# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2376336'
loop_
_audit_author_name
_audit_author_address
'Paul D. Boyle'
;The University of Western Ontario
Canada
;
_audit_update_record             
;
2024-08-07 deposited with the CCDC.	2024-12-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 B N4 O'
_chemical_formula_weight         416.28
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'

_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                   9.804(5)
_cell_length_b                   16.350(11)
_cell_length_c                   13.564(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.989(15)
_cell_angle_gamma                90
_cell_volume                     2056(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    7196
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      32.69
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.169
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9008
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64034
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.018
_diffrn_reflns_theta_max         35.735
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9508
_reflns_number_gt                6835
_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
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    Mercury
_computing_publication_material  cif2tables.py
_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)+(0.0677P)²+0.3434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9508
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
B1 B 0.75878(11) 0.74821(6) 0.67435(8) 0.01279(17) Uani 1 1 d . . . . .
N1 N 0.85440(8) 0.82265(5) 0.71768(6) 0.01273(14) Uani 1 1 d . . . . .
N2 N 0.86044(9) 0.85019(5) 0.81541(6) 0.01314(14) Uani 1 1 d . . . . .
N3 N 0.60154(8) 0.78585(5) 0.66898(6) 0.01320(14) Uani 1 1 d . . . . .
N4 N 0.76255(9) 0.72590(5) 0.56825(6) 0.01491(15) Uani 1 1 d . . . . .
C1 C 0.73886(10) 0.84707(5) 0.83478(7) 0.01226(15) Uani 1 1 d . . . . .
C2 C 0.59950(10) 0.83117(6) 0.75249(7) 0.01293(15) Uani 1 1 d . . . . .
C3 C 0.48331(11) 0.78041(6) 0.58418(8) 0.01698(17) Uani 1 1 d . . . . .
H3 H 0.4917(15) 0.7499(8) 0.5252(11) 0.019(3) Uiso 1 1 d . . . . .
C4 C 0.35561(11) 0.81883(7) 0.57983(8) 0.01972(19) Uani 1 1 d . . . . .
H4 H 0.2738(17) 0.8145(9) 0.5168(12) 0.030(4) Uiso 1 1 d . . . . .
C5 C 0.34975(11) 0.86371(7) 0.66495(8) 0.01916(19) Uani 1 1 d . . . . .
H5 H 0.2622(16) 0.8912(9) 0.6642(11) 0.025(4) Uiso 1 1 d . . . . .
C6 C 0.47295(10) 0.87061(6) 0.75137(8) 0.01653(17) Uani 1 1 d . . . . .
H6 H 0.4720(16) 0.9042(9) 0.8118(12) 0.025(4) Uiso 1 1 d . . . . .
C7 C 0.73947(10) 0.87528(6) 0.93867(7) 0.01281(15) Uani 1 1 d . . . . .
C8 C 0.64075(11) 0.84479(7) 0.98415(8) 0.01728(17) Uani 1 1 d . . . . .
H8 H 0.5718(16) 0.8033(9) 0.9484(11) 0.026(4) Uiso 1 1 d . . . . .
C9 C 0.63966(12) 0.87458(7) 1.08000(8) 0.0215(2) Uani 1 1 d . . . . .
H9 H 0.5686(17) 0.8538(10) 1.1115(13) 0.034(4) Uiso 1 1 d . . . . .
C10 C 0.73764(12) 0.93416(7) 1.13158(8) 0.0207(2) Uani 1 1 d . . . . .
H10 H 0.7371(16) 0.9569(9) 1.1995(12) 0.028(4) Uiso 1 1 d . . . . .
C11 C 0.83926(12) 0.96328(6) 1.08851(8) 0.01811(18) Uani 1 1 d . . . . .
H11 H 0.9075(15) 1.0058(9) 1.1259(11) 0.024(4) Uiso 1 1 d . . . . .
C12 C 0.83950(11) 0.93429(6) 0.99223(7) 0.01529(16) Uani 1 1 d . . . . .
H12 H 0.9092(15) 0.9571(8) 0.9597(10) 0.018(3) Uiso 1 1 d . . . . .
C13 C 0.94861(10) 0.85877(5) 0.67504(7) 0.01227(15) Uani 1 1 d . . . . .
O1 O 1.04484(8) 0.90645(4) 0.72281(6) 0.01741(14) Uani 1 1 d . . . . .
C14 C 0.91579(10) 0.84069(6) 0.56305(7) 0.01243(15) Uani 1 1 d . . . . .
C15 C 0.97393(11) 0.89277(6) 0.50560(8) 0.01589(17) Uani 1 1 d . . . . .
H15 H 1.0372(15) 0.9376(8) 0.5415(10) 0.018(3) Uiso 1 1 d . . . . .
C16 C 0.94483(12) 0.88196(7) 0.39963(8) 0.02006(19) Uani 1 1 d . . . . .
H16 H 0.9842(16) 0.9204(9) 0.3603(11) 0.025(4) Uiso 1 1 d . . . . .
C17 C 0.86130(12) 0.81524(7) 0.35109(8) 0.01874(18) Uani 1 1 d . . . . .
H17 H 0.8411(16) 0.8056(9) 0.2759(11) 0.022(3) Uiso 1 1 d . . . . .
C18 C 0.80298(10) 0.76229(6) 0.40609(7) 0.01566(17) Uani 1 1 d . . . . .
H18 H 0.7432(15) 0.7168(9) 0.3711(11) 0.021(3) Uiso 1 1 d . . . . .
C19 C 0.82405(10) 0.77556(6) 0.51299(7) 0.01256(15) Uani 1 1 d . . . . .
C20 C 0.79969(10) 0.67240(6) 0.75446(7) 0.01365(16) Uani 1 1 d . . . . .
C21 C 0.70033(11) 0.61690(6) 0.76928(9) 0.01881(18) Uani 1 1 d . . . . .
H21 H 0.5942(17) 0.6278(9) 0.7380(12) 0.027(4) Uiso 1 1 d . . . . .
C22 C 0.74393(13) 0.54512(7) 0.82649(10) 0.0234(2) Uani 1 1 d . . . . .
H22 H 0.6725(17) 0.5064(10) 0.8381(12) 0.034(4) Uiso 1 1 d . . . . .
C23 C 0.88892(13) 0.52796(7) 0.87167(9) 0.0235(2) Uani 1 1 d . . . . .
H23 H 0.9237(16) 0.4770(10) 0.9117(12) 0.028(4) Uiso 1 1 d . . . . .
C24 C 0.99106(12) 0.58294(7) 0.86043(9) 0.0235(2) Uani 1 1 d . . . . .
H24 H 1.0925(18) 0.5714(10) 0.8926(12) 0.035(4) Uiso 1 1 d . . . . .
C25 C 0.94629(11) 0.65386(7) 0.80262(8) 0.01886(18) Uani 1 1 d . . . . .
H25 H 1.0212(16) 0.6941(9) 0.7943(11) 0.023(3) Uiso 1 1 d . . . . .
C26 C 0.70534(13) 0.64738(7) 0.52118(9) 0.0205(2) Uani 1 1 d . . . . .
H26A H 0.6761(17) 0.6149(10) 0.5715(12) 0.032(4) Uiso 1 1 d . . . . .
H26B H 0.7786(16) 0.6168(9) 0.5038(12) 0.026(4) Uiso 1 1 d . . . . .
H26C H 0.6175(17) 0.6544(10) 0.4576(12) 0.028(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N4 1.4967(15) . ?
B1 N1 1.5320(14) . ?
B1 C20 1.6107(16) . ?
B1 N3 1.6393(15) . ?
N1 C13 1.3727(13) . ?
N1 N2 1.3828(13) . ?
N2 C1 1.3024(13) . ?
N3 C3 1.3442(14) . ?
N3 C2 1.3592(13) . ?
N4 C19 1.3707(13) . ?
N4 C26 1.4619(15) . ?
C1 C2 1.4792(14) . ?
C1 C7 1.4808(14) . ?
C2 C6 1.3939(15) . ?
C3 C4 1.3847(16) . ?
C3 H3 0.969(13) . ?
C4 C5 1.3849(16) . ?
C4 H4 0.966(16) . ?
C5 C6 1.3872(15) . ?
C5 H5 0.967(15) . ?
C6 H6 0.989(15) . ?
C7 C8 1.3980(14) . ?
C7 C12 1.3988(14) . ?
C8 C9 1.3916(16) . ?
C8 H8 0.969(16) . ?
C9 C10 1.3870(17) . ?
C9 H9 0.989(16) . ?
C10 C11 1.3926(16) . ?
C10 H10 0.995(15) . ?
C11 C12 1.3900(15) . ?
C11 H11 0.983(15) . ?
C12 H12 0.998(13) . ?
C13 O1 1.2328(12) . ?
C13 C14 1.4765(15) . ?
C14 C15 1.3951(14) . ?
C14 C19 1.4165(14) . ?
C15 C16 1.3828(16) . ?
C15 H15 0.981(14) . ?
C16 C17 1.3939(17) . ?
C16 H16 0.980(15) . ?
C17 C18 1.3822(15) . ?
C17 H17 0.986(14) . ?
C18 C19 1.4134(15) . ?
C18 H18 0.969(14) . ?
C20 C21 1.3929(14) . ?
C20 C25 1.4047(15) . ?
C21 C22 1.3952(16) . ?
C21 H21 1.003(16) . ?
C22 C23 1.3813(18) . ?
C22 H22 0.994(16) . ?
C23 C24 1.3904(18) . ?
C23 H23 0.992(16) . ?
C24 C25 1.3886(17) . ?
C24 H24 0.966(17) . ?
C25 H25 1.020(15) . ?
C26 H26A 0.978(16) . ?
C26 H26B 0.965(15) . ?
C26 H26C 1.008(16) . ?

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
N4 B1 N1 111.04(8) . . ?
N4 B1 C20 112.49(9) . . ?
N1 B1 C20 111.44(8) . . ?
N4 B1 N3 111.46(8) . . ?
N1 B1 N3 99.67(8) . . ?
C20 B1 N3 110.07(7) . . ?
C13 N1 N2 116.05(8) . . ?
C13 N1 B1 126.28(8) . . ?
N2 N1 B1 117.16(7) . . ?
C1 N2 N1 115.10(8) . . ?
C3 N3 C2 120.45(9) . . ?
C3 N3 B1 123.36(8) . . ?
C2 N3 B1 115.86(7) . . ?
C19 N4 C26 117.12(9) . . ?
C19 N4 B1 122.30(8) . . ?
C26 N4 B1 120.53(8) . . ?
N2 C1 C2 122.40(9) . . ?
N2 C1 C7 117.34(8) . . ?
C2 C1 C7 119.31(8) . . ?
N3 C2 C6 119.84(9) . . ?
N3 C2 C1 117.67(8) . . ?
C6 C2 C1 121.81(9) . . ?
N3 C3 C4 121.49(10) . . ?
N3 C3 H3 117.4(8) . . ?
C4 C3 H3 121.1(8) . . ?
C3 C4 C5 119.15(9) . . ?
C3 C4 H4 118.9(9) . . ?
C5 C4 H4 121.9(9) . . ?
C4 C5 C6 119.12(10) . . ?
C4 C5 H5 121.0(9) . . ?
C6 C5 H5 119.8(9) . . ?
C5 C6 C2 119.92(10) . . ?
C5 C6 H6 120.3(9) . . ?
C2 C6 H6 119.7(9) . . ?
C8 C7 C12 119.06(9) . . ?
C8 C7 C1 121.32(9) . . ?
C12 C7 C1 119.61(8) . . ?
C9 C8 C7 120.29(10) . . ?
C9 C8 H8 119.8(9) . . ?
C7 C8 H8 119.9(9) . . ?
C10 C9 C8 120.17(10) . . ?
C10 C9 H9 119.5(9) . . ?
C8 C9 H9 120.3(10) . . ?
C9 C10 C11 120.07(10) . . ?
C9 C10 H10 121.2(9) . . ?
C11 C10 H10 118.7(9) . . ?
C12 C11 C10 119.85(10) . . ?
C12 C11 H11 121.1(8) . . ?
C10 C11 H11 119.0(8) . . ?
C11 C12 C7 120.53(9) . . ?
C11 C12 H12 119.9(8) . . ?
C7 C12 H12 119.6(8) . . ?
O1 C13 N1 123.73(9) . . ?
O1 C13 C14 122.73(8) . . ?
N1 C13 C14 113.34(8) . . ?
C15 C14 C19 120.15(9) . . ?
C15 C14 C13 117.43(9) . . ?
C19 C14 C13 122.37(8) . . ?
C16 C15 C14 121.26(10) . . ?
C16 C15 H15 119.7(8) . . ?
C14 C15 H15 119.1(8) . . ?
C15 C16 C17 118.81(9) . . ?
C15 C16 H16 119.9(9) . . ?
C17 C16 H16 121.3(9) . . ?
C18 C17 C16 121.19(10) . . ?
C18 C17 H17 118.6(8) . . ?
C16 C17 H17 120.2(8) . . ?
C17 C18 C19 120.63(10) . . ?
C17 C18 H18 120.4(8) . . ?
C19 C18 H18 118.9(8) . . ?
N4 C19 C18 121.78(9) . . ?
N4 C19 C14 120.46(9) . . ?
C18 C19 C14 117.73(8) . . ?
C21 C20 C25 116.75(10) . . ?
C21 C20 B1 124.49(9) . . ?
C25 C20 B1 118.18(8) . . ?
C20 C21 C22 121.75(10) . . ?
C20 C21 H21 120.1(9) . . ?
C22 C21 H21 118.2(9) . . ?
C23 C22 C21 120.16(10) . . ?
C23 C22 H22 118.5(9) . . ?
C21 C22 H22 121.3(9) . . ?
C22 C23 C24 119.60(11) . . ?
C22 C23 H23 122.3(9) . . ?
C24 C23 H23 118.1(9) . . ?
C25 C24 C23 119.69(11) . . ?
C25 C24 H24 120.5(10) . . ?
C23 C24 H24 119.8(10) . . ?
C24 C25 C20 122.02(10) . . ?
C24 C25 H25 119.7(8) . . ?
C20 C25 H25 118.3(8) . . ?
N4 C26 H26A 109.2(9) . . ?
N4 C26 H26B 110.5(9) . . ?
H26A C26 H26B 107.5(13) . . ?
N4 C26 H26C 111.9(9) . . ?
H26A C26 H26C 107.2(13) . . ?
H26B C26 H26C 110.3(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
N4 B1 N1 C13 -8.87(13) . . . . ?
C20 B1 N1 C13 117.38(10) . . . . ?
N3 B1 N1 C13 -126.47(9) . . . . ?
N4 B1 N1 N2 179.73(8) . . . . ?
C20 B1 N1 N2 -54.02(11) . . . . ?
N3 B1 N1 N2 62.14(9) . . . . ?
C13 N1 N2 C1 149.51(9) . . . . ?
B1 N1 N2 C1 -38.20(12) . . . . ?
N4 B1 N3 C3 13.53(12) . . . . ?
N1 B1 N3 C3 130.81(9) . . . . ?
C20 B1 N3 C3 -111.99(10) . . . . ?
N4 B1 N3 C2 -159.87(8) . . . . ?
N1 B1 N3 C2 -42.59(9) . . . . ?
C20 B1 N3 C2 74.60(10) . . . . ?
N1 B1 N4 C19 -10.47(12) . . . . ?
C20 B1 N4 C19 -136.14(9) . . . . ?
N3 B1 N4 C19 99.69(10) . . . . ?
N1 B1 N4 C26 166.81(9) . . . . ?
C20 B1 N4 C26 41.13(12) . . . . ?
N3 B1 N4 C26 -83.04(11) . . . . ?
N1 N2 C1 C2 -11.64(13) . . . . ?
N1 N2 C1 C7 179.56(8) . . . . ?
C3 N3 C2 C6 1.64(13) . . . . ?
B1 N3 C2 C6 175.25(8) . . . . ?
C3 N3 C2 C1 -169.08(8) . . . . ?
B1 N3 C2 C1 4.53(11) . . . . ?
N2 C1 C2 N3 28.31(13) . . . . ?
C7 C1 C2 N3 -163.10(8) . . . . ?
N2 C1 C2 C6 -142.21(10) . . . . ?
C7 C1 C2 C6 26.37(13) . . . . ?
C2 N3 C3 C4 -1.48(14) . . . . ?
B1 N3 C3 C4 -174.59(9) . . . . ?
N3 C3 C4 C5 -0.13(16) . . . . ?
C3 C4 C5 C6 1.53(16) . . . . ?
C4 C5 C6 C2 -1.36(15) . . . . ?
N3 C2 C6 C5 -0.22(14) . . . . ?
C1 C2 C6 C5 170.10(9) . . . . ?
N2 C1 C7 C8 -152.76(9) . . . . ?
C2 C1 C7 C8 38.08(13) . . . . ?
N2 C1 C7 C12 27.97(13) . . . . ?
C2 C1 C7 C12 -141.18(9) . . . . ?
C12 C7 C8 C9 1.82(15) . . . . ?
C1 C7 C8 C9 -177.45(9) . . . . ?
C7 C8 C9 C10 -0.68(16) . . . . ?
C8 C9 C10 C11 -1.21(16) . . . . ?
C9 C10 C11 C12 1.93(16) . . . . ?
C10 C11 C12 C7 -0.77(15) . . . . ?
C8 C7 C12 C11 -1.09(14) . . . . ?
C1 C7 C12 C11 178.18(9) . . . . ?
N2 N1 C13 O1 7.77(13) . . . . ?
B1 N1 C13 O1 -163.71(9) . . . . ?
N2 N1 C13 C14 -167.18(8) . . . . ?
B1 N1 C13 C14 21.33(13) . . . . ?
O1 C13 C14 C15 -14.40(13) . . . . ?
N1 C13 C14 C15 160.61(8) . . . . ?
O1 C13 C14 C19 168.32(9) . . . . ?
N1 C13 C14 C19 -16.67(12) . . . . ?
C19 C14 C15 C16 -0.51(14) . . . . ?
C13 C14 C15 C16 -177.85(9) . . . . ?
C14 C15 C16 C17 -3.09(15) . . . . ?
C15 C16 C17 C18 2.65(16) . . . . ?
C16 C17 C18 C19 1.41(15) . . . . ?
C26 N4 C19 C18 15.17(13) . . . . ?
B1 N4 C19 C18 -167.47(9) . . . . ?
C26 N4 C19 C14 -162.56(9) . . . . ?
B1 N4 C19 C14 14.80(13) . . . . ?
C17 C18 C19 N4 177.31(9) . . . . ?
C17 C18 C19 C14 -4.90(14) . . . . ?
C15 C14 C19 N4 -177.73(9) . . . . ?
C13 C14 C19 N4 -0.52(13) . . . . ?
C15 C14 C19 C18 4.45(13) . . . . ?
C13 C14 C19 C18 -178.34(8) . . . . ?
N4 B1 C20 C21 -90.05(11) . . . . ?
N1 B1 C20 C21 144.50(9) . . . . ?
N3 B1 C20 C21 34.89(12) . . . . ?
N4 B1 C20 C25 80.98(11) . . . . ?
N1 B1 C20 C25 -44.48(12) . . . . ?
N3 B1 C20 C25 -154.09(9) . . . . ?
C25 C20 C21 C22 -1.88(15) . . . . ?
B1 C20 C21 C22 169.26(10) . . . . ?
C20 C21 C22 C23 1.00(18) . . . . ?
C21 C22 C23 C24 0.49(18) . . . . ?
C22 C23 C24 C25 -0.99(18) . . . . ?
C23 C24 C25 C20 0.04(17) . . . . ?
C21 C20 C25 C24 1.37(15) . . . . ?
B1 C20 C25 C24 -170.35(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C26 H26C N2 1.008(16) 2.629(16) 3.617(2) 166.6(12) 4_575 yes

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.062

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
####################################################################### 
# 
# 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_4-Cl
_database_code_depnum_ccdc_archive 'CCDC 2376337'
loop_
_audit_author_name
_audit_author_address
'Paul D. Boyle'
;The University of Western Ontario
Canada
;
_audit_update_record             
;
2024-08-07 deposited with the CCDC.	2024-12-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H32 B Cl3 N4 O'
_chemical_formula_weight         629.79
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.673(4)
_cell_length_b                   16.008(8)
_cell_length_c                   20.119(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3115(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9389
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.23
_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.234
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9188
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Axis Apex2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            309951
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         37.073
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             15928
_reflns_number_gt                14226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000
_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
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXT
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    Mercury
_computing_publication_material  cif2tables.py
_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.3392P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 6014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_refine_ls_abs_structure_Flack   0.486(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         15928
_refine_ls_number_parameters     516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
B1 B 0.62529(13) 0.70418(7) 0.71252(6) 0.01180(18) Uani 1 1 d . . . . .
N1 N 0.75580(11) 0.71832(6) 0.75429(5) 0.01322(16) Uani 1 1 d . . . . .
N2 N 0.81908(10) 0.65701(6) 0.79053(5) 0.01387(16) Uani 1 1 d . . . . .
N3 N 0.63341(11) 0.61090(6) 0.68616(5) 0.01309(15) Uani 1 1 d . . . . .
N4 N 0.63964(10) 0.76630(6) 0.65108(5) 0.01164(14) Uani 1 1 d . . . . .
H4N H 0.567(2) 0.7654(15) 0.6243(11) 0.030(6) Uiso 1 1 d . . . . .
C1 C 0.79673(12) 0.57967(7) 0.77478(6) 0.01337(17) Uani 1 1 d . . . . .
C2 C 0.71441(12) 0.55307(7) 0.71695(6) 0.01393(17) Uani 1 1 d . . . . .
C3 C 0.55515(14) 0.58862(7) 0.63323(6) 0.0173(2) Uani 1 1 d . . . . .
H3 H 0.502(2) 0.6319(14) 0.6155(11) 0.024(5) Uiso 1 1 d . . . . .
C4 C 0.55738(16) 0.50869(8) 0.60759(7) 0.0224(2) Uani 1 1 d . . . . .
H4 H 0.505(3) 0.4961(16) 0.5703(12) 0.035(6) Uiso 1 1 d . . . . .
C5 C 0.64353(17) 0.44956(8) 0.63670(7) 0.0232(2) Uani 1 1 d . . . . .
H5 H 0.652(3) 0.3923(16) 0.6197(12) 0.032(6) Uiso 1 1 d . . . . .
C6 C 0.72169(15) 0.47197(7) 0.69154(7) 0.0193(2) Uani 1 1 d . . . . .
H6 H 0.785(3) 0.4333(15) 0.7129(12) 0.031(6) Uiso 1 1 d . . . . .
C7 C 0.86456(13) 0.51764(7) 0.81892(6) 0.01461(18) Uani 1 1 d . . . . .
C8 C 0.79514(14) 0.44634(8) 0.84131(7) 0.0182(2) Uani 1 1 d . . . . .
H8 H 0.706(3) 0.4306(15) 0.8257(12) 0.032(6) Uiso 1 1 d . . . . .
C9 C 0.85425(15) 0.39531(8) 0.88961(7) 0.0208(2) Uani 1 1 d . . . . .
H9 H 0.803(3) 0.3506(15) 0.9066(12) 0.030(6) Uiso 1 1 d . . . . .
C10 C 0.98376(15) 0.41413(8) 0.91567(7) 0.0209(2) Uani 1 1 d . . . . .
H10 H 1.023(3) 0.3799(15) 0.9482(12) 0.031(6) Uiso 1 1 d . . . . .
C11 C 1.05515(14) 0.48382(9) 0.89219(7) 0.0215(2) Uani 1 1 d . . . . .
H11 H 1.143(2) 0.4968(14) 0.9098(10) 0.021(5) Uiso 1 1 d . . . . .
C12 C 0.99605(13) 0.53535(8) 0.84415(7) 0.0183(2) Uani 1 1 d . . . . .
H12 H 1.039(2) 0.5837(13) 0.8307(11) 0.021(5) Uiso 1 1 d . . . . .
C13 C 0.79549(14) 0.79852(7) 0.77280(6) 0.01631(19) Uani 1 1 d . . . . .
O1 O 0.88320(13) 0.81357(7) 0.81442(6) 0.0274(2) Uani 1 1 d . . . . .
C14 C 0.72130(13) 0.86613(7) 0.73587(6) 0.01409(18) Uani 1 1 d . . . . .
C15 C 0.72934(14) 0.94785(8) 0.76020(6) 0.0180(2) Uani 1 1 d . . . . .
H15 H 0.780(3) 0.9555(15) 0.8019(12) 0.033(6) Uiso 1 1 d . . . . .
C16 C 0.66303(14) 1.01272(8) 0.72735(7) 0.0191(2) Uani 1 1 d . . . . .
H16 H 0.662(3) 1.0671(16) 0.7424(13) 0.038(7) Uiso 1 1 d . . . . .
C17 C 0.58866(14) 0.99674(7) 0.66925(7) 0.0190(2) Uani 1 1 d . . . . .
H17 H 0.540(2) 1.0382(14) 0.6467(11) 0.027(5) Uiso 1 1 d . . . . .
C18 C 0.58056(13) 0.91561(7) 0.64401(6) 0.01560(18) Uani 1 1 d . . . . .
H18 H 0.527(2) 0.9051(13) 0.6051(10) 0.021(5) Uiso 1 1 d . . . . .
C19 C 0.64632(12) 0.85163(6) 0.67795(6) 0.01237(17) Uani 1 1 d . . . . .
C20 C 0.48243(12) 0.72045(6) 0.75135(5) 0.01268(17) Uani 1 1 d . . . . .
C21 C 0.35838(13) 0.74055(8) 0.71896(6) 0.01618(18) Uani 1 1 d . . . . .
H21 H 0.363(2) 0.7470(14) 0.6715(10) 0.024(5) Uiso 1 1 d . . . . .
C22 C 0.23469(13) 0.74978(8) 0.75368(7) 0.0191(2) Uani 1 1 d . . . . .
H22 H 0.152(2) 0.7603(15) 0.7307(11) 0.028(5) Uiso 1 1 d . . . . .
C23 C 0.23194(14) 0.73915(8) 0.82228(7) 0.0205(2) Uani 1 1 d . . . . .
H23 H 0.144(2) 0.7425(15) 0.8467(11) 0.028(5) Uiso 1 1 d . . . . .
C24 C 0.35355(15) 0.72053(8) 0.85581(6) 0.0201(2) Uani 1 1 d . . . . .
H24 H 0.351(2) 0.7140(14) 0.9035(11) 0.023(5) Uiso 1 1 d . . . . .
C25 C 0.47729(14) 0.71174(7) 0.82086(6) 0.01626(19) Uani 1 1 d . . . . .
H25 H 0.556(2) 0.6977(13) 0.8459(10) 0.022(5) Uiso 1 1 d . . . . .
C26 C 0.76007(13) 0.75111(8) 0.60531(6) 0.01649(19) Uani 1 1 d . . . . .
H26A H 0.754(2) 0.6983(14) 0.5854(11) 0.026(5) Uiso 1 1 d . . . . .
H26B H 0.848(2) 0.7522(14) 0.6286(11) 0.024(5) Uiso 1 1 d . . . . .
H26C H 0.764(2) 0.7917(15) 0.5724(11) 0.029(6) Uiso 1 1 d . . . . .
Cl1 Cl 0.42496(3) 0.75847(2) 0.54001(2) 0.01673(5) Uani 1 1 d . . . . .
C1M C 1.12975(17) 0.63615(10) 0.57828(8) 0.0261(3) Uani 1 1 d . . . . .
H1MA H 1.070(3) 0.6585(19) 0.5470(14) 0.053(8) Uiso 1 1 d . . . . .
H1MB H 1.202(3) 0.6721(16) 0.5925(12) 0.035(6) Uiso 1 1 d . . . . .
Cl1M Cl 1.04089(4) 0.60050(3) 0.64954(2) 0.03048(8) Uani 1 1 d . . . . .
Cl2M Cl 1.21354(5) 0.55362(3) 0.53629(2) 0.03579(9) Uani 1 1 d . . . . .
C1T C 0.86407(18) 0.26964(11) 0.48806(8) 0.0279(3) Uani 1 1 d . . . . .
C2T C 0.95435(17) 0.30122(12) 0.53558(8) 0.0304(3) Uani 1 1 d . . . . .
H2T H 1.014(3) 0.2589(17) 0.5573(13) 0.039(6) Uiso 1 1 d . . . . .
C3T C 0.96003(19) 0.38556(13) 0.54972(9) 0.0331(3) Uani 1 1 d . . . . .
H3T H 1.021(3) 0.4058(19) 0.5826(14) 0.051(8) Uiso 1 1 d . . . . .
C4T C 0.8745(2) 0.44072(12) 0.51606(9) 0.0340(3) Uani 1 1 d . . . . .
H4T H 0.882(3) 0.5018(19) 0.5219(13) 0.045(7) Uiso 1 1 d . . . . .
C5T C 0.78238(19) 0.41029(12) 0.46931(8) 0.0313(3) Uani 1 1 d . . . . .
H5T H 0.717(3) 0.4479(15) 0.4489(12) 0.032(6) Uiso 1 1 d . . . . .
C6T C 0.77731(17) 0.32559(12) 0.45512(8) 0.0286(3) Uani 1 1 d . . . . .
H6T H 0.713(3) 0.3013(17) 0.4209(14) 0.044(7) Uiso 1 1 d . . . . .
C7T C 0.8599(3) 0.17797(14) 0.47239(14) 0.0476(5) Uani 1 1 d . . . . .
H7TA H 0.853(5) 0.165(3) 0.428(2) 0.101(14) Uiso 1 1 d . . . . .
H7TB H 0.793(4) 0.148(3) 0.501(2) 0.085(12) Uiso 1 1 d . . . . .
H7TC H 0.942(4) 0.151(2) 0.4838(18) 0.080(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N1 1.5334(17) . ?
B1 N3 1.5866(16) . ?
B1 N4 1.5925(16) . ?
B1 C20 1.6086(18) . ?
N1 N2 1.3674(14) . ?
N1 C13 1.3908(16) . ?
N2 C1 1.2961(16) . ?
N3 C3 1.3543(16) . ?
N3 C2 1.3618(15) . ?
N4 C19 1.4704(15) . ?
N4 C26 1.5047(16) . ?
N4 H4N 0.88(2) . ?
C1 C2 1.4728(17) . ?
C1 C7 1.4849(16) . ?
C2 C6 1.3969(17) . ?
C3 C4 1.3797(18) . ?
C3 H3 0.93(2) . ?
C4 C5 1.391(2) . ?
C4 H4 0.93(2) . ?
C5 C6 1.385(2) . ?
C5 H5 0.98(3) . ?
C6 H6 0.97(2) . ?
C7 C12 1.3985(18) . ?
C7 C8 1.3986(18) . ?
C8 C9 1.3923(18) . ?
C8 H8 0.95(3) . ?
C9 C10 1.391(2) . ?
C9 H9 0.94(2) . ?
C10 C11 1.394(2) . ?
C10 H10 0.93(2) . ?
C11 C12 1.3934(18) . ?
C11 H11 0.94(2) . ?
C12 H12 0.92(2) . ?
C13 O1 1.2162(16) . ?
C13 C14 1.4960(17) . ?
C14 C19 1.3920(17) . ?
C14 C15 1.3990(17) . ?
C15 C16 1.3880(19) . ?
C15 H15 0.98(3) . ?
C16 C17 1.396(2) . ?
C16 H16 0.92(3) . ?
C17 C18 1.3966(18) . ?
C17 H17 0.93(2) . ?
C18 C19 1.3857(16) . ?
C18 H18 0.96(2) . ?
C20 C21 1.4028(17) . ?
C20 C25 1.4064(17) . ?
C21 C22 1.3934(18) . ?
C21 H21 0.96(2) . ?
C22 C23 1.391(2) . ?
C22 H22 0.94(2) . ?
C23 C24 1.388(2) . ?
C23 H23 0.98(2) . ?
C24 C25 1.3953(19) . ?
C24 H24 0.96(2) . ?
C25 H25 0.94(2) . ?
C26 H26A 0.94(2) . ?
C26 H26B 0.97(2) . ?
C26 H26C 0.93(2) . ?
C1M Cl2M 1.7652(18) . ?
C1M Cl1M 1.7663(17) . ?
C1M H1MA 0.93(3) . ?
C1M H1MB 0.95(3) . ?
C1T C2T 1.390(3) . ?
C1T C6T 1.395(2) . ?
C1T C7T 1.501(3) . ?
C2T C3T 1.381(3) . ?
C2T H2T 0.99(3) . ?
C3T C4T 1.386(3) . ?
C3T H3T 0.94(3) . ?
C4T C5T 1.384(3) . ?
C4T H4T 0.99(3) . ?
C5T C6T 1.387(3) . ?
C5T H5T 0.96(2) . ?
C6T H6T 1.01(3) . ?
C7T H7TA 0.92(5) . ?
C7T H7TB 0.99(4) . ?
C7T H7TC 0.93(4) . ?

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
N1 B1 N3 106.35(9) . . ?
N1 B1 N4 105.15(9) . . ?
N3 B1 N4 108.90(9) . . ?
N1 B1 C20 114.66(10) . . ?
N3 B1 C20 110.94(9) . . ?
N4 B1 C20 110.53(9) . . ?
N2 N1 C13 113.34(10) . . ?
N2 N1 B1 123.69(9) . . ?
C13 N1 B1 120.69(9) . . ?
C1 N2 N1 118.73(10) . . ?
C3 N3 C2 120.02(10) . . ?
C3 N3 B1 118.88(9) . . ?
C2 N3 B1 121.08(10) . . ?
C19 N4 C26 109.95(9) . . ?
C19 N4 B1 107.37(9) . . ?
C26 N4 B1 116.20(9) . . ?
C19 N4 H4N 105.9(15) . . ?
C26 N4 H4N 103.7(15) . . ?
B1 N4 H4N 113.2(15) . . ?
N2 C1 C2 124.02(10) . . ?
N2 C1 C7 114.76(11) . . ?
C2 C1 C7 121.20(10) . . ?
N3 C2 C6 119.62(11) . . ?
N3 C2 C1 118.29(10) . . ?
C6 C2 C1 122.04(11) . . ?
N3 C3 C4 121.96(11) . . ?
N3 C3 H3 114.3(14) . . ?
C4 C3 H3 123.7(14) . . ?
C3 C4 C5 118.90(12) . . ?
C3 C4 H4 119.7(16) . . ?
C5 C4 H4 121.4(16) . . ?
C6 C5 C4 119.10(12) . . ?
C6 C5 H5 118.4(14) . . ?
C4 C5 H5 122.5(14) . . ?
C5 C6 C2 120.32(12) . . ?
C5 C6 H6 122.1(14) . . ?
C2 C6 H6 117.6(14) . . ?
C12 C7 C8 119.02(11) . . ?
C12 C7 C1 118.90(11) . . ?
C8 C7 C1 121.75(11) . . ?
C9 C8 C7 120.43(12) . . ?
C9 C8 H8 116.6(15) . . ?
C7 C8 H8 123.0(15) . . ?
C10 C9 C8 120.39(12) . . ?
C10 C9 H9 120.5(15) . . ?
C8 C9 H9 118.9(15) . . ?
C9 C10 C11 119.44(12) . . ?
C9 C10 H10 120.2(15) . . ?
C11 C10 H10 120.3(15) . . ?
C12 C11 C10 120.36(13) . . ?
C12 C11 H11 120.0(13) . . ?
C10 C11 H11 119.7(13) . . ?
C11 C12 C7 120.33(12) . . ?
C11 C12 H12 121.2(14) . . ?
C7 C12 H12 118.3(14) . . ?
O1 C13 N1 124.04(11) . . ?
O1 C13 C14 122.23(11) . . ?
N1 C13 C14 113.73(10) . . ?
C19 C14 C15 118.54(11) . . ?
C19 C14 C13 123.02(10) . . ?
C15 C14 C13 118.43(11) . . ?
C16 C15 C14 120.49(12) . . ?
C16 C15 H15 123.1(15) . . ?
C14 C15 H15 116.3(14) . . ?
C15 C16 C17 119.98(11) . . ?
C15 C16 H16 123.7(17) . . ?
C17 C16 H16 116.3(17) . . ?
C16 C17 C18 120.24(11) . . ?
C16 C17 H17 122.5(14) . . ?
C18 C17 H17 117.2(14) . . ?
C19 C18 C17 118.84(12) . . ?
C19 C18 H18 121.6(13) . . ?
C17 C18 H18 119.5(13) . . ?
C18 C19 C14 121.90(10) . . ?
C18 C19 N4 119.03(10) . . ?
C14 C19 N4 119.05(10) . . ?
C21 C20 C25 117.03(11) . . ?
C21 C20 B1 123.12(10) . . ?
C25 C20 B1 119.82(10) . . ?
C22 C21 C20 121.73(11) . . ?
C22 C21 H21 121.9(14) . . ?
C20 C21 H21 116.4(14) . . ?
C23 C22 C21 120.07(12) . . ?
C23 C22 H22 119.8(14) . . ?
C21 C22 H22 120.1(14) . . ?
C24 C23 C22 119.49(12) . . ?
C24 C23 H23 120.0(13) . . ?
C22 C23 H23 120.4(13) . . ?
C23 C24 C25 120.23(12) . . ?
C23 C24 H24 119.0(14) . . ?
C25 C24 H24 120.7(14) . . ?
C24 C25 C20 121.43(12) . . ?
C24 C25 H25 116.6(13) . . ?
C20 C25 H25 122.0(13) . . ?
N4 C26 H26A 110.9(14) . . ?
N4 C26 H26B 112.2(13) . . ?
H26A C26 H26B 106.4(19) . . ?
N4 C26 H26C 110.8(15) . . ?
H26A C26 H26C 109.2(19) . . ?
H26B C26 H26C 107(2) . . ?
Cl2M C1M Cl1M 111.72(9) . . ?
Cl2M C1M H1MA 104.5(19) . . ?
Cl1M C1M H1MA 111.9(19) . . ?
Cl2M C1M H1MB 105.0(16) . . ?
Cl1M C1M H1MB 108.0(15) . . ?
H1MA C1M H1MB 116(2) . . ?
C2T C1T C6T 118.12(16) . . ?
C2T C1T C7T 121.11(18) . . ?
C6T C1T C7T 120.78(19) . . ?
C3T C2T C1T 121.48(15) . . ?
C3T C2T H2T 123.7(16) . . ?
C1T C2T H2T 114.8(16) . . ?
C2T C3T C4T 119.88(16) . . ?
C2T C3T H3T 120.4(18) . . ?
C4T C3T H3T 119.7(19) . . ?
C5T C4T C3T 119.47(18) . . ?
C5T C4T H4T 118.2(16) . . ?
C3T C4T H4T 122.1(17) . . ?
C4T C5T C6T 120.44(16) . . ?
C4T C5T H5T 119.5(15) . . ?
C6T C5T H5T 120.0(15) . . ?
C5T C6T C1T 120.58(15) . . ?
C5T C6T H6T 122.7(16) . . ?
C1T C6T H6T 116.7(16) . . ?
C1T C7T H7TA 116(3) . . ?
C1T C7T H7TB 111(2) . . ?
H7TA C7T H7TB 114(4) . . ?
C1T C7T H7TC 112(2) . . ?
H7TA C7T H7TC 101(3) . . ?
H7TB C7T H7TC 101(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
N3 B1 N1 N2 -32.19(14) . . . . ?
N4 B1 N1 N2 -147.61(10) . . . . ?
C20 B1 N1 N2 90.79(13) . . . . ?
N3 B1 N1 C13 166.09(10) . . . . ?
N4 B1 N1 C13 50.67(13) . . . . ?
C20 B1 N1 C13 -70.93(13) . . . . ?
C13 N1 N2 C1 -175.63(11) . . . . ?
B1 N1 N2 C1 21.46(16) . . . . ?
N1 B1 N3 C3 -160.92(11) . . . . ?
N4 B1 N3 C3 -48.07(14) . . . . ?
C20 B1 N3 C3 73.79(13) . . . . ?
N1 B1 N3 C2 20.89(14) . . . . ?
N4 B1 N3 C2 133.74(11) . . . . ?
C20 B1 N3 C2 -104.40(12) . . . . ?
N1 B1 N4 C19 -60.55(11) . . . . ?
N3 B1 N4 C19 -174.18(9) . . . . ?
C20 B1 N4 C19 63.70(11) . . . . ?
N1 B1 N4 C26 62.98(12) . . . . ?
N3 B1 N4 C26 -50.66(12) . . . . ?
C20 B1 N4 C26 -172.77(9) . . . . ?
N1 N2 C1 C2 4.43(18) . . . . ?
N1 N2 C1 C7 -177.24(10) . . . . ?
C3 N3 C2 C6 3.30(18) . . . . ?
B1 N3 C2 C6 -178.52(11) . . . . ?
C3 N3 C2 C1 -179.34(11) . . . . ?
B1 N3 C2 C1 -1.16(16) . . . . ?
N2 C1 C2 N3 -14.29(18) . . . . ?
C7 C1 C2 N3 167.48(11) . . . . ?
N2 C1 C2 C6 163.00(13) . . . . ?
C7 C1 C2 C6 -15.23(18) . . . . ?
C2 N3 C3 C4 -2.0(2) . . . . ?
B1 N3 C3 C4 179.82(12) . . . . ?
N3 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C4 C5 C6 C2 -0.3(2) . . . . ?
N3 C2 C6 C5 -2.2(2) . . . . ?
C1 C2 C6 C5 -179.43(13) . . . . ?
N2 C1 C7 C12 -36.80(16) . . . . ?
C2 C1 C7 C12 141.59(12) . . . . ?
N2 C1 C7 C8 136.52(13) . . . . ?
C2 C1 C7 C8 -45.09(17) . . . . ?
C12 C7 C8 C9 2.09(19) . . . . ?
C1 C7 C8 C9 -171.23(12) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C8 C9 C10 C11 -1.1(2) . . . . ?
C9 C10 C11 C12 1.5(2) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C8 C7 C12 C11 -1.70(19) . . . . ?
C1 C7 C12 C11 171.81(12) . . . . ?
N2 N1 C13 O1 3.86(19) . . . . ?
B1 N1 C13 O1 167.34(13) . . . . ?
N2 N1 C13 C14 -176.97(10) . . . . ?
B1 N1 C13 C14 -13.48(16) . . . . ?
O1 C13 C14 C19 164.14(14) . . . . ?
N1 C13 C14 C19 -15.06(17) . . . . ?
O1 C13 C14 C15 -14.9(2) . . . . ?
N1 C13 C14 C15 165.87(12) . . . . ?
C19 C14 C15 C16 0.43(19) . . . . ?
C13 C14 C15 C16 179.54(12) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C17 C18 C19 C14 -0.77(19) . . . . ?
C17 C18 C19 N4 -179.19(11) . . . . ?
C15 C14 C19 C18 0.26(18) . . . . ?
C13 C14 C19 C18 -178.81(12) . . . . ?
C15 C14 C19 N4 178.67(11) . . . . ?
C13 C14 C19 N4 -0.40(18) . . . . ?
C26 N4 C19 C18 90.54(13) . . . . ?
B1 N4 C19 C18 -142.18(11) . . . . ?
C26 N4 C19 C14 -87.92(13) . . . . ?
B1 N4 C19 C14 39.35(14) . . . . ?
N1 B1 C20 C21 156.30(11) . . . . ?
N3 B1 C20 C21 -83.23(13) . . . . ?
N4 B1 C20 C21 37.68(14) . . . . ?
N1 B1 C20 C25 -26.01(14) . . . . ?
N3 B1 C20 C25 94.47(12) . . . . ?
N4 B1 C20 C25 -144.62(10) . . . . ?
C25 C20 C21 C22 -1.35(18) . . . . ?
B1 C20 C21 C22 176.41(11) . . . . ?
C20 C21 C22 C23 0.1(2) . . . . ?
C21 C22 C23 C24 0.9(2) . . . . ?
C22 C23 C24 C25 -0.6(2) . . . . ?
C23 C24 C25 C20 -0.69(19) . . . . ?
C21 C20 C25 C24 1.65(17) . . . . ?
B1 C20 C25 C24 -176.18(11) . . . . ?
C6T C1T C2T C3T -0.7(2) . . . . ?
C7T C1T C2T C3T 179.20(18) . . . . ?
C1T C2T C3T C4T -0.1(3) . . . . ?
C2T C3T C4T C5T 1.1(3) . . . . ?
C3T C4T C5T C6T -1.3(3) . . . . ?
C4T C5T C6T C1T 0.5(3) . . . . ?
C2T C1T C6T C5T 0.5(2) . . . . ?
C7T C1T C6T C5T -179.41(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4N Cl1 0.88(2) 2.19(2) 3.0532(13) 167(2) . yes
C3 H3 Cl1 0.93(2) 2.64(2) 3.5350(17) 161.2(19) . yes
C18 H18 Cl1 0.96(2) 2.86(2) 3.6016(16) 134.9(16) . yes
C26 H26C Cl1 0.93(2) 2.86(2) 3.3339(17) 112.9(17) 4_566 yes
C1M H1MA Cl1 0.93(3) 2.61(3) 3.5261(19) 171(3) 4_566 yes
C1M H1MB Cl1 0.95(3) 2.77(3) 3.547(2) 139.5(19) 1_655 yes

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.052

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Bruker Apex2'
_diffrn_measurement_device       'κ-geometry diffractometer'
_exptl_crystal_preparation       Luminescent
