#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:20:18 +0300 (Wed, 13 May 2020) $ #$Revision: 251999 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038354.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_4038354 loop_ _publ_author_name 'Ruggeri, Michele' 'Dombrowski, Amanda W.' 'Djuric, Stevan W.' 'Baxendale, Ian R.' _publ_section_title ; A rearrangement of 3-hydroxyazetidines into 2-oxazolines. ; _journal_name_full 'The Journal of organic chemistry' _journal_paper_doi 10.1021/acs.joc.0c00656 _journal_year 2020 _chemical_formula_moiety 'C18 H20 N2 O3 S, 0.5(C4 H8 O2)' _chemical_formula_sum 'C20 H24 N2 O4 S' _chemical_formula_weight 388.47 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2017-02-22 _audit_creation_method ; Olex2 1.2-beta (compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292) ; _cell_angle_alpha 90 _cell_angle_beta 90.544(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.4987(8) _cell_length_b 11.7051(6) _cell_length_c 21.9098(11) _cell_measurement_reflns_used 9829 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.96 _cell_measurement_theta_min 2.38 _cell_volume 3974.6(4) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_collection 'APEX3 v.2016.1-0 (Bruker, 2016)' _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 'ShelXL 2014/7 multi-CPU (Sheldrick, 2015)' _computing_structure_solution 'ShelXS 2013/1 (Sheldrick, 2008)' _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 10.4 _diffrn_detector_type 'Bruker PHOTON 100 CMOS' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device '3-circle area detector diffractometer' _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_unetI/netI 0.0308 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 36410 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 27.499 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_min 2.365 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\mS microsource' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9616 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1054 before and 0.0602 after correction. The Ratio of minimum to maximum transmission is 0.9616. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.298 _exptl_crystal_description block _exptl_crystal_F_000 1648 _exptl_crystal_size_max 0.292 _exptl_crystal_size_mid 0.275 _exptl_crystal_size_min 0.219 _refine_diff_density_max 0.369 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef 0.00054(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 4566 _refine_ls_number_restraints 30 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0419 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+5.1750P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.1041 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3652 _reflns_number_total 4566 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 17srv053.cif _cod_data_source_block 17srv053 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 4038354 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Rigid body (RIGU) restrains O4, C21, C19, O5, C20, C22 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 3. Others Uiso(H7A)=Uiso(H7B)=Uiso(H7C)=FVAR(1) Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=FVAR(2) Fixed Sof: O4(0.5) O5(0.5) C19(0.5) C20(0.5) H20A(0.5) H20B(0.5) H20C(0.5) C21(0.5) H21A(0.5) H21B(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5) 4.a Rotating group: C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C) 4.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C10(H10A,H10B), C21(H21A,H21B) 4.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16) 4.d Idealised Me refined as rotating group: C7(H7A,H7B,H7C) ; _oslims_operator_name 'Dr A Batsanov' _oslims_operator_uuid 642c0cab-15e1-4db6-aabf-d1e3f44b6814 _oslims_submitter_name 'Mr Michele Ruggeri' _oslims_submitter_uuid 1a56f251-525c-414f-9d37-3e740585b168 _shelx_estimated_absorpt_t_min 0.946 _shelx_estimated_absorpt_t_max 0.959 _shelx_res_checksum 83336 _shelx_res_file ; 17srv053.res created by SHELXL-2014/7 TITL 17srv053 in C2/c #15 REM reset to C2/c #15 CELL 0.71073 15.4987 11.7051 21.9098 90 90.5444 90 ZERR 8 0.0008 0.0006 0.0011 0 0.0021 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O S UNIT 160 192 16 32 8 EQIV $1 1-X,+Y,0.5-Z RIGU O4 C21 C19 O5 C20 C22 L.S. 7 PLAN 6 SIZE 0.219 0.275 0.292 TEMP -153.15 HTAB N1 N2_$1 HTAB C22 O4_$1 BOND fmap 2 53 acta 55 OMIT -3 55 REM REM REM WGHT 0.046000 5.175000 EXTI 0.000542 FVAR 0.07283 0.04868 0.07275 S 5 0.637423 0.480435 0.111134 11.00000 0.01920 0.02452 = 0.01140 0.00071 0.00063 -0.00164 O1 4 0.728334 0.460899 0.118016 11.00000 0.01960 0.03798 = 0.02122 0.00431 0.00232 0.00147 O2 4 0.585074 0.402943 0.075986 11.00000 0.02982 0.02419 = 0.01531 -0.00110 -0.00090 -0.00283 O3 4 0.681225 0.263936 0.289785 11.00000 0.02537 0.02021 = 0.02452 0.00299 0.00359 0.00469 N1 3 0.596056 0.481229 0.178179 11.00000 0.01847 0.02869 = 0.01131 0.00002 0.00022 -0.00532 H1 2 0.543405 0.463038 0.180891 11.00000 0.02972 N2 3 0.581540 0.401661 0.303221 11.00000 0.01594 0.02036 = 0.01298 0.00023 -0.00048 -0.00132 C1 1 0.627382 0.617244 0.077606 11.00000 0.02132 0.02437 = 0.01097 0.00045 0.00178 -0.00439 C2 1 0.559389 0.641170 0.038120 11.00000 0.02080 0.02644 = 0.01575 -0.00066 -0.00043 -0.00583 AFIX 43 H2 2 0.516548 0.585042 0.029922 11.00000 -1.20000 AFIX 0 C3 1 0.554414 0.747809 0.010658 11.00000 0.02402 0.02883 = 0.01718 0.00302 -0.00054 -0.00159 AFIX 43 H3 2 0.507634 0.764150 -0.016281 11.00000 -1.20000 AFIX 0 C4 1 0.616375 0.831145 0.021723 11.00000 0.02897 0.02645 = 0.01958 0.00031 0.00753 -0.00247 C5 1 0.683906 0.805555 0.061943 11.00000 0.02929 0.03044 = 0.02562 -0.00079 0.00120 -0.01354 AFIX 43 H5 2 0.726494 0.861869 0.070440 11.00000 -1.20000 AFIX 0 C6 1 0.690036 0.699655 0.089706 11.00000 0.02412 0.03424 = 0.01977 0.00061 -0.00420 -0.00820 AFIX 43 H6 2 0.736624 0.683300 0.116810 11.00000 -1.20000 AFIX 0 C7 1 0.612619 0.945762 -0.009422 11.00000 0.03813 0.02756 = 0.03737 0.00410 0.00690 -0.00297 AFIX 137 H7A 2 0.561382 0.949274 -0.035912 11.00000 21.00000 H7B 2 0.664491 0.956336 -0.034022 11.00000 21.00000 H7C 2 0.609540 1.006256 0.021403 11.00000 21.00000 AFIX 0 C8 1 0.635705 0.542511 0.229147 11.00000 0.02431 0.02026 = 0.01244 0.00020 -0.00193 -0.00185 AFIX 23 H8A 2 0.595309 0.601941 0.243612 11.00000 -1.20000 H8B 2 0.688565 0.581304 0.214869 11.00000 -1.20000 AFIX 0 C9 1 0.659233 0.462915 0.282648 11.00000 0.01535 0.01907 = 0.01210 0.00027 0.00070 -0.00025 C10 1 0.721126 0.365512 0.264653 11.00000 0.01914 0.02241 = 0.01794 -0.00164 0.00210 0.00155 AFIX 23 H10A 2 0.726012 0.359725 0.219739 11.00000 -1.20000 H10B 2 0.779299 0.377733 0.282533 11.00000 -1.20000 AFIX 0 C11 1 0.695407 0.536061 0.334661 11.00000 0.01822 0.01681 = 0.01310 0.00140 -0.00138 0.00118 C12 1 0.772884 0.593298 0.326439 11.00000 0.02218 0.02809 = 0.01729 -0.00116 0.00465 -0.00435 AFIX 43 H12 2 0.803203 0.584678 0.289241 11.00000 -1.20000 AFIX 0 C13 1 0.806297 0.662711 0.371891 11.00000 0.02408 0.03571 = 0.02990 -0.00668 0.00223 -0.01248 AFIX 43 H13 2 0.858817 0.702625 0.365515 11.00000 -1.20000 AFIX 0 C14 1 0.763575 0.674162 0.426472 11.00000 0.03480 0.03615 = 0.02349 -0.01030 -0.00064 -0.01064 AFIX 43 H14 2 0.786750 0.721697 0.457715 11.00000 -1.20000 AFIX 0 C15 1 0.687174 0.616545 0.435664 11.00000 0.03188 0.03911 = 0.01602 -0.00720 0.00464 -0.00488 AFIX 43 H15 2 0.657976 0.623814 0.473394 11.00000 -1.20000 AFIX 0 C16 1 0.652939 0.547930 0.389783 11.00000 0.02135 0.02685 = 0.01635 -0.00088 0.00225 -0.00382 AFIX 43 H16 2 0.600075 0.508825 0.396158 11.00000 -1.20000 AFIX 0 C17 1 0.601062 0.296759 0.307276 11.00000 0.02127 0.02181 = 0.01578 -0.00005 -0.00092 -0.00010 C18 1 0.546327 0.204269 0.331616 11.00000 0.03816 0.02513 = 0.04548 0.00551 0.00927 -0.00482 AFIX 7 H18A 2 0.535827 0.147210 0.299666 11.00000 31.00000 H18B 2 0.491167 0.236199 0.344927 11.00000 31.00000 H18C 2 0.575687 0.168069 0.366366 11.00000 31.00000 AFIX 0 PART -1 O4 4 0.451625 0.967086 0.247365 10.50000 0.07593 0.02972 = 0.05422 -0.00606 -0.00354 0.01123 O5 4 0.486736 0.786613 0.261417 10.50000 0.05353 0.02535 = 0.03608 0.00206 -0.00566 -0.00814 C19 1 0.464340 0.873582 0.226558 10.50000 0.04299 0.02433 = 0.03097 0.00069 0.00229 0.00113 C20 1 0.452085 0.838190 0.161746 10.50000 0.09096 0.04870 = 0.03404 -0.00321 -0.00862 0.01815 AFIX 7 H20A 2 0.433711 0.757986 0.160321 10.50000 -1.50000 H20B 2 0.407766 0.886118 0.142243 10.50000 -1.50000 H20C 2 0.506568 0.846527 0.139716 10.50000 -1.50000 AFIX 0 C21 1 0.500166 0.808386 0.326867 10.50000 0.03929 0.05419 = 0.02724 0.00288 0.00210 -0.01546 AFIX 23 H21A 2 0.490052 0.736915 0.349876 10.50000 -1.20000 H21B 2 0.457673 0.865704 0.340742 10.50000 -1.20000 AFIX 0 C22 1 0.588015 0.850245 0.340402 10.50000 0.03762 0.03121 = 0.03824 -0.00258 -0.00246 -0.00569 AFIX 7 H22A 2 0.594480 0.862085 0.384493 10.50000 -1.50000 H22B 2 0.630385 0.793844 0.326762 10.50000 -1.50000 H22C 2 0.597499 0.922705 0.319091 10.50000 -1.50000 AFIX 0 HKLF 4 REM 17srv053 in C2/c #15 REM R1 = 0.0419 for 3652 Fo > 4sig(Fo) and 0.0590 for all 4566 data REM 282 parameters refined using 30 restraints END WGHT 0.0462 5.2024 REM Highest difference peak 0.369, deepest hole -0.350, 1-sigma level 0.051 Q1 1 0.6282 0.5600 0.0972 11.00000 0.05 0.37 Q2 1 0.4950 0.9813 0.2772 11.00000 0.05 0.29 Q3 1 0.6430 0.4978 0.2564 11.00000 0.05 0.29 Q4 1 0.6824 0.4872 0.3139 11.00000 0.05 0.28 Q5 1 0.6923 0.4181 0.2750 11.00000 0.05 0.27 Q6 1 0.6201 0.5123 0.2024 11.00000 0.05 0.26 ; _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 S S 0.63742(3) 0.48044(4) 0.11113(2) 0.01837(12) Uani 1 1 d . . . . . O1 O 0.72833(8) 0.46090(11) 0.11802(5) 0.0263(3) Uani 1 1 d . . . . . O2 O 0.58507(8) 0.40294(10) 0.07599(5) 0.0231(3) Uani 1 1 d . . . . . O3 O 0.68122(8) 0.26394(10) 0.28979(5) 0.0233(3) Uani 1 1 d . . . . . N1 N 0.59606(9) 0.48123(13) 0.17818(6) 0.0195(3) Uani 1 1 d . . . . . H1 H 0.5434(14) 0.4630(18) 0.1809(9) 0.030(6) Uiso 1 1 d . . . . . N2 N 0.58154(8) 0.40166(11) 0.30322(6) 0.0164(3) Uani 1 1 d . . . . . C1 C 0.62738(10) 0.61724(14) 0.07761(7) 0.0189(3) Uani 1 1 d . . . . . C2 C 0.55939(11) 0.64117(15) 0.03812(7) 0.0210(4) Uani 1 1 d . . . . . H2 H 0.5165 0.5850 0.0299 0.025 Uiso 1 1 calc R . . . . C3 C 0.55441(11) 0.74781(15) 0.01066(8) 0.0233(4) Uani 1 1 d . . . . . H3 H 0.5076 0.7642 -0.0163 0.028 Uiso 1 1 calc R . . . . C4 C 0.61637(11) 0.83114(15) 0.02172(8) 0.0250(4) Uani 1 1 d . . . . . C5 C 0.68391(12) 0.80555(16) 0.06194(8) 0.0284(4) Uani 1 1 d . . . . . H5 H 0.7265 0.8619 0.0704 0.034 Uiso 1 1 calc R . . . . C6 C 0.69004(11) 0.69966(16) 0.08971(8) 0.0261(4) Uani 1 1 d . . . . . H6 H 0.7366 0.6833 0.1168 0.031 Uiso 1 1 calc R . . . . C7 C 0.61262(13) 0.94576(17) -0.00942(10) 0.0343(5) Uani 1 1 d . . . . . H7A H 0.5614 0.9493 -0.0359 0.049(4) Uiso 1 1 calc GR . . . . H7B H 0.6645 0.9563 -0.0340 0.049(4) Uiso 1 1 calc GR . . . . H7C H 0.6095 1.0063 0.0214 0.049(4) Uiso 1 1 calc GR . . . . C8 C 0.63570(11) 0.54251(14) 0.22915(7) 0.0190(3) Uani 1 1 d . . . . . H8A H 0.5953 0.6019 0.2436 0.023 Uiso 1 1 calc R . . . . H8B H 0.6886 0.5813 0.2149 0.023 Uiso 1 1 calc R . . . . C9 C 0.65923(10) 0.46292(13) 0.28265(7) 0.0155(3) Uani 1 1 d . . . . . C10 C 0.72113(10) 0.36551(14) 0.26465(7) 0.0198(3) Uani 1 1 d . . . . . H10A H 0.7260 0.3597 0.2197 0.024 Uiso 1 1 calc R . . . . H10B H 0.7793 0.3777 0.2825 0.024 Uiso 1 1 calc R . . . . C11 C 0.69541(10) 0.53606(13) 0.33466(7) 0.0161(3) Uani 1 1 d . . . . . C12 C 0.77288(11) 0.59330(15) 0.32644(8) 0.0225(4) Uani 1 1 d . . . . . H12 H 0.8032 0.5847 0.2892 0.027 Uiso 1 1 calc R . . . . C13 C 0.80630(12) 0.66271(17) 0.37189(9) 0.0299(4) Uani 1 1 d . . . . . H13 H 0.8588 0.7026 0.3655 0.036 Uiso 1 1 calc R . . . . C14 C 0.76358(12) 0.67416(17) 0.42647(8) 0.0315(4) Uani 1 1 d . . . . . H14 H 0.7868 0.7217 0.4577 0.038 Uiso 1 1 calc R . . . . C15 C 0.68717(12) 0.61655(17) 0.43566(8) 0.0290(4) Uani 1 1 d . . . . . H15 H 0.6580 0.6238 0.4734 0.035 Uiso 1 1 calc R . . . . C16 C 0.65294(11) 0.54793(15) 0.38978(7) 0.0215(4) Uani 1 1 d . . . . . H16 H 0.6001 0.5088 0.3962 0.026 Uiso 1 1 calc R . . . . C17 C 0.60106(10) 0.29676(14) 0.30728(7) 0.0196(3) Uani 1 1 d . . . . . C18 C 0.54633(13) 0.20427(17) 0.33162(10) 0.0362(5) Uani 1 1 d . . . . . H18A H 0.5358 0.1472 0.2997 0.073(5) Uiso 1 1 d GR . . . . H18B H 0.4912 0.2362 0.3449 0.073(5) Uiso 1 1 d GR . . . . H18C H 0.5757 0.1681 0.3664 0.073(5) Uiso 1 1 d GR . . . . O4 O 0.4516(2) 0.9671(3) 0.24736(16) 0.0533(9) Uani 0.5 1 d . U P A -1 O5 O 0.4867(3) 0.7866(2) 0.26142(18) 0.0384(10) Uani 0.5 1 d . U P A -1 C19 C 0.4643(3) 0.8736(3) 0.22656(18) 0.0327(8) Uani 0.5 1 d . U P A -1 C20 C 0.4521(6) 0.8382(7) 0.1617(3) 0.058(2) Uani 0.5 1 d . U P A -1 H20A H 0.4337 0.7580 0.1603 0.087 Uiso 0.5 1 d GR . P A -1 H20B H 0.4078 0.8861 0.1422 0.087 Uiso 0.5 1 d GR . P A -1 H20C H 0.5066 0.8465 0.1397 0.087 Uiso 0.5 1 d GR . P A -1 C21 C 0.5002(3) 0.8084(5) 0.3269(2) 0.0402(11) Uani 0.5 1 d . U P A -1 H21A H 0.4901 0.7369 0.3499 0.048 Uiso 0.5 1 calc R . P A -1 H21B H 0.4577 0.8657 0.3407 0.048 Uiso 0.5 1 calc R . P A -1 C22 C 0.5880(4) 0.8502(6) 0.3404(3) 0.0357(13) Uani 0.5 1 d . U P A -1 H22A H 0.5945 0.8621 0.3845 0.054 Uiso 0.5 1 d GR . P A -1 H22B H 0.6304 0.7938 0.3268 0.054 Uiso 0.5 1 d GR . P A -1 H22C H 0.5975 0.9227 0.3191 0.054 Uiso 0.5 1 d GR . P A -1 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 S 0.0192(2) 0.0245(2) 0.01140(19) 0.00071(15) 0.00063(14) -0.00164(16) O1 0.0196(6) 0.0380(8) 0.0212(6) 0.0043(5) 0.0023(5) 0.0015(5) O2 0.0298(7) 0.0242(6) 0.0153(6) -0.0011(5) -0.0009(5) -0.0028(5) O3 0.0254(6) 0.0202(6) 0.0245(6) 0.0030(5) 0.0036(5) 0.0047(5) N1 0.0185(7) 0.0287(8) 0.0113(6) 0.0000(6) 0.0002(5) -0.0053(6) N2 0.0159(7) 0.0204(7) 0.0130(6) 0.0002(5) -0.0005(5) -0.0013(5) C1 0.0213(8) 0.0244(8) 0.0110(7) 0.0004(6) 0.0018(6) -0.0044(7) C2 0.0208(8) 0.0264(9) 0.0157(8) -0.0007(7) -0.0004(6) -0.0058(7) C3 0.0240(9) 0.0288(9) 0.0172(8) 0.0030(7) -0.0005(7) -0.0016(7) C4 0.0290(9) 0.0265(9) 0.0196(8) 0.0003(7) 0.0075(7) -0.0025(7) C5 0.0293(10) 0.0304(10) 0.0256(9) -0.0008(8) 0.0012(7) -0.0135(8) C6 0.0241(9) 0.0342(10) 0.0198(8) 0.0006(7) -0.0042(7) -0.0082(7) C7 0.0381(11) 0.0276(10) 0.0374(11) 0.0041(8) 0.0069(9) -0.0030(8) C8 0.0243(9) 0.0203(8) 0.0124(7) 0.0002(6) -0.0019(6) -0.0019(6) C9 0.0154(7) 0.0191(8) 0.0121(7) 0.0003(6) 0.0007(6) -0.0002(6) C10 0.0191(8) 0.0224(9) 0.0179(8) -0.0016(6) 0.0021(6) 0.0016(6) C11 0.0182(8) 0.0168(8) 0.0131(7) 0.0014(6) -0.0014(6) 0.0012(6) C12 0.0222(9) 0.0281(9) 0.0173(8) -0.0012(7) 0.0047(6) -0.0043(7) C13 0.0241(9) 0.0357(11) 0.0299(10) -0.0067(8) 0.0022(7) -0.0125(8) C14 0.0348(10) 0.0361(11) 0.0235(9) -0.0103(8) -0.0006(8) -0.0106(8) C15 0.0319(10) 0.0391(11) 0.0160(8) -0.0072(8) 0.0046(7) -0.0049(8) C16 0.0213(9) 0.0268(9) 0.0163(8) -0.0009(7) 0.0023(6) -0.0038(7) C17 0.0213(8) 0.0218(8) 0.0158(8) 0.0000(6) -0.0009(6) -0.0001(6) C18 0.0382(11) 0.0251(10) 0.0455(12) 0.0055(9) 0.0093(9) -0.0048(8) O4 0.076(2) 0.0297(16) 0.054(2) -0.0061(14) -0.0035(18) 0.0112(14) O5 0.054(3) 0.0253(12) 0.036(3) 0.0021(12) -0.0057(19) -0.0081(14) C19 0.043(2) 0.0243(18) 0.0310(19) 0.0007(15) 0.0023(16) 0.0011(16) C20 0.091(7) 0.049(4) 0.034(3) -0.003(2) -0.009(4) 0.018(5) C21 0.039(3) 0.054(3) 0.027(2) 0.003(2) 0.0021(18) -0.015(2) C22 0.038(3) 0.031(3) 0.038(3) -0.0026(19) -0.002(2) -0.006(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 1.00 1.00 0.0530 -1.00 -1.00 0.00 0.1090 1.00 1.00 0.00 0.0870 0.00 0.00 -1.00 0.1310 0.00 0.00 1.00 0.1440 -1.00 1.00 0.00 0.0790 1.00 -1.00 0.00 0.1090 1.00 -1.00 1.00 0.0840 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 O1 S O2 120.35(8) . . ? O1 S N1 107.74(7) . . ? O1 S C1 105.70(8) . . ? O2 S N1 105.39(7) . . ? O2 S C1 107.59(7) . . ? N1 S C1 109.87(8) . . ? C17 O3 C10 105.63(12) . . ? C8 N1 S 122.25(12) . . ? C17 N2 C9 107.29(13) . . ? C2 C1 S 120.39(13) . . ? C2 C1 C6 120.25(16) . . ? C6 C1 S 119.33(13) . . ? C1 C2 C3 119.43(16) . . ? C2 C3 C4 121.38(16) . . ? C3 C4 C5 118.24(16) . . ? C3 C4 C7 121.53(17) . . ? C5 C4 C7 120.22(17) . . ? C6 C5 C4 121.22(16) . . ? C5 C6 C1 119.48(16) . . ? N1 C8 C9 112.38(13) . . ? N2 C9 C8 109.80(12) . . ? N2 C9 C10 103.30(12) . . ? N2 C9 C11 109.83(12) . . ? C8 C9 C10 113.33(13) . . ? C11 C9 C8 108.16(13) . . ? C11 C9 C10 112.33(13) . . ? O3 C10 C9 103.89(12) . . ? C12 C11 C9 119.04(14) . . ? C16 C11 C9 122.11(14) . . ? C16 C11 C12 118.85(14) . . ? C13 C12 C11 120.59(15) . . ? C14 C13 C12 120.15(16) . . ? C13 C14 C15 119.94(16) . . ? C14 C15 C16 120.00(16) . . ? C11 C16 C15 120.46(15) . . ? O3 C17 C18 115.09(15) . . ? N2 C17 O3 118.18(15) . . ? N2 C17 C18 126.68(16) . . ? C19 O5 C21 117.8(3) . . ? O4 C19 O5 121.8(4) . . ? O4 C19 C20 126.5(5) . . ? O5 C19 C20 111.6(4) . . ? O5 C21 C22 112.1(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 S O1 1.4340(12) . ? S O2 1.4360(12) . ? S N1 1.6084(14) . ? S C1 1.7681(17) . ? O3 C10 1.451(2) . ? O3 C17 1.359(2) . ? N1 C8 1.458(2) . ? N2 C9 1.4756(19) . ? N2 C17 1.268(2) . ? C1 C2 1.386(2) . ? C1 C6 1.392(2) . ? C2 C3 1.387(2) . ? C3 C4 1.389(2) . ? C4 C5 1.394(3) . ? C4 C7 1.506(3) . ? C5 C6 1.384(3) . ? C8 C9 1.538(2) . ? C9 C10 1.544(2) . ? C9 C11 1.528(2) . ? C11 C12 1.388(2) . ? C11 C16 1.388(2) . ? C12 C13 1.382(2) . ? C13 C14 1.379(3) . ? C14 C15 1.379(3) . ? C15 C16 1.388(2) . ? C17 C18 1.478(2) . ? O4 C19 1.203(5) . ? O5 C19 1.317(5) . ? O5 C21 1.469(6) . ? C19 C20 1.490(8) . ? C21 C22 1.474(6) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N2 0.85(2) 2.10(2) 2.9379(19) 172(2) 2_655