#------------------------------------------------------------------------------ #$Date: 2019-11-08 03:39:00 +0200 (Fri, 08 Nov 2019) $ #$Revision: 225134 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156742.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_7156742 loop_ _publ_author_name 'Mariappan, Arumugam' 'Rajaguru, Kandasamy' 'Muthusubramanian, Shanmugam' 'Bhuvanesh, Nattamai' _publ_section_title ; A facile one pot synthesis of thiazolo[3,2-a]benzimidazole and pyran fused polyheterocyclic scaffolds. ; _journal_issue 17 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4196 _journal_page_last 4199 _journal_paper_doi 10.1039/c9ob00300b _journal_volume 17 _journal_year 2019 _chemical_formula_moiety 'C27 H21 Cl N4 O S, C H4 O' _chemical_formula_sum 'C28 H25 Cl N4 O2 S' _chemical_formula_weight 517.03 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2016-02-04 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133) ; _audit_update_record ; 2019-02-05 deposited with the CCDC. 2019-03-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.472(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 23.3244(7) _cell_length_b 9.7484(3) _cell_length_c 23.6714(7) _cell_measurement_reflns_used 9864 _cell_measurement_temperature 99.99 _cell_measurement_theta_max 70.129 _cell_measurement_theta_min 3.974 _cell_volume 5134.0(3) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _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_temperature 99.99 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.1062 _diffrn_reflns_av_unetI/netI 0.0489 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 81633 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.123 _diffrn_reflns_theta_min 2.332 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.344 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.5020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1316 before and 0.0768 after correction. The Ratio of minimum to maximum transmission is 0.6664. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.338 _exptl_crystal_description block _exptl_crystal_F_000 2160 _exptl_crystal_size_max 0.657 _exptl_crystal_size_mid 0.155 _exptl_crystal_size_min 0.058 _refine_diff_density_max 1.052 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.070 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 655 _refine_ls_number_reflns 9721 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0549 _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^)+(0.0355P)^2^+8.6478P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1081 _refine_ls_wR_factor_ref 0.1168 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7595 _reflns_number_total 9721 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob00300b2.cif _cod_data_source_block bimth _cod_depositor_comments 'Adding full bibliography for 7156742.cif.' _cod_database_code 7156742 _shelxl_version_number 2014/6 _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 0.876 _shelx_estimated_absorpt_t_min 0.308 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Riding coordinates: N1(H1A,H1B), O1S(H1S) 2.b Rotating group: N1B(H1BA,H1BB) 2.c Ternary CH refined with riding coordinates: C3(H3), C4(H4), C3B(H3B), C4B(H4B) 2.d Secondary CH2 refined with riding coordinates: C20(H20A,H20B), C20B(H20C,H20D) 2.e Aromatic/amide H refined with riding coordinates: C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19), C23(H23), C24(H24), C26(H26), C27(H27), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B), C15B(H15B), C16B(H16B), C18B(H18B), C19B(H19B), C23B(H23B), C24B(H24B), C26B(H26B), C27B(H27B) 2.f Idealised Me refined as rotating group: C21(H21A,H21B,H21C), C21B(H21D,H21E,H21F), C2S(H2SA,H2SB,H2SC), C6S(H6SA,H6SB, H6SC) 2.g Idealised tetrahedral OH refined as rotating group: O5S(H5S) ; _shelx_res_file ; TITL bimth_a.res in P2(1)/n REM Old TITL BIMTH in P21/n #14 REM SHELXT solution in P2(1)/n REM R1 0.128, Rweak 0.010, Alpha 0.036, Orientation as input REM Formula found by SHELXT: C56 N6 O6 S2 Cl2 CELL 1.54178 23.3244 9.7484 23.6714 90 107.472 90 ZERR 8 0.0007 0.0003 0.0007 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O S UNIT 224 200 8 32 16 8 L.S. 10 PLAN 20 SIZE 0.058 0.155 0.657 TEMP -173.16 BOND $H acta more -1 wpdb -1 htab conf fmap 2 OMIT -3 0 21 REM REM REM WGHT 0.035500 8.647800 FVAR 0.25028 CL1 3 0.681053 0.166577 0.461979 11.00000 0.02854 0.02667 = 0.01713 0.00428 0.01347 0.00967 S1 6 0.666192 0.380803 0.800244 11.00000 0.02036 0.01656 = 0.01403 -0.00283 0.00452 0.00300 O1 5 0.591942 0.146797 0.703802 11.00000 0.01241 0.01588 = 0.01452 0.00314 0.00481 -0.00114 N1 4 0.573260 -0.033045 0.751757 11.00000 0.01107 0.01474 = 0.02031 0.00312 0.00384 -0.00265 AFIX 3 0.8870 H1A 2 0.580500 -0.110545 0.772317 11.00000 -1.20000 H1B 2 0.536060 -0.039105 0.727517 11.00000 -1.20000 AFIX 0 N2 4 0.710564 -0.152512 0.848998 11.00000 0.02219 0.02344 = 0.03667 0.01171 0.00093 -0.00188 N3 4 0.591821 0.380705 0.693056 11.00000 0.01286 0.01369 = 0.01556 -0.00180 0.00486 0.00108 N4 4 0.559608 0.525537 0.751073 11.00000 0.02217 0.01493 = 0.01971 0.00024 0.01133 0.00342 C1 1 0.616282 0.051865 0.746258 11.00000 0.01782 0.01147 = 0.01384 -0.00221 0.00894 0.00191 C2 1 0.676105 0.047641 0.776337 11.00000 0.01549 0.01235 = 0.01647 -0.00030 0.00703 -0.00068 C3 1 0.719515 0.149404 0.763046 11.00000 0.01280 0.01216 = 0.01420 -0.00193 0.00514 0.00027 AFIX 13 H3 2 0.732019 0.111234 0.729336 11.00000 -1.20000 AFIX 0 C4 1 0.685867 0.283972 0.741476 11.00000 0.01686 0.01212 = 0.01482 -0.00326 0.00825 -0.00075 AFIX 13 H4 2 0.712268 0.343436 0.725428 11.00000 -1.20000 AFIX 0 C5 1 0.626944 0.259754 0.691813 11.00000 0.01493 0.00905 = 0.01776 0.00050 0.00711 0.00124 C6 1 0.601523 0.439865 0.747875 11.00000 0.01929 0.01257 = 0.01715 0.00056 0.00743 0.00007 C7 1 0.517164 0.519228 0.694380 11.00000 0.01948 0.01636 = 0.02048 0.00236 0.01055 0.00064 C8 1 0.536071 0.427202 0.658028 11.00000 0.01289 0.01489 = 0.02321 0.00339 0.00920 0.00304 C9 1 0.463186 0.589815 0.672554 11.00000 0.02329 0.01970 = 0.03290 0.00266 0.01715 0.00754 AFIX 43 H9 2 0.450002 0.652983 0.696589 11.00000 -1.20000 AFIX 0 C10 1 0.429492 0.564826 0.614780 11.00000 0.01706 0.03032 = 0.03294 0.00754 0.00732 0.01031 AFIX 43 H10 2 0.392374 0.611544 0.598965 11.00000 -1.20000 AFIX 0 C11 1 0.448432 0.472932 0.579006 11.00000 0.02214 0.02614 = 0.02387 0.00482 0.00296 0.00526 AFIX 43 H11 2 0.423950 0.458639 0.539413 11.00000 -1.20000 AFIX 0 C12 1 0.502494 0.401334 0.599898 11.00000 0.01745 0.02030 = 0.02239 -0.00061 0.00674 0.00239 AFIX 43 H12 2 0.515557 0.338437 0.575674 11.00000 -1.20000 AFIX 0 C13 1 0.695744 -0.061031 0.816978 11.00000 0.01157 0.01860 = 0.02388 -0.00030 0.00406 -0.00290 C14 1 0.776724 0.176077 0.813708 11.00000 0.01479 0.00875 = 0.01600 -0.00107 0.00398 0.00184 C15 1 0.778100 0.180544 0.872957 11.00000 0.01734 0.01118 = 0.01663 0.00016 0.00668 0.00185 AFIX 43 H15 2 0.742414 0.163885 0.883343 11.00000 -1.20000 AFIX 0 C16 1 0.831447 0.209259 0.916909 11.00000 0.02214 0.01019 = 0.01581 -0.00089 0.00682 0.00313 AFIX 43 H16 2 0.831490 0.212130 0.957037 11.00000 -1.20000 AFIX 0 C17 1 0.884934 0.233982 0.903704 11.00000 0.01600 0.01032 = 0.02106 -0.00098 0.00217 0.00110 C18 1 0.883111 0.230222 0.844405 11.00000 0.01434 0.01409 = 0.02367 0.00014 0.00780 -0.00016 AFIX 43 H18 2 0.918764 0.247465 0.834041 11.00000 -1.20000 AFIX 0 C19 1 0.829992 0.201656 0.800103 11.00000 0.01766 0.01182 = 0.01515 0.00227 0.00575 0.00189 AFIX 43 H19 2 0.829928 0.199503 0.759961 11.00000 -1.20000 AFIX 0 C20 1 0.942886 0.258630 0.952940 11.00000 0.01798 0.02686 = 0.02568 -0.00547 -0.00035 0.00244 AFIX 23 H20A 2 0.962903 0.169107 0.964859 11.00000 -1.20000 H20B 2 0.932680 0.296127 0.987586 11.00000 -1.20000 AFIX 0 C21 1 0.987736 0.355729 0.937970 11.00000 0.01736 0.03386 = 0.03431 -0.01011 -0.00321 -0.00416 AFIX 137 H21A 2 0.968348 0.444333 0.925131 11.00000 -1.50000 H21B 2 1.001156 0.316043 0.906054 11.00000 -1.50000 H21C 2 1.022448 0.369036 0.973130 11.00000 -1.50000 AFIX 0 C22 1 0.637889 0.235594 0.632760 11.00000 0.01018 0.01501 = 0.01114 -0.00096 0.00252 -0.00025 C23 1 0.645967 0.347813 0.599294 11.00000 0.01327 0.01392 = 0.01546 -0.00018 0.00397 0.00091 AFIX 43 H23 2 0.642432 0.438387 0.612680 11.00000 -1.20000 AFIX 0 C24 1 0.659144 0.327322 0.546539 11.00000 0.01469 0.01683 = 0.01320 0.00352 0.00269 -0.00009 AFIX 43 H24 2 0.664652 0.403348 0.523600 11.00000 -1.20000 AFIX 0 C25 1 0.664146 0.194998 0.527826 11.00000 0.01430 0.02012 = 0.01284 0.00039 0.00564 0.00428 C26 1 0.656705 0.082415 0.560717 11.00000 0.02100 0.01458 = 0.01831 -0.00269 0.00835 0.00349 AFIX 43 H26 2 0.660654 -0.008044 0.547425 11.00000 -1.20000 AFIX 0 C27 1 0.643446 0.103871 0.613168 11.00000 0.01599 0.01320 = 0.01659 0.00163 0.00625 0.00038 AFIX 43 H27 2 0.638096 0.027478 0.635990 11.00000 -1.20000 AFIX 0 CL1B 3 0.276265 0.620693 1.031709 11.00000 0.03414 0.03947 = 0.03365 -0.01880 0.02595 -0.01302 S1B 6 0.338597 0.422319 0.714248 11.00000 0.01940 0.01660 = 0.01372 -0.00170 0.00514 0.00166 O1B 5 0.407415 0.662046 0.817759 11.00000 0.01255 0.01624 = 0.01747 0.00550 0.00255 -0.00182 N1B 4 0.433380 0.849979 0.778927 11.00000 0.01539 0.01602 = 0.01954 0.00258 0.00709 -0.00008 AFIX 7 H1BA 2 0.468380 0.806381 0.789441 11.00000 -1.20000 H1BB 2 0.428372 0.889171 0.743966 11.00000 -1.20000 AFIX 0 N2B 4 0.303358 0.972833 0.667768 11.00000 0.01886 0.02261 = 0.02611 0.00637 0.00597 0.00126 N3B 4 0.405513 0.428829 0.824434 11.00000 0.01454 0.01400 = 0.01370 -0.00012 0.00666 0.00202 N4B 4 0.442107 0.276952 0.772371 11.00000 0.02069 0.01654 = 0.01625 -0.00118 0.00768 0.00107 C1B 1 0.388515 0.760486 0.775721 11.00000 0.01577 0.01100 = 0.01669 -0.00235 0.00934 -0.00020 C2B 1 0.331272 0.765876 0.738451 11.00000 0.01483 0.01288 = 0.01534 0.00142 0.00733 0.00026 C3B 1 0.283772 0.662536 0.741548 11.00000 0.01308 0.01453 = 0.01434 -0.00022 0.00612 0.00042 AFIX 13 H3B 2 0.262829 0.699558 0.769481 11.00000 -1.20000 AFIX 0 C4B 1 0.314013 0.527301 0.767583 11.00000 0.01485 0.01415 = 0.01632 -0.00054 0.00841 -0.00178 AFIX 13 H4B 2 0.283870 0.472394 0.780360 11.00000 -1.20000 AFIX 0 C5B 1 0.369100 0.549165 0.822594 11.00000 0.01610 0.01195 = 0.01636 0.00129 0.00713 -0.00068 C6B 1 0.399567 0.364252 0.771421 11.00000 0.01738 0.01403 = 0.01643 0.00095 0.00917 -0.00208 C7B 1 0.481918 0.288674 0.830217 11.00000 0.01955 0.01738 = 0.01798 -0.00001 0.00954 -0.00055 C8B 1 0.460763 0.385668 0.862824 11.00000 0.01429 0.01559 = 0.01682 0.00341 0.00831 0.00191 C9B 1 0.536507 0.223112 0.855922 11.00000 0.02135 0.02024 = 0.02745 0.00124 0.01365 0.00668 AFIX 43 H9B 2 0.551439 0.156240 0.834741 11.00000 -1.20000 AFIX 0 C10B 1 0.568150 0.258396 0.913073 11.00000 0.01941 0.02277 = 0.02828 0.00451 0.00836 0.00554 AFIX 43 H10B 2 0.605556 0.214840 0.931409 11.00000 -1.20000 AFIX 0 C11B 1 0.546852 0.356506 0.944954 11.00000 0.01828 0.02609 = 0.02102 0.00044 0.00486 -0.00024 AFIX 43 H11B 2 0.570133 0.378370 0.984258 11.00000 -1.20000 AFIX 0 C12B 1 0.492385 0.422465 0.920263 11.00000 0.01959 0.02258 = 0.01809 0.00076 0.00891 0.00381 AFIX 43 H12B 2 0.477565 0.489244 0.941575 11.00000 -1.20000 AFIX 0 C13B 1 0.315886 0.879117 0.698926 11.00000 0.00902 0.01861 = 0.01851 -0.00271 0.00531 -0.00127 C14B 1 0.236163 0.635275 0.682680 11.00000 0.01670 0.01039 = 0.01945 0.00222 0.00569 0.00224 C15B 1 0.250044 0.634724 0.629590 11.00000 0.01793 0.01423 = 0.01995 -0.00016 0.00638 0.00048 AFIX 43 H15B 2 0.289673 0.656535 0.629368 11.00000 -1.20000 AFIX 0 C16B 1 0.206427 0.602515 0.576743 11.00000 0.02530 0.01454 = 0.02082 -0.00252 0.00866 0.00117 AFIX 43 H16B 2 0.216799 0.602001 0.540881 11.00000 -1.20000 AFIX 0 C17B 1 0.147745 0.570965 0.575468 11.00000 0.02190 0.01252 = 0.02431 -0.00306 0.00168 0.00167 C18B 1 0.134078 0.572513 0.629032 11.00000 0.01438 0.01395 = 0.02989 0.00046 0.00487 -0.00093 AFIX 43 H18B 2 0.094445 0.550938 0.629315 11.00000 -1.20000 AFIX 0 C19B 1 0.177318 0.604957 0.681697 11.00000 0.01720 0.01347 = 0.02251 0.00198 0.00830 0.00094 AFIX 43 H19B 2 0.166883 0.606626 0.717520 11.00000 -1.20000 AFIX 0 C20B 1 0.100577 0.536054 0.517823 11.00000 0.02550 0.02150 = 0.03062 -0.00693 0.00148 -0.00001 AFIX 23 H20C 2 0.083849 0.444176 0.521258 11.00000 -1.20000 H20D 2 0.119710 0.532020 0.485761 11.00000 -1.20000 AFIX 0 C21B 1 0.049629 0.640104 0.501367 11.00000 0.02988 0.03632 = 0.03851 -0.00798 -0.00625 0.00560 AFIX 137 H21D 2 0.021048 0.615138 0.463135 11.00000 -1.50000 H21E 2 0.066007 0.731533 0.498512 11.00000 -1.50000 H21F 2 0.029015 0.640662 0.531854 11.00000 -1.50000 AFIX 0 C22B 1 0.349592 0.567985 0.877644 11.00000 0.00904 0.01433 = 0.01323 -0.00330 0.00217 0.00031 C23B 1 0.334239 0.698126 0.892651 11.00000 0.01905 0.01613 = 0.02084 -0.00120 0.00735 -0.00009 AFIX 43 H23B 2 0.339922 0.775959 0.870781 11.00000 -1.20000 AFIX 0 C24B 1 0.310615 0.714145 0.939599 11.00000 0.01664 0.02064 = 0.02511 -0.01000 0.00731 0.00071 AFIX 43 H24B 2 0.299377 0.802396 0.949623 11.00000 -1.20000 AFIX 0 C25B 1 0.303709 0.600138 0.971442 11.00000 0.01425 0.02712 = 0.02063 -0.01068 0.01049 -0.00706 C26B 1 0.318890 0.470185 0.957521 11.00000 0.01807 0.02011 = 0.01537 -0.00388 0.00773 -0.00564 AFIX 43 H26B 2 0.314009 0.392905 0.980092 11.00000 -1.20000 AFIX 0 C27B 1 0.341437 0.454884 0.909840 11.00000 0.01198 0.01457 = 0.01732 -0.00327 0.00467 -0.00158 AFIX 43 H27B 2 0.351363 0.366018 0.899201 11.00000 -1.20000 AFIX 0 O1S 5 0.451209 0.059800 0.700935 11.00000 0.01992 0.01460 = 0.02307 -0.00078 0.00977 0.00034 AFIX 3 0.8500 H1S 2 0.447159 0.132720 0.719045 11.00000 -1.50000 AFIX 0 C2S 1 0.426309 0.090377 0.639263 11.00000 0.03571 0.04682 = 0.02674 0.00092 0.01307 -0.00821 AFIX 137 H2SA 2 0.422694 0.005609 0.616199 11.00000 -1.50000 H2SB 2 0.452705 0.154716 0.627161 11.00000 -1.50000 H2SC 2 0.386478 0.131746 0.632199 11.00000 -1.50000 AFIX 0 O5S 5 0.559641 0.743232 0.826724 11.00000 0.02419 0.02020 = 0.02127 -0.00064 0.00937 -0.00131 AFIX 147 H5S 2 0.557213 0.679628 0.802174 11.00000 -1.50000 AFIX 0 C6S 1 0.596463 0.700228 0.883690 11.00000 0.06762 0.06003 = 0.03232 0.00342 0.01412 -0.01803 AFIX 137 H6SA 2 0.633584 0.659375 0.880054 11.00000 -1.50000 H6SB 2 0.574741 0.632166 0.899881 11.00000 -1.50000 H6SC 2 0.606351 0.779608 0.910257 11.00000 -1.50000 AFIX 0 HKLF 4 REM bimth_a.res in P2(1)/n REM R1 = 0.0549 for 7595 Fo > 4sig(Fo) and 0.0746 for all 9721 data REM 655 parameters refined using 0 restraints END WGHT 0.0353 8.6592 REM Instructions for potential hydrogen bonds EQIV $1 x, y-1, z HTAB N1 O5S_$1 HTAB N1 O1S HTAB N1B O5S EQIV $2 x, y+1, z HTAB N1B O1S_$2 EQIV $3 -x+1/2, y-1/2, -z+3/2 HTAB C4B N2B_$3 HTAB O1S N4B HTAB O5S N4 REM Highest difference peak 1.052, deepest hole -0.449, 1-sigma level 0.070 Q1 1 0.6666 0.6782 0.9183 11.00000 0.05 1.05 Q2 1 0.2555 0.6757 1.0036 11.00000 0.05 0.72 Q3 1 0.3767 0.1187 0.5820 11.00000 0.05 0.48 Q4 1 0.3473 0.2251 0.5994 11.00000 0.05 0.41 Q5 1 0.5358 0.0047 0.7471 11.00000 0.05 0.35 Q6 1 0.6788 0.3292 0.7630 11.00000 0.05 0.31 Q7 1 0.4352 0.9353 0.7562 11.00000 0.05 0.29 Q8 1 0.4793 0.3476 0.8479 11.00000 0.05 0.28 Q9 1 0.7007 0.2213 0.7518 11.00000 0.05 0.28 Q10 1 0.3734 0.3766 0.7490 11.00000 0.05 0.27 Q11 1 0.5228 0.4612 0.6742 11.00000 0.05 0.25 Q12 1 0.5618 0.5862 0.7673 11.00000 0.05 0.25 Q13 1 0.1989 0.8854 0.9429 11.00000 0.05 0.25 Q14 1 0.6586 0.2952 0.6301 11.00000 0.05 0.25 Q15 1 0.6195 0.3950 0.7788 11.00000 0.05 0.25 Q16 1 0.1327 0.6100 0.5965 11.00000 0.05 0.24 Q17 1 0.6588 0.3463 0.5786 11.00000 0.05 0.24 Q18 1 0.6392 0.4407 0.7661 11.00000 0.05 0.23 Q19 1 0.3600 0.7756 0.6225 11.00000 0.05 0.23 Q20 1 0.7192 -0.1032 0.8855 11.00000 0.05 0.23 ; _shelx_res_checksum 51213 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 Cl1 Cl 0.68105(3) 0.16658(7) 0.46198(3) 0.02266(16) Uani 1 1 d . S1 S 0.66619(3) 0.38080(7) 0.80024(3) 0.01713(15) Uani 1 1 d . O1 O 0.59194(8) 0.14680(19) 0.70380(8) 0.0141(4) Uani 1 1 d . N1 N 0.57326(10) -0.0330(2) 0.75176(10) 0.0156(5) Uani 1 1 d . H1A H 0.5805 -0.1105 0.7723 0.019 Uiso 1 1 d R H1B H 0.5361 -0.0391 0.7275 0.019 Uiso 1 1 d R N2 N 0.71056(11) -0.1525(3) 0.84900(12) 0.0292(6) Uani 1 1 d . N3 N 0.59182(9) 0.3807(2) 0.69306(9) 0.0139(5) Uani 1 1 d . N4 N 0.55961(10) 0.5255(2) 0.75107(10) 0.0178(5) Uani 1 1 d . C1 C 0.61628(12) 0.0519(3) 0.74626(11) 0.0135(5) Uani 1 1 d . C2 C 0.67611(12) 0.0476(3) 0.77634(11) 0.0143(5) Uani 1 1 d . C3 C 0.71952(11) 0.1494(3) 0.76305(11) 0.0128(5) Uani 1 1 d . H3 H 0.7320 0.1112 0.7293 0.015 Uiso 1 1 calc R C4 C 0.68587(12) 0.2840(3) 0.74148(11) 0.0138(5) Uani 1 1 d . H4 H 0.7123 0.3434 0.7254 0.017 Uiso 1 1 calc R C5 C 0.62694(11) 0.2598(3) 0.69181(11) 0.0134(5) Uani 1 1 d . C6 C 0.60152(12) 0.4399(3) 0.74788(12) 0.0159(6) Uani 1 1 d . C7 C 0.51716(12) 0.5192(3) 0.69438(12) 0.0178(6) Uani 1 1 d . C8 C 0.53607(12) 0.4272(3) 0.65803(12) 0.0162(6) Uani 1 1 d . C9 C 0.46319(13) 0.5898(3) 0.67255(13) 0.0234(6) Uani 1 1 d . H9 H 0.4500 0.6530 0.6966 0.028 Uiso 1 1 calc R C10 C 0.42949(13) 0.5648(3) 0.61478(14) 0.0268(7) Uani 1 1 d . H10 H 0.3924 0.6115 0.5990 0.032 Uiso 1 1 calc R C11 C 0.44843(13) 0.4729(3) 0.57901(13) 0.0249(7) Uani 1 1 d . H11 H 0.4239 0.4586 0.5394 0.030 Uiso 1 1 calc R C12 C 0.50249(12) 0.4013(3) 0.59990(12) 0.0199(6) Uani 1 1 d . H12 H 0.5156 0.3384 0.5757 0.024 Uiso 1 1 calc R C13 C 0.69574(12) -0.0610(3) 0.81698(12) 0.0183(6) Uani 1 1 d . C14 C 0.77672(11) 0.1761(3) 0.81371(11) 0.0133(5) Uani 1 1 d . C15 C 0.77810(12) 0.1805(3) 0.87296(11) 0.0147(5) Uani 1 1 d . H15 H 0.7424 0.1639 0.8833 0.018 Uiso 1 1 calc R C16 C 0.83145(12) 0.2093(3) 0.91691(12) 0.0158(6) Uani 1 1 d . H16 H 0.8315 0.2121 0.9570 0.019 Uiso 1 1 calc R C17 C 0.88493(12) 0.2340(3) 0.90370(12) 0.0165(6) Uani 1 1 d . C18 C 0.88311(12) 0.2302(3) 0.84441(12) 0.0169(6) Uani 1 1 d . H18 H 0.9188 0.2475 0.8340 0.020 Uiso 1 1 calc R C19 C 0.82999(12) 0.2017(3) 0.80010(12) 0.0147(5) Uani 1 1 d . H19 H 0.8299 0.1995 0.7600 0.018 Uiso 1 1 calc R C20 C 0.94289(13) 0.2586(3) 0.95294(13) 0.0250(7) Uani 1 1 d . H20A H 0.9629 0.1691 0.9649 0.030 Uiso 1 1 calc R H20B H 0.9327 0.2961 0.9876 0.030 Uiso 1 1 calc R C21 C 0.98774(13) 0.3557(3) 0.93797(15) 0.0309(7) Uani 1 1 d . H21A H 0.9683 0.4443 0.9251 0.046 Uiso 1 1 calc GR H21B H 1.0012 0.3160 0.9061 0.046 Uiso 1 1 calc GR H21C H 1.0224 0.3690 0.9731 0.046 Uiso 1 1 calc GR C22 C 0.63789(11) 0.2356(3) 0.63276(11) 0.0123(5) Uani 1 1 d . C23 C 0.64597(11) 0.3478(3) 0.59929(11) 0.0143(5) Uani 1 1 d . H23 H 0.6424 0.4384 0.6127 0.017 Uiso 1 1 calc R C24 C 0.65914(11) 0.3273(3) 0.54654(11) 0.0152(5) Uani 1 1 d . H24 H 0.6647 0.4033 0.5236 0.018 Uiso 1 1 calc R C25 C 0.66415(12) 0.1950(3) 0.52783(11) 0.0154(5) Uani 1 1 d . C26 C 0.65670(12) 0.0824(3) 0.56072(12) 0.0174(6) Uani 1 1 d . H26 H 0.6607 -0.0080 0.5474 0.021 Uiso 1 1 calc R C27 C 0.64345(11) 0.1039(3) 0.61317(11) 0.0150(5) Uani 1 1 d . H27 H 0.6381 0.0275 0.6360 0.018 Uiso 1 1 calc R Cl1B Cl 0.27626(3) 0.62069(9) 1.03171(3) 0.0323(2) Uani 1 1 d . S1B S 0.33860(3) 0.42232(7) 0.71425(3) 0.01654(15) Uani 1 1 d . O1B O 0.40742(8) 0.66205(19) 0.81776(8) 0.0159(4) Uani 1 1 d . N1B N 0.43338(10) 0.8500(2) 0.77893(10) 0.0166(5) Uani 1 1 d . H1BA H 0.4684 0.8064 0.7894 0.020 Uiso 1 1 d GR H1BB H 0.4284 0.8892 0.7440 0.020 Uiso 1 1 d GR N2B N 0.30336(10) 0.9728(3) 0.66777(11) 0.0227(5) Uani 1 1 d . N3B N 0.40551(9) 0.4288(2) 0.82443(9) 0.0135(5) Uani 1 1 d . N4B N 0.44211(10) 0.2770(2) 0.77237(10) 0.0174(5) Uani 1 1 d . C1B C 0.38851(12) 0.7605(3) 0.77572(11) 0.0135(5) Uani 1 1 d . C2B C 0.33127(11) 0.7659(3) 0.73845(11) 0.0137(5) Uani 1 1 d . C3B C 0.28377(11) 0.6625(3) 0.74155(11) 0.0135(5) Uani 1 1 d . H3B H 0.2628 0.6996 0.7695 0.016 Uiso 1 1 calc R C4B C 0.31401(11) 0.5273(3) 0.76758(11) 0.0143(5) Uani 1 1 d . H4B H 0.2839 0.4724 0.7804 0.017 Uiso 1 1 calc R C5B C 0.36910(12) 0.5492(3) 0.82259(11) 0.0143(5) Uani 1 1 d . C6B C 0.39957(12) 0.3643(3) 0.77142(11) 0.0150(5) Uani 1 1 d . C7B C 0.48192(12) 0.2887(3) 0.83022(12) 0.0174(6) Uani 1 1 d . C8B C 0.46076(11) 0.3857(3) 0.86282(11) 0.0148(5) Uani 1 1 d . C9B C 0.53651(13) 0.2231(3) 0.85592(13) 0.0216(6) Uani 1 1 d . H9B H 0.5514 0.1562 0.8347 0.026 Uiso 1 1 calc R C10B C 0.56815(13) 0.2584(3) 0.91307(13) 0.0232(6) Uani 1 1 d . H10B H 0.6056 0.2148 0.9314 0.028 Uiso 1 1 calc R C11B C 0.54685(13) 0.3565(3) 0.94495(13) 0.0220(6) Uani 1 1 d . H11B H 0.5701 0.3784 0.9843 0.026 Uiso 1 1 calc R C12B C 0.49239(12) 0.4225(3) 0.92026(12) 0.0194(6) Uani 1 1 d . H12B H 0.4776 0.4892 0.9416 0.023 Uiso 1 1 calc R C13B C 0.31589(11) 0.8791(3) 0.69893(12) 0.0151(6) Uani 1 1 d . C14B C 0.23616(12) 0.6353(3) 0.68268(12) 0.0155(5) Uani 1 1 d . C15B C 0.25004(12) 0.6347(3) 0.62959(12) 0.0172(6) Uani 1 1 d . H15B H 0.2897 0.6565 0.6294 0.021 Uiso 1 1 calc R C16B C 0.20643(13) 0.6025(3) 0.57674(12) 0.0198(6) Uani 1 1 d . H16B H 0.2168 0.6020 0.5409 0.024 Uiso 1 1 calc R C17B C 0.14775(13) 0.5710(3) 0.57547(13) 0.0207(6) Uani 1 1 d . C18B C 0.13408(12) 0.5725(3) 0.62903(13) 0.0198(6) Uani 1 1 d . H18B H 0.0944 0.5509 0.6293 0.024 Uiso 1 1 calc R C19B C 0.17732(12) 0.6050(3) 0.68170(12) 0.0172(6) Uani 1 1 d . H19B H 0.1669 0.6066 0.7175 0.021 Uiso 1 1 calc R C20B C 0.10058(14) 0.5361(3) 0.51782(14) 0.0274(7) Uani 1 1 d . H20C H 0.0838 0.4442 0.5213 0.033 Uiso 1 1 calc R H20D H 0.1197 0.5320 0.4858 0.033 Uiso 1 1 calc R C21B C 0.04963(15) 0.6401(4) 0.50137(16) 0.0385(9) Uani 1 1 d . H21D H 0.0210 0.6151 0.4631 0.058 Uiso 1 1 calc GR H21E H 0.0660 0.7315 0.4985 0.058 Uiso 1 1 calc GR H21F H 0.0290 0.6407 0.5319 0.058 Uiso 1 1 calc GR C22B C 0.34959(11) 0.5680(3) 0.87764(11) 0.0125(5) Uani 1 1 d . C23B C 0.33424(12) 0.6981(3) 0.89265(12) 0.0184(6) Uani 1 1 d . H23B H 0.3399 0.7760 0.8708 0.022 Uiso 1 1 calc R C24B C 0.31061(12) 0.7141(3) 0.93960(13) 0.0206(6) Uani 1 1 d . H24B H 0.2994 0.8024 0.9496 0.025 Uiso 1 1 calc R C25B C 0.30371(12) 0.6001(3) 0.97144(12) 0.0195(6) Uani 1 1 d . C26B C 0.31889(12) 0.4702(3) 0.95752(12) 0.0173(6) Uani 1 1 d . H26B H 0.3140 0.3929 0.9801 0.021 Uiso 1 1 calc R C27B C 0.34144(11) 0.4549(3) 0.90984(11) 0.0146(5) Uani 1 1 d . H27B H 0.3514 0.3660 0.8992 0.017 Uiso 1 1 calc R O1S O 0.45121(8) 0.0598(2) 0.70094(8) 0.0185(4) Uani 1 1 d . H1S H 0.4472 0.1327 0.7190 0.028 Uiso 1 1 d R C2S C 0.42631(16) 0.0904(4) 0.63926(14) 0.0356(8) Uani 1 1 d . H2SA H 0.4227 0.0056 0.6162 0.053 Uiso 1 1 calc GR H2SB H 0.4527 0.1547 0.6272 0.053 Uiso 1 1 calc GR H2SC H 0.3865 0.1317 0.6322 0.053 Uiso 1 1 calc GR O5S O 0.55964(9) 0.7432(2) 0.82672(8) 0.0213(4) Uani 1 1 d . H5S H 0.5572 0.6796 0.8022 0.032 Uiso 1 1 calc GR C6S C 0.5965(2) 0.7002(5) 0.88369(16) 0.0535(11) Uani 1 1 d . H6SA H 0.6336 0.6594 0.8801 0.080 Uiso 1 1 calc GR H6SB H 0.5747 0.6322 0.8999 0.080 Uiso 1 1 calc GR H6SC H 0.6064 0.7796 0.9103 0.080 Uiso 1 1 calc GR loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0285(4) 0.0267(4) 0.0171(3) 0.0043(3) 0.0135(3) 0.0097(3) S1 0.0204(3) 0.0166(4) 0.0140(3) -0.0028(2) 0.0045(3) 0.0030(3) O1 0.0124(9) 0.0159(10) 0.0145(9) 0.0031(7) 0.0048(7) -0.0011(7) N1 0.0111(11) 0.0147(13) 0.0203(12) 0.0031(9) 0.0038(9) -0.0027(8) N2 0.0222(14) 0.0234(16) 0.0367(16) 0.0117(12) 0.0009(12) -0.0019(11) N3 0.0129(11) 0.0137(12) 0.0156(11) -0.0018(8) 0.0049(9) 0.0011(9) N4 0.0222(12) 0.0149(13) 0.0197(12) 0.0002(9) 0.0113(10) 0.0034(9) C1 0.0178(14) 0.0115(14) 0.0138(13) -0.0022(10) 0.0089(11) 0.0019(10) C2 0.0155(13) 0.0123(14) 0.0165(13) -0.0003(10) 0.0070(11) -0.0007(10) C3 0.0128(13) 0.0122(14) 0.0142(13) -0.0019(10) 0.0051(11) 0.0003(10) C4 0.0169(14) 0.0121(14) 0.0148(13) -0.0033(10) 0.0082(11) -0.0008(10) C5 0.0149(13) 0.0090(14) 0.0178(13) 0.0005(10) 0.0071(11) 0.0012(10) C6 0.0193(14) 0.0126(15) 0.0172(14) 0.0006(10) 0.0074(11) 0.0001(10) C7 0.0195(14) 0.0164(15) 0.0205(14) 0.0024(11) 0.0105(12) 0.0006(11) C8 0.0129(13) 0.0149(15) 0.0232(15) 0.0034(11) 0.0092(11) 0.0030(10) C9 0.0233(15) 0.0197(17) 0.0329(17) 0.0027(12) 0.0172(13) 0.0075(12) C10 0.0171(15) 0.0303(19) 0.0329(18) 0.0075(13) 0.0073(13) 0.0103(12) C11 0.0221(16) 0.0261(18) 0.0239(16) 0.0048(12) 0.0030(13) 0.0053(12) C12 0.0174(14) 0.0203(16) 0.0224(15) -0.0006(11) 0.0067(12) 0.0024(11) C13 0.0116(13) 0.0186(16) 0.0239(15) -0.0003(12) 0.0041(11) -0.0029(10) C14 0.0148(13) 0.0088(14) 0.0160(13) -0.0011(10) 0.0040(11) 0.0018(10) C15 0.0173(14) 0.0112(14) 0.0166(13) 0.0002(10) 0.0067(11) 0.0018(10) C16 0.0221(14) 0.0102(14) 0.0158(13) -0.0009(10) 0.0068(11) 0.0031(10) C17 0.0160(14) 0.0103(15) 0.0211(14) -0.0010(10) 0.0022(11) 0.0011(10) C18 0.0143(13) 0.0141(15) 0.0237(15) 0.0001(11) 0.0078(12) -0.0002(10) C19 0.0177(14) 0.0118(14) 0.0152(13) 0.0023(10) 0.0057(11) 0.0019(10) C20 0.0180(15) 0.0269(18) 0.0257(16) -0.0055(12) -0.0003(13) 0.0024(12) C21 0.0174(15) 0.034(2) 0.0343(18) -0.0101(14) -0.0032(13) -0.0042(13) C22 0.0102(12) 0.0150(15) 0.0111(13) -0.0010(10) 0.0025(10) -0.0003(10) C23 0.0133(13) 0.0139(15) 0.0155(13) -0.0002(10) 0.0040(11) 0.0009(10) C24 0.0147(13) 0.0168(15) 0.0132(13) 0.0035(10) 0.0027(11) -0.0001(10) C25 0.0143(13) 0.0201(16) 0.0128(13) 0.0004(10) 0.0056(11) 0.0043(10) C26 0.0210(14) 0.0146(15) 0.0183(14) -0.0027(10) 0.0084(12) 0.0035(11) C27 0.0160(13) 0.0132(15) 0.0166(14) 0.0016(10) 0.0062(11) 0.0004(10) Cl1B 0.0341(4) 0.0395(5) 0.0337(4) -0.0188(3) 0.0259(4) -0.0130(3) S1B 0.0194(3) 0.0166(4) 0.0137(3) -0.0017(2) 0.0051(3) 0.0017(3) O1B 0.0126(9) 0.0162(11) 0.0175(10) 0.0055(7) 0.0026(8) -0.0018(7) N1B 0.0154(11) 0.0160(13) 0.0195(12) 0.0026(9) 0.0071(10) -0.0001(9) N2B 0.0189(13) 0.0226(15) 0.0261(13) 0.0064(11) 0.0060(11) 0.0013(10) N3B 0.0145(11) 0.0140(12) 0.0137(11) -0.0001(8) 0.0067(9) 0.0020(8) N4B 0.0207(12) 0.0165(13) 0.0163(12) -0.0012(9) 0.0077(10) 0.0011(9) C1B 0.0158(13) 0.0110(14) 0.0167(13) -0.0023(10) 0.0093(11) -0.0002(10) C2B 0.0148(13) 0.0129(15) 0.0153(13) 0.0014(10) 0.0073(11) 0.0003(10) C3B 0.0131(13) 0.0145(15) 0.0143(13) -0.0002(10) 0.0061(11) 0.0004(10) C4B 0.0149(13) 0.0142(15) 0.0163(13) -0.0005(10) 0.0084(11) -0.0018(10) C5B 0.0161(13) 0.0119(15) 0.0164(13) 0.0013(10) 0.0071(11) -0.0007(10) C6B 0.0174(14) 0.0140(15) 0.0164(13) 0.0009(10) 0.0092(11) -0.0021(10) C7B 0.0195(14) 0.0174(16) 0.0180(14) 0.0000(11) 0.0095(12) -0.0006(11) C8B 0.0143(13) 0.0156(15) 0.0168(13) 0.0034(10) 0.0083(11) 0.0019(10) C9B 0.0214(15) 0.0202(17) 0.0275(16) 0.0012(12) 0.0136(13) 0.0067(11) C10B 0.0194(15) 0.0228(17) 0.0283(16) 0.0045(12) 0.0084(13) 0.0055(12) C11B 0.0183(15) 0.0261(18) 0.0210(15) 0.0004(11) 0.0049(12) -0.0002(11) C12B 0.0196(14) 0.0226(16) 0.0181(14) 0.0008(11) 0.0089(12) 0.0038(11) C13B 0.0090(12) 0.0186(16) 0.0185(14) -0.0027(11) 0.0053(11) -0.0013(10) C14B 0.0167(14) 0.0104(14) 0.0194(14) 0.0022(10) 0.0057(11) 0.0022(10) C15B 0.0179(14) 0.0142(15) 0.0200(14) -0.0002(10) 0.0064(11) 0.0005(10) C16B 0.0253(15) 0.0145(16) 0.0208(15) -0.0025(11) 0.0087(12) 0.0012(11) C17B 0.0219(15) 0.0125(15) 0.0243(15) -0.0031(11) 0.0017(12) 0.0017(11) C18B 0.0144(14) 0.0140(15) 0.0299(16) 0.0005(11) 0.0049(12) -0.0009(10) C19B 0.0172(14) 0.0135(15) 0.0225(15) 0.0020(11) 0.0083(12) 0.0009(10) C20B 0.0255(16) 0.0215(18) 0.0306(17) -0.0069(12) 0.0015(14) 0.0000(12) C21B 0.0299(19) 0.036(2) 0.039(2) -0.0080(15) -0.0062(16) 0.0056(15) C22B 0.0090(12) 0.0143(14) 0.0132(13) -0.0033(10) 0.0022(10) 0.0003(9) C23B 0.0190(14) 0.0161(16) 0.0208(14) -0.0012(11) 0.0074(12) -0.0001(11) C24B 0.0166(14) 0.0206(17) 0.0251(15) -0.0100(11) 0.0073(12) 0.0007(11) C25B 0.0143(13) 0.0271(17) 0.0206(14) -0.0107(11) 0.0105(12) -0.0071(11) C26B 0.0181(14) 0.0201(16) 0.0154(13) -0.0039(10) 0.0077(11) -0.0056(11) C27B 0.0120(13) 0.0146(15) 0.0173(13) -0.0033(10) 0.0047(11) -0.0016(10) O1S 0.0199(10) 0.0146(11) 0.0231(10) -0.0008(7) 0.0098(8) 0.0003(7) C2S 0.0357(19) 0.047(2) 0.0267(18) 0.0009(15) 0.0131(15) -0.0082(16) O5S 0.0242(11) 0.0202(12) 0.0213(10) -0.0006(8) 0.0094(9) -0.0013(8) C6S 0.068(3) 0.060(3) 0.032(2) 0.0034(18) 0.014(2) -0.018(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' Cl Cl 0.3639 0.7018 '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 C6 S1 C4 89.47(12) C1 O1 C5 121.9(2) H1A N1 H1B 106.6 C1 N1 H1A 123.8 C1 N1 H1B 126.5 C6 N3 C5 115.4(2) C6 N3 C8 106.6(2) C8 N3 C5 133.6(2) C6 N4 C7 103.9(2) O1 C1 C2 122.8(2) N1 C1 O1 109.5(2) N1 C1 C2 127.6(2) C1 C2 C3 120.9(2) C1 C2 C13 116.8(2) C13 C2 C3 122.1(2) C2 C3 H3 107.2 C2 C3 C4 108.8(2) C2 C3 C14 115.4(2) C4 C3 H3 107.2 C14 C3 H3 107.2 C14 C3 C4 110.8(2) S1 C4 H4 108.1 C3 C4 S1 113.80(17) C3 C4 H4 108.1 C5 C4 S1 106.69(17) C5 C4 C3 112.0(2) C5 C4 H4 108.1 O1 C5 C4 113.2(2) O1 C5 C22 108.9(2) N3 C5 O1 105.11(19) N3 C5 C4 104.0(2) N3 C5 C22 113.6(2) C22 C5 C4 111.8(2) N3 C6 S1 113.32(19) N4 C6 S1 132.5(2) N4 C6 N3 114.2(2) C8 C7 N4 110.6(2) C9 C7 N4 129.1(3) C9 C7 C8 120.3(3) N3 C8 C7 104.6(2) C12 C8 N3 132.9(2) C12 C8 C7 122.5(2) C7 C9 H9 121.2 C10 C9 C7 117.6(3) C10 C9 H9 121.2 C9 C10 H10 119.1 C9 C10 C11 121.8(3) C11 C10 H10 119.1 C10 C11 H11 119.2 C10 C11 C12 121.6(3) C12 C11 H11 119.2 C8 C12 C11 116.2(3) C8 C12 H12 121.9 C11 C12 H12 121.9 N2 C13 C2 177.9(3) C15 C14 C3 123.2(2) C15 C14 C19 118.2(2) C19 C14 C3 118.6(2) C14 C15 H15 119.9 C16 C15 C14 120.3(2) C16 C15 H15 119.9 C15 C16 H16 119.1 C15 C16 C17 121.8(2) C17 C16 H16 119.1 C16 C17 C20 120.4(2) C18 C17 C16 117.6(2) C18 C17 C20 122.0(2) C17 C18 H18 119.5 C19 C18 C17 121.1(2) C19 C18 H18 119.5 C14 C19 H19 119.5 C18 C19 C14 121.0(2) C18 C19 H19 119.5 C17 C20 H20A 108.3 C17 C20 H20B 108.3 C17 C20 C21 115.7(3) H20A C20 H20B 107.4 C21 C20 H20A 108.3 C21 C20 H20B 108.3 C20 C21 H21A 109.5 C20 C21 H21B 109.5 C20 C21 H21C 109.5 H21A C21 H21B 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C23 C22 C5 119.4(2) C27 C22 C5 120.8(2) C27 C22 C23 119.6(2) C22 C23 H23 119.9 C24 C23 C22 120.1(2) C24 C23 H23 119.9 C23 C24 H24 120.4 C25 C24 C23 119.1(2) C25 C24 H24 120.4 C24 C25 Cl1 120.0(2) C24 C25 C26 121.5(2) C26 C25 Cl1 118.5(2) C25 C26 H26 120.5 C27 C26 C25 118.9(3) C27 C26 H26 120.5 C22 C27 H27 119.7 C26 C27 C22 120.7(2) C26 C27 H27 119.7 C6B S1B C4B 89.86(12) C1B O1B C5B 121.6(2) H1BA N1B H1BB 108.7 C1B N1B H1BA 109.8 C1B N1B H1BB 110.1 C6B N3B C5B 116.7(2) C6B N3B C8B 106.0(2) C8B N3B C5B 133.1(2) C6B N4B C7B 103.9(2) O1B C1B C2B 122.8(2) N1B C1B O1B 109.9(2) N1B C1B C2B 127.2(3) C1B C2B C3B 122.1(2) C1B C2B C13B 117.4(2) C13B C2B C3B 120.3(2) C2B C3B H3B 107.5 C2B C3B C4B 109.6(2) C2B C3B C14B 114.5(2) C4B C3B H3B 107.5 C14B C3B H3B 107.5 C14B C3B C4B 109.8(2) S1B C4B H4B 107.5 C3B C4B S1B 113.67(17) C3B C4B H4B 107.5 C3B C4B C5B 112.7(2) C5B C4B S1B 107.61(17) C5B C4B H4B 107.5 O1B C5B C4B 114.6(2) O1B C5B C22B 109.2(2) N3B C5B O1B 104.5(2) N3B C5B C4B 104.3(2) N3B C5B C22B 113.5(2) C22B C5B C4B 110.7(2) N3B C6B S1B 113.39(19) N4B C6B S1B 131.9(2) N4B C6B N3B 114.6(2) C8B C7B N4B 110.6(2) C9B C7B N4B 129.6(3) C9B C7B C8B 119.8(3) N3B C8B C7B 104.7(2) C12B C8B N3B 132.4(2) C12B C8B C7B 122.9(2) C7B C9B H9B 121.1 C10B C9B C7B 117.7(3) C10B C9B H9B 121.1 C9B C10B H10B 119.0 C9B C10B C11B 121.9(3) C11B C10B H10B 119.0 C10B C11B H11B 119.4 C12B C11B C10B 121.2(3) C12B C11B H11B 119.4 C8B C12B C11B 116.4(3) C8B C12B H12B 121.8 C11B C12B H12B 121.8 N2B C13B C2B 178.6(3) C15B C14B C3B 121.7(2) C15B C14B C19B 118.6(3) C19B C14B C3B 119.7(2) C14B C15B H15B 119.7 C14B C15B C16B 120.6(3) C16B C15B H15B 119.7 C15B C16B H16B 119.4 C15B C16B C17B 121.2(3) C17B C16B H16B 119.4 C16B C17B C18B 117.9(3) C16B C17B C20B 120.8(3) C18B C17B C20B 121.3(3) C17B C18B H18B 119.4 C19B C18B C17B 121.1(3) C19B C18B H18B 119.4 C14B C19B H19B 119.7 C18B C19B C14B 120.6(3) C18B C19B H19B 119.7 C17B C20B H20C 109.1 C17B C20B H20D 109.1 C17B C20B C21B 112.4(3) H20C C20B H20D 107.8 C21B C20B H20C 109.1 C21B C20B H20D 109.1 C20B C21B H21D 109.5 C20B C21B H21E 109.5 C20B C21B H21F 109.5 H21D C21B H21E 109.5 H21D C21B H21F 109.5 H21E C21B H21F 109.5 C23B C22B C5B 119.8(2) C27B C22B C5B 120.2(2) C27B C22B C23B 119.7(2) C22B C23B H23B 120.0 C24B C23B C22B 120.0(3) C24B C23B H23B 120.0 C23B C24B H24B 120.5 C25B C24B C23B 119.1(3) C25B C24B H24B 120.5 C24B C25B Cl1B 119.1(2) C24B C25B C26B 121.9(2) C26B C25B Cl1B 119.0(2) C25B C26B H26B 120.7 C25B C26B C27B 118.6(3) C27B C26B H26B 120.7 C22B C27B C26B 120.6(2) C22B C27B H27B 119.7 C26B C27B H27B 119.7 C2S O1S H1S 105.5 O1S C2S H2SA 109.5 O1S C2S H2SB 109.5 O1S C2S H2SC 109.5 H2SA C2S H2SB 109.5 H2SA C2S H2SC 109.5 H2SB C2S H2SC 109.5 C6S O5S H5S 109.5 O5S C6S H6SA 109.5 O5S C6S H6SB 109.5 O5S C6S H6SC 109.5 H6SA C6S H6SB 109.5 H6SA C6S H6SC 109.5 H6SB C6S H6SC 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C25 1.741(3) S1 C4 1.849(3) S1 C6 1.738(3) O1 C1 1.359(3) O1 C5 1.449(3) N1 H1A 0.8870 N1 H1B 0.8869 N1 C1 1.337(3) N2 C13 1.154(4) N3 C5 1.441(3) N3 C6 1.375(3) N3 C8 1.392(3) N4 C6 1.305(3) N4 C7 1.410(4) C1 C2 1.363(4) C2 C3 1.516(3) C2 C13 1.412(4) C3 H3 1.0000 C3 C4 1.535(4) C3 C14 1.525(4) C4 H4 1.0000 C4 C5 1.535(4) C5 C22 1.513(3) C7 C8 1.403(4) C7 C9 1.391(4) C8 C12 1.387(4) C9 H9 0.9500 C9 C10 1.379(4) C10 H10 0.9500 C10 C11 1.393(4) C11 H11 0.9500 C11 C12 1.395(4) C12 H12 0.9500 C14 C15 1.394(4) C14 C19 1.396(4) C15 H15 0.9500 C15 C16 1.390(4) C16 H16 0.9500 C16 C17 1.395(4) C17 C18 1.392(4) C17 C20 1.516(4) C18 H18 0.9500 C18 C19 1.390(4) C19 H19 0.9500 C20 H20A 0.9900 C20 H20B 0.9900 C20 C21 1.529(4) C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 C22 C23 1.396(4) C22 C27 1.385(4) C23 H23 0.9500 C23 C24 1.387(4) C24 H24 0.9500 C24 C25 1.380(4) C25 C26 1.386(4) C26 H26 0.9500 C26 C27 1.383(4) C27 H27 0.9500 Cl1B C25B 1.742(3) S1B C4B 1.845(3) S1B C6B 1.737(3) O1B C1B 1.357(3) O1B C5B 1.444(3) N1B H1BA 0.8871 N1B H1BB 0.8868 N1B C1B 1.347(3) N2B C13B 1.155(4) N3B C5B 1.441(3) N3B C6B 1.373(3) N3B C8B 1.400(3) N4B C6B 1.302(3) N4B C7B 1.410(4) C1B C2B 1.363(4) C2B C3B 1.515(3) C2B C13B 1.422(4) C3B H3B 1.0000 C3B C4B 1.534(4) C3B C14B 1.522(4) C4B H4B 1.0000 C4B C5B 1.545(4) C5B C22B 1.515(3) C7B C8B 1.401(4) C7B C9B 1.391(4) C8B C12B 1.385(4) C9B H9B 0.9500 C9B C10B 1.376(4) C10B H10B 0.9500 C10B C11B 1.399(4) C11B H11B 0.9500 C11B C12B 1.387(4) C12B H12B 0.9500 C14B C15B 1.389(4) C14B C19B 1.397(4) C15B H15B 0.9500 C15B C16B 1.391(4) C16B H16B 0.9500 C16B C17B 1.394(4) C17B C18B 1.397(4) C17B C20B 1.512(4) C18B H18B 0.9500 C18B C19B 1.384(4) C19B H19B 0.9500 C20B H20C 0.9900 C20B H20D 0.9900 C20B C21B 1.521(4) C21B H21D 0.9800 C21B H21E 0.9800 C21B H21F 0.9800 C22B C23B 1.393(4) C22B C27B 1.386(4) C23B H23B 0.9500 C23B C24B 1.389(4) C24B H24B 0.9500 C24B C25B 1.379(4) C25B C26B 1.382(4) C26B H26B 0.9500 C26B C27B 1.389(4) C27B H27B 0.9500 O1S H1S 0.8499 O1S C2S 1.431(4) C2S H2SA 0.9800 C2S H2SB 0.9800 C2S H2SC 0.9800 O5S H5S 0.8400 O5S C6S 1.427(4) C6S H6SA 0.9800 C6S H6SB 0.9800 C6S H6SC 0.9800 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 Cl1 C25 C26 C27 179.8(2) S1 C4 C5 O1 -79.9(2) S1 C4 C5 N3 33.7(2) S1 C4 C5 C22 156.66(18) O1 C1 C2 C3 -0.9(4) O1 C1 C2 C13 -176.6(2) O1 C5 C22 C23 152.0(2) O1 C5 C22 C27 -31.8(3) N1 C1 C2 C3 177.7(2) N1 C1 C2 C13 2.0(4) N3 C5 C22 C23 35.2(3) N3 C5 C22 C27 -148.6(2) N3 C8 C12 C11 -177.4(3) N4 C7 C8 N3 -1.8(3) N4 C7 C8 C12 179.8(2) N4 C7 C9 C10 180.0(3) C1 O1 C5 N3 -129.2(2) C1 O1 C5 C4 -16.3(3) C1 O1 C5 C22 108.7(2) C1 C2 C3 C4 29.7(3) C1 C2 C3 C14 154.9(2) C2 C3 C4 S1 70.9(2) C2 C3 C4 C5 -50.2(3) C2 C3 C14 C15 -36.4(3) C2 C3 C14 C19 145.7(2) C3 C4 C5 O1 45.2(3) C3 C4 C5 N3 158.8(2) C3 C4 C5 C22 -78.2(3) C3 C14 C15 C16 -178.1(2) C3 C14 C19 C18 178.3(2) C4 S1 C6 N3 6.5(2) C4 S1 C6 N4 -176.2(3) C4 C3 C14 C15 87.7(3) C4 C3 C14 C19 -90.2(3) C4 C5 C22 C23 -82.2(3) C4 C5 C22 C27 94.1(3) C5 O1 C1 N1 174.4(2) C5 O1 C1 C2 -6.7(4) C5 N3 C6 S1 14.5(3) C5 N3 C6 N4 -163.3(2) C5 N3 C8 C7 157.4(3) C5 N3 C8 C12 -24.5(5) C5 C22 C23 C24 176.6(2) C5 C22 C27 C26 -176.4(2) C6 S1 C4 C3 -147.5(2) C6 S1 C4 C5 -23.50(19) C6 N3 C5 O1 87.7(3) C6 N3 C5 C4 -31.6(3) C6 N3 C5 C22 -153.3(2) C6 N3 C8 C7 3.1(3) C6 N3 C8 C12 -178.8(3) C6 N4 C7 C8 -0.3(3) C6 N4 C7 C9 -179.8(3) C7 N4 C6 S1 -174.9(2) C7 N4 C6 N3 2.4(3) C7 C8 C12 C11 0.4(4) C7 C9 C10 C11 -0.3(5) C8 N3 C5 O1 -64.9(3) C8 N3 C5 C4 175.8(3) C8 N3 C5 C22 54.0(4) C8 N3 C6 S1 174.17(18) C8 N3 C6 N4 -3.6(3) C8 C7 C9 C10 0.5(4) C9 C7 C8 N3 177.7(2) C9 C7 C8 C12 -0.6(4) C9 C10 C11 C12 0.1(5) C10 C11 C12 C8 -0.1(4) C13 C2 C3 C4 -154.8(2) C13 C2 C3 C14 -29.6(3) C14 C3 C4 S1 -57.0(2) C14 C3 C4 C5 -178.1(2) C14 C15 C16 C17 -0.2(4) C15 C14 C19 C18 0.3(4) C15 C16 C17 C18 0.6(4) C15 C16 C17 C20 -177.2(3) C16 C17 C18 C19 -0.6(4) C16 C17 C20 C21 -148.0(3) C17 C18 C19 C14 0.1(4) C18 C17 C20 C21 34.3(4) C19 C14 C15 C16 -0.3(4) C20 C17 C18 C19 177.2(3) C22 C23 C24 C25 0.0(4) C23 C22 C27 C26 -0.2(4) C23 C24 C25 Cl1 -179.7(2) C23 C24 C25 C26 -0.4(4) C24 C25 C26 C27 0.6(4) C25 C26 C27 C22 -0.2(4) C27 C22 C23 C24 0.4(4) Cl1B C25B C26B C27B -179.2(2) S1B C4B C5B O1B 84.4(2) S1B C4B C5B N3B -29.1(2) S1B C4B C5B C22B -151.57(18) O1B C1B C2B C3B 0.7(4) O1B C1B C2B C13B 175.9(2) O1B C5B C22B C23B 40.4(3) O1B C5B C22B C27B -145.8(2) N1B C1B C2B C3B -176.5(2) N1B C1B C2B C13B -1.3(4) N3B C5B C22B C23B 156.5(2) N3B C5B C22B C27B -29.7(3) N3B C8B C12B C11B 179.8(3) N4B C7B C8B N3B 2.6(3) N4B C7B C8B C12B -177.0(2) N4B C7B C9B C10B 176.9(3) C1B O1B C5B N3B 129.6(2) C1B O1B C5B C4B 16.1(3) C1B O1B C5B C22B -108.7(2) C1B C2B C3B C4B -26.4(3) C1B C2B C3B C14B -150.3(2) C2B C3B C4B S1B -77.9(2) C2B C3B C4B C5B 44.9(3) C2B C3B C14B C15B 35.4(3) C2B C3B C14B C19B -147.0(2) C3B C4B C5B O1B -41.7(3) C3B C4B C5B N3B -155.3(2) C3B C4B C5B C22B 82.3(3) C3B C14B C15B C16B 176.6(3) C3B C14B C19B C18B -176.5(2) C4B S1B C6B N3B -6.7(2) C4B S1B C6B N4B 177.7(3) C4B C3B C14B C15B -88.4(3) C4B C3B C14B C19B 89.2(3) C4B C5B C22B C23B -86.7(3) C4B C5B C22B C27B 87.1(3) C5B O1B C1B N1B -177.2(2) C5B O1B C1B C2B 5.2(4) C5B N3B C6B S1B -11.5(3) C5B N3B C6B N4B 164.9(2) C5B N3B C8B C7B -159.5(3) C5B N3B C8B C12B 20.0(5) C5B C22B C23B C24B 173.6(2) C5B C22B C27B C26B -174.7(2) C6B S1B C4B C3B 146.5(2) C6B S1B C4B C5B 20.99(19) C6B N3B C5B O1B -94.0(2) C6B N3B C5B C4B 26.6(3) C6B N3B C5B C22B 147.2(2) C6B N3B C8B C7B -4.3(3) C6B N3B C8B C12B 175.3(3) C6B N4B C7B C8B 0.2(3) C6B N4B C7B C9B -177.6(3) C7B N4B C6B S1B 172.4(2) C7B N4B C6B N3B -3.2(3) C7B C8B C12B C11B -0.7(4) C7B C9B C10B C11B 0.1(4) C8B N3B C5B O1B 59.3(3) C8B N3B C5B C4B 179.9(2) C8B N3B C5B C22B -59.6(4) C8B N3B C6B S1B -171.50(18) C8B N3B C6B N4B 4.9(3) C8B C7B C9B C10B -0.7(4) C9B C7B C8B N3B -179.3(2) C9B C7B C8B C12B 1.1(4) C9B C10B C11B C12B 0.3(5) C10B C11B C12B C8B 0.0(4) C13B C2B C3B C4B 158.5(2) C13B C2B C3B C14B 34.6(3) C14B C3B C4B S1B 48.7(2) C14B C3B C4B C5B 171.5(2) C14B C15B C16B C17B 0.4(4) C15B C14B C19B C18B 1.2(4) C15B C16B C17B C18B -0.1(4) C15B C16B C17B C20B 180.0(3) C16B C17B C18B C19B 0.3(4) C16B C17B C20B C21B -116.1(3) C17B C18B C19B C14B -0.9(4) C18B C17B C20B C21B 64.0(4) C19B C14B C15B C16B -1.0(4) C20B C17B C18B C19B -179.8(3) C22B C23B C24B C25B 1.1(4) C23B C22B C27B C26B -0.9(4) C23B C24B C25B Cl1B 178.0(2) C23B C24B C25B C26B -0.8(4) C24B C25B C26B C27B -0.3(4) C25B C26B C27B C22B 1.2(4) C27B C22B C23B C24B -0.3(4)