#------------------------------------------------------------------------------ #$Date: 2019-11-08 02:46:23 +0200 (Fri, 08 Nov 2019) $ #$Revision: 224858 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/83/7058315.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_7058315 loop_ _publ_author_name 'T\(anase, Constantin I.' 'Cocu, Florea' 'Dr\(aghici, Constantin' 'Hanganu, Anamaria' 'Pintilie, Lucia' 'Maganu, Maria' 'Munteanu, Cristian V. A.' 'Shova, Sergiu' _publ_section_title ; Secondary compounds in the catalytic hydrogenation of enone and allylic alcohol prostaglandin intermediates: isolation, characterization, and X-ray crystallography ; _journal_issue 20 _journal_name_full 'New Journal of Chemistry' _journal_page_first 7582 _journal_paper_doi 10.1039/C9NJ01186B _journal_volume 43 _journal_year 2019 _chemical_absolute_configuration unk _chemical_formula_moiety '4(C10 H13 N3 O2), 4(H2 O)' _chemical_formula_sum 'C40 H60 N12 O12' _chemical_formula_weight 901.00 _space_group_crystal_system triclinic _space_group_IT_number 1 _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 geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_block_doi 10.5517/ccdc.csd.cc1pdf0j _audit_creation_date 2017-07-09 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2017-07-09 deposited with the CCDC. 2019-04-18 downloaded from the CCDC. ; _cell_angle_alpha 110.945(4) _cell_angle_beta 98.955(3) _cell_angle_gamma 92.334(3) _cell_formula_units_Z 1 _cell_length_a 6.6116(2) _cell_length_b 12.1182(5) _cell_length_c 15.0179(7) _cell_measurement_reflns_used 5949 _cell_measurement_temperature 200.00(10) _cell_measurement_theta_max 29.0250 _cell_measurement_theta_min 1.7990 _cell_volume 1103.97(8) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 200.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0797 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -19.00 21.00 1.00 5.00 -- -15.76 -99.00 30.00 40 2 \w -24.00 17.00 1.00 5.00 -- -15.76 -99.00 -90.00 41 3 \w -42.00 84.00 1.00 5.00 -- 17.94 0.00-150.00 126 4 \w 0.00 69.00 1.00 5.00 -- 17.94 38.00 -90.00 69 5 \w 4.00 38.00 1.00 5.00 -- 17.94 -77.00 150.00 34 6 \w -88.00 -39.00 1.00 5.00 -- -15.76-178.00 -90.00 49 7 \w -64.00 -14.00 1.00 5.00 -- -15.44 116.00-122.00 50 8 \w -25.00 22.00 1.00 5.00 -- -15.44 -99.00 120.00 47 9 \w -23.00 3.00 1.00 5.00 -- -15.44 -99.00 0.00 26 10 \w 53.00 79.00 1.00 5.00 -- 17.79 57.00 -30.00 26 11 \w 3.00 37.00 1.00 5.00 -- 17.79 57.00 -30.00 34 12 \w 30.00 57.00 1.00 5.00 -- 17.79 -99.00 60.00 27 13 \w 10.00 57.00 1.00 5.00 -- 17.79 -99.00-120.00 47 14 \w -30.00 20.00 1.00 5.00 -- 17.79 -57.00 60.00 50 15 \w -51.00 -1.00 1.00 5.00 -- 17.79 0.00 90.00 50 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0327156000 _diffrn_orient_matrix_UB_12 -0.0372574000 _diffrn_orient_matrix_UB_13 -0.0493816000 _diffrn_orient_matrix_UB_21 -0.0212669000 _diffrn_orient_matrix_UB_22 0.0505224000 _diffrn_orient_matrix_UB_23 -0.0118333000 _diffrn_orient_matrix_UB_31 0.1020013000 _diffrn_orient_matrix_UB_32 0.0056338000 _diffrn_orient_matrix_UB_33 -0.0082582000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_unetI/netI 0.0480 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 16607 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 1.48 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92490 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.180 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.037 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 577 _refine_ls_number_reflns 7727 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0455 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.0368P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.0978 _reflns_number_gt 6834 _reflns_number_total 7727 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL shi_3363_cota_a.res in P1 REM Old TITL shI_3363_CoTa in P-1 #2 REM SHELXT solution in P1 REM R1 0.147, Rweak 0.029, Alpha 0.000, Orientation as input REM Flack x = -0.192 ( 0.494 ) from Parsons' quotients REM Formula found by SHELXT: C8D N13 O9 CELL 0.71073 6.611644 12.118238 15.017892 110.9453 98.9546 92.3335 ZERR 1 0.000204 0.000469 0.000684 0.0039 0.0031 0.0028 LATT -1 SFAC C H N O UNIT 40 60 12 12 EQIV $1 1+X,-1+Y,+Z EQIV $2 -1+X,1+Y,+Z EQIV $3 -1+X,+Y,+Z EQIV $4 1+X,+Y,+Z L.S. 11 PLAN 5 HTAB O2A N1A_$1 HTAB N2A O4W HTAB O2C N1C_$2 HTAB N2C O1W HTAB O2B N1B_$1 HTAB N2B O3W_$3 HTAB O2D N1D_$1 HTAB N2D O2W HTAB O1W O2D_$3 HTAB O1W O1C_$4 HTAB O1W N3C_$4 HTAB O3W O1A HTAB O3W O1B HTAB O3W N3B HTAB O2W O1D_$3 HTAB O2W O2C_$4 HTAB O4W O1A_$3 HTAB O4W O2B_$3 htab BOND $H CONF fmap 2 acta 52 SHEL 99 0.84 OMIT 0 1 0 OMIT 0 0 -2 OMIT 0 0 2 REM REM REM WGHT 0.045300 0.036800 FVAR 0.89241 O1A 4 1.155872 1.220600 1.373770 11.00000 0.01614 0.02420 = 0.06796 0.01757 0.01101 0.00579 O2A 4 1.505741 0.744379 1.410047 11.00000 0.02587 0.03068 = 0.08426 0.02582 0.00973 0.01031 AFIX 3 H2A 2 1.554391 0.681379 1.403547 11.00000 -1.50000 AFIX 0 N1A 3 0.646828 1.515679 1.387806 11.00000 0.02600 0.02335 = 0.03182 0.00926 0.00099 0.00670 N2A 3 0.863587 1.110317 1.365724 11.00000 0.01341 0.01785 = 0.03094 0.01010 0.00746 0.00631 AFIX 43 H2AA 2 0.732122 1.105480 1.361713 11.00000 -1.20000 AFIX 0 N3A 3 0.972800 1.014681 1.366891 11.00000 0.02074 0.01917 = 0.02915 0.01150 0.00580 0.00686 C1A 1 0.562501 1.427193 1.406723 11.00000 0.01752 0.02248 = 0.03405 0.00813 0.00439 0.00573 AFIX 43 H1A 2 0.434289 1.434395 1.425180 11.00000 -1.20000 AFIX 0 C2A 1 0.654795 1.324377 1.400537 11.00000 0.02037 0.02383 = 0.03056 0.01277 0.00578 0.00141 AFIX 43 H2AB 2 0.588244 1.264132 1.413391 11.00000 -1.20000 AFIX 0 C3A 1 0.847324 1.312994 1.374946 11.00000 0.02080 0.01516 = 0.01557 0.00160 0.00072 0.00097 C4A 1 0.936950 1.405099 1.355229 11.00000 0.02099 0.02403 = 0.03041 0.00906 0.00818 0.00589 AFIX 43 H4A 2 1.065833 1.400713 1.337424 11.00000 -1.20000 AFIX 0 C5A 1 0.833108 1.502921 1.362305 11.00000 0.03010 0.02076 = 0.03512 0.01401 0.00409 0.00032 AFIX 43 H5A 2 0.895233 1.563826 1.348672 11.00000 -1.20000 AFIX 0 C6A 1 0.968427 1.209507 1.370994 11.00000 0.02046 0.01954 = 0.02538 0.00701 0.00856 0.00433 C7A 1 0.864128 0.921463 1.359244 11.00000 0.02071 0.02282 = 0.03070 0.01083 0.00684 0.00672 AFIX 43 H7A 2 0.721676 0.920251 1.351957 11.00000 -1.20000 AFIX 0 C8A 1 0.963254 0.814802 1.361881 11.00000 0.02806 0.01875 = 0.02865 0.01015 0.00677 0.00260 AFIX 23 H8AA 2 0.910189 0.748990 1.301597 11.00000 -1.20000 H8AB 2 0.923199 0.794484 1.414018 11.00000 -1.20000 AFIX 0 C9A 1 1.198058 0.827694 1.376208 11.00000 0.02947 0.02463 = 0.03420 0.01348 0.00928 0.00686 AFIX 23 H9AA 2 1.239444 0.829523 1.317514 11.00000 -1.20000 H9AB 2 1.251724 0.902500 1.428372 11.00000 -1.20000 AFIX 0 C10A 1 1.290041 0.727073 1.400067 11.00000 0.02766 0.02680 = 0.04002 0.01880 0.00801 0.00851 AFIX 23 H10A 2 1.253789 0.726024 1.459932 11.00000 -1.20000 H10B 2 1.236714 0.651624 1.348638 11.00000 -1.20000 AFIX 0 O1C 4 -0.038046 0.523537 0.894068 11.00000 0.02388 0.03826 = 0.06660 0.03267 0.01926 0.01303 O2C 4 -0.381692 1.004560 0.867688 11.00000 0.02276 0.02619 = 0.05044 0.01492 0.00646 0.01036 AFIX 3 H2C 2 -0.429072 1.068091 0.875118 11.00000 -1.50000 AFIX 0 N1C 3 0.451701 0.219729 0.884362 11.00000 0.02838 0.02066 = 0.03842 0.01167 0.00693 0.00798 N2C 3 0.244353 0.615023 0.871768 11.00000 0.01523 0.02178 = 0.03272 0.01218 0.00650 0.00944 AFIX 43 H2CA 2 0.370659 0.613209 0.864261 11.00000 -1.20000 AFIX 0 N3C 3 0.137027 0.712008 0.872170 11.00000 0.02422 0.02158 = 0.02562 0.01143 0.00594 0.01059 C1C 1 0.282544 0.246846 0.922663 11.00000 0.02937 0.02371 = 0.04716 0.01832 0.00727 0.00411 AFIX 43 H1C 2 0.230088 0.197531 0.950782 11.00000 -1.20000 AFIX 0 C2C 1 0.182592 0.343451 0.922620 11.00000 0.02268 0.02348 = 0.03435 0.01037 0.00688 0.00376 AFIX 43 H2CB 2 0.063607 0.357558 0.949022 11.00000 -1.20000 AFIX 0 C3C 1 0.258985 0.420476 0.883100 11.00000 0.01960 0.02357 = 0.02441 0.00841 0.00314 0.00517 C4C 1 0.435648 0.392791 0.843528 11.00000 0.02945 0.02888 = 0.03494 0.01565 0.01203 0.00935 AFIX 43 H4C 2 0.492934 0.440904 0.815635 11.00000 -1.20000 AFIX 0 C5C 1 0.524393 0.292751 0.846374 11.00000 0.02972 0.03268 = 0.04620 0.01922 0.01853 0.01789 AFIX 43 H5C 2 0.642789 0.275538 0.819925 11.00000 -1.20000 AFIX 0 C6C 1 0.141412 0.524095 0.883673 11.00000 0.02479 0.02572 = 0.02412 0.01079 0.00492 0.00951 C7C 1 0.245449 0.800299 0.870590 11.00000 0.01552 0.02296 = 0.03485 0.01217 0.00517 0.00561 AFIX 43 H7C 2 0.385086 0.796216 0.869047 11.00000 -1.20000 AFIX 0 C8C 1 0.151060 0.910298 0.871184 11.00000 0.02156 0.02416 = 0.03481 0.01338 0.00441 0.00432 AFIX 23 H8CA 2 0.183295 0.928600 0.816821 11.00000 -1.20000 H8CB 2 0.214657 0.975540 0.930049 11.00000 -1.20000 AFIX 0 C9C 1 -0.080447 0.903900 0.865416 11.00000 0.02158 0.01771 = 0.02185 0.00682 0.00516 0.00448 AFIX 23 H9CA 2 -0.146455 0.846106 0.802845 11.00000 -1.20000 H9CB 2 -0.115680 0.876765 0.915044 11.00000 -1.20000 AFIX 0 C10C 1 -0.162112 1.021887 0.878639 11.00000 0.02041 0.02315 = 0.03090 0.01033 0.00642 0.00384 AFIX 23 H10C 2 -0.103906 1.079525 0.942545 11.00000 -1.20000 H10D 2 -0.125054 1.051299 0.830540 11.00000 -1.20000 AFIX 0 O1B 4 0.943294 1.358183 1.107694 11.00000 0.02428 0.03825 = 0.06857 0.03450 0.02088 0.01456 O2B 4 1.274011 0.870374 1.132695 11.00000 0.01811 0.01834 = 0.04869 0.01184 0.00592 0.00865 AFIX 3 H2B 2 1.321821 0.807094 1.126025 11.00000 -1.50000 AFIX 0 N1B 3 0.440883 1.656486 1.111813 11.00000 0.03328 0.02138 = 0.03366 0.00967 0.00241 0.00949 N2B 3 0.660692 1.264715 1.127190 11.00000 0.01659 0.02624 = 0.03270 0.01680 0.00756 0.01030 AFIX 43 H2BA 2 0.533460 1.266164 1.133169 11.00000 -1.20000 AFIX 0 N3B 3 0.764134 1.166986 1.126782 11.00000 0.01896 0.02207 = 0.02572 0.01010 0.00559 0.00935 C1B 1 0.369852 1.581722 1.150242 11.00000 0.03100 0.03405 = 0.03376 0.01304 0.01103 0.01330 AFIX 43 H1B 2 0.250279 1.597225 1.175972 11.00000 -1.20000 AFIX 0 C2B 1 0.463313 1.482870 1.154036 11.00000 0.03009 0.02711 = 0.03386 0.01752 0.01010 0.01193 AFIX 43 H2BB 2 0.406922 1.433177 1.180814 11.00000 -1.20000 AFIX 0 C3B 1 0.643031 1.459831 1.116922 11.00000 0.02347 0.01703 = 0.02579 0.00775 0.00230 0.00449 C4B 1 0.719495 1.536683 1.078399 11.00000 0.01856 0.02476 = 0.03703 0.01288 0.00458 0.00521 AFIX 43 H4B 2 0.841100 1.524466 1.054024 11.00000 -1.20000 AFIX 0 C5B 1 0.614875 1.631410 1.076259 11.00000 0.03105 0.01906 = 0.04152 0.01403 0.00471 0.00058 AFIX 43 H5B 2 0.667473 1.681187 1.048574 11.00000 -1.20000 AFIX 0 C6B 1 0.762444 1.355848 1.118153 11.00000 0.02207 0.02616 = 0.03152 0.01581 0.00659 0.00820 C7B 1 0.650733 1.074132 1.115075 11.00000 0.01537 0.02864 = 0.02838 0.01360 0.00484 0.00699 AFIX 43 H7B 2 0.509045 1.076508 1.109489 11.00000 -1.20000 AFIX 0 C8B 1 0.738588 0.961806 1.110075 11.00000 0.02477 0.02056 = 0.03062 0.00968 0.00618 0.00562 AFIX 23 H8BA 2 0.683710 0.901084 1.047129 11.00000 -1.20000 H8BB 2 0.693549 0.936368 1.158804 11.00000 -1.20000 AFIX 0 C9B 1 0.974219 0.970702 1.125524 11.00000 0.02345 0.01918 = 0.02322 0.00956 0.00362 0.00157 AFIX 23 H9BA 2 1.020746 1.000232 1.079254 11.00000 -1.20000 H9BB 2 1.030146 1.027381 1.190122 11.00000 -1.20000 AFIX 0 C10B 1 1.056240 0.851798 1.113697 11.00000 0.01722 0.01870 = 0.03097 0.01103 0.00434 0.00413 AFIX 23 H10E 2 1.008790 0.820331 1.158691 11.00000 -1.20000 H10F 2 1.007442 0.795257 1.048274 11.00000 -1.20000 AFIX 0 O1D 4 1.170747 0.978541 0.616507 11.00000 0.01780 0.03364 = 0.06493 0.02490 0.01010 0.00847 O2D 4 1.505721 0.480042 0.631224 11.00000 0.02348 0.02745 = 0.04841 0.01581 0.00916 0.01242 AFIX 3 H2D 2 1.572381 0.419772 0.619714 11.00000 -1.50000 AFIX 0 N1D 3 0.643031 1.259204 0.611423 11.00000 0.02686 0.02773 = 0.04629 0.01879 0.01008 0.01283 N2D 3 0.880577 0.868881 0.612758 11.00000 0.01735 0.01968 = 0.03193 0.01033 0.00617 0.00773 AFIX 43 H2DA 2 0.749913 0.865521 0.611436 11.00000 -1.20000 AFIX 0 N3D 3 0.988511 0.772355 0.613003 11.00000 0.02036 0.01990 = 0.02640 0.00888 0.00227 0.00713 C1D 1 0.552234 1.148605 0.572909 11.00000 0.02411 0.03246 = 0.04426 0.01885 0.00440 0.00935 AFIX 43 H1D 2 0.413900 1.136552 0.544226 11.00000 -1.20000 AFIX 0 C2D 1 0.651092 1.050533 0.572955 11.00000 0.02399 0.02353 = 0.04175 0.01244 0.00086 0.00053 AFIX 43 H2DB 2 0.579921 0.974940 0.546287 11.00000 -1.20000 AFIX 0 C3D 1 0.858487 1.066742 0.613488 11.00000 0.02352 0.01832 = 0.02562 0.00947 0.00880 0.00538 C4D 1 0.956480 1.181056 0.652447 11.00000 0.02277 0.02587 = 0.04811 0.01681 0.00414 0.00484 AFIX 43 H4D 2 1.096013 1.195034 0.679278 11.00000 -1.20000 AFIX 0 C5D 1 0.844008 1.274374 0.650951 11.00000 0.03641 0.02112 = 0.04864 0.01241 0.00859 0.00153 AFIX 43 H5D 2 0.910465 1.351155 0.678561 11.00000 -1.20000 AFIX 0 C6D 1 0.985255 0.966781 0.614630 11.00000 0.01982 0.01838 = 0.02688 0.00713 0.00415 0.00245 C7D 1 0.880715 0.684829 0.616713 11.00000 0.01879 0.02178 = 0.02423 0.00464 0.00130 0.00680 AFIX 43 H7D 2 0.740307 0.687697 0.616528 11.00000 -1.20000 AFIX 0 C8D 1 0.978318 0.578899 0.621303 11.00000 0.02229 0.01822 = 0.02804 0.00602 0.00526 0.00247 AFIX 23 H8DA 2 0.905126 0.509473 0.568526 11.00000 -1.20000 H8DB 2 0.961245 0.570056 0.681478 11.00000 -1.20000 AFIX 0 C9D 1 1.205637 0.580302 0.615602 11.00000 0.02237 0.02393 = 0.03182 0.01276 0.00474 0.00254 AFIX 23 H9DA 2 1.225675 0.590293 0.556195 11.00000 -1.20000 H9DB 2 1.282039 0.647156 0.669774 11.00000 -1.20000 AFIX 0 C10D 1 1.286837 0.466942 0.617772 11.00000 0.02490 0.02359 = 0.03194 0.01081 0.00471 0.00951 AFIX 23 H10G 2 1.244134 0.448637 0.670312 11.00000 -1.20000 H10H 2 1.231248 0.401917 0.557343 11.00000 -1.20000 AFIX 0 O1W 4 0.638423 0.640426 0.825246 11.00000 0.01813 0.03340 = 0.06131 0.01537 0.00879 0.00800 AFIX 3 H1WA 2 0.601173 0.585586 0.769646 11.00000 -1.50000 H1WB 2 0.760273 0.639556 0.853026 11.00000 -1.50000 AFIX 0 O3W 4 1.259002 1.240729 1.172227 11.00000 0.02425 0.05032 = 0.07810 0.03988 0.01560 0.01091 AFIX 3 H3WA 2 1.239322 1.228479 1.222667 11.00000 -1.50000 H3WB 2 1.150542 1.262729 1.147846 11.00000 -1.50000 AFIX 0 O2W 4 0.497636 0.856083 0.671061 11.00000 0.02229 0.04221 = 0.04002 0.01411 0.00379 0.01232 AFIX 3 H2WA 2 0.395036 0.878653 0.642900 11.00000 -1.50000 H2WB 2 0.525026 0.900663 0.730760 11.00000 -1.50000 AFIX 0 O4W 4 0.435830 1.052259 1.306957 11.00000 0.01615 0.04002 = 0.05302 -0.00383 0.00572 0.00120 AFIX 3 H4WA 2 0.348340 1.096929 1.332607 11.00000 -1.50000 H4WB 2 0.349850 1.005809 1.257507 11.00000 -1.50000 HKLF 4 REM shi_3363_cota_a.res in P1 REM R1 = 0.0455 for 6834 Fo > 4sig(Fo) and 0.0533 for all 7727 data REM 577 parameters refined using 3 restraints END WGHT 0.0453 0.0368 REM Highest difference peak 0.180, deepest hole -0.194, 1-sigma level 0.037 Q1 1 0.8756 1.3327 1.3427 11.00000 0.05 0.15 Q2 1 0.5789 0.5519 0.8268 11.00000 0.05 0.15 Q3 1 0.2090 0.4802 0.8949 11.00000 0.05 0.15 Q4 1 -0.0098 0.7196 0.8632 11.00000 0.05 0.14 Q5 1 0.8962 1.1632 1.1477 11.00000 0.05 0.14 REM The information below was added by Olex2. REM REM R1 = 0.0455 for 6834 Fo > 4sig(Fo) and 0.0533 for all 19655 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.18, deepest hole -0.19 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0533 REM R1_gt = 0.0455 REM wR_ref = 0.0978 REM GOOF = 1.029 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 19655 REM Reflections_gt = 6834 REM Parameters = n/a REM Hole = -0.19 REM Peak = 0.18 REM Flack = 0.2(8) ; _cod_data_source_file c9nj01186b2.cif _cod_data_source_block shi_3363_cota _cod_depositor_comments 'Adding full bibliography for 7058315--7058316.cif.' _cod_original_cell_volume 1103.98(7) _cod_database_code 7058315 _chemical_oxdiff_formula 'C10 H10 N3 O1' _chemical_oxdiff_usercomment TVC_3416 _reflns_odcompleteness_completeness 99.98 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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, All O(H,H) groups 2.a Riding coordinates: O2A(H2A), O2C(H2C), O2B(H2B), O2D(H2D), O1W(H1WA,H1WB), O3W(H3WA,H3WB), O2W(H2WA,H2WB), O4W(H4WA,H4WB) 2.b Secondary CH2 refined with riding coordinates: C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10A,H10B), C8C(H8CA,H8CB), C9C(H9CA, H9CB), C10C(H10C,H10D), C8B(H8BA,H8BB), C9B(H9BA,H9BB), C10B(H10E,H10F), C8D(H8DA,H8DB), C9D(H9DA,H9DB), C10D(H10G,H10H) 2.c Aromatic/amide H refined with riding coordinates: N2A(H2AA), C1A(H1A), C2A(H2AB), C4A(H4A), C5A(H5A), C7A(H7A), N2C(H2CA), C1C(H1C), C2C(H2CB), C4C(H4C), C5C(H5C), C7C(H7C), N2B(H2BA), C1B(H1B), C2B(H2BB), C4B(H4B), C5B(H5B), C7B(H7B), N2D(H2DA), C1D(H1D), C2D(H2DB), C4D(H4D), C5D(H5D), C7D(H7D) ; _olex2_date_sample_data_collection 2016-12-13 _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 1.136 _oxdiff_exptl_absorpt_empirical_full_min 0.807 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 '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_calc_flag _atom_site_refinement_flags_posn O1A O 1.1559(2) 1.22060(16) 1.37377(15) 0.0354(5) Uani 1 d . O2A O 1.5057(3) 0.74438(17) 1.41005(16) 0.0455(6) Uani 1 d . H2A H 1.5544 0.6814 1.4035 0.068 Uiso 1 d R N1A N 0.6468(3) 1.51568(19) 1.38781(16) 0.0277(5) Uani 1 d . N2A N 0.8636(3) 1.11032(18) 1.36572(15) 0.0199(5) Uani 1 d . H2AA H 0.7321 1.1055 1.3617 0.024 Uiso 1 calc R N3A N 0.9728(3) 1.01468(19) 1.36689(15) 0.0220(5) Uani 1 d . C1A C 0.5625(4) 1.4272(2) 1.40672(19) 0.0252(6) Uani 1 d . H1A H 0.4343 1.4344 1.4252 0.030 Uiso 1 calc R C2A C 0.6548(4) 1.3244(2) 1.40054(19) 0.0240(6) Uani 1 d . H2AB H 0.5882 1.2641 1.4134 0.029 Uiso 1 calc R C3A C 0.8473(4) 1.3130(2) 1.37495(17) 0.0186(5) Uani 1 d . C4A C 0.9370(4) 1.4051(2) 1.35523(18) 0.0249(6) Uani 1 d . H4A H 1.0658 1.4007 1.3374 0.030 Uiso 1 calc R C5A C 0.8331(4) 1.5029(2) 1.36231(19) 0.0279(6) Uani 1 d . H5A H 0.8952 1.5638 1.3487 0.033 Uiso 1 calc R C6A C 0.9684(4) 1.2095(2) 1.37099(18) 0.0216(6) Uani 1 d . C7A C 0.8641(4) 0.9215(2) 1.35924(19) 0.0241(6) Uani 1 d . H7A H 0.7217 0.9203 1.3520 0.029 Uiso 1 calc R C8A C 0.9633(4) 0.8148(2) 1.3619(2) 0.0246(6) Uani 1 d . H8AA H 0.9102 0.7490 1.3016 0.029 Uiso 1 calc R H8AB H 0.9232 0.7945 1.4140 0.029 Uiso 1 calc R C9A C 1.1981(4) 0.8277(2) 1.3762(2) 0.0282(6) Uani 1 d . H9AA H 1.2394 0.8295 1.3175 0.034 Uiso 1 calc R H9AB H 1.2517 0.9025 1.4284 0.034 Uiso 1 calc R C10A C 1.2900(4) 0.7271(2) 1.4001(2) 0.0293(6) Uani 1 d . H10A H 1.2538 0.7260 1.4599 0.035 Uiso 1 calc R H10B H 1.2367 0.6516 1.3486 0.035 Uiso 1 calc R O1C O -0.0380(3) 0.52354(18) 0.89407(16) 0.0376(5) Uani 1 d . O2C O -0.3817(2) 1.00456(16) 0.86769(14) 0.0327(5) Uani 1 d . H2C H -0.4291 1.0681 0.8751 0.049 Uiso 1 d R N1C N 0.4517(3) 0.2197(2) 0.88436(17) 0.0287(6) Uani 1 d . N2C N 0.2444(3) 0.61502(18) 0.87177(16) 0.0222(5) Uani 1 d . H2CA H 0.3707 0.6132 0.8643 0.027 Uiso 1 calc R N3C N 0.1370(3) 0.71201(19) 0.87217(16) 0.0226(5) Uani 1 d . C1C C 0.2825(4) 0.2468(2) 0.9227(2) 0.0319(7) Uani 1 d . H1C H 0.2301 0.1975 0.9508 0.038 Uiso 1 calc R C2C C 0.1826(4) 0.3435(2) 0.92262(19) 0.0267(6) Uani 1 d . H2CB H 0.0636 0.3576 0.9490 0.032 Uiso 1 calc R C3C C 0.2590(4) 0.4205(2) 0.88310(19) 0.0227(6) Uani 1 d . C4C C 0.4356(4) 0.3928(2) 0.8435(2) 0.0291(7) Uani 1 d . H4C H 0.4929 0.4409 0.8156 0.035 Uiso 1 calc R C5C C 0.5244(4) 0.2928(3) 0.8464(2) 0.0331(7) Uani 1 d . H5C H 0.6428 0.2755 0.8199 0.040 Uiso 1 calc R C6C C 0.1414(4) 0.5241(2) 0.88367(19) 0.0242(6) Uani 1 d . C7C C 0.2454(4) 0.8003(2) 0.8706(2) 0.0238(6) Uani 1 d . H7C H 0.3851 0.7962 0.8690 0.029 Uiso 1 calc R C8C C 0.1511(4) 0.9103(2) 0.8712(2) 0.0262(6) Uani 1 d . H8CA H 0.1833 0.9286 0.8168 0.031 Uiso 1 calc R H8CB H 0.2147 0.9755 0.9300 0.031 Uiso 1 calc R C9C C -0.0804(3) 0.9039(2) 0.86542(19) 0.0203(6) Uani 1 d . H9CA H -0.1465 0.8461 0.8028 0.024 Uiso 1 calc R H9CB H -0.1157 0.8768 0.9150 0.024 Uiso 1 calc R C10C C -0.1621(4) 1.0219(2) 0.8786(2) 0.0245(6) Uani 1 d . H10C H -0.1039 1.0795 0.9425 0.029 Uiso 1 calc R H10D H -0.1251 1.0513 0.8305 0.029 Uiso 1 calc R O1B O 0.9433(3) 1.35818(17) 1.10769(15) 0.0378(5) Uani 1 d . O2B O 1.2740(2) 0.87037(15) 1.13270(13) 0.0283(4) Uani 1 d . H2B H 1.3218 0.8071 1.1260 0.043 Uiso 1 d R N1B N 0.4409(3) 1.6565(2) 1.11181(17) 0.0298(6) Uani 1 d . N2B N 0.6607(3) 1.26471(18) 1.12719(15) 0.0229(5) Uani 1 d . H2BA H 0.5335 1.2662 1.1332 0.028 Uiso 1 calc R N3B N 0.7641(3) 1.16699(19) 1.12678(15) 0.0215(5) Uani 1 d . C1B C 0.3699(4) 1.5817(2) 1.1502(2) 0.0319(7) Uani 1 d . H1B H 0.2503 1.5972 1.1760 0.038 Uiso 1 calc R C2B C 0.4633(4) 1.4829(2) 1.1540(2) 0.0278(6) Uani 1 d . H2BB H 0.4069 1.4332 1.1808 0.033 Uiso 1 calc R C3B C 0.6430(4) 1.4598(2) 1.11692(19) 0.0223(6) Uani 1 d . C4B C 0.7195(4) 1.5367(2) 1.0784(2) 0.0263(6) Uani 1 d . H4B H 0.8411 1.5245 1.0540 0.032 Uiso 1 calc R C5B C 0.6149(4) 1.6314(2) 1.0763(2) 0.0300(6) Uani 1 d . H5B H 0.6675 1.6812 1.0486 0.036 Uiso 1 calc R C6B C 0.7624(4) 1.3558(2) 1.11815(19) 0.0248(6) Uani 1 d . C7B C 0.6507(4) 1.0741(2) 1.11508(19) 0.0230(6) Uani 1 d . H7B H 0.5090 1.0765 1.1095 0.028 Uiso 1 calc R C8B C 0.7386(4) 0.9618(2) 1.1101(2) 0.0250(6) Uani 1 d . H8BA H 0.6837 0.9011 1.0471 0.030 Uiso 1 calc R H8BB H 0.6935 0.9364 1.1588 0.030 Uiso 1 calc R C9B C 0.9742(4) 0.9707(2) 1.12552(19) 0.0216(6) Uani 1 d . H9BA H 1.0207 1.0002 1.0793 0.026 Uiso 1 calc R H9BB H 1.0301 1.0274 1.1901 0.026 Uiso 1 calc R C10B C 1.0562(4) 0.8518(2) 1.11370(19) 0.0217(6) Uani 1 d . H10E H 1.0088 0.8203 1.1587 0.026 Uiso 1 calc R H10F H 1.0074 0.7953 1.0483 0.026 Uiso 1 calc R O1D O 1.1707(2) 0.97854(16) 0.61651(15) 0.0364(5) Uani 1 d . O2D O 1.5057(2) 0.48004(15) 0.63122(13) 0.0320(5) Uani 1 d . H2D H 1.5724 0.4198 0.6197 0.048 Uiso 1 d R N1D N 0.6430(3) 1.2592(2) 0.61142(17) 0.0315(6) Uani 1 d . N2D N 0.8806(3) 0.86888(18) 0.61276(15) 0.0224(5) Uani 1 d . H2DA H 0.7499 0.8655 0.6114 0.027 Uiso 1 calc R N3D N 0.9885(3) 0.77235(19) 0.61300(15) 0.0222(5) Uani 1 d . C1D C 0.5522(4) 1.1486(3) 0.5729(2) 0.0323(7) Uani 1 d . H1D H 0.4139 1.1366 0.5442 0.039 Uiso 1 calc R C2D C 0.6511(4) 1.0505(2) 0.5730(2) 0.0303(6) Uani 1 d . H2DB H 0.5799 0.9749 0.5463 0.036 Uiso 1 calc R C3D C 0.8585(4) 1.0667(2) 0.61349(18) 0.0215(6) Uani 1 d . C4D C 0.9565(4) 1.1811(2) 0.6524(2) 0.0316(6) Uani 1 d . H4D H 1.0960 1.1950 0.6793 0.038 Uiso 1 calc R C5D C 0.8440(4) 1.2744(2) 0.6510(2) 0.0355(7) Uani 1 d . H5D H 0.9105 1.3512 0.6786 0.043 Uiso 1 calc R C6D C 0.9853(4) 0.9668(2) 0.61463(18) 0.0220(6) Uani 1 d . C7D C 0.8807(4) 0.6848(2) 0.61671(18) 0.0228(6) Uani 1 d . H7D H 0.7403 0.6877 0.6165 0.027 Uiso 1 calc R C8D C 0.9783(4) 0.5789(2) 0.6213(2) 0.0235(6) Uani 1 d . H8DA H 0.9051 0.5095 0.5685 0.028 Uiso 1 calc R H8DB H 0.9612 0.5701 0.6815 0.028 Uiso 1 calc R C9D C 1.2056(4) 0.5803(2) 0.6156(2) 0.0254(6) Uani 1 d . H9DA H 1.2257 0.5903 0.5562 0.030 Uiso 1 calc R H9DB H 1.2820 0.6472 0.6698 0.030 Uiso 1 calc R C10D C 1.2868(4) 0.4669(2) 0.6178(2) 0.0265(6) Uani 1 d . H10G H 1.2441 0.4486 0.6703 0.032 Uiso 1 calc R H10H H 1.2312 0.4019 0.5573 0.032 Uiso 1 calc R O1W O 0.6384(3) 0.64043(16) 0.82525(15) 0.0379(5) Uani 1 d . H1WA H 0.6012 0.5856 0.7696 0.057 Uiso 1 d R H1WB H 0.7603 0.6396 0.8530 0.057 Uiso 1 d R O3W O 1.2590(3) 1.24073(17) 1.17223(16) 0.0454(6) Uani 1 d . H3WA H 1.2393 1.2285 1.2227 0.068 Uiso 1 d R H3WB H 1.1505 1.2627 1.1478 0.068 Uiso 1 d R O2W O 0.4976(2) 0.85608(17) 0.67106(14) 0.0351(5) Uani 1 d . H2WA H 0.3950 0.8787 0.6429 0.053 Uiso 1 d R H2WB H 0.5250 0.9007 0.7308 0.053 Uiso 1 d R O4W O 0.4358(2) 1.05226(17) 1.30696(15) 0.0424(5) Uani 1 d . H4WA H 0.3483 1.0969 1.3326 0.064 Uiso 1 d R H4WB H 0.3498 1.0058 1.2575 0.064 Uiso 1 d R 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 O1A 0.0161(9) 0.0242(10) 0.0680(14) 0.0176(10) 0.0110(9) 0.0058(7) O2A 0.0259(10) 0.0307(11) 0.0843(17) 0.0258(11) 0.0097(10) 0.0103(8) N1A 0.0260(11) 0.0233(13) 0.0318(14) 0.0093(11) 0.0010(10) 0.0067(9) N2A 0.0134(10) 0.0178(12) 0.0309(13) 0.0101(10) 0.0075(9) 0.0063(8) N3A 0.0207(11) 0.0192(12) 0.0292(13) 0.0115(10) 0.0058(9) 0.0069(9) C1A 0.0175(12) 0.0225(15) 0.0340(16) 0.0081(13) 0.0044(11) 0.0057(10) C2A 0.0204(13) 0.0238(15) 0.0306(15) 0.0128(13) 0.0058(11) 0.0014(11) C3A 0.0208(13) 0.0152(13) 0.0156(13) 0.0016(11) 0.0007(10) 0.0010(10) C4A 0.0210(12) 0.0240(15) 0.0304(15) 0.0091(12) 0.0082(11) 0.0059(11) C5A 0.0301(14) 0.0208(15) 0.0351(16) 0.0140(13) 0.0041(12) 0.0003(11) C6A 0.0205(13) 0.0195(14) 0.0254(15) 0.0070(12) 0.0086(11) 0.0043(11) C7A 0.0207(13) 0.0228(16) 0.0307(15) 0.0108(13) 0.0068(11) 0.0067(11) C8A 0.0281(14) 0.0187(14) 0.0286(15) 0.0101(12) 0.0068(12) 0.0026(11) C9A 0.0295(14) 0.0246(15) 0.0342(16) 0.0135(13) 0.0093(12) 0.0069(11) C10A 0.0277(14) 0.0268(16) 0.0400(17) 0.0188(14) 0.0080(12) 0.0085(11) O1C 0.0239(10) 0.0383(12) 0.0666(15) 0.0327(11) 0.0193(10) 0.0130(9) O2C 0.0228(9) 0.0262(11) 0.0504(13) 0.0149(10) 0.0065(9) 0.0104(8) N1C 0.0284(13) 0.0207(13) 0.0384(14) 0.0117(12) 0.0069(11) 0.0080(10) N2C 0.0152(11) 0.0218(13) 0.0327(14) 0.0122(11) 0.0065(10) 0.0094(9) N3C 0.0242(11) 0.0216(13) 0.0256(13) 0.0114(11) 0.0059(9) 0.0106(10) C1C 0.0294(15) 0.0237(16) 0.0472(19) 0.0183(15) 0.0073(13) 0.0041(12) C2C 0.0227(13) 0.0235(15) 0.0343(17) 0.0104(13) 0.0069(12) 0.0038(11) C3C 0.0196(13) 0.0236(15) 0.0244(15) 0.0084(12) 0.0031(11) 0.0052(11) C4C 0.0295(14) 0.0289(16) 0.0349(17) 0.0157(14) 0.0120(13) 0.0093(12) C5C 0.0297(15) 0.0327(17) 0.0462(19) 0.0192(15) 0.0185(14) 0.0179(13) C6C 0.0248(14) 0.0257(16) 0.0241(16) 0.0108(13) 0.0049(12) 0.0095(12) C7C 0.0155(13) 0.0230(16) 0.0348(17) 0.0122(13) 0.0052(11) 0.0056(11) C8C 0.0216(13) 0.0242(16) 0.0348(17) 0.0134(13) 0.0044(12) 0.0043(11) C9C 0.0216(13) 0.0177(14) 0.0219(15) 0.0068(12) 0.0052(11) 0.0045(11) C10C 0.0204(13) 0.0232(15) 0.0309(16) 0.0103(13) 0.0064(11) 0.0038(11) O1B 0.0243(10) 0.0383(12) 0.0686(15) 0.0345(12) 0.0209(10) 0.0146(8) O2B 0.0181(8) 0.0183(10) 0.0487(13) 0.0118(9) 0.0059(8) 0.0086(7) N1B 0.0333(13) 0.0214(13) 0.0337(14) 0.0097(11) 0.0024(11) 0.0095(10) N2B 0.0166(11) 0.0262(13) 0.0327(14) 0.0168(11) 0.0076(10) 0.0103(9) N3B 0.0190(11) 0.0221(13) 0.0257(13) 0.0101(10) 0.0056(9) 0.0093(10) C1B 0.0310(15) 0.0340(18) 0.0338(17) 0.0130(15) 0.0110(13) 0.0133(13) C2B 0.0301(14) 0.0271(16) 0.0339(17) 0.0175(14) 0.0101(12) 0.0119(12) C3B 0.0235(13) 0.0170(15) 0.0258(16) 0.0078(13) 0.0023(11) 0.0045(11) C4B 0.0186(12) 0.0248(16) 0.0370(17) 0.0129(14) 0.0046(12) 0.0052(11) C5B 0.0310(15) 0.0191(15) 0.0415(18) 0.0140(14) 0.0047(13) 0.0006(12) C6B 0.0221(14) 0.0262(16) 0.0315(17) 0.0158(14) 0.0066(12) 0.0082(11) C7B 0.0154(12) 0.0286(17) 0.0284(15) 0.0136(13) 0.0048(11) 0.0070(11) C8B 0.0248(13) 0.0206(15) 0.0306(15) 0.0097(12) 0.0062(11) 0.0056(11) C9B 0.0235(13) 0.0192(14) 0.0232(14) 0.0096(12) 0.0036(11) 0.0016(10) C10B 0.0172(12) 0.0187(15) 0.0310(16) 0.0110(12) 0.0043(11) 0.0041(10) O1D 0.0178(9) 0.0336(12) 0.0649(14) 0.0249(11) 0.0101(9) 0.0085(8) O2D 0.0235(9) 0.0274(11) 0.0484(12) 0.0158(10) 0.0092(8) 0.0124(8) N1D 0.0269(12) 0.0277(14) 0.0463(16) 0.0188(12) 0.0101(11) 0.0128(10) N2D 0.0173(10) 0.0197(12) 0.0319(13) 0.0103(10) 0.0062(9) 0.0077(9) N3D 0.0204(11) 0.0199(13) 0.0264(13) 0.0089(10) 0.0023(9) 0.0071(10) C1D 0.0241(14) 0.0325(17) 0.0443(18) 0.0189(14) 0.0044(12) 0.0094(12) C2D 0.0240(13) 0.0235(15) 0.0418(18) 0.0124(13) 0.0009(12) 0.0005(11) C3D 0.0235(13) 0.0183(14) 0.0256(15) 0.0095(12) 0.0088(11) 0.0054(10) C4D 0.0228(13) 0.0259(16) 0.0481(18) 0.0168(14) 0.0041(12) 0.0048(11) C5D 0.0364(16) 0.0211(15) 0.0486(19) 0.0124(14) 0.0086(14) 0.0015(12) C6D 0.0198(13) 0.0184(15) 0.0269(15) 0.0071(12) 0.0041(11) 0.0024(11) C7D 0.0188(12) 0.0218(15) 0.0242(15) 0.0046(12) 0.0013(11) 0.0068(11) C8D 0.0223(13) 0.0182(15) 0.0280(15) 0.0060(12) 0.0053(11) 0.0025(10) C9D 0.0224(13) 0.0239(15) 0.0318(16) 0.0128(13) 0.0047(11) 0.0025(11) C10D 0.0249(14) 0.0236(15) 0.0319(16) 0.0108(13) 0.0047(12) 0.0095(11) O1W 0.0181(9) 0.0334(12) 0.0613(15) 0.0154(11) 0.0088(9) 0.0080(8) O3W 0.0242(10) 0.0503(14) 0.0781(17) 0.0399(13) 0.0156(10) 0.0109(9) O2W 0.0223(9) 0.0422(12) 0.0400(12) 0.0141(10) 0.0038(8) 0.0123(8) O4W 0.0162(9) 0.0400(12) 0.0530(13) -0.0038(10) 0.0057(8) 0.0012(8) 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' loop_ _citation_id _citation_doi _citation_year 1 10.1039/C8NJ01680A 2018 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C10A O2A H2A 109.6 C1A N1A C5A 116.6(2) N3A N2A H2AA 120.9 C6A N2A H2AA 120.9 C6A N2A N3A 118.22(19) C7A N3A N2A 115.4(2) N1A C1A H1A 118.1 N1A C1A C2A 123.7(2) C2A C1A H1A 118.1 C1A C2A H2AB 120.5 C3A C2A C1A 119.0(2) C3A C2A H2AB 120.5 C2A C3A C4A 117.7(2) C2A C3A C6A 124.2(2) C4A C3A C6A 118.1(2) C3A C4A H4A 120.4 C5A C4A C3A 119.2(2) C5A C4A H4A 120.4 N1A C5A C4A 123.8(2) N1A C5A H5A 118.1 C4A C5A H5A 118.1 O1A C6A N2A 123.9(2) O1A C6A C3A 119.3(2) N2A C6A C3A 116.8(2) N3A C7A H7A 119.8 N3A C7A C8A 120.4(2) C8A C7A H7A 119.8 C7A C8A H8AA 108.5 C7A C8A H8AB 108.5 C7A C8A C9A 115.3(2) H8AA C8A H8AB 107.5 C9A C8A H8AA 108.5 C9A C8A H8AB 108.5 C8A C9A H9AA 109.2 C8A C9A H9AB 109.2 H9AA C9A H9AB 107.9 C10A C9A C8A 112.1(2) C10A C9A H9AA 109.2 C10A C9A H9AB 109.2 O2A C10A C9A 108.5(2) O2A C10A H10A 110.0 O2A C10A H10B 110.0 C9A C10A H10A 110.0 C9A C10A H10B 110.0 H10A C10A H10B 108.4 C10C O2C H2C 109.3 C5C N1C C1C 116.8(2) N3C N2C H2CA 121.4 C6C N2C H2CA 121.4 C6C N2C N3C 117.20(19) C7C N3C N2C 115.0(2) N1C C1C H1C 118.3 N1C C1C C2C 123.3(3) C2C C1C H1C 118.3 C1C C2C H2CB 120.0 C1C C2C C3C 119.9(2) C3C C2C H2CB 120.0 C2C C3C C4C 116.9(2) C2C C3C C6C 117.7(2) C4C C3C C6C 125.4(2) C3C C4C H4C 120.6 C5C C4C C3C 118.9(3) C5C C4C H4C 120.6 N1C C5C C4C 124.1(2) N1C C5C H5C 117.9 C4C C5C H5C 117.9 O1C C6C N2C 123.1(2) O1C C6C C3C 120.3(2) N2C C6C C3C 116.6(2) N3C C7C H7C 119.6 N3C C7C C8C 120.8(2) C8C C7C H7C 119.6 C7C C8C H8CA 108.4 C7C C8C H8CB 108.4 C7C C8C C9C 115.3(2) H8CA C8C H8CB 107.5 C9C C8C H8CA 108.4 C9C C8C H8CB 108.4 C8C C9C H9CA 109.1 C8C C9C H9CB 109.1 H9CA C9C H9CB 107.8 C10C C9C C8C 112.5(2) C10C C9C H9CA 109.1 C10C C9C H9CB 109.1 O2C C10C C9C 107.8(2) O2C C10C H10C 110.1 O2C C10C H10D 110.1 C9C C10C H10C 110.1 C9C C10C H10D 110.1 H10C C10C H10D 108.5 C10B O2B H2B 109.7 C1B N1B C5B 116.0(2) N3B N2B H2BA 120.7 C6B N2B H2BA 120.7 C6B N2B N3B 118.64(19) C7B N3B N2B 115.4(2) N1B C1B H1B 117.9 N1B C1B C2B 124.1(2) C2B C1B H1B 117.9 C1B C2B H2BB 120.8 C1B C2B C3B 118.4(3) C3B C2B H2BB 120.8 C2B C3B C6B 123.6(2) C4B C3B C2B 118.2(2) C4B C3B C6B 118.2(2) C3B C4B H4B 120.3 C5B C4B C3B 119.5(2) C5B C4B H4B 120.3 N1B C5B C4B 123.8(3) N1B C5B H5B 118.1 C4B C5B H5B 118.1 O1B C6B N2B 123.7(2) O1B C6B C3B 119.2(2) N2B C6B C3B 117.1(2) N3B C7B H7B 119.2 N3B C7B C8B 121.6(2) C8B C7B H7B 119.2 C7B C8B H8BA 108.7 C7B C8B H8BB 108.7 C7B C8B C9B 114.4(2) H8BA C8B H8BB 107.6 C9B C8B H8BA 108.7 C9B C8B H8BB 108.7 C8B C9B H9BA 109.1 C8B C9B H9BB 109.1 H9BA C9B H9BB 107.9 C10B C9B C8B 112.4(2) C10B C9B H9BA 109.1 C10B C9B H9BB 109.1 O2B C10B C9B 107.91(19) O2B C10B H10E 110.1 O2B C10B H10F 110.1 C9B C10B H10E 110.1 C9B C10B H10F 110.1 H10E C10B H10F 108.4 C10D O2D H2D 120.6 C1D N1D C5D 117.1(2) N3D N2D H2DA 120.8 C6D N2D H2DA 120.8 C6D N2D N3D 118.41(19) C7D N3D N2D 114.83(19) N1D C1D H1D 118.1 N1D C1D C2D 123.8(2) C2D C1D H1D 118.1 C1D C2D H2DB 120.6 C1D C2D C3D 118.8(3) C3D C2D H2DB 120.6 C2D C3D C6D 123.9(2) C4D C3D C2D 118.2(2) C4D C3D C6D 117.9(2) C3D C4D H4D 120.5 C3D C4D C5D 119.0(2) C5D C4D H4D 120.5 N1D C5D C4D 123.0(3) N1D C5D H5D 118.5 C4D C5D H5D 118.5 O1D C6D N2D 124.8(2) O1D C6D C3D 119.8(2) N2D C6D C3D 115.4(2) N3D C7D H7D 119.9 N3D C7D C8D 120.2(2) C8D C7D H7D 119.9 C7D C8D H8DA 108.4 C7D C8D H8DB 108.4 C7D C8D C9D 115.7(2) H8DA C8D H8DB 107.4 C9D C8D H8DA 108.4 C9D C8D H8DB 108.4 C8D C9D H9DA 109.4 C8D C9D H9DB 109.4 H9DA C9D H9DB 108.0 C10D C9D C8D 111.1(2) C10D C9D H9DA 109.4 C10D C9D H9DB 109.4 O2D C10D C9D 109.5(2) O2D C10D H10G 109.8 O2D C10D H10H 109.8 C9D C10D H10G 109.8 C9D C10D H10H 109.8 H10G C10D H10H 108.2 H1WA O1W H1WB 114.6 H3WA O3W H3WB 109.5 H2WA O2W H2WB 109.5 H4WA O4W H4WB 95.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1A C6A 1.234(3) O2A H2A 0.8200 O2A C10A 1.410(3) N1A C1A 1.327(3) N1A C5A 1.344(3) N2A H2AA 0.8600 N2A N3A 1.394(3) N2A C6A 1.334(3) N3A C7A 1.273(3) C1A H1A 0.9300 C1A C2A 1.389(3) C2A H2AB 0.9300 C2A C3A 1.384(3) C3A C4A 1.386(4) C3A C6A 1.504(3) C4A H4A 0.9300 C4A C5A 1.374(3) C5A H5A 0.9300 C7A H7A 0.9300 C7A C8A 1.483(3) C8A H8AA 0.9700 C8A H8AB 0.9700 C8A C9A 1.527(3) C9A H9AA 0.9700 C9A H9AB 0.9700 C9A C10A 1.513(3) C10A H10A 0.9700 C10A H10B 0.9700 O1C C6C 1.221(3) O2C H2C 0.8200 O2C C10C 1.434(3) N1C C1C 1.336(3) N1C C5C 1.323(3) N2C H2CA 0.8600 N2C N3C 1.396(3) N2C C6C 1.352(3) N3C C7C 1.273(3) C1C H1C 0.9300 C1C C2C 1.368(4) C2C H2CB 0.9300 C2C C3C 1.389(4) C3C C4C 1.391(3) C3C C6C 1.502(4) C4C H4C 0.9300 C4C C5C 1.379(4) C5C H5C 0.9300 C7C H7C 0.9300 C7C C8C 1.492(3) C8C H8CA 0.9700 C8C H8CB 0.9700 C8C C9C 1.517(3) C9C H9CA 0.9700 C9C H9CB 0.9700 C9C C10C 1.506(3) C10C H10C 0.9700 C10C H10D 0.9700 O1B C6B 1.230(3) O2B H2B 0.8202 O2B C10B 1.416(3) N1B C1B 1.341(3) N1B C5B 1.343(3) N2B H2BA 0.8600 N2B N3B 1.390(3) N2B C6B 1.329(3) N3B C7B 1.268(3) C1B H1B 0.9300 C1B C2B 1.385(4) C2B H2BB 0.9300 C2B C3B 1.387(4) C3B C4B 1.377(3) C3B C6B 1.518(3) C4B H4B 0.9300 C4B C5B 1.372(4) C5B H5B 0.9300 C7B H7B 0.9300 C7B C8B 1.483(3) C8B H8BA 0.9700 C8B H8BB 0.9700 C8B C9B 1.532(3) C9B H9BA 0.9700 C9B H9BB 0.9700 C9B C10B 1.521(3) C10B H10E 0.9700 C10B H10F 0.9700 O1D C6D 1.224(3) O2D H2D 0.8469 O2D C10D 1.424(3) N1D C1D 1.328(4) N1D C5D 1.345(3) N2D H2DA 0.8600 N2D N3D 1.396(3) N2D C6D 1.338(3) N3D C7D 1.276(3) C1D H1D 0.9300 C1D C2D 1.380(3) C2D H2DB 0.9300 C2D C3D 1.386(3) C3D C4D 1.382(4) C3D C6D 1.504(3) C4D H4D 0.9300 C4D C5D 1.383(4) C5D H5D 0.9300 C7D H7D 0.9300 C7D C8D 1.478(3) C8D H8DA 0.9700 C8D H8DB 0.9700 C8D C9D 1.518(3) C9D H9DA 0.9700 C9D H9DB 0.9700 C9D C10D 1.504(3) C10D H10G 0.9700 C10D H10H 0.9700 O1W H1WA 0.8517 O1W H1WB 0.8499 O3W H3WA 0.8499 O3W H3WB 0.8503 O2W H2WA 0.8499 O2W H2WB 0.8507 O4W H4WA 0.8496 O4W H4WB 0.8574 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 O2A H2A N1A 0.82 2.07 2.882(3) 174.0 1_645 N2A H2AA O4W 0.86 1.99 2.809(3) 159.7 . O2C H2C N1C 0.82 2.00 2.816(3) 176.5 1_465 N2C H2CA O1W 0.86 2.00 2.833(3) 162.9 . O2B H2B N1B 0.82 1.97 2.792(3) 179.0 1_645 N2B H2BA O3W 0.86 2.04 2.869(3) 162.8 1_455 O2D H2D N1D 0.85 1.98 2.791(2) 158.7 1_645 N2D H2DA O2W 0.86 2.03 2.821(2) 152.5 . O1W H1WA O2D 0.85 2.00 2.838(3) 170.1 1_455 O1W H1WB O1C 0.85 2.16 2.873(2) 141.8 1_655 O1W H1WB N3C 0.85 2.54 3.275(3) 144.5 1_655 O3W H3WA O1A 0.85 2.45 3.293(3) 171.3 . O3W H3WB O1B 0.85 1.99 2.814(3) 163.9 . O3W H3WB N3B 0.85 2.69 3.256(3) 125.6 . O2W H2WA O1D 0.85 2.03 2.850(2) 161.4 1_455 O2W H2WB O2C 0.85 1.97 2.819(3) 174.1 1_655 O4W H4WA O1A 0.85 2.00 2.831(2) 167.3 1_455 O4W H4WB O2B 0.86 1.97 2.768(3) 153.5 1_455 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 N1A C1A C2A C3A 1.2(4) N2A N3A C7A C8A -178.6(2) N3A N2A C6A O1A 2.4(4) N3A N2A C6A C3A -176.8(2) N3A C7A C8A C9A 1.2(4) C1A N1A C5A C4A 0.0(4) C1A C2A C3A C4A -1.0(4) C1A C2A C3A C6A 176.5(2) C2A C3A C4A C5A 0.4(4) C2A C3A C6A O1A -160.3(2) C2A C3A C6A N2A 18.9(4) C3A C4A C5A N1A 0.2(4) C4A C3A C6A O1A 17.2(4) C4A C3A C6A N2A -163.6(2) C5A N1A C1A C2A -0.7(4) C6A N2A N3A C7A -178.3(2) C6A C3A C4A C5A -177.3(2) C7A C8A C9A C10A 167.5(2) C8A C9A C10A O2A 178.8(2) N1C C1C C2C C3C -1.4(4) N2C N3C C7C C8C -179.8(2) N3C N2C C6C O1C 0.3(4) N3C N2C C6C C3C -180.0(2) N3C C7C C8C C9C -4.8(4) C1C N1C C5C C4C -0.6(4) C1C C2C C3C C4C 1.0(4) C1C C2C C3C C6C 179.1(3) C2C C3C C4C C5C -0.5(4) C2C C3C C6C O1C -18.8(4) C2C C3C C6C N2C 161.5(2) C3C C4C C5C N1C 0.3(5) C4C C3C C6C O1C 159.1(3) C4C C3C C6C N2C -20.6(4) C5C N1C C1C C2C 1.1(4) C6C N2C N3C C7C 173.2(2) C6C C3C C4C C5C -178.5(3) C7C C8C C9C C10C 173.0(2) C8C C9C C10C O2C 177.5(2) N1B C1B C2B C3B 0.8(5) N2B N3B C7B C8B 178.1(2) N3B N2B C6B O1B 1.3(4) N3B N2B C6B C3B 178.8(2) N3B C7B C8B C9B 3.1(4) C1B N1B C5B C4B -0.6(4) C1B C2B C3B C4B 0.1(4) C1B C2B C3B C6B 178.9(3) C2B C3B C4B C5B -1.2(4) C2B C3B C6B O1B -161.3(3) C2B C3B C6B N2B 21.1(4) C3B C4B C5B N1B 1.5(4) C4B C3B C6B O1B 17.5(4) C4B C3B C6B N2B -160.1(2) C5B N1B C1B C2B -0.6(4) C6B N2B N3B C7B -165.7(2) C6B C3B C4B C5B 180.0(3) C7B C8B C9B C10B -176.5(2) C8B C9B C10B O2B -178.0(2) N1D C1D C2D C3D -1.4(4) N2D N3D C7D C8D -177.6(2) N3D N2D C6D O1D 0.0(4) N3D N2D C6D C3D 179.6(2) N3D C7D C8D C9D -3.2(4) C1D N1D C5D C4D 0.3(4) C1D C2D C3D C4D 0.3(4) C1D C2D C3D C6D -177.6(2) C2D C3D C4D C5D 1.0(4) C2D C3D C6D O1D 152.5(3) C2D C3D C6D N2D -27.1(4) C3D C4D C5D N1D -1.4(4) C4D C3D C6D O1D -25.4(4) C4D C3D C6D N2D 155.1(2) C5D N1D C1D C2D 1.2(4) C6D N2D N3D C7D 176.2(2) C6D C3D C4D C5D 179.0(2) C7D C8D C9D C10D -178.2(2) C8D C9D C10D O2D -168.8(2)