# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_220328_s1_lb
_database_code_depnum_ccdc_archive 'CCDC 2183282'
loop_
_audit_author_name
_audit_author_address
'Bin Li'
;sichuan university
China
;
_audit_update_record             
;
2022-07-01 deposited with the CCDC.	2023-02-21 downloaded from the CCDC.
;
_audit_creation_date             2022-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H15 N O Se'
_chemical_formula_sum            'C16 H15 N O Se'
_chemical_formula_weight         316.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3se1
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.9417(14)
_cell_length_b                   7.4061(8)
_cell_length_c                   12.3726(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.420(11)
_cell_angle_gamma                90
_cell_volume                     1393.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1206
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7740
_cell_measurement_theta_min      3.3170
_shelx_estimated_absorpt_T_max   0.553
_shelx_estimated_absorpt_T_min   0.453
_exptl_absorpt_coefficient_mu    2.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.059
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   57.0000  -30.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega   -6.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   77.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336   38.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega  -73.00  -47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -57.0000   60.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0324046000
_diffrn_orient_matrix_UB_12      0.0046717000
_diffrn_orient_matrix_UB_13      -0.0286579000
_diffrn_orient_matrix_UB_21      0.0335006000
_diffrn_orient_matrix_UB_22      -0.0027659000
_diffrn_orient_matrix_UB_23      0.0526978000
_diffrn_orient_matrix_UB_31      0.0006476000
_diffrn_orient_matrix_UB_32      -0.0956698000
_diffrn_orient_matrix_UB_33      -0.0028641000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1753
_reflns_number_total             2839
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+0.2315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16B,H16A)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.12925(3) 0.82935(6) 0.47724(4) 0.0819(2) Uani 1 1 d . . . . .
O1 O 0.58447(16) 0.8380(4) 0.6304(2) 0.0721(8) Uani 1 1 d . . . . .
N1 N 0.51389(16) 0.8780(3) 0.76525(19) 0.0393(6) Uani 1 1 d . . . . .
C1 C 0.1213(2) 1.0106(5) 0.3644(3) 0.0597(10) Uani 1 1 d . . . . .
C2 C 0.0902(2) 0.9650(7) 0.2518(4) 0.0752(12) Uani 1 1 d . . . . .
H2 H 0.074158 0.846421 0.230729 0.090 Uiso 1 1 calc R . . . .
C3 C 0.0829(3) 1.0953(9) 0.1704(4) 0.0904(15) Uani 1 1 d . . . . .
H3 H 0.062144 1.063832 0.094242 0.108 Uiso 1 1 calc R . . . .
C4 C 0.1056(3) 1.2696(8) 0.1997(4) 0.0895(15) Uani 1 1 d . . . . .
H4 H 0.099456 1.356936 0.143829 0.107 Uiso 1 1 calc R . . . .
C5 C 0.1377(3) 1.3161(6) 0.3121(4) 0.0805(13) Uani 1 1 d . . . . .
H5 H 0.154108 1.434692 0.332575 0.097 Uiso 1 1 calc R . . . .
C6 C 0.1453(3) 1.1871(6) 0.3940(4) 0.0697(11) Uani 1 1 d . . . . .
H6 H 0.166827 1.218753 0.470073 0.084 Uiso 1 1 calc R . . . .
C7 C 0.2494(2) 0.8603(4) 0.5660(3) 0.0507(9) Uani 1 1 d . . . . .
C8 C 0.3145(2) 0.9014(4) 0.5169(3) 0.0475(8) Uani 1 1 d . . . . .
H8 H 0.299444 0.924108 0.439483 0.057 Uiso 1 1 calc R . . . .
C9 C 0.4011(2) 0.9088(4) 0.5815(3) 0.0440(8) Uani 1 1 d . . . . .
H9 H 0.444013 0.937936 0.547448 0.053 Uiso 1 1 calc R . . . .
C10 C 0.4254(2) 0.8735(4) 0.6968(3) 0.0389(7) Uani 1 1 d . . . . .
C11 C 0.3592(2) 0.8353(4) 0.7455(3) 0.0489(9) Uani 1 1 d . . . . .
H11 H 0.373517 0.813327 0.822934 0.059 Uiso 1 1 calc R . . . .
C12 C 0.2728(2) 0.8297(4) 0.6799(3) 0.0556(9) Uani 1 1 d . . . . .
H12 H 0.229293 0.804648 0.713844 0.067 Uiso 1 1 calc R . . . .
C13 C 0.5858(2) 0.8537(4) 0.7284(3) 0.0456(8) Uani 1 1 d . . . . .
C14 C 0.6654(2) 0.8457(4) 0.8296(3) 0.0491(8) Uani 1 1 d . . . . .
H14A H 0.710847 0.925854 0.820172 0.059 Uiso 1 1 calc R . . . .
H14B H 0.688709 0.723802 0.841189 0.059 Uiso 1 1 calc R . . . .
C15 C 0.6351(2) 0.9049(5) 0.9286(3) 0.0559(9) Uani 1 1 d . . . . .
H15A H 0.651283 1.029550 0.948278 0.067 Uiso 1 1 calc R . . . .
H15B H 0.660859 0.829548 0.994284 0.067 Uiso 1 1 calc R . . . .
C16 C 0.5362(2) 0.8837(5) 0.8883(2) 0.0520(9) Uani 1 1 d . . . . .
H16B H 0.518561 0.773040 0.917415 0.062 Uiso 1 1 calc R . . . .
H16A H 0.507790 0.984990 0.912647 0.062 Uiso 1 1 calc R . . . .


_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 1.914(4) . ?
Se1 C7 1.915(3) . ?
O1 C13 1.212(4) . ?
N1 C10 1.412(4) . ?
N1 C13 1.367(4) . ?
N1 C16 1.457(4) . ?
C1 C2 1.373(5) . ?
C1 C6 1.380(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(4) . ?
C7 C12 1.365(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 C11 1.392(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.494(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.510(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.512(4) . ?
C16 H16B 0.9700 . ?
C16 H16A 0.9700 . ?

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 99.84(14) . . ?
C10 N1 C16 121.0(2) . . ?
C13 N1 C10 125.8(3) . . ?
C13 N1 C16 112.7(3) . . ?
C2 C1 Se1 119.5(3) . . ?
C2 C1 C6 119.3(4) . . ?
C6 C1 Se1 121.2(3) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(5) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(4) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 Se1 121.8(3) . . ?
C12 C7 Se1 119.2(3) . . ?
C12 C7 C8 118.8(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 N1 122.3(3) . . ?
C9 C10 C11 118.0(3) . . ?
C11 C10 N1 119.7(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 121.3(3) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
O1 C13 N1 125.5(3) . . ?
O1 C13 C14 126.3(3) . . ?
N1 C13 C14 108.2(3) . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C13 C14 C15 105.7(3) . . ?
H14A C14 H14B 108.7 . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
C14 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C14 C15 C16 105.0(3) . . ?
H15A C15 H15B 108.8 . . ?
C16 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
N1 C16 C15 104.6(2) . . ?
N1 C16 H16B 110.8 . . ?
N1 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C15 C16 H16A 110.8 . . ?
H16B C16 H16A 108.9 . . ?

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
Se1 C1 C2 C3 178.9(3) . . . . ?
Se1 C1 C6 C5 -178.8(3) . . . . ?
Se1 C7 C8 C9 -174.9(2) . . . . ?
Se1 C7 C12 C11 174.4(2) . . . . ?
O1 C13 C14 C15 170.3(3) . . . . ?
N1 C10 C11 C12 -179.7(3) . . . . ?
N1 C13 C14 C15 -11.0(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 -1.0(7) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C8 C7 C12 C11 -1.4(5) . . . . ?
C8 C9 C10 N1 179.2(3) . . . . ?
C8 C9 C10 C11 -1.8(4) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 N1 C13 O1 5.8(5) . . . . ?
C10 N1 C13 C14 -172.9(3) . . . . ?
C10 N1 C16 C15 -174.8(3) . . . . ?
C10 C11 C12 C7 0.3(5) . . . . ?
C12 C7 C8 C9 0.9(5) . . . . ?
C13 N1 C10 C9 -24.1(4) . . . . ?
C13 N1 C10 C11 156.9(3) . . . . ?
C13 N1 C16 C15 13.2(4) . . . . ?
C13 C14 C15 C16 18.5(3) . . . . ?
C14 C15 C16 N1 -19.1(3) . . . . ?
C16 N1 C10 C9 165.1(3) . . . . ?
C16 N1 C10 C11 -13.9(4) . . . . ?
C16 N1 C13 O1 177.3(3) . . . . ?
C16 N1 C13 C14 -1.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
