# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_4
_database_code_depnum_ccdc_archive 'CCDC 1908993'
loop_
_audit_author_name
_audit_author_address
'Tobias Vollgraff'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N2 1+, H Se 1-'
_chemical_formula_sum            'C5 H10 N2 Se'
_chemical_formula_weight         177.11

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'
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                   9.1327(10)
_cell_length_b                   7.8090(5)
_cell_length_c                   10.9949(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.428(9)
_cell_angle_gamma                90
_cell_volume                     768.58(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6772
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      33.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    4.795
_shelx_estimated_absorpt_T_min   0.313
_shelx_estimated_absorpt_T_max   0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1296
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
STOE LANA, absorption correction by scaling of reflection intensities.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix Mo'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            6171
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.222
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1345
_reflns_number_gt                1082
_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       
; 
X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)
;
_computing_cell_refinement       
; 
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
; 
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area LANA 1.68.2.0 (STOE, 2016)
;
_computing_structure_solution    
'SHELXT (Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 102, 53227 Bonn, Germany)'
_computing_publication_material  
; 
'WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)'
'enCIFer (F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Appl. Cryst. 2004, 37, 335-338.)'
;
_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)+(0.0752P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1345
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.65499(6) 0.19677(6) 0.46016(4) 0.0246(2) Uani 1 1 d . . . . .
N1 N 0.2332(5) 0.4170(5) 0.3419(3) 0.0202(9) Uani 1 1 d . . . . .
N3 N 0.1345(5) 0.2900(5) 0.4796(4) 0.0202(9) Uani 1 1 d . . . . .
C2 C 0.2650(6) 0.3303(5) 0.4483(4) 0.0210(11) Uani 1 1 d . . . . .
H2 H 0.359836 0.302924 0.492550 0.025 Uiso 1 1 calc R U . . .
C5 C 0.0818(6) 0.4341(6) 0.3049(4) 0.0260(11) Uani 1 1 d . . . . .
H5 H 0.031711 0.489840 0.234061 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0192(6) 0.3545(6) 0.3908(5) 0.0246(11) Uani 1 1 d . . . . .
H4 H -0.082369 0.344960 0.390408 0.029 Uiso 1 1 calc R U . . .
C7 C 0.3471(6) 0.4901(7) 0.2799(4) 0.0267(12) Uani 1 1 d . . . . .
H7A H 0.312684 0.485058 0.191587 0.040 Uiso 1 1 calc R U . . .
H7B H 0.438101 0.425925 0.302445 0.040 Uiso 1 1 calc R U . . .
H7C H 0.365092 0.607245 0.304987 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1165(7) 0.1976(6) 0.5908(5) 0.0302(13) Uani 1 1 d . . . . .
H6A H 0.013615 0.166147 0.584034 0.045 Uiso 1 1 calc R U . . .
H6B H 0.146919 0.269587 0.662125 0.045 Uiso 1 1 calc R U . . .
H6C H 0.177185 0.096260 0.599520 0.045 Uiso 1 1 calc R U . . .
H1SE H 0.609(13) 0.07(2) 0.495(12) 0.22(6) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 H1SE 1.20(15) . ?
N1 C2 1.333(6) . ?
N1 C5 1.368(6) . ?
N1 C7 1.468(6) . ?
N3 C2 1.342(6) . ?
N3 C4 1.381(7) . ?
N3 C6 1.457(6) . ?
C2 H2 0.9300 . ?
C5 C4 1.349(7) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
C2 N1 C5 110.0(4) . . ?
C2 N1 C7 123.6(5) . . ?
C5 N1 C7 126.2(4) . . ?
C2 N3 C4 109.0(4) . . ?
C2 N3 C6 125.8(4) . . ?
C4 N3 C6 125.2(4) . . ?
N1 C2 N3 107.1(5) . . ?
N1 C2 H2 126.5 . . ?
N3 C2 H2 126.5 . . ?
C4 C5 N1 106.9(4) . . ?
C4 C5 H5 126.6 . . ?
N1 C5 H5 126.6 . . ?
C5 C4 N3 107.0(5) . . ?
C5 C4 H4 126.5 . . ?
N3 C4 H4 126.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C5 N1 C2 N3 0.5(5) . . . . ?
C7 N1 C2 N3 177.3(4) . . . . ?
C4 N3 C2 N1 -0.5(5) . . . . ?
C6 N3 C2 N1 -178.8(4) . . . . ?
C2 N1 C5 C4 -0.4(5) . . . . ?
C7 N1 C5 C4 -177.1(4) . . . . ?
N1 C5 C4 N3 0.1(5) . . . . ?
C2 N3 C4 C5 0.2(5) . . . . ?
C6 N3 C4 C5 178.6(4) . . . . ?

_refine_diff_density_max         1.222
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.140

####################################################################### 
# 
# 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 1908996'
loop_
_audit_author_name
_audit_author_address
'Tobias Vollgraff'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N2 1+, H S 1-'
_chemical_formula_sum            'C5 H10 N2 S'
_chemical_formula_weight         130.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.8528(18)
_cell_length_b                   7.7659(16)
_cell_length_c                   10.851(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.30(3)
_cell_angle_gamma                90
_cell_volume                     726.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5852
_cell_measurement_theta_min      5.84
_cell_measurement_theta_max      72.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    3.180
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2148
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
STOE LANA, absorption correction by scaling of reflection intensities.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            6362
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.834
_diffrn_reflns_theta_max         66.464
_diffrn_reflns_theta_full        66.464
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1282
_reflns_number_gt                1040
_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       
; 
X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)
;
_computing_cell_refinement       
; 
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
; 
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area LANA 1.68.2.0 (STOE, 2016)
;
_computing_structure_solution    
'SHELXT (Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 102, 53227 Bonn, Germany)'
_computing_publication_material  
; 
'WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)'
'enCIFer (F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Appl. Cryst. 2004, 37, 335-338.)'
;
_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)+(0.0648P)²+0.4306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1282
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_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
S1 S 0.65235(8) 0.19216(9) 0.46202(6) 0.0306(3) Uani 1 1 d . . . . .
N1 N 0.2311(3) 0.4165(3) 0.34751(19) 0.0255(5) Uani 1 1 d . . . . .
N3 N 0.1309(2) 0.2830(3) 0.48426(19) 0.0264(5) Uani 1 1 d . . . . .
C5 C 0.0100(3) 0.3498(3) 0.3935(3) 0.0310(6) Uani 1 1 d . . . . .
H5 H -0.097526 0.338898 0.391095 0.037 Uiso 1 1 calc R U . . .
C6 C 0.0732(3) 0.4335(4) 0.3086(2) 0.0303(6) Uani 1 1 d . . . . .
H6 H 0.018428 0.493154 0.235412 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2639(3) 0.3256(3) 0.4545(2) 0.0269(6) Uani 1 1 d . . . . .
H1 H 0.364942 0.296083 0.501498 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3461(3) 0.4915(4) 0.2862(2) 0.0315(6) Uani 1 1 d . . . . .
H7 H 0.445904 0.432962 0.316135 0.047 Uiso 1 1 calc R U . . .
H8 H 0.358155 0.614307 0.306934 0.047 Uiso 1 1 calc R U . . .
H9 H 0.311594 0.477626 0.194200 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1144(4) 0.1861(4) 0.5967(3) 0.0337(6) Uani 1 1 d . . . . .
H2 H 0.173613 0.078621 0.602256 0.051 Uiso 1 1 calc R U . . .
H3 H 0.004584 0.159591 0.590078 0.051 Uiso 1 1 calc R U . . .
H4 H 0.153952 0.255384 0.672751 0.051 Uiso 1 1 calc R U . . .
H1S H 0.603(5) 0.055(7) 0.498(4) 0.116(18) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 H1S 1.24(5) . ?
N1 C2 1.333(3) . ?
N1 C6 1.371(3) . ?
N1 C7 1.460(3) . ?
N3 C2 1.332(4) . ?
N3 C5 1.379(3) . ?
N3 C4 1.469(3) . ?
C5 C6 1.350(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C2 H1 0.9500 . ?
C7 H7 0.9800 . ?
C7 H8 0.9800 . ?
C7 H9 0.9800 . ?
C4 H2 0.9800 . ?
C4 H3 0.9800 . ?
C4 H4 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
C2 N1 C6 108.8(2) . . ?
C2 N1 C7 125.0(2) . . ?
C6 N1 C7 126.2(2) . . ?
C2 N3 C5 108.5(2) . . ?
C2 N3 C4 126.2(2) . . ?
C5 N3 C4 125.2(2) . . ?
C6 C5 N3 107.1(2) . . ?
C6 C5 H5 126.5 . . ?
N3 C5 H5 126.5 . . ?
C5 C6 N1 107.3(2) . . ?
C5 C6 H6 126.4 . . ?
N1 C6 H6 126.4 . . ?
N3 C2 N1 108.4(2) . . ?
N3 C2 H1 125.8 . . ?
N1 C2 H1 125.8 . . ?
N1 C7 H7 109.5 . . ?
N1 C7 H8 109.5 . . ?
H7 C7 H8 109.5 . . ?
N1 C7 H9 109.5 . . ?
H7 C7 H9 109.5 . . ?
H8 C7 H9 109.5 . . ?
N3 C4 H2 109.5 . . ?
N3 C4 H3 109.5 . . ?
H2 C4 H3 109.5 . . ?
N3 C4 H4 109.5 . . ?
H2 C4 H4 109.5 . . ?
H3 C4 H4 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
C2 N3 C5 C6 -0.1(3) . . . . ?
C4 N3 C5 C6 178.2(2) . . . . ?
N3 C5 C6 N1 0.3(3) . . . . ?
C2 N1 C6 C5 -0.5(3) . . . . ?
C7 N1 C6 C5 -177.9(2) . . . . ?
C5 N3 C2 N1 -0.2(3) . . . . ?
C4 N3 C2 N1 -178.5(2) . . . . ?
C6 N1 C2 N3 0.5(3) . . . . ?
C7 N1 C2 N3 177.9(2) . . . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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 1908998'
loop_
_audit_author_name
_audit_author_address
'Tobias Vollgraff'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N2 1+, C3 H9 S Si 1-'
_chemical_formula_sum            'C8 H18 N2 S Si'
_chemical_formula_weight         202.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.1442(16)
_cell_length_b                   12.800(3)
_cell_length_c                   11.871(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.35(3)
_cell_angle_gamma                90
_cell_volume                     1187.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8137
_cell_measurement_theta_min      5.20
_cell_measurement_theta_max      75.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.157
_exptl_absorpt_coefficient_mu    3.037
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4641
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
STOE LANA, absorption correction by scaling of reflection intensities.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'GeniX 3D HF Cu'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            5903
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.198
_diffrn_reflns_theta_max         66.492
_diffrn_reflns_theta_full        66.492
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2078
_reflns_number_gt                1910
_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       
; 
X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)
;
_computing_cell_refinement       
; 
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
; 
X-Area Integrate 1.71.0.0 (STOE, 2016)
X-Area LANA 1.68.2.0 (STOE, 2016)
;
_computing_structure_solution    
'SHELXT (Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 102, 53227 Bonn, Germany)'
_computing_publication_material  
; 
'WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)'
'enCIFer (F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Appl. Cryst. 2004, 37, 335-338.)'
;

_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)+(0.0808P)²+0.3065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2078
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
S1 S 1.11141(5) 0.50394(2) 0.24109(3) 0.01595(18) Uani 1 1 d . . . . .
Si1 Si 0.86073(6) 0.49594(3) 0.24957(4) 0.01482(19) Uani 1 1 d . . . . .
N1 N 0.65398(16) 0.25634(10) 0.55927(10) 0.0150(3) Uani 1 1 d . . . . .
N3 N 0.39001(15) 0.25304(10) 0.45529(10) 0.0157(3) Uani 1 1 d . . . . .
C6 C 0.61425(19) 0.35513(11) 0.51339(12) 0.0178(3) Uani 1 1 d . . . . .
H6 H 0.687403 0.412390 0.525001 0.021 Uiso 1 1 calc R U . . .
C2 C 0.51622(18) 0.19553(12) 0.52220(13) 0.0167(3) Uani 1 1 d . . . . .
H1 H 0.509592 0.125184 0.540036 0.020 Uiso 1 1 calc R U . . .
C5 C 0.44875(19) 0.35296(11) 0.44831(12) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.386440 0.408457 0.406714 0.022 Uiso 1 1 calc R U . . .
C7 C 0.82140(19) 0.22250(12) 0.63287(13) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.808474 0.159629 0.673639 0.029 Uiso 1 1 calc R U . . .
H8 H 0.869778 0.276205 0.688817 0.029 Uiso 1 1 calc R U . . .
H9 H 0.895816 0.209459 0.584452 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8175(2) 0.57503(12) 0.37195(13) 0.0219(4) Uani 1 1 d . . . . .
H10 H 0.698395 0.570044 0.368109 0.033 Uiso 1 1 calc R U . . .
H11 H 0.846606 0.646795 0.364001 0.033 Uiso 1 1 calc R U . . .
H12 H 0.885337 0.548566 0.446125 0.033 Uiso 1 1 calc R U . . .
C4 C 0.21516(19) 0.21646(13) 0.40045(14) 0.0222(4) Uani 1 1 d . . . . .
H2 H 0.218748 0.153807 0.356748 0.033 Uiso 1 1 calc R U . . .
H3 H 0.152638 0.269366 0.348493 0.033 Uiso 1 1 calc R U . . .
H4 H 0.159606 0.202243 0.460205 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7935(2) 0.35788(12) 0.26850(15) 0.0261(4) Uani 1 1 d . . . . .
H13 H 0.813131 0.314782 0.207371 0.039 Uiso 1 1 calc R U . . .
H14 H 0.674063 0.356680 0.264288 0.039 Uiso 1 1 calc R U . . .
H15 H 0.859022 0.331748 0.343483 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7058(2) 0.54851(14) 0.11275(14) 0.0282(4) Uani 1 1 d . . . . .
H16 H 0.721650 0.622552 0.108257 0.042 Uiso 1 1 calc R U . . .
H17 H 0.590854 0.534510 0.114840 0.042 Uiso 1 1 calc R U . . .
H18 H 0.725596 0.515336 0.045233 0.042 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
S1 Si1 2.0747(7) . ?
Si1 C10 1.8788(17) . ?
Si1 C9 1.8821(16) . ?
Si1 C8 1.8836(15) . ?
N1 C2 1.334(2) . ?
N1 C6 1.379(2) . ?
N1 C7 1.4627(19) . ?
N3 C2 1.330(2) . ?
N3 C5 1.376(2) . ?
N3 C4 1.4659(19) . ?
C6 C5 1.352(2) . ?
C6 H6 0.9300 . ?
C2 H1 0.9300 . ?
C5 H5 0.9300 . ?
C7 H7 0.9600 . ?
C7 H8 0.9600 . ?
C7 H9 0.9600 . ?
C8 H10 0.9600 . ?
C8 H11 0.9600 . ?
C8 H12 0.9600 . ?
C4 H2 0.9600 . ?
C4 H3 0.9600 . ?
C4 H4 0.9600 . ?
C9 H13 0.9600 . ?
C9 H14 0.9600 . ?
C9 H15 0.9600 . ?
C10 H16 0.9600 . ?
C10 H17 0.9600 . ?
C10 H18 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
C10 Si1 C9 106.99(8) . . ?
C10 Si1 C8 104.38(8) . . ?
C9 Si1 C8 106.78(7) . . ?
C10 Si1 S1 111.79(6) . . ?
C9 Si1 S1 112.05(5) . . ?
C8 Si1 S1 114.28(6) . . ?
C2 N1 C6 108.82(13) . . ?
C2 N1 C7 125.46(13) . . ?
C6 N1 C7 125.67(12) . . ?
C2 N3 C5 109.08(13) . . ?
C2 N3 C4 125.39(13) . . ?
C5 N3 C4 125.51(13) . . ?
C5 C6 N1 106.99(13) . . ?
C5 C6 H6 126.5 . . ?
N1 C6 H6 126.5 . . ?
N3 C2 N1 108.11(14) . . ?
N3 C2 H1 125.9 . . ?
N1 C2 H1 125.9 . . ?
C6 C5 N3 106.99(13) . . ?
C6 C5 H5 126.5 . . ?
N3 C5 H5 126.5 . . ?
N1 C7 H7 109.5 . . ?
N1 C7 H8 109.5 . . ?
H7 C7 H8 109.5 . . ?
N1 C7 H9 109.5 . . ?
H7 C7 H9 109.5 . . ?
H8 C7 H9 109.5 . . ?
Si1 C8 H10 109.5 . . ?
Si1 C8 H11 109.5 . . ?
H10 C8 H11 109.5 . . ?
Si1 C8 H12 109.5 . . ?
H10 C8 H12 109.5 . . ?
H11 C8 H12 109.5 . . ?
N3 C4 H2 109.5 . . ?
N3 C4 H3 109.5 . . ?
H2 C4 H3 109.5 . . ?
N3 C4 H4 109.5 . . ?
H2 C4 H4 109.5 . . ?
H3 C4 H4 109.5 . . ?
Si1 C9 H13 109.5 . . ?
Si1 C9 H14 109.5 . . ?
H13 C9 H14 109.5 . . ?
Si1 C9 H15 109.5 . . ?
H13 C9 H15 109.5 . . ?
H14 C9 H15 109.5 . . ?
Si1 C10 H16 109.5 . . ?
Si1 C10 H17 109.5 . . ?
H16 C10 H17 109.5 . . ?
Si1 C10 H18 109.5 . . ?
H16 C10 H18 109.5 . . ?
H17 C10 H18 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
C2 N1 C6 C5 0.43(15) . . . . ?
C7 N1 C6 C5 178.30(12) . . . . ?
C5 N3 C2 N1 0.61(15) . . . . ?
C4 N3 C2 N1 -177.89(12) . . . . ?
C6 N1 C2 N3 -0.65(15) . . . . ?
C7 N1 C2 N3 -178.52(12) . . . . ?
N1 C6 C5 N3 -0.06(15) . . . . ?
C2 N3 C5 C6 -0.34(15) . . . . ?
C4 N3 C5 C6 178.16(12) . . . . ?

_refine_diff_density_max         0.629
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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 1908997'
loop_
_audit_author_name
_audit_author_address
'Tobias Vollgraff'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N2 1+, C4 H9 S1 1-'
_chemical_formula_sum            'C9 H18 N2 S'
_chemical_formula_weight         186.31

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'
S S 0.1246 0.1234 '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                   8.475(2)
_cell_length_b                   8.816(2)
_cell_length_c                   15.127(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.40(3)
_cell_angle_gamma                90
_cell_volume                     1094.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9683
_cell_measurement_theta_min      2.5613
_cell_measurement_theta_max      25.7267

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.144
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            27138
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         26.043
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2162
_reflns_number_gt                2006
_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 Instrument Service v3.0.26'
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 102, 53227 Bonn, Germany)'
_computing_publication_material  
'WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)'
_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)+(0.0322P)²+0.4237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2162
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0685
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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
S1 S 0.65299(3) 0.70451(3) 0.41844(2) 0.01693(10) Uani 1 1 d . . . . .
N1 N 0.67644(11) 0.18258(11) 0.46791(6) 0.0149(2) Uani 1 1 d . . . . .
N3 N 0.86006(11) 0.32840(11) 0.54930(6) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.70946(14) 0.32465(13) 0.49587(8) 0.0159(2) Uani 1 1 d . . . . .
H1 H 0.637965 0.408859 0.480392 0.019 Uiso 1 1 calc R U . . .
C5 C 0.80877(14) 0.09264(13) 0.50564(8) 0.0182(2) Uani 1 1 d . . . . .
H6 H 0.817361 -0.013587 0.497373 0.022 Uiso 1 1 calc R U . . .
C4 C 0.92422(14) 0.18403(13) 0.55669(8) 0.0186(2) Uani 1 1 d . . . . .
H5 H 1.029394 0.154405 0.591063 0.022 Uiso 1 1 calc R U . . .
C8 C 0.53553(13) 0.66583(13) 0.30060(8) 0.0165(2) Uani 1 1 d . . . . .
C7 C 0.93975(15) 0.46293(14) 0.59724(8) 0.0205(3) Uani 1 1 d . . . . .
H2 H 0.892116 0.554340 0.564324 0.031 Uiso 1 1 calc R U . . .
H3 H 1.056544 0.459399 0.600233 0.031 Uiso 1 1 calc R U . . .
H4 H 0.923932 0.465057 0.659238 0.031 Uiso 1 1 calc R U . . .
C9 C 0.37962(14) 0.76034(15) 0.27753(8) 0.0209(3) Uani 1 1 d . . . . .
H11 H 0.319036 0.739312 0.214628 0.031 Uiso 1 1 calc R U . . .
H12 H 0.407579 0.868341 0.283787 0.031 Uiso 1 1 calc R U . . .
H13 H 0.312218 0.734030 0.319364 0.031 Uiso 1 1 calc R U . . .
C6 C 0.52317(14) 0.12899(14) 0.40831(8) 0.0202(2) Uani 1 1 d . . . . .
H8 H 0.431826 0.164964 0.431653 0.030 Uiso 1 1 calc R U . . .
H9 H 0.522864 0.017855 0.406901 0.030 Uiso 1 1 calc R U . . .
H10 H 0.512154 0.168267 0.346465 0.030 Uiso 1 1 calc R U . . .
C10 C 0.48870(16) 0.49842(14) 0.29070(9) 0.0254(3) Uani 1 1 d . . . . .
H14 H 0.425238 0.472361 0.334589 0.038 Uiso 1 1 calc R U . . .
H15 H 0.587594 0.436237 0.302554 0.038 Uiso 1 1 calc R U . . .
H16 H 0.423188 0.479148 0.228588 0.038 Uiso 1 1 calc R U . . .
C11 C 0.63708(16) 0.70548(17) 0.23306(9) 0.0303(3) Uani 1 1 d . . . . .
H17 H 0.571896 0.688682 0.170596 0.045 Uiso 1 1 calc R U . . .
H18 H 0.734228 0.640944 0.244769 0.045 Uiso 1 1 calc R U . . .
H19 H 0.670112 0.812180 0.240594 0.045 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
S1 C8 1.8445(13) . ?
N1 C2 1.3293(15) . ?
N1 C5 1.3762(15) . ?
N1 C6 1.4632(15) . ?
N3 C2 1.3305(15) . ?
N3 C4 1.3776(15) . ?
N3 C7 1.4646(15) . ?
C2 H1 0.9500 . ?
C5 C4 1.3517(17) . ?
C5 H6 0.9500 . ?
C4 H5 0.9500 . ?
C8 C10 1.5260(17) . ?
C8 C9 1.5273(16) . ?
C8 C11 1.5310(17) . ?
C7 H2 0.9800 . ?
C7 H3 0.9800 . ?
C7 H4 0.9800 . ?
C9 H11 0.9800 . ?
C9 H12 0.9800 . ?
C9 H13 0.9800 . ?
C6 H8 0.9800 . ?
C6 H9 0.9800 . ?
C6 H10 0.9800 . ?
C10 H14 0.9800 . ?
C10 H15 0.9800 . ?
C10 H16 0.9800 . ?
C11 H17 0.9800 . ?
C11 H18 0.9800 . ?
C11 H19 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
C2 N1 C5 109.00(10) . . ?
C2 N1 C6 125.78(10) . . ?
C5 N1 C6 125.21(10) . . ?
C2 N3 C4 109.03(10) . . ?
C2 N3 C7 125.14(10) . . ?
C4 N3 C7 125.72(10) . . ?
N1 C2 N3 108.12(10) . . ?
N1 C2 H1 125.9 . . ?
N3 C2 H1 125.9 . . ?
C4 C5 N1 107.04(10) . . ?
C4 C5 H6 126.5 . . ?
N1 C5 H6 126.5 . . ?
C5 C4 N3 106.81(10) . . ?
C5 C4 H5 126.6 . . ?
N3 C4 H5 126.6 . . ?
C10 C8 C9 108.43(10) . . ?
C10 C8 C11 109.32(11) . . ?
C9 C8 C11 108.71(10) . . ?
C10 C8 S1 109.78(8) . . ?
C9 C8 S1 110.39(8) . . ?
C11 C8 S1 110.17(9) . . ?
N3 C7 H2 109.5 . . ?
N3 C7 H3 109.5 . . ?
H2 C7 H3 109.5 . . ?
N3 C7 H4 109.5 . . ?
H2 C7 H4 109.5 . . ?
H3 C7 H4 109.5 . . ?
C8 C9 H11 109.5 . . ?
C8 C9 H12 109.5 . . ?
H11 C9 H12 109.5 . . ?
C8 C9 H13 109.5 . . ?
H11 C9 H13 109.5 . . ?
H12 C9 H13 109.5 . . ?
N1 C6 H8 109.5 . . ?
N1 C6 H9 109.5 . . ?
H8 C6 H9 109.5 . . ?
N1 C6 H10 109.5 . . ?
H8 C6 H10 109.5 . . ?
H9 C6 H10 109.5 . . ?
C8 C10 H14 109.5 . . ?
C8 C10 H15 109.5 . . ?
H14 C10 H15 109.5 . . ?
C8 C10 H16 109.5 . . ?
H14 C10 H16 109.5 . . ?
H15 C10 H16 109.5 . . ?
C8 C11 H17 109.5 . . ?
C8 C11 H18 109.5 . . ?
H17 C11 H18 109.5 . . ?
C8 C11 H19 109.5 . . ?
H17 C11 H19 109.5 . . ?
H18 C11 H19 109.5 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1908994'
loop_
_audit_author_name
_audit_author_address
'Tobias Vollgraff'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N2 1+, C4 H9 Se 1-'
_chemical_formula_sum            'C9 H18 N2 Se'
_chemical_formula_weight         233.21

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'
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                   7.9370(16)
_cell_length_b                   8.6020(17)
_cell_length_c                   9.0870(18)
_cell_angle_alpha                92.68(3)
_cell_angle_beta                 102.93(3)
_cell_angle_gamma                108.73(3)
_cell_volume                     567.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.5230
_cell_measurement_theta_max      25.7318

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.218
_exptl_absorpt_coefficient_mu    3.262
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5678
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            2170
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         25.778
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2170
_reflns_number_gt                2084
_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 Instrument Service v3.0.26'
_computing_cell_refinement       'APEX2 v2012.10-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'DIAMOND 4 (H. Putz, K.Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 102, 53227 Bonn, Germany)'
_computing_publication_material  
'WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.3741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2170
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.199
_refine_ls_shift/su_max          0.000
_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
C2 C 0.0087(4) 0.2090(4) 0.3125(4) 0.0140(6) Uani 1 1 d . . . . .
H2 H 0.036147 0.155814 0.396719 0.017 Uiso 1 1 calc R U . . .
C4 C -0.0034(4) 0.2971(4) 0.0871(4) 0.0172(7) Uani 1 1 d . . . . .
H4 H 0.016280 0.314127 -0.008889 0.021 Uiso 1 1 calc R U . . .
C5 C -0.1088(4) 0.3567(4) 0.1549(4) 0.0167(6) Uani 1 1 d . . . . .
H5 H -0.175839 0.422523 0.114227 0.020 Uiso 1 1 calc R U . . .
C6 C 0.1926(5) 0.1183(4) 0.1593(4) 0.0193(7) Uani 1 1 d . . . . .
H6A H 0.154062 0.009894 0.190147 0.029 Uiso 1 1 calc R U . . .
H6AB H 0.316073 0.179123 0.216380 0.029 Uiso 1 1 calc R U . . .
H6AC H 0.188009 0.108601 0.052648 0.029 Uiso 1 1 calc R U . . .
C7 C -0.1991(5) 0.3296(4) 0.4055(4) 0.0192(7) Uani 1 1 d . . . . .
H7A H -0.136761 0.317504 0.505476 0.029 Uiso 1 1 calc R U . . .
H7AB H -0.321425 0.250125 0.378014 0.029 Uiso 1 1 calc R U . . .
H7AC H -0.204987 0.439293 0.404953 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5912(4) 0.7620(4) 0.2628(4) 0.0162(6) Uani 1 1 d . . . . .
C9 C 0.4512(5) 0.5870(4) 0.2274(5) 0.0307(8) Uani 1 1 d . . . . .
H9A H 0.331411 0.591200 0.225865 0.046 Uiso 1 1 calc R U . . .
H9AB H 0.484403 0.521767 0.304311 0.046 Uiso 1 1 calc R U . . .
H9AC H 0.449679 0.537910 0.129870 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5917(5) 0.8391(5) 0.4180(4) 0.0266(8) Uani 1 1 d . . . . .
H10A H 0.613699 0.768480 0.493339 0.040 Uiso 1 1 calc R U . . .
H10B H 0.474806 0.851796 0.413047 0.040 Uiso 1 1 calc R U . . .
H10C H 0.686990 0.945578 0.445197 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5385(5) 0.8669(5) 0.1411(4) 0.0243(7) Uani 1 1 d . . . . .
H11A H 0.628537 0.976186 0.162506 0.036 Uiso 1 1 calc R U . . .
H11B H 0.420163 0.873399 0.141579 0.036 Uiso 1 1 calc R U . . .
H11C H 0.533879 0.816825 0.042970 0.036 Uiso 1 1 calc R U . . .
N1 N -0.0986(3) 0.3018(3) 0.2958(3) 0.0135(5) Uani 1 1 d . . . . .
N3 N 0.0697(4) 0.2058(3) 0.1877(3) 0.0140(5) Uani 1 1 d . . . . .
Se1 Se 0.84204(4) 0.75703(4) 0.26867(4) 0.01498(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
C2 N3 1.332(4) . ?
C2 N1 1.332(4) . ?
C2 H2 0.9300 . ?
C4 C5 1.349(5) . ?
C4 N3 1.383(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.380(4) . ?
C5 H5 0.9300 . ?
C6 N3 1.466(4) . ?
C6 H6A 0.9600 . ?
C6 H6AB 0.9600 . ?
C6 H6AC 0.9600 . ?
C7 N1 1.464(4) . ?
C7 H7A 0.9600 . ?
C7 H7AB 0.9600 . ?
C7 H7AC 0.9600 . ?
C8 C9 1.525(5) . ?
C8 C10 1.529(4) . ?
C8 C11 1.530(5) . ?
C8 Se1 1.994(3) . ?
C9 H9A 0.9600 . ?
C9 H9AB 0.9600 . ?
C9 H9AC 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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 C2 N1 108.1(3) . . ?
N3 C2 H2 125.9 . . ?
N1 C2 H2 125.9 . . ?
C5 C4 N3 106.8(3) . . ?
C5 C4 H4 126.6 . . ?
N3 C4 H4 126.6 . . ?
C4 C5 N1 107.2(3) . . ?
C4 C5 H5 126.4 . . ?
N1 C5 H5 126.4 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6AB 109.5 . . ?
H6A C6 H6AB 109.5 . . ?
N3 C6 H6AC 109.5 . . ?
H6A C6 H6AC 109.5 . . ?
H6AB C6 H6AC 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7AB 109.5 . . ?
H7A C7 H7AB 109.5 . . ?
N1 C7 H7AC 109.5 . . ?
H7A C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
C9 C8 C10 109.0(3) . . ?
C9 C8 C11 109.7(3) . . ?
C10 C8 C11 109.2(3) . . ?
C9 C8 Se1 110.4(2) . . ?
C10 C8 Se1 109.1(2) . . ?
C11 C8 Se1 109.5(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9AB 109.5 . . ?
H9A C9 H9AB 109.5 . . ?
C8 C9 H9AC 109.5 . . ?
H9A C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 N1 C5 108.9(3) . . ?
C2 N1 C7 124.9(3) . . ?
C5 N1 C7 126.1(3) . . ?
C2 N3 C4 109.0(3) . . ?
C2 N3 C6 126.0(3) . . ?
C4 N3 C6 125.1(3) . . ?

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
N3 C4 C5 N1 0.2(4) . . . . ?
N3 C2 N1 C5 1.1(3) . . . . ?
N3 C2 N1 C7 177.0(3) . . . . ?
C4 C5 N1 C2 -0.8(4) . . . . ?
C4 C5 N1 C7 -176.6(3) . . . . ?
N1 C2 N3 C4 -1.0(3) . . . . ?
N1 C2 N3 C6 179.7(3) . . . . ?
C5 C4 N3 C2 0.5(4) . . . . ?
C5 C4 N3 C6 179.8(3) . . . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1908995'
loop_
_audit_author_name
_audit_author_address
'Tobias Vollgraff'
;Philipps Universitaet Marburg
Germany
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N2 1+, C3 H9 Se Si 1-'
_chemical_formula_sum            'C8 H18 N2 Se Si'
_chemical_formula_weight         249.29

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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                   8.125(2)
_cell_length_b                   13.039(3)
_cell_length_c                   12.038(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.72(3)
_cell_angle_gamma                90
_cell_volume                     1227.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    619
_cell_measurement_theta_min      3.0073
_cell_measurement_theta_max      28.7774

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.189
_exptl_absorpt_coefficient_mu    3.116
_shelx_estimated_absorpt_T_min   0.416
_shelx_estimated_absorpt_T_max   0.590
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.59
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS Microfocus Source'
_diffrn_measurement_device_type  'D8 Quest (Bruker AXS Inc.)'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            31330
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.351
_diffrn_reflns_theta_max         25.740
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2344
_reflns_number_gt                2118
_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 Instrument Service v3.0.26'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'DIAMOND 4 (H. Putz, K. Brandenburg, Crystal Impact GbR, Kreuzherrenstr. 102, 53227 Bonn, Germany)'
_computing_publication_material  
'WinGX 2014.1 (L.J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854)'
_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)+(0.0226P)²+0.4906P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2344
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0464
_refine_ls_wR_factor_gt          0.0448
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 1.11428(2) 0.49348(2) 0.23424(2) 0.01753(6) Uani 1 1 d . . . . .
Si1 Si 0.84758(6) 0.50292(3) 0.24570(4) 0.01762(10) Uani 1 1 d . . . . .
N1 N 0.34506(15) 0.25835(9) 0.44596(10) 0.0160(3) Uani 1 1 d . . . . .
N3 N 0.60903(15) 0.25862(9) 0.54611(10) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.48448(18) 0.20056(12) 0.48182(12) 0.0175(3) Uani 1 1 d . . . . .
H2 H 0.493519 0.130048 0.464515 0.021 Uiso 1 1 calc R U . . .
C5 C 0.3817(2) 0.35587(11) 0.48990(13) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.305116 0.412397 0.478316 0.024 Uiso 1 1 calc R U . . .
C6 C 0.78495(19) 0.22538(13) 0.59890(14) 0.0236(3) Uani 1 1 d . . . . .
H6A H 0.783934 0.161704 0.641959 0.035 Uiso 1 1 calc R U . . .
H6B H 0.845823 0.278675 0.651635 0.035 Uiso 1 1 calc R U . . .
H6C H 0.842882 0.213503 0.538461 0.035 Uiso 1 1 calc R U . . .
C4 C 0.5465(2) 0.35579(11) 0.55236(13) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.608055 0.412361 0.593163 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8090(2) 0.42854(12) 0.36988(14) 0.0252(4) Uani 1 1 d . . . . .
H8A H 0.881086 0.456073 0.442592 0.038 Uiso 1 1 calc R U . . .
H8B H 0.837274 0.356212 0.362729 0.038 Uiso 1 1 calc R U . . .
H8C H 0.688441 0.434516 0.369119 0.038 Uiso 1 1 calc R U . . .
C7 C 0.17872(19) 0.22375(12) 0.37423(13) 0.0206(3) Uani 1 1 d . . . . .
H7A H 0.102933 0.209468 0.423334 0.031 Uiso 1 1 calc R U . . .
H7B H 0.193808 0.161211 0.332918 0.031 Uiso 1 1 calc R U . . .
H7C H 0.128079 0.277414 0.318432 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7811(2) 0.63928(12) 0.26033(16) 0.0308(4) Uani 1 1 d . . . . .
H9A H 0.849924 0.667679 0.333593 0.046 Uiso 1 1 calc R U . . .
H9B H 0.659927 0.641069 0.258788 0.046 Uiso 1 1 calc R U . . .
H9C H 0.798840 0.680152 0.196229 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6936(2) 0.44768(15) 0.11434(15) 0.0350(4) Uani 1 1 d . . . . .
H10A H 0.576252 0.460582 0.117748 0.053 Uiso 1 1 calc R U . . .
H10B H 0.712435 0.373606 0.111518 0.053 Uiso 1 1 calc R U . . .
H10C H 0.711649 0.479978 0.045064 0.053 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 Si1 2.2117(7) . ?
Si1 C10 1.8741(18) . ?
Si1 C8 1.8782(16) . ?
Si1 C9 1.8803(17) . ?
N1 C2 1.3313(19) . ?
N1 C5 1.3784(19) . ?
N1 C7 1.4640(19) . ?
N3 C2 1.3311(19) . ?
N3 C4 1.3750(19) . ?
N3 C6 1.4637(19) . ?
C2 H2 0.9500 . ?
C5 C4 1.346(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C4 H4 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C10 Si1 C8 104.82(8) . . ?
C10 Si1 C9 107.43(9) . . ?
C8 Si1 C9 107.44(8) . . ?
C10 Si1 Se1 111.55(7) . . ?
C8 Si1 Se1 113.49(6) . . ?
C9 Si1 Se1 111.69(6) . . ?
C2 N1 C5 108.76(13) . . ?
C2 N1 C7 125.82(13) . . ?
C5 N1 C7 125.40(12) . . ?
C2 N3 C4 108.77(13) . . ?
C2 N3 C6 125.68(13) . . ?
C4 N3 C6 125.53(13) . . ?
N3 C2 N1 108.23(14) . . ?
N3 C2 H2 125.9 . . ?
N1 C2 H2 125.9 . . ?
C4 C5 N1 106.99(13) . . ?
C4 C5 H5 126.5 . . ?
N1 C5 H5 126.5 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C4 N3 107.25(13) . . ?
C5 C4 H4 126.4 . . ?
N3 C4 H4 126.4 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C9 H9A 109.5 . . ?
Si1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Si1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10A 109.5 . . ?
Si1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Si1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.049

