# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Madison02_a
_database_code_depnum_ccdc_archive 'CCDC 2373783'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2024-07-26 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Borane-N-benzyl-1-cyclohexylmethanamine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 B N'
_chemical_formula_weight         217.15

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'
N N 0.0061 0.0033 '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'

_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                   8.552(2)
_cell_length_b                   9.056(4)
_cell_length_c                   9.909(3)
_cell_angle_alpha                68.308(10)
_cell_angle_beta                 71.722(13)
_cell_angle_gamma                79.828(13)
_cell_volume                     675.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.4263
_cell_measurement_theta_max      32.6894

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D. (2015). J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            42471
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.298
_diffrn_reflns_theta_max         33.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5179
_reflns_number_gt                3780
_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       'Apex4 v2022.10-1 (Bruker, 2022)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1573 (Hübschle et al., 2011)
;
_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)+(0.0586P)²+0.1274P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5179
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
B1 B 0.22699(13) 0.41303(13) 0.98453(11) 0.0275(2) Uani 1 1 d . . . . .
H1B H 0.1213(9) 0.3304(8) 1.0374(6) 0.041 Uiso 1 1 calc R U . . .
H2B H 0.2278(10) 0.4747(4) 1.0660(6) 0.041 Uiso 1 1 calc R U . . .
H3B H 0.3494(9) 0.3404(8) 0.9601(2) 0.041 Uiso 1 1 calc R U . . .
C1 C 0.01105(11) 0.71469(12) 0.58693(10) 0.02770(18) Uani 1 1 d . . . . .
H1 H -0.051913 0.731067 0.678652 0.033 Uiso 1 1 calc R U . . .
C2 C -0.01381(13) 0.81949(13) 0.45067(11) 0.0317(2) Uani 1 1 d . . . . .
H2 H -0.092974 0.907592 0.449637 0.038 Uiso 1 1 calc R U . . .
C3 C 0.07655(13) 0.79603(13) 0.31601(11) 0.0335(2) Uani 1 1 d . . . . .
H3 H 0.059103 0.867623 0.223000 0.040 Uiso 1 1 calc R U . . .
C4 C 0.19199(13) 0.66803(14) 0.31791(11) 0.0347(2) Uani 1 1 d . . . . .
H4 H 0.253958 0.651337 0.226091 0.042 Uiso 1 1 calc R U . . .
C5 C 0.21741(12) 0.56372(12) 0.45420(11) 0.02988(19) Uani 1 1 d . . . . .
H5 H 0.297190 0.476165 0.454627 0.036 Uiso 1 1 calc R U . . .
C6 C 0.12773(10) 0.58569(11) 0.58995(9) 0.02340(16) Uani 1 1 d . . . . .
C7 C 0.15498(11) 0.46995(11) 0.73717(10) 0.02530(17) Uani 1 1 d . . . . .
H7A H 0.052527 0.414924 0.797931 0.030 Uiso 1 1 calc R U . . .
H7B H 0.243072 0.388312 0.715360 0.030 Uiso 1 1 calc R U . . .
C8 C 0.35072(11) 0.63788(11) 0.73871(10) 0.02487(17) Uani 1 1 d . . . . .
H8A H 0.333751 0.705405 0.639198 0.030 Uiso 1 1 calc R U . . .
H8B H 0.446857 0.561891 0.720773 0.030 Uiso 1 1 calc R U . . .
C9 C 0.39267(10) 0.74399(10) 0.80936(9) 0.02302(16) Uani 1 1 d . . . . .
H9 H 0.420440 0.675507 0.905387 0.028 Uiso 1 1 calc R U . . .
C10 C 0.25011(12) 0.86424(12) 0.84380(11) 0.03004(19) Uani 1 1 d . . . . .
H10A H 0.157869 0.806686 0.925234 0.036 Uiso 1 1 calc R U . . .
H10B H 0.210235 0.920379 0.752840 0.036 Uiso 1 1 calc R U . . .
C11 C 0.30060(14) 0.98665(13) 0.89222(12) 0.0358(2) Uani 1 1 d . . . . .
H11A H 0.206596 1.065509 0.907499 0.043 Uiso 1 1 calc R U . . .
H11B H 0.328576 0.932249 0.989434 0.043 Uiso 1 1 calc R U . . .
C12 C 0.44852(14) 1.07242(12) 0.77414(12) 0.0349(2) Uani 1 1 d . . . . .
H12A H 0.417839 1.134146 0.679235 0.042 Uiso 1 1 calc R U . . .
H12B H 0.480950 1.148009 0.809966 0.042 Uiso 1 1 calc R U . . .
C13 C 0.59351(13) 0.95410(13) 0.74403(13) 0.0347(2) Uani 1 1 d . . . . .
H13A H 0.631834 0.900865 0.836175 0.042 Uiso 1 1 calc R U . . .
H13B H 0.685776 1.011733 0.662720 0.042 Uiso 1 1 calc R U . . .
C14 C 0.54589(12) 0.82885(12) 0.69780(11) 0.02972(19) Uani 1 1 d . . . . .
H14A H 0.639869 0.748521 0.688588 0.036 Uiso 1 1 calc R U . . .
H14B H 0.525078 0.880720 0.597294 0.036 Uiso 1 1 calc R U . . .
N1 N 0.20203(9) 0.54537(9) 0.82904(8) 0.02192(14) Uani 1 1 d . . . . .
H1N H 0.1140(16) 0.6122(16) 0.8542(14) 0.033 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
B1 N1 1.6146(13) . ?
B1 H1B 1.142(8) . ?
B1 H2B 1.142(8) . ?
B1 H3B 1.142(8) . ?
C1 C2 1.3895(13) . ?
C1 C6 1.3937(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.3884(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3820(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3900(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3908(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.5092(13) . ?
C7 N1 1.4979(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.4926(12) . ?
C8 C9 1.5228(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5276(13) . ?
C9 C14 1.5325(13) . ?
C9 H9 1.0000 . ?
C10 C11 1.5290(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5229(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5197(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5253(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 H1N 0.910(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 B1 H1B 109.5 . . ?
N1 B1 H2B 109.5 . . ?
H1B B1 H2B 109.5 . . ?
N1 B1 H3B 109.5 . . ?
H1B B1 H3B 109.5 . . ?
H2B B1 H3B 109.5 . . ?
C2 C1 C6 120.44(9) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.29(10) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.69(9) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.98(9) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.95(10) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.64(8) . . ?
C5 C6 C7 120.30(9) . . ?
C1 C6 C7 121.06(8) . . ?
N1 C7 C6 114.18(8) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C9 115.57(7) . . ?
N1 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
N1 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 112.33(7) . . ?
C8 C9 C14 106.82(7) . . ?
C10 C9 C14 110.94(8) . . ?
C8 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C14 C9 H9 108.9 . . ?
C9 C10 C11 112.25(8) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 111.22(9) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 110.76(9) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.30(9) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C9 113.45(8) . . ?
C13 C14 H14A 108.9 . . ?
C9 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C9 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C8 N1 C7 110.64(7) . . ?
C8 N1 B1 112.47(7) . . ?
C7 N1 B1 110.62(7) . . ?
C8 N1 H1N 109.8(8) . . ?
C7 N1 H1N 105.9(8) . . ?
B1 N1 H1N 107.1(8) . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes'
