# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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. 
# 
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data_1-Cl_Et4N
_database_code_depnum_ccdc_archive 'CCDC 2168136'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Radiush'
;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-22
_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            
;
tetraethilammonium 1-chloro-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_name_systematic        
;
tetraethilammonium 1-chloro-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_formula_moiety         'C6 N6 Se, Cl, C4 H8 O, C8 H20 N'
_chemical_formula_sum            'C18 H28 Cl N7 O Se'
_chemical_formula_weight         472.88
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0780(3)
_cell_length_b                   15.0011(8)
_cell_length_c                   21.4924(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.892(2)
_cell_angle_gamma                90
_cell_volume                     2280.77(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.41
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.541
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0867 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.8518.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.142
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            50168
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.282
_diffrn_reflns_theta_min         2.332
_diffrn_ambient_temperature      200.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5405
_reflns_number_total             6518
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         6518
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.091
_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)+(0.0511P)²+1.0199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C15 \\sim C18 \\sim C17: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.01 within 2A
3. Others
 Fixed Sof: H16C(0.5) H16D(0.5) H16A(0.5) H16B(0.5) H17C(0.5) H17D(0.5)
 H17A(0.5) H17B(0.5) C19(0.5) H19A(0.5) H19B(0.5) C18(0.5) H18A(0.5) H18B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16C,H16D), C16(H16A,H16B), C17(H17C,H17D), C17(H17A,
 H17B), C19(H19A,H19B), C18(H18A,H18B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,
 H11B), C13(H13A,H13B)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.24553(2) 0.39072(2) 0.48051(2) 0.02719(7) Uani 1 1 d . . . . .
N1 N 0.2925(2) 0.50644(10) 0.46644(7) 0.0278(3) Uani 1 1 d . . . . .
N2 N 0.1696(2) 0.40688(10) 0.56041(7) 0.0291(3) Uani 1 1 d . . . . .
N3 N 0.2705(2) 0.63886(11) 0.52502(7) 0.0278(3) Uani 1 1 d . . . . .
N4 N 0.1417(2) 0.52879(10) 0.62841(7) 0.0256(3) Uani 1 1 d . . . . .
N5 N 0.2617(3) 0.83974(12) 0.60065(10) 0.0508(5) Uani 1 1 d . . . . .
N6 N 0.0961(2) 0.68396(11) 0.74095(8) 0.0373(4) Uani 1 1 d . . . . .
C1 C 0.2511(2) 0.54796(12) 0.51963(7) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.1853(2) 0.49329(11) 0.57110(8) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.2285(2) 0.67002(11) 0.58020(8) 0.0269(3) Uani 1 1 d . . . . .
C4 C 0.1649(2) 0.61477(11) 0.63203(8) 0.0260(3) Uani 1 1 d . . . . .
C5 C 0.2482(3) 0.76537(13) 0.59063(9) 0.0353(4) Uani 1 1 d . . . . .
C6 C 0.1258(3) 0.65494(12) 0.69270(9) 0.0292(3) Uani 1 1 d . . . . .
Cl1 Cl 0.38615(7) 0.35112(3) 0.35124(2) 0.03296(11) Uani 1 1 d . . . . .
O1 O 0.1072(3) 0.21573(14) 0.49536(10) 0.0695(5) Uani 1 1 d . . . . .
C15 C 0.0387(7) 0.1818(3) 0.55279(17) 0.0921(12) Uani 1 1 d . U . . .
H15A H 0.009506 0.230943 0.581720 0.111 Uiso 1 1 calc R U . . .
H15B H -0.076016 0.145053 0.545516 0.111 Uiso 1 1 calc R U . . .
C16 C 0.2400(6) 0.1542(3) 0.47026(19) 0.0874(11) Uani 1 1 d . U . . .
H16C H 0.186276 0.127359 0.431490 0.105 Uiso 0.5 1 calc R U P A 2
H16D H 0.357737 0.185919 0.460156 0.105 Uiso 0.5 1 calc R U P A 2
H16A H 0.317046 0.181781 0.437818 0.105 Uiso 0.5 1 calc R U P B 1
H16B H 0.177838 0.099670 0.453602 0.105 Uiso 0.5 1 calc R U P B 1
C17 C 0.1890(10) 0.1304(5) 0.5760(3) 0.155(2) Uani 1 1 d . U . . .
H17C H 0.144239 0.082591 0.603600 0.186 Uiso 0.5 1 calc R U P C 2
H17D H 0.282701 0.167576 0.599302 0.186 Uiso 0.5 1 calc R U P C 2
H17A H 0.148784 0.067633 0.580701 0.186 Uiso 0.5 1 calc R U P D 1
H17B H 0.233064 0.153003 0.617225 0.186 Uiso 0.5 1 calc R U P D 1
C19 C 0.3519(13) 0.1367(7) 0.5286(4) 0.093(3) Uani 0.5 1 d . . P E 1
H19A H 0.439767 0.186283 0.538937 0.112 Uiso 0.5 1 calc R U P E 1
H19B H 0.423727 0.080241 0.526373 0.112 Uiso 0.5 1 calc R U P E 1
C18 C 0.279(2) 0.0888(10) 0.5131(6) 0.141(3) Uani 0.5 1 d . U P E 2
H18A H 0.417060 0.079110 0.518776 0.170 Uiso 0.5 1 calc R U P E 2
H18B H 0.217537 0.031835 0.501079 0.170 Uiso 0.5 1 calc R U P E 2
N7 N 0.2806(2) 0.58912(10) 0.25751(7) 0.0256(3) Uani 1 1 d . . . . .
C7 C 0.3107(3) 0.58624(12) 0.32728(8) 0.0292(4) Uani 1 1 d . . . . .
H7A H 0.185975 0.584617 0.346796 0.035 Uiso 1 1 calc R U . . .
H7B H 0.378341 0.530562 0.338768 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4206(3) 0.66388(15) 0.35290(10) 0.0443(5) Uani 1 1 d . . . . .
H8A H 0.547460 0.663746 0.335925 0.066 Uiso 1 1 calc R U . . .
H8B H 0.430765 0.659357 0.398372 0.066 Uiso 1 1 calc R U . . .
H8C H 0.355744 0.719394 0.341176 0.066 Uiso 1 1 calc R U . . .
C9 C 0.1661(3) 0.50686(13) 0.24260(9) 0.0309(4) Uani 1 1 d . . . . .
H9A H 0.233314 0.454254 0.260199 0.037 Uiso 1 1 calc R U . . .
H9B H 0.043141 0.511444 0.263013 0.037 Uiso 1 1 calc R U . . .
C10 C 0.1306(3) 0.49255(17) 0.17403(10) 0.0452(5) Uani 1 1 d . . . . .
H10A H 0.251473 0.484609 0.153754 0.068 Uiso 1 1 calc R U . . .
H10B H 0.064720 0.544483 0.156138 0.068 Uiso 1 1 calc R U . . .
H10C H 0.052491 0.439228 0.167452 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1782(3) 0.67394(13) 0.23942(9) 0.0344(4) Uani 1 1 d . . . . .
H11A H 0.151701 0.673248 0.193902 0.041 Uiso 1 1 calc R U . . .
H11B H 0.262774 0.725111 0.248760 0.041 Uiso 1 1 calc R U . . .
C12 C -0.0107(3) 0.68875(16) 0.27275(12) 0.0482(5) Uani 1 1 d . . . . .
H12A H -0.066138 0.745806 0.259494 0.072 Uiso 1 1 calc R U . . .
H12B H 0.013526 0.689488 0.317907 0.072 Uiso 1 1 calc R U . . .
H12C H -0.098602 0.640302 0.261882 0.072 Uiso 1 1 calc R U . . .
C13 C 0.4678(2) 0.58993(13) 0.22106(9) 0.0315(4) Uani 1 1 d . . . . .
H13A H 0.435316 0.595659 0.176073 0.038 Uiso 1 1 calc R U . . .
H13B H 0.541562 0.643376 0.233695 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5906(3) 0.50935(15) 0.23053(11) 0.0416(5) Uani 1 1 d . . . . .
H14A H 0.702710 0.514860 0.205250 0.062 Uiso 1 1 calc R U . . .
H14B H 0.519617 0.455848 0.217957 0.062 Uiso 1 1 calc R U . . .
H14C H 0.629707 0.504651 0.274572 0.062 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 1.7951(15) . ?
Se1 N2 1.8323(16) . ?
N1 C1 1.343(2) . ?
N2 C2 1.321(2) . ?
N3 C1 1.375(2) . ?
N3 C3 1.318(2) . ?
N4 C2 1.386(2) . ?
N4 C4 1.302(2) . ?
N5 C5 1.140(3) . ?
N6 C6 1.150(2) . ?
C1 C2 1.465(2) . ?
C3 C4 1.471(2) . ?
C3 C5 1.454(3) . ?
C4 C6 1.471(2) . ?
O1 C15 1.434(4) . ?
O1 C16 1.436(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C17 1.393(7) . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C19 1.484(9) . ?
C16 C18 1.368(14) . ?
C17 H17C 0.9900 . ?
C17 H17D 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C19 1.566(11) . ?
C17 C18 1.636(14) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N7 C7 1.508(2) . ?
N7 C9 1.505(2) . ?
N7 C11 1.509(2) . ?
N7 C13 1.561(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.496(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.502(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.553(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.499(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 Se1 N2 95.27(7) . . ?
C1 N1 Se1 104.96(12) . . ?
C2 N2 Se1 105.50(12) . . ?
C3 N3 C1 113.75(15) . . ?
C4 N4 C2 113.73(15) . . ?
N1 C1 N3 120.52(15) . . ?
N1 C1 C2 117.84(16) . . ?
N3 C1 C2 121.64(14) . . ?
N2 C2 N4 120.79(15) . . ?
N2 C2 C1 116.42(15) . . ?
N4 C2 C1 122.79(15) . . ?
N3 C3 C4 124.44(16) . . ?
N3 C3 C5 117.66(16) . . ?
C5 C3 C4 117.89(16) . . ?
N4 C4 C3 123.64(16) . . ?
N4 C4 C6 115.57(16) . . ?
C3 C4 C6 120.78(15) . . ?
N5 C5 C3 177.9(2) . . ?
N6 C6 C4 178.0(2) . . ?
C15 O1 C16 109.9(3) . . ?
O1 C15 H15A 111.1 . . ?
O1 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C17 C15 O1 103.2(4) . . ?
C17 C15 H15A 111.1 . . ?
C17 C15 H15B 111.1 . . ?
O1 C16 H16C 109.8 . . ?
O1 C16 H16D 109.8 . . ?
O1 C16 H16A 112.2 . . ?
O1 C16 H16B 112.2 . . ?
O1 C16 C19 97.7(4) . . ?
H16C C16 H16D 108.3 . . ?
H16A C16 H16B 109.8 . . ?
C19 C16 H16A 112.2 . . ?
C19 C16 H16B 112.2 . . ?
C18 C16 O1 109.2(6) . . ?
C18 C16 H16C 109.8 . . ?
C18 C16 H16D 109.8 . . ?
C15 C17 H17C 111.1 . . ?
C15 C17 H17D 111.1 . . ?
C15 C17 H17A 110.2 . . ?
C15 C17 H17B 110.2 . . ?
C15 C17 C19 107.7(5) . . ?
C15 C17 C18 103.3(6) . . ?
H17C C17 H17D 109.1 . . ?
H17A C17 H17B 108.5 . . ?
C19 C17 H17A 110.2 . . ?
C19 C17 H17B 110.2 . . ?
C18 C17 H17C 111.1 . . ?
C18 C17 H17D 111.1 . . ?
C16 C19 C17 100.2(6) . . ?
C16 C19 H19A 111.7 . . ?
C16 C19 H19B 111.7 . . ?
C17 C19 H19A 111.7 . . ?
C17 C19 H19B 111.7 . . ?
H19A C19 H19B 109.5 . . ?
C16 C18 C17 101.9(9) . . ?
C16 C18 H18A 111.4 . . ?
C16 C18 H18B 111.4 . . ?
C17 C18 H18A 111.4 . . ?
C17 C18 H18B 111.4 . . ?
H18A C18 H18B 109.3 . . ?
C7 N7 C11 109.34(15) . . ?
C7 N7 C13 113.88(13) . . ?
C9 N7 C7 104.22(13) . . ?
C9 N7 C11 112.70(14) . . ?
C9 N7 C13 111.06(14) . . ?
C11 N7 C13 105.81(13) . . ?
N7 C7 H7A 108.9 . . ?
N7 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 N7 113.48(15) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N7 C9 H9A 108.9 . . ?
N7 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 N7 113.42(15) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 H11A 108.6 . . ?
N7 C11 H11B 108.6 . . ?
N7 C11 C12 114.53(16) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N7 C13 H13A 108.5 . . ?
N7 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 N7 115.05(15) . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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 N3 -179.66(12) . . . . ?
Se1 N1 C1 C2 0.34(17) . . . . ?
Se1 N2 C2 N4 -178.86(12) . . . . ?
Se1 N2 C2 C1 0.89(18) . . . . ?
N1 Se1 N2 C2 -0.60(13) . . . . ?
N1 C1 C2 N2 -0.9(2) . . . . ?
N1 C1 C2 N4 178.85(15) . . . . ?
N2 Se1 N1 C1 0.14(12) . . . . ?
N3 C1 C2 N2 179.11(15) . . . . ?
N3 C1 C2 N4 -1.1(2) . . . . ?
N3 C3 C4 N4 -0.7(3) . . . . ?
N3 C3 C4 C6 178.36(16) . . . . ?
C1 N3 C3 C4 -0.4(2) . . . . ?
C1 N3 C3 C5 178.89(15) . . . . ?
C2 N4 C4 C3 0.9(2) . . . . ?
C2 N4 C4 C6 -178.23(14) . . . . ?
C3 N3 C1 N1 -178.71(15) . . . . ?
C3 N3 C1 C2 1.3(2) . . . . ?
C4 N4 C2 N2 179.71(16) . . . . ?
C4 N4 C2 C1 0.0(2) . . . . ?
C5 C3 C4 N4 179.94(17) . . . . ?
C5 C3 C4 C6 -1.0(2) . . . . ?
O1 C15 C17 C19 0.4(7) . . . . ?
O1 C15 C17 C18 -34.6(8) . . . . ?
O1 C16 C19 C17 41.2(7) . . . . ?
O1 C16 C18 C17 -12.7(11) . . . . ?
C15 O1 C16 C19 -45.8(6) . . . . ?
C15 O1 C16 C18 -8.3(9) . . . . ?
C15 C17 C19 C16 -27.3(8) . . . . ?
C15 C17 C18 C16 30.4(12) . . . . ?
C16 O1 C15 C17 28.9(5) . . . . ?
C7 N7 C9 C10 -175.91(17) . . . . ?
C7 N7 C11 C12 -54.7(2) . . . . ?
C7 N7 C13 C14 61.8(2) . . . . ?
C9 N7 C7 C8 -179.08(17) . . . . ?
C9 N7 C11 C12 60.7(2) . . . . ?
C9 N7 C13 C14 -55.5(2) . . . . ?
C11 N7 C7 C8 -58.4(2) . . . . ?
C11 N7 C9 C10 65.6(2) . . . . ?
C11 N7 C13 C14 -178.11(17) . . . . ?
C13 N7 C7 C8 59.7(2) . . . . ?
C13 N7 C9 C10 -52.9(2) . . . . ?
C13 N7 C11 C12 -177.71(17) . . . . ?

####################################################################### 
# 
# 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-I_Et4N
_database_code_depnum_ccdc_archive 'CCDC 2168138'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Radiush'
;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
;
tetraethilammonium 1-iodo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_name_systematic        
;
tetraethilammonium 1-iodo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_formula_moiety         '2(I), 2(C6 N6 Se), 2(C8 H20 N), C4 H10 O'
_chemical_formula_sum            'C32 H50 I2 N14 O Se2'
_chemical_formula_weight         1058.58
_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'
I I -0.4742 1.8119 '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           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                   16.8201(8)
_cell_length_b                   20.0393(11)
_cell_length_c                   13.7957(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.564(2)
_cell_angle_gamma                90
_cell_volume                     4294.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.586
_shelx_estimated_absorpt_T_max   0.740
_shelx_estimated_absorpt_T_min   0.186
_exptl_absorpt_coefficient_mu    3.203
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.793
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23349
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         2.033
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3312
_reflns_number_total             4210
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.252
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.074
_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)+(0.0545P)²+22.2150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C9(H9A,H9B), C17(H17A,H17B)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C16(H16A,
 H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I001 I 0.500000 0.67537(2) 0.250000 0.04323(15) Uani 1 2 d S T P . .
I002 I 1.000000 0.56274(2) 0.750000 0.04740(16) Uani 1 2 d S T P . .
Se1 Se 0.84926(3) 0.69107(2) 0.67360(4) 0.03968(15) Uani 1 1 d . . . . .
N1 N 0.2173(2) 0.53325(18) 0.1420(3) 0.0354(8) Uani 1 1 d . . . . .
N2 N 0.6144(3) 0.74998(19) 0.5472(3) 0.0397(9) Uani 1 1 d . . . . .
N3 N 0.6269(3) 0.60706(19) 0.5730(3) 0.0421(9) Uani 1 1 d . . . . .
N4 N 0.7765(3) 0.62147(19) 0.6440(3) 0.0413(9) Uani 1 1 d . . . . .
N5 N 0.4149(3) 0.5688(3) 0.4877(5) 0.0758(16) Uani 1 1 d . . . . .
N6 N 0.3977(3) 0.7664(3) 0.4405(4) 0.0684(14) Uani 1 1 d . . . . .
O7 O 0.500000 0.7145(3) 0.750000 0.0802(19) Uani 1 2 d S T P . .
C1 C 0.0649(4) 0.5820(3) 0.0703(5) 0.0611(15) Uani 1 1 d . . . . .
H1A H 0.043601 0.537537 0.069666 0.092 Uiso 1 1 calc R U . . .
H1B H 0.025774 0.606460 0.011458 0.092 Uiso 1 1 calc R U . . .
H1C H 0.069847 0.603945 0.134240 0.092 Uiso 1 1 calc R U . . .
C2 C 0.1528(3) 0.5792(2) 0.0632(4) 0.0446(11) Uani 1 1 d . . . . .
H2A H 0.145246 0.564737 -0.006896 0.054 Uiso 1 1 calc R U . . .
H2B H 0.176620 0.623891 0.072840 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1888(3) 0.4605(2) 0.1212(4) 0.0455(11) Uani 1 1 d . . . . .
H3A H 0.230009 0.433012 0.174988 0.055 Uiso 1 1 calc R U . . .
H3B H 0.133699 0.455826 0.127860 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1801(4) 0.4341(3) 0.0154(5) 0.0633(16) Uani 1 1 d . . . . .
H4A H 0.139097 0.460613 -0.038785 0.095 Uiso 1 1 calc R U . . .
H4B H 0.160636 0.388600 0.008479 0.095 Uiso 1 1 calc R U . . .
H4C H 0.234898 0.436086 0.009100 0.095 Uiso 1 1 calc R U . . .
C5 C 0.2491(4) 0.6208(3) 0.2855(4) 0.0582(14) Uani 1 1 d . . . . .
H5A H 0.304137 0.630903 0.283077 0.087 Uiso 1 1 calc R U . . .
H5B H 0.251815 0.627266 0.355628 0.087 Uiso 1 1 calc R U . . .
H5C H 0.206235 0.649899 0.238395 0.087 Uiso 1 1 calc R U . . .
C6 C 0.2256(4) 0.5487(2) 0.2527(4) 0.0459(11) Uani 1 1 d . . . . .
H6A H 0.269332 0.519883 0.300855 0.055 Uiso 1 1 calc R U . . .
H6B H 0.171475 0.538462 0.259048 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3025(3) 0.5443(3) 0.1297(4) 0.0490(12) Uani 1 1 d . . . . .
H9A H 0.318381 0.590860 0.143546 0.059 Uiso 1 1 calc R U . . .
H9B H 0.294064 0.535384 0.057237 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3773(4) 0.5016(3) 0.2005(6) 0.0674(17) Uani 1 1 d . . . . .
H8A H 0.390563 0.513292 0.272523 0.101 Uiso 1 1 calc R U . . .
H8B H 0.426856 0.509332 0.183624 0.101 Uiso 1 1 calc R U . . .
H8C H 0.361620 0.455314 0.190000 0.101 Uiso 1 1 calc R U . . .
N9 N 0.7652(3) 0.75230(19) 0.6240(3) 0.0418(9) Uani 1 1 d . . . . .
C10 C 0.6924(3) 0.7184(2) 0.5902(3) 0.0358(10) Uani 1 1 d . . . . .
C11 C 0.5474(3) 0.7107(2) 0.5178(4) 0.0399(10) Uani 1 1 d . . . . .
C12 C 0.5537(3) 0.6392(2) 0.5323(4) 0.0385(10) Uani 1 1 d . . . . .
C13 C 0.6983(3) 0.6474(2) 0.6016(3) 0.0363(10) Uani 1 1 d . . . . .
C14 C 0.4756(4) 0.5997(3) 0.5049(5) 0.0527(13) Uani 1 1 d . . . . .
C15 C 0.4632(3) 0.7410(3) 0.4728(4) 0.0491(12) Uani 1 1 d . . . . .
C16 C 0.3492(6) 0.7083(4) 0.6620(7) 0.094(2) Uani 1 1 d . . . . .
H16A H 0.360457 0.678849 0.613780 0.141 Uiso 1 1 calc R U . . .
H16B H 0.298321 0.733895 0.625023 0.141 Uiso 1 1 calc R U . . .
H16C H 0.340924 0.682540 0.715999 0.141 Uiso 1 1 calc R U . . .
C17 C 0.4233(5) 0.7539(3) 0.7099(5) 0.0723(18) Uani 1 1 d . . . . .
H17A H 0.426591 0.785086 0.657743 0.087 Uiso 1 1 calc R U . . .
H17B H 0.416626 0.779192 0.766270 0.087 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 N4 1.796(4) . ?
Se1 N9 1.797(4) . ?
N1 C2 1.517(6) . ?
N1 C3 1.527(6) . ?
N1 C6 1.511(6) . ?
N1 C9 1.523(6) . ?
N2 C10 1.370(6) . ?
N2 C11 1.304(6) . ?
N3 C12 1.309(6) . ?
N3 C13 1.374(6) . ?
N4 C13 1.324(6) . ?
N5 C14 1.137(7) . ?
N6 C15 1.139(7) . ?
O7 C17 1.430(7) 2_656 ?
O7 C17 1.430(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.519(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.506(7) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 C6 1.520(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.525(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N9 C10 1.319(6) . ?
C10 C13 1.431(6) . ?
C11 C12 1.446(7) . ?
C11 C15 1.442(7) . ?
C12 C14 1.454(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C17 1.482(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Se1 N9 94.36(18) . . ?
C2 N1 C3 110.9(4) . . ?
C2 N1 C9 106.1(4) . . ?
C6 N1 C2 111.3(4) . . ?
C6 N1 C3 106.7(3) . . ?
C6 N1 C9 110.9(4) . . ?
C9 N1 C3 111.0(4) . . ?
C11 N2 C10 115.2(4) . . ?
C12 N3 C13 114.1(4) . . ?
C13 N4 Se1 105.7(3) . . ?
C17 O7 C17 113.0(7) . 2_656 ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 115.0(4) . . ?
N1 C2 H2A 108.5 . . ?
N1 C2 H2B 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
N1 C3 H3A 108.5 . . ?
N1 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 N1 115.2(4) . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
N1 C6 C5 114.1(4) . . ?
N1 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N1 C9 H9A 108.4 . . ?
N1 C9 H9B 108.4 . . ?
N1 C9 C8 115.3(4) . . ?
H9A C9 H9B 107.5 . . ?
C8 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 N9 Se1 105.7(3) . . ?
N2 C10 C13 121.4(4) . . ?
N9 C10 N2 121.4(4) . . ?
N9 C10 C13 117.2(4) . . ?
N2 C11 C12 123.1(4) . . ?
N2 C11 C15 117.9(4) . . ?
C15 C11 C12 119.0(4) . . ?
N3 C12 C11 123.6(4) . . ?
N3 C12 C14 116.8(4) . . ?
C11 C12 C14 119.5(4) . . ?
N3 C13 C10 122.5(4) . . ?
N4 C13 N3 120.5(4) . . ?
N4 C13 C10 117.0(4) . . ?
N5 C14 C12 177.2(7) . . ?
N6 C15 C11 177.4(6) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
O7 C17 C16 108.1(6) . . ?
O7 C17 H17A 110.1 . . ?
O7 C17 H17B 110.1 . . ?
C16 C17 H17A 110.1 . . ?
C16 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?

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 N4 C13 N3 -177.7(3) . . . . ?
Se1 N4 C13 C10 0.6(5) . . . . ?
Se1 N9 C10 N2 179.8(3) . . . . ?
Se1 N9 C10 C13 0.5(5) . . . . ?
N2 C10 C13 N3 -1.8(7) . . . . ?
N2 C10 C13 N4 180.0(4) . . . . ?
N2 C11 C12 N3 -2.2(7) . . . . ?
N2 C11 C12 C14 175.1(5) . . . . ?
N4 Se1 N9 C10 -0.1(3) . . . . ?
C2 N1 C3 C4 61.0(6) . . . . ?
C2 N1 C6 C5 -55.7(6) . . . . ?
C2 N1 C9 C8 -178.8(5) . . . . ?
C3 N1 C2 C1 65.9(5) . . . . ?
C3 N1 C6 C5 -176.9(4) . . . . ?
C3 N1 C9 C8 -58.2(6) . . . . ?
C6 N1 C2 C1 -52.7(5) . . . . ?
C6 N1 C3 C4 -177.6(5) . . . . ?
C6 N1 C9 C8 60.2(6) . . . . ?
C9 N1 C2 C1 -173.5(4) . . . . ?
C9 N1 C3 C4 -56.7(6) . . . . ?
C9 N1 C6 C5 62.1(5) . . . . ?
N9 Se1 N4 C13 -0.2(3) . . . . ?
N9 C10 C13 N3 177.5(4) . . . . ?
N9 C10 C13 N4 -0.7(6) . . . . ?
C10 N2 C11 C12 2.1(7) . . . . ?
C10 N2 C11 C15 179.4(4) . . . . ?
C11 N2 C10 N9 -179.5(4) . . . . ?
C11 N2 C10 C13 -0.2(6) . . . . ?
C12 N3 C13 N4 179.9(4) . . . . ?
C12 N3 C13 C10 1.7(6) . . . . ?
C13 N3 C12 C11 0.2(7) . . . . ?
C13 N3 C12 C14 -177.2(4) . . . . ?
C15 C11 C12 N3 -179.5(5) . . . . ?
C15 C11 C12 C14 -2.2(7) . . . . ?
C17 O7 C17 C16 174.8(6) 2_656 . . . ?

####################################################################### 
# 
# 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-Br_Et4N
_database_code_depnum_ccdc_archive 'CCDC 2168137'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Radiush'
;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-22
_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            
;
tetraethilammonium 1-bromo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_name_systematic        
;
tetraethilammonium 1-bromo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_formula_moiety         'Br, C6 N6 Se, C2 H5 O0.5, C8 H20 N'
_chemical_formula_sum            'C16 H25 Br N7 O0.50 Se'
_chemical_formula_weight         482.30
_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           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                   16.5590(7)
_cell_length_b                   19.9679(9)
_cell_length_c                   13.5371(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.668(2)
_cell_angle_gamma                90
_cell_volume                     4130.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.62
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.314
_shelx_estimated_absorpt_T_min   0.152
_exptl_absorpt_coefficient_mu    3.770
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.5301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1068 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.6149.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37529
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.612
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3315
_reflns_number_total             4718
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4718
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.052
_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)+(0.0268P)²+4.1767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0731
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.000000 0.43341(2) 0.250000 0.05525(12) Uani 1 2 d S T P . .
Se1 Se 0.85908(2) 0.30987(2) 0.17915(2) 0.03927(8) Uani 1 1 d . . . . .
Br2 Br 1.000000 0.18012(2) 0.250000 0.04778(11) Uani 1 2 d S T P . .
N2 N 0.77380(13) 0.24835(10) 0.12812(16) 0.0407(5) Uani 1 1 d . . . . .
C6 C 0.69942(15) 0.28215(11) 0.09253(17) 0.0336(5) Uani 1 1 d . . . . .
N3 N 0.62022(13) 0.25076(9) 0.04802(16) 0.0385(5) Uani 1 1 d . . . . .
N4 N 0.63316(13) 0.39359(9) 0.07347(16) 0.0405(5) Uani 1 1 d . . . . .
C4 C 0.70559(15) 0.35361(11) 0.10373(17) 0.0339(5) Uani 1 1 d . . . . .
N1 N 0.78490(13) 0.37929(9) 0.14731(16) 0.0403(5) Uani 1 1 d . . . . .
O1 O 0.500000 0.29044(16) 0.250000 0.0835(10) Uani 1 2 d S T P . .
C1 C 0.55221(16) 0.29037(11) 0.01732(18) 0.0368(5) Uani 1 1 d . . . . .
C2 C 0.55875(15) 0.36171(11) 0.03156(19) 0.0375(5) Uani 1 1 d . . . . .
C3 C 0.47983(18) 0.40143(13) 0.0033(2) 0.0493(7) Uani 1 1 d . . . . .
N5 N 0.41773(17) 0.43178(13) -0.0145(2) 0.0737(8) Uani 1 1 d . . . . .
C5 C 0.46654(18) 0.25946(13) -0.0290(2) 0.0455(6) Uani 1 1 d . . . . .
N6 N 0.40006(17) 0.23432(13) -0.0610(2) 0.0641(7) Uani 1 1 d . . . . .
C7 C 0.6540(2) 0.29641(19) 0.3411(3) 0.0855(11) Uani 1 1 d . . . . .
H7A H 0.656128 0.328347 0.289187 0.128 Uiso 1 1 calc R U . . .
H7B H 0.706779 0.270386 0.366290 0.128 Uiso 1 1 calc R U . . .
H7C H 0.648317 0.319608 0.400252 0.128 Uiso 1 1 calc R U . . .
C8 C 0.5771(2) 0.25107(17) 0.2907(3) 0.0709(9) Uani 1 1 d . . . . .
H8A H 0.583741 0.225809 0.233104 0.085 Uiso 1 1 calc R U . . .
H8B H 0.573257 0.219657 0.343378 0.085 Uiso 1 1 calc R U . . .
C9 C 0.94141(19) 0.58156(16) 0.4265(3) 0.0674(9) Uani 1 1 d . . . . .
H9A H 0.959788 0.536658 0.420593 0.101 Uiso 1 1 calc R U . . .
H9B H 0.983791 0.602564 0.488709 0.101 Uiso 1 1 calc R U . . .
H9C H 0.936382 0.606527 0.363826 0.101 Uiso 1 1 calc R U . . .
C10 C 0.85389(17) 0.57985(12) 0.4367(2) 0.0484(7) Uani 1 1 d . . . . .
H10A H 0.831381 0.625220 0.429404 0.058 Uiso 1 1 calc R U . . .
H10B H 0.862880 0.564618 0.508204 0.058 Uiso 1 1 calc R U . . .
N7 N 0.78496(12) 0.53586(9) 0.35674(15) 0.0370(4) Uani 1 1 d . . . . .
C12 C 0.77551(18) 0.55149(12) 0.24363(19) 0.0461(6) Uani 1 1 d . . . . .
H12A H 0.730116 0.523101 0.194742 0.055 Uiso 1 1 calc R U . . .
H12B H 0.829927 0.540470 0.236167 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7531(2) 0.62373(13) 0.2114(2) 0.0596(8) Uani 1 1 d . . . . .
H13A H 0.698374 0.634819 0.216390 0.089 Uiso 1 1 calc R U . . .
H13B H 0.748323 0.629984 0.139034 0.089 Uiso 1 1 calc R U . . .
H13C H 0.798299 0.652261 0.258245 0.089 Uiso 1 1 calc R U . . .
C14 C 0.8186(2) 0.43568(14) 0.4840(2) 0.0601(8) Uani 1 1 d . . . . .
H14A H 0.862585 0.460426 0.539879 0.090 Uiso 1 1 calc R U . . .
H14B H 0.834747 0.389234 0.489387 0.090 Uiso 1 1 calc R U . . .
H14C H 0.763422 0.440330 0.491107 0.090 Uiso 1 1 calc R U . . .
C15 C 0.81102(17) 0.46248(11) 0.3765(2) 0.0439(6) Uani 1 1 d . . . . .
H15A H 0.768103 0.435886 0.320972 0.053 Uiso 1 1 calc R U . . .
H15B H 0.866858 0.456538 0.369901 0.053 Uiso 1 1 calc R U . . .
C16 C 0.70028(17) 0.54914(13) 0.3714(2) 0.0487(6) Uani 1 1 d . . . . .
H16A H 0.709872 0.540589 0.445584 0.058 Uiso 1 1 calc R U . . .
H16B H 0.686004 0.596234 0.357645 0.058 Uiso 1 1 calc R U . . .
C17 C 0.62265(19) 0.50865(17) 0.3016(3) 0.0702(9) Uani 1 1 d . . . . .
H17A H 0.613720 0.515027 0.227855 0.105 Uiso 1 1 calc R U . . .
H17B H 0.571491 0.522990 0.312834 0.105 Uiso 1 1 calc R U . . .
H17C H 0.633175 0.462092 0.319682 0.105 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 N2 1.797(2) . ?
Se1 N1 1.7912(19) . ?
N2 C6 1.322(3) . ?
C6 N3 1.366(3) . ?
C6 C4 1.434(3) . ?
N3 C1 1.306(3) . ?
N4 C4 1.366(3) . ?
N4 C2 1.306(3) . ?
C4 N1 1.319(3) . ?
O1 C8 1.417(3) . ?
O1 C8 1.417(3) 2_655 ?
C1 C2 1.436(3) . ?
C1 C5 1.450(4) . ?
C2 C3 1.448(4) . ?
C3 N5 1.137(3) . ?
C5 N6 1.133(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C8 1.496(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C10 1.508(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 N7 1.514(3) . ?
N7 C12 1.511(3) . ?
N7 C15 1.522(3) . ?
N7 C16 1.513(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.511(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C15 1.509(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.504(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 94.14(9) . . ?
C6 N2 Se1 105.96(15) . . ?
N2 C6 N3 121.9(2) . . ?
N2 C6 C4 116.8(2) . . ?
N3 C6 C4 121.3(2) . . ?
C1 N3 C6 115.20(19) . . ?
C2 N4 C4 114.69(19) . . ?
N4 C4 C6 122.1(2) . . ?
N1 C4 C6 116.9(2) . . ?
N1 C4 N4 121.0(2) . . ?
C4 N1 Se1 106.21(15) . . ?
C8 O1 C8 112.6(4) . 2_655 ?
N3 C1 C2 123.2(2) . . ?
N3 C1 C5 117.4(2) . . ?
C2 C1 C5 119.4(2) . . ?
N4 C2 C1 123.5(2) . . ?
N4 C2 C3 116.9(2) . . ?
C1 C2 C3 119.6(2) . . ?
N5 C3 C2 176.8(3) . . ?
N6 C5 C1 177.0(3) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
O1 C8 C7 108.8(3) . . ?
O1 C8 H8A 109.9 . . ?
O1 C8 H8B 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
C9 C10 N7 115.7(2) . . ?
H10A C10 H10B 107.4 . . ?
N7 C10 H10A 108.3 . . ?
N7 C10 H10B 108.3 . . ?
C10 N7 C15 110.38(18) . . ?
C12 N7 C10 111.08(19) . . ?
C12 N7 C15 106.80(18) . . ?
C12 N7 C16 110.93(19) . . ?
C16 N7 C10 106.62(19) . . ?
C16 N7 C15 111.10(19) . . ?
N7 C12 H12A 108.7 . . ?
N7 C12 H12B 108.7 . . ?
N7 C12 C13 114.1(2) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
N7 C15 H15A 108.5 . . ?
N7 C15 H15B 108.5 . . ?
C14 C15 N7 115.1(2) . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
N7 C16 H16A 108.3 . . ?
N7 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C17 C16 N7 115.8(2) . . ?
C17 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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 N2 C6 N3 -179.83(17) . . . . ?
Se1 N2 C6 C4 -0.4(2) . . . . ?
N2 Se1 N1 C4 0.41(17) . . . . ?
N2 C6 N3 C1 179.4(2) . . . . ?
N2 C6 C4 N4 -177.6(2) . . . . ?
N2 C6 C4 N1 0.8(3) . . . . ?
C6 N3 C1 C2 -1.8(3) . . . . ?
C6 N3 C1 C5 -179.1(2) . . . . ?
C6 C4 N1 Se1 -0.7(2) . . . . ?
N3 C6 C4 N4 1.8(3) . . . . ?
N3 C6 C4 N1 -179.8(2) . . . . ?
N3 C1 C2 N4 2.1(4) . . . . ?
N3 C1 C2 C3 -174.9(2) . . . . ?
N4 C4 N1 Se1 177.70(18) . . . . ?
C4 C6 N3 C1 0.0(3) . . . . ?
C4 N4 C2 C1 -0.3(3) . . . . ?
C4 N4 C2 C3 176.9(2) . . . . ?
N1 Se1 N2 C6 0.00(17) . . . . ?
C2 N4 C4 C6 -1.6(3) . . . . ?
C2 N4 C4 N1 -179.9(2) . . . . ?
C5 C1 C2 N4 179.4(2) . . . . ?
C5 C1 C2 C3 2.3(3) . . . . ?
C8 O1 C8 C7 -174.6(3) 2_655 . . . ?
C9 C10 N7 C12 -51.3(3) . . . . ?
C9 C10 N7 C15 66.9(3) . . . . ?
C9 C10 N7 C16 -172.3(2) . . . . ?
C10 N7 C12 C13 -57.3(3) . . . . ?
C10 N7 C15 C14 62.6(3) . . . . ?
C10 N7 C16 C17 -178.1(2) . . . . ?
C12 N7 C15 C14 -176.5(2) . . . . ?
C12 N7 C16 C17 60.8(3) . . . . ?
C15 N7 C12 C13 -177.7(2) . . . . ?
C15 N7 C16 C17 -57.8(3) . . . . ?
C16 N7 C12 C13 61.1(3) . . . . ?
C16 N7 C15 C14 -55.5(3) . . . . ?

####################################################################### 
# 
# 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-Cl_Ph4P
_database_code_depnum_ccdc_archive 'CCDC 2168141'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Radiush'
;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-22
_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            
;
tetraphenylphosphonium 1-chloro-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_name_systematic        
;
tetraphenylphosphonium 1-chloro-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_formula_moiety         'C6 N6 Se, Cl, C24 H20 P'
_chemical_formula_sum            'C30 H20 Cl N6 P Se'
_chemical_formula_weight         609.90
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9738(2)
_cell_length_b                   14.0802(6)
_cell_length_c                   14.7332(7)
_cell_angle_alpha                103.557(2)
_cell_angle_beta                 94.675(2)
_cell_angle_gamma                93.3900(10)
_cell_volume                     1397.12(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.374
_exptl_absorpt_coefficient_mu    1.528
_exptl_absorpt_correction_T_max  0.9011
_exptl_absorpt_correction_T_min  0.7467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0532 before and 0.0362 after correction.
The Ratio of minimum to maximum transmission is 0.8287.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26226
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.622
_diffrn_reflns_theta_min         2.301
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4843
_reflns_number_total             6573
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.8076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.1000
_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:
 C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.75154(4) 0.97726(2) 1.57729(2) 0.05116(10) Uani 1 1 d . . . . .
Cl00 Cl 0.82124(10) 1.18026(4) 1.69497(5) 0.05112(16) Uani 1 1 d . . . . .
P1 P 0.46016(8) 0.70115(4) 0.78095(4) 0.03526(13) Uani 1 1 d . . . . .
N1 N 0.7236(3) 0.84936(15) 1.51967(15) 0.0495(5) Uani 1 1 d . . . . .
N2 N 0.6963(3) 0.75703(15) 1.36413(15) 0.0463(5) Uani 1 1 d . . . . .
N3 N 0.7063(3) 0.94207(15) 1.31053(15) 0.0462(5) Uani 1 1 d . . . . .
N4 N 0.7417(3) 1.01824(15) 1.47138(15) 0.0494(5) Uani 1 1 d . . . . .
N5 N 0.6658(5) 0.8559(3) 1.0746(2) 0.0870(9) Uani 1 1 d . . . . .
N6 N 0.6853(5) 0.6068(2) 1.1461(2) 0.0892(9) Uani 1 1 d . . . . .
C1 C 0.7113(3) 0.84482(17) 1.42900(17) 0.0410(5) Uani 1 1 d . . . . .
C2 C 0.6883(3) 0.76487(18) 1.27776(18) 0.0460(6) Uani 1 1 d . . . . .
C3 C 0.6898(3) 0.85706(19) 1.25080(18) 0.0457(6) Uani 1 1 d . . . . .
C4 C 0.7201(3) 0.93709(17) 1.40217(18) 0.0425(5) Uani 1 1 d . . . . .
C5 C 0.6748(4) 0.8566(2) 1.1517(2) 0.0578(7) Uani 1 1 d . . . . .
C6 C 0.6838(4) 0.6751(2) 1.2046(2) 0.0596(7) Uani 1 1 d . . . . .
C7 C 0.8660(4) 0.9756(2) 0.8144(2) 0.0629(8) Uani 1 1 d . . . . .
H7 H 0.947603 1.031764 0.820012 0.075 Uiso 1 1 calc R U . . .
C8 C 0.7142(5) 0.9781(2) 0.8686(2) 0.0707(9) Uani 1 1 d . . . . .
H8 H 0.693263 1.036398 0.910263 0.085 Uiso 1 1 calc R U . . .
C9 C 0.5929(4) 0.89568(19) 0.86207(19) 0.0537(6) Uani 1 1 d . . . . .
H9 H 0.492808 0.897602 0.900301 0.064 Uiso 1 1 calc R U . . .
C10 C 0.6215(3) 0.80936(16) 0.79769(15) 0.0372(5) Uani 1 1 d . . . . .
C11 C 0.3266(3) 0.70768(16) 0.88116(15) 0.0385(5) Uani 1 1 d . . . . .
C12 C 0.3616(4) 0.6501(2) 0.94412(18) 0.0534(6) Uani 1 1 d . . . . .
H12 H 0.450995 0.603170 0.933646 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2611(5) 0.6634(3) 1.0232(2) 0.0709(9) Uani 1 1 d . . . . .
H13 H 0.283928 0.625149 1.065903 0.085 Uiso 1 1 calc R U . . .
C14 C 0.1289(5) 0.7320(3) 1.0391(2) 0.0721(9) Uani 1 1 d . . . . .
H14 H 0.064979 0.741225 1.093148 0.086 Uiso 1 1 calc R U . . .
C15 C 0.0343(4) 0.6689(2) 0.52211(19) 0.0574(7) Uani 1 1 d . . . . .
H15 H -0.052286 0.661129 0.468966 0.069 Uiso 1 1 calc R U . . .
C16 C 0.1882(5) 0.7378(2) 0.53831(19) 0.0593(7) Uani 1 1 d . . . . .
H16 H 0.205561 0.776721 0.496178 0.071 Uiso 1 1 calc R U . . .
C17 C 0.3173(4) 0.74957(18) 0.61678(17) 0.0488(6) Uani 1 1 d . . . . .
H17 H 0.421042 0.796773 0.627660 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2932(3) 0.69145(16) 0.67945(15) 0.0373(5) Uani 1 1 d . . . . .
C19 C 0.8971(4) 0.8903(2) 0.7522(2) 0.0528(6) Uani 1 1 d . . . . .
H19 H 1.000906 0.888485 0.716132 0.063 Uiso 1 1 calc R U . . .
C20 C 0.7749(4) 0.80732(18) 0.74284(19) 0.0471(6) Uani 1 1 d . . . . .
H20 H 0.795115 0.749837 0.699771 0.057 Uiso 1 1 calc R U . . .
C21 C 0.0907(4) 0.7873(2) 0.9754(2) 0.0614(8) Uani 1 1 d . . . . .
H21 H -0.001917 0.832568 0.985315 0.074 Uiso 1 1 calc R U . . .
C22 C 0.1893(4) 0.77600(19) 0.89683(17) 0.0481(6) Uani 1 1 d . . . . .
H22 H 0.164060 0.814046 0.854131 0.058 Uiso 1 1 calc R U . . .
C23 C 0.6007(3) 0.59676(16) 0.76533(18) 0.0422(5) Uani 1 1 d . . . . .
C24 C 0.7532(4) 0.59691(19) 0.8325(2) 0.0541(7) Uani 1 1 d . . . . .
H24 H 0.782561 0.651149 0.882698 0.065 Uiso 1 1 calc R U . . .
C25 C 0.8613(4) 0.5165(2) 0.8247(3) 0.0680(9) Uani 1 1 d . . . . .
H25 H 0.963388 0.516768 0.869494 0.082 Uiso 1 1 calc R U . . .
C26 C 0.8175(5) 0.4368(2) 0.7508(3) 0.0720(10) Uani 1 1 d . . . . .
H26 H 0.889747 0.382749 0.745874 0.086 Uiso 1 1 calc R U . . .
C27 C 0.6689(5) 0.4359(2) 0.6844(3) 0.0710(9) Uani 1 1 d . . . . .
H27 H 0.640715 0.381063 0.634683 0.085 Uiso 1 1 calc R U . . .
C28 C 0.5583(4) 0.51662(18) 0.6904(2) 0.0540(6) Uani 1 1 d . . . . .
H28 H 0.458037 0.516201 0.644552 0.065 Uiso 1 1 calc R U . . .
C29 C 0.1356(4) 0.62196(18) 0.66333(17) 0.0460(6) Uani 1 1 d . . . . .
H29 H 0.116919 0.583220 0.705539 0.055 Uiso 1 1 calc R U . . .
C30 C 0.0076(4) 0.6110(2) 0.58455(19) 0.0540(6) Uani 1 1 d . . . . .
H30 H -0.097244 0.564376 0.573369 0.065 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 1.793(2) . ?
Se1 N4 1.784(2) . ?
P1 C10 1.796(2) . ?
P1 C11 1.796(2) . ?
P1 C18 1.792(2) . ?
P1 C23 1.795(2) . ?
N1 C1 1.318(3) . ?
N2 C1 1.366(3) . ?
N2 C2 1.300(3) . ?
N3 C3 1.301(3) . ?
N3 C4 1.364(3) . ?
N4 C4 1.333(3) . ?
N5 C5 1.131(4) . ?
N6 C6 1.132(4) . ?
C1 C4 1.443(3) . ?
C2 C3 1.443(4) . ?
C2 C6 1.453(4) . ?
C3 C5 1.453(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(4) . ?
C7 C19 1.370(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(3) . ?
C10 C20 1.390(3) . ?
C11 C12 1.385(3) . ?
C11 C22 1.392(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(5) . ?
C14 H14 0.9300 . ?
C14 C21 1.374(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(4) . ?
C15 C30 1.382(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 C29 1.394(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.376(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.392(4) . ?
C23 C28 1.380(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.367(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.363(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.401(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.378(4) . ?
C30 H30 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
N4 Se1 N1 94.93(10) . . ?
C10 P1 C11 110.23(10) . . ?
C18 P1 C10 109.43(10) . . ?
C18 P1 C11 108.69(11) . . ?
C18 P1 C23 110.26(11) . . ?
C23 P1 C10 108.35(11) . . ?
C23 P1 C11 109.87(11) . . ?
C1 N1 Se1 106.02(16) . . ?
C2 N2 C1 114.0(2) . . ?
C3 N3 C4 114.1(2) . . ?
C4 N4 Se1 105.56(16) . . ?
N1 C1 N2 121.4(2) . . ?
N1 C1 C4 116.6(2) . . ?
N2 C1 C4 122.0(2) . . ?
N2 C2 C3 124.0(2) . . ?
N2 C2 C6 117.5(2) . . ?
C3 C2 C6 118.4(2) . . ?
N3 C3 C2 123.7(2) . . ?
N3 C3 C5 117.2(2) . . ?
C2 C3 C5 119.1(2) . . ?
N3 C4 C1 122.1(2) . . ?
N4 C4 N3 121.0(2) . . ?
N4 C4 C1 116.9(2) . . ?
N5 C5 C3 179.0(3) . . ?
N6 C6 C2 177.6(4) . . ?
C8 C7 H7 120.0 . . ?
C19 C7 H7 120.0 . . ?
C19 C7 C8 120.0(2) . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 P1 121.53(18) . . ?
C20 C10 P1 118.98(18) . . ?
C20 C10 C9 119.5(2) . . ?
C12 C11 P1 122.15(19) . . ?
C12 C11 C22 119.8(2) . . ?
C22 C11 P1 118.02(18) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 118.9(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C21 120.0(3) . . ?
C21 C14 H14 120.0 . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C30 120.1(3) . . ?
C30 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 P1 122.20(18) . . ?
C17 C18 C29 119.5(2) . . ?
C29 C18 P1 118.32(18) . . ?
C7 C19 H19 119.9 . . ?
C7 C19 C20 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C10 C20 H20 119.9 . . ?
C19 C20 C10 120.1(2) . . ?
C19 C20 H20 119.9 . . ?
C14 C21 H21 119.9 . . ?
C14 C21 C22 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C11 C22 H22 119.9 . . ?
C21 C22 C11 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C24 C23 P1 118.34(19) . . ?
C28 C23 P1 121.8(2) . . ?
C28 C23 C24 119.9(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.7(3) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.7(3) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.7(3) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 C27 118.8(3) . . ?
C23 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C18 C29 H29 120.2 . . ?
C30 C29 C18 119.7(2) . . ?
C30 C29 H29 120.2 . . ?
C15 C30 H30 119.9 . . ?
C29 C30 C15 120.3(3) . . ?
C29 C30 H30 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 N1 C1 N2 177.46(18) . . . . ?
Se1 N1 C1 C4 -0.8(3) . . . . ?
Se1 N4 C4 N3 179.66(18) . . . . ?
Se1 N4 C4 C1 -0.1(3) . . . . ?
P1 C10 C20 C19 177.88(19) . . . . ?
P1 C11 C12 C13 176.0(2) . . . . ?
P1 C11 C22 C21 -176.5(2) . . . . ?
P1 C18 C29 C30 -178.28(19) . . . . ?
P1 C23 C24 C25 177.9(2) . . . . ?
P1 C23 C28 C27 -177.4(2) . . . . ?
N1 Se1 N4 C4 -0.33(18) . . . . ?
N1 C1 C4 N3 -179.1(2) . . . . ?
N1 C1 C4 N4 0.6(3) . . . . ?
N2 C1 C4 N3 2.6(4) . . . . ?
N2 C1 C4 N4 -177.6(2) . . . . ?
N2 C2 C3 N3 2.5(4) . . . . ?
N2 C2 C3 C5 -178.3(2) . . . . ?
N4 Se1 N1 C1 0.66(18) . . . . ?
C1 N2 C2 C3 -1.5(3) . . . . ?
C1 N2 C2 C6 176.4(2) . . . . ?
C2 N2 C1 N1 -179.1(2) . . . . ?
C2 N2 C1 C4 -0.9(3) . . . . ?
C3 N3 C4 N4 178.6(2) . . . . ?
C3 N3 C4 C1 -1.7(3) . . . . ?
C4 N3 C3 C2 -0.7(3) . . . . ?
C4 N3 C3 C5 -179.9(2) . . . . ?
C6 C2 C3 N3 -175.4(2) . . . . ?
C6 C2 C3 C5 3.8(4) . . . . ?
C7 C8 C9 C10 -1.8(5) . . . . ?
C7 C19 C20 C10 -1.1(4) . . . . ?
C8 C7 C19 C20 0.9(4) . . . . ?
C8 C9 C10 P1 -176.4(2) . . . . ?
C8 C9 C10 C20 1.6(4) . . . . ?
C9 C10 C20 C19 -0.2(4) . . . . ?
C10 P1 C11 C12 -108.2(2) . . . . ?
C10 P1 C11 C22 69.3(2) . . . . ?
C10 P1 C18 C17 11.5(2) . . . . ?
C10 P1 C18 C29 -169.28(18) . . . . ?
C10 P1 C23 C24 53.0(2) . . . . ?
C10 P1 C23 C28 -128.5(2) . . . . ?
C11 P1 C10 C9 -20.4(2) . . . . ?
C11 P1 C10 C20 161.54(19) . . . . ?
C11 P1 C18 C17 131.9(2) . . . . ?
C11 P1 C18 C29 -48.8(2) . . . . ?
C11 P1 C23 C24 -67.5(2) . . . . ?
C11 P1 C23 C28 111.0(2) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C11 C22 C21 1.0(4) . . . . ?
C12 C13 C14 C21 1.5(5) . . . . ?
C13 C14 C21 C22 -2.0(5) . . . . ?
C14 C21 C22 C11 0.7(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C15 C30 C29 -0.1(4) . . . . ?
C16 C17 C18 P1 178.2(2) . . . . ?
C16 C17 C18 C29 -1.0(4) . . . . ?
C17 C18 C29 C30 1.0(4) . . . . ?
C18 P1 C10 C9 99.0(2) . . . . ?
C18 P1 C10 C20 -79.0(2) . . . . ?
C18 P1 C11 C12 131.9(2) . . . . ?
C18 P1 C11 C22 -50.7(2) . . . . ?
C18 P1 C23 C24 172.76(19) . . . . ?
C18 P1 C23 C28 -8.8(2) . . . . ?
C18 C29 C30 C15 -0.4(4) . . . . ?
C19 C7 C8 C9 0.6(5) . . . . ?
C22 C11 C12 C13 -1.4(4) . . . . ?
C23 P1 C10 C9 -140.7(2) . . . . ?
C23 P1 C10 C20 41.3(2) . . . . ?
C23 P1 C11 C12 11.1(2) . . . . ?
C23 P1 C11 C22 -171.40(18) . . . . ?
C23 P1 C18 C17 -107.6(2) . . . . ?
C23 P1 C18 C29 71.6(2) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C24 C23 C28 C27 1.0(4) . . . . ?
C24 C25 C26 C27 0.4(5) . . . . ?
C25 C26 C27 C28 0.1(5) . . . . ?
C26 C27 C28 C23 -0.8(4) . . . . ?
C28 C23 C24 C25 -0.6(4) . . . . ?
C30 C15 C16 C17 0.1(4) . . . . ?

####################################################################### 
# 
# 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-Br_Me3BnN
_database_code_depnum_ccdc_archive 'CCDC 2168142'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Radiush'
;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-22
_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            
;
trimethylbenzilammonium 1-bromo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_name_systematic        
;
trimethylbenzilammonium 1-bromo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide
;
_chemical_formula_moiety         'C6 N6 Se, Br, C10 H16 N'
_chemical_formula_sum            'C16 H16 Br N7 Se'
_chemical_formula_weight         465.23
_chemical_absolute_configuration ?
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.8387(14)
_cell_length_b                   6.5947(7)
_cell_length_c                   14.4796(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.018(5)
_cell_angle_gamma                90
_cell_volume                     938.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.190
_exptl_absorpt_coefficient_mu    4.141
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.7051.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle-plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9256
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         2.463
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                2904
_reflns_number_total             3864
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.23(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3864
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.033
_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)+(0.0265P)²+0.1148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0691
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.77(2)
 0.23(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C13(H13), C14(H14), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.32376(4) -0.01198(14) 0.01469(3) 0.03184(14) Uani 1 1 d . . . . .
Br1 Br 0.21344(5) -0.01153(17) -0.19379(3) 0.05156(17) Uani 1 1 d . . . . .
N1 N 0.7138(3) -0.0114(15) 0.0381(2) 0.0313(8) Uani 1 1 d . . . . .
N2 N 0.5905(3) -0.0120(17) 0.2149(2) 0.0354(8) Uani 1 1 d . . . . .
N3 N 0.3786(3) -0.0117(15) 0.1336(2) 0.0333(8) Uani 1 1 d . . . . .
N4 N 0.4923(3) -0.0156(17) -0.0281(2) 0.0325(8) Uani 1 1 d . . . . .
N17 N 0.7739(4) 0.9860(17) 0.7207(3) 0.0435(10) Uani 1 1 d . . . . .
C1 C 0.7829(4) -0.009(2) 0.1158(3) 0.0322(10) Uani 1 1 d . . . . .
C2 C 0.7216(4) -0.008(2) 0.2050(3) 0.0345(10) Uani 1 1 d . . . . .
C3 C 0.5139(4) -0.0098(19) 0.1343(3) 0.0287(9) Uani 1 1 d . . . . .
C4 C 0.5750(4) -0.0115(19) 0.0456(3) 0.0277(9) Uani 1 1 d . . . . .
C5 C 0.9299(5) -0.002(2) 0.1109(3) 0.0410(12) Uani 1 1 d . . . . .
C6 C 0.8099(6) 0.7606(9) 0.7033(4) 0.0416(15) Uani 1 1 d . . . . .
H6A H 0.908223 0.747965 0.704929 0.050 Uiso 1 1 calc R U . . .
H6B H 0.776599 0.680820 0.753987 0.050 Uiso 1 1 calc R U . . .
C7 C 0.6638(6) 0.466(2) 0.4577(4) 0.060(2) Uani 1 1 d . . . . .
H7 H 0.633058 0.396288 0.405251 0.072 Uiso 1 1 calc R U . . .
N6 N 1.0444(5) 0.006(2) 0.1058(3) 0.0617(16) Uani 1 1 d . . . . .
C8 C 0.8088(5) -0.008(3) 0.2875(4) 0.0480(12) Uani 1 1 d . . . . .
C9 C 0.5856(6) 0.474(2) 0.5335(4) 0.0566(16) Uani 1 1 d . . . . .
H9 H 0.500401 0.413389 0.532086 0.068 Uiso 1 1 calc R U . . .
N7 N 0.8790(6) -0.003(2) 0.3515(4) 0.0767(16) Uani 1 1 d . . . . .
C10 C 0.6242(6) 1.016(2) 0.7160(5) 0.067(3) Uani 1 1 d . . . . .
H10A H 0.582739 0.928848 0.760038 0.100 Uiso 1 1 calc R U . . .
H10B H 0.603637 1.154780 0.730008 0.100 Uiso 1 1 calc R U . . .
H10C H 0.589344 0.984006 0.654978 0.100 Uiso 1 1 calc R U . . .
C11 C 0.7561(6) 0.6705(8) 0.6153(4) 0.0357(13) Uani 1 1 d . . . . .
C12 C 0.8270(7) 1.0334(17) 0.8161(5) 0.087(4) Uani 1 1 d . . . . .
H12A H 0.782272 0.948852 0.859673 0.130 Uiso 1 1 calc R U . . .
H12B H 0.923140 1.008507 0.820228 0.130 Uiso 1 1 calc R U . . .
H12C H 0.809626 1.173242 0.829791 0.130 Uiso 1 1 calc R U . . .
C13 C 0.7873(7) 0.5611(11) 0.4588(5) 0.065(2) Uani 1 1 d . . . . .
H13 H 0.840629 0.557171 0.407023 0.078 Uiso 1 1 calc R U . . .
C14 C 0.6321(6) 0.5720(8) 0.6116(4) 0.0451(16) Uani 1 1 d . . . . .
H14 H 0.579009 0.572063 0.663454 0.054 Uiso 1 1 calc R U . . .
C18 C 0.8322(6) 0.6625(11) 0.5371(4) 0.0506(16) Uani 1 1 d . . . . .
H18 H 0.916120 0.727492 0.537324 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8430(9) 1.1161(10) 0.6545(6) 0.084(3) Uani 1 1 d . . . . .
H15A H 0.939248 1.092501 0.659487 0.125 Uiso 1 1 calc R U . . .
H15B H 0.810255 1.085018 0.592860 0.125 Uiso 1 1 calc R U . . .
H15C H 0.824547 1.255792 0.667889 0.125 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 N3 1.786(3) . ?
Se1 N4 1.791(3) . ?
N1 C1 1.294(5) . ?
N1 C4 1.374(5) . ?
N2 C2 1.303(5) . ?
N2 C3 1.367(5) . ?
N3 C3 1.331(5) . ?
N4 C4 1.319(5) . ?
N17 C6 1.550(11) . ?
N17 C10 1.486(7) . ?
N17 C12 1.493(8) . ?
N17 C15 1.470(9) . ?
C1 C2 1.445(6) . ?
C1 C5 1.451(6) . ?
C2 C8 1.445(7) . ?
C3 C4 1.436(5) . ?
C5 N6 1.132(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C11 1.486(8) . ?
C7 H7 0.9300 . ?
C7 C9 1.364(8) . ?
C7 C13 1.366(11) . ?
C8 N7 1.136(6) . ?
C9 H9 0.9300 . ?
C9 C14 1.365(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C14 1.382(8) . ?
C11 C18 1.381(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C18 1.375(9) . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
N3 Se1 N4 94.65(15) . . ?
C1 N1 C4 115.1(3) . . ?
C2 N2 C3 115.1(3) . . ?
C3 N3 Se1 106.0(3) . . ?
C4 N4 Se1 105.8(3) . . ?
C10 N17 C6 110.6(8) . . ?
C10 N17 C12 109.1(5) . . ?
C12 N17 C6 106.1(7) . . ?
C15 N17 C6 109.9(5) . . ?
C15 N17 C10 111.9(8) . . ?
C15 N17 C12 109.1(7) . . ?
N1 C1 C2 123.7(4) . . ?
N1 C1 C5 116.8(4) . . ?
C2 C1 C5 119.5(4) . . ?
N2 C2 C1 122.9(4) . . ?
N2 C2 C8 118.1(4) . . ?
C1 C2 C8 119.0(4) . . ?
N2 C3 C4 121.9(3) . . ?
N3 C3 N2 121.8(3) . . ?
N3 C3 C4 116.3(4) . . ?
N1 C4 C3 121.3(4) . . ?
N4 C4 N1 121.5(3) . . ?
N4 C4 C3 117.2(3) . . ?
N6 C5 C1 178.8(13) . . ?
N17 C6 H6A 108.2 . . ?
N17 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
C11 C6 N17 116.5(5) . . ?
C11 C6 H6A 108.2 . . ?
C11 C6 H6B 108.2 . . ?
C9 C7 H7 120.0 . . ?
C9 C7 C13 119.9(9) . . ?
C13 C7 H7 120.0 . . ?
N7 C8 C2 177.6(18) . . ?
C7 C9 H9 119.9 . . ?
C7 C9 C14 120.2(8) . . ?
C14 C9 H9 119.9 . . ?
N17 C10 H10A 109.5 . . ?
N17 C10 H10B 109.5 . . ?
N17 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C11 C6 120.6(5) . . ?
C18 C11 C6 122.1(5) . . ?
C18 C11 C14 117.0(6) . . ?
N17 C12 H12A 109.5 . . ?
N17 C12 H12B 109.5 . . ?
N17 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13 120.3 . . ?
C7 C13 C18 119.4(6) . . ?
C18 C13 H13 120.3 . . ?
C9 C14 C11 121.6(6) . . ?
C9 C14 H14 119.2 . . ?
C11 C14 H14 119.2 . . ?
C11 C18 H18 119.1 . . ?
C13 C18 C11 121.8(6) . . ?
C13 C18 H18 119.1 . . ?
N17 C15 H15A 109.5 . . ?
N17 C15 H15B 109.5 . . ?
N17 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 N3 C3 N2 -179.0(9) . . . . ?
Se1 N3 C3 C4 -0.9(14) . . . . ?
Se1 N4 C4 N1 -179.6(10) . . . . ?
Se1 N4 C4 C3 1.2(15) . . . . ?
N1 C1 C2 N2 1(2) . . . . ?
N1 C1 C2 C8 178.9(14) . . . . ?
N2 C3 C4 N1 -1(2) . . . . ?
N2 C3 C4 N4 177.9(12) . . . . ?
N3 Se1 N4 C4 -1.4(9) . . . . ?
N3 C3 C4 N1 -179.5(10) . . . . ?
N3 C3 C4 N4 -0.3(18) . . . . ?
N4 Se1 N3 C3 1.3(9) . . . . ?
N17 C6 C11 C14 -91.7(7) . . . . ?
N17 C6 C11 C18 95.0(7) . . . . ?
C1 N1 C4 N4 -179.4(13) . . . . ?
C1 N1 C4 C3 -0.3(18) . . . . ?
C2 N2 C3 N3 -179.3(13) . . . . ?
C2 N2 C3 C4 2.6(18) . . . . ?
C3 N2 C2 C1 -3(2) . . . . ?
C3 N2 C2 C8 179.7(12) . . . . ?
C4 N1 C1 C2 0.4(19) . . . . ?
C4 N1 C1 C5 -178.1(13) . . . . ?
C5 C1 C2 N2 179.5(14) . . . . ?
C5 C1 C2 C8 -3(2) . . . . ?
C6 C11 C14 C9 -174.8(8) . . . . ?
C6 C11 C18 C13 173.4(6) . . . . ?
C7 C9 C14 C11 2.3(16) . . . . ?
C7 C13 C18 C11 0.4(12) . . . . ?
C9 C7 C13 C18 0.6(17) . . . . ?
C10 N17 C6 C11 56.2(7) . . . . ?
C12 N17 C6 C11 174.4(5) . . . . ?
C13 C7 C9 C14 -1.9(19) . . . . ?
C14 C11 C18 C13 -0.1(9) . . . . ?
C18 C11 C14 C9 -1.2(10) . . . . ?
C15 N17 C6 C11 -67.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.77(2)
2 0.23(2)
####################################################################### 
# 
# 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-Br_K(18-c-6)
_database_code_depnum_ccdc_archive 'CCDC 2168139'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Radiush'
;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;      	
potassium 1-bromo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide potassium with 18-crown-6
;
_chemical_name_common            
;
potassium 1-bromo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide potassium with 18-crown-6
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 Br K N6 O6 Se'
_chemical_formula_weight         618.40

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'
K K 0.2009 0.2494 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5052(5)
_cell_length_b                   10.9758(8)
_cell_length_c                   16.5976(17)
_cell_angle_alpha                106.379(7)
_cell_angle_beta                 92.267(8)
_cell_angle_gamma                104.840(7)
_cell_volume                     1258.75(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    173
_cell_measurement_reflns_used    179
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      25.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    3.288
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
SCXMini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury2 (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            10614
_diffrn_reflns_av_unetI/netI     0.032
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.749
_diffrn_reflns_theta_max         25.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             4522
_reflns_number_gt                3790
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+0.0208P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4522
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0594
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br34 Br 0.03858(3) 0.45442(2) 0.31052(2) 0.04803(8) Uani 1 1 d . . . . .
Se3 Se 0.84638(3) 0.62161(2) 0.51785(2) 0.04169(7) Uani 1 1 d . . . . .
K14 K 1.000000 1.000000 0.500000 0.04338(14) Uani 1 2 d S . P . .
K24 K 0.000000 0.000000 0.000000 0.03824(13) Uani 1 2 d S . P . .
O16 O 0.9698(2) 1.02404(14) 0.67374(8) 0.0524(4) Uani 1 1 d . . . . .
O19 O 1.17155(18) 0.86312(13) 0.57930(8) 0.0451(3) Uani 1 1 d . . . . .
O22 O 1.26202(19) 0.88986(13) 0.41949(9) 0.0470(3) Uani 1 1 d . . . . .
O26 O -0.1045(2) -0.23051(14) 0.04201(10) 0.0581(4) Uani 1 1 d . . . . .
O29 O -0.27109(18) -0.03450(13) 0.10860(9) 0.0484(3) Uani 1 1 d . . . . .
O32 O -0.21499(18) 0.17974(12) 0.04051(8) 0.0430(3) Uani 1 1 d . . . . .
N2 N 0.7904(2) 0.69732(14) 0.44135(10) 0.0416(4) Uani 1 1 d . . . . .
N4 N 0.6957(2) 0.46258(14) 0.46500(10) 0.0387(3) Uani 1 1 d . . . . .
N6 N 0.5021(2) 0.36539(14) 0.33619(9) 0.0348(3) Uani 1 1 d . . . . .
N9 N 0.5973(2) 0.62411(15) 0.31244(10) 0.0398(3) Uani 1 1 d . . . . .
N11 N 0.2345(2) 0.19020(17) 0.15074(11) 0.0515(4) Uani 1 1 d . . . . .
N13 N 0.3407(3) 0.5491(2) 0.12364(15) 0.0787(7) Uani 1 1 d . . . . .
C1 C 0.6701(2) 0.60131(16) 0.38163(11) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.6205(2) 0.47328(17) 0.39457(11) 0.0316(4) Uani 1 1 d . . . . .
C7 C 0.4357(2) 0.39077(16) 0.27078(11) 0.0330(4) Uani 1 1 d . . . . .
C8 C 0.4818(2) 0.51928(18) 0.25899(11) 0.0378(4) Uani 1 1 d . . . . .
C10 C 0.3169(3) 0.27894(19) 0.20443(12) 0.0391(4) Uani 1 1 d . . . . .
C12 C 0.3996(3) 0.5372(2) 0.18385(14) 0.0505(5) Uani 1 1 d . . . . .
C15 C 0.8033(3) 1.0497(3) 0.70148(14) 0.0626(6) Uani 1 1 d . . . . .
H15A H 0.814148 1.076157 0.762781 0.075 Uiso 1 1 calc R U . . .
H15B H 0.700622 0.970244 0.679779 0.075 Uiso 1 1 calc R U . . .
C17 C 1.0113(4) 0.9195(2) 0.69831(13) 0.0580(6) Uani 1 1 d . . . . .
H17A H 0.913261 0.838108 0.673445 0.070 Uiso 1 1 calc R U . . .
H17B H 1.019837 0.939704 0.759361 0.070 Uiso 1 1 calc R U . . .
C18 C 1.1889(4) 0.9033(2) 0.66931(13) 0.0598(6) Uani 1 1 d . . . . .
H18A H 1.285223 0.986214 0.691772 0.072 Uiso 1 1 calc R U . . .
H18B H 1.223990 0.837300 0.689912 0.072 Uiso 1 1 calc R U . . .
C20 C 1.3439(3) 0.8552(2) 0.54864(15) 0.0520(5) Uani 1 1 d . . . . .
H20A H 1.395347 0.799615 0.573451 0.062 Uiso 1 1 calc R U . . .
H20B H 1.431050 0.942751 0.565218 0.062 Uiso 1 1 calc R U . . .
C21 C 1.3177(3) 0.7997(2) 0.45544(15) 0.0533(5) Uani 1 1 d . . . . .
H21A H 1.432784 0.785707 0.435551 0.064 Uiso 1 1 calc R U . . .
H21B H 1.223422 0.715236 0.438324 0.064 Uiso 1 1 calc R U . . .
C23 C 1.2320(4) 0.8437(3) 0.32921(14) 0.0634(6) Uani 1 1 d . . . . .
H23A H 1.126415 0.765720 0.310282 0.076 Uiso 1 1 calc R U . . .
H23B H 1.340437 0.820427 0.306976 0.076 Uiso 1 1 calc R U . . .
C25 C 0.0317(3) -0.2997(2) 0.04090(16) 0.0594(6) Uani 1 1 d . . . . .
H25A H -0.025173 -0.387640 0.044451 0.071 Uiso 1 1 calc R U . . .
H25B H 0.126280 -0.253229 0.088981 0.071 Uiso 1 1 calc R U . . .
C27 C -0.2223(3) -0.2397(2) 0.10555(18) 0.0665(6) Uani 1 1 d . . . . .
H27A H -0.149824 -0.201282 0.160846 0.080 Uiso 1 1 calc R U . . .
H27B H -0.283737 -0.331811 0.098832 0.080 Uiso 1 1 calc R U . . .
C28 C -0.3628(3) -0.1683(2) 0.09907(16) 0.0604(6) Uani 1 1 d . . . . .
H28A H -0.438105 -0.208493 0.044489 0.073 Uiso 1 1 calc R U . . .
H28B H -0.443928 -0.173773 0.142784 0.073 Uiso 1 1 calc R U . . .
C30 C -0.3930(3) 0.0467(2) 0.11653(13) 0.0481(5) Uani 1 1 d . . . . .
H30A H -0.451491 0.049723 0.167874 0.058 Uiso 1 1 calc R U . . .
H30B H -0.489623 0.010694 0.068774 0.058 Uiso 1 1 calc R U . . .
C31 C -0.2843(3) 0.1825(2) 0.11936(13) 0.0492(5) Uani 1 1 d . . . . .
H31A H -0.363012 0.241565 0.131050 0.059 Uiso 1 1 calc R U . . .
H31B H -0.181715 0.215404 0.164351 0.059 Uiso 1 1 calc R U . . .
C33 C -0.1170(3) 0.3087(2) 0.03934(15) 0.0571(6) Uani 1 1 d . . . . .
H33A H -0.020906 0.349561 0.087224 0.068 Uiso 1 1 calc R U . . .
H33B H -0.201688 0.363201 0.043818 0.068 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
Se3 N4 1.7725(15) . ?
Se3 N2 1.7920(16) . ?
K14 O19 2.7602(13) 2_776 ?
K14 O19 2.7602(13) . ?
K14 O22 2.7620(14) . ?
K14 O22 2.7621(14) 2_776 ?
K14 O16 2.8442(14) 2_776 ?
K14 O16 2.8443(14) . ?
K14 N2 3.1365(15) . ?
K14 N2 3.1365(15) 2_776 ?
K14 C20 3.535(2) 2_776 ?
K14 C20 3.535(2) . ?
K24 O26 2.7430(14) 2 ?
K24 O26 2.7431(14) . ?
K24 O29 2.7950(13) 2 ?
K24 O29 2.7951(13) . ?
K24 O32 2.8135(13) . ?
K24 O32 2.8135(13) 2 ?
K24 N11 2.9223(17) . ?
K24 N11 2.9223(17) 2 ?
O16 C15 1.416(3) . ?
O16 C17 1.420(3) . ?
O19 C20 1.423(3) . ?
O19 C18 1.424(3) . ?
O22 C21 1.426(3) . ?
O22 C23 1.428(3) . ?
O26 C27 1.412(3) . ?
O26 C25 1.419(3) . ?
O29 C28 1.414(3) . ?
O29 C30 1.418(2) . ?
O32 C31 1.423(2) . ?
O32 C33 1.424(2) . ?
N2 C1 1.327(2) . ?
N4 C5 1.326(2) . ?
N6 C7 1.305(2) . ?
N6 C5 1.370(2) . ?
N9 C8 1.310(2) . ?
N9 C1 1.365(2) . ?
N11 C10 1.133(2) . ?
N13 C12 1.131(3) . ?
C1 C5 1.438(2) . ?
C7 C8 1.435(3) . ?
C7 C10 1.454(2) . ?
C8 C12 1.454(3) . ?
C15 C23 1.477(4) 2_776 ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.471(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C21 1.478(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C25 C33 1.489(3) 2 ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C27 C28 1.483(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C30 C31 1.491(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Se3 N2 95.41(7) . . ?
O19 K14 O19 180.0 2_776 . ?
O19 K14 O22 118.11(4) 2_776 . ?
O19 K14 O22 61.89(4) . . ?
O19 K14 O22 61.89(4) 2_776 2_776 ?
O19 K14 O22 118.11(4) . 2_776 ?
O22 K14 O22 180.0 . 2_776 ?
O19 K14 O16 60.04(4) 2_776 2_776 ?
O19 K14 O16 119.96(4) . 2_776 ?
O22 K14 O16 59.60(4) . 2_776 ?
O22 K14 O16 120.41(4) 2_776 2_776 ?
O19 K14 O16 119.96(4) 2_776 . ?
O19 K14 O16 60.04(4) . . ?
O22 K14 O16 120.40(4) . . ?
O22 K14 O16 59.60(4) 2_776 . ?
O16 K14 O16 180.00(6) 2_776 . ?
O19 K14 N2 111.17(4) 2_776 . ?
O19 K14 N2 68.83(4) . . ?
O22 K14 N2 77.89(4) . . ?
O22 K14 N2 102.11(4) 2_776 . ?
O16 K14 N2 86.99(4) 2_776 . ?
O16 K14 N2 93.01(4) . . ?
O19 K14 N2 68.83(4) 2_776 2_776 ?
O19 K14 N2 111.17(4) . 2_776 ?
O22 K14 N2 102.11(4) . 2_776 ?
O22 K14 N2 77.89(4) 2_776 2_776 ?
O16 K14 N2 93.01(4) 2_776 2_776 ?
O16 K14 N2 86.99(4) . 2_776 ?
N2 K14 N2 180.0 . 2_776 ?
O19 K14 C20 22.02(5) 2_776 2_776 ?
O19 K14 C20 157.98(5) . 2_776 ?
O22 K14 C20 138.10(5) . 2_776 ?
O22 K14 C20 41.90(5) 2_776 2_776 ?
O16 K14 C20 78.52(5) 2_776 2_776 ?
O16 K14 C20 101.48(5) . 2_776 ?
N2 K14 C20 102.80(4) . 2_776 ?
N2 K14 C20 77.20(4) 2_776 2_776 ?
O19 K14 C20 157.98(5) 2_776 . ?
O19 K14 C20 22.02(5) . . ?
O22 K14 C20 41.90(5) . . ?
O22 K14 C20 138.10(5) 2_776 . ?
O16 K14 C20 101.48(5) 2_776 . ?
O16 K14 C20 78.52(5) . . ?
N2 K14 C20 77.20(4) . . ?
N2 K14 C20 102.80(4) 2_776 . ?
C20 K14 C20 180.00(5) 2_776 . ?
O26 K24 O26 180.0 2 . ?
O26 K24 O29 59.52(4) 2 2 ?
O26 K24 O29 120.48(4) . 2 ?
O26 K24 O29 120.48(4) 2 . ?
O26 K24 O29 59.52(4) . . ?
O29 K24 O29 180.0 2 . ?
O26 K24 O32 60.94(4) 2 . ?
O26 K24 O32 119.06(4) . . ?
O29 K24 O32 119.38(4) 2 . ?
O29 K24 O32 60.62(4) . . ?
O26 K24 O32 119.06(4) 2 2 ?
O26 K24 O32 60.94(4) . 2 ?
O29 K24 O32 60.62(4) 2 2 ?
O29 K24 O32 119.38(4) . 2 ?
O32 K24 O32 180.0 . 2 ?
O26 K24 N11 75.89(5) 2 . ?
O26 K24 N11 104.11(5) . . ?
O29 K24 N11 94.76(5) 2 . ?
O29 K24 N11 85.24(5) . . ?
O32 K24 N11 81.19(5) . . ?
O32 K24 N11 98.81(5) 2 . ?
O26 K24 N11 104.11(5) 2 2 ?
O26 K24 N11 75.89(5) . 2 ?
O29 K24 N11 85.24(5) 2 2 ?
O29 K24 N11 94.76(5) . 2 ?
O32 K24 N11 98.81(5) . 2 ?
O32 K24 N11 81.19(5) 2 2 ?
N11 K24 N11 180.00(6) . 2 ?
C15 O16 C17 112.92(17) . . ?
C15 O16 K14 114.50(12) . . ?
C17 O16 K14 113.11(12) . . ?
C20 O19 C18 111.65(16) . . ?
C20 O19 K14 111.31(11) . . ?
C18 O19 K14 116.65(12) . . ?
C21 O22 C23 112.91(17) . . ?
C21 O22 K14 114.83(12) . . ?
C23 O22 K14 116.50(12) . . ?
C27 O26 C25 113.89(18) . . ?
C27 O26 K24 119.72(13) . . ?
C25 O26 K24 116.29(12) . . ?
C28 O29 C30 113.35(15) . . ?
C28 O29 K24 113.98(12) . . ?
C30 O29 K24 116.60(11) . . ?
C31 O32 C33 111.51(15) . . ?
C31 O32 K24 110.76(11) . . ?
C33 O32 K24 112.41(11) . . ?
C1 N2 Se3 105.47(12) . . ?
C1 N2 K14 144.28(12) . . ?
Se3 N2 K14 110.22(6) . . ?
C5 N4 Se3 105.34(12) . . ?
C7 N6 C5 114.22(15) . . ?
C8 N9 C1 114.13(15) . . ?
C10 N11 K24 168.69(17) . . ?
N2 C1 N9 121.44(16) . . ?
N2 C1 C5 116.20(16) . . ?
N9 C1 C5 122.36(15) . . ?
N4 C5 N6 120.78(15) . . ?
N4 C5 C1 117.52(15) . . ?
N6 C5 C1 121.69(15) . . ?
N6 C7 C8 123.97(16) . . ?
N6 C7 C10 116.81(16) . . ?
C8 C7 C10 119.11(16) . . ?
N9 C8 C7 123.58(17) . . ?
N9 C8 C12 116.73(17) . . ?
C7 C8 C12 119.69(16) . . ?
N11 C10 C7 175.5(2) . . ?
N13 C12 C8 177.3(3) . . ?
O16 C15 C23 109.20(18) . 2_776 ?
O16 C15 H15A 109.8 . . ?
C23 C15 H15A 109.8 2_776 . ?
O16 C15 H15B 109.8 . . ?
C23 C15 H15B 109.8 2_776 . ?
H15A C15 H15B 108.3 . . ?
O16 C17 C18 108.95(17) . . ?
O16 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
O16 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O19 C18 C17 109.83(17) . . ?
O19 C18 H18A 109.7 . . ?
C17 C18 H18A 109.7 . . ?
O19 C18 H18B 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
O19 C20 C21 110.37(16) . . ?
O19 C20 K14 46.66(8) . . ?
C21 C20 K14 80.56(11) . . ?
O19 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
K14 C20 H20A 155.8 . . ?
O19 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
K14 C20 H20B 87.8 . . ?
H20A C20 H20B 108.1 . . ?
O22 C21 C20 109.00(16) . . ?
O22 C21 H21A 109.9 . . ?
C20 C21 H21A 109.9 . . ?
O22 C21 H21B 109.9 . . ?
C20 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
O22 C23 C15 108.37(18) . 2_776 ?
O22 C23 H23A 110.0 . . ?
C15 C23 H23A 110.0 2_776 . ?
O22 C23 H23B 110.0 . . ?
C15 C23 H23B 110.0 2_776 . ?
H23A C23 H23B 108.4 . . ?
O26 C25 C33 108.58(19) . 2 ?
O26 C25 H25A 110.0 . . ?
C33 C25 H25A 110.0 2 . ?
O26 C25 H25B 110.0 . . ?
C33 C25 H25B 110.0 2 . ?
H25A C25 H25B 108.4 . . ?
O26 C27 C28 109.4(2) . . ?
O26 C27 H27A 109.8 . . ?
C28 C27 H27A 109.8 . . ?
O26 C27 H27B 109.8 . . ?
C28 C27 H27B 109.8 . . ?
H27A C27 H27B 108.2 . . ?
O29 C28 C27 109.06(18) . . ?
O29 C28 H28A 109.9 . . ?
C27 C28 H28A 109.9 . . ?
O29 C28 H28B 109.9 . . ?
C27 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
O29 C30 C31 108.79(16) . . ?
O29 C30 H30A 109.9 . . ?
C31 C30 H30A 109.9 . . ?
O29 C30 H30B 109.9 . . ?
C31 C30 H30B 109.9 . . ?
H30A C30 H30B 108.3 . . ?
O32 C31 C30 109.75(16) . . ?
O32 C31 H31A 109.7 . . ?
C30 C31 H31A 109.7 . . ?
O32 C31 H31B 109.7 . . ?
C30 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
O32 C33 C25 109.65(17) . 2 ?
O32 C33 H33A 109.7 . . ?
C25 C33 H33A 109.7 2 . ?
O32 C33 H33B 109.7 . . ?
C25 C33 H33B 109.7 2 . ?
H33A C33 H33B 108.2 . . ?

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
N4 Se3 N2 C1 -1.63(13) . . . . ?
N4 Se3 N2 K14 176.94(7) . . . . ?
N2 Se3 N4 C5 2.21(12) . . . . ?
Se3 N2 C1 N9 -179.86(14) . . . . ?
K14 N2 C1 N9 2.4(3) . . . . ?
Se3 N2 C1 C5 0.64(18) . . . . ?
K14 N2 C1 C5 -177.06(13) . . . . ?
C8 N9 C1 N2 179.53(16) . . . . ?
C8 N9 C1 C5 -1.0(2) . . . . ?
Se3 N4 C5 N6 176.87(13) . . . . ?
Se3 N4 C5 C1 -2.27(18) . . . . ?
C7 N6 C5 N4 178.70(16) . . . . ?
C7 N6 C5 C1 -2.2(2) . . . . ?
N2 C1 C5 N4 1.2(2) . . . . ?
N9 C1 C5 N4 -178.33(16) . . . . ?
N2 C1 C5 N6 -177.97(15) . . . . ?
N9 C1 C5 N6 2.5(3) . . . . ?
C5 N6 C7 C8 0.7(2) . . . . ?
C5 N6 C7 C10 176.84(15) . . . . ?
C1 N9 C8 C7 -0.6(3) . . . . ?
C1 N9 C8 C12 -179.95(17) . . . . ?
N6 C7 C8 N9 0.8(3) . . . . ?
C10 C7 C8 N9 -175.30(17) . . . . ?
N6 C7 C8 C12 -179.84(18) . . . . ?
C10 C7 C8 C12 4.1(3) . . . . ?
C17 O16 C15 C23 -178.12(17) . . . 2_776 ?
K14 O16 C15 C23 -46.7(2) . . . 2_776 ?
C15 O16 C17 C18 -178.09(17) . . . . ?
K14 O16 C17 C18 49.85(18) . . . . ?
C20 O19 C18 C17 175.89(16) . . . . ?
K14 O19 C18 C17 46.3(2) . . . . ?
O16 C17 C18 O19 -64.2(2) . . . . ?
C18 O19 C20 C21 173.93(16) . . . . ?
K14 O19 C20 C21 -53.77(17) . . . . ?
C18 O19 C20 K14 -132.29(16) . . . . ?
C23 O22 C21 C20 -179.58(17) . . . . ?
K14 O22 C21 C20 -42.75(19) . . . . ?
O19 C20 C21 O22 65.7(2) . . . . ?
K14 C20 C21 O22 29.20(13) . . . . ?
C21 O22 C23 C15 -173.50(18) . . . 2_776 ?
K14 O22 C23 C15 50.4(2) . . . 2_776 ?
C27 O26 C25 C33 167.19(19) . . . 2 ?
K24 O26 C25 C33 -47.4(2) . . . 2 ?
C25 O26 C27 C28 -177.98(19) . . . . ?
K24 O26 C27 C28 37.9(2) . . . . ?
C30 O29 C28 C27 -170.76(18) . . . . ?
K24 O29 C28 C27 52.7(2) . . . . ?
O26 C27 C28 O29 -59.2(3) . . . . ?
C28 O29 C30 C31 -175.61(17) . . . . ?
K24 O29 C30 C31 -40.28(18) . . . . ?
C33 O32 C31 C30 177.44(17) . . . . ?
K24 O32 C31 C30 -56.57(17) . . . . ?
O29 C30 C31 O32 65.7(2) . . . . ?
C31 O32 C33 C25 174.61(18) . . . 2 ?
K24 O32 C33 C25 49.5(2) . . . 2 ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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-I_K(18-c-6)
_database_code_depnum_ccdc_archive 'CCDC 2168140'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Radiush'
;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
;
potassium 1-iodo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide potassium with 18-crown-6
;
_chemical_name_systematic        
;
potassium 1-iodo-5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide potassium with 18-crown-6
;
_chemical_formula_moiety         'I, C18 H24 K N6 O6 Se'
_chemical_formula_sum            'C18 H24 I K N6 O6 Se'
_chemical_formula_weight         665.39
_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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8062(4)
_cell_length_b                   22.5996(14)
_cell_length_c                   14.9943(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.719(2)
_cell_angle_gamma                90
_cell_volume                     2580.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.481
_shelx_estimated_absorpt_T_min   0.183
_exptl_absorpt_coefficient_mu    2.856
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0899 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.5349.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34295
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         2.278
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4196
_reflns_number_total             5915
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.068
_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)+(0.0358P)²+0.9214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
  C17(H17A,H17B), C18(H18A,H18B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I1 I 0.37666(3) 0.40035(2) 0.33211(2) 0.04804(9) Uani 1 1 d . . . . .
Se1 Se 0.69209(4) 0.54459(2) 0.45423(2) 0.04356(10) Uani 1 1 d . . . . .
K1 K 0.89341(9) 0.14309(3) 0.28344(5) 0.04130(18) Uani 1 1 d . . . . .
N4 N 0.8967(3) 0.39331(11) 0.43008(17) 0.0342(6) Uani 1 1 d . . . . .
N3 N 0.8332(3) 0.45967(12) 0.26086(17) 0.0367(6) Uani 1 1 d . . . . .
O6 O 0.7586(3) 0.16012(11) 0.44008(16) 0.0503(6) Uani 1 1 d . . . . .
O5 O 0.5865(3) 0.20934(10) 0.26948(15) 0.0446(6) Uani 1 1 d . . . . .
O4 O 0.7750(3) 0.21834(11) 0.13441(15) 0.0479(6) Uani 1 1 d . . . . .
O3 O 1.0533(3) 0.14126(10) 0.13374(15) 0.0429(5) Uani 1 1 d . . . . .
O2 O 1.2149(3) 0.08568(10) 0.30235(16) 0.0463(6) Uani 1 1 d . . . . .
O1 O 1.0188(3) 0.07334(11) 0.43991(15) 0.0495(6) Uani 1 1 d . . . . .
N2 N 0.7882(3) 0.47547(12) 0.49544(17) 0.0391(6) Uani 1 1 d . . . . .
C2 C 0.8291(4) 0.44965(13) 0.4234(2) 0.0310(7) Uani 1 1 d . . . . .
C3 C 0.9275(4) 0.37240(14) 0.3533(2) 0.0316(7) Uani 1 1 d . . . . .
C6 C 0.9875(4) 0.31171(16) 0.3526(2) 0.0376(7) Uani 1 1 d . . . . .
N6 N 1.0242(4) 0.26333(14) 0.3500(2) 0.0537(8) Uani 1 1 d . . . . .
N1 N 0.7240(3) 0.53536(12) 0.33977(18) 0.0413(6) Uani 1 1 d . . . . .
C7 C 0.5772(5) 0.17566(18) 0.4179(3) 0.0555(10) Uani 1 1 d . . . . .
H7A H 0.538397 0.185581 0.473218 0.067 Uiso 1 1 calc R U . . .
H7B H 0.508184 0.142360 0.389063 0.067 Uiso 1 1 calc R U . . .
C8 C 0.5509(5) 0.22731(18) 0.3546(3) 0.0566(10) Uani 1 1 d . . . . .
H8A H 0.430956 0.241457 0.345493 0.068 Uiso 1 1 calc R U . . .
H8B H 0.629184 0.259240 0.380488 0.068 Uiso 1 1 calc R U . . .
C9 C 0.5523(5) 0.25516(16) 0.2029(3) 0.0528(9) Uani 1 1 d . . . . .
H9A H 0.624139 0.289459 0.224524 0.063 Uiso 1 1 calc R U . . .
H9B H 0.429832 0.266827 0.192024 0.063 Uiso 1 1 calc R U . . .
C10 C 0.5939(5) 0.23270(17) 0.1165(2) 0.0520(9) Uani 1 1 d . . . . .
H10A H 0.523888 0.197902 0.095443 0.062 Uiso 1 1 calc R U . . .
H10B H 0.567313 0.262758 0.069258 0.062 Uiso 1 1 calc R U . . .
C11 C 0.8355(5) 0.20710(16) 0.0534(2) 0.0492(9) Uani 1 1 d . . . . .
H11A H 0.815812 0.241517 0.013778 0.059 Uiso 1 1 calc R U . . .
H11B H 0.772128 0.173932 0.020635 0.059 Uiso 1 1 calc R U . . .
C12 C 1.0258(5) 0.19347(17) 0.0794(2) 0.0534(10) Uani 1 1 d . . . . .
H12A H 1.071245 0.187806 0.024751 0.064 Uiso 1 1 calc R U . . .
H12B H 1.088156 0.226319 0.113519 0.064 Uiso 1 1 calc R U . . .
C13 C 1.2362(5) 0.12572(17) 0.1590(2) 0.0504(9) Uani 1 1 d . . . . .
H13A H 1.302379 0.158159 0.192369 0.060 Uiso 1 1 calc R U . . .
H13B H 1.280574 0.118601 0.104415 0.060 Uiso 1 1 calc R U . . .
C14 C 1.2594(5) 0.07199(17) 0.2166(2) 0.0505(9) Uani 1 1 d . . . . .
H14A H 1.184140 0.040585 0.186014 0.061 Uiso 1 1 calc R U . . .
H14B H 1.380239 0.058587 0.227108 0.061 Uiso 1 1 calc R U . . .
C15 C 1.2302(5) 0.03607(17) 0.3613(3) 0.0589(10) Uani 1 1 d . . . . .
H15A H 1.346868 0.019123 0.370036 0.071 Uiso 1 1 calc R U . . .
H15B H 1.145206 0.006039 0.335055 0.071 Uiso 1 1 calc R U . . .
C16 C 1.1972(5) 0.05661(17) 0.4509(3) 0.0561(10) Uani 1 1 d . . . . .
H16A H 1.224453 0.025050 0.495659 0.067 Uiso 1 1 calc R U . . .
H16B H 1.272406 0.090063 0.473050 0.067 Uiso 1 1 calc R U . . .
C17 C 0.9826(5) 0.09733(18) 0.5215(2) 0.0580(10) Uani 1 1 d . . . . .
H17A H 1.054322 0.132176 0.539634 0.070 Uiso 1 1 calc R U . . .
H17B H 1.010674 0.068458 0.570389 0.070 Uiso 1 1 calc R U . . .
C18 C 0.7933(6) 0.1134(2) 0.5052(3) 0.0688(12) Uani 1 1 d . . . . .
H18A H 0.721483 0.079274 0.482390 0.083 Uiso 1 1 calc R U . . .
H18B H 0.764582 0.125907 0.562018 0.083 Uiso 1 1 calc R U . . .
C4 C 0.8974(4) 0.40621(14) 0.2696(2) 0.0340(7) Uani 1 1 d . . . . .
C1 C 0.7955(4) 0.48221(14) 0.33877(19) 0.0319(7) Uani 1 1 d . . . . .
C5 C 0.9315(4) 0.37787(17) 0.1882(2) 0.0439(8) Uani 1 1 d . . . . .
N5 N 0.9502(5) 0.35442(17) 0.1243(2) 0.0683(10) Uani 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 N2 1.783(3) . ?
Se1 N1 1.800(3) . ?
K1 O6 2.804(2) . ?
K1 O5 2.794(2) . ?
K1 O4 2.798(2) . ?
K1 O3 2.799(2) . ?
K1 O2 2.784(2) . ?
K1 O1 2.817(2) . ?
K1 N6 2.996(3) . ?
K1 N1 3.072(3) 2_645 ?
N4 C2 1.373(4) . ?
N4 C3 1.314(4) . ?
N3 C4 1.303(4) . ?
N3 C1 1.365(4) . ?
O6 C7 1.425(4) . ?
O6 C18 1.423(4) . ?
O5 C8 1.423(4) . ?
O5 C9 1.422(4) . ?
O4 C10 1.418(4) . ?
O4 C11 1.420(4) . ?
O3 C12 1.423(4) . ?
O3 C13 1.438(4) . ?
O2 C14 1.437(4) . ?
O2 C15 1.417(4) . ?
O1 C16 1.417(4) . ?
O1 C17 1.422(4) . ?
N2 C2 1.328(4) . ?
C2 C1 1.440(4) . ?
C3 C6 1.450(5) . ?
C3 C4 1.444(4) . ?
C6 N6 1.133(4) . ?
N1 C1 1.326(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.490(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.492(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.482(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.478(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.497(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.488(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C4 C5 1.454(5) . ?
C5 N5 1.131(4) . ?

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 95.34(12) . . ?
O6 K1 O1 60.32(7) . . ?
O6 K1 N6 76.10(8) . . ?
O6 K1 N1 119.69(8) . 2_645 ?
O5 K1 O6 61.00(7) . . ?
O5 K1 O4 59.17(7) . . ?
O5 K1 O3 118.32(7) . . ?
O5 K1 O1 119.82(7) . . ?
O5 K1 N6 76.27(8) . . ?
O5 K1 N1 104.02(7) . 2_645 ?
O4 K1 O6 117.82(7) . . ?
O4 K1 O3 59.71(7) . . ?
O4 K1 O1 176.60(8) . . ?
O4 K1 N6 75.12(8) . . ?
O4 K1 N1 89.95(7) . 2_645 ?
O3 K1 O6 171.86(7) . . ?
O3 K1 O1 121.68(7) . . ?
O3 K1 N6 95.80(8) . . ?
O3 K1 N1 68.44(7) . 2_645 ?
O2 K1 O6 118.36(7) . . ?
O2 K1 O5 175.20(7) . . ?
O2 K1 O4 119.76(7) . . ?
O2 K1 O3 61.54(7) . . ?
O2 K1 O1 60.94(7) . . ?
O2 K1 N6 98.93(8) . . ?
O2 K1 N1 80.49(7) . 2_645 ?
O1 K1 N6 101.52(8) . . ?
O1 K1 N1 93.46(7) . 2_645 ?
N6 K1 N1 162.56(8) . 2_645 ?
C3 N4 C2 114.2(3) . . ?
C4 N3 C1 114.3(3) . . ?
C7 O6 K1 112.04(19) . . ?
C18 O6 K1 115.0(2) . . ?
C18 O6 C7 111.9(3) . . ?
C8 O5 K1 114.79(19) . . ?
C9 O5 K1 117.91(19) . . ?
C9 O5 C8 112.2(3) . . ?
C10 O4 K1 115.52(19) . . ?
C10 O4 C11 112.6(3) . . ?
C11 O4 K1 117.5(2) . . ?
C12 O3 K1 114.17(19) . . ?
C12 O3 C13 111.7(3) . . ?
C13 O3 K1 112.62(18) . . ?
C14 O2 K1 113.54(19) . . ?
C15 O2 K1 112.5(2) . . ?
C15 O2 C14 112.6(3) . . ?
C16 O1 K1 113.5(2) . . ?
C16 O1 C17 112.2(3) . . ?
C17 O1 K1 113.9(2) . . ?
C2 N2 Se1 105.1(2) . . ?
N4 C2 C1 122.1(3) . . ?
N2 C2 N4 120.4(3) . . ?
N2 C2 C1 117.6(3) . . ?
N4 C3 C6 117.9(3) . . ?
N4 C3 C4 123.0(3) . . ?
C4 C3 C6 119.0(3) . . ?
N6 C6 C3 175.9(3) . . ?
C6 N6 K1 144.7(3) . . ?
Se1 N1 K1 113.34(12) . 2_655 ?
C1 N1 Se1 105.2(2) . . ?
C1 N1 K1 141.4(2) . 2_655 ?
O6 C7 H7A 109.8 . . ?
O6 C7 H7B 109.8 . . ?
O6 C7 C8 109.4(3) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
O5 C8 C7 108.7(3) . . ?
O5 C8 H8A 109.9 . . ?
O5 C8 H8B 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O5 C9 H9A 110.0 . . ?
O5 C9 H9B 110.0 . . ?
O5 C9 C10 108.6(3) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
O4 C10 C9 108.2(3) . . ?
O4 C10 H10A 110.1 . . ?
O4 C10 H10B 110.1 . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
O4 C11 H11A 110.0 . . ?
O4 C11 H11B 110.0 . . ?
O4 C11 C12 108.4(3) . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
O3 C12 C11 109.8(3) . . ?
O3 C12 H12A 109.7 . . ?
O3 C12 H12B 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O3 C13 H13A 109.7 . . ?
O3 C13 H13B 109.7 . . ?
O3 C13 C14 110.0(3) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
O2 C14 C13 108.9(3) . . ?
O2 C14 H14A 109.9 . . ?
O2 C14 H14B 109.9 . . ?
C13 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O2 C15 H15A 110.1 . . ?
O2 C15 H15B 110.1 . . ?
O2 C15 C16 107.9(3) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
O1 C16 C15 109.7(3) . . ?
O1 C16 H16A 109.7 . . ?
O1 C16 H16B 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
O1 C17 H17A 109.8 . . ?
O1 C17 H17B 109.8 . . ?
O1 C17 C18 109.3(3) . . ?
H17A C17 H17B 108.3 . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
O6 C18 C17 109.0(3) . . ?
O6 C18 H18A 109.9 . . ?
O6 C18 H18B 109.9 . . ?
C17 C18 H18A 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
N3 C4 C3 124.3(3) . . ?
N3 C4 C5 117.5(3) . . ?
C3 C4 C5 118.2(3) . . ?
N3 C1 C2 122.1(3) . . ?
N1 C1 N3 121.2(3) . . ?
N1 C1 C2 116.6(3) . . ?
N5 C5 C4 176.6(4) . . ?

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 N2 C2 N4 -175.9(2) . . . . ?
Se1 N2 C2 C1 2.4(3) . . . . ?
Se1 N1 C1 N3 178.0(2) . . . . ?
Se1 N1 C1 C2 -1.3(3) . . . . ?
K1 O6 C7 C8 -53.0(3) . . . . ?
K1 O6 C18 C17 47.8(4) . . . . ?
K1 O5 C8 C7 -46.0(3) . . . . ?
K1 O5 C9 C10 42.9(3) . . . . ?
K1 O4 C10 C9 52.3(3) . . . . ?
K1 O4 C11 C12 -42.9(3) . . . . ?
K1 O3 C12 C11 -52.0(3) . . . . ?
K1 O3 C13 C14 49.0(3) . . . . ?
K1 O2 C14 C13 49.5(3) . . . . ?
K1 O2 C15 C16 -55.3(3) . . . . ?
K1 O1 C16 C15 -44.9(3) . . . . ?
K1 O1 C17 C18 49.8(4) . . . . ?
K1 N1 C1 N3 -3.2(5) 2_655 . . . ?
K1 N1 C1 C2 177.4(2) 2_655 . . . ?
N4 C2 C1 N3 -1.8(4) . . . . ?
N4 C2 C1 N1 177.5(3) . . . . ?
N4 C3 C4 N3 -1.8(5) . . . . ?
N4 C3 C4 C5 -178.3(3) . . . . ?
O6 C7 C8 O5 67.1(4) . . . . ?
O5 C9 C10 O4 -61.9(4) . . . . ?
O4 C11 C12 O3 62.5(4) . . . . ?
O3 C13 C14 O2 -66.9(4) . . . . ?
O2 C15 C16 O1 68.2(4) . . . . ?
O1 C17 C18 O6 -65.5(4) . . . . ?
N2 Se1 N1 K1 -176.88(12) . . . 2_655 ?
N2 Se1 N1 C1 2.3(2) . . . . ?
N2 C2 C1 N3 179.9(3) . . . . ?
N2 C2 C1 N1 -0.8(4) . . . . ?
C2 N4 C3 C6 -175.8(3) . . . . ?
C2 N4 C3 C4 1.6(4) . . . . ?
C3 N4 C2 N2 178.4(3) . . . . ?
C3 N4 C2 C1 0.1(4) . . . . ?
C6 C3 C4 N3 175.5(3) . . . . ?
C6 C3 C4 C5 -1.0(4) . . . . ?
N1 Se1 N2 C2 -2.6(2) . . . . ?
C7 O6 C18 C17 177.1(3) . . . . ?
C8 O5 C9 C10 179.7(3) . . . . ?
C9 O5 C8 C7 175.8(3) . . . . ?
C10 O4 C11 C12 179.2(3) . . . . ?
C11 O4 C10 C9 -168.9(3) . . . . ?
C12 O3 C13 C14 179.0(3) . . . . ?
C13 O3 C12 C11 178.8(3) . . . . ?
C14 O2 C15 C16 174.9(3) . . . . ?
C15 O2 C14 C13 178.8(3) . . . . ?
C16 O1 C17 C18 -179.5(3) . . . . ?
C17 O1 C16 C15 -175.7(3) . . . . ?
C18 O6 C7 C8 176.2(3) . . . . ?
C4 N3 C1 C2 1.6(4) . . . . ?
C4 N3 C1 N1 -177.7(3) . . . . ?
C1 N3 C4 C3 0.1(4) . . . . ?
C1 N3 C4 C5 176.6(3) . . . . ?

####################################################################### 
# 
# 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_4-Cl_Et4N
_database_code_depnum_ccdc_archive 'CCDC 2168143'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Radiush'
;Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-04-22 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-22
_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            
;
tetraethilammonium 1-chloro-(5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide)4
;
_chemical_name_systematic        
;
tetraethilammonium 1-chloro-(5,6-dicyano[1,2,5]selenadiazolo[3,4-b]pyrazolide)4
;
_chemical_formula_moiety         '2(C6 N6 Se), Cl, C8 H20 N'
_chemical_formula_sum            'C20 H20 Cl N13 Se2'
_chemical_formula_weight         635.86
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8914(9)
_cell_length_b                   12.6394(10)
_cell_length_c                   22.800(2)
_cell_angle_alpha                92.513(3)
_cell_angle_beta                 94.141(3)
_cell_angle_gamma                111.522(3)
_cell_volume                     2637.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.58
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.867
_shelx_estimated_absorpt_T_min   0.757
_exptl_absorpt_coefficient_mu    2.942
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5816
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0989 before and 0.0785 after correction.
The Ratio of minimum to maximum transmission is 0.7803.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.808
_diffrn_reflns_theta_min         2.015
_diffrn_ambient_temperature      200.04
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8039
_reflns_number_total             11155
_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 V8.18C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         11155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.000
_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)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1007
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C01C(H01A,H01B), C01G(H01C,H01D), C01K(H01E,H01F), C01L(H01G,H01H), C01R(H01U,
 H01V), C01T(H01W,H01X), C01V(H01Y,H), C01W(H01Z,HA)
2.b Idealised Me refined as rotating group:
 C01N(H01I,H01J,H01K), C01P(H01L,H01M,H01N), C01S(H01O,H01P,H01Q), C01U(H01R,
 H01S,H01T), C01X(H01,HB,HC), C01Y(H1,HD,HE), C01Z(H2,HF,HG), C020(H02A,H02B,
 H02C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.037
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se -0.26669(3) 0.25413(3) 0.87344(2) 0.02651(9) Uani 1 1 d . . . . .
Se02 Se 0.49373(3) 0.87370(3) 0.96413(2) 0.02862(9) Uani 1 1 d . . . . .
Se03 Se 0.60614(4) 0.58183(3) 0.93298(2) 0.03377(10) Uani 1 1 d . . . . .
Se04 Se 0.09505(4) 0.63267(3) 0.95527(2) 0.03531(10) Uani 1 1 d . . . . .
Cl Cl -0.22023(9) 0.13052(7) 0.97354(4) 0.03045(18) Uani 1 1 d . . . . .
Cl1 Cl 0.59599(10) 0.35710(8) 0.97274(4) 0.0433(2) Uani 1 1 d . . . . .
N007 N 0.6375(3) 0.8189(2) 0.81983(12) 0.0277(6) Uani 1 1 d . . . . .
N008 N -0.2014(3) 0.1194(2) 0.72973(12) 0.0284(6) Uani 1 1 d . . . . .
N009 N 0.4562(3) 0.9514(2) 0.80612(12) 0.0272(6) Uani 1 1 d . . . . .
N00A N 0.5271(3) 0.5215(2) 0.76720(12) 0.0302(6) Uani 1 1 d . . . . .
N00B N -0.2287(3) 0.1501(2) 0.82952(11) 0.0235(6) Uani 1 1 d . . . . .
N00C N 0.8351(3) 0.6110(2) 0.80388(13) 0.0323(6) Uani 1 1 d . . . . .
N00D N 0.1419(3) 0.0901(2) 0.86420(12) 0.0262(6) Uani 1 1 d . . . . .
N00E N 0.4378(3) 0.9452(2) 0.90762(12) 0.0283(6) Uani 1 1 d . . . . .
N00F N 0.2424(3) 0.6716(2) 0.80502(12) 0.0340(7) Uani 1 1 d . . . . .
N00G N 0.0887(3) 0.4342(2) 0.82278(13) 0.0322(6) Uani 1 1 d . . . . .
N00H N -0.2840(3) 0.3352(2) 0.81245(12) 0.0299(6) Uani 1 1 d . . . . .
N00I N 0.5946(3) 0.8164(2) 0.91984(11) 0.0271(6) Uani 1 1 d . . . . .
N00J N -0.2627(3) 0.3212(2) 0.71015(13) 0.0374(7) Uani 1 1 d . . . . .
N00K N 0.4899(3) 0.5387(2) 0.86717(13) 0.0330(7) Uani 1 1 d . . . . .
N00L N 0.7722(3) 0.6173(2) 0.90070(12) 0.0328(6) Uani 1 1 d . . . . .
C00M C 0.6052(3) 0.8540(3) 0.76858(15) 0.0281(7) Uani 1 1 d . . . . .
N00N N 0.1849(3) 0.7129(2) 0.89889(13) 0.0349(7) Uani 1 1 d . . . . .
N00O N 0.0482(3) 0.4974(2) 0.91628(13) 0.0358(7) Uani 1 1 d . . . . .
C00P C 0.5771(3) 0.8496(2) 0.86604(14) 0.0232(7) Uani 1 1 d . . . . .
C00Q C -0.2054(4) 0.1590(3) 0.67808(14) 0.0307(7) Uani 1 1 d . . . . .
N00R N -0.2229(4) 0.7373(3) 0.49677(13) 0.0470(8) Uani 1 1 d . . . . .
N00S N 0.7331(4) 0.8066(3) 0.68189(15) 0.0509(9) Uani 1 1 d . . . . .
C00T C 0.6737(4) 0.8280(3) 0.71980(16) 0.0342(8) Uani 1 1 d . . . . .
C00U C -0.2289(3) 0.1810(2) 0.77453(13) 0.0224(7) Uani 1 1 d . . . . .
C00V C -0.2593(3) 0.2825(3) 0.76494(14) 0.0258(7) Uani 1 1 d . . . . .
C00W C 0.7807(4) 0.5821(3) 0.74860(15) 0.0326(8) Uani 1 1 d . . . . .
C00X C 0.5123(3) 0.9165(3) 0.76192(15) 0.0285(7) Uani 1 1 d . . . . .
C00Y C 0.4889(3) 0.9183(2) 0.85930(14) 0.0250(7) Uani 1 1 d . . . . .
C00Z C -0.2353(4) 0.2598(3) 0.66847(15) 0.0341(8) Uani 1 1 d . . . . .
C010 C 0.6284(4) 0.5376(3) 0.73051(15) 0.0323(8) Uani 1 1 d . . . . .
C011 C 0.2267(4) 0.5875(3) 0.76531(15) 0.0334(8) Uani 1 1 d . . . . .
C012 C 0.5791(3) 0.5498(2) 0.82432(15) 0.0270(7) Uani 1 1 d . . . . .
C013 C 0.7344(4) 0.5940(3) 0.84299(15) 0.0282(7) Uani 1 1 d . . . . .
N014 N 0.3398(4) 0.6429(3) 0.66707(16) 0.0579(9) Uani 1 1 d . . . . .
C015 C 0.1791(4) 0.6370(3) 0.85530(15) 0.0303(7) Uani 1 1 d . . . . .
N016 N 0.1212(4) 0.3170(3) 0.69041(16) 0.0572(9) Uani 1 1 d . . . . .
C017 C -0.1746(4) 0.0984(3) 0.62843(17) 0.0411(9) Uani 1 1 d . . . . .
N018 N -0.1495(4) 0.0523(3) 0.58955(15) 0.0618(10) Uani 1 1 d . . . . .
C019 C 0.5813(4) 0.5063(3) 0.66843(18) 0.0405(9) Uani 1 1 d . . . . .
C01A C 0.1501(3) 0.4703(3) 0.77409(16) 0.0315(8) Uani 1 1 d . . . . .
C01B C 0.2903(4) 0.6184(3) 0.71042(17) 0.0377(8) Uani 1 1 d . . . . .
C01C C 0.3019(3) 0.1448(3) 0.85348(16) 0.0325(8) Uani 1 1 d . . . . .
H01A H 0.359891 0.177748 0.891634 0.039 Uiso 1 1 calc R U . . .
H01B H 0.334865 0.084795 0.837985 0.039 Uiso 1 1 calc R U . . .
C01D C 0.1044(3) 0.5189(3) 0.86493(15) 0.0296(7) Uani 1 1 d . . . . .
C01E C 0.1358(4) 0.3847(3) 0.72775(17) 0.0399(9) Uani 1 1 d . . . . .
C01F C 0.4781(4) 0.9484(3) 0.70407(17) 0.0393(9) Uani 1 1 d . . . . .
C01G C 0.0867(4) 0.1789(3) 0.88816(15) 0.0320(8) Uani 1 1 d . . . . .
H01C H 0.080757 0.228053 0.856199 0.038 Uiso 1 1 calc R U . . .
H01D H -0.013586 0.139355 0.899177 0.038 Uiso 1 1 calc R U . . .
N01H N 0.5463(4) 0.4812(3) 0.61910(16) 0.0606(10) Uani 1 1 d . . . . .
N01I N 0.4526(4) 0.9747(3) 0.65839(17) 0.0659(11) Uani 1 1 d . . . . .
N01J N 0.9613(4) 0.6048(4) 0.66857(18) 0.0740(12) Uani 1 1 d . . . . .
C01K C 0.0481(4) 0.0356(3) 0.80782(16) 0.0403(9) Uani 1 1 d . . . . .
H01E H 0.058677 0.095300 0.779862 0.048 Uiso 1 1 calc R U . . .
H01F H -0.055284 0.004564 0.816440 0.048 Uiso 1 1 calc R U . . .
C01L C 0.1316(4) 0.0021(3) 0.90891(17) 0.0372(9) Uani 1 1 d . . . . .
H01G H 0.180033 -0.048797 0.894564 0.045 Uiso 1 1 calc R U . . .
H01H H 0.186315 0.042293 0.946540 0.045 Uiso 1 1 calc R U . . .
C01M C 0.8826(4) 0.5957(4) 0.70445(18) 0.0469(10) Uani 1 1 d . . . . .
C01N C 0.3330(4) 0.2376(3) 0.81071(18) 0.0478(10) Uani 1 1 d . . . . .
H01I H 0.279848 0.205049 0.772180 0.072 Uiso 1 1 calc R U . . .
H01J H 0.438007 0.269978 0.806602 0.072 Uiso 1 1 calc R U . . .
H01K H 0.301271 0.297679 0.825719 0.072 Uiso 1 1 calc R U . . .
C01O C -0.2347(5) 0.2973(4) 0.60907(18) 0.0543(11) Uani 1 1 d . . . . .
C01P C -0.0224(4) -0.0706(3) 0.92092(19) 0.0470(10) Uani 1 1 d . . . . .
H01L H -0.076063 -0.114654 0.884504 0.070 Uiso 1 1 calc R U . . .
H01M H -0.071851 -0.021256 0.935048 0.070 Uiso 1 1 calc R U . . .
H01N H -0.018941 -0.122838 0.950993 0.070 Uiso 1 1 calc R U . . .
N01Q N -0.2308(6) 0.3225(4) 0.56170(17) 0.0879(15) Uani 1 1 d . . . . .
C01R C -0.1282(5) 0.7670(4) 0.55456(18) 0.0584(11) Uani 1 1 d . . . . .
H01U H -0.156749 0.698768 0.577520 0.070 Uiso 1 1 calc R U . . .
H01V H -0.149060 0.827091 0.577142 0.070 Uiso 1 1 calc R U . . .
C01S C 0.0839(5) -0.0589(4) 0.7783(2) 0.0710(14) Uani 1 1 d . . . . .
H01O H 0.018387 -0.089815 0.742177 0.107 Uiso 1 1 calc R U . . .
H01P H 0.071147 -0.119643 0.805172 0.107 Uiso 1 1 calc R U . . .
H01Q H 0.185224 -0.028767 0.768503 0.107 Uiso 1 1 calc R U . . .
C01T C -0.1965(5) 0.8454(3) 0.46533(19) 0.0569(11) Uani 1 1 d . . . . .
H01W H -0.212633 0.902176 0.492367 0.068 Uiso 1 1 calc R U . . .
H01X H -0.092859 0.876787 0.457073 0.068 Uiso 1 1 calc R U . . .
C01U C 0.1783(4) 0.2545(3) 0.94104(18) 0.0486(10) Uani 1 1 d . . . . .
H01R H 0.273801 0.302340 0.929369 0.073 Uiso 1 1 calc R U . . .
H01S H 0.191466 0.206947 0.972054 0.073 Uiso 1 1 calc R U . . .
H01T H 0.128788 0.303245 0.955925 0.073 Uiso 1 1 calc R U . . .
C01V C -0.3832(5) 0.6865(4) 0.5106(2) 0.0677(13) Uani 1 1 d . . . . .
H01Y H -0.444806 0.653926 0.473149 0.081 Uiso 1 1 calc R U . . .
H H -0.394288 0.622679 0.535921 0.081 Uiso 1 1 calc R U . . .
C01W C -0.1876(6) 0.6547(4) 0.45745(19) 0.0634(12) Uani 1 1 d . . . . .
H01Z H -0.087961 0.693102 0.445513 0.076 Uiso 1 1 calc R U . . .
HA H -0.256232 0.634247 0.421266 0.076 Uiso 1 1 calc R U . . .
C01X C -0.2900(6) 0.8318(4) 0.4085(2) 0.0799(16) Uani 1 1 d . . . . .
H01 H -0.271438 0.778913 0.380440 0.120 Uiso 1 1 calc R U . . .
HB H -0.266530 0.906117 0.392066 0.120 Uiso 1 1 calc R U . . .
HC H -0.393163 0.801516 0.415983 0.120 Uiso 1 1 calc R U . . .
C01Y C -0.4409(6) 0.7666(5) 0.5404(2) 0.0844(17) Uani 1 1 d . . . . .
H1 H -0.437715 0.827344 0.514589 0.127 Uiso 1 1 calc R U . . .
HD H -0.380848 0.800093 0.577493 0.127 Uiso 1 1 calc R U . . .
HE H -0.541945 0.724889 0.548501 0.127 Uiso 1 1 calc R U . . .
C01Z C 0.0348(5) 0.8081(5) 0.5500(2) 0.0748(14) Uani 1 1 d . . . . .
H2 H 0.063706 0.871686 0.524545 0.112 Uiso 1 1 calc R U . . .
HF H 0.059336 0.745492 0.533029 0.112 Uiso 1 1 calc R U . . .
HG H 0.086862 0.833513 0.589318 0.112 Uiso 1 1 calc R U . . .
C020 C -0.1952(7) 0.5461(4) 0.4850(3) 0.0950(19) Uani 1 1 d . . . . .
H02A H -0.182897 0.493072 0.455139 0.143 Uiso 1 1 calc R U . . .
H02B H -0.290234 0.511006 0.500463 0.143 Uiso 1 1 calc R U . . .
H02C H -0.117393 0.564066 0.517268 0.143 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 N00B 1.781(2) . ?
Se01 N00H 1.798(3) . ?
Se02 N00E 1.774(3) . ?
Se02 N00I 1.775(2) . ?
Se03 N00K 1.758(3) . ?
Se03 N00L 1.762(3) . ?
Se04 N00N 1.758(3) . ?
Se04 N00O 1.776(3) . ?
N007 C00M 1.326(4) . ?
N007 C00P 1.357(4) . ?
N008 C00Q 1.303(4) . ?
N008 C00U 1.360(4) . ?
N009 C00X 1.319(4) . ?
N009 C00Y 1.356(4) . ?
N00A C010 1.316(4) . ?
N00A C012 1.348(4) . ?
N00B C00U 1.329(4) . ?
N00C C00W 1.315(4) . ?
N00C C013 1.350(4) . ?
N00D C01C 1.520(4) . ?
N00D C01G 1.516(4) . ?
N00D C01K 1.506(4) . ?
N00D C01L 1.522(4) . ?
N00E C00Y 1.326(4) . ?
N00F C011 1.323(4) . ?
N00F C015 1.358(4) . ?
N00G C01A 1.322(4) . ?
N00G C01D 1.364(4) . ?
N00H C00V 1.331(4) . ?
N00I C00P 1.334(4) . ?
N00J C00V 1.364(4) . ?
N00J C00Z 1.306(4) . ?
N00K C012 1.341(4) . ?
N00L C013 1.331(4) . ?
C00M C00T 1.430(5) . ?
C00M C00X 1.420(4) . ?
N00N C015 1.334(4) . ?
N00O C01D 1.328(4) . ?
C00P C00Y 1.443(4) . ?
C00Q C00Z 1.432(4) . ?
C00Q C017 1.452(5) . ?
N00R C01R 1.508(5) . ?
N00R C01T 1.516(5) . ?
N00R C01V 1.539(6) . ?
N00R C01W 1.500(5) . ?
N00S C00T 1.155(4) . ?
C00U C00V 1.443(4) . ?
C00W C010 1.422(5) . ?
C00W C01M 1.447(5) . ?
C00X C01F 1.449(5) . ?
C00Z C01O 1.454(5) . ?
C010 C019 1.448(5) . ?
C011 C01A 1.425(5) . ?
C011 C01B 1.446(5) . ?
C012 C013 1.451(4) . ?
N014 C01B 1.139(5) . ?
C015 C01D 1.436(4) . ?
N016 C01E 1.143(5) . ?
C017 N018 1.131(5) . ?
C019 N01H 1.148(5) . ?
C01A C01E 1.439(5) . ?
C01C H01A 0.9900 . ?
C01C H01B 0.9900 . ?
C01C C01N 1.517(5) . ?
C01F N01I 1.146(5) . ?
C01G H01C 0.9900 . ?
C01G H01D 0.9900 . ?
C01G C01U 1.514(5) . ?
N01J C01M 1.150(5) . ?
C01K H01E 0.9900 . ?
C01K H01F 0.9900 . ?
C01K C01S 1.510(5) . ?
C01L H01G 0.9900 . ?
C01L H01H 0.9900 . ?
C01L C01P 1.515(5) . ?
C01N H01I 0.9800 . ?
C01N H01J 0.9800 . ?
C01N H01K 0.9800 . ?
C01O N01Q 1.139(5) . ?
C01P H01L 0.9800 . ?
C01P H01M 0.9800 . ?
C01P H01N 0.9800 . ?
C01R H01U 0.9900 . ?
C01R H01V 0.9900 . ?
C01R C01Z 1.515(6) . ?
C01S H01O 0.9800 . ?
C01S H01P 0.9800 . ?
C01S H01Q 0.9800 . ?
C01T H01W 0.9900 . ?
C01T H01X 0.9900 . ?
C01T C01X 1.501(6) . ?
C01U H01R 0.9800 . ?
C01U H01S 0.9800 . ?
C01U H01T 0.9800 . ?
C01V H01Y 0.9900 . ?
C01V H 0.9900 . ?
C01V C01Y 1.494(7) . ?
C01W H01Z 0.9900 . ?
C01W HA 0.9900 . ?
C01W C020 1.513(6) . ?
C01X H01 0.9800 . ?
C01X HB 0.9800 . ?
C01X HC 0.9800 . ?
C01Y H1 0.9800 . ?
C01Y HD 0.9800 . ?
C01Y HE 0.9800 . ?
C01Z H2 0.9800 . ?
C01Z HF 0.9800 . ?
C01Z HG 0.9800 . ?
C020 H02A 0.9800 . ?
C020 H02B 0.9800 . ?
C020 H02C 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
N00B Se01 N00H 94.50(11) . . ?
N00E Se02 N00I 96.03(12) . . ?
N00K Se03 N00L 97.10(13) . . ?
N00N Se04 N00O 95.82(13) . . ?
C00M N007 C00P 114.7(3) . . ?
C00Q N008 C00U 114.8(3) . . ?
C00X N009 C00Y 114.5(3) . . ?
C010 N00A C012 114.4(3) . . ?
C00U N00B Se01 106.35(18) . . ?
C00W N00C C013 114.6(3) . . ?
C01C N00D C01L 106.8(2) . . ?
C01G N00D C01C 110.6(2) . . ?
C01G N00D C01L 110.2(2) . . ?
C01K N00D C01C 111.3(3) . . ?
C01K N00D C01G 106.8(2) . . ?
C01K N00D C01L 111.2(3) . . ?
C00Y N00E Se02 105.38(19) . . ?
C011 N00F C015 114.2(3) . . ?
C01A N00G C01D 114.4(3) . . ?
C00V N00H Se01 106.23(19) . . ?
C00P N00I Se02 105.12(19) . . ?
C00Z N00J C00V 114.5(3) . . ?
C012 N00K Se03 105.0(2) . . ?
C013 N00L Se03 105.1(2) . . ?
N007 C00M C00T 115.8(3) . . ?
N007 C00M C00X 123.0(3) . . ?
C00X C00M C00T 121.2(3) . . ?
C015 N00N Se04 105.7(2) . . ?
C01D N00O Se04 105.5(2) . . ?
N007 C00P C00Y 121.8(3) . . ?
N00I C00P N007 121.6(3) . . ?
N00I C00P C00Y 116.6(3) . . ?
N008 C00Q C00Z 123.3(3) . . ?
N008 C00Q C017 117.7(3) . . ?
C00Z C00Q C017 119.0(3) . . ?
C01R N00R C01T 108.8(3) . . ?
C01R N00R C01V 107.8(3) . . ?
C01T N00R C01V 109.8(3) . . ?
C01W N00R C01R 111.6(3) . . ?
C01W N00R C01T 108.3(3) . . ?
C01W N00R C01V 110.6(3) . . ?
N00S C00T C00M 177.4(4) . . ?
N008 C00U C00V 122.0(3) . . ?
N00B C00U N008 121.2(2) . . ?
N00B C00U C00V 116.8(3) . . ?
N00H C00V N00J 122.4(3) . . ?
N00H C00V C00U 116.1(3) . . ?
N00J C00V C00U 121.5(3) . . ?
N00C C00W C010 123.5(3) . . ?
N00C C00W C01M 117.5(3) . . ?
C010 C00W C01M 119.0(3) . . ?
N009 C00X C00M 123.9(3) . . ?
N009 C00X C01F 116.4(3) . . ?
C00M C00X C01F 119.7(3) . . ?
N009 C00Y C00P 122.0(3) . . ?
N00E C00Y N009 121.2(3) . . ?
N00E C00Y C00P 116.7(3) . . ?
N00J C00Z C00Q 123.9(3) . . ?
N00J C00Z C01O 117.5(3) . . ?
C00Q C00Z C01O 118.6(3) . . ?
N00A C010 C00W 123.7(3) . . ?
N00A C010 C019 117.8(3) . . ?
C00W C010 C019 118.5(3) . . ?
N00F C011 C01A 123.3(3) . . ?
N00F C011 C01B 117.1(3) . . ?
C01A C011 C01B 119.6(3) . . ?
N00A C012 C013 122.1(3) . . ?
N00K C012 N00A 121.7(3) . . ?
N00K C012 C013 116.2(3) . . ?
N00C C013 C012 121.8(3) . . ?
N00L C013 N00C 121.7(3) . . ?
N00L C013 C012 116.5(3) . . ?
N00F C015 C01D 122.8(3) . . ?
N00N C015 N00F 120.6(3) . . ?
N00N C015 C01D 116.6(3) . . ?
N018 C017 C00Q 179.2(4) . . ?
N01H C019 C010 178.8(4) . . ?
N00G C01A C011 123.7(3) . . ?
N00G C01A C01E 116.9(3) . . ?
C011 C01A C01E 119.3(3) . . ?
N014 C01B C011 179.6(4) . . ?
N00D C01C H01A 108.8 . . ?
N00D C01C H01B 108.8 . . ?
H01A C01C H01B 107.7 . . ?
C01N C01C N00D 114.0(3) . . ?
C01N C01C H01A 108.8 . . ?
C01N C01C H01B 108.8 . . ?
N00G C01D C015 121.5(3) . . ?
N00O C01D N00G 122.1(3) . . ?
N00O C01D C015 116.3(3) . . ?
N016 C01E C01A 178.2(4) . . ?
N01I C01F C00X 179.2(5) . . ?
N00D C01G H01C 108.4 . . ?
N00D C01G H01D 108.4 . . ?
H01C C01G H01D 107.5 . . ?
C01U C01G N00D 115.4(3) . . ?
C01U C01G H01C 108.4 . . ?
C01U C01G H01D 108.4 . . ?
N00D C01K H01E 108.6 . . ?
N00D C01K H01F 108.6 . . ?
N00D C01K C01S 114.5(3) . . ?
H01E C01K H01F 107.6 . . ?
C01S C01K H01E 108.6 . . ?
C01S C01K H01F 108.6 . . ?
N00D C01L H01G 108.6 . . ?
N00D C01L H01H 108.6 . . ?
H01G C01L H01H 107.5 . . ?
C01P C01L N00D 114.8(3) . . ?
C01P C01L H01G 108.6 . . ?
C01P C01L H01H 108.6 . . ?
N01J C01M C00W 178.5(5) . . ?
C01C C01N H01I 109.5 . . ?
C01C C01N H01J 109.5 . . ?
C01C C01N H01K 109.5 . . ?
H01I C01N H01J 109.5 . . ?
H01I C01N H01K 109.5 . . ?
H01J C01N H01K 109.5 . . ?
N01Q C01O C00Z 176.3(4) . . ?
C01L C01P H01L 109.5 . . ?
C01L C01P H01M 109.5 . . ?
C01L C01P H01N 109.5 . . ?
H01L C01P H01M 109.5 . . ?
H01L C01P H01N 109.5 . . ?
H01M C01P H01N 109.5 . . ?
N00R C01R H01U 108.3 . . ?
N00R C01R H01V 108.3 . . ?
N00R C01R C01Z 115.7(4) . . ?
H01U C01R H01V 107.4 . . ?
C01Z C01R H01U 108.3 . . ?
C01Z C01R H01V 108.3 . . ?
C01K C01S H01O 109.5 . . ?
C01K C01S H01P 109.5 . . ?
C01K C01S H01Q 109.5 . . ?
H01O C01S H01P 109.5 . . ?
H01O C01S H01Q 109.5 . . ?
H01P C01S H01Q 109.5 . . ?
N00R C01T H01W 108.4 . . ?
N00R C01T H01X 108.4 . . ?
H01W C01T H01X 107.5 . . ?
C01X C01T N00R 115.5(4) . . ?
C01X C01T H01W 108.4 . . ?
C01X C01T H01X 108.4 . . ?
C01G C01U H01R 109.5 . . ?
C01G C01U H01S 109.5 . . ?
C01G C01U H01T 109.5 . . ?
H01R C01U H01S 109.5 . . ?
H01R C01U H01T 109.5 . . ?
H01S C01U H01T 109.5 . . ?
N00R C01V H01Y 108.2 . . ?
N00R C01V H 108.2 . . ?
H01Y C01V H 107.4 . . ?
C01Y C01V N00R 116.3(4) . . ?
C01Y C01V H01Y 108.2 . . ?
C01Y C01V H 108.2 . . ?
N00R C01W H01Z 108.6 . . ?
N00R C01W HA 108.6 . . ?
N00R C01W C020 114.6(4) . . ?
H01Z C01W HA 107.6 . . ?
C020 C01W H01Z 108.6 . . ?
C020 C01W HA 108.6 . . ?
C01T C01X H01 109.5 . . ?
C01T C01X HB 109.5 . . ?
C01T C01X HC 109.5 . . ?
H01 C01X HB 109.5 . . ?
H01 C01X HC 109.5 . . ?
HB C01X HC 109.5 . . ?
C01V C01Y H1 109.5 . . ?
C01V C01Y HD 109.5 . . ?
C01V C01Y HE 109.5 . . ?
H1 C01Y HD 109.5 . . ?
H1 C01Y HE 109.5 . . ?
HD C01Y HE 109.5 . . ?
C01R C01Z H2 109.5 . . ?
C01R C01Z HF 109.5 . . ?
C01R C01Z HG 109.5 . . ?
H2 C01Z HF 109.5 . . ?
H2 C01Z HG 109.5 . . ?
HF C01Z HG 109.5 . . ?
C01W C020 H02A 109.5 . . ?
C01W C020 H02B 109.5 . . ?
C01W C020 H02C 109.5 . . ?
H02A C020 H02B 109.5 . . ?
H02A C020 H02C 109.5 . . ?
H02B C020 H02C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se01 N00B C00U N008 179.2(2) . . . . ?
Se01 N00B C00U C00V -0.7(3) . . . . ?
Se01 N00H C00V N00J -179.7(3) . . . . ?
Se01 N00H C00V C00U 0.6(3) . . . . ?
Se02 N00E C00Y N009 174.8(2) . . . . ?
Se02 N00E C00Y C00P -3.6(3) . . . . ?
Se02 N00I C00P N007 -178.6(2) . . . . ?
Se02 N00I C00P C00Y 0.4(3) . . . . ?
Se03 N00K C012 N00A 178.5(2) . . . . ?
Se03 N00K C012 C013 -1.7(3) . . . . ?
Se03 N00L C013 N00C 180.0(2) . . . . ?
Se03 N00L C013 C012 0.1(3) . . . . ?
Se04 N00N C015 N00F -178.6(2) . . . . ?
Se04 N00N C015 C01D 1.0(4) . . . . ?
Se04 N00O C01D N00G -179.4(2) . . . . ?
Se04 N00O C01D C015 -1.2(3) . . . . ?
N007 C00M C00X N009 4.1(5) . . . . ?
N007 C00M C00X C01F -177.8(3) . . . . ?
N007 C00P C00Y N009 3.0(5) . . . . ?
N007 C00P C00Y N00E -178.7(3) . . . . ?
N008 C00Q C00Z N00J -0.6(6) . . . . ?
N008 C00Q C00Z C01O 179.0(4) . . . . ?
N008 C00U C00V N00H -179.9(3) . . . . ?
N008 C00U C00V N00J 0.4(5) . . . . ?
N00A C012 C013 N00C 1.1(4) . . . . ?
N00A C012 C013 N00L -179.0(3) . . . . ?
N00B Se01 N00H C00V -0.8(2) . . . . ?
N00B C00U C00V N00H 0.1(4) . . . . ?
N00B C00U C00V N00J -179.7(3) . . . . ?
N00C C00W C010 N00A 0.3(5) . . . . ?
N00C C00W C010 C019 -178.5(3) . . . . ?
N00E Se02 N00I C00P -2.1(2) . . . . ?
N00F C011 C01A N00G -0.7(5) . . . . ?
N00F C011 C01A C01E 178.6(3) . . . . ?
N00F C015 C01D N00G -2.1(5) . . . . ?
N00F C015 C01D N00O 179.8(3) . . . . ?
N00H Se01 N00B C00U 0.9(2) . . . . ?
N00I Se02 N00E C00Y 3.3(2) . . . . ?
N00I C00P C00Y N009 -176.0(3) . . . . ?
N00I C00P C00Y N00E 2.3(4) . . . . ?
N00K Se03 N00L C013 -0.9(2) . . . . ?
N00K C012 C013 N00C -178.8(3) . . . . ?
N00K C012 C013 N00L 1.1(4) . . . . ?
N00L Se03 N00K C012 1.5(2) . . . . ?
C00M N007 C00P N00I 177.1(3) . . . . ?
C00M N007 C00P C00Y -1.9(4) . . . . ?
N00N Se04 N00O C01D 1.6(2) . . . . ?
N00N C015 C01D N00G 178.3(3) . . . . ?
N00N C015 C01D N00O 0.2(5) . . . . ?
N00O Se04 N00N C015 -1.5(2) . . . . ?
C00P N007 C00M C00T 176.8(3) . . . . ?
C00P N007 C00M C00X -1.4(4) . . . . ?
C00Q N008 C00U N00B 179.8(3) . . . . ?
C00Q N008 C00U C00V -0.2(4) . . . . ?
C00T C00M C00X N009 -173.9(3) . . . . ?
C00T C00M C00X C01F 4.1(5) . . . . ?
C00U N008 C00Q C00Z 0.3(5) . . . . ?
C00U N008 C00Q C017 179.0(3) . . . . ?
C00V N00J C00Z C00Q 0.7(5) . . . . ?
C00V N00J C00Z C01O -179.0(3) . . . . ?
C00W N00C C013 N00L 178.8(3) . . . . ?
C00W N00C C013 C012 -1.3(4) . . . . ?
C00X N009 C00Y N00E -178.7(3) . . . . ?
C00X N009 C00Y C00P -0.4(4) . . . . ?
C00Y N009 C00X C00M -2.9(4) . . . . ?
C00Y N009 C00X C01F 179.0(3) . . . . ?
C00Z N00J C00V N00H 179.7(3) . . . . ?
C00Z N00J C00V C00U -0.6(5) . . . . ?
C010 N00A C012 N00K 179.7(3) . . . . ?
C010 N00A C012 C013 -0.1(4) . . . . ?
C011 N00F C015 N00N -179.2(3) . . . . ?
C011 N00F C015 C01D 1.2(5) . . . . ?
C012 N00A C010 C00W -0.5(4) . . . . ?
C012 N00A C010 C019 178.3(3) . . . . ?
C013 N00C C00W C010 0.6(4) . . . . ?
C013 N00C C00W C01M -178.7(3) . . . . ?
C015 N00F C011 C01A 0.1(5) . . . . ?
C015 N00F C011 C01B 179.5(3) . . . . ?
C017 C00Q C00Z N00J -179.2(3) . . . . ?
C017 C00Q C00Z C01O 0.4(5) . . . . ?
C01A N00G C01D N00O 179.4(3) . . . . ?
C01A N00G C01D C015 1.4(4) . . . . ?
C01B C011 C01A N00G 179.9(3) . . . . ?
C01B C011 C01A C01E -0.8(5) . . . . ?
C01C N00D C01G C01U -51.4(4) . . . . ?
C01C N00D C01K C01S 61.2(4) . . . . ?
C01C N00D C01L C01P -174.1(3) . . . . ?
C01D N00G C01A C011 -0.1(5) . . . . ?
C01D N00G C01A C01E -179.4(3) . . . . ?
C01G N00D C01C C01N -58.6(4) . . . . ?
C01G N00D C01K C01S -178.0(3) . . . . ?
C01G N00D C01L C01P 65.6(4) . . . . ?
C01K N00D C01C C01N 59.9(4) . . . . ?
C01K N00D C01G C01U -172.7(3) . . . . ?
C01K N00D C01L C01P -52.5(4) . . . . ?
C01L N00D C01C C01N -178.6(3) . . . . ?
C01L N00D C01G C01U 66.5(4) . . . . ?
C01L N00D C01K C01S -57.8(4) . . . . ?
C01M C00W C010 N00A 179.6(3) . . . . ?
C01M C00W C010 C019 0.8(5) . . . . ?
C01R N00R C01T C01X -176.2(4) . . . . ?
C01R N00R C01V C01Y 68.2(5) . . . . ?
C01R N00R C01W C020 54.9(5) . . . . ?
C01T N00R C01R C01Z -66.7(5) . . . . ?
C01T N00R C01V C01Y -50.1(5) . . . . ?
C01T N00R C01W C020 174.6(4) . . . . ?
C01V N00R C01R C01Z 174.3(4) . . . . ?
C01V N00R C01T C01X -58.5(5) . . . . ?
C01V N00R C01W C020 -65.1(5) . . . . ?
C01W N00R C01R C01Z 52.7(5) . . . . ?
C01W N00R C01T C01X 62.4(5) . . . . ?
C01W N00R C01V C01Y -169.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

#==============================================================================
#     End of CIF
#==============================================================================


