# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_bn201r_0m
_database_code_depnum_ccdc_archive 'CCDC 1408898'
_audit_update_record             
;
2015-06-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H25 B N2'
_chemical_formula_sum            'C29 H25 B N2'
_chemical_formula_weight         412.32

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   17.3899(3)
_cell_length_b                   10.3122(2)
_cell_length_c                   26.5129(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.4870(10)
_cell_angle_gamma                90.00
_cell_volume                     4509.15(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.56

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63086
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7928
_reflns_number_gt                6507
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0471P)²+5.4376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7928
_refine_ls_number_parameters     581
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1548
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.37141(13) 0.2294(2) 1.07066(9) 0.0242(5) Uani 1 1 d . . .
N2 N 0.17495(13) 0.6692(2) 0.93252(9) 0.0297(6) Uani 1 1 d . . .
N3 N 0.63452(13) 0.3079(2) 0.83412(9) 0.0241(5) Uani 1 1 d . . .
N4 N 0.43304(14) 0.7357(2) 0.69340(10) 0.0343(6) Uani 1 1 d . . .
C2 C 0.32310(15) 0.3015(3) 1.09017(11) 0.0243(6) Uani 1 1 d . . .
C3 C 0.31732(17) 0.2791(3) 1.14144(11) 0.0294(6) Uani 1 1 d . . .
H3 H 0.2819 0.3299 1.1543 0.035 Uiso 1 1 calc R . .
C4 C 0.36274(18) 0.1846(3) 1.17197(12) 0.0337(7) Uani 1 1 d . . .
H4 H 0.3590 0.1687 1.2064 0.040 Uiso 1 1 calc R . .
C5 C 0.41576(16) 0.1092(3) 1.15308(11) 0.0293(7) Uani 1 1 d . . .
C6 C 0.41886(16) 0.1331(3) 1.10126(11) 0.0270(6) Uani 1 1 d . . .
C7 C 0.47056(16) 0.0571(3) 1.08169(12) 0.0318(7) Uani 1 1 d . . .
H7 H 0.4726 0.0706 1.0467 0.038 Uiso 1 1 calc R . .
C8 C 0.51789(18) -0.0364(3) 1.11360(13) 0.0389(8) Uani 1 1 d . . .
H8 H 0.5531 -0.0869 1.1004 0.047 Uiso 1 1 calc R . .
C9 C 0.51560(18) -0.0593(3) 1.16490(14) 0.0423(8) Uani 1 1 d . . .
H9 H 0.5490 -0.1245 1.1863 0.051 Uiso 1 1 calc R . .
C10 C 0.46563(18) 0.0118(3) 1.18422(13) 0.0386(8) Uani 1 1 d . . .
H10 H 0.4642 -0.0043 1.2192 0.046 Uiso 1 1 calc R . .
C11 C 0.28049(15) 0.3995(3) 1.05259(11) 0.0239(6) Uani 1 1 d . . .
C12 C 0.30020(16) 0.3916(3) 1.00524(11) 0.0240(6) Uani 1 1 d . . .
C13 C 0.32383(19) 0.1573(3) 0.96834(12) 0.0365(7) Uani 1 1 d . . .
H13A H 0.2735 0.1286 0.9741 0.055 Uiso 1 1 calc R . .
H13B H 0.3621 0.0848 0.9747 0.055 Uiso 1 1 calc R . .
H13C H 0.3119 0.1878 0.9316 0.055 Uiso 1 1 calc R . .
C14 C 0.44983(18) 0.3251(3) 1.00536(14) 0.0395(8) Uani 1 1 d . . .
H14A H 0.4412 0.3723 0.9719 0.059 Uiso 1 1 calc R . .
H14B H 0.4856 0.2509 1.0067 0.059 Uiso 1 1 calc R . .
H14C H 0.4749 0.3830 1.0354 0.059 Uiso 1 1 calc R . .
C15 C 0.26482(16) 0.4803(3) 0.96518(11) 0.0252(6) Uani 1 1 d . . .
H15 H 0.2766 0.4760 0.9326 0.030 Uiso 1 1 calc R . .
C16 C 0.21198(16) 0.5760(3) 0.97219(11) 0.0254(6) Uani 1 1 d . . .
C17 C 0.19395(16) 0.5812(3) 1.02012(11) 0.0256(6) Uani 1 1 d . . .
H17 H 0.1580 0.6459 1.0250 0.031 Uiso 1 1 calc R . .
C18 C 0.22788(15) 0.4934(3) 1.06013(11) 0.0250(6) Uani 1 1 d . . .
H18 H 0.2155 0.4970 1.0925 0.030 Uiso 1 1 calc R . .
C19 C 0.21159(16) 0.7219(3) 0.89674(11) 0.0257(6) Uani 1 1 d . . .
C20 C 0.29575(17) 0.7287(3) 0.90869(11) 0.0279(6) Uani 1 1 d . . .
H20 H 0.3302 0.6954 0.9415 0.033 Uiso 1 1 calc R . .
C21 C 0.32889(18) 0.7839(3) 0.87280(12) 0.0351(7) Uani 1 1 d . . .
H21 H 0.3862 0.7877 0.8813 0.042 Uiso 1 1 calc R . .
C22 C 0.2810(2) 0.8335(3) 0.82500(14) 0.0442(8) Uani 1 1 d . . .
H22 H 0.3046 0.8709 0.8007 0.053 Uiso 1 1 calc R . .
C23 C 0.1980(2) 0.8277(3) 0.81318(14) 0.0470(9) Uani 1 1 d . . .
H23 H 0.1641 0.8628 0.7806 0.056 Uiso 1 1 calc R . .
C24 C 0.16326(18) 0.7715(3) 0.84818(12) 0.0364(7) Uani 1 1 d . . .
H24 H 0.1059 0.7666 0.8390 0.044 Uiso 1 1 calc R . .
C25 C 0.09331(16) 0.7075(3) 0.92739(11) 0.0262(6) Uani 1 1 d . . .
C26 C 0.03419(17) 0.6133(3) 0.91803(12) 0.0338(7) Uani 1 1 d . . .
H26 H 0.0475 0.5248 0.9153 0.041 Uiso 1 1 calc R . .
C27 C -0.04471(18) 0.6491(3) 0.91260(13) 0.0399(8) Uani 1 1 d . . .
H27 H -0.0856 0.5845 0.9064 0.048 Uiso 1 1 calc R . .
C28 C -0.06441(19) 0.7758(3) 0.91610(13) 0.0419(8) Uani 1 1 d . . .
H28 H -0.1189 0.7990 0.9122 0.050 Uiso 1 1 calc R . .
C29 C -0.0059(2) 0.8704(3) 0.92525(12) 0.0423(8) Uani 1 1 d . . .
H29 H -0.0198 0.9588 0.9275 0.051 Uiso 1 1 calc R . .
C30 C 0.07362(19) 0.8358(3) 0.93119(12) 0.0368(7) Uani 1 1 d . . .
H30 H 0.1145 0.9006 0.9379 0.044 Uiso 1 1 calc R . .
C31 C 0.58533(16) 0.3784(3) 0.85358(11) 0.0246(6) Uani 1 1 d . . .
C32 C 0.57946(17) 0.3538(3) 0.90478(11) 0.0283(6) Uani 1 1 d . . .
H32 H 0.5435 0.4031 0.9176 0.034 Uiso 1 1 calc R . .
C33 C 0.62531(17) 0.2600(3) 0.93506(11) 0.0298(7) Uani 1 1 d . . .
H33 H 0.6210 0.2424 0.9692 0.036 Uiso 1 1 calc R . .
C34 C 0.67987(16) 0.1873(3) 0.91645(11) 0.0267(6) Uani 1 1 d . . .
C35 C 0.68288(16) 0.2121(3) 0.86462(11) 0.0247(6) Uani 1 1 d . . .
C36 C 0.73569(17) 0.1397(3) 0.84534(12) 0.0321(7) Uani 1 1 d . . .
H36 H 0.7368 0.1532 0.8101 0.038 Uiso 1 1 calc R . .
C37 C 0.78577(18) 0.0492(3) 0.87735(12) 0.0368(7) Uani 1 1 d . . .
H37 H 0.8220 0.0011 0.8642 0.044 Uiso 1 1 calc R . .
C38 C 0.78430(19) 0.0265(3) 0.92907(12) 0.0376(8) Uani 1 1 d . . .
H38 H 0.8199 -0.0356 0.9510 0.045 Uiso 1 1 calc R . .
C39 C 0.73197(18) 0.0934(3) 0.94790(12) 0.0344(7) Uani 1 1 d . . .
H39 H 0.7305 0.0766 0.9828 0.041 Uiso 1 1 calc R . .
C40 C 0.54199(16) 0.4756(3) 0.81589(11) 0.0251(6) Uani 1 1 d . . .
C41 C 0.56243(17) 0.4677(3) 0.76888(11) 0.0270(6) Uani 1 1 d . . .
C42 C 0.5872(2) 0.2370(3) 0.73177(12) 0.0449(9) Uani 1 1 d . . .
H42A H 0.5376 0.2063 0.7379 0.067 Uiso 1 1 calc R . .
H42B H 0.6262 0.1655 0.7375 0.067 Uiso 1 1 calc R . .
H42C H 0.5743 0.2686 0.6952 0.067 Uiso 1 1 calc R . .
C43 C 0.7134(2) 0.4062(3) 0.77006(14) 0.0444(9) Uani 1 1 d . . .
H43A H 0.7047 0.4603 0.7383 0.067 Uiso 1 1 calc R . .
H43B H 0.7479 0.3324 0.7684 0.067 Uiso 1 1 calc R . .
H43C H 0.7398 0.4578 0.8019 0.067 Uiso 1 1 calc R . .
C44 C 0.52550(17) 0.5535(3) 0.72807(11) 0.0297(7) Uani 1 1 d . . .
H44 H 0.5378 0.5488 0.6957 0.036 Uiso 1 1 calc R . .
C45 C 0.47062(16) 0.6465(3) 0.73386(11) 0.0281(6) Uani 1 1 d . . .
C46 C 0.45310(16) 0.6536(3) 0.78208(11) 0.0276(6) Uani 1 1 d . . .
H46 H 0.4171 0.7185 0.7867 0.033 Uiso 1 1 calc R . .
C47 C 0.48738(16) 0.5679(3) 0.82237(11) 0.0260(6) Uani 1 1 d . . .
H47 H 0.4741 0.5714 0.8544 0.031 Uiso 1 1 calc R . .
C48 C 0.45884(16) 0.7525(3) 0.64766(11) 0.0273(6) Uani 1 1 d . . .
C49 C 0.53924(17) 0.7780(3) 0.65306(12) 0.0329(7) Uani 1 1 d . . .
H49 H 0.5778 0.7861 0.6875 0.039 Uiso 1 1 calc R . .
C50 C 0.56343(18) 0.7917(3) 0.60877(13) 0.0355(7) Uani 1 1 d . . .
H50 H 0.6189 0.8081 0.6129 0.043 Uiso 1 1 calc R . .
C51 C 0.50835(19) 0.7820(3) 0.55851(13) 0.0392(8) Uani 1 1 d . . .
H51 H 0.5255 0.7907 0.5281 0.047 Uiso 1 1 calc R . .
C52 C 0.42805(19) 0.7593(3) 0.55289(13) 0.0404(8) Uani 1 1 d . . .
H52 H 0.3894 0.7547 0.5183 0.048 Uiso 1 1 calc R . .
C53 C 0.40317(17) 0.7434(3) 0.59711(12) 0.0326(7) Uani 1 1 d . . .
H53 H 0.3478 0.7262 0.5928 0.039 Uiso 1 1 calc R . .
C54 C 0.35434(17) 0.7851(3) 0.68952(11) 0.0318(7) Uani 1 1 d . . .
C55 C 0.3406(2) 0.9161(3) 0.68914(13) 0.0458(9) Uani 1 1 d . . .
H55 H 0.3835 0.9752 0.6916 0.055 Uiso 1 1 calc R . .
C56 C 0.2645(3) 0.9619(5) 0.68515(15) 0.0698(14) Uani 1 1 d . . .
H56 H 0.2553 1.0528 0.6850 0.084 Uiso 1 1 calc R . .
C57 C 0.2025(3) 0.8780(6) 0.68147(15) 0.0779(16) Uani 1 1 d . . .
H57 H 0.1501 0.9102 0.6786 0.093 Uiso 1 1 calc R . .
C58 C 0.2158(2) 0.7472(6) 0.68190(15) 0.0679(13) Uani 1 1 d . . .
H58 H 0.1724 0.6889 0.6792 0.082 Uiso 1 1 calc R . .
C59 C 0.29209(19) 0.6990(4) 0.68621(13) 0.0457(9) Uani 1 1 d . . .
H59 H 0.3014 0.6081 0.6869 0.055 Uiso 1 1 calc R . .
B1 B 0.36320(19) 0.2741(3) 1.00884(13) 0.0267(7) Uani 1 1 d . . .
B2 B 0.6261(2) 0.3533(3) 0.77264(13) 0.0301(8) 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 C2 1.342(3) . ?
N1 C6 1.379(3) . ?
N1 B1 1.664(4) . ?
N2 C19 1.409(3) . ?
N2 C16 1.419(3) . ?
N2 C25 1.438(3) . ?
N3 C31 1.344(3) . ?
N3 C35 1.380(3) . ?
N3 B2 1.657(4) . ?
N4 C45 1.407(3) . ?
N4 C48 1.431(4) . ?
N4 C54 1.433(4) . ?
C2 C3 1.413(4) . ?
C2 C11 1.447(4) . ?
C3 C4 1.350(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.414(4) . ?
C4 H4 0.9500 . ?
C5 C10 1.410(4) . ?
C5 C6 1.414(4) . ?
C6 C7 1.409(4) . ?
C7 C8 1.372(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.355(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C18 1.390(4) . ?
C11 C12 1.405(4) . ?
C12 C15 1.389(4) . ?
C12 B1 1.616(4) . ?
C13 B1 1.614(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 B1 1.626(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.401(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(4) . ?
C17 C18 1.377(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.392(4) . ?
C19 C20 1.397(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.377(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.378(4) . ?
C25 C30 1.378(4) . ?
C26 C27 1.383(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.362(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.374(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.416(4) . ?
C31 C40 1.447(4) . ?
C32 C33 1.345(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.415(4) . ?
C33 H33 0.9500 . ?
C34 C39 1.405(4) . ?
C34 C35 1.415(4) . ?
C35 C36 1.400(4) . ?
C36 C37 1.371(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.399(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.357(4) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C47 1.393(4) . ?
C40 C41 1.403(4) . ?
C41 C44 1.387(4) . ?
C41 B2 1.599(4) . ?
C42 B2 1.614(5) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 B2 1.634(5) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C45 1.396(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.407(4) . ?
C46 C47 1.369(4) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C49 1.385(4) . ?
C48 C53 1.385(4) . ?
C49 C50 1.375(4) . ?
C49 H49 0.9500 . ?
C50 C51 1.376(4) . ?
C50 H50 0.9500 . ?
C51 C52 1.376(4) . ?
C51 H51 0.9500 . ?
C52 C53 1.382(4) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 C55 1.371(4) . ?
C54 C59 1.382(4) . ?
C55 C56 1.376(5) . ?
C55 H55 0.9500 . ?
C56 C57 1.363(7) . ?
C56 H56 0.9500 . ?
C57 C58 1.368(7) . ?
C57 H57 0.9500 . ?
C58 C59 1.388(5) . ?
C58 H58 0.9500 . ?
C59 H59 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
C2 N1 C6 120.2(2) . . ?
C2 N1 B1 110.9(2) . . ?
C6 N1 B1 128.9(2) . . ?
C19 N2 C16 124.4(2) . . ?
C19 N2 C25 118.3(2) . . ?
C16 N2 C25 117.3(2) . . ?
C31 N3 C35 120.4(2) . . ?
C31 N3 B2 110.9(2) . . ?
C35 N3 B2 128.7(2) . . ?
C45 N4 C48 122.1(2) . . ?
C45 N4 C54 119.3(2) . . ?
C48 N4 C54 116.4(2) . . ?
N1 C2 C3 121.6(2) . . ?
N1 C2 C11 111.6(2) . . ?
C3 C2 C11 126.8(3) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C10 C5 C6 119.1(3) . . ?
C10 C5 C4 122.3(3) . . ?
C6 C5 C4 118.6(3) . . ?
N1 C6 C7 121.1(3) . . ?
N1 C6 C5 119.8(3) . . ?
C7 C6 C5 119.1(3) . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C18 C11 C12 121.8(2) . . ?
C18 C11 C2 127.2(2) . . ?
C12 C11 C2 111.0(2) . . ?
C15 C12 C11 118.1(2) . . ?
C15 C12 B1 131.8(2) . . ?
C11 C12 B1 110.1(2) . . ?
B1 C13 H13A 109.5 . . ?
B1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
B1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
B1 C14 H14A 109.5 . . ?
B1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
B1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C16 120.9(3) . . ?
C12 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.4(2) . . ?
C15 C16 N2 122.8(2) . . ?
C17 C16 N2 117.8(2) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C11 119.2(2) . . ?
C17 C18 H18 120.4 . . ?
C11 C18 H18 120.4 . . ?
C24 C19 C20 118.2(3) . . ?
C24 C19 N2 119.7(2) . . ?
C20 C19 N2 122.1(2) . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 118.6(3) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C22 C23 C24 120.9(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C26 C25 C30 120.1(3) . . ?
C26 C25 N2 118.8(2) . . ?
C30 C25 N2 121.1(3) . . ?
C25 C26 C27 119.3(3) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C28 C27 C26 120.8(3) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 120.3(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C30 119.5(3) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C25 C30 C29 120.0(3) . . ?
C25 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
N3 C31 C32 121.3(2) . . ?
N3 C31 C40 111.4(2) . . ?
C32 C31 C40 127.3(3) . . ?
C33 C32 C31 119.5(3) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 120.6(3) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C39 C34 C35 119.1(3) . . ?
C39 C34 C33 122.4(3) . . ?
C35 C34 C33 118.6(2) . . ?
N3 C35 C36 121.1(2) . . ?
N3 C35 C34 119.7(2) . . ?
C36 C35 C34 119.2(2) . . ?
C37 C36 C35 119.9(3) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 121.0(3) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 H37 119.5 . . ?
C39 C38 C37 119.9(3) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C34 120.9(3) . . ?
C38 C39 H39 119.6 . . ?
C34 C39 H39 119.6 . . ?
C47 C40 C41 121.6(2) . . ?
C47 C40 C31 127.9(2) . . ?
C41 C40 C31 110.5(2) . . ?
C44 C41 C40 118.1(3) . . ?
C44 C41 B2 131.2(3) . . ?
C40 C41 B2 110.7(2) . . ?
B2 C42 H42A 109.5 . . ?
B2 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
B2 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
B2 C43 H43A 109.5 . . ?
B2 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
B2 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 C45 121.1(3) . . ?
C41 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C44 C45 C46 119.2(2) . . ?
C44 C45 N4 122.3(3) . . ?
C46 C45 N4 118.5(2) . . ?
C47 C46 C45 120.6(3) . . ?
C47 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C46 C47 C40 119.4(3) . . ?
C46 C47 H47 120.3 . . ?
C40 C47 H47 120.3 . . ?
C49 C48 C53 119.1(3) . . ?
C49 C48 N4 120.9(3) . . ?
C53 C48 N4 120.1(2) . . ?
C50 C49 C48 120.2(3) . . ?
C50 C49 H49 119.9 . . ?
C48 C49 H49 119.9 . . ?
C49 C50 C51 120.8(3) . . ?
C49 C50 H50 119.6 . . ?
C51 C50 H50 119.6 . . ?
C52 C51 C50 119.2(3) . . ?
C52 C51 H51 120.4 . . ?
C50 C51 H51 120.4 . . ?
C51 C52 C53 120.5(3) . . ?
C51 C52 H52 119.7 . . ?
C53 C52 H52 119.7 . . ?
C52 C53 C48 120.1(3) . . ?
C52 C53 H53 119.9 . . ?
C48 C53 H53 119.9 . . ?
C55 C54 C59 120.1(3) . . ?
C55 C54 N4 120.8(3) . . ?
C59 C54 N4 119.2(3) . . ?
C54 C55 C56 120.0(4) . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C57 C56 C55 120.5(4) . . ?
C57 C56 H56 119.8 . . ?
C55 C56 H56 119.8 . . ?
C56 C57 C58 119.8(4) . . ?
C56 C57 H57 120.1 . . ?
C58 C57 H57 120.1 . . ?
C57 C58 C59 120.6(4) . . ?
C57 C58 H58 119.7 . . ?
C59 C58 H58 119.7 . . ?
C54 C59 C58 119.0(4) . . ?
C54 C59 H59 120.5 . . ?
C58 C59 H59 120.5 . . ?
C13 B1 C12 112.5(2) . . ?
C13 B1 C14 114.1(3) . . ?
C12 B1 C14 112.1(2) . . ?
C13 B1 N1 109.5(2) . . ?
C12 B1 N1 96.4(2) . . ?
C14 B1 N1 110.7(2) . . ?
C41 B2 C42 111.8(3) . . ?
C41 B2 C43 112.6(3) . . ?
C42 B2 C43 114.7(3) . . ?
C41 B2 N3 96.5(2) . . ?
C42 B2 N3 109.7(2) . . ?
C43 B2 N3 110.0(2) . . ?

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
C6 N1 C2 C3 -1.9(4) . . . . ?
B1 N1 C2 C3 177.8(2) . . . . ?
C6 N1 C2 C11 178.2(2) . . . . ?
B1 N1 C2 C11 -2.1(3) . . . . ?
N1 C2 C3 C4 1.4(4) . . . . ?
C11 C2 C3 C4 -178.7(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C10 178.4(3) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
C2 N1 C6 C7 -179.4(2) . . . . ?
B1 N1 C6 C7 0.9(4) . . . . ?
C2 N1 C6 C5 0.8(4) . . . . ?
B1 N1 C6 C5 -178.9(2) . . . . ?
C10 C5 C6 N1 -179.0(3) . . . . ?
C4 C5 C6 N1 0.8(4) . . . . ?
C10 C5 C6 C7 1.2(4) . . . . ?
C4 C5 C6 C7 -179.0(3) . . . . ?
N1 C6 C7 C8 178.9(3) . . . . ?
C5 C6 C7 C8 -1.3(4) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C8 C9 C10 C5 -0.2(5) . . . . ?
C6 C5 C10 C9 -0.5(4) . . . . ?
C4 C5 C10 C9 179.7(3) . . . . ?
N1 C2 C11 C18 -177.7(3) . . . . ?
C3 C2 C11 C18 2.4(4) . . . . ?
N1 C2 C11 C12 0.9(3) . . . . ?
C3 C2 C11 C12 -179.0(3) . . . . ?
C18 C11 C12 C15 -0.6(4) . . . . ?
C2 C11 C12 C15 -179.3(2) . . . . ?
C18 C11 C12 B1 179.3(2) . . . . ?
C2 C11 C12 B1 0.7(3) . . . . ?
C11 C12 C15 C16 0.9(4) . . . . ?
B1 C12 C15 C16 -179.0(3) . . . . ?
C12 C15 C16 C17 -0.7(4) . . . . ?
C12 C15 C16 N2 179.5(2) . . . . ?
C19 N2 C16 C15 -33.5(4) . . . . ?
C25 N2 C16 C15 143.7(3) . . . . ?
C19 N2 C16 C17 146.7(3) . . . . ?
C25 N2 C16 C17 -36.0(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
N2 C16 C17 C18 179.9(2) . . . . ?
C16 C17 C18 C11 0.2(4) . . . . ?
C12 C11 C18 C17 0.1(4) . . . . ?
C2 C11 C18 C17 178.5(3) . . . . ?
C16 N2 C19 C24 155.6(3) . . . . ?
C25 N2 C19 C24 -21.6(4) . . . . ?
C16 N2 C19 C20 -25.6(4) . . . . ?
C25 N2 C19 C20 157.2(3) . . . . ?
C24 C19 C20 C21 0.2(4) . . . . ?
N2 C19 C20 C21 -178.6(3) . . . . ?
C19 C20 C21 C22 0.2(5) . . . . ?
C20 C21 C22 C23 0.2(5) . . . . ?
C21 C22 C23 C24 -1.0(5) . . . . ?
C22 C23 C24 C19 1.4(5) . . . . ?
C20 C19 C24 C23 -1.0(5) . . . . ?
N2 C19 C24 C23 177.8(3) . . . . ?
C19 N2 C25 C26 120.6(3) . . . . ?
C16 N2 C25 C26 -56.8(4) . . . . ?
C19 N2 C25 C30 -58.8(4) . . . . ?
C16 N2 C25 C30 123.8(3) . . . . ?
C30 C25 C26 C27 -0.1(4) . . . . ?
N2 C25 C26 C27 -179.5(3) . . . . ?
C25 C26 C27 C28 0.4(5) . . . . ?
C26 C27 C28 C29 -0.2(5) . . . . ?
C27 C28 C29 C30 -0.3(5) . . . . ?
C26 C25 C30 C29 -0.4(4) . . . . ?
N2 C25 C30 C29 179.0(3) . . . . ?
C28 C29 C30 C25 0.6(5) . . . . ?
C35 N3 C31 C32 -2.3(4) . . . . ?
B2 N3 C31 C32 177.5(2) . . . . ?
C35 N3 C31 C40 178.3(2) . . . . ?
B2 N3 C31 C40 -2.0(3) . . . . ?
N3 C31 C32 C33 1.5(4) . . . . ?
C40 C31 C32 C33 -179.1(3) . . . . ?
C31 C32 C33 C34 0.9(4) . . . . ?
C32 C33 C34 C39 176.5(3) . . . . ?
C32 C33 C34 C35 -2.3(4) . . . . ?
C31 N3 C35 C36 -178.7(3) . . . . ?
B2 N3 C35 C36 1.7(4) . . . . ?
C31 N3 C35 C34 0.7(4) . . . . ?
B2 N3 C35 C34 -179.0(3) . . . . ?
C39 C34 C35 N3 -177.3(2) . . . . ?
C33 C34 C35 N3 1.6(4) . . . . ?
C39 C34 C35 C36 2.1(4) . . . . ?
C33 C34 C35 C36 -179.1(3) . . . . ?
N3 C35 C36 C37 177.0(3) . . . . ?
C34 C35 C36 C37 -2.3(4) . . . . ?
C35 C36 C37 C38 0.8(5) . . . . ?
C36 C37 C38 C39 0.9(5) . . . . ?
C37 C38 C39 C34 -1.1(5) . . . . ?
C35 C34 C39 C38 -0.4(4) . . . . ?
C33 C34 C39 C38 -179.2(3) . . . . ?
N3 C31 C40 C47 -178.4(3) . . . . ?
C32 C31 C40 C47 2.1(5) . . . . ?
N3 C31 C40 C41 1.0(3) . . . . ?
C32 C31 C40 C41 -178.4(3) . . . . ?
C47 C40 C41 C44 -1.2(4) . . . . ?
C31 C40 C41 C44 179.3(2) . . . . ?
C47 C40 C41 B2 180.0(3) . . . . ?
C31 C40 C41 B2 0.4(3) . . . . ?
C40 C41 C44 C45 1.1(4) . . . . ?
B2 C41 C44 C45 179.7(3) . . . . ?
C41 C44 C45 C46 0.4(4) . . . . ?
C41 C44 C45 N4 179.2(3) . . . . ?
C48 N4 C45 C44 -11.3(4) . . . . ?
C54 N4 C45 C44 151.2(3) . . . . ?
C48 N4 C45 C46 167.5(3) . . . . ?
C54 N4 C45 C46 -30.0(4) . . . . ?
C44 C45 C46 C47 -2.0(4) . . . . ?
N4 C45 C46 C47 179.2(3) . . . . ?
C45 C46 C47 C40 2.0(4) . . . . ?
C41 C40 C47 C46 -0.4(4) . . . . ?
C31 C40 C47 C46 179.1(3) . . . . ?
C45 N4 C48 C49 -53.1(4) . . . . ?
C54 N4 C48 C49 143.9(3) . . . . ?
C45 N4 C48 C53 126.9(3) . . . . ?
C54 N4 C48 C53 -36.0(4) . . . . ?
C53 C48 C49 C50 -1.2(4) . . . . ?
N4 C48 C49 C50 178.9(3) . . . . ?
C48 C49 C50 C51 0.8(5) . . . . ?
C49 C50 C51 C52 0.6(5) . . . . ?
C50 C51 C52 C53 -1.6(5) . . . . ?
C51 C52 C53 C48 1.2(5) . . . . ?
C49 C48 C53 C52 0.2(4) . . . . ?
N4 C48 C53 C52 -179.9(3) . . . . ?
C45 N4 C54 C55 125.7(3) . . . . ?
C48 N4 C54 C55 -70.9(4) . . . . ?
C45 N4 C54 C59 -54.2(4) . . . . ?
C48 N4 C54 C59 109.2(3) . . . . ?
C59 C54 C55 C56 -0.4(5) . . . . ?
N4 C54 C55 C56 179.7(3) . . . . ?
C54 C55 C56 C57 -0.1(6) . . . . ?
C55 C56 C57 C58 0.2(6) . . . . ?
C56 C57 C58 C59 0.2(6) . . . . ?
C55 C54 C59 C58 0.8(5) . . . . ?
N4 C54 C59 C58 -179.3(3) . . . . ?
C57 C58 C59 C54 -0.7(5) . . . . ?
C15 C12 B1 C13 -67.4(4) . . . . ?
C11 C12 B1 C13 112.6(3) . . . . ?
C15 C12 B1 C14 62.9(4) . . . . ?
C11 C12 B1 C14 -117.0(3) . . . . ?
C15 C12 B1 N1 178.4(3) . . . . ?
C11 C12 B1 N1 -1.6(3) . . . . ?
C2 N1 B1 C13 -114.5(3) . . . . ?
C6 N1 B1 C13 65.3(3) . . . . ?
C2 N1 B1 C12 2.2(3) . . . . ?
C6 N1 B1 C12 -178.1(2) . . . . ?
C2 N1 B1 C14 118.8(2) . . . . ?
C6 N1 B1 C14 -61.5(3) . . . . ?
C44 C41 B2 C42 -65.8(4) . . . . ?
C40 C41 B2 C42 112.9(3) . . . . ?
C44 C41 B2 C43 65.0(4) . . . . ?
C40 C41 B2 C43 -116.3(3) . . . . ?
C44 C41 B2 N3 179.9(3) . . . . ?
C40 C41 B2 N3 -1.4(3) . . . . ?
C31 N3 B2 C41 2.0(3) . . . . ?
C35 N3 B2 C41 -178.3(2) . . . . ?
C31 N3 B2 C42 -113.9(3) . . . . ?
C35 N3 B2 C42 65.7(4) . . . . ?
C31 N3 B2 C43 119.0(3) . . . . ?
C35 N3 B2 C43 -61.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.047
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pet Ether Ethyl Acetate MIxture'
####################################################################### 
# 
# 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_bn_301
_database_code_depnum_ccdc_archive 'CCDC 1408899'
_audit_update_record             
;
2015-06-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H20 B N'
_chemical_formula_sum            'C27 H20 B N'
_chemical_formula_weight         369.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   8.8980(4)
_cell_length_b                   7.0675(3)
_cell_length_c                   30.3620(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.000(3)
_cell_angle_gamma                90.00
_cell_volume                     1890.78(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3218
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.39

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13377
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3338
_reflns_number_gt                2420
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0404P)²+0.8044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0090(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.88069(17) 0.7582(2) 0.04594(5) 0.0370(4) Uani 1 1 d . . .
C2 C 1.0224(2) 0.7617(3) 0.06886(6) 0.0356(5) Uani 1 1 d . . .
C3 C 1.1491(2) 0.7488(3) 0.04583(7) 0.0423(5) Uani 1 1 d . . .
H3 H 1.2464 0.7465 0.0616 0.051 Uiso 1 1 calc R . .
C4 C 1.1301(2) 0.7399(3) 0.00108(7) 0.0446(5) Uani 1 1 d . . .
H4 H 1.2148 0.7321 -0.0137 0.053 Uiso 1 1 calc R . .
C5 C 0.9838(2) 0.7421(3) -0.02382(7) 0.0405(5) Uani 1 1 d . . .
C6 C 0.8583(2) 0.7520(3) 0.00003(6) 0.0374(5) Uani 1 1 d . . .
C7 C 0.7108(2) 0.7532(3) -0.02393(7) 0.0467(5) Uani 1 1 d . . .
H7 H 0.6269 0.7604 -0.0088 0.056 Uiso 1 1 calc R . .
C8 C 0.6909(3) 0.7437(3) -0.06931(7) 0.0524(6) Uani 1 1 d . . .
H8 H 0.5931 0.7448 -0.0848 0.063 Uiso 1 1 calc R . .
C9 C 0.8146(3) 0.7324(3) -0.09291(7) 0.0542(6) Uani 1 1 d . . .
H9 H 0.7989 0.7248 -0.1238 0.065 Uiso 1 1 calc R . .
C10 C 0.9583(3) 0.7324(3) -0.07060(7) 0.0491(6) Uani 1 1 d . . .
H10 H 1.0405 0.7259 -0.0864 0.059 Uiso 1 1 calc R . .
C11 C 1.0176(2) 0.7677(3) 0.11688(6) 0.0363(5) Uani 1 1 d . . .
C12 C 0.8658(2) 0.7497(3) 0.12452(7) 0.0386(5) Uani 1 1 d . . .
C13 C 0.6442(2) 0.5678(3) 0.07226(7) 0.0541(6) Uani 1 1 d . . .
H13A H 0.7074 0.4573 0.0739 0.081 Uiso 1 1 calc R . .
H13B H 0.5830 0.5731 0.0436 0.081 Uiso 1 1 calc R . .
H13C H 0.5795 0.5621 0.0950 0.081 Uiso 1 1 calc R . .
C14 C 0.6533(2) 0.9505(3) 0.07473(7) 0.0547(6) Uani 1 1 d . . .
H14A H 0.5900 0.9567 0.0978 0.082 Uiso 1 1 calc R . .
H14B H 0.5911 0.9541 0.0463 0.082 Uiso 1 1 calc R . .
H14C H 0.7216 1.0563 0.0774 0.082 Uiso 1 1 calc R . .
C15 C 0.8359(2) 0.7329(3) 0.16793(7) 0.0445(5) Uani 1 1 d . . .
H15 H 0.7359 0.7198 0.1731 0.053 Uiso 1 1 calc R . .
C16 C 0.9513(2) 0.7349(3) 0.20412(7) 0.0428(5) Uani 1 1 d . . .
C17 C 0.9211(3) 0.7128(3) 0.24925(8) 0.0522(6) Uani 1 1 d . . .
H17 H 0.8219 0.6923 0.2545 0.063 Uiso 1 1 calc R . .
C18 C 1.0320(3) 0.7210(3) 0.28377(8) 0.0600(7) Uani 1 1 d . . .
H18 H 1.0086 0.7021 0.3124 0.072 Uiso 1 1 calc R . .
C19 C 1.1852(3) 0.7581(3) 0.27773(7) 0.0526(6) Uani 1 1 d . . .
C20 C 1.3017(3) 0.7797(4) 0.31350(8) 0.0668(8) Uani 1 1 d . . .
H20 H 1.2806 0.7612 0.3423 0.080 Uiso 1 1 calc R . .
C21 C 1.4467(3) 0.8277(4) 0.30682(9) 0.0731(8) Uani 1 1 d . . .
H21 H 1.5215 0.8434 0.3311 0.088 Uiso 1 1 calc R . .
C22 C 1.4818(3) 0.8526(4) 0.26461(8) 0.0625(7) Uani 1 1 d . . .
H22 H 1.5800 0.8865 0.2606 0.075 Uiso 1 1 calc R . .
C23 C 1.3708(2) 0.8275(3) 0.22750(7) 0.0480(6) Uani 1 1 d . . .
C24 C 1.2206(3) 0.7814(3) 0.23381(7) 0.0430(5) Uani 1 1 d . . .
C25 C 1.1043(2) 0.7652(3) 0.19645(7) 0.0396(5) Uani 1 1 d . . .
C26 C 1.1393(2) 0.7856(3) 0.15230(7) 0.0379(5) Uani 1 1 d . . .
C27 C 1.2931(2) 0.8331(3) 0.14770(7) 0.0464(6) Uani 1 1 d . . .
H27 H 1.3191 0.8500 0.1193 0.056 Uiso 1 1 calc R . .
C28 C 1.4015(2) 0.8542(4) 0.18327(7) 0.0526(6) Uani 1 1 d . . .
H28 H 1.4993 0.8872 0.1786 0.063 Uiso 1 1 calc R . .
B1 B 0.7499(3) 0.7555(4) 0.07936(8) 0.0401(6) 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 C2 1.353(2) . ?
N1 C6 1.381(2) . ?
N1 B1 1.647(3) . ?
C2 C3 1.410(3) . ?
C2 C11 1.465(3) . ?
C3 C4 1.347(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.412(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.409(3) . ?
C5 C6 1.414(3) . ?
C6 C7 1.409(3) . ?
C7 C8 1.366(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.361(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.407(3) . ?
C11 C26 1.422(3) . ?
C12 C15 1.386(3) . ?
C12 B1 1.598(3) . ?
C13 B1 1.623(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 B1 1.620(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9300 . ?
C16 C25 1.429(3) . ?
C16 C17 1.441(3) . ?
C17 C18 1.337(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.425(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(3) . ?
C19 C24 1.422(3) . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.402(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.415(3) . ?
C23 C28 1.420(3) . ?
C24 C25 1.429(3) . ?
C25 C26 1.425(3) . ?
C26 C27 1.435(3) . ?
C27 C28 1.353(3) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
C2 N1 C6 120.86(16) . . ?
C2 N1 B1 111.77(16) . . ?
C6 N1 B1 127.34(16) . . ?
N1 C2 C3 119.73(18) . . ?
N1 C2 C11 111.00(16) . . ?
C3 C2 C11 129.15(18) . . ?
C4 C3 C2 120.44(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.09(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C10 C5 C6 119.39(19) . . ?
C10 C5 C4 123.13(19) . . ?
C6 C5 C4 117.47(18) . . ?
N1 C6 C7 120.92(18) . . ?
N1 C6 C5 120.33(18) . . ?
C7 C6 C5 118.74(19) . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 121.3(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C12 C11 C26 122.04(18) . . ?
C12 C11 C2 108.85(17) . . ?
C26 C11 C2 129.11(17) . . ?
C15 C12 C11 118.71(19) . . ?
C15 C12 B1 129.19(17) . . ?
C11 C12 B1 112.08(17) . . ?
B1 C13 H13A 109.5 . . ?
B1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
B1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
B1 C14 H14A 109.5 . . ?
B1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
B1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C16 122.03(18) . . ?
C12 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C25 119.11(18) . . ?
C15 C16 C17 122.3(2) . . ?
C25 C16 C17 118.6(2) . . ?
C18 C17 C16 121.7(2) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 121.5(2) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C24 118.5(2) . . ?
C20 C19 C18 122.5(2) . . ?
C24 C19 C18 118.9(2) . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 119.6(2) . . ?
C22 C23 C28 122.4(2) . . ?
C24 C23 C28 117.95(19) . . ?
C23 C24 C19 119.4(2) . . ?
C23 C24 C25 120.27(19) . . ?
C19 C24 C25 120.3(2) . . ?
C26 C25 C16 120.40(19) . . ?
C26 C25 C24 120.66(19) . . ?
C16 C25 C24 118.91(18) . . ?
C11 C26 C25 117.38(17) . . ?
C11 C26 C27 125.70(18) . . ?
C25 C26 C27 116.82(18) . . ?
C28 C27 C26 122.2(2) . . ?
C28 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
C27 C28 C23 122.1(2) . . ?
C27 C28 H28 119.0 . . ?
C23 C28 H28 119.0 . . ?
C12 B1 C14 111.56(19) . . ?
C12 B1 C13 112.73(18) . . ?
C14 B1 C13 113.14(18) . . ?
C12 B1 N1 95.85(14) . . ?
C14 B1 N1 110.38(17) . . ?
C13 B1 N1 111.95(18) . . ?

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
C6 N1 C2 C3 -3.4(3) . . . . ?
B1 N1 C2 C3 174.83(18) . . . . ?
C6 N1 C2 C11 -179.86(17) . . . . ?
B1 N1 C2 C11 -1.6(2) . . . . ?
N1 C2 C3 C4 2.4(3) . . . . ?
C11 C2 C3 C4 178.1(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C10 -179.8(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C2 N1 C6 C7 -178.36(19) . . . . ?
B1 N1 C6 C7 3.7(3) . . . . ?
C2 N1 C6 C5 2.4(3) . . . . ?
B1 N1 C6 C5 -175.56(19) . . . . ?
C10 C5 C6 N1 178.84(19) . . . . ?
C4 C5 C6 N1 -0.3(3) . . . . ?
C10 C5 C6 C7 -0.5(3) . . . . ?
C4 C5 C6 C7 -179.59(19) . . . . ?
N1 C6 C7 C8 -178.9(2) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C5 0.5(4) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C4 C5 C10 C9 179.1(2) . . . . ?
N1 C2 C11 C12 5.5(2) . . . . ?
C3 C2 C11 C12 -170.5(2) . . . . ?
N1 C2 C11 C26 -175.3(2) . . . . ?
C3 C2 C11 C26 8.7(4) . . . . ?
C26 C11 C12 C15 -5.6(3) . . . . ?
C2 C11 C12 C15 173.70(18) . . . . ?
C26 C11 C12 B1 173.51(19) . . . . ?
C2 C11 C12 B1 -7.2(2) . . . . ?
C11 C12 C15 C16 0.6(3) . . . . ?
B1 C12 C15 C16 -178.3(2) . . . . ?
C12 C15 C16 C25 3.4(3) . . . . ?
C12 C15 C16 C17 -178.4(2) . . . . ?
C15 C16 C17 C18 -177.8(2) . . . . ?
C25 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 2.0(4) . . . . ?
C17 C18 C19 C20 175.7(2) . . . . ?
C17 C18 C19 C24 -1.8(4) . . . . ?
C24 C19 C20 C21 1.8(4) . . . . ?
C18 C19 C20 C21 -175.7(3) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
C21 C22 C23 C24 1.8(4) . . . . ?
C21 C22 C23 C28 179.1(2) . . . . ?
C22 C23 C24 C19 -1.1(3) . . . . ?
C28 C23 C24 C19 -178.5(2) . . . . ?
C22 C23 C24 C25 176.7(2) . . . . ?
C28 C23 C24 C25 -0.7(3) . . . . ?
C20 C19 C24 C23 -0.7(3) . . . . ?
C18 C19 C24 C23 176.9(2) . . . . ?
C20 C19 C24 C25 -178.5(2) . . . . ?
C18 C19 C24 C25 -0.9(3) . . . . ?
C15 C16 C25 C26 -2.5(3) . . . . ?
C17 C16 C25 C26 179.28(19) . . . . ?
C15 C16 C25 C24 175.32(19) . . . . ?
C17 C16 C25 C24 -2.9(3) . . . . ?
C23 C24 C25 C26 3.2(3) . . . . ?
C19 C24 C25 C26 -179.1(2) . . . . ?
C23 C24 C25 C16 -174.6(2) . . . . ?
C19 C24 C25 C16 3.2(3) . . . . ?
C12 C11 C26 C25 6.3(3) . . . . ?
C2 C11 C26 C25 -172.8(2) . . . . ?
C12 C11 C26 C27 -169.9(2) . . . . ?
C2 C11 C26 C27 11.0(3) . . . . ?
C16 C25 C26 C11 -2.2(3) . . . . ?
C24 C25 C26 C11 -179.96(19) . . . . ?
C16 C25 C26 C27 174.33(19) . . . . ?
C24 C25 C26 C27 -3.4(3) . . . . ?
C11 C26 C27 C28 177.5(2) . . . . ?
C25 C26 C27 C28 1.3(3) . . . . ?
C26 C27 C28 C23 1.1(4) . . . . ?
C22 C23 C28 C27 -178.7(2) . . . . ?
C24 C23 C28 C27 -1.4(4) . . . . ?
C15 C12 B1 C14 70.0(3) . . . . ?
C11 C12 B1 C14 -109.0(2) . . . . ?
C15 C12 B1 C13 -58.6(3) . . . . ?
C11 C12 B1 C13 122.43(19) . . . . ?
C15 C12 B1 N1 -175.4(2) . . . . ?
C11 C12 B1 N1 5.7(2) . . . . ?
C2 N1 B1 C12 -2.3(2) . . . . ?
C6 N1 B1 C12 175.79(18) . . . . ?
C2 N1 B1 C14 113.33(19) . . . . ?
C6 N1 B1 C14 -68.6(3) . . . . ?
C2 N1 B1 C13 -119.67(19) . . . . ?
C6 N1 B1 C13 58.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pet Ether Dichloromethane MIxture'
####################################################################### 
# 
# 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_bn4cl_0m
_database_code_depnum_ccdc_archive 'CCDC 1408900'
_audit_update_record             
;
2015-06-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H23 B N2'
_chemical_formula_sum            'C29 H23 B N2'
_chemical_formula_weight         410.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3145(5)
_cell_length_b                   9.7778(6)
_cell_length_c                   12.5665(7)
_cell_angle_alpha                83.550(3)
_cell_angle_beta                 84.896(3)
_cell_angle_gamma                76.744(3)
_cell_volume                     1104.59(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5308
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      29.58

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15850
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3879
_reflns_number_gt                3046
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.4602P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3879
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36533(19) 0.72991(19) 0.42160(13) 0.0408(4) Uani 1 1 d . . .
N2 N 0.2460(2) 0.46637(19) 0.02961(14) 0.0432(5) Uani 1 1 d . . .
C2 C 0.4770(2) 0.6364(2) 0.37796(17) 0.0421(5) Uani 1 1 d . . .
C3 C 0.6198(3) 0.6059(3) 0.41684(19) 0.0520(6) Uani 1 1 d . . .
H3 H 0.6957 0.5395 0.3865 0.062 Uiso 1 1 calc R . .
C4 C 0.6448(3) 0.6743(3) 0.49854(19) 0.0553(6) Uani 1 1 d . . .
H4 H 0.7388 0.6550 0.5240 0.066 Uiso 1 1 calc R . .
C5 C 0.5307(3) 0.7742(3) 0.54559(17) 0.0494(6) Uani 1 1 d . . .
C6 C 0.3884(3) 0.7998(2) 0.50642(17) 0.0446(5) Uani 1 1 d . . .
C7 C 0.2719(3) 0.8976(3) 0.5535(2) 0.0568(7) Uani 1 1 d . . .
H7 H 0.1773 0.9137 0.5296 0.068 Uiso 1 1 calc R . .
C8 C 0.2985(3) 0.9686(3) 0.6344(2) 0.0679(8) Uani 1 1 d . . .
H8 H 0.2212 1.0337 0.6648 0.081 Uiso 1 1 calc R . .
C9 C 0.4391(4) 0.9459(3) 0.6726(2) 0.0704(8) Uani 1 1 d . . .
H9 H 0.4550 0.9959 0.7275 0.084 Uiso 1 1 calc R . .
C10 C 0.5518(3) 0.8510(3) 0.6294(2) 0.0625(7) Uani 1 1 d . . .
H10 H 0.6451 0.8359 0.6553 0.075 Uiso 1 1 calc R . .
C11 C 0.4314(2) 0.5781(2) 0.28837(16) 0.0409(5) Uani 1 1 d . . .
C12 C 0.2835(2) 0.6415(2) 0.27021(16) 0.0410(5) Uani 1 1 d . . .
C13 C 0.0821(3) 0.7014(3) 0.4355(2) 0.0577(7) Uani 1 1 d . . .
H13A H 0.0028 0.6959 0.3935 0.086 Uiso 1 1 calc R . .
H13B H 0.0460 0.7685 0.4872 0.086 Uiso 1 1 calc R . .
H13C H 0.1201 0.6103 0.4721 0.086 Uiso 1 1 calc R . .
C14 C 0.1675(3) 0.9114(3) 0.3029(2) 0.0656(7) Uani 1 1 d . . .
H14A H 0.0936 0.9179 0.2528 0.098 Uiso 1 1 calc R . .
H14B H 0.2530 0.9383 0.2660 0.098 Uiso 1 1 calc R . .
H14C H 0.1287 0.9734 0.3577 0.098 Uiso 1 1 calc R . .
C15 C 0.2236(2) 0.6019(2) 0.18387(17) 0.0427(5) Uani 1 1 d . . .
H15 H 0.1259 0.6421 0.1694 0.051 Uiso 1 1 calc R . .
C16 C 0.3075(2) 0.5036(2) 0.11941(16) 0.0410(5) Uani 1 1 d . . .
C17 C 0.4540(2) 0.4402(2) 0.14056(17) 0.0441(5) Uani 1 1 d . . .
H17 H 0.5093 0.3734 0.0972 0.053 Uiso 1 1 calc R . .
C18 C 0.5163(2) 0.4768(2) 0.22570(17) 0.0446(5) Uani 1 1 d . . .
H18 H 0.6133 0.4345 0.2409 0.054 Uiso 1 1 calc R . .
C19 C 0.1727(2) 0.5618(2) -0.05016(17) 0.0406(5) Uani 1 1 d . . .
C20 C 0.1420(3) 0.7075(3) -0.06065(19) 0.0495(6) Uani 1 1 d . . .
H20 H 0.1678 0.7573 -0.0092 0.059 Uiso 1 1 calc R . .
C21 C 0.0721(3) 0.7767(3) -0.1497(2) 0.0613(7) Uani 1 1 d . . .
H21 H 0.0486 0.8748 -0.1577 0.074 Uiso 1 1 calc R . .
C22 C 0.0354(3) 0.7024(3) -0.2289(2) 0.0617(7) Uani 1 1 d . . .
H22 H -0.0112 0.7517 -0.2886 0.074 Uiso 1 1 calc R . .
C23 C 0.0676(3) 0.5590(3) -0.21892(18) 0.0537(6) Uani 1 1 d . . .
H23 H 0.0429 0.5102 -0.2715 0.064 Uiso 1 1 calc R . .
C24 C 0.1381(2) 0.4851(3) -0.12887(17) 0.0430(5) Uani 1 1 d . . .
C25 C 0.1911(2) 0.3377(3) -0.09534(17) 0.0445(6) Uani 1 1 d . . .
C26 C 0.2568(2) 0.3295(2) 0.00247(17) 0.0433(5) Uani 1 1 d . . .
C27 C 0.3139(3) 0.2010(3) 0.0586(2) 0.0556(6) Uani 1 1 d . . .
H27 H 0.3558 0.1967 0.1237 0.067 Uiso 1 1 calc R . .
C28 C 0.3067(3) 0.0793(3) 0.0148(2) 0.0653(7) Uani 1 1 d . . .
H28 H 0.3443 -0.0082 0.0510 0.078 Uiso 1 1 calc R . .
C29 C 0.2442(3) 0.0856(3) -0.0822(2) 0.0671(8) Uani 1 1 d . . .
H29 H 0.2409 0.0024 -0.1103 0.081 Uiso 1 1 calc R . .
C30 C 0.1870(3) 0.2135(3) -0.1378(2) 0.0564(7) Uani 1 1 d . . .
H30 H 0.1459 0.2166 -0.2030 0.068 Uiso 1 1 calc R . .
B1 B 0.2132(3) 0.7512(3) 0.3571(2) 0.0444(6) 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 C2 1.339(3) . ?
N1 C6 1.386(3) . ?
N1 B1 1.656(3) . ?
N2 C26 1.398(3) . ?
N2 C19 1.400(3) . ?
N2 C16 1.427(3) . ?
C2 C3 1.413(3) . ?
C2 C11 1.454(3) . ?
C3 C4 1.350(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.412(3) . ?
C5 C6 1.413(3) . ?
C6 C7 1.407(3) . ?
C7 C8 1.363(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.350(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C18 1.390(3) . ?
C11 C12 1.402(3) . ?
C12 C15 1.393(3) . ?
C12 B1 1.608(3) . ?
C13 B1 1.628(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 B1 1.614(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(3) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.381(3) . ?
C19 C24 1.407(3) . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.404(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.359(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.402(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.439(3) . ?
C25 C30 1.390(3) . ?
C25 C26 1.407(3) . ?
C26 C27 1.385(3) . ?
C27 C28 1.383(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.386(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.378(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

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
C2 N1 C6 120.10(19) . . ?
C2 N1 B1 111.39(17) . . ?
C6 N1 B1 128.42(18) . . ?
C26 N2 C19 108.43(17) . . ?
C26 N2 C16 126.00(19) . . ?
C19 N2 C16 125.45(18) . . ?
N1 C2 C3 121.4(2) . . ?
N1 C2 C11 111.58(19) . . ?
C3 C2 C11 127.0(2) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C10 123.1(2) . . ?
C4 C5 C6 118.4(2) . . ?
C10 C5 C6 118.5(2) . . ?
N1 C6 C7 120.8(2) . . ?
N1 C6 C5 119.9(2) . . ?
C7 C6 C5 119.3(2) . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 121.3(3) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C18 C11 C12 122.5(2) . . ?
C18 C11 C2 127.6(2) . . ?
C12 C11 C2 109.87(19) . . ?
C15 C12 C11 117.4(2) . . ?
C15 C12 B1 131.4(2) . . ?
C11 C12 B1 111.16(18) . . ?
B1 C13 H13A 109.5 . . ?
B1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
B1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
B1 C14 H14A 109.5 . . ?
B1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
B1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C12 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C12 C15 H15 119.6 . . ?
C15 C16 C17 120.58(19) . . ?
C15 C16 N2 120.29(19) . . ?
C17 C16 N2 119.13(19) . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C11 118.7(2) . . ?
C17 C18 H18 120.7 . . ?
C11 C18 H18 120.7 . . ?
C20 C19 N2 129.6(2) . . ?
C20 C19 C24 121.7(2) . . ?
N2 C19 C24 108.62(19) . . ?
C21 C20 C19 117.8(2) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C22 121.5(3) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.6(2) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C19 118.9(2) . . ?
C23 C24 C25 133.9(2) . . ?
C19 C24 C25 107.11(19) . . ?
C30 C25 C26 118.9(2) . . ?
C30 C25 C24 133.8(2) . . ?
C26 C25 C24 107.22(19) . . ?
C27 C26 N2 129.6(2) . . ?
C27 C26 C25 121.7(2) . . ?
N2 C26 C25 108.6(2) . . ?
C28 C27 C26 118.0(2) . . ?
C28 C27 H27 121.0 . . ?
C26 C27 H27 121.0 . . ?
C27 C28 C29 121.0(3) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 120.9(2) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C25 119.4(2) . . ?
C29 C30 H30 120.3 . . ?
C25 C30 H30 120.3 . . ?
C12 B1 C14 112.30(19) . . ?
C12 B1 C13 112.7(2) . . ?
C14 B1 C13 113.7(2) . . ?
C12 B1 N1 95.95(17) . . ?
C14 B1 N1 109.88(19) . . ?
C13 B1 N1 110.91(18) . . ?

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
C6 N1 C2 C3 0.3(3) . . . . ?
B1 N1 C2 C3 177.2(2) . . . . ?
C6 N1 C2 C11 -178.28(18) . . . . ?
B1 N1 C2 C11 -1.4(2) . . . . ?
N1 C2 C3 C4 -1.2(4) . . . . ?
C11 C2 C3 C4 177.2(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C10 -178.4(2) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C2 N1 C6 C7 -179.6(2) . . . . ?
B1 N1 C6 C7 4.1(3) . . . . ?
C2 N1 C6 C5 1.2(3) . . . . ?
B1 N1 C6 C5 -175.1(2) . . . . ?
C4 C5 C6 N1 -1.8(3) . . . . ?
C10 C5 C6 N1 177.6(2) . . . . ?
C4 C5 C6 C7 178.9(2) . . . . ?
C10 C5 C6 C7 -1.6(3) . . . . ?
N1 C6 C7 C8 -177.7(2) . . . . ?
C5 C6 C7 C8 1.6(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C5 0.3(4) . . . . ?
C4 C5 C10 C9 -179.9(3) . . . . ?
C6 C5 C10 C9 0.7(4) . . . . ?
N1 C2 C11 C18 -178.6(2) . . . . ?
C3 C2 C11 C18 2.9(4) . . . . ?
N1 C2 C11 C12 2.5(3) . . . . ?
C3 C2 C11 C12 -176.1(2) . . . . ?
C18 C11 C12 C15 -1.7(3) . . . . ?
C2 C11 C12 C15 177.37(19) . . . . ?
C18 C11 C12 B1 178.5(2) . . . . ?
C2 C11 C12 B1 -2.4(3) . . . . ?
C11 C12 C15 C16 0.2(3) . . . . ?
B1 C12 C15 C16 180.0(2) . . . . ?
C12 C15 C16 C17 0.9(3) . . . . ?
C12 C15 C16 N2 -178.48(19) . . . . ?
C26 N2 C16 C15 -133.9(2) . . . . ?
C19 N2 C16 C15 50.6(3) . . . . ?
C26 N2 C16 C17 46.7(3) . . . . ?
C19 N2 C16 C17 -128.8(2) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
N2 C16 C17 C18 178.73(19) . . . . ?
C16 C17 C18 C11 -0.7(3) . . . . ?
C12 C11 C18 C17 1.9(3) . . . . ?
C2 C11 C18 C17 -176.9(2) . . . . ?
C26 N2 C19 C20 -177.0(2) . . . . ?
C16 N2 C19 C20 -0.8(3) . . . . ?
C26 N2 C19 C24 -0.6(2) . . . . ?
C16 N2 C19 C24 175.65(18) . . . . ?
N2 C19 C20 C21 177.8(2) . . . . ?
C24 C19 C20 C21 1.8(3) . . . . ?
C19 C20 C21 C22 -1.3(4) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C19 0.6(3) . . . . ?
C22 C23 C24 C25 -177.7(2) . . . . ?
C20 C19 C24 C23 -1.5(3) . . . . ?
N2 C19 C24 C23 -178.25(18) . . . . ?
C20 C19 C24 C25 177.23(19) . . . . ?
N2 C19 C24 C25 0.5(2) . . . . ?
C23 C24 C25 C30 -3.0(4) . . . . ?
C19 C24 C25 C30 178.6(2) . . . . ?
C23 C24 C25 C26 178.2(2) . . . . ?
C19 C24 C25 C26 -0.2(2) . . . . ?
C19 N2 C26 C27 -176.8(2) . . . . ?
C16 N2 C26 C27 7.0(4) . . . . ?
C19 N2 C26 C25 0.4(2) . . . . ?
C16 N2 C26 C25 -175.77(19) . . . . ?
C30 C25 C26 C27 -1.6(3) . . . . ?
C24 C25 C26 C27 177.4(2) . . . . ?
C30 C25 C26 N2 -179.11(19) . . . . ?
C24 C25 C26 N2 -0.1(2) . . . . ?
N2 C26 C27 C28 177.9(2) . . . . ?
C25 C26 C27 C28 0.9(3) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C28 C29 C30 C25 -0.4(4) . . . . ?
C26 C25 C30 C29 1.3(3) . . . . ?
C24 C25 C30 C29 -177.3(2) . . . . ?
C15 C12 B1 C14 -63.9(3) . . . . ?
C11 C12 B1 C14 115.8(2) . . . . ?
C15 C12 B1 C13 66.1(3) . . . . ?
C11 C12 B1 C13 -114.2(2) . . . . ?
C15 C12 B1 N1 -178.3(2) . . . . ?
C11 C12 B1 N1 1.5(2) . . . . ?
C2 N1 B1 C12 0.0(2) . . . . ?
C6 N1 B1 C12 176.53(19) . . . . ?
C2 N1 B1 C14 -116.3(2) . . . . ?
C6 N1 B1 C14 60.2(3) . . . . ?
C2 N1 B1 C13 117.1(2) . . . . ?
C6 N1 B1 C13 -66.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pet Ether Ethyl Acetate MIxture'
####################################################################### 
# 
# 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_bn_501_0m
_database_code_depnum_ccdc_archive 'CCDC 1408901'
_audit_update_record             
;
2015-06-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 B N'
_chemical_formula_sum            'C25 H20 B N'
_chemical_formula_weight         345.23

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   13.9351(7)
_cell_length_b                   9.0239(5)
_cell_length_c                   14.1194(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.128(3)
_cell_angle_gamma                90.00
_cell_volume                     1774.28(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9474
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      29.74

_exptl_crystal_description       PLATE
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22665
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3108
_reflns_number_gt                2911
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0891P)²+32.5990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3108
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.1623
_refine_ls_wR_factor_ref         0.4295
_refine_ls_wR_factor_gt          0.4284
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5035(5) 0.9046(8) 0.1676(5) 0.0202(16) Uani 1 1 d . . .
B1 B 0.5681(7) 0.8026(11) 0.2401(7) 0.025(2) Uani 1 1 d . . .
C1 C 0.4219(6) 0.8352(9) 0.1396(6) 0.0208(18) Uani 1 1 d . . .
C2 C 0.3494(6) 0.9110(9) 0.0872(6) 0.0240(19) Uani 1 1 d . . .
H2 H 0.2905 0.8632 0.0705 0.029 Uiso 1 1 calc R . .
C3 C 0.3651(6) 1.0537(10) 0.0609(6) 0.0237(19) Uani 1 1 d . . .
H3 H 0.3168 1.1050 0.0247 0.028 Uiso 1 1 calc R . .
C4 C 0.4509(6) 1.1264(9) 0.0861(6) 0.0223(19) Uani 1 1 d . . .
C5 C 0.5209(6) 1.0497(10) 0.1414(6) 0.0239(19) Uani 1 1 d . . .
C6 C 0.6083(7) 1.1221(10) 0.1691(7) 0.030(2) Uani 1 1 d . . .
H6 H 0.6566 1.0706 0.2052 0.036 Uiso 1 1 calc R . .
C7 C 0.6218(7) 1.2654(10) 0.1436(7) 0.031(2) Uani 1 1 d . . .
H7 H 0.6795 1.3140 0.1637 0.037 Uiso 1 1 calc R . .
C8 C 0.5528(7) 1.3444(10) 0.0881(6) 0.028(2) Uani 1 1 d . . .
H8 H 0.5646 1.4440 0.0701 0.034 Uiso 1 1 calc R . .
C9 C 0.4695(7) 1.2764(10) 0.0607(6) 0.027(2) Uani 1 1 d . . .
H9 H 0.4227 1.3297 0.0239 0.033 Uiso 1 1 calc R . .
C10 C 0.4199(6) 0.6855(9) 0.1790(6) 0.0223(19) Uani 1 1 d . . .
C11 C 0.4957(6) 0.6634(9) 0.2417(6) 0.0213(18) Uani 1 1 d . . .
C12 C 0.5827(7) 0.8885(10) 0.3397(7) 0.029(2) Uani 1 1 d . . .
H12A H 0.5198 0.9139 0.3641 0.043 Uiso 1 1 calc R . .
H12B H 0.6197 0.9794 0.3302 0.043 Uiso 1 1 calc R . .
H12C H 0.6175 0.8245 0.3853 0.043 Uiso 1 1 calc R . .
C13 C 0.6690(6) 0.7549(11) 0.1896(6) 0.028(2) Uani 1 1 d . . .
H13A H 0.7012 0.6768 0.2271 0.042 Uiso 1 1 calc R . .
H13B H 0.7113 0.8414 0.1865 0.042 Uiso 1 1 calc R . .
H13C H 0.6543 0.7182 0.1254 0.042 Uiso 1 1 calc R . .
C14 C 0.5025(6) 0.5329(10) 0.2978(6) 0.0251(19) Uani 1 1 d . . .
C15 C 0.5810(7) 0.5077(11) 0.3625(7) 0.033(2) Uani 1 1 d . . .
H15 H 0.6324 0.5769 0.3652 0.039 Uiso 1 1 calc R . .
C16 C 0.5852(8) 0.3871(11) 0.4213(7) 0.034(2) Uani 1 1 d . . .
H16 H 0.6386 0.3733 0.4641 0.040 Uiso 1 1 calc R . .
C17 C 0.5095(8) 0.2837(13) 0.4177(7) 0.041(3) Uani 1 1 d . . .
H17 H 0.5116 0.2000 0.4585 0.049 Uiso 1 1 calc R . .
C18 C 0.4323(7) 0.3038(11) 0.3549(7) 0.033(2) Uani 1 1 d . . .
H18 H 0.3812 0.2340 0.3537 0.040 Uiso 1 1 calc R . .
C19 C 0.4276(7) 0.4252(10) 0.2929(6) 0.026(2) Uani 1 1 d . . .
C20 C 0.3495(6) 0.4451(9) 0.2216(6) 0.0227(19) Uani 1 1 d . . .
C21 C 0.3465(6) 0.5693(9) 0.1604(6) 0.0209(18) Uani 1 1 d . . .
C22 C 0.2794(6) 0.5701(9) 0.0849(6) 0.0219(18) Uani 1 1 d . . .
H22 H 0.2800 0.6500 0.0411 0.026 Uiso 1 1 calc R . .
C23 C 0.2129(7) 0.4603(11) 0.0714(7) 0.030(2) Uani 1 1 d . . .
H23 H 0.1684 0.4643 0.0188 0.036 Uiso 1 1 calc R . .
C24 C 0.2104(6) 0.3417(10) 0.1353(6) 0.027(2) Uani 1 1 d . . .
H24 H 0.1622 0.2676 0.1290 0.032 Uiso 1 1 calc R . .
C25 C 0.2791(7) 0.3352(10) 0.2071(7) 0.030(2) Uani 1 1 d . . .
H25 H 0.2791 0.2527 0.2489 0.036 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.344(11) . ?
N1 C5 1.385(11) . ?
N1 B1 1.624(11) . ?
B1 C11 1.611(12) . ?
B1 C12 1.612(14) . ?
B1 C13 1.657(14) . ?
C1 C2 1.407(12) . ?
C1 C10 1.462(12) . ?
C2 C3 1.361(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(12) . ?
C4 C9 1.427(12) . ?
C5 C6 1.424(13) . ?
C6 C7 1.358(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.410(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.356(13) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.368(12) . ?
C10 C21 1.481(12) . ?
C11 C14 1.420(12) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.417(13) . ?
C14 C19 1.425(13) . ?
C15 C16 1.368(14) . ?
C15 H15 0.9500 . ?
C16 C17 1.407(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.403(13) . ?
C18 H18 0.9500 . ?
C19 C20 1.466(13) . ?
C20 C25 1.405(13) . ?
C20 C21 1.415(12) . ?
C21 C22 1.392(12) . ?
C22 C23 1.365(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.401(14) . ?
C23 H23 0.9500 . ?
C24 C25 1.369(14) . ?
C24 H24 0.9500 . ?
C25 H25 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
C1 N1 C5 121.1(7) . . ?
C1 N1 B1 111.4(7) . . ?
C5 N1 B1 127.3(7) . . ?
C11 B1 C12 114.9(7) . . ?
C11 B1 N1 96.8(7) . . ?
C12 B1 N1 109.0(7) . . ?
C11 B1 C13 110.2(8) . . ?
C12 B1 C13 114.7(8) . . ?
N1 B1 C13 109.6(7) . . ?
N1 C1 C2 120.7(8) . . ?
N1 C1 C10 110.3(7) . . ?
C2 C1 C10 128.7(8) . . ?
C3 C2 C1 119.0(8) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.3(8) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.6(8) . . ?
C3 C4 C9 122.9(8) . . ?
C5 C4 C9 118.5(8) . . ?
N1 C5 C4 119.2(8) . . ?
N1 C5 C6 121.1(8) . . ?
C4 C5 C6 119.7(8) . . ?
C7 C6 C5 119.3(9) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 122.0(9) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 119.2(9) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C4 121.3(9) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C11 C10 C1 110.8(8) . . ?
C11 C10 C21 121.6(8) . . ?
C1 C10 C21 127.6(8) . . ?
C10 C11 C14 121.0(8) . . ?
C10 C11 B1 110.3(7) . . ?
C14 C11 B1 128.7(8) . . ?
B1 C12 H12A 109.5 . . ?
B1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
B1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
B1 C13 H13A 109.5 . . ?
B1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
B1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 121.7(8) . . ?
C15 C14 C19 117.9(8) . . ?
C11 C14 C19 120.3(8) . . ?
C16 C15 C14 122.2(9) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 119.4(9) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.1(9) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 121.3(10) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C14 119.1(9) . . ?
C18 C19 C20 122.7(9) . . ?
C14 C19 C20 118.2(8) . . ?
C25 C20 C21 117.7(8) . . ?
C25 C20 C19 120.7(8) . . ?
C21 C20 C19 121.4(8) . . ?
C22 C21 C20 118.4(8) . . ?
C22 C21 C10 124.9(8) . . ?
C20 C21 C10 116.6(8) . . ?
C23 C22 C21 122.4(8) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C22 C23 C24 119.8(9) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 118.5(8) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 C20 122.9(8) . . ?
C24 C25 H25 118.6 . . ?
C20 C25 H25 118.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 B1 C11 -0.6(9) . . . . ?
C5 N1 B1 C11 173.8(8) . . . . ?
C1 N1 B1 C12 -120.0(8) . . . . ?
C5 N1 B1 C12 54.5(11) . . . . ?
C1 N1 B1 C13 113.7(8) . . . . ?
C5 N1 B1 C13 -71.9(11) . . . . ?
C5 N1 C1 C2 -3.7(12) . . . . ?
B1 N1 C1 C2 171.2(8) . . . . ?
C5 N1 C1 C10 -178.3(7) . . . . ?
B1 N1 C1 C10 -3.4(9) . . . . ?
N1 C1 C2 C3 3.4(13) . . . . ?
C10 C1 C2 C3 177.0(8) . . . . ?
C1 C2 C3 C4 -1.0(13) . . . . ?
C2 C3 C4 C5 -1.2(13) . . . . ?
C2 C3 C4 C9 -179.3(8) . . . . ?
C1 N1 C5 C4 1.4(12) . . . . ?
B1 N1 C5 C4 -172.6(8) . . . . ?
C1 N1 C5 C6 -178.5(8) . . . . ?
B1 N1 C5 C6 7.5(13) . . . . ?
C3 C4 C5 N1 1.0(12) . . . . ?
C9 C4 C5 N1 179.2(8) . . . . ?
C3 C4 C5 C6 -179.1(8) . . . . ?
C9 C4 C5 C6 -0.8(13) . . . . ?
N1 C5 C6 C7 -178.7(9) . . . . ?
C4 C5 C6 C7 1.4(14) . . . . ?
C5 C6 C7 C8 -1.6(15) . . . . ?
C6 C7 C8 C9 1.3(15) . . . . ?
C7 C8 C9 C4 -0.7(14) . . . . ?
C3 C4 C9 C8 178.6(9) . . . . ?
C5 C4 C9 C8 0.5(13) . . . . ?
N1 C1 C10 C11 6.9(10) . . . . ?
C2 C1 C10 C11 -167.2(9) . . . . ?
N1 C1 C10 C21 -175.5(8) . . . . ?
C2 C1 C10 C21 10.4(14) . . . . ?
C1 C10 C11 C14 172.2(7) . . . . ?
C21 C10 C11 C14 -5.6(12) . . . . ?
C1 C10 C11 B1 -7.3(10) . . . . ?
C21 C10 C11 B1 175.0(7) . . . . ?
C12 B1 C11 C10 119.5(8) . . . . ?
N1 B1 C11 C10 4.8(9) . . . . ?
C13 B1 C11 C10 -109.0(8) . . . . ?
C12 B1 C11 C14 -60.0(12) . . . . ?
N1 B1 C11 C14 -174.6(8) . . . . ?
C13 B1 C11 C14 71.5(11) . . . . ?
C10 C11 C14 C15 179.4(8) . . . . ?
B1 C11 C14 C15 -1.2(14) . . . . ?
C10 C11 C14 C19 -3.0(12) . . . . ?
B1 C11 C14 C19 176.3(8) . . . . ?
C11 C14 C15 C16 175.6(9) . . . . ?
C19 C14 C15 C16 -1.9(14) . . . . ?
C14 C15 C16 C17 0.2(15) . . . . ?
C15 C16 C17 C18 0.4(16) . . . . ?
C16 C17 C18 C19 0.8(16) . . . . ?
C17 C18 C19 C14 -2.6(14) . . . . ?
C17 C18 C19 C20 176.3(9) . . . . ?
C15 C14 C19 C18 3.1(12) . . . . ?
C11 C14 C19 C18 -174.5(8) . . . . ?
C15 C14 C19 C20 -175.9(8) . . . . ?
C11 C14 C19 C20 6.5(12) . . . . ?
C18 C19 C20 C25 -5.4(13) . . . . ?
C14 C19 C20 C25 173.5(8) . . . . ?
C18 C19 C20 C21 179.6(8) . . . . ?
C14 C19 C20 C21 -1.5(12) . . . . ?
C25 C20 C21 C22 -5.2(11) . . . . ?
C19 C20 C21 C22 170.0(8) . . . . ?
C25 C20 C21 C10 178.3(7) . . . . ?
C19 C20 C21 C10 -6.5(11) . . . . ?
C11 C10 C21 C22 -166.0(8) . . . . ?
C1 C10 C21 C22 16.6(13) . . . . ?
C11 C10 C21 C20 10.2(11) . . . . ?
C1 C10 C21 C20 -167.2(8) . . . . ?
C20 C21 C22 C23 4.2(12) . . . . ?
C10 C21 C22 C23 -179.6(8) . . . . ?
C21 C22 C23 C24 0.3(13) . . . . ?
C22 C23 C24 C25 -3.7(13) . . . . ?
C23 C24 C25 C20 2.6(13) . . . . ?
C21 C20 C25 C24 1.9(13) . . . . ?
C19 C20 C25 C24 -173.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.146
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pet Ether Ethyl Acetate MIxture'
####################################################################### 
# 
# 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_bn_602_0m
_database_code_depnum_ccdc_archive 'CCDC 1408902'
_audit_update_record             
;
2015-06-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 B N2'
_chemical_formula_sum            'C21 H25 B N2'
_chemical_formula_weight         316.24

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9636(2)
_cell_length_b                   8.8054(2)
_cell_length_c                   14.8492(5)
_cell_angle_alpha                106.476(2)
_cell_angle_beta                 90.570(2)
_cell_angle_gamma                116.512(2)
_cell_volume                     882.12(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6662
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      33.66

_exptl_crystal_description       PLATE
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12311
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3115
_reflns_number_gt                2747
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0448P)²+0.3717P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3115
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.11592(16) 0.16192(14) 0.29181(8) 0.0234(3) Uani 1 1 d . . .
N2 N 0.52163(19) 0.24100(17) -0.05091(9) 0.0342(3) Uani 1 1 d . . .
B1 B 0.3000(2) 0.3335(2) 0.27638(11) 0.0243(3) Uani 1 1 d . . .
C1 C 0.05535(19) 0.01526(18) 0.21398(10) 0.0249(3) Uani 1 1 d . . .
C2 C -0.0963(2) -0.15065(19) 0.21265(11) 0.0308(3) Uani 1 1 d . . .
H2 H -0.1345 -0.2541 0.1584 0.037 Uiso 1 1 calc R . .
C3 C -0.1867(2) -0.16133(19) 0.28887(11) 0.0327(4) Uani 1 1 d . . .
H3 H -0.2887 -0.2727 0.2879 0.039 Uiso 1 1 calc R . .
C4 C -0.1311(2) -0.00851(19) 0.37017(11) 0.0288(3) Uani 1 1 d . . .
C5 C 0.0256(2) 0.15433(19) 0.37060(10) 0.0255(3) Uani 1 1 d . . .
C6 C 0.0863(2) 0.3065(2) 0.45196(10) 0.0309(3) Uani 1 1 d . . .
H6 H 0.1922 0.4161 0.4537 0.037 Uiso 1 1 calc R . .
C7 C -0.0075(2) 0.2965(2) 0.52884(11) 0.0344(4) Uani 1 1 d . . .
H7 H 0.0344 0.4000 0.5834 0.041 Uiso 1 1 calc R . .
C8 C -0.1635(2) 0.1371(2) 0.52826(12) 0.0369(4) Uani 1 1 d . . .
H8 H -0.2274 0.1328 0.5819 0.044 Uiso 1 1 calc R . .
C9 C -0.2238(2) -0.0124(2) 0.45062(12) 0.0351(4) Uani 1 1 d . . .
H9 H -0.3297 -0.1207 0.4506 0.042 Uiso 1 1 calc R . .
C10 C 0.16353(19) 0.05306(18) 0.13886(10) 0.0244(3) Uani 1 1 d . . .
C11 C 0.30748(19) 0.23179(18) 0.16875(10) 0.0235(3) Uani 1 1 d . . .
C12 C 0.4871(2) 0.39288(18) 0.35041(10) 0.0278(3) Uani 1 1 d . . .
H12A H 0.6001 0.4741 0.3292 0.033 Uiso 1 1 calc R . .
H12B H 0.4773 0.4627 0.4135 0.033 Uiso 1 1 calc R . .
C13 C 0.5216(2) 0.2428(2) 0.36267(12) 0.0392(4) Uani 1 1 d . . .
H13A H 0.4144 0.1645 0.3872 0.059 Uiso 1 1 calc R . .
H13B H 0.6388 0.2943 0.4076 0.059 Uiso 1 1 calc R . .
H13C H 0.5337 0.1729 0.3011 0.059 Uiso 1 1 calc R . .
C14 C 0.2512(2) 0.49717(18) 0.28257(10) 0.0269(3) Uani 1 1 d . . .
H14A H 0.2581 0.5600 0.3504 0.032 Uiso 1 1 calc R . .
H14B H 0.3512 0.5838 0.2574 0.032 Uiso 1 1 calc R . .
C15 C 0.0578(2) 0.4437(2) 0.22926(11) 0.0339(4) Uani 1 1 d . . .
H15A H 0.0457 0.3755 0.1626 0.051 Uiso 1 1 calc R . .
H15B H 0.0472 0.5518 0.2327 0.051 Uiso 1 1 calc R . .
H15C H -0.0434 0.3696 0.2584 0.051 Uiso 1 1 calc R . .
C16 C 0.4276(2) 0.29269(19) 0.10573(10) 0.0262(3) Uani 1 1 d . . .
H16 H 0.5268 0.4129 0.1256 0.031 Uiso 1 1 calc R . .
C17 C 0.4050(2) 0.17903(19) 0.01244(10) 0.0276(3) Uani 1 1 d . . .
C18 C 0.2574(2) 0.0001(2) -0.01497(10) 0.0296(3) Uani 1 1 d . . .
H18 H 0.2405 -0.0783 -0.0773 0.036 Uiso 1 1 calc R . .
C19 C 0.1384(2) -0.06200(19) 0.04697(10) 0.0283(3) Uani 1 1 d . . .
H19 H 0.0395 -0.1823 0.0276 0.034 Uiso 1 1 calc R . .
C20 C 0.6946(2) 0.4099(2) -0.01640(12) 0.0390(4) Uani 1 1 d . . .
H20A H 0.6625 0.5076 0.0087 0.058 Uiso 1 1 calc R . .
H20B H 0.7666 0.4296 -0.0688 0.058 Uiso 1 1 calc R . .
H20C H 0.7717 0.4067 0.0342 0.058 Uiso 1 1 calc R . .
C21 C 0.5084(2) 0.1156(2) -0.14249(10) 0.0366(4) Uani 1 1 d . . .
H21A H 0.5335 0.0219 -0.1323 0.055 Uiso 1 1 calc R . .
H21B H 0.6023 0.1797 -0.1782 0.055 Uiso 1 1 calc R . .
H21C H 0.3806 0.0608 -0.1786 0.055 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3499(17) . ?
N1 C5 1.3817(18) . ?
N1 B1 1.6463(19) . ?
N2 C17 1.3787(19) . ?
N2 C20 1.448(2) . ?
N2 C21 1.4565(19) . ?
B1 C11 1.612(2) . ?
B1 C12 1.627(2) . ?
B1 C14 1.631(2) . ?
C1 C2 1.415(2) . ?
C1 C10 1.439(2) . ?
C2 C3 1.350(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(2) . ?
C3 H3 0.9500 . ?
C4 C9 1.411(2) . ?
C4 C5 1.418(2) . ?
C5 C6 1.407(2) . ?
C6 C7 1.373(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.362(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C19 1.3991(19) . ?
C10 C11 1.4039(19) . ?
C11 C16 1.387(2) . ?
C12 C13 1.522(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.529(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.4146(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.415(2) . ?
C18 C19 1.373(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 120.41(12) . . ?
C1 N1 B1 111.00(11) . . ?
C5 N1 B1 128.60(11) . . ?
C17 N2 C20 119.47(12) . . ?
C17 N2 C21 119.53(13) . . ?
C20 N2 C21 117.75(13) . . ?
C11 B1 C12 112.77(11) . . ?
C11 B1 C14 111.99(11) . . ?
C12 B1 C14 113.36(11) . . ?
C11 B1 N1 96.40(10) . . ?
C12 B1 N1 110.20(11) . . ?
C14 B1 N1 110.91(11) . . ?
N1 C1 C2 120.91(13) . . ?
N1 C1 C10 111.66(12) . . ?
C2 C1 C10 127.42(13) . . ?
C3 C2 C1 119.69(14) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.73(13) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C9 C4 C3 122.73(14) . . ?
C9 C4 C5 119.05(14) . . ?
C3 C4 C5 118.22(13) . . ?
N1 C5 C6 121.02(13) . . ?
N1 C5 C4 119.96(13) . . ?
C6 C5 C4 119.02(13) . . ?
C7 C6 C5 119.98(14) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 121.21(15) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 119.84(14) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 120.89(15) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C19 C10 C11 121.21(13) . . ?
C19 C10 C1 128.35(13) . . ?
C11 C10 C1 110.44(12) . . ?
C16 C11 C10 118.72(13) . . ?
C16 C11 B1 130.84(12) . . ?
C10 C11 B1 110.44(12) . . ?
C13 C12 B1 116.72(12) . . ?
C13 C12 H12A 108.1 . . ?
B1 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
B1 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 B1 115.93(12) . . ?
C15 C14 H14A 108.3 . . ?
B1 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
B1 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 C17 121.15(13) . . ?
C11 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
N2 C17 C16 121.09(13) . . ?
N2 C17 C18 120.61(13) . . ?
C16 C17 C18 118.29(13) . . ?
C19 C18 C17 121.07(13) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C10 119.55(13) . . ?
C18 C19 H19 120.2 . . ?
C10 C19 H19 120.2 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 B1 C11 1.78(13) . . . . ?
C5 N1 B1 C11 -178.51(12) . . . . ?
C1 N1 B1 C12 -115.36(12) . . . . ?
C5 N1 B1 C12 64.34(16) . . . . ?
C1 N1 B1 C14 118.28(12) . . . . ?
C5 N1 B1 C14 -62.01(17) . . . . ?
C5 N1 C1 C2 -2.56(19) . . . . ?
B1 N1 C1 C2 177.17(12) . . . . ?
C5 N1 C1 C10 177.82(11) . . . . ?
B1 N1 C1 C10 -2.45(15) . . . . ?
N1 C1 C2 C3 2.5(2) . . . . ?
C10 C1 C2 C3 -177.97(13) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C9 178.63(14) . . . . ?
C2 C3 C4 C5 -2.0(2) . . . . ?
C1 N1 C5 C6 -179.52(12) . . . . ?
B1 N1 C5 C6 0.8(2) . . . . ?
C1 N1 C5 C4 0.34(19) . . . . ?
B1 N1 C5 C4 -179.34(12) . . . . ?
C9 C4 C5 N1 -178.69(12) . . . . ?
C3 C4 C5 N1 1.91(19) . . . . ?
C9 C4 C5 C6 1.2(2) . . . . ?
C3 C4 C5 C6 -178.22(13) . . . . ?
N1 C5 C6 C7 178.96(13) . . . . ?
C4 C5 C6 C7 -0.9(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C4 -0.2(2) . . . . ?
C3 C4 C9 C8 178.75(14) . . . . ?
C5 C4 C9 C8 -0.6(2) . . . . ?
N1 C1 C10 C19 -177.28(13) . . . . ?
C2 C1 C10 C19 3.1(2) . . . . ?
N1 C1 C10 C11 2.07(16) . . . . ?
C2 C1 C10 C11 -177.52(13) . . . . ?
C19 C10 C11 C16 -0.97(19) . . . . ?
C1 C10 C11 C16 179.62(12) . . . . ?
C19 C10 C11 B1 178.65(12) . . . . ?
C1 C10 C11 B1 -0.76(15) . . . . ?
C12 B1 C11 C16 -65.90(18) . . . . ?
C14 B1 C11 C16 63.39(19) . . . . ?
N1 B1 C11 C16 179.02(13) . . . . ?
C12 B1 C11 C10 114.54(13) . . . . ?
C14 B1 C11 C10 -116.17(13) . . . . ?
N1 B1 C11 C10 -0.54(13) . . . . ?
C11 B1 C12 C13 -62.49(17) . . . . ?
C14 B1 C12 C13 168.93(13) . . . . ?
N1 B1 C12 C13 43.96(16) . . . . ?
C11 B1 C14 C15 62.26(16) . . . . ?
C12 B1 C14 C15 -168.76(12) . . . . ?
N1 B1 C14 C15 -44.17(16) . . . . ?
C10 C11 C16 C17 1.0(2) . . . . ?
B1 C11 C16 C17 -178.54(13) . . . . ?
C20 N2 C17 C16 14.0(2) . . . . ?
C21 N2 C17 C16 173.16(13) . . . . ?
C20 N2 C17 C18 -166.99(13) . . . . ?
C21 N2 C17 C18 -7.8(2) . . . . ?
C11 C16 C17 N2 178.40(12) . . . . ?
C11 C16 C17 C18 -0.6(2) . . . . ?
N2 C17 C18 C19 -178.78(13) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
C17 C18 C19 C10 -0.3(2) . . . . ?
C11 C10 C19 C18 0.6(2) . . . . ?
C1 C10 C19 C18 179.90(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
