# 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_n0095b-1
_database_code_depnum_ccdc_archive 'CCDC 1000278'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 B Br F2 N2 O S Se'
_chemical_formula_sum            'C23 H20 B Br F2 N2 O S Se'
_chemical_formula_weight         580.15

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   8.9526(2)
_cell_length_b                   10.2532(3)
_cell_length_c                   14.7976(4)
_cell_angle_alpha                94.4778(14)
_cell_angle_beta                 106.8774(12)
_cell_angle_gamma                114.9387(12)
_cell_volume                     1146.72(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    63841
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.06

_exptl_crystal_description       platy
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    3.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4194
_exptl_absorpt_correction_T_max  0.9021
_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         '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_reflns_number            63841
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         28.06
_reflns_number_total             5542
_reflns_number_gt                4667
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0552P)²+0.5287P] 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         5542
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Se1 Se 0.91805(3) 0.81047(3) 0.436398(17) 0.03856(9) Uani 1 1 d . . .
Br1 Br 0.26919(5) 0.90371(4) 0.31480(3) 0.06718(12) Uani 1 1 d . . .
S1 S 0.61601(8) 0.89272(7) 0.42026(4) 0.03973(15) Uani 1 1 d . . .
B1 B 0.7520(5) 0.4916(5) 0.0854(2) 0.0582(9) Uani 1 1 d . . .
F1 F 0.8931(3) 0.4703(3) 0.13765(14) 0.0764(6) Uani 1 1 d . . .
F2 F 0.6973(3) 0.4274(3) -0.01194(13) 0.0833(7) Uani 1 1 d . . .
N1 N 0.8082(3) 0.6583(3) 0.10047(16) 0.0505(6) Uani 1 1 d . . .
N2 N 0.6000(3) 0.4228(3) 0.12405(17) 0.0525(6) Uani 1 1 d . . .
O1 O 0.9315(3) 0.8709(2) 0.54733(13) 0.0568(5) Uani 1 1 d . . .
C1 C 1.0055(6) 0.7178(6) 0.0032(3) 0.0849(13) Uani 1 1 d . . .
H1A H 0.9649 0.6130 -0.0091 0.127 Uiso 1 1 calc R . .
H1B H 1.1312 0.7685 0.0357 0.127 Uiso 1 1 calc R . .
H1C H 0.9752 0.7459 -0.0572 0.127 Uiso 1 1 calc R . .
C2 C 0.9196(4) 0.7584(4) 0.0662(2) 0.0596(8) Uani 1 1 d . . .
C3 C 0.9436(4) 0.8981(4) 0.1014(2) 0.0574(8) Uani 1 1 d . . .
H3A H 1.0138 0.9851 0.0874 0.069 Uiso 1 1 calc R . .
C4 C 0.8466(4) 0.8867(3) 0.16032(18) 0.0456(6) Uani 1 1 d . . .
C5 C 0.8410(5) 1.0158(3) 0.2123(2) 0.0555(7) Uani 1 1 d . . .
H5A H 0.9151 1.1051 0.1981 0.083 Uiso 1 1 calc R . .
H5B H 0.8823 1.0232 0.2810 0.083 Uiso 1 1 calc R . .
H5C H 0.7219 1.0014 0.1910 0.083 Uiso 1 1 calc R . .
C6 C 0.7593(4) 0.7341(3) 0.15966(17) 0.0427(6) Uani 1 1 d . . .
C7 C 0.5217(7) 0.1589(5) 0.0650(3) 0.0972(16) Uani 1 1 d . . .
H7A H 0.6103 0.2025 0.0370 0.146 Uiso 1 1 calc R . .
H7B H 0.4108 0.0943 0.0144 0.146 Uiso 1 1 calc R . .
H7C H 0.5550 0.1034 0.1088 0.146 Uiso 1 1 calc R . .
C8 C 0.5046(5) 0.2788(4) 0.1195(3) 0.0675(10) Uani 1 1 d . . .
C9 C 0.3945(5) 0.2623(4) 0.1717(3) 0.0727(10) Uani 1 1 d . . .
H9A H 0.3153 0.1727 0.1786 0.087 Uiso 1 1 calc R . .
C10 C 0.4209(4) 0.4000(3) 0.2118(2) 0.0546(7) Uani 1 1 d . . .
C11 C 0.3261(5) 0.4271(4) 0.2725(3) 0.0696(9) Uani 1 1 d . . .
H11A H 0.2463 0.3345 0.2806 0.104 Uiso 1 1 calc R . .
H11B H 0.2610 0.4754 0.2413 0.104 Uiso 1 1 calc R . .
H11C H 0.4098 0.4888 0.3349 0.104 Uiso 1 1 calc R . .
C12 C 0.5520(4) 0.5025(3) 0.18137(18) 0.0453(6) Uani 1 1 d . . .
C13 C 0.6355(3) 0.6559(3) 0.19998(16) 0.0395(5) Uani 1 1 d . . .
C14 C 0.5937(3) 0.7397(3) 0.26658(17) 0.0366(5) Uani 1 1 d . . .
C15 C 0.4439(4) 0.7653(3) 0.23924(19) 0.0455(6) Uani 1 1 d . . .
H15A H 0.3588 0.7310 0.1772 0.055 Uiso 1 1 calc R . .
C16 C 0.4414(3) 0.8457(3) 0.3151(2) 0.0423(5) Uani 1 1 d . . .
C17 C 0.6968(3) 0.8017(2) 0.36160(16) 0.0332(5) Uani 1 1 d . . .
C18 C 0.8310(4) 0.6002(3) 0.4244(2) 0.0451(6) Uani 1 1 d . . .
C19 C 0.8817(5) 0.5277(4) 0.3669(2) 0.0619(8) Uani 1 1 d . . .
H19A H 0.9519 0.5783 0.3330 0.074 Uiso 1 1 calc R . .
C20 C 0.8263(7) 0.3784(5) 0.3605(4) 0.0972(17) Uani 1 1 d . . .
H20A H 0.8604 0.3275 0.3228 0.117 Uiso 1 1 calc R . .
C21 C 0.7213(8) 0.3059(5) 0.4097(5) 0.119(2) Uani 1 1 d . . .
H21A H 0.6829 0.2052 0.4048 0.142 Uiso 1 1 calc R . .
C22 C 0.6720(7) 0.3797(6) 0.4663(5) 0.114(2) Uani 1 1 d . . .
H22A H 0.5994 0.3283 0.4988 0.137 Uiso 1 1 calc R . .
C23 C 0.7283(5) 0.5298(4) 0.4759(3) 0.0743(10) Uani 1 1 d . . .
H23A H 0.6977 0.5810 0.5157 0.089 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
Se1 O1 1.6602(19) . ?
Se1 C17 1.928(2) . ?
Se1 C18 1.932(3) . ?
Br1 C16 1.871(3) . ?
S1 C16 1.712(3) . ?
S1 C17 1.719(2) . ?
B1 F2 1.385(3) . ?
B1 F1 1.391(4) . ?
B1 N1 1.540(5) . ?
B1 N2 1.543(5) . ?
N1 C2 1.348(4) . ?
N1 C6 1.402(3) . ?
N2 C8 1.342(4) . ?
N2 C12 1.404(3) . ?
C1 C2 1.503(4) . ?
C2 C3 1.388(5) . ?
C3 C4 1.378(4) . ?
C4 C6 1.422(4) . ?
C4 C5 1.505(4) . ?
C6 C13 1.392(4) . ?
C7 C8 1.504(5) . ?
C8 C9 1.385(6) . ?
C9 C10 1.381(4) . ?
C10 C12 1.423(4) . ?
C10 C11 1.485(5) . ?
C12 C13 1.389(4) . ?
C13 C14 1.484(3) . ?
C14 C17 1.359(3) . ?
C14 C15 1.424(4) . ?
C15 C16 1.352(4) . ?
C18 C23 1.371(5) . ?
C18 C19 1.375(4) . ?
C19 C20 1.382(5) . ?
C20 C21 1.363(8) . ?
C21 C22 1.366(9) . ?
C22 C23 1.383(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Se1 C17 99.75(10) . . ?
O1 Se1 C18 103.43(12) . . ?
C17 Se1 C18 96.72(10) . . ?
C16 S1 C17 90.23(12) . . ?
F2 B1 F1 109.0(2) . . ?
F2 B1 N1 110.7(3) . . ?
F1 B1 N1 109.8(3) . . ?
F2 B1 N2 110.7(3) . . ?
F1 B1 N2 109.7(3) . . ?
N1 B1 N2 107.0(2) . . ?
C2 N1 C6 107.8(3) . . ?
C2 N1 B1 127.5(3) . . ?
C6 N1 B1 124.5(3) . . ?
C8 N2 C12 107.5(3) . . ?
C8 N2 B1 126.9(3) . . ?
C12 N2 B1 125.2(3) . . ?
N1 C2 C3 109.4(3) . . ?
N1 C2 C1 122.8(4) . . ?
C3 C2 C1 127.8(4) . . ?
C4 C3 C2 108.9(3) . . ?
C3 C4 C6 106.1(3) . . ?
C3 C4 C5 124.2(3) . . ?
C6 C4 C5 129.7(3) . . ?
C13 C6 N1 120.0(3) . . ?
C13 C6 C4 132.0(2) . . ?
N1 C6 C4 107.9(2) . . ?
N2 C8 C9 109.7(3) . . ?
N2 C8 C7 122.8(4) . . ?
C9 C8 C7 127.5(4) . . ?
C10 C9 C8 109.2(3) . . ?
C9 C10 C12 105.3(3) . . ?
C9 C10 C11 124.9(3) . . ?
C12 C10 C11 129.8(3) . . ?
C13 C12 N2 119.3(3) . . ?
C13 C12 C10 132.4(3) . . ?
N2 C12 C10 108.3(2) . . ?
C12 C13 C6 122.3(2) . . ?
C12 C13 C14 118.9(2) . . ?
C6 C13 C14 118.8(2) . . ?
C17 C14 C15 112.4(2) . . ?
C17 C14 C13 123.0(2) . . ?
C15 C14 C13 124.7(2) . . ?
C16 C15 C14 111.3(2) . . ?
C15 C16 S1 113.6(2) . . ?
C15 C16 Br1 126.7(2) . . ?
S1 C16 Br1 119.60(14) . . ?
C14 C17 S1 112.48(18) . . ?
C14 C17 Se1 130.67(18) . . ?
S1 C17 Se1 116.79(12) . . ?
C23 C18 C19 122.4(3) . . ?
C23 C18 Se1 119.6(3) . . ?
C19 C18 Se1 117.9(2) . . ?
C18 C19 C20 118.7(4) . . ?
C21 C20 C19 119.7(5) . . ?
C20 C21 C22 120.7(4) . . ?
C21 C22 C23 121.0(5) . . ?
C18 C23 C22 117.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.06
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.093
