# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_PBDP2
_database_code_depnum_ccdc_archive 'CCDC 1503390'
_audit_update_record             
;
2016-09-07 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H25 B1 F2 N2'
_chemical_formula_sum            'C30 H25 B1 F2 N2'
_chemical_formula_weight         462.33

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'
F F 0.0171 0.0103 '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                   7.1985(10)
_cell_length_b                   11.4552(16)
_cell_length_c                   14.805(2)
_cell_angle_alpha                78.169(5)
_cell_angle_beta                 81.599(5)
_cell_angle_gamma                88.276(4)
_cell_volume                     1182.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            brownish
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9746
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_process_details   SADABS

_exptl_special_details           ?

_diffrn_ambient_temperature      100(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-AXS platform'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15330
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_sigmaI/netI    0.1038
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4733
_reflns_number_gt                2455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_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 
 [0.00000+1.00000exp(3.00(sinθ/λ)²)]/ 
   [σ²(Fo²)+0.0400+0.0000*P+(0.0662P)²+0.0000sinθ/λ] 
 where P = 0.10000Fo² + 0.90000Fc² 
;
_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         4733
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.368
_refine_ls_restrained_S_all      1.368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C17 C 0.2733(4) 1.2148(3) 0.1961(2) 0.0277(7) Uani 1 1 d . . .
C16 C 0.2445(4) 1.3277(3) 0.2221(2) 0.0298(7) Uani 1 1 d . . .
C19 C 0.2207(5) 1.5321(3) 0.1077(2) 0.0323(8) Uani 1 1 d . . .
C18 C 0.2320(4) 1.4398(3) 0.1573(2) 0.0339(8) Uani 1 1 d . . .
C22 C 0.1726(5) 1.7510(4) -0.1111(2) 0.0470(10) Uani 1 1 d . . .
H22 H 0.1580 1.7499 -0.1737 0.056 Uiso 1 1 calc R . .
C21 C 0.1822(5) 1.6455(3) -0.0484(2) 0.0362(8) Uani 1 1 d . . .
H21 H 0.1719 1.5721 -0.0677 0.043 Uiso 1 1 calc R . .
C20 C 0.2070(4) 1.6448(3) 0.0433(2) 0.0298(7) Uani 1 1 d . . .
C11 C 0.2615(4) 0.9896(3) 0.4558(2) 0.0259(7) Uani 1 1 d . . .
C14 C 0.2474(4) 1.1839(3) 0.3516(2) 0.0255(7) Uani 1 1 d . . .
C10 C 0.2612(4) 0.9012(3) 0.5383(2) 0.0264(7) Uani 1 1 d . . .
C13 C 0.2417(4) 1.1147(3) 0.4415(2) 0.0263(7) Uani 1 1 d . . .
C9 C 0.2812(4) 0.7912(3) 0.5096(2) 0.0264(7) Uani 1 1 d . . .
C30 C 0.3156(4) 0.7238(3) 0.3510(2) 0.0293(7) Uani 1 1 d . . .
H30A H 0.1985 0.7192 0.3255 0.044 Uiso 1 1 calc R . .
H30B H 0.3436 0.6456 0.3877 0.044 Uiso 1 1 calc R . .
H30C H 0.4184 0.7477 0.2998 0.044 Uiso 1 1 calc R . .
C12 C 0.2950(4) 0.8134(3) 0.4119(2) 0.0247(7) Uani 1 1 d . . .
C28 C 0.2065(5) 1.4092(3) 0.3711(2) 0.0353(8) Uani 1 1 d . . .
H28A H 0.1999 1.4851 0.3268 0.053 Uiso 1 1 calc R . .
H28B H 0.3138 1.4106 0.4047 0.053 Uiso 1 1 calc R . .
H28C H 0.0905 1.3975 0.4157 0.053 Uiso 1 1 calc R . .
C29 C 0.3039(5) 1.1924(3) 0.0995(2) 0.0346(8) Uani 1 1 d . . .
H29A H 0.4386 1.1962 0.0760 0.052 Uiso 1 1 calc R . .
H29B H 0.2376 1.2531 0.0592 0.052 Uiso 1 1 calc R . .
H29C H 0.2558 1.1132 0.0998 0.052 Uiso 1 1 calc R . .
C26 C 0.2450(5) 0.9129(3) 0.6380(2) 0.0364(8) Uani 1 1 d . . .
H26A H 0.1203 0.9436 0.6575 0.055 Uiso 1 1 calc R . .
H26B H 0.3413 0.9680 0.6445 0.055 Uiso 1 1 calc R . .
H26C H 0.2629 0.8345 0.6772 0.055 Uiso 1 1 calc R . .
C24 C 0.2040(5) 1.8606(3) 0.0064(3) 0.0428(9) Uani 1 1 d . . .
H24 H 0.2084 1.9347 0.0253 0.051 Uiso 1 1 calc R . .
C25 C 0.2178(5) 1.7544(3) 0.0710(2) 0.0360(8) Uani 1 1 d . . .
H25 H 0.2345 1.7562 0.1332 0.043 Uiso 1 1 calc R . .
C23 C 0.1839(5) 1.8589(3) -0.0842(3) 0.0478(10) Uani 1 1 d . . .
H23 H 0.1779 1.9316 -0.1281 0.057 Uiso 1 1 calc R . .
C7 C 0.2825(4) 0.5846(3) 0.6250(2) 0.0311(8) Uani 1 1 d . . .
C8 C 0.2864(4) 0.6770(3) 0.5709(2) 0.0287(7) Uani 1 1 d . . .
C1 C 0.1873(4) 0.3727(3) 0.6814(2) 0.0306(7) Uani 1 1 d . . .
H1 H 0.1329 0.3747 0.6263 0.037 Uiso 1 1 calc R . .
C5 C 0.3492(4) 0.4697(3) 0.7762(2) 0.0306(7) Uani 1 1 d . . .
H5 H 0.4072 0.5384 0.7864 0.037 Uiso 1 1 calc R . .
C6 C 0.2745(4) 0.4753(3) 0.6941(2) 0.0278(7) Uani 1 1 d . . .
F2 F 0.1448(3) 0.95453(15) 0.23821(12) 0.0350(5) Uani 1 1 d . . .
F1 F 0.4624(3) 0.96923(15) 0.22559(12) 0.0370(5) Uani 1 1 d . . .
N2 N 0.2731(3) 1.1297(2) 0.27334(16) 0.0245(6) Uani 1 1 d . . .
N1 N 0.2832(3) 0.9319(2) 0.37961(16) 0.0244(6) Uani 1 1 d . . .
B1 B 0.2939(5) 0.9939(3) 0.2755(2) 0.0276(8) Uani 1 1 d . . .
C15 C 0.2300(4) 1.3088(3) 0.3192(2) 0.0296(7) Uani 1 1 d . . .
C4 C 0.3403(5) 0.3665(3) 0.8428(2) 0.0332(8) Uani 1 1 d . . .
H4 H 0.3928 0.3645 0.8984 0.040 Uiso 1 1 calc R . .
C3 C 0.2555(5) 0.2653(3) 0.8300(2) 0.0332(8) Uani 1 1 d . . .
H3 H 0.2490 0.1942 0.8765 0.040 Uiso 1 1 calc R . .
C2 C 0.1806(5) 0.2693(3) 0.7486(2) 0.0349(8) Uani 1 1 d . . .
H2 H 0.1239 0.2000 0.7388 0.042 Uiso 1 1 calc R . .
C27 C 0.2154(5) 1.1724(3) 0.5245(2) 0.0350(8) Uani 1 1 d . . .
H27A H 0.2157 1.2593 0.5035 0.052 Uiso 1 1 calc R . .
H27B H 0.3180 1.1487 0.5613 0.052 Uiso 1 1 calc R . .
H27C H 0.0953 1.1470 0.5630 0.052 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
C17 N2 1.342(4) . ?
C17 C16 1.425(4) . ?
C17 C29 1.488(4) . ?
C16 C15 1.398(4) . ?
C16 C18 1.445(5) . ?
C19 C18 1.166(4) . ?
C19 C20 1.450(5) . ?
C22 C21 1.372(5) . ?
C22 C23 1.383(5) . ?
C21 C20 1.393(4) . ?
C20 C25 1.406(4) . ?
C11 N1 1.407(3) . ?
C11 C13 1.411(4) . ?
C11 C10 1.418(4) . ?
C14 C13 1.397(4) . ?
C14 N2 1.410(4) . ?
C14 C15 1.421(4) . ?
C10 C9 1.407(4) . ?
C10 C26 1.497(4) . ?
C13 C27 1.497(4) . ?
C9 C12 1.406(4) . ?
C9 C8 1.433(4) . ?
C30 C12 1.489(4) . ?
C12 N1 1.349(4) . ?
C28 C15 1.502(4) . ?
C24 C23 1.374(5) . ?
C24 C25 1.395(5) . ?
C7 C8 1.187(4) . ?
C7 C6 1.442(4) . ?
C1 C2 1.379(4) . ?
C1 C6 1.407(4) . ?
C5 C4 1.372(4) . ?
C5 C6 1.389(4) . ?
F2 B1 1.401(4) . ?
F1 B1 1.379(4) . ?
N2 B1 1.553(4) . ?
N1 B1 1.551(4) . ?
C4 C3 1.385(4) . ?
C3 C2 1.383(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C17 C16 109.0(3) . . ?
N2 C17 C29 124.4(3) . . ?
C16 C17 C29 126.5(3) . . ?
C15 C16 C17 107.7(3) . . ?
C15 C16 C18 127.7(3) . . ?
C17 C16 C18 124.6(3) . . ?
C18 C19 C20 178.0(3) . . ?
C19 C18 C16 177.6(3) . . ?
C21 C22 C23 120.6(3) . . ?
C22 C21 C20 120.7(3) . . ?
C21 C20 C25 118.8(3) . . ?
C21 C20 C19 119.6(3) . . ?
C25 C20 C19 121.6(3) . . ?
N1 C11 C13 120.4(3) . . ?
N1 C11 C10 108.0(2) . . ?
C13 C11 C10 131.6(3) . . ?
C13 C14 N2 120.5(3) . . ?
C13 C14 C15 131.7(3) . . ?
N2 C14 C15 107.9(2) . . ?
C9 C10 C11 106.1(3) . . ?
C9 C10 C26 123.4(3) . . ?
C11 C10 C26 130.5(3) . . ?
C14 C13 C11 120.9(3) . . ?
C14 C13 C27 120.4(3) . . ?
C11 C13 C27 118.8(3) . . ?
C12 C9 C10 108.3(3) . . ?
C12 C9 C8 126.7(3) . . ?
C10 C9 C8 125.0(3) . . ?
N1 C12 C9 108.9(2) . . ?
N1 C12 C30 123.8(3) . . ?
C9 C12 C30 127.3(3) . . ?
C23 C24 C25 120.7(3) . . ?
C24 C25 C20 119.5(3) . . ?
C24 C23 C22 119.7(3) . . ?
C8 C7 C6 177.3(3) . . ?
C7 C8 C9 176.2(3) . . ?
C2 C1 C6 120.1(3) . . ?
C4 C5 C6 120.9(3) . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C7 120.5(3) . . ?
C1 C6 C7 121.2(3) . . ?
C17 N2 C14 108.8(2) . . ?
C17 N2 B1 125.3(2) . . ?
C14 N2 B1 126.0(2) . . ?
C12 N1 C11 108.7(2) . . ?
C12 N1 B1 125.3(2) . . ?
C11 N1 B1 125.9(2) . . ?
F1 B1 F2 109.9(2) . . ?
F1 B1 N1 110.7(3) . . ?
F2 B1 N1 109.4(3) . . ?
F1 B1 N2 110.8(3) . . ?
F2 B1 N2 109.5(2) . . ?
N1 B1 N2 106.4(2) . . ?
C16 C15 C14 106.6(3) . . ?
C16 C15 C28 122.5(3) . . ?
C14 C15 C28 130.9(3) . . ?
C5 C4 C3 120.7(3) . . ?
C2 C3 C4 119.0(3) . . ?
C1 C2 C3 120.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.055

_exptl_crystal_recrystallization_method 'layering method'
_exptl_crystal_preparation       ', Luminescent'
