# 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_complex1
_database_code_depnum_ccdc_archive 'CCDC 1581688'
_audit_update_record             
;
2017-11-13 deposited with the CCDC.
2018-06-04 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         ?
_chemical_formula_sum            'C12 H22 N2 O4 S3 Sn2'
_chemical_formula_weight         591.87

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'
S S 0.1246 0.1234 '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           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                   21.3265(19)
_cell_length_b                   14.8427(14)
_cell_length_c                   10.2658(11)
_cell_angle_alpha                90
_cell_angle_beta                 116.769(3)
_cell_angle_gamma                90
_cell_volume                     2901.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1838
_cell_measurement_theta_min      2.413
_cell_measurement_theta_max      19.8435

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.949
_shelx_estimated_absorpt_T_min   0.574
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5743
_exptl_absorpt_correction_T_max  0.8756
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7314
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_full        25.015
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2566
_reflns_number_gt                1721
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)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         2566
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_restrained_S_all      0.877
_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
Sn1 Sn 0.69586(2) 0.54958(2) 0.17334(4) 0.05965(15) Uani 1 1 d . . . . .
S1 S 0.500000 0.85400(13) 0.250000 0.0912(7) Uani 1 2 d S T P . .
S2 S 0.64532(7) 0.79848(9) 0.46189(16) 0.0753(4) Uani 1 1 d . . . . .
O2 O 0.69636(15) 0.6488(2) 0.3353(3) 0.0591(8) Uani 1 1 d . . . . .
O1 O 0.69208(19) 0.5398(2) 0.4784(4) 0.0728(10) Uani 1 1 d . . . . .
N1 N 0.53524(18) 0.6883(3) 0.3027(5) 0.0704(12) Uani 1 1 d . . . . .
C4 C 0.7123(4) 0.6593(4) 0.0596(7) 0.118(2) Uani 1 1 d . . . . .
H4A H 0.667705 0.683172 -0.009118 0.177 Uiso 1 1 calc R U . . .
H4B H 0.737885 0.638986 0.008647 0.177 Uiso 1 1 calc R U . . .
H4C H 0.738574 0.705520 0.127884 0.177 Uiso 1 1 calc R U . . .
C3 C 0.6892(2) 0.6203(4) 0.4440(5) 0.0568(12) Uani 1 1 d . . . . .
C1 C 0.5598(2) 0.7683(3) 0.3372(6) 0.0662(14) Uani 1 1 d . . . . .
C2 C 0.6795(2) 0.6910(3) 0.5424(5) 0.0650(13) Uani 1 1 d . . . . .
H2A H 0.724740 0.700733 0.625914 0.078 Uiso 1 1 calc R U . . .
H2B H 0.648401 0.665970 0.578699 0.078 Uiso 1 1 calc R U . . .
C5 C 0.7880(3) 0.4787(4) 0.3152(6) 0.0894(18) Uani 1 1 d . . . . .
H5A H 0.808652 0.507354 0.409022 0.134 Uiso 1 1 calc R U . . .
H5B H 0.820891 0.478973 0.275143 0.134 Uiso 1 1 calc R U . . .
H5C H 0.775986 0.417618 0.325396 0.134 Uiso 1 1 calc R U . . .
C6 C 0.5927(3) 0.5066(4) 0.1221(7) 0.0965(19) Uani 1 1 d . . . . .
H6A H 0.566157 0.556604 0.130598 0.145 Uiso 1 1 calc R U . . .
H6B H 0.594611 0.459880 0.188480 0.145 Uiso 1 1 calc R U . . .
H6C H 0.570425 0.483919 0.024078 0.145 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 C6 2.118(5) . ?
Sn1 C4 2.123(5) . ?
Sn1 C5 2.124(5) . ?
Sn1 O2 2.217(3) . ?
Sn1 O1 2.372(3) 6_565 ?
S1 C1 1.738(5) . ?
S1 C1 1.738(5) 2_655 ?
S2 C1 1.749(5) . ?
S2 C2 1.794(5) . ?
O2 C3 1.265(5) . ?
O1 C3 1.240(5) . ?
N1 C1 1.282(5) . ?
N1 N1 1.402(7) 2_655 ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C3 C2 1.532(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 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
C6 Sn1 C4 120.3(3) . . ?
C6 Sn1 C5 123.9(3) . . ?
C4 Sn1 C5 115.3(3) . . ?
C6 Sn1 O2 92.26(18) . . ?
C4 Sn1 O2 87.50(19) . . ?
C5 Sn1 O2 97.15(17) . . ?
C6 Sn1 O1 89.16(18) . 6_565 ?
C4 Sn1 O1 85.24(18) . 6_565 ?
C5 Sn1 O1 88.31(18) . 6_565 ?
O2 Sn1 O1 172.29(11) . 6_565 ?
C1 S1 C1 85.9(3) . 2_655 ?
C1 S2 C2 100.5(2) . . ?
C3 O2 Sn1 118.6(3) . . ?
C3 O1 Sn1 139.3(3) . 6_566 ?
C1 N1 N1 112.1(3) . 2_655 ?
Sn1 C4 H4A 109.5 . . ?
Sn1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Sn1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C3 O2 124.3(4) . . ?
O1 C3 C2 118.4(4) . . ?
O2 C3 C2 117.3(4) . . ?
N1 C1 S1 114.9(4) . . ?
N1 C1 S2 127.0(4) . . ?
S1 C1 S2 118.1(3) . . ?
C3 C2 S2 116.9(3) . . ?
C3 C2 H2A 108.1 . . ?
S2 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
S2 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
Sn1 C5 H5A 109.5 . . ?
Sn1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Sn1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Sn1 C6 H6A 109.5 . . ?
Sn1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Sn1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.500 0.000 0.010 506.7 75.1
2 0.000 0.500 -0.128 506.7 75.1
_platon_squeeze_details          
;
;

_refine_diff_density_max         0.771
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_160917d
_database_code_depnum_ccdc_archive 'CCDC 1581691'
_audit_update_record             
;
2017-10-24 deposited with the CCDC.
2018-06-04 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         ?
_chemical_formula_sum            'C14 H22 N2 O4 S3 Sn'
_chemical_formula_weight         497.20

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'
O O 0.0106 0.0060 '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'
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                   8.7371(7)
_cell_length_b                   27.488(2)
_cell_length_c                   9.2680(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.127(3)
_cell_angle_gamma                90
_cell_volume                     2061.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1520
_cell_measurement_theta_min      2.5005
_cell_measurement_theta_max      25.9675

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.562
_shelx_estimated_absorpt_T_min   0.540
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5400
_exptl_absorpt_correction_T_max  0.9546
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9451
_diffrn_reflns_av_unetI/netI     0.1451
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.485
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_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             3624
_reflns_number_gt                1582
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1643P)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         3624
_refine_ls_number_parameters     219
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.1855
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.3012
_refine_ls_wR_factor_gt          0.2546
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.999
_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 0.28992(15) 0.62227(4) 0.63194(13) 0.0658(5) Uani 1 1 d . U . . .
S1 S 0.8707(6) 0.76333(16) 0.8376(5) 0.0720(12) Uani 1 1 d . . . . .
S2 S 0.5700(6) 0.77653(16) 0.5446(5) 0.0708(12) Uani 1 1 d . . . . .
S3 S 1.1192(5) 0.69387(18) 1.0514(5) 0.0761(13) Uani 1 1 d . . . . .
O1 O 0.3527(13) 0.6948(4) 0.5951(12) 0.069(3) Uani 1 1 d . U . . .
O2 O 0.3681(14) 0.6491(5) 0.4011(12) 0.078(3) Uani 1 1 d . U . . .
O3 O 1.2556(13) 0.6568(4) 0.8184(12) 0.070(3) Uani 1 1 d . U . . .
O4 O 1.1996(16) 0.5799(5) 0.8377(13) 0.092(4) Uani 1 1 d . U . . .
N1 N 0.7423(15) 0.6937(5) 0.6509(14) 0.066(4) Uani 1 1 d . . . . .
N2 N 0.8756(16) 0.6736(5) 0.7730(15) 0.068(4) Uani 1 1 d . . . . .
C1 C 0.9499(18) 0.7051(5) 0.8813(17) 0.058(4) Uani 1 1 d . . . . .
C2 C 0.7268(18) 0.7415(5) 0.6676(15) 0.054(4) Uani 1 1 d . . . . .
C3 C 0.4470(19) 0.7320(6) 0.4077(16) 0.069(5) Uani 1 1 d . . . . .
H3A H 0.352382 0.748563 0.332791 0.083 Uiso 1 1 calc R U . . .
H3B H 0.512069 0.719426 0.351223 0.083 Uiso 1 1 calc R U . . .
C4 C 0.3854(19) 0.6902(6) 0.4696(18) 0.065(4) Uani 1 1 d . . . . .
C5 C 0.518(3) 0.5872(8) 0.704(3) 0.120(4) Uani 1 1 d D U . . .
H5A H 0.534419 0.578292 0.609166 0.144 Uiso 1 1 calc R U . . .
H5B H 0.600416 0.611887 0.754255 0.144 Uiso 1 1 calc R U . . .
C6 C 0.566(3) 0.5433(8) 0.807(3) 0.153(6) Uani 1 1 d D U . . .
H6A H 0.497525 0.516170 0.753609 0.183 Uiso 1 1 calc R U . . .
H6B H 0.542968 0.549796 0.900168 0.183 Uiso 1 1 calc R U . . .
C7 C 0.748(3) 0.5285(10) 0.857(3) 0.177(7) Uani 1 1 d D U . . .
H7A H 0.815569 0.557289 0.867568 0.213 Uiso 1 1 calc R U . . .
H7B H 0.784138 0.512359 0.957623 0.213 Uiso 1 1 calc R U . . .
C8 C 0.768(4) 0.4946(12) 0.737(4) 0.227(11) Uani 1 1 d D U . . .
H8A H 0.800793 0.462971 0.781753 0.340 Uiso 1 1 calc R U . . .
H8B H 0.851021 0.507206 0.702251 0.340 Uiso 1 1 calc R U . . .
H8C H 0.664906 0.492040 0.649265 0.340 Uiso 1 1 calc R U . . .
C9 C 0.050(3) 0.6140(7) 0.459(3) 0.121(5) Uani 1 1 d D U . . .
H9A H -0.011720 0.643115 0.461243 0.145 Uiso 1 1 calc R U . . .
H9B H 0.061473 0.613430 0.359083 0.145 Uiso 1 1 calc R U . . .
C10 C -0.056(3) 0.5708(8) 0.463(2) 0.149(6) Uani 1 1 d D U . . .
H10A H -0.096457 0.575515 0.546423 0.179 Uiso 1 1 calc R U . . .
H10B H 0.011642 0.541695 0.486654 0.179 Uiso 1 1 calc R U . . .
C11 C -0.203(3) 0.5635(10) 0.309(3) 0.183(10) Uani 1 1 d D U . . .
H11A H -0.162477 0.557878 0.226866 0.219 Uiso 1 1 calc R U . . .
H11B H -0.263560 0.534656 0.317610 0.219 Uiso 1 1 calc R U . . .
C12 C -0.321(4) 0.6063(14) 0.265(5) 0.31(3) Uani 1 1 d D . . . .
H12A H -0.430271 0.595405 0.251364 0.468 Uiso 1 1 calc R U . . .
H12B H -0.323330 0.620072 0.168768 0.468 Uiso 1 1 calc R U . . .
H12C H -0.285228 0.630391 0.345293 0.468 Uiso 1 1 calc R U . . .
C13 C 1.160(2) 0.6312(6) 1.0231(18) 0.074(5) Uani 1 1 d . . . . .
H13A H 1.246922 0.619346 1.117144 0.089 Uiso 1 1 calc R U . . .
H13B H 1.061756 0.612247 1.006964 0.089 Uiso 1 1 calc R U . . .
C14 C 1.212(2) 0.6233(7) 0.8883(18) 0.073(4) Uani 1 1 d . 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 C5 2.086(19) . ?
Sn1 O3 2.089(11) 1_455 ?
Sn1 C9 2.116(19) . ?
Sn1 O1 2.130(11) . ?
Sn1 O2 2.587(11) . ?
S1 C2 1.712(15) . ?
S1 C1 1.731(15) . ?
S2 C2 1.711(15) . ?
S2 C3 1.799(16) . ?
S3 C1 1.736(15) . ?
S3 C13 1.798(18) . ?
O1 C4 1.305(18) . ?
O2 C4 1.277(18) . ?
O3 C14 1.264(19) . ?
O4 C14 1.272(19) . ?
N1 C2 1.334(19) . ?
N1 N2 1.397(16) . ?
N2 C1 1.299(17) . ?
C3 C4 1.47(2) . ?
C5 C6 1.501(10) . ?
C6 C7 1.532(10) . ?
C7 C8 1.518(10) . ?
C9 C10 1.514(10) . ?
C10 C11 1.535(10) . ?
C11 C12 1.514(10) . ?
C13 C14 1.50(2) . ?

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
C5 Sn1 O3 111.3(7) . 1_455 ?
C5 Sn1 C9 138.3(10) . . ?
O3 Sn1 C9 105.4(8) 1_455 . ?
C5 Sn1 O1 102.2(7) . . ?
O3 Sn1 O1 80.4(4) 1_455 . ?
C9 Sn1 O1 102.8(6) . . ?
C5 Sn1 O2 82.9(6) . . ?
O3 Sn1 O2 136.0(4) 1_455 . ?
C9 Sn1 O2 84.2(7) . . ?
O1 Sn1 O2 55.7(4) . . ?
C2 S1 C1 88.9(7) . . ?
C2 S2 C3 101.7(8) . . ?
C1 S3 C13 100.7(8) . . ?
C4 O1 Sn1 102.0(10) . . ?
C4 O2 Sn1 81.9(9) . . ?
C14 O3 Sn1 104.9(11) . 1_655 ?
C2 N1 N2 112.7(12) . . ?
C1 N2 N1 112.5(13) . . ?
N2 C1 S1 113.4(11) . . ?
N2 C1 S3 126.2(12) . . ?
S1 C1 S3 120.3(9) . . ?
N1 C2 S2 124.6(11) . . ?
N1 C2 S1 112.4(10) . . ?
S2 C2 S1 122.8(9) . . ?
C4 C3 S2 117.7(11) . . ?
O2 C4 O1 120.3(15) . . ?
O2 C4 C3 119.2(15) . . ?
O1 C4 C3 120.4(15) . . ?
C6 C5 Sn1 125.3(14) . . ?
C5 C6 C7 114.4(14) . . ?
C8 C7 C6 109.6(13) . . ?
C10 C9 Sn1 120.4(13) . . ?
C9 C10 C11 112.8(13) . . ?
C12 C11 C10 113.5(14) . . ?
C14 C13 S3 113.7(11) . . ?
O3 C14 O4 119.8(16) . . ?
O3 C14 C13 124.4(16) . . ?
O4 C14 C13 115.7(16) . . ?

_refine_diff_density_max         1.107
_refine_diff_density_min         -1.282
_refine_diff_density_rms         0.173

####################################################################### 
# 
# 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_161114e
_database_code_depnum_ccdc_archive 'CCDC 1581690'
_audit_update_record             
;
2017-10-24 deposited with the CCDC.
2018-06-04 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         ?
_chemical_formula_sum            'C60 H116 N4 O8 S6 Sn4'
_chemical_formula_weight         1688.68

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'
S S 0.1246 0.1234 '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      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                   10.5168(9)
_cell_length_b                   20.5001(18)
_cell_length_c                   21.9159(19)
_cell_angle_alpha                64.8960(10)
_cell_angle_beta                 78.7560(10)
_cell_angle_gamma                89.760(2)
_cell_volume                     4180.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3202
_cell_measurement_theta_min      2.3515
_cell_measurement_theta_max      18.6125

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.375
_shelx_estimated_absorpt_T_min   0.577
_shelx_estimated_absorpt_T_max   0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5766
_exptl_absorpt_correction_T_max  0.7900
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21304
_diffrn_reflns_av_unetI/netI     0.1278
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             14522
_reflns_number_gt                5349
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)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         14522
_refine_ls_number_parameters     739
_refine_ls_number_restraints     1500
_refine_ls_R_factor_all          0.1842
_refine_ls_R_factor_gt           0.0868
_refine_ls_wR_factor_ref         0.2205
_refine_ls_wR_factor_gt          0.2004
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.228
_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 0.67011(8) 0.42638(4) 0.67407(4) 0.0811(3) Uani 1 1 d . U . . .
Sn2 Sn 0.13849(8) 0.37581(5) 0.74519(5) 0.0889(3) Uani 1 1 d . U . . .
Sn3 Sn -0.13863(10) -0.12962(6) 0.80554(5) 0.1083(4) Uani 1 1 d . U . . .
Sn4 Sn 0.38172(10) -0.16014(6) 0.75955(6) 0.1135(4) Uani 1 1 d . U . . .
S1 S 0.1917(4) 0.0995(2) 0.95570(19) 0.1186(12) Uani 1 1 d . U . . .
S2 S 0.3837(4) 0.2208(2) 0.93486(18) 0.1189(12) Uani 1 1 d . U . . .
S3 S 0.1005(4) 0.0046(2) 0.8963(2) 0.1406(14) Uani 1 1 d . U . . .
S4 S -0.1035(5) 0.7224(2) 0.52010(18) 0.1322(14) Uani 1 1 d . U . . .
S5 S 0.0529(4) 0.60582(19) 0.50045(17) 0.1031(11) Uani 1 1 d . U . . .
S6 S -0.2479(5) 0.7770(3) 0.6190(2) 0.1601(17) Uani 1 1 d . U . . .
N1 N 0.3086(12) 0.1056(7) 0.8390(6) 0.123(3) Uani 1 1 d . U . . .
N2 N 0.3712(11) 0.1570(6) 0.8490(6) 0.118(3) Uani 1 1 d . U . . .
N3 N -0.0350(11) 0.6209(6) 0.6182(5) 0.106(2) Uani 1 1 d . U . . .
N4 N -0.1059(12) 0.6613(7) 0.6476(5) 0.117(3) Uani 1 1 d . U . . .
O1 O -0.0018(10) -0.0795(5) 0.8405(5) 0.136(2) Uani 1 1 d . U . . .
O2 O 0.1788(10) -0.1159(6) 0.7970(5) 0.143(2) Uani 1 1 d . U . . .
O3 O 0.2674(9) 0.3220(5) 0.8163(4) 0.118(2) Uani 1 1 d . U . . .
O4 O 0.4551(8) 0.3775(4) 0.7427(4) 0.099(2) Uani 1 1 d . U . . .
O5 O -0.0237(8) 0.4266(5) 0.6752(4) 0.103(2) Uani 1 1 d . U . . .
O6 O -0.1446(8) 0.4798(4) 0.5995(4) 0.092(2) Uani 1 1 d . U . . .
O7 O -0.4496(11) 0.7936(5) 0.7212(5) 0.135(3) Uani 1 1 d . U . . .
O8 O -0.3101(10) 0.8223(5) 0.7727(5) 0.122(3) Uani 1 1 d . U . . .
C1 C 0.2125(14) 0.0728(8) 0.8918(8) 0.115(3) Uani 1 1 d . U . . .
C2 C 0.3273(14) 0.1615(7) 0.9066(7) 0.111(3) Uani 1 1 d . U . . .
C3 C 0.1970(14) -0.0279(8) 0.8411(8) 0.132(3) Uani 1 1 d . U . . .
H3A H 0.238817 0.013072 0.798874 0.158 Uiso 1 1 calc R U . . .
H3B H 0.264953 -0.053821 0.863206 0.158 Uiso 1 1 calc R U . . .
C4 C 0.1208(17) -0.0782(9) 0.8225(9) 0.133(3) Uani 1 1 d . U . . .
C5 C -0.3032(15) -0.0888(8) 0.8550(9) 0.157(4) Uani 1 1 d D U . . .
H5A H -0.376227 -0.086888 0.833454 0.188 Uiso 1 1 calc R U . . .
H5B H -0.329733 -0.122639 0.903261 0.188 Uiso 1 1 calc R U . . .
C6 C -0.2716(14) -0.0151(8) 0.8503(9) 0.180(5) Uani 1 1 d D U . . .
H6A H -0.238168 0.016719 0.801936 0.216 Uiso 1 1 calc R U . . .
H6B H -0.200598 -0.018885 0.873674 0.216 Uiso 1 1 calc R U . . .
C7 C -0.3765(18) 0.0233(8) 0.8782(10) 0.223(7) Uani 1 1 d D U . . .
H7A H -0.337788 0.050020 0.898420 0.267 Uiso 1 1 calc R U . . .
H7B H -0.412045 0.057552 0.840488 0.267 Uiso 1 1 calc R U . . .
C8 C -0.4838(18) -0.0302(11) 0.9315(10) 0.264(9) Uani 1 1 d D U . . .
H8A H -0.548372 -0.005037 0.948249 0.396 Uiso 1 1 calc R U . . .
H8B H -0.522983 -0.056106 0.911266 0.396 Uiso 1 1 calc R U . . .
H8C H -0.448837 -0.063627 0.969111 0.396 Uiso 1 1 calc R U . . .
C9 C -0.1033(17) -0.2388(8) 0.8628(9) 0.158(4) Uani 1 1 d . U . . .
H9A H -0.088672 -0.261201 0.831157 0.190 Uiso 1 1 calc R U . . .
H9B H -0.022447 -0.238166 0.877574 0.190 Uiso 1 1 calc R U . . .
C10 C -0.199(2) -0.2858(11) 0.9227(10) 0.191(5) Uani 1 1 d . U . . .
H10A H -0.229433 -0.258122 0.948331 0.229 Uiso 1 1 calc R U . . .
H10B H -0.272505 -0.295464 0.905996 0.229 Uiso 1 1 calc R U . . .
C11 C -0.170(2) -0.3532(11) 0.9706(11) 0.217(6) Uani 1 1 d . U . . .
H11A H -0.105619 -0.345427 0.993598 0.260 Uiso 1 1 calc R U . . .
H11B H -0.133590 -0.381455 0.946479 0.260 Uiso 1 1 calc R U . . .
C12 C -0.289(2) -0.3937(12) 1.0227(12) 0.260(9) Uani 1 1 d . U . . .
H12A H -0.267682 -0.439220 1.054782 0.391 Uiso 1 1 calc R U . . .
H12B H -0.324605 -0.365963 1.046991 0.391 Uiso 1 1 calc R U . . .
H12C H -0.352529 -0.401931 0.999951 0.391 Uiso 1 1 calc R U . . .
C13 C -0.0548(17) -0.0740(9) 0.6971(7) 0.174(4) Uani 1 1 d D U . . .
H13A H 0.038023 -0.063631 0.690661 0.208 Uiso 1 1 calc R U . . .
H13B H -0.067103 -0.105157 0.675196 0.208 Uiso 1 1 calc R U . . .
C14 C -0.1148(18) -0.0047(9) 0.6633(8) 0.219(6) Uani 1 1 d D U . . .
H14A H -0.086757 0.029447 0.678968 0.263 Uiso 1 1 calc R U . . .
H14B H -0.208533 -0.014096 0.679027 0.263 Uiso 1 1 calc R U . . .
C15 C -0.0824(19) 0.0314(11) 0.5831(8) 0.252(7) Uani 1 1 d D U . . .
H15A H -0.108078 -0.001427 0.565420 0.302 Uiso 1 1 calc R U . . .
H15B H -0.126600 0.075081 0.565264 0.302 Uiso 1 1 calc R U . . .
C16 C 0.0642(19) 0.0489(13) 0.5635(10) 0.301(9) Uani 1 1 d D U . . .
H16A H 0.091858 0.071587 0.514126 0.452 Uiso 1 1 calc R U . . .
H16B H 0.087534 0.081016 0.581823 0.452 Uiso 1 1 calc R U . . .
H16C H 0.105932 0.005023 0.581979 0.452 Uiso 1 1 calc R U . . .
C17 C 0.2566(18) -0.2069(10) 0.7208(9) 0.181(4) Uani 1 1 d . U . . .
H17A H 0.238114 -0.257880 0.752081 0.217 Uiso 1 1 calc R U . . .
H17B H 0.174849 -0.184931 0.722137 0.217 Uiso 1 1 calc R U . . .
C18 C 0.302(2) -0.2010(11) 0.6522(10) 0.199(5) Uani 1 1 d . U . . .
H18A H 0.387182 -0.218901 0.648157 0.239 Uiso 1 1 calc R U . . .
H18B H 0.309160 -0.150729 0.618946 0.239 Uiso 1 1 calc R U . . .
C19 C 0.200(2) -0.2478(12) 0.6367(10) 0.223(6) Uani 1 1 d D U . . .
H19A H 0.222913 -0.296827 0.647880 0.267 Uiso 1 1 calc R U . . .
H19B H 0.110917 -0.248134 0.659251 0.267 Uiso 1 1 calc R U . . .
C20 C 0.227(2) -0.2009(12) 0.5608(10) 0.277(9) Uani 1 1 d D U . . .
H20A H 0.174232 -0.219576 0.539724 0.415 Uiso 1 1 calc R U . . .
H20B H 0.206998 -0.152561 0.552625 0.415 Uiso 1 1 calc R U . . .
H20C H 0.317323 -0.200528 0.541424 0.415 Uiso 1 1 calc R U . . .
C21 C 0.4701(17) -0.0532(8) 0.7039(8) 0.173(4) Uani 1 1 d D U . . .
H21A H 0.464145 -0.028690 0.733633 0.208 Uiso 1 1 calc R U . . .
H21B H 0.561056 -0.052841 0.683936 0.208 Uiso 1 1 calc R U . . .
C22 C 0.3928(16) -0.0166(9) 0.6471(8) 0.200(5) Uani 1 1 d D U . . .
H22A H 0.380466 -0.048113 0.625637 0.240 Uiso 1 1 calc R U . . .
H22B H 0.307815 -0.007493 0.667149 0.240 Uiso 1 1 calc R U . . .
C23 C 0.4673(19) 0.0545(10) 0.5933(9) 0.248(6) Uani 1 1 d D U . . .
H23A H 0.549029 0.045316 0.570225 0.297 Uiso 1 1 calc R U . . .
H23B H 0.486108 0.084624 0.615233 0.297 Uiso 1 1 calc R U . . .
C24 C 0.382(2) 0.0933(11) 0.5406(10) 0.281(8) Uani 1 1 d D U . . .
H24A H 0.427825 0.138298 0.506128 0.422 Uiso 1 1 calc R U . . .
H24B H 0.364634 0.063235 0.518938 0.422 Uiso 1 1 calc R U . . .
H24C H 0.301942 0.102399 0.563782 0.422 Uiso 1 1 calc R U . . .
C25 C 0.3837(19) -0.2207(10) 0.8716(9) 0.183(4) Uani 1 1 d . U . . .
H25A H 0.472021 -0.221741 0.878624 0.220 Uiso 1 1 calc R U . . .
H25B H 0.332767 -0.198111 0.897992 0.220 Uiso 1 1 calc R U . . .
C26 C 0.328(2) -0.2921(10) 0.8920(8) 0.202(5) Uani 1 1 d D U . . .
H26A H 0.379813 -0.314112 0.865393 0.242 Uiso 1 1 calc R U . . .
H26B H 0.240674 -0.290180 0.883405 0.242 Uiso 1 1 calc R U . . .
C27 C 0.323(2) -0.3367(12) 0.9680(9) 0.238(6) Uani 1 1 d D U . . .
H27A H 0.407584 -0.354518 0.974188 0.286 Uiso 1 1 calc R U . . .
H27B H 0.303656 -0.306689 0.992296 0.286 Uiso 1 1 calc R U . . .
C28 C 0.224(2) -0.3977(11) 0.9968(10) 0.268(8) Uani 1 1 d D U . . .
H28A H 0.222939 -0.425336 1.044931 0.402 Uiso 1 1 calc R U . . .
H28B H 0.140764 -0.380036 0.991213 0.402 Uiso 1 1 calc R U . . .
H28C H 0.244525 -0.427788 0.973135 0.402 Uiso 1 1 calc R U . . .
C29 C 0.4712(13) 0.2888(7) 0.8530(6) 0.112(3) Uani 1 1 d . U . . .
H29A H 0.520231 0.322698 0.861845 0.134 Uiso 1 1 calc R U . . .
H29B H 0.533626 0.265388 0.832040 0.134 Uiso 1 1 calc R U . . .
C30 C 0.3912(15) 0.3316(8) 0.8011(7) 0.103(3) Uani 1 1 d . U . . .
C31 C 0.7188(14) 0.3186(7) 0.6885(7) 0.121(3) Uani 1 1 d . U . . .
H31A H 0.807121 0.321878 0.663270 0.146 Uiso 1 1 calc R U . . .
H31B H 0.716872 0.289437 0.737004 0.146 Uiso 1 1 calc R U . . .
C32 C 0.6317(15) 0.2810(8) 0.6658(8) 0.145(4) Uani 1 1 d . U . . .
H32A H 0.618748 0.312856 0.620235 0.173 Uiso 1 1 calc R U . . .
H32B H 0.547592 0.266424 0.697531 0.173 Uiso 1 1 calc R U . . .
C33 C 0.7028(18) 0.2081(9) 0.6643(10) 0.176(5) Uani 1 1 d D U . . .
H33A H 0.765360 0.220930 0.621263 0.211 Uiso 1 1 calc R U . . .
H33B H 0.746963 0.186353 0.702277 0.211 Uiso 1 1 calc R U . . .
C34 C 0.5924(19) 0.1575(11) 0.6713(12) 0.259(9) Uani 1 1 d D U . . .
H34A H 0.625634 0.113955 0.670845 0.389 Uiso 1 1 calc R U . . .
H34B H 0.531361 0.145891 0.713938 0.389 Uiso 1 1 calc R U . . .
H34C H 0.549632 0.180232 0.633478 0.389 Uiso 1 1 calc R U . . .
C35 C 0.6970(14) 0.4663(7) 0.7443(7) 0.119(3) Uani 1 1 d . U . . .
H35A H 0.710197 0.425278 0.785333 0.142 Uiso 1 1 calc R U . . .
H35B H 0.778022 0.497065 0.724587 0.142 Uiso 1 1 calc R U . . .
C36 C 0.5974(15) 0.5077(8) 0.7677(8) 0.131(4) Uani 1 1 d . U . . .
H36A H 0.515648 0.477618 0.787724 0.157 Uiso 1 1 calc R U . . .
H36B H 0.584792 0.549749 0.727358 0.157 Uiso 1 1 calc R U . . .
C37 C 0.6270(17) 0.5344(9) 0.8213(8) 0.156(5) Uani 1 1 d . U . . .
H37A H 0.637219 0.492244 0.862235 0.187 Uiso 1 1 calc R U . . .
H37B H 0.709970 0.563385 0.801888 0.187 Uiso 1 1 calc R U . . .
C38 C 0.533(2) 0.5757(11) 0.8424(11) 0.227(8) Uani 1 1 d . U . . .
H38A H 0.561837 0.588813 0.875064 0.340 Uiso 1 1 calc R U . . .
H38B H 0.523800 0.618755 0.802923 0.340 Uiso 1 1 calc R U . . .
H38C H 0.450780 0.547351 0.863492 0.340 Uiso 1 1 calc R U . . .
C39 C 0.5630(14) 0.4885(7) 0.5951(7) 0.130(4) Uani 1 1 d . U . . .
H39A H 0.594054 0.479374 0.554978 0.156 Uiso 1 1 calc R U . . .
H39B H 0.471902 0.470413 0.612427 0.156 Uiso 1 1 calc R U . . .
C40 C 0.5727(18) 0.5712(9) 0.5716(9) 0.175(5) Uani 1 1 d . U . . .
H40A H 0.557369 0.579786 0.612583 0.211 Uiso 1 1 calc R U . . .
H40B H 0.661430 0.590121 0.547019 0.211 Uiso 1 1 calc R U . . .
C41 C 0.487(2) 0.6126(10) 0.5286(10) 0.200(6) Uani 1 1 d D U . . .
H41A H 0.396170 0.595303 0.548867 0.239 Uiso 1 1 calc R U . . .
H41B H 0.509679 0.615681 0.482356 0.239 Uiso 1 1 calc R U . . .
C42 C 0.523(2) 0.6824(11) 0.5316(12) 0.273(9) Uani 1 1 d D U . . .
H42A H 0.475149 0.719968 0.504888 0.410 Uiso 1 1 calc R U . . .
H42B H 0.503082 0.675796 0.578601 0.410 Uiso 1 1 calc R U . . .
H42C H 0.614884 0.695868 0.513089 0.410 Uiso 1 1 calc R U . . .
C43 C 0.2345(13) 0.3447(7) 0.6679(7) 0.129(3) Uani 1 1 d D U . . .
H43A H 0.256598 0.386879 0.623759 0.155 Uiso 1 1 calc R U . . .
H43B H 0.314461 0.323950 0.679403 0.155 Uiso 1 1 calc R U . . .
C44 C 0.1461(15) 0.2896(7) 0.6628(9) 0.174(4) Uani 1 1 d D U . . .
H44A H 0.057034 0.293025 0.682998 0.208 Uiso 1 1 calc R U . . .
H44B H 0.150821 0.301854 0.614516 0.208 Uiso 1 1 calc R U . . .
C45 C 0.1781(19) 0.2144(7) 0.6973(10) 0.203(5) Uani 1 1 d D U . . .
H45A H 0.178424 0.202710 0.745064 0.243 Uiso 1 1 calc R U . . .
H45B H 0.264889 0.209865 0.675208 0.243 Uiso 1 1 calc R U . . .
C46 C 0.081(2) 0.1604(9) 0.6947(11) 0.245(9) Uani 1 1 d D U . . .
H46A H 0.105152 0.112165 0.717688 0.368 Uiso 1 1 calc R U . . .
H46B H -0.004931 0.164036 0.717364 0.368 Uiso 1 1 calc R U . . .
H46C H 0.081494 0.171188 0.647541 0.368 Uiso 1 1 calc R U . . .
C47 C 0.1855(14) 0.4816(7) 0.7375(7) 0.132(3) Uani 1 1 d D U . . .
H47A H 0.275672 0.486206 0.740348 0.158 Uiso 1 1 calc R U . . .
H47B H 0.175081 0.518156 0.693130 0.158 Uiso 1 1 calc R U . . .
C48 C 0.0978(17) 0.4941(8) 0.7950(8) 0.162(4) Uani 1 1 d D U . . .
H48A H 0.008384 0.493199 0.789751 0.195 Uiso 1 1 calc R U . . .
H48B H 0.102675 0.455014 0.839106 0.195 Uiso 1 1 calc R U . . .
C49 C 0.136(2) 0.5656(10) 0.7946(9) 0.193(6) Uani 1 1 d D U . . .
H49A H 0.209541 0.560974 0.816085 0.231 Uiso 1 1 calc R U . . .
H49B H 0.159920 0.602572 0.747520 0.231 Uiso 1 1 calc R U . . .
C50 C 0.022(2) 0.5866(11) 0.8334(11) 0.254(9) Uani 1 1 d D U . . .
H50A H 0.045662 0.631825 0.833398 0.381 Uiso 1 1 calc R U . . .
H50B H -0.050322 0.591430 0.811735 0.381 Uiso 1 1 calc R U . . .
H50C H -0.000849 0.549956 0.880097 0.381 Uiso 1 1 calc R U . . .
C51 C -0.0315(14) 0.3146(8) 0.8187(7) 0.153(3) Uani 1 1 d D U . . .
H51A H -0.080866 0.347864 0.832690 0.184 Uiso 1 1 calc R U . . .
H51B H -0.083449 0.299399 0.794187 0.184 Uiso 1 1 calc R U . . .
C52 C -0.0246(14) 0.2492(8) 0.8833(8) 0.186(5) Uani 1 1 d D U . . .
H52A H 0.038559 0.261437 0.904456 0.223 Uiso 1 1 calc R U . . .
H52B H 0.009368 0.211841 0.870135 0.223 Uiso 1 1 calc R U . . .
C53 C -0.1511(17) 0.2160(10) 0.9390(8) 0.213(6) Uani 1 1 d D U . . .
H53A H -0.129193 0.182875 0.981929 0.255 Uiso 1 1 calc R U . . .
H53B H -0.195421 0.254220 0.946848 0.255 Uiso 1 1 calc R U . . .
C54 C -0.242(2) 0.1757(13) 0.9177(11) 0.327(11) Uani 1 1 d D U . . .
H54A H -0.319415 0.155841 0.953354 0.490 Uiso 1 1 calc R U . . .
H54B H -0.265285 0.208527 0.875639 0.490 Uiso 1 1 calc R U . . .
H54C H -0.199110 0.137239 0.910692 0.490 Uiso 1 1 calc R U . . .
C55 C -0.0363(14) 0.4722(8) 0.6166(7) 0.094(3) Uani 1 1 d . U . . .
C56 C 0.0841(12) 0.5195(6) 0.5651(6) 0.096(3) Uani 1 1 d . U . . .
H56A H 0.129317 0.492485 0.541597 0.116 Uiso 1 1 calc R U . . .
H56B H 0.142107 0.528530 0.590569 0.116 Uiso 1 1 calc R U . . .
C57 C -0.0280(13) 0.6433(7) 0.5551(7) 0.098(3) Uani 1 1 d . U . . .
C58 C -0.1471(15) 0.7168(8) 0.6018(7) 0.120(3) Uani 1 1 d . U . . .
C59 C -0.2375(15) 0.7567(8) 0.7044(6) 0.124(3) Uani 1 1 d . U . . .
H59A H -0.253242 0.704781 0.731923 0.149 Uiso 1 1 calc R U . . .
H59B H -0.149927 0.771084 0.704610 0.149 Uiso 1 1 calc R U . . .
C60 C -0.3355(18) 0.7946(9) 0.7384(8) 0.128(4) Uani 1 1 d . 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 C35 2.088(13) . ?
Sn1 C31 2.170(13) . ?
Sn1 C39 2.183(13) . ?
Sn1 O6 2.219(8) 1_655 ?
Sn1 O4 2.407(8) . ?
Sn2 C43 2.131(13) . ?
Sn2 C51 2.132(13) . ?
Sn2 C47 2.155(13) . ?
Sn2 O3 2.200(9) . ?
Sn2 O5 2.449(9) . ?
Sn3 C9 2.125(15) . ?
Sn3 C13 2.148(14) . ?
Sn3 O1 2.197(10) . ?
Sn3 C5 2.213(14) . ?
Sn3 O8 2.421(10) 1_545 ?
Sn4 C21 2.114(16) . ?
Sn4 C17 2.124(18) . ?
Sn4 O7 2.199(10) 1_645 ?
Sn4 C25 2.236(17) . ?
Sn4 O2 2.446(11) . ?
S1 C1 1.686(14) . ?
S1 C2 1.750(14) . ?
S2 C2 1.732(14) . ?
S2 C29 1.804(12) . ?
S3 C3 1.773(14) . ?
S3 C1 1.789(14) . ?
S4 C58 1.713(13) . ?
S4 C57 1.739(13) . ?
S5 C57 1.768(12) . ?
S5 C56 1.815(12) . ?
S6 C58 1.736(14) . ?
S6 C59 1.763(12) . ?
N1 C1 1.305(15) . ?
N1 N2 1.361(14) . ?
N2 C2 1.298(14) . ?
N3 C57 1.245(13) . ?
N3 N4 1.387(12) . ?
N4 C58 1.298(15) . ?
O1 C4 1.270(16) . ?
O2 C4 1.229(15) . ?
O3 C30 1.274(14) . ?
O4 C30 1.274(14) . ?
O5 C55 1.260(13) . ?
O6 C55 1.257(14) . ?
O7 C60 1.329(18) . ?
O8 C60 1.184(16) . ?
C3 C4 1.537(19) . ?
C5 C6 1.505(9) . ?
C6 C7 1.532(9) . ?
C7 C8 1.501(9) . ?
C9 C10 1.44(2) . ?
C10 C11 1.41(2) . ?
C11 C12 1.49(2) . ?
C13 C14 1.498(9) . ?
C14 C15 1.554(9) . ?
C15 C16 1.519(10) . ?
C17 C18 1.44(2) . ?
C18 C19 1.61(2) . ?
C19 C20 1.493(9) . ?
C21 C22 1.539(9) . ?
C22 C23 1.523(9) . ?
C23 C24 1.543(9) . ?
C25 C26 1.43(2) . ?
C26 C27 1.512(9) . ?
C27 C28 1.46(2) . ?
C29 C30 1.513(17) . ?
C31 C32 1.479(18) . ?
C32 C33 1.68(2) . ?
C33 C34 1.502(9) . ?
C35 C36 1.495(16) . ?
C36 C37 1.569(19) . ?
C37 C38 1.434(19) . ?
C39 C40 1.547(19) . ?
C40 C41 1.44(2) . ?
C41 C42 1.514(10) . ?
C43 C44 1.519(9) . ?
C44 C45 1.473(9) . ?
C45 C46 1.54(2) . ?
C47 C48 1.524(17) . ?
C48 C49 1.52(2) . ?
C49 C50 1.50(2) . ?
C51 C52 1.495(9) . ?
C52 C53 1.547(9) . ?
C53 C54 1.526(10) . ?
C55 C56 1.531(16) . ?
C59 C60 1.552(18) . ?

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
C35 Sn1 C31 121.1(6) . . ?
C35 Sn1 C39 118.1(6) . . ?
C31 Sn1 C39 120.1(6) . . ?
C35 Sn1 O6 95.2(4) . 1_655 ?
C31 Sn1 O6 93.8(4) . 1_655 ?
C39 Sn1 O6 89.4(4) . 1_655 ?
C35 Sn1 O4 88.7(4) . . ?
C31 Sn1 O4 89.8(4) . . ?
C39 Sn1 O4 83.0(4) . . ?
O6 Sn1 O4 172.4(3) 1_655 . ?
C43 Sn2 C51 121.3(6) . . ?
C43 Sn2 C47 120.1(5) . . ?
C51 Sn2 C47 117.3(6) . . ?
C43 Sn2 O3 94.2(5) . . ?
C51 Sn2 O3 92.8(5) . . ?
C47 Sn2 O3 94.3(5) . . ?
C43 Sn2 O5 88.3(4) . . ?
C51 Sn2 O5 81.2(4) . . ?
C47 Sn2 O5 89.1(5) . . ?
O3 Sn2 O5 173.9(3) . . ?
C9 Sn3 C13 120.3(6) . . ?
C9 Sn3 O1 97.3(5) . . ?
C13 Sn3 O1 97.0(6) . . ?
C9 Sn3 C5 116.1(6) . . ?
C13 Sn3 C5 121.5(6) . . ?
O1 Sn3 C5 90.1(5) . . ?
C9 Sn3 O8 86.5(5) . 1_545 ?
C13 Sn3 O8 86.2(5) . 1_545 ?
O1 Sn3 O8 172.9(3) . 1_545 ?
C5 Sn3 O8 82.8(5) . 1_545 ?
C21 Sn4 C17 123.0(7) . . ?
C21 Sn4 O7 93.2(6) . 1_645 ?
C17 Sn4 O7 91.3(6) . 1_645 ?
C21 Sn4 C25 119.6(6) . . ?
C17 Sn4 C25 116.2(7) . . ?
O7 Sn4 C25 96.5(6) 1_645 . ?
C21 Sn4 O2 90.7(5) . . ?
C17 Sn4 O2 82.0(6) . . ?
O7 Sn4 O2 173.3(4) 1_645 . ?
C25 Sn4 O2 86.3(6) . . ?
C1 S1 C2 86.5(7) . . ?
C2 S2 C29 98.9(6) . . ?
C3 S3 C1 100.9(7) . . ?
C58 S4 C57 87.3(7) . . ?
C57 S5 C56 99.5(6) . . ?
C58 S6 C59 101.6(7) . . ?
C1 N1 N2 108.6(12) . . ?
C2 N2 N1 116.3(13) . . ?
C57 N3 N4 114.6(12) . . ?
C58 N4 N3 111.6(11) . . ?
C4 O1 Sn3 122.6(11) . . ?
C4 O2 Sn4 150.1(12) . . ?
C30 O3 Sn2 125.3(9) . . ?
C30 O4 Sn1 144.4(9) . . ?
C55 O5 Sn2 142.7(9) . . ?
C55 O6 Sn1 122.6(9) . 1_455 ?
C60 O7 Sn4 122.2(9) . 1_465 ?
C60 O8 Sn3 146.1(12) . 1_565 ?
N1 C1 S1 117.5(11) . . ?
N1 C1 S3 122.5(11) . . ?
S1 C1 S3 119.9(9) . . ?
N2 C2 S2 128.0(12) . . ?
N2 C2 S1 111.0(11) . . ?
S2 C2 S1 121.0(8) . . ?
C4 C3 S3 114.3(11) . . ?
O2 C4 O1 126.1(17) . . ?
O2 C4 C3 120.2(16) . . ?
O1 C4 C3 113.4(14) . . ?
C6 C5 Sn3 113.6(10) . . ?
C5 C6 C7 120.6(11) . . ?
C8 C7 C6 110.9(11) . . ?
C10 C9 Sn3 119.8(13) . . ?
C11 C10 C9 122.0(19) . . ?
C10 C11 C12 111(2) . . ?
C14 C13 Sn3 111.9(10) . . ?
C13 C14 C15 115.9(12) . . ?
C16 C15 C14 104.6(11) . . ?
C18 C17 Sn4 117.4(14) . . ?
C17 C18 C19 109.1(17) . . ?
C20 C19 C18 94.8(17) . . ?
C22 C21 Sn4 104.7(10) . . ?
C23 C22 C21 109.3(11) . . ?
C22 C23 C24 108.3(12) . . ?
C26 C25 Sn4 105.8(13) . . ?
C25 C26 C27 109.4(18) . . ?
C28 C27 C26 110.7(17) . . ?
C30 C29 S2 116.9(10) . . ?
O3 C30 O4 122.9(14) . . ?
O3 C30 C29 121.0(13) . . ?
O4 C30 C29 116.0(13) . . ?
C32 C31 Sn1 114.7(11) . . ?
C31 C32 C33 107.4(13) . . ?
C34 C33 C32 104.4(16) . . ?
C36 C35 Sn1 121.6(11) . . ?
C35 C36 C37 117.3(14) . . ?
C38 C37 C36 117.2(17) . . ?
C40 C39 Sn1 116.0(11) . . ?
C41 C40 C39 117.7(17) . . ?
C40 C41 C42 94.7(18) . . ?
C44 C43 Sn2 109.7(10) . . ?
C45 C44 C43 114.1(12) . . ?
C44 C45 C46 112.1(14) . . ?
C48 C47 Sn2 110.9(10) . . ?
C49 C48 C47 112.2(13) . . ?
C50 C49 C48 109.1(16) . . ?
C52 C51 Sn2 122.2(10) . . ?
C51 C52 C53 118.3(12) . . ?
C54 C53 C52 111.7(12) . . ?
O6 C55 O5 121.8(13) . . ?
O6 C55 C56 119.3(13) . . ?
O5 C55 C56 118.8(13) . . ?
C55 C56 S5 115.6(10) . . ?
N3 C57 S4 113.1(10) . . ?
N3 C57 S5 127.4(11) . . ?
S4 C57 S5 119.5(7) . . ?
N4 C58 S4 113.4(10) . . ?
N4 C58 S6 125.5(11) . . ?
S4 C58 S6 121.0(9) . . ?
C60 C59 S6 113.4(10) . . ?
O8 C60 O7 125.5(15) . . ?
O8 C60 C59 124.4(17) . . ?
O7 C60 C59 110.0(14) . . ?

_refine_diff_density_max         0.864
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.113

####################################################################### 
# 
# 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_160915e
_database_code_depnum_ccdc_archive 'CCDC 1581689'
_audit_update_record             
;
2017-10-24 deposited with the CCDC.
2018-06-04 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         ?
_chemical_formula_sum            'C10 H16 N2 O5 S3 Sn2'
_chemical_formula_weight         577.81

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'
S S 0.1246 0.1234 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.8556(11)
_cell_length_b                   8.8721(8)
_cell_length_c                   16.7333(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.272(3)
_cell_angle_gamma                90
_cell_volume                     1841.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4016
_cell_measurement_theta_min      2.622
_cell_measurement_theta_max      27.974

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.085
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.073
_shelx_estimated_absorpt_T_min   0.366
_shelx_estimated_absorpt_T_max   0.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3656
_exptl_absorpt_correction_T_max  0.6557
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8918
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3239
_reflns_number_gt                2504
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²+6.2950P] 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         3239
_refine_ls_number_parameters     203
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.081
_refine_ls_shift/su_mean         0.002

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
Sn2 Sn 0.62061(4) 0.52508(7) 0.48723(3) 0.0384(2) Uani 1 1 d . U . . .
Sn1 Sn 0.58902(5) 0.27590(7) 0.65902(3) 0.0416(2) Uani 1 1 d . U . . .
S1 S 0.9279(2) 0.2204(3) 0.41587(15) 0.0523(6) Uani 1 1 d . U . . .
S2 S 0.1690(2) 0.0503(3) 0.68488(15) 0.0560(7) Uani 1 1 d . U . . .
S3 S 0.9649(3) 0.3833(4) 0.57946(17) 0.0814(10) Uani 1 1 d . U . . .
O1 O 0.8089(7) 0.2226(12) 0.7388(6) 0.097(3) Uani 1 1 d . U . . .
O2 O 0.7440(6) 0.3547(10) 0.6287(6) 0.083(2) Uani 1 1 d . U . . .
O3 O 0.5387(4) 0.4120(7) 0.5603(3) 0.0402(13) Uani 1 1 d . U . . .
O4 O 0.4050(4) 0.2818(7) 0.6314(4) 0.0479(14) Uani 1 1 d . U . . .
O5 O 0.4120(6) 0.0962(10) 0.7207(5) 0.084(3) Uani 1 1 d . U . . .
N1 N 0.8673(6) 0.1142(9) 0.5388(4) 0.0521(18) Uani 1 1 d . U . . .
N2 N 0.8331(7) 0.0095(9) 0.4748(5) 0.054(2) Uani 1 1 d . U . . .
C1 C 0.8602(6) 0.0495(10) 0.4076(5) 0.0420(18) Uani 1 1 d . U . . .
C2 C 0.9169(7) 0.2274(11) 0.5170(6) 0.049(2) Uani 1 1 d . U . . .
C3 C 0.9323(7) 0.3274(12) 0.6710(6) 0.052(2) Uani 1 1 d . U . . .
H3A H 0.969774 0.233092 0.687956 0.062 Uiso 1 1 calc R U . . .
H3B H 0.964699 0.401160 0.712912 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8173(9) 0.3047(13) 0.6766(8) 0.067(2) Uani 1 1 d . U . . .
C5 C 0.5988(8) 0.3898(15) 0.7710(6) 0.071(3) Uani 1 1 d . U . . .
H5A H 0.652410 0.467616 0.778359 0.107 Uiso 1 1 calc R U . . .
H5B H 0.618416 0.319786 0.816188 0.107 Uiso 1 1 calc R U . . .
H5C H 0.530163 0.433938 0.769419 0.107 Uiso 1 1 calc R U . . .
C6 C 0.5995(8) 0.0547(11) 0.6154(7) 0.063(3) Uani 1 1 d . U . . .
H6A H 0.529227 0.021564 0.584701 0.094 Uiso 1 1 calc R U . . .
H6B H 0.626426 -0.011539 0.661638 0.094 Uiso 1 1 calc R U . . .
H6C H 0.647493 0.053375 0.580177 0.094 Uiso 1 1 calc R U . . .
C7 C 0.7062(9) 0.6966(13) 0.5607(6) 0.066(3) Uani 1 1 d . U . . .
H7A H 0.712927 0.674276 0.617984 0.099 Uiso 1 1 calc R U . . .
H7B H 0.668531 0.790348 0.546494 0.099 Uiso 1 1 calc R U . . .
H7C H 0.776664 0.704491 0.551579 0.099 Uiso 1 1 calc R U . . .
C8 C 0.6446(9) 0.3612(12) 0.4032(6) 0.066(3) Uani 1 1 d . U . . .
H8A H 0.577367 0.340523 0.363356 0.099 Uiso 1 1 calc R U . . .
H8B H 0.671505 0.270440 0.432690 0.099 Uiso 1 1 calc R U . . .
H8C H 0.695835 0.397769 0.375210 0.099 Uiso 1 1 calc R U . . .
C9 C 0.3617(6) 0.1879(11) 0.6734(5) 0.0432(19) Uani 1 1 d . U . . .
C10 C 0.2408(6) 0.2105(11) 0.6586(6) 0.048(2) Uani 1 1 d . U . . .
H10A H 0.210336 0.234458 0.600577 0.058 Uiso 1 1 calc R U . . .
H10B H 0.228794 0.296614 0.690752 0.058 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
Sn2 O3 2.068(5) 3_666 ?
Sn2 O3 2.070(5) . ?
Sn2 C7 2.080(10) . ?
Sn2 C8 2.101(9) . ?
Sn2 O2 2.903(9) . ?
Sn2 Sn2 3.2703(10) 3_666 ?
Sn1 O3 2.011(5) . ?
Sn1 C5 2.103(10) . ?
Sn1 C6 2.110(10) . ?
Sn1 O4 2.289(6) . ?
Sn1 O2 2.292(8) . ?
S1 C1 1.734(9) . ?
S1 C2 1.735(9) . ?
S2 C1 1.736(9) 3_656 ?
S2 C10 1.811(9) . ?
S3 C2 1.746(10) . ?
S3 C3 1.762(9) . ?
O1 C4 1.298(15) . ?
O2 C4 1.153(13) . ?
O4 C9 1.305(10) . ?
O5 C9 1.199(11) . ?
N1 C2 1.293(11) . ?
N1 N2 1.399(11) . ?
N2 C1 1.311(11) . ?
C3 C4 1.519(14) . ?
C9 C10 1.521(11) . ?

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 Sn2 O3 75.6(2) 3_666 . ?
O3 Sn2 C7 110.2(4) 3_666 . ?
O3 Sn2 C7 106.1(3) . . ?
O3 Sn2 C8 103.6(3) 3_666 . ?
O3 Sn2 C8 104.3(4) . . ?
C7 Sn2 C8 138.9(4) . . ?
O3 Sn2 O2 136.6(2) 3_666 . ?
O3 Sn2 O2 61.3(2) . . ?
C7 Sn2 O2 79.0(4) . . ?
C8 Sn2 O2 92.3(3) . . ?
O3 Sn2 Sn2 37.82(14) 3_666 3_666 ?
O3 Sn2 Sn2 37.78(13) . 3_666 ?
C7 Sn2 Sn2 113.2(3) . 3_666 ?
C8 Sn2 Sn2 107.7(3) . 3_666 ?
O2 Sn2 Sn2 98.98(16) . 3_666 ?
O3 Sn1 C5 112.0(4) . . ?
O3 Sn1 C6 108.1(4) . . ?
C5 Sn1 C6 139.5(5) . . ?
O3 Sn1 O4 74.3(2) . . ?
C5 Sn1 O4 89.1(3) . . ?
C6 Sn1 O4 96.2(3) . . ?
O3 Sn1 O2 75.2(3) . . ?
C5 Sn1 O2 101.5(4) . . ?
C6 Sn1 O2 94.0(4) . . ?
O4 Sn1 O2 149.5(3) . . ?
C1 S1 C2 86.7(4) . . ?
C1 S2 C10 100.9(4) 3_656 . ?
C2 S3 C3 99.8(5) . . ?
C4 O2 Sn1 109.1(9) . . ?
C4 O2 Sn2 159.8(9) . . ?
Sn1 O2 Sn2 91.1(2) . . ?
Sn1 O3 Sn2 123.3(2) . 3_666 ?
Sn1 O3 Sn2 132.2(2) . . ?
Sn2 O3 Sn2 104.4(2) 3_666 . ?
C9 O4 Sn1 116.2(5) . . ?
C2 N1 N2 112.2(7) . . ?
C1 N2 N1 112.1(7) . . ?
N2 C1 S1 114.2(7) . . ?
N2 C1 S2 125.6(7) . 3_656 ?
S1 C1 S2 120.2(5) . 3_656 ?
N1 C2 S1 114.9(7) . . ?
N1 C2 S3 124.7(7) . . ?
S1 C2 S3 120.4(5) . . ?
C4 C3 S3 123.3(7) . . ?
O2 C4 O1 123.2(12) . . ?
O2 C4 C3 122.4(12) . . ?
O1 C4 C3 114.4(10) . . ?
O5 C9 O4 123.8(8) . . ?
O5 C9 C10 123.2(8) . . ?
O4 C9 C10 113.0(8) . . ?
C9 C10 S2 114.9(7) . . ?

_refine_diff_density_max         2.048
_refine_diff_density_min         -1.174
_refine_diff_density_rms         0.166

