# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_3
_database_code_depnum_ccdc_archive 'CCDC 1535184'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H23 B F2 N2'
_chemical_formula_weight         496.34

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           Monoclinic
_symmetry_space_group_name_H-M   'C2/c '

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

_cell_length_a                   16.140(5)
_cell_length_b                   14.391(4)
_cell_length_c                   21.159(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.057(3)
_cell_angle_gamma                90.00
_cell_volume                     4787(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6538
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22503
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.69
_reflns_number_total             5564
_reflns_number_gt                3792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1200P)²+6.4916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5564
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0878
_refine_ls_wR_factor_ref         0.2539
_refine_ls_wR_factor_gt          0.2144
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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 0.15894(15) 0.38438(14) 0.37353(9) 0.0546(6) Uani 1 1 d . . .
F2 F 0.27899(13) 0.40426(15) 0.33936(12) 0.0612(7) Uani 1 1 d . . .
N1 N 0.20227(16) 0.26142(18) 0.31172(12) 0.0325(6) Uani 1 1 d . . .
N2 N 0.14658(16) 0.40804(18) 0.25998(12) 0.0332(6) Uani 1 1 d . . .
C1 C 0.11296(18) 0.2624(2) 0.20292(14) 0.0296(6) Uani 1 1 d . . .
C15 C 0.23443(19) 0.1979(2) 0.35806(15) 0.0335(7) Uani 1 1 d . . .
C5 C 0.08168(18) 0.5128(2) 0.18444(15) 0.0315(7) Uani 1 1 d . . .
C2 C 0.10997(18) 0.3598(2) 0.20333(14) 0.0306(7) Uani 1 1 d . . .
C27 C 0.15504(18) 0.2129(2) 0.25844(14) 0.0306(7) Uani 1 1 d . . .
C6 C 0.0550(2) 0.6057(2) 0.16280(16) 0.0346(7) Uani 1 1 d . . .
C14 C 0.12956(19) 0.4991(2) 0.24848(15) 0.0326(7) Uani 1 1 d . . .
C3 C 0.07140(18) 0.4253(2) 0.15458(15) 0.0315(7) Uani 1 1 d . . .
C12 C 0.1335(2) 0.6598(2) 0.27042(17) 0.0450(8) Uani 1 1 d . . .
H12 H 0.1514 0.7097 0.2981 0.054 Uiso 1 1 calc R . .
C24 C 0.20832(19) 0.1072(2) 0.33645(15) 0.0330(7) Uani 1 1 d . . .
C17 C 0.3016(2) 0.1443(2) 0.46285(17) 0.0422(8) Uani 1 1 d . . .
H17 H 0.3325 0.1557 0.5048 0.051 Uiso 1 1 calc R . .
C23 C 0.23124(19) 0.0301(2) 0.38066(16) 0.0346(7) Uani 1 1 d . . .
C28 C 0.07023(19) 0.2106(2) 0.14378(14) 0.0305(7) Uani 1 1 d . . .
C16 C 0.28327(19) 0.2166(2) 0.42123(16) 0.0383(8) Uani 1 1 d . . .
H16 H 0.3021 0.2763 0.4336 0.046 Uiso 1 1 calc R . .
C25 C 0.15725(19) 0.1165(2) 0.27342(15) 0.0325(7) Uani 1 1 d . . .
C13 C 0.1559(2) 0.5737(2) 0.29222(16) 0.0406(8) Uani 1 1 d . . .
H13 H 0.1874 0.5635 0.3342 0.049 Uiso 1 1 calc R . .
C33 C 0.1183(2) 0.1638(2) 0.10721(16) 0.0395(8) Uani 1 1 d . . .
H33 H 0.1773 0.1648 0.1198 0.047 Uiso 1 1 calc R . .
C22 C 0.2118(2) -0.0637(2) 0.36499(19) 0.0460(9) Uani 1 1 d . . .
H22 H 0.1856 -0.0798 0.3226 0.055 Uiso 1 1 calc R . .
C19 C 0.2928(2) -0.0206(3) 0.49138(18) 0.0463(9) Uani 1 1 d . . .
H19 H 0.3200 -0.0066 0.5339 0.056 Uiso 1 1 calc R . .
C18 C 0.27533(19) 0.0509(2) 0.44510(16) 0.0373(7) Uani 1 1 d . . .
C11 C 0.0835(2) 0.6789(2) 0.20677(17) 0.0398(8) Uani 1 1 d . . .
C7 C 0.0017(2) 0.6281(3) 0.10269(17) 0.0453(8) Uani 1 1 d . . .
H7 H -0.0188 0.5807 0.0735 0.054 Uiso 1 1 calc R . .
B1 B 0.1993(2) 0.3669(2) 0.32305(17) 0.0348(8) Uani 1 1 d . . .
C29 C -0.0175(2) 0.2077(2) 0.12435(16) 0.0381(7) Uani 1 1 d . . .
H29 H -0.0504 0.2388 0.1485 0.046 Uiso 1 1 calc R . .
C32 C 0.0787(3) 0.1158(3) 0.05221(18) 0.0498(9) Uani 1 1 d . . .
H32 H 0.1112 0.0846 0.0278 0.060 Uiso 1 1 calc R . .
C4 C 0.0337(2) 0.4074(2) 0.08445(15) 0.0420(8) Uani 1 1 d . . .
H4A H -0.0271 0.4053 0.0774 0.063 Uiso 1 1 calc R . .
H4B H 0.0543 0.3492 0.0721 0.063 Uiso 1 1 calc R . .
H4C H 0.0498 0.4564 0.0588 0.063 Uiso 1 1 calc R . .
C21 C 0.2310(3) -0.1317(3) 0.4115(2) 0.0553(10) Uani 1 1 d . . .
H21 H 0.2172 -0.1931 0.4002 0.066 Uiso 1 1 calc R . .
C26 C 0.1085(2) 0.0396(2) 0.23404(17) 0.0438(8) Uani 1 1 d . . .
H26A H 0.0626 0.0655 0.2018 0.066 Uiso 1 1 calc R . .
H26B H 0.0859 -0.0010 0.2619 0.066 Uiso 1 1 calc R . .
H26C H 0.1456 0.0052 0.2131 0.066 Uiso 1 1 calc R . .
C10 C 0.0600(3) 0.7707(2) 0.1880(2) 0.0527(10) Uani 1 1 d . . .
H10 H 0.0796 0.8191 0.2165 0.063 Uiso 1 1 calc R . .
C30 C -0.0566(2) 0.1593(2) 0.06960(17) 0.0436(8) Uani 1 1 d . . .
H30 H -0.1156 0.1573 0.0571 0.052 Uiso 1 1 calc R . .
C31 C -0.0083(2) 0.1137(2) 0.03334(17) 0.0476(9) Uani 1 1 d . . .
H31 H -0.0347 0.0816 -0.0039 0.057 Uiso 1 1 calc R . .
C8 C -0.0208(3) 0.7180(3) 0.0860(2) 0.0565(10) Uani 1 1 d . . .
H8 H -0.0561 0.7309 0.0458 0.068 Uiso 1 1 calc R . .
C20 C 0.2705(2) -0.1104(3) 0.4749(2) 0.0541(10) Uani 1 1 d . . .
H20 H 0.2819 -0.1570 0.5061 0.065 Uiso 1 1 calc R . .
C9 C 0.0089(3) 0.7901(3) 0.1288(2) 0.0598(11) Uani 1 1 d . . .
H9 H -0.0059 0.8512 0.1171 0.072 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 1.393(4) . ?
F2 B1 1.365(4) . ?
N1 C15 1.355(4) . ?
N1 C27 1.397(4) . ?
N1 B1 1.539(4) . ?
N2 C14 1.350(4) . ?
N2 C2 1.395(4) . ?
N2 B1 1.530(4) . ?
C1 C2 1.404(4) . ?
C1 C27 1.410(4) . ?
C1 C28 1.486(4) . ?
C15 C24 1.415(4) . ?
C15 C16 1.415(4) . ?
C5 C3 1.403(4) . ?
C5 C14 1.414(4) . ?
C5 C6 1.446(4) . ?
C2 C3 1.431(4) . ?
C27 C25 1.422(4) . ?
C6 C7 1.402(5) . ?
C6 C11 1.412(5) . ?
C14 C13 1.419(4) . ?
C3 C4 1.493(4) . ?
C12 C13 1.343(5) . ?
C12 C11 1.432(5) . ?
C24 C25 1.407(4) . ?
C24 C23 1.445(4) . ?
C17 C16 1.351(5) . ?
C17 C18 1.434(5) . ?
C23 C22 1.408(5) . ?
C23 C18 1.420(5) . ?
C28 C29 1.384(4) . ?
C28 C33 1.387(4) . ?
C25 C26 1.497(4) . ?
C33 C32 1.380(5) . ?
C22 C21 1.373(5) . ?
C19 C20 1.365(5) . ?
C19 C18 1.404(5) . ?
C11 C10 1.406(5) . ?
C7 C8 1.368(5) . ?
C29 C30 1.377(5) . ?
C32 C31 1.370(5) . ?
C21 C20 1.383(6) . ?
C10 C9 1.363(6) . ?
C30 C31 1.377(5) . ?
C8 C9 1.389(6) . ?

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
C15 N1 C27 107.3(2) . . ?
C15 N1 B1 124.9(3) . . ?
C27 N1 B1 126.0(2) . . ?
C14 N2 C2 107.4(2) . . ?
C14 N2 B1 125.7(3) . . ?
C2 N2 B1 126.9(3) . . ?
C2 C1 C27 120.7(3) . . ?
C2 C1 C28 119.8(3) . . ?
C27 C1 C28 119.5(3) . . ?
N1 C15 C24 110.5(3) . . ?
N1 C15 C16 126.6(3) . . ?
C24 C15 C16 122.8(3) . . ?
C3 C5 C14 106.8(3) . . ?
C3 C5 C6 133.7(3) . . ?
C14 C5 C6 119.4(3) . . ?
N2 C2 C1 119.6(3) . . ?
N2 C2 C3 108.8(3) . . ?
C1 C2 C3 131.5(3) . . ?
N1 C27 C1 119.5(3) . . ?
N1 C27 C25 109.0(3) . . ?
C1 C27 C25 131.4(3) . . ?
C7 C6 C11 117.9(3) . . ?
C7 C6 C5 125.2(3) . . ?
C11 C6 C5 116.9(3) . . ?
N2 C14 C5 110.7(3) . . ?
N2 C14 C13 126.8(3) . . ?
C5 C14 C13 122.5(3) . . ?
C5 C3 C2 106.2(3) . . ?
C5 C3 C4 125.6(3) . . ?
C2 C3 C4 128.0(3) . . ?
C13 C12 C11 123.4(3) . . ?
C25 C24 C15 106.7(3) . . ?
C25 C24 C23 134.1(3) . . ?
C15 C24 C23 119.0(3) . . ?
C16 C17 C18 122.9(3) . . ?
C22 C23 C18 117.7(3) . . ?
C22 C23 C24 125.0(3) . . ?
C18 C23 C24 117.3(3) . . ?
C29 C28 C33 118.9(3) . . ?
C29 C28 C1 121.0(3) . . ?
C33 C28 C1 120.1(3) . . ?
C17 C16 C15 117.6(3) . . ?
C24 C25 C27 106.5(3) . . ?
C24 C25 C26 125.4(3) . . ?
C27 C25 C26 127.8(3) . . ?
C12 C13 C14 117.2(3) . . ?
C32 C33 C28 120.2(3) . . ?
C21 C22 C23 120.8(3) . . ?
C20 C19 C18 121.0(4) . . ?
C19 C18 C23 119.6(3) . . ?
C19 C18 C17 120.2(3) . . ?
C23 C18 C17 120.2(3) . . ?
C10 C11 C6 119.1(3) . . ?
C10 C11 C12 120.4(3) . . ?
C6 C11 C12 120.5(3) . . ?
C8 C7 C6 121.6(3) . . ?
F2 B1 F1 108.2(3) . . ?
F2 B1 N2 112.0(3) . . ?
F1 B1 N2 109.6(3) . . ?
F2 B1 N1 111.5(3) . . ?
F1 B1 N1 109.5(3) . . ?
N2 B1 N1 106.1(2) . . ?
C30 C29 C28 120.6(3) . . ?
C31 C32 C33 120.3(3) . . ?
C22 C21 C20 121.2(4) . . ?
C9 C10 C11 121.4(4) . . ?
C31 C30 C29 120.0(3) . . ?
C32 C31 C30 120.0(3) . . ?
C7 C8 C9 120.4(4) . . ?
C19 C20 C21 119.7(4) . . ?
C10 C9 C8 119.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.69
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.111
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1535183'
_audit_update_record             
;
2017-03-08 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            BODIPY
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 B F2 N2'
_chemical_formula_sum            'C26 H21 B F2 N2'
_chemical_formula_weight         410.26

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'
F F 0.0171 0.0103 '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   C2/c

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

_cell_length_a                   21.110(8)
_cell_length_b                   10.940(4)
_cell_length_c                   20.341(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.052(3)
_cell_angle_gamma                90.00
_cell_volume                     4146(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6878
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 Smart ApexII CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24017
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.59
_reflns_number_total             4783
_reflns_number_gt                3162
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0200P)²+38.5450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4783
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.2344
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.006
_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
B1 B 0.1216(2) 0.2054(5) 0.2147(3) 0.0421(11) Uani 1 1 d . . .
C1 C 0.3690(2) 0.1433(5) 0.4492(3) 0.0510(12) Uani 1 1 d . . .
H1A H 0.3785 0.1877 0.4936 0.077 Uiso 1 1 calc R . .
H1B H 0.3940 0.1810 0.4255 0.077 Uiso 1 1 calc R . .
H1C H 0.3850 0.0604 0.4619 0.077 Uiso 1 1 calc R . .
C2 C 0.2891(2) 0.1444(4) 0.3964(2) 0.0392(9) Uani 1 1 d . . .
C3 C 0.2345(2) 0.1204(4) 0.4158(2) 0.0381(9) Uani 1 1 d . . .
C4 C 0.2344(2) 0.0860(4) 0.4844(2) 0.0436(10) Uani 1 1 d . . .
C5 C 0.2969(3) 0.0691(5) 0.5534(3) 0.0588(13) Uani 1 1 d . . .
H5 H 0.3418 0.0776 0.5558 0.071 Uiso 1 1 calc R . .
C6 C 0.2924(4) 0.0406(5) 0.6166(3) 0.0708(17) Uani 1 1 d . . .
H6 H 0.3341 0.0310 0.6615 0.085 Uiso 1 1 calc R . .
C7 C 0.2256(4) 0.0258(5) 0.6138(3) 0.0726(17) Uani 1 1 d . . .
H7 H 0.2229 0.0067 0.6570 0.087 Uiso 1 1 calc R . .
C8 C 0.1638(3) 0.0392(5) 0.5478(3) 0.0639(15) Uani 1 1 d . . .
H8 H 0.1196 0.0274 0.5466 0.077 Uiso 1 1 calc R . .
C9 C 0.1662(3) 0.0708(4) 0.4817(3) 0.0494(11) Uani 1 1 d . . .
C10 C 0.1020(3) 0.0910(5) 0.4142(3) 0.0524(12) Uani 1 1 d . . .
H10 H 0.0583 0.0805 0.4143 0.063 Uiso 1 1 calc R . .
C11 C 0.1012(2) 0.1244(4) 0.3501(3) 0.0484(11) Uani 1 1 d . . .
H11 H 0.0583 0.1374 0.3068 0.058 Uiso 1 1 calc R . .
C12 C 0.1684(2) 0.1390(4) 0.3510(2) 0.0390(9) Uani 1 1 d . . .
C13 C 0.2544(2) 0.1755(4) 0.3196(2) 0.0367(9) Uani 1 1 d . . .
C14 C 0.2814(2) 0.2121(4) 0.2709(2) 0.0378(9) Uani 1 1 d . . .
C15 C 0.3605(2) 0.2042(4) 0.2970(2) 0.0410(10) Uani 1 1 d . . .
C16 C 0.3919(2) 0.0912(4) 0.3028(2) 0.0427(10) Uani 1 1 d . . .
H16 H 0.3638 0.0210 0.2911 0.051 Uiso 1 1 calc R . .
C17 C 0.4643(3) 0.0816(6) 0.3258(3) 0.0589(13) Uani 1 1 d . . .
H17 H 0.4851 0.0054 0.3289 0.071 Uiso 1 1 calc R . .
C18 C 0.5051(3) 0.1841(7) 0.3441(3) 0.0730(18) Uani 1 1 d . . .
H18 H 0.5542 0.1776 0.3603 0.088 Uiso 1 1 calc R . .
C19 C 0.4753(3) 0.2964(6) 0.3390(4) 0.0759(19) Uani 1 1 d . . .
H19 H 0.5041 0.3658 0.3518 0.091 Uiso 1 1 calc R . .
C20 C 0.4027(3) 0.3081(5) 0.3152(3) 0.0621(14) Uani 1 1 d . . .
H20 H 0.3824 0.3849 0.3113 0.075 Uiso 1 1 calc R . .
C21 C 0.2358(2) 0.2511(4) 0.1990(3) 0.0416(10) Uani 1 1 d . . .
C22 C 0.2486(3) 0.2888(4) 0.1386(3) 0.0500(11) Uani 1 1 d . . .
C23 C 0.3189(3) 0.2982(6) 0.1366(3) 0.0684(16) Uani 1 1 d . . .
H23A H 0.3455 0.2238 0.1552 0.103 Uiso 1 1 calc R . .
H23B H 0.3462 0.3654 0.1672 0.103 Uiso 1 1 calc R . .
H23C H 0.3098 0.3114 0.0863 0.103 Uiso 1 1 calc R . .
C24 C 0.1824(3) 0.3122(5) 0.0798(3) 0.0588(13) Uani 1 1 d . . .
H24 H 0.1741 0.3395 0.0331 0.071 Uiso 1 1 calc R . .
C25 C 0.1293(3) 0.2886(5) 0.1006(3) 0.0525(12) Uani 1 1 d . . .
C26 C 0.0501(3) 0.2993(6) 0.0539(3) 0.0729(17) Uani 1 1 d . . .
H26A H 0.0292 0.2191 0.0425 0.109 Uiso 1 1 calc R . .
H26B H 0.0395 0.3413 0.0085 0.109 Uiso 1 1 calc R . .
H26C H 0.0304 0.3442 0.0806 0.109 Uiso 1 1 calc R . .
F1 F 0.07696(14) 0.2941(3) 0.21762(16) 0.0609(8) Uani 1 1 d . . .
F2 F 0.08144(15) 0.1033(3) 0.17896(16) 0.0628(8) Uani 1 1 d . . .
N1 N 0.16073(18) 0.2528(3) 0.1719(2) 0.0425(8) Uani 1 1 d . . .
N2 N 0.18004(17) 0.1726(3) 0.29343(19) 0.0380(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
B1 F1 1.373(6) . ?
B1 F2 1.385(6) . ?
B1 N2 1.536(6) . ?
B1 N1 1.542(6) . ?
C1 C2 1.514(5) . ?
C2 C3 1.407(6) . ?
C2 C13 1.420(6) . ?
C3 C12 1.412(6) . ?
C3 C4 1.447(6) . ?
C4 C9 1.425(6) . ?
C4 C5 1.415(7) . ?
C5 C6 1.370(7) . ?
C6 C7 1.395(9) . ?
C7 C8 1.370(8) . ?
C8 C9 1.413(7) . ?
C9 C10 1.421(7) . ?
C10 C11 1.348(7) . ?
C11 C12 1.419(6) . ?
C12 N2 1.356(5) . ?
C13 N2 1.401(5) . ?
C13 C14 1.414(6) . ?
C14 C21 1.387(6) . ?
C14 C15 1.498(5) . ?
C15 C16 1.381(6) . ?
C15 C20 1.383(6) . ?
C16 C17 1.377(6) . ?
C17 C18 1.355(8) . ?
C18 C19 1.363(9) . ?
C19 C20 1.378(7) . ?
C21 N1 1.412(5) . ?
C21 C22 1.436(6) . ?
C22 C24 1.370(7) . ?
C22 C23 1.507(7) . ?
C24 C25 1.395(7) . ?
C25 N1 1.340(6) . ?
C25 C26 1.490(7) . ?

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
F1 B1 F2 109.2(4) . . ?
F1 B1 N2 110.5(4) . . ?
F2 B1 N2 110.6(4) . . ?
F1 B1 N1 110.4(4) . . ?
F2 B1 N1 109.5(4) . . ?
N2 B1 N1 106.7(3) . . ?
C3 C2 C13 106.6(3) . . ?
C3 C2 C1 125.9(4) . . ?
C13 C2 C1 127.4(4) . . ?
C12 C3 C2 107.0(4) . . ?
C12 C3 C4 119.3(4) . . ?
C2 C3 C4 133.8(4) . . ?
C9 C4 C5 118.6(5) . . ?
C9 C4 C3 116.9(4) . . ?
C5 C4 C3 124.5(4) . . ?
C6 C5 C4 121.0(6) . . ?
C7 C6 C5 120.3(6) . . ?
C8 C7 C6 120.3(5) . . ?
C7 C8 C9 121.1(6) . . ?
C4 C9 C10 120.5(4) . . ?
C4 C9 C8 118.6(5) . . ?
C10 C9 C8 120.9(5) . . ?
C11 C10 C9 123.3(4) . . ?
C10 C11 C12 117.4(4) . . ?
N2 C12 C3 110.2(4) . . ?
N2 C12 C11 127.2(4) . . ?
C3 C12 C11 122.6(4) . . ?
N2 C13 C14 119.3(4) . . ?
N2 C13 C2 108.6(4) . . ?
C14 C13 C2 132.0(4) . . ?
C21 C14 C13 121.2(4) . . ?
C21 C14 C15 119.8(4) . . ?
C13 C14 C15 119.0(4) . . ?
C16 C15 C20 119.3(4) . . ?
C16 C15 C14 119.5(4) . . ?
C20 C15 C14 121.2(4) . . ?
C17 C16 C15 120.6(5) . . ?
C18 C17 C16 119.4(5) . . ?
C19 C18 C17 120.9(5) . . ?
C18 C19 C20 120.5(5) . . ?
C19 C20 C15 119.2(5) . . ?
C14 C21 N1 120.7(4) . . ?
C14 C21 C22 132.3(4) . . ?
N1 C21 C22 106.9(4) . . ?
C24 C22 C21 106.0(4) . . ?
C24 C22 C23 125.2(5) . . ?
C21 C22 C23 128.8(5) . . ?
C22 C24 C25 109.6(5) . . ?
N1 C25 C24 108.9(4) . . ?
N1 C25 C26 123.3(5) . . ?
C24 C25 C26 127.8(5) . . ?
C25 N1 C21 108.6(4) . . ?
C25 N1 B1 125.8(4) . . ?
C21 N1 B1 125.2(4) . . ?
C12 N2 C13 107.6(3) . . ?
C12 N2 B1 125.6(4) . . ?
C13 N2 B1 126.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.214
