# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1851929'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
'Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science'
_audit_update_record             
;
2021-04-16 deposited with the CCDC.	2021-04-21 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C15 H20 N2 O4 S Si'
_chemical_formula_sum            'C15 H20 N2 O4 S Si'
_chemical_formula_weight         352.49
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Si 0.08192 0.07060 6.29150 3.03530 1.98910 1.54100 2.43860 32.33370 0.67850
81.69370 1.14069998264
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.937(8)
_cell_length_b                   7.336(4)
_cell_length_c                   15.771(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.94(3)
_cell_angle_gamma                90
_cell_volume                     1603.7(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.59
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0919 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.9471.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.4598
_exptl_crystal_description       prism
_exptl_crystal_F_000             745.1559
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.138
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            49417
_diffrn_reflns_theta_full        27.9972
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.60
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -18
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -12
_reflns_number_gt                3472
_reflns_number_total             3854
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.3560
_refine_diff_density_min         -0.2854
_refine_diff_density_rms         0.0580
_refine_ls_d_res_high            0.7570
_refine_ls_d_res_low             7.8431
_refine_ls_goodness_of_fit_ref   1.0563
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.0563
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.9123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0772
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C15(H15a,H15b), C14(H14a,H14b), C2(H2a,H2b), C5(H5a,H5b), C4(H4a,
 H4b), C6(H6a,H6b), C3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
S1 S 0.81029(2) 0.17076(5) 0.37071(2) 0.01923(9) Uani 1.000000 .
Si1 Si 0.67035(2) 0.27663(4) 0.61061(2) 0.01284(9) Uani 1.000000 .
O1 O 0.62939(6) 0.46679(12) 0.56104(6) 0.01798(19) Uani 1.000000 .
O2 O 0.60615(6) 0.08543(12) 0.59310(6) 0.01830(19) Uani 1.000000 .
O3 O 0.74706(6) 0.29567(13) 0.69880(5) 0.01752(19) Uani 1.000000 .
O4 O 0.78260(6) 0.16898(13) 0.20356(6) 0.01964(19) Uani 1.000000 .
N2 N 0.64226(7) 0.18851(15) 0.26459(7) 0.0173(2) Uani 1.000000 .
N1 N 0.56334(7) 0.33903(14) 0.69476(6) 0.0145(2) Uani 1.000000 .
C1 C 0.56418(9) 0.58675(17) 0.59690(8) 0.0174(2) Uani 1.000000 .
H1a H 0.59982(9) 0.67595(17) 0.63302(8) 0.0209(3) Uiso 1.000000 R
H1b H 0.52533(9) 0.65114(17) 0.55187(8) 0.0209(3) Uiso 1.000000 R
C15 C 0.76430(8) 0.22253(17) 0.53577(8) 0.0164(2) Uani 1.000000 .
H15a H 0.81166(8) 0.31980(17) 0.53831(8) 0.0196(3) Uiso 1.000000 R
H15b H 0.79743(8) 0.11072(17) 0.55396(8) 0.0196(3) Uiso 1.000000 R
C14 C 0.71866(9) 0.20095(19) 0.44441(8) 0.0199(3) Uani 1.000000 .
H14a H 0.68033(9) 0.30809(19) 0.42810(8) 0.0239(3) Uiso 1.000000 R
H14b H 0.67598(9) 0.09618(19) 0.44082(8) 0.0239(3) Uiso 1.000000 R
C7 C 0.73563(9) 0.17599(17) 0.27624(8) 0.0166(2) Uani 1.000000 .
C8 C 0.62202(9) 0.19343(17) 0.17534(8) 0.0168(2) Uani 1.000000 .
C10 C 0.53504(10) 0.2099(2) 0.12450(9) 0.0229(3) Uani 1.000000 .
H10 H 0.47660(10) 0.2181(2) 0.14787(9) 0.0275(3) Uiso 1.000000 R
C11 C 0.53965(11) 0.2134(2) 0.03682(9) 0.0273(3) Uani 1.000000 .
H11 H 0.48291(11) 0.2254(2) 0.00066(9) 0.0328(4) Uiso 1.000000 R
C12 C 0.62717(11) 0.1995(2) 0.00178(9) 0.0273(3) Uani 1.000000 .
H12 H 0.62692(11) 0.2014(2) -0.05721(9) 0.0328(4) Uiso 1.000000 R
C13 C 0.71473(10) 0.18294(19) 0.05189(9) 0.0232(3) Uani 1.000000 .
H13 H 0.77328(10) 0.17362(19) 0.02878(9) 0.0279(3) Uiso 1.000000 R
C9 C 0.70817(9) 0.18137(17) 0.13842(8) 0.0175(2) Uani 1.000000 .
C2 C 0.51411(9) 0.06279(18) 0.62366(9) 0.0205(3) Uani 1.000000 .
H2a H 0.46397(9) 0.11165(18) 0.58268(9) 0.0246(3) Uiso 1.000000 R
H2b H 0.50120(9) -0.06565(18) 0.63171(9) 0.0246(3) Uiso 1.000000 R
C5 C 0.51501(9) 0.16343(17) 0.70779(9) 0.0194(3) Uani 1.000000 .
H5a H 0.55032(9) 0.09465(17) 0.75339(9) 0.0233(3) Uiso 1.000000 R
H5b H 0.44977(9) 0.18330(17) 0.72206(9) 0.0233(3) Uiso 1.000000 R
C4 C 0.49959(8) 0.47527(17) 0.64904(8) 0.0165(2) Uani 1.000000 .
H4a H 0.44898(8) 0.41583(17) 0.61217(8) 0.0198(3) Uiso 1.000000 R
H4b H 0.47010(8) 0.55248(17) 0.68903(8) 0.0198(3) Uiso 1.000000 R
C6 C 0.61821(9) 0.41098(18) 0.77243(8) 0.0184(2) Uani 1.000000 .
H6a H 0.62866(9) 0.54104(18) 0.76716(8) 0.0220(3) Uiso 1.000000 R
H6b H 0.58364(9) 0.38942(18) 0.82180(8) 0.0220(3) Uiso 1.000000 R
C3 C 0.71384(9) 0.30967(19) 0.78121(8) 0.0197(3) Uani 1.000000 .
H3a H 0.70548(9) 0.18902(19) 0.80451(8) 0.0236(3) Uiso 1.000000 R
H3b H 0.76070(9) 0.37514(19) 0.81954(8) 0.0236(3) Uiso 1.000000 R


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
S1 C14 1.8270(14) . ?
S1 C7 1.7271(15) . ?
Si1 O1 1.6705(12) . ?
Si1 O2 1.6712(12) . ?
Si1 O3 1.6700(12) . ?
Si1 N1 2.1457(13) . ?
Si1 C15 1.8935(14) . ?
O1 C1 1.4236(15) . ?
O2 C2 1.4260(16) . ?
O3 C3 1.4277(16) . ?
O4 C7 1.3785(15) . ?
O4 C9 1.3853(16) . ?
N2 C7 1.2985(17) . ?
N2 C8 1.4071(17) . ?
N1 C5 1.4778(17) . ?
N1 C4 1.4749(16) . ?
N1 C6 1.4731(16) . ?
C1 H1a 0.9700 . ?
C1 H1b 0.9700 . ?
C1 C4 1.5195(18) . ?
C15 H15a 0.9700 . ?
C15 H15b 0.9700 . ?
C15 C14 1.5217(18) . ?
C14 H14a 0.9700 . ?
C14 H14b 0.9700 . ?
C8 C10 1.3878(19) . ?
C8 C9 1.3904(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9300 . ?
C13 C9 1.3772(19) . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C2 C5 1.5173(19) . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C6 C3 1.5198(18) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?

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
C7 S1 C14 98.50(6) . . ?
O2 Si1 O1 118.19(5) . . ?
O3 Si1 O1 118.57(5) . . ?
O3 Si1 O2 119.57(5) . . ?
N1 Si1 O1 83.43(4) . . ?
N1 Si1 O2 83.50(4) . . ?
N1 Si1 O3 83.87(4) . . ?
C15 Si1 O1 96.21(5) . . ?
C15 Si1 O2 96.54(5) . . ?
C15 Si1 O3 96.44(5) . . ?
C15 Si1 N1 179.61(5) . . ?
C1 O1 Si1 122.11(8) . . ?
C2 O2 Si1 121.79(8) . . ?
C3 O3 Si1 121.61(8) . . ?
C9 O4 C7 103.34(9) . . ?
C8 N2 C7 103.74(10) . . ?
C5 N1 Si1 104.83(7) . . ?
C4 N1 Si1 105.33(7) . . ?
C4 N1 C5 113.48(10) . . ?
C6 N1 Si1 104.86(7) . . ?
C6 N1 C5 113.68(10) . . ?
C6 N1 C4 113.47(10) . . ?
H1a C1 O1 109.95(6) . . ?
H1b C1 O1 109.95(6) . . ?
H1b C1 H1a 108.3 . . ?
C4 C1 O1 108.70(10) . . ?
C4 C1 H1a 109.95(7) . . ?
C4 C1 H1b 109.95(6) . . ?
H15a C15 Si1 109.36(4) . . ?
H15b C15 Si1 109.36(4) . . ?
H15b C15 H15a 108.0 . . ?
C14 C15 Si1 111.33(8) . . ?
C14 C15 H15a 109.36(7) . . ?
C14 C15 H15b 109.36(7) . . ?
C15 C14 S1 111.33(8) . . ?
H14a C14 S1 109.36(5) . . ?
H14a C14 C15 109.36(7) . . ?
H14b C14 S1 109.36(4) . . ?
H14b C14 C15 109.36(7) . . ?
H14b C14 H14a 108.0 . . ?
O4 C7 S1 114.89(9) . . ?
N2 C7 S1 128.98(10) . . ?
N2 C7 O4 116.11(11) . . ?
C10 C8 N2 130.76(11) . . ?
C9 C8 N2 108.96(11) . . ?
C9 C8 C10 120.27(12) . . ?
H10 C10 C8 121.68(8) . . ?
C11 C10 C8 116.65(12) . . ?
C11 C10 H10 121.68(8) . . ?
H11 C11 C10 119.17(8) . . ?
C12 C11 C10 121.67(13) . . ?
C12 C11 H11 119.17(8) . . ?
H12 C12 C11 118.85(8) . . ?
C13 C12 C11 122.29(13) . . ?
C13 C12 H12 118.85(8) . . ?
H13 C13 C12 122.58(8) . . ?
C9 C13 C12 114.84(12) . . ?
C9 C13 H13 122.58(8) . . ?
C8 C9 O4 107.84(11) . . ?
C13 C9 O4 127.89(11) . . ?
C13 C9 C8 124.28(12) . . ?
H2a C2 O2 110.06(7) . . ?
H2b C2 O2 110.06(6) . . ?
H2b C2 H2a 108.4 . . ?
C5 C2 O2 108.21(10) . . ?
C5 C2 H2a 110.06(7) . . ?
C5 C2 H2b 110.06(7) . . ?
C2 C5 N1 105.38(10) . . ?
H5a C5 N1 110.67(7) . . ?
H5a C5 C2 110.67(7) . . ?
H5b C5 N1 110.67(6) . . ?
H5b C5 C2 110.67(7) . . ?
H5b C5 H5a 108.8 . . ?
C1 C4 N1 105.58(9) . . ?
H4a C4 N1 110.62(6) . . ?
H4a C4 C1 110.62(7) . . ?
H4b C4 N1 110.62(6) . . ?
H4b C4 C1 110.62(7) . . ?
H4b C4 H4a 108.8 . . ?
H6a C6 N1 110.54(7) . . ?
H6b C6 N1 110.54(6) . . ?
H6b C6 H6a 108.7 . . ?
C3 C6 N1 105.99(10) . . ?
C3 C6 H6a 110.54(7) . . ?
C3 C6 H6b 110.54(7) . . ?
C6 C3 O3 108.43(10) . . ?
H3a C3 O3 110.01(7) . . ?
H3a C3 C6 110.01(7) . . ?
H3b C3 O3 110.01(6) . . ?
H3b C3 C6 110.01(7) . . ?
H3b C3 H3a 108.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1851930'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
'Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science'
_audit_update_record             
;
2021-04-16 deposited with the CCDC.	2021-04-21 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H20 N2 O3 S2 Si'
_chemical_formula_sum            'C15 H20 N2 O3 S2 Si'
_chemical_formula_weight         368.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.187(5)
_cell_length_b                   10.587(4)
_cell_length_c                   13.213(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.361(16)
_cell_angle_gamma                90.00
_cell_volume                     1638.4(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      3.09
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0902 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.8956.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombohedron
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.337
_exptl_crystal_size_min          0.239
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47504
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.59
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker APEX2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                3715
_reflns_number_total             3929
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0288P)²+1.0236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0638
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C3(H3A,H3B), C6(H6A,H6B), C5(H5A,H5B), C2(H2A,
 H2B), C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.71459(2) 0.27595(2) 0.58272(2) 0.01345(7) Uani 1 d . . .
S2 S 0.81309(2) 0.09989(2) 0.47447(2) 0.01331(7) Uani 1 d . . .
Si1 Si 0.63772(2) 0.65632(3) 0.67975(2) 0.00890(7) Uani 1 d . . .
O3 O 0.51996(7) 0.65125(7) 0.69703(7) 0.01360(16) Uani 1 d . . .
O2 O 0.63291(7) 0.71716(7) 0.56035(7) 0.01432(16) Uani 1 d . . .
O1 O 0.76489(7) 0.64979(7) 0.79533(7) 0.01563(17) Uani 1 d . . .
N2 N 0.84317(8) 0.34448(9) 0.47975(8) 0.01348(18) Uani 1 d . . .
N1 N 0.64161(8) 0.84851(8) 0.72694(8) 0.01182(18) Uani 1 d . . .
C11 C 1.01163(10) 0.29649(12) 0.32155(10) 0.0188(2) Uani 1 d . . .
H11 H 1.0523 0.3412 0.2916 0.023 Uiso 1 calc . . R
C10 C 0.95983(10) 0.36122(11) 0.37692(10) 0.0164(2) Uani 1 d . . .
H10 H 0.9656 0.4486 0.3843 0.020 Uiso 1 calc . . R
C8 C 0.89870(9) 0.29241(10) 0.42140(9) 0.0126(2) Uani 1 d . . .
C7 C 0.79581(9) 0.25535(10) 0.51126(9) 0.01192(19) Uani 1 d . . .
C14 C 0.70418(9) 0.44758(10) 0.58240(9) 0.0131(2) Uani 1 d . . .
H14A H 0.7798 0.4845 0.6222 0.016 Uiso 1 calc . . R
H14B H 0.6683 0.4789 0.5047 0.016 Uiso 1 calc . . R
C15 C 0.63285(9) 0.48347(10) 0.64187(9) 0.01129(19) Uani 1 d . . .
H15A H 0.6589 0.4341 0.7112 0.014 Uiso 1 calc . . R
H15B H 0.5541 0.4603 0.5928 0.014 Uiso 1 calc . . R
C3 C 0.48040(9) 0.75636(10) 0.73587(10) 0.0141(2) Uani 1 d . . .
H3A H 0.5088 0.7514 0.8177 0.017 Uiso 1 calc . . R
H3B H 0.3976 0.7564 0.7001 0.017 Uiso 1 calc . . R
C6 C 0.52332(10) 0.87658(11) 0.70518(10) 0.0155(2) Uani 1 d . . .
H6A H 0.4761 0.8981 0.6257 0.019 Uiso 1 calc . . R
H6B H 0.5223 0.9466 0.7521 0.019 Uiso 1 calc . . R
C5 C 0.67691(10) 0.91909(10) 0.65206(10) 0.0163(2) Uani 1 d . . .
H5A H 0.7595 0.9209 0.6844 0.020 Uiso 1 calc . . R
H5B H 0.6489 1.0053 0.6420 0.020 Uiso 1 calc . . R
C2 C 0.62467(11) 0.84898(10) 0.53861(10) 0.0169(2) Uani 1 d . . .
H2A H 0.5452 0.8730 0.4943 0.020 Uiso 1 calc . . R
H2B H 0.6650 0.8707 0.4954 0.020 Uiso 1 calc . . R
C1 C 0.81735(10) 0.75664(11) 0.86480(10) 0.0171(2) Uani 1 d . . .
H1A H 0.8723 0.7934 0.8436 0.021 Uiso 1 calc . . R
H1B H 0.8575 0.7313 0.9441 0.021 Uiso 1 calc . . R
C4 C 0.72564(10) 0.85366(11) 0.84892(9) 0.0160(2) Uani 1 d . . .
H4A H 0.6896 0.8328 0.8963 0.019 Uiso 1 calc . . R
H4B H 0.7586 0.9375 0.8692 0.019 Uiso 1 calc . . R
C9 C 0.89212(9) 0.15997(10) 0.40997(9) 0.0121(2) Uani 1 d . . .
C13 C 0.94422(9) 0.09470(11) 0.35480(10) 0.0157(2) Uani 1 d . . .
H13 H 0.9395 0.0072 0.3480 0.019 Uiso 1 calc . . R
C12 C 1.00345(10) 0.16500(12) 0.31028(10) 0.0183(2) Uani 1 d . . .
H12 H 1.0383 0.1238 0.2723 0.022 Uiso 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
S1 C7 1.7367(12) . ?
S1 C14 1.8220(13) . ?
S2 C7 1.7603(12) . ?
S2 C9 1.7417(12) . ?
Si1 O3 1.6710(10) . ?
Si1 O2 1.6781(9) . ?
Si1 O1 1.6720(10) . ?
Si1 N1 2.1219(12) . ?
Si1 C15 1.8905(13) . ?
O3 C3 1.4213(13) . ?
O2 C2 1.4189(14) . ?
O1 C1 1.4202(14) . ?
N2 C8 1.3978(14) . ?
N2 C7 1.3010(15) . ?
N1 C6 1.4806(15) . ?
N1 C5 1.4756(14) . ?
N1 C4 1.4789(15) . ?
C11 H11 0.9300 . ?
C11 C10 1.3896(17) . ?
C11 C12 1.3989(18) . ?
C10 H10 0.9300 . ?
C10 C8 1.4005(16) . ?
C8 C9 1.4087(16) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5252(15) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C6 1.5218(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C2 1.5242(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C4 1.5259(17) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C9 C13 1.3933(15) . ?
C13 H13 0.9300 . ?
C13 C12 1.3901(17) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C14 100.87(5) . . ?
C9 S2 C7 88.63(5) . . ?
O3 Si1 O2 120.32(5) . . ?
O3 Si1 O1 118.61(5) . . ?
O3 Si1 N1 83.64(4) . . ?
O3 Si1 C15 94.85(4) . . ?
O2 Si1 N1 83.89(4) . . ?
O2 Si1 C15 98.09(5) . . ?
O1 Si1 O2 117.60(5) . . ?
O1 Si1 N1 83.83(4) . . ?
O1 Si1 C15 95.71(4) . . ?
C15 Si1 N1 177.94(4) . . ?
C3 O3 Si1 122.86(7) . . ?
C2 O2 Si1 122.29(7) . . ?
C1 O1 Si1 122.93(7) . . ?
C7 N2 C8 109.92(9) . . ?
C6 N1 Si1 104.73(7) . . ?
C5 N1 Si1 105.13(7) . . ?
C5 N1 C6 113.39(9) . . ?
C5 N1 C4 113.76(9) . . ?
C4 N1 Si1 105.10(7) . . ?
C4 N1 C6 113.52(9) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.95(11) . . ?
C12 C11 H11 119.5 . . ?
C11 C10 H10 120.6 . . ?
C11 C10 C8 118.78(11) . . ?
C8 C10 H10 120.6 . . ?
N2 C8 C10 125.09(10) . . ?
N2 C8 C9 115.44(10) . . ?
C10 C8 C9 119.46(10) . . ?
S1 C7 S2 117.26(6) . . ?
N2 C7 S1 126.13(8) . . ?
N2 C7 S2 116.60(8) . . ?
S1 C14 H14A 110.1 . . ?
S1 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 S1 108.11(7) . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
Si1 C15 H15A 108.5 . . ?
Si1 C15 H15B 108.5 . . ?
C14 C15 Si1 115.06(7) . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
O3 C3 H3A 110.0 . . ?
O3 C3 H3B 110.0 . . ?
O3 C3 C6 108.38(9) . . ?
H3A C3 H3B 108.4 . . ?
C6 C3 H3A 110.0 . . ?
C6 C3 H3B 110.0 . . ?
N1 C6 C3 105.55(9) . . ?
N1 C6 H6A 110.6 . . ?
N1 C6 H6B 110.6 . . ?
C3 C6 H6A 110.6 . . ?
C3 C6 H6B 110.6 . . ?
H6A C6 H6B 108.8 . . ?
N1 C5 H5A 110.6 . . ?
N1 C5 H5B 110.6 . . ?
N1 C5 C2 105.88(9) . . ?
H5A C5 H5B 108.7 . . ?
C2 C5 H5A 110.6 . . ?
C2 C5 H5B 110.6 . . ?
O2 C2 C5 108.78(9) . . ?
O2 C2 H2A 109.9 . . ?
O2 C2 H2B 109.9 . . ?
C5 C2 H2A 109.9 . . ?
C5 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
O1 C1 C4 109.12(9) . . ?
H1A C1 H1B 108.3 . . ?
C4 C1 H1A 109.9 . . ?
C4 C1 H1B 109.9 . . ?
N1 C4 C1 105.94(9) . . ?
N1 C4 H4A 110.5 . . ?
N1 C4 H4B 110.5 . . ?
C1 C4 H4A 110.5 . . ?
C1 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C8 C9 S2 109.41(8) . . ?
C13 C9 S2 128.67(9) . . ?
C13 C9 C8 121.92(10) . . ?
C9 C13 H13 121.2 . . ?
C12 C13 C9 117.65(11) . . ?
C12 C13 H13 121.2 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.23(11) . . ?
C13 C12 H12 119.4 . . ?

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
S1 C14 C15 Si1 167.23(5) . . . . ?
S2 C9 C13 C12 -179.74(9) . . . . ?
Si1 O3 C3 C6 25.87(12) . . . . ?
Si1 O2 C2 C5 26.81(13) . . . . ?
Si1 O1 C1 C4 22.95(13) . . . . ?
Si1 N1 C6 C3 36.01(9) . . . . ?
Si1 N1 C5 C2 34.37(10) . . . . ?
Si1 N1 C4 C1 34.40(9) . . . . ?
O3 Si1 O2 C2 74.10(10) . . . . ?
O3 Si1 O1 C1 -80.96(9) . . . . ?
O3 Si1 N1 C6 -20.36(7) . . . . ?
O3 Si1 N1 C5 -140.12(7) . . . . ?
O3 Si1 N1 C4 99.54(8) . . . . ?
O3 Si1 C15 C14 162.02(8) . . . . ?
O3 C3 C6 N1 -39.99(11) . . . . ?
O2 Si1 O3 C3 -82.35(9) . . . . ?
O2 Si1 O1 C1 78.11(9) . . . . ?
O2 Si1 N1 C6 101.17(7) . . . . ?
O2 Si1 N1 C5 -18.59(7) . . . . ?
O2 Si1 N1 C4 -138.94(7) . . . . ?
O2 Si1 C15 C14 40.43(8) . . . . ?
O1 Si1 O3 C3 76.13(9) . . . . ?
O1 Si1 O2 C2 -84.59(9) . . . . ?
O1 Si1 N1 C6 -140.13(7) . . . . ?
O1 Si1 N1 C5 100.11(8) . . . . ?
O1 Si1 N1 C4 -20.24(7) . . . . ?
O1 Si1 C15 C14 -78.54(9) . . . . ?
O1 C1 C4 N1 -37.36(12) . . . . ?
N2 C8 C9 S2 0.19(12) . . . . ?
N2 C8 C9 C13 -179.40(10) . . . . ?
N1 Si1 O3 C3 -3.26(8) . . . . ?
N1 Si1 O2 C2 -4.84(9) . . . . ?
N1 Si1 O1 C1 -1.67(9) . . . . ?
N1 Si1 C15 C14 -155.6(12) . . . . ?
N1 C5 C2 O2 -39.42(12) . . . . ?
C11 C10 C8 N2 179.46(10) . . . . ?
C11 C10 C8 C9 0.59(16) . . . . ?
C10 C11 C12 C13 -0.55(18) . . . . ?
C10 C8 C9 S2 179.18(8) . . . . ?
C10 C8 C9 C13 -0.42(16) . . . . ?
C8 N2 C7 S1 -178.17(8) . . . . ?
C8 N2 C7 S2 0.10(12) . . . . ?
C8 C9 C13 C12 -0.23(16) . . . . ?
C7 S1 C14 C15 179.35(7) . . . . ?
C7 S2 C9 C8 -0.11(8) . . . . ?
C7 S2 C9 C13 179.45(11) . . . . ?
C7 N2 C8 C10 -179.11(10) . . . . ?
C7 N2 C8 C9 -0.19(13) . . . . ?
C14 S1 C7 S2 -172.01(6) . . . . ?
C14 S1 C7 N2 6.26(11) . . . . ?
C15 Si1 O3 C3 175.34(8) . . . . ?
C15 Si1 O2 C2 174.58(9) . . . . ?
C15 Si1 O1 C1 -179.66(9) . . . . ?
C15 Si1 N1 C6 -62.8(13) . . . . ?
C15 Si1 N1 C5 177(34) . . . . ?
C15 Si1 N1 C4 57.1(13) . . . . ?
C6 N1 C5 C2 -79.46(11) . . . . ?
C6 N1 C4 C1 148.27(9) . . . . ?
C5 N1 C6 C3 150.08(9) . . . . ?
C5 N1 C4 C1 -80.07(11) . . . . ?
C4 N1 C6 C3 -78.08(11) . . . . ?
C4 N1 C5 C2 148.82(9) . . . . ?
C9 S2 C7 S1 178.44(7) . . . . ?
C9 S2 C7 N2 0.00(9) . . . . ?
C9 C13 C12 C11 0.72(17) . . . . ?
C12 C11 C10 C8 -0.12(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
