# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_wdh1111
_database_code_depnum_ccdc_archive 'CCDC 2276919'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
luc.vanmeervelt@kuleuven.be
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H11 B Br F2 N3 O2)'
_chemical_formula_sum            'C24 H22 B2 Br2 F4 N6 O4'
_chemical_formula_weight         715.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 N3 B1 O2 F2 Br1'
_chemical_oxdiff_usercomment     JK-049-mono-2d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.9571(6)
_cell_length_b                   23.2895(12)
_cell_length_c                   13.9900(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.199(7)
_cell_angle_gamma                90
_cell_volume                     2841.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6313
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4240
_cell_measurement_theta_min      2.4810
_shelx_estimated_absorpt_T_max   0.668
_shelx_estimated_absorpt_T_min   0.428
_exptl_absorpt_coefficient_mu    2.922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29616
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.494
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    7.50    --  -17.07 -99.00-150.00   45
  2  ω     34.00  95.00   1.00    7.50    --   18.87-178.00 -30.00   61
  3  ω     -7.00  91.00   1.00    7.50    --   18.87  38.00-120.00   98
  4  ω    -50.00  40.00   1.00    7.50    --   18.87 -57.00  60.00   90
  5  ω    -38.00  52.00   1.00    7.50    --  -17.07  57.00-180.00   90
  6  ω    -87.00  13.00   1.00    7.50    --  -17.07 -77.00  60.00  100
  7  ω     34.00  81.00   1.00    7.50    --   18.87-178.00  60.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0058533000
_diffrn_orient_matrix_UB_12      0.0303394000
_diffrn_orient_matrix_UB_13      -0.0010873000
_diffrn_orient_matrix_UB_21      -0.0247481000
_diffrn_orient_matrix_UB_22      -0.0004609000
_diffrn_orient_matrix_UB_23      -0.0518924000
_diffrn_orient_matrix_UB_31      -0.0773097000
_diffrn_orient_matrix_UB_32      0.0024402000
_diffrn_orient_matrix_UB_33      0.0040559000
_diffrn_oxdiff_ac4_digest_frames 
;
015ddaaae7d16cf30b4a819d4eddc61e4900027ed4c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3841
_reflns_number_total             5805
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5805
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+2.4377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C16(H16), C30(H30), C31(H31), C33(H33), C37(H37)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C39(H39A,H39B,H39C), C40(H40A,H40B,
 H40C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5241(3) 0.55136(10) 0.6845(2) 0.0600(7) Uani 1 1 d . . . . .
C2 C 0.6283(4) 0.52691(14) 0.6442(3) 0.0410(8) Uani 1 1 d . . . . .
N3 N 0.6080(3) 0.47431(11) 0.6134(2) 0.0417(7) Uani 1 1 d . . . . .
N4 N 0.4663(3) 0.45875(12) 0.6325(2) 0.0469(7) Uani 1 1 d . . . . .
B5 B 0.4014(6) 0.5095(2) 0.6844(5) 0.0707(15) Uani 1 1 d . . . . .
C6 C 0.7617(4) 0.55973(13) 0.6366(2) 0.0412(8) Uani 1 1 d . . . . .
O7 O 0.7699(3) 0.61450(9) 0.67422(17) 0.0455(6) Uani 1 1 d . . . . .
C8 C 0.9026(4) 0.63642(15) 0.6592(3) 0.0471(9) Uani 1 1 d . . . . .
C9 C 0.9769(4) 0.59904(16) 0.6155(3) 0.0600(11) Uani 1 1 d . . . . .
H9 H 1.070146 0.604669 0.598303 0.072 Uiso 1 1 calc R U . . .
C10 C 0.8854(4) 0.54883(16) 0.6004(3) 0.0540(10) Uani 1 1 d . . . . .
H10 H 0.906735 0.514904 0.571038 0.065 Uiso 1 1 calc R U . . .
Br11 Br 0.94772(5) 0.71150(2) 0.70084(3) 0.06682(15) Uani 1 1 d . . . . .
C12 C 0.4109(4) 0.40731(14) 0.6121(3) 0.0451(9) Uani 1 1 d . . . . .
H12 H 0.312588 0.401422 0.621498 0.054 Uiso 1 1 calc R U . . .
C13 C 0.4781(4) 0.36010(14) 0.5783(2) 0.0430(8) Uani 1 1 d . . . . .
N14 N 0.6255(4) 0.35822(13) 0.5632(2) 0.0431(7) Uani 1 1 d . . . . .
H14 H 0.681(4) 0.3857(15) 0.570(2) 0.042(11) Uiso 1 1 d . . . . .
C15 C 0.6638(4) 0.30425(15) 0.5456(2) 0.0463(9) Uani 1 1 d . . . . .
C16 C 0.5390(4) 0.26953(15) 0.5480(2) 0.0505(9) Uani 1 1 d . . . . .
H16 H 0.534482 0.230018 0.538144 0.061 Uiso 1 1 calc R U . . .
C17 C 0.4223(4) 0.30323(15) 0.5675(2) 0.0440(8) Uani 1 1 d . . . . .
C18 C 0.8170(5) 0.28871(17) 0.5295(3) 0.0629(11) Uani 1 1 d . . . . .
H18A H 0.861265 0.321437 0.504713 0.094 Uiso 1 1 calc R U . . .
H18B H 0.806341 0.257882 0.482880 0.094 Uiso 1 1 calc R U . . .
H18C H 0.882380 0.276747 0.590556 0.094 Uiso 1 1 calc R U . . .
C19 C 0.2678(4) 0.28366(17) 0.5790(3) 0.0616(11) Uani 1 1 d . . . . .
H19A H 0.228541 0.310646 0.618992 0.092 Uiso 1 1 calc R U . . .
H19B H 0.277126 0.246585 0.609762 0.092 Uiso 1 1 calc R U . . .
H19C H 0.198827 0.281236 0.515568 0.092 Uiso 1 1 calc R U . . .
F20 F 0.2631(3) 0.52711(12) 0.6344(3) 0.1393(15) Uani 1 1 d . . . . .
F21 F 0.3979(4) 0.49438(12) 0.7798(3) 0.1169(12) Uani 1 1 d . . . . .
O22 O 0.0663(3) 0.84588(9) 0.73886(18) 0.0476(6) Uani 1 1 d . . . . .
C23 C 0.1746(4) 0.87019(14) 0.7012(2) 0.0377(8) Uani 1 1 d . . . . .
N24 N 0.1608(3) 0.92374(11) 0.67566(19) 0.0402(7) Uani 1 1 d . . . . .
N25 N 0.0222(3) 0.94096(11) 0.6973(2) 0.0403(7) Uani 1 1 d . . . . .
B26 B -0.0460(5) 0.89100(18) 0.7505(3) 0.0495(11) Uani 1 1 d . . . . .
C27 C 0.3041(4) 0.83634(13) 0.6911(2) 0.0378(8) Uani 1 1 d . . . . .
O28 O 0.2978(2) 0.77880(9) 0.71043(16) 0.0421(5) Uani 1 1 d . . . . .
C29 C 0.4337(4) 0.75703(15) 0.6982(2) 0.0418(8) Uani 1 1 d . . . . .
C30 C 0.5215(4) 0.79760(15) 0.6724(2) 0.0468(9) Uani 1 1 d . . . . .
H30 H 0.618447 0.792767 0.660152 0.056 Uiso 1 1 calc R U . . .
C31 C 0.4383(4) 0.84948(15) 0.6674(2) 0.0444(8) Uani 1 1 d . . . . .
H31 H 0.469589 0.885530 0.651119 0.053 Uiso 1 1 calc R U . . .
Br32 Br 0.45997(5) 0.67876(2) 0.71583(3) 0.06469(15) Uani 1 1 d . . . . .
C33 C -0.0344(4) 0.99165(14) 0.6704(2) 0.0423(8) Uani 1 1 d . . . . .
H33 H -0.129272 0.999582 0.683783 0.051 Uiso 1 1 calc R U . . .
C34 C 0.0288(4) 1.03551(14) 0.6241(2) 0.0420(8) Uani 1 1 d . . . . .
N35 N 0.1730(4) 1.03344(13) 0.6040(2) 0.0462(7) Uani 1 1 d . . . . .
H35 H 0.232(4) 1.0028(18) 0.617(3) 0.070(13) Uiso 1 1 d . . . . .
C36 C 0.2010(4) 1.08301(17) 0.5611(3) 0.0523(10) Uani 1 1 d . . . . .
C37 C 0.0736(5) 1.11739(17) 0.5525(3) 0.0611(11) Uani 1 1 d . . . . .
H37 H 0.062089 1.153877 0.524754 0.073 Uiso 1 1 calc R U . . .
C38 C -0.0351(4) 1.08896(15) 0.5917(3) 0.0497(9) Uani 1 1 d . . . . .
C39 C 0.3496(5) 1.0928(2) 0.5322(3) 0.0810(14) Uani 1 1 d . . . . .
H39A H 0.432553 1.089844 0.589156 0.121 Uiso 1 1 calc R U . . .
H39B H 0.349559 1.130380 0.504039 0.121 Uiso 1 1 calc R U . . .
H39C H 0.362106 1.064431 0.484844 0.121 Uiso 1 1 calc R U . . .
C40 C -0.1913(5) 1.10944(18) 0.5968(3) 0.0733(13) Uani 1 1 d . . . . .
H40A H -0.255868 1.110694 0.531797 0.110 Uiso 1 1 calc R U . . .
H40B H -0.183722 1.147170 0.625091 0.110 Uiso 1 1 calc R U . . .
H40C H -0.234458 1.083607 0.636639 0.110 Uiso 1 1 calc R U . . .
F41 F -0.0350(3) 0.90354(10) 0.84720(17) 0.0740(7) Uani 1 1 d . . . . .
F42 F -0.1910(2) 0.87727(10) 0.7044(2) 0.0779(7) Uani 1 1 d . . . . .


_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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.325(4) . ?
O1 B5 1.469(5) . ?
C2 N3 1.297(4) . ?
C2 C6 1.442(5) . ?
N3 N4 1.403(4) . ?
N4 B5 1.567(5) . ?
N4 C12 1.303(4) . ?
B5 F20 1.340(6) . ?
B5 F21 1.387(6) . ?
C6 O7 1.375(4) . ?
C6 C10 1.344(4) . ?
O7 C8 1.354(4) . ?
C8 C9 1.326(5) . ?
C8 Br11 1.858(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.416(5) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.387(5) . ?
C13 N14 1.385(4) . ?
C13 C17 1.412(5) . ?
N14 H14 0.80(3) . ?
N14 C15 1.341(4) . ?
C15 C16 1.387(5) . ?
C15 C18 1.485(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(5) . ?
C17 C19 1.500(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O22 C23 1.331(4) . ?
O22 B26 1.489(5) . ?
C23 N24 1.296(4) . ?
C23 C27 1.436(4) . ?
N24 N25 1.401(3) . ?
N25 B26 1.578(5) . ?
N25 C33 1.306(4) . ?
B26 F41 1.365(5) . ?
B26 F42 1.350(5) . ?
C27 O28 1.371(4) . ?
C27 C31 1.353(4) . ?
O28 C29 1.365(4) . ?
C29 C30 1.330(5) . ?
C29 Br32 1.847(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.413(5) . ?
C31 H31 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.396(4) . ?
C34 N35 1.385(4) . ?
C34 C38 1.401(5) . ?
N35 H35 0.88(4) . ?
N35 C36 1.351(4) . ?
C36 C37 1.377(5) . ?
C36 C39 1.494(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.390(5) . ?
C38 C40 1.495(5) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?

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
C2 O1 B5 108.3(3) . . ?
O1 C2 C6 118.6(3) . . ?
N3 C2 O1 119.2(3) . . ?
N3 C2 C6 122.1(3) . . ?
C2 N3 N4 104.2(3) . . ?
N3 N4 B5 110.0(3) . . ?
C12 N4 N3 120.8(3) . . ?
C12 N4 B5 129.2(3) . . ?
O1 B5 N4 98.3(3) . . ?
F20 B5 O1 113.5(4) . . ?
F20 B5 N4 112.7(4) . . ?
F20 B5 F21 111.0(4) . . ?
F21 B5 O1 110.4(4) . . ?
F21 B5 N4 110.3(4) . . ?
O7 C6 C2 115.9(3) . . ?
C10 C6 C2 134.1(3) . . ?
C10 C6 O7 110.1(3) . . ?
C8 O7 C6 105.2(2) . . ?
O7 C8 Br11 116.2(2) . . ?
C9 C8 O7 112.0(3) . . ?
C9 C8 Br11 131.8(3) . . ?
C8 C9 H9 127.0 . . ?
C8 C9 C10 106.1(3) . . ?
C10 C9 H9 127.0 . . ?
C6 C10 C9 106.6(3) . . ?
C6 C10 H10 126.7 . . ?
C9 C10 H10 126.7 . . ?
N4 C12 H12 115.5 . . ?
N4 C12 C13 129.1(3) . . ?
C13 C12 H12 115.5 . . ?
C12 C13 C17 127.6(3) . . ?
N14 C13 C12 125.4(3) . . ?
N14 C13 C17 106.3(3) . . ?
C13 N14 H14 123(2) . . ?
C15 N14 C13 110.5(3) . . ?
C15 N14 H14 126(2) . . ?
N14 C15 C16 107.5(3) . . ?
N14 C15 C18 122.7(3) . . ?
C16 C15 C18 129.8(3) . . ?
C15 C16 H16 125.5 . . ?
C17 C16 C15 108.9(3) . . ?
C17 C16 H16 125.5 . . ?
C13 C17 C19 125.9(3) . . ?
C16 C17 C13 106.8(3) . . ?
C16 C17 C19 127.3(3) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 O22 B26 108.3(3) . . ?
O22 C23 C27 118.9(3) . . ?
N24 C23 O22 119.1(3) . . ?
N24 C23 C27 122.0(3) . . ?
C23 N24 N25 104.4(2) . . ?
N24 N25 B26 110.4(3) . . ?
C33 N25 N24 120.1(3) . . ?
C33 N25 B26 129.5(3) . . ?
O22 B26 N25 97.2(3) . . ?
F41 B26 O22 111.2(3) . . ?
F41 B26 N25 111.2(3) . . ?
F42 B26 O22 112.4(3) . . ?
F42 B26 N25 112.5(3) . . ?
F42 B26 F41 111.6(3) . . ?
O28 C27 C23 116.5(3) . . ?
C31 C27 C23 133.1(3) . . ?
C31 C27 O28 110.4(3) . . ?
C29 O28 C27 105.1(2) . . ?
O28 C29 Br32 116.1(2) . . ?
C30 C29 O28 111.7(3) . . ?
C30 C29 Br32 132.2(3) . . ?
C29 C30 H30 126.8 . . ?
C29 C30 C31 106.5(3) . . ?
C31 C30 H30 126.8 . . ?
C27 C31 C30 106.4(3) . . ?
C27 C31 H31 126.8 . . ?
C30 C31 H31 126.8 . . ?
N25 C33 H33 115.7 . . ?
N25 C33 C34 128.6(3) . . ?
C34 C33 H33 115.7 . . ?
C33 C34 C38 128.4(3) . . ?
N35 C34 C33 124.4(3) . . ?
N35 C34 C38 107.2(3) . . ?
C34 N35 H35 122(3) . . ?
C36 N35 C34 109.7(3) . . ?
C36 N35 H35 128(3) . . ?
N35 C36 C37 107.6(3) . . ?
N35 C36 C39 121.2(4) . . ?
C37 C36 C39 131.3(4) . . ?
C36 C37 H37 125.4 . . ?
C36 C37 C38 109.3(3) . . ?
C38 C37 H37 125.4 . . ?
C34 C38 C40 125.8(3) . . ?
C37 C38 C34 106.3(3) . . ?
C37 C38 C40 127.9(4) . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
O1 C2 N3 N4 1.4(4) . . . . ?
O1 C2 C6 O7 0.9(5) . . . . ?
O1 C2 C6 C10 -179.4(4) . . . . ?
C2 O1 B5 N4 -1.2(5) . . . . ?
C2 O1 B5 F20 -120.4(4) . . . . ?
C2 O1 B5 F21 114.1(4) . . . . ?
C2 N3 N4 B5 -2.1(4) . . . . ?
C2 N3 N4 C12 -178.7(3) . . . . ?
C2 C6 O7 C8 179.9(3) . . . . ?
C2 C6 C10 C9 -179.7(4) . . . . ?
N3 C2 C6 O7 -178.6(3) . . . . ?
N3 C2 C6 C10 1.1(6) . . . . ?
N3 N4 B5 O1 2.0(5) . . . . ?
N3 N4 B5 F20 121.9(4) . . . . ?
N3 N4 B5 F21 -113.4(4) . . . . ?
N3 N4 C12 C13 5.5(6) . . . . ?
N4 C12 C13 N14 3.0(6) . . . . ?
N4 C12 C13 C17 172.1(4) . . . . ?
B5 O1 C2 N3 0.0(5) . . . . ?
B5 O1 C2 C6 -179.5(4) . . . . ?
B5 N4 C12 C13 -170.4(4) . . . . ?
C6 C2 N3 N4 -179.1(3) . . . . ?
C6 O7 C8 C9 -0.3(4) . . . . ?
C6 O7 C8 Br11 179.2(2) . . . . ?
O7 C6 C10 C9 0.0(4) . . . . ?
O7 C8 C9 C10 0.3(5) . . . . ?
C8 C9 C10 C6 -0.1(5) . . . . ?
C10 C6 O7 C8 0.2(4) . . . . ?
Br11 C8 C9 C10 -179.1(3) . . . . ?
C12 N4 B5 O1 178.2(4) . . . . ?
C12 N4 B5 F20 -61.9(6) . . . . ?
C12 N4 B5 F21 62.8(6) . . . . ?
C12 C13 N14 C15 170.1(3) . . . . ?
C12 C13 C17 C16 -169.9(3) . . . . ?
C12 C13 C17 C19 8.1(6) . . . . ?
C13 N14 C15 C16 0.6(4) . . . . ?
C13 N14 C15 C18 -178.2(3) . . . . ?
N14 C13 C17 C16 0.9(4) . . . . ?
N14 C13 C17 C19 178.9(3) . . . . ?
N14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C13 -0.6(4) . . . . ?
C15 C16 C17 C19 -178.5(3) . . . . ?
C17 C13 N14 C15 -1.0(4) . . . . ?
C18 C15 C16 C17 178.7(4) . . . . ?
O22 C23 N24 N25 -0.3(4) . . . . ?
O22 C23 C27 O28 7.5(4) . . . . ?
O22 C23 C27 C31 -170.8(3) . . . . ?
C23 O22 B26 N25 6.8(3) . . . . ?
C23 O22 B26 F41 -109.3(3) . . . . ?
C23 O22 B26 F42 124.7(3) . . . . ?
C23 N24 N25 B26 5.1(4) . . . . ?
C23 N24 N25 C33 -172.7(3) . . . . ?
C23 C27 O28 C29 -178.5(3) . . . . ?
C23 C27 C31 C30 178.2(4) . . . . ?
N24 C23 C27 O28 -173.1(3) . . . . ?
N24 C23 C27 C31 8.5(6) . . . . ?
N24 N25 B26 O22 -7.3(4) . . . . ?
N24 N25 B26 F41 108.8(3) . . . . ?
N24 N25 B26 F42 -125.1(3) . . . . ?
N24 N25 C33 C34 -3.4(5) . . . . ?
N25 C33 C34 N35 -4.4(6) . . . . ?
N25 C33 C34 C38 177.1(4) . . . . ?
B26 O22 C23 N24 -4.8(4) . . . . ?
B26 O22 C23 C27 174.6(3) . . . . ?
B26 N25 C33 C34 179.3(4) . . . . ?
C27 C23 N24 N25 -179.7(3) . . . . ?
C27 O28 C29 C30 -0.2(4) . . . . ?
C27 O28 C29 Br32 -178.4(2) . . . . ?
O28 C27 C31 C30 -0.2(4) . . . . ?
O28 C29 C30 C31 0.0(4) . . . . ?
C29 C30 C31 C27 0.1(4) . . . . ?
C31 C27 O28 C29 0.2(3) . . . . ?
Br32 C29 C30 C31 177.9(3) . . . . ?
C33 N25 B26 O22 170.3(3) . . . . ?
C33 N25 B26 F41 -73.7(5) . . . . ?
C33 N25 B26 F42 52.4(5) . . . . ?
C33 C34 N35 C36 -178.6(3) . . . . ?
C33 C34 C38 C37 178.9(3) . . . . ?
C33 C34 C38 C40 -2.7(6) . . . . ?
C34 N35 C36 C37 -0.5(4) . . . . ?
C34 N35 C36 C39 179.4(3) . . . . ?
N35 C34 C38 C37 0.2(4) . . . . ?
N35 C34 C38 C40 178.7(4) . . . . ?
N35 C36 C37 C38 0.7(5) . . . . ?
C36 C37 C38 C34 -0.5(4) . . . . ?
C36 C37 C38 C40 -178.9(4) . . . . ?
C38 C34 N35 C36 0.2(4) . . . . ?
C39 C36 C37 C38 -179.2(4) . . . . ?

_olex2_submission_original_sample_id JK-049-mono-2d
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.799
####################################################################### 
# 
# 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_wdh1116
_database_code_depnum_ccdc_archive 'CCDC 2276920'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2022-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
luc.vanmeervelt@kuleuven.be
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 B Br F2 N3 O S'
_chemical_formula_sum            'C12 H11 B Br F2 N3 O S'
_chemical_formula_weight         374.02
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 N3 O1 F2 Br1 S1'
_chemical_oxdiff_usercomment     JK048
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   6.5546(4)
_cell_length_b                   12.4015(9)
_cell_length_c                   18.2966(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1487.27(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7300
_cell_measurement_theta_min      3.2700
_shelx_estimated_absorpt_T_max   0.474
_shelx_estimated_absorpt_T_min   0.296
_exptl_absorpt_coefficient_mu    2.926
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8962
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_min         2.767
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    5.00    --  -17.15 -99.00 -60.00   45
  2  ω    -90.00  27.00   1.00    5.00    --  -17.15 -19.00   0.00  117
  3  ω     -3.00  88.00   1.00    5.00    --   18.87  57.00 150.00   91
  4  ω    -93.00 -41.00   1.00    5.00    --  -17.15-178.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0164088000
_diffrn_orient_matrix_UB_12      -0.0498542000
_diffrn_orient_matrix_UB_13      -0.0181029000
_diffrn_orient_matrix_UB_21      -0.0146460000
_diffrn_orient_matrix_UB_22      0.0278010000
_diffrn_orient_matrix_UB_23      -0.0334407000
_diffrn_orient_matrix_UB_31      0.1059694000
_diffrn_orient_matrix_UB_32      -0.0039010000
_diffrn_orient_matrix_UB_33      -0.0074444000
_diffrn_oxdiff_ac4_digest_frames 
;
0125fe93a30c1f432f0de031e1e462cf44000283f23
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2484
_reflns_number_total             3039
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.0380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0715
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8532(4) 0.4569(2) 0.51159(15) 0.0488(8) Uani 1 1 d . . . . .
C2 C 0.8599(6) 0.5176(3) 0.4526(2) 0.0359(9) Uani 1 1 d . . . . .
N3 N 0.7165(5) 0.5110(3) 0.40444(17) 0.0354(8) Uani 1 1 d . . . . .
N4 N 0.5854(5) 0.4313(2) 0.43170(16) 0.0347(7) Uani 1 1 d . . . . .
B5 B 0.6631(8) 0.3917(4) 0.5090(3) 0.0448(13) Uani 1 1 d . . . . .
C6 C 1.0335(6) 0.5896(3) 0.4448(2) 0.0365(9) Uani 1 1 d . . . . .
S7 S 1.04962(16) 0.67520(9) 0.37058(5) 0.0441(3) Uani 1 1 d . . . . .
C8 C 1.2830(7) 0.7196(4) 0.4005(2) 0.0458(11) Uani 1 1 d . . . . .
C9 C 1.3426(6) 0.6733(3) 0.4634(2) 0.0442(10) Uani 1 1 d . . . . .
H9 H 1.464184 0.689092 0.487266 0.053 Uiso 1 1 calc R U . . .
C10 C 1.1993(6) 0.5983(3) 0.4884(2) 0.0401(10) Uani 1 1 d . . . . .
H10 H 1.216365 0.558349 0.530964 0.048 Uiso 1 1 calc R U . . .
Br11 Br 1.43168(9) 0.81841(4) 0.34480(3) 0.0740(2) Uani 1 1 d . . . . .
C12 C 0.4247(6) 0.4017(3) 0.3949(2) 0.0352(9) Uani 1 1 d . . . . .
H12 H 0.344075 0.349004 0.416716 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3575(5) 0.4390(3) 0.3265(2) 0.0349(9) Uani 1 1 d . . . . .
N14 N 0.4517(5) 0.5197(3) 0.28633(17) 0.0363(8) Uani 1 1 d . . . . .
C15 C 0.3451(6) 0.5396(3) 0.2251(2) 0.0414(10) Uani 1 1 d . . . . .
C16 C 0.1774(7) 0.4712(4) 0.2250(2) 0.0462(11) Uani 1 1 d . . . . .
H16 H 0.077722 0.467983 0.188916 0.055 Uiso 1 1 calc R U . . .
C17 C 0.1831(6) 0.4080(3) 0.2881(2) 0.0413(10) Uani 1 1 d . . . . .
C18 C 0.4122(7) 0.6233(4) 0.1713(2) 0.0571(12) Uani 1 1 d . . . . .
H18A H 0.399494 0.693567 0.192881 0.086 Uiso 1 1 calc R U . . .
H18B H 0.328142 0.619359 0.128399 0.086 Uiso 1 1 calc R U . . .
H18C H 0.551924 0.610791 0.158074 0.086 Uiso 1 1 calc R U . . .
C19 C 0.0331(6) 0.3224(3) 0.3105(2) 0.0554(12) Uani 1 1 d . . . . .
H19A H 0.075041 0.254116 0.290830 0.083 Uiso 1 1 calc R U . . .
H19B H -0.099770 0.340368 0.292124 0.083 Uiso 1 1 calc R U . . .
H19C H 0.028410 0.317995 0.362854 0.083 Uiso 1 1 calc R U . . .
F20 F 0.5312(4) 0.4198(2) 0.56345(13) 0.0708(8) Uani 1 1 d . . . . .
F21 F 0.7020(4) 0.2837(2) 0.50865(17) 0.0676(8) Uani 1 1 d . . . . .
H14 H 0.559(6) 0.552(3) 0.300(2) 0.035(11) Uiso 1 1 d . . . . .


_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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.317(5) . ?
O1 B5 1.486(6) . ?
C2 N3 1.291(5) . ?
C2 C6 1.454(5) . ?
N3 N4 1.402(4) . ?
N4 B5 1.581(5) . ?
N4 C12 1.303(5) . ?
B5 F20 1.365(6) . ?
B5 F21 1.363(6) . ?
C6 S7 1.727(4) . ?
C6 C10 1.353(5) . ?
S7 C8 1.716(4) . ?
C8 C9 1.344(6) . ?
C8 Br11 1.868(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.399(5) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.405(5) . ?
C13 N14 1.387(5) . ?
C13 C17 1.396(5) . ?
N14 C15 1.343(5) . ?
N14 H14 0.84(4) . ?
C15 C16 1.389(6) . ?
C15 C18 1.497(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.394(6) . ?
C17 C19 1.504(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C2 O1 B5 108.2(3) . . ?
O1 C2 C6 117.3(3) . . ?
N3 C2 O1 120.0(4) . . ?
N3 C2 C6 122.8(4) . . ?
C2 N3 N4 104.3(3) . . ?
N3 N4 B5 109.9(3) . . ?
C12 N4 N3 120.7(3) . . ?
C12 N4 B5 129.4(3) . . ?
O1 B5 N4 97.5(3) . . ?
F20 B5 O1 111.6(4) . . ?
F20 B5 N4 111.7(4) . . ?
F21 B5 O1 112.2(4) . . ?
F21 B5 N4 111.2(4) . . ?
F21 B5 F20 111.9(4) . . ?
C2 C6 S7 120.2(3) . . ?
C10 C6 C2 128.3(4) . . ?
C10 C6 S7 111.4(3) . . ?
C8 S7 C6 90.1(2) . . ?
S7 C8 Br11 120.1(3) . . ?
C9 C8 S7 113.3(3) . . ?
C9 C8 Br11 126.6(3) . . ?
C8 C9 H9 124.2 . . ?
C8 C9 C10 111.7(4) . . ?
C10 C9 H9 124.2 . . ?
C6 C10 C9 113.6(4) . . ?
C6 C10 H10 123.2 . . ?
C9 C10 H10 123.2 . . ?
N4 C12 H12 115.8 . . ?
N4 C12 C13 128.4(4) . . ?
C13 C12 H12 115.8 . . ?
N14 C13 C12 124.8(3) . . ?
N14 C13 C17 107.2(3) . . ?
C17 C13 C12 127.9(4) . . ?
C13 N14 H14 123(3) . . ?
C15 N14 C13 110.0(3) . . ?
C15 N14 H14 127(3) . . ?
N14 C15 C16 107.5(4) . . ?
N14 C15 C18 121.5(4) . . ?
C16 C15 C18 131.0(4) . . ?
C15 C16 H16 125.6 . . ?
C15 C16 C17 108.7(4) . . ?
C17 C16 H16 125.6 . . ?
C13 C17 C19 126.3(4) . . ?
C16 C17 C13 106.5(4) . . ?
C16 C17 C19 127.2(4) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O1 C2 N3 N4 -1.3(5) . . . . ?
O1 C2 C6 S7 -177.8(3) . . . . ?
O1 C2 C6 C10 4.7(6) . . . . ?
C2 O1 B5 N4 2.9(4) . . . . ?
C2 O1 B5 F20 -114.0(4) . . . . ?
C2 O1 B5 F21 119.5(4) . . . . ?
C2 N3 N4 B5 3.3(4) . . . . ?
C2 N3 N4 C12 -178.0(3) . . . . ?
C2 C6 S7 C8 -177.3(3) . . . . ?
C2 C6 C10 C9 177.5(4) . . . . ?
N3 C2 C6 S7 2.6(5) . . . . ?
N3 C2 C6 C10 -174.9(4) . . . . ?
N3 N4 B5 O1 -3.8(4) . . . . ?
N3 N4 B5 F20 113.1(4) . . . . ?
N3 N4 B5 F21 -121.2(4) . . . . ?
N3 N4 C12 C13 0.7(6) . . . . ?
N4 C12 C13 N14 -2.4(6) . . . . ?
N4 C12 C13 C17 -178.8(4) . . . . ?
B5 O1 C2 N3 -1.4(5) . . . . ?
B5 O1 C2 C6 179.0(4) . . . . ?
B5 N4 C12 C13 179.3(4) . . . . ?
C6 C2 N3 N4 178.3(3) . . . . ?
C6 S7 C8 C9 -0.8(3) . . . . ?
C6 S7 C8 Br11 176.7(3) . . . . ?
S7 C6 C10 C9 -0.1(4) . . . . ?
S7 C8 C9 C10 0.9(5) . . . . ?
C8 C9 C10 C6 -0.5(5) . . . . ?
C10 C6 S7 C8 0.5(3) . . . . ?
Br11 C8 C9 C10 -176.4(3) . . . . ?
C12 N4 B5 O1 177.6(4) . . . . ?
C12 N4 B5 F20 -65.6(5) . . . . ?
C12 N4 B5 F21 60.2(6) . . . . ?
C12 C13 N14 C15 -177.4(4) . . . . ?
C12 C13 C17 C16 177.2(4) . . . . ?
C12 C13 C17 C19 -3.4(6) . . . . ?
C13 N14 C15 C16 0.3(4) . . . . ?
C13 N14 C15 C18 -180.0(4) . . . . ?
N14 C13 C17 C16 0.3(4) . . . . ?
N14 C13 C17 C19 179.7(4) . . . . ?
N14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C13 -0.1(5) . . . . ?
C15 C16 C17 C19 -179.5(4) . . . . ?
C17 C13 N14 C15 -0.4(4) . . . . ?
C18 C15 C16 C17 -179.8(4) . . . . ?

_olex2_date_sample_data_collection 2022-03-17
_olex2_date_sample_submission    2022-03-17
_olex2_submission_original_sample_id JK048
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.796
####################################################################### 
# 
# 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_wdh1118
_database_code_depnum_ccdc_archive 'CCDC 2277472'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2022-08-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
luc.vanmeervelt@kuleuven.be
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 B F2 N3 O'
_chemical_formula_sum            'C9 H12 B F2 N3 O'
_chemical_formula_weight         227.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H12N3O1F2B1
_chemical_oxdiff_usercomment     'Jonathan - 2a'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.4328(6)
_cell_length_b                   8.6941(6)
_cell_length_c                   9.1341(6)
_cell_angle_alpha                69.030(6)
_cell_angle_beta                 74.586(6)
_cell_angle_gamma                63.527(7)
_cell_volume                     555.21(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3335
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2350
_cell_measurement_theta_min      2.9890
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11486
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.407
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    2.50    --  -17.15 -99.00 120.00   45
  2  ω    -20.00  25.00   1.00    2.50    --  -17.15 -99.00 -30.00   45
  3  ω    -50.00  40.00   1.00    2.50    --   18.87 -57.00-150.00   90
  4  ω     35.00  95.00   1.00    2.50    --   18.87 178.00-150.00   60
  5  ω     -7.00  91.00   1.00    2.50    --   18.87  38.00   0.00   98
  6  ω    -50.00  40.00   1.00    2.50    --   18.87 -57.00  30.00   90
  7  ω    -54.00  44.00   1.00    2.50    --   18.87 -38.00-180.00   98
  8  ω    -86.00   4.00   1.00    2.50    --  -17.15 -57.00-180.00   90
  9  ω    -86.00   4.00   1.00    2.50    --  -17.15 -57.00  60.00   90
 10  ω    -39.00  52.00   1.00    2.50    --  -17.15  57.00 -30.00   91
 11  ω     11.00  86.00   1.00    2.50    --   18.87-140.00  24.00   75
 12  ω      5.00  79.00   1.00    2.50    --   18.87-129.00-162.00   74
 13  ω     -3.00  88.00   1.00    2.50    --   18.87  57.00-120.00   91
 14  ω    -86.00 -59.00   1.00    2.50    --  -17.15 -57.00   0.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0459539000
_diffrn_orient_matrix_UB_12      -0.0574933000
_diffrn_orient_matrix_UB_13      -0.0497824000
_diffrn_orient_matrix_UB_21      -0.0226963000
_diffrn_orient_matrix_UB_22      0.0747210000
_diffrn_orient_matrix_UB_23      -0.0673894000
_diffrn_orient_matrix_UB_31      0.0796714000
_diffrn_orient_matrix_UB_32      0.0105088000
_diffrn_orient_matrix_UB_33      -0.0031572000
_diffrn_oxdiff_ac4_digest_frames 
;
01e4c0521df76f252f4c2e436cb229b2dd0002804e8
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1636
_reflns_number_total             2274
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.2528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1411
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4012(2) 0.6007(2) 0.80276(18) 0.0599(5) Uani 1 1 d . . . . .
B2 B 0.4369(4) 0.7497(4) 0.6786(3) 0.0528(6) Uani 1 1 d . . . . .
N3 N 0.5999(2) 0.6377(2) 0.5784(2) 0.0465(4) Uani 1 1 d . . . . .
N4 N 0.6241(2) 0.4558(2) 0.6381(2) 0.0496(5) Uani 1 1 d . . . . .
C5 C 0.5080(3) 0.4494(3) 0.7643(3) 0.0506(5) Uani 1 1 d . . . . .
F6 F 0.29562(18) 0.8591(2) 0.59213(17) 0.0723(5) Uani 1 1 d . . . . .
F7 F 0.4800(2) 0.8502(2) 0.73705(18) 0.0723(5) Uani 1 1 d . . . . .
C8 C 0.7075(3) 0.6883(3) 0.4591(2) 0.0458(5) Uani 1 1 d . . . . .
H8 H 0.688458 0.808554 0.430740 0.055 Uiso 1 1 calc R U . . .
C9 C 0.8481(3) 0.5862(3) 0.3676(2) 0.0445(5) Uani 1 1 d . . . . .
N10 N 0.8928(2) 0.4080(3) 0.3826(2) 0.0466(5) Uani 1 1 d . . . . .
C11 C 1.0282(3) 0.3542(3) 0.2698(3) 0.0491(5) Uani 1 1 d . . . . .
C12 C 1.0735(3) 0.4988(3) 0.1814(3) 0.0540(6) Uani 1 1 d . . . . .
H12 H 1.163690 0.498411 0.096559 0.065 Uiso 1 1 calc R U . . .
C13 C 0.9627(3) 0.6442(3) 0.2397(3) 0.0491(5) Uani 1 1 d . . . . .
C14 C 1.1043(4) 0.1692(3) 0.2541(3) 0.0673(7) Uani 1 1 d . . . . .
H14A H 1.156572 0.085901 0.347686 0.101 Uiso 1 1 calc R U . . .
H14B H 1.194389 0.159974 0.163966 0.101 Uiso 1 1 calc R U . . .
H14C H 1.011243 0.142394 0.240553 0.101 Uiso 1 1 calc R U . . .
C15 C 0.9667(4) 0.8270(3) 0.1802(3) 0.0707(7) Uani 1 1 d . . . . .
H15A H 0.854187 0.913158 0.144792 0.106 Uiso 1 1 calc R U . . .
H15B H 1.060561 0.829645 0.093762 0.106 Uiso 1 1 calc R U . . .
H15C H 0.987763 0.855319 0.263783 0.106 Uiso 1 1 calc R U . . .
C16 C 0.4909(4) 0.2813(4) 0.8671(3) 0.0667(7) Uani 1 1 d . . . . .
H16A H 0.522054 0.255870 0.969394 0.100 Uiso 1 1 calc R U . . .
H16B H 0.569536 0.185345 0.821127 0.100 Uiso 1 1 calc R U . . .
H16C H 0.369901 0.293143 0.877777 0.100 Uiso 1 1 calc R U . . .
H10 H 0.840(3) 0.346(4) 0.450(3) 0.067(8) Uiso 1 1 d . . . . .


_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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B2 1.473(3) . ?
O1 C5 1.331(3) . ?
B2 N3 1.565(3) . ?
B2 F6 1.378(3) . ?
B2 F7 1.379(3) . ?
N3 N4 1.412(2) . ?
N3 C8 1.301(3) . ?
N4 C5 1.301(3) . ?
C5 C16 1.474(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.399(3) . ?
C9 N10 1.384(3) . ?
C9 C13 1.402(3) . ?
N10 C11 1.351(3) . ?
N10 H10 0.83(3) . ?
C11 C12 1.385(3) . ?
C11 C14 1.488(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 C15 1.497(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C5 O1 B2 108.42(17) . . ?
O1 B2 N3 98.41(18) . . ?
F6 B2 O1 111.8(2) . . ?
F6 B2 N3 111.10(19) . . ?
F6 B2 F7 109.8(2) . . ?
F7 B2 O1 112.8(2) . . ?
F7 B2 N3 112.5(2) . . ?
N4 N3 B2 109.58(17) . . ?
C8 N3 B2 130.00(19) . . ?
C8 N3 N4 120.40(18) . . ?
C5 N4 N3 104.48(18) . . ?
O1 C5 C16 118.7(2) . . ?
N4 C5 O1 118.6(2) . . ?
N4 C5 C16 122.7(2) . . ?
N3 C8 H8 115.6 . . ?
N3 C8 C9 128.7(2) . . ?
C9 C8 H8 115.6 . . ?
C8 C9 C13 127.6(2) . . ?
N10 C9 C8 125.30(19) . . ?
N10 C9 C13 107.06(18) . . ?
C9 N10 H10 123.8(18) . . ?
C11 N10 C9 109.81(19) . . ?
C11 N10 H10 126.4(18) . . ?
N10 C11 C12 107.5(2) . . ?
N10 C11 C14 122.4(2) . . ?
C12 C11 C14 130.1(2) . . ?
C11 C12 H12 125.5 . . ?
C11 C12 C13 108.9(2) . . ?
C13 C12 H12 125.5 . . ?
C9 C13 C15 126.5(2) . . ?
C12 C13 C9 106.71(19) . . ?
C12 C13 C15 126.8(2) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O1 B2 N3 N4 6.8(2) . . . . ?
O1 B2 N3 C8 -172.0(2) . . . . ?
B2 O1 C5 N4 3.5(3) . . . . ?
B2 O1 C5 C16 -177.0(2) . . . . ?
B2 N3 N4 C5 -5.2(2) . . . . ?
B2 N3 C8 C9 -177.2(2) . . . . ?
N3 N4 C5 O1 1.2(3) . . . . ?
N3 N4 C5 C16 -178.3(2) . . . . ?
N3 C8 C9 N10 4.2(4) . . . . ?
N3 C8 C9 C13 -179.7(2) . . . . ?
N4 N3 C8 C9 4.2(3) . . . . ?
C5 O1 B2 N3 -5.9(2) . . . . ?
C5 O1 B2 F6 110.9(2) . . . . ?
C5 O1 B2 F7 -124.7(2) . . . . ?
F6 B2 N3 N4 -110.5(2) . . . . ?
F6 B2 N3 C8 70.7(3) . . . . ?
F7 B2 N3 N4 125.9(2) . . . . ?
F7 B2 N3 C8 -52.9(3) . . . . ?
C8 N3 N4 C5 173.68(19) . . . . ?
C8 C9 N10 C11 176.4(2) . . . . ?
C8 C9 C13 C12 -176.7(2) . . . . ?
C8 C9 C13 C15 4.4(4) . . . . ?
C9 N10 C11 C12 0.6(2) . . . . ?
C9 N10 C11 C14 -179.2(2) . . . . ?
N10 C9 C13 C12 -0.1(2) . . . . ?
N10 C9 C13 C15 -179.0(2) . . . . ?
N10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C9 0.5(3) . . . . ?
C11 C12 C13 C15 179.4(2) . . . . ?
C13 C9 N10 C11 -0.4(2) . . . . ?
C14 C11 C12 C13 179.2(2) . . . . ?

_olex2_date_sample_submission    2022-08-29
_olex2_submission_original_sample_id 2a
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.540
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# 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_wdh1115-2
_database_code_depnum_ccdc_archive 'CCDC 2277476'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2022-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
luc.vanmeervelt@kuleuven.be
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 B F2 N3 O S'
_chemical_formula_sum            'C24 H24 B F2 N3 O S'
_chemical_formula_weight         451.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H23 N3 B1 O1 F2 S1'
_chemical_oxdiff_usercomment     'JK285-NMR tube'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.6651(3)
_cell_length_b                   9.2403(3)
_cell_length_c                   32.1446(10)
_cell_angle_alpha                86.941(2)
_cell_angle_beta                 89.022(3)
_cell_angle_gamma                65.310(3)
_cell_volume                     2335.10(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9980
_cell_measurement_theta_min      2.6970
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            47736
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.479
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  53.00   1.00   15.00    --  -17.07  77.00  60.00  100
  2  ω    -47.00  53.00   1.00   15.00    --  -17.07  77.00  90.00  100
  3  ω    -47.00  53.00   1.00   15.00    --  -17.07  77.00 -30.00  100
  4  ω    -47.00  53.00   1.00   15.00    --  -17.07  77.00-180.00  100
  5  ω    -11.00  89.00   1.00   15.00    --   18.87  77.00 -60.00  100
  6  ω    -11.00  89.00   1.00   15.00    --   18.87  77.00-180.00  100
  7  ω    -93.00 -35.00   1.00   15.00    --  -17.07-178.00 150.00   58
  8  ω    -20.00  25.00   1.00   15.00    --  -17.07 -99.00 -30.00   45
  9  ω    -20.00  61.00   1.00   15.00    --   18.87 -99.00 -60.00   81
 10  ω    -50.00  40.00   1.00   15.00    --   18.87 -57.00 -60.00   90
 11  ω     -3.00  88.00   1.00   15.00    --   18.87  57.00  90.00   91
 12  ω    -20.00  41.00   1.00   15.00    --   18.87 -99.00 150.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0329031000
_diffrn_orient_matrix_UB_12      -0.0766367000
_diffrn_orient_matrix_UB_13      -0.0083136000
_diffrn_orient_matrix_UB_21      0.0135677000
_diffrn_orient_matrix_UB_22      -0.0357567000
_diffrn_orient_matrix_UB_23      0.0204741000
_diffrn_orient_matrix_UB_31      -0.0827673000
_diffrn_orient_matrix_UB_32      0.0021128000
_diffrn_orient_matrix_UB_33      -0.0000873000
_diffrn_oxdiff_ac4_digest_frames 
;
01db2c4114d314229ca51b1da54753c1e900027aba9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6267
_reflns_number_total             9539
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     620
_refine_ls_number_reflns         9539
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+2.0947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1527
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C51-C52A = C51-C52B
 1.522 with sigma of 0.01
 C52A-C53A = C52B-C53B
 1.505 with sigma of 0.01
 C53A-C54A = C53B-C54B
 1.508 with sigma of 0.01
3. Others
 Sof(H51C)=Sof(H51D)=Sof(C52B)=Sof(H52C)=Sof(H52D)=Sof(C53B)=Sof(H53C)=
 Sof(H53D)=Sof(C54B)=Sof(H54D)=Sof(H54E)=Sof(H54F)=1-FVAR(1)
 Sof(H51A)=Sof(H51B)=Sof(C52A)=Sof(H52A)=Sof(H52B)=Sof(C53A)=Sof(H53A)=
 Sof(H53B)=Sof(C54A)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C51(H51A,H51B), C51(H51C,
 H51D), C52A(H52A,H52B), C53A(H53A,H53B), C52B(H52C,H52D), C53B(H53C,H53D)
4.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C14(H14), C15(H15), C17(H17), C18(H18), C23(H23), C27(H27),
 C41(H41), C42(H42), C46(H46), C47(H47), C49(H49), C50(H50), C55(H55), C59(H59)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C54A(H54A,H54B,
 H54C), C54B(H54D,H54E,H54F), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0977(3) 1.7350(2) 0.42514(6) 0.0548(5) Uani 1 1 d . . . . .
C2 C 0.0052(3) 1.5815(3) 0.43191(9) 0.0449(6) Uani 1 1 d . . . . .
N3 N 0.1144(3) 1.5395(3) 0.46246(7) 0.0471(6) Uani 1 1 d . . . . .
N4 N 0.0885(3) 1.6833(3) 0.47999(7) 0.0479(6) Uani 1 1 d . . . . .
B5 B -0.0623(5) 1.8252(4) 0.45765(12) 0.0580(9) Uani 1 1 d . . . . .
C6 C -0.0078(4) 1.4699(3) 0.40424(9) 0.0470(7) Uani 1 1 d . . . . .
S7 S 0.13526(11) 1.27355(10) 0.40594(3) 0.0590(2) Uani 1 1 d . . . . .
C8 C 0.0358(4) 1.2341(4) 0.36457(9) 0.0568(8) Uani 1 1 d . . . . .
C9 C -0.1015(4) 1.3671(4) 0.35136(10) 0.0616(8) Uani 1 1 d . . . . .
H9 H -0.171814 1.368934 0.329613 0.074 Uiso 1 1 calc R U . . .
C10 C -0.1267(4) 1.5016(4) 0.37379(9) 0.0548(8) Uani 1 1 d . . . . .
H10 H -0.215026 1.601465 0.368427 0.066 Uiso 1 1 calc R U . . .
C11 C 0.1041(5) 1.0789(4) 0.34879(10) 0.0649(9) Uani 1 1 d . . . . .
C12 C 0.1639(5) 0.9494(4) 0.33544(11) 0.0677(9) Uani 1 1 d . . . . .
C13 C 0.2324(5) 0.7922(4) 0.31965(10) 0.0625(9) Uani 1 1 d . . . . .
C14 C 0.1628(4) 0.6868(4) 0.33058(10) 0.0610(8) Uani 1 1 d . . . . .
H14 H 0.071935 0.716352 0.348943 0.073 Uiso 1 1 calc R U . . .
C15 C 0.2264(4) 0.5376(4) 0.31461(11) 0.0659(9) Uani 1 1 d . . . . .
H15 H 0.177478 0.467974 0.322481 0.079 Uiso 1 1 calc R U . . .
C16 C 0.3600(5) 0.4894(4) 0.28738(11) 0.0690(9) Uani 1 1 d . . . . .
C17 C 0.4347(6) 0.5929(5) 0.27783(15) 0.1068(16) Uani 1 1 d . . . . .
H17 H 0.529195 0.560994 0.260582 0.128 Uiso 1 1 calc R U . . .
C18 C 0.3722(6) 0.7409(5) 0.29328(15) 0.1071(16) Uani 1 1 d . . . . .
H18 H 0.423749 0.809004 0.286076 0.129 Uiso 1 1 calc R U . . .
C19 C 0.4286(6) 0.3248(5) 0.26968(13) 0.0896(12) Uani 1 1 d . . . . .
H19A H 0.334404 0.304740 0.259915 0.107 Uiso 1 1 calc R U . . .
H19B H 0.500101 0.322627 0.245945 0.107 Uiso 1 1 calc R U . . .
C20 C 0.5301(7) 0.1944(5) 0.30134(16) 0.1114(16) Uani 1 1 d . . . . .
H20A H 0.620482 0.218132 0.312042 0.134 Uiso 1 1 calc R U . . .
H20B H 0.456690 0.194538 0.324476 0.134 Uiso 1 1 calc R U . . .
C21 C 0.6049(8) 0.0348(6) 0.28511(19) 0.135(2) Uani 1 1 d . . . . .
H21A H 0.686491 0.030036 0.263591 0.162 Uiso 1 1 calc R U . . .
H21B H 0.516716 0.011667 0.272825 0.162 Uiso 1 1 calc R U . . .
C22 C 0.6918(9) -0.0870(8) 0.3199(2) 0.200(4) Uani 1 1 d . . . . .
H22A H 0.752735 -0.047119 0.337269 0.300 Uiso 1 1 calc R U . . .
H22B H 0.769793 -0.184209 0.308312 0.300 Uiso 1 1 calc R U . . .
H22C H 0.608373 -0.107177 0.336155 0.300 Uiso 1 1 calc R U . . .
C23 C 0.1852(4) 1.6861(4) 0.51039(9) 0.0486(7) Uani 1 1 d . . . . .
H23 H 0.164683 1.786983 0.519046 0.058 Uiso 1 1 calc R U . . .
C24 C 0.3144(3) 1.5596(4) 0.53165(8) 0.0468(7) Uani 1 1 d . . . . .
N25 N 0.3585(3) 1.3990(3) 0.52620(8) 0.0503(6) Uani 1 1 d . . . . .
H25 H 0.311(4) 1.364(3) 0.5072(9) 0.058(9) Uiso 1 1 d . . . . .
C26 C 0.4837(4) 1.3089(4) 0.55308(10) 0.0571(8) Uani 1 1 d . . . . .
C27 C 0.5226(4) 1.4122(4) 0.57597(10) 0.0646(9) Uani 1 1 d . . . . .
H27 H 0.605308 1.381531 0.596713 0.078 Uiso 1 1 calc R U . . .
C28 C 0.4196(4) 1.5682(4) 0.56324(9) 0.0564(8) Uani 1 1 d . . . . .
C29 C 0.5572(5) 1.1315(4) 0.55503(13) 0.0809(11) Uani 1 1 d . . . . .
H29A H 0.663317 1.090025 0.569891 0.121 Uiso 1 1 calc R U . . .
H29B H 0.575784 1.094293 0.527281 0.121 Uiso 1 1 calc R U . . .
H29C H 0.479943 1.095874 0.569179 0.121 Uiso 1 1 calc R U . . .
C30 C 0.4184(5) 1.7170(4) 0.57950(12) 0.0771(11) Uani 1 1 d . . . . .
H30A H 0.446435 1.775890 0.557444 0.116 Uiso 1 1 calc R U . . .
H30B H 0.500499 1.689644 0.601581 0.116 Uiso 1 1 calc R U . . .
H30C H 0.307501 1.781062 0.589949 0.116 Uiso 1 1 calc R U . . .
F31 F -0.0166(3) 1.9409(2) 0.44153(7) 0.0904(7) Uani 1 1 d . . . . .
F32 F -0.1992(2) 1.8881(3) 0.48363(6) 0.0920(7) Uani 1 1 d . . . . .
O33 O 0.4068(3) 0.7055(2) 0.07536(6) 0.0561(5) Uani 1 1 d . . . . .
C34 C 0.5078(4) 0.5542(3) 0.06860(8) 0.0470(7) Uani 1 1 d . . . . .
N35 N 0.6156(3) 0.5225(3) 0.03815(7) 0.0483(6) Uani 1 1 d . . . . .
N36 N 0.5901(3) 0.6732(3) 0.02049(7) 0.0481(6) Uani 1 1 d . . . . .
B37 B 0.4408(5) 0.8073(5) 0.04265(12) 0.0618(10) Uani 1 1 d . . . . .
C38 C 0.4948(4) 0.4326(4) 0.09651(9) 0.0502(7) Uani 1 1 d . . . . .
S39 S 0.63638(11) 0.23640(10) 0.09513(3) 0.0627(2) Uani 1 1 d . . . . .
C40 C 0.5383(5) 0.1839(4) 0.13659(10) 0.0627(9) Uani 1 1 d . . . . .
C41 C 0.4022(5) 0.3132(5) 0.14977(10) 0.0683(9) Uani 1 1 d . . . . .
H41 H 0.332663 0.307813 0.171601 0.082 Uiso 1 1 calc R U . . .
C42 C 0.3776(4) 0.4547(4) 0.12723(9) 0.0598(8) Uani 1 1 d . . . . .
H42 H 0.290780 0.553240 0.132571 0.072 Uiso 1 1 calc R U . . .
C43 C 0.6054(5) 0.0223(5) 0.15311(11) 0.0714(10) Uani 1 1 d . . . . .
C44 C 0.6651(5) -0.1116(5) 0.16709(11) 0.0736(10) Uani 1 1 d . . . . .
C45 C 0.7346(5) -0.2736(4) 0.18380(10) 0.0664(9) Uani 1 1 d . . . . .
C46 C 0.8615(6) -0.3270(5) 0.21395(15) 0.1030(15) Uani 1 1 d . . . . .
H46 H 0.902403 -0.256787 0.223812 0.124 Uiso 1 1 calc R U . . .
C47 C 0.9274(6) -0.4826(5) 0.22940(14) 0.0991(14) Uani 1 1 d . . . . .
H47 H 1.013160 -0.515782 0.249413 0.119 Uiso 1 1 calc R U . . .
C48 C 0.8706(5) -0.5904(4) 0.21622(11) 0.0690(9) Uani 1 1 d . . . . .
C49 C 0.7441(5) -0.5357(4) 0.18608(11) 0.0694(9) Uani 1 1 d . . . . .
H49 H 0.703056 -0.606046 0.176406 0.083 Uiso 1 1 calc R U . . .
C50 C 0.6774(4) -0.3813(4) 0.17002(10) 0.0653(9) Uani 1 1 d . . . . .
H50 H 0.592993 -0.348973 0.149685 0.078 Uiso 1 1 calc R U . . .
C51 C 0.9408(6) -0.7579(5) 0.23471(15) 0.1038(15) Uani 1 1 d D . . . .
H51A H 1.047838 -0.774766 0.247576 0.125 Uiso 0.464(11) 1 calc R U P A 1
H51B H 0.865186 -0.756772 0.257411 0.125 Uiso 0.464(11) 1 calc R U P A 1
H51C H 0.849388 -0.784717 0.244803 0.125 Uiso 0.536(11) 1 calc R U P A 2
H51D H 1.016112 -0.769440 0.257859 0.125 Uiso 0.536(11) 1 calc R U P A 2
C52A C 0.9752(15) -0.9066(12) 0.2130(4) 0.107(4) Uani 0.464(11) 1 d D . P A 1
H52A H 0.994935 -0.995378 0.232870 0.128 Uiso 0.464(11) 1 calc R U P A 1
H52B H 0.880983 -0.892917 0.194949 0.128 Uiso 0.464(11) 1 calc R U P A 1
C53A C 1.1303(17) -0.9327(15) 0.1884(4) 0.128(6) Uani 0.464(11) 1 d D . P A 1
H53A H 1.223174 -0.947999 0.207095 0.153 Uiso 0.464(11) 1 calc R U P A 1
H53B H 1.110088 -0.839418 0.170170 0.153 Uiso 0.464(11) 1 calc R U P A 1
C54A C 1.178(4) -1.0770(17) 0.1628(6) 0.158(8) Uani 0.464(11) 1 d D . P A 1
H54A H 1.249379 -1.170757 0.179038 0.237 Uiso 0.464(11) 1 calc R U P A 1
H54B H 1.237620 -1.065111 0.138369 0.237 Uiso 0.464(11) 1 calc R U P A 1
H54C H 1.076769 -1.087003 0.154675 0.237 Uiso 0.464(11) 1 calc R U P A 1
C52B C 1.0384(17) -0.8673(9) 0.2002(3) 0.111(4) Uani 0.536(11) 1 d D . P A 2
H52C H 0.960962 -0.849716 0.177090 0.134 Uiso 0.536(11) 1 calc R U P A 2
H52D H 1.126901 -0.835972 0.190347 0.134 Uiso 0.536(11) 1 calc R U P A 2
C53B C 1.1181(16) -1.0415(10) 0.2119(3) 0.139(5) Uani 0.536(11) 1 d D . P A 2
H53C H 1.207890 -1.060591 0.231947 0.167 Uiso 0.536(11) 1 calc R U P A 2
H53D H 1.033117 -1.068491 0.226092 0.167 Uiso 0.536(11) 1 calc R U P A 2
C54B C 1.191(3) -1.1537(17) 0.1779(5) 0.176(9) Uani 0.536(11) 1 d D . P A 2
H54D H 1.107146 -1.131086 0.156513 0.264 Uiso 0.536(11) 1 calc R U P A 2
H54E H 1.225433 -1.261341 0.188939 0.264 Uiso 0.536(11) 1 calc R U P A 2
H54F H 1.287988 -1.141096 0.166388 0.264 Uiso 0.536(11) 1 calc R U P A 2
C55 C 0.6853(4) 0.6873(4) -0.01001(9) 0.0498(7) Uani 1 1 d . . . . .
H55 H 0.664453 0.791415 -0.018762 0.060 Uiso 1 1 calc R U . . .
C56 C 0.8136(4) 0.5688(4) -0.03128(9) 0.0484(7) Uani 1 1 d . . . . .
N57 N 0.8572(3) 0.4057(3) -0.02578(8) 0.0505(6) Uani 1 1 d . . . . .
H57 H 0.812(4) 0.366(3) -0.0069(9) 0.052(9) Uiso 1 1 d . . . . .
C58 C 0.9816(4) 0.3266(4) -0.05274(10) 0.0589(8) Uani 1 1 d . . . . .
C59 C 1.0205(4) 0.4380(4) -0.07540(10) 0.0648(9) Uani 1 1 d . . . . .
H59 H 1.102645 0.415375 -0.096035 0.078 Uiso 1 1 calc R U . . .
C60 C 0.9181(4) 0.5886(4) -0.06257(9) 0.0555(8) Uani 1 1 d . . . . .
C61 C 1.0528(5) 0.1500(4) -0.05471(12) 0.0821(11) Uani 1 1 d . . . . .
H61A H 1.088541 0.101252 -0.027373 0.123 Uiso 1 1 calc R U . . .
H61B H 1.148368 0.114759 -0.073146 0.123 Uiso 1 1 calc R U . . .
H61C H 0.967316 0.119993 -0.064901 0.123 Uiso 1 1 calc R U . . .
C62 C 0.9171(5) 0.7440(5) -0.07859(12) 0.0799(11) Uani 1 1 d . . . . .
H62A H 0.804405 0.814852 -0.087630 0.120 Uiso 1 1 calc R U . . .
H62B H 0.993778 0.726071 -0.101624 0.120 Uiso 1 1 calc R U . . .
H62C H 0.952388 0.790813 -0.056801 0.120 Uiso 1 1 calc R U . . .
F63 F 0.3027(3) 0.8800(3) 0.01661(7) 0.0962(8) Uani 1 1 d . . . . .
F64 F 0.4884(3) 0.9166(2) 0.05863(7) 0.0948(7) Uani 1 1 d . . . . .


_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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.331(3) . ?
O1 B5 1.483(4) . ?
C52Aa H52A 0.9700 . ?
C52Aa H52B 0.9700 . ?
C52Aa C53A 1.484(9) . ?
C53Aa H53A 0.9700 . ?
C53Aa H53B 0.9700 . ?
C53Aa C54A 1.508(9) . ?
C54Aa H54A 0.9600 . ?
C54Aa H54B 0.9600 . ?
C54Aa H54C 0.9600 . ?
C52Bb H52C 0.9700 . ?
C52Bb H52D 0.9700 . ?
C52Bb C53B 1.491(8) . ?
C53Bb H53C 0.9700 . ?
C53Bb H53D 0.9700 . ?
C53Bb C54B 1.491(9) . ?
C54Bb H54D 0.9600 . ?
C54Bb H54E 0.9600 . ?
C54Bb H54F 0.9600 . ?
C2 N3 1.302(3) . ?
C2 C6 1.437(4) . ?
N3 N4 1.400(3) . ?
N4 B5 1.563(4) . ?
N4 C23 1.306(3) . ?
B5 F31 1.362(4) . ?
B5 F32 1.373(4) . ?
C6 S7 1.716(3) . ?
C6 C10 1.363(4) . ?
S7 C8 1.731(3) . ?
C8 C9 1.359(4) . ?
C8 C11 1.422(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.406(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.189(4) . ?
C12 C13 1.438(5) . ?
C13 C14 1.372(4) . ?
C13 C18 1.392(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(5) . ?
C16 C17 1.381(5) . ?
C16 C19 1.522(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.362(5) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.509(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.462(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.506(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.391(4) . ?
C24 N25 1.390(4) . ?
C24 C28 1.403(4) . ?
N25 H25 0.89(3) . ?
N25 C26 1.348(4) . ?
C26 C27 1.386(5) . ?
C26 C29 1.488(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.385(5) . ?
C28 C30 1.492(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
O33 C34 1.331(3) . ?
O33 B37 1.480(4) . ?
C34 N35 1.299(3) . ?
C34 C38 1.441(4) . ?
N35 N36 1.405(3) . ?
N36 B37 1.562(4) . ?
N36 C55 1.307(4) . ?
B37 F63 1.374(4) . ?
B37 F64 1.366(5) . ?
C38 S39 1.715(3) . ?
C38 C42 1.364(4) . ?
S39 C40 1.723(3) . ?
C40 C41 1.363(5) . ?
C40 C43 1.432(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.397(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.190(5) . ?
C44 C45 1.436(5) . ?
C45 C46 1.387(5) . ?
C45 C50 1.378(5) . ?
C46 H46 0.9300 . ?
C46 C47 1.374(5) . ?
C47 H47 0.9300 . ?
C47 C48 1.369(5) . ?
C48 C49 1.384(5) . ?
C48 C51 1.499(5) . ?
C49 H49 0.9300 . ?
C49 C50 1.371(5) . ?
C50 H50 0.9300 . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C51 H51C 0.9700 . ?
C51 H51D 0.9700 . ?
C51 C52A 1.489(8) . ?
C51 C52B 1.530(8) . ?
C55 H55 0.9300 . ?
C55 C56 1.393(4) . ?
C56 N57 1.394(4) . ?
C56 C60 1.398(4) . ?
N57 H57 0.86(3) . ?
N57 C58 1.351(4) . ?
C58 C59 1.381(5) . ?
C58 C61 1.489(5) . ?
C59 H59 0.9300 . ?
C59 C60 1.382(4) . ?
C60 C62 1.496(5) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?

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
C2 O1 B5 107.8(2) . . ?
C53Bb C52Bb C51 116.0(8) . . ?
O1 C2 C6 117.8(2) . . ?
C53Aa C52Aa C51 103.8(8) . . ?
C53Aa C52Aa H52A 111.0 . . ?
H52Aa C52Aa H52B 109.0 . . ?
N3 C2 O1 119.1(2) . . ?
N3 C2 C6 123.1(3) . . ?
C2 N3 N4 104.3(2) . . ?
N3 N4 B5 110.4(2) . . ?
C23 N4 N3 120.7(2) . . ?
C23 N4 B5 128.9(3) . . ?
O1 B5 N4 98.2(2) . . ?
F31 B5 O1 112.9(3) . . ?
C53Aa C52Aa H52B 111.0 . . ?
C54Aa C53Aa H53A 109.6 . . ?
C52Aa C53Aa H53A 109.6 . . ?
C54Aa C53Aa H53B 109.6 . . ?
C52Aa C53Aa H53B 109.6 . . ?
H53Aa C53Aa H53B 108.1 . . ?
F31 B5 N4 112.6(3) . . ?
F31 B5 F32 110.9(3) . . ?
F32 B5 O1 110.3(3) . . ?
F32 B5 N4 111.3(3) . . ?
C2 C6 S7 121.8(2) . . ?
C10 C6 C2 126.8(3) . . ?
C10 C6 S7 111.5(2) . . ?
C6 S7 C8 91.62(15) . . ?
C9 C8 S7 110.8(2) . . ?
C9 C8 C11 129.5(3) . . ?
C52Aa C53Aa C54A 110.4(15) . . ?
C53Aa C54Aa H54A 109.5 . . ?
C53Aa C54Aa H54B 109.5 . . ?
H54Aa C54Aa H54B 109.5 . . ?
H54Aa C54Aa H54C 109.5 . . ?
C53Aa C54Aa H54C 109.5 . . ?
H54Ba C54Aa H54C 109.5 . . ?
C54Bb C53Bb C52B 117.7(10) . . ?
C53Bb C52Bb H52C 108.3 . . ?
H52Cb C52Bb H52D 107.4 . . ?
C53Bb C52Bb H52D 108.3 . . ?
C52Bb C53Bb H53C 107.9 . . ?
C54Bb C53Bb H53C 107.9 . . ?
H53Cb C53Bb H53D 107.2 . . ?
C54Bb C53Bb H53D 107.9 . . ?
C52Bb C53Bb H53D 107.9 . . ?
C53Bb C54Bb H54D 109.5 . . ?
H54Db C54Bb H54E 109.5 . . ?
C53Bb C54Bb H54E 109.5 . . ?
H54Db C54Bb H54F 109.5 . . ?
C53Bb C54Bb H54F 109.5 . . ?
H54Eb C54Bb H54F 109.5 . . ?
C52Aa C51 C48 127.6(7) . . ?
C52Aa C51 H51A 105.4 . . ?
C52Aa C51 H51B 105.4 . . ?
H51Aa C51 H51B 106.0 . . ?
C52Bb C51 H51C 110.3 . . ?
H51Cb C51 H51D 108.6 . . ?
C11 C8 S7 119.7(3) . . ?
C8 C9 H9 123.3 . . ?
C8 C9 C10 113.4(3) . . ?
C10 C9 H9 123.3 . . ?
C6 C10 C9 112.8(3) . . ?
C6 C10 H10 123.6 . . ?
C9 C10 H10 123.6 . . ?
C12 C11 C8 178.8(4) . . ?
C11 C12 C13 178.5(4) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 C18 117.7(3) . . ?
C18 C13 C12 121.5(3) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(3) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 117.7(3) . . ?
C15 C16 C19 121.2(4) . . ?
C17 C16 C19 121.0(4) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.2(4) . . ?
C17 C18 H18 119.4 . . ?
C16 C19 H19A 109.1 . . ?
C16 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 C16 112.4(3) . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 C19 114.2(4) . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C20 C21 H21A 109.7 . . ?
C20 C21 H21B 109.7 . . ?
C20 C21 C22 109.8(5) . . ?
H21A C21 H21B 108.2 . . ?
C22 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 H23 115.4 . . ?
N4 C23 C24 129.1(3) . . ?
C52Bb C51 H51D 110.3 . . ?
C24 C23 H23 115.4 . . ?
C23 C24 C28 127.3(3) . . ?
N25 C24 C23 125.4(3) . . ?
N25 C24 C28 107.2(3) . . ?
C24 N25 H25 123.7(19) . . ?
C26 N25 C24 109.8(3) . . ?
C26 N25 H25 126(2) . . ?
N25 C26 C27 107.2(3) . . ?
N25 C26 C29 122.5(3) . . ?
C27 C26 C29 130.3(3) . . ?
C26 C27 H27 125.2 . . ?
C28 C27 C26 109.6(3) . . ?
C28 C27 H27 125.2 . . ?
C24 C28 C30 126.3(3) . . ?
C27 C28 C24 106.2(3) . . ?
C27 C28 C30 127.6(3) . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C34 O33 B37 107.9(2) . . ?
O33 C34 C38 117.7(3) . . ?
N35 C34 O33 119.3(3) . . ?
N35 C34 C38 122.9(3) . . ?
C34 N35 N36 104.0(2) . . ?
N35 N36 B37 110.4(2) . . ?
C55 N36 N35 120.9(2) . . ?
C55 N36 B37 128.7(3) . . ?
O33 B37 N36 98.1(3) . . ?
F63 B37 O33 110.4(3) . . ?
F63 B37 N36 111.2(3) . . ?
F64 B37 O33 112.8(3) . . ?
F64 B37 N36 112.5(3) . . ?
F64 B37 F63 111.2(3) . . ?
C34 C38 S39 121.8(2) . . ?
C42 C38 C34 126.6(3) . . ?
C42 C38 S39 111.6(2) . . ?
C38 S39 C40 91.43(16) . . ?
C41 C40 S39 111.0(3) . . ?
C41 C40 C43 128.9(3) . . ?
C43 C40 S39 120.0(3) . . ?
C40 C41 H41 123.4 . . ?
C40 C41 C42 113.3(3) . . ?
C42 C41 H41 123.4 . . ?
C38 C42 C41 112.7(3) . . ?
C38 C42 H42 123.7 . . ?
C41 C42 H42 123.7 . . ?
C44 C43 C40 178.3(4) . . ?
C43 C44 C45 179.1(4) . . ?
C46 C45 C44 121.4(3) . . ?
C50 C45 C44 120.7(3) . . ?
C50 C45 C46 117.9(3) . . ?
C45 C46 H46 119.7 . . ?
C47 C46 C45 120.7(4) . . ?
C47 C46 H46 119.7 . . ?
C46 C47 H47 119.0 . . ?
C48 C47 C46 122.0(4) . . ?
C48 C47 H47 119.0 . . ?
C47 C48 C49 116.8(3) . . ?
C47 C48 C51 120.8(4) . . ?
C49 C48 C51 122.4(4) . . ?
C48 C49 H49 118.9 . . ?
C50 C49 C48 122.2(3) . . ?
C50 C49 H49 118.9 . . ?
C45 C50 H50 119.8 . . ?
C49 C50 C45 120.5(3) . . ?
C49 C50 H50 119.8 . . ?
C48 C51 H51A 105.4 . . ?
C48 C51 H51B 105.4 . . ?
C48 C51 H51C 110.3 . . ?
C48 C51 H51D 110.3 . . ?
C48 C51 C52B 107.1(5) . . ?
N36 C55 H55 115.4 . . ?
N36 C55 C56 129.3(3) . . ?
C56 C55 H55 115.4 . . ?
C51 C52Aa H52A 111.0 . . ?
C51 C52Aa H52B 111.0 . . ?
C51 C52Bb H52C 108.3 . . ?
C55 C56 N57 125.3(3) . . ?
C55 C56 C60 127.6(3) . . ?
N57 C56 C60 107.1(3) . . ?
C56 N57 H57 123(2) . . ?
C58 N57 C56 109.3(3) . . ?
C58 N57 H57 128(2) . . ?
N57 C58 C59 107.6(3) . . ?
N57 C58 C61 121.7(3) . . ?
C59 C58 C61 130.7(3) . . ?
C58 C59 H59 125.4 . . ?
C58 C59 C60 109.3(3) . . ?
C60 C59 H59 125.4 . . ?
C56 C60 C62 125.9(3) . . ?
C59 C60 C56 106.7(3) . . ?
C59 C60 C62 127.4(3) . . ?
C58 C61 H61A 109.5 . . ?
C58 C61 H61B 109.5 . . ?
C58 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C60 C62 H62A 109.5 . . ?
C60 C62 H62B 109.5 . . ?
C60 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C51 C52Bb H52D 108.3 . . ?

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
O1 C2 N3 N4 -0.9(3) . . . . ?
O1 C2 C6 S7 171.8(2) . . . . ?
O1 C2 C6 C10 -7.0(4) . . . . ?
C2 O1 B5 N4 3.4(3) . . . . ?
C2 O1 B5 F31 122.3(3) . . . . ?
C2 O1 B5 F32 -112.9(3) . . . . ?
C2 N3 N4 B5 3.3(3) . . . . ?
C2 N3 N4 C23 -176.0(3) . . . . ?
C2 C6 S7 C8 -178.1(3) . . . . ?
C2 C6 C10 C9 178.3(3) . . . . ?
N3 C2 C6 S7 -6.9(4) . . . . ?
N3 C2 C6 C10 174.3(3) . . . . ?
N3 N4 B5 O1 -4.1(3) . . . . ?
N3 N4 B5 F31 -123.3(3) . . . . ?
N3 N4 B5 F32 111.5(3) . . . . ?
N3 N4 C23 C24 -4.1(5) . . . . ?
N4 C23 C24 N25 -5.1(5) . . . . ?
N4 C23 C24 C28 177.5(3) . . . . ?
B5 O1 C2 N3 -1.9(4) . . . . ?
B5 O1 C2 C6 179.3(3) . . . . ?
B5 N4 C23 C24 176.7(3) . . . . ?
C6 C2 N3 N4 177.7(2) . . . . ?
C6 S7 C8 C9 -1.0(3) . . . . ?
C6 S7 C8 C11 177.7(3) . . . . ?
S7 C6 C10 C9 -0.6(4) . . . . ?
S7 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C6 -0.1(4) . . . . ?
C10 C6 S7 C8 0.9(2) . . . . ?
C11 C8 C9 C10 -177.6(3) . . . . ?
C12 C13 C14 C15 178.5(3) . . . . ?
C12 C13 C18 C17 -178.8(5) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C13 C18 C17 1.9(7) . . . . ?
C14 C15 C16 C17 2.9(6) . . . . ?
C14 C15 C16 C19 -179.6(3) . . . . ?
C15 C16 C17 C18 -3.3(7) . . . . ?
C15 C16 C19 C20 -73.9(5) . . . . ?
C16 C17 C18 C13 0.9(8) . . . . ?
C16 C19 C20 C21 -177.4(4) . . . . ?
C17 C16 C19 C20 103.4(5) . . . . ?
C18 C13 C14 C15 -2.3(5) . . . . ?
C19 C16 C17 C18 179.2(5) . . . . ?
C19 C20 C21 C22 -175.8(5) . . . . ?
C23 N4 B5 O1 175.1(3) . . . . ?
C23 N4 B5 F31 56.0(4) . . . . ?
C23 N4 B5 F32 -69.3(4) . . . . ?
C23 C24 N25 C26 -177.2(3) . . . . ?
C23 C24 C28 C27 177.3(3) . . . . ?
C23 C24 C28 C30 -2.5(5) . . . . ?
C24 N25 C26 C27 -0.6(3) . . . . ?
C24 N25 C26 C29 179.4(3) . . . . ?
N25 C24 C28 C27 -0.5(3) . . . . ?
N25 C24 C28 C30 179.7(3) . . . . ?
N25 C26 C27 C28 0.3(4) . . . . ?
C26 C27 C28 C24 0.1(4) . . . . ?
C26 C27 C28 C30 180.0(3) . . . . ?
C28 C24 N25 C26 0.7(3) . . . . ?
C29 C26 C27 C28 -179.8(3) . . . . ?
O33 C34 N35 N36 0.7(3) . . . . ?
O33 C34 C38 S39 -171.4(2) . . . . ?
O33 C34 C38 C42 6.7(4) . . . . ?
C34 O33 B37 N36 -4.0(3) . . . . ?
C34 O33 B37 F63 112.3(3) . . . . ?
C34 O33 B37 F64 -122.7(3) . . . . ?
C34 N35 N36 B37 -3.5(3) . . . . ?
C34 N35 N36 C55 176.1(3) . . . . ?
C34 C38 S39 C40 177.8(2) . . . . ?
C34 C38 C42 C41 -178.1(3) . . . . ?
N35 C34 C38 S39 7.0(4) . . . . ?
N35 C34 C38 C42 -175.0(3) . . . . ?
N35 N36 B37 O33 4.6(3) . . . . ?
N35 N36 B37 F63 -111.1(3) . . . . ?
N35 N36 B37 F64 123.5(3) . . . . ?
N35 N36 C55 C56 3.7(4) . . . . ?
N36 C55 C56 N57 5.4(5) . . . . ?
N36 C55 C56 C60 -176.9(3) . . . . ?
B37 O33 C34 N35 2.5(4) . . . . ?
B37 O33 C34 C38 -179.1(3) . . . . ?
B37 N36 C55 C56 -176.8(3) . . . . ?
C38 C34 N35 N36 -177.6(2) . . . . ?
C38 S39 C40 C41 0.8(3) . . . . ?
C38 S39 C40 C43 -177.6(3) . . . . ?
S39 C38 C42 C41 0.1(4) . . . . ?
S39 C40 C41 C42 -0.9(4) . . . . ?
C40 C41 C42 C38 0.5(4) . . . . ?
C42 C38 S39 C40 -0.6(2) . . . . ?
C43 C40 C41 C42 177.4(3) . . . . ?
C44 C45 C46 C47 -179.5(4) . . . . ?
C44 C45 C50 C49 -180.0(3) . . . . ?
C45 C46 C47 C48 -0.6(8) . . . . ?
C46 C45 C50 C49 0.5(6) . . . . ?
C46 C47 C48 C49 0.7(7) . . . . ?
C46 C47 C48 C51 -177.9(5) . . . . ?
C47 C48 C49 C50 -0.2(6) . . . . ?
C47 C48 C51 C52Bb -113.6(8) . . . . ?
C47 C48 C51 C52Aa -143.2(7) . . . . ?
C49 C48 C51 C52Aa 38.3(9) . . . . ?
C49 C48 C51 C52Bb 68.0(8) . . . . ?
C48 C49 C50 C45 -0.4(6) . . . . ?
C48 C51 C52Bb C53Bb -179.5(10) . . . . ?
C48 C51 C52Aa C53Aa 74.0(12) . . . . ?
C50 C45 C46 C47 0.0(7) . . . . ?
C51 C52Bb C53Bb C54Bb 170.8(16) . . . . ?
C51 C52Aa C53Aa C54Aa -177.5(12) . . . . ?
C51 C48 C49 C50 178.3(4) . . . . ?
C55 N36 B37 O33 -174.9(3) . . . . ?
C55 N36 B37 F63 69.4(4) . . . . ?
C55 N36 B37 F64 -56.1(4) . . . . ?
C55 C56 N57 C58 177.3(3) . . . . ?
C55 C56 C60 C59 -177.5(3) . . . . ?
C55 C56 C60 C62 2.5(5) . . . . ?
C56 N57 C58 C59 0.8(3) . . . . ?
C56 N57 C58 C61 -178.9(3) . . . . ?
N57 C56 C60 C59 0.6(3) . . . . ?
N57 C56 C60 C62 -179.4(3) . . . . ?
N57 C58 C59 C60 -0.4(4) . . . . ?
C58 C59 C60 C56 -0.1(4) . . . . ?
C58 C59 C60 C62 179.9(3) . . . . ?
C60 C56 N57 C58 -0.8(3) . . . . ?
C61 C58 C59 C60 179.2(3) . . . . ?

_olex2_date_sample_data_collection 2022-03-18
_olex2_date_sample_submission    2022-03-09
_olex2_submission_original_sample_id JK285
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.616
####################################################################### 
# 
# 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_wdh1119
_database_code_depnum_ccdc_archive 'CCDC 2277475'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2022-09-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
luc.vanmeervelt@kuleuven.be
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 B F2 N3 O2'
_chemical_formula_sum            'C24 H24 B F2 N3 O2'
_chemical_formula_weight         435.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H24N3O1F2B1
_chemical_oxdiff_usercomment     'Jonathan - 2f'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5264(4)
_cell_length_b                   8.9825(5)
_cell_length_c                   17.3830(13)
_cell_angle_alpha                100.344(5)
_cell_angle_beta                 92.262(5)
_cell_angle_gamma                113.518(5)
_cell_volume                     1191.76(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2944
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.3360
_cell_measurement_theta_min      2.7790
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19076
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.531
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00   30.00    --  -17.15 -99.00   0.00   45
  2  ω    -47.00  53.00   1.00   30.00    --  -17.15  77.00-120.00  100
  3  ω    -20.00  25.00   1.00   30.00    --  -17.15 -99.00 -90.00   45
  4  ω    -87.00  13.00   1.00   30.00    --  -17.15 -77.00 120.00  100
  5  ω    -50.00  40.00   1.00   30.00    --   18.87 -57.00 -30.00   90
  6  ω    -50.00  40.00   1.00   30.00    --   18.87 -57.00   0.00   90
  7  ω    -75.00 -40.00   1.00   30.00    --  -17.15 125.00-158.00   35
  8  ω    -47.00  53.00   1.00   30.00    --  -17.15  77.00 120.00  100
  9  ω     -3.00  88.00   1.00   30.00    --   18.87  57.00  30.00   91
 10  ω      2.00  76.00   1.00   30.00    --   18.87-125.00 123.00   74
 11  ω     -3.00  88.00   1.00   30.00    --   18.87  57.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0371014000
_diffrn_orient_matrix_UB_12      -0.0387453000
_diffrn_orient_matrix_UB_13      -0.0395601000
_diffrn_orient_matrix_UB_21      -0.0814414000
_diffrn_orient_matrix_UB_22      -0.0390204000
_diffrn_orient_matrix_UB_23      0.0130365000
_diffrn_orient_matrix_UB_31      -0.0186702000
_diffrn_orient_matrix_UB_32      0.0688878000
_diffrn_orient_matrix_UB_33      -0.0034659000
_diffrn_oxdiff_ac4_digest_frames 
;
01be0fb071f1fec633ca10d5f629f9eddf00027bc47
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1983
_reflns_number_total             4863
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.1977
_refine_ls_R_factor_gt           0.0966
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1346P)²+0.3187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2568
_refine_ls_wR_factor_ref         0.3255
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19A-C20A = C20A-C21A = C21A-C22A = C19B-C20B = C20B-C21B = C21B-C22B
 1.534 with sigma of 0.01
 C13-C14A = C14A-C15A = C15A-C16A = C16A-C17A = C17A-C18A = C18A-C13
 1.394 with sigma of 0.01
 C13-C14B = C14B-C15B = C15B-C16B = C16B-C17B = C17B-C18B = C18B-C13
 1.394 with sigma of 0.01
 C16A-C19A = C16B-C19B
 1.522 with sigma of 0.01
 C19A-C21A = C20A-C22A = C19B-C21B = C20B-C22B
 2.564 with sigma of 0.01
3. Restrained planarity
 C13, C14A, C15A, C16A, C17A, C18A
 with sigma of 0.1
 C13, C14B, C15B, C16B, C17B, C18B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C22B) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.1
5. Rigid body (RIGU) restrains
 C13, C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.002
 C13, C14B, C15B, C16B, C17B, C18B, C19B, C20B, C21B, C22B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.002
6. Others
 Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(C17B)=Sof(H17B)=
 Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19C)=Sof(H19D)=Sof(C20B)=Sof(H20C)=
 Sof(H20D)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=1-FVAR(1)
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(C20A)=Sof(H20A)=
 Sof(H20B)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C22A)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C19A(H19A,H19B), C20A(H20A,H20B), C21A(H21A,H21B), C19B(H19C,H19D), C20B(H20C,
 H20D), C21B(H21C,H21D)
7.b Me refined with riding coordinates:
 C22B(H22D,H22E,H22F)
7.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C14A(H14A), C15A(H15A), C17A(H17A), C18A(H18A), C14B(H14B),
 C15B(H15B), C17B(H17B), C18B(H18B), C23(H23), N25(H25), C27(H27)
7.d Idealised Me refined as rotating group:
 C22A(H22A,H22B,H22C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9666(4) 0.3489(3) 0.13839(18) 0.0847(10) Uani 1 1 d . . . . .
C2 C 1.0582(6) 0.4950(5) 0.1222(3) 0.0683(11) Uani 1 1 d . . . . .
N3 N 1.1480(4) 0.5029(4) 0.0636(2) 0.0715(10) Uani 1 1 d . . . . .
N4 N 1.1209(4) 0.3389(4) 0.0329(2) 0.0726(10) Uani 1 1 d . . . . .
B5 B 0.9850(8) 0.2206(6) 0.0796(4) 0.0813(16) Uani 1 1 d . . . . .
C6 C 1.0561(6) 0.6419(5) 0.1711(3) 0.0751(12) Uani 1 1 d . . . . .
O7 O 0.9555(4) 0.6187(4) 0.23069(19) 0.0872(10) Uani 1 1 d . . . . .
C8 C 0.9674(7) 0.7726(6) 0.2661(3) 0.0932(15) Uani 1 1 d . . . . .
C9 C 1.0709(7) 0.8878(6) 0.2284(3) 0.1014(17) Uani 1 1 d . . . . .
H9 H 1.099387 1.001360 0.241017 0.122 Uiso 1 1 calc R U . . .
C10 C 1.1270(6) 0.8050(6) 0.1669(3) 0.0906(15) Uani 1 1 d . . . . .
H10 H 1.198200 0.851870 0.130584 0.109 Uiso 1 1 calc R U . . .
C11 C 0.8723(9) 0.7808(7) 0.3295(4) 0.1143(19) Uani 1 1 d . . . . .
C12 C 0.7931(10) 0.7900(8) 0.3838(4) 0.132(2) Uani 1 1 d . . . . .
C13 C 0.6904(11) 0.7951(9) 0.4461(5) 0.151(3) Uani 1 1 d D . . . .
C14A C 0.581(2) 0.6458(17) 0.4657(10) 0.181(8) Uani 0.497(11) 1 d D . P A 1
H14A H 0.563098 0.545080 0.432985 0.217 Uiso 0.497(11) 1 calc R U P A 1
C15A C 0.498(3) 0.646(2) 0.5331(10) 0.223(11) Uani 0.497(11) 1 d D . P A 1
H15A H 0.430101 0.545599 0.545761 0.267 Uiso 0.497(11) 1 calc R U P A 1
C16A C 0.517(3) 0.794(2) 0.5821(13) 0.203(11) Uani 0.497(11) 1 d D . P A 1
C17A C 0.642(2) 0.939(2) 0.5665(13) 0.151(8) Uani 0.497(11) 1 d D . P A 1
H17A H 0.661753 1.040867 0.599170 0.181 Uiso 0.497(11) 1 calc R U P A 1
C18A C 0.737(3) 0.9364(19) 0.5038(9) 0.138(6) Uani 0.497(11) 1 d D . P A 1
H18A H 0.833698 1.031189 0.500868 0.166 Uiso 0.497(11) 1 calc R U P A 1
C19A C 0.404(3) 0.797(6) 0.6483(17) 0.31(2) Uani 0.497(11) 1 d D . P A 1
H19A H 0.449605 0.909392 0.680274 0.368 Uiso 0.497(11) 1 calc R U P A 1
H19B H 0.413698 0.725061 0.681653 0.368 Uiso 0.497(11) 1 calc R U P A 1
C20A C 0.210(3) 0.744(4) 0.6213(13) 0.238(14) Uani 0.497(11) 1 d D . P A 1
H20A H 0.199577 0.816097 0.588026 0.285 Uiso 0.497(11) 1 calc R U P A 1
H20B H 0.163531 0.631602 0.589643 0.285 Uiso 0.497(11) 1 calc R U P A 1
C21A C 0.104(2) 0.749(2) 0.6883(9) 0.150(6) Uani 0.497(11) 1 d D . P A 1
H21A H 0.124328 0.863958 0.709016 0.180 Uiso 0.497(11) 1 calc R U P A 1
H21B H 0.143469 0.709374 0.730111 0.180 Uiso 0.497(11) 1 calc R U P A 1
C22A C -0.090(2) 0.647(3) 0.6667(11) 0.179(8) Uani 0.497(11) 1 d D . P A 1
H22A H -0.128838 0.675179 0.620937 0.269 Uiso 0.497(11) 1 calc R U P A 1
H22B H -0.149057 0.671482 0.709907 0.269 Uiso 0.497(11) 1 calc R U P A 1
H22C H -0.114518 0.531042 0.655698 0.269 Uiso 0.497(11) 1 calc R U P A 1
C14B C 0.5095(16) 0.7426(19) 0.4224(9) 0.174(7) Uani 0.503(11) 1 d D . P A 2
H14B H 0.469823 0.702276 0.368939 0.208 Uiso 0.503(11) 1 calc R U P A 2
C15B C 0.389(2) 0.748(2) 0.4739(11) 0.202(8) Uani 0.503(11) 1 d D . P A 2
H15B H 0.272934 0.707437 0.455046 0.242 Uiso 0.503(11) 1 calc R U P A 2
C16B C 0.445(3) 0.815(3) 0.5539(12) 0.211(10) Uani 0.503(11) 1 d D . P A 2
C17B C 0.620(3) 0.855(4) 0.5746(17) 0.212(11) Uani 0.503(11) 1 d D . P A 2
H17B H 0.655717 0.872516 0.627930 0.255 Uiso 0.503(11) 1 calc R U P A 2
C18B C 0.745(3) 0.872(3) 0.5236(8) 0.200(11) Uani 0.503(11) 1 d D . P A 2
H18B H 0.861461 0.932933 0.541728 0.241 Uiso 0.503(11) 1 calc R U P A 2
C19B C 0.341(4) 0.826(5) 0.6231(19) 0.295(16) Uani 0.503(11) 1 d D . P A 2
H19C H 0.404645 0.830011 0.671549 0.354 Uiso 0.503(11) 1 calc R U P A 2
H19D H 0.321281 0.926065 0.629010 0.354 Uiso 0.503(11) 1 calc R U P A 2
C20B C 0.169(4) 0.673(4) 0.6065(18) 0.236(14) Uani 0.503(11) 1 d D . P A 2
H20C H 0.137537 0.635780 0.549916 0.284 Uiso 0.503(11) 1 calc R U P A 2
H20D H 0.184245 0.584354 0.626020 0.284 Uiso 0.503(11) 1 calc R U P A 2
C21B C 0.020(4) 0.699(4) 0.6426(18) 0.300(18) Uani 0.503(11) 1 d D . P A 2
H21C H 0.002777 0.786093 0.622908 0.360 Uiso 0.503(11) 1 calc R U P A 2
H21D H 0.049981 0.735222 0.699261 0.360 Uiso 0.503(11) 1 calc R U P A 2
C22B C -0.150(4) 0.541(6) 0.624(3) 0.54(4) Uani 0.503(11) 1 d D U P A 2
H22D H -0.239327 0.564956 0.648769 0.808 Uiso 0.503(11) 1 calc R U P A 2
H22E H -0.182739 0.505259 0.568513 0.808 Uiso 0.503(11) 1 calc R U P A 2
H22F H -0.135508 0.454358 0.644910 0.808 Uiso 0.503(11) 1 calc R U P A 2
C23 C 1.2009(5) 0.3017(5) -0.0245(3) 0.0731(12) Uani 1 1 d . . . . .
H23 H 1.181336 0.190337 -0.038698 0.088 Uiso 1 1 calc R U . . .
C24 C 1.3122(5) 0.4066(5) -0.0676(3) 0.0715(12) Uani 1 1 d . . . . .
N25 N 1.3496(4) 0.5751(4) -0.0585(2) 0.0751(10) Uani 1 1 d . . . . .
H25 H 1.311261 0.630081 -0.024485 0.090 Uiso 1 1 calc R U . . .
C26 C 1.4542(6) 0.6380(6) -0.1107(3) 0.0820(13) Uani 1 1 d . . . . .
C27 C 1.4872(6) 0.5114(6) -0.1535(3) 0.0917(15) Uani 1 1 d . . . . .
H27 H 1.557132 0.521769 -0.193767 0.110 Uiso 1 1 calc R U . . .
C28 C 1.4015(6) 0.3678(5) -0.1279(3) 0.0779(12) Uani 1 1 d . . . . .
C29 C 1.5129(7) 0.8161(6) -0.1157(3) 0.1056(17) Uani 1 1 d . . . . .
H29A H 1.579625 0.885948 -0.066953 0.158 Uiso 1 1 calc R U . . .
H29B H 1.414354 0.839609 -0.125380 0.158 Uiso 1 1 calc R U . . .
H29C H 1.582358 0.837217 -0.157968 0.158 Uiso 1 1 calc R U . . .
C30 C 1.4026(7) 0.1995(6) -0.1569(3) 0.1081(17) Uani 1 1 d . . . . .
H30A H 1.410938 0.182892 -0.212397 0.162 Uiso 1 1 calc R U . . .
H30B H 1.297970 0.114652 -0.147082 0.162 Uiso 1 1 calc R U . . .
H30C H 1.499532 0.194037 -0.129529 0.162 Uiso 1 1 calc R U . . .
F31 F 1.0479(4) 0.1241(3) 0.11100(19) 0.1209(12) Uani 1 1 d . . . . .
F32 F 0.8324(4) 0.1232(3) 0.03166(18) 0.1157(11) Uani 1 1 d . . . . .


_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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.320(4) . ?
O1 B5 1.459(6) . ?
C14Aa H14A 0.9300 . ?
C14Aa C15A 1.390(9) . ?
C15Aa H15A 0.9300 . ?
C15Aa C16A 1.392(10) . ?
C16Aa C17A 1.396(10) . ?
C17Aa H17A 0.9300 . ?
C17Aa C18A 1.389(9) . ?
C18Aa H18A 0.9300 . ?
C16Aa C19A 1.532(10) . ?
C19Aa H19A 0.9700 . ?
C19Aa H19B 0.9700 . ?
C19Aa C20A 1.551(10) . ?
C20Aa H20A 0.9700 . ?
C20Aa H20B 0.9700 . ?
C20Aa C21A 1.510(10) . ?
C21Aa H21A 0.9700 . ?
C21Aa H21B 0.9700 . ?
C21Aa C22A 1.527(9) . ?
C22Aa H22A 0.9600 . ?
C22Aa H22B 0.9600 . ?
C22Aa H22C 0.9600 . ?
C14Bb H14B 0.9300 . ?
C14Bb C15B 1.398(9) . ?
C15Bb H15B 0.9300 . ?
C15Bb C16B 1.394(10) . ?
C16Bb C17B 1.395(10) . ?
C17Bb H17B 0.9300 . ?
C17Bb C18B 1.395(10) . ?
C18Bb H18B 0.9300 . ?
C16Bb C19B 1.535(10) . ?
C19Bb H19C 0.9700 . ?
C19Bb H19D 0.9700 . ?
C19Bb C20B 1.531(10) . ?
C20Bb H20C 0.9700 . ?
C20Bb H20D 0.9700 . ?
C20Bb C21B 1.517(10) . ?
C21Bb H21C 0.9700 . ?
C21Bb H21D 0.9700 . ?
C21Bb C22B 1.542(10) . ?
C22Bb H22D 0.9600 . ?
C22Bb H22E 0.9600 . ?
C22Bb H22F 0.9600 . ?
C2 N3 1.294(5) . ?
C2 C6 1.442(6) . ?
N3 N4 1.394(4) . ?
N4 B5 1.592(6) . ?
N4 C23 1.299(5) . ?
B5 F31 1.362(6) . ?
B5 F32 1.378(6) . ?
C6 O7 1.363(5) . ?
C6 C10 1.361(6) . ?
O7 C8 1.370(5) . ?
C8 C9 1.356(7) . ?
C8 C11 1.403(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.402(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.193(8) . ?
C12 C13 1.424(9) . ?
C13 C14A 1.406(9) . ?
C13 C18A 1.372(9) . ?
C13 C14B 1.439(9) . ?
C13 C18B 1.367(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.396(6) . ?
C24 N25 1.393(5) . ?
C24 C28 1.394(6) . ?
N25 H25 0.8600 . ?
N25 C26 1.336(5) . ?
C26 C27 1.377(7) . ?
C26 C29 1.494(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.370(6) . ?
C28 C30 1.508(6) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C2 O1 B5 108.4(4) . . ?
C15Aa C14Aa C13 121.2(14) . . ?
O1 C2 C6 118.8(4) . . ?
N3 C2 O1 119.4(4) . . ?
C15Bb C14Bb C13 124.7(15) . . ?
C15Aa C14Aa H14A 119.4 . . ?
C14Aa C15Aa H15A 119.4 . . ?
C16Aa C15Aa H15A 119.4 . . ?
C14Aa C15Aa C16A 121.2(16) . . ?
C18Aa C17Aa C16A 122(2) . . ?
C15Aa C16Aa C17A 116.1(17) . . ?
C16Aa C17Aa H17A 119.0 . . ?
C18Aa C17Aa H17A 119.0 . . ?
C17Aa C18Aa H18A 119.6 . . ?
C15Aa C16Aa C19A 122(2) . . ?
C21Aa C20Aa C19A 113.9(10) . . ?
C17Aa C16Aa C19A 122(2) . . ?
C20Aa C19Aa H19A 108.4 . . ?
N3 C2 C6 121.8(4) . . ?
C2 N3 N4 104.9(3) . . ?
C16Aa C19Aa H19A 108.4 . . ?
C20Aa C19Aa H19B 108.4 . . ?
H19Aa C19Aa H19B 107.4 . . ?
N3 N4 B5 108.8(3) . . ?
C23 N4 N3 121.5(3) . . ?
C23 N4 B5 129.7(3) . . ?
O1 B5 N4 98.2(3) . . ?
F31 B5 O1 113.7(5) . . ?
F31 B5 N4 111.9(4) . . ?
F31 B5 F32 110.4(4) . . ?
C16Aa C19Aa H19B 108.4 . . ?
C16Aa C19Aa C20A 115.6(19) . . ?
C19Aa C20Aa H20A 108.8 . . ?
C21Aa C20Aa H20A 108.8 . . ?
H20Aa C20Aa H20B 107.7 . . ?
C19Aa C20Aa H20B 108.8 . . ?
F32 B5 O1 111.4(4) . . ?
F32 B5 N4 110.7(4) . . ?
O7 C6 C2 116.8(4) . . ?
C10 C6 C2 132.5(5) . . ?
C10 C6 O7 110.5(4) . . ?
C6 O7 C8 106.4(4) . . ?
O7 C8 C11 117.1(5) . . ?
C9 C8 O7 109.4(5) . . ?
C9 C8 C11 133.4(5) . . ?
C8 C9 H9 126.2 . . ?
C8 C9 C10 107.7(4) . . ?
C10 C9 H9 126.2 . . ?
C6 C10 C9 106.0(5) . . ?
C6 C10 H10 127.0 . . ?
C9 C10 H10 127.0 . . ?
C12 C11 C8 179.1(7) . . ?
C11 C12 C13 177.0(8) . . ?
C12 C13 C14B 115.8(9) . . ?
N4 C23 H23 115.7 . . ?
N4 C23 C24 128.6(4) . . ?
C24 C23 H23 115.7 . . ?
N25 C24 C23 124.3(4) . . ?
N25 C24 C28 106.9(4) . . ?
C28 C24 C23 128.7(4) . . ?
C24 N25 H25 125.2 . . ?
C26 N25 C24 109.5(4) . . ?
C26 N25 H25 125.2 . . ?
N25 C26 C27 107.5(4) . . ?
N25 C26 C29 121.3(5) . . ?
C27 C26 C29 131.2(5) . . ?
C26 C27 H27 125.2 . . ?
C28 C27 C26 109.7(5) . . ?
C28 C27 H27 125.2 . . ?
C24 C28 C30 125.5(4) . . ?
C27 C28 C24 106.5(4) . . ?
C27 C28 C30 128.0(5) . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C21Aa C20Aa H20B 108.8 . . ?
C22Aa C21Aa H21A 108.5 . . ?
C20Aa C21Aa H21A 108.5 . . ?
C22Aa C21Aa H21B 108.5 . . ?
C20Aa C21Aa H21B 108.5 . . ?
H21Aa C21Aa H21B 107.5 . . ?
C20Aa C21Aa C22A 115.0(9) . . ?
C21Aa C22Aa H22A 109.5 . . ?
H22Aa C22Aa H22B 109.5 . . ?
C21Aa C22Aa H22B 109.5 . . ?
C21Aa C22Aa H22C 109.5 . . ?
H22Ba C22Aa H22C 109.5 . . ?
H22Aa C22Aa H22C 109.5 . . ?
C16Bb C15Bb C14B 119.1(17) . . ?
C15Bb C14Bb H14B 117.7 . . ?
C16Bb C15Bb H15B 120.4 . . ?
C14Bb C15Bb H15B 120.4 . . ?
C20Bb C19Bb C16B 109(2) . . ?
C15Bb C16Bb C17B 114(2) . . ?
C18Bb C17Bb H17B 116.6 . . ?
C16Bb C17Bb H17B 116.6 . . ?
C16Bb C17Bb C18B 127(3) . . ?
C17Bb C18Bb H18B 121.2 . . ?
C15Bb C16Bb C19B 130(2) . . ?
C17Bb C16Bb C19B 116(2) . . ?
C21Bb C20Bb C19B 115.4(11) . . ?
C16Bb C19Bb H19C 109.9 . . ?
C20Bb C19Bb H19C 109.9 . . ?
C20Bb C19Bb H19D 109.9 . . ?
H19Cb C19Bb H19D 108.3 . . ?
C16Bb C19Bb H19D 109.9 . . ?
C21Bb C20Bb H20C 108.4 . . ?
C19Bb C20Bb H20C 108.4 . . ?
C19Bb C20Bb H20D 108.4 . . ?
C21Bb C20Bb H20D 108.4 . . ?
H20Cb C20Bb H20D 107.5 . . ?
C22Bb C21Bb H21C 108.9 . . ?
C20Bb C21Bb H21C 108.9 . . ?
C22Bb C21Bb H21D 108.9 . . ?
H21Cb C21Bb H21D 107.7 . . ?
C20Bb C21Bb H21D 108.9 . . ?
C20Bb C21Bb C22B 113.4(11) . . ?
C21Bb C22Bb H22D 109.5 . . ?
C21Bb C22Bb H22E 109.5 . . ?
H22Db C22Bb H22E 109.5 . . ?
C21Bb C22Bb H22F 109.5 . . ?
H22Db C22Bb H22F 109.5 . . ?
H22Eb C22Bb H22F 109.5 . . ?
C18Aa C13 C12 120.6(11) . . ?
C14Aa C13 C12 119.4(9) . . ?
C18Bb C13 C12 127.9(14) . . ?
C18Aa C13 C14A 116.1(12) . . ?
C18Bb C13 C14B 115.0(15) . . ?
C13 C14Aa H14A 119.4 . . ?
C13 C18Aa C17A 120.7(19) . . ?
C13 C18Aa H18A 119.6 . . ?
C13 C14Bb H14B 117.7 . . ?
C13 C18Bb C17B 118(2) . . ?
C13 C18Bb H18B 121.2 . . ?

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
C14Aa C15Aa C16Aa C17Aa -10(3) . . . . ?
C14Bb C15Bb C16Bb C17Bb -6(3) . . . . ?
C17Bb C16Bb C19Bb C20Bb -136(3) . . . . ?
C14Aa C15Aa C16Aa C19Aa 169(2) . . . . ?
C15Bb C16Bb C17Bb C18Bb 16(5) . . . . ?
C15Aa C16Aa C17Aa C18Aa 3(4) . . . . ?
C19Bb C20Bb C21Bb C22Bb -180(4) . . . . ?
C19Aa C16Aa C17Aa C18Aa -177(2) . . . . ?
C14Bb C15Bb C16Bb C19Bb -176(3) . . . . ?
C15Aa C16Aa C19Aa C20Aa -67(4) . . . . ?
C19Bb C16Bb C17Bb C18Bb -173(3) . . . . ?
C17Aa C16Aa C19Aa C20Aa 112(3) . . . . ?
C16Bb C19Bb C20Bb C21Bb -151(3) . . . . ?
C16Aa C19Aa C20Aa C21Aa -180(3) . . . . ?
C19Aa C20Aa C21Aa C22Aa -161(2) . . . . ?
C15Bb C16Bb C19Bb C20Bb 34(5) . . . . ?
C16Bb C17Bb C18Bb C13 -22(4) . . . . ?
C16Aa C17Aa C18Aa C13 12(3) . . . . ?
O1 C2 N3 N4 -1.1(5) . . . . ?
O1 C2 C6 O7 -1.1(6) . . . . ?
O1 C2 C6 C10 -175.6(5) . . . . ?
C18Aa C13 C14Aa C15Aa 12.2(15) . . . . ?
C18Bb C13 C14Bb C15Bb -7.6(15) . . . . ?
C14Bb C13 C18Bb C17Bb 15(3) . . . . ?
C14Aa C13 C18Aa C17Aa -19(2) . . . . ?
C2 O1 B5 N4 4.1(5) . . . . ?
C2 O1 B5 F31 122.4(4) . . . . ?
C2 O1 B5 F32 -112.0(4) . . . . ?
C2 N3 N4 B5 3.8(4) . . . . ?
C2 N3 N4 C23 -175.9(4) . . . . ?
C2 C6 O7 C8 -177.2(4) . . . . ?
C2 C6 C10 C9 176.2(5) . . . . ?
N3 C2 C6 O7 179.4(4) . . . . ?
N3 C2 C6 C10 4.9(8) . . . . ?
N3 N4 B5 O1 -4.8(5) . . . . ?
N3 N4 B5 F31 -124.6(4) . . . . ?
N3 N4 B5 F32 111.8(4) . . . . ?
N3 N4 C23 C24 -4.5(7) . . . . ?
N4 C23 C24 N25 -4.0(7) . . . . ?
N4 C23 C24 C28 178.3(4) . . . . ?
B5 O1 C2 N3 -2.4(6) . . . . ?
B5 O1 C2 C6 178.1(4) . . . . ?
B5 N4 C23 C24 176.0(4) . . . . ?
C6 C2 N3 N4 178.4(4) . . . . ?
C6 O7 C8 C9 0.9(5) . . . . ?
C6 O7 C8 C11 179.3(5) . . . . ?
O7 C6 C10 C9 1.5(5) . . . . ?
O7 C8 C9 C10 0.0(6) . . . . ?
C8 C9 C10 C6 -0.9(6) . . . . ?
C10 C6 O7 C8 -1.5(5) . . . . ?
C11 C8 C9 C10 -178.1(6) . . . . ?
C12 C13 C18Aa C17Aa -177.0(15) . . . . ?
C12 C13 C18Bb C17Bb -177.9(17) . . . . ?
C12 C13 C14Aa C15Aa 170.2(11) . . . . ?
C12 C13 C14Bb C15Bb -176.0(10) . . . . ?
C13 C14Aa C15Aa C16Aa 2(2) . . . . ?
C13 C14Bb C15Bb C16Bb 2.8(19) . . . . ?
C23 N4 B5 O1 174.8(4) . . . . ?
C23 N4 B5 F31 55.0(7) . . . . ?
C23 N4 B5 F32 -68.6(6) . . . . ?
C23 C24 N25 C26 -177.3(4) . . . . ?
C23 C24 C28 C27 177.4(4) . . . . ?
C23 C24 C28 C30 -3.4(8) . . . . ?
C24 N25 C26 C27 -0.7(5) . . . . ?
C24 N25 C26 C29 178.7(4) . . . . ?
N25 C24 C28 C27 -0.6(5) . . . . ?
N25 C24 C28 C30 178.5(4) . . . . ?
N25 C26 C27 C28 0.3(6) . . . . ?
C26 C27 C28 C24 0.2(5) . . . . ?
C26 C27 C28 C30 -178.9(5) . . . . ?
C28 C24 N25 C26 0.9(5) . . . . ?
C29 C26 C27 C28 -179.0(5) . . . . ?

_olex2_date_sample_data_collection 2022-08-30
_olex2_date_sample_submission    2022-08-29
_olex2_submission_original_sample_id 2f
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.605
_oxdiff_exptl_absorpt_empirical_full_min 0.503
####################################################################### 
# 
# 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_wdh1102
_database_code_depnum_ccdc_archive 'CCDC 2277474'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
luc.vanmeervelt@kuleuven.be
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11 H10 B F2 N3 O2)'
_chemical_formula_sum            'C22 H20 B2 F4 N6 O4'
_chemical_formula_weight         530.06
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 O2 N3 B1 F2'
_chemical_oxdiff_usercomment     JK084
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.3453(6)
_cell_length_b                   12.6030(6)
_cell_length_c                   14.0398(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.496(5)
_cell_angle_gamma                90
_cell_volume                     2392.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6533
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.4420
_cell_measurement_theta_min      2.9290
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24766
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.388
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00 -35.00   1.00    5.00    --  -17.15-178.00 -60.00   58
  2  ω    -90.00  56.00   1.00    5.00    --  -17.15   0.00-180.00  146
  3  ω     35.00  95.00   1.00    5.00    --   18.87 178.00  30.00   60
  4  ω    -43.00  55.00   1.00    5.00    --  -17.15  38.00-120.00   98
  5  ω    -20.00  25.00   1.00    5.00    --  -17.15 -99.00 -30.00   45
  6  ω    -90.00 -56.00   1.00    5.00    --  -17.15 -38.00 150.00   34
  7  ω    -11.00  89.00   1.00    5.00    --   18.87  77.00 120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0367164000
_diffrn_orient_matrix_UB_12      -0.0289229000
_diffrn_orient_matrix_UB_13      0.0125983000
_diffrn_orient_matrix_UB_21      0.0039005000
_diffrn_orient_matrix_UB_22      0.0359370000
_diffrn_orient_matrix_UB_23      0.0400354000
_diffrn_orient_matrix_UB_31      -0.0373361000
_diffrn_orient_matrix_UB_32      0.0321762000
_diffrn_orient_matrix_UB_33      -0.0334032000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3179
_reflns_number_total             4885
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0084(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0666P)²+0.8104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), N14(H14), C15(H15), C16(H16), C17(H17), C27(H27),
 C28(H28), C29(H29), N33(H33), C34(H34), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42085(11) 0.45780(13) 0.67024(13) 0.0593(5) Uani 1 1 d . . . . .
C2 C 0.32370(15) 0.46560(18) 0.64646(16) 0.0461(5) Uani 1 1 d . . . . .
N3 N 0.28217(12) 0.55848(14) 0.63183(14) 0.0472(4) Uani 1 1 d . . . . .
N4 N 0.36155(12) 0.63004(15) 0.64680(13) 0.0470(5) Uani 1 1 d . . . . .
B5 B 0.46267(19) 0.5656(2) 0.6809(2) 0.0553(7) Uani 1 1 d . . . . .
C6 C 0.26836(15) 0.36865(18) 0.63955(16) 0.0470(5) Uani 1 1 d . . . . .
O7 O 0.32232(12) 0.27803(13) 0.66442(13) 0.0641(5) Uani 1 1 d . . . . .
C8 C 0.2557(2) 0.1989(2) 0.6544(2) 0.0669(7) Uani 1 1 d . . . . .
H8 H 0.272375 0.127796 0.667178 0.080 Uiso 1 1 calc R U . . .
C9 C 0.16372(19) 0.2357(2) 0.62397(19) 0.0632(7) Uani 1 1 d . . . . .
H9 H 0.105982 0.196467 0.611713 0.076 Uiso 1 1 calc R U . . .
C10 C 0.17151(17) 0.3470(2) 0.61401(18) 0.0575(6) Uani 1 1 d . . . . .
H10 H 0.119708 0.395471 0.593765 0.069 Uiso 1 1 calc R U . . .
C11 C 0.34551(15) 0.73177(18) 0.63793(15) 0.0457(5) Uani 1 1 d . . . . .
C12 C 0.43403(17) 0.8017(2) 0.65362(19) 0.0591(6) Uani 1 1 d . . . . .
H12A H 0.493041 0.762694 0.688636 0.089 Uiso 1 1 calc R U . . .
H12B H 0.429260 0.862412 0.692990 0.089 Uiso 1 1 calc R U . . .
H12C H 0.436453 0.824610 0.589290 0.089 Uiso 1 1 calc R U . . .
C13 C 0.25149(16) 0.78145(18) 0.61449(16) 0.0467(5) Uani 1 1 d . . . . .
N14 N 0.16282(13) 0.73082(15) 0.60100(14) 0.0522(5) Uani 1 1 d . . . . .
H14 H 0.155461 0.663271 0.603548 0.063 Uiso 1 1 calc R U . . .
C15 C 0.08942(18) 0.8025(2) 0.5833(2) 0.0640(7) Uani 1 1 d . . . . .
H15 H 0.023181 0.787454 0.572229 0.077 Uiso 1 1 calc R U . . .
C16 C 0.1292(2) 0.9016(2) 0.5843(2) 0.0743(8) Uani 1 1 d . . . . .
H16 H 0.094850 0.965569 0.573735 0.089 Uiso 1 1 calc R U . . .
C17 C 0.2299(2) 0.8891(2) 0.60392(19) 0.0621(7) Uani 1 1 d . . . . .
H17 H 0.275214 0.943382 0.609109 0.075 Uiso 1 1 calc R U . . .
F18 F 0.51719(11) 0.58639(13) 0.77979(12) 0.0795(5) Uani 1 1 d . . . . .
F19 F 0.51761(10) 0.58076(12) 0.61901(13) 0.0765(5) Uani 1 1 d . . . . .
O20 O 0.91543(11) 0.68373(13) 0.65484(13) 0.0607(5) Uani 1 1 d . . . . .
C21 C 0.81811(16) 0.67428(18) 0.62826(16) 0.0480(5) Uani 1 1 d . . . . .
N22 N 0.77927(13) 0.58060(14) 0.62228(14) 0.0481(5) Uani 1 1 d . . . . .
N23 N 0.86050(13) 0.51081(15) 0.64599(13) 0.0489(5) Uani 1 1 d . . . . .
B24 B 0.9596(2) 0.5773(2) 0.6733(2) 0.0616(8) Uani 1 1 d . . . . .
C25 C 0.75996(17) 0.76994(18) 0.60738(17) 0.0508(6) Uani 1 1 d . . . . .
O26 O 0.80863(17) 0.86418(16) 0.62196(17) 0.0904(6) Uani 1 1 d . . . . .
C27 C 0.7335(4) 0.9386(3) 0.5953(3) 0.1161(15) Uani 1 1 d . . . . .
H27 H 0.743392 1.011599 0.596108 0.139 Uiso 1 1 calc R U . . .
C28 C 0.6476(3) 0.8932(3) 0.5690(3) 0.1191(15) Uani 1 1 d . . . . .
H28 H 0.586838 0.927715 0.550649 0.143 Uiso 1 1 calc R U . . .
C29 C 0.66213(18) 0.7817(2) 0.5731(2) 0.0725(8) Uani 1 1 d . . . . .
H29 H 0.614182 0.728834 0.555665 0.087 Uiso 1 1 calc R U . . .
C30 C 0.84746(16) 0.40803(18) 0.64743(16) 0.0474(5) Uani 1 1 d . . . . .
C31 C 0.93818(18) 0.3409(2) 0.6699(2) 0.0652(7) Uani 1 1 d . . . . .
H31A H 0.995606 0.383432 0.702104 0.098 Uiso 1 1 calc R U . . .
H31B H 0.942293 0.312369 0.608017 0.098 Uiso 1 1 calc R U . . .
H31C H 0.934905 0.283852 0.713950 0.098 Uiso 1 1 calc R U . . .
C32 C 0.75551(16) 0.35651(18) 0.63053(16) 0.0462(5) Uani 1 1 d . . . . .
N33 N 0.66470(13) 0.40525(15) 0.61067(13) 0.0493(5) Uani 1 1 d . . . . .
H33 H 0.654436 0.472502 0.603956 0.059 Uiso 1 1 calc R U . . .
C34 C 0.59505(18) 0.3319(2) 0.60347(18) 0.0574(6) Uani 1 1 d . . . . .
H34 H 0.528194 0.345439 0.590358 0.069 Uiso 1 1 calc R U . . .
C35 C 0.63859(19) 0.2335(2) 0.61862(18) 0.0612(7) Uani 1 1 d . . . . .
H35 H 0.606911 0.168929 0.617802 0.073 Uiso 1 1 calc R U . . .
C36 C 0.73874(19) 0.24825(19) 0.63539(18) 0.0566(6) Uani 1 1 d . . . . .
H36 H 0.786265 0.195089 0.647711 0.068 Uiso 1 1 calc R U . . .
F37 F 1.01719(12) 0.56447(14) 0.77222(13) 0.0932(6) Uani 1 1 d . . . . .
F38 F 1.01208(11) 0.55704(13) 0.60938(14) 0.0849(5) Uani 1 1 d . . . . .


_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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.324(2) . ?
O1 B5 1.472(3) . ?
C2 N3 1.298(3) . ?
C2 C6 1.443(3) . ?
N3 N4 1.412(2) . ?
N4 B5 1.591(3) . ?
N4 C11 1.301(3) . ?
B5 F18 1.372(3) . ?
B5 F19 1.368(3) . ?
C6 O7 1.358(3) . ?
C6 C10 1.342(3) . ?
O7 C8 1.355(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.328(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.418(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.500(3) . ?
C11 C13 1.422(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N14 1.378(3) . ?
C13 C17 1.388(3) . ?
N14 H14 0.8600 . ?
N14 C15 1.346(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9300 . ?
O20 C21 1.325(3) . ?
O20 B24 1.469(3) . ?
C21 N22 1.296(3) . ?
C21 C25 1.439(3) . ?
N22 N23 1.408(2) . ?
N23 B24 1.583(3) . ?
N23 C30 1.310(3) . ?
B24 F37 1.368(3) . ?
B24 F38 1.374(3) . ?
C25 O26 1.358(3) . ?
C25 C29 1.331(3) . ?
O26 C27 1.383(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.297(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.419(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.495(3) . ?
C30 C32 1.417(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 N33 1.382(3) . ?
C32 C36 1.391(3) . ?
N33 H33 0.8600 . ?
N33 C34 1.340(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.373(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.389(3) . ?
C36 H36 0.9300 . ?

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
C2 O1 B5 108.43(17) . . ?
O1 C2 C6 117.61(19) . . ?
N3 C2 O1 119.7(2) . . ?
N3 C2 C6 122.67(19) . . ?
C2 N3 N4 104.33(17) . . ?
N3 N4 B5 109.12(17) . . ?
C11 N4 N3 120.46(17) . . ?
C11 N4 B5 130.28(19) . . ?
O1 B5 N4 98.10(17) . . ?
F18 B5 O1 110.8(2) . . ?
F18 B5 N4 111.2(2) . . ?
F19 B5 O1 111.5(2) . . ?
F19 B5 N4 113.4(2) . . ?
F19 B5 F18 111.2(2) . . ?
O7 C6 C2 116.19(19) . . ?
C10 C6 C2 133.4(2) . . ?
C10 C6 O7 110.4(2) . . ?
C8 O7 C6 105.67(18) . . ?
O7 C8 H8 124.2 . . ?
C9 C8 O7 111.6(2) . . ?
C9 C8 H8 124.2 . . ?
C8 C9 H9 127.0 . . ?
C8 C9 C10 105.9(2) . . ?
C10 C9 H9 127.0 . . ?
C6 C10 C9 106.5(2) . . ?
C6 C10 H10 126.8 . . ?
C9 C10 H10 126.8 . . ?
N4 C11 C12 116.8(2) . . ?
N4 C11 C13 125.4(2) . . ?
C13 C11 C12 117.8(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N14 C13 C11 126.0(2) . . ?
N14 C13 C17 106.0(2) . . ?
C17 C13 C11 128.0(2) . . ?
C13 N14 H14 125.0 . . ?
C15 N14 C13 110.1(2) . . ?
C15 N14 H14 125.0 . . ?
N14 C15 H15 125.9 . . ?
N14 C15 C16 108.2(2) . . ?
C16 C15 H15 125.9 . . ?
C15 C16 H16 126.3 . . ?
C15 C16 C17 107.5(2) . . ?
C17 C16 H16 126.3 . . ?
C13 C17 H17 125.9 . . ?
C16 C17 C13 108.3(2) . . ?
C16 C17 H17 125.9 . . ?
C21 O20 B24 108.65(18) . . ?
O20 C21 C25 117.8(2) . . ?
N22 C21 O20 119.3(2) . . ?
N22 C21 C25 122.8(2) . . ?
C21 N22 N23 104.46(17) . . ?
N22 N23 B24 109.39(18) . . ?
C30 N23 N22 120.67(18) . . ?
C30 N23 B24 129.9(2) . . ?
O20 B24 N23 98.08(18) . . ?
F37 B24 O20 111.5(2) . . ?
F37 B24 N23 111.9(2) . . ?
F37 B24 F38 111.4(2) . . ?
F38 B24 O20 110.6(2) . . ?
F38 B24 N23 112.8(2) . . ?
O26 C25 C21 117.9(2) . . ?
C29 C25 C21 129.5(2) . . ?
C29 C25 O26 112.6(2) . . ?
C25 O26 C27 103.8(3) . . ?
O26 C27 H27 124.5 . . ?
C28 C27 O26 111.0(3) . . ?
C28 C27 H27 124.5 . . ?
C27 C28 H28 125.9 . . ?
C27 C28 C29 108.2(3) . . ?
C29 C28 H28 125.9 . . ?
C25 C29 C28 104.4(3) . . ?
C25 C29 H29 127.8 . . ?
C28 C29 H29 127.8 . . ?
N23 C30 C31 116.4(2) . . ?
N23 C30 C32 125.5(2) . . ?
C32 C30 C31 118.2(2) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N33 C32 C30 126.3(2) . . ?
N33 C32 C36 106.21(19) . . ?
C36 C32 C30 127.4(2) . . ?
C32 N33 H33 125.1 . . ?
C34 N33 C32 109.7(2) . . ?
C34 N33 H33 125.1 . . ?
N33 C34 H34 125.6 . . ?
N33 C34 C35 108.8(2) . . ?
C35 C34 H34 125.6 . . ?
C34 C35 H35 126.4 . . ?
C34 C35 C36 107.2(2) . . ?
C36 C35 H35 126.4 . . ?
C32 C36 H36 126.0 . . ?
C35 C36 C32 108.0(2) . . ?
C35 C36 H36 126.0 . . ?

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
O1 C2 N3 N4 0.3(3) . . . . ?
O1 C2 C6 O7 3.9(3) . . . . ?
O1 C2 C6 C10 -176.9(2) . . . . ?
C2 O1 B5 N4 -4.9(2) . . . . ?
C2 O1 B5 F18 111.5(2) . . . . ?
C2 O1 B5 F19 -124.1(2) . . . . ?
C2 N3 N4 B5 -3.7(2) . . . . ?
C2 N3 N4 C11 -179.85(19) . . . . ?
C2 C6 O7 C8 178.8(2) . . . . ?
C2 C6 C10 C9 -178.8(2) . . . . ?
N3 C2 C6 O7 -175.0(2) . . . . ?
N3 C2 C6 C10 4.1(4) . . . . ?
N3 N4 B5 O1 5.3(2) . . . . ?
N3 N4 B5 F18 -110.8(2) . . . . ?
N3 N4 B5 F19 122.9(2) . . . . ?
N3 N4 C11 C12 -179.11(18) . . . . ?
N3 N4 C11 C13 0.7(3) . . . . ?
N4 C11 C13 N14 2.5(3) . . . . ?
N4 C11 C13 C17 -179.9(2) . . . . ?
B5 O1 C2 N3 3.4(3) . . . . ?
B5 O1 C2 C6 -175.6(2) . . . . ?
B5 N4 C11 C12 5.7(3) . . . . ?
B5 N4 C11 C13 -174.5(2) . . . . ?
C6 C2 N3 N4 179.29(19) . . . . ?
C6 O7 C8 C9 0.5(3) . . . . ?
O7 C6 C10 C9 0.4(3) . . . . ?
O7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C6 -0.1(3) . . . . ?
C10 C6 O7 C8 -0.5(3) . . . . ?
C11 N4 B5 O1 -179.1(2) . . . . ?
C11 N4 B5 F18 64.8(3) . . . . ?
C11 N4 B5 F19 -61.4(3) . . . . ?
C11 C13 N14 C15 177.8(2) . . . . ?
C11 C13 C17 C16 -178.0(2) . . . . ?
C12 C11 C13 N14 -177.6(2) . . . . ?
C12 C11 C13 C17 0.0(3) . . . . ?
C13 N14 C15 C16 0.4(3) . . . . ?
N14 C13 C17 C16 0.0(3) . . . . ?
N14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C13 0.3(3) . . . . ?
C17 C13 N14 C15 -0.2(3) . . . . ?
O20 C21 N22 N23 -1.5(3) . . . . ?
O20 C21 C25 O26 -3.8(3) . . . . ?
O20 C21 C25 C29 174.9(3) . . . . ?
C21 O20 B24 N23 1.8(2) . . . . ?
C21 O20 B24 F37 -115.6(2) . . . . ?
C21 O20 B24 F38 119.9(2) . . . . ?
C21 N22 N23 B24 2.6(2) . . . . ?
C21 N22 N23 C30 179.7(2) . . . . ?
C21 C25 O26 C27 179.7(2) . . . . ?
C21 C25 C29 C28 179.0(3) . . . . ?
N22 C21 C25 O26 176.0(2) . . . . ?
N22 C21 C25 C29 -5.3(4) . . . . ?
N22 N23 B24 O20 -2.7(2) . . . . ?
N22 N23 B24 F37 114.4(2) . . . . ?
N22 N23 B24 F38 -119.1(2) . . . . ?
N22 N23 C30 C31 177.89(19) . . . . ?
N22 N23 C30 C32 -2.7(3) . . . . ?
N23 C30 C32 N33 -0.6(4) . . . . ?
N23 C30 C32 C36 -177.1(2) . . . . ?
B24 O20 C21 N22 -0.4(3) . . . . ?
B24 O20 C21 C25 179.5(2) . . . . ?
B24 N23 C30 C31 -5.6(3) . . . . ?
B24 N23 C30 C32 173.7(2) . . . . ?
C25 C21 N22 N23 178.69(19) . . . . ?
C25 O26 C27 C28 1.2(4) . . . . ?
O26 C25 C29 C28 -2.2(3) . . . . ?
O26 C27 C28 C29 -2.5(5) . . . . ?
C27 C28 C29 C25 2.9(5) . . . . ?
C29 C25 O26 C27 0.8(3) . . . . ?
C30 N23 B24 O20 -179.5(2) . . . . ?
C30 N23 B24 F37 -62.4(3) . . . . ?
C30 N23 B24 F38 64.1(3) . . . . ?
C30 C32 N33 C34 -177.2(2) . . . . ?
C30 C32 C36 C35 177.0(2) . . . . ?
C31 C30 C32 N33 178.8(2) . . . . ?
C31 C30 C32 C36 2.2(3) . . . . ?
C32 N33 C34 C35 0.1(3) . . . . ?
N33 C32 C36 C35 -0.1(2) . . . . ?
N33 C34 C35 C36 -0.2(3) . . . . ?
C34 C35 C36 C32 0.2(3) . . . . ?
C36 C32 N33 C34 0.0(2) . . . . ?

_olex2_submission_original_sample_id JK084
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.492
_oxdiff_exptl_absorpt_empirical_full_min 0.631
####################################################################### 
# 
# 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_wdh1096
_database_code_depnum_ccdc_archive 'CCDC 2277473'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2019-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 B F2 N4 O'
_chemical_formula_sum            'C13 H13 B F2 N4 O'
_chemical_formula_weight         290.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 B1 F2 N4 O1'
_chemical_oxdiff_usercomment     'JK 23'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.0441(5)
_cell_length_b                   8.8128(5)
_cell_length_c                   12.0934(7)
_cell_angle_alpha                76.688(5)
_cell_angle_beta                 80.661(6)
_cell_angle_gamma                76.058(6)
_cell_volume                     704.50(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5915
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0850
_cell_measurement_theta_min      3.2490
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14570
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.430
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  40.00   1.00   10.00    --   18.87 -57.00 -60.00   90
  2  ω     -3.00  88.00   1.00   10.00    --   18.87  57.00-150.00   91
  3  ω    -20.00  61.00   1.00   10.00    --   18.87 -99.00 -90.00   81
  4  ω    -50.00  40.00   1.00   10.00    --   18.87 -57.00  60.00   90
  5  ω    -20.00  61.00   1.00   10.00    --   18.87 -99.00-180.00   81
  6  ω    -11.00  89.00   1.00   10.00    --   18.87  77.00  60.00  100
  7  ω    -20.00  25.00   1.00   10.00    --  -17.07 -99.00  90.00   45
  8  ω    -50.00  40.00   1.00   10.00    --   18.87 -57.00-180.00   90
  9  ω    -20.00  61.00   1.00   10.00    --   18.87 -99.00  30.00   81
 10  ω     -7.00  91.00   1.00   10.00    --   18.87  38.00-180.00   98
 11  ω     -3.00  88.00   1.00   10.00    --   18.87  57.00 -30.00   91
 12  ω    -86.00 -61.00   1.00   10.00    --  -17.07 -57.00 -90.00   25
 13  ω      1.00  76.00   1.00   10.00    --   18.87-124.00 124.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0348631000
_diffrn_orient_matrix_UB_12      -0.0021206000
_diffrn_orient_matrix_UB_13      -0.0581573000
_diffrn_orient_matrix_UB_21      0.0500164000
_diffrn_orient_matrix_UB_22      -0.0804365000
_diffrn_orient_matrix_UB_23      0.0161998000
_diffrn_orient_matrix_UB_31      -0.0847743000
_diffrn_orient_matrix_UB_32      -0.0262282000
_diffrn_orient_matrix_UB_33      -0.0059104000
_diffrn_oxdiff_ac4_digest_frames 
;
0127c2e1dadd5b194e7d90e300c2f3b61900027c9d8
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2154
_reflns_number_total             2876
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2876
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+0.2222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1403
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C17(H17), C12(H12), C21(H21), C20(H20), C18(H18)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F7 F 0.5981(2) 0.19769(17) 0.36902(11) 0.0856(5) Uani 1 1 d . . . . .
F6 F 0.3062(3) 0.12692(16) 0.40039(12) 0.0915(5) Uani 1 1 d . . . . .
O1 O 0.3186(2) 0.39562(16) 0.31688(11) 0.0609(4) Uani 1 1 d . . . . .
N3 N 0.3518(2) 0.31400(17) 0.50848(13) 0.0461(4) Uani 1 1 d . . . . .
N4 N 0.2703(2) 0.47825(17) 0.48501(13) 0.0457(4) Uani 1 1 d . . . . .
N10 N 0.2690(3) 0.4491(2) 0.72484(15) 0.0532(4) Uani 1 1 d . . . . .
C9 C 0.3374(3) 0.2919(2) 0.71404(15) 0.0447(4) Uani 1 1 d . . . . .
C8 C 0.3764(3) 0.2356(2) 0.61206(16) 0.0448(4) Uani 1 1 d . . . . .
H8 H 0.427124 0.126522 0.619232 0.054 Uiso 1 1 calc R . . . .
N19 N 0.0354(3) 0.9751(2) 0.1865(2) 0.0750(6) Uani 1 1 d . . . . .
C5 C 0.2570(3) 0.5117(2) 0.37608(16) 0.0458(4) Uani 1 1 d . . . . .
C16 C 0.1788(3) 0.6718(2) 0.31287(17) 0.0485(5) Uani 1 1 d . . . . .
C13 C 0.3616(3) 0.2002(2) 0.82415(16) 0.0488(5) Uani 1 1 d . . . . .
C17 C 0.1715(3) 0.6968(3) 0.19622(18) 0.0572(5) Uani 1 1 d . . . . .
H17 H 0.214708 0.612476 0.157787 0.069 Uiso 1 1 calc R . . . .
C15 C 0.4312(3) 0.0233(2) 0.85294(18) 0.0591(5) Uani 1 1 d . . . . .
H15A H 0.382194 -0.024919 0.802959 0.089 Uiso 1 1 calc GR . . . .
H15B H 0.383595 -0.015913 0.930778 0.089 Uiso 1 1 calc GR . . . .
H15C H 0.572485 -0.002999 0.843584 0.089 Uiso 1 1 calc GR . . . .
C12 C 0.3071(3) 0.3066(3) 0.89798(18) 0.0618(6) Uani 1 1 d . . . . .
H12 H 0.307989 0.279427 0.976930 0.074 Uiso 1 1 calc R . . . .
C11 C 0.2512(4) 0.4591(3) 0.83572(18) 0.0633(6) Uani 1 1 d . . . . .
C21 C 0.1118(3) 0.8018(2) 0.3663(2) 0.0605(5) Uani 1 1 d . . . . .
H21 H 0.113490 0.790419 0.444520 0.073 Uiso 1 1 calc R . . . .
C20 C 0.0423(3) 0.9490(3) 0.2989(3) 0.0730(7) Uani 1 1 d . . . . .
H20 H -0.002701 1.035752 0.334822 0.088 Uiso 1 1 calc R . . . .
C18 C 0.0992(3) 0.8487(3) 0.1379(2) 0.0675(6) Uani 1 1 d . . . . .
H18 H 0.094924 0.863559 0.059592 0.081 Uiso 1 1 calc R . . . .
B2 B 0.3991(4) 0.2471(3) 0.3953(2) 0.0581(6) Uani 1 1 d . . . . .
C14 C 0.1815(6) 0.6153(3) 0.8733(2) 0.1060(11) Uani 1 1 d . . . . .
H14A H 0.280540 0.677725 0.847994 0.159 Uiso 1 1 calc GR . . . .
H14B H 0.156733 0.596803 0.955225 0.159 Uiso 1 1 calc GR . . . .
H14C H 0.062311 0.671724 0.840860 0.159 Uiso 1 1 calc GR . . . .
H10 H 0.246(3) 0.524(3) 0.670(2) 0.067(7) Uiso 1 1 d . . . . .


_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_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F7 B2 1.371(3) . ?
F6 B2 1.359(3) . ?
O1 C5 1.330(2) . ?
O1 B2 1.476(3) . ?
N3 N4 1.403(2) . ?
N3 C8 1.300(2) . ?
N3 B2 1.568(3) . ?
N4 C5 1.296(2) . ?
N10 C9 1.382(2) . ?
N10 C11 1.348(3) . ?
N10 H10 0.82(2) . ?
C9 C8 1.396(3) . ?
C9 C13 1.403(3) . ?
C8 H8 0.9300 . ?
N19 C20 1.333(3) . ?
N19 C18 1.327(3) . ?
C5 C16 1.464(3) . ?
C16 C17 1.384(3) . ?
C16 C21 1.390(3) . ?
C13 C15 1.493(3) . ?
C13 C12 1.388(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C11 1.380(3) . ?
C11 C14 1.494(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.386(3) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C5 O1 B2 108.47(15) . . ?
N4 N3 B2 110.30(15) . . ?
C8 N3 N4 121.80(15) . . ?
C8 N3 B2 127.88(16) . . ?
C5 N4 N3 104.32(14) . . ?
C9 N10 H10 123.5(17) . . ?
C11 N10 C9 109.72(18) . . ?
C11 N10 H10 126.8(17) . . ?
N10 C9 C8 126.16(17) . . ?
N10 C9 C13 107.35(16) . . ?
C8 C9 C13 126.49(18) . . ?
N3 C8 C9 129.14(18) . . ?
N3 C8 H8 115.4 . . ?
C9 C8 H8 115.4 . . ?
C18 N19 C20 116.2(2) . . ?
O1 C5 C16 117.33(17) . . ?
N4 C5 O1 118.96(17) . . ?
N4 C5 C16 123.71(16) . . ?
C17 C16 C5 119.74(18) . . ?
C17 C16 C21 118.24(19) . . ?
C21 C16 C5 122.01(19) . . ?
C9 C13 C15 125.68(17) . . ?
C12 C13 C9 106.14(18) . . ?
C12 C13 C15 128.18(19) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 118.9(2) . . ?
C18 C17 H17 120.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C12 H12 125.4 . . ?
C11 C12 C13 109.21(19) . . ?
C11 C12 H12 125.4 . . ?
N10 C11 C12 107.58(18) . . ?
N10 C11 C14 121.7(2) . . ?
C12 C11 C14 130.7(2) . . ?
C16 C21 H21 121.1 . . ?
C20 C21 C16 117.7(2) . . ?
C20 C21 H21 121.1 . . ?
N19 C20 C21 124.7(2) . . ?
N19 C20 H20 117.6 . . ?
C21 C20 H20 117.6 . . ?
N19 C18 C17 124.1(2) . . ?
N19 C18 H18 117.9 . . ?
C17 C18 H18 117.9 . . ?
F7 B2 O1 111.74(19) . . ?
F7 B2 N3 111.19(19) . . ?
F6 B2 F7 110.26(19) . . ?
F6 B2 O1 113.2(2) . . ?
F6 B2 N3 112.16(19) . . ?
O1 B2 N3 97.81(15) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O1 C5 C16 C17 0.0(3) . . . . ?
O1 C5 C16 C21 -179.57(17) . . . . ?
N3 N4 C5 O1 -0.6(2) . . . . ?
N3 N4 C5 C16 179.99(16) . . . . ?
N4 N3 C8 C9 -2.2(3) . . . . ?
N4 N3 B2 F7 113.35(18) . . . . ?
N4 N3 B2 F6 -122.67(19) . . . . ?
N4 N3 B2 O1 -3.7(2) . . . . ?
N4 C5 C16 C17 179.49(17) . . . . ?
N4 C5 C16 C21 -0.1(3) . . . . ?
N10 C9 C8 N3 -2.6(3) . . . . ?
N10 C9 C13 C15 179.39(18) . . . . ?
N10 C9 C13 C12 -0.2(2) . . . . ?
C9 N10 C11 C12 -0.5(3) . . . . ?
C9 N10 C11 C14 179.5(2) . . . . ?
C9 C13 C12 C11 -0.1(2) . . . . ?
C8 N3 N4 C5 -175.95(16) . . . . ?
C8 N3 B2 F7 -68.0(3) . . . . ?
C8 N3 B2 F6 56.0(3) . . . . ?
C8 N3 B2 O1 174.96(17) . . . . ?
C8 C9 C13 C15 -1.1(3) . . . . ?
C8 C9 C13 C12 179.35(18) . . . . ?
C5 O1 B2 F7 -113.38(19) . . . . ?
C5 O1 B2 F6 121.43(19) . . . . ?
C5 O1 B2 N3 3.2(2) . . . . ?
C5 C16 C17 C18 -179.37(18) . . . . ?
C5 C16 C21 C20 179.34(18) . . . . ?
C16 C17 C18 N19 0.2(3) . . . . ?
C16 C21 C20 N19 -0.1(3) . . . . ?
C13 C9 C8 N3 177.92(18) . . . . ?
C13 C12 C11 N10 0.3(3) . . . . ?
C13 C12 C11 C14 -179.7(3) . . . . ?
C17 C16 C21 C20 -0.3(3) . . . . ?
C15 C13 C12 C11 -179.7(2) . . . . ?
C11 N10 C9 C8 -179.14(19) . . . . ?
C11 N10 C9 C13 0.4(2) . . . . ?
C21 C16 C17 C18 0.2(3) . . . . ?
C20 N19 C18 C17 -0.6(3) . . . . ?
C18 N19 C20 C21 0.5(3) . . . . ?
B2 O1 C5 N4 -2.0(2) . . . . ?
B2 O1 C5 C16 177.47(17) . . . . ?
B2 N3 N4 C5 2.8(2) . . . . ?
B2 N3 C8 C9 179.34(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.673
