#------------------------------------------------------------------------------ #$Date: 2017-06-07 08:23:19 +0300 (Wed, 07 Jun 2017) $ #$Revision: 197597 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/84/7228406.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_7228406 loop_ _publ_author_name 'Liu, Honglei' 'Zhao, Yan' 'Li, Zhen' 'Jia, Hao' 'Zhang, Cheng' 'Xiao, Yumei' 'Guo, Hongchao' _publ_section_title ; Lewis base-catalyzed diastereoselective [3 + 2] cycloaddition reaction of nitrones with electron-deficient alkenes: an access to isoxazolidine derivatives ; _journal_issue 47 _journal_name_full 'RSC Adv.' _journal_page_first 29515 _journal_paper_doi 10.1039/C7RA04264G _journal_volume 7 _journal_year 2017 _chemical_formula_moiety 'C23 H24 N O5 S2' _chemical_formula_sum 'C23 H24 N O5 S2' _chemical_formula_weight 458.55 _chemical_name_systematic ; ? ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2014-05-22 _audit_creation_method ; Olex2 1.2 (compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816) ; _audit_update_record ; 2017-02-10 deposited with the CCDC. 2017-05-31 downloaded from the CCDC. ; _cell_angle_alpha 104.70(3) _cell_angle_beta 103.61(3) _cell_angle_gamma 102.46(3) _cell_formula_units_Z 2 _cell_length_a 10.184(2) _cell_length_b 10.710(2) _cell_length_c 11.083(2) _cell_measurement_reflns_used 4213 _cell_measurement_temperature 173.1500 _cell_measurement_theta_max 27.4825 _cell_measurement_theta_min 2.0562 _cell_volume 1086.5(5) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2013)' _computing_publication_material 'Olex2 (Dolomanov et al., 2013)' _computing_structure_refinement 'ShelXL (Sheldrick, 2013)' _computing_structure_solution ; 'XS (Sheldrick, 2013)' ; _diffrn_ambient_temperature 173.1500 _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device ; Saturn724 (2x2 bin mode) ; _diffrn_measurement_device_details ; AFC10: Fixed Chi 2 circle ; _diffrn_measurement_device_type 'Saturn724+ CCD' _diffrn_measurement_method dtprofit.ref _diffrn_orient_matrix_type d*Trek _diffrn_orient_matrix_UB_11 -0.0300 _diffrn_orient_matrix_UB_12 -0.0490 _diffrn_orient_matrix_UB_13 -0.0887 _diffrn_orient_matrix_UB_21 0.0442 _diffrn_orient_matrix_UB_22 -0.0908 _diffrn_orient_matrix_UB_23 -0.0001 _diffrn_orient_matrix_UB_31 -0.0668 _diffrn_orient_matrix_UB_32 -0.0675 _diffrn_orient_matrix_UB_33 0.0241 _diffrn_radiation_detector CCD _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_unetI/netI 0.0216 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 14612 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_min 3.189 _diffrn_source 'Sealed Tube' _diffrn_source_current 30.0000 _diffrn_source_power 1.5000 _diffrn_source_voltage 50.0000 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8925 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.401 _exptl_crystal_description block _exptl_crystal_F_000 482 _exptl_crystal_size_max 0.504 _exptl_crystal_size_mid 0.428 _exptl_crystal_size_min 0.31 _refine_diff_density_max 0.348 _refine_diff_density_min -0.794 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 4958 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0373 _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^)+(0.0391P)^2^+0.5926P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.0928 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4756 _reflns_number_total 4958 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra04264g2.cif _cod_data_source_block sa3397 _cod_original_cell_volume 1086.6(4) _cod_database_code 7228406 _shelxl_version_number 2013-4 _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. ; _diffrn_number_total 4964 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: N1(H1), C7(H7), C8(H8), C9(H9) 2.b Aromatic/amide H refined with riding coordinates: C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21) 2.c Idealised Me refined as rotating group: C10(H10A,H10B,H10C), C23(H23A,H23B,H23C) ; _shelx_res_file ; TITL sa3397 in P-1 CELL 0.71073 10.1845 10.71 11.0834 104.703 103.608 102.463 ZERR 2 0.002 0.0021 0.0022 0.03 0.03 0.03 LATT 1 SFAC C H N O S UNIT 46 48 2 10 4 L.S. 4 PLAN 20 BOND fmap 2 MORE -1 ACTA 52 CONF OMIT -1 1 0 OMIT 5 -5 1 OMIT 0 0 1 OMIT 1 0 0 OMIT 0 1 0 OMIT 0 -1 1 REM C:/Users/DELL/Desktop/sa3397/sa3397.hkl WGHT 0.039100 0.592600 FVAR 11.33293 S1 5 0.347380 0.393399 0.781930 11.00000 0.02391 0.01519 = 0.01869 0.00334 0.00770 0.00571 S2 5 0.196172 0.091448 0.926659 11.00000 0.02268 0.01898 = 0.01834 0.00573 0.00844 0.00574 O1 4 0.207819 0.396545 0.786754 11.00000 0.03220 0.02985 = 0.03352 0.01165 0.01774 0.01761 O2 4 0.464748 0.513898 0.847820 11.00000 0.03759 0.01551 = 0.02590 0.00271 0.00444 -0.00017 O3 4 0.311509 0.100280 1.035760 11.00000 0.03316 0.03490 = 0.02099 0.01154 0.00967 0.01660 O4 4 0.087823 -0.034919 0.858427 11.00000 0.03126 0.01960 = 0.03320 0.00552 0.01452 0.00128 O5 4 0.511981 0.238054 0.830950 11.00000 0.01767 0.01811 = 0.02521 0.00058 0.00382 0.00299 N1 3 0.453095 0.113513 0.716054 11.00000 0.02000 0.01686 = 0.02150 0.00317 0.00731 0.00387 AFIX 13 H1 2 0.407190 0.130055 0.635844 11.00000 -1.20000 AFIX 0 C1 1 0.470075 0.358336 0.587767 11.00000 0.02934 0.03391 = 0.03108 0.01215 0.01360 0.01017 AFIX 43 H1A 2 0.555437 0.403395 0.653838 11.00000 -1.20000 AFIX 0 C2 1 0.466954 0.312296 0.458400 11.00000 0.05670 0.05114 = 0.04052 0.02305 0.03310 0.02929 AFIX 43 H2 2 0.550827 0.325552 0.437120 11.00000 -1.20000 AFIX 0 C3 1 0.340605 0.247203 0.361499 11.00000 0.07858 0.04476 = 0.02399 0.01379 0.02270 0.03663 AFIX 43 H3 2 0.339583 0.215898 0.274863 11.00000 -1.20000 AFIX 0 C4 1 0.215014 0.227534 0.390798 11.00000 0.05607 0.04150 = 0.02215 0.00380 -0.00360 0.01859 AFIX 43 H4 2 0.129891 0.185006 0.323852 11.00000 -1.20000 AFIX 0 C5 1 0.215313 0.271236 0.520511 11.00000 0.02812 0.03189 = 0.02648 0.00629 0.00285 0.01036 AFIX 43 H5 2 0.131236 0.257063 0.541401 11.00000 -1.20000 AFIX 0 C6 1 0.343511 0.336147 0.617408 11.00000 0.02538 0.01863 = 0.01952 0.00606 0.00805 0.00862 C7 1 0.390654 0.267692 0.856198 11.00000 0.02065 0.01732 = 0.01700 0.00423 0.00596 0.00505 AFIX 13 H7 2 0.410799 0.304981 0.951230 11.00000 -1.20000 AFIX 0 C8 1 0.272018 0.133082 0.805373 11.00000 0.01929 0.01635 = 0.01520 0.00333 0.00550 0.00410 AFIX 13 H8 2 0.197833 0.131625 0.729991 11.00000 -1.20000 AFIX 0 C9 1 0.351862 0.030529 0.761034 11.00000 0.02167 0.01623 = 0.01828 0.00379 0.00771 0.00488 AFIX 13 H9 2 0.403192 0.010999 0.837291 11.00000 -1.20000 AFIX 0 C10 1 0.572937 0.062614 0.706109 11.00000 0.02398 0.02716 = 0.04281 0.00629 0.01580 0.00909 AFIX 137 H10A 2 0.642630 0.127895 0.691021 11.00000 -1.50000 H10B 2 0.541744 -0.020370 0.634552 11.00000 -1.50000 H10C 2 0.613470 0.046751 0.786198 11.00000 -1.50000 AFIX 0 C11 1 0.115096 0.215375 0.981026 11.00000 0.02357 0.02208 = 0.01890 0.00703 0.01013 0.00728 C12 1 -0.029859 0.188469 0.927913 11.00000 0.02354 0.02803 = 0.02326 0.00768 0.00789 0.00491 AFIX 43 H12 2 -0.082242 0.109450 0.859489 11.00000 -1.20000 AFIX 0 C13 1 -0.095161 0.281113 0.978415 11.00000 0.02339 0.03935 = 0.03502 0.01381 0.01223 0.01267 AFIX 43 H13 2 -0.192007 0.264702 0.943344 11.00000 -1.20000 AFIX 0 C14 1 -0.016757 0.398049 1.080915 11.00000 0.03699 0.03567 = 0.03501 0.01120 0.01924 0.01961 AFIX 43 H14 2 -0.061332 0.459219 1.115485 11.00000 -1.20000 AFIX 0 C15 1 0.127879 0.424227 1.132146 11.00000 0.03495 0.02884 = 0.02897 0.00071 0.01067 0.00995 AFIX 43 H15 2 0.180129 0.503619 1.200149 11.00000 -1.20000 AFIX 0 C16 1 0.195252 0.333081 1.082874 11.00000 0.02440 0.02706 = 0.02294 0.00375 0.00804 0.00721 AFIX 43 H16 2 0.292318 0.350329 1.117304 11.00000 -1.20000 AFIX 0 C17 1 0.265842 -0.100290 0.653616 11.00000 0.02116 0.01856 = 0.02431 0.00020 0.01138 0.00310 C18 1 0.206968 -0.097892 0.527916 11.00000 0.02897 0.03281 = 0.02429 0.00126 0.01075 0.00027 AFIX 43 H18 2 0.218000 -0.015786 0.511740 11.00000 -1.20000 AFIX 0 C19 1 0.131454 -0.217773 0.425860 11.00000 0.02994 0.05238 = 0.02590 -0.00824 0.01206 -0.00490 AFIX 43 H19 2 0.092741 -0.215867 0.341760 11.00000 -1.20000 AFIX 0 C20 1 0.114727 -0.338783 0.450633 11.00000 0.03014 0.03301 = 0.05240 -0.01841 0.02014 -0.00672 AFIX 43 H20 2 0.064408 -0.419036 0.383050 11.00000 -1.20000 AFIX 0 C21 1 0.172303 -0.341542 0.575325 11.00000 0.03122 0.01821 = 0.06790 -0.00142 0.02459 0.00149 AFIX 43 H21 2 0.159133 -0.424192 0.590515 11.00000 -1.20000 AFIX 0 C22 1 0.250096 -0.223275 0.679766 11.00000 0.02324 0.01966 = 0.04582 0.00595 0.01807 0.00685 C23 1 0.313941 -0.231943 0.812848 11.00000 0.04100 0.02793 = 0.06239 0.02481 0.02184 0.01521 AFIX 137 H23A 2 0.415062 -0.199836 0.836730 11.00000 -1.50000 H23B 2 0.285937 -0.324104 0.811016 11.00000 -1.50000 H23C 2 0.281674 -0.177434 0.875947 11.00000 -1.50000 AFIX 0 HKLF 4 REM sa3397 in P-1 REM R1 = 0.0373 for 4756 Fo > 4sig(Fo) and 0.0397 for all 4958 data REM 282 parameters refined using 0 restraints END WGHT 0.0391 0.5925 REM Highest difference peak 0.348, deepest hole -0.794, 1-sigma level 0.046 Q1 1 0.3084 -0.0386 0.7033 11.00000 0.05 0.35 Q2 1 0.3496 0.3631 0.6901 11.00000 0.05 0.34 Q3 1 0.1486 0.1662 0.9594 11.00000 0.05 0.31 Q4 1 0.3746 0.3163 0.8193 11.00000 0.05 0.30 Q5 1 0.3052 0.0796 0.7857 11.00000 0.05 0.30 Q6 1 0.1589 0.2728 1.0236 11.00000 0.05 0.29 Q7 1 0.2409 0.1176 0.8597 11.00000 0.05 0.29 Q8 1 0.3290 0.2054 0.8306 11.00000 0.05 0.27 Q9 1 0.3969 0.3428 0.5979 11.00000 0.05 0.26 Q10 1 0.0490 0.2025 0.9688 11.00000 0.05 0.23 Q11 1 0.2258 -0.2817 0.6250 11.00000 0.05 0.23 Q12 1 0.1621 -0.1627 0.4850 11.00000 0.05 0.22 Q13 1 0.2878 0.2904 0.5734 11.00000 0.05 0.22 Q14 1 -0.0600 0.2226 0.9745 11.00000 0.05 0.22 Q15 1 0.2361 -0.0971 0.5951 11.00000 0.05 0.21 Q16 1 0.2635 -0.1596 0.6706 11.00000 0.05 0.20 Q17 1 0.0590 0.4175 1.0881 11.00000 0.05 0.20 Q18 1 0.4000 0.0608 0.7414 11.00000 0.05 0.20 Q19 1 -0.0490 0.3484 1.0276 11.00000 0.05 0.19 Q20 1 0.4574 0.3284 0.5204 11.00000 0.05 0.19 ; _shelx_res_checksum 34439 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 S1 S 0.34738(4) 0.39340(3) 0.78193(3) 0.01947(9) Uani 1 1 d . S2 S 0.19617(4) 0.09145(3) 0.92666(3) 0.01972(9) Uani 1 1 d . O1 O 0.20782(12) 0.39655(12) 0.78675(11) 0.0287(2) Uani 1 1 d . O2 O 0.46475(13) 0.51390(11) 0.84782(11) 0.0294(3) Uani 1 1 d . O3 O 0.31151(12) 0.10028(12) 1.03576(10) 0.0278(2) Uani 1 1 d . O4 O 0.08782(12) -0.03492(11) 0.85843(11) 0.0288(2) Uani 1 1 d . O5 O 0.51198(10) 0.23805(10) 0.83095(10) 0.0225(2) Uani 1 1 d . N1 N 0.45310(13) 0.11351(12) 0.71605(12) 0.0201(2) Uani 1 1 d . H1 H 0.4072 0.1301 0.6358 0.024 Uiso 1 1 calc R C1 C 0.47008(18) 0.35834(17) 0.58777(17) 0.0302(3) Uani 1 1 d . H1A H 0.5554 0.4034 0.6538 0.036 Uiso 1 1 calc R C2 C 0.4670(2) 0.3123(2) 0.4584(2) 0.0422(5) Uani 1 1 d . H2 H 0.5508 0.3256 0.4371 0.051 Uiso 1 1 calc R C3 C 0.3406(3) 0.2472(2) 0.36150(18) 0.0442(5) Uani 1 1 d . H3 H 0.3396 0.2159 0.2749 0.053 Uiso 1 1 calc R C4 C 0.2150(2) 0.2275(2) 0.39080(18) 0.0433(5) Uani 1 1 d . H4 H 0.1299 0.1850 0.3239 0.052 Uiso 1 1 calc R C5 C 0.21531(18) 0.27124(17) 0.52051(16) 0.0302(3) Uani 1 1 d . H5 H 0.1312 0.2571 0.5414 0.036 Uiso 1 1 calc R C6 C 0.34351(16) 0.33615(14) 0.61741(14) 0.0206(3) Uani 1 1 d . C7 C 0.39065(15) 0.26769(14) 0.85620(14) 0.0186(3) Uani 1 1 d . H7 H 0.4108 0.3050 0.9512 0.022 Uiso 1 1 calc R C8 C 0.27202(14) 0.13308(14) 0.80537(13) 0.0174(3) Uani 1 1 d . H8 H 0.1978 0.1316 0.7300 0.021 Uiso 1 1 calc R C9 C 0.35186(15) 0.03053(14) 0.76103(14) 0.0189(3) Uani 1 1 d . H9 H 0.4032 0.0110 0.8373 0.023 Uiso 1 1 calc R C10 C 0.57294(17) 0.06261(17) 0.70611(18) 0.0310(4) Uani 1 1 d . H10A H 0.6426 0.1279 0.6910 0.047 Uiso 1 1 calc GR H10B H 0.5417 -0.0204 0.6346 0.047 Uiso 1 1 calc GR H10C H 0.6135 0.0468 0.7862 0.047 Uiso 1 1 calc GR C11 C 0.11510(15) 0.21537(15) 0.98103(14) 0.0207(3) Uani 1 1 d . C12 C -0.02986(16) 0.18847(16) 0.92791(15) 0.0254(3) Uani 1 1 d . H12 H -0.0822 0.1095 0.8595 0.030 Uiso 1 1 calc R C13 C -0.09516(17) 0.28111(18) 0.97841(17) 0.0310(4) Uani 1 1 d . H13 H -0.1920 0.2647 0.9433 0.037 Uiso 1 1 calc R C14 C -0.01676(19) 0.39805(18) 1.08092(17) 0.0329(4) Uani 1 1 d . H14 H -0.0613 0.4592 1.1155 0.040 Uiso 1 1 calc R C15 C 0.12788(19) 0.42423(17) 1.13215(17) 0.0324(4) Uani 1 1 d . H15 H 0.1801 0.5036 1.2001 0.039 Uiso 1 1 calc R C16 C 0.19525(17) 0.33308(16) 1.08287(15) 0.0256(3) Uani 1 1 d . H16 H 0.2923 0.3503 1.1173 0.031 Uiso 1 1 calc R C17 C 0.26584(15) -0.10029(14) 0.65362(15) 0.0223(3) Uani 1 1 d . C18 C 0.20697(17) -0.09789(18) 0.52792(16) 0.0313(4) Uani 1 1 d . H18 H 0.2180 -0.0158 0.5117 0.038 Uiso 1 1 calc R C19 C 0.13145(19) -0.2178(2) 0.42586(18) 0.0424(5) Uani 1 1 d . H19 H 0.0927 -0.2159 0.3418 0.051 Uiso 1 1 calc R C20 C 0.1147(2) -0.33878(19) 0.4506(2) 0.0462(5) Uani 1 1 d . H20 H 0.0644 -0.4190 0.3831 0.055 Uiso 1 1 calc R C21 C 0.17230(19) -0.34154(17) 0.5753(2) 0.0414(5) Uani 1 1 d . H21 H 0.1591 -0.4242 0.5905 0.050 Uiso 1 1 calc R C22 C 0.25010(17) -0.22328(16) 0.67977(18) 0.0290(3) Uani 1 1 d . C23 C 0.3139(2) -0.23194(18) 0.8128(2) 0.0398(4) Uani 1 1 d . H23A H 0.4151 -0.1998 0.8367 0.060 Uiso 1 1 calc GR H23B H 0.2859 -0.3241 0.8110 0.060 Uiso 1 1 calc GR H23C H 0.2817 -0.1774 0.8759 0.060 Uiso 1 1 calc GR 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 0.02391(18) 0.01519(17) 0.01869(17) 0.00334(13) 0.00770(13) 0.00571(13) S2 0.02268(18) 0.01898(17) 0.01834(17) 0.00573(13) 0.00844(13) 0.00574(13) O1 0.0322(6) 0.0299(6) 0.0335(6) 0.0117(5) 0.0177(5) 0.0176(5) O2 0.0376(6) 0.0155(5) 0.0259(6) 0.0027(4) 0.0044(5) -0.0002(5) O3 0.0332(6) 0.0349(6) 0.0210(5) 0.0115(5) 0.0097(5) 0.0166(5) O4 0.0313(6) 0.0196(5) 0.0332(6) 0.0055(4) 0.0145(5) 0.0013(4) O5 0.0177(5) 0.0181(5) 0.0252(5) 0.0006(4) 0.0038(4) 0.0030(4) N1 0.0200(6) 0.0169(6) 0.0215(6) 0.0032(5) 0.0073(5) 0.0039(5) C1 0.0293(8) 0.0339(9) 0.0311(8) 0.0121(7) 0.0136(7) 0.0102(7) C2 0.0567(12) 0.0511(12) 0.0405(10) 0.0231(9) 0.0331(10) 0.0293(10) C3 0.0786(15) 0.0448(11) 0.0240(9) 0.0138(8) 0.0227(9) 0.0366(11) C4 0.0561(12) 0.0415(10) 0.0221(8) 0.0038(7) -0.0036(8) 0.0186(9) C5 0.0281(8) 0.0319(8) 0.0265(8) 0.0063(7) 0.0029(6) 0.0104(7) C6 0.0254(7) 0.0186(7) 0.0195(7) 0.0061(5) 0.0081(6) 0.0086(6) C7 0.0206(7) 0.0173(6) 0.0170(6) 0.0042(5) 0.0060(5) 0.0050(5) C8 0.0193(6) 0.0163(6) 0.0152(6) 0.0033(5) 0.0055(5) 0.0041(5) C9 0.0217(7) 0.0162(6) 0.0183(6) 0.0038(5) 0.0077(5) 0.0049(5) C10 0.0240(8) 0.0272(8) 0.0428(10) 0.0063(7) 0.0158(7) 0.0091(6) C11 0.0236(7) 0.0221(7) 0.0189(7) 0.0070(5) 0.0101(6) 0.0073(6) C12 0.0235(7) 0.0280(8) 0.0233(7) 0.0077(6) 0.0079(6) 0.0049(6) C13 0.0234(8) 0.0394(9) 0.0350(9) 0.0138(7) 0.0122(7) 0.0127(7) C14 0.0370(9) 0.0357(9) 0.0350(9) 0.0112(7) 0.0192(7) 0.0196(7) C15 0.0349(9) 0.0288(8) 0.0290(8) 0.0007(7) 0.0107(7) 0.0099(7) C16 0.0244(7) 0.0271(8) 0.0229(7) 0.0038(6) 0.0080(6) 0.0072(6) C17 0.0212(7) 0.0186(7) 0.0243(7) 0.0002(5) 0.0114(6) 0.0031(5) C18 0.0290(8) 0.0328(9) 0.0243(8) 0.0013(7) 0.0108(6) 0.0003(7) C19 0.0299(9) 0.0524(12) 0.0259(9) -0.0082(8) 0.0121(7) -0.0049(8) C20 0.0301(9) 0.0330(10) 0.0524(12) -0.0184(8) 0.0201(9) -0.0067(7) C21 0.0312(9) 0.0182(8) 0.0679(14) -0.0014(8) 0.0246(9) 0.0015(7) C22 0.0232(7) 0.0197(7) 0.0458(10) 0.0060(7) 0.0181(7) 0.0068(6) C23 0.0410(10) 0.0279(9) 0.0624(13) 0.0248(9) 0.0218(9) 0.0152(8) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 S1 C6 109.24(8) O1 S1 C7 106.85(7) O2 S1 O1 119.55(7) O2 S1 C6 107.72(8) O2 S1 C7 105.73(7) C6 S1 C7 107.11(7) O3 S2 C8 106.96(7) O3 S2 C11 108.09(7) O4 S2 O3 119.41(8) O4 S2 C8 105.58(7) O4 S2 C11 108.28(7) C11 S2 C8 108.04(7) C7 O5 N1 103.46(10) C9 N1 O5 100.56(10) C10 N1 O5 104.86(11) C10 N1 C9 113.10(12) C2 C1 C6 118.91(17) C3 C2 C1 120.17(18) C2 C3 C4 120.84(17) C3 C4 C5 120.14(18) C6 C5 C4 118.44(17) C1 C6 S1 118.98(12) C5 C6 S1 119.55(12) C5 C6 C1 121.48(15) O5 C7 S1 110.23(10) O5 C7 C8 107.11(11) C8 C7 S1 113.75(10) C7 C8 S2 114.94(10) C7 C8 C9 101.48(11) C9 C8 S2 109.45(10) N1 C9 C8 99.62(11) N1 C9 C17 111.00(11) C17 C9 C8 117.15(12) C12 C11 S2 119.09(12) C16 C11 S2 119.36(12) C16 C11 C12 121.36(14) C13 C12 C11 118.99(15) C14 C13 C12 120.22(15) C13 C14 C15 120.20(16) C16 C15 C14 120.49(16) C15 C16 C11 118.73(15) C18 C17 C9 119.34(14) C18 C17 C22 120.51(15) C22 C17 C9 120.11(14) C17 C18 C19 120.48(18) C20 C19 C18 119.47(19) C19 C20 C21 120.23(17) C20 C21 C22 121.82(18) C17 C22 C23 122.73(15) C21 C22 C17 117.49(17) C21 C22 C23 119.78(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.4421(12) S1 O2 1.4397(13) S1 C6 1.7580(15) S1 C7 1.8255(15) S2 O3 1.4410(13) S2 O4 1.4368(13) S2 C8 1.8019(15) S2 C11 1.7629(16) O5 N1 1.4811(16) O5 C7 1.4117(17) N1 C9 1.4740(18) N1 C10 1.4557(19) C1 C2 1.383(2) C1 C6 1.390(2) C2 C3 1.370(3) C3 C4 1.378(3) C4 C5 1.393(3) C5 C6 1.382(2) C7 C8 1.540(2) C8 C9 1.5520(19) C9 C17 1.510(2) C11 C12 1.389(2) C11 C16 1.389(2) C12 C13 1.385(2) C13 C14 1.384(3) C14 C15 1.385(3) C15 C16 1.384(2) C17 C18 1.390(2) C17 C22 1.403(2) C18 C19 1.395(2) C19 C20 1.375(3) C20 C21 1.379(3) C21 C22 1.401(2) C22 C23 1.500(3) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion S1 C7 C8 S2 -115.81(10) S1 C7 C8 C9 126.21(10) S2 C8 C9 N1 -155.34(9) S2 C8 C9 C17 84.96(13) S2 C11 C12 C13 174.65(12) S2 C11 C16 C15 -174.49(13) O1 S1 C6 C1 163.13(12) O1 S1 C6 C5 -16.38(15) O1 S1 C7 O5 167.76(9) O1 S1 C7 C8 47.45(12) O2 S1 C6 C1 31.84(14) O2 S1 C6 C5 -147.67(13) O2 S1 C7 O5 -63.88(11) O2 S1 C7 C8 175.81(10) O3 S2 C8 C7 -52.77(12) O3 S2 C8 C9 60.62(11) O3 S2 C11 C12 -146.23(12) O3 S2 C11 C16 28.79(14) O4 S2 C8 C7 179.06(10) O4 S2 C8 C9 -67.54(11) O4 S2 C11 C12 -15.54(14) O4 S2 C11 C16 159.48(12) O5 N1 C9 C8 50.46(12) O5 N1 C9 C17 174.57(11) O5 C7 C8 S2 122.14(11) O5 C7 C8 C9 4.15(13) N1 O5 C7 S1 -97.22(10) N1 O5 C7 C8 27.01(13) N1 C9 C17 C18 -46.24(18) N1 C9 C17 C22 131.46(14) C1 C2 C3 C4 0.6(3) C2 C1 C6 S1 179.50(13) C2 C1 C6 C5 -1.0(2) C2 C3 C4 C5 -1.5(3) C3 C4 C5 C6 1.1(3) C4 C5 C6 S1 179.62(13) C4 C5 C6 C1 0.1(2) C6 S1 C7 O5 50.80(11) C6 S1 C7 C8 -69.51(12) C6 C1 C2 C3 0.7(3) C7 S1 C6 C1 -81.49(14) C7 S1 C6 C5 99.00(14) C7 O5 N1 C9 -49.59(12) C7 O5 N1 C10 -167.13(12) C7 C8 C9 N1 -33.47(12) C7 C8 C9 C17 -153.16(12) C8 S2 C11 C12 98.35(13) C8 S2 C11 C16 -86.63(13) C8 C9 C17 C18 67.21(18) C8 C9 C17 C22 -115.09(15) C9 C17 C18 C19 177.62(14) C9 C17 C22 C21 -178.31(14) C9 C17 C22 C23 1.0(2) C10 N1 C9 C8 161.75(12) C10 N1 C9 C17 -74.13(16) C11 S2 C8 C7 63.38(12) C11 S2 C8 C9 176.77(9) C11 C12 C13 C14 -0.5(2) C12 C11 C16 C15 0.4(2) C12 C13 C14 C15 1.1(3) C13 C14 C15 C16 -0.9(3) C14 C15 C16 C11 0.2(3) C16 C11 C12 C13 -0.3(2) C17 C18 C19 C20 0.4(3) C18 C17 C22 C21 -0.6(2) C18 C17 C22 C23 178.68(15) C18 C19 C20 C21 -0.1(3) C19 C20 C21 C22 -0.7(3) C20 C21 C22 C17 1.0(2) C20 C21 C22 C23 -178.34(16) C22 C17 C18 C19 -0.1(2)