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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_193_2
_database_code_depnum_ccdc_archive 'CCDC 2113561'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        a
_chemical_formula_moiety         'C10 H9 B N2'
_chemical_formula_sum            'C10 H9 B N2'
_chemical_formula_weight         168.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.8712(2)
_cell_length_b                   11.4894(3)
_cell_length_c                   9.7181(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.9734(7)
_cell_angle_gamma                90
_cell_volume                     897.91(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.24
_cell_measurement_theta_min      5.02
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0844 before and 0.0491 after correction.
The Ratio of minimum to maximum transmission is 0.8992.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13328
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.949
_diffrn_reflns_theta_min         5.501
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1835
_reflns_number_total             1922
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.2637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0858
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.15802(10) 0.94312(7) 0.33014(10) 0.0281(2) Uani 1 1 d . . . . .
C2 C 0.17430(11) 0.84885(8) 0.37362(10) 0.0221(2) Uani 1 1 d . . . . .
B3 B 0.19108(13) 0.71849(9) 0.43470(13) 0.0231(2) Uani 1 1 d . . . . .
H3A H 0.2516(14) 0.7181(10) 0.5623(14) 0.028(3) Uiso 1 1 d . . . . .
H3B H 0.0662(15) 0.6768(11) 0.3881(14) 0.031(3) Uiso 1 1 d . . . . .
N4 N 0.30180(9) 0.64465(6) 0.37323(8) 0.01833(18) Uani 1 1 d . . . . .
C5 C 0.22992(11) 0.55828(8) 0.27663(10) 0.0219(2) Uani 1 1 d . . . . .
H5 H 0.114071 0.545727 0.244018 0.026 Uiso 1 1 calc R U . . .
C6 C 0.31732(12) 0.48501(8) 0.22080(10) 0.0242(2) Uani 1 1 d . . . . .
H6 H 0.260959 0.425133 0.150402 0.029 Uiso 1 1 calc R U . . .
C7 C 0.48453(12) 0.50055(8) 0.26864(10) 0.0233(2) Uani 1 1 d . . . . .
H7 H 0.545742 0.450896 0.232708 0.028 Uiso 1 1 calc R U . . .
C8 C 0.56582(11) 0.59103(8) 0.37199(10) 0.0193(2) Uani 1 1 d . . . . .
C9 C 0.47070(10) 0.66457(7) 0.42251(9) 0.01746(19) Uani 1 1 d . . . . .
C10 C 0.54954(11) 0.75662(8) 0.52360(10) 0.0201(2) Uani 1 1 d . . . . .
H10 H 0.486626 0.806842 0.556972 0.024 Uiso 1 1 calc R U . . .
C11 C 0.71774(11) 0.77318(8) 0.57345(10) 0.0227(2) Uani 1 1 d . . . . .
H11 H 0.770419 0.835343 0.641245 0.027 Uiso 1 1 calc R U . . .
C12 C 0.81343(11) 0.69951(9) 0.52570(11) 0.0242(2) Uani 1 1 d . . . . .
H12 H 0.929806 0.711855 0.562263 0.029 Uiso 1 1 calc R U . . .
C13 C 0.73961(11) 0.61043(8) 0.42710(10) 0.0229(2) Uani 1 1 d . . . . .
H13 H 0.804859 0.561198 0.395217 0.027 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 C2 1.1493(13) . ?
C2 B3 1.5947(14) . ?
B3 H3A 1.124(12) . ?
B3 H3B 1.113(12) . ?
B3 N4 1.5927(12) . ?
N4 C5 1.3293(12) . ?
N4 C9 1.3860(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.3997(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3660(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.4134(13) . ?
C8 C9 1.4201(12) . ?
C8 C13 1.4200(13) . ?
C9 C10 1.4117(12) . ?
C10 H10 0.9500 . ?
C10 C11 1.3737(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.4089(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.3655(14) . ?
C13 H13 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
N1 C2 B3 178.01(10) . . ?
C2 B3 H3A 109.9(6) . . ?
C2 B3 H3B 109.4(6) . . ?
H3A B3 H3B 112.1(9) . . ?
N4 B3 C2 109.64(7) . . ?
N4 B3 H3A 109.2(6) . . ?
N4 B3 H3B 106.5(6) . . ?
C5 N4 B3 118.34(8) . . ?
C5 N4 C9 119.57(8) . . ?
C9 N4 B3 122.03(7) . . ?
N4 C5 H5 118.5 . . ?
N4 C5 C6 122.93(9) . . ?
C6 C5 H5 118.5 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.28(8) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.53(9) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 118.94(8) . . ?
C7 C8 C13 122.04(8) . . ?
C13 C8 C9 119.02(8) . . ?
N4 C9 C8 119.72(8) . . ?
N4 C9 C10 120.66(8) . . ?
C10 C9 C8 119.62(8) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.63(8) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.09(9) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.29(8) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.33(8) . . ?
C12 C13 H13 119.8 . . ?

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
C2 B3 N4 C5 -113.99(9) . . . . ?
C2 B3 N4 C9 68.91(10) . . . . ?
B3 N4 C5 C6 -177.23(8) . . . . ?
B3 N4 C9 C8 175.68(7) . . . . ?
B3 N4 C9 C10 -3.72(12) . . . . ?
N4 C5 C6 C7 1.17(14) . . . . ?
N4 C9 C10 C11 178.61(8) . . . . ?
C5 N4 C9 C8 -1.39(12) . . . . ?
C5 N4 C9 C10 179.21(8) . . . . ?
C5 C6 C7 C8 -0.77(14) . . . . ?
C6 C7 C8 C9 -0.62(13) . . . . ?
C6 C7 C8 C13 179.21(8) . . . . ?
C7 C8 C9 N4 1.72(12) . . . . ?
C7 C8 C9 C10 -178.87(8) . . . . ?
C7 C8 C13 C12 179.33(8) . . . . ?
C8 C9 C10 C11 -0.79(13) . . . . ?
C9 N4 C5 C6 -0.06(13) . . . . ?
C9 C8 C13 C12 -0.83(13) . . . . ?
C9 C10 C11 C12 -0.18(14) . . . . ?
C10 C11 C12 C13 0.66(14) . . . . ?
C11 C12 C13 C8 -0.14(14) . . . . ?
C13 C8 C9 N4 -178.12(7) . . . . ?
C13 C8 C9 C10 1.29(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_N2_163_1
_database_code_depnum_ccdc_archive 'CCDC 2113563'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 B N4'
_chemical_formula_sum            'C21 H15 B N4'
_chemical_formula_weight         334.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6002(3)
_cell_length_b                   9.8523(3)
_cell_length_c                   10.4405(3)
_cell_angle_alpha                112.050(2)
_cell_angle_beta                 100.947(2)
_cell_angle_gamma                100.116(2)
_cell_volume                     864.90(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8102
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      77.890
_cell_measurement_theta_min      4.761
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.743
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.529682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 31922 reflections, Rint = 0.1189
 (20589 with I > 3sig(I), Rint = 0.1141)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3671
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.873
_diffrn_reflns_theta_min         4.761
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CPAD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3281
_reflns_number_total             3671
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0868P)²+0.3074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.92491(15) 0.88856(16) 0.58327(15) 0.0301(3) Uani 1 1 d . . . . .
C2 C 0.82815(16) 0.78796(16) 0.56144(14) 0.0212(3) Uani 1 1 d . . . . .
B3 B 0.70126(18) 0.64573(18) 0.53563(16) 0.0201(3) Uani 1 1 d . . . . .
H3A H 0.673(2) 0.664(2) 0.639(2) 0.027(5) Uiso 1 1 d . . . . .
H3B H 0.736(2) 0.540(2) 0.493(2) 0.033(5) Uiso 1 1 d . . . . .
N4 N 0.55858(13) 0.63001(13) 0.41965(12) 0.0179(3) Uani 1 1 d . . . . .
N5 N 0.52444(13) 0.51981(13) 0.28904(12) 0.0185(3) Uani 1 1 d . . . . .
N6 N 0.39739(13) 0.52496(13) 0.21525(12) 0.0175(3) Uani 1 1 d . . . . .
C7 C 0.34577(16) 0.63848(15) 0.29877(14) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.45293(15) 0.70837(15) 0.43157(14) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.43663(16) 0.83307(16) 0.54709(15) 0.0202(3) Uani 1 1 d . . . . .
C10 C 0.30629(17) 0.87332(17) 0.51793(16) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.289963 0.955956 0.591902 0.030 Uiso 1 1 calc R U . . .
C11 C 0.19759(17) 0.79820(17) 0.38488(16) 0.0258(3) Uani 1 1 d . . . . .
H11 H 0.110107 0.830156 0.372984 0.031 Uiso 1 1 calc R U . . .
C12 C 0.21417(16) 0.67959(16) 0.27120(15) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.141701 0.629111 0.180514 0.027 Uiso 1 1 calc R U . . .
C13 C 0.32963(15) 0.41682(15) 0.06861(14) 0.0178(3) Uani 1 1 d . . . . .
C14 C 0.31488(15) 0.26339(15) 0.03277(14) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.351305 0.229842 0.103491 0.023 Uiso 1 1 calc R U . . .
C15 C 0.24544(16) 0.15996(15) -0.10930(15) 0.0208(3) Uani 1 1 d . . . . .
H15 H 0.234371 0.054384 -0.136269 0.025 Uiso 1 1 calc R U . . .
C16 C 0.19202(16) 0.20986(16) -0.21229(15) 0.0203(3) Uani 1 1 d . . . . .
H16 H 0.144300 0.138325 -0.308991 0.024 Uiso 1 1 calc R U . . .
C17 C 0.20839(16) 0.36420(16) -0.17387(15) 0.0214(3) Uani 1 1 d . . . . .
H17 H 0.172026 0.398013 -0.244401 0.026 Uiso 1 1 calc R U . . .
C18 C 0.27803(16) 0.46934(15) -0.03215(15) 0.0214(3) Uani 1 1 d . . . . .
H18 H 0.289923 0.575051 -0.005058 0.026 Uiso 1 1 calc R U . . .
C19 C 0.54374(16) 0.91714(16) 0.68349(15) 0.0207(3) Uani 1 1 d . . . . .
C20 C 0.62693(16) 0.99996(16) 0.80035(15) 0.0209(3) Uani 1 1 d . . . . .
C21 C 0.72304(16) 1.09829(15) 0.94108(15) 0.0191(3) Uani 1 1 d . . . . .
C22 C 0.87644(17) 1.12804(18) 0.97015(16) 0.0259(3) Uani 1 1 d . . . . .
H22 H 0.919725 1.082807 0.895747 0.031 Uiso 1 1 calc R U . . .
C23 C 0.96500(18) 1.22412(19) 1.10849(18) 0.0304(4) Uani 1 1 d . . . . .
H23 H 1.069118 1.243993 1.128368 0.036 Uiso 1 1 calc R U . . .
C24 C 0.90323(18) 1.29137(17) 1.21794(16) 0.0275(4) Uani 1 1 d . . . . .
H24 H 0.965004 1.357614 1.311909 0.033 Uiso 1 1 calc R U . . .
C25 C 0.75131(17) 1.26196(16) 1.19025(15) 0.0224(3) Uani 1 1 d . . . . .
H25 H 0.708834 1.307340 1.265299 0.027 Uiso 1 1 calc R U . . .
C26 C 0.66159(16) 1.16609(15) 1.05264(15) 0.0202(3) Uani 1 1 d . . . . .
H26 H 0.557541 1.146168 1.033788 0.024 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 C2 1.151(2) . ?
C2 B3 1.585(2) . ?
B3 H3A 1.121(19) . ?
B3 H3B 1.11(2) . ?
B3 N4 1.5878(19) . ?
N4 N5 1.3188(15) . ?
N4 C8 1.3752(18) . ?
N5 N6 1.3334(16) . ?
N6 C7 1.3724(18) . ?
N6 C13 1.4338(16) . ?
C7 C8 1.3956(18) . ?
C7 C12 1.404(2) . ?
C8 C9 1.4196(19) . ?
C9 C10 1.391(2) . ?
C9 C19 1.4249(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.405(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3875(19) . ?
C13 C18 1.386(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.3906(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.3927(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.202(2) . ?
C20 C21 1.4321(18) . ?
C21 C22 1.400(2) . ?
C21 C26 1.402(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.3869(19) . ?
C26 H26 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
N1 C2 B3 176.77(15) . . ?
C2 B3 H3A 108.9(10) . . ?
C2 B3 H3B 110.5(10) . . ?
C2 B3 N4 109.47(11) . . ?
H3A B3 H3B 111.5(15) . . ?
N4 B3 H3A 108.6(10) . . ?
N4 B3 H3B 107.9(10) . . ?
N5 N4 B3 118.38(11) . . ?
N5 N4 C8 110.44(11) . . ?
C8 N4 B3 131.07(11) . . ?
N4 N5 N6 106.98(11) . . ?
N5 N6 C7 111.47(11) . . ?
N5 N6 C13 120.41(11) . . ?
C7 N6 C13 128.09(12) . . ?
N6 C7 C8 104.50(12) . . ?
N6 C7 C12 131.70(13) . . ?
C8 C7 C12 123.72(13) . . ?
N4 C8 C7 106.57(11) . . ?
N4 C8 C9 132.80(13) . . ?
C7 C8 C9 120.60(13) . . ?
C8 C9 C19 124.65(13) . . ?
C10 C9 C8 115.01(13) . . ?
C10 C9 C19 120.32(13) . . ?
C9 C10 H10 118.3 . . ?
C9 C10 C11 123.44(14) . . ?
C11 C10 H10 118.3 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.90(14) . . ?
C12 C11 H11 119.1 . . ?
C7 C12 H12 122.4 . . ?
C11 C12 C7 115.27(13) . . ?
C11 C12 H12 122.4 . . ?
C14 C13 N6 119.20(12) . . ?
C18 C13 N6 118.58(12) . . ?
C18 C13 C14 122.21(12) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.32(12) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.54(12) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.09(12) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.10(13) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 118.73(12) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C20 C19 C9 173.18(15) . . ?
C19 C20 C21 178.57(16) . . ?
C22 C21 C20 121.74(13) . . ?
C22 C21 C26 119.22(13) . . ?
C26 C21 C20 119.04(13) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.58(14) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.78(15) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.02(14) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.79(14) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.61(14) . . ?
C25 C26 H26 119.7 . . ?

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
C2 B3 N4 N5 106.23(13) . . . . ?
C2 B3 N4 C8 -78.04(18) . . . . ?
B3 N4 N5 N6 176.48(11) . . . . ?
B3 N4 C8 C7 -174.96(13) . . . . ?
B3 N4 C8 C9 3.2(2) . . . . ?
N4 N5 N6 C7 -0.94(15) . . . . ?
N4 N5 N6 C13 -179.05(11) . . . . ?
N4 C8 C9 C10 -175.72(15) . . . . ?
N4 C8 C9 C19 5.8(2) . . . . ?
N5 N4 C8 C7 1.03(15) . . . . ?
N5 N4 C8 C9 179.22(14) . . . . ?
N5 N6 C7 C8 1.54(15) . . . . ?
N5 N6 C7 C12 -175.11(14) . . . . ?
N5 N6 C13 C14 47.97(18) . . . . ?
N5 N6 C13 C18 -133.44(14) . . . . ?
N6 C7 C8 N4 -1.51(14) . . . . ?
N6 C7 C8 C9 -179.97(12) . . . . ?
N6 C7 C12 C11 177.42(15) . . . . ?
N6 C13 C14 C15 178.36(12) . . . . ?
N6 C13 C18 C17 -178.20(13) . . . . ?
C7 N6 C13 C14 -129.80(15) . . . . ?
C7 N6 C13 C18 48.8(2) . . . . ?
C7 C8 C9 C10 2.3(2) . . . . ?
C7 C8 C9 C19 -176.19(13) . . . . ?
C8 N4 N5 N6 -0.09(14) . . . . ?
C8 C7 C12 C11 1.3(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C7 0.8(2) . . . . ?
C12 C7 C8 N4 175.48(13) . . . . ?
C12 C7 C8 C9 -3.0(2) . . . . ?
C13 N6 C7 C8 179.47(12) . . . . ?
C13 N6 C7 C12 2.8(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C14 C13 C18 C17 0.3(2) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C17 C18 C13 -0.2(2) . . . . ?
C18 C13 C14 C15 -0.2(2) . . . . ?
C19 C9 C10 C11 178.34(14) . . . . ?
C20 C21 C22 C23 -179.93(14) . . . . ?
C20 C21 C26 C25 -179.98(12) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C21 C26 C25 0.2(2) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 -0.5(2) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?
C26 C21 C22 C23 -0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_QT_167
_database_code_depnum_ccdc_archive 'CCDC 2113568'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 B N4, C H2 Cl2'
_chemical_formula_sum            'C22 H17 B Cl2 N4'
_chemical_formula_weight         419.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6707(2)
_cell_length_b                   8.6999(3)
_cell_length_c                   15.3408(5)
_cell_angle_alpha                95.9950(10)
_cell_angle_beta                 100.5720(10)
_cell_angle_gamma                91.4500(10)
_cell_volume                     999.84(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.61
_cell_measurement_theta_min      5.62
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.581
_exptl_absorpt_coefficient_mu    3.041
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0910 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.7930.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20096
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.024
_diffrn_reflns_theta_min         2.948
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3913
_reflns_number_total             4231
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.4426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0884
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.98104(15) 0.32688(15) 0.71340(8) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.85692(17) 0.36133(15) 0.66682(9) 0.0178(3) Uani 1 1 d . . . . .
B3 B 0.68320(19) 0.41285(17) 0.60422(10) 0.0170(3) Uani 1 1 d . . . . .
H3 H 0.713(2) 0.5343(18) 0.5882(10) 0.015(4) Uiso 1 1 d . . . . .
C4 C 0.50950(16) 0.40026(15) 0.65042(9) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.35907(16) 0.31537(15) 0.61205(9) 0.0174(3) Uani 1 1 d . . . . .
H5 H 0.260214 0.318736 0.641411 0.021 Uiso 1 1 calc R U . . .
C6 C 0.34456(16) 0.21932(15) 0.52729(9) 0.0167(2) Uani 1 1 d . . . . .
C7 C 0.49264(16) 0.21752(15) 0.48519(9) 0.0163(2) Uani 1 1 d . . . . .
N8 N 0.64789(13) 0.30120(12) 0.51455(7) 0.0158(2) Uani 1 1 d . . . . .
N9 N 0.75373(14) 0.28094(13) 0.45643(7) 0.0176(2) Uani 1 1 d . . . . .
N10 N 0.66554(14) 0.18255(13) 0.38858(7) 0.0165(2) Uani 1 1 d . . . . .
C11 C 0.49974(16) 0.13870(15) 0.40303(9) 0.0165(2) Uani 1 1 d . . . . .
C12 C 0.35204(17) 0.04784(15) 0.35471(9) 0.0189(3) Uani 1 1 d . . . . .
H12 H 0.353148 -0.008439 0.298321 0.023 Uiso 1 1 calc R U . . .
C13 C 0.20511(17) 0.04642(15) 0.39526(9) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.102302 -0.013531 0.365153 0.023 Uiso 1 1 calc R U . . .
C14 C 0.19944(17) 0.12958(15) 0.47938(9) 0.0188(3) Uani 1 1 d . . . . .
H14 H 0.094034 0.123621 0.503342 0.023 Uiso 1 1 calc R U . . .
C15 C 0.74376(16) 0.14833(16) 0.31103(8) 0.0174(3) Uani 1 1 d . . . . .
C16 C 0.84307(17) 0.26425(16) 0.28433(9) 0.0191(3) Uani 1 1 d . . . . .
H16 H 0.861437 0.363755 0.317393 0.023 Uiso 1 1 calc R U . . .
C17 C 0.91488(18) 0.23117(17) 0.20811(9) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.982843 0.308970 0.188509 0.026 Uiso 1 1 calc R U . . .
C18 C 0.88814(18) 0.08513(17) 0.16027(9) 0.0232(3) Uani 1 1 d . . . . .
H18 H 0.937641 0.063552 0.108142 0.028 Uiso 1 1 calc R U . . .
C19 C 0.78909(19) -0.02935(17) 0.18858(10) 0.0233(3) Uani 1 1 d . . . . .
H19 H 0.771198 -0.129055 0.155726 0.028 Uiso 1 1 calc R U . . .
C20 C 0.71598(18) 0.00132(16) 0.26479(9) 0.0206(3) Uani 1 1 d . . . . .
H20 H 0.648635 -0.076540 0.284701 0.025 Uiso 1 1 calc R U . . .
C21 C 0.51672(16) 0.49204(15) 0.73842(9) 0.0172(2) Uani 1 1 d . . . . .
C22 C 0.62728(17) 0.62622(15) 0.76331(9) 0.0193(3) Uani 1 1 d . . . . .
H22 H 0.701511 0.656260 0.724226 0.023 Uiso 1 1 calc R U . . .
C23 C 0.63043(18) 0.71608(16) 0.84397(10) 0.0233(3) Uani 1 1 d . . . . .
H23 H 0.704254 0.807904 0.858848 0.028 Uiso 1 1 calc R U . . .
C24 C 0.52583(19) 0.67208(18) 0.90303(10) 0.0254(3) Uani 1 1 d . . . . .
H24 H 0.527644 0.733463 0.958195 0.030 Uiso 1 1 calc R U . . .
C25 C 0.41870(18) 0.53741(18) 0.88049(9) 0.0243(3) Uani 1 1 d . . . . .
H25 H 0.348292 0.505839 0.920911 0.029 Uiso 1 1 calc R U . . .
C26 C 0.41372(17) 0.44876(16) 0.79950(9) 0.0205(3) Uani 1 1 d . . . . .
H26 H 0.339422 0.357182 0.785043 0.025 Uiso 1 1 calc R U . . .
C31 C 0.8338(2) 0.31170(18) 0.90534(10) 0.0276(3) Uani 1 1 d . . . . .
H31A H 0.773948 0.405284 0.924669 0.033 Uiso 1 1 calc R U . . .
H31B H 0.862098 0.323739 0.845931 0.033 Uiso 1 1 calc R U . . .
Cl32 Cl 0.68855(5) 0.14743(4) 0.89693(3) 0.03229(11) Uani 1 1 d . . . . .
Cl33 Cl 1.03312(4) 0.29562(4) 0.98225(2) 0.02709(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.1473(18) . ?
C2 B3 1.5968(19) . ?
B3 H3 1.137(16) . ?
B3 C4 1.6263(18) . ?
B3 N8 1.5748(18) . ?
C4 C5 1.3566(18) . ?
C4 C21 1.4861(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4548(19) . ?
C6 C7 1.4055(17) . ?
C6 C14 1.3874(18) . ?
C7 N8 1.3572(16) . ?
C7 C11 1.3815(19) . ?
N8 N9 1.3134(15) . ?
N9 N10 1.3416(16) . ?
N10 C11 1.3816(16) . ?
N10 C15 1.4356(16) . ?
C11 C12 1.4078(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3841(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.421(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3881(18) . ?
C15 C20 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3883(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.4020(18) . ?
C21 C26 1.4051(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(2) . ?
C26 H26 0.9500 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 Cl32 1.7689(15) . ?
C31 Cl33 1.7698(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 B3 178.37(14) . . ?
C2 B3 H3 107.1(8) . . ?
C2 B3 C4 111.49(10) . . ?
C4 B3 H3 113.3(8) . . ?
N8 B3 C2 108.55(11) . . ?
N8 B3 H3 108.4(8) . . ?
N8 B3 C4 107.87(10) . . ?
C5 C4 B3 123.80(12) . . ?
C5 C4 C21 119.05(11) . . ?
C21 C4 B3 117.12(11) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.99(12) . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 117.67(11) . . ?
C14 C6 C5 128.46(12) . . ?
C14 C6 C7 113.84(12) . . ?
N8 C7 C6 126.22(12) . . ?
N8 C7 C11 108.13(11) . . ?
C11 C7 C6 125.49(12) . . ?
C7 N8 B3 122.29(10) . . ?
N9 N8 B3 126.88(10) . . ?
N9 N8 C7 110.74(11) . . ?
N8 N9 N10 106.14(10) . . ?
N9 N10 C11 111.69(10) . . ?
N9 N10 C15 118.65(10) . . ?
C11 N10 C15 129.42(11) . . ?
C7 C11 N10 103.31(11) . . ?
C7 C11 C12 120.41(12) . . ?
N10 C11 C12 136.19(12) . . ?
C11 C12 H12 122.4 . . ?
C13 C12 C11 115.18(12) . . ?
C13 C12 H12 122.4 . . ?
C12 C13 H13 118.2 . . ?
C12 C13 C14 123.67(12) . . ?
C14 C13 H13 118.2 . . ?
C6 C14 C13 121.41(12) . . ?
C6 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 N10 118.75(12) . . ?
C20 C15 N10 118.98(11) . . ?
C20 C15 C16 122.26(12) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.36(13) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.52(13) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.09(13) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.33(13) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 118.43(12) . . ?
C15 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C22 C21 C4 120.75(12) . . ?
C22 C21 C26 117.51(12) . . ?
C26 C21 C4 121.73(12) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.31(12) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.21(13) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.30(13) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.52(13) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 H26 119.4 . . ?
C25 C26 C21 121.12(13) . . ?
C25 C26 H26 119.4 . . ?
H31A C31 H31B 108.0 . . ?
Cl32 C31 H31A 109.3 . . ?
Cl32 C31 H31B 109.3 . . ?
Cl32 C31 Cl33 111.61(8) . . ?
Cl33 C31 H31A 109.3 . . ?
Cl33 C31 H31B 109.3 . . ?

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
C2 B3 C4 C5 -123.52(13) . . . . ?
C2 B3 C4 C21 58.53(15) . . . . ?
C2 B3 N8 C7 122.84(12) . . . . ?
C2 B3 N8 N9 -61.01(15) . . . . ?
B3 C4 C5 C6 3.91(19) . . . . ?
B3 C4 C21 C22 25.36(17) . . . . ?
B3 C4 C21 C26 -154.83(12) . . . . ?
B3 N8 N9 N10 -176.59(11) . . . . ?
C4 B3 N8 C7 1.90(16) . . . . ?
C4 B3 N8 N9 178.05(11) . . . . ?
C4 C5 C6 C7 -0.41(18) . . . . ?
C4 C5 C6 C14 -178.47(13) . . . . ?
C4 C21 C22 C23 177.63(12) . . . . ?
C4 C21 C26 C25 -178.49(12) . . . . ?
C5 C4 C21 C22 -152.70(12) . . . . ?
C5 C4 C21 C26 27.11(18) . . . . ?
C5 C6 C7 N8 -2.28(19) . . . . ?
C5 C6 C7 C11 -177.02(12) . . . . ?
C5 C6 C14 C13 177.58(12) . . . . ?
C6 C7 N8 B3 1.22(19) . . . . ?
C6 C7 N8 N9 -175.49(12) . . . . ?
C6 C7 C11 N10 175.60(12) . . . . ?
C6 C7 C11 C12 -1.4(2) . . . . ?
C7 C6 C14 C13 -0.55(18) . . . . ?
C7 N8 N9 N10 -0.07(13) . . . . ?
C7 C11 C12 C13 0.58(18) . . . . ?
N8 B3 C4 C5 -4.43(17) . . . . ?
N8 B3 C4 C21 177.62(10) . . . . ?
N8 C7 C11 N10 0.06(13) . . . . ?
N8 C7 C11 C12 -176.93(11) . . . . ?
N8 N9 N10 C11 0.11(14) . . . . ?
N8 N9 N10 C15 175.02(10) . . . . ?
N9 N10 C11 C7 -0.10(14) . . . . ?
N9 N10 C11 C12 176.14(14) . . . . ?
N9 N10 C15 C16 -34.55(17) . . . . ?
N9 N10 C15 C20 146.16(12) . . . . ?
N10 C11 C12 C13 -175.18(14) . . . . ?
N10 C15 C16 C17 -178.57(11) . . . . ?
N10 C15 C20 C19 178.55(12) . . . . ?
C11 C7 N8 B3 176.72(11) . . . . ?
C11 C7 N8 N9 0.01(14) . . . . ?
C11 N10 C15 C16 139.32(13) . . . . ?
C11 N10 C15 C20 -39.97(19) . . . . ?
C11 C12 C13 C14 0.13(19) . . . . ?
C12 C13 C14 C6 -0.1(2) . . . . ?
C14 C6 C7 N8 176.06(12) . . . . ?
C14 C6 C7 C11 1.32(19) . . . . ?
C15 N10 C11 C7 -174.32(12) . . . . ?
C15 N10 C11 C12 1.9(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C15 C20 C19 -0.7(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C15 0.3(2) . . . . ?
C20 C15 C16 C17 0.69(19) . . . . ?
C21 C4 C5 C6 -178.17(11) . . . . ?
C21 C22 C23 C24 1.5(2) . . . . ?
C22 C21 C26 C25 1.33(19) . . . . ?
C22 C23 C24 C25 0.1(2) . . . . ?
C23 C24 C25 C26 -1.0(2) . . . . ?
C24 C25 C26 C21 0.2(2) . . . . ?
C26 C21 C22 C23 -2.19(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_n3_r3
_database_code_depnum_ccdc_archive 'CCDC 2113566'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 B N4 O'
_chemical_formula_sum            'C22 H17 B N4 O'
_chemical_formula_weight         364.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.69490(10)
_cell_length_b                   9.99890(10)
_cell_length_c                   10.3454(2)
_cell_angle_alpha                74.2200(8)
_cell_angle_beta                 68.3124(6)
_cell_angle_gamma                89.2819(7)
_cell_volume                     892.41(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9524
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.825
_cell_measurement_theta_min      4.618
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0785 before and 0.0538 after correction. The Ratio of minimum to maximum transmission is 0.9427. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20032
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.035
_diffrn_reflns_theta_min         4.618
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3214
_reflns_number_total             3786
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.4210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1014
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.53465(15) 0.10474(14) 0.27284(14) 0.0291(3) Uani 1 1 d . . . . .
C2 C 0.52523(14) 0.17903(14) 0.34146(14) 0.0206(3) Uani 1 1 d . . . . .
B3 B 0.51550(16) 0.29244(16) 0.42724(16) 0.0190(3) Uani 1 1 d . . . . .
H3 H 0.6009(18) 0.3844(17) 0.3546(17) 0.023(4) Uiso 1 1 d . . . . .
C4 C 0.34830(14) 0.33993(13) 0.48836(14) 0.0188(3) Uani 1 1 d . . . . .
C5 C 0.27349(14) 0.33912(14) 0.62798(14) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.177819 0.372707 0.654329 0.023 Uiso 1 1 calc R . . . .
C6 C 0.33520(14) 0.28836(13) 0.73882(14) 0.0180(3) Uani 1 1 d . . . . .
C7 C 0.47517(14) 0.23590(13) 0.69659(14) 0.0170(3) Uani 1 1 d . . . . .
N8 N 0.56100(12) 0.22929(11) 0.56120(12) 0.0177(2) Uani 1 1 d . . . . .
N9 N 0.68584(12) 0.17574(12) 0.55961(12) 0.0188(2) Uani 1 1 d . . . . .
N10 N 0.67991(12) 0.14658(11) 0.69632(11) 0.0177(2) Uani 1 1 d . . . . .
C11 C 0.55011(14) 0.18254(13) 0.78717(14) 0.0171(3) Uani 1 1 d . . . . .
C12 C 0.48705(14) 0.17633(13) 0.93563(14) 0.0183(3) Uani 1 1 d . . . . .
H12 H 0.535008 0.138821 1.000887 0.022 Uiso 1 1 calc R . . . .
C13 C 0.35037(15) 0.22891(14) 0.97876(14) 0.0200(3) Uani 1 1 d . . . . .
H13 H 0.303925 0.228439 1.077431 0.024 Uiso 1 1 calc R . . . .
C14 C 0.27506(14) 0.28377(13) 0.88395(14) 0.0187(3) Uani 1 1 d . . . . .
H14 H 0.181017 0.318137 0.921270 0.022 Uiso 1 1 calc R . . . .
C15 C 0.80352(14) 0.08920(14) 0.72760(13) 0.0174(3) Uani 1 1 d . . . . .
C16 C 0.86980(15) -0.01701(14) 0.67104(14) 0.0214(3) Uani 1 1 d . . . . .
H16 H 0.830441 -0.055972 0.616239 0.026 Uiso 1 1 calc R . . . .
C17 C 0.99566(15) -0.06512(15) 0.69669(15) 0.0248(3) Uani 1 1 d . . . . .
H17 H 1.043933 -0.136515 0.657407 0.030 Uiso 1 1 calc R . . . .
C18 C 1.05065(15) -0.00985(15) 0.77867(15) 0.0244(3) Uani 1 1 d . . . . .
H18 H 1.137477 -0.042154 0.794064 0.029 Uiso 1 1 calc R . . . .
C19 C 0.97932(16) 0.09304(15) 0.83885(16) 0.0249(3) Uani 1 1 d . . . . .
H19 H 1.015378 0.128463 0.898069 0.030 Uiso 1 1 calc R . . . .
C20 C 0.85575(15) 0.14383(14) 0.81243(15) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.807479 0.215105 0.851918 0.025 Uiso 1 1 calc R . . . .
C21 C 0.27784(14) 0.39187(13) 0.38123(14) 0.0185(3) Uani 1 1 d . . . . .
C22 C 0.36319(14) 0.46513(14) 0.23732(14) 0.0192(3) Uani 1 1 d . . . . .
H22 H 0.468531 0.477614 0.207153 0.023 Uiso 1 1 calc R . . . .
C23 C 0.29885(14) 0.52051(14) 0.13654(14) 0.0194(3) Uani 1 1 d . . . . .
H23 H 0.359728 0.570212 0.039412 0.023 Uiso 1 1 calc R . . . .
C24 C 0.14463(14) 0.50245(13) 0.17928(14) 0.0185(3) Uani 1 1 d . . . . .
C25 C 0.05712(15) 0.42491(14) 0.32094(15) 0.0211(3) Uani 1 1 d . . . . .
H25 H -0.047759 0.409198 0.349510 0.025 Uiso 1 1 calc R . . . .
C26 C 0.12261(15) 0.37091(14) 0.41981(15) 0.0210(3) Uani 1 1 d . . . . .
H26 H 0.061608 0.318496 0.515897 0.025 Uiso 1 1 calc R . . . .
O27 O 0.06928(10) 0.55808(10) 0.09118(10) 0.0232(2) Uani 1 1 d . . . . .
C28 C 0.15679(16) 0.63575(15) -0.05532(15) 0.0238(3) Uani 1 1 d . . . . .
H28A H 0.090709 0.670936 -0.106648 0.036 Uiso 1 1 calc GR . . . .
H28B H 0.223640 0.575008 -0.104281 0.036 Uiso 1 1 calc GR . . . .
H28C H 0.215975 0.714533 -0.055391 0.036 Uiso 1 1 calc GR . . . .


_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 C2 1.1407(18) . ?
C2 B3 1.602(2) . ?
B3 H3 1.131(16) . ?
B3 C4 1.6246(19) . ?
B3 N8 1.5756(18) . ?
C4 C5 1.3535(18) . ?
C4 C21 1.4841(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4537(18) . ?
C6 C7 1.4057(17) . ?
C6 C14 1.3829(18) . ?
C7 N8 1.3588(16) . ?
C7 C11 1.3829(18) . ?
N8 N9 1.3136(15) . ?
N9 N10 1.3433(15) . ?
N10 C11 1.3764(16) . ?
N10 C15 1.4277(16) . ?
C11 C12 1.4113(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3801(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.4222(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3878(18) . ?
C15 C20 1.3861(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3950(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.3852(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.3962(18) . ?
C21 C26 1.4094(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3931(18) . ?
C23 H23 0.9500 . ?
C23 C24 1.3922(18) . ?
C24 C25 1.3957(19) . ?
C24 O27 1.3711(15) . ?
C25 H25 0.9500 . ?
C25 C26 1.3828(19) . ?
C26 H26 0.9500 . ?
O27 C28 1.4304(16) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 B3 175.87(14) . . ?
C2 B3 H3 109.2(8) . . ?
C2 B3 C4 112.24(11) . . ?
C4 B3 H3 112.0(8) . . ?
N8 B3 C2 109.70(11) . . ?
N8 B3 H3 105.7(8) . . ?
N8 B3 C4 107.74(10) . . ?
C5 C4 B3 124.06(12) . . ?
C5 C4 C21 119.05(12) . . ?
C21 C4 B3 116.85(11) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.95(12) . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 117.38(11) . . ?
C14 C6 C5 128.91(12) . . ?
C14 C6 C7 113.72(12) . . ?
N8 C7 C6 126.65(12) . . ?
N8 C7 C11 107.99(11) . . ?
C11 C7 C6 125.36(12) . . ?
C7 N8 B3 121.73(10) . . ?
N9 N8 B3 127.32(10) . . ?
N9 N8 C7 110.72(11) . . ?
N8 N9 N10 106.04(10) . . ?
N9 N10 C11 111.82(10) . . ?
N9 N10 C15 118.84(10) . . ?
C11 N10 C15 129.31(11) . . ?
C7 C11 C12 120.61(12) . . ?
N10 C11 C7 103.42(11) . . ?
N10 C11 C12 135.97(12) . . ?
C11 C12 H12 122.6 . . ?
C13 C12 C11 114.86(12) . . ?
C13 C12 H12 122.6 . . ?
C12 C13 H13 118.1 . . ?
C12 C13 C14 123.76(12) . . ?
C14 C13 H13 118.1 . . ?
C6 C14 C13 121.69(12) . . ?
C6 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C16 C15 N10 119.81(11) . . ?
C20 C15 N10 118.44(11) . . ?
C20 C15 C16 121.74(12) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.33(13) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.54(13) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.21(13) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.03(13) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.5 . . ?
C19 C20 C15 119.08(13) . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C4 121.10(12) . . ?
C22 C21 C26 117.04(12) . . ?
C26 C21 C4 121.86(12) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 C21 122.12(12) . . ?
C23 C22 H22 118.9 . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.48(12) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 119.59(12) . . ?
O27 C24 C23 124.30(12) . . ?
O27 C24 C25 116.10(11) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.20(12) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.3 . . ?
C25 C26 C21 121.48(12) . . ?
C25 C26 H26 119.3 . . ?
C24 O27 C28 117.12(10) . . ?
O27 C28 H28A 109.5 . . ?
O27 C28 H28B 109.5 . . ?
O27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 B3 C4 C5 128.14(13) . . . . ?
C2 B3 C4 C21 -54.18(15) . . . . ?
C2 B3 N8 C7 -130.21(12) . . . . ?
C2 B3 N8 N9 55.83(16) . . . . ?
B3 C4 C5 C6 -3.0(2) . . . . ?
B3 C4 C21 C22 -32.89(17) . . . . ?
B3 C4 C21 C26 147.69(12) . . . . ?
B3 N8 N9 N10 174.90(11) . . . . ?
C4 B3 N8 C7 -7.76(16) . . . . ?
C4 B3 N8 N9 178.28(11) . . . . ?
C4 C5 C6 C7 -1.72(19) . . . . ?
C4 C5 C6 C14 178.30(13) . . . . ?
C4 C21 C22 C23 -176.94(12) . . . . ?
C4 C21 C26 C25 177.13(12) . . . . ?
C5 C4 C21 C22 144.92(13) . . . . ?
C5 C4 C21 C26 -34.50(18) . . . . ?
C5 C6 C7 N8 1.03(19) . . . . ?
C5 C6 C7 C11 -179.49(12) . . . . ?
C5 C6 C14 C13 179.34(12) . . . . ?
C6 C7 N8 B3 4.44(19) . . . . ?
C6 C7 N8 N9 179.31(12) . . . . ?
C6 C7 C11 N10 -179.56(12) . . . . ?
C6 C7 C11 C12 0.4(2) . . . . ?
C7 C6 C14 C13 -0.64(18) . . . . ?
C7 N8 N9 N10 0.39(14) . . . . ?
C7 C11 C12 C13 -1.09(18) . . . . ?
N8 B3 C4 C5 7.26(17) . . . . ?
N8 B3 C4 C21 -175.05(10) . . . . ?
N8 C7 C11 N10 0.00(13) . . . . ?
N8 C7 C11 C12 179.96(11) . . . . ?
N8 N9 N10 C11 -0.40(14) . . . . ?
N8 N9 N10 C15 -178.66(10) . . . . ?
N9 N10 C11 C7 0.24(14) . . . . ?
N9 N10 C11 C12 -179.71(14) . . . . ?
N9 N10 C15 C16 -44.12(17) . . . . ?
N9 N10 C15 C20 134.74(13) . . . . ?
N10 C11 C12 C13 178.86(14) . . . . ?
N10 C15 C16 C17 176.33(12) . . . . ?
N10 C15 C20 C19 -177.44(12) . . . . ?
C11 C7 N8 B3 -175.11(11) . . . . ?
C11 C7 N8 N9 -0.25(14) . . . . ?
C11 N10 C15 C16 137.97(14) . . . . ?
C11 N10 C15 C20 -43.18(19) . . . . ?
C11 C12 C13 C14 0.96(19) . . . . ?
C12 C13 C14 C6 -0.1(2) . . . . ?
C14 C6 C7 N8 -178.99(12) . . . . ?
C14 C6 C7 C11 0.49(19) . . . . ?
C15 N10 C11 C7 178.28(12) . . . . ?
C15 N10 C11 C12 -1.7(2) . . . . ?
C15 C16 C17 C18 1.2(2) . . . . ?
C16 C15 C20 C19 1.4(2) . . . . ?
C16 C17 C18 C19 1.1(2) . . . . ?
C17 C18 C19 C20 -2.2(2) . . . . ?
C18 C19 C20 C15 1.0(2) . . . . ?
C20 C15 C16 C17 -2.5(2) . . . . ?
C21 C4 C5 C6 179.36(11) . . . . ?
C21 C22 C23 C24 -0.24(19) . . . . ?
C22 C21 C26 C25 -2.32(19) . . . . ?
C22 C23 C24 C25 -2.29(19) . . . . ?
C22 C23 C24 O27 176.75(12) . . . . ?
C23 C24 C25 C26 2.47(19) . . . . ?
C23 C24 O27 C28 2.09(18) . . . . ?
C24 C25 C26 C21 -0.1(2) . . . . ?
C25 C24 O27 C28 -178.85(11) . . . . ?
C26 C21 C22 C23 2.50(19) . . . . ?
O27 C24 C25 C26 -176.64(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_N3_76
_database_code_depnum_ccdc_archive 'CCDC 2113565'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 B N4'
_chemical_formula_sum            'C15 H11 B N4'
_chemical_formula_weight         258.09
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.4138(4)
_cell_length_b                   5.27510(10)
_cell_length_c                   15.4456(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1255.87(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8947
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.94
_cell_measurement_theta_min      5.73
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.8875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1311 before and 0.0907 after correction.
The Ratio of minimum to maximum transmission is 0.8976.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23198
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.739
_diffrn_reflns_theta_min         5.729
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                2412
_reflns_number_total             2636
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2636
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.4136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0946
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.66263(17) 0.1694(5) 0.25345(19) 0.0301(6) Uani 1 1 d . . . . .
H3 H 0.677(2) -0.257(6) 0.413(2) 0.017(8) Uiso 1 1 d . . . . .
C2 C 0.64370(19) 0.0389(5) 0.3107(2) 0.0255(6) Uani 1 1 d . . . . .
B3 B 0.6147(2) -0.1415(6) 0.3883(2) 0.0227(7) Uani 1 1 d . . . . .
C4 C 0.5379(2) -0.3298(5) 0.35878(19) 0.0215(6) Uani 1 1 d . . . . .
H4 H 0.552642 -0.458628 0.318408 0.026 Uiso 1 1 calc R . . . .
C5 C 0.4550(2) -0.3224(5) 0.3856(2) 0.0238(6) Uani 1 1 d . . . . .
H5 H 0.414683 -0.442127 0.363518 0.029 Uiso 1 1 calc R . . . .
C6 C 0.42592(18) -0.1329(5) 0.44839(18) 0.0193(6) Uani 1 1 d . . . . .
C7 C 0.48940(17) 0.0348(5) 0.48113(17) 0.0174(5) Uani 1 1 d . . . . .
N8 N 0.57519(15) 0.0355(4) 0.46099(15) 0.0190(5) Uani 1 1 d . . . . .
N9 N 0.61686(14) 0.2020(4) 0.50891(16) 0.0199(5) Uani 1 1 d . . . . .
N10 N 0.55749(14) 0.3108(4) 0.56027(16) 0.0182(5) Uani 1 1 d . . . . .
C11 C 0.47539(16) 0.2137(5) 0.54511(19) 0.0179(5) Uani 1 1 d . . . . .
C12 C 0.39210(18) 0.2458(5) 0.58108(19) 0.0215(6) Uani 1 1 d . . . . .
H12 H 0.380389 0.367124 0.624991 0.026 Uiso 1 1 calc R . . . .
C13 C 0.32858(18) 0.0879(6) 0.5479(2) 0.0253(6) Uani 1 1 d . . . . .
H13 H 0.271147 0.105197 0.569415 0.030 Uiso 1 1 calc R . . . .
C14 C 0.34440(18) -0.0984(5) 0.48360(19) 0.0232(6) Uani 1 1 d . . . . .
H14 H 0.297814 -0.201877 0.464276 0.028 Uiso 1 1 calc R . . . .
C15 C 0.58615(18) 0.4894(5) 0.62405(17) 0.0174(5) Uani 1 1 d . . . . .
C16 C 0.66837(18) 0.4609(5) 0.65927(19) 0.0195(5) Uani 1 1 d . . . . .
H16 H 0.704628 0.324350 0.642002 0.023 Uiso 1 1 calc R . . . .
C17 C 0.69666(18) 0.6356(5) 0.7202(2) 0.0220(6) Uani 1 1 d . . . . .
H17 H 0.752944 0.619639 0.744630 0.026 Uiso 1 1 calc R . . . .
C18 C 0.64278(18) 0.8345(5) 0.74561(18) 0.0215(6) Uani 1 1 d . . . . .
H18 H 0.662728 0.955433 0.786596 0.026 Uiso 1 1 calc R . . . .
C19 C 0.56030(18) 0.8554(5) 0.71112(19) 0.0210(6) Uani 1 1 d . . . . .
H19 H 0.523356 0.988871 0.729732 0.025 Uiso 1 1 calc R . . . .
C20 C 0.53071(18) 0.6833(5) 0.64939(19) 0.0199(6) Uani 1 1 d . . . . .
H20 H 0.474218 0.698066 0.625330 0.024 Uiso 1 1 calc R . . . .


_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 C2 1.158(4) . ?
C2 B3 1.594(5) . ?
B3 H3 1.20(3) . ?
B3 C4 1.612(4) . ?
B3 N8 1.582(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.344(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.463(4) . ?
C6 C7 1.413(4) . ?
C6 C14 1.381(4) . ?
C7 N8 1.358(4) . ?
C7 C11 1.383(4) . ?
N8 N9 1.316(3) . ?
N9 N10 1.340(3) . ?
N10 C11 1.385(3) . ?
N10 C15 1.433(3) . ?
C11 C12 1.409(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.418(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(4) . ?
C15 C20 1.389(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(4) . ?
C20 H20 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
N1 C2 B3 178.3(3) . . ?
C2 B3 H3 108.8(16) . . ?
C2 B3 C4 111.1(2) . . ?
C4 B3 H3 111.4(15) . . ?
N8 B3 H3 112.3(16) . . ?
N8 B3 C2 106.8(2) . . ?
N8 B3 C4 106.3(2) . . ?
B3 C4 H4 116.8 . . ?
C5 C4 B3 126.4(3) . . ?
C5 C4 H4 116.8 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 116.9(3) . . ?
C14 C6 C5 129.1(3) . . ?
C14 C6 C7 114.0(3) . . ?
N8 C7 C6 126.4(2) . . ?
N8 C7 C11 108.3(2) . . ?
C11 C7 C6 125.1(2) . . ?
C7 N8 B3 122.4(2) . . ?
N9 N8 B3 127.2(2) . . ?
N9 N8 C7 110.4(2) . . ?
N8 N9 N10 106.6(2) . . ?
N9 N10 C11 111.4(2) . . ?
N9 N10 C15 118.5(2) . . ?
C11 N10 C15 129.9(2) . . ?
C7 C11 N10 103.3(2) . . ?
C7 C11 C12 120.4(2) . . ?
N10 C11 C12 136.2(3) . . ?
C11 C12 H12 122.4 . . ?
C13 C12 C11 115.2(3) . . ?
C13 C12 H12 122.4 . . ?
C12 C13 H13 118.2 . . ?
C12 C13 C14 123.7(3) . . ?
C14 C13 H13 118.2 . . ?
C6 C14 C13 121.6(3) . . ?
C6 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C16 C15 N10 118.7(2) . . ?
C16 C15 C20 122.1(2) . . ?
C20 C15 N10 119.2(2) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 118.1(3) . . ?
C15 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?

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
C2 B3 C4 C5 -110.8(3) . . . . ?
C2 B3 N8 C7 111.1(3) . . . . ?
C2 B3 N8 N9 -67.9(3) . . . . ?
B3 C4 C5 C6 -0.6(5) . . . . ?
B3 N8 N9 N10 178.9(2) . . . . ?
C4 B3 N8 C7 -7.6(3) . . . . ?
C4 B3 N8 N9 173.3(2) . . . . ?
C4 C5 C6 C7 -2.0(4) . . . . ?
C4 C5 C6 C14 -179.4(3) . . . . ?
C5 C6 C7 N8 -1.0(4) . . . . ?
C5 C6 C7 C11 -175.2(3) . . . . ?
C5 C6 C14 C13 176.4(3) . . . . ?
C6 C7 N8 B3 6.4(4) . . . . ?
C6 C7 N8 N9 -174.4(3) . . . . ?
C6 C7 C11 N10 174.3(2) . . . . ?
C6 C7 C11 C12 -2.1(4) . . . . ?
C7 C6 C14 C13 -1.1(4) . . . . ?
C7 N8 N9 N10 -0.3(3) . . . . ?
C7 C11 C12 C13 0.1(4) . . . . ?
N8 B3 C4 C5 5.0(4) . . . . ?
N8 C7 C11 N10 -0.8(3) . . . . ?
N8 C7 C11 C12 -177.3(2) . . . . ?
N8 N9 N10 C11 -0.3(3) . . . . ?
N8 N9 N10 C15 175.8(2) . . . . ?
N9 N10 C11 C7 0.7(3) . . . . ?
N9 N10 C11 C12 176.3(3) . . . . ?
N9 N10 C15 C16 -30.0(4) . . . . ?
N9 N10 C15 C20 150.8(2) . . . . ?
N10 C11 C12 C13 -174.9(3) . . . . ?
N10 C15 C16 C17 179.2(3) . . . . ?
N10 C15 C20 C19 -179.6(2) . . . . ?
C11 C7 N8 B3 -178.5(2) . . . . ?
C11 C7 N8 N9 0.7(3) . . . . ?
C11 N10 C15 C16 145.2(3) . . . . ?
C11 N10 C15 C20 -34.0(4) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C12 C13 C14 C6 -0.8(5) . . . . ?
C14 C6 C7 N8 176.8(3) . . . . ?
C14 C6 C7 C11 2.5(4) . . . . ?
C15 N10 C11 C7 -174.8(3) . . . . ?
C15 N10 C11 C12 0.8(5) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C15 C20 C19 1.1(4) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
C17 C18 C19 C20 -1.5(4) . . . . ?
C18 C19 C20 C15 0.4(4) . . . . ?
C20 C15 C16 C17 -1.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_QT_131
_database_code_depnum_ccdc_archive 'CCDC 2113567'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 B N4'
_chemical_formula_sum            'C22 H17 B N4'
_chemical_formula_weight         348.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.1974(2)
_cell_length_b                   14.8004(5)
_cell_length_c                   16.7357(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.3030(10)
_cell_angle_gamma                90
_cell_volume                     1754.01(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.80
_cell_measurement_theta_min      4.02
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1371 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.8021.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29054
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.143
_diffrn_reflns_theta_min         4.016
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3606
_reflns_number_total             3773
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+0.7462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1133
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.45293(15) 0.78235(8) 0.70413(6) 0.0239(2) Uani 1 1 d . . . . .
C2 C 0.44962(15) 0.81370(8) 0.64116(7) 0.0168(2) Uani 1 1 d . . . . .
B3 B 0.44070(17) 0.85887(8) 0.55371(7) 0.0146(2) Uani 1 1 d . . . . .
H3 H 0.3351(19) 0.9176(10) 0.5477(8) 0.018(3) Uiso 1 1 d . . . . .
C4 C 0.64787(15) 0.88980(7) 0.53786(6) 0.0138(2) Uani 1 1 d . . . . .
C5 C 0.71980(15) 0.86616(7) 0.47136(6) 0.0146(2) Uani 1 1 d . . . . .
H5 H 0.837850 0.890544 0.464241 0.018 Uiso 1 1 calc R U . . .
C6 C 0.62104(15) 0.80439(7) 0.41052(6) 0.0144(2) Uani 1 1 d . . . . .
C7 C 0.44974(15) 0.76758(7) 0.42438(6) 0.0139(2) Uani 1 1 d . . . . .
N8 N 0.36182(12) 0.78597(6) 0.48780(6) 0.0142(2) Uani 1 1 d . . . . .
N9 N 0.20593(13) 0.73809(7) 0.48273(6) 0.0164(2) Uani 1 1 d . . . . .
N10 N 0.19388(13) 0.68820(6) 0.41536(6) 0.0157(2) Uani 1 1 d . . . . .
C11 C 0.34146(15) 0.70433(7) 0.37562(7) 0.0153(2) Uani 1 1 d . . . . .
C12 C 0.39782(16) 0.67228(8) 0.30435(7) 0.0171(2) Uani 1 1 d . . . . .
H12 H 0.327264 0.628721 0.269826 0.021 Uiso 1 1 calc R U . . .
C13 C 0.56371(16) 0.70923(8) 0.28871(7) 0.0182(2) Uani 1 1 d . . . . .
H13 H 0.606913 0.690558 0.240889 0.022 Uiso 1 1 calc R U . . .
C14 C 0.67405(15) 0.77359(8) 0.33980(7) 0.0168(2) Uani 1 1 d . . . . .
H14 H 0.786882 0.795960 0.324995 0.020 Uiso 1 1 calc R U . . .
C15 C 0.03297(15) 0.62713(8) 0.39323(7) 0.0182(2) Uani 1 1 d . . . . .
H15A H -0.030731 0.641378 0.337202 0.022 Uiso 1 1 calc R U . . .
H15B H -0.058398 0.638724 0.429787 0.022 Uiso 1 1 calc R U . . .
C16 C 0.08366(16) 0.52777(8) 0.39760(6) 0.0171(2) Uani 1 1 d . . . . .
C17 C 0.26389(17) 0.49403(8) 0.42439(7) 0.0229(3) Uani 1 1 d . . . . .
H17 H 0.365562 0.534330 0.442285 0.027 Uiso 1 1 calc R U . . .
C18 C 0.29623(19) 0.40091(9) 0.42512(8) 0.0275(3) Uani 1 1 d . . . . .
H18 H 0.420109 0.378232 0.443152 0.033 Uiso 1 1 calc R U . . .
C19 C 0.1490(2) 0.34150(9) 0.39976(8) 0.0274(3) Uani 1 1 d . . . . .
H19 H 0.171569 0.278245 0.400329 0.033 Uiso 1 1 calc R U . . .
C20 C -0.03189(19) 0.37488(9) 0.37347(8) 0.0260(3) Uani 1 1 d . . . . .
H20 H -0.133544 0.334319 0.356388 0.031 Uiso 1 1 calc R U . . .
C21 C -0.06466(17) 0.46739(8) 0.37206(7) 0.0214(3) Uani 1 1 d . . . . .
H21 H -0.188590 0.489821 0.353635 0.026 Uiso 1 1 calc R U . . .
C22 C 0.75973(15) 0.94937(7) 0.59996(6) 0.0146(2) Uani 1 1 d . . . . .
C23 C 0.66954(16) 1.00894(8) 0.64597(7) 0.0172(2) Uani 1 1 d . . . . .
H23 H 0.535498 1.010985 0.637093 0.021 Uiso 1 1 calc R U . . .
C24 C 0.77265(17) 1.06496(8) 0.70426(7) 0.0203(2) Uani 1 1 d . . . . .
H24 H 0.708975 1.105511 0.734151 0.024 Uiso 1 1 calc R U . . .
C25 C 0.96919(17) 1.06175(8) 0.71893(7) 0.0213(3) Uani 1 1 d . . . . .
H25 H 1.039965 1.099833 0.758886 0.026 Uiso 1 1 calc R U . . .
C26 C 1.06118(16) 1.00232(8) 0.67462(7) 0.0212(3) Uani 1 1 d . . . . .
H26 H 1.195222 0.999737 0.684534 0.025 Uiso 1 1 calc R U . . .
C27 C 0.95783(16) 0.94668(8) 0.61588(7) 0.0179(2) Uani 1 1 d . . . . .
H27 H 1.022269 0.906309 0.586143 0.022 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 C2 1.1478(16) . ?
C2 B3 1.5999(16) . ?
B3 H3 1.147(14) . ?
B3 C4 1.6263(15) . ?
B3 N8 1.5746(15) . ?
C4 C5 1.3546(15) . ?
C4 C22 1.4855(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.4556(15) . ?
C6 C7 1.4047(15) . ?
C6 C14 1.3841(15) . ?
C7 N8 1.3568(13) . ?
C7 C11 1.3864(15) . ?
N8 N9 1.3169(13) . ?
N9 N10 1.3375(13) . ?
N10 C11 1.3713(14) . ?
N10 C15 1.4635(14) . ?
C11 C12 1.4089(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3802(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.4236(16) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5137(16) . ?
C16 C17 1.3875(16) . ?
C16 C21 1.3992(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3974(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3840(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.3889(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.4036(15) . ?
C22 C27 1.4034(15) . ?
C23 H23 0.9500 . ?
C23 C24 1.3896(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.3926(17) . ?
C25 H25 0.9500 . ?
C25 C26 1.3919(18) . ?
C26 H26 0.9500 . ?
C26 C27 1.3915(16) . ?
C27 H27 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
N1 C2 B3 178.60(12) . . ?
C2 B3 H3 108.3(7) . . ?
C2 B3 C4 112.27(9) . . ?
C4 B3 H3 112.6(7) . . ?
N8 B3 C2 107.75(9) . . ?
N8 B3 H3 107.9(7) . . ?
N8 B3 C4 107.75(8) . . ?
C5 C4 B3 123.89(10) . . ?
C5 C4 C22 119.29(9) . . ?
C22 C4 B3 116.80(9) . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.75(10) . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 117.48(9) . . ?
C14 C6 C5 129.06(10) . . ?
C14 C6 C7 113.44(10) . . ?
N8 C7 C6 126.68(10) . . ?
N8 C7 C11 107.71(9) . . ?
C11 C7 C6 125.61(10) . . ?
C7 N8 B3 121.68(9) . . ?
N9 N8 B3 127.60(9) . . ?
N9 N8 C7 110.66(9) . . ?
N8 N9 N10 106.11(8) . . ?
N9 N10 C11 111.94(9) . . ?
N9 N10 C15 118.91(9) . . ?
C11 N10 C15 129.15(10) . . ?
C7 C11 C12 120.60(10) . . ?
N10 C11 C7 103.57(9) . . ?
N10 C11 C12 135.82(11) . . ?
C11 C12 H12 122.7 . . ?
C13 C12 C11 114.65(10) . . ?
C13 C12 H12 122.7 . . ?
C12 C13 H13 118.0 . . ?
C12 C13 C14 124.04(10) . . ?
C14 C13 H13 118.0 . . ?
C6 C14 C13 121.64(10) . . ?
C6 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
N10 C15 H15A 108.6 . . ?
N10 C15 H15B 108.6 . . ?
N10 C15 C16 114.50(9) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C17 C16 C15 124.66(10) . . ?
C17 C16 C21 119.14(11) . . ?
C21 C16 C15 116.20(10) . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.16(12) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.45(12) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.63(12) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.19(12) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.43(12) . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C4 120.71(10) . . ?
C27 C22 C4 121.41(10) . . ?
C27 C22 C23 117.87(10) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.23(11) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.10(11) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.51(11) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.35(11) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 H27 119.5 . . ?
C26 C27 C22 120.93(11) . . ?
C26 C27 H27 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 B3 C4 C5 128.06(11) . . . . ?
C2 B3 C4 C22 -53.53(12) . . . . ?
C2 B3 N8 C7 -130.24(10) . . . . ?
C2 B3 N8 N9 52.66(14) . . . . ?
B3 C4 C5 C6 -4.76(16) . . . . ?
B3 C4 C22 C23 -29.11(14) . . . . ?
B3 C4 C22 C27 149.45(10) . . . . ?
B3 N8 N9 N10 177.52(10) . . . . ?
C4 B3 N8 C7 -8.89(13) . . . . ?
C4 B3 N8 N9 174.01(10) . . . . ?
C4 C5 C6 C7 -1.90(15) . . . . ?
C4 C5 C6 C14 179.96(11) . . . . ?
C4 C22 C23 C24 179.97(10) . . . . ?
C4 C22 C27 C26 -179.52(10) . . . . ?
C5 C4 C22 C23 149.37(11) . . . . ?
C5 C4 C22 C27 -32.06(15) . . . . ?
C5 C6 C7 N8 2.47(16) . . . . ?
C5 C6 C7 C11 -176.47(10) . . . . ?
C5 C6 C14 C13 176.87(11) . . . . ?
C6 C7 N8 B3 3.83(17) . . . . ?
C6 C7 N8 N9 -178.63(10) . . . . ?
C6 C7 C11 N10 178.24(10) . . . . ?
C6 C7 C11 C12 -1.14(17) . . . . ?
C7 C6 C14 C13 -1.34(16) . . . . ?
C7 N8 N9 N10 0.16(12) . . . . ?
C7 C11 C12 C13 -0.39(16) . . . . ?
N8 B3 C4 C5 9.57(14) . . . . ?
N8 B3 C4 C22 -172.02(9) . . . . ?
N8 C7 C11 N10 -0.86(12) . . . . ?
N8 C7 C11 C12 179.76(10) . . . . ?
N8 N9 N10 C11 -0.75(12) . . . . ?
N8 N9 N10 C15 180.00(9) . . . . ?
N9 N10 C11 C7 1.00(12) . . . . ?
N9 N10 C11 C12 -179.76(12) . . . . ?
N9 N10 C15 C16 -113.40(11) . . . . ?
N10 C11 C12 C13 -179.52(12) . . . . ?
N10 C15 C16 C17 3.54(16) . . . . ?
N10 C15 C16 C21 -176.17(10) . . . . ?
C11 C7 N8 B3 -177.08(9) . . . . ?
C11 C7 N8 N9 0.47(12) . . . . ?
C11 N10 C15 C16 67.49(15) . . . . ?
C11 C12 C13 C14 0.95(17) . . . . ?
C12 C13 C14 C6 -0.05(18) . . . . ?
C14 C6 C7 N8 -179.10(10) . . . . ?
C14 C6 C7 C11 1.96(16) . . . . ?
C15 N10 C11 C7 -179.84(10) . . . . ?
C15 N10 C11 C12 -0.6(2) . . . . ?
C15 C16 C17 C18 -179.21(11) . . . . ?
C15 C16 C21 C20 179.69(11) . . . . ?
C16 C17 C18 C19 -0.47(19) . . . . ?
C17 C16 C21 C20 -0.03(17) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C19 C20 C21 0.48(19) . . . . ?
C19 C20 C21 C16 -0.45(19) . . . . ?
C21 C16 C17 C18 0.49(18) . . . . ?
C22 C4 C5 C6 176.87(9) . . . . ?
C22 C23 C24 C25 -1.03(17) . . . . ?
C23 C22 C27 C26 -0.92(16) . . . . ?
C23 C24 C25 C26 0.22(18) . . . . ?
C24 C25 C26 C27 0.21(18) . . . . ?
C25 C26 C27 C22 0.15(18) . . . . ?
C27 C22 C23 C24 1.36(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_n3_76
_database_code_depnum_ccdc_archive 'CCDC 2114086'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-05 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 B N4 O2'
_chemical_formula_sum            'C23 H19 B N4 O2'
_chemical_formula_weight         394.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.0625(3)
_cell_length_b                   11.3405(3)
_cell_length_c                   15.4611(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.428(2)
_cell_angle_gamma                90
_cell_volume                     1933.87(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7735
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      78.904
_cell_measurement_theta_min      4.747
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0977 before and 0.0838 after correction. The Ratio of minimum to maximum transmission is 0.8400. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23442
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.888
_diffrn_reflns_theta_min         4.746
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2991
_reflns_number_total             4097
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+0.5895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C24(H24), C26(H26)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40743(18) 0.73195(16) 0.76326(11) 0.0400(4) Uani 1 1 d . . . . .
H3 H 0.6987(14) 0.7076(13) 0.7324(10) 0.003(4) Uiso 1 1 d . . . . .
C2 C 0.4956(2) 0.69630(17) 0.73793(12) 0.0315(4) Uani 1 1 d . . . . .
B3 B 0.6191(2) 0.6470(2) 0.70499(14) 0.0303(5) Uani 1 1 d . . . . .
C4 C 0.64238(17) 0.50900(17) 0.72976(12) 0.0295(4) Uani 1 1 d . . . . .
C5 C 0.67090(18) 0.42639(17) 0.67181(12) 0.0309(4) Uani 1 1 d . . . . .
H5 H 0.690543 0.349044 0.691881 0.037 Uiso 1 1 calc R . . . .
C6 C 0.67255(17) 0.45170(16) 0.58018(12) 0.0288(4) Uani 1 1 d . . . . .
C7 C 0.64179(18) 0.56597(16) 0.55157(12) 0.0283(4) Uani 1 1 d . . . . .
N8 N 0.61307(15) 0.65833(13) 0.60236(10) 0.0286(4) Uani 1 1 d . . . . .
N9 N 0.58598(15) 0.75219(14) 0.55482(10) 0.0298(4) Uani 1 1 d . . . . .
N10 N 0.59693(15) 0.71990(13) 0.47180(10) 0.0285(4) Uani 1 1 d . . . . .
C11 C 0.63186(17) 0.60321(16) 0.46644(12) 0.0275(4) Uani 1 1 d . . . . .
C12 C 0.65308(18) 0.52341(17) 0.39945(13) 0.0308(4) Uani 1 1 d . . . . .
H12 H 0.645225 0.545409 0.339992 0.037 Uiso 1 1 calc R . . . .
C13 C 0.68598(18) 0.41139(18) 0.42613(13) 0.0329(4) Uani 1 1 d . . . . .
H13 H 0.702859 0.355234 0.383088 0.039 Uiso 1 1 calc R . . . .
C14 C 0.69614(18) 0.37497(17) 0.51384(13) 0.0315(4) Uani 1 1 d . . . . .
H14 H 0.719641 0.296182 0.527578 0.038 Uiso 1 1 calc R . . . .
C15 C 0.56667(18) 0.80261(16) 0.40361(12) 0.0289(4) Uani 1 1 d . . . . .
C16 C 0.48115(18) 0.89001(17) 0.41517(13) 0.0318(4) Uani 1 1 d . . . . .
H16 H 0.443169 0.895538 0.468074 0.038 Uiso 1 1 calc R . . . .
C17 C 0.45233(19) 0.96861(18) 0.34851(14) 0.0348(5) Uani 1 1 d . . . . .
H17 H 0.396675 1.030736 0.356511 0.042 Uiso 1 1 calc R . . . .
C18 C 0.5041(2) 0.95754(18) 0.26982(13) 0.0356(5) Uani 1 1 d . . . . .
H18 H 0.481240 1.009819 0.223401 0.043 Uiso 1 1 calc R . . . .
C19 C 0.5890(2) 0.87024(18) 0.25928(13) 0.0354(5) Uani 1 1 d . . . . .
H19 H 0.624599 0.863126 0.205554 0.042 Uiso 1 1 calc R . . . .
C20 C 0.62259(19) 0.79292(17) 0.32644(12) 0.0319(4) Uani 1 1 d . . . . .
H20 H 0.682686 0.734461 0.319800 0.038 Uiso 1 1 calc R . . . .
C21 C 0.63748(18) 0.47372(17) 0.82218(12) 0.0292(4) Uani 1 1 d . . . . .
C22 C 0.66022(18) 0.55607(17) 0.88856(12) 0.0290(4) Uani 1 1 d . . . . .
H22 H 0.675382 0.635988 0.874497 0.035 Uiso 1 1 calc R . . . .
C23 C 0.66090(17) 0.52244(16) 0.97468(12) 0.0285(4) Uani 1 1 d . . . . .
C24 C 0.63447(17) 0.40659(17) 0.99762(12) 0.0292(4) Uani 1 1 d . . . . .
H24 H 0.633770 0.383899 1.056726 0.035 Uiso 1 1 calc R . . . .
C25 C 0.60922(18) 0.32554(16) 0.93107(13) 0.0308(4) Uani 1 1 d . . . . .
C26 C 0.61129(18) 0.35733(17) 0.84463(12) 0.0308(4) Uani 1 1 d . . . . .
H26 H 0.594908 0.299999 0.800476 0.037 Uiso 1 1 calc R . . . .
O27 O 0.68928(13) 0.60987(12) 1.03393(8) 0.0332(3) Uani 1 1 d . . . . .
C28 C 0.7007(2) 0.57785(18) 1.12347(12) 0.0351(5) Uani 1 1 d . . . . .
H28A H 0.762423 0.516174 1.132821 0.053 Uiso 1 1 calc GR . . . .
H28B H 0.622792 0.548296 1.140496 0.053 Uiso 1 1 calc GR . . . .
H28C H 0.724905 0.647106 1.158576 0.053 Uiso 1 1 calc GR . . . .
O29 O 0.58052(15) 0.20944(12) 0.94539(9) 0.0403(4) Uani 1 1 d . . . . .
C30 C 0.5497(2) 0.17897(18) 1.03052(13) 0.0385(5) Uani 1 1 d . . . . .
H30A H 0.521704 0.096988 1.030903 0.058 Uiso 1 1 calc GR . . . .
H30B H 0.484997 0.231115 1.047567 0.058 Uiso 1 1 calc GR . . . .
H30C H 0.621175 0.187873 1.071534 0.058 Uiso 1 1 calc GR . . . .


_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 C2 1.152(3) . ?
C2 B3 1.596(3) . ?
B3 H3 1.171(16) . ?
B3 C4 1.626(3) . ?
B3 N8 1.588(3) . ?
C4 C5 1.350(3) . ?
C4 C21 1.489(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.447(3) . ?
C6 C7 1.403(3) . ?
C6 C14 1.385(3) . ?
C7 N8 1.361(2) . ?
C7 C11 1.379(3) . ?
N8 N9 1.315(2) . ?
N9 N10 1.349(2) . ?
N10 C11 1.383(2) . ?
N10 C15 1.431(2) . ?
C11 C12 1.409(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.414(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(3) . ?
C15 C20 1.390(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.396(3) . ?
C21 C26 1.401(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 C24 1.398(3) . ?
C23 O27 1.370(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(3) . ?
C25 C26 1.386(3) . ?
C25 O29 1.376(2) . ?
C26 H26 0.9500 . ?
O27 C28 1.427(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O29 C30 1.427(2) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 B3 178.7(2) . . ?
C2 B3 H3 108.5(8) . . ?
C2 B3 C4 112.73(17) . . ?
C4 B3 H3 112.2(8) . . ?
N8 B3 H3 106.6(8) . . ?
N8 B3 C2 108.64(16) . . ?
N8 B3 C4 107.88(16) . . ?
C5 C4 B3 123.51(17) . . ?
C5 C4 C21 118.56(18) . . ?
C21 C4 B3 117.87(16) . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.22(18) . . ?
C6 C5 H5 118.9 . . ?
C7 C6 C5 118.10(17) . . ?
C14 C6 C5 128.15(18) . . ?
C14 C6 C7 113.69(17) . . ?
N8 C7 C6 126.20(17) . . ?
N8 C7 C11 108.07(16) . . ?
C11 C7 C6 125.70(17) . . ?
C7 N8 B3 121.35(16) . . ?
N9 N8 B3 127.91(15) . . ?
N9 N8 C7 110.71(15) . . ?
N8 N9 N10 106.19(14) . . ?
N9 N10 C11 111.27(15) . . ?
N9 N10 C15 119.33(15) . . ?
C11 N10 C15 129.31(16) . . ?
C7 C11 N10 103.76(16) . . ?
C7 C11 C12 119.98(17) . . ?
N10 C11 C12 136.22(18) . . ?
C11 C12 H12 122.3 . . ?
C13 C12 C11 115.34(18) . . ?
C13 C12 H12 122.3 . . ?
C12 C13 H13 118.1 . . ?
C12 C13 C14 123.84(18) . . ?
C14 C13 H13 118.1 . . ?
C6 C14 C13 121.41(18) . . ?
C6 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 N10 119.66(17) . . ?
C20 C15 N10 119.08(18) . . ?
C20 C15 C16 121.25(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 118.94(19) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.53(19) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.82(19) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 120.6 . . ?
C19 C20 C15 118.74(19) . . ?
C19 C20 H20 120.6 . . ?
C22 C21 C4 120.53(17) . . ?
C22 C21 C26 118.50(17) . . ?
C26 C21 C4 120.97(17) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.67(18) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 121.15(17) . . ?
O27 C23 C22 115.33(16) . . ?
O27 C23 C24 123.52(17) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 C23 117.85(18) . . ?
C25 C24 H24 121.1 . . ?
C26 C25 C24 121.58(18) . . ?
O29 C25 C24 123.27(18) . . ?
O29 C25 C26 115.15(17) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 C21 120.20(17) . . ?
C25 C26 H26 119.9 . . ?
C23 O27 C28 117.59(15) . . ?
O27 C28 H28A 109.5 . . ?
O27 C28 H28B 109.5 . . ?
O27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 O29 C30 117.03(15) . . ?
O29 C30 H30A 109.5 . . ?
O29 C30 H30B 109.5 . . ?
O29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 B3 C4 C5 129.7(2) . . . . ?
C2 B3 C4 C21 -53.2(2) . . . . ?
C2 B3 N8 C7 -131.05(18) . . . . ?
C2 B3 N8 N9 51.5(2) . . . . ?
B3 C4 C5 C6 -5.7(3) . . . . ?
B3 C4 C21 C22 -24.7(3) . . . . ?
B3 C4 C21 C26 155.92(19) . . . . ?
B3 N8 N9 N10 177.92(17) . . . . ?
C4 B3 N8 C7 -8.5(2) . . . . ?
C4 B3 N8 N9 173.97(17) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C4 C5 C6 C14 -177.7(2) . . . . ?
C4 C21 C22 C23 -177.19(18) . . . . ?
C4 C21 C26 C25 178.85(18) . . . . ?
C5 C4 C21 C22 152.5(2) . . . . ?
C5 C4 C21 C26 -26.9(3) . . . . ?
C5 C6 C7 N8 1.9(3) . . . . ?
C5 C6 C7 C11 -175.99(19) . . . . ?
C5 C6 C14 C13 175.50(19) . . . . ?
C6 C7 N8 B3 3.7(3) . . . . ?
C6 C7 N8 N9 -178.48(18) . . . . ?
C6 C7 C11 N10 178.41(19) . . . . ?
C6 C7 C11 C12 0.2(3) . . . . ?
C7 C6 C14 C13 -1.5(3) . . . . ?
C7 N8 N9 N10 0.2(2) . . . . ?
C7 C11 C12 C13 -1.5(3) . . . . ?
N8 B3 C4 C5 9.8(3) . . . . ?
N8 B3 C4 C21 -173.17(16) . . . . ?
N8 C7 C11 N10 0.2(2) . . . . ?
N8 C7 C11 C12 -178.03(17) . . . . ?
N8 N9 N10 C11 -0.1(2) . . . . ?
N8 N9 N10 C15 176.68(16) . . . . ?
N9 N10 C11 C7 -0.1(2) . . . . ?
N9 N10 C11 C12 177.7(2) . . . . ?
N9 N10 C15 C16 -27.8(3) . . . . ?
N9 N10 C15 C20 152.95(17) . . . . ?
N10 C11 C12 C13 -179.0(2) . . . . ?
N10 C15 C16 C17 -179.54(17) . . . . ?
N10 C15 C20 C19 177.26(17) . . . . ?
C11 C7 N8 B3 -178.15(16) . . . . ?
C11 C7 N8 N9 -0.3(2) . . . . ?
C11 N10 C15 C16 148.3(2) . . . . ?
C11 N10 C15 C20 -30.9(3) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 C13 C14 C6 0.2(3) . . . . ?
C14 C6 C7 N8 179.26(19) . . . . ?
C14 C6 C7 C11 1.4(3) . . . . ?
C15 N10 C11 C7 -176.43(18) . . . . ?
C15 N10 C11 C12 1.4(4) . . . . ?
C15 C16 C17 C18 2.7(3) . . . . ?
C16 C15 C20 C19 -1.9(3) . . . . ?
C16 C17 C18 C19 -2.7(3) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C15 1.9(3) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?
C21 C4 C5 C6 177.24(18) . . . . ?
C21 C22 C23 C24 -2.4(3) . . . . ?
C21 C22 C23 O27 177.38(17) . . . . ?
C22 C21 C26 C25 -0.5(3) . . . . ?
C22 C23 C24 C25 1.0(3) . . . . ?
C22 C23 O27 C28 -175.12(17) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C23 C24 C25 O29 -179.20(18) . . . . ?
C24 C23 O27 C28 4.7(3) . . . . ?
C24 C25 C26 C21 -1.0(3) . . . . ?
C24 C25 O29 C30 14.1(3) . . . . ?
C26 C21 C22 C23 2.2(3) . . . . ?
C26 C25 O29 C30 -165.83(19) . . . . ?
O27 C23 C24 C25 -178.83(18) . . . . ?
O29 C25 C26 C21 178.98(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_n3_44
_database_code_depnum_ccdc_archive 'CCDC 2114505'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-07 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-10-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H14 B F6 N3 O4'
_chemical_formula_sum            'C24 H14 B F6 N3 O4'
_chemical_formula_weight         533.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8628(5)
_cell_length_b                   19.2303(8)
_cell_length_c                   11.1122(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.593(2)
_cell_angle_gamma                90
_cell_volume                     2305.02(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      79.77
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.645
_exptl_absorpt_coefficient_mu    1.203
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.792280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1076 before and 0.0562 after correction.
 
For component 2:
 wR2(int) was 0.1386 before and 0.0624 after correction.
 The Ratio of minimum to maximum transmission is 0.79.

Final HKLF 4 output contains 82547 reflections, Rint = 0.0412
 (65319 with I > 3sig(I), Rint = 0.0395)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4921
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.225
_diffrn_reflns_theta_min         4.098
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-II CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirrors
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4649
_reflns_number_total             4921
_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.
 
 The crystal was twinned. Detwinned data from integration with 
 Bruker-Saint were used  for refinement. 
 Twinning law (-5.33deg rotation) from Bruker-Saint:
 0.99826 -0.00091 -0.00390
 0.07689  0.99567  0.16562
 0.00237 -0.05171  0.99740
 TWINABS estimated twin fraction: 0.59:0.41 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+1.2676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C11(H11), C12(H12), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.72744(12) 0.56059(7) 0.24967(13) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.85325(11) 0.58188(6) 0.37751(11) 0.0168(2) Uani 1 1 d . . . . .
C3 C 0.88723(11) 0.55139(6) 0.49793(11) 0.0178(2) Uani 1 1 d . . . . .
H3 H 0.963874 0.564443 0.567521 0.021 Uiso 1 1 calc R U . . .
C4 C 0.81149(11) 0.49978(6) 0.52472(11) 0.0174(2) Uani 1 1 d . . . . .
C5 C 0.69958(11) 0.48133(6) 0.42044(11) 0.0164(2) Uani 1 1 d . . . . .
N6 N 0.65534(9) 0.50506(5) 0.29419(9) 0.0168(2) Uani 1 1 d . . . . .
N7 N 0.54762(9) 0.47620(5) 0.22023(10) 0.0188(2) Uani 1 1 d . . . . .
N8 N 0.52219(9) 0.43374(5) 0.30104(10) 0.0182(2) Uani 1 1 d . . . . .
C9 C 0.61423(11) 0.43455(6) 0.42776(11) 0.0175(2) Uani 1 1 d . . . . .
C10 C 0.63674(12) 0.39962(6) 0.54710(12) 0.0201(2) Uani 1 1 d . . . . .
H10 H 0.580099 0.367083 0.555335 0.024 Uiso 1 1 calc R U . . .
C11 C 0.74771(12) 0.41647(6) 0.65112(12) 0.0211(2) Uani 1 1 d . . . . .
H11 H 0.767963 0.393895 0.733572 0.025 Uiso 1 1 calc R U . . .
C12 C 0.83323(12) 0.46548(6) 0.64213(12) 0.0202(2) Uani 1 1 d . . . . .
H12 H 0.907184 0.475044 0.718366 0.024 Uiso 1 1 calc R U . . .
O13 O 0.64118(8) 0.61895(4) 0.18306(8) 0.01789(17) Uani 1 1 d . . . . .
C14 C 0.57444(11) 0.64891(6) 0.23703(12) 0.0196(2) Uani 1 1 d . . . . .
O15 O 0.57803(9) 0.64061(5) 0.34555(10) 0.0287(2) Uani 1 1 d . . . . .
C16 C 0.47967(12) 0.69848(7) 0.13603(14) 0.0258(3) Uani 1 1 d . . . . .
F17 F 0.53426(8) 0.74482(4) 0.08918(9) 0.0338(2) Uani 1 1 d . . . . .
F18 F 0.41532(9) 0.73299(5) 0.18980(10) 0.0467(3) Uani 1 1 d . . . . .
F19 F 0.39979(8) 0.66301(5) 0.03188(9) 0.0403(2) Uani 1 1 d . . . . .
O20 O 0.74775(8) 0.53200(4) 0.13577(8) 0.01795(17) Uani 1 1 d . . . . .
C21 C 0.80144(11) 0.47227(6) 0.13992(12) 0.0194(2) Uani 1 1 d . . . . .
O22 O 0.83696(9) 0.42991(5) 0.22719(9) 0.0285(2) Uani 1 1 d . . . . .
C23 C 0.81551(13) 0.46151(7) 0.00956(13) 0.0254(3) Uani 1 1 d . . . . .
F24 F 0.70549(8) 0.45968(5) -0.09333(8) 0.0356(2) Uani 1 1 d . . . . .
F25 F 0.87401(10) 0.40257(5) 0.01064(9) 0.0440(2) Uani 1 1 d . . . . .
F26 F 0.87918(10) 0.51348(5) -0.01147(10) 0.0442(2) Uani 1 1 d . . . . .
C27 C 0.93576(11) 0.63617(6) 0.36137(12) 0.0175(2) Uani 1 1 d . . . . .
C28 C 0.92251(11) 0.65753(6) 0.23555(12) 0.0212(2) Uani 1 1 d . . . . .
H28 H 0.859691 0.637064 0.159306 0.025 Uiso 1 1 calc R U . . .
C29 C 0.99940(13) 0.70809(7) 0.21982(13) 0.0256(3) Uani 1 1 d . . . . .
H29 H 0.988976 0.721174 0.133373 0.031 Uiso 1 1 calc R U . . .
C30 C 1.09094(13) 0.73949(7) 0.32908(14) 0.0262(3) Uani 1 1 d . . . . .
H30 H 1.142567 0.774430 0.318217 0.031 Uiso 1 1 calc R U . . .
C31 C 1.10596(12) 0.71900(7) 0.45488(13) 0.0242(3) Uani 1 1 d . . . . .
H31 H 1.168989 0.739786 0.530542 0.029 Uiso 1 1 calc R U . . .
C32 C 1.02980(11) 0.66847(6) 0.47103(12) 0.0207(2) Uani 1 1 d . . . . .
H32 H 1.041345 0.655424 0.557850 0.025 Uiso 1 1 calc R U . . .
C33 C 0.41124(11) 0.39253(6) 0.25146(12) 0.0190(2) Uani 1 1 d . . . . .
C34 C 0.38343(12) 0.35260(7) 0.13907(12) 0.0231(3) Uani 1 1 d . . . . .
H34 H 0.434285 0.354024 0.091917 0.028 Uiso 1 1 calc R U . . .
C35 C 0.27910(13) 0.31039(7) 0.09719(13) 0.0275(3) Uani 1 1 d . . . . .
H35 H 0.258729 0.281849 0.021221 0.033 Uiso 1 1 calc R U . . .
C36 C 0.20439(13) 0.30966(7) 0.16569(14) 0.0286(3) Uani 1 1 d . . . . .
H36 H 0.132663 0.281017 0.135782 0.034 Uiso 1 1 calc R U . . .
C37 C 0.23386(13) 0.35050(7) 0.27746(15) 0.0285(3) Uani 1 1 d . . . . .
H37 H 0.182136 0.349831 0.323656 0.034 Uiso 1 1 calc R U . . .
C38 C 0.33856(12) 0.39234(7) 0.32216(13) 0.0230(3) Uani 1 1 d . . . . .
H38 H 0.359960 0.420144 0.399203 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
B1 C2 1.6273(17) . ?
B1 N6 1.5713(16) . ?
B1 O13 1.4913(15) . ?
B1 O20 1.4887(15) . ?
C2 C3 1.3594(17) . ?
C2 C27 1.4921(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.4503(17) . ?
C4 C5 1.3966(16) . ?
C4 C12 1.3870(16) . ?
C5 N6 1.3561(14) . ?
C5 C9 1.3818(17) . ?
N6 N7 1.3199(14) . ?
N7 N8 1.3378(14) . ?
N8 C9 1.3768(15) . ?
N8 C33 1.4354(15) . ?
C9 C10 1.4094(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3811(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.4184(18) . ?
C12 H12 0.9500 . ?
O13 C14 1.3090(15) . ?
C14 O15 1.1994(16) . ?
C14 C16 1.5435(17) . ?
C16 F17 1.3286(16) . ?
C16 F18 1.3265(16) . ?
C16 F19 1.3379(16) . ?
O20 C21 1.3048(15) . ?
C21 O22 1.2007(15) . ?
C21 C23 1.5396(17) . ?
C23 F24 1.3304(16) . ?
C23 F25 1.3266(15) . ?
C23 F26 1.3307(17) . ?
C27 C28 1.4019(17) . ?
C27 C32 1.4085(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.3931(18) . ?
C29 H29 0.9500 . ?
C29 C30 1.3858(19) . ?
C30 H30 0.9500 . ?
C30 C31 1.391(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.3884(18) . ?
C32 H32 0.9500 . ?
C33 C34 1.3839(17) . ?
C33 C38 1.3871(18) . ?
C34 H34 0.9500 . ?
C34 C35 1.3884(19) . ?
C35 H35 0.9500 . ?
C35 C36 1.388(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.386(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.3868(18) . ?
C38 H38 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
N6 B1 C2 108.53(9) . . ?
O13 B1 C2 115.76(10) . . ?
O13 B1 N6 108.46(9) . . ?
O20 B1 C2 114.90(10) . . ?
O20 B1 N6 108.57(9) . . ?
O20 B1 O13 100.16(9) . . ?
C3 C2 B1 122.64(11) . . ?
C3 C2 C27 118.65(11) . . ?
C27 C2 B1 118.70(10) . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.81(11) . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 117.37(10) . . ?
C12 C4 C3 129.04(11) . . ?
C12 C4 C5 113.58(11) . . ?
N6 C5 C4 126.71(11) . . ?
N6 C5 C9 107.60(10) . . ?
C9 C5 C4 125.69(11) . . ?
C5 N6 B1 121.83(10) . . ?
N7 N6 B1 127.05(9) . . ?
N7 N6 C5 111.12(10) . . ?
N6 N7 N8 105.60(9) . . ?
N7 N8 C9 112.04(10) . . ?
N7 N8 C33 120.42(10) . . ?
C9 N8 C33 127.52(10) . . ?
C5 C9 C10 120.60(11) . . ?
N8 C9 C5 103.64(10) . . ?
N8 C9 C10 135.73(11) . . ?
C9 C10 H10 122.7 . . ?
C11 C10 C9 114.64(11) . . ?
C11 C10 H10 122.7 . . ?
C10 C11 H11 118.1 . . ?
C10 C11 C12 123.89(11) . . ?
C12 C11 H11 118.1 . . ?
C4 C12 C11 121.58(11) . . ?
C4 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 O13 B1 121.65(9) . . ?
O13 C14 C16 109.58(10) . . ?
O15 C14 O13 128.82(12) . . ?
O15 C14 C16 121.57(11) . . ?
F17 C16 C14 111.89(10) . . ?
F17 C16 F19 106.75(11) . . ?
F18 C16 C14 111.28(11) . . ?
F18 C16 F17 107.86(11) . . ?
F18 C16 F19 108.15(11) . . ?
F19 C16 C14 110.70(11) . . ?
C21 O20 B1 122.99(9) . . ?
O20 C21 C23 109.12(10) . . ?
O22 C21 O20 128.89(12) . . ?
O22 C21 C23 121.99(11) . . ?
F24 C23 C21 111.13(11) . . ?
F24 C23 F26 107.13(11) . . ?
F25 C23 C21 111.56(11) . . ?
F25 C23 F24 107.91(11) . . ?
F25 C23 F26 108.08(11) . . ?
F26 C23 C21 110.86(11) . . ?
C28 C27 C2 121.20(11) . . ?
C28 C27 C32 116.95(11) . . ?
C32 C27 C2 121.85(11) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 C27 121.48(12) . . ?
C29 C28 H28 119.3 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.63(12) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 120.6 . . ?
C29 C30 C31 118.88(12) . . ?
C31 C30 H30 120.6 . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.68(12) . . ?
C32 C31 H31 119.7 . . ?
C27 C32 H32 119.3 . . ?
C31 C32 C27 121.37(12) . . ?
C31 C32 H32 119.3 . . ?
C34 C33 N8 119.27(11) . . ?
C34 C33 C38 122.59(12) . . ?
C38 C33 N8 118.09(11) . . ?
C33 C34 H34 120.9 . . ?
C33 C34 C35 118.12(12) . . ?
C35 C34 H34 120.9 . . ?
C34 C35 H35 119.8 . . ?
C36 C35 C34 120.37(13) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.35(12) . . ?
C37 C36 H36 119.8 . . ?
C36 C37 H37 119.9 . . ?
C36 C37 C38 120.28(13) . . ?
C38 C37 H37 119.9 . . ?
C33 C38 H38 120.9 . . ?
C37 C38 C33 118.28(12) . . ?
C37 C38 H38 120.9 . . ?

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
B1 C2 C3 C4 -3.13(18) . . . . ?
B1 C2 C27 C28 -14.27(16) . . . . ?
B1 C2 C27 C32 165.44(11) . . . . ?
B1 N6 N7 N8 -178.61(10) . . . . ?
B1 O13 C14 O15 7.26(19) . . . . ?
B1 O13 C14 C16 -170.74(10) . . . . ?
B1 O20 C21 O22 3.9(2) . . . . ?
B1 O20 C21 C23 -175.94(10) . . . . ?
C2 B1 N6 C5 -0.91(14) . . . . ?
C2 B1 N6 N7 178.14(10) . . . . ?
C2 B1 O13 C14 -72.63(14) . . . . ?
C2 B1 O20 C21 67.14(14) . . . . ?
C2 C3 C4 C5 0.30(17) . . . . ?
C2 C3 C4 C12 -178.84(12) . . . . ?
C2 C27 C28 C29 -179.88(11) . . . . ?
C2 C27 C32 C31 -179.92(11) . . . . ?
C3 C2 C27 C28 164.68(11) . . . . ?
C3 C2 C27 C32 -15.60(17) . . . . ?
C3 C4 C5 N6 2.32(18) . . . . ?
C3 C4 C5 C9 -178.44(11) . . . . ?
C3 C4 C12 C11 179.39(11) . . . . ?
C4 C5 N6 B1 -1.80(18) . . . . ?
C4 C5 N6 N7 179.02(11) . . . . ?
C4 C5 C9 N8 -179.35(11) . . . . ?
C4 C5 C9 C10 -1.07(19) . . . . ?
C5 C4 C12 C11 0.22(17) . . . . ?
C5 N6 N7 N8 0.52(13) . . . . ?
C5 C9 C10 C11 0.18(17) . . . . ?
N6 B1 C2 C3 3.27(15) . . . . ?
N6 B1 C2 C27 -177.82(9) . . . . ?
N6 B1 O13 C14 49.58(14) . . . . ?
N6 B1 O20 C21 -54.55(14) . . . . ?
N6 C5 C9 N8 0.01(13) . . . . ?
N6 C5 C9 C10 178.29(10) . . . . ?
N6 N7 N8 C9 -0.52(13) . . . . ?
N6 N7 N8 C33 -178.77(10) . . . . ?
N7 N8 C9 C5 0.32(13) . . . . ?
N7 N8 C9 C10 -177.56(13) . . . . ?
N7 N8 C33 C34 50.46(16) . . . . ?
N7 N8 C33 C38 -132.13(12) . . . . ?
N8 C9 C10 C11 177.78(13) . . . . ?
N8 C33 C34 C35 176.65(11) . . . . ?
N8 C33 C38 C37 -177.54(11) . . . . ?
C9 C5 N6 B1 178.85(10) . . . . ?
C9 C5 N6 N7 -0.34(13) . . . . ?
C9 N8 C33 C34 -127.50(13) . . . . ?
C9 N8 C33 C38 49.91(17) . . . . ?
C9 C10 C11 C12 0.85(18) . . . . ?
C10 C11 C12 C4 -1.09(19) . . . . ?
C12 C4 C5 N6 -178.41(11) . . . . ?
C12 C4 C5 C9 0.83(17) . . . . ?
O13 B1 C2 C3 125.45(12) . . . . ?
O13 B1 C2 C27 -55.64(14) . . . . ?
O13 B1 N6 C5 -127.43(11) . . . . ?
O13 B1 N6 N7 51.62(15) . . . . ?
O13 B1 O20 C21 -168.11(10) . . . . ?
O13 C14 C16 F17 -55.46(14) . . . . ?
O13 C14 C16 F18 -176.21(11) . . . . ?
O13 C14 C16 F19 63.48(14) . . . . ?
O15 C14 C16 F17 126.37(13) . . . . ?
O15 C14 C16 F18 5.62(18) . . . . ?
O15 C14 C16 F19 -114.69(14) . . . . ?
O20 B1 C2 C3 -118.45(12) . . . . ?
O20 B1 C2 C27 60.46(14) . . . . ?
O20 B1 N6 C5 124.61(11) . . . . ?
O20 B1 N6 N7 -56.34(14) . . . . ?
O20 B1 O13 C14 163.22(10) . . . . ?
O20 C21 C23 F24 -61.91(14) . . . . ?
O20 C21 C23 F25 177.62(11) . . . . ?
O20 C21 C23 F26 57.11(14) . . . . ?
O22 C21 C23 F24 118.23(14) . . . . ?
O22 C21 C23 F25 -2.25(18) . . . . ?
O22 C21 C23 F26 -122.75(14) . . . . ?
C27 C2 C3 C4 177.96(10) . . . . ?
C27 C28 C29 C30 -0.8(2) . . . . ?
C28 C27 C32 C31 -0.19(17) . . . . ?
C28 C29 C30 C31 0.9(2) . . . . ?
C29 C30 C31 C32 -0.7(2) . . . . ?
C30 C31 C32 C27 0.35(19) . . . . ?
C32 C27 C28 C29 0.39(18) . . . . ?
C33 N8 C9 C5 178.42(11) . . . . ?
C33 N8 C9 C10 0.5(2) . . . . ?
C33 C34 C35 C36 1.09(19) . . . . ?
C34 C33 C38 C37 -0.22(19) . . . . ?
C34 C35 C36 C37 -0.7(2) . . . . ?
C35 C36 C37 C38 -0.2(2) . . . . ?
C36 C37 C38 C33 0.6(2) . . . . ?
C38 C33 C34 C35 -0.64(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT992_n3_44               
;
PROBLEM: Repd & Actual _reflns_number_gt Values Differ by         43 Check 
RESPONSE: According to Shelxl there are 4649 reflections with Fo > 4sig(Fo).
;
# end Validation Reply Form
####################################################################### 
# 
# 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_QT_N3_24
_database_code_depnum_ccdc_archive 'CCDC 2113571'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 B N4 S, C H Cl3'
_chemical_formula_sum            'C20 H14 B Cl3 N4 S'
_chemical_formula_weight         459.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5849(6)
_cell_length_b                   9.6966(6)
_cell_length_c                   12.5042(7)
_cell_angle_alpha                102.614(2)
_cell_angle_beta                 92.073(2)
_cell_angle_gamma                115.981(2)
_cell_volume                     1007.91(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.77
_cell_measurement_theta_min      3.66
_shelx_estimated_absorpt_T_max   0.819
_shelx_estimated_absorpt_T_min   0.490
_exptl_absorpt_coefficient_mu    5.205
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0644 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.8361.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20495
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.354
_diffrn_reflns_theta_min         3.664
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4074
_reflns_number_total             4261
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4261
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+0.4754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0663
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H32-H5
 -2.2 with sigma of 0.02
 C4-C31 \\sim C4-C21
 with sigma of 0.01
3. Restrained planarity
 C4, C31, C32, S33, C34, C35
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(S23) = Uanis(C34)
Uanis(C31) = Uanis(C21)
5. Rigid body (RIGU) restrains
 C21, C22, S23, C24, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C31, C32, S33, C34, C35
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Same fragment restrains
{C21, C22, S23, C24, C25} sigma for 1-2: 0.01, 1-3: 0.04
as in
{C31, C32, S33, C34, C35}
7. Others
 Sof(C31)=Sof(C32)=Sof(H32)=Sof(S33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=1-
 FVAR(1)
 Sof(C21)=Sof(C22)=Sof(H22)=Sof(S23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=FVAR(1)
8.a Ternary CH refined with riding coordinates:
 C41(H41)
8.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C24(H24), C25(H25), C32(H32), C34(H34), C35(H35)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.03576(14) 0.73126(15) 0.28058(10) 0.0243(2) Uani 1 1 d . . . . .
C2 C 0.94780(14) 0.70191(15) 0.34218(10) 0.0165(2) Uani 1 1 d . . . . .
B3 B 0.82295(16) 0.66754(16) 0.42717(11) 0.0150(3) Uani 1 1 d . . . . .
H3 H 0.8009(18) 0.7724(19) 0.4501(13) 0.017(4) Uiso 1 1 d . . . . .
C4 C 0.87687(14) 0.62275(15) 0.53408(10) 0.0152(2) Uani 1 1 d D . . . .
C5 C 0.79064(15) 0.48721(15) 0.56437(10) 0.0166(2) Uani 1 1 d . . . . .
H5 H 0.828417 0.471771 0.629801 0.020 Uiso 1 1 calc DR U . . .
C6 C 0.64205(14) 0.36514(15) 0.49926(10) 0.0158(2) Uani 1 1 d . . . . .
C7 C 0.58913(14) 0.39288(14) 0.40364(10) 0.0146(2) Uani 1 1 d . . . . .
N8 N 0.66347(12) 0.52213(12) 0.36387(8) 0.0146(2) Uani 1 1 d . . . . .
N9 N 0.58247(12) 0.50742(12) 0.27099(8) 0.0160(2) Uani 1 1 d . . . . .
N10 N 0.45436(12) 0.36586(12) 0.25066(8) 0.0152(2) Uani 1 1 d . . . . .
C11 C 0.45211(14) 0.28864(15) 0.33120(10) 0.0151(2) Uani 1 1 d . . . . .
C12 C 0.35260(14) 0.14000(15) 0.34886(10) 0.0174(2) Uani 1 1 d . . . . .
H12 H 0.258731 0.065513 0.300006 0.021 Uiso 1 1 calc R U . . .
C13 C 0.40241(15) 0.11136(15) 0.44272(11) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.339301 0.012893 0.458606 0.023 Uiso 1 1 calc R U . . .
C14 C 0.54238(15) 0.22011(15) 0.51717(11) 0.0187(2) Uani 1 1 d . . . . .
H14 H 0.568191 0.192574 0.580828 0.022 Uiso 1 1 calc R U . . .
C15 C 0.34245(14) 0.31264(14) 0.15296(10) 0.0154(2) Uani 1 1 d . . . . .
C16 C 0.39591(15) 0.33019(15) 0.05278(10) 0.0176(2) Uani 1 1 d . . . . .
H16 H 0.505069 0.376125 0.048440 0.021 Uiso 1 1 calc R U . . .
C17 C 0.28626(16) 0.27912(16) -0.04089(11) 0.0199(3) Uani 1 1 d . . . . .
H17 H 0.320333 0.291158 -0.110196 0.024 Uiso 1 1 calc R U . . .
C18 C 0.12664(15) 0.21036(15) -0.03387(11) 0.0204(3) Uani 1 1 d . . . . .
H18 H 0.052171 0.174440 -0.098556 0.024 Uiso 1 1 calc R U . . .
C19 C 0.07564(15) 0.19398(16) 0.06731(11) 0.0200(3) Uani 1 1 d . . . . .
H19 H -0.033532 0.147284 0.071636 0.024 Uiso 1 1 calc R U . . .
C20 C 0.18383(15) 0.24571(15) 0.16222(10) 0.0178(2) Uani 1 1 d . . . . .
H20 H 0.150038 0.235499 0.231839 0.021 Uiso 1 1 calc R U . . .
C21 C 1.0267(2) 0.7413(5) 0.6045(2) 0.0162(4) Uani 0.822(2) 1 d D . P A 1
C22 C 1.1005(5) 0.8964(5) 0.6008(4) 0.0218(8) Uani 0.822(2) 1 d D . P A 1
H22 H 1.062657 0.937049 0.550325 0.026 Uiso 0.822(2) 1 calc R U P A 1
S23 S 1.26681(5) 1.01017(7) 0.69529(5) 0.02546(16) Uani 0.822(2) 1 d D . P A 1
C24 C 1.2457(10) 0.8503(9) 0.7430(9) 0.0284(14) Uani 0.822(2) 1 d D . P A 1
H24 H 1.316463 0.854529 0.800276 0.034 Uiso 0.822(2) 1 calc R U P A 1
C25 C 1.1137(4) 0.7159(6) 0.6881(3) 0.0193(9) Uani 0.822(2) 1 d D . P A 1
H25 H 1.082535 0.615642 0.703522 0.023 Uiso 0.822(2) 1 calc R U P A 1
C31 C 1.0220(9) 0.749(2) 0.6040(9) 0.0162(4) Uani 0.178(2) 1 d D . P A 2
C32 C 1.1081(14) 0.716(2) 0.6738(13) 0.017(3) Uani 0.178(2) 1 d D . P A 2
H32 H 1.079752 0.612101 0.680882 0.020 Uiso 0.178(2) 1 calc DR U P A 2
S33 S 1.2719(12) 0.8798(11) 0.7475(10) 0.0294(13) Uani 0.178(2) 1 d D . P A 2
C34 C 1.2243(14) 0.9954(16) 0.6830(11) 0.02546(16) Uani 0.178(2) 1 d D . P A 2
H34 H 1.287136 1.107123 0.698018 0.031 Uiso 0.178(2) 1 calc R U P A 2
C35 C 1.0891(19) 0.915(2) 0.6083(15) 0.016(3) Uani 0.178(2) 1 d D . P A 2
H35 H 1.046420 0.961608 0.565904 0.019 Uiso 0.178(2) 1 calc R U P A 2
C41 C 1.22807(15) 0.72180(15) 0.07472(10) 0.0184(2) Uani 1 1 d . . . . .
H41 H 1.130456 0.705035 0.108052 0.022 Uiso 1 1 calc R U . . .
Cl42 Cl 1.17411(4) 0.59365(4) -0.06044(2) 0.02104(8) Uani 1 1 d . . . . .
Cl43 Cl 1.32595(4) 0.92164(4) 0.06840(3) 0.02659(9) Uani 1 1 d . . . . .
Cl44 Cl 1.34748(4) 0.67953(5) 0.15896(3) 0.02927(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.1479(17) . ?
C2 B3 1.6030(18) . ?
B3 H3 1.107(16) . ?
B3 C4 1.6258(18) . ?
B3 N8 1.5773(17) . ?
C4 C5 1.3573(17) . ?
C4 C21 1.477(2) . ?
C4 C31 1.468(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.4527(17) . ?
C6 C7 1.4056(16) . ?
C6 C14 1.3844(17) . ?
C7 N8 1.3569(15) . ?
C7 C11 1.3849(17) . ?
N8 N9 1.3180(14) . ?
N9 N10 1.3434(14) . ?
N10 C11 1.3754(15) . ?
N10 C15 1.4333(15) . ?
C11 C12 1.4091(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3786(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.4212(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3870(17) . ?
C15 C20 1.3882(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3869(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3908(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.3890(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3895(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.366(3) . ?
C21 C25 1.441(4) . ?
C22 H22 0.9500 . ?
C22 S23 1.705(4) . ?
S23 C24 1.714(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.368(8) . ?
C25 H25 0.9500 . ?
C31 C32 1.358(11) . ?
C31 C35 1.434(11) . ?
C32 H32 0.9500 . ?
C32 S33 1.704(10) . ?
S33 C34 1.713(9) . ?
C34 H34 0.9500 . ?
C34 C35 1.367(13) . ?
C35 H35 0.9500 . ?
C41 H41 1.0000 . ?
C41 Cl42 1.7676(13) . ?
C41 Cl43 1.7666(13) . ?
C41 Cl44 1.7606(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 B3 177.21(13) . . ?
C2 B3 H3 107.2(8) . . ?
C2 B3 C4 113.30(10) . . ?
C4 B3 H3 113.0(8) . . ?
N8 B3 C2 108.20(10) . . ?
N8 B3 H3 107.1(8) . . ?
N8 B3 C4 107.76(10) . . ?
C5 C4 B3 124.28(11) . . ?
C5 C4 C21 118.5(2) . . ?
C5 C4 C31 121.1(10) . . ?
C21 C4 B3 117.2(2) . . ?
C31 C4 B3 114.4(10) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.67(11) . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 117.55(11) . . ?
C14 C6 C5 128.85(11) . . ?
C14 C6 C7 113.60(11) . . ?
N8 C7 C6 126.82(11) . . ?
N8 C7 C11 107.90(10) . . ?
C11 C7 C6 125.25(11) . . ?
C7 N8 B3 121.77(10) . . ?
N9 N8 B3 127.42(10) . . ?
N9 N8 C7 110.78(10) . . ?
N8 N9 N10 105.93(9) . . ?
N9 N10 C11 111.84(10) . . ?
N9 N10 C15 119.72(10) . . ?
C11 N10 C15 128.44(10) . . ?
C7 C11 C12 120.85(11) . . ?
N10 C11 C7 103.54(10) . . ?
N10 C11 C12 135.55(12) . . ?
C11 C12 H12 122.7 . . ?
C13 C12 C11 114.61(11) . . ?
C13 C12 H12 122.7 . . ?
C12 C13 H13 118.0 . . ?
C12 C13 C14 124.02(12) . . ?
C14 C13 H13 118.0 . . ?
C6 C14 C13 121.66(11) . . ?
C6 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C16 C15 N10 119.11(11) . . ?
C16 C15 C20 122.28(11) . . ?
C20 C15 N10 118.61(11) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.44(11) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.32(12) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.30(12) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.19(12) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 118.47(12) . . ?
C15 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C22 C21 C4 123.2(4) . . ?
C22 C21 C25 110.0(2) . . ?
C25 C21 C4 126.8(3) . . ?
C21 C22 H22 123.2 . . ?
C21 C22 S23 113.7(2) . . ?
S23 C22 H22 123.2 . . ?
C22 S23 C24 91.6(3) . . ?
S23 C24 H24 124.3 . . ?
C25 C24 S23 111.3(5) . . ?
C25 C24 H24 124.3 . . ?
C21 C25 H25 123.3 . . ?
C24 C25 C21 113.4(4) . . ?
C24 C25 H25 123.3 . . ?
C32 C31 C4 121.1(15) . . ?
C32 C31 C35 112.7(9) . . ?
C35 C31 C4 126.2(16) . . ?
C31 C32 H32 123.2 . . ?
C31 C32 S33 113.6(10) . . ?
S33 C32 H32 123.2 . . ?
C32 S33 C34 89.6(10) . . ?
S33 C34 H34 122.5 . . ?
C35 C34 S33 115.0(13) . . ?
C35 C34 H34 122.5 . . ?
C31 C35 H35 125.4 . . ?
C34 C35 C31 109.1(12) . . ?
C34 C35 H35 125.4 . . ?
Cl42 C41 H41 108.5 . . ?
Cl43 C41 H41 108.5 . . ?
Cl43 C41 Cl42 109.84(7) . . ?
Cl44 C41 H41 108.5 . . ?
Cl44 C41 Cl42 110.86(7) . . ?
Cl44 C41 Cl43 110.56(7) . . ?

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
C2 B3 C4 C5 -123.69(13) . . . . ?
C2 B3 C4 C21 58.85(18) . . . . ?
C2 B3 C4 C31 62.2(5) . . . . ?
C2 B3 N8 C7 126.95(11) . . . . ?
C2 B3 N8 N9 -54.82(15) . . . . ?
B3 C4 C5 C6 2.57(19) . . . . ?
B3 C4 C21 C22 16.3(3) . . . . ?
B3 C4 C21 C25 -166.0(2) . . . . ?
B3 C4 C31 C32 -159.2(7) . . . . ?
B3 C4 C31 C35 20.8(7) . . . . ?
B3 N8 N9 N10 -178.69(10) . . . . ?
C4 B3 N8 C7 4.10(15) . . . . ?
C4 B3 N8 N9 -177.66(10) . . . . ?
C4 C5 C6 C7 -0.66(18) . . . . ?
C4 C5 C6 C14 178.51(13) . . . . ?
C4 C21 C22 S23 177.08(18) . . . . ?
C4 C21 C25 C24 -177.5(5) . . . . ?
C4 C31 C32 S33 -179.9(2) . . . . ?
C4 C31 C35 C34 -179.9(3) . . . . ?
C5 C4 C21 C22 -161.3(2) . . . . ?
C5 C4 C21 C25 16.4(3) . . . . ?
C5 C4 C31 C32 26.5(8) . . . . ?
C5 C4 C31 C35 -153.5(8) . . . . ?
C5 C6 C7 N8 0.93(18) . . . . ?
C5 C6 C7 C11 178.82(11) . . . . ?
C5 C6 C14 C13 -177.99(12) . . . . ?
C6 C7 N8 B3 -3.05(18) . . . . ?
C6 C7 N8 N9 178.45(11) . . . . ?
C6 C7 C11 N10 -178.33(11) . . . . ?
C6 C7 C11 C12 -0.64(19) . . . . ?
C7 C6 C14 C13 1.21(18) . . . . ?
C7 N8 N9 N10 -0.30(13) . . . . ?
C7 C11 C12 C13 0.94(17) . . . . ?
N8 B3 C4 C5 -4.02(16) . . . . ?
N8 B3 C4 C21 178.52(14) . . . . ?
N8 B3 C4 C31 -178.1(5) . . . . ?
N8 C7 C11 N10 -0.10(13) . . . . ?
N8 C7 C11 C12 177.59(11) . . . . ?
N8 N9 N10 C11 0.24(13) . . . . ?
N8 N9 N10 C15 -178.81(10) . . . . ?
N9 N10 C11 C7 -0.09(13) . . . . ?
N9 N10 C11 C12 -177.24(13) . . . . ?
N9 N10 C15 C16 44.36(16) . . . . ?
N9 N10 C15 C20 -135.38(12) . . . . ?
N10 C11 C12 C13 177.73(13) . . . . ?
N10 C15 C16 C17 -179.57(11) . . . . ?
N10 C15 C20 C19 -179.89(11) . . . . ?
C11 C7 N8 B3 178.75(10) . . . . ?
C11 C7 N8 N9 0.25(13) . . . . ?
C11 N10 C15 C16 -134.51(13) . . . . ?
C11 N10 C15 C20 45.75(18) . . . . ?
C11 C12 C13 C14 -0.20(19) . . . . ?
C12 C13 C14 C6 -0.9(2) . . . . ?
C14 C6 C7 N8 -178.36(12) . . . . ?
C14 C6 C7 C11 -0.47(18) . . . . ?
C15 N10 C11 C7 178.85(11) . . . . ?
C15 N10 C11 C12 1.7(2) . . . . ?
C15 C16 C17 C18 -0.74(19) . . . . ?
C16 C15 C20 C19 0.38(19) . . . . ?
C16 C17 C18 C19 0.8(2) . . . . ?
C17 C18 C19 C20 -0.2(2) . . . . ?
C18 C19 C20 C15 -0.34(19) . . . . ?
C20 C15 C16 C17 0.16(19) . . . . ?
C21 C4 C5 C6 180.00(16) . . . . ?
C21 C22 S23 C24 1.0(4) . . . . ?
C22 C21 C25 C24 0.5(5) . . . . ?
C22 S23 C24 C25 -0.7(6) . . . . ?
S23 C24 C25 C21 0.3(7) . . . . ?
C25 C21 C22 S23 -1.0(3) . . . . ?
C31 C4 C5 C6 176.3(6) . . . . ?
C31 C32 S33 C34 -0.2(3) . . . . ?
C32 C31 C35 C34 0.1(5) . . . . ?
C32 S33 C34 C35 0.2(5) . . . . ?
S33 C34 C35 C31 -0.2(7) . . . . ?
C35 C31 C32 S33 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_QT_N3_4
_database_code_depnum_ccdc_archive 'CCDC 2113570'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 B N3'
_chemical_formula_sum            'C20 H16 B N3'
_chemical_formula_weight         309.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.7975(2)
_cell_length_b                   8.0452(2)
_cell_length_c                   29.5872(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.7970(10)
_cell_angle_gamma                90
_cell_volume                     1609.77(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.58
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0629 after correction.
The Ratio of minimum to maximum transmission is 0.9109.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            23744
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.854
_diffrn_reflns_theta_min         3.002
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2897
_reflns_number_total             3446
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.7217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B3 B 0.3029(2) 0.84748(16) 0.54524(5) 0.0162(3) Uani 1 1 d . . . . .
H3A H 0.432(2) 0.9314(19) 0.5409(5) 0.023(4) Uiso 1 1 d . . . . .
H3B H 0.169(2) 0.927(2) 0.5502(5) 0.026(4) Uiso 1 1 d . . . . .
C4 C 0.34448(17) 0.71643(15) 0.58648(4) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.33251(17) 0.54875(15) 0.58273(4) 0.0163(2) Uani 1 1 d . . . . .
H5 H 0.354981 0.482016 0.609234 0.020 Uiso 1 1 calc R U . . .
C6 C 0.28597(17) 0.46948(15) 0.53892(4) 0.0153(2) Uani 1 1 d . . . . .
C7 C 0.25122(17) 0.57285(14) 0.50072(4) 0.0148(2) Uani 1 1 d . . . . .
N8 N 0.25560(15) 0.74212(12) 0.50001(3) 0.0149(2) Uani 1 1 d . . . . .
N9 N 0.21435(15) 0.79785(12) 0.45839(3) 0.0164(2) Uani 1 1 d . . . . .
N10 N 0.18244(15) 0.66218(12) 0.43172(3) 0.0162(2) Uani 1 1 d . . . . .
C11 C 0.20319(17) 0.51738(15) 0.45664(4) 0.0154(2) Uani 1 1 d . . . . .
C12 C 0.18199(18) 0.34652(15) 0.44726(4) 0.0170(3) Uani 1 1 d . . . . .
H12 H 0.145607 0.305397 0.417491 0.020 Uiso 1 1 calc R U . . .
C13 C 0.21777(18) 0.24276(15) 0.48437(4) 0.0176(3) Uani 1 1 d . . . . .
H13 H 0.206553 0.126207 0.479641 0.021 Uiso 1 1 calc R U . . .
C14 C 0.27033(18) 0.30125(14) 0.52912(4) 0.0167(2) Uani 1 1 d . . . . .
H14 H 0.295553 0.223046 0.553060 0.020 Uiso 1 1 calc R U . . .
C15 C 0.11764(18) 0.68099(15) 0.38448(4) 0.0177(3) Uani 1 1 d . . . . .
C16 C -0.01317(19) 0.80786(17) 0.37069(5) 0.0224(3) Uani 1 1 d . . . . .
H16 H -0.053995 0.885614 0.392037 0.027 Uiso 1 1 calc R U . . .
C17 C -0.0833(2) 0.81881(19) 0.32495(5) 0.0275(3) Uani 1 1 d . . . . .
H17 H -0.172392 0.905219 0.314874 0.033 Uiso 1 1 calc R U . . .
C18 C -0.0239(2) 0.70435(19) 0.29395(5) 0.0275(3) Uani 1 1 d . . . . .
H18 H -0.074856 0.710970 0.262899 0.033 Uiso 1 1 calc R U . . .
C19 C 0.1100(2) 0.58003(17) 0.30836(5) 0.0250(3) Uani 1 1 d . . . . .
H19 H 0.152354 0.503276 0.286940 0.030 Uiso 1 1 calc R U . . .
C20 C 0.18238(19) 0.56723(16) 0.35380(4) 0.0203(3) Uani 1 1 d . . . . .
H20 H 0.274163 0.482589 0.363749 0.024 Uiso 1 1 calc R U . . .
C21 C 0.39757(18) 0.78562(15) 0.63268(4) 0.0175(3) Uani 1 1 d . . . . .
C22 C 0.5324(2) 0.91710(17) 0.63973(5) 0.0231(3) Uani 1 1 d . . . . .
H22 H 0.585372 0.966943 0.614489 0.028 Uiso 1 1 calc R U . . .
C23 C 0.5894(2) 0.97529(19) 0.68339(5) 0.0281(3) Uani 1 1 d . . . . .
H23 H 0.683036 1.062925 0.687756 0.034 Uiso 1 1 calc R U . . .
C24 C 0.5106(2) 0.90640(18) 0.72060(5) 0.0266(3) Uani 1 1 d . . . . .
H24 H 0.550252 0.946078 0.750372 0.032 Uiso 1 1 calc R U . . .
C25 C 0.3735(2) 0.77924(17) 0.71389(5) 0.0255(3) Uani 1 1 d . . . . .
H25 H 0.317612 0.732653 0.739188 0.031 Uiso 1 1 calc R U . . .
C26 C 0.3170(2) 0.71921(16) 0.67055(4) 0.0218(3) Uani 1 1 d . . . . .
H26 H 0.222601 0.632042 0.666492 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
B3 H3A 1.123(16) . ?
B3 H3B 1.132(16) . ?
B3 C4 1.6156(18) . ?
B3 N8 1.5894(16) . ?
C4 C5 1.3553(17) . ?
C4 C21 1.4862(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.4504(17) . ?
C6 C7 1.4040(16) . ?
C6 C14 1.3860(16) . ?
C7 N8 1.3623(15) . ?
C7 C11 1.3858(17) . ?
N8 N9 1.3139(14) . ?
N9 N10 1.3514(14) . ?
N10 C11 1.3782(15) . ?
N10 C15 1.4305(15) . ?
C11 C12 1.4069(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3811(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.4165(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3877(18) . ?
C15 C20 1.3913(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3914(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.3882(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.4014(18) . ?
C21 C26 1.4016(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3917(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.3878(19) . ?
C26 H26 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
H3A B3 H3B 108.7(11) . . ?
C4 B3 H3A 113.6(8) . . ?
C4 B3 H3B 110.6(8) . . ?
N8 B3 H3A 108.5(8) . . ?
N8 B3 H3B 108.3(8) . . ?
N8 B3 C4 107.03(9) . . ?
C5 C4 B3 125.68(11) . . ?
C5 C4 C21 117.07(11) . . ?
C21 C4 B3 117.24(10) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.11(11) . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 117.56(11) . . ?
C14 C6 C5 128.43(11) . . ?
C14 C6 C7 114.01(11) . . ?
N8 C7 C6 127.04(11) . . ?
N8 C7 C11 108.11(10) . . ?
C11 C7 C6 124.85(11) . . ?
C7 N8 B3 121.53(10) . . ?
N9 N8 B3 127.82(9) . . ?
N9 N8 C7 110.65(10) . . ?
N8 N9 N10 106.14(9) . . ?
N9 N10 C11 111.63(10) . . ?
N9 N10 C15 120.03(10) . . ?
C11 N10 C15 128.09(10) . . ?
C7 C11 C12 120.66(11) . . ?
N10 C11 C7 103.47(10) . . ?
N10 C11 C12 135.84(11) . . ?
C11 C12 H12 122.3 . . ?
C13 C12 C11 115.31(11) . . ?
C13 C12 H12 122.3 . . ?
C12 C13 H13 118.3 . . ?
C12 C13 C14 123.35(11) . . ?
C14 C13 H13 118.3 . . ?
C6 C14 C13 121.79(11) . . ?
C6 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C16 C15 N10 119.34(11) . . ?
C16 C15 C20 121.84(12) . . ?
C20 C15 N10 118.78(11) . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.61(13) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.45(13) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.98(12) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.49(13) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 120.7 . . ?
C19 C20 C15 118.60(12) . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C4 120.93(11) . . ?
C22 C21 C26 118.11(12) . . ?
C26 C21 C4 120.95(11) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.57(13) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.57(13) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.31(12) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.60(13) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.80(12) . . ?
C25 C26 H26 119.6 . . ?

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
B3 C4 C5 C6 2.35(19) . . . . ?
B3 C4 C21 C22 -43.46(16) . . . . ?
B3 C4 C21 C26 137.74(12) . . . . ?
B3 N8 N9 N10 -179.13(11) . . . . ?
C4 B3 N8 C7 1.31(15) . . . . ?
C4 B3 N8 N9 -179.54(10) . . . . ?
C4 C5 C6 C7 -0.84(17) . . . . ?
C4 C5 C6 C14 179.20(12) . . . . ?
C4 C21 C22 C23 -176.54(12) . . . . ?
C4 C21 C26 C25 177.14(12) . . . . ?
C5 C4 C21 C22 137.43(13) . . . . ?
C5 C4 C21 C26 -41.37(17) . . . . ?
C5 C6 C7 N8 -0.23(18) . . . . ?
C5 C6 C7 C11 -179.31(11) . . . . ?
C5 C6 C14 C13 178.14(11) . . . . ?
C6 C7 N8 B3 -0.19(18) . . . . ?
C6 C7 N8 N9 -179.47(11) . . . . ?
C6 C7 C11 N10 179.54(11) . . . . ?
C6 C7 C11 C12 1.19(19) . . . . ?
C7 C6 C14 C13 -1.82(17) . . . . ?
C7 N8 N9 N10 0.09(13) . . . . ?
C7 C11 C12 C13 -1.77(17) . . . . ?
N8 B3 C4 C5 -2.44(17) . . . . ?
N8 B3 C4 C21 178.53(10) . . . . ?
N8 C7 C11 N10 0.31(13) . . . . ?
N8 C7 C11 C12 -178.03(11) . . . . ?
N8 N9 N10 C11 0.12(13) . . . . ?
N8 N9 N10 C15 174.84(10) . . . . ?
N9 N10 C11 C7 -0.27(13) . . . . ?
N9 N10 C11 C12 177.69(13) . . . . ?
N9 N10 C15 C16 -36.41(16) . . . . ?
N9 N10 C15 C20 145.92(12) . . . . ?
N10 C11 C12 C13 -179.46(13) . . . . ?
N10 C15 C16 C17 -176.48(12) . . . . ?
N10 C15 C20 C19 176.25(11) . . . . ?
C11 C7 N8 B3 179.02(10) . . . . ?
C11 C7 N8 N9 -0.26(14) . . . . ?
C11 N10 C15 C16 137.35(13) . . . . ?
C11 N10 C15 C20 -40.32(18) . . . . ?
C11 C12 C13 C14 0.62(18) . . . . ?
C12 C13 C14 C6 1.26(19) . . . . ?
C14 C6 C7 N8 179.73(12) . . . . ?
C14 C6 C7 C11 0.65(17) . . . . ?
C15 N10 C11 C7 -174.46(11) . . . . ?
C15 N10 C11 C12 3.5(2) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C16 C15 C20 C19 -1.35(19) . . . . ?
C16 C17 C18 C19 -1.5(2) . . . . ?
C17 C18 C19 C20 1.3(2) . . . . ?
C18 C19 C20 C15 0.1(2) . . . . ?
C20 C15 C16 C17 1.1(2) . . . . ?
C21 C4 C5 C6 -178.62(10) . . . . ?
C21 C22 C23 C24 -1.3(2) . . . . ?
C22 C21 C26 C25 -1.70(19) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C23 C24 C25 C26 0.9(2) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?
C26 C21 C22 C23 2.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_QT_N3_2
_database_code_depnum_ccdc_archive 'CCDC 2113569'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 B F3 N4'
_chemical_formula_sum            'C22 H14 B F3 N4'
_chemical_formula_weight         402.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8691(2)
_cell_length_b                   9.7159(2)
_cell_length_c                   11.5592(3)
_cell_angle_alpha                87.7510(10)
_cell_angle_beta                 85.0020(10)
_cell_angle_gamma                66.2210(10)
_cell_volume                     908.04(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8283
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.91
_cell_measurement_theta_min      3.84
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0660 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.9078.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14117
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.902
_diffrn_reflns_theta_min         3.839
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3345
_reflns_number_total             3798
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.3142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F30-C27 \\sim F33-C27 \\sim F29-C27 \\sim F32-C27 \\sim F28-C27 \\sim F31-C27
 with sigma of 0.001
 F31-F32 \\sim F31-F33 \\sim F28-F30 \\sim F28-F29 \\sim F33-F32 \\sim F30-F29
 with sigma of 0.01
3. Rigid body (RIGU) restrains
 C27, F28, F29, F30
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C27, F31, F32, F33
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(F28)=Sof(F29)=Sof(F30)=1-FVAR(1)
 Sof(F31)=Sof(F32)=Sof(F33)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.80977(17) 0.78864(13) 0.26782(10) 0.0291(3) Uani 1 1 d . . . . .
C2 C 0.73643(15) 0.74226(13) 0.33327(10) 0.0183(3) Uani 1 1 d . . . . .
B3 B 0.63641(17) 0.67527(15) 0.42379(12) 0.0160(3) Uani 1 1 d . . . . .
H3 H 0.513(2) 0.7694(18) 0.4515(14) 0.023(4) Uiso 1 1 d . . . . .
C4 C 0.74534(14) 0.59158(13) 0.53164(10) 0.0154(2) Uani 1 1 d . . . . .
C5 C 0.80356(14) 0.44068(13) 0.55011(10) 0.0162(2) Uani 1 1 d . . . . .
H5 H 0.866257 0.399381 0.615031 0.019 Uiso 1 1 calc R U . . .
C6 C 0.77352(14) 0.34002(13) 0.47428(10) 0.0162(2) Uani 1 1 d . . . . .
C7 C 0.67376(14) 0.40446(13) 0.38243(10) 0.0150(2) Uani 1 1 d . . . . .
N8 N 0.60205(12) 0.55342(11) 0.35689(8) 0.0151(2) Uani 1 1 d . . . . .
N9 N 0.51104(13) 0.57694(11) 0.26848(9) 0.0168(2) Uani 1 1 d . . . . .
N10 N 0.52544(13) 0.44076(11) 0.23546(9) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.62723(14) 0.32735(13) 0.30415(10) 0.0161(2) Uani 1 1 d . . . . .
C12 C 0.68453(15) 0.16953(13) 0.31135(11) 0.0179(2) Uani 1 1 d . . . . .
H12 H 0.656489 0.112506 0.258740 0.021 Uiso 1 1 calc R U . . .
C13 C 0.78449(15) 0.10387(13) 0.40055(11) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.826813 -0.002488 0.408273 0.023 Uiso 1 1 calc R U . . .
C14 C 0.82787(15) 0.18513(14) 0.48126(11) 0.0184(2) Uani 1 1 d . . . . .
H14 H 0.895584 0.132289 0.541330 0.022 Uiso 1 1 calc R U . . .
C15 C 0.43040(15) 0.43261(14) 0.14385(10) 0.0170(2) Uani 1 1 d . . . . .
C16 C 0.28192(16) 0.55299(14) 0.12696(11) 0.0195(3) Uani 1 1 d . . . . .
H16 H 0.244438 0.639624 0.174710 0.023 Uiso 1 1 calc R U . . .
C17 C 0.18927(16) 0.54436(15) 0.03895(11) 0.0224(3) Uani 1 1 d . . . . .
H17 H 0.088134 0.626457 0.025512 0.027 Uiso 1 1 calc R U . . .
C18 C 0.24310(17) 0.41674(16) -0.02965(11) 0.0236(3) Uani 1 1 d . . . . .
H18 H 0.177921 0.410954 -0.088768 0.028 Uiso 1 1 calc R U . . .
C19 C 0.39226(17) 0.29765(15) -0.01173(11) 0.0232(3) Uani 1 1 d . . . . .
H19 H 0.428850 0.210514 -0.058855 0.028 Uiso 1 1 calc R U . . .
C20 C 0.48863(16) 0.30486(14) 0.07470(11) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.591821 0.224405 0.086216 0.025 Uiso 1 1 calc R U . . .
C21 C 0.78278(14) 0.68655(13) 0.61280(10) 0.0152(2) Uani 1 1 d . . . . .
C22 C 0.69387(16) 0.84347(14) 0.61538(11) 0.0194(3) Uani 1 1 d . . . . .
H22 H 0.610739 0.889441 0.562880 0.023 Uiso 1 1 calc R U . . .
C23 C 0.72488(16) 0.93275(14) 0.69295(11) 0.0203(3) Uani 1 1 d . . . . .
H23 H 0.662410 1.038439 0.693711 0.024 Uiso 1 1 calc R U . . .
C24 C 0.84741(15) 0.86742(14) 0.76953(11) 0.0185(3) Uani 1 1 d . . . . .
C25 C 0.93884(15) 0.71272(14) 0.76739(10) 0.0183(3) Uani 1 1 d . . . . .
H25 H 1.023189 0.667645 0.819139 0.022 Uiso 1 1 calc R U . . .
C26 C 0.90721(15) 0.62444(13) 0.69012(10) 0.0166(2) Uani 1 1 d . . . . .
H26 H 0.971274 0.519023 0.689274 0.020 Uiso 1 1 calc R U . . .
C27 C 0.87776(12) 0.96313(12) 0.85448(10) 0.0251(3) Uani 1 1 d D . . . .
F28 F 1.0258(6) 0.8958(10) 0.8974(7) 0.0269(9) Uani 0.58(2) 1 d D . P A 1
F29 F 0.8688(13) 1.0956(7) 0.8105(8) 0.0571(14) Uani 0.58(2) 1 d D . P A 1
F30 F 0.7663(9) 0.9953(12) 0.9463(6) 0.0559(14) Uani 0.58(2) 1 d D . P A 1
F31 F 1.0092(8) 0.8890(14) 0.9150(10) 0.0317(15) Uani 0.42(2) 1 d D . P A 2
F32 F 0.9046(10) 1.0767(5) 0.8006(7) 0.0301(11) Uani 0.42(2) 1 d D . P A 2
F33 F 0.7498(11) 1.0261(10) 0.9332(8) 0.0406(12) Uani 0.42(2) 1 d D . P A 2


_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 C2 1.1499(18) . ?
C2 B3 1.5987(18) . ?
B3 H3 1.134(16) . ?
B3 C4 1.6266(17) . ?
B3 N8 1.5799(16) . ?
C4 C5 1.3586(16) . ?
C4 C21 1.4869(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.4539(17) . ?
C6 C7 1.4024(17) . ?
C6 C14 1.3841(16) . ?
C7 N8 1.3577(15) . ?
C7 C11 1.3849(17) . ?
N8 N9 1.3133(14) . ?
N9 N10 1.3444(14) . ?
N10 C11 1.3833(15) . ?
N10 C15 1.4332(15) . ?
C11 C12 1.4091(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3812(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.4167(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3875(18) . ?
C15 C20 1.3911(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3876(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3884(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.3880(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3915(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.4061(16) . ?
C21 C26 1.4048(17) . ?
C22 H22 0.9500 . ?
C22 C23 1.3887(18) . ?
C23 H23 0.9500 . ?
C23 C24 1.3909(18) . ?
C24 C25 1.3906(17) . ?
C24 C27 1.4903(18) . ?
C25 H25 0.9500 . ?
C25 C26 1.3820(18) . ?
C26 H26 0.9500 . ?
C27 F28 1.3391(12) . ?
C27 F29 1.3391(12) . ?
C27 F30 1.3399(12) . ?
C27 F31 1.3392(12) . ?
C27 F32 1.3399(12) . ?
C27 F33 1.3393(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 B3 179.14(13) . . ?
C2 B3 H3 108.4(8) . . ?
C2 B3 C4 111.20(10) . . ?
C4 B3 H3 113.7(8) . . ?
N8 B3 C2 107.00(9) . . ?
N8 B3 H3 108.5(8) . . ?
N8 B3 C4 107.87(9) . . ?
C5 C4 B3 123.27(11) . . ?
C5 C4 C21 119.12(11) . . ?
C21 C4 B3 117.61(10) . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.49(11) . . ?
C6 C5 H5 118.8 . . ?
C7 C6 C5 117.68(11) . . ?
C14 C6 C5 128.56(11) . . ?
C14 C6 C7 113.75(11) . . ?
N8 C7 C6 126.01(11) . . ?
N8 C7 C11 108.14(10) . . ?
C11 C7 C6 125.83(11) . . ?
C7 N8 B3 122.26(10) . . ?
N9 N8 B3 126.87(9) . . ?
N9 N8 C7 110.79(10) . . ?
N8 N9 N10 106.19(9) . . ?
N9 N10 C11 111.64(10) . . ?
N9 N10 C15 118.50(10) . . ?
C11 N10 C15 129.73(10) . . ?
C7 C11 C12 119.95(11) . . ?
N10 C11 C7 103.24(10) . . ?
N10 C11 C12 136.80(11) . . ?
C11 C12 H12 122.5 . . ?
C13 C12 C11 115.04(11) . . ?
C13 C12 H12 122.5 . . ?
C12 C13 H13 117.9 . . ?
C12 C13 C14 124.13(11) . . ?
C14 C13 H13 117.9 . . ?
C6 C14 C13 121.28(11) . . ?
C6 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 N10 118.75(11) . . ?
C16 C15 C20 121.81(12) . . ?
C20 C15 N10 119.44(11) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.69(12) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.56(12) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.92(12) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.52(12) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 118.47(12) . . ?
C15 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C22 C21 C4 121.02(11) . . ?
C26 C21 C4 121.91(11) . . ?
C26 C21 C22 117.07(11) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.47(11) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 119.99(11) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C27 119.85(10) . . ?
C25 C24 C23 119.62(11) . . ?
C25 C24 C27 120.53(11) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.12(11) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.1 . . ?
C25 C26 C21 121.71(11) . . ?
C25 C26 H26 119.1 . . ?
F28 C27 C24 112.7(4) . . ?
F28 C27 F29 106.8(3) . . ?
F28 C27 F30 105.9(3) . . ?
F29 C27 C24 113.6(4) . . ?
F29 C27 F30 106.1(3) . . ?
F30 C27 C24 111.1(4) . . ?
F31 C27 C24 113.8(6) . . ?
F31 C27 F32 106.3(4) . . ?
F31 C27 F33 106.0(4) . . ?
F32 C27 C24 110.9(4) . . ?
F33 C27 C24 113.0(6) . . ?
F33 C27 F32 106.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 B3 C4 C5 -112.30(13) . . . . ?
C2 B3 C4 C21 67.31(13) . . . . ?
C2 B3 N8 C7 112.33(11) . . . . ?
C2 B3 N8 N9 -64.20(14) . . . . ?
B3 C4 C5 C6 0.12(18) . . . . ?
B3 C4 C21 C22 16.25(16) . . . . ?
B3 C4 C21 C26 -163.93(11) . . . . ?
B3 N8 N9 N10 176.23(10) . . . . ?
C4 B3 N8 C7 -7.39(15) . . . . ?
C4 B3 N8 N9 176.07(10) . . . . ?
C4 C5 C6 C7 -3.11(17) . . . . ?
C4 C5 C6 C14 178.48(12) . . . . ?
C4 C21 C22 C23 178.27(11) . . . . ?
C4 C21 C26 C25 -178.37(11) . . . . ?
C5 C4 C21 C22 -164.12(11) . . . . ?
C5 C4 C21 C26 15.70(17) . . . . ?
C5 C6 C7 N8 0.22(18) . . . . ?
C5 C6 C7 C11 -177.68(11) . . . . ?
C5 C6 C14 C13 178.88(11) . . . . ?
C6 C7 N8 B3 5.59(18) . . . . ?
C6 C7 N8 N9 -177.38(11) . . . . ?
C6 C7 C11 N10 177.57(11) . . . . ?
C6 C7 C11 C12 -1.62(19) . . . . ?
C7 C6 C14 C13 0.43(17) . . . . ?
C7 N8 N9 N10 -0.63(12) . . . . ?
C7 C11 C12 C13 0.77(17) . . . . ?
N8 B3 C4 C5 4.73(15) . . . . ?
N8 B3 C4 C21 -175.66(9) . . . . ?
N8 C7 C11 N10 -0.65(12) . . . . ?
N8 C7 C11 C12 -179.83(10) . . . . ?
N8 N9 N10 C11 0.20(13) . . . . ?
N8 N9 N10 C15 176.38(10) . . . . ?
N9 N10 C11 C7 0.28(13) . . . . ?
N9 N10 C11 C12 179.25(13) . . . . ?
N9 N10 C15 C16 -27.72(15) . . . . ?
N9 N10 C15 C20 152.46(11) . . . . ?
N10 C11 C12 C13 -178.07(13) . . . . ?
N10 C15 C16 C17 -179.39(11) . . . . ?
N10 C15 C20 C19 178.31(11) . . . . ?
C11 C7 N8 B3 -176.20(10) . . . . ?
C11 C7 N8 N9 0.83(13) . . . . ?
C11 N10 C15 C16 147.66(12) . . . . ?
C11 N10 C15 C20 -32.16(18) . . . . ?
C11 C12 C13 C14 0.56(18) . . . . ?
C12 C13 C14 C6 -1.21(19) . . . . ?
C14 C6 C7 N8 178.86(11) . . . . ?
C14 C6 C7 C11 0.96(18) . . . . ?
C15 N10 C11 C7 -175.35(11) . . . . ?
C15 N10 C11 C12 3.6(2) . . . . ?
C15 C16 C17 C18 0.94(19) . . . . ?
C16 C15 C20 C19 -1.50(19) . . . . ?
C16 C17 C18 C19 -1.19(19) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C15 1.25(19) . . . . ?
C20 C15 C16 C17 0.42(18) . . . . ?
C21 C4 C5 C6 -179.49(10) . . . . ?
C21 C22 C23 C24 0.70(19) . . . . ?
C22 C21 C26 C25 1.46(18) . . . . ?
C22 C23 C24 C25 0.34(19) . . . . ?
C22 C23 C24 C27 -178.61(11) . . . . ?
C23 C24 C25 C26 -0.45(18) . . . . ?
C23 C24 C27 F28 -161.5(5) . . . . ?
C23 C24 C27 F29 -39.9(5) . . . . ?
C23 C24 C27 F30 79.7(5) . . . . ?
C23 C24 C27 F31 -173.8(5) . . . . ?
C23 C24 C27 F32 -53.9(4) . . . . ?
C23 C24 C27 F33 65.3(5) . . . . ?
C24 C25 C26 C21 -0.48(18) . . . . ?
C25 C24 C27 F28 19.5(5) . . . . ?
C25 C24 C27 F29 141.2(5) . . . . ?
C25 C24 C27 F30 -99.2(5) . . . . ?
C25 C24 C27 F31 7.3(5) . . . . ?
C25 C24 C27 F32 127.1(4) . . . . ?
C25 C24 C27 F33 -113.7(5) . . . . ?
C26 C21 C22 C23 -1.56(18) . . . . ?
C27 C24 C25 C26 178.50(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 2114265'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;University of South Florida
United States of America
;
_audit_update_record             
;
2021-10-06 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_audit_creation_date             2021-10-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H30 B2 N8 O2'
_chemical_formula_sum            'C34 H30 B2 N8 O2'
_chemical_formula_weight         604.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.0807(2)
_cell_length_b                   9.70710(10)
_cell_length_c                   19.4956(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2853.96(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9819
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.68
_cell_measurement_theta_min      4.54
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0897 before and 0.0792 after correction.
The Ratio of minimum to maximum transmission is 0.9148.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.157
_diffrn_reflns_theta_min         4.536
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2588
_reflns_number_total             3101
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+1.7685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0879
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.68162(8) 0.75747(13) 0.34340(6) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.66088(9) 0.70097(14) 0.39272(7) 0.0151(3) Uani 1 1 d . . . . .
B3 B 0.63654(10) 0.61682(15) 0.46114(7) 0.0145(3) Uani 1 1 d . . . . .
H3 H 0.6961(11) 0.5460(17) 0.4744(8) 0.012(4) Uiso 1 1 d . . . . .
C4 C 0.54359(8) 0.52745(13) 0.45462(6) 0.0130(3) Uani 1 1 d . . . . .
C5 C 0.45653(8) 0.58910(13) 0.48649(6) 0.0130(3) Uani 1 1 d . . . . .
H5 H 0.4031(11) 0.5767(17) 0.4561(9) 0.016 Uiso 1 1 d . U . . .
C6 C 0.45998(8) 0.73339(13) 0.51245(6) 0.0136(3) Uani 1 1 d . . . . .
C7 C 0.54259(8) 0.78234(13) 0.53415(6) 0.0132(3) Uani 1 1 d . . . . .
N8 N 0.62379(7) 0.72883(11) 0.51964(5) 0.0139(2) Uani 1 1 d . . . . .
N9 N 0.68660(7) 0.80226(11) 0.54962(6) 0.0148(2) Uani 1 1 d . . . . .
N10 N 0.64543(7) 0.90307(11) 0.58342(5) 0.0142(2) Uani 1 1 d . . . . .
C11 C 0.55517(9) 0.89732(13) 0.57503(6) 0.0135(3) Uani 1 1 d . . . . .
C12 C 0.48276(9) 0.97967(13) 0.59485(7) 0.0157(3) Uani 1 1 d . . . . .
H12 H 0.489300 1.057760 0.623784 0.019 Uiso 1 1 calc R U . . .
C13 C 0.40161(9) 0.93890(14) 0.56928(7) 0.0164(3) Uani 1 1 d . . . . .
H13 H 0.351166 0.994079 0.579130 0.020 Uiso 1 1 calc R U . . .
C14 C 0.38980(9) 0.81848(14) 0.52897(7) 0.0150(3) Uani 1 1 d . . . . .
H14 H 0.332121 0.795874 0.512939 0.018 Uiso 1 1 calc R U . . .
C15 C 0.69603(9) 0.99532(14) 0.62825(7) 0.0171(3) Uani 1 1 d . . . . .
H15A H 0.670651 1.089261 0.625918 0.021 Uiso 1 1 calc R U . . .
H15B H 0.758283 0.999949 0.612298 0.021 Uiso 1 1 calc R U . . .
C16 C 0.69366(9) 0.94453(15) 0.70169(7) 0.0186(3) Uani 1 1 d . . . . .
H16A H 0.723951 1.011223 0.732138 0.022 Uiso 1 1 calc R U . . .
H16B H 0.631485 0.934799 0.717249 0.022 Uiso 1 1 calc R U . . .
O17 O 0.73722(7) 0.81522(11) 0.70438(5) 0.0234(2) Uani 1 1 d . . . . .
H17 H 0.7225(17) 0.777(3) 0.7455(14) 0.056(7) Uiso 1 1 d . . . . .
C18 C 0.53158(9) 0.47145(13) 0.38211(7) 0.0143(3) Uani 1 1 d . . . . .
C19 C 0.59666(9) 0.38423(14) 0.35458(7) 0.0158(3) Uani 1 1 d . . . . .
H19 H 0.651723 0.374564 0.377753 0.019 Uiso 1 1 calc R U . . .
C20 C 0.58229(9) 0.31168(14) 0.29415(7) 0.0176(3) Uani 1 1 d . . . . .
H20 H 0.625956 0.249114 0.277930 0.021 Uiso 1 1 calc R U . . .
C21 C 0.50421(10) 0.33034(15) 0.25734(7) 0.0194(3) Uani 1 1 d . . . . .
H21 H 0.492788 0.277344 0.217337 0.023 Uiso 1 1 calc R U . . .
C22 C 0.44330(10) 0.42726(15) 0.27978(7) 0.0199(3) Uani 1 1 d . . . . .
H22 H 0.392258 0.446680 0.252901 0.024 Uiso 1 1 calc R U . . .
C23 C 0.45659(9) 0.49646(14) 0.34168(7) 0.0169(3) Uani 1 1 d . . . . .
H23 H 0.413901 0.561828 0.356665 0.020 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 C2 1.1502(19) . ?
C2 B3 1.6066(19) . ?
B3 H3 1.160(17) . ?
B3 C4 1.6534(19) . ?
B3 N8 1.5874(18) . ?
C4 C5 1.5710(17) . ?
C4 C5 1.6120(17) 5_666 ?
C4 C18 1.5253(17) . ?
C5 H5 1.007(17) . ?
C5 C6 1.4903(18) . ?
C6 C7 1.3989(18) . ?
C6 C14 1.3805(18) . ?
C7 N8 1.3599(17) . ?
C7 C11 1.3846(18) . ?
N8 N9 1.3216(15) . ?
N9 N10 1.3332(16) . ?
N10 C11 1.3721(17) . ?
N10 C15 1.4656(16) . ?
C11 C12 1.4074(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3794(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.4198(19) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5147(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 O17 1.4176(17) . ?
O17 H17 0.91(3) . ?
C18 C19 1.4028(19) . ?
C18 C23 1.3997(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3896(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3956(19) . ?
C23 H23 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
N1 C2 B3 176.91(14) . . ?
C2 B3 H3 108.0(8) . . ?
C2 B3 C4 113.37(11) . . ?
C4 B3 H3 111.3(8) . . ?
N8 B3 C2 106.02(11) . . ?
N8 B3 H3 109.9(8) . . ?
N8 B3 C4 108.18(10) . . ?
C5 C4 B3 118.57(10) . . ?
C5 C4 B3 108.32(10) 5_666 . ?
C5 C4 C5 89.12(9) . 5_666 ?
C18 C4 B3 111.04(10) . . ?
C18 C4 C5 114.20(10) . 5_666 ?
C18 C4 C5 113.77(10) . . ?
C4 C5 C4 90.88(9) . 5_666 ?
C4 C5 H5 109.5(10) 5_666 . ?
C4 C5 H5 112.9(10) . . ?
C6 C5 C4 117.59(11) . . ?
C6 C5 C4 114.69(10) . 5_666 ?
C6 C5 H5 109.9(10) . . ?
C7 C6 C5 116.94(11) . . ?
C14 C6 C5 127.93(12) . . ?
C14 C6 C7 114.14(12) . . ?
N8 C7 C6 127.54(12) . . ?
N8 C7 C11 107.72(11) . . ?
C11 C7 C6 124.74(12) . . ?
C7 N8 B3 121.34(11) . . ?
N9 N8 B3 126.89(10) . . ?
N9 N8 C7 110.32(11) . . ?
N8 N9 N10 106.31(10) . . ?
N9 N10 C11 111.91(11) . . ?
N9 N10 C15 120.06(11) . . ?
C11 N10 C15 127.77(11) . . ?
C7 C11 C12 120.63(12) . . ?
N10 C11 C7 103.73(11) . . ?
N10 C11 C12 135.55(12) . . ?
C11 C12 H12 122.4 . . ?
C13 C12 C11 115.23(12) . . ?
C13 C12 H12 122.4 . . ?
C12 C13 H13 118.4 . . ?
C12 C13 C14 123.20(12) . . ?
C14 C13 H13 118.4 . . ?
C6 C14 C13 121.70(12) . . ?
C6 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
N10 C15 H15A 109.5 . . ?
N10 C15 H15B 109.5 . . ?
N10 C15 C16 110.64(11) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16A 110.1 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
O17 C16 C15 108.19(11) . . ?
O17 C16 H16A 110.1 . . ?
O17 C16 H16B 110.1 . . ?
C16 O17 H17 106.3(16) . . ?
C19 C18 C4 119.11(12) . . ?
C23 C18 C4 123.78(12) . . ?
C23 C18 C19 117.03(12) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.41(13) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.23(13) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.13(13) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.30(13) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.30(13) . . ?
C22 C23 H23 119.3 . . ?

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
C2 B3 C4 C5 -99.71(13) . . . . ?
C2 B3 C4 C5 160.97(11) . . . 5_666 ?
C2 B3 C4 C18 34.81(15) . . . . ?
C2 B3 N8 C7 92.84(13) . . . . ?
C2 B3 N8 N9 -72.08(15) . . . . ?
B3 C4 C5 C4 -110.47(12) . . . 5_666 ?
B3 C4 C5 C6 8.17(17) . . . . ?
B3 C4 C18 C19 58.86(15) . . . . ?
B3 C4 C18 C23 -124.35(13) . . . . ?
B3 N8 N9 N10 166.30(11) . . . . ?
C4 B3 N8 C7 -29.07(16) . . . . ?
C4 B3 N8 N9 166.01(11) . . . . ?
C4 C5 C6 C7 -26.79(17) . . . . ?
C4 C5 C6 C7 78.23(15) 5_666 . . . ?
C4 C5 C6 C14 -89.70(16) 5_666 . . . ?
C4 C5 C6 C14 165.28(13) . . . . ?
C4 C18 C19 C20 168.76(12) . . . . ?
C4 C18 C23 C22 -170.82(12) . . . . ?
C5 C4 C5 C4 -0.002(0) 5_666 . . 5_666 ?
C5 C4 C5 C6 118.64(13) 5_666 . . . ?
C5 C4 C18 C19 -164.31(11) . . . . ?
C5 C4 C18 C19 -63.97(15) 5_666 . . . ?
C5 C4 C18 C23 112.83(14) 5_666 . . . ?
C5 C4 C18 C23 12.48(18) . . . . ?
C5 C6 C7 N8 17.5(2) . . . . ?
C5 C6 C7 C11 -162.81(12) . . . . ?
C5 C6 C14 C13 163.43(13) . . . . ?
C6 C7 N8 B3 13.3(2) . . . . ?
C6 C7 N8 N9 -179.47(13) . . . . ?
C6 C7 C11 N10 179.06(12) . . . . ?
C6 C7 C11 C12 -3.7(2) . . . . ?
C7 C6 C14 C13 -4.77(18) . . . . ?
C7 N8 N9 N10 0.01(14) . . . . ?
C7 C11 C12 C13 -1.59(18) . . . . ?
N8 B3 C4 C5 17.57(15) . . . . ?
N8 B3 C4 C5 -81.76(12) . . . 5_666 ?
N8 B3 C4 C18 152.09(10) . . . . ?
N8 C7 C11 N10 -1.16(13) . . . . ?
N8 C7 C11 C12 176.06(11) . . . . ?
N8 N9 N10 C11 -0.80(14) . . . . ?
N8 N9 N10 C15 173.71(11) . . . . ?
N9 N10 C11 C7 1.22(14) . . . . ?
N9 N10 C11 C12 -175.36(14) . . . . ?
N9 N10 C15 C16 -94.45(14) . . . . ?
N10 C11 C12 C13 174.55(14) . . . . ?
N10 C15 C16 O17 64.14(14) . . . . ?
C11 C7 N8 B3 -166.43(11) . . . . ?
C11 C7 N8 N9 0.75(14) . . . . ?
C11 N10 C15 C16 79.10(16) . . . . ?
C11 C12 C13 C14 3.42(19) . . . . ?
C12 C13 C14 C6 -0.1(2) . . . . ?
C14 C6 C7 N8 -172.96(12) . . . . ?
C14 C6 C7 C11 6.78(19) . . . . ?
C15 N10 C11 C7 -172.76(12) . . . . ?
C15 N10 C11 C12 10.7(2) . . . . ?
C18 C4 C5 C4 116.18(12) . . . 5_666 ?
C18 C4 C5 C6 -125.18(12) . . . . ?
C18 C19 C20 C21 3.7(2) . . . . ?
C19 C18 C23 C22 6.04(19) . . . . ?
C19 C20 C21 C22 3.4(2) . . . . ?
C20 C21 C22 C23 -5.5(2) . . . . ?
C21 C22 C23 C18 0.7(2) . . . . ?
C23 C18 C19 C20 -8.25(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
