# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1566968'
_audit_update_record             
;
2017-08-04 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 B F4 N4 O2 S'
_chemical_formula_weight         519.34

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'
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                   10.495(3)
_cell_length_b                   10.849(3)
_cell_length_c                   12.002(4)
_cell_angle_alpha                93.109(7)
_cell_angle_beta                 103.855(7)
_cell_angle_gamma                104.760(8)
_cell_volume                     1273.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    894
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26.8

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             538
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7874
_exptl_absorpt_correction_T_max  0.8136
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker SMART CCD APEX II 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            10653
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         29.46
_reflns_number_total             6438
_reflns_number_gt                3675
_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)+(0.1337P)²+1.4723P] 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       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6438
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.0932
_refine_ls_wR_factor_ref         0.2924
_refine_ls_wR_factor_gt          0.2497
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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 0.71212(10) 0.18113(9) 0.46554(9) 0.0537(3) Uani 1 1 d . . .
C25 C 0.7013(3) 0.4212(3) 0.5494(3) 0.0419(8) Uani 1 1 d . . .
C26 C 0.6815(3) 0.5439(3) 0.5287(3) 0.0423(8) Uani 1 1 d . . .
N4 N 0.8765(3) 0.2039(3) 0.5174(3) 0.0509(8) Uani 1 1 d . . .
H4A H 0.9053 0.1668 0.5760 0.061 Uiso 1 1 calc R . .
C12 C 0.6841(4) 0.3338(4) 0.4521(3) 0.0472(8) Uani 1 1 d . . .
C27 C 0.6970(3) 0.6366(3) 0.6230(3) 0.0466(8) Uani 1 1 d . . .
C18 C 0.6780(4) 0.7588(4) 0.6024(4) 0.0569(10) Uani 1 1 d . . .
O2 O 0.6788(3) 0.1163(3) 0.3515(3) 0.0700(9) Uani 1 1 d . . .
C24 C 0.7349(4) 0.3953(4) 0.6665(3) 0.0520(9) Uani 1 1 d . . .
H24A H 0.7484 0.3158 0.6819 0.062 Uiso 1 1 calc R . .
O1 O 0.6516(3) 0.1201(3) 0.5491(3) 0.0721(9) Uani 1 1 d . . .
C22 C 0.7300(4) 0.6066(4) 0.7377(4) 0.0525(9) Uani 1 1 d . . .
N3 N 0.9434(4) 0.1378(3) 0.2866(3) 0.0548(8) Uani 1 1 d . . .
C15 C 0.6457(4) 0.5749(4) 0.4144(3) 0.0486(9) Uani 1 1 d . . .
C9 C 0.9267(4) 0.3261(4) 0.2536(4) 0.0544(10) Uani 1 1 d . . .
H9A H 0.9236 0.4111 0.2608 0.065 Uiso 1 1 calc R . .
C14 C 0.6274(4) 0.4838(5) 0.3224(4) 0.0589(11) Uani 1 1 d . . .
H14A H 0.6017 0.5029 0.2471 0.071 Uiso 1 1 calc R . .
N1 N 0.9105(4) 0.2522(4) 0.1565(3) 0.0596(9) Uani 1 1 d . . .
C11 C 0.9754(4) 0.2860(4) 0.4663(3) 0.0541(9) Uani 1 1 d . . .
H11A H 1.0660 0.2800 0.5039 0.065 Uiso 1 1 calc R . .
H11B H 0.9745 0.3744 0.4814 0.065 Uiso 1 1 calc R . .
C10 C 0.9488(4) 0.2524(4) 0.3404(4) 0.0509(9) Uani 1 1 d . . .
C23 C 0.7477(4) 0.4826(4) 0.7553(3) 0.0563(10) Uani 1 1 d . . .
H23A H 0.7686 0.4614 0.8303 0.068 Uiso 1 1 calc R . .
C13 C 0.6469(4) 0.3657(4) 0.3413(4) 0.0549(10) Uani 1 1 d . . .
H13A H 0.6349 0.3059 0.2784 0.066 Uiso 1 1 calc R . .
C17 C 0.6438(4) 0.7868(4) 0.4856(5) 0.0657(12) Uani 1 1 d . . .
H17A H 0.6316 0.8670 0.4713 0.079 Uiso 1 1 calc R . .
N2 N 0.9187(4) 0.1356(4) 0.1741(3) 0.0666(10) Uani 1 1 d . . .
C16 C 0.6291(4) 0.7010(5) 0.3975(4) 0.0632(12) Uani 1 1 d . . .
H16A H 0.6076 0.7227 0.3227 0.076 Uiso 1 1 calc R . .
C6 C 0.7243(6) 0.2458(4) -0.0136(4) 0.0658(12) Uani 1 1 d . . .
C21 C 0.7430(5) 0.6974(5) 0.8281(4) 0.0700(12) Uani 1 1 d . . .
H21A H 0.7639 0.6782 0.9037 0.084 Uiso 1 1 calc R . .
C19 C 0.6923(5) 0.8475(4) 0.6966(5) 0.0760(14) Uani 1 1 d . . .
H19A H 0.6796 0.9279 0.6843 0.091 Uiso 1 1 calc R . .
C7 C 0.8761(6) 0.2831(6) 0.0370(4) 0.0765(14) Uani 1 1 d . . .
H7A H 0.9174 0.2377 -0.0098 0.092 Uiso 1 1 calc R . .
H7B H 0.9130 0.3745 0.0361 0.092 Uiso 1 1 calc R . .
C20 C 0.7251(6) 0.8164(5) 0.8068(6) 0.0857(16) Uani 1 1 d . . .
H20A H 0.7355 0.8767 0.8687 0.103 Uiso 1 1 calc R . .
C8 C 0.9590(6) 0.0217(5) 0.3373(5) 0.0790(15) Uani 1 1 d . . .
H8A H 0.9508 -0.0442 0.2773 0.119 Uiso 1 1 calc R . .
H8B H 0.8893 -0.0068 0.3768 0.119 Uiso 1 1 calc R . .
H8C H 1.0472 0.0397 0.3912 0.119 Uiso 1 1 calc R . .
C5 C 0.6453(6) 0.3193(6) 0.0156(5) 0.0815(15) Uani 1 1 d . . .
H5A H 0.6872 0.3955 0.0650 0.098 Uiso 1 1 calc R . .
C1 C 0.6647(9) 0.1421(7) -0.0904(7) 0.137(3) Uani 1 1 d . . .
H1B H 0.7184 0.0956 -0.1146 0.164 Uiso 1 1 calc R . .
C4 C 0.5075(8) 0.2826(9) -0.0264(6) 0.109(2) Uani 1 1 d . . .
H4B H 0.4555 0.3330 -0.0053 0.131 Uiso 1 1 calc R . .
C2 C 0.5260(13) 0.1019(9) -0.1349(10) 0.190(6) Uani 1 1 d . . .
H2C H 0.4861 0.0285 -0.1882 0.228 Uiso 1 1 calc R . .
C3 C 0.4455(9) 0.1715(11) -0.0999(8) 0.149(4) Uani 1 1 d . . .
H3A H 0.3508 0.1430 -0.1259 0.179 Uiso 1 1 calc R . .
F4 F 1.0402(4) 0.7778(3) 0.2140(3) 0.1020(11) Uani 1 1 d . . .
F3 F 0.9197(4) 0.6184(4) 0.2842(3) 0.1201(13) Uani 1 1 d . . .
F2 F 0.9344(5) 0.5883(4) 0.1084(4) 0.1361(17) Uani 1 1 d . . .
B1 B 0.9219(6) 0.6783(6) 0.1861(4) 0.0678(14) Uani 1 1 d . . .
F1 F 0.8153(7) 0.7140(9) 0.1451(6) 0.242(4) 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 O1 1.418(3) . ?
S1 O2 1.425(3) . ?
S1 N4 1.636(3) . ?
S1 C12 1.764(4) . ?
C25 C12 1.409(5) . ?
C25 C26 1.424(5) . ?
C25 C24 1.427(5) . ?
C26 C15 1.415(5) . ?
C26 C27 1.423(5) . ?
N4 C11 1.463(5) . ?
C12 C13 1.383(6) . ?
C27 C22 1.415(6) . ?
C27 C18 1.416(5) . ?
C18 C19 1.398(6) . ?
C18 C17 1.431(6) . ?
C24 C23 1.345(6) . ?
C22 C21 1.383(6) . ?
C22 C23 1.424(6) . ?
N3 N2 1.311(5) . ?
N3 C10 1.351(5) . ?
N3 C8 1.457(5) . ?
C15 C14 1.385(6) . ?
C15 C16 1.442(6) . ?
C9 N1 1.328(5) . ?
C9 C10 1.360(6) . ?
C14 C13 1.370(6) . ?
N1 N2 1.316(5) . ?
N1 C7 1.471(6) . ?
C11 C10 1.477(6) . ?
C17 C16 1.323(6) . ?
C6 C1 1.327(8) . ?
C6 C5 1.375(7) . ?
C6 C7 1.500(7) . ?
C21 C20 1.379(7) . ?
C19 C20 1.368(8) . ?
C5 C4 1.357(9) . ?
C1 C2 1.369(13) . ?
C4 C3 1.366(12) . ?
C2 C3 1.387(15) . ?
F4 B1 1.377(7) . ?
F3 B1 1.378(7) . ?
F2 B1 1.366(6) . ?
B1 F1 1.274(7) . ?

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 S1 O2 119.4(2) . . ?
O1 S1 N4 105.4(2) . . ?
O2 S1 N4 105.89(17) . . ?
O1 S1 C12 111.17(18) . . ?
O2 S1 C12 107.11(19) . . ?
N4 S1 C12 107.16(17) . . ?
C12 C25 C26 117.3(3) . . ?
C12 C25 C24 125.0(3) . . ?
C26 C25 C24 117.7(3) . . ?
C15 C26 C27 119.2(3) . . ?
C15 C26 C25 120.6(3) . . ?
C27 C26 C25 120.2(3) . . ?
C11 N4 S1 121.5(3) . . ?
C13 C12 C25 121.0(4) . . ?
C13 C12 S1 117.0(3) . . ?
C25 C12 S1 122.0(3) . . ?
C22 C27 C18 119.7(4) . . ?
C22 C27 C26 120.1(3) . . ?
C18 C27 C26 120.2(4) . . ?
C19 C18 C27 119.0(4) . . ?
C19 C18 C17 122.3(4) . . ?
C27 C18 C17 118.7(4) . . ?
C23 C24 C25 121.8(3) . . ?
C21 C22 C27 119.2(4) . . ?
C21 C22 C23 122.6(4) . . ?
C27 C22 C23 118.2(4) . . ?
N2 N3 C10 112.7(3) . . ?
N2 N3 C8 118.7(3) . . ?
C10 N3 C8 128.6(4) . . ?
C14 C15 C26 119.3(3) . . ?
C14 C15 C16 122.0(4) . . ?
C26 C15 C16 118.7(4) . . ?
N1 C9 C10 106.0(4) . . ?
C13 C14 C15 120.6(4) . . ?
N2 N1 C9 112.8(3) . . ?
N2 N1 C7 118.9(4) . . ?
C9 N1 C7 128.1(4) . . ?
N4 C11 C10 113.6(3) . . ?
N3 C10 C9 104.6(4) . . ?
N3 C10 C11 126.0(4) . . ?
C9 C10 C11 129.4(4) . . ?
C24 C23 C22 121.9(4) . . ?
C14 C13 C12 121.1(4) . . ?
C16 C17 C18 121.4(4) . . ?
N3 N2 N1 103.8(3) . . ?
C17 C16 C15 121.8(4) . . ?
C1 C6 C5 118.9(6) . . ?
C1 C6 C7 119.9(6) . . ?
C5 C6 C7 121.2(5) . . ?
C20 C21 C22 120.5(5) . . ?
C20 C19 C18 120.2(4) . . ?
N1 C7 C6 111.0(4) . . ?
C19 C20 C21 121.4(5) . . ?
C4 C5 C6 121.2(6) . . ?
C6 C1 C2 121.6(8) . . ?
C5 C4 C3 119.8(7) . . ?
C1 C2 C3 119.5(8) . . ?
C4 C3 C2 118.9(8) . . ?
F1 B1 F2 110.1(6) . . ?
F1 B1 F4 113.3(7) . . ?
F2 B1 F4 108.4(5) . . ?
F1 B1 F3 114.1(6) . . ?
F2 B1 F3 104.3(5) . . ?
F4 B1 F3 106.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        29.46
_diffrn_measured_fraction_theta_full 0.912
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.067
