#------------------------------------------------------------------------------ #$Date: 2019-11-08 03:34:34 +0200 (Fri, 08 Nov 2019) $ #$Revision: 225108 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/71/7157145.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_7157145 loop_ _publ_author_name 'Lu, Min' 'Li, Hong' 'Zou, Chuncheng' 'Li, Jianchang' 'Liu, Chengyu' 'Sun, Maolin' 'Ma, Yueyue' 'Cheng, Ruihua' 'Ye, Jinxing' _publ_section_title ; Primary amine catalyzed diastereo- and enantioselective Michael reaction of thiazolones and \a,\b-unsaturated ketones. ; _journal_issue 42 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 9305 _journal_page_last 9312 _journal_paper_doi 10.1039/c9ob02067e _journal_volume 17 _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_sum 'C27 H24 N2 O5 S' _chemical_formula_weight 488.54 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2019-08-09 deposited with the CCDC. 2019-10-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.5917(13) _cell_length_b 13.421(2) _cell_length_c 21.279(3) _cell_measurement_reflns_used 4052 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 43.932 _cell_measurement_theta_min 4.886 _cell_volume 2453.7(6) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_unetI/netI 0.0369 _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 -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 14194 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.496 _diffrn_reflns_theta_min 1.794 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.322 _exptl_crystal_description prismatic _exptl_crystal_F_000 1024 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.174 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.037 _refine_ls_abs_structure_details ; Flack x determined using 1508 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.01(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 305 _refine_ls_number_reflns 4575 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0433 _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^)+(0.0588P)^2^+0.1969P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.1114 _reflns_Friedel_coverage 0.752 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 3924 _reflns_number_total 4575 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob02067e2.cif _cod_data_source_block yelu1 _cod_depositor_comments 'Adding full bibliography for 7157145.cif.' _cod_database_code 7157145 _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 0.966 _shelx_estimated_absorpt_t_max 0.978 _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd16615 in P2(1)2(1)2(1) CELL 0.71073 8.5917 13.4214 21.2789 90.000 90.000 90.000 ZERR 4.00 0.0013 0.0021 0.0032 0.000 0.000 0.000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O S UNIT 108 96 8 20 4 OMIT -3.00 51.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 HTAB C14 O2_$2 HTAB C11 O1_$1 HTAB C11 O1_$1 HTAB C13 O2_$2 EQIV $2 x+1, y, z HTAB C11 O1_$1 EQIV $1 x+1/2, -y+1/2, -z+2 conf htab mpla s1 n1 c1 c2 c3 mpla c5 > c10 mpla c21 > c26 size 0.20 0.18 0.13 wpdb -1 HTAB C11 O1_$1 HTAB C14 O2_$2 WGHT 0.058800 0.196900 FVAR 0.19026 MOLE 1 S1 5 0.687734 0.342842 0.921036 11.00000 0.04458 0.06228 = 0.06739 0.01190 0.00778 -0.00508 N1 3 0.935253 0.422855 0.867550 11.00000 0.04500 0.04092 = 0.04247 -0.00019 0.00255 0.00071 N2 3 0.671253 0.657822 1.103506 11.00000 0.08377 0.06218 = 0.06818 -0.01300 0.01088 0.00698 O1 4 0.889259 0.245195 0.992567 11.00000 0.07397 0.05740 = 0.05816 0.01585 0.00516 -0.00548 O2 4 0.693928 0.472488 0.830979 11.00000 0.05113 0.06646 = 0.06136 0.01336 -0.00199 0.01106 O3 4 1.317608 0.544292 1.025058 11.00000 0.10025 0.12677 = 0.06387 0.00060 -0.02196 -0.03483 O4 4 0.623304 0.733944 1.080178 11.00000 0.12005 0.08529 = 0.09446 0.00183 0.01886 0.04311 O5 4 0.632098 0.627342 1.155110 11.00000 0.13711 0.08761 = 0.08148 -0.01085 0.04567 0.01539 C1 1 0.872625 0.304269 0.950467 11.00000 0.05733 0.04009 = 0.04552 -0.00115 0.00412 0.00011 C2 1 1.002970 0.356998 0.914129 11.00000 0.04552 0.04537 = 0.04411 0.00291 0.00253 0.00363 C3 1 0.789356 0.420841 0.867233 11.00000 0.04608 0.04118 = 0.04435 -0.00194 0.00217 -0.00219 C4 1 0.768131 0.539431 0.785125 11.00000 0.07953 0.09333 = 0.06317 0.03067 0.02243 0.03150 AFIX 23 H4A 2 0.757814 0.512017 0.743153 11.00000 -1.20000 H4B 2 0.878125 0.545880 0.794561 11.00000 -1.20000 AFIX 66 C5 1 0.692475 0.638312 0.788079 11.00000 0.04814 0.06594 = 0.05169 0.01229 0.00674 0.00013 C6 1 0.734977 0.705187 0.834912 11.00000 0.09224 0.10460 = 0.07200 0.00415 -0.00377 -0.02644 AFIX 43 H6 2 0.810285 0.687551 0.864269 11.00000 -1.20000 AFIX 65 C7 1 0.664923 0.798422 0.837867 11.00000 0.17143 0.07248 = 0.13496 -0.02143 0.05326 -0.04993 AFIX 43 H7 2 0.693360 0.843166 0.869202 11.00000 -1.20000 AFIX 65 C8 1 0.552366 0.824782 0.793990 11.00000 0.15337 0.06693 = 0.18132 0.01887 0.06891 0.01661 AFIX 43 H8 2 0.505496 0.887163 0.795968 11.00000 -1.20000 AFIX 65 C9 1 0.509863 0.757908 0.747156 11.00000 0.08651 0.10966 = 0.14503 0.04411 -0.00068 0.03417 AFIX 43 H9 2 0.434556 0.775545 0.717800 11.00000 -1.20000 AFIX 65 C10 1 0.579917 0.664672 0.744200 11.00000 0.07047 0.09024 = 0.07549 0.00877 -0.00811 0.01418 AFIX 43 H10 2 0.551479 0.619929 0.712866 11.00000 -1.20000 AFIX 0 C11 1 1.101581 0.418829 0.962120 11.00000 0.04897 0.04649 = 0.04485 0.00117 -0.00288 0.00070 AFIX 13 H11 2 1.150462 0.371667 0.991217 11.00000 -1.20000 AFIX 0 C12 1 1.231918 0.475260 0.928475 11.00000 0.04589 0.06671 = 0.05695 -0.00362 0.00052 -0.00276 AFIX 23 H12A 2 1.299650 0.426983 0.908403 11.00000 -1.20000 H12B 2 1.185725 0.515523 0.895533 11.00000 -1.20000 AFIX 0 C13 1 1.330025 0.541863 0.969179 11.00000 0.04537 0.06104 = 0.06985 -0.00584 -0.00688 0.00080 C14 1 1.446096 0.604103 0.935594 11.00000 0.05980 0.08418 = 0.10376 -0.01502 0.00945 -0.01759 AFIX 137 H14A 2 1.500586 0.645112 0.965297 11.00000 -1.50000 H14B 2 1.393819 0.645673 0.905554 11.00000 -1.50000 H14C 2 1.518955 0.561780 0.914209 11.00000 -1.50000 AFIX 0 C15 1 0.994582 0.485754 1.000418 11.00000 0.04755 0.04409 = 0.04174 0.00202 -0.00668 -0.00306 C16 1 0.939238 0.453711 1.058601 11.00000 0.07679 0.04726 = 0.04401 0.00537 -0.00142 0.00698 AFIX 43 H15 2 0.974974 0.393830 1.075198 11.00000 -1.20000 AFIX 0 C17 1 0.832951 0.508980 1.091817 11.00000 0.08150 0.05757 = 0.03982 0.00110 0.00974 -0.00078 AFIX 43 H16 2 0.794788 0.486117 1.130090 11.00000 -1.20000 AFIX 0 C18 1 0.784061 0.597993 1.067866 11.00000 0.06006 0.05257 = 0.04989 -0.00925 0.00150 0.00159 C19 1 0.839157 0.633949 1.011135 11.00000 0.06375 0.04452 = 0.05027 0.00154 -0.00678 0.00197 AFIX 43 H18 2 0.806697 0.695424 0.995808 11.00000 -1.20000 AFIX 0 C20 1 0.943062 0.576500 0.978021 11.00000 0.05507 0.04676 = 0.04307 0.00320 -0.00221 -0.00598 AFIX 43 H19 2 0.979663 0.599347 0.939497 11.00000 -1.20000 AFIX 0 C21 1 1.102457 0.275710 0.881397 11.00000 0.04926 0.05207 = 0.05830 0.00021 0.00469 0.00431 AFIX 23 H21A 2 1.179348 0.307727 0.854819 11.00000 -1.20000 H21B 2 1.157690 0.237809 0.913164 11.00000 -1.20000 AFIX 0 C22 1 1.006171 0.204909 0.841816 11.00000 0.04958 0.04473 = 0.05569 -0.00460 0.00797 0.00941 C23 1 0.963032 0.228981 0.781132 11.00000 0.07367 0.04998 = 0.05165 -0.00056 0.01070 0.00662 AFIX 43 H23 2 0.994927 0.289286 0.763884 11.00000 -1.20000 AFIX 0 C24 1 0.873245 0.164733 0.745770 11.00000 0.08830 0.06773 = 0.06160 -0.00767 -0.00760 0.00827 AFIX 43 H24 2 0.844029 0.182140 0.705144 11.00000 -1.20000 AFIX 0 C25 1 0.827274 0.075389 0.770568 11.00000 0.07709 0.07505 = 0.08433 -0.02329 -0.00578 -0.00602 AFIX 43 H25 2 0.767958 0.031466 0.746713 11.00000 -1.20000 AFIX 0 C26 1 0.869100 0.051097 0.830644 11.00000 0.08751 0.05677 = 0.09106 -0.00161 0.00935 -0.01151 AFIX 43 H26 2 0.836308 -0.009107 0.847759 11.00000 -1.20000 AFIX 0 C27 1 0.958726 0.114339 0.865955 11.00000 0.07954 0.05349 = 0.06342 0.00492 0.00359 0.00234 AFIX 43 H27 2 0.987809 0.096145 0.906459 11.00000 -1.20000 AFIX 0 HKLF 4 REM cd16615 in P2(1)2(1)2(1) REM R1 = 0.0433 for 3924 Fo > 4sig(Fo) and 0.0522 for all 4575 data REM 305 parameters refined using 0 restraints END WGHT 0.0570 0.2287 REM Instructions for potential hydrogen bonds HTAB C11 O1_$1 HTAB C14 O2_$2 REM Highest difference peak 0.174, deepest hole -0.160, 1-sigma level 0.037 Q1 1 0.6131 0.8141 0.7966 11.00000 0.05 0.17 Q2 1 0.7475 0.3771 0.8906 11.00000 0.05 0.16 Q3 1 0.5666 0.7851 0.7463 11.00000 0.05 0.16 Q4 1 0.7045 0.7247 0.8186 11.00000 0.05 0.15 Q5 1 0.5252 0.7626 0.7836 11.00000 0.05 0.15 Q6 1 0.5808 0.6650 0.7666 11.00000 0.05 0.15 Q7 1 1.2665 0.5806 1.0025 11.00000 0.05 0.15 Q8 1 0.6242 0.7782 0.8453 11.00000 0.05 0.15 Q9 1 0.7469 0.3276 0.8829 11.00000 0.05 0.14 Q10 1 0.8544 0.3750 0.8550 11.00000 0.05 0.14 Q11 1 0.7556 0.3065 0.8918 11.00000 0.05 0.13 Q12 1 0.7026 0.3988 0.7353 11.00000 0.05 0.13 Q13 1 0.9180 0.1949 0.8684 11.00000 0.05 0.13 Q14 1 0.6654 0.4730 0.7319 11.00000 0.05 0.13 Q15 1 1.0099 0.5912 0.9516 11.00000 0.05 0.12 Q16 1 0.8536 0.4462 0.8941 11.00000 0.05 0.12 Q17 1 0.7552 0.2851 0.9182 11.00000 0.05 0.12 Q18 1 0.9275 0.1116 0.8986 11.00000 0.05 0.12 Q19 1 1.0051 0.5399 0.9976 11.00000 0.05 0.12 Q20 1 1.0452 0.1345 0.8498 11.00000 0.05 0.11 ; _shelx_res_checksum 23666 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 _atom_site_refinement_flags_adp S1 S 0.68773(9) 0.34284(7) 0.92104(4) 0.0581(3) Uani 1 1 d . . N1 N 0.9353(3) 0.42286(18) 0.86755(11) 0.0428(6) Uani 1 1 d . . N2 N 0.6713(4) 0.6578(3) 1.10351(16) 0.0714(9) Uani 1 1 d . . O1 O 0.8893(3) 0.24520(19) 0.99257(11) 0.0632(6) Uani 1 1 d . . O2 O 0.6939(3) 0.47249(18) 0.83098(11) 0.0597(6) Uani 1 1 d . . O3 O 1.3176(4) 0.5443(3) 1.02506(14) 0.0970(11) Uani 1 1 d . . O4 O 0.6233(4) 0.7339(2) 1.08018(15) 0.0999(11) Uani 1 1 d . . O5 O 0.6321(5) 0.6273(2) 1.15511(15) 0.1021(11) Uani 1 1 d . . C1 C 0.8726(4) 0.3043(2) 0.95047(14) 0.0476(7) Uani 1 1 d . . C2 C 1.0030(3) 0.3570(2) 0.91413(14) 0.0450(7) Uani 1 1 d . . C3 C 0.7894(4) 0.4208(2) 0.86723(14) 0.0439(7) Uani 1 1 d . . C4 C 0.7681(5) 0.5394(3) 0.78513(18) 0.0787(13) Uani 1 1 d . . H4A H 0.7578 0.5120 0.7432 0.094 Uiso 1 1 calc R U H4B H 0.8781 0.5459 0.7946 0.094 Uiso 1 1 calc R U C5 C 0.6925(3) 0.63831(18) 0.78808(12) 0.0553(8) Uani 1 1 d G . C6 C 0.7350(4) 0.7052(3) 0.83491(12) 0.0896(14) Uani 1 1 d G . H6 H 0.8103 0.6876 0.8643 0.108 Uiso 1 1 calc R U C7 C 0.6649(5) 0.7984(2) 0.83787(18) 0.126(2) Uani 1 1 d G . H7 H 0.6934 0.8432 0.8692 0.152 Uiso 1 1 calc R U C8 C 0.5524(5) 0.82478(19) 0.7940(2) 0.134(3) Uani 1 1 d G . H8 H 0.5055 0.8872 0.7960 0.161 Uiso 1 1 calc R U C9 C 0.5099(4) 0.7579(3) 0.74716(19) 0.1137(19) Uani 1 1 d G . H9 H 0.4346 0.7755 0.7178 0.136 Uiso 1 1 calc R U C10 C 0.5799(3) 0.6647(2) 0.74420(12) 0.0787(12) Uani 1 1 d G . H10 H 0.5515 0.6199 0.7129 0.094 Uiso 1 1 calc R U C11 C 1.1016(4) 0.4188(2) 0.96212(14) 0.0468(7) Uani 1 1 d . . H11 H 1.1505 0.3717 0.9912 0.056 Uiso 1 1 calc R U C12 C 1.2319(4) 0.4753(3) 0.92848(16) 0.0565(8) Uani 1 1 d . . H12A H 1.2996 0.4270 0.9084 0.068 Uiso 1 1 calc R U H12B H 1.1857 0.5155 0.8955 0.068 Uiso 1 1 calc R U C13 C 1.3300(4) 0.5419(3) 0.96918(18) 0.0588(9) Uani 1 1 d . . C14 C 1.4461(5) 0.6041(3) 0.9356(2) 0.0826(12) Uani 1 1 d . . H14A H 1.5006 0.6451 0.9653 0.124 Uiso 1 1 calc R U H14B H 1.3938 0.6457 0.9056 0.124 Uiso 1 1 calc R U H14C H 1.5190 0.5618 0.9142 0.124 Uiso 1 1 calc R U C15 C 0.9946(4) 0.4858(2) 1.00042(13) 0.0445(7) Uani 1 1 d . . C16 C 0.9392(4) 0.4537(3) 1.05860(15) 0.0560(9) Uani 1 1 d . . H15 H 0.9750 0.3938 1.0752 0.067 Uiso 1 1 calc R U C17 C 0.8330(4) 0.5090(3) 1.09182(14) 0.0596(9) Uani 1 1 d . . H16 H 0.7948 0.4861 1.1301 0.072 Uiso 1 1 calc R U C18 C 0.7841(4) 0.5980(3) 1.06787(15) 0.0542(8) Uani 1 1 d . . C19 C 0.8392(4) 0.6339(2) 1.01113(14) 0.0529(8) Uani 1 1 d . . H18 H 0.8067 0.6954 0.9958 0.063 Uiso 1 1 calc R U C20 C 0.9431(4) 0.5765(2) 0.97802(15) 0.0483(8) Uani 1 1 d . . H19 H 0.9797 0.5993 0.9395 0.058 Uiso 1 1 calc R U C21 C 1.1025(4) 0.2757(2) 0.88140(16) 0.0532(8) Uani 1 1 d . . H21A H 1.1793 0.3077 0.8548 0.064 Uiso 1 1 calc R U H21B H 1.1577 0.2378 0.9132 0.064 Uiso 1 1 calc R U C22 C 1.0062(4) 0.2049(2) 0.84182(15) 0.0500(8) Uani 1 1 d . . C23 C 0.9630(4) 0.2290(3) 0.78113(16) 0.0584(9) Uani 1 1 d . . H23 H 0.9949 0.2893 0.7639 0.070 Uiso 1 1 calc R U C24 C 0.8732(5) 0.1647(3) 0.74577(19) 0.0725(10) Uani 1 1 d . . H24 H 0.8440 0.1821 0.7051 0.087 Uiso 1 1 calc R U C25 C 0.8273(5) 0.0754(3) 0.7706(2) 0.0788(12) Uani 1 1 d . . H25 H 0.7680 0.0315 0.7467 0.095 Uiso 1 1 calc R U C26 C 0.8691(5) 0.0511(3) 0.8306(2) 0.0784(12) Uani 1 1 d . . H26 H 0.8363 -0.0091 0.8478 0.094 Uiso 1 1 calc R U C27 C 0.9587(5) 0.1143(3) 0.86596(18) 0.0655(10) Uani 1 1 d . . H27 H 0.9878 0.0961 0.9065 0.079 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 S1 0.0446(4) 0.0623(6) 0.0674(5) 0.0119(4) 0.0078(4) -0.0051(4) N1 0.0450(14) 0.0409(14) 0.0425(13) -0.0002(11) 0.0025(11) 0.0007(11) N2 0.084(2) 0.062(2) 0.068(2) -0.0130(17) 0.0109(17) 0.007(2) O1 0.0740(16) 0.0574(14) 0.0582(14) 0.0159(12) 0.0052(12) -0.0055(12) O2 0.0511(12) 0.0665(15) 0.0614(13) 0.0134(12) -0.0020(11) 0.0111(11) O3 0.100(2) 0.127(3) 0.0639(17) 0.0006(17) -0.0220(17) -0.035(2) O4 0.120(3) 0.085(2) 0.094(2) 0.0018(19) 0.0189(19) 0.043(2) O5 0.137(3) 0.088(2) 0.081(2) -0.0108(17) 0.046(2) 0.015(2) C1 0.0573(19) 0.0401(17) 0.0455(17) -0.0011(14) 0.0041(14) 0.0001(14) C2 0.0455(15) 0.0454(18) 0.0441(16) 0.0029(14) 0.0025(13) 0.0036(14) C3 0.0461(18) 0.0412(17) 0.0444(16) -0.0019(13) 0.0022(13) -0.0022(13) C4 0.080(3) 0.093(3) 0.063(2) 0.031(2) 0.0224(19) 0.031(2) C5 0.0481(17) 0.066(2) 0.0517(18) 0.0123(16) 0.0067(15) 0.0001(17) C6 0.092(3) 0.105(4) 0.072(3) 0.004(3) -0.004(2) -0.026(3) C7 0.171(7) 0.072(4) 0.135(5) -0.021(4) 0.053(5) -0.050(4) C8 0.153(6) 0.067(4) 0.181(7) 0.019(4) 0.069(5) 0.017(4) C9 0.087(3) 0.110(5) 0.145(5) 0.044(4) -0.001(3) 0.034(3) C10 0.070(2) 0.090(3) 0.075(3) 0.009(2) -0.008(2) 0.014(2) C11 0.0490(17) 0.0465(18) 0.0449(16) 0.0012(14) -0.0029(13) 0.0007(15) C12 0.0459(17) 0.067(2) 0.0569(19) -0.0036(17) 0.0005(15) -0.0028(16) C13 0.0454(18) 0.061(2) 0.070(2) -0.0058(18) -0.0069(16) 0.0008(17) C14 0.060(2) 0.084(3) 0.104(3) -0.015(3) 0.009(2) -0.018(2) C15 0.0475(16) 0.0441(18) 0.0417(16) 0.0020(14) -0.0067(13) -0.0031(14) C16 0.077(2) 0.0473(19) 0.0440(17) 0.0054(15) -0.0014(16) 0.0070(17) C17 0.082(2) 0.058(2) 0.0398(16) 0.0011(15) 0.0097(17) -0.0008(19) C18 0.060(2) 0.053(2) 0.0499(18) -0.0093(16) 0.0015(15) 0.0016(16) C19 0.064(2) 0.0445(18) 0.0503(18) 0.0015(14) -0.0068(15) 0.0020(16) C20 0.0551(18) 0.0468(19) 0.0431(16) 0.0032(14) -0.0022(14) -0.0060(15) C21 0.0493(18) 0.052(2) 0.0583(19) 0.0002(16) 0.0047(15) 0.0043(16) C22 0.0496(17) 0.0447(18) 0.0557(19) -0.0046(15) 0.0080(15) 0.0094(14) C23 0.074(2) 0.050(2) 0.0517(18) -0.0006(16) 0.0107(16) 0.0066(17) C24 0.088(3) 0.068(3) 0.062(2) -0.008(2) -0.008(2) 0.008(2) C25 0.077(3) 0.075(3) 0.084(3) -0.023(2) -0.006(2) -0.006(2) C26 0.088(3) 0.057(2) 0.091(3) -0.002(2) 0.009(2) -0.012(2) C27 0.080(3) 0.053(2) 0.063(2) 0.0049(18) 0.0036(19) 0.0023(19) 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 C3 S1 C1 87.69(15) C3 N1 C2 113.1(3) O4 N2 O5 124.0(3) O4 N2 C18 118.4(3) O5 N2 C18 117.6(3) C3 O2 C4 116.0(3) O1 C1 C2 126.3(3) O1 C1 S1 123.9(3) C2 C1 S1 109.8(2) N1 C2 C1 109.4(2) N1 C2 C21 110.1(2) C1 C2 C21 107.7(3) N1 C2 C11 109.9(2) C1 C2 C11 108.1(2) C21 C2 C11 111.6(2) N1 C3 O2 127.7(3) N1 C3 S1 120.0(2) O2 C3 S1 112.3(2) O2 C4 C5 109.2(3) O2 C4 H4A 109.8 C5 C4 H4A 109.8 O2 C4 H4B 109.8 C5 C4 H4B 109.8 H4A C4 H4B 108.3 C6 C5 C10 120.0 C6 C5 C4 119.6(3) C10 C5 C4 120.4(3) C5 C6 C7 120.0 C5 C6 H6 120.0 C7 C6 H6 120.0 C8 C7 C6 120.0 C8 C7 H7 120.0 C6 C7 H7 120.0 C7 C8 C9 120.0 C7 C8 H8 120.0 C9 C8 H8 120.0 C10 C9 C8 120.0 C10 C9 H9 120.0 C8 C9 H9 120.0 C9 C10 C5 120.0 C9 C10 H10 120.0 C5 C10 H10 120.0 C15 C11 C12 113.6(3) C15 C11 C2 109.6(2) C12 C11 C2 110.7(2) C15 C11 H11 107.6 C12 C11 H11 107.6 C2 C11 H11 107.6 C13 C12 C11 115.8(3) C13 C12 H12A 108.3 C11 C12 H12A 108.3 C13 C12 H12B 108.3 C11 C12 H12B 108.3 H12A C12 H12B 107.4 O3 C13 C14 121.6(4) O3 C13 C12 122.7(4) C14 C13 C12 115.7(3) C13 C14 H14A 109.5 C13 C14 H14B 109.5 H14A C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C20 C15 C16 118.0(3) C20 C15 C11 122.0(3) C16 C15 C11 120.0(3) C17 C16 C15 121.2(3) C17 C16 H15 119.4 C15 C16 H15 119.4 C18 C17 C16 119.0(3) C18 C17 H16 120.5 C16 C17 H16 120.5 C17 C18 C19 121.7(3) C17 C18 N2 119.2(3) C19 C18 N2 119.0(3) C20 C19 C18 118.3(3) C20 C19 H18 120.9 C18 C19 H18 120.9 C19 C20 C15 121.8(3) C19 C20 H19 119.1 C15 C20 H19 119.1 C22 C21 C2 112.9(3) C22 C21 H21A 109.0 C2 C21 H21A 109.0 C22 C21 H21B 109.0 C2 C21 H21B 109.0 H21A C21 H21B 107.8 C27 C22 C23 118.3(3) C27 C22 C21 120.4(3) C23 C22 C21 121.3(3) C24 C23 C22 120.9(4) C24 C23 H23 119.6 C22 C23 H23 119.6 C25 C24 C23 119.9(4) C25 C24 H24 120.0 C23 C24 H24 120.0 C26 C25 C24 119.6(4) C26 C25 H25 120.2 C24 C25 H25 120.2 C25 C26 C27 120.8(4) C25 C26 H26 119.6 C27 C26 H26 119.6 C26 C27 C22 120.5(4) C26 C27 H27 119.8 C22 C27 H27 119.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C3 1.780(3) S1 C1 1.784(3) N1 C3 1.254(4) N1 C2 1.450(4) N2 O4 1.208(4) N2 O5 1.219(4) N2 C18 1.469(4) O1 C1 1.205(4) O2 C3 1.322(4) O2 C4 1.472(4) O3 C13 1.194(4) C1 C2 1.534(4) C2 C21 1.551(4) C2 C11 1.565(4) C4 C5 1.479(4) C4 H4A 0.9700 C4 H4B 0.9700 C5 C6 1.3900 C5 C10 1.3900 C6 C7 1.3900 C6 H6 0.9300 C7 C8 1.3900 C7 H7 0.9300 C8 C9 1.3900 C8 H8 0.9300 C9 C10 1.3900 C9 H9 0.9300 C10 H10 0.9300 C11 C15 1.522(4) C11 C12 1.530(5) C11 H11 0.9800 C12 C13 1.503(5) C12 H12A 0.9700 C12 H12B 0.9700 C13 C14 1.484(5) C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C15 C20 1.381(4) C15 C16 1.394(4) C16 C17 1.372(5) C16 H15 0.9300 C17 C18 1.365(5) C17 H16 0.9300 C18 C19 1.384(5) C19 C20 1.374(4) C19 H18 0.9300 C20 H19 0.9300 C21 C22 1.515(5) C21 H21A 0.9700 C21 H21B 0.9700 C22 C27 1.381(5) C22 C23 1.382(5) C23 C24 1.380(5) C23 H23 0.9300 C24 C25 1.368(6) C24 H24 0.9300 C25 C26 1.367(6) C25 H25 0.9300 C26 C27 1.370(6) C26 H26 0.9300 C27 H27 0.9300 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 C14 H14C O2 0.96 2.61 3.551(5) 165.3 1_655 C11 H11 O1 0.98 2.61 3.447(4) 144.1 4_557 C11 H11 O1 0.98 2.61 3.447(4) 144.1 4_557 C11 H11 O1 0.98 2.61 3.447(4) 144.1 4_557 C11 H11 O1 0.98 2.61 3.447(4) 144.1 4_557 C14 H14C O2 0.96 2.61 3.551(5) 165.3 1_655 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 C3 S1 C1 O1 179.8(3) C3 S1 C1 C2 -0.4(2) C3 N1 C2 C1 -0.7(4) C3 N1 C2 C21 117.5(3) C3 N1 C2 C11 -119.3(3) O1 C1 C2 N1 -179.5(3) S1 C1 C2 N1 0.7(3) O1 C1 C2 C21 60.8(4) S1 C1 C2 C21 -119.0(2) O1 C1 C2 C11 -59.9(4) S1 C1 C2 C11 120.3(2) C2 N1 C3 O2 179.4(3) C2 N1 C3 S1 0.4(4) C4 O2 C3 N1 0.7(5) C4 O2 C3 S1 179.8(2) C1 S1 C3 N1 0.0(3) C1 S1 C3 O2 -179.1(2) C3 O2 C4 C5 -132.5(3) O2 C4 C5 C6 80.9(3) O2 C4 C5 C10 -99.4(3) C10 C5 C6 C7 0.0 C4 C5 C6 C7 179.7(3) C5 C6 C7 C8 0.0 C6 C7 C8 C9 0.0 C7 C8 C9 C10 0.0 C8 C9 C10 C5 0.0 C6 C5 C10 C9 0.0 C4 C5 C10 C9 -179.7(3) N1 C2 C11 C15 66.7(3) C1 C2 C11 C15 -52.7(3) C21 C2 C11 C15 -170.9(2) N1 C2 C11 C12 -59.4(3) C1 C2 C11 C12 -178.8(3) C21 C2 C11 C12 63.0(3) C15 C11 C12 C13 53.1(4) C2 C11 C12 C13 176.9(3) C11 C12 C13 O3 6.7(5) C11 C12 C13 C14 -174.2(3) C12 C11 C15 C20 42.2(4) C2 C11 C15 C20 -82.2(4) C12 C11 C15 C16 -141.1(3) C2 C11 C15 C16 94.5(3) C20 C15 C16 C17 2.0(5) C11 C15 C16 C17 -174.8(3) C15 C16 C17 C18 -1.6(5) C16 C17 C18 C19 -0.2(5) C16 C17 C18 N2 -179.5(3) O4 N2 C18 C17 -176.3(4) O5 N2 C18 C17 3.8(5) O4 N2 C18 C19 4.3(5) O5 N2 C18 C19 -175.5(4) C17 C18 C19 C20 1.5(5) N2 C18 C19 C20 -179.2(3) C18 C19 C20 C15 -1.0(5) C16 C15 C20 C19 -0.7(5) C11 C15 C20 C19 176.0(3) N1 C2 C21 C22 -66.1(3) C1 C2 C21 C22 53.1(3) C11 C2 C21 C22 171.6(3) C2 C21 C22 C27 -96.7(4) C2 C21 C22 C23 83.1(4) C27 C22 C23 C24 0.8(5) C21 C22 C23 C24 -179.0(3) C22 C23 C24 C25 -0.7(6) C23 C24 C25 C26 0.9(6) C24 C25 C26 C27 -1.1(7) C25 C26 C27 C22 1.2(6) C23 C22 C27 C26 -1.0(5) C21 C22 C27 C26 178.7(3)