#------------------------------------------------------------------------------ #$Date: 2024-10-13 03:22:13 +0300 (Sun, 13 Oct 2024) $ #$Revision: 295470 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160179.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_7160179 loop_ _publ_author_name 'Jastrzębska, Katarzyna' 'Antończyk, Patrycja' 'Dolot, Rafał' _publ_section_title ; P-Stereodefined morpholino dinucleoside 3',5'-phosphorothioates. ; _journal_name_full 'Organic & biomolecular chemistry' _journal_paper_doi 10.1039/d4ob01437e _journal_year 2024 _chemical_absolute_configuration ad _chemical_compound_source synthetic _chemical_formula_moiety 'C16 H24 N3 O5 P S2' _chemical_formula_sum 'C16 H24 N3 O5 P S2' _chemical_formula_weight 433.47 _chemical_name_systematic (R)-2-(uracil-1-yl)-(SP)-N-(2-thio-4,4-pentamethylene-1,3,2-oxathiaphospholane-2-yl)-(S)-6-hydroxymethyl-morpholine _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2024-07-12 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-07-12 deposited with the CCDC. 2024-10-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.4520(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.80030(10) _cell_length_b 28.6550(3) _cell_length_c 10.60610(10) _cell_measurement_reflns_used 11272 _cell_measurement_temperature 293.88(10) _cell_measurement_theta_max 76.0000 _cell_measurement_theta_min 3.0600 _cell_volume 2062.98(4) _computing_cell_refinement 'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293.88(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.949 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 103.00 128.00 0.50 0.70 -- 107.66 15.00 30.00 50 2 \w 101.00 133.00 0.50 0.70 -- 107.66 15.00 60.00 64 3 \w 101.00 131.00 0.50 0.70 -- 107.66 15.00 -30.00 60 4 \w 104.00 135.00 0.50 0.70 -- 107.66 15.00 -90.00 62 5 \w 103.00 135.00 0.50 0.70 -- 107.66 15.00-120.00 64 6 \w 102.00 136.00 0.50 0.70 -- 107.66 15.00-150.00 68 7 \w 101.00 126.00 0.50 0.70 -- 107.66 15.00-180.00 50 8 \w -19.00 29.00 0.50 0.18 -- -45.53 38.00 120.00 96 9 \w -9.00 29.00 0.50 0.18 -- -45.53 38.00 150.00 76 10 \w -18.00 30.00 0.50 0.18 -- -45.53 38.00 60.00 96 11 \w -50.00 -20.00 0.50 0.70 -- -93.75 61.00 150.00 60 12 \w -72.00 -26.00 0.50 0.70 -- -93.75 77.00 60.00 92 13 \w -51.00 -26.00 0.50 0.70 -- -93.75 61.00 30.00 50 14 \w -51.00 -23.00 0.50 0.70 -- -93.75 61.00-180.00 56 15 \w -154.00-103.00 0.50 0.70 -- -93.75 -77.00 -90.00 102 16 \w -144.00-102.00 0.50 0.70 -- -93.75 -88.00 139.00 84 17 \w -67.00 -27.00 0.50 0.70 -- -93.75 88.00-104.00 80 18 \w -51.00 8.00 0.50 0.18 -- -45.53 88.00-104.00 118 19 \w -76.00 -31.00 0.50 0.18 -- -45.53 125.00 0.00 90 20 \w 40.00 71.00 0.50 0.70 -- 107.66 -77.00-150.00 62 21 \w 65.00 92.00 0.50 0.70 -- 107.66 -95.00-180.00 54 22 \w 35.00 91.00 0.50 0.70 -- 107.66 -95.00-150.00 112 23 \w 40.00 65.00 0.50 0.18 -- 45.53 -88.00 139.00 50 24 \w 36.00 87.00 0.50 0.70 -- 107.66-125.00 120.00 102 25 \w 46.00 84.00 0.50 0.70 -- 107.66 -88.00 139.00 76 26 \w 134.00 160.00 0.50 0.70 -- 107.66 88.00-104.00 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0680598000 _diffrn_orient_matrix_UB_12 -0.0465219000 _diffrn_orient_matrix_UB_13 0.0558724000 _diffrn_orient_matrix_UB_21 -0.0867221000 _diffrn_orient_matrix_UB_22 -0.0149471000 _diffrn_orient_matrix_UB_23 -0.1313468000 _diffrn_orient_matrix_UB_31 0.1983564000 _diffrn_orient_matrix_UB_32 -0.0224562000 _diffrn_orient_matrix_UB_33 -0.0282085000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_unetI/netI 0.0319 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.949 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 12241 _diffrn_reflns_point_group_measured_fraction_full 0.821 _diffrn_reflns_point_group_measured_fraction_max 0.761 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.114 _diffrn_reflns_theta_min 3.084 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.357 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.29204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.100a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.396 _exptl_crystal_description prism _exptl_crystal_F_000 912 _exptl_crystal_recrystallization_method 'Crystallization from the mixture of acetonitrile : methanol (1:1 v/v)' _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.57 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.498 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.063 _refine_ls_abs_structure_details ; Flack x determined using 2257 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.001(19) _refine_ls_extinction_coef 0.0018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 498 _refine_ls_number_reflns 6583 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0486 _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^)+(0.0989P)^2^+0.5314P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1313 _refine_ls_wR_factor_ref 0.1319 _reflns_Friedel_coverage 0.570 _reflns_Friedel_fraction_full 0.637 _reflns_Friedel_fraction_max 0.564 _reflns_number_gt 6454 _reflns_number_total 6583 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01437e2.cif _cod_data_source_block kjmu_02 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7160179 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H N O P S' _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 0.453 _shelx_estimated_absorpt_t_min 0.251 _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 O(H) groups 2.a Ternary CH refined with riding coordinates: C6A(H6A), C6B(H6B), C2A(H2A), C2B(H2B) 2.b Secondary CH2 refined with riding coordinates: C3B(H3BA,H3BB), C3A(H3AA,H3AB), C13A(H13A,H13B), C5A(H5AA,H5AB), C16A(H16A, H16B), C5B(H5BA,H5BB), C14A(H14A,H14B), C16B(H16C,H16D), C14B(H14C,H14D), C17A(H17A,H17B), C17B(H17C,H17D), C19B(H19C,H19D), C20A(H20A,H20B), C18B(H18C, H18D), C20B(H20C,H20D), C18A(H18A,H18B), C19A(H19A,H19B) 2.c Aromatic/amide H refined with riding coordinates: N9B(H9B), N9A(H9A), C12A(H12A), C11A(H11A), C11B(H11B), C12B(H12B) 2.d Idealised tetrahedral OH refined as rotating group: O5A(H5A), O5B(H5B) ; _shelx_res_file ; TITL kjmu_02_a.res in P2(1) kjmu_02.res created by SHELXL-2018/3 at 08:39:33 on 12-Jul-2024 REM Old TITL kjmu_02 in P2(1) REM SHELXT solution in P2(1): R1 0.115, Rweak 0.038, Alpha 0.003 REM 3.437 for 16 systematic absences, Orientation as input REM Flack x = 0.103 ( 0.014 ) from 2288 Parsons' quotients REM Formula found by SHELXT: C6B N9A O3B S2A CELL 1.54184 6.8003 28.655 10.6061 90 93.452 90 ZERR 4 0.0001 0.0003 0.0001 0 0.001 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O P S UNIT 64 96 12 20 4 8 EQIV $1 +X,+Y,1+Z EQIV $2 +X,+Y,-1+Z EQIV $3 -1+X,+Y,+Z L.S. 6 PLAN 8 SIZE 0.57 0.57 0.28 TEMP 20.73(10) CONF HTAB O5A O3A_$1 HTAB O5B O3B_$2 HTAB N9B O5A_$3 HTAB N9A O5B MORE -1 BOND $H fmap 2 ACTA REM REM REM WGHT 0.098900 0.531400 EXTI 0.001823 FVAR 4.41221 P1A 5 0.679474 0.323723 1.021318 11.00000 0.05117 0.03473 = 0.03703 0.00186 0.00138 -0.00554 P1B 5 0.120015 0.675920 0.465528 11.00000 0.05131 0.03426 = 0.03978 -0.00057 0.00760 0.00236 S1B 6 -0.012986 0.643060 0.305919 11.00000 0.05757 0.04315 = 0.04391 0.00130 0.00601 -0.00839 S1A 6 0.561283 0.355775 1.177098 11.00000 0.05751 0.04729 = 0.04282 0.00378 0.00422 0.01113 S2B 6 -0.052362 0.688159 0.599115 11.00000 0.06355 0.08141 = 0.05109 -0.01090 0.01391 0.01677 S2A 6 0.492743 0.309074 0.883777 11.00000 0.07114 0.08547 = 0.04870 -0.00393 -0.00549 -0.03310 O1A 4 1.043737 0.439628 0.939241 11.00000 0.03953 0.04826 = 0.02894 0.00363 -0.00292 -0.00363 O2A 4 0.607218 0.448818 0.679438 11.00000 0.02851 0.07196 = 0.04784 0.01750 -0.00024 -0.00441 O1B 4 0.503207 0.561614 0.551424 11.00000 0.04299 0.04841 = 0.03033 0.00270 0.00937 0.00229 O5A 4 1.139931 0.496558 1.149954 11.00000 0.07092 0.04838 = 0.03200 0.00019 0.01219 -0.00866 AFIX 147 H5A 2 1.098839 0.505053 1.217354 11.00000 -1.50000 AFIX 0 O5B 4 0.550370 0.505126 0.342131 11.00000 0.06330 0.04908 = 0.02950 0.00033 0.00077 0.00199 AFIX 147 H5B 2 0.586421 0.493094 0.277277 11.00000 -1.50000 AFIX 0 O2B 4 0.124740 0.553579 0.817265 11.00000 0.03336 0.07316 = 0.05472 0.01907 0.01330 0.00827 O4A 4 0.775497 0.280049 1.098344 11.00000 0.09067 0.03021 = 0.05037 0.00455 0.01236 0.01027 O4B 4 0.197247 0.720351 0.392889 11.00000 0.08919 0.03055 = 0.05741 0.00044 0.00258 -0.00751 N7A 3 0.936288 0.441515 0.729248 11.00000 0.03223 0.05058 = 0.02911 0.00443 0.00129 -0.00054 O3A 4 1.025558 0.503216 0.398127 11.00000 0.05965 0.09286 = 0.04035 0.02041 0.01428 -0.00322 N9B 3 0.369735 0.527089 0.953469 11.00000 0.03953 0.05565 = 0.03659 0.01149 0.01608 0.00454 AFIX 43 H9B 2 0.284804 0.519837 1.007079 11.00000 -1.20000 AFIX 0 O3B 4 0.605033 0.495222 1.086124 11.00000 0.05953 0.08102 = 0.03784 0.01159 0.00933 0.01995 N4A 3 0.873550 0.351927 0.978200 11.00000 0.04922 0.04959 = 0.03730 0.00903 -0.00401 -0.00820 N7B 3 0.441289 0.560036 0.761525 11.00000 0.03609 0.04970 = 0.03131 0.00213 0.00958 -0.00320 C8A 1 0.774446 0.454543 0.651063 11.00000 0.03225 0.04497 = 0.03262 0.00549 -0.00197 -0.00338 N4B 3 0.323656 0.649435 0.513013 11.00000 0.05075 0.05174 = 0.04234 0.00822 0.00997 0.00562 N9A 3 0.821769 0.474834 0.538936 11.00000 0.03380 0.05367 = 0.03299 0.00846 -0.00229 -0.00187 AFIX 43 H9A 2 0.724565 0.483675 0.488988 11.00000 -1.20000 AFIX 0 C6A 1 1.010638 0.423910 1.066223 11.00000 0.04064 0.04753 = 0.03146 0.00554 0.00006 0.00034 AFIX 13 H6A 2 0.880062 0.434219 1.089079 11.00000 -1.20000 AFIX 0 C8B 1 0.296071 0.547104 0.842446 11.00000 0.03480 0.04560 = 0.03868 0.00493 0.01334 0.00203 C12A 1 1.126362 0.446146 0.691225 11.00000 0.03256 0.05874 = 0.03494 -0.00161 -0.00069 0.00152 AFIX 43 H12A 2 1.230547 0.435701 0.744707 11.00000 -1.20000 AFIX 0 C10B 1 0.563743 0.517325 0.988679 11.00000 0.04374 0.04992 = 0.03138 -0.00409 0.00653 0.00693 C10A 1 1.009181 0.482572 0.497745 11.00000 0.04349 0.05220 = 0.03112 0.00015 0.00726 -0.00234 C11A 1 1.165661 0.465122 0.580213 11.00000 0.03099 0.06689 = 0.04043 -0.00201 0.00785 -0.00308 AFIX 43 H11A 2 1.295062 0.466934 0.556817 11.00000 -1.20000 AFIX 0 C3B 1 0.370755 0.631857 0.640786 11.00000 0.05058 0.05088 = 0.03931 0.00029 0.00451 0.00300 AFIX 23 H3BA 2 0.273360 0.642834 0.697022 11.00000 -1.20000 H3BB 2 0.498757 0.643409 0.671787 11.00000 -1.20000 AFIX 0 C3A 1 0.897437 0.369390 0.850552 11.00000 0.04736 0.05000 = 0.03545 0.00233 0.00340 -0.00598 AFIX 23 H3AA 2 0.790633 0.358120 0.793848 11.00000 -1.20000 H3AB 2 1.020625 0.358160 0.820269 11.00000 -1.20000 AFIX 0 C6B 1 0.446144 0.577198 0.425716 11.00000 0.04095 0.04975 = 0.03160 0.00452 0.00659 -0.00035 AFIX 13 H6B 2 0.310257 0.567421 0.403844 11.00000 -1.20000 AFIX 0 C13A 1 1.166319 0.447491 1.151590 11.00000 0.05348 0.05071 = 0.03585 0.00487 -0.00726 -0.00615 AFIX 23 H13A 2 1.158657 0.436008 1.237188 11.00000 -1.20000 H13B 2 1.295816 0.439943 1.123734 11.00000 -1.20000 AFIX 0 C11B 1 0.702578 0.534542 0.904012 11.00000 0.03556 0.06386 = 0.03622 -0.00395 0.00120 0.00262 AFIX 43 H11B 2 0.837076 0.532057 0.924501 11.00000 -1.20000 AFIX 0 C2A 1 0.896887 0.421931 0.852610 11.00000 0.03014 0.04977 = 0.02873 0.00573 -0.00130 -0.00158 AFIX 13 H2A 2 0.767810 0.432841 0.876687 11.00000 -1.20000 AFIX 0 C5A 1 1.019930 0.371576 1.070954 11.00000 0.04164 0.05036 = 0.04528 0.01046 -0.00610 -0.00374 AFIX 23 H5AA 2 1.150736 0.361150 1.052290 11.00000 -1.20000 H5AB 2 0.993491 0.360828 1.154991 11.00000 -1.20000 AFIX 0 C12B 1 0.637408 0.554254 0.795080 11.00000 0.03554 0.06616 = 0.03279 -0.00435 0.00782 -0.01057 AFIX 43 H12B 2 0.729251 0.564479 0.739715 11.00000 -1.20000 AFIX 0 C2B 1 0.372434 0.578892 0.638865 11.00000 0.03477 0.04860 = 0.03121 0.00061 0.00665 -0.00181 AFIX 13 H2B 2 0.239189 0.567361 0.616552 11.00000 -1.20000 AFIX 0 C15A 1 0.601780 0.303810 1.281095 11.00000 0.06960 0.04253 = 0.04295 0.00779 0.00401 -0.00534 C16A 1 0.765878 0.313927 1.379640 11.00000 0.07958 0.05485 = 0.04654 0.01012 -0.00865 -0.00048 AFIX 23 H16A 2 0.881716 0.323983 1.337961 11.00000 -1.20000 H16B 2 0.799303 0.285487 1.425683 11.00000 -1.20000 AFIX 0 C5B 1 0.457897 0.630392 0.421639 11.00000 0.05292 0.04747 = 0.04233 0.00981 0.01428 0.00532 AFIX 23 H5BA 2 0.591765 0.640537 0.443321 11.00000 -1.20000 H5BB 2 0.419730 0.641511 0.337309 11.00000 -1.20000 AFIX 0 C13B 1 0.581800 0.553742 0.337642 11.00000 0.05965 0.05567 = 0.03616 0.00837 0.01406 0.00709 C15B 1 0.014633 0.694070 0.200550 11.00000 0.08375 0.03775 = 0.04476 0.00413 0.00133 0.00800 C14A 1 0.650424 0.264070 1.194173 11.00000 0.12009 0.03575 = 0.05472 0.00872 0.00927 -0.01438 AFIX 23 H14A 2 0.716417 0.239397 1.242946 11.00000 -1.20000 H14B 2 0.529649 0.251407 1.154596 11.00000 -1.20000 AFIX 0 C16B 1 0.178751 0.686089 0.113164 11.00000 0.08695 0.05424 = 0.05278 0.01201 0.01402 -0.00923 AFIX 23 H16C 2 0.297685 0.677630 0.163011 11.00000 -1.20000 H16D 2 0.204479 0.714963 0.069352 11.00000 -1.20000 AFIX 0 C14B 1 0.063828 0.735046 0.291047 11.00000 0.12008 0.03383 = 0.05848 0.00390 -0.00437 0.01006 AFIX 23 H14C 2 0.122818 0.760202 0.245163 11.00000 -1.20000 H14D 2 -0.056357 0.746710 0.324546 11.00000 -1.20000 AFIX 0 C17A 1 0.709475 0.351451 1.472507 11.00000 0.10380 0.07428 = 0.05313 -0.00648 -0.01217 -0.00009 AFIX 23 H17A 2 0.816508 0.355715 1.536130 11.00000 -1.20000 H17B 2 0.689091 0.380786 1.427989 11.00000 -1.20000 AFIX 0 C17B 1 0.131250 0.648216 0.016866 11.00000 0.11122 0.07677 = 0.05932 -0.00672 0.02693 -0.01043 AFIX 23 H17C 2 0.236797 0.646046 -0.040435 11.00000 -1.20000 H17D 2 0.121604 0.618450 0.059607 11.00000 -1.20000 AFIX 0 C19B 1 -0.227475 0.664712 0.028449 11.00000 0.10462 0.10914 = 0.07856 0.00720 -0.03418 -0.00248 AFIX 23 H19C 2 -0.251104 0.635611 0.071737 11.00000 -1.20000 H19D 2 -0.346470 0.672852 -0.021760 11.00000 -1.20000 AFIX 0 C20A 1 0.409795 0.292393 1.345260 11.00000 0.09145 0.09849 = 0.06385 0.00902 0.01437 -0.03977 AFIX 23 H20A 2 0.302839 0.289501 1.280985 11.00000 -1.20000 H20B 2 0.424581 0.262578 1.388091 11.00000 -1.20000 AFIX 0 C18B 1 -0.059798 0.658365 -0.057217 11.00000 0.14954 0.09149 = 0.05456 -0.00015 -0.00676 -0.02736 AFIX 23 H18C 2 -0.090439 0.632830 -0.115147 11.00000 -1.20000 H18D 2 -0.045323 0.686477 -0.106754 11.00000 -1.20000 AFIX 0 C20B 1 -0.179510 0.703259 0.126107 11.00000 0.10694 0.08903 = 0.08039 0.01362 -0.01384 0.03495 AFIX 23 H20C 2 -0.172468 0.733043 0.083150 11.00000 -1.20000 H20D 2 -0.284504 0.705088 0.183897 11.00000 -1.20000 AFIX 0 C18A 1 0.525793 0.338640 1.535577 11.00000 0.13201 0.10422 = 0.05156 -0.00662 0.01023 0.01406 AFIX 23 H18A 2 0.490654 0.363826 1.591039 11.00000 -1.20000 H18B 2 0.550270 0.310970 1.586824 11.00000 -1.20000 AFIX 0 C19A 1 0.356627 0.329434 1.440182 11.00000 0.09904 0.13455 = 0.07368 -0.00378 0.03422 -0.00811 AFIX 23 H19A 2 0.321706 0.358138 1.395815 11.00000 -1.20000 H19B 2 0.242873 0.319175 1.483704 11.00000 -1.20000 AFIX 0 H13C 2 0.553908 0.566484 0.250083 11.00000 0.04673 H13D 2 0.719576 0.554627 0.371144 11.00000 0.06196 HKLF 4 REM kjmu_02_a.res in P2(1) REM wR2 = 0.1319, GooF = S = 1.028, Restrained GooF = 1.027 for all data REM R1 = 0.0486 for 6454 Fo > 4sig(Fo) and 0.0491 for all 6583 data REM 498 parameters refined using 1 restraints END WGHT 0.0989 0.5314 REM Highest difference peak 0.498, deepest hole -0.399, 1-sigma level 0.063 Q1 1 0.5255 0.3112 0.9594 11.00000 0.05 0.50 Q2 1 0.6782 0.3595 1.2067 11.00000 0.05 0.44 Q3 1 0.6405 0.3205 0.9451 11.00000 0.05 0.43 Q4 1 0.6121 0.3583 1.2569 11.00000 0.05 0.39 Q5 1 0.6857 0.3274 1.1030 11.00000 0.05 0.38 Q6 1 0.1092 0.6709 0.3881 11.00000 0.05 0.34 Q7 1 -0.1382 0.6426 0.2430 11.00000 0.05 0.34 Q8 1 0.8925 0.3589 1.0444 11.00000 0.05 0.33 ; _shelx_res_checksum 41344 _olex2_exptl_crystal_mounting_method 'The crystal was glued to a support using the CA glue' _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.170 _oxdiff_exptl_absorpt_empirical_full_min 0.503 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1A P 0.67947(16) 0.32372(4) 1.02132(10) 0.0410(3) Uani 1 1 d . . . . . P1B P 0.12002(17) 0.67592(4) 0.46553(10) 0.0416(3) Uani 1 1 d . . . . . S1B S -0.01299(17) 0.64306(4) 0.30592(10) 0.0481(3) Uani 1 1 d . . . . . S1A S 0.56128(18) 0.35577(4) 1.17710(10) 0.0492(3) Uani 1 1 d . . . . . S2B S -0.0524(2) 0.68816(6) 0.59912(13) 0.0649(4) Uani 1 1 d . . . . . S2A S 0.4927(2) 0.30907(6) 0.88378(13) 0.0688(4) Uani 1 1 d . . . . . O1A O 1.0437(4) 0.43963(11) 0.9392(3) 0.0391(6) Uani 1 1 d . . . . . O2A O 0.6072(4) 0.44882(14) 0.6794(3) 0.0495(8) Uani 1 1 d . . . . . O1B O 0.5032(4) 0.56161(11) 0.5514(3) 0.0403(6) Uani 1 1 d . . . . . O5A O 1.1399(5) 0.49656(12) 1.1500(3) 0.0501(8) Uani 1 1 d . . . . . H5A H 1.098839 0.505053 1.217354 0.075 Uiso 1 1 calc R U . . . O5B O 0.5504(5) 0.50513(12) 0.3421(3) 0.0474(7) Uani 1 1 d . . . . . H5B H 0.586421 0.493094 0.277277 0.071 Uiso 1 1 calc R U . . . O2B O 0.1247(4) 0.55358(14) 0.8173(3) 0.0533(8) Uani 1 1 d . . . . . O4A O 0.7755(6) 0.28005(11) 1.0983(3) 0.0568(9) Uani 1 1 d . . . . . O4B O 0.1972(6) 0.72035(12) 0.3929(4) 0.0591(9) Uani 1 1 d . . . . . N7A N 0.9363(5) 0.44152(13) 0.7292(3) 0.0373(7) Uani 1 1 d . . . . . O3A O 1.0256(6) 0.50322(17) 0.3981(3) 0.0638(10) Uani 1 1 d . . . . . N9B N 0.3697(5) 0.52709(15) 0.9535(3) 0.0434(8) Uani 1 1 d . . . . . H9B H 0.284804 0.519837 1.007079 0.052 Uiso 1 1 calc R U . . . O3B O 0.6050(5) 0.49522(16) 1.0861(3) 0.0592(9) Uani 1 1 d . . . . . N4A N 0.8735(6) 0.35193(15) 0.9782(3) 0.0456(8) Uani 1 1 d . . . . . N7B N 0.4413(5) 0.56004(14) 0.7615(3) 0.0387(7) Uani 1 1 d . . . . . C8A C 0.7744(6) 0.45454(15) 0.6511(4) 0.0368(8) Uani 1 1 d . . . . . N4B N 0.3237(6) 0.64943(15) 0.5130(4) 0.0480(9) Uani 1 1 d . . . . . N9A N 0.8218(5) 0.47483(14) 0.5389(3) 0.0403(7) Uani 1 1 d . . . . . H9A H 0.724565 0.483675 0.488988 0.048 Uiso 1 1 calc R U . . . C6A C 1.0106(6) 0.42391(16) 1.0662(4) 0.0400(8) Uani 1 1 d . . . . . H6A H 0.880062 0.434219 1.089079 0.048 Uiso 1 1 calc R U . . . C8B C 0.2961(6) 0.54710(16) 0.8424(4) 0.0392(8) Uani 1 1 d . . . . . C12A C 1.1264(6) 0.44615(18) 0.6912(4) 0.0422(9) Uani 1 1 d . . . . . H12A H 1.230547 0.435701 0.744707 0.051 Uiso 1 1 calc R U . . . C10B C 0.5637(6) 0.51733(17) 0.9887(4) 0.0415(9) Uani 1 1 d . . . . . C10A C 1.0092(7) 0.48257(17) 0.4977(4) 0.0421(9) Uani 1 1 d . . . . . C11A C 1.1657(6) 0.46512(19) 0.5802(4) 0.0459(10) Uani 1 1 d . . . . . H11A H 1.295062 0.466934 0.556817 0.055 Uiso 1 1 calc R U . . . C3B C 0.3708(7) 0.63186(18) 0.6408(4) 0.0468(10) Uani 1 1 d . . . . . H3BA H 0.273360 0.642834 0.697022 0.056 Uiso 1 1 calc R U . . . H3BB H 0.498757 0.643409 0.671787 0.056 Uiso 1 1 calc R U . . . C3A C 0.8974(7) 0.36939(17) 0.8506(4) 0.0442(9) Uani 1 1 d . . . . . H3AA H 0.790633 0.358120 0.793848 0.053 Uiso 1 1 calc R U . . . H3AB H 1.020625 0.358160 0.820269 0.053 Uiso 1 1 calc R U . . . C6B C 0.4461(6) 0.57720(17) 0.4257(4) 0.0406(9) Uani 1 1 d . . . . . H6B H 0.310257 0.567421 0.403844 0.049 Uiso 1 1 calc R U . . . C13A C 1.1663(7) 0.44749(18) 1.1516(4) 0.0471(10) Uani 1 1 d . . . . . H13A H 1.158657 0.436008 1.237188 0.056 Uiso 1 1 calc R U . . . H13B H 1.295816 0.439943 1.123734 0.056 Uiso 1 1 calc R U . . . C11B C 0.7026(6) 0.53454(19) 0.9040(4) 0.0453(10) Uani 1 1 d . . . . . H11B H 0.837076 0.532057 0.924501 0.054 Uiso 1 1 calc R U . . . C2A C 0.8969(5) 0.42193(15) 0.8526(3) 0.0363(8) Uani 1 1 d . . . . . H2A H 0.767810 0.432841 0.876687 0.044 Uiso 1 1 calc R U . . . C5A C 1.0199(7) 0.37158(17) 1.0710(4) 0.0461(10) Uani 1 1 d . . . . . H5AA H 1.150736 0.361150 1.052290 0.055 Uiso 1 1 calc R U . . . H5AB H 0.993491 0.360828 1.154991 0.055 Uiso 1 1 calc R U . . . C12B C 0.6374(6) 0.55425(18) 0.7951(4) 0.0446(10) Uani 1 1 d . . . . . H12B H 0.729251 0.564479 0.739715 0.054 Uiso 1 1 calc R U . . . C2B C 0.3724(6) 0.57889(16) 0.6389(4) 0.0380(8) Uani 1 1 d . . . . . H2B H 0.239189 0.567361 0.616552 0.046 Uiso 1 1 calc R U . . . C15A C 0.6018(8) 0.30381(18) 1.2811(5) 0.0517(11) Uani 1 1 d . . . . . C16A C 0.7659(9) 0.3139(2) 1.3796(5) 0.0608(13) Uani 1 1 d . . . . . H16A H 0.881716 0.323983 1.337961 0.073 Uiso 1 1 calc R U . . . H16B H 0.799303 0.285487 1.425683 0.073 Uiso 1 1 calc R U . . . C5B C 0.4579(7) 0.63039(17) 0.4216(4) 0.0471(10) Uani 1 1 d . . . . . H5BA H 0.591765 0.640537 0.443321 0.057 Uiso 1 1 calc R U . . . H5BB H 0.419730 0.641511 0.337309 0.057 Uiso 1 1 calc R U . . . C13B C 0.5818(8) 0.55374(19) 0.3376(4) 0.0500(11) Uani 1 1 d . . . . . C15B C 0.0146(9) 0.69407(18) 0.2005(5) 0.0555(12) Uani 1 1 d . . . . . C14A C 0.6504(12) 0.26407(19) 1.1942(6) 0.0700(16) Uani 1 1 d . . . . . H14A H 0.716417 0.239397 1.242946 0.084 Uiso 1 1 calc R U . . . H14B H 0.529649 0.251407 1.154596 0.084 Uiso 1 1 calc R U . . . C16B C 0.1788(10) 0.6861(2) 0.1132(5) 0.0643(14) Uani 1 1 d . . . . . H16C H 0.297685 0.677630 0.163011 0.077 Uiso 1 1 calc R U . . . H16D H 0.204479 0.714963 0.069352 0.077 Uiso 1 1 calc R U . . . C14B C 0.0638(12) 0.73505(19) 0.2910(6) 0.0712(17) Uani 1 1 d . . . . . H14C H 0.122818 0.760202 0.245163 0.085 Uiso 1 1 calc R U . . . H14D H -0.056357 0.746710 0.324546 0.085 Uiso 1 1 calc R U . . . C17A C 0.7095(12) 0.3515(3) 1.4725(6) 0.0778(18) Uani 1 1 d . . . . . H17A H 0.816508 0.355715 1.536130 0.093 Uiso 1 1 calc R U . . . H17B H 0.689091 0.380786 1.427989 0.093 Uiso 1 1 calc R U . . . C17B C 0.1313(12) 0.6482(3) 0.0169(6) 0.0816(19) Uani 1 1 d . . . . . H17C H 0.236797 0.646046 -0.040435 0.098 Uiso 1 1 calc R U . . . H17D H 0.121604 0.618450 0.059607 0.098 Uiso 1 1 calc R U . . . C19B C -0.2275(14) 0.6647(4) 0.0284(8) 0.099(3) Uani 1 1 d . . . . . H19C H -0.251104 0.635611 0.071737 0.119 Uiso 1 1 calc R U . . . H19D H -0.346470 0.672852 -0.021760 0.119 Uiso 1 1 calc R U . . . C20A C 0.4098(12) 0.2924(3) 1.3453(7) 0.084(2) Uani 1 1 d . . . . . H20A H 0.302839 0.289501 1.280985 0.101 Uiso 1 1 calc R U . . . H20B H 0.424581 0.262578 1.388091 0.101 Uiso 1 1 calc R U . . . C18B C -0.0598(16) 0.6584(3) -0.0572(7) 0.099(3) Uani 1 1 d . . . . . H18C H -0.090439 0.632830 -0.115147 0.119 Uiso 1 1 calc R U . . . H18D H -0.045323 0.686477 -0.106754 0.119 Uiso 1 1 calc R U . . . C20B C -0.1795(13) 0.7033(3) 0.1261(8) 0.093(2) Uani 1 1 d . . . . . H20C H -0.172468 0.733043 0.083150 0.111 Uiso 1 1 calc R U . . . H20D H -0.284504 0.705088 0.183897 0.111 Uiso 1 1 calc R U . . . C18A C 0.5258(14) 0.3386(4) 1.5356(7) 0.096(2) Uani 1 1 d . . . . . H18A H 0.490654 0.363826 1.591039 0.115 Uiso 1 1 calc R U . . . H18B H 0.550270 0.310970 1.586824 0.115 Uiso 1 1 calc R U . . . C19A C 0.3566(13) 0.3294(4) 1.4402(7) 0.101(3) Uani 1 1 d . . . . . H19A H 0.321706 0.358138 1.395815 0.122 Uiso 1 1 calc R U . . . H19B H 0.242873 0.319175 1.483704 0.122 Uiso 1 1 calc R U . . . H13C H 0.554(8) 0.566(2) 0.250(5) 0.047(14) Uiso 1 1 d . . . . . H13D H 0.720(10) 0.555(2) 0.371(6) 0.062(17) Uiso 1 1 d . . . . . 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 P1A 0.0512(6) 0.0347(5) 0.0370(5) 0.0019(4) 0.0014(4) -0.0055(4) P1B 0.0513(6) 0.0343(5) 0.0398(5) -0.0006(4) 0.0076(4) 0.0024(4) S1B 0.0576(6) 0.0431(5) 0.0439(5) 0.0013(4) 0.0060(4) -0.0084(5) S1A 0.0575(6) 0.0473(6) 0.0428(5) 0.0038(4) 0.0042(4) 0.0111(5) S2B 0.0635(7) 0.0814(10) 0.0511(7) -0.0109(6) 0.0139(5) 0.0168(7) S2A 0.0711(8) 0.0855(10) 0.0487(6) -0.0039(6) -0.0055(5) -0.0331(7) O1A 0.0395(14) 0.0483(16) 0.0289(12) 0.0036(12) -0.0029(10) -0.0036(12) O2A 0.0285(13) 0.072(2) 0.0478(16) 0.0175(15) -0.0002(11) -0.0044(14) O1B 0.0430(14) 0.0484(16) 0.0303(13) 0.0027(12) 0.0094(11) 0.0023(12) O5A 0.071(2) 0.0484(17) 0.0320(14) 0.0002(13) 0.0122(14) -0.0087(15) O5B 0.0633(19) 0.0491(17) 0.0295(13) 0.0003(12) 0.0008(13) 0.0020(14) O2B 0.0334(14) 0.073(2) 0.0547(18) 0.0191(16) 0.0133(12) 0.0083(14) O4A 0.091(3) 0.0302(15) 0.0504(19) 0.0046(13) 0.0124(17) 0.0103(16) O4B 0.089(3) 0.0306(15) 0.057(2) 0.0004(14) 0.0026(18) -0.0075(16) N7A 0.0322(16) 0.051(2) 0.0291(15) 0.0044(14) 0.0013(12) -0.0005(14) O3A 0.060(2) 0.093(3) 0.0403(17) 0.0204(18) 0.0143(15) -0.003(2) N9B 0.0395(17) 0.056(2) 0.0366(17) 0.0115(16) 0.0161(13) 0.0045(16) O3B 0.060(2) 0.081(3) 0.0378(16) 0.0116(17) 0.0093(14) 0.0200(18) N4A 0.0492(19) 0.050(2) 0.0373(17) 0.0090(16) -0.0040(14) -0.0082(16) N7B 0.0361(16) 0.0497(19) 0.0313(16) 0.0021(14) 0.0096(13) -0.0032(14) C8A 0.0322(18) 0.045(2) 0.0326(18) 0.0055(16) -0.0020(14) -0.0034(15) N4B 0.051(2) 0.052(2) 0.0423(19) 0.0082(17) 0.0100(15) 0.0056(17) N9A 0.0338(16) 0.054(2) 0.0330(16) 0.0085(15) -0.0023(12) -0.0019(14) C6A 0.041(2) 0.048(2) 0.0315(18) 0.0055(17) 0.0001(14) 0.0003(17) C8B 0.0348(19) 0.046(2) 0.0387(19) 0.0049(17) 0.0133(15) 0.0020(16) C12A 0.0326(18) 0.059(3) 0.0349(19) -0.0016(18) -0.0007(15) 0.0015(18) C10B 0.044(2) 0.050(2) 0.0314(18) -0.0041(17) 0.0065(15) 0.0069(18) C10A 0.043(2) 0.052(2) 0.0311(18) 0.0001(17) 0.0073(15) -0.0023(18) C11A 0.0310(18) 0.067(3) 0.040(2) -0.002(2) 0.0079(15) -0.0031(19) C3B 0.051(2) 0.051(3) 0.039(2) 0.0003(18) 0.0045(17) 0.0030(19) C3A 0.047(2) 0.050(2) 0.035(2) 0.0023(18) 0.0034(17) -0.0060(18) C6B 0.041(2) 0.050(2) 0.0316(18) 0.0045(17) 0.0066(15) -0.0004(17) C13A 0.053(2) 0.051(2) 0.036(2) 0.0049(18) -0.0073(18) -0.006(2) C11B 0.0356(19) 0.064(3) 0.036(2) -0.0040(19) 0.0012(15) 0.0026(18) C2A 0.0301(17) 0.050(2) 0.0287(17) 0.0057(16) -0.0013(13) -0.0016(16) C5A 0.042(2) 0.050(2) 0.045(2) 0.0105(19) -0.0061(17) -0.0037(18) C12B 0.0355(19) 0.066(3) 0.0328(18) -0.0043(19) 0.0078(15) -0.0106(19) C2B 0.0348(18) 0.049(2) 0.0312(18) 0.0006(16) 0.0067(14) -0.0018(16) C15A 0.070(3) 0.043(2) 0.043(2) 0.0078(19) 0.004(2) -0.005(2) C16A 0.080(3) 0.055(3) 0.047(2) 0.010(2) -0.009(2) 0.000(3) C5B 0.053(2) 0.047(2) 0.042(2) 0.0098(18) 0.0143(18) 0.0053(19) C13B 0.060(3) 0.056(3) 0.036(2) 0.008(2) 0.0141(19) 0.007(2) C15B 0.084(3) 0.038(2) 0.045(2) 0.0041(19) 0.001(2) 0.008(2) C14A 0.120(5) 0.036(2) 0.055(3) 0.009(2) 0.009(3) -0.014(3) C16B 0.087(4) 0.054(3) 0.053(3) 0.012(2) 0.014(3) -0.009(3) C14B 0.120(5) 0.034(2) 0.058(3) 0.004(2) -0.004(3) 0.010(3) C17A 0.104(5) 0.074(4) 0.053(3) -0.006(3) -0.012(3) 0.000(4) C17B 0.111(5) 0.077(4) 0.059(3) -0.007(3) 0.027(3) -0.010(4) C19B 0.105(6) 0.109(7) 0.079(5) 0.007(4) -0.034(4) -0.002(5) C20A 0.091(5) 0.098(5) 0.064(4) 0.009(4) 0.014(3) -0.040(4) C18B 0.150(8) 0.091(6) 0.055(4) 0.000(3) -0.007(4) -0.027(5) C20B 0.107(6) 0.089(5) 0.080(5) 0.014(4) -0.014(4) 0.035(4) C18A 0.132(7) 0.104(6) 0.052(3) -0.007(3) 0.010(4) 0.014(5) C19A 0.099(5) 0.135(8) 0.074(4) -0.004(5) 0.034(4) -0.008(5) 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' 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' P P 0.2955 0.4335 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2A P1A S1A 115.31(8) . . ? O4A P1A S1A 95.96(14) . . ? O4A P1A S2A 116.38(16) . . ? O4A P1A N4A 102.5(2) . . ? N4A P1A S1A 111.01(16) . . ? N4A P1A S2A 113.76(14) . . ? S2B P1B S1B 115.11(8) . . ? O4B P1B S1B 96.16(15) . . ? O4B P1B S2B 116.32(17) . . ? O4B P1B N4B 102.9(2) . . ? N4B P1B S1B 110.95(16) . . ? N4B P1B S2B 113.62(15) . . ? C15B S1B P1B 94.48(17) . . ? C15A S1A P1A 93.81(17) . . ? C2A O1A C6A 110.5(3) . . ? C2B O1B C6B 110.8(3) . . ? C13A O5A H5A 109.5 . . ? C13B O5B H5B 109.5 . . ? C14A O4A P1A 111.5(4) . . ? C14B O4B P1B 112.8(4) . . ? C8A N7A C2A 117.1(3) . . ? C12A N7A C8A 121.4(3) . . ? C12A N7A C2A 121.5(3) . . ? C8B N9B H9B 116.2 . . ? C8B N9B C10B 127.6(3) . . ? C10B N9B H9B 116.2 . . ? C3A N4A P1A 124.4(3) . . ? C3A N4A C5A 112.4(4) . . ? C5A N4A P1A 121.8(3) . . ? C8B N7B C2B 116.4(3) . . ? C12B N7B C8B 121.4(4) . . ? C12B N7B C2B 122.1(3) . . ? O2A C8A N7A 122.7(4) . . ? O2A C8A N9A 123.1(4) . . ? N9A C8A N7A 114.2(3) . . ? C3B N4B P1B 125.5(3) . . ? C3B N4B C5B 111.8(4) . . ? C5B N4B P1B 121.1(3) . . ? C8A N9A H9A 116.4 . . ? C8A N9A C10A 127.2(3) . . ? C10A N9A H9A 116.4 . . ? O1A C6A H6A 109.2 . . ? O1A C6A C13A 106.0(3) . . ? O1A C6A C5A 109.4(4) . . ? C13A C6A H6A 109.2 . . ? C5A C6A H6A 109.2 . . ? C5A C6A C13A 113.6(4) . . ? O2B C8B N9B 123.8(4) . . ? O2B C8B N7B 122.5(4) . . ? N9B C8B N7B 113.7(3) . . ? N7A C12A H12A 118.8 . . ? C11A C12A N7A 122.3(4) . . ? C11A C12A H12A 118.8 . . ? N9B C10B C11B 114.7(4) . . ? O3B C10B N9B 119.9(4) . . ? O3B C10B C11B 125.4(4) . . ? O3A C10A N9A 118.8(4) . . ? O3A C10A C11A 126.6(4) . . ? N9A C10A C11A 114.6(4) . . ? C12A C11A C10A 120.0(4) . . ? C12A C11A H11A 120.0 . . ? C10A C11A H11A 120.0 . . ? N4B C3B H3BA 109.8 . . ? N4B C3B H3BB 109.8 . . ? N4B C3B C2B 109.5(4) . . ? H3BA C3B H3BB 108.2 . . ? C2B C3B H3BA 109.8 . . ? C2B C3B H3BB 109.8 . . ? N4A C3A H3AA 109.8 . . ? N4A C3A H3AB 109.8 . . ? N4A C3A C2A 109.2(4) . . ? H3AA C3A H3AB 108.3 . . ? C2A C3A H3AA 109.8 . . ? C2A C3A H3AB 109.8 . . ? O1B C6B H6B 109.2 . . ? O1B C6B C5B 109.0(4) . . ? O1B C6B C13B 107.1(4) . . ? C5B C6B H6B 109.2 . . ? C13B C6B H6B 109.2 . . ? C13B C6B C5B 113.1(4) . . ? O5A C13A C6A 110.7(4) . . ? O5A C13A H13A 109.5 . . ? O5A C13A H13B 109.5 . . ? C6A C13A H13A 109.5 . . ? C6A C13A H13B 109.5 . . ? H13A C13A H13B 108.1 . . ? C10B C11B H11B 120.3 . . ? C12B C11B C10B 119.4(4) . . ? C12B C11B H11B 120.3 . . ? O1A C2A N7A 106.5(3) . . ? O1A C2A C3A 111.5(3) . . ? O1A C2A H2A 109.0 . . ? N7A C2A C3A 111.7(3) . . ? N7A C2A H2A 109.0 . . ? C3A C2A H2A 109.0 . . ? N4A C5A C6A 109.6(4) . . ? N4A C5A H5AA 109.8 . . ? N4A C5A H5AB 109.8 . . ? C6A C5A H5AA 109.8 . . ? C6A C5A H5AB 109.8 . . ? H5AA C5A H5AB 108.2 . . ? N7B C12B H12B 118.6 . . ? C11B C12B N7B 122.8(4) . . ? C11B C12B H12B 118.6 . . ? O1B C2B N7B 105.9(3) . . ? O1B C2B C3B 111.4(3) . . ? O1B C2B H2B 109.4 . . ? N7B C2B C3B 111.1(4) . . ? N7B C2B H2B 109.4 . . ? C3B C2B H2B 109.4 . . ? C16A C15A S1A 109.4(4) . . ? C16A C15A C14A 112.7(5) . . ? C16A C15A C20A 110.2(5) . . ? C14A C15A S1A 105.7(3) . . ? C14A C15A C20A 109.3(5) . . ? C20A C15A S1A 109.4(5) . . ? C15A C16A H16A 109.2 . . ? C15A C16A H16B 109.2 . . ? C15A C16A C17A 112.3(5) . . ? H16A C16A H16B 107.9 . . ? C17A C16A H16A 109.2 . . ? C17A C16A H16B 109.2 . . ? N4B C5B C6B 108.4(4) . . ? N4B C5B H5BA 110.0 . . ? N4B C5B H5BB 110.0 . . ? C6B C5B H5BA 110.0 . . ? C6B C5B H5BB 110.0 . . ? H5BA C5B H5BB 108.4 . . ? O5B C13B C6B 108.6(4) . . ? O5B C13B H13C 112(3) . . ? O5B C13B H13D 99(4) . . ? C6B C13B H13C 109(3) . . ? C6B C13B H13D 112(4) . . ? H13C C13B H13D 117(5) . . ? C16B C15B S1B 110.8(4) . . ? C16B C15B C14B 110.9(5) . . ? C16B C15B C20B 111.0(5) . . ? C14B C15B S1B 104.5(4) . . ? C20B C15B S1B 109.4(5) . . ? C20B C15B C14B 109.9(5) . . ? O4A C14A C15A 110.5(4) . . ? O4A C14A H14A 109.5 . . ? O4A C14A H14B 109.5 . . ? C15A C14A H14A 109.5 . . ? C15A C14A H14B 109.5 . . ? H14A C14A H14B 108.1 . . ? C15B C16B H16C 109.0 . . ? C15B C16B H16D 109.0 . . ? C15B C16B C17B 112.8(5) . . ? H16C C16B H16D 107.8 . . ? C17B C16B H16C 109.0 . . ? C17B C16B H16D 109.0 . . ? O4B C14B C15B 110.5(4) . . ? O4B C14B H14C 109.6 . . ? O4B C14B H14D 109.6 . . ? C15B C14B H14C 109.6 . . ? C15B C14B H14D 109.6 . . ? H14C C14B H14D 108.1 . . ? C16A C17A H17A 109.3 . . ? C16A C17A H17B 109.3 . . ? H17A C17A H17B 108.0 . . ? C18A C17A C16A 111.4(7) . . ? C18A C17A H17A 109.3 . . ? C18A C17A H17B 109.3 . . ? C16B C17B H17C 109.5 . . ? C16B C17B H17D 109.5 . . ? H17C C17B H17D 108.1 . . ? C18B C17B C16B 110.9(7) . . ? C18B C17B H17C 109.5 . . ? C18B C17B H17D 109.5 . . ? H19C C19B H19D 108.1 . . ? C18B C19B H19C 109.5 . . ? C18B C19B H19D 109.5 . . ? C18B C19B C20B 110.8(8) . . ? C20B C19B H19C 109.5 . . ? C20B C19B H19D 109.5 . . ? C15A C20A H20A 109.1 . . ? C15A C20A H20B 109.1 . . ? H20A C20A H20B 107.8 . . ? C19A C20A C15A 112.6(6) . . ? C19A C20A H20A 109.1 . . ? C19A C20A H20B 109.1 . . ? C17B C18B C19B 111.6(6) . . ? C17B C18B H18C 109.3 . . ? C17B C18B H18D 109.3 . . ? C19B C18B H18C 109.3 . . ? C19B C18B H18D 109.3 . . ? H18C C18B H18D 108.0 . . ? C15B C20B C19B 111.6(6) . . ? C15B C20B H20C 109.3 . . ? C15B C20B H20D 109.3 . . ? C19B C20B H20C 109.3 . . ? C19B C20B H20D 109.3 . . ? H20C C20B H20D 108.0 . . ? C17A C18A H18A 109.3 . . ? C17A C18A H18B 109.3 . . ? C17A C18A C19A 111.5(6) . . ? H18A C18A H18B 108.0 . . ? C19A C18A H18A 109.3 . . ? C19A C18A H18B 109.3 . . ? C20A C19A H19A 109.4 . . ? C20A C19A H19B 109.4 . . ? C18A C19A C20A 111.3(8) . . ? C18A C19A H19A 109.4 . . ? C18A C19A H19B 109.4 . . ? H19A C19A H19B 108.0 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1A S1A 2.0927(16) . ? P1A S2A 1.9219(16) . ? P1A O4A 1.611(3) . ? P1A N4A 1.636(4) . ? P1B S1B 2.0943(16) . ? P1B S2B 1.9247(16) . ? P1B O4B 1.593(4) . ? P1B N4B 1.632(4) . ? S1B C15B 1.856(5) . ? S1A C15A 1.864(5) . ? O1A C6A 1.450(5) . ? O1A C2A 1.410(5) . ? O2A C8A 1.205(5) . ? O1B C6B 1.437(5) . ? O1B C2B 1.413(5) . ? O5A H5A 0.8200 . ? O5A C13A 1.417(6) . ? O5B H5B 0.8200 . ? O5B C13B 1.411(6) . ? O2B C8B 1.194(5) . ? O4A C14A 1.439(7) . ? O4B C14B 1.431(7) . ? N7A C8A 1.389(5) . ? N7A C12A 1.383(5) . ? N7A C2A 1.463(5) . ? O3A C10A 1.222(6) . ? N9B H9B 0.8600 . ? N9B C8B 1.377(6) . ? N9B C10B 1.378(6) . ? O3B C10B 1.230(6) . ? N4A C3A 1.462(5) . ? N4A C5A 1.469(6) . ? N7B C8B 1.397(5) . ? N7B C12B 1.370(6) . ? N7B C2B 1.460(5) . ? C8A N9A 1.379(5) . ? N4B C3B 1.463(6) . ? N4B C5B 1.475(6) . ? N9A H9A 0.8600 . ? N9A C10A 1.390(6) . ? C6A H6A 0.9800 . ? C6A C13A 1.511(6) . ? C6A C5A 1.502(6) . ? C12A H12A 0.9300 . ? C12A C11A 1.338(6) . ? C10B C11B 1.429(6) . ? C10A C11A 1.427(7) . ? C11A H11A 0.9300 . ? C3B H3BA 0.9700 . ? C3B H3BB 0.9700 . ? C3B C2B 1.518(7) . ? C3A H3AA 0.9700 . ? C3A H3AB 0.9700 . ? C3A C2A 1.506(6) . ? C6B H6B 0.9800 . ? C6B C5B 1.527(7) . ? C6B C13B 1.510(6) . ? C13A H13A 0.9700 . ? C13A H13B 0.9700 . ? C11B H11B 0.9300 . ? C11B C12B 1.337(7) . ? C2A H2A 0.9800 . ? C5A H5AA 0.9700 . ? C5A H5AB 0.9700 . ? C12B H12B 0.9300 . ? C2B H2B 0.9800 . ? C15A C16A 1.510(8) . ? C15A C14A 1.514(8) . ? C15A C20A 1.543(9) . ? C16A H16A 0.9700 . ? C16A H16B 0.9700 . ? C16A C17A 1.523(9) . ? C5B H5BA 0.9700 . ? C5B H5BB 0.9700 . ? C13B H13C 1.01(6) . ? C13B H13D 0.98(7) . ? C15B C16B 1.510(8) . ? C15B C14B 1.540(8) . ? C15B C20B 1.520(9) . ? C14A H14A 0.9700 . ? C14A H14B 0.9700 . ? C16B H16C 0.9700 . ? C16B H16D 0.9700 . ? C16B C17B 1.512(9) . ? C14B H14C 0.9700 . ? C14B H14D 0.9700 . ? C17A H17A 0.9700 . ? C17A H17B 0.9700 . ? C17A C18A 1.498(12) . ? C17B H17C 0.9700 . ? C17B H17D 0.9700 . ? C17B C18B 1.506(13) . ? C19B H19C 0.9700 . ? C19B H19D 0.9700 . ? C19B C18B 1.511(14) . ? C19B C20B 1.536(13) . ? C20A H20A 0.9700 . ? C20A H20B 0.9700 . ? C20A C19A 1.521(13) . ? C18B H18C 0.9700 . ? C18B H18D 0.9700 . ? C20B H20C 0.9700 . ? C20B H20D 0.9700 . ? C18A H18A 0.9700 . ? C18A H18B 0.9700 . ? C18A C19A 1.509(13) . ? C19A H19A 0.9700 . ? C19A H19B 0.9700 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O5A H5A O3A 0.82 2.01 2.796(5) 160.2 1_556 yes O5B H5B O3B 0.82 2.04 2.777(5) 149.4 1_554 yes N9B H9B O5A 0.86 1.97 2.818(5) 167.4 1_455 yes N9A H9A O5B 0.86 2.00 2.838(5) 165.8 . yes 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P1A S1A C15A C16A 109.0(4) . . . . ? P1A S1A C15A C14A -12.7(4) . . . . ? P1A S1A C15A C20A -130.3(4) . . . . ? P1A O4A C14A C15A -54.9(6) . . . . ? P1A N4A C3A C2A 112.8(4) . . . . ? P1A N4A C5A C6A -111.5(4) . . . . ? P1B S1B C15B C16B 104.7(4) . . . . ? P1B S1B C15B C14B -14.8(4) . . . . ? P1B S1B C15B C20B -132.5(4) . . . . ? P1B O4B C14B C15B -53.9(7) . . . . ? P1B N4B C3B C2B 110.9(4) . . . . ? P1B N4B C5B C6B -109.1(4) . . . . ? S1B P1B O4B C14B 35.9(4) . . . . ? S1B P1B N4B C3B -125.9(4) . . . . ? S1B P1B N4B C5B 38.3(4) . . . . ? S1B C15B C16B C17B 68.1(6) . . . . ? S1B C15B C14B O4B 40.3(7) . . . . ? S1B C15B C20B C19B -69.4(8) . . . . ? S1A P1A O4A C14A 38.2(4) . . . . ? S1A P1A N4A C3A -125.6(4) . . . . ? S1A P1A N4A C5A 39.8(4) . . . . ? S1A C15A C16A C17A 67.0(6) . . . . ? S1A C15A C14A O4A 39.6(6) . . . . ? S1A C15A C20A C19A -68.0(7) . . . . ? S2B P1B O4B C14B -86.1(4) . . . . ? S2B P1B N4B C3B 5.6(5) . . . . ? S2B P1B N4B C5B 169.9(3) . . . . ? S2A P1A O4A C14A -83.9(4) . . . . ? S2A P1A N4A C3A 6.5(5) . . . . ? S2A P1A N4A C5A 171.8(3) . . . . ? O1A C6A C13A O5A 64.3(5) . . . . ? O1A C6A C5A N4A -57.5(5) . . . . ? O2A C8A N9A C10A -179.5(5) . . . . ? O1B C6B C5B N4B -59.6(5) . . . . ? O1B C6B C13B O5B 63.8(5) . . . . ? O4A P1A N4A C3A 133.0(4) . . . . ? O4A P1A N4A C5A -61.7(4) . . . . ? O4B P1B N4B C3B 132.2(4) . . . . ? O4B P1B N4B C5B -63.5(4) . . . . ? N7A C8A N9A C10A 0.9(7) . . . . ? N7A C12A C11A C10A 1.7(8) . . . . ? O3A C10A C11A C12A 175.1(5) . . . . ? N9B C10B C11B C12B -6.0(7) . . . . ? O3B C10B C11B C12B 173.7(5) . . . . ? N4A P1A O4A C14A 151.3(4) . . . . ? N4A C3A C2A O1A 56.3(4) . . . . ? N4A C3A C2A N7A 175.4(3) . . . . ? C8A N7A C12A C11A 2.9(7) . . . . ? C8A N7A C2A O1A -141.5(4) . . . . ? C8A N7A C2A C3A 96.5(4) . . . . ? C8A N9A C10A O3A -176.3(5) . . . . ? C8A N9A C10A C11A 3.2(7) . . . . ? N4B P1B O4B C14B 149.1(4) . . . . ? N4B C3B C2B O1B 55.5(5) . . . . ? N4B C3B C2B N7B 173.3(3) . . . . ? N9A C10A C11A C12A -4.5(7) . . . . ? C6A O1A C2A N7A 177.1(3) . . . . ? C6A O1A C2A C3A -60.8(4) . . . . ? C8B N9B C10B O3B -173.0(5) . . . . ? C8B N9B C10B C11B 6.7(7) . . . . ? C8B N7B C12B C11B 2.5(7) . . . . ? C8B N7B C2B O1B -142.7(4) . . . . ? C8B N7B C2B C3B 96.2(4) . . . . ? C12A N7A C8A O2A 176.4(5) . . . . ? C12A N7A C8A N9A -4.1(6) . . . . ? C12A N7A C2A O1A 39.6(5) . . . . ? C12A N7A C2A C3A -82.4(5) . . . . ? C10B N9B C8B O2B 178.3(5) . . . . ? C10B N9B C8B N7B -2.7(7) . . . . ? C10B C11B C12B N7B 1.9(8) . . . . ? C3B N4B C5B C6B 57.1(5) . . . . ? C3A N4A C5A C6A 55.5(5) . . . . ? C6B O1B C2B N7B 178.6(3) . . . . ? C6B O1B C2B C3B -60.4(5) . . . . ? C13A C6A C5A N4A -175.7(4) . . . . ? C2A O1A C6A C13A -176.1(4) . . . . ? C2A O1A C6A C5A 61.1(4) . . . . ? C2A N7A C8A O2A -2.6(7) . . . . ? C2A N7A C8A N9A 177.0(4) . . . . ? C2A N7A C12A C11A -178.2(4) . . . . ? C5A N4A C3A C2A -53.8(5) . . . . ? C5A C6A C13A O5A -175.5(4) . . . . ? C12B N7B C8B O2B 176.9(5) . . . . ? C12B N7B C8B N9B -2.2(6) . . . . ? C12B N7B C2B O1B 35.9(5) . . . . ? C12B N7B C2B C3B -85.2(5) . . . . ? C2B O1B C6B C5B 62.4(4) . . . . ? C2B O1B C6B C13B -175.0(4) . . . . ? C2B N7B C8B O2B -4.5(7) . . . . ? C2B N7B C8B N9B 176.4(4) . . . . ? C2B N7B C12B C11B -176.0(4) . . . . ? C15A C16A C17A C18A 56.3(7) . . . . ? C15A C20A C19A C18A -53.4(10) . . . . ? C16A C15A C14A O4A -79.9(6) . . . . ? C16A C15A C20A C19A 52.3(8) . . . . ? C16A C17A C18A C19A -56.4(10) . . . . ? C5B N4B C3B C2B -54.5(5) . . . . ? C5B C6B C13B O5B -176.1(4) . . . . ? C13B C6B C5B N4B -178.7(4) . . . . ? C15B C16B C17B C18B 55.0(7) . . . . ? C14A C15A C16A C17A -175.7(5) . . . . ? C14A C15A C20A C19A 176.7(7) . . . . ? C16B C15B C14B O4B -79.2(6) . . . . ? C16B C15B C20B C19B 53.2(9) . . . . ? C16B C17B C18B C19B -56.0(9) . . . . ? C14B C15B C16B C17B -176.3(5) . . . . ? C14B C15B C20B C19B 176.3(7) . . . . ? C17A C18A C19A C20A 55.1(11) . . . . ? C20A C15A C16A C17A -53.3(7) . . . . ? C20A C15A C14A O4A 157.2(6) . . . . ? C18B C19B C20B C15B -54.7(10) . . . . ? C20B C15B C16B C17B -53.7(7) . . . . ? C20B C15B C14B O4B 157.7(6) . . . . ? C20B C19B C18B C17B 56.1(10) . . . . ?