# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_compound3__bau14c_multiscan
_database_code_depnum_ccdc_archive 'CCDC 1499674'
_audit_update_record             
;
2016-08-18 deposited with the CCDC.
2016-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 Cl2 N2 S4 Si, C2 H3 N'
_chemical_formula_sum            'C28 H23 Cl2 N3 S4 Si'
_chemical_formula_weight         628.72

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.1870(19)
_cell_length_b                   11.779(2)
_cell_length_c                   12.474(2)
_cell_angle_alpha                82.74(2)
_cell_angle_beta                 80.73(2)
_cell_angle_gamma                83.53(2)
_cell_volume                     1458.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      29.15

_exptl_crystal_description       block
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          .65
_exptl_crystal_size_mid          .5
_exptl_crystal_size_min          .35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.7153
_exptl_absorpt_correction_T_max  0.8520

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Stoe-IPDS
_diffrn_measurement_method       Stoe-IPDS
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16507
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5564
_reflns_number_gt                4954
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Stoe-IPDS
_computing_cell_refinement       Stoe-IPDS
_computing_data_reduction        Stoe-IPDS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP/POV-Ray
_computing_publication_material  Bruker-SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0434P)²+0.3251P] 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         5564
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Cl1 Cl -0.08699(4) 0.31305(3) 0.16041(3) 0.03388(10) Uani 1 1 d . . .
Cl2 Cl -0.14753(3) 0.26842(3) 0.41386(3) 0.03247(10) Uani 1 1 d . . .
S1 S 0.14718(3) 0.35473(3) 0.28993(3) 0.02430(9) Uani 1 1 d . . .
S2 S 0.14528(3) 0.13638(3) 0.41965(3) 0.02411(9) Uani 1 1 d . . .
S3 S -0.06681(3) 0.04067(3) 0.29280(3) 0.02456(9) Uani 1 1 d . . .
S4 S 0.16625(3) 0.12457(3) 0.15746(3) 0.02675(9) Uani 1 1 d . . .
Si Si 0.01160(3) 0.21574(3) 0.28793(3) 0.02096(9) Uani 1 1 d . . .
N1 N 0.33027(11) 0.28328(10) 0.42099(10) 0.0236(2) Uani 1 1 d . . .
N2 N 0.10455(12) -0.09088(10) 0.16205(10) 0.0252(3) Uani 1 1 d . . .
N3 N 0.3177(2) 0.38297(17) 0.00518(17) 0.0695(6) Uani 1 1 d . . .
C1 C 0.22172(13) 0.26002(11) 0.38359(12) 0.0221(3) Uani 1 1 d . . .
C2 C 0.38920(13) 0.39017(12) 0.38085(12) 0.0240(3) Uani 1 1 d . . .
C3 C 0.34410(15) 0.48643(13) 0.43296(14) 0.0316(3) Uani 1 1 d . . .
H3 H 0.2747 0.4833 0.4937 0.038 Uiso 1 1 calc R . .
C4 C 0.40156(18) 0.58833(14) 0.39541(16) 0.0402(4) Uani 1 1 d . . .
H4 H 0.3697 0.6559 0.4295 0.048 Uiso 1 1 calc R . .
C5 C 0.50444(18) 0.59200(15) 0.30905(16) 0.0422(4) Uani 1 1 d . . .
H5 H 0.5440 0.6617 0.2845 0.051 Uiso 1 1 calc R . .
C6 C 0.54996(19) 0.49506(17) 0.25838(17) 0.0476(5) Uani 1 1 d . . .
H6 H 0.6219 0.4977 0.1996 0.057 Uiso 1 1 calc R . .
C7 C 0.49117(17) 0.39316(15) 0.29282(15) 0.0383(4) Uani 1 1 d . . .
H7 H 0.5205 0.3266 0.2565 0.046 Uiso 1 1 calc R . .
C8 C 0.39282(13) 0.20565(11) 0.50205(13) 0.0248(3) Uani 1 1 d . . .
C9 C 0.31940(15) 0.17265(13) 0.60221(13) 0.0299(3) Uani 1 1 d . . .
H9 H 0.2277 0.1996 0.6181 0.036 Uiso 1 1 calc R . .
C10 C 0.38173(17) 0.09929(14) 0.67955(15) 0.0370(4) Uani 1 1 d . . .
H10 H 0.3325 0.0762 0.7487 0.044 Uiso 1 1 calc R . .
C11 C 0.51534(17) 0.06004(13) 0.65563(16) 0.0402(4) Uani 1 1 d . . .
H11 H 0.5571 0.0086 0.7078 0.048 Uiso 1 1 calc R . .
C12 C 0.58798(16) 0.09547(13) 0.55611(17) 0.0391(4) Uani 1 1 d . . .
H12 H 0.6802 0.0697 0.5408 0.047 Uiso 1 1 calc R . .
C13 C 0.52735(14) 0.16837(13) 0.47826(15) 0.0318(3) Uani 1 1 d . . .
H13 H 0.5772 0.1924 0.4096 0.038 Uiso 1 1 calc R . .
C14 C 0.07281(13) 0.01113(12) 0.19921(12) 0.0237(3) Uani 1 1 d . . .
C15 C 0.03262(14) -0.19038(12) 0.20572(13) 0.0267(3) Uani 1 1 d . . .
C16 C -0.05007(16) -0.22995(15) 0.14368(15) 0.0362(4) Uani 1 1 d . . .
H16 H -0.0671 -0.1885 0.0761 0.043 Uiso 1 1 calc R . .
C17 C -0.10784(18) -0.33196(16) 0.18240(17) 0.0448(4) Uani 1 1 d . . .
H17 H -0.1648 -0.3604 0.1409 0.054 Uiso 1 1 calc R . .
C18 C -0.08286(18) -0.39185(14) 0.28059(17) 0.0428(4) Uani 1 1 d . . .
H18 H -0.1215 -0.4619 0.3056 0.051 Uiso 1 1 calc R . .
C19 C -0.00198(17) -0.35048(14) 0.34269(16) 0.0392(4) Uani 1 1 d . . .
H19 H 0.0136 -0.3914 0.4108 0.047 Uiso 1 1 calc R . .
C20 C 0.05653(15) -0.24912(13) 0.30564(14) 0.0327(3) Uani 1 1 d . . .
H20 H 0.1122 -0.2202 0.3480 0.039 Uiso 1 1 calc R . .
C21 C 0.22513(14) -0.11080(12) 0.08440(13) 0.0265(3) Uani 1 1 d . . .
C22 C 0.21661(15) -0.10562(13) -0.02499(13) 0.0312(3) Uani 1 1 d . . .
H22 H 0.1331 -0.0861 -0.0504 0.037 Uiso 1 1 calc R . .
C23 C 0.33248(16) -0.12941(14) -0.09807(14) 0.0360(4) Uani 1 1 d . . .
H23 H 0.3280 -0.1275 -0.1738 0.043 Uiso 1 1 calc R . .
C24 C 0.45376(16) -0.15570(15) -0.06042(16) 0.0404(4) Uani 1 1 d . . .
H24 H 0.5327 -0.1707 -0.1105 0.048 Uiso 1 1 calc R . .
C25 C 0.46080(16) -0.16023(16) 0.04969(17) 0.0436(4) Uani 1 1 d . . .
H25 H 0.5447 -0.1778 0.0750 0.052 Uiso 1 1 calc R . .
C26 C 0.34586(16) -0.13924(15) 0.12350(15) 0.0369(4) Uani 1 1 d . . .
H26 H 0.3498 -0.1443 0.1995 0.044 Uiso 1 1 calc R . .
C27 C 0.29863(19) 0.46921(16) 0.03926(16) 0.0443(4) Uani 1 1 d . . .
C28 C 0.2748(3) 0.57916(17) 0.08148(19) 0.0587(5) Uani 1 1 d . . .
H28A H 0.3317 0.6334 0.0353 0.088 Uiso 1 1 calc R . .
H28B H 0.2955 0.5706 0.1563 0.088 Uiso 1 1 calc R . .
H28C H 0.1807 0.6083 0.0816 0.088 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
Cl1 Si 2.1557(8) . ?
Cl2 Si 2.1631(8) . ?
S1 C1 1.7181(15) . ?
S1 Si 2.2627(7) . ?
S2 C1 1.7050(14) . ?
S2 Si 2.3396(7) . ?
S3 C14 1.7213(16) . ?
S3 Si 2.2843(7) . ?
S4 C14 1.7071(14) . ?
S4 Si 2.3489(8) . ?
N1 C1 1.3350(17) . ?
N1 C8 1.4516(18) . ?
N1 C2 1.4528(17) . ?
N2 C14 1.3296(19) . ?
N2 C21 1.4529(19) . ?
N2 C15 1.4530(18) . ?
N3 C27 1.135(3) . ?
C2 C3 1.375(2) . ?
C2 C7 1.385(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.377(3) . ?
C5 C6 1.374(3) . ?
C6 C7 1.390(2) . ?
C8 C9 1.383(2) . ?
C8 C13 1.388(2) . ?
C9 C10 1.394(2) . ?
C10 C11 1.385(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.387(2) . ?
C15 C16 1.384(2) . ?
C15 C20 1.390(2) . ?
C16 C17 1.395(2) . ?
C17 C18 1.380(3) . ?
C18 C19 1.381(3) . ?
C19 C20 1.388(2) . ?
C21 C22 1.374(2) . ?
C21 C26 1.386(2) . ?
C22 C23 1.395(2) . ?
C23 C24 1.381(2) . ?
C24 C25 1.381(3) . ?
C25 C26 1.387(3) . ?
C27 C28 1.440(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
C1 S1 Si 85.86(5) . . ?
C1 S2 Si 83.73(5) . . ?
C14 S3 Si 85.28(5) . . ?
C14 S4 Si 83.57(6) . . ?
Cl1 Si Cl2 92.15(3) . . ?
Cl1 Si S1 92.83(3) . . ?
Cl2 Si S1 98.42(3) . . ?
Cl1 Si S3 100.65(3) . . ?
Cl2 Si S3 92.21(3) . . ?
S1 Si S3 162.51(2) . . ?
Cl1 Si S2 169.55(2) . . ?
Cl2 Si S2 90.92(3) . . ?
S1 Si S2 76.84(2) . . ?
S3 Si S2 89.21(3) . . ?
Cl1 Si S4 90.67(3) . . ?
Cl2 Si S4 168.95(2) . . ?
S1 Si S4 92.10(3) . . ?
S3 Si S4 76.77(3) . . ?
S2 Si S4 88.19(3) . . ?
C1 N1 C8 122.48(11) . . ?
C1 N1 C2 119.79(11) . . ?
C8 N1 C2 117.73(10) . . ?
C14 N2 C21 120.20(12) . . ?
C14 N2 C15 122.72(12) . . ?
C21 N2 C15 116.63(11) . . ?
N1 C1 S2 124.97(11) . . ?
N1 C1 S1 121.65(10) . . ?
S2 C1 S1 113.37(8) . . ?
C3 C2 C7 121.13(14) . . ?
C3 C2 N1 119.02(13) . . ?
C7 C2 N1 119.84(13) . . ?
C2 C3 C4 119.03(15) . . ?
C5 C4 C3 120.40(16) . . ?
C6 C5 C4 120.14(15) . . ?
C5 C6 C7 120.27(17) . . ?
C2 C7 C6 118.99(16) . . ?
C9 C8 C13 121.10(14) . . ?
C9 C8 N1 120.00(12) . . ?
C13 C8 N1 118.88(14) . . ?
C8 C9 C10 119.14(15) . . ?
C11 C10 C9 120.08(17) . . ?
C12 C11 C10 120.12(15) . . ?
C11 C12 C13 120.47(15) . . ?
C12 C13 C8 119.07(16) . . ?
N2 C14 S4 122.93(11) . . ?
N2 C14 S3 122.93(11) . . ?
S4 C14 S3 114.13(8) . . ?
C16 C15 C20 121.30(14) . . ?
C16 C15 N2 119.55(14) . . ?
C20 C15 N2 118.97(13) . . ?
C15 C16 C17 118.60(16) . . ?
C18 C17 C16 120.49(16) . . ?
C17 C18 C19 120.38(15) . . ?
C18 C19 C20 120.04(16) . . ?
C19 C20 C15 119.17(15) . . ?
C22 C21 C26 121.54(15) . . ?
C22 C21 N2 119.65(13) . . ?
C26 C21 N2 118.76(14) . . ?
C21 C22 C23 119.01(14) . . ?
C24 C23 C22 120.02(16) . . ?
C25 C24 C23 120.30(16) . . ?
C24 C25 C26 120.24(15) . . ?
C21 C26 C25 118.87(16) . . ?
N3 C27 C28 179.5(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
C1 S1 Si Cl1 -175.64(5) . . . . ?
C1 S1 Si Cl2 91.76(5) . . . . ?
C1 S1 Si S3 -35.07(9) . . . . ?
C1 S1 Si S2 2.79(5) . . . . ?
C1 S1 Si S4 -84.86(5) . . . . ?
C14 S3 Si Cl1 91.24(5) . . . . ?
C14 S3 Si Cl2 -176.15(5) . . . . ?
C14 S3 Si S1 -48.56(9) . . . . ?
C14 S3 Si S2 -85.26(5) . . . . ?
C14 S3 Si S4 3.06(5) . . . . ?
C1 S2 Si Cl1 5.88(14) . . . . ?
C1 S2 Si Cl2 -101.25(5) . . . . ?
C1 S2 Si S1 -2.82(5) . . . . ?
C1 S2 Si S3 166.55(5) . . . . ?
C1 S2 Si S4 89.76(5) . . . . ?
C14 S4 Si Cl1 -103.88(5) . . . . ?
C14 S4 Si Cl2 0.98(13) . . . . ?
C14 S4 Si S1 163.27(5) . . . . ?
C14 S4 Si S3 -3.10(5) . . . . ?
C14 S4 Si S2 86.51(5) . . . . ?
C8 N1 C1 S2 -2.8(2) . . . . ?
C2 N1 C1 S2 177.68(11) . . . . ?
C8 N1 C1 S1 178.49(11) . . . . ?
C2 N1 C1 S1 -1.03(19) . . . . ?
Si S2 C1 N1 -174.86(13) . . . . ?
Si S2 C1 S1 3.94(7) . . . . ?
Si S1 C1 N1 174.79(12) . . . . ?
Si S1 C1 S2 -4.06(7) . . . . ?
C1 N1 C2 C3 88.39(17) . . . . ?
C8 N1 C2 C3 -91.15(16) . . . . ?
C1 N1 C2 C7 -92.97(17) . . . . ?
C8 N1 C2 C7 87.48(17) . . . . ?
C7 C2 C3 C4 0.6(2) . . . . ?
N1 C2 C3 C4 179.23(13) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C3 C2 C7 C6 1.2(2) . . . . ?
N1 C2 C7 C6 -177.43(15) . . . . ?
C5 C6 C7 C2 -2.0(3) . . . . ?
C1 N1 C8 C9 -57.2(2) . . . . ?
C2 N1 C8 C9 122.36(14) . . . . ?
C1 N1 C8 C13 124.65(15) . . . . ?
C2 N1 C8 C13 -55.82(18) . . . . ?
C13 C8 C9 C10 -1.0(2) . . . . ?
N1 C8 C9 C10 -179.13(13) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 1.5(2) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
C11 C12 C13 C8 0.3(2) . . . . ?
C9 C8 C13 C12 0.9(2) . . . . ?
N1 C8 C13 C12 179.09(13) . . . . ?
C21 N2 C14 S4 1.57(19) . . . . ?
C15 N2 C14 S4 173.62(10) . . . . ?
C21 N2 C14 S3 -178.97(10) . . . . ?
C15 N2 C14 S3 -6.93(19) . . . . ?
Si S4 C14 N2 -176.11(12) . . . . ?
Si S4 C14 S3 4.39(7) . . . . ?
Si S3 C14 N2 176.00(12) . . . . ?
Si S3 C14 S4 -4.50(7) . . . . ?
C14 N2 C15 C16 108.18(17) . . . . ?
C21 N2 C15 C16 -79.51(17) . . . . ?
C14 N2 C15 C20 -76.75(18) . . . . ?
C21 N2 C15 C20 95.56(17) . . . . ?
C20 C15 C16 C17 -1.2(3) . . . . ?
N2 C15 C16 C17 173.79(15) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C18 C19 C20 C15 0.0(2) . . . . ?
C16 C15 C20 C19 1.2(2) . . . . ?
N2 C15 C20 C19 -173.82(14) . . . . ?
C14 N2 C21 C22 -99.62(17) . . . . ?
C15 N2 C21 C22 87.87(16) . . . . ?
C14 N2 C21 C26 82.94(18) . . . . ?
C15 N2 C21 C26 -89.58(16) . . . . ?
C26 C21 C22 C23 -0.1(2) . . . . ?
N2 C21 C22 C23 -177.49(13) . . . . ?
C21 C22 C23 C24 -1.1(2) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C22 C21 C26 C25 1.5(2) . . . . ?
N2 C21 C26 C25 178.91(14) . . . . ?
C24 C25 C26 C21 -1.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.930
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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__compound4__BAU21D
_database_code_depnum_ccdc_archive 'CCDC 1499675'
_audit_update_record             
;
2016-08-18 deposited with the CCDC.
2016-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H28 Cl2 N2 S4 Si, C2 H3 N'
_chemical_formula_sum            'C16 H31 Cl2 N3 S4 Si'
_chemical_formula_weight         492.67

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.825(6)
_cell_length_b                   19.594(15)
_cell_length_c                   13.142(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.87(4)
_cell_angle_gamma                90
_cell_volume                     2506(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9850
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.86

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.445
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.343
_exptl_absorpt_coefficient_mu    0.647
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7616
_exptl_absorpt_correction_T_max  0.8085
_exptl_absorpt_process_details   'Sadabs 2008/1 (Bruker 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32227
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.435
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4936
_reflns_number_gt                4507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP & POV-Ray'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+2.8714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4936
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.94683(4) 0.71719(2) 1.02429(3) 0.02184(11) Uani 1 1 d . . . . .
S1 S 0.87183(4) 0.63509(2) 0.79900(3) 0.01728(10) Uani 1 1 d . . . . .
Cl1 Cl 0.86963(5) 0.79713(2) 0.82034(4) 0.02181(11) Uani 1 1 d . . . . .
S2 S 0.70540(5) 0.60943(2) 0.95579(4) 0.02095(11) Uani 1 1 d . . . . .
S3 S 0.63943(4) 0.77281(2) 0.98571(3) 0.01741(11) Uani 1 1 d . . . . .
Si Si 0.78162(5) 0.71288(2) 0.89737(4) 0.01317(11) Uani 1 1 d . . . . .
N1 N 0.79608(19) 0.50778(8) 0.84034(14) 0.0282(4) Uani 1 1 d . . . . .
N2 N 0.38549(15) 0.78185(8) 0.87372(11) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.79030(18) 0.57327(9) 0.86337(14) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.7180(3) 0.45401(12) 0.8865(2) 0.0520(7) Uani 1 1 d . . . . .
H2 H 0.7381 0.4107 0.8512 0.062 Uiso 1 1 calc R U . . .
C3 C 0.5660(3) 0.46335(18) 0.8638(3) 0.0710(11) Uani 1 1 d . . . . .
H3A H 0.5197 0.4233 0.8876 0.106 Uiso 1 1 calc R U . . .
H3B H 0.5395 0.4688 0.7897 0.106 Uiso 1 1 calc R U . . .
H3C H 0.5390 0.5041 0.8994 0.106 Uiso 1 1 calc R U . . .
C4 C 0.7739(5) 0.44317(14) 1.0009(2) 0.0739(11) Uani 1 1 d . . . . .
H4A H 0.7564 0.4841 1.0400 0.111 Uiso 1 1 calc R U . . .
H4B H 0.8731 0.4346 1.0080 0.111 Uiso 1 1 calc R U . . .
H4C H 0.7279 0.4039 1.0273 0.111 Uiso 1 1 calc R U . . .
S4 S 0.58116(4) 0.72010(2) 0.78270(3) 0.01655(10) Uani 1 1 d . . . . .
C5 C 0.8774(2) 0.48539(11) 0.75649(18) 0.0346(5) Uani 1 1 d . . . . .
H5 H 0.9371 0.5245 0.7419 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7809(3) 0.47106(12) 0.65974(18) 0.0378(5) Uani 1 1 d . . . . .
H6A H 0.7223 0.4320 0.6710 0.057 Uiso 1 1 calc R U . . .
H6B H 0.8341 0.4606 0.6039 0.057 Uiso 1 1 calc R U . . .
H6C H 0.7234 0.5113 0.6414 0.057 Uiso 1 1 calc R U . . .
C7 C 0.9710(3) 0.42549(15) 0.7894(2) 0.0598(8) Uani 1 1 d . . . . .
H7A H 1.0275 0.4362 0.8548 0.090 Uiso 1 1 calc R U . . .
H7B H 1.0306 0.4166 0.7369 0.090 Uiso 1 1 calc R U . . .
H7C H 0.9152 0.3849 0.7978 0.090 Uiso 1 1 calc R U . . .
C8 C 0.51452(18) 0.76196(9) 0.87997(13) 0.0147(3) Uani 1 1 d . . . . .
C9 C 0.29094(19) 0.76968(10) 0.77594(14) 0.0212(4) Uani 1 1 d . . . . .
H9 H 0.3497 0.7599 0.7213 0.025 Uiso 1 1 calc R U . . .
C10 C 0.2053(2) 0.70620(11) 0.78738(16) 0.0268(4) Uani 1 1 d . . . . .
H10A H 0.2663 0.6671 0.8048 0.040 Uiso 1 1 calc R U . . .
H10B H 0.1460 0.6971 0.7226 0.040 Uiso 1 1 calc R U . . .
H10C H 0.1484 0.7134 0.8421 0.040 Uiso 1 1 calc R U . . .
C11 C 0.2050(2) 0.83204(11) 0.74187(15) 0.0254(4) Uani 1 1 d . . . . .
H11A H 0.1388 0.8402 0.7899 0.038 Uiso 1 1 calc R U . . .
H11B H 0.1557 0.8243 0.6729 0.038 Uiso 1 1 calc R U . . .
H11C H 0.2652 0.8719 0.7408 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3217(2) 0.80850(11) 0.96314(15) 0.0250(4) Uani 1 1 d . . . . .
H12 H 0.2218 0.8143 0.9376 0.030 Uiso 1 1 calc R U . . .
C13 C 0.3292(2) 0.75765(12) 1.05138(15) 0.0281(4) Uani 1 1 d . . . . .
H13A H 0.4242 0.7542 1.0851 0.042 Uiso 1 1 calc R U . . .
H13B H 0.2978 0.7128 1.0246 0.042 Uiso 1 1 calc R U . . .
H13C H 0.2702 0.7732 1.1012 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3749(3) 0.87915(11) 0.99497(18) 0.0357(5) Uani 1 1 d . . . . .
H14A H 0.3244 0.8969 1.0486 0.054 Uiso 1 1 calc R U . . .
H14B H 0.3618 0.9097 0.9353 0.054 Uiso 1 1 calc R U . . .
H14C H 0.4730 0.8764 1.0216 0.054 Uiso 1 1 calc R U . . .
N3 N 0.2003(6) 0.5322(2) 0.6579(4) 0.0967(15) Uani 0.757(4) 1 d . . P A 1
C15 C 0.2890(5) 0.55641(19) 0.6302(3) 0.0515(10) Uani 0.757(4) 1 d . . P A 1
C16 C 0.4011(5) 0.5943(2) 0.5893(3) 0.0558(12) Uani 0.757(4) 1 d . . P A 1
H16A H 0.4707 0.5619 0.5725 0.084 Uiso 0.757(4) 1 calc R U P A 1
H16B H 0.4432 0.6266 0.6413 0.084 Uiso 0.757(4) 1 calc R U P A 1
H16C H 0.3631 0.6192 0.5273 0.084 Uiso 0.757(4) 1 calc R U P A 1
N3B N 0.3838(17) 0.4833(7) 0.6103(12) 0.0967(15) Uani 0.243(4) 1 d . . P A 2
C15B C 0.4059(13) 0.5399(6) 0.5953(10) 0.060(4) Uani 0.243(4) 1 d . . P A 2
C16B C 0.4670(15) 0.5986(8) 0.5588(12) 0.0558(12) Uani 0.243(4) 1 d . . P A 2
H16D H 0.5364 0.5848 0.5159 0.084 Uiso 0.243(4) 1 calc R U P A 2
H16E H 0.5107 0.6254 0.6172 0.084 Uiso 0.243(4) 1 calc R U P A 2
H16F H 0.3963 0.6262 0.5180 0.084 Uiso 0.243(4) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 Si 2.1639(14) . ?
S1 C1 1.735(2) . ?
S1 Si 2.2571(12) . ?
Cl1 Si 2.1765(12) . ?
S2 C1 1.718(2) . ?
S2 Si 2.3275(15) . ?
S3 C8 1.736(2) . ?
S3 Si 2.2633(12) . ?
Si S4 2.3146(15) . ?
N1 C1 1.321(3) . ?
N1 C2 1.481(3) . ?
N1 C5 1.512(3) . ?
N2 C8 1.318(2) . ?
N2 C9 1.498(2) . ?
N2 C12 1.499(2) . ?
C2 C3 1.493(5) . ?
C2 C4 1.543(4) . ?
S4 C8 1.7219(19) . ?
C5 C6 1.505(3) . ?
C5 C7 1.517(3) . ?
C9 C11 1.517(3) . ?
C9 C10 1.521(3) . ?
C12 C14 1.518(3) . ?
C12 C13 1.523(3) . ?
N3 C15 1.097(6) . ?
C15 C16 1.488(6) . ?
N3B C15B 1.151(17) . ?
C15B C16B 1.411(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 Si 87.05(8) . . ?
C1 S2 Si 85.22(8) . . ?
C8 S3 Si 86.80(8) . . ?
Cl2 Si Cl1 91.44(4) . . ?
Cl2 Si S1 98.97(5) . . ?
Cl1 Si S1 91.93(6) . . ?
Cl2 Si S3 92.00(5) . . ?
Cl1 Si S3 99.06(6) . . ?
S1 Si S3 164.28(3) . . ?
Cl2 Si S4 168.84(3) . . ?
Cl1 Si S4 90.44(4) . . ?
S1 Si S4 91.96(4) . . ?
S3 Si S4 76.84(5) . . ?
Cl2 Si S2 91.20(4) . . ?
Cl1 Si S2 168.60(3) . . ?
S1 Si S2 76.71(5) . . ?
S3 Si S2 91.93(5) . . ?
S4 Si S2 89.11(3) . . ?
C1 N1 C2 123.8(2) . . ?
C1 N1 C5 119.49(18) . . ?
C2 N1 C5 116.56(18) . . ?
C8 N2 C9 118.98(15) . . ?
C8 N2 C12 123.75(16) . . ?
C9 N2 C12 116.83(15) . . ?
N1 C1 S2 127.07(16) . . ?
N1 C1 S1 121.94(16) . . ?
S2 C1 S1 110.99(11) . . ?
N1 C2 C3 113.0(2) . . ?
N1 C2 C4 111.2(2) . . ?
C3 C2 C4 115.1(3) . . ?
C8 S4 Si 85.51(8) . . ?
C6 C5 N1 109.6(2) . . ?
C6 C5 C7 112.6(2) . . ?
N1 C5 C7 112.1(2) . . ?
N2 C8 S4 123.70(14) . . ?
N2 C8 S3 125.59(14) . . ?
S4 C8 S3 110.71(11) . . ?
N2 C9 C11 112.29(16) . . ?
N2 C9 C10 109.39(15) . . ?
C11 C9 C10 113.26(17) . . ?
N2 C12 C14 111.63(17) . . ?
N2 C12 C13 112.80(17) . . ?
C14 C12 C13 114.07(18) . . ?
N3 C15 C16 175.0(5) . . ?
N3B C15B C16B 160.3(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
C2 N1 C1 S2 5.4(3) . . . . ?
C5 N1 C1 S2 -179.54(15) . . . . ?
C2 N1 C1 S1 -174.19(18) . . . . ?
C5 N1 C1 S1 0.8(3) . . . . ?
Si S2 C1 N1 -177.89(17) . . . . ?
Si S2 C1 S1 1.79(8) . . . . ?
Si S1 C1 N1 177.86(16) . . . . ?
Si S1 C1 S2 -1.84(9) . . . . ?
C1 N1 C2 C3 61.6(3) . . . . ?
C5 N1 C2 C3 -113.6(2) . . . . ?
C1 N1 C2 C4 -69.6(3) . . . . ?
C5 N1 C2 C4 115.2(2) . . . . ?
C1 N1 C5 C6 -101.8(2) . . . . ?
C2 N1 C5 C6 73.6(3) . . . . ?
C1 N1 C5 C7 132.4(2) . . . . ?
C2 N1 C5 C7 -52.2(3) . . . . ?
C9 N2 C8 S4 -1.9(2) . . . . ?
C12 N2 C8 S4 170.25(14) . . . . ?
C9 N2 C8 S3 178.94(13) . . . . ?
C12 N2 C8 S3 -8.9(3) . . . . ?
Si S4 C8 N2 -176.02(16) . . . . ?
Si S4 C8 S3 3.23(8) . . . . ?
Si S3 C8 N2 175.93(16) . . . . ?
Si S3 C8 S4 -3.30(8) . . . . ?
C8 N2 C9 C11 -134.18(17) . . . . ?
C12 N2 C9 C11 53.1(2) . . . . ?
C8 N2 C9 C10 99.2(2) . . . . ?
C12 N2 C9 C10 -73.5(2) . . . . ?
C8 N2 C12 C14 71.6(2) . . . . ?
C9 N2 C12 C14 -116.09(19) . . . . ?
C8 N2 C12 C13 -58.4(2) . . . . ?
C9 N2 C12 C13 113.92(19) . . . . ?

_refine_diff_density_max         0.843
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.056

