#------------------------------------------------------------------------------ #$Date: 2022-01-07 01:33:21 +0200 (Fri, 07 Jan 2022) $ #$Revision: 271921 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243912.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2243912 loop_ _publ_author_name 'Fujii, Isao' _publ_section_title ; Crystal structure of nafamostat dimesylate ; _journal_coeditor_code TX2042 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 999 _journal_page_last 1002 _journal_paper_doi 10.1107/S2056989021009245 _journal_volume 77 _journal_year 2021 _chemical_compound_source 'see text' _chemical_formula_iupac 'C19 H19 N5 O2 2+, 2C H3 O3 S -' _chemical_formula_moiety 'C19 H19 N5 O2, 2(C H3 O3 S)' _chemical_formula_sum 'C21 H25 N5 O8 S2' _chemical_formula_weight 539.58 _chemical_name_systematic '[Amino({6-[(4-{[amino(iminiumyl)methyl]amino}phenyl)carbonyloxy]naphthalen-2-yl})methylidene]azanium bis(methanesulfonate)' _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary dual _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4.5 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 96.7460(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.06310(10) _cell_length_b 9.72150(10) _cell_length_c 21.9271(3) _cell_measurement_reflns_used 17552 _cell_measurement_temperature 95(2) _cell_measurement_theta_max 73.45 _cell_measurement_theta_min 4.96 _cell_volume 2341.93(5) _computing_cell_refinement ; Crysalis PRO (Rigaku, 2015) ; _computing_data_collection ; Crysalis PRO (Rigaku, 2015) ; _computing_data_reduction ; SORTAV (Blessing, 1995) ; _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2020) ; _computing_publication_material ; Platon (Spek, 2020), WinGX (Farrugia, 2012) and publCIF (Westrip, 2010) ; _computing_structure_refinement ; SHELXL (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 95(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device 'quarter \C-circle diffractometer' _diffrn_measurement_device_type 'a Rigaku XtaLAB P200 diffractometer' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_unetI/netI 0.0499 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4675 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.836 _diffrn_reflns_theta_min 4.024 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.586 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.46 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku, 2015) ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.53 _exptl_crystal_density_method 'not measured' _exptl_crystal_description octahedron _exptl_crystal_F_000 1128 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.636 _refine_diff_density_min -0.518 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 363 _refine_ls_number_reflns 4675 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.07 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0545 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+4.9921P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1249 _refine_ls_wR_factor_ref 0.1259 _reflns_number_gt 4457 _reflns_number_total 4675 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL shelxt_a.res in P2(1)/c shelx.res created by SHELXL-2018/3 at 17:43:49 on 27-Jul-2021 CELL 1.54184 11.0631 9.7215 21.9271 90.000 96.746 90.000 ZERR 4.00 0.0001 0.0001 0.0003 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 84 100 20 32 8 MERG 2 EQIV $1 -x+1, y-1/2, -z+3/2 HTAB C18 O13_$1 EQIV $2 x, y+1, z HTAB C30 O36_$2 EQIV $3 x-1, -y+3/2, z-1/2 HTAB N22 O31_$3 EQIV $4 -x+2, y-1/2, -z+3/2 HTAB N25 O29_$4 EQIV $5 -x, -y+1, -z+1 HTAB N22 O33_$5 HTAB N25 O28 HTAB N25 S27 EQIV $6 x, y-1, z HTAB N26 O29_$6 HTAB N26 O36 HTAB N15 O33_$5 HTAB N15 O34_$5 HTAB N15 S32_$5 HTAB N26 O31_$4 HTAB N26 S27_$4 EQIV $7 x-1, y+1, z HTAB N15 O34_$7 HTAB N23 O36 HTAB N23 S32 FMAP 2 PLAN 20 SIZE 0.100 0.300 0.400 ACTA BOND BOND $H LIST 4 L.S. 10 TEMP -178.00 WGHT 0.032400 4.992100 FVAR 2.41663 C1 1 0.142234 0.558318 0.565228 11.00000 0.01362 0.01823 = 0.03414 -0.00117 -0.00295 0.00169 C2 1 0.058034 0.589235 0.606203 11.00000 0.01628 0.02406 = 0.03066 0.00184 0.00234 -0.00098 AFIX 43 H2 2 0.061778 0.544066 0.644799 11.00000 -1.20000 AFIX 0 C3 1 -0.030406 0.686495 0.589449 11.00000 0.01336 0.02529 = 0.03238 -0.00280 0.00601 0.00001 AFIX 43 H3 2 -0.086637 0.710328 0.617287 11.00000 -1.20000 AFIX 0 C4 1 -0.038355 0.750466 0.532010 11.00000 0.01295 0.02243 = 0.03192 -0.00348 0.00211 -0.00156 C5 1 -0.124146 0.855007 0.515784 11.00000 0.01411 0.02451 = 0.03055 -0.00298 0.00472 -0.00180 AFIX 43 H5 2 -0.177017 0.883065 0.544597 11.00000 -1.20000 AFIX 0 C6 1 -0.133287 0.918375 0.458313 11.00000 0.01263 0.01944 = 0.03587 -0.00107 0.00021 -0.00085 C7 1 -0.054464 0.876215 0.415621 11.00000 0.01842 0.02503 = 0.02713 0.00115 0.00052 -0.00143 AFIX 43 H7 2 -0.060246 0.917718 0.376162 11.00000 -1.20000 AFIX 0 C8 1 0.030218 0.775638 0.431054 11.00000 0.01601 0.02167 = 0.03013 -0.00306 0.00076 0.00227 AFIX 43 H8 2 0.081746 0.747936 0.401556 11.00000 -1.20000 AFIX 0 C9 1 0.043715 0.711592 0.489260 11.00000 0.01561 0.02485 = 0.02558 -0.00122 0.00148 -0.00385 C10 1 0.135163 0.615110 0.507576 11.00000 0.01775 0.02241 = 0.02773 -0.00122 0.00505 -0.00040 AFIX 43 H10 2 0.191808 0.589251 0.480271 11.00000 -1.20000 AFIX 0 C12 1 0.308011 0.476412 0.634567 11.00000 0.01377 0.01958 = 0.02865 -0.00036 0.00505 -0.00143 C14 1 -0.221405 1.032581 0.444244 11.00000 0.01141 0.01870 = 0.03027 -0.00124 -0.00005 -0.00284 C16 1 0.400549 0.365797 0.643134 11.00000 0.01259 0.02010 = 0.02935 0.00191 0.00334 -0.00133 C17 1 0.475253 0.360013 0.698821 11.00000 0.01696 0.02552 = 0.02435 0.00024 0.00179 -0.00374 AFIX 43 H17 2 0.466534 0.426978 0.729554 11.00000 -1.20000 AFIX 0 C18 1 0.563209 0.256330 0.709978 11.00000 0.01824 0.02194 = 0.02585 -0.00014 0.00004 -0.00154 AFIX 43 H18 2 0.613450 0.252049 0.748167 11.00000 -1.20000 AFIX 0 C19 1 0.575791 0.159931 0.664340 11.00000 0.01437 0.02178 = 0.02905 0.00198 0.00287 -0.00157 C20 1 0.501851 0.165804 0.608195 11.00000 0.01661 0.02503 = 0.02899 0.00085 0.00100 0.00028 AFIX 43 H20 2 0.511470 0.100093 0.577062 11.00000 -1.20000 AFIX 0 C21 1 0.414507 0.267819 0.598141 11.00000 0.02087 0.02173 = 0.02704 -0.00003 0.00687 -0.00207 AFIX 43 H21 2 0.363537 0.271047 0.560152 11.00000 -1.20000 AFIX 0 C24 1 0.775600 0.049941 0.698639 11.00000 0.01419 0.02560 = 0.02474 0.00205 0.00568 0.00263 C30 1 0.710675 0.583250 0.769617 11.00000 0.01508 0.02859 = 0.03008 0.00202 0.00353 0.00511 AFIX 137 H30A 2 0.661242 0.637008 0.738122 11.00000 -1.50000 H30B 2 0.734263 0.641357 0.805571 11.00000 -1.50000 H30C 2 0.663287 0.504665 0.781635 11.00000 -1.50000 AFIX 0 C35 1 0.629254 -0.416742 0.570389 11.00000 0.01943 0.02248 = 0.03593 0.00142 0.00042 0.00229 AFIX 137 H35A 2 0.717501 -0.403331 0.578279 11.00000 -1.50000 H35B 2 0.607172 -0.441466 0.527188 11.00000 -1.50000 H35C 2 0.604676 -0.490755 0.596665 11.00000 -1.50000 AFIX 0 N15 3 -0.303334 1.056545 0.482042 11.00000 0.01692 0.02260 = 0.03244 0.00622 0.00540 0.00373 N22 3 -0.217548 1.112767 0.396418 11.00000 0.01486 0.02170 = 0.02798 0.00038 0.00367 0.00190 N23 3 0.657333 0.047468 0.673773 11.00000 0.01370 0.02453 = 0.03338 -0.00012 -0.00119 0.00274 N25 3 0.836476 0.163144 0.710944 11.00000 0.01604 0.01873 = 0.03783 0.00349 0.00367 0.00279 N26 3 0.828349 -0.071775 0.708247 11.00000 0.01458 0.02021 = 0.04086 0.00051 0.00343 0.00140 O11 4 0.233873 0.461894 0.579933 11.00000 0.01421 0.02379 = 0.02667 -0.00278 0.00023 0.00215 O13 4 0.296559 0.568436 0.670191 11.00000 0.01836 0.02703 = 0.03099 -0.00234 0.00188 0.00288 O28 4 0.801549 0.446022 0.684744 11.00000 0.02340 0.02019 = 0.02640 -0.00098 0.00214 0.00130 O29 4 0.913269 0.645117 0.728541 11.00000 0.02025 0.02004 = 0.03579 0.00365 0.00588 -0.00045 O31 4 0.907335 0.436034 0.787857 11.00000 0.01358 0.02362 = 0.02884 0.00596 0.00120 0.00450 O33 4 0.425060 -0.292123 0.573309 11.00000 0.01264 0.02484 = 0.05469 0.00658 0.00268 0.00061 O34 4 0.591930 -0.157244 0.545954 11.00000 0.02879 0.02143 = 0.03575 0.00670 0.01016 0.00047 O36 4 0.591905 -0.231381 0.650572 11.00000 0.03980 0.02255 = 0.02819 0.00130 -0.00382 0.00105 S27 5 0.842515 0.523337 0.739953 11.00000 0.01241 0.01842 = 0.02636 0.00185 0.00345 0.00172 S32 5 0.554483 -0.263339 0.586631 11.00000 0.01168 0.01668 = 0.02805 0.00253 0.00213 0.00067 H22A 2 -0.167948 1.102151 0.370997 11.00000 0.01698 H25B 2 0.902009 0.162123 0.733275 11.00000 0.01889 H22B 2 -0.266295 1.177199 0.389661 11.00000 0.01870 H25A 2 0.805913 0.243522 0.701589 11.00000 0.03941 H26B 2 0.786703 -0.149968 0.702480 11.00000 0.04455 H15A 2 -0.353660 1.131950 0.472501 11.00000 0.04336 H26A 2 0.904958 -0.077736 0.716746 11.00000 0.05058 H15B 2 -0.322647 0.993920 0.506312 11.00000 0.04343 H23 2 0.627071 -0.042472 0.657712 11.00000 0.06161 HKLF 4 REM shelxt_a.res in P2(1)/c REM wR2 = 0.1259, GooF = S = 1.070, Restrained GooF = 1.070 for all data REM R1 = 0.0545 for 4457 Fo > 4sig(Fo) and 0.0575 for all 4675 data REM 363 parameters refined using 0 restraints END WGHT 0.0324 4.9923 REM Highest difference peak 0.636, deepest hole -0.518, 1-sigma level 0.074 Q1 1 0.0904 0.5093 0.6418 11.00000 0.05 0.64 Q2 1 0.6269 0.0971 0.6188 11.00000 0.05 0.60 Q3 1 0.6577 -0.2270 0.6290 11.00000 0.05 0.56 Q4 1 0.0469 0.6421 0.5450 11.00000 0.05 0.50 Q5 1 -0.0780 0.8413 0.4731 11.00000 0.05 0.49 Q6 1 0.3447 0.3349 0.5791 11.00000 0.05 0.48 Q7 1 0.3475 0.4595 0.6762 11.00000 0.05 0.45 Q8 1 0.4998 0.2981 0.6692 11.00000 0.05 0.44 Q9 1 0.6835 0.1508 0.6795 11.00000 0.05 0.44 Q10 1 -0.1360 0.9394 0.4174 11.00000 0.05 0.43 Q11 1 0.9090 0.5160 0.7983 11.00000 0.05 0.43 Q12 1 0.6242 0.2229 0.7017 11.00000 0.05 0.43 Q13 1 0.4615 -0.2622 0.6223 11.00000 0.05 0.42 Q14 1 0.3193 0.4132 0.6098 11.00000 0.05 0.42 Q15 1 0.4849 -0.2734 0.5330 11.00000 0.05 0.38 Q16 1 0.7844 0.5178 0.6835 11.00000 0.05 0.35 Q17 1 0.4215 0.4178 0.7057 11.00000 0.05 0.33 Q18 1 0.0795 0.6574 0.4896 11.00000 0.05 0.32 Q19 1 0.5658 -0.1361 0.5845 11.00000 0.05 0.32 Q20 1 0.5316 0.1399 0.5774 11.00000 0.05 0.31 ; _cod_data_source_file tx2042sup1.cif _cod_data_source_block I _cod_depositor_comments 'Adding full bibliography for 2243912.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2243912 _cod_database_fobs_code 2243912 _shelx_estimated_absorpt_t_min 0.424 _shelx_estimated_absorpt_t_max 0.782 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.1422(2) 0.5583(3) 0.56523(13) 0.0225(5) Uani d 1 . . C C2 0.0580(2) 0.5892(3) 0.60620(13) 0.0237(5) Uani d 1 . . H H2 0.061778 0.544066 0.644799 0.028 Uiso calc 1 . . C C3 -0.0304(2) 0.6865(3) 0.58945(12) 0.0234(5) Uani d 1 . . H H3 -0.086637 0.710328 0.617287 0.028 Uiso calc 1 . . C C4 -0.0384(2) 0.7505(3) 0.53201(12) 0.0225(5) Uani d 1 . . C C5 -0.1241(2) 0.8550(3) 0.51578(12) 0.0229(5) Uani d 1 . . H H5 -0.177017 0.883065 0.544597 0.027 Uiso calc 1 . . C C6 -0.1333(2) 0.9184(3) 0.45831(13) 0.0229(5) Uani d 1 . . C C7 -0.0545(2) 0.8762(3) 0.41562(12) 0.0237(5) Uani d 1 . . H H7 -0.060246 0.917718 0.376162 0.028 Uiso calc 1 . . C C8 0.0302(2) 0.7756(3) 0.43105(12) 0.0228(5) Uani d 1 . . H H8 0.081746 0.747936 0.401556 0.027 Uiso calc 1 . . C C9 0.0437(2) 0.7116(3) 0.48926(12) 0.0221(5) Uani d 1 . . C C10 0.1352(2) 0.6151(3) 0.50758(12) 0.0224(5) Uani d 1 . . H H10 0.191808 0.589251 0.480271 0.027 Uiso calc 1 . . C C12 0.3080(2) 0.4764(3) 0.63457(12) 0.0205(5) Uani d 1 . . C C14 -0.2214(2) 1.0326(3) 0.44424(12) 0.0203(5) Uani d 1 . . C C16 0.4005(2) 0.3658(3) 0.64313(12) 0.0206(5) Uani d 1 . . C C17 0.4753(2) 0.3600(3) 0.69882(12) 0.0223(5) Uani d 1 . . H H17 0.466534 0.426978 0.729554 0.027 Uiso calc 1 . . C C18 0.5632(2) 0.2563(3) 0.70998(12) 0.0222(5) Uani d 1 . . H H18 0.61345 0.252049 0.748167 0.027 Uiso calc 1 . . C C19 0.5758(2) 0.1599(3) 0.66434(12) 0.0217(5) Uani d 1 . . C C20 0.5019(2) 0.1658(3) 0.60820(12) 0.0237(5) Uani d 1 . . H H20 0.51147 0.100093 0.577062 0.028 Uiso calc 1 . . C C21 0.4145(2) 0.2678(3) 0.59814(12) 0.0229(5) Uani d 1 . . H H21 0.363537 0.271047 0.560152 0.027 Uiso calc 1 . . C C24 0.7756(2) 0.0499(3) 0.69864(12) 0.0212(5) Uani d 1 . . C C30 0.7107(2) 0.5832(3) 0.76962(13) 0.0245(6) Uani d 1 . . H H30A 0.661242 0.637008 0.738122 0.037 Uiso calc 1 . . H H30B 0.734263 0.641357 0.805571 0.037 Uiso calc 1 . . H H30C 0.663287 0.504665 0.781635 0.037 Uiso calc 1 . . C C35 0.6293(2) -0.4167(3) 0.57039(13) 0.0262(6) Uani d 1 . . H H35A 0.717501 -0.403331 0.578279 0.039 Uiso calc 1 . . H H35B 0.607172 -0.441466 0.527188 0.039 Uiso calc 1 . . H H35C 0.604676 -0.490755 0.596665 0.039 Uiso calc 1 . . N N15 -0.3033(2) 1.0565(3) 0.48204(11) 0.0238(5) Uani d 1 . . N N22 -0.2175(2) 1.1128(2) 0.39642(11) 0.0214(5) Uani d 1 . . N N23 0.65733(19) 0.0475(2) 0.67377(11) 0.0242(5) Uani d 1 . . N N25 0.8365(2) 0.1631(2) 0.71094(12) 0.0242(5) Uani d 1 . . N N26 0.8283(2) -0.0718(2) 0.70825(12) 0.0252(5) Uani d 1 . . O O11 0.23387(15) 0.46189(19) 0.57993(8) 0.0217(4) Uani d 1 . . O O13 0.29656(16) 0.5684(2) 0.67019(9) 0.0255(4) Uani d 1 . . O O28 0.80155(16) 0.44602(19) 0.68474(8) 0.0234(4) Uani d 1 . . O O29 0.91327(16) 0.64512(19) 0.72854(9) 0.0252(4) Uani d 1 . . O O31 0.90733(15) 0.43603(19) 0.78786(8) 0.0221(4) Uani d 1 . . O O33 0.42506(16) -0.2921(2) 0.57331(10) 0.0308(5) Uani d 1 . . O O34 0.59193(17) -0.1572(2) 0.54595(9) 0.0282(4) Uani d 1 . . O O36 0.59191(19) -0.2314(2) 0.65057(9) 0.0308(4) Uani d 1 . . S S27 0.84252(5) 0.52334(6) 0.73995(3) 0.01897(15) Uani d 1 . . S S32 0.55448(5) -0.26334(6) 0.58663(3) 0.01882(15) Uani d 1 . . H H22A -0.168(3) 1.102(3) 0.3710(14) 0.017(7) Uiso d 1 . . H H25B 0.902(3) 0.162(3) 0.7333(14) 0.019(7) Uiso d 1 . . H H22B -0.266(3) 1.177(3) 0.3897(13) 0.019(7) Uiso d 1 . . H H25A 0.806(3) 0.244(4) 0.7016(17) 0.039(10) Uiso d 1 . . H H26B 0.787(3) -0.150(4) 0.7025(17) 0.045(10) Uiso d 1 . . H H15A -0.354(3) 1.132(4) 0.4725(17) 0.043(10) Uiso d 1 . . H H26A 0.905(4) -0.078(4) 0.7167(18) 0.051(11) Uiso d 1 . . H H15B -0.323(3) 0.994(4) 0.5063(18) 0.043(10) Uiso d 1 . . H H23 0.627(4) -0.042(5) 0.6577(19) 0.062(12) Uiso d 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0136(11) 0.0182(13) 0.0341(14) 0.0017(9) -0.0030(10) -0.0012(10) C2 0.0163(12) 0.0241(14) 0.0307(14) -0.0010(10) 0.0023(10) 0.0018(11) C3 0.0134(11) 0.0253(14) 0.0324(14) 0.0000(10) 0.0060(10) -0.0028(11) C4 0.0129(11) 0.0224(13) 0.0319(14) -0.0016(10) 0.0021(10) -0.0035(11) C5 0.0141(11) 0.0245(14) 0.0306(13) -0.0018(10) 0.0047(10) -0.0030(11) C6 0.0126(11) 0.0194(13) 0.0359(14) -0.0009(9) 0.0002(10) -0.0011(11) C7 0.0184(12) 0.0250(14) 0.0271(13) -0.0014(10) 0.0005(10) 0.0011(10) C8 0.0160(12) 0.0217(13) 0.0301(13) 0.0023(10) 0.0008(10) -0.0031(10) C9 0.0156(11) 0.0249(14) 0.0256(13) -0.0039(10) 0.0015(10) -0.0012(10) C10 0.0177(12) 0.0224(14) 0.0277(13) -0.0004(10) 0.0051(10) -0.0012(10) C12 0.0138(11) 0.0196(13) 0.0286(13) -0.0014(9) 0.0050(10) -0.0004(10) C14 0.0114(11) 0.0187(13) 0.0303(13) -0.0028(9) 0.0000(9) -0.0012(10) C16 0.0126(11) 0.0201(13) 0.0293(13) -0.0013(9) 0.0033(9) 0.0019(10) C17 0.0170(12) 0.0255(14) 0.0244(12) -0.0037(10) 0.0018(10) 0.0002(10) C18 0.0182(12) 0.0219(13) 0.0259(13) -0.0015(10) 0.0000(10) -0.0001(10) C19 0.0144(11) 0.0218(13) 0.0290(13) -0.0016(10) 0.0029(10) 0.0020(10) C20 0.0166(12) 0.0250(14) 0.0290(13) 0.0003(10) 0.0010(10) 0.0008(11) C21 0.0209(12) 0.0217(13) 0.0270(13) -0.0021(10) 0.0069(10) 0.0000(10) C24 0.0142(11) 0.0256(14) 0.0247(12) 0.0026(10) 0.0057(9) 0.0020(10) C30 0.0151(12) 0.0286(15) 0.0301(14) 0.0051(10) 0.0035(10) 0.0020(11) C35 0.0194(12) 0.0225(14) 0.0359(15) 0.0023(10) 0.0004(11) 0.0014(11) N15 0.0169(10) 0.0226(12) 0.0324(12) 0.0037(9) 0.0054(9) 0.0062(10) N22 0.0149(10) 0.0217(12) 0.0280(12) 0.0019(9) 0.0037(9) 0.0004(9) N23 0.0137(10) 0.0245(12) 0.0334(12) 0.0027(9) -0.0012(9) -0.0001(10) N25 0.0160(11) 0.0187(12) 0.0378(13) 0.0028(9) 0.0037(10) 0.0035(10) N26 0.0146(11) 0.0202(12) 0.0409(14) 0.0014(9) 0.0034(9) 0.0005(10) O11 0.0142(8) 0.0238(10) 0.0267(9) 0.0021(7) 0.0002(7) -0.0028(7) O13 0.0184(9) 0.0270(10) 0.0310(10) 0.0029(7) 0.0019(7) -0.0023(8) O28 0.0234(9) 0.0202(9) 0.0264(9) 0.0013(7) 0.0021(7) -0.0010(7) O29 0.0202(9) 0.0200(10) 0.0358(10) -0.0005(7) 0.0059(8) 0.0036(8) O31 0.0136(8) 0.0236(10) 0.0288(9) 0.0045(7) 0.0012(7) 0.0060(7) O33 0.0126(9) 0.0248(10) 0.0547(13) 0.0006(7) 0.0027(8) 0.0066(9) O34 0.0288(10) 0.0214(10) 0.0358(11) 0.0005(8) 0.0102(8) 0.0067(8) O36 0.0398(11) 0.0225(10) 0.0282(10) 0.0011(8) -0.0038(8) 0.0013(8) S27 0.0124(3) 0.0184(3) 0.0264(3) 0.0017(2) 0.0034(2) 0.0019(2) S32 0.0117(3) 0.0167(3) 0.0281(3) 0.0007(2) 0.0021(2) 0.0025(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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C10 C1 O11 . . 116.5(2) ? C10 C1 C2 . . 122.3(2) ? O11 C1 C2 . . 121.2(2) ? C3 C2 C1 . . 118.7(2) ? C3 C2 H2 . . 120.6 ? C1 C2 H2 . . 120.6 ? C2 C3 C4 . . 120.8(2) ? C2 C3 H3 . . 119.6 ? C4 C3 H3 . . 119.6 ? C3 C4 C5 . . 121.2(2) ? C3 C4 C9 . . 119.7(2) ? C5 C4 C9 . . 119.1(2) ? C6 C5 C4 . . 121.5(2) ? C6 C5 H5 . . 119.3 ? C4 C5 H5 . . 119.3 ? C5 C6 C7 . . 119.0(2) ? C5 C6 C14 . . 119.6(2) ? C7 C6 C14 . . 121.3(2) ? C8 C7 C6 . . 120.1(2) ? C8 C7 H7 . . 120 ? C6 C7 H7 . . 120 ? C7 C8 C9 . . 122.3(2) ? C7 C8 H8 . . 118.8 ? C9 C8 H8 . . 118.8 ? C10 C9 C8 . . 123.3(2) ? C10 C9 C4 . . 118.7(2) ? C8 C9 C4 . . 117.9(2) ? C1 C10 C9 . . 119.6(2) ? C1 C10 H10 . . 120.2 ? C9 C10 H10 . . 120.2 ? O13 C12 O11 . . 122.9(2) ? O13 C12 C16 . . 125.5(2) ? O11 C12 C16 . . 111.6(2) ? N22 C14 N15 . . 119.1(2) ? N22 C14 C6 . . 121.9(2) ? N15 C14 C6 . . 119.0(2) ? C17 C16 C21 . . 119.3(2) ? C17 C16 C12 . . 118.1(2) ? C21 C16 C12 . . 122.6(2) ? C16 C17 C18 . . 120.7(2) ? C16 C17 H17 . . 119.7 ? C18 C17 H17 . . 119.7 ? C19 C18 C17 . . 119.0(2) ? C19 C18 H18 . . 120.5 ? C17 C18 H18 . . 120.5 ? C18 C19 C20 . . 120.6(2) ? C18 C19 N23 . . 122.1(2) ? C20 C19 N23 . . 117.2(2) ? C21 C20 C19 . . 119.7(3) ? C21 C20 H20 . . 120.2 ? C19 C20 H20 . . 120.2 ? C20 C21 C16 . . 120.7(3) ? C20 C21 H21 . . 119.6 ? C16 C21 H21 . . 119.6 ? N25 C24 N26 . . 121.0(2) ? N25 C24 N23 . . 123.3(2) ? N26 C24 N23 . . 115.7(2) ? S27 C30 H30A . . 109.5 ? S27 C30 H30B . . 109.5 ? H30A C30 H30B . . 109.5 ? S27 C30 H30C . . 109.5 ? H30A C30 H30C . . 109.5 ? H30B C30 H30C . . 109.5 ? S32 C35 H35A . . 109.5 ? S32 C35 H35B . . 109.5 ? H35A C35 H35B . . 109.5 ? S32 C35 H35C . . 109.5 ? H35A C35 H35C . . 109.5 ? H35B C35 H35C . . 109.5 ? C14 N15 H15A . . 116(2) ? C14 N15 H15B . . 120(3) ? H15A N15 H15B . . 121(3) ? C14 N22 H22A . . 123(2) ? C14 N22 H22B . . 121(2) ? H22A N22 H22B . . 116(3) ? C24 N23 C19 . . 127.7(2) ? C24 N23 H23 . . 115(2) ? C19 N23 H23 . . 117(2) ? C24 N25 H25B . . 121(2) ? C24 N25 H25A . . 122(2) ? H25B N25 H25A . . 116(3) ? C24 N26 H26B . . 122(2) ? C24 N26 H26A . . 120(3) ? H26B N26 H26A . . 117(4) ? C12 O11 C1 . . 118.4(2) ? O28 S27 O29 . . 113.51(11) ? O28 S27 O31 . . 112.04(11) ? O29 S27 O31 . . 111.41(11) ? O28 S27 C30 . . 106.72(12) ? O29 S27 C30 . . 106.21(12) ? O31 S27 C30 . . 106.39(12) ? O36 S32 O33 . . 113.48(13) ? O36 S32 O34 . . 111.82(12) ? O33 S32 O34 . . 110.96(12) ? O36 S32 C35 . . 106.84(13) ? O33 S32 C35 . . 105.73(12) ? O34 S32 C35 . . 107.57(12) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 O11 . 1.391(3) y C1 C2 . 1.401(4) ? C1 C10 . 1.373(4) ? C10 H10 . 0.95 ? C12 O13 . 1.204(3) y C12 O11 . 1.377(3) y C12 C16 . 1.481(3) ? C14 N22 . 1.311(3) y C14 N15 . 1.319(3) y C16 C21 . 1.393(4) ? C16 C17 . 1.393(4) ? C17 H17 . 0.95 ? C17 C18 . 1.402(4) ? C18 H18 . 0.95 ? C18 C19 . 1.390(4) ? C19 N23 . 1.417(3) y C19 C20 . 1.397(4) ? C2 H2 . 0.95 ? C2 C3 . 1.379(4) ? C20 H20 . 0.95 ? C20 C21 . 1.384(4) ? C21 H21 . 0.95 ? C24 N26 . 1.325(3) y C24 N25 . 1.302(4) y C24 N23 . 1.357(3) y C3 H3 . 0.95 ? C3 C4 . 1.398(4) ? C30 S27 . 1.764(3) y C30 H30C . 0.98 ? C30 H30B . 0.98 ? C30 H30A . 0.98 ? C35 S32 . 1.762(3) y C35 H35C . 0.98 ? C35 H35B . 0.98 ? C35 H35A . 0.98 ? C4 C9 . 1.430(4) ? C4 C5 . 1.407(4) ? C5 H5 . 0.95 ? C5 C6 . 1.396(4) ? C6 C7 . 1.413(4) ? C6 C14 . 1.486(3) ? C7 H7 . 0.95 ? C7 C8 . 1.369(4) ? C8 H8 . 0.95 ? C8 C9 . 1.412(4) ? C9 C10 . 1.403(4) ? N15 H15B . 0.85(4) ? N15 H15A . 0.93(4) ? N22 H22B . 0.83(3) ? N22 H22A . 0.83(3) ? N23 H23 . 0.99(4) ? N25 H25B . 0.83(3) ? N25 H25A . 0.87(4) ? N26 H26B . 0.89(4) ? N26 H26A . 0.85(4) ? O28 S27 . 1.4515(19) y O29 S27 . 1.4570(19) y O31 S27 . 1.4700(18) y O33 S32 . 1.4545(18) y O34 S32 . 1.4553(19) y O36 S32 . 1.448(2) y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C18 H18 O13 2_646 0.95 2.64 3.419(3) 139.7 yes C30 H30A O36 1_565 0.98 2.36 3.314(3) 164.6 yes N15 H15A O33 3_566 0.93(4) 1.97(4) 2.854(3) 159(3) yes N15 H15A O34 3_566 0.93(4) 2.63(4) 3.327(3) 132(3) yes N15 H15A S32 3_566 0.93(4) 2.75(4) 3.612(2) 154(3) yes N15 H15B O34 1_465 0.85(4) 2.00(4) 2.830(3) 164(4) yes N22 H22A O31 4_475 0.83(3) 2.12(3) 2.928(3) 162(3) yes N22 H22B O33 3_566 0.83(3) 2.31(3) 3.018(3) 144(3) yes N23 H23 O36 . 0.99(4) 1.88(5) 2.836(3) 163(4) yes N23 H23 S32 . 0.99(4) 2.72(4) 3.683(2) 166(3) yes N25 H25A O28 . 0.87(4) 2.00(4) 2.827(3) 159(3) yes N25 H25A S27 . 0.87(4) 2.86(4) 3.558(2) 139(3) yes N25 H25B O29 2_746 0.83(3) 2.12(3) 2.931(3) 167(3) yes N26 H26A O31 2_746 0.85(4) 2.10(4) 2.916(3) 163(4) yes N26 H26A S27 2_746 0.85(4) 3.01(4) 3.799(2) 156(3) yes N26 H26B O29 1_545 0.89(4) 2.46(4) 2.925(3) 113(3) yes N26 H26B O36 . 0.89(4) 2.45(4) 3.174(3) 139(3) yes C30 H30B Cg(C) 1_545 0.98 2.96 3.405(3) 109 yes