# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_naka217
_database_code_depnum_ccdc_archive 'CCDC 1535386'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C14 H23 Cl Ge N2 S' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H23 Cl Ge N2 S'
_chemical_formula_sum            'C14 H23 Cl Ge N2 S'
_chemical_formula_weight         359.44

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 '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'
_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                   13.004(4)
_cell_length_b                   11.372(4)
_cell_length_c                   11.580(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.447(4)
_cell_angle_gamma                90.00
_cell_volume                     1707.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2588
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.07

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.063
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8862
_exptl_absorpt_correction_T_max  0.9039
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8001
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3110
_reflns_number_gt                2464
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.1087P)²+5.4781P] 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         3110
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1994
_refine_ls_wR_factor_gt          0.1951
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Ge1 Ge 0.73435(5) 0.11503(6) 0.04467(6) 0.0209(3) Uani 1 1 d . . .
S1 S 0.74823(12) 0.29940(13) 0.19571(14) 0.0182(4) Uani 1 1 d . . .
Cl1 Cl 0.73223(14) -0.03030(14) 0.18871(16) 0.0316(4) Uani 1 1 d . . .
C8 C 0.7583(5) 0.6778(6) 0.0770(6) 0.0253(15) Uani 1 1 d . . .
H12 H 0.7593 0.7575 0.0524 0.030 Uiso 1 1 calc R . .
C6 C 0.7627(5) 0.4725(6) 0.0311(6) 0.0279(15) Uani 1 1 d . . .
H10 H 0.7666 0.4107 -0.0236 0.033 Uiso 1 1 calc R . .
N1 N 0.8331(4) 0.2266(4) 0.1238(5) 0.0194(11) Uani 1 1 d . . .
N2 N 0.6527(4) 0.2376(5) 0.1160(5) 0.0199(11) Uani 1 1 d . . .
C5 C 0.7534(5) 0.4477(5) 0.1455(6) 0.0203(13) Uani 1 1 d . . .
C7 C 0.7664(5) 0.5885(7) -0.0039(6) 0.0305(16) Uani 1 1 d . . .
H11 H 0.7743 0.6071 -0.0827 0.037 Uiso 1 1 calc R . .
C10 C 0.7467(5) 0.5357(6) 0.2267(6) 0.0214(14) Uani 1 1 d . . .
H14 H 0.7406 0.5167 0.3057 0.026 Uiso 1 1 calc R . .
C9 C 0.7491(5) 0.6527(6) 0.1914(6) 0.0256(15) Uani 1 1 d . . .
H13 H 0.7443 0.7144 0.2460 0.031 Uiso 1 1 calc R . .
C11 C 0.5475(5) 0.2366(6) 0.1584(6) 0.0256(15) Uani 1 1 d . . .
C4 C 0.9905(5) 0.1269(6) 0.0963(7) 0.0323(17) Uani 1 1 d . . .
H7 H 0.9578 0.0495 0.1003 0.049 Uiso 1 1 calc R . .
H8 H 1.0642 0.1201 0.1203 0.049 Uiso 1 1 calc R . .
H9 H 0.9817 0.1564 0.0166 0.049 Uiso 1 1 calc R . .
C1 C 0.9404(5) 0.2115(6) 0.1762(6) 0.0252(15) Uani 1 1 d . . .
C3 C 0.9435(5) 0.1609(6) 0.2987(6) 0.0282(15) Uani 1 1 d . . .
H4 H 0.9076 0.2143 0.3485 0.042 Uiso 1 1 calc R . .
H5 H 1.0154 0.1520 0.3297 0.042 Uiso 1 1 calc R . .
H6 H 0.9094 0.0840 0.2966 0.042 Uiso 1 1 calc R . .
C14 C 0.4857(5) 0.1480(6) 0.0823(7) 0.0307(16) Uani 1 1 d . . .
H21 H 0.4855 0.1720 0.0010 0.046 Uiso 1 1 calc R . .
H22 H 0.4147 0.1450 0.1049 0.046 Uiso 1 1 calc R . .
H23 H 0.5173 0.0700 0.0921 0.046 Uiso 1 1 calc R . .
C2 C 0.9956(5) 0.3313(7) 0.1791(8) 0.0364(18) Uani 1 1 d . . .
H1 H 1.0001 0.3596 0.0997 0.055 Uiso 1 1 calc R . .
H2 H 1.0651 0.3226 0.2171 0.055 Uiso 1 1 calc R . .
H3 H 0.9565 0.3878 0.2222 0.055 Uiso 1 1 calc R . .
C13 C 0.5500(6) 0.1964(8) 0.2855(7) 0.041(2) Uani 1 1 d . . .
H18 H 0.5852 0.1204 0.2940 0.061 Uiso 1 1 calc R . .
H19 H 0.4792 0.1886 0.3082 0.061 Uiso 1 1 calc R . .
H20 H 0.5870 0.2547 0.3352 0.061 Uiso 1 1 calc R . .
C12 C 0.5003(6) 0.3584(7) 0.1428(10) 0.052(3) Uani 1 1 d . . .
H15 H 0.5392 0.4142 0.1937 0.078 Uiso 1 1 calc R . .
H16 H 0.4284 0.3562 0.1624 0.078 Uiso 1 1 calc R . .
H17 H 0.5029 0.3832 0.0620 0.078 Uiso 1 1 calc R . .


_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
Ge1 N2 1.972(5) . ?
Ge1 N1 1.979(5) . ?
Ge1 Cl1 2.3498(19) . ?
Ge1 S1 2.7274(17) . ?
S1 N2 1.647(5) . ?
S1 N1 1.655(5) . ?
S1 C5 1.786(6) . ?
C8 C9 1.370(10) . ?
C8 C7 1.391(10) . ?
C6 C5 1.369(10) . ?
C6 C7 1.381(10) . ?
N1 C1 1.488(8) . ?
N2 C11 1.489(8) . ?
C5 C10 1.381(9) . ?
C10 C9 1.393(9) . ?
C11 C12 1.520(11) . ?
C11 C14 1.526(9) . ?
C11 C13 1.538(10) . ?
C4 C1 1.517(9) . ?
C1 C3 1.528(10) . ?
C1 C2 1.538(9) . ?

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
N2 Ge1 N1 72.8(2) . . ?
N2 Ge1 Cl1 99.40(16) . . ?
N1 Ge1 Cl1 99.51(17) . . ?
N2 Ge1 S1 36.79(14) . . ?
N1 Ge1 S1 37.05(14) . . ?
Cl1 Ge1 S1 95.12(6) . . ?
N2 S1 N1 90.5(3) . . ?
N2 S1 C5 105.4(3) . . ?
N1 S1 C5 105.3(3) . . ?
N2 S1 Ge1 45.82(18) . . ?
N1 S1 Ge1 46.09(18) . . ?
C5 S1 Ge1 121.3(2) . . ?
C9 C8 C7 121.0(6) . . ?
C5 C6 C7 119.2(7) . . ?
C1 N1 S1 119.6(4) . . ?
C1 N1 Ge1 132.0(4) . . ?
S1 N1 Ge1 96.9(2) . . ?
C11 N2 S1 119.4(4) . . ?
C11 N2 Ge1 132.2(4) . . ?
S1 N2 Ge1 97.4(2) . . ?
C6 C5 C10 121.6(6) . . ?
C6 C5 S1 121.2(5) . . ?
C10 C5 S1 117.2(5) . . ?
C6 C7 C8 119.6(7) . . ?
C5 C10 C9 119.3(6) . . ?
C8 C9 C10 119.3(7) . . ?
N2 C11 C12 109.0(6) . . ?
N2 C11 C14 105.7(5) . . ?
C12 C11 C14 110.1(6) . . ?
N2 C11 C13 111.5(5) . . ?
C12 C11 C13 111.3(7) . . ?
C14 C11 C13 109.1(6) . . ?
N1 C1 C4 104.9(5) . . ?
N1 C1 C3 112.2(5) . . ?
C4 C1 C3 110.3(6) . . ?
N1 C1 C2 109.1(5) . . ?
C4 C1 C2 110.7(6) . . ?
C3 C1 C2 109.6(6) . . ?

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 Ge1 S1 N2 162.1(4) . . . . ?
Cl1 Ge1 S1 N2 -98.9(3) . . . . ?
N2 Ge1 S1 N1 -162.1(4) . . . . ?
Cl1 Ge1 S1 N1 99.0(3) . . . . ?
N2 Ge1 S1 C5 -81.0(4) . . . . ?
N1 Ge1 S1 C5 81.1(4) . . . . ?
Cl1 Ge1 S1 C5 -179.9(2) . . . . ?
N2 S1 N1 C1 -160.2(5) . . . . ?
C5 S1 N1 C1 93.6(5) . . . . ?
Ge1 S1 N1 C1 -147.5(6) . . . . ?
N2 S1 N1 Ge1 -12.7(3) . . . . ?
C5 S1 N1 Ge1 -118.9(3) . . . . ?
N2 Ge1 N1 C1 152.1(6) . . . . ?
Cl1 Ge1 N1 C1 55.1(6) . . . . ?
S1 Ge1 N1 C1 141.0(7) . . . . ?
N2 Ge1 N1 S1 11.1(2) . . . . ?
Cl1 Ge1 N1 S1 -85.9(2) . . . . ?
N1 S1 N2 C11 161.0(5) . . . . ?
C5 S1 N2 C11 -92.9(5) . . . . ?
Ge1 S1 N2 C11 148.2(6) . . . . ?
N1 S1 N2 Ge1 12.8(3) . . . . ?
C5 S1 N2 Ge1 118.8(3) . . . . ?
N1 Ge1 N2 C11 -152.9(6) . . . . ?
Cl1 Ge1 N2 C11 -55.8(6) . . . . ?
S1 Ge1 N2 C11 -141.8(7) . . . . ?
N1 Ge1 N2 S1 -11.2(2) . . . . ?
Cl1 Ge1 N2 S1 86.0(2) . . . . ?
C7 C6 C5 C10 0.6(10) . . . . ?
C7 C6 C5 S1 179.9(5) . . . . ?
N2 S1 C5 C6 -55.0(6) . . . . ?
N1 S1 C5 C6 39.9(6) . . . . ?
Ge1 S1 C5 C6 -7.7(6) . . . . ?
N2 S1 C5 C10 124.4(5) . . . . ?
N1 S1 C5 C10 -140.7(5) . . . . ?
Ge1 S1 C5 C10 171.7(4) . . . . ?
C5 C6 C7 C8 -1.4(10) . . . . ?
C9 C8 C7 C6 1.4(10) . . . . ?
C6 C5 C10 C9 0.2(9) . . . . ?
S1 C5 C10 C9 -179.2(5) . . . . ?
C7 C8 C9 C10 -0.6(10) . . . . ?
C5 C10 C9 C8 -0.2(9) . . . . ?
S1 N2 C11 C12 75.8(7) . . . . ?
Ge1 N2 C11 C12 -149.0(6) . . . . ?
S1 N2 C11 C14 -165.9(5) . . . . ?
Ge1 N2 C11 C14 -30.7(8) . . . . ?
S1 N2 C11 C13 -47.5(7) . . . . ?
Ge1 N2 C11 C13 87.7(7) . . . . ?
S1 N1 C1 C4 171.8(4) . . . . ?
Ge1 N1 C1 C4 37.7(8) . . . . ?
S1 N1 C1 C3 52.0(7) . . . . ?
Ge1 N1 C1 C3 -82.0(7) . . . . ?
S1 N1 C1 C2 -69.6(7) . . . . ?
Ge1 N1 C1 C2 156.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         2.735
_refine_diff_density_min         -1.206
_refine_diff_density_rms         0.161
####################################################################### 
# 
# 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_naka289
_database_code_depnum_ccdc_archive 'CCDC 1535387'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C14 H23 Cl N2 S Sn' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H23 Cl N2 S Sn'
_chemical_formula_sum            'C14 H23 Cl N2 S Sn'
_chemical_formula_weight         405.54

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'
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           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_Int_Tables_number      62

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

_cell_length_a                   11.9462(12)
_cell_length_b                   12.6983(13)
_cell_length_c                   11.6365(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1765.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5813
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.59

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    1.707
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8615
_exptl_absorpt_correction_T_max  0.9045
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8968
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         26.50
_reflns_number_total             1903
_reflns_number_gt                1745
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0272P)²+0.1823P] 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         1903
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0534
_refine_ls_wR_factor_gt          0.0524
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.023902(13) 0.2500 0.106686(13) 0.02017(8) Uani 1 2 d S . .
S1 S 0.18441(5) 0.2500 0.29615(5) 0.01663(13) Uani 1 2 d S . .
Cl1 Cl 0.16538(6) 0.2500 -0.04972(5) 0.02941(16) Uani 1 2 d S . .
C5 C 0.1283(2) 0.2500 0.4396(2) 0.0177(5) Uani 1 2 d S . .
C6 C 0.2037(2) 0.2500 0.53020(19) 0.0196(5) Uani 1 2 d S . .
H10 H 0.2820 0.2500 0.5159 0.024 Uiso 1 2 calc SR . .
C8 C 0.0495(2) 0.2500 0.6620(2) 0.0242(5) Uani 1 2 d S . .
H12 H 0.0221 0.2500 0.7386 0.029 Uiso 1 2 calc SR . .
N1 N 0.11704(11) 0.15570(11) 0.22927(11) 0.0189(3) Uani 1 1 d . . .
C7 C 0.1630(2) 0.2500 0.6425(2) 0.0230(5) Uani 1 2 d S . .
H11 H 0.2136 0.2500 0.7055 0.028 Uiso 1 2 calc SR . .
C1 C 0.16930(15) 0.04952(14) 0.22283(15) 0.0236(4) Uani 1 1 d . . .
C9 C -0.0261(2) 0.2500 0.5703(3) 0.0285(6) Uani 1 2 d S . .
H13 H -0.1044 0.2500 0.5846 0.034 Uiso 1 2 calc SR . .
C10 C 0.0137(2) 0.2500 0.4583(2) 0.0239(6) Uani 1 2 d S . .
H14 H -0.0369 0.2500 0.3953 0.029 Uiso 1 2 calc SR . .
C3 C 0.09306(17) -0.01435(16) 0.14468(18) 0.0325(4) Uani 1 1 d . . .
H4 H 0.0174 -0.0162 0.1772 0.049 Uiso 1 1 calc R . .
H5 H 0.1220 -0.0863 0.1380 0.049 Uiso 1 1 calc R . .
H6 H 0.0907 0.0183 0.0684 0.049 Uiso 1 1 calc R . .
C2 C 0.1745(2) 0.00008(17) 0.34209(17) 0.0402(5) Uani 1 1 d . . .
H1 H 0.2229 0.0426 0.3917 0.060 Uiso 1 1 calc R . .
H2 H 0.2048 -0.0714 0.3362 0.060 Uiso 1 1 calc R . .
H3 H 0.0990 -0.0028 0.3750 0.060 Uiso 1 1 calc R . .
C4 C 0.28721(16) 0.05501(15) 0.16981(18) 0.0301(4) Uani 1 1 d . . .
H7 H 0.2831 0.0890 0.0943 0.045 Uiso 1 1 calc R . .
H8 H 0.3171 -0.0164 0.1611 0.045 Uiso 1 1 calc R . .
H9 H 0.3365 0.0959 0.2202 0.045 Uiso 1 1 calc R . .


_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 N1 2.1694(14) . ?
Sn1 N1 2.1695(14) 8_565 ?
Sn1 Cl1 2.4837(7) . ?
Sn1 S1 2.9219(6) . ?
S1 N1 1.6393(14) 8_565 ?
S1 N1 1.6393(14) . ?
S1 C5 1.799(2) . ?
C5 C10 1.386(3) . ?
C5 C6 1.386(3) . ?
C6 C7 1.395(3) . ?
C8 C7 1.374(4) . ?
C8 C9 1.397(4) . ?
N1 C1 1.488(2) . ?
C1 C3 1.521(2) . ?
C1 C2 1.524(3) . ?
C1 C4 1.539(3) . ?
C9 C10 1.388(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
N1 Sn1 N1 67.00(7) . 8_565 ?
N1 Sn1 Cl1 97.63(4) . . ?
N1 Sn1 Cl1 97.63(4) 8_565 . ?
N1 Sn1 S1 33.62(4) . . ?
N1 Sn1 S1 33.62(4) 8_565 . ?
Cl1 Sn1 S1 96.11(2) . . ?
N1 S1 N1 93.85(10) 8_565 . ?
N1 S1 C5 104.93(7) 8_565 . ?
N1 S1 C5 104.93(7) . . ?
N1 S1 Sn1 47.12(5) 8_565 . ?
N1 S1 Sn1 47.12(5) . . ?
C5 S1 Sn1 117.11(8) . . ?
C10 C5 C6 121.5(2) . . ?
C10 C5 S1 120.88(19) . . ?
C6 C5 S1 117.60(18) . . ?
C5 C6 C7 119.1(2) . . ?
C7 C8 C9 120.7(2) . . ?
C1 N1 S1 118.68(11) . . ?
C1 N1 Sn1 133.03(11) . . ?
S1 N1 Sn1 99.25(7) . . ?
C8 C7 C6 119.9(2) . . ?
N1 C1 C3 105.19(14) . . ?
N1 C1 C2 110.15(15) . . ?
C3 C1 C2 110.42(17) . . ?
N1 C1 C4 111.30(14) . . ?
C3 C1 C4 109.41(15) . . ?
C2 C1 C4 110.26(17) . . ?
C10 C9 C8 119.7(2) . . ?
C5 C10 C9 119.0(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 Sn1 S1 N1 -170.78(13) . . . 8_565 ?
Cl1 Sn1 S1 N1 94.61(7) . . . 8_565 ?
N1 Sn1 S1 N1 170.78(13) 8_565 . . . ?
Cl1 Sn1 S1 N1 -94.61(7) . . . . ?
N1 Sn1 S1 C5 -85.39(7) . . . . ?
N1 Sn1 S1 C5 85.39(7) 8_565 . . . ?
Cl1 Sn1 S1 C5 180.0 . . . . ?
N1 S1 C5 C10 49.11(6) 8_565 . . . ?
N1 S1 C5 C10 -49.11(6) . . . . ?
Sn1 S1 C5 C10 0.0 . . . . ?
N1 S1 C5 C6 -130.89(6) 8_565 . . . ?
N1 S1 C5 C6 130.89(6) . . . . ?
Sn1 S1 C5 C6 180.0 . . . . ?
C10 C5 C6 C7 0.0 . . . . ?
S1 C5 C6 C7 180.0 . . . . ?
N1 S1 N1 C1 158.05(9) 8_565 . . . ?
C5 S1 N1 C1 -95.38(14) . . . . ?
Sn1 S1 N1 C1 151.30(15) . . . . ?
N1 S1 N1 Sn1 6.76(10) 8_565 . . . ?
C5 S1 N1 Sn1 113.33(7) . . . . ?
N1 Sn1 N1 C1 -150.33(13) 8_565 . . . ?
Cl1 Sn1 N1 C1 -55.24(14) . . . . ?
S1 Sn1 N1 C1 -144.80(18) . . . . ?
N1 Sn1 N1 S1 -5.53(8) 8_565 . . . ?
Cl1 Sn1 N1 S1 89.56(6) . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
S1 N1 C1 C3 -173.61(12) . . . . ?
Sn1 N1 C1 C3 -34.0(2) . . . . ?
S1 N1 C1 C2 67.39(19) . . . . ?
Sn1 N1 C1 C2 -153.03(14) . . . . ?
S1 N1 C1 C4 -55.22(18) . . . . ?
Sn1 N1 C1 C4 84.35(18) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C6 C5 C10 C9 0.0 . . . . ?
S1 C5 C10 C9 180.0 . . . . ?
C8 C9 C10 C5 0.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_naka214
_database_code_depnum_ccdc_archive 'CCDC 1535388'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C14 H23 Cl Ge N2 S2' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H23 Cl Ge N2 S2'
_chemical_formula_sum            'C14 H23 Cl Ge N2 S2'
_chemical_formula_weight         391.50

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 '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 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   10.9327(8)
_cell_length_b                   12.4204(9)
_cell_length_c                   13.7243(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1863.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8337
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    2.004
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_T_max  0.6783
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9997
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3824
_reflns_number_gt                3708
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0249P)²+1.8472P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(9)
_refine_ls_number_reflns         3824
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
Ge1 Ge 0.14079(3) 0.54785(3) 0.94231(2) 0.02140(9) Uani 1 1 d . . .
S2 S -0.09117(6) 0.60278(6) 0.96808(5) 0.01709(14) Uani 1 1 d . . .
N2 N 0.0143(2) 0.5426(2) 1.03667(16) 0.0184(5) Uani 1 1 d . . .
C5 C -0.2117(2) 0.5070(2) 0.95678(19) 0.0183(6) Uani 1 1 d . . .
C6 C -0.3294(2) 0.5461(3) 0.9738(2) 0.0220(6) Uani 1 1 d . . .
H10 H -0.3425 0.6199 0.9887 0.026 Uiso 1 1 calc R . .
C8 C -0.4056(3) 0.3669(3) 0.9476(2) 0.0302(7) Uani 1 1 d . . .
H12 H -0.4723 0.3178 0.9454 0.036 Uiso 1 1 calc R . .
N1 N -0.0020(2) 0.58458(19) 0.87067(16) 0.0167(5) Uani 1 1 d . . .
C10 C -0.1896(3) 0.3998(2) 0.9338(2) 0.0230(6) Uani 1 1 d . . .
H14 H -0.1088 0.3752 0.9212 0.028 Uiso 1 1 calc R . .
C11 C 0.0171(3) 0.5597(3) 1.1443(2) 0.0232(6) Uani 1 1 d . . .
C2 C 0.0804(3) 0.6211(3) 0.7124(2) 0.0272(7) Uani 1 1 d . . .
H1 H 0.0708 0.5440 0.6990 0.041 Uiso 1 1 calc R . .
H2 H 0.1616 0.6342 0.7402 0.041 Uiso 1 1 calc R . .
H3 H 0.0717 0.6618 0.6516 0.041 Uiso 1 1 calc R . .
C4 C -0.1439(3) 0.6371(3) 0.7413(2) 0.0277(6) Uani 1 1 d . . .
H7 H -0.2065 0.6608 0.7877 0.042 Uiso 1 1 calc R . .
H8 H -0.1542 0.5601 0.7280 0.042 Uiso 1 1 calc R . .
H9 H -0.1525 0.6778 0.6804 0.042 Uiso 1 1 calc R . .
C3 C 0.0000(3) 0.7760(2) 0.8114(2) 0.0285(7) Uani 1 1 d . . .
H4 H 0.0807 0.7861 0.8410 0.043 Uiso 1 1 calc R . .
H5 H -0.0635 0.7975 0.8580 0.043 Uiso 1 1 calc R . .
H6 H -0.0064 0.8204 0.7526 0.043 Uiso 1 1 calc R . .
C7 C -0.4269(3) 0.4745(3) 0.9686(2) 0.0275(7) Uani 1 1 d . . .
H11 H -0.5080 0.4993 0.9794 0.033 Uiso 1 1 calc R . .
C12 C 0.1165(3) 0.4837(3) 1.1813(2) 0.0336(8) Uani 1 1 d . . .
H15 H 0.1945 0.5018 1.1503 0.050 Uiso 1 1 calc R . .
H16 H 0.0944 0.4093 1.1654 0.050 Uiso 1 1 calc R . .
H17 H 0.1243 0.4912 1.2522 0.050 Uiso 1 1 calc R . .
C1 C -0.0171(3) 0.6570(2) 0.7844(2) 0.0192(6) Uani 1 1 d . . .
C14 C -0.1068(3) 0.5284(4) 1.1859(2) 0.0379(9) Uani 1 1 d . . .
H21 H -0.1255 0.4538 1.1678 0.057 Uiso 1 1 calc R . .
H22 H -0.1698 0.5763 1.1596 0.057 Uiso 1 1 calc R . .
H23 H -0.1048 0.5348 1.2570 0.057 Uiso 1 1 calc R . .
C13 C 0.0494(3) 0.6766(3) 1.1698(2) 0.0344(8) Uani 1 1 d . . .
H18 H -0.0132 0.7248 1.1432 0.052 Uiso 1 1 calc R . .
H19 H 0.1292 0.6948 1.1418 0.052 Uiso 1 1 calc R . .
H20 H 0.0527 0.6848 1.2408 0.052 Uiso 1 1 calc R . .
C9 C -0.2875(3) 0.3301(3) 0.9298(2) 0.0278(7) Uani 1 1 d . . .
H13 H -0.2742 0.2563 0.9147 0.033 Uiso 1 1 calc R . .
S1 S 0.28418(8) 0.65656(7) 0.95519(6) 0.03300(19) Uani 1 1 d . . .
Cl1 Cl 0.19273(9) 0.38646(6) 0.90652(6) 0.0389(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
Ge1 N2 1.896(2) . ?
Ge1 N1 1.900(2) . ?
Ge1 S1 2.0764(8) . ?
Ge1 Cl1 2.1406(9) . ?
Ge1 S2 2.6498(8) . ?
S2 N2 1.665(2) . ?
S2 N1 1.670(2) . ?
S2 C5 1.782(3) . ?
N2 C11 1.493(3) . ?
C5 C10 1.390(4) . ?
C5 C6 1.395(4) . ?
C6 C7 1.390(4) . ?
C8 C7 1.388(5) . ?
C8 C9 1.392(5) . ?
N1 C1 1.496(3) . ?
C10 C9 1.378(4) . ?
C11 C14 1.520(4) . ?
C11 C12 1.526(4) . ?
C11 C13 1.535(5) . ?
C2 C1 1.521(4) . ?
C4 C1 1.527(4) . ?
C3 C1 1.536(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
N2 Ge1 N1 76.26(10) . . ?
N2 Ge1 S1 120.99(8) . . ?
N1 Ge1 S1 120.53(8) . . ?
N2 Ge1 Cl1 108.55(8) . . ?
N1 Ge1 Cl1 108.90(8) . . ?
S1 Ge1 Cl1 115.35(4) . . ?
N2 Ge1 S2 38.69(7) . . ?
N1 Ge1 S2 38.85(7) . . ?
S1 Ge1 S2 122.94(3) . . ?
Cl1 Ge1 S2 121.71(3) . . ?
N2 S2 N1 89.29(11) . . ?
N2 S2 C5 105.17(13) . . ?
N1 S2 C5 105.77(12) . . ?
N2 S2 Ge1 45.37(8) . . ?
N1 S2 Ge1 45.53(8) . . ?
C5 S2 Ge1 121.63(10) . . ?
C11 N2 S2 120.68(19) . . ?
C11 N2 Ge1 131.00(18) . . ?
S2 N2 Ge1 95.94(11) . . ?
C10 C5 C6 122.1(3) . . ?
C10 C5 S2 122.0(2) . . ?
C6 C5 S2 115.8(2) . . ?
C7 C6 C5 118.5(3) . . ?
C7 C8 C9 120.6(3) . . ?
C1 N1 S2 119.18(18) . . ?
C1 N1 Ge1 130.16(18) . . ?
S2 N1 Ge1 95.62(11) . . ?
C9 C10 C5 118.4(3) . . ?
N2 C11 C14 108.5(2) . . ?
N2 C11 C12 104.9(2) . . ?
C14 C11 C12 110.6(3) . . ?
N2 C11 C13 111.4(3) . . ?
C14 C11 C13 111.2(3) . . ?
C12 C11 C13 110.2(3) . . ?
C8 C7 C6 119.9(3) . . ?
N1 C1 C2 105.1(2) . . ?
N1 C1 C4 108.1(2) . . ?
C2 C1 C4 109.7(2) . . ?
N1 C1 C3 111.9(2) . . ?
C2 C1 C3 110.7(3) . . ?
C4 C1 C3 111.1(3) . . ?
C10 C9 C8 120.5(3) . . ?

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 Ge1 S2 N2 160.82(17) . . . . ?
S1 Ge1 S2 N2 -99.93(13) . . . . ?
Cl1 Ge1 S2 N2 80.03(13) . . . . ?
N2 Ge1 S2 N1 -160.82(17) . . . . ?
S1 Ge1 S2 N1 99.24(12) . . . . ?
Cl1 Ge1 S2 N1 -80.79(12) . . . . ?
N2 Ge1 S2 C5 -79.86(16) . . . . ?
N1 Ge1 S2 C5 80.96(15) . . . . ?
S1 Ge1 S2 C5 -179.80(11) . . . . ?
Cl1 Ge1 S2 C5 0.17(11) . . . . ?
N1 S2 N2 C11 159.5(2) . . . . ?
C5 S2 N2 C11 -94.3(2) . . . . ?
Ge1 S2 N2 C11 146.0(3) . . . . ?
N1 S2 N2 Ge1 13.56(12) . . . . ?
C5 S2 N2 Ge1 119.72(12) . . . . ?
N1 Ge1 N2 C11 -152.6(3) . . . . ?
S1 Ge1 N2 C11 -35.0(3) . . . . ?
Cl1 Ge1 N2 C11 101.7(3) . . . . ?
S2 Ge1 N2 C11 -140.4(3) . . . . ?
N1 Ge1 N2 S2 -12.25(11) . . . . ?
S1 Ge1 N2 S2 105.35(10) . . . . ?
Cl1 Ge1 N2 S2 -117.89(9) . . . . ?
N2 S2 C5 C10 -46.7(3) . . . . ?
N1 S2 C5 C10 46.9(3) . . . . ?
Ge1 S2 C5 C10 -0.2(3) . . . . ?
N2 S2 C5 C6 132.4(2) . . . . ?
N1 S2 C5 C6 -134.0(2) . . . . ?
Ge1 S2 C5 C6 178.92(17) . . . . ?
C10 C5 C6 C7 0.7(4) . . . . ?
S2 C5 C6 C7 -178.3(2) . . . . ?
N2 S2 N1 C1 -156.4(2) . . . . ?
C5 S2 N1 C1 98.0(2) . . . . ?
Ge1 S2 N1 C1 -142.9(2) . . . . ?
N2 S2 N1 Ge1 -13.52(12) . . . . ?
C5 S2 N1 Ge1 -119.09(12) . . . . ?
N2 Ge1 N1 C1 148.6(2) . . . . ?
S1 Ge1 N1 C1 30.5(3) . . . . ?
Cl1 Ge1 N1 C1 -106.2(2) . . . . ?
S2 Ge1 N1 C1 136.4(3) . . . . ?
N2 Ge1 N1 S2 12.20(11) . . . . ?
S1 Ge1 N1 S2 -105.91(9) . . . . ?
Cl1 Ge1 N1 S2 117.42(9) . . . . ?
C6 C5 C10 C9 -1.2(4) . . . . ?
S2 C5 C10 C9 177.8(2) . . . . ?
S2 N2 C11 C14 56.4(3) . . . . ?
Ge1 N2 C11 C14 -171.1(2) . . . . ?
S2 N2 C11 C12 174.5(2) . . . . ?
Ge1 N2 C11 C12 -53.0(4) . . . . ?
S2 N2 C11 C13 -66.2(3) . . . . ?
Ge1 N2 C11 C13 66.2(3) . . . . ?
C9 C8 C7 C6 -1.3(5) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
S2 N1 C1 C2 177.77(19) . . . . ?
Ge1 N1 C1 C2 49.6(3) . . . . ?
S2 N1 C1 C4 -65.1(3) . . . . ?
Ge1 N1 C1 C4 166.7(2) . . . . ?
S2 N1 C1 C3 57.5(3) . . . . ?
Ge1 N1 C1 C3 -70.6(3) . . . . ?
C5 C10 C9 C8 0.5(5) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.979
_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_naka245
_database_code_depnum_ccdc_archive 'CCDC 1535393'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C21 H38 Cl2 N4 S2 Si3 Sn2' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H38 Cl2 N4 S2 Si3 Sn2'
_chemical_formula_sum            'C21 H38 Cl2 N4 S2 Si3 Sn2'
_chemical_formula_weight         803.22

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'
Si Si 0.0817 0.0704 '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'
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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   10.5769(19)
_cell_length_b                   10.7781(19)
_cell_length_c                   16.372(3)
_cell_angle_alpha                106.544(2)
_cell_angle_beta                 92.127(2)
_cell_angle_gamma                107.936(2)
_cell_volume                     1686.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6388
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    1.888
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6926
_exptl_absorpt_correction_T_max  0.7914
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8756
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6467
_reflns_number_gt                5815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0465P)²+0.0114P] 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         6467
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn2 Sn 0.520963(19) 0.970052(19) 0.862600(12) 0.02080(7) Uani 1 1 d . . .
Sn1 Sn 0.678464(19) 0.909103(19) 0.663708(12) 0.02142(7) Uani 1 1 d . . .
S2 S 0.38115(7) 0.72152(7) 0.69453(5) 0.02039(15) Uani 1 1 d . . .
Cl1 Cl 0.65721(8) 0.67160(8) 0.57190(5) 0.03350(18) Uani 1 1 d . . .
Si3 Si 0.27859(9) 0.42111(8) 0.67982(6) 0.02612(18) Uani 1 1 d . . .
S1 S 0.83207(7) 0.94699(7) 0.85476(5) 0.02122(15) Uani 1 1 d . . .
Si1 Si 0.99175(9) 0.89978(9) 0.71606(6) 0.0296(2) Uani 1 1 d . . .
Si2 Si 0.83670(9) 1.22291(9) 0.92970(6) 0.0323(2) Uani 1 1 d . . .
N3 N 0.5228(2) 0.8360(2) 0.73748(15) 0.0196(5) Uani 1 1 d . . .
N2 N 0.7423(2) 1.0472(2) 0.88042(16) 0.0230(5) Uani 1 1 d . . .
N1 N 0.8387(2) 0.9054(2) 0.75288(16) 0.0227(5) Uani 1 1 d . . .
C13 C 0.3447(3) 0.7484(3) 0.59367(19) 0.0226(6) Uani 1 1 d . . .
C14 C 0.3620(3) 0.8825(3) 0.5939(2) 0.0248(6) Uani 1 1 d . . .
H24 H 0.3934 0.9568 0.6459 0.030 Uiso 1 1 calc R . .
C9 C 0.6943(3) 0.8066(3) 0.9574(2) 0.0300(7) Uani 1 1 d . . .
H14 H 0.7086 0.8948 0.9972 0.036 Uiso 1 1 calc R . .
C4 C 0.7317(3) 0.7940(3) 0.8757(2) 0.0232(6) Uani 1 1 d . . .
N4 N 0.3924(3) 0.5671(2) 0.66301(17) 0.0234(5) Uani 1 1 d . . .
H29 H 0.447(4) 0.561(3) 0.639(2) 0.019(9) Uiso 1 1 d . . .
C15 C 0.3330(3) 0.9061(3) 0.5177(2) 0.0297(7) Uani 1 1 d . . .
H25 H 0.3438 0.9968 0.5174 0.036 Uiso 1 1 calc R . .
C2 C 1.0014(4) 0.9532(4) 0.6177(2) 0.0400(8) Uani 1 1 d . . .
H4 H 0.9974 1.0465 0.6315 0.060 Uiso 1 1 calc R . .
H5 H 0.9260 0.8900 0.5738 0.060 Uiso 1 1 calc R . .
H6 H 1.0860 0.9515 0.5957 0.060 Uiso 1 1 calc R . .
C21 C 0.3545(4) 0.2848(3) 0.6456(2) 0.0354(8) Uani 1 1 d . . .
H36 H 0.4403 0.3119 0.6819 0.053 Uiso 1 1 calc R . .
H37 H 0.3694 0.2710 0.5854 0.053 Uiso 1 1 calc R . .
H38 H 0.2939 0.1992 0.6514 0.053 Uiso 1 1 calc R . .
C17 C 0.2691(4) 0.6645(3) 0.4421(2) 0.0391(8) Uani 1 1 d . . .
H27 H 0.2366 0.5899 0.3903 0.047 Uiso 1 1 calc R . .
C5 C 0.7097(3) 0.6666(3) 0.8163(2) 0.0288(7) Uani 1 1 d . . .
H10 H 0.7346 0.6588 0.7603 0.035 Uiso 1 1 calc R . .
C11 C 0.7304(4) 1.3021(4) 0.9998(2) 0.0383(8) Uani 1 1 d . . .
H18 H 0.7089 1.2580 1.0446 0.057 Uiso 1 1 calc R . .
H19 H 0.6472 1.2897 0.9652 0.057 Uiso 1 1 calc R . .
H20 H 0.7789 1.4003 1.0266 0.057 Uiso 1 1 calc R . .
C7 C 0.6147(4) 0.5617(4) 0.9220(3) 0.0417(9) Uani 1 1 d . . .
H12 H 0.5756 0.4815 0.9380 0.050 Uiso 1 1 calc R . .
C6 C 0.6502(4) 0.5498(3) 0.8401(3) 0.0374(8) Uani 1 1 d . . .
H11 H 0.6337 0.4614 0.8000 0.045 Uiso 1 1 calc R . .
C8 C 0.6361(4) 0.6896(4) 0.9805(2) 0.0391(8) Uani 1 1 d . . .
H13 H 0.6110 0.6973 1.0364 0.047 Uiso 1 1 calc R . .
C18 C 0.2974(4) 0.6398(3) 0.5187(2) 0.0316(7) Uani 1 1 d . . .
H28 H 0.2841 0.5488 0.5192 0.038 Uiso 1 1 calc R . .
C1 C 0.9988(4) 0.7220(4) 0.6885(3) 0.0520(11) Uani 1 1 d . . .
H1 H 0.9227 0.6593 0.6450 0.078 Uiso 1 1 calc R . .
H2 H 0.9946 0.6932 0.7402 0.078 Uiso 1 1 calc R . .
H3 H 1.0828 0.7201 0.6657 0.078 Uiso 1 1 calc R . .
Cl2 Cl 0.51631(8) 1.15721(7) 0.80083(5) 0.03057(17) Uani 1 1 d . . .
C16 C 0.2879(4) 0.7970(3) 0.4410(2) 0.0357(8) Uani 1 1 d . . .
H26 H 0.2703 0.8137 0.3885 0.043 Uiso 1 1 calc R . .
C20 C 0.1131(4) 0.3738(4) 0.6149(3) 0.0408(8) Uani 1 1 d . . .
H33 H 0.1224 0.3474 0.5536 0.061 Uiso 1 1 calc R . .
H34 H 0.0810 0.4525 0.6294 0.061 Uiso 1 1 calc R . .
H35 H 0.0486 0.2965 0.6276 0.061 Uiso 1 1 calc R . .
C10 C 0.8872(4) 1.3083(4) 0.8458(3) 0.0511(10) Uani 1 1 d . . .
H15 H 0.8069 1.3071 0.8133 0.077 Uiso 1 1 calc R . .
H16 H 0.9360 1.2590 0.8066 0.077 Uiso 1 1 calc R . .
H17 H 0.9450 1.4034 0.8735 0.077 Uiso 1 1 calc R . .
C19 C 0.2572(4) 0.4658(4) 0.7950(2) 0.0496(10) Uani 1 1 d . . .
H30 H 0.2192 0.5403 0.8094 0.074 Uiso 1 1 calc R . .
H31 H 0.3446 0.4955 0.8302 0.074 Uiso 1 1 calc R . .
H32 H 0.1966 0.3852 0.8066 0.074 Uiso 1 1 calc R . .
C3 C 1.1348(4) 1.0195(5) 0.7995(3) 0.0558(11) Uani 1 1 d . . .
H7 H 1.1310 0.9895 0.8507 0.084 Uiso 1 1 calc R . .
H8 H 1.1292 1.1123 0.8147 0.084 Uiso 1 1 calc R . .
H9 H 1.2194 1.0199 0.7770 0.084 Uiso 1 1 calc R . .
C12 C 0.9886(5) 1.2392(4) 0.9986(4) 0.0687(15) Uani 1 1 d . . .
H21 H 1.0447 1.1950 0.9631 0.103 Uiso 1 1 calc R . .
H22 H 0.9614 1.1946 1.0427 0.103 Uiso 1 1 calc R . .
H23 H 1.0396 1.3366 1.0265 0.103 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn2 N3 2.149(2) . ?
Sn2 N2 2.207(3) . ?
Sn2 Cl2 2.5126(8) . ?
Sn1 N3 2.164(2) . ?
Sn1 N1 2.213(2) . ?
Sn1 Cl1 2.5083(9) . ?
S2 N3 1.597(2) . ?
S2 N4 1.639(2) . ?
S2 C13 1.804(3) . ?
Si3 N4 1.762(3) . ?
Si3 C21 1.846(3) . ?
Si3 C19 1.850(4) . ?
Si3 C20 1.859(4) . ?
S1 N1 1.609(3) . ?
S1 N2 1.627(2) . ?
S1 C4 1.799(3) . ?
Si1 N1 1.761(3) . ?
Si1 C2 1.855(4) . ?
Si1 C3 1.860(4) . ?
Si1 C1 1.865(4) . ?
Si2 N2 1.772(3) . ?
Si2 C11 1.854(3) . ?
Si2 C12 1.861(4) . ?
Si2 C10 1.868(4) . ?
C13 C18 1.380(4) . ?
C13 C14 1.399(4) . ?
C14 C15 1.384(4) . ?
C9 C8 1.387(5) . ?
C9 C4 1.390(4) . ?
C4 C5 1.382(4) . ?
C15 C16 1.398(5) . ?
C17 C16 1.386(5) . ?
C17 C18 1.394(5) . ?
C5 C6 1.394(5) . ?
C7 C8 1.381(5) . ?
C7 C6 1.387(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
N3 Sn2 N2 89.21(9) . . ?
N3 Sn2 Cl2 91.28(6) . . ?
N2 Sn2 Cl2 90.16(6) . . ?
N3 Sn1 N1 92.99(9) . . ?
N3 Sn1 Cl1 93.37(6) . . ?
N1 Sn1 Cl1 89.86(6) . . ?
N3 S2 N4 111.88(13) . . ?
N3 S2 C13 104.98(13) . . ?
N4 S2 C13 102.20(13) . . ?
N4 Si3 C21 105.47(15) . . ?
N4 Si3 C19 107.79(16) . . ?
C21 Si3 C19 113.50(19) . . ?
N4 Si3 C20 109.87(15) . . ?
C21 Si3 C20 111.50(16) . . ?
C19 Si3 C20 108.58(19) . . ?
N1 S1 N2 110.08(13) . . ?
N1 S1 C4 106.55(14) . . ?
N2 S1 C4 102.59(13) . . ?
N1 Si1 C2 107.57(14) . . ?
N1 Si1 C3 110.17(16) . . ?
C2 Si1 C3 109.6(2) . . ?
N1 Si1 C1 110.64(15) . . ?
C2 Si1 C1 108.90(19) . . ?
C3 Si1 C1 109.9(2) . . ?
N2 Si2 C11 107.51(15) . . ?
N2 Si2 C12 109.80(16) . . ?
C11 Si2 C12 108.2(2) . . ?
N2 Si2 C10 110.09(16) . . ?
C11 Si2 C10 111.33(17) . . ?
C12 Si2 C10 109.9(3) . . ?
S2 N3 Sn2 114.32(12) . . ?
S2 N3 Sn1 123.18(13) . . ?
Sn2 N3 Sn1 118.00(11) . . ?
S1 N2 Si2 114.51(15) . . ?
S1 N2 Sn2 122.97(13) . . ?
Si2 N2 Sn2 122.43(12) . . ?
S1 N1 Si1 118.84(15) . . ?
S1 N1 Sn1 120.28(13) . . ?
Si1 N1 Sn1 118.95(13) . . ?
C18 C13 C14 120.7(3) . . ?
C18 C13 S2 121.2(2) . . ?
C14 C13 S2 118.1(2) . . ?
C15 C14 C13 119.4(3) . . ?
C8 C9 C4 119.5(3) . . ?
C5 C4 C9 121.2(3) . . ?
C5 C4 S1 120.2(2) . . ?
C9 C4 S1 117.9(2) . . ?
S2 N4 Si3 124.83(17) . . ?
C14 C15 C16 120.4(3) . . ?
C16 C17 C18 120.4(3) . . ?
C4 C5 C6 118.6(3) . . ?
C8 C7 C6 120.3(3) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C8 C9 119.8(3) . . ?
C13 C18 C17 119.6(3) . . ?
C17 C16 C15 119.5(3) . . ?

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
N4 S2 N3 Sn2 -127.47(14) . . . . ?
C13 S2 N3 Sn2 122.46(13) . . . . ?
N4 S2 N3 Sn1 76.87(17) . . . . ?
C13 S2 N3 Sn1 -33.20(17) . . . . ?
N2 Sn2 N3 S2 167.80(13) . . . . ?
Cl2 Sn2 N3 S2 -102.06(12) . . . . ?
N2 Sn2 N3 Sn1 -35.20(12) . . . . ?
Cl2 Sn2 N3 Sn1 54.94(10) . . . . ?
N1 Sn1 N3 S2 -136.99(15) . . . . ?
Cl1 Sn1 N3 S2 -46.95(14) . . . . ?
N1 Sn1 N3 Sn2 68.19(12) . . . . ?
Cl1 Sn1 N3 Sn2 158.23(10) . . . . ?
N1 S1 N2 Si2 -103.26(16) . . . . ?
C4 S1 N2 Si2 143.63(16) . . . . ?
N1 S1 N2 Sn2 80.17(18) . . . . ?
C4 S1 N2 Sn2 -32.94(18) . . . . ?
C11 Si2 N2 S1 -152.47(17) . . . . ?
C12 Si2 N2 S1 -35.0(3) . . . . ?
C10 Si2 N2 S1 86.1(2) . . . . ?
C11 Si2 N2 Sn2 24.1(2) . . . . ?
C12 Si2 N2 Sn2 141.6(2) . . . . ?
C10 Si2 N2 Sn2 -97.3(2) . . . . ?
N3 Sn2 N2 S1 -43.95(16) . . . . ?
Cl2 Sn2 N2 S1 -135.23(15) . . . . ?
N3 Sn2 N2 Si2 139.75(15) . . . . ?
Cl2 Sn2 N2 Si2 48.47(14) . . . . ?
N2 S1 N1 Si1 139.48(15) . . . . ?
C4 S1 N1 Si1 -109.98(16) . . . . ?
N2 S1 N1 Sn1 -24.53(19) . . . . ?
C4 S1 N1 Sn1 86.01(16) . . . . ?
C2 Si1 N1 S1 -146.58(18) . . . . ?
C3 Si1 N1 S1 -27.2(2) . . . . ?
C1 Si1 N1 S1 94.6(2) . . . . ?
C2 Si1 N1 Sn1 17.65(19) . . . . ?
C3 Si1 N1 Sn1 137.07(19) . . . . ?
C1 Si1 N1 Sn1 -101.2(2) . . . . ?
N3 Sn1 N1 S1 -36.83(15) . . . . ?
Cl1 Sn1 N1 S1 -130.20(14) . . . . ?
N3 Sn1 N1 Si1 159.17(14) . . . . ?
Cl1 Sn1 N1 Si1 65.80(13) . . . . ?
N3 S2 C13 C18 134.9(3) . . . . ?
N4 S2 C13 C18 18.0(3) . . . . ?
N3 S2 C13 C14 -46.9(3) . . . . ?
N4 S2 C13 C14 -163.8(2) . . . . ?
C18 C13 C14 C15 -0.9(5) . . . . ?
S2 C13 C14 C15 -179.1(2) . . . . ?
C8 C9 C4 C5 1.2(5) . . . . ?
C8 C9 C4 S1 -169.6(3) . . . . ?
N1 S1 C4 C5 18.2(3) . . . . ?
N2 S1 C4 C5 133.8(2) . . . . ?
N1 S1 C4 C9 -170.9(2) . . . . ?
N2 S1 C4 C9 -55.2(3) . . . . ?
N3 S2 N4 Si3 135.70(18) . . . . ?
C13 S2 N4 Si3 -112.48(19) . . . . ?
C21 Si3 N4 S2 -171.91(19) . . . . ?
C19 Si3 N4 S2 -50.4(3) . . . . ?
C20 Si3 N4 S2 67.8(2) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C9 C4 C5 C6 -0.8(4) . . . . ?
S1 C4 C5 C6 169.9(2) . . . . ?
C8 C7 C6 C5 1.1(5) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C4 C9 C8 C7 -0.6(5) . . . . ?
C14 C13 C18 C17 1.3(5) . . . . ?
S2 C13 C18 C17 179.4(3) . . . . ?
C16 C17 C18 C13 -0.2(6) . . . . ?
C18 C17 C16 C15 -1.3(6) . . . . ?
C14 C15 C16 C17 1.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         1.018
_refine_diff_density_min         -1.078
_refine_diff_density_rms         0.109
####################################################################### 
# 
# 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_naka284
_database_code_depnum_ccdc_archive 'CCDC 1535390'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C28 H46 Cl2 N4 S4 Sn2, C6 H6' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H46 Cl2 N4 S4 Sn2, C6 H6'
_chemical_formula_sum            'C34 H52 Cl2 N4 S4 Sn2'
_chemical_formula_weight         953.32

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   12.9068(10)
_cell_length_b                   11.6435(9)
_cell_length_c                   14.1347(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.8210(10)
_cell_angle_gamma                90.00
_cell_volume                     2113.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6847
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964
_exptl_absorpt_coefficient_mu    1.534
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_T_max  0.9554
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10211
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3907
_reflns_number_gt                3507
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0578P)²+2.6698P] 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         3907
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.632060(17) 0.022644(19) 0.010869(14) 0.01612(10) Uani 1 1 d . . .
S2 S 0.77566(6) 0.21438(7) 0.00353(5) 0.01462(18) Uani 1 1 d . . .
N1 N 0.7182(2) 0.1530(2) 0.08912(18) 0.0163(6) Uani 1 1 d . . .
C15 C 0.9662(3) 0.5941(4) -0.0571(3) 0.0346(9) Uani 1 1 d . . .
H24 H 0.9433 0.6577 -0.0958 0.042 Uiso 1 1 calc R . .
N2 N 0.7376(2) 0.1148(2) -0.07325(18) 0.0165(6) Uani 1 1 d . . .
C5 C 0.6975(3) 0.3376(3) -0.0343(2) 0.0148(6) Uani 1 1 d . . .
C13 C 0.9134(3) 0.0458(4) -0.1063(3) 0.0346(9) Uani 1 1 d . . .
H18 H 0.9463 0.1055 -0.0646 0.052 Uiso 1 1 calc R . .
H19 H 0.9570 0.0297 -0.1576 0.052 Uiso 1 1 calc R . .
H20 H 0.9055 -0.0244 -0.0693 0.052 Uiso 1 1 calc R . .
C11 C 0.8061(3) 0.0871(3) -0.1488(2) 0.0202(7) Uani 1 1 d . . .
C1 C 0.7288(3) 0.1992(3) 0.1886(2) 0.0174(7) Uani 1 1 d . . .
C6 C 0.7400(3) 0.4445(3) -0.0107(2) 0.0190(7) Uani 1 1 d . . .
H10 H 0.8079 0.4508 0.0218 0.023 Uiso 1 1 calc R . .
C10 C 0.5994(3) 0.3271(3) -0.0845(2) 0.0209(7) Uani 1 1 d . . .
H14 H 0.5717 0.2536 -0.1018 0.025 Uiso 1 1 calc R . .
C2 C 0.6369(3) 0.2774(3) 0.2043(2) 0.0250(8) Uani 1 1 d . . .
H1 H 0.6382 0.3451 0.1633 0.038 Uiso 1 1 calc R . .
H2 H 0.6420 0.3016 0.2710 0.038 Uiso 1 1 calc R . .
H3 H 0.5716 0.2355 0.1886 0.038 Uiso 1 1 calc R . .
C16 C 0.9920(3) 0.4904(4) -0.0974(3) 0.0341(10) Uani 1 1 d . . .
H25 H 0.9866 0.4836 -0.1647 0.041 Uiso 1 1 calc R . .
C4 C 0.7312(3) 0.0941(3) 0.2549(2) 0.0232(8) Uani 1 1 d . . .
H7 H 0.6657 0.0514 0.2427 0.035 Uiso 1 1 calc R . .
H8 H 0.7397 0.1198 0.3212 0.035 Uiso 1 1 calc R . .
H9 H 0.7895 0.0442 0.2428 0.035 Uiso 1 1 calc R . .
C17 C 1.0251(3) 0.3978(4) -0.0428(3) 0.0332(9) Uani 1 1 d . . .
H26 H 1.0423 0.3279 -0.0723 0.040 Uiso 1 1 calc R . .
C7 C 0.6812(3) 0.5429(3) -0.0353(3) 0.0233(8) Uani 1 1 d . . .
H11 H 0.7086 0.6167 -0.0186 0.028 Uiso 1 1 calc R . .
C14 C 0.7507(3) -0.0088(3) -0.2086(3) 0.0239(8) Uani 1 1 d . . .
H21 H 0.7414 -0.0756 -0.1681 0.036 Uiso 1 1 calc R . .
H22 H 0.7928 -0.0308 -0.2597 0.036 Uiso 1 1 calc R . .
H23 H 0.6825 0.0185 -0.2363 0.036 Uiso 1 1 calc R . .
C9 C 0.5433(3) 0.4250(3) -0.1087(2) 0.0249(8) Uani 1 1 d . . .
H13 H 0.4762 0.4190 -0.1429 0.030 Uiso 1 1 calc R . .
C8 C 0.5839(3) 0.5328(3) -0.0837(3) 0.0247(8) Uani 1 1 d . . .
H12 H 0.5441 0.5998 -0.1002 0.030 Uiso 1 1 calc R . .
C3 C 0.8313(3) 0.2645(3) 0.2089(2) 0.0231(8) Uani 1 1 d . . .
H4 H 0.8892 0.2153 0.1941 0.035 Uiso 1 1 calc R . .
H5 H 0.8410 0.2862 0.2762 0.035 Uiso 1 1 calc R . .
H6 H 0.8296 0.3338 0.1695 0.035 Uiso 1 1 calc R . .
C12 C 0.8177(3) 0.1936(3) -0.2097(3) 0.0317(9) Uani 1 1 d . . .
H15 H 0.7488 0.2191 -0.2373 0.048 Uiso 1 1 calc R . .
H16 H 0.8608 0.1752 -0.2609 0.048 Uiso 1 1 calc R . .
H17 H 0.8509 0.2551 -0.1701 0.048 Uiso 1 1 calc R . .
S1 S 0.50088(8) -0.00741(8) 0.12222(6) 0.0246(2) Uani 1 1 d . . .
Cl1 Cl 0.73144(8) -0.14834(7) 0.03433(6) 0.0303(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
Sn1 N1 2.125(3) . ?
Sn1 N2 2.179(3) . ?
Sn1 Cl1 2.3732(9) . ?
Sn1 S1 2.4207(9) 3_655 ?
Sn1 S1 2.4509(9) . ?
Sn1 S2 2.9102(8) . ?
S2 N2 1.630(3) . ?
S2 N1 1.645(3) . ?
S2 C5 1.803(3) . ?
N1 C1 1.499(4) . ?
C15 C16 1.390(6) . ?
C15 C17 1.408(6) 3_765 ?
N2 C11 1.490(4) . ?
C5 C6 1.387(5) . ?
C5 C10 1.393(5) . ?
C13 C11 1.530(5) . ?
C11 C12 1.526(5) . ?
C11 C14 1.534(5) . ?
C1 C3 1.527(5) . ?
C1 C2 1.529(5) . ?
C1 C4 1.539(5) . ?
C6 C7 1.399(5) . ?
C10 C9 1.374(5) . ?
C16 C17 1.369(6) . ?
C17 C15 1.408(6) 3_765 ?
C7 C8 1.372(5) . ?
C9 C8 1.393(6) . ?
S1 Sn1 2.4207(9) 3_655 ?

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 Sn1 N2 66.99(10) . . ?
N1 Sn1 Cl1 106.25(8) . . ?
N2 Sn1 Cl1 97.49(8) . . ?
N1 Sn1 S1 138.52(8) . 3_655 ?
N2 Sn1 S1 92.59(7) . 3_655 ?
Cl1 Sn1 S1 112.18(3) . 3_655 ?
N1 Sn1 S1 97.29(8) . . ?
N2 Sn1 S1 158.66(8) . . ?
Cl1 Sn1 S1 100.91(3) . . ?
S1 Sn1 S1 90.41(3) 3_655 . ?
N1 Sn1 S2 33.79(7) . . ?
N2 Sn1 S2 33.62(7) . . ?
Cl1 Sn1 S2 108.14(3) . . ?
S1 Sn1 S2 115.62(3) 3_655 . ?
S1 Sn1 S2 128.05(3) . . ?
N2 S2 N1 93.03(13) . . ?
N2 S2 C5 104.29(14) . . ?
N1 S2 C5 106.46(14) . . ?
N2 S2 Sn1 47.77(9) . . ?
N1 S2 Sn1 45.92(9) . . ?
C5 S2 Sn1 106.37(11) . . ?
C1 N1 S2 121.9(2) . . ?
C1 N1 Sn1 137.6(2) . . ?
S2 N1 Sn1 100.29(12) . . ?
C16 C15 C17 118.1(4) . 3_765 ?
C11 N2 S2 118.1(2) . . ?
C11 N2 Sn1 137.2(2) . . ?
S2 N2 Sn1 98.62(12) . . ?
C6 C5 C10 121.2(3) . . ?
C6 C5 S2 116.6(2) . . ?
C10 C5 S2 122.3(3) . . ?
N2 C11 C12 109.1(3) . . ?
N2 C11 C13 111.4(3) . . ?
C12 C11 C13 110.0(3) . . ?
N2 C11 C14 106.0(3) . . ?
C12 C11 C14 110.4(3) . . ?
C13 C11 C14 109.9(3) . . ?
N1 C1 C3 110.5(3) . . ?
N1 C1 C2 110.5(3) . . ?
C3 C1 C2 110.3(3) . . ?
N1 C1 C4 106.3(3) . . ?
C3 C1 C4 108.5(3) . . ?
C2 C1 C4 110.6(3) . . ?
C5 C6 C7 118.9(3) . . ?
C9 C10 C5 118.9(3) . . ?
C17 C16 C15 121.9(4) . . ?
C16 C17 C15 120.0(4) . 3_765 ?
C8 C7 C6 120.0(3) . . ?
C10 C9 C8 120.6(3) . . ?
C7 C8 C9 120.4(3) . . ?
Sn1 S1 Sn1 89.59(3) 3_655 . ?

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 Sn1 S2 N2 168.1(2) . . . . ?
Cl1 Sn1 S2 N2 75.82(14) . . . . ?
S1 Sn1 S2 N2 -50.89(14) 3_655 . . . ?
S1 Sn1 S2 N2 -163.56(14) . . . . ?
N2 Sn1 S2 N1 -168.1(2) . . . . ?
Cl1 Sn1 S2 N1 -92.27(14) . . . . ?
S1 Sn1 S2 N1 141.02(14) 3_655 . . . ?
S1 Sn1 S2 N1 28.35(14) . . . . ?
N1 Sn1 S2 C5 -97.28(17) . . . . ?
N2 Sn1 S2 C5 94.64(17) . . . . ?
Cl1 Sn1 S2 C5 170.45(10) . . . . ?
S1 Sn1 S2 C5 43.74(11) 3_655 . . . ?
S1 Sn1 S2 C5 -68.93(11) . . . . ?
N2 S2 N1 C1 175.6(3) . . . . ?
C5 S2 N1 C1 -78.5(3) . . . . ?
Sn1 S2 N1 C1 -175.6(3) . . . . ?
N2 S2 N1 Sn1 -8.80(14) . . . . ?
C5 S2 N1 Sn1 97.07(15) . . . . ?
N2 Sn1 N1 C1 -178.4(3) . . . . ?
Cl1 Sn1 N1 C1 -87.0(3) . . . . ?
S1 Sn1 N1 C1 115.6(3) 3_655 . . . ?
S1 Sn1 N1 C1 16.6(3) . . . . ?
S2 Sn1 N1 C1 174.5(4) . . . . ?
N2 Sn1 N1 S2 7.13(12) . . . . ?
Cl1 Sn1 N1 S2 98.50(12) . . . . ?
S1 Sn1 N1 S2 -58.90(18) 3_655 . . . ?
S1 Sn1 N1 S2 -157.86(11) . . . . ?
N1 S2 N2 C11 -148.8(2) . . . . ?
C5 S2 N2 C11 103.4(3) . . . . ?
Sn1 S2 N2 C11 -157.3(3) . . . . ?
N1 S2 N2 Sn1 8.54(14) . . . . ?
C5 S2 N2 Sn1 -99.30(14) . . . . ?
N1 Sn1 N2 C11 142.7(3) . . . . ?
Cl1 Sn1 N2 C11 38.2(3) . . . . ?
S1 Sn1 N2 C11 -74.6(3) 3_655 . . . ?
S1 Sn1 N2 C11 -172.3(2) . . . . ?
S2 Sn1 N2 C11 149.9(4) . . . . ?
N1 Sn1 N2 S2 -7.16(12) . . . . ?
Cl1 Sn1 N2 S2 -111.68(11) . . . . ?
S1 Sn1 N2 S2 135.54(11) 3_655 . . . ?
S1 Sn1 N2 S2 37.8(3) . . . . ?
N2 S2 C5 C6 -153.2(2) . . . . ?
N1 S2 C5 C6 109.2(3) . . . . ?
Sn1 S2 C5 C6 157.2(2) . . . . ?
N2 S2 C5 C10 26.9(3) . . . . ?
N1 S2 C5 C10 -70.7(3) . . . . ?
Sn1 S2 C5 C10 -22.7(3) . . . . ?
S2 N2 C11 C12 -61.6(3) . . . . ?
Sn1 N2 C11 C12 152.6(3) . . . . ?
S2 N2 C11 C13 60.1(4) . . . . ?
Sn1 N2 C11 C13 -85.7(4) . . . . ?
S2 N2 C11 C14 179.6(2) . . . . ?
Sn1 N2 C11 C14 33.8(4) . . . . ?
S2 N1 C1 C3 -26.8(4) . . . . ?
Sn1 N1 C1 C3 159.6(3) . . . . ?
S2 N1 C1 C2 95.5(3) . . . . ?
Sn1 N1 C1 C2 -78.0(4) . . . . ?
S2 N1 C1 C4 -144.4(2) . . . . ?
Sn1 N1 C1 C4 42.1(4) . . . . ?
C10 C5 C6 C7 2.1(5) . . . . ?
S2 C5 C6 C7 -177.8(3) . . . . ?
C6 C5 C10 C9 -1.6(5) . . . . ?
S2 C5 C10 C9 178.3(3) . . . . ?
C17 C15 C16 C17 0.0(6) 3_765 . . . ?
C15 C16 C17 C15 0.0(6) . . . 3_765 ?
C5 C6 C7 C8 -1.2(5) . . . . ?
C5 C10 C9 C8 0.2(5) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C10 C9 C8 C7 0.7(5) . . . . ?
N1 Sn1 S1 Sn1 139.13(8) . . . 3_655 ?
N2 Sn1 S1 Sn1 98.2(2) . . . 3_655 ?
Cl1 Sn1 S1 Sn1 -112.70(3) . . . 3_655 ?
S1 Sn1 S1 Sn1 0.0 3_655 . . 3_655 ?
S2 Sn1 S1 Sn1 123.69(3) . . . 3_655 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         3.371
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_naka215
_database_code_depnum_ccdc_archive 'CCDC 1535389'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C14 H23 Cl Ge N2 S Se' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H23 Cl Ge N2 S Se'
_chemical_formula_sum            'C14 H23 Cl Ge N2 S Se'
_chemical_formula_weight         438.40

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   17.7011(14)
_cell_length_b                   11.7652(9)
_cell_length_c                   18.2391(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.3550(10)
_cell_angle_gamma                90.00
_cell_volume                     3747.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    3.824
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_T_max  0.7247
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19730
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         26.50
_reflns_number_total             7714
_reflns_number_gt                6455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0157P)²+0.0012P] 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         7714
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.004
_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
Ge1 Ge 0.387339(11) -0.363911(17) 1.161416(12) 0.01708(6) Uani 1 1 d . . .
Se2 Se 0.320286(11) 0.119707(17) 1.020185(12) 0.02157(6) Uani 1 1 d . . .
Ge2 Ge 0.244166(11) 0.222184(17) 0.938747(12) 0.01518(5) Uani 1 1 d . . .
Se1 Se 0.483004(12) -0.358619(19) 1.254625(13) 0.02949(6) Uani 1 1 d . . .
S1 S 0.30972(3) -0.20264(4) 1.07903(3) 0.01553(11) Uani 1 1 d . . .
Cl1 Cl 0.34563(3) -0.53422(4) 1.13006(3) 0.02362(12) Uani 1 1 d . . .
S2 S 0.11787(3) 0.15389(4) 0.84908(3) 0.01642(11) Uani 1 1 d . . .
Cl2 Cl 0.27526(3) 0.39930(4) 0.92976(3) 0.02484(12) Uani 1 1 d . . .
C19 C 0.06053(10) 0.25253(16) 0.79014(11) 0.0155(4) Uani 1 1 d . . .
N4 N 0.13535(8) 0.21845(14) 0.93131(9) 0.0170(4) Uani 1 1 d . . .
N3 N 0.20811(8) 0.17872(14) 0.83901(9) 0.0176(4) Uani 1 1 d . . .
N1 N 0.29648(9) -0.27432(13) 1.15438(9) 0.0162(4) Uani 1 1 d . . .
N2 N 0.38274(8) -0.28729(13) 1.06849(9) 0.0167(4) Uani 1 1 d . . .
C6 C 0.20506(11) -0.35617(17) 1.00448(12) 0.0226(5) Uani 1 1 d . . .
H10 H 0.2276 -0.4126 1.0385 0.027 Uiso 1 1 calc R . .
C7 C 0.14422(11) -0.38269(18) 0.94931(12) 0.0234(5) Uani 1 1 d . . .
H11 H 0.1248 -0.4581 0.9450 0.028 Uiso 1 1 calc R . .
C22 C -0.03509(11) 0.39582(17) 0.70047(12) 0.0212(5) Uani 1 1 d . . .
H35 H -0.0685 0.4457 0.6696 0.025 Uiso 1 1 calc R . .
C5 C 0.23237(10) -0.24580(16) 1.00908(11) 0.0160(4) Uani 1 1 d . . .
C20 C 0.07366(11) 0.36843(17) 0.79609(11) 0.0204(5) Uani 1 1 d . . .
H33 H 0.1154 0.3977 0.8303 0.024 Uiso 1 1 calc R . .
C11 C 0.44565(11) -0.24175(18) 1.03139(11) 0.0200(5) Uani 1 1 d . . .
C23 C -0.04661(11) 0.28014(17) 0.69437(11) 0.0200(5) Uani 1 1 d . . .
H36 H -0.0871 0.2507 0.6589 0.024 Uiso 1 1 calc R . .
C25 C 0.08526(11) 0.19909(18) 0.98840(12) 0.0205(5) Uani 1 1 d . . .
C24 C 0.00089(11) 0.20671(17) 0.74005(11) 0.0179(4) Uani 1 1 d . . .
H37 H -0.0072 0.1269 0.7371 0.021 Uiso 1 1 calc R . .
C21 C 0.02471(11) 0.44059(18) 0.75118(12) 0.0232(5) Uani 1 1 d . . .
H34 H 0.0319 0.5205 0.7549 0.028 Uiso 1 1 calc R . .
C15 C 0.24543(11) 0.12062(17) 0.78199(11) 0.0192(5) Uani 1 1 d . . .
C1 C 0.26275(11) -0.21415(16) 1.21349(11) 0.0178(4) Uani 1 1 d . . .
C2 C 0.25244(12) -0.30457(17) 1.27098(12) 0.0239(5) Uani 1 1 d . . .
H1 H 0.2174 -0.3635 1.2477 0.036 Uiso 1 1 calc R . .
H2 H 0.2311 -0.2695 1.3119 0.036 Uiso 1 1 calc R . .
H3 H 0.3022 -0.3388 1.2903 0.036 Uiso 1 1 calc R . .
C4 C 0.31608(11) -0.11928(17) 1.24878(12) 0.0244(5) Uani 1 1 d . . .
H7 H 0.3664 -0.1514 1.2684 0.037 Uiso 1 1 calc R . .
H8 H 0.2943 -0.0841 1.2893 0.037 Uiso 1 1 calc R . .
H9 H 0.3216 -0.0618 1.2112 0.037 Uiso 1 1 calc R . .
C10 C 0.20027(11) -0.16153(18) 0.96030(11) 0.0196(5) Uani 1 1 d . . .
H14 H 0.2196 -0.0861 0.9644 0.023 Uiso 1 1 calc R . .
C17 C 0.20198(12) 0.14817(19) 0.70486(12) 0.0265(5) Uani 1 1 d . . .
H27 H 0.1517 0.1112 0.6981 0.040 Uiso 1 1 calc R . .
H28 H 0.2311 0.1205 0.6671 0.040 Uiso 1 1 calc R . .
H29 H 0.1952 0.2306 0.6998 0.040 Uiso 1 1 calc R . .
C26 C 0.10875(12) 0.28942(19) 1.04759(12) 0.0304(5) Uani 1 1 d . . .
H38 H 0.1632 0.2807 1.0679 0.046 Uiso 1 1 calc R . .
H39 H 0.0783 0.2806 1.0875 0.046 Uiso 1 1 calc R . .
H40 H 0.0999 0.3651 1.0254 0.046 Uiso 1 1 calc R . .
C8 C 0.11170(11) -0.29961(18) 0.90051(11) 0.0209(5) Uani 1 1 d . . .
H12 H 0.0697 -0.3183 0.8630 0.025 Uiso 1 1 calc R . .
C9 C 0.13947(11) -0.19030(18) 0.90566(12) 0.0226(5) Uani 1 1 d . . .
H13 H 0.1168 -0.1342 0.8715 0.027 Uiso 1 1 calc R . .
C13 C 0.48473(12) -0.14044(18) 1.07404(13) 0.0279(5) Uani 1 1 d . . .
H18 H 0.4485 -0.0771 1.0718 0.042 Uiso 1 1 calc R . .
H19 H 0.5290 -0.1172 1.0517 0.042 Uiso 1 1 calc R . .
H20 H 0.5018 -0.1620 1.1260 0.042 Uiso 1 1 calc R . .
C3 C 0.18499(11) -0.16518(19) 1.17920(12) 0.0260(5) Uani 1 1 d . . .
H4 H 0.1922 -0.1077 1.1421 0.039 Uiso 1 1 calc R . .
H5 H 0.1607 -0.1302 1.2182 0.039 Uiso 1 1 calc R . .
H6 H 0.1522 -0.2263 1.1553 0.039 Uiso 1 1 calc R . .
C28 C 0.00153(11) 0.21545(19) 0.95278(12) 0.0282(5) Uani 1 1 d . . .
H44 H -0.0051 0.2914 0.9305 0.042 Uiso 1 1 calc R . .
H45 H -0.0314 0.2076 0.9908 0.042 Uiso 1 1 calc R . .
H46 H -0.0125 0.1578 0.9142 0.042 Uiso 1 1 calc R . .
C16 C 0.32545(11) 0.1718(2) 0.79059(13) 0.0292(5) Uani 1 1 d . . .
H24 H 0.3216 0.2543 0.7840 0.044 Uiso 1 1 calc R . .
H25 H 0.3530 0.1393 0.7530 0.044 Uiso 1 1 calc R . .
H26 H 0.3533 0.1546 0.8403 0.044 Uiso 1 1 calc R . .
C14 C 0.41243(12) -0.2049(2) 0.95266(12) 0.0338(6) Uani 1 1 d . . .
H21 H 0.3863 -0.2694 0.9255 0.051 Uiso 1 1 calc R . .
H22 H 0.4538 -0.1785 0.9272 0.051 Uiso 1 1 calc R . .
H23 H 0.3758 -0.1430 0.9546 0.051 Uiso 1 1 calc R . .
C12 C 0.50170(12) -0.33963(19) 1.03008(15) 0.0372(6) Uani 1 1 d . . .
H15 H 0.5215 -0.3632 1.0811 0.056 Uiso 1 1 calc R . .
H16 H 0.5442 -0.3149 1.0056 0.056 Uiso 1 1 calc R . .
H17 H 0.4754 -0.4038 1.0027 0.056 Uiso 1 1 calc R . .
C18 C 0.24989(14) -0.00737(19) 0.79444(14) 0.0371(6) Uani 1 1 d . . .
H30 H 0.2762 -0.0232 0.8449 0.056 Uiso 1 1 calc R . .
H31 H 0.2783 -0.0422 0.7584 0.056 Uiso 1 1 calc R . .
H32 H 0.1980 -0.0391 0.7880 0.056 Uiso 1 1 calc R . .
C27 C 0.09695(12) 0.08087(19) 1.02282(13) 0.0289(5) Uani 1 1 d . . .
H41 H 0.0819 0.0233 0.9844 0.043 Uiso 1 1 calc R . .
H42 H 0.0654 0.0728 1.0620 0.043 Uiso 1 1 calc R . .
H43 H 0.1510 0.0707 1.0442 0.043 Uiso 1 1 calc R . .


_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
Ge1 N2 1.9097(16) . ?
Ge1 N1 1.9097(15) . ?
Ge1 Cl1 2.1794(5) . ?
Ge1 Se1 2.1967(3) . ?
Ge1 S1 2.6598(5) . ?
Se2 Ge2 2.1965(3) . ?
Ge2 N3 1.8976(16) . ?
Ge2 N4 1.9094(15) . ?
Ge2 Cl2 2.1682(6) . ?
Ge2 S2 2.6701(5) . ?
S1 N1 1.6611(17) . ?
S1 N2 1.6674(16) . ?
S1 C5 1.7867(19) . ?
S2 N3 1.6631(16) . ?
S2 N4 1.6647(16) . ?
S2 C19 1.7825(19) . ?
C19 C20 1.385(3) . ?
C19 C24 1.388(3) . ?
N4 C25 1.491(2) . ?
N3 C15 1.486(2) . ?
N1 C1 1.493(2) . ?
N2 C11 1.493(3) . ?
C6 C5 1.383(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.383(3) . ?
C22 C23 1.378(3) . ?
C22 C21 1.391(3) . ?
C5 C10 1.390(3) . ?
C20 C21 1.383(3) . ?
C11 C12 1.523(3) . ?
C11 C14 1.524(3) . ?
C11 C13 1.526(3) . ?
C23 C24 1.386(3) . ?
C25 C26 1.524(3) . ?
C25 C27 1.526(3) . ?
C25 C28 1.531(3) . ?
C15 C18 1.523(3) . ?
C15 C16 1.523(3) . ?
C15 C17 1.524(3) . ?
C1 C2 1.525(3) . ?
C1 C3 1.529(3) . ?
C1 C4 1.534(3) . ?
C10 C9 1.385(3) . ?
C8 C9 1.375(3) . ?

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
N2 Ge1 N1 76.46(7) . . ?
N2 Ge1 Cl1 103.73(5) . . ?
N1 Ge1 Cl1 104.13(5) . . ?
N2 Ge1 Se1 126.14(5) . . ?
N1 Ge1 Se1 124.83(5) . . ?
Cl1 Ge1 Se1 114.505(17) . . ?
N2 Ge1 S1 38.58(5) . . ?
N1 Ge1 S1 38.39(5) . . ?
Cl1 Ge1 S1 112.691(18) . . ?
Se1 Ge1 S1 132.798(15) . . ?
N3 Ge2 N4 75.37(7) . . ?
N3 Ge2 Cl2 103.68(5) . . ?
N4 Ge2 Cl2 106.40(5) . . ?
N3 Ge2 Se2 125.04(5) . . ?
N4 Ge2 Se2 122.43(5) . . ?
Cl2 Ge2 Se2 116.315(17) . . ?
N3 Ge2 S2 38.19(5) . . ?
N4 Ge2 S2 38.28(5) . . ?
Cl2 Ge2 S2 116.129(19) . . ?
Se2 Ge2 S2 127.555(15) . . ?
N1 S1 N2 90.48(8) . . ?
N1 S1 C5 104.58(9) . . ?
N2 S1 C5 105.45(9) . . ?
N1 S1 Ge1 45.56(5) . . ?
N2 S1 Ge1 45.58(6) . . ?
C5 S1 Ge1 117.79(7) . . ?
N3 S2 N4 88.75(8) . . ?
N3 S2 C19 106.38(9) . . ?
N4 S2 C19 104.51(9) . . ?
N3 S2 Ge2 44.87(6) . . ?
N4 S2 Ge2 45.28(5) . . ?
C19 S2 Ge2 120.76(7) . . ?
C20 C19 C24 122.29(17) . . ?
C20 C19 S2 121.46(14) . . ?
C24 C19 S2 116.21(15) . . ?
C25 N4 S2 121.00(13) . . ?
C25 N4 Ge2 131.42(12) . . ?
S2 N4 Ge2 96.44(8) . . ?
C15 N3 S2 122.74(13) . . ?
C15 N3 Ge2 132.55(12) . . ?
S2 N3 Ge2 96.94(8) . . ?
C1 N1 S1 118.91(12) . . ?
C1 N1 Ge1 130.12(12) . . ?
S1 N1 Ge1 96.05(8) . . ?
C11 N2 S1 119.15(13) . . ?
C11 N2 Ge1 130.10(12) . . ?
S1 N2 Ge1 95.83(8) . . ?
C5 C6 C7 118.58(18) . . ?
C8 C7 C6 120.11(19) . . ?
C23 C22 C21 120.95(18) . . ?
C6 C5 C10 121.88(18) . . ?
C6 C5 S1 121.98(15) . . ?
C10 C5 S1 116.13(15) . . ?
C21 C20 C19 118.50(18) . . ?
N2 C11 C12 105.76(17) . . ?
N2 C11 C14 109.10(16) . . ?
C12 C11 C14 110.68(19) . . ?
N2 C11 C13 111.03(17) . . ?
C12 C11 C13 110.86(17) . . ?
C14 C11 C13 109.35(18) . . ?
C22 C23 C24 119.99(18) . . ?
N4 C25 C26 105.28(16) . . ?
N4 C25 C27 111.73(17) . . ?
C26 C25 C27 109.94(18) . . ?
N4 C25 C28 109.21(16) . . ?
C26 C25 C28 110.30(18) . . ?
C27 C25 C28 110.27(17) . . ?
C23 C24 C19 118.42(19) . . ?
C20 C21 C22 119.82(19) . . ?
N3 C15 C18 111.63(17) . . ?
N3 C15 C16 104.95(16) . . ?
C18 C15 C16 110.52(17) . . ?
N3 C15 C17 109.44(16) . . ?
C18 C15 C17 110.73(18) . . ?
C16 C15 C17 109.41(18) . . ?
N1 C1 C2 105.80(15) . . ?
N1 C1 C3 108.81(16) . . ?
C2 C1 C3 110.10(17) . . ?
N1 C1 C4 110.90(16) . . ?
C2 C1 C4 110.68(17) . . ?
C3 C1 C4 110.43(17) . . ?
C9 C10 C5 118.38(19) . . ?
C9 C8 C7 120.70(19) . . ?
C8 C9 C10 120.35(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
N2 Ge1 S1 N1 167.76(11) . . . . ?
Cl1 Ge1 S1 N1 84.17(8) . . . . ?
Se1 Ge1 S1 N1 -94.87(8) . . . . ?
N1 Ge1 S1 N2 -167.76(11) . . . . ?
Cl1 Ge1 S1 N2 -83.59(8) . . . . ?
Se1 Ge1 S1 N2 97.37(8) . . . . ?
N2 Ge1 S1 C5 84.55(11) . . . . ?
N1 Ge1 S1 C5 -83.21(10) . . . . ?
Cl1 Ge1 S1 C5 0.96(8) . . . . ?
Se1 Ge1 S1 C5 -178.08(7) . . . . ?
N4 Ge2 S2 N3 162.05(12) . . . . ?
Cl2 Ge2 S2 N3 78.60(8) . . . . ?
Se2 Ge2 S2 N3 -101.19(8) . . . . ?
N3 Ge2 S2 N4 -162.05(12) . . . . ?
Cl2 Ge2 S2 N4 -83.45(8) . . . . ?
Se2 Ge2 S2 N4 96.76(8) . . . . ?
N3 Ge2 S2 C19 -82.37(11) . . . . ?
N4 Ge2 S2 C19 79.69(11) . . . . ?
Cl2 Ge2 S2 C19 -3.76(8) . . . . ?
Se2 Ge2 S2 C19 176.45(8) . . . . ?
N3 S2 C19 C20 -55.50(19) . . . . ?
N4 S2 C19 C20 37.51(19) . . . . ?
Ge2 S2 C19 C20 -8.7(2) . . . . ?
N3 S2 C19 C24 126.53(15) . . . . ?
N4 S2 C19 C24 -140.45(15) . . . . ?
Ge2 S2 C19 C24 173.32(13) . . . . ?
N3 S2 N4 C25 -160.18(15) . . . . ?
C19 S2 N4 C25 93.22(15) . . . . ?
Ge2 S2 N4 C25 -147.62(18) . . . . ?
N3 S2 N4 Ge2 -12.56(8) . . . . ?
C19 S2 N4 Ge2 -119.16(8) . . . . ?
N3 Ge2 N4 C25 153.61(18) . . . . ?
Cl2 Ge2 N4 C25 -106.14(16) . . . . ?
Se2 Ge2 N4 C25 31.12(19) . . . . ?
S2 Ge2 N4 C25 142.3(2) . . . . ?
N3 Ge2 N4 S2 11.36(7) . . . . ?
Cl2 Ge2 N4 S2 111.60(6) . . . . ?
Se2 Ge2 N4 S2 -111.14(6) . . . . ?
N4 S2 N3 C15 165.29(16) . . . . ?
C19 S2 N3 C15 -89.95(16) . . . . ?
Ge2 S2 N3 C15 152.64(19) . . . . ?
N4 S2 N3 Ge2 12.65(8) . . . . ?
C19 S2 N3 Ge2 117.41(9) . . . . ?
N4 Ge2 N3 C15 -159.72(19) . . . . ?
Cl2 Ge2 N3 C15 96.58(17) . . . . ?
Se2 Ge2 N3 C15 -40.1(2) . . . . ?
S2 Ge2 N3 C15 -148.3(2) . . . . ?
N4 Ge2 N3 S2 -11.38(7) . . . . ?
Cl2 Ge2 N3 S2 -115.07(6) . . . . ?
Se2 Ge2 N3 S2 108.22(6) . . . . ?
N2 S1 N1 C1 151.72(14) . . . . ?
C5 S1 N1 C1 -102.18(14) . . . . ?
Ge1 S1 N1 C1 143.01(16) . . . . ?
N2 S1 N1 Ge1 8.71(8) . . . . ?
C5 S1 N1 Ge1 114.81(8) . . . . ?
N2 Ge1 N1 C1 -144.28(17) . . . . ?
Cl1 Ge1 N1 C1 114.70(15) . . . . ?
Se1 Ge1 N1 C1 -19.43(18) . . . . ?
S1 Ge1 N1 C1 -136.5(2) . . . . ?
N2 Ge1 N1 S1 -7.82(7) . . . . ?
Cl1 Ge1 N1 S1 -108.83(6) . . . . ?
Se1 Ge1 N1 S1 117.04(6) . . . . ?
N1 S1 N2 C11 -151.68(15) . . . . ?
C5 S1 N2 C11 103.04(15) . . . . ?
Ge1 S1 N2 C11 -142.97(17) . . . . ?
N1 S1 N2 Ge1 -8.71(8) . . . . ?
C5 S1 N2 Ge1 -113.98(8) . . . . ?
N1 Ge1 N2 C11 144.35(17) . . . . ?
Cl1 Ge1 N2 C11 -114.14(16) . . . . ?
Se1 Ge1 N2 C11 20.87(19) . . . . ?
S1 Ge1 N2 C11 136.6(2) . . . . ?
N1 Ge1 N2 S1 7.78(7) . . . . ?
Cl1 Ge1 N2 S1 109.30(6) . . . . ?
Se1 Ge1 N2 S1 -115.70(6) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C7 C6 C5 C10 0.3(3) . . . . ?
C7 C6 C5 S1 179.12(16) . . . . ?
N1 S1 C5 C6 -37.11(19) . . . . ?
N2 S1 C5 C6 57.52(19) . . . . ?
Ge1 S1 C5 C6 10.0(2) . . . . ?
N1 S1 C5 C10 141.78(16) . . . . ?
N2 S1 C5 C10 -123.58(16) . . . . ?
Ge1 S1 C5 C10 -171.11(13) . . . . ?
C24 C19 C20 C21 1.0(3) . . . . ?
S2 C19 C20 C21 -176.83(16) . . . . ?
S1 N2 C11 C12 -179.42(14) . . . . ?
Ge1 N2 C11 C12 52.1(2) . . . . ?
S1 N2 C11 C14 -60.3(2) . . . . ?
Ge1 N2 C11 C14 171.22(14) . . . . ?
S1 N2 C11 C13 60.3(2) . . . . ?
Ge1 N2 C11 C13 -68.2(2) . . . . ?
C21 C22 C23 C24 1.2(3) . . . . ?
S2 N4 C25 C26 -168.46(13) . . . . ?
Ge2 N4 C25 C26 56.7(2) . . . . ?
S2 N4 C25 C27 72.23(19) . . . . ?
Ge2 N4 C25 C27 -62.6(2) . . . . ?
S2 N4 C25 C28 -50.0(2) . . . . ?
Ge2 N4 C25 C28 175.18(14) . . . . ?
C22 C23 C24 C19 -1.4(3) . . . . ?
C20 C19 C24 C23 0.3(3) . . . . ?
S2 C19 C24 C23 178.29(16) . . . . ?
C19 C20 C21 C22 -1.3(3) . . . . ?
C23 C22 C21 C20 0.2(3) . . . . ?
S2 N3 C15 C18 -62.4(2) . . . . ?
Ge2 N3 C15 C18 79.3(2) . . . . ?
S2 N3 C15 C16 177.84(14) . . . . ?
Ge2 N3 C15 C16 -40.4(2) . . . . ?
S2 N3 C15 C17 60.5(2) . . . . ?
Ge2 N3 C15 C17 -157.74(15) . . . . ?
S1 N1 C1 C2 175.64(12) . . . . ?
Ge1 N1 C1 C2 -55.8(2) . . . . ?
S1 N1 C1 C3 57.36(19) . . . . ?
Ge1 N1 C1 C3 -174.12(13) . . . . ?
S1 N1 C1 C4 -64.30(19) . . . . ?
Ge1 N1 C1 C4 64.2(2) . . . . ?
C6 C5 C10 C9 -0.3(3) . . . . ?
S1 C5 C10 C9 -179.16(15) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C5 C10 C9 C8 0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_naka183
_database_code_depnum_ccdc_archive 'CCDC 1535392'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C21 H37 Cl2 Ge2 N4 S2 Si3
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H38 Cl2 Ge2 N4 S2 Si3'
_chemical_formula_sum            'C21 H38 Cl2 Ge2 N4 S2 Si3'
_chemical_formula_weight         711.02

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'
Si Si 0.0817 0.0704 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 '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'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   10.372(2)
_cell_length_b                   10.737(2)
_cell_length_c                   16.616(4)
_cell_angle_alpha                106.556(3)
_cell_angle_beta                 97.759(3)
_cell_angle_gamma                108.288(2)
_cell_volume                     1632.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3517
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.26

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.261
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8224
_exptl_absorpt_correction_T_max  0.8953
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7761
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5854
_reflns_number_gt                4470
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0275P)²+0.0012P] 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         5854
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
Ge1 Ge 0.16502(4) 0.40077(4) 0.16454(2) 0.01747(10) Uani 1 1 d . . .
Ge2 Ge 0.01107(4) 0.45913(4) 0.33511(2) 0.02072(11) Uani 1 1 d . . .
S2 S -0.13253(10) 0.22094(9) 0.17166(6) 0.0184(2) Uani 1 1 d . . .
Cl1 Cl 0.14660(10) 0.17663(10) 0.07658(6) 0.0251(2) Uani 1 1 d . . .
S1 S 0.31379(10) 0.44354(9) 0.35584(6) 0.0187(2) Uani 1 1 d . . .
Si2 Si 0.31459(12) 0.71328(11) 0.44981(7) 0.0233(2) Uani 1 1 d . . .
Cl2 Cl 0.01282(11) 0.64467(9) 0.28575(6) 0.0303(2) Uani 1 1 d . . .
Si3 Si -0.25863(12) -0.08295(10) 0.15018(7) 0.0231(2) Uani 1 1 d . . .
Si1 Si 0.48711(12) 0.43606(11) 0.23238(7) 0.0262(3) Uani 1 1 d . . .
N4 N -0.1273(4) 0.0645(3) 0.1457(2) 0.0215(7) Uani 1 1 d . . .
H29 H -0.071(4) 0.057(4) 0.120(2) 0.018(11) Uiso 1 1 d . . .
C18 C -0.2024(4) 0.1365(4) -0.0083(2) 0.0245(9) Uani 1 1 d . . .
H28 H -0.2132 0.0451 -0.0088 0.029 Uiso 1 1 calc R . .
C5 C 0.2018(4) 0.1548(4) 0.2979(2) 0.0232(9) Uani 1 1 d . . .
H10 H 0.2334 0.1572 0.2471 0.028 Uiso 1 1 calc R . .
C4 C 0.2131(4) 0.2773(4) 0.3604(2) 0.0198(8) Uani 1 1 d . . .
C14 C -0.1529(4) 0.3797(4) 0.0706(2) 0.0232(9) Uani 1 1 d . . .
H24 H -0.1293 0.4540 0.1242 0.028 Uiso 1 1 calc R . .
C15 C -0.1765(4) 0.4023(4) -0.0071(2) 0.0261(9) Uani 1 1 d . . .
H25 H -0.1696 0.4927 -0.0069 0.031 Uiso 1 1 calc R . .
C13 C -0.1645(4) 0.2453(4) 0.0689(2) 0.0187(8) Uani 1 1 d . . .
C9 C 0.1679(4) 0.2749(4) 0.4353(2) 0.0239(9) Uani 1 1 d . . .
H14 H 0.1753 0.3591 0.4779 0.029 Uiso 1 1 calc R . .
C21 C -0.1816(4) -0.2200(4) 0.1348(3) 0.0302(10) Uani 1 1 d . . .
H36 H -0.1264 -0.2147 0.0916 0.045 Uiso 1 1 calc R . .
H37 H -0.2569 -0.3124 0.1148 0.045 Uiso 1 1 calc R . .
H38 H -0.1208 -0.2052 0.1900 0.045 Uiso 1 1 calc R . .
C6 C 0.1438(4) 0.0284(4) 0.3102(3) 0.0271(9) Uani 1 1 d . . .
H11 H 0.1340 -0.0564 0.2671 0.033 Uiso 1 1 calc R . .
C8 C 0.1116(4) 0.1470(4) 0.4465(3) 0.0329(10) Uani 1 1 d . . .
H13 H 0.0807 0.1437 0.4974 0.039 Uiso 1 1 calc R . .
C16 C -0.2100(4) 0.2944(4) -0.0847(2) 0.0268(9) Uani 1 1 d . . .
H26 H -0.2229 0.3116 -0.1376 0.032 Uiso 1 1 calc R . .
C17 C -0.2250(4) 0.1611(4) -0.0857(2) 0.0282(9) Uani 1 1 d . . .
H27 H -0.2506 0.0865 -0.1394 0.034 Uiso 1 1 calc R . .
C7 C 0.1005(4) 0.0254(4) 0.3844(3) 0.0324(10) Uani 1 1 d . . .
H12 H 0.0626 -0.0614 0.3929 0.039 Uiso 1 1 calc R . .
C19 C -0.2960(5) -0.0307(5) 0.2581(3) 0.0459(12) Uani 1 1 d . . .
H30 H -0.2121 -0.0072 0.3032 0.069 Uiso 1 1 calc R . .
H31 H -0.3729 -0.1084 0.2619 0.069 Uiso 1 1 calc R . .
H32 H -0.3228 0.0509 0.2664 0.069 Uiso 1 1 calc R . .
C20 C -0.4178(4) -0.1362(4) 0.0641(3) 0.0374(11) Uani 1 1 d . . .
H33 H -0.4502 -0.0581 0.0712 0.056 Uiso 1 1 calc R . .
H34 H -0.4913 -0.2164 0.0679 0.056 Uiso 1 1 calc R . .
H35 H -0.3964 -0.1622 0.0074 0.056 Uiso 1 1 calc R . .
N3 N 0.0193(3) 0.3376(3) 0.22462(17) 0.0158(6) Uani 1 1 d . . .
N2 N 0.2182(3) 0.5361(3) 0.38210(18) 0.0182(7) Uani 1 1 d . . .
N1 N 0.3226(3) 0.4180(3) 0.25668(17) 0.0186(7) Uani 1 1 d . . .
C10 C 0.3836(4) 0.8216(4) 0.3847(3) 0.0320(10) Uani 1 1 d . . .
H15 H 0.4455 0.7852 0.3538 0.048 Uiso 1 1 calc R . .
H16 H 0.4365 0.9186 0.4231 0.048 Uiso 1 1 calc R . .
H17 H 0.3054 0.8184 0.3428 0.048 Uiso 1 1 calc R . .
C12 C 0.4631(5) 0.7205(4) 0.5297(3) 0.0393(11) Uani 1 1 d . . .
H21 H 0.4281 0.6534 0.5586 0.059 Uiso 1 1 calc R . .
H22 H 0.5074 0.8151 0.5730 0.059 Uiso 1 1 calc R . .
H23 H 0.5319 0.6969 0.4998 0.059 Uiso 1 1 calc R . .
C11 C 0.1936(5) 0.7734(4) 0.5083(2) 0.0361(11) Uani 1 1 d . . .
H18 H 0.1107 0.7618 0.4664 0.054 Uiso 1 1 calc R . .
H19 H 0.2410 0.8724 0.5445 0.054 Uiso 1 1 calc R . .
H20 H 0.1648 0.7180 0.5450 0.054 Uiso 1 1 calc R . .
C2 C 0.4842(4) 0.4824(4) 0.1324(3) 0.0360(10) Uani 1 1 d . . .
H4 H 0.4052 0.4105 0.0857 0.054 Uiso 1 1 calc R . .
H5 H 0.5720 0.4880 0.1152 0.054 Uiso 1 1 calc R . .
H6 H 0.4739 0.5731 0.1438 0.054 Uiso 1 1 calc R . .
C1 C 0.5152(5) 0.2677(5) 0.2127(3) 0.0371(11) Uani 1 1 d . . .
H1 H 0.5115 0.2410 0.2643 0.056 Uiso 1 1 calc R . .
H2 H 0.6070 0.2790 0.2002 0.056 Uiso 1 1 calc R . .
H3 H 0.4417 0.1945 0.1632 0.056 Uiso 1 1 calc R . .
C3 C 0.6300(4) 0.5753(5) 0.3234(3) 0.0423(12) Uani 1 1 d . . .
H7 H 0.6180 0.6649 0.3322 0.063 Uiso 1 1 calc R . .
H8 H 0.7205 0.5824 0.3099 0.063 Uiso 1 1 calc R . .
H9 H 0.6268 0.5524 0.3763 0.063 Uiso 1 1 calc R . .


_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
Ge1 N3 1.973(3) . ?
Ge1 N1 2.006(3) . ?
Ge1 Cl1 2.3655(10) . ?
Ge2 N3 1.957(3) . ?
Ge2 N2 1.993(3) . ?
Ge2 Cl2 2.3568(10) . ?
S2 N3 1.607(3) . ?
S2 N4 1.632(3) . ?
S2 C13 1.803(4) . ?
S1 N1 1.612(3) . ?
S1 N2 1.628(3) . ?
S1 C4 1.792(4) . ?
Si2 N2 1.779(3) . ?
Si2 C11 1.849(4) . ?
Si2 C10 1.855(4) . ?
Si2 C12 1.859(4) . ?
Si3 N4 1.763(3) . ?
Si3 C20 1.845(4) . ?
Si3 C19 1.852(4) . ?
Si3 C21 1.857(4) . ?
Si1 N1 1.770(3) . ?
Si1 C3 1.853(4) . ?
Si1 C2 1.864(4) . ?
Si1 C1 1.865(4) . ?
C18 C13 1.373(5) . ?
C18 C17 1.389(5) . ?
C5 C4 1.383(5) . ?
C5 C6 1.386(5) . ?
C4 C9 1.391(5) . ?
C14 C15 1.384(5) . ?
C14 C13 1.402(5) . ?
C15 C16 1.378(5) . ?
C9 C8 1.391(5) . ?
C6 C7 1.375(5) . ?
C8 C7 1.374(5) . ?
C16 C17 1.386(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
N3 Ge1 N1 94.29(11) . . ?
N3 Ge1 Cl1 97.25(8) . . ?
N1 Ge1 Cl1 93.14(8) . . ?
N3 Ge2 N2 93.30(12) . . ?
N3 Ge2 Cl2 94.83(8) . . ?
N2 Ge2 Cl2 93.86(8) . . ?
N3 S2 N4 110.74(16) . . ?
N3 S2 C13 105.00(15) . . ?
N4 S2 C13 103.57(17) . . ?
N1 S1 N2 110.57(15) . . ?
N1 S1 C4 106.79(16) . . ?
N2 S1 C4 103.18(16) . . ?
N2 Si2 C11 106.59(18) . . ?
N2 Si2 C10 110.76(16) . . ?
C11 Si2 C10 112.02(18) . . ?
N2 Si2 C12 109.06(16) . . ?
C11 Si2 C12 108.97(19) . . ?
C10 Si2 C12 109.4(2) . . ?
N4 Si3 C20 109.80(17) . . ?
N4 Si3 C19 106.96(19) . . ?
C20 Si3 C19 110.2(2) . . ?
N4 Si3 C21 105.07(17) . . ?
C20 Si3 C21 111.88(18) . . ?
C19 Si3 C21 112.7(2) . . ?
N1 Si1 C3 110.27(17) . . ?
N1 Si1 C2 107.31(17) . . ?
C3 Si1 C2 110.3(2) . . ?
N1 Si1 C1 110.00(17) . . ?
C3 Si1 C1 109.2(2) . . ?
C2 Si1 C1 109.69(19) . . ?
S2 N4 Si3 124.3(2) . . ?
C13 C18 C17 119.5(3) . . ?
C4 C5 C6 119.3(3) . . ?
C5 C4 C9 120.8(3) . . ?
C5 C4 S1 120.3(3) . . ?
C9 C4 S1 118.0(3) . . ?
C15 C14 C13 118.8(3) . . ?
C16 C15 C14 120.4(3) . . ?
C18 C13 C14 120.9(3) . . ?
C18 C13 S2 121.8(3) . . ?
C14 C13 S2 117.2(3) . . ?
C8 C9 C4 118.8(3) . . ?
C7 C6 C5 120.2(4) . . ?
C7 C8 C9 120.4(4) . . ?
C15 C16 C17 120.3(4) . . ?
C16 C17 C18 120.0(4) . . ?
C8 C7 C6 120.4(4) . . ?
S2 N3 Ge2 111.28(15) . . ?
S2 N3 Ge1 121.17(15) . . ?
Ge2 N3 Ge1 122.03(14) . . ?
S1 N2 Si2 114.64(17) . . ?
S1 N2 Ge2 122.14(16) . . ?
Si2 N2 Ge2 123.10(15) . . ?
S1 N1 Si1 118.33(17) . . ?
S1 N1 Ge1 122.50(16) . . ?
Si1 N1 Ge1 118.25(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
N3 S2 N4 Si3 139.4(2) . . . . ?
C13 S2 N4 Si3 -108.5(2) . . . . ?
C20 Si3 N4 S2 70.3(3) . . . . ?
C19 Si3 N4 S2 -49.3(3) . . . . ?
C21 Si3 N4 S2 -169.2(2) . . . . ?
C6 C5 C4 C9 0.4(5) . . . . ?
C6 C5 C4 S1 169.3(3) . . . . ?
N1 S1 C4 C5 22.6(3) . . . . ?
N2 S1 C4 C5 139.2(3) . . . . ?
N1 S1 C4 C9 -168.2(3) . . . . ?
N2 S1 C4 C9 -51.6(3) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
C17 C18 C13 C14 2.2(6) . . . . ?
C17 C18 C13 S2 -179.6(3) . . . . ?
C15 C14 C13 C18 -1.8(6) . . . . ?
C15 C14 C13 S2 179.9(3) . . . . ?
N3 S2 C13 C18 127.7(3) . . . . ?
N4 S2 C13 C18 11.5(4) . . . . ?
N3 S2 C13 C14 -54.1(3) . . . . ?
N4 S2 C13 C14 -170.3(3) . . . . ?
C5 C4 C9 C8 0.4(5) . . . . ?
S1 C4 C9 C8 -168.8(3) . . . . ?
C4 C5 C6 C7 -1.2(6) . . . . ?
C4 C9 C8 C7 -0.3(6) . . . . ?
C14 C15 C16 C17 2.1(6) . . . . ?
C15 C16 C17 C18 -1.8(6) . . . . ?
C13 C18 C17 C16 -0.4(6) . . . . ?
C9 C8 C7 C6 -0.5(6) . . . . ?
C5 C6 C7 C8 1.3(6) . . . . ?
N4 S2 N3 Ge2 -125.78(17) . . . . ?
C13 S2 N3 Ge2 123.05(16) . . . . ?
N4 S2 N3 Ge1 80.0(2) . . . . ?
C13 S2 N3 Ge1 -31.2(2) . . . . ?
N2 Ge2 N3 S2 165.04(15) . . . . ?
Cl2 Ge2 N3 S2 -100.81(13) . . . . ?
N2 Ge2 N3 Ge1 -40.95(16) . . . . ?
Cl2 Ge2 N3 Ge1 53.20(15) . . . . ?
N1 Ge1 N3 S2 -142.51(17) . . . . ?
Cl1 Ge1 N3 S2 -48.78(17) . . . . ?
N1 Ge1 N3 Ge2 66.00(16) . . . . ?
Cl1 Ge1 N3 Ge2 159.72(13) . . . . ?
N1 S1 N2 Si2 -105.28(19) . . . . ?
C4 S1 N2 Si2 140.84(18) . . . . ?
N1 S1 N2 Ge2 70.8(2) . . . . ?
C4 S1 N2 Ge2 -43.1(2) . . . . ?
C11 Si2 N2 S1 -155.92(18) . . . . ?
C10 Si2 N2 S1 82.0(2) . . . . ?
C12 Si2 N2 S1 -38.4(2) . . . . ?
C11 Si2 N2 Ge2 28.0(2) . . . . ?
C10 Si2 N2 Ge2 -94.0(2) . . . . ?
C12 Si2 N2 Ge2 145.6(2) . . . . ?
N3 Ge2 N2 S1 -32.04(19) . . . . ?
Cl2 Ge2 N2 S1 -127.11(17) . . . . ?
N3 Ge2 N2 Si2 143.70(18) . . . . ?
Cl2 Ge2 N2 Si2 48.63(17) . . . . ?
N2 S1 N1 Si1 136.76(18) . . . . ?
C4 S1 N1 Si1 -111.68(19) . . . . ?
N2 S1 N1 Ge1 -32.0(2) . . . . ?
C4 S1 N1 Ge1 79.5(2) . . . . ?
C3 Si1 N1 S1 -34.1(2) . . . . ?
C2 Si1 N1 S1 -154.3(2) . . . . ?
C1 Si1 N1 S1 86.5(2) . . . . ?
C3 Si1 N1 Ge1 135.2(2) . . . . ?
C2 Si1 N1 Ge1 15.0(2) . . . . ?
C1 Si1 N1 Ge1 -104.3(2) . . . . ?
N3 Ge1 N1 S1 -24.93(19) . . . . ?
Cl1 Ge1 N1 S1 -122.45(17) . . . . ?
N3 Ge1 N1 Si1 166.26(16) . . . . ?
Cl1 Ge1 N1 Si1 68.74(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.580
_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_naka291
_database_code_depnum_ccdc_archive 'CCDC 1535391'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'C28 H46 Cl2 N4 S2 Se2 Sn2, C6 H6' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H46 Cl2 N4 S2 Se2 Sn2, C6 H6'
_chemical_formula_sum            'C34 H52 Cl2 N4 S2 Se2 Sn2'
_chemical_formula_weight         1047.12

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'
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 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   13.0087(12)
_cell_length_b                   11.6396(10)
_cell_length_c                   14.1127(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.0450(10)
_cell_angle_gamma                90.00
_cell_volume                     2125.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7713
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.53

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036
_exptl_absorpt_coefficient_mu    3.140
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7653
_exptl_absorpt_correction_T_max  0.8101
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11041
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4386
_reflns_number_gt                3994
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX-II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_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)+(0.0316P)²+0.0019P] 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         4386
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.136524(12) 0.474933(15) 0.011095(11) 0.01417(7) Uani 1 1 d . . .
Se1 Se 0.001063(19) 0.50335(3) 0.129961(18) 0.02116(9) Uani 1 1 d . . .
S1 S 0.27796(4) 0.28203(5) 0.00071(4) 0.01354(13) Uani 1 1 d . . .
Cl1 Cl 0.23803(5) 0.64431(6) 0.03631(4) 0.02633(15) Uani 1 1 d . . .
N2 N 0.22363(14) 0.34379(19) 0.08773(13) 0.0157(4) Uani 1 1 d . . .
C8 C 0.0829(2) -0.0349(3) -0.08340(19) 0.0233(6) Uani 1 1 d . . .
H12 H 0.0423 -0.1014 -0.0988 0.028 Uiso 1 1 calc R . .
N1 N 0.23929(14) 0.38312(19) -0.07493(13) 0.0156(4) Uani 1 1 d . . .
C9 C 0.1818(2) -0.0462(2) -0.03608(18) 0.0220(5) Uani 1 1 d . . .
H13 H 0.2093 -0.1202 -0.0202 0.026 Uiso 1 1 calc R . .
C5 C 0.19956(17) 0.1590(2) -0.03567(15) 0.0143(5) Uani 1 1 d . . .
C10 C 0.24030(18) 0.0520(2) -0.01217(17) 0.0184(5) Uani 1 1 d . . .
H14 H 0.3079 0.0453 0.0201 0.022 Uiso 1 1 calc R . .
C7 C 0.04343(18) 0.0729(3) -0.10811(18) 0.0228(6) Uani 1 1 d . . .
H11 H -0.0237 0.0796 -0.1413 0.027 Uiso 1 1 calc R . .
C6 C 0.10116(16) 0.1710(2) -0.08474(16) 0.0188(5) Uani 1 1 d . . .
H10 H 0.0743 0.2449 -0.1018 0.023 Uiso 1 1 calc R . .
C11 C 0.23537(16) 0.2967(2) 0.18710(15) 0.0152(5) Uani 1 1 d . . .
C12 C 0.14505(18) 0.2182(2) 0.20330(17) 0.0224(5) Uani 1 1 d . . .
H15 H 0.0801 0.2608 0.1907 0.034 Uiso 1 1 calc R . .
H16 H 0.1526 0.1912 0.2694 0.034 Uiso 1 1 calc R . .
H17 H 0.1444 0.1522 0.1602 0.034 Uiso 1 1 calc R . .
C13 C 0.23978(19) 0.3999(2) 0.25453(16) 0.0201(5) Uani 1 1 d . . .
H18 H 0.2960 0.4511 0.2406 0.030 Uiso 1 1 calc R . .
H19 H 0.2521 0.3730 0.3206 0.030 Uiso 1 1 calc R . .
H20 H 0.1740 0.4415 0.2456 0.030 Uiso 1 1 calc R . .
C14 C 0.33768(17) 0.2303(2) 0.20572(17) 0.0211(6) Uani 1 1 d . . .
H21 H 0.3347 0.1611 0.1659 0.032 Uiso 1 1 calc R . .
H22 H 0.3487 0.2081 0.2730 0.032 Uiso 1 1 calc R . .
H23 H 0.3949 0.2792 0.1901 0.032 Uiso 1 1 calc R . .
C4 C 0.2530(2) 0.5087(2) -0.20929(19) 0.0234(6) Uani 1 1 d . . .
H7 H 0.1865 0.4822 -0.2408 0.035 Uiso 1 1 calc R . .
H8 H 0.2970 0.5345 -0.2575 0.035 Uiso 1 1 calc R . .
H9 H 0.2415 0.5727 -0.1665 0.035 Uiso 1 1 calc R . .
C1 C 0.30600(17) 0.4106(2) -0.15209(16) 0.0177(5) Uani 1 1 d . . .
C3 C 0.3131(2) 0.3048(3) -0.21539(19) 0.0316(7) Uani 1 1 d . . .
H4 H 0.3446 0.2412 -0.1771 0.047 Uiso 1 1 calc R . .
H5 H 0.3557 0.3228 -0.2668 0.047 Uiso 1 1 calc R . .
H6 H 0.2436 0.2826 -0.2428 0.047 Uiso 1 1 calc R . .
C2 C 0.4140(2) 0.4490(3) -0.1096(2) 0.0348(7) Uani 1 1 d . . .
H1 H 0.4079 0.5168 -0.0694 0.052 Uiso 1 1 calc R . .
H2 H 0.4559 0.4680 -0.1612 0.052 Uiso 1 1 calc R . .
H3 H 0.4472 0.3866 -0.0710 0.052 Uiso 1 1 calc R . .
C16 C 0.4990(2) 0.9511(4) 0.0879(2) 0.0420(9) Uani 1 1 d . . .
H25 H 0.4980 0.9171 0.1489 0.050 Uiso 1 1 calc R . .
C17 C 0.5280(2) 1.0633(4) 0.0812(2) 0.0408(9) Uani 1 1 d . . .
H26 H 0.5476 1.1067 0.1372 0.049 Uiso 1 1 calc R . .
C15 C 0.4712(2) 0.8867(3) 0.0077(3) 0.0449(9) Uani 1 1 d . . .
H24 H 0.4516 0.8086 0.0132 0.054 Uiso 1 1 calc R . .


_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 N2 2.127(2) . ?
Sn1 N1 2.1783(19) . ?
Sn1 Cl1 2.3787(7) . ?
Sn1 Se1 2.5456(3) 3_565 ?
Sn1 Se1 2.5790(3) . ?
Sn1 S1 2.9163(6) . ?
Se1 Sn1 2.5455(3) 3_565 ?
S1 N1 1.632(2) . ?
S1 N2 1.645(2) . ?
S1 C5 1.802(3) . ?
N2 C11 1.498(3) . ?
C8 C7 1.386(4) . ?
C8 C9 1.392(4) . ?
N1 C1 1.497(3) . ?
C9 C10 1.395(4) . ?
C5 C10 1.379(4) . ?
C5 C6 1.397(3) . ?
C7 C6 1.387(4) . ?
C11 C12 1.525(3) . ?
C11 C13 1.529(3) . ?
C11 C14 1.538(3) . ?
C4 C1 1.521(3) . ?
C1 C3 1.530(4) . ?
C1 C2 1.535(4) . ?
C16 C17 1.365(6) . ?
C16 C15 1.374(5) . ?
C17 C15 1.384(5) 3_675 ?
C15 C17 1.384(5) 3_675 ?

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
N2 Sn1 N1 66.80(7) . . ?
N2 Sn1 Cl1 105.14(6) . . ?
N1 Sn1 Cl1 97.26(6) . . ?
N2 Sn1 Se1 139.62(6) . 3_565 ?
N1 Sn1 Se1 92.01(5) . 3_565 ?
Cl1 Sn1 Se1 111.606(19) . 3_565 ?
N2 Sn1 Se1 97.19(5) . . ?
N1 Sn1 Se1 157.96(6) . . ?
Cl1 Sn1 Se1 101.710(19) . . ?
Se1 Sn1 Se1 91.352(11) 3_565 . ?
N2 Sn1 S1 33.70(5) . . ?
N1 Sn1 S1 33.57(5) . . ?
Cl1 Sn1 S1 107.60(2) . . ?
Se1 Sn1 S1 115.628(14) 3_565 . ?
Se1 Sn1 S1 127.543(15) . . ?
Sn1 Se1 Sn1 88.647(11) 3_565 . ?
N1 S1 N2 92.65(10) . . ?
N1 S1 C5 105.10(10) . . ?
N2 S1 C5 106.57(10) . . ?
N1 S1 Sn1 47.56(7) . . ?
N2 S1 Sn1 45.84(7) . . ?
C5 S1 Sn1 106.57(8) . . ?
C11 N2 S1 121.96(16) . . ?
C11 N2 Sn1 137.27(15) . . ?
S1 N2 Sn1 100.47(9) . . ?
C7 C8 C9 120.4(3) . . ?
C1 N1 S1 117.88(15) . . ?
C1 N1 Sn1 137.51(16) . . ?
S1 N1 Sn1 98.87(9) . . ?
C8 C9 C10 119.4(3) . . ?
C10 C5 C6 121.2(2) . . ?
C10 C5 S1 117.21(17) . . ?
C6 C5 S1 121.6(2) . . ?
C5 C10 C9 119.7(2) . . ?
C8 C7 C6 120.5(2) . . ?
C7 C6 C5 118.7(2) . . ?
N2 C11 C12 110.81(17) . . ?
N2 C11 C13 106.8(2) . . ?
C12 C11 C13 110.9(2) . . ?
N2 C11 C14 110.18(18) . . ?
C12 C11 C14 109.9(2) . . ?
C13 C11 C14 108.27(18) . . ?
N1 C1 C4 106.36(19) . . ?
N1 C1 C3 109.1(2) . . ?
C4 C1 C3 110.3(2) . . ?
N1 C1 C2 110.78(19) . . ?
C4 C1 C2 109.5(2) . . ?
C3 C1 C2 110.7(2) . . ?
C17 C16 C15 121.1(3) . . ?
C16 C17 C15 119.5(3) . 3_675 ?
C16 C15 C17 119.4(4) . 3_675 ?

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
N2 Sn1 Se1 Sn1 -140.45(6) . . . 3_565 ?
N1 Sn1 Se1 Sn1 -98.74(13) . . . 3_565 ?
Cl1 Sn1 Se1 Sn1 112.399(19) . . . 3_565 ?
Se1 Sn1 Se1 Sn1 0.0 3_565 . . 3_565 ?
S1 Sn1 Se1 Sn1 -124.318(17) . . . 3_565 ?
N2 Sn1 S1 N1 -167.25(14) . . . . ?
Cl1 Sn1 S1 N1 -76.22(10) . . . . ?
Se1 Sn1 S1 N1 49.28(10) 3_565 . . . ?
Se1 Sn1 S1 N1 162.96(9) . . . . ?
N1 Sn1 S1 N2 167.25(14) . . . . ?
Cl1 Sn1 S1 N2 91.03(10) . . . . ?
Se1 Sn1 S1 N2 -143.47(10) 3_565 . . . ?
Se1 Sn1 S1 N2 -29.79(10) . . . . ?
N2 Sn1 S1 C5 97.23(12) . . . . ?
N1 Sn1 S1 C5 -95.52(12) . . . . ?
Cl1 Sn1 S1 C5 -171.74(8) . . . . ?
Se1 Sn1 S1 C5 -46.24(8) 3_565 . . . ?
Se1 Sn1 S1 C5 67.44(8) . . . . ?
N1 S1 N2 C11 -175.90(18) . . . . ?
C5 S1 N2 C11 77.48(19) . . . . ?
Sn1 S1 N2 C11 174.7(2) . . . . ?
N1 S1 N2 Sn1 9.39(10) . . . . ?
C5 S1 N2 Sn1 -97.23(11) . . . . ?
N1 Sn1 N2 C11 179.0(2) . . . . ?
Cl1 Sn1 N2 C11 87.5(2) . . . . ?
Se1 Sn1 N2 C11 -117.4(2) 3_565 . . . ?
Se1 Sn1 N2 C11 -16.8(2) . . . . ?
S1 Sn1 N2 C11 -173.4(3) . . . . ?
N1 Sn1 N2 S1 -7.63(8) . . . . ?
Cl1 Sn1 N2 S1 -99.15(8) . . . . ?
Se1 Sn1 N2 S1 55.94(13) 3_565 . . . ?
Se1 Sn1 N2 S1 156.60(8) . . . . ?
N2 S1 N1 C1 148.83(18) . . . . ?
C5 S1 N1 C1 -103.22(18) . . . . ?
Sn1 S1 N1 C1 158.0(2) . . . . ?
N2 S1 N1 Sn1 -9.12(10) . . . . ?
C5 S1 N1 Sn1 98.83(10) . . . . ?
N2 Sn1 N1 C1 -142.9(2) . . . . ?
Cl1 Sn1 N1 C1 -39.5(2) . . . . ?
Se1 Sn1 N1 C1 72.6(2) 3_565 . . . ?
Se1 Sn1 N1 C1 171.17(14) . . . . ?
S1 Sn1 N1 C1 -150.6(3) . . . . ?
N2 Sn1 N1 S1 7.66(8) . . . . ?
Cl1 Sn1 N1 S1 111.06(8) . . . . ?
Se1 Sn1 N1 S1 -136.86(8) 3_565 . . . ?
Se1 Sn1 N1 S1 -38.25(18) . . . . ?
C7 C8 C9 C10 1.1(4) . . . . ?
N1 S1 C5 C10 154.14(18) . . . . ?
N2 S1 C5 C10 -108.38(19) . . . . ?
Sn1 S1 C5 C10 -156.32(17) . . . . ?
N1 S1 C5 C6 -26.5(2) . . . . ?
N2 S1 C5 C6 71.0(2) . . . . ?
Sn1 S1 C5 C6 23.0(2) . . . . ?
C6 C5 C10 C9 -1.2(4) . . . . ?
S1 C5 C10 C9 178.14(18) . . . . ?
C8 C9 C10 C5 0.0(4) . . . . ?
C9 C8 C7 C6 -1.0(4) . . . . ?
C8 C7 C6 C5 -0.2(4) . . . . ?
C10 C5 C6 C7 1.3(3) . . . . ?
S1 C5 C6 C7 -178.02(18) . . . . ?
S1 N2 C11 C12 -94.4(2) . . . . ?
Sn1 N2 C11 C12 78.0(3) . . . . ?
S1 N2 C11 C13 144.79(17) . . . . ?
Sn1 N2 C11 C13 -42.9(3) . . . . ?
S1 N2 C11 C14 27.4(3) . . . . ?
Sn1 N2 C11 C14 -160.25(19) . . . . ?
S1 N1 C1 C4 -178.52(17) . . . . ?
Sn1 N1 C1 C4 -31.8(3) . . . . ?
S1 N1 C1 C3 62.5(2) . . . . ?
Sn1 N1 C1 C3 -150.78(19) . . . . ?
S1 N1 C1 C2 -59.6(3) . . . . ?
Sn1 N1 C1 C2 87.1(3) . . . . ?
C15 C16 C17 C15 0.5(5) . . . 3_675 ?
C17 C16 C15 C17 -0.5(5) . . . 3_675 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.937
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.118
