# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_150106a_0m
_audit_block_doi                 10.5517/cc1jq2y8
_database_code_depnum_ccdc_archive 'CCDC 1421410'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        4
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H34 B2 F4 N4'
_chemical_formula_weight         536.22

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'
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                   26.145(4)
_cell_length_b                   7.6970(12)
_cell_length_c                   14.341(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.917(2)
_cell_angle_gamma                90.00
_cell_volume                     2823.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4314
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            11814
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         27.59
_reflns_number_total             3260
_reflns_number_gt                2360
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0828P)²+3.8667P] 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     SHELXL
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1978
_refine_ls_wR_factor_gt          0.1807
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.014
_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 0.41498(12) 1.0688(4) 0.21822(18) 0.0559(7) Uani 1 1 d . . .
C1 C 0.48193(8) 1.2854(3) 0.32618(15) 0.0449(5) Uani 1 1 d . . .
C2 C 0.49751(10) 1.3151(3) 0.42423(17) 0.0567(6) Uani 1 1 d . . .
H2 H 0.5213 1.3989 0.4529 0.068 Uiso 1 1 calc R . .
C3 C 0.47187(10) 1.1999(3) 0.47055(16) 0.0572(6) Uani 1 1 d . . .
H3 H 0.4748 1.1912 0.5361 0.069 Uiso 1 1 calc R . .
C4 C 0.44039(8) 1.0976(3) 0.40122(14) 0.0465(5) Uani 1 1 d . . .
C5 C 0.41090(9) 0.9533(3) 0.41367(15) 0.0511(5) Uani 1 1 d . . .
H5 H 0.4101 0.9177 0.4753 0.061 Uiso 1 1 calc R . .
C6 C 0.38296(9) 0.8610(3) 0.33866(15) 0.0494(5) Uani 1 1 d . . .
C7 C 0.35111(11) 0.7114(3) 0.3348(2) 0.0643(7) Uani 1 1 d . . .
C8 C 0.33079(11) 0.6791(4) 0.2408(2) 0.0699(7) Uani 1 1 d . . .
C9 C 0.35027(10) 0.8094(3) 0.18740(18) 0.0608(6) Uani 1 1 d . . .
C10 C 0.33874(14) 0.8301(5) 0.0820(2) 0.0921(11) Uani 1 1 d . . .
H10A H 0.3193 0.9352 0.0650 0.138 Uiso 1 1 calc R . .
H10B H 0.3186 0.7327 0.0530 0.138 Uiso 1 1 calc R . .
H10C H 0.3709 0.8358 0.0598 0.138 Uiso 1 1 calc R . .
C11 C 0.29511(15) 0.5329(5) 0.1973(3) 0.1016(12) Uani 1 1 d . . .
H11A H 0.3033 0.4999 0.1367 0.122 Uiso 1 1 calc R . .
H11B H 0.3009 0.4326 0.2391 0.122 Uiso 1 1 calc R . .
C12 C 0.24010(17) 0.5854(7) 0.1824(4) 0.151(2) Uani 1 1 d . . .
H12A H 0.2310 0.6058 0.2430 0.227 Uiso 1 1 calc R . .
H12B H 0.2184 0.4949 0.1494 0.227 Uiso 1 1 calc R . .
H12C H 0.2349 0.6900 0.1452 0.227 Uiso 1 1 calc R . .
C13 C 0.34306(16) 0.6093(5) 0.4200(3) 0.1028(12) Uani 1 1 d . . .
H13A H 0.3553 0.4926 0.4157 0.154 Uiso 1 1 calc R . .
H13B H 0.3065 0.6073 0.4214 0.154 Uiso 1 1 calc R . .
H13C H 0.3622 0.6628 0.4771 0.154 Uiso 1 1 calc R . .
C14 C 0.5000 1.3915(4) 0.2500 0.0519(8) Uani 1 2 d S . .
C15 C 0.45414(12) 1.5116(3) 0.2048(2) 0.0751(8) Uani 1 1 d . . .
H15A H 0.4654 1.5897 0.1609 0.113 Uiso 1 1 calc R . .
H15B H 0.4430 1.5771 0.2540 0.113 Uiso 1 1 calc R . .
H15C H 0.4256 1.4424 0.1715 0.113 Uiso 1 1 calc R . .
F1 F 0.44765(8) 1.0003(3) 0.16483(13) 0.1130(9) Uani 1 1 d . . .
F2 F 0.38262(10) 1.1856(3) 0.16512(15) 0.1307(10) Uani 1 1 d . . .
N1 N 0.44614(6) 1.1541(2) 0.31132(11) 0.0417(4) Uani 1 1 d . . .
N2 N 0.38186(7) 0.9174(2) 0.24605(12) 0.0471(5) 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 F2 1.356(3) . ?
B1 F1 1.365(3) . ?
B1 N1 1.558(3) . ?
B1 N2 1.552(3) . ?
C1 N1 1.364(3) . ?
C1 C2 1.400(3) . ?
C1 C14 1.516(3) . ?
C2 C3 1.364(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 N1 1.398(3) . ?
C5 C6 1.368(3) . ?
C5 H5 0.9300 . ?
C6 N2 1.392(3) . ?
C6 C7 1.416(3) . ?
C7 C8 1.366(4) . ?
C7 C13 1.502(4) . ?
C8 C9 1.419(4) . ?
C8 C11 1.512(4) . ?
C9 N2 1.339(3) . ?
C9 C10 1.488(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.467(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C1 1.516(3) 2_655 ?
C14 C15 1.546(3) 2_655 ?
C14 C15 1.546(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
F2 B1 F1 109.3(2) . . ?
F2 B1 N1 110.9(2) . . ?
F1 B1 N1 111.5(2) . . ?
F2 B1 N2 109.0(2) . . ?
F1 B1 N2 107.5(2) . . ?
N1 B1 N2 108.46(17) . . ?
N1 C1 C2 109.03(19) . . ?
N1 C1 C14 126.36(18) . . ?
C2 C1 C14 124.51(19) . . ?
C3 C2 C1 108.2(2) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
C2 C3 C4 107.3(2) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C5 C4 N1 122.49(19) . . ?
C5 C4 C3 128.5(2) . . ?
N1 C4 C3 108.8(2) . . ?
C6 C5 C4 122.4(2) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 N2 119.4(2) . . ?
C5 C6 C7 131.8(2) . . ?
N2 C6 C7 108.7(2) . . ?
C8 C7 C6 107.0(2) . . ?
C8 C7 C13 128.0(3) . . ?
C6 C7 C13 125.0(3) . . ?
C7 C8 C9 107.1(2) . . ?
C7 C8 C11 128.6(3) . . ?
C9 C8 C11 124.3(3) . . ?
N2 C9 C8 110.1(2) . . ?
N2 C9 C10 122.8(2) . . ?
C8 C9 C10 127.2(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 111.0(4) . . ?
C12 C11 H11A 109.4 . . ?
C8 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C8 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 C1 114.8(2) 2_655 . ?
C1 C14 C15 107.10(13) 2_655 2_655 ?
C1 C14 C15 110.50(14) . 2_655 ?
C1 C14 C15 110.50(14) 2_655 . ?
C1 C14 C15 107.10(13) . . ?
C15 C14 C15 106.6(3) 2_655 . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 C4 106.69(17) . . ?
C1 N1 B1 131.79(18) . . ?
C4 N1 B1 121.51(17) . . ?
C9 N2 C6 107.13(19) . . ?
C9 N2 B1 127.50(19) . . ?
C6 N2 B1 125.21(18) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.048
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_150714a
_audit_block_doi                 10.5517/cc1jq2z9
_database_code_depnum_ccdc_archive 'CCDC 1421411'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H32 B2 F4 N4'
_chemical_formula_weight         534.21

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           Orthorhombic
_symmetry_space_group_name_H-M   Cmc2(1)

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

_cell_length_a                   23.035(2)
_cell_length_b                   17.8506(18)
_cell_length_c                   7.0291(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2890.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4819
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      24.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            12202
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3306
_reflns_number_gt                2665
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.2000P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0037(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(15)
_refine_ls_number_reflns         3306
_refine_ls_number_parameters     199
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.2500
_refine_ls_wR_factor_gt          0.2346
_refine_ls_goodness_of_fit_ref   1.024
_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
B1 B 0.35267(19) 0.3468(2) 0.5826(5) 0.0479(8) Uani 1 1 d . . .
C1 C 0.45062(14) 0.37755(16) 0.4084(4) 0.0417(7) Uani 1 1 d . . .
C2 C 0.46837(14) 0.41534(17) 0.2426(5) 0.0419(7) Uani 1 1 d . . .
C3 C 0.41934(14) 0.43988(18) 0.1490(5) 0.0454(7) Uani 1 1 d . . .
H3 H 0.4178 0.4664 0.0351 0.054 Uiso 1 1 calc R . .
C4 C 0.37202(15) 0.41664(16) 0.2610(5) 0.0440(7) Uani 1 1 d . . .
C5 C 0.31249(16) 0.42672(18) 0.2335(5) 0.0477(7) Uani 1 1 d . . .
H5 H 0.3000 0.4520 0.1254 0.057 Uiso 1 1 calc R . .
C6 C 0.27153(15) 0.40074(18) 0.3602(5) 0.0496(8) Uani 1 1 d . . .
C7 C 0.20992(15) 0.4037(2) 0.3601(6) 0.0553(9) Uani 1 1 d . . .
C8 C 0.19090(17) 0.36989(19) 0.5249(7) 0.0552(9) Uani 1 1 d . . .
C9 C 0.24122(15) 0.34525(19) 0.6251(6) 0.0510(8) Uani 1 1 d . . .
C10 C 0.17381(19) 0.4354(3) 0.2044(8) 0.0780(14) Uani 1 1 d . . .
H10A H 0.1563 0.3954 0.1336 0.117 Uiso 1 1 calc R . .
H10B H 0.1978 0.4648 0.1213 0.117 Uiso 1 1 calc R . .
H10C H 0.1440 0.4666 0.2577 0.117 Uiso 1 1 calc R . .
C11 C 0.13085(18) 0.3602(3) 0.5940(9) 0.0722(12) Uani 1 1 d . . .
H11A H 0.1069 0.3995 0.5398 0.087 Uiso 1 1 calc R . .
H11B H 0.1306 0.3666 0.7311 0.087 Uiso 1 1 calc R . .
C12 C 0.1037(3) 0.2851(4) 0.5465(11) 0.0986(19) Uani 1 1 d . . .
H12A H 0.1028 0.2786 0.4109 0.148 Uiso 1 1 calc R . .
H12B H 0.0649 0.2833 0.5958 0.148 Uiso 1 1 calc R . .
H12C H 0.1264 0.2457 0.6026 0.148 Uiso 1 1 calc R . .
C13 C 0.2445(2) 0.3041(3) 0.8089(7) 0.0673(11) Uani 1 1 d . . .
H13A H 0.2559 0.2532 0.7857 0.101 Uiso 1 1 calc R . .
H13B H 0.2072 0.3048 0.8695 0.101 Uiso 1 1 calc R . .
H13C H 0.2725 0.3278 0.8901 0.101 Uiso 1 1 calc R . .
C14 C 0.5000 0.3451(2) 0.5267(6) 0.0408(9) Uani 1 2 d S . .
C15 C 0.5000 0.2587(3) 0.5136(10) 0.0567(12) Uani 1 2 d SD . .
C16 C 0.5000 0.3692(3) 0.7353(8) 0.0558(12) Uani 1 2 d SD . .
F1 F 0.36083(9) 0.27007(12) 0.5969(4) 0.0648(6) Uani 1 1 d . . .
F2 F 0.36504(11) 0.38021(15) 0.7529(3) 0.0734(8) Uani 1 1 d . . .
N1 N 0.39246(12) 0.37837(13) 0.4231(4) 0.0413(6) Uani 1 1 d . . .
N2 N 0.28941(13) 0.36335(15) 0.5261(4) 0.0463(6) Uani 1 1 d . . .
H15A H 0.5000 0.244(3) 0.381(4) 0.059(16) Uiso 1 2 d SD . .
H15B H 0.4750(18) 0.237(3) 0.605(7) 0.083(15) Uiso 1 1 d D . .
H16B H 0.4668(13) 0.352(2) 0.807(6) 0.052(10) Uiso 1 1 d D . .
H16A H 0.5000 0.4227(15) 0.75(3) 0.18(5) Uiso 1 2 d SD . .


_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 1.367(5) . ?
B1 F1 1.387(4) . ?
B1 N2 1.539(5) . ?
B1 N1 1.554(5) . ?
C1 N1 1.344(4) . ?
C1 C2 1.408(4) . ?
C1 C14 1.523(4) . ?
C2 C3 1.378(5) . ?
C2 C2 1.457(6) 4_655 ?
C3 C4 1.407(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(5) . ?
C4 N1 1.410(4) . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.406(5) . ?
C6 C7 1.420(5) . ?
C7 C8 1.378(6) . ?
C7 C10 1.487(6) . ?
C8 C9 1.426(6) . ?
C8 C11 1.476(6) . ?
C9 N2 1.349(5) . ?
C9 C13 1.488(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.518(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C1 1.523(4) 4_655 ?
C14 C16 1.528(7) . ?
C14 C15 1.545(6) . ?
C15 H15A 0.97(2) . ?
C15 H15B 0.95(2) . ?
C16 H16B 0.967(19) . ?
C16 H16A 0.96(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 B1 F1 109.8(3) . . ?
F2 B1 N2 109.8(3) . . ?
F1 B1 N2 109.7(3) . . ?
F2 B1 N1 110.5(3) . . ?
F1 B1 N1 109.3(3) . . ?
N2 B1 N1 107.6(3) . . ?
N1 C1 C2 110.4(3) . . ?
N1 C1 C14 135.0(3) . . ?
C2 C1 C14 114.7(3) . . ?
C3 C2 C1 108.0(3) . . ?
C3 C2 C2 145.02(19) . 4_655 ?
C1 C2 C2 106.89(19) . 4_655 ?
C2 C3 C4 105.9(3) . . ?
C2 C3 H3 127.1 . . ?
C4 C3 H3 127.1 . . ?
C3 C4 C5 130.2(3) . . ?
C3 C4 N1 109.7(3) . . ?
C5 C4 N1 120.1(3) . . ?
C6 C5 C4 122.7(3) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 N2 119.7(3) . . ?
C5 C6 C7 132.2(3) . . ?
N2 C6 C7 108.1(3) . . ?
C8 C7 C6 107.5(3) . . ?
C8 C7 C10 127.4(4) . . ?
C6 C7 C10 125.0(3) . . ?
C7 C8 C9 107.0(3) . . ?
C7 C8 C11 128.7(4) . . ?
C9 C8 C11 124.3(4) . . ?
N2 C9 C8 109.9(3) . . ?
N2 C9 C13 121.6(3) . . ?
C8 C9 C13 128.5(4) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 C12 114.6(4) . . ?
C8 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C8 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 C1 96.6(3) . 4_655 ?
C1 C14 C16 114.6(2) . . ?
C1 C14 C16 114.6(2) 4_655 . ?
C1 C14 C15 110.3(3) . . ?
C1 C14 C15 110.3(3) 4_655 . ?
C16 C14 C15 109.8(4) . . ?
C14 C15 H15A 109(4) . . ?
C14 C15 H15B 112(3) . . ?
H15A C15 H15B 123(4) . . ?
C14 C16 H16B 114(3) . . ?
C14 C16 H16A 111(10) . . ?
H16B C16 H16A 107(8) . . ?
C1 N1 C4 106.0(3) . . ?
C1 N1 B1 129.8(3) . . ?
C4 N1 B1 124.2(3) . . ?
C9 N2 C6 107.5(3) . . ?
C9 N2 B1 126.9(3) . . ?
C6 N2 B1 125.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.050
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.103
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       Luminescent
