# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_3secf3
_database_code_depnum_ccdc_archive 'CCDC 2084131'
loop_
_audit_author_name
_audit_author_address
'hui wang'
;FuZhou University
China
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_audit_creation_date             2021-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        P1
_chemical_formula_moiety         'C22 H15 Br F3 N O2 S Se'
_chemical_formula_sum            'C22 H15 Br F3 N O2 S Se'
_chemical_formula_weight         573.28
_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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.0368(4)
_cell_length_b                   9.7879(5)
_cell_length_c                   12.8089(6)
_cell_angle_alpha                72.001(2)
_cell_angle_beta                 83.060(2)
_cell_angle_gamma                79.877(2)
_cell_volume                     1058.06(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.616
_cell_measurement_theta_min      3.638
_exptl_absorpt_coefficient_mu    5.960
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21152
_diffrn_reflns_theta_full        66.61
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_min         3.64
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3574
_reflns_number_total             3696
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00147(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0272P)²+0.9950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0627
_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. 
;
_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:
 C17(H17), C13(H13), C10(H10), C4(H4), C16(H16), C20(H20), C7(H7), C11(H11),
 C19(H19), C14(H14), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.82247(2) 0.71084(3) 0.91882(2) 0.02964(9) Uani 1 d . . .
Br1 Br 1.09142(3) 0.78351(3) 0.38956(2) 0.03767(10) Uani 1 d . . .
S1 S 0.34968(6) 0.71800(5) 0.66640(4) 0.02089(12) Uani 1 d . . .
O2 O 0.19960(17) 0.78558(16) 0.68488(12) 0.0267(3) Uani 1 d . . .
O1 O 0.43838(18) 0.77577(17) 0.56803(12) 0.0278(3) Uani 1 d . . .
F1 F 0.7365(2) 1.00393(18) 0.82073(14) 0.0569(5) Uani 1 d . . .
F3 F 0.6843(2) 0.94177(19) 0.99212(15) 0.0645(5) Uani 1 d . . .
N1 N 0.44428(19) 0.72245(19) 0.77074(13) 0.0195(4) Uani 1 d . . .
F2 F 0.9133(2) 0.9537(2) 0.9292(2) 0.0824(7) Uani 1 d . . .
C3 C 0.4947(2) 0.6977(2) 0.94558(16) 0.0197(4) Uani 1 d . . .
C1 C 0.6005(2) 0.7233(2) 0.77028(16) 0.0195(4) Uani 1 d . . .
C8 C 0.3790(2) 0.7044(2) 0.87988(16) 0.0195(4) Uani 1 d . . .
C12 C 0.9357(2) 0.7646(3) 0.50502(17) 0.0246(4) Uani 1 d . . .
C9 C 0.7101(2) 0.7386(2) 0.67315(16) 0.0203(4) Uani 1 d . . .
C17 C 0.4670(3) 0.3057(3) 0.66202(18) 0.0276(5) Uani 1 d . . .
H17 H 0.5489 0.2505 0.6357 0.033 Uiso 1 calc . . R
C13 C 0.8369(3) 0.8868(2) 0.51215(18) 0.0284(5) Uani 1 d . . .
H13 H 0.8462 0.9768 0.4613 0.034 Uiso 1 calc . . R
C15 C 0.3473(2) 0.5328(2) 0.68645(16) 0.0212(4) Uani 1 d . . .
C10 C 0.8131(3) 0.6179(2) 0.66422(17) 0.0251(5) Uani 1 d . . .
H10 H 0.8060 0.5280 0.7157 0.030 Uiso 1 calc . . R
C4 C 0.4623(2) 0.6875(2) 1.05723(17) 0.0236(4) Uani 1 d . . .
H4 H 0.5382 0.6841 1.1014 0.028 Uiso 1 calc . . R
C2 C 0.6306(2) 0.7094(2) 0.87515(17) 0.0211(4) Uani 1 d . . .
C16 C 0.4700(3) 0.4516(2) 0.64586(17) 0.0254(5) Uani 1 d . . .
H16 H 0.5526 0.4947 0.6085 0.030 Uiso 1 calc . . R
C20 C 0.2227(2) 0.4707(2) 0.74120(18) 0.0257(5) Uani 1 d . . .
H20 H 0.1410 0.5260 0.7676 0.031 Uiso 1 calc . . R
C7 C 0.2314(2) 0.6970(3) 0.92317(18) 0.0269(5) Uani 1 d . . .
H7 H 0.1553 0.6995 0.8796 0.032 Uiso 1 calc . . R
C11 C 0.9259(3) 0.6300(2) 0.57994(18) 0.0267(5) Uani 1 d . . .
H11 H 0.9937 0.5491 0.5739 0.032 Uiso 1 calc . . R
C19 C 0.2219(3) 0.3243(3) 0.75590(19) 0.0283(5) Uani 1 d . . .
H19 H 0.1386 0.2817 0.7925 0.034 Uiso 1 calc . . R
C14 C 0.7236(2) 0.8729(2) 0.59636(18) 0.0270(5) Uani 1 d . . .
H14 H 0.6559 0.9542 0.6017 0.032 Uiso 1 calc . . R
C18 C 0.3435(3) 0.2401(2) 0.71697(18) 0.0272(5) Uani 1 d . . .
C5 C 0.3156(3) 0.6828(2) 1.09976(17) 0.0266(5) Uani 1 d . . .
H5 H 0.2915 0.6775 1.1734 0.032 Uiso 1 calc . . R
C6 C 0.2021(3) 0.6857(3) 1.03369(19) 0.0296(5) Uani 1 d . . .
H6 H 0.1041 0.6800 1.0650 0.036 Uiso 1 calc . . R
C22 C 0.7872(3) 0.9151(3) 0.9145(2) 0.0373(6) Uani 1 d . . .
C21 C 0.3432(3) 0.0808(3) 0.7349(2) 0.0388(6) Uani 1 d . . .
H21A H 0.3781 0.0573 0.6679 0.058 Uiso 1 calc . . GR
H21B H 0.2426 0.0585 0.7567 0.058 Uiso 1 calc . . GR
H21C H 0.4086 0.0251 0.7917 0.058 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C2 1.889(2) . ?
Se1 C22 1.953(3) . ?
Br1 C12 1.903(2) . ?
S1 O2 1.4272(16) . ?
S1 O1 1.4230(16) . ?
S1 N1 1.6864(17) . ?
S1 C15 1.754(2) . ?
F1 C22 1.325(3) . ?
F3 C22 1.331(3) . ?
N1 C1 1.413(3) . ?
N1 C8 1.420(3) . ?
F2 C22 1.313(3) . ?
C3 C8 1.400(3) . ?
C3 C4 1.401(3) . ?
C3 C2 1.433(3) . ?
C1 C9 1.480(3) . ?
C1 C2 1.363(3) . ?
C8 C7 1.386(3) . ?
C12 C13 1.381(3) . ?
C12 C11 1.380(3) . ?
C9 C10 1.395(3) . ?
C9 C14 1.393(3) . ?
C17 C16 1.383(3) . ?
C17 C18 1.392(3) . ?
C13 C14 1.386(3) . ?
C15 C16 1.392(3) . ?
C15 C20 1.384(3) . ?
C10 C11 1.384(3) . ?
C4 C5 1.374(3) . ?
C20 C19 1.387(3) . ?
C7 C6 1.382(3) . ?
C19 C18 1.392(3) . ?
C18 C21 1.504(3) . ?
C5 C6 1.398(3) . ?

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 Se1 C22 95.70(10) . . ?
O2 S1 N1 105.51(9) . . ?
O2 S1 C15 108.68(10) . . ?
O1 S1 O2 120.79(9) . . ?
O1 S1 N1 106.14(9) . . ?
O1 S1 C15 109.78(10) . . ?
N1 S1 C15 104.67(9) . . ?
C1 N1 S1 127.26(14) . . ?
C1 N1 C8 108.72(16) . . ?
C8 N1 S1 123.45(14) . . ?
C8 C3 C4 120.18(19) . . ?
C8 C3 C2 106.88(17) . . ?
C4 C3 C2 132.89(19) . . ?
N1 C1 C9 125.99(17) . . ?
C2 C1 N1 107.34(17) . . ?
C2 C1 C9 126.66(19) . . ?
C3 C8 N1 107.22(17) . . ?
C7 C8 N1 131.19(19) . . ?
C7 C8 C3 121.57(19) . . ?
C13 C12 Br1 118.89(17) . . ?
C11 C12 Br1 119.19(16) . . ?
C11 C12 C13 121.9(2) . . ?
C10 C9 C1 119.03(18) . . ?
C14 C9 C1 121.81(18) . . ?
C14 C9 C10 118.82(19) . . ?
C16 C17 C18 121.1(2) . . ?
C12 C13 C14 118.8(2) . . ?
C16 C15 S1 119.36(17) . . ?
C20 C15 S1 119.35(16) . . ?
C20 C15 C16 121.3(2) . . ?
C11 C10 C9 121.0(2) . . ?
C5 C4 C3 118.3(2) . . ?
C3 C2 Se1 125.56(15) . . ?
C1 C2 Se1 124.60(16) . . ?
C1 C2 C3 109.82(18) . . ?
C17 C16 C15 118.9(2) . . ?
C15 C20 C19 118.8(2) . . ?
C6 C7 C8 117.3(2) . . ?
C12 C11 C10 118.7(2) . . ?
C20 C19 C18 121.3(2) . . ?
C13 C14 C9 120.8(2) . . ?
C17 C18 C19 118.7(2) . . ?
C17 C18 C21 120.3(2) . . ?
C19 C18 C21 121.0(2) . . ?
C4 C5 C6 120.8(2) . . ?
C7 C6 C5 121.8(2) . . ?
F1 C22 Se1 113.53(18) . . ?
F1 C22 F3 104.9(2) . . ?
F3 C22 Se1 112.63(18) . . ?
F2 C22 Se1 109.50(19) . . ?
F2 C22 F1 108.1(2) . . ?
F2 C22 F3 107.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
