# 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_3b_0m_b_tw
_database_code_depnum_ccdc_archive 'CCDC 2191725'
loop_
_audit_author_name
_audit_author_address
'Zhengkai Chen'
;Zhejiang Sci Tech University
China
;
_audit_update_record             
;
2022-07-21 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 F3 N O0 Se'
_chemical_formula_weight         442.33

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'
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'
Se Se -0.0929 2.2259 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   5.759(2)
_cell_length_b                   16.083(6)
_cell_length_c                   10.639(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.483(4)
_cell_angle_gamma                90
_cell_volume                     977.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1993
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.79

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.956
_shelx_estimated_absorpt_T_min   0.708
_shelx_estimated_absorpt_T_max   0.745
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3837
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         27.609
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             3837
_reflns_number_gt                3067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_max     0.837
_reflns_Friedel_fraction_full    0.872

_reflns_special_details          
;
 _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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1001 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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_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
Se1 Se 0.04429(11) 0.57906(6) 0.58768(6) 0.0446(2) Uani 1 1 d . . . . .
F1 F 0.2664(11) 0.7225(3) 0.7789(5) 0.0715(15) Uani 1 1 d . . . . .
F2 F -0.0007(11) 0.6538(4) 0.8508(6) 0.0793(17) Uani 1 1 d . . . . .
F3 F 0.3056(13) 0.6904(4) 0.9736(5) 0.090(2) Uani 1 1 d . . . . .
N1 N 0.5136(12) 0.5581(4) 0.9198(5) 0.050(2) Uani 1 1 d . . . . .
C1 C 0.2940(12) 0.5376(4) 0.7123(6) 0.0360(14) Uani 1 1 d . . . . .
C2 C 0.3507(11) 0.5814(7) 0.8289(5) 0.0422(13) Uani 1 1 d . . . . .
C3 C 0.6364(14) 0.4886(5) 0.9017(7) 0.0474(18) Uani 1 1 d . . . . .
C4 C 0.6006(13) 0.4409(5) 0.7879(6) 0.0396(15) Uani 1 1 d . . . . .
C5 C 0.4194(11) 0.4677(4) 0.6914(6) 0.0330(14) Uani 1 1 d . . . . .
C6 C 0.3762(11) 0.4188(4) 0.5714(6) 0.0353(14) Uani 1 1 d . . . . .
C7 C 0.1729(13) 0.3717(5) 0.5460(7) 0.0456(17) Uani 1 1 d . . . . .
H7 H 0.066097 0.370798 0.604494 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1268(15) 0.3258(5) 0.4343(8) 0.055(2) Uani 1 1 d . . . . .
H8 H -0.010723 0.295155 0.417635 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2868(17) 0.3264(6) 0.3493(8) 0.059(2) Uani 1 1 d . . . . .
H9 H 0.257658 0.295862 0.274750 0.071 Uiso 1 1 calc R U . . .
C10 C 0.4935(16) 0.3727(6) 0.3741(8) 0.055(2) Uani 1 1 d . . . . .
H10 H 0.603687 0.372224 0.317474 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5311(13) 0.4193(5) 0.4844(7) 0.0434(17) Uani 1 1 d . . . . .
H11 H 0.665413 0.451824 0.499600 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7430(13) 0.3698(5) 0.7777(7) 0.0419(16) Uani 1 1 d . . . . .
H12 H 0.717015 0.337331 0.704897 0.050 Uiso 1 1 calc R U . . .
C13 C 0.9157(15) 0.3477(6) 0.8708(8) 0.0508(19) Uani 1 1 d . . . . .
C14 C 0.9510(17) 0.3973(6) 0.9825(8) 0.066(3) Uani 1 1 d . . . . .
H14 H 1.069773 0.383230 1.046723 0.079 Uiso 1 1 calc R U . . .
C15 C 0.8160(18) 0.4643(6) 0.9972(8) 0.068(3) Uani 1 1 d . . . . .
H15 H 0.842158 0.494882 1.071840 0.081 Uiso 1 1 calc R U . . .
C16 C 1.0741(18) 0.2757(6) 0.8572(9) 0.063(2) Uani 1 1 d . . . . .
H16A H 1.220802 0.295617 0.835346 0.095 Uiso 1 1 calc R U . . .
H16B H 1.002834 0.239394 0.791672 0.095 Uiso 1 1 calc R U . . .
H16C H 1.100634 0.245833 0.935907 0.095 Uiso 1 1 calc R U . . .
C17 C 0.2268(13) 0.5968(4) 0.4496(6) 0.0396(18) Uani 1 1 d . . . . .
C18 C 0.1594(15) 0.5587(5) 0.3336(7) 0.054(2) Uani 1 1 d . . . . .
H18 H 0.028818 0.524146 0.322710 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2862(17) 0.5722(9) 0.2354(7) 0.068(2) Uani 1 1 d . . . . .
H19 H 0.237590 0.548205 0.156828 0.081 Uiso 1 1 calc R U . . .
C20 C 0.4858(18) 0.6210(6) 0.2511(8) 0.060(2) Uani 1 1 d . . . . .
H20 H 0.573946 0.628281 0.184706 0.072 Uiso 1 1 calc R U . . .
C21 C 0.5524(16) 0.6588(6) 0.3673(9) 0.057(2) Uani 1 1 d . . . . .
H21 H 0.685516 0.692073 0.378895 0.069 Uiso 1 1 calc R U . . .
C22 C 0.4217(15) 0.6471(6) 0.4657(8) 0.052(2) Uani 1 1 d . . . . .
H22 H 0.465506 0.673265 0.543058 0.063 Uiso 1 1 calc R U . . .
C23 C 0.2337(18) 0.6612(6) 0.8587(7) 0.055(2) 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
Se1 C17 1.935(7) . ?
Se1 C1 1.943(7) . ?
F1 C23 1.332(10) . ?
F2 C23 1.347(11) . ?
F3 C23 1.324(9) . ?
N1 C2 1.311(9) . ?
N1 C3 1.350(10) . ?
C1 C5 1.370(10) . ?
C1 C2 1.427(10) . ?
C2 C23 1.502(13) . ?
C3 C15 1.408(11) . ?
C3 C4 1.426(10) . ?
C4 C12 1.420(11) . ?
C4 C5 1.432(10) . ?
C5 C6 1.493(9) . ?
C6 C11 1.367(10) . ?
C6 C7 1.392(10) . ?
C7 C8 1.395(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(11) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.357(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.423(14) . ?
C13 C16 1.492(12) . ?
C14 C15 1.349(13) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.376(11) . ?
C17 C18 1.388(10) . ?
C18 C19 1.368(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(13) . ?
C21 H21 0.9300 . ?
C22 H22 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
C17 Se1 C1 98.1(3) . . ?
C2 N1 C3 118.0(7) . . ?
C5 C1 C2 118.7(7) . . ?
C5 C1 Se1 122.0(5) . . ?
C2 C1 Se1 119.3(6) . . ?
N1 C2 C1 124.1(9) . . ?
N1 C2 C23 112.7(7) . . ?
C1 C2 C23 123.2(6) . . ?
N1 C3 C15 118.5(7) . . ?
N1 C3 C4 123.1(6) . . ?
C15 C3 C4 118.3(8) . . ?
C12 C4 C3 118.5(7) . . ?
C12 C4 C5 124.2(7) . . ?
C3 C4 C5 117.3(6) . . ?
C1 C5 C4 118.8(6) . . ?
C1 C5 C6 122.6(6) . . ?
C4 C5 C6 118.6(6) . . ?
C11 C6 C7 118.6(7) . . ?
C11 C6 C5 121.7(6) . . ?
C7 C6 C5 119.7(6) . . ?
C6 C7 C8 121.0(8) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 119.2(7) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.5(7) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 118.8(8) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C6 C11 C10 121.8(7) . . ?
C6 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C13 C12 C4 122.1(7) . . ?
C13 C12 H12 118.9 . . ?
C4 C12 H12 118.9 . . ?
C12 C13 C14 118.3(8) . . ?
C12 C13 C16 122.1(8) . . ?
C14 C13 C16 119.6(8) . . ?
C15 C14 C13 121.5(8) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C3 121.2(8) . . ?
C14 C15 H15 119.4 . . ?
C3 C15 H15 119.4 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 119.9(7) . . ?
C22 C17 Se1 120.5(6) . . ?
C18 C17 Se1 119.6(6) . . ?
C19 C18 C17 119.6(8) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 121.0(8) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.1(8) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C22 C21 C20 120.1(8) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C17 C22 C21 120.2(8) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
F3 C23 F1 105.8(8) . . ?
F3 C23 F2 106.2(8) . . ?
F1 C23 F2 104.4(7) . . ?
F3 C23 C2 113.8(7) . . ?
F1 C23 C2 113.2(7) . . ?
F2 C23 C2 112.7(8) . . ?

_refine_diff_density_max         0.975
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.064

