# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 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_cd1_a
_database_code_depnum_ccdc_archive 'CCDC 2213816'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N O Se'
_chemical_formula_sum            'C19 H17 N O Se'
_chemical_formula_weight         354.29

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'

_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                   30.890(2)
_cell_length_b                   5.5621(3)
_cell_length_c                   18.6660(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.111(2)
_cell_angle_gamma                90
_cell_volume                     3188.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7012
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.46

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.356
_shelx_estimated_absorpt_T_min   0.590
_shelx_estimated_absorpt_T_max   0.782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_T_max  0.764
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22589
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         26.830
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3387
_reflns_number_gt                2821
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0216P)²+3.7026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3387
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0530
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.43985(2) 0.10303(4) 0.71301(2) 0.02745(7) Uani 1 1 d . . . . .
O1 O 0.47657(4) 0.2003(3) 0.45959(8) 0.0340(3) Uani 1 1 d . . . . .
N1 N 0.43466(5) -0.0694(3) 0.54364(8) 0.0238(3) Uani 1 1 d . . . . .
H1N H 0.459811 -0.034760 0.524044 0.029 Uiso 1 1 d R U . . .
C1 C 0.37985(6) 0.0138(4) 0.71647(10) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.34733(7) 0.1632(4) 0.68415(11) 0.0310(4) Uani 1 1 d . . . . .
H2A H 0.354776 0.305164 0.659979 0.037 Uiso 1 1 calc R U . . .
C3 C 0.30385(7) 0.1036(5) 0.68737(12) 0.0380(5) Uani 1 1 d . . . . .
H3A H 0.281619 0.205989 0.665503 0.046 Uiso 1 1 calc R U . . .
C4 C 0.29277(7) -0.1022(4) 0.72198(12) 0.0377(5) Uani 1 1 d . . . . .
H4A H 0.262994 -0.142538 0.723442 0.045 Uiso 1 1 calc R U . . .
C5 C 0.32508(7) -0.2507(4) 0.75472(12) 0.0349(5) Uani 1 1 d . . . . .
H5A H 0.317447 -0.392586 0.778787 0.042 Uiso 1 1 calc R U . . .
C6 C 0.36866(6) -0.1921(4) 0.75233(11) 0.0292(4) Uani 1 1 d . . . . .
H6A H 0.390785 -0.292896 0.775257 0.035 Uiso 1 1 calc R U . . .
C7 C 0.45960(6) -0.1900(4) 0.66862(10) 0.0252(4) Uani 1 1 d . . . . .
H7A H 0.490526 -0.169741 0.660381 0.030 Uiso 1 1 calc R U . . .
H7B H 0.457970 -0.325160 0.702753 0.030 Uiso 1 1 calc R U . . .
C8 C 0.43354(6) -0.2559(4) 0.59738(10) 0.0250(4) Uani 1 1 d . . . . .
H8A H 0.445396 -0.406308 0.578873 0.030 Uiso 1 1 calc R U . . .
H8B H 0.402920 -0.286353 0.605832 0.030 Uiso 1 1 calc R U . . .
C9 C 0.40163(6) 0.0706(4) 0.52258(9) 0.0234(4) Uani 1 1 d . . . . .
H9A H 0.374927 0.038576 0.541724 0.028 Uiso 1 1 calc R U . . .
C10 C 0.40214(6) 0.2633(4) 0.47441(9) 0.0229(4) Uani 1 1 d . . . . .
C11 C 0.44246(6) 0.3247(4) 0.44614(10) 0.0254(4) Uani 1 1 d . . . . .
C12 C 0.44299(6) 0.5395(4) 0.40267(10) 0.0286(4) Uani 1 1 d . . . . .
H12A H 0.469215 0.584392 0.383862 0.034 Uiso 1 1 calc R U . . .
C13 C 0.40728(6) 0.6783(4) 0.38802(10) 0.0295(4) Uani 1 1 d . . . . .
H13A H 0.409185 0.819530 0.359901 0.035 Uiso 1 1 calc R U . . .
C14 C 0.36644(6) 0.6178(4) 0.41390(10) 0.0261(4) Uani 1 1 d . . . . .
C15 C 0.32981(7) 0.7665(4) 0.39712(11) 0.0322(5) Uani 1 1 d . . . . .
H15A H 0.332314 0.906557 0.368717 0.039 Uiso 1 1 calc R U . . .
C16 C 0.29048(7) 0.7113(4) 0.42135(12) 0.0374(5) Uani 1 1 d . . . . .
H16A H 0.265962 0.812816 0.410051 0.045 Uiso 1 1 calc R U . . .
C17 C 0.28699(7) 0.5052(4) 0.46261(12) 0.0375(5) Uani 1 1 d . . . . .
H17A H 0.259784 0.465740 0.478996 0.045 Uiso 1 1 calc R U . . .
C18 C 0.32235(6) 0.3573(4) 0.48009(11) 0.0318(5) Uani 1 1 d . . . . .
H18A H 0.319109 0.217725 0.508349 0.038 Uiso 1 1 calc R U . . .
C19 C 0.36341(6) 0.4101(4) 0.45665(9) 0.0242(4) Uani 1 1 d . . . . .


_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 1.9263(19) . ?
Se1 C7 1.955(2) . ?
O1 C11 1.263(2) . ?
N1 C9 1.311(2) . ?
N1 C8 1.446(2) . ?
N1 H1N 0.9139 . ?
C1 C6 1.389(3) . ?
C1 C2 1.391(3) . ?
C2 C3 1.391(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.524(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.400(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.444(2) . ?
C10 C19 1.457(3) . ?
C11 C12 1.445(3) . ?
C12 C13 1.350(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.438(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.410(3) . ?
C14 C19 1.413(3) . ?
C15 C16 1.375(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.378(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.416(3) . ?
C18 H18A 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 C7 98.29(8) . . ?
C9 N1 C8 124.01(15) . . ?
C9 N1 H1N 115.0 . . ?
C8 N1 H1N 120.9 . . ?
C6 C1 C2 119.75(18) . . ?
C6 C1 Se1 121.23(15) . . ?
C2 C1 Se1 118.98(16) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 119.97(19) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 120.04(19) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C8 C7 Se1 114.23(13) . . ?
C8 C7 H7A 108.7 . . ?
Se1 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
Se1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C7 112.55(16) . . ?
N1 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 C10 125.88(16) . . ?
N1 C9 H9A 117.1 . . ?
C10 C9 H9A 117.1 . . ?
C9 C10 C11 118.99(17) . . ?
C9 C10 C19 120.64(16) . . ?
C11 C10 C19 120.25(17) . . ?
O1 C11 C10 122.10(18) . . ?
O1 C11 C12 120.37(17) . . ?
C10 C11 C12 117.52(17) . . ?
C13 C12 C11 121.91(18) . . ?
C13 C12 H12A 119.0 . . ?
C11 C12 H12A 119.0 . . ?
C12 C13 C14 121.68(19) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C15 C14 C19 120.36(18) . . ?
C15 C14 C13 120.02(19) . . ?
C19 C14 C13 119.62(18) . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 H16A 120.4 . . ?
C17 C16 H16A 120.4 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18A 119.4 . . ?
C19 C18 H18A 119.4 . . ?
C14 C19 C18 117.34(17) . . ?
C14 C19 C10 118.97(16) . . ?
C18 C19 C10 123.69(19) . . ?

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 -0.7(3) . . . . ?
Se1 C1 C2 C3 -178.76(15) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
Se1 C1 C6 C5 179.23(15) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C9 N1 C8 C7 -107.2(2) . . . . ?
Se1 C7 C8 N1 59.31(18) . . . . ?
C8 N1 C9 C10 175.47(17) . . . . ?
N1 C9 C10 C11 -2.4(3) . . . . ?
N1 C9 C10 C19 -178.37(18) . . . . ?
C9 C10 C11 O1 4.9(3) . . . . ?
C19 C10 C11 O1 -179.11(18) . . . . ?
C9 C10 C11 C12 -173.61(17) . . . . ?
C19 C10 C11 C12 2.4(3) . . . . ?
O1 C11 C12 C13 -179.14(19) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C15 -179.62(19) . . . . ?
C12 C13 C14 C19 0.9(3) . . . . ?
C19 C14 C15 C16 -0.6(3) . . . . ?
C13 C14 C15 C16 179.94(19) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C15 C14 C19 C18 1.2(3) . . . . ?
C13 C14 C19 C18 -179.35(17) . . . . ?
C15 C14 C19 C10 -178.58(17) . . . . ?
C13 C14 C19 C10 0.9(3) . . . . ?
C17 C18 C19 C14 -0.9(3) . . . . ?
C17 C18 C19 C10 178.87(19) . . . . ?
C9 C10 C19 C14 173.38(17) . . . . ?
C11 C10 C19 C14 -2.5(3) . . . . ?
C9 C10 C19 C18 -6.4(3) . . . . ?
C11 C10 C19 C18 177.73(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.91 1.89 2.612(2) 134.8 . yes
N1 H1N O1 0.91 2.16 2.844(2) 130.7 5_656 yes

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.053

