# 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_dr-7
_database_code_depnum_ccdc_archive 'CCDC 2371307'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-10-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_dr-7                
;
PROBLEM: Short Inter D...A Contact  Se1      ..N1       .       2.84 Ang.  
RESPONSE: This is due to the unique crystal structure.
;
_audit_creation_date             2024-05-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 Br N5 Se'
_chemical_formula_sum            'C9 H10 Br N5 Se'
_chemical_formula_weight         347.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H10BrN5Se
_chemical_oxdiff_usercomment     DR-7
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'
Se Se -0.7943 1.1372 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.5188(3)
_cell_length_b                   6.73250(10)
_cell_length_c                   20.1942(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.2020(10)
_cell_angle_gamma                90
_cell_volume                     4402.96(9)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    20393
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.8130
_cell_measurement_theta_min      2.7380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.714
_exptl_absorpt_correction_T_max  -0.010
_exptl_absorpt_correction_T_min  10000000.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.117a (Rigaku Oxford Diffraction, 2024)
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            red
_exptl_crystal_density_diffrn    2.094
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -4 0 0.2516
21 0 -2 0.0365
2 -4 3 0.2459
-2 4 -3 0.1975
-21 0 2 0.0466
15 0 8 0.0437
-15 0 -8 0.0418
-6 0 13 0.0384
6 0 -13 0.0269
-17 0 9 0.0350

_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.067
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
-0.6381 -4.3680 0.0089 -0.0605 -0.2405 0.9688
21.0614 0.2799 -1.7236 0.8935 -0.4245 -0.1468
2.3256 -4.2221 2.9200 0.1650 -0.0817 0.9829
-2.3100 4.2224 -2.9213 -0.1643 0.0814 -0.9830
-20.9616 -0.4862 1.8672 -0.8860 0.4208 0.1949
15.1816 0.2757 8.2002 0.9410 0.3342 0.0527
-15.2688 -0.4601 -8.0713 -0.9422 -0.3348 -0.0092
-5.7939 0.4271 12.8137 0.1453 0.9768 0.1573
5.7894 -0.4575 -12.8046 -0.1455 -0.9779 -0.1504
-16.8962 -0.0136 8.7745 -0.4831 0.8505 0.2080

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.389
_diffrn_reflns_theta_min         2.729
_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 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  26.00   0.50    1.00    --    0.00 -19.00  -1.00  226
  2  ω    -27.00  83.00   0.50    1.00    --    0.00  19.00 166.00  220
  3  ω    -87.00  26.00   0.50    1.00    --    0.00 -19.00  -1.00  226
  4  ω    -27.00  21.00   0.50    2.00    --  -61.62  19.00 166.00   96
  5  ω   -147.00   7.00   0.50    2.00    --  -61.62 -19.00  -1.00  308
  6  ω   -177.00 -33.00   0.50    3.50    -- -101.75 -19.00  -1.00  288
  7  ω     47.00 178.00   0.50    3.50    --  123.25  19.00 166.00  262
  8  ω     -1.00  46.00   0.50    1.00    --    0.00 -99.00-180.00   94
  9  ω    -86.00 -13.00   0.50    2.00    --  -61.62 125.00 150.00  146
 10  ω    -14.00 144.00   0.50    2.00    --   61.62  19.00 166.00  316
 11  ω     34.00 112.00   0.50    2.00    --   61.62-125.00  60.00  156
 12  ω    -71.00 -27.00   0.50    3.50    -- -101.75  61.00   0.00   88
 13  ω    -51.00 -21.00   0.50    3.50    -- -101.75  45.00 -30.00   60
 14  ω    -71.00 -27.00   0.50    3.50    -- -101.75  61.00 -60.00   88
 15  ω     47.00 105.00   0.50    3.50    --  123.25 -77.00  30.00  116
 16  ω    103.00 178.00   0.50    3.50    --  123.25 111.00 -60.00  150
 17  ω     91.00 178.00   0.50    3.50    --  123.25  45.00-180.00  174
 18  ω     41.00 105.00   0.50    3.50    --  123.25 -95.00-150.00  128
 19  ω     91.00 178.00   0.50    3.50    --  123.25  45.00-180.00  174
 20  ω     91.00 178.00   0.50    3.50    --  123.25  45.00  30.00  174
 21  ω     91.00 178.00   0.50    3.50    --  123.25  45.00  30.00  174
 22  ω     47.00 105.00   0.50    3.50    --  123.25 -77.00  90.00  116
 23  ω     63.00 146.00   0.50    3.50    --  123.25 178.00 -60.00  166
 24  ω     45.00 108.00   0.50    3.50    --  123.25-111.00 -60.00  126
 25  ω     47.00 105.00   0.50    3.50    --  123.25 -77.00-150.00  116
 26  ω     43.00 101.00   0.50    3.50    --  123.25 -95.00 -60.00  116
 27  ω     45.00 102.00   0.50    3.50    --  123.25-111.00  90.00  114
 28  ω     48.00  94.00   0.50    3.50    --  123.25 -77.00-180.00   92
 29  ω    107.00 149.00   0.50    3.50    --  123.25 111.00-180.00   84
 30  ω     54.00  80.00   0.50    3.50    --  123.25   6.00 -55.80   52
 31  ω     49.00  74.00   0.50    3.50    --  123.25-111.00-180.00   50
 32  ω     77.00 108.00   0.50    3.50    --  123.25-111.00-180.00   62
 33  ω     42.00  67.00   0.50    3.50    --  123.25 -95.00  30.00   50
 34  ω     80.00 105.00   0.50    3.50    --  123.25 -95.00  30.00   50
 35  ω     55.00 101.00   0.50    3.50    --  123.25-111.00 120.00   92
 36  ω     56.00  99.00   0.50    3.50    --  123.25 -77.00-120.00   86
 37  ω     98.00 133.00   0.50    3.50    --  123.25  30.00-180.00   70
 38  ω    142.00 168.00   0.50    3.50    --  123.25  61.00  90.00   52
 39  ω     63.00  94.00   0.50    3.50    --  123.25 178.00 -60.00   62
 40  ω     45.00 108.00   0.50    3.50    --  123.25-111.00  30.00  126
 41  ω    103.00 149.00   0.50    3.50    --  123.25  45.00  90.00   92
 42  ω     62.00  88.00   0.50    3.50    --  123.25 -95.00 -90.00   52
 43  ω     93.00 119.00   0.50    3.50    --  123.25  61.00  90.00   52
 44  ω     80.00 133.00   0.50    3.50    --  123.25  30.00 -90.00  106
 45  ω    137.00 168.00   0.50    3.50    --  123.25  30.00 -90.00   62
 46  ω     98.00 123.00   0.50    3.50    --  123.25  61.00 120.00   50
 47  ω    139.00 164.00   0.50    3.50    --  123.25  61.00 120.00   50
 48  ω     58.00 105.00   0.50    3.50    --  123.25 -77.00 150.00   94
 49  ω     68.00  94.00   0.50    3.50    --  123.25 178.00 120.00   52
 50  ω    121.00 146.00   0.50    3.50    --  123.25 178.00 120.00   50
 51  ω     95.00 120.00   0.50    3.50    --  123.25  77.00-150.00   50
 52  ω    134.00 160.00   0.50    3.50    --  123.25  77.00-150.00   52
 53  ω     47.00  73.00   0.50    3.50    --  123.25-111.00  60.00   52
 54  ω     88.00 139.00   0.50    3.50    --  123.25 -81.00 -74.35  102
 55  ω    140.00 178.00   0.50    3.50    --  123.25  30.00-180.00   76
 56  ω     55.00 101.00   0.50    3.50    --  123.25 -77.00 120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0448928000
_diffrn_orient_matrix_UB_12      0.0073653000
_diffrn_orient_matrix_UB_13      0.0313945000
_diffrn_orient_matrix_UB_21      -0.0154057000
_diffrn_orient_matrix_UB_22      0.0574492000
_diffrn_orient_matrix_UB_23      0.0673501000
_diffrn_orient_matrix_UB_31      -0.0025142000
_diffrn_orient_matrix_UB_32      -0.2213775000
_diffrn_orient_matrix_UB_33      0.0185192000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8596
_reflns_number_total             9133
_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       'CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.117a 64-bit (release 26-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.014
_refine_diff_density_min         -1.142
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         9133
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1027P)²+3.9549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1308
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4825(11)
 0.5175(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
3. Restrained distances
 N5A-C5A \\sim N5B-C5B
 with sigma of 0.003
 C5A-C6A \\sim C5B-C6B
 with sigma of 0.003
 C7A-C6A \\sim C7B-C6B
 with sigma of 0.003
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.003
 C8A-C9A \\sim C8B-C9B
 with sigma of 0.003
 N5A-C9A \\sim N5B-C9B
 with sigma of 0.003
 N5A-C6A \\sim N5B-C6B
 with sigma of 0.003
 C5A-C7A \\sim C5B-C7B
 with sigma of 0.003
 C6A-C8A \\sim C6B-C8B
 with sigma of 0.003
 C7A-C9A \\sim C7B-C9B
 with sigma of 0.003
 C8A-N5A \\sim C8B-N5B
 with sigma of 0.003
 C3-N5A \\sim C3-N5B
 with sigma of 0.003
4. Uiso/Uaniso restraints and constraints
Uanis(C5A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C8A) \\sim Ueq: with sigma of
0.003 and sigma for terminal atoms of 0.006
Uanis(N5A) = Uanis(N5B)
Uanis(C5A) = Uanis(C5B)
Uanis(C6A) = Uanis(C6B)
Uanis(C7A) = Uanis(C7B)
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
5. Others
 Sof(N5B)=Sof(C5B)=Sof(H5C)=Sof(H5D)=Sof(C6B)=Sof(H6C)=Sof(H6D)=Sof(C7B)=
 Sof(H7C)=Sof(H7D)=Sof(C8B)=Sof(H8C)=Sof(H8D)=Sof(C9B)=Sof(H9C)=Sof(H9D)=1-
 FVAR(1)
 Sof(N5A)=Sof(C5A)=Sof(H5A)=Sof(H5B)=Sof(C6A)=Sof(H6A)=Sof(H6B)=Sof(C7A)=
 Sof(H7A)=Sof(H7B)=Sof(C8A)=Sof(H8A)=Sof(H8B)=Sof(C9A)=Sof(H9A)=Sof(H9B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C5A(H5A,H5B), C6A(H6A,H6B), C7A(H7A,H7B), C8A(H8A,H8B), C9A(H9A,H9B), C5B(H5C,
 H5D), C6B(H6C,H6D), C7B(H7C,H7D), C8B(H8C,H8D), C9B(H9C,H9D), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.63814(2) 0.22728(5) 0.57124(2) 0.02465(13) Uani 1 1 d . . . . .
Br2 Br 0.73771(2) 0.72292(6) 0.29504(2) 0.02918(14) Uani 1 1 d . . . . .
Se1 Se 0.74190(2) 0.23803(5) 0.40540(2) 0.01748(13) Uani 1 1 d . . . . .
Se2 Se 0.69673(2) 0.73970(5) 0.52730(2) 0.01852(13) Uani 1 1 d . . . . .
N1 N 0.70862(9) 0.2358(4) 0.47161(14) 0.0178(5) Uani 1 1 d . . . . .
N2 N 0.59756(8) 0.1771(4) 0.44683(13) 0.0233(5) Uani 1 1 d . . . . .
N3 N 0.59167(8) 0.1577(4) 0.37916(13) 0.0239(5) Uani 1 1 d . . . . .
N4 N 0.70020(8) 0.2082(4) 0.34201(13) 0.0186(5) Uani 1 1 d . . . . .
N6 N 0.71704(9) 0.7352(4) 0.44742(15) 0.0212(6) Uani 1 1 d . . . . .
N7 N 0.65401(9) 0.6787(4) 0.29146(13) 0.0240(5) Uani 1 1 d . . . . .
N8 N 0.61554(8) 0.6591(4) 0.31311(12) 0.0232(5) Uani 1 1 d . . . . .
N9 N 0.64442(8) 0.7101(4) 0.49273(13) 0.0186(5) Uani 1 1 d . . . . .
N10 N 0.57037(8) 0.6475(4) 0.39383(12) 0.0209(5) Uani 1 1 d . . . . .
C1 C 0.67050(9) 0.2124(4) 0.44371(15) 0.0169(5) Uani 1 1 d . . . . .
C2 C 0.63383(10) 0.2028(5) 0.47723(16) 0.0197(6) Uani 1 1 d . . . . .
C3 C 0.62338(9) 0.1651(4) 0.34112(15) 0.0193(5) Uani 1 1 d D . . . .
C4 C 0.66567(9) 0.1955(4) 0.37204(15) 0.0179(6) Uani 1 1 d . . . . .
N5A N 0.6135(3) 0.1366(18) 0.27583(17) 0.0246(7) Uani 0.548(14) 1 d D . P A 1
C5A C 0.5695(3) 0.1336(15) 0.2499(4) 0.0254(15) Uani 0.548(14) 1 d D U P A 1
H5A H 0.551886 0.161056 0.286391 0.030 Uiso 0.548(14) 1 calc R U P A 1
H5B H 0.562092 0.000838 0.231380 0.030 Uiso 0.548(14) 1 calc R U P A 1
C6A C 0.5620(2) 0.2914(14) 0.1956(5) 0.0241(15) Uani 0.548(14) 1 d D U P A 1
H6A H 0.533217 0.280907 0.175356 0.029 Uiso 0.548(14) 1 calc R U P A 1
H6B H 0.565623 0.424857 0.215887 0.029 Uiso 0.548(14) 1 calc R U P A 1
C7A C 0.5915(3) 0.268(2) 0.1416(4) 0.0271(12) Uani 0.548(14) 1 d D . P A 1
H7A H 0.587262 0.378791 0.109377 0.032 Uiso 0.548(14) 1 calc R U P A 1
H7B H 0.585678 0.142053 0.117474 0.032 Uiso 0.548(14) 1 calc R U P A 1
C8A C 0.6360(3) 0.2692(15) 0.1726(4) 0.0215(14) Uani 0.548(14) 1 d D U P A 1
H8A H 0.654795 0.245455 0.137437 0.026 Uiso 0.548(14) 1 calc R U P A 1
H8B H 0.642600 0.401286 0.192294 0.026 Uiso 0.548(14) 1 calc R U P A 1
C9A C 0.6432(3) 0.1111(16) 0.2259(5) 0.0236(19) Uani 0.548(14) 1 d D . P A 1
H9A H 0.639832 -0.022346 0.205541 0.028 Uiso 0.548(14) 1 calc R U P A 1
H9B H 0.671671 0.121909 0.247448 0.028 Uiso 0.548(14) 1 calc R U P A 1
N5B N 0.6160(3) 0.149(2) 0.27481(19) 0.0246(7) Uani 0.452(14) 1 d D . P A 2
C5B C 0.5757(3) 0.0785(16) 0.2432(6) 0.0254(15) Uani 0.452(14) 1 d D . P A 2
H5C H 0.556488 0.053729 0.277657 0.030 Uiso 0.452(14) 1 calc R U P A 2
H5D H 0.579451 -0.047395 0.219178 0.030 Uiso 0.452(14) 1 calc R U P A 2
C6B C 0.5577(3) 0.2371(18) 0.1946(6) 0.0241(15) Uani 0.452(14) 1 d D . P A 2
H6C H 0.530927 0.190099 0.172969 0.029 Uiso 0.452(14) 1 calc R U P A 2
H6D H 0.552535 0.359925 0.219481 0.029 Uiso 0.452(14) 1 calc R U P A 2
C7B C 0.5866(4) 0.284(2) 0.1414(5) 0.0271(12) Uani 0.452(14) 1 d D . P A 2
H7C H 0.576235 0.400742 0.115299 0.032 Uiso 0.452(14) 1 calc R U P A 2
H7D H 0.587523 0.169593 0.110680 0.032 Uiso 0.452(14) 1 calc R U P A 2
C8B C 0.6299(3) 0.3263(16) 0.1738(6) 0.0215(14) Uani 0.452(14) 1 d D . P A 2
H8C H 0.649328 0.336154 0.138876 0.026 Uiso 0.452(14) 1 calc R U P A 2
H8D H 0.629946 0.455545 0.197187 0.026 Uiso 0.452(14) 1 calc R U P A 2
C9B C 0.6445(4) 0.165(2) 0.2228(6) 0.0236(19) Uani 0.452(14) 1 d D . P A 2
H9C H 0.645918 0.036579 0.199291 0.028 Uiso 0.452(14) 1 calc R U P A 2
H9D H 0.672565 0.197375 0.243268 0.028 Uiso 0.452(14) 1 calc R U P A 2
C10 C 0.68529(10) 0.7118(4) 0.40259(16) 0.0190(6) Uani 1 1 d . . . . .
C11 C 0.68648(11) 0.7014(5) 0.33228(17) 0.0231(6) Uani 1 1 d . . . . .
C12 C 0.60938(9) 0.6671(4) 0.37792(14) 0.0183(5) Uani 1 1 d . . . . .
C13 C 0.64478(9) 0.6962(4) 0.42715(15) 0.0176(5) Uani 1 1 d . . . . .
C14 C 0.53661(10) 0.6204(6) 0.34151(15) 0.0294(7) Uani 1 1 d . . . . .
H14A H 0.525780 0.483285 0.343267 0.035 Uiso 1 1 calc R U . . .
H14B H 0.547032 0.640544 0.297442 0.035 Uiso 1 1 calc R U . . .
C15 C 0.50193(12) 0.7688(6) 0.35071(19) 0.0305(8) Uani 1 1 d . . . . .
H15A H 0.512030 0.905125 0.343548 0.037 Uiso 1 1 calc R U . . .
H15B H 0.478538 0.742751 0.316952 0.037 Uiso 1 1 calc R U . . .
C16 C 0.48690(11) 0.7547(5) 0.41985(19) 0.0266(7) Uani 1 1 d . . . . .
H16A H 0.466422 0.860642 0.425631 0.032 Uiso 1 1 calc R U . . .
H16B H 0.473353 0.624743 0.425226 0.032 Uiso 1 1 calc R U . . .
C17 C 0.52341(11) 0.7770(5) 0.47203(18) 0.0260(7) Uani 1 1 d . . . . .
H17A H 0.513993 0.757962 0.516859 0.031 Uiso 1 1 calc R U . . .
H17B H 0.534913 0.912712 0.469804 0.031 Uiso 1 1 calc R U . . .
C18 C 0.55693(9) 0.6250(5) 0.46073(14) 0.0235(6) Uani 1 1 d . . . . .
H18A H 0.580770 0.644171 0.494223 0.028 Uiso 1 1 calc R U . . .
H18B H 0.546053 0.489128 0.466088 0.028 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 1.898(3) . ?
Br2 C11 1.895(3) . ?
Se1 N1 1.795(3) . ?
Se1 N4 1.790(3) . ?
Se2 N6 1.798(3) . ?
Se2 N9 1.791(3) . ?
N1 C1 1.324(4) . ?
N2 N3 1.369(4) . ?
N2 C2 1.291(4) . ?
N3 C3 1.341(4) . ?
N4 C4 1.326(4) . ?
N6 C10 1.319(4) . ?
N7 N8 1.369(4) . ?
N7 C11 1.288(5) . ?
N8 C12 1.343(4) . ?
N9 C13 1.329(4) . ?
N10 C12 1.343(4) . ?
N10 C14 1.464(4) . ?
N10 C18 1.465(3) . ?
C1 C2 1.425(4) . ?
C1 C4 1.446(4) . ?
C3 C4 1.472(4) . ?
C3 N5A 1.342(4) . ?
C3 N5B 1.344(5) . ?
N5A C5A 1.480(5) . ?
N5A C9A 1.468(5) . ?
C5A H5A 0.9900 . ?
C5A H5B 0.9900 . ?
C5A C6A 1.529(6) . ?
C6A H6A 0.9900 . ?
C6A H6B 0.9900 . ?
C6A C7A 1.523(6) . ?
C7A H7A 0.9900 . ?
C7A H7B 0.9900 . ?
C7A C8A 1.525(6) . ?
C8A H8A 0.9900 . ?
C8A H8B 0.9900 . ?
C8A C9A 1.517(6) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
N5B C5B 1.481(5) . ?
N5B C9B 1.468(5) . ?
C5B H5C 0.9900 . ?
C5B H5D 0.9900 . ?
C5B C6B 1.530(6) . ?
C6B H6C 0.9900 . ?
C6B H6D 0.9900 . ?
C6B C7B 1.523(6) . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C7B C8B 1.524(6) . ?
C8B H8C 0.9900 . ?
C8B H8D 0.9900 . ?
C8B C9B 1.517(7) . ?
C9B H9C 0.9900 . ?
C9B H9D 0.9900 . ?
C10 C11 1.426(4) . ?
C10 C13 1.453(4) . ?
C12 C13 1.464(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.530(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.524(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.521(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.527(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
N4 Se1 N1 93.61(13) . . ?
N9 Se2 N6 93.53(13) . . ?
C1 N1 Se1 106.8(2) . . ?
C2 N2 N3 121.8(3) . . ?
C3 N3 N2 121.5(3) . . ?
C4 N4 Se1 107.4(2) . . ?
C10 N6 Se2 106.8(2) . . ?
C11 N7 N8 121.8(3) . . ?
C12 N8 N7 121.9(3) . . ?
C13 N9 Se2 107.6(2) . . ?
C12 N10 C14 120.2(2) . . ?
C12 N10 C18 126.7(2) . . ?
C14 N10 C18 112.7(2) . . ?
N1 C1 C2 126.5(3) . . ?
N1 C1 C4 116.6(3) . . ?
C2 C1 C4 116.9(3) . . ?
N2 C2 Br1 117.9(2) . . ?
N2 C2 C1 123.2(3) . . ?
C1 C2 Br1 118.8(2) . . ?
N3 C3 C4 120.0(3) . . ?
N3 C3 N5A 115.4(5) . . ?
N3 C3 N5B 119.3(5) . . ?
N5A C3 C4 124.6(5) . . ?
N5B C3 C4 120.7(5) . . ?
N4 C4 C1 115.6(3) . . ?
N4 C4 C3 127.7(3) . . ?
C1 C4 C3 116.6(3) . . ?
C3 N5A C5A 119.2(8) . . ?
C3 N5A C9A 125.3(7) . . ?
C9A N5A C5A 115.5(7) . . ?
N5A C5A H5A 109.8 . . ?
N5A C5A H5B 109.8 . . ?
N5A C5A C6A 109.2(4) . . ?
H5A C5A H5B 108.3 . . ?
C6A C5A H5A 109.8 . . ?
C6A C5A H5B 109.8 . . ?
C5A C6A H6A 109.2 . . ?
C5A C6A H6B 109.2 . . ?
H6A C6A H6B 107.9 . . ?
C7A C6A C5A 111.9(4) . . ?
C7A C6A H6A 109.2 . . ?
C7A C6A H6B 109.2 . . ?
C6A C7A H7A 109.7 . . ?
C6A C7A H7B 109.7 . . ?
C6A C7A C8A 110.0(4) . . ?
H7A C7A H7B 108.2 . . ?
C8A C7A H7A 109.7 . . ?
C8A C7A H7B 109.7 . . ?
C7A C8A H8A 109.3 . . ?
C7A C8A H8B 109.3 . . ?
H8A C8A H8B 108.0 . . ?
C9A C8A C7A 111.5(4) . . ?
C9A C8A H8A 109.3 . . ?
C9A C8A H8B 109.3 . . ?
N5A C9A C8A 109.7(4) . . ?
N5A C9A H9A 109.7 . . ?
N5A C9A H9B 109.7 . . ?
C8A C9A H9A 109.7 . . ?
C8A C9A H9B 109.7 . . ?
H9A C9A H9B 108.2 . . ?
C3 N5B C5B 121.8(9) . . ?
C3 N5B C9B 129.7(9) . . ?
C9B N5B C5B 108.0(9) . . ?
N5B C5B H5C 109.9 . . ?
N5B C5B H5D 109.9 . . ?
N5B C5B C6B 109.0(4) . . ?
H5C C5B H5D 108.3 . . ?
C6B C5B H5C 109.9 . . ?
C6B C5B H5D 109.9 . . ?
C5B C6B H6C 109.2 . . ?
C5B C6B H6D 109.2 . . ?
H6C C6B H6D 107.9 . . ?
C7B C6B C5B 111.8(4) . . ?
C7B C6B H6C 109.2 . . ?
C7B C6B H6D 109.2 . . ?
C6B C7B H7C 109.7 . . ?
C6B C7B H7D 109.7 . . ?
C6B C7B C8B 110.0(4) . . ?
H7C C7B H7D 108.2 . . ?
C8B C7B H7C 109.7 . . ?
C8B C7B H7D 109.7 . . ?
C7B C8B H8C 109.3 . . ?
C7B C8B H8D 109.3 . . ?
H8C C8B H8D 108.0 . . ?
C9B C8B C7B 111.6(4) . . ?
C9B C8B H8C 109.3 . . ?
C9B C8B H8D 109.3 . . ?
N5B C9B C8B 109.9(4) . . ?
N5B C9B H9C 109.7 . . ?
N5B C9B H9D 109.7 . . ?
C8B C9B H9C 109.7 . . ?
C8B C9B H9D 109.7 . . ?
H9C C9B H9D 108.2 . . ?
N6 C10 C11 126.8(3) . . ?
N6 C10 C13 116.9(3) . . ?
C11 C10 C13 116.3(3) . . ?
N7 C11 Br2 117.0(2) . . ?
N7 C11 C10 123.3(3) . . ?
C10 C11 Br2 119.7(3) . . ?
N8 C12 N10 117.2(3) . . ?
N8 C12 C13 119.3(3) . . ?
N10 C12 C13 123.5(3) . . ?
N9 C13 C10 115.2(3) . . ?
N9 C13 C12 127.5(3) . . ?
C10 C13 C12 117.3(3) . . ?
N10 C14 H14A 109.6 . . ?
N10 C14 H14B 109.6 . . ?
N10 C14 C15 110.1(3) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 111.8(3) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 C15 109.5(3) . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 C18 110.7(3) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
N10 C18 C17 110.2(3) . . ?
N10 C18 H18A 109.6 . . ?
N10 C18 H18B 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?

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 -179.7(3) . . . . ?
Se1 N1 C1 C4 0.1(3) . . . . ?
Se1 N4 C4 C1 1.2(3) . . . . ?
Se1 N4 C4 C3 -178.4(3) . . . . ?
Se2 N6 C10 C11 179.5(3) . . . . ?
Se2 N6 C10 C13 -0.1(3) . . . . ?
Se2 N9 C13 C10 -1.1(3) . . . . ?
Se2 N9 C13 C12 178.8(3) . . . . ?
N1 Se1 N4 C4 -1.0(2) . . . . ?
N1 C1 C2 Br1 0.5(4) . . . . ?
N1 C1 C2 N2 -179.1(3) . . . . ?
N1 C1 C4 N4 -0.9(4) . . . . ?
N1 C1 C4 C3 178.7(3) . . . . ?
N2 N3 C3 C4 -0.2(4) . . . . ?
N2 N3 C3 N5A 177.6(6) . . . . ?
N2 N3 C3 N5B -178.9(8) . . . . ?
N3 N2 C2 Br1 -179.9(2) . . . . ?
N3 N2 C2 C1 -0.3(5) . . . . ?
N3 C3 C4 N4 -179.4(3) . . . . ?
N3 C3 C4 C1 1.1(4) . . . . ?
N3 C3 N5A C5A 10.1(11) . . . . ?
N3 C3 N5A C9A -171.2(7) . . . . ?
N3 C3 N5B C5B -13.8(14) . . . . ?
N3 C3 N5B C9B 175.5(9) . . . . ?
N4 Se1 N1 C1 0.5(2) . . . . ?
N6 Se2 N9 C13 0.9(2) . . . . ?
N6 C10 C11 Br2 -0.2(5) . . . . ?
N6 C10 C11 N7 -179.8(3) . . . . ?
N6 C10 C13 N9 0.8(4) . . . . ?
N6 C10 C13 C12 -179.1(3) . . . . ?
N7 N8 C12 N10 179.6(3) . . . . ?
N7 N8 C12 C13 -0.4(4) . . . . ?
N8 N7 C11 Br2 179.2(2) . . . . ?
N8 N7 C11 C10 -1.2(5) . . . . ?
N8 C12 C13 N9 179.1(3) . . . . ?
N8 C12 C13 C10 -1.0(4) . . . . ?
N9 Se2 N6 C10 -0.4(2) . . . . ?
N10 C12 C13 N9 -0.9(5) . . . . ?
N10 C12 C13 C10 179.0(3) . . . . ?
N10 C14 C15 C16 -55.0(4) . . . . ?
C2 N2 N3 C3 -0.2(5) . . . . ?
C2 C1 C4 N4 178.9(3) . . . . ?
C2 C1 C4 C3 -1.4(4) . . . . ?
C3 N5A C5A C6A 123.3(9) . . . . ?
C3 N5A C9A C8A -122.2(9) . . . . ?
C3 N5B C5B C6B 122.7(11) . . . . ?
C3 N5B C9B C8B -122.8(12) . . . . ?
C4 C1 C2 Br1 -179.3(2) . . . . ?
C4 C1 C2 N2 1.1(5) . . . . ?
C4 C3 N5A C5A -172.2(6) . . . . ?
C4 C3 N5A C9A 6.5(13) . . . . ?
C4 C3 N5B C5B 167.5(8) . . . . ?
C4 C3 N5B C9B -3.1(16) . . . . ?
N5A C3 C4 N4 3.0(8) . . . . ?
N5A C3 C4 C1 -176.6(7) . . . . ?
N5A C5A C6A C7A 53.6(7) . . . . ?
C5A N5A C9A C8A 56.5(10) . . . . ?
C5A C6A C7A C8A -54.9(8) . . . . ?
C6A C7A C8A C9A 55.4(8) . . . . ?
C7A C8A C9A N5A -55.0(7) . . . . ?
C9A N5A C5A C6A -55.6(10) . . . . ?
N5B C3 C4 N4 -0.7(9) . . . . ?
N5B C3 C4 C1 179.7(8) . . . . ?
N5B C5B C6B C7B 58.3(8) . . . . ?
C5B N5B C9B C8B 65.6(12) . . . . ?
C5B C6B C7B C8B -50.5(9) . . . . ?
C6B C7B C8B C9B 50.4(9) . . . . ?
C7B C8B C9B N5B -58.9(8) . . . . ?
C9B N5B C5B C6B -64.9(11) . . . . ?
C11 N7 N8 C12 1.6(5) . . . . ?
C11 C10 C13 N9 -178.8(3) . . . . ?
C11 C10 C13 C12 1.3(4) . . . . ?
C12 N10 C14 C15 -129.3(3) . . . . ?
C12 N10 C18 C17 128.3(3) . . . . ?
C13 C10 C11 Br2 179.4(2) . . . . ?
C13 C10 C11 N7 -0.3(5) . . . . ?
C14 N10 C12 N8 -0.5(4) . . . . ?
C14 N10 C12 C13 179.5(3) . . . . ?
C14 N10 C18 C17 -59.4(4) . . . . ?
C14 C15 C16 C17 54.1(4) . . . . ?
C15 C16 C17 C18 -55.0(4) . . . . ?
C16 C17 C18 N10 57.6(4) . . . . ?
C18 N10 C12 N8 171.3(3) . . . . ?
C18 N10 C12 C13 -8.7(5) . . . . ?
C18 N10 C14 C15 57.8(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 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.451
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4825(11) 23217 6792 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5175(11) 23135 6792 nmt 0.4840 0.0006 1.4829 -0.0001 -0.9998 -0.0001 0.5175
-0.0005 -0.4824

_twin_special_details            
;
Component 2 rotated by 179.9957° 
around [0.94 -0.00 0.33] (reciprocal) or [0.71 0.00 0.71] (direct)
;
