# Supplementary Information (SI) for Chemical Science.
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2326967'
loop_
_audit_author_name
_audit_author_address
'Mahima Rana'
;IISER Pune
India
;
_audit_update_record             
;
2024-10-09 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2024-10-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 O2 Se'
_chemical_formula_sum            'C15 H12 O2 Se'
_chemical_formula_weight         303.21
_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 0.0033 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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.0359(7)
_cell_length_b                   12.4928(7)
_cell_length_c                   7.6471(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.074(2)
_cell_angle_gamma                90
_cell_volume                     1235.89(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      25.064
_cell_measurement_theta_min      2.267
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.028
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1461 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.7446.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.128
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            34104
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.069
_diffrn_reflns_theta_max         25.069
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2032
_reflns_number_total             2192
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0184
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0164P)²+0.9889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0445
_refine_ls_wR_factor_ref         0.0459
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5), C4(H4), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.37104(2) 0.70362(2) 0.37783(2) 0.01842(7) Uani 1 1 d . . . . .
O1 O 0.39798(9) 0.48634(10) 0.34329(15) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.43753(13) 0.57150(14) 0.3190(2) 0.0133(3) Uani 1 1 d . . . . .
O2 O 0.16950(10) 0.61870(11) 0.15912(16) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.53538(13) 0.58490(14) 0.2398(2) 0.0132(3) Uani 1 1 d . . . . .
C3 C 0.58190(13) 0.49336(14) 0.1809(2) 0.0159(4) Uani 1 1 d . . . . .
H3 H 0.5530 0.4249 0.1979 0.019 Uiso 1 1 calc R U . . .
C6 C 0.66752(14) 0.69304(15) 0.1327(2) 0.0199(4) Uani 1 1 d . . . . .
H6 H 0.6972 0.7613 0.1169 0.024 Uiso 1 1 calc R U . . .
C5 C 0.71265(14) 0.60178(15) 0.0728(2) 0.0202(4) Uani 1 1 d . . . . .
H5 H 0.7728 0.6076 0.0147 0.024 Uiso 1 1 calc R U . . .
C4 C 0.67009(14) 0.50183(15) 0.0977(2) 0.0186(4) Uani 1 1 d . . . . .
H4 H 0.7015 0.4393 0.0576 0.022 Uiso 1 1 calc R U . . .
C7 C 0.57892(13) 0.68490(14) 0.2159(2) 0.0163(4) Uani 1 1 d . . . . .
H7 H 0.5480 0.7475 0.2566 0.020 Uiso 1 1 calc R U . . .
C8 C 0.25171(13) 0.63368(13) 0.4564(2) 0.0128(3) Uani 1 1 d . . . . .
H8A H 0.2758 0.5791 0.5461 0.015 Uiso 1 1 calc R U . . .
H8B H 0.2108 0.6874 0.5132 0.015 Uiso 1 1 calc R U . . .
C9 C 0.18220(13) 0.57987(14) 0.3065(2) 0.0152(4) Uani 1 1 d . . . . .
C10 C 0.12336(13) 0.48289(14) 0.3497(2) 0.0144(4) Uani 1 1 d . . . . .
C11 C 0.16038(13) 0.41186(14) 0.4835(2) 0.0156(4) Uani 1 1 d . . . . .
H11 H 0.2249 0.4252 0.5523 0.019 Uiso 1 1 calc R U . . .
C12 C 0.10354(14) 0.32207(14) 0.5165(2) 0.0187(4) Uani 1 1 d . . . . .
H12 H 0.1293 0.2739 0.6075 0.022 Uiso 1 1 calc R U . . .
C13 C 0.00907(14) 0.30229(15) 0.4171(3) 0.0215(4) Uani 1 1 d . . . . .
H13 H -0.0296 0.2405 0.4397 0.026 Uiso 1 1 calc R U . . .
C14 C -0.02882(14) 0.37300(16) 0.2847(2) 0.0232(4) Uani 1 1 d . . . . .
H14 H -0.0938 0.3598 0.2173 0.028 Uiso 1 1 calc R U . . .
C15 C 0.02783(13) 0.46260(15) 0.2505(2) 0.0191(4) Uani 1 1 d . . . . .
H15 H 0.0018 0.5105 0.1592 0.023 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 C1 1.9427(17) . ?
Se1 C8 1.9429(16) . ?
O1 C1 1.206(2) . ?
C1 C2 1.487(2) . ?
O2 C9 1.220(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.393(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(3) . ?
C6 C7 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.527(2) . ?
C9 C10 1.492(2) . ?
C10 C11 1.395(2) . ?
C10 C15 1.399(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9500 . ?

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 C8 94.96(7) . . ?
O1 C1 Se1 120.15(13) . . ?
O1 C1 C2 124.47(15) . . ?
C2 C1 Se1 115.35(12) . . ?
C3 C2 C1 117.90(15) . . ?
C7 C2 C1 122.53(15) . . ?
C7 C2 C3 119.50(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.28(17) . . ?
C4 C3 H3 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.11(17) . . ?
C7 C6 H6 119.9 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.09(17) . . ?
C4 C5 H5 120.0 . . ?
C3 C4 C5 119.97(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.04(17) . . ?
C6 C7 H7 120.0 . . ?
Se1 C8 H8A 109.0 . . ?
Se1 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 Se1 112.92(11) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
O2 C9 C8 121.29(16) . . ?
O2 C9 C10 120.82(16) . . ?
C10 C9 C8 117.71(14) . . ?
C11 C10 C9 122.54(15) . . ?
C11 C10 C15 119.14(17) . . ?
C15 C10 C9 118.32(16) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.31(16) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.21(17) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.90(17) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.16(17) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.28(17) . . ?
C14 C15 H15 119.9 . . ?

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
Se1 C1 C2 C3 -174.58(12) . . . . ?
Se1 C1 C2 C7 2.6(2) . . . . ?
Se1 C8 C9 O2 -35.0(2) . . . . ?
Se1 C8 C9 C10 149.87(12) . . . . ?
O1 C1 C2 C3 3.6(2) . . . . ?
O1 C1 C2 C7 -179.28(16) . . . . ?
C1 C2 C3 C4 176.57(15) . . . . ?
C1 C2 C7 C6 -176.58(15) . . . . ?
O2 C9 C10 C11 154.01(16) . . . . ?
O2 C9 C10 C15 -25.5(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C2 C7 C6 0.5(2) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
C7 C6 C5 C4 -0.8(3) . . . . ?
C8 C9 C10 C11 -30.9(2) . . . . ?
C8 C9 C10 C15 149.65(15) . . . . ?
C9 C10 C11 C12 -178.98(15) . . . . ?
C9 C10 C15 C14 179.30(15) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
C15 C10 C11 C12 0.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
