# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# 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. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2332095'
loop_
_audit_author_name
_audit_author_address
'Amey P. Wadawale'
;Bhabha Atomic Research Centre
India
;
_audit_update_record             
;
2024-02-09 deposited with the CCDC.	2024-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H4 D16 O8 Se4'
_chemical_formula_weight         624.22

# start Validation Reply Form
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Resid. Dens.  2.25Ang From Se1             2.77 eA-3  
RESPONSE: Probably due to unresolvable twinning arising to from 
the crystals which were sgglomerates of smaller crystallites 
with extensive twinning 
;
# end Validation Reply Form

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   5.5158(6)
_cell_length_b                   9.1291(9)
_cell_length_c                   19.1868(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.815(9)
_cell_angle_gamma                90
_cell_volume                     962.73(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1449
_cell_measurement_theta_min      4.2570
_cell_measurement_theta_max      26.9630

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.153
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    7.655
_shelx_estimated_absorpt_T_min   0.515
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_T_min  0.5148
_exptl_absorpt_correction_T_max  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.621
_oxdiff_exptl_absorpt_empirical_full_max 1.875
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      298(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            3830
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.264
_diffrn_reflns_theta_max         30.655
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_orient_matrix_UB_11      -0.0147322000
_diffrn_orient_matrix_UB_12      -0.0183323000
_diffrn_orient_matrix_UB_13      -0.0360237000
_diffrn_orient_matrix_UB_21      -0.1047105000
_diffrn_orient_matrix_UB_22      0.0453003000
_diffrn_orient_matrix_UB_23      -0.0042591000
_diffrn_orient_matrix_UB_31      0.0739700000
_diffrn_orient_matrix_UB_32      0.0604275000
_diffrn_orient_matrix_UB_33      -0.0077350000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  62.00   0.50    2.92    --   -5.10  51.00   4.00   80
  2  ω    -20.00  27.00   0.50    2.92    --   -5.10 -99.00 -60.00   94
  3  ω    -18.00  28.00   0.50    2.92    --   -5.10 -99.00  90.00   92
  4  ω    -20.00  20.00   0.50    2.92    --   -5.10 -99.00 150.00   80
  5  ω    -60.00   8.00   0.50    2.92    --   -5.10 -51.00-141.00  136
;
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_digest_frames     
;
01e9936e76964e95a88a52869c7534ee7c004827361
;
_diffrn_oxdiff_digest_hkl        
;
01c908d84697d7c2a6ce5e742a8737f3d94e8f
;
_reflns_number_total             1202
_reflns_number_gt                849
_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_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.1284P)²+15.5350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1202
_refine_ls_number_parameters     69
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0917
_refine_ls_wR_factor_ref         0.2572
_refine_ls_wR_factor_gt          0.2470
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_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 0.3455(2) 0.61989(14) 0.70558(6) 0.0498(5) Uani 1 1 d . . . . .
C2 C 0.6888(18) 0.4798(11) 0.6203(5) 0.035(2) Uani 1 1 d D . . . .
C1 C 0.444(2) 0.4609(11) 0.6459(5) 0.038(2) Uani 1 1 d D . . . .
O2 O 0.9351(14) 0.6309(9) 0.5572(5) 0.0501(19) Uani 1 1 d . . . . .
H2 H 0.936973 0.706708 0.534249 0.075 Uiso 1 1 calc R U . . .
O1 O 0.5342(14) 0.6642(9) 0.5390(4) 0.0492(19) Uani 1 1 d . . . . .
C3 C 0.7082(19) 0.5984(10) 0.5686(5) 0.033(2) Uani 1 1 d . . . . .
D2A D 0.834(9) 0.480(12) 0.653(3) 0.040 Uiso 1 1 d D U . . .
D2B D 0.71(2) 0.390(7) 0.594(5) 0.040 Uiso 1 1 d D U . . .
D1A D 0.420(14) 0.404(10) 0.687(3) 0.040 Uiso 1 1 d D U . . .
D1B D 0.304(13) 0.458(12) 0.612(4) 0.040 Uiso 1 1 d D 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 C1 1.953(11) . ?
Se1 Se1 2.307(2) 2_656 ?
C2 C3 1.478(13) . ?
C2 C1 1.486(15) . ?
C2 D2A 0.97(2) . ?
C2 D2B 0.97(2) . ?
C1 D1A 0.97(2) . ?
C1 D1B 0.97(2) . ?
O2 C3 1.323(12) . ?
O2 H2 0.8200 . ?
O1 C3 1.230(12) . ?

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
C1 Se1 Se1 102.1(3) . 2_656 ?
C3 C2 C1 115.2(8) . . ?
C3 C2 D2A 109(6) . . ?
C1 C2 D2A 120(5) . . ?
C3 C2 D2B 104(7) . . ?
C1 C2 D2B 103(7) . . ?
D2A C2 D2B 103(9) . . ?
C2 C1 Se1 114.4(7) . . ?
C2 C1 D1A 121(5) . . ?
Se1 C1 D1A 82(7) . . ?
C2 C1 D1B 118(7) . . ?
Se1 C1 D1B 100(7) . . ?
D1A C1 D1B 113(8) . . ?
C3 O2 H2 109.5 . . ?
O1 C3 O2 121.7(9) . . ?
O1 C3 C2 124.8(10) . . ?
O2 C3 C2 113.5(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
C3 C2 C1 Se1 -69.6(10) . . . . ?
C1 C2 C3 O1 -11.2(15) . . . . ?
C1 C2 C3 O2 167.7(9) . . . . ?

_refine_diff_density_max         2.745
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.264



