# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Compound-17
_database_code_depnum_ccdc_archive 'CCDC 1492250'
_audit_update_record             
;
2016-09-28 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 N4 S4'
_chemical_formula_sum            'C16 H24 N4 S4'
_chemical_formula_weight         400.63

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                   9.7678(7)
_cell_length_b                   8.9291(5)
_cell_length_c                   12.0069(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.007(5)
_cell_angle_gamma                90
_cell_volume                     990.12(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18427
_cell_measurement_theta_min      1.79
_cell_measurement_theta_max      29.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.486
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            13148
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         29.191
_diffrn_reflns_theta_full        25.242
_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             2679
_reflns_number_gt                2334
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL (Sheldrick, 2014)'
_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)+(0.0953P)²+0.2587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2679
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1653
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.8248(2) 0.6571(2) 0.08414(18) 0.0461(4) Uani 1 1 d . . . . .
H1A H 0.7587 0.7246 0.0289 0.055 Uiso 1 1 calc R U . . .
H1B H 0.9201 0.6704 0.0770 0.055 Uiso 1 1 calc R U . . .
C2 C 0.7759(3) 0.4979(2) 0.0529(2) 0.0508(5) Uani 1 1 d . . . . .
H2A H 0.6765 0.4877 0.0516 0.061 Uiso 1 1 calc R U . . .
H2B H 0.8352 0.4315 0.1134 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6473(2) 0.5559(2) -0.18786(19) 0.0457(4) Uani 1 1 d . . . . .
H3A H 0.5609 0.5532 -0.1648 0.055 Uiso 1 1 calc R U . . .
H3B H 0.6801 0.6589 -0.1839 0.055 Uiso 1 1 calc R U . . .
C4 C 0.6124(2) 0.4973(3) -0.31331(19) 0.0537(5) Uani 1 1 d . . . . .
H4A H 0.7018 0.4872 -0.3312 0.064 Uiso 1 1 calc R U . . .
H4B H 0.5524 0.5702 -0.3674 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4661(2) 0.6539(3) 0.33340(17) 0.0477(4) Uani 1 1 d . . . . .
H5B H 0.4075 0.7267 0.2783 0.057 Uiso 1 1 calc R U . . .
H5A H 0.4776 0.6888 0.4125 0.057 Uiso 1 1 calc R U . . .
C6 C 0.6152(2) 0.6437(2) 0.31760(16) 0.0415(4) Uani 1 1 d . . . . .
C7 C 0.6477(2) 0.6992(2) 0.22379(17) 0.0409(4) Uani 1 1 d . . . . .
C8 C 0.7262(2) 0.5710(2) 0.40980(16) 0.0417(4) Uani 1 1 d . . . . .
N1 N 0.5492(2) 0.7548(2) 0.12504(17) 0.0489(4) Uani 1 1 d . . . . .
H1N H 0.462(3) 0.758(3) 0.125(3) 0.061(8) Uiso 1 1 d . . . . .
H2N H 0.584(3) 0.817(4) 0.092(3) 0.067(8) Uiso 1 1 d . . . . .
N2 N 0.8074(2) 0.5108(2) 0.48791(15) 0.0489(4) Uani 1 1 d . . . . .
S1 S 0.83147(5) 0.70500(6) 0.23269(4) 0.04787(19) Uani 1 1 d . . . . .
S2 S 0.78742(6) 0.44079(6) -0.08845(5) 0.0510(2) 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
C1 C2 1.508(3) . ?
C1 S1 1.814(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 S2 1.810(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(3) . ?
C3 S2 1.8141(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.533(3) 3_665 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.532(3) . ?
C5 C4 1.533(3) 3_665 ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C6 C7 1.359(3) . ?
C6 C8 1.429(3) . ?
C7 N1 1.355(3) . ?
C7 S1 1.764(2) . ?
C8 N2 1.146(3) . ?
N1 H1N 0.85(3) . ?
N1 H2N 0.82(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
C2 C1 S1 111.96(14) . . ?
C2 C1 H1A 109.2 . . ?
S1 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
S1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 S2 112.80(15) . . ?
C1 C2 H2A 109.0 . . ?
S2 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
S2 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 S2 109.49(15) . . ?
C4 C3 H3A 109.8 . . ?
S2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
S2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 113.41(17) . 3_665 ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 3_665 . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 3_665 . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 112.04(17) . 3_665 ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 3_665 . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 3_665 . ?
H5B C5 H5A 107.9 . . ?
C7 C6 C8 119.02(18) . . ?
C7 C6 C5 124.66(17) . . ?
C8 C6 C5 116.32(17) . . ?
N1 C7 C6 124.65(19) . . ?
N1 C7 S1 117.42(16) . . ?
C6 C7 S1 117.89(15) . . ?
N2 C8 C6 174.7(2) . . ?
C7 N1 H1N 116(2) . . ?
C7 N1 H2N 113(2) . . ?
H1N N1 H2N 124(3) . . ?
C7 S1 C1 102.90(9) . . ?
C2 S2 C3 101.14(10) . . ?

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
S1 C1 C2 S2 -173.58(11) . . . . ?
S2 C3 C4 C5 70.0(2) . . . 3_665 ?
C4 C5 C6 C7 106.5(2) 3_665 . . . ?
C4 C5 C6 C8 -73.9(2) 3_665 . . . ?
C8 C6 C7 N1 172.08(18) . . . . ?
C5 C6 C7 N1 -8.3(3) . . . . ?
C8 C6 C7 S1 -10.1(2) . . . . ?
C5 C6 C7 S1 169.47(14) . . . . ?
N1 C7 S1 C1 -39.80(17) . . . . ?
C6 C7 S1 C1 142.22(15) . . . . ?
C2 C1 S1 C7 -66.54(17) . . . . ?
C1 C2 S2 C3 -68.23(18) . . . . ?
C4 C3 S2 C2 -165.68(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A N2 0.97 2.63 3.415(3) 138.5 2_655
C1 H1B S2 0.97 2.99 3.872(2) 152.5 3_765
C4 H4A N2 0.97 2.70 3.508(3) 141.2 1_554
N1 H1N S2 0.85(3) 2.93(3) 3.621(2) 140(2) 3_665
N1 H2N N2 0.82(3) 2.38(4) 3.204(3) 174(3) 2_655

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_Compound-8
_database_code_depnum_ccdc_archive 'CCDC 1492251'
_audit_update_record             
;
2016-09-28 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 N2 S'
_chemical_formula_sum            'C6 H8 N2 S'
_chemical_formula_weight         140.20

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   15.7040(8)
_cell_length_b                   7.7645(4)
_cell_length_c                   15.7661(9)
_cell_angle_alpha                90
_cell_angle_beta                 133.640(3)
_cell_angle_gamma                90
_cell_volume                     1391.23(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10685
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.47

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.371
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            10854
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.816
_diffrn_reflns_theta_max         29.189
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1867
_reflns_number_gt                1656
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL (Sheldrick, 2014)'
_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)+(0.0548P)²+0.3965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1867
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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
C1 C -0.01554(10) 0.52543(15) 0.11414(10) 0.0213(2) Uani 1 1 d . . . . .
C2 C -0.11421(11) 0.43994(15) 0.02091(10) 0.0223(2) Uani 1 1 d . . . . .
C3 C -0.12181(12) 0.25081(16) -0.00694(12) 0.0281(3) Uani 1 1 d . . . . .
H3A H -0.1279(15) 0.238(2) -0.0729(15) 0.032(4) Uiso 1 1 d . . . . .
H3B H -0.1933(17) 0.206(2) -0.0320(16) 0.042(5) Uiso 1 1 d . . . . .
C4 C -0.01802(13) 0.14615(16) 0.09721(13) 0.0318(3) Uani 1 1 d . . . . .
H4A H -0.0213(15) 0.137(2) 0.1539(15) 0.032(4) Uiso 1 1 d . . . . .
H4B H -0.0255(16) 0.027(2) 0.0694(15) 0.039(4) Uiso 1 1 d . . . . .
C5 C 0.09793(12) 0.22445(17) 0.14970(12) 0.0308(3) Uani 1 1 d . . . . .
H5A H 0.1019(16) 0.241(2) 0.0900(16) 0.038(4) Uiso 1 1 d . . . . .
H5B H 0.1627(18) 0.156(3) 0.2108(17) 0.046(5) Uiso 1 1 d . . . . .
C6 C -0.21883(11) 0.53751(16) -0.05875(11) 0.0248(3) Uani 1 1 d . . . . .
N1 N -0.01359(10) 0.69715(14) 0.13548(10) 0.0273(2) Uani 1 1 d . . . . .
H1N H 0.0526(16) 0.736(2) 0.2049(15) 0.032(4) Uiso 1 1 d . . . . .
H2N H -0.0792(17) 0.739(2) 0.1110(15) 0.036(4) Uiso 1 1 d . . . . .
N2 N -0.30490(10) 0.61495(16) -0.12540(11) 0.0347(3) Uani 1 1 d . . . . .
S1 S 0.12310(3) 0.43027(4) 0.21769(3) 0.02845(13) 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
C1 C2 1.3632(16) . ?
C1 N1 1.3703(15) . ?
C1 S1 1.7451(12) . ?
C2 C6 1.4151(16) . ?
C2 C3 1.5137(17) . ?
C3 C4 1.5229(19) . ?
C3 H3A 0.983(17) . ?
C3 H3B 0.96(2) . ?
C4 C5 1.513(2) . ?
C4 H4A 0.933(17) . ?
C4 H4B 0.995(19) . ?
C5 S1 1.8095(14) . ?
C5 H5A 0.994(18) . ?
C5 H5B 0.94(2) . ?
C6 N2 1.1542(18) . ?
N1 H1N 0.893(18) . ?
N1 H2N 0.875(19) . ?

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 C1 N1 123.69(11) . . ?
C2 C1 S1 123.95(9) . . ?
N1 C1 S1 112.35(9) . . ?
C1 C2 C6 117.12(10) . . ?
C1 C2 C3 126.05(11) . . ?
C6 C2 C3 116.82(11) . . ?
C2 C3 C4 113.17(11) . . ?
C2 C3 H3A 109.7(10) . . ?
C4 C3 H3A 109.7(10) . . ?
C2 C3 H3B 108.0(11) . . ?
C4 C3 H3B 109.0(11) . . ?
H3A C3 H3B 107.1(15) . . ?
C5 C4 C3 111.33(11) . . ?
C5 C4 H4A 110.4(11) . . ?
C3 C4 H4A 110.5(11) . . ?
C5 C4 H4B 110.3(11) . . ?
C3 C4 H4B 107.9(10) . . ?
H4A C4 H4B 106.3(14) . . ?
C4 C5 S1 111.54(10) . . ?
C4 C5 H5A 112.0(11) . . ?
S1 C5 H5A 108.2(10) . . ?
C4 C5 H5B 112.1(12) . . ?
S1 C5 H5B 104.5(12) . . ?
H5A C5 H5B 108.2(15) . . ?
N2 C6 C2 178.70(14) . . ?
C1 N1 H1N 115.9(11) . . ?
C1 N1 H2N 115.6(12) . . ?
H1N N1 H2N 115.9(16) . . ?
C1 S1 C5 101.43(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
N1 C1 C2 C6 1.64(18) . . . . ?
S1 C1 C2 C6 -176.73(9) . . . . ?
N1 C1 C2 C3 -179.81(12) . . . . ?
S1 C1 C2 C3 1.81(19) . . . . ?
C1 C2 C3 C4 17.57(19) . . . . ?
C6 C2 C3 C4 -163.88(12) . . . . ?
C2 C3 C4 C5 -52.98(16) . . . . ?
C3 C4 C5 S1 67.45(14) . . . . ?
C2 C1 S1 C5 10.10(12) . . . . ?
N1 C1 S1 C5 -168.44(9) . . . . ?
C4 C5 S1 C1 -42.91(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N2 0.893(18) 2.290(18) 3.1668(16) 166.8(15) 8_566
N1 H2N N2 0.875(19) 2.286(19) 3.1069(16) 156.3(15) 7_465

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_Compound-9
_database_code_depnum_ccdc_archive 'CCDC 1492252'
_audit_update_record             
;
2016-09-28 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N3'
_chemical_formula_sum            'C10 H11 N3'
_chemical_formula_weight         173.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.3808(10)
_cell_length_b                   9.7356(5)
_cell_length_c                   16.4358(9)
_cell_angle_alpha                90
_cell_angle_beta                 131.088(3)
_cell_angle_gamma                90
_cell_volume                     2096.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7806
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            8890
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         29.221
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2833
_reflns_number_gt                2252
_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       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL (Sheldrick, 2014)'
_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)+(0.0728P)²+0.2260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2833
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
C1 C 0.50480(8) 0.46592(11) 0.64971(8) 0.0359(2) Uani 1 1 d . . . . .
C2 C 0.39561(8) 0.49278(12) 0.56496(8) 0.0358(2) Uani 1 1 d . . . . .
H1A H 0.3851(12) 0.5906(18) 0.5588(12) 0.058(4) Uiso 1 1 d . . . . .
H1B H 0.3572(11) 0.4552(14) 0.5856(12) 0.045(4) Uiso 1 1 d . . . . .
C3 C 0.35393(7) 0.43027(11) 0.45758(8) 0.0305(2) Uani 1 1 d . . . . .
H3A H 0.3644(9) 0.3304(15) 0.4649(10) 0.038(3) Uiso 1 1 d . . . . .
H3B H 0.3910(10) 0.4707(14) 0.4365(11) 0.039(3) Uiso 1 1 d . . . . .
C4 C 0.23886(7) 0.45838(10) 0.36521(8) 0.0283(2) Uani 1 1 d . . . . .
C5 C 0.20543(7) 0.38559(11) 0.26273(8) 0.0326(2) Uani 1 1 d . . . . .
H5A H 0.2482(10) 0.4226(14) 0.2496(11) 0.037(3) Uiso 1 1 d . . . . .
H5B H 0.2193(10) 0.2866(15) 0.2781(11) 0.042(3) Uiso 1 1 d . . . . .
C6 C 0.09249(8) 0.40618(13) 0.16556(9) 0.0411(3) Uani 1 1 d . . . . .
H6A H 0.0747(13) 0.506(2) 0.1491(15) 0.067(5) Uiso 1 1 d . . . . .
H6B H 0.0493(12) 0.3661(17) 0.1777(12) 0.054(4) Uiso 1 1 d . . . . .
C7 C 0.06322(8) 0.34287(12) 0.06806(9) 0.0417(3) Uani 1 1 d . . . . .
C8 C 0.21877(9) 0.61101(11) 0.34467(9) 0.0379(3) Uani 1 1 d . . . . .
H8A H 0.2593(11) 0.6561(16) 0.3303(12) 0.050(4) Uiso 1 1 d . . . . .
C9 C 0.15791(13) 0.68542(15) 0.34748(13) 0.0596(4) Uani 1 1 d . . . . .
H9A H 0.1146(15) 0.644(2) 0.3627(15) 0.077(5) Uiso 1 1 d . . . . .
H9B H 0.1500(16) 0.784(3) 0.3306(17) 0.096(7) Uiso 1 1 d . . . . .
C10 C 0.18161(8) 0.39973(11) 0.39430(9) 0.0347(2) Uani 1 1 d . . . . .
N1 N 0.59017(7) 0.44492(12) 0.71483(8) 0.0462(3) Uani 1 1 d . . . . .
N2 N 0.04094(9) 0.29264(13) -0.00760(9) 0.0555(3) Uani 1 1 d . . . . .
N3 N 0.13706(8) 0.35335(13) 0.41649(10) 0.0534(3) 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
C1 N1 1.1408(15) . ?
C1 C2 1.4614(15) . ?
C2 C3 1.5263(14) . ?
C2 H1A 0.962(18) . ?
C2 H1B 0.997(15) . ?
C3 C4 1.5456(13) . ?
C3 H3A 0.982(15) . ?
C3 H3B 0.991(14) . ?
C4 C10 1.4731(13) . ?
C4 C8 1.5129(14) . ?
C4 C5 1.5460(14) . ?
C5 C6 1.5242(14) . ?
C5 H5A 0.969(14) . ?
C5 H5B 0.985(15) . ?
C6 C7 1.4611(16) . ?
C6 H6A 1.01(2) . ?
C6 H6B 0.976(17) . ?
C7 N2 1.1414(17) . ?
C8 C9 1.3075(19) . ?
C8 H8A 0.981(16) . ?
C9 H9A 1.02(2) . ?
C9 H9B 0.98(2) . ?
C10 N3 1.1435(14) . ?

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 C1 C2 179.06(11) . . ?
C1 C2 C3 111.28(9) . . ?
C1 C2 H1A 108.4(9) . . ?
C3 C2 H1A 111.1(9) . . ?
C1 C2 H1B 110.5(8) . . ?
C3 C2 H1B 109.4(8) . . ?
H1A C2 H1B 106.0(13) . . ?
C2 C3 C4 112.93(8) . . ?
C2 C3 H3A 110.1(8) . . ?
C4 C3 H3A 108.2(7) . . ?
C2 C3 H3B 108.8(8) . . ?
C4 C3 H3B 107.8(8) . . ?
H3A C3 H3B 109.0(11) . . ?
C10 C4 C8 110.30(9) . . ?
C10 C4 C3 109.06(8) . . ?
C8 C4 C3 110.67(8) . . ?
C10 C4 C5 108.99(8) . . ?
C8 C4 C5 109.93(8) . . ?
C3 C4 C5 107.83(8) . . ?
C6 C5 C4 112.60(8) . . ?
C6 C5 H5A 111.4(8) . . ?
C4 C5 H5A 106.1(8) . . ?
C6 C5 H5B 109.1(8) . . ?
C4 C5 H5B 108.4(8) . . ?
H5A C5 H5B 109.0(11) . . ?
C7 C6 C5 111.97(9) . . ?
C7 C6 H6A 106.9(11) . . ?
C5 C6 H6A 111.5(10) . . ?
C7 C6 H6B 107.2(9) . . ?
C5 C6 H6B 111.5(9) . . ?
H6A C6 H6B 107.5(14) . . ?
N2 C7 C6 179.45(14) . . ?
C9 C8 C4 127.57(12) . . ?
C9 C8 H8A 119.1(9) . . ?
C4 C8 H8A 113.3(9) . . ?
C8 C9 H9A 122.2(12) . . ?
C8 C9 H9B 119.7(12) . . ?
H9A C9 H9B 117.9(17) . . ?
N3 C10 C4 179.51(13) . . ?

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
C1 C2 C3 C4 -179.07(8) . . . . ?
C2 C3 C4 C10 -59.68(11) . . . . ?
C2 C3 C4 C8 61.84(11) . . . . ?
C2 C3 C4 C5 -177.89(8) . . . . ?
C10 C4 C5 C6 61.73(11) . . . . ?
C8 C4 C5 C6 -59.28(12) . . . . ?
C3 C4 C5 C6 179.99(9) . . . . ?
C4 C5 C6 C7 177.03(9) . . . . ?
C10 C4 C8 C9 -2.11(17) . . . . ?
C3 C4 C8 C9 -122.89(14) . . . . ?
C5 C4 C8 C9 118.10(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A N2 1.01(2) 2.670(19) 3.5781(17) 150.2(14) 5_565
C6 H6B N3 0.976(17) 2.512(16) 3.3059(16) 138.3(12) 2

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.051

