# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_compound_3q
_database_code_depnum_ccdc_archive 'CCDC 2169580'
loop_
_audit_author_name
_audit_author_address
'Roberta Cargnelutti'
;Federal University of Santa Maria
Brazil
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H16 O2 Se'
_chemical_formula_sum            'C25 H16 O2 Se'
_chemical_formula_weight         427.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.835(3)
_cell_length_b                   16.655(3)
_cell_length_c                   8.5970(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.296(7)
_cell_angle_gamma                90
_cell_volume                     1891.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.76

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    2.003
_shelx_estimated_absorpt_T_min   0.555
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
SADABS (Bruker 2014 - version 2014/5) was used to perform the multi-scan
absorption correction.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(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            70153
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.968
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5798
_reflns_number_gt                4227
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  Diamond
_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)+(0.0288P)²+0.8998P] 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         5798
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.002
_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 0.71752(2) 0.59561(2) 0.61004(2) 0.04535(7) Uani 1 1 d . . . . .
C1 C 0.78609(13) 0.61795(11) 0.8344(2) 0.0405(4) Uani 1 1 d . . . . .
O1 O 0.61636(10) 0.36107(7) 0.58349(15) 0.0429(3) Uani 1 1 d . . . . .
O2 O 0.54841(11) 0.57056(8) 0.77213(19) 0.0562(4) Uani 1 1 d . . . . .
C2 C 0.80534(13) 0.69754(11) 0.8786(2) 0.0423(4) Uani 1 1 d . . . . .
H2 H 0.780905 0.737823 0.802077 0.051 Uiso 1 1 calc R U . . .
C4 C 0.89506(18) 0.65894(15) 1.1503(3) 0.0630(6) Uani 1 1 d . . . . .
H4 H 0.932542 0.672568 1.255931 0.076 Uiso 1 1 calc R U . . .
C3 C 0.86056(15) 0.71748(13) 1.0355(2) 0.0517(5) Uani 1 1 d . . . . .
H3 H 0.874467 0.771096 1.063483 0.062 Uiso 1 1 calc R U . . .
C5 C 0.8740(2) 0.58040(15) 1.1086(3) 0.0749(7) Uani 1 1 d . . . . .
H5 H 0.895745 0.540668 1.187234 0.090 Uiso 1 1 calc R U . . .
C6 C 0.82053(19) 0.55899(13) 0.9501(3) 0.0629(6) Uani 1 1 d . . . . .
H6 H 0.808074 0.505201 0.922280 0.076 Uiso 1 1 calc R U . . .
C7 C 0.64967(13) 0.49967(10) 0.6394(2) 0.0393(4) Uani 1 1 d . . . . .
C8 C 0.57112(14) 0.50668(11) 0.7213(2) 0.0416(4) Uani 1 1 d . . . . .
C9 C 0.52202(13) 0.43041(11) 0.7383(2) 0.0390(4) Uani 1 1 d . . . . .
C10 C 0.54737(13) 0.36086(10) 0.6704(2) 0.0384(4) Uani 1 1 d . . . . .
C11 C 0.66758(13) 0.42965(10) 0.5736(2) 0.0391(4) Uani 1 1 d . . . . .
C12 C 0.45158(15) 0.42449(12) 0.8252(2) 0.0476(4) Uani 1 1 d . . . . .
H12 H 0.431943 0.470397 0.869451 0.057 Uiso 1 1 calc R U . . .
C13 C 0.41099(16) 0.35124(13) 0.8457(2) 0.0534(5) Uani 1 1 d . . . . .
H13 H 0.364444 0.347831 0.904333 0.064 Uiso 1 1 calc R U . . .
C14 C 0.43936(15) 0.28229(12) 0.7791(2) 0.0504(5) Uani 1 1 d . . . . .
H14 H 0.412480 0.232847 0.794875 0.060 Uiso 1 1 calc R U . . .
C15 C 0.50678(14) 0.28679(11) 0.6902(2) 0.0446(4) Uani 1 1 d . . . . .
H15 H 0.524949 0.240903 0.643939 0.054 Uiso 1 1 calc R U . . .
C16 C 0.73917(13) 0.41438(10) 0.4780(2) 0.0399(4) Uani 1 1 d . . . . .
C17 C 0.70154(14) 0.38540(11) 0.3231(2) 0.0413(4) Uani 1 1 d . . . . .
H17 H 0.632174 0.377389 0.279737 0.050 Uiso 1 1 calc R U . . .
C18 C 0.76599(14) 0.36734(10) 0.2272(2) 0.0417(4) Uani 1 1 d . . . . .
C19 C 0.87167(14) 0.37925(12) 0.2953(3) 0.0485(4) Uani 1 1 d . . . . .
C20 C 0.90808(15) 0.40919(13) 0.4552(3) 0.0577(5) Uani 1 1 d . . . . .
H20 H 0.977255 0.417440 0.500487 0.069 Uiso 1 1 calc R U . . .
C21 C 0.84463(15) 0.42643(13) 0.5454(3) 0.0535(5) Uani 1 1 d . . . . .
H21 H 0.870609 0.446049 0.650943 0.064 Uiso 1 1 calc R U . . .
C22 C 0.72817(17) 0.33710(13) 0.0668(3) 0.0542(5) Uani 1 1 d . . . . .
H22 H 0.658904 0.329180 0.021868 0.065 Uiso 1 1 calc R U . . .
C23 C 0.7916(2) 0.31941(14) -0.0230(3) 0.0660(6) Uani 1 1 d . . . . .
H23 H 0.765767 0.299338 -0.128130 0.079 Uiso 1 1 calc R U . . .
C24 C 0.8956(2) 0.33149(16) 0.0434(3) 0.0742(7) Uani 1 1 d . . . . .
H24 H 0.938554 0.319174 -0.018325 0.089 Uiso 1 1 calc R U . . .
C25 C 0.93521(18) 0.36094(15) 0.1968(3) 0.0668(6) Uani 1 1 d . . . . .
H25 H 1.004651 0.369225 0.237737 0.080 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 1.9076(17) . ?
Se1 C1 1.9161(18) . ?
C1 C6 1.378(3) . ?
C1 C2 1.383(2) . ?
O1 C11 1.360(2) . ?
O1 C10 1.376(2) . ?
O2 C8 1.226(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C4 C5 1.365(3) . ?
C4 C3 1.369(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.351(2) . ?
C7 C8 1.465(3) . ?
C8 C9 1.468(2) . ?
C9 C10 1.388(2) . ?
C9 C12 1.396(3) . ?
C10 C15 1.387(2) . ?
C11 C16 1.485(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.366(2) . ?
C16 C21 1.415(3) . ?
C17 C18 1.415(2) . ?
C17 H17 0.9300 . ?
C18 C22 1.414(3) . ?
C18 C19 1.418(3) . ?
C19 C20 1.407(3) . ?
C19 C25 1.424(3) . ?
C20 C21 1.364(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.362(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.395(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.360(4) . ?
C24 H24 0.9300 . ?
C25 H25 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 98.35(7) . . ?
C6 C1 C2 119.21(18) . . ?
C6 C1 Se1 123.34(15) . . ?
C2 C1 Se1 117.38(14) . . ?
C11 O1 C10 119.62(13) . . ?
C3 C2 C1 120.33(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C3 C2 120.47(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C11 C7 C8 121.66(16) . . ?
C11 C7 Se1 120.60(13) . . ?
C8 C7 Se1 117.48(12) . . ?
O2 C8 C7 123.09(17) . . ?
O2 C8 C9 122.70(17) . . ?
C7 C8 C9 114.21(15) . . ?
C10 C9 C12 118.01(17) . . ?
C10 C9 C8 119.87(16) . . ?
C12 C9 C8 122.10(17) . . ?
O1 C10 C15 116.12(16) . . ?
O1 C10 C9 121.94(15) . . ?
C15 C10 C9 121.92(17) . . ?
C7 C11 O1 122.36(16) . . ?
C7 C11 C16 127.96(16) . . ?
O1 C11 C16 109.64(14) . . ?
C13 C12 C9 120.50(19) . . ?
C13 C12 H12 119.8 . . ?
C9 C12 H12 119.8 . . ?
C12 C13 C14 120.21(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.39(18) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 118.94(18) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
C17 C16 C21 119.80(17) . . ?
C17 C16 C11 118.47(16) . . ?
C21 C16 C11 121.69(16) . . ?
C16 C17 C18 121.31(17) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C22 C18 C17 121.95(17) . . ?
C22 C18 C19 119.31(18) . . ?
C17 C18 C19 118.74(17) . . ?
C20 C19 C18 118.61(18) . . ?
C20 C19 C25 123.5(2) . . ?
C18 C19 C25 117.9(2) . . ?
C21 C20 C19 121.75(18) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C16 119.80(19) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
C23 C22 C18 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C18 C22 H22 119.5 . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 121.2(2) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C19 120.8(2) . . ?
C24 C25 H25 119.6 . . ?
C19 C25 H25 119.6 . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.054

