# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_try1
_database_code_depnum_ccdc_archive 'CCDC 2518317'
loop_
_audit_author_name
_audit_author_address
'Saksham Mishra'
;Indian Institution of Technology Patna
India
;
_audit_update_record             
;
2025-12-23 deposited with the CCDC.	2026-05-29 downloaded from the CCDC.
;
_audit_creation_date             2025-12-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2025/1
_chemical_name_common            'Mono-selenylated arylamide'
_chemical_name_systematic        SM-761
_chemical_formula_moiety         'C13 H10 Cl N O Se'
_chemical_formula_sum            'C13 H10 Cl N O Se'
_chemical_formula_weight         310.63
_chemical_melting_point          '478 K'
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'
Cl Cl 0.1484 0.1585 '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                   5.2679(2)
_cell_length_b                   10.7453(5)
_cell_length_c                   22.8596(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.002(2)
_cell_angle_gamma                90
_cell_volume                     1292.20(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18995
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.259
_cell_measurement_theta_min      2.095
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.094
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Cube
_exptl_crystal_F_000             616
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.259
_diffrn_reflns_theta_min         2.095
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2009
_reflns_number_total             3185
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2025/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1759
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Se01 Se 0.17826(8) 0.34542(4) 0.56409(2) 0.0598(2) Uani 1 1 d . . . . .
Cl02 Cl 0.6472(5) 0.4514(2) 0.78189(7) 0.1420(9) Uani 1 1 d . . . . .
O7 O 0.3236(6) 0.0870(3) 0.55339(14) 0.0681(8) Uani 1 1 d . . . . .
N1 N 0.7453(7) 0.0617(3) 0.55496(16) 0.0638(10) Uani 1 1 d . . . . .
H1A H 0.734721 0.010356 0.526080 0.077 Uiso 1 1 calc R U . . .
H1B H 0.891476 0.080831 0.570951 0.077 Uiso 1 1 calc R U . . .
C005 C 0.5674(8) 0.1998(4) 0.62544(17) 0.0520(9) Uani 1 1 d . . . . .
C10 C 0.4112(8) 0.3041(4) 0.62878(17) 0.0510(9) Uani 1 1 d . . . . .
C007 C 0.5364(8) 0.1114(4) 0.57479(19) 0.0545(10) Uani 1 1 d . . . . .
C008 C 0.1276(9) 0.5189(4) 0.5810(2) 0.0580(10) Uani 1 1 d . . . . .
C009 C 0.7473(10) 0.1755(4) 0.6705(2) 0.0674(12) Uani 1 1 d . . . . .
H009 H 0.851464 0.106078 0.667792 0.081 Uiso 1 1 calc R U . . .
C00A C 0.4378(10) 0.3812(4) 0.6779(2) 0.0665(12) Uani 1 1 d . . . . .
H00A H 0.336680 0.451684 0.680785 0.080 Uiso 1 1 calc R U . . .
C00B C 0.7763(11) 0.2506(5) 0.7187(2) 0.0817(15) Uani 1 1 d . . . . .
H00B H 0.899783 0.234066 0.748297 0.098 Uiso 1 1 calc R U . . .
C00C C 0.6156(13) 0.3517(4) 0.7220(2) 0.0798(16) Uani 1 1 d . . . . .
C00D C 0.2894(12) 0.6066(5) 0.5587(2) 0.0757(14) Uani 1 1 d . . . . .
H00D H 0.423698 0.581958 0.536564 0.091 Uiso 1 1 calc R U . . .
C00E C -0.0693(11) 0.5559(6) 0.6130(3) 0.0917(17) Uani 1 1 d . . . . .
H00E H -0.178364 0.497150 0.627902 0.110 Uiso 1 1 calc R U . . .
C00F C 0.050(2) 0.7667(7) 0.6016(4) 0.136(4) Uani 1 1 d . . . . .
H00F H 0.021581 0.850844 0.608374 0.163 Uiso 1 1 calc R U . . .
C00G C 0.2480(17) 0.7320(6) 0.5700(3) 0.118(3) Uani 1 1 d . . . . .
H00G H 0.356508 0.791876 0.555919 0.141 Uiso 1 1 calc R U . . .
C00H C -0.1073(16) 0.6825(9) 0.6233(4) 0.125(3) Uani 1 1 d . . . . .
H00H H -0.241478 0.708196 0.645298 0.151 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
Se01 C10 1.924(4) . ?
Se01 C008 1.926(4) . ?
Cl02 C00C 1.739(5) . ?
O7 C007 1.227(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C007 1.324(6) . ?
C005 C10 1.394(6) . ?
C005 C007 1.500(6) . ?
C005 C009 1.387(6) . ?
C10 C00A 1.397(6) . ?
C008 C00D 1.385(8) . ?
C008 C00E 1.359(7) . ?
C009 H009 0.9300 . ?
C009 C00B 1.369(6) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.377(7) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.382(7) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.392(9) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.397(10) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.354(11) . ?
C00F C00H 1.338(12) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?

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
C10 Se01 C008 99.11(17) . . ?
H1A N1 H1B 120.0 . . ?
C007 N1 H1A 120.0 . . ?
C007 N1 H1B 120.0 . . ?
C10 C005 C007 120.7(4) . . ?
C009 C005 C10 119.5(4) . . ?
C009 C005 C007 119.7(4) . . ?
C005 C10 Se01 119.9(3) . . ?
C005 C10 C00A 119.1(4) . . ?
C00A C10 Se01 120.9(3) . . ?
O7 C007 N1 122.4(4) . . ?
O7 C007 C005 120.2(4) . . ?
N1 C007 C005 117.4(4) . . ?
C00D C008 Se01 119.3(4) . . ?
C00E C008 Se01 120.6(4) . . ?
C00E C008 C00D 120.1(5) . . ?
C005 C009 H009 119.0 . . ?
C00B C009 C005 122.0(4) . . ?
C00B C009 H009 119.0 . . ?
C10 C00A H00A 120.4 . . ?
C00C C00A C10 119.2(4) . . ?
C00C C00A H00A 120.4 . . ?
C009 C00B H00B 121.2 . . ?
C009 C00B C00C 117.7(5) . . ?
C00C C00B H00B 121.2 . . ?
C00A C00C Cl02 117.9(4) . . ?
C00A C00C C00B 122.5(4) . . ?
C00B C00C Cl02 119.6(4) . . ?
C008 C00D H00D 120.5 . . ?
C008 C00D C00G 119.0(6) . . ?
C00G C00D H00D 120.5 . . ?
C008 C00E H00E 120.1 . . ?
C008 C00E C00H 119.7(7) . . ?
C00H C00E H00E 120.1 . . ?
C00G C00F H00F 119.3 . . ?
C00H C00F H00F 119.3 . . ?
C00H C00F C00G 121.3(7) . . ?
C00D C00G H00G 120.0 . . ?
C00F C00G C00D 119.9(7) . . ?
C00F C00G H00G 120.0 . . ?
C00E C00H H00H 120.0 . . ?
C00F C00H C00E 119.9(8) . . ?
C00F C00H H00H 120.0 . . ?

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
Se01 C10 C00A C00C -176.8(4) . . . . ?
Se01 C008 C00D C00G 178.5(4) . . . . ?
Se01 C008 C00E C00H -178.1(5) . . . . ?
C005 C10 C00A C00C -0.7(7) . . . . ?
C005 C009 C00B C00C 1.2(8) . . . . ?
C10 C005 C007 O7 -37.1(6) . . . . ?
C10 C005 C007 N1 143.1(4) . . . . ?
C10 C005 C009 C00B 0.4(7) . . . . ?
C10 C00A C00C Cl02 178.9(4) . . . . ?
C10 C00A C00C C00B 2.4(9) . . . . ?
C007 C005 C10 Se01 -6.7(5) . . . . ?
C007 C005 C10 C00A 177.1(4) . . . . ?
C007 C005 C009 C00B -177.4(5) . . . . ?
C008 C00D C00G C00F -1.0(8) . . . . ?
C008 C00E C00H C00F 0.2(11) . . . . ?
C009 C005 C10 Se01 175.5(3) . . . . ?
C009 C005 C10 C00A -0.7(6) . . . . ?
C009 C005 C007 O7 140.6(5) . . . . ?
C009 C005 C007 N1 -39.1(6) . . . . ?
C009 C00B C00C Cl02 -179.1(5) . . . . ?
C009 C00B C00C C00A -2.6(9) . . . . ?
C00D C008 C00E C00H -0.2(8) . . . . ?
C00E C008 C00D C00G 0.6(7) . . . . ?
C00G C00F C00H C00E -0.7(12) . . . . ?
C00H C00F C00G C00D 1.1(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sm_802_0m
_database_code_depnum_ccdc_archive 'CCDC 2537738'
loop_
_audit_author_name
_audit_author_address
'Saksham Mishra'
;Indian Institute of Technology Patna
India
;
_audit_update_record             
;
2026-03-14 deposited with the CCDC.	2026-05-29 downloaded from the CCDC.
;
_audit_creation_date             2026-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2025/1
_chemical_name_common            ?
_chemical_name_systematic        
4-(phenylselanyl)benzo[d][1,3]dioxole-5-carboxamide
_chemical_formula_moiety         'C14 H11 N O3 Se'
_chemical_formula_sum            'C14 H11 N O3 Se'
_chemical_formula_weight         320.20
_chemical_melting_point          461
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      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                   5.0631(13)
_cell_length_b                   8.940(2)
_cell_length_c                   15.051(4)
_cell_angle_alpha                97.607(12)
_cell_angle_beta                 91.807(12)
_cell_angle_gamma                105.462(12)
_cell_volume                     649.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4598
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.894
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3784
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1532 before and 0.0982 after correction.
The Ratio of minimum to maximum transmission is 0.5074.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9617
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.575
_diffrn_reflns_theta_min         2.922
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2239
_reflns_number_total             3311
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2025/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.135
_refine_diff_density_min         -1.577
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.070(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2025/1 (Sheldrick 2025)'
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      1.261
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.2127
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00D,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00C), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I),
 C00J(H00J)
2.c X=CH2 refined with riding coordinates:
 N004(H00A,H00B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Se01 Se 0.64146(10) 0.62136(6) 0.75207(3) 0.0517(3) Uani 1 1 d . . . . .
O002 O 0.6379(7) 0.9214(5) 0.8980(2) 0.0541(10) Uani 1 1 d . . . . .
O003 O 0.4578(11) 0.6444(6) 0.5518(3) 0.0815(15) Uani 1 1 d . . . . .
N004 N 0.1991(8) 0.9190(6) 0.9134(3) 0.0600(13) Uani 1 1 d . . . . .
H00A H 0.226858 0.943545 0.970735 0.072 Uiso 1 1 calc R U . . .
H00B H 0.038131 0.905092 0.887989 0.072 Uiso 1 1 calc R U . . .
O005 O 0.2121(12) 0.7913(7) 0.4882(3) 0.0878(16) Uani 1 1 d . . . . .
C006 C 0.4046(10) 0.9025(6) 0.8640(3) 0.0429(11) Uani 1 1 d . . . . .
C007 C 0.3425(9) 0.8682(5) 0.7640(3) 0.0400(11) Uani 1 1 d . . . . .
C008 C 0.4468(9) 0.7591(6) 0.7092(3) 0.0415(11) Uani 1 1 d . . . . .
C009 C 0.1905(11) 0.9536(6) 0.7250(4) 0.0487(12) Uani 1 1 d . . . . .
H009 H 0.121024 1.023454 0.762246 0.058 Uiso 1 1 calc R U . . .
C00A C 0.3284(12) 0.4821(6) 0.7928(4) 0.0538(13) Uani 1 1 d . . . . .
C00B C 0.1375(13) 0.9391(7) 0.6322(4) 0.0586(15) Uani 1 1 d . . . . .
H00C H 0.038964 0.999057 0.606945 0.070 Uiso 1 1 calc R U . . .
C00C C 0.3883(12) 0.7452(7) 0.6186(3) 0.0517(13) Uani 1 1 d . . . . .
C00D C 0.2368(13) 0.8335(8) 0.5810(4) 0.0567(14) Uani 1 1 d . . . . .
C00E C 0.1174(13) 0.3854(7) 0.7316(5) 0.0668(16) Uani 1 1 d . . . . .
H00E H 0.128598 0.387262 0.670206 0.080 Uiso 1 1 calc R U . . .
C00F C -0.1036(17) 0.2889(8) 0.7633(8) 0.095(3) Uani 1 1 d . . . . .
H00F H -0.244397 0.226281 0.722637 0.114 Uiso 1 1 calc R U . . .
C00G C 0.365(2) 0.6796(12) 0.4694(5) 0.110(3) Uani 1 1 d . . . . .
H00D H 0.250263 0.584996 0.433614 0.132 Uiso 1 1 calc R U . . .
H00G H 0.520768 0.722285 0.435603 0.132 Uiso 1 1 calc R U . . .
C00H C -0.125(3) 0.2810(12) 0.8534(10) 0.121(4) Uani 1 1 d . . . . .
H00H H -0.280797 0.215939 0.873392 0.145 Uiso 1 1 calc R U . . .
C00I C 0.311(2) 0.4736(10) 0.8834(5) 0.096(3) Uani 1 1 d . . . . .
H00I H 0.449782 0.535916 0.924999 0.115 Uiso 1 1 calc R U . . .
C00J C 0.079(3) 0.3679(14) 0.9118(8) 0.134(5) Uani 1 1 d . . . . .
H00J H 0.068417 0.358865 0.972555 0.161 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
Se01 C008 1.929(5) . ?
Se01 C00A 1.911(6) . ?
O002 C006 1.233(6) . ?
O003 C00C 1.378(6) . ?
O003 C00G 1.416(8) . ?
N004 H00A 0.8600 . ?
N004 H00B 0.8600 . ?
N004 C006 1.325(6) . ?
O005 C00D 1.390(7) . ?
O005 C00G 1.425(10) . ?
C006 C007 1.501(6) . ?
C007 C008 1.414(6) . ?
C007 C009 1.387(7) . ?
C008 C00C 1.368(7) . ?
C009 H009 0.9300 . ?
C009 C00B 1.397(7) . ?
C00A C00E 1.404(9) . ?
C00A C00I 1.380(8) . ?
C00B H00C 0.9300 . ?
C00B C00D 1.349(9) . ?
C00C C00D 1.395(8) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.361(10) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.373(15) . ?
C00G H00D 0.9700 . ?
C00G H00G 0.9700 . ?
C00H H00H 0.9300 . ?
C00H C00J 1.335(17) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.417(14) . ?
C00J H00J 0.9300 . ?

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
C00A Se01 C008 96.1(2) . . ?
C00C O003 C00G 106.3(5) . . ?
H00A N004 H00B 120.0 . . ?
C006 N004 H00A 120.0 . . ?
C006 N004 H00B 120.0 . . ?
C00D O005 C00G 106.3(5) . . ?
O002 C006 N004 121.8(5) . . ?
O002 C006 C007 121.5(4) . . ?
N004 C006 C007 116.6(4) . . ?
C008 C007 C006 122.0(4) . . ?
C009 C007 C006 118.0(4) . . ?
C009 C007 C008 119.9(4) . . ?
C007 C008 Se01 125.4(4) . . ?
C00C C008 Se01 118.2(4) . . ?
C00C C008 C007 116.3(5) . . ?
C007 C009 H009 118.6 . . ?
C007 C009 C00B 122.8(5) . . ?
C00B C009 H009 118.6 . . ?
C00E C00A Se01 120.9(5) . . ?
C00I C00A Se01 119.7(5) . . ?
C00I C00A C00E 119.3(7) . . ?
C009 C00B H00C 121.8 . . ?
C00D C00B C009 116.5(5) . . ?
C00D C00B H00C 121.8 . . ?
O003 C00C C00D 109.8(5) . . ?
C008 C00C O003 127.4(5) . . ?
C008 C00C C00D 122.7(5) . . ?
O005 C00D C00C 108.6(5) . . ?
C00B C00D O005 129.5(6) . . ?
C00B C00D C00C 121.9(5) . . ?
C00A C00E H00E 120.4 . . ?
C00F C00E C00A 119.2(8) . . ?
C00F C00E H00E 120.4 . . ?
C00E C00F H00F 118.9 . . ?
C00E C00F C00H 122.1(9) . . ?
C00H C00F H00F 118.9 . . ?
O003 C00G O005 108.5(6) . . ?
O003 C00G H00D 110.0 . . ?
O003 C00G H00G 110.0 . . ?
O005 C00G H00D 110.0 . . ?
O005 C00G H00G 110.0 . . ?
H00D C00G H00G 108.4 . . ?
C00F C00H H00H 120.4 . . ?
C00J C00H C00F 119.2(10) . . ?
C00J C00H H00H 120.4 . . ?
C00A C00I H00I 120.7 . . ?
C00A C00I C00J 118.7(9) . . ?
C00J C00I H00I 120.7 . . ?
C00H C00J C00I 121.5(10) . . ?
C00H C00J H00J 119.3 . . ?
C00I C00J H00J 119.3 . . ?

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
Se01 C008 C00C O003 -1.5(8) . . . . ?
Se01 C008 C00C C00D 176.7(5) . . . . ?
Se01 C00A C00E C00F -179.3(5) . . . . ?
Se01 C00A C00I C00J -179.2(8) . . . . ?
O002 C006 C007 C008 43.8(7) . . . . ?
O002 C006 C007 C009 -132.6(6) . . . . ?
O003 C00C C00D O005 -1.1(7) . . . . ?
O003 C00C C00D C00B 178.5(6) . . . . ?
N004 C006 C007 C008 -139.4(5) . . . . ?
N004 C006 C007 C009 44.2(7) . . . . ?
C006 C007 C008 Se01 7.8(7) . . . . ?
C006 C007 C008 C00C -176.3(5) . . . . ?
C006 C007 C009 C00B 175.4(5) . . . . ?
C007 C008 C00C O003 -177.7(6) . . . . ?
C007 C008 C00C C00D 0.6(8) . . . . ?
C007 C009 C00B C00D 1.6(9) . . . . ?
C008 C007 C009 C00B -1.1(8) . . . . ?
C008 C00C C00D O005 -179.6(6) . . . . ?
C008 C00C C00D C00B 0.0(10) . . . . ?
C009 C007 C008 Se01 -175.9(4) . . . . ?
C009 C007 C008 C00C 0.0(7) . . . . ?
C009 C00B C00D O005 178.5(6) . . . . ?
C009 C00B C00D C00C -1.0(10) . . . . ?
C00A C00E C00F C00H -1.1(11) . . . . ?
C00A C00I C00J C00H -2.1(18) . . . . ?
C00C O003 C00G O005 -6.4(10) . . . . ?
C00D O005 C00G O003 5.7(10) . . . . ?
C00E C00A C00I C00J -0.6(12) . . . . ?
C00E C00F C00H C00J -1.6(16) . . . . ?
C00F C00H C00J C00I 3.1(19) . . . . ?
C00G O003 C00C C008 -177.0(7) . . . . ?
C00G O003 C00C C00D 4.6(8) . . . . ?
C00G O005 C00D C00B 177.6(8) . . . . ?
C00G O005 C00D C00C -2.9(8) . . . . ?
C00I C00A C00E C00F 2.1(9) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
