# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 2150878'
loop_
_audit_author_name
_audit_author_address
zhongwei.hou
;Taizhou University
China
;
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 Cl F O4 Se'
_chemical_formula_weight         441.73

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'
Cl Cl 0.1484 0.1585 '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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.4845(8)
_cell_length_b                   10.2563(12)
_cell_length_c                   13.5628(15)
_cell_angle_alpha                99.603(2)
_cell_angle_beta                 100.338(2)
_cell_angle_gamma                109.552(2)
_cell_volume                     935.81(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2599
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      26.42

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    2.179
_shelx_estimated_absorpt_T_min   0.601
_shelx_estimated_absorpt_T_max   0.658
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4789
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.980
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3270
_reflns_number_gt                2786
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.2951P] 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_number_reflns         3270
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.68961(5) 0.34194(3) 0.10310(2) 0.05479(13) Uani 1 1 d . . . . .
Cl1 Cl 1.10868(15) -0.16067(11) 0.09748(7) 0.0788(3) Uani 1 1 d . . . . .
F1 F 0.8189(2) 0.14432(18) 0.38564(12) 0.0559(4) Uani 1 1 d . . . . .
O4 O 0.3604(3) 0.1417(2) 0.40575(17) 0.0552(5) Uani 1 1 d . . . . .
O2 O 0.6832(3) 0.4191(2) 0.48824(16) 0.0616(6) Uani 1 1 d . . . . .
O3 O 0.4770(4) -0.0316(2) 0.3820(2) 0.0745(7) Uani 1 1 d . . . . .
C4 C 0.8158(4) 0.1450(3) 0.18319(18) 0.0363(5) Uani 1 1 d . . . . .
C15 C 0.6825(4) 0.2070(3) 0.38763(19) 0.0391(6) Uani 1 1 d . . . . .
O1 O 0.8904(4) 0.3278(3) 0.55704(19) 0.0852(8) Uani 1 1 d . . . . .
C8 C 0.5860(4) 0.4760(3) 0.1617(2) 0.0448(6) Uani 1 1 d . . . . .
C14 C 0.6524(4) 0.2667(3) 0.29455(19) 0.0379(6) Uani 1 1 d . . . . .
H14 H 0.5805 0.3251 0.2957 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7178(4) 0.2445(3) 0.2111(2) 0.0376(5) Uani 1 1 d . . . . .
C18 C 0.4939(4) 0.0896(3) 0.39087(19) 0.0414(6) Uani 1 1 d . . . . .
C1 C 0.9942(4) -0.0423(3) 0.1282(2) 0.0483(7) Uani 1 1 d . . . . .
C3 C 0.7125(4) -0.0009(3) 0.1565(2) 0.0504(7) Uani 1 1 d . . . . .
H3 H 0.5810 -0.0364 0.1570 0.060 Uiso 1 1 calc R U . . .
C16 C 0.7649(4) 0.3246(3) 0.4889(2) 0.0447(6) Uani 1 1 d . . . . .
C5 C 1.0105(4) 0.1949(3) 0.1787(2) 0.0446(6) Uani 1 1 d . . . . .
H5 H 1.0812 0.2927 0.1940 0.054 Uiso 1 1 calc R U . . .
C6 C 1.1004(4) 0.1020(3) 0.1520(2) 0.0507(7) Uani 1 1 d . . . . .
H6 H 1.2312 0.1364 0.1502 0.061 Uiso 1 1 calc R U . . .
C2 C 0.8016(5) -0.0946(3) 0.1291(2) 0.0544(7) Uani 1 1 d . . . . .
H2 H 0.7308 -0.1925 0.1114 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4004(4) 0.4636(3) 0.1133(2) 0.0497(7) Uani 1 1 d . . . . .
H13 H 0.3268 0.3892 0.0554 0.060 Uiso 1 1 calc R U . . .
C9 C 0.6949(5) 0.5856(3) 0.2475(3) 0.0650(9) Uani 1 1 d . . . . .
H9 H 0.8209 0.5959 0.2803 0.078 Uiso 1 1 calc R U . . .
C12 C 0.3236(5) 0.5611(4) 0.1505(3) 0.0638(9) Uani 1 1 d . . . . .
H12 H 0.1992 0.5529 0.1168 0.077 Uiso 1 1 calc R U . . .
C19 C 0.1745(4) 0.0403(4) 0.4114(3) 0.0686(10) Uani 1 1 d . . . . .
H19A H 0.1188 -0.0343 0.3489 0.103 Uiso 1 1 calc R U . . .
H19B H 0.0862 0.0885 0.4198 0.103 Uiso 1 1 calc R U . . .
H19C H 0.1960 -0.0002 0.4693 0.103 Uiso 1 1 calc R U . . .
C11 C 0.4270(6) 0.6672(4) 0.2347(3) 0.0730(10) Uani 1 1 d . . . . .
H11 H 0.3734 0.7317 0.2597 0.088 Uiso 1 1 calc R U . . .
C17 C 0.7517(5) 0.5374(4) 0.5795(3) 0.0721(10) Uani 1 1 d . . . . .
H17A H 0.7132 0.6131 0.5627 0.108 Uiso 1 1 calc R U . . .
H17B H 0.8919 0.5717 0.6025 0.108 Uiso 1 1 calc R U . . .
H17C H 0.6950 0.5055 0.6335 0.108 Uiso 1 1 calc R U . . .
C10 C 0.6116(7) 0.6812(3) 0.2843(3) 0.0809(12) Uani 1 1 d . . . . .
H10 H 0.6819 0.7550 0.3430 0.097 Uiso 1 1 calc R U . . .


_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 C8 1.922(3) . ?
Se1 C7 1.925(2) . ?
Cl1 C1 1.743(3) . ?
F1 C15 1.378(3) . ?
O4 C18 1.311(3) . ?
O4 C19 1.456(3) . ?
O2 C16 1.308(3) . ?
O2 C17 1.457(4) . ?
O3 C18 1.189(3) . ?
C4 C3 1.383(4) . ?
C4 C5 1.390(4) . ?
C4 C7 1.481(3) . ?
C15 C14 1.506(3) . ?
C15 C18 1.532(4) . ?
C15 C16 1.538(4) . ?
O1 C16 1.181(3) . ?
C8 C9 1.376(4) . ?
C8 C13 1.379(4) . ?
C14 C7 1.327(3) . ?
C14 H14 0.9300 . ?
C1 C2 1.362(4) . ?
C1 C6 1.374(4) . ?
C3 C2 1.381(4) . ?
C3 H3 0.9300 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C13 C12 1.381(4) . ?
C13 H13 0.9300 . ?
C9 C10 1.399(5) . ?
C9 H9 0.9300 . ?
C12 C11 1.339(5) . ?
C12 H12 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C11 C10 1.372(6) . ?
C11 H11 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C10 H10 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
C8 Se1 C7 101.86(11) . . ?
C18 O4 C19 116.2(2) . . ?
C16 O2 C17 117.2(2) . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 C7 120.5(2) . . ?
C5 C4 C7 121.3(2) . . ?
F1 C15 C14 111.17(19) . . ?
F1 C15 C18 105.9(2) . . ?
C14 C15 C18 111.7(2) . . ?
F1 C15 C16 105.3(2) . . ?
C14 C15 C16 111.8(2) . . ?
C18 C15 C16 110.7(2) . . ?
C9 C8 C13 120.0(3) . . ?
C9 C8 Se1 121.6(2) . . ?
C13 C8 Se1 118.4(2) . . ?
C7 C14 C15 126.7(2) . . ?
C7 C14 H14 116.6 . . ?
C15 C14 H14 116.6 . . ?
C14 C7 C4 128.3(2) . . ?
C14 C7 Se1 122.36(19) . . ?
C4 C7 Se1 109.35(17) . . ?
O3 C18 O4 126.1(3) . . ?
O3 C18 C15 122.8(2) . . ?
O4 C18 C15 111.1(2) . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 Cl1 119.4(2) . . ?
C6 C1 Cl1 119.3(2) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O1 C16 O2 125.4(3) . . ?
O1 C16 C15 122.4(3) . . ?
O2 C16 C15 112.2(2) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C8 C13 C12 120.2(3) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C8 C9 C10 118.4(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C15 C14 C7 10.9(4) . . . . ?
C18 C15 C14 C7 -107.1(3) . . . . ?
C16 C15 C14 C7 128.2(3) . . . . ?
C15 C14 C7 C4 7.4(4) . . . . ?
C15 C14 C7 Se1 -174.0(2) . . . . ?
C3 C4 C7 C14 69.2(4) . . . . ?
C5 C4 C7 C14 -113.6(3) . . . . ?
C3 C4 C7 Se1 -109.5(2) . . . . ?
C5 C4 C7 Se1 67.7(3) . . . . ?
C19 O4 C18 O3 -0.2(4) . . . . ?
C19 O4 C18 C15 -179.4(2) . . . . ?
F1 C15 C18 O3 -6.9(3) . . . . ?
C14 C15 C18 O3 114.2(3) . . . . ?
C16 C15 C18 O3 -120.5(3) . . . . ?
F1 C15 C18 O4 172.2(2) . . . . ?
C14 C15 C18 O4 -66.6(3) . . . . ?
C16 C15 C18 O4 58.6(3) . . . . ?
C5 C4 C3 C2 1.9(4) . . . . ?
C7 C4 C3 C2 179.2(3) . . . . ?
C17 O2 C16 O1 -0.5(4) . . . . ?
C17 O2 C16 C15 -179.0(2) . . . . ?
F1 C15 C16 O1 -16.9(4) . . . . ?
C14 C15 C16 O1 -137.8(3) . . . . ?
C18 C15 C16 O1 97.0(3) . . . . ?
F1 C15 C16 O2 161.6(2) . . . . ?
C14 C15 C16 O2 40.8(3) . . . . ?
C18 C15 C16 O2 -84.4(3) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C7 C4 C5 C6 -179.5(2) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
Cl1 C1 C6 C5 -178.4(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
Cl1 C1 C2 C3 178.1(2) . . . . ?
C4 C3 C2 C1 -0.1(5) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
Se1 C8 C13 C12 -177.5(2) . . . . ?
C13 C8 C9 C10 0.8(4) . . . . ?
Se1 C8 C9 C10 178.4(2) . . . . ?
C8 C13 C12 C11 -1.0(5) . . . . ?
C13 C12 C11 C10 0.8(5) . . . . ?
C12 C11 C10 C9 0.3(5) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.052

