# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_liu107a
_database_code_depnum_ccdc_archive 'CCDC 2103581'
loop_
_audit_author_name
_audit_author_address
'Lev N. Zakharov'
;University of Oregon
United States of America
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXLTL
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H12 B N'
_chemical_formula_weight         84.96

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.60(4)
_cell_length_b                   6.32(2)
_cell_length_c                   9.48(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.06(3)
_cell_angle_gamma                90.00
_cell_volume                     631(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    30
_cell_measurement_theta_min      11.34
_cell_measurement_theta_max      18.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.894
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_T_max  0.9995
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5074
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1116
_reflns_number_gt                800
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0997P)²+0.1657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1116
_refine_ls_number_parameters     80
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1964
_refine_ls_wR_factor_gt          0.1778
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3886(2) 1.1065(3) 0.81466(19) 0.0407(6) Uani 1 1 d . . .
B1 B 0.3697(3) 1.2166(4) 0.6551(3) 0.0437(7) Uani 1 1 d . A .
C1 C 0.2762(2) 0.9599(4) 0.8242(2) 0.0534(8) Uani 0.50 1 d P A 1
H1A H 0.3011 0.8366 0.8853 0.064 Uiso 0.50 1 calc PR A 1
H1B H 0.2062 1.0356 0.8641 0.064 Uiso 0.50 1 calc PR A 1
C2 C 0.2344(3) 0.8875(5) 0.6701(3) 0.0381(11) Uani 0.743(8) 1 d P A 1
H2A H 0.3008 0.7876 0.6425 0.046 Uiso 0.743(8) 1 calc PR A 1
C3 C 0.2445(3) 1.0902(4) 0.5825(3) 0.0583(8) Uani 0.50 1 d P A 1
H3A H 0.1674 1.1782 0.5850 0.070 Uiso 0.50 1 calc PR A 1
H3B H 0.2543 1.0549 0.4825 0.070 Uiso 0.50 1 calc PR A 1
C4 C 0.1079(5) 0.7689(9) 0.6518(7) 0.0548(13) Uani 0.743(8) 1 d P A 1
H4A H 0.1133 0.6435 0.7130 0.082 Uiso 0.743(8) 1 calc PR A 1
H4B H 0.0891 0.7252 0.5526 0.082 Uiso 0.743(8) 1 calc PR A 1
H4C H 0.0402 0.8620 0.6781 0.082 Uiso 0.743(8) 1 calc PR A 1
C1A C 0.2762(2) 0.9599(4) 0.8242(2) 0.0534(8) Uani 0.50 1 d P A 2
H1AA H 0.3044 0.8104 0.8261 0.064 Uiso 0.50 1 calc PR A 2
H1AB H 0.2361 0.9890 0.9119 0.064 Uiso 0.50 1 calc PR A 2
C2A C 0.1903(10) 0.996(2) 0.7060(11) 0.054(4) Uiso 0.257(8) 1 d P A 2
H2AA H 0.1378 1.1150 0.7382 0.064 Uiso 0.257(8) 1 calc PR A 2
C3A C 0.2445(3) 1.0902(4) 0.5825(3) 0.0583(8) Uani 0.50 1 d P A 2
H3AA H 0.1836 1.1886 0.5302 0.070 Uiso 0.50 1 calc PR A 2
H3AB H 0.2684 0.9790 0.5167 0.070 Uiso 0.50 1 calc PR A 2
C4A C 0.0915(18) 0.812(3) 0.682(2) 0.073(7) Uiso 0.257(8) 1 d P A 2
H4AA H 0.0629 0.7709 0.7736 0.109 Uiso 0.257(8) 1 calc PR A 2
H4AB H 0.1312 0.6898 0.6409 0.109 Uiso 0.257(8) 1 calc PR A 2
H4AC H 0.0185 0.8590 0.6180 0.109 Uiso 0.257(8) 1 calc PR A 2
H1BA H 0.464(2) 1.182(3) 0.607(2) 0.045(6) Uiso 1 1 d . . .
H2BB H 0.358(2) 1.400(4) 0.669(3) 0.057(7) Uiso 1 1 d . . .
H2NB H 0.461(3) 1.026(5) 0.831(3) 0.062(8) Uiso 1 1 d . . .
H1NA H 0.397(2) 1.202(4) 0.884(3) 0.055(7) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0563(13) 0.0421(12) 0.0232(10) -0.0036(8) 0.0013(8) 0.0047(10)
B1 0.0598(18) 0.0405(15) 0.0296(13) 0.0054(11) -0.0007(12) -0.0015(13)
C1 0.0716(17) 0.0569(16) 0.0334(13) 0.0048(11) 0.0133(11) -0.0045(13)
C2 0.049(2) 0.0326(19) 0.0338(17) -0.0018(12) 0.0098(13) 0.0027(14)
C3 0.081(2) 0.0556(16) 0.0356(14) 0.0072(11) -0.0079(12) -0.0156(14)
C4 0.053(2) 0.051(3) 0.063(3) -0.008(2) 0.015(2) -0.0092(19)
C1A 0.0716(17) 0.0569(16) 0.0334(13) 0.0048(11) 0.0133(11) -0.0045(13)
C3A 0.081(2) 0.0556(16) 0.0356(14) 0.0072(11) -0.0079(12) -0.0156(14)

_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 1.519(5) . ?
N1 B1 1.658(6) . ?
N1 H2NB 0.92(3) . ?
N1 H1NA 0.89(3) . ?
B1 C3 1.637(5) . ?
B1 H1BA 1.16(2) . ?
B1 H2BB 1.18(2) . ?
C1 C2 1.550(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C4 1.530(7) . ?
C2 C3 1.536(6) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C2A C4A 1.57(2) . ?
C2A H2AA 1.0000 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 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
C1 N1 B1 106.9(2) . . ?
C1 N1 H2NB 107.4(18) . . ?
B1 N1 H2NB 113.9(17) . . ?
C1 N1 H1NA 112.7(17) . . ?
B1 N1 H1NA 112.5(17) . . ?
H2NB N1 H1NA 103(2) . . ?
N1 B1 C3 101.2(2) . . ?
N1 B1 H1BA 104.7(11) . . ?
C3 B1 H1BA 115.7(11) . . ?
N1 B1 H2BB 108.2(12) . . ?
C3 B1 H2BB 116.1(12) . . ?
H1BA B1 H2BB 109.8(17) . . ?
C2 C1 N1 105.8(2) . . ?
C2 C1 H1A 110.6 . . ?
N1 C1 H1A 110.6 . . ?
C2 C1 H1B 110.6 . . ?
N1 C1 H1B 110.6 . . ?
H1A C1 H1B 108.7 . . ?
C1 C2 C4 114.3(3) . . ?
C1 C2 C3 103.6(3) . . ?
C4 C2 C3 117.2(3) . . ?
C1 C2 H2A 107.1 . . ?
C4 C2 H2A 107.1 . . ?
C3 C2 H2A 107.1 . . ?
C2 C3 B1 106.2(3) . . ?
C2 C3 H3A 110.5 . . ?
B1 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
B1 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C4A C2A H2AA 102.5 . . ?
C2A C4A H4AA 109.5 . . ?
C2A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
C2A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 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
C1 N1 B1 C3 -5.5(2) . . . . ?
B1 N1 C1 C2 28.4(3) . . . . ?
N1 C1 C2 C4 -169.9(3) . . . . ?
N1 C1 C2 C3 -41.2(3) . . . . ?
C1 C2 C3 B1 37.2(3) . . . . ?
C4 C2 C3 B1 164.0(3) . . . . ?
N1 B1 C3 C2 -19.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.184
_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_liu167
_database_code_depnum_ccdc_archive 'CCDC 2103582'
loop_
_audit_author_name
_audit_author_address
'Lev N. Zakharov'
;University of Oregon
United States of America
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXLTL
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H12 B N'
_chemical_formula_weight         84.96

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_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                   7.078(7)
_cell_length_b                   9.187(9)
_cell_length_c                   18.233(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1186(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    702
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      19.23

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.952
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7701
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_av_sigmaI/netI    0.1059
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1046
_reflns_number_gt                603
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0812P)²+1.1150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1046
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.2279
_refine_ls_wR_factor_gt          0.1888
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0938(5) 0.2726(4) 0.31226(19) 0.0337(10) Uani 1 1 d . . .
B1 B 0.2668(8) 0.1606(5) 0.3302(2) 0.0372(13) Uani 1 1 d . . .
C1 C -0.0578(6) 0.2522(4) 0.3688(2) 0.0371(11) Uani 1 1 d . . .
C2 C 0.0481(7) 0.2010(5) 0.4359(2) 0.0394(12) Uani 1 1 d . . .
C3 C 0.1999(7) 0.0947(5) 0.4086(2) 0.0417(13) Uani 1 1 d . . .
C4 C -0.1835(7) 0.3842(5) 0.3778(3) 0.0423(12) Uani 1 1 d . . .
H1 H -0.132(5) 0.160(4) 0.3477(19) 0.034(10) Uiso 1 1 d . . .
H1BA H 0.392(5) 0.226(4) 0.333(2) 0.041(11) Uiso 1 1 d . . .
H1BB H 0.267(5) 0.078(4) 0.2806(18) 0.034(9) Uiso 1 1 d . . .
H1NA H 0.131(6) 0.348(5) 0.314(2) 0.037(13) Uiso 1 1 d . . .
H1NB H 0.046(4) 0.256(3) 0.267(2) 0.019(10) Uiso 1 1 d . . .
H2A H -0.039(5) 0.169(3) 0.4731(19) 0.024(9) Uiso 1 1 d . . .
H2B H 0.104(6) 0.287(5) 0.463(3) 0.076(16) Uiso 1 1 d . . .
H3A H 0.148(6) 0.004(5) 0.403(2) 0.061(14) Uiso 1 1 d . . .
H3B H 0.295(7) 0.090(5) 0.443(3) 0.060(14) Uiso 1 1 d . . .
H4A H -0.099(7) 0.467(6) 0.398(3) 0.079(16) Uiso 1 1 d . . .
H4B H -0.294(5) 0.372(4) 0.415(2) 0.044(11) Uiso 1 1 d . . .
H4C H -0.234(6) 0.417(4) 0.328(2) 0.053(12) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.055(2) 0.0152(18) 0.031(2) 0.0021(13) 0.0027(18) -0.0020(16)
B1 0.050(3) 0.024(2) 0.037(3) 0.0010(19) 0.002(2) 0.005(2)
C1 0.050(3) 0.023(2) 0.038(2) 0.0044(16) 0.006(2) 0.004(2)
C2 0.051(3) 0.034(2) 0.033(2) 0.0060(18) 0.008(2) 0.007(2)
C3 0.061(3) 0.030(3) 0.034(2) 0.0040(18) -0.001(2) 0.008(2)
C4 0.044(3) 0.041(3) 0.042(3) 0.004(2) -0.001(2) 0.008(2)

_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 1.500(5) . ?
N1 B1 1.633(6) . ?
N1 H1NA 0.74(4) . ?
N1 H1NB 0.90(4) . ?
B1 C3 1.624(6) . ?
B1 H1BA 1.07(4) . ?
B1 H1BB 1.18(3) . ?
C1 C2 1.509(6) . ?
C1 C4 1.513(6) . ?
C1 H1 1.07(4) . ?
C2 C3 1.534(6) . ?
C2 H2A 0.96(3) . ?
C2 H2B 1.02(5) . ?
C3 H3A 0.92(5) . ?
C3 H3B 0.92(5) . ?
C4 H4A 1.03(5) . ?
C4 H4B 1.05(4) . ?
C4 H4C 1.03(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
C1 N1 B1 108.7(3) . . ?
C1 N1 H1NA 109(3) . . ?
B1 N1 H1NA 108(3) . . ?
C1 N1 H1NB 110(2) . . ?
B1 N1 H1NB 111(2) . . ?
H1NA N1 H1NB 110(4) . . ?
C3 B1 N1 101.1(3) . . ?
C3 B1 H1BA 114(2) . . ?
N1 B1 H1BA 106.3(19) . . ?
C3 B1 H1BB 115.8(16) . . ?
N1 B1 H1BB 104.7(16) . . ?
H1BA B1 H1BB 113(3) . . ?
N1 C1 C2 103.9(3) . . ?
N1 C1 C4 113.2(3) . . ?
C2 C1 C4 117.0(4) . . ?
N1 C1 H1 101.8(19) . . ?
C2 C1 H1 106.8(19) . . ?
C4 C1 H1 112.6(19) . . ?
C1 C2 C3 106.5(3) . . ?
C1 C2 H2A 110(2) . . ?
C3 C2 H2A 118.9(19) . . ?
C1 C2 H2B 110(3) . . ?
C3 C2 H2B 112(3) . . ?
H2A C2 H2B 98(3) . . ?
C2 C3 B1 104.6(3) . . ?
C2 C3 H3A 109(3) . . ?
B1 C3 H3A 111(3) . . ?
C2 C3 H3B 109(3) . . ?
B1 C3 H3B 114(3) . . ?
H3A C3 H3B 109(4) . . ?
C1 C4 H4A 107(3) . . ?
C1 C4 H4B 115(2) . . ?
H4A C4 H4B 107(3) . . ?
C1 C4 H4C 110(2) . . ?
H4A C4 H4C 107(3) . . ?
H4B C4 H4C 111(3) . . ?

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
C1 N1 B1 C3 -7.1(4) . . . . ?
B1 N1 C1 C2 28.5(4) . . . . ?
B1 N1 C1 C4 156.5(3) . . . . ?
N1 C1 C2 C3 -40.1(4) . . . . ?
C4 C1 C2 C3 -165.7(4) . . . . ?
C1 C2 C3 B1 35.4(5) . . . . ?
N1 B1 C3 C2 -16.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_C6H16BN
_database_code_depnum_ccdc_archive 'CCDC 2103584'
loop_
_audit_author_name
_audit_author_address
'Bo Li'
;Boston College
United States of America
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT049_C6H16BN             
;
PROBLEM: Calculated Density less than 1.0 gcm-3 .........     0.9562 Check 
RESPONSE: The density is comfirmed as well as the space group.
;
_vrf_PLAT415_C6H16BN             
;
PROBLEM: Short Inter D-H..H-X       H1N    ..  H2      ..       1.98 Ang.  
RESPONSE: The short Inter H-H contacts are due to crystal packing.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H16 B N'
_chemical_formula_sum            'C6 H16 B N'
_chemical_formula_weight         113.01

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.5116(14)
_cell_length_b                   12.6484(18)
_cell_length_c                   6.5253(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     785.04(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8070
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.41

_exptl_crystal_description       cube
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    0.956
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.054
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14886
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.679
_diffrn_reflns_theta_max         28.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1988
_reflns_number_gt                1925
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0587P)²+0.0622P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1988
_refine_ls_number_parameters     79
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
N1 N 0.44802(10) 0.24437(8) 0.42210(16) 0.0167(2) Uani 1 1 d . . . . .
H1N H 0.5255(18) 0.2460(12) 0.490(3) 0.020 Uiso 1 1 d . U . . .
B1 B 0.32334(14) 0.21257(11) 0.5816(2) 0.0212(3) Uani 1 1 d . . . . .
H2 H 0.2249(17) 0.2100(13) 0.476(3) 0.025 Uiso 1 1 d . U . . .
C1 C 0.46529(15) 0.16766(11) 0.2513(2) 0.0267(3) Uani 1 1 d . . . . .
H1A H 0.4761 0.0962 0.3073 0.040 Uiso 1 1 calc R U . . .
H1B H 0.3822 0.1701 0.1626 0.040 Uiso 1 1 calc R U . . .
H1C H 0.5490 0.1861 0.1713 0.040 Uiso 1 1 calc R U . . .
C2 C 0.43147(13) 0.35377(9) 0.3373(2) 0.0200(3) Uani 1 1 d . . . . .
H2A H 0.3435 0.3577 0.2564 0.024 Uiso 1 1 calc R U . . .
H2B H 0.5110 0.3695 0.2443 0.024 Uiso 1 1 calc R U . . .
C3 C 0.42707(13) 0.43569(9) 0.5073(2) 0.0211(3) Uani 1 1 d . . . . .
H3A H 0.4189 0.5070 0.4458 0.025 Uiso 1 1 calc R U . . .
H3B H 0.5164 0.4330 0.5850 0.025 Uiso 1 1 calc R U . . .
C4 C 0.30466(13) 0.41828(10) 0.6549(2) 0.0257(3) Uani 1 1 d . . . . .
H4A H 0.2146 0.4262 0.5806 0.031 Uiso 1 1 calc R U . . .
H4B H 0.3077 0.4721 0.7651 0.031 Uiso 1 1 calc R U . . .
C5 C 0.31343(14) 0.30746(11) 0.7490(2) 0.0267(3) Uani 1 1 d . . . . .
H5A H 0.2294 0.2958 0.8357 0.032 Uiso 1 1 calc R U . . .
H5B H 0.3971 0.3041 0.8391 0.032 Uiso 1 1 calc R U . . .
C6 C 0.35805(15) 0.09886(11) 0.6827(2) 0.0294(3) Uani 1 1 d . . . . .
H6A H 0.3627 0.0451 0.5748 0.044 Uiso 1 1 calc R U . . .
H6B H 0.4486 0.1024 0.7541 0.044 Uiso 1 1 calc R U . . .
H6C H 0.2839 0.0802 0.7805 0.044 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0151(4) 0.0159(5) 0.0190(4) 0.0001(4) -0.0017(4) 0.0004(3)
B1 0.0165(5) 0.0211(6) 0.0261(6) 0.0053(6) 0.0026(5) -0.0004(5)
C1 0.0330(7) 0.0206(6) 0.0265(6) -0.0057(5) 0.0027(5) -0.0002(5)
C2 0.0246(5) 0.0168(5) 0.0186(5) 0.0026(5) 0.0000(5) -0.0002(4)
C3 0.0247(6) 0.0161(5) 0.0224(6) -0.0004(5) -0.0012(5) 0.0008(4)
C4 0.0272(6) 0.0223(6) 0.0276(6) -0.0011(5) 0.0033(5) 0.0061(5)
C5 0.0296(7) 0.0265(6) 0.0239(6) 0.0039(5) 0.0083(5) 0.0046(5)
C6 0.0302(6) 0.0229(6) 0.0350(7) 0.0101(6) 0.0008(6) -0.0027(5)

_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 1.4870(17) . ?
N1 C2 1.4986(14) . ?
N1 B1 1.6283(17) . ?
N1 H1N 0.859(17) . ?
B1 C6 1.6163(19) . ?
B1 C5 1.626(2) . ?
B1 H2 1.163(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5189(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5271(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5326(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C1 N1 C2 109.70(10) . . ?
C1 N1 B1 113.48(10) . . ?
C2 N1 B1 112.81(9) . . ?
C1 N1 H1N 107.8(11) . . ?
C2 N1 H1N 105.0(10) . . ?
B1 N1 H1N 107.6(11) . . ?
C6 B1 C5 113.23(12) . . ?
C6 B1 N1 109.39(10) . . ?
C5 B1 N1 106.82(10) . . ?
C6 B1 H2 112.4(8) . . ?
C5 B1 H2 111.8(8) . . ?
N1 B1 H2 102.5(9) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 111.27(10) . . ?
N1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 112.55(10) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 110.06(10) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 B1 114.15(11) . . ?
C4 C5 H5A 108.7 . . ?
B1 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
B1 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
B1 C6 H6A 109.5 . . ?
B1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
B1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C1 N1 B1 C6 60.24(14) . . . . ?
C2 N1 B1 C6 -174.20(11) . . . . ?
C1 N1 B1 C5 -176.85(10) . . . . ?
C2 N1 B1 C5 -51.30(13) . . . . ?
C1 N1 C2 C3 -174.75(10) . . . . ?
B1 N1 C2 C3 57.68(12) . . . . ?
N1 C2 C3 C4 -60.39(12) . . . . ?
C2 C3 C4 C5 57.64(14) . . . . ?
C3 C4 C5 B1 -54.15(14) . . . . ?
C6 B1 C5 C4 170.53(11) . . . . ?
N1 B1 C5 C4 50.06(13) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.033

_shelxl_version_number           2014-3

_shelx_res_file                  
;
TITL sada in Pna2(1)
CELL 0.71073   9.51160  12.64840   6.52530  90.0000  90.0000  90.0000
ZERR    4.00   0.00140   0.00180   0.00090   0.0000   0.0000   0.0000
LATT -1
SYMM -X, -Y, 0.5+Z
SYMM 0.5+X, 0.5-Y, Z
SYMM 0.5-X, 0.5+Y, 0.5+Z
SFAC C  H  B  N
UNIT 24  64  4  4

L.S. 10
BOND $H
FMAP 2
PLAN -20
TEMP -173
SIZE 0.45 0.38 0.32
CONF
HTAB
ACTA
WGHT    0.058700    0.062200
FVAR       0.36144
N1    4    0.448023    0.244372    0.422099    11.00000    0.01514    0.01594 =
         0.01897    0.00006   -0.00166    0.00041
H1N   2    0.525459    0.245973    0.489700    11.00000   -1.20000
B1    3    0.323345    0.212566    0.581589    11.00000    0.01651    0.02112 =
         0.02607    0.00532    0.00256   -0.00039
H2    2    0.224851    0.210029    0.476206    11.00000   -1.20000
C1    1    0.465287    0.167660    0.251256    11.00000    0.03297    0.02063 =
         0.02650   -0.00566    0.00270   -0.00016
AFIX  33
H1A   2    0.476076    0.096235    0.307296    11.00000   -1.50000
H1B   2    0.382190    0.170061    0.162586    11.00000   -1.50000
H1C   2    0.548973    0.186126    0.171293    11.00000   -1.50000
AFIX   0
C2    1    0.431474    0.353770    0.337260    11.00000    0.02457    0.01683 =
         0.01860    0.00258   -0.00002   -0.00019
AFIX  23
H2A   2    0.343542    0.357692    0.256443    11.00000   -1.20000
H2B   2    0.511010    0.369506    0.244272    11.00000   -1.20000
AFIX   0
C3    1    0.427074    0.435687    0.507343    11.00000    0.02470    0.01612 =
         0.02237   -0.00044   -0.00119    0.00078
AFIX  23
H3A   2    0.418867    0.506963    0.445803    11.00000   -1.20000
H3B   2    0.516430    0.433020    0.584972    11.00000   -1.20000
AFIX   0
C4    1    0.304656    0.418284    0.654949    11.00000    0.02716    0.02234 =
         0.02760   -0.00112    0.00332    0.00605
AFIX  23
H4A   2    0.214553    0.426219    0.580573    11.00000   -1.20000
H4B   2    0.307723    0.472077    0.765066    11.00000   -1.20000
AFIX   0
C5    1    0.313434    0.307461    0.749031    11.00000    0.02964    0.02653 =
         0.02391    0.00386    0.00833    0.00464
AFIX  23
H5A   2    0.229418    0.295819    0.835698    11.00000   -1.20000
H5B   2    0.397053    0.304105    0.839137    11.00000   -1.20000
AFIX   0
C6    1    0.358050    0.098861    0.682683    11.00000    0.03025    0.02291 =
         0.03503    0.01008    0.00076   -0.00271
AFIX  33
H6A   2    0.362677    0.045095    0.574755    11.00000   -1.50000
H6B   2    0.448584    0.102352    0.754058    11.00000   -1.50000
H6C   2    0.283931    0.080196    0.780529    11.00000   -1.50000

AFIX   0
HKLF 4

REM  sada in Pna2(1)
REM R1 =  0.0325 for    1925 Fo > 4sig(Fo)  and  0.0338 for all    1988 data
REM     79 parameters refined using      1 restraints

END

WGHT      0.0586      0.0622

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.301,  deepest hole -0.126,  1-sigma level  0.033
Q1    1   0.3180  0.2609  0.6654  11.00000  0.05    0.30
Q2    1   0.4282  0.4000  0.4228  11.00000  0.05    0.28
Q3    1   0.3084  0.3622  0.7101  11.00000  0.05    0.25
Q4    1   0.4423  0.2982  0.3865  11.00000  0.05    0.22
Q5    1   0.3427  0.1529  0.6395  11.00000  0.05    0.20
Q6    1   0.4504  0.2037  0.3491  11.00000  0.05    0.19
Q7    1   0.3654  0.4230  0.5797  11.00000  0.05    0.18
Q8    1   0.3915  0.2255  0.4880  11.00000  0.05    0.16
Q9    1   0.3768  0.1547  0.2241  11.00000  0.05    0.14
Q10   1   0.3318  0.0421  0.6325  11.00000  0.05    0.12
Q11   1   0.5099  0.1176  0.3238  11.00000  0.05    0.11
Q12   1   0.3374  0.1037  0.7890  11.00000  0.05    0.11
Q13   1   0.1991  0.1963  0.4181  11.00000  0.05    0.10
Q14   1   0.5135  0.2011  0.1370  11.00000  0.05    0.10
Q15   1   0.2481  0.1774  0.5057  11.00000  0.05    0.09
Q16   1   0.2774  0.3019  0.8992  11.00000  0.05    0.09
Q17   1   0.4676  0.3560  0.2568  11.00000  0.05    0.09
Q18   1   0.3134  0.2990  0.8162  11.00000  0.05    0.09
Q19   1   0.1588  0.2691  0.8455  11.00000  0.05    0.08
Q20   1   0.2782  0.4762  0.7008  11.00000  0.05    0.08
;
_shelx_res_checksum              21426
####################################################################### 
# 
# 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_liu104a
_database_code_depnum_ccdc_archive 'CCDC 2103583'
loop_
_audit_author_name
_audit_author_address
'Lev N. Zakharov'
;University of Oregon
United States of America
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXLTL
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H10 B N'
_chemical_formula_sum            'C3 H10 B N'
_chemical_formula_weight         70.93

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   8.519(3)
_cell_length_b                   6.850(2)
_cell_length_c                   8.309(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     484.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1133
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      24.79

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.972
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             160
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4991
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         26.99
_reflns_number_total             1065
_reflns_number_gt                901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.0785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1065
_refine_ls_number_parameters     66
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.081
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.13347(17) 0.4024(2) 0.72507(14) 0.0311(4) Uani 1 1 d . . .
B1 B 0.0167(2) 0.4442(3) 0.8751(3) 0.0341(5) Uani 1 1 d . A .
C1 C 0.1275(3) 0.1907(3) 0.6882(3) 0.0501(6) Uani 0.693(4) 1 d PD A 1
H1A H 0.0726 0.1692 0.5847 0.060 Uiso 0.693(4) 1 calc PR A 1
H1B H 0.2354 0.1380 0.6785 0.060 Uiso 0.693(4) 1 calc PR A 1
C2 C 0.0439(4) 0.0911(4) 0.8183(4) 0.0454(8) Uani 0.693(4) 1 d PD A 1
H2A H 0.1180 0.0509 0.9039 0.055 Uiso 0.693(4) 1 calc PR A 1
H2B H -0.0103 -0.0265 0.7769 0.055 Uiso 0.693(4) 1 calc PR A 1
C3 C -0.0769(3) 0.2400(3) 0.8847(4) 0.0564(7) Uani 0.693(4) 1 d PD A 1
H3A H -0.1064 0.2086 0.9970 0.068 Uiso 0.693(4) 1 calc PR A 1
H3B H -0.1728 0.2432 0.8174 0.068 Uiso 0.693(4) 1 calc PR A 1
C1A C 0.1275(3) 0.1907(3) 0.6882(3) 0.0501(6) Uani 0.307(4) 1 d PD A 2
H1AA H 0.1328 0.1672 0.5707 0.060 Uiso 0.307(4) 1 calc PR A 2
H1AB H 0.2145 0.1199 0.7414 0.060 Uiso 0.307(4) 1 calc PR A 2
C2A C -0.0284(9) 0.1300(10) 0.7552(9) 0.0454(8) Uani 0.307(4) 1 d PD A 2
H2AA H -0.1083 0.1396 0.6691 0.055 Uiso 0.307(4) 1 calc PR A 2
H2AB H -0.0221 -0.0085 0.7886 0.055 Uiso 0.307(4) 1 calc PR A 2
C3A C -0.0769(3) 0.2400(3) 0.8847(4) 0.0564(7) Uani 0.307(4) 1 d PD A 2
H3AA H -0.0526 0.1719 0.9867 0.068 Uiso 0.307(4) 1 calc PR A 2
H3AB H -0.1915 0.2629 0.8794 0.068 Uiso 0.307(4) 1 calc PR A 2
H1 H 0.230(2) 0.436(2) 0.752(2) 0.042(6) Uiso 1 1 d . . .
H2 H 0.100(3) 0.464(3) 0.645(3) 0.042(6) Uiso 1 1 d . . .
H3 H -0.054(2) 0.586(3) 0.848(3) 0.033(5) Uiso 1 1 d . . .
H4 H 0.086(3) 0.472(3) 0.985(2) 0.037(5) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0258(7) 0.0402(9) 0.0271(8) 0.0006(7) 0.0013(7) -0.0023(6)
B1 0.0275(9) 0.0448(12) 0.0299(9) 0.0009(9) 0.0034(9) 0.0037(8)
C1 0.0539(12) 0.0395(11) 0.0568(14) -0.0074(9) 0.0104(11) 0.0013(10)
C2 0.0466(19) 0.0354(14) 0.0543(19) 0.0033(12) -0.0031(13) 0.0011(13)
C3 0.0430(12) 0.0450(12) 0.0812(18) 0.0167(12) 0.0207(13) 0.0012(10)
C1A 0.0539(12) 0.0395(11) 0.0568(14) -0.0074(9) 0.0104(11) 0.0013(10)
C2A 0.0466(19) 0.0354(14) 0.0543(19) 0.0033(12) -0.0031(13) 0.0011(13)
C3A 0.0430(12) 0.0450(12) 0.0812(18) 0.0167(12) 0.0207(13) 0.0012(10)

_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 1.483(3) . ?
N1 B1 1.620(2) . ?
N1 H1 0.88(2) . ?
N1 H2 0.84(3) . ?
B1 C3 1.612(3) . ?
B1 H3 1.166(19) . ?
B1 H4 1.10(2) . ?
C1 C2 1.464(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.550(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?

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
C1 N1 B1 108.14(15) . . ?
C1 N1 H1 109.7(11) . . ?
B1 N1 H1 109.2(13) . . ?
C1 N1 H2 108.4(16) . . ?
B1 N1 H2 108.6(16) . . ?
H1 N1 H2 113(2) . . ?
C3 B1 N1 100.84(16) . . ?
C3 B1 H3 118.6(10) . . ?
N1 B1 H3 108.5(11) . . ?
C3 B1 H4 112.0(10) . . ?
N1 B1 H4 109.8(11) . . ?
H3 B1 H4 106.8(15) . . ?
C2 C1 N1 108.6(2) . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 . . ?
N1 C1 H1B 110.0 . . ?
H1A C1 H1B 108.3 . . ?
C1 C2 C3 106.2(2) . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C2 C3 B1 103.01(19) . . ?
C2 C3 H3A 111.2 . . ?
B1 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
B1 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
H2AA C2A H2AB 107.7 . . ?

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
C1 N1 B1 C3 -11.80(19) . . . . ?
B1 N1 C1 C2 -10.9(3) . . . . ?
N1 C1 C2 C3 30.5(3) . . . . ?
C1 C2 C3 B1 -37.2(3) . . . . ?
N1 B1 C3 C2 28.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.040
