#------------------------------------------------------------------------------ #$Date: 2021-04-22 06:24:19 +0300 (Thu, 22 Apr 2021) $ #$Revision: 264383 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060606.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7060606 loop_ _publ_author_name 'Trofimova, Olga' 'Grebneva, Ekaterina' 'Bolgova, Yuliya' 'Belogolova, Elena Fedorovna' 'Emel’yanov, Artem' 'Albanov, Alexander' 'Borodina, Tatiana' 'Ivanova, Anastasiya' 'Korzhova, Svetlana' 'Pozdnyakov, Alexandr Sergeevich' _publ_section_title ; The synthesis, characterization, and theoretical analysis of novel Si-substituted silylethyl derivatives of 2-mercaptobenzoxazole and 2-mercaptobenzothiazole ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ00793A _journal_year 2021 _chemical_formula_moiety 'C15 H20 N2 O3 S2 Si' _chemical_formula_sum 'C15 H20 N2 O3 S2 Si' _chemical_formula_weight 368.54 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2021-04-15 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-04-16 deposited with the CCDC. 2021-04-21 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 117.361(16) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.187(5) _cell_length_b 10.587(4) _cell_length_c 13.213(5) _cell_measurement_reflns_used 9731 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30.05 _cell_measurement_theta_min 3.09 _cell_volume 1638.3(11) _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)' _diffrn_ambient_temperature 293.15 _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 '\f and \w scans' _diffrn_radiation_monochromator 'Bruker APEX2' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _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_source 'fine-focus sealed tube' _diffrn_standards_number 0 _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 \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.494 _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 _refine_diff_density_max 0.429 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.050 _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_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0239 _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/[\s^2^(Fo^2^)+(0.0288P)^2^+1.0236P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.0638 _reflns_number_gt 3715 _reflns_number_total 3929 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL a_a.res in P2(1)/c CELL 0.71073 13.1872 10.587 13.2134 90 117.361 90 ZERR 4 0.0051 0.004 0.0045 0 0.016 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S Si UNIT 60 80 8 12 8 4 L.S. 10 0 0 PLAN -4 SIZE 0.239 0.337 0.428 TEMP 20 BOND $H HTAB CONF fmap 2 acta OMIT -3 56 REM REM REM WGHT 0.028800 1.023600 FVAR 0.96227 S1 5 0.714588 0.275955 0.582719 11.00000 0.01763 0.00868 = 0.01816 -0.00049 0.01175 0.00047 S2 5 0.813089 0.099893 0.474469 11.00000 0.01508 0.00822 = 0.01948 -0.00082 0.01038 0.00046 SI1 6 0.637717 0.656318 0.679746 11.00000 0.01029 0.00797 = 0.00935 0.00000 0.00529 0.00048 O3 4 0.519963 0.651247 0.697031 11.00000 0.01486 0.00951 = 0.02103 -0.00116 0.01220 0.00043 O2 4 0.632911 0.717164 0.560347 11.00000 0.02350 0.00899 = 0.01367 0.00057 0.01130 -0.00028 O1 4 0.764892 0.649794 0.795333 11.00000 0.01355 0.01304 = 0.01474 -0.00226 0.00173 0.00136 N2 3 0.843168 0.344482 0.479754 11.00000 0.01515 0.01078 = 0.01505 -0.00015 0.00740 0.00082 N1 3 0.641612 0.848514 0.726940 11.00000 0.01454 0.00969 = 0.01309 -0.00131 0.00795 -0.00092 C11 1 1.011628 0.296490 0.321550 11.00000 0.01766 0.02369 = 0.01730 0.00281 0.00988 -0.00149 AFIX 43 H11 2 1.052320 0.341228 0.291552 11.00000 -1.20000 AFIX 0 C10 1 0.959828 0.361224 0.376918 11.00000 0.01736 0.01436 = 0.01696 0.00251 0.00744 -0.00065 AFIX 43 H10 2 0.965643 0.448634 0.384301 11.00000 -1.20000 AFIX 0 C8 1 0.898703 0.292411 0.421399 11.00000 0.01161 0.01259 = 0.01158 0.00071 0.00364 0.00150 C7 1 0.795814 0.255353 0.511259 11.00000 0.01243 0.00988 = 0.01249 -0.00116 0.00489 0.00166 C14 1 0.704182 0.447580 0.582398 11.00000 0.01767 0.00771 = 0.01710 -0.00046 0.01073 0.00051 AFIX 23 H14A 2 0.779750 0.484522 0.622209 11.00000 -1.20000 H14B 2 0.668291 0.478932 0.504730 11.00000 -1.20000 AFIX 0 C15 1 0.632854 0.483466 0.641872 11.00000 0.01308 0.00968 = 0.01274 0.00025 0.00732 0.00030 AFIX 23 H15A 2 0.658935 0.434102 0.711196 11.00000 -1.20000 H15B 2 0.554064 0.460291 0.592802 11.00000 -1.20000 AFIX 0 C3 1 0.480400 0.756356 0.735872 11.00000 0.01398 0.01298 = 0.01839 -0.00077 0.01001 0.00222 AFIX 23 H3A 2 0.508824 0.751373 0.817746 11.00000 -1.20000 H3B 2 0.397615 0.756444 0.700076 11.00000 -1.20000 AFIX 0 C6 1 0.523320 0.876577 0.705175 11.00000 0.01717 0.01176 = 0.02033 -0.00013 0.01100 0.00342 AFIX 23 H6A 2 0.476096 0.898076 0.625719 11.00000 -1.20000 H6B 2 0.522265 0.946560 0.752064 11.00000 -1.20000 AFIX 0 C5 1 0.676910 0.919093 0.652057 11.00000 0.02265 0.01029 = 0.01987 0.00087 0.01318 -0.00227 AFIX 23 H5A 2 0.759477 0.920931 0.684372 11.00000 -1.20000 H5B 2 0.648922 1.005257 0.641952 11.00000 -1.20000 AFIX 0 C2 1 0.624673 0.848982 0.538614 11.00000 0.02622 0.01104 = 0.01687 0.00282 0.01276 0.00020 AFIX 23 H2A 2 0.545243 0.872985 0.494276 11.00000 -1.20000 H2B 2 0.665012 0.870732 0.495416 11.00000 -1.20000 AFIX 0 C1 1 0.817347 0.756637 0.864802 11.00000 0.01480 0.01847 = 0.01439 -0.00370 0.00348 -0.00357 AFIX 23 H1A 2 0.872264 0.793421 0.843611 11.00000 -1.20000 H1B 2 0.857513 0.731265 0.944121 11.00000 -1.20000 AFIX 0 C4 1 0.725644 0.853665 0.848922 11.00000 0.01898 0.01519 = 0.01399 -0.00556 0.00776 -0.00454 AFIX 23 H4A 2 0.689565 0.832829 0.896308 11.00000 -1.20000 H4B 2 0.758647 0.937453 0.869190 11.00000 -1.20000 AFIX 0 C9 1 0.892118 0.159970 0.409972 11.00000 0.00972 0.01285 = 0.01261 0.00014 0.00415 0.00050 C13 1 0.944221 0.094703 0.354802 11.00000 0.01403 0.01535 = 0.01727 -0.00248 0.00677 0.00147 AFIX 43 H13 2 0.939538 0.007205 0.348003 11.00000 -1.20000 AFIX 0 C12 1 1.003453 0.165002 0.310280 11.00000 0.01548 0.02440 = 0.01704 -0.00232 0.00924 0.00163 AFIX 43 H12 2 1.038295 0.123847 0.272293 11.00000 -1.20000 HKLF 4 REM a_a.res in P2(1)/c REM R1 = 0.0239 for 3715 Fo > 4sig(Fo) and 0.0253 for all 3929 data REM 208 parameters refined using 0 restraints END WGHT 0.0288 1.0236 REM Highest difference peak 0.429, deepest hole -0.280, 1-sigma level 0.050 Q1 1 0.6312 0.5589 0.6478 11.00000 0.05 0.43 Q2 1 0.9035 0.2256 0.4191 11.00000 0.05 0.36 Q3 1 0.5036 0.8165 0.7191 11.00000 0.05 0.33 Q4 1 0.6510 0.8854 0.5991 11.00000 0.05 0.30 REM The information below was added by Olex2. REM REM R1 = 0.0239 for 3715 Fo > 4sig(Fo) and 0.0253 for all 54377 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.43, deepest hole -0.28 REM Mean Shift 0, Max Shift 0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0253 REM R1_gt = 0.0239 REM wR_ref = 0.0638 REM GOOF = 1.039 REM Shift_max = 0.001 REM Shift_mean = 0 REM Reflections_all = 54377 REM Reflections_gt = 3715 REM Parameters = n/a REM Hole = -0.28 REM Peak = 0.43 REM Flack = n/a ; _cod_data_source_file d1nj00793a2.cif _cod_data_source_block 2c _cod_original_cell_volume 1638.4(10) _cod_database_code 7060606 _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) ; _olex2_submission_special_instructions 'No special instructions were received' 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' 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 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01763(13) 0.00868(13) 0.01816(14) -0.00049(9) 0.01175(11) 0.00047(9) S2 0.01508(13) 0.00822(13) 0.01948(14) -0.00082(9) 0.01038(11) 0.00046(9) Si1 0.01029(13) 0.00797(13) 0.00935(13) 0.00000(9) 0.00529(11) 0.00048(9) O3 0.0149(4) 0.0095(3) 0.0210(4) -0.0012(3) 0.0122(3) 0.0004(3) O2 0.0235(4) 0.0090(4) 0.0137(4) 0.0006(3) 0.0113(3) -0.0003(3) O1 0.0135(4) 0.0130(4) 0.0147(4) -0.0023(3) 0.0017(3) 0.0014(3) N2 0.0151(4) 0.0108(4) 0.0151(4) -0.0002(3) 0.0074(4) 0.0008(3) N1 0.0145(4) 0.0097(4) 0.0131(4) -0.0013(3) 0.0080(4) -0.0009(3) C11 0.0177(5) 0.0237(6) 0.0173(5) 0.0028(4) 0.0099(4) -0.0015(4) C10 0.0174(5) 0.0144(5) 0.0170(5) 0.0025(4) 0.0074(4) -0.0007(4) C8 0.0116(5) 0.0126(5) 0.0116(5) 0.0007(4) 0.0036(4) 0.0015(4) C7 0.0124(5) 0.0099(5) 0.0125(5) -0.0012(4) 0.0049(4) 0.0017(4) C14 0.0177(5) 0.0077(5) 0.0171(5) -0.0005(4) 0.0107(4) 0.0005(4) C15 0.0131(5) 0.0097(5) 0.0127(5) 0.0002(4) 0.0073(4) 0.0003(4) C3 0.0140(5) 0.0130(5) 0.0184(5) -0.0008(4) 0.0100(4) 0.0022(4) C6 0.0172(5) 0.0118(5) 0.0203(5) -0.0001(4) 0.0110(4) 0.0034(4) C5 0.0226(6) 0.0103(5) 0.0199(5) 0.0009(4) 0.0132(5) -0.0023(4) C2 0.0262(6) 0.0110(5) 0.0169(5) 0.0028(4) 0.0128(5) 0.0002(4) C1 0.0148(5) 0.0185(5) 0.0144(5) -0.0037(4) 0.0035(4) -0.0036(4) C4 0.0190(5) 0.0152(5) 0.0140(5) -0.0056(4) 0.0078(4) -0.0045(4) C9 0.0097(4) 0.0128(5) 0.0126(5) 0.0001(4) 0.0042(4) 0.0005(4) C13 0.0140(5) 0.0154(5) 0.0173(5) -0.0025(4) 0.0068(4) 0.0015(4) C12 0.0155(5) 0.0244(6) 0.0170(5) -0.0023(4) 0.0092(4) 0.0016(4) 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' 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_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_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) . . . . ?