# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1976346'
loop_
_audit_author_name
_audit_author_address
'Shun-Yi Wang'
;Soochow University
China
;
_audit_update_record             
;
2020-01-09 deposited with the CCDC.	2020-08-27 downloaded from the CCDC.
;
_audit_creation_date             2018-06-08
_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         'C28 H21 F N2 O2 S Se'
_chemical_formula_sum            'C28 H21 F N2 O2 S Se'
_chemical_formula_weight         547.49
_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'
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'
O O 0.0106 0.0060 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.215(3)
_cell_length_b                   11.927(2)
_cell_length_c                   15.344(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.15(3)
_cell_angle_gamma                90
_cell_volume                     2372.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11441
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.9080
_cell_measurement_theta_min      2.1785
_shelx_estimated_absorpt_T_max   0.548
_shelx_estimated_absorpt_T_min   0.427
_exptl_absorpt_coefficient_mu    1.708
_exptl_absorpt_correction_T_max  34.9080
_exptl_absorpt_correction_T_min  2.1785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.7065
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12186
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.864
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn 724+'
_diffrn_measurement_method       'ω scan'
_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                4535
_reflns_number_total             4819
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+3.2857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0955
_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. Others
 Sof(H17)=Sof(F1A)=1-FVAR(1)
 Sof(H21)=Sof(F1)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C26(H26), C27(H27)
3.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.4714(2) 0.2201(2) 1.02630(18) 0.0250(6) Uani 1 1 d . . . . .
C2 C 0.3884(2) 0.1815(2) 1.0606(2) 0.0296(6) Uani 1 1 d . . . . .
H2 H 0.3907 0.1094 1.0872 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3019(2) 0.2484(3) 1.0560(2) 0.0376(7) Uani 1 1 d . . . . .
H3 H 0.2443 0.2211 1.0782 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2986(2) 0.3541(3) 1.0195(2) 0.0413(8) Uani 1 1 d . . . . .
H4 H 0.2392 0.3997 1.0167 0.050 Uiso 1 1 calc R . . . .
C5 C 0.3821(3) 0.3930(3) 0.9871(2) 0.0458(8) Uani 1 1 d . . . . .
H5 H 0.3806 0.4664 0.9629 0.055 Uiso 1 1 calc R . . . .
C6 C 0.4687(2) 0.3261(3) 0.9894(2) 0.0363(7) Uani 1 1 d . . . . .
H6 H 0.5256 0.3530 0.9659 0.044 Uiso 1 1 calc R . . . .
C7 C 0.74449(18) 0.2500(2) 0.97642(16) 0.0182(5) Uani 1 1 d . . . . .
C8 C 0.69492(18) 0.2231(2) 1.04445(17) 0.0203(5) Uani 1 1 d . . . . .
C9 C 0.72550(19) 0.2708(2) 1.13130(17) 0.0204(5) Uani 1 1 d . . . . .
C10 C 0.6830(2) 0.2427(2) 1.20561(18) 0.0257(6) Uani 1 1 d . . . . .
H10 H 0.6282 0.1901 1.1997 0.031 Uiso 1 1 calc R . . . .
C11 C 0.7202(2) 0.2907(3) 1.28629(19) 0.0308(6) Uani 1 1 d . . . . .
H11 H 0.6917 0.2693 1.3361 0.037 Uiso 1 1 calc R . . . .
C12 C 0.7994(2) 0.3708(3) 1.29746(19) 0.0320(6) Uani 1 1 d . . . . .
H12 H 0.8236 0.4032 1.3542 0.038 Uiso 1 1 calc R . . . .
C13 C 0.8418(2) 0.4023(2) 1.22639(19) 0.0283(6) Uani 1 1 d . . . . .
H13 H 0.8946 0.4575 1.2333 0.034 Uiso 1 1 calc R . . . .
C14 C 0.80618(19) 0.3516(2) 1.14236(17) 0.0208(5) Uani 1 1 d . . . . .
C15 C 0.85100(19) 0.3799(2) 1.06975(17) 0.0201(5) Uani 1 1 d . . . . .
H15 H 0.9028 0.4362 1.0768 0.024 Uiso 1 1 calc R . . . .
C16 C 0.71835(19) 0.2014(2) 0.88530(17) 0.0211(5) Uani 1 1 d . . . . .
C17 C 0.7331(2) 0.0887(2) 0.87021(19) 0.0278(6) Uani 1 1 d . . . . .
H17 H 0.7647 0.0429 0.9185 0.033 Uiso 0.375(5) 1 calc R . P A 2
C18 C 0.7036(2) 0.0404(3) 0.7872(2) 0.0344(7) Uani 1 1 d . . . . .
H18 H 0.7148 -0.0372 0.7789 0.041 Uiso 1 1 calc R . . . .
C19 C 0.6575(3) 0.1065(3) 0.7167(2) 0.0387(8) Uani 1 1 d . . . . .
H19 H 0.6361 0.0742 0.6595 0.046 Uiso 1 1 calc R . . . .
C20 C 0.6428(2) 0.2190(3) 0.7293(2) 0.0368(7) Uani 1 1 d . . . . .
H20 H 0.6115 0.2648 0.6809 0.044 Uiso 1 1 calc R . . . .
C21 C 0.6740(2) 0.2653(3) 0.81302(19) 0.0295(6) Uani 1 1 d . . . . .
H21 H 0.6645 0.3433 0.8209 0.035 Uiso 0.625(5) 1 calc R . P A 1
C22 C 0.99190(19) 0.1946(2) 0.88078(17) 0.0203(5) Uani 1 1 d . . . . .
C23 C 1.0452(2) 0.1080(2) 0.92918(19) 0.0284(6) Uani 1 1 d . . . . .
H23 H 1.0679 0.1148 0.9916 0.034 Uiso 1 1 calc R . . . .
C24 C 1.0650(2) 0.0109(2) 0.8853(2) 0.0329(7) Uani 1 1 d . . . . .
H24 H 1.1009 -0.0492 0.9183 0.040 Uiso 1 1 calc R . . . .
C25 C 1.0334(2) 0.0001(2) 0.7942(2) 0.0302(6) Uani 1 1 d . . . . .
C26 C 0.9743(2) 0.0846(2) 0.74786(19) 0.0278(6) Uani 1 1 d . . . . .
H26 H 0.9476 0.0757 0.6862 0.033 Uiso 1 1 calc R . . . .
C27 C 0.9536(2) 0.1821(2) 0.79026(18) 0.0241(5) Uani 1 1 d . . . . .
H27 H 0.9136 0.2400 0.7578 0.029 Uiso 1 1 calc R . . . .
C28 C 1.0683(3) -0.0992(3) 0.7463(3) 0.0462(9) Uani 1 1 d . . . . .
H28A H 1.1377 -0.0850 0.7351 0.069 Uiso 1 1 calc GR . . . .
H28B H 1.0205 -0.1104 0.6896 0.069 Uiso 1 1 calc GR . . . .
H28C H 1.0692 -0.1665 0.7830 0.069 Uiso 1 1 calc GR . . . .
F1 F 0.7727(2) 0.0263(2) 0.93593(16) 0.0284(8) Uani 0.625(5) 1 d . . P A 1
F1A F 0.6575(3) 0.3657(3) 0.8295(3) 0.0324(14) Uani 0.375(5) 1 d . . P A 2
N1 N 0.82301(16) 0.33032(17) 0.99158(14) 0.0184(4) Uani 1 1 d . . . . .
N2 N 0.86709(16) 0.36598(18) 0.91942(14) 0.0215(5) Uani 1 1 d . . . . .
O1 O 1.03755(15) 0.31724(19) 1.02058(13) 0.0352(5) Uani 1 1 d . . . . .
O2 O 1.02732(17) 0.40354(17) 0.87235(15) 0.0369(5) Uani 1 1 d . . . . .
S1 S 0.98478(5) 0.32832(5) 0.92944(4) 0.02300(15) Uani 1 1 d . . . . .
Se1 Se 0.58286(2) 0.11766(2) 1.02202(2) 0.02632(10) 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
C1 C2 1.385(4) . ?
C1 C6 1.382(4) . ?
C1 Se1 1.925(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(3) . ?
C7 C16 1.491(3) . ?
C7 N1 1.398(3) . ?
C8 C9 1.434(4) . ?
C8 Se1 1.922(2) . ?
C9 C10 1.405(4) . ?
C9 C14 1.423(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.366(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.403(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.419(4) . ?
C14 C15 1.400(4) . ?
C15 H15 0.9500 . ?
C15 N1 1.324(3) . ?
C16 C17 1.385(4) . ?
C16 C21 1.380(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(4) . ?
C17 F1 1.281(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.375(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(4) . ?
C21 H21 0.9500 . ?
C21 F1A 1.251(5) . ?
C22 C23 1.382(4) . ?
C22 C27 1.391(4) . ?
C22 S1 1.772(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(4) . ?
C25 C26 1.384(4) . ?
C25 C28 1.513(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(4) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1 N2 1.413(3) . ?
N2 S1 1.598(2) . ?
O1 S1 1.443(2) . ?
O2 S1 1.442(2) . ?

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
C2 C1 Se1 118.0(2) . . ?
C6 C1 C2 120.0(3) . . ?
C6 C1 Se1 121.7(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C16 124.3(2) . . ?
C8 C7 N1 118.8(2) . . ?
N1 C7 C16 116.9(2) . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 Se1 118.76(19) . . ?
C9 C8 Se1 119.68(18) . . ?
C10 C9 C8 125.0(2) . . ?
C10 C9 C14 118.2(2) . . ?
C14 C9 C8 116.7(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.7(3) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 120.4(2) . . ?
C15 C14 C9 119.4(2) . . ?
C15 C14 C13 120.2(2) . . ?
C14 C15 H15 119.1 . . ?
N1 C15 C14 121.7(2) . . ?
N1 C15 H15 119.1 . . ?
C17 C16 C7 121.3(2) . . ?
C17 C16 C21 117.0(2) . . ?
C21 C16 C7 121.6(2) . . ?
C16 C17 H17 118.9 . . ?
C16 C17 C18 122.3(3) . . ?
C18 C17 H17 118.9 . . ?
F1 C17 C16 118.8(3) . . ?
F1 C17 C18 118.9(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 C20 121.9(3) . . ?
C16 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
F1A C21 C16 115.4(3) . . ?
F1A C21 C20 122.4(3) . . ?
C23 C22 C27 120.4(2) . . ?
C23 C22 S1 120.6(2) . . ?
C27 C22 S1 118.6(2) . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.1(3) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.2(3) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 118.7(3) . . ?
C24 C25 C28 120.2(3) . . ?
C26 C25 C28 121.0(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.9(3) . . ?
C27 C26 H26 119.6 . . ?
C22 C27 H27 120.3 . . ?
C26 C27 C22 119.5(3) . . ?
C26 C27 H27 120.3 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C7 N1 N2 118.8(2) . . ?
C15 N1 C7 121.7(2) . . ?
C15 N1 N2 119.3(2) . . ?
N1 N2 S1 112.41(17) . . ?
N2 S1 C22 110.04(12) . . ?
O1 S1 C22 105.72(13) . . ?
O1 S1 N2 113.46(12) . . ?
O2 S1 C22 104.22(12) . . ?
O2 S1 N2 104.67(13) . . ?
O2 S1 O1 118.27(14) . . ?
C8 Se1 C1 98.42(11) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
