#------------------------------------------------------------------------------ #$Date: 2019-10-12 05:39:25 +0300 (Sat, 12 Oct 2019) $ #$Revision: 219310 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/71/7157146.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_7157146 loop_ _publ_author_name 'Heron, Bernard Mark' 'Aiken, Stuart' 'Gabbutt, Christopher' 'Rice, Craig' 'Zonidis, Dimitrios' _publ_section_title ; Synthesis and Photochromism of Some Mono and Bis(Thienyl) Substituted Oxathiine 2,2-dioxides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB02128K _journal_year 2019 _chemical_formula_moiety 'C26 H32 N O3.50 S3' _chemical_formula_sum 'C26 H32 N O3.5 S3' _chemical_formula_weight 510.70 _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_method SHELXL-2017/1 _audit_update_record ; 2019-03-25 deposited with the CCDC. 2019-10-10 downloaded from the CCDC. ; _cell_angle_alpha 113.322(17) _cell_angle_beta 109.14(2) _cell_angle_gamma 90.79(2) _cell_formula_units_Z 2 _cell_length_a 9.869(5) _cell_length_b 11.897(5) _cell_length_c 13.181(5) _cell_measurement_reflns_used 7588 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 30.41 _cell_measurement_theta_min 2.22 _cell_volume 1324.1(10) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_unetI/netI 0.0573 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 19176 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.533 _diffrn_reflns_theta_min 2.215 _exptl_absorpt_coefficient_mu 0.309 _exptl_absorpt_correction_T_max 0.89 _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.281 _exptl_crystal_description plate _exptl_crystal_F_000 542 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.823 _refine_diff_density_min -1.120 _refine_diff_density_rms 0.080 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 331 _refine_ls_number_reflns 8011 _refine_ls_number_restraints 54 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0519 _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^)+(0.0674P)^2^+0.7738P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1309 _refine_ls_wR_factor_ref 0.1481 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5853 _reflns_number_total 8011 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob02128k2.cif _cod_data_source_block ColourChem_DZ050_0m_a _cod_original_formula_sum 'C26 H32 N O3.50 S3' _cod_database_code 7157146 _shelx_shelxl_version_number 2017/1 _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_res_file ; TITL ColourChem_DZ050_0m_a.res in P-1 ColourChem_DZ050_0m_a.res created by SHELXL-2017/1 at 16:51:34 on 25-Feb-2019 CELL 0.71073 9.8686 11.8973 13.1810 113.322 109.136 90.792 ZERR 2.000 0.0047 0.0053 0.0050 0.017 0.020 0.022 LATT 1 SFAC C H N O S UNIT 52 64 2 7 6 L.S. 10 BOND $H acta FMAP 2 PLAN 20 DELU 0.003 0.006 C16 O4 C26 C27 C25 C24 SIMU 0.003 0.006 C16 O4 C26 C27 C25 C24 TEMP -123.140 WGHT 0.067400 0.773800 FVAR 0.63018 0.46070 S1 5 0.584968 0.651861 0.950836 11.00000 0.02066 0.01929 = 0.01897 0.00671 0.00519 0.00506 S2 5 0.719764 0.117408 0.724670 11.00000 0.03708 0.02673 = 0.03480 0.01447 0.01634 0.01845 S3 5 0.452466 0.284987 0.394668 11.00000 0.03763 0.04087 = 0.02319 0.01244 0.01763 0.01551 N1 3 0.189938 0.494726 0.698513 11.00000 0.01794 0.02748 = 0.02408 0.00828 0.00458 0.00839 O1 4 0.630897 0.714208 1.076971 11.00000 0.02882 0.02722 = 0.01909 0.00524 0.00275 0.00728 O2 4 0.663558 0.687770 0.891382 11.00000 0.02349 0.02414 = 0.03055 0.01094 0.01025 0.00346 O3 4 0.588452 0.508039 0.922896 11.00000 0.02437 0.02070 = 0.01841 0.00912 0.00549 0.00777 O4 4 0.000000 1.000000 0.500000 10.50000 0.08635 0.09488 = 0.08973 0.03943 -0.00298 0.00680 C1 1 0.541768 0.424538 0.800267 11.00000 0.01860 0.01771 = 0.02019 0.00696 0.00806 0.00430 C2 1 0.434635 0.445053 0.718719 11.00000 0.01919 0.01670 = 0.01962 0.00659 0.00907 0.00446 C3 1 0.344365 0.548951 0.747910 11.00000 0.01927 0.01840 = 0.01772 0.00726 0.00676 0.00637 AFIX 13 H3 2 0.355190 0.598993 0.704559 11.00000 -1.20000 AFIX 0 C4 1 0.395100 0.641211 0.881888 11.00000 0.01960 0.01896 = 0.01822 0.00753 0.00763 0.00603 AFIX 13 H4 2 0.346333 0.604571 0.919995 11.00000 -1.20000 AFIX 0 C5 1 0.631002 0.325863 0.785734 11.00000 0.01937 0.02218 = 0.02401 0.01246 0.00996 0.00878 C6 1 0.578117 0.201188 0.717796 11.00000 0.02639 0.02250 = 0.02633 0.01200 0.01089 0.00878 C7 1 0.425422 0.134472 0.645678 11.00000 0.03266 0.02379 = 0.04080 0.01153 0.00652 0.00166 AFIX 137 H7A 2 0.359081 0.181235 0.681054 11.00000 -1.50000 H7B 2 0.417357 0.051567 0.644126 11.00000 -1.50000 H7C 2 0.399728 0.126876 0.564576 11.00000 -1.50000 AFIX 0 C8 1 0.785692 0.350716 0.845090 11.00000 0.02021 0.02836 = 0.03070 0.01611 0.00819 0.00672 AFIX 43 H8 2 0.838815 0.431910 0.896664 11.00000 -1.20000 AFIX 0 C9 1 0.849726 0.247450 0.820918 11.00000 0.02546 0.03762 = 0.03579 0.02257 0.01496 0.01614 C10 1 0.409117 0.375098 0.590325 11.00000 0.02174 0.01829 = 0.01980 0.00834 0.00889 0.00744 C11 1 0.271303 0.311633 0.498176 11.00000 0.02458 0.01951 = 0.02256 0.00784 0.00818 0.00668 AFIX 43 H11 2 0.183973 0.307700 0.513218 11.00000 -1.20000 AFIX 0 C12 1 0.276191 0.257591 0.387512 11.00000 0.03323 0.02519 = 0.02114 0.00824 0.00867 0.01083 C13 1 0.155914 0.185692 0.270349 11.00000 0.04469 0.03410 = 0.02177 0.00432 0.00476 0.01327 AFIX 137 H13A 2 0.063614 0.181144 0.282579 11.00000 -1.50000 H13B 2 0.176142 0.101618 0.233572 11.00000 -1.50000 H13C 2 0.149398 0.227339 0.218345 11.00000 -1.50000 AFIX 0 C14 1 0.518611 0.371002 0.546452 11.00000 0.02729 0.02634 = 0.02434 0.01198 0.01344 0.01009 C15 1 0.675320 0.429759 0.608563 11.00000 0.02623 0.03857 = 0.03574 0.01903 0.01667 0.00738 AFIX 137 H15A 2 0.688418 0.498572 0.684986 11.00000 -1.50000 H15B 2 0.705572 0.461257 0.559617 11.00000 -1.50000 H15C 2 0.734639 0.367943 0.621777 11.00000 -1.50000 AFIX 0 C16 1 0.352697 0.768484 0.903414 11.00000 0.02221 0.01970 = 0.01762 0.00617 0.00591 0.00683 C17 1 0.392640 0.841058 0.853505 11.00000 0.03040 0.02429 = 0.02598 0.01063 0.00894 0.00611 AFIX 43 H17 2 0.451209 0.812228 0.806788 11.00000 -1.20000 AFIX 0 C18 1 0.347453 0.955214 0.871566 11.00000 0.03701 0.02422 = 0.03403 0.01502 0.00264 0.00506 AFIX 43 H18 2 0.375911 1.004620 0.838022 11.00000 -1.20000 AFIX 0 C19 1 0.260667 0.996820 0.938718 11.00000 0.03654 0.02125 = 0.03930 0.00654 0.00177 0.01371 AFIX 43 H19 2 0.227627 1.073911 0.949718 11.00000 -1.20000 AFIX 0 C20 1 0.222397 0.925973 0.989541 11.00000 0.03993 0.03180 = 0.03633 0.00585 0.01573 0.01830 AFIX 43 H20 2 0.163901 0.955242 1.036257 11.00000 -1.20000 AFIX 0 C21 1 0.268515 0.812203 0.973127 11.00000 0.03343 0.02835 = 0.02661 0.00923 0.01405 0.01266 AFIX 43 H21 2 0.242706 0.764590 1.009296 11.00000 -1.20000 AFIX 0 C22 1 0.147272 0.433113 0.761479 11.00000 0.02665 0.04163 = 0.03869 0.01200 0.01348 -0.00317 AFIX 137 H22A 2 0.140287 0.495478 0.834460 11.00000 -1.50000 H22B 2 0.220112 0.382566 0.781381 11.00000 -1.50000 H22C 2 0.052604 0.379683 0.711119 11.00000 -1.50000 AFIX 0 C23 1 0.088579 0.575122 0.669336 11.00000 0.02790 0.03961 = 0.04077 0.00852 -0.00028 0.01766 AFIX 137 H23A 2 -0.007849 0.525355 0.617609 11.00000 -1.50000 H23B 2 0.122899 0.615740 0.628433 11.00000 -1.50000 H23C 2 0.082606 0.638272 0.742370 11.00000 -1.50000 PART 2 -21.00 AFIX 0 C24 1 0.081398 0.941792 0.582100 -21.00000 0.06876 0.07894 = 0.06856 0.03962 0.01415 -0.00105 AFIX 23 H24A 2 0.158021 1.008077 0.650498 -21.00000 -1.20000 H24B 2 0.011832 0.919226 0.613309 -21.00000 -1.20000 AFIX 0 C25 1 0.147730 0.838309 0.542707 -21.00000 0.06967 0.07566 = 0.06510 0.03422 0.00438 -0.00032 AFIX 137 H25A 2 0.073742 0.768006 0.479350 -21.00000 -1.50000 H25B 2 0.196854 0.816939 0.608796 -21.00000 -1.50000 H25C 2 0.219113 0.857411 0.512348 -21.00000 -1.50000 PART 1 21.00 AFIX 0 C26 1 0.054233 0.894400 0.471612 21.00000 0.07256 0.07982 = 0.06766 0.04376 0.01099 0.00483 AFIX 23 H26A 2 0.125916 0.903642 0.436469 21.00000 -1.20000 H26B 2 -0.026511 0.828626 0.407361 21.00000 -1.20000 AFIX 0 C27 1 0.128119 0.843203 0.563043 21.00000 0.06321 0.07906 = 0.06433 0.04233 0.00952 -0.00244 AFIX 137 H27A 2 0.214275 0.902578 0.625027 21.00000 -1.50000 H27B 2 0.157269 0.763936 0.523499 21.00000 -1.50000 H27C 2 0.059824 0.830523 0.598775 21.00000 -1.50000 PART 0 AFIX 0 C28 1 1.007123 0.238203 0.870555 11.00000 0.02915 0.05559 = 0.05953 0.03490 0.01785 0.02321 AFIX 137 H28A 2 1.065453 0.321488 0.912876 11.00000 -1.50000 H28B 2 1.038610 0.187721 0.805723 11.00000 -1.50000 H28C 2 1.020179 0.199356 0.925508 11.00000 -1.50000 AFIX 0 HKLF 4 REM ColourChem_DZ050_0m_a.res in P-1 REM R1 = 0.0519 for 5853 Fo > 4sig(Fo) and 0.0778 for all 8011 data REM 331 parameters refined using 54 restraints END WGHT 0.0672 0.7815 REM Highest difference peak 0.823, deepest hole -1.120, 1-sigma level 0.080 Q1 1 0.5807 0.6815 1.0192 11.00000 0.05 0.48 Q2 1 0.8111 0.1854 0.7651 11.00000 0.05 0.45 Q3 1 0.6449 0.6770 0.9329 11.00000 0.05 0.44 Q4 1 0.2606 0.2742 0.4447 11.00000 0.05 0.40 Q5 1 0.6008 0.6368 0.8811 11.00000 0.05 0.39 Q6 1 -0.0617 0.8970 0.4172 11.00000 0.05 0.38 Q7 1 0.4642 0.3760 0.5749 11.00000 0.05 0.38 Q8 1 0.0951 1.0342 0.4626 11.00000 0.05 0.36 Q9 1 0.4115 0.4041 0.6571 11.00000 0.05 0.36 Q10 1 0.3762 0.5990 0.8175 11.00000 0.05 0.35 Q11 1 0.2183 0.2384 0.3412 11.00000 0.05 0.34 Q12 1 0.5831 0.3762 0.7870 11.00000 0.05 0.33 Q13 1 0.3829 0.2586 0.3992 11.00000 0.05 0.32 Q14 1 0.2424 0.8637 0.9697 11.00000 0.05 0.31 Q15 1 0.6294 0.1587 0.7214 11.00000 0.05 0.30 Q16 1 0.2520 0.5205 0.7363 11.00000 0.05 0.29 Q17 1 0.7198 0.0817 0.6497 11.00000 0.05 0.29 Q18 1 0.3748 0.6978 0.8912 11.00000 0.05 0.29 Q19 1 0.8185 0.2933 0.8397 11.00000 0.05 0.28 Q20 1 0.4725 0.3250 0.4898 11.00000 0.05 0.28 ; _shelx_res_checksum 61150 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.58497(5) 0.65186(4) 0.95084(4) 0.02065(11) Uani 1 1 d . . . . . S2 S 0.71976(6) 0.11741(5) 0.72467(5) 0.03134(14) Uani 1 1 d . . . . . S3 S 0.45247(7) 0.28499(6) 0.39467(5) 0.03238(14) Uani 1 1 d . . . . . N1 N 0.18994(18) 0.49473(16) 0.69851(15) 0.0249(3) Uani 1 1 d . . . . . O1 O 0.63090(16) 0.71421(13) 1.07697(12) 0.0282(3) Uani 1 1 d . . . . . O2 O 0.66356(15) 0.68777(13) 0.89138(13) 0.0262(3) Uani 1 1 d . . . . . O3 O 0.58845(15) 0.50804(12) 0.92290(11) 0.0215(3) Uani 1 1 d . . . . . O4 O 0.000000 1.000000 0.500000 0.0999(12) Uani 1 2 d S U P . . C1 C 0.5418(2) 0.42454(17) 0.80027(16) 0.0189(3) Uani 1 1 d . . . . . C2 C 0.4346(2) 0.44505(16) 0.71872(16) 0.0183(3) Uani 1 1 d . . . . . C3 C 0.3444(2) 0.54895(17) 0.74791(16) 0.0185(3) Uani 1 1 d . . . . . H3 H 0.355190 0.598993 0.704559 0.022 Uiso 1 1 calc R U . . . C4 C 0.3951(2) 0.64121(17) 0.88189(16) 0.0188(3) Uani 1 1 d . . . . . H4 H 0.346333 0.604571 0.919995 0.023 Uiso 1 1 calc R U . . . C5 C 0.6310(2) 0.32586(18) 0.78573(17) 0.0203(4) Uani 1 1 d . . . . . C6 C 0.5781(2) 0.20119(18) 0.71780(18) 0.0241(4) Uani 1 1 d . . . . . C7 C 0.4254(3) 0.1345(2) 0.6457(2) 0.0351(5) Uani 1 1 d . . . . . H7A H 0.359081 0.181235 0.681054 0.053 Uiso 1 1 calc R U . . . H7B H 0.417357 0.051567 0.644126 0.053 Uiso 1 1 calc R U . . . H7C H 0.399728 0.126876 0.564576 0.053 Uiso 1 1 calc R U . . . C8 C 0.7857(2) 0.3507(2) 0.84509(18) 0.0255(4) Uani 1 1 d . . . . . H8 H 0.838815 0.431910 0.896664 0.031 Uiso 1 1 calc R U . . . C9 C 0.8497(2) 0.2475(2) 0.8209(2) 0.0294(4) Uani 1 1 d . . . . . C10 C 0.4091(2) 0.37510(17) 0.59032(16) 0.0194(3) Uani 1 1 d . . . . . C11 C 0.2713(2) 0.31163(17) 0.49818(17) 0.0227(4) Uani 1 1 d . . . . . H11 H 0.183973 0.307700 0.513218 0.027 Uiso 1 1 calc R U . . . C12 C 0.2762(2) 0.25759(19) 0.38751(18) 0.0273(4) Uani 1 1 d . . . . . C13 C 0.1559(3) 0.1857(2) 0.27035(19) 0.0380(5) Uani 1 1 d . . . . . H13A H 0.063614 0.181144 0.282579 0.057 Uiso 1 1 calc R U . . . H13B H 0.176142 0.101618 0.233572 0.057 Uiso 1 1 calc R U . . . H13C H 0.149398 0.227339 0.218345 0.057 Uiso 1 1 calc R U . . . C14 C 0.5186(2) 0.37100(19) 0.54645(17) 0.0244(4) Uani 1 1 d . . . . . C15 C 0.6753(2) 0.4298(2) 0.6086(2) 0.0309(5) Uani 1 1 d . . . . . H15A H 0.688418 0.498572 0.684986 0.046 Uiso 1 1 calc R U . . . H15B H 0.705572 0.461257 0.559617 0.046 Uiso 1 1 calc R U . . . H15C H 0.734639 0.367943 0.621777 0.046 Uiso 1 1 calc R U . . . C16 C 0.3527(2) 0.76848(17) 0.90341(16) 0.0208(4) Uani 1 1 d . . . . . C17 C 0.3926(2) 0.84106(19) 0.85351(18) 0.0272(4) Uani 1 1 d . . . . . H17 H 0.451209 0.812228 0.806788 0.033 Uiso 1 1 calc R U . . . C18 C 0.3475(3) 0.9552(2) 0.8716(2) 0.0337(5) Uani 1 1 d . . . . . H18 H 0.375911 1.004620 0.838022 0.040 Uiso 1 1 calc R U . . . C19 C 0.2607(3) 0.9968(2) 0.9387(2) 0.0377(6) Uani 1 1 d . . . . . H19 H 0.227627 1.073911 0.949718 0.045 Uiso 1 1 calc R U . . . C20 C 0.2224(3) 0.9260(2) 0.9895(2) 0.0383(5) Uani 1 1 d . . . . . H20 H 0.163901 0.955242 1.036257 0.046 Uiso 1 1 calc R U . . . C21 C 0.2685(2) 0.8122(2) 0.97313(19) 0.0293(4) Uani 1 1 d . . . . . H21 H 0.242706 0.764590 1.009296 0.035 Uiso 1 1 calc R U . . . C22 C 0.1473(3) 0.4331(2) 0.7615(2) 0.0370(5) Uani 1 1 d . . . . . H22A H 0.140287 0.495478 0.834460 0.056 Uiso 1 1 calc R U . . . H22B H 0.220112 0.382566 0.781381 0.056 Uiso 1 1 calc R U . . . H22C H 0.052604 0.379683 0.711119 0.056 Uiso 1 1 calc R U . . . C23 C 0.0886(3) 0.5751(2) 0.6693(2) 0.0424(6) Uani 1 1 d . . . . . H23A H -0.007849 0.525355 0.617609 0.064 Uiso 1 1 calc R U . . . H23B H 0.122899 0.615740 0.628433 0.064 Uiso 1 1 calc R U . . . H23C H 0.082606 0.638272 0.742370 0.064 Uiso 1 1 calc R U . . . C24 C 0.0814(8) 0.9418(7) 0.5821(7) 0.0723(13) Uani 0.539(6) 1 d . U P A 2 H24A H 0.158021 1.008077 0.650498 0.087 Uiso 0.539(6) 1 calc R U P A 2 H24B H 0.011832 0.919226 0.613309 0.087 Uiso 0.539(6) 1 calc R U P A 2 C25 C 0.1477(18) 0.8383(15) 0.5427(12) 0.074(2) Uani 0.539(6) 1 d . U P A 2 H25A H 0.073742 0.768006 0.479350 0.111 Uiso 0.539(6) 1 calc R U P A 2 H25B H 0.196854 0.816939 0.608796 0.111 Uiso 0.539(6) 1 calc R U P A 2 H25C H 0.219113 0.857411 0.512348 0.111 Uiso 0.539(6) 1 calc R U P A 2 C26 C 0.0542(10) 0.8944(8) 0.4716(8) 0.0731(13) Uani 0.461(6) 1 d . U P A 1 H26A H 0.125916 0.903642 0.436469 0.088 Uiso 0.461(6) 1 calc R U P A 1 H26B H -0.026511 0.828626 0.407361 0.088 Uiso 0.461(6) 1 calc R U P A 1 C27 C 0.1281(19) 0.8432(19) 0.5630(14) 0.069(2) Uani 0.461(6) 1 d . U P A 1 H27A H 0.214275 0.902578 0.625027 0.103 Uiso 0.461(6) 1 calc R U P A 1 H27B H 0.157269 0.763936 0.523499 0.103 Uiso 0.461(6) 1 calc R U P A 1 H27C H 0.059824 0.830523 0.598775 0.103 Uiso 0.461(6) 1 calc R U P A 1 C28 C 1.0071(3) 0.2382(3) 0.8706(3) 0.0439(6) Uani 1 1 d . . . . . H28A H 1.065453 0.321488 0.912876 0.066 Uiso 1 1 calc R U . . . H28B H 1.038610 0.187721 0.805723 0.066 Uiso 1 1 calc R U . . . H28C H 1.020179 0.199356 0.925508 0.066 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 0.0207(2) 0.0193(2) 0.0190(2) 0.00671(16) 0.00519(17) 0.00506(16) S2 0.0371(3) 0.0267(3) 0.0348(3) 0.0145(2) 0.0163(2) 0.0185(2) S3 0.0376(3) 0.0409(3) 0.0232(2) 0.0124(2) 0.0176(2) 0.0155(2) N1 0.0179(8) 0.0275(9) 0.0241(8) 0.0083(7) 0.0046(6) 0.0084(6) O1 0.0288(8) 0.0272(7) 0.0191(7) 0.0052(6) 0.0027(6) 0.0073(6) O2 0.0235(7) 0.0241(7) 0.0306(7) 0.0109(6) 0.0102(6) 0.0035(5) O3 0.0244(7) 0.0207(6) 0.0184(6) 0.0091(5) 0.0055(5) 0.0078(5) O4 0.086(2) 0.095(2) 0.090(2) 0.039(2) -0.0030(19) 0.0068(19) C1 0.0186(8) 0.0177(8) 0.0202(8) 0.0070(6) 0.0081(7) 0.0043(6) C2 0.0192(8) 0.0167(8) 0.0196(8) 0.0066(6) 0.0091(7) 0.0045(6) C3 0.0193(8) 0.0184(8) 0.0177(8) 0.0073(6) 0.0068(7) 0.0064(6) C4 0.0196(8) 0.0190(8) 0.0182(8) 0.0075(6) 0.0076(7) 0.0060(6) C5 0.0194(8) 0.0222(9) 0.0240(9) 0.0125(7) 0.0100(7) 0.0088(7) C6 0.0264(10) 0.0225(9) 0.0263(9) 0.0120(7) 0.0109(8) 0.0088(7) C7 0.0327(12) 0.0238(10) 0.0408(12) 0.0115(9) 0.0065(10) 0.0017(8) C8 0.0202(9) 0.0284(10) 0.0307(10) 0.0161(8) 0.0082(8) 0.0067(7) C9 0.0255(10) 0.0376(12) 0.0358(11) 0.0226(9) 0.0150(9) 0.0161(9) C10 0.0217(9) 0.0183(8) 0.0198(8) 0.0083(7) 0.0089(7) 0.0074(7) C11 0.0246(9) 0.0195(9) 0.0226(9) 0.0078(7) 0.0082(8) 0.0067(7) C12 0.0332(11) 0.0252(10) 0.0211(9) 0.0082(7) 0.0087(8) 0.0108(8) C13 0.0447(14) 0.0341(12) 0.0218(10) 0.0043(9) 0.0048(10) 0.0133(10) C14 0.0273(10) 0.0263(10) 0.0243(9) 0.0120(7) 0.0134(8) 0.0101(8) C15 0.0262(10) 0.0386(12) 0.0357(11) 0.0190(9) 0.0167(9) 0.0074(9) C16 0.0222(9) 0.0197(9) 0.0176(8) 0.0062(7) 0.0059(7) 0.0068(7) C17 0.0304(11) 0.0243(10) 0.0260(10) 0.0106(8) 0.0089(9) 0.0061(8) C18 0.0370(12) 0.0242(10) 0.0340(11) 0.0150(9) 0.0026(10) 0.0051(9) C19 0.0365(12) 0.0213(10) 0.0393(12) 0.0065(9) 0.0018(10) 0.0137(9) C20 0.0399(13) 0.0318(12) 0.0363(12) 0.0058(9) 0.0157(11) 0.0183(10) C21 0.0334(11) 0.0283(10) 0.0266(10) 0.0092(8) 0.0141(9) 0.0127(8) C22 0.0267(11) 0.0416(13) 0.0387(12) 0.0120(10) 0.0135(10) -0.0032(9) C23 0.0279(12) 0.0396(13) 0.0408(13) 0.0085(11) -0.0003(10) 0.0177(10) C24 0.069(3) 0.079(3) 0.069(2) 0.040(2) 0.014(2) -0.001(2) C25 0.070(4) 0.076(3) 0.065(4) 0.034(3) 0.004(3) 0.000(3) C26 0.073(3) 0.080(3) 0.068(2) 0.044(2) 0.011(2) 0.005(2) C27 0.063(4) 0.079(3) 0.064(4) 0.042(3) 0.010(3) -0.002(3) C28 0.0291(12) 0.0556(16) 0.0595(17) 0.0349(14) 0.0179(12) 0.0232(11) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 O1 S1 O2 119.33(10) . . O1 S1 O3 104.79(8) . . O2 S1 O3 109.40(8) . . O1 S1 C4 111.51(9) . . O2 S1 C4 111.22(9) . . O3 S1 C4 98.24(9) . . C9 S2 C6 93.45(11) . . C14 S3 C12 93.32(10) . . C22 N1 C23 112.51(19) . . C22 N1 C3 115.09(17) . . C23 N1 C3 115.21(18) . . C1 O3 S1 115.64(12) . . C26 O4 C26 180.0 2_576 . C26 O4 C24 51.9(4) 2_576 2_576 C26 O4 C24 128.1(4) . 2_576 C24 O4 C24 180.0(4) 2_576 . C2 C1 O3 120.74(16) . . C2 C1 C5 130.12(17) . . O3 C1 C5 109.11(15) . . C1 C2 C10 120.16(16) . . C1 C2 C3 124.30(16) . . C10 C2 C3 115.12(16) . . N1 C3 C2 109.40(15) . . N1 C3 C4 112.30(15) . . C2 C3 C4 115.10(15) . . N1 C3 H3 106.5 . . C2 C3 H3 106.5 . . C4 C3 H3 106.5 . . C16 C4 C3 113.95(15) . . C16 C4 S1 111.41(13) . . C3 C4 S1 109.74(12) . . C16 C4 H4 107.1 . . C3 C4 H4 107.1 . . S1 C4 H4 107.1 . . C6 C5 C8 112.55(18) . . C6 C5 C1 125.06(18) . . C8 C5 C1 122.36(17) . . C5 C6 C7 130.40(19) . . C5 C6 S2 110.05(16) . . C7 C6 S2 119.55(16) . . C6 C7 H7A 109.5 . . C6 C7 H7B 109.5 . . H7A C7 H7B 109.5 . . C6 C7 H7C 109.5 . . H7A C7 H7C 109.5 . . H7B C7 H7C 109.5 . . C9 C8 C5 113.92(19) . . C9 C8 H8 123.0 . . C5 C8 H8 123.0 . . C8 C9 C28 128.3(2) . . C8 C9 S2 110.00(16) . . C28 C9 S2 121.59(19) . . C14 C10 C11 112.14(17) . . C14 C10 C2 122.05(17) . . C11 C10 C2 125.71(16) . . C12 C11 C10 114.34(18) . . C12 C11 H11 122.8 . . C10 C11 H11 122.8 . . C11 C12 C13 129.8(2) . . C11 C12 S3 109.74(16) . . C13 C12 S3 120.44(16) . . C12 C13 H13A 109.5 . . C12 C13 H13B 109.5 . . H13A C13 H13B 109.5 . . C12 C13 H13C 109.5 . . H13A C13 H13C 109.5 . . H13B C13 H13C 109.5 . . C10 C14 C15 130.37(18) . . C10 C14 S3 110.41(15) . . C15 C14 S3 119.20(15) . . C14 C15 H15A 109.5 . . C14 C15 H15B 109.5 . . H15A C15 H15B 109.5 . . C14 C15 H15C 109.5 . . H15A C15 H15C 109.5 . . H15B C15 H15C 109.5 . . C21 C16 C17 119.37(19) . . C21 C16 C4 118.56(18) . . C17 C16 C4 122.05(17) . . C18 C17 C16 120.5(2) . . C18 C17 H17 119.7 . . C16 C17 H17 119.7 . . C19 C18 C17 119.8(2) . . C19 C18 H18 120.1 . . C17 C18 H18 120.1 . . C20 C19 C18 119.9(2) . . C20 C19 H19 120.1 . . C18 C19 H19 120.1 . . C19 C20 C21 120.8(2) . . C19 C20 H20 119.6 . . C21 C20 H20 119.6 . . C20 C21 C16 119.7(2) . . C20 C21 H21 120.2 . . C16 C21 H21 120.2 . . N1 C22 H22A 109.5 . . N1 C22 H22B 109.5 . . H22A C22 H22B 109.5 . . N1 C22 H22C 109.5 . . H22A C22 H22C 109.5 . . H22B C22 H22C 109.5 . . N1 C23 H23A 109.5 . . N1 C23 H23B 109.5 . . H23A C23 H23B 109.5 . . N1 C23 H23C 109.5 . . H23A C23 H23C 109.5 . . H23B C23 H23C 109.5 . . C25 C24 O4 121.8(8) . . C25 C24 H24A 106.9 . . O4 C24 H24A 106.9 . . C25 C24 H24B 106.9 . . O4 C24 H24B 106.9 . . H24A C24 H24B 106.7 . . C24 C25 H25A 109.5 . . C24 C25 H25B 109.5 . . H25A C25 H25B 109.5 . . C24 C25 H25C 109.5 . . H25A C25 H25C 109.5 . . H25B C25 H25C 109.5 . . O4 C26 C27 122.6(9) . . O4 C26 H26A 106.7 . . C27 C26 H26A 106.7 . . O4 C26 H26B 106.7 . . C27 C26 H26B 106.7 . . H26A C26 H26B 106.6 . . C26 C27 H27A 109.5 . . C26 C27 H27B 109.5 . . H27A C27 H27B 109.5 . . C26 C27 H27C 109.5 . . H27A C27 H27C 109.5 . . H27B C27 H27C 109.5 . . C9 C28 H28A 109.5 . . C9 C28 H28B 109.5 . . H28A C28 H28B 109.5 . . C9 C28 H28C 109.5 . . H28A C28 H28C 109.5 . . H28B C28 H28C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 O1 1.4283(15) . S1 O2 1.4327(15) . S1 O3 1.6049(16) . S1 C4 1.772(2) . S2 C9 1.724(3) . S2 C6 1.727(2) . S3 C14 1.726(2) . S3 C12 1.730(2) . N1 C22 1.451(3) . N1 C23 1.459(3) . N1 C3 1.467(3) . O3 C1 1.428(2) . O4 C26 1.335(9) 2_576 O4 C26 1.335(9) . O4 C24 1.528(7) 2_576 O4 C24 1.528(7) . C1 C2 1.343(3) . C1 C5 1.467(3) . C2 C10 1.490(2) . C2 C3 1.532(3) . C3 C4 1.563(3) . C3 H3 1.0000 . C4 C16 1.518(3) . C4 H4 1.0000 . C5 C6 1.377(3) . C5 C8 1.432(3) . C6 C7 1.495(3) . C7 H7A 0.9800 . C7 H7B 0.9800 . C7 H7C 0.9800 . C8 C9 1.362(3) . C8 H8 0.9500 . C9 C28 1.499(3) . C10 C14 1.376(3) . C10 C11 1.434(3) . C11 C12 1.359(3) . C11 H11 0.9500 . C12 C13 1.500(3) . C13 H13A 0.9800 . C13 H13B 0.9800 . C13 H13C 0.9800 . C14 C15 1.496(3) . C15 H15A 0.9800 . C15 H15B 0.9800 . C15 H15C 0.9800 . C16 C21 1.393(3) . C16 C17 1.394(3) . C17 C18 1.389(3) . C17 H17 0.9500 . C18 C19 1.387(4) . C18 H18 0.9500 . C19 C20 1.381(4) . C19 H19 0.9500 . C20 C21 1.391(3) . C20 H20 0.9500 . C21 H21 0.9500 . C22 H22A 0.9800 . C22 H22B 0.9800 . C22 H22C 0.9800 . C23 H23A 0.9800 . C23 H23B 0.9800 . C23 H23C 0.9800 . C24 C25 1.397(18) . C24 H24A 0.9900 . C24 H24B 0.9900 . C25 H25A 0.9800 . C25 H25B 0.9800 . C25 H25C 0.9800 . C26 C27 1.54(2) . C26 H26A 0.9900 . C26 H26B 0.9900 . C27 H27A 0.9800 . C27 H27B 0.9800 . C27 H27C 0.9800 . C28 H28A 0.9800 . C28 H28B 0.9800 . C28 H28C 0.9800 .