# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 1879308'
loop_
_audit_author_name
_audit_author_address
Sun-1
;Hangzhou Normal University
China
;
_audit_update_record             
;
2018-11-16 deposited with the CCDC.	2019-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 B F2 N2 S2'
_chemical_formula_weight         332.19

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'

_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                   8.2395(4)
_cell_length_b                   8.3633(4)
_cell_length_c                   21.5671(10)
_cell_angle_alpha                87.1040(10)
_cell_angle_beta                 86.8260(10)
_cell_angle_gamma                79.6960(10)
_cell_volume                     1458.72(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2720
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      27.91

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.382
_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            28587
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         0.95
_diffrn_reflns_theta_max         27.45
_reflns_number_total             6680
_reflns_number_gt                5061
_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)+(0.0725P)²+0.4701P] 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         6680
_refine_ls_number_parameters     401
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.033
_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
S1 S 0.18796(7) 0.67641(8) 0.48062(3) 0.05289(16) Uani 1 1 d . . .
S2 S 0.56319(8) 0.67877(8) 0.60388(3) 0.05439(17) Uani 1 1 d . . .
S3 S 1.25412(10) 0.43679(9) 0.78119(3) 0.0677(2) Uani 1 1 d . . .
S4 S 0.73700(10) 0.48549(9) 0.78631(4) 0.0741(2) Uani 1 1 d . . .
F1 F 0.5053(2) 0.70101(16) 0.34372(6) 0.0631(4) Uani 1 1 d . . .
F3 F 0.69452(16) 0.55703(17) 0.94184(7) 0.0602(4) Uani 1 1 d . . .
F2 F 0.32734(15) 0.92358(18) 0.37444(6) 0.0583(4) Uani 1 1 d . . .
N1 N 0.5943(2) 0.9576(2) 0.32680(8) 0.0435(4) Uani 1 1 d . . .
N3 N 0.79118(19) 0.7568(2) 1.00169(8) 0.0397(4) Uani 1 1 d . . .
F4 F 0.69060(17) 0.80863(18) 0.89866(7) 0.0646(4) Uani 1 1 d . . .
C13 C 0.3731(2) 0.7004(2) 0.50855(9) 0.0407(4) Uani 1 1 d . . .
N2 N 0.5689(2) 0.8350(2) 0.43316(7) 0.0390(4) Uani 1 1 d . . .
N4 N 0.9547(2) 0.6353(2) 0.91006(8) 0.0396(4) Uani 1 1 d . . .
C22 C 0.9382(2) 0.7860(2) 1.02460(9) 0.0384(4) Uani 1 1 d . . .
C14 C 0.5124(2) 0.7672(2) 0.48660(9) 0.0387(4) Uani 1 1 d . . .
C10 C 0.3846(3) 0.6471(2) 0.57046(10) 0.0458(5) Uani 1 1 d . . .
C9 C 0.6257(3) 0.7659(3) 0.53361(9) 0.0444(5) Uani 1 1 d . . .
C5 C 0.7446(2) 0.9962(2) 0.34222(10) 0.0455(5) Uani 1 1 d . . .
C6 C 0.8044(3) 0.9575(3) 0.40007(11) 0.0466(5) Uani 1 1 d . . .
H6 H 0.9054 0.9840 0.4088 0.056 Uiso 1 1 calc R . .
C31 C 0.9326(3) 0.4958(3) 0.80751(11) 0.0534(6) Uani 1 1 d . . .
C21 C 0.9020(3) 0.8615(3) 1.08253(10) 0.0444(5) Uani 1 1 d . . .
C23 C 1.0858(2) 0.7393(2) 0.99259(9) 0.0413(4) Uani 1 1 d . . .
H23 H 1.1818 0.7594 1.0091 0.050 Uiso 1 1 calc R . .
C7 C 0.7186(2) 0.8797(3) 0.44613(10) 0.0432(5) Uani 1 1 d . . .
C24 C 1.0975(2) 0.6631(3) 0.93631(10) 0.0423(4) Uani 1 1 d . . .
C32 C 1.0050(3) 0.5590(2) 0.85687(10) 0.0451(5) Uani 1 1 d . . .
C26 C 1.1787(3) 0.5372(3) 0.84871(10) 0.0507(5) Uani 1 1 d . . .
C8 C 0.7537(3) 0.8372(3) 0.50854(10) 0.0485(5) Uani 1 1 d . . .
H8 H 0.8455 0.8540 0.5288 0.058 Uiso 1 1 calc R . .
C19 C 0.6691(3) 0.8104(3) 1.04344(11) 0.0502(5) Uani 1 1 d . . .
C25 C 1.2377(3) 0.6021(3) 0.89852(11) 0.0514(5) Uani 1 1 d . . .
H25 H 1.3473 0.6052 0.9057 0.062 Uiso 1 1 calc R . .
C11 C 0.2451(3) 0.5839(3) 0.59468(11) 0.0555(6) Uani 1 1 d . . .
H11 H 0.2336 0.5416 0.6351 0.067 Uiso 1 1 calc R . .
C20 C 0.7346(3) 0.8760(3) 1.09321(11) 0.0553(6) Uani 1 1 d . . .
H20 H 0.6744 0.9217 1.1277 0.066 Uiso 1 1 calc R . .
C35 C 1.0246(3) 0.9106(3) 1.12271(11) 0.0553(6) Uani 1 1 d . . .
H35A H 1.0408 1.0188 1.1104 0.083 Uiso 1 1 calc R . .
H35B H 1.1277 0.8367 1.1182 0.083 Uiso 1 1 calc R . .
H35C H 0.9843 0.9080 1.1653 0.083 Uiso 1 1 calc R . .
C2 C 0.5627(3) 1.0188(3) 0.26883(10) 0.0529(6) Uani 1 1 d . . .
C4 C 0.8078(3) 1.0834(3) 0.29045(11) 0.0535(6) Uani 1 1 d . . .
C12 C 0.1306(3) 0.5928(3) 0.55175(12) 0.0591(6) Uani 1 1 d . . .
H12 H 0.0304 0.5574 0.5596 0.071 Uiso 1 1 calc R . .
C34 C 0.4930(3) 0.7967(4) 1.03592(16) 0.0723(8) Uani 1 1 d . . .
H34A H 0.4650 0.8249 0.9937 0.109 Uiso 1 1 calc R . .
H34B H 0.4228 0.8695 1.0631 0.109 Uiso 1 1 calc R . .
H34C H 0.4781 0.6871 1.0461 0.109 Uiso 1 1 calc R . .
B1 B 0.4919(3) 0.8527(3) 0.36910(11) 0.0426(5) Uani 1 1 d . . .
B2 B 0.7762(3) 0.6880(3) 0.93701(11) 0.0419(5) Uani 1 1 d . . .
C3 C 0.6930(3) 1.0978(3) 0.24618(11) 0.0586(6) Uani 1 1 d . . .
H3 H 0.6997 1.1510 0.2074 0.070 Uiso 1 1 calc R . .
C27 C 1.0522(4) 0.4264(3) 0.76390(11) 0.0629(7) Uani 1 1 d . . .
C17 C 0.9694(3) 1.1412(3) 0.28740(14) 0.0696(7) Uani 1 1 d . . .
H17A H 0.9964 1.1732 0.2453 0.104 Uiso 1 1 calc R . .
H17B H 1.0540 1.0550 0.3017 0.104 Uiso 1 1 calc R . .
H17C H 0.9618 1.2326 0.3133 0.104 Uiso 1 1 calc R . .
C28 C 0.9843(5) 0.3645(3) 0.71359(14) 0.0792(9) Uani 1 1 d U . .
H28 H 1.0464 0.3139 0.6804 0.095 Uiso 1 1 calc R . .
C16 C 0.4140(3) 1.0004(4) 0.23651(12) 0.0743(8) Uani 1 1 d . . .
H16A H 0.4022 0.8881 0.2387 0.112 Uiso 1 1 calc R . .
H16B H 0.4250 1.0365 0.1938 0.112 Uiso 1 1 calc R . .
H16C H 0.3184 1.0646 0.2560 0.112 Uiso 1 1 calc R . .
C29 C 0.8182(6) 0.3876(4) 0.71950(15) 0.0895(10) Uani 1 1 d U . .
H29 H 0.7532 0.3542 0.6905 0.107 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
S1 C13 1.718(2) . ?
S1 C12 1.731(2) . ?
S2 C9 1.741(2) . ?
S2 C10 1.741(2) . ?
S3 C27 1.743(3) . ?
S3 C26 1.746(2) . ?
S4 C31 1.718(3) . ?
S4 C29 1.735(4) . ?
F1 B1 1.391(3) . ?
F3 B2 1.381(3) . ?
F2 B1 1.380(3) . ?
N1 C2 1.348(3) . ?
N1 C5 1.396(3) . ?
N1 B1 1.553(3) . ?
N3 C19 1.343(3) . ?
N3 C22 1.398(2) . ?
N3 B2 1.555(3) . ?
F4 B2 1.387(3) . ?
C13 C10 1.389(3) . ?
C13 C14 1.413(3) . ?
N2 C14 1.355(2) . ?
N2 C7 1.397(3) . ?
N2 B1 1.542(3) . ?
N4 C32 1.350(3) . ?
N4 C24 1.394(3) . ?
N4 B2 1.548(3) . ?
C22 C23 1.368(3) . ?
C22 C21 1.421(3) . ?
C14 C9 1.414(3) . ?
C10 C11 1.413(3) . ?
C9 C8 1.374(3) . ?
C5 C6 1.369(3) . ?
C5 C4 1.428(3) . ?
C6 C7 1.390(3) . ?
C6 H6 0.9300 . ?
C31 C27 1.393(4) . ?
C31 C32 1.417(3) . ?
C21 C20 1.371(3) . ?
C21 C35 1.490(3) . ?
C23 C24 1.390(3) . ?
C23 H23 0.9300 . ?
C7 C8 1.407(3) . ?
C24 C25 1.409(3) . ?
C32 C26 1.412(3) . ?
C26 C25 1.377(3) . ?
C8 H8 0.9300 . ?
C19 C20 1.405(3) . ?
C19 C34 1.494(3) . ?
C25 H25 0.9300 . ?
C11 C12 1.348(4) . ?
C11 H11 0.9300 . ?
C20 H20 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C2 C3 1.411(3) . ?
C2 C16 1.477(4) . ?
C4 C3 1.367(4) . ?
C4 C17 1.493(3) . ?
C12 H12 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C3 H3 0.9300 . ?
C27 C28 1.410(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C28 C29 1.347(5) . ?
C28 H28 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C29 H29 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
C13 S1 C12 90.70(12) . . ?
C9 S2 C10 89.58(10) . . ?
C27 S3 C26 89.36(12) . . ?
C31 S4 C29 90.26(16) . . ?
C2 N1 C5 107.85(18) . . ?
C2 N1 B1 127.76(19) . . ?
C5 N1 B1 124.28(17) . . ?
C19 N3 C22 107.23(17) . . ?
C19 N3 B2 127.90(17) . . ?
C22 N3 B2 124.69(16) . . ?
C10 C13 C14 111.61(19) . . ?
C10 C13 S1 111.07(16) . . ?
C14 C13 S1 137.21(16) . . ?
C14 N2 C7 106.41(16) . . ?
C14 N2 B1 127.96(17) . . ?
C7 N2 B1 125.54(16) . . ?
C32 N4 C24 106.07(17) . . ?
C32 N4 B2 128.31(17) . . ?
C24 N4 B2 125.60(17) . . ?
C23 C22 N3 120.60(18) . . ?
C23 C22 C21 130.56(19) . . ?
N3 C22 C21 108.82(17) . . ?
N2 C14 C13 138.26(19) . . ?
N2 C14 C9 109.80(18) . . ?
C13 C14 C9 111.93(18) . . ?
C13 C10 C11 113.3(2) . . ?
C13 C10 S2 114.07(17) . . ?
C11 C10 S2 132.58(18) . . ?
C8 C9 C14 107.67(19) . . ?
C8 C9 S2 139.53(17) . . ?
C14 C9 S2 112.79(16) . . ?
C6 C5 N1 121.06(19) . . ?
C6 C5 C4 130.5(2) . . ?
N1 C5 C4 108.4(2) . . ?
C5 C6 C7 122.0(2) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C27 C31 C32 111.3(2) . . ?
C27 C31 S4 111.56(19) . . ?
C32 C31 S4 137.1(2) . . ?
C20 C21 C22 105.76(19) . . ?
C20 C21 C35 128.3(2) . . ?
C22 C21 C35 125.9(2) . . ?
C22 C23 C24 122.42(18) . . ?
C22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C6 C7 N2 119.67(19) . . ?
C6 C7 C8 130.7(2) . . ?
N2 C7 C8 109.57(18) . . ?
C23 C24 N4 119.71(18) . . ?
C23 C24 C25 130.07(19) . . ?
N4 C24 C25 110.22(19) . . ?
N4 C32 C26 110.12(19) . . ?
N4 C32 C31 137.9(2) . . ?
C26 C32 C31 112.0(2) . . ?
C25 C26 C32 107.9(2) . . ?
C25 C26 S3 139.14(19) . . ?
C32 C26 S3 112.99(18) . . ?
C9 C8 C7 106.54(19) . . ?
C9 C8 H8 126.7 . . ?
C7 C8 H8 126.7 . . ?
N3 C19 C20 109.51(19) . . ?
N3 C19 C34 123.1(2) . . ?
C20 C19 C34 127.4(2) . . ?
C26 C25 C24 105.7(2) . . ?
C26 C25 H25 127.1 . . ?
C24 C25 H25 127.1 . . ?
C12 C11 C10 111.4(2) . . ?
C12 C11 H11 124.3 . . ?
C10 C11 H11 124.3 . . ?
C21 C20 C19 108.7(2) . . ?
C21 C20 H20 125.7 . . ?
C19 C20 H20 125.7 . . ?
C21 C35 H35A 109.5 . . ?
C21 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C21 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N1 C2 C3 108.9(2) . . ?
N1 C2 C16 123.3(2) . . ?
C3 C2 C16 127.8(2) . . ?
C3 C4 C5 106.0(2) . . ?
C3 C4 C17 128.9(2) . . ?
C5 C4 C17 125.0(2) . . ?
C11 C12 S1 113.57(19) . . ?
C11 C12 H12 123.2 . . ?
S1 C12 H12 123.2 . . ?
C19 C34 H34A 109.5 . . ?
C19 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C19 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
F2 B1 F1 109.08(19) . . ?
F2 B1 N2 110.48(17) . . ?
F1 B1 N2 110.25(17) . . ?
F2 B1 N1 111.91(17) . . ?
F1 B1 N1 108.68(17) . . ?
N2 B1 N1 106.41(17) . . ?
F3 B2 F4 108.93(17) . . ?
F3 B2 N4 110.33(18) . . ?
F4 B2 N4 110.06(18) . . ?
F3 B2 N3 111.50(17) . . ?
F4 B2 N3 109.59(18) . . ?
N4 B2 N3 106.41(15) . . ?
C4 C3 C2 108.9(2) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
C31 C27 C28 112.9(3) . . ?
C31 C27 S3 114.30(19) . . ?
C28 C27 S3 132.8(3) . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C29 C28 C27 111.6(3) . . ?
C29 C28 H28 124.2 . . ?
C27 C28 H28 124.2 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C28 C29 S4 113.7(2) . . ?
C28 C29 H29 123.1 . . ?
S4 C29 H29 123.1 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1941928'
loop_
_audit_author_name
_audit_author_address
'Sun PH'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H11 B F2 N2 S2'
_chemical_formula_weight         380.23

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5714(19)
_cell_length_b                   12.149(2)
_cell_length_c                   13.188(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1693.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2760
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.91

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_type   none
_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            40129
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         29.58
_reflns_number_total             4748
_reflns_number_gt                3528
_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)+(0.0411P)²+0.3737P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_number_reflns         4748
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.12089(7) -0.35569(5) 0.18658(5) 0.05053(17) Uani 1 1 d . . .
S2 S -0.03135(7) -0.16528(6) -0.04997(5) 0.05296(18) Uani 1 1 d . . .
N1 N 0.13719(18) -0.04092(15) 0.16585(13) 0.0369(4) Uani 1 1 d . . .
N2 N 0.15788(16) 0.16339(15) 0.16447(12) 0.0346(4) Uani 1 1 d . . .
C1 C 0.1095(2) -0.14519(18) 0.13963(16) 0.0373(5) Uani 1 1 d . . .
C2 C 0.0504(2) -0.20053(18) 0.05826(17) 0.0393(5) Uani 1 1 d . . .
C7 C 0.2021(2) -0.1558(2) 0.29413(16) 0.0431(5) Uani 1 1 d . . .
H7 H 0.2360 -0.1814 0.3547 0.052 Uiso 1 1 calc R . .
F1 F 0.1990(2) 0.05591(13) 0.01576(11) 0.0800(6) Uani 1 1 d . . .
C15 C 0.2170(2) 0.3939(2) -0.00266(19) 0.0448(6) Uani 1 1 d . . .
H15 H 0.2869 0.4159 0.0350 0.054 Uiso 1 1 calc R . .
C10 C 0.2065(2) 0.1542(2) 0.26272(15) 0.0383(5) Uani 1 1 d . . .
C5 C 0.0488(2) -0.31400(19) 0.07296(18) 0.0445(6) Uani 1 1 d . . .
C6 C 0.1505(2) -0.21783(18) 0.21761(18) 0.0411(5) Uani 1 1 d . . .
C9 C 0.2253(2) 0.0531(2) 0.30910(16) 0.0405(5) Uani 1 1 d . . .
H9 H 0.2606 0.0510 0.3737 0.049 Uiso 1 1 calc R . .
F2 F -0.00325(16) 0.06560(13) 0.06802(15) 0.0791(6) Uani 1 1 d . . .
C11 C 0.2369(3) 0.2604(2) 0.29769(19) 0.0482(6) Uani 1 1 d . . .
H11 H 0.2685 0.2784 0.3613 0.058 Uiso 1 1 calc R . .
C3 C -0.0635(3) -0.3024(2) -0.0735(2) 0.0598(7) Uani 1 1 d . . .
H3 H -0.1095 -0.3263 -0.1295 0.072 Uiso 1 1 calc R . .
C14 C 0.1329(2) 0.31733(17) 0.03728(17) 0.0376(5) Uani 1 1 d . . .
C8 C 0.1932(2) -0.0445(2) 0.26201(16) 0.0389(5) Uani 1 1 d . . .
C13 C 0.1630(2) 0.27188(18) 0.13803(17) 0.0373(5) Uani 1 1 d . . .
B1 B 0.1202(3) 0.0619(2) 0.09920(19) 0.0411(6) Uani 1 1 d . . .
C12 C 0.2110(3) 0.3322(2) 0.22037(18) 0.0493(6) Uani 1 1 d . . .
H12 H 0.2231 0.4080 0.2221 0.059 Uiso 1 1 calc R . .
C19 C 0.0267(3) 0.2891(2) -0.0189(2) 0.0493(6) Uani 1 1 d . . .
H19 H -0.0320 0.2400 0.0077 0.059 Uiso 1 1 calc R . .
C17 C 0.0940(3) 0.4081(2) -0.1543(2) 0.0563(7) Uani 1 1 d . . .
H17 H 0.0817 0.4375 -0.2186 0.068 Uiso 1 1 calc R . .
C16 C 0.1970(3) 0.4377(2) -0.0984(2) 0.0530(6) Uani 1 1 d . . .
H16 H 0.2546 0.4879 -0.1249 0.064 Uiso 1 1 calc R . .
C4 C -0.0158(3) -0.3716(2) -0.0031(2) 0.0548(7) Uani 1 1 d . . .
H4 H -0.0247 -0.4478 -0.0049 0.066 Uiso 1 1 calc R . .
C18 C 0.0077(3) 0.3337(2) -0.1144(2) 0.0578(7) Uani 1 1 d . . .
H18 H -0.0632 0.3137 -0.1519 0.069 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
S1 C6 1.752(2) . ?
S1 C5 1.756(3) . ?
S2 C2 1.723(2) . ?
S2 C3 1.728(3) . ?
N1 C1 1.345(3) . ?
N1 C8 1.400(3) . ?
N1 B1 1.538(3) . ?
N2 C13 1.364(3) . ?
N2 C10 1.399(3) . ?
N2 B1 1.556(3) . ?
C1 C2 1.412(3) . ?
C1 C6 1.423(3) . ?
C2 C5 1.392(3) . ?
C7 C6 1.373(3) . ?
C7 C8 1.419(3) . ?
C7 H7 0.9300 . ?
F1 B1 1.382(3) . ?
C15 C16 1.386(3) . ?
C15 C14 1.390(3) . ?
C15 H15 0.9300 . ?
C10 C9 1.386(3) . ?
C10 C11 1.408(3) . ?
C5 C4 1.402(3) . ?
C9 C8 1.382(3) . ?
C9 H9 0.9300 . ?
F2 B1 1.369(3) . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C3 C4 1.351(4) . ?
C3 H3 0.9300 . ?
C14 C19 1.388(3) . ?
C14 C13 1.474(3) . ?
C13 C12 1.405(3) . ?
C12 H12 0.9300 . ?
C19 C18 1.386(4) . ?
C19 H19 0.9300 . ?
C17 C16 1.363(4) . ?
C17 C18 1.388(4) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C4 H4 0.9300 . ?
C18 H18 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
C6 S1 C5 90.07(11) . . ?
C2 S2 C3 90.47(13) . . ?
C1 N1 C8 107.17(18) . . ?
C1 N1 B1 126.34(18) . . ?
C8 N1 B1 126.33(19) . . ?
C13 N2 C10 107.42(18) . . ?
C13 N2 B1 129.39(18) . . ?
C10 N2 B1 122.91(18) . . ?
N1 C1 C2 137.7(2) . . ?
N1 C1 C6 109.4(2) . . ?
C2 C1 C6 112.9(2) . . ?
C5 C2 C1 111.8(2) . . ?
C5 C2 S2 110.82(17) . . ?
C1 C2 S2 137.15(17) . . ?
C6 C7 C8 106.1(2) . . ?
C6 C7 H7 127.0 . . ?
C8 C7 H7 127.0 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C9 C10 N2 122.2(2) . . ?
C9 C10 C11 129.4(2) . . ?
N2 C10 C11 108.3(2) . . ?
C2 C5 C4 113.6(2) . . ?
C2 C5 S1 113.53(17) . . ?
C4 C5 S1 132.7(2) . . ?
C7 C6 C1 108.2(2) . . ?
C7 C6 S1 140.15(19) . . ?
C1 C6 S1 111.68(18) . . ?
C8 C9 C10 121.8(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C12 C11 C10 107.1(2) . . ?
C12 C11 H11 126.4 . . ?
C10 C11 H11 126.4 . . ?
C4 C3 S2 113.8(2) . . ?
C4 C3 H3 123.1 . . ?
S2 C3 H3 123.1 . . ?
C19 C14 C15 118.7(2) . . ?
C19 C14 C13 124.3(2) . . ?
C15 C14 C13 117.0(2) . . ?
C9 C8 N1 119.0(2) . . ?
C9 C8 C7 131.8(2) . . ?
N1 C8 C7 109.2(2) . . ?
N2 C13 C12 108.7(2) . . ?
N2 C13 C14 125.70(19) . . ?
C12 C13 C14 125.4(2) . . ?
F2 B1 F1 109.7(2) . . ?
F2 B1 N1 108.0(2) . . ?
F1 B1 N1 110.0(2) . . ?
F2 B1 N2 112.6(2) . . ?
F1 B1 N2 109.2(2) . . ?
N1 B1 N2 107.32(18) . . ?
C11 C12 C13 108.4(2) . . ?
C11 C12 H12 125.8 . . ?
C13 C12 H12 125.8 . . ?
C18 C19 C14 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C3 C4 C5 111.3(2) . . ?
C3 C4 H4 124.4 . . ?
C5 C4 H4 124.4 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.58
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1941926'
loop_
_audit_author_name
_audit_author_address
S-YJ
; Hangzhou Normal University
China
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2019-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C136 H120 B8 F16 N16 S16'
_chemical_formula_weight         2882.08

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'
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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ' monoclinic'
_symmetry_space_group_name_H-M   'P 21/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                   14.9084(8)
_cell_length_b                   14.6028(8)
_cell_length_c                   20.2000(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.628(2)
_cell_angle_gamma                90.00
_cell_volume                     3337.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2730
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      28.91

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  '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            38763
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.65
_reflns_number_total             7723
_reflns_number_gt                5017
_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)+(0.0561P)²+0.1301P] 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         7723
_refine_ls_number_parameters     439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
S1 S 0.51252(5) 0.96520(3) 0.60876(4) 0.05766(15) Uani 1 1 d . . .
S2 S 0.24675(6) 1.00600(4) 0.62203(4) 0.06976(18) Uani 1 1 d . . .
F1 F 0.59314(9) 0.73648(7) 0.73048(8) 0.0689(4) Uani 1 1 d . . .
F2 F 0.47341(11) 0.73760(7) 0.58403(8) 0.0668(3) Uani 1 1 d . . .
N1 N 0.45134(12) 0.61536(9) 0.65325(9) 0.0402(3) Uani 1 1 d . . .
N2 N 0.38797(12) 0.77391(9) 0.64769(9) 0.0396(3) Uani 1 1 d . . .
C1 C 0.49795(17) 0.54195(12) 0.64570(11) 0.0458(4) Uani 1 1 d . . .
C2 C 0.44525(18) 0.46031(12) 0.64643(12) 0.0526(5) Uani 1 1 d . . .
C3 C 0.36614(17) 0.48641(12) 0.65620(12) 0.0513(5) Uani 1 1 d . . .
C4 C 0.36948(15) 0.58390(12) 0.66091(11) 0.0442(4) Uani 1 1 d . . .
C5 C 0.30452(16) 0.64450(13) 0.66579(12) 0.0485(5) Uani 1 1 d . . .
H5 H 0.2548 0.6224 0.6749 0.058 Uiso 1 1 calc R . .
C6 C 0.31031(15) 0.73906(13) 0.65751(12) 0.0460(4) Uani 1 1 d . . .
C7 C 0.24201(17) 0.80998(14) 0.65131(13) 0.0563(5) Uani 1 1 d . . .
H7 H 0.1843 0.8050 0.6561 0.068 Uiso 1 1 calc R . .
C8 C 0.27788(17) 0.88917(13) 0.63651(12) 0.0512(5) Uani 1 1 d . . .
C9 C 0.35287(18) 1.02260(13) 0.61195(13) 0.0550(5) Uani 1 1 d . . .
C10 C 0.3934(2) 1.10128(14) 0.59759(15) 0.0702(6) Uani 1 1 d . . .
H10 H 0.3650 1.1602 0.5913 0.084 Uiso 1 1 calc R . .
C11 C 0.4781(2) 1.08016(15) 0.59413(15) 0.0728(7) Uani 1 1 d . . .
H11 H 0.5146 1.1234 0.5848 0.087 Uiso 1 1 calc R . .
C12 C 0.41007(16) 0.94304(12) 0.61974(11) 0.0441(4) Uani 1 1 d . . .
C13 C 0.36725(15) 0.86556(11) 0.63483(11) 0.0404(4) Uani 1 1 d . . .
C14 C 0.2839(2) 0.42688(15) 0.65588(15) 0.0723(7) Uani 1 1 d . . .
H14A H 0.2302 0.3965 0.6006 0.108 Uiso 1 1 calc R . .
H14B H 0.2401 0.4640 0.6654 0.108 Uiso 1 1 calc R . .
H14C H 0.3288 0.3821 0.7015 0.108 Uiso 1 1 calc R . .
C15 C 0.5911(2) 0.54918(14) 0.63938(16) 0.0674(6) Uani 1 1 d . . .
H15A H 0.5552 0.5586 0.5796 0.101 Uiso 1 1 calc R . .
H15B H 0.6366 0.4937 0.6605 0.101 Uiso 1 1 calc R . .
H15C H 0.6419 0.5999 0.6739 0.101 Uiso 1 1 calc R . .
C16 C 0.4708(2) 0.36562(13) 0.63283(14) 0.0699(7) Uani 1 1 d . . .
H16A H 0.4535 0.3211 0.6587 0.084 Uiso 1 1 calc R . .
H16B H 0.5542 0.3609 0.6623 0.084 Uiso 1 1 calc R . .
C17 C 0.3990(3) 0.34345(16) 0.53738(16) 0.0993(10) Uani 1 1 d . . .
H17A H 0.3168 0.3400 0.5095 0.149 Uiso 1 1 calc R . .
H17B H 0.4242 0.2857 0.5317 0.149 Uiso 1 1 calc R . .
H17C H 0.4102 0.3906 0.5102 0.149 Uiso 1 1 calc R . .
B1 B 0.48064(18) 0.71724(13) 0.65416(13) 0.0410(5) Uani 1 1 d . . .
S3 S 0.23731(5) 0.87435(4) 0.87624(4) 0.06396(17) Uani 1 1 d . . .
S4 S -0.04177(5) 0.84591(4) 0.60712(4) 0.06010(16) Uani 1 1 d . . .
F3 F 0.03403(12) 0.62368(8) 0.60707(7) 0.0673(3) Uani 1 1 d . . .
F4 F -0.08901(10) 0.60673(8) 0.63499(8) 0.0669(3) Uani 1 1 d . . .
N3 N 0.11310(13) 0.64555(10) 0.75375(9) 0.0436(4) Uani 1 1 d . . .
N4 N 0.05866(13) 0.48993(10) 0.68847(9) 0.0416(3) Uani 1 1 d . . .
C18 C 0.12335(16) 0.73773(12) 0.76626(12) 0.0440(4) Uani 1 1 d . . .
C19 C 0.06854(17) 0.81823(13) 0.71498(13) 0.0476(4) Uani 1 1 d . . .
C20 C -0.0135(2) 0.96087(15) 0.63119(18) 0.0706(6) Uani 1 1 d . . .
H20 H -0.0550 1.0066 0.5891 0.085 Uiso 1 1 calc R . .
C21 C 0.0738(2) 0.97838(15) 0.71607(18) 0.0701(7) Uani 1 1 d . . .
H21 H 0.0995 1.0369 0.7396 0.084 Uiso 1 1 calc R . .
C22 C 0.12205(18) 0.89645(13) 0.76550(14) 0.0540(5) Uani 1 1 d . . .
C23 C 0.21607(17) 0.75724(14) 0.85486(13) 0.0511(5) Uani 1 1 d . . .
C24 C 0.26423(17) 0.67492(14) 0.89872(13) 0.0532(5) Uani 1 1 d . . .
H24 H 0.3264 0.6669 0.9581 0.064 Uiso 1 1 calc R . .
C25 C 0.20039(16) 0.60612(13) 0.83550(11) 0.0472(4) Uani 1 1 d . . .
C26 C 0.21519(16) 0.51079(13) 0.84244(12) 0.0473(4) Uani 1 1 d . . .
H26 H 0.2733 0.4853 0.8972 0.057 Uiso 1 1 calc R . .
C27 C 0.14799(16) 0.45414(12) 0.77232(11) 0.0426(4) Uani 1 1 d . . .
C28 C 0.14825(17) 0.35691(12) 0.76448(13) 0.0471(4) Uani 1 1 d . . .
C29 C 0.06046(17) 0.33515(12) 0.67852(13) 0.0485(5) Uani 1 1 d . . .
C30 C 0.00696(16) 0.41936(13) 0.63247(12) 0.0466(4) Uani 1 1 d . . .
C31 C 0.23263(19) 0.29303(14) 0.83937(14) 0.0621(6) Uani 1 1 d . . .
H31A H 0.1915 0.2384 0.8325 0.093 Uiso 1 1 calc R . .
H31B H 0.2643 0.3225 0.8932 0.093 Uiso 1 1 calc R . .
H31C H 0.2959 0.2774 0.8402 0.093 Uiso 1 1 calc R . .
C32 C 0.0235(2) 0.24251(14) 0.63630(16) 0.0654(6) Uani 1 1 d . . .
H32A H 0.0448 0.1970 0.6794 0.078 Uiso 1 1 calc R . .
H32B H -0.0618 0.2415 0.5906 0.078 Uiso 1 1 calc R . .
C33 C 0.0785(3) 0.21659(17) 0.59785(19) 0.0895(8) Uani 1 1 d . . .
H33A H 0.0602 0.2624 0.5565 0.134 Uiso 1 1 calc R . .
H33B H 0.0479 0.1585 0.5690 0.134 Uiso 1 1 calc R . .
H33C H 0.1627 0.2123 0.6435 0.134 Uiso 1 1 calc R . .
C34 C -0.0906(2) 0.43142(15) 0.53813(13) 0.0641(6) Uani 1 1 d . . .
H34A H -0.1363 0.4842 0.5283 0.096 Uiso 1 1 calc R . .
H34B H -0.1402 0.3781 0.5149 0.096 Uiso 1 1 calc R . .
H34C H -0.0589 0.4399 0.5097 0.096 Uiso 1 1 calc R . .
B2 B 0.02481(18) 0.59292(14) 0.66756(13) 0.0437(5) 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 C12 1.711(2) . ?
S1 C11 1.724(2) . ?
S2 C9 1.739(2) . ?
S2 C8 1.742(2) . ?
F1 B1 1.379(2) . ?
F2 B1 1.381(2) . ?
N1 C1 1.339(2) . ?
N1 C4 1.404(2) . ?
N1 B1 1.547(2) . ?
N2 C13 1.360(2) . ?
N2 C6 1.392(2) . ?
N2 B1 1.541(2) . ?
C1 C2 1.433(3) . ?
C1 C15 1.478(3) . ?
C2 C3 1.370(3) . ?
C2 C16 1.507(3) . ?
C3 C4 1.426(3) . ?
C3 C14 1.500(3) . ?
C4 C5 1.362(3) . ?
C5 C6 1.400(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.400(3) . ?
C7 C8 1.386(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.398(2) . ?
C9 C12 1.388(2) . ?
C9 C10 1.413(3) . ?
C10 C11 1.346(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.426(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.510(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
S3 C23 1.742(2) . ?
S3 C22 1.748(2) . ?
S4 C19 1.717(2) . ?
S4 C20 1.722(2) . ?
F3 B2 1.390(2) . ?
F4 B2 1.378(2) . ?
N3 C18 1.360(2) . ?
N3 C25 1.398(2) . ?
N3 B2 1.540(2) . ?
N4 C30 1.342(2) . ?
N4 C27 1.406(2) . ?
N4 B2 1.555(2) . ?
C18 C23 1.405(3) . ?
C18 C19 1.421(2) . ?
C19 C22 1.386(3) . ?
C20 C21 1.339(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.418(3) . ?
C21 H21 0.9300 . ?
C23 C24 1.385(3) . ?
C24 C25 1.401(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.402(3) . ?
C26 C27 1.359(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.429(2) . ?
C28 C29 1.367(3) . ?
C28 C31 1.504(2) . ?
C29 C30 1.431(2) . ?
C29 C32 1.500(3) . ?
C30 C34 1.473(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.499(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
C12 S1 C11 90.88(11) . . ?
C9 S2 C8 89.60(9) . . ?
C1 N1 C4 107.66(15) . . ?
C1 N1 B1 127.43(16) . . ?
C4 N1 B1 124.91(15) . . ?
C13 N2 C6 106.28(14) . . ?
C13 N2 B1 128.62(14) . . ?
C6 N2 B1 125.06(14) . . ?
N1 C1 C2 109.64(18) . . ?
N1 C1 C15 122.60(17) . . ?
C2 C1 C15 127.75(18) . . ?
C3 C2 C1 107.41(16) . . ?
C3 C2 C16 128.70(19) . . ?
C1 C2 C16 123.8(2) . . ?
C2 C3 C4 106.94(17) . . ?
C2 C3 C14 128.04(19) . . ?
C4 C3 C14 124.9(2) . . ?
C5 C4 N1 120.37(16) . . ?
C5 C4 C3 131.16(18) . . ?
N1 C4 C3 108.34(17) . . ?
C4 C5 C6 122.01(17) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
N2 C6 C7 109.94(16) . . ?
N2 C6 C5 119.94(16) . . ?
C7 C6 C5 129.98(18) . . ?
C8 C7 C6 106.03(17) . . ?
C8 C7 H7 127.0 . . ?
C6 C7 H7 127.0 . . ?
C7 C8 C13 107.89(17) . . ?
C7 C8 S2 139.05(16) . . ?
C13 C8 S2 113.04(15) . . ?
C12 C9 C10 113.0(2) . . ?
C12 C9 S2 114.12(15) . . ?
C10 C9 S2 132.87(17) . . ?
C11 C10 C9 111.4(2) . . ?
C11 C10 H10 124.3 . . ?
C9 C10 H10 124.3 . . ?
C10 C11 S1 113.51(18) . . ?
C10 C11 H11 123.2 . . ?
S1 C11 H11 123.2 . . ?
C9 C12 C13 111.15(18) . . ?
C9 C12 S1 111.18(15) . . ?
C13 C12 S1 137.67(14) . . ?
N2 C13 C8 109.85(16) . . ?
N2 C13 C12 138.07(16) . . ?
C8 C13 C12 112.08(16) . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C16 C17 112.10(18) . . ?
C2 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C2 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F1 B1 F2 109.18(16) . . ?
F1 B1 N2 110.86(15) . . ?
F2 B1 N2 109.29(15) . . ?
F1 B1 N1 109.73(15) . . ?
F2 B1 N1 111.21(15) . . ?
N2 B1 N1 106.54(14) . . ?
C23 S3 C22 89.73(10) . . ?
C19 S4 C20 90.87(11) . . ?
C18 N3 C25 106.43(15) . . ?
C18 N3 B2 127.89(15) . . ?
C25 N3 B2 125.68(15) . . ?
C30 N4 C27 107.67(14) . . ?
C30 N4 B2 127.39(15) . . ?
C27 N4 B2 124.89(15) . . ?
N3 C18 C23 109.62(16) . . ?
N3 C18 C19 137.87(18) . . ?
C23 C18 C19 112.50(17) . . ?
C22 C19 C18 111.27(18) . . ?
C22 C19 S4 110.89(15) . . ?
C18 C19 S4 137.78(16) . . ?
C21 C20 S4 113.75(18) . . ?
C21 C20 H20 123.1 . . ?
S4 C20 H20 123.1 . . ?
C20 C21 C22 111.4(2) . . ?
C20 C21 H21 124.3 . . ?
C22 C21 H21 124.3 . . ?
C19 C22 C21 113.1(2) . . ?
C19 C22 S3 113.89(15) . . ?
C21 C22 S3 133.02(18) . . ?
C24 C23 C18 108.02(17) . . ?
C24 C23 S3 139.38(16) . . ?
C18 C23 S3 112.60(15) . . ?
C23 C24 C25 106.13(17) . . ?
C23 C24 H24 126.9 . . ?
C25 C24 H24 126.9 . . ?
N3 C25 C24 109.80(17) . . ?
N3 C25 C26 119.47(16) . . ?
C24 C25 C26 130.66(17) . . ?
C27 C26 C25 122.62(16) . . ?
C27 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C26 C27 N4 120.42(16) . . ?
C26 C27 C28 131.84(17) . . ?
N4 C27 C28 107.74(16) . . ?
C29 C28 C27 107.59(16) . . ?
C29 C28 C31 127.97(18) . . ?
C27 C28 C31 124.44(18) . . ?
C28 C29 C30 107.05(16) . . ?
C28 C29 C32 128.70(18) . . ?
C30 C29 C32 124.25(18) . . ?
N4 C30 C29 109.94(16) . . ?
N4 C30 C34 122.70(17) . . ?
C29 C30 C34 127.36(18) . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C29 113.59(19) . . ?
C33 C32 H32A 108.8 . . ?
C29 C32 H32A 108.8 . . ?
C33 C32 H32B 108.8 . . ?
C29 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 C34 H34A 109.5 . . ?
C30 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C30 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
F4 B2 F3 109.21(16) . . ?
F4 B2 N3 110.30(15) . . ?
F3 B2 N3 109.38(16) . . ?
F4 B2 N4 110.62(16) . . ?
F3 B2 N4 110.56(15) . . ?
N3 B2 N4 106.76(14) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_mo190417b
_database_code_depnum_ccdc_archive 'CCDC 1935458'
loop_
_audit_author_name
_audit_author_address
tert-butyl
; Hangzhou Normal University
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-10-24 downloaded from the CCDC.
;
_audit_creation_date             2019-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 B F2 N2 S2'
_chemical_formula_sum            'C19 H19 B F2 N2 S2'
_chemical_formula_weight         388.29
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.326(2)
_cell_length_b                   7.2969(15)
_cell_length_c                   24.541(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.637(5)
_cell_angle_gamma                90
_cell_volume                     1817.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1869
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0750 before and 0.0604 after correction. The Ratio of minimum to maximum transmission is 0.8619. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0777
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14415
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.528
_diffrn_reflns_theta_min         1.689
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2464
_reflns_number_total             4591
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.0024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1369
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C9(H9)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 1.15647(7) 0.20676(11) 0.42612(3) 0.0601(2) Uani 1 1 d . . . . .
S2 S 0.99941(7) 0.73793(9) 0.42226(3) 0.0571(2) Uani 1 1 d . . . . .
F1 F 0.70413(13) 0.5631(2) 0.32967(6) 0.0531(4) Uani 1 1 d . . . . .
F2 F 0.84680(14) 0.72205(18) 0.28816(6) 0.0531(4) Uani 1 1 d . . . . .
N1 N 0.89366(18) 0.4059(3) 0.30999(8) 0.0378(5) Uani 1 1 d . . . . .
N2 N 0.70889(18) 0.4908(3) 0.23411(8) 0.0362(5) Uani 1 1 d . . . . .
C1 C 0.9820(2) 0.3988(3) 0.35832(10) 0.0400(6) Uani 1 1 d . . . . .
C2 C 1.0270(2) 0.5169(3) 0.40364(10) 0.0438(6) Uani 1 1 d . . . . .
C3 C 1.1118(3) 0.7108(4) 0.48334(12) 0.0639(8) Uani 1 1 d . . . . .
H3 H 1.1320 0.8034 0.5096 0.077 Uiso 1 1 calc R . . . .
C4 C 1.1671(3) 0.5441(4) 0.48945(12) 0.0610(8) Uani 1 1 d . . . . .
H4 H 1.2285 0.5077 0.5202 0.073 Uiso 1 1 calc R . . . .
C5 C 1.1204(2) 0.4306(4) 0.44338(11) 0.0498(7) Uani 1 1 d . . . . .
C6 C 1.0445(2) 0.2277(3) 0.36376(11) 0.0466(6) Uani 1 1 d . . . . .
C7 C 0.9958(2) 0.1250(4) 0.31741(11) 0.0469(7) Uani 1 1 d . . . . .
H7 H 1.0194 0.0061 0.3098 0.056 Uiso 1 1 calc R . . . .
C8 C 0.9024(2) 0.2379(3) 0.28387(10) 0.0405(6) Uani 1 1 d . . . . .
C9 C 0.8215(2) 0.2024(3) 0.23300(11) 0.0422(6) Uani 1 1 d . . . . .
H9 H 0.8306 0.0916 0.2153 0.051 Uiso 1 1 calc R . . . .
C10 C 0.7283(2) 0.3263(3) 0.20800(10) 0.0367(5) Uani 1 1 d . . . . .
C11 C 0.6344(2) 0.3153(3) 0.15774(10) 0.0402(6) Uani 1 1 d . . . . .
C12 C 0.5555(2) 0.4702(3) 0.15406(10) 0.0388(6) Uani 1 1 d . . . . .
C13 C 0.6070(2) 0.5776(3) 0.20265(9) 0.0376(6) Uani 1 1 d . . . . .
C14 C 0.6346(3) 0.1556(4) 0.11928(12) 0.0673(9) Uani 1 1 d . . . . .
H14A H 0.6557 0.1974 0.0849 0.101 Uiso 1 1 calc GR . . . .
H14B H 0.5491 0.0994 0.1125 0.101 Uiso 1 1 calc GR . . . .
H14C H 0.6992 0.0677 0.1359 0.101 Uiso 1 1 calc GR . . . .
C15 C 0.4370(2) 0.5264(3) 0.11018(10) 0.0429(6) Uani 1 1 d . . . . .
C16 C 0.3958(3) 0.3764(5) 0.06667(13) 0.0837(11) Uani 1 1 d . . . . .
H16A H 0.4652 0.3571 0.0461 0.126 Uiso 1 1 calc GR . . . .
H16B H 0.3172 0.4136 0.0418 0.126 Uiso 1 1 calc GR . . . .
H16C H 0.3793 0.2646 0.0848 0.126 Uiso 1 1 calc GR . . . .
C17 C 0.4687(3) 0.6990(5) 0.08036(13) 0.0780(10) Uani 1 1 d . . . . .
H17A H 0.4838 0.7989 0.1062 0.117 Uiso 1 1 calc GR . . . .
H17B H 0.3960 0.7281 0.0512 0.117 Uiso 1 1 calc GR . . . .
H17C H 0.5463 0.6788 0.0648 0.117 Uiso 1 1 calc GR . . . .
C18 C 0.3163(2) 0.5588(4) 0.13668(12) 0.0621(8) Uani 1 1 d . . . . .
H18A H 0.2915 0.4460 0.1521 0.093 Uiso 1 1 calc GR . . . .
H18B H 0.2446 0.6021 0.1091 0.093 Uiso 1 1 calc GR . . . .
H18C H 0.3369 0.6486 0.1656 0.093 Uiso 1 1 calc GR . . . .
C19 C 0.5630(3) 0.7572(3) 0.22110(11) 0.0542(7) Uani 1 1 d . . . . .
H19A H 0.5087 0.7377 0.2484 0.081 Uiso 1 1 calc GR . . . .
H19B H 0.5133 0.8210 0.1899 0.081 Uiso 1 1 calc GR . . . .
H19C H 0.6386 0.8289 0.2370 0.081 Uiso 1 1 calc GR . . . .
B1 B 0.7881(3) 0.5537(4) 0.29160(12) 0.0387(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 C5 1.745(3) . ?
S1 C6 1.746(3) . ?
S2 C2 1.714(3) . ?
S2 C3 1.729(3) . ?
F1 B1 1.388(3) . ?
F2 B1 1.379(3) . ?
N1 C1 1.357(3) . ?
N1 C8 1.394(3) . ?
N1 B1 1.541(3) . ?
N2 C10 1.393(3) . ?
N2 C13 1.343(3) . ?
N2 B1 1.563(3) . ?
C1 C2 1.416(3) . ?
C1 C6 1.401(3) . ?
C2 C5 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.340(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.413(4) . ?
C6 C7 1.377(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.412(3) . ?
C8 C9 1.392(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(3) . ?
C10 C11 1.423(3) . ?
C11 C12 1.386(3) . ?
C11 C14 1.500(3) . ?
C12 C13 1.444(3) . ?
C12 C15 1.529(3) . ?
C13 C19 1.485(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.533(4) . ?
C15 C17 1.522(4) . ?
C15 C18 1.527(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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 . ?

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
C5 S1 C6 89.69(12) . . ?
C2 S2 C3 90.31(14) . . ?
C1 N1 C8 106.17(19) . . ?
C1 N1 B1 127.42(19) . . ?
C8 N1 B1 125.67(19) . . ?
C10 N2 B1 124.94(19) . . ?
C13 N2 C10 107.81(19) . . ?
C13 N2 B1 127.2(2) . . ?
N1 C1 C2 137.2(2) . . ?
N1 C1 C6 109.9(2) . . ?
C6 C1 C2 112.9(2) . . ?
C1 C2 S2 137.35(19) . . ?
C5 C2 S2 111.5(2) . . ?
C5 C2 C1 111.1(2) . . ?
S2 C3 H3 123.1 . . ?
C4 C3 S2 113.9(2) . . ?
C4 C3 H3 123.1 . . ?
C3 C4 H4 124.2 . . ?
C3 C4 C5 111.5(2) . . ?
C5 C4 H4 124.2 . . ?
C2 C5 S1 113.9(2) . . ?
C2 C5 C4 112.7(3) . . ?
C4 C5 S1 133.4(2) . . ?
C1 C6 S1 112.4(2) . . ?
C7 C6 S1 139.3(2) . . ?
C7 C6 C1 108.3(2) . . ?
C6 C7 H7 127.2 . . ?
C6 C7 C8 105.7(2) . . ?
C8 C7 H7 127.2 . . ?
N1 C8 C7 109.9(2) . . ?
C9 C8 N1 119.8(2) . . ?
C9 C8 C7 130.2(2) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.0(2) . . ?
C10 C9 H9 119.0 . . ?
N2 C10 C11 108.3(2) . . ?
C9 C10 N2 120.6(2) . . ?
C9 C10 C11 131.0(2) . . ?
C10 C11 C14 120.6(2) . . ?
C12 C11 C10 108.0(2) . . ?
C12 C11 C14 131.4(2) . . ?
C11 C12 C13 105.4(2) . . ?
C11 C12 C15 130.4(2) . . ?
C13 C12 C15 124.1(2) . . ?
N2 C13 C12 110.4(2) . . ?
N2 C13 C19 119.5(2) . . ?
C12 C13 C19 130.1(2) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C16 112.4(2) . . ?
C17 C15 C12 110.2(2) . . ?
C17 C15 C16 108.2(2) . . ?
C17 C15 C18 110.0(2) . . ?
C18 C15 C12 110.6(2) . . ?
C18 C15 C16 105.3(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 B1 N1 109.5(2) . . ?
F1 B1 N2 109.5(2) . . ?
F2 B1 F1 109.5(2) . . ?
F2 B1 N1 110.2(2) . . ?
F2 B1 N2 111.6(2) . . ?
N1 B1 N2 106.41(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
