# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_Sn(Sepy)2Me2
_database_code_depnum_ccdc_archive 'CCDC 880459'
#TrackingRef 'RS-09.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 N2 Se2 Sn'
_chemical_formula_weight         462.86

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'
Se Se -0.0929 2.2259 '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           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33

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

_cell_length_a                   29.088(6)
_cell_length_b                   9.630(2)
_cell_length_c                   11.0000(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3081.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8.2
_cell_measurement_theta_max      13.4

_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    6.365
_exptl_absorpt_correction_type   psi-scans
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.2511
_exptl_absorpt_correction_T_max  0.3625


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -5.20
_diffrn_reflns_number            5299
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.1623
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         27.44
_reflns_number_total             4231
_reflns_number_gt                1929
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep 3 for windows'
_computing_publication_material  'WinGX 1.70.01'



_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_number_reflns         4231
_refine_ls_number_parameters     215
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1769
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.967
_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 0.4002(7) 0.752(2) 0.344(2) 0.065(3) Uani 1 1 d . . .
C2 C 0.3803(6) 0.887(2) 0.3365(18) 0.065(3) Uani 1 1 d . . .
H2 H 0.3612 0.9107 0.2722 0.079 Uiso 1 1 calc R . .
C3 C 0.3905(6) 0.984(2) 0.4301(18) 0.065(3) Uani 1 1 d . . .
H3 H 0.3769 1.0710 0.4305 0.079 Uiso 1 1 calc R . .
C4 C 0.4193(6) 0.948(2) 0.516(2) 0.065(3) Uani 1 1 d . . .
H4 H 0.4283 1.0136 0.5729 0.079 Uiso 1 1 calc R . .
C5 C 0.4370(6) 0.813(2) 0.524(2) 0.065(3) Uani 1 1 d . . .
H5 H 0.4549 0.7889 0.5912 0.079 Uiso 1 1 calc R . .
N1 N 0.4283(6) 0.7159(17) 0.4356(15) 0.062(5) Uani 1 1 d . . .
C6 C 0.4890(7) 0.158(2) 0.311(2) 0.068(3) Uani 1 1 d . . .
C7 C 0.5041(8) 0.028(2) 0.2937(19) 0.068(3) Uani 1 1 d . . .
H7 H 0.4937 -0.0237 0.2280 0.082 Uiso 1 1 calc R . .
C8 C 0.5366(6) -0.029(2) 0.377(2) 0.068(3) Uani 1 1 d . . .
H8 H 0.5481 -0.1183 0.3682 0.082 Uiso 1 1 calc R . .
C9 C 0.5495(6) 0.053(2) 0.4693(19) 0.068(3) Uani 1 1 d . . .
H9 H 0.5720 0.0224 0.5230 0.082 Uiso 1 1 calc R . .
C10 C 0.5301(6) 0.181(2) 0.485(2) 0.068(3) Uani 1 1 d . . .
H10 H 0.5384 0.2332 0.5529 0.082 Uiso 1 1 calc R . .
N2 N 0.5002(5) 0.2315(17) 0.4087(15) 0.065(5) Uani 1 1 d . . .
C11 C 0.4111(6) 0.400(2) 0.5199(17) 0.071(6) Uani 1 1 d . . .
H11A H 0.4046 0.3024 0.5168 0.107 Uiso 1 1 calc R . .
H11B H 0.3829 0.4511 0.5257 0.107 Uiso 1 1 calc R . .
H11C H 0.4299 0.4195 0.5897 0.107 Uiso 1 1 calc R . .
C12 C 0.5125(6) 0.555(2) 0.336(2) 0.089(8) Uani 1 1 d . . .
H12A H 0.5236 0.5856 0.4143 0.134 Uiso 1 1 calc R . .
H12B H 0.5097 0.6340 0.2832 0.134 Uiso 1 1 calc R . .
H12C H 0.5336 0.4897 0.3023 0.134 Uiso 1 1 calc R . .
C23 C 0.2343(6) 0.268(2) -0.112(2) 0.078(7) Uani 1 1 d . . .
H23A H 0.2268 0.3227 -0.1824 0.117 Uiso 1 1 calc R . .
H23B H 0.2324 0.3245 -0.0407 0.117 Uiso 1 1 calc R . .
H23C H 0.2131 0.1918 -0.1057 0.117 Uiso 1 1 calc R . .
C24 C 0.3368(7) 0.128(2) -0.293(2) 0.092(8) Uani 1 1 d . . .
H24A H 0.3687 0.1121 -0.2771 0.138 Uiso 1 1 calc R . .
H24B H 0.3337 0.2002 -0.3530 0.138 Uiso 1 1 calc R . .
H24C H 0.3231 0.0441 -0.3239 0.138 Uiso 1 1 calc R . .
Se1 Se 0.38946(7) 0.6087(2) 0.2297(2) 0.0656(6) Uani 1 1 d . . .
Se2 Se 0.44421(7) 0.2474(2) 0.21052(18) 0.0667(7) Uani 1 1 d . . .
Se3 Se 0.31624(7) -0.0080(3) 0.0270(2) 0.0732(7) Uani 1 1 d . . .
Se4 Se 0.35972(8) 0.3497(3) -0.0173(2) 0.0757(7) Uani 1 1 d . . .
Sn1 Sn 0.44711(4) 0.46056(13) 0.35774(13) 0.0559(4) Uani 1 1 d . . .
Sn2 Sn 0.30299(4) 0.18865(14) -0.13050(12) 0.0553(4) Uani 1 1 d . . .
N3 N 0.2532(6) -0.0526(18) -0.1559(18) 0.081(5) Uani 1 1 d . . .
C13 C 0.2731(8) -0.119(2) -0.054(2) 0.077(3) Uani 1 1 d . . .
N4 N 0.3214(5) 0.4585(17) -0.2286(14) 0.051(4) Uani 1 1 d . . .
C18 C 0.3497(6) 0.489(2) -0.136(2) 0.066(3) Uani 1 1 d . . .
C19 C 0.3719(6) 0.617(2) -0.130(2) 0.066(3) Uani 1 1 d . . .
H19 H 0.3916 0.6372 -0.0658 0.079 Uiso 1 1 calc R . .
C14 C 0.2597(7) -0.250(2) -0.025(2) 0.077(3) Uani 1 1 d . . .
H14 H 0.2724 -0.2943 0.0418 0.092 Uiso 1 1 calc R . .
C15 C 0.2265(7) -0.317(2) -0.0970(19) 0.077(3) Uani 1 1 d . . .
H15 H 0.2178 -0.4078 -0.0791 0.092 Uiso 1 1 calc R . .
C22 C 0.3140(7) 0.554(2) -0.314(2) 0.066(3) Uani 1 1 d . . .
H22 H 0.2932 0.5326 -0.3753 0.079 Uiso 1 1 calc R . .
C21 C 0.3332(6) 0.674(2) -0.3173(19) 0.066(3) Uani 1 1 d . . .
H21 H 0.3270 0.7344 -0.3812 0.079 Uiso 1 1 calc R . .
C20 C 0.3644(7) 0.714(2) -0.2222(17) 0.066(3) Uani 1 1 d . . .
H20 H 0.3787 0.8004 -0.2220 0.079 Uiso 1 1 calc R . .
C16 C 0.2067(8) -0.248(3) -0.1956(19) 0.077(3) Uani 1 1 d . . .
H16 H 0.1830 -0.2871 -0.2407 0.092 Uiso 1 1 calc R . .
C17 C 0.2228(7) -0.125(2) -0.222(2) 0.077(3) Uani 1 1 d . . .
H17A H 0.2122 -0.0839 -0.2926 0.092 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
C1 0.057(6) 0.064(7) 0.075(7) 0.007(6) -0.004(6) 0.008(6)
C2 0.057(6) 0.064(7) 0.075(7) 0.007(6) -0.004(6) 0.008(6)
C3 0.057(6) 0.064(7) 0.075(7) 0.007(6) -0.004(6) 0.008(6)
C4 0.057(6) 0.064(7) 0.075(7) 0.007(6) -0.004(6) 0.008(6)
C5 0.057(6) 0.064(7) 0.075(7) 0.007(6) -0.004(6) 0.008(6)
N1 0.075(11) 0.051(12) 0.059(11) -0.015(9) -0.008(10) 0.015(10)
C6 0.063(7) 0.066(8) 0.076(8) 0.005(7) -0.003(6) 0.000(6)
C7 0.063(7) 0.066(8) 0.076(8) 0.005(7) -0.003(6) 0.000(6)
C8 0.063(7) 0.066(8) 0.076(8) 0.005(7) -0.003(6) 0.000(6)
C9 0.063(7) 0.066(8) 0.076(8) 0.005(7) -0.003(6) 0.000(6)
C10 0.063(7) 0.066(8) 0.076(8) 0.005(7) -0.003(6) 0.000(6)
N2 0.066(11) 0.057(12) 0.073(12) 0.008(10) -0.028(10) 0.016(9)
C11 0.072(14) 0.084(17) 0.058(13) 0.013(12) 0.015(12) 0.006(12)
C12 0.073(15) 0.076(16) 0.12(2) 0.002(16) 0.021(16) 0.005(13)
C23 0.061(13) 0.075(16) 0.10(2) 0.010(15) 0.023(14) 0.002(11)
C24 0.085(16) 0.089(18) 0.10(2) 0.000(16) 0.006(15) 0.027(15)
Se1 0.0687(14) 0.0665(15) 0.0615(13) -0.0081(13) -0.0130(13) 0.0007(13)
Se2 0.0750(15) 0.0672(16) 0.0579(14) -0.0041(12) -0.0094(14) 0.0135(13)
Se3 0.0730(16) 0.0781(18) 0.0684(16) 0.0109(14) -0.0111(14) -0.0027(14)
Se4 0.0805(17) 0.0800(17) 0.0665(16) 0.0118(13) -0.0228(14) -0.0155(13)
Sn1 0.0543(8) 0.0592(9) 0.0541(8) 0.0000(9) 0.0036(9) -0.0023(7)
Sn2 0.0478(8) 0.0650(9) 0.0530(9) -0.0035(10) -0.0024(9) 0.0038(8)
N3 0.076(12) 0.073(13) 0.094(14) -0.041(12) -0.007(13) -0.018(10)
C13 0.079(8) 0.067(9) 0.084(8) -0.015(7) 0.022(7) -0.013(6)
N4 0.039(9) 0.051(11) 0.063(11) -0.007(9) -0.006(9) -0.001(9)
C18 0.058(7) 0.075(8) 0.066(6) 0.010(7) -0.006(6) -0.006(6)
C19 0.058(7) 0.075(8) 0.066(6) 0.010(7) -0.006(6) -0.006(6)
C14 0.079(8) 0.067(9) 0.084(8) -0.015(7) 0.022(7) -0.013(6)
C15 0.079(8) 0.067(9) 0.084(8) -0.015(7) 0.022(7) -0.013(6)
C22 0.058(7) 0.075(8) 0.066(6) 0.010(7) -0.006(6) -0.006(6)
C21 0.058(7) 0.075(8) 0.066(6) 0.010(7) -0.006(6) -0.006(6)
C20 0.058(7) 0.075(8) 0.066(6) 0.010(7) -0.006(6) -0.006(6)
C16 0.079(8) 0.067(9) 0.084(8) -0.015(7) 0.022(7) -0.013(6)
C17 0.079(8) 0.067(9) 0.084(8) -0.015(7) 0.022(7) -0.013(6)

_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 1.35(2) . ?
C1 C2 1.42(2) . ?
C1 Se1 1.89(2) . ?
C2 C3 1.42(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.31(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.40(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.38(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.33(2) . ?
C6 C7 1.33(3) . ?
C6 Se2 1.92(2) . ?
C7 C8 1.43(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.34(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.37(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.31(2) . ?
C10 H10 0.9300 . ?
C11 Sn1 2.149(18) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 Sn1 2.122(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C23 Sn2 2.148(16) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 Sn2 2.13(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
Se1 Sn1 2.614(2) . ?
Se2 Sn1 2.616(3) . ?
Se3 C13 1.87(2) . ?
Se3 Sn2 2.595(3) . ?
Se4 C18 1.89(2) . ?
Se4 Sn2 2.584(3) . ?
N3 C17 1.34(2) . ?
N3 C13 1.41(3) . ?
C13 C14 1.35(3) . ?
N4 C22 1.33(2) . ?
N4 C18 1.35(2) . ?
C18 C19 1.39(2) . ?
C19 C20 1.40(3) . ?
C19 H19 0.9300 . ?
C14 C15 1.41(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.40(3) . ?
C15 H15 0.9300 . ?
C22 C21 1.28(2) . ?
C22 H22 0.9300 . ?
C21 C20 1.44(2) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C16 C17 1.30(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9300 . ?

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 C2 122(2) . . ?
N1 C1 Se1 114.0(15) . . ?
C2 C1 Se1 124.2(17) . . ?
C3 C2 C1 118(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 119(2) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 122(2) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
N1 C5 C4 121(2) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 N1 C5 117.7(17) . . ?
N2 C6 C7 123(2) . . ?
N2 C6 Se2 113.1(17) . . ?
C7 C6 Se2 124.1(19) . . ?
C6 C7 C8 119(2) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C9 117(2) . . ?
C7 C8 H8 121.7 . . ?
C9 C8 H8 121.7 . . ?
C10 C9 C8 121(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
N2 C10 C9 122(2) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 N2 C6 119.0(19) . . ?
Sn1 C11 H11A 109.5 . . ?
Sn1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Sn1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Sn1 C12 H12A 109.5 . . ?
Sn1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Sn1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Sn2 C23 H23A 109.5 . . ?
Sn2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Sn2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Sn2 C24 H24A 109.5 . . ?
Sn2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
Sn2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 Se1 Sn1 86.3(7) . . ?
C6 Se2 Sn1 88.5(7) . . ?
C13 Se3 Sn2 90.0(8) . . ?
C18 Se4 Sn2 89.8(7) . . ?
C12 Sn1 C11 130.1(9) . . ?
C12 Sn1 Se1 106.3(6) . . ?
C11 Sn1 Se1 106.4(5) . . ?
C12 Sn1 Se2 107.4(6) . . ?
C11 Sn1 Se2 106.6(5) . . ?
Se1 Sn1 Se2 94.25(8) . . ?
C24 Sn2 C23 127.3(8) . . ?
C24 Sn2 Se4 106.0(6) . . ?
C23 Sn2 Se4 109.6(6) . . ?
C24 Sn2 Se3 107.1(6) . . ?
C23 Sn2 Se3 109.6(6) . . ?
Se4 Sn2 Se3 91.23(8) . . ?
C17 N3 C13 118(2) . . ?
C14 C13 N3 119(2) . . ?
C14 C13 Se3 128(2) . . ?
N3 C13 Se3 113.1(16) . . ?
C22 N4 C18 118.8(18) . . ?
N4 C18 C19 121(2) . . ?
N4 C18 Se4 117.5(15) . . ?
C19 C18 Se4 121.7(17) . . ?
C18 C19 C20 119(2) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C13 C14 C15 120(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C21 C22 N4 125(2) . . ?
C21 C22 H22 117.5 . . ?
N4 C22 H22 117.5 . . ?
C22 C21 C20 120(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C19 C20 C21 116(2) . . ?
C19 C20 H20 121.8 . . ?
C21 C20 H20 121.8 . . ?
C17 C16 C15 117(2) . . ?
C17 C16 H16 121.5 . . ?
C15 C16 H16 121.5 . . ?
C16 C17 N3 126(2) . . ?
C16 C17 H17A 116.8 . . ?
N3 C17 H17A 116.8 . . ?

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 C1 C2 C3 0(3) . . . . ?
Se1 C1 C2 C3 178.5(13) . . . . ?
C1 C2 C3 C4 3(3) . . . . ?
C2 C3 C4 C5 -6(3) . . . . ?
C3 C4 C5 N1 7(3) . . . . ?
C2 C1 N1 C5 1(3) . . . . ?
Se1 C1 N1 C5 -178.3(14) . . . . ?
C4 C5 N1 C1 -4(3) . . . . ?
N2 C6 C7 C8 -5(3) . . . . ?
Se2 C6 C7 C8 -178.2(14) . . . . ?
C6 C7 C8 C9 0(3) . . . . ?
C7 C8 C9 C10 4(3) . . . . ?
C8 C9 C10 N2 -4(3) . . . . ?
C9 C10 N2 C6 -1(3) . . . . ?
C7 C6 N2 C10 6(3) . . . . ?
Se2 C6 N2 C10 179.3(13) . . . . ?
N1 C1 Se1 Sn1 -3.1(14) . . . . ?
C2 C1 Se1 Sn1 178.0(18) . . . . ?
N2 C6 Se2 Sn1 2.7(14) . . . . ?
C7 C6 Se2 Sn1 176.4(19) . . . . ?
C1 Se1 Sn1 C12 -67.2(10) . . . . ?
C1 Se1 Sn1 C11 74.7(9) . . . . ?
C1 Se1 Sn1 Se2 -176.7(6) . . . . ?
C6 Se2 Sn1 C12 69.0(9) . . . . ?
C6 Se2 Sn1 C11 -73.9(8) . . . . ?
C6 Se2 Sn1 Se1 177.5(6) . . . . ?
C18 Se4 Sn2 C24 71.0(9) . . . . ?
C18 Se4 Sn2 C23 -69.5(9) . . . . ?
C18 Se4 Sn2 Se3 179.2(6) . . . . ?
C13 Se3 Sn2 C24 -75.0(9) . . . . ?
C13 Se3 Sn2 C23 66.4(9) . . . . ?
C13 Se3 Sn2 Se4 177.8(7) . . . . ?
C17 N3 C13 C14 -2(3) . . . . ?
C17 N3 C13 Se3 178.2(14) . . . . ?
Sn2 Se3 C13 C14 179(2) . . . . ?
Sn2 Se3 C13 N3 -0.7(15) . . . . ?
C22 N4 C18 C19 -2(3) . . . . ?
C22 N4 C18 Se4 -179.5(14) . . . . ?
Sn2 Se4 C18 N4 -2.1(14) . . . . ?
Sn2 Se4 C18 C19 -179.7(17) . . . . ?
N4 C18 C19 C20 0(3) . . . . ?
Se4 C18 C19 C20 177.9(14) . . . . ?
N3 C13 C14 C15 0(3) . . . . ?
Se3 C13 C14 C15 180.0(14) . . . . ?
C13 C14 C15 C16 -2(3) . . . . ?
C18 N4 C22 C21 3(3) . . . . ?
N4 C22 C21 C20 -2(3) . . . . ?
C18 C19 C20 C21 0(3) . . . . ?
C22 C21 C20 C19 0(3) . . . . ?
C14 C15 C16 C17 5(3) . . . . ?
C15 C16 C17 N3 -7(3) . . . . ?
C13 N3 C17 C16 6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.716
_refine_diff_density_min         -1.129
_refine_diff_density_rms         0.202


data_Sn(SepyMe)Me2Cl
_database_code_depnum_ccdc_archive 'CCDC 880460'
#TrackingRef 'RS-9.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 Cl N Se Sn'
_chemical_formula_weight         355.29

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'
Se Se -0.0929 2.2259 '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 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   10.146(3)
_cell_length_b                   9.916(3)
_cell_length_c                   13.060(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.521(19)
_cell_angle_gamma                90.00
_cell_volume                     1213.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7.9
_cell_measurement_theta_max      12.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    5.279
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.2266
_exptl_absorpt_correction_T_max  0.6203


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S'
_diffrn_measurement_method       \w-2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -8.05
_diffrn_reflns_number            3354
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.1806
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         27.54
_reflns_number_total             2797
_reflns_number_gt                1028
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep 3 for windows'
_computing_publication_material  'WinGX 1.70.01'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0169P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         2797
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2079
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_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
Sn1 Sn 0.16612(7) 0.15102(8) 0.86984(6) 0.0550(3) Uani 1 1 d . . .
Se1 Se 0.40581(11) 0.14351(12) 1.03607(9) 0.0639(4) Uani 1 1 d . . .
Cl1 Cl 0.1570(3) -0.0925(3) 0.8331(3) 0.1002(12) Uani 1 1 d . . .
N1 N 0.2475(9) 0.3680(9) 0.9567(7) 0.058(2) Uani 1 1 d . . .
C1 C 0.3696(11) 0.3327(11) 1.0409(9) 0.055(3) Uani 1 1 d . . .
C7 C -0.0208(10) 0.1644(11) 0.9051(8) 0.076(4) Uani 1 1 d . . .
H7A H -0.0833 0.2316 0.8584 0.114 Uiso 1 1 calc R . .
H7B H 0.0047 0.1888 0.9814 0.114 Uiso 1 1 calc R . .
H7C H -0.0686 0.0787 0.8914 0.114 Uiso 1 1 calc R . .
C5 C 0.2082(14) 0.4967(14) 0.9504(11) 0.085(4) Uani 1 1 d . . .
H5 H 0.1228 0.5218 0.8941 0.101 Uiso 1 1 calc R . .
C3 C 0.4137(14) 0.5557(13) 1.1090(10) 0.078(4) Uani 1 1 d . . .
H3 H 0.4681 0.6199 1.1594 0.094 Uiso 1 1 calc R . .
C2 C 0.4584(12) 0.4229(11) 1.1202(10) 0.061(3) Uani 1 1 d . . .
C4 C 0.2866(16) 0.5946(13) 1.0223(13) 0.091(4) Uani 1 1 d . . .
H4 H 0.2566 0.6840 1.0140 0.109 Uiso 1 1 calc R . .
C8 C 0.1828(10) 0.2155(13) 0.7207(8) 0.084(4) Uani 1 1 d . . .
H8A H 0.1686 0.1399 0.6717 0.126 Uiso 1 1 calc R . .
H8B H 0.2758 0.2531 0.7369 0.126 Uiso 1 1 calc R . .
H8C H 0.1115 0.2827 0.6860 0.126 Uiso 1 1 calc R . .
C6 C 0.5886(11) 0.3765(11) 1.2128(8) 0.075(4) Uani 1 1 d . . .
H6A H 0.6548 0.4500 1.2383 0.113 Uiso 1 1 calc R . .
H6B H 0.6318 0.3044 1.1878 0.113 Uiso 1 1 calc R . .
H6C H 0.5635 0.3451 1.2725 0.113 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 0.0512(4) 0.0640(5) 0.0487(4) -0.0007(5) 0.0177(3) 0.0012(5)
Se1 0.0587(7) 0.0508(7) 0.0681(8) -0.0012(7) 0.0086(6) 0.0088(7)
Cl1 0.097(3) 0.071(2) 0.116(3) -0.025(2) 0.022(2) -0.005(2)
N1 0.068(6) 0.045(6) 0.059(6) 0.004(5) 0.024(5) 0.014(5)
C1 0.062(7) 0.054(8) 0.056(7) 0.010(6) 0.032(6) 0.008(6)
C7 0.056(7) 0.112(10) 0.067(7) 0.000(8) 0.032(6) -0.011(7)
C5 0.114(12) 0.072(10) 0.079(10) 0.009(9) 0.050(9) 0.023(9)
C3 0.102(10) 0.062(10) 0.077(9) -0.006(8) 0.042(8) 0.000(8)
C2 0.069(8) 0.037(7) 0.080(8) -0.016(7) 0.031(7) -0.007(6)
C4 0.121(13) 0.039(8) 0.121(12) -0.001(9) 0.056(10) 0.018(8)
C8 0.073(8) 0.132(12) 0.058(7) -0.004(8) 0.037(6) -0.004(8)
C6 0.069(8) 0.078(9) 0.067(8) -0.006(7) 0.013(6) -0.019(7)

_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 C8 2.117(9) . ?
Sn1 C7 2.120(9) . ?
Sn1 N1 2.425(9) . ?
Sn1 Cl1 2.457(3) . ?
Sn1 Se1 2.5667(14) . ?
Se1 C1 1.917(11) . ?
N1 C5 1.330(13) . ?
N1 C1 1.350(12) . ?
C1 C2 1.404(13) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C5 C4 1.374(15) . ?
C5 H5 0.9300 . ?
C3 C2 1.382(14) . ?
C3 C4 1.405(15) . ?
C3 H3 0.9300 . ?
C2 C6 1.482(13) . ?
C4 H4 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 Sn1 C7 125.0(4) . . ?
C8 Sn1 N1 91.7(4) . . ?
C7 Sn1 N1 90.9(4) . . ?
C8 Sn1 Cl1 97.3(4) . . ?
C7 Sn1 Cl1 97.7(3) . . ?
N1 Sn1 Cl1 160.7(2) . . ?
C8 Sn1 Se1 113.8(3) . . ?
C7 Sn1 Se1 117.0(3) . . ?
N1 Sn1 Se1 65.6(2) . . ?
Cl1 Sn1 Se1 95.12(9) . . ?
C1 Se1 Sn1 82.4(3) . . ?
C5 N1 C1 117.3(11) . . ?
C5 N1 Sn1 141.4(9) . . ?
C1 N1 Sn1 101.1(7) . . ?
N1 C1 C2 124.4(10) . . ?
N1 C1 Se1 110.8(8) . . ?
C2 C1 Se1 124.8(8) . . ?
Sn1 C7 H7A 109.5 . . ?
Sn1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Sn1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C5 C4 123.7(12) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C2 C3 C4 120.6(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C2 C1 115.9(11) . . ?
C3 C2 C6 122.4(11) . . ?
C1 C2 C6 121.6(10) . . ?
C5 C4 C3 118.0(12) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
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 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C8 Sn1 Se1 C1 81.9(5) . . . . ?
C7 Sn1 Se1 C1 -76.5(4) . . . . ?
N1 Sn1 Se1 C1 1.3(3) . . . . ?
Cl1 Sn1 Se1 C1 -177.8(3) . . . . ?
C8 Sn1 N1 C5 67.1(12) . . . . ?
C7 Sn1 N1 C5 -57.9(12) . . . . ?
Cl1 Sn1 N1 C5 -174.8(9) . . . . ?
Se1 Sn1 N1 C5 -177.4(12) . . . . ?
C8 Sn1 N1 C1 -117.3(6) . . . . ?
C7 Sn1 N1 C1 117.6(6) . . . . ?
Cl1 Sn1 N1 C1 0.8(10) . . . . ?
Se1 Sn1 N1 C1 -1.9(5) . . . . ?
C5 N1 C1 C2 -1.4(15) . . . . ?
Sn1 N1 C1 C2 -178.2(8) . . . . ?
C5 N1 C1 Se1 179.3(8) . . . . ?
Sn1 N1 C1 Se1 2.5(6) . . . . ?
Sn1 Se1 C1 N1 -2.3(6) . . . . ?
Sn1 Se1 C1 C2 178.4(9) . . . . ?
C1 N1 C5 C4 1.9(17) . . . . ?
Sn1 N1 C5 C4 177.0(9) . . . . ?
C4 C3 C2 C1 -0.2(17) . . . . ?
C4 C3 C2 C6 -177.5(10) . . . . ?
N1 C1 C2 C3 0.6(16) . . . . ?
Se1 C1 C2 C3 179.8(8) . . . . ?
N1 C1 C2 C6 177.9(9) . . . . ?
Se1 C1 C2 C6 -2.9(14) . . . . ?
N1 C5 C4 C3 -1.7(19) . . . . ?
C2 C3 C4 C5 0.8(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.613
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.148


data_Sn(Sepy)2(But)2
_database_code_depnum_ccdc_archive 'CCDC 880461'
#TrackingRef 'RS-10.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 N2 Se2 Sn'
_chemical_formula_weight         547.02

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'
Se Se -0.0929 2.2259 '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   C2

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

_cell_length_a                   15.500(6)
_cell_length_b                   7.312(4)
_cell_length_c                   10.354(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.97(3)
_cell_angle_gamma                90.00
_cell_volume                     1045.9(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7.9
_cell_measurement_theta_max      11.6

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    4.703
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.2549
_exptl_absorpt_correction_T_max  0.6506


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  'Rigaku AFC7S'
_diffrn_measurement_method       \w-2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -3.84
_diffrn_reflns_number            1571
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0763
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         27.53
_reflns_number_total             1307
_reflns_number_gt                974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep 3 for windows'
_computing_publication_material  'WinGX 1.70.01'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0167P)^2^+2.7390P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.70(7)
_refine_ls_number_reflns         1307
_refine_ls_number_parameters     109
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_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
Sn1 Sn 0.5000 0.08876(14) 0.0000 0.0333(2) Uani 1 2 d S . .
Se1 Se 0.61693(8) -0.1667(3) 0.16446(13) 0.0500(4) Uani 1 1 d . . .
N1 N 0.6795(7) 0.1900(15) 0.2318(11) 0.047(3) Uani 1 1 d . . .
C1 C 0.7074(8) 0.016(2) 0.2723(14) 0.044(3) Uani 1 1 d . . .
C2 C 0.7966(8) -0.024(2) 0.3876(13) 0.056(3) Uani 1 1 d . . .
H2 H 0.8147 -0.1447 0.4162 0.067 Uiso 1 1 calc R . .
C7 C 0.5047(9) 0.165(2) -0.2927(11) 0.070(4) Uani 1 1 d . . .
H7A H 0.5363 0.2094 -0.3476 0.105 Uiso 1 1 calc R . .
H7B H 0.4419 0.2208 -0.3281 0.105 Uiso 1 1 calc R . .
H7C H 0.4976 0.0348 -0.3027 0.105 Uiso 1 1 calc R . .
C4 C 0.8315(10) 0.296(2) 0.4199(15) 0.073(5) Uani 1 1 d . . .
H4 H 0.8726 0.3923 0.4689 0.088 Uiso 1 1 calc R . .
C3 C 0.8571(9) 0.118(3) 0.4579(14) 0.072(5) Uani 1 1 d . . .
H3 H 0.9176 0.0923 0.5340 0.086 Uiso 1 1 calc R . .
C6 C 0.5649(7) 0.2139(17) -0.1341(11) 0.041(3) Uani 1 1 d . . .
C9 C 0.6648(7) 0.139(2) -0.0863(14) 0.070(4) Uani 1 1 d . . .
H9A H 0.6901 0.1832 -0.1497 0.104 Uiso 1 1 calc R . .
H9B H 0.6624 0.0081 -0.0894 0.104 Uiso 1 1 calc R . .
H9C H 0.7060 0.1787 0.0110 0.104 Uiso 1 1 calc R . .
C5 C 0.7405(9) 0.326(2) 0.3037(13) 0.064(3) Uani 1 1 d . . .
H5 H 0.7213 0.4459 0.2747 0.077 Uiso 1 1 calc R . .
C8 C 0.5694(10) 0.4171(17) -0.1105(16) 0.067(4) Uani 1 1 d . . .
H8A H 0.6035 0.4427 -0.0086 0.101 Uiso 1 1 calc R . .
H8B H 0.5048 0.4653 -0.1487 0.101 Uiso 1 1 calc R . .
H8C H 0.6026 0.4732 -0.1590 0.101 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 0.0323(5) 0.0292(5) 0.0391(6) 0.000 0.0167(4) 0.000
Se1 0.0449(7) 0.0344(7) 0.0590(9) 0.0043(6) 0.0133(6) 0.0057(5)
N1 0.050(6) 0.040(6) 0.046(6) -0.012(5) 0.017(5) -0.001(5)
C1 0.033(6) 0.057(8) 0.039(7) -0.003(6) 0.014(5) 0.010(5)
C2 0.045(6) 0.068(9) 0.048(8) 0.015(7) 0.016(6) 0.008(7)
C7 0.084(9) 0.092(11) 0.045(7) -0.012(7) 0.040(7) -0.029(8)
C4 0.079(10) 0.078(12) 0.058(9) -0.023(9) 0.028(8) -0.029(9)
C3 0.046(6) 0.093(14) 0.066(8) -0.024(11) 0.016(6) -0.011(9)
C6 0.029(5) 0.057(7) 0.037(6) 0.001(5) 0.015(4) -0.008(5)
C9 0.051(6) 0.091(13) 0.089(9) 0.007(8) 0.051(7) 0.008(7)
C5 0.082(8) 0.053(7) 0.064(8) -0.011(8) 0.038(7) -0.019(8)
C8 0.098(10) 0.043(7) 0.083(10) -0.002(7) 0.061(9) -0.017(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 C6 2.246(10) . ?
Sn1 C6 2.246(10) 2_655 ?
Sn1 Se1 2.622(2) 2_655 ?
Sn1 Se1 2.622(2) . ?
Se1 C1 1.893(14) . ?
N1 C5 1.342(16) . ?
N1 C1 1.344(14) . ?
C1 C2 1.389(15) . ?
C2 C3 1.37(2) . ?
C2 H2 0.9300 . ?
C7 C6 1.518(14) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C4 C3 1.37(2) . ?
C4 C5 1.395(17) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C6 C9 1.499(14) . ?
C6 C8 1.502(15) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 Sn1 C6 131.9(6) . 2_655 ?
C6 Sn1 Se1 105.1(3) . 2_655 ?
C6 Sn1 Se1 108.7(3) 2_655 2_655 ?
C6 Sn1 Se1 108.7(3) . . ?
C6 Sn1 Se1 105.1(3) 2_655 . ?
Se1 Sn1 Se1 89.14(11) 2_655 . ?
C1 Se1 Sn1 89.3(4) . . ?
C5 N1 C1 118.7(11) . . ?
N1 C1 C2 121.6(12) . . ?
N1 C1 Se1 115.9(9) . . ?
C2 C1 Se1 122.5(11) . . ?
C3 C2 C1 118.0(14) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C4 C5 116.5(14) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C2 C3 C4 122.2(14) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C9 C6 C8 110.0(11) . . ?
C9 C6 C7 108.0(10) . . ?
C8 C6 C7 111.6(12) . . ?
C9 C6 Sn1 109.5(8) . . ?
C8 C6 Sn1 107.6(8) . . ?
C7 C6 Sn1 110.2(7) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C5 C4 123.0(16) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C6 Sn1 Se1 C1 69.0(5) . . . . ?
C6 Sn1 Se1 C1 -76.2(5) 2_655 . . . ?
Se1 Sn1 Se1 C1 174.7(4) 2_655 . . . ?
C5 N1 C1 C2 1(2) . . . . ?
C5 N1 C1 Se1 -179.7(8) . . . . ?
Sn1 Se1 C1 N1 2.0(12) . . . . ?
Sn1 Se1 C1 C2 -178.9(11) . . . . ?
N1 C1 C2 C3 -1(2) . . . . ?
Se1 C1 C2 C3 179.5(10) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C5 C4 C3 C2 -1(2) . . . . ?
C6 Sn1 C6 C9 125.5(9) 2_655 . . . ?
Se1 Sn1 C6 C9 -101.1(8) 2_655 . . . ?
Se1 Sn1 C6 C9 -6.8(9) . . . . ?
C6 Sn1 C6 C8 6.0(8) 2_655 . . . ?
Se1 Sn1 C6 C8 139.4(9) 2_655 . . . ?
Se1 Sn1 C6 C8 -126.3(9) . . . . ?
C6 Sn1 C6 C7 -115.9(9) 2_655 . . . ?
Se1 Sn1 C6 C7 17.5(9) 2_655 . . . ?
Se1 Sn1 C6 C7 111.8(9) . . . . ?
C1 N1 C5 C4 -1(2) . . . . ?
C3 C4 C5 N1 1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.691
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.149