# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_hl20-sr
_database_code_depnum_ccdc_archive 'CCDC 1847798'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 B N'
_chemical_formula_weight         395.37

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.4716(3)
_cell_length_b                   27.7566(10)
_cell_length_c                   11.7695(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.2570(10)
_cell_angle_gamma                90
_cell_volume                     2723.29(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4934
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.91

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.964
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.054
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40531
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         27.359
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6147
_reflns_number_gt                3966
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0900P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6147
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1921
_refine_ls_wR_factor_gt          0.1702
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_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 0.3657(3) 0.65872(8) 0.5777(2) 0.0339(5) Uani 1 1 d . . . . .
N1 N 0.43960(19) 0.68068(6) 0.70665(14) 0.0364(4) Uani 1 1 d . . . . .
C1 C 0.2510(2) 0.70484(7) 0.53625(18) 0.0368(5) Uani 1 1 d . . . . .
C2 C 0.1555(2) 0.71790(8) 0.4319(2) 0.0441(5) Uani 1 1 d . . . . .
H2 H 0.1384 0.6956 0.3697 0.053 Uiso 1 1 calc R U . . .
C3 C 0.0850(3) 0.76308(8) 0.4178(2) 0.0524(6) Uani 1 1 d . . . . .
H3 H 0.0191 0.7710 0.3462 0.063 Uiso 1 1 calc R U . . .
C4 C 0.1083(3) 0.79691(8) 0.5054(3) 0.0596(7) Uani 1 1 d . . . . .
H4 H 0.0565 0.8273 0.4944 0.072 Uiso 1 1 calc R U . . .
C5 C 0.2061(3) 0.78642(8) 0.6080(2) 0.0541(6) Uani 1 1 d . . . . .
H5 H 0.2263 0.8097 0.6679 0.065 Uiso 1 1 calc R U . . .
C6 C 0.2759(3) 0.74055(7) 0.62264(19) 0.0418(5) Uani 1 1 d . . . . .
C7 C 0.3811(3) 0.72263(7) 0.72197(19) 0.0424(5) Uani 1 1 d . . . . .
H7 H 0.4056 0.7399 0.7926 0.051 Uiso 1 1 calc R U . . .
C8 C 0.5328(3) 0.65376(8) 0.80577(18) 0.0436(5) Uani 1 1 d . . . . .
H8 H 0.5839 0.6256 0.7737 0.052 Uiso 1 1 calc R U . . .
C9 C 0.6652(4) 0.68341(12) 0.8754(2) 0.0852(10) Uani 1 1 d . . . . .
H9A H 0.7234 0.7006 0.8230 0.128 Uiso 1 1 calc R U . . .
H9B H 0.7393 0.6621 0.9256 0.128 Uiso 1 1 calc R U . . .
H9C H 0.6187 0.7067 0.9227 0.128 Uiso 1 1 calc R U . . .
C10 C 0.4229(3) 0.63434(11) 0.8829(2) 0.0745(8) Uani 1 1 d . . . . .
H10A H 0.3379 0.6151 0.8368 0.112 Uiso 1 1 calc R U . . .
H10B H 0.3749 0.6612 0.9187 0.112 Uiso 1 1 calc R U . . .
H10C H 0.4846 0.6141 0.9432 0.112 Uiso 1 1 calc R U . . .
C11 C 0.3016(2) 0.60528(7) 0.60660(17) 0.0344(4) Uani 1 1 d . . . . .
C12 C 0.1445(2) 0.59722(7) 0.62709(18) 0.0392(5) Uani 1 1 d . . . . .
C13 C 0.0910(3) 0.55141(8) 0.6465(2) 0.0477(5) Uani 1 1 d . . . . .
H13 H -0.0164 0.5473 0.6579 0.057 Uiso 1 1 calc R U . . .
C14 C 0.1892(3) 0.51114(8) 0.6499(2) 0.0488(6) Uani 1 1 d . . . . .
C15 C 0.3458(3) 0.51902(7) 0.63701(18) 0.0451(5) Uani 1 1 d . . . . .
H15 H 0.4173 0.4924 0.6434 0.054 Uiso 1 1 calc R U . . .
C16 C 0.4035(2) 0.56453(7) 0.61493(17) 0.0389(5) Uani 1 1 d . . . . .
C17 C 0.0269(3) 0.63809(8) 0.6312(2) 0.0560(6) Uani 1 1 d . . . . .
H17A H -0.0051 0.6517 0.5537 0.084 Uiso 1 1 calc R U . . .
H17B H 0.0779 0.6632 0.6840 0.084 Uiso 1 1 calc R U . . .
H17C H -0.0681 0.6258 0.6587 0.084 Uiso 1 1 calc R U . . .
C18 C 0.1277(4) 0.46127(8) 0.6677(3) 0.0727(8) Uani 1 1 d . . . . .
H18A H 0.0103 0.4611 0.6483 0.109 Uiso 1 1 calc R U . . .
H18B H 0.1614 0.4518 0.7487 0.109 Uiso 1 1 calc R U . . .
H18C H 0.1715 0.4384 0.6179 0.109 Uiso 1 1 calc R U . . .
C19 C 0.5777(3) 0.56587(8) 0.6003(2) 0.0475(5) Uani 1 1 d . . . . .
H19A H 0.5842 0.5612 0.5187 0.071 Uiso 1 1 calc R U . . .
H19B H 0.6372 0.5402 0.6464 0.071 Uiso 1 1 calc R U . . .
H19C H 0.6244 0.5972 0.6261 0.071 Uiso 1 1 calc R U . . .
C20 C 0.4819(2) 0.65856(6) 0.47820(16) 0.0327(4) Uani 1 1 d . . . . .
C21 C 0.4271(2) 0.63308(7) 0.37413(17) 0.0394(5) Uani 1 1 d . . . . .
C22 C 0.5165(3) 0.63319(8) 0.28533(18) 0.0452(5) Uani 1 1 d . . . . .
H22 H 0.4769 0.6156 0.2169 0.054 Uiso 1 1 calc R U . . .
C23 C 0.6598(3) 0.65767(7) 0.29229(18) 0.0424(5) Uani 1 1 d . . . . .
C24 C 0.7095(2) 0.68414(7) 0.39103(18) 0.0401(5) Uani 1 1 d . . . . .
H24 H 0.8055 0.7024 0.3973 0.048 Uiso 1 1 calc R U . . .
C25 C 0.6247(2) 0.68535(7) 0.48224(17) 0.0346(4) Uani 1 1 d . . . . .
C26 C 0.2740(3) 0.60374(8) 0.3519(2) 0.0508(6) Uani 1 1 d . . . . .
H26A H 0.2327 0.6026 0.2687 0.076 Uiso 1 1 calc R U . . .
H26B H 0.1940 0.6187 0.3913 0.076 Uiso 1 1 calc R U . . .
H26C H 0.2963 0.5709 0.3812 0.076 Uiso 1 1 calc R U . . .
C27 C 0.7581(3) 0.65570(9) 0.1975(2) 0.0599(7) Uani 1 1 d . . . . .
H27A H 0.7066 0.6340 0.1363 0.090 Uiso 1 1 calc R U . . .
H27B H 0.8659 0.6438 0.2290 0.090 Uiso 1 1 calc R U . . .
H27C H 0.7659 0.6881 0.1657 0.090 Uiso 1 1 calc R U . . .
C28 C 0.6954(3) 0.71627(8) 0.58380(19) 0.0446(5) Uani 1 1 d . . . . .
H28A H 0.7934 0.7317 0.5684 0.067 Uiso 1 1 calc R U . . .
H28B H 0.7211 0.6962 0.6531 0.067 Uiso 1 1 calc R U . . .
H28C H 0.6176 0.7410 0.5960 0.067 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
B1 C1 1.629(3) . ?
B1 C11 1.636(3) . ?
B1 N1 1.651(3) . ?
B1 C20 1.658(3) . ?
N1 C7 1.291(2) . ?
N1 C8 1.488(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.382(4) . ?
C4 C5 1.369(4) . ?
C5 C6 1.401(3) . ?
C6 C7 1.427(3) . ?
C8 C9 1.510(3) . ?
C8 C10 1.511(3) . ?
C11 C12 1.412(3) . ?
C11 C16 1.416(3) . ?
C12 C13 1.382(3) . ?
C12 C17 1.517(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.379(3) . ?
C14 C18 1.507(3) . ?
C15 C16 1.395(3) . ?
C16 C19 1.516(3) . ?
C20 C25 1.414(3) . ?
C20 C21 1.419(3) . ?
C21 C22 1.396(3) . ?
C21 C26 1.514(3) . ?
C22 C23 1.381(3) . ?
C23 C24 1.376(3) . ?
C23 C27 1.507(3) . ?
C24 C25 1.394(3) . ?
C25 C28 1.506(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
C1 B1 C11 124.92(17) . . ?
C1 B1 N1 95.37(14) . . ?
C11 B1 N1 103.25(15) . . ?
C1 B1 C20 100.84(15) . . ?
C11 B1 C20 113.88(15) . . ?
N1 B1 C20 118.33(16) . . ?
C7 N1 C8 120.45(17) . . ?
C7 N1 B1 111.66(17) . . ?
C8 N1 B1 126.61(15) . . ?
C2 C1 C6 116.25(19) . . ?
C2 C1 B1 133.68(19) . . ?
C6 C1 B1 109.39(18) . . ?
C3 C2 C1 120.8(2) . . ?
C4 C3 C2 121.6(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 118.5(2) . . ?
C5 C6 C1 123.0(2) . . ?
C5 C6 C7 127.3(2) . . ?
C1 C6 C7 109.73(17) . . ?
N1 C7 C6 113.53(18) . . ?
N1 C8 C9 113.00(19) . . ?
N1 C8 C10 110.64(19) . . ?
C9 C8 C10 110.3(2) . . ?
C12 C11 C16 116.30(17) . . ?
C12 C11 B1 122.48(17) . . ?
C16 C11 B1 121.21(17) . . ?
C13 C12 C11 121.40(19) . . ?
C13 C12 C17 116.47(19) . . ?
C11 C12 C17 122.12(17) . . ?
C12 C13 C14 122.1(2) . . ?
C15 C14 C13 116.87(19) . . ?
C15 C14 C18 121.6(2) . . ?
C13 C14 C18 121.5(2) . . ?
C14 C15 C16 122.7(2) . . ?
C15 C16 C11 120.44(19) . . ?
C15 C16 C19 115.08(18) . . ?
C11 C16 C19 124.48(18) . . ?
C25 C20 C21 115.95(17) . . ?
C25 C20 B1 125.92(17) . . ?
C21 C20 B1 117.84(16) . . ?
C22 C21 C20 120.50(19) . . ?
C22 C21 C26 115.72(19) . . ?
C20 C21 C26 123.76(18) . . ?
C23 C22 C21 123.0(2) . . ?
C24 C23 C22 116.50(18) . . ?
C24 C23 C27 121.2(2) . . ?
C22 C23 C27 122.3(2) . . ?
C23 C24 C25 122.77(19) . . ?
C24 C25 C20 121.10(19) . . ?
C24 C25 C28 116.00(18) . . ?
C20 C25 C28 122.90(17) . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.055

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.002 0.000 0.500 281 28 ' '
2 -0.036 0.500 0.000 281 28 ' '
_platon_squeeze_details          
; A disordered hexane solvent molecule was removed 
;

####################################################################### 
# 
# 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_hl9
_database_code_depnum_ccdc_archive 'CCDC 1847801'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 B N'
_chemical_formula_weight         311.21

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   19.0048(7)
_cell_length_b                   7.9860(3)
_cell_length_c                   23.0446(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3497.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2731
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.02

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  0.780
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27021
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         27.138
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3865
_reflns_number_gt                2341
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0445P)²+0.6619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3865
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1105
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.45005(8) 0.48893(19) 0.35581(7) 0.0295(4) Uani 1 1 d . . . . .
C1 C 0.42216(10) 0.7693(2) 0.40680(9) 0.0319(5) Uani 1 1 d . . . . .
C2 C 0.43411(11) 0.8452(3) 0.46075(9) 0.0369(5) Uani 1 1 d . . . . .
H2 H 0.4743 0.8125 0.4824 0.044 Uiso 1 1 calc R U . . .
C3 C 0.39021(11) 0.9650(3) 0.48374(10) 0.0463(6) Uani 1 1 d . . . . .
H3 H 0.3997 1.0113 0.5209 0.056 Uiso 1 1 calc R U . . .
C4 C 0.33253(12) 1.0172(3) 0.45263(11) 0.0528(7) Uani 1 1 d . . . . .
H4 H 0.3015 1.0983 0.4686 0.063 Uiso 1 1 calc R U . . .
C5 C 0.31988(11) 0.9517(3) 0.39819(11) 0.0478(6) Uani 1 1 d . . . . .
H5 H 0.2809 0.9915 0.3763 0.057 Uiso 1 1 calc R U . . .
C6 C 0.36343(10) 0.8275(3) 0.37463(9) 0.0349(5) Uani 1 1 d . . . . .
C7 C 0.34885(9) 0.7704(3) 0.31426(9) 0.0351(5) Uani 1 1 d . . . . .
C8 C 0.33242(10) 0.8884(3) 0.27147(10) 0.0433(6) Uani 1 1 d . . . . .
H8 H 0.3297 1.0034 0.2817 0.052 Uiso 1 1 calc R U . . .
C9 C 0.32014(11) 0.8413(3) 0.21470(11) 0.0486(6) Uani 1 1 d . . . . .
H9 H 0.3102 0.9236 0.1861 0.058 Uiso 1 1 calc R U . . .
C10 C 0.32233(11) 0.6734(3) 0.19972(11) 0.0472(6) Uani 1 1 d . . . . .
H10 H 0.3134 0.6398 0.1609 0.057 Uiso 1 1 calc R U . . .
C11 C 0.33756(10) 0.5553(3) 0.24164(10) 0.0413(6) Uani 1 1 d . . . . .
H11 H 0.3382 0.4402 0.2313 0.050 Uiso 1 1 calc R U . . .
C12 C 0.35206(9) 0.6011(3) 0.29866(9) 0.0331(5) Uani 1 1 d . . . . .
C13 C 0.37430(10) 0.4731(3) 0.34310(10) 0.0369(5) Uani 1 1 d . . . . .
H13A H 0.3469 0.4894 0.3792 0.044 Uiso 1 1 calc R U . . .
H13B H 0.3643 0.3592 0.3283 0.044 Uiso 1 1 calc R U . . .
C14 C 0.49582(10) 0.3525(2) 0.33419(9) 0.0338(5) Uani 1 1 d . . . . .
H14 H 0.5456 0.3895 0.3401 0.041 Uiso 1 1 calc R U . . .
C15 C 0.48608(13) 0.1922(3) 0.36905(11) 0.0518(6) Uani 1 1 d . . . . .
H15A H 0.4383 0.1494 0.3632 0.078 Uiso 1 1 calc R U . . .
H15B H 0.4935 0.2157 0.4103 0.078 Uiso 1 1 calc R U . . .
H15C H 0.5202 0.1082 0.3560 0.078 Uiso 1 1 calc R U . . .
C16 C 0.48668(11) 0.3195(3) 0.26972(9) 0.0399(5) Uani 1 1 d . . . . .
H16A H 0.4898 0.4255 0.2484 0.060 Uiso 1 1 calc R U . . .
H16B H 0.4406 0.2683 0.2628 0.060 Uiso 1 1 calc R U . . .
H16C H 0.5238 0.2436 0.2563 0.060 Uiso 1 1 calc R U . . .
C17 C 0.55482(10) 0.6384(2) 0.40496(8) 0.0294(4) Uani 1 1 d . . . . .
C18 C 0.60103(10) 0.7543(2) 0.38064(9) 0.0315(5) Uani 1 1 d . . . . .
H18 H 0.5839 0.8311 0.3526 0.038 Uiso 1 1 calc R U . . .
C19 C 0.67145(10) 0.7603(3) 0.39636(10) 0.0370(5) Uani 1 1 d . . . . .
H19 H 0.7018 0.8398 0.3786 0.044 Uiso 1 1 calc R U . . .
C20 C 0.69754(11) 0.6518(3) 0.43748(9) 0.0393(5) Uani 1 1 d . . . . .
H20 H 0.7458 0.6561 0.4482 0.047 Uiso 1 1 calc R U . . .
C21 C 0.65331(11) 0.5376(3) 0.46290(10) 0.0470(6) Uani 1 1 d . . . . .
H21 H 0.6707 0.4630 0.4916 0.056 Uiso 1 1 calc R U . . .
C22 C 0.58328(11) 0.5313(3) 0.44656(10) 0.0437(6) Uani 1 1 d . . . . .
H22 H 0.5535 0.4509 0.4644 0.052 Uiso 1 1 calc R U . . .
B1 B 0.47452(11) 0.6275(3) 0.38669(10) 0.0294(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 B1 1.396(3) . ?
N1 C13 1.474(2) . ?
N1 C14 1.481(2) . ?
C1 C2 1.402(3) . ?
C1 C6 1.418(3) . ?
C1 B1 1.577(3) . ?
C2 C3 1.375(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.401(3) . ?
C6 C7 1.490(3) . ?
C7 C8 1.399(3) . ?
C7 C12 1.400(3) . ?
C8 C9 1.381(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.507(3) . ?
C14 C16 1.519(3) . ?
C14 C15 1.523(3) . ?
C17 C18 1.393(3) . ?
C17 C22 1.394(3) . ?
C17 B1 1.585(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.376(3) . ?
C20 C21 1.372(3) . ?
C21 C22 1.384(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
B1 N1 C13 119.65(16) . . ?
B1 N1 C14 124.02(16) . . ?
C13 N1 C14 116.33(16) . . ?
C2 C1 C6 116.69(18) . . ?
C2 C1 B1 117.96(18) . . ?
C6 C1 B1 125.34(18) . . ?
C3 C2 C1 123.0(2) . . ?
C4 C3 C2 119.6(2) . . ?
C3 C4 C5 119.9(2) . . ?
C4 C5 C6 121.2(2) . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 117.95(19) . . ?
C1 C6 C7 122.26(17) . . ?
C8 C7 C12 118.6(2) . . ?
C8 C7 C6 119.55(19) . . ?
C12 C7 C6 121.8(2) . . ?
C9 C8 C7 121.5(2) . . ?
C8 C9 C10 119.6(2) . . ?
C11 C10 C9 119.6(2) . . ?
C10 C11 C12 121.5(2) . . ?
C11 C12 C7 119.2(2) . . ?
C11 C12 C13 121.26(19) . . ?
C7 C12 C13 119.51(19) . . ?
N1 C13 C12 110.52(16) . . ?
N1 C14 C16 112.92(16) . . ?
N1 C14 C15 111.70(17) . . ?
C16 C14 C15 110.90(18) . . ?
C18 C17 C22 116.07(18) . . ?
C18 C17 B1 122.43(18) . . ?
C22 C17 B1 121.50(18) . . ?
C19 C18 C17 121.75(19) . . ?
C20 C19 C18 120.34(19) . . ?
C21 C20 C19 119.47(19) . . ?
C20 C21 C22 119.8(2) . . ?
C21 C22 C17 122.5(2) . . ?
N1 B1 C1 120.59(17) . . ?
N1 B1 C17 119.97(18) . . ?
C1 B1 C17 119.34(17) . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_hl10
_database_code_depnum_ccdc_archive 'CCDC 1847799'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 B N'
_chemical_formula_weight         311.21

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.0764(16)
_cell_length_b                   13.7022(14)
_cell_length_c                   9.8458(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.47
_cell_angle_gamma                90
_cell_volume                     1779.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3791
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      23.80

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.780
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16761
_diffrn_reflns_av_unetI/netI     0.1707
_diffrn_reflns_av_R_equivalents  0.1723
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.973
_diffrn_reflns_theta_max         27.200
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.848
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.848
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.848
_reflns_number_total             3451
_reflns_number_gt                1574
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0901P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3451
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2138
_refine_ls_R_factor_gt           0.0984
_refine_ls_wR_factor_ref         0.2329
_refine_ls_wR_factor_gt          0.1815
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.2614(3) 0.4233(3) 0.6404(4) 0.0379(9) Uani 1 1 d . . . . .
N1 N 0.19094(19) 0.3433(2) 0.6825(3) 0.0366(7) Uani 1 1 d . . . . .
C1 C 0.3543(2) 0.3504(3) 0.6551(4) 0.0398(8) Uani 1 1 d . . . . .
C2 C 0.4444(3) 0.3597(3) 0.6291(4) 0.0484(9) Uani 1 1 d . . . . .
H2 H 0.4619 0.4210 0.5994 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5094(3) 0.2813(3) 0.6459(5) 0.0594(11) Uani 1 1 d . . . . .
H3 H 0.5706 0.2893 0.6267 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4866(3) 0.1914(3) 0.6902(5) 0.0627(12) Uani 1 1 d . . . . .
H4 H 0.5332 0.1389 0.7042 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3969(3) 0.1774(3) 0.7143(4) 0.0537(10) Uani 1 1 d . . . . .
H5 H 0.3797 0.1155 0.7425 0.064 Uiso 1 1 calc R U . . .
C6 C 0.3325(2) 0.2573(3) 0.6957(4) 0.0421(9) Uani 1 1 d . . . . .
C7 C 0.2357(2) 0.2598(3) 0.7143(4) 0.0413(9) Uani 1 1 d . . . . .
H7 H 0.2075 0.2055 0.7468 0.050 Uiso 1 1 calc R U . . .
C8 C 0.0962(2) 0.3660(3) 0.7100(4) 0.0419(9) Uani 1 1 d . . . . .
H8 H 0.0759 0.4342 0.6763 0.050 Uiso 1 1 calc R U . . .
C9 C 0.0091(3) 0.2990(3) 0.6279(4) 0.0512(10) Uani 1 1 d . . . . .
H9A H -0.0010 0.3010 0.5243 0.077 Uiso 1 1 calc R U . . .
H9B H -0.0529 0.3206 0.6426 0.077 Uiso 1 1 calc R U . . .
H9C H 0.0251 0.2320 0.6638 0.077 Uiso 1 1 calc R U . . .
C10 C 0.1181(3) 0.3627(3) 0.8728(4) 0.0519(10) Uani 1 1 d . . . . .
H10A H 0.0566 0.3796 0.8925 0.078 Uiso 1 1 calc R U . . .
H10B H 0.1719 0.4095 0.9215 0.078 Uiso 1 1 calc R U . . .
H10C H 0.1401 0.2968 0.9091 0.078 Uiso 1 1 calc R U . . .
C11 C 0.2815(2) 0.5088(2) 0.7592(4) 0.0376(8) Uani 1 1 d . . . . .
C12 C 0.3516(3) 0.4988(3) 0.8988(4) 0.0432(9) Uani 1 1 d . . . . .
H12 H 0.3920 0.4414 0.9222 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3652(3) 0.5695(3) 1.0055(4) 0.0518(10) Uani 1 1 d . . . . .
H13 H 0.4137 0.5601 1.0998 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3077(3) 0.6527(3) 0.9730(4) 0.0528(10) Uani 1 1 d . . . . .
H14 H 0.3165 0.7015 1.0449 0.063 Uiso 1 1 calc R U . . .
C16 C 0.2248(3) 0.5943(3) 0.7307(4) 0.0461(9) Uani 1 1 d . . . . .
H16 H 0.1762 0.6045 0.6366 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2376(3) 0.6656(3) 0.8371(4) 0.0543(10) Uani 1 1 d . . . . .
H15 H 0.1975 0.7232 0.8151 0.065 Uiso 1 1 calc R U . . .
C17 C 0.2101(3) 0.4617(2) 0.4751(4) 0.0398(8) Uani 1 1 d . . . . .
C18 C 0.2675(3) 0.5259(3) 0.4240(4) 0.0520(10) Uani 1 1 d . . . . .
H18 H 0.3312 0.5477 0.4891 0.062 Uiso 1 1 calc R U . . .
C19 C 0.2346(3) 0.5588(3) 0.2815(4) 0.0562(11) Uani 1 1 d . . . . .
H19 H 0.2760 0.6016 0.2502 0.067 Uiso 1 1 calc R U . . .
C20 C 0.1426(4) 0.5294(3) 0.1863(4) 0.0546(11) Uani 1 1 d . . . . .
H20 H 0.1199 0.5514 0.0887 0.066 Uiso 1 1 calc R U . . .
C21 C 0.0832(3) 0.4681(3) 0.2325(4) 0.0524(10) Uani 1 1 d . . . . .
H21 H 0.0188 0.4481 0.1670 0.063 Uiso 1 1 calc R U . . .
C22 C 0.1169(3) 0.4351(2) 0.3752(4) 0.0415(9) Uani 1 1 d . . . . .
H22 H 0.0746 0.3927 0.4051 0.050 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
B1 C11 1.609(5) . ?
B1 C1 1.612(5) . ?
B1 C17 1.620(5) . ?
B1 N1 1.626(5) . ?
N1 C7 1.291(4) . ?
N1 C8 1.484(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.403(5) . ?
C2 C3 1.383(5) . ?
C3 C4 1.382(6) . ?
C4 C5 1.377(6) . ?
C5 C6 1.392(5) . ?
C6 C7 1.437(5) . ?
C8 C9 1.518(5) . ?
C8 C10 1.524(5) . ?
C11 C16 1.388(5) . ?
C11 C12 1.391(5) . ?
C12 C13 1.392(5) . ?
C13 C14 1.370(5) . ?
C14 C15 1.368(5) . ?
C16 C15 1.398(5) . ?
C17 C22 1.385(5) . ?
C17 C18 1.401(5) . ?
C18 C19 1.390(5) . ?
C19 C20 1.368(6) . ?
C20 C21 1.370(6) . ?
C21 C22 1.392(5) . ?

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
C11 B1 C1 117.1(3) . . ?
C11 B1 C17 113.4(3) . . ?
C1 B1 C17 110.7(3) . . ?
C11 B1 N1 105.9(3) . . ?
C1 B1 N1 96.1(3) . . ?
C17 B1 N1 112.2(3) . . ?
C7 N1 C8 122.3(3) . . ?
C7 N1 B1 111.7(3) . . ?
C8 N1 B1 124.9(3) . . ?
C2 C1 C6 116.2(3) . . ?
C2 C1 B1 133.9(3) . . ?
C6 C1 B1 109.8(3) . . ?
C3 C2 C1 121.1(4) . . ?
C4 C3 C2 120.9(4) . . ?
C5 C4 C3 120.4(4) . . ?
C4 C5 C6 117.5(4) . . ?
C5 C6 C1 123.8(3) . . ?
C5 C6 C7 127.2(4) . . ?
C1 C6 C7 109.0(3) . . ?
N1 C7 C6 113.2(3) . . ?
N1 C8 C9 112.7(3) . . ?
N1 C8 C10 108.7(3) . . ?
C9 C8 C10 111.8(3) . . ?
C16 C11 C12 116.2(3) . . ?
C16 C11 B1 121.6(3) . . ?
C12 C11 B1 122.0(3) . . ?
C11 C12 C13 122.7(4) . . ?
C14 C13 C12 119.3(4) . . ?
C15 C14 C13 120.1(4) . . ?
C11 C16 C15 121.6(3) . . ?
C14 C15 C16 120.2(4) . . ?
C22 C17 C18 115.6(3) . . ?
C22 C17 B1 127.4(3) . . ?
C18 C17 B1 117.0(3) . . ?
C19 C18 C17 122.4(4) . . ?
C20 C19 C18 119.8(4) . . ?
C19 C20 C21 119.7(4) . . ?
C20 C21 C22 120.1(4) . . ?
C17 C22 C21 122.4(4) . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.184
_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_hl8
_database_code_depnum_ccdc_archive 'CCDC 1847800'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H41 B N'
_chemical_formula_weight         474.49

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.9902(4)
_cell_length_b                   21.3281(10)
_cell_length_c                   17.0355(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.778(2)
_cell_angle_gamma                90
_cell_volume                     2831.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7390
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.32

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_F_000             1028
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.063
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            96859
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.1388
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.269
_diffrn_reflns_theta_max         27.136
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6245
_reflns_number_gt                3353
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0700P)²+1.3200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0058(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6245
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.003
_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 0.4444(4) 0.61990(13) 0.70739(17) 0.0370(6) Uani 1 1 d . . . . .
C1 C 0.4755(3) 0.69394(11) 0.71254(15) 0.0420(6) Uani 1 1 d . . . . .
H1A H 0.4273 0.7113 0.6584 0.050 Uiso 1 1 calc R U . . .
H1B H 0.4057 0.7110 0.7489 0.050 Uiso 1 1 calc R U . . .
N1 N 0.5313(3) 0.57659(9) 0.76308(11) 0.0369(5) Uani 1 1 d . . . . .
C2 C 0.6549(3) 0.72040(11) 0.74005(16) 0.0415(6) Uani 1 1 d . . . . .
C3 C 0.7458(3) 0.73949(12) 0.68375(16) 0.0474(7) Uani 1 1 d . . . . .
H3 H 0.6949 0.7351 0.6281 0.057 Uiso 1 1 calc R U . . .
C4 C 0.9090(4) 0.76480(13) 0.70660(18) 0.0539(7) Uani 1 1 d . . . . .
C5 C 0.9814(4) 0.77039(13) 0.78772(18) 0.0533(7) Uani 1 1 d . . . . .
H5 H 1.0935 0.7875 0.8040 0.064 Uiso 1 1 calc R U . . .
C6 C 0.8956(4) 0.75190(12) 0.84610(17) 0.0481(7) Uani 1 1 d . . . . .
C7 C 0.7305(3) 0.72714(11) 0.82185(15) 0.0423(6) Uani 1 1 d . . . . .
C8 C 0.9836(4) 0.75666(14) 0.93408(17) 0.0590(8) Uani 1 1 d . . . . .
H8A H 1.0886 0.7816 0.9397 0.088 Uiso 1 1 calc R U . . .
H8B H 1.0129 0.7145 0.9558 0.088 Uiso 1 1 calc R U . . .
H8C H 0.9065 0.7769 0.9638 0.088 Uiso 1 1 calc R U . . .
C9 C 1.0043(5) 0.78473(19) 0.6437(2) 0.0798(11) Uani 1 1 d . . . . .
H9A H 1.0870 0.8176 0.6658 0.120 Uiso 1 1 calc R U . . .
H9B H 0.9225 0.8009 0.5965 0.120 Uiso 1 1 calc R U . . .
H9C H 1.0652 0.7486 0.6279 0.120 Uiso 1 1 calc R U . . .
C10 C 0.6316(3) 0.70588(13) 0.88121(15) 0.0444(6) Uani 1 1 d . . . . .
C11 C 0.5957(3) 0.64211(12) 0.88759(15) 0.0432(6) Uani 1 1 d . . . . .
C12 C 0.4978(4) 0.62338(15) 0.94151(16) 0.0543(7) Uani 1 1 d . . . . .
H12 H 0.4754 0.5801 0.9474 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4325(4) 0.66718(18) 0.98668(18) 0.0637(9) Uani 1 1 d . . . . .
H13 H 0.3658 0.6538 1.0233 0.076 Uiso 1 1 calc R U . . .
C14 C 0.4636(4) 0.73024(17) 0.97881(18) 0.0633(9) Uani 1 1 d . . . . .
H14 H 0.4163 0.7603 1.0089 0.076 Uiso 1 1 calc R U . . .
C15 C 0.5633(4) 0.74924(14) 0.92725(17) 0.0541(7) Uani 1 1 d . . . . .
H15 H 0.5865 0.7926 0.9227 0.065 Uiso 1 1 calc R U . . .
C16 C 0.6619(3) 0.59427(12) 0.83627(14) 0.0413(6) Uani 1 1 d . . . . .
H16A H 0.7639 0.6116 0.8198 0.050 Uiso 1 1 calc R U . . .
H16B H 0.6983 0.5562 0.8688 0.050 Uiso 1 1 calc R U . . .
C17 C 0.2973(3) 0.59955(10) 0.63287(14) 0.0344(5) Uani 1 1 d . . . . .
C18 C 0.3340(3) 0.59083(11) 0.55655(14) 0.0374(6) Uani 1 1 d . . . . .
C19 C 0.2004(3) 0.58164(12) 0.48917(15) 0.0423(6) Uani 1 1 d . . . . .
H19 H 0.2272 0.5757 0.4381 0.051 Uiso 1 1 calc R U . . .
C20 C 0.0305(3) 0.58099(12) 0.49476(16) 0.0447(6) Uani 1 1 d . . . . .
C21 C -0.0044(3) 0.58854(12) 0.56995(16) 0.0440(6) Uani 1 1 d . . . . .
H21 H -0.1205 0.5877 0.5749 0.053 Uiso 1 1 calc R U . . .
C22 C 0.1244(3) 0.59734(11) 0.63885(15) 0.0389(6) Uani 1 1 d . . . . .
C23 C 0.0765(4) 0.60341(14) 0.71932(17) 0.0535(7) Uani 1 1 d . . . . .
H23A H -0.0390 0.6212 0.7117 0.080 Uiso 1 1 calc R U . . .
H23B H 0.1588 0.6310 0.7543 0.080 Uiso 1 1 calc R U . . .
H23C H 0.0786 0.5619 0.7443 0.080 Uiso 1 1 calc R U . . .
C24 C 0.5165(3) 0.59082(14) 0.54710(16) 0.0486(7) Uani 1 1 d . . . . .
H24A H 0.5705 0.5507 0.5658 0.073 Uiso 1 1 calc R U . . .
H24B H 0.5797 0.6250 0.5791 0.073 Uiso 1 1 calc R U . . .
H24C H 0.5184 0.5968 0.4903 0.073 Uiso 1 1 calc R U . . .
C25 C -0.1118(4) 0.57335(14) 0.42059(17) 0.0591(8) Uani 1 1 d . . . . .
H25A H -0.1903 0.5402 0.4299 0.089 Uiso 1 1 calc R U . . .
H25B H -0.0627 0.5619 0.3747 0.089 Uiso 1 1 calc R U . . .
H25C H -0.1749 0.6129 0.4091 0.089 Uiso 1 1 calc R U . . .
C26 C 0.5067(3) 0.50812(11) 0.75128(15) 0.0394(6) Uani 1 1 d . . . . .
H26 H 0.4179 0.5025 0.7003 0.047 Uiso 1 1 calc R U . . .
C27 C 0.6685(3) 0.47580(12) 0.73851(16) 0.0446(6) Uani 1 1 d . . . . .
H27A H 0.7609 0.4803 0.7876 0.053 Uiso 1 1 calc R U . . .
H27B H 0.7072 0.4962 0.6934 0.053 Uiso 1 1 calc R U . . .
C28 C 0.6355(4) 0.40636(13) 0.71985(17) 0.0559(8) Uani 1 1 d . . . . .
H28A H 0.5519 0.4018 0.6678 0.067 Uiso 1 1 calc R U . . .
H28B H 0.7438 0.3858 0.7150 0.067 Uiso 1 1 calc R U . . .
C29 C 0.5661(4) 0.37463(13) 0.78557(18) 0.0576(8) Uani 1 1 d . . . . .
H29A H 0.5401 0.3302 0.7708 0.069 Uiso 1 1 calc R U . . .
H29B H 0.6549 0.3754 0.8363 0.069 Uiso 1 1 calc R U . . .
C30 C 0.4057(4) 0.40640(12) 0.79882(18) 0.0522(7) Uani 1 1 d . . . . .
H30A H 0.3682 0.3860 0.8442 0.063 Uiso 1 1 calc R U . . .
H30B H 0.3127 0.4016 0.7501 0.063 Uiso 1 1 calc R U . . .
C31 C 0.4376(3) 0.47595(12) 0.81718(16) 0.0453(6) Uani 1 1 d . . . . .
H31A H 0.3290 0.4963 0.8220 0.054 Uiso 1 1 calc R U . . .
H31B H 0.5211 0.4807 0.8692 0.054 Uiso 1 1 calc R U . . .
C32 C 0.0136(5) 0.56368(17) 0.0067(2) 0.0722(9) Uani 1 1 d . . . . .
H32A H 0.0234 0.6080 0.0115 0.087 Uiso 1 1 calc R U . . .
C33 C -0.0717(4) 0.53104(18) 0.0546(2) 0.0722(10) Uani 1 1 d . . . . .
H33A H -0.1220 0.5525 0.0925 0.108 Uiso 1 1 calc R U . . .
C34 C 0.0846(4) 0.53299(18) -0.0479(2) 0.0703(9) Uani 1 1 d . . . . .
H34A H 0.1433 0.5559 -0.0814 0.105 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
B1 N1 1.394(3) . ?
B1 C17 1.588(4) . ?
B1 C1 1.598(4) . ?
C1 C2 1.515(3) . ?
N1 C26 1.481(3) . ?
N1 C16 1.487(3) . ?
C2 C3 1.386(4) . ?
C2 C7 1.398(3) . ?
C3 C4 1.385(4) . ?
C4 C5 1.380(4) . ?
C4 C9 1.506(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.396(4) . ?
C6 C8 1.512(4) . ?
C7 C10 1.485(4) . ?
C10 C11 1.399(4) . ?
C10 C15 1.399(4) . ?
C11 C12 1.391(4) . ?
C11 C16 1.513(4) . ?
C12 C13 1.384(4) . ?
C13 C14 1.380(5) . ?
C14 C15 1.371(4) . ?
C17 C18 1.407(3) . ?
C17 C22 1.408(3) . ?
C18 C19 1.398(3) . ?
C18 C24 1.503(4) . ?
C19 C20 1.382(4) . ?
C20 C21 1.379(4) . ?
C20 C25 1.510(3) . ?
C21 C22 1.392(3) . ?
C22 C23 1.508(4) . ?
C26 C31 1.520(3) . ?
C26 C27 1.523(4) . ?
C27 C28 1.526(4) . ?
C28 C29 1.514(4) . ?
C29 C30 1.511(4) . ?
C30 C31 1.526(4) . ?
C32 C34 1.360(5) . ?
C32 C33 1.364(5) . ?
C33 C34 1.372(5) 3_565 ?
C34 C33 1.372(5) 3_565 ?

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 C17 122.1(2) . . ?
N1 B1 C1 124.7(2) . . ?
C17 B1 C1 113.1(2) . . ?
C2 C1 B1 120.6(2) . . ?
B1 N1 C26 122.0(2) . . ?
B1 N1 C16 123.6(2) . . ?
C26 N1 C16 114.28(18) . . ?
C3 C2 C7 118.8(2) . . ?
C3 C2 C1 120.0(2) . . ?
C7 C2 C1 121.2(2) . . ?
C4 C3 C2 121.7(3) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 C9 121.5(3) . . ?
C3 C4 C9 120.2(3) . . ?
C4 C5 C6 122.0(3) . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 C8 119.8(2) . . ?
C7 C6 C8 121.4(3) . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 C10 121.6(2) . . ?
C2 C7 C10 118.0(2) . . ?
C11 C10 C15 119.2(3) . . ?
C11 C10 C7 119.9(2) . . ?
C15 C10 C7 120.8(3) . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 C16 120.5(2) . . ?
C10 C11 C16 120.5(2) . . ?
C13 C12 C11 120.6(3) . . ?
C14 C13 C12 120.4(3) . . ?
C15 C14 C13 119.6(3) . . ?
C14 C15 C10 121.2(3) . . ?
N1 C16 C11 112.7(2) . . ?
C18 C17 C22 118.1(2) . . ?
C18 C17 B1 120.4(2) . . ?
C22 C17 B1 121.1(2) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 C24 119.7(2) . . ?
C17 C18 C24 120.3(2) . . ?
C20 C19 C18 121.9(2) . . ?
C21 C20 C19 117.8(2) . . ?
C21 C20 C25 121.3(3) . . ?
C19 C20 C25 120.9(3) . . ?
C20 C21 C22 122.3(2) . . ?
C21 C22 C17 119.9(2) . . ?
C21 C22 C23 119.3(2) . . ?
C17 C22 C23 120.9(2) . . ?
N1 C26 C31 113.8(2) . . ?
N1 C26 C27 112.0(2) . . ?
C31 C26 C27 111.1(2) . . ?
C26 C27 C28 110.9(2) . . ?
C29 C28 C27 110.8(2) . . ?
C30 C29 C28 111.8(2) . . ?
C29 C30 C31 111.0(2) . . ?
C26 C31 C30 111.1(2) . . ?
C34 C32 C33 120.2(3) . . ?
C32 C33 C34 119.7(3) . 3_565 ?
C32 C34 C33 120.1(3) . 3_565 ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.050

