# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_s4129ma
_database_code_depnum_ccdc_archive 'CCDC 1053639'
_audit_update_record             
;
2015-03-11 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H38 N2 S4 Sn'
_chemical_formula_weight         553.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn 0.0259 5.4591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   19.852(2)
_cell_length_b                   6.7979(6)
_cell_length_c                   19.7407(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.635(4)
_cell_angle_gamma                90.00
_cell_volume                     2618.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5780
_cell_measurement_theta_min      4.53
_cell_measurement_theta_max      72.16

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    10.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.32679
_exptl_absorpt_correction_T_max  0.5636
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8266
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.53
_diffrn_reflns_theta_max         72.15
_reflns_number_total             2532
_reflns_number_gt                2402
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0315P)²+2.5154P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2532
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0581
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.04446(10) 0.1383(3) 0.10989(9) 0.0173(4) Uani 1 1 d . . .
C2 C 0.08548(10) -0.1494(3) 0.05164(10) 0.0197(4) Uani 1 1 d . . .
H2A H 0.0640 -0.2010 0.0058 0.024 Uiso 1 1 calc R . .
H2B H 0.0677 -0.2258 0.0873 0.024 Uiso 1 1 calc R . .
C3 C 0.16312(11) -0.1721(3) 0.06174(11) 0.0250(4) Uani 1 1 d . . .
H3A H 0.1842 -0.1304 0.1090 0.030 Uiso 1 1 calc R . .
H3B H 0.1748 -0.3120 0.0563 0.030 Uiso 1 1 calc R . .
C4 C 0.19182(12) -0.0478(3) 0.00938(12) 0.0281(5) Uani 1 1 d . . .
H4A H 0.1762 -0.1022 -0.0374 0.034 Uiso 1 1 calc R . .
H4B H 0.2425 -0.0533 0.0197 0.034 Uiso 1 1 calc R . .
C5 C 0.16849(11) 0.1659(3) 0.01116(10) 0.0243(4) Uani 1 1 d . . .
H5A H 0.1903 0.2265 0.0554 0.029 Uiso 1 1 calc R . .
H5B H 0.1836 0.2399 -0.0266 0.029 Uiso 1 1 calc R . .
C6 C 0.09103(10) 0.1805(3) 0.00336(9) 0.0197(4) Uani 1 1 d . . .
H6A H 0.0775 0.3193 0.0079 0.024 Uiso 1 1 calc R . .
H6B H 0.0690 0.1332 -0.0429 0.024 Uiso 1 1 calc R . .
C7 C -0.10195(11) 0.3545(3) 0.20851(10) 0.0224(4) Uani 1 1 d . . .
H7A H -0.1148 0.3057 0.1606 0.027 Uiso 1 1 calc R . .
H7B H -0.1339 0.2949 0.2357 0.027 Uiso 1 1 calc R . .
C8 C -0.11130(11) 0.5770(3) 0.20818(10) 0.0233(4) Uani 1 1 d . . .
H8A H -0.0825 0.6370 0.1778 0.028 Uiso 1 1 calc R . .
H8B H -0.0955 0.6282 0.2554 0.028 Uiso 1 1 calc R . .
C9 C -0.18569(12) 0.6376(3) 0.18338(12) 0.0301(5) Uani 1 1 d . . .
H9A H -0.2146 0.5751 0.2132 0.036 Uiso 1 1 calc R . .
H9B H -0.2012 0.5886 0.1358 0.036 Uiso 1 1 calc R . .
C10 C -0.19572(15) 0.8602(4) 0.18432(14) 0.0397(6) Uani 1 1 d . . .
H10A H -0.1820 0.9091 0.2316 0.060 Uiso 1 1 calc R . .
H10B H -0.2441 0.8916 0.1674 0.060 Uiso 1 1 calc R . .
H10C H -0.1675 0.9229 0.1546 0.060 Uiso 1 1 calc R . .
N1 N 0.06800(8) 0.0604(2) 0.05681(8) 0.0169(3) Uani 1 1 d . . .
S1 S 0.02299(3) -0.02174(7) 0.17188(2) 0.01931(11) Uani 1 1 d . . .
S2 S 0.03344(3) 0.38406(7) 0.11902(2) 0.02337(12) Uani 1 1 d . . .
Sn1 Sn 0.0000 0.25556(2) 0.2500 0.01823(8) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0207(10) 0.0158(9) 0.0148(8) 0.0016(7) 0.0012(7) -0.0042(7)
C2 0.0239(11) 0.0146(9) 0.0217(9) -0.0002(7) 0.0070(7) -0.0005(7)
C3 0.0243(11) 0.0221(11) 0.0287(10) 0.0006(8) 0.0053(8) 0.0034(8)
C4 0.0231(11) 0.0285(11) 0.0354(11) -0.0011(9) 0.0122(9) -0.0008(8)
C5 0.0232(11) 0.0255(11) 0.0257(10) 0.0009(8) 0.0088(8) -0.0063(8)
C6 0.0242(11) 0.0190(10) 0.0162(8) 0.0030(7) 0.0050(7) -0.0045(8)
C7 0.0255(11) 0.0171(10) 0.0225(9) 0.0000(7) -0.0008(8) -0.0019(8)
C8 0.0258(11) 0.0176(10) 0.0243(9) 0.0017(7) -0.0010(8) -0.0007(8)
C9 0.0290(12) 0.0266(12) 0.0322(11) 0.0039(9) -0.0008(9) 0.0009(9)
C10 0.0425(15) 0.0303(13) 0.0414(13) -0.0006(10) -0.0057(11) 0.0106(11)
N1 0.0181(8) 0.0153(8) 0.0183(7) 0.0012(6) 0.0056(6) -0.0018(6)
S1 0.0315(3) 0.0132(2) 0.0141(2) 0.00149(15) 0.00644(17) -0.00204(17)
S2 0.0402(3) 0.0123(2) 0.0184(2) 0.00068(16) 0.00763(19) -0.00219(19)
Sn1 0.02663(12) 0.01376(11) 0.01369(11) 0.000 0.00209(7) 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.333(3) . ?
C1 S2 1.699(2) . ?
C1 S1 1.7480(19) . ?
C2 N1 1.476(2) . ?
C2 C3 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.520(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.472(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(3) . ?
C7 Sn1 2.147(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.524(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.527(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
S1 Sn1 2.5298(5) . ?
S2 Sn1 2.9194(5) . ?
Sn1 C7 2.147(2) 2 ?
Sn1 S1 2.5299(5) 2 ?
Sn1 S2 2.9194(5) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S2 123.02(14) . . ?
N1 C1 S1 117.97(14) . . ?
S2 C1 S1 119.01(11) . . ?
N1 C2 C3 109.48(16) . . ?
N1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 110.52(17) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 111.03(18) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 111.40(17) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C5 109.49(16) . . ?
N1 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 Sn1 114.72(13) . . ?
C8 C7 H7A 108.6 . . ?
Sn1 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
Sn1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 112.31(17) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 112.63(19) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
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 . . ?
C1 N1 C6 122.90(16) . . ?
C1 N1 C2 124.01(16) . . ?
C6 N1 C2 112.23(15) . . ?
C1 S1 Sn1 93.31(7) . . ?
C1 S2 Sn1 81.64(6) . . ?
C7 Sn1 C7 143.48(11) 2 . ?
C7 Sn1 S1 101.69(6) 2 . ?
C7 Sn1 S1 105.33(5) . . ?
C7 Sn1 S1 105.33(5) 2 2 ?
C7 Sn1 S1 101.69(6) . 2 ?
S1 Sn1 S1 83.66(2) . 2 ?
C7 Sn1 S2 85.46(6) 2 2 ?
C7 Sn1 S2 83.78(6) . 2 ?
S1 Sn1 S2 149.202(14) . 2 ?
S1 Sn1 S2 65.603(14) 2 2 ?
C7 Sn1 S2 83.78(6) 2 . ?
C7 Sn1 S2 85.46(6) . . ?
S1 Sn1 S2 65.603(14) . . ?
S1 Sn1 S2 149.202(14) 2 . ?
S2 Sn1 S2 145.18(2) 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
N1 C2 C3 C4 -56.8(2) . . . . ?
C2 C3 C4 C5 53.3(2) . . . . ?
C3 C4 C5 C6 -52.9(2) . . . . ?
C4 C5 C6 N1 55.5(2) . . . . ?
Sn1 C7 C8 C9 -175.59(14) . . . . ?
C7 C8 C9 C10 178.81(18) . . . . ?
S2 C1 N1 C6 4.2(3) . . . . ?
S1 C1 N1 C6 -176.78(14) . . . . ?
S2 C1 N1 C2 172.72(14) . . . . ?
S1 C1 N1 C2 -8.2(3) . . . . ?
C5 C6 N1 C1 109.2(2) . . . . ?
C5 C6 N1 C2 -60.6(2) . . . . ?
C3 C2 N1 C1 -108.1(2) . . . . ?
C3 C2 N1 C6 61.5(2) . . . . ?
N1 C1 S1 Sn1 174.01(15) . . . . ?
S2 C1 S1 Sn1 -6.91(11) . . . . ?
N1 C1 S2 Sn1 -174.93(17) . . . . ?
S1 C1 S2 Sn1 6.04(10) . . . . ?
C8 C7 Sn1 C7 -2.77(13) . . . 2 ?
C8 C7 Sn1 S1 -139.09(13) . . . . ?
C8 C7 Sn1 S1 134.37(14) . . . 2 ?
C8 C7 Sn1 S2 70.91(14) . . . 2 ?
C8 C7 Sn1 S2 -75.92(14) . . . . ?
C1 S1 Sn1 C7 -73.71(8) . . . 2 ?
C1 S1 Sn1 C7 81.47(9) . . . . ?
C1 S1 Sn1 S1 -178.11(7) . . . 2 ?
C1 S1 Sn1 S2 -174.61(6) . . . 2 ?
C1 S1 Sn1 S2 3.85(6) . . . . ?
C1 S2 Sn1 C7 101.85(9) . . . 2 ?
C1 S2 Sn1 C7 -113.10(8) . . . . ?
C1 S2 Sn1 S1 -4.00(7) . . . . ?
C1 S2 Sn1 S1 -7.82(7) . . . 2 ?
C1 S2 Sn1 S2 174.62(7) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.008
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.080
