# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_123
_database_code_depnum_ccdc_archive 'CCDC 1875790'
loop_
_audit_author_name
_audit_author_address
1
;Hangzhou Normal University
China
;
_audit_update_record             
;
2018-10-29 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1
_chemical_name_common            1
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H6 B F5 N2 O0 S4'
_chemical_formula_weight         484.30

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'
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'
B B 0.0013 0.0007 '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                   8.209(2)
_cell_length_b                   9.719(3)
_cell_length_c                   12.587(5)
_cell_angle_alpha                111.424(6)
_cell_angle_beta                 104.496(7)
_cell_angle_gamma                96.556(4)
_cell_volume                     881.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2518
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.29

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10962
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4033
_reflns_number_gt                2691
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0817P)²+0.0087P] 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         4033
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1543
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
S1 S 0.36373(13) 0.41395(11) 0.36158(8) 0.0449(3) Uani 1 1 d . . .
S2 S 0.34690(12) -0.01802(11) 0.57834(8) 0.0413(2) Uani 1 1 d . . .
S3 S -0.08012(13) -0.38580(11) 0.43986(9) 0.0443(3) Uani 1 1 d . . .
S4 S -0.05154(13) 0.36338(11) 0.06519(9) 0.0469(3) Uani 1 1 d . . .
F1 F 0.2233(3) 0.1197(2) 0.38874(17) 0.0452(5) Uani 1 1 d . . .
F2 F 0.2443(2) -0.0659(2) 0.22394(18) 0.0433(5) Uani 1 1 d . . .
F3 F -0.5177(3) -0.2387(3) 0.0683(2) 0.0625(7) Uani 1 1 d . . .
F4 F -0.4391(3) -0.2173(3) -0.0760(2) 0.0673(7) Uani 1 1 d . . .
N2 N 0.0157(3) 0.0652(3) 0.1961(2) 0.0328(6) Uani 1 1 d . . .
N1 N 0.0038(3) -0.1131(3) 0.2920(2) 0.0326(6) Uani 1 1 d . . .
C7 C 0.2339(5) -0.2270(4) 0.6406(3) 0.0414(8) Uani 1 1 d . . .
H7 H 0.2257 -0.2867 0.6831 0.050 Uiso 1 1 calc R . .
C16 C 0.1761(4) 0.3352(4) 0.2418(3) 0.0341(7) Uani 1 1 d . . .
C18 C 0.1121(5) -0.2504(4) 0.5305(3) 0.0370(8) Uani 1 1 d . . .
C2 C -0.2193(4) -0.3190(4) 0.2305(3) 0.0372(8) Uani 1 1 d . . .
H2 H -0.3204 -0.3937 0.1855 0.045 Uiso 1 1 calc R . .
C11 C -0.2004(4) 0.0600(4) 0.0371(3) 0.0369(8) Uani 1 1 d . . .
H11 H -0.2999 0.0276 -0.0287 0.044 Uiso 1 1 calc R . .
C9 C -0.2197(4) -0.1565(4) 0.1095(3) 0.0333(7) Uani 1 1 d . . .
C15 C 0.3875(5) 0.5784(4) 0.3399(3) 0.0504(10) Uani 1 1 d . . .
H15 H 0.4792 0.6617 0.3883 0.060 Uiso 1 1 calc R . .
C17 C 0.0507(4) 0.1955(4) 0.1832(3) 0.0318(7) Uani 1 1 d . . .
C4 C 0.0323(4) -0.1739(4) 0.3747(3) 0.0316(7) Uani 1 1 d . . .
C6 C 0.3656(5) -0.1044(5) 0.6756(3) 0.0469(9) Uani 1 1 d . . .
H6 H 0.4575 -0.0708 0.7464 0.056 Uiso 1 1 calc R . .
C3 C -0.1059(4) -0.3005(4) 0.3381(3) 0.0343(7) Uani 1 1 d . . .
C12 C -0.0826(4) 0.1954(4) 0.0850(3) 0.0372(8) Uani 1 1 d . . .
C14 C 0.2602(5) 0.5767(4) 0.2453(3) 0.0472(9) Uani 1 1 d . . .
H14 H 0.2545 0.6565 0.2215 0.057 Uiso 1 1 calc R . .
C8 C -0.3902(5) -0.2504(4) 0.0184(3) 0.0399(8) Uani 1 1 d . . .
B1 B 0.1316(5) 0.0040(4) 0.2795(3) 0.0310(8) Uani 1 1 d . . .
C5 C 0.1554(4) -0.1443(4) 0.4851(3) 0.0334(7) Uani 1 1 d . . .
C1 C -0.1506(4) -0.2003(4) 0.2016(3) 0.0323(7) Uani 1 1 d . . .
C10 C -0.1419(4) -0.0221(4) 0.1069(3) 0.0340(7) Uani 1 1 d . . .
C13 C 0.1383(5) 0.4354(4) 0.1888(3) 0.0392(8) Uani 1 1 d . . .
F5 F -0.3912(3) -0.3985(2) -0.0250(2) 0.0600(6) 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 C15 1.715(4) . ?
S1 C16 1.719(4) . ?
S2 C6 1.707(4) . ?
S2 C5 1.714(3) . ?
S3 C18 1.747(4) . ?
S3 C3 1.747(3) . ?
S4 C12 1.739(4) . ?
S4 C13 1.755(4) . ?
F1 B1 1.372(4) . ?
F2 B1 1.388(4) . ?
F3 C8 1.344(4) . ?
F4 C8 1.322(4) . ?
N2 C17 1.343(4) . ?
N2 C10 1.407(4) . ?
N2 B1 1.564(4) . ?
N1 C4 1.360(4) . ?
N1 C1 1.396(4) . ?
N1 B1 1.536(4) . ?
C7 C6 1.366(5) . ?
C7 C18 1.413(5) . ?
C7 H7 0.9300 . ?
C16 C13 1.389(4) . ?
C16 C17 1.420(5) . ?
C18 C5 1.401(4) . ?
C2 C3 1.373(5) . ?
C2 C1 1.429(4) . ?
C2 H2 0.9300 . ?
C11 C12 1.367(5) . ?
C11 C10 1.424(4) . ?
C11 H11 0.9300 . ?
C9 C1 1.391(4) . ?
C9 C10 1.401(4) . ?
C9 C8 1.499(4) . ?
C15 C14 1.366(6) . ?
C15 H15 0.9300 . ?
C17 C12 1.431(4) . ?
C4 C5 1.405(4) . ?
C4 C3 1.421(4) . ?
C6 H6 0.9300 . ?
C14 C13 1.417(5) . ?
C14 H14 0.9300 . ?
C8 F5 1.339(4) . ?

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
C15 S1 C16 90.80(18) . . ?
C6 S2 C5 91.17(17) . . ?
C18 S3 C3 89.72(16) . . ?
C12 S4 C13 89.54(16) . . ?
C17 N2 C10 107.0(3) . . ?
C17 N2 B1 129.1(3) . . ?
C10 N2 B1 123.4(3) . . ?
C4 N1 C1 107.5(3) . . ?
C4 N1 B1 127.9(3) . . ?
C1 N1 B1 123.3(3) . . ?
C6 C7 C18 110.4(3) . . ?
C6 C7 H7 124.8 . . ?
C18 C7 H7 124.8 . . ?
C13 C16 C17 112.1(3) . . ?
C13 C16 S1 111.1(3) . . ?
C17 C16 S1 136.8(3) . . ?
C5 C18 C7 113.3(3) . . ?
C5 C18 S3 114.0(3) . . ?
C7 C18 S3 132.7(3) . . ?
C3 C2 C1 106.2(3) . . ?
C3 C2 H2 126.9 . . ?
C1 C2 H2 126.9 . . ?
C12 C11 C10 107.1(3) . . ?
C12 C11 H11 126.5 . . ?
C10 C11 H11 126.5 . . ?
C1 C9 C10 121.7(3) . . ?
C1 C9 C8 117.6(3) . . ?
C10 C9 C8 120.5(3) . . ?
C14 C15 S1 114.3(3) . . ?
C14 C15 H15 122.8 . . ?
S1 C15 H15 122.8 . . ?
N2 C17 C16 138.6(3) . . ?
N2 C17 C12 110.1(3) . . ?
C16 C17 C12 111.2(3) . . ?
N1 C4 C5 138.0(3) . . ?
N1 C4 C3 109.0(3) . . ?
C5 C4 C3 112.9(3) . . ?
C7 C6 S2 114.3(3) . . ?
C7 C6 H6 122.9 . . ?
S2 C6 H6 122.9 . . ?
C2 C3 C4 108.4(3) . . ?
C2 C3 S3 139.4(3) . . ?
C4 C3 S3 112.2(2) . . ?
C11 C12 C17 107.3(3) . . ?
C11 C12 S4 139.5(3) . . ?
C17 C12 S4 113.2(3) . . ?
C15 C14 C13 110.0(3) . . ?
C15 C14 H14 125.0 . . ?
C13 C14 H14 125.0 . . ?
F4 C8 F5 106.2(3) . . ?
F4 C8 F3 106.9(3) . . ?
F5 C8 F3 104.8(3) . . ?
F4 C8 C9 115.3(3) . . ?
F5 C8 C9 111.7(3) . . ?
F3 C8 C9 111.2(3) . . ?
F1 B1 F2 109.9(3) . . ?
F1 B1 N1 111.8(3) . . ?
F2 B1 N1 110.3(3) . . ?
F1 B1 N2 110.8(3) . . ?
F2 B1 N2 109.4(3) . . ?
N1 B1 N2 104.6(3) . . ?
C18 C5 C4 111.2(3) . . ?
C18 C5 S2 110.8(2) . . ?
C4 C5 S2 138.0(3) . . ?
C9 C1 N1 120.1(3) . . ?
C9 C1 C2 130.8(3) . . ?
N1 C1 C2 108.9(3) . . ?
C9 C10 N2 118.8(3) . . ?
C9 C10 C11 132.3(3) . . ?
N2 C10 C11 108.5(3) . . ?
C16 C13 C14 113.8(3) . . ?
C16 C13 S4 113.9(3) . . ?
C14 C13 S4 132.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.104
