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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_TEST_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2336090'
loop_
_audit_author_name
_audit_author_address
'RETWIK PARUI'
;INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI
India
;
_audit_update_record             
;
2024-02-28 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 B N3'
_chemical_formula_weight         287.16

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

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

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

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

_cell_length_a                   13.9391(9)
_cell_length_b                   11.2303(7)
_cell_length_c                   20.3661(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.938(2)
_cell_angle_gamma                90
_cell_volume                     3080.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9512
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73129
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.041
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5403
_reflns_number_gt                3963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.3745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5403
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.2005
_refine_ls_wR_factor_gt          0.1597
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.37406(10) 0.86717(13) 0.19868(7) 0.0521(4) Uani 1 1 d . . . . .
H001 H 0.418768 0.919362 0.197575 0.062 Uiso 1 1 calc R U . . .
N002 N 0.32566(10) 0.68379(13) 0.24095(7) 0.0522(4) Uani 1 1 d . . . . .
H002 H 0.338951 0.623473 0.267783 0.063 Uiso 1 1 calc R U . . .
N003 N 0.67206(11) 0.53469(14) 0.24713(8) 0.0578(4) Uani 1 1 d . . . . .
H003 H 0.659433 0.586101 0.214737 0.069 Uiso 1 1 calc R U . . .
N004 N 0.78865(11) 0.76157(16) 0.43410(8) 0.0646(5) Uani 1 1 d . . . . .
N005 N 0.62161(10) 0.37415(15) 0.30740(8) 0.0647(5) Uani 1 1 d . . . . .
H005 H 0.576958 0.325052 0.312877 0.078 Uiso 1 1 calc R U . . .
N006 N 0.20639(12) 0.42997(16) 0.06246(8) 0.0696(5) Uani 1 1 d . . . . .
C1 C 0.20674(12) 0.79617(16) 0.15649(8) 0.0480(4) Uani 1 1 d . . . . .
C008 C 0.50688(12) 0.75960(16) 0.29197(8) 0.0487(4) Uani 1 1 d . . . . .
C009 C 0.69764(12) 0.75953(16) 0.38753(8) 0.0518(4) Uani 1 1 d . . . . .
C00A C 0.10939(13) 0.80944(17) 0.11362(9) 0.0557(5) Uani 1 1 d . . . . .
C00B C 0.27901(12) 0.88527(16) 0.15724(8) 0.0503(4) Uani 1 1 d . . . . .
C00C C 0.62202(12) 0.68166(17) 0.39406(9) 0.0551(5) Uani 1 1 d . . . . .
H00C H 0.633738 0.628428 0.430239 0.066 Uiso 1 1 calc R U . . .
C00D C 0.23026(12) 0.69293(15) 0.19834(8) 0.0492(4) Uani 1 1 d . . . . .
C00E C 0.49039(12) 0.45448(16) 0.20248(9) 0.0521(4) Uani 1 1 d . . . . .
C00F C 0.53066(12) 0.68294(16) 0.34764(9) 0.0533(4) Uani 1 1 d . . . . .
H00F H 0.482384 0.629984 0.353728 0.064 Uiso 1 1 calc R U . . .
C00G C 0.78888(13) 0.44853(18) 0.34396(10) 0.0584(5) Uani 1 1 d . . . . .
C00H C 0.76726(13) 0.53344(17) 0.29078(10) 0.0573(5) Uani 1 1 d . . . . .
C00I C 0.29823(13) 0.43853(17) 0.10800(9) 0.0555(5) Uani 1 1 d . . . . .
C00J C 0.46276(13) 0.52500(18) 0.14447(10) 0.0611(5) Uani 1 1 d . . . . .
H00J H 0.508635 0.579191 0.136074 0.073 Uiso 1 1 calc R U . . .
C00K C 0.03851(13) 0.7191(2) 0.11315(10) 0.0666(5) Uani 1 1 d . . . . .
H00K H -0.025258 0.725967 0.084797 0.080 Uiso 1 1 calc R U . . .
C00L C 0.15860(13) 0.60858(18) 0.19672(10) 0.0618(5) Uani 1 1 d . . . . .
H00L H 0.173574 0.541615 0.224338 0.074 Uiso 1 1 calc R U . . .
C00M C 0.41652(13) 0.37628(18) 0.21089(10) 0.0607(5) Uani 1 1 d . . . . .
H00M H 0.430598 0.327151 0.248940 0.073 Uiso 1 1 calc R U . . .
C00N C 0.25308(14) 0.98636(17) 0.11839(10) 0.0617(5) Uani 1 1 d . . . . .
H00N H 0.299502 1.046522 0.120067 0.074 Uiso 1 1 calc R U . . .
C00O C 0.37089(14) 0.51847(19) 0.09893(10) 0.0640(5) Uani 1 1 d . . . . .
H00O H 0.356685 0.568346 0.061209 0.077 Uiso 1 1 calc R U . . .
C00P C 0.58396(13) 0.83445(17) 0.28589(9) 0.0589(5) Uani 1 1 d . . . . .
H00P H 0.572432 0.886842 0.249318 0.071 Uiso 1 1 calc R U . . .
C00Q C 0.67625(13) 0.83476(18) 0.33126(9) 0.0598(5) Uani 1 1 d . . . . .
H00Q H 0.725064 0.885996 0.324217 0.072 Uiso 1 1 calc R U . . .
C00R C 0.32435(14) 0.36777(18) 0.16624(10) 0.0625(5) Uani 1 1 d . . . . .
H00R H 0.278485 0.313881 0.174951 0.075 Uiso 1 1 calc R U . . .
C00S C 0.08708(15) 0.9130(2) 0.07355(10) 0.0692(6) Uani 1 1 d . . . . .
H00S H 0.023892 0.922983 0.044823 0.083 Uiso 1 1 calc R U . . .
C00T C 0.06334(14) 0.6223(2) 0.15396(11) 0.0697(6) Uani 1 1 d . . . . .
H00T H 0.015838 0.563936 0.153431 0.084 Uiso 1 1 calc R U . . .
C00U C 0.95805(15) 0.5246(2) 0.37942(13) 0.0789(7) Uani 1 1 d . . . . .
H00U H 1.021604 0.522932 0.408467 0.095 Uiso 1 1 calc R U . . .
C00V C 0.71512(13) 0.3674(2) 0.35262(11) 0.0666(5) Uani 1 1 d . . . . .
C00W C 0.80823(14) 0.6845(2) 0.49271(10) 0.0688(6) Uani 1 1 d . . . . .
H00A H 0.756080 0.692856 0.515316 0.103 Uiso 1 1 calc R U . . .
H00B H 0.870491 0.706035 0.523341 0.103 Uiso 1 1 calc R U . . .
H00D H 0.811145 0.603401 0.478492 0.103 Uiso 1 1 calc R U . . .
B1 B 0.40216(14) 0.76765(18) 0.24287(10) 0.0477(5) Uani 1 1 d . . . . .
C00Y C 0.86752(14) 0.8359(2) 0.42372(11) 0.0686(6) Uani 1 1 d . . . . .
H00E H 0.880312 0.816987 0.380801 0.103 Uiso 1 1 calc R U . . .
H00G H 0.926473 0.822414 0.459545 0.103 Uiso 1 1 calc R U . . .
H00H H 0.848381 0.918032 0.423898 0.103 Uiso 1 1 calc R U . . .
C00Z C 0.15705(16) 0.99839(19) 0.07651(10) 0.0714(6) Uani 1 1 d . . . . .
H00Z H 0.140612 1.066487 0.050003 0.086 Uiso 1 1 calc R U . . .
C010 C 0.93558(16) 0.6049(2) 0.32785(14) 0.0823(7) Uani 1 1 d . . . . .
H010 H 0.984363 0.657329 0.322006 0.099 Uiso 1 1 calc R U . . .
C011 C 0.84047(15) 0.61055(19) 0.28321(12) 0.0725(6) Uani 1 1 d . . . . .
H011 H 0.826807 0.666537 0.248389 0.087 Uiso 1 1 calc R U . . .
C012 C 0.88562(14) 0.4439(2) 0.38913(11) 0.0706(6) Uani 1 1 d . . . . .
B2 B 0.59477(15) 0.45647(19) 0.25281(11) 0.0527(5) Uani 1 1 d . . . . .
C014 C 0.17517(16) 0.5152(2) 0.00862(11) 0.0815(7) Uani 1 1 d . . . . .
H01A H 0.177742 0.593781 0.027569 0.122 Uiso 1 1 calc R U . . .
H01B H 0.108417 0.497747 -0.016586 0.122 Uiso 1 1 calc R U . . .
H01C H 0.218485 0.511094 -0.021102 0.122 Uiso 1 1 calc R U . . .
C015 C 0.13152(16) 0.3526(2) 0.07583(12) 0.0817(7) Uani 1 1 d . . . . .
H01D H 0.154848 0.271808 0.078902 0.123 Uiso 1 1 calc R U . . .
H01E H 0.072048 0.359107 0.039603 0.123 Uiso 1 1 calc R U . . .
H01F H 0.117639 0.375059 0.117923 0.123 Uiso 1 1 calc R U . . .
C016 C 0.90443(17) 0.3599(3) 0.44198(13) 0.0957(8) Uani 1 1 d . . . . .
H016 H 0.966708 0.357366 0.472641 0.115 Uiso 1 1 calc R U . . .
C017 C 0.73839(16) 0.2851(3) 0.40417(14) 0.1012(9) Uani 1 1 d . . . . .
H017 H 0.690647 0.230563 0.409325 0.121 Uiso 1 1 calc R U . . .
C018 C 0.83304(17) 0.2824(3) 0.44897(15) 0.1152(11) Uani 1 1 d . . . . .
H018 H 0.847264 0.226825 0.483993 0.138 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
N001 C00B 1.390(2) . ?
N001 B1 1.425(2) . ?
N002 C00D 1.392(2) . ?
N002 B1 1.416(2) . ?
N003 C00H 1.394(2) . ?
N003 B2 1.418(3) . ?
N004 C009 1.374(2) . ?
N004 C00Y 1.439(2) . ?
N004 C00W 1.442(2) . ?
N005 C00V 1.391(2) . ?
N005 B2 1.420(3) . ?
N006 C00I 1.377(2) . ?
N006 C014 1.436(3) . ?
N006 C015 1.437(3) . ?
C1 C00B 1.417(2) . ?
C1 C00A 1.420(2) . ?
C1 C00D 1.426(2) . ?
C008 C00F 1.394(2) . ?
C008 C00P 1.395(2) . ?
C008 B1 1.545(2) . ?
C009 C00Q 1.393(2) . ?
C009 C00C 1.402(2) . ?
C00A C00S 1.409(3) . ?
C00A C00K 1.415(3) . ?
C00B C00N 1.378(3) . ?
C00C C00F 1.377(2) . ?
C00D C00L 1.371(2) . ?
C00E C00J 1.392(2) . ?
C00E C00M 1.397(3) . ?
C00E B2 1.549(3) . ?
C00G C00H 1.416(3) . ?
C00G C00V 1.418(3) . ?
C00G C012 1.424(2) . ?
C00H C011 1.377(3) . ?
C00I C00R 1.396(3) . ?
C00I C00O 1.401(3) . ?
C00J C00O 1.376(2) . ?
C00K C00T 1.357(3) . ?
C00L C00T 1.396(3) . ?
C00M C00R 1.373(2) . ?
C00N C00Z 1.396(2) . ?
C00P C00Q 1.377(2) . ?
C00S C00Z 1.358(3) . ?
C00U C010 1.358(3) . ?
C00U C012 1.408(3) . ?
C00V C017 1.374(3) . ?
C010 C011 1.402(3) . ?
C012 C016 1.404(3) . ?
C016 C018 1.357(4) . ?
C017 C018 1.398(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B N001 B1 124.18(15) . . ?
C00D N002 B1 124.06(15) . . ?
C00H N003 B2 124.07(16) . . ?
C009 N004 C00Y 120.84(15) . . ?
C009 N004 C00W 120.34(16) . . ?
C00Y N004 C00W 118.75(15) . . ?
C00V N005 B2 124.52(17) . . ?
C00I N006 C014 120.92(17) . . ?
C00I N006 C015 120.60(16) . . ?
C014 N006 C015 117.13(16) . . ?
C00B C1 C00A 119.78(16) . . ?
C00B C1 C00D 120.95(15) . . ?
C00A C1 C00D 119.27(16) . . ?
C00F C008 C00P 114.67(15) . . ?
C00F C008 B1 123.34(15) . . ?
C00P C008 B1 121.89(15) . . ?
N004 C009 C00Q 121.43(16) . . ?
N004 C009 C00C 121.85(15) . . ?
C00Q C009 C00C 116.72(16) . . ?
C00S C00A C00K 122.60(17) . . ?
C00S C00A C1 118.44(18) . . ?
C00K C00A C1 118.95(17) . . ?
C00N C00B N001 122.48(16) . . ?
C00N C00B C1 119.68(16) . . ?
N001 C00B C1 117.83(15) . . ?
C00F C00C C009 120.89(16) . . ?
C00L C00D N002 122.49(16) . . ?
C00L C00D C1 119.58(16) . . ?
N002 C00D C1 117.91(15) . . ?
C00J C00E C00M 114.23(16) . . ?
C00J C00E B2 124.11(16) . . ?
C00M C00E B2 121.61(16) . . ?
C00C C00F C008 123.30(16) . . ?
C00H C00G C00V 120.63(16) . . ?
C00H C00G C012 119.89(18) . . ?
C00V C00G C012 119.49(19) . . ?
C011 C00H N003 122.23(19) . . ?
C011 C00H C00G 119.43(18) . . ?
N003 C00H C00G 118.33(16) . . ?
N006 C00I C00R 121.75(17) . . ?
N006 C00I C00O 122.29(16) . . ?
C00R C00I C00O 115.96(17) . . ?
C00O C00J C00E 123.21(17) . . ?
C00T C00K C00A 120.18(17) . . ?
C00D C00L C00T 120.56(19) . . ?
C00R C00M C00E 123.78(17) . . ?
C00B C00N C00Z 119.93(18) . . ?
C00J C00O C00I 121.62(17) . . ?
C00Q C00P C008 123.35(16) . . ?
C00P C00Q C009 121.03(16) . . ?
C00M C00R C00I 121.19(17) . . ?
C00Z C00S C00A 120.57(17) . . ?
C00K C00T C00L 121.45(19) . . ?
C010 C00U C012 120.3(2) . . ?
C017 C00V N005 122.62(19) . . ?
C017 C00V C00G 119.44(18) . . ?
N005 C00V C00G 117.94(17) . . ?
N002 B1 N001 114.95(15) . . ?
N002 B1 C008 123.94(16) . . ?
N001 B1 C008 120.98(16) . . ?
C00S C00Z C00N 121.55(18) . . ?
C00U C010 C011 121.5(2) . . ?
C00H C011 C010 120.2(2) . . ?
C016 C012 C00U 122.8(2) . . ?
C016 C012 C00G 118.6(2) . . ?
C00U C012 C00G 118.6(2) . . ?
N003 B2 N005 114.51(16) . . ?
N003 B2 C00E 123.98(17) . . ?
N005 B2 C00E 121.45(17) . . ?
C018 C016 C012 120.9(2) . . ?
C00V C017 C018 120.7(2) . . ?
C016 C018 C017 120.8(2) . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_NBCl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2336103'
loop_
_audit_author_name
_audit_author_address
'RETWIK PARUI'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-02-28 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 B Cl N2'
_chemical_formula_weight         278.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   4.7299(7)
_cell_length_b                   10.3015(15)
_cell_length_c                   13.5889(19)
_cell_angle_alpha                90
_cell_angle_beta                 96.628(4)
_cell_angle_gamma                90
_cell_volume                     657.69(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9368
_cell_measurement_theta_min      4.23
_cell_measurement_theta_max      24.99

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.278
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12533
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.509
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2295
_reflns_number_gt                2211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.984

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.1018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2295
_refine_ls_number_parameters     187
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 1.03651(15) 0.87738(10) 0.07528(5) 0.0564(2) Uani 1 1 d . . . . .
N002 N 0.1817(5) 0.5031(2) 0.34989(16) 0.0401(5) Uani 1 1 d . . . . .
H1 H 0.252(7) 0.558(4) 0.390(2) 0.060 Uiso 1 1 d . U . . .
N003 N 0.1196(5) 0.3892(3) 0.19594(15) 0.0414(5) Uani 1 1 d . . . . .
H1A H 0.145(7) 0.377(4) 0.142(2) 0.062 Uiso 1 1 d . U . . .
C005 C 0.4630(6) 0.5879(3) 0.20810(19) 0.0370(6) Uani 1 1 d . . . . .
C006 C -0.3367(6) 0.2363(3) 0.3676(2) 0.0407(6) Uani 1 1 d . . . . .
C007 C -0.0741(5) 0.3041(2) 0.23079(19) 0.0382(6) Uani 1 1 d . . . . .
C008 C -0.2011(6) 0.2060(3) 0.1729(2) 0.0484(7) Uani 1 1 d . . . . .
H008 H -0.158757 0.195159 0.108310 0.058 Uiso 1 1 calc R U . . .
C009 C -0.0112(5) 0.4224(2) 0.39016(19) 0.0378(6) Uani 1 1 d . . . . .
B0 B 0.2537(6) 0.4917(3) 0.2522(2) 0.0369(6) Uani 1 1 d . . . . .
C00A C 0.7797(6) 0.7747(3) 0.2251(2) 0.0471(7) Uani 1 1 d . . . . .
H00A H 0.869657 0.839728 0.264534 0.056 Uiso 1 1 calc R U . . .
C00B C -0.4025(6) 0.2567(3) 0.4655(2) 0.0471(7) Uani 1 1 d . . . . .
H00B H -0.532552 0.202656 0.491654 0.057 Uiso 1 1 calc R U . . .
C00C C -0.0799(6) 0.4377(3) 0.4853(2) 0.0475(7) Uani 1 1 d . . . . .
H00C H 0.004771 0.503411 0.525345 0.057 Uiso 1 1 calc R U . . .
C00D C -0.4621(6) 0.1369(3) 0.3059(2) 0.0495(7) Uani 1 1 d . . . . .
H00D H -0.592164 0.080698 0.329772 0.059 Uiso 1 1 calc R U . . .
C00E C 0.6899(7) 0.6686(3) 0.0684(2) 0.0505(7) Uani 1 1 d . . . . .
H00E H 0.720246 0.661835 0.002177 0.061 Uiso 1 1 calc R U . . .
C00F C -0.2765(6) 0.3546(3) 0.5214(2) 0.0516(8) Uani 1 1 d . . . . .
H00F H -0.322735 0.366579 0.585426 0.062 Uiso 1 1 calc R U . . .
C00G C 0.8191(5) 0.7648(3) 0.1267(2) 0.0404(6) Uani 1 1 d . . . . .
C00H C 0.5138(7) 0.5814(3) 0.1090(2) 0.0491(7) Uani 1 1 d . . . . .
H00H H 0.426157 0.516366 0.068934 0.059 Uiso 1 1 calc R U . . .
C00I C 0.6042(6) 0.6864(3) 0.2641(2) 0.0458(7) Uani 1 1 d . . . . .
H00I H 0.579074 0.692884 0.330822 0.055 Uiso 1 1 calc R U . . .
C00J C -0.3948(7) 0.1224(3) 0.2116(2) 0.0521(7) Uani 1 1 d . . . . .
H00J H -0.478706 0.055802 0.172224 0.063 Uiso 1 1 calc R U . . .
C4 C -0.1388(5) 0.3213(2) 0.32947(18) 0.0364(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00G 1.748(3) . ?
N002 C009 1.392(3) . ?
N002 B0 1.413(4) . ?
N003 C007 1.390(4) . ?
N003 B0 1.411(4) . ?
C005 C00I 1.392(4) . ?
C005 C00H 1.397(4) . ?
C005 B0 1.567(4) . ?
C006 C00D 1.410(4) . ?
C006 C00B 1.417(4) . ?
C006 C4 1.422(4) . ?
C007 C008 1.375(4) . ?
C007 C4 1.420(4) . ?
C008 C00J 1.403(4) . ?
C009 C00C 1.377(4) . ?
C009 C4 1.420(4) . ?
C00A C00G 1.375(4) . ?
C00A C00I 1.378(4) . ?
C00B C00F 1.358(4) . ?
C00C C00F 1.394(4) . ?
C00D C00J 1.364(4) . ?
C00E C00G 1.368(4) . ?
C00E C00H 1.382(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 N002 B0 124.0(2) . . ?
C007 N003 B0 124.1(2) . . ?
C00I C005 C00H 115.9(2) . . ?
C00I C005 B0 122.4(2) . . ?
C00H C005 B0 121.7(2) . . ?
C00D C006 C00B 122.9(3) . . ?
C00D C006 C4 118.7(2) . . ?
C00B C006 C4 118.4(3) . . ?
C008 C007 N003 122.0(2) . . ?
C008 C007 C4 120.2(2) . . ?
N003 C007 C4 117.7(2) . . ?
C007 C008 C00J 119.9(3) . . ?
C00C C009 N002 122.5(2) . . ?
C00C C009 C4 119.9(2) . . ?
N002 C009 C4 117.6(2) . . ?
N003 B0 N002 115.4(2) . . ?
N003 B0 C005 122.0(2) . . ?
N002 B0 C005 122.5(2) . . ?
C00G C00A C00I 118.8(3) . . ?
C00F C00B C006 120.3(3) . . ?
C009 C00C C00F 119.9(3) . . ?
C00J C00D C006 120.7(3) . . ?
C00G C00E C00H 119.3(3) . . ?
C00B C00F C00C 121.8(2) . . ?
C00E C00G C00A 121.0(3) . . ?
C00E C00G Cl01 119.6(2) . . ?
C00A C00G Cl01 119.5(2) . . ?
C00E C00H C005 122.2(3) . . ?
C00A C00I C005 122.9(3) . . ?
C00D C00J C008 121.2(3) . . ?
C009 C4 C007 121.1(2) . . ?
C009 C4 C006 119.6(2) . . ?
C007 C4 C006 119.3(2) . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_test1_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2336105'
loop_
_audit_author_name
_audit_author_address
'RETWIK PARUI'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-02-28 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 B F N2'
_chemical_formula_weight         262.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -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.
;

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

_cell_length_a                   22.7941(12)
_cell_length_b                   22.7941(12)
_cell_length_c                   5.0803(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2639.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43785
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.263
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2326
_reflns_number_gt                1600
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+1.5157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 566 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2326
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.11169(17) 0.58476(15) -0.2445(9) 0.1024(13) Uani 1 1 d . . . . .
N002 N 0.30724(18) 0.46322(18) 0.5252(9) 0.0627(12) Uani 1 1 d . . . . .
H002 H 0.323786 0.487176 0.417577 0.075 Uiso 1 1 calc R U . . .
N003 N 0.21988(19) 0.41797(18) 0.6992(9) 0.0650(12) Uani 1 1 d . . . . .
H003 H 0.182333 0.414228 0.700363 0.078 Uiso 1 1 calc R U . . .
C1 C 0.2072(2) 0.4950(2) 0.3229(10) 0.0548(12) Uani 1 1 d . . . . .
C005 C 0.3428(2) 0.4310(2) 0.6982(12) 0.0658(15) Uani 1 1 d . . . . .
C006 C 0.3147(3) 0.3918(2) 0.8745(11) 0.0638(15) Uani 1 1 d . . . . .
C007 C 0.2529(3) 0.3838(2) 0.8762(11) 0.0654(14) Uani 1 1 d . . . . .
C008 C 0.1428(3) 0.5555(3) -0.0513(12) 0.0702(15) Uani 1 1 d . . . . .
C009 C 0.1509(2) 0.4772(2) 0.2464(11) 0.0669(14) Uani 1 1 d . . . . .
H009 H 0.134802 0.443844 0.323242 0.080 Uiso 1 1 calc R U . . .
C00A C 0.1180(3) 0.5076(3) 0.0597(13) 0.0758(16) Uani 1 1 d . . . . .
H00A H 0.080488 0.495420 0.013218 0.091 Uiso 1 1 calc R U . . .
C00B C 0.2285(2) 0.5458(2) 0.2045(13) 0.0725(15) Uani 1 1 d . . . . .
H00B H 0.265361 0.559752 0.252245 0.087 Uiso 1 1 calc R U . . .
C00C C 0.4115(3) 0.3682(3) 1.0552(15) 0.097(2) Uani 1 1 d . . . . .
H00C H 0.434921 0.348420 1.175809 0.117 Uiso 1 1 calc R U . . .
C00D C 0.4031(2) 0.4371(3) 0.7013(13) 0.0794(17) Uani 1 1 d . . . . .
H00D H 0.421331 0.462417 0.583408 0.095 Uiso 1 1 calc R U . . .
C00E C 0.3502(3) 0.3588(3) 1.0585(13) 0.0798(19) Uani 1 1 d . . . . .
C00F C 0.1960(3) 0.5767(3) 0.0153(14) 0.0802(18) Uani 1 1 d . . . . .
H00F H 0.210630 0.610661 -0.061689 0.096 Uiso 1 1 calc R U . . .
C00G C 0.2621(4) 0.3130(3) 1.2252(14) 0.094(2) Uani 1 1 d . . . . .
H00G H 0.244424 0.286615 1.340276 0.113 Uiso 1 1 calc R U . . .
C00H C 0.4368(3) 0.4052(3) 0.8810(16) 0.095(2) Uani 1 1 d . . . . .
H00H H 0.477382 0.409447 0.880824 0.114 Uiso 1 1 calc R U . . .
C00I C 0.2264(3) 0.3452(3) 1.0474(12) 0.0802(17) Uani 1 1 d . . . . .
H00I H 0.185892 0.340224 1.046503 0.096 Uiso 1 1 calc R U . . .
C00J C 0.3213(4) 0.3197(3) 1.2319(15) 0.099(2) Uani 1 1 d . . . . .
H00J H 0.343286 0.298259 1.352445 0.119 Uiso 1 1 calc R U . . .
B1 B 0.2450(3) 0.4580(2) 0.5199(13) 0.0583(15) 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
F001 C008 1.382(7) . ?
N002 C005 1.403(7) . ?
N002 B1 1.423(7) . ?
N003 C007 1.408(7) . ?
N003 B1 1.412(7) . ?
C1 C00B 1.394(7) . ?
C1 C009 1.402(7) . ?
C1 B1 1.566(8) . ?
C005 C00D 1.382(7) . ?
C005 C006 1.417(8) . ?
C006 C007 1.422(8) . ?
C006 C00E 1.447(8) . ?
C007 C00I 1.378(8) . ?
C008 C00F 1.348(8) . ?
C008 C00A 1.353(8) . ?
C009 C00A 1.393(8) . ?
C00B C00F 1.403(8) . ?
C00C C00H 1.352(10) . ?
C00C C00E 1.412(9) . ?
C00D C00H 1.397(9) . ?
C00E C00J 1.416(10) . ?
C00G C00J 1.361(10) . ?
C00G C00I 1.419(9) . ?

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
C005 N002 B1 123.0(5) . . ?
C007 N003 B1 123.6(5) . . ?
C00B C1 C009 116.1(5) . . ?
C00B C1 B1 122.1(5) . . ?
C009 C1 B1 121.8(5) . . ?
C00D C005 N002 122.0(6) . . ?
C00D C005 C006 120.3(5) . . ?
N002 C005 C006 117.7(5) . . ?
C007 C006 C005 122.2(5) . . ?
C007 C006 C00E 118.9(6) . . ?
C005 C006 C00E 118.9(5) . . ?
C00I C007 N003 121.5(5) . . ?
C00I C007 C006 121.4(5) . . ?
N003 C007 C006 117.1(5) . . ?
C00F C008 C00A 124.0(5) . . ?
C00F C008 F001 117.9(6) . . ?
C00A C008 F001 118.1(5) . . ?
C00A C009 C1 122.5(5) . . ?
C008 C00A C009 117.5(5) . . ?
C1 C00B C00F 121.9(5) . . ?
C00H C00C C00E 121.6(7) . . ?
C005 C00D C00H 120.2(7) . . ?
C00J C00E C00C 124.2(7) . . ?
C00J C00E C006 118.0(7) . . ?
C00C C00E C006 117.8(7) . . ?
C008 C00F C00B 117.9(5) . . ?
C00J C00G C00I 121.8(7) . . ?
C00C C00H C00D 121.1(7) . . ?
C007 C00I C00G 118.8(7) . . ?
C00G C00J C00E 121.2(6) . . ?
N003 B1 N002 116.5(5) . . ?
N003 B1 C1 122.4(5) . . ?
N002 B1 C1 121.1(5) . . ?

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_TEST_0m_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2336092'
loop_
_audit_author_name
_audit_author_address
'RETWIK PARUI'
;INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI
India
;
_audit_update_record             
;
2024-02-28 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 B Br N2'
_chemical_formula_weight         323.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.963(9)
_cell_length_b                   6.412(4)
_cell_length_c                   16.767(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.356(19)
_cell_angle_gamma                90
_cell_volume                     1392.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9322
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.941
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34504
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.947
_diffrn_reflns_theta_max         26.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2791
_reflns_number_gt                2359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2791
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.17457(3) 1.06950(5) 0.56223(2) 0.06296(19) Uani 1 1 d . . . . .
N002 N 0.51853(17) 0.2033(3) 0.62873(13) 0.0427(5) Uani 1 1 d . . . . .
H002 H 0.518642 0.232605 0.578678 0.051 Uiso 1 1 calc R U . . .
N003 N 0.46692(18) 0.2826(3) 0.76110(13) 0.0445(5) Uani 1 1 d . . . . .
H003 H 0.436059 0.362579 0.793692 0.053 Uiso 1 1 calc R U . . .
C004 C 0.56907(19) -0.0249(4) 0.73805(16) 0.0381(5) Uani 1 1 d . . . . .
C005 C 0.3985(2) 0.5298(4) 0.64812(16) 0.0386(6) Uani 1 1 d . . . . .
C006 C 0.36760(19) 0.6871(4) 0.70029(15) 0.0399(6) Uani 1 1 d . . . . .
H006 H 0.390906 0.682182 0.753462 0.048 Uiso 1 1 calc R U . . .
C007 C 0.5716(2) 0.0259(4) 0.65546(16) 0.0385(5) Uani 1 1 d . . . . .
C008 C 0.5167(2) 0.1051(4) 0.79210(16) 0.0417(6) Uani 1 1 d . . . . .
C009 C 0.3034(2) 0.8500(4) 0.67521(16) 0.0430(6) Uani 1 1 d . . . . .
H009 H 0.284357 0.953152 0.710719 0.052 Uiso 1 1 calc R U . . .
C00A C 0.6248(2) -0.1015(4) 0.60489(19) 0.0500(7) Uani 1 1 d . . . . .
H00A H 0.626739 -0.068981 0.550914 0.060 Uiso 1 1 calc R U . . .
C00B C 0.2684(2) 0.8549(4) 0.59628(17) 0.0435(6) Uani 1 1 d . . . . .
C00C C 0.61934(19) -0.2094(4) 0.76725(17) 0.0431(6) Uani 1 1 d . . . . .
C00D C 0.2984(2) 0.7056(5) 0.54197(17) 0.0505(7) Uani 1 1 d . . . . .
H00D H 0.275304 0.712099 0.488780 0.061 Uiso 1 1 calc R U . . .
C00E C 0.3632(3) 0.5470(4) 0.56856(18) 0.0493(7) Uani 1 1 d . . . . .
H00E H 0.384123 0.447938 0.532096 0.059 Uiso 1 1 calc R U . . .
C00F C 0.6724(2) -0.3359(5) 0.7133(2) 0.0526(7) Uani 1 1 d . . . . .
H00F H 0.704915 -0.457318 0.731356 0.063 Uiso 1 1 calc R U . . .
C00G C 0.5132(3) 0.0503(5) 0.8712(2) 0.0612(9) Uani 1 1 d . . . . .
H00G H 0.478407 0.134736 0.906324 0.073 Uiso 1 1 calc R U . . .
C00H C 0.6759(2) -0.2802(5) 0.6349(2) 0.0563(8) Uani 1 1 d . . . . .
H00H H 0.713078 -0.362375 0.600479 0.068 Uiso 1 1 calc R U . . .
C00I C 0.6135(2) -0.2603(5) 0.84897(19) 0.0568(8) Uani 1 1 d . . . . .
H00I H 0.644975 -0.381180 0.868681 0.068 Uiso 1 1 calc R U . . .
B1 B 0.4641(2) 0.3388(5) 0.67954(18) 0.0396(6) Uani 1 1 d . . . . .
C00K C 0.5620(3) -0.1333(6) 0.8992(2) 0.0666(9) Uani 1 1 d . . . . .
H00K H 0.559077 -0.168662 0.952803 0.080 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
Br01 C00B 1.908(3) . ?
N002 C007 1.394(3) . ?
N002 B1 1.424(4) . ?
N003 C008 1.398(3) . ?
N003 B1 1.413(4) . ?
C004 C008 1.424(4) . ?
C004 C007 1.424(4) . ?
C004 C00C 1.428(4) . ?
C005 C00E 1.397(4) . ?
C005 C006 1.405(4) . ?
C005 B1 1.569(4) . ?
C006 C009 1.390(4) . ?
C007 C00A 1.382(4) . ?
C008 C00G 1.375(4) . ?
C009 C00B 1.381(4) . ?
C00A C00H 1.407(4) . ?
C00B C00D 1.388(4) . ?
C00C C00F 1.414(4) . ?
C00C C00I 1.414(4) . ?
C00D C00E 1.381(4) . ?
C00F C00H 1.366(5) . ?
C00G C00K 1.408(5) . ?
C00I C00K 1.365(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 N002 B1 123.8(2) . . ?
C008 N003 B1 124.1(2) . . ?
C008 C004 C007 121.1(2) . . ?
C008 C004 C00C 119.3(2) . . ?
C007 C004 C00C 119.6(2) . . ?
C00E C005 C006 116.6(2) . . ?
C00E C005 B1 122.3(2) . . ?
C006 C005 B1 121.1(2) . . ?
C009 C006 C005 122.3(2) . . ?
C00A C007 N002 122.5(3) . . ?
C00A C007 C004 119.6(3) . . ?
N002 C007 C004 117.9(2) . . ?
C00G C008 N003 122.2(3) . . ?
C00G C008 C004 120.0(3) . . ?
N003 C008 C004 117.7(2) . . ?
C00B C009 C006 118.4(2) . . ?
C007 C00A C00H 120.1(3) . . ?
C009 C00B C00D 121.5(3) . . ?
C009 C00B Br01 118.9(2) . . ?
C00D C00B Br01 119.6(2) . . ?
C00F C00C C00I 122.3(3) . . ?
C00F C00C C004 118.9(3) . . ?
C00I C00C C004 118.8(2) . . ?
C00E C00D C00B 118.6(3) . . ?
C00D C00E C005 122.5(3) . . ?
C00H C00F C00C 120.2(3) . . ?
C008 C00G C00K 120.2(3) . . ?
C00F C00H C00A 121.5(3) . . ?
C00K C00I C00C 120.4(3) . . ?
N003 B1 N002 115.4(2) . . ?
N003 B1 C005 121.1(2) . . ?
N002 B1 C005 123.4(2) . . ?
C00I C00K C00G 121.2(3) . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.130

####################################################################### 
# 
# 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_nbcn_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2336104'
loop_
_audit_author_name
_audit_author_address
'RETWIK PARUI'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-02-28 deposited with the CCDC.	2025-02-28 downloaded from the CCDC.
;
_audit_creation_date             2023-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 B N3'
_chemical_formula_sum            'C17 H12 B N3'
_chemical_formula_weight         269.11
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.2259(7)
_cell_length_b                   26.151(2)
_cell_length_c                   19.2586(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.282(2)
_cell_angle_gamma                90
_cell_volume                     4125.2(6)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6222
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1555 before and 0.0747 after correction.
The Ratio of minimum to maximum transmission is 0.8349.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            82066
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.317
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                5064
_reflns_number_total             7172
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     587
_refine_ls_number_reflns         7172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0849
_refine_ls_restrained_S_all      1.154
_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)+(0.0327P)²+5.2457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00J(H00J), C00L(H00L), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00S(H00S), C00U(H00U), C00Y(H00Y), C00Z(H00Z), C010(H010), C015(H015),
 C016(H016), C018(H018), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C),
 C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I),
 C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N), C01P(H01P)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
N001 N 0.6248(4) 0.61531(11) 0.01684(14) 0.0502(7) Uani 1 1 d . . . . .
H001 H 0.716(5) 0.6037(15) 0.007(2) 0.075 Uiso 1 1 d . U . . .
N002 N 0.3355(4) 0.62555(11) -0.00580(14) 0.0482(7) Uani 1 1 d . . . . .
H002 H 0.240(5) 0.6218(15) -0.0297(19) 0.072 Uiso 1 1 d . U . . .
N003 N 0.7760(4) 0.36624(11) 0.67218(14) 0.0522(7) Uani 1 1 d . . . . .
H003 H 0.684(5) 0.3699(15) 0.693(2) 0.078 Uiso 1 1 d . U . . .
N004 N 1.0512(4) 0.38834(12) 0.65369(15) 0.0569(8) Uani 1 1 d . . . . .
H004 H 1.145(5) 0.4012(16) 0.666(2) 0.085 Uiso 1 1 d . U . . .
N005 N 0.5978(4) 0.36690(11) 0.33879(14) 0.0540(8) Uani 1 1 d . . . . .
H005 H 0.504(5) 0.3703(15) 0.357(2) 0.081 Uiso 1 1 d . U . . .
N006 N 0.8745(4) 0.38913(12) 0.32433(15) 0.0574(8) Uani 1 1 d . . . . .
H006 H 0.970(5) 0.4012(16) 0.339(2) 0.086 Uiso 1 1 d . U . . .
C007 C 0.4770(4) 0.66544(11) 0.09501(15) 0.0410(7) Uani 1 1 d . . . . .
C008 C 0.3301(4) 0.65807(11) 0.05156(16) 0.0427(8) Uani 1 1 d . . . . .
C009 C 0.6270(4) 0.64411(12) 0.07797(16) 0.0443(8) Uani 1 1 d . . . . .
C00A C 0.7276(4) 0.33339(11) 0.24122(16) 0.0439(8) Uani 1 1 d . . . . .
C00B C 0.5876(4) 0.33620(12) 0.27903(16) 0.0478(8) Uani 1 1 d . . . . .
C00C C 0.8985(4) 0.33247(12) 0.57256(16) 0.0465(8) Uani 1 1 d . . . . .
C00D C 0.7617(4) 0.33543(12) 0.61253(17) 0.0490(8) Uani 1 1 d . . . . .
C00E C 0.4780(4) 0.56599(12) -0.08897(16) 0.0462(8) Uani 1 1 d . . . . .
C00F C 0.5498(4) 0.57694(13) -0.14959(17) 0.0555(9) Uani 1 1 d . . . . .
H00F H 0.604814 0.607798 -0.152837 0.067 Uiso 1 1 calc R U . . .
C00G C 0.4748(4) 0.69515(12) 0.15659(16) 0.0479(8) Uani 1 1 d . . . . .
C00H C 1.0459(4) 0.35803(12) 0.59379(17) 0.0497(8) Uani 1 1 d . . . . .
C00I C 0.9340(4) 0.50110(13) 0.86776(16) 0.0493(8) Uani 1 1 d . . . . .
C00J C 0.8409(4) 0.42281(13) 0.81532(16) 0.0528(9) Uani 1 1 d . . . . .
H00J H 0.779810 0.392996 0.817236 0.063 Uiso 1 1 calc R U . . .
C00K C 0.8741(4) 0.35910(13) 0.26422(17) 0.0495(8) Uani 1 1 d . . . . .
C00L C 0.5424(4) 0.54365(14) -0.20515(17) 0.0575(10) Uani 1 1 d . . . . .
H00L H 0.590037 0.552364 -0.245499 0.069 Uiso 1 1 calc R U . . .
N00M N 0.7377(4) 0.56743(15) 0.63612(18) 0.0810(11) Uani 1 1 d . . . . .
C00N C 0.7198(5) 0.30413(12) 0.17872(17) 0.0507(9) Uani 1 1 d . . . . .
C00O C 0.3256(5) 0.71782(13) 0.17102(19) 0.0590(10) Uani 1 1 d . . . . .
H00O H 0.321665 0.737520 0.211025 0.071 Uiso 1 1 calc R U . . .
C00P C 0.6526(4) 0.42160(14) 0.48387(17) 0.0552(9) Uani 1 1 d . . . . .
H00P H 0.596250 0.390861 0.485628 0.066 Uiso 1 1 calc R U . . .
C00Q C 0.7668(4) 0.65105(14) 0.12145(19) 0.0575(9) Uani 1 1 d . . . . .
H00Q H 0.864412 0.636507 0.110526 0.069 Uiso 1 1 calc R U . . .
N00R N 0.4388(4) 0.43342(15) -0.30323(18) 0.0819(11) Uani 1 1 d . . . . .
C00S C 0.6507(4) 0.45543(14) 0.53876(17) 0.0558(9) Uani 1 1 d . . . . .
H00S H 0.595781 0.447118 0.577328 0.067 Uiso 1 1 calc R U . . .
N00T N 0.9474(4) 0.56674(14) 0.96850(18) 0.0782(10) Uani 1 1 d . . . . .
C00U C 0.1887(4) 0.68114(13) 0.06740(18) 0.0540(9) Uani 1 1 d . . . . .
H00U H 0.093113 0.676769 0.038275 0.065 Uiso 1 1 calc R U . . .
C00V C 0.4644(4) 0.49748(13) -0.20070(16) 0.0508(9) Uani 1 1 d . . . . .
C00W C 0.9232(4) 0.43185(13) 0.75711(16) 0.0501(8) Uani 1 1 d . . . . .
C00X C 0.7309(4) 0.50174(14) 0.53615(17) 0.0528(9) Uani 1 1 d . . . . .
C00Y C 0.1880(5) 0.71125(14) 0.1273(2) 0.0616(10) Uani 1 1 d . . . . .
H00Y H 0.091695 0.727049 0.137480 0.074 Uiso 1 1 calc R U . . .
C00Z C 0.8460(4) 0.45631(14) 0.87047(17) 0.0561(9) Uani 1 1 d . . . . .
H00Z H 0.790699 0.448883 0.909239 0.067 Uiso 1 1 calc R U . . .
C010 C 0.8598(5) 0.30172(14) 0.14178(19) 0.0629(10) Uani 1 1 d . . . . .
H010 H 0.856578 0.283112 0.100528 0.076 Uiso 1 1 calc R U . . .
C011 C 0.7362(4) 0.43212(13) 0.42607(16) 0.0525(9) Uani 1 1 d . . . . .
C012 C 0.8867(5) 0.30305(13) 0.51066(18) 0.0581(10) Uani 1 1 d . . . . .
C013 C 0.9403(4) 0.53741(15) 0.92445(19) 0.0581(9) Uani 1 1 d . . . . .
C014 C 0.7325(4) 0.53781(16) 0.59245(19) 0.0610(10) Uani 1 1 d . . . . .
C015 C 0.7624(5) 0.68011(15) 0.1824(2) 0.0650(10) Uani 1 1 d . . . . .
H015 H 0.857724 0.684670 0.211619 0.078 Uiso 1 1 calc R U . . .
C016 C 0.4010(5) 0.51903(14) -0.08608(17) 0.0616(10) Uani 1 1 d . . . . .
H016 H 0.351997 0.510424 -0.046050 0.074 Uiso 1 1 calc R U . . .
C017 C 0.4531(5) 0.46207(16) -0.25834(19) 0.0620(10) Uani 1 1 d . . . . .
C018 C 1.0164(5) 0.51195(14) 0.81015(19) 0.0652(11) Uani 1 1 d . . . . .
H018 H 1.074218 0.542358 0.807782 0.078 Uiso 1 1 calc R U . . .
C019 C 0.4482(5) 0.31044(13) 0.2559(2) 0.0622(10) Uani 1 1 d . . . . .
H019 H 0.357068 0.312075 0.281026 0.075 Uiso 1 1 calc R U . . .
B1 B 0.7372(5) 0.39445(15) 0.3628(2) 0.0516(10) Uani 1 1 d . . . . .
B2 B 0.9170(5) 0.39434(15) 0.69355(19) 0.0495(10) Uani 1 1 d . . . . .
B3 B 0.4811(5) 0.60365(14) -0.02541(19) 0.0452(9) Uani 1 1 d . . . . .
C01A C 1.0117(5) 0.47727(14) 0.75638(18) 0.0642(10) Uani 1 1 d . . . . .
H01A H 1.069612 0.484337 0.718237 0.077 Uiso 1 1 calc R U . . .
C01B C 0.6207(5) 0.30960(14) 0.5918(2) 0.0636(10) Uani 1 1 d . . . . .
H01B H 0.531828 0.311186 0.618246 0.076 Uiso 1 1 calc R U . . .
C01C C 0.6214(5) 0.70173(14) 0.19958(19) 0.0622(10) Uani 1 1 d . . . . .
H01C H 0.621628 0.721069 0.240118 0.075 Uiso 1 1 calc R U . . .
C01D C 0.9990(5) 0.32619(15) 0.1657(2) 0.0701(11) Uani 1 1 d . . . . .
H01D H 1.090365 0.323776 0.140767 0.084 Uiso 1 1 calc R U . . .
C01E C 1.0078(5) 0.35501(15) 0.2270(2) 0.0654(10) Uani 1 1 d . . . . .
H01E H 1.104562 0.371443 0.242656 0.078 Uiso 1 1 calc R U . . .
C01F C 1.0246(6) 0.30007(15) 0.4719(2) 0.0736(12) Uani 1 1 d . . . . .
H01F H 1.018424 0.281342 0.430656 0.088 Uiso 1 1 calc R U . . .
C01G C 1.1779(5) 0.35305(15) 0.5553(2) 0.0673(11) Uani 1 1 d . . . . .
H01G H 1.276036 0.368992 0.570102 0.081 Uiso 1 1 calc R U . . .
C01H C 0.3946(5) 0.48464(14) -0.14045(18) 0.0640(10) Uani 1 1 d . . . . .
H01H H 0.343752 0.453127 -0.136669 0.077 Uiso 1 1 calc R U . . .
C01I C 0.5736(5) 0.27882(14) 0.1567(2) 0.0665(11) Uani 1 1 d . . . . .
H01I H 0.566149 0.259854 0.115659 0.080 Uiso 1 1 calc R U . . .
C01J C 0.4427(5) 0.28179(15) 0.1948(2) 0.0712(11) Uani 1 1 d . . . . .
H01J H 0.347447 0.264312 0.179719 0.085 Uiso 1 1 calc R U . . .
C01K C 0.6117(6) 0.28068(15) 0.5301(2) 0.0757(12) Uani 1 1 d . . . . .
H01K H 0.515842 0.263138 0.516137 0.091 Uiso 1 1 calc R U . . .
C01L C 0.7384(6) 0.27768(14) 0.4904(2) 0.0737(12) Uani 1 1 d . . . . .
H01L H 0.727880 0.258725 0.449399 0.088 Uiso 1 1 calc R U . . .
C01M C 0.8150(5) 0.47911(15) 0.42544(19) 0.0698(11) Uani 1 1 d . . . . .
H01M H 0.871476 0.487436 0.387309 0.084 Uiso 1 1 calc R U . . .
C01N C 0.8127(5) 0.51361(15) 0.47886(19) 0.0710(11) Uani 1 1 d . . . . .
H01N H 0.866018 0.544839 0.476536 0.085 Uiso 1 1 calc R U . . .
C01P C 1.1648(6) 0.32415(16) 0.4942(2) 0.0783(13) Uani 1 1 d . . . . .
H01P H 1.254441 0.321423 0.468343 0.094 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
N001 H001 0.85(4) . ?
N001 C009 1.396(4) . ?
N001 B3 1.405(5) . ?
N002 H002 0.88(4) . ?
N002 C008 1.398(4) . ?
N002 B3 1.410(5) . ?
N003 H003 0.89(4) . ?
N003 C00D 1.399(4) . ?
N003 B2 1.403(5) . ?
N004 H004 0.86(4) . ?
N004 C00H 1.397(4) . ?
N004 B2 1.410(5) . ?
N005 H005 0.89(4) . ?
N005 C00B 1.399(4) . ?
N005 B1 1.396(5) . ?
N006 H006 0.87(4) . ?
N006 C00K 1.399(4) . ?
N006 B1 1.413(5) . ?
C007 C008 1.418(4) . ?
C007 C009 1.420(4) . ?
C007 C00G 1.419(4) . ?
C008 C00U 1.370(4) . ?
C009 C00Q 1.371(5) . ?
C00A C00B 1.419(5) . ?
C00A C00K 1.416(5) . ?
C00A C00N 1.423(4) . ?
C00B C019 1.369(5) . ?
C00C C00D 1.423(5) . ?
C00C C00H 1.412(5) . ?
C00C C012 1.415(5) . ?
C00D C01B 1.370(5) . ?
C00E C00F 1.386(4) . ?
C00E C016 1.385(5) . ?
C00E B3 1.570(5) . ?
C00F H00F 0.9300 . ?
C00F C00L 1.376(5) . ?
C00G C00O 1.413(5) . ?
C00G C01C 1.409(5) . ?
C00H C01G 1.376(5) . ?
C00I C00Z 1.380(5) . ?
C00I C013 1.444(5) . ?
C00I C018 1.381(5) . ?
C00J H00J 0.9300 . ?
C00J C00W 1.382(4) . ?
C00J C00Z 1.374(5) . ?
C00K C01E 1.370(5) . ?
C00L H00L 0.9300 . ?
C00L C00V 1.374(5) . ?
N00M C014 1.141(4) . ?
C00N C010 1.410(5) . ?
C00N C01I 1.404(5) . ?
C00O H00O 0.9300 . ?
C00O C00Y 1.357(5) . ?
C00P H00P 0.9300 . ?
C00P C00S 1.380(5) . ?
C00P C011 1.389(5) . ?
C00Q H00Q 0.9300 . ?
C00Q C015 1.402(5) . ?
N00R C017 1.142(4) . ?
C00S H00S 0.9300 . ?
C00S C00X 1.382(5) . ?
N00T C013 1.141(4) . ?
C00U H00U 0.9300 . ?
C00U C00Y 1.398(5) . ?
C00V C017 1.442(5) . ?
C00V C01H 1.383(5) . ?
C00W B2 1.566(5) . ?
C00W C01A 1.394(5) . ?
C00X C014 1.436(5) . ?
C00X C01N 1.380(5) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C010 C01D 1.354(5) . ?
C011 B1 1.568(5) . ?
C011 C01M 1.390(5) . ?
C012 C01F 1.417(6) . ?
C012 C01L 1.412(6) . ?
C015 H015 0.9300 . ?
C015 C01C 1.358(5) . ?
C016 H016 0.9300 . ?
C016 C01H 1.378(5) . ?
C018 H018 0.9300 . ?
C018 C01A 1.374(5) . ?
C019 H019 0.9300 . ?
C019 C01J 1.392(5) . ?
C01A H01A 0.9300 . ?
C01B H01B 0.9300 . ?
C01B C01K 1.405(5) . ?
C01C H01C 0.9300 . ?
C01D H01D 0.9300 . ?
C01D C01E 1.398(5) . ?
C01E H01E 0.9300 . ?
C01F H01F 0.9300 . ?
C01F C01P 1.349(6) . ?
C01G H01G 0.9300 . ?
C01G C01P 1.394(5) . ?
C01H H01H 0.9300 . ?
C01I H01I 0.9300 . ?
C01I C01J 1.360(5) . ?
C01J H01J 0.9300 . ?
C01K H01K 0.9300 . ?
C01K C01L 1.349(6) . ?
C01L H01L 0.9300 . ?
C01M H01M 0.9300 . ?
C01M C01N 1.370(5) . ?
C01N H01N 0.9300 . ?
C01P H01P 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 N001 H001 116(3) . . ?
C009 N001 B3 123.4(3) . . ?
B3 N001 H001 120(3) . . ?
C008 N002 H002 113(2) . . ?
C008 N002 B3 123.2(3) . . ?
B3 N002 H002 124(2) . . ?
C00D N003 H003 115(3) . . ?
C00D N003 B2 123.2(3) . . ?
B2 N003 H003 121(3) . . ?
C00H N004 H004 114(3) . . ?
C00H N004 B2 123.1(3) . . ?
B2 N004 H004 123(3) . . ?
C00B N005 H005 114(3) . . ?
B1 N005 H005 122(3) . . ?
B1 N005 C00B 123.6(3) . . ?
C00K N006 H006 114(3) . . ?
C00K N006 B1 123.2(3) . . ?
B1 N006 H006 123(3) . . ?
C008 C007 C009 121.4(3) . . ?
C008 C007 C00G 119.5(3) . . ?
C009 C007 C00G 119.1(3) . . ?
N002 C008 C007 117.5(3) . . ?
C00U C008 N002 122.2(3) . . ?
C00U C008 C007 120.2(3) . . ?
N001 C009 C007 117.6(3) . . ?
C00Q C009 N001 122.1(3) . . ?
C00Q C009 C007 120.3(3) . . ?
C00B C00A C00N 119.1(3) . . ?
C00K C00A C00B 121.5(3) . . ?
C00K C00A C00N 119.4(3) . . ?
N005 C00B C00A 117.5(3) . . ?
C019 C00B N005 122.3(3) . . ?
C019 C00B C00A 120.2(3) . . ?
C00H C00C C00D 121.2(3) . . ?
C00H C00C C012 119.5(3) . . ?
C012 C00C C00D 119.3(3) . . ?
N003 C00D C00C 117.7(3) . . ?
C01B C00D N003 121.9(3) . . ?
C01B C00D C00C 120.4(3) . . ?
C00F C00E B3 123.3(3) . . ?
C016 C00E C00F 116.7(3) . . ?
C016 C00E B3 120.0(3) . . ?
C00E C00F H00F 118.9 . . ?
C00L C00F C00E 122.2(3) . . ?
C00L C00F H00F 118.9 . . ?
C00O C00G C007 118.1(3) . . ?
C01C C00G C007 118.8(3) . . ?
C01C C00G C00O 123.0(3) . . ?
N004 C00H C00C 117.9(3) . . ?
C01G C00H N004 122.2(3) . . ?
C01G C00H C00C 119.9(3) . . ?
C00Z C00I C013 120.8(3) . . ?
C018 C00I C00Z 120.1(3) . . ?
C018 C00I C013 119.1(3) . . ?
C00W C00J H00J 118.8 . . ?
C00Z C00J H00J 118.8 . . ?
C00Z C00J C00W 122.4(3) . . ?
N006 C00K C00A 117.6(3) . . ?
C01E C00K N006 122.4(3) . . ?
C01E C00K C00A 120.0(3) . . ?
C00F C00L H00L 120.2 . . ?
C00V C00L C00F 119.7(3) . . ?
C00V C00L H00L 120.2 . . ?
C010 C00N C00A 118.4(3) . . ?
C01I C00N C00A 118.7(3) . . ?
C01I C00N C010 122.9(3) . . ?
C00G C00O H00O 119.5 . . ?
C00Y C00O C00G 121.0(3) . . ?
C00Y C00O H00O 119.5 . . ?
C00S C00P H00P 119.1 . . ?
C00S C00P C011 121.9(3) . . ?
C011 C00P H00P 119.1 . . ?
C009 C00Q H00Q 120.0 . . ?
C009 C00Q C015 119.9(4) . . ?
C015 C00Q H00Q 120.0 . . ?
C00P C00S H00S 120.2 . . ?
C00P C00S C00X 119.7(3) . . ?
C00X C00S H00S 120.2 . . ?
C008 C00U H00U 120.0 . . ?
C008 C00U C00Y 120.0(3) . . ?
C00Y C00U H00U 120.0 . . ?
C00L C00V C017 120.9(3) . . ?
C00L C00V C01H 119.9(3) . . ?
C01H C00V C017 119.2(3) . . ?
C00J C00W B2 123.0(3) . . ?
C00J C00W C01A 116.7(3) . . ?
C01A C00W B2 120.3(3) . . ?
C00S C00X C014 121.3(3) . . ?
C01N C00X C00S 119.7(3) . . ?
C01N C00X C014 119.0(4) . . ?
C00O C00Y C00U 121.1(3) . . ?
C00O C00Y H00Y 119.5 . . ?
C00U C00Y H00Y 119.5 . . ?
C00I C00Z H00Z 120.3 . . ?
C00J C00Z C00I 119.4(3) . . ?
C00J C00Z H00Z 120.3 . . ?
C00N C010 H010 119.6 . . ?
C01D C010 C00N 120.8(3) . . ?
C01D C010 H010 119.6 . . ?
C00P C011 B1 122.5(3) . . ?
C00P C011 C01M 116.6(3) . . ?
C01M C011 B1 120.8(3) . . ?
C00C C012 C01F 118.6(4) . . ?
C01L C012 C00C 118.6(4) . . ?
C01L C012 C01F 122.8(4) . . ?
N00T C013 C00I 178.6(5) . . ?
N00M C014 C00X 177.6(4) . . ?
C00Q C015 H015 119.4 . . ?
C01C C015 C00Q 121.2(4) . . ?
C01C C015 H015 119.4 . . ?
C00E C016 H016 118.9 . . ?
C01H C016 C00E 122.3(3) . . ?
C01H C016 H016 118.9 . . ?
N00R C017 C00V 177.5(4) . . ?
C00I C018 H018 120.4 . . ?
C01A C018 C00I 119.2(3) . . ?
C01A C018 H018 120.4 . . ?
C00B C019 H019 120.0 . . ?
C00B C019 C01J 120.1(4) . . ?
C01J C019 H019 120.0 . . ?
N005 B1 N006 116.6(3) . . ?
N005 B1 C011 121.2(3) . . ?
N006 B1 C011 122.1(3) . . ?
N003 B2 N004 116.7(3) . . ?
N003 B2 C00W 121.6(3) . . ?
N004 B2 C00W 121.6(3) . . ?
N001 B3 N002 116.5(3) . . ?
N001 B3 C00E 122.7(3) . . ?
N002 B3 C00E 120.7(3) . . ?
C00W C01A H01A 118.9 . . ?
C018 C01A C00W 122.2(3) . . ?
C018 C01A H01A 118.9 . . ?
C00D C01B H01B 120.3 . . ?
C00D C01B C01K 119.3(4) . . ?
C01K C01B H01B 120.3 . . ?
C00G C01C H01C 119.7 . . ?
C015 C01C C00G 120.6(3) . . ?
C015 C01C H01C 119.7 . . ?
C010 C01D H01D 119.4 . . ?
C010 C01D C01E 121.2(4) . . ?
C01E C01D H01D 119.4 . . ?
C00K C01E C01D 120.2(4) . . ?
C00K C01E H01E 119.9 . . ?
C01D C01E H01E 119.9 . . ?
C012 C01F H01F 119.7 . . ?
C01P C01F C012 120.6(4) . . ?
C01P C01F H01F 119.7 . . ?
C00H C01G H01G 119.9 . . ?
C00H C01G C01P 120.2(4) . . ?
C01P C01G H01G 119.9 . . ?
C00V C01H H01H 120.3 . . ?
C016 C01H C00V 119.3(3) . . ?
C016 C01H H01H 120.4 . . ?
C00N C01I H01I 119.7 . . ?
C01J C01I C00N 120.6(4) . . ?
C01J C01I H01I 119.7 . . ?
C019 C01J H01J 119.3 . . ?
C01I C01J C019 121.4(4) . . ?
C01I C01J H01J 119.3 . . ?
C01B C01K H01K 119.1 . . ?
C01L C01K C01B 121.8(4) . . ?
C01L C01K H01K 119.1 . . ?
C012 C01L H01L 119.7 . . ?
C01K C01L C012 120.6(4) . . ?
C01K C01L H01L 119.7 . . ?
C011 C01M H01M 118.8 . . ?
C01N C01M C011 122.5(3) . . ?
C01N C01M H01M 118.8 . . ?
C00X C01N H01N 120.2 . . ?
C01M C01N C00X 119.6(4) . . ?
C01M C01N H01N 120.2 . . ?
C01F C01P C01G 121.3(4) . . ?
C01F C01P H01P 119.4 . . ?
C01G C01P H01P 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N001 C009 C00Q C015 -179.7(3) . . . . ?
N002 C008 C00U C00Y 176.7(3) . . . . ?
N003 C00D C01B C01K 177.8(3) . . . . ?
N004 C00H C01G C01P -177.2(3) . . . . ?
N005 C00B C019 C01J 177.8(3) . . . . ?
N006 C00K C01E C01D -177.3(3) . . . . ?
C007 C008 C00U C00Y -1.3(5) . . . . ?
C007 C009 C00Q C015 -1.1(5) . . . . ?
C007 C00G C00O C00Y 0.2(5) . . . . ?
C007 C00G C01C C015 0.1(5) . . . . ?
C008 N002 B3 N001 1.1(5) . . . . ?
C008 N002 B3 C00E 178.0(3) . . . . ?
C008 C007 C009 N001 -0.3(4) . . . . ?
C008 C007 C009 C00Q -178.9(3) . . . . ?
C008 C007 C00G C00O -2.1(4) . . . . ?
C008 C007 C00G C01C 179.4(3) . . . . ?
C008 C00U C00Y C00O -0.6(5) . . . . ?
C009 N001 B3 N002 4.2(5) . . . . ?
C009 N001 B3 C00E -172.6(3) . . . . ?
C009 C007 C008 N002 5.1(4) . . . . ?
C009 C007 C008 C00U -176.8(3) . . . . ?
C009 C007 C00G C00O 177.4(3) . . . . ?
C009 C007 C00G C01C -1.2(4) . . . . ?
C009 C00Q C015 C01C 0.0(6) . . . . ?
C00A C00B C019 C01J -0.6(5) . . . . ?
C00A C00K C01E C01D 1.1(6) . . . . ?
C00A C00N C010 C01D 0.8(5) . . . . ?
C00A C00N C01I C01J -0.7(5) . . . . ?
C00B N005 B1 N006 -1.7(5) . . . . ?
C00B N005 B1 C011 174.3(3) . . . . ?
C00B C00A C00K N006 -2.4(5) . . . . ?
C00B C00A C00K C01E 179.1(3) . . . . ?
C00B C00A C00N C010 180.0(3) . . . . ?
C00B C00A C00N C01I -0.2(5) . . . . ?
C00B C019 C01J C01I -0.3(6) . . . . ?
C00C C00D C01B C01K -0.9(5) . . . . ?
C00C C00H C01G C01P 2.1(6) . . . . ?
C00C C012 C01F C01P 1.0(6) . . . . ?
C00C C012 C01L C01K -1.2(6) . . . . ?
C00D N003 B2 N004 -3.2(5) . . . . ?
C00D N003 B2 C00W 174.9(3) . . . . ?
C00D C00C C00H N004 -2.9(5) . . . . ?
C00D C00C C00H C01G 177.8(3) . . . . ?
C00D C00C C012 C01F -179.3(3) . . . . ?
C00D C00C C012 C01L 0.3(5) . . . . ?
C00D C01B C01K C01L -0.1(6) . . . . ?
C00E C00F C00L C00V -1.3(6) . . . . ?
C00E C016 C01H C00V -1.2(6) . . . . ?
C00F C00E C016 C01H -0.3(6) . . . . ?
C00F C00E B3 N001 -68.7(5) . . . . ?
C00F C00E B3 N002 114.6(4) . . . . ?
C00F C00L C00V C017 179.3(3) . . . . ?
C00F C00L C00V C01H -0.3(5) . . . . ?
C00G C007 C008 N002 -175.5(3) . . . . ?
C00G C007 C008 C00U 2.6(4) . . . . ?
C00G C007 C009 N001 -179.7(3) . . . . ?
C00G C007 C009 C00Q 1.7(5) . . . . ?
C00G C00O C00Y C00U 1.2(6) . . . . ?
C00H N004 B2 N003 2.8(5) . . . . ?
C00H N004 B2 C00W -175.3(3) . . . . ?
C00H C00C C00D N003 2.5(5) . . . . ?
C00H C00C C00D C01B -178.8(3) . . . . ?
C00H C00C C012 C01F 0.2(5) . . . . ?
C00H C00C C012 C01L 179.8(3) . . . . ?
C00H C01G C01P C01F -0.8(6) . . . . ?
C00I C018 C01A C00W 1.6(6) . . . . ?
C00J C00W B2 N003 34.3(5) . . . . ?
C00J C00W B2 N004 -147.7(4) . . . . ?
C00J C00W C01A C018 -0.8(6) . . . . ?
C00K N006 B1 N005 1.4(5) . . . . ?
C00K N006 B1 C011 -174.5(3) . . . . ?
C00K C00A C00B N005 2.2(5) . . . . ?
C00K C00A C00B C019 -179.3(3) . . . . ?
C00K C00A C00N C010 0.2(5) . . . . ?
C00K C00A C00N C01I 179.9(3) . . . . ?
C00L C00V C01H C016 1.5(6) . . . . ?
C00N C00A C00B N005 -177.6(3) . . . . ?
C00N C00A C00B C019 0.9(5) . . . . ?
C00N C00A C00K N006 177.4(3) . . . . ?
C00N C00A C00K C01E -1.1(5) . . . . ?
C00N C010 C01D C01E -0.7(6) . . . . ?
C00N C01I C01J C019 1.0(6) . . . . ?
C00O C00G C01C C015 -178.4(3) . . . . ?
C00P C00S C00X C014 -179.6(3) . . . . ?
C00P C00S C00X C01N -0.3(5) . . . . ?
C00P C011 B1 N005 38.1(5) . . . . ?
C00P C011 B1 N006 -146.2(4) . . . . ?
C00P C011 C01M C01N 0.5(6) . . . . ?
C00Q C015 C01C C00G 0.5(6) . . . . ?
C00S C00P C011 B1 -179.0(3) . . . . ?
C00S C00P C011 C01M -1.5(5) . . . . ?
C00S C00X C01N C01M -0.6(6) . . . . ?
C00W C00J C00Z C00I 1.0(5) . . . . ?
C00Z C00I C018 C01A -1.1(6) . . . . ?
C00Z C00J C00W B2 -179.3(3) . . . . ?
C00Z C00J C00W C01A -0.6(5) . . . . ?
C010 C00N C01I C01J 179.0(4) . . . . ?
C010 C01D C01E C00K -0.2(6) . . . . ?
C011 C00P C00S C00X 1.4(5) . . . . ?
C011 C01M C01N C00X 0.6(7) . . . . ?
C012 C00C C00D N003 -177.9(3) . . . . ?
C012 C00C C00D C01B 0.8(5) . . . . ?
C012 C00C C00H N004 177.5(3) . . . . ?
C012 C00C C00H C01G -1.8(5) . . . . ?
C012 C01F C01P C01G -0.8(7) . . . . ?
C013 C00I C00Z C00J 179.2(3) . . . . ?
C013 C00I C018 C01A 179.5(4) . . . . ?
C014 C00X C01N C01M 178.6(4) . . . . ?
C016 C00E C00F C00L 1.5(5) . . . . ?
C016 C00E B3 N001 111.1(4) . . . . ?
C016 C00E B3 N002 -65.5(4) . . . . ?
C017 C00V C01H C016 -178.1(4) . . . . ?
C018 C00I C00Z C00J -0.2(5) . . . . ?
B1 N005 C00B C00A -0.1(5) . . . . ?
B1 N005 C00B C019 -178.6(3) . . . . ?
B1 N006 C00K C00A 0.5(5) . . . . ?
B1 N006 C00K C01E 179.0(4) . . . . ?
B1 C011 C01M C01N 178.0(4) . . . . ?
B2 N003 C00D C00C 0.6(5) . . . . ?
B2 N003 C00D C01B -178.0(3) . . . . ?
B2 N004 C00H C00C 0.1(5) . . . . ?
B2 N004 C00H C01G 179.4(3) . . . . ?
B2 C00W C01A C018 178.0(4) . . . . ?
B3 N001 C009 C007 -4.6(5) . . . . ?
B3 N001 C009 C00Q 174.0(3) . . . . ?
B3 N002 C008 C007 -5.6(4) . . . . ?
B3 N002 C008 C00U 176.3(3) . . . . ?
B3 C00E C00F C00L -178.6(3) . . . . ?
B3 C00E C016 C01H 179.9(4) . . . . ?
C01A C00W B2 N003 -144.4(4) . . . . ?
C01A C00W B2 N004 33.6(5) . . . . ?
C01B C01K C01L C012 1.2(6) . . . . ?
C01C C00G C00O C00Y 178.7(3) . . . . ?
C01F C012 C01L C01K 178.4(4) . . . . ?
C01I C00N C010 C01D -179.0(4) . . . . ?
C01L C012 C01F C01P -178.6(4) . . . . ?
C01M C011 B1 N005 -139.4(4) . . . . ?
C01M C011 B1 N006 36.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
