# 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 2019

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1917743'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;NN Vorozhtsov Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;
_audit_creation_date             2016-09-21
_audit_creation_method           'by CrystalStructure 4.2'
_chemical_name_systematic        
;
 5,6-Dicyano[1,2,5]selenadiazolo[3,4-b]pyrazine 
;
_chemical_formula_sum            'C6 N6 Se'
_chemical_formula_moiety         'C6 N6 Se'
_chemical_formula_weight         235.07
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   18.847(5)
_cell_length_b                   10.756(3)
_cell_length_c                   7.0728(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1433.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2993
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    2.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896.00
_exptl_absorpt_coefficient_mu    5.188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_T_max  0.901

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            8956
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1314
_reflns_number_gt                1062
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0489
_refine_ls_wR_factor_gt          0.0481
_refine_ls_number_restraints     0
_refine_ls_number_reflns         1314
_refine_ls_number_parameters     118
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0266P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.0929 2.2259
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.41215(2) 0.37544(2) 0.19808(3) 0.01710(10) Uani 1 1 d . . . . .
N1 N 0.34695(10) 0.48275(17) 0.2792(3) 0.0164(4) Uani 1 1 d . . . . .
N2 N 0.35099(9) 0.27030(16) 0.0916(3) 0.0174(4) Uani 1 1 d . . . . .
N3 N 0.22678(10) 0.26237(15) 0.0568(2) 0.0147(4) Uani 1 1 d . . . . .
N8 N 0.04154(11) 0.54238(18) 0.2281(3) 0.0231(5) Uani 1 1 d . . . . .
N6 N 0.22236(9) 0.49648(16) 0.2605(3) 0.0138(4) Uani 1 1 d . . . . .
N7 N 0.04834(11) 0.23084(17) -0.0229(3) 0.0229(5) Uani 1 1 d . . . . .
C1 C 0.28462(12) 0.4356(2) 0.2248(3) 0.0145(5) Uani 1 1 d . . . . .
C2 C 0.28694(11) 0.31923(19) 0.1223(3) 0.0135(5) Uani 1 1 d . . . . .
C4 C 0.16815(11) 0.32331(19) 0.0939(3) 0.0140(5) Uani 1 1 d . . . . .
C5 C 0.16592(11) 0.4405(2) 0.1942(3) 0.0133(5) Uani 1 1 d . . . . .
C7 C 0.10187(13) 0.2699(2) 0.0280(3) 0.0159(5) Uani 1 1 d . . . . .
C8 C 0.09704(13) 0.4999(2) 0.2167(3) 0.0155(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.7809(19) . ?
Se1 N2 1.7817(18) . ?
N1 C1 1.336(3) . ?
N2 C2 1.335(3) . ?
N3 C4 1.311(3) . ?
N3 C2 1.369(3) . ?
N8 C8 1.145(3) . ?
N6 C5 1.309(3) . ?
N6 C1 1.367(3) . ?
N7 C7 1.151(3) . ?
C1 C2 1.447(3) . ?
C4 C7 1.452(3) . ?
C4 C5 1.447(3) . ?
C5 C8 1.455(3) . ?

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 95.81(9) . . ?
C1 N1 Se1 105.53(15) . . ?
C2 N2 Se1 105.44(15) . . ?
C4 N3 C2 114.02(17) . . ?
C5 N6 C1 114.28(18) . . ?
N1 C1 N6 121.3(2) . . ?
N1 C1 C2 116.49(19) . . ?
N6 C1 C2 122.18(19) . . ?
N2 C2 N3 121.20(19) . . ?
N2 C2 C1 116.72(19) . . ?
N3 C2 C1 122.07(19) . . ?
N3 C4 C7 117.61(19) . . ?
N3 C4 C5 123.91(19) . . ?
C7 C4 C5 118.48(19) . . ?
N6 C5 C4 123.54(19) . . ?
N6 C5 C8 118.9(2) . . ?
C4 C5 C8 117.49(19) . . ?
N7 C7 C4 178.0(2) . . ?
N8 C8 C5 176.6(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
N2 Se1 N1 C1 0.23(15) . . . . ?
N1 Se1 N2 C2 -0.28(15) . . . . ?
Se1 N1 C1 N6 -178.44(17) . . . . ?
Se1 N1 C1 C2 -0.1(2) . . . . ?
C5 N6 C1 N1 178.2(2) . . . . ?
C5 N6 C1 C2 0.0(3) . . . . ?
Se1 N2 C2 N3 179.30(16) . . . . ?
Se1 N2 C2 C1 0.3(2) . . . . ?
C4 N3 C2 N2 -178.3(2) . . . . ?
C4 N3 C2 C1 0.7(3) . . . . ?
N1 C1 C2 N2 -0.1(3) . . . . ?
N6 C1 C2 N2 178.2(2) . . . . ?
N1 C1 C2 N3 -179.12(19) . . . . ?
N6 C1 C2 N3 -0.8(3) . . . . ?
C2 N3 C4 C7 179.52(19) . . . . ?
C2 N3 C4 C5 0.2(3) . . . . ?
C1 N6 C5 C4 0.9(3) . . . . ?
C1 N6 C5 C8 -177.31(19) . . . . ?
N3 C4 C5 N6 -1.0(3) . . . . ?
C7 C4 C5 N6 179.6(2) . . . . ?
N3 C4 C5 C8 177.1(2) . . . . ?
C7 C4 C5 C8 -2.2(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1917744'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;NN Vorozhtsov Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'potassium 5,6-dicyano-1,2,5-selenadiazolo[3,4-b]pyrazinidile, complex with 18-crown-6'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 K N6 O6 Se'
_chemical_formula_sum            'C18 H24 K N6 O6 Se'
_chemical_formula_weight         538.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0108(5)
_cell_length_b                   19.0336(8)
_cell_length_c                   10.8353(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.018(2)
_cell_angle_gamma                90
_cell_volume                     2392.44(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.37

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.788
_shelx_estimated_absorpt_T_min   0.296
_shelx_estimated_absorpt_T_max   0.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5781
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46819
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         30.048
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6549
_reflns_number_gt                4215
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0540P)²+2.1368P] 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         6549
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_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
Se1 Se 0.51148(3) 0.37117(2) 0.87072(3) 0.04867(12) Uani 1 1 d . . . . .
K1 K 0.24556(5) 0.54569(3) 0.70188(6) 0.04432(16) Uani 1 1 d . . . . .
O3 O 0.0251(2) 0.56327(19) 0.7697(2) 0.0855(9) Uani 1 1 d . . . . .
O2 O 0.0833(2) 0.43434(14) 0.6828(3) 0.0761(8) Uani 1 1 d . . . . .
N4 N 0.5074(2) 0.57130(12) 0.8240(2) 0.0407(5) Uani 1 1 d . . . . .
N1 N 0.6400(2) 0.41058(13) 0.9728(3) 0.0525(7) Uani 1 1 d . . . . .
O6 O 0.3429(2) 0.5465(2) 0.4812(3) 0.0973(12) Uani 1 1 d . . . . .
O1 O 0.2176(2) 0.42919(17) 0.5075(3) 0.0858(10) Uani 1 1 d . . . . .
C3 C 0.5921(2) 0.61409(14) 0.8859(3) 0.0395(6) Uani 1 1 d . . . . .
C2 C 0.6312(2) 0.47864(14) 0.9482(3) 0.0373(6) Uani 1 1 d . . . . .
N2 N 0.4503(2) 0.45376(13) 0.8041(2) 0.0431(6) Uani 1 1 d . . . . .
C12C C 0.3473(4) 0.6115(5) 0.4160(5) 0.139(3) Uani 1 1 d . . . . .
H12A H 0.2779 0.6169 0.3470 0.167 Uiso 1 1 calc R U . . .
H12B H 0.4129 0.6113 0.3794 0.167 Uiso 1 1 calc R U . . .
C11C C 0.3575(5) 0.6710(5) 0.5068(7) 0.147(4) Uani 1 1 d . . . . .
H11A H 0.4224 0.6634 0.5803 0.176 Uiso 1 1 calc R U . . .
H11B H 0.3701 0.7144 0.4656 0.176 Uiso 1 1 calc R U . . .
O5 O 0.2570(3) 0.67507(17) 0.5449(3) 0.0957(11) Uani 1 1 d . . . . .
C10C C 0.2576(6) 0.7362(3) 0.6238(7) 0.138(3) Uani 1 1 d . . . . .
H10A H 0.3233 0.7342 0.6979 0.166 Uiso 1 1 calc R U . . .
H10B H 0.2643 0.7783 0.5759 0.166 Uiso 1 1 calc R U . . .
C9C C 0.1523(6) 0.7386(2) 0.6644(6) 0.128(3) Uani 1 1 d . . . . .
H9CA H 0.1483 0.7824 0.7088 0.154 Uiso 1 1 calc R U . . .
H9CB H 0.0864 0.7364 0.5904 0.154 Uiso 1 1 calc R U . . .
O4 O 0.1494(3) 0.68203(16) 0.7453(3) 0.0993(12) Uani 1 1 d . . . . .
C8C C 0.0498(6) 0.6837(4) 0.7944(6) 0.136(3) Uani 1 1 d . . . . .
H8CA H -0.0191 0.6897 0.7250 0.163 Uiso 1 1 calc R U . . .
H8CB H 0.0551 0.7228 0.8531 0.163 Uiso 1 1 calc R U . . .
C7C C 0.0443(5) 0.6173(4) 0.8609(5) 0.131(3) Uani 1 1 d . . . . .
H7CA H 0.1160 0.6092 0.9252 0.157 Uiso 1 1 calc R U . . .
H7CB H -0.0179 0.6187 0.9028 0.157 Uiso 1 1 calc R U . . .
C6C C -0.0043(4) 0.4965(4) 0.8154(5) 0.110(2) Uani 1 1 d . . . . .
H5 H 0.0574 0.4810 0.8871 0.133 Uiso 1 1 calc R U . . .
H4 H -0.0740 0.5010 0.8441 0.133 Uiso 1 1 calc R U . . .
C5C C -0.0217(4) 0.4457(3) 0.7129(6) 0.108(2) Uani 1 1 d . . . . .
H5CA H -0.0500 0.4020 0.7392 0.130 Uiso 1 1 calc R U . . .
H5CB H -0.0784 0.4632 0.6385 0.130 Uiso 1 1 calc R U . . .
C4C C 0.0763(5) 0.3794(2) 0.5910(6) 0.115(2) Uani 1 1 d . . . . .
H6 H 0.0201 0.3916 0.5121 0.138 Uiso 1 1 calc R U . . .
H7 H 0.0517 0.3361 0.6232 0.138 Uiso 1 1 calc R U . . .
C3C C 0.1908(6) 0.3692(3) 0.5661(6) 0.121(3) Uani 1 1 d . . . . .
H3CA H 0.2486 0.3611 0.6459 0.145 Uiso 1 1 calc R U . . .
H3CB H 0.1892 0.3288 0.5112 0.145 Uiso 1 1 calc R U . . .
C2C C 0.3248(4) 0.4239(4) 0.4744(5) 0.119(3) Uani 1 1 d . . . . .
H2CA H 0.3248 0.3826 0.4220 0.143 Uiso 1 1 calc R U . . .
H2CB H 0.3875 0.4196 0.5511 0.143 Uiso 1 1 calc R U . . .
C1C C 0.3408(4) 0.4875(5) 0.4035(4) 0.137(3) Uani 1 1 d . . . . .
H1CA H 0.4126 0.4842 0.3786 0.165 Uiso 1 1 calc R U . . .
H1CB H 0.2782 0.4917 0.3266 0.165 Uiso 1 1 calc R U . . .
C4 C 0.5779(3) 0.68821(18) 0.8592(3) 0.0607(9) Uani 1 1 d . . . . .
N5 N 0.5679(4) 0.74694(19) 0.8398(4) 0.1026(14) Uani 1 1 d . . . . .
C1 C 0.5268(2) 0.50246(14) 0.8553(2) 0.0333(5) Uani 1 1 d . . . . .
N3 N 0.7145(2) 0.52412(13) 1.0081(2) 0.0458(6) Uani 1 1 d . . . . .
N6 N 0.8480(3) 0.68342(18) 1.0724(4) 0.0859(11) Uani 1 1 d . . . . .
C5 C 0.6932(2) 0.59090(14) 0.9733(3) 0.0391(6) Uani 1 1 d . . . . .
C6 C 0.7802(3) 0.64246(17) 1.0309(3) 0.0546(8) 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 1.805(2) . ?
Se1 N1 1.812(3) . ?
K1 O2 2.850(2) . ?
K1 O6 2.921(3) . ?
K1 O4 2.928(3) . ?
K1 O3 2.945(3) . ?
K1 N2 2.987(3) . ?
K1 O1 3.016(3) . ?
K1 O5 3.016(3) . ?
K1 N4 3.118(2) . ?
K1 N3 3.330(3) 3_667 ?
K1 C1 3.455(3) . ?
O3 C7C 1.403(7) . ?
O3 C6C 1.441(6) . ?
O2 C5C 1.399(6) . ?
O2 C4C 1.431(6) . ?
N4 C3 1.340(4) . ?
N4 C1 1.358(3) . ?
N1 C2 1.321(4) . ?
O6 C1C 1.400(8) . ?
O6 C12C 1.432(8) . ?
O1 C3C 1.384(7) . ?
O1 C2C 1.427(6) . ?
C3 C5 1.404(4) . ?
C3 C4 1.441(4) . ?
C2 N3 1.355(4) . ?
C2 C1 1.462(4) . ?
N2 C1 1.322(3) . ?
C12C C11C 1.484(10) . ?
C12C H12A 0.9700 . ?
C12C H12B 0.9700 . ?
C11C O5 1.375(7) . ?
C11C H11A 0.9700 . ?
C11C H11B 0.9700 . ?
O5 C10C 1.442(7) . ?
C10C C9C 1.444(10) . ?
C10C H10A 0.9700 . ?
C10C H10B 0.9700 . ?
C9C O4 1.395(7) . ?
C9C H9CA 0.9700 . ?
C9C H9CB 0.9700 . ?
O4 C8C 1.429(7) . ?
C8C C7C 1.466(9) . ?
C8C H8CA 0.9700 . ?
C8C H8CB 0.9700 . ?
C7C H7CA 0.9700 . ?
C7C H7CB 0.9700 . ?
C6C C5C 1.445(8) . ?
C6C H5 0.9700 . ?
C6C H4 0.9700 . ?
C5C H5CA 0.9700 . ?
C5C H5CB 0.9700 . ?
C4C C3C 1.480(9) . ?
C4C H6 0.9700 . ?
C4C H7 0.9700 . ?
C3C H3CA 0.9700 . ?
C3C H3CB 0.9700 . ?
C2C C1C 1.471(9) . ?
C2C H2CA 0.9700 . ?
C2C H2CB 0.9700 . ?
C1C H1CA 0.9700 . ?
C1C H1CB 0.9700 . ?
C4 N5 1.138(4) . ?
N3 C5 1.332(4) . ?
N3 K1 3.330(3) 3_667 ?
N6 C6 1.132(4) . ?
C5 C6 1.451(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 94.46(11) . . ?
O2 K1 O6 110.83(11) . . ?
O2 K1 O4 112.32(11) . . ?
O6 K1 O4 112.66(12) . . ?
O2 K1 O3 57.34(10) . . ?
O6 K1 O3 141.26(8) . . ?
O4 K1 O3 56.04(11) . . ?
O2 K1 N2 94.19(7) . . ?
O6 K1 N2 80.85(8) . . ?
O4 K1 N2 141.33(8) . . ?
O3 K1 N2 132.93(8) . . ?
O2 K1 O1 56.79(10) . . ?
O6 K1 O1 55.12(11) . . ?
O4 K1 O1 141.87(8) . . ?
O3 K1 O1 108.24(9) . . ?
N2 K1 O1 76.14(7) . . ?
O2 K1 O5 134.14(8) . . ?
O6 K1 O5 56.47(11) . . ?
O4 K1 O5 56.27(11) . . ?
O3 K1 O5 102.91(10) . . ?
N2 K1 O5 122.26(8) . . ?
O1 K1 O5 102.68(11) . . ?
O2 K1 N4 137.95(7) . . ?
O6 K1 N4 76.90(8) . . ?
O4 K1 N4 100.94(8) . . ?
O3 K1 N4 138.55(8) . . ?
N2 K1 N4 44.88(6) . . ?
O1 K1 N4 109.21(7) . . ?
O5 K1 N4 85.60(7) . . ?
O2 K1 N3 72.56(7) . 3_667 ?
O6 K1 N3 141.65(8) . 3_667 ?
O4 K1 N3 99.69(8) . 3_667 ?
O3 K1 N3 74.27(7) . 3_667 ?
N2 K1 N3 60.86(6) . 3_667 ?
O1 K1 N3 109.17(8) . 3_667 ?
O5 K1 N3 147.29(9) . 3_667 ?
N4 K1 N3 77.23(6) . 3_667 ?
O2 K1 C1 115.00(7) . . ?
O6 K1 C1 81.17(7) . . ?
O4 K1 C1 120.73(8) . . ?
O3 K1 C1 137.49(7) . . ?
N2 K1 C1 22.18(6) . . ?
O1 K1 C1 94.54(7) . . ?
O5 K1 C1 106.49(7) . . ?
N4 K1 C1 23.12(6) . . ?
N3 K1 C1 64.35(6) 3_667 . ?
C7C O3 C6C 114.5(4) . . ?
C7C O3 K1 105.3(3) . . ?
C6C O3 K1 107.5(2) . . ?
C5C O2 C4C 112.5(4) . . ?
C5C O2 K1 120.6(3) . . ?
C4C O2 K1 120.6(3) . . ?
C3 N4 C1 113.7(2) . . ?
C3 N4 K1 149.24(19) . . ?
C1 N4 K1 92.53(15) . . ?
C2 N1 Se1 105.76(19) . . ?
C1C O6 C12C 113.2(5) . . ?
C1C O6 K1 122.6(4) . . ?
C12C O6 K1 118.8(4) . . ?
C3C O1 C2C 112.9(4) . . ?
C3C O1 K1 106.4(3) . . ?
C2C O1 K1 106.4(3) . . ?
N4 C3 C5 124.0(2) . . ?
N4 C3 C4 117.4(2) . . ?
C5 C3 C4 118.7(3) . . ?
N1 C2 N3 121.3(2) . . ?
N1 C2 C1 116.9(2) . . ?
N3 C2 C1 121.8(2) . . ?
C1 N2 Se1 106.02(18) . . ?
C1 N2 K1 99.25(17) . . ?
Se1 N2 K1 150.37(12) . . ?
O6 C12C C11C 109.8(4) . . ?
O6 C12C H12A 109.7 . . ?
C11C C12C H12A 109.7 . . ?
O6 C12C H12B 109.7 . . ?
C11C C12C H12B 109.7 . . ?
H12A C12C H12B 108.2 . . ?
O5 C11C C12C 108.3(5) . . ?
O5 C11C H11A 110.0 . . ?
C12C C11C H11A 110.0 . . ?
O5 C11C H11B 110.0 . . ?
C12C C11C H11B 110.0 . . ?
H11A C11C H11B 108.4 . . ?
C11C O5 C10C 110.8(5) . . ?
C11C O5 K1 107.1(3) . . ?
C10C O5 K1 108.5(3) . . ?
C9C C10C O5 109.7(4) . . ?
C9C C10C H10A 109.7 . . ?
O5 C10C H10A 109.7 . . ?
C9C C10C H10B 109.7 . . ?
O5 C10C H10B 109.7 . . ?
H10A C10C H10B 108.2 . . ?
O4 C9C C10C 109.5(4) . . ?
O4 C9C H9CA 109.8 . . ?
C10C C9C H9CA 109.8 . . ?
O4 C9C H9CB 109.8 . . ?
C10C C9C H9CB 109.8 . . ?
H9CA C9C H9CB 108.2 . . ?
C9C O4 C8C 112.1(4) . . ?
C9C O4 K1 120.5(4) . . ?
C8C O4 K1 118.9(3) . . ?
O4 C8C C7C 108.2(4) . . ?
O4 C8C H8CA 110.1 . . ?
C7C C8C H8CA 110.1 . . ?
O4 C8C H8CB 110.1 . . ?
C7C C8C H8CB 110.1 . . ?
H8CA C8C H8CB 108.4 . . ?
O3 C7C C8C 107.8(4) . . ?
O3 C7C H7CA 110.1 . . ?
C8C C7C H7CA 110.1 . . ?
O3 C7C H7CB 110.1 . . ?
C8C C7C H7CB 110.1 . . ?
H7CA C7C H7CB 108.5 . . ?
C5C C6C O3 108.9(4) . . ?
C5C C6C H5 109.9 . . ?
O3 C6C H5 109.9 . . ?
C5C C6C H4 109.9 . . ?
O3 C6C H4 109.9 . . ?
H5 C6C H4 108.3 . . ?
O2 C5C C6C 108.9(4) . . ?
O2 C5C H5CA 109.9 . . ?
C6C C5C H5CA 109.9 . . ?
O2 C5C H5CB 109.9 . . ?
C6C C5C H5CB 109.9 . . ?
H5CA C5C H5CB 108.3 . . ?
O2 C4C C3C 109.4(4) . . ?
O2 C4C H6 109.8 . . ?
C3C C4C H6 109.8 . . ?
O2 C4C H7 109.8 . . ?
C3C C4C H7 109.8 . . ?
H6 C4C H7 108.2 . . ?
O1 C3C C4C 108.2(4) . . ?
O1 C3C H3CA 110.0 . . ?
C4C C3C H3CA 110.0 . . ?
O1 C3C H3CB 110.0 . . ?
C4C C3C H3CB 110.0 . . ?
H3CA C3C H3CB 108.4 . . ?
O1 C2C C1C 108.8(4) . . ?
O1 C2C H2CA 109.9 . . ?
C1C C2C H2CA 109.9 . . ?
O1 C2C H2CB 109.9 . . ?
C1C C2C H2CB 109.9 . . ?
H2CA C2C H2CB 108.3 . . ?
O6 C1C C2C 109.3(4) . . ?
O6 C1C H1CA 109.8 . . ?
C2C C1C H1CA 109.8 . . ?
O6 C1C H1CB 109.8 . . ?
C2C C1C H1CB 109.8 . . ?
H1CA C1C H1CB 108.3 . . ?
N5 C4 C3 179.0(4) . . ?
N2 C1 N4 121.1(2) . . ?
N2 C1 C2 116.8(2) . . ?
N4 C1 C2 122.1(2) . . ?
N2 C1 K1 58.56(14) . . ?
N4 C1 K1 64.34(14) . . ?
C2 C1 K1 164.22(18) . . ?
C5 N3 C2 114.2(2) . . ?
C5 N3 K1 128.17(19) . 3_667 ?
C2 N3 K1 96.01(17) . 3_667 ?
N3 C5 C3 124.1(2) . . ?
N3 C5 C6 117.4(2) . . ?
C3 C5 C6 118.6(3) . . ?
N6 C6 C5 178.0(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
N2 Se1 N1 C2 -2.1(2) . . . . ?
C1 N4 C3 C5 1.2(4) . . . . ?
K1 N4 C3 C5 147.7(3) . . . . ?
C1 N4 C3 C4 -179.4(3) . . . . ?
K1 N4 C3 C4 -33.0(5) . . . . ?
Se1 N1 C2 N3 -179.4(2) . . . . ?
Se1 N1 C2 C1 1.6(3) . . . . ?
N1 Se1 N2 C1 2.2(2) . . . . ?
N1 Se1 N2 K1 -145.4(2) . . . . ?
C1C O6 C12C C11C -176.1(4) . . . . ?
K1 O6 C12C C11C 29.1(5) . . . . ?
O6 C12C C11C O5 -66.7(6) . . . . ?
C12C C11C O5 C10C -174.5(4) . . . . ?
C12C C11C O5 K1 67.3(5) . . . . ?
C11C O5 C10C C9C -179.0(5) . . . . ?
K1 O5 C10C C9C -61.6(5) . . . . ?
O5 C10C C9C O4 66.2(6) . . . . ?
C10C C9C O4 C8C 176.8(5) . . . . ?
C10C C9C O4 K1 -35.6(5) . . . . ?
C9C O4 C8C C7C 171.0(4) . . . . ?
K1 O4 C8C C7C 22.9(5) . . . . ?
C6C O3 C7C C8C -168.8(4) . . . . ?
K1 O3 C7C C8C 73.3(5) . . . . ?
O4 C8C C7C O3 -65.6(6) . . . . ?
C7C O3 C6C C5C -180.0(4) . . . . ?
K1 O3 C6C C5C -63.3(4) . . . . ?
C4C O2 C5C C6C 174.0(4) . . . . ?
K1 O2 C5C C6C -33.8(5) . . . . ?
O3 C6C C5C O2 66.0(5) . . . . ?
C5C O2 C4C C3C -178.7(4) . . . . ?
K1 O2 C4C C3C 29.1(6) . . . . ?
C2C O1 C3C C4C -177.6(4) . . . . ?
K1 O1 C3C C4C 66.0(4) . . . . ?
O2 C4C C3C O1 -65.9(6) . . . . ?
C3C O1 C2C C1C 175.3(4) . . . . ?
K1 O1 C2C C1C -68.3(4) . . . . ?
C12C O6 C1C C2C -174.5(4) . . . . ?
K1 O6 C1C C2C -20.7(5) . . . . ?
O1 C2C C1C O6 60.7(5) . . . . ?
Se1 N2 C1 N4 179.5(2) . . . . ?
K1 N2 C1 N4 -16.2(3) . . . . ?
Se1 N2 C1 C2 -1.7(3) . . . . ?
K1 N2 C1 C2 162.72(19) . . . . ?
Se1 N2 C1 K1 -164.39(18) . . . . ?
C3 N4 C1 N2 178.8(3) . . . . ?
K1 N4 C1 N2 15.3(3) . . . . ?
C3 N4 C1 C2 0.0(4) . . . . ?
K1 N4 C1 C2 -163.5(2) . . . . ?
C3 N4 C1 K1 163.6(3) . . . . ?
N1 C2 C1 N2 0.1(4) . . . . ?
N3 C2 C1 N2 -179.0(3) . . . . ?
N1 C2 C1 N4 178.9(3) . . . . ?
N3 C2 C1 N4 -0.1(4) . . . . ?
N1 C2 C1 K1 68.8(7) . . . . ?
N3 C2 C1 K1 -110.2(6) . . . . ?
N1 C2 N3 C5 -180.0(3) . . . . ?
C1 C2 N3 C5 -1.0(4) . . . . ?
N1 C2 N3 K1 -43.2(3) . . . 3_667 ?
C1 C2 N3 K1 135.8(2) . . . 3_667 ?
C2 N3 C5 C3 2.2(4) . . . . ?
K1 N3 C5 C3 -117.8(3) 3_667 . . . ?
C2 N3 C5 C6 -178.4(3) . . . . ?
K1 N3 C5 C6 61.6(3) 3_667 . . . ?
N4 C3 C5 N3 -2.5(5) . . . . ?
C4 C3 C5 N3 178.1(3) . . . . ?
N4 C3 C5 C6 178.1(3) . . . . ?
C4 C3 C5 C6 -1.3(5) . . . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1917746'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;NN Vorozhtsov Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'sodium 5,6-dicyano-1,2,5-selenadiazolo[3,4-b]pyrazinidile, complex with 18-crown-6 and thf'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 N6 Na O6 Se, C4 H8 O'
_chemical_formula_sum            'C22 H32 N6 Na O7 Se'
_chemical_formula_weight         594.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7796(7)
_cell_length_b                   14.7106(10)
_cell_length_c                   22.4551(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.426(3)
_cell_angle_gamma                90
_cell_volume                     2900.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.22

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             1228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.358
_shelx_estimated_absorpt_T_min   0.550
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8023
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57566
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.282
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6694
_reflns_number_gt                4650
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0359P)²+1.5311P] 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         6694
_refine_ls_number_parameters     344
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.052
_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
Se1 Se 0.26040(3) 0.71143(2) 0.22144(2) 0.04157(9) Uani 1 1 d . . . . .
Na1 Na 0.25645(10) 0.96082(5) 0.25399(4) 0.0409(2) Uani 1 1 d . . . . .
C6 C -0.1423(3) 0.80081(18) 0.43404(11) 0.0505(6) Uani 1 1 d . . . . .
O5 O 0.36959(18) 0.97245(12) 0.36905(7) 0.0468(4) Uani 1 1 d . . . . .
O6 O 0.08935(18) 1.05692(12) 0.34861(8) 0.0487(4) Uani 1 1 d . . . . .
O1 O -0.04303(19) 1.01261(11) 0.24012(8) 0.0485(4) Uani 1 1 d . . . . .
O2 O 0.13864(19) 0.95686(13) 0.14503(7) 0.0515(4) Uani 1 1 d . . . . .
O3 O 0.41302(18) 0.86885(11) 0.16620(7) 0.0432(4) Uani 1 1 d . . . . .
O4 O 0.55218(18) 0.91666(10) 0.27297(7) 0.0410(4) Uani 1 1 d . . . . .
N1 N 0.1682(2) 0.62052(11) 0.26163(8) 0.0387(4) Uani 1 1 d . . . . .
C1 C 0.0887(2) 0.65928(13) 0.30451(9) 0.0319(5) Uani 1 1 d . . . . .
N3 N 0.0056(2) 0.60940(12) 0.34329(8) 0.0387(4) Uani 1 1 d . . . . .
N4 N 0.0186(2) 0.80663(12) 0.34986(9) 0.0395(5) Uani 1 1 d . . . . .
C2 C 0.0950(2) 0.75892(14) 0.30783(10) 0.0327(5) Uani 1 1 d . . . . .
N2 N 0.1803(2) 0.80030(11) 0.26763(9) 0.0400(4) Uani 1 1 d . . . . .
C3 C -0.0663(3) 0.65920(15) 0.38455(10) 0.0373(5) Uani 1 1 d . . . . .
C4 C -0.0600(3) 0.75404(16) 0.38764(10) 0.0368(5) Uani 1 1 d . . . . .
N6 N -0.2095(3) 0.8375(2) 0.46994(11) 0.0752(8) Uani 1 1 d . . . . .
C16 C 0.3082(3) 1.0373(2) 0.40900(12) 0.0562(7) Uani 1 1 d . . . . .
H24 H 0.3406 1.0993 0.3975 0.067 Uiso 1 1 calc R U . . .
H25 H 0.3452 1.0252 0.4500 0.067 Uiso 1 1 calc R U . . .
C17 C 0.1390(3) 1.0302(2) 0.40642(12) 0.0564(7) Uani 1 1 d . . . . .
H22 H 0.1072 0.9669 0.4145 0.068 Uiso 1 1 calc R U . . .
H23 H 0.0931 1.0702 0.4369 0.068 Uiso 1 1 calc R U . . .
C18 C -0.0699(3) 1.04486(19) 0.34203(12) 0.0523(7) Uani 1 1 d . . . . .
H21 H -0.1242 1.0829 0.3714 0.063 Uiso 1 1 calc R U . . .
H20 H -0.0969 0.9805 0.3493 0.063 Uiso 1 1 calc R U . . .
C7 C -0.1158(3) 1.07124(17) 0.28081(12) 0.0508(6) Uani 1 1 d . . . . .
H18 H -0.2277 1.0664 0.2762 0.061 Uiso 1 1 calc R U . . .
H19 H -0.0858 1.1350 0.2730 0.061 Uiso 1 1 calc R U . . .
C8 C -0.0731(3) 1.0388(2) 0.18030(13) 0.0649(8) Uani 1 1 d . . . . .
H17 H -0.0182 1.0958 0.1710 0.078 Uiso 1 1 calc R U . . .
H16 H -0.1836 1.0497 0.1746 0.078 Uiso 1 1 calc R U . . .
C9 C -0.0221(3) 0.9654(3) 0.14027(13) 0.0690(9) Uani 1 1 d . . . . .
H15 H -0.0713 0.9074 0.1515 0.083 Uiso 1 1 calc R U . . .
H14 H -0.0512 0.9799 0.0987 0.083 Uiso 1 1 calc R U . . .
C10 C 0.1938(3) 0.8891(2) 0.10558(11) 0.0551(7) Uani 1 1 d . . . . .
H12 H 0.1568 0.9014 0.0646 0.066 Uiso 1 1 calc R U . . .
H13 H 0.1560 0.8286 0.1179 0.066 Uiso 1 1 calc R U . . .
C11 C 0.3633(3) 0.8904(2) 0.10722(11) 0.0531(7) Uani 1 1 d . . . . .
H10 H 0.4040 0.8453 0.0787 0.064 Uiso 1 1 calc R U . . .
H11 H 0.4010 0.9512 0.0957 0.064 Uiso 1 1 calc R U . . .
C12 C 0.5736(3) 0.87577(17) 0.17146(11) 0.0465(6) Uani 1 1 d . . . . .
H8 H 0.6066 0.9383 0.1617 0.056 Uiso 1 1 calc R U . . .
H9 H 0.6229 0.8333 0.1434 0.056 Uiso 1 1 calc R U . . .
C13 C 0.6189(3) 0.85299(16) 0.23364(11) 0.0454(6) Uani 1 1 d . . . . .
H6 H 0.5842 0.7908 0.2436 0.054 Uiso 1 1 calc R U . . .
H7 H 0.7313 0.8549 0.2377 0.054 Uiso 1 1 calc R U . . .
C14 C 0.5857(3) 0.89516(19) 0.33296(12) 0.0525(7) Uani 1 1 d . . . . .
H4 H 0.6969 0.8872 0.3383 0.063 Uiso 1 1 calc R U . . .
H5 H 0.5350 0.8375 0.3440 0.063 Uiso 1 1 calc R U . . .
C15 C 0.5307(3) 0.9704(2) 0.37201(12) 0.0566(7) Uani 1 1 d . . . . .
H2 H 0.5648 0.9600 0.4136 0.068 Uiso 1 1 calc R U . . .
H3 H 0.5728 1.0292 0.3584 0.068 Uiso 1 1 calc R U . . .
C5 C -0.1537(3) 0.60929(18) 0.42759(11) 0.0502(6) Uani 1 1 d . . . . .
N5 N -0.2236(3) 0.56924(19) 0.46118(10) 0.0758(8) Uani 1 1 d . . . . .
O1T O 0.2138(14) 0.2334(10) -0.0503(3) 0.154(6) Uani 0.54(2) 1 d . . P A 1
O1T' O 0.298(2) 0.2655(13) -0.0159(10) 0.227(10) Uani 0.46(2) 1 d . . P A 2
C4T C 0.1431(18) 0.2940(7) -0.0152(8) 0.313(8) Uani 1 1 d . . . . .
H1T H 0.0437 0.3113 -0.0329 0.376 Uiso 1 1 calc R U . A 1
H2T H 0.2060 0.3495 -0.0109 0.376 Uiso 1 1 calc R U . A 1
C3T C 0.1208(10) 0.2522(9) 0.0421(4) 0.228(5) Uani 1 1 d . U . . .
H3T H 0.0120 0.2535 0.0534 0.273 Uiso 1 1 calc R U . . .
H4T H 0.1813 0.2836 0.0733 0.273 Uiso 1 1 calc R U . . .
C2T C 0.1718(7) 0.1616(5) 0.0345(3) 0.155(2) Uani 1 1 d . . . . .
H5T H 0.2237 0.1386 0.0708 0.185 Uiso 1 1 calc R U . . .
H6T H 0.0865 0.1205 0.0239 0.185 Uiso 1 1 calc R U . . .
C1T C 0.2734(8) 0.1711(4) -0.0127(3) 0.1326(19) Uani 1 1 d . . . . .
H7T H 0.3741 0.1915 0.0022 0.159 Uiso 1 1 calc R U . A 1
H8T H 0.2866 0.1122 -0.0334 0.159 Uiso 1 1 calc R U . A 1


_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 1.8079(17) . ?
Se1 N2 1.8140(18) . ?
Na1 N1 2.4663(19) 2 ?
Na1 N2 2.4740(19) . ?
Na1 O2 2.6498(19) . ?
Na1 O4 2.7071(18) . ?
Na1 O1 2.7529(19) . ?
Na1 O3 2.7652(18) . ?
Na1 O5 2.7665(19) . ?
Na1 O6 2.9515(19) . ?
C6 N6 1.139(3) . ?
C6 C4 1.446(3) . ?
O5 C15 1.416(3) . ?
O5 C16 1.419(3) . ?
O6 C18 1.416(3) . ?
O6 C17 1.422(3) . ?
O1 C7 1.413(3) . ?
O1 C8 1.420(3) . ?
O2 C10 1.421(3) . ?
O2 C9 1.420(3) . ?
O3 C12 1.417(3) . ?
O3 C11 1.427(3) . ?
O4 C14 1.413(3) . ?
O4 C13 1.417(3) . ?
N1 C1 1.323(3) . ?
N1 Na1 2.4663(19) 2_545 ?
C1 N3 1.356(3) . ?
C1 C2 1.469(3) . ?
N3 C3 1.342(3) . ?
N4 C4 1.343(3) . ?
N4 C2 1.357(3) . ?
C2 N2 1.325(3) . ?
C3 C4 1.398(3) . ?
C3 C5 1.440(3) . ?
C16 C17 1.490(4) . ?
C16 H24 0.9900 . ?
C16 H25 0.9900 . ?
C17 H22 0.9900 . ?
C17 H23 0.9900 . ?
C18 C7 1.481(4) . ?
C18 H21 0.9900 . ?
C18 H20 0.9900 . ?
C7 H18 0.9900 . ?
C7 H19 0.9900 . ?
C8 C9 1.476(4) . ?
C8 H17 0.9900 . ?
C8 H16 0.9900 . ?
C9 H15 0.9900 . ?
C9 H14 0.9900 . ?
C10 C11 1.489(4) . ?
C10 H12 0.9900 . ?
C10 H13 0.9900 . ?
C11 H10 0.9900 . ?
C11 H11 0.9900 . ?
C12 C13 1.487(4) . ?
C12 H8 0.9900 . ?
C12 H9 0.9900 . ?
C13 H6 0.9900 . ?
C13 H7 0.9900 . ?
C14 C15 1.494(4) . ?
C14 H4 0.9900 . ?
C14 H5 0.9900 . ?
C15 H2 0.9900 . ?
C15 H3 0.9900 . ?
C5 N5 1.140(3) . ?
O1T C4T 1.345(14) . ?
O1T C1T 1.350(9) . ?
O1T' C1T 1.408(16) . ?
O1T' C4T 1.42(2) . ?
C4T C3T 1.442(13) . ?
C4T H1T 0.9900 . ?
C4T H2T 0.9900 . ?
C3T C2T 1.416(11) . ?
C3T H3T 0.9900 . ?
C3T H4T 0.9900 . ?
C2T C1T 1.398(7) . ?
C2T H5T 0.9900 . ?
C2T H6T 0.9900 . ?
C1T H7T 0.9900 . ?
C1T H8T 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se1 N2 94.06(8) . . ?
N1 Na1 N2 178.94(8) 2 . ?
N1 Na1 O2 89.60(7) 2 . ?
N2 Na1 O2 89.39(7) . . ?
N1 Na1 O4 89.61(6) 2 . ?
N2 Na1 O4 90.65(6) . . ?
O2 Na1 O4 120.49(6) . . ?
N1 Na1 O1 88.69(6) 2 . ?
N2 Na1 O1 91.10(6) . . ?
O2 Na1 O1 62.34(6) . . ?
O4 Na1 O1 176.69(6) . . ?
N1 Na1 O3 103.27(6) 2 . ?
N2 Na1 O3 75.97(6) . . ?
O2 Na1 O3 61.56(5) . . ?
O4 Na1 O3 60.89(5) . . ?
O1 Na1 O3 122.29(6) . . ?
N1 Na1 O5 88.80(7) 2 . ?
N2 Na1 O5 92.23(7) . . ?
O2 Na1 O5 177.03(6) . . ?
O4 Na1 O5 62.00(5) . . ?
O1 Na1 O5 115.12(6) . . ?
O3 Na1 O5 121.27(6) . . ?
N1 Na1 O6 77.37(6) 2 . ?
N2 Na1 O6 103.40(6) . . ?
O2 Na1 O6 118.85(6) . . ?
O4 Na1 O6 118.87(6) . . ?
O1 Na1 O6 57.96(5) . . ?
O3 Na1 O6 179.28(6) . . ?
O5 Na1 O6 58.33(5) . . ?
N6 C6 C4 178.7(3) . . ?
C15 O5 C16 111.63(19) . . ?
C15 O5 Na1 113.21(14) . . ?
C16 O5 Na1 119.78(15) . . ?
C18 O6 C17 110.90(19) . . ?
C18 O6 Na1 111.14(14) . . ?
C17 O6 Na1 111.97(14) . . ?
C7 O1 C8 111.3(2) . . ?
C7 O1 Na1 122.14(14) . . ?
C8 O1 Na1 110.67(14) . . ?
C10 O2 C9 111.0(2) . . ?
C10 O2 Na1 117.30(15) . . ?
C9 O2 Na1 116.64(15) . . ?
C12 O3 C11 111.02(18) . . ?
C12 O3 Na1 113.88(13) . . ?
C11 O3 Na1 113.76(14) . . ?
C14 O4 C13 111.22(18) . . ?
C14 O4 Na1 113.37(13) . . ?
C13 O4 Na1 117.46(13) . . ?
C1 N1 Se1 106.56(13) . . ?
C1 N1 Na1 131.12(14) . 2_545 ?
Se1 N1 Na1 120.81(9) . 2_545 ?
N1 C1 N3 121.59(18) . . ?
N1 C1 C2 116.59(19) . . ?
N3 C1 C2 121.83(19) . . ?
C3 N3 C1 113.95(18) . . ?
C4 N4 C2 113.59(18) . . ?
N2 C2 N4 121.38(18) . . ?
N2 C2 C1 116.41(19) . . ?
N4 C2 C1 122.2(2) . . ?
C2 N2 Se1 106.38(13) . . ?
C2 N2 Na1 132.64(14) . . ?
Se1 N2 Na1 120.71(9) . . ?
N3 C3 C4 124.1(2) . . ?
N3 C3 C5 116.1(2) . . ?
C4 C3 C5 119.8(2) . . ?
N4 C4 C3 124.3(2) . . ?
N4 C4 C6 116.3(2) . . ?
C3 C4 C6 119.4(2) . . ?
O5 C16 C17 108.1(2) . . ?
O5 C16 H24 110.1 . . ?
C17 C16 H24 110.1 . . ?
O5 C16 H25 110.1 . . ?
C17 C16 H25 110.1 . . ?
H24 C16 H25 108.4 . . ?
O6 C17 C16 108.4(2) . . ?
O6 C17 H22 110.0 . . ?
C16 C17 H22 110.0 . . ?
O6 C17 H23 110.0 . . ?
C16 C17 H23 110.0 . . ?
H22 C17 H23 108.4 . . ?
O6 C18 C7 109.0(2) . . ?
O6 C18 H21 109.9 . . ?
C7 C18 H21 109.9 . . ?
O6 C18 H20 109.9 . . ?
C7 C18 H20 109.9 . . ?
H21 C18 H20 108.3 . . ?
O1 C7 C18 108.6(2) . . ?
O1 C7 H18 110.0 . . ?
C18 C7 H18 110.0 . . ?
O1 C7 H19 110.0 . . ?
C18 C7 H19 110.0 . . ?
H18 C7 H19 108.4 . . ?
O1 C8 C9 108.8(2) . . ?
O1 C8 H17 109.9 . . ?
C9 C8 H17 109.9 . . ?
O1 C8 H16 109.9 . . ?
C9 C8 H16 109.9 . . ?
H17 C8 H16 108.3 . . ?
O2 C9 C8 109.0(2) . . ?
O2 C9 H15 109.9 . . ?
C8 C9 H15 109.9 . . ?
O2 C9 H14 109.9 . . ?
C8 C9 H14 109.9 . . ?
H15 C9 H14 108.3 . . ?
O2 C10 C11 108.7(2) . . ?
O2 C10 H12 109.9 . . ?
C11 C10 H12 109.9 . . ?
O2 C10 H13 109.9 . . ?
C11 C10 H13 109.9 . . ?
H12 C10 H13 108.3 . . ?
O3 C11 C10 108.6(2) . . ?
O3 C11 H10 110.0 . . ?
C10 C11 H10 110.0 . . ?
O3 C11 H11 110.0 . . ?
C10 C11 H11 110.0 . . ?
H10 C11 H11 108.3 . . ?
O3 C12 C13 108.75(19) . . ?
O3 C12 H8 109.9 . . ?
C13 C12 H8 109.9 . . ?
O3 C12 H9 109.9 . . ?
C13 C12 H9 109.9 . . ?
H8 C12 H9 108.3 . . ?
O4 C13 C12 109.08(19) . . ?
O4 C13 H6 109.9 . . ?
C12 C13 H6 109.9 . . ?
O4 C13 H7 109.9 . . ?
C12 C13 H7 109.9 . . ?
H6 C13 H7 108.3 . . ?
O4 C14 C15 109.1(2) . . ?
O4 C14 H4 109.9 . . ?
C15 C14 H4 109.9 . . ?
O4 C14 H5 109.9 . . ?
C15 C14 H5 109.9 . . ?
H4 C14 H5 108.3 . . ?
O5 C15 C14 108.4(2) . . ?
O5 C15 H2 110.0 . . ?
C14 C15 H2 110.0 . . ?
O5 C15 H3 110.0 . . ?
C14 C15 H3 110.0 . . ?
H2 C15 H3 108.4 . . ?
N5 C5 C3 179.3(3) . . ?
C4T O1T C1T 105.2(8) . . ?
C1T O1T' C4T 98.2(9) . . ?
O1T C4T C3T 107.9(7) . . ?
C3T C4T O1T' 91.1(13) . . ?
O1T C4T H1T 110.1 . . ?
C3T C4T H1T 110.1 . . ?
O1T C4T H2T 110.1 . . ?
C3T C4T H2T 110.1 . . ?
H1T C4T H2T 108.4 . . ?
C4T C3T C2T 104.4(6) . . ?
C4T C3T H3T 110.9 . . ?
C2T C3T H3T 110.9 . . ?
C4T C3T H4T 110.9 . . ?
C2T C3T H4T 110.9 . . ?
H3T C3T H4T 108.9 . . ?
C1T C2T C3T 101.7(6) . . ?
C1T C2T H5T 111.4 . . ?
C3T C2T H5T 111.4 . . ?
C1T C2T H6T 111.4 . . ?
C3T C2T H6T 111.4 . . ?
H5T C2T H6T 109.3 . . ?
O1T' C1T C2T 103.6(8) . . ?
O1T C1T C2T 107.2(6) . . ?
O1T C1T H7T 110.3 . . ?
C2T C1T H7T 110.3 . . ?
O1T C1T H8T 110.3 . . ?
C2T C1T H8T 110.3 . . ?
H7T C1T H8T 108.5 . . ?

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
N2 Se1 N1 C1 -0.22(17) . . . . ?
N2 Se1 N1 Na1 -167.70(12) . . . 2_545 ?
Se1 N1 C1 N3 -179.83(17) . . . . ?
Na1 N1 C1 N3 -14.1(3) 2_545 . . . ?
Se1 N1 C1 C2 0.3(2) . . . . ?
Na1 N1 C1 C2 165.99(15) 2_545 . . . ?
N1 C1 N3 C3 179.0(2) . . . . ?
C2 C1 N3 C3 -1.1(3) . . . . ?
C4 N4 C2 N2 -178.9(2) . . . . ?
C4 N4 C2 C1 0.7(3) . . . . ?
N1 C1 C2 N2 -0.3(3) . . . . ?
N3 C1 C2 N2 179.9(2) . . . . ?
N1 C1 C2 N4 -179.9(2) . . . . ?
N3 C1 C2 N4 0.2(3) . . . . ?
N4 C2 N2 Se1 179.70(17) . . . . ?
C1 C2 N2 Se1 0.1(2) . . . . ?
N4 C2 N2 Na1 5.8(3) . . . . ?
C1 C2 N2 Na1 -173.83(15) . . . . ?
N1 Se1 N2 C2 0.08(17) . . . . ?
N1 Se1 N2 Na1 174.87(12) . . . . ?
C1 N3 C3 C4 1.1(3) . . . . ?
C1 N3 C3 C5 -178.8(2) . . . . ?
C2 N4 C4 C3 -0.8(3) . . . . ?
C2 N4 C4 C6 179.2(2) . . . . ?
N3 C3 C4 N4 -0.1(4) . . . . ?
C5 C3 C4 N4 179.7(2) . . . . ?
N3 C3 C4 C6 179.9(2) . . . . ?
C5 C3 C4 C6 -0.3(4) . . . . ?
C15 O5 C16 C17 -175.8(2) . . . . ?
Na1 O5 C16 C17 48.5(3) . . . . ?
C18 O6 C17 C16 175.5(2) . . . . ?
Na1 O6 C17 C16 50.8(2) . . . . ?
O5 C16 C17 O6 -65.5(3) . . . . ?
C17 O6 C18 C7 -178.6(2) . . . . ?
Na1 O6 C18 C7 -53.3(2) . . . . ?
C8 O1 C7 C18 -175.5(2) . . . . ?
Na1 O1 C7 C18 -41.6(2) . . . . ?
O6 C18 C7 O1 62.7(3) . . . . ?
C7 O1 C8 C9 -168.4(2) . . . . ?
Na1 O1 C8 C9 52.3(3) . . . . ?
C10 O2 C9 C8 -177.9(2) . . . . ?
Na1 O2 C9 C8 44.2(3) . . . . ?
O1 C8 C9 O2 -65.0(3) . . . . ?
C9 O2 C10 C11 173.5(2) . . . . ?
Na1 O2 C10 C11 -48.9(2) . . . . ?
C12 O3 C11 C10 -175.6(2) . . . . ?
Na1 O3 C11 C10 -45.6(2) . . . . ?
O2 C10 C11 O3 61.9(3) . . . . ?
C11 O3 C12 C13 179.8(2) . . . . ?
Na1 O3 C12 C13 49.9(2) . . . . ?
C14 O4 C13 C12 177.0(2) . . . . ?
Na1 O4 C13 C12 44.1(2) . . . . ?
O3 C12 C13 O4 -61.9(2) . . . . ?
C13 O4 C14 C15 172.6(2) . . . . ?
Na1 O4 C14 C15 -52.4(2) . . . . ?
C16 O5 C15 C14 175.0(2) . . . . ?
Na1 O5 C15 C14 -46.3(3) . . . . ?
O4 C14 C15 O5 66.7(3) . . . . ?
C1T O1T C4T C3T -17.7(19) . . . . ?
C1T O1T' C4T C3T 60.3(15) . . . . ?
O1T C4T C3T C2T -5.1(18) . . . . ?
O1T' C4T C3T C2T -52.8(15) . . . . ?
C4T C3T C2T C1T 24.7(12) . . . . ?
C4T O1T' C1T C2T -49.3(16) . . . . ?
C4T O1T C1T C2T 34.9(15) . . . . ?
C3T C2T C1T O1T' 14.6(13) . . . . ?
C3T C2T C1T O1T -37.3(10) . . . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_2_thf
_database_code_depnum_ccdc_archive 'CCDC 1917745'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;NN Vorozhtsov Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'potassium 5,6-dicyano-1,2,5-selenadiazolo[3,4-b]pyrazinidile, complex with 18-crown-6 and thf'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 K N6 O6 Se, C4 H8 O'

_chemical_formula_sum            'C22 H32 K N6 O7 Se'
_chemical_formula_weight         610.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3642(7)
_cell_length_b                   9.2915(5)
_cell_length_c                   24.4420(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.661(3)
_cell_angle_gamma                90
_cell_volume                     2804.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5116
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      19.53

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             1260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.537
_shelx_estimated_absorpt_T_min   0.593
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8457
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32646
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6388
_reflns_number_gt                3442
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0593P)²+0.2952P] 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         6388
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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 0.44783(3) -0.30038(4) 1.00427(2) 0.05793(16) Uani 1 1 d . . . . .
N1 N 0.5524(2) -0.2168(3) 0.96591(12) 0.0498(7) Uani 1 1 d . . . . .
N2 N 0.4755(2) -0.1954(3) 1.06558(12) 0.0575(8) Uani 1 1 d . . . . .
N3 N 0.8812(3) 0.2138(5) 0.99713(17) 0.0991(14) Uani 1 1 d . . . . .
N4 N 0.7893(3) 0.2171(5) 1.14781(17) 0.0933(13) Uani 1 1 d . . . . .
N5 N 0.6024(2) -0.0203(3) 1.09317(12) 0.0526(7) Uani 1 1 d . . . . .
N6 N 0.6839(2) -0.0402(3) 0.98385(12) 0.0475(7) Uani 1 1 d . . . . .
C1 C 0.6007(3) -0.1232(3) 1.00024(14) 0.0426(8) Uani 1 1 d . . . . .
C2 C 0.5591(3) -0.1120(3) 1.05457(14) 0.0438(8) Uani 1 1 d . . . . .
C3 C 0.7244(3) 0.0480(4) 1.02326(15) 0.0482(9) Uani 1 1 d . . . . .
C4 C 0.6860(3) 0.0552(4) 1.07619(14) 0.0485(9) Uani 1 1 d . . . . .
C5 C 0.8127(3) 0.1405(5) 1.00858(16) 0.0630(10) Uani 1 1 d . . . . .
C6 C 0.7426(3) 0.1473(5) 1.11623(18) 0.0658(11) Uani 1 1 d . . . . .
K1 K 0.63559(6) -0.10121(8) 0.86160(3) 0.0551(2) Uani 1 1 d . . . . .
O1 O 0.87124(19) -0.0441(3) 0.84894(11) 0.0620(7) Uani 1 1 d . . . . .
O2 O 0.7133(2) 0.1566(3) 0.80951(11) 0.0644(7) Uani 1 1 d . . . . .
O3 O 0.5212(2) 0.0364(3) 0.76216(11) 0.0656(7) Uani 1 1 d . . . . .
O4 O 0.4600(2) -0.2357(3) 0.80000(11) 0.0635(7) Uani 1 1 d . . . . .
O5 O 0.6164(2) -0.4284(3) 0.84287(10) 0.0602(7) Uani 1 1 d . . . . .
O6 O 0.80982(19) -0.3111(2) 0.88786(11) 0.0599(7) Uani 1 1 d . . . . .
C1C C 0.9267(3) -0.1102(4) 0.89455(17) 0.0688(11) Uani 1 1 d . . . . .
H16 H 0.8940 -0.0818 0.9282 0.083 Uiso 1 1 calc R U . . .
H15 H 1.0019 -0.0800 0.8966 0.083 Uiso 1 1 calc R U . . .
C2C C 0.8873(3) 0.1072(4) 0.84849(18) 0.0708(12) Uani 1 1 d . . . . .
H17 H 0.9636 0.1285 0.8457 0.085 Uiso 1 1 calc R U . . .
H3 H 0.8636 0.1487 0.8823 0.085 Uiso 1 1 calc R U . . .
C3C C 0.8245(4) 0.1706(4) 0.80112(18) 0.0692(12) Uani 1 1 d . . . . .
H3CA H 0.8430 0.2715 0.7974 0.083 Uiso 1 1 calc R U . . .
H3CB H 0.8422 0.1214 0.7677 0.083 Uiso 1 1 calc R U . . .
C4C C 0.6492(4) 0.2256(4) 0.76748(18) 0.0757(13) Uani 1 1 d . . . . .
H5 H 0.6722 0.1955 0.7319 0.091 Uiso 1 1 calc R U . . .
H6 H 0.6576 0.3292 0.7703 0.091 Uiso 1 1 calc R U . . .
C5C C 0.5345(4) 0.1859(4) 0.77355(19) 0.0762(13) Uani 1 1 d . . . . .
H1 H 0.5138 0.2063 0.8106 0.091 Uiso 1 1 calc R U . . .
H7 H 0.4884 0.2419 0.7484 0.091 Uiso 1 1 calc R U . . .
C6C C 0.4111(3) -0.0082(5) 0.76328(17) 0.0699(11) Uani 1 1 d . . . . .
H8 H 0.3685 0.0402 0.7345 0.084 Uiso 1 1 calc R U . . .
H9 H 0.3821 0.0173 0.7982 0.084 Uiso 1 1 calc R U . . .
C7C C 0.4048(3) -0.1665(5) 0.75521(18) 0.0714(12) Uani 1 1 d . . . . .
H7CA H 0.3297 -0.1968 0.7528 0.086 Uiso 1 1 calc R U . . .
H7CB H 0.4377 -0.1927 0.7213 0.086 Uiso 1 1 calc R U . . .
C8C C 0.4449(3) -0.3872(4) 0.80001(18) 0.0690(12) Uani 1 1 d . . . . .
H8CA H 0.4711 -0.4282 0.7666 0.083 Uiso 1 1 calc R U . . .
H8CB H 0.3684 -0.4094 0.8015 0.083 Uiso 1 1 calc R U . . .
C9C C 0.5049(3) -0.4499(4) 0.84812(18) 0.0662(11) Uani 1 1 d . . . . .
H9CA H 0.4820 -0.4043 0.8814 0.079 Uiso 1 1 calc R U . . .
H9CB H 0.4896 -0.5521 0.8504 0.079 Uiso 1 1 calc R U . . .
C10C C 0.6789(3) -0.4958(4) 0.88674(17) 0.0667(11) Uani 1 1 d . . . . .
H14 H 0.6685 -0.5992 0.8855 0.080 Uiso 1 1 calc R U . . .
H2 H 0.6558 -0.4609 0.9217 0.080 Uiso 1 1 calc R U . . .
C11C C 0.7950(3) -0.4604(4) 0.88044(18) 0.0683(11) Uani 1 1 d . . . . .
H11A H 0.8396 -0.5128 0.9073 0.082 Uiso 1 1 calc R U . . .
H11B H 0.8163 -0.4882 0.8442 0.082 Uiso 1 1 calc R U . . .
C12C C 0.9199(3) -0.2684(4) 0.88769(18) 0.0668(11) Uani 1 1 d . . . . .
H12A H 0.9504 -0.2962 0.8534 0.080 Uiso 1 1 calc R U . . .
H12B H 0.9609 -0.3157 0.9173 0.080 Uiso 1 1 calc R U . . .
O1T O 0.8367(5) -0.2547(7) 1.1096(3) 0.207(3) Uani 1 1 d . . . . .
C1T C 0.8977(6) -0.3079(13) 1.0725(5) 0.269(8) Uani 1 1 d . . . . .
H1TA H 0.9569 -0.3611 1.0903 0.323 Uiso 1 1 calc R U . . .
H1TB H 0.9284 -0.2297 1.0520 0.323 Uiso 1 1 calc R U . . .
C2T C 0.8408(8) -0.3977(10) 1.0369(3) 0.176(3) Uani 1 1 d . . . . .
H2TA H 0.8821 -0.4835 1.0293 0.211 Uiso 1 1 calc R U . . .
H2TB H 0.8215 -0.3491 1.0027 0.211 Uiso 1 1 calc R U . . .
C3T C 0.7419(6) -0.4336(7) 1.0676(4) 0.156(3) Uani 1 1 d . . . . .
H24 H 0.6768 -0.3964 1.0490 0.187 Uiso 1 1 calc R U . . .
H22 H 0.7346 -0.5367 1.0725 0.187 Uiso 1 1 calc R U . . .
C4T C 0.7643(5) -0.3614(9) 1.1192(3) 0.143(3) Uani 1 1 d . . . . .
H4TA H 0.6983 -0.3211 1.1328 0.172 Uiso 1 1 calc R U . . .
H4TB H 0.7946 -0.4284 1.1462 0.172 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 1.807(3) . ?
Se1 N2 1.807(3) . ?
N1 C1 1.330(4) . ?
N1 K1 2.992(3) . ?
N2 C2 1.329(4) . ?
N3 C5 1.133(5) . ?
N4 C6 1.144(5) . ?
N5 C4 1.332(4) . ?
N5 C2 1.362(4) . ?
N5 K1 3.384(3) 3_657 ?
N6 C3 1.343(4) . ?
N6 C1 1.361(4) . ?
N6 K1 3.072(3) . ?
C1 C2 1.450(5) . ?
C1 K1 3.442(3) . ?
C3 C4 1.400(5) . ?
C3 C5 1.448(5) . ?
C4 C6 1.454(5) . ?
K1 O4 2.870(2) . ?
K1 O2 2.898(3) . ?
K1 O6 2.954(2) . ?
K1 O1 2.992(3) . ?
K1 O3 3.037(3) . ?
K1 O5 3.082(3) . ?
K1 N5 3.384(3) 3_657 ?
O1 C2C 1.420(4) . ?
O1 C1C 1.421(4) . ?
O2 C3C 1.406(5) . ?
O2 C4C 1.421(5) . ?
O3 C6C 1.424(4) . ?
O3 C5C 1.425(4) . ?
O4 C8C 1.420(4) . ?
O4 C7C 1.417(5) . ?
O5 C9C 1.405(4) . ?
O5 C10C 1.436(4) . ?
O6 C11C 1.410(4) . ?
O6 C12C 1.418(4) . ?
C1C C12C 1.481(5) . ?
C1C H16 0.9700 . ?
C1C H15 0.9700 . ?
C2C C3C 1.486(6) . ?
C2C H17 0.9700 . ?
C2C H3 0.9700 . ?
C3C H3CA 0.9700 . ?
C3C H3CB 0.9700 . ?
C4C C5C 1.480(6) . ?
C4C H5 0.9700 . ?
C4C H6 0.9700 . ?
C5C H1 0.9700 . ?
C5C H7 0.9700 . ?
C6C C7C 1.485(5) . ?
C6C H8 0.9700 . ?
C6C H9 0.9700 . ?
C7C H7CA 0.9700 . ?
C7C H7CB 0.9700 . ?
C8C C9C 1.480(5) . ?
C8C H8CA 0.9700 . ?
C8C H8CB 0.9700 . ?
C9C H9CA 0.9700 . ?
C9C H9CB 0.9700 . ?
C10C C11C 1.487(5) . ?
C10C H14 0.9700 . ?
C10C H2 0.9700 . ?
C11C H11A 0.9700 . ?
C11C H11B 0.9700 . ?
C12C H12A 0.9700 . ?
C12C H12B 0.9700 . ?
O1T C1T 1.304(8) . ?
O1T C4T 1.363(7) . ?
C1T C2T 1.375(10) . ?
C1T H1TA 0.9700 . ?
C1T H1TB 0.9700 . ?
C2T C3T 1.501(9) . ?
C2T H2TA 0.9700 . ?
C2T H2TB 0.9700 . ?
C3T C4T 1.445(9) . ?
C3T H24 0.9700 . ?
C3T H22 0.9700 . ?
C4T H4TA 0.9700 . ?
C4T H4TB 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
N1 Se1 N2 94.93(13) . . ?
C1 N1 Se1 105.3(2) . . ?
C1 N1 K1 98.1(2) . . ?
Se1 N1 K1 151.49(14) . . ?
C2 N2 Se1 105.4(2) . . ?
C4 N5 C2 113.6(3) . . ?
C4 N5 K1 128.7(2) . 3_657 ?
C2 N5 K1 96.64(19) . 3_657 ?
C3 N6 C1 113.3(3) . . ?
C3 N6 K1 149.2(2) . . ?
C1 N6 K1 93.80(19) . . ?
N1 C1 N6 120.5(3) . . ?
N1 C1 C2 117.2(3) . . ?
N6 C1 C2 122.3(3) . . ?
N1 C1 K1 59.40(18) . . ?
N6 C1 K1 62.96(17) . . ?
C2 C1 K1 164.5(2) . . ?
N2 C2 N5 120.6(3) . . ?
N2 C2 C1 117.1(3) . . ?
N5 C2 C1 122.3(3) . . ?
N6 C3 C4 124.1(3) . . ?
N6 C3 C5 116.4(3) . . ?
C4 C3 C5 119.5(3) . . ?
N5 C4 C3 124.3(3) . . ?
N5 C4 C6 117.2(3) . . ?
C3 C4 C6 118.5(3) . . ?
N3 C5 C3 179.4(5) . . ?
N4 C6 C4 178.2(5) . . ?
O4 K1 O2 112.80(8) . . ?
O4 K1 O6 110.64(8) . . ?
O2 K1 O6 112.83(8) . . ?
O4 K1 N1 90.53(8) . . ?
O2 K1 N1 143.62(8) . . ?
O6 K1 N1 81.61(8) . . ?
O4 K1 O1 137.68(8) . . ?
O2 K1 O1 57.57(7) . . ?
O6 K1 O1 55.65(7) . . ?
N1 K1 O1 121.78(8) . . ?
O4 K1 O3 56.68(8) . . ?
O2 K1 O3 56.76(7) . . ?
O6 K1 O3 139.43(8) . . ?
N1 K1 O3 131.85(8) . . ?
O1 K1 O3 105.20(8) . . ?
O4 K1 N6 134.33(8) . . ?
O2 K1 N6 102.79(8) . . ?
O6 K1 N6 78.67(7) . . ?
N1 K1 N6 45.31(7) . . ?
O1 K1 N6 85.49(7) . . ?
O3 K1 N6 139.73(7) . . ?
O4 K1 O5 56.03(7) . . ?
O2 K1 O5 140.82(8) . . ?
O6 K1 O5 55.35(7) . . ?
N1 K1 O5 75.25(7) . . ?
O1 K1 O5 103.20(7) . . ?
O3 K1 O5 105.46(7) . . ?
N6 K1 O5 109.67(7) . . ?
O4 K1 N5 70.67(7) . 3_657 ?
O2 K1 N5 100.29(7) . 3_657 ?
O6 K1 N5 141.76(8) . 3_657 ?
N1 K1 N5 60.20(7) . 3_657 ?
O1 K1 N5 147.16(7) . 3_657 ?
O3 K1 N5 75.01(7) . 3_657 ?
N6 K1 N5 75.74(7) . 3_657 ?
O5 K1 N5 108.38(7) . 3_657 ?
O4 K1 C1 111.37(8) . . ?
O2 K1 C1 122.75(8) . . ?
O6 K1 C1 82.56(7) . . ?
N1 K1 C1 22.50(7) . . ?
O1 K1 C1 106.24(8) . . ?
O3 K1 C1 137.55(8) . . ?
N6 K1 C1 23.24(7) . . ?
O5 K1 C1 94.32(7) . . ?
N5 K1 C1 63.10(7) 3_657 . ?
C2C O1 C1C 111.8(3) . . ?
C2C O1 K1 108.3(2) . . ?
C1C O1 K1 106.2(2) . . ?
C3C O2 C4C 111.7(3) . . ?
C3C O2 K1 119.1(2) . . ?
C4C O2 K1 120.4(2) . . ?
C6C O3 C5C 112.4(3) . . ?
C6C O3 K1 105.8(2) . . ?
C5C O3 K1 102.1(2) . . ?
C8C O4 C7C 113.0(3) . . ?
C8C O4 K1 121.9(2) . . ?
C7C O4 K1 122.2(2) . . ?
C9C O5 C10C 111.5(3) . . ?
C9C O5 K1 101.3(2) . . ?
C10C O5 K1 106.5(2) . . ?
C11C O6 C12C 113.2(3) . . ?
C11C O6 K1 122.2(2) . . ?
C12C O6 K1 120.3(2) . . ?
O1 C1C C12C 108.5(3) . . ?
O1 C1C H16 110.0 . . ?
C12C C1C H16 110.0 . . ?
O1 C1C H15 110.0 . . ?
C12C C1C H15 110.0 . . ?
H16 C1C H15 108.4 . . ?
O1 C2C C3C 109.3(3) . . ?
O1 C2C H17 109.8 . . ?
C3C C2C H17 109.8 . . ?
O1 C2C H3 109.8 . . ?
C3C C2C H3 109.8 . . ?
H17 C2C H3 108.3 . . ?
O2 C3C C2C 109.2(3) . . ?
O2 C3C H3CA 109.8 . . ?
C2C C3C H3CA 109.8 . . ?
O2 C3C H3CB 109.8 . . ?
C2C C3C H3CB 109.8 . . ?
H3CA C3C H3CB 108.3 . . ?
O2 C4C C5C 108.7(3) . . ?
O2 C4C H5 110.0 . . ?
C5C C4C H5 110.0 . . ?
O2 C4C H6 110.0 . . ?
C5C C4C H6 110.0 . . ?
H5 C4C H6 108.3 . . ?
O3 C5C C4C 109.0(3) . . ?
O3 C5C H1 109.9 . . ?
C4C C5C H1 109.9 . . ?
O3 C5C H7 109.9 . . ?
C4C C5C H7 109.9 . . ?
H1 C5C H7 108.3 . . ?
O3 C6C C7C 109.3(3) . . ?
O3 C6C H8 109.8 . . ?
C7C C6C H8 109.8 . . ?
O3 C6C H9 109.8 . . ?
C7C C6C H9 109.8 . . ?
H8 C6C H9 108.3 . . ?
O4 C7C C6C 109.1(3) . . ?
O4 C7C H7CA 109.9 . . ?
C6C C7C H7CA 109.9 . . ?
O4 C7C H7CB 109.9 . . ?
C6C C7C H7CB 109.9 . . ?
H7CA C7C H7CB 108.3 . . ?
O4 C8C C9C 109.2(3) . . ?
O4 C8C H8CA 109.8 . . ?
C9C C8C H8CA 109.8 . . ?
O4 C8C H8CB 109.8 . . ?
C9C C8C H8CB 109.8 . . ?
H8CA C8C H8CB 108.3 . . ?
O5 C9C C8C 109.2(3) . . ?
O5 C9C H9CA 109.8 . . ?
C8C C9C H9CA 109.8 . . ?
O5 C9C H9CB 109.8 . . ?
C8C C9C H9CB 109.8 . . ?
H9CA C9C H9CB 108.3 . . ?
O5 C10C C11C 108.4(3) . . ?
O5 C10C H14 110.0 . . ?
C11C C10C H14 110.0 . . ?
O5 C10C H2 110.0 . . ?
C11C C10C H2 110.0 . . ?
H14 C10C H2 108.4 . . ?
O6 C11C C10C 109.0(3) . . ?
O6 C11C H11A 109.9 . . ?
C10C C11C H11A 109.9 . . ?
O6 C11C H11B 109.9 . . ?
C10C C11C H11B 109.9 . . ?
H11A C11C H11B 108.3 . . ?
O6 C12C C1C 109.1(3) . . ?
O6 C12C H12A 109.9 . . ?
C1C C12C H12A 109.9 . . ?
O6 C12C H12B 109.9 . . ?
C1C C12C H12B 109.9 . . ?
H12A C12C H12B 108.3 . . ?
C1T O1T C4T 104.5(7) . . ?
O1T C1T C2T 112.0(7) . . ?
O1T C1T H1TA 109.2 . . ?
C2T C1T H1TA 109.2 . . ?
O1T C1T H1TB 109.2 . . ?
C2T C1T H1TB 109.2 . . ?
H1TA C1T H1TB 107.9 . . ?
C1T C2T C3T 102.9(6) . . ?
C1T C2T H2TA 111.2 . . ?
C3T C2T H2TA 111.2 . . ?
C1T C2T H2TB 111.2 . . ?
C3T C2T H2TB 111.2 . . ?
H2TA C2T H2TB 109.1 . . ?
C4T C3T C2T 101.9(5) . . ?
C4T C3T H24 111.4 . . ?
C2T C3T H24 111.4 . . ?
C4T C3T H22 111.4 . . ?
C2T C3T H22 111.4 . . ?
H24 C3T H22 109.3 . . ?
O1T C4T C3T 106.8(6) . . ?
O1T C4T H4TA 110.4 . . ?
C3T C4T H4TA 110.4 . . ?
O1T C4T H4TB 110.4 . . ?
C3T C4T H4TB 110.4 . . ?
H4TA C4T H4TB 108.6 . . ?

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
N2 Se1 N1 C1 1.5(2) . . . . ?
N2 Se1 N1 K1 -142.6(3) . . . . ?
N1 Se1 N2 C2 -1.8(2) . . . . ?
Se1 N1 C1 N6 -179.5(2) . . . . ?
K1 N1 C1 N6 -15.9(3) . . . . ?
Se1 N1 C1 C2 -0.9(3) . . . . ?
K1 N1 C1 C2 162.7(2) . . . . ?
Se1 N1 C1 K1 -163.6(2) . . . . ?
C3 N6 C1 N1 -179.6(3) . . . . ?
K1 N6 C1 N1 15.4(3) . . . . ?
C3 N6 C1 C2 1.8(4) . . . . ?
K1 N6 C1 C2 -163.2(3) . . . . ?
C3 N6 C1 K1 165.0(3) . . . . ?
Se1 N2 C2 N5 -178.7(2) . . . . ?
Se1 N2 C2 C1 1.6(3) . . . . ?
C4 N5 C2 N2 179.6(3) . . . . ?
K1 N5 C2 N2 -42.9(3) 3_657 . . . ?
C4 N5 C2 C1 -0.7(4) . . . . ?
K1 N5 C2 C1 136.8(3) 3_657 . . . ?
N1 C1 C2 N2 -0.5(4) . . . . ?
N6 C1 C2 N2 178.1(3) . . . . ?
K1 C1 C2 N2 72.6(9) . . . . ?
N1 C1 C2 N5 179.8(3) . . . . ?
N6 C1 C2 N5 -1.6(5) . . . . ?
K1 C1 C2 N5 -107.1(8) . . . . ?
C1 N6 C3 C4 0.1(5) . . . . ?
K1 N6 C3 C4 149.8(3) . . . . ?
C1 N6 C3 C5 -179.5(3) . . . . ?
K1 N6 C3 C5 -29.8(6) . . . . ?
C2 N5 C4 C3 2.8(5) . . . . ?
K1 N5 C4 C3 -118.0(3) 3_657 . . . ?
C2 N5 C4 C6 -175.2(3) . . . . ?
K1 N5 C4 C6 64.1(4) 3_657 . . . ?
N6 C3 C4 N5 -2.7(6) . . . . ?
C5 C3 C4 N5 176.9(3) . . . . ?
N6 C3 C4 C6 175.2(3) . . . . ?
C5 C3 C4 C6 -5.1(5) . . . . ?
C2C O1 C1C C12C -171.6(3) . . . . ?
K1 O1 C1C C12C 70.5(3) . . . . ?
C1C O1 C2C C3C -178.1(3) . . . . ?
K1 O1 C2C C3C -61.4(4) . . . . ?
C4C O2 C3C C2C 175.4(3) . . . . ?
K1 O2 C3C C2C -37.0(4) . . . . ?
O1 C2C C3C O2 67.6(4) . . . . ?
C3C O2 C4C C5C 170.4(3) . . . . ?
K1 O2 C4C C5C 23.3(4) . . . . ?
C6C O3 C5C C4C -175.8(3) . . . . ?
K1 O3 C5C C4C 71.3(3) . . . . ?
O2 C4C C5C O3 -67.2(4) . . . . ?
C5C O3 C6C C7C -175.8(3) . . . . ?
K1 O3 C6C C7C -65.2(3) . . . . ?
C8C O4 C7C C6C 171.3(3) . . . . ?
K1 O4 C7C C6C -27.6(4) . . . . ?
O3 C6C C7C O4 64.3(4) . . . . ?
C7C O4 C8C C9C -179.8(3) . . . . ?
K1 O4 C8C C9C 19.1(4) . . . . ?
C10C O5 C9C C8C -176.1(3) . . . . ?
K1 O5 C9C C8C 71.0(3) . . . . ?
O4 C8C C9C O5 -64.8(4) . . . . ?
C9C O5 C10C C11C -176.3(3) . . . . ?
K1 O5 C10C C11C -66.7(3) . . . . ?
C12C O6 C11C C10C 174.5(3) . . . . ?
K1 O6 C11C C10C -28.8(4) . . . . ?
O5 C10C C11C O6 65.5(4) . . . . ?
C11C O6 C12C C1C 178.8(3) . . . . ?
K1 O6 C12C C1C 21.6(4) . . . . ?
O1 C1C C12C O6 -62.8(4) . . . . ?
C4T O1T C1T C2T 33.7(14) . . . . ?
O1T C1T C2T C3T -18.3(14) . . . . ?
C1T C2T C3T C4T -3.6(10) . . . . ?
C1T O1T C4T C3T -34.7(11) . . . . ?
C2T C3T C4T O1T 22.9(9) . . . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.058

