# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

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

data_480r
_database_code_depnum_ccdc_archive 'CCDC 1860608'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultatea de Chimie si Inginerie Chimica,  Universitatea Babes-Bolyai
Romania
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Cl O2 Sn'
_chemical_formula_sum            'C11 H15 Cl O2 Sn'
_chemical_formula_weight         333.37

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   9.471(3)
_cell_length_b                   9.488(3)
_cell_length_c                   15.221(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.228(6)
_cell_angle_gamma                90
_cell_volume                     1313.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2941
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      23.66
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    2.128
_shelx_estimated_absorpt_T_min   0.577
_shelx_estimated_absorpt_T_max   0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_T_max  0.620
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(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_reflns_number            9229
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2319
_reflns_number_gt                1860
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0455P)²+2.2906P] 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         2319
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1068
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3948(6) 0.2275(5) 0.3666(3) 0.0485(11) Uani 1 1 d . . . . .
C2 C 0.3067(5) 0.3426(5) 0.3722(3) 0.0510(11) Uani 1 1 d . . . . .
C3 C 0.1937(6) 0.3285(8) 0.4133(4) 0.0747(17) Uani 1 1 d . . . . .
H3 H 0.1330 0.4047 0.4153 0.090 Uiso 1 1 calc R U . . .
C4 C 0.1719(7) 0.2026(11) 0.4506(4) 0.088(2) Uani 1 1 d . . . . .
H4 H 0.0979 0.1941 0.4796 0.106 Uiso 1 1 calc R U . . .
C5 C 0.2571(7) 0.0896(8) 0.4459(4) 0.0774(18) Uani 1 1 d . . . . .
H5 H 0.2404 0.0039 0.4711 0.093 Uiso 1 1 calc R U . . .
C6 C 0.3683(6) 0.1009(6) 0.4042(3) 0.0594(13) Uani 1 1 d . . . . .
H6 H 0.4260 0.0228 0.4012 0.071 Uiso 1 1 calc R U . . .
C7 C 0.3294(6) 0.4839(6) 0.3348(4) 0.0652(14) Uani 1 1 d . . . . .
H7 H 0.2441 0.5076 0.2835 0.078 Uiso 1 1 calc R U . . .
C10 C 0.5127(11) 0.6263(7) 0.3193(7) 0.120(3) Uani 1 1 d . . . . .
H10A H 0.4970 0.6750 0.2613 0.144 Uiso 1 1 calc R U . . .
H10B H 0.6171 0.6256 0.3504 0.144 Uiso 1 1 calc R U . . .
C11 C 0.4309(11) 0.6937(8) 0.3754(5) 0.106(3) Uani 1 1 d . . . . .
H11A H 0.4975 0.7369 0.4288 0.127 Uiso 1 1 calc R U . . .
H11B H 0.3662 0.7658 0.3408 0.127 Uiso 1 1 calc R U . . .
C8 C 0.5193(8) 0.2805(7) 0.1633(4) 0.0773(17) Uani 1 1 d . . . . .
H8A H 0.5985 0.2456 0.1415 0.116 Uiso 1 1 calc R U . . .
H8B H 0.5058 0.3792 0.1498 0.116 Uiso 1 1 calc R U . . .
H8C H 0.4306 0.2306 0.1336 0.116 Uiso 1 1 calc R U . . .
C9 C 0.7679(7) 0.3259(10) 0.3942(5) 0.101(2) Uani 1 1 d . . . . .
H9A H 0.8273 0.3663 0.3589 0.151 Uiso 1 1 calc R U . . .
H9B H 0.8201 0.2495 0.4304 0.151 Uiso 1 1 calc R U . . .
H9C H 0.7463 0.3965 0.4338 0.151 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6335(2) -0.00092(19) 0.30421(13) 0.1022(7) Uani 1 1 d . . . . .
O1 O 0.4563(5) 0.4861(4) 0.3055(3) 0.0815(12) Uani 1 1 d . . . . .
O2 O 0.3507(6) 0.5884(5) 0.4010(3) 0.1030(16) Uani 1 1 d . . . . .
Sn1 Sn 0.56977(4) 0.24996(4) 0.30540(2) 0.05734(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.382(7) . ?
C1 C2 1.391(7) . ?
C1 Sn1 2.127(5) . ?
C2 C3 1.389(8) . ?
C2 C7 1.496(7) . ?
C3 C4 1.363(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.387(6) . ?
C7 O1 1.393(7) . ?
C7 H7 0.9800 . ?
C10 O1 1.427(7) . ?
C10 C11 1.452(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.375(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C8 Sn1 2.101(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 Sn1 2.109(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
Cl1 Sn1 2.4571(18) . ?
O1 Sn1 2.486(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
C6 C1 C2 118.4(5) . . ?
C6 C1 Sn1 121.5(4) . . ?
C2 C1 Sn1 120.1(4) . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 C7 118.0(5) . . ?
C1 C2 C7 121.9(5) . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.3(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.6(6) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O2 C7 O1 105.0(5) . . ?
O2 C7 C2 111.8(5) . . ?
O1 C7 C2 111.3(4) . . ?
O2 C7 H7 109.6 . . ?
O1 C7 H7 109.6 . . ?
C2 C7 H7 109.6 . . ?
O1 C10 C11 104.9(7) . . ?
O1 C10 H10A 110.8 . . ?
C11 C10 H10A 110.8 . . ?
O1 C10 H10B 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
O2 C11 C10 105.9(6) . . ?
O2 C11 H11A 110.6 . . ?
C10 C11 H11A 110.6 . . ?
O2 C11 H11B 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
Sn1 C8 H8A 109.5 . . ?
Sn1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Sn1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Sn1 C9 H9A 109.5 . . ?
Sn1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Sn1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 O1 C10 106.7(5) . . ?
C7 O1 Sn1 113.5(3) . . ?
C10 O1 Sn1 134.1(5) . . ?
C11 O2 C7 107.0(5) . . ?
C8 Sn1 C9 121.2(3) . . ?
C8 Sn1 C1 119.0(2) . . ?
C9 Sn1 C1 114.6(2) . . ?
C8 Sn1 Cl1 96.42(18) . . ?
C9 Sn1 Cl1 99.2(3) . . ?
C1 Sn1 Cl1 97.41(13) . . ?
C8 Sn1 O1 84.4(2) . . ?
C9 Sn1 O1 89.9(3) . . ?
C1 Sn1 O1 72.54(15) . . ?
Cl1 Sn1 O1 168.69(11) . . ?

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
C6 C1 C2 C3 -1.1(7) . . . . ?
Sn1 C1 C2 C3 -179.1(4) . . . . ?
C6 C1 C2 C7 179.0(4) . . . . ?
Sn1 C1 C2 C7 0.9(6) . . . . ?
C1 C2 C3 C4 2.0(9) . . . . ?
C7 C2 C3 C4 -178.1(6) . . . . ?
C2 C3 C4 C5 -1.8(10) . . . . ?
C3 C4 C5 C6 0.7(10) . . . . ?
C4 C5 C6 C1 0.1(9) . . . . ?
C2 C1 C6 C5 0.0(8) . . . . ?
Sn1 C1 C6 C5 178.1(4) . . . . ?
C3 C2 C7 O2 56.1(7) . . . . ?
C1 C2 C7 O2 -124.0(5) . . . . ?
C3 C2 C7 O1 173.1(5) . . . . ?
C1 C2 C7 O1 -7.0(7) . . . . ?
O1 C10 C11 O2 8.1(10) . . . . ?
O2 C7 O1 C10 -27.7(7) . . . . ?
C2 C7 O1 C10 -148.8(6) . . . . ?
O2 C7 O1 Sn1 129.8(4) . . . . ?
C2 C7 O1 Sn1 8.6(5) . . . . ?
C11 C10 O1 C7 12.1(8) . . . . ?
C11 C10 O1 Sn1 -138.6(6) . . . . ?
C10 C11 O2 C7 -25.6(9) . . . . ?
O1 C7 O2 C11 33.4(7) . . . . ?
C2 C7 O2 C11 154.3(6) . . . . ?

_refine_diff_density_max         0.903
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_703r
_database_code_depnum_ccdc_archive 'CCDC 1860610'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultatea de Chimie si Inginerie Chimica,  Universitatea Babes-Bolyai
Romania
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 Cl2 N2 Sn2'
_chemical_formula_sum            'C20 H26 Cl2 N2 Sn2'
_chemical_formula_weight         602.71

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'
Cl Cl 0.1484 0.1585 '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                   10.681(2)
_cell_length_b                   9.7590(19)
_cell_length_c                   11.374(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.171(3)
_cell_angle_gamma                90
_cell_volume                     1138.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3534
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      24.12
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.435
_shelx_estimated_absorpt_T_min   0.712
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10741
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.539
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.539
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.539
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2007
_reflns_number_gt                1913
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0765P)²+6.5254P] 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         2007
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1567
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.181
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0176(7) 0.3939(7) 0.7801(7) 0.0316(15) Uani 1 1 d . . . . .
C2 C -0.0837(7) 0.3888(7) 0.8693(7) 0.0329(15) Uani 1 1 d . . . . .
C3 C -0.1682(8) 0.4923(9) 0.8799(8) 0.047(2) Uani 1 1 d . . . . .
H3 H -0.2121 0.4865 0.9398 0.056 Uiso 1 1 calc R U . . .
C4 C -0.1878(9) 0.6026(10) 0.8036(9) 0.054(2) Uani 1 1 d . . . . .
H4 H -0.2440 0.6723 0.8121 0.065 Uiso 1 1 calc R U . . .
C5 C -0.1241(9) 0.6107(10) 0.7137(8) 0.053(2) Uani 1 1 d . . . . .
H5 H -0.1384 0.6850 0.6605 0.063 Uiso 1 1 calc R U . . .
C6 C -0.0388(9) 0.5075(9) 0.7032(7) 0.0440(19) Uani 1 1 d . . . . .
H6 H 0.0053 0.5143 0.6435 0.053 Uiso 1 1 calc R U . . .
C7 C -0.0579(8) 0.2730(8) 0.9545(7) 0.0375(18) Uani 1 1 d . . . . .
H7 H -0.0947 0.2714 1.0196 0.045 Uiso 1 1 calc R U . . .
C8 C 0.2942(8) 0.2288(8) 0.9225(10) 0.048(2) Uani 1 1 d . . . . .
H8A H 0.3663 0.2282 0.8875 0.073 Uiso 1 1 calc R U . . .
H8B H 0.2979 0.1487 0.9722 0.073 Uiso 1 1 calc R U . . .
H8C H 0.2988 0.3093 0.9720 0.073 Uiso 1 1 calc R U . . .
C9 C 0.0412(10) 0.0506(10) 0.6782(8) 0.056(2) Uani 1 1 d . . . . .
H9A H -0.0155 0.0036 0.7170 0.083 Uiso 1 1 calc R U . . .
H9B H 0.1124 -0.0084 0.6759 0.083 Uiso 1 1 calc R U . . .
H9C H -0.0065 0.0751 0.5962 0.083 Uiso 1 1 calc R U . . .
C10 C 0.0385(9) 0.0621(9) 1.0279(8) 0.051(2) Uani 1 1 d . . . . .
H10A H 0.0139 0.0895 1.1004 0.061 Uiso 1 1 calc R U . . .
H10B H 0.1307 0.0401 1.0523 0.061 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1999(3) 0.3278(3) 0.6129(2) 0.0633(7) Uani 1 1 d . . . . .
N1 N 0.0142(7) 0.1746(7) 0.9400(6) 0.0374(14) Uani 1 1 d . . . . .
Sn1 Sn 0.11437(5) 0.22950(5) 0.77824(5) 0.0349(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.390(10) . ?
C1 C6 1.390(10) . ?
C1 Sn1 2.139(7) . ?
C2 C3 1.382(11) . ?
C2 C7 1.464(11) . ?
C3 C4 1.362(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(12) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.270(11) . ?
C7 H7 0.9300 . ?
C8 Sn1 2.151(9) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 Sn1 2.112(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.458(10) . ?
C10 C10 1.502(17) 3_557 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
Cl1 Sn1 2.499(2) . ?
N1 Sn1 2.432(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.4(7) . . ?
C2 C1 Sn1 116.8(5) . . ?
C6 C1 Sn1 125.7(5) . . ?
C3 C2 C1 121.0(7) . . ?
C3 C2 C7 120.9(7) . . ?
C1 C2 C7 118.1(7) . . ?
C4 C3 C2 120.7(8) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.9(8) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.6(8) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.4(8) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
N1 C7 C2 120.5(7) . . ?
N1 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
Sn1 C8 H8A 109.5 . . ?
Sn1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Sn1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Sn1 C9 H9A 109.5 . . ?
Sn1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Sn1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C10 110.3(9) . 3_557 ?
N1 C10 H10A 109.6 . . ?
C10 C10 H10A 109.6 3_557 . ?
N1 C10 H10B 109.6 . . ?
C10 C10 H10B 109.6 3_557 . ?
H10A C10 H10B 108.1 . . ?
C7 N1 C10 118.6(7) . . ?
C7 N1 Sn1 110.0(5) . . ?
C10 N1 Sn1 130.7(6) . . ?
C9 Sn1 C1 118.7(3) . . ?
C9 Sn1 C8 121.7(4) . . ?
C1 Sn1 C8 116.5(3) . . ?
C9 Sn1 N1 92.9(3) . . ?
C1 Sn1 N1 74.2(2) . . ?
C8 Sn1 N1 84.8(3) . . ?
C9 Sn1 Cl1 94.0(3) . . ?
C1 Sn1 Cl1 95.7(2) . . ?
C8 Sn1 Cl1 98.0(3) . . ?
N1 Sn1 Cl1 169.67(17) . . ?

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
C6 C1 C2 C3 0.7(12) . . . . ?
Sn1 C1 C2 C3 178.2(6) . . . . ?
C6 C1 C2 C7 -177.3(7) . . . . ?
Sn1 C1 C2 C7 0.2(9) . . . . ?
C1 C2 C3 C4 -0.6(13) . . . . ?
C7 C2 C3 C4 177.3(8) . . . . ?
C2 C3 C4 C5 0.8(14) . . . . ?
C3 C4 C5 C6 -1.1(14) . . . . ?
C4 C5 C6 C1 1.3(14) . . . . ?
C2 C1 C6 C5 -1.0(12) . . . . ?
Sn1 C1 C6 C5 -178.3(6) . . . . ?
C3 C2 C7 N1 176.1(8) . . . . ?
C1 C2 C7 N1 -5.9(11) . . . . ?
C2 C7 N1 C10 179.3(7) . . . . ?
C2 C7 N1 Sn1 7.5(9) . . . . ?
C10 C10 N1 C7 105.3(11) 3_557 . . . ?
C10 C10 N1 Sn1 -84.9(11) 3_557 . . . ?

_refine_diff_density_max         3.236
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.230

####################################################################### 
# 
# 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_658r
_database_code_depnum_ccdc_archive 'CCDC 1860615'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultatea de Chimie si Inginerie Chimica,  Universitatea Babes-Bolyai
Romania
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 Cl O Sn'
_chemical_formula_weight         289.34

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   12.485(2)
_cell_length_b                   15.563(3)
_cell_length_c                   23.473(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4560.7(13)
_cell_formula_units_Z            16
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    8808
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      22.91
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_F_000             2240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    2.432
_shelx_estimated_absorpt_T_min   0.529
_shelx_estimated_absorpt_T_max   0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5291
_exptl_absorpt_correction_T_max  0.6047
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41303
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.735
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4025
_reflns_number_gt                3696
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0289P)²+9.3299P] 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         4025
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_restrained_S_all      1.284
_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
Cl2 Cl 0.37379(17) 0.47317(14) 0.80311(10) 0.0986(7) Uani 1 1 d . . . . .
C1 C 0.4438(4) 0.1424(3) 0.4973(2) 0.0482(13) Uani 1 1 d . . . . .
C2 C 0.3722(5) 0.1297(4) 0.4523(3) 0.0573(15) Uani 1 1 d . . . . .
C3 C 0.2973(5) 0.0638(5) 0.4548(4) 0.079(2) Uani 1 1 d . . . . .
H3 H 0.2491 0.0560 0.4250 0.095 Uiso 1 1 calc R U . . .
C4 C 0.2946(7) 0.0104(5) 0.5011(4) 0.091(3) Uani 1 1 d . . . . .
H4 H 0.2455 -0.0344 0.5023 0.109 Uiso 1 1 calc R U . . .
C5 C 0.3634(6) 0.0225(4) 0.5454(4) 0.080(2) Uani 1 1 d . . . . .
H5 H 0.3594 -0.0129 0.5773 0.096 Uiso 1 1 calc R U . . .
C6 C 0.4391(5) 0.0871(4) 0.5432(3) 0.0614(16) Uani 1 1 d . . . . .
H6 H 0.4875 0.0933 0.5730 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3792(6) 0.1873(5) 0.4035(3) 0.0680(18) Uani 1 1 d . . . . .
H7 H 0.3336 0.1782 0.3728 0.082 Uiso 1 1 calc R U . . .
C8 C 0.4865(7) 0.3729(5) 0.5033(3) 0.091(2) Uani 1 1 d . . . . .
H8A H 0.5417 0.4100 0.5176 0.136 Uiso 1 1 calc R U . . .
H8B H 0.4294 0.3694 0.5306 0.136 Uiso 1 1 calc R U . . .
H8C H 0.4593 0.3956 0.4681 0.136 Uiso 1 1 calc R U . . .
C9 C 0.6845(5) 0.2392(5) 0.4352(3) 0.087(2) Uani 1 1 d . . . . .
H9A H 0.7125 0.2956 0.4278 0.131 Uiso 1 1 calc R U . . .
H9B H 0.6637 0.2127 0.4000 0.131 Uiso 1 1 calc R U . . .
H9C H 0.7385 0.2049 0.4534 0.131 Uiso 1 1 calc R U . . .
C10 C 0.5690(5) 0.6032(3) 0.7467(2) 0.0507(13) Uani 1 1 d . . . . .
C11 C 0.6512(5) 0.6321(4) 0.7113(2) 0.0548(14) Uani 1 1 d . . . . .
C12 C 0.7189(6) 0.6983(4) 0.7281(3) 0.0710(18) Uani 1 1 d . . . . .
H12 H 0.7741 0.7166 0.7044 0.085 Uiso 1 1 calc R U . . .
C13 C 0.7032(7) 0.7365(5) 0.7805(3) 0.084(2) Uani 1 1 d . . . . .
H13 H 0.7477 0.7811 0.7922 0.101 Uiso 1 1 calc R U . . .
C14 C 0.6222(6) 0.7089(5) 0.8153(3) 0.078(2) Uani 1 1 d . . . . .
H14 H 0.6122 0.7348 0.8506 0.094 Uiso 1 1 calc R U . . .
C15 C 0.5555(5) 0.6433(4) 0.7986(3) 0.0637(16) Uani 1 1 d . . . . .
H15 H 0.5005 0.6256 0.8226 0.076 Uiso 1 1 calc R U . . .
C16 C 0.6643(5) 0.5914(4) 0.6562(3) 0.0671(17) Uani 1 1 d . . . . .
H16 H 0.7195 0.6103 0.6327 0.080 Uiso 1 1 calc R U . . .
C17 C 0.3571(6) 0.5081(6) 0.6582(4) 0.105(3) Uani 1 1 d . . . . .
H17A H 0.3846 0.5010 0.6204 0.157 Uiso 1 1 calc R U . . .
H17B H 0.3268 0.5645 0.6620 0.157 Uiso 1 1 calc R U . . .
H17C H 0.3028 0.4658 0.6653 0.157 Uiso 1 1 calc R U . . .
C18 C 0.5722(6) 0.3780(5) 0.7205(4) 0.101(3) Uani 1 1 d . . . . .
H18A H 0.5397 0.3389 0.7470 0.152 Uiso 1 1 calc R U . . .
H18B H 0.6440 0.3906 0.7325 0.152 Uiso 1 1 calc R U . . .
H18C H 0.5737 0.3524 0.6833 0.152 Uiso 1 1 calc R U . . .
Cl1 Cl 0.63780(15) 0.23001(12) 0.58130(8) 0.0847(6) Uani 1 1 d . . . . .
O1 O 0.4415(4) 0.2463(3) 0.4014(2) 0.0775(13) Uani 1 1 d . . . . .
O2 O 0.6069(4) 0.5338(3) 0.63921(18) 0.0719(12) Uani 1 1 d . . . . .
Sn1 Sn 0.55013(3) 0.24917(3) 0.48910(2) 0.05261(14) Uani 1 1 d . . . . .
Sn2 Sn 0.48231(3) 0.49298(3) 0.71757(2) 0.05879(15) 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
Cl2 Sn2 2.4418(19) . ?
C1 C6 1.380(8) . ?
C1 C2 1.398(8) . ?
C1 Sn1 2.135(5) . ?
C2 C3 1.389(9) . ?
C2 C7 1.457(9) . ?
C3 C4 1.368(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.205(8) . ?
C7 H7 0.9300 . ?
C8 Sn1 2.110(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 Sn1 2.106(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.380(8) . ?
C10 C11 1.394(8) . ?
C10 Sn2 2.141(6) . ?
C11 C12 1.391(8) . ?
C11 C16 1.448(8) . ?
C12 C13 1.379(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.215(7) . ?
C16 H16 0.9300 . ?
C17 Sn2 2.107(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 Sn2 2.113(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
Cl1 Sn1 2.4434(17) . ?
O1 Sn1 2.466(5) . ?
O2 Sn2 2.491(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
C6 C1 C2 118.3(5) . . ?
C6 C1 Sn1 125.7(4) . . ?
C2 C1 Sn1 116.0(4) . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 C7 121.8(6) . . ?
C1 C2 C7 117.9(6) . . ?
C4 C3 C2 119.8(7) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.5(7) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.1(7) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.9(7) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C2 122.7(6) . . ?
O1 C7 H7 118.6 . . ?
C2 C7 H7 118.6 . . ?
Sn1 C8 H8A 109.5 . . ?
Sn1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Sn1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Sn1 C9 H9A 109.5 . . ?
Sn1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Sn1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 118.1(6) . . ?
C15 C10 Sn2 125.6(4) . . ?
C11 C10 Sn2 116.1(4) . . ?
C12 C11 C10 121.1(6) . . ?
C12 C11 C16 120.6(6) . . ?
C10 C11 C16 118.3(5) . . ?
C13 C12 C11 119.1(6) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.1(7) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.7(6) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.9(6) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O2 C16 C11 123.3(6) . . ?
O2 C16 H16 118.4 . . ?
C11 C16 H16 118.4 . . ?
Sn2 C17 H17A 109.5 . . ?
Sn2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Sn2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Sn2 C18 H18A 109.5 . . ?
Sn2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Sn2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 O1 Sn1 109.5(4) . . ?
C16 O2 Sn2 108.3(4) . . ?
C9 Sn1 C8 117.5(3) . . ?
C9 Sn1 C1 119.5(3) . . ?
C8 Sn1 C1 117.5(3) . . ?
C9 Sn1 Cl1 99.5(2) . . ?
C8 Sn1 Cl1 98.1(2) . . ?
C1 Sn1 Cl1 95.94(16) . . ?
C9 Sn1 O1 86.3(3) . . ?
C8 Sn1 O1 86.6(2) . . ?
C1 Sn1 O1 73.73(19) . . ?
Cl1 Sn1 O1 169.65(13) . . ?
C17 Sn2 C18 120.7(3) . . ?
C17 Sn2 C10 119.8(3) . . ?
C18 Sn2 C10 113.5(3) . . ?
C17 Sn2 Cl2 98.4(3) . . ?
C18 Sn2 Cl2 99.3(3) . . ?
C10 Sn2 Cl2 96.86(16) . . ?
C17 Sn2 O2 87.0(3) . . ?
C18 Sn2 O2 84.7(3) . . ?
C10 Sn2 O2 73.47(18) . . ?
Cl2 Sn2 O2 170.33(12) . . ?

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
C6 C1 C2 C3 1.2(8) . . . . ?
Sn1 C1 C2 C3 -177.6(4) . . . . ?
C6 C1 C2 C7 -178.8(5) . . . . ?
Sn1 C1 C2 C7 2.4(7) . . . . ?
C1 C2 C3 C4 -0.9(10) . . . . ?
C7 C2 C3 C4 179.1(6) . . . . ?
C2 C3 C4 C5 1.4(11) . . . . ?
C3 C4 C5 C6 -2.2(11) . . . . ?
C2 C1 C6 C5 -2.0(9) . . . . ?
Sn1 C1 C6 C5 176.7(5) . . . . ?
C4 C5 C6 C1 2.6(10) . . . . ?
C3 C2 C7 O1 177.8(6) . . . . ?
C1 C2 C7 O1 -2.2(9) . . . . ?
C15 C10 C11 C12 1.2(9) . . . . ?
Sn2 C10 C11 C12 -174.3(5) . . . . ?
C15 C10 C11 C16 -178.8(5) . . . . ?
Sn2 C10 C11 C16 5.8(7) . . . . ?
C10 C11 C12 C13 -0.9(10) . . . . ?
C16 C11 C12 C13 179.1(6) . . . . ?
C11 C12 C13 C14 0.4(11) . . . . ?
C12 C13 C14 C15 -0.2(12) . . . . ?
C13 C14 C15 C10 0.5(11) . . . . ?
C11 C10 C15 C14 -1.0(9) . . . . ?
Sn2 C10 C15 C14 173.9(5) . . . . ?
C12 C11 C16 O2 -179.4(6) . . . . ?
C10 C11 C16 O2 0.5(9) . . . . ?
C2 C7 O1 Sn1 0.9(7) . . . . ?
C11 C16 O2 Sn2 -5.4(8) . . . . ?

_refine_diff_density_max         0.563
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_741r_sq
_database_code_depnum_ccdc_archive 'CCDC 1860612'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultatea de Chimie si Inginerie Chimica,  Universitatea Babes-Bolyai
Romania
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 N4 S2 Sn2'
_chemical_formula_sum            'C22 H26 N4 S2 Sn2'
_chemical_formula_weight         647.97

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'
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                   12.5737(18)
_cell_length_b                   18.303(3)
_cell_length_c                   12.8154(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.033(3)
_cell_angle_gamma                90
_cell_volume                     2947.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3014
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      20.59
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    1.850
_shelx_estimated_absorpt_T_min   0.598
_shelx_estimated_absorpt_T_max   0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5291
_exptl_absorpt_correction_T_max  0.6047
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13802
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.006
_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             2595
_reflns_number_gt                2216
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0406P)²+2.1253P] 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         2595
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5934(3) 0.7244(2) 0.8955(3) 0.0520(10) Uani 1 1 d . . . . .
C2 C 0.5473(4) 0.7928(2) 0.8876(4) 0.0649(12) Uani 1 1 d . . . . .
C3 C 0.6061(5) 0.8534(3) 0.8589(5) 0.0892(17) Uani 1 1 d . . . . .
H3 H 0.5742 0.8992 0.8544 0.107 Uiso 1 1 calc R U . . .
C4 C 0.7112(5) 0.8451(3) 0.8373(4) 0.0883(17) Uani 1 1 d . . . . .
H4 H 0.7511 0.8855 0.8186 0.106 Uiso 1 1 calc R U . . .
C5 C 0.7574(4) 0.7781(3) 0.8431(4) 0.0729(14) Uani 1 1 d . . . . .
H5 H 0.8286 0.7729 0.8271 0.087 Uiso 1 1 calc R U . . .
C6 C 0.6998(3) 0.7176(3) 0.8725(3) 0.0609(12) Uani 1 1 d . . . . .
H6 H 0.7327 0.6722 0.8768 0.073 Uiso 1 1 calc R U . . .
C7 C 0.4336(4) 0.7999(3) 0.9055(4) 0.0782(15) Uani 1 1 d . . . . .
H7 H 0.4004 0.8450 0.8961 0.094 Uiso 1 1 calc R U . . .
C10 C 0.2636(4) 0.7539(4) 0.9450(4) 0.0900(17) Uani 1 1 d . . . . .
H10A H 0.2417 0.8017 0.9196 0.108 Uiso 1 1 calc R U . . .
H10B H 0.2259 0.7173 0.9033 0.108 Uiso 1 1 calc R U . . .
C9 C 0.3870(4) 0.5818(3) 0.8441(4) 0.0754(14) Uani 1 1 d . . . . .
H9A H 0.3220 0.5712 0.8782 0.113 Uiso 1 1 calc R U . . .
H9B H 0.4199 0.5370 0.8235 0.113 Uiso 1 1 calc R U . . .
H9C H 0.3717 0.6113 0.7834 0.113 Uiso 1 1 calc R U . . .
C8 C 0.4725(4) 0.6302(2) 1.1098(3) 0.0650(12) Uani 1 1 d . . . . .
H8A H 0.5230 0.5957 1.1385 0.098 Uiso 1 1 calc R U . . .
H8B H 0.4016 0.6137 1.1227 0.098 Uiso 1 1 calc R U . . .
H8C H 0.4841 0.6770 1.1420 0.098 Uiso 1 1 calc R U . . .
C11 C 0.6986(5) 0.5283(3) 0.9388(4) 0.0753(14) Uani 1 1 d . . . . .
N1 N 0.3794(3) 0.7451(2) 0.9338(3) 0.0697(11) Uani 1 1 d . . . . .
N2 N 0.6215(3) 0.5568(2) 0.9451(3) 0.0722(11) Uani 1 1 d . . . . .
S1 S 0.80992(16) 0.48476(10) 0.9318(2) 0.1590(10) Uani 1 1 d . . . . .
Sn1 Sn 0.49139(2) 0.63922(2) 0.94801(2) 0.05405(14) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(6) . ?
C1 C6 1.386(6) . ?
C1 Sn1 2.143(4) . ?
C2 C3 1.390(6) . ?
C2 C7 1.462(7) . ?
C3 C4 1.369(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.273(6) . ?
C7 H7 0.9300 . ?
C10 C10 1.470(10) 7_567 ?
C10 N1 1.477(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 Sn1 2.115(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 Sn1 2.101(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C11 N2 1.106(6) . ?
C11 S1 1.616(6) . ?
N1 Sn1 2.398(4) . ?
N2 Sn1 2.227(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
C2 C1 C6 118.1(4) . . ?
C2 C1 Sn1 115.3(3) . . ?
C6 C1 Sn1 126.5(3) . . ?
C1 C2 C3 121.1(4) . . ?
C1 C2 C7 118.7(4) . . ?
C3 C2 C7 120.2(5) . . ?
C4 C3 C2 119.5(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C2 120.7(4) . . ?
N1 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C10 C10 N1 110.3(6) 7_567 . ?
C10 C10 H10A 109.6 7_567 . ?
N1 C10 H10A 109.6 . . ?
C10 C10 H10B 109.6 7_567 . ?
N1 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
Sn1 C9 H9A 109.5 . . ?
Sn1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Sn1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Sn1 C8 H8A 109.5 . . ?
Sn1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Sn1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C11 S1 178.3(5) . . ?
C7 N1 C10 118.7(4) . . ?
C7 N1 Sn1 109.9(3) . . ?
C10 N1 Sn1 131.3(4) . . ?
C11 N2 Sn1 165.2(4) . . ?
C8 Sn1 C9 119.49(19) . . ?
C8 Sn1 C1 117.18(16) . . ?
C9 Sn1 C1 121.94(17) . . ?
C8 Sn1 N2 94.12(17) . . ?
C9 Sn1 N2 95.33(18) . . ?
C1 Sn1 N2 92.28(16) . . ?
C8 Sn1 N1 92.96(16) . . ?
C9 Sn1 N1 90.22(17) . . ?
C1 Sn1 N1 75.21(15) . . ?
N2 Sn1 N1 167.41(15) . . ?

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
C6 C1 C2 C3 -1.0(7) . . . . ?
Sn1 C1 C2 C3 177.2(4) . . . . ?
C6 C1 C2 C7 176.3(4) . . . . ?
Sn1 C1 C2 C7 -5.6(6) . . . . ?
C1 C2 C3 C4 0.5(9) . . . . ?
C7 C2 C3 C4 -176.7(5) . . . . ?
C2 C3 C4 C5 0.5(9) . . . . ?
C3 C4 C5 C6 -1.1(9) . . . . ?
C4 C5 C6 C1 0.6(7) . . . . ?
C2 C1 C6 C5 0.4(7) . . . . ?
Sn1 C1 C6 C5 -177.5(3) . . . . ?
C1 C2 C7 N1 4.1(7) . . . . ?
C3 C2 C7 N1 -178.6(5) . . . . ?
C2 C7 N1 C10 -176.5(4) . . . . ?
C2 C7 N1 Sn1 -0.6(6) . . . . ?
C10 C10 N1 C7 -113.6(7) 7_567 . . . ?
C10 C10 N1 Sn1 71.6(8) 7_567 . . . ?

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_745r1
_database_code_depnum_ccdc_archive 'CCDC 1860614'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultatea de Chimie si Inginerie Chimica,  Universitatea Babes-Bolyai
Romania
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N O S Sn'
_chemical_formula_sum            'C10 H11 N O S Sn'
_chemical_formula_weight         311.95

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           12
_space_group_name_H-M_alt        'I 2/m'
_space_group_name_Hall           '-I 2y'

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

_cell_length_a                   13.670(3)
_cell_length_b                   7.4330(15)
_cell_length_c                   24.401(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.77(3)
_cell_angle_gamma                90
_cell_volume                     2456.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3961
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      23.62
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    2.220
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5279
_exptl_absorpt_correction_T_max  0.5556
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '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_reflns_number            11627
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.621
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2334
_reflns_number_gt                2060
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0361P)²+3.0379P] 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         2334
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1314(4) 0.0000 0.3824(2) 0.0572(13) Uani 1 2 d S T P . .
C2 C 0.2332(4) 0.0000 0.3917(2) 0.0606(14) Uani 1 2 d S T P . .
C3 C 0.2838(5) 0.0000 0.4451(3) 0.0794(18) Uani 1 2 d S T P . .
H3 H 0.3525 0.0000 0.4507 0.095 Uiso 1 2 calc R U P . .
C4 C 0.2322(6) 0.0000 0.4894(3) 0.093(2) Uani 1 2 d S T P . .
H4 H 0.2652 0.0000 0.5253 0.111 Uiso 1 2 calc R U P . .
C5 C 0.1303(6) 0.0000 0.4799(3) 0.113(3) Uani 1 2 d S T P . .
H5 H 0.0948 0.0000 0.5098 0.135 Uiso 1 2 calc R U P . .
C6 C 0.0802(5) 0.0000 0.4269(3) 0.088(2) Uani 1 2 d S T P . .
H6 H 0.0115 0.0000 0.4215 0.105 Uiso 1 2 calc R U P . .
C7 C 0.2860(5) 0.0000 0.3435(3) 0.0780(18) Uani 1 2 d S T P . .
H7 H 0.3547 0.0000 0.3496 0.094 Uiso 1 2 calc R U P . .
C8 C 0.0618(3) 0.2439(6) 0.25289(19) 0.0779(12) Uani 1 1 d . . . . .
H8A H 0.0950 0.2287 0.2209 0.117 Uiso 1 1 calc R U . . .
H8B H 0.0943 0.3361 0.2762 0.117 Uiso 1 1 calc R U . . .
H8C H -0.0056 0.2778 0.2414 0.117 Uiso 1 1 calc R U . . .
C9 C -0.1647(5) 0.0000 0.3257(2) 0.0632(14) Uani 1 2 d S T P . .
C11 C 0.7266(4) 0.0000 0.0874(2) 0.0679(16) Uani 1 2 d S T P . .
C12 C 0.7139(4) 0.0000 0.1421(2) 0.0644(15) Uani 1 2 d S T P . .
C13 C 0.6218(5) 0.0000 0.1601(3) 0.085(2) Uani 1 2 d S T P . .
H13 H 0.6168 0.0000 0.1977 0.102 Uiso 1 2 calc R U P . .
C14 C 0.5399(6) 0.0000 0.1229(4) 0.119(3) Uani 1 2 d S T P . .
H14 H 0.4775 0.0000 0.1341 0.143 Uiso 1 2 calc R U P . .
C15 C 0.5504(6) 0.0000 0.0691(4) 0.187(7) Uani 1 2 d S T P . .
H15 H 0.4939 0.0000 0.0432 0.225 Uiso 1 2 calc R U P . .
C16 C 0.6428(6) 0.0000 0.0500(3) 0.152(5) Uani 1 2 d S T P . .
H16 H 0.6469 0.0000 0.0122 0.183 Uiso 1 2 calc R U P . .
C17 C 0.8014(6) 0.0000 0.1817(3) 0.098(2) Uani 1 2 d S T P . .
H17 H 0.7938 0.0000 0.2190 0.118 Uiso 1 2 calc R U P . .
C18 C 0.9545(3) 0.2426(6) 0.07668(19) 0.0751(12) Uani 1 1 d . . . . .
H18A H 1.0137 0.2266 0.1022 0.113 Uiso 1 1 calc R U . . .
H18B H 0.9150 0.3355 0.0900 0.113 Uiso 1 1 calc R U . . .
H18C H 0.9715 0.2763 0.0412 0.113 Uiso 1 1 calc R U . . .
C19 C 0.8085(5) 0.0000 -0.0668(3) 0.0687(16) Uani 1 2 d S T P . .
N1 N -0.0834(4) 0.0000 0.3176(2) 0.0760(15) Uani 1 2 d S T P . .
N2 N 0.8355(5) 0.0000 -0.0196(2) 0.0923(18) Uani 1 2 d S T P . .
O1 O 0.2463(3) 0.0000 0.29689(19) 0.0763(12) Uani 1 2 d S T P . .
O2 O 0.8843(3) 0.0000 0.16996(18) 0.0813(13) Uani 1 2 d S T P . .
S1 S -0.27845(14) 0.0000 0.33505(10) 0.0970(6) Uani 1 2 d S T P . .
S2 S 0.77601(16) 0.0000 -0.13203(7) 0.0918(6) Uani 1 2 d S T P . .
Sn1 Sn 0.06585(3) 0.0000 0.29715(2) 0.05566(14) Uani 1 2 d S T P . .
Sn2 Sn 0.87412(3) 0.0000 0.06929(2) 0.05996(15) Uani 1 2 d S T P . .


_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 C6 1.371(8) . ?
C1 C2 1.380(8) . ?
C1 Sn1 2.150(6) . ?
C2 C3 1.390(9) . ?
C2 C7 1.459(9) . ?
C3 C4 1.369(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.193(8) . ?
C7 H7 0.9300 . ?
C8 Sn1 2.107(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.156(7) . ?
C9 S1 1.602(6) . ?
C11 C16 1.366(9) . ?
C11 C12 1.369(8) . ?
C11 Sn2 2.122(6) . ?
C12 C13 1.387(8) . ?
C12 C17 1.432(9) . ?
C13 C14 1.344(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.339(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.404(11) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O2 1.206(8) . ?
C17 H17 0.9300 . ?
C18 Sn2 2.107(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N2 1.162(8) . ?
C19 S2 1.594(7) . ?
N1 Sn1 2.164(5) . ?
N2 Sn2 2.161(6) . ?
O1 Sn1 2.468(4) . ?
O2 Sn2 2.442(4) . ?
Sn1 C8 2.107(4) 6 ?
Sn2 C18 2.107(4) 6 ?

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 C1 C2 118.8(6) . . ?
C6 C1 Sn1 125.2(5) . . ?
C2 C1 Sn1 116.0(4) . . ?
C1 C2 C3 121.1(6) . . ?
C1 C2 C7 117.7(6) . . ?
C3 C2 C7 121.2(6) . . ?
C4 C3 C2 119.8(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.9(7) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.4(7) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 120.1(6) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C2 123.9(6) . . ?
O1 C7 H7 118.1 . . ?
C2 C7 H7 118.1 . . ?
Sn1 C8 H8A 109.5 . . ?
Sn1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Sn1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 S1 178.3(6) . . ?
C16 C11 C12 116.6(6) . . ?
C16 C11 Sn2 126.5(5) . . ?
C12 C11 Sn2 117.0(4) . . ?
C11 C12 C13 123.2(6) . . ?
C11 C12 C17 116.9(5) . . ?
C13 C12 C17 119.9(6) . . ?
C14 C13 C12 119.7(7) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 118.2(7) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 123.1(8) . . ?
C14 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C11 C16 C15 119.2(8) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
O2 C17 C12 124.5(6) . . ?
O2 C17 H17 117.8 . . ?
C12 C17 H17 117.8 . . ?
Sn2 C18 H18A 109.5 . . ?
Sn2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Sn2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 S2 177.7(6) . . ?
C9 N1 Sn1 176.6(5) . . ?
C19 N2 Sn2 175.7(6) . . ?
C7 O1 Sn1 108.9(4) . . ?
C17 O2 Sn2 108.2(4) . . ?
C8 Sn1 C8 118.7(3) . 6 ?
C8 Sn1 C1 118.31(13) . . ?
C8 Sn1 C1 118.32(13) 6 . ?
C8 Sn1 N1 99.09(14) . . ?
C8 Sn1 N1 99.09(14) 6 . ?
C1 Sn1 N1 93.4(2) . . ?
C8 Sn1 O1 87.44(14) . . ?
C8 Sn1 O1 87.44(14) 6 . ?
C1 Sn1 O1 73.54(18) . . ?
N1 Sn1 O1 166.97(18) . . ?
C18 Sn2 C18 117.7(2) 6 . ?
C18 Sn2 C11 118.78(12) 6 . ?
C18 Sn2 C11 118.78(12) . . ?
C18 Sn2 N2 98.04(15) 6 . ?
C18 Sn2 N2 98.04(15) . . ?
C11 Sn2 N2 95.7(2) . . ?
C18 Sn2 O2 87.47(13) 6 . ?
C18 Sn2 O2 87.47(13) . . ?
C11 Sn2 O2 73.52(19) . . ?
N2 Sn2 O2 169.20(19) . . ?

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
C6 C1 C2 C3 0.000(2) . . . . ?
Sn1 C1 C2 C3 180.000(1) . . . . ?
C6 C1 C2 C7 180.000(1) . . . . ?
Sn1 C1 C2 C7 0.000(1) . . . . ?
C1 C2 C3 C4 0.000(2) . . . . ?
C7 C2 C3 C4 180.000(2) . . . . ?
C2 C3 C4 C5 0.000(2) . . . . ?
C3 C4 C5 C6 0.000(2) . . . . ?
C2 C1 C6 C5 0.000(2) . . . . ?
Sn1 C1 C6 C5 180.000(2) . . . . ?
C4 C5 C6 C1 0.000(2) . . . . ?
C1 C2 C7 O1 0.000(2) . . . . ?
C3 C2 C7 O1 180.000(1) . . . . ?
C16 C11 C12 C13 0.000(1) . . . . ?
Sn2 C11 C12 C13 180.000(1) . . . . ?
C16 C11 C12 C17 180.000(1) . . . . ?
Sn2 C11 C12 C17 0.000(1) . . . . ?
C11 C12 C13 C14 0.000(1) . . . . ?
C17 C12 C13 C14 180.000(1) . . . . ?
C12 C13 C14 C15 0.000(1) . . . . ?
C13 C14 C15 C16 0.000(1) . . . . ?
C12 C11 C16 C15 0.000(0) . . . . ?
Sn2 C11 C16 C15 180.000(0) . . . . ?
C14 C15 C16 C11 0.000(0) . . . . ?
C11 C12 C17 O2 0.000(1) . . . . ?
C13 C12 C17 O2 180.000(1) . . . . ?
C2 C7 O1 Sn1 0.000(1) . . . . ?
C12 C17 O2 Sn2 0.000(1) . . . . ?

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_685r
_database_code_depnum_ccdc_archive 'CCDC 1860611'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultatea de Chimie si Inginerie Chimica,  Universitatea Babes-Bolyai
Romania
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 Cl2 N2 Sn2'
_chemical_formula_sum            'C30 H30 Cl2 N2 Sn2'
_chemical_formula_weight         726.84

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'
Cl Cl 0.1484 0.1585 '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                   7.340(3)
_cell_length_b                   12.824(5)
_cell_length_c                   15.719(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.371(6)
_cell_angle_gamma                90
_cell_volume                     1470.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3207
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      21.47
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.901
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_T_max  0.7259
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(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_reflns_number            12709
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.608
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2565
_reflns_number_gt                2245
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0420P)²+1.1525P] 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         2565
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_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
C1 C 0.0775(7) 0.7438(4) 0.8077(3) 0.0508(13) Uani 1 1 d . . . . .
C2 C 0.1622(7) 0.7780(4) 0.8854(4) 0.0543(14) Uani 1 1 d . . . . .
C3 C 0.0862(9) 0.8556(5) 0.9304(5) 0.077(2) Uani 1 1 d . . . . .
H3 H 0.1455 0.8769 0.9829 0.093 Uiso 1 1 calc R U . . .
C4 C -0.0762(10) 0.9021(5) 0.8990(6) 0.088(2) Uani 1 1 d . . . . .
H4 H -0.1270 0.9552 0.9291 0.106 Uiso 1 1 calc R U . . .
C5 C -0.1607(10) 0.8679(5) 0.8224(6) 0.092(2) Uani 1 1 d . . . . .
H5 H -0.2712 0.8983 0.8007 0.110 Uiso 1 1 calc R U . . .
C6 C -0.0880(8) 0.7896(5) 0.7757(4) 0.0699(17) Uani 1 1 d . . . . .
H6 H -0.1490 0.7679 0.7237 0.084 Uiso 1 1 calc R U . . .
C7 C 0.3345(7) 0.7304(4) 0.9204(4) 0.0590(15) Uani 1 1 d . . . . .
H7 H 0.3931 0.7542 0.9723 0.071 Uiso 1 1 calc R U . . .
C10 C 0.5771(7) 0.6144(4) 0.9168(3) 0.0491(13) Uani 1 1 d . . . . .
C11 C 0.6199(8) 0.5141(5) 0.8962(4) 0.076(2) Uani 1 1 d . . . . .
H11 H 0.5372 0.4753 0.8598 0.091 Uiso 1 1 calc R U . . .
C12 C 0.7846(8) 0.4704(5) 0.9289(4) 0.0734(19) Uani 1 1 d . . . . .
H12 H 0.8100 0.4021 0.9144 0.088 Uiso 1 1 calc R U . . .
C13 C 0.9119(6) 0.5241(4) 0.9820(3) 0.0443(12) Uani 1 1 d . . . . .
C14 C 0.8689(8) 0.6246(4) 0.9993(4) 0.0559(15) Uani 1 1 d . . . . .
H14 H 0.9529 0.6644 1.0341 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7056(7) 0.6692(5) 0.9671(4) 0.0568(14) Uani 1 1 d . . . . .
H15 H 0.6826 0.7384 0.9800 0.068 Uiso 1 1 calc R U . . .
C9 C 0.4396(9) 0.6661(5) 0.6818(4) 0.0728(18) Uani 1 1 d . . . . .
H9A H 0.5477 0.6322 0.7087 0.109 Uiso 1 1 calc R U . . .
H9B H 0.4558 0.7403 0.6851 0.109 Uiso 1 1 calc R U . . .
H9C H 0.4190 0.6453 0.6229 0.109 Uiso 1 1 calc R U . . .
C8 C 0.1676(8) 0.4670(4) 0.7791(4) 0.0642(16) Uani 1 1 d . . . . .
H8A H 0.1915 0.4219 0.7329 0.096 Uiso 1 1 calc R U . . .
H8B H 0.0427 0.4585 0.7907 0.096 Uiso 1 1 calc R U . . .
H8C H 0.2484 0.4495 0.8293 0.096 Uiso 1 1 calc R U . . .
Cl1 Cl -0.0144(3) 0.61613(16) 0.61522(12) 0.0957(7) Uani 1 1 d . . . . .
N1 N 0.4054(6) 0.6576(4) 0.8816(3) 0.0496(11) Uani 1 1 d . . . . .
Sn1 Sn 0.21174(5) 0.62303(3) 0.74506(2) 0.05015(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(7) . ?
C1 C6 1.393(7) . ?
C1 Sn1 2.134(6) . ?
C2 C3 1.375(8) . ?
C2 C7 1.456(7) . ?
C3 C4 1.375(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.259(6) . ?
C7 H7 0.9300 . ?
C10 C15 1.357(7) . ?
C10 C11 1.372(7) . ?
C10 N1 1.431(6) . ?
C11 C12 1.379(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(7) . ?
C13 C13 1.488(9) 3_767 ?
C14 C15 1.373(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C9 Sn1 2.112(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 Sn1 2.105(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
Cl1 Sn1 2.4854(18) . ?
N1 Sn1 2.479(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
C2 C1 C6 118.4(5) . . ?
C2 C1 Sn1 117.0(4) . . ?
C6 C1 Sn1 124.6(4) . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 C7 119.5(5) . . ?
C1 C2 C7 119.3(5) . . ?
C4 C3 C2 120.9(7) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 118.0(7) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 122.5(6) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 119.1(6) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C2 121.0(5) . . ?
N1 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C15 C10 C11 117.4(5) . . ?
C15 C10 N1 123.4(5) . . ?
C11 C10 N1 119.1(5) . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 122.3(6) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C14 C13 C12 116.1(5) . . ?
C14 C13 C13 121.9(6) . 3_767 ?
C12 C13 C13 121.9(6) . 3_767 ?
C13 C14 C15 122.2(5) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 121.4(5) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
Sn1 C9 H9A 109.5 . . ?
Sn1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Sn1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Sn1 C8 H8A 109.5 . . ?
Sn1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Sn1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 N1 C10 119.5(4) . . ?
C7 N1 Sn1 108.9(3) . . ?
C10 N1 Sn1 131.4(3) . . ?
C8 Sn1 C9 121.4(3) . . ?
C8 Sn1 C1 118.7(2) . . ?
C9 Sn1 C1 117.3(2) . . ?
C8 Sn1 N1 92.2(2) . . ?
C9 Sn1 N1 87.3(2) . . ?
C1 Sn1 N1 73.77(17) . . ?
C8 Sn1 Cl1 93.86(17) . . ?
C9 Sn1 Cl1 96.58(19) . . ?
C1 Sn1 Cl1 95.98(15) . . ?
N1 Sn1 Cl1 169.68(11) . . ?

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
C6 C1 C2 C3 -0.1(9) . . . . ?
Sn1 C1 C2 C3 179.9(5) . . . . ?
C6 C1 C2 C7 179.4(5) . . . . ?
Sn1 C1 C2 C7 -0.6(7) . . . . ?
C1 C2 C3 C4 -0.5(10) . . . . ?
C7 C2 C3 C4 179.9(7) . . . . ?
C2 C3 C4 C5 0.8(12) . . . . ?
C3 C4 C5 C6 -0.5(12) . . . . ?
C4 C5 C6 C1 -0.1(11) . . . . ?
C2 C1 C6 C5 0.4(9) . . . . ?
Sn1 C1 C6 C5 -179.6(5) . . . . ?
C3 C2 C7 N1 178.4(6) . . . . ?
C1 C2 C7 N1 -1.2(9) . . . . ?
C15 C10 C11 C12 2.8(10) . . . . ?
N1 C10 C11 C12 179.8(6) . . . . ?
C10 C11 C12 C13 -0.6(11) . . . . ?
C11 C12 C13 C14 -1.6(10) . . . . ?
C11 C12 C13 C13 179.2(7) . . . 3_767 ?
C12 C13 C14 C15 1.5(9) . . . . ?
C13 C13 C14 C15 -179.3(6) 3_767 . . . ?
C11 C10 C15 C14 -2.9(9) . . . . ?
N1 C10 C15 C14 -179.8(5) . . . . ?
C13 C14 C15 C10 0.8(9) . . . . ?
C2 C7 N1 C10 178.4(5) . . . . ?
C2 C7 N1 Sn1 2.0(7) . . . . ?
C15 C10 N1 C7 -28.2(8) . . . . ?
C11 C10 N1 C7 154.9(6) . . . . ?
C15 C10 N1 Sn1 147.3(5) . . . . ?
C11 C10 N1 Sn1 -29.6(8) . . . . ?

_refine_diff_density_max         0.632
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_739r
_database_code_depnum_ccdc_archive 'CCDC 1860609'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultatea de Chimie si Inginerie Chimica,  Universitatea Babes-Bolyai
Romania
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N O S Sn'
_chemical_formula_weight         311.95

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                   7.3830(16)
_cell_length_b                   11.922(3)
_cell_length_c                   15.542(3)
_cell_angle_alpha                68.185(4)
_cell_angle_beta                 80.788(4)
_cell_angle_gamma                81.019(4)
_cell_volume                     1246.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2053
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      19.58
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.187
_shelx_estimated_absorpt_T_min   0.580
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5796
_exptl_absorpt_correction_T_max  0.8110
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '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_reflns_number            11889
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.420
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_full        25.015
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4378
_reflns_number_gt                3082
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0338P)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         4378
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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
C1 C 0.3678(7) 0.8269(5) 0.3153(4) 0.0563(14) Uani 1 1 d . . . . .
C2 C 0.3388(8) 0.7348(7) 0.4015(4) 0.0686(17) Uani 1 1 d . . . . .
C3 C 0.3625(9) 0.6126(7) 0.4101(5) 0.087(2) Uani 1 1 d . . . . .
H3 H 0.3428 0.5519 0.4683 0.104 Uiso 1 1 calc R U . . .
C4 C 0.4152(9) 0.5835(7) 0.3318(6) 0.089(2) Uani 1 1 d . . . . .
H4 H 0.4293 0.5027 0.3364 0.107 Uiso 1 1 calc R U . . .
C5 C 0.4466(8) 0.6719(7) 0.2482(5) 0.0773(19) Uani 1 1 d . . . . .
H5 H 0.4872 0.6508 0.1959 0.093 Uiso 1 1 calc R U . . .
C6 C 0.4201(7) 0.7929(6) 0.2385(4) 0.0625(15) Uani 1 1 d . . . . .
H6 H 0.4376 0.8521 0.1796 0.075 Uiso 1 1 calc R U . . .
C7 C 0.2830(10) 0.7729(8) 0.4835(5) 0.097(3) Uani 1 1 d . . . . .
H7 H 0.2629 0.7130 0.5420 0.116 Uiso 1 1 calc R U . . .
C8 C 0.0484(8) 1.0894(6) 0.3244(5) 0.099(2) Uani 1 1 d . . . . .
H8A H -0.0104 1.0911 0.2730 0.148 Uiso 1 1 calc R U . . .
H8B H 0.0487 1.1708 0.3223 0.148 Uiso 1 1 calc R U . . .
H8C H -0.0178 1.0432 0.3820 0.148 Uiso 1 1 calc R U . . .
C9 C 0.5339(9) 1.0778(7) 0.3512(5) 0.102(2) Uani 1 1 d . . . . .
H9A H 0.5823 1.0184 0.4059 0.153 Uiso 1 1 calc R U . . .
H9B H 0.4843 1.1503 0.3636 0.153 Uiso 1 1 calc R U . . .
H9C H 0.6309 1.0963 0.3006 0.153 Uiso 1 1 calc R U . . .
C10 C 0.4792(9) 1.1417(5) 0.0982(5) 0.0685(17) Uani 1 1 d . . . . .
C11 C 0.9472(7) 0.6760(5) 0.1842(4) 0.0580(15) Uani 1 1 d . . . . .
C12 C 0.9088(7) 0.7696(6) 0.1006(4) 0.0595(15) Uani 1 1 d . . . . .
C13 C 0.8637(8) 0.8888(6) 0.0959(4) 0.0675(16) Uani 1 1 d . . . . .
H13 H 0.8362 0.9496 0.0399 0.081 Uiso 1 1 calc R U . . .
C14 C 0.8600(8) 0.9170(6) 0.1752(5) 0.0746(18) Uani 1 1 d . . . . .
H14 H 0.8311 0.9968 0.1727 0.090 Uiso 1 1 calc R U . . .
C15 C 0.8990(8) 0.8265(7) 0.2565(5) 0.0751(18) Uani 1 1 d . . . . .
H15 H 0.8984 0.8461 0.3092 0.090 Uiso 1 1 calc R U . . .
C16 C 0.9394(8) 0.7065(6) 0.2634(4) 0.0655(16) Uani 1 1 d . . . . .
H16 H 0.9613 0.6463 0.3205 0.079 Uiso 1 1 calc R U . . .
C17 C 0.9172(8) 0.7361(7) 0.0192(4) 0.0743(18) Uani 1 1 d . . . . .
H17 H 0.8944 0.7977 -0.0371 0.089 Uiso 1 1 calc R U . . .
C18 C 1.2758(8) 0.4477(6) 0.1247(5) 0.095(2) Uani 1 1 d . . . . .
H18A H 1.3059 0.3616 0.1532 0.142 Uiso 1 1 calc R U . . .
H18B H 1.3627 0.4895 0.1381 0.142 Uiso 1 1 calc R U . . .
H18C H 1.2812 0.4693 0.0584 0.142 Uiso 1 1 calc R U . . .
C19 C 0.7826(8) 0.4066(6) 0.1810(5) 0.090(2) Uani 1 1 d . . . . .
H19A H 0.7230 0.3761 0.2435 0.134 Uiso 1 1 calc R U . . .
H19B H 0.8262 0.3401 0.1597 0.134 Uiso 1 1 calc R U . . .
H19C H 0.6962 0.4620 0.1409 0.134 Uiso 1 1 calc R U . . .
C20 C 1.1150(9) 0.3562(6) 0.3920(5) 0.0736(18) Uani 1 1 d . . . . .
N1 N 0.3880(8) 1.0922(5) 0.1651(4) 0.0882(17) Uani 1 1 d . . . . .
N2 N 1.0470(8) 0.4088(5) 0.3254(4) 0.0931(19) Uani 1 1 d . . . . .
O1 O 0.2625(7) 0.8775(5) 0.4782(3) 0.0965(17) Uani 1 1 d . . . . .
O2 O 0.9520(6) 0.6327(4) 0.0196(3) 0.0813(13) Uani 1 1 d . . . . .
S1 S 0.5993(3) 1.2089(2) 0.00451(14) 0.1174(8) Uani 1 1 d . . . . .
S2 S 1.2060(3) 0.2840(2) 0.48580(14) 0.1139(8) Uani 1 1 d . . . . .
Sn1 Sn 0.32306(5) 1.00795(4) 0.31518(3) 0.06333(16) Uani 1 1 d . . . . .
Sn2 Sn 1.00722(5) 0.49772(4) 0.17832(3) 0.06498(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.379(7) . ?
C1 C2 1.391(7) . ?
C1 Sn1 2.131(6) . ?
C2 C3 1.399(9) . ?
C2 C7 1.485(10) . ?
C3 C4 1.368(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.347(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.206(8) . ?
C7 H7 0.9300 . ?
C8 Sn1 2.114(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 Sn1 2.112(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.152(7) . ?
C10 S1 1.578(7) . ?
C11 C16 1.398(7) . ?
C11 C12 1.398(7) . ?
C11 Sn2 2.136(6) . ?
C12 C13 1.385(7) . ?
C12 C17 1.452(8) . ?
C13 C14 1.388(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O2 1.217(7) . ?
C17 H17 0.9300 . ?
C18 Sn2 2.111(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 Sn2 2.107(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N2 1.142(7) . ?
C20 S2 1.586(7) . ?
N1 Sn1 2.174(6) . ?
N2 Sn2 2.180(6) . ?
O1 Sn1 2.442(5) . ?
O2 Sn2 2.451(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
C6 C1 C2 117.3(6) . . ?
C6 C1 Sn1 126.4(4) . . ?
C2 C1 Sn1 116.3(5) . . ?
C1 C2 C3 121.4(6) . . ?
C1 C2 C7 116.7(7) . . ?
C3 C2 C7 121.9(7) . . ?
C4 C3 C2 119.0(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 120.0(7) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.5(7) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 120.7(6) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C7 C2 123.3(7) . . ?
O1 C7 H7 118.3 . . ?
C2 C7 H7 118.3 . . ?
Sn1 C8 H8A 109.5 . . ?
Sn1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Sn1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Sn1 C9 H9A 109.5 . . ?
Sn1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Sn1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 S1 178.0(7) . . ?
C16 C11 C12 117.9(5) . . ?
C16 C11 Sn2 126.2(4) . . ?
C12 C11 Sn2 116.0(4) . . ?
C13 C12 C11 121.4(6) . . ?
C13 C12 C17 121.6(6) . . ?
C11 C12 C17 117.0(6) . . ?
C12 C13 C14 119.6(6) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 119.3(6) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 122.1(6) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C16 C11 119.7(6) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
O2 C17 C12 124.4(6) . . ?
O2 C17 H17 117.8 . . ?
C12 C17 H17 117.8 . . ?
Sn2 C18 H18A 109.5 . . ?
Sn2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Sn2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Sn2 C19 H19A 109.5 . . ?
Sn2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Sn2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 S2 178.8(7) . . ?
C10 N1 Sn1 154.5(6) . . ?
C20 N2 Sn2 161.4(6) . . ?
C7 O1 Sn1 109.1(5) . . ?
C17 O2 Sn2 108.2(4) . . ?
C9 Sn1 C8 119.5(3) . . ?
C9 Sn1 C1 119.0(2) . . ?
C8 Sn1 C1 118.3(2) . . ?
C9 Sn1 N1 95.8(2) . . ?
C8 Sn1 N1 97.4(3) . . ?
C1 Sn1 N1 94.7(2) . . ?
C9 Sn1 O1 89.5(2) . . ?
C8 Sn1 O1 88.0(2) . . ?
C1 Sn1 O1 74.6(2) . . ?
N1 Sn1 O1 169.2(2) . . ?
C19 Sn2 C18 121.1(2) . . ?
C19 Sn2 C11 117.5(2) . . ?
C18 Sn2 C11 118.0(2) . . ?
C19 Sn2 N2 97.0(2) . . ?
C18 Sn2 N2 96.7(2) . . ?
C11 Sn2 N2 94.8(2) . . ?
C19 Sn2 O2 88.3(2) . . ?
C18 Sn2 O2 88.4(2) . . ?
C11 Sn2 O2 74.42(19) . . ?
N2 Sn2 O2 169.27(18) . . ?

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
C6 C1 C2 C3 0.3(8) . . . . ?
Sn1 C1 C2 C3 179.5(4) . . . . ?
C6 C1 C2 C7 179.8(5) . . . . ?
Sn1 C1 C2 C7 -0.9(7) . . . . ?
C1 C2 C3 C4 -0.1(9) . . . . ?
C7 C2 C3 C4 -179.6(6) . . . . ?
C2 C3 C4 C5 1.2(10) . . . . ?
C3 C4 C5 C6 -2.6(10) . . . . ?
C2 C1 C6 C5 -1.6(8) . . . . ?
Sn1 C1 C6 C5 179.2(4) . . . . ?
C4 C5 C6 C1 2.8(9) . . . . ?
C1 C2 C7 O1 0.1(10) . . . . ?
C3 C2 C7 O1 179.6(7) . . . . ?
C16 C11 C12 C13 -0.2(8) . . . . ?
Sn2 C11 C12 C13 178.5(4) . . . . ?
C16 C11 C12 C17 -179.8(5) . . . . ?
Sn2 C11 C12 C17 -1.1(7) . . . . ?
C11 C12 C13 C14 1.3(9) . . . . ?
C17 C12 C13 C14 -179.1(5) . . . . ?
C12 C13 C14 C15 -0.6(9) . . . . ?
C13 C14 C15 C16 -1.1(9) . . . . ?
C14 C15 C16 C11 2.2(9) . . . . ?
C12 C11 C16 C15 -1.5(8) . . . . ?
Sn2 C11 C16 C15 179.9(4) . . . . ?
C13 C12 C17 O2 -178.3(6) . . . . ?
C11 C12 C17 O2 1.3(9) . . . . ?
C2 C7 O1 Sn1 0.7(9) . . . . ?
C12 C17 O2 Sn2 -0.7(7) . . . . ?

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_757r
_database_code_depnum_ccdc_archive 'CCDC 1860613'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultatea de Chimie si Inginerie Chimica,  Universitatea Babes-Bolyai
Romania
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2015/1
_shelx_SHELXL_version_number     2015/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H45 Cl2 N5 O3 Sn Zn'
_chemical_formula_weight         1138.97

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'
Zn Zn 0.2839 1.4301 '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'
Cl Cl 0.1484 0.1585 '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                   21.938(4)
_cell_length_b                   11.1466(18)
_cell_length_c                   21.982(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.914(3)
_cell_angle_gamma                90
_cell_volume                     5346.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2126
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      20.03
_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             2312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.065
_shelx_estimated_absorpt_T_min   0.675
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_process_details   'Bruker, 2001.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '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_reflns_number            26981
_diffrn_reflns_av_unetI/netI     0.1130
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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             9376
_reflns_number_gt                6270
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2015/1 (Sheldrick, 2015)'
_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)+(0.1151P)²+27.1238P] 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         9376
_refine_ls_number_parameters     652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1902
_refine_ls_wR_factor_gt          0.1576
_refine_ls_goodness_of_fit_ref   0.785
_refine_ls_restrained_S_all      0.785
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4041(3) 0.8722(6) 0.1661(3) 0.0322(16) Uani 1 1 d . . . . .
C2 C 0.3540(3) 0.8468(7) 0.1220(3) 0.0435(19) Uani 1 1 d . . . . .
C3 C 0.3068(4) 0.7673(8) 0.1346(4) 0.055(2) Uani 1 1 d . . . . .
H3 H 0.2744 0.7524 0.1049 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3083(4) 0.7120(8) 0.1905(4) 0.060(2) Uani 1 1 d . . . . .
H4 H 0.2782 0.6571 0.1986 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3559(4) 0.7403(7) 0.2344(4) 0.050(2) Uani 1 1 d . . . . .
H5 H 0.3564 0.7059 0.2730 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4039(4) 0.8197(6) 0.2229(3) 0.0414(18) Uani 1 1 d . . . . .
H6 H 0.4352 0.8363 0.2536 0.050 Uiso 1 1 calc R U . . .
C7 C 0.3516(4) 0.9060(9) 0.0632(4) 0.058(2) Uani 1 1 d . . . . .
H7 H 0.3192 0.8879 0.0340 0.070 Uiso 1 1 calc R U . . .
C8 C 0.5310(4) 0.8959(9) 0.0759(4) 0.065(3) Uani 1 1 d . . . . .
H8A H 0.5061 0.8429 0.0495 0.097 Uiso 1 1 calc R U . . .
H8B H 0.5623 0.8506 0.0994 0.097 Uiso 1 1 calc R U . . .
H8C H 0.5497 0.9545 0.0517 0.097 Uiso 1 1 calc R U . . .
C9 C 0.4629(4) 1.1734(7) 0.1336(4) 0.059(2) Uani 1 1 d . . . . .
H9A H 0.4828 1.2066 0.1005 0.089 Uiso 1 1 calc R U . . .
H9B H 0.4802 1.2076 0.1715 0.089 Uiso 1 1 calc R U . . .
H9C H 0.4199 1.1913 0.1275 0.089 Uiso 1 1 calc R U . . .
C10 C 0.5325(3) 1.0087(6) 0.2630(3) 0.0323(16) Uani 1 1 d . . . . .
C11 C 0.5829(3) 0.9873(6) 0.3142(3) 0.0325(16) Uani 1 1 d . . . . .
C12 C 0.5708(3) 1.0070(7) 0.3735(3) 0.0388(18) Uani 1 1 d . . . . .
H12 H 0.5336 1.0393 0.3822 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6155(3) 0.9776(7) 0.4197(3) 0.0423(19) Uani 1 1 d . . . . .
H13 H 0.6070 0.9905 0.4598 0.051 Uiso 1 1 calc R U . . .
C14 C 0.6825(3) 0.9130(7) 0.3539(3) 0.0388(18) Uani 1 1 d . . . . .
H14 H 0.7203 0.8813 0.3466 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6396(3) 0.9400(7) 0.3043(3) 0.0375(17) Uani 1 1 d . . . . .
H15 H 0.6490 0.9262 0.2646 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6469(3) 0.8629(6) 0.5902(3) 0.0275(15) Uani 1 1 d . . . . .
C17 C 0.6295(3) 0.9384(6) 0.6385(3) 0.0308(16) Uani 1 1 d . . . . .
H17 H 0.5994 0.9218 0.6643 0.037 Uiso 1 1 calc R U . . .
C18 C 0.6647(3) 1.0377(6) 0.6397(3) 0.0308(16) Uani 1 1 d . . . . .
H18 H 0.6634 1.1021 0.6664 0.037 Uiso 1 1 calc R U . . .
C19 C 0.7046(3) 1.0260(6) 0.5920(3) 0.0250(14) Uani 1 1 d . . . . .
C20 C 0.7507(3) 1.1112(6) 0.5798(3) 0.0299(15) Uani 1 1 d . . . . .
C21 C 0.7925(3) 1.0990(6) 0.5352(3) 0.0256(14) Uani 1 1 d . . . . .
C22 C 0.8382(3) 1.1852(6) 0.5228(3) 0.0365(17) Uani 1 1 d . . . . .
H22 H 0.8442 1.2599 0.5412 0.044 Uiso 1 1 calc R U . . .
C23 C 0.8706(3) 1.1389(6) 0.4799(4) 0.0405(18) Uani 1 1 d . . . . .
H23 H 0.9033 1.1751 0.4632 0.049 Uiso 1 1 calc R U . . .
C24 C 0.8448(3) 1.0219(6) 0.4647(3) 0.0318(16) Uani 1 1 d . . . . .
C25 C 0.8676(3) 0.9412(6) 0.4231(3) 0.0315(16) Uani 1 1 d . . . . .
C26 C 0.8438(3) 0.8272(6) 0.4090(3) 0.0338(16) Uani 1 1 d . . . . .
C27 C 0.8669(3) 0.7443(6) 0.3658(3) 0.0353(17) Uani 1 1 d . . . . .
H27 H 0.9003 0.7571 0.3438 0.042 Uiso 1 1 calc R U . . .
C28 C 0.8315(3) 0.6461(7) 0.3635(3) 0.0377(17) Uani 1 1 d . . . . .
H28 H 0.8360 0.5782 0.3397 0.045 Uiso 1 1 calc R U . . .
C29 C 0.7846(3) 0.6648(6) 0.4047(3) 0.0295(16) Uani 1 1 d . . . . .
C30 C 0.7371(3) 0.5818(6) 0.4150(3) 0.0321(16) Uani 1 1 d . . . . .
C31 C 0.6945(3) 0.5959(6) 0.4585(3) 0.0314(16) Uani 1 1 d . . . . .
C32 C 0.6497(3) 0.5080(6) 0.4726(3) 0.0383(18) Uani 1 1 d . . . . .
H32 H 0.6432 0.4338 0.4538 0.046 Uiso 1 1 calc R U . . .
C33 C 0.6190(3) 0.5518(7) 0.5176(3) 0.0407(18) Uani 1 1 d . . . . .
H33 H 0.5880 0.5134 0.5360 0.049 Uiso 1 1 calc R U . . .
C34 C 0.6434(3) 0.6697(6) 0.5319(3) 0.0296(15) Uani 1 1 d . . . . .
C35 C 0.6238(3) 0.7481(6) 0.5765(3) 0.0299(16) Uani 1 1 d . . . . .
C36 C 0.7566(3) 1.2224(6) 0.6180(3) 0.0293(15) Uani 1 1 d . . . . .
C37 C 0.7209(4) 1.3238(7) 0.6031(4) 0.048(2) Uani 1 1 d . . . . .
H37 H 0.6912 1.3221 0.5697 0.057 Uiso 1 1 calc R U . . .
C38 C 0.7297(4) 1.4272(7) 0.6380(4) 0.055(2) Uani 1 1 d . . . . .
H38 H 0.7058 1.4945 0.6277 0.066 Uiso 1 1 calc R U . . .
C39 C 0.7735(4) 1.4317(7) 0.6879(4) 0.052(2) Uani 1 1 d . . . . .
H39 H 0.7792 1.5012 0.7112 0.062 Uiso 1 1 calc R U . . .
C40 C 0.8082(4) 1.3318(8) 0.7023(4) 0.052(2) Uani 1 1 d . . . . .
H40 H 0.8379 1.3341 0.7357 0.063 Uiso 1 1 calc R U . . .
C41 C 0.8002(4) 1.2281(7) 0.6686(4) 0.049(2) Uani 1 1 d . . . . .
H41 H 0.8241 1.1612 0.6798 0.058 Uiso 1 1 calc R U . . .
C42 C 0.9227(4) 0.9843(7) 0.3932(3) 0.0415(19) Uani 1 1 d . . . . .
C43 C 0.9162(4) 1.0579(9) 0.3433(4) 0.063(3) Uani 1 1 d . . . . .
H43 H 0.8774 1.0785 0.3253 0.075 Uiso 1 1 calc R U . . .
C44 C 0.9708(5) 1.1036(10) 0.3188(4) 0.076(3) Uani 1 1 d . . . . .
H44 H 0.9669 1.1535 0.2847 0.091 Uiso 1 1 calc R U . . .
C45 C 1.0277(5) 1.0736(9) 0.3456(5) 0.069(3) Uani 1 1 d . . . . .
H45 H 1.0622 1.1041 0.3298 0.083 Uiso 1 1 calc R U . . .
C46 C 1.0346(4) 1.0000(8) 0.3949(5) 0.065(3) Uani 1 1 d . . . . .
H46 H 1.0735 0.9789 0.4124 0.078 Uiso 1 1 calc R U . . .
C47 C 0.9827(4) 0.9563(8) 0.4191(4) 0.053(2) Uani 1 1 d . . . . .
H47 H 0.9877 0.9070 0.4534 0.064 Uiso 1 1 calc R U . . .
C48 C 0.7328(3) 0.4697(6) 0.3775(3) 0.0364(17) Uani 1 1 d . . . . .
C49 C 0.7062(4) 0.4739(7) 0.3177(4) 0.050(2) Uani 1 1 d . . . . .
H49 H 0.6912 0.5465 0.3015 0.060 Uiso 1 1 calc R U . . .
C50 C 0.7014(5) 0.3713(9) 0.2813(4) 0.068(3) Uani 1 1 d . . . . .
H50 H 0.6846 0.3760 0.2408 0.082 Uiso 1 1 calc R U . . .
C51 C 0.7217(5) 0.2636(9) 0.3054(5) 0.071(3) Uani 1 1 d . . . . .
H51 H 0.7182 0.1947 0.2814 0.086 Uiso 1 1 calc R U . . .
C52 C 0.7470(6) 0.2571(8) 0.3646(6) 0.097(4) Uani 1 1 d . . . . .
H52 H 0.7606 0.1837 0.3809 0.116 Uiso 1 1 calc R U . . .
C53 C 0.7527(5) 0.3591(8) 0.4006(4) 0.075(3) Uani 1 1 d . . . . .
H53 H 0.7701 0.3533 0.4409 0.090 Uiso 1 1 calc R U . . .
C54 C 0.5742(3) 0.7021(6) 0.6139(4) 0.0368(17) Uani 1 1 d . . . . .
C55 C 0.5115(4) 0.7123(7) 0.5963(4) 0.052(2) Uani 1 1 d . . . . .
H55 H 0.4982 0.7436 0.5580 0.062 Uiso 1 1 calc R U . . .
C56 C 0.4679(4) 0.6765(9) 0.6352(5) 0.064(3) Uani 1 1 d . . . . .
H56 H 0.4263 0.6844 0.6228 0.077 Uiso 1 1 calc R U . . .
C57 C 0.4874(6) 0.6297(9) 0.6914(5) 0.078(3) Uani 1 1 d . . . . .
H57 H 0.4589 0.6074 0.7178 0.093 Uiso 1 1 calc R U . . .
C58 C 0.5498(5) 0.6154(9) 0.7093(5) 0.076(3) Uani 1 1 d . . . . .
H58 H 0.5625 0.5807 0.7470 0.091 Uiso 1 1 calc R U . . .
C59 C 0.5930(4) 0.6523(7) 0.6717(4) 0.056(2) Uani 1 1 d . . . . .
H59 H 0.6345 0.6442 0.6846 0.067 Uiso 1 1 calc R U . . .
C60 C 0.5042(5) 0.6474(11) 0.3953(6) 0.104(4) Uani 1 1 d . . . . .
H60A H 0.4816 0.5792 0.3772 0.125 Uiso 1 1 calc R U . . .
H60B H 0.5241 0.6214 0.4345 0.125 Uiso 1 1 calc R U . . .
CL1 Cl 0.56065(15) 0.6834(3) 0.34901(15) 0.0947(9) Uani 1 1 d . . . . .
CL2 Cl 0.45279(15) 0.7567(3) 0.40829(19) 0.1158(12) Uani 1 1 d . . . . .
N1 N 0.6708(2) 0.9314(5) 0.4112(2) 0.0291(13) Uani 1 1 d . . . . .
N2 N 0.6928(2) 0.9194(5) 0.5622(2) 0.0248(12) Uani 1 1 d . . . . .
N3 N 0.7967(3) 0.9999(5) 0.4988(2) 0.0287(13) Uani 1 1 d . . . . .
N4 N 0.7933(2) 0.7746(5) 0.4319(2) 0.0290(13) Uani 1 1 d . . . . .
N5 N 0.6900(2) 0.6954(5) 0.4950(2) 0.0299(13) Uani 1 1 d . . . . .
O1 O 0.3895(3) 0.9777(6) 0.0501(3) 0.0627(17) Uani 1 1 d . . . . .
O2 O 0.5451(2) 0.9664(5) 0.2100(2) 0.0402(12) Uani 1 1 d . . . . .
O3 O 0.4840(2) 1.0592(5) 0.2711(2) 0.0456(13) Uani 1 1 d . . . . .
SN1 Sn 0.47541(2) 0.98447(5) 0.13600(2) 0.03520(18) Uani 1 1 d . . . . .
ZN1 Zn 0.73295(3) 0.86097(7) 0.48537(3) 0.0257(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.379(10) . ?
C1 C2 1.418(10) . ?
C1 SN1 2.159(7) . ?
C2 C3 1.412(11) . ?
C2 C7 1.447(11) . ?
C3 C4 1.371(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.419(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.209(10) . ?
C7 H7 0.9300 . ?
C8 SN1 2.131(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 SN1 2.123(8) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O3 1.233(8) . ?
C10 O2 1.312(8) . ?
C10 C11 1.514(9) . ?
C11 C12 1.374(10) . ?
C11 C15 1.388(10) . ?
C12 C13 1.377(10) . ?
C12 H12 0.9300 . ?
C13 N1 1.349(9) . ?
C13 H13 0.9300 . ?
C14 N1 1.325(9) . ?
C14 C15 1.399(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N2 1.384(8) . ?
C16 C35 1.397(9) . ?
C16 C17 1.438(9) . ?
C17 C18 1.348(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.440(9) . ?
C18 H18 0.9300 . ?
C19 N2 1.368(8) . ?
C19 C20 1.432(9) . ?
C20 C21 1.416(9) . ?
C20 C36 1.496(9) . ?
C21 N3 1.373(8) . ?
C21 C22 1.434(9) . ?
C22 C23 1.341(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.447(9) . ?
C23 H23 0.9300 . ?
C24 N3 1.379(8) . ?
C24 C25 1.410(9) . ?
C25 C26 1.396(10) . ?
C25 C42 1.512(10) . ?
C26 N4 1.392(9) . ?
C26 C27 1.454(9) . ?
C27 C28 1.340(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.455(10) . ?
C28 H28 0.9300 . ?
C29 N4 1.366(8) . ?
C29 C30 1.429(10) . ?
C30 C31 1.415(10) . ?
C30 C48 1.494(9) . ?
C31 N5 1.378(8) . ?
C31 C32 1.443(10) . ?
C32 C33 1.345(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.442(9) . ?
C33 H33 0.9300 . ?
C34 N5 1.400(9) . ?
C34 C35 1.413(9) . ?
C35 C54 1.517(9) . ?
C36 C41 1.393(10) . ?
C36 C37 1.394(10) . ?
C37 C38 1.388(11) . ?
C37 H37 0.9300 . ?
C38 C39 1.382(12) . ?
C38 H38 0.9300 . ?
C39 C40 1.368(12) . ?
C39 H39 0.9300 . ?
C40 C41 1.373(10) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 C43 1.365(11) . ?
C42 C47 1.413(11) . ?
C43 C44 1.455(12) . ?
C43 H43 0.9300 . ?
C44 C45 1.367(14) . ?
C44 H44 0.9300 . ?
C45 C46 1.355(14) . ?
C45 H45 0.9300 . ?
C46 C47 1.393(11) . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?
C48 C49 1.384(10) . ?
C48 C53 1.387(11) . ?
C49 C50 1.394(11) . ?
C49 H49 0.9300 . ?
C50 C51 1.368(13) . ?
C50 H50 0.9300 . ?
C51 C52 1.362(14) . ?
C51 H51 0.9300 . ?
C52 C53 1.383(13) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?
C54 C55 1.396(10) . ?
C54 C59 1.409(11) . ?
C55 C56 1.403(12) . ?
C55 H55 0.9300 . ?
C56 C57 1.369(14) . ?
C56 H56 0.9300 . ?
C57 C58 1.394(15) . ?
C57 H57 0.9300 . ?
C58 C59 1.382(12) . ?
C58 H58 0.9300 . ?
C59 H59 0.9300 . ?
C60 CL2 1.705(11) . ?
C60 CL1 1.728(12) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
N1 ZN1 2.163(5) . ?
N2 ZN1 2.089(5) . ?
N3 ZN1 2.087(5) . ?
N4 ZN1 2.094(5) . ?
N5 ZN1 2.092(6) . ?
O1 SN1 2.528(5) . ?
O2 SN1 2.124(5) . ?

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 C1 C2 117.3(7) . . ?
C6 C1 SN1 126.4(5) . . ?
C2 C1 SN1 116.2(5) . . ?
C3 C2 C1 121.6(7) . . ?
C3 C2 C7 120.2(7) . . ?
C1 C2 C7 118.2(7) . . ?
C4 C3 C2 120.5(8) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.0(8) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C6 122.5(8) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C1 C6 C5 119.9(7) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C2 123.6(7) . . ?
O1 C7 H7 118.2 . . ?
C2 C7 H7 118.2 . . ?
SN1 C8 H8A 109.5 . . ?
SN1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
SN1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
SN1 C9 H9A 109.5 . . ?
SN1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
SN1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 O2 123.8(6) . . ?
O3 C10 C11 122.7(6) . . ?
O2 C10 C11 113.5(6) . . ?
C12 C11 C15 118.2(6) . . ?
C12 C11 C10 118.9(6) . . ?
C15 C11 C10 122.7(6) . . ?
C11 C12 C13 118.0(7) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
N1 C13 C12 124.8(7) . . ?
N1 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?
N1 C14 C15 121.7(7) . . ?
N1 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C11 C15 C14 120.1(7) . . ?
C11 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
N2 C16 C35 125.9(6) . . ?
N2 C16 C17 108.8(6) . . ?
C35 C16 C17 125.2(6) . . ?
C18 C17 C16 107.4(6) . . ?
C18 C17 H17 126.3 . . ?
C16 C17 H17 126.3 . . ?
C17 C18 C19 107.7(6) . . ?
C17 C18 H18 126.2 . . ?
C19 C18 H18 126.2 . . ?
N2 C19 C20 126.1(6) . . ?
N2 C19 C18 109.0(5) . . ?
C20 C19 C18 124.8(6) . . ?
C21 C20 C19 125.9(6) . . ?
C21 C20 C36 116.3(6) . . ?
C19 C20 C36 117.8(6) . . ?
N3 C21 C20 124.6(6) . . ?
N3 C21 C22 109.7(6) . . ?
C20 C21 C22 125.6(6) . . ?
C23 C22 C21 107.9(6) . . ?
C23 C22 H22 126.0 . . ?
C21 C22 H22 126.0 . . ?
C22 C23 C24 106.6(6) . . ?
C22 C23 H23 126.7 . . ?
C24 C23 H23 126.7 . . ?
N3 C24 C25 125.6(6) . . ?
N3 C24 C23 109.7(6) . . ?
C25 C24 C23 124.7(6) . . ?
C26 C25 C24 125.0(6) . . ?
C26 C25 C42 119.4(6) . . ?
C24 C25 C42 115.6(6) . . ?
N4 C26 C25 126.7(6) . . ?
N4 C26 C27 108.2(6) . . ?
C25 C26 C27 125.1(7) . . ?
C28 C27 C26 107.8(6) . . ?
C28 C27 H27 126.1 . . ?
C26 C27 H27 126.1 . . ?
C27 C28 C29 107.6(6) . . ?
C27 C28 H28 126.2 . . ?
C29 C28 H28 126.2 . . ?
N4 C29 C30 125.7(6) . . ?
N4 C29 C28 109.0(6) . . ?
C30 C29 C28 125.4(6) . . ?
C31 C30 C29 125.3(6) . . ?
C31 C30 C48 117.2(6) . . ?
C29 C30 C48 117.4(6) . . ?
N5 C31 C30 125.1(6) . . ?
N5 C31 C32 109.3(6) . . ?
C30 C31 C32 125.6(6) . . ?
C33 C32 C31 108.4(6) . . ?
C33 C32 H32 125.8 . . ?
C31 C32 H32 125.8 . . ?
C32 C33 C34 106.8(7) . . ?
C32 C33 H33 126.6 . . ?
C34 C33 H33 126.6 . . ?
N5 C34 C35 124.7(6) . . ?
N5 C34 C33 109.7(6) . . ?
C35 C34 C33 125.6(6) . . ?
C16 C35 C34 125.8(6) . . ?
C16 C35 C54 117.2(6) . . ?
C34 C35 C54 116.9(6) . . ?
C41 C36 C37 118.3(7) . . ?
C41 C36 C20 119.9(6) . . ?
C37 C36 C20 121.7(6) . . ?
C38 C37 C36 120.1(7) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C39 C38 C37 121.0(8) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C40 C39 C38 118.6(7) . . ?
C40 C39 H39 120.7 . . ?
C38 C39 H39 120.7 . . ?
C39 C40 C41 121.6(7) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C40 C41 C36 120.5(8) . . ?
C40 C41 H41 119.8 . . ?
C36 C41 H41 119.8 . . ?
C43 C42 C47 118.2(8) . . ?
C43 C42 C25 121.1(8) . . ?
C47 C42 C25 120.5(7) . . ?
C42 C43 C44 119.1(9) . . ?
C42 C43 H43 120.5 . . ?
C44 C43 H43 120.5 . . ?
C45 C44 C43 120.3(9) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C46 C45 C44 121.0(9) . . ?
C46 C45 H45 119.5 . . ?
C44 C45 H45 119.5 . . ?
C45 C46 C47 119.2(10) . . ?
C45 C46 H46 120.4 . . ?
C47 C46 H46 120.4 . . ?
C46 C47 C42 122.2(8) . . ?
C46 C47 H47 118.9 . . ?
C42 C47 H47 118.9 . . ?
C49 C48 C53 117.7(7) . . ?
C49 C48 C30 119.4(7) . . ?
C53 C48 C30 122.8(7) . . ?
C48 C49 C50 121.1(8) . . ?
C48 C49 H49 119.4 . . ?
C50 C49 H49 119.4 . . ?
C51 C50 C49 119.7(8) . . ?
C51 C50 H50 120.2 . . ?
C49 C50 H50 120.2 . . ?
C52 C51 C50 120.1(9) . . ?
C52 C51 H51 120.0 . . ?
C50 C51 H51 120.0 . . ?
C51 C52 C53 120.5(10) . . ?
C51 C52 H52 119.8 . . ?
C53 C52 H52 119.8 . . ?
C52 C53 C48 120.9(9) . . ?
C52 C53 H53 119.5 . . ?
C48 C53 H53 119.5 . . ?
C55 C54 C59 118.0(7) . . ?
C55 C54 C35 124.3(7) . . ?
C59 C54 C35 117.6(6) . . ?
C54 C55 C56 121.5(9) . . ?
C54 C55 H55 119.2 . . ?
C56 C55 H55 119.2 . . ?
C57 C56 C55 119.2(9) . . ?
C57 C56 H56 120.4 . . ?
C55 C56 H56 120.4 . . ?
C56 C57 C58 120.4(9) . . ?
C56 C57 H57 119.8 . . ?
C58 C57 H57 119.8 . . ?
C59 C58 C57 120.7(10) . . ?
C59 C58 H58 119.7 . . ?
C57 C58 H58 119.7 . . ?
C58 C59 C54 120.2(9) . . ?
C58 C59 H59 119.9 . . ?
C54 C59 H59 119.9 . . ?
CL2 C60 CL1 117.3(7) . . ?
CL2 C60 H60A 108.0 . . ?
CL1 C60 H60A 108.0 . . ?
CL2 C60 H60B 108.0 . . ?
CL1 C60 H60B 108.0 . . ?
H60A C60 H60B 107.2 . . ?
C14 N1 C13 117.2(6) . . ?
C14 N1 ZN1 119.4(5) . . ?
C13 N1 ZN1 122.6(5) . . ?
C19 N2 C16 107.1(5) . . ?
C19 N2 ZN1 125.6(4) . . ?
C16 N2 ZN1 127.1(4) . . ?
C21 N3 C24 106.0(5) . . ?
C21 N3 ZN1 126.5(4) . . ?
C24 N3 ZN1 126.5(4) . . ?
C29 N4 C26 107.5(5) . . ?
C29 N4 ZN1 126.1(4) . . ?
C26 N4 ZN1 125.6(4) . . ?
C31 N5 C34 105.8(5) . . ?
C31 N5 ZN1 126.3(5) . . ?
C34 N5 ZN1 127.1(4) . . ?
C7 O1 SN1 108.6(5) . . ?
C10 O2 SN1 116.4(4) . . ?
C9 SN1 O2 101.2(3) . . ?
C9 SN1 C8 121.6(4) . . ?
O2 SN1 C8 91.0(3) . . ?
C9 SN1 C1 119.1(3) . . ?
O2 SN1 C1 101.4(2) . . ?
C8 SN1 C1 113.6(3) . . ?
C9 SN1 O1 85.8(3) . . ?
O2 SN1 O1 172.6(2) . . ?
C8 SN1 O1 87.3(3) . . ?
C1 SN1 O1 72.8(2) . . ?
N3 ZN1 N2 89.2(2) . . ?
N3 ZN1 N5 160.4(2) . . ?
N2 ZN1 N5 87.8(2) . . ?
N3 ZN1 N4 88.1(2) . . ?
N2 ZN1 N4 160.3(2) . . ?
N5 ZN1 N4 88.2(2) . . ?
N3 ZN1 N1 101.5(2) . . ?
N2 ZN1 N1 102.2(2) . . ?
N5 ZN1 N1 98.1(2) . . ?
N4 ZN1 N1 97.4(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
C6 C1 C2 C3 -2.4(11) . . . . ?
SN1 C1 C2 C3 175.2(6) . . . . ?
C6 C1 C2 C7 176.7(7) . . . . ?
SN1 C1 C2 C7 -5.6(9) . . . . ?
C1 C2 C3 C4 -0.1(12) . . . . ?
C7 C2 C3 C4 -179.2(8) . . . . ?
C2 C3 C4 C5 2.6(13) . . . . ?
C3 C4 C5 C6 -2.7(13) . . . . ?
C2 C1 C6 C5 2.3(11) . . . . ?
SN1 C1 C6 C5 -175.1(5) . . . . ?
C4 C5 C6 C1 0.2(12) . . . . ?
C3 C2 C7 O1 177.7(9) . . . . ?
C1 C2 C7 O1 -1.4(14) . . . . ?
O3 C10 C11 C12 10.7(10) . . . . ?
O2 C10 C11 C12 -168.1(6) . . . . ?
O3 C10 C11 C15 -174.2(7) . . . . ?
O2 C10 C11 C15 7.0(10) . . . . ?
C15 C11 C12 C13 -0.6(11) . . . . ?
C10 C11 C12 C13 174.7(7) . . . . ?
C11 C12 C13 N1 0.5(12) . . . . ?
C12 C11 C15 C14 0.4(11) . . . . ?
C10 C11 C15 C14 -174.7(7) . . . . ?
N1 C14 C15 C11 0.0(11) . . . . ?
N2 C16 C17 C18 -0.4(7) . . . . ?
C35 C16 C17 C18 175.8(6) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
C17 C18 C19 N2 0.4(7) . . . . ?
C17 C18 C19 C20 -177.6(6) . . . . ?
N2 C19 C20 C21 -0.9(10) . . . . ?
C18 C19 C20 C21 176.8(6) . . . . ?
N2 C19 C20 C36 -179.6(6) . . . . ?
C18 C19 C20 C36 -2.0(9) . . . . ?
C19 C20 C21 N3 -3.3(10) . . . . ?
C36 C20 C21 N3 175.5(6) . . . . ?
C19 C20 C21 C22 179.4(6) . . . . ?
C36 C20 C21 C22 -1.8(9) . . . . ?
N3 C21 C22 C23 -0.8(8) . . . . ?
C20 C21 C22 C23 176.9(6) . . . . ?
C21 C22 C23 C24 0.3(8) . . . . ?
C22 C23 C24 N3 0.3(8) . . . . ?
C22 C23 C24 C25 -177.2(7) . . . . ?
N3 C24 C25 C26 1.6(11) . . . . ?
C23 C24 C25 C26 178.7(7) . . . . ?
N3 C24 C25 C42 -177.4(7) . . . . ?
C23 C24 C25 C42 -0.3(10) . . . . ?
C24 C25 C26 N4 1.6(11) . . . . ?
C42 C25 C26 N4 -179.4(6) . . . . ?
C24 C25 C26 C27 179.5(7) . . . . ?
C42 C25 C26 C27 -1.5(10) . . . . ?
N4 C26 C27 C28 -0.2(8) . . . . ?
C25 C26 C27 C28 -178.4(7) . . . . ?
C26 C27 C28 C29 0.5(8) . . . . ?
C27 C28 C29 N4 -0.6(8) . . . . ?
C27 C28 C29 C30 179.1(6) . . . . ?
N4 C29 C30 C31 -5.5(10) . . . . ?
C28 C29 C30 C31 174.8(6) . . . . ?
N4 C29 C30 C48 175.9(6) . . . . ?
C28 C29 C30 C48 -3.8(10) . . . . ?
C29 C30 C31 N5 4.3(10) . . . . ?
C48 C30 C31 N5 -177.1(6) . . . . ?
C29 C30 C31 C32 -174.5(6) . . . . ?
C48 C30 C31 C32 4.1(10) . . . . ?
N5 C31 C32 C33 -1.0(8) . . . . ?
C30 C31 C32 C33 178.0(6) . . . . ?
C31 C32 C33 C34 1.0(8) . . . . ?
C32 C33 C34 N5 -0.7(8) . . . . ?
C32 C33 C34 C35 179.6(6) . . . . ?
N2 C16 C35 C34 0.1(10) . . . . ?
C17 C16 C35 C34 -175.5(6) . . . . ?
N2 C16 C35 C54 178.6(6) . . . . ?
C17 C16 C35 C54 3.0(9) . . . . ?
N5 C34 C35 C16 1.0(10) . . . . ?
C33 C34 C35 C16 -179.4(6) . . . . ?
N5 C34 C35 C54 -177.5(6) . . . . ?
C33 C34 C35 C54 2.1(10) . . . . ?
C21 C20 C36 C41 -82.4(8) . . . . ?
C19 C20 C36 C41 96.5(8) . . . . ?
C21 C20 C36 C37 95.2(8) . . . . ?
C19 C20 C36 C37 -85.9(8) . . . . ?
C41 C36 C37 C38 0.6(12) . . . . ?
C20 C36 C37 C38 -177.0(7) . . . . ?
C36 C37 C38 C39 -0.2(13) . . . . ?
C37 C38 C39 C40 0.0(13) . . . . ?
C38 C39 C40 C41 -0.3(13) . . . . ?
C39 C40 C41 C36 0.8(13) . . . . ?
C37 C36 C41 C40 -0.9(12) . . . . ?
C20 C36 C41 C40 176.8(7) . . . . ?
C26 C25 C42 C43 98.4(9) . . . . ?
C24 C25 C42 C43 -82.5(9) . . . . ?
C26 C25 C42 C47 -86.3(9) . . . . ?
C24 C25 C42 C47 92.8(9) . . . . ?
C47 C42 C43 C44 0.4(13) . . . . ?
C25 C42 C43 C44 175.8(8) . . . . ?
C42 C43 C44 C45 -0.3(15) . . . . ?
C43 C44 C45 C46 0.7(16) . . . . ?
C44 C45 C46 C47 -1.1(15) . . . . ?
C45 C46 C47 C42 1.2(14) . . . . ?
C43 C42 C47 C46 -0.8(13) . . . . ?
C25 C42 C47 C46 -176.3(8) . . . . ?
C31 C30 C48 C49 102.8(8) . . . . ?
C29 C30 C48 C49 -78.5(9) . . . . ?
C31 C30 C48 C53 -75.1(10) . . . . ?
C29 C30 C48 C53 103.7(10) . . . . ?
C53 C48 C49 C50 -2.2(14) . . . . ?
C30 C48 C49 C50 179.9(8) . . . . ?
C48 C49 C50 C51 2.0(15) . . . . ?
C49 C50 C51 C52 -0.8(17) . . . . ?
C50 C51 C52 C53 -0.2(19) . . . . ?
C51 C52 C53 C48 0.0(19) . . . . ?
C49 C48 C53 C52 1.1(16) . . . . ?
C30 C48 C53 C52 179.0(10) . . . . ?
C16 C35 C54 C55 94.1(8) . . . . ?
C34 C35 C54 C55 -87.3(9) . . . . ?
C16 C35 C54 C59 -82.0(8) . . . . ?
C34 C35 C54 C59 96.6(8) . . . . ?
C59 C54 C55 C56 1.2(12) . . . . ?
C35 C54 C55 C56 -174.9(7) . . . . ?
C54 C55 C56 C57 -0.4(13) . . . . ?
C55 C56 C57 C58 -1.4(14) . . . . ?
C56 C57 C58 C59 2.5(15) . . . . ?
C57 C58 C59 C54 -1.7(14) . . . . ?
C55 C54 C59 C58 -0.1(12) . . . . ?
C35 C54 C59 C58 176.2(8) . . . . ?
C15 C14 N1 C13 -0.1(10) . . . . ?
C15 C14 N1 ZN1 170.0(6) . . . . ?
C12 C13 N1 C14 -0.2(11) . . . . ?
C12 C13 N1 ZN1 -169.9(6) . . . . ?
C20 C19 N2 C16 177.3(6) . . . . ?
C18 C19 N2 C16 -0.6(7) . . . . ?
C20 C19 N2 ZN1 -6.5(9) . . . . ?
C18 C19 N2 ZN1 175.6(4) . . . . ?
C35 C16 N2 C19 -175.5(6) . . . . ?
C17 C16 N2 C19 0.7(7) . . . . ?
C35 C16 N2 ZN1 8.3(9) . . . . ?
C17 C16 N2 ZN1 -175.5(4) . . . . ?
C20 C21 N3 C24 -176.7(6) . . . . ?
C22 C21 N3 C24 1.0(7) . . . . ?
C20 C21 N3 ZN1 14.3(9) . . . . ?
C22 C21 N3 ZN1 -168.0(4) . . . . ?
C25 C24 N3 C21 176.7(6) . . . . ?
C23 C24 N3 C21 -0.8(7) . . . . ?
C25 C24 N3 ZN1 -14.3(10) . . . . ?
C23 C24 N3 ZN1 168.2(5) . . . . ?
C30 C29 N4 C26 -179.3(6) . . . . ?
C28 C29 N4 C26 0.5(7) . . . . ?
C30 C29 N4 ZN1 -9.4(9) . . . . ?
C28 C29 N4 ZN1 170.3(4) . . . . ?
C25 C26 N4 C29 178.0(6) . . . . ?
C27 C26 N4 C29 -0.2(7) . . . . ?
C25 C26 N4 ZN1 8.1(9) . . . . ?
C27 C26 N4 ZN1 -170.1(4) . . . . ?
C30 C31 N5 C34 -178.5(6) . . . . ?
C32 C31 N5 C34 0.5(7) . . . . ?
C30 C31 N5 ZN1 11.7(9) . . . . ?
C32 C31 N5 ZN1 -169.4(4) . . . . ?
C35 C34 N5 C31 179.8(6) . . . . ?
C33 C34 N5 C31 0.1(7) . . . . ?
C35 C34 N5 ZN1 -10.4(9) . . . . ?
C33 C34 N5 ZN1 169.9(4) . . . . ?
C2 C7 O1 SN1 6.3(11) . . . . ?
O3 C10 O2 SN1 -1.6(9) . . . . ?
C11 C10 O2 SN1 177.1(4) . . . . ?

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.106

