# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_wdh1094
_database_code_depnum_ccdc_archive 'CCDC 1982532'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-11-12
_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         'C12 H12 B2 F4 N4 O'
_chemical_formula_sum            'C12 H12 B2 F4 N4 O'
_chemical_formula_weight         325.88
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N4 O1 B2 F4'
_chemical_oxdiff_usercomment     WDH-SD-38
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.2475(6)
_cell_length_b                   4.8212(2)
_cell_length_c                   15.1310(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.221(6)
_cell_angle_gamma                90
_cell_volume                     705.88(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4111
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8540
_cell_measurement_theta_min      2.8950
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73679
_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            'greenish yellow'
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8064
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.851
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  95.00   1.00   10.00    --   18.87 178.00  30.00   60
  2  ω     -7.00  91.00   1.00   10.00    --   18.87  38.00-180.00   98
  3  ω    -54.00  44.00   1.00   10.00    --   18.87 -38.00   0.00   98
  4  ω    -61.00  56.00   1.00   10.00    --  -17.07  19.00-150.00  117
  5  ω    -20.00  25.00   1.00   10.00    --  -17.07 -99.00   0.00   45
  6  ω    -50.00  40.00   1.00   10.00    --   18.87 -57.00-150.00   90
  7  ω     -3.00  68.00   1.00   10.00    --   18.87  57.00 -60.00   71
;
_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      -0.0671986000
_diffrn_orient_matrix_UB_12      0.0558634000
_diffrn_orient_matrix_UB_13      -0.0208784000
_diffrn_orient_matrix_UB_21      0.0020121000
_diffrn_orient_matrix_UB_22      -0.0372572000
_diffrn_orient_matrix_UB_23      -0.0448803000
_diffrn_orient_matrix_UB_31      -0.0293316000
_diffrn_orient_matrix_UB_32      -0.1307724000
_diffrn_orient_matrix_UB_33      0.0038893000
_diffrn_oxdiff_ac4_digest_frames 
;
01c6228ec08f6248d8e5f853fb35e765da000273461
;
_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         0.772
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2551
_reflns_number_total             2850
_reflns_odcompleteness_completeness 99.81
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.111
_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)+(0.0291P)²+0.1824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0857
_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:
 C7(H7), C10(H10), N16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_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
B1 B -0.6752(3) -0.2955(7) -0.8036(2) 0.0346(7) Uani 1 1 d . . . . .
N2 N -0.5501(2) -0.4687(5) -0.73687(14) 0.0320(5) Uani 1 1 d . . . . .
C3 C -0.4315(3) -0.5351(6) -0.74821(19) 0.0357(7) Uani 1 1 d . . . . .
O4 O -0.3502(2) -0.6960(5) -0.68364(14) 0.0485(6) Uani 1 1 d . . . . .
B5 B -0.4105(4) -0.7501(8) -0.6079(2) 0.0437(9) Uani 1 1 d . . . . .
N6 N -0.5521(3) -0.6006(5) -0.65466(15) 0.0370(6) Uani 1 1 d . . . . .
C7 C -0.6633(3) -0.5910(7) -0.63021(19) 0.0414(7) Uani 1 1 d . . . . .
H7 H -0.662893 -0.688105 -0.577025 0.050 Uiso 1 1 calc R . . . .
C8 C -0.7809(3) -0.4452(7) -0.67869(19) 0.0404(7) Uani 1 1 d . . . . .
C9 C -0.9056(3) -0.4074(9) -0.6599(2) 0.0503(9) Uani 1 1 d . . . . .
C10 C -0.9839(3) -0.2294(9) -0.7282(2) 0.0558(10) Uani 1 1 d . . . . .
H10 H -1.071982 -0.166216 -0.733621 0.067 Uiso 1 1 calc R . . . .
C11 C -0.9106(3) -0.1595(8) -0.7875(2) 0.0474(8) Uani 1 1 d . . . . .
N12 N -0.7864(2) -0.2900(6) -0.75758(15) 0.0380(6) Uani 1 1 d . . . . .
F13 F -0.62852(18) -0.0326(4) -0.81436(12) 0.0442(4) Uani 1 1 d . . . . .
F14 F -0.72052(17) -0.4235(4) -0.89036(10) 0.0427(4) Uani 1 1 d . . . . .
C15 C -0.3841(3) -0.4614(7) -0.82425(19) 0.0365(7) Uani 1 1 d . . . . .
N16 N -0.4367(3) -0.2576(6) -0.88947(17) 0.0429(6) Uani 1 1 d . . . . .
H16 H -0.503083 -0.146846 -0.890744 0.051 Uiso 1 1 calc R . . . .
C17 C -0.3670(3) -0.2591(8) -0.9516(2) 0.0487(8) Uani 1 1 d . . . . .
H17 H -0.382748 -0.140157 -1.002436 0.058 Uiso 1 1 calc R . . . .
C18 C -0.2705(3) -0.4624(8) -0.9274(2) 0.0527(9) Uani 1 1 d . . . . .
H18 H -0.208884 -0.507992 -0.958525 0.063 Uiso 1 1 calc R . . . .
C19 C -0.2803(3) -0.5908(8) -0.8474(2) 0.0508(9) Uani 1 1 d . . . . .
H19 H -0.226367 -0.737603 -0.815394 0.061 Uiso 1 1 calc R . . . .
F20 F -0.3349(2) -0.6237(5) -0.52636(12) 0.0605(6) Uani 1 1 d . . . . .
F21 F -0.4257(2) -1.0252(4) -0.59545(13) 0.0590(6) Uani 1 1 d . . . . .
C22 C -0.9427(4) -0.5383(11) -0.5813(3) 0.0719(13) Uani 1 1 d . . . . .
H22A H -0.886701 -0.459786 -0.522858 0.108 Uiso 1 1 calc GR . . . .
H22B H -0.926756 -0.734601 -0.580888 0.108 Uiso 1 1 calc GR . . . .
H22C H -1.038459 -0.504303 -0.590080 0.108 Uiso 1 1 calc GR . . . .
C23 C -0.9525(4) 0.0220(9) -0.8718(3) 0.0625(10) Uani 1 1 d . . . . .
H23A H -0.955564 -0.085324 -0.925878 0.094 Uiso 1 1 calc GR . . . .
H23B H -0.886654 0.169522 -0.863624 0.094 Uiso 1 1 calc GR . . . .
H23C H -1.042223 0.098718 -0.880206 0.094 Uiso 1 1 calc GR . . . .


_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
B1 N2 1.584(4) . ?
B1 N12 1.519(4) . ?
B1 F13 1.383(4) . ?
B1 F14 1.385(4) . ?
N2 C3 1.321(4) . ?
N2 N6 1.403(3) . ?
C3 O4 1.310(3) . ?
C3 C15 1.433(4) . ?
O4 B5 1.493(4) . ?
B5 N6 1.565(5) . ?
B5 F20 1.366(4) . ?
B5 F21 1.356(4) . ?
N6 C7 1.309(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(4) . ?
C8 C9 1.409(4) . ?
C8 N12 1.394(4) . ?
C9 C10 1.379(5) . ?
C9 C22 1.501(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(4) . ?
C11 N12 1.357(4) . ?
C11 C23 1.489(5) . ?
C15 N16 1.371(4) . ?
C15 C19 1.374(4) . ?
N16 H16 0.8600 . ?
N16 C17 1.355(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.354(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.392(5) . ?
C19 H19 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
N12 B1 N2 106.8(2) . . ?
F13 B1 N2 108.6(2) . . ?
F13 B1 N12 112.2(3) . . ?
F13 B1 F14 108.5(2) . . ?
F14 B1 N2 108.5(2) . . ?
F14 B1 N12 112.0(3) . . ?
C3 N2 B1 129.1(2) . . ?
C3 N2 N6 106.7(2) . . ?
N6 N2 B1 124.0(2) . . ?
N2 C3 C15 127.8(3) . . ?
O4 C3 N2 115.7(2) . . ?
O4 C3 C15 116.4(3) . . ?
C3 O4 B5 110.7(2) . . ?
O4 B5 N6 97.4(2) . . ?
F20 B5 O4 111.1(3) . . ?
F20 B5 N6 111.6(3) . . ?
F21 B5 O4 111.9(3) . . ?
F21 B5 N6 112.4(3) . . ?
F21 B5 F20 111.6(3) . . ?
N2 N6 B5 109.1(2) . . ?
C7 N6 N2 120.2(2) . . ?
C7 N6 B5 130.7(3) . . ?
N6 C7 H7 118.1 . . ?
N6 C7 C8 123.9(3) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 130.6(3) . . ?
C7 C8 N12 120.7(3) . . ?
N12 C8 C9 108.7(3) . . ?
C8 C9 C22 126.1(4) . . ?
C10 C9 C8 105.8(3) . . ?
C10 C9 C22 128.2(3) . . ?
C9 C10 H10 125.4 . . ?
C9 C10 C11 109.3(3) . . ?
C11 C10 H10 125.4 . . ?
C10 C11 C23 129.2(3) . . ?
N12 C11 C10 108.7(3) . . ?
N12 C11 C23 122.1(3) . . ?
C8 N12 B1 124.0(3) . . ?
C11 N12 B1 128.2(3) . . ?
C11 N12 C8 107.6(2) . . ?
N16 C15 C3 126.8(3) . . ?
N16 C15 C19 107.2(3) . . ?
C19 C15 C3 126.0(3) . . ?
C15 N16 H16 125.6 . . ?
C17 N16 C15 108.9(3) . . ?
C17 N16 H16 125.6 . . ?
N16 C17 H17 125.6 . . ?
C18 C17 N16 108.7(3) . . ?
C18 C17 H17 125.6 . . ?
C17 C18 H18 126.2 . . ?
C17 C18 C19 107.6(3) . . ?
C19 C18 H18 126.2 . . ?
C15 C19 C18 107.7(3) . . ?
C15 C19 H19 126.2 . . ?
C18 C19 H19 126.2 . . ?
C9 C22 H22A 109.5 . . ?
C9 C22 H22B 109.5 . . ?
C9 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
B1 N2 C3 O4 -175.9(3) . . . . ?
B1 N2 C3 C15 1.4(5) . . . . ?
B1 N2 N6 B5 180.0(3) . . . . ?
B1 N2 N6 C7 1.8(4) . . . . ?
N2 B1 N12 C8 -8.2(4) . . . . ?
N2 B1 N12 C11 177.9(3) . . . . ?
N2 C3 O4 B5 -3.8(4) . . . . ?
N2 C3 C15 N16 16.1(5) . . . . ?
N2 C3 C15 C19 -161.1(3) . . . . ?
N2 N6 C7 C8 -3.1(4) . . . . ?
C3 N2 N6 B5 4.1(3) . . . . ?
C3 N2 N6 C7 -174.1(3) . . . . ?
C3 O4 B5 N6 5.5(3) . . . . ?
C3 O4 B5 F20 -111.1(3) . . . . ?
C3 O4 B5 F21 123.4(3) . . . . ?
C3 C15 N16 C17 -177.9(3) . . . . ?
C3 C15 C19 C18 177.8(3) . . . . ?
O4 C3 C15 N16 -166.7(3) . . . . ?
O4 C3 C15 C19 16.1(4) . . . . ?
O4 B5 N6 N2 -5.7(3) . . . . ?
O4 B5 N6 C7 172.3(3) . . . . ?
B5 N6 C7 C8 179.1(3) . . . . ?
N6 N2 C3 O4 -0.4(3) . . . . ?
N6 N2 C3 C15 176.9(3) . . . . ?
N6 C7 C8 C9 -177.6(3) . . . . ?
N6 C7 C8 N12 -1.6(5) . . . . ?
C7 C8 C9 C10 176.4(3) . . . . ?
C7 C8 C9 C22 -3.9(6) . . . . ?
C7 C8 N12 B1 8.0(5) . . . . ?
C7 C8 N12 C11 -177.0(3) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C8 N12 B1 -175.2(3) . . . . ?
C9 C8 N12 C11 -0.1(4) . . . . ?
C9 C10 C11 N12 -0.2(4) . . . . ?
C9 C10 C11 C23 179.0(4) . . . . ?
C10 C11 N12 B1 175.0(3) . . . . ?
C10 C11 N12 C8 0.2(4) . . . . ?
N12 B1 N2 C3 178.3(3) . . . . ?
N12 B1 N2 N6 3.5(4) . . . . ?
N12 C8 C9 C10 0.0(4) . . . . ?
N12 C8 C9 C22 179.7(3) . . . . ?
F13 B1 N2 C3 -60.4(4) . . . . ?
F13 B1 N2 N6 124.7(2) . . . . ?
F13 B1 N12 C8 -127.1(3) . . . . ?
F13 B1 N12 C11 59.0(4) . . . . ?
F14 B1 N2 C3 57.4(4) . . . . ?
F14 B1 N2 N6 -117.4(3) . . . . ?
F14 B1 N12 C8 110.5(3) . . . . ?
F14 B1 N12 C11 -63.5(4) . . . . ?
C15 C3 O4 B5 178.6(3) . . . . ?
C15 N16 C17 C18 0.3(4) . . . . ?
N16 C15 C19 C18 0.1(4) . . . . ?
N16 C17 C18 C19 -0.2(4) . . . . ?
C17 C18 C19 C15 0.1(4) . . . . ?
C19 C15 N16 C17 -0.2(4) . . . . ?
F20 B5 N6 N2 110.6(3) . . . . ?
F20 B5 N6 C7 -71.5(4) . . . . ?
F21 B5 N6 N2 -123.2(3) . . . . ?
F21 B5 N6 C7 54.8(4) . . . . ?
C22 C9 C10 C11 -179.5(4) . . . . ?
C23 C11 N12 B1 -4.3(5) . . . . ?
C23 C11 N12 C8 -179.1(3) . . . . ?


_olex2_submission_original_sample_id WDH-SD-38
_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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.587
####################################################################### 
# 
# 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_wdh1098
_database_code_depnum_ccdc_archive 'CCDC 1982534'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-18
_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         'C12 H11 B2 F4 N3 O2'
_chemical_formula_sum            'C12 H11 B2 F4 N3 O2'
_chemical_formula_weight         326.86
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H11 B2 F4 N3 O2'
_chemical_oxdiff_usercomment     JK021
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   23.9330(10)
_cell_length_b                   12.5943(6)
_cell_length_c                   4.7440(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1429.93(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0740
_cell_measurement_theta_min      3.0200
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46642
_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    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.5
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8443
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.023
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  92.00   1.00   60.00    --   18.87  19.00   0.00  117
  2  ω    -50.00  40.00   1.00   60.00    --   18.87 -57.00-180.00   90
  3  ω    -87.00 -46.00   1.00   60.00    --  -17.07 -77.00 150.00   41
  4  ω     34.00  95.00   1.00   60.00    --   18.87-178.00  60.00   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      0.0276651000
_diffrn_orient_matrix_UB_12      0.0153259000
_diffrn_orient_matrix_UB_13      -0.0348029000
_diffrn_orient_matrix_UB_21      -0.0091392000
_diffrn_orient_matrix_UB_22      0.0530319000
_diffrn_orient_matrix_UB_23      -0.0202842000
_diffrn_orient_matrix_UB_31      0.0054126000
_diffrn_orient_matrix_UB_32      0.0111969000
_diffrn_orient_matrix_UB_33      0.1439826000
_diffrn_oxdiff_ac4_digest_frames 
;
0141da7c765bba9ad1a2920f72bfe22929000276d90
;
_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         0.724
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                2241
_reflns_number_total             2817
_reflns_odcompleteness_completeness 99.72
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 754 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.062
_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)+(0.0429P)²+0.2150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0990
_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:
 C7(H7), C10(H10), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_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
B1 B 0.66070(14) 0.3407(3) 0.7141(9) 0.0415(9) Uani 1 1 d . . . . .
N2 N 0.60227(10) 0.31497(19) 0.5608(6) 0.0384(6) Uani 1 1 d . . . . .
C3 C 0.57334(13) 0.2265(3) 0.5553(8) 0.0444(8) Uani 1 1 d . . . . .
N12 N 0.67126(10) 0.4586(2) 0.6659(7) 0.0469(7) Uani 1 1 d . . . . .
O4 O 0.52698(9) 0.22883(18) 0.4094(6) 0.0548(7) Uani 1 1 d . . . . .
B5 B 0.51754(15) 0.3368(3) 0.2895(9) 0.0438(9) Uani 1 1 d . . . . .
N6 N 0.57175(9) 0.3900(2) 0.4050(6) 0.0399(6) Uani 1 1 d . . . . .
C7 C 0.58988(12) 0.4874(2) 0.3787(8) 0.0440(8) Uani 1 1 d . . . . .
H7 H 0.568696 0.534457 0.272059 0.053 Uiso 1 1 calc R . . . .
C8 C 0.63848(13) 0.5245(3) 0.4992(8) 0.0469(8) Uani 1 1 d . . . . .
C9 C 0.66181(15) 0.6273(3) 0.4980(10) 0.0590(10) Uani 1 1 d . . . . .
C10 C 0.70861(16) 0.6216(3) 0.6684(11) 0.0697(12) Uani 1 1 d . . . . .
H10 H 0.732883 0.677338 0.707687 0.084 Uiso 1 1 calc R . . . .
C11 C 0.71330(14) 0.5185(3) 0.7711(9) 0.0595(10) Uani 1 1 d . . . . .
F13 F 0.65505(8) 0.31753(17) 0.9940(4) 0.0604(6) Uani 1 1 d . . . . .
F14 F 0.70124(7) 0.27804(15) 0.5944(5) 0.0570(6) Uani 1 1 d . . . . .
C15 C 0.58805(14) 0.1289(3) 0.6953(9) 0.0557(10) Uani 1 1 d . . . . .
O16 O 0.54991(13) 0.0502(2) 0.6549(10) 0.0963(13) Uani 1 1 d . . . . .
C17 C 0.5699(2) -0.0342(4) 0.8074(18) 0.111(2) Uani 1 1 d . . . . .
H17 H 0.551836 -0.099358 0.821762 0.133 Uiso 1 1 calc R . . . .
C18 C 0.6166(2) -0.0121(4) 0.9282(15) 0.1000(19) Uani 1 1 d . . . . .
H18 H 0.637917 -0.057413 1.039718 0.120 Uiso 1 1 calc R . . . .
C19 C 0.62935(16) 0.0947(3) 0.8580(11) 0.0720(13) Uani 1 1 d . . . . .
H19 H 0.660531 0.133175 0.914994 0.086 Uiso 1 1 calc R . . . .
F20 F 0.47026(7) 0.38163(16) 0.3953(5) 0.0579(6) Uani 1 1 d . . . . .
F21 F 0.51588(8) 0.33467(19) 0.0029(5) 0.0642(6) Uani 1 1 d . . . . .
C22 C 0.6387(2) 0.7214(3) 0.3456(14) 0.0895(17) Uani 1 1 d . . . . .
H22A H 0.657626 0.729406 0.168347 0.134 Uiso 1 1 calc GR . . . .
H22B H 0.644212 0.784010 0.457496 0.134 Uiso 1 1 calc GR . . . .
H22C H 0.599513 0.711129 0.312888 0.134 Uiso 1 1 calc GR . . . .
C23 C 0.75625(16) 0.4737(4) 0.9675(12) 0.0868(16) Uani 1 1 d . . . . .
H23A H 0.741275 0.471097 1.155115 0.130 Uiso 1 1 calc GR . . . .
H23B H 0.788902 0.517953 0.965392 0.130 Uiso 1 1 calc GR . . . .
H23C H 0.766089 0.403301 0.907860 0.130 Uiso 1 1 calc GR . . . .


_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
B1 N2 1.609(4) . ?
B1 N12 1.523(5) . ?
B1 F13 1.367(5) . ?
B1 F14 1.373(4) . ?
N2 C3 1.312(4) . ?
N2 N6 1.405(3) . ?
C3 O4 1.308(4) . ?
C3 C15 1.441(5) . ?
N12 C8 1.389(4) . ?
N12 C11 1.353(4) . ?
O4 B5 1.491(5) . ?
B5 N6 1.560(4) . ?
B5 F20 1.361(4) . ?
B5 F21 1.361(5) . ?
N6 C7 1.306(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(4) . ?
C8 C9 1.411(5) . ?
C9 C10 1.383(6) . ?
C9 C22 1.494(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(6) . ?
C11 C23 1.498(6) . ?
C15 O16 1.361(4) . ?
C15 C19 1.326(5) . ?
O16 C17 1.372(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.287(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.419(6) . ?
C19 H19 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
N12 B1 N2 105.8(2) . . ?
F13 B1 N2 108.1(3) . . ?
F13 B1 N12 111.7(3) . . ?
F13 B1 F14 110.4(3) . . ?
F14 B1 N2 108.2(3) . . ?
F14 B1 N12 112.4(3) . . ?
C3 N2 B1 129.7(3) . . ?
C3 N2 N6 106.7(3) . . ?
N6 N2 B1 123.6(2) . . ?
N2 C3 C15 125.9(3) . . ?
O4 C3 N2 116.0(3) . . ?
O4 C3 C15 118.1(3) . . ?
C8 N12 B1 125.0(3) . . ?
C11 N12 B1 127.7(3) . . ?
C11 N12 C8 107.3(3) . . ?
C3 O4 B5 110.6(3) . . ?
O4 B5 N6 97.6(2) . . ?
F20 B5 O4 111.3(3) . . ?
F20 B5 N6 112.6(3) . . ?
F21 B5 O4 111.6(3) . . ?
F21 B5 N6 112.6(3) . . ?
F21 B5 F20 110.6(3) . . ?
N2 N6 B5 109.2(2) . . ?
C7 N6 N2 120.6(3) . . ?
C7 N6 B5 130.2(3) . . ?
N6 C7 H7 118.0 . . ?
N6 C7 C8 124.0(3) . . ?
C8 C7 H7 118.0 . . ?
N12 C8 C9 109.1(3) . . ?
C7 C8 N12 120.7(3) . . ?
C7 C8 C9 130.1(3) . . ?
C8 C9 C22 125.7(4) . . ?
C10 C9 C8 105.7(3) . . ?
C10 C9 C22 128.6(4) . . ?
C9 C10 H10 125.7 . . ?
C9 C10 C11 108.6(3) . . ?
C11 C10 H10 125.7 . . ?
N12 C11 C10 109.4(3) . . ?
N12 C11 C23 122.0(4) . . ?
C10 C11 C23 128.7(4) . . ?
O16 C15 C3 113.1(3) . . ?
C19 C15 C3 136.7(3) . . ?
C19 C15 O16 110.2(3) . . ?
C15 O16 C17 104.8(4) . . ?
O16 C17 H17 124.1 . . ?
C18 C17 O16 111.7(4) . . ?
C18 C17 H17 124.1 . . ?
C17 C18 H18 126.7 . . ?
C17 C18 C19 106.7(5) . . ?
C19 C18 H18 126.7 . . ?
C15 C19 C18 106.5(4) . . ?
C15 C19 H19 126.7 . . ?
C18 C19 H19 126.7 . . ?
C9 C22 H22A 109.5 . . ?
C9 C22 H22B 109.5 . . ?
C9 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
B1 N2 C3 O4 -179.4(3) . . . . ?
B1 N2 C3 C15 0.9(6) . . . . ?
B1 N2 N6 B5 -179.8(3) . . . . ?
B1 N2 N6 C7 -0.5(4) . . . . ?
B1 N12 C8 C7 5.1(5) . . . . ?
B1 N12 C8 C9 -178.3(3) . . . . ?
B1 N12 C11 C10 178.1(3) . . . . ?
B1 N12 C11 C23 -2.0(6) . . . . ?
N2 B1 N12 C8 -5.4(4) . . . . ?
N2 B1 N12 C11 175.1(3) . . . . ?
N2 C3 O4 B5 -1.9(4) . . . . ?
N2 C3 C15 O16 179.4(4) . . . . ?
N2 C3 C15 C19 0.1(8) . . . . ?
N2 N6 C7 C8 -0.7(5) . . . . ?
C3 N2 N6 B5 -0.8(3) . . . . ?
C3 N2 N6 C7 178.5(3) . . . . ?
C3 O4 B5 N6 1.2(3) . . . . ?
C3 O4 B5 F20 -116.7(3) . . . . ?
C3 O4 B5 F21 119.1(3) . . . . ?
C3 C15 O16 C17 -178.4(4) . . . . ?
C3 C15 C19 C18 178.8(5) . . . . ?
N12 B1 N2 C3 -175.5(3) . . . . ?
N12 B1 N2 N6 3.2(4) . . . . ?
N12 C8 C9 C10 -0.5(4) . . . . ?
N12 C8 C9 C22 -179.4(4) . . . . ?
O4 C3 C15 O16 -0.3(5) . . . . ?
O4 C3 C15 C19 -179.6(5) . . . . ?
O4 B5 N6 N2 -0.2(3) . . . . ?
O4 B5 N6 C7 -179.4(3) . . . . ?
B5 N6 C7 C8 178.4(3) . . . . ?
N6 N2 C3 O4 1.7(4) . . . . ?
N6 N2 C3 C15 -178.0(3) . . . . ?
N6 C7 C8 N12 -1.4(6) . . . . ?
N6 C7 C8 C9 -177.2(4) . . . . ?
C7 C8 C9 C10 175.6(4) . . . . ?
C7 C8 C9 C22 -3.3(7) . . . . ?
C8 N12 C11 C10 -1.4(4) . . . . ?
C8 N12 C11 C23 178.4(4) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 N12 1.1(5) . . . . ?
C9 C10 C11 C23 -178.7(4) . . . . ?
C11 N12 C8 C7 -175.4(3) . . . . ?
C11 N12 C8 C9 1.2(4) . . . . ?
F13 B1 N2 C3 -55.7(4) . . . . ?
F13 B1 N2 N6 123.0(3) . . . . ?
F13 B1 N12 C8 -122.8(3) . . . . ?
F13 B1 N12 C11 57.7(4) . . . . ?
F14 B1 N2 C3 63.9(4) . . . . ?
F14 B1 N2 N6 -117.4(3) . . . . ?
F14 B1 N12 C8 112.4(3) . . . . ?
F14 B1 N12 C11 -67.1(5) . . . . ?
C15 C3 O4 B5 177.8(3) . . . . ?
C15 O16 C17 C18 -1.2(8) . . . . ?
O16 C15 C19 C18 -0.5(6) . . . . ?
O16 C17 C18 C19 0.9(8) . . . . ?
C17 C18 C19 C15 -0.2(7) . . . . ?
C19 C15 O16 C17 1.0(6) . . . . ?
F20 B5 N6 N2 116.7(3) . . . . ?
F20 B5 N6 C7 -62.5(5) . . . . ?
F21 B5 N6 N2 -117.4(3) . . . . ?
F21 B5 N6 C7 63.4(5) . . . . ?
C22 C9 C10 C11 178.5(5) . . . . ?


_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 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.423
####################################################################### 
# 
# 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_wdh1097
_database_code_depnum_ccdc_archive 'CCDC 1982533'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-18
_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         'C9 H11 B2 F4 N3 O'
_chemical_formula_sum            'C9 H11 B2 F4 N3 O'
_chemical_formula_weight         274.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H11 B2 F4 N3 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      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                   12.9329(11)
_cell_length_b                   4.8706(4)
_cell_length_c                   19.777(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.631(9)
_cell_angle_gamma                90
_cell_volume                     1210.71(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3329
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2010
_cell_measurement_theta_min      3.2240
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70968
_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    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3570
_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         26.368
_diffrn_reflns_theta_min         2.956
_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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00   30.00    --  -17.15 -99.00 150.00   45
  2  ω    -54.00  63.00   1.00   30.00    --   18.87 -19.00  90.00  117
  3  ω    -51.00  49.00   1.00   30.00    --   18.87 -77.00  60.00  100
  4  ω    -43.00  55.00   1.00   30.00    --  -17.15  38.00 -60.00   98
  5  ω    -20.00  25.00   1.00   30.00    --  -17.15 -99.00   0.00   45
  6  ω    -20.00  51.00   1.00   30.00    --   18.87 -99.00 -30.00   71
  7  ω    -11.00  89.00   1.00   30.00    --   18.87  77.00-180.00  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      -0.0105325000
_diffrn_orient_matrix_UB_12      0.0177697000
_diffrn_orient_matrix_UB_13      -0.0366051000
_diffrn_orient_matrix_UB_21      -0.0156784000
_diffrn_orient_matrix_UB_22      -0.1395282000
_diffrn_orient_matrix_UB_23      -0.0048259000
_diffrn_orient_matrix_UB_31      -0.0531584000
_diffrn_orient_matrix_UB_32      0.0375947000
_diffrn_orient_matrix_UB_33      -0.0005592000
_diffrn_oxdiff_ac4_digest_frames 
;
0129674fd9da3158ce678e97e4040efb310002737fd
;
_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                2622
_reflns_number_total             3570
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_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         0.203
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.039
_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)+(0.0784P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4839(17)
 0.5161(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_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
B1 B 0.1554(2) 0.5305(6) 0.67993(17) 0.0392(7) Uani 1 1 d . . . . .
N2 N 0.23050(15) 0.6999(4) 0.74164(10) 0.0364(5) Uani 1 1 d . . . . .
C3 C 0.2194(2) 0.7319(6) 0.80518(16) 0.0481(7) Uani 1 1 d . . . . .
O4 O 0.29107(16) 0.8767(5) 0.84623(10) 0.0585(6) Uani 1 1 d . . . . .
B5 B 0.3744(3) 0.9706(7) 0.80940(17) 0.0456(8) Uani 1 1 d . . . . .
N6 N 0.32214(15) 0.8439(4) 0.73652(11) 0.0381(5) Uani 1 1 d . . . . .
C7 C 0.3505(2) 0.8472(6) 0.67772(14) 0.0404(7) Uani 1 1 d . . . . .
H7 H 0.410293 0.949372 0.675279 0.048 Uiso 1 1 calc R . . . .
C8 C 0.29763(19) 0.7085(5) 0.61830(14) 0.0388(6) Uani 1 1 d . . . . .
C9 C 0.3213(2) 0.6865(6) 0.55293(14) 0.0472(7) Uani 1 1 d . . . . .
C10 C 0.2473(2) 0.5057(7) 0.51548(15) 0.0528(8) Uani 1 1 d . . . . .
H10 H 0.242859 0.450885 0.469832 0.063 Uiso 1 1 calc R . . . .
C11 C 0.1807(2) 0.4190(6) 0.55691(14) 0.0451(7) Uani 1 1 d . . . . .
N12 N 0.21014(16) 0.5433(4) 0.61996(11) 0.0394(5) Uani 1 1 d . . . . .
F13 F 0.14735(13) 0.2653(3) 0.70279(8) 0.0541(5) Uani 1 1 d . . . . .
F14 F 0.05684(11) 0.6520(3) 0.66361(8) 0.0540(5) Uani 1 1 d . . . . .
C15 C 0.1303(3) 0.6119(8) 0.83097(17) 0.0714(10) Uani 1 1 d . . . . .
H15A H 0.087360 0.499419 0.795300 0.107 Uiso 1 1 calc GR . . . .
H15B H 0.087519 0.756922 0.842880 0.107 Uiso 1 1 calc GR . . . .
H15C H 0.158396 0.501894 0.871399 0.107 Uiso 1 1 calc GR . . . .
F16 F 0.47032(12) 0.8540(4) 0.83837(9) 0.0622(5) Uani 1 1 d . . . . .
F17 F 0.38164(15) 1.2465(4) 0.80804(9) 0.0675(6) Uani 1 1 d . . . . .
C18 C 0.4106(2) 0.8264(7) 0.52985(17) 0.0659(9) Uani 1 1 d . . . . .
H18A H 0.411365 1.017883 0.541438 0.099 Uiso 1 1 calc GR . . . .
H18B H 0.400530 0.806295 0.480435 0.099 Uiso 1 1 calc GR . . . .
H18C H 0.477084 0.744377 0.552926 0.099 Uiso 1 1 calc GR . . . .
C19 C 0.0907(2) 0.2199(7) 0.53993(16) 0.0616(9) Uani 1 1 d . . . . .
H19A H 0.112120 0.049062 0.563248 0.092 Uiso 1 1 calc GR . . . .
H19B H 0.071058 0.189799 0.490581 0.092 Uiso 1 1 calc GR . . . .
H19C H 0.030881 0.292669 0.555025 0.092 Uiso 1 1 calc GR . . . .


_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
B1 N2 1.598(4) . ?
B1 N12 1.519(4) . ?
B1 F13 1.380(3) . ?
B1 F14 1.373(3) . ?
N2 C3 1.307(3) . ?
N2 N6 1.401(3) . ?
C3 O4 1.289(3) . ?
C3 C15 1.486(4) . ?
O4 B5 1.507(4) . ?
B5 N6 1.567(4) . ?
B5 F16 1.362(3) . ?
B5 F17 1.348(4) . ?
N6 C7 1.300(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(3) . ?
C8 C9 1.401(4) . ?
C8 N12 1.395(3) . ?
C9 C10 1.380(4) . ?
C9 C18 1.502(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(4) . ?
C11 N12 1.358(3) . ?
C11 C19 1.492(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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
N12 B1 N2 105.3(2) . . ?
F13 B1 N2 108.2(2) . . ?
F13 B1 N12 112.3(2) . . ?
F14 B1 N2 108.7(2) . . ?
F14 B1 N12 112.1(2) . . ?
F14 B1 F13 110.0(2) . . ?
C3 N2 B1 127.7(2) . . ?
C3 N2 N6 107.2(2) . . ?
N6 N2 B1 125.1(2) . . ?
N2 C3 C15 123.6(3) . . ?
O4 C3 N2 116.4(3) . . ?
O4 C3 C15 120.0(3) . . ?
C3 O4 B5 110.6(2) . . ?
O4 B5 N6 97.0(2) . . ?
F16 B5 O4 110.8(2) . . ?
F16 B5 N6 112.1(3) . . ?
F17 B5 O4 111.9(3) . . ?
F17 B5 N6 113.0(2) . . ?
F17 B5 F16 111.3(3) . . ?
N2 N6 B5 108.6(2) . . ?
C7 N6 N2 119.5(2) . . ?
C7 N6 B5 131.8(2) . . ?
N6 C7 H7 117.8 . . ?
N6 C7 C8 124.4(2) . . ?
C8 C7 H7 117.8 . . ?
C7 C8 C9 130.3(2) . . ?
C7 C8 N12 120.1(2) . . ?
N12 C8 C9 109.4(2) . . ?
C8 C9 C18 126.6(3) . . ?
C10 C9 C8 105.6(2) . . ?
C10 C9 C18 127.7(3) . . ?
C9 C10 H10 125.5 . . ?
C9 C10 C11 109.0(3) . . ?
C11 C10 H10 125.5 . . ?
C10 C11 C19 128.7(3) . . ?
N12 C11 C10 109.2(2) . . ?
N12 C11 C19 122.1(3) . . ?
C8 N12 B1 124.9(2) . . ?
C11 N12 B1 128.1(2) . . ?
C11 N12 C8 106.8(2) . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
C11 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
B1 N2 C3 O4 179.4(2) . . . . ?
B1 N2 C3 C15 -0.6(5) . . . . ?
B1 N2 N6 B5 -177.7(2) . . . . ?
B1 N2 N6 C7 0.7(4) . . . . ?
N2 B1 N12 C8 -9.3(3) . . . . ?
N2 B1 N12 C11 176.3(2) . . . . ?
N2 C3 O4 B5 -1.4(4) . . . . ?
N2 N6 C7 C8 -2.1(4) . . . . ?
C3 N2 N6 B5 2.3(3) . . . . ?
C3 N2 N6 C7 -179.3(2) . . . . ?
C3 O4 B5 N6 2.5(3) . . . . ?
C3 O4 B5 F16 -114.3(3) . . . . ?
C3 O4 B5 F17 120.8(3) . . . . ?
O4 B5 N6 N2 -2.8(3) . . . . ?
O4 B5 N6 C7 179.0(3) . . . . ?
B5 N6 C7 C8 175.9(3) . . . . ?
N6 N2 C3 O4 -0.6(3) . . . . ?
N6 N2 C3 C15 179.3(3) . . . . ?
N6 C7 C8 C9 -177.5(3) . . . . ?
N6 C7 C8 N12 -2.6(4) . . . . ?
C7 C8 C9 C10 175.1(3) . . . . ?
C7 C8 C9 C18 -3.5(5) . . . . ?
C7 C8 N12 B1 9.3(4) . . . . ?
C7 C8 N12 C11 -175.3(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C8 N12 B1 -174.9(2) . . . . ?
C9 C8 N12 C11 0.6(3) . . . . ?
C9 C10 C11 N12 0.6(3) . . . . ?
C9 C10 C11 C19 -178.5(3) . . . . ?
C10 C11 N12 B1 174.5(2) . . . . ?
C10 C11 N12 C8 -0.7(3) . . . . ?
N12 B1 N2 C3 -175.6(2) . . . . ?
N12 B1 N2 N6 4.5(3) . . . . ?
N12 C8 C9 C10 -0.2(3) . . . . ?
N12 C8 C9 C18 -178.8(3) . . . . ?
F13 B1 N2 C3 -55.3(3) . . . . ?
F13 B1 N2 N6 124.7(2) . . . . ?
F13 B1 N12 C8 -126.8(2) . . . . ?
F13 B1 N12 C11 58.8(4) . . . . ?
F14 B1 N2 C3 64.1(3) . . . . ?
F14 B1 N2 N6 -115.8(2) . . . . ?
F14 B1 N12 C8 108.7(3) . . . . ?
F14 B1 N12 C11 -65.7(3) . . . . ?
C15 C3 O4 B5 178.6(3) . . . . ?
F16 B5 N6 N2 113.0(3) . . . . ?
F16 B5 N6 C7 -65.2(4) . . . . ?
F17 B5 N6 N2 -120.3(3) . . . . ?
F17 B5 N6 C7 61.6(4) . . . . ?
C18 C9 C10 C11 178.3(3) . . . . ?
C19 C11 N12 B1 -6.3(4) . . . . ?
C19 C11 N12 C8 178.5(2) . . . . ?


_olex2_submission_original_sample_id JK014-2
_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 2.179
_oxdiff_exptl_absorpt_empirical_full_min 0.412
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4839(17)
2 0.5161(17)

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

data_wdh1095
_database_code_depnum_ccdc_archive 'CCDC 1982535'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-04-13 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         'C14 H16 B2 F4 N4 O'
_chemical_formula_sum            'C14 H16 B2 F4 N4 O'
_chemical_formula_weight         353.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H16 B2 F4 N4 O1'
_chemical_oxdiff_usercomment     'JK 25-2'
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                   8.1042(6)
_cell_length_b                   9.7049(9)
_cell_length_c                   10.4691(10)
_cell_angle_alpha                80.218(8)
_cell_angle_beta                 86.082(8)
_cell_angle_gamma                87.104(7)
_cell_volume                     808.89(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6480
_cell_measurement_theta_min      3.0770
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54735
_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    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15627
_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         2.521
_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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00    4.00    --  -17.15 -99.00 -90.00   45
  2  ω    -93.00 -35.00   1.00    4.00    --  -17.15-178.00  60.00   58
  3  ω    -20.00  25.00   1.00    4.00    --  -17.15 -99.00 120.00   45
  4  ω     -7.00  91.00   1.00    4.00    --   18.87  38.00 120.00   98
  5  ω     -7.00  91.00   1.00    4.00    --   18.87  38.00 -90.00   98
  6  ω    -54.00  44.00   1.00    4.00    --   18.87 -38.00 -60.00   98
  7  ω    -93.00 -35.00   1.00    4.00    --  -17.15-178.00 -30.00   58
  8  ω     34.00  95.00   1.00    4.00    --   18.87-178.00 -30.00   61
  9  ω    -20.00  61.00   1.00    4.00    --   18.87 -99.00 120.00   81
 10  ω    -20.00  61.00   1.00    4.00    --   18.87 -99.00 -90.00   81
 11  ω     -3.00  88.00   1.00    4.00    --   18.87  57.00   0.00   91
 12  ω    -47.00  53.00   1.00    4.00    --  -17.15  77.00 -30.00  100
 13  ω    -54.00  63.00   1.00    4.00    --   18.87 -19.00  90.00  117
;
_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      0.0128605000
_diffrn_orient_matrix_UB_12      0.0693885000
_diffrn_orient_matrix_UB_13      0.0089771000
_diffrn_orient_matrix_UB_21      -0.0650860000
_diffrn_orient_matrix_UB_22      0.0250082000
_diffrn_orient_matrix_UB_23      -0.0409017000
_diffrn_orient_matrix_UB_31      -0.0575033000
_diffrn_orient_matrix_UB_32      -0.0083029000
_diffrn_orient_matrix_UB_33      0.0546876000
_diffrn_oxdiff_ac4_digest_frames 
;
019cfd154a99f9d215a897fc61627c5b8e000281fa2
;
_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                2467
_reflns_number_total             3289
_reflns_odcompleteness_completeness 99.91
_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         0.235
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.039
_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)+(0.0523P)²+0.2914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1332
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23a,H23b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C24(H24a,H24b,H24c), C25(H25a,H25b,H25c)
;
_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
F13 F 0.29862(18) 0.05068(13) 0.72397(13) 0.0689(4) Uani 1 1 d . . . . .
F14 F 0.14219(15) 0.22572(17) 0.61637(12) 0.0707(4) Uani 1 1 d . . . . .
F20 F 0.36363(17) 0.31787(17) 1.10512(12) 0.0724(4) Uani 1 1 d . . . . .
F21 F 0.25491(17) 0.51559(14) 0.99435(14) 0.0711(4) Uani 1 1 d . . . . .
O4 O 0.11363(17) 0.30621(15) 1.00529(13) 0.0504(4) Uani 1 1 d . . . . .
N2 N 0.23664(18) 0.25584(16) 0.82150(14) 0.0391(4) Uani 1 1 d . . . . .
N6 N 0.35070(18) 0.33330(16) 0.87246(14) 0.0401(4) Uani 1 1 d . . . . .
N12 N 0.43051(19) 0.26196(17) 0.62464(14) 0.0419(4) Uani 1 1 d . . . . .
N16 N -0.1694(2) 0.1779(2) 0.9899(2) 0.0626(5) Uani 1 1 d . . . . .
C3 C 0.1048(2) 0.24281(19) 0.90523(18) 0.0406(4) Uani 1 1 d . . . . .
C7 C 0.4880(2) 0.37151(19) 0.80452(18) 0.0411(4) Uani 1 1 d . . . . .
H7 H 0.560020 0.423327 0.841010 0.049 Uiso 1 1 calc R . . . .
C8 C 0.5328(2) 0.34031(19) 0.68316(18) 0.0405(4) Uani 1 1 d . . . . .
C9 C 0.6700(2) 0.3804(2) 0.59717(19) 0.0461(5) Uani 1 1 d . . . . .
C10 C 0.6487(3) 0.3266(2) 0.4853(2) 0.0506(5) Uani 1 1 d . . . . .
C11 C 0.5017(2) 0.2531(2) 0.50472(18) 0.0483(5) Uani 1 1 d . . . . .
C15 C -0.0414(2) 0.1695(2) 0.89847(19) 0.0436(4) Uani 1 1 d . . . . .
C17 C -0.2923(3) 0.0977(3) 0.9672(3) 0.0672(7) Uani 1 1 d . . . . .
H17 H -0.392604 0.085477 1.015617 0.081 Uiso 1 1 calc R . . . .
C18 C -0.2448(3) 0.0384(3) 0.8625(3) 0.0711(7) Uani 1 1 d . . . . .
H18 H -0.306503 -0.021846 0.826345 0.085 Uiso 1 1 calc R . . . .
C19 C -0.0873(3) 0.0827(2) 0.8176(2) 0.0565(6) Uani 1 1 d . . . . .
H19 H -0.025089 0.058162 0.746345 0.068 Uiso 1 1 calc R . . . .
C22 C 0.8081(3) 0.4649(2) 0.6252(2) 0.0609(6) Uani 1 1 d . . . . .
H22A H 0.783255 0.495961 0.706902 0.091 Uiso 1 1 calc GR . . . .
H22B H 0.820794 0.544527 0.557580 0.091 Uiso 1 1 calc GR . . . .
H22C H 0.908904 0.408381 0.629079 0.091 Uiso 1 1 calc GR . . . .
C23 C 0.7609(3) 0.3432(3) 0.3629(2) 0.0674(7) Uani 1 1 d . . . . .
H23A H 0.694407 0.344060 0.289112 0.081 Uiso 1 1 calc R . . . .
H23B H 0.812488 0.432856 0.351995 0.081 Uiso 1 1 calc R . . . .
C24 C 0.8945(3) 0.2292(3) 0.3627(3) 0.0716(7) Uani 1 1 d . . . . .
H24A H 0.962394 0.246709 0.283368 0.107 Uiso 1 1 calc GR . . . .
H24B H 0.844513 0.140450 0.369686 0.107 Uiso 1 1 calc GR . . . .
H24C H 0.961455 0.228016 0.435123 0.107 Uiso 1 1 calc GR . . . .
C25 C 0.4251(3) 0.1762(3) 0.4128(2) 0.0633(6) Uani 1 1 d . . . . .
H25A H 0.354023 0.107020 0.460980 0.095 Uiso 1 1 calc GR . . . .
H25B H 0.510677 0.131209 0.364703 0.095 Uiso 1 1 calc GR . . . .
H25C H 0.361573 0.241088 0.353835 0.095 Uiso 1 1 calc GR . . . .
B1 B 0.2759(3) 0.1933(2) 0.6915(2) 0.0447(5) Uani 1 1 d . . . . .
B5 B 0.2742(3) 0.3735(3) 1.0020(2) 0.0470(5) Uani 1 1 d . . . . .
H16 H -0.167(4) 0.234(4) 1.066(4) 0.128(12) 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
F13 B1 1.374(3) . ?
F14 B1 1.375(3) . ?
F20 B5 1.361(3) . ?
F21 B5 1.369(3) . ?
O4 C3 1.310(2) . ?
O4 B5 1.481(3) . ?
N2 N6 1.4064(19) . ?
N2 C3 1.332(2) . ?
N2 B1 1.589(2) . ?
N6 C7 1.314(2) . ?
N6 B5 1.555(2) . ?
N12 C8 1.390(2) . ?
N12 C11 1.360(2) . ?
N12 B1 1.520(3) . ?
N16 C15 1.371(3) . ?
N16 C17 1.352(3) . ?
N16 H16 1.05(3) . ?
C3 C15 1.424(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(2) . ?
C8 C9 1.409(3) . ?
C9 C10 1.384(3) . ?
C9 C22 1.493(3) . ?
C10 C11 1.404(3) . ?
C10 C23 1.511(3) . ?
C11 C25 1.497(3) . ?
C15 C19 1.372(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.348(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.392(3) . ?
C19 H19 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.508(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C3 O4 B5 111.41(14) . . ?
N6 N2 B1 122.71(14) . . ?
C3 N2 N6 106.91(13) . . ?
C3 N2 B1 130.29(15) . . ?
N2 N6 B5 108.96(14) . . ?
C7 N6 N2 120.08(14) . . ?
C7 N6 B5 130.56(15) . . ?
C8 N12 B1 124.11(15) . . ?
C11 N12 C8 107.08(16) . . ?
C11 N12 B1 128.68(16) . . ?
C15 N16 H16 124.2(19) . . ?
C17 N16 C15 108.95(19) . . ?
C17 N16 H16 126.8(19) . . ?
O4 C3 N2 114.63(15) . . ?
O4 C3 C15 117.30(16) . . ?
N2 C3 C15 128.07(16) . . ?
N6 C7 H7 117.7 . . ?
N6 C7 C8 124.64(17) . . ?
C8 C7 H7 117.7 . . ?
N12 C8 C9 109.21(16) . . ?
C7 C8 N12 120.07(16) . . ?
C7 C8 C9 130.66(17) . . ?
C8 C9 C22 125.24(18) . . ?
C10 C9 C8 106.40(17) . . ?
C10 C9 C22 128.36(18) . . ?
C9 C10 C11 107.80(17) . . ?
C9 C10 C23 127.0(2) . . ?
C11 C10 C23 125.2(2) . . ?
N12 C11 C10 109.50(17) . . ?
N12 C11 C25 122.15(19) . . ?
C10 C11 C25 128.35(18) . . ?
N16 C15 C3 119.02(17) . . ?
N16 C15 C19 107.37(18) . . ?
C19 C15 C3 133.58(18) . . ?
N16 C17 H17 125.8 . . ?
C18 C17 N16 108.4(2) . . ?
C18 C17 H17 125.8 . . ?
C17 C18 H18 125.9 . . ?
C17 C18 C19 108.2(2) . . ?
C19 C18 H18 125.9 . . ?
C15 C19 C18 107.0(2) . . ?
C15 C19 H19 126.5 . . ?
C18 C19 H19 126.5 . . ?
C9 C22 H22A 109.5 . . ?
C9 C22 H22B 109.5 . . ?
C9 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 108.8 . . ?
C10 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C10 113.6(2) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C25 H25A 109.5 . . ?
C11 C25 H25B 109.5 . . ?
C11 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F13 B1 F14 110.31(17) . . ?
F13 B1 N2 108.24(17) . . ?
F13 B1 N12 112.17(17) . . ?
F14 B1 N2 107.71(16) . . ?
F14 B1 N12 111.22(18) . . ?
N12 B1 N2 106.98(14) . . ?
F20 B5 F21 110.26(17) . . ?
F20 B5 O4 112.12(18) . . ?
F20 B5 N6 112.32(18) . . ?
F21 B5 O4 112.08(18) . . ?
F21 B5 N6 111.54(18) . . ?
O4 B5 N6 98.05(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C3 C15 N16 5.1(3) . . . . ?
O4 C3 C15 C19 -172.9(2) . . . . ?
N2 N6 C7 C8 -0.6(3) . . . . ?
N2 N6 B5 F20 118.13(18) . . . . ?
N2 N6 B5 F21 -117.49(18) . . . . ?
N2 N6 B5 O4 0.1(2) . . . . ?
N2 C3 C15 N16 -174.9(2) . . . . ?
N2 C3 C15 C19 7.1(4) . . . . ?
N6 N2 C3 O4 2.1(2) . . . . ?
N6 N2 C3 C15 -177.97(19) . . . . ?
N6 N2 B1 F13 107.86(19) . . . . ?
N6 N2 B1 F14 -132.87(18) . . . . ?
N6 N2 B1 N12 -13.2(2) . . . . ?
N6 C7 C8 N12 -0.6(3) . . . . ?
N6 C7 C8 C9 176.1(2) . . . . ?
N12 C8 C9 C10 0.6(2) . . . . ?
N12 C8 C9 C22 -179.62(19) . . . . ?
N16 C15 C19 C18 -0.3(3) . . . . ?
N16 C17 C18 C19 -0.1(3) . . . . ?
C3 O4 B5 F20 -117.09(19) . . . . ?
C3 O4 B5 F21 118.27(18) . . . . ?
C3 O4 B5 N6 1.0(2) . . . . ?
C3 N2 N6 C7 -174.69(17) . . . . ?
C3 N2 N6 B5 -1.2(2) . . . . ?
C3 N2 B1 F13 -68.2(3) . . . . ?
C3 N2 B1 F14 51.1(3) . . . . ?
C3 N2 B1 N12 170.76(18) . . . . ?
C3 C15 C19 C18 177.8(2) . . . . ?
C7 N6 B5 F20 -69.3(3) . . . . ?
C7 N6 B5 F21 55.0(3) . . . . ?
C7 N6 B5 O4 172.68(19) . . . . ?
C7 C8 C9 C10 -176.4(2) . . . . ?
C7 C8 C9 C22 3.4(3) . . . . ?
C8 N12 C11 C10 -0.6(2) . . . . ?
C8 N12 C11 C25 -179.77(19) . . . . ?
C8 N12 B1 F13 -106.3(2) . . . . ?
C8 N12 B1 F14 129.60(19) . . . . ?
C8 N12 B1 N2 12.2(3) . . . . ?
C8 C9 C10 C11 -1.0(2) . . . . ?
C8 C9 C10 C23 178.7(2) . . . . ?
C9 C10 C11 N12 1.0(2) . . . . ?
C9 C10 C11 C25 -179.9(2) . . . . ?
C9 C10 C23 C24 90.1(3) . . . . ?
C11 N12 C8 C7 177.33(18) . . . . ?
C11 N12 C8 C9 0.0(2) . . . . ?
C11 N12 B1 F13 68.9(3) . . . . ?
C11 N12 B1 F14 -55.1(3) . . . . ?
C11 N12 B1 N2 -172.51(18) . . . . ?
C11 C10 C23 C24 -90.3(3) . . . . ?
C15 N16 C17 C18 -0.1(3) . . . . ?
C17 N16 C15 C3 -178.2(2) . . . . ?
C17 N16 C15 C19 0.3(3) . . . . ?
C17 C18 C19 C15 0.3(3) . . . . ?
C22 C9 C10 C11 179.3(2) . . . . ?
C22 C9 C10 C23 -1.0(4) . . . . ?
C23 C10 C11 N12 -178.7(2) . . . . ?
C23 C10 C11 C25 0.4(4) . . . . ?
B1 N2 N6 C7 8.5(3) . . . . ?
B1 N2 N6 B5 -178.08(17) . . . . ?
B1 N2 C3 O4 178.56(18) . . . . ?
B1 N2 C3 C15 -1.5(3) . . . . ?
B1 N12 C8 C7 -6.5(3) . . . . ?
B1 N12 C8 C9 176.09(17) . . . . ?
B1 N12 C11 C10 -176.46(19) . . . . ?
B1 N12 C11 C25 4.3(3) . . . . ?
B5 O4 C3 N2 -2.0(2) . . . . ?
B5 O4 C3 C15 177.98(18) . . . . ?
B5 N6 C7 C8 -172.4(2) . . . . ?


_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 2.528
_oxdiff_exptl_absorpt_empirical_full_min 0.513
