# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_131030a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 B F2 N3 O'
_chemical_formula_weight         271.03

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'
O O 0.0106 0.0060 '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   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                   7.1363(8)
_cell_length_b                   8.4833(9)
_cell_length_c                   19.643(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.4140(10)
_cell_angle_gamma                90.00
_cell_volume                     1173.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5028
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9844
_exptl_absorpt_correction_T_max  0.9880
_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            9865
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.62
_reflns_number_total             2701
_reflns_number_gt                2190
_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)+(0.0596P)²+0.1492P] 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         2701
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.0219(2) 0.64187(17) 0.16937(7) 0.0416(3) Uani 1 1 d . . .
C1 C -0.18740(19) 0.80346(16) 0.07213(6) 0.0462(3) Uani 1 1 d . . .
C2 C -0.17225(18) 0.84134(15) -0.00083(6) 0.0444(3) Uani 1 1 d . . .
C3 C -0.2826(2) 0.93603(18) -0.04844(7) 0.0560(4) Uani 1 1 d . . .
H3 H -0.3880 0.9890 -0.0376 0.067 Uiso 1 1 calc R . .
C4 C -0.2303(2) 0.94920(18) -0.11307(7) 0.0593(4) Uani 1 1 d . . .
H4 H -0.3016 1.0127 -0.1462 0.071 Uiso 1 1 calc R . .
C5 C -0.0748(2) 0.87009(18) -0.12922(7) 0.0579(4) Uani 1 1 d . . .
H5 H -0.0441 0.8803 -0.1732 0.069 Uiso 1 1 calc R . .
C6 C 0.0367(2) 0.77580(16) -0.08127(7) 0.0512(3) Uani 1 1 d . . .
H6 H 0.1419 0.7226 -0.0921 0.061 Uiso 1 1 calc R . .
C7 C -0.01505(18) 0.76396(14) -0.01663(6) 0.0414(3) Uani 1 1 d . . .
C8 C 0.07425(17) 0.67898(14) 0.04561(6) 0.0386(3) Uani 1 1 d . . .
C9 C 0.29567(17) 0.52444(14) 0.11252(6) 0.0422(3) Uani 1 1 d . . .
C10 C 0.4620(2) 0.43649(18) 0.11790(8) 0.0560(4) Uani 1 1 d . . .
H10 H 0.5280 0.4317 0.0809 0.067 Uiso 1 1 calc R . .
C11 C 0.5284(2) 0.3571(2) 0.17762(8) 0.0609(4) Uani 1 1 d . . .
H11 H 0.6402 0.2991 0.1814 0.073 Uiso 1 1 calc R . .
C12 C 0.4288(2) 0.36332(18) 0.23227(8) 0.0568(4) Uani 1 1 d . . .
H12 H 0.4703 0.3073 0.2726 0.068 Uiso 1 1 calc R . .
C13 C 0.2689(2) 0.45286(15) 0.22598(6) 0.0486(3) Uani 1 1 d . . .
H13 H 0.2025 0.4585 0.2629 0.058 Uiso 1 1 calc R . .
F1 F 0.07683(13) 0.76118(10) 0.21591(4) 0.0619(3) Uani 1 1 d . . .
F2 F -0.11669(11) 0.55263(11) 0.19075(4) 0.0631(3) Uani 1 1 d . . .
N1 N -0.03383(15) 0.70327(12) 0.09628(5) 0.0414(2) Uani 1 1 d . . .
N2 N 0.22909(15) 0.59862(13) 0.05043(5) 0.0447(3) Uani 1 1 d . . .
N3 N 0.20315(14) 0.53419(12) 0.16743(5) 0.0404(2) Uani 1 1 d . . .
O1 O -0.30359(15) 0.84806(15) 0.10607(5) 0.0662(3) 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 1.3653(16) . ?
B1 F1 1.3771(16) . ?
B1 N1 1.5178(16) . ?
B1 N3 1.5888(18) . ?
C1 O1 1.2066(15) . ?
C1 N1 1.4066(17) . ?
C1 C2 1.4898(17) . ?
C2 C3 1.3782(19) . ?
C2 C7 1.3783(18) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3827(17) . ?
C6 H6 0.9300 . ?
C7 C8 1.4716(16) . ?
C8 N2 1.2886(16) . ?
C8 N1 1.3709(15) . ?
C9 N3 1.3561(16) . ?
C9 N2 1.3855(16) . ?
C9 C10 1.3912(19) . ?
C10 C11 1.369(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(2) . ?
C12 H12 0.9300 . ?
C13 N3 1.3573(16) . ?
C13 H13 0.9300 . ?

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 110.19(11) . . ?
F2 B1 N1 112.96(11) . . ?
F1 B1 N1 112.20(11) . . ?
F2 B1 N3 108.79(10) . . ?
F1 B1 N3 107.11(10) . . ?
N1 B1 N3 105.26(9) . . ?
O1 C1 N1 124.82(12) . . ?
O1 C1 C2 128.94(13) . . ?
N1 C1 C2 106.24(10) . . ?
C3 C2 C7 121.38(12) . . ?
C3 C2 C1 130.92(13) . . ?
C7 C2 C1 107.68(11) . . ?
C2 C3 C4 117.32(14) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.33(13) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 121.32(12) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 117.20(13) . . ?
C7 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
C2 C7 C6 121.44(12) . . ?
C2 C7 C8 107.70(10) . . ?
C6 C7 C8 130.85(12) . . ?
N2 C8 N1 127.14(11) . . ?
N2 C8 C7 124.74(10) . . ?
N1 C8 C7 108.12(10) . . ?
N3 C9 N2 122.07(11) . . ?
N3 C9 C10 119.51(12) . . ?
N2 C9 C10 118.42(12) . . ?
C11 C10 C9 120.05(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.78(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 118.79(13) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
N3 C13 C12 121.98(13) . . ?
N3 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C8 N1 C1 110.23(10) . . ?
C8 N1 B1 122.92(10) . . ?
C1 N1 B1 126.56(10) . . ?
C8 N2 C9 118.12(10) . . ?
C9 N3 C13 119.82(11) . . ?
C9 N3 B1 123.93(10) . . ?
C13 N3 B1 116.21(10) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 981350'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_131225d

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 B F2 N3 O S'
_chemical_formula_weight         383.22

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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                   8.5735(11)
_cell_length_b                   9.5948(12)
_cell_length_c                   13.8754(18)
_cell_angle_alpha                89.966(2)
_cell_angle_beta                 76.1290(10)
_cell_angle_gamma                63.7190(10)
_cell_volume                     986.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3418
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_T_max  0.9808
_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            8641
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         27.67
_reflns_number_total             4483
_reflns_number_gt                3206
_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)+(0.1500P)²+0.5000P] 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         4483
_refine_ls_number_parameters     278
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.2636
_refine_ls_wR_factor_gt          0.2499
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.013
_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 0.3072(5) 0.4574(5) 0.1079(3) 0.0514(8) Uani 1 1 d . . .
C1 C 0.5123(5) 0.2058(4) -0.0208(3) 0.0626(9) Uani 1 1 d . . .
C2 C 0.5166(5) 0.1549(4) -0.1228(3) 0.0604(9) Uani 1 1 d . . .
C3 C 0.6238(6) 0.0151(6) -0.1843(4) 0.0820(13) Uani 1 1 d . . .
H3 H 0.7143 -0.0684 -0.1649 0.098 Uiso 1 1 calc R . .
C4 C 0.5897(6) 0.0051(6) -0.2771(4) 0.0821(13) Uani 1 1 d . . .
H4 H 0.6598 -0.0869 -0.3209 0.098 Uiso 1 1 calc R . .
C5 C 0.4564(6) 0.1271(6) -0.3046(4) 0.0776(12) Uani 1 1 d . . .
H5 H 0.4373 0.1154 -0.3667 0.093 Uiso 1 1 calc R . .
C6 C 0.3485(6) 0.2670(5) -0.2442(3) 0.0672(10) Uani 1 1 d . . .
H6 H 0.2580 0.3496 -0.2642 0.081 Uiso 1 1 calc R . .
C7 C 0.3807(5) 0.2792(4) -0.1528(3) 0.0558(8) Uani 1 1 d . . .
C8 C 0.2911(4) 0.4065(4) -0.0694(3) 0.0500(7) Uani 1 1 d . . .
C9 C 0.1010(4) 0.6463(4) 0.0108(2) 0.0495(7) Uani 1 1 d . . .
C10 C -0.0557(4) 0.8826(4) 0.1310(2) 0.0494(7) Uani 1 1 d . . .
C11 C -0.1575(5) 1.0268(4) 0.1908(3) 0.0542(8) Uani 1 1 d . . .
H11 H -0.2434 1.1102 0.1686 0.065 Uiso 1 1 calc R . .
C12 C -0.1299(5) 1.0448(5) 0.2832(3) 0.0606(9) Uani 1 1 d . A .
C13 C 0.0028(6) 0.9132(5) 0.3125(3) 0.0682(10) Uani 1 1 d . . .
H13 H 0.0229 0.9244 0.3743 0.082 Uiso 1 1 calc R . .
C14 C 0.1039(6) 0.7695(5) 0.2552(3) 0.0655(10) Uani 1 1 d . . .
H14 H 0.1890 0.6855 0.2775 0.079 Uiso 1 1 calc R . .
C15 C 0.0729(4) 0.7556(4) 0.1621(2) 0.0496(7) Uani 1 1 d . . .
C16 C -0.2344(5) 1.1993(5) 0.3508(3) 0.0704(10) Uani 1 1 d D . .
C17 C -0.3896(11) 1.3206(9) 0.3110(7) 0.082(2) Uani 0.645(11) 1 d PDU A 1
H17A H -0.3396 1.3552 0.2520 0.123 Uiso 0.645(11) 1 calc PR A 1
H17B H -0.4660 1.4086 0.3613 0.123 Uiso 0.645(11) 1 calc PR A 1
H17C H -0.4593 1.2729 0.2950 0.123 Uiso 0.645(11) 1 calc PR A 1
C18 C -0.1050(12) 1.2656(14) 0.3590(13) 0.123(5) Uani 0.645(11) 1 d PDU A 1
H18A H -0.0530 1.2841 0.2940 0.184 Uiso 0.645(11) 1 calc PR A 1
H18B H -0.0109 1.1921 0.3854 0.184 Uiso 0.645(11) 1 calc PR A 1
H18C H -0.1699 1.3624 0.4028 0.184 Uiso 0.645(11) 1 calc PR A 1
C19 C -0.3215(17) 1.1749(13) 0.4543(6) 0.114(4) Uani 0.645(11) 1 d PDU A 1
H19A H -0.3626 1.0980 0.4481 0.172 Uiso 0.645(11) 1 calc PR A 1
H19B H -0.4221 1.2720 0.4873 0.172 Uiso 0.645(11) 1 calc PR A 1
H19C H -0.2346 1.1393 0.4928 0.172 Uiso 0.645(11) 1 calc PR A 1
C17' C -0.4376(11) 1.265(2) 0.3691(16) 0.119(7) Uani 0.355(11) 1 d PDU A 2
H17D H -0.4839 1.3641 0.3428 0.178 Uiso 0.355(11) 1 calc PR A 2
H17E H -0.4931 1.2806 0.4396 0.178 Uiso 0.355(11) 1 calc PR A 2
H17F H -0.4642 1.1937 0.3364 0.178 Uiso 0.355(11) 1 calc PR A 2
C18' C -0.167(3) 1.314(2) 0.3036(15) 0.123(7) Uani 0.355(11) 1 d PDU A 2
H18D H -0.0493 1.2864 0.3119 0.184 Uiso 0.355(11) 1 calc PR A 2
H18E H -0.2490 1.4187 0.3358 0.184 Uiso 0.355(11) 1 calc PR A 2
H18F H -0.1612 1.3102 0.2336 0.184 Uiso 0.355(11) 1 calc PR A 2
C19' C -0.198(2) 1.1858(19) 0.4559(8) 0.097(5) Uani 0.355(11) 1 d PDU A 2
H19D H -0.1764 1.0838 0.4745 0.145 Uiso 0.355(11) 1 calc PR A 2
H19E H -0.3007 1.2642 0.5041 0.145 Uiso 0.355(11) 1 calc PR A 2
H19F H -0.0937 1.2010 0.4538 0.145 Uiso 0.355(11) 1 calc PR A 2
F1 F 0.4456(3) 0.4762(3) 0.12985(19) 0.0723(7) Uani 1 1 d . . .
F2 F 0.2292(3) 0.3989(3) 0.18450(17) 0.0686(6) Uani 1 1 d . . .
N1 N 0.3682(4) 0.3568(3) 0.0064(2) 0.0530(7) Uani 1 1 d . . .
N2 N 0.1579(4) 0.5423(3) -0.0714(2) 0.0525(7) Uani 1 1 d . . .
N3 N 0.1596(4) 0.6212(3) 0.0919(2) 0.0480(6) Uani 1 1 d . . .
O1 O 0.6100(4) 0.1363(4) 0.0307(3) 0.0879(10) Uani 1 1 d . . .
S1 S -0.06418(11) 0.83299(10) 0.01274(6) 0.0520(3) 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 1.372(4) . ?
B1 F1 1.377(4) . ?
B1 N1 1.546(5) . ?
B1 N3 1.578(4) . ?
C1 O1 1.203(5) . ?
C1 N1 1.400(5) . ?
C1 C2 1.485(6) . ?
C2 C3 1.380(6) . ?
C2 C7 1.398(5) . ?
C3 C4 1.400(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.471(5) . ?
C8 N2 1.304(4) . ?
C8 N1 1.351(4) . ?
C9 N3 1.320(4) . ?
C9 N2 1.356(4) . ?
C9 S1 1.718(3) . ?
C10 C15 1.386(5) . ?
C10 C11 1.396(5) . ?
C10 S1 1.736(3) . ?
C11 C12 1.382(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.415(6) . ?
C12 C16 1.518(6) . ?
C13 C14 1.377(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.399(5) . ?
C14 H14 0.9300 . ?
C15 N3 1.403(4) . ?
C16 C17' 1.520(8) . ?
C16 C19 1.521(6) . ?
C16 C18 1.528(7) . ?
C16 C18' 1.538(8) . ?
C16 C17 1.553(6) . ?
C16 C19' 1.557(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?
C19' H19D 0.9600 . ?
C19' H19E 0.9600 . ?
C19' H19F 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 110.6(3) . . ?
F2 B1 N1 111.9(3) . . ?
F1 B1 N1 112.4(3) . . ?
F2 B1 N3 109.1(3) . . ?
F1 B1 N3 109.2(3) . . ?
N1 B1 N3 103.4(3) . . ?
O1 C1 N1 125.0(4) . . ?
O1 C1 C2 129.0(4) . . ?
N1 C1 C2 106.0(3) . . ?
C3 C2 C7 121.0(4) . . ?
C3 C2 C1 131.5(4) . . ?
C7 C2 C1 107.5(3) . . ?
C2 C3 C4 116.8(5) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 122.6(5) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C7 116.9(4) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
C6 C7 C2 121.5(4) . . ?
C6 C7 C8 131.8(4) . . ?
C2 C7 C8 106.7(3) . . ?
N2 C8 N1 127.6(3) . . ?
N2 C8 C7 123.8(3) . . ?
N1 C8 C7 108.7(3) . . ?
N3 C9 N2 127.1(3) . . ?
N3 C9 S1 114.5(3) . . ?
N2 C9 S1 118.3(3) . . ?
C15 C10 C11 121.7(3) . . ?
C15 C10 S1 110.4(3) . . ?
C11 C10 S1 127.9(3) . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 117.4(3) . . ?
C11 C12 C16 122.0(4) . . ?
C13 C12 C16 120.6(3) . . ?
C14 C13 C12 124.1(4) . . ?
C14 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
C13 C14 C15 117.0(4) . . ?
C13 C14 H14 121.5 . . ?
C15 C14 H14 121.5 . . ?
C10 C15 C14 120.2(3) . . ?
C10 C15 N3 113.1(3) . . ?
C14 C15 N3 126.7(3) . . ?
C12 C16 C17' 113.0(8) . . ?
C12 C16 C19 110.2(5) . . ?
C17' C16 C19 68.7(10) . . ?
C12 C16 C18 109.1(5) . . ?
C17' C16 C18 135.5(10) . . ?
C19 C16 C18 109.5(8) . . ?
C12 C16 C18' 107.9(8) . . ?
C17' C16 C18' 111.3(10) . . ?
C19 C16 C18' 138.0(10) . . ?
C18 C16 C18' 39.4(7) . . ?
C12 C16 C17 112.0(4) . . ?
C17' C16 C17 40.5(8) . . ?
C19 C16 C17 106.7(6) . . ?
C18 C16 C17 109.3(7) . . ?
C18' C16 C17 74.0(11) . . ?
C12 C16 C19' 112.7(7) . . ?
C17' C16 C19' 106.2(8) . . ?
C19 C16 C19' 42.5(6) . . ?
C18 C16 C19' 69.0(9) . . ?
C18' C16 C19' 105.6(10) . . ?
C17 C16 C19' 132.8(8) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
C16 C17' H17D 109.5 . . ?
C16 C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C16 C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C16 C18' H18D 109.5 . . ?
C16 C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C16 C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C16 C19' H19D 109.5 . . ?
C16 C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C16 C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C8 N1 C1 111.0(3) . . ?
C8 N1 B1 123.8(3) . . ?
C1 N1 B1 125.2(3) . . ?
C8 N2 C9 114.4(3) . . ?
C9 N3 C15 112.0(3) . . ?
C9 N3 B1 123.4(3) . . ?
C15 N3 B1 124.6(3) . . ?
C9 S1 C10 89.95(16) . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.017 0.480 0.500 177 48 ' '
_platon_squeeze_details          
;
;
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.67
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 981351'
