# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_acb160009_sa
_database_code_depnum_ccdc_archive 'CCDC 2091629'
loop_
_audit_author_name
_audit_author_address
'Paul Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2016-03-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Cl2, C26 H28 B F2 N3'
_chemical_formula_sum            'C27 H30 B Cl2 F2 N3'
_chemical_formula_weight         516.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H30 B1 Cl2 F2 N3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   11.0740(7)
_cell_length_b                   11.1150(6)
_cell_length_c                   12.1059(9)
_cell_angle_alpha                85.621(5)
_cell_angle_beta                 75.257(6)
_cell_angle_gamma                61.941(6)
_cell_volume                     1270.01(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.6370
_cell_measurement_theta_min      3.7550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.596
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0168
0 0 -1 0.0288
1 1 0 0.1067
-1 -1 0 0.0607
1 2 -1 0.1050
-1 0 0 0.2302
1 0 0 0.1382

_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0004 -0.0003 1.0002 0.1234 -0.0022 0.0462
-0.0004 0.0003 -1.0002 -0.1234 0.0022 -0.0462
1.0002 1.0002 -0.0006 0.0240 0.0537 -0.1544
-1.0002 -1.0002 0.0006 -0.0240 -0.0537 0.1544
0.9998 2.0003 -1.0005 -0.0784 0.2096 -0.2265
-1.0002 -0.0003 0.0009 -0.0031 0.0999 0.1284
1.0002 0.0003 -0.0009 0.0031 -0.0999 -0.1284

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18190
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.936
_diffrn_reflns_theta_min         3.781
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -18.00   1.00    1.00    --  -41.59 125.00-120.00   81
  2  ω     15.00 117.00   1.00    1.00    --   41.59  38.00-150.00  102
  3  ω      8.00 120.00   1.00    1.00    --   41.59  77.00  90.00  112
  4  ω     -3.00  96.00   1.00    1.00    --   41.59-125.00   0.00   99
  5  ω      9.00 133.00   1.00    4.00    --   93.50 -93.00-167.58  124
  6  ω      9.00 133.00   1.00    4.00    --   93.50 -93.00  78.60  124
  7  ω      9.00 133.00   1.00    4.00    --   93.50 -93.00 -74.89  124
  8  ω      9.00 133.00   1.00    4.00    --   93.50 -93.00 127.80  124
  9  ω      9.00 133.00   1.00    4.00    --   93.50 -93.00  -1.63  124
 10  ω      4.00 178.00   1.00    4.00    --   93.50   0.00-120.00  174
 11  ω     63.00 168.00   1.00    4.00    --   93.50  61.00  60.00  105
 12  ω     63.00 168.00   1.00    4.00    --   93.50  61.00 120.00  105
 13  ω     66.00 168.00   1.00    4.00    --   93.50  45.00  60.00  102
 14  ω     16.00 119.00   1.00    4.00    --   93.50 -30.00 150.00  103
 15  ω     74.00 100.00   1.00    4.00    --   93.50 -91.00-119.74   26
 16  ω     66.00 146.00   1.00    4.00    --   93.50  61.00 150.00   80
 17  ω     19.00  55.00   1.00    4.00    --   93.50 -45.00 -30.00   36
 18  ω     96.00 121.00   1.00    4.00    --   93.50 -45.00 -30.00   25
 19  ω     64.00 123.00   1.00    4.00    --   93.50 -61.00-180.00   59
 20  ω     19.00  84.00   1.00    4.00    --   93.50-125.00   0.00   65
 21  ω     66.00 123.00   1.00    4.00    --   93.50 -61.00  60.00   57
 22  ω     91.00 139.00   1.00    4.00    --   93.50 125.00  60.00   48
 23  ω     38.00  81.00   1.00    4.00    --   93.50 -94.00-150.00   43
 24  ω     16.00  48.00   1.00    4.00    --   93.50 -94.00-120.00   32
 25  ω     60.00 123.00   1.00    4.00    --   93.50 -93.00  58.58   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0031970000
_diffrn_orient_matrix_UB_12      0.0208993000
_diffrn_orient_matrix_UB_13      0.1233685000
_diffrn_orient_matrix_UB_21      -0.0999758000
_diffrn_orient_matrix_UB_22      0.1536990000
_diffrn_orient_matrix_UB_23      -0.0021254000
_diffrn_orient_matrix_UB_31      -0.1283772000
_diffrn_orient_matrix_UB_32      -0.0259353000
_diffrn_orient_matrix_UB_33      0.0462213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3431
_reflns_number_total             4498
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0497
_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)+(0.0359P)²+1.0447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1251
_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:
 C12(H12A,H12B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17), C21(H21)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.16140(8) 0.18456(8) 0.84554(7) 0.0528(2) Uani 1 1 d . . . . .
Cl2 Cl 0.44985(11) 0.05337(11) 0.87349(9) 0.0757(3) Uani 1 1 d . . . . .
F1 F 0.2918(3) 0.95177(19) 0.61908(17) 0.0709(6) Uani 1 1 d . . . . .
F2 F 0.47435(18) 0.83848(18) 0.4677(2) 0.0656(6) Uani 1 1 d . . . . .
N1 N 0.2636(2) 1.0243(2) 0.43220(18) 0.0330(5) Uani 1 1 d . . . . .
N2 N 0.2690(2) 0.8046(2) 0.49887(17) 0.0273(4) Uani 1 1 d . . . . .
N3 N 0.7917(2) 0.3541(2) 0.98548(19) 0.0362(5) Uani 1 1 d . . . . .
C1 C 0.1527(2) 0.7073(2) 0.4394(2) 0.0285(5) Uani 1 1 d . . . . .
C2 C 0.2320(2) 0.6184(2) 0.5091(2) 0.0284(5) Uani 1 1 d . . . . .
C3 C 0.3024(2) 0.6821(2) 0.5474(2) 0.0280(5) Uani 1 1 d . . . . .
C5 C 0.2876(3) 1.1344(3) 0.4160(2) 0.0389(6) Uani 1 1 d . . . . .
H5 H 0.3495 1.1489 0.4485 0.047 Uiso 1 1 calc R . . . .
C6 C 0.2081(3) 1.2218(3) 0.3452(2) 0.0419(6) Uani 1 1 d . . . . .
H6 H 0.2055 1.3061 0.3209 0.050 Uiso 1 1 calc R . . . .
C7 C 0.1326(3) 1.1637(3) 0.3161(2) 0.0398(6) Uani 1 1 d . . . . .
H7 H 0.0691 1.2007 0.2680 0.048 Uiso 1 1 calc R . . . .
C8 C 0.1248(3) 0.9398(3) 0.3723(2) 0.0311(5) Uani 1 1 d . . . . .
H8 H 0.0583 0.9520 0.3305 0.037 Uiso 1 1 calc R . . . .
C9 C 0.1760(2) 0.8249(2) 0.4322(2) 0.0279(5) Uani 1 1 d . . . . .
C10 C 0.1679(3) 1.0405(3) 0.3709(2) 0.0328(5) Uani 1 1 d . . . . .
C11 C 0.0597(3) 0.6900(3) 0.3792(2) 0.0349(6) Uani 1 1 d . . . . .
H11A H -0.0210 0.7790 0.3756 0.052 Uiso 1 1 calc GR . . . .
H11B H 0.0257 0.6283 0.4209 0.052 Uiso 1 1 calc GR . . . .
H11C H 0.1134 0.6514 0.3014 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.2423(3) 0.4800(3) 0.5370(2) 0.0342(6) Uani 1 1 d . . . . .
H12A H 0.3422 0.4140 0.5330 0.041 Uiso 1 1 calc R . . . .
H12B H 0.2130 0.4500 0.4782 0.041 Uiso 1 1 calc R . . . .
C13 C 0.1528(3) 0.4762(3) 0.6540(2) 0.0406(6) Uani 1 1 d . . . . .
H13A H 0.0530 0.5382 0.6579 0.061 Uiso 1 1 calc GR . . . .
H13B H 0.1816 0.5048 0.7131 0.061 Uiso 1 1 calc GR . . . .
H13C H 0.1661 0.3831 0.6666 0.061 Uiso 1 1 calc GR . . . .
C14 C 0.3908(3) 0.6409(3) 0.6261(2) 0.0313(5) Uani 1 1 d . . . . .
H14 H 0.4175 0.7053 0.6438 0.038 Uiso 1 1 calc R . . . .
C15 C 0.4402(3) 0.5216(3) 0.6778(2) 0.0311(5) Uani 1 1 d . . . . .
H15 H 0.4167 0.4552 0.6588 0.037 Uiso 1 1 calc R . . . .
C16 C 0.5259(2) 0.4849(3) 0.7595(2) 0.0295(5) Uani 1 1 d . . . . .
C17 C 0.5647(2) 0.5736(3) 0.8003(2) 0.0311(5) Uani 1 1 d . . . . .
H17 H 0.5331 0.6632 0.7733 0.037 Uiso 1 1 calc R . . . .
C18 C 0.6474(2) 0.5350(3) 0.8783(2) 0.0306(5) Uani 1 1 d . . . . .
C19 C 0.6985(2) 0.3999(3) 0.9165(2) 0.0296(5) Uani 1 1 d . . . . .
C20 C 0.6566(2) 0.3112(3) 0.8790(2) 0.0303(5) Uani 1 1 d . . . . .
C21 C 0.5732(3) 0.3550(3) 0.8025(2) 0.0313(5) Uani 1 1 d . . . . .
H21 H 0.5466 0.2938 0.7778 0.038 Uiso 1 1 calc R . . . .
C22 C 0.6828(3) 0.6331(3) 0.9235(2) 0.0391(6) Uani 1 1 d . . . . .
H22A H 0.6090 0.6833 0.9930 0.047 Uiso 1 1 calc R . . . .
H22B H 0.6848 0.7004 0.8654 0.047 Uiso 1 1 calc R . . . .
C23 C 0.8256(3) 0.5578(3) 0.9522(3) 0.0452(7) Uani 1 1 d . . . . .
H23A H 0.9013 0.5158 0.8815 0.054 Uiso 1 1 calc R . . . .
H23B H 0.8444 0.6226 0.9877 0.054 Uiso 1 1 calc R . . . .
C24 C 0.8240(3) 0.4484(3) 1.0342(2) 0.0429(7) Uani 1 1 d . . . . .
H24A H 0.9174 0.3972 1.0520 0.052 Uiso 1 1 calc R . . . .
H24B H 0.7523 0.4918 1.1066 0.052 Uiso 1 1 calc R . . . .
C25 C 0.7024(3) 0.1692(3) 0.9239(2) 0.0382(6) Uani 1 1 d . . . . .
H25A H 0.6273 0.1708 0.9899 0.046 Uiso 1 1 calc R . . . .
H25B H 0.7160 0.1056 0.8635 0.046 Uiso 1 1 calc R . . . .
C26 C 0.8387(3) 0.1185(3) 0.9607(3) 0.0422(7) Uani 1 1 d . . . . .
H26A H 0.8590 0.0322 1.0000 0.051 Uiso 1 1 calc R . . . .
H26B H 0.9179 0.1003 0.8926 0.051 Uiso 1 1 calc R . . . .
C27 C 0.8252(3) 0.2248(3) 1.0403(2) 0.0431(7) Uani 1 1 d . . . . .
H27A H 0.7498 0.2384 1.1104 0.052 Uiso 1 1 calc R . . . .
H27B H 0.9150 0.1922 1.0630 0.052 Uiso 1 1 calc R . . . .
C28 C 0.3432(4) 0.1064(5) 0.7795(3) 0.0744(12) Uani 1 1 d . . . . .
H28A H 0.3669 0.0265 0.7313 0.089 Uiso 1 1 calc R . . . .
H28B H 0.3642 0.1717 0.7284 0.089 Uiso 1 1 calc R . . . .
B4 B 0.3278(4) 0.9049(3) 0.5073(3) 0.0382(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
Cl1 C28 1.758(4) . ?
Cl2 C28 1.721(4) . ?
F1 B4 1.378(4) . ?
F2 B4 1.393(4) . ?
N1 C5 1.359(3) . ?
N1 C10 1.381(3) . ?
N1 B4 1.533(4) . ?
N2 C3 1.360(3) . ?
N2 C9 1.393(3) . ?
N2 B4 1.553(3) . ?
N3 C19 1.379(3) . ?
N3 C24 1.459(4) . ?
N3 C27 1.457(4) . ?
C1 C2 1.375(3) . ?
C1 C9 1.439(3) . ?
C1 C11 1.489(3) . ?
C2 C3 1.442(3) . ?
C2 C12 1.506(3) . ?
C3 C14 1.436(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(4) . ?
C7 H7 0.9500 . ?
C7 C10 1.399(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.366(3) . ?
C8 C10 1.406(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.518(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.347(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.448(3) . ?
C16 C17 1.407(4) . ?
C16 C21 1.394(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(4) . ?
C18 C19 1.420(4) . ?
C18 C22 1.498(4) . ?
C19 C20 1.414(4) . ?
C20 C21 1.375(3) . ?
C20 C25 1.517(4) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.521(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.515(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.515(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.511(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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 N1 C10 107.8(2) . . ?
C5 N1 B4 126.5(2) . . ?
C10 N1 B4 125.7(2) . . ?
C3 N2 C9 108.44(19) . . ?
C3 N2 B4 127.8(2) . . ?
C9 N2 B4 123.68(19) . . ?
C19 N3 C24 120.7(2) . . ?
C19 N3 C27 120.4(2) . . ?
C27 N3 C24 116.1(2) . . ?
C2 C1 C9 107.4(2) . . ?
C2 C1 C11 128.3(2) . . ?
C9 C1 C11 124.2(2) . . ?
C1 C2 C3 107.2(2) . . ?
C1 C2 C12 125.2(2) . . ?
C3 C2 C12 127.6(2) . . ?
N2 C3 C2 108.9(2) . . ?
N2 C3 C14 119.3(2) . . ?
C14 C3 C2 131.8(2) . . ?
N1 C5 H5 125.2 . . ?
N1 C5 C6 109.6(3) . . ?
C6 C5 H5 125.2 . . ?
C5 C6 H6 126.3 . . ?
C5 C6 C7 107.3(2) . . ?
C7 C6 H6 126.3 . . ?
C6 C7 H7 126.4 . . ?
C6 C7 C10 107.1(2) . . ?
C10 C7 H7 126.4 . . ?
C9 C8 H8 119.1 . . ?
C9 C8 C10 121.8(2) . . ?
C10 C8 H8 119.1 . . ?
N2 C9 C1 107.96(19) . . ?
C8 C9 N2 121.5(2) . . ?
C8 C9 C1 130.5(2) . . ?
N1 C10 C7 108.2(2) . . ?
N1 C10 C8 119.6(2) . . ?
C7 C10 C8 132.3(2) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 108.7 . . ?
C2 C12 H12B 108.7 . . ?
C2 C12 C13 114.1(2) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 H14 116.2 . . ?
C15 C14 C3 127.7(2) . . ?
C15 C14 H14 116.2 . . ?
C14 C15 H15 116.9 . . ?
C14 C15 C16 126.2(2) . . ?
C16 C15 H15 116.9 . . ?
C17 C16 C15 123.9(2) . . ?
C21 C16 C15 119.3(2) . . ?
C21 C16 C17 116.8(2) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 C16 122.5(2) . . ?
C18 C17 H17 118.8 . . ?
C17 C18 C19 119.1(2) . . ?
C17 C18 C22 121.3(2) . . ?
C19 C18 C22 119.6(2) . . ?
N3 C19 C18 120.6(2) . . ?
N3 C19 C20 120.4(2) . . ?
C20 C19 C18 118.9(2) . . ?
C19 C20 C25 120.0(2) . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 C25 120.3(2) . . ?
C16 C21 H21 118.5 . . ?
C20 C21 C16 123.0(2) . . ?
C20 C21 H21 118.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 C23 110.6(2) . . ?
H22A C22 H22B 108.1 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C22 C23 H23A 109.9 . . ?
C22 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C24 C23 C22 108.7(2) . . ?
C24 C23 H23A 109.9 . . ?
C24 C23 H23B 109.9 . . ?
N3 C24 C23 111.1(2) . . ?
N3 C24 H24A 109.4 . . ?
N3 C24 H24B 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C20 C25 H25A 109.4 . . ?
C20 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C26 C25 C20 111.2(2) . . ?
C26 C25 H25A 109.4 . . ?
C26 C25 H25B 109.4 . . ?
C25 C26 H26A 109.7 . . ?
C25 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 C25 109.6(2) . . ?
C27 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
N3 C27 C26 110.9(2) . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 108.0 . . ?
Cl1 C28 H28A 108.7 . . ?
Cl1 C28 H28B 108.7 . . ?
Cl2 C28 Cl1 114.2(2) . . ?
Cl2 C28 H28A 108.7 . . ?
Cl2 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
F1 B4 F2 109.2(2) . . ?
F1 B4 N1 110.2(2) . . ?
F1 B4 N2 110.3(2) . . ?
F2 B4 N1 109.8(2) . . ?
F2 B4 N2 109.6(2) . . ?
N1 B4 N2 107.7(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
N1 C5 C6 C7 -0.2(3) . . . . ?
N2 C3 C14 C15 -176.5(2) . . . . ?
N3 C19 C20 C21 -174.4(2) . . . . ?
N3 C19 C20 C25 6.2(3) . . . . ?
C1 C2 C3 N2 -1.7(3) . . . . ?
C1 C2 C3 C14 175.7(3) . . . . ?
C1 C2 C12 C13 -101.6(3) . . . . ?
C2 C1 C9 N2 -0.4(3) . . . . ?
C2 C1 C9 C8 178.4(3) . . . . ?
C2 C3 C14 C15 6.3(5) . . . . ?
C3 N2 C9 C1 -0.7(3) . . . . ?
C3 N2 C9 C8 -179.6(2) . . . . ?
C3 N2 B4 F1 -62.9(3) . . . . ?
C3 N2 B4 F2 57.4(3) . . . . ?
C3 N2 B4 N1 176.8(2) . . . . ?
C3 C2 C12 C13 79.3(3) . . . . ?
C3 C14 C15 C16 -178.0(2) . . . . ?
C5 N1 C10 C7 0.0(3) . . . . ?
C5 N1 C10 C8 179.7(2) . . . . ?
C5 N1 B4 F1 59.5(4) . . . . ?
C5 N1 B4 F2 -60.9(4) . . . . ?
C5 N1 B4 N2 179.9(2) . . . . ?
C5 C6 C7 C10 0.2(3) . . . . ?
C6 C7 C10 N1 -0.1(3) . . . . ?
C6 C7 C10 C8 -179.8(3) . . . . ?
C9 N2 C3 C2 1.5(3) . . . . ?
C9 N2 C3 C14 -176.3(2) . . . . ?
C9 N2 B4 F1 121.0(3) . . . . ?
C9 N2 B4 F2 -118.7(3) . . . . ?
C9 N2 B4 N1 0.7(3) . . . . ?
C9 C1 C2 C3 1.3(3) . . . . ?
C9 C1 C2 C12 -178.0(2) . . . . ?
C9 C8 C10 N1 -0.6(4) . . . . ?
C9 C8 C10 C7 179.1(3) . . . . ?
C10 N1 C5 C6 0.2(3) . . . . ?
C10 N1 B4 F1 -118.8(3) . . . . ?
C10 N1 B4 F2 120.8(3) . . . . ?
C10 N1 B4 N2 1.6(4) . . . . ?
C10 C8 C9 N2 2.8(4) . . . . ?
C10 C8 C9 C1 -175.9(2) . . . . ?
C11 C1 C2 C3 -179.5(2) . . . . ?
C11 C1 C2 C12 1.2(4) . . . . ?
C11 C1 C9 N2 -179.7(2) . . . . ?
C11 C1 C9 C8 -0.8(4) . . . . ?
C12 C2 C3 N2 177.5(2) . . . . ?
C12 C2 C3 C14 -5.1(4) . . . . ?
C14 C15 C16 C17 2.8(4) . . . . ?
C14 C15 C16 C21 -177.7(2) . . . . ?
C15 C16 C17 C18 -179.8(2) . . . . ?
C15 C16 C21 C20 179.0(2) . . . . ?
C16 C17 C18 C19 1.8(4) . . . . ?
C16 C17 C18 C22 -177.8(2) . . . . ?
C17 C16 C21 C20 -1.5(4) . . . . ?
C17 C18 C19 N3 173.8(2) . . . . ?
C17 C18 C19 C20 -3.7(3) . . . . ?
C17 C18 C22 C23 -149.9(2) . . . . ?
C18 C19 C20 C21 3.0(3) . . . . ?
C18 C19 C20 C25 -176.4(2) . . . . ?
C18 C22 C23 C24 -55.0(3) . . . . ?
C19 N3 C24 C23 -35.3(3) . . . . ?
C19 N3 C27 C26 39.5(3) . . . . ?
C19 C18 C22 C23 30.5(3) . . . . ?
C19 C20 C21 C16 -0.4(4) . . . . ?
C19 C20 C25 C26 -26.2(3) . . . . ?
C20 C25 C26 C27 51.1(3) . . . . ?
C21 C16 C17 C18 0.8(3) . . . . ?
C21 C20 C25 C26 154.5(2) . . . . ?
C22 C18 C19 N3 -6.7(3) . . . . ?
C22 C18 C19 C20 175.9(2) . . . . ?
C22 C23 C24 N3 57.7(3) . . . . ?
C24 N3 C19 C18 9.0(3) . . . . ?
C24 N3 C19 C20 -173.6(2) . . . . ?
C24 N3 C27 C26 -159.2(2) . . . . ?
C25 C20 C21 C16 179.0(2) . . . . ?
C25 C26 C27 N3 -58.0(3) . . . . ?
C27 N3 C19 C18 169.5(2) . . . . ?
C27 N3 C19 C20 -13.1(4) . . . . ?
C27 N3 C24 C23 163.5(2) . . . . ?
B4 N1 C5 C6 -178.4(3) . . . . ?
B4 N1 C10 C7 178.5(3) . . . . ?
B4 N1 C10 C8 -1.7(4) . . . . ?
B4 N2 C3 C2 -175.1(2) . . . . ?
B4 N2 C3 C14 7.1(4) . . . . ?
B4 N2 C9 C1 176.1(2) . . . . ?
B4 N2 C9 C8 -2.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.798
