#------------------------------------------------------------------------------ #$Date: 2019-02-22 03:59:13 +0200 (Fri, 22 Feb 2019) $ #$Revision: 213783 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/82/7058204.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_7058204 loop_ _publ_author_name 'Zou, Dongyu' 'Liu, Lixin' 'Zhang, Dajun' 'Zhang, Yunan' 'Zhang, Yu' 'Zhang, Qiang' 'Wang, Jian' 'Zeng, Shaoyu' 'Wang, Conggang' _publ_section_title ; Assembly of three Pharmaceutical salts/cocrystals of tetrahydroberberine with sulfophenyl acids: improving the properties by formation of charge-assisted hydrogen bonds ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ00131J _journal_year 2019 _chemical_formula_moiety 'C7 H7 O3 S, C20 H22 N O4, 1(C H4 O)' _chemical_formula_sum 'C28 H33 N O8 S' _chemical_formula_weight 543.61 _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 mixed _audit_creation_date 2018-11-07 _audit_creation_method ; Olex2 1.2-beta (compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203) ; _audit_update_record ; 2018-12-05 deposited with the CCDC. 2019-02-19 downloaded from the CCDC. ; _cell_angle_alpha 68.593(7) _cell_angle_beta 83.020(6) _cell_angle_gamma 74.648(7) _cell_formula_units_Z 2 _cell_length_a 8.2161(5) _cell_length_b 11.8768(11) _cell_length_c 15.3082(11) _cell_measurement_reflns_used 6458 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.65 _cell_measurement_theta_min 2.06 _cell_volume 1340.59(19) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 298.15 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.833 _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 0.0291 _diffrn_reflns_av_unetI/netI 0.0558 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.833 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 11366 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.833 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.264 _diffrn_reflns_theta_min 3.468 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48219 _exptl_absorpt_correction_type multi-scan _exptl_crystal_density_diffrn 1.347 _exptl_crystal_description block _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.488 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 364 _refine_ls_number_reflns 6102 _refine_ls_number_restraints 99 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0601 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0839P)^2^+0.2444P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1527 _refine_ls_wR_factor_ref 0.1818 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4024 _reflns_number_total 6102 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL SIR97 run in space group P -1 zdy3.res created by SHELXL-2016/6 at 13:34:11 on 07-Nov-2018 CELL 0.71073 8.2161 11.8768 15.3082 68.593 83.02 74.648 ZERR 2 0.0005 0.0011 0.0011 0.007 0.006 0.007 LATT 1 SFAC C H N O S UNIT 56 66 2 16 2 DFIX 1.5 0.005 O10 C29 C30 O9 DFIX 1.5 0.005 O8 C28 SIMU 0.01 0.02 2 C30 > O8 ISOR 0.01 0.02 O9 ISOR 0.01 0.02 C30 C29 O10 O9 ISOR 0.01 0.02 O8 C28 C30 O9 O10 C29 L.S. 18 PLAN 2 SIZE 0.25 0.27 0.43 TEMP 25 BOND $H CONF MORE -1 fmap 2 acta MERG 2 OMIT -1 0 1 OMIT 0 0 2 OMIT 1 1 2 OMIT 1 0 1 OMIT 1 -3 1 OMIT 0 1 3 OMIT 1 4 5 OMIT 1 1 6 OMIT 1 0 6 OMIT 3 -3 3 OMIT 2 0 7 OMIT -2 2 7 OMIT 2 2 4 OMIT -3 -2 4 OMIT 2 4 0 OMIT -2 2 5 OMIT 2 -2 5 OMIT 0 6 2 OMIT -2 -1 2 OMIT 1 1 4 REM REM REM WGHT 0.083900 0.244400 FVAR 0.17506 S1 5 0.861261 0.341543 0.129710 11.00000 0.03170 0.03741 = 0.04128 -0.00693 -0.00025 -0.00679 N1 3 0.470309 0.262898 0.136758 11.00000 0.02835 0.03106 = 0.03550 -0.00853 -0.00003 -0.00507 AFIX 13 H1 2 0.583788 0.249189 0.158360 11.00000 -1.20000 AFIX 0 O1 4 1.026831 0.292803 0.096139 11.00000 0.03795 0.05575 = 0.06184 -0.02665 0.00972 -0.01051 O2 4 0.747765 0.425083 0.056400 11.00000 0.05370 0.05117 = 0.05417 -0.00016 -0.01681 -0.00800 O3 4 0.830755 0.110800 -0.183910 11.00000 0.06759 0.05372 = 0.04911 -0.01826 0.02103 0.00043 O4 4 0.207323 0.079692 0.565236 11.00000 0.11652 0.06646 = 0.04063 -0.01825 0.02228 -0.02148 C1 1 0.590087 0.171386 0.015446 11.00000 0.02775 0.03403 = 0.03856 -0.01118 -0.00111 -0.00645 C2 1 0.354976 0.138987 0.289143 11.00000 0.03221 0.03780 = 0.03599 -0.00851 0.00085 -0.00760 C3 1 0.616750 0.054213 0.084569 11.00000 0.03035 0.03330 = 0.03840 -0.01362 -0.00109 -0.00598 O5 4 0.785879 0.243021 0.196437 11.00000 0.04043 0.04083 = 0.04625 -0.00711 -0.00021 -0.01448 C4 1 0.318427 0.026751 0.350523 11.00000 0.05799 0.04339 = 0.04191 -0.01406 0.00645 -0.01659 AFIX 43 H4 2 0.326405 -0.039234 0.329989 11.00000 -1.20000 AFIX 0 O6 4 0.640318 0.304615 -0.139888 11.00000 0.05784 0.03854 = 0.04147 -0.00541 0.00704 -0.01324 O7 4 0.227042 -0.081583 0.511644 11.00000 0.11931 0.05705 = 0.04387 -0.01159 0.02736 -0.03363 C5 1 0.406922 0.148977 0.189291 11.00000 0.03138 0.03235 = 0.03760 -0.01019 0.00154 -0.00895 AFIX 13 H5 2 0.307190 0.153994 0.157576 11.00000 -1.20000 AFIX 0 C6 1 0.717530 -0.045945 0.062536 11.00000 0.04799 0.03167 = 0.04308 -0.00916 -0.00216 -0.00639 AFIX 43 H6 2 0.735692 -0.124965 0.108278 11.00000 -1.20000 AFIX 0 C7 1 0.483430 0.284471 0.033981 11.00000 0.03708 0.03320 = 0.03519 -0.00717 0.00184 -0.00365 AFIX 23 H7A 2 0.532921 0.354937 0.001358 11.00000 -1.20000 H7B 2 0.371454 0.304052 0.010069 11.00000 -1.20000 AFIX 0 C1AA 1 0.765093 0.085381 -0.094294 11.00000 0.03867 0.04664 = 0.04324 -0.01899 0.00786 -0.00997 C2AA 1 0.891478 0.431604 0.193634 11.00000 0.02982 0.03516 = 0.04853 -0.00998 0.00227 -0.00369 C0AA 1 0.543713 0.036900 0.181832 11.00000 0.04689 0.03108 = 0.03944 -0.00784 0.00053 -0.00730 AFIX 23 H0AA 2 0.633964 0.020350 0.223465 11.00000 -1.20000 H0AB 2 0.496167 -0.035517 0.203130 11.00000 -1.20000 AFIX 0 C11 1 0.662930 0.187337 -0.073665 11.00000 0.03639 0.03440 = 0.04197 -0.01126 0.00284 -0.00803 C12 1 0.338364 0.236912 0.321141 11.00000 0.03836 0.04018 = 0.04174 -0.01531 0.00191 -0.00407 C13 1 0.361837 0.374586 0.154825 11.00000 0.03795 0.02909 = 0.04830 -0.01286 0.00727 -0.00150 AFIX 23 H13A 2 0.245775 0.385214 0.140422 11.00000 -1.20000 H13B 2 0.399255 0.448325 0.114941 11.00000 -1.20000 AFIX 0 C14 1 0.791801 -0.031586 -0.025595 11.00000 0.04192 0.03919 = 0.05071 -0.02186 0.00044 0.00000 AFIX 43 H14 2 0.859392 -0.100212 -0.038648 11.00000 -1.20000 AFIX 0 C15 1 0.270954 0.017332 0.441002 11.00000 0.05846 0.04623 = 0.03893 -0.00682 0.00626 -0.01431 C16 1 0.289141 0.223888 0.414360 11.00000 0.06759 0.04853 = 0.04488 -0.02069 0.00466 -0.01066 AFIX 43 H16 2 0.277921 0.289302 0.436029 11.00000 -1.20000 AFIX 0 C17 1 0.372624 0.358299 0.255915 11.00000 0.04938 0.03895 = 0.04895 -0.01894 0.00763 -0.00920 AFIX 23 H17A 2 0.291580 0.426201 0.269459 11.00000 -1.20000 H17B 2 0.484456 0.362203 0.266949 11.00000 -1.20000 AFIX 0 C18 1 0.941075 0.541486 0.145373 11.00000 0.03942 0.03786 = 0.06061 -0.01193 0.00670 -0.00552 AFIX 43 H18 2 0.955708 0.567827 0.080416 11.00000 -1.20000 AFIX 0 C19 1 0.871186 0.392799 0.289516 11.00000 0.06384 0.04544 = 0.05112 -0.01270 0.00341 -0.01966 AFIX 43 H19 2 0.839368 0.318557 0.322310 11.00000 -1.20000 AFIX 0 C20 1 0.964570 0.016777 -0.201341 11.00000 0.04802 0.06248 = 0.06132 -0.03482 0.01672 -0.01152 AFIX 137 H20A 2 1.011009 0.049069 -0.263528 11.00000 -1.50000 H20B 2 0.922034 -0.053484 -0.195845 11.00000 -1.50000 H20C 2 1.050984 -0.008713 -0.156414 11.00000 -1.50000 AFIX 0 C21 1 0.258194 0.113977 0.472344 11.00000 0.06113 0.05438 = 0.03720 -0.01555 0.00568 -0.00959 C22 1 0.968684 0.611769 0.194577 11.00000 0.04646 0.03912 = 0.09553 -0.02098 0.00803 -0.01167 AFIX 43 H22 2 1.002486 0.685256 0.161922 11.00000 -1.20000 AFIX 0 C23 1 0.947435 0.575721 0.290146 11.00000 0.06521 0.06311 = 0.08965 -0.03772 0.00874 -0.02337 C24 1 0.898799 0.465932 0.337465 11.00000 0.08827 0.06924 = 0.06079 -0.02698 0.00677 -0.02845 AFIX 43 H24 2 0.884102 0.440065 0.402411 11.00000 -1.20000 AFIX 0 C25 1 0.200517 -0.047043 0.592461 11.00000 0.09457 0.06784 = 0.04100 -0.01169 0.01550 -0.01970 AFIX 23 H25A 2 0.286846 -0.099586 0.637655 11.00000 -1.20000 H25B 2 0.091271 -0.057533 0.621535 11.00000 -1.20000 AFIX 0 C26 1 0.519706 0.332698 -0.207374 11.00000 0.09208 0.06194 = 0.07274 -0.00115 -0.02819 -0.01496 AFIX 137 H26A 2 0.519306 0.412934 -0.254145 11.00000 -1.50000 H26B 2 0.409941 0.333663 -0.177417 11.00000 -1.50000 H26C 2 0.547641 0.270642 -0.236570 11.00000 -1.50000 AFIX 0 C27 1 0.978142 0.653365 0.343284 11.00000 0.15289 0.10697 = 0.13176 -0.07428 0.01447 -0.06392 AFIX 137 H27A 2 1.091726 0.663546 0.330774 11.00000 -1.50000 H27B 2 0.961740 0.612154 0.409374 11.00000 -1.50000 H27C 2 0.900414 0.733582 0.323367 11.00000 -1.50000 AFIX 0 PART -2 C30 1 10.574800 10.463981 10.531469 10.33333 0.11093 0.09007 = 0.11065 -0.04390 -0.02820 -0.04914 AFIX 3 H30A 2 0.501770 0.521310 0.481620 10.33333 -1.50000 H30B 2 0.682250 0.484960 0.522070 10.33333 -1.50000 H30C 2 0.525020 0.468780 0.590470 10.33333 -1.50000 AFIX 0 O9 4 10.600440 10.338861 10.533400 10.33333 0.12921 0.09889 = 0.17472 -0.05638 0.03832 -0.04124 AFIX 3 H9 2 0.709440 0.289990 0.557230 10.33333 -1.50000 AFIX 0 PART 0 PART -1 O10 4 10.626161 10.518391 10.548170 10.33333 0.15287 0.07937 = 0.11611 -0.04137 -0.02103 -0.01205 AFIX 3 H10 2 0.685020 0.432150 0.569790 10.33333 -1.50000 AFIX 0 C29 1 10.483469 10.533680 10.498700 10.33333 0.12772 0.10303 = 0.15620 -0.04180 0.03878 -0.04736 AFIX 3 H29A 2 0.517130 0.499200 0.449660 10.33333 -1.50000 H29B 2 0.431750 0.620900 0.471730 10.33333 -1.50000 H29C 2 0.404130 0.492010 0.540850 10.33333 -1.50000 AFIX 0 PART 0 PART -3 C28 1 10.455850 10.447160 10.494529 10.33333 0.16145 0.11517 = 0.17149 -0.06449 0.00391 -0.03148 AFIX 3 H28A 2 0.462890 0.454220 0.429750 10.33333 -1.50000 H28B 2 0.520450 0.498740 0.503070 10.33333 -1.50000 H28C 2 0.340030 0.473640 0.512540 10.33333 -1.50000 AFIX 0 O8 4 10.512589 10.321051 10.557080 10.33333 0.18716 0.12206 = 0.17465 -0.06770 -0.04135 -0.01902 AFIX 3 H8 2 0.601230 0.316110 0.594780 10.33333 -1.50000 AFIX 0 HKLF 4 REM SIR97 run in space group P -1 REM R1 = 0.0601 for 4024 Fo > 4sig(Fo) and 0.0957 for all 6102 data REM 364 parameters refined using 99 restraints END WGHT 0.0791 0.2676 REM Highest difference peak 0.488, deepest hole -0.450, 1-sigma level 0.054 Q1 1 0.4316 0.2787 0.5911 11.00000 0.05 0.49 Q2 1 0.5546 0.3562 0.4836 11.00000 0.05 0.43 REM The information below was added by Olex2. REM REM R1 = 0.0601 for 4024 Fo > 4sig(Fo) and 0.0957 for all 11419 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.49, deepest hole -0.45 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0957 REM R1_gt = 0.0601 REM wR_ref = n/a REM GOOF = n/a REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 11419 REM Reflections_gt = 4024 REM Parameters = n/a REM Hole = -0.45 REM Peak = 0.49 REM Flack = n/a ; _cod_data_source_file c9nj00131j2.cif _cod_data_source_block zdy3 _cod_database_code 7058204 _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 0.958 _shelx_estimated_absorpt_t_min 0.930 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Restrained distances O10-C29 = C30-O9 1.5 with sigma of 0.005 O8-C28 1.5 with sigma of 0.005 3. Uiso/Uaniso restraints and constraints C30 \\sim O9 \\sim O10 \\sim C29 \\sim C28 \\sim O8: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C30) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(O9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(O8) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 4. Others Fixed Sof: C30(0.33333) H30A(0.33333) H30B(0.33333) H30C(0.33333) O9(0.33333) H9(0.33333) O10(0.33333) H10(0.33333) C29(0.33333) H29A(0.33333) H29B(0.33333) H29C(0.33333) C28(0.33333) H28A(0.33333) H28B(0.33333) H28C(0.33333) O8(0.33333) H8(0.33333) Fixed X: C30(0.5748) O9(0.60044) O10(0.626161) C29(0.483469) C28(0.45585) O8(0.512589) Fixed Y: C30(0.463981) O9(0.338861) O10(0.518391) C29(0.53368) C28(0.44716) O8(0.321051) Fixed Z: C30(0.531469) O9(0.5334) O10(0.54817) C29(0.4987) C28(0.494529) O8(0.55708) 5.a Riding coordinates: C30(H30A,H30B,H30C), O9(H9), O10(H10), C29(H29A,H29B,H29C), C28(H28A,H28B, H28C), O8(H8) 5.b Ternary CH refined with riding coordinates: N1(H1), C5(H5) 5.c Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C0AA(H0AA,H0AB), C13(H13A,H13B), C17(H17A,H17B), C25(H25A,H25B) 5.d Aromatic/amide H refined with riding coordinates: C4(H4), C6(H6), C14(H14), C16(H16), C18(H18), C19(H19), C22(H22), C24(H24) 5.e Idealised Me refined as rotating group: C20(H20A,H20B,H20C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C) ; _shelx_shelxl_version_number 2016/6 _olex2_submission_special_instructions 'No special instructions were received' 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 0.86126(7) 0.34154(6) 0.12971(5) 0.0391(2) Uani 1 1 d . . . . . N1 N 0.4703(2) 0.26290(17) 0.13676(14) 0.0330(4) Uani 1 1 d . . . . . H1 H 0.583788 0.249189 0.158360 0.040 Uiso 1 1 calc R . . . . O1 O 1.0268(2) 0.29280(18) 0.09614(14) 0.0512(5) Uani 1 1 d . . . . . O2 O 0.7478(2) 0.42508(18) 0.05640(15) 0.0578(6) Uani 1 1 d . . . . . O3 O 0.8308(3) 0.11080(19) -0.18391(15) 0.0618(6) Uani 1 1 d . . . . . O4 O 0.2073(3) 0.0797(2) 0.56524(15) 0.0769(7) Uani 1 1 d . . . . . C1 C 0.5901(3) 0.1714(2) 0.01545(17) 0.0340(5) Uani 1 1 d . . . . . C2 C 0.3550(3) 0.1390(2) 0.28914(18) 0.0369(5) Uani 1 1 d . . . . . C3 C 0.6167(3) 0.0542(2) 0.08457(17) 0.0340(5) Uani 1 1 d . . . . . O5 O 0.7859(2) 0.24302(16) 0.19644(13) 0.0439(4) Uani 1 1 d . . . . . C4 C 0.3184(3) 0.0268(3) 0.3505(2) 0.0478(7) Uani 1 1 d . . . . . H4 H 0.326405 -0.039234 0.329989 0.057 Uiso 1 1 calc R . . . . O6 O 0.6403(2) 0.30462(16) -0.13989(13) 0.0488(5) Uani 1 1 d . . . . . O7 O 0.2270(3) -0.0816(2) 0.51164(16) 0.0753(7) Uani 1 1 d . . . . . C5 C 0.4069(3) 0.1490(2) 0.18929(17) 0.0343(5) Uani 1 1 d . . . . . H5 H 0.307190 0.153994 0.157576 0.041 Uiso 1 1 calc R . . . . C6 C 0.7175(3) -0.0459(2) 0.06254(19) 0.0426(6) Uani 1 1 d . . . . . H6 H 0.735692 -0.124965 0.108278 0.051 Uiso 1 1 calc R . . . . C7 C 0.4834(3) 0.2845(2) 0.03398(17) 0.0377(6) Uani 1 1 d . . . . . H7A H 0.532921 0.354937 0.001358 0.045 Uiso 1 1 calc R . . . . H7B H 0.371454 0.304052 0.010069 0.045 Uiso 1 1 calc R . . . . C1AA C 0.7651(3) 0.0854(3) -0.09429(19) 0.0427(6) Uani 1 1 d . . . . . C2AA C 0.8915(3) 0.4316(2) 0.19363(19) 0.0403(6) Uani 1 1 d . . . . . C0AA C 0.5437(3) 0.0369(2) 0.18183(18) 0.0410(6) Uani 1 1 d . . . . . H0AA H 0.633964 0.020350 0.223465 0.049 Uiso 1 1 calc R . . . . H0AB H 0.496167 -0.035517 0.203130 0.049 Uiso 1 1 calc R . . . . C11 C 0.6629(3) 0.1873(2) -0.07367(18) 0.0386(6) Uani 1 1 d . . . . . C12 C 0.3384(3) 0.2369(2) 0.32114(19) 0.0411(6) Uani 1 1 d . . . . . C13 C 0.3618(3) 0.3746(2) 0.15482(19) 0.0407(6) Uani 1 1 d . . . . . H13A H 0.245775 0.385214 0.140422 0.049 Uiso 1 1 calc R . . . . H13B H 0.399255 0.448325 0.114941 0.049 Uiso 1 1 calc R . . . . C14 C 0.7918(3) -0.0316(2) -0.0256(2) 0.0443(6) Uani 1 1 d . . . . . H14 H 0.859392 -0.100212 -0.038648 0.053 Uiso 1 1 calc R . . . . C15 C 0.2710(4) 0.0173(3) 0.4410(2) 0.0505(7) Uani 1 1 d . . . . . C16 C 0.2891(4) 0.2239(3) 0.4144(2) 0.0536(7) Uani 1 1 d . . . . . H16 H 0.277921 0.289302 0.436029 0.064 Uiso 1 1 calc R . . . . C17 C 0.3726(3) 0.3583(2) 0.2559(2) 0.0458(6) Uani 1 1 d . . . . . H17A H 0.291580 0.426201 0.269459 0.055 Uiso 1 1 calc R . . . . H17B H 0.484456 0.362203 0.266949 0.055 Uiso 1 1 calc R . . . . C18 C 0.9411(3) 0.5415(2) 0.1454(2) 0.0489(7) Uani 1 1 d . . . . . H18 H 0.955708 0.567827 0.080416 0.059 Uiso 1 1 calc R . . . . C19 C 0.8712(4) 0.3928(3) 0.2895(2) 0.0538(7) Uani 1 1 d . . . . . H19 H 0.839368 0.318557 0.322310 0.065 Uiso 1 1 calc R . . . . C20 C 0.9646(4) 0.0168(3) -0.2013(2) 0.0554(8) Uani 1 1 d . . . . . H20A H 1.011009 0.049069 -0.263528 0.083 Uiso 1 1 calc GR . . . . H20B H 0.922034 -0.053484 -0.195845 0.083 Uiso 1 1 calc GR . . . . H20C H 1.050984 -0.008713 -0.156414 0.083 Uiso 1 1 calc GR . . . . C21 C 0.2582(4) 0.1140(3) 0.4723(2) 0.0525(7) Uani 1 1 d . . . . . C22 C 0.9687(4) 0.6118(3) 0.1946(3) 0.0617(9) Uani 1 1 d . . . . . H22 H 1.002486 0.685256 0.161922 0.074 Uiso 1 1 calc R . . . . C23 C 0.9474(4) 0.5757(3) 0.2901(3) 0.0688(9) Uani 1 1 d . . . . . C24 C 0.8988(5) 0.4659(3) 0.3375(3) 0.0703(9) Uani 1 1 d . . . . . H24 H 0.884102 0.440065 0.402411 0.084 Uiso 1 1 calc R . . . . C25 C 0.2005(5) -0.0470(3) 0.5925(2) 0.0714(10) Uani 1 1 d . . . . . H25A H 0.286846 -0.099586 0.637655 0.086 Uiso 1 1 calc R . . . . H25B H 0.091271 -0.057533 0.621535 0.086 Uiso 1 1 calc R . . . . C26 C 0.5197(5) 0.3327(3) -0.2074(3) 0.0804(11) Uani 1 1 d . . . . . H26A H 0.519306 0.412934 -0.254145 0.121 Uiso 1 1 calc GR . . . . H26B H 0.409941 0.333663 -0.177417 0.121 Uiso 1 1 calc GR . . . . H26C H 0.547641 0.270642 -0.236570 0.121 Uiso 1 1 calc GR . . . . C27 C 0.9781(7) 0.6534(5) 0.3433(4) 0.1161(17) Uani 1 1 d . . . . . H27A H 1.091726 0.663546 0.330774 0.174 Uiso 1 1 calc GR . . . . H27B H 0.961740 0.612154 0.409374 0.174 Uiso 1 1 calc GR . . . . H27C H 0.900414 0.733582 0.323367 0.174 Uiso 1 1 calc GR . . . . C30 C 0.574800 0.463981 0.531469 0.094(3) Uani 0.3333 1 d D U P A -2 H30A H 0.501770 0.521310 0.481620 0.141 Uiso 0.3333 1 d R . P A -2 H30B H 0.682250 0.484960 0.522070 0.141 Uiso 0.3333 1 d R . P A -2 H30C H 0.525020 0.468780 0.590470 0.141 Uiso 0.3333 1 d R . P A -2 O9 O 0.600440 0.338861 0.533400 0.133(4) Uani 0.3333 1 d D U P A -2 H9 H 0.709440 0.289990 0.557230 0.199 Uiso 0.3333 1 d R . P A -2 O10 O 0.626161 0.518391 0.548170 0.116(3) Uani 0.3333 1 d D U P B -1 H10 H 0.685020 0.432150 0.569790 0.173 Uiso 0.3333 1 d R . P B -1 C29 C 0.483469 0.533680 0.498700 0.130(5) Uani 0.3333 1 d D U P B -1 H29A H 0.517130 0.499200 0.449660 0.195 Uiso 0.3333 1 d R . P B -1 H29B H 0.431750 0.620900 0.471730 0.195 Uiso 0.3333 1 d R . P B -1 H29C H 0.404130 0.492010 0.540850 0.195 Uiso 0.3333 1 d R . P B -1 C28 C 0.455850 0.447160 0.494529 0.146(5) Uani 0.3333 1 d D U P C -3 H28A H 0.462890 0.454220 0.429750 0.219 Uiso 0.3333 1 d R . P C -3 H28B H 0.520450 0.498740 0.503070 0.219 Uiso 0.3333 1 d R . P C -3 H28C H 0.340030 0.473640 0.512540 0.219 Uiso 0.3333 1 d R . P C -3 O8 O 0.512589 0.321051 0.557080 0.157(4) Uani 0.3333 1 d D U P C -3 H8 H 0.601230 0.316110 0.594780 0.235 Uiso 0.3333 1 d R . P C -3 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 0.0317(3) 0.0374(3) 0.0413(4) -0.0069(3) -0.0003(3) -0.0068(2) N1 0.0284(9) 0.0311(10) 0.0355(11) -0.0085(9) 0.0000(8) -0.0051(8) O1 0.0380(10) 0.0557(12) 0.0618(13) -0.0267(11) 0.0097(9) -0.0105(9) O2 0.0537(12) 0.0512(12) 0.0542(13) -0.0002(10) -0.0168(10) -0.0080(9) O3 0.0676(13) 0.0537(12) 0.0491(13) -0.0183(11) 0.0210(10) 0.0004(10) O4 0.117(2) 0.0665(15) 0.0406(13) -0.0183(12) 0.0223(12) -0.0215(14) C1 0.0277(11) 0.0340(12) 0.0386(14) -0.0112(11) -0.0011(10) -0.0064(9) C2 0.0322(12) 0.0378(13) 0.0360(14) -0.0085(11) 0.0009(10) -0.0076(10) C3 0.0304(12) 0.0333(12) 0.0384(14) -0.0136(11) -0.0011(10) -0.0060(9) O5 0.0404(10) 0.0408(10) 0.0463(11) -0.0071(9) -0.0002(8) -0.0145(8) C4 0.0580(17) 0.0434(15) 0.0419(16) -0.0141(13) 0.0065(13) -0.0166(13) O6 0.0578(11) 0.0385(10) 0.0415(11) -0.0054(9) 0.0070(9) -0.0132(9) O7 0.119(2) 0.0570(14) 0.0439(13) -0.0116(11) 0.0274(13) -0.0336(13) C5 0.0314(12) 0.0324(12) 0.0376(14) -0.0102(11) 0.0015(10) -0.0089(9) C6 0.0480(15) 0.0317(13) 0.0431(15) -0.0092(12) -0.0022(12) -0.0064(11) C7 0.0371(12) 0.0332(13) 0.0352(14) -0.0072(11) 0.0018(10) -0.0036(10) C1AA 0.0387(13) 0.0466(15) 0.0432(15) -0.0190(13) 0.0079(11) -0.0100(11) C2AA 0.0298(12) 0.0352(13) 0.0485(16) -0.0100(12) 0.0023(11) -0.0037(10) C0AA 0.0469(14) 0.0311(13) 0.0394(15) -0.0078(11) 0.0005(11) -0.0073(11) C11 0.0364(12) 0.0344(13) 0.0420(15) -0.0113(12) 0.0028(11) -0.0080(10) C12 0.0384(13) 0.0402(14) 0.0417(15) -0.0153(12) 0.0019(11) -0.0041(11) C13 0.0379(13) 0.0291(12) 0.0483(16) -0.0129(12) 0.0073(11) -0.0015(10) C14 0.0419(14) 0.0392(14) 0.0507(17) -0.0219(13) 0.0004(12) 0.0000(11) C15 0.0585(17) 0.0462(16) 0.0389(16) -0.0068(13) 0.0063(13) -0.0143(13) C16 0.0676(19) 0.0485(17) 0.0449(17) -0.0207(15) 0.0047(14) -0.0107(14) C17 0.0494(15) 0.0390(14) 0.0489(17) -0.0189(13) 0.0076(12) -0.0092(12) C18 0.0394(14) 0.0379(14) 0.0606(19) -0.0119(14) 0.0067(12) -0.0055(11) C19 0.0638(18) 0.0454(16) 0.0511(18) -0.0127(14) 0.0034(14) -0.0197(14) C20 0.0480(16) 0.0625(19) 0.061(2) -0.0348(17) 0.0167(14) -0.0115(14) C21 0.0611(17) 0.0544(18) 0.0372(16) -0.0155(14) 0.0057(13) -0.0096(14) C22 0.0465(16) 0.0391(16) 0.096(3) -0.0210(18) 0.0080(16) -0.0117(13) C23 0.065(2) 0.063(2) 0.090(3) -0.038(2) 0.0087(19) -0.0234(17) C24 0.088(2) 0.069(2) 0.061(2) -0.0270(19) 0.0068(18) -0.0285(19) C25 0.095(3) 0.068(2) 0.0410(18) -0.0117(17) 0.0155(17) -0.0197(19) C26 0.092(3) 0.062(2) 0.073(3) -0.0011(19) -0.028(2) -0.0150(19) C27 0.153(4) 0.107(4) 0.132(4) -0.074(4) 0.014(3) -0.064(3) C30 0.111(7) 0.090(6) 0.111(7) -0.044(6) -0.028(6) -0.049(6) O9 0.129(7) 0.099(6) 0.175(8) -0.056(6) 0.038(6) -0.041(5) O10 0.153(8) 0.079(5) 0.116(7) -0.041(5) -0.021(6) -0.012(5) C29 0.128(9) 0.103(9) 0.156(9) -0.042(8) 0.039(8) -0.047(8) C28 0.161(10) 0.115(8) 0.171(9) -0.064(8) 0.004(8) -0.031(8) O8 0.187(9) 0.122(7) 0.175(8) -0.068(7) -0.041(7) -0.019(7) 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 O1 S1 O5 112.37(11) O1 S1 C2AA 105.89(11) O2 S1 O1 113.98(13) O2 S1 O5 111.87(11) O2 S1 C2AA 105.89(12) O5 S1 C2AA 106.11(12) C5 N1 H1 108.0 C5 N1 C7 110.48(18) C7 N1 H1 108.0 C13 N1 H1 108.0 C13 N1 C5 111.79(18) C13 N1 C7 110.43(18) C1AA O3 C20 116.9(2) C21 O4 C25 105.7(2) C3 C1 C7 121.6(2) C3 C1 C11 120.5(2) C11 C1 C7 117.8(2) C4 C2 C5 118.0(2) C12 C2 C4 119.7(2) C12 C2 C5 122.4(2) C1 C3 C0AA 120.9(2) C6 C3 C1 118.5(2) C6 C3 C0AA 120.6(2) C2 C4 H4 120.9 C15 C4 C2 118.2(3) C15 C4 H4 120.9 C11 O6 C26 114.8(2) C15 O7 C25 105.3(2) N1 C5 C2 112.31(19) N1 C5 H5 107.9 N1 C5 C0AA 107.55(19) C2 C5 H5 107.9 C2 C5 C0AA 113.1(2) C0AA C5 H5 107.9 C3 C6 H6 119.1 C14 C6 C3 121.7(2) C14 C6 H6 119.1 N1 C7 C1 110.69(19) N1 C7 H7A 109.5 N1 C7 H7B 109.5 C1 C7 H7A 109.5 C1 C7 H7B 109.5 H7A C7 H7B 108.1 O3 C1AA C11 115.6(2) O3 C1AA C14 124.9(2) C14 C1AA C11 119.5(2) C18 C2AA S1 118.8(2) C19 C2AA S1 121.2(2) C19 C2AA C18 120.0(3) C3 C0AA C5 113.8(2) C3 C0AA H0AA 108.8 C3 C0AA H0AB 108.8 C5 C0AA H0AA 108.8 C5 C0AA H0AB 108.8 H0AA C0AA H0AB 107.7 C1 C11 C1AA 120.1(2) O6 C11 C1 119.6(2) O6 C11 C1AA 120.2(2) C2 C12 C16 120.5(3) C2 C12 C17 120.3(2) C16 C12 C17 119.2(2) N1 C13 H13A 109.8 N1 C13 H13B 109.8 N1 C13 C17 109.2(2) H13A C13 H13B 108.3 C17 C13 H13A 109.8 C17 C13 H13B 109.8 C6 C14 C1AA 119.6(2) C6 C14 H14 120.2 C1AA C14 H14 120.2 C4 C15 O7 128.0(3) C4 C15 C21 121.6(3) O7 C15 C21 110.4(3) C12 C16 H16 120.7 C21 C16 C12 118.5(3) C21 C16 H16 120.7 C12 C17 H17A 109.1 C12 C17 H17B 109.1 C13 C17 C12 112.3(2) C13 C17 H17A 109.1 C13 C17 H17B 109.1 H17A C17 H17B 107.9 C2AA C18 H18 120.3 C22 C18 C2AA 119.5(3) C22 C18 H18 120.3 C2AA C19 H19 120.3 C2AA C19 C24 119.4(3) C24 C19 H19 120.3 O3 C20 H20A 109.5 O3 C20 H20B 109.5 O3 C20 H20C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C15 C21 O4 109.4(3) C16 C21 O4 129.2(3) C16 C21 C15 121.5(3) C18 C22 H22 119.2 C23 C22 C18 121.6(3) C23 C22 H22 119.2 C22 C23 C24 118.4(3) C22 C23 C27 121.1(4) C24 C23 C27 120.5(4) C19 C24 H24 119.4 C23 C24 C19 121.2(3) C23 C24 H24 119.4 O4 C25 H25A 109.9 O4 C25 H25B 109.9 O7 C25 O4 108.7(3) O7 C25 H25A 109.9 O7 C25 H25B 109.9 H25A C25 H25B 108.3 O6 C26 H26A 109.5 O6 C26 H26B 109.5 O6 C26 H26C 109.5 H26A C26 H26B 109.5 H26A C26 H26C 109.5 H26B C26 H26C 109.5 C23 C27 H27A 109.5 C23 C27 H27B 109.5 C23 C27 H27C 109.5 H27A C27 H27B 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 H30A C30 H30B 109.5 H30A C30 H30C 109.5 H30B C30 H30C 109.5 O9 C30 H30A 110.7 O9 C30 H30B 108.7 O9 C30 H30C 109.0 C30 O9 H9 110.7 C29 O10 H10 109.4 O10 C29 H29A 109.7 O10 C29 H29B 109.0 O10 C29 H29C 109.7 H29A C29 H29B 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 H28A C28 H28B 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 O8 C28 H28A 113.0 O8 C28 H28B 109.8 O8 C28 H28C 105.6 C28 O8 H8 109.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.4422(18) S1 O2 1.4370(19) S1 O5 1.4675(19) S1 C2AA 1.768(3) N1 H1 0.9800 N1 C5 1.492(3) N1 C7 1.494(3) N1 C13 1.487(3) O3 C1AA 1.367(3) O3 C20 1.422(3) O4 C21 1.373(4) O4 C25 1.422(4) C1 C3 1.387(3) C1 C7 1.499(3) C1 C11 1.388(3) C2 C4 1.407(4) C2 C5 1.506(3) C2 C12 1.388(3) C3 C6 1.385(3) C3 C0AA 1.498(4) C4 H4 0.9300 C4 C15 1.364(4) O6 C11 1.371(3) O6 C26 1.408(4) O7 C15 1.372(4) O7 C25 1.416(4) C5 H5 0.9800 C5 C0AA 1.528(3) C6 H6 0.9300 C6 C14 1.382(4) C7 H7A 0.9700 C7 H7B 0.9700 C1AA C11 1.395(3) C1AA C14 1.383(4) C2AA C18 1.385(4) C2AA C19 1.372(4) C0AA H0AA 0.9700 C0AA H0AB 0.9700 C12 C16 1.398(4) C12 C17 1.500(4) C13 H13A 0.9700 C13 H13B 0.9700 C13 C17 1.499(4) C14 H14 0.9300 C15 C21 1.373(4) C16 H16 0.9300 C16 C21 1.353(4) C17 H17A 0.9700 C17 H17B 0.9700 C18 H18 0.9300 C18 C22 1.384(4) C19 H19 0.9300 C19 C24 1.398(4) C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C22 H22 0.9300 C22 C23 1.369(5) C23 C24 1.379(5) C23 C27 1.515(5) C24 H24 0.9300 C25 H25A 0.9700 C25 H25B 0.9700 C26 H26A 0.9600 C26 H26B 0.9600 C26 H26C 0.9600 C27 H27A 0.9600 C27 H27B 0.9600 C27 H27C 0.9600 C30 H30A 0.9600 C30 H30B 0.9600 C30 H30C 0.9601 C30 O9 1.43430(13) O9 H9 0.9600 O10 H10 0.9600 O10 C29 1.40840(10) C29 H29A 0.9601 C29 H29B 0.9599 C29 H29C 0.9600 C28 H28A 0.9600 C28 H28B 0.9600 C28 H28C 0.9600 C28 O8 1.43854(18) O8 H8 0.9601 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 S1 C2AA C18 C22 -178.66(19) S1 C2AA C19 C24 179.0(2) N1 C5 C0AA C3 -46.0(3) N1 C13 C17 C12 -51.9(3) O1 S1 C2AA C18 68.7(2) O1 S1 C2AA C19 -109.6(2) O2 S1 C2AA C18 -52.7(2) O2 S1 C2AA C19 129.1(2) O3 C1AA C11 C1 180.0(2) O3 C1AA C11 O6 -3.1(3) O3 C1AA C14 C6 -179.5(2) C1 C3 C6 C14 0.4(4) C1 C3 C0AA C5 14.7(3) C2 C4 C15 O7 178.8(3) C2 C4 C15 C21 0.2(4) C2 C5 C0AA C3 -170.6(2) C2 C12 C16 C21 0.0(4) C2 C12 C17 C13 20.6(3) C3 C1 C7 N1 21.4(3) C3 C1 C11 O6 -177.5(2) C3 C1 C11 C1AA -0.5(4) C3 C6 C14 C1AA -0.3(4) O5 S1 C2AA C18 -171.74(18) O5 S1 C2AA C19 10.1(2) C4 C2 C5 N1 -170.1(2) C4 C2 C5 C0AA -48.1(3) C4 C2 C12 C16 1.4(4) C4 C2 C12 C17 -178.5(2) C4 C15 C21 O4 179.6(3) C4 C15 C21 C16 1.2(5) O7 C15 C21 O4 0.8(3) O7 C15 C21 C16 -177.6(3) C5 N1 C7 C1 -54.8(2) C5 N1 C13 C17 65.3(3) C5 C2 C4 C15 -179.9(2) C5 C2 C12 C16 179.7(2) C5 C2 C12 C17 -0.1(3) C6 C3 C0AA C5 -167.6(2) C7 N1 C5 C2 -167.26(18) C7 N1 C5 C0AA 67.6(2) C7 N1 C13 C17 -171.2(2) C7 C1 C3 C6 -179.7(2) C7 C1 C3 C0AA -1.9(3) C7 C1 C11 O6 2.2(3) C7 C1 C11 C1AA 179.2(2) C2AA C18 C22 C23 -0.3(4) C2AA C19 C24 C23 -0.6(5) C0AA C3 C6 C14 -177.4(2) C11 C1 C3 C6 0.1(3) C11 C1 C3 C0AA 177.8(2) C11 C1 C7 N1 -158.3(2) C11 C1AA C14 C6 -0.2(4) C12 C2 C4 C15 -1.4(4) C12 C2 C5 N1 11.5(3) C12 C2 C5 C0AA 133.5(2) C12 C16 C21 O4 -179.3(3) C12 C16 C21 C15 -1.3(4) C13 N1 C5 C2 -43.9(2) C13 N1 C5 C0AA -168.96(19) C13 N1 C7 C1 -178.99(19) C14 C1AA C11 C1 0.6(4) C14 C1AA C11 O6 177.5(2) C15 O7 C25 O4 7.8(4) C16 C12 C17 C13 -159.2(2) C17 C12 C16 C21 179.8(2) C18 C2AA C19 C24 0.9(4) C18 C22 C23 C24 0.6(5) C18 C22 C23 C27 180.0(3) C19 C2AA C18 C22 -0.4(4) C20 O3 C1AA C11 165.9(2) C20 O3 C1AA C14 -14.8(4) C21 O4 C25 O7 -7.4(4) C22 C23 C24 C19 -0.2(5) C25 O4 C21 C15 4.1(4) C25 O4 C21 C16 -177.7(3) C25 O7 C15 C4 176.0(3) C25 O7 C15 C21 -5.3(3) C26 O6 C11 C1 -102.3(3) C26 O6 C11 C1AA 80.7(3) C27 C23 C24 C19 -179.5(3)