# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_Sn1
_database_code_depnum_ccdc_archive 'CCDC 1859233'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N6 O4 Sn'
_chemical_formula_weight         394.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Monoclinic
_space_group_IT_number           ?
_space_group_name_H-M_alt        I2/c
_space_group_name_Hall           ?

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

_cell_length_a                   11.9805(19)
_cell_length_b                   9.1305(9)
_cell_length_c                   12.6134(13)
_cell_angle_alpha                90
_cell_angle_beta                 116.631(9)
_cell_angle_gamma                90
_cell_volume                     1233.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7217
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.101
_shelx_estimated_absorpt_T_min   0.544
_shelx_estimated_absorpt_T_max   0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_T_max  0.6
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12182
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.871
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1261
_reflns_number_gt                1151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0334P)²+1.6077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1261
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0613
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_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
Sn1 Sn 0.0000 0.85017(3) 0.2500 0.02864(12) Uani 1 2 d S T P . .
O1 O 0.1405(2) 0.6813(2) 0.30376(18) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.2509(2) 0.5170(2) 0.2609(2) 0.0366(5) Uani 1 1 d . . . . .
N1 N 0.0120(2) 0.7565(3) 0.0776(2) 0.0288(5) Uani 1 1 d . . . . .
N2 N 0.0617(3) 0.6492(3) -0.1012(2) 0.0401(7) Uani 1 1 d . . . . .
N3 N 0.2163(3) 0.5004(3) 0.0303(3) 0.0392(6) Uani 1 1 d . . . . .
H3A H 0.2291 0.4696 -0.0275 0.047 Uiso 1 1 d R U . . .
H3B H 0.2602 0.4667 0.1005 0.047 Uiso 1 1 d R U . . .
C1 C -0.0531(3) 0.8031(4) -0.0336(3) 0.0365(7) Uani 1 1 d . . . . .
H1 H -0.1157 0.8728 -0.0519 0.044 Uiso 1 1 calc R U . . .
C2 C -0.0266(3) 0.7466(4) -0.1212(3) 0.0423(8) Uani 1 1 d . . . . .
H2 H -0.0736 0.7791 -0.1986 0.051 Uiso 1 1 calc R U . . .
C3 C 0.1270(3) 0.6009(3) 0.0109(3) 0.0308(6) Uani 1 1 d . . . . .
C4 C 0.1009(3) 0.6562(3) 0.1028(3) 0.0250(6) Uani 1 1 d . . . . .
C5 C 0.1699(3) 0.6118(3) 0.2306(3) 0.0259(6) 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
Sn1 O1 2.156(2) 2 ?
Sn1 O1 2.156(2) . ?
Sn1 N1 2.400(2) . ?
Sn1 N1 2.400(2) 2 ?
O1 C5 1.293(4) . ?
O2 C5 1.226(4) . ?
N1 C4 1.331(4) . ?
N1 C1 1.332(4) . ?
N2 C2 1.318(5) . ?
N2 C3 1.346(4) . ?
N3 C3 1.347(4) . ?
N3 H3A 0.8576 . ?
N3 H3B 0.8592 . ?
C1 C2 1.380(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.421(4) . ?
C4 C5 1.501(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sn1 O1 88.66(11) 2 . ?
O1 Sn1 N1 79.36(8) 2 . ?
O1 Sn1 N1 71.03(8) . . ?
O1 Sn1 N1 71.03(8) 2 2 ?
O1 Sn1 N1 79.36(8) . 2 ?
N1 Sn1 N1 138.25(11) . 2 ?
C5 O1 Sn1 123.45(18) . . ?
C4 N1 C1 120.0(3) . . ?
C4 N1 Sn1 113.29(18) . . ?
C1 N1 Sn1 126.5(2) . . ?
C2 N2 C3 117.4(3) . . ?
C3 N3 H3A 120.0 . . ?
C3 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N1 C1 C2 119.2(3) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
N2 C2 C1 123.5(3) . . ?
N2 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
N2 C3 N3 117.0(3) . . ?
N2 C3 C4 120.2(3) . . ?
N3 C3 C4 122.8(3) . . ?
N1 C4 C3 119.6(3) . . ?
N1 C4 C5 116.1(2) . . ?
C3 C4 C5 124.3(3) . . ?
O2 C5 O1 123.7(3) . . ?
O2 C5 C4 120.3(3) . . ?
O1 C5 C4 116.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -0.3(5) . . . . ?
Sn1 N1 C1 C2 173.9(2) . . . . ?
C3 N2 C2 C1 1.5(5) . . . . ?
N1 C1 C2 N2 -0.9(5) . . . . ?
C2 N2 C3 N3 179.4(3) . . . . ?
C2 N2 C3 C4 -0.8(5) . . . . ?
C1 N1 C4 C3 0.9(4) . . . . ?
Sn1 N1 C4 C3 -174.1(2) . . . . ?
C1 N1 C4 C5 179.4(3) . . . . ?
Sn1 N1 C4 C5 4.4(3) . . . . ?
N2 C3 C4 N1 -0.3(4) . . . . ?
N3 C3 C4 N1 179.4(3) . . . . ?
N2 C3 C4 C5 -178.7(3) . . . . ?
N3 C3 C4 C5 1.1(5) . . . . ?
Sn1 O1 C5 O2 179.0(2) . . . . ?
Sn1 O1 C5 C4 0.6(3) . . . . ?
N1 C4 C5 O2 178.0(3) . . . . ?
C3 C4 C5 O2 -3.6(4) . . . . ?
N1 C4 C5 O1 -3.6(4) . . . . ?
C3 C4 C5 O1 174.8(3) . . . . ?

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
N3 H3A O1 0.86 2.35 3.068(3) 141.4 6_565
N3 H3B O2 0.86 2.13 2.752(4) 129.4 .
C1 H1 O2 0.93 2.55 3.254(4) 133.3 3_454

_refine_diff_density_max         0.980
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.112

_shelxl_version_number           2014-3

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

data_Sn2
_database_code_depnum_ccdc_archive 'CCDC 1859234'
_audit_update_record             
;
2018-07-30 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N6 O4 Sn'
_chemical_formula_weight         394.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.2366(4)
_cell_length_b                   9.4181(4)
_cell_length_c                   16.5098(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.057(2)
_cell_angle_gamma                90
_cell_volume                     1261.04(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5487
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    2.055
_shelx_estimated_absorpt_T_min   0.578
_shelx_estimated_absorpt_T_max   0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_T_max  0.6
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25306
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2594
_reflns_number_gt                2028
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0339P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2594
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
Sn1 Sn 0.33844(3) 0.31441(2) 0.27892(2) 0.03189(9) Uani 1 1 d . . . . .
O1 O 0.2358(3) 0.4757(3) 0.34568(14) 0.0392(6) Uani 1 1 d . . . . .
O2 O 0.2654(3) 0.6456(3) 0.44028(16) 0.0430(6) Uani 1 1 d . . . . .
N5 N -0.1432(3) 0.5669(3) 0.09134(18) 0.0366(7) Uani 1 1 d . . . . .
O3 O 0.4194(3) 0.4501(3) 0.19038(14) 0.0390(6) Uani 1 1 d . . . . .
O4 O 0.3714(3) 0.6117(3) 0.09209(17) 0.0497(7) Uani 1 1 d . . . . .
N1 N 0.5578(3) 0.4507(3) 0.35493(15) 0.0293(6) Uani 1 1 d . . . . .
C1 C 0.7184(4) 0.4383(4) 0.3527(2) 0.0343(8) Uani 1 1 d . . . . .
H1 H 0.7557 0.3645 0.3233 0.041 Uiso 1 1 calc R U . . .
N4 N 0.1001(3) 0.4029(3) 0.18300(16) 0.0309(6) Uani 1 1 d . . . . .
C2 C 0.8284(4) 0.5339(4) 0.3937(2) 0.0383(8) Uani 1 1 d . . . . .
H2 H 0.9394 0.5244 0.3902 0.046 Uiso 1 1 calc R U . . .
N2 N 0.7839(3) 0.6393(3) 0.43809(18) 0.0354(7) Uani 1 1 d . . . . .
C3 C 0.6220(4) 0.6508(3) 0.4436(2) 0.0290(7) Uani 1 1 d . . . . .
C4 C 0.5068(4) 0.5551(3) 0.39844(19) 0.0272(7) Uani 1 1 d . . . . .
C5 C 0.3241(4) 0.5613(4) 0.39618(19) 0.0295(7) Uani 1 1 d . . . . .
N3 N 0.5805(4) 0.7529(3) 0.49146(19) 0.0408(7) Uani 1 1 d . . . . .
H3A H 0.6550 0.8083 0.5173 0.049 Uiso 1 1 calc R U . . .
H3B H 0.4791 0.7637 0.4966 0.049 Uiso 1 1 calc R U . . .
C6 C -0.0583(4) 0.3755(4) 0.1824(2) 0.0375(8) Uani 1 1 d . . . . .
H6 H -0.0884 0.2990 0.2122 0.045 Uiso 1 1 calc R U . . .
C7 C -0.1783(4) 0.4605(4) 0.1376(2) 0.0396(8) Uani 1 1 d . . . . .
H7 H -0.2882 0.4421 0.1402 0.047 Uiso 1 1 calc R U . . .
C8 C 0.0172(4) 0.5890(3) 0.0868(2) 0.0298(7) Uani 1 1 d . . . . .
C9 C 0.1417(4) 0.5062(3) 0.13555(19) 0.0277(7) Uani 1 1 d . . . . .
C10 C 0.3222(4) 0.5265(4) 0.1377(2) 0.0317(7) Uani 1 1 d . . . . .
N6 N 0.0509(4) 0.6914(3) 0.03654(19) 0.0407(7) Uani 1 1 d . . . . .
H6A H -0.0278 0.7402 0.0086 0.049 Uiso 1 1 calc R U . . .
H6B H 0.1515 0.7087 0.0320 0.049 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
Sn1 O3 2.134(2) . ?
Sn1 O1 2.136(2) . ?
Sn1 N1 2.386(3) . ?
Sn1 N4 2.443(3) . ?
O1 C5 1.289(4) . ?
O2 C5 1.232(4) . ?
N5 C7 1.322(5) . ?
N5 C8 1.352(4) . ?
O3 C10 1.293(4) . ?
O4 C10 1.218(4) . ?
N1 C4 1.328(4) . ?
N1 C1 1.335(4) . ?
C1 C2 1.370(5) . ?
C1 H1 0.9300 . ?
N4 C6 1.328(4) . ?
N4 C9 1.331(4) . ?
C2 N2 1.323(4) . ?
C2 H2 0.9300 . ?
N2 C3 1.357(4) . ?
C3 N3 1.327(4) . ?
C3 C4 1.422(4) . ?
C4 C5 1.500(4) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C6 C7 1.382(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N6 1.334(4) . ?
C8 C9 1.421(4) . ?
C9 C10 1.493(4) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?

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
O3 Sn1 O1 97.29(10) . . ?
O3 Sn1 N1 74.92(9) . . ?
O1 Sn1 N1 71.20(9) . . ?
O3 Sn1 N4 70.35(9) . . ?
O1 Sn1 N4 75.30(9) . . ?
N1 Sn1 N4 127.32(9) . . ?
C5 O1 Sn1 123.3(2) . . ?
C7 N5 C8 117.5(3) . . ?
C10 O3 Sn1 124.2(2) . . ?
C4 N1 C1 119.2(3) . . ?
C4 N1 Sn1 113.6(2) . . ?
C1 N1 Sn1 127.0(2) . . ?
N1 C1 C2 120.1(3) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C6 N4 C9 119.4(3) . . ?
C6 N4 Sn1 128.0(2) . . ?
C9 N4 Sn1 111.7(2) . . ?
N2 C2 C1 122.9(3) . . ?
N2 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C2 N2 C3 117.9(3) . . ?
N3 C3 N2 117.1(3) . . ?
N3 C3 C4 123.6(3) . . ?
N2 C3 C4 119.2(3) . . ?
N1 C4 C3 120.5(3) . . ?
N1 C4 C5 115.2(3) . . ?
C3 C4 C5 124.3(3) . . ?
O2 C5 O1 123.4(3) . . ?
O2 C5 C4 120.4(3) . . ?
O1 C5 C4 116.2(3) . . ?
C3 N3 H3A 120.0 . . ?
C3 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N4 C6 C7 120.1(3) . . ?
N4 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N5 C7 C6 122.7(3) . . ?
N5 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
N6 C8 N5 117.2(3) . . ?
N6 C8 C9 122.8(3) . . ?
N5 C8 C9 120.0(3) . . ?
N4 C9 C8 120.0(3) . . ?
N4 C9 C10 115.9(3) . . ?
C8 C9 C10 124.1(3) . . ?
O4 C10 O3 123.3(3) . . ?
O4 C10 C9 120.5(3) . . ?
O3 C10 C9 116.3(3) . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?

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
C4 N1 C1 C2 -1.2(5) . . . . ?
Sn1 N1 C1 C2 173.4(2) . . . . ?
N1 C1 C2 N2 1.5(6) . . . . ?
C1 C2 N2 C3 0.9(5) . . . . ?
C2 N2 C3 N3 176.9(3) . . . . ?
C2 N2 C3 C4 -3.4(5) . . . . ?
C1 N1 C4 C3 -1.3(5) . . . . ?
Sn1 N1 C4 C3 -176.6(2) . . . . ?
C1 N1 C4 C5 179.2(3) . . . . ?
Sn1 N1 C4 C5 3.9(3) . . . . ?
N3 C3 C4 N1 -176.6(3) . . . . ?
N2 C3 C4 N1 3.7(5) . . . . ?
N3 C3 C4 C5 2.8(5) . . . . ?
N2 C3 C4 C5 -176.9(3) . . . . ?
Sn1 O1 C5 O2 -173.1(2) . . . . ?
Sn1 O1 C5 C4 7.5(4) . . . . ?
N1 C4 C5 O2 173.3(3) . . . . ?
C3 C4 C5 O2 -6.1(5) . . . . ?
N1 C4 C5 O1 -7.4(4) . . . . ?
C3 C4 C5 O1 173.2(3) . . . . ?
C9 N4 C6 C7 -4.8(5) . . . . ?
Sn1 N4 C6 C7 163.7(3) . . . . ?
C8 N5 C7 C6 1.8(5) . . . . ?
N4 C6 C7 N5 3.0(6) . . . . ?
C7 N5 C8 N6 176.4(3) . . . . ?
C7 N5 C8 C9 -4.6(5) . . . . ?
C6 N4 C9 C8 2.0(5) . . . . ?
Sn1 N4 C9 C8 -168.3(2) . . . . ?
C6 N4 C9 C10 -177.9(3) . . . . ?
Sn1 N4 C9 C10 11.8(3) . . . . ?
N6 C8 C9 N4 -178.2(3) . . . . ?
N5 C8 C9 N4 2.8(5) . . . . ?
N6 C8 C9 C10 1.7(5) . . . . ?
N5 C8 C9 C10 -177.3(3) . . . . ?
Sn1 O3 C10 O4 174.0(3) . . . . ?
Sn1 O3 C10 C9 -5.6(4) . . . . ?
N4 C9 C10 O4 174.8(3) . . . . ?
C8 C9 C10 O4 -5.1(5) . . . . ?
N4 C9 C10 O3 -5.6(4) . . . . ?
C8 C9 C10 O3 174.5(3) . . . . ?

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
N3 H3A N5 0.86 2.22 3.077(4) 174.4 4_676
N3 H3B O2 0.86 2.15 2.775(4) 129.2 .
N3 H3B O4 0.86 2.27 2.890(4) 129.4 4_576
N6 H6A N2 0.86 2.10 2.962(4) 178.4 4_475
N6 H6B O2 0.86 2.36 2.997(4) 131.6 4_575
N6 H6B O4 0.86 2.12 2.744(4) 129.5 .

_refine_diff_density_max         0.715
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.127

_shelxl_version_number           2014-3

