# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_Borebt1
_database_code_depnum_ccdc_archive 'CCDC 1029825'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 B F2 N2 S'
_chemical_formula_weight         376.22

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'
S S 0.1246 0.1234 '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'
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                   9.1766(9)
_cell_length_b                   9.2490(10)
_cell_length_c                   11.8304(13)
_cell_angle_alpha                109.989(10)
_cell_angle_beta                 96.898(9)
_cell_angle_gamma                99.154(9)
_cell_volume                     914.97(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1416
_cell_measurement_theta_min      3.2080
_cell_measurement_theta_max      26.0830

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            5832
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3210
_reflns_number_gt                2200
_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)+(0.0353P)²+0.0000P] 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         3210
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
S1 S 0.54940(7) 0.31372(7) 1.07304(6) 0.0566(2) Uani 1 1 d . . .
B1 B 0.1108(3) 0.2251(3) 0.9127(3) 0.0480(7) Uani 1 1 d . . .
F1 F 0.09264(16) 0.31602(15) 0.84128(13) 0.0697(5) Uani 1 1 d . . .
F2 F 0.00100(15) 0.23792(17) 0.98416(13) 0.0707(4) Uani 1 1 d . . .
N1 N 0.2686(2) 0.2894(2) 0.99548(17) 0.0437(5) Uani 1 1 d . . .
N2 N 0.09919(19) 0.0533(2) 0.83115(16) 0.0436(5) Uani 1 1 d . . .
C1 C 0.4674(3) 0.4712(3) 1.1416(2) 0.0514(6) Uani 1 1 d . . .
C2 C 0.5354(3) 0.6142(3) 1.2340(2) 0.0601(7) Uani 1 1 d . . .
H2 H 0.6365 0.6359 1.2690 0.072 Uiso 1 1 calc R . .
C3 C 0.4476(3) 0.7234(3) 1.2721(2) 0.0690(8) Uani 1 1 d . . .
H3 H 0.4904 0.8209 1.3333 0.083 Uiso 1 1 calc R . .
C4 C 0.2962(3) 0.6898(3) 1.2204(2) 0.0664(8) Uani 1 1 d . . .
H4 H 0.2395 0.7651 1.2486 0.080 Uiso 1 1 calc R . .
C5 C 0.2281(3) 0.5484(3) 1.1288(2) 0.0566(7) Uani 1 1 d . . .
H5 H 0.1268 0.5271 1.0944 0.068 Uiso 1 1 calc R . .
C6 C 0.3159(3) 0.4378(3) 1.0891(2) 0.0468(6) Uani 1 1 d . . .
C7 C 0.3799(2) 0.2098(3) 0.9766(2) 0.0468(6) Uani 1 1 d . . .
C8 C 0.3572(2) 0.0588(3) 0.8892(2) 0.0508(6) Uani 1 1 d . . .
H8 H 0.4375 0.0088 0.8781 0.061 Uiso 1 1 calc R . .
C9 C 0.2164(3) -0.0181(3) 0.8185(2) 0.0452(6) Uani 1 1 d . . .
C10 C 0.1967(2) -0.1815(3) 0.7310(2) 0.0453(6) Uani 1 1 d . . .
C11 C 0.2680(3) -0.2124(3) 0.6317(3) 0.0675(8) Uani 1 1 d . . .
H11 H 0.3249 -0.1293 0.6181 0.081 Uiso 1 1 calc R . .
C12 C 0.2561(3) -0.3648(4) 0.5523(3) 0.0814(9) Uani 1 1 d . . .
H12 H 0.3031 -0.3837 0.4849 0.098 Uiso 1 1 calc R . .
C13 C 0.1756(3) -0.4881(3) 0.5725(3) 0.0759(9) Uani 1 1 d . . .
H13 H 0.1678 -0.5908 0.5191 0.091 Uiso 1 1 calc R . .
C14 C 0.1062(3) -0.4597(3) 0.6718(3) 0.0699(8) Uani 1 1 d . . .
H14 H 0.0523 -0.5437 0.6862 0.084 Uiso 1 1 calc R . .
C15 C 0.1156(3) -0.3085(3) 0.7503(2) 0.0600(7) Uani 1 1 d . . .
H15 H 0.0672 -0.2907 0.8170 0.072 Uiso 1 1 calc R . .
C16 C -0.0459(2) -0.0241(2) 0.7518(2) 0.0431(5) Uani 1 1 d . . .
C17 C -0.0721(3) -0.0197(3) 0.6375(2) 0.0571(7) Uani 1 1 d . . .
H17 H 0.0043 0.0291 0.6094 0.069 Uiso 1 1 calc R . .
C18 C -0.2123(3) -0.0878(3) 0.5628(2) 0.0675(8) Uani 1 1 d . . .
H18 H -0.2293 -0.0854 0.4845 0.081 Uiso 1 1 calc R . .
C19 C -0.3250(3) -0.1580(3) 0.6035(3) 0.0651(7) Uani 1 1 d . . .
H19 H -0.4186 -0.2049 0.5529 0.078 Uiso 1 1 calc R . .
C20 C -0.3001(3) -0.1592(3) 0.7194(3) 0.0789(9) Uani 1 1 d . . .
H20 H -0.3773 -0.2062 0.7478 0.095 Uiso 1 1 calc R . .
C21 C -0.1603(3) -0.0909(3) 0.7947(3) 0.0699(8) Uani 1 1 d . . .
H21 H -0.1442 -0.0903 0.8739 0.084 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
S1 C7 1.730(2) . ?
S1 C1 1.742(3) . ?
B1 F2 1.385(3) . ?
B1 F1 1.395(3) . ?
B1 N2 1.530(3) . ?
B1 N1 1.548(3) . ?
N1 C7 1.347(3) . ?
N1 C6 1.398(3) . ?
N2 C9 1.346(3) . ?
N2 C16 1.450(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.381(4) . ?
C3 C4 1.389(4) . ?
C4 C5 1.372(3) . ?
C5 C6 1.393(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.479(3) . ?
C10 C11 1.380(3) . ?
C10 C15 1.390(3) . ?
C11 C12 1.379(4) . ?
C12 C13 1.365(4) . ?
C13 C14 1.370(4) . ?
C14 C15 1.371(3) . ?
C16 C17 1.360(3) . ?
C16 C21 1.369(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.357(3) . ?
C19 C20 1.366(4) . ?
C20 C21 1.386(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
C7 S1 C1 90.50(11) . . ?
F2 B1 F1 108.2(2) . . ?
F2 B1 N2 110.93(19) . . ?
F1 B1 N2 110.4(2) . . ?
F2 B1 N1 110.0(2) . . ?
F1 B1 N1 108.65(19) . . ?
N2 B1 N1 108.67(18) . . ?
C7 N1 C6 112.72(18) . . ?
C7 N1 B1 122.0(2) . . ?
C6 N1 B1 125.04(18) . . ?
C9 N2 C16 120.36(19) . . ?
C9 N2 B1 124.41(18) . . ?
C16 N2 B1 114.62(16) . . ?
C2 C1 C6 121.5(2) . . ?
C2 C1 S1 127.9(2) . . ?
C6 C1 S1 110.55(19) . . ?
C3 C2 C1 117.6(2) . . ?
C2 C3 C4 121.0(3) . . ?
C5 C4 C3 121.7(3) . . ?
C4 C5 C6 117.7(2) . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 N1 113.1(2) . . ?
C5 C6 N1 126.4(2) . . ?
N1 C7 C8 122.4(2) . . ?
N1 C7 S1 113.10(18) . . ?
C8 C7 S1 124.53(17) . . ?
C9 C8 C7 120.8(2) . . ?
N2 C9 C8 120.6(2) . . ?
N2 C9 C10 120.75(19) . . ?
C8 C9 C10 118.6(2) . . ?
C11 C10 C15 118.1(2) . . ?
C11 C10 C9 120.2(2) . . ?
C15 C10 C9 121.5(2) . . ?
C12 C11 C10 120.8(2) . . ?
C13 C12 C11 120.2(3) . . ?
C12 C13 C14 119.7(3) . . ?
C13 C14 C15 120.5(3) . . ?
C14 C15 C10 120.6(3) . . ?
C17 C16 C21 119.7(2) . . ?
C17 C16 N2 119.8(2) . . ?
C21 C16 N2 120.3(2) . . ?
C16 C17 C18 120.2(2) . . ?
C19 C18 C17 120.3(3) . . ?
C18 C19 C20 119.6(2) . . ?
C19 C20 C21 120.4(3) . . ?
C16 C21 C20 119.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_Borebt2
_database_code_depnum_ccdc_archive 'CCDC 1029826'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 B F2 N2 S'
_chemical_formula_weight         404.27

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'
S S 0.1246 0.1234 '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'
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   P21/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                   11.3993(10)
_cell_length_b                   12.7664(9)
_cell_length_c                   15.0074(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.220(7)
_cell_angle_gamma                90.00
_cell_volume                     1942.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1629
_cell_measurement_theta_min      3.2010
_cell_measurement_theta_max      21.4810

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            12800
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3424
_reflns_number_gt                2009
_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)+(0.0407P)²+0.0000P] 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         3424
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
S1 S 0.82592(9) 0.60961(7) 0.10596(6) 0.0528(3) Uani 1 1 d . . .
F1 F 0.75496(19) 0.72248(14) 0.39387(13) 0.0638(6) Uani 1 1 d . . .
F2 F 0.94283(17) 0.78864(14) 0.40286(12) 0.0627(6) Uani 1 1 d . . .
N1 N 0.8134(2) 0.67947(18) 0.26253(17) 0.0396(6) Uani 1 1 d . . .
N2 N 0.7363(2) 0.85895(18) 0.27650(17) 0.0375(6) Uani 1 1 d . . .
C1 C 0.8521(3) 0.5220(2) 0.2017(2) 0.0455(8) Uani 1 1 d . . .
C2 C 0.8802(3) 0.4161(3) 0.2064(3) 0.0553(9) Uani 1 1 d . . .
H2 H 0.8874 0.3830 0.1539 0.066 Uiso 1 1 calc R . .
C3 C 0.8971(3) 0.3607(3) 0.2899(3) 0.0639(10) Uani 1 1 d . . .
H3 H 0.9154 0.2894 0.2937 0.077 Uiso 1 1 calc R . .
C4 C 0.8874(3) 0.4098(3) 0.3688(3) 0.0643(10) Uani 1 1 d . . .
H4 H 0.8998 0.3710 0.4248 0.077 Uiso 1 1 calc R . .
C5 C 0.8594(3) 0.5157(3) 0.3654(2) 0.0532(9) Uani 1 1 d . . .
H5 H 0.8527 0.5483 0.4183 0.064 Uiso 1 1 calc R . .
C6 C 0.8417(3) 0.5718(2) 0.2811(2) 0.0416(8) Uani 1 1 d . . .
C7 C 0.8034(3) 0.7103(2) 0.1739(2) 0.0392(7) Uani 1 1 d . . .
C8 C 0.7736(3) 0.8123(2) 0.1387(2) 0.0430(8) Uani 1 1 d . . .
H8 H 0.7799 0.8323 0.0815 0.052 Uiso 1 1 calc R . .
C9 C 0.7346(3) 0.8846(2) 0.1890(2) 0.0373(7) Uani 1 1 d . . .
C10 C 0.6924(3) 0.9904(2) 0.1428(2) 0.0399(7) Uani 1 1 d . . .
C11 C 0.7783(3) 1.0445(3) 0.1176(2) 0.0533(9) Uani 1 1 d . . .
H11 H 0.8570 1.0133 0.1276 0.064 Uiso 1 1 calc R . .
C12 C 0.7484(4) 1.1447(3) 0.0778(3) 0.0704(11) Uani 1 1 d . . .
H12 H 0.8075 1.1810 0.0624 0.084 Uiso 1 1 calc R . .
C13 C 0.6303(4) 1.1900(3) 0.0612(3) 0.0712(11) Uani 1 1 d . . .
H13 H 0.6100 1.2574 0.0349 0.085 Uiso 1 1 calc R . .
C14 C 0.5435(4) 1.1365(3) 0.0832(2) 0.0579(10) Uani 1 1 d . . .
H14 H 0.4634 1.1673 0.0705 0.069 Uiso 1 1 calc R . .
C15 C 0.5729(3) 1.0369(3) 0.1243(2) 0.0483(8) Uani 1 1 d . . .
H15 H 0.5131 1.0012 0.1395 0.058 Uiso 1 1 calc R . .
C16 C 0.6712(3) 0.9251(2) 0.3195(2) 0.0376(7) Uani 1 1 d . . .
C17 C 0.5461(3) 0.8948(2) 0.3047(2) 0.0444(8) Uani 1 1 d . . .
C18 C 0.4849(3) 0.9552(3) 0.3475(2) 0.0569(9) Uani 1 1 d . . .
H18 H 0.4026 0.9353 0.3404 0.068 Uiso 1 1 calc R . .
C19 C 0.5436(4) 1.0440(3) 0.4004(3) 0.0610(10) Uani 1 1 d . . .
H19 H 0.5006 1.0842 0.4282 0.073 Uiso 1 1 calc R . .
C20 C 0.6656(4) 1.0739(3) 0.4126(2) 0.0531(9) Uani 1 1 d . . .
H20 H 0.7039 1.1347 0.4483 0.064 Uiso 1 1 calc R . .
C21 C 0.7333(3) 1.0154(2) 0.3728(2) 0.0420(8) Uani 1 1 d . . .
C22 C 0.8635(3) 1.0512(3) 0.3841(2) 0.0616(10) Uani 1 1 d . . .
H22A H 0.8518 1.0858 0.3238 0.092 Uiso 1 1 calc R . .
H22B H 0.9206 0.9919 0.3964 0.092 Uiso 1 1 calc R . .
H22C H 0.9021 1.0991 0.4394 0.092 Uiso 1 1 calc R . .
C23 C 0.4746(3) 0.8033(3) 0.2368(3) 0.0662(10) Uani 1 1 d . . .
H23A H 0.5313 0.7431 0.2561 0.099 Uiso 1 1 calc R . .
H23B H 0.4511 0.8213 0.1686 0.099 Uiso 1 1 calc R . .
H23C H 0.3962 0.7877 0.2429 0.099 Uiso 1 1 calc R . .
B1 B 0.8124(4) 0.7632(3) 0.3382(3) 0.0440(9) 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
S1 C7 1.731(3) . ?
S1 C1 1.736(3) . ?
F1 B1 1.378(4) . ?
F2 B1 1.392(4) . ?
N1 C7 1.342(3) . ?
N1 C6 1.410(3) . ?
N1 B1 1.563(4) . ?
N2 C9 1.345(3) . ?
N2 C16 1.456(3) . ?
N2 B1 1.539(4) . ?
C1 C2 1.384(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.387(4) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.495(4) . ?
C10 C11 1.384(4) . ?
C10 C15 1.393(4) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.394(4) . ?
C16 C21 1.397(4) . ?
C17 C18 1.380(4) . ?
C17 C23 1.519(4) . ?
C18 C19 1.371(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.486(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C7 S1 C1 90.39(15) . . ?
C7 N1 C6 113.0(2) . . ?
C7 N1 B1 119.6(3) . . ?
C6 N1 B1 126.9(3) . . ?
C9 N2 C16 120.6(2) . . ?
C9 N2 B1 122.2(2) . . ?
C16 N2 B1 117.1(2) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 S1 128.3(3) . . ?
C6 C1 S1 111.2(2) . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 N1 127.5(3) . . ?
C1 C6 N1 112.0(3) . . ?
N1 C7 C8 123.2(3) . . ?
N1 C7 S1 113.4(2) . . ?
C8 C7 S1 123.4(2) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N2 C9 C8 120.3(3) . . ?
N2 C9 C10 122.1(3) . . ?
C8 C9 C10 117.7(3) . . ?
C11 C10 C15 118.9(3) . . ?
C11 C10 C9 117.4(3) . . ?
C15 C10 C9 123.7(3) . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C17 C16 C21 122.3(3) . . ?
C17 C16 N2 117.4(3) . . ?
C21 C16 N2 120.3(3) . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C23 120.7(3) . . ?
C16 C17 C23 121.1(3) . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 121.5(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C16 117.0(3) . . ?
C20 C21 C22 120.5(3) . . ?
C16 C21 C22 122.5(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F1 B1 F2 108.5(3) . . ?
F1 B1 N2 111.8(3) . . ?
F2 B1 N2 111.3(3) . . ?
F1 B1 N1 110.2(3) . . ?
F2 B1 N1 107.8(3) . . ?
N2 B1 N1 107.2(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
C7 S1 C1 C2 -179.4(3) . . . . ?
C7 S1 C1 C6 0.6(2) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
S1 C1 C2 C3 -179.8(2) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C4 C5 C6 N1 -179.6(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
S1 C1 C6 C5 -179.9(2) . . . . ?
C2 C1 C6 N1 179.7(3) . . . . ?
S1 C1 C6 N1 -0.3(3) . . . . ?
C7 N1 C6 C5 179.3(3) . . . . ?
B1 N1 C6 C5 8.0(5) . . . . ?
C7 N1 C6 C1 -0.2(3) . . . . ?
B1 N1 C6 C1 -171.6(3) . . . . ?
C6 N1 C7 C8 178.7(3) . . . . ?
B1 N1 C7 C8 -9.3(4) . . . . ?
C6 N1 C7 S1 0.7(3) . . . . ?
B1 N1 C7 S1 172.7(2) . . . . ?
C1 S1 C7 N1 -0.8(2) . . . . ?
C1 S1 C7 C8 -178.7(3) . . . . ?
N1 C7 C8 C9 -9.0(4) . . . . ?
S1 C7 C8 C9 168.8(2) . . . . ?
C16 N2 C9 C8 -167.4(3) . . . . ?
B1 N2 C9 C8 16.0(4) . . . . ?
C16 N2 C9 C10 13.1(4) . . . . ?
B1 N2 C9 C10 -163.5(3) . . . . ?
C7 C8 C9 N2 5.8(4) . . . . ?
C7 C8 C9 C10 -174.7(3) . . . . ?
N2 C9 C10 C11 126.4(3) . . . . ?
C8 C9 C10 C11 -53.0(4) . . . . ?
N2 C9 C10 C15 -53.3(4) . . . . ?
C8 C9 C10 C15 127.2(3) . . . . ?
C15 C10 C11 C12 2.1(5) . . . . ?
C9 C10 C11 C12 -177.6(3) . . . . ?
C10 C11 C12 C13 -1.3(5) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 1.3(6) . . . . ?
C13 C14 C15 C10 -0.5(5) . . . . ?
C11 C10 C15 C14 -1.2(4) . . . . ?
C9 C10 C15 C14 178.5(3) . . . . ?
C9 N2 C16 C17 99.1(3) . . . . ?
B1 N2 C16 C17 -84.2(3) . . . . ?
C9 N2 C16 C21 -80.6(3) . . . . ?
B1 N2 C16 C21 96.2(3) . . . . ?
C21 C16 C17 C18 -2.2(4) . . . . ?
N2 C16 C17 C18 178.2(3) . . . . ?
C21 C16 C17 C23 173.1(3) . . . . ?
N2 C16 C17 C23 -6.6(4) . . . . ?
C16 C17 C18 C19 2.0(5) . . . . ?
C23 C17 C18 C19 -173.3(3) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C19 C20 C21 C16 0.2(4) . . . . ?
C19 C20 C21 C22 178.0(3) . . . . ?
C17 C16 C21 C20 1.1(4) . . . . ?
N2 C16 C21 C20 -179.3(2) . . . . ?
C17 C16 C21 C22 -176.6(3) . . . . ?
N2 C16 C21 C22 3.0(4) . . . . ?
C9 N2 B1 F1 -151.1(3) . . . . ?
C16 N2 B1 F1 32.2(4) . . . . ?
C9 N2 B1 F2 87.5(3) . . . . ?
C16 N2 B1 F2 -89.2(3) . . . . ?
C9 N2 B1 N1 -30.1(4) . . . . ?
C16 N2 B1 N1 153.2(2) . . . . ?
C7 N1 B1 F1 148.2(3) . . . . ?
C6 N1 B1 F1 -41.0(4) . . . . ?
C7 N1 B1 F2 -93.6(3) . . . . ?
C6 N1 B1 F2 77.2(4) . . . . ?
C7 N1 B1 N2 26.3(4) . . . . ?
C6 N1 B1 N2 -162.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_Borebt3
_database_code_depnum_ccdc_archive 'CCDC 1029827'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 B F2 N3 S'
_chemical_formula_weight         419.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   15.8955(3)
_cell_length_b                   9.83109(15)
_cell_length_c                   26.4038(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4126.12(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8430
_cell_measurement_theta_min      5.5380
_cell_measurement_theta_max      71.8250

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7313
_exptl_absorpt_correction_T_max  0.8249
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            25319
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         67.25
_reflns_number_total             3693
_reflns_number_gt                3085
_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)+(0.0482P)²+1.7701P] 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         3693
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
S1 S 0.30863(4) 1.21293(5) 0.66230(2) 0.06058(18) Uani 1 1 d . . .
B1 B 0.44065(14) 0.9097(2) 0.59357(8) 0.0466(5) Uani 1 1 d . . .
F1 F 0.52232(7) 0.94698(12) 0.58088(4) 0.0615(3) Uani 1 1 d . . .
F2 F 0.40246(9) 0.85122(12) 0.55222(4) 0.0705(4) Uani 1 1 d . . .
N1 N 0.39091(9) 1.03921(15) 0.60901(6) 0.0441(4) Uani 1 1 d . . .
N2 N 0.44200(10) 0.81127(14) 0.63928(6) 0.0439(4) Uani 1 1 d . . .
N3 N 0.65407(11) 0.36891(17) 0.59292(7) 0.0616(5) Uani 1 1 d . . .
C1 C 0.32824(12) 1.25150(19) 0.59875(8) 0.0516(5) Uani 1 1 d . . .
C2 C 0.30309(13) 1.3654(2) 0.57143(9) 0.0617(6) Uani 1 1 d . . .
H2 H 0.2720 1.4344 0.5866 0.074 Uiso 1 1 calc R . .
C3 C 0.32562(14) 1.3728(2) 0.52111(9) 0.0650(6) Uani 1 1 d . . .
H3 H 0.3096 1.4480 0.5020 0.078 Uiso 1 1 calc R . .
C4 C 0.37182(14) 1.2700(2) 0.49859(9) 0.0617(5) Uani 1 1 d . . .
H4 H 0.3869 1.2781 0.4647 0.074 Uiso 1 1 calc R . .
C5 C 0.39596(13) 1.1561(2) 0.52521(8) 0.0536(5) Uani 1 1 d . . .
H5 H 0.4265 1.0871 0.5096 0.064 Uiso 1 1 calc R . .
C6 C 0.37351(11) 1.14705(18) 0.57585(7) 0.0454(4) Uani 1 1 d . . .
C7 C 0.36041(12) 1.05769(18) 0.65588(7) 0.0472(4) Uani 1 1 d . . .
C8 C 0.36783(13) 0.96150(19) 0.69376(7) 0.0519(5) Uani 1 1 d . . .
H8 H 0.3452 0.9789 0.7256 0.062 Uiso 1 1 calc R . .
C9 C 0.40877(12) 0.83914(19) 0.68480(7) 0.0458(4) Uani 1 1 d . . .
C10 C 0.41198(12) 0.73790(19) 0.72678(7) 0.0478(4) Uani 1 1 d . . .
C11 C 0.44149(13) 0.7777(2) 0.77413(8) 0.0571(5) Uani 1 1 d . . .
H11 H 0.4618 0.8655 0.7788 0.069 Uiso 1 1 calc R . .
C12 C 0.44074(15) 0.6875(2) 0.81404(8) 0.0649(6) Uani 1 1 d . . .
H12 H 0.4621 0.7140 0.8453 0.078 Uiso 1 1 calc R . .
C13 C 0.40874(15) 0.5585(2) 0.80803(9) 0.0673(6) Uani 1 1 d . . .
H13 H 0.4071 0.4987 0.8353 0.081 Uiso 1 1 calc R . .
C14 C 0.37909(14) 0.5186(2) 0.76132(9) 0.0641(6) Uani 1 1 d . . .
H14 H 0.3572 0.4316 0.7571 0.077 Uiso 1 1 calc R . .
C15 C 0.38166(13) 0.6068(2) 0.72067(8) 0.0551(5) Uani 1 1 d . . .
H15 H 0.3630 0.5782 0.6891 0.066 Uiso 1 1 calc R . .
C16 C 0.49336(11) 0.69158(17) 0.63117(7) 0.0423(4) Uani 1 1 d . . .
C17 C 0.56980(12) 0.67510(18) 0.65556(7) 0.0467(4) Uani 1 1 d . . .
H17 H 0.5862 0.7376 0.6801 0.056 Uiso 1 1 calc R . .
C18 C 0.62213(12) 0.56738(19) 0.64401(7) 0.0482(4) Uani 1 1 d . . .
H18 H 0.6727 0.5577 0.6614 0.058 Uiso 1 1 calc R . .
C19 C 0.60049(12) 0.47226(18) 0.60658(7) 0.0456(4) Uani 1 1 d . . .
C20 C 0.52152(12) 0.48758(19) 0.58377(7) 0.0495(5) Uani 1 1 d . . .
H20 H 0.5035 0.4235 0.5602 0.059 Uiso 1 1 calc R . .
C21 C 0.46998(12) 0.59578(19) 0.59549(7) 0.0491(4) Uani 1 1 d . . .
H21 H 0.4185 0.6046 0.5791 0.059 Uiso 1 1 calc R . .
C22 C 0.73550(16) 0.3564(3) 0.61623(11) 0.0879(8) Uani 1 1 d . . .
H22A H 0.7683 0.4360 0.6089 0.132 Uiso 1 1 calc R . .
H22B H 0.7636 0.2775 0.6031 0.132 Uiso 1 1 calc R . .
H22C H 0.7289 0.3473 0.6522 0.132 Uiso 1 1 calc R . .
C23 C 0.63191(17) 0.2732(2) 0.55363(10) 0.0733(7) Uani 1 1 d . . .
H23A H 0.5836 0.2216 0.5640 0.110 Uiso 1 1 calc R . .
H23B H 0.6783 0.2127 0.5477 0.110 Uiso 1 1 calc R . .
H23C H 0.6191 0.3216 0.5230 0.110 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
S1 C7 1.7422(18) . ?
S1 C1 1.748(2) . ?
B1 F2 1.375(2) . ?
B1 F1 1.390(3) . ?
B1 N2 1.547(3) . ?
B1 N1 1.553(2) . ?
N1 C7 1.342(2) . ?
N1 C6 1.402(2) . ?
N2 C9 1.341(2) . ?
N2 C16 1.448(2) . ?
N3 C19 1.374(2) . ?
N3 C22 1.439(3) . ?
N3 C23 1.444(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.377(3) . ?
C5 C6 1.387(3) . ?
C7 C8 1.381(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.491(3) . ?
C10 C15 1.385(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.377(3) . ?
C12 C13 1.375(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.380(3) . ?
C16 C21 1.383(2) . ?
C16 C17 1.385(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.403(3) . ?
C19 C20 1.400(3) . ?
C20 C21 1.378(3) . ?

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
C7 S1 C1 90.71(9) . . ?
F2 B1 F1 109.33(16) . . ?
F2 B1 N2 111.33(16) . . ?
F1 B1 N2 109.88(16) . . ?
F2 B1 N1 109.06(16) . . ?
F1 B1 N1 108.84(16) . . ?
N2 B1 N1 108.37(15) . . ?
C7 N1 C6 113.72(15) . . ?
C7 N1 B1 122.49(16) . . ?
C6 N1 B1 123.79(15) . . ?
C9 N2 C16 121.37(15) . . ?
C9 N2 B1 124.46(15) . . ?
C16 N2 B1 113.63(14) . . ?
C19 N3 C22 120.57(18) . . ?
C19 N3 C23 121.29(18) . . ?
C22 N3 C23 118.10(19) . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 S1 128.41(17) . . ?
C6 C1 S1 110.43(15) . . ?
C3 C2 C1 117.9(2) . . ?
C2 C3 C4 120.9(2) . . ?
C5 C4 C3 121.5(2) . . ?
C4 C5 C6 118.2(2) . . ?
C5 C6 C1 120.28(18) . . ?
C5 C6 N1 126.86(17) . . ?
C1 C6 N1 112.86(17) . . ?
N1 C7 C8 122.97(17) . . ?
N1 C7 S1 112.28(14) . . ?
C8 C7 S1 124.73(14) . . ?
C7 C8 C9 120.66(17) . . ?
N2 C9 C8 120.96(17) . . ?
N2 C9 C10 121.10(16) . . ?
C8 C9 C10 117.90(16) . . ?
C15 C10 C11 118.90(18) . . ?
C15 C10 C9 121.50(18) . . ?
C11 C10 C9 119.48(18) . . ?
C12 C11 C10 120.2(2) . . ?
C13 C12 C11 120.6(2) . . ?
C12 C13 C14 119.5(2) . . ?
C13 C14 C15 120.5(2) . . ?
C14 C15 C10 120.3(2) . . ?
C21 C16 C17 118.23(17) . . ?
C21 C16 N2 120.17(16) . . ?
C17 C16 N2 121.40(16) . . ?
C18 C17 C16 121.04(17) . . ?
C17 C18 C19 121.26(17) . . ?
N3 C19 C20 121.48(17) . . ?
N3 C19 C18 121.72(18) . . ?
C20 C19 C18 116.80(17) . . ?
C21 C20 C19 121.29(17) . . ?
C20 C21 C16 121.26(18) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_Borebt4
_database_code_depnum_ccdc_archive 'CCDC 1029828'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 B F2 N3 O0 S'
_chemical_formula_weight         419.29

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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   '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                   12.1191(13)
_cell_length_b                   14.1236(14)
_cell_length_c                   11.9134(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.907(2)
_cell_angle_gamma                90.00
_cell_volume                     2002.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1711
_cell_measurement_theta_min      2.238
_cell_measurement_theta_max      21.105

_exptl_crystal_description       ABC
_exptl_crystal_colour            ABC
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9173
_exptl_absorpt_correction_T_max  0.9546
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            9921
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3521
_reflns_number_gt                1938
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0649P)²+0.0000P] 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         3521
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_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
B1 B 0.7825(3) 0.1022(3) 0.9604(3) 0.0526(10) Uani 1 1 d . . .
F1 F 0.84151(19) 0.1811(2) 0.93925(16) 0.1174(10) Uani 1 1 d . . .
F2 F 0.83828(18) 0.02193(19) 0.93867(15) 0.1076(9) Uani 1 1 d . . .
N1 N 0.77455(19) 0.10267(16) 1.08795(17) 0.0378(6) Uani 1 1 d . . .
N2 N 0.66395(19) 0.10207(16) 0.88825(17) 0.0404(6) Uani 1 1 d . . .
N3 N 0.1462(2) 0.20582(19) 0.6527(2) 0.0539(7) Uani 1 1 d . . .
S1 S 0.69343(7) 0.12544(6) 1.26955(6) 0.0543(3) Uani 1 1 d . . .
C1 C 0.9755(2) 0.0683(2) 1.1706(2) 0.0438(8) Uani 1 1 d . . .
H1 H 0.9953 0.0587 1.0998 0.053 Uiso 1 1 calc R . .
C2 C 1.0543(3) 0.0616(2) 1.2682(2) 0.0487(8) Uani 1 1 d . . .
H2 H 1.1285 0.0484 1.2635 0.058 Uiso 1 1 calc R . .
C3 C 1.0256(3) 0.0741(2) 1.3739(3) 0.0545(9) Uani 1 1 d . . .
H3 H 1.0806 0.0691 1.4396 0.065 Uiso 1 1 calc R . .
C4 C 0.9166(3) 0.0939(2) 1.3831(2) 0.0559(9) Uani 1 1 d . . .
H4 H 0.8972 0.1020 1.4544 0.067 Uiso 1 1 calc R . .
C5 C 0.8364(3) 0.1014(2) 1.2842(2) 0.0445(8) Uani 1 1 d . . .
C6 C 0.8657(2) 0.08972(19) 1.1777(2) 0.0384(7) Uani 1 1 d . . .
C7 C 0.6785(2) 0.1226(2) 1.1221(2) 0.0394(7) Uani 1 1 d . . .
C8 C 0.5786(2) 0.1381(2) 1.0458(2) 0.0401(7) Uani 1 1 d . . .
H8 H 0.5155 0.1574 1.0736 0.048 Uiso 1 1 calc R . .
C9 C 0.5707(2) 0.12563(19) 0.9291(2) 0.0386(7) Uani 1 1 d . . .
C10 C 0.4618(2) 0.14132(19) 0.8539(2) 0.0383(7) Uani 1 1 d . . .
C11 C 0.3620(2) 0.1160(2) 0.8872(2) 0.0417(7) Uani 1 1 d . . .
H11 H 0.3655 0.0847 0.9564 0.050 Uiso 1 1 calc R . .
C12 C 0.2587(2) 0.1355(2) 0.8220(2) 0.0431(7) Uani 1 1 d . . .
H12 H 0.1943 0.1163 0.8475 0.052 Uiso 1 1 calc R . .
C13 C 0.2480(2) 0.1839(2) 0.7177(2) 0.0415(7) Uani 1 1 d . . .
C14 C 0.3494(3) 0.2088(2) 0.6838(2) 0.0487(8) Uani 1 1 d . . .
H14 H 0.3469 0.2405 0.6150 0.058 Uiso 1 1 calc R . .
C15 C 0.4508(2) 0.1875(2) 0.7493(2) 0.0467(8) Uani 1 1 d . . .
H15 H 0.5156 0.2045 0.7231 0.056 Uiso 1 1 calc R . .
C16 C 0.0439(2) 0.1861(2) 0.6940(3) 0.0576(9) Uani 1 1 d . . .
H16A H 0.0458 0.2181 0.7654 0.086 Uiso 1 1 calc R . .
H16B H 0.0375 0.1191 0.7049 0.086 Uiso 1 1 calc R . .
H16C H -0.0194 0.2079 0.6391 0.086 Uiso 1 1 calc R . .
C17 C 0.1406(3) 0.2638(2) 0.5524(3) 0.0623(10) Uani 1 1 d . . .
H17A H 0.1793 0.2328 0.4995 0.093 Uiso 1 1 calc R . .
H17B H 0.1754 0.3239 0.5738 0.093 Uiso 1 1 calc R . .
H17C H 0.0634 0.2735 0.5171 0.093 Uiso 1 1 calc R . .
C18 C 0.6569(2) 0.0668(2) 0.7740(2) 0.0449(8) Uani 1 1 d . . .
C19 C 0.6057(3) -0.0179(3) 0.7419(3) 0.0602(9) Uani 1 1 d . . .
H19 H 0.5722 -0.0520 0.7932 0.072 Uiso 1 1 calc R . .
C20 C 0.6037(3) -0.0527(3) 0.6334(3) 0.0788(12) Uani 1 1 d . . .
H20 H 0.5694 -0.1106 0.6123 0.095 Uiso 1 1 calc R . .
C21 C 0.6519(3) -0.0030(3) 0.5565(3) 0.0795(13) Uani 1 1 d . . .
H21 H 0.6496 -0.0265 0.4832 0.095 Uiso 1 1 calc R . .
C22 C 0.7029(3) 0.0809(3) 0.5883(3) 0.0687(11) Uani 1 1 d . . .
H22 H 0.7349 0.1152 0.5359 0.082 Uiso 1 1 calc R . .
C23 C 0.7080(3) 0.1161(2) 0.6974(2) 0.0554(9) Uani 1 1 d . . .
H23 H 0.7455 0.1725 0.7192 0.066 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
B1 F2 1.370(4) . ?
B1 F1 1.373(4) . ?
B1 N2 1.528(4) . ?
B1 N1 1.540(4) . ?
N1 C7 1.334(3) . ?
N1 C6 1.396(3) . ?
N2 C9 1.354(3) . ?
N2 C18 1.436(3) . ?
N3 C13 1.362(3) . ?
N3 C17 1.439(4) . ?
N3 C16 1.444(3) . ?
S1 C7 1.732(3) . ?
S1 C5 1.742(3) . ?
C1 C2 1.361(4) . ?
C1 C6 1.383(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.375(4) . ?
C4 C5 1.382(4) . ?
C5 C6 1.391(4) . ?
C7 C8 1.386(4) . ?
C8 C9 1.386(3) . ?
C9 C10 1.465(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.390(4) . ?
C11 C12 1.371(4) . ?
C12 C13 1.403(4) . ?
C13 C14 1.409(4) . ?
C14 C15 1.359(4) . ?
C18 C19 1.369(4) . ?
C18 C23 1.384(4) . ?
C19 C20 1.378(4) . ?
C20 C21 1.369(5) . ?
C21 C22 1.356(5) . ?
C22 C23 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
F2 B1 F1 110.1(3) . . ?
F2 B1 N2 109.7(3) . . ?
F1 B1 N2 111.4(3) . . ?
F2 B1 N1 108.4(3) . . ?
F1 B1 N1 108.0(3) . . ?
N2 B1 N1 109.1(2) . . ?
C7 N1 C6 113.8(2) . . ?
C7 N1 B1 121.5(2) . . ?
C6 N1 B1 124.6(2) . . ?
C9 N2 C18 121.5(2) . . ?
C9 N2 B1 123.8(2) . . ?
C18 N2 B1 114.5(2) . . ?
C13 N3 C17 119.8(3) . . ?
C13 N3 C16 120.3(3) . . ?
C17 N3 C16 118.9(3) . . ?
C7 S1 C5 90.49(13) . . ?
C2 C1 C6 119.4(3) . . ?
C1 C2 C3 120.9(3) . . ?
C4 C3 C2 120.7(3) . . ?
C3 C4 C5 118.6(3) . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 S1 128.8(2) . . ?
C6 C5 S1 110.6(2) . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 N1 127.8(2) . . ?
C5 C6 N1 112.5(3) . . ?
N1 C7 C8 122.5(2) . . ?
N1 C7 S1 112.6(2) . . ?
C8 C7 S1 124.9(2) . . ?
C7 C8 C9 121.6(3) . . ?
N2 C9 C8 119.2(3) . . ?
N2 C9 C10 122.2(2) . . ?
C8 C9 C10 118.6(2) . . ?
C11 C10 C15 115.9(3) . . ?
C11 C10 C9 121.2(2) . . ?
C15 C10 C9 122.8(3) . . ?
C12 C11 C10 122.6(3) . . ?
C11 C12 C13 121.4(3) . . ?
N3 C13 C12 122.5(3) . . ?
N3 C13 C14 121.7(3) . . ?
C12 C13 C14 115.9(3) . . ?
C15 C14 C13 121.5(3) . . ?
C14 C15 C10 122.8(3) . . ?
C19 C18 C23 119.4(3) . . ?
C19 C18 N2 120.7(3) . . ?
C23 C18 N2 119.8(3) . . ?
C18 C19 C20 120.0(3) . . ?
C21 C20 C19 120.7(4) . . ?
C22 C21 C20 119.4(3) . . ?
C21 C22 C23 120.9(3) . . ?
C22 C23 C18 119.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_Borebt5
_database_code_depnum_ccdc_archive 'CCDC 1029829'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 B F2 N3 S'
_chemical_formula_weight         447.34

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'
S S 0.1246 0.1234 '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'
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   P21/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                   13.0949(9)
_cell_length_b                   12.1529(6)
_cell_length_c                   14.5043(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.475(7)
_cell_angle_gamma                90.00
_cell_volume                     2235.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1069
_cell_measurement_theta_min      3.3420
_cell_measurement_theta_max      21.6940

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            8077
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3941
_reflns_number_gt                2078
_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)+(0.0390P)²+0.0000P] 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         3941
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_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
S1 S 0.18891(8) 0.27310(8) 0.35837(6) 0.0673(3) Uani 1 1 d . . .
B1 B 0.3019(3) 0.4432(3) 0.6038(3) 0.0572(11) Uani 1 1 d . . .
F1 F 0.40861(16) 0.44760(16) 0.64096(15) 0.0898(8) Uani 1 1 d . . .
F2 F 0.25486(18) 0.40816(16) 0.67595(13) 0.0805(7) Uani 1 1 d . . .
N1 N 0.2751(2) 0.3583(2) 0.52167(18) 0.0479(7) Uani 1 1 d . . .
N2 N 0.25660(19) 0.5560(2) 0.56492(16) 0.0431(7) Uani 1 1 d . . .
C1 C 0.2779(3) 0.1933(3) 0.4403(2) 0.0532(9) Uani 1 1 d . . .
C2 C 0.3100(3) 0.0864(3) 0.4297(3) 0.0671(11) Uani 1 1 d . . .
H2 H 0.2862 0.0488 0.3725 0.081 Uiso 1 1 calc R . .
C3 C 0.3776(3) 0.0378(3) 0.5059(3) 0.0745(12) Uani 1 1 d . . .
H3 H 0.3992 -0.0343 0.5006 0.089 Uiso 1 1 calc R . .
C4 C 0.4145(3) 0.0936(3) 0.5906(3) 0.0730(12) Uani 1 1 d . . .
H4 H 0.4601 0.0581 0.6414 0.088 Uiso 1 1 calc R . .
C5 C 0.3851(3) 0.2012(3) 0.6013(3) 0.0620(10) Uani 1 1 d . . .
H5 H 0.4111 0.2391 0.6580 0.074 Uiso 1 1 calc R . .
C6 C 0.3153(2) 0.2506(3) 0.5248(2) 0.0510(9) Uani 1 1 d . . .
C7 C 0.2053(3) 0.3813(3) 0.4391(2) 0.0489(9) Uani 1 1 d . . .
C8 C 0.1543(3) 0.4813(3) 0.4205(2) 0.0513(9) Uani 1 1 d . . .
H8 H 0.1012 0.4901 0.3649 0.062 Uiso 1 1 calc R . .
C9 C 0.1808(2) 0.5689(3) 0.4833(2) 0.0448(8) Uani 1 1 d . . .
C10 C 0.1232(2) 0.6736(3) 0.45751(19) 0.0404(8) Uani 1 1 d . . .
C11 C 0.0135(3) 0.6700(3) 0.4242(2) 0.0498(9) Uani 1 1 d . . .
H11 H -0.0205 0.6024 0.4208 0.060 Uiso 1 1 calc R . .
C12 C -0.0457(3) 0.7628(3) 0.3964(2) 0.0507(9) Uani 1 1 d . . .
H12 H -0.1187 0.7567 0.3767 0.061 Uiso 1 1 calc R . .
C13 C 0.0008(3) 0.8658(3) 0.3970(2) 0.0488(9) Uani 1 1 d . . .
C14 C 0.1113(3) 0.8698(3) 0.4308(2) 0.0482(9) Uani 1 1 d . . .
H14 H 0.1456 0.9371 0.4329 0.058 Uiso 1 1 calc R . .
C15 C 0.1695(3) 0.7766(3) 0.4607(2) 0.0461(8) Uani 1 1 d . . .
H15 H 0.2422 0.7828 0.4838 0.055 Uiso 1 1 calc R . .
N3 N -0.0567(2) 0.9584(2) 0.3656(2) 0.0697(9) Uani 1 1 d . . .
C16 C -0.1698(3) 0.9591(3) 0.3518(2) 0.0689(11) Uani 1 1 d . . .
H16A H -0.2024 0.9229 0.2930 0.103 Uiso 1 1 calc R . .
H16B H -0.1943 1.0338 0.3496 0.103 Uiso 1 1 calc R . .
H16C H -0.1879 0.9212 0.4036 0.103 Uiso 1 1 calc R . .
C17 C -0.0065(3) 1.0624(3) 0.3589(3) 0.0689(11) Uani 1 1 d . . .
H17A H 0.0286 1.0875 0.4216 0.103 Uiso 1 1 calc R . .
H17B H -0.0587 1.1154 0.3291 0.103 Uiso 1 1 calc R . .
H17C H 0.0441 1.0538 0.3216 0.103 Uiso 1 1 calc R . .
C18 C 0.2925(2) 0.6485(3) 0.6277(2) 0.0446(8) Uani 1 1 d . . .
C19 C 0.2335(3) 0.6823(3) 0.6898(2) 0.0504(9) Uani 1 1 d . . .
C20 C 0.2720(3) 0.7693(3) 0.7514(2) 0.0639(10) Uani 1 1 d . . .
H20 H 0.2342 0.7932 0.7940 0.077 Uiso 1 1 calc R . .
C21 C 0.3653(3) 0.8197(3) 0.7495(3) 0.0717(12) Uani 1 1 d . . .
H21 H 0.3904 0.8773 0.7913 0.086 Uiso 1 1 calc R . .
C22 C 0.4213(3) 0.7862(3) 0.6870(3) 0.0664(11) Uani 1 1 d . . .
H22 H 0.4834 0.8226 0.6858 0.080 Uiso 1 1 calc R . .
C23 C 0.3875(3) 0.6989(3) 0.6250(2) 0.0532(9) Uani 1 1 d . . .
C25 C 0.4491(3) 0.6660(4) 0.5541(3) 0.0812(13) Uani 1 1 d . . .
H25A H 0.4797 0.7303 0.5334 0.122 Uiso 1 1 calc R . .
H25B H 0.4027 0.6312 0.5002 0.122 Uiso 1 1 calc R . .
H25C H 0.5041 0.6157 0.5836 0.122 Uiso 1 1 calc R . .
C24 C 0.1287(3) 0.6315(3) 0.6891(2) 0.0676(11) Uani 1 1 d . . .
H24A H 0.0793 0.6471 0.6295 0.101 Uiso 1 1 calc R . .
H24B H 0.1031 0.6616 0.7402 0.101 Uiso 1 1 calc R . .
H24C H 0.1368 0.5533 0.6971 0.101 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
S1 C1 1.737(3) . ?
S1 C7 1.738(3) . ?
B1 F1 1.367(4) . ?
B1 F2 1.407(5) . ?
B1 N2 1.543(4) . ?
B1 N1 1.549(5) . ?
N1 C7 1.342(3) . ?
N1 C6 1.407(4) . ?
N2 C9 1.351(3) . ?
N2 C18 1.450(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.388(4) . ?
C2 C3 1.365(5) . ?
C3 C4 1.380(5) . ?
C4 C5 1.383(5) . ?
C5 C6 1.386(4) . ?
C7 C8 1.381(4) . ?
C8 C9 1.388(4) . ?
C9 C10 1.479(4) . ?
C10 C15 1.387(4) . ?
C10 C11 1.396(4) . ?
C11 C12 1.370(4) . ?
C12 C13 1.392(4) . ?
C13 N3 1.367(4) . ?
C13 C14 1.407(4) . ?
C14 C15 1.374(4) . ?
N3 C17 1.440(4) . ?
N3 C16 1.444(4) . ?
C18 C19 1.387(4) . ?
C18 C23 1.396(4) . ?
C19 C20 1.395(4) . ?
C19 C24 1.502(4) . ?
C20 C21 1.373(5) . ?
C21 C22 1.363(5) . ?
C22 C23 1.390(5) . ?
C23 C25 1.512(5) . ?

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 S1 C7 90.73(16) . . ?
F1 B1 F2 108.2(3) . . ?
F1 B1 N2 111.8(3) . . ?
F2 B1 N2 109.9(3) . . ?
F1 B1 N1 110.0(3) . . ?
F2 B1 N1 108.2(3) . . ?
N2 B1 N1 108.6(3) . . ?
C7 N1 C6 112.9(3) . . ?
C7 N1 B1 121.4(3) . . ?
C6 N1 B1 125.7(3) . . ?
C9 N2 C18 120.8(3) . . ?
C9 N2 B1 123.7(3) . . ?
C18 N2 B1 115.1(2) . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 S1 128.2(3) . . ?
C6 C1 S1 110.6(3) . . ?
C3 C2 C1 118.0(4) . . ?
C2 C3 C4 121.3(4) . . ?
C3 C4 C5 121.3(4) . . ?
C4 C5 C6 117.8(4) . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 N1 126.5(3) . . ?
C1 C6 N1 113.0(3) . . ?
N1 C7 C8 123.1(3) . . ?
N1 C7 S1 112.7(3) . . ?
C8 C7 S1 124.2(2) . . ?
C7 C8 C9 121.2(3) . . ?
N2 C9 C8 119.6(3) . . ?
N2 C9 C10 122.6(3) . . ?
C8 C9 C10 117.8(3) . . ?
C15 C10 C11 116.3(3) . . ?
C15 C10 C9 125.2(3) . . ?
C11 C10 C9 118.4(3) . . ?
C12 C11 C10 122.2(3) . . ?
C11 C12 C13 121.6(3) . . ?
N3 C13 C12 122.3(3) . . ?
N3 C13 C14 121.4(3) . . ?
C12 C13 C14 116.3(3) . . ?
C15 C14 C13 121.5(3) . . ?
C14 C15 C10 122.0(3) . . ?
C13 N3 C17 121.5(3) . . ?
C13 N3 C16 120.8(3) . . ?
C17 N3 C16 117.1(3) . . ?
C19 C18 C23 122.3(3) . . ?
C19 C18 N2 119.4(3) . . ?
C23 C18 N2 118.3(3) . . ?
C18 C19 C20 117.9(3) . . ?
C18 C19 C24 122.0(3) . . ?
C20 C19 C24 120.0(3) . . ?
C21 C20 C19 120.5(4) . . ?
C22 C21 C20 120.6(4) . . ?
C21 C22 C23 121.4(4) . . ?
C22 C23 C18 117.3(3) . . ?
C22 C23 C25 120.3(4) . . ?
C18 C23 C25 122.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_Borebt6
_database_code_depnum_ccdc_archive 'CCDC 1029830'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 B F2 N4 S'
_chemical_formula_weight         462.36

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'
S S 0.1246 0.1234 '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'
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                   20.6963(13)
_cell_length_b                   8.5511(6)
_cell_length_c                   27.318(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.475(7)
_cell_angle_gamma                90.00
_cell_volume                     4636.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1299
_cell_measurement_theta_min      2.8590
_cell_measurement_theta_max      22.2420

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            9159
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4092
_reflns_number_gt                2403
_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)+(0.0390P)²+1.5673P] 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         4092
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
S1 S 0.39338(4) 1.04402(11) 0.42936(3) 0.0594(3) Uani 1 1 d . . .
B1 B 0.41307(16) 0.6714(4) 0.34161(12) 0.0410(8) Uani 1 1 d . . .
F1 F 0.41522(8) 0.7065(2) 0.29246(6) 0.0590(5) Uani 1 1 d . . .
F2 F 0.36566(8) 0.5549(2) 0.33898(6) 0.0578(5) Uani 1 1 d . . .
N1 N 0.39167(10) 0.8206(3) 0.36592(8) 0.0395(6) Uani 1 1 d . . .
N2 N 0.48250(10) 0.6188(3) 0.37538(8) 0.0393(6) Uani 1 1 d . . .
C1 C 0.32634(15) 1.0359(4) 0.37405(12) 0.0491(8) Uani 1 1 d . . .
C2 C 0.27174(17) 1.1368(4) 0.35917(14) 0.0646(10) Uani 1 1 d . . .
H2 H 0.2675 1.2223 0.3791 0.078 Uiso 1 1 calc R . .
C3 C 0.22441(17) 1.1052(5) 0.31395(16) 0.0712(11) Uani 1 1 d . . .
H3 H 0.1872 1.1708 0.3030 0.085 Uiso 1 1 calc R . .
C4 C 0.23024(15) 0.9791(5) 0.28418(13) 0.0640(10) Uani 1 1 d . . .
H4 H 0.1973 0.9623 0.2535 0.077 Uiso 1 1 calc R . .
C5 C 0.28442(14) 0.8762(4) 0.29907(11) 0.0493(8) Uani 1 1 d . . .
H5 H 0.2879 0.7898 0.2793 0.059 Uiso 1 1 calc R . .
C6 C 0.33303(13) 0.9082(4) 0.34463(11) 0.0437(8) Uani 1 1 d . . .
C7 C 0.42829(14) 0.8770(4) 0.41109(11) 0.0450(8) Uani 1 1 d . . .
C8 C 0.48798(14) 0.8103(4) 0.43895(11) 0.0500(8) Uani 1 1 d . . .
H8 H 0.5109 0.8525 0.4705 0.060 Uiso 1 1 calc R . .
C9 C 0.51440(13) 0.6808(4) 0.42067(10) 0.0418(7) Uani 1 1 d . . .
C10 C 0.57923(13) 0.6172(4) 0.45315(10) 0.0424(7) Uani 1 1 d . . .
C11 C 0.58544(14) 0.5797(4) 0.50371(11) 0.0498(8) Uani 1 1 d . . .
H11 H 0.5485 0.5944 0.5162 0.060 Uiso 1 1 calc R . .
C12 C 0.64378(15) 0.5219(4) 0.53599(11) 0.0590(9) Uani 1 1 d . . .
H12 H 0.6452 0.4968 0.5694 0.071 Uiso 1 1 calc R . .
C13 C 0.70133(15) 0.5001(4) 0.51953(12) 0.0584(9) Uani 1 1 d . . .
C14 C 0.69581(15) 0.5434(4) 0.46892(12) 0.0663(10) Uani 1 1 d . . .
H14 H 0.7334 0.5351 0.4568 0.080 Uiso 1 1 calc R . .
C15 C 0.63635(14) 0.5978(4) 0.43672(12) 0.0585(9) Uani 1 1 d . . .
H15 H 0.6344 0.6223 0.4031 0.070 Uiso 1 1 calc R . .
N3 N 0.75957(13) 0.4390(4) 0.55095(11) 0.0850(11) Uani 1 1 d . . .
C16 C 0.76057(18) 0.3718(6) 0.59885(14) 0.0955(15) Uani 1 1 d . . .
H16A H 0.7510 0.4511 0.6207 0.143 Uiso 1 1 calc R . .
H16B H 0.8042 0.3279 0.6145 0.143 Uiso 1 1 calc R . .
H16C H 0.7271 0.2909 0.5937 0.143 Uiso 1 1 calc R . .
C17 C 0.81889(16) 0.4257(6) 0.53362(15) 0.1001(16) Uani 1 1 d . . .
H17A H 0.8098 0.3572 0.5046 0.150 Uiso 1 1 calc R . .
H17B H 0.8552 0.3838 0.5606 0.150 Uiso 1 1 calc R . .
H17C H 0.8312 0.5271 0.5241 0.150 Uiso 1 1 calc R . .
C18 C 0.50858(13) 0.4793(3) 0.35755(10) 0.0381(7) Uani 1 1 d . . .
C19 C 0.49969(14) 0.3344(4) 0.37639(11) 0.0483(8) Uani 1 1 d . . .
H19 H 0.4771 0.3263 0.4013 0.058 Uiso 1 1 calc R . .
C20 C 0.52355(15) 0.2007(4) 0.35917(12) 0.0534(8) Uani 1 1 d . . .
H20 H 0.5172 0.1043 0.3728 0.064 Uiso 1 1 calc R . .
C21 C 0.55716(14) 0.2082(4) 0.32139(12) 0.0465(8) Uani 1 1 d . . .
C22 C 0.56502(14) 0.3554(4) 0.30254(12) 0.0514(8) Uani 1 1 d . . .
H22 H 0.5875 0.3651 0.2776 0.062 Uiso 1 1 calc R . .
C23 C 0.54037(14) 0.4878(4) 0.31986(11) 0.0498(8) Uani 1 1 d . . .
H23 H 0.5454 0.5845 0.3058 0.060 Uiso 1 1 calc R . .
N4 N 0.58061(14) 0.0757(3) 0.30354(12) 0.0663(8) Uani 1 1 d . . .
C24 C 0.5673(2) -0.0762(4) 0.31963(16) 0.0886(13) Uani 1 1 d . . .
H24A H 0.5937 -0.0928 0.3543 0.133 Uiso 1 1 calc R . .
H24B H 0.5788 -0.1533 0.2980 0.133 Uiso 1 1 calc R . .
H24C H 0.5203 -0.0848 0.3175 0.133 Uiso 1 1 calc R . .
C25 C 0.61685(17) 0.0865(4) 0.26559(14) 0.0765(11) Uani 1 1 d . . .
H25A H 0.5888 0.1355 0.2354 0.115 Uiso 1 1 calc R . .
H25B H 0.6290 -0.0165 0.2573 0.115 Uiso 1 1 calc R . .
H25C H 0.6569 0.1478 0.2788 0.115 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
S1 C7 1.736(3) . ?
S1 C1 1.739(3) . ?
B1 F2 1.385(4) . ?
B1 F1 1.389(3) . ?
B1 N2 1.538(4) . ?
B1 N1 1.559(4) . ?
N1 C7 1.341(3) . ?
N1 C6 1.404(3) . ?
N2 C9 1.336(3) . ?
N2 C18 1.449(3) . ?
C1 C6 1.386(4) . ?
C1 C2 1.388(4) . ?
C2 C3 1.368(5) . ?
C3 C4 1.376(5) . ?
C4 C5 1.392(4) . ?
C5 C6 1.388(4) . ?
C7 C8 1.378(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.486(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.388(4) . ?
C11 C12 1.370(4) . ?
C12 C13 1.400(4) . ?
C13 N3 1.369(4) . ?
C13 C14 1.404(4) . ?
C14 C15 1.375(4) . ?
N3 C16 1.424(4) . ?
N3 C17 1.440(4) . ?
C18 C23 1.372(3) . ?
C18 C19 1.374(4) . ?
C19 C20 1.380(4) . ?
C20 C21 1.400(4) . ?
C21 N4 1.375(4) . ?
C21 C22 1.387(4) . ?
C22 C23 1.380(4) . ?
N4 C24 1.423(4) . ?
N4 C25 1.444(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
C7 S1 C1 90.68(15) . . ?
F2 B1 F1 108.8(2) . . ?
F2 B1 N2 110.4(3) . . ?
F1 B1 N2 111.2(2) . . ?
F2 B1 N1 109.1(2) . . ?
F1 B1 N1 109.0(3) . . ?
N2 B1 N1 108.3(2) . . ?
C7 N1 C6 112.7(2) . . ?
C7 N1 B1 122.1(2) . . ?
C6 N1 B1 125.2(2) . . ?
C9 N2 C18 120.3(2) . . ?
C9 N2 B1 124.9(2) . . ?
C18 N2 B1 114.4(2) . . ?
C6 C1 C2 121.8(3) . . ?
C6 C1 S1 110.4(2) . . ?
C2 C1 S1 127.8(3) . . ?
C3 C2 C1 117.2(3) . . ?
C2 C3 C4 121.9(3) . . ?
C3 C4 C5 121.4(3) . . ?
C6 C5 C4 117.2(3) . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 N1 113.4(3) . . ?
C5 C6 N1 126.0(3) . . ?
N1 C7 C8 122.9(3) . . ?
N1 C7 S1 112.8(2) . . ?
C8 C7 S1 124.3(2) . . ?
C7 C8 C9 121.0(3) . . ?
N2 C9 C8 120.5(3) . . ?
N2 C9 C10 122.2(3) . . ?
C8 C9 C10 117.3(3) . . ?
C11 C10 C15 116.6(3) . . ?
C11 C10 C9 119.5(2) . . ?
C15 C10 C9 123.9(3) . . ?
C12 C11 C10 122.7(3) . . ?
C11 C12 C13 121.1(3) . . ?
N3 C13 C12 121.8(3) . . ?
N3 C13 C14 121.9(3) . . ?
C12 C13 C14 116.2(3) . . ?
C15 C14 C13 121.8(3) . . ?
C14 C15 C10 121.5(3) . . ?
C13 N3 C16 120.7(3) . . ?
C13 N3 C17 120.3(3) . . ?
C16 N3 C17 118.6(3) . . ?
C23 C18 C19 118.2(3) . . ?
C23 C18 N2 120.8(3) . . ?
C19 C18 N2 120.9(2) . . ?
C18 C19 C20 121.4(3) . . ?
C19 C20 C21 120.9(3) . . ?
N4 C21 C22 121.7(3) . . ?
N4 C21 C20 121.5(3) . . ?
C22 C21 C20 116.8(3) . . ?
C23 C22 C21 121.6(3) . . ?
C18 C23 C22 121.1(3) . . ?
C21 N4 C24 121.6(3) . . ?
C21 N4 C25 120.6(3) . . ?
C24 N4 C25 117.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.041
