# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_WWZ2023041201_auto
_database_code_depnum_ccdc_archive 'CCDC 2429784'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2025-03-09 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.02.24 svn.r684696ac for OlexSys, GUI svn.r6476)
;
_chemical_formula_moiety         'C6 H4 N2 Se, C8 H5 N O6'
_chemical_formula_sum            'C14 H9 N3 O6 Se'
_chemical_formula_weight         394.203
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84090 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2

_symmetry_Int_Tables_number      13
_cell_length_a                   11.3555(4)
_cell_length_b                   9.1502(3)
_cell_length_c                   7.1692(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.648(5)
_cell_angle_gamma                90
_cell_volume                     734.38(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2894
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7560
_cell_measurement_theta_min      4.2550
_exptl_absorpt_coefficient_mu    2.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_description       block
_exptl_crystal_F_000             392.270
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.9610
_diffrn_reflns_Laue_measured_fraction_max 0.8717
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7626
_diffrn_reflns_point_group_measured_fraction_full 0.9610
_diffrn_reflns_point_group_measured_fraction_max 0.8717
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         3.64
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9610
_diffrn_measured_fraction_theta_max 0.8717
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  42.00   1.00    4.46    --   17.09  77.00  60.00   52
  2  ω      0.00  84.00   1.00    4.46    --   17.09  57.00  30.00   84
  3  ω     39.00  89.00   1.00    4.46    --   17.09 178.00-180.00   50
  4  ω     39.00  89.00   1.00    4.46    --   17.09 178.00 -90.00   50
  5  ω     -2.00  86.00   1.00    4.46    --   17.09  38.00  60.00   88
  6  ω    -10.00  42.00   1.00    4.46    --   17.09  77.00-180.00   52
  7  ω    -10.00  42.00   1.00    4.46    --   17.09  77.00-120.00   52
  8  ω    -52.00  -2.00   1.00    4.46    --   17.09 -38.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0165948000
_diffrn_orient_matrix_UB_12      0.0650636000
_diffrn_orient_matrix_UB_13      0.0515279000
_diffrn_orient_matrix_UB_21      -0.0566694000
_diffrn_orient_matrix_UB_22      0.0306300000
_diffrn_orient_matrix_UB_23      -0.0353878000
_diffrn_orient_matrix_UB_31      -0.0228537000
_diffrn_orient_matrix_UB_32      -0.0288839000
_diffrn_orient_matrix_UB_33      0.0786227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1484
_reflns_number_total             1733
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.7491
_refine_diff_density_min         -0.4957
_refine_diff_density_rms         0.1089
_refine_ls_d_res_high            0.7284
_refine_ls_d_res_low             5.5974
_refine_ls_goodness_of_fit_ref   1.0756
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.0756
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+0.2925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0829
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Se1 Se 0.5 0.66492(4) 0.25 0.03829(15) Uani 1.000000 2 S T P
N1 N 0.60858(19) 0.7995(2) 0.3399(3) 0.0351(5) Uani 1.000000 1 . . .
C1 C 0.5601(2) 0.9309(3) 0.2990(4) 0.0313(6) Uani 1.000000 1 . . .
C2 C 0.6206(2) 1.0662(3) 0.3468(4) 0.0380(6) Uani 1.000000 1 . . .
H2 H 0.6991(2) 1.0678(3) 0.4102(4) 0.0456(7) Uiso 1.000000 1 R . .
C3 C 0.5608(3) 1.1916(3) 0.2975(4) 0.0427(7) Uani 1.000000 1 . . .
H3 H 0.5996(3) 1.2804(3) 0.3258(4) 0.0513(8) Uiso 1.000000 1 R . .
O1 O 0.80230(17) 0.69948(19) 0.5770(3) 0.0450(5) Uani 1.000000 1 . . .
H1 H 0.7462(17) 0.73793(19) 0.507(4) 0.0676(7) Uiso 1.000000 1 GR . .
O2 O 0.70508(17) 0.4941(2) 0.4788(3) 0.0480(5) Uani 1.000000 1 . . .
O3 O 0.9091(3) 0.0300(3) 0.6791(6) 0.1100(13) Uani 1.000000 1 . . .
N2 N 1.0 0.0921(4) 0.75 0.0717(13) Uani 1.000000 2 S T P
C4 C 0.8994(2) 0.4777(3) 0.6636(4) 0.0297(5) Uani 1.000000 1 . . .
C5 C 1.0 0.5532(4) 0.75 0.0291(7) Uani 1.000000 2 S T P
H5 H 1.0 0.6548(4) 0.75 0.0349(9) Uiso 1.000000 2 RS T P
C6 C 1.0 0.2538(4) 0.75 0.0409(9) Uani 1.000000 2 S T P
C7 C 0.8991(2) 0.3260(3) 0.6634(4) 0.0390(6) Uani 1.000000 1 . . .
H7 H 0.8322(2) 0.2743(3) 0.6060(4) 0.0468(8) Uiso 1.000000 1 R . .
C8 C 0.7919(2) 0.5563(3) 0.5642(4) 0.0325(6) Uani 1.000000 1 . . .


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 1.785(2) 2_655 ?
Se1 N1 1.785(2) . ?
N1 C1 1.335(3) . ?
C1 C1 1.427(5) 2_655 ?
C1 C2 1.429(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.350(4) . ?
C3 C3 1.434(6) 2_655 ?
C3 H3 0.9300 . ?
O1 H1 0.8200 . ?
O1 C8 1.317(3) . ?
O2 C8 1.212(3) . ?
O3 N2 1.213(3) . ?
N2 C6 1.479(5) . ?
C4 C5 1.389(3) . ?
C4 C7 1.388(3) . ?
C4 C8 1.491(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(3) 2_756 ?
C6 C7 1.377(3) . ?
C7 H7 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
N1 Se1 N1 92.76(14) . 2_655 ?
C1 N1 Se1 107.94(17) . 2_655 ?
C1 C1 N1 115.68(14) 2_655 . ?
C2 C1 N1 124.3(2) . . ?
H2 C2 C1 120.88(15) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.88(17) . . ?
C3 C3 C2 121.77(16) 2_655 . ?
H3 C3 C2 119.12(17) . . ?
C8 O1 H1 109.5 . . ?
O3 N2 O3 124.1(4) 2_756 . ?
C6 N2 O3 117.9(2) . . ?
C6 N2 O3 117.9(2) . 2_756 ?
C7 C4 C5 120.0(3) . . ?
C8 C4 C5 121.3(2) . . ?
C8 C4 C7 118.7(2) . . ?
C4 C5 C4 120.3(3) 2_756 . ?
H5 C5 C4 119.83(16) . . ?
H5 C5 C4 119.83(16) . 2_756 ?
C7 C6 N2 118.69(17) . . ?
C7 C6 N2 118.69(17) 2_756 . ?
C7 C6 C7 122.6(3) 2_756 . ?
C6 C7 C4 118.5(3) . . ?
H7 C7 C4 120.73(16) . . ?
H7 C7 C6 120.73(17) . . ?
O2 C8 O1 123.9(2) . . ?
C4 C8 O1 113.0(2) . . ?
C4 C8 O2 123.1(2) . . ?

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 N1 C1 C1 0.7(2) . 2_655 2_655 . ?
Se1 N1 C1 C1 0.7(2) . . . 2_655 ?
Se1 N1 C1 C2 -179.32(15) . . . . ?
Se1 N1 C1 C2 -179.32(15) 2_655 . . . ?
N1 C1 C1 N1 -0.92(18) . . 2_655 2_655 ?
N1 C1 C1 C2 179.1(3) . . 2_655 2_655 ?
N1 C1 C2 C3 -179.7(3) . . . . ?
C1 C1 C2 C3 0.3(4) 2_655 . . . ?
C1 C2 C3 C3 1.1(3) . . . 2_655 ?
C2 C3 C3 C2 -1.8(3) . . 2_655 2_655 ?
O1 C8 C4 C5 -3.1(2) . . . . ?
O1 C8 C4 C7 179.0(2) . . . . ?
O2 C8 C4 C5 176.0(2) . . . . ?
O2 C8 C4 C7 -2.0(3) . . . . ?
O3 N2 C6 C7 -2.5(3) . . . . ?
O3 N2 C6 C7 177.5(3) . . . 2_756 ?
N2 C6 C7 C4 -179.98(17) . . . . ?
N2 C6 C7 C4 -179.98(17) . . 2_756 2_756 ?
C4 C5 C4 C7 0.03(18) . . 2_756 2_756 ?
C4 C5 C4 C8 -177.89(10) . . 2_756 2_756 ?
C4 C7 C6 C7 0.0(4) . . . 2_756 ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.809
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2429789'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2025-03-09 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-09-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N2 Se, C6 H4 O4 S'
_chemical_formula_sum            'C12 H8 N2 O4 S Se'
_chemical_formula_weight         355.22
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 '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                   3.8144(11)
_cell_length_b                   22.357(7)
_cell_length_c                   15.964(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.581(9)
_cell_angle_gamma                90
_cell_volume                     1358.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6797
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.375
_cell_measurement_theta_min      2.715
_shelx_estimated_absorpt_T_max   0.702
_shelx_estimated_absorpt_T_min   0.621
_exptl_absorpt_coefficient_mu    2.931
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0838 before and 0.0582 after correction. The Ratio of minimum to maximum transmission is 0.7496. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25654
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.557
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2387
_reflns_number_total             3070
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.106
_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)+(0.0100P)²+2.3776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0791
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_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
Se1 Se 0.36937(10) 0.73827(2) 0.41247(2) 0.03865(12) Uani 1 1 d . . . . .
S1 S 0.5194(2) 0.47954(4) 0.24309(6) 0.0390(2) Uani 1 1 d . . . . .
O1 O 0.3866(10) 0.57347(14) 0.3634(2) 0.0613(9) Uani 1 1 d . . . . .
O2 O 0.5530(9) 0.65148(12) 0.28802(17) 0.0599(8) Uani 1 1 d . . . . .
O3 O 0.7696(8) 0.40038(13) 0.03678(16) 0.0514(7) Uani 1 1 d . . . . .
O4 O 0.5404(8) 0.36184(11) 0.15053(16) 0.0519(7) Uani 1 1 d . . . . .
N1 N 0.2705(8) 0.66945(13) 0.46290(18) 0.0403(7) Uani 1 1 d . . . . .
N2 N 0.2600(8) 0.78171(13) 0.50146(17) 0.0382(7) Uani 1 1 d . . . . .
C1 C 0.1635(9) 0.68207(16) 0.5385(2) 0.0333(8) Uani 1 1 d . . . . .
C2 C 0.1600(9) 0.74448(16) 0.5602(2) 0.0342(8) Uani 1 1 d . . . . .
C3 C 0.0513(10) 0.76222(18) 0.6402(2) 0.0431(9) Uani 1 1 d . . . . .
H3A H 0.052187 0.802269 0.656005 0.052 Uiso 1 1 calc R U . . .
C4 C -0.0534(10) 0.71899(19) 0.6927(2) 0.0472(10) Uani 1 1 d . . . . .
H4 H -0.129195 0.730005 0.744797 0.057 Uiso 1 1 calc R U . . .
C5 C -0.0511(10) 0.6580(2) 0.6710(2) 0.0498(10) Uani 1 1 d . . . . .
H5 H -0.124941 0.629990 0.709256 0.060 Uiso 1 1 calc R U . . .
C6 C 0.0540(10) 0.63879(18) 0.5969(2) 0.0466(10) Uani 1 1 d . . . . .
H6 H 0.055341 0.598227 0.584063 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5061(10) 0.59848(17) 0.2960(2) 0.0440(9) Uani 1 1 d . . . . .
C8 C 0.5742(9) 0.55484(16) 0.2304(2) 0.0374(8) Uani 1 1 d . . . . .
C9 C 0.6823(10) 0.56826(17) 0.1525(2) 0.0424(9) Uani 1 1 d . . . . .
H9 H 0.725037 0.606951 0.134332 0.051 Uiso 1 1 calc R U . . .
C10 C 0.7211(9) 0.51754(16) 0.1035(2) 0.0402(8) Uani 1 1 d . . . . .
H10 H 0.794033 0.518743 0.048998 0.048 Uiso 1 1 calc R U . . .
C11 C 0.6416(9) 0.46610(15) 0.1433(2) 0.0337(8) Uani 1 1 d . . . . .
C12 C 0.6438(10) 0.40431(16) 0.1120(2) 0.0386(8) Uani 1 1 d . . . . .
H1 H 0.340(13) 0.597(2) 0.390(3) 0.067(18) Uiso 1 1 d . . . . .
H3 H 0.758(15) 0.362(3) 0.020(4) 0.11(2) Uiso 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 N1 1.788(3) . ?
Se1 N2 1.791(3) . ?
S1 C8 1.710(4) . ?
S1 C11 1.714(3) . ?
O1 C7 1.319(5) . ?
O1 H1 0.70(5) . ?
O2 C7 1.206(4) . ?
O3 C12 1.323(4) . ?
O3 H3 0.90(6) . ?
O4 C12 1.211(4) . ?
N1 C1 1.328(4) . ?
N2 C2 1.328(4) . ?
C1 C2 1.438(5) . ?
C1 C6 1.424(5) . ?
C2 C3 1.424(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.356(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.408(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.342(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.467(5) . ?
C8 C9 1.367(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.357(5) . ?
C11 C12 1.469(5) . ?

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 92.48(13) . . ?
C8 S1 C11 91.13(17) . . ?
C7 O1 H1 107(4) . . ?
C12 O3 H3 109(4) . . ?
C1 N1 Se1 108.2(2) . . ?
C2 N2 Se1 108.2(2) . . ?
N1 C1 C2 115.7(3) . . ?
N1 C1 C6 124.7(3) . . ?
C6 C1 C2 119.6(3) . . ?
N2 C2 C1 115.5(3) . . ?
N2 C2 C3 124.9(3) . . ?
C3 C2 C1 119.6(3) . . ?
C2 C3 H3A 121.0 . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 H3A 121.0 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.1(4) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.2(4) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.4(4) . . ?
C5 C6 H6 120.8 . . ?
O1 C7 C8 112.8(3) . . ?
O2 C7 O1 124.3(4) . . ?
O2 C7 C8 122.9(3) . . ?
C7 C8 S1 122.8(3) . . ?
C9 C8 S1 111.7(3) . . ?
C9 C8 C7 125.5(3) . . ?
C8 C9 H9 123.8 . . ?
C8 C9 C10 112.4(3) . . ?
C10 C9 H9 123.8 . . ?
C9 C10 H10 123.4 . . ?
C11 C10 C9 113.1(3) . . ?
C11 C10 H10 123.4 . . ?
C10 C11 S1 111.6(3) . . ?
C10 C11 C12 129.1(3) . . ?
C12 C11 S1 119.3(2) . . ?
O3 C12 C11 112.4(3) . . ?
O4 C12 O3 123.9(3) . . ?
O4 C12 C11 123.7(3) . . ?

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
O1 H1 N1 0.70(5) 2.02(5) 2.722(4) 172(6) . yes
O3 H3 N2 0.90(6) 1.83(6) 2.723(4) 173(5) 2_645 yes

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 N1 C1 C2 -1.0(4) . . . . ?
Se1 N1 C1 C6 178.6(3) . . . . ?
Se1 N2 C2 C1 -0.2(4) . . . . ?
Se1 N2 C2 C3 -179.8(3) . . . . ?
S1 C8 C9 C10 -0.1(4) . . . . ?
S1 C11 C12 O3 -175.0(3) . . . . ?
S1 C11 C12 O4 5.3(5) . . . . ?
O1 C7 C8 S1 -2.5(5) . . . . ?
O1 C7 C8 C9 176.6(4) . . . . ?
O2 C7 C8 S1 178.1(3) . . . . ?
O2 C7 C8 C9 -2.8(6) . . . . ?
N1 Se1 N2 C2 -0.3(3) . . . . ?
N1 C1 C2 N2 0.8(5) . . . . ?
N1 C1 C2 C3 -179.6(3) . . . . ?
N1 C1 C6 C5 -179.4(4) . . . . ?
N2 Se1 N1 C1 0.7(3) . . . . ?
N2 C2 C3 C4 178.1(3) . . . . ?
C1 C2 C3 C4 -1.5(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C6 C1 C2 N2 -178.8(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
C7 C8 C9 C10 -179.3(4) . . . . ?
C8 S1 C11 C10 0.3(3) . . . . ?
C8 S1 C11 C12 -178.9(3) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C9 C10 C11 S1 -0.4(4) . . . . ?
C9 C10 C11 C12 178.7(4) . . . . ?
C10 C11 C12 O3 5.9(5) . . . . ?
C10 C11 C12 O4 -173.7(4) . . . . ?
C11 S1 C8 C7 179.1(3) . . . . ?
C11 S1 C8 C9 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact  Se1      ..O2       .       2.89 Ang.
RESPONSE: Checked, it's ok.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2429785'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2025-03-09 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-05-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N2 Se, C8 H5 Br O4'
_chemical_formula_sum            'C14 H9 Br N2 O4 Se'
_chemical_formula_weight         428.10
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   11.154(3)
_cell_length_b                   9.184(2)
_cell_length_c                   7.3865(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.177(9)
_cell_angle_gamma                90
_cell_volume                     746.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2636
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      24.355
_cell_measurement_theta_min      3.095
_shelx_estimated_absorpt_T_max   0.551
_shelx_estimated_absorpt_T_min   0.490
_exptl_absorpt_coefficient_mu    5.207
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1453 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.4600.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15360
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.828
_diffrn_reflns_theta_min         2.888
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1231
_reflns_number_total             1758
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1758
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.027
_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)+(0.0101P)²+1.3734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C2(H2A), C3(H3)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
Se1 Se 0.500000 0.67784(7) 0.250000 0.0523(2) Uani 1 2 d S T P . .
Br1 Br 1.000000 0.06126(9) 0.750000 0.1110(4) Uani 1 2 d S T P . .
O2 O 0.8028(3) 0.7115(3) 0.5753(5) 0.0592(9) Uani 1 1 d . . . . .
H2 H 0.744889 0.749801 0.510431 0.089 Uiso 1 1 calc R U . . .
O1 O 0.7040(3) 0.5080(4) 0.4826(5) 0.0693(10) Uani 1 1 d . . . . .
N1 N 0.6090(3) 0.8118(4) 0.3411(5) 0.0517(9) Uani 1 1 d . . . . .
C4 C 0.7917(4) 0.5691(5) 0.5647(6) 0.0485(10) Uani 1 1 d . . . . .
C5 C 0.8998(4) 0.4905(5) 0.6640(5) 0.0448(10) Uani 1 1 d . . . . .
C1 C 0.5604(4) 0.9427(5) 0.3003(6) 0.0454(10) Uani 1 1 d . . . . .
C8 C 1.000000 0.5644(6) 0.750000 0.0420(13) Uani 1 2 d S T P . .
H8 H 0.999999 0.665643 0.750001 0.050 Uiso 1 2 calc R U P . .
C6 C 0.8993(4) 0.3399(5) 0.6645(6) 0.0551(12) Uani 1 1 d . . . . .
H6 H 0.831802 0.288582 0.607639 0.066 Uiso 1 1 calc R U . . .
C2 C 0.6204(4) 1.0775(5) 0.3481(6) 0.0565(12) Uani 1 1 d . . . . .
H2A H 0.699142 1.079565 0.412425 0.068 Uiso 1 1 calc R U . . .
C7 C 1.000000 0.2675(7) 0.750000 0.0566(17) Uani 1 2 d S T P . .
C3 C 0.5609(5) 1.2009(5) 0.2985(7) 0.0642(13) Uani 1 1 d . . . . .
H3 H 0.599638 1.289391 0.327777 0.077 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 1.785(4) . ?
Se1 N1 1.785(4) 2_655 ?
Br1 C7 1.894(7) . ?
O2 H2 0.8200 . ?
O2 C4 1.315(5) . ?
O1 C4 1.205(5) . ?
N1 C1 1.333(5) . ?
C4 C5 1.493(6) . ?
C5 C8 1.374(5) . ?
C5 C6 1.384(6) . ?
C1 C1 1.432(8) 2_655 ?
C1 C2 1.425(6) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.369(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.334(7) . ?
C3 C3 1.430(10) 2_655 ?
C3 H3 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
N1 Se1 N1 92.8(2) . 2_655 ?
C4 O2 H2 109.5 . . ?
C1 N1 Se1 108.0(3) . . ?
O2 C4 C5 113.0(3) . . ?
O1 C4 O2 123.7(4) . . ?
O1 C4 C5 123.3(4) . . ?
C8 C5 C4 121.5(4) . . ?
C8 C5 C6 119.7(4) . . ?
C6 C5 C4 118.8(4) . . ?
N1 C1 C1 115.6(2) . 2_655 ?
N1 C1 C2 124.7(4) . . ?
C2 C1 C1 119.6(3) . 2_655 ?
C5 C8 C5 120.8(6) 2_756 . ?
C5 C8 H8 119.6 2_756 . ?
C5 C8 H8 119.6 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6 120.5 . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 H2A 120.8 . . ?
C6 C7 Br1 119.0(3) . . ?
C6 C7 Br1 119.0(3) 2_756 . ?
C6 C7 C6 121.9(6) 2_756 . ?
C2 C3 C3 121.9(3) . 2_655 ?
C2 C3 H3 119.0 . . ?
C3 C3 H3 119.0 2_655 . ?

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
O2 H2 N1 0.82 1.89 2.706(4) 171.5 . yes

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 N1 C1 C1 0.2(6) . . . 2_655 ?
Se1 N1 C1 C2 -179.3(4) . . . . ?
O2 C4 C5 C8 -2.2(6) . . . . ?
O2 C4 C5 C6 179.6(4) . . . . ?
O1 C4 C5 C8 177.4(4) . . . . ?
O1 C4 C5 C6 -0.8(7) . . . . ?
N1 Se1 N1 C1 -0.1(2) 2_655 . . . ?
N1 C1 C2 C3 -180.0(5) . . . . ?
C4 C5 C8 C5 -178.0(4) . . . 2_756 ?
C4 C5 C6 C7 177.7(3) . . . . ?
C5 C6 C7 Br1 -179.7(3) . . . . ?
C5 C6 C7 C6 0.3(3) . . . 2_756 ?
C1 C1 C2 C3 0.6(8) 2_655 . . . ?
C1 C2 C3 C3 0.8(9) . . . 2_655 ?
C8 C5 C6 C7 -0.5(6) . . . . ?
C6 C5 C8 C5 0.3(3) . . . 2_756 ?

_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_8_tw
_database_code_depnum_ccdc_archive 'CCDC 2429787'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2025-03-09 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-05-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N2 Se, C8 H7 N O4'
_chemical_formula_sum            'C14 H11 N3 O4 Se'
_chemical_formula_weight         364.22
_chemical_melting_point          ?
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'

_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   6.8417(7)
_cell_length_b                   12.3348(11)
_cell_length_c                   8.5209(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.207(4)
_cell_angle_gamma                90
_cell_volume                     702.83(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5526
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      72.602
_cell_measurement_theta_min      6.591
_shelx_estimated_absorpt_T_max   0.775
_shelx_estimated_absorpt_T_min   0.724
_exptl_absorpt_coefficient_mu    3.842
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1410 before and 0.0924 after correction.
The Ratio of minimum to maximum transmission is 0.5145.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            1459
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.785
_diffrn_reflns_theta_min         6.620
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1188
_reflns_number_total             1459
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         3.523
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       0.026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0821
_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)+(0.1827P)²+0.1151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2303
_refine_ls_wR_factor_ref         0.2443
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.757(15)
 0.243(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Others
 Fixed Sof: H2A(0.5) H2B(0.5)
4.a Rotating group:
 N2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C2(H2), C3(H3)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
Se1 Se 0.75612(11) 0.250000 0.49979(8) 0.0555(5) Uani 1 2 d S T P . .
O2 O 0.6712(8) 0.4605(3) 0.2993(5) 0.0750(14) Uani 1 1 d . . . . .
O1 O 0.7627(8) 0.5582(4) 0.5231(5) 0.0733(15) Uani 1 1 d . . . . .
H1 H 0.761775 0.498681 0.565771 0.110 Uiso 1 1 calc R U . . .
N1 N 0.7954(6) 0.3548(3) 0.6478(5) 0.0526(11) Uani 1 1 d . . . . .
N2 N 0.5741(12) 0.750000 -0.1384(8) 0.0720(19) Uani 1 2 d S T P . .
H2A H 0.543229 0.685450 -0.173308 0.086 Uiso 0.5 1 d R U P . .
H2B H 0.475254 0.792881 -0.173357 0.086 Uiso 0.5 1 d R U P . .
C6 C 0.7065(11) 0.750000 0.3632(9) 0.0502(16) Uani 1 2 d S T P . .
H6 H 0.739153 0.750001 0.474833 0.060 Uiso 1 2 calc R U P . .
C5 C 0.6822(7) 0.6531(4) 0.2803(6) 0.0507(12) Uani 1 1 d . . . . .
C1 C 0.8343(7) 0.3082(4) 0.7903(6) 0.0485(11) Uani 1 1 d . . . . .
C7 C 0.6370(7) 0.6528(4) 0.1129(6) 0.0541(12) Uani 1 1 d . . . . .
H7 H 0.622497 0.587106 0.058068 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7047(9) 0.5479(4) 0.3683(7) 0.0561(13) Uani 1 1 d . . . . .
C2 C 0.8723(9) 0.3650(5) 0.9405(7) 0.0634(14) Uani 1 1 d . . . . .
H2 H 0.867029 0.440280 0.942960 0.076 Uiso 1 1 calc R U . . .
C8 C 0.6130(11) 0.750000 0.0262(8) 0.0527(16) Uani 1 2 d S T P . .
C3 C 0.9159(9) 0.3074(6) 1.0787(7) 0.0684(16) Uani 1 1 d . . . . .
H3 H 0.946596 0.344206 1.176122 0.082 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 1.786(4) . ?
Se1 N1 1.786(4) 4_565 ?
O2 C4 1.226(6) . ?
O1 H1 0.8200 . ?
O1 C4 1.300(6) . ?
N1 C1 1.319(6) . ?
N2 H2A 0.86(3) 4_575 ?
N2 H2A 0.8604 . ?
N2 H2B 0.8605 . ?
N2 H2B 0.86(9) 4_575 ?
N2 C8 1.372(9) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(6) . ?
C6 C5 1.381(6) 4_575 ?
C5 C7 1.394(7) . ?
C5 C4 1.490(7) . ?
C1 C1 1.437(9) 4_565 ?
C1 C2 1.434(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.399(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.353(9) . ?
C3 C3 1.417(14) 4_565 ?
C3 H3 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
N1 Se1 N1 92.7(3) . 4_565 ?
C4 O1 H1 109.5 . . ?
C1 N1 Se1 107.8(3) . . ?
H2A N2 H2A 135.5 . 4_575 ?
H2A N2 H2B 36.3 . 4_575 ?
H2A N2 H2B 109.4 . . ?
H2A N2 H2B 109.4 4_575 4_575 ?
H2B N2 H2A 36.3 . 4_575 ?
H2B N2 H2B 75.9 . 4_575 ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2A 109.5(8) . 4_575 ?
C8 N2 H2B 108.8 . . ?
C8 N2 H2B 109(2) . 4_575 ?
C5 C6 H6 120.0 4_575 . ?
C5 C6 H6 120.0 . . ?
C5 C6 C5 119.9(7) 4_575 . ?
C6 C5 C7 120.2(5) . . ?
C6 C5 C4 120.5(5) . . ?
C7 C5 C4 119.3(4) . . ?
N1 C1 C1 115.8(3) . 4_565 ?
N1 C1 C2 124.9(5) . . ?
C2 C1 C1 119.2(3) . 4_565 ?
C5 C7 H7 119.6 . . ?
C5 C7 C8 120.9(5) . . ?
C8 C7 H7 119.6 . . ?
O2 C4 O1 123.9(5) . . ?
O2 C4 C5 122.3(5) . . ?
O1 C4 C5 113.8(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(6) . . ?
C3 C2 H2 120.5 . . ?
N2 C8 C7 121.0(3) . . ?
N2 C8 C7 121.0(3) . 4_575 ?
C7 C8 C7 117.9(6) . 4_575 ?
C2 C3 C3 121.6(4) . 4_565 ?
C2 C3 H3 119.2 . . ?
C3 C3 H3 119.2 4_565 . ?

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
O1 H1 N1 0.82 1.90 2.715(6) 170.4 . yes
N2 H2A O2 0.86 2.43 3.235(6) 157.1 3_665 yes
N2 H2B O2 0.86 2.44 3.235(6) 153.0 2_655 yes
C3 H3 O2 0.93 2.75 3.351(8) 123.5 1_556 yes

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 N1 C1 C1 -0.3(3) . . . 4_565 ?
Se1 N1 C1 C2 -179.2(4) . . . . ?
N1 Se1 N1 C1 0.3(4) 4_565 . . . ?
N1 C1 C2 C3 -178.2(5) . . . . ?
C6 C5 C7 C8 -0.8(9) . . . . ?
C6 C5 C4 O2 175.0(6) . . . . ?
C6 C5 C4 O1 -5.1(8) . . . . ?
C5 C6 C5 C7 1.2(10) 4_575 . . . ?
C5 C6 C5 C4 -179.0(4) 4_575 . . . ?
C5 C7 C8 N2 178.1(6) . . . . ?
C5 C7 C8 C7 0.3(10) . . . 4_575 ?
C1 C1 C2 C3 2.9(7) 4_565 . . . ?
C1 C2 C3 C3 -2.9(7) . . . 4_565 ?
C7 C5 C4 O2 -5.2(8) . . . . ?
C7 C5 C4 O1 174.7(5) . . . . ?
C4 C5 C7 C8 179.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.757(15)
2 0.243(15)

# start Validation Reply Form
_vrf_PLAT094_8_tw                
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.32 Report
RESPONSE: Twinned structure.
;
_vrf_PLAT097_8_tw                
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.52 eA-3
RESPONSE: See above.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_WWZ2023041203_auto
_database_code_depnum_ccdc_archive 'CCDC 2429786'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2025-03-09 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.02.24 svn.r684696ac for OlexSys, GUI svn.r6476)
;
_chemical_formula_moiety         'C6 H4 N2 Se, C9 H8 O4'
_chemical_formula_sum            'C15 H12 N2 O4 Se'
_chemical_formula_weight         363.233
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84090 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z
3 -x,-y,-z
4 x,-y-1/2,z

_symmetry_Int_Tables_number      11
_cell_length_a                   7.4596(4)
_cell_length_b                   12.3445(6)
_cell_length_c                   8.6525(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.155(6)
_cell_angle_gamma                90
_cell_volume                     737.94(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3003
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9980
_cell_measurement_theta_min      4.1410
_exptl_absorpt_coefficient_mu    2.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       block
_exptl_crystal_F_000             364.217
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.9964
_diffrn_reflns_Laue_measured_fraction_max 0.8928
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7916
_diffrn_reflns_point_group_measured_fraction_full 0.9964
_diffrn_reflns_point_group_measured_fraction_max 0.8928
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.27
_diffrn_reflns_theta_min         3.38
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8928
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00   3.00   1.00   12.03    --  -15.84 -38.00   0.00   88
  2  ω    -43.00  42.00   1.00   12.03    --  -15.84  77.00 -60.00   85
  3  ω    -10.00  42.00   1.00   12.03    --   17.09  77.00  30.00   52
  4  ω      0.00  84.00   1.00   12.03    --   17.09  57.00 -60.00   84
  5  ω    -52.00  36.00   1.00   12.03    --   17.09 -38.00 120.00   88
  6  ω      0.00  75.00   1.00   12.03    --   17.09  57.00-150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0420414000
_diffrn_orient_matrix_UB_12      -0.0359643000
_diffrn_orient_matrix_UB_13      -0.0406794000
_diffrn_orient_matrix_UB_21      -0.0534170000
_diffrn_orient_matrix_UB_22      -0.0435570000
_diffrn_orient_matrix_UB_23      0.0148730000
_diffrn_orient_matrix_UB_31      -0.0769540000
_diffrn_orient_matrix_UB_32      0.0105958000
_diffrn_orient_matrix_UB_33      -0.0771989000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1609
_reflns_number_total             1873
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.4788
_refine_diff_density_min         -0.4063
_refine_diff_density_rms         0.0917
_refine_ls_d_res_high            0.7269
_refine_ls_d_res_low             6.0289
_refine_ls_goodness_of_fit_ref   1.0417
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.0417
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.2254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0702
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H9a(0.5) H9b(0.5) H9c(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7)
3.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
Se1 Se 0.68917(5) 0.75 0.44718(3) 0.03961(12) Uani 1.000000 2 S T P .
N1 N 0.5709(3) 0.64574(14) 0.3020(2) 0.0393(4) Uani 1.000000 1 . . . .
C1 C 0.4566(3) 0.69180(17) 0.1609(2) 0.0342(5) Uani 1.000000 1 . . . .
C2 C 0.3380(3) 0.6354(2) 0.0146(3) 0.0492(6) Uani 1.000000 1 . . . .
H2 H 0.3362(3) 0.5601(2) 0.0122(3) 0.0591(7) Uiso 1.000000 1 R . . .
C3 C 0.2285(3) 0.6928(2) -0.1201(3) 0.0562(7) Uani 1.000000 1 . . . .
H3 H 0.1507(3) 0.6561(2) -0.2158(3) 0.0674(8) Uiso 1.000000 1 R . . .
O1 O 0.6683(3) 0.44141(13) 0.41979(19) 0.0530(5) Uani 1.000000 1 . . . .
H1 H 0.630(3) 0.50130(14) 0.3799(15) 0.0795(7) Uiso 1.000000 1 GR . . .
O2 O 0.8582(3) 0.53977(13) 0.6336(2) 0.0648(5) Uani 1.000000 1 . . . .
C4 C 0.8780(3) 0.34710(17) 0.6528(2) 0.0343(5) Uani 1.000000 1 . . . .
C5 C 1.0154(3) 0.34611(19) 0.8158(3) 0.0415(5) Uani 1.000000 1 . . . .
H5 H 1.0610(3) 0.41148(19) 0.8697(3) 0.0498(6) Uiso 1.000000 1 R . . .
C6 C 1.0850(4) 0.25 0.8988(4) 0.0416(7) Uani 1.000000 2 S T P .
C7 C 0.8098(4) 0.25 0.5718(3) 0.0318(6) Uani 1.000000 2 S T P .
H7 H 0.7183(4) 0.25 0.4632(3) 0.0381(7) Uiso 1.000000 2 RS T P .
C8 C 0.8032(3) 0.45282(19) 0.5704(3) 0.0402(5) Uani 1.000000 1 . . . .
C9 C 1.2302(5) 0.25 1.0781(4) 0.0581(10) Uani 1.000000 2 S T P .
H9a H 1.3504(14) 0.280(2) 1.0821(6) 0.0871(15) Uiso 0.500000 1 GR . . -1
H9b H 1.1807(18) 0.2927(18) 1.1459(8) 0.0871(15) Uiso 0.500000 1 GR . . -1
H9c H 1.251(3) 0.1770(2) 1.1194(12) 0.0871(15) Uiso 0.500000 1 GR . . -1


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 1.7822(17) . ?
Se1 N1 1.7822(17) 4_575 ?
N1 C1 1.325(3) . ?
C1 C1 1.437(4) 4_575 ?
C1 C2 1.423(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.345(3) . ?
C3 C3 1.413(6) 4_575 ?
C3 H3 0.9300 . ?
O1 H1 0.8200 . ?
O1 C8 1.320(2) . ?
O2 C8 1.204(3) . ?
C4 C5 1.397(3) . ?
C4 C7 1.385(2) 4_565 ?
C4 C8 1.491(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) 4_565 ?
C6 C9 1.521(4) . ?
C7 H7 0.9300 . ?
C9 H9a 0.9600 4_565 ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9b 0.9600 4_565 ?
C9 H9c 0.9600 . ?
C9 H9c 0.9600 4_565 ?

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 N1 92.46(11) 4_575 . ?
C1 N1 Se1 108.36(14) . . ?
C1 C1 N1 115.41(11) 4_575 . ?
C2 C1 N1 125.3(2) . . ?
H2 C2 C1 120.54(14) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.54(15) . . ?
C3 C3 C2 121.77(15) 4_575 . ?
H3 C3 C2 119.12(15) . . ?
C8 O1 H1 109.5 . . ?
C7 C4 C5 119.5(2) 4_565 . ?
C8 C4 C5 119.36(19) . . ?
C8 C4 C7 121.08(18) . 4_565 ?
H5 C5 C4 119.30(13) . . ?
C6 C5 C4 121.4(2) 4_565 . ?
C6 C5 H5 119.30(13) 4_565 . ?
C5 C6 C5 118.2(3) . 4_565 ?
C9 C6 C5 120.88(13) . 4_565 ?
C9 C6 C5 120.88(13) . . ?
C4 C7 C4 119.9(3) . 4_565 ?
H7 C7 C4 120.04(13) . 4_565 ?
H7 C7 C4 120.04(13) . . ?
O2 C8 O1 123.0(2) . . ?
C4 C8 O1 112.77(18) . . ?
C4 C8 O2 124.2(2) . . ?
H9a C9 C6 109.5 . . ?
H9a C9 C6 109.5 4_565 . ?
H9a C9 H9a 46(3) . 4_565 ?
H9b C9 C6 109.5 . . ?
H9b C9 C6 109.5 4_565 . ?
H9b C9 H9a 139.5 4_565 . ?
H9b C9 H9a 109.5 . . ?
H9b C9 H9a 139.5 . 4_565 ?
H9b C9 H9a 109.5 4_565 4_565 ?
H9b C9 H9b 67(3) . 4_565 ?
H9c C9 C6 109.5 . . ?
H9c C9 C6 109.5 4_565 . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9a 66.6 4_565 . ?
H9c C9 H9a 66.6 . 4_565 ?
H9c C9 H9a 109.5 4_565 4_565 ?
H9c C9 H9b 45.9 . 4_565 ?
H9c C9 H9b 109.5 . . ?
H9c C9 H9b 109.5 4_565 4_565 ?
H9c C9 H9b 45.9 4_565 . ?
H9c C9 H9c 139.5(10) 4_565 . ?

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 N1 C1 C1 -0.16(14) . . . 4_575 ?
Se1 N1 C1 C1 0.16(14) . 4_575 4_575 . ?
Se1 N1 C1 C2 179.90(14) . . . . ?
Se1 N1 C1 C2 179.90(14) 4_575 . . . ?
N1 C1 C1 N1 0.0(3) . . 4_575 4_575 ?
N1 C1 C1 C2 -179.94(14) . . 4_575 4_575 ?
N1 C1 C2 C3 179.8(2) . . . . ?
C1 C1 C2 C3 -0.09(14) 4_575 . . . ?
C1 C2 C3 C3 0.1(3) . . . 4_575 ?
C2 C3 C3 C2 -0.0(3) . . 4_575 4_575 ?
O1 C8 C4 C5 -177.16(18) . . . . ?
O1 C8 C4 C7 1.2(2) . . . 4_565 ?
O2 C8 C4 C5 2.5(3) . . . . ?
O2 C8 C4 C7 -179.2(2) . . . 4_565 ?
C4 C5 C6 C5 0.22(14) . . 4_565 4_565 ?
C4 C5 C6 C9 -178.2(3) . . 4_565 4_565 ?
C4 C7 C4 C5 0.0(3) 4_565 . . . ?
C4 C7 C4 C8 -178.3(2) 4_565 . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.324
_oxdiff_exptl_absorpt_empirical_full_min 0.840
####################################################################### 
# 
# 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_wwz20231024-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2429788'
loop_
_audit_author_name
_audit_author_address
'Weizhou Wang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2025-03-09 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-11-06
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.02.24 svn.r684696ac for OlexSys, GUI svn.r6476)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 Br O4, C3 H2 N Se0.5'
_chemical_formula_sum            'C11 H6 Br N O4 Se0.50'
_chemical_formula_weight         335.56
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   3.89920(10)
_cell_length_b                   37.6399(13)
_cell_length_c                   7.7471(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.702(3)
_cell_angle_gamma                90
_cell_volume                     1131.38(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4895
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      25.7590
_cell_measurement_theta_min      3.7840
_shelx_estimated_absorpt_T_max   0.469
_shelx_estimated_absorpt_T_min   0.302
_exptl_absorpt_coefficient_mu    5.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14800
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         3.416
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1169
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   1.00   0.50   12.95    --  -15.68 -57.00   0.00  168
  2  ω    -42.00  44.00   0.50   12.95    --   16.78 -77.00 120.00  172
  3  ω      0.00  84.00   0.50   12.95    --   16.78  57.00 -60.00  168
  4  ω    -10.00  42.00   0.50   12.95    --   16.78  77.00-120.00  104
  5  ω    -55.00  46.00   0.50   12.95    --   16.78 -19.00 150.00  202
  6  ω    -42.00  44.00   0.50   12.95    --   16.78 -77.00   0.00  172
  7  ω      0.00  84.00   0.50   12.95    --   16.78  57.00 150.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0405594000
_diffrn_orient_matrix_UB_12      -0.0182561000
_diffrn_orient_matrix_UB_13      0.0123851000
_diffrn_orient_matrix_UB_21      -0.1610230000
_diffrn_orient_matrix_UB_22      -0.0028105000
_diffrn_orient_matrix_UB_23      0.0330947000
_diffrn_orient_matrix_UB_31      -0.0764649000
_diffrn_orient_matrix_UB_32      -0.0037640000
_diffrn_orient_matrix_UB_33      -0.0849230000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2139
_reflns_number_total             2827
_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 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.059
_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)+(0.0361P)²+1.6268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Br1 Br 0.78202(13) 0.62774(2) 0.77437(6) 0.05493(17) Uani 1 1 d . . . . .
C1 C 0.7350(11) 0.64811(10) 0.3610(6) 0.0403(10) Uani 1 1 d . . . . .
C2 C 0.6045(10) 0.61203(9) 0.4106(5) 0.0329(8) Uani 1 1 d . . . . .
C3 C 0.4768(10) 0.58901(9) 0.2780(5) 0.0342(8) Uani 1 1 d . . . . .
H3 H 0.4846 0.5956 0.1627 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3375(10) 0.55610(9) 0.3173(5) 0.0318(8) Uani 1 1 d . . . . .
C5 C 0.3308(11) 0.54611(10) 0.4888(5) 0.0388(9) Uani 1 1 d . . . . .
H5 H 0.2347 0.5244 0.5154 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4653(11) 0.56810(10) 0.6197(5) 0.0387(9) Uani 1 1 d . . . . .
H6 H 0.4683 0.5609 0.7347 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5964(10) 0.60095(10) 0.5810(5) 0.0341(8) Uani 1 1 d . . . . .
C8 C 0.1913(11) 0.53213(10) 0.1767(5) 0.0376(9) Uani 1 1 d . . . . .
C9 C 1.3923(12) 0.73113(14) -0.2677(6) 0.0566(13) Uani 1 1 d . . . . .
H9 H 1.4697 0.7191 -0.3613 0.068 Uiso 1 1 calc R U . . .
C10 C 1.2844(11) 0.71249(11) -0.1371(6) 0.0447(10) Uani 1 1 d . . . . .
H10 H 1.2856 0.6878 -0.1398 0.054 Uiso 1 1 calc R U . . .
C11 C 1.1675(9) 0.73080(9) 0.0064(5) 0.0282(7) Uani 1 1 d . . . . .
N1 N 1.0545(9) 0.71562(8) 0.1446(4) 0.0390(8) Uani 1 1 d . . . . .
O1 O 0.7249(11) 0.67390(8) 0.4474(5) 0.0745(11) Uani 1 1 d . . . . .
O2 O 0.8387(10) 0.64754(7) 0.2045(4) 0.0531(9) Uani 1 1 d . . . . .
H2 H 0.9155 0.6671 0.1820 0.080 Uiso 1 1 calc R U . . .
O3 O 0.2255(10) 0.54102(8) 0.0209(4) 0.0613(10) Uani 1 1 d . . . . .
O4 O 0.0441(9) 0.50415(7) 0.2145(4) 0.0533(8) Uani 1 1 d . . . . .
Se1 Se 0.94238(16) 0.7500 0.28755(7) 0.04239(18) Uani 1 2 d S T P . .
H3A H 0.117(17) 0.5251(17) -0.054(8) 0.11(2) Uiso 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
Br1 C7 1.889(4) . ?
C1 C2 1.513(5) . ?
C1 O1 1.182(5) . ?
C1 O2 1.316(5) . ?
C2 C3 1.397(5) . ?
C2 C7 1.388(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(5) . ?
C4 C5 1.383(5) . ?
C4 C8 1.484(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(5) . ?
C8 O3 1.272(5) . ?
C8 O4 1.248(4) . ?
C9 C9 1.420(10) 4_575 ?
C9 H9 0.9300 . ?
C9 C10 1.334(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.421(5) . ?
C11 C11 1.446(6) 4_575 ?
C11 N1 1.327(5) . ?
N1 Se1 1.786(3) . ?
O2 H2 0.8200 . ?
O3 H3A 0.91(7) . ?
Se1 N1 1.786(3) 4_575 ?

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
O1 C1 C2 124.2(4) . . ?
O1 C1 O2 124.5(4) . . ?
O2 C1 C2 111.2(3) . . ?
C3 C2 C1 118.3(3) . . ?
C7 C2 C1 123.5(3) . . ?
C7 C2 C3 118.2(3) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C8 120.5(3) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 C8 119.8(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.1(4) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 Br1 123.4(3) . . ?
C6 C7 Br1 115.2(3) . . ?
C6 C7 C2 121.3(3) . . ?
O3 C8 C4 117.9(3) . . ?
O4 C8 C4 119.5(3) . . ?
O4 C8 O3 122.6(4) . . ?
C9 C9 H9 119.1 4_575 . ?
C10 C9 C9 121.7(3) . 4_575 ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C11 119.0(2) . 4_575 ?
N1 C11 C10 125.5(3) . . ?
N1 C11 C11 115.5(2) . 4_575 ?
C11 N1 Se1 108.0(2) . . ?
C1 O2 H2 109.5 . . ?
C8 O3 H3A 110(4) . . ?
N1 Se1 N1 92.9(2) 4_575 . ?

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
C1 C2 C3 C4 -176.8(4) . . . . ?
C1 C2 C7 Br1 -5.4(5) . . . . ?
C1 C2 C7 C6 178.1(4) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
C2 C3 C4 C8 178.0(4) . . . . ?
C3 C2 C7 Br1 176.3(3) . . . . ?
C3 C2 C7 C6 -0.2(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C3 C4 C8 O3 6.3(6) . . . . ?
C3 C4 C8 O4 -174.4(4) . . . . ?
C4 C5 C6 C7 2.5(6) . . . . ?
C5 C4 C8 O3 -174.8(4) . . . . ?
C5 C4 C8 O4 4.5(6) . . . . ?
C5 C6 C7 Br1 -178.6(3) . . . . ?
C5 C6 C7 C2 -1.8(6) . . . . ?
C7 C2 C3 C4 1.5(6) . . . . ?
C8 C4 C5 C6 180.0(4) . . . . ?
C9 C9 C10 C11 -0.3(5) 4_575 . . . ?
C9 C10 C11 C11 0.3(5) . . . 4_575 ?
C9 C10 C11 N1 -179.8(4) . . . . ?
C10 C11 N1 Se1 179.5(3) . . . . ?
C11 C11 N1 Se1 -0.6(3) 4_575 . . . ?
C11 N1 Se1 N1 0.7(3) . . . 4_575 ?
O1 C1 C2 C3 149.8(5) . . . . ?
O1 C1 C2 C7 -28.4(7) . . . . ?
O2 C1 C2 C3 -25.8(5) . . . . ?
O2 C1 C2 C7 156.0(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.656
