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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_test_a
_database_code_depnum_ccdc_archive 'CCDC 2130024'
loop_
_audit_author_name
_audit_author_address
'Jonas Bachmann'
;JMU Wuerzburg
Germany
;
_audit_update_record             
;
2021-12-20 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_audit_creation_date             2021-12-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H23 B Cl N Si'
_chemical_formula_sum            'C13 H23 B Cl N Si'
_chemical_formula_weight         267.67
_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'
Si Si 0.0817 0.0704 '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'

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

_cell_length_a                   8.256(4)
_cell_length_b                   11.579(6)
_cell_length_c                   16.616(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.076(15)
_cell_angle_gamma                90
_cell_volume                     1547.3(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5622
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7122
_exptl_absorpt_correction_T_min  0.5340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1560 before and 0.1185 after correction.
The Ratio of minimum to maximum transmission is 0.7498.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.170
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14118
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         2.163
_diffrn_ambient_temperature      98.42
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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                   'rotating-anode X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_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                2693
_reflns_number_total             3160
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1501P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1954
_refine_ls_wR_factor_ref         0.2042
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C2(H2a,H2b,H2c), C3(H3a,H3b,H3c), C4(H4a,H4b,H4c), C7(H7a,
 H7b,H7c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1_1 Cl 0.91718(7) 0.82966(6) 0.61782(4) 0.0264(3) Uani 1 1 d . . . . .
Si1_1 Si 0.89392(8) 0.71633(5) 0.43266(4) 0.0154(3) Uani 1 1 d . . . . .
N1_1 N 0.7390(2) 0.69355(17) 0.49168(12) 0.0155(4) Uani 1 1 d . . . . .
B1_1 B 0.7453(3) 0.7364(2) 0.57067(17) 0.0169(6) Uani 1 1 d . . . . .
C1_1 C 0.5921(3) 0.6241(2) 0.45193(15) 0.0218(6) Uani 1 1 d . . . . .
H1A_1 H 0.515893 0.618346 0.489228 0.033 Uiso 1 1 calc R U . . .
H1B_1 H 0.627959 0.546589 0.439910 0.033 Uiso 1 1 calc R U . . .
H1C_1 H 0.535088 0.661458 0.400352 0.033 Uiso 1 1 calc R U . . .
C2_1 C 0.8284(3) 0.6349(2) 0.33396(16) 0.0222(6) Uani 1 1 d . . . . .
H2A_1 H 0.816234 0.552955 0.345992 0.033 Uiso 1 1 calc R U . . .
H2B_1 H 0.912737 0.643833 0.301308 0.033 Uiso 1 1 calc R U . . .
H2C_1 H 0.721873 0.665210 0.302660 0.033 Uiso 1 1 calc R U . . .
C3_1 C 1.0989(3) 0.6586(2) 0.48956(17) 0.0254(6) Uani 1 1 d . . . . .
H3A_1 H 1.131285 0.696136 0.543666 0.038 Uiso 1 1 calc R U . . .
H3B_1 H 1.183082 0.674152 0.457767 0.038 Uiso 1 1 calc R U . . .
H3C_1 H 1.090092 0.575040 0.497113 0.038 Uiso 1 1 calc R U . . .
C4_1 C 0.9083(4) 0.8723(2) 0.40852(17) 0.0273(6) Uani 1 1 d . . . . .
H4A_1 H 0.800464 0.899350 0.376388 0.041 Uiso 1 1 calc R U . . .
H4B_1 H 0.992989 0.883429 0.376356 0.041 Uiso 1 1 calc R U . . .
H4C_1 H 0.938960 0.916368 0.460089 0.041 Uiso 1 1 calc R U . . .
C1_2 C 0.6165(3) 0.7126(2) 0.62614(15) 0.0166(5) Uani 1 1 d . . . . .
C2_2 C 0.4852(3) 0.7908(2) 0.62637(15) 0.0174(5) Uani 1 1 d . . . . .
C3_2 C 0.3777(3) 0.7720(2) 0.67938(15) 0.0195(6) Uani 1 1 d . . . . .
H3_2 H 0.291282 0.826000 0.679785 0.023 Uiso 1 1 calc R U . . .
C4_2 C 0.3937(3) 0.6769(2) 0.73118(15) 0.0201(5) Uani 1 1 d . . . . .
C5_2 C 0.5223(3) 0.5992(2) 0.72998(15) 0.0194(5) Uani 1 1 d . . . . .
H5_2 H 0.534696 0.533103 0.764708 0.023 Uiso 1 1 calc R U . . .
C6_2 C 0.6336(3) 0.6164(2) 0.67872(15) 0.0178(5) Uani 1 1 d . . . . .
C7_2 C 0.4589(3) 0.8924(2) 0.56838(17) 0.0258(6) Uani 1 1 d . . . . .
H7A_2 H 0.356268 0.932509 0.571916 0.039 Uiso 1 1 calc R U . . .
H7B_2 H 0.450268 0.865277 0.511695 0.039 Uiso 1 1 calc R U . . .
H7C_2 H 0.553227 0.945568 0.583785 0.039 Uiso 1 1 calc R U . . .
C8_2 C 0.2754(3) 0.6572(2) 0.78757(17) 0.0291(7) Uani 1 1 d . . . . .
H8A_2 H 0.331452 0.676350 0.844507 0.044 Uiso 1 1 calc R U . . .
H8B_2 H 0.241145 0.575957 0.784643 0.044 Uiso 1 1 calc R U . . .
H8C_2 H 0.177249 0.706410 0.770016 0.044 Uiso 1 1 calc R U . . .
C9_2 C 0.7731(3) 0.5305(2) 0.68029(16) 0.0250(6) Uani 1 1 d . . . . .
H9A_2 H 0.772411 0.472398 0.723110 0.037 Uiso 1 1 calc R U . . .
H9B_2 H 0.880019 0.571099 0.692398 0.037 Uiso 1 1 calc R U . . .
H9C_2 H 0.756974 0.492433 0.626373 0.037 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
Cl1_1 B1_1 1.814(3) . ?
Si1_1 N1_1 1.798(2) . ?
Si1_1 C2_1 1.862(3) . ?
Si1_1 C3_1 1.866(3) . ?
Si1_1 C4_1 1.860(3) . ?
N1_1 B1_1 1.393(4) . ?
N1_1 C1_1 1.481(3) . ?
B1_1 C1_2 1.581(3) . ?
C1_1 H1A_1 0.9800 . ?
C1_1 H1B_1 0.9800 . ?
C1_1 H1C_1 0.9800 . ?
C2_1 H2A_1 0.9800 . ?
C2_1 H2B_1 0.9800 . ?
C2_1 H2C_1 0.9800 . ?
C3_1 H3A_1 0.9800 . ?
C3_1 H3B_1 0.9800 . ?
C3_1 H3C_1 0.9800 . ?
C4_1 H4A_1 0.9800 . ?
C4_1 H4B_1 0.9800 . ?
C4_1 H4C_1 0.9800 . ?
C1_2 C2_2 1.413(3) . ?
C1_2 C6_2 1.403(4) . ?
C2_2 C3_2 1.402(3) . ?
C2_2 C7_2 1.505(3) . ?
C3_2 H3_2 0.9500 . ?
C3_2 C4_2 1.385(4) . ?
C4_2 C5_2 1.396(3) . ?
C4_2 C8_2 1.515(3) . ?
C5_2 H5_2 0.9500 . ?
C5_2 C6_2 1.402(3) . ?
C6_2 C9_2 1.518(3) . ?
C7_2 H7A_2 0.9800 . ?
C7_2 H7B_2 0.9800 . ?
C7_2 H7C_2 0.9800 . ?
C8_2 H8A_2 0.9800 . ?
C8_2 H8B_2 0.9800 . ?
C8_2 H8C_2 0.9800 . ?
C9_2 H9A_2 0.9800 . ?
C9_2 H9B_2 0.9800 . ?
C9_2 H9C_2 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1_1 Si1_1 C2_1 107.78(11) . . ?
N1_1 Si1_1 C3_1 110.28(11) . . ?
N1_1 Si1_1 C4_1 110.36(11) . . ?
C2_1 Si1_1 C3_1 108.30(12) . . ?
C4_1 Si1_1 C2_1 108.75(13) . . ?
C4_1 Si1_1 C3_1 111.26(13) . . ?
B1_1 N1_1 Si1_1 125.59(17) . . ?
B1_1 N1_1 C1_1 117.8(2) . . ?
C1_1 N1_1 Si1_1 116.65(15) . . ?
N1_1 B1_1 Cl1_1 118.54(19) . . ?
N1_1 B1_1 C1_2 126.9(2) . . ?
C1_2 B1_1 Cl1_1 114.55(18) . . ?
N1_1 C1_1 H1A_1 109.5 . . ?
N1_1 C1_1 H1B_1 109.5 . . ?
N1_1 C1_1 H1C_1 109.5 . . ?
H1A_1 C1_1 H1B_1 109.5 . . ?
H1A_1 C1_1 H1C_1 109.5 . . ?
H1B_1 C1_1 H1C_1 109.5 . . ?
Si1_1 C2_1 H2A_1 109.5 . . ?
Si1_1 C2_1 H2B_1 109.5 . . ?
Si1_1 C2_1 H2C_1 109.5 . . ?
H2A_1 C2_1 H2B_1 109.5 . . ?
H2A_1 C2_1 H2C_1 109.5 . . ?
H2B_1 C2_1 H2C_1 109.5 . . ?
Si1_1 C3_1 H3A_1 109.5 . . ?
Si1_1 C3_1 H3B_1 109.5 . . ?
Si1_1 C3_1 H3C_1 109.5 . . ?
H3A_1 C3_1 H3B_1 109.5 . . ?
H3A_1 C3_1 H3C_1 109.5 . . ?
H3B_1 C3_1 H3C_1 109.5 . . ?
Si1_1 C4_1 H4A_1 109.5 . . ?
Si1_1 C4_1 H4B_1 109.5 . . ?
Si1_1 C4_1 H4C_1 109.5 . . ?
H4A_1 C4_1 H4B_1 109.5 . . ?
H4A_1 C4_1 H4C_1 109.5 . . ?
H4B_1 C4_1 H4C_1 109.5 . . ?
C2_2 C1_2 B1_1 120.5(2) . . ?
C6_2 C1_2 B1_1 121.0(2) . . ?
C6_2 C1_2 C2_2 118.4(2) . . ?
C1_2 C2_2 C7_2 119.9(2) . . ?
C3_2 C2_2 C1_2 119.8(2) . . ?
C3_2 C2_2 C7_2 120.3(2) . . ?
C2_2 C3_2 H3_2 119.0 . . ?
C4_2 C3_2 C2_2 121.9(2) . . ?
C4_2 C3_2 H3_2 119.0 . . ?
C3_2 C4_2 C5_2 118.0(2) . . ?
C3_2 C4_2 C8_2 121.3(2) . . ?
C5_2 C4_2 C8_2 120.7(2) . . ?
C4_2 C5_2 H5_2 119.2 . . ?
C4_2 C5_2 C6_2 121.5(2) . . ?
C6_2 C5_2 H5_2 119.2 . . ?
C1_2 C6_2 C9_2 120.0(2) . . ?
C5_2 C6_2 C1_2 120.3(2) . . ?
C5_2 C6_2 C9_2 119.7(2) . . ?
C2_2 C7_2 H7A_2 109.5 . . ?
C2_2 C7_2 H7B_2 109.5 . . ?
C2_2 C7_2 H7C_2 109.5 . . ?
H7A_2 C7_2 H7B_2 109.5 . . ?
H7A_2 C7_2 H7C_2 109.5 . . ?
H7B_2 C7_2 H7C_2 109.5 . . ?
C4_2 C8_2 H8A_2 109.5 . . ?
C4_2 C8_2 H8B_2 109.5 . . ?
C4_2 C8_2 H8C_2 109.5 . . ?
H8A_2 C8_2 H8B_2 109.5 . . ?
H8A_2 C8_2 H8C_2 109.5 . . ?
H8B_2 C8_2 H8C_2 109.5 . . ?
C6_2 C9_2 H9A_2 109.5 . . ?
C6_2 C9_2 H9B_2 109.5 . . ?
C6_2 C9_2 H9C_2 109.5 . . ?
H9A_2 C9_2 H9B_2 109.5 . . ?
H9A_2 C9_2 H9C_2 109.5 . . ?
H9B_2 C9_2 H9C_2 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1_1 B1_1 C1_2 C2_2 85.1(3) . . . . ?
Cl1_1 B1_1 C1_2 C6_2 -92.2(3) . . . . ?
Si1_1 N1_1 B1_1 Cl1_1 3.4(3) . . . . ?
Si1_1 N1_1 B1_1 C1_2 -176.45(18) . . . . ?
N1_1 B1_1 C1_2 C2_2 -95.1(3) . . . . ?
N1_1 B1_1 C1_2 C6_2 87.6(3) . . . . ?
B1_1 C1_2 C2_2 C3_2 -176.4(2) . . . . ?
B1_1 C1_2 C2_2 C7_2 5.0(3) . . . . ?
B1_1 C1_2 C6_2 C5_2 177.4(2) . . . . ?
B1_1 C1_2 C6_2 C9_2 -2.6(4) . . . . ?
C1_1 N1_1 B1_1 Cl1_1 -175.95(18) . . . . ?
C1_1 N1_1 B1_1 C1_2 4.2(4) . . . . ?
C2_1 Si1_1 N1_1 B1_1 177.5(2) . . . . ?
C2_1 Si1_1 N1_1 C1_1 -3.1(2) . . . . ?
C3_1 Si1_1 N1_1 B1_1 59.5(2) . . . . ?
C3_1 Si1_1 N1_1 C1_1 -121.15(18) . . . . ?
C4_1 Si1_1 N1_1 B1_1 -63.9(2) . . . . ?
C4_1 Si1_1 N1_1 C1_1 115.51(19) . . . . ?
C1_2 C2_2 C3_2 C4_2 -1.3(4) . . . . ?
C2_2 C1_2 C6_2 C5_2 0.0(4) . . . . ?
C2_2 C1_2 C6_2 C9_2 180.0(2) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.5(4) . . . . ?
C2_2 C3_2 C4_2 C8_2 -179.4(2) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.6(4) . . . . ?
C4_2 C5_2 C6_2 C1_2 -0.8(4) . . . . ?
C4_2 C5_2 C6_2 C9_2 179.2(2) . . . . ?
C6_2 C1_2 C2_2 C3_2 1.0(3) . . . . ?
C6_2 C1_2 C2_2 C7_2 -177.6(2) . . . . ?
C7_2 C2_2 C3_2 C4_2 177.3(2) . . . . ?
C8_2 C4_2 C5_2 C6_2 -179.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
