#------------------------------------------------------------------------------ #$Date: 2023-12-05 02:34:44 +0200 (Tue, 05 Dec 2023) $ #$Revision: 288025 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247827.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_7247827 loop_ _publ_author_name 'Li, Zengzeng' 'Lu, Fei' 'Xu, Qingchun' 'Liu, Gang' 'Zhao, Ximei' 'Wang, Guanghui' _publ_section_title ; Unexpected stereoselective CuBr2-catalyzed cascade reaction of 2-ethynylanilines with silylynamides: facile and atom-economical access to N-vinylsilylindoles ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC04244H _journal_year 2023 _chemical_formula_sum 'C29 H40 N2 O4 S Si' _chemical_formula_weight 540.78 _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 mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-10-05 deposited with the CCDC. 2023-12-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.697(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.2243(4) _cell_length_b 10.5039(3) _cell_length_c 23.3691(8) _cell_measurement_reflns_used 4564 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 71.1450 _cell_measurement_theta_min 3.7940 _cell_volume 2999.34(17) _computing_cell_refinement 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_unetI/netI 0.0402 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 10887 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.245 _diffrn_reflns_theta_max 67.245 _diffrn_reflns_theta_min 3.617 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 1.618 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78214 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour WHITE _exptl_crystal_density_diffrn 1.198 _exptl_crystal_description BLOCK _exptl_crystal_F_000 1160 _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.603 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 352 _refine_ls_number_reflns 5363 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0615 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1039P)^2^+0.9565P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1674 _refine_ls_wR_factor_ref 0.1835 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4100 _reflns_number_total 5363 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc04244h2.cif _cod_data_source_block exp_13211 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247827 _shelx_shelxl_version_number 2018/3 _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. ; _shelx_estimated_absorpt_t_min 0.817 _shelx_estimated_absorpt_t_max 0.829 _shelx_res_file ; TITL exp_13211_a.res in P2(1)/c exp_13211.res created by SHELXL-2018/3 at 20:24:24 on 05-Oct-2023 CELL 1.54184 12.2243 10.5039 23.3691 90 91.697 90 ZERR 4 0.0004 0.0003 0.0008 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S Si UNIT 116 160 8 16 4 4 OMIT -2 0 4 OMIT 0 0 2 OMIT -14 1 5 OMIT 2 1 4 OMIT -13 5 3 OMIT -3.00 134.50 L.S. 80 ACTA BOND $H FMAP 2 PLAN 10 LIST 6 SIZE 0.12 0.12 0.13 DFIX 1.52 0.01 C14 C16 C14 C16' WGHT 0.103900 0.956500 FVAR 4.71851 0.66454 SI1 6 0.255106 0.006857 0.597537 11.00000 0.06444 0.03948 = 0.05161 -0.00055 -0.00712 0.00141 S1 5 0.072095 0.467989 0.631950 11.00000 0.05287 0.04865 = 0.07636 -0.01521 0.00458 0.00815 N1 3 0.148230 0.390603 0.586043 11.00000 0.04380 0.04805 = 0.05292 0.00176 0.00188 0.00897 N2 3 0.302658 0.319274 0.640790 11.00000 0.04426 0.04373 = 0.03788 0.00030 -0.00030 -0.00006 O1 4 0.136835 0.483374 0.682822 11.00000 0.06865 0.09544 = 0.08785 -0.04832 0.00318 0.00607 O2 4 0.028310 0.575626 0.601723 11.00000 0.07121 0.04450 = 0.13874 0.00289 0.01453 0.01572 O3 4 0.687089 0.683688 0.566207 11.00000 0.07261 0.10963 = 0.06870 -0.00173 0.01355 -0.03193 O4 4 0.705821 0.681412 0.661007 11.00000 0.05649 0.08537 = 0.06967 -0.00916 0.00098 -0.02279 C1 1 -0.036785 0.366385 0.648137 11.00000 0.04821 0.05557 = 0.05080 -0.01118 0.00528 0.01341 C2 1 -0.138813 0.382955 0.622123 11.00000 0.05996 0.05794 = 0.06087 -0.00191 -0.00142 0.01173 AFIX 43 H2 2 -0.150404 0.447119 0.595200 11.00000 -1.20000 AFIX 0 C3 1 -0.223315 0.303056 0.636608 11.00000 0.05432 0.07456 = 0.07729 -0.01317 -0.00419 0.00051 AFIX 43 H3 2 -0.291794 0.314269 0.618925 11.00000 -1.20000 AFIX 0 C4 1 -0.209403 0.207292 0.676411 11.00000 0.07019 0.06152 = 0.07550 -0.00812 0.01272 0.00114 C5 1 -0.106394 0.191235 0.701361 11.00000 0.08100 0.07363 = 0.06782 0.01463 0.02288 0.01915 AFIX 43 H5 2 -0.094563 0.125908 0.727685 11.00000 -1.20000 AFIX 0 C6 1 -0.021238 0.269965 0.687990 11.00000 0.05658 0.08052 = 0.05450 0.00359 0.00702 0.02052 AFIX 43 H6 2 0.047141 0.258526 0.705753 11.00000 -1.20000 AFIX 0 C7 1 -0.304033 0.123748 0.693010 11.00000 0.10128 0.09648 = 0.14243 0.00855 0.02244 -0.02286 AFIX 137 H7A 2 -0.369335 0.174217 0.694668 11.00000 -1.50000 H7B 2 -0.288369 0.086422 0.729845 11.00000 -1.50000 H7C 2 -0.314489 0.057549 0.665057 11.00000 -1.50000 AFIX 0 C8 1 0.102371 0.382571 0.527317 11.00000 0.06284 0.07797 = 0.05642 0.01270 -0.00484 0.02167 AFIX 137 H8A 2 0.154778 0.343528 0.503055 11.00000 -1.50000 H8B 2 0.085620 0.466604 0.513486 11.00000 -1.50000 H8C 2 0.036754 0.332333 0.527045 11.00000 -1.50000 AFIX 0 C9 1 0.209219 0.282868 0.606794 11.00000 0.03904 0.04493 = 0.03923 0.00141 0.00363 0.00208 C10 1 0.183450 0.164336 0.593661 11.00000 0.04226 0.04673 = 0.04532 0.00002 -0.00270 0.00003 AFIX 43 H10 2 0.112267 0.157167 0.578844 11.00000 -1.20000 AFIX 0 C11 1 0.189059 -0.088332 0.655932 11.00000 0.12352 0.05739 = 0.08321 0.01652 -0.00751 -0.01604 AFIX 13 H11 2 0.220861 -0.173978 0.655993 11.00000 -1.20000 AFIX 0 C12 1 0.206769 -0.033217 0.714222 11.00000 0.23717 0.14045 = 0.07143 0.03339 -0.01090 -0.09714 AFIX 137 H12A 2 0.173116 0.049246 0.715731 11.00000 -1.50000 H12B 2 0.283854 -0.025277 0.722509 11.00000 -1.50000 H12C 2 0.174745 -0.088109 0.741983 11.00000 -1.50000 AFIX 0 C13 1 0.062644 -0.101815 0.647301 11.00000 0.09911 0.10107 = 0.14320 0.00868 0.01544 -0.03002 AFIX 137 H13A 2 0.036395 -0.166619 0.672404 11.00000 -1.50000 H13B 2 0.045510 -0.124910 0.608312 11.00000 -1.50000 H13C 2 0.028181 -0.022220 0.655872 11.00000 -1.50000 AFIX 0 C14 1 0.223550 -0.075640 0.527651 11.00000 0.18664 0.06256 = 0.08082 -0.02334 -0.04055 0.00492 PART 1 AFIX 3 H14 2 0.144350 -0.078682 0.532894 21.00000 -1.20000 PART 2 H14' 2 0.289612 -0.051034 0.507623 -21.00000 -1.20000 PART 0 AFIX 0 C15 1 0.237268 -0.213677 0.525724 11.00000 0.20428 0.07388 = 0.10748 -0.03035 -0.02614 0.00777 AFIX 137 H15A 2 0.234930 -0.241679 0.486602 11.00000 -1.50000 H15B 2 0.179389 -0.253768 0.545969 11.00000 -1.50000 H15C 2 0.306503 -0.236321 0.543333 11.00000 -1.50000 PART 1 AFIX 0 C16 1 0.216316 0.001531 0.475636 21.00000 0.18116 0.10274 = 0.06059 -0.01501 -0.01126 -0.00155 AFIX 3 H16A 2 0.288168 0.014235 0.461144 21.00000 -1.50000 H16B 2 0.184394 0.082505 0.484324 21.00000 -1.50000 H16C 2 0.171337 -0.041344 0.447316 21.00000 -1.50000 PART 2 AFIX 0 C16' 1 0.137638 -0.025371 0.487372 -21.00000 0.11905 0.08201 = 0.06355 -0.02129 -0.04984 0.00438 AFIX 3 H16D 2 0.146137 -0.063711 0.450479 -21.00000 -1.50000 H16E 2 0.145713 0.065250 0.484238 -21.00000 -1.50000 H16F 2 0.066282 -0.044859 0.501059 -21.00000 -1.50000 PART 0 AFIX 0 C17 1 0.406261 0.029301 0.609478 11.00000 0.06494 0.06353 = 0.11411 -0.02454 -0.01799 0.01595 AFIX 13 H17 2 0.416163 0.072907 0.646341 11.00000 -1.20000 AFIX 0 C18 1 0.457656 0.113642 0.565155 11.00000 0.07625 0.08476 = 0.16278 -0.03564 0.04687 0.00038 AFIX 137 H18A 2 0.531653 0.133028 0.577009 11.00000 -1.50000 H18B 2 0.416522 0.191187 0.561336 11.00000 -1.50000 H18C 2 0.457391 0.070205 0.529007 11.00000 -1.50000 AFIX 0 C19 1 0.468902 -0.098807 0.614952 11.00000 0.10395 0.09583 = 0.21314 -0.03613 -0.06221 0.05252 AFIX 137 H19A 2 0.460439 -0.145628 0.579819 11.00000 -1.50000 H19B 2 0.439872 -0.147714 0.645710 11.00000 -1.50000 H19C 2 0.545151 -0.082339 0.622713 11.00000 -1.50000 AFIX 0 C20 1 0.324757 0.279934 0.696404 11.00000 0.05990 0.05353 = 0.03949 0.00518 0.00207 -0.00449 AFIX 43 H20 2 0.283812 0.220657 0.716154 11.00000 -1.20000 AFIX 0 C21 1 0.413875 0.339797 0.717668 11.00000 0.06485 0.06701 = 0.03965 0.00601 -0.00825 -0.00372 AFIX 43 H21 2 0.445514 0.328487 0.753994 11.00000 -1.20000 AFIX 0 C22 1 0.451504 0.424070 0.674505 11.00000 0.04977 0.05150 = 0.03910 -0.00368 -0.00247 0.00007 C23 1 0.541163 0.505885 0.670832 11.00000 0.05109 0.05945 = 0.04669 -0.00704 -0.00645 -0.00283 AFIX 43 H23 2 0.588715 0.517704 0.702184 11.00000 -1.20000 AFIX 0 C24 1 0.558170 0.568844 0.620099 11.00000 0.04433 0.04938 = 0.05532 -0.00571 0.00502 0.00262 C25 1 0.484809 0.552185 0.572796 11.00000 0.05618 0.05259 = 0.04367 0.00171 0.00476 -0.00214 AFIX 43 H25 2 0.497550 0.595444 0.538916 11.00000 -1.20000 AFIX 0 C26 1 0.395427 0.473975 0.575554 11.00000 0.04831 0.05163 = 0.03854 0.00151 -0.00260 -0.00085 AFIX 43 H26 2 0.347206 0.464063 0.544340 11.00000 -1.20000 AFIX 0 C27 1 0.379353 0.409705 0.626908 11.00000 0.04354 0.04305 = 0.04233 -0.00402 0.00207 0.00393 C28 1 0.655389 0.650497 0.611976 11.00000 0.05073 0.05629 = 0.06426 -0.00907 0.00528 -0.00048 C29 1 0.805410 0.755285 0.656784 11.00000 0.06488 0.10165 = 0.09803 -0.01569 0.00476 -0.03481 AFIX 137 H29A 2 0.863301 0.701349 0.644131 11.00000 -1.50000 H29B 2 0.825190 0.790220 0.693615 11.00000 -1.50000 H29C 2 0.793696 0.823211 0.629809 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_13211_a.res in P2(1)/c REM wR2 = 0.183464, GooF = S = 1.03576, Restrained GooF = 1.03994 for all data REM R1 = 0.061525 for 4100 Fo > 4sig(Fo) and 0.078632 for all 5363 data REM 352 parameters refined using 2 restraints END WGHT 0.1047 0.9475 REM Highest difference peak 0.603, deepest hole -0.514, 1-sigma level 0.060 Q1 1 0.2826 -0.2143 0.6716 11.00000 0.05 0.60 Q2 1 0.2705 -0.0684 0.6748 11.00000 0.05 0.41 Q3 1 0.4807 0.3305 0.7825 11.00000 0.05 0.40 Q4 1 0.1140 0.4199 0.6062 11.00000 0.05 0.28 Q5 1 0.1295 -0.1565 0.5251 11.00000 0.05 0.28 Q6 1 0.1034 -0.1332 0.5281 11.00000 0.05 0.27 Q7 1 0.2200 0.0947 0.6001 11.00000 0.05 0.26 Q8 1 0.4032 0.3996 0.5997 11.00000 0.05 0.21 Q9 1 0.1186 -0.0589 0.6890 11.00000 0.05 0.20 Q10 1 0.0961 0.4483 0.6638 11.00000 0.05 0.19 ; _shelx_res_checksum 18018 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' '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_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 Si1 Si 0.25511(7) 0.00686(7) 0.59754(3) 0.0520(2) Uani 1 1 d . . . . . S1 S 0.07210(6) 0.46799(7) 0.63195(4) 0.0592(2) Uani 1 1 d . . . . . N1 N 0.14823(18) 0.3906(2) 0.58604(10) 0.0482(5) Uani 1 1 d . . . . . N2 N 0.30266(17) 0.3193(2) 0.64079(8) 0.0420(5) Uani 1 1 d . . . . . O1 O 0.1368(2) 0.4834(3) 0.68282(11) 0.0840(8) Uani 1 1 d . . . . . O2 O 0.0283(2) 0.5756(2) 0.60172(13) 0.0846(8) Uani 1 1 d . . . . . O3 O 0.6871(2) 0.6837(3) 0.56621(11) 0.0834(8) Uani 1 1 d . . . . . O4 O 0.70582(18) 0.6814(2) 0.66101(10) 0.0705(6) Uani 1 1 d . . . . . C1 C -0.0368(2) 0.3664(3) 0.64814(12) 0.0515(7) Uani 1 1 d . . . . . C2 C -0.1388(3) 0.3830(3) 0.62212(14) 0.0597(8) Uani 1 1 d . . . . . H2 H -0.150404 0.447119 0.595200 0.072 Uiso 1 1 calc R U . . . C3 C -0.2233(3) 0.3031(4) 0.63661(15) 0.0688(9) Uani 1 1 d . . . . . H3 H -0.291794 0.314269 0.618925 0.083 Uiso 1 1 calc R U . . . C4 C -0.2094(3) 0.2073(3) 0.67641(16) 0.0689(9) Uani 1 1 d . . . . . C5 C -0.1064(3) 0.1912(4) 0.70136(15) 0.0737(10) Uani 1 1 d . . . . . H5 H -0.094563 0.125908 0.727685 0.088 Uiso 1 1 calc R U . . . C6 C -0.0212(3) 0.2700(3) 0.68799(13) 0.0638(8) Uani 1 1 d . . . . . H6 H 0.047141 0.258526 0.705753 0.077 Uiso 1 1 calc R U . . . C7 C -0.3040(4) 0.1237(5) 0.6930(2) 0.1130(16) Uani 1 1 d . . . . . H7A H -0.369335 0.174217 0.694668 0.170 Uiso 1 1 calc R U . . . H7B H -0.288369 0.086422 0.729845 0.170 Uiso 1 1 calc R U . . . H7C H -0.314489 0.057549 0.665057 0.170 Uiso 1 1 calc R U . . . C8 C 0.1024(3) 0.3826(4) 0.52732(13) 0.0659(9) Uani 1 1 d . . . . . H8A H 0.154778 0.343528 0.503055 0.099 Uiso 1 1 calc R U . . . H8B H 0.085620 0.466604 0.513486 0.099 Uiso 1 1 calc R U . . . H8C H 0.036754 0.332333 0.527045 0.099 Uiso 1 1 calc R U . . . C9 C 0.2092(2) 0.2829(2) 0.60679(10) 0.0410(6) Uani 1 1 d . . . . . C10 C 0.1835(2) 0.1643(3) 0.59366(11) 0.0448(6) Uani 1 1 d . . . . . H10 H 0.112267 0.157167 0.578844 0.054 Uiso 1 1 calc R U . . . C11 C 0.1891(4) -0.0883(4) 0.65593(17) 0.0882(12) Uani 1 1 d . . . . . H11 H 0.220861 -0.173978 0.655993 0.106 Uiso 1 1 calc R U . . . C12 C 0.2068(6) -0.0332(6) 0.71422(19) 0.150(3) Uani 1 1 d . . . . . H12A H 0.173116 0.049246 0.715731 0.225 Uiso 1 1 calc R U . . . H12B H 0.283854 -0.025277 0.722509 0.225 Uiso 1 1 calc R U . . . H12C H 0.174745 -0.088109 0.741983 0.225 Uiso 1 1 calc R U . . . C13 C 0.0626(4) -0.1018(5) 0.6473(2) 0.1142(17) Uani 1 1 d . . . . . H13A H 0.036395 -0.166619 0.672404 0.171 Uiso 1 1 calc R U . . . H13B H 0.045510 -0.124910 0.608312 0.171 Uiso 1 1 calc R U . . . H13C H 0.028181 -0.022220 0.655872 0.171 Uiso 1 1 calc R U . . . C14 C 0.2236(5) -0.0756(4) 0.52765(18) 0.1109(18) Uani 1 1 d D . . . . H14 H 0.144350 -0.078682 0.532894 0.133 Uiso 0.66(3) 1 d R U P A 1 H14' H 0.289612 -0.051034 0.507623 0.133 Uiso 0.34(3) 1 d R U P A 2 C15 C 0.2373(6) -0.2137(5) 0.5257(2) 0.129(2) Uani 1 1 d . . . . . H15A H 0.234930 -0.241679 0.486602 0.194 Uiso 1 1 calc R U . . . H15B H 0.179389 -0.253768 0.545969 0.194 Uiso 1 1 calc R U . . . H15C H 0.306503 -0.236321 0.543333 0.194 Uiso 1 1 calc R U . . . C16 C 0.216(2) 0.0015(9) 0.4756(3) 0.115(5) Uani 0.66(3) 1 d D . P A 1 H16A H 0.288168 0.014235 0.461144 0.173 Uiso 0.66(3) 1 d R U P A 1 H16B H 0.184394 0.082505 0.484324 0.173 Uiso 0.66(3) 1 d R U P A 1 H16C H 0.171337 -0.041344 0.447316 0.173 Uiso 0.66(3) 1 d R U P A 1 C16' C 0.138(2) -0.0254(17) 0.4874(9) 0.089(8) Uani 0.34(3) 1 d D . P A 2 H16D H 0.146137 -0.063711 0.450479 0.134 Uiso 0.34(3) 1 d R U P A 2 H16E H 0.145713 0.065250 0.484238 0.134 Uiso 0.34(3) 1 d R U P A 2 H16F H 0.066282 -0.044859 0.501059 0.134 Uiso 0.34(3) 1 d R U P A 2 C17 C 0.4063(3) 0.0293(4) 0.6095(2) 0.0813(11) Uani 1 1 d . . . . . H17 H 0.416163 0.072907 0.646341 0.098 Uiso 1 1 calc R U . . . C18 C 0.4577(4) 0.1136(4) 0.5652(2) 0.1071(17) Uani 1 1 d . . . . . H18A H 0.531653 0.133028 0.577009 0.161 Uiso 1 1 calc R U . . . H18B H 0.416522 0.191187 0.561336 0.161 Uiso 1 1 calc R U . . . H18C H 0.457391 0.070205 0.529007 0.161 Uiso 1 1 calc R U . . . C19 C 0.4689(4) -0.0988(5) 0.6150(3) 0.139(2) Uani 1 1 d . . . . . H19A H 0.460439 -0.145628 0.579819 0.208 Uiso 1 1 calc R U . . . H19B H 0.439872 -0.147714 0.645710 0.208 Uiso 1 1 calc R U . . . H19C H 0.545151 -0.082339 0.622713 0.208 Uiso 1 1 calc R U . . . C20 C 0.3248(2) 0.2799(3) 0.69640(11) 0.0510(7) Uani 1 1 d . . . . . H20 H 0.283812 0.220657 0.716154 0.061 Uiso 1 1 calc R U . . . C21 C 0.4139(3) 0.3398(3) 0.71767(12) 0.0574(7) Uani 1 1 d . . . . . H21 H 0.445514 0.328487 0.753994 0.069 Uiso 1 1 calc R U . . . C22 C 0.4515(2) 0.4241(3) 0.67451(11) 0.0469(6) Uani 1 1 d . . . . . C23 C 0.5412(2) 0.5059(3) 0.67083(12) 0.0526(7) Uani 1 1 d . . . . . H23 H 0.588715 0.517704 0.702184 0.063 Uiso 1 1 calc R U . . . C24 C 0.5582(2) 0.5688(3) 0.62010(12) 0.0496(6) Uani 1 1 d . . . . . C25 C 0.4848(2) 0.5522(3) 0.57280(11) 0.0507(6) Uani 1 1 d . . . . . H25 H 0.497550 0.595444 0.538916 0.061 Uiso 1 1 calc R U . . . C26 C 0.3954(2) 0.4740(3) 0.57555(11) 0.0462(6) Uani 1 1 d . . . . . H26 H 0.347206 0.464063 0.544340 0.055 Uiso 1 1 calc R U . . . C27 C 0.3794(2) 0.4097(2) 0.62691(10) 0.0430(6) Uani 1 1 d . . . . . C28 C 0.6554(2) 0.6505(3) 0.61198(14) 0.0570(7) Uani 1 1 d . . . . . C29 C 0.8054(3) 0.7553(4) 0.65678(18) 0.0881(12) Uani 1 1 d . . . . . H29A H 0.863301 0.701349 0.644131 0.132 Uiso 1 1 calc R U . . . H29B H 0.825190 0.790220 0.693615 0.132 Uiso 1 1 calc R U . . . H29C H 0.793696 0.823211 0.629809 0.132 Uiso 1 1 calc R U . . . 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 Si1 0.0644(5) 0.0395(4) 0.0516(4) -0.0006(3) -0.0071(4) 0.0014(3) S1 0.0529(4) 0.0487(4) 0.0764(5) -0.0152(4) 0.0046(3) 0.0081(3) N1 0.0438(12) 0.0481(13) 0.0529(12) 0.0018(10) 0.0019(10) 0.0090(10) N2 0.0443(12) 0.0437(12) 0.0379(10) 0.0003(9) -0.0003(8) -0.0001(9) O1 0.0687(15) 0.0954(19) 0.0878(17) -0.0483(15) 0.0032(13) 0.0061(13) O2 0.0712(15) 0.0445(13) 0.139(2) 0.0029(14) 0.0145(15) 0.0157(11) O3 0.0726(15) 0.110(2) 0.0687(14) -0.0017(14) 0.0135(12) -0.0319(15) O4 0.0565(13) 0.0854(17) 0.0697(14) -0.0092(12) 0.0010(10) -0.0228(12) C1 0.0482(15) 0.0556(17) 0.0508(15) -0.0112(13) 0.0053(12) 0.0134(13) C2 0.0600(18) 0.0579(18) 0.0609(17) -0.0019(14) -0.0014(14) 0.0117(15) C3 0.0543(19) 0.075(2) 0.077(2) -0.0132(18) -0.0042(16) 0.0005(16) C4 0.070(2) 0.062(2) 0.076(2) -0.0081(17) 0.0127(17) 0.0011(17) C5 0.081(2) 0.074(2) 0.068(2) 0.0146(17) 0.0229(18) 0.0192(19) C6 0.0566(18) 0.081(2) 0.0545(16) 0.0036(16) 0.0070(14) 0.0205(16) C7 0.101(3) 0.096(3) 0.142(4) 0.009(3) 0.022(3) -0.023(3) C8 0.0628(19) 0.078(2) 0.0564(17) 0.0127(16) -0.0048(14) 0.0217(16) C9 0.0390(13) 0.0449(14) 0.0392(12) 0.0014(10) 0.0036(10) 0.0021(11) C10 0.0423(14) 0.0467(15) 0.0453(13) 0.0000(11) -0.0027(10) 0.0000(11) C11 0.124(3) 0.057(2) 0.083(2) 0.0165(19) -0.008(2) -0.016(2) C12 0.237(7) 0.140(5) 0.071(3) 0.033(3) -0.011(4) -0.097(5) C13 0.099(3) 0.101(4) 0.143(4) 0.009(3) 0.015(3) -0.030(3) C14 0.187(5) 0.063(2) 0.081(3) -0.023(2) -0.041(3) 0.005(3) C15 0.204(6) 0.074(3) 0.107(4) -0.030(3) -0.026(4) 0.008(3) C16 0.181(16) 0.103(6) 0.061(4) -0.015(4) -0.011(5) -0.002(7) C16' 0.119(15) 0.082(10) 0.064(9) -0.021(7) -0.050(10) 0.004(9) C17 0.065(2) 0.064(2) 0.114(3) -0.025(2) -0.018(2) 0.0159(17) C18 0.076(3) 0.085(3) 0.163(5) -0.036(3) 0.047(3) 0.000(2) C19 0.104(4) 0.096(4) 0.213(6) -0.036(4) -0.062(4) 0.053(3) C20 0.0599(17) 0.0535(16) 0.0395(13) 0.0052(12) 0.0021(12) -0.0045(13) C21 0.0649(18) 0.0670(19) 0.0396(13) 0.0060(13) -0.0083(12) -0.0037(15) C22 0.0498(15) 0.0515(16) 0.0391(12) -0.0037(11) -0.0025(11) 0.0001(12) C23 0.0511(16) 0.0594(17) 0.0467(14) -0.0070(12) -0.0064(12) -0.0028(13) C24 0.0443(15) 0.0494(16) 0.0553(15) -0.0057(12) 0.0050(12) 0.0026(12) C25 0.0562(16) 0.0526(16) 0.0437(13) 0.0017(12) 0.0048(12) -0.0021(13) C26 0.0483(15) 0.0516(16) 0.0385(12) 0.0015(11) -0.0026(11) -0.0009(12) C27 0.0435(14) 0.0431(14) 0.0423(13) -0.0040(11) 0.0021(10) 0.0039(11) C28 0.0507(16) 0.0563(18) 0.0643(18) -0.0091(14) 0.0053(14) -0.0005(14) C29 0.065(2) 0.102(3) 0.098(3) -0.016(2) 0.005(2) -0.035(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.2541 0.3302 '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 C10 Si1 C17 110.70(14) . . ? C10 Si1 C14 106.36(16) . . ? C17 Si1 C14 111.3(2) . . ? C10 Si1 C11 107.02(17) . . ? C17 Si1 C11 113.5(2) . . ? C14 Si1 C11 107.6(2) . . ? O1 S1 O2 121.06(17) . . ? O1 S1 N1 106.80(13) . . ? O2 S1 N1 106.14(15) . . ? O1 S1 C1 107.25(16) . . ? O2 S1 C1 108.19(15) . . ? N1 S1 C1 106.60(13) . . ? C9 N1 C8 116.8(2) . . ? C9 N1 S1 117.77(17) . . ? C8 N1 S1 115.31(18) . . ? C27 N2 C20 108.1(2) . . ? C27 N2 C9 126.4(2) . . ? C20 N2 C9 125.1(2) . . ? C28 O4 C29 116.3(3) . . ? C2 C1 C6 119.5(3) . . ? C2 C1 S1 120.6(2) . . ? C6 C1 S1 120.0(2) . . ? C3 C2 C1 119.2(3) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C4 C3 C2 122.1(3) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 117.8(3) . . ? C3 C4 C7 121.1(4) . . ? C5 C4 C7 121.0(4) . . ? C6 C5 C4 121.2(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N2 124.4(2) . . ? C10 C9 N1 123.3(2) . . ? N2 C9 N1 112.2(2) . . ? C9 C10 Si1 135.6(2) . . ? C9 C10 H10 112.2 . . ? Si1 C10 H10 112.2 . . ? C12 C11 C13 105.7(4) . . ? C12 C11 Si1 113.6(3) . . ? C13 C11 Si1 113.4(3) . . ? C12 C11 H11 108.0 . . ? C13 C11 H11 108.0 . . ? Si1 C11 H11 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C16 C14 C15 121.9(5) . . ? C15 C14 C16' 114.4(8) . . ? C16 C14 Si1 118.2(5) . . ? C15 C14 Si1 117.6(3) . . ? C16' C14 Si1 120.6(7) . . ? C16 C14 H14 95.0 . . ? C15 C14 H14 94.9 . . ? Si1 C14 H14 94.8 . . ? C15 C14 H14' 98.6 . . ? C16' C14 H14' 100.4 . . ? Si1 C14 H14' 98.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.7 . . ? C14 C16 H16B 109.3 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.4 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C16' H16D 109.1 . . ? C14 C16' H16E 109.2 . . ? H16D C16' H16E 109.5 . . ? C14 C16' H16F 110.2 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? C18 C17 C19 110.5(4) . . ? C18 C17 Si1 113.5(3) . . ? C19 C17 Si1 112.6(3) . . ? C18 C17 H17 106.6 . . ? C19 C17 H17 106.6 . . ? Si1 C17 H17 106.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 N2 110.0(2) . . ? C21 C20 H20 125.0 . . ? N2 C20 H20 125.0 . . ? C20 C21 C22 107.7(2) . . ? C20 C21 H21 126.1 . . ? C22 C21 H21 126.1 . . ? C23 C22 C27 119.5(2) . . ? C23 C22 C21 134.0(3) . . ? C27 C22 C21 106.5(2) . . ? C24 C23 C22 119.1(3) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 C28 122.0(3) . . ? C25 C24 C28 117.6(3) . . ? C26 C25 C24 121.7(3) . . ? C26 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C25 C26 C27 117.6(2) . . ? C25 C26 H26 121.2 . . ? C27 C26 H26 121.2 . . ? N2 C27 C26 130.5(2) . . ? N2 C27 C22 107.6(2) . . ? C26 C27 C22 121.8(2) . . ? O3 C28 O4 123.0(3) . . ? O3 C28 C24 124.3(3) . . ? O4 C28 C24 112.7(3) . . ? O4 C29 H29A 109.5 . . ? O4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? 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 Si1 C10 1.873(3) . ? Si1 C17 1.875(4) . ? Si1 C14 1.879(4) . ? Si1 C11 1.892(4) . ? S1 O1 1.418(3) . ? S1 O2 1.429(3) . ? S1 N1 1.654(2) . ? S1 C1 1.756(3) . ? N1 C9 1.432(3) . ? N1 C8 1.469(4) . ? N2 C27 1.380(3) . ? N2 C20 1.383(3) . ? N2 C9 1.424(3) . ? O3 C28 1.200(4) . ? O4 C28 1.325(4) . ? O4 C29 1.449(4) . ? C1 C2 1.382(4) . ? C1 C6 1.385(4) . ? C2 C3 1.381(5) . ? C2 H2 0.9300 . ? C3 C4 1.377(5) . ? C3 H3 0.9300 . ? C4 C5 1.382(5) . ? C4 C7 1.512(5) . ? C5 C6 1.373(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.318(4) . ? C10 H10 0.9300 . ? C11 C12 1.490(6) . ? C11 C13 1.559(6) . ? C11 H11 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C16 1.462(7) . ? C14 C15 1.460(6) . ? C14 C16' 1.486(8) . ? C14 H14 0.9800 . ? C14 H14' 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C16' H16D 0.9600 . ? C16' H16E 0.9600 . ? C16' H16F 0.9600 . ? C17 C18 1.514(6) . ? C17 C19 1.552(5) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.341(4) . ? C20 H20 0.9300 . ? C21 C22 1.428(4) . ? C21 H21 0.9300 . ? C22 C23 1.397(4) . ? C22 C27 1.407(4) . ? C23 C24 1.379(4) . ? C23 H23 0.9300 . ? C24 C25 1.414(4) . ? C24 C28 1.482(4) . ? C25 C26 1.370(4) . ? C25 H25 0.9300 . ? C26 C27 1.396(4) . ? C26 H26 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ?