# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1480541'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 B F2 N2'
_chemical_formula_sum            'C33 H27 B F2 N2'
_chemical_formula_weight         500.38

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'
F F 0.0171 0.0103 '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'
_symmetry_space_group_name_Hall  '-p 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2790(4)
_cell_length_b                   8.3562(4)
_cell_length_c                   19.2301(9)
_cell_angle_alpha                100.217(2)
_cell_angle_beta                 98.258(2)
_cell_angle_gamma                96.502(2)
_cell_volume                     1282.48(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    9358
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.45
_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9789
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      220(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            37665
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         27.10
_reflns_number_total             5440
_reflns_number_gt                4089
_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)+(0.0780P)²+2.2000P] 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         5440
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0769
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.2091
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
F1 F 0.1507(3) 0.1576(2) 0.21148(11) 0.0578(5) Uani 1 1 d . . .
N1 N 0.0840(3) 0.3650(3) 0.30322(13) 0.0425(6) Uani 1 1 d . . .
C1 C 0.0846(4) 0.3016(4) 0.36372(17) 0.0448(7) Uani 1 1 d . . .
B1 B 0.1900(4) 0.3235(4) 0.2450(2) 0.0444(7) Uani 1 1 d . . .
N2 N 0.1520(3) 0.4323(3) 0.18960(13) 0.0413(5) Uani 1 1 d . . .
F2 F 0.3563(2) 0.3531(3) 0.27476(11) 0.0581(5) Uani 1 1 d . . .
C2 C -0.0215(4) 0.3768(4) 0.40529(17) 0.0486(7) Uani 1 1 d . . .
H2A H -0.0408 0.3561 0.4501 0.058 Uiso 1 1 calc R . .
C3 C -0.0923(4) 0.4856(4) 0.36959(17) 0.0470(7) Uani 1 1 d . . .
C4 C -0.0265(4) 0.4795(3) 0.30508(16) 0.0429(6) Uani 1 1 d . . .
C5 C -0.0518(3) 0.5643(3) 0.24886(16) 0.0417(6) Uani 1 1 d . . .
C6 C 0.0341(3) 0.5395(3) 0.19130(16) 0.0410(6) Uani 1 1 d . . .
C7 C 0.0259(4) 0.6048(4) 0.12747(18) 0.0470(7) Uani 1 1 d . . .
C8 C 0.1383(4) 0.5375(4) 0.08935(17) 0.0456(7) Uani 1 1 d . . .
H8A H 0.1591 0.5578 0.0447 0.055 Uiso 1 1 calc R . .
C9 C 0.2170(4) 0.4328(3) 0.12877(16) 0.0432(6) Uani 1 1 d . . .
C10 C 0.1781(4) 0.1707(4) 0.37692(17) 0.0470(7) Uani 1 1 d . . .
H10A H 0.2474 0.1352 0.3444 0.056 Uiso 1 1 calc R . .
C11 C 0.1704(4) 0.0980(4) 0.43313(18) 0.0498(7) Uani 1 1 d . . .
H11A H 0.1072 0.1412 0.4669 0.060 Uiso 1 1 calc R . .
C12 C 0.2508(4) -0.0416(4) 0.44683(19) 0.0512(7) Uani 1 1 d . . .
C13 C 0.2821(5) -0.0681(5) 0.5170(2) 0.0647(10) Uani 1 1 d . . .
H13A H 0.2491 0.0028 0.5543 0.078 Uiso 1 1 calc R . .
C14 C 0.3613(6) -0.1981(7) 0.5316(3) 0.0914(16) Uani 1 1 d . . .
H14A H 0.3866 -0.2133 0.5790 0.110 Uiso 1 1 calc R . .
C15 C 0.4031(6) -0.3059(6) 0.4758(4) 0.0967(19) Uani 1 1 d . . .
H15A H 0.4546 -0.3959 0.4856 0.116 Uiso 1 1 calc R . .
C16 C 0.3707(5) -0.2838(5) 0.4064(3) 0.0822(14) Uani 1 1 d . . .
H16A H 0.3997 -0.3583 0.3691 0.099 Uiso 1 1 calc R . .
C17 C 0.2959(5) -0.1524(4) 0.3916(2) 0.0643(10) Uani 1 1 d . . .
H17A H 0.2746 -0.1366 0.3441 0.077 Uiso 1 1 calc R . .
C18 C 0.3494(4) 0.3414(3) 0.11190(17) 0.0448(7) Uani 1 1 d . . .
H18A H 0.3914 0.2784 0.1444 0.054 Uiso 1 1 calc R . .
C19 C 0.4149(4) 0.3420(4) 0.05247(17) 0.0459(7) Uani 1 1 d . . .
H19A H 0.3705 0.4050 0.0205 0.055 Uiso 1 1 calc R . .
C20 C 0.5497(4) 0.2534(4) 0.03256(18) 0.0460(7) Uani 1 1 d . . .
C21 C 0.5548(4) 0.1969(4) -0.03907(19) 0.0532(8) Uani 1 1 d . . .
H21A H 0.4757 0.2224 -0.0741 0.064 Uiso 1 1 calc R . .
C22 C 0.6728(4) 0.1043(4) -0.0602(2) 0.0594(9) Uani 1 1 d . . .
H22A H 0.6723 0.0646 -0.1092 0.071 Uiso 1 1 calc R . .
C23 C 0.7913(4) 0.0702(4) -0.0095(2) 0.0654(10) Uani 1 1 d . . .
H23A H 0.8710 0.0056 -0.0239 0.078 Uiso 1 1 calc R . .
C24 C 0.7946(4) 0.1296(5) 0.0622(2) 0.0663(10) Uani 1 1 d . . .
H24A H 0.8786 0.1093 0.0966 0.080 Uiso 1 1 calc R . .
C25 C 0.6729(4) 0.2200(4) 0.0837(2) 0.0583(8) Uani 1 1 d . . .
H25A H 0.6734 0.2588 0.1327 0.070 Uiso 1 1 calc R . .
C26 C -0.1732(4) 0.6845(3) 0.25023(16) 0.0422(6) Uani 1 1 d . . .
C27 C -0.3423(4) 0.6310(4) 0.23391(17) 0.0477(7) Uani 1 1 d . . .
H27A H -0.3815 0.5179 0.2228 0.057 Uiso 1 1 calc R . .
C28 C -0.4526(4) 0.7428(4) 0.23394(19) 0.0545(8) Uani 1 1 d . . .
H28A H -0.5663 0.7052 0.2218 0.065 Uiso 1 1 calc R . .
C29 C -0.3979(4) 0.9093(4) 0.2515(2) 0.0576(9) Uani 1 1 d . . .
H29A H -0.4738 0.9850 0.2521 0.069 Uiso 1 1 calc R . .
C30 C -0.2301(4) 0.9638(4) 0.2682(2) 0.0606(9) Uani 1 1 d . . .
H30A H -0.1917 1.0771 0.2800 0.073 Uiso 1 1 calc R . .
C31 C -0.1189(4) 0.8522(4) 0.2675(2) 0.0540(8) Uani 1 1 d . . .
H31A H -0.0052 0.8904 0.2790 0.065 Uiso 1 1 calc R . .
C32 C -0.2161(5) 0.5890(5) 0.3967(2) 0.0644(10) Uani 1 1 d . . .
H32A H -0.2236 0.5792 0.4457 0.097 Uiso 1 1 calc R . .
H32B H -0.3231 0.5516 0.3668 0.097 Uiso 1 1 calc R . .
H32C H -0.1815 0.7030 0.3951 0.097 Uiso 1 1 calc R . .
C33 C -0.0819(5) 0.7243(5) 0.1031(2) 0.0594(9) Uani 1 1 d . . .
H33A H -0.0751 0.7288 0.0535 0.089 Uiso 1 1 calc R . .
H33B H -0.0448 0.8325 0.1327 0.089 Uiso 1 1 calc R . .
H33C H -0.1951 0.6888 0.1072 0.089 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
F1 B1 1.401(4) . ?
N1 C1 1.361(4) . ?
N1 C4 1.396(4) . ?
N1 B1 1.536(4) . ?
C1 C2 1.398(4) . ?
C1 C10 1.447(4) . ?
B1 F2 1.389(4) . ?
B1 N2 1.540(4) . ?
N2 C9 1.357(4) . ?
N2 C6 1.397(3) . ?
C2 C3 1.367(4) . ?
C2 H2A 0.9400 . ?
C3 C4 1.420(4) . ?
C3 C32 1.505(4) . ?
C4 C5 1.399(4) . ?
C5 C6 1.397(4) . ?
C5 C26 1.498(4) . ?
C6 C7 1.425(4) . ?
C7 C8 1.374(4) . ?
C7 C33 1.504(4) . ?
C8 C9 1.410(4) . ?
C8 H8A 0.9400 . ?
C9 C18 1.447(4) . ?
C10 C11 1.336(5) . ?
C10 H10A 0.9400 . ?
C11 C12 1.452(4) . ?
C11 H11A 0.9400 . ?
C12 C13 1.398(5) . ?
C12 C17 1.403(5) . ?
C13 C14 1.380(5) . ?
C13 H13A 0.9400 . ?
C14 C15 1.384(8) . ?
C14 H14A 0.9400 . ?
C15 C16 1.372(8) . ?
C15 H15A 0.9400 . ?
C16 C17 1.373(5) . ?
C16 H16A 0.9400 . ?
C17 H17A 0.9400 . ?
C18 C19 1.334(4) . ?
C18 H18A 0.9400 . ?
C19 C20 1.466(4) . ?
C19 H19A 0.9400 . ?
C20 C21 1.383(5) . ?
C20 C25 1.400(5) . ?
C21 C22 1.376(4) . ?
C21 H21A 0.9400 . ?
C22 C23 1.372(6) . ?
C22 H22A 0.9400 . ?
C23 C24 1.375(6) . ?
C23 H23A 0.9400 . ?
C24 C25 1.392(5) . ?
C24 H24A 0.9400 . ?
C25 H25A 0.9400 . ?
C26 C31 1.388(4) . ?
C26 C27 1.394(4) . ?
C27 C28 1.378(4) . ?
C27 H27A 0.9400 . ?
C28 C29 1.379(5) . ?
C28 H28A 0.9400 . ?
C29 C30 1.384(5) . ?
C29 H29A 0.9400 . ?
C30 C31 1.383(4) . ?
C30 H30A 0.9400 . ?
C31 H31A 0.9400 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?

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 C4 107.4(2) . . ?
C1 N1 B1 126.4(3) . . ?
C4 N1 B1 126.2(3) . . ?
N1 C1 C2 109.4(3) . . ?
N1 C1 C10 122.1(3) . . ?
C2 C1 C10 128.4(3) . . ?
F2 B1 F1 108.3(3) . . ?
F2 B1 N1 110.4(3) . . ?
F1 B1 N1 110.6(3) . . ?
F2 B1 N2 110.8(3) . . ?
F1 B1 N2 109.6(3) . . ?
N1 B1 N2 107.1(2) . . ?
C9 N2 C6 108.3(2) . . ?
C9 N2 B1 126.5(2) . . ?
C6 N2 B1 125.0(2) . . ?
C3 C2 C1 108.2(3) . . ?
C3 C2 H2A 125.9 . . ?
C1 C2 H2A 125.9 . . ?
C2 C3 C4 107.1(3) . . ?
C2 C3 C32 124.2(3) . . ?
C4 C3 C32 128.7(3) . . ?
N1 C4 C5 119.6(3) . . ?
N1 C4 C3 107.9(3) . . ?
C5 C4 C3 132.4(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 C26 119.2(3) . . ?
C4 C5 C26 119.5(3) . . ?
N2 C6 C5 120.6(3) . . ?
N2 C6 C7 107.6(2) . . ?
C5 C6 C7 131.8(3) . . ?
C8 C7 C6 107.0(3) . . ?
C8 C7 C33 124.1(3) . . ?
C6 C7 C33 128.9(3) . . ?
C7 C8 C9 108.2(3) . . ?
C7 C8 H8A 125.9 . . ?
C9 C8 H8A 125.9 . . ?
N2 C9 C8 108.8(3) . . ?
N2 C9 C18 122.8(3) . . ?
C8 C9 C18 128.3(3) . . ?
C11 C10 C1 123.1(3) . . ?
C11 C10 H10A 118.5 . . ?
C1 C10 H10A 118.5 . . ?
C10 C11 C12 126.0(3) . . ?
C10 C11 H11A 117.0 . . ?
C12 C11 H11A 117.0 . . ?
C13 C12 C17 118.9(3) . . ?
C13 C12 C11 119.1(3) . . ?
C17 C12 C11 121.9(3) . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C15 119.4(5) . . ?
C13 C14 H14A 120.3 . . ?
C15 C14 H14A 120.3 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
C15 C16 C17 119.8(5) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C16 C17 C12 120.4(4) . . ?
C16 C17 H17A 119.8 . . ?
C12 C17 H17A 119.8 . . ?
C19 C18 C9 123.2(3) . . ?
C19 C18 H18A 118.4 . . ?
C9 C18 H18A 118.4 . . ?
C18 C19 C20 125.9(3) . . ?
C18 C19 H19A 117.1 . . ?
C20 C19 H19A 117.1 . . ?
C21 C20 C25 118.2(3) . . ?
C21 C20 C19 119.5(3) . . ?
C25 C20 C19 122.3(3) . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21A 119.2 . . ?
C20 C21 H21A 119.2 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22A 120.2 . . ?
C21 C22 H22A 120.2 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23A 119.7 . . ?
C24 C23 H23A 119.7 . . ?
C23 C24 C25 119.7(4) . . ?
C23 C24 H24A 120.1 . . ?
C25 C24 H24A 120.1 . . ?
C24 C25 C20 120.2(4) . . ?
C24 C25 H25A 119.9 . . ?
C20 C25 H25A 119.9 . . ?
C31 C26 C27 118.5(3) . . ?
C31 C26 C5 120.4(3) . . ?
C27 C26 C5 121.1(3) . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27A 119.8 . . ?
C26 C27 H27A 119.8 . . ?
C27 C28 C29 120.7(3) . . ?
C27 C28 H28A 119.6 . . ?
C29 C28 H28A 119.6 . . ?
C28 C29 C30 119.3(3) . . ?
C28 C29 H29A 120.4 . . ?
C30 C29 H29A 120.4 . . ?
C31 C30 C29 120.2(3) . . ?
C31 C30 H30A 119.9 . . ?
C29 C30 H30A 119.9 . . ?
C30 C31 C26 120.7(3) . . ?
C30 C31 H31A 119.6 . . ?
C26 C31 H31A 119.6 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C7 C33 H33A 109.5 . . ?
C7 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C7 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.070
