# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

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

data_2isopropylborazaronaphthalene
_database_code_depnum_ccdc_archive 'CCDC 2471064'
loop_
_audit_author_name
_audit_author_address
'Maxime Siegler'
;Johns Hopkins University
United States of America
;
_audit_update_record             
;
2025-07-08 deposited with the CCDC.	2025-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 B N'
_chemical_formula_sum            'C11 H14 B N'
_chemical_formula_weight         171.04

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'

_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                   5.80606(12)
_cell_length_b                   7.55044(15)
_cell_length_c                   11.4439(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.1273(19)
_cell_angle_gamma                90
_cell_volume                     498.815(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    110.00(10)
_cell_measurement_reflns_used    7165
_cell_measurement_theta_min      3.8760
_cell_measurement_theta_max      72.0660

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    0.486
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.498
_oxdiff_exptl_absorpt_empirical_full_max 1.626
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110.00(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            10074
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.885
_diffrn_reflns_theta_max         71.812
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1904
_reflns_number_gt                1857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.966

_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+0.0374P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 823 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.25(19)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1904
_refine_ls_number_parameters     124
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.090
_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
C1 C 0.0379(3) 0.3938(2) 0.28984(14) 0.0312(4) Uani 1 1 d . . . . .
H1 H -0.068456 0.359041 0.225019 0.037 Uiso 1 1 calc R U . . .
C2 C -0.0085(2) 0.3584(2) 0.40064(14) 0.0288(3) Uani 1 1 d . . . . .
H2 H -0.149551 0.300583 0.412296 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1495(2) 0.40572(19) 0.50197(13) 0.0259(3) Uani 1 1 d . . . . .
C4 C 0.1020(3) 0.3664(2) 0.61729(14) 0.0296(4) Uani 1 1 d . . . . .
H4 H -0.038854 0.308600 0.629304 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2558(3) 0.4102(2) 0.71307(14) 0.0332(4) Uani 1 1 d . . . . .
H5 H 0.220595 0.383313 0.790285 0.040 Uiso 1 1 calc R U . . .
C6 C 0.4645(3) 0.4947(2) 0.69593(14) 0.0325(4) Uani 1 1 d . . . . .
H6 H 0.571091 0.524508 0.761799 0.039 Uiso 1 1 calc R U . . .
C7 C 0.5161(2) 0.5348(2) 0.58413(14) 0.0278(3) Uani 1 1 d . . . . .
H7 H 0.658099 0.591960 0.573440 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3602(2) 0.4917(2) 0.48604(13) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.3356(3) 0.5425(2) 0.14376(14) 0.0332(4) Uani 1 1 d . . . . .
H9 H 0.472831 0.622990 0.155505 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1390(3) 0.6401(3) 0.07026(17) 0.0484(5) Uani 1 1 d . . . . .
H10A H 0.182885 0.660983 -0.008946 0.073 Uiso 1 1 calc R U . . .
H10B H 0.110604 0.753844 0.107441 0.073 Uiso 1 1 calc R U . . .
H10C H -0.002018 0.568046 0.065276 0.073 Uiso 1 1 calc R U . . .
C11 C 0.4035(3) 0.3775(3) 0.07769(14) 0.0408(4) Uani 1 1 d . . . . .
H11A H 0.271581 0.296025 0.067001 0.061 Uiso 1 1 calc R U . . .
H11B H 0.534442 0.318707 0.123055 0.061 Uiso 1 1 calc R U . . .
H11C H 0.448034 0.412221 0.000694 0.061 Uiso 1 1 calc R U . . .
B1 B 0.2623(3) 0.4900(2) 0.26875(15) 0.0289(4) Uani 1 1 d . . . . .
N1 N 0.4078(2) 0.53246(16) 0.37277(11) 0.0260(3) Uani 1 1 d D . . . .
H1N H 0.537(3) 0.590(3) 0.3700(16) 0.031 Uiso 1 1 d D 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
C1 C2 1.351(2) . ?
C1 B1 1.533(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.444(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(2) . ?
C3 C8 1.414(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(2) . ?
C7 H7 0.9500 . ?
C8 N1 1.3884(18) . ?
C9 C11 1.530(2) . ?
C9 C10 1.532(2) . ?
C9 B1 1.585(2) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
B1 N1 1.421(2) . ?
N1 H1N 0.871(18) . ?

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
C2 C1 B1 119.95(14) . . ?
C2 C1 H1 120.0 . . ?
B1 C1 H1 120.0 . . ?
C1 C2 C3 122.12(14) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C8 118.43(14) . . ?
C4 C3 C2 121.96(14) . . ?
C8 C3 C2 119.60(14) . . ?
C5 C4 C3 121.32(14) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.63(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.45(15) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.39(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
N1 C8 C7 121.32(13) . . ?
N1 C8 C3 118.90(13) . . ?
C7 C8 C3 119.78(13) . . ?
C11 C9 C10 109.66(14) . . ?
C11 C9 B1 110.53(14) . . ?
C10 C9 B1 111.08(13) . . ?
C11 C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
B1 C9 H9 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 B1 C1 114.46(14) . . ?
N1 B1 C9 120.46(14) . . ?
C1 B1 C9 125.07(14) . . ?
C8 N1 B1 124.93(13) . . ?
C8 N1 H1N 113.7(12) . . ?
B1 N1 H1N 121.3(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 C4 -179.10(14) . . . . ?
C1 C2 C3 C8 -0.1(2) . . . . ?
C8 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C5 179.10(13) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 N1 179.35(13) . . . . ?
C6 C7 C8 C3 -0.3(2) . . . . ?
C4 C3 C8 N1 -179.42(15) . . . . ?
C2 C3 C8 N1 1.52(19) . . . . ?
C4 C3 C8 C7 0.28(19) . . . . ?
C2 C3 C8 C7 -178.78(15) . . . . ?
C2 C1 B1 N1 0.8(2) . . . . ?
C2 C1 B1 C9 -178.87(15) . . . . ?
C11 C9 B1 N1 108.65(17) . . . . ?
C10 C9 B1 N1 -129.38(17) . . . . ?
C11 C9 B1 C1 -71.66(19) . . . . ?
C10 C9 B1 C1 50.3(2) . . . . ?
C7 C8 N1 B1 178.48(14) . . . . ?
C3 C8 N1 B1 -1.8(2) . . . . ?
C1 B1 N1 C8 0.7(2) . . . . ?
C9 B1 N1 C8 -179.63(12) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_N-benzyl_2_isopropylborazaronaphthalene
_database_code_depnum_ccdc_archive 'CCDC 2471066'
loop_
_audit_author_name
_audit_author_address
'Maxime Siegler'
;Johns Hopkins University
United States of America
;
_audit_update_record             
;
2025-07-08 deposited with the CCDC.	2025-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 B N'
_chemical_formula_sum            'C18 H20 B N'
_chemical_formula_weight         261.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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'

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

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

_cell_length_a                   9.63386(7)
_cell_length_b                   8.72627(8)
_cell_length_c                   36.3137(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3052.81(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    243.00(10)
_cell_measurement_reflns_used    17872
_cell_measurement_theta_min      2.4260
_cell_measurement_theta_max      72.1040

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.281
_exptl_absorpt_coefficient_mu    0.484
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.735
_oxdiff_exptl_absorpt_empirical_full_max 1.263
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      243.00(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            32666
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.433
_diffrn_reflns_theta_max         71.900
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2988
_reflns_number_gt                2794
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+0.6505P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.52924(15) 0.60667(18) 0.54799(3) 0.0605(4) Uani 1 1 d . . . . .
H1 H 0.541154 0.650997 0.524613 0.073 Uiso 1 1 calc R U . . .
C2 C 0.60049(14) 0.48035(18) 0.55695(4) 0.0611(4) Uani 1 1 d . . . . .
H2 H 0.660525 0.436645 0.539450 0.073 Uiso 1 1 calc R U . . .
C3 C 0.58792(12) 0.40982(15) 0.59241(4) 0.0532(3) Uani 1 1 d . . . . .
C4 C 0.66639(14) 0.27959(17) 0.60162(4) 0.0665(4) Uani 1 1 d . . . . .
H4 H 0.727934 0.238738 0.584096 0.080 Uiso 1 1 calc R U . . .
C5 C 0.65595(16) 0.21049(18) 0.63530(5) 0.0710(4) Uani 1 1 d . . . . .
H5 H 0.709603 0.123577 0.640892 0.085 Uiso 1 1 calc R U . . .
C6 C 0.56495(15) 0.27073(18) 0.66105(4) 0.0666(4) Uani 1 1 d . . . . .
H6 H 0.556863 0.223953 0.684266 0.080 Uiso 1 1 calc R U . . .
C7 C 0.48631(14) 0.39800(16) 0.65311(4) 0.0569(3) Uani 1 1 d . . . . .
H7 H 0.425557 0.437040 0.671065 0.068 Uiso 1 1 calc R U . . .
C8 C 0.49499(12) 0.47056(14) 0.61880(3) 0.0479(3) Uani 1 1 d . . . . .
C9 C 0.31279(13) 0.64804(16) 0.63776(3) 0.0535(3) Uani 1 1 d . . . . .
H9A H 0.261489 0.557195 0.645910 0.064 Uiso 1 1 calc R U . . .
H9B H 0.246120 0.717449 0.626038 0.064 Uiso 1 1 calc R U . . .
C10 C 0.37247(13) 0.72709(15) 0.67132(3) 0.0516(3) Uani 1 1 d . . . . .
C11 C 0.49540(15) 0.80855(17) 0.67019(4) 0.0597(3) Uani 1 1 d . . . . .
H11 H 0.546412 0.812754 0.648148 0.072 Uiso 1 1 calc R U . . .
C12 C 0.54446(19) 0.88415(18) 0.70113(4) 0.0719(4) Uani 1 1 d . . . . .
H12 H 0.628192 0.939234 0.699945 0.086 Uiso 1 1 calc R U . . .
C13 C 0.4707(2) 0.8787(2) 0.73363(4) 0.0835(5) Uani 1 1 d . . . . .
H13 H 0.503440 0.930500 0.754602 0.100 Uiso 1 1 calc R U . . .
C14 C 0.3488(2) 0.7967(3) 0.73508(4) 0.0878(6) Uani 1 1 d . . . . .
H14 H 0.298286 0.792201 0.757206 0.105 Uiso 1 1 calc R U . . .
C15 C 0.30006(16) 0.7212(2) 0.70432(4) 0.0694(4) Uani 1 1 d . . . . .
H15 H 0.216902 0.665211 0.705720 0.083 Uiso 1 1 calc R U . . .
C16 C 0.35203(17) 0.83492(18) 0.56615(4) 0.0658(4) Uani 1 1 d . . . . .
H16 H 0.278482 0.851182 0.584786 0.079 Uiso 1 1 calc R U . . .
C17 C 0.4531(3) 0.9651(2) 0.56887(7) 0.1263(10) Uani 1 1 d . . . . .
H17A H 0.526564 0.951061 0.550904 0.189 Uiso 1 1 calc R U . . .
H17B H 0.492835 0.967617 0.593410 0.189 Uiso 1 1 calc R U . . .
H17C H 0.405439 1.060952 0.564049 0.189 Uiso 1 1 calc R U . . .
C18 C 0.2849(2) 0.8359(2) 0.52850(5) 0.0983(6) Uani 1 1 d . . . . .
H18A H 0.236240 0.932057 0.524905 0.147 Uiso 1 1 calc R U . . .
H18B H 0.219627 0.751622 0.526714 0.147 Uiso 1 1 calc R U . . .
H18C H 0.355854 0.824693 0.509736 0.147 Uiso 1 1 calc R U . . .
B1 B 0.42869(15) 0.67947(19) 0.57545(4) 0.0531(4) Uani 1 1 d . . . . .
N1 N 0.41530(10) 0.60035(12) 0.60997(3) 0.0477(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.339(2) . ?
C1 B1 1.5285(19) . ?
C1 H1 0.9400 . ?
C2 C3 1.4325(19) . ?
C2 H2 0.9400 . ?
C3 C4 1.405(2) . ?
C3 C8 1.4144(16) . ?
C4 C5 1.367(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.375(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.4002(18) . ?
C7 H7 0.9400 . ?
C8 N1 1.4054(16) . ?
C9 N1 1.4719(14) . ?
C9 C10 1.5139(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.382(2) . ?
C10 C15 1.3874(17) . ?
C11 C12 1.3859(19) . ?
C11 H11 0.9400 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.379(2) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 C17 1.500(3) . ?
C16 C18 1.512(2) . ?
C16 B1 1.581(2) . ?
C16 H16 0.9900 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
B1 N1 1.4368(18) . ?

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
C2 C1 B1 120.58(13) . . ?
C2 C1 H1 119.7 . . ?
B1 C1 H1 119.7 . . ?
C1 C2 C3 121.92(12) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C8 118.84(13) . . ?
C4 C3 C2 121.05(12) . . ?
C8 C3 C2 120.11(12) . . ?
C5 C4 C3 122.00(13) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 118.88(14) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.92(14) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.26(13) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 N1 122.34(11) . . ?
C7 C8 C3 118.11(12) . . ?
N1 C8 C3 119.55(11) . . ?
N1 C9 C10 115.21(10) . . ?
N1 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
N1 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C15 118.39(13) . . ?
C11 C10 C9 122.41(11) . . ?
C15 C10 C9 119.18(13) . . ?
C10 C11 C12 120.87(13) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.13(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.38(15) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.49(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.73(16) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 C18 109.44(16) . . ?
C17 C16 B1 109.42(14) . . ?
C18 C16 B1 113.44(13) . . ?
C17 C16 H16 108.1 . . ?
C18 C16 H16 108.1 . . ?
B1 C16 H16 108.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 B1 C1 115.23(13) . . ?
N1 B1 C16 123.83(12) . . ?
C1 B1 C16 120.88(12) . . ?
C8 N1 B1 122.50(10) . . ?
C8 N1 C9 115.97(10) . . ?
B1 N1 C9 121.49(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 C4 -178.29(13) . . . . ?
C1 C2 C3 C8 2.0(2) . . . . ?
C8 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 C5 -179.98(14) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 N1 179.73(12) . . . . ?
C6 C7 C8 C3 -0.38(19) . . . . ?
C4 C3 C8 C7 0.38(17) . . . . ?
C2 C3 C8 C7 -179.91(12) . . . . ?
C4 C3 C8 N1 -179.72(11) . . . . ?
C2 C3 C8 N1 -0.01(17) . . . . ?
N1 C9 C10 C11 27.39(18) . . . . ?
N1 C9 C10 C15 -154.22(13) . . . . ?
C15 C10 C11 C12 -0.8(2) . . . . ?
C9 C10 C11 C12 177.65(13) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C11 C10 C15 C14 0.9(2) . . . . ?
C9 C10 C15 C14 -177.57(14) . . . . ?
C2 C1 B1 N1 -1.67(19) . . . . ?
C2 C1 B1 C16 175.73(13) . . . . ?
C17 C16 B1 N1 103.27(18) . . . . ?
C18 C16 B1 N1 -134.22(16) . . . . ?
C17 C16 B1 C1 -73.90(19) . . . . ?
C18 C16 B1 C1 48.6(2) . . . . ?
C7 C8 N1 B1 176.96(12) . . . . ?
C3 C8 N1 B1 -2.93(17) . . . . ?
C7 C8 N1 C9 -5.16(16) . . . . ?
C3 C8 N1 C9 174.95(10) . . . . ?
C1 B1 N1 C8 3.68(17) . . . . ?
C16 B1 N1 C8 -173.63(12) . . . . ?
C1 B1 N1 C9 -174.08(11) . . . . ?
C16 B1 N1 C9 8.60(19) . . . . ?
C10 C9 N1 C8 75.00(14) . . . . ?
C10 C9 N1 B1 -107.09(13) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.024

####################################################################### 
# 
# 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_N_benzyl_2_chloromethyl_borazaronaphthalene
_database_code_depnum_ccdc_archive 'CCDC 2471065'
loop_
_audit_author_name
_audit_author_address
'Maxime Siegler'
;Johns Hopkins University
United States of America
;
_audit_update_record             
;
2025-07-08 deposited with the CCDC.	2025-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 B Cl N'
_chemical_formula_sum            'C16 H15 B Cl N'
_chemical_formula_weight         267.55

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.15626(17)
_cell_length_b                   8.98468(18)
_cell_length_c                   11.7166(2)
_cell_angle_alpha                100.8560(17)
_cell_angle_beta                 93.9083(17)
_cell_angle_gamma                108.2052(19)
_cell_volume                     793.58(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    110.00(10)
_cell_measurement_reflns_used    17540
_cell_measurement_theta_min      3.8630
_cell_measurement_theta_max      72.0940

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
#
# there is a red colored deposit on the surface of the crystals,
# but when crushed the crystals are colorless.
#
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    1.992
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.553
_oxdiff_exptl_absorpt_empirical_full_max 2.154
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110.00(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            25296
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.877
_diffrn_reflns_theta_max         71.873
_diffrn_reflns_theta_full        67.679
_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             3103
_reflns_number_gt                3047
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+0.4231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3103
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.81075(17) 0.53953(16) 0.10809(12) 0.0228(3) Uani 1 1 d . . . . .
H1 H 0.915930 0.526622 0.085295 0.027 Uiso 1 1 calc R U . . .
C2 C 0.80053(17) 0.68769(16) 0.14611(12) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.900086 0.778882 0.148849 0.027 Uiso 1 1 calc R U . . .
C3 C 0.64443(17) 0.71203(15) 0.18250(11) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.63959(18) 0.86833(16) 0.22427(12) 0.0247(3) Uani 1 1 d . . . . .
H4 H 0.740810 0.957982 0.227013 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4926(2) 0.89438(17) 0.26104(13) 0.0278(3) Uani 1 1 d . . . . .
H5 H 0.492332 1.000484 0.289719 0.033 Uiso 1 1 calc R U . . .
C6 C 0.34319(19) 0.76191(18) 0.25555(13) 0.0285(3) Uani 1 1 d . . . . .
H6 H 0.240406 0.778764 0.279861 0.034 Uiso 1 1 calc R U . . .
C7 C 0.34291(18) 0.60750(17) 0.21545(12) 0.0250(3) Uani 1 1 d . . . . .
H7 H 0.240438 0.519340 0.213280 0.030 Uiso 1 1 calc R U . . .
C8 C 0.49235(16) 0.57883(15) 0.17773(11) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.33714(16) 0.28834(15) 0.13460(11) 0.0200(3) Uani 1 1 d . . . . .
H9A H 0.338770 0.193834 0.076093 0.024 Uiso 1 1 calc R U . . .
H9B H 0.235489 0.317340 0.108389 0.024 Uiso 1 1 calc R U . . .
C10 C 0.31331(16) 0.24151(15) 0.25180(11) 0.0196(3) Uani 1 1 d . . . . .
C11 C 0.43233(18) 0.31795(16) 0.35252(12) 0.0252(3) Uani 1 1 d . . . . .
H11 H 0.532142 0.406646 0.350536 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4063(2) 0.26541(18) 0.45627(13) 0.0310(3) Uani 1 1 d . . . . .
H12 H 0.488320 0.318607 0.524744 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2617(2) 0.13624(19) 0.46044(13) 0.0319(3) Uani 1 1 d . . . . .
H13 H 0.244779 0.100200 0.531320 0.038 Uiso 1 1 calc R U . . .
C14 C 0.14184(19) 0.05979(18) 0.36054(13) 0.0296(3) Uani 1 1 d . . . . .
H14 H 0.042057 -0.028708 0.362907 0.036 Uiso 1 1 calc R U . . .
C15 C 0.16728(17) 0.11225(17) 0.25710(12) 0.0247(3) Uani 1 1 d . . . . .
H15 H 0.084253 0.059517 0.189042 0.030 Uiso 1 1 calc R U . . .
C16 C 0.64169(17) 0.21187(16) 0.06136(12) 0.0231(3) Uani 1 1 d . . . . .
H16A H 0.561971 0.163004 -0.013294 0.028 Uiso 1 1 calc R U . . .
H16B H 0.592016 0.151954 0.120684 0.028 Uiso 1 1 calc R U . . .
B1 B 0.65010(19) 0.39373(18) 0.10257(13) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.49679(14) 0.42312(12) 0.13676(9) 0.0190(2) Uani 1 1 d . . . . .
Cl1 Cl 0.85063(4) 0.18946(4) 0.04056(3) 0.03308(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3521(19) . ?
C1 B1 1.5235(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.4366(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.4112(19) . ?
C3 C8 1.4184(18) . ?
C4 C5 1.373(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.4050(19) . ?
C7 H7 0.9500 . ?
C8 N1 1.4036(17) . ?
C9 N1 1.4702(15) . ?
C9 C10 1.5176(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3887(18) . ?
C10 C15 1.3943(18) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3865(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 B1 1.5925(19) . ?
C16 Cl1 1.8046(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
B1 N1 1.4242(18) . ?

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
C2 C1 B1 118.63(12) . . ?
C2 C1 H1 120.7 . . ?
B1 C1 H1 120.7 . . ?
C1 C2 C3 122.31(12) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C8 118.77(12) . . ?
C4 C3 C2 120.80(12) . . ?
C8 C3 C2 120.43(12) . . ?
C5 C4 C3 121.81(13) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.86(13) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 121.02(13) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.80(13) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N1 C8 C7 122.30(12) . . ?
N1 C8 C3 118.97(11) . . ?
C7 C8 C3 118.73(12) . . ?
N1 C9 C10 114.24(10) . . ?
N1 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
N1 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C15 118.74(12) . . ?
C11 C10 C9 123.16(11) . . ?
C15 C10 C9 118.07(11) . . ?
C10 C11 C12 120.39(13) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.47(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.53(13) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.11(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.76(13) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
B1 C16 Cl1 113.74(9) . . ?
B1 C16 H16A 108.8 . . ?
Cl1 C16 H16A 108.8 . . ?
B1 C16 H16B 108.8 . . ?
Cl1 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
N1 B1 C1 117.30(12) . . ?
N1 B1 C16 117.97(11) . . ?
C1 B1 C16 124.73(12) . . ?
C8 N1 B1 122.33(11) . . ?
C8 N1 C9 117.26(10) . . ?
B1 N1 C9 120.37(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 C1 C2 C3 0.7(2) . . . . ?
C1 C2 C3 C4 178.53(12) . . . . ?
C1 C2 C3 C8 -1.1(2) . . . . ?
C8 C3 C4 C5 0.53(19) . . . . ?
C2 C3 C4 C5 -179.08(12) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 N1 179.77(12) . . . . ?
C6 C7 C8 C3 0.5(2) . . . . ?
C4 C3 C8 N1 -179.71(11) . . . . ?
C2 C3 C8 N1 -0.10(18) . . . . ?
C4 C3 C8 C7 -0.39(18) . . . . ?
C2 C3 C8 C7 179.22(12) . . . . ?
N1 C9 C10 C11 -0.55(18) . . . . ?
N1 C9 C10 C15 -178.53(11) . . . . ?
C15 C10 C11 C12 0.4(2) . . . . ?
C9 C10 C11 C12 -177.56(13) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C10 0.3(2) . . . . ?
C11 C10 C15 C14 -0.6(2) . . . . ?
C9 C10 C15 C14 177.48(13) . . . . ?
C2 C1 B1 N1 0.81(19) . . . . ?
C2 C1 B1 C16 -179.25(12) . . . . ?
Cl1 C16 B1 N1 -171.60(10) . . . . ?
Cl1 C16 B1 C1 8.46(17) . . . . ?
C7 C8 N1 B1 -177.64(12) . . . . ?
C3 C8 N1 B1 1.66(18) . . . . ?
C7 C8 N1 C9 -0.05(17) . . . . ?
C3 C8 N1 C9 179.24(10) . . . . ?
C1 B1 N1 C8 -2.00(18) . . . . ?
C16 B1 N1 C8 178.05(11) . . . . ?
C1 B1 N1 C9 -179.51(11) . . . . ?
C16 B1 N1 C9 0.54(17) . . . . ?
C10 C9 N1 C8 -81.87(14) . . . . ?
C10 C9 N1 B1 95.77(14) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.039


