# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# 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. 
# 
#######################################################################

data_4d
_database_code_depnum_ccdc_archive 'CCDC 2309404'
loop_
_audit_author_name
_audit_author_address
'Patrizia Rossi'
;University of Firenze
Italy
;
_audit_update_record             
;
2024-01-10 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_4d                  
;
PROBLEM: Short Inter D...A Contact Se1 ..O1 . 2.85 Ang.
RESPONSE: ...
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 N O2 Se'
_chemical_formula_weight         268.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   12.9756(11)
_cell_length_b                   7.1286(6)
_cell_length_c                   22.9309(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2121.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      5.15
_cell_measurement_theta_max      68.55


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    4.631
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5525
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2016/2, Sheldrick 2015'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            16898
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         5.148
_diffrn_reflns_theta_max         68.585
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1920
_reflns_number_gt                1835
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+26.9848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1914
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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 0.17992(4) 0.60445(9) 0.27589(2) 0.0188(2) Uani 1 1 d . . . . .
O1 O 0.4862(3) 0.5954(6) 0.28288(16) 0.0241(9) Uani 1 1 d . . . . .
O2 O 0.2283(3) 0.6586(6) 0.39131(17) 0.0250(9) Uani 1 1 d . . . . .
N1 N 0.3137(3) 0.6106(6) 0.3080(2) 0.0160(9) Uani 1 1 d . . . . .
C1 C 0.2484(4) 0.5800(8) 0.2033(2) 0.0206(12) Uani 1 1 d . . . . .
C2 C 0.2013(4) 0.5638(8) 0.1493(3) 0.0225(12) Uani 1 1 d . . . . .
H2 H 0.132(6) 0.571(9) 0.147(3) 0.027 Uiso 1 1 d . U . . .
C3 C 0.2635(4) 0.5471(9) 0.1004(2) 0.0250(13) Uani 1 1 d . . . . .
H3 H 0.232(5) 0.538(10) 0.063(3) 0.030 Uiso 1 1 d . U . . .
C4 C 0.3705(5) 0.5455(9) 0.1054(3) 0.0242(13) Uani 1 1 d . . . . .
H4 H 0.413(5) 0.535(10) 0.072(3) 0.029 Uiso 1 1 d . U . . .
C5 C 0.4166(4) 0.5607(9) 0.1595(3) 0.0224(12) Uani 1 1 d . . . . .
H5 H 0.486(5) 0.561(9) 0.163(3) 0.027 Uiso 1 1 d . U . . .
C6 C 0.3547(4) 0.5778(8) 0.2090(2) 0.0193(12) Uani 1 1 d . . . . .
C7 C 0.3952(4) 0.5964(8) 0.2688(2) 0.0197(11) Uani 1 1 d . . . . .
C8 C 0.3124(4) 0.6465(8) 0.3681(2) 0.0202(12) Uani 1 1 d . . . . .
C9 C 0.4128(4) 0.6643(9) 0.4012(3) 0.0224(12) Uani 1 1 d . . . . .
H9 H 0.464(5) 0.722(10) 0.376(3) 0.027 Uiso 1 1 d . U . . .
C10 C 0.3965(5) 0.7819(10) 0.4560(3) 0.0280(14) Uani 1 1 d . . . . .
H10A H 0.465(6) 0.798(11) 0.478(3) 0.042 Uiso 1 1 d . U . . .
H10B H 0.350(6) 0.726(11) 0.484(3) 0.042 Uiso 1 1 d . U . . .
H10C H 0.375(6) 0.917(12) 0.446(3) 0.042 Uiso 1 1 d . U . . .
C11 C 0.4504(5) 0.4658(10) 0.4165(3) 0.0257(13) Uani 1 1 d . . . . .
H11A H 0.463(6) 0.396(11) 0.381(3) 0.039 Uiso 1 1 d . U . . .
H11B H 0.513(6) 0.471(11) 0.437(3) 0.039 Uiso 1 1 d . U . . .
H11C H 0.397(6) 0.381(11) 0.441(3) 0.039 Uiso 1 1 d . 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 1.886(4) . ?
Se1 C1 1.894(5) . ?
O1 C7 1.224(7) . ?
O2 C8 1.217(7) . ?
N1 C7 1.391(7) . ?
N1 C8 1.403(7) . ?
C1 C2 1.387(8) . ?
C1 C6 1.385(8) . ?
C2 C3 1.387(8) . ?
C3 C4 1.394(8) . ?
C4 C5 1.381(8) . ?
C5 C6 1.396(8) . ?
C6 C7 1.476(8) . ?
C8 C9 1.512(8) . ?
C9 C10 1.525(8) . ?
C9 C11 1.537(9) . ?

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 C1 85.0(2) . . ?
C7 N1 C8 131.1(4) . . ?
C7 N1 Se1 116.5(4) . . ?
C8 N1 Se1 112.1(3) . . ?
C2 C1 C6 121.4(5) . . ?
C2 C1 Se1 125.8(4) . . ?
C6 C1 Se1 112.7(4) . . ?
C1 C2 C3 118.2(5) . . ?
C2 C3 C4 120.9(5) . . ?
C5 C4 C3 120.3(5) . . ?
C4 C5 C6 119.2(5) . . ?
C1 C6 C5 119.9(5) . . ?
C1 C6 C7 116.1(5) . . ?
C5 C6 C7 124.0(5) . . ?
O1 C7 N1 124.3(5) . . ?
O1 C7 C6 126.0(5) . . ?
N1 C7 C6 109.7(4) . . ?
O2 C8 N1 116.9(5) . . ?
O2 C8 C9 123.2(5) . . ?
N1 C8 C9 119.9(5) . . ?
C8 C9 C10 109.9(5) . . ?
C8 C9 C11 108.1(5) . . ?
C10 C9 C11 111.2(5) . . ?

_refine_diff_density_max         0.791
_refine_diff_density_min         -1.325
_refine_diff_density_rms         0.123

