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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3a
_database_code_depnum_ccdc_archive 'CCDC 1581758'
_audit_update_record             
;
2017-10-24 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;

_audit_creation_date             2017-10-04T17:28:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C16 H12 B N'
_chemical_formula_sum            'C16 H12 B N'
_chemical_formula_weight         229.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1772(7)
_cell_length_b                   7.8477(5)
_cell_length_c                   15.4070(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.891(4)
_cell_angle_gamma                90
_cell_volume                     1164.24(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    64
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 1 0.122
-1 0 3 0.215
2 0 -1 0.179
1 0 -9 0.273
-3 0 -4 0.212
-3 0 1 0.219
0 -1 0 0.12
0 1 0 0.192
3 3 -4 0.177
2 -6 -3 0.148


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  1.963
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.01
_diffrn_orient_matrix_ub_12      0
_diffrn_orient_matrix_ub_13      0
_diffrn_orient_matrix_ub_21      0
_diffrn_orient_matrix_ub_22      0.01
_diffrn_orient_matrix_ub_23      0
_diffrn_orient_matrix_ub_31      0
_diffrn_orient_matrix_ub_32      0
_diffrn_orient_matrix_ub_33      0.01
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.08
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_number            25671
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.349
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             2671
_reflns_number_gt                1784
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²+0.5012P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.099
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1524
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C12C C 0.78047(18) 0.4009(2) 0.21772(12) 0.0286(4) Uani 1 1 d . . . . .
C1 C 0.79483(19) 0.3553(2) 0.30835(12) 0.0315(4) Uani 1 1 d . . . . .
H1 H 0.7212 0.2973 0.3211 0.038 Uiso 1 1 calc R U . . .
C2 C 0.91428(19) 0.3936(2) 0.37904(13) 0.0365(5) Uani 1 1 d . . . . .
H2 H 0.9223 0.3618 0.44 0.044 Uiso 1 1 calc R U . . .
C3 C 1.0233(2) 0.4786(3) 0.36179(15) 0.0409(5) Uani 1 1 d . . . . .
H3 H 1.1031 0.5115 0.411 0.049 Uiso 1 1 calc R U . . .
C4 C 1.0142(2) 0.5140(2) 0.27333(15) 0.0391(5) Uani 1 1 d . . . . .
H4 H 1.0898 0.5694 0.2617 0.047 Uiso 1 1 calc R U . . .
C4A C 0.89643(19) 0.4709(2) 0.19900(13) 0.0328(4) Uani 1 1 d . . . . .
C5 C 0.8999(2) 0.4828(2) 0.10650(14) 0.0384(5) Uani 1 1 d . . . . .
H5 H 0.9748 0.5404 0.0951 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7991(2) 0.4138(2) 0.03611(14) 0.0385(5) Uani 1 1 d . . . . .
H6 H 0.8096 0.4067 -0.0229 0.046 Uiso 1 1 calc R U . . .
C12A C 0.52774(18) 0.3489(2) 0.15606(12) 0.0283(4) Uani 1 1 d . . . . .
C12 C 0.49846(19) 0.4256(2) 0.22970(12) 0.0319(4) Uani 1 1 d . . . . .
H12 H 0.5674 0.4927 0.2723 0.038 Uiso 1 1 calc R U . . .
C11 C 0.37016(19) 0.4047(2) 0.24116(13) 0.0360(5) Uani 1 1 d . . . . .
H11 H 0.3524 0.4564 0.292 0.043 Uiso 1 1 calc R U . . .
C10 C 0.26711(19) 0.3092(3) 0.17920(14) 0.0372(5) Uani 1 1 d . . . . .
H10 H 0.1812 0.289 0.1893 0.045 Uiso 1 1 calc R U . . .
C9 C 0.2913(2) 0.2446(2) 0.10340(14) 0.0375(5) Uani 1 1 d . . . . .
H9 H 0.2192 0.1834 0.0597 0.045 Uiso 1 1 calc R U . . .
C8A C 0.41886(19) 0.2655(2) 0.08782(13) 0.0325(4) Uani 1 1 d . . . . .
C8 C 0.4334(2) 0.2191(3) 0.00125(14) 0.0404(5) Uani 1 1 d . . . . .
H8 H 0.3622 0.1546 -0.0413 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5455(2) 0.2649(3) -0.02064(14) 0.0428(5) Uani 1 1 d . . . . .
H7 H 0.5482 0.2461 -0.0809 0.051 Uiso 1 1 calc R U . . .
B1 B 0.6684(2) 0.3473(3) 0.05129(15) 0.0348(5) Uani 1 1 d . . . . .
N1 N 0.65906(15) 0.36422(19) 0.14279(10) 0.0291(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C12C C1 1.402(2) . ?
C12C C4A 1.414(2) . ?
C12C N1 1.421(2) . ?
C1 C2 1.377(3) . ?
C1 H1 0.95 . ?
C2 C3 1.392(3) . ?
C2 H2 0.95 . ?
C3 C4 1.364(3) . ?
C3 H3 0.95 . ?
C4 C4A 1.405(3) . ?
C4 H4 0.95 . ?
C4A C5 1.440(3) . ?
C5 C6 1.342(3) . ?
C5 H5 0.95 . ?
C6 B1 1.516(3) . ?
C6 H6 0.95 . ?
C12A C12 1.399(2) . ?
C12A C8A 1.416(2) . ?
C12A N1 1.421(2) . ?
C12 C11 1.383(3) . ?
C12 H12 0.95 . ?
C11 C10 1.387(3) . ?
C11 H11 0.95 . ?
C10 C9 1.366(3) . ?
C10 H10 0.95 . ?
C9 C8A 1.404(3) . ?
C9 H9 0.95 . ?
C8A C8 1.436(3) . ?
C8 C7 1.339(3) . ?
C8 H8 0.95 . ?
C7 B1 1.521(3) . ?
C7 H7 0.95 . ?
B1 N1 1.450(2) . ?

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 C12C C4A 118.53(17) . . ?
C1 C12C N1 122.69(16) . . ?
C4A C12C N1 118.48(16) . . ?
C2 C1 C12C 120.83(18) . . ?
C2 C1 H1 119.6 . . ?
C12C C1 H1 119.6 . . ?
C1 C2 C3 120.50(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.20(18) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C4A 121.95(18) . . ?
C3 C4 H4 119 . . ?
C4A C4 H4 119 . . ?
C4 C4A C12C 118.39(17) . . ?
C4 C4A C5 120.21(17) . . ?
C12C C4A C5 121.12(17) . . ?
C6 C5 C4A 121.08(17) . . ?
C6 C5 H5 119.5 . . ?
C4A C5 H5 119.5 . . ?
C5 C6 B1 119.58(18) . . ?
C5 C6 H6 120.2 . . ?
B1 C6 H6 120.2 . . ?
C12 C12A C8A 118.66(16) . . ?
C12 C12A N1 122.50(16) . . ?
C8A C12A N1 118.59(15) . . ?
C11 C12 C12A 120.69(18) . . ?
C11 C12 H12 119.7 . . ?
C12A C12 H12 119.7 . . ?
C12 C11 C10 120.72(18) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C9 C10 C11 118.89(17) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C10 C9 C8A 122.36(18) . . ?
C10 C9 H9 118.8 . . ?
C8A C9 H9 118.8 . . ?
C9 C8A C12A 118.13(17) . . ?
C9 C8A C8 120.54(17) . . ?
C12A C8A C8 121.04(16) . . ?
C7 C8 C8A 121.19(18) . . ?
C7 C8 H8 119.4 . . ?
C8A C8 H8 119.4 . . ?
C8 C7 B1 119.83(18) . . ?
C8 C7 H7 120.1 . . ?
B1 C7 H7 120.1 . . ?
N1 B1 C6 117.11(18) . . ?
N1 B1 C7 116.75(18) . . ?
C6 B1 C7 126.14(18) . . ?
C12A N1 C12C 120.76(14) . . ?
C12A N1 B1 119.54(15) . . ?
C12C N1 B1 119.68(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A C12C C1 C2 6.5(3) . . . . ?
N1 C12C C1 C2 -179.88(16) . . . . ?
C12C C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 -4.1(3) . . . . ?
C2 C3 C4 C4A 1.6(3) . . . . ?
C3 C4 C4A C12C 5.0(3) . . . . ?
C3 C4 C4A C5 -169.08(18) . . . . ?
C1 C12C C4A C4 -8.9(3) . . . . ?
N1 C12C C4A C4 177.28(16) . . . . ?
C1 C12C C4A C5 165.13(17) . . . . ?
N1 C12C C4A C5 -8.7(3) . . . . ?
C4 C4A C5 C6 167.73(18) . . . . ?
C12C C4A C5 C6 -6.2(3) . . . . ?
C4A C5 C6 B1 9.9(3) . . . . ?
C8A C12A C12 C11 7.0(3) . . . . ?
N1 C12A C12 C11 -178.71(16) . . . . ?
C12A C12 C11 C10 -0.9(3) . . . . ?
C12 C11 C10 C9 -4.0(3) . . . . ?
C11 C10 C9 C8A 2.7(3) . . . . ?
C10 C9 C8A C12A 3.4(3) . . . . ?
C10 C9 C8A C8 -170.41(18) . . . . ?
C12 C12A C8A C9 -8.2(3) . . . . ?
N1 C12A C8A C9 177.33(15) . . . . ?
C12 C12A C8A C8 165.64(17) . . . . ?
N1 C12A C8A C8 -8.9(3) . . . . ?
C9 C8A C8 C7 168.23(19) . . . . ?
C12A C8A C8 C7 -5.4(3) . . . . ?
C8A C8 C7 B1 8.1(3) . . . . ?
C5 C6 B1 N1 0.7(3) . . . . ?
C5 C6 B1 C7 -179.61(19) . . . . ?
C8 C7 B1 N1 2.9(3) . . . . ?
C8 C7 B1 C6 -176.83(19) . . . . ?
C12 C12A N1 C12C 23.8(2) . . . . ?
C8A C12A N1 C12C -161.96(16) . . . . ?
C12 C12A N1 B1 -154.37(17) . . . . ?
C8A C12A N1 B1 19.9(2) . . . . ?
C1 C12C N1 C12A 27.5(2) . . . . ?
C4A C12C N1 C12A -158.88(16) . . . . ?
C1 C12C N1 B1 -154.33(17) . . . . ?
C4A C12C N1 B1 19.3(2) . . . . ?
C6 B1 N1 C12A 162.81(16) . . . . ?
C7 B1 N1 C12A -16.9(3) . . . . ?
C6 B1 N1 C12C -15.3(3) . . . . ?
C7 B1 N1 C12C 164.92(16) . . . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/diethylether'
