# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
# 
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data_YCSD18_p383_0m
_database_code_depnum_ccdc_archive 'CCDC 2311150'
loop_
_audit_author_name
_audit_author_address
'William H Hersh'
;Queens College, City University of New York
United States of America
;
_audit_update_record             
;
2023-11-29 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
;
 3-(4-chlorophenyl)-2-((4-fluorophenyl)selanyl)benzo[4,5]
  imidazo[2,1-b]thiazole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 Cl F N2 S Se'
_chemical_formula_sum            'C21 H12 Cl F N2 S Se'
_chemical_formula_weight         457.80

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'
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'
Cl Cl 0.1484 0.1585 '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                   9.2475(173)
_cell_length_b                   9.9092(187)
_cell_length_c                   11.8955(222)
_cell_angle_alpha                70.528(22)
_cell_angle_beta                 67.961(21)
_cell_angle_gamma                73.477(23)
_cell_volume                     937(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2601
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      22.97

_exptl_crystal_description       fragment
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   0.6532
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.178
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_special_details           
;
 A crystal obtained by slow diffusion of pet ether into a dichloromethane
 solution of 5h at room temperature over two days was cleaved in two 
 directions from a large plate and mounted on a 200 micron MiTeGen 
 MicroMount in Paratone-N oil at room temperature.
 A total of 1464 frames were collected and the total exposure time was 5.69 hr.
;
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus tube'
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            10528
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.910
_diffrn_reflns_theta_max         27.206
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4102
_reflns_number_gt                2580
_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 Instrument Service v2018.1.0.3'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  'Mercury 2020.1 (Build 280191)'
_refine_special_details          
;
 Hydrogen atom positions were calculated and isotropic thermal
 parameters were fixed for all C-H hydrogen atoms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4102
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_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 0.10130(3) 0.59015(3) 0.68894(3) 0.06439(12) Uani 1 1 d . . . . .
Cl1 Cl 0.71718(10) 0.24588(9) 0.95445(8) 0.0908(3) Uani 1 1 d . . . . .
S1 S 0.21038(7) 0.86929(7) 0.47786(6) 0.05768(19) Uani 1 1 d . . . . .
F1 F -0.3451(2) 0.91566(19) 1.06796(15) 0.0914(5) Uani 1 1 d . . . . .
N1 N 0.4895(2) 0.78806(19) 0.49766(16) 0.0420(4) Uani 1 1 d . . . . .
N2 N 0.4829(2) 0.9914(2) 0.33824(17) 0.0522(5) Uani 1 1 d . . . . .
C1 C -0.0349(3) 0.7028(2) 0.8056(2) 0.0486(6) Uani 1 1 d . . . . .
C2 C -0.1754(3) 0.7888(3) 0.7885(2) 0.0543(6) Uani 1 1 d . . . . .
H1 H -0.199420 0.798225 0.716750 0.065 Uiso 1 1 calc R U . . .
C3 C -0.2797(3) 0.8605(3) 0.8766(3) 0.0606(7) Uani 1 1 d . . . . .
H2 H -0.374628 0.918018 0.865486 0.073 Uiso 1 1 calc R U . . .
C4 C -0.2419(3) 0.8459(3) 0.9802(3) 0.0606(7) Uani 1 1 d . . . . .
C5 C -0.1049(3) 0.7634(3) 1.0003(2) 0.0690(8) Uani 1 1 d . . . . .
H4 H -0.082033 0.756083 1.072077 0.083 Uiso 1 1 calc R U . . .
C6 C 0.0001(3) 0.6905(3) 0.9121(2) 0.0625(7) Uani 1 1 d . . . . .
H3 H 0.094458 0.633108 0.924408 0.075 Uiso 1 1 calc R U . . .
C7 C 0.2547(3) 0.7098(3) 0.5904(2) 0.0503(6) Uani 1 1 d . . . . .
C8 C 0.4026(3) 0.8982(3) 0.4288(2) 0.0468(6) Uani 1 1 d . . . . .
C9 C 0.4064(3) 0.6834(2) 0.5909(2) 0.0450(5) Uani 1 1 d . . . . .
C10 C 0.4819(3) 0.5724(2) 0.6802(2) 0.0443(5) Uani 1 1 d . . . . .
C11 C 0.5423(3) 0.6177(3) 0.7497(2) 0.0525(6) Uani 1 1 d . . . . .
H8 H 0.534344 0.716625 0.738893 0.063 Uiso 1 1 calc R U . . .
C12 C 0.6134(3) 0.5181(3) 0.8337(2) 0.0586(7) Uani 1 1 d . . . . .
H7 H 0.652765 0.549229 0.880372 0.070 Uiso 1 1 calc R U . . .
C13 C 0.6262(3) 0.3728(3) 0.8488(2) 0.0564(6) Uani 1 1 d . . . . .
C14 C 0.5673(3) 0.3250(3) 0.7814(2) 0.0604(7) Uani 1 1 d . . . . .
H5 H 0.576549 0.225874 0.792123 0.073 Uiso 1 1 calc R U . . .
C15 C 0.4948(3) 0.4248(3) 0.6983(2) 0.0547(6) Uani 1 1 d . . . . .
H6 H 0.453668 0.392830 0.653430 0.066 Uiso 1 1 calc R U . . .
C16 C 0.6462(3) 0.8105(2) 0.4406(2) 0.0438(5) Uani 1 1 d . . . . .
C17 C 0.6374(3) 0.9384(3) 0.3438(2) 0.0480(6) Uani 1 1 d . . . . .
C18 C 0.7745(3) 0.9909(3) 0.2671(2) 0.0615(7) Uani 1 1 d . . . . .
H9 H 0.770826 1.076411 0.203664 0.074 Uiso 1 1 calc R U . . .
C19 C 0.9158(3) 0.9157(3) 0.2856(2) 0.0679(8) Uani 1 1 d . . . . .
H12 H 1.008761 0.950502 0.234413 0.081 Uiso 1 1 calc R U . . .
C20 C 0.9223(3) 0.7869(3) 0.3805(3) 0.0637(7) Uani 1 1 d . . . . .
H10 H 1.020320 0.736537 0.389830 0.076 Uiso 1 1 calc R U . . .
C21 C 0.7877(3) 0.7326(3) 0.4605(2) 0.0530(6) Uani 1 1 d . . . . .
H11 H 0.792039 0.647804 0.524506 0.064 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 C7 1.891(3) . ?
Se1 C1 1.918(3) . ?
Cl1 C13 1.734(3) . ?
S1 C8 1.727(4) . ?
S1 C7 1.758(3) . ?
F1 C4 1.356(3) . ?
N1 C8 1.382(3) . ?
N1 C9 1.395(3) . ?
N1 C16 1.398(4) . ?
N2 C8 1.300(3) . ?
N2 C17 1.394(4) . ?
C1 C6 1.381(4) . ?
C1 C2 1.381(4) . ?
C2 C3 1.371(4) . ?
C2 H1 0.9300 . ?
C3 C4 1.355(4) . ?
C3 H2 0.9300 . ?
C4 C5 1.356(4) . ?
C5 C6 1.381(4) . ?
C5 H4 0.9300 . ?
C6 H3 0.9300 . ?
C7 C9 1.353(4) . ?
C9 C10 1.472(3) . ?
C10 C15 1.382(4) . ?
C10 C11 1.390(3) . ?
C11 C12 1.368(3) . ?
C11 H8 0.9300 . ?
C12 C13 1.367(4) . ?
C12 H7 0.9300 . ?
C13 C14 1.376(4) . ?
C14 C15 1.367(4) . ?
C14 H5 0.9300 . ?
C15 H6 0.9300 . ?
C16 C21 1.378(4) . ?
C16 C17 1.406(4) . ?
C17 C18 1.379(4) . ?
C18 C19 1.365(4) . ?
C18 H9 0.9300 . ?
C19 C20 1.397(4) . ?
C19 H12 0.9300 . ?
C20 C21 1.377(4) . ?
C20 H10 0.9300 . ?
C21 H11 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
C7 Se1 C1 100.48(16) . . ?
C8 S1 C7 90.62(13) . . ?
C8 N1 C9 115.7(2) . . ?
C8 N1 C16 105.5(2) . . ?
C9 N1 C16 138.41(19) . . ?
C8 N2 C17 103.4(2) . . ?
C6 C1 C2 119.2(2) . . ?
C6 C1 Se1 120.5(2) . . ?
C2 C1 Se1 120.1(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H1 119.7 . . ?
C1 C2 H1 119.7 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H2 120.6 . . ?
C2 C3 H2 120.6 . . ?
C3 C4 F1 119.0(3) . . ?
C3 C4 C5 122.7(3) . . ?
F1 C4 C5 118.3(3) . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 H4 120.6 . . ?
C6 C5 H4 120.6 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H3 120.0 . . ?
C1 C6 H3 120.0 . . ?
C9 C7 S1 112.80(18) . . ?
C9 C7 Se1 126.7(2) . . ?
S1 C7 Se1 120.39(16) . . ?
N2 C8 N1 115.2(2) . . ?
N2 C8 S1 134.63(19) . . ?
N1 C8 S1 109.9(2) . . ?
C7 C9 N1 110.9(2) . . ?
C7 C9 C10 128.8(2) . . ?
N1 C9 C10 120.0(2) . . ?
C15 C10 C11 118.5(2) . . ?
C15 C10 C9 122.8(2) . . ?
C11 C10 C9 118.7(2) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H8 119.7 . . ?
C10 C11 H8 119.7 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H7 120.2 . . ?
C11 C12 H7 120.2 . . ?
C12 C13 C14 120.9(2) . . ?
C12 C13 Cl1 120.0(2) . . ?
C14 C13 Cl1 119.2(2) . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H5 120.3 . . ?
C13 C14 H5 120.3 . . ?
C14 C15 C10 121.0(2) . . ?
C14 C15 H6 119.5 . . ?
C10 C15 H6 119.5 . . ?
C21 C16 N1 133.1(2) . . ?
C21 C16 C17 122.6(2) . . ?
N1 C16 C17 104.3(2) . . ?
C18 C17 N2 129.2(2) . . ?
C18 C17 C16 119.2(2) . . ?
N2 C17 C16 111.6(2) . . ?
C19 C18 C17 119.1(3) . . ?
C19 C18 H9 120.5 . . ?
C17 C18 H9 120.5 . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 H12 119.6 . . ?
C20 C19 H12 119.6 . . ?
C21 C20 C19 121.9(3) . . ?
C21 C20 H10 119.1 . . ?
C19 C20 H10 119.1 . . ?
C20 C21 C16 116.5(3) . . ?
C20 C21 H11 121.8 . . ?
C16 C21 H11 121.8 . . ?

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
C6 C1 C2 C3 -0.5(4) . . . . ?
Se1 C1 C2 C3 174.67(19) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 F1 -179.6(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
F1 C4 C5 C6 179.2(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
Se1 C1 C6 C5 -175.0(2) . . . . ?
C8 S1 C7 C9 1.16(18) . . . . ?
C8 S1 C7 Se1 -175.64(14) . . . . ?
C1 Se1 C7 C9 107.6(2) . . . . ?
C1 Se1 C7 S1 -76.04(19) . . . . ?
C17 N2 C8 N1 1.6(2) . . . . ?
C17 N2 C8 S1 -171.9(2) . . . . ?
C9 N1 C8 N2 -176.89(18) . . . . ?
C16 N1 C8 N2 -2.7(2) . . . . ?
C9 N1 C8 S1 -1.8(2) . . . . ?
C16 N1 C8 S1 172.43(14) . . . . ?
C7 S1 C8 N2 174.1(2) . . . . ?
C7 S1 C8 N1 0.34(16) . . . . ?
S1 C7 C9 N1 -2.3(2) . . . . ?
Se1 C7 C9 N1 174.25(15) . . . . ?
S1 C7 C9 C10 171.84(18) . . . . ?
Se1 C7 C9 C10 -11.6(4) . . . . ?
C8 N1 C9 C7 2.7(3) . . . . ?
C16 N1 C9 C7 -168.9(2) . . . . ?
C8 N1 C9 C10 -172.07(18) . . . . ?
C16 N1 C9 C10 16.4(4) . . . . ?
C7 C9 C10 C15 61.6(3) . . . . ?
N1 C9 C10 C15 -124.8(2) . . . . ?
C7 C9 C10 C11 -118.1(3) . . . . ?
N1 C9 C10 C11 55.5(3) . . . . ?
C15 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 C12 180.0(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C11 C12 C13 Cl1 179.61(19) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
Cl1 C13 C14 C15 179.73(19) . . . . ?
C13 C14 C15 C10 0.8(4) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C9 C10 C15 C14 179.4(2) . . . . ?
C8 N1 C16 C21 -175.0(2) . . . . ?
C9 N1 C16 C21 -2.9(4) . . . . ?
C8 N1 C16 C17 2.4(2) . . . . ?
C9 N1 C16 C17 174.5(2) . . . . ?
C8 N2 C17 C18 177.6(2) . . . . ?
C8 N2 C17 C16 0.0(2) . . . . ?
C21 C16 C17 C18 -1.7(3) . . . . ?
N1 C16 C17 C18 -179.42(19) . . . . ?
C21 C16 C17 N2 176.1(2) . . . . ?
N1 C16 C17 N2 -1.6(2) . . . . ?
N2 C17 C18 C19 -176.1(2) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
C19 C20 C21 C16 1.2(4) . . . . ?
N1 C16 C21 C20 177.4(2) . . . . ?
C17 C16 C21 C20 0.4(3) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.050





