# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_it2212c_auto
_database_code_depnum_ccdc_archive 'CCDC 2373646'
loop_
_audit_author_name
_audit_author_address
'Tsutomu Ishi-i'
;National Institute of Technology, Kurume College
Japan
;
_audit_update_record             
;
2024-07-26 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2022-12-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 Br2 N2 O2 Se'
_chemical_formula_sum            'C8 H6 Br2 N2 O2 Se'
_chemical_formula_weight         400.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Se N C O H'
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'
Br Br -0.6763 1.2805 '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           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                   13.6998(2)
_cell_length_b                   4.35670(10)
_cell_length_c                   18.0116(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.419(2)
_cell_angle_gamma                90
_cell_volume                     1074.71(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5937
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.9420
_cell_measurement_theta_min      3.2100
_shelx_estimated_absorpt_T_max   0.550
_shelx_estimated_absorpt_T_min   0.164
_exptl_absorpt_coefficient_mu    13.316
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -3 1 0.1031
7 0 6 0.0299
-7 0 -6 0.0299
1 -3 -2 0.1029
-5 0 10 0.0213
0 3 0 0.1040
5 0 -10 0.0209

_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.051
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0279 -2.7928 1.3076 -0.0570 -0.0581 0.9967
7.4709 0.1465 6.0646 0.6878 0.7258 -0.0092
-7.4344 0.0279 -6.1691 -0.6868 -0.7249 -0.0532
1.3975 -2.7528 -1.9991 0.2694 -0.2571 0.9281
-4.7625 -0.2935 9.9500 -0.7023 0.6649 0.2544
-0.3140 2.8262 -0.2667 -0.1098 0.1060 -0.9883
4.8149 0.0498 -9.9794 0.7155 -0.6776 -0.1700

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8169
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.257
_diffrn_reflns_theta_min         3.227
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -139.00 -91.00   0.50    0.05    --  -61.13-125.00-180.00   96
  2  ω   -139.00 -91.00   0.50    0.05    --  -61.13-125.00 120.00   96
  3  ω   -175.00 -54.00   0.50    0.05    -- -104.00 -12.00  35.00  242
  4  ω   -114.00  21.00   0.50    0.05    --  -61.13 -12.00  35.00  270
  5  ω    -73.00 -25.00   0.50    0.05    -- -104.00  77.00-150.00   96
  6  ω    -73.00 -25.00   0.50    0.05    -- -104.00  77.00-120.00   96
  7  ω    -73.00 -25.00   0.50    0.05    -- -104.00  77.00-180.00   96
  8  ω    -55.00  27.00   0.50    0.05    --    0.00 -57.00-180.00  164
  9  ω    103.00 178.00   0.50    0.05    --  122.25 111.00-120.00  150
 10  ω    -16.00  33.00   0.50    0.05    --    0.00 -77.00 -90.00   98
 11  ω    -88.00 -54.00   0.50    0.05    --    0.00 -12.00  35.00   68
 12  ω    -16.00  33.00   0.50    0.05    --    0.00 -77.00  60.00   98
 13  ω     18.00 101.00   0.50    0.05    --   61.13-125.00 -30.00  166
 14  ω     38.00  93.00   0.50    0.05    --  122.25 -94.00   0.00  110
 15  ω     42.00  92.00   0.50    0.05    --  122.25-111.00 -60.00  100
 16  ω     38.00  93.00   0.50    0.05    --  122.25 -93.00 -23.88  110
 17  ω     38.00  93.00   0.50    0.05    --  122.25 -94.00 -30.00  110
 18  ω     38.00  93.00   0.50    0.05    --  122.25 -94.00 -60.00  110
 19  ω     42.00  92.00   0.50    0.05    --  122.25-111.00 -90.00  100
 20  ω    -22.00  21.00   0.50    0.05    --   61.13 -38.00-180.00   86
 21  ω     40.00  93.00   0.50    0.05    --  122.25 -85.00 -99.11  106
 22  ω     38.00  93.00   0.50    0.05    --  122.25 -94.00-120.00  110
 23  ω     43.00  77.00   0.50    0.05    --  122.25 -77.00-180.00   68
 24  ω    -25.00 119.00   0.50    0.05    --   61.13  12.00-152.00  288
 25  ω     58.00 178.00   0.50    0.05    --  122.25  12.00-152.00  240
 26  ω     95.00 178.00   0.50    0.05    --  122.25  61.00-150.00  166
 27  ω     95.00 178.00   0.50    0.05    --  122.25  45.00-120.00  166
 28  ω     43.00 131.00   0.50    0.05    --  122.25  15.00   0.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1084609000
_diffrn_orient_matrix_UB_12      -0.0286340000
_diffrn_orient_matrix_UB_13      -0.0195094000
_diffrn_orient_matrix_UB_21      0.0293807000
_diffrn_orient_matrix_UB_22      0.0485336000
_diffrn_orient_matrix_UB_23      0.0823200000
_diffrn_orient_matrix_UB_31      -0.0048859000
_diffrn_orient_matrix_UB_32      -0.3490162000
_diffrn_orient_matrix_UB_33      0.0129365000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2196
_reflns_number_total             2299
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.794
_refine_diff_density_min         -1.124
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.099
_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)+(0.0559P)²+0.7542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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
Br1 Br 0.08879(2) 0.00966(7) 0.71034(2) 0.02056(11) Uani 1 1 d . . . . .
Br2 Br 0.38437(2) 0.85010(7) 0.50982(2) 0.02161(11) Uani 1 1 d . . . . .
Se1 Se 0.08740(2) 0.25847(8) 0.44413(2) 0.02159(12) Uani 1 1 d . . . . .
O1 O 0.28904(15) 0.2884(5) 0.75481(11) 0.0207(4) Uani 1 1 d . . . . .
O2 O 0.40499(15) 0.6654(5) 0.67444(11) 0.0206(4) Uani 1 1 d . . . . .
N1 N 0.08001(18) 0.1422(6) 0.53954(14) 0.0201(5) Uani 1 1 d . . . . .
N2 N 0.1944(2) 0.4904(6) 0.45967(14) 0.0220(5) Uani 1 1 d . . . . .
C1 C 0.1552(2) 0.2736(7) 0.57557(16) 0.0176(5) Uani 1 1 d . . . . .
C2 C 0.1771(2) 0.2324(7) 0.65291(17) 0.0182(6) Uani 1 1 d . . . . .
C3 C 0.2605(2) 0.3559(7) 0.68342(15) 0.0168(5) Uani 1 1 d . . . . .
C4 C 0.3239(2) 0.5443(7) 0.63903(16) 0.0184(6) Uani 1 1 d . . . . .
C5 C 0.3019(2) 0.6030(7) 0.56668(16) 0.0189(6) Uani 1 1 d . . . . .
C6 C 0.2184(2) 0.4650(7) 0.53145(16) 0.0187(6) Uani 1 1 d . . . . .
C7 C 0.2750(2) 0.5286(8) 0.80867(17) 0.0252(6) Uani 1 1 d . . . . .
H7A H 0.305983 0.717800 0.791609 0.038 Uiso 1 1 calc R U . . .
H7B H 0.304542 0.467022 0.856495 0.038 Uiso 1 1 calc R U . . .
H7C H 0.204976 0.564120 0.814481 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4917(2) 0.4808(8) 0.66483(18) 0.0254(7) Uani 1 1 d . . . . .
H8A H 0.512614 0.496894 0.613341 0.038 Uiso 1 1 calc R U . . .
H8B H 0.477119 0.265954 0.676277 0.038 Uiso 1 1 calc R U . . .
H8C H 0.543990 0.554603 0.698373 0.038 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
Br1 C2 1.881(3) . ?
Br2 C5 1.882(3) . ?
Se1 N1 1.797(3) . ?
Se1 N2 1.796(3) . ?
O1 C3 1.367(3) . ?
O1 C7 1.443(4) . ?
O2 C4 1.373(3) . ?
O2 C8 1.448(4) . ?
N1 C1 1.333(4) . ?
N2 C6 1.331(4) . ?
C1 C2 1.429(4) . ?
C1 C6 1.453(4) . ?
C2 C3 1.365(4) . ?
C3 C4 1.450(4) . ?
C4 C5 1.354(4) . ?
C5 C6 1.428(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Se1 N1 94.29(12) . . ?
C3 O1 C7 115.9(2) . . ?
C4 O2 C8 112.8(2) . . ?
C1 N1 Se1 106.5(2) . . ?
C6 N2 Se1 106.6(2) . . ?
N1 C1 C2 124.2(3) . . ?
N1 C1 C6 116.3(3) . . ?
C2 C1 C6 119.5(3) . . ?
C1 C2 Br1 118.6(2) . . ?
C3 C2 Br1 121.7(2) . . ?
C3 C2 C1 119.8(3) . . ?
O1 C3 C4 118.6(2) . . ?
C2 C3 O1 120.7(3) . . ?
C2 C3 C4 120.5(3) . . ?
O2 C4 C3 116.8(2) . . ?
C5 C4 O2 122.2(3) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 Br2 120.6(2) . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 Br2 119.0(2) . . ?
N2 C6 C1 116.3(3) . . ?
N2 C6 C5 124.9(3) . . ?
C5 C6 C1 118.7(3) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_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 2.839
_oxdiff_exptl_absorpt_empirical_full_min 0.637
