# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_dy9b
_database_code_depnum_ccdc_archive 'CCDC 2101023'
loop_
_audit_author_name
_audit_author_address
'Dengtao Yang'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-09-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_dy9b                
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.594        306 Report
RESPONSE:  The intrisic bad quality of the crystals is the reson of this alert.
It has been impossible to avoid this problem despite many attepmts.
;
# end Validation Reply Form

_audit_creation_date             2020-11-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H13 B2 N'
_chemical_formula_sum            'C12 H13 B2 N'
_chemical_formula_weight         192.85
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.995(5)
_cell_length_b                   8.942(6)
_cell_length_c                   9.230(6)
_cell_angle_alpha                69.122(5)
_cell_angle_beta                 89.652(6)
_cell_angle_gamma                83.064(6)
_cell_volume                     535.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    558
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.814
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2289
_diffrn_reflns_point_group_measured_fraction_full 0.814
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.732
_diffrn_ambient_temperature      179.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.814
_diffrn_measured_fraction_theta_max 0.836
_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           30.0
_diffrn_source_power             1.5
_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                1080
_reflns_number_total             1574
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1574
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.075
_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)+(0.0581P)²+0.1377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Uiso: H1A(0.05) H1B(0.05) H1C(0.05) H2A(0.05) H2B(0.05)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2842(3) 0.8421(3) 1.0089(3) 0.0316(6) Uani 1 1 d . . . . .
C1 C 0.2801(4) 0.8577(3) 0.8462(3) 0.0311(7) Uani 1 1 d . . . . .
C2 C 0.2427(3) 1.0318(3) 0.7655(3) 0.0270(6) Uani 1 1 d . . . . .
C3 C 0.2262(4) 1.1217(3) 0.6077(3) 0.0354(7) Uani 1 1 d . . . . .
H3 H 0.2382 1.0695 0.5341 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1920(4) 1.2873(3) 0.5591(3) 0.0396(7) Uani 1 1 d . . . . .
H4 H 0.1807 1.3490 0.4511 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1737(4) 1.3668(3) 0.6656(3) 0.0393(7) Uani 1 1 d . . . . .
H5 H 0.1501 1.4812 0.6293 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1896(3) 1.2797(3) 0.8227(3) 0.0342(7) Uani 1 1 d . . . . .
H6 H 0.1769 1.3327 0.8956 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2252(3) 1.1111(3) 0.8725(3) 0.0288(6) Uani 1 1 d . . . . .
C8 C 0.2512(3) 0.9900(3) 1.0257(3) 0.0283(6) Uani 1 1 d . . . . .
C9 C 0.2488(4) 0.9979(3) 1.1737(3) 0.0348(7) Uani 1 1 d . . . . .
H9 H 0.2243 1.0992 1.1865 0.042 Uiso 1 1 calc R U . . .
C10 C 0.2821(4) 0.8580(4) 1.3010(3) 0.0416(8) Uani 1 1 d . . . . .
H10 H 0.2812 0.8620 1.4024 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3173(4) 0.7097(4) 1.2806(3) 0.0409(7) Uani 1 1 d . . . . .
H11 H 0.3413 0.6129 1.3686 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3176(4) 0.7026(3) 1.1345(3) 0.0359(7) Uani 1 1 d . . . . .
H12 H 0.3409 0.6016 1.1211 0.043 Uiso 1 1 calc R U . . .
B1 B 0.1709(5) 0.7301(5) 0.7978(5) 0.0435(9) Uani 1 1 d . . . . .
B2 B 0.4396(5) 0.7434(4) 0.7905(5) 0.0414(9) Uani 1 1 d . . . . .
H1A H 0.321(4) 0.650(3) 0.767(3) 0.050 Uiso 1 1 d . U . . .
H1B H 0.086(4) 0.784(3) 0.684(3) 0.050 Uiso 1 1 d . U . . .
H1C H 0.107(4) 0.637(3) 0.902(3) 0.050 Uiso 1 1 d . U . . .
H2A H 0.541(4) 0.658(3) 0.891(3) 0.050 Uiso 1 1 d . U . . .
H2B H 0.500(4) 0.807(3) 0.674(3) 0.050 Uiso 1 1 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
N1 C1 1.458(3) . ?
N1 C8 1.378(3) . ?
N1 C12 1.362(3) . ?
C1 C2 1.458(4) . ?
C1 B1 1.632(4) . ?
C1 B2 1.627(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.403(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.401(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.401(4) . ?
C7 C8 1.438(4) . ?
C8 C9 1.393(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.372(4) . ?
C12 H12 0.9500 . ?
B1 B2 1.897(5) . ?
B1 H1A 1.29(3) . ?
B1 H1B 1.13(3) . ?
B1 H1C 1.15(3) . ?
B2 H1A 1.32(3) . ?
B2 H2A 1.15(3) . ?
B2 H2B 1.13(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
C8 N1 C1 111.9(2) . . ?
C12 N1 C1 126.8(2) . . ?
C12 N1 C8 121.3(2) . . ?
N1 C1 B1 118.1(2) . . ?
N1 C1 B2 118.5(2) . . ?
C2 C1 N1 102.7(2) . . ?
C2 C1 B1 122.9(2) . . ?
C2 C1 B2 122.6(2) . . ?
B2 C1 B1 71.2(2) . . ?
C3 C2 C1 130.0(2) . . ?
C3 C2 C7 119.6(2) . . ?
C7 C2 C1 110.4(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.5(2) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C8 107.7(2) . . ?
C6 C7 C2 121.1(2) . . ?
C6 C7 C8 131.2(2) . . ?
N1 C8 C7 107.4(2) . . ?
N1 C8 C9 119.7(2) . . ?
C9 C8 C7 133.0(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
N1 C12 C11 119.3(3) . . ?
N1 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C1 B1 B2 54.27(17) . . ?
C1 B1 H1A 98.2(13) . . ?
C1 B1 H1B 114.7(14) . . ?
C1 B1 H1C 113.1(14) . . ?
B2 B1 H1A 44.0(12) . . ?
B2 B1 H1B 116.7(15) . . ?
B2 B1 H1C 121.0(14) . . ?
H1A B1 H1B 103.7(18) . . ?
H1A B1 H1C 104.3(19) . . ?
H1B B1 H1C 119(2) . . ?
C1 B2 B1 54.51(17) . . ?
C1 B2 H1A 97.2(12) . . ?
C1 B2 H2A 112.3(13) . . ?
C1 B2 H2B 113.9(13) . . ?
B1 B2 H1A 42.8(11) . . ?
B1 B2 H2A 119.8(15) . . ?
B1 B2 H2B 117.6(14) . . ?
H1A B2 H2A 104.2(18) . . ?
H1A B2 H2B 105.8(18) . . ?
H2A B2 H2B 120(2) . . ?

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
N1 C1 C2 C3 178.8(2) . . . . ?
N1 C1 C2 C7 -0.4(2) . . . . ?
N1 C1 B1 B2 -112.9(3) . . . . ?
N1 C1 B2 B1 112.4(3) . . . . ?
N1 C8 C9 C10 0.9(3) . . . . ?
C1 N1 C8 C7 -0.4(3) . . . . ?
C1 N1 C8 C9 179.6(2) . . . . ?
C1 N1 C12 C11 179.6(2) . . . . ?
C1 C2 C3 C4 -179.3(2) . . . . ?
C1 C2 C7 C6 179.7(2) . . . . ?
C1 C2 C7 C8 0.1(3) . . . . ?
C2 C1 B1 B2 117.2(3) . . . . ?
C2 C1 B2 B1 -117.6(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C7 C8 N1 0.2(2) . . . . ?
C2 C7 C8 C9 -179.9(2) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C3 C2 C7 C8 -179.1(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C5 C6 C7 C8 179.0(2) . . . . ?
C6 C7 C8 N1 -179.4(2) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C7 C8 C9 C10 -179.0(2) . . . . ?
C8 N1 C1 C2 0.5(2) . . . . ?
C8 N1 C1 B1 -138.2(2) . . . . ?
C8 N1 C1 B2 139.0(3) . . . . ?
C8 N1 C12 C11 0.4(3) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 N1 0.4(4) . . . . ?
C12 N1 C1 C2 -178.8(2) . . . . ?
C12 N1 C1 B1 42.5(3) . . . . ?
C12 N1 C1 B2 -40.3(4) . . . . ?
C12 N1 C8 C7 178.9(2) . . . . ?
C12 N1 C8 C9 -1.0(3) . . . . ?
B1 C1 C2 C3 -45.2(4) . . . . ?
B1 C1 C2 C7 135.7(3) . . . . ?
B2 C1 C2 C3 42.4(4) . . . . ?
B2 C1 C2 C7 -136.7(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
