# 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_4C
_database_code_depnum_ccdc_archive 'CCDC 2213814'
loop_
_audit_author_name
_audit_author_address
'Atash Gurbanov'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;

# start Validation Reply Form                                                                                                             
_vrf_PLAT430_4C                  
;                                                                                                                                         
PROBLEM:  Short Inter D...A Contact Se1 ..O5 . 2.69 Ang. x,1+y,z = 1_565 Check
          Short Inter D...A Contact Se2 ..O6 . 2.77 Ang. x,1+y,z = 1_565 Check                                                                                                                                                      
RESPONSE: The A Alert draw attention to the possibility of missed hydrogen bonds as indicated by short Donor - Acceptor atom distances.   
In the structures of the present work placing H atoms on the marked atoms is not reasonable at all and the warnings are just              
indicative of the Non-Covalent Interactions between the involved atoms.
;
# end Validation Reply Form 


_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H N3 O2 Se, C3 H7 N O'
_chemical_formula_sum            'C7 H8 N4 O3 Se'
_chemical_formula_weight         275.13

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   21.779(3)
_cell_length_b                   3.8696(4)
_cell_length_c                   24.330(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2050.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9800
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.48

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.656
_shelx_estimated_absorpt_T_min   0.428
_shelx_estimated_absorpt_T_max   0.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.515
_exptl_absorpt_correction_T_max  0.612
_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            34443
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.870
_diffrn_reflns_theta_max         26.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4207
_reflns_number_gt                3975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.996

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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          
;
 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)+(0.0063P)²+12.3170P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.22(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4207
_refine_ls_number_parameters     282
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.111
_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 0.52641(3) 0.4320(2) 0.52107(3) 0.01735(18) Uani 1 1 d . . . . .
Se2 Se 0.19783(3) 0.4460(2) 0.47825(3) 0.01708(18) Uani 1 1 d . . . . .
O1 O 0.4421(3) -0.2302(19) 0.3688(3) 0.0288(16) Uani 1 1 d . . . . .
O2 O 0.3659(3) -0.018(2) 0.4226(3) 0.0351(18) Uani 1 1 d D . . . .
H2O H 0.332(3) -0.11(2) 0.408(5) 0.053 Uiso 1 1 d D U . . .
O3 O 0.2813(3) -0.2310(18) 0.6298(3) 0.0239(14) Uani 1 1 d . . . . .
O4 O 0.3578(3) -0.011(2) 0.5759(3) 0.036(2) Uani 1 1 d D . . . .
H4O H 0.385(4) -0.14(3) 0.595(4) 0.055 Uiso 1 1 d D U . . .
N1 N 0.5715(3) 0.309(2) 0.4619(3) 0.0164(15) Uani 1 1 d . . . . .
N2 N 0.4566(3) 0.2622(19) 0.4904(3) 0.0158(15) Uani 1 1 d . . . . .
N3 N 0.5878(4) -0.082(3) 0.3399(3) 0.0299(19) Uani 1 1 d . . . . .
N4 N 0.1528(3) 0.332(2) 0.5383(3) 0.0181(15) Uani 1 1 d . . . . .
N5 N 0.2676(3) 0.2717(19) 0.5083(3) 0.0178(16) Uani 1 1 d . . . . .
N6 N 0.1365(4) -0.031(2) 0.6625(3) 0.0287(18) Uani 1 1 d . . . . .
C1 C 0.5349(4) 0.154(2) 0.4272(3) 0.0155(17) Uani 1 1 d . . . . .
C2 C 0.4707(4) 0.133(2) 0.4429(3) 0.0158(17) Uani 1 1 d . . . . .
C3 C 0.5619(4) 0.021(2) 0.3766(3) 0.0183(18) Uani 1 1 d . . . . .
C4 C 0.4245(4) -0.054(2) 0.4079(4) 0.0169(17) Uani 1 1 d . . . . .
C5 C 0.1893(4) 0.176(3) 0.5729(3) 0.0161(17) Uani 1 1 d . . . . .
C6 C 0.2529(4) 0.141(2) 0.5572(3) 0.0143(16) Uani 1 1 d . . . . .
C7 C 0.1628(4) 0.053(3) 0.6238(4) 0.0224(19) Uani 1 1 d . . . . .
C8 C 0.2997(4) -0.047(2) 0.5913(3) 0.0197(17) Uani 1 1 d . . . . .
O5 O 0.4603(3) -0.421(2) 0.6113(3) 0.0311(16) Uani 1 1 d D . . . .
N7 N 0.4754(3) -0.415(2) 0.7036(3) 0.0244(17) Uani 1 1 d . . . . .
C9 C 0.4927(4) -0.474(3) 0.6517(4) 0.025(2) Uani 1 1 d . . . . .
H9 H 0.532761 -0.563401 0.645727 0.030 Uiso 1 1 calc R U . . .
C10 C 0.4136(4) -0.285(3) 0.7151(4) 0.028(2) Uani 1 1 d . . . . .
H10A H 0.413221 -0.032932 0.711692 0.042 Uiso 1 1 calc R U . . .
H10B H 0.401629 -0.350772 0.752476 0.042 Uiso 1 1 calc R U . . .
H10C H 0.384561 -0.385332 0.688735 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5181(4) -0.467(3) 0.7493(4) 0.034(2) Uani 1 1 d . . . . .
H11A H 0.555096 -0.583753 0.735867 0.052 Uiso 1 1 calc R U . . .
H11B H 0.498444 -0.609858 0.777552 0.052 Uiso 1 1 calc R U . . .
H11C H 0.529296 -0.242809 0.765068 0.052 Uiso 1 1 calc R U . . .
O6 O 0.2648(3) -0.435(2) 0.3836(3) 0.0307(16) Uani 1 1 d D . . . .
N8 N 0.2645(3) -0.649(2) 0.2962(3) 0.0208(16) Uani 1 1 d . . . . .
C12 C 0.2381(4) -0.567(3) 0.3440(4) 0.026(2) Uani 1 1 d . . . . .
H12A H 0.195483 -0.614127 0.347924 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2284(4) -0.801(3) 0.2510(4) 0.027(2) Uani 1 1 d . . . . .
H13A H 0.226788 -0.638263 0.220208 0.040 Uiso 1 1 calc R U . . .
H13B H 0.186650 -0.849459 0.263881 0.040 Uiso 1 1 calc R U . . .
H13C H 0.247828 -1.016570 0.238957 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3292(4) -0.592(3) 0.2868(4) 0.028(2) Uani 1 1 d . . . . .
H14A H 0.347705 -0.488793 0.319590 0.042 Uiso 1 1 calc R U . . .
H14B H 0.334519 -0.435732 0.255434 0.042 Uiso 1 1 calc R U . . .
H14C H 0.349258 -0.813252 0.278827 0.042 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 N1 1.807(7) . ?
Se1 N2 1.817(7) . ?
Se2 N4 1.815(7) . ?
Se2 N5 1.816(7) . ?
O1 C4 1.230(11) . ?
O2 C4 1.333(11) . ?
O2 H2O 0.88(2) . ?
O3 C8 1.242(11) . ?
O4 C8 1.326(11) . ?
O4 H4O 0.88(3) . ?
N1 C1 1.306(11) . ?
N2 C2 1.297(11) . ?
N3 C3 1.129(11) . ?
N4 C5 1.304(11) . ?
N5 C6 1.332(10) . ?
N6 C7 1.149(12) . ?
C1 C2 1.451(12) . ?
C1 C3 1.459(11) . ?
C2 C4 1.505(12) . ?
C5 C6 1.444(11) . ?
C5 C7 1.448(12) . ?
C6 C8 1.501(12) . ?
O5 C9 1.227(11) . ?
N7 C9 1.338(11) . ?
N7 C10 1.462(11) . ?
N7 C11 1.464(11) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O6 C12 1.234(11) . ?
N8 C12 1.336(11) . ?
N8 C14 1.444(11) . ?
N8 C13 1.474(10) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
N1 Se1 N2 91.9(3) . . ?
N4 Se2 N5 92.2(3) . . ?
C4 O2 H2O 130(8) . . ?
C8 O4 H4O 115(7) . . ?
C1 N1 Se1 107.6(5) . . ?
C2 N2 Se1 107.9(6) . . ?
C5 N4 Se2 107.6(6) . . ?
C6 N5 Se2 107.5(6) . . ?
N1 C1 C2 116.4(7) . . ?
N1 C1 C3 117.5(7) . . ?
C2 C1 C3 126.1(8) . . ?
N2 C2 C1 116.1(8) . . ?
N2 C2 C4 122.2(8) . . ?
C1 C2 C4 121.6(8) . . ?
N3 C3 C1 173.6(9) . . ?
O1 C4 O2 124.4(8) . . ?
O1 C4 C2 119.7(8) . . ?
O2 C4 C2 115.9(8) . . ?
N4 C5 C6 117.3(7) . . ?
N4 C5 C7 117.5(7) . . ?
C6 C5 C7 125.2(8) . . ?
N5 C6 C5 115.5(7) . . ?
N5 C6 C8 121.0(7) . . ?
C5 C6 C8 123.5(7) . . ?
N6 C7 C5 173.3(10) . . ?
O3 C8 O4 125.5(8) . . ?
O3 C8 C6 118.3(8) . . ?
O4 C8 C6 116.1(8) . . ?
C9 N7 C10 119.9(8) . . ?
C9 N7 C11 120.9(7) . . ?
C10 N7 C11 119.1(7) . . ?
O5 C9 N7 124.5(8) . . ?
O5 C9 H9 117.8 . . ?
N7 C9 H9 117.8 . . ?
N7 C10 H10A 109.5 . . ?
N7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 H11A 109.5 . . ?
N7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N8 C14 121.5(7) . . ?
C12 N8 C13 120.9(7) . . ?
C14 N8 C13 117.5(7) . . ?
O6 C12 N8 125.0(8) . . ?
O6 C12 H12A 117.5 . . ?
N8 C12 H12A 117.5 . . ?
N8 C13 H13A 109.5 . . ?
N8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N8 C14 H14A 109.5 . . ?
N8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
N2 Se1 N1 C1 -1.7(6) . . . . ?
N1 Se1 N2 C2 0.9(6) . . . . ?
N5 Se2 N4 C5 -1.7(7) . . . . ?
N4 Se2 N5 C6 1.6(6) . . . . ?
Se1 N1 C1 C2 2.2(10) . . . . ?
Se1 N1 C1 C3 -178.1(7) . . . . ?
Se1 N2 C2 C1 0.2(9) . . . . ?
Se1 N2 C2 C4 175.4(7) . . . . ?
N1 C1 C2 N2 -1.7(12) . . . . ?
C3 C1 C2 N2 178.6(8) . . . . ?
N1 C1 C2 C4 -176.9(8) . . . . ?
C3 C1 C2 C4 3.4(14) . . . . ?
N2 C2 C4 O1 -165.7(8) . . . . ?
C1 C2 C4 O1 9.3(13) . . . . ?
N2 C2 C4 O2 13.5(13) . . . . ?
C1 C2 C4 O2 -171.6(8) . . . . ?
Se2 N4 C5 C6 1.4(10) . . . . ?
Se2 N4 C5 C7 -178.5(7) . . . . ?
Se2 N5 C6 C5 -1.2(9) . . . . ?
Se2 N5 C6 C8 175.7(6) . . . . ?
N4 C5 C6 N5 -0.2(12) . . . . ?
C7 C5 C6 N5 179.8(9) . . . . ?
N4 C5 C6 C8 -176.9(8) . . . . ?
C7 C5 C6 C8 3.0(15) . . . . ?
N5 C6 C8 O3 -163.6(8) . . . . ?
C5 C6 C8 O3 12.9(14) . . . . ?
N5 C6 C8 O4 13.8(13) . . . . ?
C5 C6 C8 O4 -169.6(9) . . . . ?
C10 N7 C9 O5 1.5(16) . . . . ?
C11 N7 C9 O5 -176.5(11) . . . . ?
C14 N8 C12 O6 1.0(16) . . . . ?
C13 N8 C12 O6 -179.0(10) . . . . ?

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
O4 H4O O5 0.88(3) 2.02(3) 2.870(10) 160(8) . yes
O2 H2O O6 0.88(2) 2.03(3) 2.889(10) 164(10) . yes

_refine_diff_density_max         1.097
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.122



