# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1843607'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            borazatruxene
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 B3 N3'
_chemical_formula_sum            'C21 H18 B3 N3'
_chemical_formula_weight         344.81

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                   5.13460(10)
_cell_length_b                   14.3862(3)
_cell_length_c                   23.4929(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.5300(9)
_cell_angle_gamma                90
_cell_volume                     1734.74(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    29976
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      27.485

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  1.003
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       '481 1.1 degree images with φ and ω scans'
_diffrn_reflns_number            22750
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.962
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3982
_reflns_number_gt                2435
_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2013 (Sheldrick, 2013)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'SHELXL-2013 (Sheldrick, 2013)
;

_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)+(0.0653P)²+0.0094P] 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         3982
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 -0.1532(2) 0.51638(9) 0.25707(5) 0.0274(3) Uani 1 1 d . . . . .
N2 N 0.1267(3) 0.40207(9) 0.21078(6) 0.0273(3) Uani 1 1 d . . . . .
N3 N -0.1916(3) 0.49221(10) 0.15355(6) 0.0279(3) Uani 1 1 d . . . . .
B1 B 0.0558(4) 0.44937(13) 0.26122(8) 0.0269(5) Uani 1 1 d . . . . .
B2 B 0.0089(4) 0.42460(14) 0.15582(8) 0.0271(4) Uani 1 1 d . . . . .
B3 B -0.2782(4) 0.53832(13) 0.20423(8) 0.0274(5) Uani 1 1 d . . . . .
C1 C -0.1880(3) 0.56237(12) 0.31234(7) 0.0296(4) Uani 1 1 d . . . . .
H1A H -0.3675 0.5532 0.3257 0.036 Uiso 1 1 calc R U . . .
H1B H -0.1531 0.6299 0.3095 0.036 Uiso 1 1 calc R U . . .
C2 C 0.0076(3) 0.51615(12) 0.35222(7) 0.0276(4) Uani 1 1 d . . . . .
C3 C 0.0481(3) 0.53468(13) 0.40969(7) 0.0337(4) Uani 1 1 d . . . . .
H3 H -0.0517 0.5809 0.4281 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2370(3) 0.48449(13) 0.43991(7) 0.0369(5) Uani 1 1 d . . . . .
H4 H 0.2655 0.4962 0.4794 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3851(3) 0.41720(13) 0.41303(7) 0.0341(4) Uani 1 1 d . . . . .
H5 H 0.5147 0.3838 0.4342 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3444(3) 0.39893(12) 0.35573(7) 0.0299(4) Uani 1 1 d . . . . .
H6 H 0.4447 0.3526 0.3376 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1554(3) 0.44865(11) 0.32440(7) 0.0266(4) Uani 1 1 d . . . . .
C8 C 0.3360(3) 0.33344(12) 0.20496(7) 0.0289(4) Uani 1 1 d . . . . .
H8A H 0.2995 0.2767 0.2272 0.035 Uiso 1 1 calc R U . . .
H8B H 0.5056 0.3595 0.2182 0.035 Uiso 1 1 calc R U . . .
C9 C 0.3373(3) 0.31212(12) 0.14175(7) 0.0283(4) Uani 1 1 d . . . . .
C10 C 0.5026(3) 0.25093(12) 0.11456(7) 0.0329(4) Uani 1 1 d . . . . .
H10 H 0.6323 0.2174 0.1356 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4739(4) 0.23983(13) 0.05602(8) 0.0372(5) Uani 1 1 d . . . . .
H11 H 0.5849 0.1981 0.0368 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2847(4) 0.28906(13) 0.02525(7) 0.0369(5) Uani 1 1 d . . . . .
H12 H 0.2660 0.2802 -0.0147 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1232(3) 0.35092(13) 0.05248(7) 0.0335(4) Uani 1 1 d . . . . .
H13 H -0.0043 0.3850 0.0311 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1480(3) 0.36328(11) 0.11142(7) 0.0275(4) Uani 1 1 d . . . . .
C15 C -0.3317(3) 0.52833(12) 0.10273(7) 0.0295(4) Uani 1 1 d . . . . .
H15A H -0.4252 0.4777 0.0822 0.035 Uiso 1 1 calc R U . . .
H15B H -0.2096 0.5582 0.0765 0.035 Uiso 1 1 calc R U . . .
C16 C -0.5209(3) 0.59838(12) 0.12540(7) 0.0283(4) Uani 1 1 d . . . . .
C17 C -0.6989(3) 0.65196(12) 0.09408(8) 0.0339(4) Uani 1 1 d . . . . .
H17 H -0.7092 0.6474 0.0537 0.041 Uiso 1 1 calc R U . . .
C18 C -0.8611(3) 0.71205(12) 0.12266(8) 0.0346(5) Uani 1 1 d . . . . .
H18 H -0.9809 0.7499 0.1016 0.041 Uiso 1 1 calc R U . . .
C19 C -0.8505(3) 0.71753(12) 0.18141(8) 0.0330(4) Uani 1 1 d . . . . .
H19 H -0.9662 0.7578 0.2004 0.040 Uiso 1 1 calc R U . . .
C20 C -0.6734(3) 0.66498(12) 0.21258(7) 0.0296(4) Uani 1 1 d . . . . .
H20 H -0.6679 0.6691 0.2530 0.036 Uiso 1 1 calc R U . . .
C21 C -0.5017(3) 0.60559(11) 0.18504(7) 0.0276(4) 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 B3 1.418(2) . ?
N1 B1 1.444(2) . ?
N1 C1 1.472(2) . ?
N2 B1 1.422(2) . ?
N2 B2 1.448(2) . ?
N2 C8 1.468(2) . ?
N3 B2 1.416(2) . ?
N3 B3 1.444(2) . ?
N3 C15 1.472(2) . ?
B1 C7 1.557(2) . ?
B2 C14 1.554(3) . ?
B3 C21 1.559(3) . ?
C1 C2 1.509(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.386(2) . ?
C2 C7 1.405(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.517(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.390(2) . ?
C9 C14 1.399(2) . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.507(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.391(2) . ?
C16 C21 1.406(2) . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(2) . ?
C20 H20 0.9500 . ?

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
B3 N1 B1 121.73(14) . . ?
B3 N1 C1 127.54(14) . . ?
B1 N1 C1 110.37(13) . . ?
B1 N2 B2 121.72(14) . . ?
B1 N2 C8 127.12(13) . . ?
B2 N2 C8 110.90(13) . . ?
B2 N3 B3 121.61(14) . . ?
B2 N3 C15 127.74(14) . . ?
B3 N3 C15 110.60(13) . . ?
N2 B1 N1 118.01(15) . . ?
N2 B1 C7 134.93(16) . . ?
N1 B1 C7 107.06(14) . . ?
N3 B2 N2 118.25(16) . . ?
N3 B2 C14 135.31(16) . . ?
N2 B2 C14 106.44(15) . . ?
N1 B3 N3 118.53(16) . . ?
N1 B3 C21 134.76(16) . . ?
N3 B3 C21 106.71(14) . . ?
N1 C1 C2 104.77(13) . . ?
N1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C3 C2 C7 121.14(15) . . ?
C3 C2 C1 126.86(16) . . ?
C7 C2 C1 112.00(14) . . ?
C2 C3 C4 118.84(17) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 120.78(16) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.24(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.01(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 118.98(15) . . ?
C6 C7 B1 135.29(15) . . ?
C2 C7 B1 105.73(14) . . ?
N2 C8 C9 104.45(13) . . ?
N2 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
N2 C8 H8B 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C14 121.58(16) . . ?
C10 C9 C8 126.65(16) . . ?
C14 C9 C8 111.77(15) . . ?
C11 C10 C9 118.57(17) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 120.73(17) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.41(17) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.97(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 118.73(16) . . ?
C13 C14 B2 134.87(16) . . ?
C9 C14 B2 106.40(14) . . ?
N3 C15 C16 104.79(13) . . ?
N3 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
N3 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 C21 120.92(16) . . ?
C17 C16 C15 127.18(16) . . ?
C21 C16 C15 111.90(14) . . ?
C18 C17 C16 118.95(17) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 120.74(17) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 120.47(17) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.30(16) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 118.55(15) . . ?
C20 C21 B3 135.55(16) . . ?
C16 C21 B3 105.90(15) . . ?

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
B2 N2 B1 N1 4.7(2) . . . . ?
C8 N2 B1 N1 178.38(14) . . . . ?
B2 N2 B1 C7 -174.13(17) . . . . ?
C8 N2 B1 C7 -0.4(3) . . . . ?
B3 N1 B1 N2 -2.8(2) . . . . ?
C1 N1 B1 N2 -176.42(14) . . . . ?
B3 N1 B1 C7 176.31(14) . . . . ?
C1 N1 B1 C7 2.70(18) . . . . ?
B3 N3 B2 N2 0.2(2) . . . . ?
C15 N3 B2 N2 177.64(14) . . . . ?
B3 N3 B2 C14 -179.67(18) . . . . ?
C15 N3 B2 C14 -2.2(3) . . . . ?
B1 N2 B2 N3 -3.4(2) . . . . ?
C8 N2 B2 N3 -178.02(14) . . . . ?
B1 N2 B2 C14 176.47(14) . . . . ?
C8 N2 B2 C14 1.85(18) . . . . ?
B1 N1 B3 N3 -0.3(2) . . . . ?
C1 N1 B3 N3 172.17(15) . . . . ?
B1 N1 B3 C21 -179.49(17) . . . . ?
C1 N1 B3 C21 -7.1(3) . . . . ?
B2 N3 B3 N1 1.6(2) . . . . ?
C15 N3 B3 N1 -176.25(14) . . . . ?
B2 N3 B3 C21 -178.95(14) . . . . ?
C15 N3 B3 C21 3.17(18) . . . . ?
B3 N1 C1 C2 -175.50(15) . . . . ?
B1 N1 C1 C2 -2.37(18) . . . . ?
N1 C1 C2 C3 -179.13(16) . . . . ?
N1 C1 C2 C7 1.09(18) . . . . ?
C7 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 C4 179.62(16) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C2 -0.6(2) . . . . ?
C5 C6 C7 B1 179.32(17) . . . . ?
C3 C2 C7 C6 0.7(2) . . . . ?
C1 C2 C7 C6 -179.53(14) . . . . ?
C3 C2 C7 B1 -179.29(15) . . . . ?
C1 C2 C7 B1 0.49(18) . . . . ?
N2 B1 C7 C6 -3.0(3) . . . . ?
N1 B1 C7 C6 178.08(17) . . . . ?
N2 B1 C7 C2 176.97(18) . . . . ?
N1 B1 C7 C2 -1.94(18) . . . . ?
B1 N2 C8 C9 -175.68(15) . . . . ?
B2 N2 C8 C9 -1.42(18) . . . . ?
N2 C8 C9 C10 179.75(15) . . . . ?
N2 C8 C9 C14 0.39(19) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C8 C9 C10 C11 179.60(16) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C12 C13 C14 B2 179.56(17) . . . . ?
C10 C9 C14 C13 1.0(2) . . . . ?
C8 C9 C14 C13 -179.57(15) . . . . ?
C10 C9 C14 B2 -178.70(15) . . . . ?
C8 C9 C14 B2 0.69(19) . . . . ?
N3 B2 C14 C13 -1.4(3) . . . . ?
N2 B2 C14 C13 178.79(18) . . . . ?
N3 B2 C14 C9 178.30(19) . . . . ?
N2 B2 C14 C9 -1.54(18) . . . . ?
B2 N3 C15 C16 -179.74(15) . . . . ?
B3 N3 C15 C16 -2.03(17) . . . . ?
N3 C15 C16 C17 -179.97(16) . . . . ?
N3 C15 C16 C21 -0.06(18) . . . . ?
C21 C16 C17 C18 -0.9(2) . . . . ?
C15 C16 C17 C18 178.97(16) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C18 C19 C20 1.7(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C16 -2.3(2) . . . . ?
C19 C20 C21 B3 178.89(17) . . . . ?
C17 C16 C21 C20 2.7(2) . . . . ?
C15 C16 C21 C20 -177.21(14) . . . . ?
C17 C16 C21 B3 -178.16(15) . . . . ?
C15 C16 C21 B3 1.92(18) . . . . ?
N1 B3 C21 C20 -4.9(3) . . . . ?
N3 B3 C21 C20 175.80(17) . . . . ?
N1 B3 C21 C16 176.19(19) . . . . ?
N3 B3 C21 C16 -3.10(18) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_e16gdp3
_database_code_depnum_ccdc_archive 'CCDC 1865474'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2019-02-14 deposited with the CCDC.	2019-08-28 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         'C7 H10 B N'
_chemical_formula_sum            'C7 H10 B N'
_chemical_formula_weight         118.97

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.4509(3)
_cell_length_b                   10.8604(5)
_cell_length_c                   9.7158(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.032(4)
_cell_angle_gamma                90
_cell_volume                     672.24(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2590
_cell_measurement_theta_min      3.9820
_cell_measurement_theta_max      29.1440

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_T_min  0.93214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.906
_oxdiff_exptl_absorpt_empirical_full_max 1.070
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      149.99(11)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            6000
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.550
_diffrn_reflns_theta_max         30.215
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1776
_reflns_number_gt                1488
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    
; 
 SHELXT 
G.M.Sheldrick,Acta Crystallogr.,Sect. A: Found.Crystallogr., 2008, 64,112-122.
;
_computing_structure_refinement  
;
 SHELXL-2014/8 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0571P)²+0.1804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1776
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B 0.4751(2) 0.48191(13) 0.75286(14) 0.0230(3) Uani 1 1 d . . . . .
H1C H 0.319(2) 0.5290(14) 0.7337(15) 0.033(4) Uiso 1 1 d . . . . .
H1D H 0.527(2) 0.4646(13) 0.8668(15) 0.030(4) Uiso 1 1 d . . . . .
N N 0.65037(15) 0.57247(9) 0.70095(11) 0.0225(2) Uani 1 1 d . . . . .
H2A H 0.587(2) 0.6230(15) 0.6308(17) 0.038(4) Uiso 1 1 d . . . . .
H2B H 0.715(3) 0.6255(16) 0.7693(18) 0.044(5) Uiso 1 1 d . . . . .
C1 C 0.80958(17) 0.49394(11) 0.64616(13) 0.0242(3) Uani 1 1 d . . . . .
H1A H 0.9315 0.4780 0.7195 0.029 Uiso 1 1 calc R U . . .
H1B H 0.8595 0.5341 0.5659 0.029 Uiso 1 1 calc R U . . .
C2 C 0.69458(16) 0.37611(10) 0.60197(11) 0.0190(2) Uani 1 1 d . . . . .
C3 C 0.76008(18) 0.28638(11) 0.51613(12) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.8892 0.2951 0.4817 0.028 Uiso 1 1 calc R U . . .
C4 C 0.63367(19) 0.18362(11) 0.48142(13) 0.0265(3) Uani 1 1 d . . . . .
H4 H 0.6751 0.1222 0.4217 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4464(2) 0.17111(11) 0.53446(13) 0.0279(3) Uani 1 1 d . . . . .
H5 H 0.3599 0.1012 0.5103 0.033 Uiso 1 1 calc R U . . .
C6 C 0.38506(17) 0.26037(11) 0.62258(13) 0.0243(3) Uani 1 1 d . . . . .
H6 H 0.2583 0.2498 0.6595 0.029 Uiso 1 1 calc R U . . .
C7 C 0.50733(16) 0.36539(10) 0.65762(11) 0.0193(3) 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
B C7 1.6004(17) . ?
B N 1.6368(16) . ?
B H1C 1.119(14) . ?
B H1D 1.122(14) . ?
N C1 1.4957(15) . ?
N H2A 0.920(17) . ?
N H2B 0.927(18) . ?
C1 C2 1.5075(15) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.3908(16) . ?
C2 C7 1.4036(15) . ?
C3 C4 1.3921(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3925(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3912(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3981(15) . ?
C6 H6 0.9500 . ?

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
C7 B N 97.94(9) . . ?
C7 B H1C 117.4(8) . . ?
N B H1C 108.8(8) . . ?
C7 B H1D 113.1(7) . . ?
N B H1D 106.9(7) . . ?
H1C B H1D 111.3(10) . . ?
C1 N B 108.25(9) . . ?
C1 N H2A 109.1(10) . . ?
B N H2A 109.7(10) . . ?
C1 N H2B 110.8(10) . . ?
B N H2B 114.0(10) . . ?
H2A N H2B 104.9(14) . . ?
N C1 C2 104.52(9) . . ?
N C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
N C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C3 C2 C7 122.26(10) . . ?
C3 C2 C1 125.68(10) . . ?
C7 C2 C1 112.06(10) . . ?
C2 C3 C4 119.04(11) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 119.86(11) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.45(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.95(11) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 117.42(10) . . ?
C6 C7 B 131.78(10) . . ?
C2 C7 B 110.79(10) . . ?

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
C7 B N C1 -24.08(11) . . . . ?
B N C1 C2 24.92(11) . . . . ?
N C1 C2 C3 164.29(11) . . . . ?
N C1 C2 C7 -15.52(12) . . . . ?
C7 C2 C3 C4 1.49(17) . . . . ?
C1 C2 C3 C4 -178.30(11) . . . . ?
C2 C3 C4 C5 -1.02(17) . . . . ?
C3 C4 C5 C6 -0.33(18) . . . . ?
C4 C5 C6 C7 1.26(18) . . . . ?
C5 C6 C7 C2 -0.80(16) . . . . ?
C5 C6 C7 B 179.02(11) . . . . ?
C3 C2 C7 C6 -0.58(16) . . . . ?
C1 C2 C7 C6 179.23(10) . . . . ?
C3 C2 C7 B 179.56(10) . . . . ?
C1 C2 C7 B -0.63(13) . . . . ?
N B C7 C6 -165.10(11) . . . . ?
N B C7 C2 14.73(11) . . . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.197
_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_syn-9
_database_code_depnum_ccdc_archive 'CCDC 1843608'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 B3 N3'
_chemical_formula_sum            'C24 H24 B3 N3'
_chemical_formula_weight         386.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   20.4365(5)
_cell_length_b                   20.4365(5)
_cell_length_c                   8.6540(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3130.12(17)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3787
_cell_measurement_theta_min      4.3180
_cell_measurement_theta_max      72.8630

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.540
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_T_min  0.88943
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.769
_oxdiff_exptl_absorpt_empirical_full_max 1.259
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            7994
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.327
_diffrn_reflns_theta_max         72.930
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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             1383
_reflns_number_gt                1238
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_computing_structure_refinement  
;
 SHELXL-2018/1 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          
;
the compound crystallised out as a 1:1 mixture of enantiomeres.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+1.0391P] 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-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1383
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.3049(2) 0.5868(3) 0.4523(4) 0.0231(7) Uani 0.5 1 d . . P A 1
N1 N 0.38540(13) 0.63958(12) 0.4478(2) 0.0237(3) Uani 0.5 1 d . . P A 1
C1 C 0.29711(10) 0.50637(8) 0.46824(19) 0.0265(6) Uani 0.5 1 d G . P A 1
C2 C 0.23641(7) 0.43352(9) 0.48597(19) 0.0323(4) Uani 0.5 1 d G . P A 1
H2 H 0.186197 0.424819 0.483554 0.039 Uiso 0.5 1 calc R U P A 1
C3 C 0.24917(8) 0.37339(7) 0.5072(3) 0.0415(8) Uani 0.5 1 d G . P A 1
H3 H 0.207679 0.323602 0.519360 0.050 Uiso 0.5 1 calc R U P A 1
C4 C 0.32263(9) 0.38612(7) 0.5108(3) 0.0392(7) Uani 0.5 1 d G . P A 1
H4 H 0.331350 0.345025 0.525315 0.047 Uiso 0.5 1 calc R U P A 1
C5 C 0.38333(7) 0.45897(8) 0.49305(19) 0.0337(4) Uani 0.5 1 d G . P A 1
H5 H 0.433539 0.467664 0.495464 0.040 Uiso 0.5 1 calc R U P A 1
C6 C 0.37057(8) 0.51909(6) 0.47178(17) 0.0269(4) Uani 0.5 1 d G . P A 1
C7 C 0.42980(10) 0.60106(10) 0.45336(19) 0.0255(4) Uani 0.5 1 d . . P A 1
H7 H 0.463545 0.618388 0.546041 0.031 Uiso 0.5 1 calc R U P A 1
C8 C 0.47704(15) 0.61482(15) 0.3074(3) 0.0321(5) Uani 0.5 1 d . . P A 1
H8A H 0.443705 0.597008 0.217064 0.048 Uiso 0.5 1 calc R U P A 1
H8B H 0.504759 0.587285 0.314897 0.048 Uiso 0.5 1 calc R U P A 1
H8C H 0.512963 0.668993 0.296768 0.048 Uiso 0.5 1 calc R U P A 1
B2 B 0.3351(2) 0.5973(2) 0.4527(4) 0.0229(7) Uani 0.5 1 d . . P B 2
N2 N 0.26414(13) 0.59676(9) 0.4483(2) 0.0237(3) Uani 0.5 1 d . . P B 2
C21 C 0.31353(10) 0.51243(6) 0.4697(2) 0.0281(6) Uani 0.5 1 d G . P B 2
C22 C 0.23503(9) 0.47117(8) 0.46765(17) 0.0286(4) Uani 0.5 1 d G . P B 2
C23 C 0.19767(8) 0.39309(8) 0.4846(2) 0.0377(5) Uani 0.5 1 d G . P B 2
H23 H 0.144024 0.364890 0.483220 0.045 Uiso 0.5 1 calc R U P B 2
C24 C 0.23881(10) 0.35629(7) 0.5036(3) 0.0436(8) Uani 0.5 1 d G . P B 2
H24 H 0.213277 0.302925 0.515229 0.052 Uiso 0.5 1 calc R U P B 2
C25 C 0.31731(9) 0.39755(9) 0.5057(3) 0.0421(8) Uani 0.5 1 d G . P B 2
H25 H 0.345422 0.372394 0.518677 0.050 Uiso 0.5 1 calc R U P B 2
C26 C 0.35467(8) 0.47563(9) 0.48872(18) 0.0322(4) Uani 0.5 1 d G . P B 2
H26 H 0.408315 0.503829 0.490116 0.039 Uiso 0.5 1 calc R U P B 2
C27 C 0.19888(10) 0.51942(9) 0.45087(19) 0.0264(4) Uani 0.5 1 d . . P B 2
H27 H 0.166741 0.512805 0.543257 0.032 Uiso 0.5 1 calc R U P B 2
C28 C 0.15139(15) 0.50123(14) 0.3038(3) 0.0329(5) Uani 0.5 1 d . . P B 2
H28A H 0.182478 0.505385 0.214069 0.049 Uiso 0.5 1 calc R U P B 2
H28B H 0.132922 0.536967 0.292877 0.049 Uiso 0.5 1 calc R U P B 2
H28C H 0.108327 0.449677 0.310315 0.049 Uiso 0.5 1 calc R U P B 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
B1 N1 1.410(4) 3_565 ?
B1 N1 1.447(4) . ?
B1 C1 1.577(5) . ?
N1 C7 1.470(2) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 C7 1.506(2) . ?
C7 C8 1.528(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
B2 N2 1.413(4) 2_665 ?
B2 N2 1.445(3) . ?
B2 C21 1.569(5) . ?
N2 C27 1.473(2) . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C22 C23 1.3900 . ?
C22 C27 1.506(2) . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C26 1.3900 . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.529(3) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 B1 N1 119.4(4) 3_565 . ?
N1 B1 C1 135.3(4) 3_565 . ?
N1 B1 C1 105.3(2) . . ?
B1 N1 B1 120.5(4) 2_665 . ?
B1 N1 C7 127.2(3) 2_665 . ?
B1 N1 C7 112.1(2) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 B1 134.23(18) . . ?
C6 C1 B1 105.66(18) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 126.54(12) . . ?
C1 C6 C7 113.45(12) . . ?
N1 C7 C6 103.36(16) . . ?
N1 C7 C8 112.16(16) . . ?
C6 C7 C8 112.00(15) . . ?
N1 C7 H7 109.7 . . ?
C6 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 B2 N2 119.0(4) 2_665 . ?
N2 B2 C21 135.4(4) 2_665 . ?
N2 B2 C21 105.5(3) . . ?
B2 N2 B2 120.9(4) 3_565 . ?
B2 N2 C27 126.9(3) 3_565 . ?
B2 N2 C27 112.0(2) . . ?
C22 C21 C26 120.0 . . ?
C22 C21 B2 105.71(18) . . ?
C26 C21 B2 134.27(18) . . ?
C23 C22 C21 120.0 . . ?
C23 C22 C27 126.45(12) . . ?
C21 C22 C27 113.53(12) . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
N2 C27 C22 103.10(16) . . ?
N2 C27 C28 111.87(16) . . ?
C22 C27 C28 112.37(16) . . ?
N2 C27 H27 109.8 . . ?
C22 C27 H27 109.8 . . ?
C28 C27 H27 109.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
N1 B1 N1 B1 5.4(6) 3_565 . . 2_665 ?
C1 B1 N1 B1 -172.50(15) . . . 2_665 ?
N1 B1 N1 C7 -180.0(2) 3_565 . . . ?
C1 B1 N1 C7 2.2(3) . . . . ?
N1 B1 C1 C2 -1.1(5) 3_565 . . . ?
N1 B1 C1 C2 176.24(15) . . . . ?
N1 B1 C1 C6 -177.2(3) 3_565 . . . ?
N1 B1 C1 C6 0.1(2) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
B1 C1 C2 C3 -175.7(3) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 178.99(17) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
B1 C1 C6 C5 176.80(19) . . . . ?
C2 C1 C6 C7 -179.12(15) . . . . ?
B1 C1 C6 C7 -2.31(17) . . . . ?
B1 N1 C7 C6 170.8(2) 2_665 . . . ?
B1 N1 C7 C6 -3.4(2) . . . . ?
B1 N1 C7 C8 -68.3(3) 2_665 . . . ?
B1 N1 C7 C8 117.4(2) . . . . ?
C5 C6 C7 N1 -175.49(14) . . . . ?
C1 C6 C7 N1 3.56(15) . . . . ?
C5 C6 C7 C8 63.6(2) . . . . ?
C1 C6 C7 C8 -117.37(15) . . . . ?
N2 B2 N2 B2 -5.4(5) 2_665 . . 3_565 ?
C21 B2 N2 B2 172.12(15) . . . 3_565 ?
N2 B2 N2 C27 178.9(2) 2_665 . . . ?
C21 B2 N2 C27 -3.6(3) . . . . ?
N2 B2 C21 C22 179.0(3) 2_665 . . . ?
N2 B2 C21 C22 2.2(2) . . . . ?
N2 B2 C21 C26 1.0(5) 2_665 . . . ?
N2 B2 C21 C26 -175.83(15) . . . . ?
C26 C21 C22 C23 0.0 . . . . ?
B2 C21 C22 C23 -178.4(2) . . . . ?
C26 C21 C22 C27 178.29(15) . . . . ?
B2 C21 C22 C27 -0.07(17) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C27 C22 C23 C24 -178.05(17) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C21 0.0 . . . . ?
C22 C21 C26 C25 0.0 . . . . ?
B2 C21 C26 C25 177.8(3) . . . . ?
B2 N2 C27 C22 -171.9(2) 3_565 . . . ?
B2 N2 C27 C22 3.5(2) . . . . ?
B2 N2 C27 C28 67.1(3) 3_565 . . . ?
B2 N2 C27 C28 -117.5(2) . . . . ?
C23 C22 C27 N2 176.14(14) . . . . ?
C21 C22 C27 N2 -2.01(15) . . . . ?
C23 C22 C27 C28 -63.2(2) . . . . ?
C21 C22 C27 C28 118.60(15) . . . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.026


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 9:1 hexane:2-propyl alcohol mixture'
