# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_ZEP1064_3
_database_code_depnum_ccdc_archive 'CCDC 2121570'
loop_
_audit_author_name
_audit_author_address
'Uwe Monkowius'
;Johannes Kepler University Linz, Linz School of Education
Austria
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H21 N O4 Se'
_chemical_formula_sum            'C20 H21 N O4 Se'
_chemical_formula_iupac          ?
_chemical_formula_weight         418.34

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.198(5)
_cell_length_b                   10.355(7)
_cell_length_c                   12.174(7)
_cell_angle_alpha                69.365(16)
_cell_angle_beta                 76.44(2)
_cell_angle_gamma                64.56(2)
_cell_volume                     975.2(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9727
_cell_measurement_theta_min      2.4562
_cell_measurement_theta_max      25.0033
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       bloc
_exptl_crystal_colour            'clear colourless-yellow'
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428

_exptl_absorpt_coefficient_mu    1.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.64

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   sealed
_diffrn_source_type              ?
_diffrn_source_power             1.00
_diffrn_source_current           20.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       'Bruker D8 Quest ECO'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'φ and ω scans'


_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            60514
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3429
_reflns_number_gt                3176
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0745
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_restrained_S_all      1.215
_refine_ls_number_reflns         3429
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.2986P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.390
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se1 0.18963(2) 0.39070(2) 0.31388(2) 0.04797(10) Uani d . . . 1 . .
O O3 0.54205(18) 0.13540(19) 0.14804(13) 0.0529(4) Uani d . . . 1 . .
O O1 0.28330(19) 0.09121(19) 0.21331(14) 0.0536(4) Uani d . . . 1 . .
O O4 0.5860(2) 0.0960(2) 0.33426(15) 0.0680(5) Uani d . . . 1 . .
O O2 0.0300(2) 0.2398(2) 0.18117(15) 0.0647(5) Uani d . . . 1 . .
N N1 0.3876(2) 0.0458(2) 0.30164(16) 0.0504(4) Uani d . . . 1 . .
C C4 -0.0185(2) 0.2276(2) 0.44396(19) 0.0431(5) Uani d . . . 1 . .
C C2 0.1334(2) 0.2077(2) 0.36130(17) 0.0401(4) Uani d . . . 1 . .
C C10 -0.0107(3) 0.5405(2) 0.26011(18) 0.0440(5) Uani d . . . 1 . .
C C16 0.5127(3) 0.0991(3) 0.2639(2) 0.0501(5) Uani d . . . 1 . .
C C6 -0.1431(4) 0.2106(4) 0.6429(2) 0.0724(8) Uani d . . . 1 . .
H H6 -0.133108 0.1815 0.723194 0.087 Uiso calc U . R 1 . .
C C1 0.1334(3) 0.1872(3) 0.24497(19) 0.0459(5) Uani d . . . 1 . .
C C7 -0.2925(3) 0.2777(3) 0.6042(3) 0.0729(8) Uani d . . . 1 . .
H H7 -0.384513 0.296508 0.657449 0.087 Uiso calc U . R 1 . .
C C11 -0.1300(3) 0.6037(3) 0.3402(2) 0.0500(5) Uani d . . . 1 . .
H H11 -0.110951 0.573806 0.418753 0.06 Uiso calc U . R 1 . .
C C5 -0.0060(3) 0.1853(3) 0.5641(2) 0.0582(6) Uani d . . . 1 . .
H H5 0.095558 0.139465 0.591734 0.07 Uiso calc U . R 1 . .
C C12 -0.2769(3) 0.7107(3) 0.3040(2) 0.0602(6) Uani d . . . 1 . .
H H12 -0.356658 0.753386 0.357908 0.072 Uiso calc U . R 1 . .
C C3 0.2828(3) 0.0749(3) 0.40819(19) 0.0504(5) Uani d . . . 1 . .
H H3A 0.33437 0.098499 0.455373 0.061 Uiso calc U . R 1 . .
H H3B 0.255902 -0.010654 0.455752 0.061 Uiso calc U . R 1 . .
C C8 -0.3066(3) 0.3173(3) 0.4861(3) 0.0695(7) Uani d . . . 1 . .
H H8 -0.408745 0.36114 0.459622 0.083 Uiso calc U . R 1 . .
C C9 -0.1704(3) 0.2929(3) 0.4060(2) 0.0557(6) Uani d . . . 1 . .
H H9 -0.181576 0.320658 0.326012 0.067 Uiso calc U . R 1 . .
C C13 -0.3053(3) 0.7538(3) 0.1890(3) 0.0681(7) Uani d . . . 1 . .
H H13 -0.40498 0.825204 0.164846 0.082 Uiso calc U . R 1 . .
C C15 -0.0392(3) 0.5863(3) 0.1432(2) 0.0584(6) Uani d . . . 1 . .
H H15 0.040822 0.545769 0.088381 0.07 Uiso calc U . R 1 . .
C C17 0.6753(3) 0.1893(3) 0.0896(2) 0.0587(6) Uani d . . . 1 . .
C C18 0.6406(4) 0.3309(3) 0.1177(3) 0.0713(7) Uani d . . . 1 . .
H H18A 0.531433 0.398369 0.103113 0.107 Uiso calc U . R 1 . .
H H18B 0.714029 0.376507 0.068717 0.107 Uiso calc U . R 1 . .
H H18C 0.65426 0.307949 0.199099 0.107 Uiso calc U . R 1 . .
C C14 -0.1873(4) 0.6924(3) 0.1087(2) 0.0729(8) Uani d . . . 1 . .
H H14 -0.207594 0.722784 0.030334 0.087 Uiso calc U . R 1 . .
C C19 0.8354(3) 0.0680(4) 0.1278(3) 0.0810(9) Uani d . . . 1 . .
H H19A 0.839005 0.050938 0.210065 0.122 Uiso calc U . R 1 . .
H H19B 0.921954 0.098409 0.082721 0.122 Uiso calc U . R 1 . .
H H19C 0.847112 -0.022282 0.114757 0.122 Uiso calc U . R 1 . .
C C20 0.6607(5) 0.2192(5) -0.0391(3) 0.0968(12) Uani d . . . 1 . .
H H20A 0.679594 0.127714 -0.053621 0.145 Uiso calc U . R 1 . .
H H20B 0.739183 0.258967 -0.0873 0.145 Uiso calc U . R 1 . .
H H20C 0.554005 0.289933 -0.057949 0.145 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Se1 C10 . 1.903(2) ?
Se1 C2 . 2.030(2) ?
O3 C16 . 1.318(3) ?
O3 C17 . 1.490(3) ?
O1 C1 . 1.371(3) ?
O1 N1 . 1.428(3) ?
O4 C16 . 1.193(3) ?
O2 C1 . 1.186(3) ?
N1 C16 . 1.399(3) ?
N1 C3 . 1.464(3) ?
C4 C9 . 1.377(3) ?
C4 C5 . 1.389(3) ?
C4 C2 . 1.499(3) ?
C2 C1 . 1.505(3) ?
C2 C3 . 1.516(3) ?
C10 C15 . 1.383(3) ?
C10 C11 . 1.384(3) ?
C6 C7 . 1.359(4) ?
C6 C5 . 1.380(4) ?
C7 C8 . 1.370(4) ?
C11 C12 . 1.377(3) ?
C12 C13 . 1.363(4) ?
C8 C9 . 1.384(4) ?
C13 C14 . 1.373(4) ?
C15 C14 . 1.377(4) ?
C17 C18 . 1.505(4) ?
C17 C19 . 1.511(4) ?
C17 C20 . 1.513(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 Se1 C2 . . 99.31(10) ?
C16 O3 C17 . . 120.07(18) ?
C1 O1 N1 . . 108.95(16) ?
C16 N1 O1 . . 114.16(17) ?
C16 N1 C3 . . 118.0(2) ?
O1 N1 C3 . . 106.54(17) ?
C9 C4 C5 . . 118.4(2) ?
C9 C4 C2 . . 123.0(2) ?
C5 C4 C2 . . 118.5(2) ?
C4 C2 C1 . . 117.92(18) ?
C4 C2 C3 . . 115.85(17) ?
C1 C2 C3 . . 101.47(17) ?
C4 C2 Se1 . . 110.48(14) ?
C1 C2 Se1 . . 103.39(13) ?
C3 C2 Se1 . . 106.38(15) ?
C15 C10 C11 . . 119.6(2) ?
C15 C10 Se1 . . 121.34(17) ?
C11 C10 Se1 . . 119.06(17) ?
O4 C16 O3 . . 128.2(2) ?
O4 C16 N1 . . 120.1(2) ?
O3 C16 N1 . . 111.3(2) ?
C7 C6 C5 . . 120.5(3) ?
O2 C1 O1 . . 119.1(2) ?
O2 C1 C2 . . 131.1(2) ?
O1 C1 C2 . . 109.80(18) ?
C6 C7 C8 . . 119.6(2) ?
C12 C11 C10 . . 120.2(2) ?
C6 C5 C4 . . 120.6(3) ?
C13 C12 C11 . . 119.9(2) ?
N1 C3 C2 . . 103.84(17) ?
C7 C8 C9 . . 120.6(3) ?
C4 C9 C8 . . 120.3(3) ?
C12 C13 C14 . . 120.3(3) ?
C14 C15 C10 . . 119.4(2) ?
O3 C17 C18 . . 109.0(2) ?
O3 C17 C19 . . 109.7(2) ?
C18 C17 C19 . . 112.8(2) ?
O3 C17 C20 . . 101.2(2) ?
C18 C17 C20 . . 111.4(3) ?
C19 C17 C20 . . 112.0(3) ?
C13 C14 C15 . . 120.5(2) ?




_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
