# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_vpn040_a
_database_code_depnum_ccdc_archive 'CCDC 2331652'
loop_
_audit_author_name
_audit_author_address
'Brian Patrick'
;The University of British Columbia
Canada
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 B N3'
_chemical_formula_weight         393.32

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'

_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                   8.4111(6)
_cell_length_b                   15.3474(11)
_cell_length_c                   17.0335(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.326(2)
_cell_angle_gamma                90
_cell_volume                     2185.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.91

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36951
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.791
_diffrn_reflns_theta_max         27.950
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5213
_reflns_number_gt                3747
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0524P)²+1.9106P] 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         5213
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1_1 N 0.72507(17) 0.16235(9) 0.63059(8) 0.0171(3) Uani 1 1 d . . . . .
C1_1 C 0.8097(2) 0.17652(11) 0.56514(10) 0.0173(3) Uani 1 1 d . . . . .
B1_1 B 0.7302(2) 0.23720(13) 0.68431(12) 0.0173(4) Uani 1 1 d . . . . .
N2_1 N 0.87149(17) 0.25809(9) 0.57374(8) 0.0172(3) Uani 1 1 d . . . . .
C2_1 C 0.8157(2) 0.11618(12) 0.50454(11) 0.0210(4) Uani 1 1 d . . . . .
H2_1 H 0.8728 0.1282 0.4621 0.025 Uiso 1 1 calc R U . . .
N3_1 N 0.90173(17) 0.38042(10) 0.64286(9) 0.0184(3) Uani 1 1 d . . . . .
C3_1 C 0.7358(2) 0.03859(12) 0.50856(11) 0.0239(4) Uani 1 1 d . . . . .
H3_1 H 0.7386 -0.0031 0.4691 0.029 Uiso 1 1 calc R U . . .
C4_1 C 0.6486(2) 0.02326(12) 0.57429(11) 0.0229(4) Uani 1 1 d . . . . .
H4_1 H 0.5933 -0.0289 0.5774 0.027 Uiso 1 1 calc R U . . .
C5_1 C 0.6446(2) 0.08335(11) 0.63255(11) 0.0200(4) Uani 1 1 d . . . . .
H5_1 H 0.5868 0.0714 0.6748 0.024 Uiso 1 1 calc R U . . .
C7_1 C 0.8286(2) 0.29883(11) 0.64205(10) 0.0170(3) Uani 1 1 d . . . . .
C8_1 C 0.9849(2) 0.38739(12) 0.57724(11) 0.0206(4) Uani 1 1 d . . . . .
H8_1 H 1.0429 0.4360 0.5646 0.025 Uiso 1 1 calc R U . . .
C9_1 C 0.9693(2) 0.31348(12) 0.53452(11) 0.0197(4) Uani 1 1 d . . . . .
H9_1 H 1.0143 0.3015 0.4882 0.024 Uiso 1 1 calc R U . . .
C10_1 C 0.6501(2) 0.24042(11) 0.76354(10) 0.0168(3) Uani 1 1 d . . . . .
C11_1 C 0.5297(2) 0.30201(11) 0.77517(10) 0.0173(3) Uani 1 1 d . . . . .
C12_1 C 0.4635(2) 0.30442(11) 0.84655(11) 0.0192(4) Uani 1 1 d . . . . .
H12_1 H 0.3838 0.3450 0.8528 0.023 Uiso 1 1 calc R U . . .
C13_1 C 0.5119(2) 0.24858(12) 0.90894(10) 0.0192(4) Uani 1 1 d . . . . .
C14_1 C 0.6303(2) 0.18786(11) 0.89770(10) 0.0189(4) Uani 1 1 d . . . . .
H14_1 H 0.6648 0.1498 0.9385 0.023 Uiso 1 1 calc R U . . .
C15_1 C 0.6988(2) 0.18257(11) 0.82672(10) 0.0171(3) Uani 1 1 d . . . . .
C16_1 C 0.8698(2) 0.45043(11) 0.69470(10) 0.0174(3) Uani 1 1 d . . . . .
C17_1 C 0.9338(2) 0.44728(11) 0.77398(10) 0.0180(4) Uani 1 1 d . . . . .
C18_1 C 0.9036(2) 0.51730(12) 0.82252(10) 0.0191(4) Uani 1 1 d . . . . .
H18_1 H 0.9476 0.5170 0.8751 0.023 Uiso 1 1 calc R U . . .
C19_1 C 0.8092(2) 0.58781(11) 0.79416(11) 0.0185(4) Uani 1 1 d . . . . .
C20_1 C 0.7433(2) 0.58742(11) 0.71536(11) 0.0195(4) Uani 1 1 d . . . . .
H20_1 H 0.6785 0.6335 0.6963 0.023 Uiso 1 1 calc R U . . .
C21_1 C 0.7724(2) 0.51956(11) 0.66462(10) 0.0194(4) Uani 1 1 d . . . . .
C22_1 C 0.4703(2) 0.36667(12) 0.71144(11) 0.0236(4) Uani 1 1 d . . . . .
H22A_1 H 0.3618 0.3825 0.7173 0.035 Uiso 1 1 calc R U . . .
H22B_1 H 0.4750 0.3407 0.6605 0.035 Uiso 1 1 calc R U . . .
H22C_1 H 0.5364 0.4178 0.7162 0.035 Uiso 1 1 calc R U . . .
C23_1 C 0.4388(2) 0.25433(14) 0.98562(11) 0.0260(4) Uani 1 1 d . . . . .
H23A_1 H 0.5025 0.2215 1.0255 0.039 Uiso 1 1 calc R U . . .
H23B_1 H 0.3323 0.2309 0.9785 0.039 Uiso 1 1 calc R U . . .
H23C_1 H 0.4349 0.3142 1.0017 0.039 Uiso 1 1 calc R U . . .
C24_1 C 0.8272(2) 0.11502(13) 0.81955(11) 0.0236(4) Uani 1 1 d . . . . .
H24A_1 H 0.8724 0.0974 0.8713 0.035 Uiso 1 1 calc R U . . .
H24B_1 H 0.9095 0.1394 0.7915 0.035 Uiso 1 1 calc R U . . .
H24C_1 H 0.7812 0.0653 0.7913 0.035 Uiso 1 1 calc R U . . .
C25_1 C 1.0318(2) 0.37056(12) 0.80644(11) 0.0235(4) Uani 1 1 d . . . . .
H25A_1 H 1.0902 0.3862 0.8560 0.035 Uiso 1 1 calc R U . . .
H25B_1 H 1.1055 0.3541 0.7698 0.035 Uiso 1 1 calc R U . . .
H25C_1 H 0.9622 0.3225 0.8141 0.035 Uiso 1 1 calc R U . . .
C26_1 C 0.7805(2) 0.66401(12) 0.84691(11) 0.0233(4) Uani 1 1 d . . . . .
H26A_1 H 0.6680 0.6765 0.8430 0.035 Uiso 1 1 calc R U . . .
H26B_1 H 0.8368 0.7142 0.8307 0.035 Uiso 1 1 calc R U . . .
H26C_1 H 0.8184 0.6498 0.9006 0.035 Uiso 1 1 calc R U . . .
C27_1 C 0.6963(2) 0.51968(13) 0.57985(11) 0.0268(4) Uani 1 1 d . . . . .
H27A_1 H 0.6069 0.5590 0.5747 0.040 Uiso 1 1 calc R U . . .
H27B_1 H 0.6602 0.4620 0.5653 0.040 Uiso 1 1 calc R U . . .
H27C_1 H 0.7734 0.5382 0.5458 0.040 Uiso 1 1 calc R U . . .


_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
N1_1 C5_1 1.391(2) . ?
N1_1 C1_1 1.404(2) . ?
N1_1 B1_1 1.466(2) . ?
C1_1 N2_1 1.357(2) . ?
C1_1 C2_1 1.392(2) . ?
B1_1 C7_1 1.493(3) . ?
B1_1 C10_1 1.574(3) . ?
N2_1 C9_1 1.402(2) . ?
N2_1 C7_1 1.402(2) . ?
C2_1 C3_1 1.373(3) . ?
N3_1 C8_1 1.386(2) . ?
N3_1 C7_1 1.394(2) . ?
N3_1 C16_1 1.435(2) . ?
C3_1 C4_1 1.424(3) . ?
C4_1 C5_1 1.358(3) . ?
C8_1 C9_1 1.346(3) . ?
C10_1 C11_1 1.415(2) . ?
C10_1 C15_1 1.420(2) . ?
C11_1 C12_1 1.392(2) . ?
C11_1 C22_1 1.514(2) . ?
C12_1 C13_1 1.391(3) . ?
C13_1 C14_1 1.392(2) . ?
C13_1 C23_1 1.506(2) . ?
C14_1 C15_1 1.398(2) . ?
C15_1 C24_1 1.512(2) . ?
C16_1 C17_1 1.398(2) . ?
C16_1 C21_1 1.402(2) . ?
C17_1 C18_1 1.396(2) . ?
C17_1 C25_1 1.507(2) . ?
C18_1 C19_1 1.397(2) . ?
C19_1 C20_1 1.394(3) . ?
C19_1 C26_1 1.510(2) . ?
C20_1 C21_1 1.392(2) . ?
C21_1 C27_1 1.514(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
C5_1 N1_1 C1_1 116.41(14) . . ?
C5_1 N1_1 B1_1 130.47(15) . . ?
C1_1 N1_1 B1_1 113.03(14) . . ?
N2_1 C1_1 C2_1 130.49(16) . . ?
N2_1 C1_1 N1_1 106.18(14) . . ?
C2_1 C1_1 N1_1 123.26(16) . . ?
N1_1 B1_1 C7_1 100.10(15) . . ?
N1_1 B1_1 C10_1 124.99(16) . . ?
C7_1 B1_1 C10_1 134.90(16) . . ?
C1_1 N2_1 C9_1 138.19(15) . . ?
C1_1 N2_1 C7_1 111.75(14) . . ?
C9_1 N2_1 C7_1 110.05(14) . . ?
C3_1 C2_1 C1_1 118.85(17) . . ?
C8_1 N3_1 C7_1 108.80(14) . . ?
C8_1 N3_1 C16_1 125.70(14) . . ?
C7_1 N3_1 C16_1 124.51(14) . . ?
C2_1 C3_1 C4_1 118.68(17) . . ?
C5_1 C4_1 C3_1 121.23(17) . . ?
C4_1 C5_1 N1_1 121.56(17) . . ?
N3_1 C7_1 N2_1 104.79(14) . . ?
N3_1 C7_1 B1_1 146.24(16) . . ?
N2_1 C7_1 B1_1 108.93(15) . . ?
C9_1 C8_1 N3_1 110.05(16) . . ?
C8_1 C9_1 N2_1 106.30(15) . . ?
C11_1 C10_1 C15_1 117.54(15) . . ?
C11_1 C10_1 B1_1 121.44(15) . . ?
C15_1 C10_1 B1_1 121.00(15) . . ?
C12_1 C11_1 C10_1 120.06(16) . . ?
C12_1 C11_1 C22_1 118.47(15) . . ?
C10_1 C11_1 C22_1 121.47(15) . . ?
C13_1 C12_1 C11_1 122.66(16) . . ?
C12_1 C13_1 C14_1 117.44(16) . . ?
C12_1 C13_1 C23_1 120.90(16) . . ?
C14_1 C13_1 C23_1 121.67(17) . . ?
C13_1 C14_1 C15_1 121.79(16) . . ?
C14_1 C15_1 C10_1 120.49(16) . . ?
C14_1 C15_1 C24_1 118.41(15) . . ?
C10_1 C15_1 C24_1 121.09(15) . . ?
C17_1 C16_1 C21_1 121.74(16) . . ?
C17_1 C16_1 N3_1 119.36(16) . . ?
C21_1 C16_1 N3_1 118.89(15) . . ?
C18_1 C17_1 C16_1 118.01(16) . . ?
C18_1 C17_1 C25_1 120.79(16) . . ?
C16_1 C17_1 C25_1 121.20(16) . . ?
C17_1 C18_1 C19_1 121.67(16) . . ?
C20_1 C19_1 C18_1 118.69(16) . . ?
C20_1 C19_1 C26_1 120.22(16) . . ?
C18_1 C19_1 C26_1 121.08(16) . . ?
C21_1 C20_1 C19_1 121.48(17) . . ?
C20_1 C21_1 C16_1 118.35(16) . . ?
C20_1 C21_1 C27_1 120.42(16) . . ?
C16_1 C21_1 C27_1 121.21(16) . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_diazadiborinine_a
_database_code_depnum_ccdc_archive 'CCDC 2331656'
loop_
_audit_author_name
_audit_author_address
'Vignesh Pattathil'
;The University of British Columbia
Canada
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H33 B2 N3'
_chemical_formula_weight         481.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.9434(6)
_cell_length_b                   12.0020(8)
_cell_length_c                   13.5298(9)
_cell_angle_alpha                105.413(2)
_cell_angle_beta                 90.951(2)
_cell_angle_gamma                109.556(2)
_cell_volume                     1310.34(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      4.866
_cell_measurement_theta_max      55.93

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31471
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.075
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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             5543
_reflns_number_gt                3871
_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       'Bruker Instrument Service v8.5.0.27 Release'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  'shelXle (C.B. Huebschle, rev 1503)'
_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)+(0.0711P)²+0.8173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5543
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.64269(19) 0.79886(14) 0.59953(12) 0.0190(4) Uani 1 1 d . . . . .
N002 N 0.30363(18) 0.73842(14) 0.57593(12) 0.0188(4) Uani 1 1 d . . . . .
N003 N 0.26888(19) 0.68706(15) 0.40538(12) 0.0212(4) Uani 1 1 d . . . . .
C004 C 0.5605(2) 0.81137(17) 0.68993(14) 0.0196(4) Uani 1 1 d . . . . .
C005 C 0.3842(2) 0.72763(17) 0.48907(14) 0.0189(4) Uani 1 1 d . . . . .
C006 C 0.6588(2) 0.74080(17) 0.39855(14) 0.0194(4) Uani 1 1 d . . . . .
C007 C 0.2966(2) 0.67797(18) 0.29965(14) 0.0200(4) Uani 1 1 d . . . . .
C008 C 0.2864(2) 0.80219(18) 0.77547(15) 0.0205(4) Uani 1 1 d . . . . .
C009 C 0.8093(2) 0.82997(17) 0.61475(15) 0.0215(4) Uani 1 1 d . . . . .
H009 H 0.865430 0.823408 0.555720 0.026 Uiso 1 1 calc R U . . .
C00A C 0.1539(2) 0.70955(19) 0.79260(15) 0.0230(4) Uani 1 1 d . . . . .
H00A H 0.117417 0.630231 0.743527 0.028 Uiso 1 1 calc R U . . .
C00B C 0.3287(2) 0.57560(18) 0.23951(15) 0.0214(4) Uani 1 1 d . . . . .
C00C C 0.7033(2) 0.63613(18) 0.36339(15) 0.0202(4) Uani 1 1 d . . . . .
C00D C 0.7698(2) 0.61549(18) 0.27069(15) 0.0222(4) Uani 1 1 d . . . . .
H00D H 0.795379 0.542855 0.246907 0.027 Uiso 1 1 calc R U . . .
C00E C 0.1412(2) 0.70362(18) 0.54377(15) 0.0228(4) Uani 1 1 d . . . . .
H00E H 0.058763 0.701592 0.587370 0.027 Uiso 1 1 calc R U . . .
C00F C 0.8932(2) 0.86845(18) 0.70823(15) 0.0237(5) Uani 1 1 d . . . . .
H00F H 1.005758 0.888585 0.713853 0.028 Uiso 1 1 calc R U . . .
C00G C 0.6954(2) 0.82761(18) 0.34118(15) 0.0212(4) Uani 1 1 d . . . . .
C00H C 0.8142(2) 0.87928(18) 0.79923(15) 0.0238(4) Uani 1 1 d . . . . .
H00H H 0.871938 0.905812 0.865851 0.029 Uiso 1 1 calc R U . . .
C00I C 0.6541(2) 0.85036(18) 0.78704(15) 0.0229(4) Uani 1 1 d . . . . .
H00I H 0.600688 0.856482 0.847277 0.028 Uiso 1 1 calc R U . . .
C00J C 0.7998(2) 0.69836(19) 0.21208(15) 0.0239(5) Uani 1 1 d . . . . .
C00K C 0.3322(2) 0.91868(19) 0.84928(15) 0.0236(4) Uani 1 1 d . . . . .
H00K H 0.421003 0.984320 0.840170 0.028 Uiso 1 1 calc R U . . .
C00L C 0.6822(2) 0.54497(19) 0.42503(16) 0.0237(5) Uani 1 1 d . . . . .
H00B H 0.625071 0.461200 0.380305 0.036 Uiso 1 1 calc R U . . .
H00C H 0.620603 0.564226 0.482240 0.036 Uiso 1 1 calc R U . . .
H00G H 0.787230 0.550304 0.452534 0.036 Uiso 1 1 calc R U . . .
C00M C 0.3267(2) 0.76727(19) 0.15981(15) 0.0235(4) Uani 1 1 d . . . . .
H00M H 0.323019 0.831057 0.131724 0.028 Uiso 1 1 calc R U . . .
C00N C 0.1223(2) 0.67346(19) 0.44005(16) 0.0248(5) Uani 1 1 d . . . . .
H00N H 0.023870 0.647134 0.397830 0.030 Uiso 1 1 calc R U . . .
C00O C 0.3665(2) 0.57560(19) 0.14029(15) 0.0243(5) Uani 1 1 d . . . . .
H00O H 0.391178 0.508049 0.098862 0.029 Uiso 1 1 calc R U . . .
C00P C 0.7640(2) 0.80481(19) 0.24950(15) 0.0246(5) Uani 1 1 d . . . . .
H00P H 0.786798 0.863716 0.211685 0.030 Uiso 1 1 calc R U . . .
C00Q C 0.2891(2) 0.77256(18) 0.25984(15) 0.0207(4) Uani 1 1 d . . . . .
C00R C 0.2515(3) 0.9406(2) 0.93504(16) 0.0275(5) Uani 1 1 d . . . . .
H00R H 0.284437 1.020482 0.983105 0.033 Uiso 1 1 calc R U . . .
C00S C 0.6660(3) 0.94778(19) 0.38009(17) 0.0287(5) Uani 1 1 d . . . . .
H00J H 0.635774 0.972140 0.321313 0.043 Uiso 1 1 calc R U . . .
H00L H 0.763638 1.012046 0.419953 0.043 Uiso 1 1 calc R U . . .
H00Q H 0.579599 0.937128 0.424237 0.043 Uiso 1 1 calc R U . . .
C00T C 0.0739(2) 0.7298(2) 0.87918(16) 0.0266(5) Uani 1 1 d . . . . .
H00T H -0.014059 0.664439 0.889496 0.032 Uiso 1 1 calc R U . . .
C00U C 0.3695(2) 0.67157(19) 0.09937(15) 0.0246(5) Uani 1 1 d . . . . .
C00V C 0.2414(3) 0.87714(19) 0.32177(16) 0.0281(5) Uani 1 1 d . . . . .
H00S H 0.270783 0.944058 0.289121 0.042 Uiso 1 1 calc R U . . .
H00U H 0.296808 0.907779 0.392015 0.042 Uiso 1 1 calc R U . . .
H00V H 0.125732 0.847590 0.324448 0.042 Uiso 1 1 calc R U . . .
C00W C 0.3200(3) 0.46873(19) 0.28012(17) 0.0280(5) Uani 1 1 d . . . . .
H00W H 0.377797 0.420203 0.238466 0.042 Uiso 1 1 calc R U . . .
H00X H 0.208019 0.416395 0.276276 0.042 Uiso 1 1 calc R U . . .
H00Y H 0.368623 0.499962 0.352094 0.042 Uiso 1 1 calc R U . . .
C00X C 0.1231(3) 0.8459(2) 0.95034(16) 0.0284(5) Uani 1 1 d . . . . .
H00Z H 0.068709 0.860282 1.009477 0.034 Uiso 1 1 calc R U . . .
C00Y C 0.8730(3) 0.6745(2) 0.11234(16) 0.0326(5) Uani 1 1 d . . . . .
H010 H 0.819335 0.696079 0.060407 0.049 Uiso 1 1 calc R U . . .
H011 H 0.860178 0.586903 0.087762 0.049 Uiso 1 1 calc R U . . .
H012 H 0.986916 0.724883 0.124140 0.049 Uiso 1 1 calc R U . . .
C00Z C 0.4233(3) 0.6747(2) -0.00490(16) 0.0327(5) Uani 1 1 d . . . . .
H013 H 0.387316 0.590503 -0.051645 0.049 Uiso 1 1 calc R U . . .
H014 H 0.540152 0.710461 0.001876 0.049 Uiso 1 1 calc R U . . .
H015 H 0.377499 0.725144 -0.032869 0.049 Uiso 1 1 calc R U . . .
B1 B 0.5637(3) 0.75725(19) 0.49584(17) 0.0196(5) Uani 1 1 d . . . . .
B2 B 0.3844(3) 0.7824(2) 0.68029(17) 0.0199(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
N001 C009 1.406(2) . ?
N001 C004 1.437(2) . ?
N001 B1 1.441(3) . ?
N002 C005 1.388(2) . ?
N002 C00E 1.396(3) . ?
N002 B2 1.452(3) . ?
N003 C00N 1.372(3) . ?
N003 C005 1.384(2) . ?
N003 C007 1.438(2) . ?
C004 C00I 1.421(3) . ?
C004 B2 1.490(3) . ?
C005 B1 1.519(3) . ?
C006 C00C 1.409(3) . ?
C006 C00G 1.416(3) . ?
C006 B1 1.584(3) . ?
C007 C00Q 1.399(3) . ?
C007 C00B 1.402(3) . ?
C008 C00A 1.400(3) . ?
C008 C00K 1.407(3) . ?
C008 B2 1.580(3) . ?
C009 C00F 1.342(3) . ?
C00A C00T 1.392(3) . ?
C00B C00O 1.390(3) . ?
C00B C00W 1.504(3) . ?
C00C C00D 1.395(3) . ?
C00C C00L 1.510(3) . ?
C00D C00J 1.392(3) . ?
C00E C00N 1.345(3) . ?
C00F C00H 1.427(3) . ?
C00G C00P 1.395(3) . ?
C00G C00S 1.510(3) . ?
C00H C00I 1.351(3) . ?
C00J C00P 1.388(3) . ?
C00J C00Y 1.510(3) . ?
C00K C00R 1.389(3) . ?
C00M C00Q 1.390(3) . ?
C00M C00U 1.393(3) . ?
C00O C00U 1.397(3) . ?
C00Q C00V 1.507(3) . ?
C00R C00X 1.383(3) . ?
C00T C00X 1.387(3) . ?
C00U C00Z 1.504(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
C009 N001 C004 117.31(16) . . ?
C009 N001 B1 119.16(16) . . ?
C004 N001 B1 123.52(16) . . ?
C005 N002 C00E 108.39(16) . . ?
C005 N002 B2 122.82(16) . . ?
C00E N002 B2 128.77(16) . . ?
C00N N003 C005 109.22(16) . . ?
C00N N003 C007 123.68(16) . . ?
C005 N003 C007 126.47(16) . . ?
C00I C004 N001 117.07(17) . . ?
C00I C004 B2 122.39(17) . . ?
N001 C004 B2 120.53(17) . . ?
N003 C005 N002 105.90(16) . . ?
N003 C005 B1 131.67(17) . . ?
N002 C005 B1 122.43(17) . . ?
C00C C006 C00G 117.80(17) . . ?
C00C C006 B1 120.96(17) . . ?
C00G C006 B1 121.18(17) . . ?
C00Q C007 C00B 122.04(18) . . ?
C00Q C007 N003 118.19(16) . . ?
C00B C007 N003 119.77(17) . . ?
C00A C008 C00K 116.34(18) . . ?
C00A C008 B2 123.98(18) . . ?
C00K C008 B2 119.68(18) . . ?
C00F C009 N001 123.50(18) . . ?
C00T C00A C008 122.16(19) . . ?
C00O C00B C007 117.54(18) . . ?
C00O C00B C00W 121.14(18) . . ?
C007 C00B C00W 121.31(18) . . ?
C00D C00C C006 120.25(18) . . ?
C00D C00C C00L 118.55(17) . . ?
C006 C00C C00L 121.20(17) . . ?
C00J C00D C00C 121.84(18) . . ?
C00N C00E N002 107.82(17) . . ?
C009 C00F C00H 120.35(19) . . ?
C00P C00G C006 120.27(18) . . ?
C00P C00G C00S 119.14(18) . . ?
C006 C00G C00S 120.56(17) . . ?
C00I C00H C00F 117.48(18) . . ?
C00H C00I C004 124.24(19) . . ?
C00P C00J C00D 117.90(18) . . ?
C00P C00J C00Y 121.20(19) . . ?
C00D C00J C00Y 120.88(19) . . ?
C00R C00K C008 121.99(19) . . ?
C00Q C00M C00U 122.20(19) . . ?
C00E C00N N003 108.66(18) . . ?
C00B C00O C00U 122.25(18) . . ?
C00J C00P C00G 121.76(18) . . ?
C00M C00Q C007 117.77(18) . . ?
C00M C00Q C00V 120.27(18) . . ?
C007 C00Q C00V 121.96(17) . . ?
C00X C00R C00K 119.9(2) . . ?
C00X C00T C00A 119.70(19) . . ?
C00M C00U C00O 117.95(18) . . ?
C00M C00U C00Z 120.65(19) . . ?
C00O C00U C00Z 121.35(18) . . ?
C00R C00X C00T 119.88(19) . . ?
N001 B1 C005 114.43(17) . . ?
N001 B1 C006 121.60(18) . . ?
C005 B1 C006 123.95(17) . . ?
N002 B2 C004 116.22(17) . . ?
N002 B2 C008 119.87(18) . . ?
C004 B2 C008 123.86(18) . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.072



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# 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_vpn041_a
_database_code_depnum_ccdc_archive 'CCDC 2331653'
loop_
_audit_author_name
_audit_author_address
'Brian Patrick'
;The University of British Columbia
Canada
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H43 B2 N3'
_chemical_formula_weight         515.33

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'

_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                   11.6929(6)
_cell_length_b                   17.5821(9)
_cell_length_c                   14.6284(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.319(2)
_cell_angle_gamma                90
_cell_volume                     2914.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9817
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      30.65

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44958
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         30.680
_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             8946
_reflns_number_gt                5786
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0584P)²+1.0051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8946
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1_1 N 0.82547(10) 0.61997(7) 0.71625(8) 0.0142(2) Uani 1 1 d . . . . .
C1_1 C 0.82469(13) 0.64410(9) 0.89954(10) 0.0171(3) Uani 1 1 d . . . . .
H1A_1 H 0.8945 0.6768 0.9082 0.020 Uiso 1 1 calc R U . . .
B1_1 B 0.75137(14) 0.64750(10) 0.78891(11) 0.0137(3) Uani 1 1 d . . . . .
N2_1 N 0.85045(10) 0.58723(7) 0.57842(8) 0.0145(2) Uani 1 1 d . . . . .
C2_1 C 0.86530(14) 0.56186(10) 0.92879(11) 0.0223(3) Uani 1 1 d . . . . .
H2A_1 H 0.9247 0.5474 0.8960 0.027 Uiso 1 1 calc R U . . .
H2B_1 H 0.9027 0.5615 0.9958 0.027 Uiso 1 1 calc R U . . .
B2_1 B 0.65604(14) 0.66867(10) 0.57518(11) 0.0146(3) Uani 1 1 d . . . . .
H1_1 H 0.5771(15) 0.6309(10) 0.5639(12) 0.022 Uiso 1 1 d . U . . .
N3_1 N 0.63926(10) 0.73165(7) 0.65147(8) 0.0145(2) Uani 1 1 d . . . . .
C3_1 C 0.76797(15) 0.50150(9) 0.90903(11) 0.0230(3) Uani 1 1 d . . . . .
H3A_1 H 0.7239 0.5050 0.9570 0.028 Uiso 1 1 calc R U . . .
H3B_1 H 0.8043 0.4516 0.9141 0.028 Uiso 1 1 calc R U . . .
C4_1 C 0.68147(15) 0.50882(9) 0.81139(11) 0.0210(3) Uani 1 1 d . . . . .
H4A_1 H 0.6131 0.4773 0.8103 0.025 Uiso 1 1 calc R U . . .
H4B_1 H 0.7193 0.4889 0.7644 0.025 Uiso 1 1 calc R U . . .
C5_1 C 0.63889(13) 0.59025(9) 0.78293(10) 0.0158(3) Uani 1 1 d . . . . .
H5_1 H 0.5924 0.5890 0.7173 0.019 Uiso 1 1 calc R U . . .
C6_1 C 0.93592(13) 0.58676(9) 0.72995(10) 0.0178(3) Uani 1 1 d . . . . .
H6_1 H 0.9902 0.5803 0.7877 0.021 Uiso 1 1 calc R U . . .
C7_1 C 0.95138(13) 0.56531(9) 0.64496(10) 0.0179(3) Uani 1 1 d . . . . .
H7_1 H 1.0168 0.5407 0.6335 0.022 Uiso 1 1 calc R U . . .
C8_1 C 0.77518(12) 0.62201(8) 0.62318(10) 0.0131(3) Uani 1 1 d . . . . .
C9_1 C 0.69736(12) 0.72948(9) 0.74525(10) 0.0135(3) Uani 1 1 d . . . . .
C10_1 C 0.74828(15) 0.67207(9) 0.96605(11) 0.0213(3) Uani 1 1 d . . . . .
H10A_1 H 0.7900 0.6605 1.0305 0.026 Uiso 1 1 calc R U . . .
H10B_1 H 0.7413 0.7270 0.9607 0.026 Uiso 1 1 calc R U . . .
C11_1 C 0.62298(14) 0.63810(10) 0.94796(11) 0.0216(3) Uani 1 1 d . . . . .
H11A_1 H 0.6277 0.5903 0.9818 0.026 Uiso 1 1 calc R U . . .
H11B_1 H 0.5745 0.6723 0.9743 0.026 Uiso 1 1 calc R U . . .
C12_1 C 0.56058(13) 0.62361(10) 0.84378(10) 0.0188(3) Uani 1 1 d . . . . .
H12A_1 H 0.5277 0.6713 0.8158 0.023 Uiso 1 1 calc R U . . .
H12B_1 H 0.4952 0.5891 0.8414 0.023 Uiso 1 1 calc R U . . .
C13_1 C 0.82583(13) 0.57027(8) 0.47887(10) 0.0142(3) Uani 1 1 d . . . . .
C14_1 C 0.88894(12) 0.60775(8) 0.42271(10) 0.0152(3) Uani 1 1 d . . . . .
C15_1 C 0.85544(13) 0.59434(9) 0.32580(10) 0.0172(3) Uani 1 1 d . . . . .
H15_1 H 0.8944 0.6201 0.2868 0.021 Uiso 1 1 calc R U . . .
C16_1 C 0.76548(13) 0.54365(9) 0.28540(10) 0.0185(3) Uani 1 1 d . . . . .
C17_1 C 0.71021(13) 0.50418(9) 0.34492(10) 0.0174(3) Uani 1 1 d . . . . .
H17_1 H 0.6522 0.4687 0.3191 0.021 Uiso 1 1 calc R U . . .
C18_1 C 0.73912(13) 0.51623(9) 0.44194(10) 0.0155(3) Uani 1 1 d . . . . .
C19_1 C 0.66885(12) 0.71173(9) 0.47967(10) 0.0140(3) Uani 1 1 d . . . . .
C20_1 C 0.59411(12) 0.69316(9) 0.39064(10) 0.0151(3) Uani 1 1 d . . . . .
C21_1 C 0.61379(13) 0.72489(9) 0.30789(10) 0.0184(3) Uani 1 1 d . . . . .
H21_1 H 0.5645 0.7111 0.2501 0.022 Uiso 1 1 calc R U . . .
C22_1 C 0.70437(14) 0.77610(9) 0.30969(11) 0.0197(3) Uani 1 1 d . . . . .
C23_1 C 0.77361(13) 0.79784(9) 0.39769(11) 0.0191(3) Uani 1 1 d . . . . .
H23_1 H 0.8323 0.8341 0.4007 0.023 Uiso 1 1 calc R U . . .
C24_1 C 0.75747(13) 0.76673(9) 0.48144(10) 0.0151(3) Uani 1 1 d . . . . .
C25_1 C 0.56986(13) 0.79142(9) 0.61530(11) 0.0188(3) Uani 1 1 d . . . . .
H25_1 H 0.5277 0.7896 0.5525 0.023 Uiso 1 1 calc R U . . .
C26_1 C 0.55921(14) 0.85447(9) 0.66743(11) 0.0206(3) Uani 1 1 d . . . . .
H26_1 H 0.5075 0.8935 0.6418 0.025 Uiso 1 1 calc R U . . .
C27_1 C 0.62772(14) 0.85865(9) 0.75953(11) 0.0201(3) Uani 1 1 d . . . . .
H27_1 H 0.6284 0.9025 0.7953 0.024 Uiso 1 1 calc R U . . .
C28_1 C 0.69475(13) 0.79629(9) 0.79677(10) 0.0164(3) Uani 1 1 d . . . . .
H28_1 H 0.7401 0.7987 0.8586 0.020 Uiso 1 1 calc R U . . .
C29_1 C 0.99144(13) 0.65984(10) 0.46346(11) 0.0208(3) Uani 1 1 d . . . . .
H29A_1 H 1.0015 0.6951 0.4159 0.031 Uiso 1 1 calc R U . . .
H29B_1 H 1.0620 0.6302 0.4846 0.031 Uiso 1 1 calc R U . . .
H29C_1 H 0.9760 0.6874 0.5158 0.031 Uiso 1 1 calc R U . . .
C30_1 C 0.73005(17) 0.53157(12) 0.18030(12) 0.0331(4) Uani 1 1 d . . . . .
H30A_1 H 0.6480 0.5437 0.1567 0.050 Uiso 1 1 calc R U . . .
H30B_1 H 0.7431 0.4794 0.1664 0.050 Uiso 1 1 calc R U . . .
H30C_1 H 0.7765 0.5639 0.1507 0.050 Uiso 1 1 calc R U . . .
C31_1 C 0.67768(14) 0.47155(10) 0.50389(11) 0.0215(3) Uani 1 1 d . . . . .
H31A_1 H 0.6276 0.4339 0.4667 0.032 Uiso 1 1 calc R U . . .
H31B_1 H 0.6309 0.5054 0.5313 0.032 Uiso 1 1 calc R U . . .
H31C_1 H 0.7355 0.4470 0.5532 0.032 Uiso 1 1 calc R U . . .
C32_1 C 0.49120(13) 0.63921(9) 0.37970(11) 0.0196(3) Uani 1 1 d . . . . .
H32A_1 H 0.4456 0.6397 0.3154 0.029 Uiso 1 1 calc R U . . .
H32B_1 H 0.4424 0.6549 0.4203 0.029 Uiso 1 1 calc R U . . .
H32C_1 H 0.5201 0.5887 0.3965 0.029 Uiso 1 1 calc R U . . .
C33_1 C 0.72791(16) 0.80592(11) 0.21929(12) 0.0289(4) Uani 1 1 d . . . . .
H33A_1 H 0.6872 0.7749 0.1674 0.043 Uiso 1 1 calc R U . . .
H33B_1 H 0.8112 0.8044 0.2237 0.043 Uiso 1 1 calc R U . . .
H33C_1 H 0.7003 0.8574 0.2093 0.043 Uiso 1 1 calc R U . . .
C34_1 C 0.83859(13) 0.79460(9) 0.57311(11) 0.0188(3) Uani 1 1 d . . . . .
H34A_1 H 0.9042 0.8213 0.5597 0.028 Uiso 1 1 calc R U . . .
H34B_1 H 0.8670 0.7519 0.6132 0.028 Uiso 1 1 calc R U . . .
H34C_1 H 0.7958 0.8282 0.6043 0.028 Uiso 1 1 calc R U . . .


_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
N1_1 C8_1 1.3434(17) . ?
N1_1 C6_1 1.3860(19) . ?
N1_1 B1_1 1.603(2) . ?
C1_1 C2_1 1.549(2) . ?
C1_1 C10_1 1.554(2) . ?
C1_1 B1_1 1.634(2) . ?
B1_1 C9_1 1.638(2) . ?
B1_1 C5_1 1.641(2) . ?
N2_1 C8_1 1.3646(18) . ?
N2_1 C7_1 1.3859(18) . ?
N2_1 C13_1 1.4439(18) . ?
C2_1 C3_1 1.530(2) . ?
B2_1 N3_1 1.618(2) . ?
B2_1 C8_1 1.620(2) . ?
B2_1 C19_1 1.628(2) . ?
N3_1 C25_1 1.3529(19) . ?
N3_1 C9_1 1.3725(18) . ?
C3_1 C4_1 1.538(2) . ?
C4_1 C5_1 1.539(2) . ?
C5_1 C12_1 1.542(2) . ?
C6_1 C7_1 1.353(2) . ?
C9_1 C28_1 1.400(2) . ?
C10_1 C11_1 1.543(2) . ?
C11_1 C12_1 1.539(2) . ?
C13_1 C18_1 1.397(2) . ?
C13_1 C14_1 1.398(2) . ?
C14_1 C15_1 1.394(2) . ?
C14_1 C29_1 1.509(2) . ?
C15_1 C16_1 1.394(2) . ?
C16_1 C17_1 1.391(2) . ?
C16_1 C30_1 1.505(2) . ?
C17_1 C18_1 1.391(2) . ?
C18_1 C31_1 1.509(2) . ?
C19_1 C24_1 1.413(2) . ?
C19_1 C20_1 1.415(2) . ?
C20_1 C21_1 1.403(2) . ?
C20_1 C32_1 1.509(2) . ?
C21_1 C22_1 1.385(2) . ?
C22_1 C23_1 1.394(2) . ?
C22_1 C33_1 1.510(2) . ?
C23_1 C24_1 1.397(2) . ?
C24_1 C34_1 1.519(2) . ?
C25_1 C26_1 1.368(2) . ?
C26_1 C27_1 1.389(2) . ?
C27_1 C28_1 1.379(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_1 N1_1 C6_1 108.44(12) . . ?
C8_1 N1_1 B1_1 119.41(12) . . ?
C6_1 N1_1 B1_1 131.95(12) . . ?
C2_1 C1_1 C10_1 107.87(13) . . ?
C2_1 C1_1 B1_1 110.95(12) . . ?
C10_1 C1_1 B1_1 111.49(12) . . ?
N1_1 B1_1 C1_1 114.10(12) . . ?
N1_1 B1_1 C9_1 103.10(11) . . ?
C1_1 B1_1 C9_1 118.38(12) . . ?
N1_1 B1_1 C5_1 109.68(12) . . ?
C1_1 B1_1 C5_1 104.33(12) . . ?
C9_1 B1_1 C5_1 106.99(12) . . ?
C8_1 N2_1 C7_1 109.01(12) . . ?
C8_1 N2_1 C13_1 125.81(12) . . ?
C7_1 N2_1 C13_1 125.01(12) . . ?
C3_1 C2_1 C1_1 115.61(13) . . ?
N3_1 B2_1 C8_1 106.60(11) . . ?
N3_1 B2_1 C19_1 109.04(12) . . ?
C8_1 B2_1 C19_1 110.84(12) . . ?
C25_1 N3_1 C9_1 120.88(13) . . ?
C25_1 N3_1 B2_1 115.16(12) . . ?
C9_1 N3_1 B2_1 123.77(12) . . ?
C2_1 C3_1 C4_1 113.89(13) . . ?
C3_1 C4_1 C5_1 115.06(13) . . ?
C4_1 C5_1 C12_1 113.35(12) . . ?
C4_1 C5_1 B1_1 110.78(12) . . ?
C12_1 C5_1 B1_1 108.56(12) . . ?
C7_1 C6_1 N1_1 108.42(13) . . ?
C6_1 C7_1 N2_1 106.48(13) . . ?
N1_1 C8_1 N2_1 107.56(12) . . ?
N1_1 C8_1 B2_1 124.53(12) . . ?
N2_1 C8_1 B2_1 127.35(12) . . ?
N3_1 C9_1 C28_1 116.32(13) . . ?
N3_1 C9_1 B1_1 117.50(12) . . ?
C28_1 C9_1 B1_1 125.86(12) . . ?
C11_1 C10_1 C1_1 116.01(13) . . ?
C12_1 C11_1 C10_1 115.54(13) . . ?
C11_1 C12_1 C5_1 115.52(12) . . ?
C18_1 C13_1 C14_1 122.10(13) . . ?
C18_1 C13_1 N2_1 118.37(12) . . ?
C14_1 C13_1 N2_1 119.53(13) . . ?
C15_1 C14_1 C13_1 117.49(13) . . ?
C15_1 C14_1 C29_1 120.01(13) . . ?
C13_1 C14_1 C29_1 122.49(13) . . ?
C16_1 C15_1 C14_1 122.14(13) . . ?
C17_1 C16_1 C15_1 118.19(14) . . ?
C17_1 C16_1 C30_1 121.05(14) . . ?
C15_1 C16_1 C30_1 120.77(14) . . ?
C16_1 C17_1 C18_1 121.94(14) . . ?
C17_1 C18_1 C13_1 117.91(13) . . ?
C17_1 C18_1 C31_1 120.12(14) . . ?
C13_1 C18_1 C31_1 121.98(13) . . ?
C24_1 C19_1 C20_1 117.25(13) . . ?
C24_1 C19_1 B2_1 121.68(12) . . ?
C20_1 C19_1 B2_1 121.02(13) . . ?
C21_1 C20_1 C19_1 120.44(14) . . ?
C21_1 C20_1 C32_1 117.07(13) . . ?
C19_1 C20_1 C32_1 122.49(13) . . ?
C22_1 C21_1 C20_1 122.00(14) . . ?
C21_1 C22_1 C23_1 117.55(14) . . ?
C21_1 C22_1 C33_1 120.87(15) . . ?
C23_1 C22_1 C33_1 121.57(15) . . ?
C22_1 C23_1 C24_1 121.94(14) . . ?
C23_1 C24_1 C19_1 120.64(13) . . ?
C23_1 C24_1 C34_1 117.23(13) . . ?
C19_1 C24_1 C34_1 122.13(13) . . ?
N3_1 C25_1 C26_1 122.67(14) . . ?
C25_1 C26_1 C27_1 118.25(14) . . ?
C28_1 C27_1 C26_1 118.44(15) . . ?
C27_1 C28_1 C9_1 122.71(14) . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_vpn046_a
_database_code_depnum_ccdc_archive 'CCDC 2331654'
loop_
_audit_author_name
_audit_author_address
'Brian Patrick'
;The University of British Columbia
Canada
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 B2 F3 N3'
_chemical_formula_weight         461.13

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'
F F 0.0171 0.0103 '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                   13.4867(18)
_cell_length_b                   12.7379(17)
_cell_length_c                   13.3863(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2299.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      30.60

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43912
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         30.624
_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 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             6817
_reflns_number_gt                6226
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.916
_reflns_Friedel_fraction_full    0.967

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0514P)²+0.3594P] 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_abs_structure_details 
;
 Flack x determined using 2594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6817
_refine_ls_number_parameters     313
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1_1 F 0.73271(7) 0.62754(7) 0.43296(8) 0.01366(19) Uani 1 1 d . . . . .
N1_1 N 0.70262(10) 0.53582(10) 0.58570(11) 0.0126(2) Uani 1 1 d . . . . .
C1_1 C 0.65575(12) 0.44116(12) 0.58240(13) 0.0136(3) Uani 1 1 d . . . . .
B1_1 B 0.67060(13) 0.63592(13) 0.51759(14) 0.0110(3) Uani 1 1 d . . . . .
F2_1 F 0.49657(8) 0.34926(8) 0.54619(9) 0.0211(2) Uani 1 1 d . . . . .
N2_1 N 0.51196(10) 0.52209(11) 0.47652(11) 0.0128(3) Uani 1 1 d . . . . .
C2_1 C 0.69013(14) 0.36073(13) 0.64486(14) 0.0184(3) Uani 1 1 d . . . . .
H2_1 H 0.6584 0.2959 0.6442 0.022 Uiso 1 1 calc R U . . .
B2_1 B 0.56595(14) 0.41777(14) 0.50441(15) 0.0142(3) Uani 1 1 d . . . . .
F3_1 F 0.60523(8) 0.37345(8) 0.41630(9) 0.0199(2) Uani 1 1 d . . . . .
N3_1 N 0.49016(9) 0.68760(10) 0.44500(11) 0.0123(2) Uani 1 1 d . . . . .
C3_1 C 0.77049(14) 0.37608(14) 0.70754(14) 0.0202(4) Uani 1 1 d . . . . .
H3_1 H 0.7919 0.3226 0.7496 0.024 Uiso 1 1 calc R U . . .
C4_1 C 0.81888(14) 0.47264(14) 0.70679(14) 0.0196(3) Uani 1 1 d . . . . .
H4_1 H 0.8739 0.4845 0.7471 0.024 Uiso 1 1 calc R U . . .
C5_1 C 0.78300(12) 0.55051(13) 0.64449(14) 0.0161(3) Uani 1 1 d . . . . .
H5_1 H 0.8152 0.6151 0.6430 0.019 Uiso 1 1 calc R U . . .
C6_1 C 0.55647(11) 0.61622(12) 0.48038(12) 0.0110(3) Uani 1 1 d . . . . .
C8_1 C 0.40308(12) 0.63668(13) 0.41950(14) 0.0160(3) Uani 1 1 d . . . . .
H8_1 H 0.3460 0.6676 0.3938 0.019 Uiso 1 1 calc R U . . .
C9_1 C 0.41671(12) 0.53306(13) 0.43908(14) 0.0159(3) Uani 1 1 d . . . . .
H9_1 H 0.3708 0.4796 0.4292 0.019 Uiso 1 1 calc R U . . .
C10_1 C 0.68082(11) 0.74377(12) 0.58124(13) 0.0108(3) Uani 1 1 d . . . . .
C11_1 C 0.62688(11) 0.75701(12) 0.67149(13) 0.0118(3) Uani 1 1 d . . . . .
C12_1 C 0.62300(12) 0.85494(13) 0.71954(13) 0.0135(3) Uani 1 1 d . . . . .
H12_1 H 0.5857 0.8619 0.7776 0.016 Uiso 1 1 calc R U . . .
C13_1 C 0.67353(12) 0.94175(12) 0.68261(13) 0.0138(3) Uani 1 1 d . . . . .
C14_1 C 0.73124(11) 0.92743(12) 0.59713(13) 0.0137(3) Uani 1 1 d . . . . .
H14_1 H 0.7678 0.9838 0.5728 0.016 Uiso 1 1 calc R U . . .
C15_1 C 0.73608(11) 0.83143(12) 0.54668(12) 0.0118(3) Uani 1 1 d . . . . .
C16_1 C 0.50826(11) 0.79914(11) 0.43234(13) 0.0116(3) Uani 1 1 d . . . . .
C17_1 C 0.56318(11) 0.83230(13) 0.34951(13) 0.0130(3) Uani 1 1 d . . . . .
C18_1 C 0.58750(12) 0.93899(13) 0.34395(14) 0.0151(3) Uani 1 1 d . . . . .
H18_1 H 0.6240 0.9631 0.2897 0.018 Uiso 1 1 calc R U . . .
C19_1 C 0.55845(12) 1.01017(12) 0.41775(14) 0.0152(3) Uani 1 1 d . . . . .
C20_1 C 0.49870(12) 0.97426(13) 0.49556(13) 0.0148(3) Uani 1 1 d . . . . .
H20_1 H 0.4763 1.0219 0.5431 0.018 Uiso 1 1 calc R U . . .
C21_1 C 0.47152(11) 0.86883(12) 0.50412(13) 0.0132(3) Uani 1 1 d . . . . .
C22_1 C 0.57235(13) 0.66700(13) 0.72194(13) 0.0164(3) Uani 1 1 d . . . . .
H22A_1 H 0.5371 0.6270 0.6726 0.025 Uiso 1 1 calc R U . . .
H22B_1 H 0.5262 0.6946 0.7698 0.025 Uiso 1 1 calc R U . . .
H22C_1 H 0.6193 0.6225 0.7553 0.025 Uiso 1 1 calc R U . . .
C23_1 C 0.66452(14) 1.04811(14) 0.73190(15) 0.0203(4) Uani 1 1 d . . . . .
H23A_1 H 0.7234 1.0883 0.7191 0.030 Uiso 1 1 calc R U . . .
H23B_1 H 0.6565 1.0392 0.8026 0.030 Uiso 1 1 calc R U . . .
H23C_1 H 0.6080 1.0844 0.7053 0.030 Uiso 1 1 calc R U . . .
C24_1 C 0.80265(12) 0.82732(13) 0.45565(13) 0.0153(3) Uani 1 1 d . . . . .
H24A_1 H 0.7640 0.8092 0.3980 0.023 Uiso 1 1 calc R U . . .
H24B_1 H 0.8533 0.7754 0.4657 0.023 Uiso 1 1 calc R U . . .
H24C_1 H 0.8329 0.8947 0.4456 0.023 Uiso 1 1 calc R U . . .
C25_1 C 0.59566(13) 0.75720(13) 0.26890(14) 0.0172(3) Uani 1 1 d . . . . .
H25A_1 H 0.5385 0.7237 0.2404 0.026 Uiso 1 1 calc R U . . .
H25B_1 H 0.6386 0.7049 0.2972 0.026 Uiso 1 1 calc R U . . .
H25C_1 H 0.6306 0.7951 0.2178 0.026 Uiso 1 1 calc R U . . .
C26_1 C 0.59360(14) 1.12274(13) 0.41531(17) 0.0216(4) Uani 1 1 d . . . . .
H26A_1 H 0.6032 1.1442 0.3473 0.032 Uiso 1 1 calc R U . . .
H26B_1 H 0.6551 1.1285 0.4509 0.032 Uiso 1 1 calc R U . . .
H26C_1 H 0.5448 1.1670 0.4462 0.032 Uiso 1 1 calc R U . . .
C27_1 C 0.40476(12) 0.83218(13) 0.58771(15) 0.0171(3) Uani 1 1 d . . . . .
H27A_1 H 0.3379 0.8269 0.5637 0.026 Uiso 1 1 calc R U . . .
H27B_1 H 0.4074 0.8817 0.6417 0.026 Uiso 1 1 calc R U . . .
H27C_1 H 0.4266 0.7647 0.6109 0.026 Uiso 1 1 calc R U . . .


_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
F1_1 B1_1 1.413(2) . ?
N1_1 C5_1 1.353(2) . ?
N1_1 C1_1 1.3622(19) . ?
N1_1 B1_1 1.626(2) . ?
C1_1 C2_1 1.401(2) . ?
C1_1 B2_1 1.627(3) . ?
B1_1 C10_1 1.622(2) . ?
B1_1 C6_1 1.637(2) . ?
F2_1 B2_1 1.397(2) . ?
N2_1 C6_1 1.3419(19) . ?
N2_1 C9_1 1.386(2) . ?
N2_1 B2_1 1.561(2) . ?
C2_1 C3_1 1.384(3) . ?
B2_1 F3_1 1.411(2) . ?
N3_1 C6_1 1.360(2) . ?
N3_1 C8_1 1.384(2) . ?
N3_1 C16_1 1.4516(19) . ?
C3_1 C4_1 1.392(3) . ?
C4_1 C5_1 1.383(2) . ?
C8_1 C9_1 1.358(2) . ?
C10_1 C15_1 1.420(2) . ?
C10_1 C11_1 1.420(2) . ?
C11_1 C12_1 1.405(2) . ?
C11_1 C22_1 1.520(2) . ?
C12_1 C13_1 1.390(2) . ?
C13_1 C14_1 1.396(2) . ?
C13_1 C23_1 1.512(2) . ?
C14_1 C15_1 1.398(2) . ?
C15_1 C24_1 1.514(2) . ?
C16_1 C17_1 1.399(2) . ?
C16_1 C21_1 1.399(2) . ?
C17_1 C18_1 1.400(2) . ?
C17_1 C25_1 1.507(2) . ?
C18_1 C19_1 1.397(2) . ?
C19_1 C20_1 1.394(2) . ?
C19_1 C26_1 1.511(2) . ?
C20_1 C21_1 1.397(2) . ?
C21_1 C27_1 1.510(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
C5_1 N1_1 C1_1 120.89(15) . . ?
C5_1 N1_1 B1_1 115.51(13) . . ?
C1_1 N1_1 B1_1 123.55(13) . . ?
N1_1 C1_1 C2_1 118.31(15) . . ?
N1_1 C1_1 B2_1 121.90(14) . . ?
C2_1 C1_1 B2_1 119.70(14) . . ?
F1_1 B1_1 C10_1 115.76(13) . . ?
F1_1 B1_1 N1_1 103.47(12) . . ?
C10_1 B1_1 N1_1 110.30(13) . . ?
F1_1 B1_1 C6_1 107.56(13) . . ?
C10_1 B1_1 C6_1 111.68(12) . . ?
N1_1 B1_1 C6_1 107.47(12) . . ?
C6_1 N2_1 C9_1 109.78(13) . . ?
C6_1 N2_1 B2_1 122.88(13) . . ?
C9_1 N2_1 B2_1 127.22(13) . . ?
C3_1 C2_1 C1_1 121.16(16) . . ?
F2_1 B2_1 F3_1 109.66(14) . . ?
F2_1 B2_1 N2_1 108.37(14) . . ?
F3_1 B2_1 N2_1 108.42(14) . . ?
F2_1 B2_1 C1_1 110.87(14) . . ?
F3_1 B2_1 C1_1 109.29(14) . . ?
N2_1 B2_1 C1_1 110.19(13) . . ?
C6_1 N3_1 C8_1 109.30(13) . . ?
C6_1 N3_1 C16_1 125.75(13) . . ?
C8_1 N3_1 C16_1 124.92(13) . . ?
C2_1 C3_1 C4_1 119.16(16) . . ?
C5_1 C4_1 C3_1 118.28(17) . . ?
N1_1 C5_1 C4_1 122.13(16) . . ?
N2_1 C6_1 N3_1 106.84(13) . . ?
N2_1 C6_1 B1_1 124.70(13) . . ?
N3_1 C6_1 B1_1 128.43(13) . . ?
C9_1 C8_1 N3_1 107.03(14) . . ?
C8_1 C9_1 N2_1 107.06(14) . . ?
C15_1 C10_1 C11_1 116.91(14) . . ?
C15_1 C10_1 B1_1 122.64(14) . . ?
C11_1 C10_1 B1_1 120.24(13) . . ?
C12_1 C11_1 C10_1 120.93(14) . . ?
C12_1 C11_1 C22_1 116.64(15) . . ?
C10_1 C11_1 C22_1 122.42(14) . . ?
C13_1 C12_1 C11_1 121.70(15) . . ?
C12_1 C13_1 C14_1 117.45(14) . . ?
C12_1 C13_1 C23_1 121.22(15) . . ?
C14_1 C13_1 C23_1 121.31(15) . . ?
C13_1 C14_1 C15_1 122.43(14) . . ?
C14_1 C15_1 C10_1 120.38(14) . . ?
C14_1 C15_1 C24_1 116.52(14) . . ?
C10_1 C15_1 C24_1 123.10(14) . . ?
C17_1 C16_1 C21_1 122.71(14) . . ?
C17_1 C16_1 N3_1 118.51(14) . . ?
C21_1 C16_1 N3_1 118.77(14) . . ?
C16_1 C17_1 C18_1 117.35(15) . . ?
C16_1 C17_1 C25_1 121.98(14) . . ?
C18_1 C17_1 C25_1 120.67(15) . . ?
C19_1 C18_1 C17_1 121.79(16) . . ?
C20_1 C19_1 C18_1 118.52(15) . . ?
C20_1 C19_1 C26_1 120.60(16) . . ?
C18_1 C19_1 C26_1 120.85(16) . . ?
C19_1 C20_1 C21_1 121.90(16) . . ?
C20_1 C21_1 C16_1 117.44(15) . . ?
C20_1 C21_1 C27_1 120.96(15) . . ?
C16_1 C21_1 C27_1 121.60(14) . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_vpn051
_database_code_depnum_ccdc_archive 'CCDC 2331660'
loop_
_audit_author_name
_audit_author_address
'Conor Pranckevicius'
;The University of British Columbia
Canada
;
_audit_update_record             
;
2024-02-08 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H33 B2 Cl2 N3'
_chemical_formula_weight         552.13

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'
B B 0.0013 0.0007 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.2484(7)
_cell_length_b                   8.6731(8)
_cell_length_c                   22.3744(19)
_cell_angle_alpha                81.768(2)
_cell_angle_beta                 85.754(2)
_cell_angle_gamma                62.036(2)
_cell_volume                     1399.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9489
_cell_measurement_theta_min      2.6794
_cell_measurement_theta_max      26.4439

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.260
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27539
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.679
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5714
_reflns_number_gt                3880
_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       'Bruker Instrument Service v8.5.0.27 Release'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  'shelXle (C.B. Huebschle, rev 1503)'
_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)+(0.0805P)²+3.2042P] 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         5714
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.2009
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.003
_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 0.49347(12) 0.75041(12) 0.28830(4) 0.0260(2) Uani 1 1 d . . . . .
Cl2 Cl 0.08260(12) 0.34710(12) 0.37058(4) 0.0248(2) Uani 1 1 d . . . . .
N1 N 0.4963(4) 0.4105(4) 0.22144(13) 0.0190(6) Uani 1 1 d . . . . .
N2 N 0.3621(4) 0.3917(4) 0.30698(13) 0.0193(6) Uani 1 1 d . . . . .
N3 N 0.1660(4) 0.7644(4) 0.32545(13) 0.0175(6) Uani 1 1 d . . . . .
C1 C 0.7775(6) 0.7070(5) 0.02198(18) 0.0318(9) Uani 1 1 d . . . . .
H7 H 0.8203 0.6357 -0.0116 0.048 Uiso 1 1 calc R U . . .
H8 H 0.8791 0.7205 0.0363 0.048 Uiso 1 1 calc R U . . .
H1 H 0.6774 0.8232 0.0082 0.048 Uiso 1 1 calc R U . . .
C2 C 0.7098(5) 0.6178(5) 0.07258(16) 0.0232(8) Uani 1 1 d . . . . .
B2 B 0.2538(6) 0.4378(5) 0.36727(18) 0.0198(8) Uani 1 1 d . . . . .
C3 C 0.8132(5) 0.5316(5) 0.12433(16) 0.0221(8) Uani 1 1 d . . . . .
H13 H 0.9322 0.5222 0.1262 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7474(5) 0.4586(4) 0.17357(16) 0.0199(8) Uani 1 1 d . . . . .
C5 C 0.5704(5) 0.4758(4) 0.16924(15) 0.0192(7) Uani 1 1 d . . . . .
C6 C 0.3830(5) 0.5064(4) 0.26445(15) 0.0174(7) Uani 1 1 d . . . . .
C8 C 0.3915(5) 0.3529(4) 0.42360(16) 0.0195(8) Uani 1 1 d . . . . .
C9 C 0.3591(5) 0.2617(5) 0.47607(17) 0.0256(8) Uani 1 1 d . . . . .
H3 H 0.2545 0.2423 0.4781 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4760(6) 0.1989(5) 0.52512(17) 0.0312(9) Uani 1 1 d . . . . .
H33 H 0.4505 0.1381 0.5603 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6297(5) 0.2248(5) 0.52282(17) 0.0273(9) Uani 1 1 d . . . . .
H2 H 0.7101 0.1814 0.5563 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1395(5) 0.6477(4) 0.36677(15) 0.0180(7) Uani 1 1 d . . . . .
C13 C 0.4622(5) 0.2229(5) 0.29129(16) 0.0239(8) Uani 1 1 d . . . . .
H15 H 0.4705 0.1182 0.3140 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5452(5) 0.2342(5) 0.23818(17) 0.0233(8) Uani 1 1 d . . . . .
H14 H 0.6227 0.1394 0.2162 0.028 Uiso 1 1 calc R U . . .
C15 C 0.8622(5) 0.3617(5) 0.22844(17) 0.0254(8) Uani 1 1 d . . . . .
H5 H 0.8839 0.2394 0.2337 0.038 Uiso 1 1 calc R U . . .
H6 H 0.7979 0.4180 0.2640 0.038 Uiso 1 1 calc R U . . .
H4 H 0.9800 0.3643 0.2234 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5412(5) 0.6190(5) 0.06867(16) 0.0216(8) Uani 1 1 d . . . . .
H9 H 0.4728 0.6712 0.0325 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4701(5) 0.5462(5) 0.11615(16) 0.0204(8) Uani 1 1 d . . . . .
C18 C 0.2939(5) 0.5402(5) 0.10789(18) 0.0272(9) Uani 1 1 d . . . . .
H12 H 0.1952 0.6601 0.0979 0.041 Uiso 1 1 calc R U . . .
H11 H 0.2627 0.4858 0.1454 0.041 Uiso 1 1 calc R U . . .
H10 H 0.3091 0.4708 0.0751 0.041 Uiso 1 1 calc R U . . .
C19 C 0.1749(5) 0.8352(4) 0.20756(15) 0.0176(7) Uani 1 1 d . . . . .
C20 C 0.2207(5) 0.9409(4) 0.16289(15) 0.0184(7) Uani 1 1 d . . . . .
C21 C 0.3948(5) 0.9586(5) 0.16295(17) 0.0253(8) Uani 1 1 d . . . . .
H16 H 0.5011 0.8414 0.1670 0.038 Uiso 1 1 calc R U . . .
H17 H 0.3912 1.0200 0.1969 0.038 Uiso 1 1 calc R U . . .
H18 H 0.4046 1.0258 0.1250 0.038 Uiso 1 1 calc R U . . .
C22 C 0.1037(5) 1.0376(5) 0.11437(16) 0.0225(8) Uani 1 1 d . . . . .
H19 H 0.1383 1.1079 0.0852 0.027 Uiso 1 1 calc R U . . .
C23 C -0.0604(5) 1.0356(5) 0.10680(16) 0.0224(8) Uani 1 1 d . . . . .
C24 C -0.1848(5) 1.1424(5) 0.05418(17) 0.0290(9) Uani 1 1 d . . . . .
H22 H -0.1443 1.0766 0.0192 0.043 Uiso 1 1 calc R U . . .
H21 H -0.1801 1.2540 0.0441 0.043 Uiso 1 1 calc R U . . .
H20 H -0.3110 1.1660 0.0650 0.043 Uiso 1 1 calc R U . . .
C25 C -0.1051(5) 0.9300(5) 0.14986(16) 0.0200(7) Uani 1 1 d . . . . .
H23 H -0.2151 0.9233 0.1453 0.024 Uiso 1 1 calc R U . . .
C26 C 0.0054(5) 0.8331(4) 0.19972(15) 0.0189(7) Uani 1 1 d . . . . .
C27 C -0.0676(5) 0.7289(5) 0.24264(17) 0.0237(8) Uani 1 1 d . . . . .
H24 H -0.1609 0.7161 0.2222 0.036 Uiso 1 1 calc R U . . .
H26 H -0.1225 0.7907 0.2780 0.036 Uiso 1 1 calc R U . . .
H25 H 0.0332 0.6123 0.2555 0.036 Uiso 1 1 calc R U . . .
C28 C 0.0758(5) 0.9397(5) 0.32996(16) 0.0193(7) Uani 1 1 d . . . . .
H30 H 0.1023 1.0175 0.3015 0.023 Uiso 1 1 calc R U . . .
C29 C -0.0520(5) 1.0072(5) 0.37415(16) 0.0219(8) Uani 1 1 d . . . . .
H29 H -0.1148 1.1303 0.3762 0.026 Uiso 1 1 calc R U . . .
C30 C -0.0885(5) 0.8935(5) 0.41591(17) 0.0240(8) Uani 1 1 d . . . . .
H27 H -0.1794 0.9375 0.4463 0.029 Uiso 1 1 calc R U . . .
C31 C 0.0090(5) 0.7157(5) 0.41271(17) 0.0233(8) Uani 1 1 d . . . . .
H28 H -0.0124 0.6368 0.4423 0.028 Uiso 1 1 calc R U . . .
C32 C 0.5475(5) 0.3775(5) 0.42296(17) 0.0234(8) Uani 1 1 d . . . . .
H31 H 0.5730 0.4396 0.3881 0.028 Uiso 1 1 calc R U . . .
C33 C 0.6662(5) 0.3142(5) 0.47146(17) 0.0241(8) Uani 1 1 d . . . . .
H32 H 0.7718 0.3319 0.4696 0.029 Uiso 1 1 calc R U . . .
B1 B 0.2958(5) 0.7147(5) 0.26706(18) 0.0191(8) 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 1.900(4) . ?
Cl2 B2 1.905(4) . ?
N1 C6 1.363(4) . ?
N1 C14 1.386(5) . ?
N1 C5 1.445(4) . ?
N2 C6 1.338(4) . ?
N2 C13 1.385(5) . ?
N2 B2 1.555(5) . ?
N3 C12 1.356(4) . ?
N3 C28 1.359(4) . ?
N3 B1 1.600(5) . ?
C1 C2 1.501(5) . ?
C1 H7 0.9800 . ?
C1 H8 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.388(5) . ?
C2 C16 1.395(5) . ?
B2 C8 1.607(5) . ?
B2 C12 1.609(5) . ?
C3 C4 1.394(5) . ?
C3 H13 0.9500 . ?
C4 C5 1.406(5) . ?
C4 C15 1.497(5) . ?
C5 C17 1.390(5) . ?
C6 B1 1.609(5) . ?
C8 C32 1.398(5) . ?
C8 C9 1.400(5) . ?
C9 C10 1.387(5) . ?
C9 H3 0.9500 . ?
C10 C11 1.383(6) . ?
C10 H33 0.9500 . ?
C11 C33 1.388(5) . ?
C11 H2 0.9500 . ?
C12 C31 1.406(5) . ?
C13 C14 1.341(5) . ?
C13 H15 0.9500 . ?
C14 H14 0.9500 . ?
C15 H5 0.9800 . ?
C15 H6 0.9800 . ?
C15 H4 0.9800 . ?
C16 C17 1.390(5) . ?
C16 H9 0.9500 . ?
C17 C18 1.504(5) . ?
C18 H12 0.9800 . ?
C18 H11 0.9800 . ?
C18 H10 0.9800 . ?
C19 C20 1.410(5) . ?
C19 C26 1.430(5) . ?
C19 B1 1.637(5) . ?
C20 C22 1.396(5) . ?
C20 C21 1.513(5) . ?
C21 H16 0.9800 . ?
C21 H17 0.9800 . ?
C21 H18 0.9800 . ?
C22 C23 1.384(5) . ?
C22 H19 0.9500 . ?
C23 C25 1.384(5) . ?
C23 C24 1.508(5) . ?
C24 H22 0.9800 . ?
C24 H21 0.9800 . ?
C24 H20 0.9800 . ?
C25 C26 1.395(5) . ?
C25 H23 0.9500 . ?
C26 C27 1.509(5) . ?
C27 H24 0.9800 . ?
C27 H26 0.9800 . ?
C27 H25 0.9800 . ?
C28 C29 1.365(5) . ?
C28 H30 0.9500 . ?
C29 C30 1.381(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.375(5) . ?
C30 H27 0.9500 . ?
C31 H28 0.9500 . ?
C32 C33 1.386(5) . ?
C32 H31 0.9500 . ?
C33 H32 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
C6 N1 C14 109.3(3) . . ?
C6 N1 C5 126.5(3) . . ?
C14 N1 C5 124.0(3) . . ?
C6 N2 C13 109.7(3) . . ?
C6 N2 B2 125.5(3) . . ?
C13 N2 B2 124.7(3) . . ?
C12 N3 C28 121.1(3) . . ?
C12 N3 B1 125.0(3) . . ?
C28 N3 B1 113.9(3) . . ?
C2 C1 H7 109.5 . . ?
C2 C1 H8 109.5 . . ?
H7 C1 H8 109.5 . . ?
C2 C1 H1 109.5 . . ?
H7 C1 H1 109.5 . . ?
H8 C1 H1 109.5 . . ?
C3 C2 C16 118.3(3) . . ?
C3 C2 C1 121.0(3) . . ?
C16 C2 C1 120.7(3) . . ?
N2 B2 C8 110.4(3) . . ?
N2 B2 C12 110.4(3) . . ?
C8 B2 C12 110.1(3) . . ?
N2 B2 Cl2 106.0(2) . . ?
C8 B2 Cl2 111.8(3) . . ?
C12 B2 Cl2 107.9(3) . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H13 119.0 . . ?
C4 C3 H13 119.0 . . ?
C3 C4 C5 117.5(3) . . ?
C3 C4 C15 121.4(3) . . ?
C5 C4 C15 121.1(3) . . ?
C17 C5 C4 122.1(3) . . ?
C17 C5 N1 119.9(3) . . ?
C4 C5 N1 117.9(3) . . ?
N2 C6 N1 106.5(3) . . ?
N2 C6 B1 125.2(3) . . ?
N1 C6 B1 128.3(3) . . ?
C32 C8 C9 116.8(3) . . ?
C32 C8 B2 119.7(3) . . ?
C9 C8 B2 123.3(3) . . ?
C10 C9 C8 121.6(4) . . ?
C10 C9 H3 119.2 . . ?
C8 C9 H3 119.2 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H33 120.0 . . ?
C9 C10 H33 120.0 . . ?
C10 C11 C33 119.9(4) . . ?
C10 C11 H2 120.1 . . ?
C33 C11 H2 120.1 . . ?
N3 C12 C31 117.4(3) . . ?
N3 C12 B2 123.6(3) . . ?
C31 C12 B2 118.9(3) . . ?
C14 C13 N2 107.6(3) . . ?
C14 C13 H15 126.2 . . ?
N2 C13 H15 126.2 . . ?
C13 C14 N1 107.0(3) . . ?
C13 C14 H14 126.5 . . ?
N1 C14 H14 126.5 . . ?
C4 C15 H5 109.5 . . ?
C4 C15 H6 109.5 . . ?
H5 C15 H6 109.5 . . ?
C4 C15 H4 109.5 . . ?
H5 C15 H4 109.5 . . ?
H6 C15 H4 109.5 . . ?
C17 C16 C2 122.0(3) . . ?
C17 C16 H9 119.0 . . ?
C2 C16 H9 119.0 . . ?
C5 C17 C16 117.7(3) . . ?
C5 C17 C18 122.6(3) . . ?
C16 C17 C18 119.7(3) . . ?
C17 C18 H12 109.5 . . ?
C17 C18 H11 109.5 . . ?
H12 C18 H11 109.5 . . ?
C17 C18 H10 109.5 . . ?
H12 C18 H10 109.5 . . ?
H11 C18 H10 109.5 . . ?
C20 C19 C26 116.4(3) . . ?
C20 C19 B1 126.7(3) . . ?
C26 C19 B1 116.9(3) . . ?
C22 C20 C19 120.6(3) . . ?
C22 C20 C21 115.3(3) . . ?
C19 C20 C21 124.1(3) . . ?
C20 C21 H16 109.5 . . ?
C20 C21 H17 109.5 . . ?
H16 C21 H17 109.5 . . ?
C20 C21 H18 109.5 . . ?
H16 C21 H18 109.5 . . ?
H17 C21 H18 109.5 . . ?
C23 C22 C20 123.1(3) . . ?
C23 C22 H19 118.5 . . ?
C20 C22 H19 118.5 . . ?
C25 C23 C22 116.8(3) . . ?
C25 C23 C24 121.2(3) . . ?
C22 C23 C24 122.0(3) . . ?
C23 C24 H22 109.5 . . ?
C23 C24 H21 109.5 . . ?
H22 C24 H21 109.5 . . ?
C23 C24 H20 109.5 . . ?
H22 C24 H20 109.5 . . ?
H21 C24 H20 109.5 . . ?
C23 C25 C26 122.4(3) . . ?
C23 C25 H23 118.8 . . ?
C26 C25 H23 118.8 . . ?
C25 C26 C19 120.8(3) . . ?
C25 C26 C27 114.9(3) . . ?
C19 C26 C27 124.3(3) . . ?
C26 C27 H24 109.5 . . ?
C26 C27 H26 109.5 . . ?
H24 C27 H26 109.5 . . ?
C26 C27 H25 109.5 . . ?
H24 C27 H25 109.5 . . ?
H26 C27 H25 109.5 . . ?
N3 C28 C29 121.9(3) . . ?
N3 C28 H30 119.1 . . ?
C29 C28 H30 119.1 . . ?
C28 C29 C30 118.9(3) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C31 C30 C29 118.9(3) . . ?
C31 C30 H27 120.5 . . ?
C29 C30 H27 120.5 . . ?
C30 C31 C12 121.6(3) . . ?
C30 C31 H28 119.2 . . ?
C12 C31 H28 119.2 . . ?
C33 C32 C8 122.1(3) . . ?
C33 C32 H31 118.9 . . ?
C8 C32 H31 118.9 . . ?
C32 C33 C11 119.5(4) . . ?
C32 C33 H32 120.2 . . ?
C11 C33 H32 120.2 . . ?
N3 B1 C6 109.0(3) . . ?
N3 B1 C19 108.4(3) . . ?
C6 B1 C19 113.8(3) . . ?
N3 B1 Cl1 101.6(2) . . ?
C6 B1 Cl1 105.1(2) . . ?
C19 B1 Cl1 118.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 B2 C8 -112.0(4) . . . . ?
C13 N2 B2 C8 63.3(4) . . . . ?
C6 N2 B2 C12 10.1(5) . . . . ?
C13 N2 B2 C12 -174.7(3) . . . . ?
C6 N2 B2 Cl2 126.7(3) . . . . ?
C13 N2 B2 Cl2 -58.0(4) . . . . ?
C16 C2 C3 C4 -4.7(5) . . . . ?
C1 C2 C3 C4 175.4(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C3 C4 C15 178.3(3) . . . . ?
C3 C4 C5 C17 6.5(5) . . . . ?
C15 C4 C5 C17 -172.0(3) . . . . ?
C3 C4 C5 N1 -176.2(3) . . . . ?
C15 C4 C5 N1 5.3(5) . . . . ?
C6 N1 C5 C17 -86.7(4) . . . . ?
C14 N1 C5 C17 99.6(4) . . . . ?
C6 N1 C5 C4 95.9(4) . . . . ?
C14 N1 C5 C4 -77.8(4) . . . . ?
C13 N2 C6 N1 0.2(4) . . . . ?
B2 N2 C6 N1 176.0(3) . . . . ?
C13 N2 C6 B1 -177.4(3) . . . . ?
B2 N2 C6 B1 -1.5(5) . . . . ?
C14 N1 C6 N2 0.0(4) . . . . ?
C5 N1 C6 N2 -174.5(3) . . . . ?
C14 N1 C6 B1 177.4(3) . . . . ?
C5 N1 C6 B1 3.0(6) . . . . ?
N2 B2 C8 C32 49.9(4) . . . . ?
C12 B2 C8 C32 -72.3(4) . . . . ?
Cl2 B2 C8 C32 167.8(3) . . . . ?
N2 B2 C8 C9 -133.8(3) . . . . ?
C12 B2 C8 C9 104.0(4) . . . . ?
Cl2 B2 C8 C9 -16.0(4) . . . . ?
C32 C8 C9 C10 0.1(5) . . . . ?
B2 C8 C9 C10 -176.3(3) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C10 C11 C33 0.3(6) . . . . ?
C28 N3 C12 C31 2.9(5) . . . . ?
B1 N3 C12 C31 -174.9(3) . . . . ?
C28 N3 C12 B2 -174.8(3) . . . . ?
B1 N3 C12 B2 7.5(5) . . . . ?
N2 B2 C12 N3 -13.0(5) . . . . ?
C8 B2 C12 N3 109.2(4) . . . . ?
Cl2 B2 C12 N3 -128.5(3) . . . . ?
N2 B2 C12 C31 169.4(3) . . . . ?
C8 B2 C12 C31 -68.4(4) . . . . ?
Cl2 B2 C12 C31 53.9(4) . . . . ?
C6 N2 C13 C14 -0.3(4) . . . . ?
B2 N2 C13 C14 -176.2(3) . . . . ?
N2 C13 C14 N1 0.3(4) . . . . ?
C6 N1 C14 C13 -0.2(4) . . . . ?
C5 N1 C14 C13 174.5(3) . . . . ?
C3 C2 C16 C17 3.9(5) . . . . ?
C1 C2 C16 C17 -176.3(3) . . . . ?
C4 C5 C17 C16 -7.4(5) . . . . ?
N1 C5 C17 C16 175.4(3) . . . . ?
C4 C5 C17 C18 170.4(3) . . . . ?
N1 C5 C17 C18 -6.9(5) . . . . ?
C2 C16 C17 C5 2.0(5) . . . . ?
C2 C16 C17 C18 -175.8(3) . . . . ?
C26 C19 C20 C22 0.3(5) . . . . ?
B1 C19 C20 C22 -179.9(3) . . . . ?
C26 C19 C20 C21 -179.3(3) . . . . ?
B1 C19 C20 C21 0.5(5) . . . . ?
C19 C20 C22 C23 -0.3(5) . . . . ?
C21 C20 C22 C23 179.4(3) . . . . ?
C20 C22 C23 C25 -0.7(5) . . . . ?
C20 C22 C23 C24 179.5(3) . . . . ?
C22 C23 C25 C26 1.8(5) . . . . ?
C24 C23 C25 C26 -178.5(3) . . . . ?
C23 C25 C26 C19 -1.8(5) . . . . ?
C23 C25 C26 C27 178.6(3) . . . . ?
C20 C19 C26 C25 0.7(5) . . . . ?
B1 C19 C26 C25 -179.1(3) . . . . ?
C20 C19 C26 C27 -179.8(3) . . . . ?
B1 C19 C26 C27 0.4(5) . . . . ?
C12 N3 C28 C29 -3.4(5) . . . . ?
B1 N3 C28 C29 174.6(3) . . . . ?
N3 C28 C29 C30 0.9(5) . . . . ?
C28 C29 C30 C31 1.9(5) . . . . ?
C29 C30 C31 C12 -2.4(6) . . . . ?
N3 C12 C31 C30 0.0(5) . . . . ?
B2 C12 C31 C30 177.8(3) . . . . ?
C9 C8 C32 C33 0.4(5) . . . . ?
B2 C8 C32 C33 177.0(3) . . . . ?
C8 C32 C33 C11 -0.6(5) . . . . ?
C10 C11 C33 C32 0.3(6) . . . . ?
C12 N3 B1 C6 1.9(4) . . . . ?
C28 N3 B1 C6 -176.0(3) . . . . ?
C12 N3 B1 C19 126.2(3) . . . . ?
C28 N3 B1 C19 -51.7(4) . . . . ?
C12 N3 B1 Cl1 -108.8(3) . . . . ?
C28 N3 B1 Cl1 73.4(3) . . . . ?
N2 C6 B1 N3 -5.1(5) . . . . ?
N1 C6 B1 N3 177.9(3) . . . . ?
N2 C6 B1 C19 -126.2(3) . . . . ?
N1 C6 B1 C19 56.8(5) . . . . ?
N2 C6 B1 Cl1 103.2(3) . . . . ?
N1 C6 B1 Cl1 -73.8(4) . . . . ?
C20 C19 B1 N3 127.6(3) . . . . ?
C26 C19 B1 N3 -52.6(4) . . . . ?
C20 C19 B1 C6 -110.9(4) . . . . ?
C26 C19 B1 C6 68.9(4) . . . . ?
C20 C19 B1 Cl1 13.0(5) . . . . ?
C26 C19 B1 Cl1 -167.2(3) . . . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.097



_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# 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_cp030_a
_database_code_depnum_ccdc_archive 'CCDC 2331659'
loop_
_audit_author_name
_audit_author_address
'Brian Patrick'
;The University of British Columbia
Canada
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 B2 Cl3 N3'
_chemical_formula_weight         510.48

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/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                   15.6649(12)
_cell_length_b                   11.3864(9)
_cell_length_c                   15.8645(12)
_cell_angle_alpha                90
_cell_angle_beta                 115.787(2)
_cell_angle_gamma                90
_cell_volume                     2547.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.54

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.380
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7170
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51292
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.444
_diffrn_reflns_theta_max         30.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7806
_reflns_number_gt                6768
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0588P)²+2.5882P] 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         7806
_refine_ls_number_parameters     322
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
Cl03 Cl 0.58470(4) 0.40171(6) 0.59970(4) 0.02841(19) Uani 0.960(3) 1 d . . P A
1
Cl02 Cl 0.76814(5) 0.40961(6) 0.77815(5) 0.02480(15) Uani 0.960(3) 1 d . . P A
1
Cl3A Cl 0.5675(8) 0.4540(17) 0.5803(9) 0.026(3) Uiso 0.040(3) 1 d . . P A 2
Cl2A Cl 0.7448(16) 0.3783(19) 0.7537(16) 0.052(6) Uiso 0.040(3) 1 d D . P A 2
Cl01 Cl 0.54506(3) 0.81081(3) 0.57298(2) 0.01923(9) Uani 1 1 d . . . . .
N004 N 0.77134(9) 0.54298(12) 0.58412(9) 0.0165(2) Uani 1 1 d . . . . .
N005 N 0.62964(9) 0.57664(12) 0.73518(9) 0.0160(2) Uani 1 1 d . . . . .
N006 N 0.71685(9) 0.69562(11) 0.62737(9) 0.0160(2) Uani 1 1 d . . . . .
C007 C 0.72193(10) 0.57819(13) 0.63201(10) 0.0148(3) Uani 1 1 d . . . . .
C008 C 0.79799(11) 0.42416(13) 0.57308(11) 0.0165(3) Uani 1 1 d . . . . .
C009 C 0.73878(11) 0.36060(14) 0.49346(10) 0.0176(3) Uani 1 1 d . . . . .
C00A C 0.73439(10) 0.88353(13) 0.72615(10) 0.0145(3) Uani 1 1 d . . . . .
C00B C 0.63234(11) 0.69564(13) 0.73726(10) 0.0155(3) Uani 1 1 d . . . . .
C00C C 0.87301(11) 0.95157(15) 0.86551(11) 0.0191(3) Uani 1 1 d . . . . .
H00A H 0.922922 0.934189 0.923166 0.023 Uiso 1 1 calc R U . . .
C00D C 0.58986(11) 0.51483(15) 0.78313(11) 0.0199(3) Uani 1 1 d . . . . .
H00B H 0.587488 0.433329 0.778904 0.024 Uiso 1 1 calc R U . . .
C00E C 0.76498(12) 0.24536(14) 0.48585(11) 0.0209(3) Uani 1 1 d . . . . .
H00C H 0.726206 0.200822 0.434179 0.025 Uiso 1 1 calc R U . . .
C00F C 0.81238(11) 0.86074(14) 0.81389(10) 0.0175(3) Uani 1 1 d . . . . .
C00G C 0.72588(11) 1.00050(13) 0.69163(11) 0.0166(3) Uani 1 1 d . . . . .
C00H C 0.76259(12) 0.73574(14) 0.57536(11) 0.0208(3) Uani 1 1 d . . . . .
H00D H 0.769104 0.813721 0.561715 0.025 Uiso 1 1 calc R U . . .
C00I C 0.78771(11) 1.08820(14) 0.74599(12) 0.0198(3) Uani 1 1 d . . . . .
H00E H 0.779330 1.164338 0.722510 0.024 Uiso 1 1 calc R U . . .
C00J C 0.83810(12) 0.73751(15) 0.85606(12) 0.0224(3) Uani 1 1 d . . . . .
H00F H 0.834530 0.683097 0.808413 0.034 Uiso 1 1 calc R U . . .
H00G H 0.794511 0.714136 0.880680 0.034 Uiso 1 1 calc R U . . .
H00H H 0.901375 0.738031 0.905524 0.034 Uiso 1 1 calc R U . . .
C00K C 0.65160(12) 0.41373(16) 0.41621(12) 0.0241(3) Uani 1 1 d . . . . .
H00I H 0.624296 0.470139 0.442334 0.036 Uiso 1 1 calc R U . . .
H00J H 0.606235 0.352941 0.385267 0.036 Uiso 1 1 calc R U . . .
H00K H 0.668816 0.451914 0.371864 0.036 Uiso 1 1 calc R U . . .
C00L C 0.55359(13) 0.56959(17) 0.83697(12) 0.0243(3) Uani 1 1 d . . . . .
H00L H 0.526724 0.526151 0.868956 0.029 Uiso 1 1 calc R U . . .
C00M C 0.90665(12) 0.26407(15) 0.62897(12) 0.0223(3) Uani 1 1 d . . . . .
H00M H 0.963079 0.232098 0.673042 0.027 Uiso 1 1 calc R U . . .
C00N C 0.88364(11) 0.37953(15) 0.64042(11) 0.0190(3) Uani 1 1 d . . . . .
C00O C 0.79603(12) 0.64086(14) 0.54804(12) 0.0210(3) Uani 1 1 d . . . . .
H00N H 0.829379 0.641317 0.511791 0.025 Uiso 1 1 calc R U . . .
C00P C 0.59573(12) 0.75371(15) 0.79259(11) 0.0206(3) Uani 1 1 d . . . . .
H00O H 0.597208 0.835316 0.795271 0.025 Uiso 1 1 calc R U . . .
C00Q C 0.55753(13) 0.69192(17) 0.84319(12) 0.0243(3) Uani 1 1 d . . . . .
H00P H 0.534857 0.731248 0.880703 0.029 Uiso 1 1 calc R U . . .
C00R C 0.84737(13) 0.19515(15) 0.55322(12) 0.0230(3) Uani 1 1 d . . . . .
C00S C 0.86103(12) 1.06632(15) 0.83346(12) 0.0206(3) Uani 1 1 d . . . . .
C00T C 0.95057(12) 0.45138(17) 0.72254(12) 0.0252(3) Uani 1 1 d . . . . .
H00Q H 0.947751 0.532121 0.704085 0.038 Uiso 1 1 calc R U . . .
H00R H 1.014048 0.422547 0.742826 0.038 Uiso 1 1 calc R U . . .
H00S H 0.932505 0.445181 0.772950 0.038 Uiso 1 1 calc R U . . .
C00U C 0.65574(12) 1.04001(15) 0.59501(12) 0.0224(3) Uani 1 1 d . . . . .
H00T H 0.659901 0.989001 0.548755 0.034 Uiso 1 1 calc R U . . .
H00U H 0.670160 1.119004 0.584393 0.034 Uiso 1 1 calc R U . . .
H00V H 0.592693 1.037052 0.590631 0.034 Uiso 1 1 calc R U . . .
C00V C 0.92833(13) 1.16207(16) 0.88983(14) 0.0283(4) Uani 1 1 d . . . . .
H00W H 0.912661 1.233802 0.854512 0.042 Uiso 1 1 calc R U . . .
H00X H 0.992139 1.139812 0.903506 0.042 Uiso 1 1 calc R U . . .
H00Y H 0.922996 1.173480 0.947302 0.042 Uiso 1 1 calc R U . . .
C00W C 0.87245(17) 0.06916(17) 0.54521(15) 0.0355(4) Uani 1 1 d . . . . .
H00Z H 0.937170 0.064748 0.554553 0.053 Uiso 1 1 calc R U . . .
H01A H 0.831578 0.039752 0.484110 0.053 Uiso 1 1 calc R U . . .
H01B H 0.864574 0.022740 0.591851 0.053 Uiso 1 1 calc R U . . .
B1 B 0.66651(12) 0.77407(15) 0.67213(11) 0.0152(3) Uani 1 1 d . . . . .
B2 B 0.67552(12) 0.49874(15) 0.68373(12) 0.0170(3) Uani 1 1 d 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
Cl03 B2 1.8362(18) . ?
Cl02 B2 1.8676(19) . ?
Cl3A B2 1.844(12) . ?
Cl2A B2 1.800(13) . ?
Cl01 B1 1.9144(17) . ?
N004 C007 1.3596(18) . ?
N004 C00O 1.383(2) . ?
N004 C008 1.4488(19) . ?
N005 C00B 1.356(2) . ?
N005 C00D 1.3693(19) . ?
N005 B2 1.575(2) . ?
N006 C007 1.3396(19) . ?
N006 C00H 1.3846(19) . ?
N006 B1 1.553(2) . ?
C007 B2 1.593(2) . ?
C008 C00N 1.397(2) . ?
C008 C009 1.400(2) . ?
C009 C00E 1.396(2) . ?
C009 C00K 1.509(2) . ?
C00A C00F 1.421(2) . ?
C00A C00G 1.424(2) . ?
C00A B1 1.620(2) . ?
C00B C00P 1.405(2) . ?
C00B B1 1.623(2) . ?
C00C C00S 1.385(2) . ?
C00C C00F 1.402(2) . ?
C00D C00L 1.365(2) . ?
C00E C00R 1.391(2) . ?
C00F C00J 1.531(2) . ?
C00G C00I 1.397(2) . ?
C00G C00U 1.515(2) . ?
C00H C00O 1.352(2) . ?
C00I C00S 1.386(2) . ?
C00L C00Q 1.396(3) . ?
C00M C00N 1.396(2) . ?
C00M C00R 1.397(2) . ?
C00N C00T 1.509(2) . ?
C00P C00Q 1.384(2) . ?
C00R C00W 1.507(2) . ?
C00S C00V 1.510(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
C007 N004 C00O 108.87(13) . . ?
C007 N004 C008 127.36(13) . . ?
C00O N004 C008 123.74(12) . . ?
C00B N005 C00D 121.14(13) . . ?
C00B N005 B2 124.00(12) . . ?
C00D N005 B2 114.78(13) . . ?
C007 N006 C00H 109.17(13) . . ?
C007 N006 B1 125.37(12) . . ?
C00H N006 B1 125.46(13) . . ?
N006 C007 N004 107.35(13) . . ?
N006 C007 B2 124.44(13) . . ?
N004 C007 B2 128.21(13) . . ?
C00N C008 C009 122.73(14) . . ?
C00N C008 N004 118.59(14) . . ?
C009 C008 N004 118.63(14) . . ?
C00E C009 C008 117.37(14) . . ?
C00E C009 C00K 120.19(14) . . ?
C008 C009 C00K 122.40(14) . . ?
C00F C00A C00G 116.39(14) . . ?
C00F C00A B1 117.68(13) . . ?
C00G C00A B1 125.86(13) . . ?
N005 C00B C00P 117.95(14) . . ?
N005 C00B B1 123.37(13) . . ?
C00P C00B B1 118.43(13) . . ?
C00S C00C C00F 122.17(15) . . ?
C00L C00D N005 121.79(16) . . ?
C00R C00E C009 121.97(15) . . ?
C00C C00F C00A 120.86(14) . . ?
C00C C00F C00J 115.99(14) . . ?
C00A C00F C00J 123.11(14) . . ?
C00I C00G C00A 120.48(14) . . ?
C00I C00G C00U 114.54(14) . . ?
C00A C00G C00U 124.91(14) . . ?
C00O C00H N006 107.49(14) . . ?
C00S C00I C00G 122.65(15) . . ?
C00D C00L C00Q 118.83(15) . . ?
C00N C00M C00R 121.90(15) . . ?
C00M C00N C008 117.35(15) . . ?
C00M C00N C00T 120.08(15) . . ?
C008 C00N C00T 122.57(15) . . ?
C00H C00O N004 107.11(13) . . ?
C00Q C00P C00B 121.33(16) . . ?
C00P C00Q C00L 118.91(15) . . ?
C00E C00R C00M 118.52(15) . . ?
C00E C00R C00W 121.01(17) . . ?
C00M C00R C00W 120.47(16) . . ?
C00C C00S C00I 117.27(15) . . ?
C00C C00S C00V 121.04(16) . . ?
C00I C00S C00V 121.62(16) . . ?
N006 B1 C00A 109.71(12) . . ?
N006 B1 C00B 110.39(12) . . ?
C00A B1 C00B 114.14(12) . . ?
N006 B1 Cl01 105.71(10) . . ?
C00A B1 Cl01 117.09(11) . . ?
C00B B1 Cl01 99.11(10) . . ?
N005 B2 C007 111.13(13) . . ?
N005 B2 Cl2A 113.5(8) . . ?
C007 B2 Cl2A 117.5(8) . . ?
N005 B2 Cl03 109.33(11) . . ?
C007 B2 Cl03 110.53(11) . . ?
N005 B2 Cl3A 99.7(4) . . ?
C007 B2 Cl3A 98.4(5) . . ?
Cl2A B2 Cl3A 114.3(9) . . ?
N005 B2 Cl02 105.12(10) . . ?
C007 B2 Cl02 110.62(11) . . ?
Cl03 B2 Cl02 109.97(9) . . ?

_refine_diff_density_max         1.411
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.075



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
####################################################################### 
# 
# 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_vpn049
_database_code_depnum_ccdc_archive 'CCDC 2331655'
loop_
_audit_author_name
_audit_author_address
'Brian Patrick'
;The University of British Columbia
Canada
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H31 B I N3'
_chemical_formula_weight         535.26

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'
I I -0.4742 1.8119 '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                   8.0398(6)
_cell_length_b                   28.378(2)
_cell_length_c                   11.9315(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.797(2)
_cell_angle_gamma                90
_cell_volume                     2577.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      30.40

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    1.261
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82821
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.435
_diffrn_reflns_theta_max         30.614
_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             7912
_reflns_number_gt                6300
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0241P)²+2.8427P] 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         7912
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
I1_1 I 0.00118(2) 0.70339(2) 0.18910(2) 0.01870(4) Uani 1 1 d . . . . .
N1_2 N 0.5196(2) 0.65354(6) 0.87488(15) 0.0134(3) Uani 1 1 d . . . . .
C1_2 C 0.5867(3) 0.65235(8) 0.99374(19) 0.0177(4) Uani 1 1 d . . . . .
H1_2 H 0.6986 0.6402 1.0298 0.021 Uiso 1 1 calc R U . . .
B1_2 B 0.6163(3) 0.63610(9) 0.7799(2) 0.0143(4) Uani 1 1 d . . . . .
N2_2 N 0.3202(2) 0.67069(6) 0.70056(16) 0.0146(3) Uani 1 1 d . . . . .
C2_2 C 0.4907(3) 0.66907(9) 1.0624(2) 0.0220(5) Uani 1 1 d . . . . .
H2_2 H 0.5368 0.6675 1.1445 0.026 Uiso 1 1 calc R U . . .
N3_2 N 0.3925(2) 0.65070(6) 0.54938(16) 0.0150(4) Uani 1 1 d . . . . .
C3_2 C 0.3252(3) 0.68817(8) 1.0091(2) 0.0201(5) Uani 1 1 d . . . . .
H3_2 H 0.2596 0.6990 1.0554 0.024 Uiso 1 1 calc R U . . .
C4_2 C 0.2572(3) 0.69114(7) 0.8862(2) 0.0169(4) Uani 1 1 d . . . . .
H4_2 H 0.1481 0.7046 0.8483 0.020 Uiso 1 1 calc R U . . .
C5_2 C 0.3598(3) 0.67307(7) 0.82388(18) 0.0138(4) Uani 1 1 d . . . . .
C6_2 C 0.4490(3) 0.64984(7) 0.66761(18) 0.0131(4) Uani 1 1 d . . . . .
C7_2 C 0.1811(3) 0.68458(8) 0.6032(2) 0.0196(5) Uani 1 1 d . . . . .
H7_2 H 0.0780 0.6994 0.6033 0.024 Uiso 1 1 calc R U . . .
C8_2 C 0.2270(3) 0.67205(8) 0.5077(2) 0.0198(5) Uani 1 1 d . . . . .
H8_2 H 0.1607 0.6768 0.4288 0.024 Uiso 1 1 calc R U . . .
C9_2 C 0.7708(3) 0.67500(9) 0.7980(2) 0.0222(5) Uani 1 1 d . . . . .
H9A_2 H 0.8138 0.6740 0.7318 0.033 Uiso 1 1 calc R U . . .
H9B_2 H 0.8651 0.6682 0.8694 0.033 Uiso 1 1 calc R U . . .
H9C_2 H 0.7248 0.7058 0.8036 0.033 Uiso 1 1 calc R U . . .
C10_2 C 0.6686(3) 0.58044(8) 0.79811(18) 0.0146(4) Uani 1 1 d . . . . .
C11_2 C 0.8187(3) 0.56204(8) 0.77538(19) 0.0178(4) Uani 1 1 d . . . . .
C12_2 C 0.8743(3) 0.51598(8) 0.8075(2) 0.0220(5) Uani 1 1 d . . . . .
H12_2 H 0.9749 0.5052 0.7933 0.026 Uiso 1 1 calc R U . . .
C13_2 C 0.7859(3) 0.48553(8) 0.8598(2) 0.0235(5) Uani 1 1 d . . . . .
C14_2 C 0.6307(3) 0.50206(8) 0.8727(2) 0.0219(5) Uani 1 1 d . . . . .
H14_2 H 0.5650 0.4820 0.9035 0.026 Uiso 1 1 calc R U . . .
C15_2 C 0.5696(3) 0.54767(8) 0.8410(2) 0.0176(4) Uani 1 1 d . . . . .
C16_2 C 0.4926(3) 0.63211(8) 0.47750(18) 0.0156(4) Uani 1 1 d . . . . .
C17_2 C 0.4729(3) 0.58465(8) 0.4467(2) 0.0196(5) Uani 1 1 d . . . . .
C18_2 C 0.5757(3) 0.56733(8) 0.3817(2) 0.0225(5) Uani 1 1 d . . . . .
H18_2 H 0.5644 0.5358 0.3589 0.027 Uiso 1 1 calc R U . . .
C19_2 C 0.6940(3) 0.59538(9) 0.3498(2) 0.0214(5) Uani 1 1 d . . . . .
C20_2 C 0.7071(3) 0.64291(8) 0.38088(19) 0.0193(4) Uani 1 1 d . . . . .
H20_2 H 0.7855 0.6620 0.3591 0.023 Uiso 1 1 calc R U . . .
C21_2 C 0.6045(3) 0.66235(8) 0.44420(18) 0.0169(4) Uani 1 1 d . . . . .
C22_2 C 0.9226(3) 0.58950(9) 0.7114(2) 0.0248(5) Uani 1 1 d . . . . .
H22A_2 H 0.9875 0.5680 0.6792 0.037 Uiso 1 1 calc R U . . .
H22B_2 H 1.0026 0.6104 0.7660 0.037 Uiso 1 1 calc R U . . .
H22C_2 H 0.8434 0.6075 0.6484 0.037 Uiso 1 1 calc R U . . .
C23_2 C 0.8516(4) 0.43606(9) 0.8954(3) 0.0350(7) Uani 1 1 d . . . . .
H23A_2 H 0.8204 0.4162 0.8265 0.053 Uiso 1 1 calc R U . . .
H23B_2 H 0.7992 0.4240 0.9513 0.053 Uiso 1 1 calc R U . . .
H23C_2 H 0.9771 0.4365 0.9308 0.053 Uiso 1 1 calc R U . . .
C24_2 C 0.3873(3) 0.55883(8) 0.8464(2) 0.0233(5) Uani 1 1 d . . . . .
H24A_2 H 0.3238 0.5771 0.7784 0.035 Uiso 1 1 calc R U . . .
H24B_2 H 0.3976 0.5764 0.9171 0.035 Uiso 1 1 calc R U . . .
H24C_2 H 0.3253 0.5300 0.8472 0.035 Uiso 1 1 calc R U . . .
C25_2 C 0.3453(4) 0.55382(9) 0.4816(2) 0.0295(6) Uani 1 1 d . . . . .
H25A_2 H 0.2324 0.5689 0.4594 0.044 Uiso 1 1 calc R U . . .
H25B_2 H 0.3870 0.5490 0.5657 0.044 Uiso 1 1 calc R U . . .
H25C_2 H 0.3352 0.5240 0.4420 0.044 Uiso 1 1 calc R U . . .
C26_2 C 0.8066(4) 0.57537(10) 0.2815(2) 0.0316(6) Uani 1 1 d . . . . .
H26A_2 H 0.7328 0.5650 0.2051 0.047 Uiso 1 1 calc R U . . .
H26B_2 H 0.8729 0.5491 0.3241 0.047 Uiso 1 1 calc R U . . .
H26C_2 H 0.8857 0.5992 0.2720 0.047 Uiso 1 1 calc R U . . .
C27_2 C 0.6137(4) 0.71424(8) 0.4722(2) 0.0258(5) Uani 1 1 d . . . . .
H27A_2 H 0.7095 0.7281 0.4525 0.039 Uiso 1 1 calc R U . . .
H27B_2 H 0.6317 0.7186 0.5551 0.039 Uiso 1 1 calc R U . . .
H27C_2 H 0.5057 0.7291 0.4268 0.039 Uiso 1 1 calc R U . . .


_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
N1_2 C1_2 1.345(3) . ?
N1_2 C5_2 1.351(3) . ?
N1_2 B1_2 1.643(3) . ?
C1_2 C2_2 1.379(3) . ?
B1_2 C6_2 1.611(3) . ?
B1_2 C9_2 1.623(3) . ?
B1_2 C10_2 1.631(3) . ?
N2_2 C6_2 1.356(3) . ?
N2_2 C7_2 1.385(3) . ?
N2_2 C5_2 1.403(3) . ?
C2_2 C3_2 1.387(3) . ?
N3_2 C6_2 1.336(3) . ?
N3_2 C8_2 1.399(3) . ?
N3_2 C16_2 1.451(3) . ?
C3_2 C4_2 1.392(3) . ?
C4_2 C5_2 1.376(3) . ?
C7_2 C8_2 1.353(3) . ?
C10_2 C11_2 1.419(3) . ?
C10_2 C15_2 1.422(3) . ?
C11_2 C12_2 1.395(3) . ?
C11_2 C22_2 1.516(3) . ?
C12_2 C13_2 1.389(3) . ?
C13_2 C14_2 1.387(3) . ?
C13_2 C23_2 1.512(3) . ?
C14_2 C15_2 1.393(3) . ?
C15_2 C24_2 1.522(3) . ?
C16_2 C21_2 1.390(3) . ?
C16_2 C17_2 1.392(3) . ?
C17_2 C18_2 1.392(3) . ?
C17_2 C25_2 1.506(3) . ?
C18_2 C19_2 1.385(3) . ?
C19_2 C20_2 1.394(3) . ?
C19_2 C26_2 1.510(3) . ?
C20_2 C21_2 1.400(3) . ?
C21_2 C27_2 1.506(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
C1_2 N1_2 C5_2 119.02(19) . . ?
C1_2 N1_2 B1_2 126.97(18) . . ?
C5_2 N1_2 B1_2 113.91(17) . . ?
N1_2 C1_2 C2_2 120.4(2) . . ?
C6_2 B1_2 C9_2 110.14(18) . . ?
C6_2 B1_2 C10_2 117.10(18) . . ?
C9_2 B1_2 C10_2 119.18(19) . . ?
C6_2 B1_2 N1_2 92.69(16) . . ?
C9_2 B1_2 N1_2 102.41(17) . . ?
C10_2 B1_2 N1_2 111.01(17) . . ?
C6_2 N2_2 C7_2 111.49(18) . . ?
C6_2 N2_2 C5_2 112.86(17) . . ?
C7_2 N2_2 C5_2 135.64(19) . . ?
C1_2 C2_2 C3_2 120.0(2) . . ?
C6_2 N3_2 C8_2 110.11(18) . . ?
C6_2 N3_2 C16_2 123.56(18) . . ?
C8_2 N3_2 C16_2 126.33(18) . . ?
C2_2 C3_2 C4_2 120.0(2) . . ?
C5_2 C4_2 C3_2 116.5(2) . . ?
N1_2 C5_2 C4_2 124.0(2) . . ?
N1_2 C5_2 N2_2 108.31(18) . . ?
C4_2 C5_2 N2_2 127.7(2) . . ?
N3_2 C6_2 N2_2 105.47(18) . . ?
N3_2 C6_2 B1_2 142.3(2) . . ?
N2_2 C6_2 B1_2 112.05(18) . . ?
C8_2 C7_2 N2_2 105.4(2) . . ?
C7_2 C8_2 N3_2 107.51(19) . . ?
C11_2 C10_2 C15_2 115.9(2) . . ?
C11_2 C10_2 B1_2 121.98(19) . . ?
C15_2 C10_2 B1_2 122.09(19) . . ?
C12_2 C11_2 C10_2 120.6(2) . . ?
C12_2 C11_2 C22_2 116.1(2) . . ?
C10_2 C11_2 C22_2 123.2(2) . . ?
C13_2 C12_2 C11_2 122.8(2) . . ?
C14_2 C13_2 C12_2 116.7(2) . . ?
C14_2 C13_2 C23_2 121.9(2) . . ?
C12_2 C13_2 C23_2 121.3(2) . . ?
C13_2 C14_2 C15_2 122.4(2) . . ?
C14_2 C15_2 C10_2 121.1(2) . . ?
C14_2 C15_2 C24_2 116.2(2) . . ?
C10_2 C15_2 C24_2 122.5(2) . . ?
C21_2 C16_2 C17_2 123.4(2) . . ?
C21_2 C16_2 N3_2 118.52(19) . . ?
C17_2 C16_2 N3_2 118.1(2) . . ?
C16_2 C17_2 C18_2 116.8(2) . . ?
C16_2 C17_2 C25_2 121.2(2) . . ?
C18_2 C17_2 C25_2 121.9(2) . . ?
C19_2 C18_2 C17_2 122.3(2) . . ?
C18_2 C19_2 C20_2 118.9(2) . . ?
C18_2 C19_2 C26_2 121.1(2) . . ?
C20_2 C19_2 C26_2 120.0(2) . . ?
C19_2 C20_2 C21_2 121.2(2) . . ?
C16_2 C21_2 C20_2 117.3(2) . . ?
C16_2 C21_2 C27_2 122.0(2) . . ?
C20_2 C21_2 C27_2 120.6(2) . . ?

_refine_diff_density_max         0.849
_refine_diff_density_min         -1.343
_refine_diff_density_rms         0.094



_exptl_crystal_recrystallization_method 'DCM/Ether layering'
