# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_6Thio
_database_code_depnum_ccdc_archive 'CCDC 2541879'
loop_
_audit_author_name
_audit_author_address
'Andreas Haefner'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2026-03-28 deposited with the CCDC.	2026-06-03 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.6l (K.Radacki, 2005-26)'
_audit_creation_date             2026-02-04
_shelx_SHELXL_version_number     2025/1
_chemical_formula_moiety         'C11 H8 B2 N2 O2 S'
_chemical_formula_sum            'C11 H8 B2 N2 O2 S'
_chemical_formula_weight         253.87
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'
S S 0.3331 0.5567 '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        'I 2/a'
_space_group_name_Hall           '-I 2ya'
_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'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'


_cell_length_a                   16.396(4)
_cell_length_b                   5.0103(8)
_cell_length_c                   27.778(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.702(8)
_cell_angle_gamma                90
_cell_volume                     2277.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4978
_cell_measurement_theta_min      3.1480
_cell_measurement_theta_max      74.4390
_cell_special_details            
;
 Uncertainties of the unit cell parameters were calculated as standard 
 deviations on 50 cells obtained from subsets of all reflections. These sets 
 of reflections were based on runs in experiment.
;

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.460
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.44.111a (Rigaku Oxford Diffraction, 2025) 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 0.1852
1 -1 -1 0.1855
-1 1 1 0.1579
-1 1 -1 0.1585
0 -1 1 0.1920
0 -1 -1 0.1908
1 1 0 0.1626
1 1 -1 0.1639
0 0 1 0.0236
0 0 -1 0.0274
-1 0 1 0.0438
1 0 -1 0.0268
-1 0 0 0.0388
1 0 0 0.0231

_shelx_estimated_absorpt_T_min   0.471
_shelx_estimated_absorpt_T_max   0.887
_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     55.00  91.00   0.50    0.05    --   42.00  51.00-154.04   72
  2  ω     30.00  60.00   0.50    0.05    --   18.00  55.00 -74.66   60
  3  ω     29.00  56.00   0.50    0.05    --   18.00  60.00 -14.18   54
  4  ω     36.00  71.00   0.50    0.05    --   22.00  50.00 122.40   70
  5  ω     29.00  56.00   0.50    0.05    --   18.00  60.00 168.55   54
  6  ω    -98.00 -22.00   0.50    0.05    --  -69.91 126.00   0.00  152
  7  ω    -34.00  -8.00   0.50    0.05    --  -10.00 117.00-120.77   52
  8  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00 -20.95   70
  9  ω   -126.00 -91.00   0.50    0.05    --  -79.50 -58.00 -82.93   70
 10  ω   -121.00 -86.00   0.50    0.05    --  -74.00 -58.00-113.27   70
 11  ω   -118.00 -83.00   0.50    0.05    --  -70.00 -53.00 -83.95   70
 12  ω   -127.00 -92.00   0.50    0.05    --  -79.50 -55.00 -14.88   70
 13  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00-103.50   70
 14  ω    -89.00 -50.00   0.50    0.05    --  -38.00 -41.00 -12.19   78
 15  ω   -123.00 -87.00   0.50    0.05    --  -74.00 -51.00 -64.30   72
 16  ω   -117.00 -83.00   0.50    0.05    --  -70.00 -56.00  40.16   68
 17  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00 169.90   70
 18  ω   -127.00 -91.00   0.50    0.05    --  -79.50 -56.00 167.63   72
 19  ω   -116.00 -79.00   0.50    0.05    --  -66.00 -47.00 166.25   74
 20  ω   -106.00 -71.00   0.50    0.05    --  -58.00 -52.00  84.75   70
 21  ω   -125.00 -86.00   0.50    0.05    --  -74.00 -41.00 -14.20   78
 22  ω   -112.00 -43.00   0.50    0.05    --  -60.42 -18.00  -6.00  138
 23  ω   -107.00 -72.00   0.50    0.05    --  -58.00 -48.00 -62.43   70
 24  ω   -121.00 -52.00   0.50    0.05    --  -69.91 -18.00  -6.00  138
 25  ω   -128.00 -59.00   0.50    0.05    --  -76.44 -18.00  -6.00  138
 26  ω   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00-125.78   70
 27  ω   -115.00 -80.00   0.50    0.05    --  -66.00 -49.00-150.94   70
 28  ω   -128.00 -59.00   0.50    0.05    --  -76.44 -18.00  -6.00  138
 29  ω     29.00  93.00   0.50    0.05    --   77.00-112.00  30.00  128
 30  ω     34.00  85.00   0.50    0.05    --   77.00 -95.00  30.00  102
 31  ω     16.00  67.00   0.50    0.05    --   58.82 -95.00   0.00  102
 32  ω     29.00  79.00   0.50    0.05    --   71.51 -95.00 -60.00  100
 33  ω     34.00  85.00   0.50    0.05    --   77.00 -95.00-120.00  102
 34  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00-180.00  100
 35  ω     34.00  85.00   0.50    0.05    --   77.00 -95.00-180.00  102
 36  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00 -90.00  100
 37  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00   0.00  100
 38  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00 -60.00  100
 39  ω     34.00  85.00   0.50    0.05    --   77.00 -95.00  90.00  102
 40  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00 120.00  100
 41  ω     29.00  79.00   0.50    0.05    --   71.51 -95.00 150.00  100
 42  ω     16.00  67.00   0.50    0.05    --   58.82 -95.00 150.00  102
 43  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00  60.00  100
 44  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00 -30.00  100
 45  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00-120.00  100
 46  ω     42.00  92.00   0.50    0.05    --   84.80 -95.00-150.00  100
 47  ω     41.00 110.00   0.50    0.05    --   58.82  18.00 162.00  138
 48  ω     53.00 123.00   0.50    0.05    --   71.51  18.00 162.00  140
 49  ω     59.00 128.00   0.50    0.05    --   77.00  18.00 162.00  138
 50  ω     67.00 136.00   0.50    0.05    --   84.80  18.00 162.00  138
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0433832000
_diffrn_orient_matrix_UB_12      0.2718002000
_diffrn_orient_matrix_UB_13      0.0026081000
_diffrn_orient_matrix_UB_21      0.0828257000
_diffrn_orient_matrix_UB_22      0.1364513000
_diffrn_orient_matrix_UB_23      0.0125470000
_diffrn_orient_matrix_UB_31      0.0108700000
_diffrn_orient_matrix_UB_32      0.0446359000
_diffrn_orient_matrix_UB_33      -0.0541120000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            20337
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_max         75.246
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2266
_reflns_number_gt                1655
_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 44.111a 64-bit (release 13-05-2025))
;
_computing_cell_refinement       'CrysAlisPro 1.171.44.111a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.111a (Rigaku OD, 2025)'
_computing_structure_solution    "SHELXT 2014/5 (Sheldrick, 2014)'"
_computing_structure_refinement  'SHELXL-2025/1 (Sheldrick, 2025)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2025/1 (Sheldrick, 2025)'

_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)+(0.1310P)²+0.6527P] 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         2266
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2138
_refine_ls_wR_factor_gt          0.1870
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.095
_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
S1_1 S 0.65153(6) -0.18639(19) 0.71949(3) 0.0347(3) Uani 1 1 d . . . . .
O1_1 O 0.49736(15) 0.1272(5) 0.56130(9) 0.0316(6) Uani 1 1 d . . . . .
O2_1 O 0.42594(19) 0.2701(6) 0.48827(10) 0.0443(8) Uani 1 1 d . . . . .
H2A_1 H 0.452(3) 0.148(9) 0.4785(7) 0.067 Uiso 1 1 calc R U . . .
N1_1 N 0.46946(17) 0.3346(5) 0.63828(10) 0.0272(7) Uani 1 1 d . . . . .
N2_1 N 0.47893(18) 0.3658(6) 0.68754(11) 0.0307(7) Uani 1 1 d . . . . .
C1_1 C 0.4109(2) 0.5152(7) 0.61607(13) 0.0300(8) Uani 1 1 d . . . . .
C2_1 C 0.3702(2) 0.7022(7) 0.64296(14) 0.0297(8) Uani 1 1 d . . . . .
H2_1 H 0.380840 0.711987 0.676944 0.036 Uiso 1 1 calc R U . . .
C3_1 C 0.3137(2) 0.8750(7) 0.61962(15) 0.0342(9) Uani 1 1 d . . . . .
H3_1 H 0.286360 1.003899 0.637786 0.041 Uiso 1 1 calc R U . . .
C4_1 C 0.2974(2) 0.8598(7) 0.57024(15) 0.0374(9) Uani 1 1 d . . . . .
H4_1 H 0.257964 0.975121 0.554686 0.045 Uiso 1 1 calc R U . . .
C5_1 C 0.3384(2) 0.6771(7) 0.54354(14) 0.0350(9) Uani 1 1 d . . . . .
H5_1 H 0.327954 0.671309 0.509523 0.042 Uiso 1 1 calc R U . . .
C6_1 C 0.3956(2) 0.4994(7) 0.56587(13) 0.0321(8) Uani 1 1 d . . . . .
C7_1 C 0.5325(2) 0.2136(7) 0.71085(14) 0.0328(8) Uani 1 1 d . . . . .
H7_1 H 0.540404 0.236536 0.744779 0.039 Uiso 1 1 calc R U . . .
C8_1 C 0.5800(2) 0.0159(7) 0.68898(13) 0.0311(8) Uani 1 1 d . . . . .
C9_1 C 0.5729(2) -0.0357(7) 0.63957(13) 0.0295(8) Uani 1 1 d . . . . .
C10_1 C 0.6264(2) -0.2478(7) 0.62778(14) 0.0318(8) Uani 1 1 d . . . . .
H10_1 H 0.630243 -0.314777 0.596013 0.038 Uiso 1 1 calc R U . . .
C11_1 C 0.6712(2) -0.3435(7) 0.66697(14) 0.0319(8) Uani 1 1 d . . . . .
H11_1 H 0.709699 -0.484311 0.665266 0.038 Uiso 1 1 calc R U . . .
B1_1 B 0.5121(2) 0.1428(8) 0.61112(16) 0.0304(9) Uani 1 1 d . . . . .
B2_1 B 0.4408(3) 0.2930(9) 0.53669(16) 0.0347(10) Uani 1 1 d . . . . .


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
S1_1 C11_1 1.707(4) . ?
S1_1 C8_1 1.730(4) . ?
O1_1 B2_1 1.391(5) . ?
O1_1 B1_1 1.391(5) . ?
O2_1 B2_1 1.356(5) . ?
O2_1 H2A_1 0.80(5) . ?
N1_1 N2_1 1.376(4) . ?
N1_1 C1_1 1.430(4) . ?
N1_1 B1_1 1.431(5) . ?
N2_1 C7_1 1.304(4) . ?
C1_1 C2_1 1.395(5) . ?
C1_1 C6_1 1.403(5) . ?
C2_1 C3_1 1.396(5) . ?
C2_1 H2_1 0.9500 . ?
C3_1 C4_1 1.383(6) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.380(5) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.407(5) . ?
C5_1 H5_1 0.9500 . ?
C6_1 B2_1 1.535(6) . ?
C7_1 C8_1 1.420(5) . ?
C7_1 H7_1 0.9500 . ?
C8_1 C9_1 1.394(5) . ?
C9_1 C10_1 1.429(5) . ?
C9_1 B1_1 1.523(5) . ?
C10_1 C11_1 1.360(5) . ?
C10_1 H10_1 0.9500 . ?
C11_1 H11_1 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
C11_1 S1_1 C8_1 90.62(17) . . ?
B2_1 O1_1 B1_1 121.5(3) . . ?
B2_1 O2_1 H2A_1 109.5 . . ?
N2_1 N1_1 C1_1 112.7(3) . . ?
N2_1 N1_1 B1_1 125.0(3) . . ?
C1_1 N1_1 B1_1 122.3(3) . . ?
C7_1 N2_1 N1_1 117.2(3) . . ?
C2_1 C1_1 C6_1 120.6(3) . . ?
C2_1 C1_1 N1_1 121.7(3) . . ?
C6_1 C1_1 N1_1 117.7(3) . . ?
C1_1 C2_1 C3_1 119.6(3) . . ?
C1_1 C2_1 H2_1 120.2 . . ?
C3_1 C2_1 H2_1 120.2 . . ?
C4_1 C3_1 C2_1 120.5(3) . . ?
C4_1 C3_1 H3_1 119.8 . . ?
C2_1 C3_1 H3_1 119.8 . . ?
C5_1 C4_1 C3_1 120.0(3) . . ?
C5_1 C4_1 H4_1 120.0 . . ?
C3_1 C4_1 H4_1 120.0 . . ?
C4_1 C5_1 C6_1 121.1(4) . . ?
C4_1 C5_1 H5_1 119.4 . . ?
C6_1 C5_1 H5_1 119.4 . . ?
C1_1 C6_1 C5_1 118.3(3) . . ?
C1_1 C6_1 B2_1 120.1(3) . . ?
C5_1 C6_1 B2_1 121.6(3) . . ?
N2_1 C7_1 C8_1 124.5(3) . . ?
N2_1 C7_1 H7_1 117.8 . . ?
C8_1 C7_1 H7_1 117.8 . . ?
C9_1 C8_1 C7_1 122.5(3) . . ?
C9_1 C8_1 S1_1 112.6(3) . . ?
C7_1 C8_1 S1_1 124.9(3) . . ?
C8_1 C9_1 C10_1 110.5(3) . . ?
C8_1 C9_1 B1_1 114.4(3) . . ?
C10_1 C9_1 B1_1 135.1(3) . . ?
C11_1 C10_1 C9_1 112.7(3) . . ?
C11_1 C10_1 H10_1 123.6 . . ?
C9_1 C10_1 H10_1 123.6 . . ?
C10_1 C11_1 S1_1 113.5(3) . . ?
C10_1 C11_1 H11_1 123.2 . . ?
S1_1 C11_1 H11_1 123.2 . . ?
O1_1 B1_1 N1_1 120.2(3) . . ?
O1_1 B1_1 C9_1 123.3(3) . . ?
N1_1 B1_1 C9_1 116.5(3) . . ?
O2_1 B2_1 O1_1 120.6(4) . . ?
O2_1 B2_1 C6_1 121.2(3) . . ?
O1_1 B2_1 C6_1 118.2(3) . . ?

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_1 N1_1 N2_1 C7_1 -178.5(3) . . . . ?
B1_1 N1_1 N2_1 C7_1 2.0(5) . . . . ?
N2_1 N1_1 C1_1 C2_1 0.9(5) . . . . ?
B1_1 N1_1 C1_1 C2_1 -179.6(3) . . . . ?
N2_1 N1_1 C1_1 C6_1 -179.3(3) . . . . ?
B1_1 N1_1 C1_1 C6_1 0.2(5) . . . . ?
C6_1 C1_1 C2_1 C3_1 0.0(5) . . . . ?
N1_1 C1_1 C2_1 C3_1 179.8(3) . . . . ?
C1_1 C2_1 C3_1 C4_1 0.7(5) . . . . ?
C2_1 C3_1 C4_1 C5_1 -1.5(6) . . . . ?
C3_1 C4_1 C5_1 C6_1 1.7(6) . . . . ?
C2_1 C1_1 C6_1 C5_1 0.1(5) . . . . ?
N1_1 C1_1 C6_1 C5_1 -179.6(3) . . . . ?
C2_1 C1_1 C6_1 B2_1 179.9(3) . . . . ?
N1_1 C1_1 C6_1 B2_1 0.2(5) . . . . ?
C4_1 C5_1 C6_1 C1_1 -1.0(6) . . . . ?
C4_1 C5_1 C6_1 B2_1 179.2(4) . . . . ?
N1_1 N2_1 C7_1 C8_1 -1.4(5) . . . . ?
N2_1 C7_1 C8_1 C9_1 -0.5(6) . . . . ?
N2_1 C7_1 C8_1 S1_1 179.8(3) . . . . ?
C11_1 S1_1 C8_1 C9_1 -0.9(3) . . . . ?
C11_1 S1_1 C8_1 C7_1 178.9(3) . . . . ?
C7_1 C8_1 C9_1 C10_1 -178.7(3) . . . . ?
S1_1 C8_1 C9_1 C10_1 1.1(4) . . . . ?
C7_1 C8_1 C9_1 B1_1 1.7(5) . . . . ?
S1_1 C8_1 C9_1 B1_1 -178.6(2) . . . . ?
C8_1 C9_1 C10_1 C11_1 -0.8(4) . . . . ?
B1_1 C9_1 C10_1 C11_1 178.8(4) . . . . ?
C9_1 C10_1 C11_1 S1_1 0.2(4) . . . . ?
C8_1 S1_1 C11_1 C10_1 0.4(3) . . . . ?
B2_1 O1_1 B1_1 N1_1 -0.8(5) . . . . ?
B2_1 O1_1 B1_1 C9_1 179.6(3) . . . . ?
N2_1 N1_1 B1_1 O1_1 179.6(3) . . . . ?
C1_1 N1_1 B1_1 O1_1 0.1(5) . . . . ?
N2_1 N1_1 B1_1 C9_1 -0.8(5) . . . . ?
C1_1 N1_1 B1_1 C9_1 179.8(3) . . . . ?
C8_1 C9_1 B1_1 O1_1 178.6(3) . . . . ?
C10_1 C9_1 B1_1 O1_1 -1.0(6) . . . . ?
C8_1 C9_1 B1_1 N1_1 -1.0(5) . . . . ?
C10_1 C9_1 B1_1 N1_1 179.4(3) . . . . ?
B1_1 O1_1 B2_1 O2_1 -178.4(4) . . . . ?
B1_1 O1_1 B2_1 C6_1 1.1(5) . . . . ?
C1_1 C6_1 B2_1 O2_1 178.7(4) . . . . ?
C5_1 C6_1 B2_1 O2_1 -1.6(6) . . . . ?
C1_1 C6_1 B2_1 O1_1 -0.8(6) . . . . ?
C5_1 C6_1 B2_1 O1_1 179.0(3) . . . . ?



####################################################################### 
# 
# 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_6Benz
_database_code_depnum_ccdc_archive 'CCDC 2541880'
loop_
_audit_author_name
_audit_author_address
'Andreas Haefner'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2026-03-28 deposited with the CCDC.	2026-06-03 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.6l (K.Radacki, 2005-26)'
_audit_creation_date             2026-02-04
_shelx_SHELXL_version_number     2025/1
_chemical_formula_moiety         'C13 H10 B2 N2 O2'
_chemical_formula_sum            'C13 H10 B2 N2 O2'
_chemical_formula_weight         247.85
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                   4.8451(7)
_cell_length_b                   16.779(3)
_cell_length_c                   14.398(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.093(8)
_cell_angle_gamma                90
_cell_volume                     1169.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12301
_cell_measurement_theta_min      4.0400
_cell_measurement_theta_max      71.7140
_cell_special_details            
;
 Uncertainties of the unit cell parameters were calculated as standard 
 deviations on 63 cells obtained from subsets of all reflections. These sets 
 of reflections were based on runs in experiment.
;

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.30a (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 1 -1 0.0329
-1 10 0 0.0732
0 -7 7 0.0361
1 -10 -2 0.1009
0 10 3 0.0174
0 10 -2 0.0336
3 1 0 0.2071
0 -11 0 0.0157
0 -1 -9 0.0332

_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.970
_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    -95.00 -66.00   0.50    0.05    --  -50.00 -52.00 175.53   58
  2  ω    -79.00 -50.00   0.50    0.05    --  -34.00 -52.00  95.29   58
  3  ω    -84.00 -55.00   0.50    0.05    --  -38.00 -48.00  18.67   58
  4  ω    -89.00 -58.00   0.50    0.05    --  -42.00 -44.00-100.63   62
  5  ω    -89.00 -58.00   0.50    0.05    --  -42.00 -44.00-135.59   62
  6  ω    -93.00 -61.00   0.50    0.05    --  -46.00 -42.00-172.65   64
  7  ω     -6.00  20.00   0.50    0.05    --  -14.00  78.00-161.99   52
  8  ω    -23.00   4.00   0.50    0.05    --  -18.00  98.00 -63.91   54
  9  ω    -32.00  -4.00   0.50    0.05    --  -18.00 110.00  46.88   56
 10  ω    -84.00 -16.00   0.50    0.05    --  -60.08 126.00 150.00  136
 11  ω   -101.00 -35.00   0.50    0.05    --  -78.50 128.00  99.01  132
 12  ω   -101.00 -35.00   0.50    0.05    --  -78.50 127.00  65.76  132
 13  ω   -101.00 -35.00   0.50    0.05    --  -78.50 127.00  20.54  132
 14  ω    -99.00 -35.00   0.50    0.05    --  -78.50 122.00 151.02  128
 15  ω   -101.00 -35.00   0.50    0.05    --  -78.50 127.00  20.54  132
 16  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00  -3.75  128
 17  ω   -100.00 -35.00   0.50    0.05    --  -78.00 124.00 -55.97  130
 18  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00 -60.00  112
 19  ω    -99.00 -35.00   0.50    0.05    --  -78.50 122.00 -80.70  128
 20  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00 -90.00  112
 21  ω    -99.00 -35.00   0.50    0.05    --  -78.50 123.00-175.65  128
 22  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00-150.00  112
 23  ω    -91.00 -37.00   0.50    0.05    --  -78.50 108.00 -74.34  108
 24  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00  30.00  112
 25  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00  60.00  112
 26  ω    -89.00 -37.00   0.50    0.05    --  -78.50 106.00  74.15  104
 27  ω   -122.00 -43.00   0.50    0.05    --  -75.18 -15.00  30.00  158
 28  ω   -118.00 -89.00   0.50    0.05    --  -74.00 -57.00  92.86   58
 29  ω   -118.00 -89.00   0.50    0.05    --  -74.00 -56.00 143.37   58
 30  ω   -118.00 -90.00   0.50    0.05    --  -74.00 -54.00  42.29   56
 31  ω   -122.00 -93.00   0.50    0.05    --  -78.50 -56.00  25.81   58
 32  ω   -121.00 -93.00   0.50    0.05    --  -78.50 -60.00   2.95   56
 33  ω   -107.00 -78.00   0.50    0.05    --  -62.00 -52.00 -38.69   58
 34  ω    -99.00 -70.00   0.50    0.05    --  -54.00 -52.00   4.68   58
 35  ω   -119.00 -90.00   0.50    0.05    --  -74.00 -53.00 -66.87   58
 36  ω   -123.00 -94.00   0.50    0.05    --  -78.50 -54.00-103.99   58
 37  ω   -123.00 -95.00   0.50    0.05    --  -78.50 -52.00-116.75   56
 38  ω   -124.00 -95.00   0.50    0.05    --  -78.50 -51.00-131.34   58
 39  ω   -121.00 -93.00   0.50    0.05    --  -78.50 -59.00-163.30   56
 40  ω   -124.00 -96.00   0.50    0.05    --  -78.50 -48.00 -81.94   56
 41  ω   -123.00 -95.00   0.50    0.05    --  -78.50 -52.00 -48.13   56
 42  ω    -99.00 -71.00   0.50    0.05    --  -54.00 -50.00 -23.32   56
 43  ω   -125.00 -95.00   0.50    0.05    --  -78.50 -45.00  65.48   60
 44  ω   -117.00 -86.00   0.50    0.05    --  -70.00 -43.00  47.08   62
 45  ω    -99.00 -71.00   0.50    0.05    --  -54.00 -51.00  76.79   56
 46  ω   -124.00 -96.00   0.50    0.05    --  -78.50 -48.00 116.63   56
 47  ω   -121.00 -90.00   0.50    0.05    --  -74.00 -43.00 164.05   62
 48  ω    -99.00 -70.00   0.50    0.05    --  -54.00 -52.00 143.22   58
 49  ω   -126.00 -93.00   0.50    0.05    --  -78.50 -39.00 150.67   66
 50  ω   -126.00 -94.00   0.50    0.05    --  -78.50 -41.00 -31.24   64
 51  ω   -125.00 -94.00   0.50    0.05    --  -78.50 -43.00-156.82   62
 52  ω     41.00  92.00   0.50    0.05    --   82.25-103.00-153.07  102
 53  ω     37.00  92.00   0.50    0.05    --   78.63-112.00 -60.00  110
 54  ω     37.00  92.00   0.50    0.05    --   78.63-112.00 -30.00  110
 55  ω     37.00  92.00   0.50    0.05    --   78.63-112.00   0.00  110
 56  ω     37.00  92.00   0.50    0.05    --   78.63-112.00  30.00  110
 57  ω     45.00 126.00   0.50    0.05    --   78.63  15.00-150.00  162
 58  ω     45.00 126.00   0.50    0.05    --   78.63  15.00   0.00  162
 59  ω     29.00  58.00   0.50    0.05    --   14.00  58.00 -29.32   58
 60  ω     29.00  56.00   0.50    0.05    --   14.00  60.00 164.99   54
 61  ω     45.00 126.00   0.50    0.05    --   78.63  15.00 120.00  162
 62  ω     45.00 126.00   0.50    0.05    --   78.63  15.00  90.00  162
 63  ω     45.00 126.00   0.50    0.05    --   78.63  15.00 -90.00  162
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.3062319000
_diffrn_orient_matrix_UB_12      0.0108015000
_diffrn_orient_matrix_UB_13      0.0299128000
_diffrn_orient_matrix_UB_21      0.0612422000
_diffrn_orient_matrix_UB_22      -0.0854703000
_diffrn_orient_matrix_UB_23      -0.0324561000
_diffrn_orient_matrix_UB_31      0.0608475000
_diffrn_orient_matrix_UB_32      0.0317016000
_diffrn_orient_matrix_UB_33      -0.0975741000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            26145
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.047
_diffrn_reflns_theta_max         72.445
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2284
_reflns_number_gt                1928
_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 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    "SHELXT 2014/5 (Sheldrick, 2014)'"
_computing_structure_refinement  'SHELXL-2025/1 (Sheldrick, 2025)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2025/1 (Sheldrick, 2025)'

_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)+(0.0965P)²+0.3479P] 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         2284
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.235
_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
C1_1 C 0.8897(4) 0.34795(11) 0.48101(12) 0.0386(4) Uani 1 1 d . . . . .
H1_1 H 0.928126 0.371123 0.540285 0.046 Uiso 1 1 calc R U . . .
N1_1 N 0.6434(3) 0.25765(8) 0.39194(9) 0.0348(4) Uani 1 1 d . . . . .
O1_1 O 0.6937(2) 0.24708(7) 0.22415(7) 0.0341(3) Uani 1 1 d . . . . .
B1_1 B 0.7726(4) 0.28069(12) 0.30790(13) 0.0349(4) Uani 1 1 d . . . . .
O2_1 O 0.4029(3) 0.16156(7) 0.13343(8) 0.0406(4) Uani 1 1 d . . . . .
H2_1 H 0.509(4) 0.1883(12) 0.0836(13) 0.061 Uiso 1 1 calc R U . . .
N2_1 N 0.7022(3) 0.29272(9) 0.47712(9) 0.0376(4) Uani 1 1 d . . . . .
C2_1 C 1.0463(4) 0.37803(10) 0.40526(12) 0.0370(4) Uani 1 1 d . . . . .
B2_1 B 0.4867(4) 0.19058(12) 0.21746(13) 0.0355(4) Uani 1 1 d . . . . .
C3_1 C 1.2419(4) 0.43890(11) 0.41887(13) 0.0412(4) Uani 1 1 d . . . . .
H3_1 H 1.274277 0.461387 0.478832 0.049 Uiso 1 1 calc R U . . .
C4_1 C 1.3862(4) 0.46572(11) 0.34466(14) 0.0436(5) Uani 1 1 d . . . . .
H4_1 H 1.517150 0.507443 0.353425 0.052 Uiso 1 1 calc R U . . .
C5_1 C 1.3426(4) 0.43234(11) 0.25650(13) 0.0431(5) Uani 1 1 d . . . . .
H5_1 H 1.447786 0.450251 0.206153 0.052 Uiso 1 1 calc R U . . .
C6_1 C 1.1471(4) 0.37344(11) 0.24242(13) 0.0395(4) Uani 1 1 d . . . . .
H6_1 H 1.115439 0.351698 0.182051 0.047 Uiso 1 1 calc R U . . .
C7_1 C 0.9955(3) 0.34557(10) 0.31638(12) 0.0348(4) Uani 1 1 d . . . . .
C8_1 C 0.4399(4) 0.19578(10) 0.39349(12) 0.0368(4) Uani 1 1 d . . . . .
C9_1 C 0.3559(4) 0.16176(10) 0.30825(12) 0.0351(4) Uani 1 1 d . . . . .
C10_1 C 0.1516(4) 0.10237(11) 0.30800(13) 0.0401(4) Uani 1 1 d . . . . .
H10_1 H 0.092307 0.078827 0.250671 0.048 Uiso 1 1 calc R U . . .
C11_1 C 0.0351(4) 0.07746(11) 0.38878(13) 0.0458(5) Uani 1 1 d . . . . .
H11_1 H -0.104728 0.037752 0.387425 0.055 Uiso 1 1 calc R U . . .
C12_1 C 0.1261(5) 0.11152(12) 0.47238(14) 0.0504(5) Uani 1 1 d . . . . .
H12_1 H 0.047306 0.094506 0.528491 0.060 Uiso 1 1 calc R U . . .
C13_1 C 0.3296(4) 0.16986(11) 0.47582(13) 0.0451(5) Uani 1 1 d . . . . .
H13_1 H 0.392338 0.191709 0.533686 0.054 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
C1_1 N2_1 1.298(2) . ?
C1_1 C2_1 1.442(3) . ?
C1_1 H1_1 0.9500 . ?
N1_1 N2_1 1.3805(19) . ?
N1_1 C8_1 1.432(2) . ?
N1_1 B1_1 1.436(2) . ?
O1_1 B1_1 1.373(2) . ?
O1_1 B2_1 1.381(2) . ?
B1_1 C7_1 1.535(3) . ?
O2_1 B2_1 1.353(2) . ?
O2_1 H2_1 1.00(3) . ?
C2_1 C3_1 1.402(3) . ?
C2_1 C7_1 1.404(2) . ?
B2_1 C9_1 1.551(3) . ?
C3_1 C4_1 1.374(3) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.396(3) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.379(3) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.396(2) . ?
C6_1 H6_1 0.9500 . ?
C8_1 C13_1 1.388(3) . ?
C8_1 C9_1 1.400(2) . ?
C9_1 C10_1 1.405(2) . ?
C10_1 C11_1 1.376(3) . ?
C10_1 H10_1 0.9500 . ?
C11_1 C12_1 1.390(3) . ?
C11_1 H11_1 0.9500 . ?
C12_1 C13_1 1.389(3) . ?
C12_1 H12_1 0.9500 . ?
C13_1 H13_1 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 C1_1 C2_1 127.17(16) . . ?
N2_1 C1_1 H1_1 116.4 . . ?
C2_1 C1_1 H1_1 116.4 . . ?
N2_1 N1_1 C8_1 114.51(13) . . ?
N2_1 N1_1 B1_1 123.49(15) . . ?
C8_1 N1_1 B1_1 122.00(14) . . ?
B1_1 O1_1 B2_1 121.43(14) . . ?
O1_1 B1_1 N1_1 120.92(17) . . ?
O1_1 B1_1 C7_1 122.25(16) . . ?
N1_1 B1_1 C7_1 116.81(16) . . ?
B2_1 O2_1 H2_1 109.5 . . ?
C1_1 N2_1 N1_1 117.66(14) . . ?
C3_1 C2_1 C7_1 120.33(17) . . ?
C3_1 C2_1 C1_1 121.38(16) . . ?
C7_1 C2_1 C1_1 118.28(16) . . ?
O2_1 B2_1 O1_1 120.21(16) . . ?
O2_1 B2_1 C9_1 121.54(17) . . ?
O1_1 B2_1 C9_1 118.25(15) . . ?
C4_1 C3_1 C2_1 119.38(18) . . ?
C4_1 C3_1 H3_1 120.3 . . ?
C2_1 C3_1 H3_1 120.3 . . ?
C3_1 C4_1 C5_1 120.73(18) . . ?
C3_1 C4_1 H4_1 119.6 . . ?
C5_1 C4_1 H4_1 119.6 . . ?
C6_1 C5_1 C4_1 120.10(17) . . ?
C6_1 C5_1 H5_1 119.9 . . ?
C4_1 C5_1 H5_1 119.9 . . ?
C5_1 C6_1 C7_1 120.38(17) . . ?
C5_1 C6_1 H6_1 119.8 . . ?
C7_1 C6_1 H6_1 119.8 . . ?
C6_1 C7_1 C2_1 119.05(17) . . ?
C6_1 C7_1 B1_1 124.41(16) . . ?
C2_1 C7_1 B1_1 116.55(16) . . ?
C13_1 C8_1 C9_1 120.81(17) . . ?
C13_1 C8_1 N1_1 121.81(16) . . ?
C9_1 C8_1 N1_1 117.37(15) . . ?
C8_1 C9_1 C10_1 118.27(16) . . ?
C8_1 C9_1 B2_1 119.81(16) . . ?
C10_1 C9_1 B2_1 121.92(16) . . ?
C11_1 C10_1 C9_1 121.60(17) . . ?
C11_1 C10_1 H10_1 119.2 . . ?
C9_1 C10_1 H10_1 119.2 . . ?
C10_1 C11_1 C12_1 118.71(18) . . ?
C10_1 C11_1 H11_1 120.6 . . ?
C12_1 C11_1 H11_1 120.6 . . ?
C13_1 C12_1 C11_1 121.54(18) . . ?
C13_1 C12_1 H12_1 119.2 . . ?
C11_1 C12_1 H12_1 119.2 . . ?
C8_1 C13_1 C12_1 119.04(18) . . ?
C8_1 C13_1 H13_1 120.5 . . ?
C12_1 C13_1 H13_1 120.5 . . ?

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
B2_1 O1_1 B1_1 N1_1 0.5(3) . . . . ?
B2_1 O1_1 B1_1 C7_1 -177.94(15) . . . . ?
N2_1 N1_1 B1_1 O1_1 -175.97(14) . . . . ?
C8_1 N1_1 B1_1 O1_1 3.8(3) . . . . ?
N2_1 N1_1 B1_1 C7_1 2.6(2) . . . . ?
C8_1 N1_1 B1_1 C7_1 -177.68(14) . . . . ?
C2_1 C1_1 N2_1 N1_1 0.4(3) . . . . ?
C8_1 N1_1 N2_1 C1_1 178.39(15) . . . . ?
B1_1 N1_1 N2_1 C1_1 -1.8(2) . . . . ?
N2_1 C1_1 C2_1 C3_1 179.25(17) . . . . ?
N2_1 C1_1 C2_1 C7_1 0.2(3) . . . . ?
B1_1 O1_1 B2_1 O2_1 176.44(15) . . . . ?
B1_1 O1_1 B2_1 C9_1 -3.7(2) . . . . ?
C7_1 C2_1 C3_1 C4_1 -0.9(3) . . . . ?
C1_1 C2_1 C3_1 C4_1 -179.98(16) . . . . ?
C2_1 C3_1 C4_1 C5_1 -0.8(3) . . . . ?
C3_1 C4_1 C5_1 C6_1 2.0(3) . . . . ?
C4_1 C5_1 C6_1 C7_1 -1.3(3) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.4(3) . . . . ?
C5_1 C6_1 C7_1 B1_1 179.63(16) . . . . ?
C3_1 C2_1 C7_1 C6_1 1.5(3) . . . . ?
C1_1 C2_1 C7_1 C6_1 -179.38(15) . . . . ?
C3_1 C2_1 C7_1 B1_1 -178.49(15) . . . . ?
C1_1 C2_1 C7_1 B1_1 0.6(2) . . . . ?
O1_1 B1_1 C7_1 C6_1 -3.4(3) . . . . ?
N1_1 B1_1 C7_1 C6_1 178.13(15) . . . . ?
O1_1 B1_1 C7_1 C2_1 176.66(15) . . . . ?
N1_1 B1_1 C7_1 C2_1 -1.8(2) . . . . ?
N2_1 N1_1 C8_1 C13_1 -4.8(2) . . . . ?
B1_1 N1_1 C8_1 C13_1 175.40(17) . . . . ?
N2_1 N1_1 C8_1 C9_1 175.44(14) . . . . ?
B1_1 N1_1 C8_1 C9_1 -4.3(2) . . . . ?
C13_1 C8_1 C9_1 C10_1 1.8(3) . . . . ?
N1_1 C8_1 C9_1 C10_1 -178.45(14) . . . . ?
C13_1 C8_1 C9_1 B2_1 -178.74(16) . . . . ?
N1_1 C8_1 C9_1 B2_1 1.0(2) . . . . ?
O2_1 B2_1 C9_1 C8_1 -177.20(16) . . . . ?
O1_1 B2_1 C9_1 C8_1 2.9(2) . . . . ?
O2_1 B2_1 C9_1 C10_1 2.3(3) . . . . ?
O1_1 B2_1 C9_1 C10_1 -177.61(15) . . . . ?
C8_1 C9_1 C10_1 C11_1 -0.1(3) . . . . ?
B2_1 C9_1 C10_1 C11_1 -179.58(17) . . . . ?
C9_1 C10_1 C11_1 C12_1 -0.9(3) . . . . ?
C10_1 C11_1 C12_1 C13_1 0.2(3) . . . . ?
C9_1 C8_1 C13_1 C12_1 -2.4(3) . . . . ?
N1_1 C8_1 C13_1 C12_1 177.84(17) . . . . ?
C11_1 C12_1 C13_1 C8_1 1.4(3) . . . . ?



####################################################################### 
# 
# 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_2Benz
_database_code_depnum_ccdc_archive 'CCDC 2541881'
loop_
_audit_author_name
_audit_author_address
'Andreas Haefner'
;Julius Maximilians University Wuerzburg
Germany
;
_audit_update_record             
;
2026-03-28 deposited with the CCDC.	2026-06-03 downloaded from the CCDC.
;

_audit_creation_method           'CIF-fill 1.6l (K.Radacki, 2005-26)'
_audit_creation_date             2026-02-04
_shelx_SHELXL_version_number     2025/1
_chemical_formula_moiety         'C19 H14 B2 Br2 N2'
_chemical_formula_sum            'C19 H14 B2 Br2 N2'
_chemical_formula_weight         451.76
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'
Br Br -0.6763 1.2805 '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                   10.1408(17)
_cell_length_b                   10.5705(17)
_cell_length_c                   16.4231(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1760.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    36335
_cell_measurement_theta_min      2.6740
_cell_measurement_theta_max      73.0920
_cell_special_details            
;
 Uncertainties of the unit cell parameters were calculated as standard 
 deviations on 63 cells obtained from subsets of all reflections. These sets 
 of reflections were based on runs in experiment.
;

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    5.850
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.252
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.30a (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 -2 1 0.0239
0 2 -1 0.0428
2 0 -1 0.1920
-2 1 1 0.1258
0 -7 -2 0.0354
1 7 2 0.0472
0 0 -11 0.0415
0 0 11 0.0480
2 -6 -4 0.0663
2 -6 5 0.0693
-1 5 7 0.0628
7 0 -1 0.1630
0 0 11 0.0278
-6 -2 1 0.1211

_shelx_estimated_absorpt_T_min   0.264
_shelx_estimated_absorpt_T_max   0.685
_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    -93.00 -61.00   0.50    0.05    --  -46.00 -42.00-135.85   64
  2  ω    -79.00 -51.00   0.50    0.05    --  -34.00 -51.00-107.87   56
  3  ω    -72.00 -43.00   0.50    0.05    --  -26.00 -47.00 -79.34   58
  4  ω    -92.00 -63.00   0.50    0.05    --  -46.00 -49.00 -22.06   58
  5  ω    -72.00 -43.00   0.50    0.05    --  -26.00 -49.00 172.06   58
  6  ω     20.00  83.00   0.50    0.05    --   58.93-126.00  60.00  126
  7  ω     37.00  92.00   0.50    0.05    --   78.63-112.00 150.00  110
  8  ω     36.00  98.00   0.50    0.05    --   78.63-120.00-179.00  124
  9  ω     36.00  98.00   0.50    0.05    --   78.63-120.00-179.00  124
 10  ω     29.00  92.00   0.50    0.05    --   71.60-120.00-179.00  126
 11  ω     43.00  89.00   0.50    0.05    --   82.25 -99.00-179.28   92
 12  ω     16.00  79.00   0.50    0.05    --   58.93-120.00-179.00  126
 13  ω     37.00  92.00   0.50    0.05    --   78.63-112.00   0.00  110
 14  ω     37.00  92.00   0.50    0.05    --   78.63-112.00  60.00  110
 15  ω     37.00  92.00   0.50    0.05    --   78.63-112.00  90.00  110
 16  ω     45.00 126.00   0.50    0.05    --   78.63  15.00  90.00  162
 17  ω     45.00 126.00   0.50    0.05    --   78.63  15.00  30.00  162
 18  ω     45.00 126.00   0.50    0.05    --   78.63  15.00-180.00  162
 19  ω     49.00 129.00   0.50    0.05    --   82.25  15.00 -70.17  160
 20  ω     49.00 129.00   0.50    0.05    --   82.25  15.00 -70.17  160
 21  ω     67.00  96.00   0.50    0.05    --   50.00  50.00  45.96   58
 22  ω     55.00  83.00   0.50    0.05    --   38.00  52.00 161.04   56
 23  ω     34.00  60.00   0.50    0.05    --   18.00  55.00 153.77   52
 24  ω     29.00  57.00   0.50    0.05    --   14.00  59.00  97.75   56
 25  ω     34.00  60.00   0.50    0.05    --   18.00  57.00  33.44   52
 26  ω     20.00  48.00   0.50    0.05    --    6.00  62.00   0.56   56
 27  ω   -100.00 -35.00   0.50    0.05    --  -78.50 125.00-126.20  130
 28  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00-171.66  128
 29  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00 -39.34  128
 30  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00-145.35  128
 31  ω    -43.00 -12.00   0.50    0.05    --  -22.00 123.00  -5.90   62
 32  ω    -95.00 -32.00   0.50    0.05    --  -75.18 120.00 -96.00  126
 33  ω    -90.00 -26.00   0.50    0.05    --  -69.75 120.00 -96.00  128
 34  ω    -90.00 -26.00   0.50    0.05    --  -69.75 120.00 -96.00  128
 35  ω    -80.00 -17.00   0.50    0.05    --  -60.27 120.00 -96.00  126
 36  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00-180.00  112
 37  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00   0.00  112
 38  ω    -89.00 -33.00   0.50    0.05    --  -75.18 112.00  30.00  112
 39  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00  40.71  128
 40  ω    -91.00 -37.00   0.50    0.05    --  -78.50 108.00  74.45  108
 41  ω    -99.00 -35.00   0.50    0.05    --  -78.50 121.00 153.09  128
 42  ω    -39.00 -12.00   0.50    0.05    --  -18.00 123.00 174.46   54
 43  ω   -120.00 -94.00   0.50    0.05    --  -78.50 -64.00 174.35   52
 44  ω   -113.00 -85.00   0.50    0.05    --  -70.00 -58.00 154.91   56
 45  ω   -113.00 -85.00   0.50    0.05    --  -70.00 -59.00  93.29   56
 46  ω   -118.00 -89.00   0.50    0.05    --  -74.00 -56.00 131.37   58
 47  ω   -121.00 -93.00   0.50    0.05    --  -78.50 -60.00  17.26   56
 48  ω   -123.00 -94.00   0.50    0.05    --  -78.50 -54.00  77.18   58
 49  ω   -123.00 -95.00   0.50    0.05    --  -78.50 -52.00 154.36   56
 50  ω   -107.00 -78.00   0.50    0.05    --  -62.00 -52.00  62.30   58
 51  ω   -121.00 -93.00   0.50    0.05    --  -78.50 -59.00 -76.85   56
 52  ω   -122.00 -94.00   0.50    0.05    --  -78.50 -57.00-126.35   56
 53  ω   -118.00 -90.00   0.50    0.05    --  -74.00 -55.00-171.17   56
 54  ω   -103.00 -75.00   0.50    0.05    --  -58.00 -51.00-128.27   56
 55  ω   -124.00 -96.00   0.50    0.05    --  -78.50 -48.00 -32.94   56
 56  ω   -121.00 -90.00   0.50    0.05    --  -74.00 -43.00 -20.84   62
 57  ω   -121.00 -90.00   0.50    0.05    --  -74.00 -43.00 -53.23   62
 58  ω   -126.00 -93.00   0.50    0.05    --  -78.50 -40.00 -31.56   66
 59  ω   -121.00 -89.00   0.50    0.05    --  -74.00 -41.00  38.55   64
 60  ω   -124.00 -96.00   0.50    0.05    --  -78.50 -49.00 174.01   56
 61  ω   -103.00 -75.00   0.50    0.05    --  -58.00 -50.00 178.99   56
 62  ω   -108.00 -79.00   0.50    0.05    --  -62.00 -47.00  95.76   58
 63  ω   -122.00 -43.00   0.50    0.05    --  -75.18 -15.00-120.00  158
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.1008503000
_diffrn_orient_matrix_UB_12      -0.0160110000
_diffrn_orient_matrix_UB_13      -0.0694139000
_diffrn_orient_matrix_UB_21      0.1045838000
_diffrn_orient_matrix_UB_22      0.0433892000
_diffrn_orient_matrix_UB_23      -0.0621037000
_diffrn_orient_matrix_UB_31      0.0444827000
_diffrn_orient_matrix_UB_32      -0.1381161000
_diffrn_orient_matrix_UB_33      -0.0114714000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            41729
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.976
_diffrn_reflns_theta_max         73.348
_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 0.975
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3453
_reflns_number_gt                3453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    1.000
_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 1.171.42.30a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_solution    "SHELXT 2014/5 (Sheldrick, 2014)'"
_computing_structure_refinement  'SHELXL-2025/1 (Sheldrick, 2025)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2025/1 (Sheldrick, 2025)'

_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)+(0.0205P)²+0.7417P] 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 
;
 Flack x determined using 1455 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, 
 Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3453
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0141
_refine_ls_R_factor_gt           0.0141
_refine_ls_wR_factor_ref         0.0385
_refine_ls_wR_factor_gt          0.0385
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.071
_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 0.60440(19) 0.64572(18) 0.62023(12) 0.0125(4) Uani 1 1 d . . . . .
C1_1 C 0.4822(2) 0.6364(2) 0.49859(14) 0.0149(5) Uani 1 1 d . . . . .
H1_1 H 0.433207 0.680005 0.458071 0.018 Uiso 1 1 calc R U . . .
B1_1 B 0.6389(3) 0.5142(2) 0.61760(16) 0.0142(5) Uani 1 1 d . . . . .
N2_1 N 0.53374(19) 0.70265(17) 0.55711(12) 0.0125(4) Uani 1 1 d . . . . .
C2_1 C 0.4945(2) 0.5033(2) 0.49126(14) 0.0150(5) Uani 1 1 d . . . . .
C3_1 C 0.4299(2) 0.4394(2) 0.42740(15) 0.0184(5) Uani 1 1 d . . . . .
H3_1 H 0.377367 0.484921 0.389525 0.022 Uiso 1 1 calc R U . . .
C4_1 C 0.4438(3) 0.3104(2) 0.42047(16) 0.0208(5) Uani 1 1 d . . . . .
H4_1 H 0.399385 0.266151 0.378250 0.025 Uiso 1 1 calc R U . . .
C5_1 C 0.5233(2) 0.2445(2) 0.47566(16) 0.0218(5) Uani 1 1 d . . . . .
H5_1 H 0.532792 0.155434 0.470329 0.026 Uiso 1 1 calc R U . . .
C6_1 C 0.5883(2) 0.3068(2) 0.53780(16) 0.0188(5) Uani 1 1 d . . . . .
H6_1 H 0.643238 0.260435 0.573929 0.023 Uiso 1 1 calc R U . . .
C7_1 C 0.5740(2) 0.4382(2) 0.54814(14) 0.0145(4) Uani 1 1 d . . . . .
C1_2 C 0.7414(2) 0.4557(2) 0.67817(14) 0.0145(4) Uani 1 1 d . . . . .
C2_2 C 0.7117(3) 0.3518(2) 0.72761(16) 0.0192(5) Uani 1 1 d . . . . .
H2_2 H 0.624703 0.318573 0.727859 0.023 Uiso 1 1 calc R U . . .
C3_2 C 0.8080(3) 0.2965(3) 0.77649(16) 0.0247(6) Uani 1 1 d . . . . .
H3_2 H 0.785915 0.227390 0.810838 0.030 Uiso 1 1 calc R U . . .
C4_2 C 0.9362(3) 0.3424(3) 0.77504(16) 0.0260(6) Uani 1 1 d . . . . .
H4_2 H 1.002323 0.303400 0.807416 0.031 Uiso 1 1 calc R U . . .
C5_2 C 0.9677(3) 0.4452(3) 0.72632(16) 0.0234(6) Uani 1 1 d . . . . .
H5_2 H 1.055269 0.477154 0.725638 0.028 Uiso 1 1 calc R U . . .
C6_2 C 0.8711(3) 0.5013(2) 0.67855(15) 0.0173(5) Uani 1 1 d . . . . .
H6_2 H 0.893320 0.571923 0.645509 0.021 Uiso 1 1 calc R U . . .
C1_3 C 0.6309(2) 0.7429(2) 0.67993(14) 0.0141(4) Uani 1 1 d . . . . .
Br1_3 Br 0.35662(2) 0.92615(2) 0.54954(2) 0.01659(7) Uani 1 1 d . . . . .
B1_3 B 0.5368(3) 0.8517(2) 0.56418(17) 0.0150(5) Uani 1 1 d . . . . .
Br2_3 Br 0.65613(2) 0.91299(2) 0.47212(2) 0.01619(7) Uani 1 1 d . . . . .
C2_3 C 0.6743(2) 0.7200(2) 0.75892(15) 0.0171(5) Uani 1 1 d . . . . .
H2_3 H 0.693555 0.636681 0.777123 0.021 Uiso 1 1 calc R U . . .
C3_3 C 0.6883(2) 0.8242(3) 0.81032(16) 0.0201(5) Uani 1 1 d . . . . .
H3_3 H 0.718341 0.811915 0.864535 0.024 Uiso 1 1 calc R U . . .
C4_3 C 0.6587(2) 0.9467(2) 0.78323(15) 0.0191(5) Uani 1 1 d . . . . .
H4_3 H 0.670018 1.016778 0.818774 0.023 Uiso 1 1 calc R U . . .
C5_3 C 0.6129(2) 0.9658(2) 0.70447(16) 0.0177(5) Uani 1 1 d . . . . .
H5_3 H 0.591775 1.048722 0.686448 0.021 Uiso 1 1 calc R U . . .
C6_3 C 0.5978(2) 0.8632(2) 0.65176(15) 0.0142(5) Uani 1 1 d . . . . .


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 1.397(3) . ?
N1_1 B1_1 1.434(3) . ?
N1_1 C1_3 1.445(3) . ?
C1_1 N2_1 1.299(3) . ?
C1_1 C2_1 1.418(4) . ?
C1_1 H1_1 0.9500 . ?
B1_1 C7_1 1.543(3) . ?
B1_1 C1_2 1.566(3) . ?
N2_1 B1_3 1.580(3) . ?
C2_1 C3_1 1.409(3) . ?
C2_1 C7_1 1.413(3) . ?
C3_1 C4_1 1.375(4) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.399(4) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.382(4) . ?
C5_1 H5_1 0.9500 . ?
C6_1 C7_1 1.407(3) . ?
C6_1 H6_1 0.9500 . ?
C1_2 C2_2 1.398(3) . ?
C1_2 C6_2 1.400(4) . ?
C2_2 C3_2 1.393(4) . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.388(4) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.387(4) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.388(4) . ?
C5_2 H5_2 0.9500 . ?
C6_2 H6_2 0.9500 . ?
C1_3 C2_3 1.391(3) . ?
C1_3 C6_3 1.394(3) . ?
Br1_3 B1_3 2.004(3) . ?
B1_3 C6_3 1.570(4) . ?
B1_3 Br2_3 2.042(3) . ?
C2_3 C3_3 1.395(3) . ?
C2_3 H2_3 0.9500 . ?
C3_3 C4_3 1.402(4) . ?
C3_3 H3_3 0.9500 . ?
C4_3 C5_3 1.389(3) . ?
C4_3 H4_3 0.9500 . ?
C5_3 C6_3 1.396(3) . ?
C5_3 H5_3 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_1 121.4(2) . . ?
N2_1 N1_1 C1_3 107.01(17) . . ?
B1_1 N1_1 C1_3 131.6(2) . . ?
N2_1 C1_1 C2_1 124.3(2) . . ?
N2_1 C1_1 H1_1 117.9 . . ?
C2_1 C1_1 H1_1 117.9 . . ?
N1_1 B1_1 C7_1 115.0(2) . . ?
N1_1 B1_1 C1_2 121.7(2) . . ?
C7_1 B1_1 C1_2 123.2(2) . . ?
C1_1 N2_1 N1_1 121.56(19) . . ?
C1_1 N2_1 B1_3 126.9(2) . . ?
N1_1 N2_1 B1_3 111.41(18) . . ?
C3_1 C2_1 C7_1 121.6(2) . . ?
C3_1 C2_1 C1_1 119.9(2) . . ?
C7_1 C2_1 C1_1 118.5(2) . . ?
C4_1 C3_1 C2_1 119.3(2) . . ?
C4_1 C3_1 H3_1 120.3 . . ?
C2_1 C3_1 H3_1 120.3 . . ?
C3_1 C4_1 C5_1 119.9(2) . . ?
C3_1 C4_1 H4_1 120.0 . . ?
C5_1 C4_1 H4_1 120.0 . . ?
C6_1 C5_1 C4_1 121.0(2) . . ?
C6_1 C5_1 H5_1 119.5 . . ?
C4_1 C5_1 H5_1 119.5 . . ?
C5_1 C6_1 C7_1 120.7(2) . . ?
C5_1 C6_1 H6_1 119.6 . . ?
C7_1 C6_1 H6_1 119.6 . . ?
C6_1 C7_1 C2_1 117.4(2) . . ?
C6_1 C7_1 B1_1 124.0(2) . . ?
C2_1 C7_1 B1_1 118.6(2) . . ?
C2_2 C1_2 C6_2 118.0(2) . . ?
C2_2 C1_2 B1_1 122.4(2) . . ?
C6_2 C1_2 B1_1 119.3(2) . . ?
C3_2 C2_2 C1_2 120.9(3) . . ?
C3_2 C2_2 H2_2 119.6 . . ?
C1_2 C2_2 H2_2 119.6 . . ?
C4_2 C3_2 C2_2 120.0(3) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C5_2 C4_2 C3_2 120.0(2) . . ?
C5_2 C4_2 H4_2 120.0 . . ?
C3_2 C4_2 H4_2 120.0 . . ?
C4_2 C5_2 C6_2 119.9(2) . . ?
C4_2 C5_2 H5_2 120.1 . . ?
C6_2 C5_2 H5_2 120.1 . . ?
C5_2 C6_2 C1_2 121.2(2) . . ?
C5_2 C6_2 H6_2 119.4 . . ?
C1_2 C6_2 H6_2 119.4 . . ?
C2_3 C1_3 C6_3 123.0(2) . . ?
C2_3 C1_3 N1_1 124.6(2) . . ?
C6_3 C1_3 N1_1 112.2(2) . . ?
C6_3 B1_3 N2_1 98.74(19) . . ?
C6_3 B1_3 Br1_3 116.02(17) . . ?
N2_1 B1_3 Br1_3 111.40(16) . . ?
C6_3 B1_3 Br2_3 114.85(17) . . ?
N2_1 B1_3 Br2_3 105.88(16) . . ?
Br1_3 B1_3 Br2_3 109.08(13) . . ?
C1_3 C2_3 C3_3 117.3(2) . . ?
C1_3 C2_3 H2_3 121.3 . . ?
C3_3 C2_3 H2_3 121.3 . . ?
C2_3 C3_3 C4_3 121.0(2) . . ?
C2_3 C3_3 H3_3 119.5 . . ?
C4_3 C3_3 H3_3 119.5 . . ?
C5_3 C4_3 C3_3 120.1(2) . . ?
C5_3 C4_3 H4_3 120.0 . . ?
C3_3 C4_3 H4_3 120.0 . . ?
C4_3 C5_3 C6_3 120.1(2) . . ?
C4_3 C5_3 H5_3 120.0 . . ?
C6_3 C5_3 H5_3 120.0 . . ?
C1_3 C6_3 C5_3 118.4(2) . . ?
C1_3 C6_3 B1_3 109.2(2) . . ?
C5_3 C6_3 B1_3 132.1(2) . . ?

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 -9.3(3) . . . . ?
C1_3 N1_1 B1_1 C7_1 171.6(2) . . . . ?
N2_1 N1_1 B1_1 C1_2 167.3(2) . . . . ?
C1_3 N1_1 B1_1 C1_2 -11.8(4) . . . . ?
C2_1 C1_1 N2_1 N1_1 -1.7(4) . . . . ?
C2_1 C1_1 N2_1 B1_3 173.1(2) . . . . ?
B1_1 N1_1 N2_1 C1_1 8.7(3) . . . . ?
C1_3 N1_1 N2_1 C1_1 -172.0(2) . . . . ?
B1_1 N1_1 N2_1 B1_3 -166.8(2) . . . . ?
C1_3 N1_1 N2_1 B1_3 12.5(2) . . . . ?
N2_1 C1_1 C2_1 C3_1 177.2(2) . . . . ?
N2_1 C1_1 C2_1 C7_1 -3.9(4) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.5(3) . . . . ?
C1_1 C2_1 C3_1 C4_1 179.3(2) . . . . ?
C2_1 C3_1 C4_1 C5_1 -1.2(4) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.3(4) . . . . ?
C4_1 C5_1 C6_1 C7_1 1.3(4) . . . . ?
C5_1 C6_1 C7_1 C2_1 -1.9(3) . . . . ?
C5_1 C6_1 C7_1 B1_1 177.7(2) . . . . ?
C3_1 C2_1 C7_1 C6_1 1.1(3) . . . . ?
C1_1 C2_1 C7_1 C6_1 -177.8(2) . . . . ?
C3_1 C2_1 C7_1 B1_1 -178.6(2) . . . . ?
C1_1 C2_1 C7_1 B1_1 2.6(3) . . . . ?
N1_1 B1_1 C7_1 C6_1 -175.9(2) . . . . ?
C1_2 B1_1 C7_1 C6_1 7.5(4) . . . . ?
N1_1 B1_1 C7_1 C2_1 3.7(3) . . . . ?
C1_2 B1_1 C7_1 C2_1 -172.8(2) . . . . ?
N1_1 B1_1 C1_2 C2_2 124.7(3) . . . . ?
C7_1 B1_1 C1_2 C2_2 -59.0(3) . . . . ?
N1_1 B1_1 C1_2 C6_2 -60.7(3) . . . . ?
C7_1 B1_1 C1_2 C6_2 115.6(3) . . . . ?
C6_2 C1_2 C2_2 C3_2 0.8(4) . . . . ?
B1_1 C1_2 C2_2 C3_2 175.4(2) . . . . ?
C1_2 C2_2 C3_2 C4_2 -1.6(4) . . . . ?
C2_2 C3_2 C4_2 C5_2 1.5(4) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.6(4) . . . . ?
C4_2 C5_2 C6_2 C1_2 -0.3(4) . . . . ?
C2_2 C1_2 C6_2 C5_2 0.2(4) . . . . ?
B1_1 C1_2 C6_2 C5_2 -174.6(2) . . . . ?
N2_1 N1_1 C1_3 C2_3 165.9(2) . . . . ?
B1_1 N1_1 C1_3 C2_3 -14.9(4) . . . . ?
N2_1 N1_1 C1_3 C6_3 -9.2(2) . . . . ?
B1_1 N1_1 C1_3 C6_3 170.0(2) . . . . ?
C1_1 N2_1 B1_3 C6_3 174.1(2) . . . . ?
N1_1 N2_1 B1_3 C6_3 -10.7(2) . . . . ?
C1_1 N2_1 B1_3 Br1_3 51.6(3) . . . . ?
N1_1 N2_1 B1_3 Br1_3 -133.16(16) . . . . ?
C1_1 N2_1 B1_3 Br2_3 -66.8(3) . . . . ?
N1_1 N2_1 B1_3 Br2_3 108.38(18) . . . . ?
C6_3 C1_3 C2_3 C3_3 -2.0(4) . . . . ?
N1_1 C1_3 C2_3 C3_3 -176.6(2) . . . . ?
C1_3 C2_3 C3_3 C4_3 0.5(4) . . . . ?
C2_3 C3_3 C4_3 C5_3 0.9(4) . . . . ?
C3_3 C4_3 C5_3 C6_3 -0.8(4) . . . . ?
C2_3 C1_3 C6_3 C5_3 2.1(3) . . . . ?
N1_1 C1_3 C6_3 C5_3 177.3(2) . . . . ?
C2_3 C1_3 C6_3 B1_3 -173.1(2) . . . . ?
N1_1 C1_3 C6_3 B1_3 2.1(3) . . . . ?
C4_3 C5_3 C6_3 C1_3 -0.6(3) . . . . ?
C4_3 C5_3 C6_3 B1_3 173.2(2) . . . . ?
N2_1 B1_3 C6_3 C1_3 4.8(2) . . . . ?
Br1_3 B1_3 C6_3 C1_3 123.91(19) . . . . ?
Br2_3 B1_3 C6_3 C1_3 -107.26(19) . . . . ?
N2_1 B1_3 C6_3 C5_3 -169.4(2) . . . . ?
Br1_3 B1_3 C6_3 C5_3 -50.4(3) . . . . ?
Br2_3 B1_3 C6_3 C5_3 78.5(3) . . . . ?



