# 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_2t
_database_code_depnum_ccdc_archive 'CCDC 1437412'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'2-aminocyclopent-1-enecarbothioic dithioperoxyanhydride '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 N2 S4'
_chemical_formula_weight         316.51

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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.0283(13)
_cell_length_b                   8.2692(9)
_cell_length_c                   14.3216(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.017(2)
_cell_angle_gamma                90.00
_cell_volume                     1393.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3799
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.26

_exptl_crystal_description       PLATES
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8056
_exptl_absorpt_correction_T_max  0.9549
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6151
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2624
_reflns_number_gt                2404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0593P)²+0.6527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2624
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.21823(5) 0.30382(7) 0.10263(4) 0.02823(17) Uani 1 1 d . . .
S2 S 0.37816(4) 0.05218(6) 0.04864(3) 0.02289(16) Uani 1 1 d . . .
S3 S 0.31158(4) 0.14312(7) -0.08121(3) 0.02390(16) Uani 1 1 d . . .
S4 S 0.12043(5) -0.07744(7) -0.05280(4) 0.02826(17) Uani 1 1 d . . .
N1 N 0.29079(16) 0.3147(2) 0.32116(13) 0.0279(4) Uani 1 1 d . . .
H1A H 0.2421 0.3464 0.2717 0.034 Uiso 1 1 calc R . .
H1B H 0.2873 0.3510 0.3768 0.034 Uiso 1 1 calc R . .
N2 N -0.03769(17) -0.0851(2) -0.24802(14) 0.0305(4) Uani 1 1 d . . .
H2A H -0.0301 -0.1076 -0.1884 0.037 Uiso 1 1 calc R . .
H2B H -0.0973 -0.1165 -0.2882 0.037 Uiso 1 1 calc R . .
C1 C 0.37081(17) 0.2107(2) 0.31171(14) 0.0196(4) Uani 1 1 d . . .
C2 C 0.45699(18) 0.1533(2) 0.39668(14) 0.0221(4) Uani 1 1 d . . .
H2C H 0.4202 0.0956 0.4409 0.026 Uiso 1 1 calc R . .
H2D H 0.4989 0.2439 0.4298 0.026 Uiso 1 1 calc R . .
C3 C 0.5360(2) 0.0411(3) 0.35643(15) 0.0310(5) Uani 1 1 d . . .
H3A H 0.5390 -0.0642 0.3867 0.037 Uiso 1 1 calc R . .
H3B H 0.6123 0.0856 0.3683 0.037 Uiso 1 1 calc R . .
C4 C 0.48925(18) 0.0255(3) 0.24926(14) 0.0233(4) Uani 1 1 d . . .
H4A H 0.5465 0.0557 0.2138 0.028 Uiso 1 1 calc R . .
H4B H 0.4653 -0.0847 0.2328 0.028 Uiso 1 1 calc R . .
C5 C 0.38840(17) 0.1404(2) 0.22706(14) 0.0183(4) Uani 1 1 d . . .
C6 C 0.32546(17) 0.1734(2) 0.13506(14) 0.0199(4) Uani 1 1 d . . .
C7 C 0.18246(17) 0.0338(2) -0.12479(14) 0.0201(4) Uani 1 1 d . . .
C8 C 0.14322(18) 0.0577(2) -0.22379(14) 0.0206(4) Uani 1 1 d . . .
C9 C 0.2074(2) 0.1515(3) -0.28735(14) 0.0267(5) Uani 1 1 d . . .
H9A H 0.2844 0.1111 -0.2804 0.032 Uiso 1 1 calc R . .
H9B H 0.2103 0.2657 -0.2715 0.032 Uiso 1 1 calc R . .
C10 C 0.1397(2) 0.1239(4) -0.38873(17) 0.0435(7) Uani 1 1 d . . .
H10A H 0.1207 0.2267 -0.4207 0.052 Uiso 1 1 calc R . .
H10B H 0.1844 0.0615 -0.4250 0.052 Uiso 1 1 calc R . .
C11 C 0.03202(19) 0.0327(3) -0.38189(14) 0.0279(5) Uani 1 1 d . . .
H11A H -0.0347 0.0981 -0.4060 0.034 Uiso 1 1 calc R . .
H11B H 0.0263 -0.0670 -0.4183 0.034 Uiso 1 1 calc R . .
C12 C 0.04214(19) -0.0023(2) -0.27796(14) 0.0236(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0282(3) 0.0350(3) 0.0194(3) -0.0009(2) 0.0001(2) 0.0114(2)
S2 0.0229(3) 0.0311(3) 0.0138(3) -0.00327(18) 0.0019(2) 0.0045(2)
S3 0.0233(3) 0.0331(3) 0.0148(3) 0.00034(19) 0.0027(2) -0.0049(2)
S4 0.0331(3) 0.0329(3) 0.0180(3) 0.0054(2) 0.0032(2) -0.0086(2)
N1 0.0321(11) 0.0333(10) 0.0177(9) -0.0038(7) 0.0037(8) 0.0098(8)
N2 0.0303(11) 0.0336(10) 0.0248(10) -0.0004(8) -0.0006(8) -0.0072(8)
C1 0.0197(11) 0.0212(10) 0.0171(10) -0.0011(7) 0.0022(8) -0.0019(8)
C2 0.0217(11) 0.0276(11) 0.0150(9) -0.0013(8) -0.0006(8) -0.0014(8)
C3 0.0382(14) 0.0344(12) 0.0176(10) -0.0019(8) -0.0004(10) 0.0122(10)
C4 0.0224(11) 0.0281(11) 0.0187(10) -0.0014(8) 0.0027(8) 0.0050(8)
C5 0.0170(10) 0.0203(10) 0.0165(9) -0.0006(7) 0.0013(8) -0.0011(7)
C6 0.0204(10) 0.0235(10) 0.0163(9) -0.0026(7) 0.0047(8) -0.0013(8)
C7 0.0219(11) 0.0208(10) 0.0170(9) -0.0010(7) 0.0028(8) 0.0012(8)
C8 0.0242(11) 0.0208(10) 0.0165(9) 0.0001(7) 0.0036(8) 0.0030(8)
C9 0.0291(12) 0.0334(12) 0.0177(10) 0.0034(8) 0.0055(9) 0.0028(9)
C10 0.0450(16) 0.0650(18) 0.0175(11) 0.0081(11) -0.0005(11) -0.0104(13)
C11 0.0281(12) 0.0356(12) 0.0169(10) -0.0022(9) -0.0027(9) 0.0099(9)
C12 0.0278(12) 0.0218(10) 0.0196(10) -0.0018(8) 0.0015(9) 0.0054(8)

_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 C6 1.671(2) . ?
S2 C6 1.8069(19) . ?
S2 S3 2.0112(7) . ?
S3 C7 1.793(2) . ?
S4 C7 1.669(2) . ?
N1 C1 1.319(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C12 1.321(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C1 C5 1.400(3) . ?
C1 C2 1.502(3) . ?
C2 C3 1.525(3) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.526(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.521(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.403(3) . ?
C7 C8 1.412(3) . ?
C8 C12 1.391(3) . ?
C8 C9 1.523(3) . ?
C9 C10 1.526(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.520(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.496(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S2 S3 107.28(7) . . ?
C7 S3 S2 106.41(7) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C5 127.2(2) . . ?
N1 C1 C2 121.22(18) . . ?
C5 C1 C2 111.56(17) . . ?
C1 C2 C3 105.39(16) . . ?
C1 C2 H2C 110.7 . . ?
C3 C2 H2C 110.7 . . ?
C1 C2 H2D 110.7 . . ?
C3 C2 H2D 110.7 . . ?
H2C C2 H2D 108.8 . . ?
C2 C3 C4 107.66(17) . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C5 C4 C3 105.57(16) . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
C1 C5 C6 125.70(18) . . ?
C1 C5 C4 109.63(17) . . ?
C6 C5 C4 124.65(17) . . ?
C5 C6 S1 128.37(15) . . ?
C5 C6 S2 109.75(14) . . ?
S1 C6 S2 121.88(12) . . ?
C8 C7 S4 126.77(16) . . ?
C8 C7 S3 111.29(15) . . ?
S4 C7 S3 121.94(12) . . ?
C12 C8 C7 125.51(19) . . ?
C12 C8 C9 109.95(17) . . ?
C7 C8 C9 124.53(19) . . ?
C8 C9 C10 104.86(19) . . ?
C8 C9 H9A 110.8 . . ?
C10 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C10 C9 H9B 110.8 . . ?
H9A C9 H9B 108.8 . . ?
C11 C10 C9 107.79(18) . . ?
C11 C10 H10A 110.1 . . ?
C9 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.5 . . ?
C12 C11 C10 105.44(18) . . ?
C12 C11 H11A 110.7 . . ?
C10 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
N2 C12 C8 127.9(2) . . ?
N2 C12 C11 120.6(2) . . ?
C8 C12 C11 111.51(19) . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.263
_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_H2pytz
_database_code_depnum_ccdc_archive 'CCDC 1437413'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'3, 6-di(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N6'
_chemical_formula_weight         238.26

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1982(6)
_cell_length_b                   8.2816(6)
_cell_length_c                   8.8622(6)
_cell_angle_alpha                102.040(2)
_cell_angle_beta                 111.9550(10)
_cell_angle_gamma                90.162(2)
_cell_volume                     543.61(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5487
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.44

_exptl_crystal_description       rectangular
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1
_diffrn_reflns_number            6902
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0202
_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       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2116
_reflns_number_gt                1990
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0493P)²+0.2021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.108(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2116
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23850(16) -0.01980(15) 0.56434(15) 0.0241(3) Uani 1 1 d . . .
H1 H 0.1630 -0.1111 0.5565 0.029 Uiso 1 1 calc R . .
C2 C 0.34767(16) 0.06730(15) 0.72130(15) 0.0244(3) Uani 1 1 d . . .
H2 H 0.3484 0.0357 0.8186 0.029 Uiso 1 1 calc R . .
C3 C 0.45590(16) 0.20165(15) 0.73335(15) 0.0255(3) Uani 1 1 d . . .
H3 H 0.5321 0.2647 0.8396 0.031 Uiso 1 1 calc R . .
C4 C 0.45195(15) 0.24316(15) 0.58872(15) 0.0228(3) Uani 1 1 d . . .
C5 C 0.33921(14) 0.14641(14) 0.43595(14) 0.0186(3) Uani 1 1 d . . .
C6 C 0.32976(14) 0.18254(14) 0.27593(14) 0.0185(3) Uani 1 1 d . . .
C7 C 0.21271(14) 0.28782(14) 0.00162(13) 0.0186(3) Uani 1 1 d . . .
C8 C 0.13816(15) 0.39945(14) -0.11301(14) 0.0190(3) Uani 1 1 d . . .
C9 C -0.03363(15) 0.36783(14) -0.23295(14) 0.0210(3) Uani 1 1 d . . .
C10 C -0.09536(15) 0.47883(15) -0.33398(15) 0.0231(3) Uani 1 1 d . . .
H10 H -0.2114 0.4607 -0.4177 0.028 Uiso 1 1 calc R . .
C11 C 0.01422(16) 0.61685(15) -0.31158(15) 0.0236(3) Uani 1 1 d . . .
H11 H -0.0258 0.6958 -0.3783 0.028 Uiso 1 1 calc R . .
C12 C 0.18256(16) 0.63734(15) -0.19046(16) 0.0258(3) Uani 1 1 d . . .
H12 H 0.2573 0.7320 -0.1760 0.031 Uiso 1 1 calc R . .
H4 H 0.5219(19) 0.3390(18) 0.5902(18) 0.026(3) Uiso 1 1 d . . .
H9 H -0.1031(18) 0.2697(17) -0.2437(17) 0.021(3) Uiso 1 1 d . . .
H2B H 0.1461(19) 0.0063(18) 0.1403(18) 0.026(4) Uiso 1 1 d . . .
H4B H 0.4357(18) 0.4158(17) 0.1073(17) 0.021(3) Uiso 1 1 d . . .
N1 N 0.23274(13) 0.01688(12) 0.42216(12) 0.0222(2) Uani 1 1 d . . .
N2 N 0.21611(13) 0.07883(12) 0.12647(12) 0.0204(2) Uani 1 1 d . . .
N3 N 0.11725(12) 0.16730(12) 0.00474(11) 0.0195(2) Uani 1 1 d . . .
N4 N 0.39104(12) 0.31885(13) 0.10880(12) 0.0211(2) Uani 1 1 d . . .
N5 N 0.42048(12) 0.30793(12) 0.27572(12) 0.0201(2) Uani 1 1 d . . .
N6 N 0.24628(13) 0.53063(12) -0.09199(13) 0.0236(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0274(6) 0.0235(6) 0.0239(6) 0.0070(5) 0.0117(5) -0.0003(5)
C2 0.0307(6) 0.0263(6) 0.0200(6) 0.0070(5) 0.0131(5) 0.0070(5)
C3 0.0275(6) 0.0274(6) 0.0180(6) 0.0019(5) 0.0064(5) 0.0020(5)
C4 0.0211(6) 0.0235(6) 0.0218(6) 0.0033(5) 0.0071(5) -0.0010(5)
C5 0.0170(5) 0.0200(5) 0.0195(6) 0.0048(4) 0.0075(4) 0.0042(4)
C6 0.0161(5) 0.0203(5) 0.0185(6) 0.0038(4) 0.0062(4) 0.0032(4)
C7 0.0187(5) 0.0214(6) 0.0154(5) 0.0017(4) 0.0074(4) 0.0002(4)
C8 0.0220(6) 0.0204(6) 0.0156(5) 0.0020(4) 0.0094(4) 0.0014(4)
C9 0.0219(6) 0.0221(6) 0.0189(6) 0.0028(4) 0.0086(5) -0.0008(4)
C10 0.0211(6) 0.0291(6) 0.0196(6) 0.0054(5) 0.0084(5) 0.0040(5)
C11 0.0253(6) 0.0264(6) 0.0248(6) 0.0106(5) 0.0133(5) 0.0075(5)
C12 0.0252(6) 0.0249(6) 0.0305(6) 0.0102(5) 0.0121(5) 0.0002(5)
N1 0.0234(5) 0.0229(5) 0.0204(5) 0.0057(4) 0.0081(4) 0.0005(4)
N2 0.0218(5) 0.0200(5) 0.0179(5) 0.0057(4) 0.0054(4) -0.0013(4)
N3 0.0216(5) 0.0218(5) 0.0145(5) 0.0044(4) 0.0060(4) 0.0009(4)
N4 0.0192(5) 0.0257(5) 0.0186(5) 0.0076(4) 0.0063(4) -0.0020(4)
N5 0.0184(5) 0.0248(5) 0.0173(5) 0.0069(4) 0.0058(4) 0.0021(4)
N6 0.0223(5) 0.0245(5) 0.0242(5) 0.0075(4) 0.0082(4) -0.0011(4)

_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 1.3407(15) . ?
C1 C2 1.3795(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.3823(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3838(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3917(16) . ?
C4 H4 0.973(14) . ?
C5 N1 1.3370(15) . ?
C5 C6 1.4838(15) . ?
C6 N5 1.2762(15) . ?
C6 N2 1.3994(14) . ?
C7 N3 1.2777(14) . ?
C7 N4 1.4012(14) . ?
C7 C8 1.4802(15) . ?
C8 N6 1.3368(14) . ?
C8 C9 1.3944(16) . ?
C9 C10 1.3821(16) . ?
C9 H9 0.959(14) . ?
C10 C11 1.3853(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3786(17) . ?
C11 H11 0.9500 . ?
C12 N6 1.3412(16) . ?
C12 H12 0.9500 . ?
N2 N3 1.4272(13) . ?
N2 H2B 0.887(15) . ?
N4 N5 1.4296(13) . ?
N4 H4B 0.886(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 123.80(11) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 118.32(11) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.18(11) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.34(11) . . ?
C3 C4 H4 122.5(8) . . ?
C5 C4 H4 119.1(8) . . ?
N1 C5 C4 123.22(10) . . ?
N1 C5 C6 115.55(10) . . ?
C4 C5 C6 121.23(10) . . ?
N5 C6 N2 121.14(10) . . ?
N5 C6 C5 120.35(10) . . ?
N2 C6 C5 118.49(10) . . ?
N3 C7 N4 120.57(10) . . ?
N3 C7 C8 121.21(10) . . ?
N4 C7 C8 118.21(10) . . ?
N6 C8 C9 123.34(10) . . ?
N6 C8 C7 115.33(10) . . ?
C9 C8 C7 121.33(10) . . ?
C10 C9 C8 118.16(11) . . ?
C10 C9 H9 122.7(8) . . ?
C8 C9 H9 119.1(8) . . ?
C9 C10 C11 119.11(11) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 118.67(11) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
N6 C12 C11 123.40(11) . . ?
N6 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C5 N1 C1 117.14(10) . . ?
C6 N2 N3 113.20(9) . . ?
C6 N2 H2B 113.7(9) . . ?
N3 N2 H2B 111.1(9) . . ?
C7 N3 N2 111.34(9) . . ?
C7 N4 N5 112.89(9) . . ?
C7 N4 H4B 111.0(9) . . ?
N5 N4 H4B 111.0(9) . . ?
C6 N5 N4 110.84(9) . . ?
C8 N6 C12 117.32(10) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM-Toluene'
