#------------------------------------------------------------------------------ #$Date: 2024-12-06 22:32:57 +0200 (Fri, 06 Dec 2024) $ #$Revision: 296659 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160180.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_7160180 loop_ _publ_author_name 'Jastrzębska, Katarzyna' 'Antończyk, Patrycja' 'Dolot, Rafał' _publ_section_title ; P-Stereodefined morpholino dinucleoside 3',5'-phosphorothioates. ; _journal_issue 44 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8737 _journal_page_last 8742 _journal_paper_doi 10.1039/d4ob01437e _journal_volume 22 _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)-(RP)-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 91.566(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.4472(2) _cell_length_b 6.4902(2) _cell_length_c 20.4323(5) _cell_measurement_reflns_used 7794 _cell_measurement_temperature 293.88(10) _cell_measurement_theta_max 76.2630 _cell_measurement_theta_min 4.2650 _cell_volume 987.20(5) _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_environment air _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 0.999 _diffrn_measured_fraction_theta_max 0.961 _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 101.00 139.00 0.50 0.05 -- 107.22 38.00 60.00 76 2 \w 131.00 173.00 0.50 0.05 -- 107.22 57.00 90.00 84 3 \w 142.00 176.00 0.50 0.05 -- 107.22 38.00 60.00 68 4 \w 96.00 121.00 0.50 0.05 -- 107.22 38.00 120.00 50 5 \w 107.00 174.00 0.50 0.05 -- 107.22 19.00 -90.00 134 6 \w 142.00 178.00 0.50 0.05 -- 107.22 57.00-150.00 72 7 \w 104.00 130.00 0.50 0.05 -- 107.22 57.00-150.00 52 8 \w -16.00 25.00 0.50 0.05 -- -47.84 19.00 90.00 82 9 \w -25.00 28.00 0.50 0.05 -- -47.84 19.00 150.00 106 10 \w -60.00 -35.00 0.50 0.05 -- -91.75 57.00-180.00 50 11 \w -65.00 -20.00 0.50 0.05 -- -91.75 57.00 0.00 90 12 \w -54.00 -23.00 0.50 0.05 -- -91.75 57.00 120.00 62 13 \w -73.00 25.00 0.50 0.05 -- -47.84 84.00 162.00 196 14 \w -84.00 -20.00 0.50 0.05 -- -91.75 125.00 150.00 128 15 \w -67.00 -19.00 0.50 0.05 -- -91.75 84.00 162.00 96 16 \w -114.00 -79.00 0.50 0.05 -- -47.84-125.00 120.00 70 17 \w -139.00-113.00 0.50 0.05 -- -91.75 -84.00 42.00 52 18 \w -106.00 -76.00 0.50 0.05 -- -47.84-125.00 -90.00 60 19 \w -107.00 -75.00 0.50 0.05 -- -47.84-125.00-180.00 64 20 \w -160.00-134.00 0.50 0.05 -- -91.75 -19.00-120.00 52 21 \w -112.00 -81.00 0.50 0.05 -- -91.75 -19.00-120.00 62 22 \w -142.00-104.00 0.50 0.05 -- -91.75 -38.00 -60.00 76 23 \w -163.00 -70.00 0.50 0.05 -- -91.75 -77.00 0.00 186 24 \w -145.00-119.00 0.50 0.05 -- -91.75 -77.00 120.00 52 25 \w -109.00 -70.00 0.50 0.05 -- -91.75 -77.00 120.00 78 26 \w -2.00 23.00 0.50 0.05 -- 47.84 -19.00 -30.00 50 27 \w 42.00 68.00 0.50 0.05 -- 107.22 -77.00-150.00 52 28 \w 73.00 98.00 0.50 0.05 -- 107.22 -77.00-150.00 50 29 \w 101.00 178.00 0.50 0.05 -- 107.22 84.00 162.00 154 30 \w 38.00 64.00 0.50 0.05 -- 107.22 -57.00 90.00 52 31 \w 37.00 63.00 0.50 0.05 -- 107.22 -57.00 60.00 52 32 \w 56.00 83.00 0.50 0.05 -- 107.22 -84.00 42.00 54 33 \w 45.00 103.00 0.50 0.05 -- 107.22 -99.00 120.00 116 34 \w 78.00 110.00 0.50 0.05 -- 107.22-125.00 30.00 64 35 \w 80.00 105.00 0.50 0.05 -- 107.22 -99.00 60.00 50 36 \w 38.00 63.00 0.50 0.05 -- 107.22-125.00 30.00 50 37 \w 40.00 69.00 0.50 0.05 -- 107.22-125.00 0.00 58 38 \w 55.00 100.00 0.50 0.05 -- 107.22-125.00-120.00 90 39 \w -9.00 47.00 0.50 0.05 -- 47.84 -84.00 42.00 112 ; _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 0.1784621000 _diffrn_orient_matrix_UB_12 0.0437920000 _diffrn_orient_matrix_UB_13 -0.0337929000 _diffrn_orient_matrix_UB_21 -0.0182748000 _diffrn_orient_matrix_UB_22 -0.2047612000 _diffrn_orient_matrix_UB_23 -0.0377040000 _diffrn_orient_matrix_UB_31 -0.1032889000 _diffrn_orient_matrix_UB_32 0.1118664000 _diffrn_orient_matrix_UB_33 -0.0558632000 _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 0.0390 _diffrn_reflns_av_unetI/netI 0.0384 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.961 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 10844 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.934 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.662 _diffrn_reflns_theta_min 4.329 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.508 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.14779 _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 1.458 _exptl_crystal_description prism _exptl_crystal_F_000 456 _exptl_crystal_recrystallization_method 'Crystallization from the mixture of chloroform : methanol (1:1)' _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.187 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details ; Flack x determined using 1558 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.022(10) _refine_ls_extinction_coef 0.0059(6) _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 1.048 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 3894 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0299 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.0868P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0760 _refine_ls_wR_factor_ref 0.0768 _reflns_Friedel_coverage 0.781 _reflns_Friedel_fraction_full 0.997 _reflns_Friedel_fraction_max 0.902 _reflns_number_gt 3729 _reflns_number_total 3894 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01437e2.cif _cod_data_source_block kjmu_2_01_auto _cod_depositor_comments 'Adding full bibliography for 7160179--7160180.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7160180 _shelx_shelxl_version_number 2018/3 _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 0.721 _shelx_estimated_absorpt_t_min 0.202 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2.a Ternary CH refined with riding coordinates: C6(H6), C2(H2) 2.b Secondary CH2 refined with riding coordinates: C20(H20A,H20B), C14(H14A,H14B), C16(H16A,H16B), C19(H19A,H19B), C13(H13A, H13B), C3(H3A,H3B), C5(H5A,H5B), C17(H17A,H17B), C18(H18A,H18B) 2.c Aromatic/amide H refined with riding coordinates: N9(H9), C11(H11), C12(H12) ; _shelx_res_file ; TITL kjmu_2_01_auto_a.res in P2(1) kjmu_2_01_auto.res created by SHELXL-2018/3 at 06:13:46 on 12-Jul-2024 REM Old TITL kjmu_2_01_auto in P2(1) REM SHELXT solution in P2(1): R1 0.130, Rweak 0.035, Alpha 0.004 REM 0.357 for 4 systematic absences, Orientation as input REM Flack x = 0.140 ( 0.008 ) from 1572 Parsons' quotients REM Formula found by SHELXT: C18 N4 O3 S2 CELL 1.54184 7.4472 6.4902 20.4323 90 91.566 90 ZERR 2 0.0002 0.0002 0.0005 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O P S UNIT 32 48 6 10 2 4 L.S. 4 PLAN 2 SIZE 0.1 0.15 0.67 TEMP 20.73(10) CONF MORE -1 BOND $H fmap 2 acta OMIT 0 0 1 REM REM REM WGHT 0.038700 0.086800 EXTI 0.005856 FVAR 9.50477 P1 5 0.786370 0.662130 0.808734 11.00000 0.02765 0.04200 = 0.03227 0.00213 -0.00362 -0.00396 S1 6 0.895263 0.541700 0.895997 11.00000 0.03095 0.05403 = 0.03182 0.00632 -0.00349 -0.00859 S2 6 0.604934 0.870303 0.819028 11.00000 0.03519 0.04731 = 0.05954 -0.00115 -0.00110 0.00117 O4 4 0.972849 0.737603 0.779455 11.00000 0.03129 0.05739 = 0.03557 0.00870 -0.00313 -0.00915 O1 4 0.748708 0.324710 0.632529 11.00000 0.03736 0.05987 = 0.03488 -0.00238 -0.00622 0.00437 O2 4 0.380522 0.784010 0.619272 11.00000 0.06091 0.04870 = 0.07595 -0.00911 -0.03101 0.00761 O5 4 1.176286 0.131298 0.690460 11.00000 0.04434 0.07371 = 0.07046 -0.01069 -0.01155 0.01678 N7 3 0.473666 0.455125 0.600545 11.00000 0.03869 0.04420 = 0.03626 0.00215 -0.01137 -0.00242 O3 4 0.039453 0.391636 0.481444 11.00000 0.07075 0.06471 = 0.06967 0.01507 -0.04408 -0.01510 N4 3 0.723237 0.470758 0.761258 11.00000 0.03548 0.05037 = 0.03705 -0.00300 -0.01020 0.00085 N9 3 0.215358 0.582648 0.548914 11.00000 0.05014 0.04836 = 0.05200 0.00634 -0.02466 0.00062 AFIX 43 H9 2 0.142922 0.683773 0.541616 11.00000 -1.20000 AFIX 0 C20 1 1.205630 0.733005 0.944387 11.00000 0.03286 0.04020 = 0.04481 -0.00666 -0.00858 -0.00033 AFIX 23 H20A 2 1.317217 0.802439 0.934802 11.00000 -1.20000 H20B 2 1.122856 0.835422 0.960472 11.00000 -1.20000 AFIX 0 C15 1 1.126840 0.638990 0.881297 11.00000 0.02678 0.03914 = 0.03813 0.00001 -0.00335 -0.00443 C8 1 0.357812 0.619533 0.591822 11.00000 0.04364 0.04592 = 0.04432 0.00495 -0.01479 -0.00238 C6 1 0.904807 0.317105 0.675993 11.00000 0.03157 0.04580 = 0.04166 0.00192 -0.00624 -0.00238 AFIX 13 H6 2 0.977940 0.441067 0.670394 11.00000 -1.20000 AFIX 0 C14 1 1.100253 0.806012 0.829289 11.00000 0.03236 0.04787 = 0.04768 0.01039 -0.00842 -0.00889 AFIX 23 H14A 2 1.056668 0.931002 0.849478 11.00000 -1.20000 H14B 2 1.214228 0.836688 0.809582 11.00000 -1.20000 AFIX 0 C16 1 1.249281 0.463199 0.859273 11.00000 0.03445 0.04866 = 0.04799 -0.00947 0.00252 -0.00226 AFIX 23 H16A 2 1.195187 0.397194 0.820975 11.00000 -1.20000 H16B 2 1.363919 0.520062 0.846888 11.00000 -1.20000 AFIX 0 C11 1 0.302321 0.238681 0.528492 11.00000 0.05634 0.04962 = 0.04447 -0.00444 -0.01174 -0.00421 AFIX 43 H11 2 0.287768 0.112605 0.507375 11.00000 -1.20000 AFIX 0 C12 1 0.441171 0.268506 0.570257 11.00000 0.04578 0.04620 = 0.04308 -0.00130 -0.00854 -0.00003 AFIX 43 H12 2 0.518788 0.159227 0.579221 11.00000 -1.20000 AFIX 0 C2 1 0.626104 0.482545 0.647288 11.00000 0.03302 0.04347 = 0.03749 0.00251 -0.00964 -0.00105 AFIX 13 H2 2 0.682168 0.616926 0.640023 11.00000 -1.20000 AFIX 0 C19 1 1.241548 0.573025 0.997600 11.00000 0.04097 0.05481 = 0.04008 0.00047 -0.00911 -0.00644 AFIX 23 H19A 2 1.299347 0.639277 1.035155 11.00000 -1.20000 H19B 2 1.128086 0.516740 1.011477 11.00000 -1.20000 AFIX 0 C13 1 1.008005 0.130234 0.655649 11.00000 0.04121 0.05490 = 0.04855 -0.00518 -0.00346 0.00376 AFIX 23 H13A 2 0.941647 0.006186 0.665787 11.00000 -1.20000 H13B 2 1.026724 0.133481 0.608865 11.00000 -1.20000 AFIX 0 C3 1 0.564383 0.469666 0.717396 11.00000 0.02829 0.05383 = 0.03559 -0.00279 -0.00825 -0.00481 AFIX 23 H3A 2 0.487851 0.586162 0.726973 11.00000 -1.20000 H3B 2 0.496111 0.344208 0.723567 11.00000 -1.20000 AFIX 0 C10 1 0.176438 0.401119 0.516424 11.00000 0.05269 0.05421 = 0.04080 0.01087 -0.01913 -0.01324 C5 1 0.845818 0.301950 0.746036 11.00000 0.04180 0.04258 = 0.04010 0.00044 -0.01129 0.00097 AFIX 23 H5A 2 0.786032 0.171087 0.752608 11.00000 -1.20000 H5B 2 0.950261 0.307559 0.775406 11.00000 -1.20000 AFIX 0 C17 1 1.280686 0.303335 0.912343 11.00000 0.04556 0.03731 = 0.07735 -0.00107 -0.00346 0.00238 AFIX 23 H17A 2 1.362932 0.199224 0.896971 11.00000 -1.20000 H17B 2 1.167910 0.236215 0.921749 11.00000 -1.20000 AFIX 0 C18 1 1.358356 0.400944 0.974734 11.00000 0.04812 0.04357 = 0.06421 0.01190 -0.01482 0.00076 AFIX 23 H18A 2 1.369124 0.297031 1.008736 11.00000 -1.20000 H18B 2 1.477585 0.453661 0.966633 11.00000 -1.20000 AFIX 0 H5 2 1.231216 0.023532 0.677369 11.00000 0.08669 HKLF 4 REM kjmu_2_01_auto_a.res in P2(1) REM wR2 = 0.0768, GooF = S = 1.048, Restrained GooF = 1.048 for all data REM R1 = 0.0299 for 3729 Fo > 4sig(Fo) and 0.0310 for all 3894 data REM 249 parameters refined using 1 restraints END WGHT 0.0387 0.0868 REM Highest difference peak 0.187, deepest hole -0.249, 1-sigma level 0.048 Q1 1 0.9565 0.8828 0.7999 11.00000 0.05 0.19 Q2 1 0.5018 0.6802 0.7199 11.00000 0.05 0.18 ; _shelx_res_checksum 40261 _olex2_exptl_crystal_mounting_method 'Crystal was glued to a support using 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 2.645 _oxdiff_exptl_absorpt_empirical_full_min 0.538 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 P1 P 0.78637(9) 0.66213(11) 0.80873(3) 0.03405(18) Uani 1 1 d . . . . . S1 S 0.89526(9) 0.54170(11) 0.89600(3) 0.03901(19) Uani 1 1 d . . . . . S2 S 0.60493(10) 0.87030(13) 0.81903(4) 0.0474(2) Uani 1 1 d . . . . . O4 O 0.9728(3) 0.7376(4) 0.77945(10) 0.0415(5) Uani 1 1 d . . . . . O1 O 0.7487(3) 0.3247(4) 0.63253(10) 0.0442(5) Uani 1 1 d . . . . . O2 O 0.3805(4) 0.7840(4) 0.61927(14) 0.0625(7) Uani 1 1 d . . . . . O5 O 1.1763(3) 0.1313(5) 0.69046(14) 0.0631(7) Uani 1 1 d . . . . . N7 N 0.4737(3) 0.4551(4) 0.60055(12) 0.0399(6) Uani 1 1 d . . . . . O3 O 0.0395(4) 0.3916(5) 0.48144(13) 0.0692(8) Uani 1 1 d . . . . . N4 N 0.7232(3) 0.4708(4) 0.76126(12) 0.0412(6) Uani 1 1 d . . . . . N9 N 0.2154(4) 0.5826(4) 0.54891(14) 0.0506(7) Uani 1 1 d . . . . . H9 H 0.142922 0.683773 0.541616 0.061 Uiso 1 1 calc R U . . . C20 C 1.2056(4) 0.7330(5) 0.94439(15) 0.0395(7) Uani 1 1 d . . . . . H20A H 1.317217 0.802439 0.934802 0.047 Uiso 1 1 calc R U . . . H20B H 1.122856 0.835422 0.960472 0.047 Uiso 1 1 calc R U . . . C15 C 1.1268(4) 0.6390(5) 0.88130(13) 0.0348(6) Uani 1 1 d . . . . . C8 C 0.3578(5) 0.6195(5) 0.59182(15) 0.0449(7) Uani 1 1 d . . . . . C6 C 0.9048(4) 0.3171(5) 0.67599(15) 0.0398(7) Uani 1 1 d . . . . . H6 H 0.977940 0.441067 0.670394 0.048 Uiso 1 1 calc R U . . . C14 C 1.1003(4) 0.8060(5) 0.82929(15) 0.0428(7) Uani 1 1 d . . . . . H14A H 1.056668 0.931002 0.849478 0.051 Uiso 1 1 calc R U . . . H14B H 1.214228 0.836688 0.809582 0.051 Uiso 1 1 calc R U . . . C16 C 1.2493(4) 0.4632(5) 0.85927(16) 0.0437(7) Uani 1 1 d . . . . . H16A H 1.195187 0.397194 0.820975 0.052 Uiso 1 1 calc R U . . . H16B H 1.363919 0.520062 0.846888 0.052 Uiso 1 1 calc R U . . . C11 C 0.3023(5) 0.2387(5) 0.52849(17) 0.0504(8) Uani 1 1 d . . . . . H11 H 0.287768 0.112605 0.507375 0.060 Uiso 1 1 calc R U . . . C12 C 0.4412(5) 0.2685(5) 0.57026(16) 0.0452(7) Uani 1 1 d . . . . . H12 H 0.518788 0.159227 0.579221 0.054 Uiso 1 1 calc R U . . . C2 C 0.6261(4) 0.4825(5) 0.64729(14) 0.0382(6) Uani 1 1 d . . . . . H2 H 0.682168 0.616926 0.640023 0.046 Uiso 1 1 calc R U . . . C19 C 1.2415(4) 0.5730(5) 0.99760(15) 0.0455(7) Uani 1 1 d . . . . . H19A H 1.299347 0.639277 1.035155 0.055 Uiso 1 1 calc R U . . . H19B H 1.128086 0.516740 1.011477 0.055 Uiso 1 1 calc R U . . . C13 C 1.0080(4) 0.1302(6) 0.65565(16) 0.0483(8) Uani 1 1 d . . . . . H13A H 0.941647 0.006186 0.665787 0.058 Uiso 1 1 calc R U . . . H13B H 1.026724 0.133481 0.608865 0.058 Uiso 1 1 calc R U . . . C3 C 0.5644(4) 0.4697(5) 0.71740(14) 0.0394(7) Uani 1 1 d . . . . . H3A H 0.487851 0.586162 0.726973 0.047 Uiso 1 1 calc R U . . . H3B H 0.496111 0.344208 0.723567 0.047 Uiso 1 1 calc R U . . . C10 C 0.1764(5) 0.4011(6) 0.51642(16) 0.0496(8) Uani 1 1 d . . . . . C5 C 0.8458(4) 0.3020(5) 0.74604(15) 0.0417(7) Uani 1 1 d . . . . . H5A H 0.786032 0.171087 0.752608 0.050 Uiso 1 1 calc R U . . . H5B H 0.950261 0.307559 0.775406 0.050 Uiso 1 1 calc R U . . . C17 C 1.2807(5) 0.3033(5) 0.91234(19) 0.0535(8) Uani 1 1 d . . . . . H17A H 1.362932 0.199224 0.896971 0.064 Uiso 1 1 calc R U . . . H17B H 1.167910 0.236215 0.921749 0.064 Uiso 1 1 calc R U . . . C18 C 1.3584(5) 0.4009(5) 0.97473(19) 0.0523(8) Uani 1 1 d . . . . . H18A H 1.369124 0.297031 1.008736 0.063 Uiso 1 1 calc R U . . . H18B H 1.477585 0.453661 0.966633 0.063 Uiso 1 1 calc R U . . . H5 H 1.231(7) 0.024(9) 0.677(3) 0.087(16) 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 P1 0.0277(3) 0.0420(4) 0.0323(3) 0.0021(3) -0.0036(2) -0.0040(3) S1 0.0310(3) 0.0540(4) 0.0318(3) 0.0063(3) -0.0035(2) -0.0086(3) S2 0.0352(4) 0.0473(4) 0.0595(5) -0.0012(4) -0.0011(3) 0.0012(3) O4 0.0313(10) 0.0574(13) 0.0356(10) 0.0087(9) -0.0031(8) -0.0091(9) O1 0.0374(11) 0.0599(15) 0.0349(11) -0.0024(10) -0.0062(8) 0.0044(10) O2 0.0609(16) 0.0487(14) 0.0759(17) -0.0091(13) -0.0310(13) 0.0076(12) O5 0.0443(14) 0.0737(18) 0.0705(16) -0.0107(15) -0.0116(12) 0.0168(14) N7 0.0387(13) 0.0442(13) 0.0363(13) 0.0021(10) -0.0114(10) -0.0024(11) O3 0.0708(17) 0.0647(16) 0.0697(18) 0.0151(14) -0.0441(14) -0.0151(14) N4 0.0355(13) 0.0504(14) 0.0370(13) -0.0030(11) -0.0102(10) 0.0008(11) N9 0.0501(16) 0.0484(16) 0.0520(16) 0.0063(12) -0.0247(12) 0.0006(12) C20 0.0329(15) 0.0402(16) 0.0448(16) -0.0067(12) -0.0086(12) -0.0003(12) C15 0.0268(13) 0.0391(15) 0.0381(14) 0.0000(12) -0.0033(10) -0.0044(12) C8 0.0436(17) 0.0459(18) 0.0443(16) 0.0050(14) -0.0148(13) -0.0024(14) C6 0.0316(14) 0.0458(17) 0.0417(16) 0.0019(12) -0.0062(12) -0.0024(12) C14 0.0324(15) 0.0479(17) 0.0477(17) 0.0104(14) -0.0084(12) -0.0089(13) C16 0.0344(15) 0.0487(17) 0.0480(18) -0.0095(14) 0.0025(12) -0.0023(14) C11 0.056(2) 0.0496(18) 0.0445(17) -0.0044(14) -0.0117(15) -0.0042(16) C12 0.0458(17) 0.0462(17) 0.0431(17) -0.0013(14) -0.0085(13) 0.0000(15) C2 0.0330(14) 0.0435(16) 0.0375(15) 0.0025(12) -0.0096(11) -0.0011(12) C19 0.0410(16) 0.0548(19) 0.0401(15) 0.0005(14) -0.0091(12) -0.0064(14) C13 0.0412(17) 0.0549(19) 0.0486(17) -0.0052(15) -0.0035(13) 0.0038(15) C3 0.0283(13) 0.0538(17) 0.0356(14) -0.0028(13) -0.0083(11) -0.0048(13) C10 0.0527(18) 0.0542(19) 0.0408(17) 0.0109(14) -0.0191(14) -0.0132(16) C5 0.0418(16) 0.0426(16) 0.0401(16) 0.0004(13) -0.0113(12) 0.0010(13) C17 0.0456(18) 0.0373(17) 0.077(2) -0.0011(16) -0.0035(16) 0.0024(15) C18 0.0481(19) 0.0436(18) 0.064(2) 0.0119(16) -0.0148(16) 0.0008(15) 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 S2 P1 S1 115.22(5) . . ? O4 P1 S1 96.47(8) . . ? O4 P1 S2 116.34(10) . . ? O4 P1 N4 104.38(13) . . ? N4 P1 S1 108.68(10) . . ? N4 P1 S2 113.95(10) . . ? C15 S1 P1 94.29(9) . . ? C14 O4 P1 112.97(18) . . ? C2 O1 C6 114.1(2) . . ? C13 O5 H5 105(4) . . ? C8 N7 C2 117.2(3) . . ? C12 N7 C8 121.3(2) . . ? C12 N7 C2 121.3(3) . . ? C3 N4 P1 125.5(2) . . ? C3 N4 C5 111.4(2) . . ? C5 N4 P1 121.5(2) . . ? C8 N9 H9 116.5 . . ? C8 N9 C10 127.0(3) . . ? C10 N9 H9 116.5 . . ? H20A C20 H20B 107.8 . . ? C15 C20 H20A 109.0 . . ? C15 C20 H20B 109.0 . . ? C19 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C19 C20 C15 112.7(3) . . ? C20 C15 S1 109.5(2) . . ? C20 C15 C16 109.0(2) . . ? C14 C15 S1 104.42(18) . . ? C14 C15 C20 110.1(2) . . ? C14 C15 C16 113.0(3) . . ? C16 C15 S1 110.7(2) . . ? O2 C8 N7 122.7(3) . . ? O2 C8 N9 122.7(3) . . ? N9 C8 N7 114.5(3) . . ? O1 C6 H6 109.9 . . ? O1 C6 C13 105.5(2) . . ? O1 C6 C5 109.5(2) . . ? C13 C6 H6 109.9 . . ? C13 C6 C5 112.0(3) . . ? C5 C6 H6 109.9 . . ? O4 C14 C15 110.1(2) . . ? O4 C14 H14A 109.6 . . ? O4 C14 H14B 109.6 . . ? C15 C14 H14A 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.2 . . ? C15 C16 H16A 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C17 C16 C15 112.4(3) . . ? C17 C16 H16A 109.1 . . ? C17 C16 H16B 109.1 . . ? C12 C11 H11 120.1 . . ? C12 C11 C10 119.7(3) . . ? C10 C11 H11 120.1 . . ? N7 C12 H12 118.8 . . ? C11 C12 N7 122.5(3) . . ? C11 C12 H12 118.8 . . ? O1 C2 N7 105.4(2) . . ? O1 C2 H2 109.5 . . ? O1 C2 C3 112.1(2) . . ? N7 C2 H2 109.5 . . ? N7 C2 C3 110.9(2) . . ? C3 C2 H2 109.5 . . ? C20 C19 H19A 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C18 C19 C20 112.2(3) . . ? C18 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? O5 C13 C6 107.9(3) . . ? O5 C13 H13A 110.1 . . ? O5 C13 H13B 110.1 . . ? C6 C13 H13A 110.1 . . ? C6 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? N4 C3 C2 108.5(2) . . ? N4 C3 H3A 110.0 . . ? N4 C3 H3B 110.0 . . ? C2 C3 H3A 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? O3 C10 N9 118.8(3) . . ? O3 C10 C11 126.4(4) . . ? N9 C10 C11 114.8(3) . . ? N4 C5 C6 110.6(2) . . ? N4 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C16 C17 H17A 109.4 . . ? C16 C17 H17B 109.4 . . ? C16 C17 C18 111.2(3) . . ? H17A C17 H17B 108.0 . . ? C18 C17 H17A 109.4 . . ? C18 C17 H17B 109.4 . . ? C19 C18 C17 111.1(3) . . ? C19 C18 H18A 109.4 . . ? C19 C18 H18B 109.4 . . ? C17 C18 H18A 109.4 . . ? C17 C18 H18B 109.4 . . ? H18A C18 H18B 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 P1 S1 2.0901(9) . ? P1 S2 1.9264(11) . ? P1 O4 1.604(2) . ? P1 N4 1.637(3) . ? S1 C15 1.869(3) . ? O4 C14 1.443(4) . ? O1 C6 1.444(3) . ? O1 C2 1.410(4) . ? O2 C8 1.216(4) . ? O5 C13 1.424(4) . ? O5 H5 0.86(6) . ? N7 C8 1.381(4) . ? N7 C12 1.379(4) . ? N7 C2 1.474(3) . ? O3 C10 1.231(4) . ? N4 C3 1.465(3) . ? N4 C5 1.465(4) . ? N9 H9 0.8600 . ? N9 C8 1.379(4) . ? N9 C10 1.379(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 C15 1.529(4) . ? C20 C19 1.522(4) . ? C15 C14 1.527(4) . ? C15 C16 1.536(4) . ? C6 H6 0.9800 . ? C6 C13 1.501(5) . ? C6 C5 1.512(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.514(5) . ? C11 H11 0.9300 . ? C11 C12 1.337(4) . ? C11 C10 1.428(5) . ? C12 H12 0.9300 . ? C2 H2 0.9800 . ? C2 C3 1.519(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 C18 1.498(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C18 1.523(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? 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 P1 S1 C15 C20 136.00(19) . . . . ? P1 S1 C15 C14 18.2(2) . . . . ? P1 S1 C15 C16 -103.71(19) . . . . ? P1 O4 C14 C15 53.6(3) . . . . ? P1 N4 C3 C2 108.4(3) . . . . ? P1 N4 C5 C6 -107.6(3) . . . . ? S1 P1 O4 C14 -33.5(2) . . . . ? S1 P1 N4 C3 143.8(2) . . . . ? S1 P1 N4 C5 -52.2(3) . . . . ? S1 C15 C14 O4 -42.8(3) . . . . ? S1 C15 C16 C17 -65.7(3) . . . . ? S2 P1 O4 C14 88.9(2) . . . . ? S2 P1 N4 C3 13.8(3) . . . . ? S2 P1 N4 C5 177.9(2) . . . . ? O4 P1 N4 C3 -114.1(3) . . . . ? O4 P1 N4 C5 49.9(3) . . . . ? O1 C6 C13 O5 171.7(3) . . . . ? O1 C6 C5 N4 -54.8(3) . . . . ? O1 C2 C3 N4 55.2(3) . . . . ? N7 C2 C3 N4 172.7(3) . . . . ? N4 P1 O4 C14 -144.7(2) . . . . ? C20 C15 C14 O4 -160.2(2) . . . . ? C20 C15 C16 C17 54.9(3) . . . . ? C20 C19 C18 C17 -54.1(4) . . . . ? C15 C20 C19 C18 54.7(4) . . . . ? C15 C16 C17 C18 -56.4(4) . . . . ? C8 N7 C12 C11 3.5(5) . . . . ? C8 N7 C2 O1 -162.6(3) . . . . ? C8 N7 C2 C3 75.8(3) . . . . ? C8 N9 C10 O3 177.4(4) . . . . ? C8 N9 C10 C11 -1.6(5) . . . . ? C6 O1 C2 N7 -176.5(2) . . . . ? C6 O1 C2 C3 -55.7(3) . . . . ? C14 C15 C16 C17 177.6(2) . . . . ? C16 C15 C14 O4 77.7(3) . . . . ? C16 C17 C18 C19 55.1(4) . . . . ? C12 N7 C8 O2 178.0(3) . . . . ? C12 N7 C8 N9 -2.7(5) . . . . ? C12 N7 C2 O1 21.7(4) . . . . ? C12 N7 C2 C3 -99.8(3) . . . . ? C12 C11 C10 O3 -176.8(4) . . . . ? C12 C11 C10 N9 2.0(5) . . . . ? C2 O1 C6 C13 175.3(3) . . . . ? C2 O1 C6 C5 54.6(3) . . . . ? C2 N7 C8 O2 2.3(5) . . . . ? C2 N7 C8 N9 -178.3(3) . . . . ? C2 N7 C12 C11 178.9(3) . . . . ? C19 C20 C15 S1 67.7(3) . . . . ? C19 C20 C15 C14 -178.0(3) . . . . ? C19 C20 C15 C16 -53.6(3) . . . . ? C13 C6 C5 N4 -171.5(2) . . . . ? C3 N4 C5 C6 58.5(3) . . . . ? C10 N9 C8 O2 -178.8(4) . . . . ? C10 N9 C8 N7 1.9(5) . . . . ? C10 C11 C12 N7 -3.0(5) . . . . ? C5 N4 C3 C2 -57.0(3) . . . . ? C5 C6 C13 O5 -69.2(4) . . . . ?