# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# 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_d1801a_a
_database_code_depnum_ccdc_archive 'CCDC 2051782'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        Cl-aF3BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H9 B Cl F3 N6'
_chemical_formula_sum            'C24 H9 B Cl F3 N6'
_chemical_formula_weight         484.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.3458(6)
_cell_length_b                   15.1437(7)
_cell_length_c                   10.3431(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1933.76(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      5.18
_cell_measurement_theta_max      66.54

_exptl_crystal_description       Block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.271
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6666
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26520
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.178
_diffrn_reflns_theta_max         67.263
_diffrn_reflns_theta_full        67.263
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1795
_reflns_number_gt                1604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+1.3142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1795
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.82433(5) 0.750000 0.74084(6) 0.03404(18) Uani 1 2 d S T P . .
C3 C 1.04167(15) 0.54401(14) 0.31742(17) 0.0366(4) Uani 0.736(3) 1 d . . P A 1
F1 F 1.13243(11) 0.58395(10) 0.30094(14) 0.0394(5) Uani 0.736(3) 1 d . . P A 1
C3A C 1.04167(15) 0.54401(14) 0.31742(17) 0.0366(4) Uani 0.264(3) 1 d . . P A 2
H3A H 1.107195 0.575023 0.301354 0.044 Uiso 0.264(3) 1 calc R U P A 2
C6 C 0.84926(18) 0.45214(13) 0.35977(17) 0.0393(5) Uani 0.736(3) 1 d . . P A 1
H6 H 0.783437 0.420882 0.372804 0.047 Uiso 0.736(3) 1 calc R U P A 1
C6A C 0.84926(18) 0.45214(13) 0.35977(17) 0.0393(5) Uani 0.264(3) 1 d . . P A 2
F2 F 0.7745(3) 0.4101(3) 0.3810(4) 0.0416(14) Uani 0.264(3) 1 d . . P A 2
C11 C 0.42551(17) 0.6571(2) 0.43979(19) 0.0537(7) Uani 0.5 1 d . . P B 1
C11A C 0.42551(17) 0.6571(2) 0.43979(19) 0.0537(7) Uani 0.5 1 d . . P B 2
H11A H 0.424991 0.594388 0.439299 0.064 Uiso 0.5 1 calc R U P B 2
F3 F 0.41664(17) 0.58231(16) 0.4397(2) 0.0424(5) Uani 0.5 1 d . . P B 1
N1 N 0.99797(16) 0.750000 0.41067(19) 0.0289(5) Uani 1 2 d S T P . .
N2 N 0.84628(11) 0.67253(10) 0.49548(13) 0.0275(3) Uani 1 1 d . . . . .
N3 N 0.67814(12) 0.59680(11) 0.47835(14) 0.0334(4) Uani 1 1 d . . . . .
N4 N 0.68396(16) 0.750000 0.52861(19) 0.0291(5) Uani 1 2 d S T P . .
C1 C 0.94469(13) 0.67429(12) 0.43470(15) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.95888(15) 0.58568(12) 0.38317(16) 0.0304(4) Uani 1 1 d . . . . .
C4 C 1.03106(18) 0.45848(14) 0.27475(17) 0.0419(5) Uani 1 1 d . . . . .
H4 H 1.089181 0.430624 0.230471 0.050 Uiso 1 1 calc R U . A 1
C5 C 0.93488(18) 0.41274(14) 0.29660(18) 0.0423(5) Uani 1 1 d . . . . .
H5 H 0.928199 0.353486 0.267517 0.051 Uiso 1 1 calc R U . A 1
C7 C 0.86068(15) 0.53821(12) 0.40408(16) 0.0313(4) Uani 1 1 d . . . . .
C8 C 0.78653(15) 0.59843(12) 0.46877(16) 0.0297(4) Uani 1 1 d . . . . .
C9 C 0.62879(15) 0.67390(13) 0.49992(16) 0.0330(4) Uani 1 1 d . . . . .
C10 C 0.51874(15) 0.70301(15) 0.47129(16) 0.0382(5) Uani 1 1 d . . . . .
C12 C 0.33317(16) 0.7042(2) 0.4090(2) 0.0654(8) Uani 1 1 d . . . . .
H12 H 0.268640 0.673312 0.387561 0.078 Uiso 1 1 calc R U . B 1
B1 B 0.8004(2) 0.750000 0.5618(3) 0.0283(6) Uani 1 2 d S T P . .


_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 B1 1.875(3) . ?
C3 F1 1.285(2) . ?
C3 C4 1.375(3) . ?
C3 C2 1.380(3) . ?
C3A C4 1.375(3) . ?
C3A C2 1.380(3) . ?
C3A H3A 0.9500 . ?
C6 C5 1.379(3) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C6A F2 1.142(5) . ?
C6A C5 1.379(3) . ?
C6A C7 1.389(3) . ?
C11 F3 1.138(3) . ?
C11 C12 1.381(4) . ?
C11 C10 1.384(3) . ?
C11A C12 1.381(4) . ?
C11A C10 1.384(3) . ?
C11A H11A 0.9500 . ?
N1 C1 1.345(2) . ?
N1 C1 1.345(2) 7_575 ?
N2 C1 1.368(2) . ?
N2 C8 1.371(2) . ?
N2 B1 1.472(2) . ?
N3 C9 1.336(2) . ?
N3 C8 1.342(2) . ?
N4 C9 1.371(2) 7_575 ?
N4 C9 1.371(2) . ?
N4 B1 1.478(3) . ?
C1 C2 1.454(3) . ?
C2 C7 1.426(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.455(3) . ?
C9 C10 1.459(3) . ?
C10 C10 1.423(4) 7_575 ?
C12 C12 1.388(6) 7_575 ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C3 C4 118.96(18) . . ?
F1 C3 C2 119.74(18) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3A C2 121.2(2) . . ?
C4 C3A H3A 119.4 . . ?
C2 C3A H3A 119.4 . . ?
C5 C6 C7 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
F2 C6A C5 118.0(3) . . ?
F2 C6A C7 122.8(3) . . ?
C5 C6A C7 119.0(2) . . ?
F3 C11 C12 115.7(2) . . ?
F3 C11 C10 125.5(3) . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11A C10 118.8(3) . . ?
C12 C11A H11A 120.6 . . ?
C10 C11A H11A 120.6 . . ?
C1 N1 C1 117.0(2) . 7_575 ?
C1 N2 C8 113.64(15) . . ?
C1 N2 B1 122.72(16) . . ?
C8 N2 B1 122.60(16) . . ?
C9 N3 C8 116.81(16) . . ?
C9 N4 C9 114.4(2) 7_575 . ?
C9 N4 B1 122.23(11) 7_575 . ?
C9 N4 B1 122.24(11) . . ?
N1 C1 N2 122.39(16) . . ?
N1 C1 C2 131.29(16) . . ?
N2 C1 C2 104.92(15) . . ?
C3A C2 C7 118.29(17) . . ?
C3 C2 C7 118.29(17) . . ?
C3A C2 C1 133.74(18) . . ?
C3 C2 C1 133.74(18) . . ?
C7 C2 C1 107.88(15) . . ?
C3A C4 C5 119.84(19) . . ?
C3 C4 C5 119.84(19) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6A C5 C4 121.02(19) . . ?
C6 C5 C4 121.02(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C6A C7 C2 120.62(18) . . ?
C6 C7 C2 120.62(18) . . ?
C6A C7 C8 132.54(18) . . ?
C6 C7 C8 132.54(18) . . ?
C2 C7 C8 106.78(15) . . ?
N3 C8 N2 122.46(17) . . ?
N3 C8 C7 130.51(17) . . ?
N2 C8 C7 105.50(15) . . ?
N3 C9 N4 122.97(16) . . ?
N3 C9 C10 130.93(17) . . ?
N4 C9 C10 104.63(17) . . ?
C11 C10 C10 120.15(16) . 7_575 ?
C11A C10 C9 132.1(2) . . ?
C11 C10 C9 132.1(2) . . ?
C10 C10 C9 107.59(11) 7_575 . ?
C11A C12 C12 121.05(17) . 7_575 ?
C11 C12 C12 121.05(17) . 7_575 ?
C11 C12 H12 119.5 . . ?
C12 C12 H12 119.5 7_575 . ?
N2 B1 N2 105.6(2) 7_575 . ?
N2 B1 N4 105.45(15) 7_575 . ?
N2 B1 N4 105.45(15) . . ?
N2 B1 Cl1 113.53(13) 7_575 . ?
N2 B1 Cl1 113.53(13) . . ?
N4 B1 Cl1 112.51(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C1 N2 -7.9(3) 7_575 . . . ?
C1 N1 C1 C2 156.45(13) 7_575 . . . ?
C8 N2 C1 N1 156.38(17) . . . . ?
B1 N2 C1 N1 -12.2(3) . . . . ?
C8 N2 C1 C2 -11.50(18) . . . . ?
B1 N2 C1 C2 179.89(17) . . . . ?
C4 C3A C2 C7 -1.1(3) . . . . ?
C4 C3A C2 C1 -177.29(18) . . . . ?
F1 C3 C2 C7 -177.63(16) . . . . ?
C4 C3 C2 C7 -1.1(3) . . . . ?
F1 C3 C2 C1 6.2(3) . . . . ?
C4 C3 C2 C1 -177.29(18) . . . . ?
N1 C1 C2 C3A 16.8(3) . . . . ?
N2 C1 C2 C3A -176.89(18) . . . . ?
N1 C1 C2 C3 16.8(3) . . . . ?
N2 C1 C2 C3 -176.89(18) . . . . ?
N1 C1 C2 C7 -159.75(19) . . . . ?
N2 C1 C2 C7 6.60(17) . . . . ?
C2 C3A C4 C5 0.7(3) . . . . ?
F1 C3 C4 C5 177.27(17) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
F2 C6A C5 C4 -176.0(3) . . . . ?
C7 C6A C5 C4 -1.2(3) . . . . ?
C7 C6 C5 C4 -1.2(3) . . . . ?
C3A C4 C5 C6A 0.5(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
F2 C6A C7 C2 175.3(3) . . . . ?
C5 C6A C7 C2 0.8(3) . . . . ?
F2 C6A C7 C8 -8.0(4) . . . . ?
C5 C6A C7 C8 177.55(18) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C5 C6 C7 C8 177.55(18) . . . . ?
C3A C2 C7 C6A 0.3(2) . . . . ?
C1 C2 C7 C6A 177.44(15) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C1 C2 C7 C6 177.44(15) . . . . ?
C3A C2 C7 C8 -177.17(15) . . . . ?
C3 C2 C7 C8 -177.17(15) . . . . ?
C1 C2 C7 C8 -0.04(18) . . . . ?
C9 N3 C8 N2 8.0(2) . . . . ?
C9 N3 C8 C7 -155.73(18) . . . . ?
C1 N2 C8 N3 -155.70(16) . . . . ?
B1 N2 C8 N3 12.9(3) . . . . ?
C1 N2 C8 C7 11.55(19) . . . . ?
B1 N2 C8 C7 -179.82(16) . . . . ?
C6A C7 C8 N3 -17.8(3) . . . . ?
C6 C7 C8 N3 -17.8(3) . . . . ?
C2 C7 C8 N3 159.27(18) . . . . ?
C6A C7 C8 N2 176.39(18) . . . . ?
C6 C7 C8 N2 176.39(18) . . . . ?
C2 C7 C8 N2 -6.55(18) . . . . ?
C8 N3 C9 N4 -8.6(3) . . . . ?
C8 N3 C9 C10 155.30(18) . . . . ?
C9 N4 C9 N3 156.44(12) 7_575 . . . ?
B1 N4 C9 N3 -11.6(3) . . . . ?
C9 N4 C9 C10 -11.1(3) 7_575 . . . ?
B1 N4 C9 C10 -179.10(19) . . . . ?
C12 C11A C10 C10 -0.2(2) . . . 7_575 ?
C12 C11A C10 C9 -175.70(18) . . . . ?
F3 C11 C10 C10 -178.2(2) . . . 7_575 ?
C12 C11 C10 C10 -0.2(2) . . . 7_575 ?
F3 C11 C10 C9 6.3(4) . . . . ?
C12 C11 C10 C9 -175.70(18) . . . . ?
N3 C9 C10 C11A 16.1(3) . . . . ?
N4 C9 C10 C11A -177.83(19) . . . . ?
N3 C9 C10 C11 16.1(3) . . . . ?
N4 C9 C10 C11 -177.83(19) . . . . ?
N3 C9 C10 C10 -159.85(16) . . . 7_575 ?
N4 C9 C10 C10 6.27(14) . . . 7_575 ?
C10 C11A C12 C12 0.2(2) . . . 7_575 ?
F3 C11 C12 C12 178.42(17) . . . 7_575 ?
C10 C11 C12 C12 0.2(2) . . . 7_575 ?
C1 N2 B1 N2 27.7(3) . . . 7_575 ?
C8 N2 B1 N2 -139.86(15) . . . 7_575 ?
C1 N2 B1 N4 139.11(16) . . . . ?
C8 N2 B1 N4 -28.5(2) . . . . ?
C1 N2 B1 Cl1 -97.29(18) . . . . ?
C8 N2 B1 Cl1 95.1(2) . . . . ?
C9 N4 B1 N2 -27.8(3) 7_575 . . 7_575 ?
C9 N4 B1 N2 139.29(17) . . . 7_575 ?
C9 N4 B1 N2 -139.29(17) 7_575 . . . ?
C9 N4 B1 N2 27.8(3) . . . . ?
C9 N4 B1 Cl1 96.46(18) 7_575 . . . ?
C9 N4 B1 Cl1 -96.46(18) . . . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045



_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_d1930_a
_database_code_depnum_ccdc_archive 'CCDC 2051785'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        Cl-bCl3BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H9.11 B Cl3.89 N6'
_chemical_formula_sum            'C24 H9.11 B Cl3.89 N6'
_chemical_formula_weight         530.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1595(6)
_cell_length_b                   10.3924(4)
_cell_length_c                   19.5637(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.519(4)
_cell_angle_gamma                90
_cell_volume                     2214.94(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3197
_cell_measurement_theta_min      4.06
_cell_measurement_theta_max      66.95

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             1065
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    4.969
_shelx_estimated_absorpt_T_min   0.636
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6155
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30857
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.058
_diffrn_reflns_theta_max         67.985
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4019
_reflns_number_gt                2792
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       APEX3
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+5.1017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4019
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.2072
_refine_ls_wR_factor_gt          0.1858
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.47256(13) 0.92529(11) 0.29270(7) 0.0619(4) Uani 1 1 d . . . . .
Cl2 Cl 0.9914(6) 0.3225(6) 0.4667(4) 0.103(3) Uani 0.295(7) 1 d . . P A 1
Cl3 Cl 0.8256(2) 0.2970(2) 0.55316(12) 0.0857(10) Uani 0.694(6) 1 d . . P A 1
Cl4 Cl -0.0536(2) 0.3173(2) 0.26613(15) 0.0743(11) Uani 0.566(6) 1 d . . P B 1
Cl5 Cl -0.1182(5) 0.3775(5) 0.1584(4) 0.128(3) Uani 0.412(7) 1 d . . P B 1
Cl6 Cl 0.8451(3) 0.6319(3) -0.01836(12) 0.1398(15) Uani 0.923(8) 1 d . . P C 1
N1 N 0.5775(4) 0.6812(3) 0.32148(19) 0.0469(9) Uani 1 1 d . . . . .
N2 N 0.4239(4) 0.5733(4) 0.3665(2) 0.0547(10) Uani 1 1 d . . . . .
N3 N 0.3741(4) 0.6812(4) 0.2572(2) 0.0545(10) Uani 1 1 d . . . . .
N4 N 0.3397(5) 0.6853(4) 0.1327(3) 0.0706(13) Uani 1 1 d . . . . .
N5 N 0.5335(4) 0.7398(4) 0.2022(2) 0.0566(11) Uani 1 1 d . . . . .
N6 N 0.7373(4) 0.6822(4) 0.2584(2) 0.0556(10) Uani 1 1 d . . . . .
C1 C 0.6958(5) 0.6564(4) 0.3160(3) 0.0509(11) Uani 1 1 d . . . . .
C2 C 0.7465(5) 0.5733(5) 0.3741(3) 0.0545(12) Uani 1 1 d . . . . .
C3 C 0.8615(5) 0.5145(6) 0.3928(3) 0.0668(15) Uani 1 1 d . . . . .
H3A H 0.925101 0.533960 0.369112 0.080 Uiso 1 1 calc R U . A 1
C4 C 0.8791(6) 0.4271(6) 0.4470(3) 0.0763(17) Uani 0.295(7) 1 d . . P A 1
C5 C 0.7884(6) 0.4018(5) 0.4836(3) 0.0693(16) Uani 0.694(6) 1 d . . P A 1
C4A C 0.8791(6) 0.4271(6) 0.4470(3) 0.0763(17) Uani 0.705(7) 1 d . . P A 2
H4A H 0.955303 0.383006 0.459636 0.092 Uiso 0.705(7) 1 calc R U P A 2
C5A C 0.7884(6) 0.4018(5) 0.4836(3) 0.0693(16) Uani 0.306(6) 1 d . . P A 2
H5A H 0.805266 0.343877 0.522052 0.083 Uiso 0.306(6) 1 calc R U P A 2
C6 C 0.6741(5) 0.4589(5) 0.4655(3) 0.0606(13) Uani 1 1 d . . . . .
H6A H 0.612208 0.440751 0.490662 0.073 Uiso 1 1 calc R U . A 1
C7 C 0.6528(5) 0.5435(4) 0.4095(2) 0.0516(11) Uani 1 1 d . . . . .
C8 C 0.5416(5) 0.6043(4) 0.3704(2) 0.0495(11) Uani 1 1 d . . . . .
C9 C 0.3425(5) 0.6050(5) 0.3076(3) 0.0579(13) Uani 1 1 d . . . . .
C10 C 0.2258(5) 0.5485(5) 0.2740(4) 0.0717(17) Uani 1 1 d . . . . .
C11 C 0.1488(5) 0.4648(6) 0.3002(5) 0.088(2) Uani 1 1 d . . . . .
H11 H 0.163646 0.438904 0.347886 0.106 Uiso 1 1 calc R U . B 1
C12 C 0.0461(7) 0.4217(7) 0.2490(7) 0.116(4) Uani 0.566(6) 1 d . . P B 1
C13 C 0.0221(8) 0.4580(9) 0.1783(7) 0.122(4) Uani 0.412(7) 1 d . . P B 1
C12A C 0.0461(7) 0.4217(7) 0.2490(7) 0.116(4) Uani 0.434(6) 1 d . . P B 2
H12A H -0.009962 0.364697 0.263674 0.140 Uiso 0.434(6) 1 calc R U P B 2
C13A C 0.0221(8) 0.4580(9) 0.1783(7) 0.122(4) Uani 0.588(7) 1 d . . P B 2
H13A H -0.048399 0.425949 0.146588 0.147 Uiso 0.588(7) 1 calc R U P B 2
C14 C 0.0981(6) 0.5369(7) 0.1560(5) 0.101(3) Uani 1 1 d . . . . .
H14 H 0.082536 0.561793 0.108157 0.121 Uiso 1 1 calc R U . B 1
C15 C 0.2002(5) 0.5832(6) 0.2024(4) 0.0785(19) Uani 1 1 d . . . . .
C16 C 0.3021(5) 0.6611(5) 0.1918(3) 0.0644(14) Uani 1 1 d . . . . .
C17 C 0.4577(6) 0.7151(5) 0.1388(3) 0.0642(15) Uani 1 1 d . . . . .
C18 C 0.5360(7) 0.6986(5) 0.0900(3) 0.0704(17) Uani 1 1 d . . . . .
C19 C 0.5102(8) 0.6712(5) 0.0174(3) 0.085(2) Uani 1 1 d . . . . .
H19A H 0.428103 0.667657 -0.009006 0.102 Uiso 1 1 calc R U . . .
C20 C 0.6086(10) 0.6497(6) -0.0139(4) 0.096(3) Uani 1 1 d . . . . .
H20A H 0.594192 0.632115 -0.062616 0.115 Uiso 1 1 calc R U . C 1
C21 C 0.7281(10) 0.6538(6) 0.0255(4) 0.096(3) Uani 0.923(8) 1 d . . P C 1
C21A C 0.7281(10) 0.6538(6) 0.0255(4) 0.096(3) Uani 0.077(8) 1 d . . P C 2
H21A H 0.793429 0.639824 0.002225 0.115 Uiso 0.077(8) 1 calc R U P C 2
C22 C 0.7568(7) 0.6771(5) 0.0965(3) 0.0787(18) Uani 1 1 d . . . . .
H22A H 0.839243 0.677112 0.122525 0.094 Uiso 1 1 calc R U . C 1
C23 C 0.6575(6) 0.7006(5) 0.1282(3) 0.0654(15) Uani 1 1 d . . . . .
C24 C 0.6543(6) 0.7156(5) 0.2015(3) 0.0590(13) Uani 1 1 d . . . . .
B1 B 0.4896(5) 0.7528(5) 0.2675(3) 0.0508(13) 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 B1 1.879(5) . ?
Cl2 C4 1.640(8) . ?
Cl3 C5 1.722(6) . ?
Cl4 C12 1.639(8) . ?
Cl4 Cl5 2.167(7) . ?
Cl5 C13 1.744(10) . ?
Cl6 C21 1.725(8) . ?
N1 C1 1.371(6) . ?
N1 C8 1.372(6) . ?
N1 B1 1.477(7) . ?
N2 C8 1.339(6) . ?
N2 C9 1.345(7) . ?
N3 C9 1.369(7) . ?
N3 C16 1.372(7) . ?
N3 B1 1.464(7) . ?
N4 C17 1.332(8) . ?
N4 C16 1.337(8) . ?
N5 C17 1.365(7) . ?
N5 C24 1.374(7) . ?
N5 B1 1.471(7) . ?
N6 C24 1.331(7) . ?
N6 C1 1.335(6) . ?
C1 C2 1.442(7) . ?
C2 C3 1.397(7) . ?
C2 C7 1.408(7) . ?
C3 C4A 1.378(9) . ?
C3 C4 1.378(9) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(9) . ?
C5 C6 1.382(8) . ?
C4A C5A 1.385(9) . ?
C4A H4A 0.9500 . ?
C5A C6 1.382(8) . ?
C5A H5A 0.9500 . ?
C6 C7 1.385(7) . ?
C6 H6A 0.9500 . ?
C7 C8 1.453(7) . ?
C9 C10 1.449(8) . ?
C10 C11 1.396(9) . ?
C10 C15 1.416(10) . ?
C11 C12A 1.420(12) . ?
C11 C12 1.420(12) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(15) . ?
C13 C14 1.320(14) . ?
C12A C13A 1.404(15) . ?
C12A H12A 0.9500 . ?
C13A C14 1.320(14) . ?
C13A H13A 0.9500 . ?
C14 C15 1.380(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.446(9) . ?
C17 C18 1.439(8) . ?
C18 C23 1.400(9) . ?
C18 C19 1.414(8) . ?
C19 C20 1.387(11) . ?
C19 H19A 0.9500 . ?
C20 C21A 1.388(12) . ?
C20 C21 1.388(12) . ?
C20 H20A 0.9500 . ?
C21 C22 1.377(9) . ?
C21A C22 1.377(9) . ?
C21A H21A 0.9500 . ?
C22 C23 1.404(9) . ?
C22 H22A 0.9500 . ?
C23 C24 1.452(7) . ?

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
C12 Cl4 Cl5 73.1(5) . . ?
C13 Cl5 Cl4 80.1(5) . . ?
C1 N1 C8 112.1(4) . . ?
C1 N1 B1 122.7(4) . . ?
C8 N1 B1 122.9(4) . . ?
C8 N2 C9 117.5(4) . . ?
C9 N3 C16 113.1(5) . . ?
C9 N3 B1 123.5(4) . . ?
C16 N3 B1 121.8(5) . . ?
C17 N4 C16 117.1(5) . . ?
C17 N5 C24 112.0(5) . . ?
C17 N5 B1 123.2(5) . . ?
C24 N5 B1 122.5(4) . . ?
C24 N6 C1 116.9(5) . . ?
N6 C1 N1 123.0(5) . . ?
N6 C1 C2 129.5(5) . . ?
N1 C1 C2 105.7(4) . . ?
C3 C2 C7 120.8(5) . . ?
C3 C2 C1 130.6(5) . . ?
C7 C2 C1 108.2(4) . . ?
C4A C3 C2 117.4(6) . . ?
C4 C3 C2 117.4(6) . . ?
C4 C3 H3A 121.3 . . ?
C2 C3 H3A 121.3 . . ?
C3 C4 C5 121.6(6) . . ?
C3 C4 Cl2 126.3(6) . . ?
C5 C4 Cl2 111.1(6) . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 Cl3 121.7(5) . . ?
C4 C5 Cl3 116.8(5) . . ?
C3 C4A C5A 121.6(6) . . ?
C3 C4A H4A 119.2 . . ?
C5A C4A H4A 119.2 . . ?
C6 C5A C4A 121.6(5) . . ?
C6 C5A H5A 119.2 . . ?
C4A C5A H5A 119.2 . . ?
C5A C6 C7 117.8(5) . . ?
C5 C6 C7 117.8(5) . . ?
C5 C6 H6A 121.1 . . ?
C7 C6 H6A 121.1 . . ?
C6 C7 C2 120.7(5) . . ?
C6 C7 C8 132.3(5) . . ?
C2 C7 C8 106.6(4) . . ?
N2 C8 N1 122.1(4) . . ?
N2 C8 C7 129.9(4) . . ?
N1 C8 C7 106.0(4) . . ?
N2 C9 N3 121.8(5) . . ?
N2 C9 C10 131.5(5) . . ?
N3 C9 C10 104.7(5) . . ?
C11 C10 C15 120.9(6) . . ?
C11 C10 C9 130.6(7) . . ?
C15 C10 C9 108.3(5) . . ?
C10 C11 C12A 113.8(8) . . ?
C10 C11 C12 113.8(8) . . ?
C10 C11 H11 123.1 . . ?
C12 C11 H11 123.1 . . ?
C13 C12 C11 124.3(8) . . ?
C13 C12 Cl4 112.7(8) . . ?
C11 C12 Cl4 122.9(10) . . ?
C14 C13 C12 119.6(8) . . ?
C14 C13 Cl5 146.6(10) . . ?
C12 C13 Cl5 93.5(9) . . ?
C13A C12A C11 124.3(8) . . ?
C13A C12A H12A 117.9 . . ?
C11 C12A H12A 117.9 . . ?
C14 C13A C12A 119.6(8) . . ?
C14 C13A H13A 120.2 . . ?
C12A C13A H13A 120.2 . . ?
C13A C14 C15 119.9(10) . . ?
C13 C14 C15 119.9(10) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 121.5(7) . . ?
C14 C15 C16 131.6(8) . . ?
C10 C15 C16 106.7(5) . . ?
N4 C16 N3 123.2(5) . . ?
N4 C16 C15 129.3(5) . . ?
N3 C16 C15 105.8(5) . . ?
N4 C17 N5 122.1(5) . . ?
N4 C17 C18 130.0(5) . . ?
N5 C17 C18 106.2(6) . . ?
C23 C18 C19 120.1(6) . . ?
C23 C18 C17 107.5(5) . . ?
C19 C18 C17 132.1(7) . . ?
C20 C19 C18 117.8(8) . . ?
C20 C19 H19A 121.1 . . ?
C18 C19 H19A 121.1 . . ?
C19 C20 C21A 120.5(6) . . ?
C19 C20 C21 120.5(6) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C22 C21 C20 123.3(8) . . ?
C22 C21 Cl6 119.3(8) . . ?
C20 C21 Cl6 117.4(6) . . ?
C22 C21A C20 123.3(8) . . ?
C22 C21A H21A 118.3 . . ?
C20 C21A H21A 118.3 . . ?
C21A C22 C23 116.3(8) . . ?
C21 C22 C23 116.3(8) . . ?
C21 C22 H22A 121.9 . . ?
C23 C22 H22A 121.9 . . ?
C18 C23 C22 121.9(6) . . ?
C18 C23 C24 107.5(5) . . ?
C22 C23 C24 130.3(6) . . ?
N6 C24 N5 123.1(5) . . ?
N6 C24 C23 129.6(5) . . ?
N5 C24 C23 105.3(5) . . ?
N3 B1 N5 106.4(4) . . ?
N3 B1 N1 105.7(4) . . ?
N5 B1 N1 106.3(4) . . ?
N3 B1 Cl1 112.6(4) . . ?
N5 B1 Cl1 112.8(3) . . ?
N1 B1 Cl1 112.5(4) . . ?

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
C24 N6 C1 N1 -9.9(7) . . . . ?
C24 N6 C1 C2 152.7(5) . . . . ?
C8 N1 C1 N6 155.7(4) . . . . ?
B1 N1 C1 N6 -7.6(7) . . . . ?
C8 N1 C1 C2 -10.5(5) . . . . ?
B1 N1 C1 C2 -173.7(4) . . . . ?
N6 C1 C2 C3 12.4(9) . . . . ?
N1 C1 C2 C3 177.3(5) . . . . ?
N6 C1 C2 C7 -160.5(5) . . . . ?
N1 C1 C2 C7 4.4(5) . . . . ?
C7 C2 C3 C4A -0.2(8) . . . . ?
C1 C2 C3 C4A -172.4(5) . . . . ?
C7 C2 C3 C4 -0.2(8) . . . . ?
C1 C2 C3 C4 -172.4(5) . . . . ?
C2 C3 C4 C5 -2.5(9) . . . . ?
C2 C3 C4 Cl2 164.9(5) . . . . ?
C3 C4 C5 C6 2.9(9) . . . . ?
Cl2 C4 C5 C6 -166.3(5) . . . . ?
C3 C4 C5 Cl3 -176.6(5) . . . . ?
Cl2 C4 C5 Cl3 14.3(7) . . . . ?
C2 C3 C4A C5A -2.5(9) . . . . ?
C3 C4A C5A C6 2.9(9) . . . . ?
C4A C5A C6 C7 -0.4(8) . . . . ?
C4 C5 C6 C7 -0.4(8) . . . . ?
Cl3 C5 C6 C7 179.0(4) . . . . ?
C5A C6 C7 C2 -2.3(7) . . . . ?
C5 C6 C7 C2 -2.3(7) . . . . ?
C5A C6 C7 C8 169.5(5) . . . . ?
C5 C6 C7 C8 169.5(5) . . . . ?
C3 C2 C7 C6 2.6(7) . . . . ?
C1 C2 C7 C6 176.4(4) . . . . ?
C3 C2 C7 C8 -171.1(4) . . . . ?
C1 C2 C7 C8 2.7(5) . . . . ?
C9 N2 C8 N1 9.2(6) . . . . ?
C9 N2 C8 C7 -152.2(5) . . . . ?
C1 N1 C8 N2 -153.1(4) . . . . ?
B1 N1 C8 N2 10.1(7) . . . . ?
C1 N1 C8 C7 12.2(5) . . . . ?
B1 N1 C8 C7 175.4(4) . . . . ?
C6 C7 C8 N2 -17.7(9) . . . . ?
C2 C7 C8 N2 154.9(5) . . . . ?
C6 C7 C8 N1 178.6(5) . . . . ?
C2 C7 C8 N1 -8.8(5) . . . . ?
C8 N2 C9 N3 -8.8(7) . . . . ?
C8 N2 C9 C10 152.9(5) . . . . ?
C16 N3 C9 N2 154.5(5) . . . . ?
B1 N3 C9 N2 -11.2(7) . . . . ?
C16 N3 C9 C10 -11.3(6) . . . . ?
B1 N3 C9 C10 -177.1(4) . . . . ?
N2 C9 C10 C11 17.4(10) . . . . ?
N3 C9 C10 C11 -178.7(5) . . . . ?
N2 C9 C10 C15 -157.5(5) . . . . ?
N3 C9 C10 C15 6.4(6) . . . . ?
C15 C10 C11 C12A -0.6(8) . . . . ?
C9 C10 C11 C12A -174.9(6) . . . . ?
C15 C10 C11 C12 -0.6(8) . . . . ?
C9 C10 C11 C12 -174.9(6) . . . . ?
C10 C11 C12 C13 0.2(10) . . . . ?
C10 C11 C12 Cl4 176.8(5) . . . . ?
Cl5 Cl4 C12 C13 -6.6(6) . . . . ?
Cl5 Cl4 C12 C11 176.5(7) . . . . ?
C11 C12 C13 C14 0.1(13) . . . . ?
Cl4 C12 C13 C14 -176.8(6) . . . . ?
C11 C12 C13 Cl5 -175.3(6) . . . . ?
Cl4 C12 C13 Cl5 7.8(7) . . . . ?
Cl4 Cl5 C13 C14 -178.2(13) . . . . ?
Cl4 Cl5 C13 C12 -5.5(5) . . . . ?
C10 C11 C12A C13A 0.2(10) . . . . ?
C11 C12A C13A C14 0.1(13) . . . . ?
C12A C13A C14 C15 -0.1(12) . . . . ?
C12 C13 C14 C15 -0.1(12) . . . . ?
Cl5 C13 C14 C15 171.5(10) . . . . ?
C13A C14 C15 C10 -0.3(10) . . . . ?
C13 C14 C15 C10 -0.3(10) . . . . ?
C13A C14 C15 C16 174.5(7) . . . . ?
C13 C14 C15 C16 174.5(7) . . . . ?
C11 C10 C15 C14 0.7(9) . . . . ?
C9 C10 C15 C14 176.1(5) . . . . ?
C11 C10 C15 C16 -175.2(5) . . . . ?
C9 C10 C15 C16 0.2(6) . . . . ?
C17 N4 C16 N3 8.4(7) . . . . ?
C17 N4 C16 C15 -154.3(5) . . . . ?
C9 N3 C16 N4 -154.6(5) . . . . ?
B1 N3 C16 N4 11.5(7) . . . . ?
C9 N3 C16 C15 11.6(6) . . . . ?
B1 N3 C16 C15 177.6(4) . . . . ?
C14 C15 C16 N4 -17.1(10) . . . . ?
C10 C15 C16 N4 158.3(5) . . . . ?
C14 C15 C16 N3 177.9(6) . . . . ?
C10 C15 C16 N3 -6.8(6) . . . . ?
C16 N4 C17 N5 -9.9(7) . . . . ?
C16 N4 C17 C18 153.4(5) . . . . ?
C24 N5 C17 N4 154.7(5) . . . . ?
B1 N5 C17 N4 -8.5(7) . . . . ?
C24 N5 C17 C18 -12.0(5) . . . . ?
B1 N5 C17 C18 -175.2(4) . . . . ?
N4 C17 C18 C23 -159.1(5) . . . . ?
N5 C17 C18 C23 6.2(5) . . . . ?
N4 C17 C18 C19 14.5(9) . . . . ?
N5 C17 C18 C19 179.8(5) . . . . ?
C23 C18 C19 C20 -1.4(8) . . . . ?
C17 C18 C19 C20 -174.3(5) . . . . ?
C18 C19 C20 C21A 0.7(9) . . . . ?
C18 C19 C20 C21 0.7(9) . . . . ?
C19 C20 C21 C22 0.9(10) . . . . ?
C19 C20 C21 Cl6 -177.6(5) . . . . ?
C19 C20 C21A C22 0.9(10) . . . . ?
C20 C21A C22 C23 -1.7(9) . . . . ?
C20 C21 C22 C23 -1.7(9) . . . . ?
Cl6 C21 C22 C23 176.8(4) . . . . ?
C19 C18 C23 C22 0.5(8) . . . . ?
C17 C18 C23 C22 175.0(5) . . . . ?
C19 C18 C23 C24 -173.2(5) . . . . ?
C17 C18 C23 C24 1.3(5) . . . . ?
C21A C22 C23 C18 1.0(8) . . . . ?
C21 C22 C23 C18 1.0(8) . . . . ?
C21A C22 C23 C24 173.2(5) . . . . ?
C21 C22 C23 C24 173.2(5) . . . . ?
C1 N6 C24 N5 8.3(7) . . . . ?
C1 N6 C24 C23 -152.9(5) . . . . ?
C17 N5 C24 N6 -152.4(5) . . . . ?
B1 N5 C24 N6 10.9(7) . . . . ?
C17 N5 C24 C23 12.7(5) . . . . ?
B1 N5 C24 C23 176.0(4) . . . . ?
C18 C23 C24 N6 155.6(5) . . . . ?
C22 C23 C24 N6 -17.5(9) . . . . ?
C18 C23 C24 N5 -8.2(5) . . . . ?
C22 C23 C24 N5 178.7(5) . . . . ?
C9 N3 B1 N5 138.9(4) . . . . ?
C16 N3 B1 N5 -25.7(6) . . . . ?
C9 N3 B1 N1 26.2(6) . . . . ?
C16 N3 B1 N1 -138.4(4) . . . . ?
C9 N3 B1 Cl1 -97.0(5) . . . . ?
C16 N3 B1 Cl1 98.4(5) . . . . ?
C17 N5 B1 N3 24.6(6) . . . . ?
C24 N5 B1 N3 -136.8(4) . . . . ?
C17 N5 B1 N1 136.9(4) . . . . ?
C24 N5 B1 N1 -24.6(6) . . . . ?
C17 N5 B1 Cl1 -99.4(5) . . . . ?
C24 N5 B1 Cl1 99.2(5) . . . . ?
C1 N1 B1 N3 135.8(4) . . . . ?
C8 N1 B1 N3 -25.6(6) . . . . ?
C1 N1 B1 N5 23.0(6) . . . . ?
C8 N1 B1 N5 -138.4(4) . . . . ?
C1 N1 B1 Cl1 -100.9(5) . . . . ?
C8 N1 B1 Cl1 97.7(5) . . . . ?

_refine_diff_density_max         0.776
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.070



_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_d1802_a
_database_code_depnum_ccdc_archive 'CCDC 2051783'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        Cl-bF3BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H9 B Cl F3 N6'
_chemical_formula_sum            'C24 H9 B Cl F3 N6'
_chemical_formula_weight         484.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.6548(9)
_cell_length_b                   15.1757(11)
_cell_length_c                   10.1016(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1940.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4328
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      66.72

_exptl_crystal_description       Block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.263
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9460
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.260
_diffrn_reflns_theta_max         67.100
_diffrn_reflns_theta_full        67.100
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1776
_reflns_number_gt                1589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0137P)²+3.8866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1776
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.79912(9) 0.750000 0.74684(11) 0.0406(3) Uani 1 2 d S T P . .
F1 F 1.0856(2) 0.4223(2) 0.2244(3) 0.0450(11) Uani 0.591(5) 1 d . . P A 1
C4 C 1.0118(3) 0.4619(2) 0.2855(3) 0.0360(7) Uani 0.591(5) 1 d . . P A 1
C4A C 1.0118(3) 0.4619(2) 0.2855(3) 0.0360(7) Uani 0.409(5) 1 d . . P A 2
H4A H 1.069506 0.433868 0.242529 0.043 Uiso 0.409(5) 1 calc R U P A 2
F2 F 0.9303(3) 0.3269(3) 0.2755(4) 0.0359(14) Uani 0.409(5) 1 d . . P A 1
C5 C 0.9195(3) 0.4143(2) 0.3060(3) 0.0351(7) Uani 0.409(5) 1 d . . P A 1
C5A C 0.9195(3) 0.4143(2) 0.3060(3) 0.0351(7) Uani 0.591(5) 1 d . . P A 2
H5A H 0.916639 0.354323 0.279362 0.042 Uiso 0.591(5) 1 calc R U P A 2
C12 C 0.3261(2) 0.7039(3) 0.3921(3) 0.0422(8) Uani 0.5 1 d . . P B 1
H12 H 0.263430 0.673720 0.367196 0.051 Uiso 0.5 1 calc R U P B 1
C12A C 0.3261(2) 0.7039(3) 0.3921(3) 0.0422(8) Uani 0.5 1 d . . P B 2
F3 F 0.2380(3) 0.6654(3) 0.3520(4) 0.0576(12) Uani 0.5 1 d . . P B 2
N1 N 0.9738(3) 0.750000 0.4177(3) 0.0278(8) Uani 1 2 d S T P . .
N2 N 0.82332(19) 0.67266(16) 0.4985(2) 0.0277(6) Uani 1 1 d . . . . .
N3 N 0.65976(19) 0.59724(18) 0.4741(2) 0.0315(6) Uani 1 1 d . . . . .
N4 N 0.6643(3) 0.750000 0.5261(3) 0.0286(8) Uani 1 2 d S T P . .
C1 C 0.9208(2) 0.6748(2) 0.4406(3) 0.0267(6) Uani 1 1 d . . . . .
C2 C 0.9373(2) 0.5863(2) 0.3891(3) 0.0279(6) Uani 1 1 d . . . . .
C3 C 1.0229(2) 0.5480(2) 0.3252(3) 0.0300(7) Uani 1 1 d . . . . .
H3A H 1.086230 0.579897 0.309536 0.036 Uiso 1 1 calc R U . A 1
C6 C 0.8320(2) 0.4520(2) 0.3639(3) 0.0330(7) Uani 1 1 d . . . . .
H6A H 0.767946 0.420103 0.374049 0.040 Uiso 1 1 calc R U . A 1
C7 C 0.8412(2) 0.5388(2) 0.4070(3) 0.0289(7) Uani 1 1 d . . . . .
C8 C 0.7664(2) 0.5985(2) 0.4687(3) 0.0296(7) Uani 1 1 d . . . . .
C9 C 0.6106(2) 0.6746(2) 0.4944(3) 0.0296(7) Uani 1 1 d . . . . .
C10 C 0.5041(2) 0.7031(2) 0.4622(3) 0.0326(7) Uani 1 1 d . . . . .
C11 C 0.4135(2) 0.6557(3) 0.4268(3) 0.0363(8) Uani 1 1 d . . . . .
H11 H 0.412642 0.593067 0.426738 0.044 Uiso 1 1 calc R U . B 1
B1 B 0.7767(4) 0.750000 0.5647(5) 0.0281(10) Uani 1 2 d S T P . .


_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 B1 1.862(5) . ?
F1 C4 1.270(4) . ?
C4 C3 1.373(4) . ?
C4 C5 1.389(5) . ?
C4A C3 1.373(4) . ?
C4A C5A 1.389(5) . ?
C4A H4A 0.9500 . ?
F2 C5 1.369(5) . ?
C5 C6 1.377(4) . ?
C5A C6 1.377(4) . ?
C5A H5A 0.9500 . ?
C12 C11 1.373(5) . ?
C12 C12 1.398(8) 7_575 ?
C12 H12 0.9500 . ?
C12A F3 1.323(5) . ?
C12A C11 1.373(5) . ?
N1 C1 1.343(3) 7_575 ?
N1 C1 1.343(3) . ?
N2 C1 1.366(4) . ?
N2 C8 1.371(4) . ?
N2 B1 1.474(4) . ?
N3 C9 1.344(4) . ?
N3 C8 1.350(4) . ?
N4 C9 1.369(3) 7_575 ?
N4 C9 1.369(3) . ?
N4 B1 1.475(6) . ?
C1 C2 1.456(4) . ?
C2 C3 1.389(4) . ?
C2 C7 1.424(4) . ?
C3 H3A 0.9500 . ?
C6 C7 1.393(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.450(4) . ?
C9 C10 1.453(4) . ?
C10 C11 1.399(4) . ?
C10 C10 1.424(7) 7_575 ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C4 C3 121.2(3) . . ?
F1 C4 C5 116.4(3) . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4A C5A 122.5(3) . . ?
C3 C4A H4A 118.8 . . ?
C5A C4A H4A 118.8 . . ?
F2 C5 C6 125.4(3) . . ?
F2 C5 C4 112.7(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5A C4A 121.6(3) . . ?
C6 C5A H5A 119.2 . . ?
C4A C5A H5A 119.2 . . ?
C11 C12 C12 122.3(2) . 7_575 ?
C11 C12 H12 118.9 . . ?
C12 C12 H12 118.9 7_575 . ?
F3 C12A C11 121.4(4) . . ?
C1 N1 C1 116.2(3) 7_575 . ?
C1 N2 C8 113.6(2) . . ?
C1 N2 B1 122.5(3) . . ?
C8 N2 B1 122.9(3) . . ?
C9 N3 C8 117.2(3) . . ?
C9 N4 C9 113.5(3) 7_575 . ?
C9 N4 B1 122.70(18) 7_575 . ?
C9 N4 B1 122.70(18) . . ?
N1 C1 N2 123.1(3) . . ?
N1 C1 C2 130.6(3) . . ?
N2 C1 C2 105.1(2) . . ?
C3 C2 C7 120.9(3) . . ?
C3 C2 C1 131.6(3) . . ?
C7 C2 C1 107.4(3) . . ?
C4A C3 C2 117.0(3) . . ?
C4 C3 C2 117.0(3) . . ?
C4 C3 H3A 121.5 . . ?
C2 C3 H3A 121.5 . . ?
C5A C6 C7 117.3(3) . . ?
C5 C6 C7 117.3(3) . . ?
C5 C6 H6A 121.3 . . ?
C7 C6 H6A 121.3 . . ?
C6 C7 C2 120.7(3) . . ?
C6 C7 C8 132.1(3) . . ?
C2 C7 C8 107.2(3) . . ?
N3 C8 N2 121.8(3) . . ?
N3 C8 C7 131.4(3) . . ?
N2 C8 C7 105.3(2) . . ?
N3 C9 N4 122.4(3) . . ?
N3 C9 C10 130.9(3) . . ?
N4 C9 C10 105.3(3) . . ?
C11 C10 C10 120.9(2) . 7_575 ?
C11 C10 C9 131.6(3) . . ?
C10 C10 C9 107.33(18) 7_575 . ?
C12A C11 C10 116.8(3) . . ?
C12 C11 C10 116.8(3) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
N2 B1 N2 105.6(4) . 7_575 ?
N2 B1 N4 105.4(2) . . ?
N2 B1 N4 105.4(2) 7_575 . ?
N2 B1 Cl1 112.8(2) . . ?
N2 B1 Cl1 112.8(2) 7_575 . ?
N4 B1 Cl1 114.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C4 C5 F2 10.2(5) . . . . ?
C3 C4 C5 F2 -171.6(3) . . . . ?
F1 C4 C5 C6 -176.0(3) . . . . ?
C3 C4 C5 C6 2.1(5) . . . . ?
C3 C4A C5A C6 2.1(5) . . . . ?
C1 N1 C1 N2 -7.5(5) 7_575 . . . ?
C1 N1 C1 C2 157.4(2) 7_575 . . . ?
C8 N2 C1 N1 156.4(3) . . . . ?
B1 N2 C1 N1 -12.4(4) . . . . ?
C8 N2 C1 C2 -11.9(3) . . . . ?
B1 N2 C1 C2 179.4(3) . . . . ?
N1 C1 C2 C3 15.8(5) . . . . ?
N2 C1 C2 C3 -177.2(3) . . . . ?
N1 C1 C2 C7 -160.4(3) . . . . ?
N2 C1 C2 C7 6.6(3) . . . . ?
C5A C4A C3 C2 0.8(4) . . . . ?
F1 C4 C3 C2 178.8(3) . . . . ?
C5 C4 C3 C2 0.8(4) . . . . ?
C7 C2 C3 C4A -2.6(4) . . . . ?
C1 C2 C3 C4A -178.4(3) . . . . ?
C7 C2 C3 C4 -2.6(4) . . . . ?
C1 C2 C3 C4 -178.4(3) . . . . ?
C4A C5A C6 C7 -2.9(4) . . . . ?
F2 C5 C6 C7 170.0(3) . . . . ?
C4 C5 C6 C7 -2.9(4) . . . . ?
C5A C6 C7 C2 1.1(4) . . . . ?
C5 C6 C7 C2 1.1(4) . . . . ?
C5A C6 C7 C8 178.7(3) . . . . ?
C5 C6 C7 C8 178.7(3) . . . . ?
C3 C2 C7 C6 1.7(4) . . . . ?
C1 C2 C7 C6 178.4(2) . . . . ?
C3 C2 C7 C8 -176.4(2) . . . . ?
C1 C2 C7 C8 0.3(3) . . . . ?
C9 N3 C8 N2 7.9(4) . . . . ?
C9 N3 C8 C7 -156.2(3) . . . . ?
C1 N2 C8 N3 -155.6(3) . . . . ?
B1 N2 C8 N3 13.1(4) . . . . ?
C1 N2 C8 C7 12.1(3) . . . . ?
B1 N2 C8 C7 -179.2(3) . . . . ?
C6 C7 C8 N3 -18.9(5) . . . . ?
C2 C7 C8 N3 158.9(3) . . . . ?
C6 C7 C8 N2 175.1(3) . . . . ?
C2 C7 C8 N2 -7.1(3) . . . . ?
C8 N3 C9 N4 -8.6(4) . . . . ?
C8 N3 C9 C10 156.2(3) . . . . ?
C9 N4 C9 N3 156.6(2) 7_575 . . . ?
B1 N4 C9 N3 -11.6(5) . . . . ?
C9 N4 C9 C10 -11.6(4) 7_575 . . . ?
B1 N4 C9 C10 -179.8(3) . . . . ?
N3 C9 C10 C11 15.5(5) . . . . ?
N4 C9 C10 C11 -177.8(3) . . . . ?
N3 C9 C10 C10 -160.1(3) . . . 7_575 ?
N4 C9 C10 C10 6.6(2) . . . 7_575 ?
F3 C12A C11 C10 177.3(3) . . . . ?
C12 C12 C11 C10 -0.2(3) 7_575 . . . ?
C10 C10 C11 C12A 0.2(3) 7_575 . . . ?
C9 C10 C11 C12A -174.9(3) . . . . ?
C10 C10 C11 C12 0.2(3) 7_575 . . . ?
C9 C10 C11 C12 -174.9(3) . . . . ?
C1 N2 B1 N2 27.8(5) . . . 7_575 ?
C8 N2 B1 N2 -140.0(2) . . . 7_575 ?
C1 N2 B1 N4 139.1(3) . . . . ?
C8 N2 B1 N4 -28.6(4) . . . . ?
C1 N2 B1 Cl1 -95.8(3) . . . . ?
C8 N2 B1 Cl1 96.5(3) . . . . ?
C9 N4 B1 N2 -139.3(3) 7_575 . . . ?
C9 N4 B1 N2 27.9(4) . . . . ?
C9 N4 B1 N2 -27.9(4) 7_575 . . 7_575 ?
C9 N4 B1 N2 139.3(3) . . . 7_575 ?
C9 N4 B1 Cl1 96.4(3) 7_575 . . . ?
C9 N4 B1 Cl1 -96.4(3) . . . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.056



_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_d19199_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2051784'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2020-12-21 deposited with the CCDC.	2021-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Cl-aCl3BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H8.07 B Cl3.90 N6'
_chemical_formula_weight         529.63

# start Validation Reply Form
_vrf_PLAT250_d19199_a_sq         
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.1 Note  
RESPONSE: Molecule B might be very slightly disordered over the 
crystallographic mirror plane but the ordered anisotropic model was
retained for this analysis.
;
# end Validation Reply Form

# start Validation Reply Form
_vrf_PLAT605_d19199_a_sq         
;
PROBLEM: Largest Solvent Accessible VOID in the Structure       449 A**3   
RESPONSE: During the 
refinement of the structure, electron density peaks were located 
that were believed to be highly disordered 
solvent molecules (benzene and hexanes were the solvents used). 
Attempts made to model the solvent molecule were not successful. 
The SQUEEZE (Spek, 2015) option in PLATON (Spek, 2009) indicated there 
was a large solvent cavity of 449 A**3. In the final cycles of 
refinement, this contribution of 127 electrons to the 
electron density was removed from the observed data. The 
density, the F(000) value, the molecular weight and the formula are 
given without taking into account the results obtained with the 
SQUEEZE (Spek, 2015) option PLATON (Spek, 2009). Similar treatments 
of disordered solvent molecules were carried out in the recent  
structure determination given below.
References: 

Spek, A. L. (2015). Acta Cryst. C71, 9--18.
  
Spek, A. L. (2009). <i>Acta Cryst.</i> <b>D65</b>, 148--155.
  
R. Manohar, M. Harikrishna, S. H. Etti, C. Ramanathan and K. Gunasekaran
Acta Cryst. (2019). E75, 562-564
  
R. Vishnupriya, M. Venkateshan, J. Suresh, R. V. Sumesh, R. R. Kumar and 
P. L. N. Lakshman
Acta Cryst. (2019). E75, 189-193

K. B. Polyanskii, K. A. Alekseeva, P. A. Kumandin, Z. Atioglu, M. Akkurt 
and F. A. A. Toze
Acta Cryst. (2019). E75, 342-345
  
T. I. Ayudhya, A. L. Rheingold and N. N. Dingra
Acta Cryst. (2019). E75, 543-546
  
S. Syed Abuthahir, M. NizamMohideen, V. Viswanathan, T. Abiraman 
and S. Balasubramanian
Acta Cryst. (2019). E75, 655-661
;
# end Validation Reply Form

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   22.9423(9)
_cell_length_b                   15.4999(6)
_cell_length_c                   16.4607(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.218(1)
_cell_angle_gamma                90
_cell_volume                     5338.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.31

_exptl_crystal_description       Block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             2123
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.457
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46518
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.356
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6375
_reflns_number_gt                3847
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       APEX3
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0878P)²+10.7840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6375
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.2063
_refine_ls_wR_factor_gt          0.1665
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cl1A Cl 0.76496(5) 0.500000 0.19955(6) 0.0421(3) Uani 1 2 d S T P . .
C3A C 0.71209(19) 0.3013(3) -0.1359(2) 0.0654(11) Uani 0.717(4) 1 d . . P A 1
C6A C 0.6410(2) 0.2119(3) -0.0579(3) 0.0645(11) Uani 0.264(5) 1 d . . P B 1
C11A C 0.49901(16) 0.4075(3) 0.1364(2) 0.0591(10) Uani 0.500(4) 1 d . . P C 1
Cl2A Cl 0.75925(7) 0.35080(12) -0.17762(8) 0.0756(7) Uani 0.717(4) 1 d . . P A
1
Cl3A Cl 0.6030(3) 0.1524(3) -0.0167(4) 0.097(2) Uani 0.264(5) 1 d . . P B 1
Cl4A Cl 0.50630(9) 0.30032(16) 0.15472(14) 0.0742(9) Uani 0.500(4) 1 d . . P C
1
C3C C 0.71209(19) 0.3013(3) -0.1359(2) 0.0654(11) Uani 0.283(4) 1 d . . P A 2
H3CA H 0.735700 0.331296 -0.162791 0.078 Uiso 0.283(4) 1 calc R U P A 2
C6C C 0.6410(2) 0.2119(3) -0.0579(3) 0.0645(11) Uani 0.736(5) 1 d . . P B 2
H6CA H 0.616683 0.181223 -0.032601 0.077 Uiso 0.736(5) 1 calc R U P B 2
C11C C 0.49901(16) 0.4075(3) 0.1364(2) 0.0591(10) Uani 0.500(4) 1 d . . P C 2
N1A N 0.72564(18) 0.500000 -0.0602(2) 0.0498(10) Uani 1 2 d S T P . .
N2A N 0.68949(12) 0.42399(17) 0.03570(15) 0.0397(6) Uani 1 1 d . . . . .
N3A N 0.61209(13) 0.35068(17) 0.07127(17) 0.0446(6) Uani 1 1 d . . . . .
N4A N 0.63152(17) 0.500000 0.1011(2) 0.0374(8) Uani 1 2 d S T P . .
C1A C 0.71104(15) 0.4260(2) -0.03005(19) 0.0447(8) Uani 1 1 d . . . . .
C2A C 0.69869(16) 0.3405(2) -0.0688(2) 0.0504(9) Uani 1 1 d . . . . .
C4A C 0.6908(2) 0.2196(3) -0.1621(3) 0.0762(14) Uani 1 1 d . . . . .
H4A H 0.700252 0.192703 -0.207151 0.091 Uiso 1 1 calc R U . A 1
C5A C 0.6558(2) 0.1750(3) -0.1247(3) 0.0758(14) Uani 1 1 d . . . . .
H5A H 0.641526 0.118171 -0.144745 0.091 Uiso 1 1 calc R U . B 1
C7A C 0.66303(16) 0.2945(2) -0.0297(2) 0.0490(8) Uani 1 1 d . . . . .
C8A C 0.65442(15) 0.3527(2) 0.03414(19) 0.0438(7) Uani 1 1 d . . . . .
C9A C 0.59901(14) 0.4262(2) 0.10001(18) 0.0398(7) Uani 1 1 d . . . . .
C10A C 0.54479(15) 0.4543(2) 0.11847(19) 0.0439(7) Uani 1 1 d . . . . .
C12A C 0.45486(17) 0.4544(3) 0.1555(2) 0.0658(12) Uani 1 1 d . . . . .
H12A H 0.423751 0.424593 0.168966 0.079 Uiso 1 1 calc R U . C 1
B1A B 0.6923(2) 0.500000 0.0911(3) 0.0373(10) Uani 1 2 d S T P . .
Cl1B Cl 0.66257(6) 0.500000 0.31313(7) 0.0486(3) Uani 1 2 d S T P . .
C3B C 0.7955(3) 0.6998(5) 0.6496(3) 0.128(3) Uani 0.495(5) 1 d . . P D 1
C6B C 0.6791(4) 0.7921(4) 0.5607(4) 0.116(3) Uani 0.451(6) 1 d . . P E 1
C11B C 0.4276(2) 0.5921(4) 0.3671(3) 0.0916(17) Uani 0.478(5) 1 d . . P F 1
Cl2B Cl 0.85941(12) 0.6641(2) 0.70085(15) 0.1047(15) Uani 0.495(5) 1 d . . P D
1
Cl3B Cl 0.6288(2) 0.84703(19) 0.5245(3) 0.1050(17) Uani 0.451(6) 1 d . . P E 1
Cl4B Cl 0.42247(13) 0.6902(2) 0.35587(17) 0.0962(14) Uani 0.478(5) 1 d . . P F
1
C3D C 0.7955(3) 0.6998(5) 0.6496(3) 0.128(3) Uani 0.505(5) 1 d . . P D 2
H3D H 0.834630 0.669821 0.679532 0.154 Uiso 0.505(5) 1 calc R U P D 2
C6D C 0.6791(4) 0.7921(4) 0.5607(4) 0.116(3) Uani 0.549(6) 1 d . . P E 2
H6D H 0.640243 0.822998 0.531721 0.140 Uiso 0.549(6) 1 calc R U P E 2
C11D C 0.4276(2) 0.5921(4) 0.3671(3) 0.0916(17) Uani 0.522(5) 1 d . . P F 2
N1B N 0.7670(2) 0.500000 0.5745(3) 0.0699(14) Uani 1 2 d S T P . .
N2B N 0.67737(14) 0.5760(2) 0.47379(17) 0.0500(7) Uani 1 1 d . . . . .
N3B N 0.57822(18) 0.6485(2) 0.4300(2) 0.0603(8) Uani 1 1 d . . . . .
N4B N 0.58217(19) 0.500000 0.4019(2) 0.0458(9) Uani 1 2 d S T P . .
C1B C 0.73633(19) 0.5736(3) 0.5433(2) 0.0624(11) Uani 1 1 d . . . . .
C2B C 0.7442(3) 0.6611(4) 0.5798(3) 0.0836(16) Uani 1 1 d . . . . .
C4B C 0.7877(5) 0.7817(6) 0.6733(5) 0.155(5) Uani 1 1 d . . . . .
H4B H 0.821794 0.808259 0.721528 0.186 Uiso 1 1 calc R U . D 1
C5B C 0.7307(6) 0.8282(5) 0.6288(6) 0.167(5) Uani 1 1 d . . . . .
H5B H 0.727911 0.885926 0.646231 0.200 Uiso 1 1 calc R U . E 1
C7B C 0.6863(3) 0.7060(3) 0.5353(3) 0.0768(14) Uani 1 1 d . . . . .
C8B C 0.6417(2) 0.6479(2) 0.4707(2) 0.0575(10) Uani 1 1 d . . . . .
C9B C 0.54896(18) 0.5736(3) 0.4010(2) 0.0537(9) Uani 1 1 d . . . . .
C10B C 0.48450(17) 0.5448(3) 0.3819(2) 0.0635(11) Uani 1 1 d . . . . .
C12B C 0.3739(2) 0.5458(4) 0.3513(3) 0.108(3) Uani 1 1 d . . . . .
H12B H 0.335096 0.575584 0.339854 0.129 Uiso 1 1 calc R U . F 1
B1B B 0.6498(3) 0.500000 0.4172(3) 0.0442(12) Uani 1 2 d S T P . .


_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
Cl1A B1A 1.877(5) . ?
C3A C4A 1.362(6) . ?
C3A C2A 1.401(5) . ?
C3A Cl2A 1.686(5) . ?
C6A C7A 1.385(5) . ?
C6A C5A 1.400(6) . ?
C6A Cl3A 1.599(7) . ?
C11A C12A 1.384(5) . ?
C11A C10A 1.403(5) . ?
C11A Cl4A 1.684(5) . ?
C3C C4A 1.362(6) . ?
C3C C2A 1.401(5) . ?
C3C H3CA 0.9500 . ?
C6C C7A 1.385(5) . ?
C6C C5A 1.400(6) . ?
C6C H6CA 0.9500 . ?
C11C C12A 1.384(5) . ?
C11C C10A 1.403(5) . ?
N1A C1A 1.345(4) 6_565 ?
N1A C1A 1.345(4) . ?
N2A C8A 1.361(4) . ?
N2A C1A 1.362(4) . ?
N2A B1A 1.475(4) . ?
N3A C9A 1.341(4) . ?
N3A C8A 1.343(4) . ?
N4A C9A 1.362(3) . ?
N4A C9A 1.362(3) 6_565 ?
N4A B1A 1.470(6) . ?
C1A C2A 1.448(5) . ?
C2A C7A 1.422(5) . ?
C4A C5A 1.381(7) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C7A C8A 1.459(4) . ?
C9A C10A 1.463(4) . ?
C10A C10A 1.418(7) 6_565 ?
C12A C12A 1.412(9) 6_565 ?
C12A H12A 0.9500 . ?
Cl1B B1B 1.852(5) . ?
C3B C4B 1.361(11) . ?
C3B C2B 1.398(7) . ?
C3B Cl2B 1.468(9) . ?
C6B Cl3B 1.359(9) . ?
C6B C5B 1.372(11) . ?
C6B C7B 1.428(8) . ?
C11B C12B 1.356(7) . ?
C11B C10B 1.427(6) . ?
C11B Cl4B 1.531(7) . ?
C3D C4B 1.361(11) . ?
C3D C2B 1.398(7) . ?
C3D H3D 0.9500 . ?
C6D C5B 1.372(11) . ?
C6D C7B 1.428(8) . ?
C6D H6D 0.9500 . ?
C11D C12B 1.356(7) . ?
C11D C10B 1.427(6) . ?
N1B C1B 1.327(5) 6_565 ?
N1B C1B 1.327(5) . ?
N2B C1B 1.367(5) . ?
N2B C8B 1.371(5) . ?
N2B B1B 1.474(4) . ?
N3B C9B 1.328(5) . ?
N3B C8B 1.330(5) . ?
N4B C9B 1.369(4) 6_565 ?
N4B C9B 1.369(4) . ?
N4B B1B 1.466(7) . ?
C1B C2B 1.464(6) . ?
C2B C7B 1.411(7) . ?
C4B C5B 1.407(13) . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
C7B C8B 1.447(6) . ?
C9B C10B 1.450(5) . ?
C10B C10B 1.390(9) 6_565 ?
C12B C12B 1.421(12) 6_565 ?
C12B H12B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4A C3A C2A 119.1(4) . . ?
C4A C3A Cl2A 120.1(3) . . ?
C2A C3A Cl2A 120.6(4) . . ?
C7A C6A C5A 118.0(4) . . ?
C7A C6A Cl3A 125.4(4) . . ?
C5A C6A Cl3A 116.6(4) . . ?
C12A C11A C10A 117.2(4) . . ?
C12A C11A Cl4A 120.4(3) . . ?
C10A C11A Cl4A 121.3(3) . . ?
C4A C3C C2A 119.1(4) . . ?
C4A C3C H3CA 120.4 . . ?
C2A C3C H3CA 120.4 . . ?
C7A C6C C5A 118.0(4) . . ?
C7A C6C H6CA 121.0 . . ?
C5A C6C H6CA 121.0 . . ?
C12A C11C C10A 117.2(4) . . ?
C1A N1A C1A 116.9(4) 6_565 . ?
C8A N2A C1A 114.1(3) . . ?
C8A N2A B1A 122.4(3) . . ?
C1A N2A B1A 122.3(3) . . ?
C9A N3A C8A 116.6(3) . . ?
C9A N4A C9A 114.3(4) . 6_565 ?
C9A N4A B1A 122.56(18) . . ?
C9A N4A B1A 122.57(18) 6_565 . ?
N1A C1A N2A 122.6(3) . . ?
N1A C1A C2A 130.6(3) . . ?
N2A C1A C2A 105.0(3) . . ?
C3C C2A C7A 119.5(4) . . ?
C3A C2A C7A 119.5(4) . . ?
C3C C2A C1A 132.7(4) . . ?
C3A C2A C1A 132.7(4) . . ?
C7A C2A C1A 107.7(3) . . ?
C3C C4A C5A 121.5(4) . . ?
C3A C4A C5A 121.5(4) . . ?
C3A C4A H4A 119.2 . . ?
C5A C4A H4A 119.2 . . ?
C4A C5A C6A 121.2(4) . . ?
C4A C5A C6C 121.2(4) . . ?
C4A C5A H5A 119.4 . . ?
C6A C5A H5A 119.4 . . ?
C6C C7A C2A 120.7(3) . . ?
C6A C7A C2A 120.7(3) . . ?
C6C C7A C8A 132.4(4) . . ?
C6A C7A C8A 132.4(4) . . ?
C2A C7A C8A 106.8(3) . . ?
N3A C8A N2A 122.9(3) . . ?
N3A C8A C7A 130.6(3) . . ?
N2A C8A C7A 105.2(3) . . ?
N3A C9A N4A 122.5(3) . . ?
N3A C9A C10A 131.7(3) . . ?
N4A C9A C10A 104.8(3) . . ?
C11A C10A C10A 121.1(2) . 6_565 ?
C11C C10A C9A 131.6(3) . . ?
C11A C10A C9A 131.6(3) . . ?
C10A C10A C9A 107.31(18) 6_565 . ?
C11A C12A C12A 121.7(2) . 6_565 ?
C11A C12A H12A 119.1 . . ?
C12A C12A H12A 119.1 6_565 . ?
N4A B1A N2A 105.4(3) . . ?
N4A B1A N2A 105.4(3) . 6_565 ?
N2A B1A N2A 106.0(3) . 6_565 ?
N4A B1A Cl1A 114.0(3) . . ?
N2A B1A Cl1A 112.6(2) . . ?
N2A B1A Cl1A 112.6(2) 6_565 . ?
C4B C3B C2B 118.1(8) . . ?
C4B C3B Cl2B 113.8(6) . . ?
C2B C3B Cl2B 128.1(7) . . ?
Cl3B C6B C5B 113.3(7) . . ?
Cl3B C6B C7B 129.5(6) . . ?
C5B C6B C7B 117.1(8) . . ?
C12B C11B C10B 117.2(6) . . ?
C12B C11B Cl4B 118.9(4) . . ?
C10B C11B Cl4B 123.4(4) . . ?
C4B C3D C2B 118.1(8) . . ?
C4B C3D H3D 121.0 . . ?
C2B C3D H3D 121.0 . . ?
C5B C6D C7B 117.1(8) . . ?
C5B C6D H6D 121.4 . . ?
C7B C6D H6D 121.4 . . ?
C12B C11D C10B 117.2(6) . . ?
C1B N1B C1B 118.4(5) 6_565 . ?
C1B N2B C8B 115.1(3) . . ?
C1B N2B B1B 121.9(3) . . ?
C8B N2B B1B 122.1(3) . . ?
C9B N3B C8B 117.5(3) . . ?
C9B N4B C9B 112.9(4) 6_565 . ?
C9B N4B B1B 123.2(2) 6_565 . ?
C9B N4B B1B 123.2(2) . . ?
N1B C1B N2B 122.2(4) . . ?
N1B C1B C2B 132.8(4) . . ?
N2B C1B C2B 103.4(4) . . ?
C3D C2B C7B 120.7(6) . . ?
C3B C2B C7B 120.7(6) . . ?
C3D C2B C1B 131.0(7) . . ?
C3B C2B C1B 131.0(7) . . ?
C7B C2B C1B 108.2(4) . . ?
C3D C4B C5B 122.1(8) . . ?
C3B C4B C5B 122.1(8) . . ?
C3B C4B H4B 118.9 . . ?
C5B C4B H4B 118.9 . . ?
C6D C5B C4B 121.5(8) . . ?
C6B C5B C4B 121.5(8) . . ?
C6B C5B H5B 119.2 . . ?
C4B C5B H5B 119.2 . . ?
C2B C7B C6B 120.4(5) . . ?
C2B C7B C6D 120.4(5) . . ?
C2B C7B C8B 107.8(4) . . ?
C6B C7B C8B 131.7(6) . . ?
C6D C7B C8B 131.7(6) . . ?
N3B C8B N2B 122.6(3) . . ?
N3B C8B C7B 131.6(4) . . ?
N2B C8B C7B 104.3(4) . . ?
N3B C9B N4B 121.9(3) . . ?
N3B C9B C10B 131.8(3) . . ?
N4B C9B C10B 105.1(3) . . ?
C10B C10B C11B 120.8(3) 6_565 . ?
C10B C10B C11D 120.8(3) 6_565 . ?
C10B C10B C9B 107.9(2) 6_565 . ?
C11B C10B C9B 131.2(4) . . ?
C11D C10B C9B 131.2(4) . . ?
C11D C12B C12B 121.9(3) . 6_565 ?
C11B C12B C12B 121.9(3) . 6_565 ?
C11B C12B H12B 119.0 . . ?
C12B C12B H12B 119.0 6_565 . ?
N4B B1B N2B 105.0(3) . . ?
N4B B1B N2B 105.0(3) . 6_565 ?
N2B B1B N2B 106.1(4) . 6_565 ?
N4B B1B Cl1B 113.5(3) . . ?
N2B B1B Cl1B 113.3(2) . . ?
N2B B1B Cl1B 113.3(2) 6_565 . ?

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
C1A N1A C1A N2A -7.6(6) 6_565 . . . ?
C1A N1A C1A C2A 155.3(3) 6_565 . . . ?
C8A N2A C1A N1A 155.5(3) . . . . ?
B1A N2A C1A N1A -12.3(5) . . . . ?
C8A N2A C1A C2A -11.1(3) . . . . ?
B1A N2A C1A C2A -178.9(3) . . . . ?
C4A C3C C2A C7A -0.3(5) . . . . ?
C4A C3C C2A C1A -176.1(4) . . . . ?
C4A C3A C2A C7A -0.3(5) . . . . ?
Cl2A C3A C2A C7A -175.0(3) . . . . ?
C4A C3A C2A C1A -176.1(4) . . . . ?
Cl2A C3A C2A C1A 9.2(5) . . . . ?
N1A C1A C2A C3C 17.8(6) . . . . ?
N2A C1A C2A C3C -177.1(4) . . . . ?
N1A C1A C2A C3A 17.8(6) . . . . ?
N2A C1A C2A C3A -177.1(4) . . . . ?
N1A C1A C2A C7A -158.4(4) . . . . ?
N2A C1A C2A C7A 6.8(3) . . . . ?
C2A C3C C4A C5A 0.7(6) . . . . ?
C2A C3A C4A C5A 0.7(6) . . . . ?
Cl2A C3A C4A C5A 175.4(3) . . . . ?
C3A C4A C5A C6A -0.3(6) . . . . ?
C3C C4A C5A C6C -0.3(6) . . . . ?
C7A C6A C5A C4A -0.5(6) . . . . ?
Cl3A C6A C5A C4A -177.4(4) . . . . ?
C7A C6C C5A C4A -0.5(6) . . . . ?
C5A C6C C7A C2A 0.9(5) . . . . ?
C5A C6C C7A C8A 176.9(4) . . . . ?
C5A C6A C7A C2A 0.9(5) . . . . ?
Cl3A C6A C7A C2A 177.5(4) . . . . ?
C5A C6A C7A C8A 176.9(4) . . . . ?
Cl3A C6A C7A C8A -6.5(6) . . . . ?
C3C C2A C7A C6C -0.5(5) . . . . ?
C1A C2A C7A C6C 176.3(3) . . . . ?
C3A C2A C7A C6A -0.5(5) . . . . ?
C1A C2A C7A C6A 176.3(3) . . . . ?
C3C C2A C7A C8A -177.5(3) . . . . ?
C3A C2A C7A C8A -177.5(3) . . . . ?
C1A C2A C7A C8A -0.7(3) . . . . ?
C9A N3A C8A N2A 8.9(4) . . . . ?
C9A N3A C8A C7A -155.5(3) . . . . ?
C1A N2A C8A N3A -157.1(3) . . . . ?
B1A N2A C8A N3A 10.7(5) . . . . ?
C1A N2A C8A C7A 10.7(3) . . . . ?
B1A N2A C8A C7A 178.5(3) . . . . ?
C6C C7A C8A N3A -15.6(6) . . . . ?
C6A C7A C8A N3A -15.6(6) . . . . ?
C2A C7A C8A N3A 160.8(3) . . . . ?
C6C C7A C8A N2A 177.9(3) . . . . ?
C6A C7A C8A N2A 177.9(3) . . . . ?
C2A C7A C8A N2A -5.6(3) . . . . ?
C8A N3A C9A N4A -7.0(4) . . . . ?
C8A N3A C9A C10A 159.3(3) . . . . ?
C9A N4A C9A N3A 157.0(2) 6_565 . . . ?
B1A N4A C9A N3A -14.6(5) . . . . ?
C9A N4A C9A C10A -12.5(4) 6_565 . . . ?
B1A N4A C9A C10A 175.9(3) . . . . ?
C12A C11C C10A C10A -1.1(4) . . . 6_565 ?
C12A C11C C10A C9A 177.0(3) . . . . ?
C12A C11A C10A C10A -1.1(4) . . . 6_565 ?
Cl4A C11A C10A C10A -168.85(17) . . . 6_565 ?
C12A C11A C10A C9A 177.0(3) . . . . ?
Cl4A C11A C10A C9A 9.3(5) . . . . ?
N3A C9A C10A C11C 20.6(5) . . . . ?
N4A C9A C10A C11C -171.2(3) . . . . ?
N3A C9A C10A C11A 20.6(5) . . . . ?
N4A C9A C10A C11A -171.2(3) . . . . ?
N3A C9A C10A C10A -161.1(3) . . . 6_565 ?
N4A C9A C10A C10A 7.1(2) . . . 6_565 ?
C10A C11C C12A C12A 1.2(4) . . . 6_565 ?
C10A C11A C12A C12A 1.2(4) . . . 6_565 ?
Cl4A C11A C12A C12A 168.98(16) . . . 6_565 ?
C9A N4A B1A N2A 29.5(4) . . . . ?
C9A N4A B1A N2A -141.4(3) 6_565 . . . ?
C9A N4A B1A N2A 141.4(3) . . . 6_565 ?
C9A N4A B1A N2A -29.5(4) 6_565 . . 6_565 ?
C9A N4A B1A Cl1A -94.5(3) . . . . ?
C9A N4A B1A Cl1A 94.5(3) 6_565 . . . ?
C8A N2A B1A N4A -27.6(4) . . . . ?
C1A N2A B1A N4A 139.2(3) . . . . ?
C8A N2A B1A N2A -139.1(3) . . . 6_565 ?
C1A N2A B1A N2A 27.7(5) . . . 6_565 ?
C8A N2A B1A Cl1A 97.3(3) . . . . ?
C1A N2A B1A Cl1A -95.9(3) . . . . ?
C1B N1B C1B N2B -7.2(7) 6_565 . . . ?
C1B N1B C1B C2B 155.7(3) 6_565 . . . ?
C8B N2B C1B N1B 155.9(4) . . . . ?
B1B N2B C1B N1B -12.9(5) . . . . ?
C8B N2B C1B C2B -11.3(4) . . . . ?
B1B N2B C1B C2B 179.9(3) . . . . ?
C4B C3D C2B C7B 0.2(7) . . . . ?
C4B C3D C2B C1B -175.4(5) . . . . ?
C4B C3B C2B C7B 0.2(7) . . . . ?
Cl2B C3B C2B C7B -177.7(4) . . . . ?
C4B C3B C2B C1B -175.4(5) . . . . ?
Cl2B C3B C2B C1B 6.6(7) . . . . ?
N1B C1B C2B C3D 17.4(7) . . . . ?
N2B C1B C2B C3D -177.5(4) . . . . ?
N1B C1B C2B C3B 17.4(7) . . . . ?
N2B C1B C2B C3B -177.5(4) . . . . ?
N1B C1B C2B C7B -158.7(4) . . . . ?
N2B C1B C2B C7B 6.5(4) . . . . ?
C2B C3D C4B C5B -1.4(10) . . . . ?
C2B C3B C4B C5B -1.4(10) . . . . ?
Cl2B C3B C4B C5B 176.8(6) . . . . ?
C7B C6D C5B C4B -1.7(9) . . . . ?
Cl3B C6B C5B C4B -178.8(6) . . . . ?
C7B C6B C5B C4B -1.7(9) . . . . ?
C3D C4B C5B C6D 2.2(12) . . . . ?
C3B C4B C5B C6B 2.2(12) . . . . ?
C3B C2B C7B C6B 0.2(6) . . . . ?
C1B C2B C7B C6B 176.8(3) . . . . ?
C3D C2B C7B C6D 0.2(6) . . . . ?
C1B C2B C7B C6D 176.8(3) . . . . ?
C3D C2B C7B C8B -176.7(3) . . . . ?
C3B C2B C7B C8B -176.7(3) . . . . ?
C1B C2B C7B C8B -0.1(4) . . . . ?
Cl3B C6B C7B C2B 177.1(4) . . . . ?
C5B C6B C7B C2B 0.5(6) . . . . ?
Cl3B C6B C7B C8B -6.9(7) . . . . ?
C5B C6B C7B C8B 176.5(4) . . . . ?
C5B C6D C7B C2B 0.5(6) . . . . ?
C5B C6D C7B C8B 176.5(4) . . . . ?
C9B N3B C8B N2B 8.2(5) . . . . ?
C9B N3B C8B C7B -155.2(4) . . . . ?
C1B N2B C8B N3B -155.9(3) . . . . ?
B1B N2B C8B N3B 12.9(5) . . . . ?
C1B N2B C8B C7B 11.4(4) . . . . ?
B1B N2B C8B C7B -179.8(3) . . . . ?
C2B C7B C8B N3B 159.3(4) . . . . ?
C6B C7B C8B N3B -17.1(7) . . . . ?
C6D C7B C8B N3B -17.1(7) . . . . ?
C2B C7B C8B N2B -6.3(4) . . . . ?
C6B C7B C8B N2B 177.3(4) . . . . ?
C6D C7B C8B N2B 177.3(4) . . . . ?
C8B N3B C9B N4B -8.4(5) . . . . ?
C8B N3B C9B C10B 156.6(3) . . . . ?
C9B N4B C9B N3B 157.8(2) 6_565 . . . ?
B1B N4B C9B N3B -12.7(5) . . . . ?
C9B N4B C9B C10B -10.8(5) 6_565 . . . ?
B1B N4B C9B C10B 178.8(3) . . . . ?
C12B C11B C10B C10B -1.4(4) . . . 6_565 ?
Cl4B C11B C10B C10B -172.9(2) . . . 6_565 ?
C12B C11B C10B C9B -179.5(3) . . . . ?
Cl4B C11B C10B C9B 8.9(6) . . . . ?
C12B C11D C10B C10B -1.4(4) . . . 6_565 ?
C12B C11D C10B C9B -179.5(3) . . . . ?
N3B C9B C10B C10B -160.7(3) . . . 6_565 ?
N4B C9B C10B C10B 6.2(3) . . . 6_565 ?
N3B C9B C10B C11B 17.6(6) . . . . ?
N4B C9B C10B C11B -175.5(4) . . . . ?
N3B C9B C10B C11D 17.6(6) . . . . ?
N4B C9B C10B C11D -175.5(4) . . . . ?
C10B C11D C12B C12B 1.4(4) . . . 6_565 ?
C10B C11B C12B C12B 1.4(4) . . . 6_565 ?
Cl4B C11B C12B C12B 173.33(19) . . . 6_565 ?
C9B N4B B1B N2B -140.5(3) 6_565 . . . ?
C9B N4B B1B N2B 28.9(5) . . . . ?
C9B N4B B1B N2B -28.9(5) 6_565 . . 6_565 ?
C9B N4B B1B N2B 140.5(3) . . . 6_565 ?
C9B N4B B1B Cl1B 95.3(3) 6_565 . . . ?
C9B N4B B1B Cl1B -95.3(3) . . . . ?
C1B N2B B1B N4B 139.2(3) . . . . ?
C8B N2B B1B N4B -28.8(4) . . . . ?
C1B N2B B1B N2B 28.4(5) . . . 6_565 ?
C8B N2B B1B N2B -139.6(3) . . . 6_565 ?
C1B N2B B1B Cl1B -96.4(3) . . . . ?
C8B N2B B1B Cl1B 95.5(4) . . . . ?

_refine_diff_density_max         0.758
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.061




_exptl_crystal_recrystallization_method 'solvent diffusion'
