3 to 
 C4, O to C1 and O1 to C3, O1 to C2 and O1 to C4 were restrained to the value 
 of 1.53 (esd = 0.005), 1.38 (esd = 0.005) and 2.38 (esd = 0.005)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0955P)²+1.3489P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.3(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6015
_refine_ls_number_parameters     445
_refine_ls_number_restraints     480
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.051
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 0.5869(2) 0.52799(18) 0.62361(15) 0.0294(6) Uani 1 1 d . . . . .
C1 C 0.4180(3) 0.4477(2) 0.60757(19) 0.0334(7) Uani 1 1 d . . . . .
H1 H 0.334643 0.442925 0.614215 0.040 Uiso 1 1 calc R U . . .
Li1 Li 0.3890(6) 0.6083(4) 0.7000(4) 0.0443(15) Uani 1 1 d . . . . .
B1 B 0.6452(3) 0.4921(2) 0.5466(2) 0.0292(7) Uani 1 1 d . . . . .
N2 N 0.4697(2) 0.51305(19) 0.64057(15) 0.0304(6) Uani 1 1 d . . . . .
C2 C 0.4750(3) 0.3815(2) 0.56174(19) 0.0333(7) Uani 1 1 d . . . . .
C3 C 0.5914(3) 0.3961(2) 0.53657(18) 0.0317(7) Uani 1 1 d . . . . .
C4 C 0.6486(3) 0.3263(2) 0.5009(2) 0.0406(8) Uani 1 1 d . . . . .
H4 H 0.728703 0.332922 0.484965 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4766(4) 0.2363(3) 0.5118(3) 0.0499(10) Uani 1 1 d . . . . .
H6 H 0.437852 0.182843 0.502984 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7242(3) 0.6452(2) 0.6516(2) 0.0376(8) Uani 1 1 d . . . . .
H11 H 0.747535 0.647012 0.598647 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7895(3) 0.4880(2) 0.55408(19) 0.0295(6) Uani 1 1 d . . . . .
C8 C 0.6383(3) 0.5861(2) 0.67619(19) 0.0320(7) Uani 1 1 d . . . . .
C9 C 0.6025(3) 0.5489(2) 0.47180(18) 0.0315(7) Uani 1 1 d . . . . .
C7 C 0.4173(3) 0.3035(3) 0.5486(2) 0.0435(9) Uani 1 1 d . . . . .
H7 H 0.337463 0.296162 0.564855 0.052 Uiso 1 1 calc R U . . .
C5 C 0.5929(4) 0.2485(3) 0.4880(3) 0.0497(10) Uani 1 1 d . . . . .
H5 H 0.634257 0.203020 0.462864 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7748(4) 0.7006(3) 0.7045(3) 0.0513(11) Uani 1 1 d . . . . .
H12 H 0.832750 0.740762 0.687371 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7432(4) 0.6993(3) 0.7823(3) 0.0572(12) Uani 1 1 d . . . . .
H13 H 0.780141 0.737420 0.818016 0.069 Uiso 1 1 calc R U . . .
C14 C 0.6578(4) 0.6422(3) 0.8071(2) 0.0513(10) Uani 1 1 d . . . . .
H14 H 0.634165 0.641781 0.860020 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6062(3) 0.5850(3) 0.7550(2) 0.0375(8) Uani 1 1 d . . . . .
H15 H 0.548695 0.544901 0.772708 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6215(3) 0.5183(3) 0.3964(2) 0.0371(7) Uani 1 1 d . . . . .
H16 H 0.657080 0.463283 0.389842 0.045 Uiso 1 1 calc R U . . .
C17 C 0.5902(3) 0.5655(3) 0.3306(2) 0.0426(9) Uani 1 1 d . . . . .
H17 H 0.605514 0.542934 0.280300 0.051 Uiso 1 1 calc R U . . .
C18 C 0.5370(3) 0.6449(3) 0.3389(2) 0.0433(9) Uani 1 1 d . . . . .
H18 H 0.515805 0.677625 0.294432 0.052 Uiso 1 1 calc R U . . .
C19 C 0.5148(3) 0.6766(3) 0.4127(2) 0.0405(8) Uani 1 1 d . . . . .
H19 H 0.476568 0.730714 0.418829 0.049 Uiso 1 1 calc R U . . .
C20 C 0.5481(3) 0.6295(2) 0.4778(2) 0.0346(7) Uani 1 1 d . . . . .
H20 H 0.533380 0.652914 0.527816 0.041 Uiso 1 1 calc R U . . .
C21 C 0.8435(3) 0.4435(2) 0.61533(19) 0.0346(7) Uani 1 1 d . . . . .
H21 H 0.795032 0.415723 0.652816 0.042 Uiso 1 1 calc R U . . .
C22 C 0.9662(3) 0.4388(3) 0.6228(2) 0.0399(8) Uani 1 1 d . . . . .
H22 H 1.000189 0.407810 0.664894 0.048 Uiso 1 1 calc R U . . .
C23 C 1.0388(3) 0.4790(3) 0.5693(2) 0.0426(9) Uani 1 1 d . . . . .
H23 H 1.122486 0.476551 0.575022 0.051 Uiso 1 1 calc R U . . .
C24 C 0.9897(3) 0.5223(3) 0.5079(3) 0.0450(9) Uani 1 1 d . . . . .
H24 H 1.039171 0.549075 0.470424 0.054 Uiso 1 1 calc R U . . .
C25 C 0.8663(3) 0.5268(2) 0.5009(2) 0.0376(8) Uani 1 1 d . . . . .
H25 H 0.833395 0.557419 0.458258 0.045 Uiso 1 1 calc R U . . .
O1_1 O 0.3890(4) 0.7195(3) 0.6515(3) 0.0470(10) Uani 0.712(7) 1 d D U P A 1
C1_1 C 0.4625(5) 0.7854(4) 0.6784(4) 0.0549(13) Uani 0.712(7) 1 d D U P A 1
H4A_1 H 0.487724 0.821789 0.634264 0.066 Uiso 0.712(7) 1 calc R U P A 1
H4AB_1 H 0.534291 0.759929 0.702156 0.066 Uiso 0.712(7) 1 calc R U P A 1
C2_1 C 0.3995(8) 0.8404(5) 0.7375(5) 0.082(2) Uani 0.712(7) 1 d D U P A 1
H5A_1 H 0.452897 0.886080 0.755511 0.098 Uiso 0.712(7) 1 calc R U P A 1
H5B_1 H 0.329094 0.866394 0.713849 0.098 Uiso 0.712(7) 1 calc R U P A 1
H5C_1 H 0.375610 0.804603 0.781668 0.098 Uiso 0.712(7) 1 calc R U P A 1
C3_1 C 0.3189(11) 0.7458(5) 0.5876(5) 0.0436(13) Uani 0.712(7) 1 d D U P A 1
H6A_1 H 0.370564 0.765505 0.544727 0.052 Uiso 0.712(7) 1 calc R U P A 1
H6AB_1 H 0.266955 0.794266 0.603037 0.052 Uiso 0.712(7) 1 calc R U P A 1
C4_1 C 0.2440(10) 0.6697(9) 0.5610(6) 0.056(2) Uani 0.712(7) 1 d D U P A 1
H7A_1 H 0.195064 0.687114 0.516740 0.084 Uiso 0.712(7) 1 calc R U P A 1
H7B_1 H 0.296045 0.622091 0.545470 0.084 Uiso 0.712(7) 1 calc R U P A 1
H7C_1 H 0.192750 0.650765 0.603603 0.084 Uiso 0.712(7) 1 calc R U P A 1
O1_11 O 0.3578(12) 0.7229(9) 0.6659(8) 0.0503(15) Uani 0.288(7) 1 d D U P A 2
C1_11 C 0.3777(13) 0.7863(9) 0.7209(8) 0.0575(17) Uani 0.288(7) 1 d D U P A 2
H4A_11 H 0.393875 0.759113 0.771744 0.069 Uiso 0.288(7) 1 calc R U P A 2
H4AB_11 H 0.305971 0.822520 0.726195 0.069 Uiso 0.288(7) 1 calc R U P A 2
C2_11 C 0.4825(15) 0.8427(10) 0.6978(11) 0.073(3) Uani 0.288(7) 1 d D U P A 2
H5A_11 H 0.495092 0.887075 0.737379 0.110 Uiso 0.288(7) 1 calc R U P A 2
H5B_11 H 0.553824 0.806972 0.693272 0.110 Uiso 0.288(7) 1 calc R U P A 2
H5C_11 H 0.466036 0.870294 0.647784 0.110 Uiso 0.288(7) 1 calc R U P A 2
C3_11 C 0.313(3) 0.7529(13) 0.5958(13) 0.0467(18) Uani 0.288(7) 1 d D U P A 2
H6A_11 H 0.377920 0.780039 0.565598 0.056 Uiso 0.288(7) 1 calc R U P A 2
H6AB_11 H 0.251889 0.797048 0.605691 0.056 Uiso 0.288(7) 1 calc R U P A 2
C4_11 C 0.260(2) 0.679(2) 0.5495(11) 0.042(3) Uani 0.288(7) 1 d D U P A 2
H7A_11 H 0.229053 0.700679 0.500176 0.050 Uiso 0.288(7) 1 calc R U P A 2
H7B_11 H 0.321299 0.635404 0.539189 0.050 Uiso 0.288(7) 1 calc R U P A 2
H7C_11 H 0.195492 0.652382 0.579210 0.050 Uiso 0.288(7) 1 calc R U P A 2
O1_2 O 0.2606(7) 0.5845(5) 0.7695(5) 0.0729(14) Uani 0.558(6) 1 d D U P A 1
C1_2 C 0.1488(8) 0.6210(8) 0.7619(5) 0.0847(17) Uani 0.558(6) 1 d D U P A 1
H9A_2 H 0.089487 0.574583 0.755104 0.102 Uiso 0.558(6) 1 calc R U P A 1
H9AB_2 H 0.147034 0.657639 0.714864 0.102 Uiso 0.558(6) 1 calc R U P A 1
C2_2 C 0.1154(11) 0.6752(7) 0.8320(6) 0.088(3) Uani 0.558(6) 1 d D U P A 1
H10A_2 H 0.036186 0.699679 0.824296 0.105 Uiso 0.558(6) 1 calc R U P A 1
H10B_2 H 0.115458 0.638940 0.878502 0.105 Uiso 0.558(6) 1 calc R U P A 1
H10C_2 H 0.172989 0.721973 0.838273 0.105 Uiso 0.558(6) 1 calc R U P A 1
C3_2 C 0.2255(10) 0.5037(5) 0.7920(5) 0.0778(17) Uani 0.558(6) 1 d D U P A 1
H11A_2 H 0.273275 0.459935 0.764382 0.093 Uiso 0.558(6) 1 calc R U P A 1
H11B_2 H 0.141299 0.494953 0.777917 0.093 Uiso 0.558(6) 1 calc R U P A 1
C4_2 C 0.2405(11) 0.4921(8) 0.8793(5) 0.093(3) Uani 0.558(6) 1 d D U P A 1
H12A_2 H 0.214957 0.434026 0.894112 0.139 Uiso 0.558(6) 1 calc R U P A 1
H12B_2 H 0.324049 0.499940 0.893156 0.139 Uiso 0.558(6) 1 calc R U P A 1
H12C_2 H 0.192242 0.534913 0.906674 0.139 Uiso 0.558(6) 1 calc R U P A 1
O1_21 O 0.2747(9) 0.5943(6) 0.7847(6) 0.0745(15) Uani 0.442(6) 1 d D U P A 2
C1_21 C 0.2036(9) 0.6641(7) 0.8066(8) 0.0822(18) Uani 0.442(6) 1 d D U P A 2
H9A_21 H 0.229449 0.716773 0.778858 0.099 Uiso 0.442(6) 1 calc R U P A 2
H9AB_21 H 0.211405 0.674536 0.862995 0.099 Uiso 0.442(6) 1 calc R U P A 2
C2_21 C 0.0735(8) 0.6440(11) 0.7865(10) 0.093(3) Uani 0.442(6) 1 d D U P A 2
H10A_21 H 0.023440 0.692815 0.801671 0.139 Uiso 0.442(6) 1 calc R U P A 2
H10B_21 H 0.066188 0.634336 0.730496 0.139 Uiso 0.442(6) 1 calc R U P A 2
H10C_21 H 0.048192 0.592210 0.814411 0.139 Uiso 0.442(6) 1 calc R U P A 2
C3_21 C 0.2818(14) 0.5426(7) 0.8499(6) 0.0825(18) Uani 0.442(6) 1 d D U P A 2
H11A_21 H 0.212986 0.553258 0.884231 0.099 Uiso 0.442(6) 1 calc R U P A 2
H11B_21 H 0.355070 0.555630 0.879160 0.099 Uiso 0.442(6) 1 calc R U P A 2
C4_21 C 0.2825(14) 0.4476(6) 0.8229(9) 0.090(3) Uani 0.442(6) 1 d D U P A 2
H12A_21 H 0.287470 0.409650 0.868225 0.134 Uiso 0.442(6) 1 calc R U P A 2
H12B_21 H 0.209468 0.435307 0.794217 0.134 Uiso 0.442(6) 1 calc R U P A 2
H12C_21 H 0.351030 0.437670 0.789165 0.134 Uiso 0.442(6) 1 calc R U P A 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
N1 N2 1.375(3) . ?
N1 C8 1.404(4) . ?
N1 B1 1.582(4) . ?
C1 N2 1.301(4) . ?
C1 C2 1.446(5) . ?
C1 H1 0.9500 . ?
Li1 O1_11 1.905(17) . ?
Li1 O1_2 1.916(10) . ?
Li1 O1_1 1.918(9) . ?
Li1 O1_21 1.961(12) . ?
Li1 N2 2.015(7) . ?
Li1 C15 2.652(8) . ?
Li1 C1_11 2.787(15) . ?
B1 C3 1.617(5) . ?
B1 C9 1.635(5) . ?
B1 C10 1.635(4) . ?
C2 C7 1.392(5) . ?
C2 C3 1.402(4) . ?
C3 C4 1.402(5) . ?
C4 C5 1.379(5) . ?
C4 H4 0.9500 . ?
C6 C5 1.388(5) . ?
C6 C7 1.392(5) . ?
C6 H6 0.9500 . ?
C11 C12 1.378(5) . ?
C11 C8 1.399(5) . ?
C11 H11 0.9500 . ?
C10 C25 1.398(5) . ?
C10 C21 1.401(5) . ?
C8 C15 1.406(5) . ?
C9 C20 1.397(5) . ?
C9 C16 1.400(5) . ?
C7 H7 0.9500 . ?
C5 H5 0.9500 . ?
C12 C13 1.387(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.396(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.393(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.370(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.401(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
O1_1 C1_1 1.395(5) . ?
O1_1 C3_1 1.415(5) . ?
C1_1 C2_1 1.507(6) . ?
C1_1 H4A_1 0.9900 . ?
C1_1 H4AB_1 0.9900 . ?
C2_1 H5A_1 0.9800 . ?
C2_1 H5B_1 0.9800 . ?
C2_1 H5C_1 0.9800 . ?
C3_1 C4_1 1.523(6) . ?
C3_1 H6A_1 0.9900 . ?
C3_1 H6AB_1 0.9900 . ?
C4_1 H7A_1 0.9800 . ?
C4_1 H7B_1 0.9800 . ?
C4_1 H7C_1 0.9800 . ?
O1_11 C1_11 1.384(7) . ?
O1_11 C3_11 1.388(7) . ?
C1_11 C2_11 1.524(7) . ?
C1_11 H4A_11 0.9900 . ?
C1_11 H4AB_11 0.9900 . ?
C2_11 H5A_11 0.9800 . ?
C2_11 H5B_11 0.9800 . ?
C2_11 H5C_11 0.9800 . ?
C3_11 C4_11 1.525(7) . ?
C3_11 H6A_11 0.9900 . ?
C3_11 H6AB_11 0.9900 . ?
C4_11 H7A_11 0.9800 . ?
C4_11 H7B_11 0.9800 . ?
C4_11 H7C_11 0.9800 . ?
O1_2 C3_2 1.371(6) . ?
O1_2 C1_2 1.389(6) . ?
C1_2 C2_2 1.519(6) . ?
C1_2 H9A_2 0.9900 . ?
C1_2 H9AB_2 0.9900 . ?
C2_2 H10A_2 0.9800 . ?
C2_2 H10B_2 0.9800 . ?
C2_2 H10C_2 0.9800 . ?
C3_2 C4_2 1.524(6) . ?
C3_2 H11A_2 0.9900 . ?
C3_2 H11B_2 0.9900 . ?
C4_2 H12A_2 0.9800 . ?
C4_2 H12B_2 0.9800 . ?
C4_2 H12C_2 0.9800 . ?
O1_21 C3_21 1.383(7) . ?
O1_21 C1_21 1.400(6) . ?
C1_21 C2_21 1.540(7) . ?
C1_21 H9A_21 0.9900 . ?
C1_21 H9AB_21 0.9900 . ?
C2_21 H10A_21 0.9800 . ?
C2_21 H10B_21 0.9800 . ?
C2_21 H10C_21 0.9800 . ?
C3_21 C4_21 1.545(7) . ?
C3_21 H11A_21 0.9900 . ?
C3_21 H11B_21 0.9900 . ?
C4_21 H12A_21 0.9800 . ?
C4_21 H12B_21 0.9800 . ?
C4_21 H12C_21 0.9800 . ?

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
N2 N1 C8 111.6(3) . . ?
N2 N1 B1 121.3(2) . . ?
C8 N1 B1 126.6(3) . . ?
N2 C1 C2 126.3(3) . . ?
N2 C1 H1 116.8 . . ?
C2 C1 H1 116.8 . . ?
O1_2 Li1 O1_1 116.5(4) . . ?
O1_11 Li1 O1_21 102.2(6) . . ?
O1_11 Li1 N2 127.6(5) . . ?
O1_2 Li1 N2 121.2(4) . . ?
O1_1 Li1 N2 116.0(4) . . ?
O1_21 Li1 N2 126.5(5) . . ?
O1_11 Li1 C15 114.1(5) . . ?
O1_2 Li1 C15 116.7(4) . . ?
O1_1 Li1 C15 106.2(3) . . ?
O1_21 Li1 C15 109.1(4) . . ?
N2 Li1 C15 70.4(2) . . ?
O1_11 Li1 C1_11 26.8(4) . . ?
O1_21 Li1 C1_11 89.1(5) . . ?
N2 Li1 C1_11 144.3(4) . . ?
C15 Li1 C1_11 97.5(4) . . ?
N1 B1 C3 105.0(2) . . ?
N1 B1 C9 110.5(3) . . ?
C3 B1 C9 107.5(3) . . ?
N1 B1 C10 111.2(3) . . ?
C3 B1 C10 110.3(3) . . ?
C9 B1 C10 112.1(3) . . ?
C1 N2 N1 118.0(3) . . ?
C1 N2 Li1 126.2(3) . . ?
N1 N2 Li1 114.8(3) . . ?
C7 C2 C3 121.9(3) . . ?
C7 C2 C1 119.8(3) . . ?
C3 C2 C1 118.1(3) . . ?
C4 C3 C2 116.3(3) . . ?
C4 C3 B1 125.8(3) . . ?
C2 C3 B1 117.8(3) . . ?
C5 C4 C3 122.4(3) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C5 C6 C7 119.2(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C12 C11 C8 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C8 C11 H11 120.2 . . ?
C25 C10 C21 116.0(3) . . ?
C25 C10 B1 123.3(3) . . ?
C21 C10 B1 120.8(3) . . ?
C11 C8 N1 120.7(3) . . ?
C11 C8 C15 118.7(3) . . ?
N1 C8 C15 120.6(3) . . ?
C20 C9 C16 116.1(3) . . ?
C20 C9 B1 123.6(3) . . ?
C16 C9 B1 120.3(3) . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C11 C12 C13 121.6(4) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 119.3(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.1(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C8 120.6(4) . . ?
C14 C15 Li1 122.1(3) . . ?
C8 C15 Li1 83.8(3) . . ?
C14 C15 H15 119.7 . . ?
C8 C15 H15 119.7 . . ?
Li1 C15 H15 64.7 . . ?
C17 C16 C9 122.6(4) . . ?
C17 C16 H16 118.7 . . ?
C9 C16 H16 118.7 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 119.4(4) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C9 121.9(3) . . ?
C19 C20 H20 119.0 . . ?
C9 C20 H20 119.0 . . ?
C22 C21 C10 121.9(3) . . ?
C22 C21 H21 119.1 . . ?
C10 C21 H21 119.1 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C10 C25 C24 122.5(3) . . ?
C10 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C1_1 O1_1 C3_1 112.4(6) . . ?
C1_1 O1_1 Li1 120.9(5) . . ?
C3_1 O1_1 Li1 126.8(5) . . ?
O1_1 C1_1 C2_1 111.1(5) . . ?
O1_1 C1_1 H4A_1 109.4 . . ?
C2_1 C1_1 H4A_1 109.4 . . ?
O1_1 C1_1 H4AB_1 109.4 . . ?
C2_1 C1_1 H4AB_1 109.4 . . ?
H4A_1 C1_1 H4AB_1 108.0 . . ?
C1_1 C2_1 H5A_1 109.5 . . ?
C1_1 C2_1 H5B_1 109.5 . . ?
H5A_1 C2_1 H5B_1 109.5 . . ?
C1_1 C2_1 H5C_1 109.5 . . ?
H5A_1 C2_1 H5C_1 109.5 . . ?
H5B_1 C2_1 H5C_1 109.5 . . ?
O1_1 C3_1 C4_1 108.8(4) . . ?
O1_1 C3_1 H6A_1 109.9 . . ?
C4_1 C3_1 H6A_1 109.9 . . ?
O1_1 C3_1 H6AB_1 109.9 . . ?
C4_1 C3_1 H6AB_1 109.9 . . ?
H6A_1 C3_1 H6AB_1 108.3 . . ?
C3_1 C4_1 H7A_1 109.5 . . ?
C3_1 C4_1 H7B_1 109.5 . . ?
H7A_1 C4_1 H7B_1 109.5 . . ?
C3_1 C4_1 H7C_1 109.5 . . ?
H7A_1 C4_1 H7C_1 109.5 . . ?
H7B_1 C4_1 H7C_1 109.5 . . ?
C1_11 O1_11 C3_11 114.6(14) . . ?
C1_11 O1_11 Li1 115.0(11) . . ?
C3_11 O1_11 Li1 130.4(10) . . ?
O1_11 C1_11 C2_11 110.8(7) . . ?
O1_11 C1_11 Li1 38.3(8) . . ?
C2_11 C1_11 Li1 120.0(10) . . ?
O1_11 C1_11 H4A_11 109.5 . . ?
C2_11 C1_11 H4A_11 109.5 . . ?
Li1 C1_11 H4A_11 71.6 . . ?
O1_11 C1_11 H4AB_11 109.5 . . ?
C2_11 C1_11 H4AB_11 109.5 . . ?
Li1 C1_11 H4AB_11 127.7 . . ?
H4A_11 C1_11 H4AB_11 108.1 . . ?
C1_11 C2_11 H5A_11 109.5 . . ?
C1_11 C2_11 H5B_11 109.5 . . ?
H5A_11 C2_11 H5B_11 109.5 . . ?
C1_11 C2_11 H5C_11 109.5 . . ?
H5A_11 C2_11 H5C_11 109.5 . . ?
H5B_11 C2_11 H5C_11 109.5 . . ?
O1_11 C3_11 C4_11 110.3(7) . . ?
O1_11 C3_11 H6A_11 109.6 . . ?
C4_11 C3_11 H6A_11 109.6 . . ?
O1_11 C3_11 H6AB_11 109.6 . . ?
C4_11 C3_11 H6AB_11 109.6 . . ?
H6A_11 C3_11 H6AB_11 108.1 . . ?
C3_11 C4_11 H7A_11 109.5 . . ?
C3_11 C4_11 H7B_11 109.5 . . ?
H7A_11 C4_11 H7B_11 109.5 . . ?
C3_11 C4_11 H7C_11 109.5 . . ?
H7A_11 C4_11 H7C_11 109.5 . . ?
H7B_11 C4_11 H7C_11 109.5 . . ?
C3_2 O1_2 C1_2 97.9(9) . . ?
C3_2 O1_2 Li1 124.9(6) . . ?
C1_2 O1_2 Li1 123.4(7) . . ?
O1_2 C1_2 C2_2 112.1(6) . . ?
O1_2 C1_2 H9A_2 109.2 . . ?
C2_2 C1_2 H9A_2 109.2 . . ?
O1_2 C1_2 H9AB_2 109.2 . . ?
C2_2 C1_2 H9AB_2 109.2 . . ?
H9A_2 C1_2 H9AB_2 107.9 . . ?
C1_2 C2_2 H10A_2 109.5 . . ?
C1_2 C2_2 H10B_2 109.5 . . ?
H10A_2 C2_2 H10B_2 109.5 . . ?
C1_2 C2_2 H10C_2 109.5 . . ?
H10A_2 C2_2 H10C_2 109.5 . . ?
H10B_2 C2_2 H10C_2 109.5 . . ?
O1_2 C3_2 C4_2 110.9(6) . . ?
O1_2 C3_2 H11A_2 109.5 . . ?
C4_2 C3_2 H11A_2 109.5 . . ?
O1_2 C3_2 H11B_2 109.5 . . ?
C4_2 C3_2 H11B_2 109.5 . . ?
H11A_2 C3_2 H11B_2 108.1 . . ?
C3_2 C4_2 H12A_2 109.5 . . ?
C3_2 C4_2 H12B_2 109.5 . . ?
H12A_2 C4_2 H12B_2 109.5 . . ?
C3_2 C4_2 H12C_2 109.5 . . ?
H12A_2 C4_2 H12C_2 109.5 . . ?
H12B_2 C4_2 H12C_2 109.5 . . ?
C3_21 O1_21 C1_21 105.3(11) . . ?
C3_21 O1_21 Li1 129.2(8) . . ?
C1_21 O1_21 Li1 119.5(8) . . ?
O1_21 C1_21 C2_21 109.2(6) . . ?
O1_21 C1_21 H9A_21 109.8 . . ?
C2_21 C1_21 H9A_21 109.8 . . ?
O1_21 C1_21 H9AB_21 109.8 . . ?
C2_21 C1_21 H9AB_21 109.8 . . ?
H9A_21 C1_21 H9AB_21 108.3 . . ?
C1_21 C2_21 H10A_21 109.5 . . ?
C1_21 C2_21 H10B_21 109.5 . . ?
H10A_21 C2_21 H10B_21 109.5 . . ?
C1_21 C2_21 H10C_21 109.5 . . ?
H10A_21 C2_21 H10C_21 109.5 . . ?
H10B_21 C2_21 H10C_21 109.5 . . ?
O1_21 C3_21 C4_21 108.0(6) . . ?
O1_21 C3_21 H11A_21 110.1 . . ?
C4_21 C3_21 H11A_21 110.1 . . ?
O1_21 C3_21 H11B_21 110.1 . . ?
C4_21 C3_21 H11B_21 110.1 . . ?
H11A_21 C3_21 H11B_21 108.4 . . ?
C3_21 C4_21 H12A_21 109.5 . . ?
C3_21 C4_21 H12B_21 109.5 . . ?
H12A_21 C4_21 H12B_21 109.5 . . ?
C3_21 C4_21 H12C_21 109.5 . . ?
H12A_21 C4_21 H12C_21 109.5 . . ?
H12B_21 C4_21 H12C_21 109.5 . . ?

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
N2 N1 B1 C3 -40.6(4) . . . . ?
C8 N1 B1 C3 148.5(3) . . . . ?
N2 N1 B1 C9 75.1(4) . . . . ?
C8 N1 B1 C9 -95.8(4) . . . . ?
N2 N1 B1 C10 -159.8(3) . . . . ?
C8 N1 B1 C10 29.3(4) . . . . ?
C2 C1 N2 N1 8.4(5) . . . . ?
C2 C1 N2 Li1 176.8(4) . . . . ?
C8 N1 N2 C1 -165.7(3) . . . . ?
B1 N1 N2 C1 22.2(4) . . . . ?
C8 N1 N2 Li1 24.6(4) . . . . ?
B1 N1 N2 Li1 -147.5(3) . . . . ?
N2 C1 C2 C7 161.7(4) . . . . ?
N2 C1 C2 C3 -13.7(5) . . . . ?
C7 C2 C3 C4 -3.1(5) . . . . ?
C1 C2 C3 C4 172.2(3) . . . . ?
C7 C2 C3 B1 173.6(3) . . . . ?
C1 C2 C3 B1 -11.1(5) . . . . ?
N1 B1 C3 C4 -150.2(3) . . . . ?
C9 B1 C3 C4 92.2(4) . . . . ?
C10 B1 C3 C4 -30.3(5) . . . . ?
N1 B1 C3 C2 33.5(4) . . . . ?
C9 B1 C3 C2 -84.2(3) . . . . ?
C10 B1 C3 C2 153.3(3) . . . . ?
C2 C3 C4 C5 2.6(6) . . . . ?
B1 C3 C4 C5 -173.8(4) . . . . ?
N1 B1 C10 C25 -126.0(3) . . . . ?
C3 B1 C10 C25 118.0(4) . . . . ?
C9 B1 C10 C25 -1.7(5) . . . . ?
N1 B1 C10 C21 54.7(4) . . . . ?
C3 B1 C10 C21 -61.3(4) . . . . ?
C9 B1 C10 C21 178.9(3) . . . . ?
C12 C11 C8 N1 -178.9(3) . . . . ?
C12 C11 C8 C15 -0.2(5) . . . . ?
N2 N1 C8 C11 -144.8(3) . . . . ?
B1 N1 C8 C11 26.8(5) . . . . ?
N2 N1 C8 C15 36.5(4) . . . . ?
B1 N1 C8 C15 -151.9(3) . . . . ?
N1 B1 C9 C20 15.1(4) . . . . ?
C3 B1 C9 C20 129.1(3) . . . . ?
C10 B1 C9 C20 -109.6(3) . . . . ?
N1 B1 C9 C16 -166.1(3) . . . . ?
C3 B1 C9 C16 -52.1(4) . . . . ?
C10 B1 C9 C16 69.3(4) . . . . ?
C5 C6 C7 C2 -0.4(7) . . . . ?
C3 C2 C7 C6 2.1(6) . . . . ?
C1 C2 C7 C6 -173.1(4) . . . . ?
C3 C4 C5 C6 -1.1(7) . . . . ?
C7 C6 C5 C4 -0.1(7) . . . . ?
C8 C11 C12 C13 0.4(7) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C12 C13 C14 C15 1.6(7) . . . . ?
C13 C14 C15 C8 -1.5(6) . . . . ?
C13 C14 C15 Li1 -104.3(5) . . . . ?
C11 C8 C15 C14 0.7(5) . . . . ?
N1 C8 C15 C14 179.5(3) . . . . ?
C11 C8 C15 Li1 124.6(3) . . . . ?
N1 C8 C15 Li1 -56.7(3) . . . . ?
C20 C9 C16 C17 1.0(5) . . . . ?
B1 C9 C16 C17 -177.9(3) . . . . ?
C9 C16 C17 C18 -0.9(6) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C17 C18 C19 C20 1.4(6) . . . . ?
C18 C19 C20 C9 -1.2(5) . . . . ?
C16 C9 C20 C19 0.0(5) . . . . ?
B1 C9 C20 C19 178.9(3) . . . . ?
C25 C10 C21 C22 0.4(5) . . . . ?
B1 C10 C21 C22 179.8(3) . . . . ?
C10 C21 C22 C23 0.3(6) . . . . ?
C21 C22 C23 C24 -1.1(6) . . . . ?
C22 C23 C24 C25 1.2(6) . . . . ?
C21 C10 C25 C24 -0.3(5) . . . . ?
B1 C10 C25 C24 -179.7(3) . . . . ?
C23 C24 C25 C10 -0.5(6) . . . . ?
C3_1 O1_1 C1_1 C2_1 87.5(9) . . . . ?
Li1 O1_1 C1_1 C2_1 -92.2(7) . . . . ?
C1_1 O1_1 C3_1 C4_1 178.7(9) . . . . ?
Li1 O1_1 C3_1 C4_1 -1.7(14) . . . . ?
C3_11 O1_11 C1_11 C2_11 -70(2) . . . . ?
Li1 O1_11 C1_11 C2_11 112.4(14) . . . . ?
C3_11 O1_11 C1_11 Li1 177(2) . . . . ?
C1_11 O1_11 C3_11 C4_11 -163(2) . . . . ?
Li1 O1_11 C3_11 C4_11 14(4) . . . . ?
C3_2 O1_2 C1_2 C2_2 99.8(10) . . . . ?
Li1 O1_2 C1_2 C2_2 -118.7(10) . . . . ?
C1_2 O1_2 C3_2 C4_2 -102.1(10) . . . . ?
Li1 O1_2 C3_2 C4_2 117.3(9) . . . . ?
C3_21 O1_21 C1_21 C2_21 -92.1(14) . . . . ?
Li1 O1_21 C1_21 C2_21 112.9(12) . . . . ?
C1_21 O1_21 C3_21 C4_21 143.8(12) . . . . ?
Li1 O1_21 C3_21 C4_21 -64.5(16) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-Dur
_database_code_depnum_ccdc_archive 'CCDC 2394197'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.4c (K.Radacki, 2005-23)'
_audit_creation_date             2023-05-08
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C23 H23 B N2'
_chemical_formula_sum            'C23 H23 B N2'
_chemical_formula_weight         338.24
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   10.59790(10)
_cell_length_b                   15.3284(2)
_cell_length_c                   11.92880(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.0560(10)
_cell_angle_gamma                90
_cell_volume                     1879.80(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    24495
_cell_measurement_theta_min      2.8710
_cell_measurement_theta_max      74.0340

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.1162
0 0 1 0.1195
2 0 1 0.0849
-2 0 -1 0.0941
-1 1 1 0.1209
-1 -1 -2 0.0956
1 -1 -1 0.0984
1 1 2 0.0947
1 2 2 0.0853
-1 1 0 0.1057
1 -1 0 0.0726
0 2 1 0.0916
0 -2 -1 0.0875
1 1 1 0.0714
-1 -1 -1 0.0862
1 -2 0 0.0678
-1 2 0 0.1101
0 1 0 0.0954
0 -1 0 0.0725
-1 -2 0 0.0575
1 2 0 0.0476
-1 1 -1 0.1152
1 -1 1 0.0824
-1 -1 0 0.0755
1 1 0 0.0599

_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.944
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     59.00  84.00   0.50    0.05    --   46.00  52.00 162.32   50
  2  ω     62.00  87.00   0.50    0.05    --   46.00  52.00  14.20   50
  3  ω     47.00  72.00   0.50    0.05    --   34.00  52.00 -35.96   50
  4  ω     53.00  84.00   0.50    0.05    --   38.00  50.00 -10.25   62
  5  ω    102.00 128.00   0.50    0.05    --   80.79  45.00   8.60   52
  6  ω     24.00  90.00   0.50    0.05    --   58.57-132.00 -42.00  132
  7  ω     30.00 103.00   0.50    0.05    --   76.90-132.00 -42.00  146
  8  ω     25.00 102.00   0.50    0.05    --   71.34-132.00 -42.00  154
  9  ω     46.00  71.00   0.50    0.05    --   84.69-132.00 -42.00   50
 10  ω     35.00  65.00   0.50    0.05    --   80.79-114.00-177.13   60
 11  ω     29.00  94.00   0.50    0.05    --   58.57-139.00 142.00  130
 12  ω     31.00 109.00   0.50    0.05    --   76.90-139.00 142.00  156
 13  ω     39.00 108.00   0.50    0.05    --   84.69-139.00 142.00  138
 14  ω     49.00  92.00   0.50    0.05    --   80.79-100.00 139.10   86
 15  ω     45.00  92.00   0.50    0.05    --   84.69 -95.00  30.00   94
 16  ω     48.00  92.00   0.50    0.05    --   84.69 -95.00   0.00   88
 17  ω     34.00  81.00   0.50    0.05    --   76.90 -95.00 -30.00   94
 18  ω     52.00  91.00   0.50    0.05    --   84.69 -95.00 -60.00   78
 19  ω     42.00  91.00   0.50    0.05    --   84.69 -95.00-120.00   98
 20  ω     56.00  92.00   0.50    0.05    --   84.69 -95.00-180.00   72
 21  ω     42.00  91.00   0.50    0.05    --   84.69 -95.00 -90.00   98
 22  ω     45.00  90.00   0.50    0.05    --   84.69 -95.00  60.00   90
 23  ω     58.00  92.00   0.50    0.05    --   84.69 -95.00  90.00   68
 24  ω     96.00 128.00   0.50    0.05    --   80.79  49.00-121.10   64
 25  ω    -96.00 -23.00   0.50    0.05    --  -60.16 139.00-157.00  146
 26  ω   -105.00 -24.00   0.50    0.05    --  -69.76 139.00-157.00  162
 27  ω   -108.00 -30.00   0.50    0.05    --  -76.35 139.00-157.00  156
 28  ω    -97.00 -35.00   0.50    0.05    --  -79.50 116.00 -14.52  124
 29  ω   -101.00 -23.00   0.50    0.05    --  -69.76 132.00  27.00  156
 30  ω    -91.00 -18.00   0.50    0.05    --  -60.16 132.00  27.00  146
 31  ω   -102.00 -29.00   0.50    0.05    --  -76.35 132.00  27.00  146
 32  ω    -92.00 -32.00   0.50    0.05    --  -76.35 112.00 150.00  120
 33  ω   -123.00 -92.00   0.50    0.05    --  -79.50 -63.00 101.99   62
 34  ω   -122.00 -90.00   0.50    0.05    --  -79.50 -62.00 122.35   64
 35  ω   -115.00 -86.00   0.50    0.05    --  -70.00 -59.00  32.46   58
 36  ω   -120.00 -92.00   0.50    0.05    --  -74.00 -55.00   1.44   56
 37  ω   -125.00-100.00   0.50    0.05    --  -79.50 -61.00   0.89   50
 38  ω   -126.00 -94.00   0.50    0.05    --  -79.50 -53.00 125.77   64
 39  ω   -121.00 -95.00   0.50    0.05    --  -74.00 -55.00 137.71   52
 40  ω   -125.00 -93.00   0.50    0.05    --  -79.50 -52.00  48.45   64
 41  ω   -120.00 -87.00   0.50    0.05    --  -74.00 -56.00 -67.92   66
 42  ω   -106.00 -81.00   0.50    0.05    --  -58.00 -51.00 -50.48   50
 43  ω   -116.00 -90.00   0.50    0.05    --  -70.00 -56.00-139.78   52
 44  ω   -125.00 -93.00   0.50    0.05    --  -79.50 -61.00-168.52   64
 45  ω   -128.00 -98.00   0.50    0.05    --  -79.50 -51.00 -38.38   60
 46  ω   -101.00 -72.00   0.50    0.05    --  -58.00 -48.00-153.65   58
 47  ω   -107.00 -73.00   0.50    0.05    --  -58.00 -49.00  51.78   68
 48  ω   -130.00-105.00   0.50    0.05    --  -79.50 -40.00 -78.97   50
 49  ω   -108.00 -80.00   0.50    0.05    --  -66.00 -44.00 136.09   56
 50  ω   -111.00 -76.00   0.50    0.05    --  -62.00 -48.00 174.39   70
 51  ω   -128.00-103.00   0.50    0.05    --  -79.50 -51.00 169.29   50
 52  ω   -125.00 -95.00   0.50    0.05    --  -79.50-121.00  86.13   60
 53  ω   -125.00 -99.00   0.50    0.05    --  -79.50-120.00-155.97   52
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0055391000
_diffrn_orient_matrix_UB_12      0.0996140000
_diffrn_orient_matrix_UB_13      -0.0155700000
_diffrn_orient_matrix_UB_21      0.0678903000
_diffrn_orient_matrix_UB_22      -0.0132356000
_diffrn_orient_matrix_UB_23      -0.0992273000
_diffrn_orient_matrix_UB_31      -0.1334556000
_diffrn_orient_matrix_UB_32      -0.0027028000
_diffrn_orient_matrix_UB_33      -0.0873336000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            35040
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.301
_diffrn_reflns_theta_max         75.036
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3711
_reflns_number_gt                3470
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0526P)²+0.7372P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3711
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 0.85543(9) 0.34598(6) 0.34553(8) 0.0213(2) Uani 1 1 d . . . . .
C1 C 1.01211(11) 0.44348(8) 0.32363(10) 0.0256(3) Uani 1 1 d . . . . .
H1 H 1.101464 0.457090 0.332584 0.031 Uiso 1 1 calc R U . . .
B1 B 0.74980(12) 0.40508(8) 0.30675(10) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.98614(9) 0.36608(6) 0.35587(9) 0.0250(2) Uani 1 1 d . . . . .
C2 C 0.92036(11) 0.51108(8) 0.27576(9) 0.0232(2) Uani 1 1 d . . . . .
C3 C 0.78723(11) 0.49382(7) 0.26394(9) 0.0211(2) Uani 1 1 d . . . . .
C7 C 0.96195(12) 0.59163(8) 0.24097(10) 0.0277(3) Uani 1 1 d . . . . .
H7 H 1.051985 0.602493 0.249141 0.033 Uiso 1 1 calc R U . . .
C4 C 0.69739(11) 0.55924(7) 0.21593(9) 0.0233(2) Uani 1 1 d . . . . .
H4 H 0.607041 0.548986 0.206734 0.028 Uiso 1 1 calc R U . . .
C6 C 0.87156(12) 0.65460(8) 0.19505(10) 0.0292(3) Uani 1 1 d . . . . .
H6 H 0.899352 0.709285 0.172204 0.035 Uiso 1 1 calc R U . . .
C5 C 0.73863(12) 0.63827(8) 0.18190(10) 0.0269(3) Uani 1 1 d . . . . .
H5 H 0.676588 0.681735 0.149441 0.032 Uiso 1 1 calc R U . . .
C8 C 0.84040(11) 0.25963(7) 0.38791(9) 0.0223(2) Uani 1 1 d . . . . .
C9 C 0.60776(10) 0.38411(7) 0.31885(9) 0.0204(2) Uani 1 1 d . . . . .
C13 C 0.90289(13) 0.14873(9) 0.53264(11) 0.0324(3) Uani 1 1 d . . . . .
H13 H 0.957136 0.129456 0.603868 0.039 Uiso 1 1 calc R U . . .
C10 C 0.74515(11) 0.20455(8) 0.32490(10) 0.0244(2) Uani 1 1 d . . . . .
H10 H 0.691101 0.223585 0.253448 0.029 Uiso 1 1 calc R U . . .
C12 C 0.80784(13) 0.09361(8) 0.47031(11) 0.0310(3) Uani 1 1 d . . . . .
H12 H 0.796872 0.036920 0.498706 0.037 Uiso 1 1 calc R U . . .
C11 C 0.72880(12) 0.12159(8) 0.36625(11) 0.0282(3) Uani 1 1 d . . . . .
H11 H 0.663418 0.084047 0.323174 0.034 Uiso 1 1 calc R U . . .
C15 C 0.50475(11) 0.36955(7) 0.22150(10) 0.0227(2) Uani 1 1 d . . . . .
C14 C 0.91986(12) 0.23168(8) 0.49242(10) 0.0276(3) Uani 1 1 d . . . . .
H14 H 0.985168 0.269128 0.535817 0.033 Uiso 1 1 calc R U . . .
C16 C 0.37823(11) 0.35610(7) 0.23559(11) 0.0259(3) Uani 1 1 d . . . . .
C17 C 0.35811(11) 0.35858(7) 0.34680(11) 0.0275(3) Uani 1 1 d . . . . .
H17 H 0.272655 0.349321 0.356239 0.033 Uiso 1 1 calc R U . . .
C20 C 0.69379(12) 0.40489(8) 0.53500(10) 0.0280(3) Uani 1 1 d . . . . .
H20A H 0.766466 0.431972 0.510503 0.042 Uiso 1 1 calc R U . . .
H20B H 0.722788 0.349964 0.575081 0.042 Uiso 1 1 calc R U . . .
H20C H 0.663231 0.444421 0.587356 0.042 Uiso 1 1 calc R U . . .
C19 C 0.58406(11) 0.38683(7) 0.43019(10) 0.0223(2) Uani 1 1 d . . . . .
C18 C 0.45761(12) 0.37399(7) 0.44415(11) 0.0254(3) Uani 1 1 d . . . . .
C21 C 0.42799(13) 0.37861(8) 0.56156(11) 0.0327(3) Uani 1 1 d . . . . .
H21A H 0.334930 0.368427 0.553563 0.049 Uiso 1 1 calc R U . . .
H21B H 0.451479 0.436430 0.595237 0.049 Uiso 1 1 calc R U . . .
H21C H 0.478332 0.333954 0.612107 0.049 Uiso 1 1 calc R U . . .
C22 C 0.26510(12) 0.33899(9) 0.13392(12) 0.0349(3) Uani 1 1 d . . . . .
H22A H 0.251872 0.389600 0.082171 0.052 Uiso 1 1 calc R U . . .
H22B H 0.186412 0.328861 0.161448 0.052 Uiso 1 1 calc R U . . .
H22C H 0.283441 0.287394 0.092017 0.052 Uiso 1 1 calc R U . . .
C23 C 0.52916(12) 0.36743(8) 0.10174(10) 0.0279(3) Uani 1 1 d . . . . .
H23A H 0.498044 0.311934 0.064293 0.042 Uiso 1 1 calc R U . . .
H23B H 0.622615 0.373235 0.107521 0.042 Uiso 1 1 calc R U . . .
H23C H 0.482642 0.415747 0.055831 0.042 Uiso 1 1 calc R U . . .


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 N2 1.3951(13) . ?
N1 B1 1.4270(15) . ?
N1 C8 1.4394(14) . ?
C1 N2 1.2971(16) . ?
C1 C2 1.4407(16) . ?
B1 C3 1.5384(16) . ?
B1 C9 1.5798(16) . ?
C2 C7 1.4070(16) . ?
C2 C3 1.4085(16) . ?
C3 C4 1.4054(16) . ?
C7 C6 1.3765(18) . ?
C4 C5 1.3817(16) . ?
C6 C5 1.4017(17) . ?
C8 C10 1.3887(16) . ?
C8 C14 1.3918(16) . ?
C9 C15 1.4051(16) . ?
C9 C19 1.4110(15) . ?
C13 C12 1.3848(19) . ?
C13 C14 1.3860(18) . ?
C10 C11 1.3899(17) . ?
C12 C11 1.3861(18) . ?
C15 C16 1.4065(16) . ?
C15 C23 1.5127(16) . ?
C16 C17 1.3943(18) . ?
C16 C22 1.5070(17) . ?
C17 C18 1.3862(18) . ?
C20 C19 1.5119(16) . ?
C19 C18 1.4039(16) . ?
C18 C21 1.5095(16) . ?

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
N2 N1 B1 124.92(9) . . ?
N2 N1 C8 111.36(9) . . ?
B1 N1 C8 123.55(9) . . ?
N2 C1 C2 127.16(11) . . ?
N1 B1 C3 115.07(10) . . ?
N1 B1 C9 122.08(10) . . ?
C3 B1 C9 122.58(10) . . ?
C1 N2 N1 116.96(10) . . ?
C7 C2 C3 120.88(11) . . ?
C7 C2 C1 121.23(10) . . ?
C3 C2 C1 117.89(10) . . ?
C4 C3 C2 118.02(10) . . ?
C4 C3 B1 124.22(10) . . ?
C2 C3 B1 117.75(10) . . ?
C6 C7 C2 119.68(11) . . ?
C5 C4 C3 120.92(11) . . ?
C7 C6 C5 120.17(11) . . ?
C4 C5 C6 120.32(11) . . ?
C10 C8 C14 119.99(11) . . ?
C10 C8 N1 119.79(10) . . ?
C14 C8 N1 120.21(10) . . ?
C15 C9 C19 120.16(10) . . ?
C15 C9 B1 121.54(10) . . ?
C19 C9 B1 118.12(10) . . ?
C12 C13 C14 120.83(12) . . ?
C8 C10 C11 120.07(11) . . ?
C13 C12 C11 119.64(11) . . ?
C12 C11 C10 120.04(11) . . ?
C9 C15 C16 119.76(10) . . ?
C9 C15 C23 120.48(10) . . ?
C16 C15 C23 119.76(10) . . ?
C13 C14 C8 119.43(11) . . ?
C17 C16 C15 118.71(11) . . ?
C17 C16 C22 119.66(11) . . ?
C15 C16 C22 121.64(11) . . ?
C18 C17 C16 122.73(11) . . ?
C18 C19 C9 120.05(11) . . ?
C18 C19 C20 119.49(10) . . ?
C9 C19 C20 120.45(10) . . ?
C17 C18 C19 118.58(11) . . ?
C17 C18 C21 119.87(11) . . ?
C19 C18 C21 121.54(11) . . ?

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
N2 N1 B1 C3 5.72(15) . . . . ?
C8 N1 B1 C3 -179.50(9) . . . . ?
N2 N1 B1 C9 -168.43(10) . . . . ?
C8 N1 B1 C9 6.35(16) . . . . ?
C2 C1 N2 N1 -1.37(17) . . . . ?
B1 N1 N2 C1 -2.61(15) . . . . ?
C8 N1 N2 C1 -177.94(10) . . . . ?
N2 C1 C2 C7 -178.00(11) . . . . ?
N2 C1 C2 C3 1.52(18) . . . . ?
C7 C2 C3 C4 0.30(16) . . . . ?
C1 C2 C3 C4 -179.22(10) . . . . ?
C7 C2 C3 B1 -178.52(10) . . . . ?
C1 C2 C3 B1 1.96(15) . . . . ?
N1 B1 C3 C4 176.10(10) . . . . ?
C9 B1 C3 C4 -9.78(16) . . . . ?
N1 B1 C3 C2 -5.16(14) . . . . ?
C9 B1 C3 C2 168.96(10) . . . . ?
C3 C2 C7 C6 0.18(17) . . . . ?
C1 C2 C7 C6 179.69(11) . . . . ?
C2 C3 C4 C5 -0.32(16) . . . . ?
B1 C3 C4 C5 178.42(10) . . . . ?
C2 C7 C6 C5 -0.65(18) . . . . ?
C3 C4 C5 C6 -0.14(17) . . . . ?
C7 C6 C5 C4 0.63(18) . . . . ?
N2 N1 C8 C10 -135.54(10) . . . . ?
B1 N1 C8 C10 49.06(15) . . . . ?
N2 N1 C8 C14 45.28(13) . . . . ?
B1 N1 C8 C14 -130.12(12) . . . . ?
N1 B1 C9 C15 -112.82(12) . . . . ?
C3 B1 C9 C15 73.47(14) . . . . ?
N1 B1 C9 C19 71.93(14) . . . . ?
C3 B1 C9 C19 -101.78(12) . . . . ?
C14 C8 C10 C11 0.19(17) . . . . ?
N1 C8 C10 C11 -178.99(10) . . . . ?
C14 C13 C12 C11 0.13(19) . . . . ?
C13 C12 C11 C10 0.04(18) . . . . ?
C8 C10 C11 C12 -0.20(17) . . . . ?
C19 C9 C15 C16 -1.15(16) . . . . ?
B1 C9 C15 C16 -176.30(10) . . . . ?
C19 C9 C15 C23 179.39(10) . . . . ?
B1 C9 C15 C23 4.24(16) . . . . ?
C12 C13 C14 C8 -0.14(19) . . . . ?
C10 C8 C14 C13 -0.02(17) . . . . ?
N1 C8 C14 C13 179.16(10) . . . . ?
C9 C15 C16 C17 0.70(16) . . . . ?
C23 C15 C16 C17 -179.84(10) . . . . ?
C9 C15 C16 C22 -179.13(10) . . . . ?
C23 C15 C16 C22 0.32(17) . . . . ?
C15 C16 C17 C18 0.18(17) . . . . ?
C22 C16 C17 C18 -179.98(11) . . . . ?
C15 C9 C19 C18 0.73(16) . . . . ?
B1 C9 C19 C18 176.04(10) . . . . ?
C15 C9 C19 C20 -178.35(10) . . . . ?
B1 C9 C19 C20 -3.03(15) . . . . ?
C16 C17 C18 C19 -0.60(17) . . . . ?
C16 C17 C18 C21 178.06(11) . . . . ?
C9 C19 C18 C17 0.14(16) . . . . ?
C20 C19 C18 C17 179.23(10) . . . . ?
C9 C19 C18 C21 -178.50(10) . . . . ?
C20 C19 C18 C21 0.59(16) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-Ph
_database_code_depnum_ccdc_archive 'CCDC 2394203'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.4c (K.Radacki, 2005-23)'
_audit_creation_date             2023-05-08
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C19 H15 B N2'
_chemical_formula_sum            'C19 H15 B N2'
_chemical_formula_weight         282.14
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'


_cell_length_a                   11.2275(2)
_cell_length_b                   9.6336(2)
_cell_length_c                   13.9575(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.194(2)
_cell_angle_gamma                90
_cell_volume                     1480.94(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8052
_cell_measurement_theta_min      5.5880
_cell_measurement_theta_max      73.8600

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 1 0.0448
1 2 0 0.0489
-1 -2 0 0.0427
-1 -1 -1 0.0579
-1 0 -1 0.0801
-1 -2 -1 0.0481
0 1 0 0.0527
1 -2 0 0.0411
-2 0 -1 0.0593
-2 1 0 0.0526
0 -2 -1 0.0436
0 2 1 0.0382
-1 1 1 0.0353
-2 1 1 0.0349
2 -1 -2 0.1000
-2 1 2 0.0374
-1 1 2 0.0288
1 -1 -2 0.0793
-1 -1 1 0.0449
0 0 1 0.0365
0 0 -1 0.1111

_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.956
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     39.00  93.00   0.50    0.21    --   84.69-112.00 120.00  108
  2  ω     32.00  92.00   0.50    0.21    --   76.90-112.00  30.00  120
  3  ω     32.00  92.00   0.50    0.21    --   76.90-112.00 -90.00  120
  4  ω     32.00  92.00   0.50    0.21    --   76.90-112.00-150.00  120
  5  ω     20.00  86.00   0.50    0.05    --   58.57-126.00-150.00  132
  6  ω     16.00  66.00   0.50    0.05    --   58.57 -95.00 -90.00  100
  7  ω     42.00  92.00   0.50    0.21    --   84.69 -95.00 -60.00  100
  8  ω     29.00  79.00   0.50    0.05    --   71.34 -95.00-150.00  100
  9  ω     16.00  66.00   0.50    0.05    --   58.57 -95.00  30.00  100
 10  ω     34.00  85.00   0.50    0.21    --   76.90 -95.00  60.00  102
 11  ω     16.00  66.00   0.50    0.05    --   58.57 -95.00 120.00  100
 12  ω     42.00  92.00   0.50    0.21    --   84.69 -95.00 150.00  100
 13  ω     48.00 135.00   0.50    0.21    --   84.69  15.00 -30.00  174
 14  ω     48.00 135.00   0.50    0.21    --   84.69  15.00 -90.00  174
 15  ω     48.00 135.00   0.50    0.21    --   84.69  15.00-180.00  174
 16  ω     38.00 109.00   0.50    0.05    --   58.57  15.00-120.00  142
 17  ω     48.00 135.00   0.50    0.21    --   84.69  15.00  60.00  174
 18  ω     38.00 109.00   0.50    0.05    --   58.57  15.00 150.00  142
 19  ω   -127.00 -40.00   0.50    0.21    --  -76.35 -15.00-120.00  174
 20  ω   -127.00 -40.00   0.50    0.21    --  -76.35 -15.00 -30.00  174
 21  ω   -127.00 -40.00   0.50    0.21    --  -76.35 -15.00  60.00  174
 22  ω   -127.00 -40.00   0.50    0.21    --  -76.35 -15.00 150.00  174
 23  ω    -92.00 -31.00   0.50    0.21    --  -76.35 112.00  90.00  122
 24  ω    -92.00 -63.00   0.50    0.21    --  -76.35 112.00   0.00   58
 25  ω    -97.00 -22.00   0.50    0.05    --  -69.76 126.00 -90.00  150
 26  ω    -92.00 -31.00   0.50    0.21    --  -76.35 112.00-120.00  122
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0970845000
_diffrn_orient_matrix_UB_12      -0.0333539000
_diffrn_orient_matrix_UB_13      -0.0609114000
_diffrn_orient_matrix_UB_21      -0.0636750000
_diffrn_orient_matrix_UB_22      0.0985086000
_diffrn_orient_matrix_UB_23      -0.0809499000
_diffrn_orient_matrix_UB_31      0.0781015000
_diffrn_orient_matrix_UB_32      0.1214581000
_diffrn_orient_matrix_UB_33      0.0488942000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            20170
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.615
_diffrn_reflns_theta_max         74.811
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2959
_reflns_number_gt                2529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0438P)²+0.6109P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 0.59225(10) 0.42953(12) 0.37375(9) 0.0246(3) Uani 1 1 d . . . . .
C1 C 0.43660(13) 0.29095(15) 0.29769(10) 0.0265(3) Uani 1 1 d . . . . .
H1 H 0.396432 0.203686 0.292205 0.032 Uiso 1 1 calc R U . . .
B1 B 0.55407(14) 0.54904(16) 0.31629(12) 0.0247(3) Uani 1 1 d . . . . .
N2 N 0.53484(11) 0.30040(12) 0.36384(9) 0.0271(3) Uani 1 1 d . . . . .
C2 C 0.38179(12) 0.39767(15) 0.23182(10) 0.0259(3) Uani 1 1 d . . . . .
C8 C 0.70032(12) 0.42427(14) 0.44868(10) 0.0247(3) Uani 1 1 d . . . . .
C9 C 0.62772(13) 0.68898(14) 0.33162(10) 0.0251(3) Uani 1 1 d . . . . .
C10 C 0.70616(13) 0.50043(15) 0.53374(10) 0.0275(3) Uani 1 1 d . . . . .
H10 H 0.638017 0.552675 0.544104 0.033 Uiso 1 1 calc R U . . .
C11 C 0.81263(13) 0.49955(15) 0.60362(11) 0.0296(3) Uani 1 1 d . . . . .
H11 H 0.817407 0.551688 0.662014 0.036 Uiso 1 1 calc R U . . .
C12 C 0.91183(13) 0.42321(16) 0.58872(11) 0.0304(3) Uani 1 1 d . . . . .
H12 H 0.984763 0.423884 0.636438 0.037 Uiso 1 1 calc R U . . .
C13 C 0.90466(14) 0.34548(16) 0.50381(11) 0.0308(3) Uani 1 1 d . . . . .
H13 H 0.972501 0.292371 0.493829 0.037 Uiso 1 1 calc R U . . .
C14 C 0.79898(13) 0.34544(15) 0.43397(11) 0.0278(3) Uani 1 1 d . . . . .
H14 H 0.793732 0.291825 0.376176 0.033 Uiso 1 1 calc R U . . .
C15 C 0.56816(14) 0.81603(15) 0.33777(11) 0.0295(3) Uani 1 1 d . . . . .
H15 H 0.482928 0.816225 0.334917 0.035 Uiso 1 1 calc R U . . .
C16 C 0.63047(14) 0.94118(15) 0.34789(11) 0.0316(3) Uani 1 1 d . . . . .
H16 H 0.587950 1.025482 0.352253 0.038 Uiso 1 1 calc R U . . .
C17 C 0.75494(14) 0.94330(15) 0.35166(11) 0.0313(3) Uani 1 1 d . . . . .
H17 H 0.797748 1.028912 0.358502 0.038 Uiso 1 1 calc R U . . .
C18 C 0.81652(13) 0.81971(15) 0.34537(10) 0.0287(3) Uani 1 1 d . . . . .
H18 H 0.901610 0.820564 0.347536 0.034 Uiso 1 1 calc R U . . .
C19 C 0.75370(13) 0.69510(15) 0.33594(10) 0.0259(3) Uani 1 1 d . . . . .
H19 H 0.797125 0.611250 0.332281 0.031 Uiso 1 1 calc R U . . .
C3 C 0.43834(12) 0.52924(14) 0.23729(10) 0.0255(3) Uani 1 1 d . . . . .
C4 C 0.38730(13) 0.63032(15) 0.16815(10) 0.0281(3) Uani 1 1 d . . . . .
H4 H 0.424827 0.718796 0.168894 0.034 Uiso 1 1 calc R U . . .
C7 C 0.27608(13) 0.37051(16) 0.16170(10) 0.0288(3) Uani 1 1 d . . . . .
H7 H 0.238434 0.281922 0.159206 0.035 Uiso 1 1 calc R U . . .
C6 C 0.22753(13) 0.47244(16) 0.09689(11) 0.0308(3) Uani 1 1 d . . . . .
H6 H 0.155593 0.454565 0.050186 0.037 Uiso 1 1 calc R U . . .
C5 C 0.28377(14) 0.60288(16) 0.09943(11) 0.0310(3) Uani 1 1 d . . . . .
H5 H 0.250554 0.672472 0.053762 0.037 Uiso 1 1 calc R U . . .


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 N2 1.3955(16) . ?
N1 B1 1.4210(19) . ?
N1 C8 1.4408(18) . ?
C1 N2 1.2969(18) . ?
C1 C2 1.436(2) . ?
B1 C3 1.544(2) . ?
B1 C9 1.574(2) . ?
C2 C7 1.4086(19) . ?
C2 C3 1.4131(19) . ?
C8 C10 1.386(2) . ?
C8 C14 1.391(2) . ?
C9 C19 1.405(2) . ?
C9 C15 1.4053(19) . ?
C10 C11 1.388(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.391(2) . ?
C13 C14 1.382(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.388(2) . ?
C18 C19 1.386(2) . ?
C3 C4 1.412(2) . ?
C4 C5 1.381(2) . ?
C7 C6 1.374(2) . ?
C6 C5 1.404(2) . ?

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
N2 N1 B1 125.69(12) . . ?
N2 N1 C8 110.38(11) . . ?
B1 N1 C8 123.88(12) . . ?
N2 C1 C2 127.24(13) . . ?
N1 B1 C3 115.01(13) . . ?
N1 B1 C9 121.61(13) . . ?
C3 B1 C9 123.36(13) . . ?
C1 N2 N1 116.48(12) . . ?
C7 C2 C3 120.88(13) . . ?
C7 C2 C1 120.70(13) . . ?
C3 C2 C1 118.39(13) . . ?
C10 C8 C14 120.59(13) . . ?
C10 C8 N1 119.74(12) . . ?
C14 C8 N1 119.65(12) . . ?
C19 C9 C15 116.60(13) . . ?
C19 C9 B1 122.66(12) . . ?
C15 C9 B1 120.70(12) . . ?
C8 C10 C11 119.30(13) . . ?
C12 C11 C10 120.40(14) . . ?
C11 C12 C13 119.94(14) . . ?
C14 C13 C12 120.06(14) . . ?
C13 C14 C8 119.68(13) . . ?
C16 C15 C9 121.77(14) . . ?
C15 C16 C17 120.05(14) . . ?
C18 C17 C16 119.67(14) . . ?
C19 C18 C17 119.90(14) . . ?
C18 C19 C9 122.01(13) . . ?
C4 C3 C2 117.60(13) . . ?
C4 C3 B1 125.21(13) . . ?
C2 C3 B1 117.15(13) . . ?
C5 C4 C3 121.19(14) . . ?
C6 C7 C2 119.85(14) . . ?
C7 C6 C5 120.27(14) . . ?
C4 C5 C6 120.17(14) . . ?

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
N2 N1 B1 C3 0.2(2) . . . . ?
C8 N1 B1 C3 177.52(12) . . . . ?
N2 N1 B1 C9 -178.26(12) . . . . ?
C8 N1 B1 C9 -1.0(2) . . . . ?
C2 C1 N2 N1 1.6(2) . . . . ?
B1 N1 N2 C1 -1.71(19) . . . . ?
C8 N1 N2 C1 -179.30(12) . . . . ?
N2 C1 C2 C7 178.26(14) . . . . ?
N2 C1 C2 C3 0.0(2) . . . . ?
N2 N1 C8 C10 -113.77(14) . . . . ?
B1 N1 C8 C10 68.59(18) . . . . ?
N2 N1 C8 C14 67.79(16) . . . . ?
B1 N1 C8 C14 -109.85(16) . . . . ?
N1 B1 C9 C19 49.7(2) . . . . ?
C3 B1 C9 C19 -128.69(15) . . . . ?
N1 B1 C9 C15 -132.92(15) . . . . ?
C3 B1 C9 C15 48.7(2) . . . . ?
C14 C8 C10 C11 1.3(2) . . . . ?
N1 C8 C10 C11 -177.16(12) . . . . ?
C8 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C8 0.5(2) . . . . ?
C10 C8 C14 C13 -1.4(2) . . . . ?
N1 C8 C14 C13 176.99(13) . . . . ?
C19 C9 C15 C16 -0.2(2) . . . . ?
B1 C9 C15 C16 -177.74(13) . . . . ?
C9 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C9 0.5(2) . . . . ?
C15 C9 C19 C18 -0.3(2) . . . . ?
B1 C9 C19 C18 177.24(13) . . . . ?
C7 C2 C3 C4 -2.0(2) . . . . ?
C1 C2 C3 C4 176.29(13) . . . . ?
C7 C2 C3 B1 -179.78(13) . . . . ?
C1 C2 C3 B1 -1.52(19) . . . . ?
N1 B1 C3 C4 -176.25(13) . . . . ?
C9 B1 C3 C4 2.2(2) . . . . ?
N1 B1 C3 C2 1.37(18) . . . . ?
C9 B1 C3 C2 179.84(13) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
B1 C3 C4 C5 179.44(13) . . . . ?
C3 C2 C7 C6 0.7(2) . . . . ?
C1 C2 C7 C6 -177.57(13) . . . . ?
C2 C7 C6 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C7 C6 C5 C4 -1.0(2) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-F
_database_code_depnum_ccdc_archive 'CCDC 2394207'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.4y (K.Radacki, 2005-23)'
_audit_creation_date             2024-05-08
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C19 H15 B F N2, C16 H36 N'
_chemical_formula_sum            'C35 H51 B F N3'
_chemical_formula_weight         543.59
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'


_cell_length_a                   9.81050(10)
_cell_length_b                   16.1727(2)
_cell_length_c                   20.3437(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.1460(10)
_cell_angle_gamma                90
_cell_volume                     3202.71(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26924
_cell_measurement_theta_min      3.4830
_cell_measurement_theta_max      72.6810

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0743
0 -1 0 0.1000
-1 -2 1 0.1226
-1 0 1 0.1183
-1 2 1 0.1083
0 1 0 0.1037
0 1 13 0.0058
0 -1 -13 0.0205
-5 -1 -6 0.0984
-1 -1 -13 0.0349

_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.979
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     17.00  65.00   0.50    0.79    --   58.44 -93.00 159.00   96
  2  ω    -66.00 -18.00   0.50    0.79    --  -60.13  93.00 -88.00   96
  3  ω    -75.00 -27.00   0.50    0.79    --  -69.55  93.00 -88.00   96
  4  ω     29.00  77.00   0.50    0.79    --   71.24 -93.00 159.00   96
  5  ω    -82.00 -34.00   0.50    0.79    --  -76.36  93.00 -88.00   96
  6  ω     40.00  88.00   0.50    0.79    --   82.26 -93.00 159.00   96
  7  ω     48.00  83.00   0.50    0.79    --   34.00  51.00 156.18   70
  8  ω    -91.00 -55.00   0.50    0.79    --  -42.00 -46.00 -35.75   72
  9  ω    -94.00 -59.00   0.50    0.79    --  -46.00 -51.00-148.83   70
 10  ω   -107.00 -72.00   0.50    0.79    --  -58.00 -49.00  46.58   70
 11  ω     16.00  66.00   0.50    0.79    --   58.44 -95.00 -30.00  100
 12  ω   -110.00 -75.00   0.50    0.79    --  -62.00 -51.00  94.19   70
 13  ω   -114.00 -79.00   0.50    0.79    --  -66.00 -51.00-167.75   70
 14  ω   -120.00 -83.00   0.50    0.79    --  -70.00 -46.00 130.80   74
 15  ω   -117.00 -85.00   0.50    0.79    --  -70.00 -58.00 -94.57   64
 16  ω   -121.00 -86.00   0.50    0.79    --  -74.00 -58.00 165.65   70
 17  ω   -124.00 -86.00   0.50    0.79    --  -74.00 -42.00-162.07   76
 18  ω   -122.00 -87.00   0.50    0.79    --  -74.00 -51.00  24.73   70
 19  ω    -92.00 -31.00   0.50    0.79    --  -76.36 112.00  60.00  122
 20  ω   -130.00 -72.00   0.50    0.79    --  -78.00 -22.00 -38.72  116
 21  ω    -97.00 -32.00   0.50    0.79    --  -78.00 114.00 -25.17  130
 22  ω   -130.00 -92.00   0.50    0.79    --  -79.50 -42.00 -53.81   76
 23  ω   -128.00 -93.00   0.50    0.79    --  -79.50 -50.00 105.03   70
 24  ω   -125.00 -91.00   0.50    0.79    --  -79.50 -60.00 -16.10   68
 25  ω   -126.00 -92.00   0.50    0.79    --  -79.50-123.00 117.04   68
 26  ω   -126.00 -91.00   0.50    0.79    --  -79.50 -59.00  69.20   70
 27  ω   -130.00 -91.00   0.50    0.79    --  -79.50 -39.00 141.33   78
 28  ω   -126.00 -93.00   0.50    0.79    --  -79.50-120.00 -41.76   66
 29  ω   -126.00 -92.00   0.50    0.79    --  -79.50-122.00-118.58   68
 30  ω   -130.00 -91.00   0.50    0.79    --  -79.50 -41.00 160.11   78
 31  ω   -124.00 -92.00   0.50    0.79    --  -79.50 -63.00-112.44   64
 32  ω   -125.00 -91.00   0.50    0.79    --  -79.50 -60.00-142.11   68
 33  ω   -107.00 -33.00   0.50    0.79    --  -79.50 137.00 142.84  148
 34  ω   -129.00 -93.00   0.50    0.79    --  -79.50 -47.00  90.07   72
 35  ω   -126.00 -92.00   0.50    0.79    --  -79.50-123.00 173.29   68
 36  ω   -127.00 -90.00   0.50    0.79    --  -79.50-127.00 -87.81   74
 37  ω    -97.00 -33.00   0.50    0.79    --  -79.50 115.00  80.64  128
 38  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00 -90.00  100
 39  ω     46.00 133.00   0.50    0.79    --   82.26  15.00   0.00  174
 40  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00 -60.00  100
 41  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00   0.00  100
 42  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00-120.00  100
 43  ω     37.00  93.00   0.50    0.79    --   82.26-112.00  90.00  112
 44  ω     37.00  93.00   0.50    0.79    --   82.26-112.00-120.00  112
 45  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00  60.00  100
 46  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00 150.00  100
 47  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00  90.00  100
 48  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00 -30.00  100
 49  ω     40.00  90.00   0.50    0.79    --   82.26 -95.00-180.00  100
 50  ω     42.00  93.00   0.50    0.79    --   85.25 -98.00  61.74  102
 51  ω     42.00  92.00   0.50    0.79    --   85.25 -99.00  27.25  100
 52  ω     42.00  93.00   0.50    0.79    --   85.25 -98.00 -38.12  102
 53  ω     25.00  54.00   0.50    0.79    --   14.00  61.00 -95.02   58
 54  ω     25.00  54.00   0.50    0.79    --   14.00  61.00  38.57   58
 55  ω     34.00  60.00   0.50    0.79    --   22.00  59.00  71.02   52
 56  ω     34.00  60.00   0.50    0.79    --   22.00  59.00 158.76   52
 57  ω     34.00  60.00   0.50    0.79    --   22.00  57.00 125.31   52
 58  ω     34.00  60.00   0.50    0.79    --   22.00  57.00-153.86   52
 59  ω    -87.00 -52.00   0.50    0.79    --  -38.00 -48.00-115.49   70
 60  ω    -86.00 -51.00   0.50    0.79    --  -38.00 -52.00 -70.26   70
 61  ω   -120.00 -88.00   0.50    0.79    --  -74.00 -59.00   0.16   64
 62  ω   -120.00 -86.00   0.50    0.79    --  -74.00 -60.00  45.68   68
 63  ω   -121.00 -86.00   0.50    0.79    --  -74.00 -55.00  81.95   70
 64  ω   -123.00 -87.00   0.50    0.79    --  -74.00 -46.00 -84.31   72
 65  ω   -121.00 -86.00   0.50    0.79    --  -74.00 -55.00 126.14   70
 66  ω   -122.00 -87.00   0.50    0.79    --  -74.00 -54.00-173.60   70
 67  ω   -126.00 -93.00   0.50    0.79    --  -79.50-120.00 -68.36   66
 68  ω   -127.00 -90.00   0.50    0.79    --  -79.50-126.00  60.60   74
 69  ω   -126.00 -92.00   0.50    0.79    --  -79.50-122.00  86.02   68
 70  ω   -126.00 -92.00   0.50    0.79    --  -79.50-123.00-162.36   68
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0669020000
_diffrn_orient_matrix_UB_12      -0.0543361000
_diffrn_orient_matrix_UB_13      0.0573630000
_diffrn_orient_matrix_UB_21      0.0408188000
_diffrn_orient_matrix_UB_22      0.0781699000
_diffrn_orient_matrix_UB_23      0.0410130000
_diffrn_orient_matrix_UB_31      -0.1374553000
_diffrn_orient_matrix_UB_32      -0.0032762000
_diffrn_orient_matrix_UB_33      0.0292195000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            72923
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.502
_diffrn_reflns_theta_max         75.085
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6364
_reflns_number_gt                5317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       
;
 CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))
;
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          
;
 The reflection [1 0 9] was removed from refinement as outliers. There is a 
 whole molecule disorder of the diazaborinin unit and the phenyl substituent 
 at N1 with an occupancy factor of 84% according to the second free variabel 
 of 0.84077. The atomic displacement parameters of the diazaborinin atoms 
 F1_1 to C7_21 and the phenyl atoms C1_2 to C6_21 were restraint with RIGU 
 keyword withesd = 0.016 in ShelXL input ('enhanced rigid bond' restraint for 
 all bonds in the connectivity list). The parameters of the diazaborinin 
 atoms F1_1 to C7_21 and the phenyl atoms C1_2 to C6_21 were restrained to 
 the same value with similarity restraint SIMU (esd = 0.032). The Uii 
 displacement parameters of the diazaborinin atoms F1_1 to C7_21 and the 
 phenyl atoms C1_2 to C6_21 were restrained with ISOR keyword with esd 0 
 0.008 to approximate isotropic behavior. The 1--2 and 1--3 distances of the 
 phenyl atoms C1_2 to C6_21 were restrained to the same values with SAME.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0455P)²+1.3475P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6364
_refine_ls_number_parameters     519
_refine_ls_number_restraints     780
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.043
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
F1_1 F 0.1275(5) 0.7746(3) 0.3458(3) 0.0290(7) Uani 0.841(3) 1 d . U P A 1
B1_1 B 0.0796(2) 0.69060(13) 0.32740(12) 0.0285(5) Uani 0.841(3) 1 d . U P A 1
N1_1 N -0.07952(15) 0.69134(10) 0.31218(8) 0.0292(4) Uani 0.841(3) 1 d . U P A
1
N2_1 N -0.15327(16) 0.69310(11) 0.25036(8) 0.0319(4) Uani 0.841(3) 1 d . U P A
1
C1_1 C -0.08929(19) 0.68401(12) 0.19896(9) 0.0325(5) Uani 0.841(3) 1 d . U P A
1
H1_1 H -0.143082 0.688223 0.156915 0.039 Uiso 0.841(3) 1 calc R U P A 1
C2_1 C 0.0557(3) 0.66808(13) 0.19892(16) 0.0301(5) Uani 0.841(3) 1 d . U P A 1
C3_1 C 0.1094(4) 0.6524(3) 0.13933(16) 0.0358(8) Uani 0.841(3) 1 d . U P A 1
H3_1 H 0.050293 0.654709 0.098656 0.043 Uiso 0.841(3) 1 calc R U P A 1
C4_1 C 0.2476(6) 0.6336(8) 0.1388(3) 0.0363(12) Uani 0.841(3) 1 d . U P A 1
H4_1 H 0.283486 0.623120 0.098386 0.044 Uiso 0.841(3) 1 calc R U P A 1
C5_1 C 0.3318(3) 0.6306(3) 0.19887(17) 0.0319(7) Uani 0.841(3) 1 d . U P A 1
H5_1 H 0.426337 0.617291 0.199663 0.038 Uiso 0.841(3) 1 calc R U P A 1
C6_1 C 0.2791(3) 0.64692(12) 0.25774(11) 0.0298(5) Uani 0.841(3) 1 d . U P A 1
H6_1 H 0.339097 0.644638 0.298135 0.036 Uiso 0.841(3) 1 calc R U P A 1
C7_1 C 0.1401(3) 0.66670(13) 0.25972(12) 0.0281(5) Uani 0.841(3) 1 d . U P A 1
F1_11 F 0.105(3) 0.7631(17) 0.3519(17) 0.035(4) Uani 0.159(3) 1 d . U P A 2
B1_11 B 0.0237(14) 0.6910(7) 0.3538(8) 0.034(3) Uani 0.159(3) 1 d . U P A 2
N1_11 N -0.0232(9) 0.6628(5) 0.2810(4) 0.032(2) Uani 0.159(3) 1 d . U P A 2
N2_11 N -0.1536(8) 0.6367(6) 0.2584(4) 0.031(2) Uani 0.159(3) 1 d . U P A 2
C1_11 C -0.2484(9) 0.6399(6) 0.2964(5) 0.030(2) Uani 0.159(3) 1 d . U P A 2
H1_11 H -0.334383 0.615750 0.280203 0.035 Uiso 0.159(3) 1 calc R U P A 2
C2_11 C -0.237(2) 0.6771(7) 0.3618(6) 0.023(2) Uani 0.159(3) 1 d . U P A 2
C3_11 C -0.350(2) 0.6782(15) 0.3930(12) 0.035(4) Uani 0.159(3) 1 d . U P A 2
H3A_11 H -0.435647 0.663065 0.368833 0.042 Uiso 0.159(3) 1 calc R U P A 2
C4_11 C -0.346(4) 0.704(2) 0.4700(19) 0.025(4) Uani 0.159(3) 1 d . U P A 2
H4A_11 H -0.410608 0.691228 0.499522 0.030 Uiso 0.159(3) 1 calc R U P A 2
C5_11 C -0.214(3) 0.7546(15) 0.4840(12) 0.034(4) Uani 0.159(3) 1 d . U P A 2
H5A_11 H -0.208108 0.792848 0.519725 0.041 Uiso 0.159(3) 1 calc R U P A 2
C6_11 C -0.1060(16) 0.7491(10) 0.4498(8) 0.035(3) Uani 0.159(3) 1 d . U P A 2
H6_11 H -0.021420 0.773410 0.467919 0.042 Uiso 0.159(3) 1 calc R U P A 2
C7_11 C -0.1129(15) 0.7092(8) 0.3889(9) 0.028(2) Uani 0.159(3) 1 d . U P A 2
C1_2 C -0.1669(4) 0.69587(15) 0.36235(13) 0.0299(5) Uani 0.841(3) 1 d D U P A 1
C2_2 C -0.1208(3) 0.73290(18) 0.42296(17) 0.0347(6) Uani 0.841(3) 1 d D U P A 1
H2_2 H -0.030833 0.755511 0.430493 0.042 Uiso 0.841(3) 1 calc R U P A 1
C3_2 C -0.2067(6) 0.7367(3) 0.4724(2) 0.0416(10) Uani 0.841(3) 1 d D U P A 1
H3_2 H -0.174656 0.760144 0.514344 0.050 Uiso 0.841(3) 1 calc R U P A 1
C4_2 C -0.3367(9) 0.7067(5) 0.4604(4) 0.0451(18) Uani 0.841(3) 1 d D U P A 1
H4_2 H -0.397294 0.713802 0.492879 0.054 Uiso 0.841(3) 1 calc R U P A 1
C5_2 C -0.3824(3) 0.6668(3) 0.40337(19) 0.0386(8) Uani 0.841(3) 1 d D U P A 1
H5_2 H -0.471086 0.642294 0.397684 0.046 Uiso 0.841(3) 1 calc R U P A 1
C6_2 C -0.2986(3) 0.66216(16) 0.35325(13) 0.0339(6) Uani 0.841(3) 1 d D U P A 1
H6_2 H -0.331266 0.635853 0.312569 0.041 Uiso 0.841(3) 1 calc R U P A 1
C1_21 C 0.0683(13) 0.6596(7) 0.2320(7) 0.024(2) Uani 0.159(3) 1 d D U P A 2
C2_21 C 0.0143(12) 0.6584(7) 0.1651(7) 0.033(2) Uani 0.159(3) 1 d D U P A 2
H2_21 H -0.081855 0.663930 0.152520 0.039 Uiso 0.159(3) 1 calc R U P A 2
C3_21 C 0.0996(18) 0.6494(17) 0.1186(8) 0.032(4) Uani 0.159(3) 1 d D U P A 2
H3_21 H 0.063880 0.649871 0.072989 0.039 Uiso 0.159(3) 1 calc R U P A 2
C4_21 C 0.236(3) 0.640(4) 0.1366(12) 0.031(6) Uani 0.159(3) 1 d D U P A 2
H4_21 H 0.293869 0.631511 0.103197 0.038 Uiso 0.159(3) 1 calc R U P A 2
C5_21 C 0.2929(16) 0.6414(14) 0.2029(10) 0.031(4) Uani 0.159(3) 1 d D U P A 2
H5_21 H 0.389045 0.634471 0.214650 0.038 Uiso 0.159(3) 1 calc R U P A 2
C6_21 C 0.2047(15) 0.6536(7) 0.2526(5) 0.019(2) Uani 0.159(3) 1 d D U P A 2
H6_21 H 0.239854 0.657453 0.298161 0.023 Uiso 0.159(3) 1 calc R U P A 2
C1_3 C 0.13123(15) 0.62717(9) 0.38879(8) 0.0308(3) Uani 1 1 d . . . . .
C2_3 C 0.26015(15) 0.64041(10) 0.42512(8) 0.0317(3) Uani 1 1 d . . . . .
H2_3 H 0.308414 0.689885 0.417999 0.038 Uiso 1 1 calc R U . . .
C3_3 C 0.31999(17) 0.58358(11) 0.47131(8) 0.0372(4) Uani 1 1 d . . . . .
H3_3 H 0.408191 0.594290 0.494686 0.045 Uiso 1 1 calc R U . . .
C4_3 C 0.25133(19) 0.51153(11) 0.48325(8) 0.0417(4) Uani 1 1 d . . . . .
H4_3 H 0.291801 0.472546 0.514751 0.050 Uiso 1 1 calc R U . . .
C5_3 C 0.12274(18) 0.49686(10) 0.44872(8) 0.0382(4) Uani 1 1 d . . . . .
H5_3 H 0.074369 0.447725 0.456721 0.046 Uiso 1 1 calc R U . . .
C6_3 C 0.06454(16) 0.55376(10) 0.40250(8) 0.0328(3) Uani 1 1 d . . . . .
H6_3 H -0.023673 0.542540 0.379335 0.039 Uiso 1 1 calc R U . . .
N3_4 N 0.47267(12) 0.89250(7) 0.27819(6) 0.0269(3) Uani 1 1 d . . . . .
C1_5 C 0.43181(15) 0.85779(9) 0.34240(7) 0.0283(3) Uani 1 1 d . . . . .
H1A_5 H 0.360174 0.815198 0.331271 0.034 Uiso 1 1 calc R U . . .
H1B_5 H 0.512763 0.829930 0.366684 0.034 Uiso 1 1 calc R U . . .
C2_5 C 0.37815(16) 0.92060(10) 0.38830(8) 0.0325(3) Uani 1 1 d . . . . .
H2A_5 H 0.443283 0.967470 0.395179 0.039 Uiso 1 1 calc R U . . .
H2B_5 H 0.288770 0.942419 0.367509 0.039 Uiso 1 1 calc R U . . .
C3_5 C 0.36030(19) 0.88216(11) 0.45465(8) 0.0389(4) Uani 1 1 d . . . . .
H3A_5 H 0.449793 0.860118 0.475094 0.047 Uiso 1 1 calc R U . . .
H3B_5 H 0.295385 0.835210 0.447489 0.047 Uiso 1 1 calc R U . . .
C4_5 C 0.30673(18) 0.94357(11) 0.50198(9) 0.0408(4) Uani 1 1 d . . . . .
H4A_5 H 0.299588 0.916375 0.544462 0.061 Uiso 1 1 calc R U . . .
H4B_5 H 0.215915 0.963436 0.483002 0.061 Uiso 1 1 calc R U . . .
H4C_5 H 0.370178 0.990446 0.508949 0.061 Uiso 1 1 calc R U . . .
C1_6 C 0.58975(15) 0.95414(9) 0.29143(8) 0.0299(3) Uani 1 1 d . . . . .
H1A_6 H 0.614100 0.973938 0.248340 0.036 Uiso 1 1 calc R U . . .
H1B_6 H 0.556531 1.002410 0.314787 0.036 Uiso 1 1 calc R U . . .
C2_6 C 0.71909(15) 0.92154(10) 0.33197(9) 0.0343(4) Uani 1 1 d . . . . .
H2A_6 H 0.747255 0.869028 0.312589 0.041 Uiso 1 1 calc R U . . .
H2B_6 H 0.700645 0.910380 0.377887 0.041 Uiso 1 1 calc R U . . .
C3_6 C 0.83452(16) 0.98511(10) 0.33258(9) 0.0372(4) Uani 1 1 d . . . . .
H3A_6 H 0.858131 0.992228 0.287003 0.045 Uiso 1 1 calc R U . . .
H3B_6 H 0.802165 1.039085 0.347601 0.045 Uiso 1 1 calc R U . . .
C4_6 C 0.96260(17) 0.95881(12) 0.37811(10) 0.0471(5) Uani 1 1 d . . . . .
H4A_6 H 1.033161 1.001732 0.378346 0.071 Uiso 1 1 calc R U . . .
H4B_6 H 0.997592 0.906778 0.362055 0.071 Uiso 1 1 calc R U . . .
H4C_6 H 0.939298 0.951008 0.423163 0.071 Uiso 1 1 calc R U . . .
C1_7 C 0.51503(15) 0.81941(9) 0.23839(7) 0.0288(3) Uani 1 1 d . . . . .
H1A_7 H 0.584674 0.786979 0.266916 0.035 Uiso 1 1 calc R U . . .
H1B_7 H 0.433858 0.783389 0.227240 0.035 Uiso 1 1 calc R U . . .
C2_7 C 0.57305(16) 0.84055(10) 0.17490(8) 0.0332(3) Uani 1 1 d . . . . .
H2A_7 H 0.666381 0.864020 0.185542 0.040 Uiso 1 1 calc R U . . .
H2B_7 H 0.514350 0.882676 0.149987 0.040 Uiso 1 1 calc R U . . .
C3_7 C 0.57947(17) 0.76340(10) 0.13241(8) 0.0355(4) Uani 1 1 d . . . . .
H3A_7 H 0.629840 0.719483 0.159277 0.043 Uiso 1 1 calc R U . . .
H3B_7 H 0.484963 0.743263 0.118571 0.043 Uiso 1 1 calc R U . . .
C4_7 C 0.64994(19) 0.77930(11) 0.07110(9) 0.0421(4) Uani 1 1 d . . . . .
H4A_7 H 0.652685 0.727939 0.045745 0.063 Uiso 1 1 calc R U . . .
H4B_7 H 0.743841 0.798831 0.084524 0.063 Uiso 1 1 calc R U . . .
H4C_7 H 0.598673 0.821390 0.043541 0.063 Uiso 1 1 calc R U . . .
C1_8 C 0.35336(14) 0.93931(9) 0.24008(8) 0.0288(3) Uani 1 1 d . . . . .
H1A_8 H 0.325490 0.984070 0.268805 0.035 Uiso 1 1 calc R U . . .
H1B_8 H 0.386476 0.965726 0.201124 0.035 Uiso 1 1 calc R U . . .
C2_8 C 0.22705(15) 0.88804(10) 0.21611(8) 0.0328(3) Uani 1 1 d . . . . .
H2A_8 H 0.197298 0.856696 0.253626 0.039 Uiso 1 1 calc R U . . .
H2B_8 H 0.249313 0.847963 0.182237 0.039 Uiso 1 1 calc R U . . .
C3_8 C 0.11145(16) 0.94523(10) 0.18646(9) 0.0362(4) Uani 1 1 d . . . . .
H3A_8 H 0.088280 0.984078 0.221011 0.043 Uiso 1 1 calc R U . . .
H3B_8 H 0.143685 0.978190 0.150400 0.043 Uiso 1 1 calc R U . . .
C4_8 C -0.01685(18) 0.89752(12) 0.15915(10) 0.0483(5) Uani 1 1 d . . . . .
H4A_8 H -0.087753 0.936350 0.140181 0.073 Uiso 1 1 calc R U . . .
H4B_8 H -0.050882 0.866212 0.195004 0.073 Uiso 1 1 calc R U . . .
H4C_8 H 0.005446 0.859270 0.124686 0.073 Uiso 1 1 calc R U . . .


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
F1_1 B1_1 1.470(5) . ?
B1_1 N1_1 1.553(3) . ?
B1_1 C7_1 1.613(4) . ?
B1_1 C1_3 1.647(3) . ?
N1_1 N2_1 1.371(2) . ?
N1_1 C1_2 1.414(3) . ?
N2_1 C1_1 1.293(2) . ?
C1_1 C2_1 1.446(3) . ?
C1_1 H1_1 0.9500 . ?
C2_1 C7_1 1.400(3) . ?
C2_1 C3_1 1.403(4) . ?
C3_1 C4_1 1.391(5) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.388(5) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.387(4) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.407(3) . ?
C6_1 H6_1 0.9500 . ?
F1_11 B1_11 1.42(2) . ?
B1_11 N1_11 1.563(17) . ?
B1_11 C1_3 1.581(12) . ?
B1_11 C7_11 1.62(2) . ?
N1_11 N2_11 1.372(11) . ?
N1_11 C1_21 1.423(15) . ?
N2_11 C1_11 1.282(13) . ?
C1_11 C2_11 1.452(16) . ?
C1_11 H1_11 0.9500 . ?
C2_11 C3_11 1.35(3) . ?
C2_11 C7_11 1.371(18) . ?
C3_11 C4_11 1.62(5) . ?
C3_11 H3A_11 0.9500 . ?
C4_11 C5_11 1.53(5) . ?
C4_11 H4A_11 0.9500 . ?
C5_11 C6_11 1.34(3) . ?
C5_11 H5A_11 0.9500 . ?
C6_11 C7_11 1.392(18) . ?
C6_11 H6_11 0.9500 . ?
C1_2 C6_2 1.394(3) . ?
C1_2 C2_2 1.395(4) . ?
C2_2 C3_2 1.392(6) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.358(10) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.353(9) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.389(4) . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
C1_21 C6_21 1.355(13) . ?
C1_21 C2_21 1.398(13) . ?
C2_21 C3_21 1.347(16) . ?
C2_21 H2_21 0.9500 . ?
C3_21 C4_21 1.35(2) . ?
C3_21 H3_21 0.9500 . ?
C4_21 C5_21 1.397(19) . ?
C4_21 H4_21 0.9500 . ?
C5_21 C6_21 1.425(15) . ?
C5_21 H5_21 0.9500 . ?
C6_21 H6_21 0.9500 . ?
C1_3 C2_3 1.400(2) . ?
C1_3 C6_3 1.400(2) . ?
C2_3 C3_3 1.391(2) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.382(2) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.386(2) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.387(2) . ?
C5_3 H5_3 0.9500 . ?
C6_3 H6_3 0.9500 . ?
N3_4 C1_6 1.5194(18) . ?
N3_4 C1_7 1.5196(18) . ?
N3_4 C1_5 1.5207(19) . ?
N3_4 C1_8 1.5226(17) . ?
C1_5 C2_5 1.518(2) . ?
C1_5 H1A_5 0.9900 . ?
C1_5 H1B_5 0.9900 . ?
C2_5 C3_5 1.516(2) . ?
C2_5 H2A_5 0.9900 . ?
C2_5 H2B_5 0.9900 . ?
C3_5 C4_5 1.522(2) . ?
C3_5 H3A_5 0.9900 . ?
C3_5 H3B_5 0.9900 . ?
C4_5 H4A_5 0.9800 . ?
C4_5 H4B_5 0.9800 . ?
C4_5 H4C_5 0.9800 . ?
C1_6 C2_6 1.519(2) . ?
C1_6 H1A_6 0.9900 . ?
C1_6 H1B_6 0.9900 . ?
C2_6 C3_6 1.528(2) . ?
C2_6 H2A_6 0.9900 . ?
C2_6 H2B_6 0.9900 . ?
C3_6 C4_6 1.526(2) . ?
C3_6 H3A_6 0.9900 . ?
C3_6 H3B_6 0.9900 . ?
C4_6 H4A_6 0.9800 . ?
C4_6 H4B_6 0.9800 . ?
C4_6 H4C_6 0.9800 . ?
C1_7 C2_7 1.514(2) . ?
C1_7 H1A_7 0.9900 . ?
C1_7 H1B_7 0.9900 . ?
C2_7 C3_7 1.524(2) . ?
C2_7 H2A_7 0.9900 . ?
C2_7 H2B_7 0.9900 . ?
C3_7 C4_7 1.521(2) . ?
C3_7 H3A_7 0.9900 . ?
C3_7 H3B_7 0.9900 . ?
C4_7 H4A_7 0.9800 . ?
C4_7 H4B_7 0.9800 . ?
C4_7 H4C_7 0.9800 . ?
C1_8 C2_8 1.520(2) . ?
C1_8 H1A_8 0.9900 . ?
C1_8 H1B_8 0.9900 . ?
C2_8 C3_8 1.528(2) . ?
C2_8 H2A_8 0.9900 . ?
C2_8 H2B_8 0.9900 . ?
C3_8 C4_8 1.521(2) . ?
C3_8 H3A_8 0.9900 . ?
C3_8 H3B_8 0.9900 . ?
C4_8 H4A_8 0.9800 . ?
C4_8 H4B_8 0.9800 . ?
C4_8 H4C_8 0.9800 . ?

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
F1_1 B1_1 N1_1 109.0(2) . . ?
F1_1 B1_1 C7_1 107.4(3) . . ?
N1_1 B1_1 C7_1 107.41(18) . . ?
F1_1 B1_1 C1_3 108.9(3) . . ?
N1_1 B1_1 C1_3 111.28(17) . . ?
C7_1 B1_1 C1_3 112.76(17) . . ?
N2_1 N1_1 C1_2 111.28(19) . . ?
N2_1 N1_1 B1_1 125.86(17) . . ?
C1_2 N1_1 B1_1 122.7(2) . . ?
C1_1 N2_1 N1_1 119.04(16) . . ?
N2_1 C1_1 C2_1 126.7(2) . . ?
N2_1 C1_1 H1_1 116.7 . . ?
C2_1 C1_1 H1_1 116.7 . . ?
C7_1 C2_1 C3_1 121.1(2) . . ?
C7_1 C2_1 C1_1 118.4(3) . . ?
C3_1 C2_1 C1_1 120.5(3) . . ?
C4_1 C3_1 C2_1 121.1(3) . . ?
C4_1 C3_1 H3_1 119.5 . . ?
C2_1 C3_1 H3_1 119.5 . . ?
C5_1 C4_1 C3_1 118.4(4) . . ?
C5_1 C4_1 H4_1 120.8 . . ?
C3_1 C4_1 H4_1 120.8 . . ?
C6_1 C5_1 C4_1 120.5(3) . . ?
C6_1 C5_1 H5_1 119.7 . . ?
C4_1 C5_1 H5_1 119.7 . . ?
C5_1 C6_1 C7_1 122.3(2) . . ?
C5_1 C6_1 H6_1 118.8 . . ?
C7_1 C6_1 H6_1 118.8 . . ?
C2_1 C7_1 C6_1 116.5(2) . . ?
C2_1 C7_1 B1_1 120.7(2) . . ?
C6_1 C7_1 B1_1 122.7(2) . . ?
F1_11 B1_11 N1_11 108.4(18) . . ?
F1_11 B1_11 C1_3 101.7(16) . . ?
N1_11 B1_11 C1_3 109.7(9) . . ?
F1_11 B1_11 C7_11 111.3(16) . . ?
N1_11 B1_11 C7_11 108.0(11) . . ?
C1_3 B1_11 C7_11 117.4(11) . . ?
N2_11 N1_11 C1_21 113.4(9) . . ?
N2_11 N1_11 B1_11 124.0(10) . . ?
C1_21 N1_11 B1_11 122.5(10) . . ?
C1_11 N2_11 N1_11 120.2(8) . . ?
N2_11 C1_11 C2_11 126.0(11) . . ?
N2_11 C1_11 H1_11 117.0 . . ?
C2_11 C1_11 H1_11 117.0 . . ?
C3_11 C2_11 C7_11 123.2(14) . . ?
C3_11 C2_11 C1_11 117.4(18) . . ?
C7_11 C2_11 C1_11 119.4(15) . . ?
C2_11 C3_11 C4_11 122(2) . . ?
C2_11 C3_11 H3A_11 118.8 . . ?
C4_11 C3_11 H3A_11 118.8 . . ?
C5_11 C4_11 C3_11 104(3) . . ?
C5_11 C4_11 H4A_11 128.1 . . ?
C3_11 C4_11 H4A_11 128.1 . . ?
C6_11 C5_11 C4_11 125(2) . . ?
C6_11 C5_11 H5A_11 117.5 . . ?
C4_11 C5_11 H5A_11 117.5 . . ?
C5_11 C6_11 C7_11 122.6(16) . . ?
C5_11 C6_11 H6_11 118.7 . . ?
C7_11 C6_11 H6_11 118.7 . . ?
C2_11 C7_11 C6_11 118.4(13) . . ?
C2_11 C7_11 B1_11 119.5(15) . . ?
C6_11 C7_11 B1_11 121.7(15) . . ?
C6_2 C1_2 C2_2 118.6(2) . . ?
C6_2 C1_2 N1_1 121.3(3) . . ?
C2_2 C1_2 N1_1 120.1(3) . . ?
C3_2 C2_2 C1_2 120.0(3) . . ?
C3_2 C2_2 H2_2 120.0 . . ?
C1_2 C2_2 H2_2 120.0 . . ?
C4_2 C3_2 C2_2 119.5(5) . . ?
C4_2 C3_2 H3_2 120.2 . . ?
C2_2 C3_2 H3_2 120.2 . . ?
C5_2 C4_2 C3_2 122.0(6) . . ?
C5_2 C4_2 H4_2 119.0 . . ?
C3_2 C4_2 H4_2 119.0 . . ?
C4_2 C5_2 C6_2 119.4(4) . . ?
C4_2 C5_2 H5_2 120.3 . . ?
C6_2 C5_2 H5_2 120.3 . . ?
C5_2 C6_2 C1_2 120.3(3) . . ?
C5_2 C6_2 H6_2 119.8 . . ?
C1_2 C6_2 H6_2 119.8 . . ?
C6_21 C1_21 C2_21 122.7(11) . . ?
C6_21 C1_21 N1_11 118.0(12) . . ?
C2_21 C1_21 N1_11 119.1(11) . . ?
C3_21 C2_21 C1_21 119.4(12) . . ?
C3_21 C2_21 H2_21 120.3 . . ?
C1_21 C2_21 H2_21 120.3 . . ?
C4_21 C3_21 C2_21 120.2(16) . . ?
C4_21 C3_21 H3_21 119.9 . . ?
C2_21 C3_21 H3_21 119.9 . . ?
C3_21 C4_21 C5_21 122(2) . . ?
C3_21 C4_21 H4_21 119.1 . . ?
C5_21 C4_21 H4_21 119.1 . . ?
C4_21 C5_21 C6_21 118.7(15) . . ?
C4_21 C5_21 H5_21 120.6 . . ?
C6_21 C5_21 H5_21 120.6 . . ?
C1_21 C6_21 C5_21 117.0(10) . . ?
C1_21 C6_21 H6_21 121.5 . . ?
C5_21 C6_21 H6_21 121.5 . . ?
C2_3 C1_3 C6_3 116.00(14) . . ?
C2_3 C1_3 B1_11 130.3(5) . . ?
C6_3 C1_3 B1_11 110.0(5) . . ?
C2_3 C1_3 B1_1 118.54(15) . . ?
C6_3 C1_3 B1_1 124.89(14) . . ?
C3_3 C2_3 C1_3 122.23(15) . . ?
C3_3 C2_3 H2_3 118.9 . . ?
C1_3 C2_3 H2_3 118.9 . . ?
C4_3 C3_3 C2_3 120.11(15) . . ?
C4_3 C3_3 H3_3 119.9 . . ?
C2_3 C3_3 H3_3 119.9 . . ?
C3_3 C4_3 C5_3 119.20(15) . . ?
C3_3 C4_3 H4_3 120.4 . . ?
C5_3 C4_3 H4_3 120.4 . . ?
C4_3 C5_3 C6_3 120.14(16) . . ?
C4_3 C5_3 H5_3 119.9 . . ?
C6_3 C5_3 H5_3 119.9 . . ?
C5_3 C6_3 C1_3 122.31(15) . . ?
C5_3 C6_3 H6_3 118.8 . . ?
C1_3 C6_3 H6_3 118.8 . . ?
C1_6 N3_4 C1_7 110.73(11) . . ?
C1_6 N3_4 C1_5 111.36(11) . . ?
C1_7 N3_4 C1_5 106.82(11) . . ?
C1_6 N3_4 C1_8 106.28(11) . . ?
C1_7 N3_4 C1_8 111.05(11) . . ?
C1_5 N3_4 C1_8 110.67(11) . . ?
C2_5 C1_5 N3_4 115.47(12) . . ?
C2_5 C1_5 H1A_5 108.4 . . ?
N3_4 C1_5 H1A_5 108.4 . . ?
C2_5 C1_5 H1B_5 108.4 . . ?
N3_4 C1_5 H1B_5 108.4 . . ?
H1A_5 C1_5 H1B_5 107.5 . . ?
C3_5 C2_5 C1_5 111.14(13) . . ?
C3_5 C2_5 H2A_5 109.4 . . ?
C1_5 C2_5 H2A_5 109.4 . . ?
C3_5 C2_5 H2B_5 109.4 . . ?
C1_5 C2_5 H2B_5 109.4 . . ?
H2A_5 C2_5 H2B_5 108.0 . . ?
C2_5 C3_5 C4_5 112.52(14) . . ?
C2_5 C3_5 H3A_5 109.1 . . ?
C4_5 C3_5 H3A_5 109.1 . . ?
C2_5 C3_5 H3B_5 109.1 . . ?
C4_5 C3_5 H3B_5 109.1 . . ?
H3A_5 C3_5 H3B_5 107.8 . . ?
C3_5 C4_5 H4A_5 109.5 . . ?
C3_5 C4_5 H4B_5 109.5 . . ?
H4A_5 C4_5 H4B_5 109.5 . . ?
C3_5 C4_5 H4C_5 109.5 . . ?
H4A_5 C4_5 H4C_5 109.5 . . ?
H4B_5 C4_5 H4C_5 109.5 . . ?
C2_6 C1_6 N3_4 115.50(12) . . ?
C2_6 C1_6 H1A_6 108.4 . . ?
N3_4 C1_6 H1A_6 108.4 . . ?
C2_6 C1_6 H1B_6 108.4 . . ?
N3_4 C1_6 H1B_6 108.4 . . ?
H1A_6 C1_6 H1B_6 107.5 . . ?
C1_6 C2_6 C3_6 109.81(13) . . ?
C1_6 C2_6 H2A_6 109.7 . . ?
C3_6 C2_6 H2A_6 109.7 . . ?
C1_6 C2_6 H2B_6 109.7 . . ?
C3_6 C2_6 H2B_6 109.7 . . ?
H2A_6 C2_6 H2B_6 108.2 . . ?
C4_6 C3_6 C2_6 111.76(14) . . ?
C4_6 C3_6 H3A_6 109.3 . . ?
C2_6 C3_6 H3A_6 109.3 . . ?
C4_6 C3_6 H3B_6 109.3 . . ?
C2_6 C3_6 H3B_6 109.3 . . ?
H3A_6 C3_6 H3B_6 107.9 . . ?
C3_6 C4_6 H4A_6 109.5 . . ?
C3_6 C4_6 H4B_6 109.5 . . ?
H4A_6 C4_6 H4B_6 109.5 . . ?
C3_6 C4_6 H4C_6 109.5 . . ?
H4A_6 C4_6 H4C_6 109.5 . . ?
H4B_6 C4_6 H4C_6 109.5 . . ?
C2_7 C1_7 N3_4 115.83(12) . . ?
C2_7 C1_7 H1A_7 108.3 . . ?
N3_4 C1_7 H1A_7 108.3 . . ?
C2_7 C1_7 H1B_7 108.3 . . ?
N3_4 C1_7 H1B_7 108.3 . . ?
H1A_7 C1_7 H1B_7 107.4 . . ?
C1_7 C2_7 C3_7 110.22(13) . . ?
C1_7 C2_7 H2A_7 109.6 . . ?
C3_7 C2_7 H2A_7 109.6 . . ?
C1_7 C2_7 H2B_7 109.6 . . ?
C3_7 C2_7 H2B_7 109.6 . . ?
H2A_7 C2_7 H2B_7 108.1 . . ?
C4_7 C3_7 C2_7 112.44(14) . . ?
C4_7 C3_7 H3A_7 109.1 . . ?
C2_7 C3_7 H3A_7 109.1 . . ?
C4_7 C3_7 H3B_7 109.1 . . ?
C2_7 C3_7 H3B_7 109.1 . . ?
H3A_7 C3_7 H3B_7 107.8 . . ?
C3_7 C4_7 H4A_7 109.5 . . ?
C3_7 C4_7 H4B_7 109.5 . . ?
H4A_7 C4_7 H4B_7 109.5 . . ?
C3_7 C4_7 H4C_7 109.5 . . ?
H4A_7 C4_7 H4C_7 109.5 . . ?
H4B_7 C4_7 H4C_7 109.5 . . ?
C2_8 C1_8 N3_4 115.88(12) . . ?
C2_8 C1_8 H1A_8 108.3 . . ?
N3_4 C1_8 H1A_8 108.3 . . ?
C2_8 C1_8 H1B_8 108.3 . . ?
N3_4 C1_8 H1B_8 108.3 . . ?
H1A_8 C1_8 H1B_8 107.4 . . ?
C1_8 C2_8 C3_8 109.38(12) . . ?
C1_8 C2_8 H2A_8 109.8 . . ?
C3_8 C2_8 H2A_8 109.8 . . ?
C1_8 C2_8 H2B_8 109.8 . . ?
C3_8 C2_8 H2B_8 109.8 . . ?
H2A_8 C2_8 H2B_8 108.2 . . ?
C4_8 C3_8 C2_8 112.14(14) . . ?
C4_8 C3_8 H3A_8 109.2 . . ?
C2_8 C3_8 H3A_8 109.2 . . ?
C4_8 C3_8 H3B_8 109.2 . . ?
C2_8 C3_8 H3B_8 109.2 . . ?
H3A_8 C3_8 H3B_8 107.9 . . ?
C3_8 C4_8 H4A_8 109.5 . . ?
C3_8 C4_8 H4B_8 109.5 . . ?
H4A_8 C4_8 H4B_8 109.5 . . ?
C3_8 C4_8 H4C_8 109.5 . . ?
H4A_8 C4_8 H4C_8 109.5 . . ?
H4B_8 C4_8 H4C_8 109.5 . . ?

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
F1_1 B1_1 N1_1 N2_1 100.4(3) . . . . ?
C7_1 B1_1 N1_1 N2_1 -15.6(2) . . . . ?
C1_3 B1_1 N1_1 N2_1 -139.42(18) . . . . ?
F1_1 B1_1 N1_1 C1_2 -75.1(3) . . . . ?
C7_1 B1_1 N1_1 C1_2 168.85(18) . . . . ?
C1_3 B1_1 N1_1 C1_2 45.0(2) . . . . ?
C1_2 N1_1 N2_1 C1_1 -175.51(19) . . . . ?
B1_1 N1_1 N2_1 C1_1 8.5(3) . . . . ?
N1_1 N2_1 C1_1 C2_1 2.9(3) . . . . ?
N2_1 C1_1 C2_1 C7_1 -4.0(3) . . . . ?
N2_1 C1_1 C2_1 C3_1 174.4(3) . . . . ?
C7_1 C2_1 C3_1 C4_1 1.1(8) . . . . ?
C1_1 C2_1 C3_1 C4_1 -177.3(7) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.0(13) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.7(13) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.2(8) . . . . ?
C3_1 C2_1 C7_1 C6_1 -1.5(4) . . . . ?
C1_1 C2_1 C7_1 C6_1 176.92(19) . . . . ?
C3_1 C2_1 C7_1 B1_1 176.0(3) . . . . ?
C1_1 C2_1 C7_1 B1_1 -5.6(3) . . . . ?
C5_1 C6_1 C7_1 C2_1 0.9(4) . . . . ?
C5_1 C6_1 C7_1 B1_1 -176.6(3) . . . . ?
F1_1 B1_1 C7_1 C2_1 -103.6(3) . . . . ?
N1_1 B1_1 C7_1 C2_1 13.5(3) . . . . ?
C1_3 B1_1 C7_1 C2_1 136.46(19) . . . . ?
F1_1 B1_1 C7_1 C6_1 73.8(3) . . . . ?
N1_1 B1_1 C7_1 C6_1 -169.16(19) . . . . ?
C1_3 B1_1 C7_1 C6_1 -46.2(3) . . . . ?
F1_11 B1_11 N1_11 N2_11 -137.0(17) . . . . ?
C1_3 B1_11 N1_11 N2_11 112.9(10) . . . . ?
C7_11 B1_11 N1_11 N2_11 -16.3(13) . . . . ?
F1_11 B1_11 N1_11 C1_21 45.0(19) . . . . ?
C1_3 B1_11 N1_11 C1_21 -65.2(12) . . . . ?
C7_11 B1_11 N1_11 C1_21 165.7(9) . . . . ?
C1_21 N1_11 N2_11 C1_11 -176.8(9) . . . . ?
B1_11 N1_11 N2_11 C1_11 5.0(15) . . . . ?
N1_11 N2_11 C1_11 C2_11 6.5(16) . . . . ?
N2_11 C1_11 C2_11 C3_11 176.7(14) . . . . ?
N2_11 C1_11 C2_11 C7_11 -3.2(16) . . . . ?
C7_11 C2_11 C3_11 C4_11 -10(3) . . . . ?
C1_11 C2_11 C3_11 C4_11 170(2) . . . . ?
C2_11 C3_11 C4_11 C5_11 21(3) . . . . ?
C3_11 C4_11 C5_11 C6_11 -23(4) . . . . ?
C4_11 C5_11 C6_11 C7_11 14(4) . . . . ?
C3_11 C2_11 C7_11 C6_11 -4(2) . . . . ?
C1_11 C2_11 C7_11 C6_11 176.0(12) . . . . ?
C3_11 C2_11 C7_11 B1_11 169.4(15) . . . . ?
C1_11 C2_11 C7_11 B1_11 -10.7(16) . . . . ?
C5_11 C6_11 C7_11 C2_11 3(2) . . . . ?
C5_11 C6_11 C7_11 B1_11 -170.6(17) . . . . ?
F1_11 B1_11 C7_11 C2_11 137.3(19) . . . . ?
N1_11 B1_11 C7_11 C2_11 18.5(14) . . . . ?
C1_3 B1_11 C7_11 C2_11 -106.1(12) . . . . ?
F1_11 B1_11 C7_11 C6_11 -50(2) . . . . ?
N1_11 B1_11 C7_11 C6_11 -168.5(12) . . . . ?
C1_3 B1_11 C7_11 C6_11 66.9(15) . . . . ?
N2_1 N1_1 C1_2 C6_2 31.8(3) . . . . ?
B1_1 N1_1 C1_2 C6_2 -152.1(2) . . . . ?
N2_1 N1_1 C1_2 C2_2 -149.7(2) . . . . ?
B1_1 N1_1 C1_2 C2_2 26.4(3) . . . . ?
C6_2 C1_2 C2_2 C3_2 -1.0(4) . . . . ?
N1_1 C1_2 C2_2 C3_2 -179.5(3) . . . . ?
C1_2 C2_2 C3_2 C4_2 -2.2(7) . . . . ?
C2_2 C3_2 C4_2 C5_2 5.5(10) . . . . ?
C3_2 C4_2 C5_2 C6_2 -5.4(10) . . . . ?
C4_2 C5_2 C6_2 C1_2 2.0(6) . . . . ?
C2_2 C1_2 C6_2 C5_2 1.1(4) . . . . ?
N1_1 C1_2 C6_2 C5_2 179.6(3) . . . . ?
N2_11 N1_11 C1_21 C6_21 -155.9(10) . . . . ?
B1_11 N1_11 C1_21 C6_21 22.3(14) . . . . ?
N2_11 N1_11 C1_21 C2_21 20.9(13) . . . . ?
B1_11 N1_11 C1_21 C2_21 -160.8(10) . . . . ?
C6_21 C1_21 C2_21 C3_21 1(2) . . . . ?
N1_11 C1_21 C2_21 C3_21 -175.3(15) . . . . ?
C1_21 C2_21 C3_21 C4_21 1(4) . . . . ?
C2_21 C3_21 C4_21 C5_21 -2(7) . . . . ?
C3_21 C4_21 C5_21 C6_21 0(7) . . . . ?
C2_21 C1_21 C6_21 C5_21 -3.4(19) . . . . ?
N1_11 C1_21 C6_21 C5_21 173.3(13) . . . . ?
C4_21 C5_21 C6_21 C1_21 3(4) . . . . ?
F1_11 B1_11 C1_3 C2_3 16.0(19) . . . . ?
N1_11 B1_11 C1_3 C2_3 130.5(6) . . . . ?
C7_11 B1_11 C1_3 C2_3 -105.7(10) . . . . ?
F1_11 B1_11 C1_3 C6_3 172.8(15) . . . . ?
N1_11 B1_11 C1_3 C6_3 -72.7(10) . . . . ?
C7_11 B1_11 C1_3 C6_3 51.1(11) . . . . ?
F1_1 B1_1 C1_3 C2_3 -36.3(3) . . . . ?
N1_1 B1_1 C1_3 C2_3 -156.45(15) . . . . ?
C7_1 B1_1 C1_3 C2_3 82.8(2) . . . . ?
F1_1 B1_1 C1_3 C6_3 152.7(2) . . . . ?
N1_1 B1_1 C1_3 C6_3 32.6(3) . . . . ?
C7_1 B1_1 C1_3 C6_3 -88.2(2) . . . . ?
C6_3 C1_3 C2_3 C3_3 1.1(2) . . . . ?
B1_11 C1_3 C2_3 C3_3 156.8(8) . . . . ?
B1_1 C1_3 C2_3 C3_3 -170.69(17) . . . . ?
C1_3 C2_3 C3_3 C4_3 -0.8(3) . . . . ?
C2_3 C3_3 C4_3 C5_3 0.0(3) . . . . ?
C3_3 C4_3 C5_3 C6_3 0.4(3) . . . . ?
C4_3 C5_3 C6_3 C1_3 0.0(3) . . . . ?
C2_3 C1_3 C6_3 C5_3 -0.7(2) . . . . ?
B1_11 C1_3 C6_3 C5_3 -161.1(6) . . . . ?
B1_1 C1_3 C6_3 C5_3 170.51(18) . . . . ?
C1_6 N3_4 C1_5 C2_5 62.18(15) . . . . ?
C1_7 N3_4 C1_5 C2_5 -176.81(12) . . . . ?
C1_8 N3_4 C1_5 C2_5 -55.80(15) . . . . ?
N3_4 C1_5 C2_5 C3_5 -171.69(12) . . . . ?
C1_5 C2_5 C3_5 C4_5 179.92(13) . . . . ?
C1_7 N3_4 C1_6 C2_6 -61.84(17) . . . . ?
C1_5 N3_4 C1_6 C2_6 56.85(17) . . . . ?
C1_8 N3_4 C1_6 C2_6 177.45(13) . . . . ?
N3_4 C1_6 C2_6 C3_6 171.51(13) . . . . ?
C1_6 C2_6 C3_6 C4_6 174.54(15) . . . . ?
C1_6 N3_4 C1_7 C2_7 -52.94(16) . . . . ?
C1_5 N3_4 C1_7 C2_7 -174.35(12) . . . . ?
C1_8 N3_4 C1_7 C2_7 64.89(16) . . . . ?
N3_4 C1_7 C2_7 C3_7 -166.72(12) . . . . ?
C1_7 C2_7 C3_7 C4_7 -174.39(13) . . . . ?
C1_6 N3_4 C1_8 C2_8 175.13(13) . . . . ?
C1_7 N3_4 C1_8 C2_8 54.64(17) . . . . ?
C1_5 N3_4 C1_8 C2_8 -63.82(16) . . . . ?
N3_4 C1_8 C2_8 C3_8 173.21(13) . . . . ?
C1_8 C2_8 C3_8 C4_8 177.94(15) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-Mes
_database_code_depnum_ccdc_archive 'CCDC 2394199'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.4e (K.Radacki, 2005-23)'
_audit_creation_date             2023-05-19
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C22 H21 B N2'
_chemical_formula_sum            'C22 H21 B N2'
_chemical_formula_weight         324.22
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   13.37660(10)
_cell_length_b                   12.64620(10)
_cell_length_c                   11.18210(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.6690(10)
_cell_angle_gamma                90
_cell_volume                     1769.85(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11554
_cell_measurement_theta_min      3.4550
_cell_measurement_theta_max      74.2170

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.1430
-2 -1 -2 0.1435
1 -1 -2 0.1363
2 -1 -2 0.1386
1 0 0 0.1277
0 1 2 0.1299
-2 2 1 0.1699
2 -2 -1 0.1557
-1 0 -1 0.1439
1 -2 -2 0.1310
-1 2 2 0.1565
1 0 1 0.1226
-1 2 0 0.1673
1 -2 0 0.1572
-1 2 -2 0.1318
1 -2 2 0.1219
0 1 0 0.1532
0 -1 0 0.1366
0 1 -1 0.1166
0 -1 1 0.1079
1 2 -1 0.1093
-1 -2 1 0.1157
0 0 1 0.1072
0 0 -1 0.1285
1 1 -1 0.1000
-2 -2 1 0.1277
-1 -1 2 0.1051
1 1 0 0.1235
-2 -2 -1 0.1456
-2 -1 2 0.1140
2 1 -2 0.1007
2 1 -1 0.1031
-2 -1 0 0.1382
-1 0 1 0.1173
2 1 2 0.1248
2 -1 0 0.1346

_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.895
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     15.00  68.00   0.50    0.05    --   58.60 -98.00 -80.00  106
  2  ω    -69.00 -17.00   0.50    0.05    --  -60.16  98.00  26.00  104
  3  ω    -79.00 -26.00   0.50    0.05    --  -69.71  98.00  26.00  106
  4  ω     28.00  81.00   0.50    0.05    --   71.26 -98.00 -80.00  106
  5  ω    -85.00 -33.00   0.50    0.05    --  -76.30  98.00  26.00  104
  6  ω     33.00  86.00   0.50    0.05    --   76.61 -98.00 -80.00  106
  7  ω     41.00  93.00   0.50    0.05    --   84.39 -98.00 -80.00  104
  8  ω     38.00 109.00   0.50    0.05    --   58.60  15.00 -90.00  142
  9  ω   -110.00 -31.00   0.50    0.05    --  -60.16 -15.00  90.00  158
 10  ω   -110.00 -31.00   0.50    0.05    --  -60.16 -15.00 -30.00  158
 11  ω     29.00  79.00   0.50    0.05    --   71.26 -95.00-150.00  100
 12  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00  30.00  122
 13  ω   -126.00 -40.00   0.50    0.05    --  -76.30 -15.00-180.00  172
 14  ω   -126.00 -40.00   0.50    0.05    --  -76.30 -15.00 -90.00  172
 15  ω     34.00  84.00   0.50    0.05    --   76.61 -95.00   0.00  100
 16  ω     34.00  84.00   0.50    0.05    --   76.61 -95.00 -30.00  100
 17  ω     42.00  92.00   0.50    0.05    --   84.39 -95.00   0.00  100
 18  ω     42.00  92.00   0.50    0.05    --   84.39 -95.00-150.00  100
 19  ω     42.00  92.00   0.50    0.05    --   84.39 -95.00  90.00  100
 20  ω     56.00 134.00   0.50    0.05    --   84.39  15.00-120.00  156
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0249538000
_diffrn_orient_matrix_UB_12      0.1024173000
_diffrn_orient_matrix_UB_13      -0.0587326000
_diffrn_orient_matrix_UB_21      0.1010067000
_diffrn_orient_matrix_UB_22      -0.0518491000
_diffrn_orient_matrix_UB_23      -0.0098512000
_diffrn_orient_matrix_UB_31      -0.0657167000
_diffrn_orient_matrix_UB_32      -0.0408188000
_diffrn_orient_matrix_UB_33      -0.1346642000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            17052
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.531
_diffrn_reflns_theta_max         74.567
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3491
_reflns_number_gt                3218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0504P)²+0.6184P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3491
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 0.32356(7) 0.42359(7) 0.37078(9) 0.0215(2) Uani 1 1 d . . . . .
C1 C 0.28281(9) 0.25361(9) 0.40970(11) 0.0254(2) Uani 1 1 d . . . . .
H1 H 0.292255 0.179705 0.402753 0.031 Uiso 1 1 calc R U . . .
B1 B 0.25050(9) 0.47183(10) 0.42184(12) 0.0215(3) Uani 1 1 d . . . . .
N2 N 0.33846(8) 0.31505(8) 0.36455(9) 0.0251(2) Uani 1 1 d . . . . .
C2 C 0.20803(9) 0.28551(9) 0.46939(10) 0.0231(2) Uani 1 1 d . . . . .
C15 C 0.26221(9) 0.66542(9) 0.50801(11) 0.0237(2) Uani 1 1 d . . . . .
C16 C 0.23733(9) 0.77254(9) 0.48766(11) 0.0261(3) Uani 1 1 d . . . . .
H16 H 0.262936 0.820353 0.557400 0.031 Uiso 1 1 calc R U . . .
C3 C 0.19161(8) 0.39440(9) 0.48009(10) 0.0219(2) Uani 1 1 d . . . . .
C17 C 0.17587(10) 0.81105(9) 0.36759(12) 0.0267(3) Uani 1 1 d . . . . .
C4 C 0.12025(9) 0.42599(9) 0.54069(11) 0.0251(2) Uani 1 1 d . . . . .
H4 H 0.107320 0.499135 0.548068 0.030 Uiso 1 1 calc R U . . .
C18 C 0.13679(9) 0.73942(9) 0.26721(11) 0.0253(2) Uani 1 1 d . . . . .
H18 H 0.093260 0.764320 0.185183 0.030 Uiso 1 1 calc R U . . .
C5 C 0.06881(9) 0.35209(10) 0.58952(11) 0.0277(3) Uani 1 1 d . . . . .
H5 H 0.021881 0.374698 0.631386 0.033 Uiso 1 1 calc R U . . .
C21 C 0.33314(10) 0.62900(10) 0.63913(11) 0.0299(3) Uani 1 1 d . . . . .
H21A H 0.318507 0.554470 0.650490 0.045 Uiso 1 1 calc R U . . .
H21B H 0.318748 0.671745 0.704362 0.045 Uiso 1 1 calc R U . . .
H21C H 0.408206 0.637160 0.647653 0.045 Uiso 1 1 calc R U . . .
C7 C 0.15363(9) 0.21068(9) 0.51707(11) 0.0259(2) Uani 1 1 d . . . . .
H7 H 0.163775 0.137231 0.507614 0.031 Uiso 1 1 calc R U . . .
C19 C 0.16027(9) 0.63204(9) 0.28476(11) 0.0226(2) Uani 1 1 d . . . . .
C6 C 0.08567(9) 0.24435(10) 0.57746(11) 0.0275(3) Uani 1 1 d . . . . .
H6 H 0.050049 0.193894 0.611121 0.033 Uiso 1 1 calc R U . . .
C22 C 0.15370(12) 0.92778(10) 0.34559(14) 0.0369(3) Uani 1 1 d . . . . .
H22A H 0.217717 0.963533 0.342441 0.055 Uiso 1 1 calc R U . . .
H22B H 0.134406 0.957204 0.415597 0.055 Uiso 1 1 calc R U . . .
H22C H 0.094562 0.938422 0.264452 0.055 Uiso 1 1 calc R U . . .
C8 C 0.38405(8) 0.48126(9) 0.30832(11) 0.0229(2) Uani 1 1 d . . . . .
C20 C 0.11639(9) 0.55709(9) 0.17338(11) 0.0276(3) Uani 1 1 d . . . . .
H20A H 0.065578 0.594776 0.100638 0.041 Uiso 1 1 calc R U . . .
H20B H 0.079953 0.498249 0.197845 0.041 Uiso 1 1 calc R U . . .
H20C H 0.175157 0.529594 0.149326 0.041 Uiso 1 1 calc R U . . .
C9 C 0.22506(8) 0.59370(9) 0.40575(10) 0.0214(2) Uani 1 1 d . . . . .
C10 C 0.43823(9) 0.57304(9) 0.36228(11) 0.0248(2) Uani 1 1 d . . . . .
H10 H 0.438387 0.596724 0.442967 0.030 Uiso 1 1 calc R U . . .
C11 C 0.49235(9) 0.63022(10) 0.29760(12) 0.0289(3) Uani 1 1 d . . . . .
H11 H 0.529301 0.693128 0.334328 0.035 Uiso 1 1 calc R U . . .
C12 C 0.49263(10) 0.59586(11) 0.17972(12) 0.0328(3) Uani 1 1 d . . . . .
H12 H 0.528413 0.635720 0.134978 0.039 Uiso 1 1 calc R U . . .
C13 C 0.44031(10) 0.50298(11) 0.12798(12) 0.0327(3) Uani 1 1 d . . . . .
H13 H 0.441246 0.478679 0.047995 0.039 Uiso 1 1 calc R U . . .
C14 C 0.38654(9) 0.44507(10) 0.19181(11) 0.0274(3) Uani 1 1 d . . . . .
H14 H 0.351580 0.381003 0.156159 0.033 Uiso 1 1 calc R U . . .


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 N2 1.3922(13) . ?
N1 B1 1.4308(15) . ?
N1 C8 1.4400(14) . ?
C1 N2 1.2954(15) . ?
C1 C2 1.4423(15) . ?
B1 C3 1.5381(16) . ?
B1 C9 1.5749(16) . ?
C2 C3 1.4061(15) . ?
C2 C7 1.4082(16) . ?
C15 C16 1.3944(16) . ?
C15 C9 1.4056(16) . ?
C15 C21 1.5100(16) . ?
C16 C17 1.3916(17) . ?
C3 C4 1.4095(15) . ?
C17 C18 1.3927(17) . ?
C17 C22 1.5087(16) . ?
C4 C5 1.3821(16) . ?
C18 C19 1.3920(16) . ?
C5 C6 1.3953(17) . ?
C7 C6 1.3774(17) . ?
C19 C9 1.4103(16) . ?
C19 C20 1.5094(16) . ?
C8 C10 1.3884(16) . ?
C8 C14 1.3923(16) . ?
C10 C11 1.3927(16) . ?
C11 C12 1.3893(18) . ?
C12 C13 1.3850(19) . ?
C13 C14 1.3876(17) . ?

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
N2 N1 B1 124.78(9) . . ?
N2 N1 C8 111.11(8) . . ?
B1 N1 C8 123.88(9) . . ?
N2 C1 C2 126.90(10) . . ?
N1 B1 C3 114.93(10) . . ?
N1 B1 C9 121.48(10) . . ?
C3 B1 C9 123.31(10) . . ?
C1 N2 N1 117.37(9) . . ?
C3 C2 C7 120.58(10) . . ?
C3 C2 C1 117.90(10) . . ?
C7 C2 C1 121.52(10) . . ?
C16 C15 C9 119.91(11) . . ?
C16 C15 C21 119.12(10) . . ?
C9 C15 C21 120.91(10) . . ?
C17 C16 C15 121.54(11) . . ?
C2 C3 C4 118.10(10) . . ?
C2 C3 B1 117.95(10) . . ?
C4 C3 B1 123.92(10) . . ?
C16 C17 C18 118.42(11) . . ?
C16 C17 C22 120.99(11) . . ?
C18 C17 C22 120.58(11) . . ?
C5 C4 C3 120.96(11) . . ?
C19 C18 C17 121.27(11) . . ?
C4 C5 C6 120.14(11) . . ?
C6 C7 C2 119.77(11) . . ?
C18 C19 C9 120.16(10) . . ?
C18 C19 C20 119.57(10) . . ?
C9 C19 C20 120.27(10) . . ?
C7 C6 C5 120.42(11) . . ?
C10 C8 C14 120.01(10) . . ?
C10 C8 N1 120.60(10) . . ?
C14 C8 N1 119.38(10) . . ?
C15 C9 C19 118.66(10) . . ?
C15 C9 B1 122.58(10) . . ?
C19 C9 B1 118.74(10) . . ?
C8 C10 C11 119.71(11) . . ?
C12 C11 C10 120.42(11) . . ?
C13 C12 C11 119.43(11) . . ?
C12 C13 C14 120.66(11) . . ?
C13 C14 C8 119.72(11) . . ?

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
N2 N1 B1 C3 3.90(15) . . . . ?
C8 N1 B1 C3 177.89(9) . . . . ?
N2 N1 B1 C9 -170.17(10) . . . . ?
C8 N1 B1 C9 3.82(16) . . . . ?
C2 C1 N2 N1 -1.68(17) . . . . ?
B1 N1 N2 C1 -0.81(16) . . . . ?
C8 N1 N2 C1 -175.46(10) . . . . ?
N2 C1 C2 C3 0.53(18) . . . . ?
N2 C1 C2 C7 -178.76(11) . . . . ?
C9 C15 C16 C17 0.10(17) . . . . ?
C21 C15 C16 C17 177.41(10) . . . . ?
C7 C2 C3 C4 0.58(16) . . . . ?
C1 C2 C3 C4 -178.73(10) . . . . ?
C7 C2 C3 B1 -177.89(10) . . . . ?
C1 C2 C3 B1 2.80(15) . . . . ?
N1 B1 C3 C2 -4.75(15) . . . . ?
C9 B1 C3 C2 169.20(10) . . . . ?
N1 B1 C3 C4 176.88(10) . . . . ?
C9 B1 C3 C4 -9.17(17) . . . . ?
C15 C16 C17 C18 1.59(17) . . . . ?
C15 C16 C17 C22 -177.21(11) . . . . ?
C2 C3 C4 C5 0.74(17) . . . . ?
B1 C3 C4 C5 179.11(11) . . . . ?
C16 C17 C18 C19 -1.53(16) . . . . ?
C22 C17 C18 C19 177.28(11) . . . . ?
C3 C4 C5 C6 -1.07(18) . . . . ?
C3 C2 C7 C6 -1.56(17) . . . . ?
C1 C2 C7 C6 177.72(11) . . . . ?
C17 C18 C19 C9 -0.22(16) . . . . ?
C17 C18 C19 C20 -179.94(10) . . . . ?
C2 C7 C6 C5 1.23(17) . . . . ?
C4 C5 C6 C7 0.07(18) . . . . ?
N2 N1 C8 C10 -138.41(10) . . . . ?
B1 N1 C8 C10 46.88(15) . . . . ?
N2 N1 C8 C14 42.57(13) . . . . ?
B1 N1 C8 C14 -132.14(12) . . . . ?
C16 C15 C9 C19 -1.85(15) . . . . ?
C21 C15 C9 C19 -179.10(10) . . . . ?
C16 C15 C9 B1 179.77(10) . . . . ?
C21 C15 C9 B1 2.52(16) . . . . ?
C18 C19 C9 C15 1.91(15) . . . . ?
C20 C19 C9 C15 -178.38(10) . . . . ?
C18 C19 C9 B1 -179.65(10) . . . . ?
C20 C19 C9 B1 0.06(15) . . . . ?
N1 B1 C9 C15 -108.11(12) . . . . ?
C3 B1 C9 C15 78.33(14) . . . . ?
N1 B1 C9 C19 73.51(14) . . . . ?
C3 B1 C9 C19 -100.05(13) . . . . ?
C14 C8 C10 C11 1.87(16) . . . . ?
N1 C8 C10 C11 -177.15(10) . . . . ?
C8 C10 C11 C12 -0.16(17) . . . . ?
C10 C11 C12 C13 -1.24(18) . . . . ?
C11 C12 C13 C14 0.94(19) . . . . ?
C12 C13 C14 C8 0.76(19) . . . . ?
C10 C8 C14 C13 -2.17(17) . . . . ?
N1 C8 C14 C13 176.86(10) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-OMe
_database_code_depnum_ccdc_archive 'CCDC 2394201'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.5c (K.Radacki, 2005-23)'
_audit_creation_date             2024-05-27
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C20 H17 B N2 O'
_chemical_formula_sum            'C20 H17 B N2 O'
_chemical_formula_weight         312.16
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'


_cell_length_a                   6.52650(10)
_cell_length_b                   9.4226(2)
_cell_length_c                   14.2267(2)
_cell_angle_alpha                106.0570(10)
_cell_angle_beta                 93.7340(10)
_cell_angle_gamma                100.512(2)
_cell_volume                     820.44(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11237
_cell_measurement_theta_min      3.2520
_cell_measurement_theta_max      73.4170

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0616
0 0 1 0.0577
-1 0 -2 0.0845
-2 0 1 0.1087
-1 0 -1 0.0894
1 0 0 0.1214
1 0 2 0.0791
0 -6 3 0.0379
2 3 -7 0.1142
3 -3 -6 0.1195
-1 -5 4 0.0411
0 6 -2 0.0441
-3 3 6 0.1055
-1 5 -6 0.0481
0 -5 7 0.0333
2 3 3 0.0679
-1 2 7 0.0597

_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.942
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 -60.00  100
  2  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00-180.00  100
  3  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00-150.00  100
  4  ω     46.00 133.00   0.50    0.05    --   82.26  15.00-150.00  174
  5  ω     46.00 133.00   0.50    0.05    --   82.26  15.00 -90.00  174
  6  ω     46.00 133.00   0.50    0.05    --   82.26  15.00-150.00  174
  7  ω   -118.00 -83.00   0.50    0.05    --  -70.00 -53.00 -65.02   70
  8  ω   -130.00 -91.00   0.50    0.05    --  -79.50 -39.00-103.45   78
  9  ω   -122.00 -87.00   0.50    0.05    --  -74.00 -52.00-152.80   70
 10  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00  91.95   70
 11  ω   -107.00 -72.00   0.50    0.05    --  -58.00 -50.00-132.88   70
 12  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -61.00 150.96   68
 13  ω   -121.00 -86.00   0.50    0.05    --  -74.00 -57.00  99.97   70
 14  ω   -124.00 -89.00   0.50    0.05    --  -78.00 -60.00 120.41   70
 15  ω   -125.00 -90.00   0.50    0.05    --  -78.00 -55.00  51.82   70
 16  ω   -122.00 -87.00   0.50    0.05    --  -74.00 -51.00 156.17   70
 17  ω     46.00 133.00   0.50    0.05    --   82.26  15.00  60.00  174
 18  ω     46.00 133.00   0.50    0.05    --   82.26  15.00 -30.00  174
 19  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00  60.00  122
 20  ω   -127.00 -92.00   0.50    0.05    --  -79.50 -55.00  13.76   70
 21  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00-120.00  122
 22  ω   -126.00 -93.00   0.50    0.05    --  -79.50-121.00-164.31   66
 23  ω    -97.00 -32.00   0.50    0.05    --  -78.00 114.00 -13.85  130
 24  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00 120.00  122
 25  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00-131.38   70
 26  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00  30.00  122
 27  ω    -48.00 -21.00   0.50    0.05    --  -14.00 136.00  -4.12   54
 28  ω    -92.00 -42.00   0.50    0.05    --  -76.36 112.00 150.00  100
 29  ω     30.00  56.00   0.50    0.05    --   18.00  60.00  96.13   52
 30  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00 120.00  122
 31  ω    -97.00 -32.00   0.50    0.05    --  -78.00 114.00 -45.64  130
 32  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -61.00-177.06   68
 33  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00-180.00  122
 34  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00-162.45   68
 35  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 150.00  100
 36  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00  90.00  122
 37  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 -30.00  100
 38  ω   -111.00 -76.00   0.50    0.05    --  -62.00 -48.00 107.33   70
 39  ω     16.00  66.00   0.50    0.05    --   58.74 -95.00 -60.00  100
 40  ω   -110.00 -75.00   0.50    0.05    --  -62.00 -51.00 -41.61   70
 41  ω   -126.00 -92.00   0.50    0.05    --  -79.50-122.00 117.93   68
 42  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 -90.00  100
 43  ω   -127.00 -92.00   0.50    0.05    --  -79.50 -54.00 -75.11   70
 44  ω   -107.00 -72.00   0.50    0.05    --  -58.00 -50.00  10.45   70
 45  ω     46.00 133.00   0.50    0.05    --   82.26  15.00  60.00  174
 46  ω     30.00  56.00   0.50    0.05    --   18.00  60.00-148.96   52
 47  ω     34.00  60.00   0.50    0.05    --   22.00  58.00 171.40   52
 48  ω     38.00 122.00   0.50    0.05    --   71.44  15.00 120.00  168
 49  ω   -118.00 -83.00   0.50    0.05    --  -70.00 -54.00  -4.71   70
 50  ω     30.00  56.00   0.50    0.05    --   18.00  60.00  10.52   52
 51  ω   -126.00 -93.00   0.50    0.05    --  -79.50-120.00  88.88   66
 52  ω   -126.00 -93.00   0.50    0.05    --  -79.50-121.00 169.89   66
 53  ω     38.00 122.00   0.50    0.05    --   71.44  15.00 120.00  168
 54  ω     30.00  60.00   0.50    0.05    --   18.00  59.00 -72.22   60
 55  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00  90.00  100
 56  ω   -126.00 -93.00   0.50    0.05    --  -79.50-120.00  22.77   66
 57  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00  60.00  100
 58  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 120.00  100
 59  ω   -111.00 -76.00   0.50    0.05    --  -62.00 -48.00  50.40   70
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.1928817000
_diffrn_orient_matrix_UB_12      -0.0473767000
_diffrn_orient_matrix_UB_13      -0.0787346000
_diffrn_orient_matrix_UB_21      -0.0167884000
_diffrn_orient_matrix_UB_22      -0.1660070000
_diffrn_orient_matrix_UB_23      -0.0018893000
_diffrn_orient_matrix_UB_31      -0.1450056000
_diffrn_orient_matrix_UB_32      0.0215701000
_diffrn_orient_matrix_UB_33      0.0817777000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            19256
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.257
_diffrn_reflns_theta_max         73.840
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3202
_reflns_number_gt                2811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       
;
 CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))
;
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0721P)²+0.1522P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_1 N 0.41818(16) 0.32353(11) 0.15927(7) 0.0242(2) Uani 1 1 d . . . . .
C1_1 C 0.3170(2) 0.49475(14) 0.08746(9) 0.0271(3) Uani 1 1 d . . . . .
H1_1 H 0.323749 0.540281 0.035609 0.033 Uiso 1 1 calc R U . . .
B1_1 B 0.3056(2) 0.36300(16) 0.24168(10) 0.0248(3) Uani 1 1 d . . . . .
N2_1 N 0.42643(17) 0.39202(12) 0.08386(8) 0.0272(3) Uani 1 1 d . . . . .
C2_1 C 0.1864(2) 0.54703(14) 0.16177(9) 0.0267(3) Uani 1 1 d . . . . .
C3_1 C 0.0712(2) 0.65743(15) 0.15579(10) 0.0328(3) Uani 1 1 d . . . . .
H3_1 H 0.078734 0.699022 0.102118 0.039 Uiso 1 1 calc R U . . .
C4_1 C -0.0524(2) 0.70479(17) 0.22802(11) 0.0397(3) Uani 1 1 d . . . . .
H4_1 H -0.130612 0.779144 0.224105 0.048 Uiso 1 1 calc R U . . .
C5_1 C -0.0635(2) 0.64389(17) 0.30727(11) 0.0379(3) Uani 1 1 d . . . . .
H5_1 H -0.149521 0.676858 0.356818 0.046 Uiso 1 1 calc R U . . .
C6_1 C 0.0499(2) 0.53617(15) 0.31374(10) 0.0307(3) Uani 1 1 d . . . . .
H6_1 H 0.042165 0.496493 0.368258 0.037 Uiso 1 1 calc R U . . .
C7_1 C 0.17648(19) 0.48430(13) 0.24114(9) 0.0257(3) Uani 1 1 d . . . . .
C1_2 C 0.54052(19) 0.20817(14) 0.14107(8) 0.0239(3) Uani 1 1 d . . . . .
C2_2 C 0.4554(2) 0.06420(14) 0.14564(9) 0.0272(3) Uani 1 1 d . . . . .
H2_2 H 0.317910 0.042243 0.163347 0.033 Uiso 1 1 calc R U . . .
C3_2 C 0.5724(2) -0.04730(15) 0.12421(9) 0.0302(3) Uani 1 1 d . . . . .
H3_2 H 0.514403 -0.145879 0.127081 0.036 Uiso 1 1 calc R U . . .
C4_2 C 0.7738(2) -0.01565(15) 0.09858(9) 0.0316(3) Uani 1 1 d . . . . .
H4_2 H 0.853466 -0.092249 0.083896 0.038 Uiso 1 1 calc R U . . .
C5_2 C 0.8578(2) 0.12822(16) 0.09456(9) 0.0305(3) Uani 1 1 d . . . . .
H5_2 H 0.995838 0.150346 0.077442 0.037 Uiso 1 1 calc R U . . .
C6_2 C 0.74161(19) 0.24035(15) 0.11536(9) 0.0272(3) Uani 1 1 d . . . . .
H6_2 H 0.799481 0.338689 0.112025 0.033 Uiso 1 1 calc R U . . .
C1_3 C 0.31616(19) 0.29023(13) 0.32820(9) 0.0250(3) Uani 1 1 d . . . . .
C2_3 C 0.1342(2) 0.20876(15) 0.35155(10) 0.0286(3) Uani 1 1 d . . . . .
H2_3 H 0.003798 0.195601 0.313058 0.034 Uiso 1 1 calc R U . . .
C3_3 C 0.1396(2) 0.14704(15) 0.42921(9) 0.0292(3) Uani 1 1 d . . . . .
H3_3 H 0.014897 0.089959 0.442364 0.035 Uiso 1 1 calc R U . . .
O1_3 O 0.31833(15) 0.10064(10) 0.56172(6) 0.0306(2) Uani 1 1 d . . . . .
C4_3 C 0.3284(2) 0.16895(13) 0.48789(9) 0.0258(3) Uani 1 1 d . . . . .
C5_3 C 0.5114(2) 0.25206(14) 0.46861(9) 0.0288(3) Uani 1 1 d . . . . .
H5_3 H 0.640157 0.269176 0.509301 0.035 Uiso 1 1 calc R U . . .
C6_3 C 0.5025(2) 0.30975(14) 0.38852(9) 0.0284(3) Uani 1 1 d . . . . .
H6_3 H 0.628182 0.364472 0.374489 0.034 Uiso 1 1 calc R U . . .
C7_3 C 0.4978(2) 0.13847(15) 0.63357(9) 0.0335(3) Uani 1 1 d . . . . .
H7A_3 H 0.471198 0.080907 0.680887 0.050 Uiso 1 1 calc R U . . .
H7B_3 H 0.525733 0.246773 0.668325 0.050 Uiso 1 1 calc R U . . .
H7C_3 H 0.619738 0.113728 0.600854 0.050 Uiso 1 1 calc R U . . .


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_1 N2_1 1.3958(13) . ?
N1_1 B1_1 1.4225(18) . ?
N1_1 C1_2 1.4402(16) . ?
C1_1 N2_1 1.2958(16) . ?
C1_1 C2_1 1.4386(18) . ?
C1_1 H1_1 0.9500 . ?
B1_1 C7_1 1.5402(18) . ?
B1_1 C1_3 1.5694(17) . ?
C2_1 C3_1 1.4074(18) . ?
C2_1 C7_1 1.4119(16) . ?
C3_1 C4_1 1.375(2) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.3997(19) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3797(19) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.4025(18) . ?
C6_1 H6_1 0.9500 . ?
C1_2 C6_2 1.3880(17) . ?
C1_2 C2_2 1.3897(17) . ?
C2_2 C3_2 1.3876(18) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.3889(19) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.3847(19) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3884(18) . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
C1_3 C6_3 1.3944(17) . ?
C1_3 C2_3 1.4037(17) . ?
C2_3 C3_3 1.3849(17) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.3910(18) . ?
C3_3 H3_3 0.9500 . ?
O1_3 C4_3 1.3747(13) . ?
O1_3 C7_3 1.4260(16) . ?
C4_3 C5_3 1.3915(18) . ?
C5_3 C6_3 1.3938(17) . ?
C5_3 H5_3 0.9500 . ?
C6_3 H6_3 0.9500 . ?
C7_3 H7A_3 0.9800 . ?
C7_3 H7B_3 0.9800 . ?
C7_3 H7C_3 0.9800 . ?

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
N2_1 N1_1 B1_1 124.65(10) . . ?
N2_1 N1_1 C1_2 109.88(9) . . ?
B1_1 N1_1 C1_2 125.46(10) . . ?
N2_1 C1_1 C2_1 126.79(11) . . ?
N2_1 C1_1 H1_1 116.6 . . ?
C2_1 C1_1 H1_1 116.6 . . ?
N1_1 B1_1 C7_1 115.40(11) . . ?
N1_1 B1_1 C1_3 122.22(11) . . ?
C7_1 B1_1 C1_3 122.37(11) . . ?
C1_1 N2_1 N1_1 117.46(10) . . ?
C3_1 C2_1 C7_1 120.71(12) . . ?
C3_1 C2_1 C1_1 121.15(11) . . ?
C7_1 C2_1 C1_1 118.14(11) . . ?
C4_1 C3_1 C2_1 119.69(12) . . ?
C4_1 C3_1 H3_1 120.2 . . ?
C2_1 C3_1 H3_1 120.2 . . ?
C3_1 C4_1 C5_1 120.26(13) . . ?
C3_1 C4_1 H4_1 119.9 . . ?
C5_1 C4_1 H4_1 119.9 . . ?
C6_1 C5_1 C4_1 120.29(13) . . ?
C6_1 C5_1 H5_1 119.9 . . ?
C4_1 C5_1 H5_1 119.9 . . ?
C5_1 C6_1 C7_1 121.07(12) . . ?
C5_1 C6_1 H6_1 119.5 . . ?
C7_1 C6_1 H6_1 119.5 . . ?
C6_1 C7_1 C2_1 117.98(11) . . ?
C6_1 C7_1 B1_1 124.55(11) . . ?
C2_1 C7_1 B1_1 117.48(11) . . ?
C6_2 C1_2 C2_2 120.18(12) . . ?
C6_2 C1_2 N1_1 119.42(11) . . ?
C2_2 C1_2 N1_1 120.36(11) . . ?
C3_2 C2_2 C1_2 119.66(12) . . ?
C3_2 C2_2 H2_2 120.2 . . ?
C1_2 C2_2 H2_2 120.2 . . ?
C2_2 C3_2 C4_2 120.39(12) . . ?
C2_2 C3_2 H3_2 119.8 . . ?
C4_2 C3_2 H3_2 119.8 . . ?
C5_2 C4_2 C3_2 119.61(12) . . ?
C5_2 C4_2 H4_2 120.2 . . ?
C3_2 C4_2 H4_2 120.2 . . ?
C4_2 C5_2 C6_2 120.44(12) . . ?
C4_2 C5_2 H5_2 119.8 . . ?
C6_2 C5_2 H5_2 119.8 . . ?
C1_2 C6_2 C5_2 119.72(12) . . ?
C1_2 C6_2 H6_2 120.1 . . ?
C5_2 C6_2 H6_2 120.1 . . ?
C6_3 C1_3 C2_3 116.88(11) . . ?
C6_3 C1_3 B1_1 122.09(11) . . ?
C2_3 C1_3 B1_1 120.94(11) . . ?
C3_3 C2_3 C1_3 121.75(12) . . ?
C3_3 C2_3 H2_3 119.1 . . ?
C1_3 C2_3 H2_3 119.1 . . ?
C2_3 C3_3 C4_3 119.75(11) . . ?
C2_3 C3_3 H3_3 120.1 . . ?
C4_3 C3_3 H3_3 120.1 . . ?
C4_3 O1_3 C7_3 117.72(10) . . ?
O1_3 C4_3 C3_3 115.34(11) . . ?
O1_3 C4_3 C5_3 124.37(11) . . ?
C3_3 C4_3 C5_3 120.27(11) . . ?
C4_3 C5_3 C6_3 118.79(12) . . ?
C4_3 C5_3 H5_3 120.6 . . ?
C6_3 C5_3 H5_3 120.6 . . ?
C5_3 C6_3 C1_3 122.52(11) . . ?
C5_3 C6_3 H6_3 118.7 . . ?
C1_3 C6_3 H6_3 118.7 . . ?
O1_3 C7_3 H7A_3 109.5 . . ?
O1_3 C7_3 H7B_3 109.5 . . ?
H7A_3 C7_3 H7B_3 109.5 . . ?
O1_3 C7_3 H7C_3 109.5 . . ?
H7A_3 C7_3 H7C_3 109.5 . . ?
H7B_3 C7_3 H7C_3 109.5 . . ?

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
N2_1 N1_1 B1_1 C7_1 3.52(17) . . . . ?
C1_2 N1_1 B1_1 C7_1 -176.66(10) . . . . ?
N2_1 N1_1 B1_1 C1_3 -175.27(10) . . . . ?
C1_2 N1_1 B1_1 C1_3 4.55(19) . . . . ?
C2_1 C1_1 N2_1 N1_1 0.15(19) . . . . ?
B1_1 N1_1 N2_1 C1_1 -2.81(17) . . . . ?
C1_2 N1_1 N2_1 C1_1 177.35(10) . . . . ?
N2_1 C1_1 C2_1 C3_1 -178.48(12) . . . . ?
N2_1 C1_1 C2_1 C7_1 1.4(2) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.0(2) . . . . ?
C1_1 C2_1 C3_1 C4_1 179.91(13) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.1(2) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.2(2) . . . . ?
C4_1 C5_1 C6_1 C7_1 -0.7(2) . . . . ?
C5_1 C6_1 C7_1 C2_1 0.77(19) . . . . ?
C5_1 C6_1 C7_1 B1_1 -179.08(12) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.45(18) . . . . ?
C1_1 C2_1 C7_1 C6_1 179.65(11) . . . . ?
C3_1 C2_1 C7_1 B1_1 179.41(11) . . . . ?
C1_1 C2_1 C7_1 B1_1 -0.49(17) . . . . ?
N1_1 B1_1 C7_1 C6_1 178.12(11) . . . . ?
C1_3 B1_1 C7_1 C6_1 -3.09(19) . . . . ?
N1_1 B1_1 C7_1 C2_1 -1.73(17) . . . . ?
C1_3 B1_1 C7_1 C2_1 177.06(11) . . . . ?
N2_1 N1_1 C1_2 C6_2 47.45(14) . . . . ?
B1_1 N1_1 C1_2 C6_2 -132.39(13) . . . . ?
N2_1 N1_1 C1_2 C2_2 -130.21(11) . . . . ?
B1_1 N1_1 C1_2 C2_2 49.95(17) . . . . ?
C6_2 C1_2 C2_2 C3_2 -0.11(18) . . . . ?
N1_1 C1_2 C2_2 C3_2 177.53(10) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.20(18) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.05(19) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.39(19) . . . . ?
C2_2 C1_2 C6_2 C5_2 -0.23(18) . . . . ?
N1_1 C1_2 C6_2 C5_2 -177.89(10) . . . . ?
C4_2 C5_2 C6_2 C1_2 0.48(18) . . . . ?
N1_1 B1_1 C1_3 C6_3 63.32(17) . . . . ?
C7_1 B1_1 C1_3 C6_3 -115.39(14) . . . . ?
N1_1 B1_1 C1_3 C2_3 -120.18(14) . . . . ?
C7_1 B1_1 C1_3 C2_3 61.11(17) . . . . ?
C6_3 C1_3 C2_3 C3_3 -1.65(19) . . . . ?
B1_1 C1_3 C2_3 C3_3 -178.32(12) . . . . ?
C1_3 C2_3 C3_3 C4_3 1.8(2) . . . . ?
C7_3 O1_3 C4_3 C3_3 -170.25(11) . . . . ?
C7_3 O1_3 C4_3 C5_3 11.34(18) . . . . ?
C2_3 C3_3 C4_3 O1_3 -178.70(11) . . . . ?
C2_3 C3_3 C4_3 C5_3 -0.22(19) . . . . ?
O1_3 C4_3 C5_3 C6_3 177.00(11) . . . . ?
C3_3 C4_3 C5_3 C6_3 -1.34(19) . . . . ?
C4_3 C5_3 C6_3 C1_3 1.45(19) . . . . ?
C2_3 C1_3 C6_3 C5_3 0.02(19) . . . . ?
B1_1 C1_3 C6_3 C5_3 176.65(12) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-OTMS
_database_code_depnum_ccdc_archive 'CCDC 2394202'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.4c (K.Radacki, 2005-23)'
_audit_creation_date             2023-05-08
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C16 H19 B N2 O Si'
_chemical_formula_sum            'C16 H19 B N2 O Si'
_chemical_formula_weight         294.23
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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'


_cell_length_a                   8.8219(2)
_cell_length_b                   9.3512(2)
_cell_length_c                   10.4070(2)
_cell_angle_alpha                84.139(2)
_cell_angle_beta                 68.542(2)
_cell_angle_gamma                74.660(2)
_cell_volume                     770.54(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19191
_cell_measurement_theta_min      4.8900
_cell_measurement_theta_max      73.9790

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 0 0.0838
0 -1 2 0.0848
1 1 2 0.0746
1 2 0 0.0830
-1 -2 -2 0.0923
0 -1 -2 0.0994
1 1 -1 0.1018
0 1 2 0.0859
2 1 -2 0.0975
-2 -1 2 0.0917
0 1 1 0.0752
1 -1 -2 0.0926
2 1 -1 0.0874
-2 -1 0 0.0756
2 -1 -1 0.0775
2 1 0 0.0685
0 2 1 0.0713
-2 1 0 0.0552
2 1 1 0.0577
-2 -1 -1 0.0493
-1 2 0 0.0539
-2 0 -1 0.0331
2 0 1 0.0615
0 1 0 0.0657
-1 0 -1 0.0462
-1 0 -2 0.0632

_shelx_estimated_absorpt_T_min   0.777
_shelx_estimated_absorpt_T_max   0.890
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -82.00 -14.00   0.50    0.05    --  -60.16 118.00 133.00  136
  2  ω    -92.00 -24.00   0.50    0.05    --  -69.71 118.00 133.00  136
  3  ω    -97.00 -30.00   0.50    0.05    --  -76.30 118.00 133.00  134
  4  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00 120.00  122
  5  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00  90.00  122
  6  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00  60.00  122
  7  ω   -105.00 -33.00   0.50    0.05    --  -79.50 135.00   6.21  144
  8  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00-180.00  122
  9  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00-120.00  122
 10  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00 -90.00  122
 11  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00 -60.00  122
 12  ω    -92.00 -31.00   0.50    0.05    --  -76.30 112.00   0.00  122
 13  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -61.00  66.91   68
 14  ω   -124.00 -89.00   0.50    0.05    --  -78.00 -61.00  93.52   70
 15  ω   -120.00 -86.00   0.50    0.05    --  -74.00 -60.00 175.03   68
 16  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00 128.53   68
 17  ω   -120.00 -86.00   0.50    0.05    --  -74.00 -59.00  53.17   68
 18  ω   -121.00 -86.00   0.50    0.05    --  -74.00 -58.00  26.03   70
 19  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -58.00  21.53   70
 20  ω   -117.00 -84.00   0.50    0.05    --  -70.00 -57.00 135.72   66
 21  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00  10.69   70
 22  ω   -121.00 -86.00   0.50    0.05    --  -74.00 -56.00 -35.55   70
 23  ω   -126.00 -92.00   0.50    0.05    --  -79.50 -57.00 -42.60   68
 24  ω   -121.00 -86.00   0.50    0.05    --  -74.00 -56.00 -82.71   70
 25  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00 -92.97   70
 26  ω   -122.00 -87.00   0.50    0.05    --  -74.00 -52.00 -72.41   70
 27  ω   -127.00 -92.00   0.50    0.05    --  -79.50 -54.00-115.57   70
 28  ω   -127.00 -92.00   0.50    0.05    --  -79.50 -55.00-136.00   70
 29  ω   -127.00 -92.00   0.50    0.05    --  -79.50 -53.00-159.32   70
 30  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00-179.22   70
 31  ω   -121.00 -86.00   0.50    0.05    --  -74.00 -57.00-165.67   70
 32  ω   -106.00 -71.00   0.50    0.05    --  -58.00 -51.00-155.84   70
 33  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00 -64.63   70
 34  ω   -110.00 -75.00   0.50    0.05    --  -62.00 -51.00 -33.44   70
 35  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -50.00  32.86   70
 36  ω   -103.00 -67.00   0.50    0.05    --  -54.00 -46.00  34.50   72
 37  ω   -129.00 -92.00   0.50    0.05    --  -79.50 -44.00  85.25   74
 38  ω   -130.00 -92.00   0.50    0.05    --  -79.50 -42.00  92.02   76
 39  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -49.00 149.38   70
 40  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -49.00 130.51   70
 41  ω   -130.00 -90.00   0.50    0.05    --  -79.50 -38.00 105.05   80
 42  ω   -125.00 -85.00   0.50    0.05    --  -74.00 -34.00  94.62   80
 43  ω   -130.00 -91.00   0.50    0.05    --  -79.50 -41.00  10.54   78
 44  ω   -130.00 -91.00   0.50    0.05    --  -79.50 -40.00 -38.24   78
 45  ω   -131.00 -90.00   0.50    0.05    --  -79.50 -35.00-131.30   82
 46  ω   -125.00 -94.00   0.50    0.05    --  -79.50-119.00  71.89   62
 47  ω   -127.00 -89.00   0.50    0.05    --  -79.50-129.00 126.29   76
 48  ω    -54.00 -27.00   0.50    0.05    --  -14.00 -53.00 178.79   54
 49  ω    -54.00 -27.00   0.50    0.05    --  -14.00 -53.00 112.13   54
 50  ω    -82.00 -47.00   0.50    0.05    --  -34.00 -52.00 100.93   70
 51  ω    -54.00 -27.00   0.50    0.05    --  -14.00 -53.00 -13.23   54
 52  ω    -54.00 -26.00   0.50    0.05    --  -14.00 -55.00 -48.62   56
 53  ω    -86.00 -51.00   0.50    0.05    --  -38.00 -52.00 -94.53   70
 54  ω   -126.00 -91.00   0.50    0.05    --  -79.50-125.00-138.86   70
 55  ω    -78.00 -43.00   0.50    0.05    --  -30.00 -52.00-120.22   70
 56  ω    -75.00 -40.00   0.50    0.05    --  -26.00 -49.00 -90.03   70
 57  ω    -91.00 -56.00   0.50    0.05    --  -42.00 -48.00 -29.88   70
 58  ω    -71.00 -36.00   0.50    0.05    --  -22.00 -49.00  41.57   70
 59  ω    -99.00 -64.00   0.50    0.05    --  -50.00 -48.00  73.57   70
 60  ω    -99.00 -64.00   0.50    0.05    --  -50.00 -47.00 138.20   70
 61  ω    -74.00 -39.00   0.50    0.05    --  -26.00 -51.00 149.04   70
 62  ω     15.00  81.00   0.50    0.05    --   58.60-118.00  47.00  132
 63  ω     25.00  93.00   0.50    0.05    --   71.26-118.00  47.00  136
 64  ω     37.00  97.00   0.50    0.05    --   82.35-118.00  47.00  120
 65  ω     37.00  93.00   0.50    0.05    --   82.35-112.00 120.00  112
 66  ω     42.00  93.00   0.50    0.05    --   85.25 -97.00  40.11  102
 67  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00  60.00  100
 68  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00 -60.00  100
 69  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00-120.00  100
 70  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00-150.00  100
 71  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00-180.00  100
 72  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00 -30.00  100
 73  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00 -90.00  100
 74  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00   0.00  100
 75  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00 120.00  100
 76  ω     40.00  90.00   0.50    0.05    --   82.35 -95.00 150.00  100
 77  ω     46.00 133.00   0.50    0.05    --   82.35  15.00 150.00  174
 78  ω     46.00 133.00   0.50    0.05    --   82.35  15.00  30.00  174
 79  ω     46.00 133.00   0.50    0.05    --   82.35  15.00 -30.00  174
 80  ω     46.00 133.00   0.50    0.05    --   82.35  15.00 -60.00  174
 81  ω     46.00 133.00   0.50    0.05    --   82.35  15.00-120.00  174
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.1713016000
_diffrn_orient_matrix_UB_12      -0.0968467000
_diffrn_orient_matrix_UB_13      -0.0006830000
_diffrn_orient_matrix_UB_21      -0.0754754000
_diffrn_orient_matrix_UB_22      -0.0216398000
_diffrn_orient_matrix_UB_23      0.1574060000
_diffrn_orient_matrix_UB_31      -0.0492105000
_diffrn_orient_matrix_UB_32      -0.1390556000
_diffrn_orient_matrix_UB_33      -0.0228569000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            23656
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.565
_diffrn_reflns_theta_max         74.105
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3034
_reflns_number_gt                2980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0395P)²+0.3155P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3034
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.039
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Si1 Si 0.37867(4) 0.19292(3) 0.74802(3) 0.01552(10) Uani 1 1 d . . . . .
C1 C 0.60713(14) 0.69705(12) 0.77264(12) 0.0182(2) Uani 1 1 d . . . . .
H1 H 0.657747 0.775433 0.771121 0.022 Uiso 1 1 calc R U . . .
O1 O 0.37213(10) 0.36596(9) 0.77226(8) 0.01847(18) Uani 1 1 d . . . . .
N1 N 0.40826(12) 0.61549(10) 0.72704(10) 0.0158(2) Uani 1 1 d . . . . .
B1 B 0.45763(16) 0.46610(14) 0.77532(12) 0.0161(2) Uani 1 1 d . . . . .
N2 N 0.48195(12) 0.72886(10) 0.72943(10) 0.0181(2) Uani 1 1 d . . . . .
C2 C 0.67823(14) 0.55529(12) 0.82294(11) 0.0168(2) Uani 1 1 d . . . . .
C7 C 0.81452(14) 0.53797(13) 0.86751(12) 0.0191(2) Uani 1 1 d . . . . .
H7 H 0.863282 0.618731 0.861689 0.023 Uiso 1 1 calc R U . . .
C5 C 0.80546(15) 0.28423(13) 0.92735(12) 0.0212(2) Uani 1 1 d . . . . .
H5 H 0.848843 0.191475 0.963412 0.025 Uiso 1 1 calc R U . . .
C6 C 0.87700(15) 0.40309(13) 0.91972(12) 0.0212(2) Uani 1 1 d . . . . .
H6 H 0.968646 0.390885 0.950503 0.025 Uiso 1 1 calc R U . . .
C4 C 0.67216(14) 0.30071(13) 0.88284(11) 0.0184(2) Uani 1 1 d . . . . .
H4 H 0.624584 0.219087 0.889066 0.022 Uiso 1 1 calc R U . . .
C3 C 0.60582(14) 0.43668(12) 0.82839(11) 0.0161(2) Uani 1 1 d . . . . .
C13 C 0.15787(14) 0.80550(12) 0.72548(12) 0.0186(2) Uani 1 1 d . . . . .
H13 H 0.169702 0.859426 0.792376 0.022 Uiso 1 1 calc R U . . .
C9 C 0.25063(14) 0.58977(13) 0.58244(12) 0.0189(2) Uani 1 1 d . . . . .
H9 H 0.326382 0.496744 0.550564 0.023 Uiso 1 1 calc R U . . .
C8 C 0.27004(14) 0.66929(12) 0.67891(11) 0.0165(2) Uani 1 1 d . . . . .
C12 C 0.02889(15) 0.86241(13) 0.67421(12) 0.0214(2) Uani 1 1 d . . . . .
H12 H -0.046415 0.955787 0.705436 0.026 Uiso 1 1 calc R U . . .
C10 C 0.11977(15) 0.64700(14) 0.53276(12) 0.0217(2) Uani 1 1 d . . . . .
H10 H 0.105888 0.592141 0.467635 0.026 Uiso 1 1 calc R U . . .
C11 C 0.00928(15) 0.78377(14) 0.57766(12) 0.0223(3) Uani 1 1 d . . . . .
H11 H -0.078877 0.823032 0.542557 0.027 Uiso 1 1 calc R U . . .
C14 C 0.59526(15) 0.08856(13) 0.64901(13) 0.0241(3) Uani 1 1 d . . . . .
H14A H 0.592395 -0.008097 0.622675 0.036 Uiso 1 1 calc R U . . .
H14B H 0.664992 0.073947 0.706332 0.036 Uiso 1 1 calc R U . . .
H14C H 0.642781 0.144710 0.565720 0.036 Uiso 1 1 calc R U . . .
C15 C 0.29890(15) 0.10311(13) 0.91989(12) 0.0218(2) Uani 1 1 d . . . . .
H15A H 0.314207 -0.002876 0.907306 0.033 Uiso 1 1 calc R U . . .
H15B H 0.179231 0.149258 0.965568 0.033 Uiso 1 1 calc R U . . .
H15C H 0.361386 0.115795 0.977033 0.033 Uiso 1 1 calc R U . . .
C16 C 0.24337(16) 0.19810(13) 0.64605(12) 0.0222(2) Uani 1 1 d . . . . .
H16A H 0.295370 0.234322 0.552543 0.033 Uiso 1 1 calc R U . . .
H16B H 0.132780 0.264622 0.690539 0.033 Uiso 1 1 calc R U . . .
H16C H 0.230462 0.098091 0.641172 0.033 Uiso 1 1 calc R U . . .


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
Si1 O1 1.6458(8) . ?
Si1 C16 1.8544(12) . ?
Si1 C14 1.8557(12) . ?
Si1 C15 1.8668(12) . ?
C1 N2 1.2933(15) . ?
C1 C2 1.4433(15) . ?
O1 B1 1.3580(15) . ?
N1 N2 1.3889(13) . ?
N1 C8 1.4359(14) . ?
N1 B1 1.4452(15) . ?
B1 C3 1.5481(16) . ?
C2 C7 1.4059(16) . ?
C2 C3 1.4061(16) . ?
C7 C6 1.3789(16) . ?
C5 C4 1.3818(16) . ?
C5 C6 1.3987(17) . ?
C4 C3 1.4079(15) . ?
C13 C12 1.3887(16) . ?
C13 C8 1.3946(16) . ?
C9 C8 1.3914(16) . ?
C9 C10 1.3927(16) . ?
C12 C11 1.3877(18) . ?
C10 C11 1.3905(18) . ?

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
O1 Si1 C16 107.03(5) . . ?
O1 Si1 C14 111.39(5) . . ?
C16 Si1 C14 108.52(6) . . ?
O1 Si1 C15 108.69(5) . . ?
C16 Si1 C15 111.18(6) . . ?
C14 Si1 C15 110.01(6) . . ?
N2 C1 C2 127.01(10) . . ?
B1 O1 Si1 147.58(8) . . ?
N2 N1 C8 110.87(9) . . ?
N2 N1 B1 124.23(9) . . ?
C8 N1 B1 124.78(9) . . ?
O1 B1 N1 118.86(10) . . ?
O1 B1 C3 125.96(10) . . ?
N1 B1 C3 115.17(10) . . ?
C1 N2 N1 117.78(9) . . ?
C7 C2 C3 121.22(10) . . ?
C7 C2 C1 120.45(10) . . ?
C3 C2 C1 118.33(10) . . ?
C6 C7 C2 119.62(11) . . ?
C4 C5 C6 120.49(11) . . ?
C7 C6 C5 120.00(11) . . ?
C5 C4 C3 120.98(11) . . ?
C2 C3 C4 117.69(10) . . ?
C2 C3 B1 117.41(10) . . ?
C4 C3 B1 124.90(10) . . ?
C12 C13 C8 120.08(11) . . ?
C8 C9 C10 119.78(11) . . ?
C9 C8 C13 119.71(10) . . ?
C9 C8 N1 120.71(10) . . ?
C13 C8 N1 119.53(10) . . ?
C11 C12 C13 120.43(11) . . ?
C11 C10 C9 120.56(11) . . ?
C12 C11 C10 119.42(11) . . ?

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
C16 Si1 O1 B1 -138.05(14) . . . . ?
C14 Si1 O1 B1 -19.58(16) . . . . ?
C15 Si1 O1 B1 101.78(15) . . . . ?
Si1 O1 B1 N1 144.17(11) . . . . ?
Si1 O1 B1 C3 -36.6(2) . . . . ?
N2 N1 B1 O1 177.69(9) . . . . ?
C8 N1 B1 O1 2.02(16) . . . . ?
N2 N1 B1 C3 -1.59(15) . . . . ?
C8 N1 B1 C3 -177.27(9) . . . . ?
C2 C1 N2 N1 -1.66(17) . . . . ?
C8 N1 N2 C1 179.03(9) . . . . ?
B1 N1 N2 C1 2.83(16) . . . . ?
N2 C1 C2 C7 -179.57(11) . . . . ?
N2 C1 C2 C3 -0.72(18) . . . . ?
C3 C2 C7 C6 -1.08(17) . . . . ?
C1 C2 C7 C6 177.75(10) . . . . ?
C2 C7 C6 C5 0.37(17) . . . . ?
C4 C5 C6 C7 0.02(18) . . . . ?
C6 C5 C4 C3 0.28(18) . . . . ?
C7 C2 C3 C4 1.34(16) . . . . ?
C1 C2 C3 C4 -177.51(10) . . . . ?
C7 C2 C3 B1 -179.27(10) . . . . ?
C1 C2 C3 B1 1.88(15) . . . . ?
C5 C4 C3 C2 -0.94(16) . . . . ?
C5 C4 C3 B1 179.72(11) . . . . ?
O1 B1 C3 C2 179.96(10) . . . . ?
N1 B1 C3 C2 -0.81(15) . . . . ?
O1 B1 C3 C4 -0.70(18) . . . . ?
N1 B1 C3 C4 178.53(10) . . . . ?
C10 C9 C8 C13 0.24(16) . . . . ?
C10 C9 C8 N1 -177.29(10) . . . . ?
C12 C13 C8 C9 -0.94(17) . . . . ?
C12 C13 C8 N1 176.61(10) . . . . ?
N2 N1 C8 C9 135.11(10) . . . . ?
B1 N1 C8 C9 -48.71(15) . . . . ?
N2 N1 C8 C13 -42.42(13) . . . . ?
B1 N1 C8 C13 133.76(11) . . . . ?
C8 C13 C12 C11 0.75(17) . . . . ?
C8 C9 C10 C11 0.67(17) . . . . ?
C13 C12 C11 C10 0.16(18) . . . . ?
C9 C10 C11 C12 -0.87(17) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-Me
_database_code_depnum_ccdc_archive 'CCDC 2394198'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.4u (K.Radacki, 2005-23)'
_audit_creation_date             2024-04-16
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C14 H13 B N2'
_chemical_formula_sum            'C14 H13 B N2'
_chemical_formula_weight         220.07
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'


_cell_length_a                   23.6005(2)
_cell_length_b                   6.89970(10)
_cell_length_c                   14.16730(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2306.95(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30291
_cell_measurement_theta_min      3.6090
_cell_measurement_theta_max      74.2620

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.690
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -9 0.1057
0 -1 9 0.0975
4 1 -2 0.2757
4 0 4 0.2895
-4 -1 2 0.3818
-4 0 -2 0.3825
0 -15 -2 0.0230
0 15 2 0.0175

_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.977
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω    -36.00 -10.00   0.50    0.23    --  -14.00 121.00-161.97   52
  2  ω    -87.00 -16.00   0.50    0.23    --  -61.61 127.00 -94.00  142
  3  ω   -101.00 -31.00   0.50    0.23    --  -76.35 127.00 -94.00  140
  4  ω    -97.00 -35.00   0.50    0.23    --  -79.50 116.00 -51.48  124
  5  ω    -97.00 -26.00   0.50    0.23    --  -71.68 127.00 -94.00  142
  6  ω    -97.00 -36.00   0.50    0.23    --  -79.50 114.00-150.47  122
  7  ω    -97.00 -36.00   0.50    0.23    --  -79.50 114.00-109.83  122
  8  ω    -97.00 -36.00   0.50    0.23    --  -79.50 115.00 -12.34  122
  9  ω    -97.00 -36.00   0.50    0.23    --  -79.50 114.00  23.67  122
 10  ω    -85.00 -17.00   0.50    0.23    --  -61.61 125.00  30.00  136
 11  ω    -97.00 -36.00   0.50    0.23    --  -79.50 114.00  55.79  122
 12  ω    -97.00 -36.00   0.50    0.23    --  -79.50 115.00 136.25  122
 13  ω    -92.00 -33.00   0.50    0.23    --  -76.35 112.00  60.00  118
 14  ω    -97.00 -36.00   0.50    0.23    --  -79.50 114.00  55.79  122
 15  ω    -92.00 -33.00   0.50    0.23    --  -76.35 112.00-150.00  118
 16  ω     28.00  56.00   0.50    0.23    --   14.00  60.00-120.71   56
 17  ω     33.00  60.00   0.50    0.23    --   18.00  56.00-167.31   54
 18  ω     58.00  89.00   0.50    0.23    --   42.00  51.00-147.25   62
 19  ω     32.00  60.00   0.50    0.23    --   18.00  58.00 -70.84   56
 20  ω     38.00  69.00   0.50    0.23    --   22.00  51.00  -7.49   62
 21  ω     28.00  56.00   0.50    0.23    --   14.00  60.00  39.51   56
 22  ω     32.00  60.00   0.50    0.23    --   18.00  59.00  78.85   56
 23  ω     54.00  85.00   0.50    0.23    --   38.00  49.00  32.36   62
 24  ω     54.00 128.00   0.50    0.23    --   80.28  15.00 120.00  148
 25  ω     54.00 128.00   0.50    0.23    --   80.28  15.00-180.00  148
 26  ω     54.00 128.00   0.50    0.23    --   80.28  15.00-180.00  148
 27  ω     21.00  86.00   0.50    0.23    --   60.16-127.00-169.00  130
 28  ω     28.00  99.00   0.50    0.23    --   73.63-127.00-169.00  142
 29  ω     28.00  99.00   0.50    0.23    --   73.63-127.00-169.00  142
 30  ω     35.00 101.00   0.50    0.23    --   80.28-127.00-169.00  132
 31  ω     40.00  86.00   0.50    0.23    --   80.28 -95.00-150.00   92
 32  ω     42.00  91.00   0.50    0.23    --   83.50 -99.00-103.23   98
 33  ω     19.00  66.00   0.50    0.23    --   60.16 -95.00   0.00   94
 34  ω     33.00  79.00   0.50    0.23    --   73.63 -95.00  30.00   92
 35  ω     40.00  86.00   0.50    0.23    --   80.28 -95.00  30.00   92
 36  ω     40.00  86.00   0.50    0.23    --   80.28 -95.00 120.00   92
 37  ω    -54.00 -28.00   0.50    0.23    --  -14.00 -57.00  80.97   52
 38  ω    -96.00 -65.00   0.50    0.23    --  -50.00 -52.00 121.80   62
 39  ω    -90.00 -57.00   0.50    0.23    --  -42.00 -44.00  33.07   66
 40  ω    -96.00 -65.00   0.50    0.23    --  -50.00 -52.00-114.29   62
 41  ω    -97.00 -66.00   0.50    0.23    --  -50.00 -48.00-152.79   62
 42  ω   -124.00 -56.00   0.50    0.23    --  -76.35 -15.00 -90.00  136
 43  ω   -125.00 -94.00   0.50    0.23    --  -79.50 -55.00 -76.60   62
 44  ω   -125.00 -95.00   0.50    0.23    --  -79.50 -54.00-146.43   60
 45  ω   -104.00 -73.00   0.50    0.23    --  -58.00 -52.00 -93.51   62
 46  ω   -122.00 -94.00   0.50    0.23    --  -79.50 -64.00 -32.32   56
 47  ω   -104.00 -74.00   0.50    0.23    --  -58.00 -51.00 -42.34   60
 48  ω   -126.00 -95.00   0.50    0.23    --  -79.50 -52.00  21.02   62
 49  ω   -126.00 -96.00   0.50    0.23    --  -79.50 -49.00-105.77   60
 50  ω   -104.00 -73.00   0.50    0.23    --  -58.00 -52.00  53.63   62
 51  ω   -119.00 -89.00   0.50    0.23    --  -74.00 -56.00  65.40   60
 52  ω   -109.00 -78.00   0.50    0.23    --  -62.00 -47.00  95.82   62
 53  ω   -126.00 -96.00   0.50    0.23    --  -79.50 -49.00 107.23   60
 54  ω   -126.00 -96.00   0.50    0.23    --  -79.50 -49.00 148.09   60
 55  ω   -109.00 -78.00   0.50    0.23    --  -62.00 -49.00 179.93   62
 56  ω   -114.00 -81.00   0.50    0.23    --  -66.00 -45.00 148.40   66
 57  ω   -105.00 -74.00   0.50    0.23    --  -58.00 -47.00  16.54   62
 58  ω   -123.00 -87.00   0.50    0.23    --  -74.00 -35.00 -10.16   72
 59  ω   -123.00 -87.00   0.50    0.23    --  -74.00 -35.00-157.38   72
 60  ω   -128.00 -94.00   0.50    0.23    --  -79.50 -42.00-126.29   68
 61  ω   -127.00 -92.00   0.50    0.23    --  -78.00 -37.00-172.31   70
 62  ω   -110.00 -78.00   0.50    0.23    --  -62.00 -46.00 -61.60   64
 63  ω   -128.00 -65.00   0.50    0.23    --  -79.50 -17.00 -46.16  126
 64  ω   -125.00 -90.00   0.50    0.23    --  -79.50-126.00  58.19   70
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.1155792000
_diffrn_orient_matrix_UB_12      -0.0437749000
_diffrn_orient_matrix_UB_13      -0.0578060000
_diffrn_orient_matrix_UB_21      0.1169283000
_diffrn_orient_matrix_UB_22      -0.0482676000
_diffrn_orient_matrix_UB_23      0.0460680000
_diffrn_orient_matrix_UB_31      -0.1510799000
_diffrn_orient_matrix_UB_32      -0.0038382000
_diffrn_orient_matrix_UB_33      0.0797575000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            51948
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.746
_diffrn_reflns_theta_max         74.696
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4549
_reflns_number_gt                4406
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     0.936
_reflns_Friedel_fraction_full    0.986
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences. Completness statistics refer to single and composite 
 reflections containing twin component 1 only.
;

_computing_data_collection       
;
 CrysAlisPro system (CCD 43.112a 64-bit (release 01-03-2024))
;
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'


_refine_special_details          
;
 Refined as a 2-component inversion twin. The BASF parameter was refined to 
 41.8%.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0562P)²+0.3275P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4549
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.035
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_1 N 0.40586(6) 0.2927(2) 0.38206(11) 0.0209(3) Uani 1 1 d . . . . .
C1_1 C 0.48543(8) 0.4698(3) 0.41680(13) 0.0224(4) Uani 1 1 d . . . . .
H1_1 H 0.501900 0.588005 0.437481 0.027 Uiso 1 1 calc R U . . .
B1_1 B 0.43595(9) 0.1223(3) 0.35445(14) 0.0216(4) Uani 1 1 d . . . . .
N2_1 N 0.43071(7) 0.4649(2) 0.41172(11) 0.0229(3) Uani 1 1 d . . . . .
C2_1 C 0.52403(8) 0.3145(3) 0.39436(12) 0.0217(4) Uani 1 1 d . . . . .
C3_1 C 0.58287(9) 0.3382(3) 0.40415(14) 0.0266(4) Uani 1 1 d . . . . .
H3_1 H 0.597798 0.457237 0.426902 0.032 Uiso 1 1 calc R U . . .
C4_1 C 0.61883(8) 0.1889(3) 0.38076(14) 0.0290(4) Uani 1 1 d . . . . .
H4_1 H 0.658622 0.205332 0.386984 0.035 Uiso 1 1 calc R U . . .
C5_1 C 0.59701(8) 0.0130(3) 0.34784(14) 0.0273(4) Uani 1 1 d . . . . .
H5_1 H 0.621989 -0.089690 0.331655 0.033 Uiso 1 1 calc R U . . .
C6_1 C 0.53902(8) -0.0115(3) 0.33882(13) 0.0240(4) Uani 1 1 d . . . . .
H6_1 H 0.524630 -0.131865 0.316722 0.029 Uiso 1 1 calc R U . . .
C7_1 C 0.50096(8) 0.1385(3) 0.36181(13) 0.0206(4) Uani 1 1 d . . . . .
C8_1 C 0.40525(8) -0.0664(3) 0.32025(14) 0.0266(4) Uani 1 1 d . . . . .
H8A_1 H 0.425992 -0.121989 0.266790 0.040 Uiso 1 1 calc R U . . .
H8B_1 H 0.366539 -0.034635 0.300572 0.040 Uiso 1 1 calc R U . . .
H8C_1 H 0.404019 -0.160562 0.371990 0.040 Uiso 1 1 calc R U . . .
C1_2 C 0.34502(8) 0.3127(3) 0.37934(13) 0.0217(4) Uani 1 1 d . . . . .
C2_2 C 0.31072(8) 0.1804(3) 0.42560(14) 0.0260(4) Uani 1 1 d . . . . .
H2_2 H 0.327217 0.076255 0.459790 0.031 Uiso 1 1 calc R U . . .
C3_2 C 0.25213(9) 0.2001(3) 0.42202(16) 0.0287(4) Uani 1 1 d . . . . .
H3_2 H 0.228627 0.108702 0.453379 0.034 Uiso 1 1 calc R U . . .
C4_2 C 0.22794(8) 0.3528(3) 0.37274(14) 0.0267(4) Uani 1 1 d . . . . .
H4_2 H 0.187897 0.365746 0.369985 0.032 Uiso 1 1 calc R U . . .
C5_2 C 0.26240(8) 0.4865(3) 0.32752(15) 0.0262(4) Uani 1 1 d . . . . .
H5_2 H 0.245873 0.591660 0.294126 0.031 Uiso 1 1 calc R U . . .
C6_2 C 0.32092(8) 0.4675(3) 0.33077(14) 0.0234(4) Uani 1 1 d . . . . .
H6_2 H 0.344413 0.559730 0.300000 0.028 Uiso 1 1 calc R U . . .
N1_3 N 0.37788(6) 0.8039(2) 0.61721(10) 0.0199(3) Uani 1 1 d . . . . .
C1_3 C 0.45485(8) 0.9956(3) 0.58405(13) 0.0215(4) Uani 1 1 d . . . . .
H1_3 H 0.469575 1.117612 0.564894 0.026 Uiso 1 1 calc R U . . .
B1_3 B 0.41056(9) 0.6382(3) 0.64349(14) 0.0210(4) Uani 1 1 d . . . . .
N2_3 N 0.40035(6) 0.9819(2) 0.59059(11) 0.0214(3) Uani 1 1 d . . . . .
C2_3 C 0.49552(8) 0.8448(3) 0.60283(12) 0.0214(4) Uani 1 1 d . . . . .
C3_3 C 0.55376(8) 0.8769(3) 0.58851(14) 0.0255(4) Uani 1 1 d . . . . .
H3_3 H 0.566717 0.998661 0.565808 0.031 Uiso 1 1 calc R U . . .
C4_3 C 0.59198(8) 0.7307(3) 0.60762(14) 0.0299(4) Uani 1 1 d . . . . .
H4_3 H 0.631328 0.751232 0.597639 0.036 Uiso 1 1 calc R U . . .
C5_3 C 0.57269(9) 0.5516(3) 0.64179(15) 0.0289(4) Uani 1 1 d . . . . .
H5_3 H 0.599073 0.451658 0.655692 0.035 Uiso 1 1 calc R U . . .
C6_3 C 0.51528(8) 0.5201(3) 0.65533(13) 0.0250(4) Uani 1 1 d . . . . .
H6_3 H 0.502758 0.398291 0.678630 0.030 Uiso 1 1 calc R U . . .
C7_3 C 0.47526(8) 0.6651(3) 0.63520(13) 0.0213(4) Uani 1 1 d . . . . .
C8_3 C 0.38214(8) 0.4455(3) 0.67822(15) 0.0267(4) Uani 1 1 d . . . . .
H8A_3 H 0.405564 0.386822 0.727657 0.040 Uiso 1 1 calc R U . . .
H8B_3 H 0.378662 0.355322 0.625109 0.040 Uiso 1 1 calc R U . . .
H8C_3 H 0.344420 0.474092 0.703597 0.040 Uiso 1 1 calc R U . . .
C1_4 C 0.31703(8) 0.8144(3) 0.61967(12) 0.0208(4) Uani 1 1 d . . . . .
C2_4 C 0.28442(8) 0.6754(3) 0.57408(14) 0.0244(4) Uani 1 1 d . . . . .
H2_4 H 0.302146 0.572165 0.540966 0.029 Uiso 1 1 calc R U . . .
C3_4 C 0.22566(8) 0.6884(3) 0.57723(14) 0.0268(4) Uani 1 1 d . . . . .
H3_4 H 0.203233 0.592719 0.546742 0.032 Uiso 1 1 calc R U . . .
C4_4 C 0.19962(8) 0.8395(3) 0.62438(15) 0.0259(4) Uani 1 1 d . . . . .
H4_4 H 0.159447 0.847462 0.626059 0.031 Uiso 1 1 calc R U . . .
C5_4 C 0.23221(8) 0.9799(3) 0.66941(14) 0.0251(4) Uani 1 1 d . . . . .
H5_4 H 0.214366 1.083888 0.701789 0.030 Uiso 1 1 calc R U . . .
C6_4 C 0.29101(8) 0.9674(3) 0.66680(14) 0.0225(4) Uani 1 1 d . . . . .
H6_4 H 0.313419 1.063225 0.697192 0.027 Uiso 1 1 calc R U . . .


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_1 N2_1 1.390(2) . ?
N1_1 B1_1 1.428(3) . ?
N1_1 C1_2 1.443(2) . ?
C1_1 N2_1 1.294(2) . ?
C1_1 C2_1 1.441(3) . ?
C1_1 H1_1 0.9500 . ?
B1_1 C7_1 1.542(3) . ?
B1_1 C8_1 1.567(3) . ?
C2_1 C3_1 1.405(3) . ?
C2_1 C7_1 1.408(3) . ?
C3_1 C4_1 1.375(3) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.398(3) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.385(3) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.409(3) . ?
C6_1 H6_1 0.9500 . ?
C8_1 H8A_1 0.9800 . ?
C8_1 H8B_1 0.9800 . ?
C8_1 H8C_1 0.9800 . ?
C1_2 C2_2 1.385(3) . ?
C1_2 C6_2 1.392(3) . ?
C2_2 C3_2 1.390(3) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.387(3) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.387(3) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.388(3) . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
N1_3 N2_3 1.390(2) . ?
N1_3 B1_3 1.429(3) . ?
N1_3 C1_4 1.438(2) . ?
C1_3 N2_3 1.293(2) . ?
C1_3 C2_3 1.440(3) . ?
C1_3 H1_3 0.9500 . ?
B1_3 C7_3 1.542(3) . ?
B1_3 C8_3 1.568(3) . ?
C2_3 C7_3 1.406(3) . ?
C2_3 C3_3 1.407(3) . ?
C3_3 C4_3 1.380(3) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.403(3) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.386(3) . ?
C5_3 H5_3 0.9500 . ?
C6_3 C7_3 1.405(3) . ?
C6_3 H6_3 0.9500 . ?
C8_3 H8A_3 0.9800 . ?
C8_3 H8B_3 0.9800 . ?
C8_3 H8C_3 0.9800 . ?
C1_4 C2_4 1.389(3) . ?
C1_4 C6_4 1.392(3) . ?
C2_4 C3_4 1.391(3) . ?
C2_4 H2_4 0.9500 . ?
C3_4 C4_4 1.382(3) . ?
C3_4 H3_4 0.9500 . ?
C4_4 C5_4 1.392(3) . ?
C4_4 H4_4 0.9500 . ?
C5_4 C6_4 1.391(2) . ?
C5_4 H5_4 0.9500 . ?
C6_4 H6_4 0.9500 . ?

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
N2_1 N1_1 B1_1 125.21(15) . . ?
N2_1 N1_1 C1_2 110.26(13) . . ?
B1_1 N1_1 C1_2 124.48(15) . . ?
N2_1 C1_1 C2_1 126.82(17) . . ?
N2_1 C1_1 H1_1 116.6 . . ?
C2_1 C1_1 H1_1 116.6 . . ?
N1_1 B1_1 C7_1 114.61(16) . . ?
N1_1 B1_1 C8_1 122.60(17) . . ?
C7_1 B1_1 C8_1 122.78(17) . . ?
C1_1 N2_1 N1_1 117.39(15) . . ?
C3_1 C2_1 C7_1 120.97(17) . . ?
C3_1 C2_1 C1_1 121.09(17) . . ?
C7_1 C2_1 C1_1 117.94(17) . . ?
C4_1 C3_1 C2_1 119.94(18) . . ?
C4_1 C3_1 H3_1 120.0 . . ?
C2_1 C3_1 H3_1 120.0 . . ?
C3_1 C4_1 C5_1 120.21(18) . . ?
C3_1 C4_1 H4_1 119.9 . . ?
C5_1 C4_1 H4_1 119.9 . . ?
C6_1 C5_1 C4_1 120.06(18) . . ?
C6_1 C5_1 H5_1 120.0 . . ?
C4_1 C5_1 H5_1 120.0 . . ?
C5_1 C6_1 C7_1 121.24(17) . . ?
C5_1 C6_1 H6_1 119.4 . . ?
C7_1 C6_1 H6_1 119.4 . . ?
C2_1 C7_1 C6_1 117.58(17) . . ?
C2_1 C7_1 B1_1 118.00(16) . . ?
C6_1 C7_1 B1_1 124.43(16) . . ?
B1_1 C8_1 H8A_1 109.5 . . ?
B1_1 C8_1 H8B_1 109.5 . . ?
H8A_1 C8_1 H8B_1 109.5 . . ?
B1_1 C8_1 H8C_1 109.5 . . ?
H8A_1 C8_1 H8C_1 109.5 . . ?
H8B_1 C8_1 H8C_1 109.5 . . ?
C2_2 C1_2 C6_2 120.04(17) . . ?
C2_2 C1_2 N1_1 120.41(16) . . ?
C6_2 C1_2 N1_1 119.55(16) . . ?
C1_2 C2_2 C3_2 119.99(17) . . ?
C1_2 C2_2 H2_2 120.0 . . ?
C3_2 C2_2 H2_2 120.0 . . ?
C4_2 C3_2 C2_2 120.13(18) . . ?
C4_2 C3_2 H3_2 119.9 . . ?
C2_2 C3_2 H3_2 119.9 . . ?
C5_2 C4_2 C3_2 119.76(18) . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C4_2 C5_2 C6_2 120.36(18) . . ?
C4_2 C5_2 H5_2 119.8 . . ?
C6_2 C5_2 H5_2 119.8 . . ?
C5_2 C6_2 C1_2 119.70(17) . . ?
C5_2 C6_2 H6_2 120.1 . . ?
C1_2 C6_2 H6_2 120.1 . . ?
N2_3 N1_3 B1_3 124.88(15) . . ?
N2_3 N1_3 C1_4 110.08(14) . . ?
B1_3 N1_3 C1_4 124.95(15) . . ?
N2_3 C1_3 C2_3 126.63(17) . . ?
N2_3 C1_3 H1_3 116.7 . . ?
C2_3 C1_3 H1_3 116.7 . . ?
N1_3 B1_3 C7_3 114.73(17) . . ?
N1_3 B1_3 C8_3 121.95(17) . . ?
C7_3 B1_3 C8_3 123.32(16) . . ?
C1_3 N2_3 N1_3 117.63(14) . . ?
C7_3 C2_3 C3_3 121.21(17) . . ?
C7_3 C2_3 C1_3 118.09(17) . . ?
C3_3 C2_3 C1_3 120.70(17) . . ?
C4_3 C3_3 C2_3 119.67(18) . . ?
C4_3 C3_3 H3_3 120.2 . . ?
C2_3 C3_3 H3_3 120.2 . . ?
C3_3 C4_3 C5_3 119.96(18) . . ?
C3_3 C4_3 H4_3 120.0 . . ?
C5_3 C4_3 H4_3 120.0 . . ?
C6_3 C5_3 C4_3 120.24(18) . . ?
C6_3 C5_3 H5_3 119.9 . . ?
C4_3 C5_3 H5_3 119.9 . . ?
C5_3 C6_3 C7_3 121.15(18) . . ?
C5_3 C6_3 H6_3 119.4 . . ?
C7_3 C6_3 H6_3 119.4 . . ?
C6_3 C7_3 C2_3 117.74(18) . . ?
C6_3 C7_3 B1_3 124.35(17) . . ?
C2_3 C7_3 B1_3 117.88(16) . . ?
B1_3 C8_3 H8A_3 109.5 . . ?
B1_3 C8_3 H8B_3 109.5 . . ?
H8A_3 C8_3 H8B_3 109.5 . . ?
B1_3 C8_3 H8C_3 109.5 . . ?
H8A_3 C8_3 H8C_3 109.5 . . ?
H8B_3 C8_3 H8C_3 109.5 . . ?
C2_4 C1_4 C6_4 120.16(17) . . ?
C2_4 C1_4 N1_3 120.49(16) . . ?
C6_4 C1_4 N1_3 119.34(16) . . ?
C1_4 C2_4 C3_4 119.55(17) . . ?
C1_4 C2_4 H2_4 120.2 . . ?
C3_4 C2_4 H2_4 120.2 . . ?
C4_4 C3_4 C2_4 120.50(18) . . ?
C4_4 C3_4 H3_4 119.7 . . ?
C2_4 C3_4 H3_4 119.7 . . ?
C3_4 C4_4 C5_4 120.06(17) . . ?
C3_4 C4_4 H4_4 120.0 . . ?
C5_4 C4_4 H4_4 120.0 . . ?
C6_4 C5_4 C4_4 119.72(17) . . ?
C6_4 C5_4 H5_4 120.1 . . ?
C4_4 C5_4 H5_4 120.1 . . ?
C5_4 C6_4 C1_4 120.00(17) . . ?
C5_4 C6_4 H6_4 120.0 . . ?
C1_4 C6_4 H6_4 120.0 . . ?

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
N2_1 N1_1 B1_1 C7_1 1.4(2) . . . . ?
C1_2 N1_1 B1_1 C7_1 178.74(16) . . . . ?
N2_1 N1_1 B1_1 C8_1 -179.07(16) . . . . ?
C1_2 N1_1 B1_1 C8_1 -1.7(3) . . . . ?
C2_1 C1_1 N2_1 N1_1 0.3(3) . . . . ?
B1_1 N1_1 N2_1 C1_1 -1.7(3) . . . . ?
C1_2 N1_1 N2_1 C1_1 -179.34(16) . . . . ?
N2_1 C1_1 C2_1 C3_1 -179.17(18) . . . . ?
N2_1 C1_1 C2_1 C7_1 1.2(3) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.8(3) . . . . ?
C1_1 C2_1 C3_1 C4_1 -178.91(18) . . . . ?
C2_1 C3_1 C4_1 C5_1 -0.4(3) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.1(3) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.3(3) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.5(3) . . . . ?
C1_1 C2_1 C7_1 C6_1 179.16(16) . . . . ?
C3_1 C2_1 C7_1 B1_1 179.02(16) . . . . ?
C1_1 C2_1 C7_1 B1_1 -1.3(2) . . . . ?
C5_1 C6_1 C7_1 C2_1 0.0(3) . . . . ?
C5_1 C6_1 C7_1 B1_1 -179.53(17) . . . . ?
N1_1 B1_1 C7_1 C2_1 0.2(2) . . . . ?
C8_1 B1_1 C7_1 C2_1 -179.36(17) . . . . ?
N1_1 B1_1 C7_1 C6_1 179.65(18) . . . . ?
C8_1 B1_1 C7_1 C6_1 0.1(3) . . . . ?
N2_1 N1_1 C1_2 C2_2 -127.41(18) . . . . ?
B1_1 N1_1 C1_2 C2_2 54.9(3) . . . . ?
N2_1 N1_1 C1_2 C6_2 51.8(2) . . . . ?
B1_1 N1_1 C1_2 C6_2 -125.9(2) . . . . ?
C6_2 C1_2 C2_2 C3_2 1.3(3) . . . . ?
N1_1 C1_2 C2_2 C3_2 -179.54(17) . . . . ?
C1_2 C2_2 C3_2 C4_2 -0.5(3) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.4(3) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.4(3) . . . . ?
C4_2 C5_2 C6_2 C1_2 0.3(3) . . . . ?
C2_2 C1_2 C6_2 C5_2 -1.2(3) . . . . ?
N1_1 C1_2 C6_2 C5_2 179.60(16) . . . . ?
N2_3 N1_3 B1_3 C7_3 -3.3(2) . . . . ?
C1_4 N1_3 B1_3 C7_3 -179.52(15) . . . . ?
N2_3 N1_3 B1_3 C8_3 176.48(17) . . . . ?
C1_4 N1_3 B1_3 C8_3 0.3(3) . . . . ?
C2_3 C1_3 N2_3 N1_3 -0.9(3) . . . . ?
B1_3 N1_3 N2_3 C1_3 4.0(3) . . . . ?
C1_4 N1_3 N2_3 C1_3 -179.26(15) . . . . ?
N2_3 C1_3 C2_3 C7_3 -2.7(3) . . . . ?
N2_3 C1_3 C2_3 C3_3 176.95(17) . . . . ?
C7_3 C2_3 C3_3 C4_3 -0.8(3) . . . . ?
C1_3 C2_3 C3_3 C4_3 179.55(18) . . . . ?
C2_3 C3_3 C4_3 C5_3 -0.5(3) . . . . ?
C3_3 C4_3 C5_3 C6_3 0.8(3) . . . . ?
C4_3 C5_3 C6_3 C7_3 0.1(3) . . . . ?
C5_3 C6_3 C7_3 C2_3 -1.4(3) . . . . ?
C5_3 C6_3 C7_3 B1_3 176.75(17) . . . . ?
C3_3 C2_3 C7_3 C6_3 1.7(3) . . . . ?
C1_3 C2_3 C7_3 C6_3 -178.64(17) . . . . ?
C3_3 C2_3 C7_3 B1_3 -176.51(16) . . . . ?
C1_3 C2_3 C7_3 B1_3 3.1(2) . . . . ?
N1_3 B1_3 C7_3 C6_3 -178.54(18) . . . . ?
C8_3 B1_3 C7_3 C6_3 1.7(3) . . . . ?
N1_3 B1_3 C7_3 C2_3 -0.4(2) . . . . ?
C8_3 B1_3 C7_3 C2_3 179.80(18) . . . . ?
N2_3 N1_3 C1_4 C2_4 130.09(18) . . . . ?
B1_3 N1_3 C1_4 C2_4 -53.2(3) . . . . ?
N2_3 N1_3 C1_4 C6_4 -48.7(2) . . . . ?
B1_3 N1_3 C1_4 C6_4 128.0(2) . . . . ?
C6_4 C1_4 C2_4 C3_4 -1.1(3) . . . . ?
N1_3 C1_4 C2_4 C3_4 -179.90(16) . . . . ?
C1_4 C2_4 C3_4 C4_4 0.7(3) . . . . ?
C2_4 C3_4 C4_4 C5_4 -0.2(3) . . . . ?
C3_4 C4_4 C5_4 C6_4 -0.1(3) . . . . ?
C4_4 C5_4 C6_4 C1_4 -0.3(3) . . . . ?
C2_4 C1_4 C6_4 C5_4 0.9(3) . . . . ?
N1_3 C1_4 C6_4 C5_4 179.70(16) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-OH
_database_code_depnum_ccdc_archive 'CCDC 2394200'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.4c (K.Radacki, 2005-23)'
_audit_creation_date             2023-05-08
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C13 H11 B N2 O'
_chemical_formula_sum            'C13 H11 B N2 O'
_chemical_formula_weight         222.05
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'


_cell_length_a                   12.47340(10)
_cell_length_b                   10.92420(10)
_cell_length_c                   15.97630(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.0720(10)
_cell_angle_gamma                90
_cell_volume                     2176.96(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27100
_cell_measurement_theta_min      3.5440
_cell_measurement_theta_max      73.5560

_exptl_crystal_description       block
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 2 0.0927
1 0 -1 0.0540
0 0 -1 0.0493
0 0 1 0.0821
-2 1 2 0.1661
1 0 2 0.0716
2 -1 -1 0.1190
-1 0 -1 0.0644
-1 2 1 0.2319
1 -2 -1 0.1876
2 0 1 0.0632
-1 0 0 0.0539
1 0 0 0.0552

_shelx_estimated_absorpt_T_min   0.700
_shelx_estimated_absorpt_T_max   0.928
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     38.00 109.00   0.50    0.05    --   58.61  15.00-180.00  142
  2  ω     46.00 133.00   0.50    0.05    --   82.31  15.00-180.00  174
  3  ω     38.00 109.00   0.50    0.05    --   58.61  15.00 -90.00  142
  4  ω     46.00 133.00   0.50    0.05    --   82.31  15.00 -90.00  174
  5  ω     38.00 109.00   0.50    0.05    --   58.61  15.00 -30.00  142
  6  ω     46.00 133.00   0.50    0.05    --   82.31  15.00-150.00  174
  7  ω     46.00 133.00   0.50    0.05    --   82.31  15.00   0.00  174
  8  ω     38.00 109.00   0.50    0.05    --   58.61  15.00  60.00  142
  9  ω     46.00 133.00   0.50    0.05    --   82.31  15.00 120.00  174
 10  ω     46.00 101.00   0.50    0.05    --   82.31  15.00  90.00  110
 11  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00  60.00  100
 12  ω     34.00  93.00   0.50    0.05    --   82.31-112.00 120.00  118
 13  ω     34.00  93.00   0.50    0.05    --   82.31-112.00  30.00  118
 14  ω     16.00  66.00   0.50    0.05    --   58.61 -95.00   0.00  100
 15  ω     34.00  93.00   0.50    0.05    --   82.31-112.00 -30.00  118
 16  ω     40.00  90.00   0.50    0.05    --   82.31 -95.00 -30.00  100
 17  ω     34.00  93.00   0.50    0.05    --   82.31-112.00 -60.00  118
 18  ω     34.00  93.00   0.50    0.05    --   82.31-112.00-120.00  118
 19  ω     29.00  79.00   0.50    0.05    --   71.30 -95.00-150.00  100
 20  ω    -93.00 -28.00   0.50    0.05    --  -76.37 112.00-150.00  130
 21  ω    -88.00 -14.00   0.50    0.05    --  -60.19 126.00-180.00  148
 22  ω    -93.00 -28.00   0.50    0.05    --  -76.37 112.00 -60.00  130
 23  ω    -88.00 -14.00   0.50    0.05    --  -60.19 126.00 -90.00  148
 24  ω    -98.00 -22.00   0.50    0.05    --  -69.72 126.00   0.00  152
 25  ω    -93.00 -28.00   0.50    0.05    --  -76.37 112.00   0.00  130
 26  ω    -93.00 -28.00   0.50    0.05    --  -76.37 112.00  60.00  130
 27  ω    -93.00 -28.00   0.50    0.05    --  -76.37 112.00  90.00  130
 28  ω    -98.00 -22.00   0.50    0.05    --  -69.72 126.00 120.00  152
 29  ω    -93.00 -28.00   0.50    0.05    --  -76.37 112.00 150.00  130
 30  ω    -93.00 -28.00   0.50    0.05    --  -76.37 112.00 120.00  130
 31  ω    -93.00 -28.00   0.50    0.05    --  -76.37 112.00 -90.00  130
 32  ω   -127.00 -40.00   0.50    0.05    --  -76.37 -15.00  60.00  174
 33  ω   -127.00 -40.00   0.50    0.05    --  -76.37 -15.00 150.00  174
 34  ω   -127.00 -40.00   0.50    0.05    --  -76.37 -15.00   0.00  174
 35  ω   -127.00 -40.00   0.50    0.05    --  -76.37 -15.00 -90.00  174
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0265820000
_diffrn_orient_matrix_UB_12      0.1358945000
_diffrn_orient_matrix_UB_13      0.0155233000
_diffrn_orient_matrix_UB_21      0.0612369000
_diffrn_orient_matrix_UB_22      0.0047406000
_diffrn_orient_matrix_UB_23      -0.0836294000
_diffrn_orient_matrix_UB_31      -0.1038548000
_diffrn_orient_matrix_UB_32      0.0376053000
_diffrn_orient_matrix_UB_33      -0.0454196000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            43469
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.543
_diffrn_reflns_theta_max         73.680
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4336
_reflns_number_gt                3975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0605P)²+0.6859P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4336
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.046
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 0.27289(7) 0.34913(8) 0.28149(6) 0.0171(2) Uani 1 1 d . . . . .
O1 O 0.08216(6) 0.32868(7) 0.29872(5) 0.02305(19) Uani 1 1 d . . . . .
H30 H 0.0197(11) 0.3546(12) 0.2768(7) 0.035 Uiso 1 1 calc R U . . .
C1 C 0.35014(8) 0.49409(10) 0.19485(7) 0.0204(2) Uani 1 1 d . . . . .
H1 H 0.413420 0.533445 0.175651 0.024 Uiso 1 1 calc R U . . .
B1 B 0.16455(10) 0.38306(11) 0.25804(8) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.36253(7) 0.40719(8) 0.24898(6) 0.0190(2) Uani 1 1 d . . . . .
O2 O 0.57854(6) 0.41699(8) 0.28964(5) 0.0246(2) Uani 1 1 d . . . . .
H2 H 0.5181(11) 0.3875(12) 0.2658(8) 0.037 Uiso 1 1 calc R U . . .
C2 C 0.24976(8) 0.53738(10) 0.16061(7) 0.0192(2) Uani 1 1 d . . . . .
B2 B 0.66470(10) 0.36343(11) 0.25426(8) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.15051(10) 0.66593(11) 0.06566(8) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.148672 0.728100 0.024103 0.031 Uiso 1 1 calc R U . . .
C7 C 0.24706(9) 0.63057(10) 0.10013(7) 0.0230(2) Uani 1 1 d . . . . .
H7 H 0.311643 0.669190 0.082977 0.028 Uiso 1 1 calc R U . . .
C5 C 0.05526(10) 0.61033(11) 0.09184(8) 0.0276(3) Uani 1 1 d . . . . .
H5 H -0.011051 0.634104 0.067462 0.033 Uiso 1 1 calc R U . . .
C4 C 0.05725(9) 0.52070(11) 0.15320(7) 0.0238(3) Uani 1 1 d . . . . .
H4 H -0.008085 0.484947 0.171470 0.029 Uiso 1 1 calc R U . . .
N4 N 0.86343(7) 0.34426(9) 0.25453(6) 0.0197(2) Uani 1 1 d . . . . .
C3 C 0.15455(8) 0.48201(10) 0.18875(7) 0.0186(2) Uani 1 1 d . . . . .
C10 C 0.26775(9) 0.05840(10) 0.40309(7) 0.0232(2) Uani 1 1 d . . . . .
H10 H 0.223968 -0.012314 0.408455 0.028 Uiso 1 1 calc R U . . .
C9 C 0.23779(8) 0.15087(10) 0.34836(7) 0.0199(2) Uani 1 1 d . . . . .
H9 H 0.174279 0.142776 0.315946 0.024 Uiso 1 1 calc R U . . .
C8 C 0.30105(8) 0.25605(10) 0.34088(7) 0.0178(2) Uani 1 1 d . . . . .
C13 C 0.39296(8) 0.26746(10) 0.39001(7) 0.0205(2) Uani 1 1 d . . . . .
H13 H 0.435078 0.339770 0.386950 0.025 Uiso 1 1 calc R U . . .
C12 C 0.42295(9) 0.17319(11) 0.44342(7) 0.0236(3) Uani 1 1 d . . . . .
H12 H 0.486588 0.180760 0.475745 0.028 Uiso 1 1 calc R U . . .
C11 C 0.36114(9) 0.06810(11) 0.45016(7) 0.0249(3) Uani 1 1 d . . . . .
H11 H 0.382367 0.003606 0.486461 0.030 Uiso 1 1 calc R U . . .
C17 C 0.56791(9) 0.21716(10) 0.14790(7) 0.0230(2) Uani 1 1 d . . . . .
H17 H 0.500264 0.249399 0.163986 0.028 Uiso 1 1 calc R U . . .
N3 N 0.77043(7) 0.40103(8) 0.28172(6) 0.0175(2) Uani 1 1 d . . . . .
C18 C 0.57272(9) 0.12675(11) 0.08707(8) 0.0260(3) Uani 1 1 d . . . . .
H18 H 0.508531 0.098152 0.061675 0.031 Uiso 1 1 calc R U . . .
C19 C 0.67161(10) 0.07722(10) 0.06278(7) 0.0242(3) Uani 1 1 d . . . . .
H19 H 0.674612 0.015984 0.020632 0.029 Uiso 1 1 calc R U . . .
C14 C 0.85686(8) 0.25688(10) 0.20002(7) 0.0209(2) Uani 1 1 d . . . . .
H14 H 0.922297 0.219381 0.183693 0.025 Uiso 1 1 calc R U . . .
C15 C 0.75998(8) 0.21048(10) 0.16140(7) 0.0190(2) Uani 1 1 d . . . . .
C20 C 0.76446(9) 0.11800(10) 0.10049(7) 0.0219(2) Uani 1 1 d . . . . .
H20 H 0.831548 0.083468 0.085233 0.026 Uiso 1 1 calc R U . . .
C16 C 0.66153(8) 0.26172(10) 0.18603(7) 0.0185(2) Uani 1 1 d . . . . .
C21 C 0.79114(8) 0.49791(10) 0.34032(7) 0.0185(2) Uani 1 1 d . . . . .
C22 C 0.72136(9) 0.59776(10) 0.34468(7) 0.0203(2) Uani 1 1 d . . . . .
H22 H 0.659530 0.600076 0.309935 0.024 Uiso 1 1 calc R U . . .
C23 C 0.74179(9) 0.69335(10) 0.39933(7) 0.0228(2) Uani 1 1 d . . . . .
H23 H 0.693386 0.760372 0.401963 0.027 Uiso 1 1 calc R U . . .
C24 C 0.83167(9) 0.69266(11) 0.45015(7) 0.0248(3) Uani 1 1 d . . . . .
H24 H 0.845500 0.758593 0.487409 0.030 Uiso 1 1 calc R U . . .
C25 C 0.90135(9) 0.59353(11) 0.44561(8) 0.0259(3) Uani 1 1 d . . . . .
H25 H 0.963642 0.592367 0.479880 0.031 Uiso 1 1 calc R U . . .
C26 C 0.88147(9) 0.49605(10) 0.39177(7) 0.0223(2) Uani 1 1 d . . . . .
H26 H 0.929296 0.428414 0.390068 0.027 Uiso 1 1 calc R U . . .


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 N2 1.3869(12) . ?
N1 C8 1.4342(14) . ?
N1 B1 1.4500(15) . ?
O1 B1 1.3538(14) . ?
C1 N2 1.2933(14) . ?
C1 C2 1.4453(15) . ?
B1 C3 1.5521(16) . ?
O2 B2 1.3484(14) . ?
C2 C7 1.4040(15) . ?
C2 C3 1.4070(15) . ?
B2 N3 1.4488(15) . ?
B2 C16 1.5570(16) . ?
C6 C7 1.3789(17) . ?
C6 C5 1.3988(17) . ?
C5 C4 1.3857(16) . ?
C4 C3 1.4044(15) . ?
N4 C14 1.2946(15) . ?
N4 N3 1.3858(12) . ?
C10 C9 1.3869(16) . ?
C10 C11 1.3898(17) . ?
C9 C8 1.3992(15) . ?
C8 C13 1.3941(15) . ?
C13 C12 1.3884(16) . ?
C12 C11 1.3872(17) . ?
C17 C18 1.3870(16) . ?
C17 C16 1.4035(15) . ?
N3 C21 1.4362(14) . ?
C18 C19 1.4021(17) . ?
C19 C20 1.3787(16) . ?
C14 C15 1.4478(15) . ?
C15 C20 1.4039(15) . ?
C15 C16 1.4062(15) . ?
C21 C26 1.3941(15) . ?
C21 C22 1.3972(15) . ?
C22 C23 1.3846(16) . ?
C23 C24 1.3834(16) . ?
C24 C25 1.3906(17) . ?
C25 C26 1.3911(16) . ?

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
N2 N1 C8 112.03(8) . . ?
N2 N1 B1 122.54(9) . . ?
C8 N1 B1 125.42(9) . . ?
N2 C1 C2 126.58(10) . . ?
O1 B1 N1 118.14(10) . . ?
O1 B1 C3 125.98(10) . . ?
N1 B1 C3 115.87(9) . . ?
C1 N2 N1 119.37(9) . . ?
C7 C2 C3 120.81(10) . . ?
C7 C2 C1 121.18(10) . . ?
C3 C2 C1 118.01(10) . . ?
O2 B2 N3 118.40(10) . . ?
O2 B2 C16 125.70(10) . . ?
N3 B2 C16 115.89(9) . . ?
C7 C6 C5 120.04(11) . . ?
C6 C7 C2 119.88(10) . . ?
C4 C5 C6 120.26(11) . . ?
C5 C4 C3 120.90(11) . . ?
C14 N4 N3 119.25(9) . . ?
C4 C3 C2 118.08(10) . . ?
C4 C3 B1 124.52(10) . . ?
C2 C3 B1 117.40(9) . . ?
C9 C10 C11 120.71(11) . . ?
C10 C9 C8 120.03(10) . . ?
C13 C8 C9 119.26(10) . . ?
C13 C8 N1 120.65(9) . . ?
C9 C8 N1 120.07(9) . . ?
C12 C13 C8 120.03(10) . . ?
C11 C12 C13 120.81(10) . . ?
C12 C11 C10 119.12(11) . . ?
C18 C17 C16 120.95(11) . . ?
N4 N3 C21 112.60(8) . . ?
N4 N3 B2 122.70(9) . . ?
C21 N3 B2 124.70(9) . . ?
C17 C18 C19 120.50(10) . . ?
C20 C19 C18 119.55(11) . . ?
N4 C14 C15 126.64(10) . . ?
C20 C15 C16 121.06(10) . . ?
C20 C15 C14 120.89(10) . . ?
C16 C15 C14 118.05(10) . . ?
C19 C20 C15 120.08(10) . . ?
C17 C16 C15 117.84(10) . . ?
C17 C16 B2 124.87(10) . . ?
C15 C16 B2 117.29(9) . . ?
C26 C21 C22 119.02(10) . . ?
C26 C21 N3 121.21(10) . . ?
C22 C21 N3 119.75(9) . . ?
C23 C22 C21 120.40(10) . . ?
C24 C23 C22 120.96(11) . . ?
C23 C24 C25 118.66(11) . . ?
C24 C25 C26 121.16(10) . . ?
C25 C26 C21 119.79(10) . . ?

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
N2 N1 B1 O1 -174.13(9) . . . . ?
C8 N1 B1 O1 4.39(16) . . . . ?
N2 N1 B1 C3 4.61(15) . . . . ?
C8 N1 B1 C3 -176.87(9) . . . . ?
C2 C1 N2 N1 -2.20(16) . . . . ?
C8 N1 N2 C1 -179.56(9) . . . . ?
B1 N1 N2 C1 -0.86(15) . . . . ?
N2 C1 C2 C7 -178.15(11) . . . . ?
N2 C1 C2 C3 0.88(17) . . . . ?
C5 C6 C7 C2 0.96(17) . . . . ?
C3 C2 C7 C6 -2.11(17) . . . . ?
C1 C2 C7 C6 176.89(10) . . . . ?
C7 C6 C5 C4 0.83(18) . . . . ?
C6 C5 C4 C3 -1.51(18) . . . . ?
C5 C4 C3 C2 0.37(17) . . . . ?
C5 C4 C3 B1 179.59(11) . . . . ?
C7 C2 C3 C4 1.43(16) . . . . ?
C1 C2 C3 C4 -177.60(10) . . . . ?
C7 C2 C3 B1 -177.84(10) . . . . ?
C1 C2 C3 B1 3.13(15) . . . . ?
O1 B1 C3 C4 -6.20(18) . . . . ?
N1 B1 C3 C4 175.17(10) . . . . ?
O1 B1 C3 C2 173.02(10) . . . . ?
N1 B1 C3 C2 -5.61(14) . . . . ?
C11 C10 C9 C8 -0.84(16) . . . . ?
C10 C9 C8 C13 -1.15(16) . . . . ?
C10 C9 C8 N1 177.07(9) . . . . ?
N2 N1 C8 C13 30.96(13) . . . . ?
B1 N1 C8 C13 -147.70(11) . . . . ?
N2 N1 C8 C9 -147.24(9) . . . . ?
B1 N1 C8 C9 34.11(15) . . . . ?
C9 C8 C13 C12 2.30(16) . . . . ?
N1 C8 C13 C12 -175.92(9) . . . . ?
C8 C13 C12 C11 -1.48(17) . . . . ?
C13 C12 C11 C10 -0.51(17) . . . . ?
C9 C10 C11 C12 1.68(17) . . . . ?
C14 N4 N3 C21 -178.48(9) . . . . ?
C14 N4 N3 B2 2.60(15) . . . . ?
O2 B2 N3 N4 174.29(9) . . . . ?
C16 B2 N3 N4 -4.97(15) . . . . ?
O2 B2 N3 C21 -4.50(16) . . . . ?
C16 B2 N3 C21 176.24(9) . . . . ?
C16 C17 C18 C19 0.46(18) . . . . ?
C17 C18 C19 C20 0.74(18) . . . . ?
N3 N4 C14 C15 1.04(17) . . . . ?
N4 C14 C15 C20 177.52(11) . . . . ?
N4 C14 C15 C16 -1.77(17) . . . . ?
C18 C19 C20 C15 -1.45(17) . . . . ?
C16 C15 C20 C19 1.00(16) . . . . ?
C14 C15 C20 C19 -178.27(10) . . . . ?
C18 C17 C16 C15 -0.90(16) . . . . ?
C18 C17 C16 B2 179.53(10) . . . . ?
C20 C15 C16 C17 0.18(16) . . . . ?
C14 C15 C16 C17 179.47(10) . . . . ?
C20 C15 C16 B2 179.78(10) . . . . ?
C14 C15 C16 B2 -0.93(15) . . . . ?
O2 B2 C16 C17 4.35(18) . . . . ?
N3 B2 C16 C17 -176.45(10) . . . . ?
O2 B2 C16 C15 -175.22(10) . . . . ?
N3 B2 C16 C15 3.98(14) . . . . ?
N4 N3 C21 C26 -28.03(13) . . . . ?
B2 N3 C21 C26 150.87(11) . . . . ?
N4 N3 C21 C22 150.27(10) . . . . ?
B2 N3 C21 C22 -30.83(15) . . . . ?
C26 C21 C22 C23 0.01(16) . . . . ?
N3 C21 C22 C23 -178.33(10) . . . . ?
C21 C22 C23 C24 0.48(17) . . . . ?
C22 C23 C24 C25 -0.23(17) . . . . ?
C23 C24 C25 C26 -0.51(18) . . . . ?
C24 C25 C26 C21 1.00(18) . . . . ?
C22 C21 C26 C25 -0.73(16) . . . . ?
N3 C21 C26 C25 177.58(10) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-TBA
_database_code_depnum_ccdc_archive 'CCDC 2394205'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.5k (K.Radacki, 2005-24)'
_audit_creation_date             2024-10-28
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C25 H20 B N2, C16 H36 N'
_chemical_formula_sum            'C41 H56 B N3'
_chemical_formula_weight         601.69
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'


_cell_length_a                   12.26330(10)
_cell_length_b                   17.39660(10)
_cell_length_c                   16.9860(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.5390(10)
_cell_angle_gamma                90
_cell_volume                     3491.33(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30113
_cell_measurement_theta_min      4.5060
_cell_measurement_theta_max      73.7260

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.222
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 2 0.1926
1 -2 2 0.2628
-2 -9 -5 0.1978
-4 0 -8 0.1526
-2 10 -4 0.2645
0 11 0 0.2843
1 -11 2 0.3408
0 0 11 0.1768
0 0 -11 0.1718
-1 -6 9 0.2068
-1 -8 -7 0.2197
0 4 10 0.1979
-3 0 11 0.1559
-4 -8 7 0.2034
-1 4 10 0.1955
3 1 -11 0.1845
3 10 -3 0.2208
5 0 -10 0.1834
-5 0 10 0.1510
-5 -8 5 0.1836
4 10 -1 0.2019
7 3 -6 0.1555
-6 -7 3 0.1344
-7 -3 6 0.1189
7 2 -6 0.1480
4 -8 -7 0.3184
7 4 -1 0.1788
8 0 -3 0.2049
-7 -4 1 0.1218
-7 4 4 0.2167

_shelx_estimated_absorpt_T_min   0.735
_shelx_estimated_absorpt_T_max   0.879
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     30.00  56.00   0.50    0.05    --   18.00  60.00 -46.08   52
  2  ω     30.00  56.00   0.50    0.05    --   18.00  60.00  -0.59   52
  3  ω     34.00  60.00   0.50    0.05    --   22.00  58.00 -92.61   52
  4  ω     34.00  60.00   0.50    0.05    --   22.00  57.00-143.75   52
  5  ω     34.00  60.00   0.50    0.05    --   22.00  58.00  45.19   52
  6  ω     30.00  60.00   0.50    0.05    --   18.00  59.00 132.41   60
  7  ω     34.00  60.00   0.50    0.05    --   22.00  57.00  93.38   52
  8  ω     46.00 133.00   0.50    0.05    --   82.26  15.00 120.00  174
  9  ω     24.00  99.00   0.50    0.05    --   71.44-126.00 150.00  150
 10  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00   0.00  100
 11  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00  90.00  100
 12  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 120.00  100
 13  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 150.00  100
 14  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 -30.00  100
 15  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 -60.00  100
 16  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00 -90.00  100
 17  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00-120.00  100
 18  ω     42.00  93.00   0.50    0.05    --   85.25 -97.00-140.49  102
 19  ω     37.00  93.00   0.50    0.05    --   82.26-112.00-180.00  112
 20  ω     40.00  90.00   0.50    0.05    --   82.26 -95.00  30.00  100
 21  ω     46.00 133.00   0.50    0.05    --   82.26  15.00 -60.00  174
 22  ω     -5.00  21.00   0.50    0.05    --  -10.00  77.00 -85.37   52
 23  ω    -97.00 -33.00   0.50    0.05    --  -79.50 115.00-134.20  128
 24  ω    -97.00 -32.00   0.50    0.05    --  -78.00 114.00 -50.19  130
 25  ω    -96.00 -34.00   0.50    0.05    --  -79.50 114.00  12.64  124
 26  ω    -97.00 -32.00   0.50    0.05    --  -78.00 114.00 139.85  130
 27  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00  60.00  122
 28  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00 -30.00  122
 29  ω    -92.00 -35.00   0.50    0.05    --  -79.50 102.00 -92.85  114
 30  ω    -92.00 -31.00   0.50    0.05    --  -76.36 112.00-180.00  122
 31  ω    -94.00 -59.00   0.50    0.05    --  -46.00 -51.00-179.47   70
 32  ω   -125.00 -90.00   0.50    0.05    --  -79.50 -62.00-135.66   70
 33  ω   -100.00 -62.00   0.50    0.05    --  -50.00 -41.00  28.10   76
 34  ω   -120.00 -86.00   0.50    0.05    --  -74.00 -59.00 -31.29   68
 35  ω   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00  41.68   68
 36  ω   -120.00 -86.00   0.50    0.05    --  -74.00 -59.00 -63.58   68
 37  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -58.00-114.30   70
 38  ω   -121.00 -86.00   0.50    0.05    --  -74.00 -58.00 -96.66   70
 39  ω   -125.00 -90.00   0.50    0.05    --  -78.00 -57.00 -11.63   70
 40  ω   -120.00 -86.00   0.50    0.05    --  -74.00 -59.00  55.91   68
 41  ω    -79.00 -44.00   0.50    0.05    --  -30.00 -49.00 120.21   70
 42  ω   -125.00 -90.00   0.50    0.05    --  -78.00 -55.00 169.35   70
 43  ω   -120.00 -86.00   0.50    0.05    --  -74.00 -60.00 133.45   68
 44  ω   -106.00 -71.00   0.50    0.05    --  -58.00 -52.00 103.63   70
 45  ω   -122.00 -87.00   0.50    0.05    --  -74.00 -53.00  96.62   70
 46  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -50.00  86.38   70
 47  ω   -110.00 -75.00   0.50    0.05    --  -62.00 -51.00 -74.41   70
 48  ω   -110.00 -75.00   0.50    0.05    --  -62.00 -52.00-136.62   70
 49  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00 -84.10   70
 50  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -50.00 -45.86   70
 51  ω   -107.00 -72.00   0.50    0.05    --  -58.00 -48.00 -33.37   70
 52  ω   -103.00 -67.00   0.50    0.05    --  -54.00 -46.00  -5.62   72
 53  ω   -129.00 -93.00   0.50    0.05    --  -79.50 -46.00   1.56   72
 54  ω   -129.00 -93.00   0.50    0.05    --  -79.50 -48.00  62.47   72
 55  ω   -115.00 -80.00   0.50    0.05    --  -66.00 -47.00 134.77   70
 56  ω   -120.00 -83.00   0.50    0.05    --  -70.00 -46.00 177.56   74
 57  ω   -130.00 -92.00   0.50    0.05    --  -79.50 -42.00 132.69   76
 58  ω   -127.00 -90.00   0.50    0.05    --  -79.50-127.00  63.45   74
 59  ω   -126.00 -92.00   0.50    0.05    --  -79.50-122.00 170.59   68
 60  ω   -126.00 -92.00   0.50    0.05    --  -79.50-123.00 108.80   68
 61  ω   -126.00 -93.00   0.50    0.05    --  -79.50-120.00 115.71   66
 62  ω   -127.00 -90.00   0.50    0.05    --  -79.50-126.00  32.38   74
 63  ω   -125.00 -94.00   0.50    0.05    --  -79.50-119.00 -13.78   62
 64  ω   -126.00 -92.00   0.50    0.05    --  -79.50-123.00 -31.36   68
 65  ω   -125.00 -94.00   0.50    0.05    --  -79.50-119.00 -75.04   62
 66  ω   -126.00 -93.00   0.50    0.05    --  -79.50-121.00-101.01   66
 67  ω   -126.00 -93.00   0.50    0.05    --  -79.50-121.00-128.53   66
 68  ω   -126.00 -93.00   0.50    0.05    --  -79.50-120.00-158.26   66
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0845216000
_diffrn_orient_matrix_UB_12      -0.0370629000
_diffrn_orient_matrix_UB_13      0.0740476000
_diffrn_orient_matrix_UB_21      -0.0907648000
_diffrn_orient_matrix_UB_22      0.0010926000
_diffrn_orient_matrix_UB_23      0.0475480000
_diffrn_orient_matrix_UB_31      -0.0401925000
_diffrn_orient_matrix_UB_32      -0.0804297000
_diffrn_orient_matrix_UB_33      -0.0334278000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            38740
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.524
_diffrn_reflns_theta_max         74.723
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3501
_reflns_number_gt                3345
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       
;
 CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))
;
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          
;
 The borat main molecule was located on a symmetry element und was refined as 
 special position disorder. The atomic displacement parameters of the 
 diazaborinine atoms and the phenyl atoms were restraint with RIGU keyword in 
 ShelXL input ('enhanced rigid bond' restraint for all bonds in the 
 connectivity list). The displacement parameters of the diazaborinine atoms 
 and the phenyl atoms were restrained to the same value with similarity 
 restraint SIMU. The Uii displacement parameters of the diazaborinine atoms 
 and the phenyl atoms were restrained with ISOR keyword to approximate 
 isotropic behavior. The distances between atoms B1_1 to C1_3 and B_1 to C1_4 
 were restrained during refinement to the same value using SADI. Idealized 
 geometry of the phenyl substituents were restraint using AFIX 66.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0474P)²+1.9229P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3501
_refine_ls_number_parameters     308
_refine_ls_number_restraints     1321
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
 
 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
 
 * -0.1343 (0.0018)  B1_1^a
 *  0.0347 (0.0018)  N1_1^a
 *  0.0558 (0.0020)  N2_1^a
 *  0.0025 (0.0020)  C1_1^a
 * -0.0094 (0.0025)  C2_1^a
 * -0.0348 (0.0024)  C3_1^a
 * -0.0510 (0.0023)  C4_1^a
 *  0.0427 (0.0022)  C5_1^a
 *  0.0847 (0.0023)  C6_1^a
 *  0.0089 (0.0022)  C7_1^a
 
 Rms deviation of fitted atoms =   0.0594
 
 Angle to previous plane (with approximate esd) = 17.990 ( 0.158 )
 
 *  0.0000 (0.0000)  C1_2^a
 *  0.0000 (0.0000)  C2_2^a
 *  0.0000 (0.0000)  C3_2^a
 *  0.0000 (0.0000)  C4_2^a
 *  0.0000 (0.0000)  C5_2^a
 *  0.0000 (0.0000)  C6_2^a
 
 Rms deviation of fitted atoms =   0.0000
 
 Angle to previous plane (with approximate esd) = 19.465 ( 0.157 )
 
 * -0.0287 (0.0019)  N1_1^a
 *  0.0366 (0.0019)  N2_1^a
 *  0.0112 (0.0021)  C1_1^a
 * -0.0100 (0.0025)  C2_1^a
 * -0.0018 (0.0022)  C3_1^a
 * -0.0264 (0.0022)  C4_1^a
 *  0.0236 (0.0022)  C5_1^a
 *  0.0315 (0.0021)  C6_1^a
 * -0.0360 (0.0021)  C7_1^a
 
 Rms deviation of fitted atoms =   0.0257
;

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
B1_1 B 0.53147(18) 0.97992(13) 0.26886(13) 0.0211(4) Uani 0.5 1 d D U P A -1
N1_1 N 0.46805(14) 1.05550(9) 0.22770(10) 0.0209(3) Uani 0.5 1 d . U P A -1
N2_1 N 0.5110(4) 1.12853(9) 0.2406(3) 0.0243(7) Uani 0.5 1 d . U P A -1
C1_1 C 0.60816(18) 1.14005(12) 0.29292(13) 0.0258(4) Uani 0.5 1 d . U P A -1
H1_1 H 0.635871 1.191301 0.297047 0.031 Uiso 0.5 1 calc R U P A -1
C2_1 C 0.6793(2) 1.08427(19) 0.34568(15) 0.0227(5) Uani 0.5 1 d . U P A -1
C3_1 C 0.7805(3) 1.1057(2) 0.4004(2) 0.0280(6) Uani 0.5 1 d . U P A -1
H3_1 H 0.802777 1.158133 0.403053 0.034 Uiso 0.5 1 calc R U P A -1
C4_1 C 0.8507(3) 1.0525(2) 0.4518(2) 0.0273(14) Uani 0.5 1 d . U P A -1
H4_1 H 0.921952 1.067104 0.486745 0.033 Uiso 0.5 1 calc R U P A -1
C5_1 C 0.8115(3) 0.9775(2) 0.4495(2) 0.0270(6) Uani 0.5 1 d . U P A -1
H5_1 H 0.855160 0.940337 0.485477 0.032 Uiso 0.5 1 calc R U P A -1
C6_1 C 0.7089(2) 0.95540(14) 0.39519(15) 0.0232(5) Uani 0.5 1 d . U P A -1
H6_1 H 0.683696 0.903820 0.395870 0.028 Uiso 0.5 1 calc R U P A -1
C7_1 C 0.6426(2) 1.00750(18) 0.34002(15) 0.0198(5) Uani 0.5 1 d . U P A -1
C1_2 C 0.36113(12) 1.05511(14) 0.16812(9) 0.0200(4) Uani 0.5 1 d G U P A -1
C2_2 C 0.31833(18) 0.98564(11) 0.13248(13) 0.0218(5) Uani 0.5 1 d G U P A -1
H2_2 H 0.360210 0.939580 0.147913 0.026 Uiso 0.5 1 calc R U P A -1
C3_2 C 0.2143(2) 0.98358(12) 0.07425(16) 0.0265(8) Uani 0.5 1 d G U P A -1
H3_2 H 0.185006 0.936100 0.049891 0.032 Uiso 0.5 1 calc R U P A -1
C4_2 C 0.1530(2) 1.05097(16) 0.0517(2) 0.0299(15) Uani 0.5 1 d G U P A -1
H4_2 H 0.081851 1.049559 0.011872 0.036 Uiso 0.5 1 calc R U P A -1
C5_2 C 0.1958(2) 1.12044(12) 0.08731(19) 0.0265(8) Uani 0.5 1 d G U P A -1
H5_2 H 0.153898 1.166499 0.071875 0.032 Uiso 0.5 1 calc R U P A -1
C6_2 C 0.29985(18) 1.12250(11) 0.14554(12) 0.0245(5) Uani 0.5 1 d G U P A -1
H6_2 H 0.329102 1.169981 0.169898 0.029 Uiso 0.5 1 calc R U P A -1
C1_3 C 0.4484(4) 0.9311(3) 0.3107(3) 0.0232(8) Uani 0.5 1 d D U P A -1
C2_3 C 0.4212(5) 0.9558(3) 0.3835(3) 0.0228(9) Uani 0.5 1 d . U P A -1
H2_3 H 0.447469 1.004949 0.404515 0.027 Uiso 0.5 1 calc R U P A -1
C3_3 C 0.3592(5) 0.9134(3) 0.4258(3) 0.0225(9) Uani 0.5 1 d . U P A -1
H3_3 H 0.344161 0.933904 0.473637 0.027 Uiso 0.5 1 calc R U P A -1
C4_3 C 0.3194(6) 0.8408(3) 0.3977(3) 0.0244(9) Uani 0.5 1 d . U P A -1
H4_3 H 0.277174 0.810914 0.425969 0.029 Uiso 0.5 1 calc R U P A -1
C5_3 C 0.3428(5) 0.8133(3) 0.3274(4) 0.0259(9) Uani 0.5 1 d . U P A -1
H5_3 H 0.316930 0.763765 0.307244 0.031 Uiso 0.5 1 calc R U P A -1
C6_3 C 0.4036(5) 0.8577(3) 0.2863(3) 0.0245(9) Uani 0.5 1 d . U P A -1
H6_3 H 0.416097 0.836909 0.237728 0.029 Uiso 0.5 1 calc R U P A -1
C1_4 C 0.5779(4) 0.9297(3) 0.2004(2) 0.0230(9) Uani 0.5 1 d DG U P A -1
C2_4 C 0.5830(4) 0.9656(2) 0.1284(3) 0.0235(10) Uani 0.5 1 d G U P A -1
H2_4 H 0.553481 1.016072 0.116377 0.028 Uiso 0.5 1 calc R U P A -1
C3_4 C 0.6312(5) 0.9278(3) 0.0740(3) 0.0240(10) Uani 0.5 1 d G U P A -1
H3_4 H 0.634668 0.952317 0.024724 0.029 Uiso 0.5 1 calc R U P A -1
C4_4 C 0.6744(5) 0.8540(3) 0.0915(3) 0.0244(10) Uani 0.5 1 d G U P A -1
H4_4 H 0.707313 0.828110 0.054338 0.029 Uiso 0.5 1 calc R U P A -1
C5_4 C 0.6693(5) 0.8181(2) 0.1636(3) 0.0241(11) Uani 0.5 1 d G U P A -1
H5_4 H 0.698772 0.767656 0.175605 0.029 Uiso 0.5 1 calc R U P A -1
C6_4 C 0.6211(4) 0.8560(3) 0.2180(2) 0.0241(10) Uani 0.5 1 d G U P A -1
H6_4 H 0.617586 0.831410 0.267259 0.029 Uiso 0.5 1 calc R U P A -1
N1_7 N 0.500000 0.55613(7) 0.750000 0.0209(3) Uani 1 2 d S T P . .
C1_5 C 0.42445(8) 0.50666(6) 0.68337(6) 0.0236(2) Uani 1 1 d . . . . .
H1A_5 H 0.472749 0.478983 0.654442 0.028 Uiso 1 1 calc R U . . .
H1B_5 H 0.373547 0.540854 0.643247 0.028 Uiso 1 1 calc R U . . .
C2_5 C 0.35244(9) 0.44799(6) 0.71343(7) 0.0292(2) Uani 1 1 d . . . . .
H2A_5 H 0.294877 0.475136 0.734244 0.035 Uiso 1 1 calc R U . . .
H2B_5 H 0.401100 0.418037 0.759036 0.035 Uiso 1 1 calc R U . . .
C3_5 C 0.29348(10) 0.39333(6) 0.64471(7) 0.0318(3) Uani 1 1 d . . . . .
H3A_5 H 0.231869 0.366339 0.661003 0.038 Uiso 1 1 calc R U . . .
H3B_5 H 0.258561 0.423951 0.595252 0.038 Uiso 1 1 calc R U . . .
C4_5 C 0.37198(12) 0.33374(7) 0.62340(9) 0.0441(3) Uani 1 1 d . . . . .
H4A_5 H 0.328374 0.300007 0.580111 0.066 Uiso 1 1 calc R U . . .
H4B_5 H 0.407007 0.303039 0.671970 0.066 Uiso 1 1 calc R U . . .
H4C_5 H 0.431085 0.359819 0.604417 0.066 Uiso 1 1 calc R U . . .
C1_6 C 0.57494(8) 0.60569(6) 0.71225(6) 0.0232(2) Uani 1 1 d . . . . .
H1A_6 H 0.631509 0.631745 0.756906 0.028 Uiso 1 1 calc R U . . .
H1B_6 H 0.616754 0.571533 0.683901 0.028 Uiso 1 1 calc R U . . .
C2_6 C 0.51412(9) 0.66625(6) 0.65215(6) 0.0262(2) Uani 1 1 d . . . . .
H2A_6 H 0.468781 0.699400 0.678735 0.031 Uiso 1 1 calc R U . . .
H2B_6 H 0.461690 0.640846 0.604725 0.031 Uiso 1 1 calc R U . . .
C3_6 C 0.59783(10) 0.71549(7) 0.62276(8) 0.0328(3) Uani 1 1 d . . . . .
H3A_6 H 0.646447 0.743626 0.669880 0.039 Uiso 1 1 calc R U . . .
H3B_6 H 0.647217 0.681620 0.600465 0.039 Uiso 1 1 calc R U . . .
C4_6 C 0.54034(10) 0.77266(7) 0.55787(7) 0.0320(3) Uani 1 1 d . . . . .
H4A_6 H 0.597767 0.802224 0.540408 0.048 Uiso 1 1 calc R U . . .
H4B_6 H 0.493614 0.807679 0.580237 0.048 Uiso 1 1 calc R U . . .
H4C_6 H 0.492354 0.745149 0.510896 0.048 Uiso 1 1 calc R U . . .


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
B1_1 N1_1 1.591(3) . ?
B1_1 C1_3 1.629(4) . ?
B1_1 C7_1 1.633(3) . ?
B1_1 C1_4 1.671(4) . ?
N1_1 N2_1 1.370(3) . ?
N1_1 C1_2 1.426(2) . ?
N2_1 C1_1 1.297(5) . ?
C1_1 C2_1 1.444(3) . ?
C1_1 H1_1 0.9500 . ?
C2_1 C3_1 1.388(5) . ?
C2_1 C7_1 1.404(4) . ?
C3_1 C4_1 1.399(4) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.388(4) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.400(4) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.397(4) . ?
C6_1 H6_1 0.9500 . ?
C1_2 C2_2 1.3900 . ?
C1_2 C6_2 1.3900 . ?
C2_2 C3_2 1.3900 . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.3900 . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.3900 . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3900 . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
C1_3 C6_3 1.409(4) . ?
C1_3 C2_3 1.430(4) . ?
C2_3 C3_3 1.388(5) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.391(5) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.386(5) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.385(5) . ?
C5_3 H5_3 0.9500 . ?
C6_3 H6_3 0.9500 . ?
C1_4 C2_4 1.3900 . ?
C1_4 C6_4 1.3900 . ?
C2_4 C3_4 1.3900 . ?
C2_4 H2_4 0.9500 . ?
C3_4 C4_4 1.3900 . ?
C3_4 H3_4 0.9500 . ?
C4_4 C5_4 1.3900 . ?
C4_4 H4_4 0.9500 . ?
C5_4 C6_4 1.3900 . ?
C5_4 H5_4 0.9500 . ?
C6_4 H6_4 0.9500 . ?
N1_7 C1_6 1.5215(11) . ?
N1_7 C1_6 1.5215(11) 2_656 ?
N1_7 C1_5 1.5225(12) 2_656 ?
N1_7 C1_5 1.5226(12) . ?
C1_5 C2_5 1.5243(14) . ?
C1_5 H1A_5 0.9900 . ?
C1_5 H1B_5 0.9900 . ?
C2_5 C3_5 1.5288(15) . ?
C2_5 H2A_5 0.9900 . ?
C2_5 H2B_5 0.9900 . ?
C3_5 C4_5 1.5229(17) . ?
C3_5 H3A_5 0.9900 . ?
C3_5 H3B_5 0.9900 . ?
C4_5 H4A_5 0.9800 . ?
C4_5 H4B_5 0.9800 . ?
C4_5 H4C_5 0.9800 . ?
C1_6 C2_6 1.5167(14) . ?
C1_6 H1A_6 0.9900 . ?
C1_6 H1B_6 0.9900 . ?
C2_6 C3_6 1.5204(15) . ?
C2_6 H2A_6 0.9900 . ?
C2_6 H2B_6 0.9900 . ?
C3_6 C4_6 1.5116(15) . ?
C3_6 H3A_6 0.9900 . ?
C3_6 H3B_6 0.9900 . ?
C4_6 H4A_6 0.9800 . ?
C4_6 H4B_6 0.9800 . ?
C4_6 H4C_6 0.9800 . ?

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
N1_1 B1_1 C1_3 109.5(2) . . ?
N1_1 B1_1 C7_1 107.18(18) . . ?
C1_3 B1_1 C7_1 109.0(2) . . ?
N1_1 B1_1 C1_4 110.1(2) . . ?
C1_3 B1_1 C1_4 113.63(17) . . ?
C7_1 B1_1 C1_4 107.2(2) . . ?
N2_1 N1_1 C1_2 111.0(2) . . ?
N2_1 N1_1 B1_1 125.1(2) . . ?
C1_2 N1_1 B1_1 123.80(16) . . ?
C1_1 N2_1 N1_1 119.7(3) . . ?
N2_1 C1_1 C2_1 127.8(2) . . ?
N2_1 C1_1 H1_1 116.1 . . ?
C2_1 C1_1 H1_1 116.1 . . ?
C3_1 C2_1 C7_1 120.9(2) . . ?
C3_1 C2_1 C1_1 121.2(3) . . ?
C7_1 C2_1 C1_1 117.9(3) . . ?
C2_1 C3_1 C4_1 122.1(3) . . ?
C2_1 C3_1 H3_1 119.0 . . ?
C4_1 C3_1 H3_1 119.0 . . ?
C5_1 C4_1 C3_1 117.0(3) . . ?
C5_1 C4_1 H4_1 121.5 . . ?
C3_1 C4_1 H4_1 121.5 . . ?
C4_1 C5_1 C6_1 121.3(3) . . ?
C4_1 C5_1 H5_1 119.3 . . ?
C6_1 C5_1 H5_1 119.3 . . ?
C7_1 C6_1 C5_1 121.5(2) . . ?
C7_1 C6_1 H6_1 119.3 . . ?
C5_1 C6_1 H6_1 119.3 . . ?
C6_1 C7_1 C2_1 117.0(2) . . ?
C6_1 C7_1 B1_1 121.7(3) . . ?
C2_1 C7_1 B1_1 121.2(2) . . ?
C2_2 C1_2 C6_2 120.0 . . ?
C2_2 C1_2 N1_1 118.79(18) . . ?
C6_2 C1_2 N1_1 121.21(18) . . ?
C3_2 C2_2 C1_2 120.0 . . ?
C3_2 C2_2 H2_2 120.0 . . ?
C1_2 C2_2 H2_2 120.0 . . ?
C4_2 C3_2 C2_2 120.0 . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 120.0 . . ?
C3_2 C4_2 H4_2 120.0 . . ?
C5_2 C4_2 H4_2 120.0 . . ?
C4_2 C5_2 C6_2 120.0 . . ?
C4_2 C5_2 H5_2 120.0 . . ?
C6_2 C5_2 H5_2 120.0 . . ?
C5_2 C6_2 C1_2 120.0 . . ?
C5_2 C6_2 H6_2 120.0 . . ?
C1_2 C6_2 H6_2 120.0 . . ?
C6_3 C1_3 C2_3 111.3(3) . . ?
C6_3 C1_3 B1_1 125.8(4) . . ?
C2_3 C1_3 B1_1 122.6(4) . . ?
C3_3 C2_3 C1_3 125.1(3) . . ?
C3_3 C2_3 H2_3 117.4 . . ?
C1_3 C2_3 H2_3 117.4 . . ?
C2_3 C3_3 C4_3 119.6(3) . . ?
C2_3 C3_3 H3_3 120.2 . . ?
C4_3 C3_3 H3_3 120.2 . . ?
C5_3 C4_3 C3_3 118.3(3) . . ?
C5_3 C4_3 H4_3 120.9 . . ?
C3_3 C4_3 H4_3 120.9 . . ?
C6_3 C5_3 C4_3 120.4(3) . . ?
C6_3 C5_3 H5_3 119.8 . . ?
C4_3 C5_3 H5_3 119.8 . . ?
C5_3 C6_3 C1_3 125.3(3) . . ?
C5_3 C6_3 H6_3 117.4 . . ?
C1_3 C6_3 H6_3 117.4 . . ?
C2_4 C1_4 C6_4 120.0 . . ?
C2_4 C1_4 B1_1 118.8(3) . . ?
C6_4 C1_4 B1_1 120.9(3) . . ?
C1_4 C2_4 C3_4 120.0 . . ?
C1_4 C2_4 H2_4 120.0 . . ?
C3_4 C2_4 H2_4 120.0 . . ?
C4_4 C3_4 C2_4 120.0 . . ?
C4_4 C3_4 H3_4 120.0 . . ?
C2_4 C3_4 H3_4 120.0 . . ?
C3_4 C4_4 C5_4 120.0 . . ?
C3_4 C4_4 H4_4 120.0 . . ?
C5_4 C4_4 H4_4 120.0 . . ?
C6_4 C5_4 C4_4 120.0 . . ?
C6_4 C5_4 H5_4 120.0 . . ?
C4_4 C5_4 H5_4 120.0 . . ?
C5_4 C6_4 C1_4 120.0 . . ?
C5_4 C6_4 H6_4 120.0 . . ?
C1_4 C6_4 H6_4 120.0 . . ?
C1_6 N1_7 C1_6 110.97(10) . 2_656 ?
C1_6 N1_7 C1_5 108.51(5) . 2_656 ?
C1_6 N1_7 C1_5 108.85(5) 2_656 2_656 ?
C1_6 N1_7 C1_5 108.85(5) . . ?
C1_6 N1_7 C1_5 108.52(5) 2_656 . ?
C1_5 N1_7 C1_5 111.16(11) 2_656 . ?
N1_7 C1_5 C2_5 114.92(8) . . ?
N1_7 C1_5 H1A_5 108.5 . . ?
C2_5 C1_5 H1A_5 108.5 . . ?
N1_7 C1_5 H1B_5 108.5 . . ?
C2_5 C1_5 H1B_5 108.5 . . ?
H1A_5 C1_5 H1B_5 107.5 . . ?
C1_5 C2_5 C3_5 111.02(9) . . ?
C1_5 C2_5 H2A_5 109.4 . . ?
C3_5 C2_5 H2A_5 109.4 . . ?
C1_5 C2_5 H2B_5 109.4 . . ?
C3_5 C2_5 H2B_5 109.4 . . ?
H2A_5 C2_5 H2B_5 108.0 . . ?
C4_5 C3_5 C2_5 113.90(10) . . ?
C4_5 C3_5 H3A_5 108.8 . . ?
C2_5 C3_5 H3A_5 108.8 . . ?
C4_5 C3_5 H3B_5 108.8 . . ?
C2_5 C3_5 H3B_5 108.8 . . ?
H3A_5 C3_5 H3B_5 107.7 . . ?
C3_5 C4_5 H4A_5 109.5 . . ?
C3_5 C4_5 H4B_5 109.5 . . ?
H4A_5 C4_5 H4B_5 109.5 . . ?
C3_5 C4_5 H4C_5 109.5 . . ?
H4A_5 C4_5 H4C_5 109.5 . . ?
H4B_5 C4_5 H4C_5 109.5 . . ?
C2_6 C1_6 N1_7 115.69(8) . . ?
C2_6 C1_6 H1A_6 108.4 . . ?
N1_7 C1_6 H1A_6 108.4 . . ?
C2_6 C1_6 H1B_6 108.4 . . ?
N1_7 C1_6 H1B_6 108.4 . . ?
H1A_6 C1_6 H1B_6 107.4 . . ?
C1_6 C2_6 C3_6 111.02(9) . . ?
C1_6 C2_6 H2A_6 109.4 . . ?
C3_6 C2_6 H2A_6 109.4 . . ?
C1_6 C2_6 H2B_6 109.4 . . ?
C3_6 C2_6 H2B_6 109.4 . . ?
H2A_6 C2_6 H2B_6 108.0 . . ?
C4_6 C3_6 C2_6 112.71(9) . . ?
C4_6 C3_6 H3A_6 109.0 . . ?
C2_6 C3_6 H3A_6 109.0 . . ?
C4_6 C3_6 H3B_6 109.0 . . ?
C2_6 C3_6 H3B_6 109.0 . . ?
H3A_6 C3_6 H3B_6 107.8 . . ?
C3_6 C4_6 H4A_6 109.5 . . ?
C3_6 C4_6 H4B_6 109.5 . . ?
H4A_6 C4_6 H4B_6 109.5 . . ?
C3_6 C4_6 H4C_6 109.5 . . ?
H4A_6 C4_6 H4C_6 109.5 . . ?
H4B_6 C4_6 H4C_6 109.5 . . ?

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
C1_3 B1_1 N1_1 N2_1 128.5(3) . . . . ?
C7_1 B1_1 N1_1 N2_1 10.4(3) . . . . ?
C1_4 B1_1 N1_1 N2_1 -105.9(3) . . . . ?
C1_3 B1_1 N1_1 C1_2 -55.6(3) . . . . ?
C7_1 B1_1 N1_1 C1_2 -173.76(16) . . . . ?
C1_4 B1_1 N1_1 C1_2 70.0(3) . . . . ?
C1_2 N1_1 N2_1 C1_1 -179.9(2) . . . . ?
B1_1 N1_1 N2_1 C1_1 -3.6(3) . . . . ?
N1_1 N2_1 C1_1 C2_1 -3.6(4) . . . . ?
N2_1 C1_1 C2_1 C3_1 -178.3(3) . . . . ?
N2_1 C1_1 C2_1 C7_1 1.5(4) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.4(4) . . . . ?
C1_1 C2_1 C3_1 C4_1 -179.8(2) . . . . ?
C2_1 C3_1 C4_1 C5_1 -3.9(4) . . . . ?
C3_1 C4_1 C5_1 C6_1 3.1(4) . . . . ?
C4_1 C5_1 C6_1 C7_1 1.2(4) . . . . ?
C5_1 C6_1 C7_1 C2_1 -4.7(4) . . . . ?
C5_1 C6_1 C7_1 B1_1 172.1(2) . . . . ?
C3_1 C2_1 C7_1 C6_1 3.9(4) . . . . ?
C1_1 C2_1 C7_1 C6_1 -176.0(2) . . . . ?
C3_1 C2_1 C7_1 B1_1 -172.9(3) . . . . ?
C1_1 C2_1 C7_1 B1_1 7.3(3) . . . . ?
N1_1 B1_1 C7_1 C6_1 171.5(2) . . . . ?
C1_3 B1_1 C7_1 C6_1 53.1(3) . . . . ?
C1_4 B1_1 C7_1 C6_1 -70.4(3) . . . . ?
N1_1 B1_1 C7_1 C2_1 -11.9(3) . . . . ?
C1_3 B1_1 C7_1 C2_1 -130.3(3) . . . . ?
C1_4 B1_1 C7_1 C2_1 106.3(3) . . . . ?
N2_1 N1_1 C1_2 C2_2 164.16(16) . . . . ?
B1_1 N1_1 C1_2 C2_2 -12.2(2) . . . . ?
N2_1 N1_1 C1_2 C6_2 -15.9(2) . . . . ?
B1_1 N1_1 C1_2 C6_2 167.78(16) . . . . ?
C6_2 C1_2 C2_2 C3_2 0.0 . . . . ?
N1_1 C1_2 C2_2 C3_2 180.0(2) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.0 . . . . ?
C2_2 C3_2 C4_2 C5_2 0.0 . . . . ?
C3_2 C4_2 C5_2 C6_2 0.0 . . . . ?
C4_2 C5_2 C6_2 C1_2 0.0 . . . . ?
C2_2 C1_2 C6_2 C5_2 0.0 . . . . ?
N1_1 C1_2 C6_2 C5_2 -180.0(2) . . . . ?
N1_1 B1_1 C1_3 C6_3 114.6(4) . . . . ?
C7_1 B1_1 C1_3 C6_3 -128.4(4) . . . . ?
C1_4 B1_1 C1_3 C6_3 -8.9(5) . . . . ?
N1_1 B1_1 C1_3 C2_3 -71.8(4) . . . . ?
C7_1 B1_1 C1_3 C2_3 45.2(5) . . . . ?
C1_4 B1_1 C1_3 C2_3 164.7(4) . . . . ?
C6_3 C1_3 C2_3 C3_3 0.4(5) . . . . ?
B1_1 C1_3 C2_3 C3_3 -174.0(4) . . . . ?
C1_3 C2_3 C3_3 C4_3 0.4(5) . . . . ?
C2_3 C3_3 C4_3 C5_3 -0.3(4) . . . . ?
C3_3 C4_3 C5_3 C6_3 -0.5(4) . . . . ?
C4_3 C5_3 C6_3 C1_3 1.4(5) . . . . ?
C2_3 C1_3 C6_3 C5_3 -1.3(5) . . . . ?
B1_1 C1_3 C6_3 C5_3 172.9(5) . . . . ?
N1_1 B1_1 C1_4 C2_4 15.8(3) . . . . ?
C1_3 B1_1 C1_4 C2_4 139.0(3) . . . . ?
C7_1 B1_1 C1_4 C2_4 -100.4(3) . . . . ?
N1_1 B1_1 C1_4 C6_4 -170.3(3) . . . . ?
C1_3 B1_1 C1_4 C6_4 -47.1(5) . . . . ?
C7_1 B1_1 C1_4 C6_4 73.4(3) . . . . ?
C6_4 C1_4 C2_4 C3_4 0.0 . . . . ?
B1_1 C1_4 C2_4 C3_4 173.9(4) . . . . ?
C1_4 C2_4 C3_4 C4_4 0.0 . . . . ?
C2_4 C3_4 C4_4 C5_4 0.0 . . . . ?
C3_4 C4_4 C5_4 C6_4 0.0 . . . . ?
C4_4 C5_4 C6_4 C1_4 0.0 . . . . ?
C2_4 C1_4 C6_4 C5_4 0.0 . . . . ?
B1_1 C1_4 C6_4 C5_4 -173.8(4) . . . . ?
C1_6 N1_7 C1_5 C2_5 174.25(8) . . . . ?
C1_6 N1_7 C1_5 C2_5 -64.88(11) 2_656 . . . ?
C1_5 N1_7 C1_5 C2_5 54.78(7) 2_656 . . . ?
N1_7 C1_5 C2_5 C3_5 -171.44(9) . . . . ?
C1_5 C2_5 C3_5 C4_5 74.45(13) . . . . ?
C1_6 N1_7 C1_6 C2_6 -52.80(7) 2_656 . . . ?
C1_5 N1_7 C1_6 C2_6 -172.35(8) 2_656 . . . ?
C1_5 N1_7 C1_6 C2_6 66.55(11) . . . . ?
N1_7 C1_6 C2_6 C3_6 176.28(9) . . . . ?
C1_6 C2_6 C3_6 C4_6 175.62(9) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-NCO
_database_code_depnum_ccdc_archive 'CCDC 2394208'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.5d (K.Radacki, 2005-23)'
_audit_creation_date             2024-08-08
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C20 H14 B N3 O, C16 H36 N'
_chemical_formula_sum            'C36 H50 B N4 O'
_chemical_formula_weight         565.61
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'


_cell_length_a                   17.0832(2)
_cell_length_b                   10.34500(10)
_cell_length_c                   18.6658(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.8040(10)
_cell_angle_gamma                90
_cell_volume                     3297.09(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    44829
_cell_measurement_theta_min      2.6260
_cell_measurement_theta_max      73.4970

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 6 -1 0.1381
-6 -6 -2 0.1383
10 -3 3 0.1530
9 3 3 0.1825
0 7 1 0.1641
6 6 2 0.1868
-1 2 -12 0.0664
1 -2 11 0.0378
-5 6 0 0.1342
1 0 -12 0.0835
4 -5 8 0.1134
2 4 -10 0.1001
-2 -3 10 0.0775
-7 1 10 0.1582

_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.945
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     36.00  99.00   0.50    0.05    --   78.63-123.00-129.00  126
  2  ω     40.00 101.00   0.50    0.05    --   82.25-125.00-122.48  122
  3  ω     29.00  93.00   0.50    0.05    --   71.40-123.00-129.00  128
  4  ω     71.00  97.00   0.50    0.05    --   82.25-114.00 -93.84   52
  5  ω     18.00  80.00   0.50    0.05    --   58.63-123.00-129.00  124
  6  ω     37.00  92.00   0.50    0.05    --   78.63-112.00-120.00  110
  7  ω     37.00  92.00   0.50    0.05    --   78.63-112.00 -30.00  110
  8  ω     37.00  92.00   0.50    0.05    --   78.63-112.00   0.00  110
  9  ω     44.00  93.00   0.50    0.05    --   82.25-106.00  15.94   98
 10  ω     38.00  70.00   0.50    0.05    --   78.63-112.00 120.00   64
 11  ω     43.00  98.00   0.50    0.05    --   82.25-116.00 158.94  110
 12  ω     55.00  98.00   0.50    0.05    --   82.25-116.00  44.08   86
 13  ω     42.00  90.00   0.50    0.05    --   82.25-102.00-108.74   96
 14  ω     38.00 106.00   0.50    0.05    --   58.63  15.00 -90.00  136
 15  ω     45.00 126.00   0.50    0.05    --   78.63  15.00-150.00  162
 16  ω     45.00 126.00   0.50    0.05    --   78.63  15.00-150.00  162
 17  ω     46.00  98.00   0.50    0.05    --   78.63  15.00 -60.00  104
 18  ω     45.00 126.00   0.50    0.05    --   78.63  15.00  60.00  162
 19  ω     45.00 126.00   0.50    0.05    --   78.63  15.00  60.00  162
 20  ω     45.00 126.00   0.50    0.05    --   78.63  15.00 150.00  162
 21  ω     27.00  56.00   0.50    0.05    --   10.00  46.00 161.07   58
 22  ω     55.00  84.00   0.50    0.05    --   38.00  50.00   0.55   58
 23  ω     55.00  83.00   0.50    0.05    --   38.00  51.00 -38.65   56
 24  ω     20.00  46.00   0.50    0.05    --    6.00  63.00 107.65   52
 25  ω    -99.00 -35.00   0.50    0.05    --  -78.50 124.00 124.96  128
 26  ω    -91.00 -27.00   0.50    0.05    --  -69.75 123.00 -49.00  128
 27  ω    -96.00 -32.00   0.50    0.05    --  -75.18 123.00 -49.00  128
 28  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00 -43.47  128
 29  ω    -82.00 -17.00   0.50    0.05    --  -60.27 123.00 -49.00  130
 30  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00-115.22  128
 31  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00-139.50  128
 32  ω    -99.00 -35.00   0.50    0.05    --  -78.50 122.00 -83.09  128
 33  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00   1.39  128
 34  ω    -97.00 -36.00   0.50    0.05    --  -78.50 118.00  24.03  122
 35  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00 110.79  128
 36  ω    -85.00 -38.00   0.50    0.05    --  -78.50 100.00 112.55   94
 37  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00  30.00  112
 38  ω    -97.00 -35.00   0.50    0.05    --  -78.50 120.00  60.31  124
 39  ω    -96.00 -36.00   0.50    0.05    --  -78.50 116.00-105.45  120
 40  ω   -122.00 -43.00   0.50    0.05    --  -75.18 -15.00-120.00  158
 41  ω   -103.00 -75.00   0.50    0.05    --  -58.00 -51.00 -94.58   56
 42  ω   -121.00 -93.00   0.50    0.05    --  -78.50 -61.00 -11.77   56
 43  ω   -118.00 -90.00   0.50    0.05    --  -74.00 -54.00  41.64   56
 44  ω   -103.00 -75.00   0.50    0.05    --  -58.00 -51.00 128.10   56
 45  ω    -95.00 -67.00   0.50    0.05    --  -50.00 -50.00  91.10   56
 46  ω   -124.00 -96.00   0.50    0.05    --  -78.50 -49.00  35.18   56
 47  ω   -116.00 -86.00   0.50    0.05    --  -70.00 -45.00 149.82   60
 48  ω    -92.00 -63.00   0.50    0.05    --  -46.00 -47.00  35.88   58
 49  ω   -113.00 -82.00   0.50    0.05    --  -66.00 -44.00  78.05   62
 50  ω   -124.00 -96.00   0.50    0.05    --  -78.50 -48.00   9.33   56
 51  ω   -125.00 -94.00   0.50    0.05    --  -78.50 -42.00 175.28   62
 52  ω   -124.00 -95.00   0.50    0.05    --  -78.50 -50.00-111.39   58
 53  ω   -121.00 -90.00   0.50    0.05    --  -74.00 -43.00-139.97   62
 54  ω   -121.00 -90.00   0.50    0.05    --  -74.00 -43.00-172.24   62
 55  ω    -99.00 -71.00   0.50    0.05    --  -54.00 -50.00-136.12   56
 56  ω   -121.00 -89.00   0.50    0.05    --  -74.00 -41.00 -63.42   64
 57  ω   -126.00 -94.00   0.50    0.05    --  -78.50 -41.00 138.91   64
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0797730000
_diffrn_orient_matrix_UB_12      0.0693956000
_diffrn_orient_matrix_UB_13      -0.0010053000
_diffrn_orient_matrix_UB_21      -0.0000810000
_diffrn_orient_matrix_UB_22      0.0131211000
_diffrn_orient_matrix_UB_23      0.0822241000
_diffrn_orient_matrix_UB_31      0.0420943000
_diffrn_orient_matrix_UB_32      -0.1311055000
_diffrn_orient_matrix_UB_33      0.0078308000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            12050
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         73.899
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.534
_diffrn_reflns_point_group_measured_fraction_full 0.548
_reflns_number_total             12050
_reflns_number_gt                11545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.095
_reflns_Friedel_fraction_max     0.093
_reflns_Friedel_fraction_full    0.097
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique Friedel pairs 
 measured divided by the number that would be possible theoretically, 
 ignoring centric projections and systematic absences. Completness statistics 
 refer to single and composite reflections containing twin component 1 only.
;

_computing_data_collection       
;
 CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))
;
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_twin_special_details            
;
 Component 2 rotated by 179.9972° 
 around [-0.03 0.00 1.00] (reciprocal) or [0.00 -0.00 1.00] (direct)
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5199 40703 35484 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4801 40624 35484 nmt -1.0001 0.0002 -0.0580 0.0000 -0.9999 0.0001 0.0004
-0.0001 0.9999

_twin_formation_mechanism        gt
_twin_dimensionality             triperiodic
_twin_morphology                 polysynthetic

_refine_special_details          
;
 Refined as a 4-component twin. The BASF parameters were refined to 2.7, 1.8 
 and 44.6%. Refined as 2-component twin with additionally inversion twinning. 
 The third scale factor with basf = 43.96% belongs to the inverted second 
 component. HKLF5 file for 4-component twin was generated using HKLF5Tools 
 (S. I. Ivlev, M. Conrad, F. Kraus, 2019). The atomic displacement parameters 
 of the atoms of the disordered n-butyl group C9_10 to C12_101 were restraint 
 with RIGU keyword with esd = 0.008 in ShelXL input ('enhanced rigid bond' 
 restraint for all bonds in the connectivity list). The displacement 
 parameters of the atoms of the disordered n-butyl group C9_10 to C12_101 
 were restrained to the same value with similarity restraint SIMU with esd = 
 0.008. The Uii displacement parameters of the atoms of the disordered 
 n-butyl group C9_10 to C12_101 were restrained with ISOR keyword with esd = 
 0.008 to approximate isotropic behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0707P)²+0.5372P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         12050
_refine_ls_number_parameters     804
_refine_ls_number_restraints     176
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
B1_1 B 0.7559(2) 0.8637(3) 0.43575(19) 0.0326(7) Uani 1 1 d . . . . .
C2_1 C 0.81835(18) 1.0710(3) 0.37906(17) 0.0352(6) Uani 1 1 d . . . . .
N1_1 N 0.68826(15) 0.9610(2) 0.45028(14) 0.0328(5) Uani 1 1 d . . . . .
C1_1 C 0.7480(2) 1.1386(3) 0.4017(2) 0.0439(8) Uani 1 1 d . . . . .
N3_1 N 0.68984(17) 1.0898(2) 0.43448(16) 0.0394(6) Uani 1 1 d . . . . .
C3_1 C 0.8767(2) 1.1361(4) 0.3438(2) 0.0470(8) Uani 1 1 d . . . . .
H3_1 H 0.870659 1.225493 0.333206 0.056 Uiso 1 1 calc R U . . .
C4_1 C 0.9428(2) 1.0728(4) 0.3240(2) 0.0500(9) Uani 1 1 d . . . . .
H4_1 H 0.982002 1.117329 0.298816 0.060 Uiso 1 1 calc R U . . .
C5_1 C 0.95223(19) 0.9433(4) 0.3411(2) 0.0458(8) Uani 1 1 d . . . . .
H5_1 H 0.998883 0.899625 0.328900 0.055 Uiso 1 1 calc R U . . .
C6_1 C 0.89386(19) 0.8770(3) 0.37586(19) 0.0402(7) Uani 1 1 d . . . . .
H6_1 H 0.900614 0.787759 0.386277 0.048 Uiso 1 1 calc R U . . .
C7_1 C 0.82460(17) 0.9400(3) 0.39603(16) 0.0323(6) Uani 1 1 d . . . . .
C1_2 C 0.61786(17) 0.9250(3) 0.48289(17) 0.0337(6) Uani 1 1 d . . . . .
C2_2 C 0.60703(18) 0.7993(3) 0.50692(17) 0.0351(6) Uani 1 1 d . . . . .
H2_2 H 0.647718 0.737779 0.501657 0.042 Uiso 1 1 calc R U . . .
C3_2 C 0.5380(2) 0.7616(3) 0.53852(18) 0.0408(7) Uani 1 1 d . . . . .
H3_2 H 0.532203 0.675120 0.554681 0.049 Uiso 1 1 calc R U . . .
C4_2 C 0.47693(19) 0.8503(4) 0.54664(18) 0.0419(7) Uani 1 1 d . . . . .
H4_2 H 0.429597 0.825388 0.568209 0.050 Uiso 1 1 calc R U . . .
C5_2 C 0.4876(2) 0.9750(3) 0.5223(2) 0.0441(8) Uani 1 1 d . . . . .
H5_2 H 0.446724 1.036277 0.527209 0.053 Uiso 1 1 calc R U . . .
C6_2 C 0.5562(2) 1.0128(3) 0.49116(18) 0.0389(7) Uani 1 1 d . . . . .
H6_2 H 0.561639 1.099412 0.475104 0.047 Uiso 1 1 calc R U . . .
C1_3 C 0.72531(17) 0.7414(3) 0.38760(17) 0.0327(6) Uani 1 1 d . . . . .
C2_3 C 0.7645(2) 0.6223(3) 0.38703(19) 0.0386(7) Uani 1 1 d . . . . .
H2_3 H 0.808215 0.608983 0.418897 0.046 Uiso 1 1 calc R U . . .
C3_3 C 0.7408(2) 0.5231(3) 0.3409(2) 0.0457(8) Uani 1 1 d . . . . .
H3_3 H 0.768788 0.443679 0.341632 0.055 Uiso 1 1 calc R U . . .
C4_3 C 0.6780(2) 0.5382(4) 0.2946(2) 0.0516(9) Uani 1 1 d . . . . .
H4_3 H 0.662359 0.470051 0.263128 0.062 Uiso 1 1 calc R U . . .
C5_3 C 0.6371(2) 0.6549(3) 0.2939(2) 0.0448(8) Uani 1 1 d . . . . .
H5_3 H 0.592852 0.666374 0.262470 0.054 Uiso 1 1 calc R U . . .
C6_3 C 0.66127(18) 0.7538(3) 0.33941(17) 0.0340(6) Uani 1 1 d . . . . .
H6_3 H 0.633328 0.833236 0.337853 0.041 Uiso 1 1 calc R U . . .
O1_4 O 0.85206(19) 0.6768(3) 0.59515(18) 0.0664(8) Uani 1 1 d . . . . .
N1_4 N 0.79033(16) 0.8134(3) 0.50954(15) 0.0383(6) Uani 1 1 d . . . . .
C2_4 C 0.82125(19) 0.7448(3) 0.55088(19) 0.0414(7) Uani 1 1 d . . . . .
N1_5 N 0.82668(15) 0.2088(3) 0.63578(15) 0.0361(6) Uani 1 1 d . . . . .
C1_5 C 0.87757(19) 0.2875(3) 0.68948(17) 0.0382(7) Uani 1 1 d . . . . .
H1A_5 H 0.842614 0.338935 0.719746 0.046 Uiso 1 1 calc R U . . .
H1B_5 H 0.906761 0.226595 0.721317 0.046 Uiso 1 1 calc R U . . .
C2_5 C 0.9361(2) 0.3788(3) 0.65575(19) 0.0442(8) Uani 1 1 d . . . . .
H2A_5 H 0.907649 0.439237 0.623072 0.053 Uiso 1 1 calc R U . . .
H2B_5 H 0.972830 0.327998 0.626972 0.053 Uiso 1 1 calc R U . . .
C3_5 C 0.9824(2) 0.4561(4) 0.7126(2) 0.0469(8) Uani 1 1 d . . . . .
H3A_5 H 1.007653 0.394799 0.746877 0.056 Uiso 1 1 calc R U . . .
H3B_5 H 1.024554 0.503992 0.688848 0.056 Uiso 1 1 calc R U . . .
C4_5 C 0.9341(2) 0.5510(4) 0.7539(2) 0.0516(9) Uani 1 1 d . . . . .
H4A_5 H 0.968474 0.600066 0.786976 0.077 Uiso 1 1 calc R U . . .
H4B_5 H 0.895171 0.503899 0.781160 0.077 Uiso 1 1 calc R U . . .
H4C_5 H 0.907449 0.610490 0.720402 0.077 Uiso 1 1 calc R U . . .
C5_5 C 0.87749(18) 0.1220(3) 0.59113(18) 0.0383(7) Uani 1 1 d . . . . .
H5A_5 H 0.843673 0.080437 0.553734 0.046 Uiso 1 1 calc R U . . .
H5B_5 H 0.915653 0.176901 0.566403 0.046 Uiso 1 1 calc R U . . .
C6_5 C 0.92220(19) 0.0172(3) 0.6313(2) 0.0424(7) Uani 1 1 d . . . . .
H6A_5 H 0.885639 -0.052097 0.645093 0.051 Uiso 1 1 calc R U . . .
H6B_5 H 0.946657 0.053598 0.675641 0.051 Uiso 1 1 calc R U . . .
C7_5 C 0.9854(2) -0.0393(4) 0.5847(2) 0.0507(9) Uani 1 1 d . . . . .
H7A_5 H 0.961201 -0.067507 0.538395 0.061 Uiso 1 1 calc R U . . .
H7B_5 H 1.024198 0.028861 0.574501 0.061 Uiso 1 1 calc R U . . .
C8_5 C 1.0272(2) -0.1530(4) 0.6198(3) 0.0580(10) Uani 1 1 d . . . . .
H8A_5 H 1.070223 -0.180878 0.589886 0.087 Uiso 1 1 calc R U . . .
H8B_5 H 0.990219 -0.224534 0.625121 0.087 Uiso 1 1 calc R U . . .
H8C_5 H 1.048252 -0.127270 0.667125 0.087 Uiso 1 1 calc R U . . .
C9_5 C 0.7701(2) 0.1296(3) 0.67950(19) 0.0400(7) Uani 1 1 d . . . . .
H9A_5 H 0.800702 0.067122 0.709204 0.048 Uiso 1 1 calc R U . . .
H9B_5 H 0.743138 0.188458 0.712501 0.048 Uiso 1 1 calc R U . . .
C10_5 C 0.7083(2) 0.0554(4) 0.6356(2) 0.0457(8) Uani 1 1 d . . . . .
H10A_5 H 0.733989 0.003269 0.598546 0.055 Uiso 1 1 calc R U . . .
H10B_5 H 0.672137 0.116990 0.611097 0.055 Uiso 1 1 calc R U . . .
C11_5 C 0.6616(3) -0.0346(4) 0.6850(3) 0.0637(12) Uani 1 1 d . . . . .
H11A_5 H 0.650871 0.012141 0.729909 0.076 Uiso 1 1 calc R U . . .
H11B_5 H 0.610646 -0.055300 0.661037 0.076 Uiso 1 1 calc R U . . .
C12_5 C 0.7029(3) -0.1577(5) 0.7033(3) 0.0677(12) Uani 1 1 d . . . . .
H12A_5 H 0.669332 -0.211619 0.732652 0.102 Uiso 1 1 calc R U . . .
H12B_5 H 0.751744 -0.138461 0.730190 0.102 Uiso 1 1 calc R U . . .
H12C_5 H 0.714858 -0.203878 0.659144 0.102 Uiso 1 1 calc R U . . .
C13_5 C 0.7823(2) 0.2985(3) 0.58403(18) 0.0409(7) Uani 1 1 d . . . . .
H13A_5 H 0.820987 0.345188 0.555334 0.049 Uiso 1 1 calc R U . . .
H13B_5 H 0.750219 0.244633 0.550497 0.049 Uiso 1 1 calc R U . . .
C14_5 C 0.7296(2) 0.3963(3) 0.6171(2) 0.0454(8) Uani 1 1 d . . . . .
H14A_5 H 0.760070 0.447611 0.653003 0.054 Uiso 1 1 calc R U . . .
H14B_5 H 0.687376 0.351065 0.642169 0.054 Uiso 1 1 calc R U . . .
C15_5 C 0.6932(2) 0.4873(4) 0.5605(2) 0.0482(8) Uani 1 1 d . . . . .
H15A_5 H 0.665674 0.557653 0.585404 0.058 Uiso 1 1 calc R U . . .
H15B_5 H 0.735948 0.527236 0.533560 0.058 Uiso 1 1 calc R U . . .
C16_5 C 0.6363(2) 0.4245(4) 0.5077(2) 0.0492(8) Uani 1 1 d . . . . .
H16A_5 H 0.615416 0.489844 0.474231 0.074 Uiso 1 1 calc R U . . .
H16B_5 H 0.593207 0.385521 0.533550 0.074 Uiso 1 1 calc R U . . .
H16C_5 H 0.663399 0.357307 0.480952 0.074 Uiso 1 1 calc R U . . .
N1_6 N 0.19734(17) 1.4479(3) 0.55401(15) 0.0384(6) Uani 1 1 d . . . . .
C1_6 C 0.2792(2) 1.5988(4) 0.6087(2) 0.0478(8) Uani 1 1 d . . . . .
B1_6 B 0.2526(2) 1.3299(4) 0.5685(2) 0.0383(8) Uani 1 1 d . . . . .
N2_6 N 0.21171(18) 1.5704(3) 0.57666(15) 0.0414(6) Uani 1 1 d . . . . .
C2_6 C 0.3446(2) 1.5130(4) 0.61976(18) 0.0442(8) Uani 1 1 d . . . . .
C3_6 C 0.4172(2) 1.5589(4) 0.6487(2) 0.0502(9) Uani 1 1 d . . . . .
H3_6 H 0.422781 1.646796 0.662734 0.060 Uiso 1 1 calc R U . . .
C4_6 C 0.4797(2) 1.4751(5) 0.6563(2) 0.0578(11) Uani 1 1 d . . . . .
H4_6 H 0.528370 1.505432 0.675696 0.069 Uiso 1 1 calc R U . . .
C5_6 C 0.4720(2) 1.3468(4) 0.6357(2) 0.0568(10) Uani 1 1 d . . . . .
H5_6 H 0.515502 1.289865 0.640614 0.068 Uiso 1 1 calc R U . . .
C6_6 C 0.4015(2) 1.3021(4) 0.6084(2) 0.0501(9) Uani 1 1 d . . . . .
H6_6 H 0.396948 1.213796 0.594959 0.060 Uiso 1 1 calc R U . . .
C7_6 C 0.3362(2) 1.3831(4) 0.59964(18) 0.0433(8) Uani 1 1 d . . . . .
C1_7 C 0.1211(2) 1.4360(3) 0.52181(18) 0.0382(7) Uani 1 1 d . . . . .
C2_7 C 0.0933(2) 1.3138(3) 0.50079(17) 0.0413(7) Uani 1 1 d . . . . .
H2_7 H 0.125570 1.239896 0.508158 0.050 Uiso 1 1 calc R U . . .
C3_7 C 0.0185(2) 1.2997(4) 0.4691(2) 0.0493(8) Uani 1 1 d . . . . .
H3_7 H 0.000147 1.216208 0.455643 0.059 Uiso 1 1 calc R U . . .
C4_7 C -0.0291(2) 1.4067(5) 0.4570(2) 0.0537(9) Uani 1 1 d . . . . .
H4_7 H -0.079808 1.397565 0.435282 0.064 Uiso 1 1 calc R U . . .
C5_7 C -0.0008(2) 1.5269(4) 0.4774(2) 0.0580(10) Uani 1 1 d . . . . .
H5_7 H -0.032926 1.600820 0.469459 0.070 Uiso 1 1 calc R U . . .
C6_7 C 0.0725(2) 1.5425(4) 0.5089(2) 0.0505(9) Uani 1 1 d . . . . .
H6_7 H 0.090169 1.626531 0.522040 0.061 Uiso 1 1 calc R U . . .
C1_8 C 0.21427(18) 1.2282(3) 0.62407(17) 0.0346(6) Uani 1 1 d . . . . .
C2_8 C 0.16116(18) 1.2710(3) 0.67453(17) 0.0349(6) Uani 1 1 d . . . . .
H2_8 H 0.143921 1.358238 0.672884 0.042 Uiso 1 1 calc R U . . .
C3_8 C 0.1330(2) 1.1897(3) 0.72681(18) 0.0409(7) Uani 1 1 d . . . . .
H3_8 H 0.097023 1.221854 0.760266 0.049 Uiso 1 1 calc R U . . .
C4_8 C 0.1568(2) 1.0624(3) 0.73062(19) 0.0430(8) Uani 1 1 d . . . . .
H4_8 H 0.137720 1.006814 0.766657 0.052 Uiso 1 1 calc R U . . .
C5_8 C 0.2087(2) 1.0167(3) 0.6813(2) 0.0448(8) Uani 1 1 d . . . . .
H5_8 H 0.225133 0.928990 0.682982 0.054 Uiso 1 1 calc R U . . .
C6_8 C 0.2370(2) 1.0986(3) 0.62934(18) 0.0406(7) Uani 1 1 d . . . . .
H6_8 H 0.273029 1.065590 0.596182 0.049 Uiso 1 1 calc R U . . .
O1_9 O 0.3217(2) 1.1261(3) 0.40806(16) 0.0667(8) Uani 1 1 d . . . . .
N1_9 N 0.26747(18) 1.2586(3) 0.49637(15) 0.0432(7) Uani 1 1 d . . . . .
C1_9 C 0.2955(2) 1.1923(3) 0.4540(2) 0.0463(8) Uani 1 1 d . . . . .
N1_10 N 0.34024(16) 0.6403(3) 0.36300(14) 0.0373(6) Uani 1 1 d . . . . .
C1_10 C 0.3789(2) 0.7376(3) 0.31349(19) 0.0415(7) Uani 1 1 d . . . . .
H1A_10 H 0.408581 0.688879 0.277644 0.050 Uiso 1 1 calc R U . . .
H1B_10 H 0.337055 0.785885 0.287169 0.050 Uiso 1 1 calc R U . . .
C2_10 C 0.4334(2) 0.8338(3) 0.3491(2) 0.0472(8) Uani 1 1 d . . . . .
H2A_10 H 0.474071 0.787704 0.378131 0.057 Uiso 1 1 calc R U . . .
H2B_10 H 0.403729 0.889972 0.381535 0.057 Uiso 1 1 calc R U . . .
C3_10 C 0.4722(2) 0.9166(3) 0.2922(2) 0.0492(9) Uani 1 1 d . . . . .
H3A_10 H 0.512181 0.971829 0.316576 0.059 Uiso 1 1 calc R U . . .
H3B_10 H 0.500042 0.858116 0.259606 0.059 Uiso 1 1 calc R U . . .
C4_10 C 0.4189(2) 1.0025(4) 0.2472(2) 0.0566(10) Uani 1 1 d . . . . .
H4A_10 H 0.450320 1.056255 0.215866 0.085 Uiso 1 1 calc R U . . .
H4B_10 H 0.388646 1.058143 0.278640 0.085 Uiso 1 1 calc R U . . .
H4C_10 H 0.382956 0.948946 0.217970 0.085 Uiso 1 1 calc R U . . .
C5_10 C 0.30194(19) 0.7068(4) 0.42502(18) 0.0405(7) Uani 1 1 d . . . . .
H5A_10 H 0.280644 0.639561 0.456754 0.049 Uiso 1 1 calc R U . . .
H5B_10 H 0.342862 0.754245 0.453021 0.049 Uiso 1 1 calc R U . . .
C6_10 C 0.2370(2) 0.7999(4) 0.4052(2) 0.0483(8) Uani 1 1 d . . . . .
H6A_10 H 0.191439 0.752071 0.384632 0.058 Uiso 1 1 calc R U . . .
H6B_10 H 0.255017 0.861716 0.368761 0.058 Uiso 1 1 calc R U . . .
C7_10 C 0.2132(2) 0.8729(3) 0.47184(19) 0.0438(8) Uani 1 1 d . . . . .
H7A_10 H 0.199310 0.810099 0.509400 0.053 Uiso 1 1 calc R U . . .
H7B_10 H 0.258205 0.924594 0.490394 0.053 Uiso 1 1 calc R U . . .
C8_10 C 0.1442(2) 0.9617(4) 0.4564(2) 0.0575(10) Uani 1 1 d . . . . .
H8A_10 H 0.134476 1.014310 0.498904 0.086 Uiso 1 1 calc R U . . .
H8B_10 H 0.097590 0.909887 0.444336 0.086 Uiso 1 1 calc R U . . .
H8C_10 H 0.155812 1.018406 0.416064 0.086 Uiso 1 1 calc R U . . .
C13_10 C 0.3976(2) 0.5439(3) 0.3966(2) 0.0433(8) Uani 1 1 d . . . . .
H13A_10 H 0.436201 0.592172 0.426828 0.052 Uiso 1 1 calc R U . . .
H13B_10 H 0.368356 0.486336 0.428661 0.052 Uiso 1 1 calc R U . . .
C14_10 C 0.4419(3) 0.4603(4) 0.3450(3) 0.0638(11) Uani 1 1 d . . . . .
H14A_10 H 0.404567 0.426698 0.307847 0.077 Uiso 1 1 calc R U . . .
H14B_10 H 0.480650 0.514697 0.320674 0.077 Uiso 1 1 calc R U . . .
C15_10 C 0.4832(3) 0.3498(6) 0.3798(3) 0.0702(13) Uani 1 1 d . . . . .
H15A_10 H 0.443444 0.291578 0.399885 0.084 Uiso 1 1 calc R U . . .
H15B_10 H 0.515684 0.383488 0.420501 0.084 Uiso 1 1 calc R U . . .
C16_10 C 0.5343(3) 0.2719(4) 0.3333(3) 0.0639(11) Uani 1 1 d . . . . .
H16A_10 H 0.547932 0.190424 0.357477 0.096 Uiso 1 1 calc R U . . .
H16B_10 H 0.582195 0.320390 0.324113 0.096 Uiso 1 1 calc R U . . .
H16C_10 H 0.506408 0.253381 0.287794 0.096 Uiso 1 1 calc R U . . .
C9_10 C 0.2835(7) 0.5698(13) 0.3132(8) 0.0359(19) Uani 0.728(9) 1 d . U P A 1
H9A_10 H 0.242383 0.631742 0.297104 0.043 Uiso 0.728(9) 1 calc R U P A 1
H9B_10 H 0.311992 0.543199 0.270242 0.043 Uiso 0.728(9) 1 calc R U P A 1
C10_10 C 0.2437(3) 0.4524(5) 0.3425(3) 0.0398(11) Uani 0.728(9) 1 d . U P A 1
H10A_10 H 0.220174 0.473563 0.388834 0.048 Uiso 0.728(9) 1 calc R U P A 1
H10B_10 H 0.282532 0.382439 0.350794 0.048 Uiso 0.728(9) 1 calc R U P A 1
C11_10 C 0.1806(4) 0.4078(6) 0.2892(4) 0.0454(13) Uani 0.728(9) 1 d . U P A 1
H11A_10 H 0.138163 0.473091 0.287205 0.054 Uiso 0.728(9) 1 calc R U P A 1
H11B_10 H 0.203039 0.403046 0.241048 0.054 Uiso 0.728(9) 1 calc R U P A 1
C12_10 C 0.1458(4) 0.2780(6) 0.3071(3) 0.0572(16) Uani 0.728(9) 1 d . U P A 1
H12A_10 H 0.105588 0.255096 0.270734 0.086 Uiso 0.728(9) 1 calc R U P A 1
H12B_10 H 0.187138 0.212216 0.308026 0.086 Uiso 0.728(9) 1 calc R U P A 1
H12C_10 H 0.122195 0.282333 0.354230 0.086 Uiso 0.728(9) 1 calc R U P A 1
C9_101 C 0.271(2) 0.581(4) 0.319(2) 0.036(3) Uani 0.272(9) 1 d . U P A 2
H9A_101 H 0.238809 0.651458 0.297468 0.043 Uiso 0.272(9) 1 calc R U P A 2
H9B_101 H 0.291150 0.527985 0.279853 0.043 Uiso 0.272(9) 1 calc R U P A 2
C10_101 C 0.2174(9) 0.4958(15) 0.3646(8) 0.041(2) Uani 0.272(9) 1 d . U P A 2
H10A_101 H 0.188796 0.550894 0.398353 0.050 Uiso 0.272(9) 1 calc R U P A 2
H10B_101 H 0.249951 0.434074 0.393048 0.050 Uiso 0.272(9) 1 calc R U P A 2
C11_101 C 0.1578(10) 0.4201(15) 0.3160(10) 0.043(3) Uani 0.272(9) 1 d . U P A 2
H11A_101 H 0.113016 0.392477 0.344672 0.052 Uiso 0.272(9) 1 calc R U P A 2
H11B_101 H 0.137560 0.477335 0.277166 0.052 Uiso 0.272(9) 1 calc R U P A 2
C12_101 C 0.1964(11) 0.3008(16) 0.2831(9) 0.059(4) Uani 0.272(9) 1 d . U P A 2
H12A_101 H 0.157783 0.254652 0.252761 0.088 Uiso 0.272(9) 1 calc R U P A 2
H12B_101 H 0.240232 0.328195 0.254115 0.088 Uiso 0.272(9) 1 calc R U P A 2
H12C_101 H 0.215718 0.243442 0.321537 0.088 Uiso 0.272(9) 1 calc R U P A 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
B1_1 N1_1 1.562(4) . ?
B1_1 N1_4 1.570(4) . ?
B1_1 C7_1 1.614(4) . ?
B1_1 C1_3 1.629(5) . ?
C2_1 C3_1 1.387(4) . ?
C2_1 C7_1 1.395(4) . ?
C2_1 C1_1 1.464(5) . ?
N1_1 N3_1 1.365(3) . ?
N1_1 C1_2 1.415(4) . ?
C1_1 N3_1 1.287(4) . ?
C3_1 C4_1 1.365(5) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.386(5) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.388(5) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.412(4) . ?
C6_1 H6_1 0.9500 . ?
C1_2 C2_2 1.390(4) . ?
C1_2 C6_2 1.404(4) . ?
C2_2 C3_2 1.391(5) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.401(5) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.382(5) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.381(5) . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
C1_3 C6_3 1.400(4) . ?
C1_3 C2_3 1.403(4) . ?
C2_3 C3_3 1.391(5) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.366(6) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.394(6) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.385(4) . ?
C5_3 H5_3 0.9500 . ?
C6_3 H6_3 0.9500 . ?
O1_4 C2_4 1.195(4) . ?
N1_4 C2_4 1.163(4) . ?
N1_5 C5_5 1.516(4) . ?
N1_5 C9_5 1.524(4) . ?
N1_5 C13_5 1.524(4) . ?
N1_5 C1_5 1.539(4) . ?
C1_5 C2_5 1.525(5) . ?
C1_5 H1A_5 0.9900 . ?
C1_5 H1B_5 0.9900 . ?
C2_5 C3_5 1.529(5) . ?
C2_5 H2A_5 0.9900 . ?
C2_5 H2B_5 0.9900 . ?
C3_5 C4_5 1.510(5) . ?
C3_5 H3A_5 0.9900 . ?
C3_5 H3B_5 0.9900 . ?
C4_5 H4A_5 0.9800 . ?
C4_5 H4B_5 0.9800 . ?
C4_5 H4C_5 0.9800 . ?
C5_5 C6_5 1.511(5) . ?
C5_5 H5A_5 0.9900 . ?
C5_5 H5B_5 0.9900 . ?
C6_5 C7_5 1.524(5) . ?
C6_5 H6A_5 0.9900 . ?
C6_5 H6B_5 0.9900 . ?
C7_5 C8_5 1.515(6) . ?
C7_5 H7A_5 0.9900 . ?
C7_5 H7B_5 0.9900 . ?
C8_5 H8A_5 0.9800 . ?
C8_5 H8B_5 0.9800 . ?
C8_5 H8C_5 0.9800 . ?
C9_5 C10_5 1.523(5) . ?
C9_5 H9A_5 0.9900 . ?
C9_5 H9B_5 0.9900 . ?
C10_5 C11_5 1.549(5) . ?
C10_5 H10A_5 0.9900 . ?
C10_5 H10B_5 0.9900 . ?
C11_5 C12_5 1.490(7) . ?
C11_5 H11A_5 0.9900 . ?
C11_5 H11B_5 0.9900 . ?
C12_5 H12A_5 0.9800 . ?
C12_5 H12B_5 0.9800 . ?
C12_5 H12C_5 0.9800 . ?
C13_5 C14_5 1.500(5) . ?
C13_5 H13A_5 0.9900 . ?
C13_5 H13B_5 0.9900 . ?
C14_5 C15_5 1.531(5) . ?
C14_5 H14A_5 0.9900 . ?
C14_5 H14B_5 0.9900 . ?
C15_5 C16_5 1.510(5) . ?
C15_5 H15A_5 0.9900 . ?
C15_5 H15B_5 0.9900 . ?
C16_5 H16A_5 0.9800 . ?
C16_5 H16B_5 0.9800 . ?
C16_5 H16C_5 0.9800 . ?
N1_6 N2_6 1.356(4) . ?
N1_6 C1_7 1.422(4) . ?
N1_6 B1_6 1.562(5) . ?
C1_6 N2_6 1.316(5) . ?
C1_6 C2_6 1.437(5) . ?
B1_6 N1_9 1.562(5) . ?
B1_6 C7_6 1.621(5) . ?
B1_6 C1_8 1.629(5) . ?
C2_6 C7_6 1.402(5) . ?
C2_6 C3_6 1.419(5) . ?
C3_6 C4_6 1.379(6) . ?
C3_6 H3_6 0.9500 . ?
C4_6 C5_6 1.386(7) . ?
C4_6 H4_6 0.9500 . ?
C5_6 C6_6 1.374(6) . ?
C5_6 H5_6 0.9500 . ?
C6_6 C7_6 1.400(5) . ?
C6_6 H6_6 0.9500 . ?
C1_7 C6_7 1.396(5) . ?
C1_7 C2_7 1.402(5) . ?
C2_7 C3_7 1.399(5) . ?
C2_7 H2_7 0.9500 . ?
C3_7 C4_7 1.387(6) . ?
C3_7 H3_7 0.9500 . ?
C4_7 C5_7 1.384(6) . ?
C4_7 H4_7 0.9500 . ?
C5_7 C6_7 1.376(6) . ?
C5_7 H5_7 0.9500 . ?
C6_7 H6_7 0.9500 . ?
C1_8 C6_8 1.399(4) . ?
C1_8 C2_8 1.400(4) . ?
C2_8 C3_8 1.386(4) . ?
C2_8 H2_8 0.9500 . ?
C3_8 C4_8 1.380(5) . ?
C3_8 H3_8 0.9500 . ?
C4_8 C5_8 1.382(5) . ?
C4_8 H4_8 0.9500 . ?
C5_8 C6_8 1.386(5) . ?
C5_8 H5_8 0.9500 . ?
C6_8 H6_8 0.9500 . ?
O1_9 C1_9 1.195(4) . ?
N1_9 C1_9 1.162(5) . ?
N1_10 C9_10 1.510(15) . ?
N1_10 C5_10 1.513(4) . ?
N1_10 C13_10 1.519(5) . ?
N1_10 C1_10 1.531(4) . ?
N1_10 C9_101 1.55(4) . ?
C1_10 C2_10 1.503(5) . ?
C1_10 H1A_10 0.9900 . ?
C1_10 H1B_10 0.9900 . ?
C2_10 C3_10 1.532(5) . ?
C2_10 H2A_10 0.9900 . ?
C2_10 H2B_10 0.9900 . ?
C3_10 C4_10 1.509(6) . ?
C3_10 H3A_10 0.9900 . ?
C3_10 H3B_10 0.9900 . ?
C4_10 H4A_10 0.9800 . ?
C4_10 H4B_10 0.9800 . ?
C4_10 H4C_10 0.9800 . ?
C5_10 C6_10 1.507(5) . ?
C5_10 H5A_10 0.9900 . ?
C5_10 H5B_10 0.9900 . ?
C6_10 C7_10 1.520(5) . ?
C6_10 H6A_10 0.9900 . ?
C6_10 H6B_10 0.9900 . ?
C7_10 C8_10 1.516(5) . ?
C7_10 H7A_10 0.9900 . ?
C7_10 H7B_10 0.9900 . ?
C8_10 H8A_10 0.9800 . ?
C8_10 H8B_10 0.9800 . ?
C8_10 H8C_10 0.9800 . ?
C13_10 C14_10 1.514(5) . ?
C13_10 H13A_10 0.9900 . ?
C13_10 H13B_10 0.9900 . ?
C14_10 C15_10 1.483(6) . ?
C14_10 H14A_10 0.9900 . ?
C14_10 H14B_10 0.9900 . ?
C15_10 C16_10 1.488(6) . ?
C15_10 H15A_10 0.9900 . ?
C15_10 H15B_10 0.9900 . ?
C16_10 H16A_10 0.9800 . ?
C16_10 H16B_10 0.9800 . ?
C16_10 H16C_10 0.9800 . ?
C9_10 C10_10 1.503(15) . ?
C9_10 H9A_10 0.9900 . ?
C9_10 H9B_10 0.9900 . ?
C10_10 C11_10 1.516(7) . ?
C10_10 H10A_10 0.9900 . ?
C10_10 H10B_10 0.9900 . ?
C11_10 C12_10 1.511(9) . ?
C11_10 H11A_10 0.9900 . ?
C11_10 H11B_10 0.9900 . ?
C12_10 H12A_10 0.9800 . ?
C12_10 H12B_10 0.9800 . ?
C12_10 H12C_10 0.9800 . ?
C9_101 C10_101 1.54(4) . ?
C9_101 H9A_101 0.9900 . ?
C9_101 H9B_101 0.9900 . ?
C10_101 C11_101 1.55(2) . ?
C10_101 H10A_101 0.9900 . ?
C10_101 H10B_101 0.9900 . ?
C11_101 C12_101 1.54(2) . ?
C11_101 H11A_101 0.9900 . ?
C11_101 H11B_101 0.9900 . ?
C12_101 H12A_101 0.9800 . ?
C12_101 H12B_101 0.9800 . ?
C12_101 H12C_101 0.9800 . ?

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
N1_1 B1_1 N1_4 108.7(3) . . ?
N1_1 B1_1 C7_1 108.5(2) . . ?
N1_4 B1_1 C7_1 107.9(2) . . ?
N1_1 B1_1 C1_3 111.8(3) . . ?
N1_4 B1_1 C1_3 109.4(2) . . ?
C7_1 B1_1 C1_3 110.6(2) . . ?
C3_1 C2_1 C7_1 121.9(3) . . ?
C3_1 C2_1 C1_1 120.9(3) . . ?
C7_1 C2_1 C1_1 117.2(3) . . ?
N3_1 N1_1 C1_2 111.9(2) . . ?
N3_1 N1_1 B1_1 124.9(2) . . ?
C1_2 N1_1 B1_1 123.3(2) . . ?
N3_1 C1_1 C2_1 127.1(3) . . ?
C1_1 N3_1 N1_1 120.4(3) . . ?
C4_1 C3_1 C2_1 120.5(3) . . ?
C4_1 C3_1 H3_1 119.7 . . ?
C2_1 C3_1 H3_1 119.7 . . ?
C3_1 C4_1 C5_1 119.6(3) . . ?
C3_1 C4_1 H4_1 120.2 . . ?
C5_1 C4_1 H4_1 120.2 . . ?
C4_1 C5_1 C6_1 120.3(3) . . ?
C4_1 C5_1 H5_1 119.8 . . ?
C6_1 C5_1 H5_1 119.8 . . ?
C5_1 C6_1 C7_1 121.1(3) . . ?
C5_1 C6_1 H6_1 119.4 . . ?
C7_1 C6_1 H6_1 119.4 . . ?
C2_1 C7_1 C6_1 116.5(3) . . ?
C2_1 C7_1 B1_1 121.8(3) . . ?
C6_1 C7_1 B1_1 121.6(3) . . ?
C2_2 C1_2 C6_2 117.5(3) . . ?
C2_2 C1_2 N1_1 120.6(3) . . ?
C6_2 C1_2 N1_1 121.9(3) . . ?
C1_2 C2_2 C3_2 121.5(3) . . ?
C1_2 C2_2 H2_2 119.2 . . ?
C3_2 C2_2 H2_2 119.2 . . ?
C2_2 C3_2 C4_2 120.4(3) . . ?
C2_2 C3_2 H3_2 119.8 . . ?
C4_2 C3_2 H3_2 119.8 . . ?
C5_2 C4_2 C3_2 118.0(3) . . ?
C5_2 C4_2 H4_2 121.0 . . ?
C3_2 C4_2 H4_2 121.0 . . ?
C6_2 C5_2 C4_2 121.7(3) . . ?
C6_2 C5_2 H5_2 119.1 . . ?
C4_2 C5_2 H5_2 119.1 . . ?
C5_2 C6_2 C1_2 120.8(3) . . ?
C5_2 C6_2 H6_2 119.6 . . ?
C1_2 C6_2 H6_2 119.6 . . ?
C6_3 C1_3 C2_3 116.1(3) . . ?
C6_3 C1_3 B1_1 120.9(3) . . ?
C2_3 C1_3 B1_1 122.8(3) . . ?
C3_3 C2_3 C1_3 121.5(3) . . ?
C3_3 C2_3 H2_3 119.2 . . ?
C1_3 C2_3 H2_3 119.2 . . ?
C4_3 C3_3 C2_3 121.0(3) . . ?
C4_3 C3_3 H3_3 119.5 . . ?
C2_3 C3_3 H3_3 119.5 . . ?
C3_3 C4_3 C5_3 119.2(3) . . ?
C3_3 C4_3 H4_3 120.4 . . ?
C5_3 C4_3 H4_3 120.4 . . ?
C6_3 C5_3 C4_3 119.7(3) . . ?
C6_3 C5_3 H5_3 120.2 . . ?
C4_3 C5_3 H5_3 120.2 . . ?
C5_3 C6_3 C1_3 122.5(3) . . ?
C5_3 C6_3 H6_3 118.7 . . ?
C1_3 C6_3 H6_3 118.7 . . ?
C2_4 N1_4 B1_1 159.2(3) . . ?
N1_4 C2_4 O1_4 177.8(4) . . ?
C5_5 N1_5 C9_5 111.1(2) . . ?
C5_5 N1_5 C13_5 107.1(2) . . ?
C9_5 N1_5 C13_5 110.8(2) . . ?
C5_5 N1_5 C1_5 110.5(2) . . ?
C9_5 N1_5 C1_5 106.9(2) . . ?
C13_5 N1_5 C1_5 110.5(2) . . ?
C2_5 C1_5 N1_5 115.0(3) . . ?
C2_5 C1_5 H1A_5 108.5 . . ?
N1_5 C1_5 H1A_5 108.5 . . ?
C2_5 C1_5 H1B_5 108.5 . . ?
N1_5 C1_5 H1B_5 108.5 . . ?
H1A_5 C1_5 H1B_5 107.5 . . ?
C1_5 C2_5 C3_5 111.7(3) . . ?
C1_5 C2_5 H2A_5 109.3 . . ?
C3_5 C2_5 H2A_5 109.3 . . ?
C1_5 C2_5 H2B_5 109.3 . . ?
C3_5 C2_5 H2B_5 109.3 . . ?
H2A_5 C2_5 H2B_5 108.0 . . ?
C4_5 C3_5 C2_5 114.5(3) . . ?
C4_5 C3_5 H3A_5 108.6 . . ?
C2_5 C3_5 H3A_5 108.6 . . ?
C4_5 C3_5 H3B_5 108.6 . . ?
C2_5 C3_5 H3B_5 108.6 . . ?
H3A_5 C3_5 H3B_5 107.6 . . ?
C3_5 C4_5 H4A_5 109.5 . . ?
C3_5 C4_5 H4B_5 109.5 . . ?
H4A_5 C4_5 H4B_5 109.5 . . ?
C3_5 C4_5 H4C_5 109.5 . . ?
H4A_5 C4_5 H4C_5 109.5 . . ?
H4B_5 C4_5 H4C_5 109.5 . . ?
C6_5 C5_5 N1_5 116.2(3) . . ?
C6_5 C5_5 H5A_5 108.2 . . ?
N1_5 C5_5 H5A_5 108.2 . . ?
C6_5 C5_5 H5B_5 108.2 . . ?
N1_5 C5_5 H5B_5 108.2 . . ?
H5A_5 C5_5 H5B_5 107.4 . . ?
C5_5 C6_5 C7_5 110.4(3) . . ?
C5_5 C6_5 H6A_5 109.6 . . ?
C7_5 C6_5 H6A_5 109.6 . . ?
C5_5 C6_5 H6B_5 109.6 . . ?
C7_5 C6_5 H6B_5 109.6 . . ?
H6A_5 C6_5 H6B_5 108.1 . . ?
C8_5 C7_5 C6_5 112.5(3) . . ?
C8_5 C7_5 H7A_5 109.1 . . ?
C6_5 C7_5 H7A_5 109.1 . . ?
C8_5 C7_5 H7B_5 109.1 . . ?
C6_5 C7_5 H7B_5 109.1 . . ?
H7A_5 C7_5 H7B_5 107.8 . . ?
C7_5 C8_5 H8A_5 109.5 . . ?
C7_5 C8_5 H8B_5 109.5 . . ?
H8A_5 C8_5 H8B_5 109.5 . . ?
C7_5 C8_5 H8C_5 109.5 . . ?
H8A_5 C8_5 H8C_5 109.5 . . ?
H8B_5 C8_5 H8C_5 109.5 . . ?
C10_5 C9_5 N1_5 115.0(3) . . ?
C10_5 C9_5 H9A_5 108.5 . . ?
N1_5 C9_5 H9A_5 108.5 . . ?
C10_5 C9_5 H9B_5 108.5 . . ?
N1_5 C9_5 H9B_5 108.5 . . ?
H9A_5 C9_5 H9B_5 107.5 . . ?
C9_5 C10_5 C11_5 110.1(3) . . ?
C9_5 C10_5 H10A_5 109.6 . . ?
C11_5 C10_5 H10A_5 109.6 . . ?
C9_5 C10_5 H10B_5 109.6 . . ?
C11_5 C10_5 H10B_5 109.6 . . ?
H10A_5 C10_5 H10B_5 108.2 . . ?
C12_5 C11_5 C10_5 113.6(3) . . ?
C12_5 C11_5 H11A_5 108.8 . . ?
C10_5 C11_5 H11A_5 108.8 . . ?
C12_5 C11_5 H11B_5 108.8 . . ?
C10_5 C11_5 H11B_5 108.8 . . ?
H11A_5 C11_5 H11B_5 107.7 . . ?
C11_5 C12_5 H12A_5 109.5 . . ?
C11_5 C12_5 H12B_5 109.5 . . ?
H12A_5 C12_5 H12B_5 109.5 . . ?
C11_5 C12_5 H12C_5 109.5 . . ?
H12A_5 C12_5 H12C_5 109.5 . . ?
H12B_5 C12_5 H12C_5 109.5 . . ?
C14_5 C13_5 N1_5 116.3(3) . . ?
C14_5 C13_5 H13A_5 108.2 . . ?
N1_5 C13_5 H13A_5 108.2 . . ?
C14_5 C13_5 H13B_5 108.2 . . ?
N1_5 C13_5 H13B_5 108.2 . . ?
H13A_5 C13_5 H13B_5 107.4 . . ?
C13_5 C14_5 C15_5 111.5(3) . . ?
C13_5 C14_5 H14A_5 109.3 . . ?
C15_5 C14_5 H14A_5 109.3 . . ?
C13_5 C14_5 H14B_5 109.3 . . ?
C15_5 C14_5 H14B_5 109.3 . . ?
H14A_5 C14_5 H14B_5 108.0 . . ?
C16_5 C15_5 C14_5 115.1(3) . . ?
C16_5 C15_5 H15A_5 108.5 . . ?
C14_5 C15_5 H15A_5 108.5 . . ?
C16_5 C15_5 H15B_5 108.5 . . ?
C14_5 C15_5 H15B_5 108.5 . . ?
H15A_5 C15_5 H15B_5 107.5 . . ?
C15_5 C16_5 H16A_5 109.5 . . ?
C15_5 C16_5 H16B_5 109.5 . . ?
H16A_5 C16_5 H16B_5 109.5 . . ?
C15_5 C16_5 H16C_5 109.5 . . ?
H16A_5 C16_5 H16C_5 109.5 . . ?
H16B_5 C16_5 H16C_5 109.5 . . ?
N2_6 N1_6 C1_7 111.5(3) . . ?
N2_6 N1_6 B1_6 125.0(3) . . ?
C1_7 N1_6 B1_6 123.1(3) . . ?
N2_6 C1_6 C2_6 126.4(3) . . ?
N1_6 B1_6 N1_9 109.5(3) . . ?
N1_6 B1_6 C7_6 108.5(3) . . ?
N1_9 B1_6 C7_6 107.7(3) . . ?
N1_6 B1_6 C1_8 111.2(3) . . ?
N1_9 B1_6 C1_8 108.9(3) . . ?
C7_6 B1_6 C1_8 111.0(3) . . ?
C1_6 N2_6 N1_6 119.9(3) . . ?
C7_6 C2_6 C3_6 120.3(4) . . ?
C7_6 C2_6 C1_6 118.8(3) . . ?
C3_6 C2_6 C1_6 121.0(4) . . ?
C4_6 C3_6 C2_6 119.5(4) . . ?
C4_6 C3_6 H3_6 120.2 . . ?
C2_6 C3_6 H3_6 120.2 . . ?
C3_6 C4_6 C5_6 120.5(4) . . ?
C3_6 C4_6 H4_6 119.7 . . ?
C5_6 C4_6 H4_6 119.7 . . ?
C6_6 C5_6 C4_6 119.9(4) . . ?
C6_6 C5_6 H5_6 120.0 . . ?
C4_6 C5_6 H5_6 120.0 . . ?
C5_6 C6_6 C7_6 121.9(4) . . ?
C5_6 C6_6 H6_6 119.1 . . ?
C7_6 C6_6 H6_6 119.1 . . ?
C6_6 C7_6 C2_6 117.9(3) . . ?
C6_6 C7_6 B1_6 121.9(3) . . ?
C2_6 C7_6 B1_6 120.2(3) . . ?
C6_7 C1_7 C2_7 118.0(3) . . ?
C6_7 C1_7 N1_6 122.4(3) . . ?
C2_7 C1_7 N1_6 119.6(3) . . ?
C3_7 C2_7 C1_7 120.6(3) . . ?
C3_7 C2_7 H2_7 119.7 . . ?
C1_7 C2_7 H2_7 119.7 . . ?
C4_7 C3_7 C2_7 120.6(4) . . ?
C4_7 C3_7 H3_7 119.7 . . ?
C2_7 C3_7 H3_7 119.7 . . ?
C5_7 C4_7 C3_7 118.4(4) . . ?
C5_7 C4_7 H4_7 120.8 . . ?
C3_7 C4_7 H4_7 120.8 . . ?
C6_7 C5_7 C4_7 121.9(4) . . ?
C6_7 C5_7 H5_7 119.1 . . ?
C4_7 C5_7 H5_7 119.1 . . ?
C5_7 C6_7 C1_7 120.6(4) . . ?
C5_7 C6_7 H6_7 119.7 . . ?
C1_7 C6_7 H6_7 119.7 . . ?
C6_8 C1_8 C2_8 116.1(3) . . ?
C6_8 C1_8 B1_6 123.2(3) . . ?
C2_8 C1_8 B1_6 120.5(3) . . ?
C3_8 C2_8 C1_8 121.9(3) . . ?
C3_8 C2_8 H2_8 119.0 . . ?
C1_8 C2_8 H2_8 119.0 . . ?
C4_8 C3_8 C2_8 120.5(3) . . ?
C4_8 C3_8 H3_8 119.8 . . ?
C2_8 C3_8 H3_8 119.8 . . ?
C3_8 C4_8 C5_8 119.1(3) . . ?
C3_8 C4_8 H4_8 120.5 . . ?
C5_8 C4_8 H4_8 120.5 . . ?
C4_8 C5_8 C6_8 120.2(3) . . ?
C4_8 C5_8 H5_8 119.9 . . ?
C6_8 C5_8 H5_8 119.9 . . ?
C5_8 C6_8 C1_8 122.2(3) . . ?
C5_8 C6_8 H6_8 118.9 . . ?
C1_8 C6_8 H6_8 118.9 . . ?
C1_9 N1_9 B1_6 161.2(3) . . ?
N1_9 C1_9 O1_9 176.9(4) . . ?
C9_10 N1_10 C5_10 113.9(5) . . ?
C9_10 N1_10 C13_10 109.3(5) . . ?
C5_10 N1_10 C13_10 105.7(3) . . ?
C9_10 N1_10 C1_10 103.1(6) . . ?
C5_10 N1_10 C1_10 111.6(3) . . ?
C13_10 N1_10 C1_10 113.3(3) . . ?
C5_10 N1_10 C9_101 103.9(13) . . ?
C13_10 N1_10 C9_101 115.6(16) . . ?
C1_10 N1_10 C9_101 106.4(16) . . ?
C2_10 C1_10 N1_10 116.2(3) . . ?
C2_10 C1_10 H1A_10 108.2 . . ?
N1_10 C1_10 H1A_10 108.2 . . ?
C2_10 C1_10 H1B_10 108.2 . . ?
N1_10 C1_10 H1B_10 108.2 . . ?
H1A_10 C1_10 H1B_10 107.4 . . ?
C1_10 C2_10 C3_10 109.8(3) . . ?
C1_10 C2_10 H2A_10 109.7 . . ?
C3_10 C2_10 H2A_10 109.7 . . ?
C1_10 C2_10 H2B_10 109.7 . . ?
C3_10 C2_10 H2B_10 109.7 . . ?
H2A_10 C2_10 H2B_10 108.2 . . ?
C4_10 C3_10 C2_10 116.6(3) . . ?
C4_10 C3_10 H3A_10 108.1 . . ?
C2_10 C3_10 H3A_10 108.1 . . ?
C4_10 C3_10 H3B_10 108.1 . . ?
C2_10 C3_10 H3B_10 108.1 . . ?
H3A_10 C3_10 H3B_10 107.3 . . ?
C3_10 C4_10 H4A_10 109.5 . . ?
C3_10 C4_10 H4B_10 109.5 . . ?
H4A_10 C4_10 H4B_10 109.5 . . ?
C3_10 C4_10 H4C_10 109.5 . . ?
H4A_10 C4_10 H4C_10 109.5 . . ?
H4B_10 C4_10 H4C_10 109.5 . . ?
C6_10 C5_10 N1_10 115.9(3) . . ?
C6_10 C5_10 H5A_10 108.3 . . ?
N1_10 C5_10 H5A_10 108.3 . . ?
C6_10 C5_10 H5B_10 108.3 . . ?
N1_10 C5_10 H5B_10 108.3 . . ?
H5A_10 C5_10 H5B_10 107.4 . . ?
C5_10 C6_10 C7_10 109.3(3) . . ?
C5_10 C6_10 H6A_10 109.8 . . ?
C7_10 C6_10 H6A_10 109.8 . . ?
C5_10 C6_10 H6B_10 109.8 . . ?
C7_10 C6_10 H6B_10 109.8 . . ?
H6A_10 C6_10 H6B_10 108.3 . . ?
C8_10 C7_10 C6_10 111.8(3) . . ?
C8_10 C7_10 H7A_10 109.2 . . ?
C6_10 C7_10 H7A_10 109.2 . . ?
C8_10 C7_10 H7B_10 109.2 . . ?
C6_10 C7_10 H7B_10 109.2 . . ?
H7A_10 C7_10 H7B_10 107.9 . . ?
C7_10 C8_10 H8A_10 109.5 . . ?
C7_10 C8_10 H8B_10 109.5 . . ?
H8A_10 C8_10 H8B_10 109.5 . . ?
C7_10 C8_10 H8C_10 109.5 . . ?
H8A_10 C8_10 H8C_10 109.5 . . ?
H8B_10 C8_10 H8C_10 109.5 . . ?
C14_10 C13_10 N1_10 116.1(3) . . ?
C14_10 C13_10 H13A_10 108.3 . . ?
N1_10 C13_10 H13A_10 108.3 . . ?
C14_10 C13_10 H13B_10 108.3 . . ?
N1_10 C13_10 H13B_10 108.3 . . ?
H13A_10 C13_10 H13B_10 107.4 . . ?
C15_10 C14_10 C13_10 113.7(4) . . ?
C15_10 C14_10 H14A_10 108.8 . . ?
C13_10 C14_10 H14A_10 108.8 . . ?
C15_10 C14_10 H14B_10 108.8 . . ?
C13_10 C14_10 H14B_10 108.8 . . ?
H14A_10 C14_10 H14B_10 107.7 . . ?
C14_10 C15_10 C16_10 116.3(4) . . ?
C14_10 C15_10 H15A_10 108.2 . . ?
C16_10 C15_10 H15A_10 108.2 . . ?
C14_10 C15_10 H15B_10 108.2 . . ?
C16_10 C15_10 H15B_10 108.2 . . ?
H15A_10 C15_10 H15B_10 107.4 . . ?
C15_10 C16_10 H16A_10 109.5 . . ?
C15_10 C16_10 H16B_10 109.5 . . ?
H16A_10 C16_10 H16B_10 109.5 . . ?
C15_10 C16_10 H16C_10 109.5 . . ?
H16A_10 C16_10 H16C_10 109.5 . . ?
H16B_10 C16_10 H16C_10 109.5 . . ?
C10_10 C9_10 N1_10 117.0(10) . . ?
C10_10 C9_10 H9A_10 108.0 . . ?
N1_10 C9_10 H9A_10 108.0 . . ?
C10_10 C9_10 H9B_10 108.0 . . ?
N1_10 C9_10 H9B_10 108.0 . . ?
H9A_10 C9_10 H9B_10 107.3 . . ?
C9_10 C10_10 C11_10 109.1(7) . . ?
C9_10 C10_10 H10A_10 109.9 . . ?
C11_10 C10_10 H10A_10 109.9 . . ?
C9_10 C10_10 H10B_10 109.9 . . ?
C11_10 C10_10 H10B_10 109.9 . . ?
H10A_10 C10_10 H10B_10 108.3 . . ?
C12_10 C11_10 C10_10 113.7(5) . . ?
C12_10 C11_10 H11A_10 108.8 . . ?
C10_10 C11_10 H11A_10 108.8 . . ?
C12_10 C11_10 H11B_10 108.8 . . ?
C10_10 C11_10 H11B_10 108.8 . . ?
H11A_10 C11_10 H11B_10 107.7 . . ?
C11_10 C12_10 H12A_10 109.5 . . ?
C11_10 C12_10 H12B_10 109.5 . . ?
H12A_10 C12_10 H12B_10 109.5 . . ?
C11_10 C12_10 H12C_10 109.5 . . ?
H12A_10 C12_10 H12C_10 109.5 . . ?
H12B_10 C12_10 H12C_10 109.5 . . ?
C10_101 C9_101 N1_10 113(3) . . ?
C10_101 C9_101 H9A_101 108.9 . . ?
N1_10 C9_101 H9A_101 108.9 . . ?
C10_101 C9_101 H9B_101 108.9 . . ?
N1_10 C9_101 H9B_101 108.9 . . ?
H9A_101 C9_101 H9B_101 107.7 . . ?
C9_101 C10_101 C11_101 110.7(19) . . ?
C9_101 C10_101 H10A_101 109.5 . . ?
C11_101 C10_101 H10A_101 109.5 . . ?
C9_101 C10_101 H10B_101 109.5 . . ?
C11_101 C10_101 H10B_101 109.5 . . ?
H10A_101 C10_101 H10B_101 108.1 . . ?
C12_101 C11_101 C10_101 110.9(13) . . ?
C12_101 C11_101 H11A_101 109.5 . . ?
C10_101 C11_101 H11A_101 109.5 . . ?
C12_101 C11_101 H11B_101 109.5 . . ?
C10_101 C11_101 H11B_101 109.5 . . ?
H11A_101 C11_101 H11B_101 108.0 . . ?
C11_101 C12_101 H12A_101 109.5 . . ?
C11_101 C12_101 H12B_101 109.5 . . ?
H12A_101 C12_101 H12B_101 109.5 . . ?
C11_101 C12_101 H12C_101 109.5 . . ?
H12A_101 C12_101 H12C_101 109.5 . . ?
H12B_101 C12_101 H12C_101 109.5 . . ?

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_4 B1_1 N1_1 N3_1 114.4(3) . . . . ?
C7_1 B1_1 N1_1 N3_1 -2.7(4) . . . . ?
C1_3 B1_1 N1_1 N3_1 -124.9(3) . . . . ?
N1_4 B1_1 N1_1 C1_2 -64.6(4) . . . . ?
C7_1 B1_1 N1_1 C1_2 178.4(3) . . . . ?
C1_3 B1_1 N1_1 C1_2 56.2(4) . . . . ?
C3_1 C2_1 C1_1 N3_1 179.8(4) . . . . ?
C7_1 C2_1 C1_1 N3_1 -1.7(6) . . . . ?
C2_1 C1_1 N3_1 N1_1 -1.7(6) . . . . ?
C1_2 N1_1 N3_1 C1_1 -176.9(3) . . . . ?
B1_1 N1_1 N3_1 C1_1 4.0(5) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.3(5) . . . . ?
C1_1 C2_1 C3_1 C4_1 178.7(4) . . . . ?
C2_1 C3_1 C4_1 C5_1 -1.6(6) . . . . ?
C3_1 C4_1 C5_1 C6_1 2.1(6) . . . . ?
C4_1 C5_1 C6_1 C7_1 -1.4(5) . . . . ?
C3_1 C2_1 C7_1 C6_1 0.5(5) . . . . ?
C1_1 C2_1 C7_1 C6_1 -178.1(3) . . . . ?
C3_1 C2_1 C7_1 B1_1 -178.8(3) . . . . ?
C1_1 C2_1 C7_1 B1_1 2.7(4) . . . . ?
C5_1 C6_1 C7_1 C2_1 0.1(5) . . . . ?
C5_1 C6_1 C7_1 B1_1 179.3(3) . . . . ?
N1_1 B1_1 C7_1 C2_1 -0.7(4) . . . . ?
N1_4 B1_1 C7_1 C2_1 -118.3(3) . . . . ?
C1_3 B1_1 C7_1 C2_1 122.2(3) . . . . ?
N1_1 B1_1 C7_1 C6_1 -180.0(3) . . . . ?
N1_4 B1_1 C7_1 C6_1 62.5(4) . . . . ?
C1_3 B1_1 C7_1 C6_1 -57.1(4) . . . . ?
N3_1 N1_1 C1_2 C2_2 -176.1(3) . . . . ?
B1_1 N1_1 C1_2 C2_2 3.0(5) . . . . ?
N3_1 N1_1 C1_2 C6_2 5.0(4) . . . . ?
B1_1 N1_1 C1_2 C6_2 -175.9(3) . . . . ?
C6_2 C1_2 C2_2 C3_2 -0.5(5) . . . . ?
N1_1 C1_2 C2_2 C3_2 -179.4(3) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.3(5) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.1(5) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.3(5) . . . . ?
C4_2 C5_2 C6_2 C1_2 0.1(5) . . . . ?
C2_2 C1_2 C6_2 C5_2 0.3(5) . . . . ?
N1_1 C1_2 C6_2 C5_2 179.2(3) . . . . ?
N1_1 B1_1 C1_3 C6_3 27.8(4) . . . . ?
N1_4 B1_1 C1_3 C6_3 148.2(3) . . . . ?
C7_1 B1_1 C1_3 C6_3 -93.2(3) . . . . ?
N1_1 B1_1 C1_3 C2_3 -157.7(3) . . . . ?
N1_4 B1_1 C1_3 C2_3 -37.3(4) . . . . ?
C7_1 B1_1 C1_3 C2_3 81.3(4) . . . . ?
C6_3 C1_3 C2_3 C3_3 0.2(5) . . . . ?
B1_1 C1_3 C2_3 C3_3 -174.5(3) . . . . ?
C1_3 C2_3 C3_3 C4_3 -0.3(5) . . . . ?
C2_3 C3_3 C4_3 C5_3 -0.2(6) . . . . ?
C3_3 C4_3 C5_3 C6_3 0.9(5) . . . . ?
C4_3 C5_3 C6_3 C1_3 -1.0(5) . . . . ?
C2_3 C1_3 C6_3 C5_3 0.4(4) . . . . ?
B1_1 C1_3 C6_3 C5_3 175.3(3) . . . . ?
N1_1 B1_1 N1_4 C2_4 153.5(8) . . . . ?
C7_1 B1_1 N1_4 C2_4 -89.1(9) . . . . ?
C1_3 B1_1 N1_4 C2_4 31.3(10) . . . . ?
C5_5 N1_5 C1_5 C2_5 61.7(3) . . . . ?
C9_5 N1_5 C1_5 C2_5 -177.3(3) . . . . ?
C13_5 N1_5 C1_5 C2_5 -56.6(3) . . . . ?
N1_5 C1_5 C2_5 C3_5 178.3(3) . . . . ?
C1_5 C2_5 C3_5 C4_5 -66.5(4) . . . . ?
C9_5 N1_5 C5_5 C6_5 -54.1(4) . . . . ?
C13_5 N1_5 C5_5 C6_5 -175.3(3) . . . . ?
C1_5 N1_5 C5_5 C6_5 64.3(3) . . . . ?
N1_5 C5_5 C6_5 C7_5 -165.7(3) . . . . ?
C5_5 C6_5 C7_5 C8_5 -174.8(3) . . . . ?
C5_5 N1_5 C9_5 C10_5 -65.7(4) . . . . ?
C13_5 N1_5 C9_5 C10_5 53.2(4) . . . . ?
C1_5 N1_5 C9_5 C10_5 173.7(3) . . . . ?
N1_5 C9_5 C10_5 C11_5 172.6(3) . . . . ?
C9_5 C10_5 C11_5 C12_5 -80.3(4) . . . . ?
C5_5 N1_5 C13_5 C14_5 -178.3(3) . . . . ?
C9_5 N1_5 C13_5 C14_5 60.4(3) . . . . ?
C1_5 N1_5 C13_5 C14_5 -57.9(3) . . . . ?
N1_5 C13_5 C14_5 C15_5 175.6(3) . . . . ?
C13_5 C14_5 C15_5 C16_5 66.7(4) . . . . ?
N2_6 N1_6 B1_6 N1_9 -129.0(3) . . . . ?
C1_7 N1_6 B1_6 N1_9 58.3(4) . . . . ?
N2_6 N1_6 B1_6 C7_6 -11.7(4) . . . . ?
C1_7 N1_6 B1_6 C7_6 175.6(3) . . . . ?
N2_6 N1_6 B1_6 C1_8 110.7(3) . . . . ?
C1_7 N1_6 B1_6 C1_8 -62.1(4) . . . . ?
C2_6 C1_6 N2_6 N1_6 3.9(5) . . . . ?
C1_7 N1_6 N2_6 C1_6 179.1(3) . . . . ?
B1_6 N1_6 N2_6 C1_6 5.6(5) . . . . ?
N2_6 C1_6 C2_6 C7_6 -4.8(5) . . . . ?
N2_6 C1_6 C2_6 C3_6 173.5(3) . . . . ?
C7_6 C2_6 C3_6 C4_6 0.6(5) . . . . ?
C1_6 C2_6 C3_6 C4_6 -177.7(3) . . . . ?
C2_6 C3_6 C4_6 C5_6 0.1(6) . . . . ?
C3_6 C4_6 C5_6 C6_6 -0.7(6) . . . . ?
C4_6 C5_6 C6_6 C7_6 0.6(6) . . . . ?
C5_6 C6_6 C7_6 C2_6 0.1(5) . . . . ?
C5_6 C6_6 C7_6 B1_6 -179.0(3) . . . . ?
C3_6 C2_6 C7_6 C6_6 -0.7(5) . . . . ?
C1_6 C2_6 C7_6 C6_6 177.7(3) . . . . ?
C3_6 C2_6 C7_6 B1_6 178.4(3) . . . . ?
C1_6 C2_6 C7_6 B1_6 -3.2(5) . . . . ?
N1_6 B1_6 C7_6 C6_6 -170.9(3) . . . . ?
N1_9 B1_6 C7_6 C6_6 -52.4(4) . . . . ?
C1_8 B1_6 C7_6 C6_6 66.7(4) . . . . ?
N1_6 B1_6 C7_6 C2_6 10.0(4) . . . . ?
N1_9 B1_6 C7_6 C2_6 128.5(3) . . . . ?
C1_8 B1_6 C7_6 C2_6 -112.4(3) . . . . ?
N2_6 N1_6 C1_7 C6_7 6.6(4) . . . . ?
B1_6 N1_6 C1_7 C6_7 -179.7(3) . . . . ?
N2_6 N1_6 C1_7 C2_7 -174.5(3) . . . . ?
B1_6 N1_6 C1_7 C2_7 -0.8(4) . . . . ?
C6_7 C1_7 C2_7 C3_7 -1.1(5) . . . . ?
N1_6 C1_7 C2_7 C3_7 180.0(3) . . . . ?
C1_7 C2_7 C3_7 C4_7 0.8(5) . . . . ?
C2_7 C3_7 C4_7 C5_7 -0.3(6) . . . . ?
C3_7 C4_7 C5_7 C6_7 0.0(6) . . . . ?
C4_7 C5_7 C6_7 C1_7 -0.4(6) . . . . ?
C2_7 C1_7 C6_7 C5_7 0.9(5) . . . . ?
N1_6 C1_7 C6_7 C5_7 179.8(3) . . . . ?
N1_6 B1_6 C1_8 C6_8 159.1(3) . . . . ?
N1_9 B1_6 C1_8 C6_8 38.3(4) . . . . ?
C7_6 B1_6 C1_8 C6_8 -80.0(4) . . . . ?
N1_6 B1_6 C1_8 C2_8 -27.2(4) . . . . ?
N1_9 B1_6 C1_8 C2_8 -147.9(3) . . . . ?
C7_6 B1_6 C1_8 C2_8 93.7(4) . . . . ?
C6_8 C1_8 C2_8 C3_8 0.2(5) . . . . ?
B1_6 C1_8 C2_8 C3_8 -174.0(3) . . . . ?
C1_8 C2_8 C3_8 C4_8 -0.1(5) . . . . ?
C2_8 C3_8 C4_8 C5_8 -0.4(5) . . . . ?
C3_8 C4_8 C5_8 C6_8 0.7(5) . . . . ?
C4_8 C5_8 C6_8 C1_8 -0.6(5) . . . . ?
C2_8 C1_8 C6_8 C5_8 0.1(5) . . . . ?
B1_6 C1_8 C6_8 C5_8 174.1(3) . . . . ?
N1_6 B1_6 N1_9 C1_9 161.8(10) . . . . ?
C7_6 B1_6 N1_9 C1_9 44.0(12) . . . . ?
C1_8 B1_6 N1_9 C1_9 -76.4(12) . . . . ?
C9_10 N1_10 C1_10 C2_10 173.7(5) . . . . ?
C5_10 N1_10 C1_10 C2_10 51.0(4) . . . . ?
C13_10 N1_10 C1_10 C2_10 -68.3(4) . . . . ?
C9_101 N1_10 C1_10 C2_10 163.6(14) . . . . ?
N1_10 C1_10 C2_10 C3_10 175.4(3) . . . . ?
C1_10 C2_10 C3_10 C4_10 64.5(4) . . . . ?
C9_10 N1_10 C5_10 C6_10 -54.9(7) . . . . ?
C13_10 N1_10 C5_10 C6_10 -175.0(3) . . . . ?
C1_10 N1_10 C5_10 C6_10 61.4(4) . . . . ?
C9_101 N1_10 C5_10 C6_10 -52.9(17) . . . . ?
N1_10 C5_10 C6_10 C7_10 -171.6(3) . . . . ?
C5_10 C6_10 C7_10 C8_10 -176.1(3) . . . . ?
C9_10 N1_10 C13_10 C14_10 54.8(6) . . . . ?
C5_10 N1_10 C13_10 C14_10 177.8(3) . . . . ?
C1_10 N1_10 C13_10 C14_10 -59.6(4) . . . . ?
C9_101 N1_10 C13_10 C14_10 63.6(16) . . . . ?
N1_10 C13_10 C14_10 C15_10 -167.2(4) . . . . ?
C13_10 C14_10 C15_10 C16_10 -174.0(4) . . . . ?
C5_10 N1_10 C9_10 C10_10 -67.9(8) . . . . ?
C13_10 N1_10 C9_10 C10_10 50.2(8) . . . . ?
C1_10 N1_10 C9_10 C10_10 171.0(6) . . . . ?
N1_10 C9_10 C10_10 C11_10 171.4(6) . . . . ?
C9_10 C10_10 C11_10 C12_10 170.3(6) . . . . ?
C5_10 N1_10 C9_101 C10_101 -53(3) . . . . ?
C13_10 N1_10 C9_101 C10_101 62(3) . . . . ?
C1_10 N1_10 C9_101 C10_101 -171.2(19) . . . . ?
N1_10 C9_101 C10_101 C11_101 -170.0(18) . . . . ?
C9_101 C10_101 C11_101 C12_101 80(2) . . . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-CN
_database_code_depnum_ccdc_archive 'CCDC 2394206'
loop_
_audit_author_name
_audit_author_address
'Tim Wellnitz'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.5e (K.Radacki, 2005-23)'
_audit_creation_date             2024-10-05
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C20 H15 B N3, C16 H36 N'
_chemical_formula_sum            'C36 H51 B N4'
_chemical_formula_weight         550.61
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'


_cell_length_a                   9.5035(2)
_cell_length_b                   18.6014(4)
_cell_length_c                   19.0874(2)
_cell_angle_alpha                87.7410(10)
_cell_angle_beta                 87.4770(10)
_cell_angle_gamma                78.256(2)
_cell_volume                     3298.80(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    28327
_cell_measurement_theta_min      3.2990
_cell_measurement_theta_max      71.9980

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0263
2 1 1 0.0628
-1 -1 0 0.0525
0 -1 1 0.0207
1 12 1 0.0195
1 -6 -11 0.0290
-1 5 11 0.0285
0 -12 0 0.0143
-1 -12 0 0.0117
0 12 0 0.0163

_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.986
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     57.00  83.00   0.50    9.95    --   38.00  44.00  75.06   52
  2  ω    -91.00 -64.00   0.50    9.95    --  -46.00 -41.00 -92.70   54
  3  ω    -95.00 -67.00   0.50    9.95    --  -50.00 -40.00-173.20   56
  4  ω    -99.00 -72.00   0.50    9.95    --  -54.00 -44.00-134.40   54
  5  ω   -100.00 -71.00   0.50    9.95    --  -54.00 -33.00  97.45   58
  6  ω   -100.00 -71.00   0.50    9.95    --  -54.00 -33.00 -51.59   58
  7  ω   -103.00 -76.00   0.50    9.95    --  -58.00 -44.00 170.67   54
  8  ω   -103.00 -76.00   0.50    9.95    --  -58.00 -42.00-105.60   54
  9  ω   -103.00 -76.00   0.50    9.95    --  -58.00 -43.00 140.02   54
 10  ω    -82.00 -21.00   0.50    9.95    --  -61.72 125.00   0.00  122
 11  ω   -107.00 -80.00   0.50    9.95    --  -62.00 -43.00  36.56   54
 12  ω   -111.00 -84.00   0.50    9.95    --  -66.00 -42.00  66.58   54
 13  ω   -115.00 -88.00   0.50    9.95    --  -70.00 -43.00  93.40   54
 14  ω   -116.00 -88.00   0.50    9.95    --  -70.00 -41.00   1.37   56
 15  ω    -92.00 -31.00   0.50    9.95    --  -71.97 125.00-180.00  122
 16  ω   -120.00 -90.00   0.50    9.95    --  -74.00 -31.00-157.62   60
 17  ω   -120.00 -90.00   0.50    9.95    --  -74.00 -31.00 -58.75   60
 18  ω    -95.00 -34.00   0.50    9.95    --  -75.12 125.00-150.00  122
 19  ω    -95.00 -34.00   0.50    9.95    --  -75.12 125.00 120.00  122
 20  ω    -95.00 -34.00   0.50    9.95    --  -75.12 125.00  30.00  122
 21  ω     36.00  97.00   0.50    9.95    --   76.61-125.00  60.00  122
 22  ω   -106.00 -36.00   0.50    9.95    --  -78.00 136.00  22.33  140
 23  ω   -120.00 -93.00   0.50    9.95    --  -78.50-121.00 137.82   54
 24  ω   -125.00 -96.00   0.50    9.95    --  -78.50 -41.00-113.64   58
 25  ω   -124.00 -80.00   0.50    9.95    --  -78.50 -20.00 -26.96   88
 26  ω   -126.00 -93.00   0.50    9.95    --  -78.50 -28.00 -78.41   66
 27  ω    -87.00 -39.00   0.50    9.95    --  -78.50 107.00 -82.81   96
 28  ω   -101.00 -37.00   0.50    9.95    --  -78.50 128.00  -3.65  128
 29  ω   -108.00 -37.00   0.50    9.95    --  -78.50 138.00  27.15  142
 30  ω   -124.00 -73.00   0.50    9.95    --  -78.50 -19.00 137.02  102
 31  ω   -123.00 -97.00   0.50    9.95    --  -78.50 -44.00  46.94   52
 32  ω   -108.00 -38.00   0.50    9.95    --  -78.50 139.00 175.21  140
 33  ω   -108.00 -37.00   0.50    9.95    --  -78.50 138.00-130.79  142
 34  ω   -126.00 -94.00   0.50    9.95    --  -78.50 -29.00  14.27   64
 35  ω   -108.00 -37.00   0.50    9.95    --  -78.50 138.00 129.73  142
 36  ω   -108.00 -37.00   0.50    9.95    --  -78.50 138.00-130.79  142
 37  ω   -107.00 -37.00   0.50    9.95    --  -78.50 137.00 -60.91  140
 38  ω   -126.00 -94.00   0.50    9.95    --  -78.50 -29.00 130.54   64
 39  ω   -101.00 -37.00   0.50    9.95    --  -78.50 128.00-137.76  128
 40  ω   -108.00 -38.00   0.50    9.95    --  -78.50 139.00 -84.40  140
 41  ω   -126.00 -95.00   0.50    9.95    --  -78.50 -31.00-174.30   62
 42  ω   -125.00 -88.00   0.50    9.95    --  -78.50 -24.00 103.13   74
 43  ω   -107.00 -37.00   0.50    9.95    --  -78.50 137.00  61.34  140
 44  ω   -126.00 -95.00   0.50    9.95    --  -78.50 -31.00  90.49   62
 45  ω   -124.00 -80.00   0.50    9.95    --  -78.50 -20.00  25.97   88
 46  ω   -103.00 -37.00   0.50    9.95    --  -78.50 131.00 175.27  132
 47  ω   -107.00 -37.00   0.50    9.95    --  -78.50 137.00 -60.91  140
 48  ω     39.00 101.00   0.50    9.95    --   80.50-126.00  48.29  124
 49  ω     40.00  96.00   0.50    9.95    --   80.50-117.00 -14.26  112
 50  ω     39.00 100.00   0.50    9.95    --   80.50-123.00-165.63  122
 51  ω     33.00  59.00   0.50    9.95    --   14.00  46.00 163.40   52
 52  ω     33.00  59.00   0.50    9.95    --   14.00  46.00 -81.58   52
 53  ω     33.00  59.00   0.50    9.95    --   14.00  46.00  72.65   52
 54  ω    -36.00 -10.00   0.50    9.95    --  -18.00 121.00  63.40   52
 55  ω     37.00  63.00   0.50    9.95    --   18.00  46.00  18.88   52
 56  ω    -71.00 -44.00   0.50    9.95    --  -26.00 -44.00  49.95   54
 57  ω    -75.00 -48.00   0.50    9.95    --  -30.00 -42.00 137.84   54
 58  ω    -79.00 -51.00   0.50    9.95    --  -34.00 -40.00 -84.99   56
 59  ω    -88.00 -59.00   0.50    9.95    --  -42.00 -39.00  -9.95   58
 60  ω   -116.00 -87.00   0.50    9.95    --  -70.00 -39.00 -94.00   58
 61  ω   -119.00 -92.00   0.50    9.95    --  -74.00 -44.00 117.84   54
 62  ω   -119.00 -91.00   0.50    9.95    --  -74.00 -40.00  -7.54   56
 63  ω   -109.00 -69.00   0.50    9.95    --  -78.50 140.00  89.43   80
 64  ω   -123.00 -97.00   0.50    9.95    --  -78.50 -44.00  79.86   52
 65  ω   -123.00 -97.00   0.50    9.95    --  -78.50 -44.00-131.20   52
 66  ω   -125.00 -94.00   0.50    9.95    --  -78.50 -30.00-105.20   62
 67  ω   -126.00 -95.00   0.50    9.95    --  -78.50 -31.00 -37.32   62
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0903382000
_diffrn_orient_matrix_UB_12      -0.0537135000
_diffrn_orient_matrix_UB_13      -0.0519703000
_diffrn_orient_matrix_UB_21      0.1380720000
_diffrn_orient_matrix_UB_22      0.0075412000
_diffrn_orient_matrix_UB_23      0.0359217000
_diffrn_orient_matrix_UB_31      -0.0150295000
_diffrn_orient_matrix_UB_32      -0.0649655000
_diffrn_orient_matrix_UB_33      0.0504177000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            77310
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.305
_diffrn_reflns_theta_max         74.350
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             12859
_reflns_number_gt                9509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal class for the 
 calculation of statistics and refinement. _reflns_Friedel_fraction is 
 defined as the number of unique Friedel pairs measured divided by the number 
 that would be possible theoretically, ignoring centric projections and 
 systematic absences.
;

_computing_data_collection       
;
 CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))
;
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_structure_solution    "SHELXT 2018/2 (Sheldrick, 2018)'"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          
;
 One diazaborinine molecule with a phenyl substituent is disordered. The 
 disordered part is refined isotropically and is constrained using AFIX 6. A 
 constant Uii value of 0.04864 and 0.04855 for the phenyl substituent, 
 which was obtained by free refinement of Uii with a free variabel using 
 SIMU with esd = 0.0001 for the whole diazaborinin molecule. One n-butyl 
 group is highly disordered and refined isotropically. The distances between 
 the disordered n-butyl group atoms C9 to C10, C10 to C11, C11 to C12 and C9 
 to C11, C10 to C12 were restrained to the value of 1.533 (esd = 0.002) and 
 2.547 (esd = 0.005). (Bonham, Bartell, Kohl, 1959) The distances between 
 atoms N1_9 to C9_9, N1_9 to C9_91, N1_9 to C9_911, N1_9 to C9_9111 were 
 restrained during refinement to the same value using SADI.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1189P)²+1.0791P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12859
_refine_ls_number_parameters     775
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.2161
_refine_ls_wR_factor_gt          0.2027
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.050
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_1 N 0.5568(2) 0.82517(11) 0.35093(10) 0.0444(4) Uani 1 1 d . . . . .
C1_1 C 0.6884(3) 0.75046(16) 0.43363(14) 0.0552(6) Uani 1 1 d . . . . .
H1_1 H 0.760821 0.744429 0.467349 0.066 Uiso 1 1 calc R U . . .
B1_1 B 0.4340(3) 0.78097(15) 0.35110(15) 0.0441(6) Uani 1 1 d . . . . .
N2_1 N 0.6666(2) 0.81109(12) 0.39763(11) 0.0509(5) Uani 1 1 d . . . . .
C2_1 C 0.6137(3) 0.68954(14) 0.42834(14) 0.0520(6) Uani 1 1 d . . . . .
C3_1 C 0.6679(3) 0.62100(17) 0.46044(15) 0.0622(7) Uani 1 1 d . . . . .
H3_1 H 0.751055 0.614580 0.487732 0.075 Uiso 1 1 calc R U . . .
C4_1 C 0.6014(3) 0.56345(16) 0.45251(16) 0.0669(8) Uani 1 1 d . . . . .
H4_1 H 0.637718 0.517016 0.474388 0.080 Uiso 1 1 calc R U . . .
C5_1 C 0.4797(3) 0.57333(15) 0.41200(16) 0.0625(7) Uani 1 1 d . . . . .
H5_1 H 0.431765 0.533919 0.406485 0.075 Uiso 1 1 calc R U . . .
C6_1 C 0.4302(3) 0.64085(14) 0.38020(15) 0.0541(6) Uani 1 1 d . . . . .
H6_1 H 0.348268 0.646816 0.352121 0.065 Uiso 1 1 calc R U . . .
C7_1 C 0.4944(3) 0.70050(13) 0.38730(13) 0.0472(5) Uani 1 1 d . . . . .
N1_2 N 0.3696(2) 0.75107(12) 0.21766(11) 0.0516(5) Uani 1 1 d . . . . .
C1_2 C 0.3979(2) 0.76691(12) 0.27218(13) 0.0412(5) Uani 1 1 d . . . . .
C1_3 C 0.5567(3) 0.88989(12) 0.31024(12) 0.0442(5) Uani 1 1 d . . . . .
C2_3 C 0.6822(3) 0.91956(14) 0.30105(14) 0.0527(6) Uani 1 1 d . . . . .
H2_3 H 0.768012 0.896275 0.323121 0.063 Uiso 1 1 calc R U . . .
C3_3 C 0.6794(3) 0.98286(14) 0.25965(15) 0.0565(6) Uani 1 1 d . . . . .
H3_3 H 0.763995 1.002672 0.254187 0.068 Uiso 1 1 calc R U . . .
C4_3 C 0.5581(3) 1.01750(14) 0.22646(14) 0.0541(6) Uani 1 1 d . . . . .
H4_3 H 0.558371 1.060590 0.198084 0.065 Uiso 1 1 calc R U . . .
C5_3 C 0.4358(3) 0.98879(14) 0.23494(13) 0.0506(6) Uani 1 1 d . . . . .
H5_3 H 0.350859 1.012588 0.212393 0.061 Uiso 1 1 calc R U . . .
C6_3 C 0.4344(2) 0.92570(12) 0.27585(12) 0.0440(5) Uani 1 1 d . . . . .
H6_3 H 0.348971 0.906585 0.280528 0.053 Uiso 1 1 calc R U . . .
C1_4 C 0.2869(2) 0.82316(12) 0.39164(12) 0.0423(5) Uani 1 1 d . . . . .
C2_4 C 0.1541(2) 0.80432(14) 0.38258(14) 0.0485(6) Uani 1 1 d . . . . .
H2_4 H 0.148178 0.768056 0.349761 0.058 Uiso 1 1 calc R U . . .
C3_4 C 0.0299(3) 0.83696(15) 0.42010(15) 0.0551(6) Uani 1 1 d . . . . .
H3_4 H -0.058769 0.822794 0.412705 0.066 Uiso 1 1 calc R U . . .
C4_4 C 0.0357(3) 0.88976(14) 0.46790(14) 0.0554(6) Uani 1 1 d . . . . .
H4_4 H -0.048525 0.911883 0.493865 0.066 Uiso 1 1 calc R U . . .
C5_4 C 0.1647(3) 0.91021(14) 0.47774(13) 0.0531(6) Uani 1 1 d . . . . .
H5_4 H 0.169301 0.946902 0.510334 0.064 Uiso 1 1 calc R U . . .
C6_4 C 0.2882(3) 0.87741(13) 0.44021(12) 0.0461(5) Uani 1 1 d . . . . .
H6_4 H 0.376142 0.892253 0.447764 0.055 Uiso 1 1 calc R U . . .
N1_5 N 0.1349(2) 0.65964(11) 0.83016(12) 0.0423(5) Uani 0.874(3) 1 d D . P A 1
C1_5 C -0.0989(3) 0.72285(16) 0.81804(18) 0.0578(8) Uani 0.874(3) 1 d . . P A 1
H1_5 H -0.190882 0.723330 0.800211 0.069 Uiso 0.874(3) 1 calc R U P A 1
B1_5 B 0.1678(3) 0.70961(16) 0.88842(17) 0.0413(7) Uani 0.874(3) 1 d D . P A 1
N2_5 N 0.0027(3) 0.66670(13) 0.80189(15) 0.0528(7) Uani 0.874(3) 1 d . . P A 1
C2_5 C -0.0875(3) 0.78411(15) 0.85977(16) 0.0474(7) Uani 0.874(3) 1 d . . P A 1
C3_5 C -0.2024(3) 0.84528(18) 0.86593(19) 0.0539(8) Uani 0.874(3) 1 d . . P A 1
H3_5 H -0.291755 0.844777 0.845682 0.065 Uiso 0.874(3) 1 calc R U P A 1
C4_5 C -0.1845(4) 0.90569(17) 0.9014(2) 0.0541(8) Uani 0.874(3) 1 d . . P A 1
H4_5 H -0.262029 0.946660 0.906165 0.065 Uiso 0.874(3) 1 calc R U P A 1
C5_5 C -0.0554(4) 0.90676(17) 0.92984(18) 0.0531(7) Uani 0.874(3) 1 d . . P A 1
H5_5 H -0.042576 0.949078 0.953059 0.064 Uiso 0.874(3) 1 calc R U P A 1
C6_5 C 0.0571(3) 0.84615(15) 0.92488(16) 0.0473(6) Uani 0.874(3) 1 d . . P A 1
H6_5 H 0.145715 0.847518 0.945470 0.057 Uiso 0.874(3) 1 calc R U P A 1
C7_5 C 0.0433(3) 0.78385(15) 0.89066(14) 0.0409(6) Uani 0.874(3) 1 d . . P A 1
B1_51 B 0.2240(11) 0.6666(5) 0.8700(5) 0.049 Uiso 0.126(3) 1 d DG U P A 2
N1_51 N 0.0796(11) 0.7012(4) 0.8411(6) 0.049 Uiso 0.126(3) 1 d DG U P A 2
N2_51 N 0.0197(10) 0.6782(6) 0.7788(6) 0.049 Uiso 0.126(3) 1 d G U P A 2
C1_51 C 0.0845(11) 0.6130(6) 0.7566(6) 0.049 Uiso 0.126(3) 1 d G U P A 2
H1_51 H 0.038814 0.593837 0.720374 0.058 Uiso 0.126(3) 1 calc R U P A 2
C2_51 C 0.2187(11) 0.5662(4) 0.7810(5) 0.049 Uiso 0.126(3) 1 d G U P A 2
C3_51 C 0.2770(16) 0.5007(6) 0.7451(8) 0.049 Uiso 0.126(3) 1 d G U P A 2
H3_51 H 0.229336 0.487700 0.706228 0.058 Uiso 0.126(3) 1 calc R U P A 2
C4_51 C 0.3927(16) 0.4593(6) 0.7650(9) 0.049 Uiso 0.126(3) 1 d G U P A 2
H4_51 H 0.431847 0.416065 0.740259 0.058 Uiso 0.126(3) 1 calc R U P A 2
C5_51 C 0.4662(13) 0.4775(6) 0.8253(9) 0.049 Uiso 0.126(3) 1 d G U P A 2
H5_51 H 0.550173 0.445274 0.841384 0.058 Uiso 0.126(3) 1 calc R U P A 2
C6_51 C 0.4118(10) 0.5422(6) 0.8587(7) 0.049 Uiso 0.126(3) 1 d G U P A 2
H6_51 H 0.460435 0.555146 0.897268 0.058 Uiso 0.126(3) 1 calc R U P A 2
C7_51 C 0.2866(9) 0.5889(4) 0.8368(5) 0.049 Uiso 0.126(3) 1 d G U P A 2
C1_6 C 0.2279(3) 0.59331(13) 0.81194(14) 0.0407(6) Uani 0.874(3) 1 d D . P A 1
C2_6 C 0.1945(3) 0.54956(15) 0.75935(15) 0.0477(7) Uani 0.874(3) 1 d . . P A 1
H2_6 H 0.108285 0.564856 0.734667 0.057 Uiso 0.874(3) 1 calc R U P A 1
C3_6 C 0.2874(4) 0.48378(17) 0.74328(19) 0.0566(8) Uani 0.874(3) 1 d . . P A 1
H3_6 H 0.263890 0.454859 0.707297 0.068 Uiso 0.874(3) 1 calc R U P A 1
C4_6 C 0.4152(4) 0.45920(17) 0.77910(18) 0.0541(9) Uani 0.874(3) 1 d . . P A 1
H4_6 H 0.477366 0.413776 0.768615 0.065 Uiso 0.874(3) 1 calc R U P A 1
C5_6 C 0.4471(3) 0.50311(16) 0.82974(18) 0.0520(7) Uani 0.874(3) 1 d . . P A 1
H5_6 H 0.533405 0.487853 0.854328 0.062 Uiso 0.874(3) 1 calc R U P A 1
C6_6 C 0.3567(3) 0.56907(15) 0.84595(15) 0.0455(6) Uani 0.874(3) 1 d . . P A 1
H6_6 H 0.382869 0.598378 0.880896 0.055 Uiso 0.874(3) 1 calc R U P A 1
C1_61 C -0.0127(17) 0.7675(6) 0.8600(9) 0.049 Uiso 0.126(3) 1 d DG U P A 2
C2_61 C 0.0398(13) 0.8200(9) 0.8952(10) 0.049 Uiso 0.126(3) 1 d G U P A 2
H2_61 H 0.138639 0.811686 0.905707 0.058 Uiso 0.126(3) 1 calc R U P A 2
C3_61 C -0.0524(19) 0.8846(8) 0.9149(11) 0.049 Uiso 0.126(3) 1 d G U P A 2
H3_61 H -0.016548 0.920467 0.938924 0.058 Uiso 0.126(3) 1 calc R U P A 2
C4_61 C -0.1971(18) 0.8967(8) 0.8995(13) 0.049 Uiso 0.126(3) 1 d G U P A 2
H4_61 H -0.260100 0.940874 0.912959 0.058 Uiso 0.126(3) 1 calc R U P A 2
C5_61 C -0.2496(14) 0.8442(9) 0.8643(12) 0.049 Uiso 0.126(3) 1 d G U P A 2
H5_61 H -0.348466 0.852501 0.853776 0.058 Uiso 0.126(3) 1 calc R U P A 2
C6_61 C -0.1574(19) 0.7796(7) 0.8446(8) 0.049 Uiso 0.126(3) 1 d G U P A 2
H6_61 H -0.193280 0.743719 0.820558 0.058 Uiso 0.126(3) 1 calc R U P A 2
C1_7 C 0.1772(2) 0.66570(13) 0.96395(13) 0.0443(5) Uani 1 1 d D . . . .
C2_7 C 0.1073(2) 0.60702(12) 0.97768(12) 0.0424(5) Uani 1 1 d . . . . .
H2_7 H 0.059814 0.590003 0.940813 0.051 Uiso 1 1 calc R U . . .
C3_7 C 0.1054(2) 0.57307(13) 1.04346(13) 0.0460(5) Uani 1 1 d . . . . .
H3_7 H 0.056650 0.533509 1.051409 0.055 Uiso 1 1 calc R U . . .
C4_7 C 0.1745(3) 0.59689(13) 1.09748(13) 0.0485(6) Uani 1 1 d . . . . .
H4_7 H 0.174838 0.573256 1.142531 0.058 Uiso 1 1 calc R U . . .
C5_7 C 0.2433(3) 0.65528(14) 1.08583(14) 0.0503(6) Uani 1 1 d . . . . .
H5_7 H 0.290195 0.672244 1.122945 0.060 Uiso 1 1 calc R U . . .
C6_7 C 0.2436(3) 0.68869(13) 1.02012(14) 0.0482(6) Uani 1 1 d . . . . .
H6_7 H 0.290808 0.728881 1.012890 0.058 Uiso 1 1 calc R U . . .
N1_8 N 0.4204(2) 0.75927(12) 0.85396(12) 0.0542(5) Uani 1 1 d . . . . .
C1_8 C 0.3200(3) 0.73441(13) 0.86820(13) 0.0481(5) Uani 1 1 d D . . . .
N1_9 N 0.3782(2) 0.73814(11) 0.63909(11) 0.0472(5) Uani 1 1 d D . . . .
C1_9 C 0.4619(3) 0.67335(15) 0.68159(14) 0.0535(6) Uani 1 1 d . . . . .
H1A_9 H 0.498154 0.692441 0.723471 0.064 Uiso 1 1 calc R U . . .
H1B_9 H 0.394892 0.641444 0.698260 0.064 Uiso 1 1 calc R U . . .
C2_9 C 0.5888(3) 0.62659(15) 0.64184(16) 0.0588(7) Uani 1 1 d . . . . .
H2A_9 H 0.553544 0.607587 0.599642 0.071 Uiso 1 1 calc R U . . .
H2B_9 H 0.657535 0.657850 0.625972 0.071 Uiso 1 1 calc R U . . .
C3_9 C 0.6668(3) 0.56214(16) 0.68635(17) 0.0639(7) Uani 1 1 d . . . . .
H3A_9 H 0.596636 0.532456 0.704118 0.077 Uiso 1 1 calc R U . . .
H3B_9 H 0.739578 0.530534 0.656238 0.077 Uiso 1 1 calc R U . . .
C4_9 C 0.7397(4) 0.5846(2) 0.74719(19) 0.0787(9) Uani 1 1 d . . . . .
H4A_9 H 0.794282 0.540731 0.771051 0.118 Uiso 1 1 calc R U . . .
H4B_9 H 0.667360 0.611265 0.780041 0.118 Uiso 1 1 calc R U . . .
H4C_9 H 0.805362 0.616400 0.730411 0.118 Uiso 1 1 calc R U . . .
C5_9 C 0.3097(3) 0.71173(13) 0.57735(13) 0.0467(5) Uani 1 1 d . . . . .
H5A_9 H 0.257203 0.755167 0.551036 0.056 Uiso 1 1 calc R U . . .
H5B_9 H 0.387167 0.685862 0.545595 0.056 Uiso 1 1 calc R U . . .
C6_9 C 0.2069(3) 0.66105(14) 0.59607(14) 0.0531(6) Uani 1 1 d . . . . .
H6A_9 H 0.259690 0.615860 0.619682 0.064 Uiso 1 1 calc R U . . .
H6B_9 H 0.131038 0.685551 0.629376 0.064 Uiso 1 1 calc R U . . .
C7_9 C 0.1376(3) 0.64052(15) 0.53204(15) 0.0565(6) Uani 1 1 d . . . . .
H7A_9 H 0.213662 0.618766 0.497529 0.068 Uiso 1 1 calc R U . . .
H7B_9 H 0.080112 0.685450 0.510050 0.068 Uiso 1 1 calc R U . . .
C8_9 C 0.0412(3) 0.58623(17) 0.5499(2) 0.0735(9) Uani 1 1 d . . . . .
H8A_9 H 0.005378 0.571058 0.506608 0.110 Uiso 1 1 calc R U . . .
H8B_9 H -0.040245 0.609468 0.580016 0.110 Uiso 1 1 calc R U . . .
H8C_9 H 0.096065 0.543073 0.574609 0.110 Uiso 1 1 calc R U . . .
C13_9 C 0.2653(3) 0.78111(14) 0.68875(13) 0.0502(6) Uani 1 1 d . . . . .
H13A_9 H 0.201691 0.748179 0.707204 0.060 Uiso 1 1 calc R U . . .
H13B_9 H 0.314610 0.795375 0.729060 0.060 Uiso 1 1 calc R U . . .
C14_9 C 0.1729(3) 0.84945(14) 0.65731(14) 0.0525(6) Uani 1 1 d . . . . .
H14A_9 H 0.130396 0.836736 0.614199 0.063 Uiso 1 1 calc R U . . .
H14B_9 H 0.233844 0.885472 0.643952 0.063 Uiso 1 1 calc R U . . .
C15_9 C 0.0524(3) 0.88443(15) 0.70851(14) 0.0543(6) Uani 1 1 d . . . . .
H15A_9 H -0.010520 0.849016 0.720564 0.065 Uiso 1 1 calc R U . . .
H15B_9 H 0.094758 0.895536 0.752279 0.065 Uiso 1 1 calc R U . . .
C16_9 C -0.0372(3) 0.95446(15) 0.67792(16) 0.0597(7) Uani 1 1 d . . . . .
H16A_9 H -0.114259 0.974651 0.711795 0.090 Uiso 1 1 calc R U . . .
H16B_9 H -0.079375 0.943682 0.634563 0.090 Uiso 1 1 calc R U . . .
H16C_9 H 0.023956 0.990359 0.667617 0.090 Uiso 1 1 calc R U . . .
C9_9 C 0.4758(6) 0.7861(3) 0.6055(2) 0.048 Uiso 0.665(2) 1 d D U P B 1
H9A_9 H 0.417240 0.825116 0.576246 0.057 Uiso 0.665(2) 1 calc R U P B 1
H9B_9 H 0.547513 0.755671 0.573966 0.057 Uiso 0.665(2) 1 calc R U P B 1
C10_9 C 0.5557(4) 0.82217(19) 0.65760(17) 0.048 Uiso 0.665(2) 1 d D U P B 1
H10A_9 H 0.606228 0.784005 0.690446 0.057 Uiso 0.665(2) 1 calc R U P B 1
H10B_9 H 0.485173 0.857531 0.685372 0.057 Uiso 0.665(2) 1 calc R U P B 1
C11_9 C 0.6651(3) 0.86236(16) 0.62078(18) 0.048 Uiso 0.665(2) 1 d D U P B 1
H11A_9 H 0.722849 0.878816 0.656575 0.057 Uiso 0.665(2) 1 calc R U P B 1
H11B_9 H 0.731342 0.827690 0.590437 0.057 Uiso 0.665(2) 1 calc R U P B 1
C12_9 C 0.5945(4) 0.92897(17) 0.57606(18) 0.048 Uiso 0.665(2) 1 d D U P B 1
H12A_9 H 0.669105 0.952530 0.553793 0.071 Uiso 0.665(2) 1 calc R U P B 1
H12B_9 H 0.538887 0.912936 0.539784 0.071 Uiso 0.665(2) 1 calc R U P B 1
H12C_9 H 0.530391 0.964083 0.605949 0.071 Uiso 0.665(2) 1 calc R U P B 1
C9_91 C 0.4909(15) 0.7822(10) 0.6190(6) 0.048 Uiso 0.209(2) 1 d D U P B 2
H9A_91 H 0.443529 0.827483 0.593533 0.057 Uiso 0.209(2) 1 calc R U P B 2
H9B_91 H 0.560906 0.753433 0.585552 0.057 Uiso 0.209(2) 1 calc R U P B 2
C10_91 C 0.5749(9) 0.8047(6) 0.6783(4) 0.048 Uiso 0.209(2) 1 d D U P B 2
H10A_91 H 0.611547 0.760928 0.708439 0.057 Uiso 0.209(2) 1 calc R U P B 2
H10B_91 H 0.509274 0.840763 0.707515 0.057 Uiso 0.209(2) 1 calc R U P B 2
C11_91 C 0.7015(8) 0.8383(4) 0.6504(6) 0.048 Uiso 0.209(2) 1 d D U P B 2
H11A_91 H 0.736844 0.863210 0.688946 0.057 Uiso 0.209(2) 1 calc R U P B 2
H11B_91 H 0.667957 0.875846 0.613310 0.057 Uiso 0.209(2) 1 calc R U P B 2
C12_91 C 0.8256(9) 0.7805(5) 0.6204(6) 0.048 Uiso 0.209(2) 1 d D U P B 2
H12A_91 H 0.903961 0.804382 0.603203 0.071 Uiso 0.209(2) 1 calc R U P B 2
H12B_91 H 0.860518 0.743809 0.657158 0.071 Uiso 0.209(2) 1 calc R U P B 2
H12C_91 H 0.791643 0.756443 0.581534 0.071 Uiso 0.209(2) 1 calc R U P B 2
C9_911 C 0.465(6) 0.797(2) 0.607(3) 0.048 Uiso 0.057(2) 1 d D U P B 3
H9A_911 H 0.532563 0.763044 0.576258 0.057 Uiso 0.057(2) 1 calc R U P B 3
H9B_911 H 0.390868 0.821990 0.574409 0.057 Uiso 0.057(2) 1 calc R U P B 3
C10_911 C 0.552(3) 0.8580(12) 0.6054(16) 0.048 Uiso 0.057(2) 1 d D U P B 3
H10A_911 H 0.655792 0.835361 0.608519 0.057 Uiso 0.057(2) 1 calc R U P B 3
H10B_911 H 0.523874 0.888502 0.647000 0.057 Uiso 0.057(2) 1 calc R U P B 3
C11_911 C 0.531(4) 0.9073(11) 0.5389(13) 0.048 Uiso 0.057(2) 1 d D U P B 3
H11A_911 H 0.625488 0.908865 0.516018 0.057 Uiso 0.057(2) 1 calc R U P B 3
H11B_911 H 0.474457 0.885905 0.505769 0.057 Uiso 0.057(2) 1 calc R U P B 3
C12_911 C 0.452(4) 0.9858(12) 0.5546(19) 0.048 Uiso 0.057(2) 1 d D U P B 3
H12A_911 H 0.440416 1.015301 0.510784 0.071 Uiso 0.057(2) 1 calc R U P B 3
H12B_911 H 0.357119 0.984670 0.576425 0.071 Uiso 0.057(2) 1 calc R U P B 3
H12C_911 H 0.508132 1.007627 0.586672 0.071 Uiso 0.057(2) 1 calc R U P B 3
C9_9111 C 0.450(4) 0.8034(15) 0.6021(18) 0.048 Uiso 0.068(2) 1 d D U P B 4
H9A_9111 H 0.372414 0.845757 0.614260 0.057 Uiso 0.068(2) 1 calc R U P B 4
H9B_9111 H 0.523879 0.804308 0.636790 0.057 Uiso 0.068(2) 1 calc R U P B 4
C10_9111 C 0.519(3) 0.8389(9) 0.5394(14) 0.048 Uiso 0.068(2) 1 d D U P B 4
H10A_9111 H 0.624281 0.819102 0.538019 0.057 Uiso 0.068(2) 1 calc R U P B 4
H10B_9111 H 0.480665 0.825361 0.495558 0.057 Uiso 0.068(2) 1 calc R U P B 4
C11_9111 C 0.493(3) 0.9229(9) 0.5422(16) 0.048 Uiso 0.068(2) 1 d D U P B 4
H11A_9111 H 0.496229 0.937018 0.591442 0.057 Uiso 0.068(2) 1 calc R U P B 4
H11B_9111 H 0.395301 0.943956 0.525551 0.057 Uiso 0.068(2) 1 calc R U P B 4
C12_9111 C 0.604(3) 0.9553(13) 0.4972(16) 0.048 Uiso 0.068(2) 1 d D U P B 4
H12A_9111 H 0.582523 1.008872 0.500569 0.071 Uiso 0.068(2) 1 calc R U P B 4
H12B_9111 H 0.700203 0.935383 0.514067 0.071 Uiso 0.068(2) 1 calc R U P B 4
H12C_9111 H 0.599282 0.942321 0.448181 0.071 Uiso 0.068(2) 1 calc R U P B 4
N1_10 N 0.74835(19) 0.76135(10) 0.11294(10) 0.0424(4) Uani 1 1 d . . . . .
C1_10 C 0.7556(2) 0.69955(13) 0.06261(13) 0.0463(5) Uani 1 1 d . . . . .
H1A_10 H 0.840537 0.660750 0.073331 0.056 Uiso 1 1 calc R U . . .
H1B_10 H 0.770871 0.718760 0.014366 0.056 Uiso 1 1 calc R U . . .
C2_10 C 0.6240(3) 0.66474(13) 0.06414(15) 0.0515(6) Uani 1 1 d . . . . .
H2A_10 H 0.540655 0.701239 0.047155 0.062 Uiso 1 1 calc R U . . .
H2B_10 H 0.601126 0.650026 0.113049 0.062 Uiso 1 1 calc R U . . .
C3_10 C 0.6492(3) 0.59764(14) 0.01847(16) 0.0590(7) Uani 1 1 d . . . . .
H3A_10 H 0.728479 0.560088 0.037703 0.071 Uiso 1 1 calc R U . . .
H3B_10 H 0.561450 0.576535 0.020837 0.071 Uiso 1 1 calc R U . . .
C4_10 C 0.6860(3) 0.61419(15) -0.05710(16) 0.0618(7) Uani 1 1 d . . . . .
H4A_10 H 0.689219 0.570468 -0.084612 0.093 Uiso 1 1 calc R U . . .
H4B_10 H 0.780113 0.628217 -0.060624 0.093 Uiso 1 1 calc R U . . .
H4C_10 H 0.612725 0.654686 -0.075310 0.093 Uiso 1 1 calc R U . . .
C5_10 C 0.7520(2) 0.73263(13) 0.18858(13) 0.0465(5) Uani 1 1 d . . . . .
H5A_10 H 0.669667 0.708022 0.197714 0.056 Uiso 1 1 calc R U . . .
H5B_10 H 0.737764 0.775160 0.219559 0.056 Uiso 1 1 calc R U . . .
C6_10 C 0.8886(3) 0.67919(14) 0.20918(14) 0.0508(6) Uani 1 1 d . . . . .
H6A_10 H 0.973748 0.697044 0.189341 0.061 Uiso 1 1 calc R U . . .
H6B_10 H 0.889772 0.630461 0.189845 0.061 Uiso 1 1 calc R U . . .
C7_10 C 0.8955(3) 0.67225(16) 0.28877(14) 0.0570(6) Uani 1 1 d . . . . .
H7A_10 H 0.902226 0.720370 0.307246 0.068 Uiso 1 1 calc R U . . .
H7B_10 H 0.805358 0.659318 0.308395 0.068 Uiso 1 1 calc R U . . .
C8_10 C 1.0220(4) 0.61478(19) 0.31317(18) 0.0742(8) Uani 1 1 d . . . . .
H8A_10 H 1.023368 0.613800 0.364506 0.111 Uiso 1 1 calc R U . . .
H8B_10 H 1.111566 0.626872 0.293390 0.111 Uiso 1 1 calc R U . . .
H8C_10 H 1.012999 0.566469 0.297395 0.111 Uiso 1 1 calc R U . . .
C9_10 C 0.8783(3) 0.79536(14) 0.09338(14) 0.0484(6) Uani 1 1 d . . . . .
H9A_10 H 0.964488 0.755315 0.090101 0.058 Uiso 1 1 calc R U . . .
H9B_10 H 0.864619 0.819160 0.046178 0.058 Uiso 1 1 calc R U . . .
C10_10 C 0.9078(3) 0.85092(15) 0.14276(15) 0.0571(6) Uani 1 1 d . . . . .
H10A_10 H 0.904528 0.831016 0.191546 0.068 Uiso 1 1 calc R U . . .
H10B_10 H 0.832077 0.896017 0.139057 0.068 Uiso 1 1 calc R U . . .
C11_10 C 1.0547(3) 0.87013(16) 0.12618(15) 0.0575(6) Uani 1 1 d . . . . .
H11A_10 H 1.129376 0.824447 0.126310 0.069 Uiso 1 1 calc R U . . .
H11B_10 H 1.055268 0.893282 0.078589 0.069 Uiso 1 1 calc R U . . .
C12_10 C 1.0907(3) 0.92117(17) 0.17790(15) 0.0612(7) Uani 1 1 d . . . . .
H12A_10 H 1.186787 0.930752 0.166352 0.092 Uiso 1 1 calc R U . . .
H12B_10 H 1.088923 0.898744 0.225180 0.092 Uiso 1 1 calc R U . . .
H12C_10 H 1.019871 0.967505 0.176133 0.092 Uiso 1 1 calc R U . . .
C13_10 C 0.6086(2) 0.81753(12) 0.10781(13) 0.0457(5) Uani 1 1 d . . . . .
H13A_10 H 0.528725 0.793619 0.124391 0.055 Uiso 1 1 calc R U . . .
H13B_10 H 0.611422 0.857395 0.140268 0.055 Uiso 1 1 calc R U . . .
C14_10 C 0.5746(3) 0.85185(13) 0.03556(13) 0.0475(5) Uani 1 1 d . . . . .
H14A_10 H 0.586216 0.812915 0.000639 0.057 Uiso 1 1 calc R U . . .
H14B_10 H 0.641876 0.884630 0.021952 0.057 Uiso 1 1 calc R U . . .
C15_10 C 0.4202(3) 0.89578(13) 0.03660(14) 0.0501(6) Uani 1 1 d . . . . .
H15A_10 H 0.353854 0.862411 0.049936 0.060 Uiso 1 1 calc R U . . .
H15B_10 H 0.409002 0.933509 0.072709 0.060 Uiso 1 1 calc R U . . .
C16_10 C 0.3786(3) 0.93311(15) -0.03364(15) 0.0571(6) Uani 1 1 d . . . . .
H16A_10 H 0.278430 0.959667 -0.030500 0.086 Uiso 1 1 calc R U . . .
H16B_10 H 0.389269 0.896027 -0.069611 0.086 Uiso 1 1 calc R U . . .
H16C_10 H 0.441368 0.967772 -0.046216 0.086 Uiso 1 1 calc R U . . .


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_1 N2_1 1.380(3) . ?
N1_1 C1_3 1.407(3) . ?
N1_1 B1_1 1.558(3) . ?
C1_1 N2_1 1.282(3) . ?
C1_1 C2_1 1.464(4) . ?
C1_1 H1_1 0.9500 . ?
B1_1 C1_2 1.603(4) . ?
B1_1 C7_1 1.628(4) . ?
B1_1 C1_4 1.636(3) . ?
C2_1 C7_1 1.383(4) . ?
C2_1 C3_1 1.402(4) . ?
C3_1 C4_1 1.366(4) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.397(5) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.376(4) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.384(4) . ?
C6_1 H6_1 0.9500 . ?
N1_2 C1_2 1.150(3) . ?
C1_3 C6_3 1.394(3) . ?
C1_3 C2_3 1.414(3) . ?
C2_3 C3_3 1.388(4) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.370(4) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.375(4) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.386(3) . ?
C5_3 H5_3 0.9500 . ?
C6_3 H6_3 0.9500 . ?
C1_4 C2_4 1.397(3) . ?
C1_4 C6_4 1.399(3) . ?
C2_4 C3_4 1.394(3) . ?
C2_4 H2_4 0.9500 . ?
C3_4 C4_4 1.377(4) . ?
C3_4 H3_4 0.9500 . ?
C4_4 C5_4 1.379(4) . ?
C4_4 H4_4 0.9500 . ?
C5_4 C6_4 1.390(3) . ?
C5_4 H5_4 0.9500 . ?
C6_4 H6_4 0.9500 . ?
N1_5 N2_5 1.369(3) . ?
N1_5 C1_6 1.410(3) . ?
N1_5 B1_5 1.558(4) . ?
C1_5 N2_5 1.307(4) . ?
C1_5 C2_5 1.440(4) . ?
C1_5 H1_5 0.9500 . ?
B1_5 C1_7 1.626(4) . ?
B1_5 C7_5 1.626(4) . ?
B1_5 C1_8 1.631(4) . ?
C2_5 C7_5 1.398(4) . ?
C2_5 C3_5 1.412(4) . ?
C3_5 C4_5 1.378(5) . ?
C3_5 H3_5 0.9500 . ?
C4_5 C5_5 1.367(5) . ?
C4_5 H4_5 0.9500 . ?
C5_5 C6_5 1.390(4) . ?
C5_5 H5_5 0.9500 . ?
C6_5 C7_5 1.384(4) . ?
C6_5 H6_5 0.9500 . ?
B1_51 N1_51 1.5097 . ?
B1_51 C7_51 1.5906 . ?
B1_51 C1_8 1.699(10) . ?
B1_51 C1_7 1.829(10) . ?
N1_51 C1_61 1.409(3) . ?
N1_51 N2_51 1.4561 . ?
N2_51 C1_51 1.3208 . ?
C1_51 C2_51 1.4727 . ?
C1_51 H1_51 0.9500 . ?
C2_51 C7_51 1.3924 . ?
C2_51 C3_51 1.4202 . ?
C3_51 C4_51 1.2702 . ?
C3_51 H3_51 0.9500 . ?
C4_51 C5_51 1.4578 . ?
C4_51 H4_51 0.9500 . ?
C5_51 C6_51 1.3784 . ?
C5_51 H5_51 0.9500 . ?
C6_51 C7_51 1.3926 . ?
C6_51 H6_51 0.9500 . ?
C1_6 C6_6 1.395(4) . ?
C1_6 C2_6 1.403(4) . ?
C2_6 C3_6 1.392(4) . ?
C2_6 H2_6 0.9500 . ?
C3_6 C4_6 1.405(5) . ?
C3_6 H3_6 0.9500 . ?
C4_6 C5_6 1.372(4) . ?
C4_6 H4_6 0.9500 . ?
C5_6 C6_6 1.385(4) . ?
C5_6 H5_6 0.9500 . ?
C6_6 H6_6 0.9500 . ?
C1_61 C2_61 1.3900 . ?
C1_61 C6_61 1.3900 . ?
C2_61 C3_61 1.3900 . ?
C2_61 H2_61 0.9500 . ?
C3_61 C4_61 1.3900 . ?
C3_61 H3_61 0.9500 . ?
C4_61 C5_61 1.3900 . ?
C4_61 H4_61 0.9500 . ?
C5_61 C6_61 1.3900 . ?
C5_61 H5_61 0.9500 . ?
C6_61 H6_61 0.9500 . ?
C1_7 C6_7 1.392(3) . ?
C1_7 C2_7 1.399(3) . ?
C2_7 C3_7 1.384(3) . ?
C2_7 H2_7 0.9500 . ?
C3_7 C4_7 1.380(4) . ?
C3_7 H3_7 0.9500 . ?
C4_7 C5_7 1.384(4) . ?
C4_7 H4_7 0.9500 . ?
C5_7 C6_7 1.378(4) . ?
C5_7 H5_7 0.9500 . ?
C6_7 H6_7 0.9500 . ?
N1_8 C1_8 1.160(3) . ?
N1_9 C9_91 1.504(9) . ?
N1_9 C5_9 1.516(3) . ?
N1_9 C9_9 1.519(4) . ?
N1_9 C13_9 1.520(3) . ?
N1_9 C1_9 1.527(3) . ?
N1_9 C9_911 1.592(14) . ?
N1_9 C9_9111 1.632(13) . ?
C1_9 C2_9 1.527(4) . ?
C1_9 H1A_9 0.9900 . ?
C1_9 H1B_9 0.9900 . ?
C2_9 C3_9 1.524(4) . ?
C2_9 H2A_9 0.9900 . ?
C2_9 H2B_9 0.9900 . ?
C3_9 C4_9 1.493(4) . ?
C3_9 H3A_9 0.9900 . ?
C3_9 H3B_9 0.9900 . ?
C4_9 H4A_9 0.9800 . ?
C4_9 H4B_9 0.9800 . ?
C4_9 H4C_9 0.9800 . ?
C5_9 C6_9 1.513(3) . ?
C5_9 H5A_9 0.9900 . ?
C5_9 H5B_9 0.9900 . ?
C6_9 C7_9 1.511(4) . ?
C6_9 H6A_9 0.9900 . ?
C6_9 H6B_9 0.9900 . ?
C7_9 C8_9 1.516(4) . ?
C7_9 H7A_9 0.9900 . ?
C7_9 H7B_9 0.9900 . ?
C8_9 H8A_9 0.9800 . ?
C8_9 H8B_9 0.9800 . ?
C8_9 H8C_9 0.9800 . ?
C13_9 C14_9 1.510(4) . ?
C13_9 H13A_9 0.9900 . ?
C13_9 H13B_9 0.9900 . ?
C14_9 C15_9 1.530(3) . ?
C14_9 H14A_9 0.9900 . ?
C14_9 H14B_9 0.9900 . ?
C15_9 C16_9 1.515(4) . ?
C15_9 H15A_9 0.9900 . ?
C15_9 H15B_9 0.9900 . ?
C16_9 H16A_9 0.9800 . ?
C16_9 H16B_9 0.9800 . ?
C16_9 H16C_9 0.9800 . ?
C9_9 C10_9 1.531(2) . ?
C9_9 H9A_9 0.9900 . ?
C9_9 H9B_9 0.9900 . ?
C10_9 C11_9 1.5307(19) . ?
C10_9 H10A_9 0.9900 . ?
C10_9 H10B_9 0.9900 . ?
C11_9 C12_9 1.5303(19) . ?
C11_9 H11A_9 0.9900 . ?
C11_9 H11B_9 0.9900 . ?
C12_9 H12A_9 0.9800 . ?
C12_9 H12B_9 0.9800 . ?
C12_9 H12C_9 0.9800 . ?
C9_91 C10_91 1.532(2) . ?
C9_91 H9A_91 0.9900 . ?
C9_91 H9B_91 0.9900 . ?
C10_91 C11_91 1.532(2) . ?
C10_91 H10A_91 0.9900 . ?
C10_91 H10B_91 0.9900 . ?
C11_91 C12_91 1.532(2) . ?
C11_91 H11A_91 0.9900 . ?
C11_91 H11B_91 0.9900 . ?
C12_91 H12A_91 0.9800 . ?
C12_91 H12B_91 0.9800 . ?
C12_91 H12C_91 0.9800 . ?
C9_911 C10_911 1.533(2) . ?
C9_911 H9A_911 0.9900 . ?
C9_911 H9B_911 0.9900 . ?
C10_911 C11_911 1.533(2) . ?
C10_911 H10A_911 0.9900 . ?
C10_911 H10B_911 0.9900 . ?
C11_911 C12_911 1.533(2) . ?
C11_911 H11A_911 0.9900 . ?
C11_911 H11B_911 0.9900 . ?
C12_911 H12A_911 0.9800 . ?
C12_911 H12B_911 0.9800 . ?
C12_911 H12C_911 0.9800 . ?
C9_9111 C10_9111 1.533(2) . ?
C9_9111 H9A_9111 0.9900 . ?
C9_9111 H9B_9111 0.9900 . ?
C10_9111 C11_9111 1.533(2) . ?
C10_9111 H10A_9111 0.9900 . ?
C10_9111 H10B_9111 0.9900 . ?
C11_9111 C12_9111 1.533(2) . ?
C11_9111 H11A_9111 0.9900 . ?
C11_9111 H11B_9111 0.9900 . ?
C12_9111 H12A_9111 0.9800 . ?
C12_9111 H12B_9111 0.9800 . ?
C12_9111 H12C_9111 0.9800 . ?
N1_10 C1_10 1.516(3) . ?
N1_10 C13_10 1.518(3) . ?
N1_10 C5_10 1.519(3) . ?
N1_10 C9_10 1.525(3) . ?
C1_10 C2_10 1.519(3) . ?
C1_10 H1A_10 0.9900 . ?
C1_10 H1B_10 0.9900 . ?
C2_10 C3_10 1.523(4) . ?
C2_10 H2A_10 0.9900 . ?
C2_10 H2B_10 0.9900 . ?
C3_10 C4_10 1.504(4) . ?
C3_10 H3A_10 0.9900 . ?
C3_10 H3B_10 0.9900 . ?
C4_10 H4A_10 0.9800 . ?
C4_10 H4B_10 0.9800 . ?
C4_10 H4C_10 0.9800 . ?
C5_10 C6_10 1.522(3) . ?
C5_10 H5A_10 0.9900 . ?
C5_10 H5B_10 0.9900 . ?
C6_10 C7_10 1.523(4) . ?
C6_10 H6A_10 0.9900 . ?
C6_10 H6B_10 0.9900 . ?
C7_10 C8_10 1.514(4) . ?
C7_10 H7A_10 0.9900 . ?
C7_10 H7B_10 0.9900 . ?
C8_10 H8A_10 0.9800 . ?
C8_10 H8B_10 0.9800 . ?
C8_10 H8C_10 0.9800 . ?
C9_10 C10_10 1.501(4) . ?
C9_10 H9A_10 0.9900 . ?
C9_10 H9B_10 0.9900 . ?
C10_10 C11_10 1.528(3) . ?
C10_10 H10A_10 0.9900 . ?
C10_10 H10B_10 0.9900 . ?
C11_10 C12_10 1.493(4) . ?
C11_10 H11A_10 0.9900 . ?
C11_10 H11B_10 0.9900 . ?
C12_10 H12A_10 0.9800 . ?
C12_10 H12B_10 0.9800 . ?
C12_10 H12C_10 0.9800 . ?
C13_10 C14_10 1.517(4) . ?
C13_10 H13A_10 0.9900 . ?
C13_10 H13B_10 0.9900 . ?
C14_10 C15_10 1.527(3) . ?
C14_10 H14A_10 0.9900 . ?
C14_10 H14B_10 0.9900 . ?
C15_10 C16_10 1.516(4) . ?
C15_10 H15A_10 0.9900 . ?
C15_10 H15B_10 0.9900 . ?
C16_10 H16A_10 0.9800 . ?
C16_10 H16B_10 0.9800 . ?
C16_10 H16C_10 0.9800 . ?

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
N2_1 N1_1 C1_3 112.36(18) . . ?
N2_1 N1_1 B1_1 123.49(19) . . ?
C1_3 N1_1 B1_1 123.56(19) . . ?
N2_1 C1_1 C2_1 127.0(2) . . ?
N2_1 C1_1 H1_1 116.5 . . ?
C2_1 C1_1 H1_1 116.5 . . ?
N1_1 B1_1 C1_2 110.05(19) . . ?
N1_1 B1_1 C7_1 107.56(19) . . ?
C1_2 B1_1 C7_1 106.4(2) . . ?
N1_1 B1_1 C1_4 112.4(2) . . ?
C1_2 B1_1 C1_4 108.82(19) . . ?
C7_1 B1_1 C1_4 111.39(19) . . ?
C1_1 N2_1 N1_1 119.3(2) . . ?
C7_1 C2_1 C3_1 121.5(3) . . ?
C7_1 C2_1 C1_1 118.0(2) . . ?
C3_1 C2_1 C1_1 120.4(3) . . ?
C4_1 C3_1 C2_1 120.1(3) . . ?
C4_1 C3_1 H3_1 120.0 . . ?
C2_1 C3_1 H3_1 120.0 . . ?
C3_1 C4_1 C5_1 119.6(3) . . ?
C3_1 C4_1 H4_1 120.2 . . ?
C5_1 C4_1 H4_1 120.2 . . ?
C6_1 C5_1 C4_1 119.1(3) . . ?
C6_1 C5_1 H5_1 120.4 . . ?
C4_1 C5_1 H5_1 120.4 . . ?
C5_1 C6_1 C7_1 122.9(3) . . ?
C5_1 C6_1 H6_1 118.5 . . ?
C7_1 C6_1 H6_1 118.5 . . ?
C2_1 C7_1 C6_1 116.8(2) . . ?
C2_1 C7_1 B1_1 120.1(2) . . ?
C6_1 C7_1 B1_1 123.1(2) . . ?
N1_2 C1_2 B1_1 174.1(2) . . ?
C6_3 C1_3 N1_1 121.2(2) . . ?
C6_3 C1_3 C2_3 117.7(2) . . ?
N1_1 C1_3 C2_3 121.0(2) . . ?
C3_3 C2_3 C1_3 119.7(2) . . ?
C3_3 C2_3 H2_3 120.1 . . ?
C1_3 C2_3 H2_3 120.1 . . ?
C4_3 C3_3 C2_3 121.7(2) . . ?
C4_3 C3_3 H3_3 119.1 . . ?
C2_3 C3_3 H3_3 119.1 . . ?
C3_3 C4_3 C5_3 118.8(2) . . ?
C3_3 C4_3 H4_3 120.6 . . ?
C5_3 C4_3 H4_3 120.6 . . ?
C4_3 C5_3 C6_3 121.1(2) . . ?
C4_3 C5_3 H5_3 119.5 . . ?
C6_3 C5_3 H5_3 119.5 . . ?
C5_3 C6_3 C1_3 120.9(2) . . ?
C5_3 C6_3 H6_3 119.5 . . ?
C1_3 C6_3 H6_3 119.5 . . ?
C2_4 C1_4 C6_4 116.2(2) . . ?
C2_4 C1_4 B1_1 121.9(2) . . ?
C6_4 C1_4 B1_1 121.9(2) . . ?
C3_4 C2_4 C1_4 122.2(2) . . ?
C3_4 C2_4 H2_4 118.9 . . ?
C1_4 C2_4 H2_4 118.9 . . ?
C4_4 C3_4 C2_4 120.0(2) . . ?
C4_4 C3_4 H3_4 120.0 . . ?
C2_4 C3_4 H3_4 120.0 . . ?
C3_4 C4_4 C5_4 119.4(2) . . ?
C3_4 C4_4 H4_4 120.3 . . ?
C5_4 C4_4 H4_4 120.3 . . ?
C4_4 C5_4 C6_4 120.3(3) . . ?
C4_4 C5_4 H5_4 119.8 . . ?
C6_4 C5_4 H5_4 119.8 . . ?
C5_4 C6_4 C1_4 121.9(2) . . ?
C5_4 C6_4 H6_4 119.0 . . ?
C1_4 C6_4 H6_4 119.0 . . ?
N2_5 N1_5 C1_6 112.0(2) . . ?
N2_5 N1_5 B1_5 123.7(2) . . ?
C1_6 N1_5 B1_5 123.0(2) . . ?
N2_5 C1_5 C2_5 127.5(3) . . ?
N2_5 C1_5 H1_5 116.3 . . ?
C2_5 C1_5 H1_5 116.3 . . ?
N1_5 B1_5 C1_7 110.3(2) . . ?
N1_5 B1_5 C7_5 109.1(2) . . ?
C1_7 B1_5 C7_5 111.0(2) . . ?
N1_5 B1_5 C1_8 109.0(2) . . ?
C1_7 B1_5 C1_8 110.0(2) . . ?
C7_5 B1_5 C1_8 107.4(2) . . ?
C1_5 N2_5 N1_5 119.3(3) . . ?
C7_5 C2_5 C3_5 120.4(3) . . ?
C7_5 C2_5 C1_5 118.5(3) . . ?
C3_5 C2_5 C1_5 121.0(3) . . ?
C4_5 C3_5 C2_5 119.8(3) . . ?
C4_5 C3_5 H3_5 120.1 . . ?
C2_5 C3_5 H3_5 120.1 . . ?
C5_5 C4_5 C3_5 120.1(3) . . ?
C5_5 C4_5 H4_5 119.9 . . ?
C3_5 C4_5 H4_5 119.9 . . ?
C4_5 C5_5 C6_5 120.3(3) . . ?
C4_5 C5_5 H5_5 119.9 . . ?
C6_5 C5_5 H5_5 119.9 . . ?
C7_5 C6_5 C5_5 121.6(3) . . ?
C7_5 C6_5 H6_5 119.2 . . ?
C5_5 C6_5 H6_5 119.2 . . ?
C6_5 C7_5 C2_5 117.8(3) . . ?
C6_5 C7_5 B1_5 123.2(2) . . ?
C2_5 C7_5 B1_5 118.9(3) . . ?
N1_51 B1_51 C7_51 111.4 . . ?
N1_51 B1_51 C1_8 105.9(5) . . ?
C7_51 B1_51 C1_8 121.9(6) . . ?
N1_51 B1_51 C1_7 100.3(5) . . ?
C7_51 B1_51 C1_7 116.3(5) . . ?
C1_8 B1_51 C1_7 98.2(4) . . ?
C1_61 N1_51 N2_51 105.5(11) . . ?
C1_61 N1_51 B1_51 128.4(11) . . ?
N2_51 N1_51 B1_51 125.3 . . ?
C1_51 N2_51 N1_51 114.7 . . ?
N2_51 C1_51 C2_51 128.2 . . ?
N2_51 C1_51 H1_51 115.9 . . ?
C2_51 C1_51 H1_51 115.9 . . ?
C7_51 C2_51 C3_51 122.3 . . ?
C7_51 C2_51 C1_51 118.8 . . ?
C3_51 C2_51 C1_51 118.8 . . ?
C4_51 C3_51 C2_51 120.1 . . ?
C4_51 C3_51 H3_51 120.0 . . ?
C2_51 C3_51 H3_51 120.0 . . ?
C3_51 C4_51 C5_51 120.9 . . ?
C3_51 C4_51 H4_51 119.6 . . ?
C5_51 C4_51 H4_51 119.6 . . ?
C6_51 C5_51 C4_51 118.9 . . ?
C6_51 C5_51 H5_51 120.6 . . ?
C4_51 C5_51 H5_51 120.6 . . ?
C5_51 C6_51 C7_51 121.0 . . ?
C5_51 C6_51 H6_51 119.5 . . ?
C7_51 C6_51 H6_51 119.5 . . ?
C2_51 C7_51 C6_51 116.7 . . ?
C2_51 C7_51 B1_51 119.8 . . ?
C6_51 C7_51 B1_51 123.4 . . ?
C6_6 C1_6 C2_6 117.8(2) . . ?
C6_6 C1_6 N1_5 120.7(2) . . ?
C2_6 C1_6 N1_5 121.4(2) . . ?
C3_6 C2_6 C1_6 120.1(3) . . ?
C3_6 C2_6 H2_6 119.9 . . ?
C1_6 C2_6 H2_6 119.9 . . ?
C2_6 C3_6 C4_6 121.5(3) . . ?
C2_6 C3_6 H3_6 119.3 . . ?
C4_6 C3_6 H3_6 119.3 . . ?
C5_6 C4_6 C3_6 117.6(3) . . ?
C5_6 C4_6 H4_6 121.2 . . ?
C3_6 C4_6 H4_6 121.2 . . ?
C4_6 C5_6 C6_6 121.7(3) . . ?
C4_6 C5_6 H5_6 119.1 . . ?
C6_6 C5_6 H5_6 119.1 . . ?
C5_6 C6_6 C1_6 121.2(3) . . ?
C5_6 C6_6 H6_6 119.4 . . ?
C1_6 C6_6 H6_6 119.4 . . ?
C2_61 C1_61 C6_61 120.0 . . ?
C2_61 C1_61 N1_51 120.3(14) . . ?
C6_61 C1_61 N1_51 119.7(14) . . ?
C1_61 C2_61 C3_61 120.0 . . ?
C1_61 C2_61 H2_61 120.0 . . ?
C3_61 C2_61 H2_61 120.0 . . ?
C2_61 C3_61 C4_61 120.0 . . ?
C2_61 C3_61 H3_61 120.0 . . ?
C4_61 C3_61 H3_61 120.0 . . ?
C3_61 C4_61 C5_61 120.0 . . ?
C3_61 C4_61 H4_61 120.0 . . ?
C5_61 C4_61 H4_61 120.0 . . ?
C6_61 C5_61 C4_61 120.0 . . ?
C6_61 C5_61 H5_61 120.0 . . ?
C4_61 C5_61 H5_61 120.0 . . ?
C5_61 C6_61 C1_61 120.0 . . ?
C5_61 C6_61 H6_61 120.0 . . ?
C1_61 C6_61 H6_61 120.0 . . ?
C6_7 C1_7 C2_7 116.5(2) . . ?
C6_7 C1_7 B1_5 121.7(2) . . ?
C2_7 C1_7 B1_5 121.5(2) . . ?
C6_7 C1_7 B1_51 130.5(4) . . ?
C2_7 C1_7 B1_51 107.0(3) . . ?
C3_7 C2_7 C1_7 121.9(2) . . ?
C3_7 C2_7 H2_7 119.1 . . ?
C1_7 C2_7 H2_7 119.1 . . ?
C4_7 C3_7 C2_7 119.8(2) . . ?
C4_7 C3_7 H3_7 120.1 . . ?
C2_7 C3_7 H3_7 120.1 . . ?
C3_7 C4_7 C5_7 119.8(2) . . ?
C3_7 C4_7 H4_7 120.1 . . ?
C5_7 C4_7 H4_7 120.1 . . ?
C6_7 C5_7 C4_7 119.7(2) . . ?
C6_7 C5_7 H5_7 120.2 . . ?
C4_7 C5_7 H5_7 120.2 . . ?
C5_7 C6_7 C1_7 122.4(2) . . ?
C5_7 C6_7 H6_7 118.8 . . ?
C1_7 C6_7 H6_7 118.8 . . ?
N1_8 C1_8 B1_5 173.1(3) . . ?
N1_8 C1_8 B1_51 153.7(4) . . ?
C9_91 N1_9 C5_9 114.3(4) . . ?
C5_9 N1_9 C9_9 104.0(2) . . ?
C9_91 N1_9 C13_9 110.0(7) . . ?
C5_9 N1_9 C13_9 111.32(19) . . ?
C9_9 N1_9 C13_9 111.7(3) . . ?
C9_91 N1_9 C1_9 102.8(6) . . ?
C5_9 N1_9 C1_9 110.90(18) . . ?
C9_9 N1_9 C1_9 112.0(3) . . ?
C13_9 N1_9 C1_9 107.03(19) . . ?
C5_9 N1_9 C9_911 105(2) . . ?
C13_9 N1_9 C9_911 105(2) . . ?
C1_9 N1_9 C9_911 117(2) . . ?
C5_9 N1_9 C9_9111 101.5(15) . . ?
C13_9 N1_9 C9_9111 101.6(14) . . ?
C1_9 N1_9 C9_9111 124.0(16) . . ?
C2_9 C1_9 N1_9 114.8(2) . . ?
C2_9 C1_9 H1A_9 108.6 . . ?
N1_9 C1_9 H1A_9 108.6 . . ?
C2_9 C1_9 H1B_9 108.6 . . ?
N1_9 C1_9 H1B_9 108.6 . . ?
H1A_9 C1_9 H1B_9 107.5 . . ?
C3_9 C2_9 C1_9 112.6(2) . . ?
C3_9 C2_9 H2A_9 109.1 . . ?
C1_9 C2_9 H2A_9 109.1 . . ?
C3_9 C2_9 H2B_9 109.1 . . ?
C1_9 C2_9 H2B_9 109.1 . . ?
H2A_9 C2_9 H2B_9 107.8 . . ?
C4_9 C3_9 C2_9 113.8(3) . . ?
C4_9 C3_9 H3A_9 108.8 . . ?
C2_9 C3_9 H3A_9 108.8 . . ?
C4_9 C3_9 H3B_9 108.8 . . ?
C2_9 C3_9 H3B_9 108.8 . . ?
H3A_9 C3_9 H3B_9 107.7 . . ?
C3_9 C4_9 H4A_9 109.5 . . ?
C3_9 C4_9 H4B_9 109.5 . . ?
H4A_9 C4_9 H4B_9 109.5 . . ?
C3_9 C4_9 H4C_9 109.5 . . ?
H4A_9 C4_9 H4C_9 109.5 . . ?
H4B_9 C4_9 H4C_9 109.5 . . ?
C6_9 C5_9 N1_9 115.2(2) . . ?
C6_9 C5_9 H5A_9 108.5 . . ?
N1_9 C5_9 H5A_9 108.5 . . ?
C6_9 C5_9 H5B_9 108.5 . . ?
N1_9 C5_9 H5B_9 108.5 . . ?
H5A_9 C5_9 H5B_9 107.5 . . ?
C7_9 C6_9 C5_9 111.9(2) . . ?
C7_9 C6_9 H6A_9 109.2 . . ?
C5_9 C6_9 H6A_9 109.2 . . ?
C7_9 C6_9 H6B_9 109.2 . . ?
C5_9 C6_9 H6B_9 109.2 . . ?
H6A_9 C6_9 H6B_9 107.9 . . ?
C6_9 C7_9 C8_9 112.1(3) . . ?
C6_9 C7_9 H7A_9 109.2 . . ?
C8_9 C7_9 H7A_9 109.2 . . ?
C6_9 C7_9 H7B_9 109.2 . . ?
C8_9 C7_9 H7B_9 109.2 . . ?
H7A_9 C7_9 H7B_9 107.9 . . ?
C7_9 C8_9 H8A_9 109.5 . . ?
C7_9 C8_9 H8B_9 109.5 . . ?
H8A_9 C8_9 H8B_9 109.5 . . ?
C7_9 C8_9 H8C_9 109.5 . . ?
H8A_9 C8_9 H8C_9 109.5 . . ?
H8B_9 C8_9 H8C_9 109.5 . . ?
C14_9 C13_9 N1_9 115.5(2) . . ?
C14_9 C13_9 H13A_9 108.4 . . ?
N1_9 C13_9 H13A_9 108.4 . . ?
C14_9 C13_9 H13B_9 108.4 . . ?
N1_9 C13_9 H13B_9 108.4 . . ?
H13A_9 C13_9 H13B_9 107.5 . . ?
C13_9 C14_9 C15_9 111.9(2) . . ?
C13_9 C14_9 H14A_9 109.2 . . ?
C15_9 C14_9 H14A_9 109.2 . . ?
C13_9 C14_9 H14B_9 109.2 . . ?
C15_9 C14_9 H14B_9 109.2 . . ?
H14A_9 C14_9 H14B_9 107.9 . . ?
C16_9 C15_9 C14_9 111.9(2) . . ?
C16_9 C15_9 H15A_9 109.2 . . ?
C14_9 C15_9 H15A_9 109.2 . . ?
C16_9 C15_9 H15B_9 109.2 . . ?
C14_9 C15_9 H15B_9 109.2 . . ?
H15A_9 C15_9 H15B_9 107.9 . . ?
C15_9 C16_9 H16A_9 109.5 . . ?
C15_9 C16_9 H16B_9 109.5 . . ?
H16A_9 C16_9 H16B_9 109.5 . . ?
C15_9 C16_9 H16C_9 109.5 . . ?
H16A_9 C16_9 H16C_9 109.5 . . ?
H16B_9 C16_9 H16C_9 109.5 . . ?
N1_9 C9_9 C10_9 114.6(3) . . ?
N1_9 C9_9 H9A_9 108.6 . . ?
C10_9 C9_9 H9A_9 108.6 . . ?
N1_9 C9_9 H9B_9 108.6 . . ?
C10_9 C9_9 H9B_9 108.6 . . ?
H9A_9 C9_9 H9B_9 107.6 . . ?
C9_9 C10_9 C11_9 112.1(2) . . ?
C9_9 C10_9 H10A_9 109.2 . . ?
C11_9 C10_9 H10A_9 109.2 . . ?
C9_9 C10_9 H10B_9 109.2 . . ?
C11_9 C10_9 H10B_9 109.2 . . ?
H10A_9 C10_9 H10B_9 107.9 . . ?
C12_9 C11_9 C10_9 112.9(2) . . ?
C12_9 C11_9 H11A_9 109.0 . . ?
C10_9 C11_9 H11A_9 109.0 . . ?
C12_9 C11_9 H11B_9 109.0 . . ?
C10_9 C11_9 H11B_9 109.0 . . ?
H11A_9 C11_9 H11B_9 107.8 . . ?
C11_9 C12_9 H12A_9 109.5 . . ?
C11_9 C12_9 H12B_9 109.5 . . ?
H12A_9 C12_9 H12B_9 109.5 . . ?
C11_9 C12_9 H12C_9 109.5 . . ?
H12A_9 C12_9 H12C_9 109.5 . . ?
H12B_9 C12_9 H12C_9 109.5 . . ?
N1_9 C9_91 C10_91 117.3(7) . . ?
N1_9 C9_91 H9A_91 108.0 . . ?
C10_91 C9_91 H9A_91 108.0 . . ?
N1_9 C9_91 H9B_91 108.0 . . ?
C10_91 C9_91 H9B_91 108.0 . . ?
H9A_91 C9_91 H9B_91 107.2 . . ?
C9_91 C10_91 C11_91 112.1(4) . . ?
C9_91 C10_91 H10A_91 109.2 . . ?
C11_91 C10_91 H10A_91 109.2 . . ?
C9_91 C10_91 H10B_91 109.2 . . ?
C11_91 C10_91 H10B_91 109.2 . . ?
H10A_91 C10_91 H10B_91 107.9 . . ?
C10_91 C11_91 C12_91 112.2(4) . . ?
C10_91 C11_91 H11A_91 109.2 . . ?
C12_91 C11_91 H11A_91 109.2 . . ?
C10_91 C11_91 H11B_91 109.2 . . ?
C12_91 C11_91 H11B_91 109.2 . . ?
H11A_91 C11_91 H11B_91 107.9 . . ?
C11_91 C12_91 H12A_91 109.5 . . ?
C11_91 C12_91 H12B_91 109.5 . . ?
H12A_91 C12_91 H12B_91 109.5 . . ?
C11_91 C12_91 H12C_91 109.5 . . ?
H12A_91 C12_91 H12C_91 109.5 . . ?
H12B_91 C12_91 H12C_91 109.5 . . ?
C10_911 C9_911 N1_9 158(4) . . ?
C10_911 C9_911 H9A_911 96.7 . . ?
N1_9 C9_911 H9A_911 96.7 . . ?
C10_911 C9_911 H9B_911 96.7 . . ?
N1_9 C9_911 H9B_911 96.7 . . ?
H9A_911 C9_911 H9B_911 103.5 . . ?
C9_911 C10_911 C11_911 112.7(4) . . ?
C9_911 C10_911 H10A_911 109.1 . . ?
C11_911 C10_911 H10A_911 109.1 . . ?
C9_911 C10_911 H10B_911 109.1 . . ?
C11_911 C10_911 H10B_911 109.1 . . ?
H10A_911 C10_911 H10B_911 107.8 . . ?
C12_911 C11_911 C10_911 112.3(4) . . ?
C12_911 C11_911 H11A_911 109.1 . . ?
C10_911 C11_911 H11A_911 109.1 . . ?
C12_911 C11_911 H11B_911 109.1 . . ?
C10_911 C11_911 H11B_911 109.1 . . ?
H11A_911 C11_911 H11B_911 107.9 . . ?
C11_911 C12_911 H12A_911 109.5 . . ?
C11_911 C12_911 H12B_911 109.5 . . ?
H12A_911 C12_911 H12B_911 109.5 . . ?
C11_911 C12_911 H12C_911 109.5 . . ?
H12A_911 C12_911 H12C_911 109.5 . . ?
H12B_911 C12_911 H12C_911 109.5 . . ?
C10_9111 C9_9111 N1_9 153(2) . . ?
C10_9111 C9_9111 H9A_9111 98.4 . . ?
N1_9 C9_9111 H9A_9111 98.4 . . ?
C10_9111 C9_9111 H9B_9111 98.4 . . ?
N1_9 C9_9111 H9B_9111 98.4 . . ?
H9A_9111 C9_9111 H9B_9111 103.8 . . ?
C11_9111 C10_9111 C9_9111 113.0(4) . . ?
C11_9111 C10_9111 H10A_9111 109.0 . . ?
C9_9111 C10_9111 H10A_9111 109.0 . . ?
C11_9111 C10_9111 H10B_9111 109.0 . . ?
C9_9111 C10_9111 H10B_9111 109.0 . . ?
H10A_9111 C10_9111 H10B_9111 107.8 . . ?
C10_9111 C11_9111 C12_9111 112.3(4) . . ?
C10_9111 C11_9111 H11A_9111 109.1 . . ?
C12_9111 C11_9111 H11A_9111 109.1 . . ?
C10_9111 C11_9111 H11B_9111 109.1 . . ?
C12_9111 C11_9111 H11B_9111 109.1 . . ?
H11A_9111 C11_9111 H11B_9111 107.9 . . ?
C11_9111 C12_9111 H12A_9111 109.5 . . ?
C11_9111 C12_9111 H12B_9111 109.5 . . ?
H12A_9111 C12_9111 H12B_9111 109.5 . . ?
C11_9111 C12_9111 H12C_9111 109.5 . . ?
H12A_9111 C12_9111 H12C_9111 109.5 . . ?
H12B_9111 C12_9111 H12C_9111 109.5 . . ?
C1_10 N1_10 C13_10 111.75(18) . . ?
C1_10 N1_10 C5_10 111.09(17) . . ?
C13_10 N1_10 C5_10 105.54(17) . . ?
C1_10 N1_10 C9_10 105.66(17) . . ?
C13_10 N1_10 C9_10 111.60(17) . . ?
C5_10 N1_10 C9_10 111.32(18) . . ?
N1_10 C1_10 C2_10 115.45(19) . . ?
N1_10 C1_10 H1A_10 108.4 . . ?
C2_10 C1_10 H1A_10 108.4 . . ?
N1_10 C1_10 H1B_10 108.4 . . ?
C2_10 C1_10 H1B_10 108.4 . . ?
H1A_10 C1_10 H1B_10 107.5 . . ?
C1_10 C2_10 C3_10 111.2(2) . . ?
C1_10 C2_10 H2A_10 109.4 . . ?
C3_10 C2_10 H2A_10 109.4 . . ?
C1_10 C2_10 H2B_10 109.4 . . ?
C3_10 C2_10 H2B_10 109.4 . . ?
H2A_10 C2_10 H2B_10 108.0 . . ?
C4_10 C3_10 C2_10 113.5(2) . . ?
C4_10 C3_10 H3A_10 108.9 . . ?
C2_10 C3_10 H3A_10 108.9 . . ?
C4_10 C3_10 H3B_10 108.9 . . ?
C2_10 C3_10 H3B_10 108.9 . . ?
H3A_10 C3_10 H3B_10 107.7 . . ?
C3_10 C4_10 H4A_10 109.5 . . ?
C3_10 C4_10 H4B_10 109.5 . . ?
H4A_10 C4_10 H4B_10 109.5 . . ?
C3_10 C4_10 H4C_10 109.5 . . ?
H4A_10 C4_10 H4C_10 109.5 . . ?
H4B_10 C4_10 H4C_10 109.5 . . ?
N1_10 C5_10 C6_10 116.01(18) . . ?
N1_10 C5_10 H5A_10 108.3 . . ?
C6_10 C5_10 H5A_10 108.3 . . ?
N1_10 C5_10 H5B_10 108.3 . . ?
C6_10 C5_10 H5B_10 108.3 . . ?
H5A_10 C5_10 H5B_10 107.4 . . ?
C5_10 C6_10 C7_10 109.9(2) . . ?
C5_10 C6_10 H6A_10 109.7 . . ?
C7_10 C6_10 H6A_10 109.7 . . ?
C5_10 C6_10 H6B_10 109.7 . . ?
C7_10 C6_10 H6B_10 109.7 . . ?
H6A_10 C6_10 H6B_10 108.2 . . ?
C8_10 C7_10 C6_10 112.8(2) . . ?
C8_10 C7_10 H7A_10 109.0 . . ?
C6_10 C7_10 H7A_10 109.0 . . ?
C8_10 C7_10 H7B_10 109.0 . . ?
C6_10 C7_10 H7B_10 109.0 . . ?
H7A_10 C7_10 H7B_10 107.8 . . ?
C7_10 C8_10 H8A_10 109.5 . . ?
C7_10 C8_10 H8B_10 109.5 . . ?
H8A_10 C8_10 H8B_10 109.5 . . ?
C7_10 C8_10 H8C_10 109.5 . . ?
H8A_10 C8_10 H8C_10 109.5 . . ?
H8B_10 C8_10 H8C_10 109.5 . . ?
C10_10 C9_10 N1_10 115.9(2) . . ?
C10_10 C9_10 H9A_10 108.3 . . ?
N1_10 C9_10 H9A_10 108.3 . . ?
C10_10 C9_10 H9B_10 108.3 . . ?
N1_10 C9_10 H9B_10 108.3 . . ?
H9A_10 C9_10 H9B_10 107.4 . . ?
C9_10 C10_10 C11_10 111.2(2) . . ?
C9_10 C10_10 H10A_10 109.4 . . ?
C11_10 C10_10 H10A_10 109.4 . . ?
C9_10 C10_10 H10B_10 109.4 . . ?
C11_10 C10_10 H10B_10 109.4 . . ?
H10A_10 C10_10 H10B_10 108.0 . . ?
C12_10 C11_10 C10_10 112.1(2) . . ?
C12_10 C11_10 H11A_10 109.2 . . ?
C10_10 C11_10 H11A_10 109.2 . . ?
C12_10 C11_10 H11B_10 109.2 . . ?
C10_10 C11_10 H11B_10 109.2 . . ?
H11A_10 C11_10 H11B_10 107.9 . . ?
C11_10 C12_10 H12A_10 109.5 . . ?
C11_10 C12_10 H12B_10 109.5 . . ?
H12A_10 C12_10 H12B_10 109.5 . . ?
C11_10 C12_10 H12C_10 109.5 . . ?
H12A_10 C12_10 H12C_10 109.5 . . ?
H12B_10 C12_10 H12C_10 109.5 . . ?
C14_10 C13_10 N1_10 116.13(18) . . ?
C14_10 C13_10 H13A_10 108.3 . . ?
N1_10 C13_10 H13A_10 108.3 . . ?
C14_10 C13_10 H13B_10 108.3 . . ?
N1_10 C13_10 H13B_10 108.3 . . ?
H13A_10 C13_10 H13B_10 107.4 . . ?
C13_10 C14_10 C15_10 109.42(19) . . ?
C13_10 C14_10 H14A_10 109.8 . . ?
C15_10 C14_10 H14A_10 109.8 . . ?
C13_10 C14_10 H14B_10 109.8 . . ?
C15_10 C14_10 H14B_10 109.8 . . ?
H14A_10 C14_10 H14B_10 108.2 . . ?
C16_10 C15_10 C14_10 112.6(2) . . ?
C16_10 C15_10 H15A_10 109.1 . . ?
C14_10 C15_10 H15A_10 109.1 . . ?
C16_10 C15_10 H15B_10 109.1 . . ?
C14_10 C15_10 H15B_10 109.1 . . ?
H15A_10 C15_10 H15B_10 107.8 . . ?
C15_10 C16_10 H16A_10 109.5 . . ?
C15_10 C16_10 H16B_10 109.5 . . ?
H16A_10 C16_10 H16B_10 109.5 . . ?
C15_10 C16_10 H16C_10 109.5 . . ?
H16A_10 C16_10 H16C_10 109.5 . . ?
H16B_10 C16_10 H16C_10 109.5 . . ?

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
N2_1 N1_1 B1_1 C1_2 -140.0(2) . . . . ?
C1_3 N1_1 B1_1 C1_2 49.5(3) . . . . ?
N2_1 N1_1 B1_1 C7_1 -24.4(3) . . . . ?
C1_3 N1_1 B1_1 C7_1 165.0(2) . . . . ?
N2_1 N1_1 B1_1 C1_4 98.5(3) . . . . ?
C1_3 N1_1 B1_1 C1_4 -72.0(3) . . . . ?
C2_1 C1_1 N2_1 N1_1 4.0(4) . . . . ?
C1_3 N1_1 N2_1 C1_1 -173.6(2) . . . . ?
B1_1 N1_1 N2_1 C1_1 15.0(3) . . . . ?
N2_1 C1_1 C2_1 C7_1 -9.1(4) . . . . ?
N2_1 C1_1 C2_1 C3_1 166.9(3) . . . . ?
C7_1 C2_1 C3_1 C4_1 -1.1(4) . . . . ?
C1_1 C2_1 C3_1 C4_1 -176.9(3) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.3(4) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.7(4) . . . . ?
C4_1 C5_1 C6_1 C7_1 -1.0(4) . . . . ?
C3_1 C2_1 C7_1 C6_1 0.8(4) . . . . ?
C1_1 C2_1 C7_1 C6_1 176.7(2) . . . . ?
C3_1 C2_1 C7_1 B1_1 179.8(2) . . . . ?
C1_1 C2_1 C7_1 B1_1 -4.3(3) . . . . ?
C5_1 C6_1 C7_1 C2_1 0.3(4) . . . . ?
C5_1 C6_1 C7_1 B1_1 -178.7(2) . . . . ?
N1_1 B1_1 C7_1 C2_1 18.4(3) . . . . ?
C1_2 B1_1 C7_1 C2_1 136.3(2) . . . . ?
C1_4 B1_1 C7_1 C2_1 -105.2(2) . . . . ?
N1_1 B1_1 C7_1 C6_1 -162.7(2) . . . . ?
C1_2 B1_1 C7_1 C6_1 -44.8(3) . . . . ?
C1_4 B1_1 C7_1 C6_1 73.7(3) . . . . ?
N2_1 N1_1 C1_3 C6_3 -160.6(2) . . . . ?
B1_1 N1_1 C1_3 C6_3 10.8(3) . . . . ?
N2_1 N1_1 C1_3 C2_3 21.4(3) . . . . ?
B1_1 N1_1 C1_3 C2_3 -167.2(2) . . . . ?
C6_3 C1_3 C2_3 C3_3 0.9(4) . . . . ?
N1_1 C1_3 C2_3 C3_3 179.0(2) . . . . ?
C1_3 C2_3 C3_3 C4_3 -0.7(4) . . . . ?
C2_3 C3_3 C4_3 C5_3 0.4(4) . . . . ?
C3_3 C4_3 C5_3 C6_3 -0.4(4) . . . . ?
C4_3 C5_3 C6_3 C1_3 0.7(4) . . . . ?
N1_1 C1_3 C6_3 C5_3 -179.0(2) . . . . ?
C2_3 C1_3 C6_3 C5_3 -0.9(4) . . . . ?
N1_1 B1_1 C1_4 C2_4 162.7(2) . . . . ?
C1_2 B1_1 C1_4 C2_4 40.6(3) . . . . ?
C7_1 B1_1 C1_4 C2_4 -76.5(3) . . . . ?
N1_1 B1_1 C1_4 C6_4 -20.8(3) . . . . ?
C1_2 B1_1 C1_4 C6_4 -142.9(2) . . . . ?
C7_1 B1_1 C1_4 C6_4 100.0(3) . . . . ?
C6_4 C1_4 C2_4 C3_4 -0.6(4) . . . . ?
B1_1 C1_4 C2_4 C3_4 176.1(2) . . . . ?
C1_4 C2_4 C3_4 C4_4 0.1(4) . . . . ?
C2_4 C3_4 C4_4 C5_4 0.5(4) . . . . ?
C3_4 C4_4 C5_4 C6_4 -0.6(4) . . . . ?
C4_4 C5_4 C6_4 C1_4 0.0(4) . . . . ?
C2_4 C1_4 C6_4 C5_4 0.5(3) . . . . ?
B1_1 C1_4 C6_4 C5_4 -176.1(2) . . . . ?
N2_5 N1_5 B1_5 C1_7 103.8(3) . . . . ?
C1_6 N1_5 B1_5 C1_7 -62.1(3) . . . . ?
N2_5 N1_5 B1_5 C7_5 -18.3(3) . . . . ?
C1_6 N1_5 B1_5 C7_5 175.7(2) . . . . ?
N2_5 N1_5 B1_5 C1_8 -135.3(2) . . . . ?
C1_6 N1_5 B1_5 C1_8 58.8(3) . . . . ?
C2_5 C1_5 N2_5 N1_5 4.9(5) . . . . ?
C1_6 N1_5 N2_5 C1_5 175.2(3) . . . . ?
B1_5 N1_5 N2_5 C1_5 7.9(4) . . . . ?
N2_5 C1_5 C2_5 C7_5 -3.7(5) . . . . ?
N2_5 C1_5 C2_5 C3_5 172.4(3) . . . . ?
C7_5 C2_5 C3_5 C4_5 1.3(4) . . . . ?
C1_5 C2_5 C3_5 C4_5 -174.7(3) . . . . ?
C2_5 C3_5 C4_5 C5_5 0.8(4) . . . . ?
C3_5 C4_5 C5_5 C6_5 -1.9(5) . . . . ?
C4_5 C5_5 C6_5 C7_5 0.9(5) . . . . ?
C5_5 C6_5 C7_5 C2_5 1.2(4) . . . . ?
C5_5 C6_5 C7_5 B1_5 -175.4(3) . . . . ?
C3_5 C2_5 C7_5 C6_5 -2.3(4) . . . . ?
C1_5 C2_5 C7_5 C6_5 173.9(3) . . . . ?
C3_5 C2_5 C7_5 B1_5 174.5(3) . . . . ?
C1_5 C2_5 C7_5 B1_5 -9.3(4) . . . . ?
N1_5 B1_5 C7_5 C6_5 -164.9(2) . . . . ?
C1_7 B1_5 C7_5 C6_5 73.3(3) . . . . ?
C1_8 B1_5 C7_5 C6_5 -47.0(3) . . . . ?
N1_5 B1_5 C7_5 C2_5 18.5(3) . . . . ?
C1_7 B1_5 C7_5 C2_5 -103.3(3) . . . . ?
C1_8 B1_5 C7_5 C2_5 136.4(2) . . . . ?
C7_51 B1_51 N1_51 C1_61 176.4(12) . . . . ?
C1_8 B1_51 N1_51 C1_61 -49.0(11) . . . . ?
C1_7 B1_51 N1_51 C1_61 52.7(11) . . . . ?
C7_51 B1_51 N1_51 N2_51 -15.0 . . . . ?
C1_8 B1_51 N1_51 N2_51 119.6(7) . . . . ?
C1_7 B1_51 N1_51 N2_51 -138.7(6) . . . . ?
C1_61 N1_51 N2_51 C1_51 -174.1(10) . . . . ?
B1_51 N1_51 N2_51 C1_51 15.2 . . . . ?
N1_51 N2_51 C1_51 C2_51 -8.8 . . . . ?
N2_51 C1_51 C2_51 C7_51 3.8 . . . . ?
N2_51 C1_51 C2_51 C3_51 -174.1 . . . . ?
C7_51 C2_51 C3_51 C4_51 2.1 . . . . ?
C1_51 C2_51 C3_51 C4_51 179.9 . . . . ?
C2_51 C3_51 C4_51 C5_51 1.1 . . . . ?
C3_51 C4_51 C5_51 C6_51 -3.0 . . . . ?
C4_51 C5_51 C6_51 C7_51 1.7 . . . . ?
C3_51 C2_51 C7_51 C6_51 -3.2 . . . . ?
C1_51 C2_51 C7_51 C6_51 178.9 . . . . ?
C3_51 C2_51 C7_51 B1_51 174.1 . . . . ?
C1_51 C2_51 C7_51 B1_51 -3.8 . . . . ?
C5_51 C6_51 C7_51 C2_51 1.2 . . . . ?
C5_51 C6_51 C7_51 B1_51 -176.0 . . . . ?
N1_51 B1_51 C7_51 C2_51 8.8 . . . . ?
C1_8 B1_51 C7_51 C2_51 -117.4(7) . . . . ?
C1_7 B1_51 C7_51 C2_51 122.9(6) . . . . ?
N1_51 B1_51 C7_51 C6_51 -174.0 . . . . ?
C1_8 B1_51 C7_51 C6_51 59.7(7) . . . . ?
C1_7 B1_51 C7_51 C6_51 -60.0(6) . . . . ?
N2_5 N1_5 C1_6 C6_6 -167.6(2) . . . . ?
B1_5 N1_5 C1_6 C6_6 -0.2(4) . . . . ?
N2_5 N1_5 C1_6 C2_6 12.4(3) . . . . ?
B1_5 N1_5 C1_6 C2_6 179.8(2) . . . . ?
C6_6 C1_6 C2_6 C3_6 1.0(4) . . . . ?
N1_5 C1_6 C2_6 C3_6 -179.0(2) . . . . ?
C1_6 C2_6 C3_6 C4_6 0.5(4) . . . . ?
C2_6 C3_6 C4_6 C5_6 -1.3(4) . . . . ?
C3_6 C4_6 C5_6 C6_6 0.6(4) . . . . ?
C4_6 C5_6 C6_6 C1_6 0.8(4) . . . . ?
C2_6 C1_6 C6_6 C5_6 -1.6(4) . . . . ?
N1_5 C1_6 C6_6 C5_6 178.3(2) . . . . ?
N2_51 N1_51 C1_61 C2_61 -151.7(9) . . . . ?
B1_51 N1_51 C1_61 C2_61 18.6(15) . . . . ?
N2_51 N1_51 C1_61 C6_61 29.6(13) . . . . ?
B1_51 N1_51 C1_61 C6_61 -160.1(9) . . . . ?
C6_61 C1_61 C2_61 C3_61 0.0 . . . . ?
N1_51 C1_61 C2_61 C3_61 -178.7(16) . . . . ?
C1_61 C2_61 C3_61 C4_61 0.0 . . . . ?
C2_61 C3_61 C4_61 C5_61 0.0 . . . . ?
C3_61 C4_61 C5_61 C6_61 0.0 . . . . ?
C4_61 C5_61 C6_61 C1_61 0.0 . . . . ?
C2_61 C1_61 C6_61 C5_61 0.0 . . . . ?
N1_51 C1_61 C6_61 C5_61 178.7(16) . . . . ?
N1_5 B1_5 C1_7 C6_7 161.6(2) . . . . ?
C7_5 B1_5 C1_7 C6_7 -77.3(3) . . . . ?
C1_8 B1_5 C1_7 C6_7 41.4(3) . . . . ?
N1_5 B1_5 C1_7 C2_7 -24.4(3) . . . . ?
C7_5 B1_5 C1_7 C2_7 96.7(3) . . . . ?
C1_8 B1_5 C1_7 C2_7 -144.6(2) . . . . ?
N1_51 B1_51 C1_7 C6_7 -131.2(3) . . . . ?
C7_51 B1_51 C1_7 C6_7 108.5(4) . . . . ?
C1_8 B1_51 C1_7 C6_7 -23.4(7) . . . . ?
N1_51 B1_51 C1_7 C2_7 77.7(4) . . . . ?
C7_51 B1_51 C1_7 C2_7 -42.5(5) . . . . ?
C1_8 B1_51 C1_7 C2_7 -174.4(3) . . . . ?
C6_7 C1_7 C2_7 C3_7 -0.6(3) . . . . ?
B1_5 C1_7 C2_7 C3_7 -174.9(2) . . . . ?
B1_51 C1_7 C2_7 C3_7 155.1(4) . . . . ?
C1_7 C2_7 C3_7 C4_7 -0.4(3) . . . . ?
C2_7 C3_7 C4_7 C5_7 1.0(3) . . . . ?
C3_7 C4_7 C5_7 C6_7 -0.7(4) . . . . ?
C4_7 C5_7 C6_7 C1_7 -0.3(4) . . . . ?
C2_7 C1_7 C6_7 C5_7 0.9(3) . . . . ?
B1_5 C1_7 C6_7 C5_7 175.2(2) . . . . ?
B1_51 C1_7 C6_7 C5_7 -147.9(5) . . . . ?
N1_51 B1_51 C1_8 N1_8 -128.1(9) . . . . ?
C7_51 B1_51 C1_8 N1_8 0.5(12) . . . . ?
C1_7 B1_51 C1_8 N1_8 128.7(7) . . . . ?
C9_91 N1_9 C1_9 C2_9 -59.6(6) . . . . ?
C5_9 N1_9 C1_9 C2_9 62.9(3) . . . . ?
C9_9 N1_9 C1_9 C2_9 -52.8(3) . . . . ?
C13_9 N1_9 C1_9 C2_9 -175.5(2) . . . . ?
C9_911 N1_9 C1_9 C2_9 -58(2) . . . . ?
C9_9111 N1_9 C1_9 C2_9 -58.1(16) . . . . ?
N1_9 C1_9 C2_9 C3_9 -179.1(2) . . . . ?
C1_9 C2_9 C3_9 C4_9 -65.6(3) . . . . ?
C9_91 N1_9 C5_9 C6_9 174.2(8) . . . . ?
C9_9 N1_9 C5_9 C6_9 179.2(3) . . . . ?
C13_9 N1_9 C5_9 C6_9 -60.5(3) . . . . ?
C1_9 N1_9 C5_9 C6_9 58.6(3) . . . . ?
C9_911 N1_9 C5_9 C6_9 -173(2) . . . . ?
C9_9111 N1_9 C5_9 C6_9 -167.9(15) . . . . ?
N1_9 C5_9 C6_9 C7_9 177.0(2) . . . . ?
C5_9 C6_9 C7_9 C8_9 176.6(2) . . . . ?
C9_91 N1_9 C13_9 C14_9 67.2(6) . . . . ?
C5_9 N1_9 C13_9 C14_9 -60.5(3) . . . . ?
C9_9 N1_9 C13_9 C14_9 55.2(3) . . . . ?
C1_9 N1_9 C13_9 C14_9 178.2(2) . . . . ?
C9_911 N1_9 C13_9 C14_9 53(2) . . . . ?
C9_9111 N1_9 C13_9 C14_9 46.9(16) . . . . ?
N1_9 C13_9 C14_9 C15_9 173.8(2) . . . . ?
C13_9 C14_9 C15_9 C16_9 178.0(2) . . . . ?
C5_9 N1_9 C9_9 C10_9 178.2(4) . . . . ?
C13_9 N1_9 C9_9 C10_9 58.0(5) . . . . ?
C1_9 N1_9 C9_9 C10_9 -62.0(5) . . . . ?
N1_9 C9_9 C10_9 C11_9 173.4(4) . . . . ?
C9_9 C10_9 C11_9 C12_9 66.4(5) . . . . ?
C5_9 N1_9 C9_91 C10_91 -174.4(10) . . . . ?
C13_9 N1_9 C9_91 C10_91 59.5(14) . . . . ?
C1_9 N1_9 C9_91 C10_91 -54.2(14) . . . . ?
N1_9 C9_91 C10_91 C11_91 170.9(10) . . . . ?
C9_91 C10_91 C11_91 C12_91 -73.1(13) . . . . ?
C5_9 N1_9 C9_911 C10_911 170(11) . . . . ?
C13_9 N1_9 C9_911 C10_911 53(12) . . . . ?
C1_9 N1_9 C9_911 C10_911 -66(12) . . . . ?
N1_9 C9_911 C10_911 C11_911 -151(11) . . . . ?
C9_911 C10_911 C11_911 C12_911 113(4) . . . . ?
C5_9 N1_9 C9_9111 C10_9111 -30(7) . . . . ?
C13_9 N1_9 C9_9111 C10_9111 -145(7) . . . . ?
C1_9 N1_9 C9_9111 C10_9111 95(7) . . . . ?
N1_9 C9_9111 C10_9111 C11_9111 152(6) . . . . ?
C9_9111 C10_9111 C11_9111 C12_9111 159(3) . . . . ?
C13_10 N1_10 C1_10 C2_10 -49.2(3) . . . . ?
C5_10 N1_10 C1_10 C2_10 68.4(3) . . . . ?
C9_10 N1_10 C1_10 C2_10 -170.7(2) . . . . ?
N1_10 C1_10 C2_10 C3_10 -173.1(2) . . . . ?
C1_10 C2_10 C3_10 C4_10 -58.6(3) . . . . ?
C1_10 N1_10 C5_10 C6_10 63.4(2) . . . . ?
C13_10 N1_10 C5_10 C6_10 -175.32(19) . . . . ?
C9_10 N1_10 C5_10 C6_10 -54.1(3) . . . . ?
N1_10 C5_10 C6_10 C7_10 164.0(2) . . . . ?
C5_10 C6_10 C7_10 C8_10 174.9(2) . . . . ?
C1_10 N1_10 C9_10 C10_10 -171.2(2) . . . . ?
C13_10 N1_10 C9_10 C10_10 67.1(3) . . . . ?
C5_10 N1_10 C9_10 C10_10 -50.5(3) . . . . ?
N1_10 C9_10 C10_10 C11_10 169.0(2) . . . . ?
C9_10 C10_10 C11_10 C12_10 -175.8(2) . . . . ?
C1_10 N1_10 C13_10 C14_10 -55.8(2) . . . . ?
C5_10 N1_10 C13_10 C14_10 -176.70(19) . . . . ?
C9_10 N1_10 C13_10 C14_10 62.2(3) . . . . ?
N1_10 C13_10 C14_10 C15_10 169.74(18) . . . . ?
C13_10 C14_10 C15_10 C16_10 178.9(2) . . . . ?


