# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

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

data_mash58m
_database_code_depnum_ccdc_archive 'CCDC 1848467'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 Cl N O Sn'
_chemical_formula_sum            'C11 H14 Cl N O Sn'
_chemical_formula_weight         330.39

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_hall  '-P 2ybc'

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

_cell_length_a                   8.9661(19)
_cell_length_b                   14.357(3)
_cell_length_c                   10.110(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.154(4)
_cell_angle_gamma                90.00
_cell_volume                     1229.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2986
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.10

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.0
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_T_max  0.568
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4538
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1700
_reflns_number_gt                1317
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0703P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1700
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.26156(6) 1.00452(3) 0.51371(5) 0.0323(2) Uani 1 1 d . . .
C11 C 0.1956(9) 0.9537(5) 0.1316(7) 0.0411(17) Uani 1 1 d . . .
H11A H 0.2115 0.9596 0.0426 0.062 Uiso 1 1 calc R . .
H11B H 0.2903 0.9715 0.2048 0.062 Uiso 1 1 calc R . .
H11C H 0.1104 0.9935 0.1338 0.062 Uiso 1 1 calc R . .
N1 N 0.2527(6) 0.8678(3) 0.4171(5) 0.0302(12) Uani 1 1 d . . .
O1 O 0.4712(5) 0.9345(3) 0.6340(5) 0.0379(11) Uani 1 1 d . . .
C1 C 0.3692(7) 0.8082(4) 0.4797(6) 0.0284(14) Uani 1 1 d . . .
Cl1 Cl 0.1208(2) 0.94454(11) 0.67652(17) 0.0407(5) Uani 1 1 d . . .
C2 C 0.3796(8) 0.7180(4) 0.4263(7) 0.0351(16) Uani 1 1 d . . .
H2 H 0.3045 0.7061 0.3395 0.042 Uiso 1 1 calc R . .
C3 C 0.4787(8) 0.6466(5) 0.4787(7) 0.0386(19) Uani 1 1 d . . .
H3 H 0.4578 0.5934 0.4231 0.046 Uiso 1 1 calc R . .
C4 C 0.6086(9) 0.6383(5) 0.6029(7) 0.0444(19) Uani 1 1 d . . .
H4 H 0.6601 0.5811 0.6210 0.053 Uiso 1 1 calc R . .
C5 C 0.6645(9) 0.7078(5) 0.6986(8) 0.0470(19) Uani 1 1 d . . .
H5 H 0.7492 0.6912 0.7768 0.056 Uiso 1 1 calc R . .
C6 C 0.6143(8) 0.7996(4) 0.6972(7) 0.0381(16) Uani 1 1 d . . .
H6 H 0.6767 0.8356 0.7711 0.046 Uiso 1 1 calc R . .
C7 C 0.4887(8) 0.8464(4) 0.6059(6) 0.0332(15) Uani 1 1 d . . .
C8 C 0.1232(8) 0.8416(4) 0.2920(6) 0.0312(14) Uani 1 1 d . . .
H8A H 0.0316 0.8788 0.2881 0.037 Uiso 1 1 calc R . .
H8B H 0.0965 0.7769 0.3011 0.037 Uiso 1 1 calc R . .
C9 C 0.1554(8) 0.8530(4) 0.1532(6) 0.0324(15) Uani 1 1 d . . .
H9 H 0.2454 0.8136 0.1553 0.039 Uiso 1 1 calc R . .
C10 C 0.0107(9) 0.8202(6) 0.0341(7) 0.046(2) Uani 1 1 d . . .
H10A H -0.0793 0.8566 0.0334 0.070 Uiso 1 1 calc R . .
H10B H -0.0089 0.7558 0.0476 0.070 Uiso 1 1 calc R . .
H10C H 0.0294 0.8276 -0.0535 0.070 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn1 0.0321(4) 0.0242(3) 0.0337(3) -0.00239(16) 0.0014(3) 0.00001(16)
C11 0.044(5) 0.035(4) 0.039(4) 0.003(3) 0.006(3) -0.004(3)
N1 0.025(3) 0.032(3) 0.024(3) -0.002(2) -0.005(2) -0.003(2)
O1 0.029(3) 0.031(2) 0.041(2) -0.008(2) -0.006(2) 0.0026(19)
C1 0.032(4) 0.028(3) 0.022(3) 0.004(2) 0.004(3) 0.000(3)
Cl1 0.0417(11) 0.0415(9) 0.0333(8) 0.0033(7) 0.0048(8) 0.0065(8)
C2 0.042(4) 0.022(3) 0.034(3) 0.000(3) 0.003(3) -0.002(3)
C3 0.048(5) 0.030(4) 0.039(4) 0.001(3) 0.018(4) 0.004(3)
C4 0.049(5) 0.026(3) 0.049(4) 0.007(3) 0.005(4) 0.012(3)
C5 0.036(4) 0.051(4) 0.043(4) 0.012(3) -0.002(4) 0.010(4)
C6 0.031(4) 0.037(4) 0.036(4) -0.001(3) -0.004(3) 0.003(3)
C7 0.033(4) 0.031(4) 0.031(3) 0.000(3) 0.005(3) -0.001(3)
C8 0.029(4) 0.027(3) 0.029(3) -0.005(2) -0.002(3) 0.002(3)
C9 0.032(4) 0.031(3) 0.026(3) 0.004(3) -0.001(3) 0.009(3)
C10 0.053(5) 0.045(4) 0.028(3) -0.004(3) -0.005(3) 0.002(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 O1 2.127(4) . ?
Sn1 N1 2.183(5) . ?
Sn1 Cl1 2.5314(19) . ?
C11 C9 1.523(9) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 C1 1.337(8) . ?
N1 C8 1.458(7) . ?
O1 C7 1.317(7) . ?
C1 C2 1.418(8) . ?
C1 C7 1.476(8) . ?
C2 C3 1.347(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(9) . ?
C6 H6 0.9300 . ?
C8 C9 1.532(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.526(9) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sn1 N1 74.12(17) . . ?
O1 Sn1 Cl1 90.19(14) . . ?
N1 Sn1 Cl1 91.86(14) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C8 121.5(5) . . ?
C1 N1 Sn1 117.1(4) . . ?
C8 N1 Sn1 121.5(4) . . ?
C7 O1 Sn1 118.4(4) . . ?
N1 C1 C2 122.8(6) . . ?
N1 C1 C7 113.9(5) . . ?
C2 C1 C7 123.2(6) . . ?
C3 C2 C1 131.6(7) . . ?
C3 C2 H2 114.2 . . ?
C1 C2 H2 114.2 . . ?
C2 C3 C4 131.3(7) . . ?
C2 C3 H3 114.3 . . ?
C4 C3 H3 114.3 . . ?
C5 C4 C3 125.0(7) . . ?
C5 C4 H4 117.5 . . ?
C3 C4 H4 117.5 . . ?
C4 C5 C6 130.0(7) . . ?
C4 C5 H5 115.0 . . ?
C6 C5 H5 115.0 . . ?
C7 C6 C5 131.4(6) . . ?
C7 C6 H6 114.3 . . ?
C5 C6 H6 114.3 . . ?
O1 C7 C6 117.0(6) . . ?
O1 C7 C1 116.0(5) . . ?
C6 C7 C1 127.0(6) . . ?
N1 C8 C9 115.5(6) . . ?
N1 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
N1 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C11 C9 C10 111.1(5) . . ?
C11 C9 C8 110.9(5) . . ?
C10 C9 C8 108.8(6) . . ?
C11 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
O1 Sn1 N1 C1 3.6(4) . . . . ?
Cl1 Sn1 N1 C1 -86.0(4) . . . . ?
O1 Sn1 N1 C8 -178.1(5) . . . . ?
Cl1 Sn1 N1 C8 92.3(5) . . . . ?
N1 Sn1 O1 C7 -6.3(5) . . . . ?
Cl1 Sn1 O1 C7 85.6(5) . . . . ?
C8 N1 C1 C2 3.1(9) . . . . ?
Sn1 N1 C1 C2 -178.6(5) . . . . ?
C8 N1 C1 C7 -179.2(6) . . . . ?
Sn1 N1 C1 C7 -0.9(7) . . . . ?
N1 C1 C2 C3 -174.1(7) . . . . ?
C7 C1 C2 C3 8.4(11) . . . . ?
C1 C2 C3 C4 -2.0(14) . . . . ?
C2 C3 C4 C5 -2.0(14) . . . . ?
C3 C4 C5 C6 -1.8(14) . . . . ?
C4 C5 C6 C7 5.0(15) . . . . ?
Sn1 O1 C7 C6 -171.3(5) . . . . ?
Sn1 O1 C7 C1 8.0(7) . . . . ?
C5 C6 C7 O1 179.4(8) . . . . ?
C5 C6 C7 C1 0.2(13) . . . . ?
N1 C1 C7 O1 -4.5(8) . . . . ?
C2 C1 C7 O1 173.1(6) . . . . ?
N1 C1 C7 C6 174.7(6) . . . . ?
C2 C1 C7 C6 -7.6(10) . . . . ?
C1 N1 C8 C9 -84.4(7) . . . . ?
Sn1 N1 C8 C9 97.4(6) . . . . ?
N1 C8 C9 C11 -59.1(7) . . . . ?
N1 C8 C9 C10 178.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.660
_refine_diff_density_min         -1.071
_refine_diff_density_rms         0.151
####################################################################### 
# 
# 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_mssh12m
_database_code_depnum_ccdc_archive 'CCDC 1848468'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 F3 N O4 S Sn'
_chemical_formula_sum            'C12 H14 F3 N O4 S Sn'
_chemical_formula_weight         444.01

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

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

_cell_length_a                   5.9965(18)
_cell_length_b                   9.897(3)
_cell_length_c                   13.761(4)
_cell_angle_alpha                81.041(5)
_cell_angle_beta                 79.279(6)
_cell_angle_gamma                72.687(5)
_cell_volume                     761.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1618
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.12

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.351
_exptl_crystal_size_min          0.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436.0
_exptl_absorpt_coefficient_mu    1.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3811
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0857
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2605
_reflns_number_gt                2398
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1278P)²+16.3229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2690
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.2326
_refine_ls_wR_factor_gt          0.2228
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.022

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn -0.25420(13) 0.43635(8) 0.09981(6) 0.0192(3) Uani 1 1 d . . .
S1 S 0.0870(6) 0.5755(3) 0.2102(2) 0.0206(7) Uani 1 1 d . . .
O1 O 0.1028(15) 0.3655(9) 0.0394(6) 0.0210(18) Uani 1 1 d . . .
O3 O 0.2572(15) 0.4399(9) 0.2301(7) 0.026(2) Uani 1 1 d . . .
N1 N -0.0996(19) 0.2377(12) 0.1920(8) 0.024(2) Uani 1 1 d . . .
O4 O 0.1659(17) 0.6780(9) 0.1372(7) 0.027(2) Uani 1 1 d . . .
F3 F -0.1289(18) 0.7802(9) 0.3226(6) 0.046(2) Uani 1 1 d . . .
F2 F 0.2259(19) 0.6737(10) 0.3456(7) 0.051(2) Uani 1 1 d . . .
F1 F -0.043(2) 0.5701(9) 0.4022(6) 0.049(3) Uani 1 1 d . . .
O2 O -0.1490(16) 0.5642(10) 0.2015(7) 0.026(2) Uani 1 1 d . . .
C9 C -0.251(3) 0.242(2) 0.3732(12) 0.044(4) Uani 1 1 d . . .
H9 H -0.3026 0.3455 0.3591 0.053 Uiso 1 1 calc R . .
C7 C 0.121(2) 0.1740(13) 0.1637(9) 0.020(3) Uani 1 1 d . . .
C8 C -0.249(2) 0.1837(13) 0.2776(10) 0.024(3) Uani 1 1 d . . .
H8A H -0.1932 0.0807 0.2867 0.029 Uiso 1 1 calc R . .
H8B H -0.4098 0.2092 0.2631 0.029 Uiso 1 1 calc R . .
C1 C 0.241(2) 0.2448(12) 0.0786(9) 0.020(3) Uani 1 1 d . . .
C4 C 0.655(3) -0.0318(14) 0.1232(10) 0.027(3) Uani 1 1 d . . .
H4 H 0.7951 -0.1043 0.1249 0.033 Uiso 1 1 calc R . .
C5 C 0.458(2) -0.0511(14) 0.1917(11) 0.029(3) Uani 1 1 d . . .
H5 H 0.4862 -0.1378 0.2313 0.034 Uiso 1 1 calc R . .
C6 C 0.235(2) 0.0348(13) 0.2100(10) 0.024(3) Uani 1 1 d . . .
H6 H 0.1378 -0.0022 0.2614 0.029 Uiso 1 1 calc R . .
C2 C 0.470(2) 0.2030(14) 0.0330(10) 0.025(3) Uani 1 1 d . . .
H2 H 0.5083 0.2644 -0.0218 0.030 Uiso 1 1 calc R . .
C12 C 0.029(3) 0.6565(15) 0.3274(11) 0.036(3) Uani 1 1 d . . .
C3 C 0.660(2) 0.0829(13) 0.0545(10) 0.025(3) Uani 1 1 d . . .
H3 H 0.8059 0.0822 0.0170 0.030 Uiso 1 1 calc R . .
C11 C -0.024(5) 0.210(3) 0.4052(17) 0.080(7) Uani 1 1 d . . .
H11A H -0.0333 0.2700 0.4552 0.119 Uiso 1 1 calc R . .
H11B H 0.0911 0.2270 0.3494 0.119 Uiso 1 1 calc R . .
H11C H 0.0230 0.1121 0.4322 0.119 Uiso 1 1 calc R . .
C10 C -0.434(6) 0.204(4) 0.4491(18) 0.146(13) Uani 1 1 d . . .
H10A H -0.3793 0.1064 0.4757 0.219 Uiso 1 1 calc R . .
H10B H -0.5737 0.2168 0.4198 0.219 Uiso 1 1 calc R . .
H10C H -0.4711 0.2642 0.5016 0.219 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn1 0.0137(5) 0.0126(5) 0.0322(6) 0.0080(3) -0.0090(3) -0.0069(3)
S1 0.0273(16) 0.0110(14) 0.0199(15) -0.0005(11) -0.0010(12) -0.0020(12)
O1 0.022(4) 0.015(4) 0.026(5) 0.002(3) -0.005(3) -0.006(3)
O3 0.023(5) 0.021(5) 0.034(5) 0.004(4) -0.009(4) -0.007(4)
N1 0.022(6) 0.029(6) 0.028(6) 0.005(4) -0.008(4) -0.017(5)
O4 0.034(5) 0.019(4) 0.027(5) 0.004(4) 0.001(4) -0.012(4)
F3 0.073(7) 0.026(4) 0.032(5) -0.009(4) -0.002(4) -0.003(4)
F2 0.069(7) 0.041(5) 0.054(6) -0.013(4) -0.028(5) -0.018(5)
F1 0.093(8) 0.029(5) 0.021(4) 0.002(3) -0.001(4) -0.020(5)
O2 0.023(5) 0.024(5) 0.029(5) 0.000(4) -0.003(4) -0.007(4)
C9 0.034(8) 0.066(11) 0.050(10) -0.032(8) 0.016(7) -0.037(8)
C7 0.021(6) 0.018(6) 0.029(7) 0.000(5) -0.009(5) -0.015(5)
C8 0.027(7) 0.012(6) 0.034(7) -0.002(5) -0.005(5) -0.006(5)
C1 0.026(6) 0.012(6) 0.024(6) 0.002(5) -0.002(5) -0.011(5)
C4 0.036(8) 0.017(6) 0.034(7) -0.009(5) -0.007(6) -0.010(6)
C5 0.032(7) 0.021(6) 0.036(8) 0.003(5) -0.015(6) -0.010(6)
C6 0.030(7) 0.012(6) 0.031(7) 0.004(5) -0.011(5) -0.008(5)
C2 0.034(7) 0.024(7) 0.023(7) -0.002(5) -0.006(5) -0.014(6)
C12 0.051(9) 0.020(7) 0.035(8) -0.007(6) -0.005(7) -0.006(7)
C3 0.031(7) 0.016(6) 0.030(7) -0.008(5) -0.005(6) -0.004(5)
C11 0.11(2) 0.084(17) 0.057(13) -0.004(12) -0.002(13) -0.060(16)
C10 0.17(3) 0.29(4) 0.053(15) -0.065(18) 0.046(15) -0.19(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 O1 2.096(8) . ?
Sn1 N1 2.216(11) . ?
Sn1 O2 2.304(9) . ?
S1 O4 1.433(9) . ?
S1 O3 1.446(9) . ?
S1 O2 1.481(10) . ?
S1 C12 1.841(15) . ?
O1 C1 1.334(15) . ?
N1 C7 1.297(17) . ?
N1 C8 1.475(16) . ?
F3 C12 1.306(17) . ?
F2 C12 1.316(19) . ?
F1 C12 1.327(17) . ?
C9 C11 1.44(3) . ?
C9 C10 1.46(3) . ?
C9 C8 1.51(2) . ?
C7 C6 1.449(17) . ?
C7 C1 1.453(17) . ?
C1 C2 1.372(19) . ?
C4 C3 1.364(19) . ?
C4 C5 1.41(2) . ?
C5 C6 1.36(2) . ?
C2 C3 1.414(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Sn1 N1 73.2(4) . . ?
O1 Sn1 O2 88.6(3) . . ?
N1 Sn1 O2 89.3(4) . . ?
O4 S1 O3 117.2(6) . . ?
O4 S1 O2 113.7(6) . . ?
O3 S1 O2 114.0(5) . . ?
O4 S1 C12 103.8(6) . . ?
O3 S1 C12 103.5(6) . . ?
O2 S1 C12 102.2(6) . . ?
C1 O1 Sn1 120.2(7) . . ?
C7 N1 C8 124.3(11) . . ?
C7 N1 Sn1 116.1(8) . . ?
C8 N1 Sn1 119.6(8) . . ?
S1 O2 Sn1 129.9(5) . . ?
C11 C9 C10 115(2) . . ?
C11 C9 C8 115.3(15) . . ?
C10 C9 C8 109.2(14) . . ?
N1 C7 C6 121.5(11) . . ?
N1 C7 C1 116.4(11) . . ?
C6 C7 C1 122.0(11) . . ?
N1 C8 C9 113.0(11) . . ?
O1 C1 C2 116.8(11) . . ?
O1 C1 C7 114.0(11) . . ?
C2 C1 C7 129.1(12) . . ?
C3 C4 C5 126.2(13) . . ?
C6 C5 C4 131.3(13) . . ?
C5 C6 C7 131.4(13) . . ?
C1 C2 C3 131.4(12) . . ?
F3 C12 F1 110.1(13) . . ?
F3 C12 F2 108.8(12) . . ?
F1 C12 F2 107.4(13) . . ?
F3 C12 S1 111.3(11) . . ?
F1 C12 S1 109.8(9) . . ?
F2 C12 S1 109.4(10) . . ?
C4 C3 C2 128.3(13) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         3.088
_refine_diff_density_min         -1.704
_refine_diff_density_rms         0.331
