# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

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

data_z
_database_code_depnum_ccdc_archive 'CCDC 1578828'
_audit_update_record             
;
2017-10-09 deposited with the CCDC.
2017-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 B F2 N2 S4'
_chemical_formula_sum            'C23 H15 B F2 N2 S4'
_chemical_formula_weight         496.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   10.9246(6)
_cell_length_b                   11.2207(7)
_cell_length_c                   18.6557(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.4020(10)
_cell_angle_gamma                90
_cell_volume                     2286.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3350
_cell_measurement_theta_min      2.183
_cell_measurement_theta_max      30.002

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            DARK-RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   0.842
_exptl_transmission_factor_max   0.916
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.446
_shelx_estimated_absorpt_T_min   0.842
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12448
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.183
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3040
_reflns_number_gt                2328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0784P)²+2.1642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3040
_refine_ls_number_parameters     160
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.113
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.5000 0.0050(3) 0.2500 0.0310(6) Uani 1 2 d S T P . .
F1 F 0.41212(11) -0.06598(11) 0.28169(7) 0.0406(3) Uani 1 1 d . . . . .
S1 S 0.63471(6) -0.09771(5) 0.38787(3) 0.0492(2) Uani 1 1 d . . . . .
S11 S 0.8681(2) -0.0861(2) 0.47328(12) 0.0533(6) Uani 0.577(4) 1 d . . P A 1
C11 C 0.6624(12) -0.0968(6) 0.5340(5) 0.0724(8) Uani 0.577(4) 1 d D . P A 1
H11A H 0.5773 -0.1072 0.5420 0.087 Uiso 0.577(4) 1 calc R U P A 1
S21 S 0.6518(3) -0.0601(2) 0.54580(13) 0.0724(8) Uani 0.423(4) 1 d D . P A 2
C21 C 0.8468(15) -0.1178(9) 0.4794(7) 0.059(4) Uani 0.423(4) 1 d D . P A 2
H21A H 0.9051 -0.1438 0.4452 0.071 Uiso 0.423(4) 1 calc R U P A 2
N1 N 0.56030(16) 0.08740(13) 0.30678(9) 0.0331(4) Uani 1 1 d . . . . .
C1 C 0.5000 0.6533(3) 0.2500 0.0528(9) Uani 1 2 d S T P . .
H1A H 0.5000 0.7379 0.2500 0.063 Uiso 1 2 calc R U P . .
C2 C 0.6066(3) 0.5917(2) 0.23819(15) 0.0520(6) Uani 1 1 d . . . . .
H2A H 0.6801 0.6341 0.2291 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6078(2) 0.46825(18) 0.23951(13) 0.0434(5) Uani 1 1 d . . . . .
H3A H 0.6825 0.4264 0.2332 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5000 0.4057(2) 0.2500 0.0308(5) Uani 1 2 d S T P . .
C5 C 0.5000 0.2737(2) 0.2500 0.0303(5) Uani 1 2 d S T P . .
C6 C 0.56108(18) 0.21194(15) 0.30445(10) 0.0325(4) Uani 1 1 d . . . . .
C7 C 0.6258(2) 0.25323(17) 0.36532(11) 0.0392(5) Uani 1 1 d . . . . .
H7A H 0.6406 0.3342 0.3775 0.047 Uiso 1 1 calc R U . . .
C8 C 0.6637(2) 0.15490(18) 0.40398(12) 0.0445(5) Uani 1 1 d . . . . .
H8A H 0.7095 0.1554 0.4474 0.053 Uiso 1 1 calc R U . . .
C9 C 0.6211(2) 0.05349(17) 0.36655(11) 0.0388(5) Uani 1 1 d . . . . .
C10 C 0.7167(2) -0.08980(17) 0.46830(12) 0.0405(5) Uani 1 1 d D . . . .
C12 C 0.7588(4) -0.0854(3) 0.59184(17) 0.0741(9) Uani 1 1 d D . . . .
H12B H 0.7434 -0.0740 0.6414 0.089 Uiso 0.577(4) 1 calc R U P A 1
H12A H 0.7493 -0.0955 0.6421 0.089 Uiso 0.423(4) 1 calc R U P A 2
C13 C 0.8659(3) -0.0938(2) 0.56306(18) 0.0660(8) Uani 1 1 d D . . . .
H13B H 0.9384 -0.1037 0.5909 0.079 Uiso 0.577(4) 1 calc R U P A 1
H13A H 0.9423 -0.0869 0.5874 0.079 Uiso 0.423(4) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.383(2) . ?
B1 F1 1.383(2) 2_655 ?
B1 N1 1.550(2) . ?
B1 N1 1.550(2) 2_655 ?
S1 C10 1.744(2) . ?
S1 C9 1.749(2) . ?
S11 C10 1.657(3) . ?
S11 C13 1.677(4) . ?
C11 C10 1.368(10) . ?
C11 C12 1.508(11) . ?
C11 H11A 0.9500 . ?
S21 C12 1.474(5) . ?
S21 C10 1.649(3) . ?
C21 C10 1.470(16) . ?
C21 C13 1.596(14) . ?
C21 H21A 0.9500 . ?
N1 C9 1.349(2) . ?
N1 C6 1.398(2) . ?
C1 C2 1.373(3) 2_655 ?
C1 C2 1.373(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3A 0.9500 . ?
C4 C3 1.386(2) 2_655 ?
C4 C5 1.481(3) . ?
C5 C6 1.396(2) 2_655 ?
C5 C6 1.396(2) . ?
C6 C7 1.412(3) . ?
C7 C8 1.380(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.412(3) . ?
C8 H8A 0.9500 . ?
C12 C13 1.294(5) . ?
C12 H12B 0.9500 . ?
C12 H12A 0.9500 . ?
C13 H13B 0.9500 . ?
C13 H13A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F1 109.7(2) . 2_655 ?
F1 B1 N1 110.14(8) . . ?
F1 B1 N1 110.04(8) 2_655 . ?
F1 B1 N1 110.04(8) . 2_655 ?
F1 B1 N1 110.14(8) 2_655 2_655 ?
N1 B1 N1 106.7(2) . 2_655 ?
C10 S1 C9 100.87(9) . . ?
C10 S11 C13 91.92(19) . . ?
C10 C11 C12 109.3(8) . . ?
C10 C11 H11A 125.3 . . ?
C12 C11 H11A 125.3 . . ?
C12 S21 C10 97.3(2) . . ?
C10 C21 C13 102.8(10) . . ?
C10 C21 H21A 128.6 . . ?
C13 C21 H21A 128.6 . . ?
C9 N1 C6 107.73(16) . . ?
C9 N1 B1 126.95(16) . . ?
C6 N1 B1 125.32(16) . . ?
C2 C1 C2 119.6(3) 2_655 . ?
C2 C1 H1A 120.2 2_655 . ?
C2 C1 H1A 120.2 . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C3 119.1(3) 2_655 . ?
C3 C4 C5 120.43(13) 2_655 . ?
C3 C4 C5 120.42(13) . . ?
C6 C5 C6 120.4(2) 2_655 . ?
C6 C5 C4 119.78(12) 2_655 . ?
C6 C5 C4 119.78(12) . . ?
C5 C6 N1 121.06(18) . . ?
C5 C6 C7 131.05(18) . . ?
N1 C6 C7 107.83(16) . . ?
C8 C7 C6 107.74(17) . . ?
C8 C7 H7A 126.1 . . ?
C6 C7 H7A 126.1 . . ?
C7 C8 C9 106.83(18) . . ?
C7 C8 H8A 126.6 . . ?
C9 C8 H8A 126.6 . . ?
N1 C9 C8 109.87(17) . . ?
N1 C9 S1 120.16(15) . . ?
C8 C9 S1 129.96(16) . . ?
C21 C10 S21 110.0(6) . . ?
C11 C10 S11 113.0(5) . . ?
C11 C10 S1 123.0(5) . . ?
C21 C10 S1 126.9(6) . . ?
S21 C10 S1 122.91(19) . . ?
S11 C10 S1 123.77(16) . . ?
C13 C12 S21 119.2(3) . . ?
C13 C12 C11 109.0(5) . . ?
C13 C12 H12B 125.5 . . ?
C11 C12 H12B 125.5 . . ?
C13 C12 H12A 120.4 . . ?
S21 C12 H12A 120.4 . . ?
C12 C13 C21 107.8(6) . . ?
C12 C13 S11 115.5(2) . . ?
C12 C13 H13B 122.3 . . ?
S11 C13 H13B 122.3 . . ?
C12 C13 H13A 126.1 . . ?
C21 C13 H13A 126.1 . . ?

_refine_diff_density_max         0.861
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.061

