#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:30:01 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252920 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157491.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_7157491 loop_ _publ_author_name 'Tota, Arianna' 'Carlucci, Claudia' 'Pisano, Luisa' 'Cutolo, Giuliano' 'Clarkson, Guy J.' 'Romanazzi, Giuseppe' 'Degennaro, Leonardo' 'Bull, James A.' 'Rollin, Patrick' 'Luisi, Renzo' _publ_section_title ; Synthesis of glycosyl sulfoximines by a highly chemo- and stereoselective NH- and O-transfer to thioglycosides. ; _journal_issue 20 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3893 _journal_page_last 3897 _journal_paper_doi 10.1039/d0ob00647e _journal_volume 18 _journal_year 2020 _chemical_absolute_configuration rmad _chemical_formula_moiety '2(C20 H31 N O10 S), C5 H12' _chemical_formula_sum 'C45 H74 N2 O20 S2' _chemical_formula_weight 1027.18 _space_group_crystal_system tetragonal _space_group_IT_number 96 _space_group_name_Hall 'P 4nw 2abw' _space_group_name_H-M_alt 'P 43 21 2' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-06-23 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-01-24 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.74142(5) _cell_length_b 9.74142(5) _cell_length_c 55.7588(4) _cell_measurement_reflns_used 25529 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 73.6410 _cell_measurement_theta_min 3.1180 _cell_volume 5291.25(5) _computing_cell_refinement 'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.6093 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -74.00 34.00 1.00 1.00 -- -41.82 77.00 -90.00 108 2 \w -66.00 33.00 1.00 1.00 -- -41.82 37.00-180.00 99 3 \w 103.00 178.00 1.00 4.00 -- 107.00 77.00 120.00 75 4 \w 103.00 178.00 1.00 4.00 -- 107.00 77.00 60.00 75 5 \w 81.00 178.00 1.00 4.00 -- 107.00 45.00-150.00 97 6 \w 103.00 178.00 1.00 4.00 -- 107.00 77.00 0.00 75 7 \w 81.00 178.00 1.00 4.00 -- 107.00 45.00-120.00 97 8 \w 81.00 178.00 1.00 4.00 -- 107.00 45.00 -30.00 97 9 \w 35.00 136.00 1.00 4.00 -- 107.00 -61.00 -90.00 101 10 \w -114.00 -14.00 1.00 1.00 -- -41.82 -57.00-120.00 100 11 \w -114.00 -14.00 1.00 1.00 -- -41.82 -57.00 30.00 100 12 \w -114.00 -14.00 1.00 1.00 -- -41.82 -57.00 150.00 100 13 \w 81.00 178.00 1.00 4.00 -- 107.00 45.00 90.00 97 14 \w 24.00 107.00 1.00 4.00 -- 107.00 -94.00-150.00 83 15 \w 34.00 112.00 1.00 4.00 -- 107.00-125.00 120.00 78 16 \w 78.00 178.00 1.00 4.00 -- 107.00 61.00 -90.00 100 17 \w 78.00 178.00 1.00 4.00 -- 107.00 61.00 150.00 100 18 \w 34.00 112.00 1.00 4.00 -- 107.00-125.00-180.00 78 19 \w -114.00 -14.00 1.00 1.00 -- -41.82 -57.00 90.00 100 20 \w -114.00 -14.00 1.00 1.00 -- -41.82 -57.00 -30.00 100 21 \w 61.00 131.00 1.00 1.00 -- 41.82 178.00 150.00 70 22 \w 78.00 178.00 1.00 4.00 -- 107.00 61.00 120.00 100 23 \w 78.00 178.00 1.00 4.00 -- 107.00 61.00 0.00 100 24 \w 24.00 107.00 1.00 4.00 -- 107.00 -94.00 -90.00 83 25 \w 78.00 162.00 1.00 4.00 -- 107.00 61.00 -60.00 84 26 \w 78.00 178.00 1.00 4.00 -- 107.00 61.00 30.00 100 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0031424000 _diffrn_orient_matrix_UB_12 0.1543298000 _diffrn_orient_matrix_UB_13 -0.0059787000 _diffrn_orient_matrix_UB_21 -0.0220009000 _diffrn_orient_matrix_UB_22 -0.0343954000 _diffrn_orient_matrix_UB_23 -0.0266963000 _diffrn_orient_matrix_UB_31 -0.1565826000 _diffrn_orient_matrix_UB_32 0.0017829000 _diffrn_orient_matrix_UB_33 0.0038777000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_unetI/netI 0.0185 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 68 _diffrn_reflns_limit_l_min -69 _diffrn_reflns_number 78929 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.704 _diffrn_reflns_theta_min 3.170 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.547 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.01863 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.289 _exptl_crystal_description block _exptl_crystal_F_000 2200 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.639 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.057 _refine_ls_abs_structure_details ; Flack x determined using 1983 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). Flack x: 0.007(5) Shelx 2018 Hooft y: -0.002(5) Olex2 the molecule contains known chiral centres that are not affected by the synthetic steps ; _refine_ls_abs_structure_Flack 0.007(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 320 _refine_ls_number_reflns 5339 _refine_ls_number_restraints 9 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0464 _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^)+(0.0544P)^2^+5.3337P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1189 _refine_ls_wR_factor_ref 0.1193 _reflns_Friedel_coverage 0.648 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 5274 _reflns_number_total 5339 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00647e2.cif _cod_data_source_block rl3 _cod_depositor_comments 'Adding full bibliography for 7157491.cif.' _cod_original_cell_volume 5291.24(7) _cod_database_code 7157491 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C20 H20 N2 O2' _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_max 0.886 _shelx_estimated_absorpt_t_min 0.654 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 71.98 _olex2_refinement_description ; The determination of the oxygen and nitrogen of the sulfoximine was decided by taking into account the thermal ellipsoids of the two atoms, bond lengths (S=O shorter than S=N as confirmed from related structures in the CCDC) and the hydrogen was located in a difference map confirming the identity of the nitrogen (see below). The hydrogen (H7) on the nitrogen was located in a difference map and its position allowed to refine freely but given thermal ellipsoids 1.2 times the equivalent isotropic displacement parameter of N7 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Rigid body (RIGU) restrains C100, C101, C102 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001 3. Others Fixed Sof: H10G(0.5) H10F(0.5) 4.a Ternary CH refined with riding coordinates: C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12) 4.b Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C13(H13A, H13B), C101(H10D,H10E), C102(H10G,H10F) 4.c Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B, H22C), C100(H10A,H10B,H10C) ; _shelx_res_file ; TITL rl3_a.res in P4(3)2(1)2 rl3.res created by SHELXL-2018/3 at 09:00:41 on 23-Jun-2019 REM Old TITL rl3 in P4(1)2(1)2 REM SHELXT solution in P4(3)2(1)2: R1 0.101, Rweak 0.026, Alpha 0.004 REM 1.287 for 54 systematic absences, Orientation as input REM Flack x = 0.108 ( 0.006 ) from 1884 Parsons' quotients REM Formula found by SHELXT: C45 N2 O20 Cl2 CELL 1.54184 9.741416 9.741416 55.758802 90 90 90 ZERR 4 0.000053 0.000053 0.000375 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-Y,0.5+X,0.75+Z SYMM 0.5+Y,0.5-X,0.25+Z SYMM 0.5-X,0.5+Y,0.75-Z SYMM 0.5+X,0.5-Y,0.25-Z SYMM +Y,+X,-Z SYMM -Y,-X,0.5-Z SFAC C H N O S UNIT 180 296 8 80 8 EQIV $1 1.5-X,-0.5+Y,0.75-Z RIGU 0.0001 0.0001 C100 C101 C102 L.S. 4 PLAN 20 SIZE 0.08 0.2 0.3 TEMP -123(2) HTAB N7 O21 HTAB N7 O15_$1 BOND $H HTAB list 4 fmap 2 acta REM REM REM WGHT 0.054400 5.333700 FVAR 2.63266 C1 1 0.686360 0.625153 0.421409 11.00000 0.02579 0.02441 = 0.03117 -0.00418 -0.00164 -0.00001 AFIX 23 H1A 2 0.623365 0.642407 0.407807 11.00000 -1.20000 H1B 2 0.750277 0.703853 0.422635 11.00000 -1.20000 AFIX 0 C2 1 0.603445 0.612399 0.444684 11.00000 0.02903 0.04748 = 0.03078 -0.00872 0.00329 0.00112 AFIX 23 H2A 2 0.555292 0.699952 0.447925 11.00000 -1.20000 H2B 2 0.533430 0.539477 0.442864 11.00000 -1.20000 AFIX 0 C3 1 0.697697 0.577780 0.465760 11.00000 0.04910 0.06783 = 0.02583 -0.00877 -0.00094 0.00859 AFIX 23 H3A 2 0.763420 0.653885 0.468332 11.00000 -1.20000 H3B 2 0.642248 0.567165 0.480524 11.00000 -1.20000 AFIX 0 C4 1 0.775762 0.446327 0.460903 11.00000 0.05091 0.05728 = 0.02657 0.00754 -0.00361 0.00405 AFIX 23 H4A 2 0.710065 0.369403 0.459200 11.00000 -1.20000 H4B 2 0.836687 0.425885 0.474658 11.00000 -1.20000 AFIX 0 C5 1 0.861911 0.458501 0.438005 11.00000 0.03269 0.03022 = 0.02878 0.00175 -0.00568 0.00276 AFIX 23 H5A 2 0.909919 0.370746 0.434867 11.00000 -1.20000 H5B 2 0.931878 0.531324 0.439995 11.00000 -1.20000 AFIX 0 C6 1 0.767587 0.493547 0.416836 11.00000 0.02265 0.01995 = 0.02447 -0.00002 -0.00047 -0.00296 AFIX 13 H6 2 0.701824 0.416086 0.414286 11.00000 -1.20000 AFIX 0 N7 3 0.930437 0.368209 0.386585 11.00000 0.02337 0.02297 = 0.03446 0.00236 0.00255 0.00324 H7 2 0.999298 0.367063 0.377267 11.00000 -1.20000 O7 4 0.962938 0.628964 0.392882 11.00000 0.02326 0.02219 = 0.04014 0.00218 -0.00432 -0.01032 S7 5 0.873402 0.511333 0.390660 11.00000 0.01707 0.01422 = 0.02599 0.00064 -0.00151 -0.00218 C8 1 0.749909 0.560810 0.367393 11.00000 0.01381 0.01523 = 0.02698 -0.00015 0.00066 -0.00256 AFIX 13 H8 2 0.725895 0.660279 0.368826 11.00000 -1.20000 AFIX 0 O8 4 0.634253 0.478694 0.371599 11.00000 0.01465 0.01885 = 0.02459 0.00187 -0.00079 -0.00248 C9 1 0.807357 0.529630 0.342561 11.00000 0.01467 0.01526 = 0.02694 0.00016 0.00065 -0.00097 AFIX 13 H9 2 0.850765 0.436605 0.342570 11.00000 -1.20000 AFIX 0 O9 4 0.908472 0.631575 0.336306 11.00000 0.01851 0.01849 = 0.03200 0.00040 0.00475 -0.00324 C10 1 0.695984 0.535619 0.323327 11.00000 0.02109 0.01774 = 0.02260 -0.00101 0.00072 0.00177 AFIX 13 H10 2 0.674648 0.633687 0.319558 11.00000 -1.20000 AFIX 0 O10 4 0.757142 0.471544 0.302650 11.00000 0.02821 0.02953 = 0.02129 -0.00053 0.00463 0.00186 C11 1 0.564878 0.462264 0.330824 11.00000 0.01853 0.01633 = 0.02571 -0.00312 -0.00382 0.00390 AFIX 13 H11 2 0.579369 0.360644 0.331024 11.00000 -1.20000 AFIX 0 O11 4 0.455796 0.498001 0.314412 11.00000 0.02265 0.02906 = 0.02794 -0.00547 -0.00634 0.00514 C12 1 0.523056 0.513201 0.355661 11.00000 0.01531 0.01739 = 0.02500 -0.00211 0.00043 0.00210 AFIX 13 H12 2 0.508601 0.614822 0.355395 11.00000 -1.20000 AFIX 0 C13 1 0.397004 0.442166 0.365005 11.00000 0.01879 0.01941 = 0.02876 -0.00220 0.00131 -0.00094 AFIX 23 H13A 2 0.318839 0.461313 0.354162 11.00000 -1.20000 H13B 2 0.412739 0.341764 0.365086 11.00000 -1.20000 AFIX 0 O14 4 0.362723 0.486945 0.388957 11.00000 0.02137 0.02159 = 0.02932 0.00157 0.00346 0.00087 C15 1 0.306086 0.612102 0.390955 11.00000 0.01550 0.02394 = 0.03710 0.00080 0.00358 0.00354 O15 4 0.289380 0.687800 0.374210 11.00000 0.04444 0.03528 = 0.04008 0.00988 0.01163 0.02230 C16 1 0.268150 0.644716 0.416303 11.00000 0.02457 0.03762 = 0.03449 -0.00524 0.00021 0.00520 AFIX 137 H16A 2 0.168414 0.655950 0.417503 11.00000 -1.50000 H16B 2 0.313518 0.729974 0.421224 11.00000 -1.50000 H16C 2 0.297651 0.569603 0.426797 11.00000 -1.50000 AFIX 0 C17 1 0.425967 0.407372 0.296689 11.00000 0.02815 0.03903 = 0.02406 -0.00623 -0.00055 -0.00022 O17 4 0.485167 0.300825 0.294124 11.00000 0.05425 0.03954 = 0.03659 -0.01435 -0.01069 0.00527 C18 1 0.312476 0.460225 0.281373 11.00000 0.03930 0.07418 = 0.03603 -0.01463 -0.01330 0.01172 AFIX 137 H18A 2 0.224328 0.443243 0.289306 11.00000 -1.50000 H18B 2 0.314036 0.413120 0.265845 11.00000 -1.50000 H18C 2 0.324363 0.559102 0.278885 11.00000 -1.50000 AFIX 0 C19 1 0.735921 0.528598 0.280934 11.00000 0.04852 0.03473 = 0.02651 0.00155 -0.00050 -0.00643 O19 4 0.658367 0.623268 0.277539 11.00000 0.08526 0.05255 = 0.03455 0.00695 -0.00414 0.02192 C20 1 0.822341 0.457600 0.262489 11.00000 0.08141 0.05589 = 0.02521 0.00082 0.01137 0.00318 AFIX 137 H20A 2 0.919535 0.467689 0.266668 11.00000 -1.50000 H20B 2 0.805572 0.498755 0.246721 11.00000 -1.50000 H20C 2 0.798443 0.359916 0.262013 11.00000 -1.50000 AFIX 0 C21 1 1.037855 0.588787 0.331644 11.00000 0.01684 0.02652 = 0.03008 -0.00200 0.00339 -0.00249 O21 4 1.074084 0.471001 0.333508 11.00000 0.02512 0.02520 = 0.07809 0.00420 0.00949 0.00630 C22 1 1.125118 0.707223 0.324073 11.00000 0.02458 0.03598 = 0.03642 0.00312 0.00673 -0.00746 AFIX 137 H22A 2 1.096079 0.738739 0.308172 11.00000 -1.50000 H22B 2 1.221419 0.678354 0.323434 11.00000 -1.50000 H22C 2 1.115100 0.782268 0.335647 11.00000 -1.50000 AFIX 0 C100 1 1.172384 0.427861 0.475982 11.00000 0.12812 0.16969 = 0.09323 0.00631 0.00969 0.07052 AFIX 137 H10A 2 1.101748 0.373207 0.484071 11.00000 -1.50000 H10B 2 1.197409 0.383669 0.460810 11.00000 -1.50000 H10C 2 1.136717 0.520115 0.472771 11.00000 -1.50000 AFIX 0 C101 1 1.291214 0.437498 0.491030 11.00000 0.14099 0.15518 = 0.11558 0.01451 -0.00716 0.06433 AFIX 23 H10D 2 1.370288 0.470857 0.481520 11.00000 -1.20000 H10E 2 1.273909 0.504062 0.504101 11.00000 -1.20000 AFIX 0 C102 1 1.319372 0.319372 0.500000 10.50000 0.15908 0.15908 = 0.15593 0.02680 -0.02680 0.05969 AFIX 23 H10G 2 1.302073 0.250818 0.487246 10.50000 -1.20000 H10F 2 1.250810 0.302057 0.512752 10.50000 -1.20000 AFIX 0 HKLF 4 REM rl3_a.res in P4(3)2(1)2 REM wR2 = 0.1193, GooF = S = 1.053, Restrained GooF = 1.053 for all data REM R1 = 0.0464 for 5274 Fo > 4sig(Fo) and 0.0469 for all 5339 data REM 320 parameters refined using 9 restraints END WGHT 0.0544 5.3338 REM Instructions for potential hydrogen bonds HTAB C1 O8 EQIV $3 -x+3/2, y+1/2, -z+3/4 HTAB C8 N7_$3 HTAB C9 N7 HTAB C12 N7_$3 HTAB C12 O15 EQIV $4 x-1, y, z HTAB C13 O21_$4 HTAB C13 O7_$1 EQIV $5 -x+1/2, y-1/2, -z+3/4 HTAB C13 O15_$5 HTAB C16 O7_$4 HTAB C16 O21_$3 EQIV $6 -y+1, -x+1, -z+1/2 HTAB C18 O19_$6 HTAB C20 O17_$6 HTAB C22 O14_$3 REM Highest difference peak 0.639, deepest hole -0.382, 1-sigma level 0.057 Q1 1 1.2481 0.4368 0.5140 11.00000 0.05 0.63 Q2 1 1.2905 0.5846 0.4857 11.00000 0.05 0.56 Q3 1 1.4126 0.4036 0.4969 11.00000 0.05 0.51 Q4 1 1.2821 0.4348 0.4849 11.00000 0.05 0.31 Q5 1 0.7646 0.6499 0.2785 11.00000 0.05 0.26 Q6 1 0.8546 0.6449 0.2850 11.00000 0.05 0.23 Q7 1 1.4128 0.5867 0.4892 11.00000 0.05 0.23 Q8 1 0.2135 0.4580 0.2492 11.00000 0.05 0.19 Q9 1 1.2343 0.5832 0.5163 11.00000 0.05 0.18 Q10 1 0.6165 0.2968 0.2917 11.00000 0.05 0.18 Q11 1 0.2446 0.6278 0.3710 11.00000 0.05 0.17 Q12 1 1.1416 0.3314 0.4812 11.00000 0.05 0.17 Q13 1 1.3381 0.6101 0.5159 11.00000 0.05 0.17 Q14 1 0.4582 0.6559 0.4828 11.00000 0.05 0.16 Q15 1 1.0392 0.3251 0.3914 11.00000 0.05 0.16 Q16 1 1.0729 0.7935 0.3211 11.00000 0.05 0.16 Q17 1 1.2938 0.6935 0.5009 11.00000 0.05 0.16 Q18 1 0.7409 0.5225 0.3347 11.00000 0.05 0.16 Q19 1 0.8708 0.3787 0.2673 11.00000 0.05 0.16 Q20 1 0.5783 0.4217 0.2500 10.50000 0.05 0.16 ; _shelx_res_checksum 97357 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 31.292 _oxdiff_exptl_absorpt_empirical_full_min 0.497 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -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 C1 C 0.6864(3) 0.6252(4) 0.42141(6) 0.0271(7) Uani 1 1 d . . . . . H1A H 0.623365 0.642407 0.407807 0.033 Uiso 1 1 calc R . . . . H1B H 0.750277 0.703853 0.422635 0.033 Uiso 1 1 calc R . . . . C2 C 0.6034(4) 0.6124(4) 0.44468(6) 0.0358(8) Uani 1 1 d . . . . . H2A H 0.555292 0.699952 0.447925 0.043 Uiso 1 1 calc R . . . . H2B H 0.533430 0.539477 0.442864 0.043 Uiso 1 1 calc R . . . . C3 C 0.6977(5) 0.5778(5) 0.46576(7) 0.0476(11) Uani 1 1 d . . . . . H3A H 0.763420 0.653885 0.468332 0.057 Uiso 1 1 calc R . . . . H3B H 0.642248 0.567165 0.480524 0.057 Uiso 1 1 calc R . . . . C4 C 0.7758(5) 0.4463(5) 0.46090(7) 0.0449(10) Uani 1 1 d . . . . . H4A H 0.710065 0.369403 0.459200 0.054 Uiso 1 1 calc R . . . . H4B H 0.836687 0.425885 0.474658 0.054 Uiso 1 1 calc R . . . . C5 C 0.8619(4) 0.4585(4) 0.43800(6) 0.0306(7) Uani 1 1 d . . . . . H5A H 0.909919 0.370746 0.434867 0.037 Uiso 1 1 calc R . . . . H5B H 0.931878 0.531324 0.439995 0.037 Uiso 1 1 calc R . . . . C6 C 0.7676(3) 0.4935(3) 0.41684(5) 0.0224(6) Uani 1 1 d . . . . . H6 H 0.701824 0.416086 0.414286 0.027 Uiso 1 1 calc R . . . . N7 N 0.9304(3) 0.3682(3) 0.38658(5) 0.0269(6) Uani 1 1 d . . . . . H7 H 0.999(5) 0.367(4) 0.3773(8) 0.032 Uiso 1 1 d R . . . . O7 O 0.9629(2) 0.6290(2) 0.39288(4) 0.0285(5) Uani 1 1 d . . . . . S7 S 0.87340(7) 0.51133(7) 0.39066(2) 0.01909(17) Uani 1 1 d . . . . . C8 C 0.7499(3) 0.5608(3) 0.36739(5) 0.0187(6) Uani 1 1 d . . . . . H8 H 0.725895 0.660279 0.368826 0.022 Uiso 1 1 calc R . . . . O8 O 0.6343(2) 0.4787(2) 0.37160(4) 0.0194(4) Uani 1 1 d . . . . . C9 C 0.8074(3) 0.5296(3) 0.34256(5) 0.0190(6) Uani 1 1 d . . . . . H9 H 0.850765 0.436605 0.342570 0.023 Uiso 1 1 calc R . . . . O9 O 0.9085(2) 0.6316(2) 0.33631(4) 0.0230(5) Uani 1 1 d . . . . . C10 C 0.6960(3) 0.5356(3) 0.32333(5) 0.0205(6) Uani 1 1 d . . . . . H10 H 0.674648 0.633687 0.319558 0.025 Uiso 1 1 calc R . . . . O10 O 0.7571(2) 0.4715(3) 0.30265(4) 0.0263(5) Uani 1 1 d . . . . . C11 C 0.5649(3) 0.4623(3) 0.33082(5) 0.0202(6) Uani 1 1 d . . . . . H11 H 0.579369 0.360644 0.331024 0.024 Uiso 1 1 calc R . . . . O11 O 0.4558(2) 0.4980(2) 0.31441(4) 0.0265(5) Uani 1 1 d . . . . . C12 C 0.5231(3) 0.5132(3) 0.35566(5) 0.0192(6) Uani 1 1 d . . . . . H12 H 0.508601 0.614822 0.355395 0.023 Uiso 1 1 calc R . . . . C13 C 0.3970(3) 0.4422(3) 0.36500(6) 0.0223(6) Uani 1 1 d . . . . . H13A H 0.318839 0.461313 0.354162 0.027 Uiso 1 1 calc R . . . . H13B H 0.412739 0.341764 0.365086 0.027 Uiso 1 1 calc R . . . . O14 O 0.3627(2) 0.4869(2) 0.38896(4) 0.0241(5) Uani 1 1 d . . . . . C15 C 0.3061(3) 0.6121(3) 0.39096(6) 0.0255(7) Uani 1 1 d . . . . . O15 O 0.2894(3) 0.6878(3) 0.37421(5) 0.0399(7) Uani 1 1 d . . . . . C16 C 0.2682(4) 0.6447(4) 0.41630(6) 0.0322(8) Uani 1 1 d . . . . . H16A H 0.168414 0.655950 0.417503 0.048 Uiso 1 1 calc GR . . . . H16B H 0.313518 0.729974 0.421224 0.048 Uiso 1 1 calc GR . . . . H16C H 0.297651 0.569603 0.426797 0.048 Uiso 1 1 calc GR . . . . C17 C 0.4260(4) 0.4074(4) 0.29669(6) 0.0304(8) Uani 1 1 d . . . . . O17 O 0.4852(3) 0.3008(3) 0.29412(5) 0.0435(7) Uani 1 1 d . . . . . C18 C 0.3125(5) 0.4602(6) 0.28137(7) 0.0498(12) Uani 1 1 d . . . . . H18A H 0.224328 0.443243 0.289306 0.075 Uiso 1 1 calc GR . . . . H18B H 0.314036 0.413120 0.265845 0.075 Uiso 1 1 calc GR . . . . H18C H 0.324363 0.559102 0.278885 0.075 Uiso 1 1 calc GR . . . . C19 C 0.7359(4) 0.5286(4) 0.28093(6) 0.0366(8) Uani 1 1 d . . . . . O19 O 0.6584(4) 0.6233(4) 0.27754(5) 0.0575(9) Uani 1 1 d . . . . . C20 C 0.8223(6) 0.4576(5) 0.26249(7) 0.0542(12) Uani 1 1 d . . . . . H20A H 0.919535 0.467689 0.266668 0.081 Uiso 1 1 calc GR . . . . H20B H 0.805572 0.498755 0.246721 0.081 Uiso 1 1 calc GR . . . . H20C H 0.798443 0.359916 0.262013 0.081 Uiso 1 1 calc GR . . . . C21 C 1.0379(3) 0.5888(3) 0.33164(6) 0.0245(7) Uani 1 1 d . . . . . O21 O 1.0741(3) 0.4710(3) 0.33351(6) 0.0428(7) Uani 1 1 d . . . . . C22 C 1.1251(4) 0.7072(4) 0.32407(6) 0.0323(8) Uani 1 1 d . . . . . H22A H 1.096079 0.738739 0.308172 0.048 Uiso 1 1 calc GR . . . . H22B H 1.221419 0.678354 0.323434 0.048 Uiso 1 1 calc GR . . . . H22C H 1.115100 0.782268 0.335647 0.048 Uiso 1 1 calc GR . . . . C100 C 1.1724(10) 0.4279(11) 0.47598(15) 0.130(3) Uani 1 1 d . U . . . H10A H 1.101748 0.373207 0.484071 0.196 Uiso 1 1 calc GR . . . . H10B H 1.197409 0.383669 0.460810 0.196 Uiso 1 1 calc GR . . . . H10C H 1.136717 0.520115 0.472771 0.196 Uiso 1 1 calc GR . . . . C101 C 1.2912(12) 0.4375(12) 0.49103(17) 0.137(3) Uani 1 1 d . U . . . H10D H 1.370288 0.470857 0.481520 0.165 Uiso 1 1 calc R . . . . H10E H 1.273909 0.504062 0.504101 0.165 Uiso 1 1 calc R . . . . C102 C 1.3194(14) 0.3194(14) 0.500000 0.158(4) Uani 1 2 d S TU P . . H10G H 1.302073 0.250818 0.487246 0.190 Uiso 0.5 1 calc R . . . . H10F H 1.250810 0.302057 0.512752 0.190 Uiso 0.5 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 C1 0.0258(16) 0.0244(16) 0.0312(16) -0.0042(13) -0.0016(13) 0.0000(14) C2 0.0290(19) 0.047(2) 0.0308(16) -0.0087(16) 0.0033(14) 0.0011(17) C3 0.049(3) 0.068(3) 0.0258(17) -0.0088(18) -0.0009(17) 0.009(2) C4 0.051(3) 0.057(3) 0.0266(17) 0.0075(17) -0.0036(17) 0.004(2) C5 0.0327(18) 0.0302(18) 0.0288(16) 0.0018(13) -0.0057(14) 0.0028(15) C6 0.0227(15) 0.0200(15) 0.0245(14) 0.0000(12) -0.0005(12) -0.0030(13) N7 0.0234(14) 0.0230(14) 0.0345(15) 0.0024(12) 0.0026(11) 0.0032(11) O7 0.0233(11) 0.0222(11) 0.0401(12) 0.0022(10) -0.0043(9) -0.0103(10) S7 0.0171(3) 0.0142(3) 0.0260(3) 0.0006(3) -0.0015(3) -0.0022(3) C8 0.0138(13) 0.0152(14) 0.0270(14) -0.0001(11) 0.0007(11) -0.0026(11) O8 0.0147(10) 0.0189(10) 0.0246(10) 0.0019(8) -0.0008(8) -0.0025(9) C9 0.0147(13) 0.0153(14) 0.0269(14) 0.0002(11) 0.0007(11) -0.0010(11) O9 0.0185(11) 0.0185(10) 0.0320(11) 0.0004(9) 0.0047(8) -0.0032(9) C10 0.0211(15) 0.0177(14) 0.0226(13) -0.0010(11) 0.0007(12) 0.0018(12) O10 0.0282(12) 0.0295(12) 0.0213(10) -0.0005(9) 0.0046(9) 0.0019(10) C11 0.0185(15) 0.0163(14) 0.0257(14) -0.0031(11) -0.0038(11) 0.0039(12) O11 0.0226(11) 0.0291(13) 0.0279(10) -0.0055(9) -0.0063(9) 0.0051(10) C12 0.0153(14) 0.0174(14) 0.0250(13) -0.0021(11) 0.0004(11) 0.0021(11) C13 0.0188(15) 0.0194(15) 0.0288(15) -0.0022(12) 0.0013(12) -0.0009(12) O14 0.0214(11) 0.0216(11) 0.0293(11) 0.0016(9) 0.0035(9) 0.0009(9) C15 0.0155(14) 0.0239(16) 0.0371(17) 0.0008(14) 0.0036(12) 0.0035(12) O15 0.0444(17) 0.0353(15) 0.0401(14) 0.0099(11) 0.0116(12) 0.0223(12) C16 0.0246(17) 0.038(2) 0.0345(17) -0.0052(15) 0.0002(13) 0.0052(15) C17 0.0281(17) 0.039(2) 0.0241(15) -0.0062(14) -0.0006(13) -0.0002(15) O17 0.0543(18) 0.0395(16) 0.0366(13) -0.0144(12) -0.0107(13) 0.0053(14) C18 0.039(2) 0.074(3) 0.036(2) -0.015(2) -0.0133(17) 0.012(2) C19 0.049(2) 0.035(2) 0.0265(16) 0.0015(15) -0.0005(15) -0.0064(18) O19 0.085(3) 0.0525(19) 0.0346(14) 0.0070(14) -0.0041(15) 0.0219(19) C20 0.081(4) 0.056(3) 0.0252(17) 0.0008(18) 0.011(2) 0.003(3) C21 0.0168(15) 0.0265(17) 0.0301(15) -0.0020(12) 0.0034(12) -0.0025(12) O21 0.0251(13) 0.0252(13) 0.078(2) 0.0042(13) 0.0095(13) 0.0063(11) C22 0.0246(17) 0.0360(19) 0.0364(17) 0.0031(15) 0.0067(15) -0.0075(15) C100 0.128(5) 0.170(7) 0.093(5) 0.006(5) 0.010(3) 0.071(5) C101 0.141(5) 0.155(4) 0.116(6) 0.015(3) -0.007(4) 0.064(5) C102 0.159(4) 0.159(4) 0.156(9) 0.027(4) -0.027(4) 0.060(5) 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' 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 H1A C1 H1B 108.1 . . ? C2 C1 H1A 109.6 . . ? C2 C1 H1B 109.6 . . ? C6 C1 H1A 109.6 . . ? C6 C1 H1B 109.6 . . ? C6 C1 C2 110.2(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C3 C2 C1 110.6(3) . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C4 C3 C2 110.5(3) . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C3 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C3 C4 C5 111.0(4) . . ? H4A C4 H4B 108.0 . . ? C5 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C4 C5 H5A 109.8 . . ? C4 C5 H5B 109.8 . . ? C4 C5 C6 109.3(3) . . ? H5A C5 H5B 108.3 . . ? C6 C5 H5A 109.8 . . ? C6 C5 H5B 109.8 . . ? C1 C6 C5 111.6(3) . . ? C1 C6 H6 109.0 . . ? C1 C6 S7 110.6(2) . . ? C5 C6 H6 109.0 . . ? C5 C6 S7 107.6(2) . . ? S7 C6 H6 109.0 . . ? S7 N7 H7 113(3) . . ? C6 S7 C8 102.94(14) . . ? N7 S7 C6 104.08(16) . . ? N7 S7 C8 112.06(15) . . ? O7 S7 C6 110.69(15) . . ? O7 S7 N7 121.34(16) . . ? O7 S7 C8 104.37(14) . . ? S7 C8 H8 110.6 . . ? O8 C8 S7 105.01(19) . . ? O8 C8 H8 110.6 . . ? O8 C8 C9 109.5(2) . . ? C9 C8 S7 110.5(2) . . ? C9 C8 H8 110.6 . . ? C8 O8 C12 111.6(2) . . ? C8 C9 H9 109.6 . . ? C8 C9 C10 111.7(2) . . ? O9 C9 C8 109.5(2) . . ? O9 C9 H9 109.6 . . ? O9 C9 C10 106.8(2) . . ? C10 C9 H9 109.6 . . ? C21 O9 C9 118.1(2) . . ? C9 C10 H10 109.4 . . ? O10 C10 C9 104.6(2) . . ? O10 C10 H10 109.4 . . ? O10 C10 C11 111.3(3) . . ? C11 C10 C9 112.7(2) . . ? C11 C10 H10 109.4 . . ? C19 O10 C10 118.5(3) . . ? C10 C11 H11 110.4 . . ? C10 C11 C12 108.7(2) . . ? O11 C11 C10 109.3(2) . . ? O11 C11 H11 110.4 . . ? O11 C11 C12 107.5(2) . . ? C12 C11 H11 110.4 . . ? C17 O11 C11 117.5(3) . . ? O8 C12 C11 106.4(2) . . ? O8 C12 H12 110.2 . . ? O8 C12 C13 107.0(2) . . ? C11 C12 H12 110.2 . . ? C13 C12 C11 112.5(3) . . ? C13 C12 H12 110.2 . . ? C12 C13 H13A 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? O14 C13 C12 111.7(2) . . ? O14 C13 H13A 109.3 . . ? O14 C13 H13B 109.3 . . ? C15 O14 C13 116.5(3) . . ? O14 C15 C16 111.9(3) . . ? O15 C15 O14 123.3(3) . . ? O15 C15 C16 124.8(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O11 C17 C18 110.6(3) . . ? O17 C17 O11 123.3(3) . . ? O17 C17 C18 126.1(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O10 C19 C20 109.9(3) . . ? O19 C19 O10 123.5(4) . . ? O19 C19 C20 126.6(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O9 C21 C22 110.3(3) . . ? O21 C21 O9 123.3(3) . . ? O21 C21 C22 126.4(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? H10A C100 H10B 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? C101 C100 H10A 109.5 . . ? C101 C100 H10B 109.5 . . ? C101 C100 H10C 109.5 . . ? C100 C101 H10D 109.7 . . ? C100 C101 H10E 109.7 . . ? H10D C101 H10E 108.2 . . ? C102 C101 C100 110.0(13) . . ? C102 C101 H10D 109.7 . . ? C102 C101 H10E 109.7 . . ? C101 C102 C101 122(2) . 7_646 ? C101 C102 H10G 106.8 7_646 . ? C101 C102 H10G 106.8 . . ? C101 C102 H10F 106.8 7_646 . ? C101 C102 H10F 106.8 . . ? H10G C102 H10F 106.6 . . ? 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 C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.534(5) . ? C1 C6 1.528(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.529(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.514(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.532(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.534(4) . ? C6 H6 1.0000 . ? C6 S7 1.795(3) . ? N7 H7 0.85(4) . ? N7 S7 1.518(3) . ? O7 S7 1.445(2) . ? S7 C8 1.834(3) . ? C8 H8 1.0000 . ? C8 O8 1.402(4) . ? C8 C9 1.524(4) . ? O8 C12 1.441(3) . ? C9 H9 1.0000 . ? C9 O9 1.442(4) . ? C9 C10 1.527(4) . ? O9 C21 1.353(4) . ? C10 H10 1.0000 . ? C10 O10 1.440(4) . ? C10 C11 1.522(4) . ? O10 C19 1.348(4) . ? C11 H11 1.0000 . ? C11 O11 1.445(4) . ? C11 C12 1.526(4) . ? O11 C17 1.357(4) . ? C12 H12 1.0000 . ? C12 C13 1.503(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 O14 1.444(4) . ? O14 C15 1.343(4) . ? C15 O15 1.201(4) . ? C15 C16 1.495(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O17 1.196(5) . ? C17 C18 1.489(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O19 1.207(5) . ? C19 C20 1.498(6) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 O21 1.205(4) . ? C21 C22 1.494(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C100 H10A 0.9800 . ? C100 H10B 0.9800 . ? C100 H10C 0.9800 . ? C100 C101 1.433(13) . ? C101 H10D 0.9900 . ? C101 H10E 0.9900 . ? C101 C102 1.284(13) . ? C102 H10G 0.9900 . ? C102 H10F 0.9900 . ? 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 _geom_hbond_publ_flag N7 H7 O15 0.85(4) 2.70(4) 3.302(4) 129(3) 5_645 yes N7 H7 O21 0.85(4) 2.74(4) 3.423(4) 139(4) . yes