# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_d19183_a
_database_code_depnum_ccdc_archive 'CCDC 2087092'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Cl-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 B Cl7 N6'
_chemical_formula_sum            'C24 H6 B Cl7 N6'
_chemical_formula_weight         637.31

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0905(3)
_cell_length_b                   7.4207(2)
_cell_length_c                   25.4832(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.499(1)
_cell_angle_gamma                90
_cell_volume                     2441.51(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9745
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.52

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.844
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6857
_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 Buker 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            29765
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.620
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5627
_reflns_number_gt                4643
_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 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)+(0.0297P)²+1.6014P] 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         5627
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Cl1 Cl 0.61266(3) -0.25212(6) 0.33888(2) 0.02267(10) Uani 1 1 d . . . . .
Cl2 Cl 0.35669(4) 0.78034(8) 0.40922(2) 0.04369(15) Uani 1 1 d . . . . .
Cl3 Cl 0.56239(4) 0.78108(6) 0.49195(2) 0.02881(11) Uani 1 1 d . . . . .
Cl4 Cl 1.20615(3) 0.27834(8) 0.40996(2) 0.03255(12) Uani 1 1 d . . . . .
Cl5 Cl 1.20981(4) 0.16579(8) 0.29151(2) 0.03632(13) Uani 1 1 d . . . . .
Cl6 Cl 0.60107(4) 0.18441(8) 0.02422(2) 0.03525(13) Uani 1 1 d . . . . .
Cl7 Cl 0.37786(4) 0.29260(7) 0.04364(2) 0.02961(11) Uani 1 1 d . . . . .
N1 N 0.60293(10) 0.12122(19) 0.34797(5) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.76205(11) 0.18419(19) 0.40518(5) 0.0180(3) Uani 1 1 d . . . . .
N3 N 0.75978(11) 0.01028(18) 0.32659(5) 0.0160(3) Uani 1 1 d . . . . .
N4 N 0.77374(11) -0.02882(18) 0.23548(5) 0.0162(3) Uani 1 1 d . . . . .
N5 N 0.60861(10) 0.01382(18) 0.26163(5) 0.0157(3) Uani 1 1 d . . . . .
N6 N 0.46588(11) 0.19180(19) 0.27731(5) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.51292(12) 0.2090(2) 0.32816(6) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.50036(13) 0.3456(2) 0.36789(6) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.42609(13) 0.4783(2) 0.36923(7) 0.0218(4) Uani 1 1 d . . . . .
H3A H 0.364233 0.480152 0.343807 0.026 Uiso 1 1 calc R U . . .
C4 C 0.44492(13) 0.6078(3) 0.40879(7) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.53665(14) 0.6072(2) 0.44658(7) 0.0212(4) Uani 1 1 d . . . . .
C6 C 0.61011(13) 0.4745(2) 0.44614(6) 0.0195(4) Uani 1 1 d . . . . .
H6A H 0.671365 0.472502 0.471985 0.023 Uiso 1 1 calc R U . . .
C7 C 0.59169(13) 0.3435(2) 0.40660(6) 0.0175(3) Uani 1 1 d . . . . .
C8 C 0.65912(13) 0.2046(2) 0.39123(6) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.81106(13) 0.0969(2) 0.37044(6) 0.0169(3) Uani 1 1 d . . . . .
C10 C 0.91788(13) 0.1119(2) 0.36181(6) 0.0170(3) Uani 1 1 d . . . . .
C11 C 1.00551(13) 0.1849(2) 0.39292(7) 0.0198(3) Uani 1 1 d . . . . .
H11A H 1.003784 0.225338 0.428131 0.024 Uiso 1 1 calc R U . . .
C12 C 1.09509(13) 0.1966(2) 0.37104(7) 0.0214(4) Uani 1 1 d . . . . .
C13 C 1.09700(13) 0.1438(2) 0.31818(7) 0.0211(4) Uani 1 1 d . . . . .
C14 C 1.01027(13) 0.0728(2) 0.28669(7) 0.0192(3) Uani 1 1 d . . . . .
H14A H 1.011598 0.038938 0.250858 0.023 Uiso 1 1 calc R U . . .
C15 C 0.92098(13) 0.0526(2) 0.30908(6) 0.0168(3) Uani 1 1 d . . . . .
C16 C 0.81682(13) -0.0050(2) 0.28648(6) 0.0163(3) Uani 1 1 d . . . . .
C17 C 0.67076(13) -0.0048(2) 0.22390(6) 0.0158(3) Uani 1 1 d . . . . .
C18 C 0.60872(13) 0.0527(2) 0.17469(6) 0.0167(3) Uani 1 1 d . . . . .
C19 C 0.63564(13) 0.0734(2) 0.12461(6) 0.0181(3) Uani 1 1 d . . . . .
H19A H 0.701449 0.035753 0.117630 0.022 Uiso 1 1 calc R U . . .
C20 C 0.56414(13) 0.1501(2) 0.08542(6) 0.0204(4) Uani 1 1 d . . . . .
C21 C 0.46550(13) 0.2034(2) 0.09516(7) 0.0203(4) Uani 1 1 d . . . . .
C22 C 0.43927(13) 0.1893(2) 0.14553(7) 0.0195(3) Uani 1 1 d . . . . .
H22A H 0.373640 0.228890 0.152255 0.023 Uiso 1 1 calc R U . . .
C23 C 0.51198(13) 0.1152(2) 0.18618(6) 0.0173(3) Uani 1 1 d . . . . .
C24 C 0.51802(12) 0.1023(2) 0.24388(6) 0.0167(3) Uani 1 1 d . . . . .
B1 B 0.64641(15) -0.0245(3) 0.31880(7) 0.0163(4) 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 1.8395(19) . ?
Cl2 C4 1.7253(18) . ?
Cl3 C5 1.7282(18) . ?
Cl4 C12 1.7290(17) . ?
Cl5 C13 1.7321(17) . ?
Cl6 C20 1.7262(17) . ?
Cl7 C21 1.7263(17) . ?
N1 C8 1.368(2) . ?
N1 C1 1.368(2) . ?
N1 B1 1.479(2) . ?
N2 C9 1.343(2) . ?
N2 C8 1.344(2) . ?
N3 C9 1.365(2) . ?
N3 C16 1.366(2) . ?
N3 B1 1.487(2) . ?
N4 C16 1.340(2) . ?
N4 C17 1.343(2) . ?
N5 C17 1.365(2) . ?
N5 C24 1.366(2) . ?
N5 B1 1.487(2) . ?
N6 C1 1.346(2) . ?
N6 C24 1.351(2) . ?
C1 C2 1.461(2) . ?
C2 C3 1.388(2) . ?
C2 C7 1.419(2) . ?
C3 C4 1.385(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.410(3) . ?
C5 C6 1.378(3) . ?
C6 C7 1.392(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.453(2) . ?
C9 C10 1.455(2) . ?
C10 C11 1.392(2) . ?
C10 C15 1.421(2) . ?
C11 C12 1.382(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.407(2) . ?
C13 C14 1.382(2) . ?
C14 C15 1.391(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.454(2) . ?
C17 C18 1.442(2) . ?
C18 C19 1.387(2) . ?
C18 C23 1.424(2) . ?
C19 C20 1.374(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.411(2) . ?
C21 C22 1.386(2) . ?
C22 C23 1.399(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.463(2) . ?

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
C8 N1 C1 113.46(14) . . ?
C8 N1 B1 122.38(14) . . ?
C1 N1 B1 122.84(14) . . ?
C9 N2 C8 116.56(14) . . ?
C9 N3 C16 113.30(14) . . ?
C9 N3 B1 122.41(14) . . ?
C16 N3 B1 122.84(14) . . ?
C16 N4 C17 116.22(14) . . ?
C17 N5 C24 113.65(13) . . ?
C17 N5 B1 122.01(14) . . ?
C24 N5 B1 123.17(14) . . ?
C1 N6 C24 117.10(14) . . ?
N6 C1 N1 122.66(15) . . ?
N6 C1 C2 130.32(15) . . ?
N1 C1 C2 105.26(14) . . ?
C3 C2 C7 120.26(16) . . ?
C3 C2 C1 131.96(16) . . ?
C7 C2 C1 107.20(14) . . ?
C4 C3 C2 117.96(16) . . ?
C4 C3 H3A 121.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 C5 121.59(17) . . ?
C3 C4 Cl2 118.73(14) . . ?
C5 C4 Cl2 119.59(14) . . ?
C6 C5 C4 120.93(16) . . ?
C6 C5 Cl3 118.66(14) . . ?
C4 C5 Cl3 120.30(14) . . ?
C5 C6 C7 117.84(16) . . ?
C5 C6 H6A 121.1 . . ?
C7 C6 H6A 121.1 . . ?
C6 C7 C2 121.39(16) . . ?
C6 C7 C8 130.57(16) . . ?
C2 C7 C8 107.47(14) . . ?
N2 C8 N1 122.99(15) . . ?
N2 C8 C7 129.48(15) . . ?
N1 C8 C7 105.57(14) . . ?
N2 C9 N3 122.88(15) . . ?
N2 C9 C10 129.66(15) . . ?
N3 C9 C10 105.50(13) . . ?
C11 C10 C15 120.65(15) . . ?
C11 C10 C9 131.75(15) . . ?
C15 C10 C9 107.29(14) . . ?
C12 C11 C10 117.97(15) . . ?
C12 C11 H11A 121.0 . . ?
C10 C11 H11A 121.0 . . ?
C11 C12 C13 121.28(16) . . ?
C11 C12 Cl4 118.68(13) . . ?
C13 C12 Cl4 120.05(13) . . ?
C14 C13 C12 121.29(16) . . ?
C14 C13 Cl5 118.69(13) . . ?
C12 C13 Cl5 120.03(13) . . ?
C13 C14 C15 117.94(15) . . ?
C13 C14 H14A 121.0 . . ?
C15 C14 H14A 121.0 . . ?
C14 C15 C10 120.76(15) . . ?
C14 C15 C16 131.76(15) . . ?
C10 C15 C16 107.11(14) . . ?
N4 C16 N3 122.81(15) . . ?
N4 C16 C15 129.77(15) . . ?
N3 C16 C15 105.78(14) . . ?
N4 C17 N5 123.49(14) . . ?
N4 C17 C18 129.14(15) . . ?
N5 C17 C18 105.49(14) . . ?
C19 C18 C23 121.52(15) . . ?
C19 C18 C17 129.85(15) . . ?
C23 C18 C17 108.07(14) . . ?
C20 C19 C18 117.93(16) . . ?
C20 C19 H19A 121.0 . . ?
C18 C19 H19A 121.0 . . ?
C19 C20 C21 121.44(15) . . ?
C19 C20 Cl6 117.32(13) . . ?
C21 C20 Cl6 121.22(13) . . ?
C22 C21 C20 121.01(15) . . ?
C22 C21 Cl7 119.87(14) . . ?
C20 C21 Cl7 119.10(13) . . ?
C21 C22 C23 118.25(16) . . ?
C21 C22 H22A 120.9 . . ?
C23 C22 H22A 120.9 . . ?
C22 C23 C18 119.70(15) . . ?
C22 C23 C24 133.44(16) . . ?
C18 C23 C24 106.45(14) . . ?
N6 C24 N5 121.93(14) . . ?
N6 C24 C23 130.77(15) . . ?
N5 C24 C23 105.32(14) . . ?
N1 B1 N5 105.02(14) . . ?
N1 B1 N3 105.33(14) . . ?
N5 B1 N3 105.13(13) . . ?
N1 B1 Cl1 113.68(12) . . ?
N5 B1 Cl1 113.07(12) . . ?
N3 B1 Cl1 113.74(12) . . ?

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 -8.6(2) . . . . ?
C24 N6 C1 C2 153.94(17) . . . . ?
C8 N1 C1 N6 155.67(15) . . . . ?
B1 N1 C1 N6 -11.5(2) . . . . ?
C8 N1 C1 C2 -10.62(18) . . . . ?
B1 N1 C1 C2 -177.75(14) . . . . ?
N6 C1 C2 C3 12.9(3) . . . . ?
N1 C1 C2 C3 177.74(17) . . . . ?
N6 C1 C2 C7 -158.17(16) . . . . ?
N1 C1 C2 C7 6.66(17) . . . . ?
C7 C2 C3 C4 0.8(2) . . . . ?
C1 C2 C3 C4 -169.30(17) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 Cl2 176.82(13) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
Cl2 C4 C5 C6 -177.87(13) . . . . ?
C3 C4 C5 Cl3 174.70(14) . . . . ?
Cl2 C4 C5 Cl3 -1.7(2) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
Cl3 C5 C6 C7 -174.97(12) . . . . ?
C5 C6 C7 C2 0.0(2) . . . . ?
C5 C6 C7 C8 170.19(16) . . . . ?
C3 C2 C7 C6 -1.0(2) . . . . ?
C1 C2 C7 C6 171.31(14) . . . . ?
C3 C2 C7 C8 -173.24(15) . . . . ?
C1 C2 C7 C8 -0.92(18) . . . . ?
C9 N2 C8 N1 8.9(2) . . . . ?
C9 N2 C8 C7 -152.76(17) . . . . ?
C1 N1 C8 N2 -155.33(15) . . . . ?
B1 N1 C8 N2 11.9(2) . . . . ?
C1 N1 C8 C7 10.08(18) . . . . ?
B1 N1 C8 C7 177.28(14) . . . . ?
C6 C7 C8 N2 -12.3(3) . . . . ?
C2 C7 C8 N2 158.93(16) . . . . ?
C6 C7 C8 N1 -176.44(16) . . . . ?
C2 C7 C8 N1 -5.18(18) . . . . ?
C8 N2 C9 N3 -8.9(2) . . . . ?
C8 N2 C9 C10 152.79(17) . . . . ?
C16 N3 C9 N2 154.83(15) . . . . ?
B1 N3 C9 N2 -11.8(2) . . . . ?
C16 N3 C9 C10 -10.64(18) . . . . ?
B1 N3 C9 C10 -177.26(14) . . . . ?
N2 C9 C10 C11 16.8(3) . . . . ?
N3 C9 C10 C11 -179.08(17) . . . . ?
N2 C9 C10 C15 -156.62(17) . . . . ?
N3 C9 C10 C15 7.48(18) . . . . ?
C15 C10 C11 C12 -0.3(2) . . . . ?
C9 C10 C11 C12 -173.05(17) . . . . ?
C10 C11 C12 C13 2.7(3) . . . . ?
C10 C11 C12 Cl4 -177.42(13) . . . . ?
C11 C12 C13 C14 -2.1(3) . . . . ?
Cl4 C12 C13 C14 177.99(14) . . . . ?
C11 C12 C13 Cl5 178.34(14) . . . . ?
Cl4 C12 C13 Cl5 -1.6(2) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
Cl5 C13 C14 C15 178.67(13) . . . . ?
C13 C14 C15 C10 3.2(2) . . . . ?
C13 C14 C15 C16 175.30(17) . . . . ?
C11 C10 C15 C14 -2.6(3) . . . . ?
C9 C10 C15 C14 171.67(15) . . . . ?
C11 C10 C15 C16 -176.48(15) . . . . ?
C9 C10 C15 C16 -2.17(18) . . . . ?
C17 N4 C16 N3 11.6(2) . . . . ?
C17 N4 C16 C15 -151.65(17) . . . . ?
C9 N3 C16 N4 -157.39(15) . . . . ?
B1 N3 C16 N4 9.2(2) . . . . ?
C9 N3 C16 C15 9.32(18) . . . . ?
B1 N3 C16 C15 175.88(15) . . . . ?
C14 C15 C16 N4 -11.4(3) . . . . ?
C10 C15 C16 N4 161.47(17) . . . . ?
C14 C15 C16 N3 -176.85(18) . . . . ?
C10 C15 C16 N3 -3.97(18) . . . . ?
C16 N4 C17 N5 -10.5(2) . . . . ?
C16 N4 C17 C18 151.60(17) . . . . ?
C24 N5 C17 N4 156.43(15) . . . . ?
B1 N5 C17 N4 -11.6(2) . . . . ?
C24 N5 C17 C18 -9.21(18) . . . . ?
B1 N5 C17 C18 -177.20(14) . . . . ?
N4 C17 C18 C19 10.4(3) . . . . ?
N5 C17 C18 C19 174.90(17) . . . . ?
N4 C17 C18 C23 -160.90(16) . . . . ?
N5 C17 C18 C23 3.64(18) . . . . ?
C23 C18 C19 C20 -2.5(2) . . . . ?
C17 C18 C19 C20 -172.79(17) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
C18 C19 C20 Cl6 177.08(13) . . . . ?
C19 C20 C21 C22 3.6(3) . . . . ?
Cl6 C20 C21 C22 -174.62(14) . . . . ?
C19 C20 C21 Cl7 -178.03(14) . . . . ?
Cl6 C20 C21 Cl7 3.8(2) . . . . ?
C20 C21 C22 C23 -2.1(3) . . . . ?
Cl7 C21 C22 C23 179.56(13) . . . . ?
C21 C22 C23 C18 -1.6(2) . . . . ?
C21 C22 C23 C24 169.95(17) . . . . ?
C19 C18 C23 C22 4.0(2) . . . . ?
C17 C18 C23 C22 176.14(15) . . . . ?
C19 C18 C23 C24 -169.60(15) . . . . ?
C17 C18 C23 C24 2.53(18) . . . . ?
C1 N6 C24 N5 7.8(2) . . . . ?
C1 N6 C24 C23 -153.73(17) . . . . ?
C17 N5 C24 N6 -154.85(15) . . . . ?
B1 N5 C24 N6 13.0(2) . . . . ?
C17 N5 C24 C23 10.76(18) . . . . ?
B1 N5 C24 C23 178.59(14) . . . . ?
C22 C23 C24 N6 -16.2(3) . . . . ?
C18 C23 C24 N6 156.10(17) . . . . ?
C22 C23 C24 N5 179.92(18) . . . . ?
C18 C23 C24 N5 -7.73(18) . . . . ?
C8 N1 B1 N5 -138.63(15) . . . . ?
C1 N1 B1 N5 27.4(2) . . . . ?
C8 N1 B1 N3 -27.9(2) . . . . ?
C1 N1 B1 N3 138.09(15) . . . . ?
C8 N1 B1 Cl1 97.26(16) . . . . ?
C1 N1 B1 Cl1 -96.74(16) . . . . ?
C17 N5 B1 N1 138.60(15) . . . . ?
C24 N5 B1 N1 -28.2(2) . . . . ?
C17 N5 B1 N3 27.7(2) . . . . ?
C24 N5 B1 N3 -139.09(15) . . . . ?
C17 N5 B1 Cl1 -96.91(16) . . . . ?
C24 N5 B1 Cl1 96.26(17) . . . . ?
C9 N3 B1 N1 27.9(2) . . . . ?
C16 N3 B1 N1 -137.42(15) . . . . ?
C9 N3 B1 N5 138.57(15) . . . . ?
C16 N3 B1 N5 -26.8(2) . . . . ?
C9 N3 B1 Cl1 -97.20(17) . . . . ?
C16 N3 B1 Cl1 97.44(16) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.056



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene/heptane'
####################################################################### 
# 
# 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_d2026
_database_code_depnum_ccdc_archive 'CCDC 2087095'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        PhO-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H11 B Cl6 N6 O'
_chemical_formula_sum            'C30 H11 B Cl6 N6 O'
_chemical_formula_weight         694.96

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_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                   13.1340(6)
_cell_length_b                   14.9016(6)
_cell_length_c                   14.5799(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.515(3)
_cell_angle_gamma                90
_cell_volume                     2835.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5798
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      63.54

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    5.859
_shelx_estimated_absorpt_T_min   0.281
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5026
_exptl_absorpt_correction_T_max  0.7526
_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                   'Incoatec ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37982
_diffrn_reflns_av_unetI/netI     0.1011
_diffrn_reflns_av_R_equivalents  0.1239
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.387
_diffrn_reflns_theta_max         65.118
_diffrn_reflns_theta_full        65.118
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4780
_reflns_number_gt                3427
_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 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)+(0.0595P)²+0.8259P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4780
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.004
_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 0.94711(8) 0.67457(7) 0.69322(9) 0.0647(4) Uani 1 1 d . . . . .
Cl2 Cl 0.90879(8) 0.46922(7) 0.72852(8) 0.0578(3) Uani 1 1 d . . . . .
Cl3 Cl 0.18456(8) 0.21432(6) 0.56130(7) 0.0542(3) Uani 1 1 d . . . . .
Cl4 Cl -0.01382(8) 0.33443(6) 0.53186(7) 0.0518(3) Uani 1 1 d . . . . .
Cl5 Cl 0.11017(8) 0.99094(7) 0.40898(8) 0.0621(3) Uani 1 1 d . . . . .
Cl6 Cl 0.33589(8) 1.06680(5) 0.43410(7) 0.0472(3) Uani 1 1 d . . . . .
O1 O 0.35899(19) 0.67366(14) 0.85810(15) 0.0377(6) Uani 1 1 d . . . . .
N1 N 0.4865(2) 0.64741(17) 0.74608(18) 0.0322(7) Uani 1 1 d . . . . .
N2 N 0.4650(2) 0.48947(18) 0.72828(19) 0.0349(7) Uani 1 1 d . . . . .
N3 N 0.3213(2) 0.58650(17) 0.72081(19) 0.0318(7) Uani 1 1 d . . . . .
N4 N 0.1874(2) 0.67537(16) 0.64363(19) 0.0326(7) Uani 1 1 d . . . . .
N5 N 0.3469(2) 0.74155(17) 0.70073(19) 0.0316(6) Uani 1 1 d . . . . .
N6 N 0.5167(2) 0.79133(17) 0.68459(19) 0.0341(7) Uani 1 1 d . . . . .
C1 C 0.5510(3) 0.7117(2) 0.7175(2) 0.0349(8) Uani 1 1 d . . . . .
C2 C 0.6494(3) 0.6666(2) 0.7146(2) 0.0379(8) Uani 1 1 d . . . . .
C3 C 0.7455(3) 0.6975(2) 0.6984(3) 0.0417(9) Uani 1 1 d . . . . .
H3A H 0.755933 0.758609 0.683393 0.050 Uiso 1 1 calc R U . . .
C4 C 0.8258(3) 0.6367(3) 0.7049(3) 0.0433(9) Uani 1 1 d . . . . .
C5 C 0.8090(3) 0.5452(3) 0.7204(3) 0.0436(9) Uani 1 1 d . . . . .
C6 C 0.7124(3) 0.5134(2) 0.7304(2) 0.0404(9) Uani 1 1 d . . . . .
H6A H 0.700859 0.450994 0.737831 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6326(3) 0.5741(2) 0.7293(2) 0.0342(8) Uani 1 1 d . . . . .
C8 C 0.5250(3) 0.5626(2) 0.7410(2) 0.0326(8) Uani 1 1 d . . . . .
C9 C 0.3640(3) 0.5038(2) 0.7128(2) 0.0318(8) Uani 1 1 d . . . . .
C10 C 0.2816(3) 0.4487(2) 0.6679(2) 0.0333(8) Uani 1 1 d . . . . .
C11 C 0.2792(3) 0.3589(2) 0.6406(2) 0.0376(8) Uani 1 1 d . . . . .
H11A H 0.338274 0.322059 0.651854 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1886(3) 0.3251(2) 0.5969(2) 0.0380(9) Uani 1 1 d . . . . .
C13 C 0.1015(3) 0.3790(2) 0.5801(2) 0.0376(9) Uani 1 1 d . . . . .
C14 C 0.1050(3) 0.4699(2) 0.6014(2) 0.0361(8) Uani 1 1 d . . . . .
H14A H 0.046960 0.507231 0.585925 0.043 Uiso 1 1 calc R U . . .
C15 C 0.1952(3) 0.5044(2) 0.6457(2) 0.0331(8) Uani 1 1 d . . . . .
C16 C 0.2258(3) 0.5956(2) 0.6734(2) 0.0339(8) Uani 1 1 d . . . . .
C17 C 0.2517(3) 0.7460(2) 0.6522(2) 0.0320(8) Uani 1 1 d . . . . .
C18 C 0.2510(3) 0.82743(19) 0.5976(2) 0.0324(8) Uani 1 1 d . . . . .
C19 C 0.1760(3) 0.8677(2) 0.5362(2) 0.0384(9) Uani 1 1 d . . . . .
H19A H 0.108018 0.844799 0.528170 0.046 Uiso 1 1 calc R U . . .
C20 C 0.2026(3) 0.9420(2) 0.4871(2) 0.0400(9) Uani 1 1 d . . . . .
C21 C 0.3023(3) 0.9755(2) 0.4989(2) 0.0374(8) Uani 1 1 d . . . . .
C22 C 0.3787(3) 0.9369(2) 0.5588(2) 0.0348(8) Uani 1 1 d . . . . .
H22A H 0.446480 0.960061 0.565524 0.042 Uiso 1 1 calc R U . . .
C23 C 0.3524(3) 0.8623(2) 0.6091(2) 0.0318(8) Uani 1 1 d . . . . .
C24 C 0.4142(3) 0.8027(2) 0.6712(2) 0.0323(8) Uani 1 1 d . . . . .
C25 C 0.3796(3) 0.7524(2) 0.9050(2) 0.0377(8) Uani 1 1 d . . . . .
C26 C 0.2989(3) 0.8113(3) 0.9132(3) 0.0486(10) Uani 1 1 d . . . . .
H26A H 0.232020 0.798042 0.884494 0.058 Uiso 1 1 calc R U . . .
C27 C 0.3168(4) 0.8886(3) 0.9632(3) 0.0642(13) Uani 1 1 d . . . . .
H27A H 0.261697 0.928471 0.969732 0.077 Uiso 1 1 calc R U . . .
C28 C 0.4125(5) 0.9091(3) 1.0035(3) 0.0708(15) Uani 1 1 d . . . . .
H28A H 0.423522 0.963453 1.037194 0.085 Uiso 1 1 calc R U . . .
C29 C 0.4936(4) 0.8518(3) 0.9961(3) 0.0615(13) Uani 1 1 d . . . . .
H29A H 0.560272 0.866665 1.024267 0.074 Uiso 1 1 calc R U . . .
C30 C 0.4767(3) 0.7712(3) 0.9463(3) 0.0460(10) Uani 1 1 d . . . . .
H30A H 0.531503 0.730540 0.941323 0.055 Uiso 1 1 calc R U . . .
B1 B 0.3788(3) 0.6653(2) 0.7637(3) 0.0339(9) 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 C4 1.716(4) . ?
Cl2 C5 1.725(4) . ?
Cl3 C12 1.730(3) . ?
Cl4 C13 1.729(4) . ?
Cl5 C20 1.729(4) . ?
Cl6 C21 1.741(3) . ?
O1 C25 1.369(4) . ?
O1 B1 1.435(5) . ?
N1 C8 1.366(4) . ?
N1 C1 1.374(4) . ?
N1 B1 1.490(5) . ?
N2 C9 1.338(4) . ?
N2 C8 1.345(4) . ?
N3 C9 1.364(4) . ?
N3 C16 1.368(4) . ?
N3 B1 1.494(5) . ?
N4 C16 1.344(4) . ?
N4 C17 1.346(4) . ?
N5 C17 1.367(4) . ?
N5 C24 1.372(4) . ?
N5 B1 1.491(5) . ?
N6 C1 1.339(4) . ?
N6 C24 1.348(4) . ?
C1 C2 1.460(5) . ?
C2 C3 1.389(5) . ?
C2 C7 1.416(5) . ?
C3 C4 1.385(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.404(5) . ?
C5 C6 1.378(5) . ?
C6 C7 1.384(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.452(5) . ?
C9 C10 1.454(5) . ?
C10 C11 1.396(5) . ?
C10 C15 1.414(5) . ?
C11 C12 1.380(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.396(5) . ?
C13 C14 1.388(5) . ?
C14 C15 1.383(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.460(4) . ?
C17 C18 1.451(5) . ?
C18 C19 1.389(5) . ?
C18 C23 1.422(5) . ?
C19 C20 1.386(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.393(5) . ?
C21 C22 1.379(5) . ?
C22 C23 1.396(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.450(5) . ?
C25 C30 1.377(5) . ?
C25 C26 1.392(5) . ?
C26 C27 1.368(6) . ?
C26 H26A 0.9500 . ?
C27 C28 1.360(7) . ?
C27 H27A 0.9500 . ?
C28 C29 1.379(7) . ?
C28 H28A 0.9500 . ?
C29 C30 1.408(6) . ?
C29 H29A 0.9500 . ?
C30 H30A 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
C25 O1 B1 120.4(3) . . ?
C8 N1 C1 112.5(3) . . ?
C8 N1 B1 122.6(3) . . ?
C1 N1 B1 123.9(3) . . ?
C9 N2 C8 116.6(3) . . ?
C9 N3 C16 114.1(3) . . ?
C9 N3 B1 123.5(3) . . ?
C16 N3 B1 121.7(3) . . ?
C16 N4 C17 116.9(3) . . ?
C17 N5 C24 113.0(3) . . ?
C17 N5 B1 122.2(3) . . ?
C24 N5 B1 123.6(3) . . ?
C1 N6 C24 117.0(3) . . ?
N6 C1 N1 122.1(3) . . ?
N6 C1 C2 131.3(3) . . ?
N1 C1 C2 105.4(3) . . ?
C3 C2 C7 120.5(3) . . ?
C3 C2 C1 132.6(3) . . ?
C7 C2 C1 106.9(3) . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 Cl1 119.1(3) . . ?
C5 C4 Cl1 120.0(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 Cl2 117.9(3) . . ?
C4 C5 Cl2 121.1(3) . . ?
C5 C6 C7 118.6(3) . . ?
C5 C6 H6A 120.7 . . ?
C7 C6 H6A 120.7 . . ?
C6 C7 C2 120.5(3) . . ?
C6 C7 C8 131.8(3) . . ?
C2 C7 C8 107.6(3) . . ?
N2 C8 N1 122.8(3) . . ?
N2 C8 C7 129.9(3) . . ?
N1 C8 C7 105.6(3) . . ?
N2 C9 N3 122.7(3) . . ?
N2 C9 C10 131.3(3) . . ?
N3 C9 C10 104.8(3) . . ?
C11 C10 C15 120.4(3) . . ?
C11 C10 C9 131.4(3) . . ?
C15 C10 C9 108.0(3) . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 H11A 120.9 . . ?
C10 C11 H11A 120.9 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 Cl3 118.8(3) . . ?
C13 C12 Cl3 120.0(3) . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 Cl4 118.1(3) . . ?
C12 C13 Cl4 120.8(3) . . ?
C15 C14 C13 118.2(3) . . ?
C15 C14 H14A 120.9 . . ?
C13 C14 H14A 120.9 . . ?
C14 C15 C10 120.7(3) . . ?
C14 C15 C16 132.1(3) . . ?
C10 C15 C16 107.1(3) . . ?
N4 C16 N3 122.6(3) . . ?
N4 C16 C15 130.7(3) . . ?
N3 C16 C15 104.8(3) . . ?
N4 C17 N5 122.5(3) . . ?
N4 C17 C18 129.6(3) . . ?
N5 C17 C18 105.8(3) . . ?
C19 C18 C23 120.3(3) . . ?
C19 C18 C17 132.4(3) . . ?
C23 C18 C17 107.0(3) . . ?
C20 C19 C18 118.4(3) . . ?
C20 C19 H19A 120.8 . . ?
C18 C19 H19A 120.8 . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 Cl5 118.5(3) . . ?
C21 C20 Cl5 120.7(3) . . ?
C22 C21 C20 122.3(3) . . ?
C22 C21 Cl6 117.3(3) . . ?
C20 C21 Cl6 120.3(3) . . ?
C21 C22 C23 117.4(3) . . ?
C21 C22 H22A 121.3 . . ?
C23 C22 H22A 121.3 . . ?
C22 C23 C18 120.8(3) . . ?
C22 C23 C24 131.4(3) . . ?
C18 C23 C24 107.5(3) . . ?
N6 C24 N5 122.7(3) . . ?
N6 C24 C23 130.2(3) . . ?
N5 C24 C23 105.5(3) . . ?
O1 C25 C30 121.0(3) . . ?
O1 C25 C26 118.3(3) . . ?
C30 C25 C26 120.7(4) . . ?
C27 C26 C25 119.4(4) . . ?
C27 C26 H26A 120.3 . . ?
C25 C26 H26A 120.3 . . ?
C28 C27 C26 120.9(5) . . ?
C28 C27 H27A 119.5 . . ?
C26 C27 H27A 119.5 . . ?
C27 C28 C29 120.7(4) . . ?
C27 C28 H28A 119.6 . . ?
C29 C28 H28A 119.6 . . ?
C28 C29 C30 119.4(4) . . ?
C28 C29 H29A 120.3 . . ?
C30 C29 H29A 120.3 . . ?
C25 C30 C29 118.9(4) . . ?
C25 C30 H30A 120.5 . . ?
C29 C30 H30A 120.5 . . ?
O1 B1 N1 117.4(3) . . ?
O1 B1 N5 117.1(3) . . ?
N1 B1 N5 103.7(3) . . ?
O1 B1 N3 109.3(3) . . ?
N1 B1 N3 103.5(3) . . ?
N5 B1 N3 104.3(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
C24 N6 C1 N1 -6.9(5) . . . . ?
C24 N6 C1 C2 159.1(3) . . . . ?
C8 N1 C1 N6 154.9(3) . . . . ?
B1 N1 C1 N6 -14.3(5) . . . . ?
C8 N1 C1 C2 -14.3(4) . . . . ?
B1 N1 C1 C2 176.6(3) . . . . ?
N6 C1 C2 C3 18.4(6) . . . . ?
N1 C1 C2 C3 -173.9(4) . . . . ?
N6 C1 C2 C7 -159.6(3) . . . . ?
N1 C1 C2 C7 8.2(4) . . . . ?
C7 C2 C3 C4 -5.3(5) . . . . ?
C1 C2 C3 C4 177.0(4) . . . . ?
C2 C3 C4 C5 4.7(6) . . . . ?
C2 C3 C4 Cl1 -175.5(3) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
Cl1 C4 C5 C6 179.7(3) . . . . ?
C3 C4 C5 Cl2 -180.0(3) . . . . ?
Cl1 C4 C5 Cl2 0.2(5) . . . . ?
C4 C5 C6 C7 -3.1(5) . . . . ?
Cl2 C5 C6 C7 176.4(3) . . . . ?
C5 C6 C7 C2 2.4(5) . . . . ?
C5 C6 C7 C8 -177.6(4) . . . . ?
C3 C2 C7 C6 1.8(5) . . . . ?
C1 C2 C7 C6 -180.0(3) . . . . ?
C3 C2 C7 C8 -178.1(3) . . . . ?
C1 C2 C7 C8 0.1(4) . . . . ?
C9 N2 C8 N1 5.6(5) . . . . ?
C9 N2 C8 C7 -157.5(3) . . . . ?
C1 N1 C8 N2 -152.2(3) . . . . ?
B1 N1 C8 N2 17.0(5) . . . . ?
C1 N1 C8 C7 14.3(4) . . . . ?
B1 N1 C8 C7 -176.4(3) . . . . ?
C6 C7 C8 N2 -23.0(6) . . . . ?
C2 C7 C8 N2 156.9(3) . . . . ?
C6 C7 C8 N1 171.7(4) . . . . ?
C2 C7 C8 N1 -8.4(4) . . . . ?
C8 N2 C9 N3 -8.2(5) . . . . ?
C8 N2 C9 C10 157.0(3) . . . . ?
C16 N3 C9 N2 158.6(3) . . . . ?
B1 N3 C9 N2 -11.6(5) . . . . ?
C16 N3 C9 C10 -10.0(4) . . . . ?
B1 N3 C9 C10 179.9(3) . . . . ?
N2 C9 C10 C11 12.0(6) . . . . ?
N3 C9 C10 C11 179.1(4) . . . . ?
N2 C9 C10 C15 -163.0(3) . . . . ?
N3 C9 C10 C15 4.1(4) . . . . ?
C15 C10 C11 C12 -4.0(5) . . . . ?
C9 C10 C11 C12 -178.5(3) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C10 C11 C12 Cl3 179.2(3) . . . . ?
C11 C12 C13 C14 4.3(6) . . . . ?
Cl3 C12 C13 C14 -174.9(3) . . . . ?
C11 C12 C13 Cl4 -175.9(3) . . . . ?
Cl3 C12 C13 Cl4 5.0(4) . . . . ?
C12 C13 C14 C15 -4.5(5) . . . . ?
Cl4 C13 C14 C15 175.7(3) . . . . ?
C13 C14 C15 C10 0.5(5) . . . . ?
C13 C14 C15 C16 176.6(4) . . . . ?
C11 C10 C15 C14 3.8(5) . . . . ?
C9 C10 C15 C14 179.5(3) . . . . ?
C11 C10 C15 C16 -173.2(3) . . . . ?
C9 C10 C15 C16 2.5(4) . . . . ?
C17 N4 C16 N3 8.0(5) . . . . ?
C17 N4 C16 C15 -154.0(3) . . . . ?
C9 N3 C16 N4 -154.5(3) . . . . ?
B1 N3 C16 N4 15.8(5) . . . . ?
C9 N3 C16 C15 11.5(4) . . . . ?
B1 N3 C16 C15 -178.2(3) . . . . ?
C14 C15 C16 N4 -20.2(6) . . . . ?
C10 C15 C16 N4 156.3(3) . . . . ?
C14 C15 C16 N3 175.4(3) . . . . ?
C10 C15 C16 N3 -8.1(4) . . . . ?
C16 N4 C17 N5 -9.5(5) . . . . ?
C16 N4 C17 C18 152.1(3) . . . . ?
C24 N5 C17 N4 154.4(3) . . . . ?
B1 N5 C17 N4 -12.9(5) . . . . ?
C24 N5 C17 C18 -11.0(4) . . . . ?
B1 N5 C17 C18 -178.3(3) . . . . ?
N4 C17 C18 C19 16.9(6) . . . . ?
N5 C17 C18 C19 -179.1(4) . . . . ?
N4 C17 C18 C23 -157.3(3) . . . . ?
N5 C17 C18 C23 6.7(3) . . . . ?
C23 C18 C19 C20 0.0(5) . . . . ?
C17 C18 C19 C20 -173.5(3) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C18 C19 C20 Cl5 178.7(3) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
Cl5 C20 C21 C22 -178.3(3) . . . . ?
C19 C20 C21 Cl6 178.0(3) . . . . ?
Cl5 C20 C21 Cl6 -0.6(4) . . . . ?
C20 C21 C22 C23 -0.7(5) . . . . ?
Cl6 C21 C22 C23 -178.5(2) . . . . ?
C21 C22 C23 C18 0.8(5) . . . . ?
C21 C22 C23 C24 174.6(3) . . . . ?
C19 C18 C23 C22 -0.5(5) . . . . ?
C17 C18 C23 C22 174.5(3) . . . . ?
C19 C18 C23 C24 -175.6(3) . . . . ?
C17 C18 C23 C24 -0.5(4) . . . . ?
C1 N6 C24 N5 8.5(5) . . . . ?
C1 N6 C24 C23 -154.9(3) . . . . ?
C17 N5 C24 N6 -156.3(3) . . . . ?
B1 N5 C24 N6 10.8(5) . . . . ?
C17 N5 C24 C23 10.7(4) . . . . ?
B1 N5 C24 C23 177.8(3) . . . . ?
C22 C23 C24 N6 -14.6(6) . . . . ?
C18 C23 C24 N6 159.8(3) . . . . ?
C22 C23 C24 N5 179.9(3) . . . . ?
C18 C23 C24 N5 -5.8(3) . . . . ?
B1 O1 C25 C30 -83.6(4) . . . . ?
B1 O1 C25 C26 99.1(4) . . . . ?
O1 C25 C26 C27 177.2(3) . . . . ?
C30 C25 C26 C27 -0.1(5) . . . . ?
C25 C26 C27 C28 1.0(6) . . . . ?
C26 C27 C28 C29 -0.8(7) . . . . ?
C27 C28 C29 C30 -0.2(6) . . . . ?
O1 C25 C30 C29 -178.1(3) . . . . ?
C26 C25 C30 C29 -0.9(5) . . . . ?
C28 C29 C30 C25 1.0(6) . . . . ?
C25 O1 B1 N1 80.1(4) . . . . ?
C25 O1 B1 N5 -44.2(5) . . . . ?
C25 O1 B1 N3 -162.5(3) . . . . ?
C8 N1 B1 O1 89.5(4) . . . . ?
C1 N1 B1 O1 -102.4(4) . . . . ?
C8 N1 B1 N5 -139.7(3) . . . . ?
C1 N1 B1 N5 28.4(4) . . . . ?
C8 N1 B1 N3 -31.0(4) . . . . ?
C1 N1 B1 N3 137.1(3) . . . . ?
C17 N5 B1 O1 -89.6(4) . . . . ?
C24 N5 B1 O1 104.4(4) . . . . ?
C17 N5 B1 N1 139.4(3) . . . . ?
C24 N5 B1 N1 -26.6(4) . . . . ?
C17 N5 B1 N3 31.3(4) . . . . ?
C24 N5 B1 N3 -134.6(3) . . . . ?
C9 N3 B1 O1 -97.3(4) . . . . ?
C16 N3 B1 O1 93.3(4) . . . . ?
C9 N3 B1 N1 28.6(4) . . . . ?
C16 N3 B1 N1 -140.9(3) . . . . ?
C9 N3 B1 N5 136.8(3) . . . . ?
C16 N3 B1 N5 -32.7(4) . . . . ?

_refine_diff_density_max         0.679
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.110



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichlorobenzene/pentane'
####################################################################### 
# 
# 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_d19196_a
_database_code_depnum_ccdc_archive 'CCDC 2087097'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Cl-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 B Cl7 N6'
_chemical_formula_sum            'C24 H6 B Cl7 N6'
_chemical_formula_weight         637.31

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0807(7)
_cell_length_b                   7.4178(3)
_cell_length_c                   25.4738(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.502(2)
_cell_angle_gamma                90
_cell_volume                     2437.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.70

_exptl_crystal_description       Block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.845
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7196
_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                   'selaed 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            33605
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.621
_diffrn_reflns_theta_max         27.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5672
_reflns_number_gt                4980
_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 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)+(0.0320P)²+1.5824P] 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         5672
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Cl1 Cl 0.61269(3) -0.25222(5) 0.33889(2) 0.02260(8) Uani 1 1 d . . . . .
Cl2 Cl 0.35684(3) 0.78053(7) 0.40923(2) 0.04382(13) Uani 1 1 d . . . . .
Cl3 Cl 0.56244(3) 0.78107(6) 0.49200(2) 0.02872(9) Uani 1 1 d . . . . .
Cl4 Cl 1.20619(3) 0.27820(7) 0.40994(2) 0.03246(10) Uani 1 1 d . . . . .
Cl5 Cl 1.20990(3) 0.16565(7) 0.29148(2) 0.03609(11) Uani 1 1 d . . . . .
Cl6 Cl 0.60111(3) 0.18433(7) 0.02420(2) 0.03513(11) Uani 1 1 d . . . . .
Cl7 Cl 0.37788(3) 0.29251(6) 0.04365(2) 0.02959(10) Uani 1 1 d . . . . .
N1 N 0.60293(9) 0.12122(17) 0.34802(4) 0.0165(2) Uani 1 1 d . . . . .
N2 N 0.76204(9) 0.18413(17) 0.40514(5) 0.0180(2) Uani 1 1 d . . . . .
N3 N 0.75987(9) 0.01012(16) 0.32667(4) 0.0157(2) Uani 1 1 d . . . . .
N4 N 0.77375(9) -0.02875(16) 0.23543(5) 0.0161(2) Uani 1 1 d . . . . .
N5 N 0.60871(9) 0.01375(16) 0.26164(5) 0.0158(2) Uani 1 1 d . . . . .
N6 N 0.46582(9) 0.19132(17) 0.27729(5) 0.0177(2) Uani 1 1 d . . . . .
C1 C 0.51287(11) 0.2089(2) 0.32816(6) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.50032(11) 0.3458(2) 0.36780(6) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.42599(11) 0.4785(2) 0.36931(6) 0.0214(3) Uani 1 1 d . . . . .
H3A H 0.363996 0.480419 0.343936 0.026 Uiso 1 1 calc R U . . .
C4 C 0.44496(11) 0.6078(2) 0.40890(6) 0.0234(3) Uani 1 1 d . . . . .
C5 C 0.53663(12) 0.6074(2) 0.44661(6) 0.0215(3) Uani 1 1 d . . . . .
C6 C 0.61028(11) 0.4744(2) 0.44618(6) 0.0195(3) Uani 1 1 d . . . . .
H6A H 0.671614 0.472496 0.472007 0.023 Uiso 1 1 calc R U . . .
C7 C 0.59182(11) 0.3433(2) 0.40670(5) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.65915(11) 0.2043(2) 0.39122(5) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.81124(11) 0.09678(19) 0.37050(5) 0.0168(3) Uani 1 1 d . . . . .
C10 C 0.91795(11) 0.11204(19) 0.36181(5) 0.0171(3) Uani 1 1 d . . . . .
C11 C 1.00550(11) 0.1847(2) 0.39295(6) 0.0198(3) Uani 1 1 d . . . . .
H11A H 1.003763 0.224846 0.428200 0.024 Uiso 1 1 calc R U . . .
C12 C 1.09521(11) 0.1967(2) 0.37108(6) 0.0212(3) Uani 1 1 d . . . . .
C13 C 1.09729(11) 0.1438(2) 0.31817(6) 0.0213(3) Uani 1 1 d . . . . .
C14 C 1.01018(11) 0.0729(2) 0.28654(6) 0.0187(3) Uani 1 1 d . . . . .
H14A H 1.011333 0.039280 0.250661 0.022 Uiso 1 1 calc R U . . .
C15 C 0.92103(11) 0.05271(19) 0.30908(5) 0.0167(3) Uani 1 1 d . . . . .
C16 C 0.81710(11) -0.00507(19) 0.28653(5) 0.0159(3) Uani 1 1 d . . . . .
C17 C 0.67072(11) -0.00487(19) 0.22392(5) 0.0160(3) Uani 1 1 d . . . . .
C18 C 0.60843(11) 0.05263(19) 0.17469(5) 0.0167(3) Uani 1 1 d . . . . .
C19 C 0.63572(11) 0.0731(2) 0.12462(5) 0.0184(3) Uani 1 1 d . . . . .
H19A H 0.701618 0.035370 0.117704 0.022 Uiso 1 1 calc R U . . .
C20 C 0.56400(11) 0.1500(2) 0.08531(6) 0.0204(3) Uani 1 1 d . . . . .
C21 C 0.46546(11) 0.2034(2) 0.09522(6) 0.0203(3) Uani 1 1 d . . . . .
C22 C 0.43916(11) 0.1889(2) 0.14556(6) 0.0194(3) Uani 1 1 d . . . . .
H22A H 0.373356 0.227999 0.152253 0.023 Uiso 1 1 calc R U . . .
C23 C 0.51189(11) 0.11548(19) 0.18616(5) 0.0171(3) Uani 1 1 d . . . . .
C24 C 0.51802(11) 0.10223(19) 0.24394(5) 0.0169(3) Uani 1 1 d . . . . .
B1 B 0.64642(12) -0.0244(2) 0.31877(6) 0.0161(3) 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 1.8403(16) . ?
Cl2 C4 1.7242(16) . ?
Cl3 C5 1.7268(15) . ?
Cl4 C12 1.7259(15) . ?
Cl5 C13 1.7288(15) . ?
Cl6 C20 1.7244(15) . ?
Cl7 C21 1.7259(15) . ?
N1 C8 1.3654(18) . ?
N1 C1 1.3674(18) . ?
N1 B1 1.479(2) . ?
N2 C9 1.3416(18) . ?
N2 C8 1.3423(19) . ?
N3 C9 1.3652(18) . ?
N3 C16 1.3679(17) . ?
N3 B1 1.4866(19) . ?
N4 C16 1.3429(18) . ?
N4 C17 1.3428(18) . ?
N5 C17 1.3630(17) . ?
N5 C24 1.3655(18) . ?
N5 B1 1.4849(19) . ?
N6 C1 1.3460(18) . ?
N6 C24 1.3477(18) . ?
C1 C2 1.460(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.422(2) . ?
C3 C4 1.385(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.407(2) . ?
C5 C6 1.380(2) . ?
C6 C7 1.391(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.453(2) . ?
C9 C10 1.4535(19) . ?
C10 C11 1.390(2) . ?
C10 C15 1.4202(19) . ?
C11 C12 1.382(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.408(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.3904(19) . ?
C14 H14A 0.9500 . ?
C15 C16 1.4505(19) . ?
C17 C18 1.4426(19) . ?
C18 C19 1.3883(19) . ?
C18 C23 1.4210(19) . ?
C19 C20 1.378(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.410(2) . ?
C21 C22 1.386(2) . ?
C22 C23 1.395(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.4642(19) . ?

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
C8 N1 C1 113.58(12) . . ?
C8 N1 B1 122.34(12) . . ?
C1 N1 B1 122.74(12) . . ?
C9 N2 C8 116.68(12) . . ?
C9 N3 C16 113.20(12) . . ?
C9 N3 B1 122.51(12) . . ?
C16 N3 B1 122.82(12) . . ?
C16 N4 C17 116.25(12) . . ?
C17 N5 C24 113.68(12) . . ?
C17 N5 B1 122.11(12) . . ?
C24 N5 B1 123.04(12) . . ?
C1 N6 C24 117.10(12) . . ?
N6 C1 N1 122.62(13) . . ?
N6 C1 C2 130.35(13) . . ?
N1 C1 C2 105.26(12) . . ?
C3 C2 C7 120.15(14) . . ?
C3 C2 C1 132.15(14) . . ?
C7 C2 C1 107.18(12) . . ?
C4 C3 C2 117.99(14) . . ?
C4 C3 H3A 121.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 C5 121.71(14) . . ?
C3 C4 Cl2 118.61(12) . . ?
C5 C4 Cl2 119.57(12) . . ?
C6 C5 C4 120.90(14) . . ?
C6 C5 Cl3 118.62(12) . . ?
C4 C5 Cl3 120.38(12) . . ?
C5 C6 C7 117.86(14) . . ?
C5 C6 H6A 121.1 . . ?
C7 C6 H6A 121.1 . . ?
C6 C7 C2 121.37(14) . . ?
C6 C7 C8 130.70(14) . . ?
C2 C7 C8 107.33(12) . . ?
N2 C8 N1 123.08(13) . . ?
N2 C8 C7 129.33(13) . . ?
N1 C8 C7 105.62(12) . . ?
N2 C9 N3 122.72(13) . . ?
N2 C9 C10 129.77(13) . . ?
N3 C9 C10 105.51(12) . . ?
C11 C10 C15 120.71(13) . . ?
C11 C10 C9 131.68(13) . . ?
C15 C10 C9 107.33(12) . . ?
C12 C11 C10 117.99(13) . . ?
C12 C11 H11A 121.0 . . ?
C10 C11 H11A 121.0 . . ?
C11 C12 C13 121.30(13) . . ?
C11 C12 Cl4 118.75(11) . . ?
C13 C12 Cl4 119.95(11) . . ?
C14 C13 C12 121.20(13) . . ?
C14 C13 Cl5 118.63(11) . . ?
C12 C13 Cl5 120.17(12) . . ?
C13 C14 C15 117.78(13) . . ?
C13 C14 H14A 121.1 . . ?
C15 C14 H14A 121.1 . . ?
C14 C15 C10 120.92(13) . . ?
C14 C15 C16 131.56(13) . . ?
C10 C15 C16 107.16(12) . . ?
N4 C16 N3 122.67(12) . . ?
N4 C16 C15 129.85(12) . . ?
N3 C16 C15 105.81(12) . . ?
N4 C17 N5 123.51(12) . . ?
N4 C17 C18 129.15(12) . . ?
N5 C17 C18 105.45(12) . . ?
C19 C18 C23 121.67(13) . . ?
C19 C18 C17 129.56(13) . . ?
C23 C18 C17 108.17(12) . . ?
C20 C19 C18 117.74(13) . . ?
C20 C19 H19A 121.1 . . ?
C18 C19 H19A 121.1 . . ?
C19 C20 C21 121.27(13) . . ?
C19 C20 Cl6 117.24(11) . . ?
C21 C20 Cl6 121.46(11) . . ?
C22 C21 C20 121.18(13) . . ?
C22 C21 Cl7 119.94(12) . . ?
C20 C21 Cl7 118.87(11) . . ?
C21 C22 C23 118.24(13) . . ?
C21 C22 H22A 120.9 . . ?
C23 C22 H22A 120.9 . . ?
C22 C23 C18 119.74(13) . . ?
C22 C23 C24 133.55(13) . . ?
C18 C23 C24 106.36(12) . . ?
N6 C24 N5 122.04(12) . . ?
N6 C24 C23 130.65(13) . . ?
N5 C24 C23 105.34(12) . . ?
N1 B1 N5 105.14(12) . . ?
N1 B1 N3 105.33(12) . . ?
N5 B1 N3 105.21(11) . . ?
N1 B1 Cl1 113.63(10) . . ?
N5 B1 Cl1 113.08(10) . . ?
N3 B1 Cl1 113.61(11) . . ?

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 -8.8(2) . . . . ?
C24 N6 C1 C2 153.75(14) . . . . ?
C8 N1 C1 N6 155.77(13) . . . . ?
B1 N1 C1 N6 -11.3(2) . . . . ?
C8 N1 C1 C2 -10.52(15) . . . . ?
B1 N1 C1 C2 -177.60(12) . . . . ?
N6 C1 C2 C3 13.1(3) . . . . ?
N1 C1 C2 C3 177.91(15) . . . . ?
N6 C1 C2 C7 -158.35(14) . . . . ?
N1 C1 C2 C7 6.47(15) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 -169.46(15) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C2 C3 C4 Cl2 176.55(11) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
Cl2 C4 C5 C6 -177.72(11) . . . . ?
C3 C4 C5 Cl3 174.68(12) . . . . ?
Cl2 C4 C5 Cl3 -1.49(18) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
Cl3 C5 C6 C7 -175.07(11) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
C5 C6 C7 C8 170.12(14) . . . . ?
C3 C2 C7 C6 -1.4(2) . . . . ?
C1 C2 C7 C6 171.29(13) . . . . ?
C3 C2 C7 C8 -173.39(13) . . . . ?
C1 C2 C7 C8 -0.72(15) . . . . ?
C9 N2 C8 N1 8.8(2) . . . . ?
C9 N2 C8 C7 -152.87(14) . . . . ?
C1 N1 C8 N2 -155.23(13) . . . . ?
B1 N1 C8 N2 11.9(2) . . . . ?
C1 N1 C8 C7 10.11(15) . . . . ?
B1 N1 C8 C7 177.24(12) . . . . ?
C6 C7 C8 N2 -12.2(3) . . . . ?
C2 C7 C8 N2 158.77(14) . . . . ?
C6 C7 C8 N1 -176.31(14) . . . . ?
C2 C7 C8 N1 -5.32(15) . . . . ?
C8 N2 C9 N3 -8.8(2) . . . . ?
C8 N2 C9 C10 152.67(14) . . . . ?
C16 N3 C9 N2 154.77(13) . . . . ?
B1 N3 C9 N2 -11.7(2) . . . . ?
C16 N3 C9 C10 -10.54(16) . . . . ?
B1 N3 C9 C10 -177.02(12) . . . . ?
N2 C9 C10 C11 17.2(3) . . . . ?
N3 C9 C10 C11 -178.88(15) . . . . ?
N2 C9 C10 C15 -156.44(14) . . . . ?
N3 C9 C10 C15 7.45(15) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C9 C10 C11 C12 -173.15(15) . . . . ?
C10 C11 C12 C13 2.4(2) . . . . ?
C10 C11 C12 Cl4 -177.48(11) . . . . ?
C11 C12 C13 C14 -1.8(2) . . . . ?
Cl4 C12 C13 C14 178.10(12) . . . . ?
C11 C12 C13 Cl5 178.40(12) . . . . ?
Cl4 C12 C13 Cl5 -1.67(19) . . . . ?
C12 C13 C14 C15 -1.1(2) . . . . ?
Cl5 C13 C14 C15 178.63(12) . . . . ?
C13 C14 C15 C10 3.4(2) . . . . ?
C13 C14 C15 C16 175.57(15) . . . . ?
C11 C10 C15 C14 -2.8(2) . . . . ?
C9 C10 C15 C14 171.70(13) . . . . ?
C11 C10 C15 C16 -176.68(13) . . . . ?
C9 C10 C15 C16 -2.17(15) . . . . ?
C17 N4 C16 N3 11.5(2) . . . . ?
C17 N4 C16 C15 -151.53(15) . . . . ?
C9 N3 C16 N4 -157.31(13) . . . . ?
B1 N3 C16 N4 9.1(2) . . . . ?
C9 N3 C16 C15 9.23(16) . . . . ?
B1 N3 C16 C15 175.66(12) . . . . ?
C14 C15 C16 N4 -11.7(3) . . . . ?
C10 C15 C16 N4 161.30(14) . . . . ?
C14 C15 C16 N3 -176.88(15) . . . . ?
C10 C15 C16 N3 -3.91(15) . . . . ?
C16 N4 C17 N5 -10.3(2) . . . . ?
C16 N4 C17 C18 151.68(15) . . . . ?
C24 N5 C17 N4 156.38(13) . . . . ?
B1 N5 C17 N4 -11.6(2) . . . . ?
C24 N5 C17 C18 -9.21(16) . . . . ?
B1 N5 C17 C18 -177.22(12) . . . . ?
N4 C17 C18 C19 10.4(3) . . . . ?
N5 C17 C18 C19 174.87(15) . . . . ?
N4 C17 C18 C23 -160.70(14) . . . . ?
N5 C17 C18 C23 3.79(15) . . . . ?
C23 C18 C19 C20 -2.7(2) . . . . ?
C17 C18 C19 C20 -172.77(15) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C18 C19 C20 Cl6 177.04(11) . . . . ?
C19 C20 C21 C22 3.4(2) . . . . ?
Cl6 C20 C21 C22 -174.68(12) . . . . ?
C19 C20 C21 Cl7 -178.04(12) . . . . ?
Cl6 C20 C21 Cl7 3.91(19) . . . . ?
C20 C21 C22 C23 -1.7(2) . . . . ?
Cl7 C21 C22 C23 179.74(11) . . . . ?
C21 C22 C23 C18 -2.1(2) . . . . ?
C21 C22 C23 C24 170.01(15) . . . . ?
C19 C18 C23 C22 4.4(2) . . . . ?
C17 C18 C23 C22 176.32(13) . . . . ?
C19 C18 C23 C24 -169.63(13) . . . . ?
C17 C18 C23 C24 2.30(16) . . . . ?
C1 N6 C24 N5 8.0(2) . . . . ?
C1 N6 C24 C23 -153.60(15) . . . . ?
C17 N5 C24 N6 -154.98(13) . . . . ?
B1 N5 C24 N6 12.9(2) . . . . ?
C17 N5 C24 C23 10.63(16) . . . . ?
B1 N5 C24 C23 178.51(12) . . . . ?
C22 C23 C24 N6 -16.5(3) . . . . ?
C18 C23 C24 N6 156.38(14) . . . . ?
C22 C23 C24 N5 179.67(15) . . . . ?
C18 C23 C24 N5 -7.50(15) . . . . ?
C8 N1 B1 N5 -138.60(13) . . . . ?
C1 N1 B1 N5 27.35(17) . . . . ?
C8 N1 B1 N3 -27.75(17) . . . . ?
C1 N1 B1 N3 138.20(13) . . . . ?
C8 N1 B1 Cl1 97.23(14) . . . . ?
C1 N1 B1 Cl1 -96.82(14) . . . . ?
C17 N5 B1 N1 138.64(13) . . . . ?
C24 N5 B1 N1 -28.24(17) . . . . ?
C17 N5 B1 N3 27.70(18) . . . . ?
C24 N5 B1 N3 -139.18(13) . . . . ?
C17 N5 B1 Cl1 -96.84(14) . . . . ?
C24 N5 B1 Cl1 96.28(14) . . . . ?
C9 N3 B1 N1 27.74(17) . . . . ?
C16 N3 B1 N1 -137.45(13) . . . . ?
C9 N3 B1 N5 138.54(13) . . . . ?
C16 N3 B1 N5 -26.65(18) . . . . ?
C9 N3 B1 Cl1 -97.25(14) . . . . ?
C16 N3 B1 Cl1 97.56(14) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.052



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichlorobenzene/dimethoxybezene/heptane'
####################################################################### 
# 
# 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_d19152_a
_database_code_depnum_ccdc_archive 'CCDC 2087093'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        PhO-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H11 B Cl6 N6 O'
_chemical_formula_sum            'C30 H11 B Cl6 N6 O'
_chemical_formula_weight         694.96

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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                   13.1387(10)
_cell_length_b                   14.9262(10)
_cell_length_c                   14.6051(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.620(2)
_cell_angle_gamma                90
_cell_volume                     2845.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5554
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.69

_exptl_crystal_description       Block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.643
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7022
_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            35148
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.560
_diffrn_reflns_theta_max         27.591
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6539
_reflns_number_gt                4135
_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 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)+(0.0383P)²+1.4189P] 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         6539
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
Cl1 Cl 0.94752(5) 0.67466(6) 0.69356(7) 0.0502(2) Uani 1 1 d . . . . .
Cl2 Cl 0.90910(5) 0.46933(5) 0.72907(6) 0.0435(2) Uani 1 1 d . . . . .
Cl3 Cl 0.18493(6) 0.21468(4) 0.56129(5) 0.0401(2) Uani 1 1 d . . . . .
Cl4 Cl -0.01375(5) 0.33449(4) 0.53202(5) 0.03731(19) Uani 1 1 d . . . . .
Cl5 Cl 0.11008(6) 0.99051(5) 0.40911(6) 0.0493(2) Uani 1 1 d . . . . .
Cl6 Cl 0.33578(6) 1.06649(4) 0.43431(5) 0.03410(18) Uani 1 1 d . . . . .
O1 O 0.35913(13) 0.67372(11) 0.85794(12) 0.0248(4) Uani 1 1 d . . . . .
N1 N 0.48681(15) 0.64735(13) 0.74609(14) 0.0204(5) Uani 1 1 d . . . . .
N2 N 0.46546(15) 0.48981(13) 0.72857(14) 0.0215(5) Uani 1 1 d . . . . .
N3 N 0.32127(15) 0.58676(13) 0.72103(14) 0.0197(5) Uani 1 1 d . . . . .
N4 N 0.18754(15) 0.67533(13) 0.64379(14) 0.0218(5) Uani 1 1 d . . . . .
N5 N 0.34698(15) 0.74159(13) 0.70092(13) 0.0184(4) Uani 1 1 d . . . . .
N6 N 0.51690(15) 0.79110(13) 0.68440(14) 0.0209(5) Uani 1 1 d . . . . .
C1 C 0.55053(18) 0.71165(16) 0.71802(17) 0.0212(6) Uani 1 1 d . . . . .
C2 C 0.64890(18) 0.66696(17) 0.71429(17) 0.0226(6) Uani 1 1 d . . . . .
C3 C 0.74555(19) 0.69768(18) 0.69875(18) 0.0278(6) Uani 1 1 d . . . . .
H3A H 0.756290 0.758811 0.684502 0.033 Uiso 1 1 calc R U . . .
C4 C 0.82540(19) 0.63691(19) 0.70460(19) 0.0300(6) Uani 1 1 d . . . . .
C5 C 0.8088(2) 0.54509(19) 0.72064(19) 0.0293(6) Uani 1 1 d . . . . .
C6 C 0.71239(19) 0.51320(18) 0.73044(17) 0.0256(6) Uani 1 1 d . . . . .
H6A H 0.700729 0.450911 0.737631 0.031 Uiso 1 1 calc R U . . .
C7 C 0.63264(19) 0.57419(17) 0.72955(17) 0.0227(6) Uani 1 1 d . . . . .
C8 C 0.52516(19) 0.56281(16) 0.74093(17) 0.0215(5) Uani 1 1 d . . . . .
C9 C 0.36380(18) 0.50439(16) 0.71302(17) 0.0206(5) Uani 1 1 d . . . . .
C10 C 0.28202(19) 0.44865(16) 0.66820(17) 0.0215(6) Uani 1 1 d . . . . .
C11 C 0.27967(19) 0.35928(16) 0.64102(18) 0.0238(6) Uani 1 1 d . . . . .
H11A H 0.338740 0.322455 0.652488 0.029 Uiso 1 1 calc R U . . .
C12 C 0.1890(2) 0.32552(16) 0.59685(18) 0.0266(6) Uani 1 1 d . . . . .
C13 C 0.1012(2) 0.37953(17) 0.58022(18) 0.0256(6) Uani 1 1 d . . . . .
C14 C 0.10469(19) 0.46977(16) 0.60103(18) 0.0234(6) Uani 1 1 d . . . . .
H14A H 0.046720 0.507040 0.585166 0.028 Uiso 1 1 calc R U . . .
C15 C 0.19520(18) 0.50476(16) 0.64583(17) 0.0213(5) Uani 1 1 d . . . . .
C16 C 0.22609(18) 0.59579(16) 0.67362(17) 0.0201(5) Uani 1 1 d . . . . .
C17 C 0.25196(18) 0.74585(16) 0.65219(17) 0.0205(5) Uani 1 1 d . . . . .
C18 C 0.25117(19) 0.82752(15) 0.59773(17) 0.0212(5) Uani 1 1 d . . . . .
C19 C 0.1756(2) 0.86735(16) 0.53625(18) 0.0257(6) Uani 1 1 d . . . . .
H19A H 0.107825 0.844273 0.528005 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2024(2) 0.94155(17) 0.48755(19) 0.0276(6) Uani 1 1 d . . . . .
C21 C 0.3026(2) 0.97543(16) 0.49922(18) 0.0251(6) Uani 1 1 d . . . . .
C22 C 0.37830(19) 0.93605(16) 0.55910(17) 0.0223(6) Uani 1 1 d . . . . .
H22A H 0.446175 0.959046 0.566064 0.027 Uiso 1 1 calc R U . . .
C23 C 0.35268(19) 0.86190(16) 0.60892(17) 0.0208(5) Uani 1 1 d . . . . .
C24 C 0.41448(19) 0.80211(16) 0.67104(17) 0.0199(5) Uani 1 1 d . . . . .
C25 C 0.3799(2) 0.75234(17) 0.90507(17) 0.0242(6) Uani 1 1 d . . . . .
C26 C 0.2994(2) 0.81119(19) 0.91373(19) 0.0347(7) Uani 1 1 d . . . . .
H26A H 0.232471 0.797541 0.885434 0.042 Uiso 1 1 calc R U . . .
C27 C 0.3169(3) 0.8891(2) 0.9632(2) 0.0517(9) Uani 1 1 d . . . . .
H27A H 0.261787 0.929092 0.969063 0.062 Uiso 1 1 calc R U . . .
C28 C 0.4132(4) 0.9094(2) 1.0042(2) 0.0556(10) Uani 1 1 d . . . . .
H28A H 0.424715 0.963247 1.038403 0.067 Uiso 1 1 calc R U . . .
C29 C 0.4934(3) 0.8514(2) 0.9957(2) 0.0489(9) Uani 1 1 d . . . . .
H29A H 0.560250 0.866051 1.023481 0.059 Uiso 1 1 calc R U . . .
C30 C 0.4770(2) 0.77119(19) 0.94645(18) 0.0327(7) Uani 1 1 d . . . . .
H30A H 0.531853 0.730592 0.941703 0.039 Uiso 1 1 calc R U . . .
B1 B 0.3789(2) 0.66509(18) 0.7639(2) 0.0203(6) 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 C4 1.726(3) . ?
Cl2 C5 1.730(3) . ?
Cl3 C12 1.733(2) . ?
Cl4 C13 1.728(3) . ?
Cl5 C20 1.731(3) . ?
Cl6 C21 1.741(3) . ?
O1 C25 1.372(3) . ?
O1 B1 1.433(3) . ?
N1 C8 1.364(3) . ?
N1 C1 1.367(3) . ?
N1 B1 1.494(3) . ?
N2 C8 1.342(3) . ?
N2 C9 1.347(3) . ?
N3 C9 1.361(3) . ?
N3 C16 1.364(3) . ?
N3 B1 1.491(3) . ?
N4 C16 1.343(3) . ?
N4 C17 1.348(3) . ?
N5 C17 1.365(3) . ?
N5 C24 1.372(3) . ?
N5 B1 1.495(3) . ?
N6 C1 1.339(3) . ?
N6 C24 1.347(3) . ?
C1 C2 1.461(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.423(3) . ?
C3 C4 1.382(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.412(4) . ?
C5 C6 1.376(4) . ?
C6 C7 1.387(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.451(3) . ?
C9 C10 1.454(3) . ?
C10 C11 1.391(3) . ?
C10 C15 1.423(3) . ?
C11 C12 1.383(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.405(4) . ?
C13 C14 1.380(3) . ?
C14 C15 1.391(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.462(3) . ?
C17 C18 1.455(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.421(3) . ?
C19 C20 1.383(4) . ?
C19 H19A 0.9500 . ?
C20 C21 1.402(4) . ?
C21 C22 1.378(4) . ?
C22 C23 1.387(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.452(3) . ?
C25 C30 1.377(4) . ?
C25 C26 1.391(4) . ?
C26 C27 1.374(4) . ?
C26 H26A 0.9500 . ?
C27 C28 1.369(5) . ?
C27 H27A 0.9500 . ?
C28 C29 1.380(5) . ?
C28 H28A 0.9500 . ?
C29 C30 1.400(4) . ?
C29 H29A 0.9500 . ?
C30 H30A 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
C25 O1 B1 120.69(19) . . ?
C8 N1 C1 113.0(2) . . ?
C8 N1 B1 122.5(2) . . ?
C1 N1 B1 123.6(2) . . ?
C8 N2 C9 116.4(2) . . ?
C9 N3 C16 114.0(2) . . ?
C9 N3 B1 123.4(2) . . ?
C16 N3 B1 121.8(2) . . ?
C16 N4 C17 116.8(2) . . ?
C17 N5 C24 112.9(2) . . ?
C17 N5 B1 122.1(2) . . ?
C24 N5 B1 123.6(2) . . ?
C1 N6 C24 116.3(2) . . ?
N6 C1 N1 123.0(2) . . ?
N6 C1 C2 130.3(2) . . ?
N1 C1 C2 105.4(2) . . ?
C3 C2 C7 120.1(2) . . ?
C3 C2 C1 133.1(2) . . ?
C7 C2 C1 106.8(2) . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 Cl1 119.2(2) . . ?
C5 C4 Cl1 119.7(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 Cl2 118.0(2) . . ?
C4 C5 Cl2 121.0(2) . . ?
C5 C6 C7 118.4(2) . . ?
C5 C6 H6A 120.8 . . ?
C7 C6 H6A 120.8 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 C8 131.8(2) . . ?
C2 C7 C8 107.3(2) . . ?
N2 C8 N1 123.0(2) . . ?
N2 C8 C7 129.9(2) . . ?
N1 C8 C7 105.6(2) . . ?
N2 C9 N3 122.7(2) . . ?
N2 C9 C10 130.6(2) . . ?
N3 C9 C10 105.4(2) . . ?
C11 C10 C15 120.5(2) . . ?
C11 C10 C9 131.9(2) . . ?
C15 C10 C9 107.3(2) . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 H11A 120.9 . . ?
C10 C11 H11A 120.9 . . ?
C11 C12 C13 121.2(2) . . ?
C11 C12 Cl3 118.9(2) . . ?
C13 C12 Cl3 120.0(2) . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 Cl4 118.3(2) . . ?
C12 C13 Cl4 120.59(19) . . ?
C13 C14 C15 118.3(2) . . ?
C13 C14 H14A 120.8 . . ?
C15 C14 H14A 120.8 . . ?
C14 C15 C10 120.4(2) . . ?
C14 C15 C16 132.4(2) . . ?
C10 C15 C16 107.1(2) . . ?
N4 C16 N3 122.8(2) . . ?
N4 C16 C15 130.5(2) . . ?
N3 C16 C15 104.9(2) . . ?
N4 C17 N5 122.6(2) . . ?
N4 C17 C18 129.8(2) . . ?
N5 C17 C18 105.8(2) . . ?
C19 C18 C23 120.6(2) . . ?
C19 C18 C17 132.1(2) . . ?
C23 C18 C17 107.0(2) . . ?
C20 C19 C18 118.0(2) . . ?
C20 C19 H19A 121.0 . . ?
C18 C19 H19A 121.0 . . ?
C19 C20 C21 121.1(2) . . ?
C19 C20 Cl5 118.6(2) . . ?
C21 C20 Cl5 120.3(2) . . ?
C22 C21 C20 121.5(2) . . ?
C22 C21 Cl6 118.1(2) . . ?
C20 C21 Cl6 120.4(2) . . ?
C21 C22 C23 118.2(2) . . ?
C21 C22 H22A 120.9 . . ?
C23 C22 H22A 120.9 . . ?
C22 C23 C18 120.6(2) . . ?
C22 C23 C24 131.8(2) . . ?
C18 C23 C24 107.4(2) . . ?
N6 C24 N5 123.0(2) . . ?
N6 C24 C23 130.0(2) . . ?
N5 C24 C23 105.5(2) . . ?
O1 C25 C30 121.0(2) . . ?
O1 C25 C26 118.5(2) . . ?
C30 C25 C26 120.4(3) . . ?
C27 C26 C25 120.0(3) . . ?
C27 C26 H26A 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 H27A 119.8 . . ?
C26 C27 H27A 119.8 . . ?
C27 C28 C29 119.9(3) . . ?
C27 C28 H28A 120.0 . . ?
C29 C28 H28A 120.0 . . ?
C28 C29 C30 120.6(3) . . ?
C28 C29 H29A 119.7 . . ?
C30 C29 H29A 119.7 . . ?
C25 C30 C29 118.7(3) . . ?
C25 C30 H30A 120.7 . . ?
C29 C30 H30A 120.7 . . ?
O1 B1 N3 109.5(2) . . ?
O1 B1 N1 117.6(2) . . ?
N3 B1 N1 103.5(2) . . ?
O1 B1 N5 116.9(2) . . ?
N3 B1 N5 104.4(2) . . ?
N1 B1 N5 103.5(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
C24 N6 C1 N1 -6.1(3) . . . . ?
C24 N6 C1 C2 158.6(2) . . . . ?
C8 N1 C1 N6 154.2(2) . . . . ?
B1 N1 C1 N6 -15.2(4) . . . . ?
C8 N1 C1 C2 -13.8(3) . . . . ?
B1 N1 C1 C2 176.8(2) . . . . ?
N6 C1 C2 C3 19.8(5) . . . . ?
N1 C1 C2 C3 -173.4(3) . . . . ?
N6 C1 C2 C7 -159.4(2) . . . . ?
N1 C1 C2 C7 7.4(3) . . . . ?
C7 C2 C3 C4 -4.1(4) . . . . ?
C1 C2 C3 C4 176.7(3) . . . . ?
C2 C3 C4 C5 3.6(4) . . . . ?
C2 C3 C4 Cl1 -175.5(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
Cl1 C4 C5 C6 179.5(2) . . . . ?
C3 C4 C5 Cl2 -179.4(2) . . . . ?
Cl1 C4 C5 Cl2 -0.2(3) . . . . ?
C4 C5 C6 C7 -3.7(4) . . . . ?
Cl2 C5 C6 C7 176.0(2) . . . . ?
C5 C6 C7 C2 3.1(4) . . . . ?
C5 C6 C7 C8 -177.8(3) . . . . ?
C3 C2 C7 C6 0.8(4) . . . . ?
C1 C2 C7 C6 -179.8(2) . . . . ?
C3 C2 C7 C8 -178.5(2) . . . . ?
C1 C2 C7 C8 0.9(3) . . . . ?
C9 N2 C8 N1 5.8(3) . . . . ?
C9 N2 C8 C7 -157.8(2) . . . . ?
C1 N1 C8 N2 -152.6(2) . . . . ?
B1 N1 C8 N2 16.9(4) . . . . ?
C1 N1 C8 C7 14.4(3) . . . . ?
B1 N1 C8 C7 -176.1(2) . . . . ?
C6 C7 C8 N2 -22.3(5) . . . . ?
C2 C7 C8 N2 156.9(3) . . . . ?
C6 C7 C8 N1 171.9(3) . . . . ?
C2 C7 C8 N1 -8.8(3) . . . . ?
C8 N2 C9 N3 -8.4(3) . . . . ?
C8 N2 C9 C10 157.0(2) . . . . ?
C16 N3 C9 N2 158.5(2) . . . . ?
B1 N3 C9 N2 -11.6(4) . . . . ?
C16 N3 C9 C10 -10.1(3) . . . . ?
B1 N3 C9 C10 179.8(2) . . . . ?
N2 C9 C10 C11 11.8(5) . . . . ?
N3 C9 C10 C11 179.1(3) . . . . ?
N2 C9 C10 C15 -163.1(2) . . . . ?
N3 C9 C10 C15 4.1(3) . . . . ?
C15 C10 C11 C12 -3.8(4) . . . . ?
C9 C10 C11 C12 -178.2(3) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C10 C11 C12 Cl3 179.3(2) . . . . ?
C11 C12 C13 C14 5.0(4) . . . . ?
Cl3 C12 C13 C14 -174.7(2) . . . . ?
C11 C12 C13 Cl4 -175.6(2) . . . . ?
Cl3 C12 C13 Cl4 4.7(3) . . . . ?
C12 C13 C14 C15 -5.1(4) . . . . ?
Cl4 C13 C14 C15 175.5(2) . . . . ?
C13 C14 C15 C10 0.8(4) . . . . ?
C13 C14 C15 C16 176.8(3) . . . . ?
C11 C10 C15 C14 3.7(4) . . . . ?
C9 C10 C15 C14 179.3(2) . . . . ?
C11 C10 C15 C16 -173.2(2) . . . . ?
C9 C10 C15 C16 2.5(3) . . . . ?
C17 N4 C16 N3 8.3(4) . . . . ?
C17 N4 C16 C15 -153.9(3) . . . . ?
C9 N3 C16 N4 -154.5(2) . . . . ?
B1 N3 C16 N4 15.8(4) . . . . ?
C9 N3 C16 C15 11.5(3) . . . . ?
B1 N3 C16 C15 -178.2(2) . . . . ?
C14 C15 C16 N4 -19.9(5) . . . . ?
C10 C15 C16 N4 156.4(3) . . . . ?
C14 C15 C16 N3 175.5(3) . . . . ?
C10 C15 C16 N3 -8.1(3) . . . . ?
C16 N4 C17 N5 -9.9(4) . . . . ?
C16 N4 C17 C18 152.4(3) . . . . ?
C24 N5 C17 N4 154.1(2) . . . . ?
B1 N5 C17 N4 -12.5(4) . . . . ?
C24 N5 C17 C18 -11.8(3) . . . . ?
B1 N5 C17 C18 -178.4(2) . . . . ?
N4 C17 C18 C19 16.4(5) . . . . ?
N5 C17 C18 C19 -179.1(3) . . . . ?
N4 C17 C18 C23 -157.1(3) . . . . ?
N5 C17 C18 C23 7.4(3) . . . . ?
C23 C18 C19 C20 -0.7(4) . . . . ?
C17 C18 C19 C20 -173.5(3) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C18 C19 C20 Cl5 178.71(19) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
Cl5 C20 C21 C22 -178.0(2) . . . . ?
C19 C20 C21 Cl6 177.7(2) . . . . ?
Cl5 C20 C21 Cl6 -0.6(3) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
Cl6 C21 C22 C23 -178.18(18) . . . . ?
C21 C22 C23 C18 0.4(4) . . . . ?
C21 C22 C23 C24 174.7(2) . . . . ?
C19 C18 C23 C22 0.3(4) . . . . ?
C17 C18 C23 C22 174.7(2) . . . . ?
C19 C18 C23 C24 -175.3(2) . . . . ?
C17 C18 C23 C24 -0.9(3) . . . . ?
C1 N6 C24 N5 8.6(3) . . . . ?
C1 N6 C24 C23 -155.7(2) . . . . ?
C17 N5 C24 N6 -156.3(2) . . . . ?
B1 N5 C24 N6 10.1(4) . . . . ?
C17 N5 C24 C23 11.3(3) . . . . ?
B1 N5 C24 C23 177.6(2) . . . . ?
C22 C23 C24 N6 -14.5(4) . . . . ?
C18 C23 C24 N6 160.4(2) . . . . ?
C22 C23 C24 N5 179.2(2) . . . . ?
C18 C23 C24 N5 -5.9(3) . . . . ?
B1 O1 C25 C30 -83.4(3) . . . . ?
B1 O1 C25 C26 99.4(3) . . . . ?
O1 C25 C26 C27 177.7(2) . . . . ?
C30 C25 C26 C27 0.5(4) . . . . ?
C25 C26 C27 C28 0.1(5) . . . . ?
C26 C27 C28 C29 0.1(5) . . . . ?
C27 C28 C29 C30 -0.9(5) . . . . ?
O1 C25 C30 C29 -178.4(2) . . . . ?
C26 C25 C30 C29 -1.3(4) . . . . ?
C28 C29 C30 C25 1.4(4) . . . . ?
C25 O1 B1 N3 -162.5(2) . . . . ?
C25 O1 B1 N1 79.8(3) . . . . ?
C25 O1 B1 N5 -44.2(3) . . . . ?
C9 N3 B1 O1 -97.4(3) . . . . ?
C16 N3 B1 O1 93.2(3) . . . . ?
C9 N3 B1 N1 28.8(3) . . . . ?
C16 N3 B1 N1 -140.6(2) . . . . ?
C9 N3 B1 N5 136.8(2) . . . . ?
C16 N3 B1 N5 -32.6(3) . . . . ?
C8 N1 B1 O1 89.7(3) . . . . ?
C1 N1 B1 O1 -102.0(3) . . . . ?
C8 N1 B1 N3 -31.1(3) . . . . ?
C1 N1 B1 N3 137.2(2) . . . . ?
C8 N1 B1 N5 -139.8(2) . . . . ?
C1 N1 B1 N5 28.5(3) . . . . ?
C17 N5 B1 O1 -90.0(3) . . . . ?
C24 N5 B1 O1 104.9(3) . . . . ?
C17 N5 B1 N3 31.1(3) . . . . ?
C24 N5 B1 N3 -134.1(2) . . . . ?
C17 N5 B1 N1 139.1(2) . . . . ?
C24 N5 B1 N1 -26.0(3) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.072



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene/heptane'
####################################################################### 
# 
# 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_d19197_a
_database_code_depnum_ccdc_archive 'CCDC 2087096'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Cl-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 B Cl7 N6'
_chemical_formula_sum            'C24 H6 B Cl7 N6'
_chemical_formula_weight         637.31

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0941(8)
_cell_length_b                   7.4220(4)
_cell_length_c                   25.4950(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.487(2)
_cell_angle_gamma                90
_cell_volume                     2443.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9658
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.28

_exptl_crystal_description       needle
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.843
_shelx_estimated_absorpt_T_min   0.798
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6796
_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            48146
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.620
_diffrn_reflns_theta_max         27.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5655
_reflns_number_gt                4224
_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 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)+(0.0261P)²+2.3185P] 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         5655
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Cl1 Cl 0.61268(4) -0.25238(7) 0.33890(2) 0.02228(12) Uani 1 1 d . . . . .
Cl2 Cl 0.35680(5) 0.78053(10) 0.40917(3) 0.04312(19) Uani 1 1 d . . . . .
Cl3 Cl 0.56241(5) 0.78120(8) 0.49194(2) 0.02836(14) Uani 1 1 d . . . . .
Cl4 Cl 1.20618(4) 0.27806(9) 0.40996(2) 0.03201(15) Uani 1 1 d . . . . .
Cl5 Cl 1.20983(5) 0.16553(10) 0.29149(2) 0.03565(16) Uani 1 1 d . . . . .
Cl6 Cl 0.60103(5) 0.18415(10) 0.02422(2) 0.03478(16) Uani 1 1 d . . . . .
Cl7 Cl 0.37784(4) 0.29237(9) 0.04364(2) 0.02910(14) Uani 1 1 d . . . . .
N1 N 0.60290(13) 0.1212(2) 0.34802(7) 0.0153(4) Uani 1 1 d . . . . .
N2 N 0.76199(13) 0.1841(2) 0.40512(7) 0.0170(4) Uani 1 1 d . . . . .
N3 N 0.75975(13) 0.0100(2) 0.32667(7) 0.0152(4) Uani 1 1 d . . . . .
N4 N 0.77376(13) -0.0289(2) 0.23538(7) 0.0151(4) Uani 1 1 d . . . . .
N5 N 0.60875(13) 0.0135(2) 0.26171(7) 0.0146(4) Uani 1 1 d . . . . .
N6 N 0.46590(13) 0.1913(2) 0.27733(7) 0.0167(4) Uani 1 1 d . . . . .
C1 C 0.51276(16) 0.2086(3) 0.32820(8) 0.0166(4) Uani 1 1 d . . . . .
C2 C 0.50049(16) 0.3454(3) 0.36784(8) 0.0172(4) Uani 1 1 d . . . . .
C3 C 0.42611(17) 0.4783(3) 0.36939(9) 0.0209(5) Uani 1 1 d . . . . .
H3A H 0.364177 0.479956 0.344049 0.025 Uiso 1 1 calc R U . . .
C4 C 0.44471(16) 0.6078(3) 0.40877(9) 0.0221(5) Uani 1 1 d . . . . .
C5 C 0.53641(17) 0.6068(3) 0.44661(9) 0.0202(5) Uani 1 1 d . . . . .
C6 C 0.60993(17) 0.4745(3) 0.44610(8) 0.0192(5) Uani 1 1 d . . . . .
H6A H 0.671187 0.472767 0.471907 0.023 Uiso 1 1 calc R U . . .
C7 C 0.59182(16) 0.3433(3) 0.40664(8) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.65902(16) 0.2046(3) 0.39115(8) 0.0160(4) Uani 1 1 d . . . . .
C9 C 0.81115(16) 0.0967(3) 0.37049(8) 0.0159(4) Uani 1 1 d . . . . .
C10 C 0.91793(16) 0.1125(3) 0.36182(8) 0.0162(4) Uani 1 1 d . . . . .
C11 C 1.00531(16) 0.1842(3) 0.39286(8) 0.0188(5) Uani 1 1 d . . . . .
H11A H 1.003627 0.224026 0.428112 0.023 Uiso 1 1 calc R U . . .
C12 C 1.09510(16) 0.1961(3) 0.37104(9) 0.0205(5) Uani 1 1 d . . . . .
C13 C 1.09714(17) 0.1432(3) 0.31820(9) 0.0208(5) Uani 1 1 d . . . . .
C14 C 1.01031(16) 0.0727(3) 0.28665(8) 0.0180(4) Uani 1 1 d . . . . .
H14A H 1.011577 0.039127 0.250807 0.022 Uiso 1 1 calc R U . . .
C15 C 0.92105(16) 0.0524(3) 0.30906(8) 0.0157(4) Uani 1 1 d . . . . .
C16 C 0.81684(16) -0.0052(3) 0.28645(8) 0.0151(4) Uani 1 1 d . . . . .
C17 C 0.67061(16) -0.0051(3) 0.22385(8) 0.0149(4) Uani 1 1 d . . . . .
C18 C 0.60847(16) 0.0525(3) 0.17475(8) 0.0153(4) Uani 1 1 d . . . . .
C19 C 0.63544(16) 0.0731(3) 0.12464(8) 0.0178(4) Uani 1 1 d . . . . .
H19A H 0.701279 0.035603 0.117691 0.021 Uiso 1 1 calc R U . . .
C20 C 0.56391(17) 0.1495(3) 0.08539(8) 0.0199(5) Uani 1 1 d . . . . .
C21 C 0.46554(16) 0.2034(3) 0.09518(8) 0.0193(5) Uani 1 1 d . . . . .
C22 C 0.43913(16) 0.1884(3) 0.14563(8) 0.0184(4) Uani 1 1 d . . . . .
H22A H 0.373313 0.226995 0.152333 0.022 Uiso 1 1 calc R U . . .
C23 C 0.51194(16) 0.1151(3) 0.18613(8) 0.0165(4) Uani 1 1 d . . . . .
C24 C 0.51798(16) 0.1020(3) 0.24397(8) 0.0164(4) Uani 1 1 d . . . . .
B1 B 0.64633(18) -0.0248(3) 0.31875(9) 0.0153(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.840(2) . ?
Cl2 C4 1.724(2) . ?
Cl3 C5 1.731(2) . ?
Cl4 C12 1.731(2) . ?
Cl5 C13 1.732(2) . ?
Cl6 C20 1.728(2) . ?
Cl7 C21 1.727(2) . ?
N1 C8 1.366(3) . ?
N1 C1 1.369(3) . ?
N1 B1 1.481(3) . ?
N2 C9 1.343(3) . ?
N2 C8 1.345(3) . ?
N3 C9 1.366(3) . ?
N3 C16 1.370(3) . ?
N3 B1 1.488(3) . ?
N4 C16 1.343(3) . ?
N4 C17 1.346(3) . ?
N5 C17 1.365(3) . ?
N5 C24 1.368(3) . ?
N5 B1 1.484(3) . ?
N6 C1 1.346(3) . ?
N6 C24 1.349(3) . ?
C1 C2 1.460(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.421(3) . ?
C3 C4 1.382(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.411(3) . ?
C5 C6 1.377(3) . ?
C6 C7 1.392(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.451(3) . ?
C9 C10 1.456(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.424(3) . ?
C11 C12 1.384(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.408(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.391(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.455(3) . ?
C17 C18 1.441(3) . ?
C18 C19 1.389(3) . ?
C18 C23 1.421(3) . ?
C19 C20 1.375(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.410(3) . ?
C21 C22 1.390(3) . ?
C22 C23 1.395(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.467(3) . ?

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
C8 N1 C1 113.53(17) . . ?
C8 N1 B1 122.46(18) . . ?
C1 N1 B1 122.70(18) . . ?
C9 N2 C8 116.65(18) . . ?
C9 N3 C16 113.26(17) . . ?
C9 N3 B1 122.59(17) . . ?
C16 N3 B1 122.67(18) . . ?
C16 N4 C17 116.14(17) . . ?
C17 N5 C24 113.51(17) . . ?
C17 N5 B1 122.27(17) . . ?
C24 N5 B1 123.07(17) . . ?
C1 N6 C24 117.19(18) . . ?
N6 C1 N1 122.60(19) . . ?
N6 C1 C2 130.4(2) . . ?
N1 C1 C2 105.11(18) . . ?
C3 C2 C7 120.1(2) . . ?
C3 C2 C1 132.1(2) . . ?
C7 C2 C1 107.35(18) . . ?
C4 C3 C2 118.2(2) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 Cl2 118.92(18) . . ?
C5 C4 Cl2 119.58(17) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 Cl3 118.60(18) . . ?
C4 C5 Cl3 120.27(17) . . ?
C5 C6 C7 118.0(2) . . ?
C5 C6 H6A 121.0 . . ?
C7 C6 H6A 121.0 . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 C8 130.9(2) . . ?
C2 C7 C8 107.28(18) . . ?
N2 C8 N1 123.02(18) . . ?
N2 C8 C7 129.4(2) . . ?
N1 C8 C7 105.70(18) . . ?
N2 C9 N3 122.71(19) . . ?
N2 C9 C10 129.60(19) . . ?
N3 C9 C10 105.65(17) . . ?
C11 C10 C15 120.66(19) . . ?
C11 C10 C9 131.88(19) . . ?
C15 C10 C9 107.22(18) . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 H11A 120.9 . . ?
C10 C11 H11A 120.9 . . ?
C11 C12 C13 121.2(2) . . ?
C11 C12 Cl4 118.79(17) . . ?
C13 C12 Cl4 120.00(16) . . ?
C14 C13 C12 121.24(19) . . ?
C14 C13 Cl5 118.66(17) . . ?
C12 C13 Cl5 120.10(17) . . ?
C13 C14 C15 117.90(19) . . ?
C13 C14 H14A 121.0 . . ?
C15 C14 H14A 121.0 . . ?
C14 C15 C10 120.73(19) . . ?
C14 C15 C16 131.71(19) . . ?
C10 C15 C16 107.17(18) . . ?
N4 C16 N3 122.89(19) . . ?
N4 C16 C15 129.75(18) . . ?
N3 C16 C15 105.72(17) . . ?
N4 C17 N5 123.36(18) . . ?
N4 C17 C18 129.15(18) . . ?
N5 C17 C18 105.57(17) . . ?
C19 C18 C23 121.4(2) . . ?
C19 C18 C17 129.72(19) . . ?
C23 C18 C17 108.27(18) . . ?
C20 C19 C18 118.0(2) . . ?
C20 C19 H19A 121.0 . . ?
C18 C19 H19A 121.0 . . ?
C19 C20 C21 121.39(19) . . ?
C19 C20 Cl6 117.32(17) . . ?
C21 C20 Cl6 121.25(17) . . ?
C22 C21 C20 120.99(19) . . ?
C22 C21 Cl7 119.92(17) . . ?
C20 C21 Cl7 119.08(16) . . ?
C21 C22 C23 118.2(2) . . ?
C21 C22 H22A 120.9 . . ?
C23 C22 H22A 120.9 . . ?
C22 C23 C18 119.91(19) . . ?
C22 C23 C24 133.4(2) . . ?
C18 C23 C24 106.34(18) . . ?
N6 C24 N5 121.97(19) . . ?
N6 C24 C23 130.71(19) . . ?
N5 C24 C23 105.32(17) . . ?
N1 B1 N5 105.12(17) . . ?
N1 B1 N3 105.19(18) . . ?
N5 B1 N3 105.19(16) . . ?
N1 B1 Cl1 113.66(15) . . ?
N5 B1 Cl1 113.16(16) . . ?
N3 B1 Cl1 113.65(16) . . ?

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 -8.4(3) . . . . ?
C24 N6 C1 C2 153.7(2) . . . . ?
C8 N1 C1 N6 155.51(19) . . . . ?
B1 N1 C1 N6 -11.7(3) . . . . ?
C8 N1 C1 C2 -10.4(2) . . . . ?
B1 N1 C1 C2 -177.63(18) . . . . ?
N6 C1 C2 C3 13.5(4) . . . . ?
N1 C1 C2 C3 177.9(2) . . . . ?
N6 C1 C2 C7 -158.0(2) . . . . ?
N1 C1 C2 C7 6.4(2) . . . . ?
C7 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 C4 -169.5(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 Cl2 176.51(16) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
Cl2 C4 C5 C6 -177.56(17) . . . . ?
C3 C4 C5 Cl3 174.57(17) . . . . ?
Cl2 C4 C5 Cl3 -1.9(3) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
Cl3 C5 C6 C7 -174.77(15) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C5 C6 C7 C8 170.2(2) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C1 C2 C7 C6 171.47(18) . . . . ?
C3 C2 C7 C8 -173.37(18) . . . . ?
C1 C2 C7 C8 -0.7(2) . . . . ?
C9 N2 C8 N1 9.0(3) . . . . ?
C9 N2 C8 C7 -153.0(2) . . . . ?
C1 N1 C8 N2 -155.48(19) . . . . ?
B1 N1 C8 N2 11.7(3) . . . . ?
C1 N1 C8 C7 10.1(2) . . . . ?
B1 N1 C8 C7 177.31(18) . . . . ?
C6 C7 C8 N2 -12.1(4) . . . . ?
C2 C7 C8 N2 159.0(2) . . . . ?
C6 C7 C8 N1 -176.4(2) . . . . ?
C2 C7 C8 N1 -5.4(2) . . . . ?
C8 N2 C9 N3 -8.9(3) . . . . ?
C8 N2 C9 C10 152.5(2) . . . . ?
C16 N3 C9 N2 154.70(19) . . . . ?
B1 N3 C9 N2 -11.8(3) . . . . ?
C16 N3 C9 C10 -10.5(2) . . . . ?
B1 N3 C9 C10 -176.97(18) . . . . ?
N2 C9 C10 C11 17.7(4) . . . . ?
N3 C9 C10 C11 -178.5(2) . . . . ?
N2 C9 C10 C15 -156.6(2) . . . . ?
N3 C9 C10 C15 7.2(2) . . . . ?
C15 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 C12 -173.4(2) . . . . ?
C10 C11 C12 C13 2.3(3) . . . . ?
C10 C11 C12 Cl4 -177.81(17) . . . . ?
C11 C12 C13 C14 -1.9(4) . . . . ?
Cl4 C12 C13 C14 178.23(18) . . . . ?
C11 C12 C13 Cl5 178.23(18) . . . . ?
Cl4 C12 C13 Cl5 -1.7(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
Cl5 C13 C14 C15 178.77(17) . . . . ?
C13 C14 C15 C10 3.6(3) . . . . ?
C13 C14 C15 C16 175.5(2) . . . . ?
C11 C10 C15 C14 -3.2(3) . . . . ?
C9 C10 C15 C14 171.83(19) . . . . ?
C11 C10 C15 C16 -176.88(19) . . . . ?
C9 C10 C15 C16 -1.8(2) . . . . ?
C17 N4 C16 N3 11.5(3) . . . . ?
C17 N4 C16 C15 -151.7(2) . . . . ?
C9 N3 C16 N4 -157.33(19) . . . . ?
B1 N3 C16 N4 9.1(3) . . . . ?
C9 N3 C16 C15 9.4(2) . . . . ?
B1 N3 C16 C15 175.83(18) . . . . ?
C14 C15 C16 N4 -11.5(4) . . . . ?
C10 C15 C16 N4 161.2(2) . . . . ?
C14 C15 C16 N3 -176.9(2) . . . . ?
C10 C15 C16 N3 -4.2(2) . . . . ?
C16 N4 C17 N5 -10.3(3) . . . . ?
C16 N4 C17 C18 151.6(2) . . . . ?
C24 N5 C17 N4 156.41(19) . . . . ?
B1 N5 C17 N4 -11.7(3) . . . . ?
C24 N5 C17 C18 -9.1(2) . . . . ?
B1 N5 C17 C18 -177.21(18) . . . . ?
N4 C17 C18 C19 10.5(4) . . . . ?
N5 C17 C18 C19 174.9(2) . . . . ?
N4 C17 C18 C23 -160.7(2) . . . . ?
N5 C17 C18 C23 3.6(2) . . . . ?
C23 C18 C19 C20 -2.7(3) . . . . ?
C17 C18 C19 C20 -173.0(2) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C18 C19 C20 Cl6 176.94(17) . . . . ?
C19 C20 C21 C22 2.9(3) . . . . ?
Cl6 C20 C21 C22 -174.81(17) . . . . ?
C19 C20 C21 Cl7 -178.10(17) . . . . ?
Cl6 C20 C21 Cl7 4.2(3) . . . . ?
C20 C21 C22 C23 -1.3(3) . . . . ?
Cl7 C21 C22 C23 179.73(16) . . . . ?
C21 C22 C23 C18 -2.2(3) . . . . ?
C21 C22 C23 C24 169.8(2) . . . . ?
C19 C18 C23 C22 4.3(3) . . . . ?
C17 C18 C23 C22 176.42(19) . . . . ?
C19 C18 C23 C24 -169.68(19) . . . . ?
C17 C18 C23 C24 2.4(2) . . . . ?
C1 N6 C24 N5 7.7(3) . . . . ?
C1 N6 C24 C23 -153.7(2) . . . . ?
C17 N5 C24 N6 -154.93(19) . . . . ?
B1 N5 C24 N6 13.1(3) . . . . ?
C17 N5 C24 C23 10.6(2) . . . . ?
B1 N5 C24 C23 178.59(18) . . . . ?
C22 C23 C24 N6 -16.7(4) . . . . ?
C18 C23 C24 N6 156.2(2) . . . . ?
C22 C23 C24 N5 179.6(2) . . . . ?
C18 C23 C24 N5 -7.6(2) . . . . ?
C8 N1 B1 N5 -138.47(18) . . . . ?
C1 N1 B1 N5 27.6(3) . . . . ?
C8 N1 B1 N3 -27.7(3) . . . . ?
C1 N1 B1 N3 138.35(18) . . . . ?
C8 N1 B1 Cl1 97.3(2) . . . . ?
C1 N1 B1 Cl1 -96.7(2) . . . . ?
C17 N5 B1 N1 138.61(19) . . . . ?
C24 N5 B1 N1 -28.4(3) . . . . ?
C17 N5 B1 N3 27.8(3) . . . . ?
C24 N5 B1 N3 -139.15(19) . . . . ?
C17 N5 B1 Cl1 -96.8(2) . . . . ?
C24 N5 B1 Cl1 96.2(2) . . . . ?
C9 N3 B1 N1 27.8(3) . . . . ?
C16 N3 B1 N1 -137.43(19) . . . . ?
C9 N3 B1 N5 138.51(19) . . . . ?
C16 N3 B1 N5 -26.7(3) . . . . ?
C9 N3 B1 Cl1 -97.2(2) . . . . ?
C16 N3 B1 Cl1 97.6(2) . . . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.071



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichlorobenzene/heptane'
####################################################################### 
# 
# 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_d19194_a
_database_code_depnum_ccdc_archive 'CCDC 2087098'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        PhO-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H11 B Cl6 N6 O'
_chemical_formula_sum            'C30 H11 B Cl6 N6 O'
_chemical_formula_weight         694.96

# start Validation Reply Form
_vrf_RINTA01_d19194_a            
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Crystals are very weakly diffracting at higher angles.
;
# 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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                   13.118(3)
_cell_length_b                   14.899(2)
_cell_length_c                   14.576(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.581(9)
_cell_angle_gamma                90
_cell_volume                     2830.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    873
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      18.61

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.647
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6619
_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 ImuS'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25715
_diffrn_reflns_av_unetI/netI     0.2027
_diffrn_reflns_av_R_equivalents  0.2229
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.563
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4992
_reflns_number_gt                2194
_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 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)+(0.0296P)²] 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         4992
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1968
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
Cl1 Cl 0.94724(14) 0.67488(12) 0.69342(13) 0.0545(6) Uani 1 1 d . . . . .
Cl2 Cl 0.90884(14) 0.46939(11) 0.72849(12) 0.0476(5) Uani 1 1 d . . . . .
Cl3 Cl 0.18465(14) 0.21430(10) 0.56131(11) 0.0429(5) Uani 1 1 d . . . . .
Cl4 Cl -0.01350(13) 0.33448(10) 0.53181(11) 0.0408(5) Uani 1 1 d . . . . .
Cl5 Cl 0.11009(15) 0.99078(11) 0.40898(12) 0.0505(6) Uani 1 1 d . . . . .
Cl6 Cl 0.33566(14) 1.06675(10) 0.43405(11) 0.0365(5) Uani 1 1 d . . . . .
O1 O 0.3587(3) 0.6734(2) 0.8575(2) 0.0271(11) Uani 1 1 d . . . . .
N1 N 0.4867(4) 0.6482(3) 0.7460(3) 0.0189(12) Uani 1 1 d . . . . .
N2 N 0.4650(4) 0.4894(3) 0.7287(3) 0.0224(12) Uani 1 1 d . . . . .
N3 N 0.3201(4) 0.5871(3) 0.7211(3) 0.0193(12) Uani 1 1 d . . . . .
N4 N 0.1868(4) 0.6756(3) 0.6439(3) 0.0214(12) Uani 1 1 d . . . . .
N5 N 0.3471(4) 0.7420(3) 0.7013(3) 0.0186(12) Uani 1 1 d . . . . .
N6 N 0.5168(4) 0.7912(3) 0.6849(3) 0.0233(13) Uani 1 1 d . . . . .
C1 C 0.5510(5) 0.7115(4) 0.7185(4) 0.0228(16) Uani 1 1 d . . . . .
C2 C 0.6505(5) 0.6667(4) 0.7138(4) 0.0236(16) Uani 1 1 d . . . . .
C3 C 0.7455(5) 0.6982(4) 0.6985(4) 0.0257(16) Uani 1 1 d . . . . .
H3A H 0.756066 0.759472 0.684309 0.031 Uiso 1 1 calc R U . . .
C4 C 0.8246(5) 0.6372(4) 0.7046(4) 0.0288(16) Uani 1 1 d . . . . .
C5 C 0.8091(5) 0.5460(4) 0.7199(4) 0.0322(17) Uani 1 1 d . . . . .
C6 C 0.7117(5) 0.5134(4) 0.7297(3) 0.0274(16) Uani 1 1 d . . . . .
H6A H 0.699748 0.450925 0.736392 0.033 Uiso 1 1 calc R U . . .
C7 C 0.6331(5) 0.5745(4) 0.7294(4) 0.0214(15) Uani 1 1 d . . . . .
C8 C 0.5253(5) 0.5631(4) 0.7409(4) 0.0228(16) Uani 1 1 d . . . . .
C9 C 0.3639(5) 0.5046(4) 0.7126(4) 0.0195(15) Uani 1 1 d . . . . .
C10 C 0.2819(5) 0.4478(4) 0.6678(4) 0.0227(16) Uani 1 1 d . . . . .
C11 C 0.2794(5) 0.3589(4) 0.6398(4) 0.0252(16) Uani 1 1 d . . . . .
H11A H 0.338907 0.322346 0.649900 0.030 Uiso 1 1 calc R U . . .
C12 C 0.1880(5) 0.3245(4) 0.5967(4) 0.0308(17) Uani 1 1 d . . . . .
C13 C 0.1014(5) 0.3791(4) 0.5803(4) 0.0278(16) Uani 1 1 d . . . . .
C14 C 0.1051(5) 0.4693(4) 0.6010(4) 0.0230(15) Uani 1 1 d . . . . .
H14A H 0.047247 0.506769 0.584709 0.028 Uiso 1 1 calc R U . . .
C15 C 0.1960(5) 0.5046(3) 0.6464(4) 0.0211(15) Uani 1 1 d . . . . .
C16 C 0.2261(5) 0.5949(4) 0.6735(4) 0.0205(15) Uani 1 1 d . . . . .
C17 C 0.2513(5) 0.7460(4) 0.6524(4) 0.0226(15) Uani 1 1 d . . . . .
C18 C 0.2519(5) 0.8282(4) 0.5979(4) 0.0233(15) Uani 1 1 d . . . . .
C19 C 0.1749(5) 0.8677(4) 0.5362(4) 0.0285(16) Uani 1 1 d . . . . .
H19A H 0.107016 0.844498 0.528139 0.034 Uiso 1 1 calc R U . . .
C20 C 0.2026(5) 0.9423(4) 0.4872(4) 0.0287(17) Uani 1 1 d . . . . .
C21 C 0.3022(5) 0.9759(4) 0.4993(4) 0.0261(16) Uani 1 1 d . . . . .
C22 C 0.3788(5) 0.9366(3) 0.5590(4) 0.0216(15) Uani 1 1 d . . . . .
H22A H 0.446954 0.959336 0.565694 0.026 Uiso 1 1 calc R U . . .
C23 C 0.3517(5) 0.8622(4) 0.6089(4) 0.0207(15) Uani 1 1 d . . . . .
C24 C 0.4141(5) 0.8029(3) 0.6714(4) 0.0190(15) Uani 1 1 d . . . . .
C25 C 0.3797(5) 0.7525(4) 0.9050(4) 0.0215(16) Uani 1 1 d . . . . .
C26 C 0.3005(6) 0.8109(4) 0.9134(4) 0.0369(19) Uani 1 1 d . . . . .
H26A H 0.233694 0.797335 0.884460 0.044 Uiso 1 1 calc R U . . .
C27 C 0.3170(7) 0.8886(5) 0.9631(5) 0.051(2) Uani 1 1 d . . . . .
H27A H 0.261800 0.928562 0.969192 0.061 Uiso 1 1 calc R U . . .
C28 C 0.4140(8) 0.9082(5) 1.0041(5) 0.057(3) Uani 1 1 d . . . . .
H28A H 0.426240 0.962372 1.037943 0.069 Uiso 1 1 calc R U . . .
C29 C 0.4924(7) 0.8503(5) 0.9964(4) 0.050(2) Uani 1 1 d . . . . .
H29A H 0.558993 0.864083 1.025665 0.061 Uiso 1 1 calc R U . . .
C30 C 0.4769(6) 0.7710(4) 0.9463(4) 0.0342(18) Uani 1 1 d . . . . .
H30A H 0.531999 0.730717 0.940793 0.041 Uiso 1 1 calc R U . . .
B1 B 0.3790(6) 0.6653(4) 0.7646(5) 0.0226(18) 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 C4 1.730(6) . ?
Cl2 C5 1.730(6) . ?
Cl3 C12 1.721(6) . ?
Cl4 C13 1.723(6) . ?
Cl5 C20 1.726(6) . ?
Cl6 C21 1.740(6) . ?
O1 C25 1.379(6) . ?
O1 B1 1.415(7) . ?
N1 C1 1.357(7) . ?
N1 C8 1.371(7) . ?
N1 B1 1.490(8) . ?
N2 C9 1.340(7) . ?
N2 C8 1.354(7) . ?
N3 C16 1.349(7) . ?
N3 C9 1.367(6) . ?
N3 B1 1.498(7) . ?
N4 C17 1.344(7) . ?
N4 C16 1.358(6) . ?
N5 C24 1.368(7) . ?
N5 C17 1.374(7) . ?
N5 B1 1.498(7) . ?
N6 C1 1.342(7) . ?
N6 C24 1.351(7) . ?
C1 C2 1.475(8) . ?
C2 C3 1.374(8) . ?
C2 C7 1.414(7) . ?
C3 C4 1.374(8) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(8) . ?
C5 C6 1.390(8) . ?
C6 C7 1.375(8) . ?
C6 H6A 0.9500 . ?
C7 C8 1.453(8) . ?
C9 C10 1.463(7) . ?
C10 C11 1.385(7) . ?
C10 C15 1.416(7) . ?
C11 C12 1.386(7) . ?
C11 H11A 0.9500 . ?
C12 C13 1.395(8) . ?
C13 C14 1.377(7) . ?
C14 C15 1.398(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.444(7) . ?
C17 C18 1.460(7) . ?
C18 C23 1.395(8) . ?
C18 C19 1.402(7) . ?
C19 C20 1.392(7) . ?
C19 H19A 0.9500 . ?
C20 C21 1.391(8) . ?
C21 C22 1.381(7) . ?
C22 C23 1.395(7) . ?
C22 H22A 0.9500 . ?
C23 C24 1.453(7) . ?
C25 C26 1.371(8) . ?
C25 C30 1.373(8) . ?
C26 C27 1.370(8) . ?
C26 H26A 0.9500 . ?
C27 C28 1.374(10) . ?
C27 H27A 0.9500 . ?
C28 C29 1.357(10) . ?
C28 H28A 0.9500 . ?
C29 C30 1.391(8) . ?
C29 H29A 0.9500 . ?
C30 H30A 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
C25 O1 B1 120.3(4) . . ?
C1 N1 C8 112.3(5) . . ?
C1 N1 B1 124.7(5) . . ?
C8 N1 B1 122.2(5) . . ?
C9 N2 C8 116.0(5) . . ?
C16 N3 C9 113.5(5) . . ?
C16 N3 B1 123.2(5) . . ?
C9 N3 B1 122.4(5) . . ?
C17 N4 C16 116.7(5) . . ?
C24 N5 C17 112.9(5) . . ?
C24 N5 B1 123.9(5) . . ?
C17 N5 B1 121.8(5) . . ?
C1 N6 C24 116.9(5) . . ?
N6 C1 N1 122.0(6) . . ?
N6 C1 C2 130.1(6) . . ?
N1 C1 C2 106.4(5) . . ?
C3 C2 C7 121.6(6) . . ?
C3 C2 C1 132.6(6) . . ?
C7 C2 C1 105.8(6) . . ?
C2 C3 C4 117.1(6) . . ?
C2 C3 H3A 121.4 . . ?
C4 C3 H3A 121.4 . . ?
C3 C4 C5 122.1(6) . . ?
C3 C4 Cl1 118.9(5) . . ?
C5 C4 Cl1 119.0(5) . . ?
C6 C5 C4 120.6(6) . . ?
C6 C5 Cl2 117.3(5) . . ?
C4 C5 Cl2 122.1(5) . . ?
C7 C6 C5 117.7(6) . . ?
C7 C6 H6A 121.1 . . ?
C5 C6 H6A 121.1 . . ?
C6 C7 C2 120.6(6) . . ?
C6 C7 C8 131.3(6) . . ?
C2 C7 C8 108.0(5) . . ?
N2 C8 N1 122.9(6) . . ?
N2 C8 C7 130.0(6) . . ?
N1 C8 C7 105.6(5) . . ?
N2 C9 N3 123.6(5) . . ?
N2 C9 C10 130.0(5) . . ?
N3 C9 C10 105.4(5) . . ?
C11 C10 C15 121.0(6) . . ?
C11 C10 C9 132.6(6) . . ?
C15 C10 C9 106.1(5) . . ?
C10 C11 C12 118.5(6) . . ?
C10 C11 H11A 120.8 . . ?
C12 C11 H11A 120.8 . . ?
C11 C12 C13 120.5(5) . . ?
C11 C12 Cl3 118.7(5) . . ?
C13 C12 Cl3 120.8(5) . . ?
C14 C13 C12 121.6(6) . . ?
C14 C13 Cl4 118.3(5) . . ?
C12 C13 Cl4 120.1(5) . . ?
C13 C14 C15 118.5(5) . . ?
C13 C14 H14A 120.7 . . ?
C15 C14 H14A 120.7 . . ?
C14 C15 C10 119.5(5) . . ?
C14 C15 C16 132.2(6) . . ?
C10 C15 C16 108.1(5) . . ?
N3 C16 N4 122.1(5) . . ?
N3 C16 C15 105.4(5) . . ?
N4 C16 C15 130.9(5) . . ?
N4 C17 N5 122.8(5) . . ?
N4 C17 C18 130.4(6) . . ?
N5 C17 C18 104.9(5) . . ?
C23 C18 C19 121.3(5) . . ?
C23 C18 C17 107.8(5) . . ?
C19 C18 C17 130.7(6) . . ?
C20 C19 C18 116.9(6) . . ?
C20 C19 H19A 121.5 . . ?
C18 C19 H19A 121.5 . . ?
C21 C20 C19 121.3(6) . . ?
C21 C20 Cl5 120.8(5) . . ?
C19 C20 Cl5 117.9(5) . . ?
C22 C21 C20 122.2(5) . . ?
C22 C21 Cl6 117.6(5) . . ?
C20 C21 Cl6 120.2(5) . . ?
C21 C22 C23 117.0(6) . . ?
C21 C22 H22A 121.5 . . ?
C23 C22 H22A 121.5 . . ?
C18 C23 C22 121.4(5) . . ?
C18 C23 C24 107.8(5) . . ?
C22 C23 C24 130.7(6) . . ?
N6 C24 N5 122.3(5) . . ?
N6 C24 C23 130.6(6) . . ?
N5 C24 C23 105.5(5) . . ?
C26 C25 C30 120.6(6) . . ?
C26 C25 O1 118.5(6) . . ?
C30 C25 O1 120.9(6) . . ?
C27 C26 C25 120.5(7) . . ?
C27 C26 H26A 119.7 . . ?
C25 C26 H26A 119.7 . . ?
C26 C27 C28 119.5(7) . . ?
C26 C27 H27A 120.3 . . ?
C28 C27 H27A 120.3 . . ?
C29 C28 C27 120.1(7) . . ?
C29 C28 H28A 120.0 . . ?
C27 C28 H28A 120.0 . . ?
C28 C29 C30 121.1(7) . . ?
C28 C29 H29A 119.4 . . ?
C30 C29 H29A 119.4 . . ?
C25 C30 C29 118.2(7) . . ?
C25 C30 H30A 120.9 . . ?
C29 C30 H30A 120.9 . . ?
O1 B1 N1 118.3(5) . . ?
O1 B1 N3 109.1(5) . . ?
N1 B1 N3 104.1(5) . . ?
O1 B1 N5 117.1(5) . . ?
N1 B1 N5 102.8(5) . . ?
N3 B1 N5 103.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C24 N6 C1 N1 -6.1(8) . . . . ?
C24 N6 C1 C2 158.3(5) . . . . ?
C8 N1 C1 N6 154.4(5) . . . . ?
B1 N1 C1 N6 -15.7(8) . . . . ?
C8 N1 C1 C2 -13.2(6) . . . . ?
B1 N1 C1 C2 176.7(5) . . . . ?
N6 C1 C2 C3 20.6(10) . . . . ?
N1 C1 C2 C3 -173.2(6) . . . . ?
N6 C1 C2 C7 -159.5(5) . . . . ?
N1 C1 C2 C7 6.7(6) . . . . ?
C7 C2 C3 C4 -3.9(8) . . . . ?
C1 C2 C3 C4 176.0(5) . . . . ?
C2 C3 C4 C5 3.9(9) . . . . ?
C2 C3 C4 Cl1 -175.8(4) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
Cl1 C4 C5 C6 179.7(4) . . . . ?
C3 C4 C5 Cl2 -179.5(5) . . . . ?
Cl1 C4 C5 Cl2 0.2(7) . . . . ?
C4 C5 C6 C7 -3.9(8) . . . . ?
Cl2 C5 C6 C7 175.6(4) . . . . ?
C5 C6 C7 C2 3.9(8) . . . . ?
C5 C6 C7 C8 -177.8(6) . . . . ?
C3 C2 C7 C6 0.0(8) . . . . ?
C1 C2 C7 C6 -179.9(5) . . . . ?
C3 C2 C7 C8 -178.6(5) . . . . ?
C1 C2 C7 C8 1.4(6) . . . . ?
C9 N2 C8 N1 6.4(8) . . . . ?
C9 N2 C8 C7 -157.3(6) . . . . ?
C1 N1 C8 N2 -153.2(5) . . . . ?
B1 N1 C8 N2 17.3(8) . . . . ?
C1 N1 C8 C7 14.0(6) . . . . ?
B1 N1 C8 C7 -175.6(5) . . . . ?
C6 C7 C8 N2 -21.6(10) . . . . ?
C2 C7 C8 N2 156.9(5) . . . . ?
C6 C7 C8 N1 172.5(6) . . . . ?
C2 C7 C8 N1 -9.0(6) . . . . ?
C8 N2 C9 N3 -9.7(8) . . . . ?
C8 N2 C9 C10 157.5(6) . . . . ?
C16 N3 C9 N2 158.9(5) . . . . ?
B1 N3 C9 N2 -10.5(9) . . . . ?
C16 N3 C9 C10 -11.0(6) . . . . ?
B1 N3 C9 C10 179.6(5) . . . . ?
N2 C9 C10 C11 9.8(11) . . . . ?
N3 C9 C10 C11 178.8(6) . . . . ?
N2 C9 C10 C15 -164.4(6) . . . . ?
N3 C9 C10 C15 4.6(6) . . . . ?
C15 C10 C11 C12 -5.2(9) . . . . ?
C9 C10 C11 C12 -178.7(6) . . . . ?
C10 C11 C12 C13 1.5(9) . . . . ?
C10 C11 C12 Cl3 179.7(4) . . . . ?
C11 C12 C13 C14 3.9(9) . . . . ?
Cl3 C12 C13 C14 -174.3(4) . . . . ?
C11 C12 C13 Cl4 -176.8(5) . . . . ?
Cl3 C12 C13 Cl4 5.0(8) . . . . ?
C12 C13 C14 C15 -5.3(9) . . . . ?
Cl4 C13 C14 C15 175.4(4) . . . . ?
C13 C14 C15 C10 1.5(8) . . . . ?
C13 C14 C15 C16 176.6(6) . . . . ?
C11 C10 C15 C14 3.7(9) . . . . ?
C9 C10 C15 C14 178.8(5) . . . . ?
C11 C10 C15 C16 -172.4(5) . . . . ?
C9 C10 C15 C16 2.6(6) . . . . ?
C9 N3 C16 N4 -154.6(5) . . . . ?
B1 N3 C16 N4 14.7(9) . . . . ?
C9 N3 C16 C15 12.6(7) . . . . ?
B1 N3 C16 C15 -178.2(5) . . . . ?
C17 N4 C16 N3 9.4(8) . . . . ?
C17 N4 C16 C15 -154.1(6) . . . . ?
C14 C15 C16 N3 175.6(6) . . . . ?
C10 C15 C16 N3 -8.9(6) . . . . ?
C14 C15 C16 N4 -18.9(11) . . . . ?
C10 C15 C16 N4 156.7(6) . . . . ?
C16 N4 C17 N5 -10.3(8) . . . . ?
C16 N4 C17 C18 151.5(6) . . . . ?
C24 N5 C17 N4 154.3(5) . . . . ?
B1 N5 C17 N4 -12.7(9) . . . . ?
C24 N5 C17 C18 -11.4(6) . . . . ?
B1 N5 C17 C18 -178.4(5) . . . . ?
N4 C17 C18 C23 -157.0(6) . . . . ?
N5 C17 C18 C23 7.3(6) . . . . ?
N4 C17 C18 C19 16.8(11) . . . . ?
N5 C17 C18 C19 -179.0(6) . . . . ?
C23 C18 C19 C20 -0.5(8) . . . . ?
C17 C18 C19 C20 -173.5(6) . . . . ?
C18 C19 C20 C21 0.0(9) . . . . ?
C18 C19 C20 Cl5 178.7(4) . . . . ?
C19 C20 C21 C22 1.0(9) . . . . ?
Cl5 C20 C21 C22 -177.7(4) . . . . ?
C19 C20 C21 Cl6 177.6(4) . . . . ?
Cl5 C20 C21 Cl6 -1.0(7) . . . . ?
C20 C21 C22 C23 -1.4(8) . . . . ?
Cl6 C21 C22 C23 -178.1(4) . . . . ?
C19 C18 C23 C22 0.0(8) . . . . ?
C17 C18 C23 C22 174.5(5) . . . . ?
C19 C18 C23 C24 -175.5(5) . . . . ?
C17 C18 C23 C24 -1.1(6) . . . . ?
C21 C22 C23 C18 0.9(8) . . . . ?
C21 C22 C23 C24 175.3(5) . . . . ?
C1 N6 C24 N5 8.4(8) . . . . ?
C1 N6 C24 C23 -154.9(5) . . . . ?
C17 N5 C24 N6 -156.1(5) . . . . ?
B1 N5 C24 N6 10.6(8) . . . . ?
C17 N5 C24 C23 10.8(6) . . . . ?
B1 N5 C24 C23 177.5(5) . . . . ?
C18 C23 C24 N6 159.8(6) . . . . ?
C22 C23 C24 N6 -15.2(10) . . . . ?
C18 C23 C24 N5 -5.6(6) . . . . ?
C22 C23 C24 N5 179.4(5) . . . . ?
B1 O1 C25 C26 99.5(7) . . . . ?
B1 O1 C25 C30 -83.0(7) . . . . ?
C30 C25 C26 C27 -0.1(9) . . . . ?
O1 C25 C26 C27 177.4(5) . . . . ?
C25 C26 C27 C28 0.6(10) . . . . ?
C26 C27 C28 C29 -0.9(11) . . . . ?
C27 C28 C29 C30 0.8(11) . . . . ?
C26 C25 C30 C29 -0.1(9) . . . . ?
O1 C25 C30 C29 -177.5(5) . . . . ?
C28 C29 C30 C25 -0.3(9) . . . . ?
C25 O1 B1 N1 79.3(7) . . . . ?
C25 O1 B1 N3 -162.1(5) . . . . ?
C25 O1 B1 N5 -44.6(8) . . . . ?
C1 N1 B1 O1 -101.6(6) . . . . ?
C8 N1 B1 O1 89.2(6) . . . . ?
C1 N1 B1 N3 137.2(5) . . . . ?
C8 N1 B1 N3 -32.0(7) . . . . ?
C1 N1 B1 N5 29.2(7) . . . . ?
C8 N1 B1 N5 -140.0(5) . . . . ?
C16 N3 B1 O1 93.3(7) . . . . ?
C9 N3 B1 O1 -98.3(6) . . . . ?
C16 N3 B1 N1 -139.5(5) . . . . ?
C9 N3 B1 N1 28.9(7) . . . . ?
C16 N3 B1 N5 -32.2(8) . . . . ?
C9 N3 B1 N5 136.1(5) . . . . ?
C24 N5 B1 O1 105.1(7) . . . . ?
C17 N5 B1 O1 -89.4(7) . . . . ?
C24 N5 B1 N1 -26.4(7) . . . . ?
C17 N5 B1 N1 139.1(5) . . . . ?
C24 N5 B1 N3 -134.7(5) . . . . ?
C17 N5 B1 N3 30.9(8) . . . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.094



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichlorobenzene/dimethoxybezene/pentane'
####################################################################### 
# 
# 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_d19208_a
_database_code_depnum_ccdc_archive 'CCDC 2087102'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        NaphO-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H13 B Cl6 N6 O'
_chemical_formula_sum            'C34 H13 B Cl6 N6 O'
_chemical_formula_weight         745.01

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'
O O 0.0106 0.0060 '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           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                   10.4119(4)
_cell_length_b                   22.7476(9)
_cell_length_c                   13.0866(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.274(1)
_cell_angle_gamma                90
_cell_volume                     3067.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      26.31

_exptl_crystal_description       Shard
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.603
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7207
_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            46522
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.790
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7066
_reflns_number_gt                5204
_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 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)+(0.0337P)²+2.6223P] 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         7066
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Cl1 Cl 1.38829(5) 0.45609(3) 0.61038(5) 0.03256(14) Uani 1 1 d . . . . .
Cl2 Cl 1.40186(5) 0.33196(3) 0.71741(5) 0.03601(16) Uani 1 1 d . . . . .
Cl3 Cl 0.93297(6) 0.01234(3) 0.34491(5) 0.03730(16) Uani 1 1 d . . . . .
Cl4 Cl 0.75024(6) 0.03421(3) 0.13542(5) 0.03280(14) Uani 1 1 d . . . . .
Cl5 Cl 0.57505(6) 0.46359(3) -0.12920(4) 0.03191(14) Uani 1 1 d . . . . .
Cl6 Cl 0.72490(6) 0.56651(3) -0.00034(5) 0.03726(16) Uani 1 1 d . . . . .
O1 O 0.61327(14) 0.34100(7) 0.46992(11) 0.0264(4) Uani 1 1 d . . . . .
N1 N 0.84598(16) 0.34519(8) 0.47237(13) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.90650(17) 0.24611(8) 0.51378(14) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.73331(16) 0.26732(8) 0.37847(13) 0.0201(4) Uani 1 1 d . . . . .
N4 N 0.64960(17) 0.28400(8) 0.20121(14) 0.0219(4) Uani 1 1 d . . . . .
N5 N 0.71417(17) 0.36367(8) 0.31347(13) 0.0210(4) Uani 1 1 d . . . . .
N6 N 0.86843(17) 0.43494(8) 0.38314(14) 0.0225(4) Uani 1 1 d . . . . .
C1 C 0.9094(2) 0.39642(10) 0.45859(16) 0.0213(5) Uani 1 1 d . . . . .
C2 C 1.0344(2) 0.39209(10) 0.52371(16) 0.0209(4) Uani 1 1 d . . . . .
C3 C 1.1404(2) 0.42991(10) 0.53703(16) 0.0229(5) Uani 1 1 d . . . . .
H3A H 1.135275 0.467909 0.506615 0.027 Uiso 1 1 calc R U . . .
C4 C 1.2534(2) 0.41062(10) 0.59576(17) 0.0235(5) Uani 1 1 d . . . . .
C5 C 1.2614(2) 0.35453(10) 0.64106(17) 0.0243(5) Uani 1 1 d . . . . .
C6 C 1.1582(2) 0.31579(10) 0.62512(17) 0.0240(5) Uani 1 1 d . . . . .
H6A H 1.165060 0.277253 0.653362 0.029 Uiso 1 1 calc R U . . .
C7 C 1.0437(2) 0.33508(10) 0.56630(16) 0.0216(5) Uani 1 1 d . . . . .
C8 C 0.9256(2) 0.30399(10) 0.52547(16) 0.0219(5) Uani 1 1 d . . . . .
C9 C 0.8164(2) 0.22912(10) 0.43510(16) 0.0216(5) Uani 1 1 d . . . . .
C10 C 0.8127(2) 0.17556(10) 0.37580(17) 0.0226(5) Uani 1 1 d . . . . .
C11 C 0.8777(2) 0.12248(10) 0.39506(18) 0.0253(5) Uani 1 1 d . . . . .
H11A H 0.933064 0.115833 0.458297 0.030 Uiso 1 1 calc R U . . .
C12 C 0.8596(2) 0.07994(10) 0.31998(18) 0.0252(5) Uani 1 1 d . . . . .
C13 C 0.7802(2) 0.09026(10) 0.22483(17) 0.0244(5) Uani 1 1 d . . . . .
C14 C 0.7191(2) 0.14347(10) 0.20338(17) 0.0223(5) Uani 1 1 d . . . . .
H14A H 0.667725 0.150464 0.138435 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7345(2) 0.18663(10) 0.27925(17) 0.0216(5) Uani 1 1 d . . . . .
C16 C 0.69204(19) 0.24755(10) 0.28051(16) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.66567(19) 0.34171(10) 0.21840(16) 0.0218(5) Uani 1 1 d . . . . .
C18 C 0.6694(2) 0.39117(10) 0.14728(17) 0.0223(5) Uani 1 1 d . . . . .
C19 C 0.6229(2) 0.39875(10) 0.04303(17) 0.0238(5) Uani 1 1 d . . . . .
H19A H 0.579835 0.367640 0.003535 0.029 Uiso 1 1 calc R U . . .
C20 C 0.6409(2) 0.45266(10) -0.00177(17) 0.0255(5) Uani 1 1 d . . . . .
C21 C 0.7074(2) 0.49867(10) 0.05536(18) 0.0257(5) Uani 1 1 d . . . . .
C22 C 0.7562(2) 0.49123(10) 0.15860(18) 0.0250(5) Uani 1 1 d . . . . .
H22A H 0.802287 0.521968 0.196994 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7361(2) 0.43785(10) 0.20446(17) 0.0228(5) Uani 1 1 d . . . . .
C24 C 0.7737(2) 0.41658(10) 0.30926(17) 0.0225(5) Uani 1 1 d . . . . .
C25 C 0.4883(2) 0.32300(11) 0.43295(17) 0.0249(5) Uani 1 1 d . . . . .
C26 C 0.4447(2) 0.26942(11) 0.47142(19) 0.0307(5) Uani 1 1 d . . . . .
H26A H 0.501966 0.246434 0.518461 0.037 Uiso 1 1 calc R U . . .
C27 C 0.3206(2) 0.25090(11) 0.44094(19) 0.0338(6) Uani 1 1 d . . . . .
H27A H 0.291775 0.215045 0.467117 0.041 Uiso 1 1 calc R U . . .
C28 C 0.2348(2) 0.28447(11) 0.37093(18) 0.0288(5) Uani 1 1 d . . . . .
C29 C 0.1040(2) 0.26604(13) 0.3363(2) 0.0390(6) Uani 1 1 d . . . . .
H29A H 0.073217 0.230166 0.360922 0.047 Uiso 1 1 calc R U . . .
C30 C 0.0241(2) 0.29916(14) 0.2690(2) 0.0421(7) Uani 1 1 d . . . . .
H30A H -0.062123 0.286308 0.246504 0.051 Uiso 1 1 calc R U . . .
C31 C 0.0676(3) 0.35247(14) 0.2320(2) 0.0448(7) Uani 1 1 d . . . . .
H31A H 0.010430 0.375403 0.184742 0.054 Uiso 1 1 calc R U . . .
C32 C 0.1916(3) 0.37164(13) 0.2634(2) 0.0395(6) Uani 1 1 d . . . . .
H32A H 0.219907 0.407839 0.238094 0.047 Uiso 1 1 calc R U . . .
C33 C 0.2773(2) 0.33804(11) 0.33293(17) 0.0272(5) Uani 1 1 d . . . . .
C34 C 0.4082(2) 0.35669(11) 0.36682(18) 0.0284(5) Uani 1 1 d . . . . .
H34A H 0.438620 0.392777 0.342675 0.034 Uiso 1 1 calc R U . . .
B1 B 0.7171(2) 0.32973(12) 0.41155(19) 0.0224(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.732(2) . ?
Cl2 C5 1.726(2) . ?
Cl3 C12 1.727(2) . ?
Cl4 C13 1.728(2) . ?
Cl5 C20 1.727(2) . ?
Cl6 C21 1.727(2) . ?
O1 C25 1.383(3) . ?
O1 B1 1.434(3) . ?
N1 C1 1.364(3) . ?
N1 C8 1.372(3) . ?
N1 B1 1.500(3) . ?
N2 C8 1.337(3) . ?
N2 C9 1.346(3) . ?
N3 C9 1.367(3) . ?
N3 C16 1.368(3) . ?
N3 B1 1.501(3) . ?
N4 C17 1.338(3) . ?
N4 C16 1.352(3) . ?
N5 C24 1.359(3) . ?
N5 C17 1.368(3) . ?
N5 B1 1.494(3) . ?
N6 C1 1.343(3) . ?
N6 C24 1.344(3) . ?
C1 C2 1.453(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.409(3) . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.404(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.394(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.452(3) . ?
C9 C10 1.442(3) . ?
C10 C11 1.389(3) . ?
C10 C15 1.424(3) . ?
C11 C12 1.373(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.412(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.389(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.455(3) . ?
C17 C18 1.464(3) . ?
C18 C19 1.391(3) . ?
C18 C23 1.421(3) . ?
C19 C20 1.384(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.409(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.384(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.454(3) . ?
C25 C34 1.350(3) . ?
C25 C26 1.418(3) . ?
C26 C27 1.362(3) . ?
C26 H26A 0.9500 . ?
C27 C28 1.409(3) . ?
C27 H27A 0.9500 . ?
C28 C33 1.411(3) . ?
C28 C29 1.435(3) . ?
C29 C30 1.350(4) . ?
C29 H29A 0.9500 . ?
C30 C31 1.404(4) . ?
C30 H30A 0.9500 . ?
C31 C32 1.369(4) . ?
C31 H31A 0.9500 . ?
C32 C33 1.405(3) . ?
C32 H32A 0.9500 . ?
C33 C34 1.436(3) . ?
C34 H34A 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
C25 O1 B1 120.26(17) . . ?
C1 N1 C8 112.45(17) . . ?
C1 N1 B1 122.90(18) . . ?
C8 N1 B1 122.52(19) . . ?
C8 N2 C9 116.50(19) . . ?
C9 N3 C16 112.84(18) . . ?
C9 N3 B1 122.26(18) . . ?
C16 N3 B1 123.22(18) . . ?
C17 N4 C16 116.97(18) . . ?
C24 N5 C17 113.42(18) . . ?
C24 N5 B1 122.66(18) . . ?
C17 N5 B1 123.48(19) . . ?
C1 N6 C24 116.65(19) . . ?
N6 C1 N1 123.10(18) . . ?
N6 C1 C2 129.7(2) . . ?
N1 C1 C2 105.93(18) . . ?
C3 C2 C7 120.8(2) . . ?
C3 C2 C1 131.3(2) . . ?
C7 C2 C1 107.38(18) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3A 121.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 Cl1 118.94(18) . . ?
C5 C4 Cl1 119.88(16) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 Cl2 118.24(18) . . ?
C4 C5 Cl2 120.55(17) . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 H6A 121.1 . . ?
C7 C6 H6A 121.1 . . ?
C6 C7 C2 120.8(2) . . ?
C6 C7 C8 131.4(2) . . ?
C2 C7 C8 107.25(18) . . ?
N2 C8 N1 123.08(19) . . ?
N2 C8 C7 128.7(2) . . ?
N1 C8 C7 105.75(19) . . ?
N2 C9 N3 123.3(2) . . ?
N2 C9 C10 128.0(2) . . ?
N3 C9 C10 106.23(18) . . ?
C11 C10 C15 121.1(2) . . ?
C11 C10 C9 131.5(2) . . ?
C15 C10 C9 107.19(19) . . ?
C12 C11 C10 118.0(2) . . ?
C12 C11 H11A 121.0 . . ?
C10 C11 H11A 121.0 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 Cl3 118.74(18) . . ?
C13 C12 Cl3 120.11(18) . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 Cl4 118.50(17) . . ?
C12 C13 Cl4 120.02(18) . . ?
C13 C14 C15 118.2(2) . . ?
C13 C14 H14A 120.9 . . ?
C15 C14 H14A 120.9 . . ?
C14 C15 C10 120.1(2) . . ?
C14 C15 C16 132.6(2) . . ?
C10 C15 C16 107.12(18) . . ?
N4 C16 N3 122.8(2) . . ?
N4 C16 C15 129.91(19) . . ?
N3 C16 C15 105.58(18) . . ?
N4 C17 N5 122.1(2) . . ?
N4 C17 C18 131.4(2) . . ?
N5 C17 C18 104.92(18) . . ?
C19 C18 C23 119.9(2) . . ?
C19 C18 C17 132.9(2) . . ?
C23 C18 C17 107.16(18) . . ?
C20 C19 C18 118.4(2) . . ?
C20 C19 H19A 120.8 . . ?
C18 C19 H19A 120.8 . . ?
C19 C20 C21 121.3(2) . . ?
C19 C20 Cl5 118.53(18) . . ?
C21 C20 Cl5 120.13(18) . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 Cl6 118.36(18) . . ?
C20 C21 Cl6 120.89(18) . . ?
C23 C22 C21 118.3(2) . . ?
C23 C22 H22A 120.9 . . ?
C21 C22 H22A 120.9 . . ?
C22 C23 C18 121.3(2) . . ?
C22 C23 C24 131.6(2) . . ?
C18 C23 C24 107.04(19) . . ?
N6 C24 N5 122.5(2) . . ?
N6 C24 C23 130.2(2) . . ?
N5 C24 C23 105.68(18) . . ?
C34 C25 O1 121.3(2) . . ?
C34 C25 C26 121.0(2) . . ?
O1 C25 C26 117.6(2) . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26A 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C26 C27 C28 120.6(2) . . ?
C26 C27 H27A 119.7 . . ?
C28 C27 H27A 119.7 . . ?
C27 C28 C33 119.7(2) . . ?
C27 C28 C29 122.1(2) . . ?
C33 C28 C29 118.2(2) . . ?
C30 C29 C28 120.7(3) . . ?
C30 C29 H29A 119.6 . . ?
C28 C29 H29A 119.6 . . ?
C29 C30 C31 120.5(2) . . ?
C29 C30 H30A 119.7 . . ?
C31 C30 H30A 119.7 . . ?
C32 C31 C30 120.5(3) . . ?
C32 C31 H31A 119.7 . . ?
C30 C31 H31A 119.7 . . ?
C31 C32 C33 120.3(3) . . ?
C31 C32 H32A 119.8 . . ?
C33 C32 H32A 119.8 . . ?
C32 C33 C28 119.8(2) . . ?
C32 C33 C34 121.7(2) . . ?
C28 C33 C34 118.5(2) . . ?
C25 C34 C33 120.1(2) . . ?
C25 C34 H34A 120.0 . . ?
C33 C34 H34A 120.0 . . ?
O1 B1 N5 116.21(19) . . ?
O1 B1 N1 111.15(18) . . ?
N5 B1 N1 103.92(18) . . ?
O1 B1 N3 116.6(2) . . ?
N5 B1 N3 103.31(18) . . ?
N1 B1 N3 104.21(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
C24 N6 C1 N1 -11.3(3) . . . . ?
C24 N6 C1 C2 153.7(2) . . . . ?
C8 N1 C1 N6 157.3(2) . . . . ?
B1 N1 C1 N6 -6.4(3) . . . . ?
C8 N1 C1 C2 -10.8(2) . . . . ?
B1 N1 C1 C2 -174.54(19) . . . . ?
N6 C1 C2 C3 9.7(4) . . . . ?
N1 C1 C2 C3 176.7(2) . . . . ?
N6 C1 C2 C7 -161.6(2) . . . . ?
N1 C1 C2 C7 5.5(2) . . . . ?
C7 C2 C3 C4 -2.0(3) . . . . ?
C1 C2 C3 C4 -172.3(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C2 C3 C4 Cl1 178.14(16) . . . . ?
C3 C4 C5 C6 2.6(3) . . . . ?
Cl1 C4 C5 C6 -175.68(17) . . . . ?
C3 C4 C5 Cl2 -178.06(17) . . . . ?
Cl1 C4 C5 Cl2 3.7(3) . . . . ?
C4 C5 C6 C7 -2.8(3) . . . . ?
Cl2 C5 C6 C7 177.86(17) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C5 C6 C7 C8 171.5(2) . . . . ?
C3 C2 C7 C6 1.7(3) . . . . ?
C1 C2 C7 C6 174.1(2) . . . . ?
C3 C2 C7 C8 -171.11(19) . . . . ?
C1 C2 C7 C8 1.3(2) . . . . ?
C9 N2 C8 N1 10.1(3) . . . . ?
C9 N2 C8 C7 -149.6(2) . . . . ?
C1 N1 C8 N2 -152.1(2) . . . . ?
B1 N1 C8 N2 11.7(3) . . . . ?
C1 N1 C8 C7 11.5(2) . . . . ?
B1 N1 C8 C7 175.38(19) . . . . ?
C6 C7 C8 N2 -16.9(4) . . . . ?
C2 C7 C8 N2 154.9(2) . . . . ?
C6 C7 C8 N1 -179.3(2) . . . . ?
C2 C7 C8 N1 -7.5(2) . . . . ?
C8 N2 C9 N3 -9.8(3) . . . . ?
C8 N2 C9 C10 150.0(2) . . . . ?
C16 N3 C9 N2 153.4(2) . . . . ?
B1 N3 C9 N2 -12.3(3) . . . . ?
C16 N3 C9 C10 -10.2(2) . . . . ?
B1 N3 C9 C10 -175.85(18) . . . . ?
N2 C9 C10 C11 17.0(4) . . . . ?
N3 C9 C10 C11 179.5(2) . . . . ?
N2 C9 C10 C15 -157.0(2) . . . . ?
N3 C9 C10 C15 5.5(2) . . . . ?
C15 C10 C11 C12 -2.9(3) . . . . ?
C9 C10 C11 C12 -176.2(2) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C10 C11 C12 Cl3 -176.79(17) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
Cl3 C12 C13 C14 179.12(17) . . . . ?
C11 C12 C13 Cl4 -175.53(17) . . . . ?
Cl3 C12 C13 Cl4 3.0(3) . . . . ?
C12 C13 C14 C15 -1.8(3) . . . . ?
Cl4 C13 C14 C15 174.44(16) . . . . ?
C13 C14 C15 C10 0.6(3) . . . . ?
C13 C14 C15 C16 175.4(2) . . . . ?
C11 C10 C15 C14 1.8(3) . . . . ?
C9 C10 C15 C14 176.55(19) . . . . ?
C11 C10 C15 C16 -174.2(2) . . . . ?
C9 C10 C15 C16 0.6(2) . . . . ?
C17 N4 C16 N3 8.9(3) . . . . ?
C17 N4 C16 C15 -153.9(2) . . . . ?
C9 N3 C16 N4 -155.9(2) . . . . ?
B1 N3 C16 N4 9.6(3) . . . . ?
C9 N3 C16 C15 10.5(2) . . . . ?
B1 N3 C16 C15 175.97(18) . . . . ?
C14 C15 C16 N4 -16.6(4) . . . . ?
C10 C15 C16 N4 158.7(2) . . . . ?
C14 C15 C16 N3 178.3(2) . . . . ?
C10 C15 C16 N3 -6.4(2) . . . . ?
C16 N4 C17 N5 -4.5(3) . . . . ?
C16 N4 C17 C18 158.8(2) . . . . ?
C24 N5 C17 N4 153.8(2) . . . . ?
B1 N5 C17 N4 -18.7(3) . . . . ?
C24 N5 C17 C18 -13.3(2) . . . . ?
B1 N5 C17 C18 174.19(18) . . . . ?
N4 C17 C18 C19 21.6(4) . . . . ?
N5 C17 C18 C19 -172.9(2) . . . . ?
N4 C17 C18 C23 -158.3(2) . . . . ?
N5 C17 C18 C23 7.2(2) . . . . ?
C23 C18 C19 C20 -1.3(3) . . . . ?
C17 C18 C19 C20 178.8(2) . . . . ?
C18 C19 C20 C21 1.6(3) . . . . ?
C18 C19 C20 Cl5 -176.33(16) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
Cl5 C20 C21 C22 177.47(17) . . . . ?
C19 C20 C21 Cl6 -178.02(16) . . . . ?
Cl5 C20 C21 Cl6 -0.1(3) . . . . ?
C20 C21 C22 C23 -1.0(3) . . . . ?
Cl6 C21 C22 C23 176.65(16) . . . . ?
C21 C22 C23 C18 1.2(3) . . . . ?
C21 C22 C23 C24 -179.8(2) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
C17 C18 C23 C22 179.83(19) . . . . ?
C19 C18 C23 C24 -179.25(19) . . . . ?
C17 C18 C23 C24 0.7(2) . . . . ?
C1 N6 C24 N5 5.0(3) . . . . ?
C1 N6 C24 C23 -158.5(2) . . . . ?
C17 N5 C24 N6 -153.2(2) . . . . ?
B1 N5 C24 N6 19.4(3) . . . . ?
C17 N5 C24 C23 13.8(2) . . . . ?
B1 N5 C24 C23 -173.62(18) . . . . ?
C22 C23 C24 N6 -21.8(4) . . . . ?
C18 C23 C24 N6 157.3(2) . . . . ?
C22 C23 C24 N5 172.6(2) . . . . ?
C18 C23 C24 N5 -8.3(2) . . . . ?
B1 O1 C25 C34 -85.5(3) . . . . ?
B1 O1 C25 C26 98.0(3) . . . . ?
C34 C25 C26 C27 0.7(4) . . . . ?
O1 C25 C26 C27 177.2(2) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C33 -0.7(4) . . . . ?
C26 C27 C28 C29 179.3(2) . . . . ?
C27 C28 C29 C30 -179.9(2) . . . . ?
C33 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 -0.3(4) . . . . ?
C29 C30 C31 C32 0.1(4) . . . . ?
C30 C31 C32 C33 0.2(4) . . . . ?
C31 C32 C33 C28 -0.4(4) . . . . ?
C31 C32 C33 C34 179.5(2) . . . . ?
C27 C28 C33 C32 -179.8(2) . . . . ?
C29 C28 C33 C32 0.2(3) . . . . ?
C27 C28 C33 C34 0.3(3) . . . . ?
C29 C28 C33 C34 -179.7(2) . . . . ?
O1 C25 C34 C33 -177.46(19) . . . . ?
C26 C25 C34 C33 -1.0(3) . . . . ?
C32 C33 C34 C25 -179.4(2) . . . . ?
C28 C33 C34 C25 0.5(3) . . . . ?
C25 O1 B1 N5 69.5(3) . . . . ?
C25 O1 B1 N1 -171.98(19) . . . . ?
C25 O1 B1 N3 -52.8(3) . . . . ?
C24 N5 B1 O1 90.6(2) . . . . ?
C17 N5 B1 O1 -97.6(2) . . . . ?
C24 N5 B1 N1 -31.8(3) . . . . ?
C17 N5 B1 N1 140.02(19) . . . . ?
C24 N5 B1 N3 -140.36(19) . . . . ?
C17 N5 B1 N3 31.4(3) . . . . ?
C1 N1 B1 O1 -100.2(2) . . . . ?
C8 N1 B1 O1 97.7(2) . . . . ?
C1 N1 B1 N5 25.6(3) . . . . ?
C8 N1 B1 N5 -136.60(19) . . . . ?
C1 N1 B1 N3 133.5(2) . . . . ?
C8 N1 B1 N3 -28.7(3) . . . . ?
C9 N3 B1 O1 -94.0(2) . . . . ?
C16 N3 B1 O1 101.8(2) . . . . ?
C9 N3 B1 N5 137.24(19) . . . . ?
C16 N3 B1 N5 -26.9(3) . . . . ?
C9 N3 B1 N1 28.9(3) . . . . ?
C16 N3 B1 N1 -135.26(19) . . . . ?

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.063



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichlorobenzene/dimethoxybezene/heptane'
####################################################################### 
# 
# 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_d19138_a
_database_code_depnum_ccdc_archive 'CCDC 2087100'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Cl-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H6 B Cl7 N6'
_chemical_formula_sum            'C24 H6 B Cl7 N6'
_chemical_formula_weight         637.31

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0845(8)
_cell_length_b                   7.4155(4)
_cell_length_c                   25.4585(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.476(2)
_cell_angle_gamma                90
_cell_volume                     2436.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5690
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.30

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.845
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6945
_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                   '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            34990
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.622
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5610
_reflns_number_gt                4007
_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 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)+(0.0301P)²+1.4264P] 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         5610
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
Cl1 Cl 0.61260(5) -0.25207(8) 0.33887(2) 0.02217(14) Uani 1 1 d . . . . .
Cl2 Cl 0.35682(5) 0.78045(10) 0.40920(3) 0.0434(2) Uani 1 1 d . . . . .
Cl3 Cl 0.56247(5) 0.78120(8) 0.49196(3) 0.02825(15) Uani 1 1 d . . . . .
Cl4 Cl 1.20615(5) 0.27827(10) 0.40998(3) 0.03228(17) Uani 1 1 d . . . . .
Cl5 Cl 1.20985(5) 0.16568(10) 0.29146(3) 0.03563(18) Uani 1 1 d . . . . .
Cl6 Cl 0.60103(5) 0.18435(10) 0.02426(2) 0.03462(17) Uani 1 1 d . . . . .
Cl7 Cl 0.37787(5) 0.29256(9) 0.04364(2) 0.02908(16) Uani 1 1 d . . . . .
N1 N 0.60300(14) 0.1210(2) 0.34804(7) 0.0154(4) Uani 1 1 d . . . . .
N2 N 0.76196(14) 0.1841(3) 0.40506(7) 0.0177(4) Uani 1 1 d . . . . .
N3 N 0.75977(14) 0.0101(2) 0.32666(7) 0.0150(4) Uani 1 1 d . . . . .
N4 N 0.77375(13) -0.0289(2) 0.23544(7) 0.0147(4) Uani 1 1 d . . . . .
N5 N 0.60907(14) 0.0134(2) 0.26172(7) 0.0150(4) Uani 1 1 d . . . . .
N6 N 0.46578(14) 0.1916(2) 0.27729(8) 0.0167(4) Uani 1 1 d . . . . .
C1 C 0.51265(16) 0.2089(3) 0.32817(9) 0.0163(5) Uani 1 1 d . . . . .
C2 C 0.50008(17) 0.3456(3) 0.36790(9) 0.0163(5) Uani 1 1 d . . . . .
C3 C 0.42589(17) 0.4785(3) 0.36934(10) 0.0201(5) Uani 1 1 d . . . . .
H3A H 0.364018 0.480632 0.343896 0.024 Uiso 1 1 calc R U . . .
C4 C 0.44473(18) 0.6075(3) 0.40886(10) 0.0224(5) Uani 1 1 d . . . . .
C5 C 0.53652(18) 0.6071(3) 0.44659(9) 0.0196(5) Uani 1 1 d . . . . .
C6 C 0.60996(18) 0.4743(3) 0.44602(9) 0.0188(5) Uani 1 1 d . . . . .
H6A H 0.671286 0.472402 0.471838 0.023 Uiso 1 1 calc R U . . .
C7 C 0.59180(17) 0.3437(3) 0.40673(9) 0.0174(5) Uani 1 1 d . . . . .
C8 C 0.65888(17) 0.2042(3) 0.39118(9) 0.0163(5) Uani 1 1 d . . . . .
C9 C 0.81080(17) 0.0973(3) 0.37054(9) 0.0158(5) Uani 1 1 d . . . . .
C10 C 0.91756(17) 0.1119(3) 0.36170(9) 0.0160(5) Uani 1 1 d . . . . .
C11 C 1.00535(17) 0.1846(3) 0.39301(9) 0.0184(5) Uani 1 1 d . . . . .
H11A H 1.003695 0.224395 0.428323 0.022 Uiso 1 1 calc R U . . .
C12 C 1.09502(17) 0.1968(3) 0.37097(9) 0.0200(5) Uani 1 1 d . . . . .
C13 C 1.09714(17) 0.1439(3) 0.31829(10) 0.0209(5) Uani 1 1 d . . . . .
C14 C 1.01016(17) 0.0732(3) 0.28674(9) 0.0179(5) Uani 1 1 d . . . . .
H14A H 1.011407 0.039691 0.250836 0.021 Uiso 1 1 calc R U . . .
C15 C 0.92117(17) 0.0527(3) 0.30908(9) 0.0158(5) Uani 1 1 d . . . . .
C16 C 0.81691(17) -0.0050(3) 0.28642(9) 0.0159(5) Uani 1 1 d . . . . .
C17 C 0.67030(17) -0.0047(3) 0.22397(9) 0.0142(5) Uani 1 1 d . . . . .
C18 C 0.60823(17) 0.0527(3) 0.17452(9) 0.0161(5) Uani 1 1 d . . . . .
C19 C 0.63571(17) 0.0733(3) 0.12472(9) 0.0174(5) Uani 1 1 d . . . . .
H19A H 0.701639 0.035783 0.117813 0.021 Uiso 1 1 calc R U . . .
C20 C 0.56384(18) 0.1503(3) 0.08546(9) 0.0196(5) Uani 1 1 d . . . . .
C21 C 0.46563(17) 0.2031(3) 0.09541(9) 0.0194(5) Uani 1 1 d . . . . .
C22 C 0.43924(17) 0.1888(3) 0.14563(9) 0.0183(5) Uani 1 1 d . . . . .
H22A H 0.373463 0.228023 0.152309 0.022 Uiso 1 1 calc R U . . .
C23 C 0.51197(17) 0.1150(3) 0.18632(9) 0.0155(5) Uani 1 1 d . . . . .
C24 C 0.51794(17) 0.1026(3) 0.24396(9) 0.0159(5) Uani 1 1 d . . . . .
B1 B 0.64599(19) -0.0243(3) 0.31877(10) 0.0157(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.838(3) . ?
Cl2 C4 1.724(2) . ?
Cl3 C5 1.728(2) . ?
Cl4 C12 1.729(2) . ?
Cl5 C13 1.732(2) . ?
Cl6 C20 1.725(2) . ?
Cl7 C21 1.731(2) . ?
N1 C8 1.363(3) . ?
N1 C1 1.372(3) . ?
N1 B1 1.473(3) . ?
N2 C9 1.334(3) . ?
N2 C8 1.345(3) . ?
N3 C9 1.366(3) . ?
N3 C16 1.369(3) . ?
N3 B1 1.491(3) . ?
N4 C16 1.339(3) . ?
N4 C17 1.349(3) . ?
N5 C17 1.355(3) . ?
N5 C24 1.373(3) . ?
N5 B1 1.480(3) . ?
N6 C1 1.345(3) . ?
N6 C24 1.346(3) . ?
C1 C2 1.461(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.424(3) . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.409(3) . ?
C5 C6 1.378(3) . ?
C6 C7 1.384(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.453(3) . ?
C9 C10 1.455(3) . ?
C10 C11 1.394(3) . ?
C10 C15 1.418(3) . ?
C11 C12 1.384(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.402(3) . ?
C13 C14 1.384(3) . ?
C14 C15 1.386(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.455(3) . ?
C17 C18 1.445(3) . ?
C18 C19 1.382(3) . ?
C18 C23 1.419(3) . ?
C19 C20 1.379(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.406(3) . ?
C21 C22 1.382(3) . ?
C22 C23 1.398(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.460(3) . ?

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
C8 N1 C1 113.41(19) . . ?
C8 N1 B1 122.68(19) . . ?
C1 N1 B1 122.60(19) . . ?
C9 N2 C8 116.66(19) . . ?
C9 N3 C16 113.40(19) . . ?
C9 N3 B1 122.3(2) . . ?
C16 N3 B1 122.79(19) . . ?
C16 N4 C17 116.13(19) . . ?
C17 N5 C24 113.38(19) . . ?
C17 N5 B1 122.80(19) . . ?
C24 N5 B1 122.65(19) . . ?
C1 N6 C24 117.11(19) . . ?
N6 C1 N1 122.6(2) . . ?
N6 C1 C2 130.4(2) . . ?
N1 C1 C2 105.25(18) . . ?
C3 C2 C7 120.1(2) . . ?
C3 C2 C1 132.1(2) . . ?
C7 C2 C1 107.21(19) . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3A 121.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 Cl2 118.68(19) . . ?
C5 C4 Cl2 119.51(19) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 Cl3 118.71(18) . . ?
C4 C5 Cl3 120.39(18) . . ?
C5 C6 C7 118.1(2) . . ?
C5 C6 H6A 121.0 . . ?
C7 C6 H6A 121.0 . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 C8 130.9(2) . . ?
C2 C7 C8 107.2(2) . . ?
N2 C8 N1 122.9(2) . . ?
N2 C8 C7 129.2(2) . . ?
N1 C8 C7 105.90(18) . . ?
N2 C9 N3 123.0(2) . . ?
N2 C9 C10 130.0(2) . . ?
N3 C9 C10 105.1(2) . . ?
C11 C10 C15 120.5(2) . . ?
C11 C10 C9 131.5(2) . . ?
C15 C10 C9 107.77(19) . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11A 121.1 . . ?
C10 C11 H11A 121.1 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 Cl4 118.61(18) . . ?
C13 C12 Cl4 119.99(18) . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 Cl5 118.60(19) . . ?
C12 C13 Cl5 120.24(17) . . ?
C13 C14 C15 118.0(2) . . ?
C13 C14 H14A 121.0 . . ?
C15 C14 H14A 121.0 . . ?
C14 C15 C10 121.0(2) . . ?
C14 C15 C16 131.7(2) . . ?
C10 C15 C16 106.9(2) . . ?
N4 C16 N3 122.8(2) . . ?
N4 C16 C15 129.9(2) . . ?
N3 C16 C15 105.73(19) . . ?
N4 C17 N5 123.28(19) . . ?
N4 C17 C18 128.9(2) . . ?
N5 C17 C18 105.99(19) . . ?
C19 C18 C23 122.1(2) . . ?
C19 C18 C17 129.6(2) . . ?
C23 C18 C17 107.6(2) . . ?
C20 C19 C18 117.5(2) . . ?
C20 C19 H19A 121.3 . . ?
C18 C19 H19A 121.3 . . ?
C19 C20 C21 121.3(2) . . ?
C19 C20 Cl6 117.08(18) . . ?
C21 C20 Cl6 121.61(18) . . ?
C22 C21 C20 121.4(2) . . ?
C22 C21 Cl7 119.88(18) . . ?
C20 C21 Cl7 118.75(18) . . ?
C21 C22 C23 118.2(2) . . ?
C21 C22 H22A 120.9 . . ?
C23 C22 H22A 120.9 . . ?
C22 C23 C18 119.4(2) . . ?
C22 C23 C24 133.4(2) . . ?
C18 C23 C24 106.84(19) . . ?
N6 C24 N5 122.1(2) . . ?
N6 C24 C23 130.8(2) . . ?
N5 C24 C23 105.14(19) . . ?
N1 B1 N5 105.54(19) . . ?
N1 B1 N3 105.21(19) . . ?
N5 B1 N3 104.90(19) . . ?
N1 B1 Cl1 113.78(17) . . ?
N5 B1 Cl1 113.13(16) . . ?
N3 B1 Cl1 113.44(16) . . ?

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 -8.6(3) . . . . ?
C24 N6 C1 C2 153.8(2) . . . . ?
C8 N1 C1 N6 155.6(2) . . . . ?
B1 N1 C1 N6 -11.6(3) . . . . ?
C8 N1 C1 C2 -10.5(2) . . . . ?
B1 N1 C1 C2 -177.8(2) . . . . ?
N6 C1 C2 C3 13.0(4) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
N6 C1 C2 C7 -158.0(2) . . . . ?
N1 C1 C2 C7 6.7(2) . . . . ?
C7 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C4 -169.4(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 Cl2 176.61(18) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
Cl2 C4 C5 C6 -177.57(19) . . . . ?
C3 C4 C5 Cl3 174.51(19) . . . . ?
Cl2 C4 C5 Cl3 -1.5(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
Cl3 C5 C6 C7 -174.90(18) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C5 C6 C7 C8 170.3(2) . . . . ?
C3 C2 C7 C6 -1.0(3) . . . . ?
C1 C2 C7 C6 171.3(2) . . . . ?
C3 C2 C7 C8 -173.3(2) . . . . ?
C1 C2 C7 C8 -1.0(3) . . . . ?
C9 N2 C8 N1 8.8(3) . . . . ?
C9 N2 C8 C7 -152.7(2) . . . . ?
C1 N1 C8 N2 -155.2(2) . . . . ?
B1 N1 C8 N2 12.0(3) . . . . ?
C1 N1 C8 C7 9.9(3) . . . . ?
B1 N1 C8 C7 177.2(2) . . . . ?
C6 C7 C8 N2 -12.5(4) . . . . ?
C2 C7 C8 N2 158.9(2) . . . . ?
C6 C7 C8 N1 -176.4(2) . . . . ?
C2 C7 C8 N1 -5.0(2) . . . . ?
C8 N2 C9 N3 -8.9(3) . . . . ?
C8 N2 C9 C10 152.9(2) . . . . ?
C16 N3 C9 N2 154.7(2) . . . . ?
B1 N3 C9 N2 -11.4(3) . . . . ?
C16 N3 C9 C10 -10.9(2) . . . . ?
B1 N3 C9 C10 -177.04(19) . . . . ?
N2 C9 C10 C11 17.1(4) . . . . ?
N3 C9 C10 C11 -178.7(2) . . . . ?
N2 C9 C10 C15 -156.6(2) . . . . ?
N3 C9 C10 C15 7.6(2) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?
C9 C10 C11 C12 -172.9(2) . . . . ?
C10 C11 C12 C13 2.2(3) . . . . ?
C10 C11 C12 Cl4 -177.51(17) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
Cl4 C12 C13 C14 178.02(18) . . . . ?
C11 C12 C13 Cl5 178.55(19) . . . . ?
Cl4 C12 C13 Cl5 -1.8(3) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
Cl5 C13 C14 C15 178.55(17) . . . . ?
C13 C14 C15 C10 3.5(3) . . . . ?
C13 C14 C15 C16 175.4(2) . . . . ?
C11 C10 C15 C14 -3.0(3) . . . . ?
C9 C10 C15 C14 171.5(2) . . . . ?
C11 C10 C15 C16 -176.7(2) . . . . ?
C9 C10 C15 C16 -2.2(2) . . . . ?
C17 N4 C16 N3 11.7(3) . . . . ?
C17 N4 C16 C15 -151.6(2) . . . . ?
C9 N3 C16 N4 -157.2(2) . . . . ?
B1 N3 C16 N4 8.9(3) . . . . ?
C9 N3 C16 C15 9.6(2) . . . . ?
B1 N3 C16 C15 175.68(19) . . . . ?
C14 C15 C16 N4 -11.3(4) . . . . ?
C10 C15 C16 N4 161.4(2) . . . . ?
C14 C15 C16 N3 -176.8(2) . . . . ?
C10 C15 C16 N3 -4.1(2) . . . . ?
C16 N4 C17 N5 -10.6(3) . . . . ?
C16 N4 C17 C18 151.7(2) . . . . ?
C24 N5 C17 N4 156.5(2) . . . . ?
B1 N5 C17 N4 -11.4(3) . . . . ?
C24 N5 C17 C18 -9.3(2) . . . . ?
B1 N5 C17 C18 -177.20(19) . . . . ?
N4 C17 C18 C19 10.1(4) . . . . ?
N5 C17 C18 C19 174.7(2) . . . . ?
N4 C17 C18 C23 -160.9(2) . . . . ?
N5 C17 C18 C23 3.7(2) . . . . ?
C23 C18 C19 C20 -2.8(3) . . . . ?
C17 C18 C19 C20 -172.7(2) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C18 C19 C20 Cl6 177.26(18) . . . . ?
C19 C20 C21 C22 3.5(4) . . . . ?
Cl6 C20 C21 C22 -174.76(18) . . . . ?
C19 C20 C21 Cl7 -178.02(18) . . . . ?
Cl6 C20 C21 Cl7 3.7(3) . . . . ?
C20 C21 C22 C23 -1.9(3) . . . . ?
Cl7 C21 C22 C23 179.67(16) . . . . ?
C21 C22 C23 C18 -1.9(3) . . . . ?
C21 C22 C23 C24 169.7(2) . . . . ?
C19 C18 C23 C22 4.4(3) . . . . ?
C17 C18 C23 C22 176.23(19) . . . . ?
C19 C18 C23 C24 -169.3(2) . . . . ?
C17 C18 C23 C24 2.5(2) . . . . ?
C1 N6 C24 N5 7.9(3) . . . . ?
C1 N6 C24 C23 -153.9(2) . . . . ?
C17 N5 C24 N6 -155.0(2) . . . . ?
B1 N5 C24 N6 12.9(3) . . . . ?
C17 N5 C24 C23 10.8(2) . . . . ?
B1 N5 C24 C23 178.73(19) . . . . ?
C22 C23 C24 N6 -16.1(4) . . . . ?
C18 C23 C24 N6 156.3(2) . . . . ?
C22 C23 C24 N5 179.8(2) . . . . ?
C18 C23 C24 N5 -7.8(2) . . . . ?
C8 N1 B1 N5 -138.3(2) . . . . ?
C1 N1 B1 N5 27.7(3) . . . . ?
C8 N1 B1 N3 -27.7(3) . . . . ?
C1 N1 B1 N3 138.4(2) . . . . ?
C8 N1 B1 Cl1 97.1(2) . . . . ?
C1 N1 B1 Cl1 -96.9(2) . . . . ?
C17 N5 B1 N1 138.4(2) . . . . ?
C24 N5 B1 N1 -28.4(3) . . . . ?
C17 N5 B1 N3 27.5(3) . . . . ?
C24 N5 B1 N3 -139.3(2) . . . . ?
C17 N5 B1 Cl1 -96.6(2) . . . . ?
C24 N5 B1 Cl1 96.6(2) . . . . ?
C9 N3 B1 N1 27.5(3) . . . . ?
C16 N3 B1 N1 -137.4(2) . . . . ?
C9 N3 B1 N5 138.5(2) . . . . ?
C16 N3 B1 N5 -26.3(3) . . . . ?
C9 N3 B1 Cl1 -97.5(2) . . . . ?
C16 N3 B1 Cl1 97.6(2) . . . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.072



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chlorobenzene/heptane'
####################################################################### 
# 
# 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_d19232a_a
_database_code_depnum_ccdc_archive 'CCDC 2087106'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        IPhO-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H10 B Cl6 I N6 O'
_chemical_formula_sum            'C30 H10 B Cl6 I N6 O'
_chemical_formula_weight         820.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.8551(3)
_cell_length_b                   15.1122(3)
_cell_length_c                   23.9203(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5731.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9613
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.46

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_F_000             3200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.718
_shelx_estimated_absorpt_T_min   0.585
_shelx_estimated_absorpt_T_max   0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6732
_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 PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            130895
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             13117
_reflns_number_gt                12227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_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 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)+(0.0362P)²+5.4662P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     diff
_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_abs_structure_details 
; 
 Flack x determined using 5645 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.015(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         13117
_refine_ls_number_parameters     811
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
I1A I 0.29730(2) 0.40445(2) 0.46145(2) 0.02478(7) Uani 1 1 d . . . . .
Cl1A Cl 0.92530(7) 0.00204(7) 0.70236(5) 0.0235(2) Uani 1 1 d . . . . .
Cl2A Cl 0.85889(8) 0.05216(9) 0.82086(5) 0.0296(3) Uani 1 1 d . . . . .
Cl3A Cl 0.23292(9) 0.15790(9) 0.89016(5) 0.0339(3) Uani 1 1 d . . . . .
Cl4A Cl 0.10647(8) 0.11338(9) 0.79212(6) 0.0334(3) Uani 1 1 d . . . . .
Cl5A Cl 0.29125(8) -0.08188(9) 0.42323(5) 0.0344(3) Uani 1 1 d . . . . .
Cl6A Cl 0.47993(8) -0.09602(8) 0.38505(5) 0.0285(2) Uani 1 1 d . . . . .
O1A O 0.53642(19) 0.3158(2) 0.61600(13) 0.0194(6) Uani 1 1 d . . . . .
N1A N 0.5817(2) 0.1823(2) 0.65798(15) 0.0159(7) Uani 1 1 d . . . . .
N2A N 0.5314(2) 0.2010(2) 0.75082(15) 0.0176(7) Uani 1 1 d . . . . .
N3A N 0.4388(2) 0.2205(2) 0.67279(15) 0.0166(7) Uani 1 1 d . . . . .
N4A N 0.3393(2) 0.1587(2) 0.60927(15) 0.0178(7) Uani 1 1 d . . . . .
N5A N 0.4841(2) 0.1655(2) 0.58522(15) 0.0156(7) Uani 1 1 d . . . . .
N6A N 0.6208(2) 0.1021(2) 0.57663(15) 0.0170(7) Uani 1 1 d . . . . .
C1A C 0.6370(3) 0.1314(3) 0.62831(18) 0.0175(8) Uani 1 1 d . . . . .
C2A C 0.7010(3) 0.1053(3) 0.6686(2) 0.0179(9) Uani 1 1 d . . . . .
C3A C 0.7765(3) 0.0595(3) 0.66268(19) 0.0173(8) Uani 1 1 d . . . . .
H3AA H 0.793900 0.037512 0.627322 0.021 Uiso 1 1 calc R U . . .
C4A C 0.8255(3) 0.0471(3) 0.7099(2) 0.0185(8) Uani 1 1 d . . . . .
C5A C 0.7967(3) 0.0720(3) 0.7629(2) 0.0198(9) Uani 1 1 d . . . . .
C6A C 0.7193(3) 0.1143(3) 0.76999(19) 0.0201(9) Uani 1 1 d . . . . .
H6AA H 0.698937 0.129413 0.806114 0.024 Uiso 1 1 calc R U . . .
C7A C 0.6730(3) 0.1334(3) 0.72229(18) 0.0177(8) Uani 1 1 d . . . . .
C8A C 0.5925(3) 0.1794(3) 0.71462(18) 0.0166(8) Uani 1 1 d . . . . .
C9A C 0.4542(3) 0.2157(3) 0.72903(17) 0.0180(8) Uani 1 1 d . . . . .
C10A C 0.3713(3) 0.2022(3) 0.75518(18) 0.0175(8) Uani 1 1 d . . . . .
C11A C 0.3477(3) 0.1929(3) 0.81061(18) 0.0205(9) Uani 1 1 d . . . . .
H11A H 0.386609 0.202922 0.840151 0.025 Uiso 1 1 calc R U . . .
C12A C 0.2642(3) 0.1682(3) 0.8213(2) 0.0226(9) Uani 1 1 d . . . . .
C13A C 0.2081(3) 0.1506(3) 0.7778(2) 0.0228(10) Uani 1 1 d . . . . .
C14A C 0.2306(3) 0.1603(3) 0.7224(2) 0.0218(10) Uani 1 1 d . . . . .
H14A H 0.191687 0.148849 0.693058 0.026 Uiso 1 1 calc R U . . .
C15A C 0.3135(3) 0.1879(3) 0.71129(19) 0.0187(9) Uani 1 1 d . . . . .
C16A C 0.3591(3) 0.1935(3) 0.65884(18) 0.0172(8) Uani 1 1 d . . . . .
C17A C 0.4031(3) 0.1413(3) 0.57473(18) 0.0171(8) Uani 1 1 d . . . . .
C18A C 0.4074(3) 0.0803(3) 0.52759(17) 0.0181(9) Uani 1 1 d . . . . .
C19A C 0.3442(3) 0.0348(3) 0.49990(18) 0.0217(9) Uani 1 1 d . . . . .
H19A H 0.286536 0.042275 0.509654 0.026 Uiso 1 1 calc R U . . .
C20A C 0.3682(3) -0.0221(3) 0.45750(19) 0.0214(8) Uani 1 1 d . . . . .
C21A C 0.4540(3) -0.0324(3) 0.44250(18) 0.0212(9) Uani 1 1 d . . . . .
C22A C 0.5174(3) 0.0088(3) 0.47251(17) 0.0203(9) Uani 1 1 d . . . . .
H22A H 0.575160 -0.001465 0.464002 0.024 Uiso 1 1 calc R U . . .
C23A C 0.4939(3) 0.0658(3) 0.51572(18) 0.0174(8) Uani 1 1 d . . . . .
C24A C 0.5428(3) 0.1151(3) 0.55726(18) 0.0181(8) Uani 1 1 d . . . . .
C25A C 0.4943(3) 0.3787(3) 0.58574(18) 0.0180(8) Uani 1 1 d . . . . .
C26A C 0.4307(3) 0.3603(3) 0.54812(18) 0.0201(9) Uani 1 1 d . . . . .
H26A H 0.413632 0.300976 0.541324 0.024 Uiso 1 1 calc R U . . .
C27A C 0.3916(3) 0.4310(3) 0.5200(2) 0.0217(9) Uani 1 1 d . . . . .
C28A C 0.4159(3) 0.5172(3) 0.5292(2) 0.0274(10) Uani 1 1 d . . . . .
H28A H 0.387912 0.564467 0.510725 0.033 Uiso 1 1 calc R U . . .
C29A C 0.4819(3) 0.5342(3) 0.5660(2) 0.0278(11) Uani 1 1 d . . . . .
H29A H 0.500520 0.593273 0.571645 0.033 Uiso 1 1 calc R U . . .
C30A C 0.5206(3) 0.4659(3) 0.5943(2) 0.0224(9) Uani 1 1 d . . . . .
H30A H 0.565278 0.478095 0.619593 0.027 Uiso 1 1 calc R U . . .
B1A B 0.5091(3) 0.2289(3) 0.6306(2) 0.0173(9) Uani 1 1 d . . . . .
I1B I 0.20313(2) 0.65290(2) 0.51537(2) 0.03071(8) Uani 1 1 d . . . . .
Cl1B Cl -0.42314(7) 0.25027(8) 0.24297(5) 0.0294(2) Uani 1 1 d . . . . .
Cl2B Cl -0.34050(8) 0.31821(11) 0.13266(5) 0.0381(3) Uani 1 1 d . . . . .
Cl3B Cl 0.29208(8) 0.39047(10) 0.11072(6) 0.0351(3) Uani 1 1 d . . . . .
Cl4B Cl 0.40502(8) 0.34884(8) 0.21549(6) 0.0315(3) Uani 1 1 d . . . . .
Cl5B Cl 0.14251(8) 0.14141(9) 0.57218(5) 0.0338(3) Uani 1 1 d . . . . .
Cl6B Cl -0.05292(8) 0.12679(8) 0.58770(5) 0.0293(2) Uani 1 1 d . . . . .
O1B O -0.0399(2) 0.5560(2) 0.36465(14) 0.0245(7) Uani 1 1 d . . . . .
N1B N -0.0897(2) 0.4277(2) 0.31838(16) 0.0194(7) Uani 1 1 d . . . . .
N2B N -0.0222(2) 0.4433(2) 0.23014(16) 0.0203(8) Uani 1 1 d . . . . .
N3B N 0.0577(2) 0.4541(2) 0.31420(15) 0.0191(7) Uani 1 1 d . . . . .
N4B N 0.1426(2) 0.3863(2) 0.38393(16) 0.0200(7) Uani 1 1 d . . . . .
N5B N -0.0059(2) 0.4010(2) 0.39718(16) 0.0194(7) Uani 1 1 d . . . . .
N6B N -0.1459(2) 0.3446(2) 0.39361(16) 0.0209(8) Uani 1 1 d . . . . .
C1B C -0.1527(3) 0.3795(3) 0.34195(19) 0.0199(9) Uani 1 1 d . . . . .
C2B C -0.2112(3) 0.3592(3) 0.2970(2) 0.0207(9) Uani 1 1 d . . . . .
C3B C -0.2889(3) 0.3172(3) 0.29675(19) 0.0197(9) Uani 1 1 d . . . . .
H3BA H -0.314563 0.297732 0.330454 0.024 Uiso 1 1 calc R U . . .
C4B C -0.3276(3) 0.3048(3) 0.2455(2) 0.0217(9) Uani 1 1 d . . . . .
C5B C -0.2894(3) 0.3323(3) 0.1950(2) 0.0221(10) Uani 1 1 d . . . . .
C6B C -0.2109(3) 0.3725(3) 0.1957(2) 0.0207(9) Uani 1 1 d . . . . .
H6BA H -0.184278 0.389477 0.161806 0.025 Uiso 1 1 calc R U . . .
C7B C -0.1719(3) 0.3874(3) 0.24648(19) 0.0199(9) Uani 1 1 d . . . . .
C8B C -0.0911(3) 0.4269(3) 0.26154(19) 0.0194(9) Uani 1 1 d . . . . .
C9B C 0.0514(3) 0.4514(3) 0.25741(18) 0.0188(8) Uani 1 1 d . . . . .
C10B C 0.1364(3) 0.4357(3) 0.23734(19) 0.0196(9) Uani 1 1 d . . . . .
C11B C 0.1689(3) 0.4278(3) 0.18293(19) 0.0222(9) Uani 1 1 d . . . . .
H11B H 0.134788 0.440198 0.151240 0.027 Uiso 1 1 calc R U . . .
C12B C 0.2512(3) 0.4018(3) 0.1768(2) 0.0222(9) Uani 1 1 d . . . . .
C13B C 0.3023(3) 0.3837(3) 0.2243(2) 0.0244(10) Uani 1 1 d . . . . .
C14B C 0.2711(3) 0.3922(3) 0.2779(2) 0.0196(9) Uani 1 1 d . . . . .
H14B H 0.305512 0.380347 0.309486 0.023 Uiso 1 1 calc R U . . .
C15B C 0.1878(3) 0.4186(3) 0.2841(2) 0.0207(9) Uani 1 1 d . . . . .
C16B C 0.1331(3) 0.4237(3) 0.3332(2) 0.0205(9) Uani 1 1 d . . . . .
C17B C 0.0721(3) 0.3696(3) 0.41388(18) 0.0230(9) Uani 1 1 d . . . . .
C18B C 0.0563(3) 0.3082(3) 0.4572(2) 0.0212(9) Uani 1 1 d . . . . .
C19B C 0.1106(3) 0.2586(3) 0.49199(19) 0.0229(9) Uani 1 1 d . . . . .
H19B H 0.170134 0.263811 0.488658 0.027 Uiso 1 1 calc R U . . .
C20B C 0.0758(3) 0.2032(3) 0.53037(19) 0.0240(9) Uani 1 1 d . . . . .
C21B C -0.0131(3) 0.1945(3) 0.53621(19) 0.0232(9) Uani 1 1 d . . . . .
C22B C -0.0660(3) 0.2389(3) 0.50085(17) 0.0203(9) Uani 1 1 d . . . . .
H22B H -0.125228 0.230312 0.503082 0.024 Uiso 1 1 calc R U . . .
C23B C -0.0323(3) 0.2962(3) 0.4619(2) 0.0212(8) Uani 1 1 d . . . . .
C24B C -0.0701(3) 0.3512(3) 0.41825(18) 0.0202(9) Uani 1 1 d . . . . .
C25B C 0.0083(3) 0.6201(3) 0.39008(19) 0.0218(9) Uani 1 1 d . . . . .
C26B C 0.0717(3) 0.6029(3) 0.4285(2) 0.0239(10) Uani 1 1 d . . . . .
H26B H 0.086894 0.543784 0.437505 0.029 Uiso 1 1 calc R U . . .
C27B C 0.1130(3) 0.6744(3) 0.45371(19) 0.0228(9) Uani 1 1 d . . . . .
C28B C 0.0934(3) 0.7601(3) 0.4401(2) 0.0263(10) Uani 1 1 d . . . . .
H28B H 0.123028 0.808109 0.456645 0.032 Uiso 1 1 calc R U . . .
C29B C 0.0289(4) 0.7756(3) 0.4015(2) 0.0320(11) Uani 1 1 d . . . . .
H29B H 0.014439 0.834616 0.391828 0.038 Uiso 1 1 calc R U . . .
C30B C -0.0139(3) 0.7061(3) 0.3772(2) 0.0276(10) Uani 1 1 d . . . . .
H30B H -0.058536 0.717416 0.351649 0.033 Uiso 1 1 calc R U . . .
B1B B -0.0182(3) 0.4670(3) 0.3514(2) 0.0197(10) 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
I1A C27A 2.088(5) . ?
Cl1A C4A 1.732(4) . ?
Cl2A C5A 1.727(5) . ?
Cl3A C12A 1.726(5) . ?
Cl4A C13A 1.740(5) . ?
Cl5A C20A 1.726(4) . ?
Cl6A C21A 1.727(4) . ?
O1A C25A 1.369(5) . ?
O1A B1A 1.425(6) . ?
N1A C1A 1.366(6) . ?
N1A C8A 1.366(5) . ?
N1A B1A 1.500(6) . ?
N2A C8A 1.340(6) . ?
N2A C9A 1.348(6) . ?
N3A C9A 1.369(5) . ?
N3A C16A 1.370(6) . ?
N3A B1A 1.509(6) . ?
N4A C17A 1.332(6) . ?
N4A C16A 1.334(6) . ?
N5A C17A 1.359(6) . ?
N5A C24A 1.376(5) . ?
N5A B1A 1.501(6) . ?
N6A C24A 1.336(6) . ?
N6A C1A 1.338(6) . ?
C1A C2A 1.453(6) . ?
C2A C3A 1.390(6) . ?
C2A C7A 1.423(7) . ?
C3A C4A 1.383(6) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.400(7) . ?
C5A C6A 1.395(7) . ?
C6A C7A 1.387(6) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.465(6) . ?
C9A C10A 1.469(6) . ?
C10A C11A 1.385(6) . ?
C10A C15A 1.411(6) . ?
C11A C12A 1.400(7) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.395(7) . ?
C13A C14A 1.381(7) . ?
C14A C15A 1.405(6) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.451(6) . ?
C17A C18A 1.459(6) . ?
C18A C19A 1.384(6) . ?
C18A C23A 1.418(6) . ?
C19A C20A 1.383(6) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.415(6) . ?
C21A C22A 1.383(7) . ?
C22A C23A 1.397(6) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.465(6) . ?
C25A C26A 1.380(7) . ?
C25A C30A 1.397(6) . ?
C26A C27A 1.406(6) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.377(7) . ?
C28A C29A 1.392(7) . ?
C28A H28A 0.9500 . ?
C29A C30A 1.378(7) . ?
C29A H29A 0.9500 . ?
C30A H30A 0.9500 . ?
I1B C27B 2.079(5) . ?
Cl1B C4B 1.725(5) . ?
Cl2B C5B 1.711(5) . ?
Cl3B C12B 1.718(5) . ?
Cl4B C13B 1.725(5) . ?
Cl5B C20B 1.729(5) . ?
Cl6B C21B 1.721(5) . ?
O1B C25B 1.375(6) . ?
O1B B1B 1.425(6) . ?
N1B C1B 1.358(6) . ?
N1B C8B 1.360(6) . ?
N1B B1B 1.504(6) . ?
N2B C9B 1.343(6) . ?
N2B C8B 1.349(6) . ?
N3B C16B 1.358(6) . ?
N3B C9B 1.363(5) . ?
N3B B1B 1.510(6) . ?
N4B C16B 1.348(6) . ?
N4B C17B 1.352(6) . ?
N5B C24B 1.363(6) . ?
N5B C17B 1.382(6) . ?
N5B B1B 1.493(6) . ?
N6B C24B 1.343(6) . ?
N6B C1B 1.348(6) . ?
C1B C2B 1.453(6) . ?
C2B C3B 1.385(6) . ?
C2B C7B 1.425(7) . ?
C3B C4B 1.383(6) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.414(7) . ?
C5B C6B 1.385(6) . ?
C6B C7B 1.381(7) . ?
C6B H6BA 0.9500 . ?
C7B C8B 1.458(6) . ?
C9B C10B 1.451(6) . ?
C10B C11B 1.405(7) . ?
C10B C15B 1.407(6) . ?
C11B C12B 1.370(7) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.422(7) . ?
C13B C14B 1.378(7) . ?
C14B C15B 1.387(6) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.462(7) . ?
C17B C18B 1.413(7) . ?
C18B C19B 1.414(6) . ?
C18B C23B 1.422(6) . ?
C19B C20B 1.360(7) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.422(7) . ?
C21B C22B 1.367(7) . ?
C22B C23B 1.380(6) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.463(6) . ?
C25B C30B 1.382(7) . ?
C25B C26B 1.387(7) . ?
C26B C27B 1.400(6) . ?
C26B H26B 0.9500 . ?
C27B C28B 1.372(7) . ?
C28B C29B 1.398(7) . ?
C28B H28B 0.9500 . ?
C29B C30B 1.378(7) . ?
C29B H29B 0.9500 . ?
C30B H30B 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
C25A O1A B1A 128.4(4) . . ?
C1A N1A C8A 114.6(4) . . ?
C1A N1A B1A 122.0(4) . . ?
C8A N1A B1A 123.0(4) . . ?
C8A N2A C9A 116.5(4) . . ?
C9A N3A C16A 112.8(4) . . ?
C9A N3A B1A 122.1(4) . . ?
C16A N3A B1A 122.9(4) . . ?
C17A N4A C16A 116.8(4) . . ?
C17A N5A C24A 113.7(4) . . ?
C17A N5A B1A 123.7(4) . . ?
C24A N5A B1A 121.7(4) . . ?
C24A N6A C1A 116.8(4) . . ?
N6A C1A N1A 122.9(4) . . ?
N6A C1A C2A 131.1(4) . . ?
N1A C1A C2A 104.8(4) . . ?
C3A C2A C7A 120.6(4) . . ?
C3A C2A C1A 131.9(4) . . ?
C7A C2A C1A 107.5(4) . . ?
C4A C3A C2A 117.9(4) . . ?
C4A C3A H3AA 121.0 . . ?
C2A C3A H3AA 121.0 . . ?
C3A C4A C5A 121.3(4) . . ?
C3A C4A Cl1A 118.8(4) . . ?
C5A C4A Cl1A 119.8(3) . . ?
C6A C5A C4A 121.3(4) . . ?
C6A C5A Cl2A 119.0(4) . . ?
C4A C5A Cl2A 119.6(3) . . ?
C7A C6A C5A 117.5(4) . . ?
C7A C6A H6AA 121.3 . . ?
C5A C6A H6AA 121.3 . . ?
C6A C7A C2A 121.0(4) . . ?
C6A C7A C8A 131.5(4) . . ?
C2A C7A C8A 107.5(4) . . ?
N2A C8A N1A 122.8(4) . . ?
N2A C8A C7A 131.7(4) . . ?
N1A C8A C7A 104.4(4) . . ?
N2A C9A N3A 123.4(4) . . ?
N2A C9A C10A 128.6(4) . . ?
N3A C9A C10A 105.5(4) . . ?
C11A C10A C15A 121.4(4) . . ?
C11A C10A C9A 131.6(4) . . ?
C15A C10A C9A 106.6(4) . . ?
C10A C11A C12A 117.3(4) . . ?
C10A C11A H11A 121.4 . . ?
C12A C11A H11A 121.4 . . ?
C13A C12A C11A 121.1(4) . . ?
C13A C12A Cl3A 120.8(4) . . ?
C11A C12A Cl3A 118.1(4) . . ?
C14A C13A C12A 122.1(4) . . ?
C14A C13A Cl4A 117.5(4) . . ?
C12A C13A Cl4A 120.3(4) . . ?
C13A C14A C15A 117.1(4) . . ?
C13A C14A H14A 121.5 . . ?
C15A C14A H14A 121.5 . . ?
C14A C15A C10A 120.9(4) . . ?
C14A C15A C16A 130.3(4) . . ?
C10A C15A C16A 108.1(4) . . ?
N4A C16A N3A 123.4(4) . . ?
N4A C16A C15A 128.9(4) . . ?
N3A C16A C15A 105.5(4) . . ?
N4A C17A N5A 123.4(4) . . ?
N4A C17A C18A 129.8(4) . . ?
N5A C17A C18A 105.6(4) . . ?
C19A C18A C23A 121.8(4) . . ?
C19A C18A C17A 130.6(4) . . ?
C23A C18A C17A 107.3(4) . . ?
C20A C19A C18A 117.4(4) . . ?
C20A C19A H19A 121.3 . . ?
C18A C19A H19A 121.3 . . ?
C19A C20A C21A 121.3(4) . . ?
C19A C20A Cl5A 118.6(4) . . ?
C21A C20A Cl5A 120.1(3) . . ?
C22A C21A C20A 121.2(4) . . ?
C22A C21A Cl6A 119.3(4) . . ?
C20A C21A Cl6A 119.5(4) . . ?
C21A C22A C23A 117.8(4) . . ?
C21A C22A H22A 121.1 . . ?
C23A C22A H22A 121.1 . . ?
C22A C23A C18A 120.2(4) . . ?
C22A C23A C24A 132.4(4) . . ?
C18A C23A C24A 107.3(4) . . ?
N6A C24A N5A 122.6(4) . . ?
N6A C24A C23A 130.6(4) . . ?
N5A C24A C23A 104.7(4) . . ?
O1A C25A C26A 124.2(4) . . ?
O1A C25A C30A 115.6(4) . . ?
C26A C25A C30A 120.2(4) . . ?
C25A C26A C27A 118.7(4) . . ?
C25A C26A H26A 120.6 . . ?
C27A C26A H26A 120.6 . . ?
C28A C27A C26A 121.3(4) . . ?
C28A C27A I1A 119.3(3) . . ?
C26A C27A I1A 119.4(3) . . ?
C27A C28A C29A 119.1(4) . . ?
C27A C28A H28A 120.5 . . ?
C29A C28A H28A 120.5 . . ?
C30A C29A C28A 120.5(4) . . ?
C30A C29A H29A 119.8 . . ?
C28A C29A H29A 119.8 . . ?
C29A C30A C25A 120.1(4) . . ?
C29A C30A H30A 119.9 . . ?
C25A C30A H30A 119.9 . . ?
O1A B1A N1A 107.8(4) . . ?
O1A B1A N5A 119.5(4) . . ?
N1A B1A N5A 102.7(3) . . ?
O1A B1A N3A 117.7(4) . . ?
N1A B1A N3A 103.6(3) . . ?
N5A B1A N3A 103.6(4) . . ?
C25B O1B B1B 129.0(4) . . ?
C1B N1B C8B 113.5(4) . . ?
C1B N1B B1B 123.2(4) . . ?
C8B N1B B1B 122.7(4) . . ?
C9B N2B C8B 116.7(4) . . ?
C16B N3B C9B 112.8(4) . . ?
C16B N3B B1B 123.2(4) . . ?
C9B N3B B1B 122.2(4) . . ?
C16B N4B C17B 117.6(4) . . ?
C24B N5B C17B 111.8(4) . . ?
C24B N5B B1B 122.8(4) . . ?
C17B N5B B1B 124.0(4) . . ?
C24B N6B C1B 116.4(4) . . ?
N6B C1B N1B 122.1(4) . . ?
N6B C1B C2B 130.3(4) . . ?
N1B C1B C2B 106.0(4) . . ?
C3B C2B C7B 121.5(4) . . ?
C3B C2B C1B 131.9(4) . . ?
C7B C2B C1B 106.5(4) . . ?
C4B C3B C2B 117.4(4) . . ?
C4B C3B H3BA 121.3 . . ?
C2B C3B H3BA 121.3 . . ?
C3B C4B C5B 121.8(4) . . ?
C3B C4B Cl1B 119.1(4) . . ?
C5B C4B Cl1B 119.1(4) . . ?
C6B C5B C4B 120.3(4) . . ?
C6B C5B Cl2B 119.4(4) . . ?
C4B C5B Cl2B 120.3(4) . . ?
C7B C6B C5B 119.0(4) . . ?
C7B C6B H6BA 120.5 . . ?
C5B C6B H6BA 120.5 . . ?
C6B C7B C2B 120.0(4) . . ?
C6B C7B C8B 132.7(4) . . ?
C2B C7B C8B 107.3(4) . . ?
N2B C8B N1B 122.8(4) . . ?
N2B C8B C7B 130.5(4) . . ?
N1B C8B C7B 105.4(4) . . ?
N2B C9B N3B 123.4(4) . . ?
N2B C9B C10B 129.2(4) . . ?
N3B C9B C10B 105.5(4) . . ?
C11B C10B C15B 120.5(4) . . ?
C11B C10B C9B 131.4(4) . . ?
C15B C10B C9B 107.8(4) . . ?
C12B C11B C10B 118.2(4) . . ?
C12B C11B H11B 120.9 . . ?
C10B C11B H11B 120.9 . . ?
C11B C12B C13B 120.8(4) . . ?
C11B C12B Cl3B 119.1(4) . . ?
C13B C12B Cl3B 120.1(4) . . ?
C14B C13B C12B 121.3(4) . . ?
C14B C13B Cl4B 118.8(4) . . ?
C12B C13B Cl4B 119.9(4) . . ?
C13B C14B C15B 117.9(4) . . ?
C13B C14B H14B 121.0 . . ?
C15B C14B H14B 121.0 . . ?
C14B C15B C10B 121.2(5) . . ?
C14B C15B C16B 131.8(4) . . ?
C10B C15B C16B 106.5(4) . . ?
N4B C16B N3B 122.8(4) . . ?
N4B C16B C15B 129.4(4) . . ?
N3B C16B C15B 105.8(4) . . ?
N4B C17B N5B 121.5(4) . . ?
N4B C17B C18B 131.1(4) . . ?
N5B C17B C18B 106.2(4) . . ?
C17B C18B C19B 132.3(4) . . ?
C17B C18B C23B 108.5(4) . . ?
C19B C18B C23B 119.2(4) . . ?
C20B C19B C18B 118.5(4) . . ?
C20B C19B H19B 120.7 . . ?
C18B C19B H19B 120.7 . . ?
C19B C20B C21B 121.7(4) . . ?
C19B C20B Cl5B 118.4(4) . . ?
C21B C20B Cl5B 120.0(4) . . ?
C22B C21B C20B 120.1(4) . . ?
C22B C21B Cl6B 120.6(4) . . ?
C20B C21B Cl6B 119.3(4) . . ?
C21B C22B C23B 119.2(4) . . ?
C21B C22B H22B 120.4 . . ?
C23B C22B H22B 120.4 . . ?
C22B C23B C18B 121.1(4) . . ?
C22B C23B C24B 132.9(4) . . ?
C18B C23B C24B 106.0(4) . . ?
N6B C24B N5B 123.2(4) . . ?
N6B C24B C23B 129.6(4) . . ?
N5B C24B C23B 105.8(4) . . ?
O1B C25B C30B 115.0(4) . . ?
O1B C25B C26B 124.4(4) . . ?
C30B C25B C26B 120.6(4) . . ?
C25B C26B C27B 118.7(4) . . ?
C25B C26B H26B 120.7 . . ?
C27B C26B H26B 120.7 . . ?
C28B C27B C26B 121.4(5) . . ?
C28B C27B I1B 118.2(3) . . ?
C26B C27B I1B 120.4(4) . . ?
C27B C28B C29B 118.7(4) . . ?
C27B C28B H28B 120.6 . . ?
C29B C28B H28B 120.6 . . ?
C30B C29B C28B 120.8(5) . . ?
C30B C29B H29B 119.6 . . ?
C28B C29B H29B 119.6 . . ?
C29B C30B C25B 119.8(5) . . ?
C29B C30B H30B 120.1 . . ?
C25B C30B H30B 120.1 . . ?
O1B B1B N5B 119.9(4) . . ?
O1B B1B N1B 107.9(4) . . ?
N5B B1B N1B 102.8(4) . . ?
O1B B1B N3B 116.4(4) . . ?
N5B B1B N3B 104.0(4) . . ?
N1B B1B N3B 103.9(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
C24A N6A C1A N1A -8.5(6) . . . . ?
C24A N6A C1A C2A 157.1(4) . . . . ?
C8A N1A C1A N6A 157.2(4) . . . . ?
B1A N1A C1A N6A -16.0(6) . . . . ?
C8A N1A C1A C2A -11.7(5) . . . . ?
B1A N1A C1A C2A 175.1(4) . . . . ?
N6A C1A C2A C3A 18.4(8) . . . . ?
N1A C1A C2A C3A -174.1(4) . . . . ?
N6A C1A C2A C7A -160.0(4) . . . . ?
N1A C1A C2A C7A 7.6(5) . . . . ?
C7A C2A C3A C4A -3.7(6) . . . . ?
C1A C2A C3A C4A 178.1(4) . . . . ?
C2A C3A C4A C5A 6.0(6) . . . . ?
C2A C3A C4A Cl1A -172.5(3) . . . . ?
C3A C4A C5A C6A -3.2(7) . . . . ?
Cl1A C4A C5A C6A 175.3(4) . . . . ?
C3A C4A C5A Cl2A 178.1(3) . . . . ?
Cl1A C4A C5A Cl2A -3.4(5) . . . . ?
C4A C5A C6A C7A -2.1(7) . . . . ?
Cl2A C5A C6A C7A 176.6(3) . . . . ?
C5A C6A C7A C2A 4.4(6) . . . . ?
C5A C6A C7A C8A -177.4(4) . . . . ?
C3A C2A C7A C6A -1.5(6) . . . . ?
C1A C2A C7A C6A 177.0(4) . . . . ?
C3A C2A C7A C8A 179.8(4) . . . . ?
C1A C2A C7A C8A -1.6(5) . . . . ?
C9A N2A C8A N1A 8.0(6) . . . . ?
C9A N2A C8A C7A -158.2(4) . . . . ?
C1A N1A C8A N2A -158.7(4) . . . . ?
B1A N1A C8A N2A 14.4(6) . . . . ?
C1A N1A C8A C7A 10.7(5) . . . . ?
B1A N1A C8A C7A -176.2(4) . . . . ?
C6A C7A C8A N2A -15.5(8) . . . . ?
C2A C7A C8A N2A 163.0(4) . . . . ?
C6A C7A C8A N1A 176.5(5) . . . . ?
C2A C7A C8A N1A -5.0(5) . . . . ?
C8A N2A C9A N3A -8.5(6) . . . . ?
C8A N2A C9A C10A 150.6(4) . . . . ?
C16A N3A C9A N2A 150.4(4) . . . . ?
B1A N3A C9A N2A -13.1(6) . . . . ?
C16A N3A C9A C10A -12.8(5) . . . . ?
B1A N3A C9A C10A -176.3(4) . . . . ?
N2A C9A C10A C11A 18.3(8) . . . . ?
N3A C9A C10A C11A -179.7(4) . . . . ?
N2A C9A C10A C15A -154.2(4) . . . . ?
N3A C9A C10A C15A 7.8(5) . . . . ?
C15A C10A C11A C12A 0.4(6) . . . . ?
C9A C10A C11A C12A -171.1(4) . . . . ?
C10A C11A C12A C13A 2.2(6) . . . . ?
C10A C11A C12A Cl3A -179.0(3) . . . . ?
C11A C12A C13A C14A -2.9(7) . . . . ?
Cl3A C12A C13A C14A 178.4(4) . . . . ?
C11A C12A C13A Cl4A 176.0(3) . . . . ?
Cl3A C12A C13A Cl4A -2.7(5) . . . . ?
C12A C13A C14A C15A 0.7(7) . . . . ?
Cl4A C13A C14A C15A -178.2(3) . . . . ?
C13A C14A C15A C10A 1.9(6) . . . . ?
C13A C14A C15A C16A 171.3(4) . . . . ?
C11A C10A C15A C14A -2.5(6) . . . . ?
C9A C10A C15A C14A 170.8(4) . . . . ?
C11A C10A C15A C16A -174.0(4) . . . . ?
C9A C10A C15A C16A -0.7(5) . . . . ?
C17A N4A C16A N3A 7.5(6) . . . . ?
C17A N4A C16A C15A -153.4(4) . . . . ?
C9A N3A C16A N4A -152.2(4) . . . . ?
B1A N3A C16A N4A 11.1(6) . . . . ?
C9A N3A C16A C15A 12.4(5) . . . . ?
B1A N3A C16A C15A 175.8(4) . . . . ?
C14A C15A C16A N4A -13.7(8) . . . . ?
C10A C15A C16A N4A 156.7(4) . . . . ?
C14A C15A C16A N3A -177.2(4) . . . . ?
C10A C15A C16A N3A -6.7(5) . . . . ?
C16A N4A C17A N5A -7.0(6) . . . . ?
C16A N4A C17A C18A 158.1(4) . . . . ?
C24A N5A C17A N4A 156.9(4) . . . . ?
B1A N5A C17A N4A -12.3(6) . . . . ?
C24A N5A C17A C18A -11.3(5) . . . . ?
B1A N5A C17A C18A 179.5(4) . . . . ?
N4A C17A C18A C19A 12.1(8) . . . . ?
N5A C17A C18A C19A 179.3(4) . . . . ?
N4A C17A C18A C23A -162.2(4) . . . . ?
N5A C17A C18A C23A 5.0(5) . . . . ?
C23A C18A C19A C20A -3.8(6) . . . . ?
C17A C18A C19A C20A -177.4(4) . . . . ?
C18A C19A C20A C21A -0.8(7) . . . . ?
C18A C19A C20A Cl5A 178.5(3) . . . . ?
C19A C20A C21A C22A 5.1(7) . . . . ?
Cl5A C20A C21A C22A -174.2(3) . . . . ?
C19A C20A C21A Cl6A -173.9(3) . . . . ?
Cl5A C20A C21A Cl6A 6.8(5) . . . . ?
C20A C21A C22A C23A -4.4(6) . . . . ?
Cl6A C21A C22A C23A 174.6(3) . . . . ?
C21A C22A C23A C18A -0.2(6) . . . . ?
C21A C22A C23A C24A 175.8(4) . . . . ?
C19A C18A C23A C22A 4.4(6) . . . . ?
C17A C18A C23A C22A 179.3(4) . . . . ?
C19A C18A C23A C24A -172.5(4) . . . . ?
C17A C18A C23A C24A 2.4(5) . . . . ?
C1A N6A C24A N5A 8.0(6) . . . . ?
C1A N6A C24A C23A -153.0(4) . . . . ?
C17A N5A C24A N6A -152.5(4) . . . . ?
B1A N5A C24A N6A 16.9(6) . . . . ?
C17A N5A C24A C23A 12.7(5) . . . . ?
B1A N5A C24A C23A -177.9(4) . . . . ?
C22A C23A C24A N6A -21.6(8) . . . . ?
C18A C23A C24A N6A 154.8(4) . . . . ?
C22A C23A C24A N5A 174.9(4) . . . . ?
C18A C23A C24A N5A -8.7(5) . . . . ?
B1A O1A C25A C26A -23.2(7) . . . . ?
B1A O1A C25A C30A 158.0(4) . . . . ?
O1A C25A C26A C27A 179.3(4) . . . . ?
C30A C25A C26A C27A -1.9(7) . . . . ?
C25A C26A C27A C28A 0.3(7) . . . . ?
C25A C26A C27A I1A 178.5(3) . . . . ?
C26A C27A C28A C29A 1.7(8) . . . . ?
I1A C27A C28A C29A -176.4(4) . . . . ?
C27A C28A C29A C30A -2.2(8) . . . . ?
C28A C29A C30A C25A 0.7(8) . . . . ?
O1A C25A C30A C29A -179.7(4) . . . . ?
C26A C25A C30A C29A 1.4(7) . . . . ?
C25A O1A B1A N1A 173.4(4) . . . . ?
C25A O1A B1A N5A 56.9(6) . . . . ?
C25A O1A B1A N3A -70.0(6) . . . . ?
C1A N1A B1A O1A -92.5(5) . . . . ?
C8A N1A B1A O1A 94.9(5) . . . . ?
C1A N1A B1A N5A 34.5(5) . . . . ?
C8A N1A B1A N5A -138.1(4) . . . . ?
C1A N1A B1A N3A 142.0(4) . . . . ?
C8A N1A B1A N3A -30.6(5) . . . . ?
C17A N5A B1A O1A -107.4(5) . . . . ?
C24A N5A B1A O1A 84.3(5) . . . . ?
C17A N5A B1A N1A 133.5(4) . . . . ?
C24A N5A B1A N1A -34.8(5) . . . . ?
C17A N5A B1A N3A 25.9(5) . . . . ?
C24A N5A B1A N3A -142.4(4) . . . . ?
C9A N3A B1A O1A -89.1(5) . . . . ?
C16A N3A B1A O1A 109.1(5) . . . . ?
C9A N3A B1A N1A 29.7(5) . . . . ?
C16A N3A B1A N1A -132.1(4) . . . . ?
C9A N3A B1A N5A 136.6(4) . . . . ?
C16A N3A B1A N5A -25.2(5) . . . . ?
C24B N6B C1B N1B -7.3(6) . . . . ?
C24B N6B C1B C2B 156.1(5) . . . . ?
C8B N1B C1B N6B 154.7(4) . . . . ?
B1B N1B C1B N6B -16.9(7) . . . . ?
C8B N1B C1B C2B -12.1(5) . . . . ?
B1B N1B C1B C2B 176.2(4) . . . . ?
N6B C1B C2B C3B 19.3(8) . . . . ?
N1B C1B C2B C3B -175.3(5) . . . . ?
N6B C1B C2B C7B -157.5(5) . . . . ?
N1B C1B C2B C7B 8.0(5) . . . . ?
C7B C2B C3B C4B -0.9(7) . . . . ?
C1B C2B C3B C4B -177.3(5) . . . . ?
C2B C3B C4B C5B 1.0(7) . . . . ?
C2B C3B C4B Cl1B 178.4(3) . . . . ?
C3B C4B C5B C6B 0.3(7) . . . . ?
Cl1B C4B C5B C6B -177.0(4) . . . . ?
C3B C4B C5B Cl2B -178.3(4) . . . . ?
Cl1B C4B C5B Cl2B 4.3(6) . . . . ?
C4B C5B C6B C7B -1.8(7) . . . . ?
Cl2B C5B C6B C7B 176.9(4) . . . . ?
C5B C6B C7B C2B 1.9(7) . . . . ?
C5B C6B C7B C8B 179.6(5) . . . . ?
C3B C2B C7B C6B -0.6(7) . . . . ?
C1B C2B C7B C6B 176.6(4) . . . . ?
C3B C2B C7B C8B -178.8(4) . . . . ?
C1B C2B C7B C8B -1.6(5) . . . . ?
C9B N2B C8B N1B 7.0(6) . . . . ?
C9B N2B C8B C7B -157.7(4) . . . . ?
C1B N1B C8B N2B -157.0(4) . . . . ?
B1B N1B C8B N2B 14.7(7) . . . . ?
C1B N1B C8B C7B 11.0(5) . . . . ?
B1B N1B C8B C7B -177.3(4) . . . . ?
C6B C7B C8B N2B -16.4(8) . . . . ?
C2B C7B C8B N2B 161.5(4) . . . . ?
C6B C7B C8B N1B 176.8(5) . . . . ?
C2B C7B C8B N1B -5.3(5) . . . . ?
C8B N2B C9B N3B -7.9(6) . . . . ?
C8B N2B C9B C10B 154.1(4) . . . . ?
C16B N3B C9B N2B 152.6(4) . . . . ?
B1B N3B C9B N2B -12.7(6) . . . . ?
C16B N3B C9B C10B -13.0(5) . . . . ?
B1B N3B C9B C10B -178.4(4) . . . . ?
N2B C9B C10B C11B 16.5(8) . . . . ?
N3B C9B C10B C11B -179.0(5) . . . . ?
N2B C9B C10B C15B -157.1(4) . . . . ?
N3B C9B C10B C15B 7.4(5) . . . . ?
C15B C10B C11B C12B 1.0(6) . . . . ?
C9B C10B C11B C12B -172.0(4) . . . . ?
C10B C11B C12B C13B -0.4(7) . . . . ?
C10B C11B C12B Cl3B 179.3(3) . . . . ?
C11B C12B C13B C14B -0.3(7) . . . . ?
Cl3B C12B C13B C14B -179.9(4) . . . . ?
C11B C12B C13B Cl4B 178.6(3) . . . . ?
Cl3B C12B C13B Cl4B -1.0(5) . . . . ?
C12B C13B C14B C15B 0.3(7) . . . . ?
Cl4B C13B C14B C15B -178.7(3) . . . . ?
C13B C14B C15B C10B 0.4(7) . . . . ?
C13B C14B C15B C16B 171.7(5) . . . . ?
C11B C10B C15B C14B -1.1(7) . . . . ?
C9B C10B C15B C14B 173.4(4) . . . . ?
C11B C10B C15B C16B -174.3(4) . . . . ?
C9B C10B C15B C16B 0.2(5) . . . . ?
C17B N4B C16B N3B 7.8(6) . . . . ?
C17B N4B C16B C15B -153.4(5) . . . . ?
C9B N3B C16B N4B -151.9(4) . . . . ?
B1B N3B C16B N4B 13.3(7) . . . . ?
C9B N3B C16B C15B 13.2(5) . . . . ?
B1B N3B C16B C15B 178.3(4) . . . . ?
C14B C15B C16B N4B -16.2(8) . . . . ?
C10B C15B C16B N4B 156.0(5) . . . . ?
C14B C15B C16B N3B -179.9(5) . . . . ?
C10B C15B C16B N3B -7.7(5) . . . . ?
C16B N4B C17B N5B -9.3(6) . . . . ?
C16B N4B C17B C18B 156.3(5) . . . . ?
C24B N5B C17B N4B 156.0(4) . . . . ?
B1B N5B C17B N4B -10.4(7) . . . . ?
C24B N5B C17B C18B -12.8(5) . . . . ?
B1B N5B C17B C18B -179.1(4) . . . . ?
N4B C17B C18B C19B 16.4(8) . . . . ?
N5B C17B C18B C19B -176.4(5) . . . . ?
N4B C17B C18B C23B -160.9(5) . . . . ?
N5B C17B C18B C23B 6.3(5) . . . . ?
C17B C18B C19B C20B -179.5(5) . . . . ?
C23B C18B C19B C20B -2.4(6) . . . . ?
C18B C19B C20B C21B -0.2(7) . . . . ?
C18B C19B C20B Cl5B 179.1(3) . . . . ?
C19B C20B C21B C22B 3.5(7) . . . . ?
Cl5B C20B C21B C22B -175.8(3) . . . . ?
C19B C20B C21B Cl6B -177.2(4) . . . . ?
Cl5B C20B C21B Cl6B 3.5(5) . . . . ?
C20B C21B C22B C23B -4.0(7) . . . . ?
Cl6B C21B C22B C23B 176.7(3) . . . . ?
C21B C22B C23B C18B 1.4(7) . . . . ?
C21B C22B C23B C24B 178.6(5) . . . . ?
C17B C18B C23B C22B 179.6(4) . . . . ?
C19B C18B C23B C22B 1.8(7) . . . . ?
C17B C18B C23B C24B 1.7(5) . . . . ?
C19B C18B C23B C24B -176.1(4) . . . . ?
C1B N6B C24B N5B 9.5(6) . . . . ?
C1B N6B C24B C23B -155.1(5) . . . . ?
C17B N5B C24B N6B -154.0(4) . . . . ?
B1B N5B C24B N6B 12.5(6) . . . . ?
C17B N5B C24B C23B 13.7(5) . . . . ?
B1B N5B C24B C23B -179.7(4) . . . . ?
C22B C23B C24B N6B -20.0(8) . . . . ?
C18B C23B C24B N6B 157.6(4) . . . . ?
C22B C23B C24B N5B 173.4(5) . . . . ?
C18B C23B C24B N5B -9.1(5) . . . . ?
B1B O1B C25B C30B 154.3(5) . . . . ?
B1B O1B C25B C26B -29.2(7) . . . . ?
O1B C25B C26B C27B -176.5(4) . . . . ?
C30B C25B C26B C27B -0.2(7) . . . . ?
C25B C26B C27B C28B -1.7(7) . . . . ?
C25B C26B C27B I1B 176.0(3) . . . . ?
C26B C27B C28B C29B 2.0(7) . . . . ?
I1B C27B C28B C29B -175.7(4) . . . . ?
C27B C28B C29B C30B -0.3(8) . . . . ?
C28B C29B C30B C25B -1.5(8) . . . . ?
O1B C25B C30B C29B 178.4(5) . . . . ?
C26B C25B C30B C29B 1.8(8) . . . . ?
C25B O1B B1B N5B 68.9(6) . . . . ?
C25B O1B B1B N1B -174.0(4) . . . . ?
C25B O1B B1B N3B -57.7(6) . . . . ?
C24B N5B B1B O1B 89.2(5) . . . . ?
C17B N5B B1B O1B -105.9(5) . . . . ?
C24B N5B B1B N1B -30.5(5) . . . . ?
C17B N5B B1B N1B 134.4(4) . . . . ?
C24B N5B B1B N3B -138.6(4) . . . . ?
C17B N5B B1B N3B 26.4(5) . . . . ?
C1B N1B B1B O1B -94.9(5) . . . . ?
C8B N1B B1B O1B 94.3(5) . . . . ?
C1B N1B B1B N5B 32.8(5) . . . . ?
C8B N1B B1B N5B -138.0(4) . . . . ?
C1B N1B B1B N3B 140.9(4) . . . . ?
C8B N1B B1B N3B -29.9(6) . . . . ?
C16B N3B B1B O1B 106.6(5) . . . . ?
C9B N3B B1B O1B -89.6(5) . . . . ?
C16B N3B B1B N5B -27.7(5) . . . . ?
C9B N3B B1B N5B 136.1(4) . . . . ?
C16B N3B B1B N1B -134.9(4) . . . . ?
C9B N3B B1B N1B 28.9(5) . . . . ?

_refine_diff_density_max         1.252
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.076



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chlorobenzene/heptane'
####################################################################### 
# 
# 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_d19200_a
_database_code_depnum_ccdc_archive 'CCDC 2087099'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        NaphO-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H13 B Cl6 N6 O'
_chemical_formula_sum            'C34 H13 B Cl6 N6 O'
_chemical_formula_weight         745.01

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'
O O 0.0106 0.0060 '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           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                   10.4162(2)
_cell_length_b                   22.7272(5)
_cell_length_c                   13.1011(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.322(1)
_cell_angle_gamma                90
_cell_volume                     3068.78(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Shard
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.603
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6845
_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            38079
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.792
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7069
_reflns_number_gt                5368
_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 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)+(0.0322P)²+3.5287P] 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         7069
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Cl1 Cl 1.38876(5) 0.45608(3) 0.61083(5) 0.03459(14) Uani 1 1 d . . . . .
Cl2 Cl 1.40274(5) 0.33167(3) 0.71737(5) 0.03805(15) Uani 1 1 d . . . . .
Cl3 Cl 0.93334(6) 0.01168(3) 0.34498(5) 0.03917(15) Uani 1 1 d . . . . .
Cl4 Cl 0.75066(6) 0.03370(3) 0.13556(4) 0.03476(14) Uani 1 1 d . . . . .
Cl5 Cl 0.57535(5) 0.46339(3) -0.12859(4) 0.03291(14) Uani 1 1 d . . . . .
Cl6 Cl 0.72500(6) 0.56642(3) 0.00024(5) 0.03859(15) Uani 1 1 d . . . . .
O1 O 0.61408(14) 0.34069(7) 0.47036(11) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.84690(16) 0.34495(8) 0.47282(13) 0.0223(4) Uani 1 1 d . . . . .
N2 N 0.90724(17) 0.24580(8) 0.51397(13) 0.0255(4) Uani 1 1 d . . . . .
N3 N 0.73363(16) 0.26706(8) 0.37890(13) 0.0220(4) Uani 1 1 d . . . . .
N4 N 0.64994(16) 0.28362(8) 0.20155(13) 0.0232(4) Uani 1 1 d . . . . .
N5 N 0.71475(16) 0.36340(8) 0.31405(13) 0.0226(4) Uani 1 1 d . . . . .
N6 N 0.86889(17) 0.43473(8) 0.38363(14) 0.0241(4) Uani 1 1 d . . . . .
C1 C 0.9094(2) 0.39620(9) 0.45874(16) 0.0223(4) Uani 1 1 d . . . . .
C2 C 1.0351(2) 0.39201(10) 0.52412(16) 0.0233(4) Uani 1 1 d . . . . .
C3 C 1.1410(2) 0.42994(10) 0.53744(16) 0.0248(4) Uani 1 1 d . . . . .
H3A H 1.135921 0.467188 0.507727 0.030 Uiso 1 1 calc R U . . .
C4 C 1.2541(2) 0.41051(10) 0.59631(16) 0.0259(5) Uani 1 1 d . . . . .
C5 C 1.2623(2) 0.35432(11) 0.64135(16) 0.0265(5) Uani 1 1 d . . . . .
C6 C 1.1591(2) 0.31546(10) 0.62527(16) 0.0259(5) Uani 1 1 d . . . . .
H6A H 1.166121 0.277627 0.652570 0.031 Uiso 1 1 calc R U . . .
C7 C 1.0444(2) 0.33475(10) 0.56694(15) 0.0238(4) Uani 1 1 d . . . . .
C8 C 0.9262(2) 0.30365(10) 0.52569(15) 0.0238(4) Uani 1 1 d . . . . .
C9 C 0.8172(2) 0.22863(10) 0.43543(16) 0.0237(4) Uani 1 1 d . . . . .
C10 C 0.8133(2) 0.17506(10) 0.37586(16) 0.0237(4) Uani 1 1 d . . . . .
C11 C 0.8787(2) 0.12189(10) 0.39536(17) 0.0267(5) Uani 1 1 d . . . . .
H11A H 0.932774 0.115320 0.457254 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8605(2) 0.07942(10) 0.31981(18) 0.0272(5) Uani 1 1 d . . . . .
C13 C 0.7805(2) 0.08976(10) 0.22513(17) 0.0254(5) Uani 1 1 d . . . . .
C14 C 0.7194(2) 0.14316(10) 0.20317(16) 0.0235(4) Uani 1 1 d . . . . .
H14A H 0.669417 0.150085 0.139555 0.028 Uiso 1 1 calc R U . . .
C15 C 0.73520(19) 0.18624(10) 0.27941(16) 0.0223(4) Uani 1 1 d . . . . .
C16 C 0.69274(19) 0.24720(10) 0.28057(16) 0.0224(4) Uani 1 1 d . . . . .
C17 C 0.66663(19) 0.34148(10) 0.21881(16) 0.0232(4) Uani 1 1 d . . . . .
C18 C 0.6698(2) 0.39097(10) 0.14766(16) 0.0238(4) Uani 1 1 d . . . . .
C19 C 0.6233(2) 0.39859(10) 0.04357(16) 0.0249(5) Uani 1 1 d . . . . .
H19A H 0.581300 0.368097 0.004862 0.030 Uiso 1 1 calc R U . . .
C20 C 0.6411(2) 0.45253(10) -0.00108(16) 0.0266(5) Uani 1 1 d . . . . .
C21 C 0.7076(2) 0.49848(10) 0.05588(18) 0.0280(5) Uani 1 1 d . . . . .
C22 C 0.7564(2) 0.49131(10) 0.15920(17) 0.0263(5) Uani 1 1 d . . . . .
H22A H 0.801341 0.521511 0.196724 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7363(2) 0.43765(10) 0.20502(16) 0.0248(5) Uani 1 1 d . . . . .
C24 C 0.7743(2) 0.41643(10) 0.30982(16) 0.0232(4) Uani 1 1 d . . . . .
C25 C 0.4891(2) 0.32254(11) 0.43335(16) 0.0259(5) Uani 1 1 d . . . . .
C26 C 0.4458(2) 0.26907(11) 0.47205(18) 0.0325(5) Uani 1 1 d . . . . .
H26A H 0.501864 0.246657 0.518255 0.039 Uiso 1 1 calc R U . . .
C27 C 0.3214(2) 0.25042(11) 0.44140(19) 0.0363(6) Uani 1 1 d . . . . .
H27A H 0.293268 0.215265 0.466970 0.044 Uiso 1 1 calc R U . . .
C28 C 0.2354(2) 0.28395(11) 0.37145(18) 0.0305(5) Uani 1 1 d . . . . .
C29 C 0.1049(2) 0.26550(13) 0.3368(2) 0.0401(6) Uani 1 1 d . . . . .
H29A H 0.074636 0.230431 0.361160 0.048 Uiso 1 1 calc R U . . .
C30 C 0.0251(2) 0.29865(14) 0.2691(2) 0.0440(7) Uani 1 1 d . . . . .
H30A H -0.059111 0.285892 0.246591 0.053 Uiso 1 1 calc R U . . .
C31 C 0.0682(3) 0.35212(14) 0.2325(2) 0.0451(7) Uani 1 1 d . . . . .
H31A H 0.012203 0.374665 0.186448 0.054 Uiso 1 1 calc R U . . .
C32 C 0.1920(3) 0.37126(13) 0.2639(2) 0.0413(6) Uani 1 1 d . . . . .
H32A H 0.219600 0.406788 0.239383 0.050 Uiso 1 1 calc R U . . .
C33 C 0.2779(2) 0.33752(10) 0.33325(17) 0.0284(5) Uani 1 1 d . . . . .
C34 C 0.4088(2) 0.35624(11) 0.36678(17) 0.0299(5) Uani 1 1 d . . . . .
H34A H 0.438519 0.391506 0.342815 0.036 Uiso 1 1 calc R U . . .
B1 B 0.7180(2) 0.32937(11) 0.41220(18) 0.0234(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.732(2) . ?
Cl2 C5 1.725(2) . ?
Cl3 C12 1.727(2) . ?
Cl4 C13 1.730(2) . ?
Cl5 C20 1.729(2) . ?
Cl6 C21 1.728(2) . ?
O1 C25 1.385(2) . ?
O1 B1 1.434(3) . ?
N1 C1 1.360(3) . ?
N1 C8 1.370(3) . ?
N1 B1 1.500(3) . ?
N2 C8 1.335(3) . ?
N2 C9 1.346(3) . ?
N3 C9 1.372(3) . ?
N3 C16 1.373(3) . ?
N3 B1 1.498(3) . ?
N4 C17 1.341(3) . ?
N4 C16 1.350(3) . ?
N5 C24 1.360(3) . ?
N5 C17 1.369(3) . ?
N5 B1 1.497(3) . ?
N6 C1 1.339(3) . ?
N6 C24 1.343(3) . ?
C1 C2 1.461(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.415(3) . ?
C3 C4 1.384(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.404(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.393(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.454(3) . ?
C9 C10 1.444(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.423(3) . ?
C11 C12 1.376(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.410(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.391(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.455(3) . ?
C17 C18 1.464(3) . ?
C18 C19 1.390(3) . ?
C18 C23 1.421(3) . ?
C19 C20 1.382(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.406(3) . ?
C21 C22 1.385(3) . ?
C22 C23 1.388(3) . ?
C22 H22A 0.9300 . ?
C23 C24 1.455(3) . ?
C25 C34 1.355(3) . ?
C25 C26 1.415(3) . ?
C26 C27 1.367(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.409(4) . ?
C27 H27A 0.9300 . ?
C28 C33 1.412(3) . ?
C28 C29 1.433(3) . ?
C29 C30 1.354(4) . ?
C29 H29A 0.9300 . ?
C30 C31 1.404(4) . ?
C30 H30A 0.9300 . ?
C31 C32 1.367(4) . ?
C31 H31A 0.9300 . ?
C32 C33 1.406(3) . ?
C32 H32A 0.9300 . ?
C33 C34 1.435(3) . ?
C34 H34A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O1 B1 120.27(16) . . ?
C1 N1 C8 112.95(17) . . ?
C1 N1 B1 122.66(18) . . ?
C8 N1 B1 122.27(19) . . ?
C8 N2 C9 116.67(19) . . ?
C9 N3 C16 112.56(18) . . ?
C9 N3 B1 122.14(17) . . ?
C16 N3 B1 123.50(18) . . ?
C17 N4 C16 116.83(18) . . ?
C24 N5 C17 113.22(18) . . ?
C24 N5 B1 122.63(17) . . ?
C17 N5 B1 123.67(18) . . ?
C1 N6 C24 116.54(19) . . ?
N6 C1 N1 123.64(18) . . ?
N6 C1 C2 129.3(2) . . ?
N1 C1 C2 105.70(18) . . ?
C3 C2 C7 120.87(19) . . ?
C3 C2 C1 131.3(2) . . ?
C7 C2 C1 107.25(18) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 H3A 121.1 . . ?
C2 C3 H3A 121.1 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 Cl1 118.75(18) . . ?
C5 C4 Cl1 119.93(16) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 Cl2 118.21(18) . . ?
C4 C5 Cl2 120.58(17) . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 H6A 121.0 . . ?
C7 C6 H6A 121.0 . . ?
C6 C7 C2 120.7(2) . . ?
C6 C7 C8 131.6(2) . . ?
C2 C7 C8 107.12(18) . . ?
N2 C8 N1 123.23(18) . . ?
N2 C8 C7 128.7(2) . . ?
N1 C8 C7 105.71(19) . . ?
N2 C9 N3 123.1(2) . . ?
N2 C9 C10 128.3(2) . . ?
N3 C9 C10 106.20(17) . . ?
C11 C10 C15 121.3(2) . . ?
C11 C10 C9 131.1(2) . . ?
C15 C10 C9 107.29(19) . . ?
C12 C11 C10 117.6(2) . . ?
C12 C11 H11A 121.2 . . ?
C10 C11 H11A 121.2 . . ?
C11 C12 C13 121.2(2) . . ?
C11 C12 Cl3 118.49(17) . . ?
C13 C12 Cl3 120.25(18) . . ?
C14 C13 C12 121.7(2) . . ?
C14 C13 Cl4 118.27(17) . . ?
C12 C13 Cl4 119.97(18) . . ?
C13 C14 C15 117.76(19) . . ?
C13 C14 H14A 121.1 . . ?
C15 C14 H14A 121.1 . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 C16 132.31(19) . . ?
C10 C15 C16 107.24(18) . . ?
N4 C16 N3 122.77(19) . . ?
N4 C16 C15 130.01(19) . . ?
N3 C16 C15 105.62(18) . . ?
N4 C17 N5 122.13(19) . . ?
N4 C17 C18 131.30(19) . . ?
N5 C17 C18 105.16(18) . . ?
C19 C18 C23 120.0(2) . . ?
C19 C18 C17 133.1(2) . . ?
C23 C18 C17 106.92(18) . . ?
C20 C19 C18 118.5(2) . . ?
C20 C19 H19A 120.8 . . ?
C18 C19 H19A 120.8 . . ?
C19 C20 C21 121.3(2) . . ?
C19 C20 Cl5 118.48(17) . . ?
C21 C20 Cl5 120.16(18) . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 Cl6 118.10(18) . . ?
C20 C21 Cl6 120.90(18) . . ?
C21 C22 C23 117.9(2) . . ?
C21 C22 H22A 121.0 . . ?
C23 C22 H22A 121.0 . . ?
C22 C23 C18 121.3(2) . . ?
C22 C23 C24 131.4(2) . . ?
C18 C23 C24 107.25(19) . . ?
N6 C24 N5 122.46(19) . . ?
N6 C24 C23 130.4(2) . . ?
N5 C24 C23 105.59(18) . . ?
C34 C25 O1 121.2(2) . . ?
C34 C25 C26 121.1(2) . . ?
O1 C25 C26 117.6(2) . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26A 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C26 C27 C28 120.6(2) . . ?
C26 C27 H27A 119.7 . . ?
C28 C27 H27A 119.7 . . ?
C27 C28 C33 119.6(2) . . ?
C27 C28 C29 122.2(2) . . ?
C33 C28 C29 118.2(2) . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 H29A 119.7 . . ?
C28 C29 H29A 119.7 . . ?
C29 C30 C31 120.6(2) . . ?
C29 C30 H30A 119.7 . . ?
C31 C30 H30A 119.7 . . ?
C32 C31 C30 120.5(3) . . ?
C32 C31 H31A 119.8 . . ?
C30 C31 H31A 119.8 . . ?
C31 C32 C33 120.4(3) . . ?
C31 C32 H32A 119.8 . . ?
C33 C32 H32A 119.8 . . ?
C32 C33 C28 119.8(2) . . ?
C32 C33 C34 121.6(2) . . ?
C28 C33 C34 118.7(2) . . ?
C25 C34 C33 120.0(2) . . ?
C25 C34 H34A 120.0 . . ?
C33 C34 H34A 120.0 . . ?
O1 B1 N5 116.04(19) . . ?
O1 B1 N3 116.55(19) . . ?
N5 B1 N3 103.19(17) . . ?
O1 B1 N1 111.28(17) . . ?
N5 B1 N1 103.87(18) . . ?
N3 B1 N1 104.50(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
C24 N6 C1 N1 -11.1(3) . . . . ?
C24 N6 C1 C2 153.8(2) . . . . ?
C8 N1 C1 N6 157.08(19) . . . . ?
B1 N1 C1 N6 -6.7(3) . . . . ?
C8 N1 C1 C2 -10.9(2) . . . . ?
B1 N1 C1 C2 -174.65(18) . . . . ?
N6 C1 C2 C3 9.7(4) . . . . ?
N1 C1 C2 C3 176.7(2) . . . . ?
N6 C1 C2 C7 -161.7(2) . . . . ?
N1 C1 C2 C7 5.4(2) . . . . ?
C7 C2 C3 C4 -1.9(3) . . . . ?
C1 C2 C3 C4 -172.2(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 Cl1 178.10(16) . . . . ?
C3 C4 C5 C6 2.5(3) . . . . ?
Cl1 C4 C5 C6 -175.58(17) . . . . ?
C3 C4 C5 Cl2 -178.22(17) . . . . ?
Cl1 C4 C5 Cl2 3.7(3) . . . . ?
C4 C5 C6 C7 -3.0(3) . . . . ?
Cl2 C5 C6 C7 177.70(16) . . . . ?
C5 C6 C7 C2 1.1(3) . . . . ?
C5 C6 C7 C8 171.3(2) . . . . ?
C3 C2 C7 C6 1.3(3) . . . . ?
C1 C2 C7 C6 173.78(19) . . . . ?
C3 C2 C7 C8 -170.99(19) . . . . ?
C1 C2 C7 C8 1.5(2) . . . . ?
C9 N2 C8 N1 10.0(3) . . . . ?
C9 N2 C8 C7 -149.9(2) . . . . ?
C1 N1 C8 N2 -152.0(2) . . . . ?
B1 N1 C8 N2 11.8(3) . . . . ?
C1 N1 C8 C7 11.8(2) . . . . ?
B1 N1 C8 C7 175.66(18) . . . . ?
C6 C7 C8 N2 -16.2(4) . . . . ?
C2 C7 C8 N2 154.9(2) . . . . ?
C6 C7 C8 N1 -178.9(2) . . . . ?
C2 C7 C8 N1 -7.7(2) . . . . ?
C8 N2 C9 N3 -9.9(3) . . . . ?
C8 N2 C9 C10 149.9(2) . . . . ?
C16 N3 C9 N2 153.1(2) . . . . ?
B1 N3 C9 N2 -12.1(3) . . . . ?
C16 N3 C9 C10 -10.5(2) . . . . ?
B1 N3 C9 C10 -175.69(18) . . . . ?
N2 C9 C10 C11 17.1(4) . . . . ?
N3 C9 C10 C11 179.6(2) . . . . ?
N2 C9 C10 C15 -156.7(2) . . . . ?
N3 C9 C10 C15 5.7(2) . . . . ?
C15 C10 C11 C12 -2.9(3) . . . . ?
C9 C10 C11 C12 -176.1(2) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C10 C11 C12 Cl3 -176.47(16) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
Cl3 C12 C13 C14 179.11(17) . . . . ?
C11 C12 C13 Cl4 -175.46(17) . . . . ?
Cl3 C12 C13 Cl4 2.2(3) . . . . ?
C12 C13 C14 C15 -2.4(3) . . . . ?
Cl4 C13 C14 C15 174.54(16) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C13 C14 C15 C16 175.6(2) . . . . ?
C11 C10 C15 C14 2.0(3) . . . . ?
C9 C10 C15 C14 176.56(19) . . . . ?
C11 C10 C15 C16 -174.07(19) . . . . ?
C9 C10 C15 C16 0.5(2) . . . . ?
C17 N4 C16 N3 9.7(3) . . . . ?
C17 N4 C16 C15 -153.7(2) . . . . ?
C9 N3 C16 N4 -156.10(19) . . . . ?
B1 N3 C16 N4 8.9(3) . . . . ?
C9 N3 C16 C15 10.8(2) . . . . ?
B1 N3 C16 C15 175.72(18) . . . . ?
C14 C15 C16 N4 -16.4(4) . . . . ?
C10 C15 C16 N4 159.0(2) . . . . ?
C14 C15 C16 N3 178.1(2) . . . . ?
C10 C15 C16 N3 -6.6(2) . . . . ?
C16 N4 C17 N5 -5.3(3) . . . . ?
C16 N4 C17 C18 159.1(2) . . . . ?
C24 N5 C17 N4 154.21(19) . . . . ?
B1 N5 C17 N4 -18.0(3) . . . . ?
C24 N5 C17 C18 -13.7(2) . . . . ?
B1 N5 C17 C18 174.14(18) . . . . ?
N4 C17 C18 C19 20.8(4) . . . . ?
N5 C17 C18 C19 -172.9(2) . . . . ?
N4 C17 C18 C23 -158.8(2) . . . . ?
N5 C17 C18 C23 7.4(2) . . . . ?
C23 C18 C19 C20 -1.4(3) . . . . ?
C17 C18 C19 C20 179.0(2) . . . . ?
C18 C19 C20 C21 1.7(3) . . . . ?
C18 C19 C20 Cl5 -176.37(16) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
Cl5 C20 C21 C22 177.44(17) . . . . ?
C19 C20 C21 Cl6 -178.07(16) . . . . ?
Cl5 C20 C21 Cl6 0.0(3) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
Cl6 C21 C22 C23 176.70(16) . . . . ?
C21 C22 C23 C18 1.1(3) . . . . ?
C21 C22 C23 C24 -180.0(2) . . . . ?
C19 C18 C23 C22 0.0(3) . . . . ?
C17 C18 C23 C22 179.68(19) . . . . ?
C19 C18 C23 C24 -179.15(19) . . . . ?
C17 C18 C23 C24 0.5(2) . . . . ?
C1 N6 C24 N5 4.9(3) . . . . ?
C1 N6 C24 C23 -158.6(2) . . . . ?
C17 N5 C24 N6 -153.01(19) . . . . ?
B1 N5 C24 N6 19.3(3) . . . . ?
C17 N5 C24 C23 14.0(2) . . . . ?
B1 N5 C24 C23 -173.66(18) . . . . ?
C22 C23 C24 N6 -21.8(4) . . . . ?
C18 C23 C24 N6 157.2(2) . . . . ?
C22 C23 C24 N5 172.6(2) . . . . ?
C18 C23 C24 N5 -8.4(2) . . . . ?
B1 O1 C25 C34 -85.4(3) . . . . ?
B1 O1 C25 C26 98.0(2) . . . . ?
C34 C25 C26 C27 0.7(4) . . . . ?
O1 C25 C26 C27 177.2(2) . . . . ?
C25 C26 C27 C28 0.0(4) . . . . ?
C26 C27 C28 C33 -0.5(4) . . . . ?
C26 C27 C28 C29 179.4(2) . . . . ?
C27 C28 C29 C30 -179.6(2) . . . . ?
C33 C28 C29 C30 0.2(3) . . . . ?
C28 C29 C30 C31 -0.8(4) . . . . ?
C29 C30 C31 C32 0.6(4) . . . . ?
C30 C31 C32 C33 0.2(4) . . . . ?
C31 C32 C33 C28 -0.8(4) . . . . ?
C31 C32 C33 C34 179.3(2) . . . . ?
C27 C28 C33 C32 -179.6(2) . . . . ?
C29 C28 C33 C32 0.6(3) . . . . ?
C27 C28 C33 C34 0.3(3) . . . . ?
C29 C28 C33 C34 -179.6(2) . . . . ?
O1 C25 C34 C33 -177.25(19) . . . . ?
C26 C25 C34 C33 -0.8(3) . . . . ?
C32 C33 C34 C25 -179.8(2) . . . . ?
C28 C33 C34 C25 0.4(3) . . . . ?
C25 O1 B1 N5 69.6(3) . . . . ?
C25 O1 B1 N3 -52.3(3) . . . . ?
C25 O1 B1 N1 -171.98(19) . . . . ?
C24 N5 B1 O1 90.7(2) . . . . ?
C17 N5 B1 O1 -97.8(2) . . . . ?
C24 N5 B1 N3 -140.56(19) . . . . ?
C17 N5 B1 N3 30.9(3) . . . . ?
C24 N5 B1 N1 -31.7(3) . . . . ?
C17 N5 B1 N1 139.77(19) . . . . ?
C9 N3 B1 O1 -94.4(2) . . . . ?
C16 N3 B1 O1 102.0(2) . . . . ?
C9 N3 B1 N5 137.18(18) . . . . ?
C16 N3 B1 N5 -26.4(3) . . . . ?
C9 N3 B1 N1 28.8(3) . . . . ?
C16 N3 B1 N1 -134.74(19) . . . . ?
C1 N1 B1 O1 -99.9(2) . . . . ?
C8 N1 B1 O1 97.8(2) . . . . ?
C1 N1 B1 N5 25.6(3) . . . . ?
C8 N1 B1 N5 -136.65(19) . . . . ?
C1 N1 B1 N3 133.47(19) . . . . ?
C8 N1 B1 N3 -28.8(3) . . . . ?

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.063



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene/heptane'
####################################################################### 
# 
# 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_d19227a_a
_database_code_depnum_ccdc_archive 'CCDC 2087103'
loop_
_audit_author_name
_audit_author_address
'Alan Lough'
;University of Toronto
Canada
;
_audit_update_record             
;
2021-05-31 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        IPhO-Cl6BsubPc
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H10 B Cl6 I N6 O'
_chemical_formula_sum            'C30 H10 B Cl6 I N6 O'
_chemical_formula_weight         820.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.8587(3)
_cell_length_b                   15.1167(3)
_cell_length_c                   23.9409(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5739.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.25

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_F_000             3200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.715
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6956
_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 PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63792
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.701
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13120
_reflns_number_gt                11694
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.997

_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 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)+(0.0437P)²+1.5314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     diff
_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_abs_structure_details 
; 
 Flack x determined using 5186 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.008(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         13120
_refine_ls_number_parameters     811
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
I1A I 0.29722(2) 0.40475(2) 0.46171(2) 0.02293(8) Uani 1 1 d . . . . .
Cl1A Cl 0.92565(8) 0.00202(8) 0.70227(6) 0.0219(3) Uani 1 1 d . . . . .
Cl2A Cl 0.85928(9) 0.05232(10) 0.82080(6) 0.0281(3) Uani 1 1 d . . . . .
Cl3A Cl 0.23309(10) 0.15801(10) 0.88998(6) 0.0324(3) Uani 1 1 d . . . . .
Cl4A Cl 0.10654(9) 0.11348(10) 0.79197(7) 0.0315(3) Uani 1 1 d . . . . .
Cl5A Cl 0.29091(9) -0.08178(11) 0.42313(7) 0.0330(3) Uani 1 1 d . . . . .
Cl6A Cl 0.47967(10) -0.09613(9) 0.38499(6) 0.0275(3) Uani 1 1 d . . . . .
O1A O 0.5368(2) 0.3156(2) 0.61583(16) 0.0173(7) Uani 1 1 d . . . . .
N1A N 0.5819(3) 0.1822(3) 0.65813(18) 0.0149(8) Uani 1 1 d . . . . .
N2A N 0.5314(3) 0.2009(3) 0.75073(18) 0.0157(8) Uani 1 1 d . . . . .
N3A N 0.4390(3) 0.2203(3) 0.67271(18) 0.0151(8) Uani 1 1 d . . . . .
N4A N 0.3397(3) 0.1593(3) 0.60927(18) 0.0163(9) Uani 1 1 d . . . . .
N5A N 0.4842(3) 0.1653(3) 0.58527(18) 0.0150(8) Uani 1 1 d . . . . .
N6A N 0.6209(3) 0.1022(3) 0.57665(19) 0.0167(9) Uani 1 1 d . . . . .
C1A C 0.6370(3) 0.1310(3) 0.6283(2) 0.0156(10) Uani 1 1 d . . . . .
C2A C 0.7009(3) 0.1045(3) 0.6686(2) 0.0156(10) Uani 1 1 d . . . . .
C3A C 0.7765(3) 0.0595(3) 0.6625(2) 0.0159(10) Uani 1 1 d . . . . .
H3AA H 0.793689 0.038428 0.627786 0.019 Uiso 1 1 calc R U . . .
C4A C 0.8257(3) 0.0469(3) 0.7098(2) 0.0175(10) Uani 1 1 d . . . . .
C5A C 0.7971(3) 0.0720(4) 0.7627(2) 0.0183(11) Uani 1 1 d . . . . .
C6A C 0.7197(3) 0.1142(3) 0.7697(2) 0.0175(11) Uani 1 1 d . . . . .
H6AA H 0.699911 0.129187 0.805013 0.021 Uiso 1 1 calc R U . . .
C7A C 0.6736(3) 0.1331(3) 0.7223(2) 0.0145(10) Uani 1 1 d . . . . .
C8A C 0.5926(3) 0.1793(3) 0.7145(2) 0.0152(10) Uani 1 1 d . . . . .
C9A C 0.4547(3) 0.2155(3) 0.7287(2) 0.0155(10) Uani 1 1 d . . . . .
C10A C 0.3713(3) 0.2020(3) 0.7550(2) 0.0159(10) Uani 1 1 d . . . . .
C11A C 0.3475(3) 0.1929(3) 0.8104(2) 0.0188(11) Uani 1 1 d . . . . .
H11A H 0.385574 0.202823 0.839250 0.023 Uiso 1 1 calc R U . . .
C12A C 0.2640(4) 0.1681(3) 0.8213(2) 0.0212(11) Uani 1 1 d . . . . .
C13A C 0.2085(3) 0.1509(3) 0.7777(3) 0.0225(12) Uani 1 1 d . . . . .
C14A C 0.2312(3) 0.1608(3) 0.7224(2) 0.0197(11) Uani 1 1 d . . . . .
H14A H 0.193174 0.149751 0.693641 0.024 Uiso 1 1 calc R U . . .
C15A C 0.3137(3) 0.1881(3) 0.7113(2) 0.0160(10) Uani 1 1 d . . . . .
C16A C 0.3591(3) 0.1934(3) 0.6588(2) 0.0161(10) Uani 1 1 d . . . . .
C17A C 0.4035(3) 0.1414(3) 0.5746(2) 0.0146(10) Uani 1 1 d . . . . .
C18A C 0.4070(3) 0.0801(3) 0.5276(2) 0.0171(10) Uani 1 1 d . . . . .
C19A C 0.3446(3) 0.0347(3) 0.4998(2) 0.0207(11) Uani 1 1 d . . . . .
H19A H 0.288183 0.042228 0.509283 0.025 Uiso 1 1 calc R U . . .
C20A C 0.3678(3) -0.0225(3) 0.4574(2) 0.0199(10) Uani 1 1 d . . . . .
C21A C 0.4538(3) -0.0323(3) 0.4425(2) 0.0197(11) Uani 1 1 d . . . . .
C22A C 0.5174(3) 0.0086(3) 0.4723(2) 0.0196(11) Uani 1 1 d . . . . .
H22A H 0.573857 -0.001335 0.463724 0.024 Uiso 1 1 calc R U . . .
C23A C 0.4941(3) 0.0653(3) 0.5159(2) 0.0161(9) Uani 1 1 d . . . . .
C24A C 0.5429(3) 0.1150(3) 0.5573(2) 0.0166(10) Uani 1 1 d . . . . .
C25A C 0.4946(3) 0.3789(3) 0.5861(2) 0.0153(10) Uani 1 1 d . . . . .
C26A C 0.4309(3) 0.3602(3) 0.5482(2) 0.0184(11) Uani 1 1 d . . . . .
H26A H 0.414385 0.302196 0.541336 0.022 Uiso 1 1 calc R U . . .
C27A C 0.3920(3) 0.4313(3) 0.5203(2) 0.0190(10) Uani 1 1 d . . . . .
C28A C 0.4159(3) 0.5171(3) 0.5295(2) 0.0247(12) Uani 1 1 d . . . . .
H28A H 0.388221 0.563340 0.511612 0.030 Uiso 1 1 calc R U . . .
C29A C 0.4818(4) 0.5340(4) 0.5660(3) 0.0261(13) Uani 1 1 d . . . . .
H29A H 0.500021 0.591869 0.571342 0.031 Uiso 1 1 calc R U . . .
C30A C 0.5210(3) 0.4657(3) 0.5946(2) 0.0191(11) Uani 1 1 d . . . . .
H30A H 0.564601 0.477805 0.619431 0.023 Uiso 1 1 calc R U . . .
B1A B 0.5087(4) 0.2288(4) 0.6305(2) 0.0161(11) Uani 1 1 d . . . . .
I1B I 0.20297(2) 0.65310(3) 0.51508(2) 0.03114(10) Uani 1 1 d . . . . .
Cl1B Cl -0.42316(8) 0.25029(10) 0.24282(6) 0.0299(3) Uani 1 1 d . . . . .
Cl2B Cl -0.33997(10) 0.31756(12) 0.13247(6) 0.0378(4) Uani 1 1 d . . . . .
Cl3B Cl 0.29196(9) 0.39029(11) 0.11085(7) 0.0351(3) Uani 1 1 d . . . . .
Cl4B Cl 0.40506(9) 0.34890(10) 0.21564(7) 0.0316(3) Uani 1 1 d . . . . .
Cl5B Cl 0.14248(10) 0.14146(10) 0.57216(7) 0.0336(3) Uani 1 1 d . . . . .
Cl6B Cl -0.05290(9) 0.12676(9) 0.58774(6) 0.0292(3) Uani 1 1 d . . . . .
O1B O -0.0403(2) 0.5560(2) 0.36461(17) 0.0241(8) Uani 1 1 d . . . . .
N1B N -0.0897(3) 0.4279(3) 0.31833(19) 0.0189(9) Uani 1 1 d . . . . .
N2B N -0.0224(3) 0.4433(3) 0.22998(19) 0.0196(9) Uani 1 1 d . . . . .
N3B N 0.0571(3) 0.4544(3) 0.31439(19) 0.0188(9) Uani 1 1 d . . . . .
N4B N 0.1424(3) 0.3865(3) 0.3840(2) 0.0200(9) Uani 1 1 d . . . . .
N5B N -0.0063(3) 0.4014(3) 0.39688(19) 0.0184(9) Uani 1 1 d . . . . .
N6B N -0.1462(3) 0.3443(3) 0.39354(19) 0.0201(9) Uani 1 1 d . . . . .
C1B C -0.1529(3) 0.3793(3) 0.3419(2) 0.0192(11) Uani 1 1 d . . . . .
C2B C -0.2117(3) 0.3591(4) 0.2967(2) 0.0214(11) Uani 1 1 d . . . . .
C3B C -0.2893(3) 0.3170(3) 0.2967(2) 0.0185(11) Uani 1 1 d . . . . .
H3BA H -0.314190 0.297812 0.329749 0.022 Uiso 1 1 calc R U . . .
C4B C -0.3283(3) 0.3046(4) 0.2454(2) 0.0227(11) Uani 1 1 d . . . . .
C5B C -0.2893(4) 0.3318(4) 0.1946(2) 0.0225(12) Uani 1 1 d . . . . .
C6B C -0.2107(3) 0.3722(4) 0.1955(2) 0.0205(11) Uani 1 1 d . . . . .
H6BA H -0.184412 0.388826 0.162440 0.025 Uiso 1 1 calc R U . . .
C7B C -0.1723(3) 0.3872(3) 0.2464(2) 0.0197(11) Uani 1 1 d . . . . .
C8B C -0.0912(3) 0.4270(3) 0.2618(2) 0.0196(11) Uani 1 1 d . . . . .
C9B C 0.0510(3) 0.4515(3) 0.2568(2) 0.0183(10) Uani 1 1 d . . . . .
C10B C 0.1368(3) 0.4360(3) 0.2375(2) 0.0189(11) Uani 1 1 d . . . . .
C11B C 0.1688(4) 0.4272(3) 0.1833(2) 0.0215(11) Uani 1 1 d . . . . .
H11B H 0.135085 0.438318 0.152342 0.026 Uiso 1 1 calc R U . . .
C12B C 0.2509(4) 0.4019(3) 0.1772(2) 0.0214(11) Uani 1 1 d . . . . .
C13B C 0.3022(3) 0.3836(4) 0.2247(3) 0.0240(12) Uani 1 1 d . . . . .
C14B C 0.2709(3) 0.3925(3) 0.2779(2) 0.0186(11) Uani 1 1 d . . . . .
H14B H 0.304607 0.381403 0.308911 0.022 Uiso 1 1 calc R U . . .
C15B C 0.1879(3) 0.4184(3) 0.2839(3) 0.0198(11) Uani 1 1 d . . . . .
C16B C 0.1330(3) 0.4238(3) 0.3334(2) 0.0192(11) Uani 1 1 d . . . . .
C17B C 0.0718(3) 0.3709(4) 0.4140(2) 0.0201(11) Uani 1 1 d . . . . .
C18B C 0.0564(3) 0.3083(3) 0.4574(2) 0.0189(10) Uani 1 1 d . . . . .
C19B C 0.1105(4) 0.2581(3) 0.4923(2) 0.0218(11) Uani 1 1 d . . . . .
H19B H 0.168771 0.263049 0.489070 0.026 Uiso 1 1 calc R U . . .
C20B C 0.0761(4) 0.2032(4) 0.5301(2) 0.0246(12) Uani 1 1 d . . . . .
C21B C -0.0132(3) 0.1943(3) 0.5361(2) 0.0221(11) Uani 1 1 d . . . . .
C22B C -0.0656(3) 0.2386(3) 0.5009(2) 0.0190(11) Uani 1 1 d . . . . .
H22B H -0.123546 0.229818 0.502892 0.023 Uiso 1 1 calc R U . . .
C23B C -0.0327(3) 0.2963(3) 0.4621(2) 0.0214(10) Uani 1 1 d . . . . .
C24B C -0.0699(3) 0.3512(3) 0.4182(2) 0.0195(10) Uani 1 1 d . . . . .
C25B C 0.0085(3) 0.6200(4) 0.3902(2) 0.0210(11) Uani 1 1 d . . . . .
C26B C 0.0723(4) 0.6030(3) 0.4285(2) 0.0222(11) Uani 1 1 d . . . . .
H26B H 0.087600 0.545283 0.437350 0.027 Uiso 1 1 calc R U . . .
C27B C 0.1128(3) 0.6747(4) 0.4532(2) 0.0201(11) Uani 1 1 d . . . . .
C28B C 0.0928(4) 0.7603(4) 0.4396(2) 0.0241(12) Uani 1 1 d . . . . .
H28B H 0.121703 0.807444 0.455643 0.029 Uiso 1 1 calc R U . . .
C29B C 0.0279(4) 0.7753(4) 0.4012(3) 0.0284(13) Uani 1 1 d . . . . .
H29B H 0.012869 0.832905 0.391828 0.034 Uiso 1 1 calc R U . . .
C30B C -0.0133(4) 0.7060(4) 0.3773(3) 0.0278(13) Uani 1 1 d . . . . .
H30B H -0.056736 0.716638 0.352079 0.033 Uiso 1 1 calc R U . . .
B1B B -0.0187(4) 0.4672(4) 0.3516(3) 0.0192(12) 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
I1A C27A 2.094(5) . ?
Cl1A C4A 1.733(5) . ?
Cl2A C5A 1.731(5) . ?
Cl3A C12A 1.723(6) . ?
Cl4A C13A 1.747(5) . ?
Cl5A C20A 1.722(5) . ?
Cl6A C21A 1.731(5) . ?
O1A C25A 1.366(6) . ?
O1A B1A 1.430(7) . ?
N1A C8A 1.360(7) . ?
N1A C1A 1.370(6) . ?
N1A B1A 1.510(7) . ?
N2A C8A 1.342(7) . ?
N2A C9A 1.344(7) . ?
N3A C9A 1.366(6) . ?
N3A C16A 1.371(6) . ?
N3A B1A 1.504(7) . ?
N4A C16A 1.330(7) . ?
N4A C17A 1.336(7) . ?
N5A C17A 1.355(6) . ?
N5A C24A 1.377(6) . ?
N5A B1A 1.499(7) . ?
N6A C24A 1.335(7) . ?
N6A C1A 1.335(7) . ?
C1A C2A 1.456(7) . ?
C2A C3A 1.386(7) . ?
C2A C7A 1.424(8) . ?
C3A C4A 1.389(8) . ?
C3A H3AA 0.9300 . ?
C4A C5A 1.398(8) . ?
C5A C6A 1.394(8) . ?
C6A C7A 1.380(7) . ?
C6A H6AA 0.9300 . ?
C7A C8A 1.473(7) . ?
C9A C10A 1.480(7) . ?
C10A C11A 1.384(7) . ?
C10A C15A 1.406(7) . ?
C11A C12A 1.401(8) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.388(9) . ?
C13A C14A 1.382(8) . ?
C14A C15A 1.396(7) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.451(7) . ?
C17A C18A 1.459(7) . ?
C18A C19A 1.377(7) . ?
C18A C23A 1.427(7) . ?
C19A C20A 1.383(7) . ?
C19A H19A 0.9300 . ?
C20A C21A 1.417(7) . ?
C21A C22A 1.382(8) . ?
C22A C23A 1.400(7) . ?
C22A H22A 0.9300 . ?
C23A C24A 1.465(7) . ?
C25A C26A 1.388(7) . ?
C25A C30A 1.392(7) . ?
C26A C27A 1.408(7) . ?
C26A H26A 0.9300 . ?
C27A C28A 1.369(8) . ?
C28A C29A 1.387(8) . ?
C28A H28A 0.9300 . ?
C29A C30A 1.386(7) . ?
C29A H29A 0.9300 . ?
C30A H30A 0.9300 . ?
I1B C27B 2.084(5) . ?
Cl1B C4B 1.715(6) . ?
Cl2B C5B 1.704(6) . ?
Cl3B C12B 1.726(6) . ?
Cl4B C13B 1.727(5) . ?
Cl5B C20B 1.729(6) . ?
Cl6B C21B 1.722(6) . ?
O1B C25B 1.382(6) . ?
O1B B1B 1.421(7) . ?
N1B C8B 1.354(7) . ?
N1B C1B 1.365(7) . ?
N1B B1B 1.502(7) . ?
N2B C9B 1.335(7) . ?
N2B C8B 1.353(7) . ?
N3B C16B 1.368(7) . ?
N3B C9B 1.382(7) . ?
N3B B1B 1.509(7) . ?
N4B C16B 1.343(7) . ?
N4B C17B 1.352(7) . ?
N5B C24B 1.361(7) . ?
N5B C17B 1.384(7) . ?
N5B B1B 1.484(8) . ?
N6B C1B 1.349(7) . ?
N6B C24B 1.351(7) . ?
C1B C2B 1.461(8) . ?
C2B C3B 1.385(7) . ?
C2B C7B 1.422(8) . ?
C3B C4B 1.389(8) . ?
C3B H3BA 0.9300 . ?
C4B C5B 1.424(8) . ?
C5B C6B 1.388(8) . ?
C6B C7B 1.381(8) . ?
C6B H6BA 0.9300 . ?
C7B C8B 1.467(8) . ?
C9B C10B 1.455(7) . ?
C10B C11B 1.400(8) . ?
C10B C15B 1.400(8) . ?
C11B C12B 1.365(8) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.424(9) . ?
C13B C14B 1.374(9) . ?
C14B C15B 1.381(7) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.473(8) . ?
C17B C18B 1.426(8) . ?
C18B C19B 1.418(8) . ?
C18B C23B 1.429(7) . ?
C19B C20B 1.345(8) . ?
C19B H19B 0.9300 . ?
C20B C21B 1.430(8) . ?
C21B C22B 1.360(8) . ?
C22B C23B 1.376(8) . ?
C22B H22B 0.9300 . ?
C23B C24B 1.464(8) . ?
C25B C30B 1.380(8) . ?
C25B C26B 1.390(8) . ?
C26B C27B 1.392(7) . ?
C26B H26B 0.9300 . ?
C27B C28B 1.372(8) . ?
C28B C29B 1.399(8) . ?
C28B H28B 0.9300 . ?
C29B C30B 1.361(8) . ?
C29B H29B 0.9300 . ?
C30B H30B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25A O1A B1A 128.2(4) . . ?
C8A N1A C1A 114.8(4) . . ?
C8A N1A B1A 123.1(4) . . ?
C1A N1A B1A 121.7(4) . . ?
C8A N2A C9A 116.2(4) . . ?
C9A N3A C16A 113.0(4) . . ?
C9A N3A B1A 122.0(4) . . ?
C16A N3A B1A 122.8(4) . . ?
C16A N4A C17A 117.2(4) . . ?
C17A N5A C24A 113.6(4) . . ?
C17A N5A B1A 123.5(4) . . ?
C24A N5A B1A 122.0(4) . . ?
C24A N6A C1A 116.8(4) . . ?
N6A C1A N1A 123.1(4) . . ?
N6A C1A C2A 131.1(5) . . ?
N1A C1A C2A 104.7(4) . . ?
C3A C2A C7A 120.5(5) . . ?
C3A C2A C1A 131.8(5) . . ?
C7A C2A C1A 107.7(4) . . ?
C2A C3A C4A 117.8(5) . . ?
C2A C3A H3AA 121.1 . . ?
C4A C3A H3AA 121.1 . . ?
C3A C4A C5A 121.3(5) . . ?
C3A C4A Cl1A 118.9(4) . . ?
C5A C4A Cl1A 119.8(4) . . ?
C6A C5A C4A 121.3(5) . . ?
C6A C5A Cl2A 118.9(5) . . ?
C4A C5A Cl2A 119.8(4) . . ?
C7A C6A C5A 117.6(5) . . ?
C7A C6A H6AA 121.2 . . ?
C5A C6A H6AA 121.2 . . ?
C6A C7A C2A 121.2(5) . . ?
C6A C7A C8A 131.7(5) . . ?
C2A C7A C8A 107.1(4) . . ?
N2A C8A N1A 122.9(4) . . ?
N2A C8A C7A 131.5(5) . . ?
N1A C8A C7A 104.5(4) . . ?
N2A C9A N3A 124.0(4) . . ?
N2A C9A C10A 128.3(4) . . ?
N3A C9A C10A 105.2(4) . . ?
C11A C10A C15A 121.4(5) . . ?
C11A C10A C9A 131.7(5) . . ?
C15A C10A C9A 106.6(4) . . ?
C10A C11A C12A 117.5(5) . . ?
C10A C11A H11A 121.2 . . ?
C12A C11A H11A 121.2 . . ?
C13A C12A C11A 120.6(5) . . ?
C13A C12A Cl3A 121.4(4) . . ?
C11A C12A Cl3A 118.0(4) . . ?
C14A C13A C12A 122.3(5) . . ?
C14A C13A Cl4A 117.6(4) . . ?
C12A C13A Cl4A 120.0(4) . . ?
C13A C14A C15A 117.3(5) . . ?
C13A C14A H14A 121.4 . . ?
C15A C14A H14A 121.4 . . ?
C14A C15A C10A 120.8(5) . . ?
C14A C15A C16A 130.3(5) . . ?
C10A C15A C16A 108.3(4) . . ?
N4A C16A N3A 123.1(5) . . ?
N4A C16A C15A 129.4(5) . . ?
N3A C16A C15A 105.4(4) . . ?
N4A C17A N5A 123.0(5) . . ?
N4A C17A C18A 129.6(5) . . ?
N5A C17A C18A 106.1(4) . . ?
C19A C18A C23A 121.5(5) . . ?
C19A C18A C17A 131.4(5) . . ?
C23A C18A C17A 106.8(4) . . ?
C18A C19A C20A 118.4(5) . . ?
C18A C19A H19A 120.8 . . ?
C20A C19A H19A 120.8 . . ?
C19A C20A C21A 120.5(5) . . ?
C19A C20A Cl5A 119.1(4) . . ?
C21A C20A Cl5A 120.5(4) . . ?
C22A C21A C20A 121.7(5) . . ?
C22A C21A Cl6A 119.1(4) . . ?
C20A C21A Cl6A 119.2(4) . . ?
C21A C22A C23A 117.7(5) . . ?
C21A C22A H22A 121.1 . . ?
C23A C22A H22A 121.1 . . ?
C22A C23A C18A 119.9(5) . . ?
C22A C23A C24A 132.7(5) . . ?
C18A C23A C24A 107.3(4) . . ?
N6A C24A N5A 122.5(5) . . ?
N6A C24A C23A 130.6(5) . . ?
N5A C24A C23A 104.8(4) . . ?
O1A C25A C26A 123.7(4) . . ?
O1A C25A C30A 115.9(4) . . ?
C26A C25A C30A 120.4(5) . . ?
C25A C26A C27A 118.3(5) . . ?
C25A C26A H26A 120.8 . . ?
C27A C26A H26A 120.8 . . ?
C28A C27A C26A 121.7(5) . . ?
C28A C27A I1A 119.2(4) . . ?
C26A C27A I1A 119.1(4) . . ?
C27A C28A C29A 119.0(5) . . ?
C27A C28A H28A 120.5 . . ?
C29A C28A H28A 120.5 . . ?
C30A C29A C28A 120.8(5) . . ?
C30A C29A H29A 119.6 . . ?
C28A C29A H29A 119.6 . . ?
C29A C30A C25A 119.7(5) . . ?
C29A C30A H30A 120.1 . . ?
C25A C30A H30A 120.1 . . ?
O1A B1A N5A 119.4(5) . . ?
O1A B1A N3A 118.2(4) . . ?
N5A B1A N3A 103.9(4) . . ?
O1A B1A N1A 107.3(4) . . ?
N5A B1A N1A 102.5(4) . . ?
N3A B1A N1A 103.4(4) . . ?
C25B O1B B1B 128.6(4) . . ?
C8B N1B C1B 113.3(5) . . ?
C8B N1B B1B 123.1(5) . . ?
C1B N1B B1B 123.0(5) . . ?
C9B N2B C8B 116.7(5) . . ?
C16B N3B C9B 112.5(4) . . ?
C16B N3B B1B 123.3(5) . . ?
C9B N3B B1B 122.4(4) . . ?
C16B N4B C17B 117.4(5) . . ?
C24B N5B C17B 111.5(4) . . ?
C24B N5B B1B 123.3(5) . . ?
C17B N5B B1B 123.9(5) . . ?
C1B N6B C24B 116.2(5) . . ?
N6B C1B N1B 122.2(5) . . ?
N6B C1B C2B 130.4(5) . . ?
N1B C1B C2B 105.9(5) . . ?
C3B C2B C7B 121.9(5) . . ?
C3B C2B C1B 131.5(5) . . ?
C7B C2B C1B 106.5(5) . . ?
C2B C3B C4B 117.2(5) . . ?
C2B C3B H3BA 121.4 . . ?
C4B C3B H3BA 121.4 . . ?
C3B C4B C5B 121.5(5) . . ?
C3B C4B Cl1B 119.2(4) . . ?
C5B C4B Cl1B 119.2(4) . . ?
C6B C5B C4B 120.2(5) . . ?
C6B C5B Cl2B 119.5(5) . . ?
C4B C5B Cl2B 120.3(4) . . ?
C7B C6B C5B 118.9(5) . . ?
C7B C6B H6BA 120.6 . . ?
C5B C6B H6BA 120.6 . . ?
C6B C7B C2B 120.2(5) . . ?
C6B C7B C8B 132.6(5) . . ?
C2B C7B C8B 107.2(5) . . ?
N2B C8B N1B 123.2(5) . . ?
N2B C8B C7B 129.8(5) . . ?
N1B C8B C7B 105.7(5) . . ?
N2B C9B N3B 122.9(5) . . ?
N2B C9B C10B 130.3(5) . . ?
N3B C9B C10B 104.8(4) . . ?
C11B C10B C15B 120.4(5) . . ?
C11B C10B C9B 130.4(5) . . ?
C15B C10B C9B 108.7(5) . . ?
C12B C11B C10B 118.2(5) . . ?
C12B C11B H11B 120.9 . . ?
C10B C11B H11B 120.9 . . ?
C11B C12B C13B 120.9(5) . . ?
C11B C12B Cl3B 119.1(5) . . ?
C13B C12B Cl3B 119.9(4) . . ?
C14B C13B C12B 120.9(5) . . ?
C14B C13B Cl4B 119.1(5) . . ?
C12B C13B Cl4B 119.9(5) . . ?
C13B C14B C15B 117.9(5) . . ?
C13B C14B H14B 121.0 . . ?
C15B C14B H14B 121.0 . . ?
C14B C15B C10B 121.6(5) . . ?
C14B C15B C16B 131.5(5) . . ?
C10B C15B C16B 106.6(5) . . ?
N4B C16B N3B 122.6(5) . . ?
N4B C16B C15B 129.6(5) . . ?
N3B C16B C15B 105.7(5) . . ?
N4B C17B N5B 121.7(5) . . ?
N4B C17B C18B 130.1(5) . . ?
N5B C17B C18B 106.5(4) . . ?
C19B C18B C17B 132.9(5) . . ?
C19B C18B C23B 118.9(5) . . ?
C17B C18B C23B 108.1(5) . . ?
C20B C19B C18B 118.8(5) . . ?
C20B C19B H19B 120.6 . . ?
C18B C19B H19B 120.6 . . ?
C19B C20B C21B 121.9(5) . . ?
C19B C20B Cl5B 118.5(4) . . ?
C21B C20B Cl5B 119.6(4) . . ?
C22B C21B C20B 119.7(5) . . ?
C22B C21B Cl6B 121.0(4) . . ?
C20B C21B Cl6B 119.3(4) . . ?
C21B C22B C23B 119.9(5) . . ?
C21B C22B H22B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
C22B C23B C18B 120.6(5) . . ?
C22B C23B C24B 133.7(5) . . ?
C18B C23B C24B 105.6(5) . . ?
N6B C24B N5B 122.9(5) . . ?
N6B C24B C23B 129.2(5) . . ?
N5B C24B C23B 106.7(5) . . ?
C30B C25B O1B 114.8(5) . . ?
C30B C25B C26B 120.3(5) . . ?
O1B C25B C26B 124.8(5) . . ?
C25B C26B C27B 118.2(5) . . ?
C25B C26B H26B 120.9 . . ?
C27B C26B H26B 120.9 . . ?
C28B C27B C26B 121.8(5) . . ?
C28B C27B I1B 118.4(4) . . ?
C26B C27B I1B 119.8(4) . . ?
C27B C28B C29B 118.6(5) . . ?
C27B C28B H28B 120.7 . . ?
C29B C28B H28B 120.7 . . ?
C30B C29B C28B 120.3(6) . . ?
C30B C29B H29B 119.8 . . ?
C28B C29B H29B 119.8 . . ?
C29B C30B C25B 120.8(6) . . ?
C29B C30B H30B 119.6 . . ?
C25B C30B H30B 119.6 . . ?
O1B B1B N5B 120.3(5) . . ?
O1B B1B N1B 108.0(4) . . ?
N5B B1B N1B 102.8(4) . . ?
O1B B1B N3B 116.3(5) . . ?
N5B B1B N3B 103.9(4) . . ?
N1B B1B N3B 103.5(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
C24A N6A C1A N1A -9.0(7) . . . . ?
C24A N6A C1A C2A 156.9(5) . . . . ?
C8A N1A C1A N6A 157.4(5) . . . . ?
B1A N1A C1A N6A -15.4(7) . . . . ?
C8A N1A C1A C2A -11.6(5) . . . . ?
B1A N1A C1A C2A 175.5(4) . . . . ?
N6A C1A C2A C3A 19.0(9) . . . . ?
N1A C1A C2A C3A -173.2(5) . . . . ?
N6A C1A C2A C7A -160.5(5) . . . . ?
N1A C1A C2A C7A 7.3(5) . . . . ?
C7A C2A C3A C4A -2.7(7) . . . . ?
C1A C2A C3A C4A 177.8(5) . . . . ?
C2A C3A C4A C5A 5.3(7) . . . . ?
C2A C3A C4A Cl1A -172.9(4) . . . . ?
C3A C4A C5A C6A -3.0(8) . . . . ?
Cl1A C4A C5A C6A 175.2(4) . . . . ?
C3A C4A C5A Cl2A 178.2(4) . . . . ?
Cl1A C4A C5A Cl2A -3.6(6) . . . . ?
C4A C5A C6A C7A -2.1(8) . . . . ?
Cl2A C5A C6A C7A 176.7(4) . . . . ?
C5A C6A C7A C2A 4.6(7) . . . . ?
C5A C6A C7A C8A -177.3(5) . . . . ?
C3A C2A C7A C6A -2.3(7) . . . . ?
C1A C2A C7A C6A 177.3(5) . . . . ?
C3A C2A C7A C8A 179.2(4) . . . . ?
C1A C2A C7A C8A -1.2(5) . . . . ?
C9A N2A C8A N1A 7.9(7) . . . . ?
C9A N2A C8A C7A -158.3(5) . . . . ?
C1A N1A C8A N2A -158.5(4) . . . . ?
B1A N1A C8A N2A 14.2(7) . . . . ?
C1A N1A C8A C7A 10.9(5) . . . . ?
B1A N1A C8A C7A -176.4(4) . . . . ?
C6A C7A C8A N2A -15.7(9) . . . . ?
C2A C7A C8A N2A 162.6(5) . . . . ?
C6A C7A C8A N1A 176.3(5) . . . . ?
C2A C7A C8A N1A -5.4(5) . . . . ?
C8A N2A C9A N3A -8.4(7) . . . . ?
C8A N2A C9A C10A 150.8(5) . . . . ?
C16A N3A C9A N2A 150.4(5) . . . . ?
B1A N3A C9A N2A -13.3(7) . . . . ?
C16A N3A C9A C10A -12.8(5) . . . . ?
B1A N3A C9A C10A -176.5(4) . . . . ?
N2A C9A C10A C11A 18.2(9) . . . . ?
N3A C9A C10A C11A -179.6(5) . . . . ?
N2A C9A C10A C15A -154.5(5) . . . . ?
N3A C9A C10A C15A 7.7(5) . . . . ?
C15A C10A C11A C12A 0.8(7) . . . . ?
C9A C10A C11A C12A -171.0(5) . . . . ?
C10A C11A C12A C13A 1.9(7) . . . . ?
C10A C11A C12A Cl3A -179.1(4) . . . . ?
C11A C12A C13A C14A -2.7(8) . . . . ?
Cl3A C12A C13A C14A 178.2(4) . . . . ?
C11A C12A C13A Cl4A 176.0(4) . . . . ?
Cl3A C12A C13A Cl4A -3.0(6) . . . . ?
C12A C13A C14A C15A 0.8(7) . . . . ?
Cl4A C13A C14A C15A -178.0(4) . . . . ?
C13A C14A C15A C10A 1.9(7) . . . . ?
C13A C14A C15A C16A 171.2(5) . . . . ?
C11A C10A C15A C14A -2.8(7) . . . . ?
C9A C10A C15A C14A 170.9(4) . . . . ?
C11A C10A C15A C16A -174.1(4) . . . . ?
C9A C10A C15A C16A -0.5(5) . . . . ?
C17A N4A C16A N3A 8.0(7) . . . . ?
C17A N4A C16A C15A -153.1(5) . . . . ?
C9A N3A C16A N4A -152.5(5) . . . . ?
B1A N3A C16A N4A 11.1(7) . . . . ?
C9A N3A C16A C15A 12.5(5) . . . . ?
B1A N3A C16A C15A 176.0(4) . . . . ?
C14A C15A C16A N4A -13.5(9) . . . . ?
C10A C15A C16A N4A 156.8(5) . . . . ?
C14A C15A C16A N3A -177.1(5) . . . . ?
C10A C15A C16A N3A -6.9(5) . . . . ?
C16A N4A C17A N5A -7.4(7) . . . . ?
C16A N4A C17A C18A 157.7(5) . . . . ?
C24A N5A C17A N4A 157.2(5) . . . . ?
B1A N5A C17A N4A -12.4(7) . . . . ?
C24A N5A C17A C18A -11.0(5) . . . . ?
B1A N5A C17A C18A 179.4(4) . . . . ?
N4A C17A C18A C19A 12.1(9) . . . . ?
N5A C17A C18A C19A 179.2(5) . . . . ?
N4A C17A C18A C23A -162.2(5) . . . . ?
N5A C17A C18A C23A 4.9(5) . . . . ?
C23A C18A C19A C20A -3.8(8) . . . . ?
C17A C18A C19A C20A -177.4(5) . . . . ?
C18A C19A C20A C21A -1.3(8) . . . . ?
C18A C19A C20A Cl5A 178.6(4) . . . . ?
C19A C20A C21A C22A 5.5(8) . . . . ?
Cl5A C20A C21A C22A -174.4(4) . . . . ?
C19A C20A C21A Cl6A -173.8(4) . . . . ?
Cl5A C20A C21A Cl6A 6.3(6) . . . . ?
C20A C21A C22A C23A -4.3(7) . . . . ?
Cl6A C21A C22A C23A 175.0(4) . . . . ?
C21A C22A C23A C18A -0.8(7) . . . . ?
C21A C22A C23A C24A 176.3(5) . . . . ?
C19A C18A C23A C22A 5.0(8) . . . . ?
C17A C18A C23A C22A 180.0(4) . . . . ?
C19A C18A C23A C24A -172.8(5) . . . . ?
C17A C18A C23A C24A 2.2(5) . . . . ?
C1A N6A C24A N5A 8.3(7) . . . . ?
C1A N6A C24A C23A -152.5(5) . . . . ?
C17A N5A C24A N6A -152.7(5) . . . . ?
B1A N5A C24A N6A 17.0(7) . . . . ?
C17A N5A C24A C23A 12.2(5) . . . . ?
B1A N5A C24A C23A -178.0(4) . . . . ?
C22A C23A C24A N6A -22.4(9) . . . . ?
C18A C23A C24A N6A 154.9(5) . . . . ?
C22A C23A C24A N5A 174.3(5) . . . . ?
C18A C23A C24A N5A -8.3(5) . . . . ?
B1A O1A C25A C26A -24.5(8) . . . . ?
B1A O1A C25A C30A 157.4(5) . . . . ?
O1A C25A C26A C27A 179.7(5) . . . . ?
C30A C25A C26A C27A -2.2(8) . . . . ?
C25A C26A C27A C28A 0.4(8) . . . . ?
C25A C26A C27A I1A 178.9(4) . . . . ?
C26A C27A C28A C29A 2.1(9) . . . . ?
I1A C27A C28A C29A -176.4(4) . . . . ?
C27A C28A C29A C30A -2.7(9) . . . . ?
C28A C29A C30A C25A 0.9(9) . . . . ?
O1A C25A C30A C29A 179.8(5) . . . . ?
C26A C25A C30A C29A 1.6(8) . . . . ?
C25A O1A B1A N5A 58.4(7) . . . . ?
C25A O1A B1A N3A -69.5(7) . . . . ?
C25A O1A B1A N1A 174.3(4) . . . . ?
C17A N5A B1A O1A -107.8(6) . . . . ?
C24A N5A B1A O1A 83.5(6) . . . . ?
C17A N5A B1A N3A 26.5(6) . . . . ?
C24A N5A B1A N3A -142.2(4) . . . . ?
C17A N5A B1A N1A 133.9(4) . . . . ?
C24A N5A B1A N1A -34.8(6) . . . . ?
C9A N3A B1A O1A -88.7(6) . . . . ?
C16A N3A B1A O1A 109.2(5) . . . . ?
C9A N3A B1A N5A 136.4(4) . . . . ?
C16A N3A B1A N5A -25.7(6) . . . . ?
C9A N3A B1A N1A 29.6(6) . . . . ?
C16A N3A B1A N1A -132.5(4) . . . . ?
C8A N1A B1A O1A 95.2(5) . . . . ?
C1A N1A B1A O1A -92.6(5) . . . . ?
C8A N1A B1A N5A -138.2(4) . . . . ?
C1A N1A B1A N5A 34.0(6) . . . . ?
C8A N1A B1A N3A -30.4(6) . . . . ?
C1A N1A B1A N3A 141.8(4) . . . . ?
C24B N6B C1B N1B -7.4(7) . . . . ?
C24B N6B C1B C2B 156.3(5) . . . . ?
C8B N1B C1B N6B 154.7(5) . . . . ?
B1B N1B C1B N6B -16.9(8) . . . . ?
C8B N1B C1B C2B -12.4(6) . . . . ?
B1B N1B C1B C2B 176.0(5) . . . . ?
N6B C1B C2B C3B 19.1(9) . . . . ?
N1B C1B C2B C3B -175.3(5) . . . . ?
N6B C1B C2B C7B -157.4(5) . . . . ?
N1B C1B C2B C7B 8.3(5) . . . . ?
C7B C2B C3B C4B -1.2(8) . . . . ?
C1B C2B C3B C4B -177.2(5) . . . . ?
C2B C3B C4B C5B 1.7(8) . . . . ?
C2B C3B C4B Cl1B 178.3(4) . . . . ?
C3B C4B C5B C6B -0.4(8) . . . . ?
Cl1B C4B C5B C6B -177.0(4) . . . . ?
C3B C4B C5B Cl2B -178.7(4) . . . . ?
Cl1B C4B C5B Cl2B 4.7(7) . . . . ?
C4B C5B C6B C7B -1.5(8) . . . . ?
Cl2B C5B C6B C7B 176.8(4) . . . . ?
C5B C6B C7B C2B 1.9(8) . . . . ?
C5B C6B C7B C8B 179.6(5) . . . . ?
C3B C2B C7B C6B -0.6(8) . . . . ?
C1B C2B C7B C6B 176.3(5) . . . . ?
C3B C2B C7B C8B -178.8(5) . . . . ?
C1B C2B C7B C8B -1.9(6) . . . . ?
C9B N2B C8B N1B 6.8(7) . . . . ?
C9B N2B C8B C7B -157.8(5) . . . . ?
C1B N1B C8B N2B -156.7(5) . . . . ?
B1B N1B C8B N2B 14.9(8) . . . . ?
C1B N1B C8B C7B 11.1(6) . . . . ?
B1B N1B C8B C7B -177.3(5) . . . . ?
C6B C7B C8B N2B -16.3(10) . . . . ?
C2B C7B C8B N2B 161.6(5) . . . . ?
C6B C7B C8B N1B 176.9(6) . . . . ?
C2B C7B C8B N1B -5.1(6) . . . . ?
C8B N2B C9B N3B -7.7(7) . . . . ?
C8B N2B C9B C10B 154.1(5) . . . . ?
C16B N3B C9B N2B 152.5(5) . . . . ?
B1B N3B C9B N2B -12.8(8) . . . . ?
C16B N3B C9B C10B -13.2(6) . . . . ?
B1B N3B C9B C10B -178.5(4) . . . . ?
N2B C9B C10B C11B 15.9(9) . . . . ?
N3B C9B C10B C11B -179.9(5) . . . . ?
N2B C9B C10B C15B -156.3(5) . . . . ?
N3B C9B C10B C15B 8.0(5) . . . . ?
C15B C10B C11B C12B -0.6(8) . . . . ?
C9B C10B C11B C12B -171.9(5) . . . . ?
C10B C11B C12B C13B 1.0(8) . . . . ?
C10B C11B C12B Cl3B 179.9(4) . . . . ?
C11B C12B C13B C14B -1.2(8) . . . . ?
Cl3B C12B C13B C14B 179.9(4) . . . . ?
C11B C12B C13B Cl4B 178.3(4) . . . . ?
Cl3B C12B C13B Cl4B -0.6(6) . . . . ?
C12B C13B C14B C15B 0.9(8) . . . . ?
Cl4B C13B C14B C15B -178.6(4) . . . . ?
C13B C14B C15B C10B -0.5(8) . . . . ?
C13B C14B C15B C16B 171.7(5) . . . . ?
C11B C10B C15B C14B 0.3(8) . . . . ?
C9B C10B C15B C14B 173.4(5) . . . . ?
C11B C10B C15B C16B -173.6(5) . . . . ?
C9B C10B C15B C16B -0.5(6) . . . . ?
C17B N4B C16B N3B 7.2(8) . . . . ?
C17B N4B C16B C15B -154.0(5) . . . . ?
C9B N3B C16B N4B -152.0(5) . . . . ?
B1B N3B C16B N4B 13.2(8) . . . . ?
C9B N3B C16B C15B 13.0(6) . . . . ?
B1B N3B C16B C15B 178.2(4) . . . . ?
C14B C15B C16B N4B -16.8(10) . . . . ?
C10B C15B C16B N4B 156.3(5) . . . . ?
C14B C15B C16B N3B 179.7(5) . . . . ?
C10B C15B C16B N3B -7.3(5) . . . . ?
C16B N4B C17B N5B -7.7(7) . . . . ?
C16B N4B C17B C18B 155.7(5) . . . . ?
C24B N5B C17B N4B 155.1(5) . . . . ?
B1B N5B C17B N4B -12.3(8) . . . . ?
C24B N5B C17B C18B -11.8(6) . . . . ?
B1B N5B C17B C18B -179.2(4) . . . . ?
N4B C17B C18B C19B 17.6(10) . . . . ?
N5B C17B C18B C19B -177.1(5) . . . . ?
N4B C17B C18B C23B -160.1(5) . . . . ?
N5B C17B C18B C23B 5.2(6) . . . . ?
C17B C18B C19B C20B -179.9(5) . . . . ?
C23B C18B C19B C20B -2.4(7) . . . . ?
C18B C19B C20B C21B -0.1(8) . . . . ?
C18B C19B C20B Cl5B 179.5(4) . . . . ?
C19B C20B C21B C22B 3.6(8) . . . . ?
Cl5B C20B C21B C22B -175.9(4) . . . . ?
C19B C20B C21B Cl6B -176.9(4) . . . . ?
Cl5B C20B C21B Cl6B 3.5(6) . . . . ?
C20B C21B C22B C23B -4.5(8) . . . . ?
Cl6B C21B C22B C23B 176.1(4) . . . . ?
C21B C22B C23B C18B 1.9(8) . . . . ?
C21B C22B C23B C24B 178.1(5) . . . . ?
C19B C18B C23B C22B 1.5(7) . . . . ?
C17B C18B C23B C22B 179.6(5) . . . . ?
C19B C18B C23B C24B -175.6(5) . . . . ?
C17B C18B C23B C24B 2.5(6) . . . . ?
C1B N6B C24B N5B 9.6(7) . . . . ?
C1B N6B C24B C23B -155.7(5) . . . . ?
C17B N5B C24B N6B -154.8(5) . . . . ?
B1B N5B C24B N6B 12.7(8) . . . . ?
C17B N5B C24B C23B 13.3(6) . . . . ?
B1B N5B C24B C23B -179.2(5) . . . . ?
C22B C23B C24B N6B -18.9(10) . . . . ?
C18B C23B C24B N6B 157.7(5) . . . . ?
C22B C23B C24B N5B 174.0(5) . . . . ?
C18B C23B C24B N5B -9.4(6) . . . . ?
B1B O1B C25B C30B 154.5(5) . . . . ?
B1B O1B C25B C26B -28.9(9) . . . . ?
C30B C25B C26B C27B 0.2(8) . . . . ?
O1B C25B C26B C27B -176.3(5) . . . . ?
C25B C26B C27B C28B -1.8(8) . . . . ?
C25B C26B C27B I1B 175.7(4) . . . . ?
C26B C27B C28B C29B 2.1(8) . . . . ?
I1B C27B C28B C29B -175.3(4) . . . . ?
C27B C28B C29B C30B -0.9(9) . . . . ?
C28B C29B C30B C25B -0.6(9) . . . . ?
O1B C25B C30B C29B 177.8(5) . . . . ?
C26B C25B C30B C29B 1.0(9) . . . . ?
C25B O1B B1B N5B 68.8(7) . . . . ?
C25B O1B B1B N1B -173.8(5) . . . . ?
C25B O1B B1B N3B -58.0(8) . . . . ?
C24B N5B B1B O1B 89.1(6) . . . . ?
C17B N5B B1B O1B -104.9(6) . . . . ?
C24B N5B B1B N1B -30.9(6) . . . . ?
C17B N5B B1B N1B 135.1(5) . . . . ?
C24B N5B B1B N3B -138.5(5) . . . . ?
C17B N5B B1B N3B 27.4(6) . . . . ?
C8B N1B B1B O1B 94.0(6) . . . . ?
C1B N1B B1B O1B -95.2(6) . . . . ?
C8B N1B B1B N5B -137.8(5) . . . . ?
C1B N1B B1B N5B 33.0(6) . . . . ?
C8B N1B B1B N3B -29.9(7) . . . . ?
C1B N1B B1B N3B 140.9(5) . . . . ?
C16B N3B B1B O1B 106.7(6) . . . . ?
C9B N3B B1B O1B -89.5(6) . . . . ?
C16B N3B B1B N5B -27.8(6) . . . . ?
C9B N3B B1B N5B 135.9(5) . . . . ?
C16B N3B B1B N1B -135.0(5) . . . . ?
C9B N3B B1B N1B 28.8(6) . . . . ?

_refine_diff_density_max         0.808
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.084


